Title of Invention	INSECTICIDAL ANTHRANILAMIDES
Abstract	We claim: 1. A method for controlling arthropods comprising contacting the arthropods 01 their environment with an arthropodicidally effective amount of a compound of Formula 1, its TV-oxide or agriculturally suitable salts wherein A and B are independently 0 or S; each J is independently a phenyl or naphthyl group substituted with 1 to 2 R-"" and optionally substituted with 1 to 3 R6; or each J is independently a 5- or 6-membered heteroaromatic ring or an aromatic 8-, 9- or I O-membered fused heterobicyclic ring system wherein-each ring or ring system is optionally substituted with 1 to 4 R7; n is 1 to 4, R1 is H; or CrC() alkyl, C2-C6 alkenyl, C2-C6 alkynyl or C3~C6 cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, N02, hydroxy. CrC4 alkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C[-C4 alkylsulfonyl, C2~C4 alkoxycarbonyl, CpC4 alkylamino. C2-C^ dialkylamino and C^-C^, cycloalkylamino; or R1 is C2-Q, alkylcarbonyl, C2-C(y alkoxycarbonyl, C2-CV> alkylaminocarbonyl. CrC8 dialkylaminocarbonyl or C(=A)J; R2 is H, C,-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, CrC4 alkoxy, C\-C+ alkylamino, C2-Cx dialkylamino, C^-Q, cycloalkylamino. C2-C6 alkoxycarbonyl or C2-C6 alkylcarbonyl; R3 is H; G; CrC6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-Cf) cycloalkyl, each optionally substituted with one or more substituents selected from the group consisting of halogen, G, CN, N02, hydroxy, CrC4 alkoxy, CrC4 haloalkoxv, C y-C j,alkylthio, Ci,-C4alkylsulfinyl. Gj^C^alkylsulfonyL CrC^ alkoxycarbonyl, C2-C6 alkylcarbonyl, C3-C6 trialkylsilyl, and a phenyl, phenoxy or 5- or 6-membered heteroaromatic ring, each ring optionally substituted with one to three substituents independently selected from the group consisting of CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, CrC4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyi, halogen, CN, NO2, C1-C4 alkoxy, C1-C4 haloalkoxy, CpC4 alkylthio, CrC4 alkylsulfinyl, CpC4 alkylsulfonyl, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C3-C6 (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl and C3-Q3 trialkylsilyl; Q-C4 alkoxy; Ci-C4 alkylamino, C2-C8 dialkylamino; C3-Q, cycloalkylamino; C2-C^ alkoxycarbonyl or C2-Q, alkylcarbonyl; or R2 and R' can be taken together with the nitrogen to which they are attached to form a ring containing 2 to 6 atoms of carbon and optionally one additional atom o\' nitrogen, sulfur or oxygen, said ring may be optionally substituted with 1 to 4 substituents selected from the group consisting of Ci-C2 alkyl, halogen. CN, N02 and C1-C2 alkoxy; G is a 5- or 6-membered nonaromatic carbocyclic or heterocyclic ring, optionally including one or two ring members selected from the group consisting of C( 0). SO or S(0)2 and optionally substituted with 1 to 4 substituents selected from the group consisting of Ci-C2 alkyl, halogen, CN, N02 and Cj-C2 alkoxy. each R~* is

Title of Invention

INSECTICIDAL ANTHRANILAMIDES

Abstract

We claim: 1. A method for controlling arthropods comprising contacting the arthropods 01 their environment with an arthropodicidally effective amount of a compound of Formula 1, its TV-oxide or agriculturally suitable salts wherein A and B are independently 0 or S; each J is independently a phenyl or naphthyl group substituted with 1 to 2 R-"" and optionally substituted with 1 to 3 R6; or each J is independently a 5- or 6-membered heteroaromatic ring or an aromatic 8-, 9- or I O-membered fused heterobicyclic ring system wherein-each ring or ring system is optionally substituted with 1 to 4 R7; n is 1 to 4, R1 is H; or CrC() alkyl, C2-C6 alkenyl, C2-C6 alkynyl or C3~C6 cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, N02, hydroxy. CrC4 alkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C[-C4 alkylsulfonyl, C2~C4 alkoxycarbonyl, CpC4 alkylamino. C2-C^ dialkylamino and C^-C^, cycloalkylamino; or R1 is C2-Q, alkylcarbonyl, C2-C(y alkoxycarbonyl, C2-CV> alkylaminocarbonyl. CrC8 dialkylaminocarbonyl or C(=A)J; R2 is H, C,-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, CrC4 alkoxy, C\-C+ alkylamino, C2-Cx dialkylamino, C^-Q, cycloalkylamino. C2-C6 alkoxycarbonyl or C2-C6 alkylcarbonyl; R3 is H; G; CrC6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-Cf) cycloalkyl, each optionally substituted with one or more substituents selected from the group consisting of halogen, G, CN, N02, hydroxy, CrC4 alkoxy, CrC4 haloalkoxv, C y-C j,alkylthio, Ci,-C4alkylsulfinyl. Gj^C^alkylsulfonyL CrC^ alkoxycarbonyl, C2-C6 alkylcarbonyl, C3-C6 trialkylsilyl, and a phenyl, phenoxy or 5- or 6-membered heteroaromatic ring, each ring optionally substituted with one to three substituents independently selected from the group consisting of CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, CrC4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyi, halogen, CN, NO2, C1-C4 alkoxy, C1-C4 haloalkoxy, CpC4 alkylthio, CrC4 alkylsulfinyl, CpC4 alkylsulfonyl, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C3-C6 (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl and C3-Q3 trialkylsilyl; Q-C4 alkoxy; Ci-C4 alkylamino, C2-C8 dialkylamino; C3-Q, cycloalkylamino; C2-C^ alkoxycarbonyl or C2-Q, alkylcarbonyl; or R2 and R' can be taken together with the nitrogen to which they are attached to form a ring containing 2 to 6 atoms of carbon and optionally one additional atom o\' nitrogen, sulfur or oxygen, said ring may be optionally substituted with 1 to 4 substituents selected from the group consisting of Ci-C2 alkyl, halogen. CN, N02 and C1-C2 alkoxy; G is a 5- or 6-membered nonaromatic carbocyclic or heterocyclic ring, optionally including one or two ring members selected from the group consisting of C( 0). SO or S(0)2 and optionally substituted with 1 to 4 substituents selected from the group consisting of Ci-C2 alkyl, halogen, CN, N02 and Cj-C2 alkoxy. each R~* is

Full Text	FORM 2 . THE PATENTS ACT 1970 [39 OF 1970] COMPLETE SPECIFICATION [See Section 10] "INSECTICIDAL ANTHRANILAMIDES" E.I. DU PONT DE NEMOURS AND COMPANY, a corporation organized and existing under the laws of the State of Delaware, of 1007 Market Street, Wilmington, Delaware 19898, United States of America, The following specification particularly describes and ascertains the nature of the invention and the manner in which it is to be performed:- WO 01/70671 PCT7US01/09338 TITLE INSECTICIDAL ANTHRANILAMIDES BACKGROUND OF THE INVENTION This invention relates to certain anthranilamides, their iV-oxides, agriculturally 5 suitable salts and compositions, and methods of their use as arthropodicides in both agronomic and nonagronomic environments. The control of arthropod pests is extremely important in achieving high crop efficiency. Arthropod damage to growing and stored agronomic crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. The control 10 of arthropod pests in forestry, greenhouse crops, ornamentals, nursery crops, stored food and fiber products, livestock, household, and public and animal health is also important. Many products are commercially available for these purposes, but the need continues for new compounds that are more effective, less costly, less toxic, environmentally safer or have different modes of action. 15 NL 9202078 discloses 7V-acyl anthranilic acid derivatives of Formula i as insecticides wherein, inter alia, X is a direct bond; 20 SUMMARY OF THE INVENnON This invention pertains to a method for controlling arthropods comprising contacting 25 the arthropods or their environment with an arthropodicidally effective amount of a compound of Formula 1, its N-oxide or agriculturally suitable salts WO 01/70671 PCT/US01/09338 wherein A and B are independently 0 or S; each J is independently a phenyl or naphthyl group substituted with 1 to 2 R5 and 5 optionally substituted with 1 to 3 R6; or each J is independently a 5- or 6-membered heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system wherein each ring or ring system is optionally substituted with 1 to 4 R7; n is 1 to 4; 10 RMsHjor alkyl, alkenyl, alkynylor cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, hydroxy, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkoxycarbonyl, alkylamino, dialkylamino and cycloalkylamino; or 15 R1 is alkylcarbonyl, alkoxycarbonyl, alkylaminocarbqnyl, dialkylarninocarbonyl or R2isH, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, alkylamino, dialkylamino, C3-C6 cycloalkylamino, C2~C6 alkoxycarbonyl or alkylcarbonyl; 20 R3 is H; G; alkyl, alkenyl, alkynyl, cycloalkyl, each optionally substituted with one or more substituents selected from the group consisting of halogen, G, CN, NO2, hydroxy, C1-C4 alkoxy, CyC^ haloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkoxycarbonyl, C2-C6 alkylcarbonyl, trialkylsilyl, or a phenyl, phenoxy 25 or 5- or 6-membered heteroaromatic ring, each ring optionally substituted with one to three substituents independently selected from the group consisting of Cj-C4 alkyl, alkenyl, C2-C4 alkynyl,cycloalkyl, (VC4 haloalkyl, C2- C4 haloalkenyl, haloalkynyl, C^-C^ halocycloalkyl, halogen, CN, NO2, alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, alkylsulfinyl, C1-C4 30 alkylsulfonyl, alkylamino,dialkylamino, cycloalkylamino, WO 01/70671 PCT/US01/09338 (alkyl)cycloalkylarnino, alkylcarbonyl, alkoxycarbonyl, C2- Cg alkylarninocarbonyl, dialkylaminocarbonyl or trialkylsilyl; C.r C4 alkoxy; alkylamino; dialkylamino; C3-Cg cycloalkylamino; C2- Cg alkoxycarbonyl or C2-C6 alkylcarbonyl; or 5 R2 and R3 can be taken together with the nitrogen to which they are attached to form a ring containing 2 to 6 atoms of carbon and optionally one additional atom of nitrogen, sulfur or oxygen, said ring may be optionally substituted with 1 to 4 substituents selected from the group consisting of C1-C2 alkyl, halogen, CN, N02 and CyC2 alkoxy; 10 G is a 5- or 6-membered nonaromatic carbocyclic or heterocyclic ring, optionally including one or two ring members selected from the group consisting of C(=0), SO or S(0)2 and optionally substituted with 1 to 4 substituents selected from the group consisting of alkyl, halogen, CN, N02 and Cp^ alkoxy; each R4 is independently H, CrC6 alkyl, C^-Cg alkenyl, C2-C6 alkynyl, C3-C6 15 cycloalkyl, CrC6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C6 . halocycloalkyl, halogen, CN, N02, hydroxy, Cj-C/j. alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, CrC4 alkylsulfonyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, C2-C4 haloalkylsulfonyl, Cj-C^ alkylamino, C2-C8 oUalkylamino, C3-Cg cycloalkylamino, or C3-C6 trialkylsilyl; or 20 each R4 is independently phenyl, ben2yl or phenoxy,* each optionally substituted with CrC4 alkyl, C2-C4 alkenyl, ilkynyl, C3-C6 cycloalkyl, CrC4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, halocycloalkyl, halogen, CN, N02, alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, 0^- C4 alkylsulfonyl, C1-C4 alkylamino, dialkylamino, C3-C6 25 cycloalkylamino, C3-Cg (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylarninocarbonyl, C3-Cg m'alkylaminocarbonyl or C3-Cg trialkylsilyl; each R5 is independently alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, CrC6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C6 30 halocycloalkyl, halogen, CN, C02H, CONH2, N02, hydroxy, CrC6 alkoxy, CrC6 haloalkoxy, CrC6 alkylthio, CrC6 alkylsulfinyl, CrCg alkylsulfonyl, Cj-Cg haloalkylthio, haloalkylsulfinyl, Ci-Cg haloalkylsulfonyl, C^Cg alkylamino, C2-C12 dialkylamino, or C3-Cg cycloallcylarmno, C2-C6 alkylcarbonyl, C2-Cg alkoxycarbonyl, C2-Cg allcylaminocarbonyl, C3-Cg 35dialkylarninocarbonyl,trialkylsilyl; or when attached to adjacent carbon atoms can be taken together as WO 01/70671 PCT/US01/09338 each R6 is independently H, halogen, alkyl, alkenyL alkynyl, C3- Cg cycloalkyl, alkoxy or alkoxycarbonyl; or each R6 is independently a phenyl, benzyl, phenoxy, 5- or 6-membered heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic 5 ring system, each ring optionally substituted with one to three substituents independently selected from the group consisting of CVC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, CrC4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, N02, Ci~C4 alkoxy, C^-C^ haloalkoxy, Cj-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 10 altylamino, C2-Cg malkylatnino, C3-C6 cycloalkylamhio, C3-C6 (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-Cg alkoxycarbonyl, C2-Cg alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl or C3-C6 trialkylsilyl; each R7 is independently alkenyl, alkynyl, C3-C6 cycloalkyl, Cj-Cg haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C6 15 halocycloalkyl, halogen, CN, C02H, CONH2,N02, hydroxy, CpC4 alkoxy, CrC4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, CrC4 haloalkylthio, CrC4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, (VC4 alkylamino, C^-Cg dialkylamino, C3-Cg cycloalkylamino, C2-C6 alkylcarbonyl, C2-C6 alkoxycarbonyl, alkylaminocarbonyl,dialkylaminocarbonyl, 20 C3-C6 trialkylsilyl; or each R7 is independently a phenyl, benzyl, benzoyl, phenoxy, 5- or 6-membered heteroaromatic ring or an aromatic 8-, 9- or lOrmembered fused heterobicyclic ring system, each ring optionally substituted with one to three substituents independently selected from the group consisting of C1-C4 alkyl, C2-C4 alkenyl, 25 C2-C4 alkynyl, C3-C6 cycloalkyl, CrC4 haloalkyl, C^^ haloalkenyl, CVQ haloalkynyl, C3-C6 halocycloalkyl, halogen, alkoxy, CrC4 haloalkoxy, CrC4 alkylthio, CVC4 alkylsulfinyl, CVC4 alkylsulfonyl, C1-C4 alkylamino, C2-Cg dialkylamino, C3-C6 cycloalkylamino, C3-C6 (alkyl)cycloallqdamino, C2-C4 alkylcarbonyl, C2-C^ alkoxycarbonyl, C2-C6 30 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl or C3-C6 trialkylsilyl; provided that (1) when A and B are both alkyL R3 is H or CrC3 alkyl and R4 is H, halogen, alkyl, phenyl, hydroxy or C^-Cg alkoxy, then one R5 is other than halogen, C^Cg alkyl, hydroxy or C^-Cg alkoxy; or 35 (2) J is other than an optionally substituted 1,2,3-thiadiazole. This invention also pertains to compounds of formula 1, their N-oxides and agriculturally suitable salts WO 01/70671PCT/US01/09338 wherein A and B are independently 0 or S; each J is independently a phenyl or naphthyl group substituted with 1 to 2 R5 and [ , 5 optionally substituted with 1 to 3 R6; , or each J is independently a 5- or 6-membered heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system wherein each ring or ring system is optionally substituted with 1 to 4 R7; n is 1 to 4; 10 R]isH;or alkyl, alkenyl, C2-C6 alkynyl or C3-C6 cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, hydroxy, alkoxy, C\-C^ alkylthio, C1-C4 alkylsulfinyl, C\-C4 alkylsulfonyl, alkoxycarbonyl, C! -C4 alkylamino, C2-Cg dialkylarnino and C3-Cg cycloalkylarnino; or 15 R1 is C2-Cg alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-Cg alkylarninocarbbnyl, C3-Cg &altylaminocarbonyl or C(=A)J; R2 is H, CrC6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, CrC4 alkoxy, CyC$ alkylamino, C^-Cg dialkylarnino, C3-C6 cycloalkylarnino, C2-C6 alkoxycarbonyl or C^-Cg alkylcarbonyl; 20 R3 is H; CrC6 alkyl, C2-C6 alkenyl, C^-Cg alkynyl, C3-C6 cycloalkyl, each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, N02, hydroxy, C1-C4 alkoxy, C1-C4 haloalkoxy, Cp C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C2-Cg alkoxycarbonyl, . C2-C6 alkylcarbonyl, C3-C5 trialkylsilyl, or a phenoxy ring optionally substituted 25 with one to three substituents independently selected from the group consisting of CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, CrC4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, N02, CrC4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylamino, C2-Cs dialkylarnino, C3- 30 C6 cycloalkylarnino, C3-C6 (allqrl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-C6 WO 01/70671 PCT/US01/09338 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl or C3- Gg trialkylsttyl; 0^04 alkoxy, C1-C4 alkylamino; C2-Cg dialkylamino; C3-C6 cycloalkylamino; C2-Cg alkoxycarbonyl or C2-Cg alkylcarbonyl; or R.2 and R3 can be taken together with the nitrogen to which they are attached to form 5 ■ a ring containing 2 to 6 atoms of carbon and optionally one additional atom of nitrogen, sulfur or oxygen, said ring may be optionally substituted with 1 to 4 substiruents selected from the group consisting of Ci-C2 alkyl, halogen, CN, N02 and Cj-02 alkoxy; each R4 is independently H, C^Cg alkyl, C2-Cg alkenyl, C2-Cg alkynyl, C3-C6 10 cycloalkyl, CrC6 haloalkyl, C2-Cg haloalkenyl, C^-Cg haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, N02, hydroxy, C1-C4 alkoxy, CJ-C4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, Ci-Q^ alkylsulfonyl, CrC4 haloalkylthio, CJ-C4 haloalkylsulfinyl, C^^ haloalkylsulfonyl, Q-C4 alkylamino, C2~C8 dialkylamino, C3-C6 cycloallcylamino, or C3-Cg trialkylsilyl; or 15 each R4 is independently phenyl, benzyl or phenoxy, each optionally substituted with CrC4 alkyl, CVC4 alkenyl, C2-C4 alkynyl, C3-C6cycloalkyl, CrC4haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, N02, CrC4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, Cr C4 alkylsulfonyl, C1-C4 allcylamino, C2-C8 dialkylamino, C3-C6 20 cycloalkylamino, C3-Cg (alkyl)cyctoalkylamino, C2-C4 alkylcarbonyl, C2-C5 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl or C3-C6 trialkylsilyl; each R5 is independently CrC6 haloalkyl, C2-C6 haloalkenyl, C2-Cg haloalkynyl, C3-Cg halocycloalkyl, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, 25 CrC4 alkylsulfonyl, C!-C4 haloalkylthio, CrC4 haloalkylsulfinyl, CrC4 haloalkylsulfonyl, CN, N02, CrC4 alkoxycarbonyl, CJ-C4 alkylamino, C2-C8 dialkylamino, C3-Cg cycloallcylarnino, C^-Cg alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, or C3-Cg dialkylaminocarbonyl; or (R5)2 attached to adjacent carbon atoms can be taken together as -OCF20-, 30 -CF2CF20-, or -OCF2CF20-; each R6 is independently H, halogen, Cj-Cg alkyl, C2-Cg alkenyl, C2-C6 alkynyl, C3- C6 cycloalkyl, C1-C4 alkoxy or C2-C4 alkoxycarbonyl; or each R6 is independently a phenyl, benzyl, phenoxy, 5- or 6-membered heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic 35 ring system, each ring optionally substituted with one to three substiruents independently selected from the group consisting of C1-C4 alkyL C2-C4 alkenyl, C2~C4 alkynyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 , hai™iVvT.vi r~.r, haW.™inniVyi9 haloaen. CN.NOo. Cn-G. alkoxv. G-C WO 01/70671 PCT/US01/09338 haloalkoxy, Ci-C4 alkylthio, CrC4 alkylsulfinyl, CrC4 alkylsulfonyl, CrC4 alkylamino, C2-Cg dialkylamino, C3-C6 cycloaUsylamino, C3-Cg (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-Cg alkoxycarbonyl, Cj-Cg alkylarninocarbonyl, C3-C8 dialkylaminocarbonyl or C3-C6 trialkylsilyl; 5 each. R7 is independently H, CrC6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, Cj-Cg haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, C02H, CONH2, N02, hydroxy, CrC4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio, C1-C4 alkylsulfinyl, CrC4 alkylsulfonyl, C1-C4 haloalkylthio, CrC4 haloalkylsulfinyl, CrC4 haloalkylsulfonyl, C1-C4 10 alkylamino, C2-Cg dialkylamino, C3-C6 cycloalkylarnino, C2-Cg alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl, C3-Cg trialkylsilyl; or each R7 is independently a phenyl,.benzyl, benzoyl, phenoxy or 5- or 6-membered ■ heteroaromatic ring 8-, 9- or 10-membered fused heterobicyclic ring system, 15 each ring optionally substituted with one to three substituents independently selected from the group consisting of C j -C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, CrC4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3- C6 halocycloalkyl, halogen, CN, N02, GrC4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio, Cj-C4 alkylsulfinyl, Ci-C4 alkylsulfonyl, C}-^ alkylamino, C^Cg 20 o^alkylarnino, C3-C6 cycloalkylamino, C3-C6 (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-Cg alkoxycarbonyl, C^-Cg alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl or C3-Cg trialkylsilyl; provided that (i) at least one R4 and at least one R7 are other than H; 25 (ii) J is other than an optionally substituted 1,2,3-thiadiazole; (iii) when J is an optionally substituted pyridine and R2 is H, R3 is other than H or CH3; (iv) when J is an optionally substituted pyridine, then R7 cannot be CONH2, C2-C6 alkylaminocarbonyl or C3-Cg dialkylaminocarbonyl; 30 (v) when J is an optionally substituted pyrazole, tetrazole or pyrirnidine, then R2 and R3 cannot both be hydrogen. This invention also pertains to arthropodicidal compositions comprising an arthropodicidally effective amount of a compound of Formula 1 and at least one additional component selected from the group consisting of surfactants, solid diluents and liquid 35 djhjgrtfs. WO 01/70671 PCT/US01/09338 DETAILS OF THE INVENTION In the above recitations, the term "alkyl", used either alone or in compound words such as "alkylthio" or "haloalkyl" includes straight-chain or branched alkyl, such as, methyl, ethyl, K-propyl, z-propyl, or the different butyl, pentyl or hexyl isomers. The term "1-2 5 alkyl" indicates that one or two of the available positions for that substituent may be alkyl. "Alkenyl" includes straight-chain or branched alkenes such as 1-propenyl, 2-propenyl, and the different butenyl, pentenyl and hexenyl isomers. "Alkenyl" also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. "Alkynyl" includes straight-chain or branched alkynes such as 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl 10 isomers. "Alkynyl" can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl "Alkoxy" includes, for example, methoxy, ethoxy, rc-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers. "Alkoxyalkyl" denotes alkoxy substitution on alkyl. Examples of "alkoxyalkyl" include CH3OCH2, CH3OCH2CH2, CH3CH2OCH2, CH3CH2CH2CH2OCH2 and CH3CH2OCH2CH2. 15 "Alkylthio" includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butyltbio, pentylthio and hexylthio isomers. "Cycloalkyl" includes, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. The term^'heterocycHc ring" or heterocyclic ring system" denotes rings or ring systems in which at least one ring atom is not carbon and comprises 1 to 4 heteroatoms 20 independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that each heterocyclic ring contains no more than 4 nitrogens, no more than 2 oxygens and no more than 2 sulfurs. The heterocyclic ring can be attached through any available carbon or nitrogen by replacement of hydrogen on said carbon or nitrogen. The term "aromatic ring system" denotes fully unsaturated carbocycles and heterocycles in which the polycyclic ring 25 system is aromatic (where aromatic indicates that the Hiickel rule is satisfied for the ring system). The term "heteroaromatic ring" denotes fully aromatic rings in which at least one ring atom is not carbon and comprises 1 to 4 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that each heterocyclic ring contains no more than 4 nitrogens, no more than 2 oxygens and no more than 2 sulfurs 30 (where aromatic indicates that the Htickel rule is satisfied). The heterocyclic ring can be attached through any available carbon or nitrogen by replacement of hydrogen on said carbon or nitrogen. The term "aromatic heterocyclic ring system" includes fully aromatic heterocycles and heterocycles in which at least one ring of a polycyclic ring system is aromatic (where aromatic indicates that the Hiickel rule is satisfied). The term "fused 35 heterobicyclic ring system" includes a ring system comprised of two fused rings in which at one ring atom is not carbon and can be aromatic or non aromatic, as defined above. The term "halogen", either alone or in compound words such as "haloalkyl", includes when used in cnm-nound words such as WO 01/70671 PCT/US01/09338 "haloalkyl", said alkyl may be partially or fully substituted with halogen atoms which may be the same'or different. Examples of "haloalkyl" include F3C, CICH2, CF3CH2 and CF3CC12. The terms "haloalkenyl", "haloalkynyl", "haloalkoxy", and the like, are defined analogously to the term "haloalkyl". Examples of "haloalkenyl" include (C1)20=CHCH2 5 and CF3 CH2CH=CHCH2. Examples of "haloalkynyl" include HCsCCHCL CF3OC, CCI3OC and FCH2OCCH2. Examples of "haloalkoxy" include CF30, CC13CH20, HCF2CH2CH20 and CF3CH20. The total number of carbon atoms in a substituent group is indicated by the "Ci-Cj" prefix where i and j are numbers from 1 to 6. For example, CyC^ alkylsulfonyl designates 10 methylsulfonyl through propylsulfonyl; C2 alkoxyalkyl designates CH3OCH2; C3 alkoxyalkyl designates, for example, CH3CH(OCH3), CH3OCH2CH2 or CH3CH2OCH2; and C4 alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH3CH2CH2OCH2 and CH3CH2OCH2CH2. In the above recitations, when a compound of 15 Formula 1 contains a heterocyclic ring, all substituents are attached to this ring through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen. When a group contains a substituent which can be hydrogen, for example R3, then, when this substituent is taken as hydrogen, it is recognized that this is equivalent to said group being unsubstituted. 20 - • Compounds of this invention can exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers. One skilled in the art will appreciate that one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). Additionally, the skilled artisan knows how to 25 separate, enrich, and/or to selectively prepare said stereoisomers. Accordingly, the compounds of the invention may be present as a mixture of stereoisomers, individual stereoisomers, or as an optically active form. The present invention comprises compounds selected from Formula 1, JV-oxides and agriculturally suitable salts thereof. One skilled in the art will appreciate that not all nitrogen 30 containing heterocycles can form iV-oxides since the nitrogen requires an available lone pair for oxidation to the oxide; one skilled in the art will recognize those nitrogen containing heterocycles which can form TV-oxides. One skilled in the art will also recognize that tertiary amines can form N-oxides. Synthetic methods for the preparation of iV-oxides of heterocycles and tertiary amines are very well known by one skilled in the art including the 35 oxidation of heterocycles and tertiary amines with peroxy acids such as peracetic and ffz-chloroperbenzoic acid (MCPB A), hydrogen peroxide, alkyl hydroperoxides such as f-butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethydioxirane. These methods fnr the nrp.nnration nf W-nviHp.5 havp been extensivelv described and reviewed in the WO 01/70671 PCTAJS01/09338 literature, see for example: T. L. Gilchrist in Comprehensive Organic Synthesis, vol. 7, pp 748-750, £>. V. Ley, Ed, Pergamon Press; M. Tisler and B. Stanovnik in Comprehensive Heterocyclic Chemistry, vol. 3, pp 18-19, A. J. Boulton and A. McKiHop, Eds., Pergamon Press; M. R. Grirnmett and B. R. T. Keene in Advances in Heterocyclic Chemistry, vol. 43, 5 pp 139-151, A. R. Katritzky, Ed., Academic Press; M. Tisler and B. Stanovnik in Advances in Heterocyclic Chemistry, vol. 9, pp 285-291, A. R. Katritzky and A. J. Boulton, Eds., Academic Press; and G. W. H. Cheeseman and E. S. G. Wersriuk in Advances in Heterocyclic Chemistry, vol. 22, pp 390-392, A. R. Katritzky and A. J. Boulton, Eds.,' Academic Press. 10 The salts of the compounds of the invention include acid-addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, furnaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids. Of note are certain compounds of Formula II 15 wherein XandYareO; m is 1 to 5; n is 1 to 4; 20 R1 is H; or CrC6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or C3-C6 cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO2, hydroxy, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, CrC4 alkylsulfonyl, C2-C4 alkoxycarbonyl, C1-C4 alkylarnino, C2-Cg dialkylamino and C3-C6 cycloalkylamino; or 25 R1 is C2-Cg alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl or C3-Cg dialkylaminocarbonyl; WO 01/70671 PCT/US01/09338 R2 is H, CrC6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, CrC4 alkoxy, CrC4 aUcylamino, C2~Cg dialkylamino, C3-C alkoxycarbonyl or C2-C6 alkylcarbonyl; R3 is z-propyl or ?-butyl; and 5 each R4 and R5 are independently H, Ci~C6 alkyl, C2-Q alkenyl, C2-Cg alkynyl, C3-C6 cycloalkyl, Cj-Cg haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, CrC6 halocycloalkyl, halogen, CN, C02H, CONH2, N02, hydroxy, CrC4 alkoxy, C^-04 haloalkoxy, Cj-04 alkylthio, Q-C4 alkylsuLfinyl, Ct-C4 alkylsulfonyl, CJ-C4 haloalkylthio, Cj-C4 haloalkylsulfinyl, C1-C4 10 haloalkylsulfonyl, CrC4 alkoxycarbonyl, C1-C4 alkylamino, C2-C§ diallcylamino, C3-Cg cycloalkylamino, C2-Cg alkylcarbonyl, C2-C5 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-Cg dialkylarainocarbonyl, C3-C6 trialkylsilyl; or - ■ each R4 and R5 are independently phenyl optionally substituted with CpC4 alkyl, 15 Qrc4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, CrC4 haolalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-Cg halocycloalkyl, halogen, CN, N02, CrC4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, CrC4 alkylsulfonyl C]-C4 alkoxycarbonyl, (VC4 alkylamino, C2-C8 dialkylamino, C3-Cg cycloalkylamino, C3-C6 (alkyl)cycloalkylarnino, C2-C4 alkylcarbonyl, 20 C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-Cg dialkylaroinocarbonyl or C3-Cg trialkylsilyl. Also of note are methods for controlling arthropods comprising contacting the arthropods or their environment with an arthropodicidally effective amount of a compound of Formula II and insecticidal compositions thereof. 25 Also of note are certain compounds of Formula m wherein A and B are independently 0 or S; WO 01/70671 PCT/US01/09338 J is a phenyl group substituted with 1 to 2 R5 and optionally substituted ■with 1 to 3 R6, or a 5- or 6-membered heteroaromatic ring optionally substituted with 1 to 4 R7; n is 1 to 4; 5 R1 is H; or CrC6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or C3-C6 cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, N02, hydroxy, Cj-C4 alkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, Ci-C4 alkylsulfonyl, C2-C4 alkoxycarbonyl, C1-C4 alkylarnino, C2-Cg dialkylamino and C3-Cg cycloaU^lamino; or 10 R1 is C2-C6 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylarninocarbonyl or C3-Cg dialkylaminocarbonyl; R2 is H, CrC6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, CrC4 alkoxy, CJ-C4 alkylarnino, C2-Cg dialkylamino, C3-C6 cycloalkylamino, Qj-Cg alkoxycarbonyl or C^-Cg alkylcarbonyl; 15 R3 is H; or CrC6 alkyl, C2-C6 alkenyl, C2~C6 alkynyl or C3-C6 cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, N02, hydroxy, (VC4 alkoxy, (VC4 alkylthio, C1-C4 alkylsulfinyl and CyC^ alkylsulfonyl; or R2 and R3 can be taken together with the nitrogen to which they are attached to form 20 a ring containing 2 to 6 atoms of carbon and optionally one additional atom of nitrogen, sulfur or oxygen, said ring may be optionally substituted with 1 to 4 substituents selected from the group consisting of Ci~C2 alkyl, halogen, CN, N02 and Cj-C^ alkoxy; each R4 is independently H, Cj-Cg, alkyl, C2-C5 alkenyl, C2-Cg alkynyl, C3-Cg 25 cycloalkyl, CrC6 haloalkyl, C^-Cg haloalkenyl, C2-C6 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, C02H, CONH2,N02, hydroxy, CrC4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, Cj-C4 alkylsulfinyl, C^-C4 alkylsulfonyl, C!-C4 haloalkylthio, C!-C4 haloalkylsulfinyl, C!-C4 haloalkylsulfonyl, CrC4 alkylarnino, C2-C8 dialkylamino, C3-C6 cycloallcylamino, C2-C6 alkylcarbonyl, 30 C2-Cg alkoxycarbonyl, C2-Cg alkylarninocarbonyl, C3-Cg dialkylaminocarbonyl, C3-C6 trialkylsilyl; or each R4 is independently phenyl, benzyl or phenoxy, each optionally substituted with CrC4 alkyl, CrC4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, CrC4 haolalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, 35 N02, CJ-C4 alkoxy, CrC4haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, C!-C4 alkylsulfonyl, C1-C4 alkylarnino, C2-Cg dialkylamino, C3-C6 cycloalkylamino, C3-C6 (alkyl)cycloalky]amrno, C2-C4 alkylcarbonyl, C^-Cg WO 01/70671 PCT/US01/09338 alkoxycarbonyl, Cj-C^ alkylaminocarbonyl, C3-Cg diallcylaminocarbonyl or C3-C6 trialkylsilyl; each R5 is independently Cj-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-Cg halocycloalkyl, CrC4 haloalkoxy, CrC4 alkyltbio, CrC4 alkylsulfinyl, 5 crc4 alkylsulfonyl, CrC4 haloalkylthio, CrC4 haloalkylsulfinyl.. CrC4 haloalkylsnlfonyl, CN, N02, CrC4 alkylamino, C2-Cs dialkylamino, C3-C6 cycloalkylamino, C2-Cg alkylcarbonyl, C2-C6 alkoxycarbonyl, C^-Cg alkylaminocarbonyl, or C3-Cg dialkylaminocarbonyl; or (R5)2 when attached to adjacent carbon atoms can be taken together as -OCF20-, 10 -CF2CF20-5 or -OCF2CF20-; each R6 is independently H, halogen, CpCg alkyl, C2-C6 alkenyl, C2-Cs alkynyl, C3- Cg cycloalkyl, Ci~C4 alkoxy; or - each R6 is independently phenyl, benzyl or phenoxy, each optionally substituted with CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, CrC4 haolalkyl, 15 C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, N02, CrC4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, Cr C4 alkylsulfonyl, Cj-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C3-Cg (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alfylaminocarbonyl, C3-C8 dialkylaminocarbonyl or C3- 20 C6 trialkylsilyl; each R7 is independently H, Cj-C6 alkyl, Cj-Cg alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, CrC6 haloalkyl, C2-Cg haloalkenyl, C2-C6 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, C02H, CONH2, N02, hydroxy, CrC4 alkoxy, Cj-04 haloalkoxy, Cj-C4 alkylthio, Cj-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, 25 CrC4 haloalkylthio, CrC4 haloalkylsulfinyl, CrC4 haloalkylsulfonyl, CrC4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkylcarbonyl, C2-Cg alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl, C3-Cg trialkylsilyl; or each R? is independently phenyl, benzyl or phenoxy, each optionally substituted with 30 CrC4 alkyl, C2-C4 alkenyl, CrC4 alkynyl, C3-C6 cycloalkyl, CrC4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-Cg halocycloalkyl, halogen, CN, N02, CrC4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, Cr C4 alkylsulfonyl Cj^ alkoxycarbonyl, C}-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C3-C6 (alkyl)cycloallqrtamino, C2-C4 alkylcarbonyl, 35 C2-Cg alkoxycarbonyl, C2-Cg alkylaminocarbonyl, C3-C3 dialkylaminocarbonyl or C3-Cg trialkylsilyl. WO 01/70671 PCT/US01/09338 Also of note are methods for controlling arthropods comprising contacting the arthropods or their environment with an arthropodicidally effective amount of a compound of Formula IE and insecticidal compositions thereof. Also of note are certain compounds of Formula IV 5 wherein A and B are independently O or S; J is a phenyl group substituted with 1 to 2 R5, and optionally substituted with 1 to 3 R6, or a 5- or 6-membered heteroaromatic ring optionally substituted with 1 to 4 10 R7; n is 1 to 4; R1 is H; or CVCs alkyl, C2-Cg alkenyl, C2-C6 alkynyl or C3-C6 cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, N02, hydroxy, C1-C4 alkoxy, C1-C4 alkylthio, Q-C4 15 alkylsulfinyl, C1-C4 alkylsulfonyl, Q2-C4 alkoxycarbonyl, C1-C4 alkylamino, C2-Cg a^alkylarnino and C3-C6 cycloalkylamino; or R1 is C2-Cg alkylcarbonyl, C^-Cg alkoxycarbonyl, C2-Cg alkylaminocarbonyl or C3-Cg dialkylaminocarbonyl; R2 is H, CrC6 alkyl, C2-C6 alkenyl, CrC6 alkynyl, C3-C6 cycloalkyl, CrC4 alkoxy, 20 C1-C4 alkylamino, C2-Cg dialkylamino, CyCg cycloaU^lamino, C2-C6 alkoxycarbonyl or C2-Cg alkylcarbonyl; R3 is H; CrC6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, N02, hydroxy, CVC4 alkoxy, C1-C4 alkylthio, C1-C4 25 alkylsulfinyl and C1-C4 alkylsulfonyl; C1-C4 alkoxy; Ci-C4'alkylamino; C2-Cg dialkylamino; C3-C6 cycloalkylamino; C2-Cg alkoxycarbonyl or C2-Cg alkylcarbonyl; or R2 and R3 can be taken together with the nitrogen to which they are attached to form a ring containing 2 to 6 atoms of carbon and optionally one additional atom of 30 nitrogen sulfur r\r nwop.n said ring may be optionally substituted with 1 to 4 WO 01/70671 PCT7US01/09338 substituents selected from the group consisting of C1-C2 alkyl, halogen, CN, NO2 and C1-C2 alkoxy; each R4 is independently H, CrC6 alkyl, C^-Cg alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, CpCg haloalkyl, C2-C6 haloalkenyl, C2-Cg haloalkynyl, C3-C6 5 halocycloalkyl, halogen, CN, C02H, CONH2, N02, hydroxy, CrC4 alkoxy, CrC4 haloalkoxy, C1-C4 alkylthio, C]^ alkylsulfinyl, CrC4 alkylsulfonyl, CrC4 haloalkylthio, CrC4haloalkylsulfinyl, C1-C4haloalkylsulfonyl, Cj-Q alkylarnino, C2-C8 dialkylamino, C3-Cg cycloalkylamino, C2-C6 alkylcarbonyl, C2-Cg alkoxycarbonyl, C2-Cg alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl, 10 C3-Ce trialkylsilyl; or each R4 is independently phenyl, benzyl or phenoxy, each optionally substituted with CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, CrC4 haolalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, N02, Cj-C4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, Cr 15 C4 alkylsulfonyl, Ci-C4 alkylarnino, C2-Cs dialkylamino, C3-Cg cycloalkylarniiio, C3-Cg (allcyl)cycloalkylarrihio, C2-C4 alkylcarbonyl, C2-Cg , alkoxycarbonyl, C2-Cg altylaminocarbonyl, C3-C8 dialkylaminocarbonyl or C3-C6 trialkylsilyl; each R5 is independently Cj-Cg alkyl, Q2-C6 alkenyl C2-Cg alkynyl, C3-Cg 20 cycloalkyl, CrC6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, C02H, CONH2, N02, hydroxy, CrC4 alkoxy, CyC^ haloalkoxy, CrC4 alkylthio, CX-C4 alkylsulfinyl, Cj-C4 alkylsulfonyl, Ci-C4 haloalkylthio, CrC4 haloalkylsulfinyl, C2-C4 haloalkylsulfonyl, Ci-C4 alkylarnino, C2-C8 dialkylarnino, C3-Cg cycloalkylamino, GrCg alkylcarbonyl, 25 C2-Cg alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8 diaHcylarninocarbonyl, C3-Cg trialkylsilyl; or (R5)2 when attached to adjacent carbon atoms can be taken together as -0CF2O, -CF2CF20-r or-OCF2CF20-; each R6 is independently H, halogen, Cj-Cg alkyl, C2-Cg alkenyl, C2-C6 alkynyl, C3- 30 C6 cycloalkyl, C1-C4 alkoxy; or each R6 is independently a phenyl, benzyl, phenoxy or a 5- or 6-membered heteroaromatic ring, each ring optionally substituted with C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-Cg cycloalkyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, N02, Ci-C4 alkoxy, Cr 35 C4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, CrC4 alkylsulfonyl, CrC4 alkylarnino, C2-Cg dialkylamino, C3-Cg cycloall^lamino, C3-Cg (alkyl)cycloalkylamino, Q2-C4 alkylcarbonyl, C^Cg alkoxycarbonyl, C2-Cg niVviflTTiJinnr^rKnnvi n^n„ /«aii^iarninocarbonvl or Ci-C* trialkvlsilvl: WO 01/70671 PCT/US01/09338 each R7 is independently H, C1-C6 alkyl, C2-Cg alkenyl, C2-Cg alkynyl, C3-C6 cycloalkyl, Cj-Cg haloalkyl, C2-Cg haloalkenyl C2-Cg haloalkynyl, C3-Cg halocycloalkyLhaiogen, CN, C02H, CONH2, N02, hydroxy, CrC4 alkoxy, Cj-C4 haloalkoxy, CrC4 alkylthio, C^-Q alkylsulfinyl, C1-C4 alkylsulfonyl, 5 crc4 haloalkylthio, CrC4 haloalkylsulfinyl, CrC4 haloalkylsulfonyl, Cx-C^. aLkylamhio, C2-C8 dialkylamino, C3-Cg cycloalkylamino, C2-Cg alkylcarbonyl, C2-Cg alkoxycarbonyl, C2-Cg alkylarninocarbonyl, C3-C8 dialkylaminocarbonyl., C3-C6 trialkylsilyl; or each R7 is independently a phenyl, benzyl, benzoyl, phenoxy or a 5- or 6-membered 10 heteroaromatic ring, each ring optionally substituted with C]-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, Cj-C4 haolalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, N02, C!-C4 alkoxy, Cr C4 haloalkoxy, Ci-C4 alkylthio, C1-C4 alkylsulfinyl, Ci-C4 alkylsulfonyl, CrC4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C3-Cg 15 (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C^-Cg alkoxycarbonyl, C2-Cg alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl or C3-Cg trialk>rlsilyl; provided that when A and B are both 0, R2 is H or C]_-C3 alkyl, R3 is H or C\|-C3 alkyl and R4 is H, halogen, CrC6 alkyl, phenyl, hydroxy or Ci-C6 alkoxy, then one R5 is other than halogen, C^Cg alkyl, hydroxy or Cj-Cg alkoxy. 20 Also of note are methods for controlling arthropods comprising contacting the arthropods or their environment with an arthropodicidally effective amount of a compound of Formula IV and insecticidal compositions thereof. Preferred methods for reasons of better activity are: Preferred 1. Methods comprising compounds of Formula 1 wherein J is a phenyl 25 group substituted with 1 to 2 R5 and optionally substituted with 1 to 3 R6. Preferred 2. Methods of Preferred 1 wherein A and B are both O; n is 1 to 2; R1 is H, CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, CrC6 cycloalkyl, C2-C6 30 alkylcarbonyl or C2-C6 alkoxycarbonyl; R2 is H, CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C2-C6 alkylcarbonyl or C2-Cg alkoxycarbonyl; R3 is Cj-Cg alkyl, Qj-Cg alkenyl, C2-Cg alkynyl or C3-C6 cycloalkyl each optionally substituted with one or more substituents selected from the group 35 consisting of halogen, CN, Cj^ alkoxy, Cj-C^ alkylthio, C^^ alkylsulfinyl and Ci-C2 alkylsulfonyl; one of the R4 groups is attached to the phenyl ring at the 2-position or 5-position, and said T?4 is C.,-r. WO 01/70671 PCT/US01/09338 alkoxy, CyC^. haloalkoxy, CyC^ alkylthio, C1-C4 alkylsulfinyl, CyC4 alkylsulfonyl, CyC$ haloalkylthio, CyC^ haloalkylsulfinyl or C1-C4 haloalkylsulfonyl; each R5 is independently C1-C4 haloalkyl, GN, N02, CrC4 haloalkoxy, C}-^ 5 alkylthio, CrC4 alkylsulfinyl, CrC4 alkylsulfonyl, CrC4 haloalkylthio, CrC4 haloalkylsulfinyl, CrC4 haloalkylsulfonyl or C2- C4 alkoxycarbonyl; or (R5)2 when attached to adjacent carbon atoms can be taken together as -OCF20-, -CF2CF20- or -OCF2CF20-; and 10 each R6 is independently H, halogen, CrC4 alkyl, CrC2 alkoxy or C?-C4 alkoxycarbonyl, or each R6 is independently a phenyl or a 5- or 6-membered heteroaromatic ring, each ring optionally substituted with CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3~C6 cycloalkyl, CrC4 haloalkyl, C2-C4 haloalkenyl, C2~C4 15 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN,N02, CrC4 alkoxy, C2-C4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, CrCA alkylsulfonyl, CyC4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C3-C6 (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8 20 dialkylaminocarbonyl or C3-C6 trialkylsilyl. Preferred 3. Methods of Preferred 2 wherein R1 and R2 are both H; R3 is CrC4 alkyl optionally substituted with halogen, CN, OCH3, S(0)pCH3; each R4 is independently H, CH3, CF3i OCF3, OCHF2, S(0)pCF3, S(0)pCHF2, CN 25 or halogen; eachR5 is independently CF3, OCF3> OCHF2, S(0)pCF3, S(0)pCHF2, OCH2CF3, OCF2CHF2, S(0)pCH2CF3 or S(0)pCF2CHF2; each R6 is independently H, halogen or methyl; or phenyl, pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted with 30 CrC4 alkyl, CrC4 haloalkyl, halogen or CN; and p is 0,1 or 2. Preferred 4. Methods of Preferred 3 wherein R3 is z-propyl or f-butyl. Preferred 5. Methods comprising compounds of Formula 1 wherein J is a 5- or 6- membered heteroaromatic ring optionally substituted with 1 to 4 R7. 35 Preferred 6. Methods of Preferred 5 wherein J is a 5- or 6-membered heteroaromatic ring selected from the group consisting of J-1, J-2, J-3, J-4 and J-5, each J optionally substituted with 1 to 3 R7 WO 01/70671 PCT/US01/09338 QisO, SorNR7;and W, X, Y and Z axe independently N or CR7, provided that in J-4 and J-5 at least one of W, X, Y or Z is N. 5 Preferred 7. Methods of Preferred 5 or Preferred 6 wherein A and B are O; n is 1 to 2; R1 is H, CrC4 alkyL C2-C4 alkenyl, C2-C4 alkynyl, C2-C6 alkylcarbonyl or C2-Cg alkoxycarbonyl; 10 R2 is H, CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C2-C6 alkylcarbonyl or C^-Cg alkoxycarbonyl; R3 is H; or C^Cg alkyl, C2-C6 alkenyl, C2-C6 alkynyl or C3-C6 cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, C^-C^ alkoxy, C1-C2 alkylthio, 15 . CrG2 alkylsulfinyl and CrC2 alkylsulfonyl; one of the R4 groups is attached to the phenyl ring at the 2-position, and said R4 is CrC4 alkyl, CrC4 haloalkyl, halogen, CN, N02, C x -C4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, CVC4 alkylsulfonyl, CrC4 haloalkylthio, C}^ haloalkylsulfinyl, or C1-C4 20 haloalkylsulfonyl; and each R7 is independently H, Cj-C4 alkyl, C2-C4 haloalkyl, halogen, CN, N02, CrC4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, CrC4 alkylsulfonyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, Ci-C4 haloalkylsulfonyl or C2-C4 alkoxycarbonyl; or a phenyl or a 5- or 25 6-membered heteroaromatic ring, each ring optionally substituted with CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl C3-C6 cycloalkyl, CrC4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-Cg halocycloalkyl, halogen, CN, N(>2, Ci~C4 alkoxy, Cj-C4 haloalkoxy, CrC4 alkylthio, r.-r. niwi«iifiTwi r._c4 alkvlsulfonvL Ci-C alkvlarnino. C-C» WO 01/70671 PCT/USQ1/09338 cUalkylamino, C3-C6 cycloalkylamino, C3-C6 (alkyl)cycloaIkylamino, C2-C4 atkylcarbonyl, ^-Cg alkoxycarbonyl, C^-Cs alkylaininocarbonyl, C3-Cg dialkylaminocarbonyl or C3-C6 trialkylsilyl. Preferred 8. Methods of Preferred 7 wherein 5 J is selected from the group consisting of pyridine, pyrirnidine, pyrazole, imidazole, triazole, thiophene, tbiazole and oxazole, furan, isothiazole and isoxazole, each optionally substituted with 1 to 3 R7. Preferred 9. Methods of Preferred 8 wherein J is selected from the group consisting of pyridine, pyrirnidine, pyrazole, 10 thiophene and thiazole, each optionally substituted with 1 to 3 R7; R1 and R2 are both H; R3 is CrC4 alkyl optionally substituted with halogen, CN, OCH3, S(0)pCH3; each R4 is independently H, CH3, CF3, OCF3, OCHF2, S(0)pCF3, S(0)pCHF2, CN or halogen; 15 each R7 is independently H, halogen, CH3, CF3, OCHF2, S(0)pCF3, S(0)pCHF25 OCH2CF3, OCF2CHF2, S(0)pCH2CF3, S(0)pCF2CHF2; or phenyl, pyrazole, imidazole, triazole, pyridine or pyrirnidine, each ring optionally substituted with CVC4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio, C1-C4 alkylsulfinyl, CrC4 20 alkylsulfonyl, halogen or CN; and p is 0,1 or 2. Preferred 10. Methods of Preferred 9 wherein J is a pyridine optionally substituted with 1 to 3 R7. Preferred 11. Methods of Preferred 10 wherein one R7 is a phenyl optionally substituted 25 with CrC4 alkyl, CrC4 haloalkyl, halogen or CN. Preferred 12. Methods of Preferred 10 wherein one R7 is a pyrazole, imidazole, triazole, pyridine or pyrirnidine, each ring optionally substituted with Cj-C4 alkyl, C1-C4 haloalkyl, halogen or CN. Preferred 13. Methods of Preferred 9 wherein J is a pyrirnidine optionally substituted 30 with 1 to 3 R7. Preferred 14. Methods of Preferred 13 wherein one R7 is a phenyl optionally substituted with C!-C4 alkyl, C1-C4 haloalkyl, halogen or CN. Preferred 15. Methods of Preferred 13 wherein one R7 is a pyrazole, imidazole, triazole, pyridine or pyrirnidine, each ring optionally substituted with C1-C4 alkyl, C1-C4 35 haloalkyl, halogen or CN. Preferred 16. Methods of Preferred 9 wherein J is a pyrazole optionally substituted with 1 to 3 R7. WO 01/70671 PCT/US01/09338 Preferred 17. Methods of Preferred 16 wherein one R7 is a phenyl optionally substituted with Ci-C4 alkyl, CrC4 haloalkyl, halogen or CN. Preferred 18. Methods of Preferred 16 wherein one R7 is a pyrazole, imidazole, triazole, pyridine or pyrirnidine, each ring optionally substituted with CVC4 alkyl, CrC4 5 haloalkyl, halogen or CN. Preferred 19. Methods of Preferred 18 wherein R7 is a pyridine optionally substituted with C] -C4 alkyl, Cj -C4 haloalkyl, halogen or CN. Most preferred is the method comprising a compound of Formula 1 selected from the group consisting of: 10 3-methyl-iV-(l -me&ylethyl)-2-[[4-(trifluorome 2-memyl-A^-[2-memyl-6-[[(l-memylemyl)amino]carbonyl]phenyl]-4-(trifluoromethyl)benzamide, 2-me1hyl-iV-[2-memyl-6-[[(l-memylemyl)anuno]carbonyl]phenyl]-6- (trifluoromemyl)-3-pyridinecarboxamide, 15 1 -ethyl-JV-[2-methyl-6-[[(l -memylemyl)arnino]carbonyl]phenyl]-3- (trifluoromethyl)- li7-pyrazole-5-carboxamide, l-(2-fluorophenyl)-iV-[2-memyl^-[[(l-memylemyl)amino)carbonyl]phenyl]-3- (trifluoromethyl)-l^f-pyrazoler5-carboxarnide, l-(3^hloro-2-pyria^yl)-iV'-[2-memyl-64^ 20 (trifluoromethyl)- lif-pyra2ole-5-carboxamide, JN^[2-cmoro-6-[[(l-memylemyl)arrdno]carbonyl]phenyl]-l-(3-chloro-2-pyridinyl)-3-- (trifluoromemyl)-liif-pyrazole-5-carboxamide, 5-bromo-l-(2-chlorophenyl)-A'-[2-methyl-6-[[(l- memylemyl)amino]carbonyl]phenyl]- l^T-pyrazole-5-carboxamide, and 25 3-bromo-iV'-[2-cWoro-6-[[(l-memylemyl)aminoJcarbonyl]phenyl]-l-(2- cMorophenyl)-li?-pyrazole-5-carboxamide. Preferred compounds for reasons of better activity and/or ease of synthesis are: Preferred A. Compounds of Formula 1 wherein J is a phenyl group substituted with 1 to 2 R5 and optionally substituted with 1 to 3 R6.. 30 Preferred B. Compounds of Preferred A wherein A and B are both 0; n is 1 to 2; Rl is H, CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C2-C6 . alkylcarbonyl or C2-C6 alkoxycarbonyl; 35 R2 is H, CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C2-C6 alkylcarbonyl or C^-Cg alkoxycarbonyl; R3 is CrC6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or C3-C6 cycloalkyl each with one or more substituents selected from the WO 01/70671 PCT/US01/09338 group consisting of halogen, CN, C1-C2 alkoxy, C1-C2 alkylthio, Ci~C2 alkylsulfinyl and C1-C2 alkylsulfonyl; one of the R4 groups is attached to the phenyl ring at the 2-position. or 5- position, and said R4 is C1-C4 alkyl, C1-C4 haloalkyl, halogen, CN, 5 N02, C!-C4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, C1-C4 alkylsulfonyl, CrC4 haloalkylthio, CrC4 haloalkylsulfinyl or C!-C4 haloalkylsulfonyl; each R5 is independently C1-C4 haloalkyl, CN, NO2, C1-C4 haloalkoxy, Cr C4 alkylthio, CrC4 alkylsulfinyl, C]-C4 alkylsulfonyl, CrC4 10 haloalkylthio, C1-C4 haloalkylsulfinyl, CrC4 haloalkylsulfonyl or C2~ C4 alkoxycarbonyl; or (R5)2 when attached to adjacent carbon atoms can be taken together as - OCF20-, -CF2CF20- or.-OCF2CF20-; and each R6 is independently H, halogen, CrC4 alkyl, CrC2 alkoxy or C2-C4 15 alkoxycarbonyl, or each R6 is independently a phenyl or a 5- or 6-membered heteroaromatic ring, each ring optionally substituted with CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, N02, CrC4 alkoxy, 20 C1-C4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, CrG4 alkylsulfonyl, CrC4 alkylarnino, C2-Cg dialkylamino, C3-Cg cycloalkylamino, C3-C6 (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-Cg alkylaminocarbonyl, C3-C8 dialkylarninocarbonyl or C3-C6 trialkylsilyl. 25 Preferred C. Compounds of Preferred B wherein R1 and R2 are both H; R3 is CrC4 alkyl optionally substituted with halogen, CN, OCH3, S(0)pCH3; each R4 is independently H, CH3, CF3, OCF3, OCHF2, S(0)pCF3, S(0)pCHF2, CN or halogen; 30 each R5 is independently CF3, OCF3, OCHF2, S(0)pCF3, S(0)pCHF2, OCH2CF3, OCF2CHF2, S(0)pCH2CF3 or S(0)pCF2CHF2; each R6 is independently EL halogen or methyl; or phenyl, pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted with Cj-Q alkyl, CrC4 haloalkyl, halogen or CN; and 35 p is 0,1 or 2. Preferred D. Compounds of Preferred C wherein R3 is i-propyl or f-butyl. Preferred E. Compounds of Formula 1 wherein J is a 5- or 6-membered heteroaromatic rinff ontionallv substituted -with 1 to 4 R7. WO 01/70671 PCT/US01/09338 Preferred F. Compounds of Preferred E wherein J is a 5- or 6-membered heteroaromatic ring selected from the group consisting of J-l, J-2, J-3, J-4 and J-5, each J optionally substituted with 1 to 3 R7 5 Q is 0, S or NR7; and W, X, Y and Z are independently N or CR7, provided that in J-4 and J-5 at least one of W, X, Y or Z is N. Preferred G. Compounds of Preferred E or Preferred F wherein 10 AandBareO; n is 1 to 2; R1 is H, CrC4 alkyl, CrC4 alkenyl, C2-C4 alkynyl, C2-C6 alkylcarbonyl or C^-Cg alkoxycarbonyl; R2 is H, CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C2-C6 15 alkylcarbonyl or C2~C6 alkoxycarbonyl; R3 is H; or CrC6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or C3-C6 cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, C1-C2 alkoxy, Ci~C2 alkylthio, C!-C2 alkylsulfinyl and Ci~C2 alkylsulfonyl; 20 one of the R4 groups is attached to the phenyl ring at the 2-position, and said R4 is CrC4 allcyl, CrC4 haloalkyl, halogen, CN, N02, CrC4 alkoxy, CrC4 haloalkoxy, C^Q^ alkylthio, CrC4 alkylsulfinyl, Ci~C4 alkylsulfonyl, CrC4 haloalkylthio, CrC4 haloalkylsurfirryl or Ci-Q haloalkylsulfonyl; and 25 each R7 is independently H, Ci~C4 alkyl, C1 -C4.haloalkyl, halogen, CN, N02, CrC4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, CrC4 alkylsulfonyl, Ci-C4 haloalkylthio, CrC4 haloalkylsulfiriyl, Cj-Cj haloalkylsulfonyl or C2-C4 alkoxycarbonyl; or a phenyl or a 5- or WO 01/70671 PCT/US01/09338 6-membered heteroaromatic ring, each ring optionally substituted with CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, CrC4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, N02, CrC4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio, 5 CrC4 alkylsulfinyl, Cj-Q alkylsulfonyl, CrC4 alkylamino, C^-Cg dialkylamino, C3-C6 cycloalkylamino, C3-C6 (alkyl)cycloa!kylamino, C2-C4 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl or C3-C£ trialkylsilyl. Preferred H. Compounds of Preferred G wherein 10 J is selected from the group consisting of pyridine, pyrirnidine, pyrazole, imidazole, triazole, thiophene, thiazole and oxazole, furan, isothiazole and isoxazole, each optionally substituted with 1 to 3 R7. Preferred I. Compounds of Preferred H.wherein J is selected from the group consisting of pyridine, pyrirnidine,. pyrazole, 15 thiophene and thiazole, each optionally substituted with 1 to 3 R7; R1 and R2 are both H; R3 is CrC4 alkyl optionally substituted with halogen, CN, OCH3, S(0)pCH3; each R4 is independently H, CH3, CF3, OCF3, OCHF2, S(0)pCF3, S(0)pCHF2, CN or halogen; 20- each R7 is independently H, halogen, CH3, CF3, OCHF2, S(0)pCF3, S(0)pCHF2s OCH2CF3, OCF2CHF2, S(0)pCH2CF3, S(0)pCF2CHF2; or phenyl, pyrazole, imidazole, triazole, pyridine or pyrirnidine, each ring optionally substituted with C1-C4 alkyl, Cj-Q haloalkyl, Cj-C4 alkoxy, C^Q^ haloalkoxy, CrC4 alkylthio, C!-C4 alkylsulfinyl, Ci-C4 25 alkylsulfonyl, halogen or CN; and p is 0,1 or 2. Preferred J. Compounds ofPreferred I wherein J is a pyridine optionally substituted with 1 to 3 R7. Preferred K. Compounds ofPreferred J wherein one R7 is a phenyl optionally 30 substituted with C^C^ alkyl, C^C^. haloalkyl, halogen or CN. Preferred L. Compounds ofPreferred J wherein one R7 is a pyrazole, imidazole, triazole, pyridine or pyrirnidine, each ring optionally substituted with Ci~C4 alkyl, C^Q haloalkyl, halogen or CN. Preferred M. Compounds ofPreferred I wherein J is a pyrirnidine optionally substituted 35 withlto3R7. Preferred N. Compounds of Preferred M wherein one R7 is a phenyl optionally substituted with Cj-Q^ alkyl, Ci-C4 haloalkyl, halogen or CN. WO 01/70671 PCT/US01/09338 Preferred 0. Compounds of Preferred M wherein one R7 is a p'yrazole, imidazole, triazole, pyridine or pyrrolidine, each ring optionally substituted with CrC4 alkyl, C1-C4 haloalkyl, halogen or CN. Preferred P. Compounds of Preferred I wherein J is a pyrazole optionally substituted 5 with 1 to 3 R7. Preferred Q. Compounds of Preferred P wherein one R7 is a phenyl optionally substituted with CyC^ alkyl, CrC4 haloalkyl, halogen or CN. Preferred R Compounds ofPreferredP wherein one R7 is a pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted with CrC4 10 alkyl, CrC4 haloalkyl, halogen or CN. Preferred S. Compounds of Preferred R wherein R7 is a pyridine optionally substituted with Cj-C4 alkyl, CrC4 haloalkyl, halogen or CN. Most preferred is the"\|6mpound of Formula 1 selected from the group consisting of: 3-memyl-iV'-(l-memylethyl)-2-[[4-(trifluoromethyl)benzoyl]amm 15 2-methyl-iV-[2-methyl-6-[[(l -methylethyl)amino]carbonyl]phenyI]-4- (trifiuoromethyl)benzamide, 2-methyl-iVr-[2-methyl-6-[[(l-methylemyl)ammoJcarbonyI]phenyl]-6-(trifluoromethyl)-3-pyridme(^rboxainide, l-ethyl-i^P-memyl^-fKl-methylemylJarnmolcarbonyllphenylJ-S- 20 (trifmoromethyl)- lH-pyrazole-5-carboxamide, l-(2-fluorophenyl)-iV'-[2-methyl-6-[[(l-memylethyl)annno)carbonyl]phenyl]-3-(trifluoromethyl)-liT-pyrazole-5-carboxamide, l-(3-cmoro-2-pyridmyl)-A^-[2-memyl-6-[[(l-memylemyl)ammo]carbonyl]phen^ (trifluoromethyl)-lF-pyrazole-5-carboxamide, 25 JV"-[2 (trifluoromethyl)-l-H'-pyrazole-5-carboxamide, i-bromo-l-(2-chlorophenyl)-JV-[2-methyl-6-[[(l- methyleihyl)arnmo3carbonyl]phenyl3-lif-pyrazole-5-carboxamide,and 3-bromo-iy"-[2-cUoro-6-[[(l-methylemyl)amino]carbonyl]phenyl]-l-(2- 30 cHorophenyI)-l#-pyrazoIe-5-carboxamide. Preferred compositions are those comprising compounds of formula 1 as preferred in Preferred 1 through 19, and the specifically preferred compounds above. As noted above, each J is independently a phenyl group or a naphthyl group substituted with 1 to 2 R5 and optionally substituted with 1 to 3 R6; or each J is 35 independently a 5- or 6-membered heteroaroinatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system wherein each ring or ring system is optionally substituted with 1 to 4 R7. The term "optionally substituted" in connection with these J groups refers to groups which are unsubstituted or have at least one non-hydrogen substituent that does not WO 01/70671 PCT/US01/09338 extinguish the arthropodicidal activity possessed by the unsubstituted analog. Note also that J-l through J-5 above denote 5- or 6-membered heteroaromatic rings. An example of phenyl substituted with 1 to 2 R5 and optionally substituted with 1 to 3 R6 is tiie ring illustrated as J-6 in Exhibit 1, wherein m is an integer from 1 -2 and q is an integer from 1 to 3. Note that 5 at least one R5 must be present in J-6. Although R6 groups are shown in the structure J-6, it is noted that they do not need to be present since they are optional substituents. An example of a naphthyl group substituted with 1 to 2 R5 and optionally substituted with 1 to 3 R6 is J-59 illustrated in Exhibit 1, wherein m is an integer from 1-2 and q is an integer from 1 to 3. Note that at least one R5 must be present in J-59. Although R6 groups are shown in the 10 structure J-59, it is noted that they do not need to be present since they are optional substituents. Examples of 5- or 6-membered heteroaromatic ring optionally substituted with 1 to 4 R7 include the rings J-7 through J-5 8 illustrated in Exhibit 1 wherein r is an integer from 1 to 4. Note that J-7 through J-26 are examples of J-l, J-27 through J-41 are examples of J-2, J-42 through J-44 are examples of J-3, J-46 through J-53 are examples of J-4 and J-54 15 through J-58 are examples of J-5. The nitrogen atoms that require substitution to fill their valence are substituted with R7. Note that some J groups can only be substituted with less than 4 R7 groups (e.g. J-19, J-20, J-23 through J-26 and J-3 7 through J-40 can only be substituted with one R7). Examples of aromatic 8-, 9- or 10-membered fused heterobicyclic ring systems optionally substituted with 1 to 4 R7 include J-60 through J-90 illustrated in 20 Exhibit 1 wherein r is an integer from 1 to 4. Although R7 groups are shown in the structures J-7 through J-58 and J-60 through J-90, it is noted that they do not need to be present since they are optional substituents. Note that when R5, R6 and/or R7 are H when attached to an atom, this is the same as if said atom is unsubstituted. Note that when the attachment point between (R5)m, (R6)q or (R7)r and the J group is illustrated as floating, 25 (R5)m, (R6)q or (R7)r can De attached to any available carbon atom of the J group. Note that when the attachment point on the J group is illustrated as floating, the J group can be attached to the remainder of Formula 1 through any available carbon of the J group by replacement of a hydrogen atom. VWO 01/70671PCIYUS01/09338 As noted above, G is a 5- or 6-membered nonaromatic carbocyclic or heterocyclic ring, optionally including one or two ring members selected from the group consisting of C(=0), SO or S(0)2 and optionally substituted with 1 to 4 substituents selected from the 5 group consisting of C^-Cj alkyl, halogen, CN, N02 and CrC2 alkoxy. The term "optionally substituted" in connection with these G groups refers to groups which are unsubstituted or have at least one non-hydrogen substituent that does not extinguish the arthropodicidal activity possessed by the unsubstituted analog. Note that when the attachment point on the G group is illustrated as floating, the G group can be attached to the remainder of Formula 1 10 through any available carbon of the G group by replacement of a hydrogen atom. The optional substituents can be attached to any available carbon by replacing a hydrogen atom. Examples of 5- or 6-membered nonaromatic carbocyclic rings as G include the rings illustrated as G-l through G-8 of Exhibit 2, wherein such rings are optionally substituted with 1 to 4 substituents selected from the group consisting of C^-C^ alkyl, halogen, CN, N02 15 and CyC2 alkoxy. Examples of 5- or 6-membered nonaromatic heterocyclic rings as G include the rings illustrated as G-9 through G-48 of Exhibit 2, wherein such rings are optionally substituted with 1 to 4 substituents selected from the group consisting of C^^ alkyl, halogen, CN, N02 and C^-C^ alkoxy. Note that when G comprises a ring selected from G-31 through G-34, G-37 and G-38, Q1 is selected from O, S or N. Note that when G 20 is G-ll, G13, G-14, G16, G-23, G-24, G-30 through G-34, G-37 and G-38 and Q1 isN, the nitrogen atom can complete its valence by substitution with either H or CJ-C2, alkyl. 7 WO 01/70671 PCT/US01/09338 ^ As noted above, each R6 and each R7 can be independently (among others) 5- or 6- membered heteroaromatic rings or aromatic 8-, 9- or 10-membered fused heterobicyclic ring systems, each ring optionally substituted with one to three substituents independently selected from tbe group consisting of CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 5 cycloalkyl, CrC4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, N02, CrC4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, CrC4 aUkylsulfonyl, Cx-Q alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C3-C6 (allcyl)cycloalkylaniino, C2-C4 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl or C3-Cg trialkylsilyl. Examples of such 10 R6 and R7 groups include the rings or ring systems illustrated as rings J-7 through J-58 and J-60 through J-90 illustrated in Exhibit 1, except that such rings are optionally substituted with 1 to 3 substituents selected from the group consisting of CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, CrC4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, CrC6 halocycloalkyl, halogen, CN, N02, Ci~C4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio, 15 CrC4 alkylsulflnyl, CrC4 alkylsulfonyl, CrC4 alkylamino, Cj-Cg dialkylarnino, C3-C6 cycloalkylamino, C3-C6 (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-Cg alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl or C3-C6 trialkylsilyl rather than (R7)r Note that these substituents can be attached to any available carbon atom of the J group by replacement of a hydrogen atom. Note mat when the 20 attachment point on the J group is illustrated as floating, the J group can be attached to the remainder of Formula 1 through any available carbon of the J group by replacement of a hydrogen atom. One or more of the following methods and variations as described in Schemes 1-17 can be used to prepare the compounds of Formula 1. The definitions of A, B, J, R1, R2, R3, 25 R4, R5, R6, R7, m and n in the compounds of Formulae 1-34 below are as defined above in the Summary of the Invention. Compounds of Formulae la-c, 2a-b, 4a-g, 5a-b are various subsets of the compounds of Formula 1,2,4 and 5. Compounds of Formula 1 can be prepared by procedures outlined in Schemes 1-17. A typical procedure is detailed in Scheme 1 and involves coupling of an anthranilic amide of . 30 Formula 2 with an acid chloride of Formula 3 in the presence of an acid scavenger to provide the compound of Formula la. Typical acid scavengers include amine bases such as triethylarnine, diisopropylemylarnine and pyridine; other scavengers include hydroxides such as sodium and potassium hydroxide and carbonates such as sodium carbonate and potassium carbonate. In certain instances it is useful to use polymer-supported acid scavengers such as 35 polymer-bound diisopropylemylarnine and polymer-bound dimethylammopyridine. In a subsequent step, amides of Formula la can be converted to thioamides of Formula lb using a variety of standard thip transfer reagents including phosphorus.pentasulfide and Lawesson's reagent WO 01/70671 PCT/US01/09338 An alternate procedure for the preparation of compounds of Formula la involves coupling of an anthranilic amide of Formula 2 with an acid of Formula 4 in the presence of a 5 dehydrating agent such as dicyclohexylcarbodiimide (DCC). Polymer supported reagents are again useful here, such as polymer-bound cyclohexylcarbodiimide. Synthetic procedures of Schemes 1 and 2 are only representative examples of useful methods for the preparation . of Formula 1 compounds as-the synthetic literature is extensive for this type of reaction. 10 One skilled in the art will also realize that acid chlorides of Formula 3 may be prepared from acids of Formula 4 by numerous well-known methods. Anthranilic amides of Formula 2a are typically available from the corresponding 15 2-Ditrobenzamides of Formula 5 via catalytic hydrogenation of the nitro group. Typical procedures involve reduction with hydrogen in the presence of a metal catalyst such as palladium on carbon or platinum oxide and in hydroxylic solvents such as ethanol and isopropanol. These procedures are well documented in the chemical literature. R1 substituents such as alkyl, substituted alkyl and the like can generally be introduced at this 20 stage through known procedures including either direct alkylation or through the generally preferred method of reductive alkylation of the amine. A commonly employed procedure is to combine the aniline 2a with an aldehyde in the presence of a reducing agent such as sodium cyanoborohydride to produce the Formula 2b compounds where R1 is alkyl, alkenyl, aSk^nyl ox substituted derivatives thereof. WO 01/70671 PCTYUS01/09338 The intermediate amides of Formula 5a are readily prepared from commercially 5 available 2-nitrobenzoic acids. Typical methods for amide formation can be applied here. These include direct dehydrative coupling of acids of Formula 6 with amines of Formula 7 using for example DCC, and conversion of the acids to an activated form such as the acid chlorides or anhydrides and subsequent coupling with amines to form amides of Formula 5a. We have found ethylchloroformate to be an especially useful reagent for this type of reaction 10 involving activation of the acid. The chemical literature is extensive on this type of reaction. Amides of Formula 5a are readily converted to thioamides of Formula 5b by using commercially available thio transfer reagents such as phosphorus pentasulfide and Lawesson's reagent. 15 Benzoic acids of Formula 4 (J is optionally substituted phenyl) are generally well known in the art as are procedures for their preparation. One particularly useful subset of benzoic acids of this invention are 2-methyl-4-perfluoroalkyl benzoic acids of Formula 4a (R5 equals e.g. CF3, C2F5, C3F7). The synthesis for these compounds is outlined in 20 Schemes 5-9. Benzoic acids of Formula 4a may be prepared from the benzonitriles of Formula 8 by hydrolysis. The conditions used may involve the use of a base such as an alkaline metal hydroxide or alkoxide (e.g. potassium or sodium hydroxide) in a solvent such as water, ethanol or ethylene glycol (e.g. J. Chem. Soc. 1948,1025). Alternatively, the WO 01/70671 PCT/US01/09338 V. hydrolysis may be carried out using an acid such, as sulfuric acid or phosphoric acid in a suitable solvent such as water (e.g. Org. S^mth. 1955, Coll vol. 3, 557). The choice of the conditions is contingent on the stability of R5 to the reaction conditions and elevated . temperatures are usually employed to achieve this transformation. 5 Nitriles of Formula 8 may be prepared from anilines of Formula 9 by the classical sequence involving diazotization and treatment of the intermediate diazonium salt with a copper cyanide salt (e.g. J. Amer. Chem. Soc. 1902,24,1035). Scheme 6 Anilines of Formula 9 may be prepared from compounds of Formula 10. This 10 transformation may be achieved by a well-known procedure that employs Raney Nickel (Org. Synth. Coll. Vol VI, 581). Alternatively, the same transformation may be effected by the use of a suitable catalyst such as palladium in the presence of hydrogen. The reaction is visually conducted at pressures of 102 to 105 kPa in a suitable organic solvent such as, but not limited to, toluene. Elevated temperatures of 80-110°C are usually required to achieve 15 the transformation. As one skilled in the art will realize, numerous chemical modifications of the thioether moiety are possible, and may be employed when necessary to facilitate this transformation. WO 01/70671 PCT/US01/09338 Compounds of Formula 10 may be prepared from immosuliuranes of Formula 11. The transformation may be achieved in a protic solvent such as methanol or water, in a non-protic solvent such as dichloromethane or toluene in the presence of a suitable base such as triethylamine (e.g. Org. Synth. Coll. Vol. VI, 581) or sodium methoxide, or in a 5... /combination of a protic solvent, a protic solvent and a base. The temperature at which the reaction is conducted is usually in the range 40-110°C. As one skilled in the art will realize, suitable salts of compounds of Formula 11 such as, but not limited to a hydrochloride, a sulfate or a bisulfate may also be employed, provided that the appropriate amount of base is first used to generate the free base 11. This may be done as a separate step or as an integral 10 part of the step involving the transformation of compounds of Formula 11 to compounds of Formula 10. Compounds of Formula 11 may be prepared from anilines of Formula 12 by reaction with dimethyl sulfide and a suitable chlorinating agent such as, but not limited to 15 ' iV-cHorosuccinirtude (e.g. Org. Synth. Coll. Vol. VI, 581), chlorine or iV-chlorobenzotriazole. Alternatively, anilines of Formula 12 may be treated with dimethyl sulfoxide which has been "activated" by treatment with an agent such as acetic anhydride, trifluoroacetic, anhydride, trifluoromethanesulfonic anhydride, cyclohexylcarbodiimide, sulfur trioxide, or phosphorus pentoxide. The reaction is conducted in a.suitable organic 20 solvent such as dichloromethane or dimethyl sulfoxide. The reaction is conducted at a temperature of-70°C to 25°C and is dependent on the solvent and reagent used. WO 01/70671 PCT/US01/09338 Intermediate anthranilic amides of Formula 2a and 2b may also be prepared from isatoic anhydrides of Formula 13 and 14 (Scheme 10). Typical procedures involve combination of equimolar amounts of the amine 7 with the isatoic anhydride in polar aprotic 5 solvents such as pyridine and dimethylformamide at temperatures ranging from room temperature to 100° C. R1 substituents such as alkyl and substituted alkyl may be introduced by the base catalyzed alkylation of isatoic anhydride 13 with known alkylating reagents RJ-Lg (wherein Lg is a leaving group such as halogen, alkyl or aryl suphonates or alkyl sulfates) to provide the alkyl substituted intermediates 14. Isatoic anhydrides of Formula 13 10 may be made by methods described in Coppola, Synthesis 505-36 (1980). An alternate procedure for the preparation of specific compounds of Formula 1 (where A is Q, B is O and RJ is H) involves reaction of an amine 7 with a benzoxaainone of Formula 15. Typical procedures involve combination of the amine with the benzoxazinone 15 in solvents such as tetrahydrofuran or pyridine at temperatures ranging from room WO 01/70671 PCT/US01/09338 temperature to the reflux temperature of the solvent. Benzoxazinones are well documented in the chemical literature and are available via known methods that involve the coupling of either an anthranilic acid or an isatoic anhydride with an acid chloride. For references to the synthesis and chemistry of Benzoxazinones see Jakobsen et al, Biorgarde and Medicinal 5 Chemistry, 2000, 8, 2095-2103 and references cited within. See also Coppola, J, Heterocyclic Chemistry, 1999,36,563-588. Heterocyclic acids 4, where J is equal to an optionally substituted heterocycle, can be prepared by procedures outlined in Schemes 12-17. Both general and specific references to 10 a wide variety of heterocyclic acids including thiophenes, furans, pyridines, pyrimidines, triazoles, imidazoles, pyrazoles, thiazoles, oxazoles, isothiazoles, thiadiazoles, oxadiazoles, triazines, pyrazines, pyridazines, and isoxazoles can be found in the following compendia: Rodd's Chemistry of Chemistry of Carbon Compounds, Vol. IVa to IVL, S. Coffey editor, Elsevier Scientific Pubhshing, New York, 1973; Comprehensive Heterocyclic Chemistry, 15 Vol. 1-7, A. R. Katritzky and C. W. Rees editors, Pergamon Press, NewYork, 1984; Comprehensive Heterocyclic Chemistry II, Vol. 1-9, A. R. Katritzky, C. W. Rees, and E. F. Scriven editors, Pergamon Press, NewYork, 1996; and the series, The Chemistry of Heterocyclic Compounds, E. C. Taylor, editor, Wiley, New York. Particularly useful heterocyclic acids of this invention include pyridine acids, pyrimidine acids and pyrazole 20 acids. Procedures for the synthesis of representative examples of each are detailed in Schemes 12-17. A variety of heterocyclic acids and general methods for their synthesis may be found in World Patent Application WO 98/57397. The synthesis of representative pyridine acids (4b) is depicted in Scheme 12. This procedure involves the known synthesis of pyridines from p-ketoesters and 4- 25 aminobutenones (19), Substituent groups R7(a) and R7(b) include e.g. alkyl and haloalkyl. WO 01/70671 PCT/US01/09338 The synthesis of representative pyrimidine acids (4c) is depicted in Scheme 13. This procedure involves the known synthesis of pyrimidines from vinylidene-p-ketoesters (22) 5 and amidines. Substituent groups R7(a) and R7(b) include e.g. alkyl and haloalkyl. The synthesis of representative pyrazole acids (4d-4g) is depicted in Schemes 14-17. Pyrazoles 4d are described in Scheme 14. The synthesis of Scheme 14 involves as the keyWO 01/70671 PCT7US01/09338 step introduction of the R7(b) substituent via alkylation of the pyrazole. The alkylating agent R7(b)-Lg (wherein Lg is a leaving group such as CI, Br, I, sulfonates such as p-toluenesulfonate or methanesulfonate or sulfates such as -S02OR7(b)) includes R7(b) groups such as CrC6 alkyl, C2-C6 alkenyl, CyCs alkynyl, C3-C6 cycloalkyl, CrC6 haloalkyl, C2-5 C6 haloalkenyl, C2-C6 haloalkynyl, C3-Cg halocycloalkyl, C2-C6 alkylcarbonyl, C2-C6 alkoxycarbonyl, C3-Cg dialkylaminocarbonyl, C3-C6 trialkylsilyl; or phenyl, beazyl, benzoyl, 5- or 6-membered heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system, each ring or ring system optionally substituted. Oxidation of the methyl group affords the pyrazole carboxylic acid. Some of the more preferred R7(a) groups 10 include haloalkyl. Pyrazoles 4e are described in Scheme 15. These pyrazole acids may be prepared via metallation and carboxylation of pyrazoles of formula 28 as the key step. The R7(b) group is introduced in a manner similar to that of Scheme 14, i.e. via alkylation with a R7(b) 15 alkylating agent. Representative R7(a) groups include e.g. cyano, and haloalkyl. WO 01/70671 PCTVTJS01/09338 Pyrazoles 4f are described in Scheme 16. These can be prepared via reaction of an optionally substituted phenyl hydrazine 29 with a pyruvate 3 0 to yield pyrazole esters 31. Hydrolysis of the ester affords the pyrazole acids 4f. This procedure is particularly useful 5 for the preparation of compounds where R (b) is optionally substituted phenyl and R (a) is haloalkyl. WO 01/70671 PCT/US01/09338 Pyrazoles acids of Formula 4g are described in Scheme 17. These can be prepared via 3+2 cycloaddition of an appropriately substituted nitrilimine with either substituted propiolates (33) or acrylates (36). Cycloaddition with acrylates requires additional oxidation 5 of the intermediate pyrazoline to the pyrazole. Hydrolysis of the ester affords the pyrazole acids 4g. Preferred irninohalides for this reaction include the trifiuorornethyl irninochloride (38) and the irninodibromide (39). Compounds such as 38 are known (J. Heterocycl Chem. 1985,22(2), 565-8). Compounds such as 39 are available by known methods (Tetrahedron Letters 1999, 40,2605). These procedures are particularly useful for the preparation of 10 compounds where R7(b) is optionally substituted phenyl and R7(a) is haloalkyl or bromo. WO 01/70671 PCT/US01/09338 It is recognized that some reagents and reaction conditions described above for preparing compounds of Formula 1 may not be compatible with certain functionalities present in the intermediates. In these instances, the incorporation of protection/deprotection 5 sequences or functional group interconversions into the synthesis will aid in obtaining the desired products. The use and choice of the protecting groups will be apparent to one skilled in chemical synthesis (see, for example, Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991). One skilled in the art will recognize that, in some cases, after the introduction of a given reagent as it is depicted in any 10 individual scheme, it may be necessary to perform additional routine synthetic steps not described in detail to complete the synthesis of compounds of Formula 1. One skilled in the art will also recognize that it may be necessary to perform a combination of the steps illustrated in the above schemes in an order other than that implied by the particular sequence presented to prepare the compounds of Formula 1. WO 01/70671 PCT/US01/09338 One skilled in the art will also recognize that compounds of Formula 1 and the intermediates described herein can be subjected to various electrophilic, nucleophilic, radical, organometallic, oxidation, and reduction reactions to add substituents or modify existing substituents. 5 Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present invention to its fullest extent. The following Examples are, therefore, to be construed as merely illustrative, and not limiting of the disclosure in any way whatsoever. Percentages are by weight except for chromatographic solvent mixtures or where otherwise indicated. Parts and percentages for chromatographic 10 solvent mixtures are by volume unless otherwise indicated. H NMR. spectra are reported in ppm downfield from tetramethylsilane; s is singlet, d is doublet, t is triplet, q is quartet, m is multiplet, dd is doublet of doublets^dt is doublet of triplets, br s is broad singlet. EXAMPLE 1 Step A: Preparation of 3-memyl-A^O-memvlethvB-2-nitrobenzarnide 15 .A solution of 3-methyl-2-nitrobenzoic acid (2.00 g, 11.0 mmol) and triethylamine . (1.22 g, 12.1 mmol) in 25 mL of methylene chloride was cooled to 10°C. Ethyl chloroformate was carefully added and a solid precipitate formed. After stirring for 30 minutes isopropylarnine (0.94 g, 16.0 mmol) was added and a homogeneous solution resulted. The reaction was stirred for an additional hour, poured into water and extracted 20 with ethyl acetate. The organic extracts were washed with water, dried over magnesium sulfate and evaporated under reduced pressure to afford 1.96 g of the desired intermediate as a white solid melting at 126-128 °C. iHNMR (CDC13) 8 1.24 (d\6H), 2.38 (s,3H), 4.22 (m,lH), 5.80 (br s,lH), 7.4 (m,3H). StepB: Preparation of 2-amino-3 -methvl-JV-f 1 -methvletfayDbenzamide 25 The 2^nitrobenzamide of Step A (1.70 g, 7.6 mmol) was hydrogenated over 5% Pd/C in 40 mL of ethanol at 50 psi. When the uptake of hydrogen ceased the reaction was filtered through celite and the celite was washed with ether. The filtrate was evaporated under reduced pressure to afford 1.41 g of the title compound as a solid melting at 149-151 °C. !HNMR (CDCI3) 5 1.24 (dd,6H), 2.16 (s,3H), 4.25 (m,lH), 5.54 (br s72B), 5.85 (br 30 s,lH), 6.59 (UH), 7.13 (d,lH), 7.17 (d,lH). Step C: Preparation of 3-methvl-iV- rtrifluoromemoxv)berizovllarnmoTberizamide 4-(trifluoromethoxy)benzoyl chloride (0.29 g, 1.3 mmol) was added dropwise to a mixture of the aniline from Step B (0.25 g, 1.3 mmol) and triemylamine (0.13 g, 1.3 mmol) 35, in 5 mL of methylene chloride at room temperature. After stirring for one hour the reaction was poured into water and extracted with ethyl acetate. The combined extracts were dried over magnesium sulfate and evaporated under reduced pressure. The resulting solids were WO 01/70671 PCT/US01/09338 washed with hexane/ether and filtered to afford 0.41 g of the title compound, a compound of the present invention, as a solid melting at 207-209°C. 1HNMR (CDCI3) 6 1.19 (d, 6H), 2.33 (s, 3H), 4.15 (m, 1H), 5.97 (br d, 1H), 7.2-7.4 (m, 6H), 8.04 (d, 1H), 10.11 (br s51H). 5 EXAMPLE 2 Step A: Preparation of l-Ethvl-34rifluoromethylpyrazol-5-yl Carboxylic acid To a mixture of 3-trifiuoromethylpyrazole (5 g, 37 mmol) and powdered potassium carbonate (10 g, 72 mmol) stirring in 30 mL of i^iV-dimethylformamide, iodoethane (8 g, 51 mmol) was added dropwise. After a mild exotherm, the reaction was stirred overnight at 10 room temperature. The reaction mixture was partitioned between 100 mL of diethyl ether and 100 mL of water. The ether layer was separated, washed with water (3X) and brine, and dried over magnesium sulfate. Evaporation of solvent in vacuo gave 4 g of oil. To 3.8 g of this oil stirring in 40 mL of tetrahydrofuran under nitrogen in a dry ice/acetone bath, 17 mL of a 2.5 M solution of w-butyl lithium in tetrahydrofuran (43 mmol) 15 was added dropwise and the solution stirred for 20 minutes at -78°C. An excess of gaseous carbon dioxide was bubbled into the stirred solution at a moderate rate for 10 minutes. After addition of carbon dioxide, the reaction was allowed to slowly reach room temperature and stirred overnight. The reaction mixture was partitioned between diethyl ether (100 mL) and 0.5 N aqueous sodium hydroxide (100 mL). The basic layer was separated and acidified 20 with concentrated hydrochloric acid to a pH of 2-3. The aqueous mixture was extracted with ethyl acetate (100 mL) and. the organic extract washed with water and brine and dried over magnesium sulfate. The oily residue, which remained after evaporating the solvent in vacuo, was triturated to a solid from a small amount of H-butyl chloride. After filtering and drying, a slightly impure, sample of l-emyl-3-trifluoromethyl-pyrazol-5-yl carboxylic acid (1.4 g) 25 was obtained as a broad-melting solid. JH NMR (CDCI3): 9.85 (br s,lH), 7.23 (s,lH), 4.68 (q,2H), 1.51 (t,3H) ppm. Step B: Preparation of 2-[l-Ethvl-3-trifluoromethylpvrazol-5-vl carbamovl"l-3- methvl-iV-d -methvlethvDbenzamide To a solution of l-ethyl-3-trifluoromethyl-pyrazol-5-yl carboxylic acid (0.5 g, 30 2.4 mmol) stirring in 20 mL of methylene chloride, oxalyl chloride (1.2 mL, 14 mmol) was added. Upon addition of 2 drops of JV.iV'-dimethylfonnamide, foaming and bubbling occurred. The reaction mixture was heated at reflux for 1 hr as a yellow solution. After cooling, the solvent was removed in vacuo and the resulting residue dissolved in 20 mL of tetrahydrofuran. To the stirred solution, 2-amino-3-methyl-A^-(l-memylethyl)benzamide 35 (0.7 g, 3.6 mmol) was added followed by the dropwise addition of N,N- diisopropylemylarnine (3 mL, 17 mmol). After stirring at room temperature overnight, the reaction mixture was partitioned between ethyl acetate (100 mL) and IN aqueous WO 01/70671 PCT/US01/09338 hydrochloric acid (75 mL). The separated organic layer was washed with water and brine and dried over magnesium sulfate. Evaporating in vacuo gave a white solid residue, which on purification by flash column chromatography on silica gel (2:1 hexanes/ethyl acetate) afforded 0.5 g of the title compound, a compound of the present invention, melting at 5 223-226°C. ^NMRCDMSO-De): 10.15 (s,lH), 8.05 (d,lH), 7.45 (s,lH), 7.43-7.25 (m,3H), 4.58 (q,2H), 3.97 (m,lH), 2.45 (ss3H), 1.36 (t,3H), 1.06 (d,6H) ppm. EXAMPLE 3 Step A: Preparation of S.S-dimemvl-i\T-[4-rtrifluoromemvDphenvl]sulfilimine 10 A solution of N-cMorosucciinmide (12-43 g, 93.1 mmol) in ~170 mL of dichloromethane was added to a mixture of 4-(trifluoromethyl) aniline (15 g, 93.1 mmol) and dimethyl sulfide (6.35 g, 102 mmol) in 230 mL of dichloromethane at-5-0°C. After the addition was complete, the mixture was stirred at 0-5°C for lh, and iV-chlorosuccinrmide (0.02 g, 4.64 mmol) was added. After a further 30 minutes, the mixture was washed with 15 500 mL of IN sodium hydroxide. The organic phase was dried and evaporated to give the product as a solid 19-72 g melting at 101-103 °C (after crystallization from ethyl acetate/hexanes). rR(Nujol) 1603,1562,1532,1502,1428,1402,1335,130Q, 1270,1185, 1150,1103, 1067,1000, 972, 940, 906, 837, 817 cm"1. 20 lB NMR"(CDC13) 5 7.35 (d, J=8.8 Hz, 2 H), 6.84 (d, J=8.8 Hz, 2 H), 2.67 (5,3 H). Step B: 2-[rmethylthio^methvl1-4-(rtrffluoromethvl)benzenamine . Sodium methoxide in methanol (1.95 g, 9.02 mmol, 25%) was added to S,S-dimemyl-A^-[4-(trifluoromemyl)phenyl]sulfm^nine from Step A (2 g, 9.04 mmol) in 15 mL of toluene. The mixture was warmed to ~80°C for -1 h. The mixture was allowed to cool to 25 25°C and was poured into 100 mL of water. The mixture was extracted with 2x100 mL of ethyl acetate and the combined extracts were dried and evaporated to give 1.8 g of the product as a solid melting at 65.5-67.5°C (after crystallization from hexanes). IR(nujol) 3419, 3333,1629,1584,1512,1440,1334,1302,1235,1193,1139,1098, 1078, 979, 904, 832 cm"1. 30 !HNMR (CDC13) 5 7.35 (dd, J=1.5 Hzx 8.2 Hz, 1H) 6.72 (d, J=8.4 Hz) 4.39 (br.5, 2 H, 3.69 (5,2 H), 1.99 (5,3 H). Step C: Preparation of 2-methvl-4-rtrifluoromethvl)benzenamine Activated Raney nickel (500 g wet paste, ~50u) was added portionwise to a solution of 2-[(memyltMo)memyl]-4-(1rifluoromemyi)benzenamme (55.3 g, 0.25 mole) in 1 L of 35 ethanol over 30 minutes at 25-30° C. The heterogeneous mixture was stirred vigorously for 30 minutes after the addition. The stirring was stopped, and the solids were allowed to settle over one hour. The liquid was decanted from the solids and poured through filter paper. WO 01/70671 PCT/US01/09338 The filtrate was evaporated under reduced pressure, and the residue was taken up in dichloromethane. The organic phase was separated from a small volume of water, dried over magnesium sulfate and evaporated under reduced pressure to afford 37.6g of the title compound as amber oil. 5 !HNMR (CDGI3) 5 7.28 (m,2H), 6.68 (d,lH), 3.87 (br s,2H), 2.19 (s,3H). Step D: Preparation of 2-me1hvl-44trifluoromethvl>)benzonitrile Concentrated hydrochloric acid (16 mL) was added dropwise at a moderate rate to a heterogeneous mixture of 2-methyl^(triiluoromemyl)benzenamine (14 g, 80 mmol) and 120 mL of water while stirring vigorously. A thick suspension resulted which was stirred for 10 20 minutes, diluted with 280 mL of water and cooled to 5° C. A solution of sodium nitrite (5.5 g, 80 mmol) and 25 mL of water was added slowly to the reaction suspension. After stirring for 30 minutes at 5° C a solution resulted which was stirred cold for 30 more minutes and then neutralized with potassium carbonate. This diazonium salt solution was then added portionwise via cannula to a stirred, 95 ° C mixture of potassium cyanide (22 g, 0.34 mole), 15 copper sulfate pentahydrate (20 g, 80 mmol) and 140 mL of water. After the addition the mixture was stirred for 30 minutes at 95° C and then allowed to cool to room temperature. Ether was added and the heterogeneous mixture was filtered through celite. The solids were washed with ether, and the filtrate was partitioned. The aqueous phase was extracted with ether, and the combined organic extracts were dried over magnesium sulfate and 20 concentrated under reduced pressure to afford 13.1 g of the title compound as brown oil. ]H NMR (CDCI3) 8 7.74 (d,lH), 7.60 (s,lH), 7.55 (d,lH), 2.64 (s,3H). Step E: Preparation of 2-methvl-4-trifluoromethyl benzoic acid Potassium hydroxide (15.7 g, 0.28 mole) and 15 mL of water were added as a solution to a stirred, heterogeneous mixture of 2-memyl^(trifluoromemyl)benzordtrile (13 25 g, 70 mmol) and 135 mL of ethylene glycol. The reaction mixture was heated at 120-130° C for 20 hours and allowed to cool to room temperature. The dark solution was poured into 800 mL of water and filtered through celite. The filtrate was washed with ether and then the aqueous was acidified with concentrated hydrochloric acid. This aqueous phase was extracted three times with ethyl acetate, the organic extracts were combined, dried over 3 0 magnesium sulfate and evaporated under reduced pressure to afford the title compound as a tan solid. H NMR (CDCI3) 5 7.98 (d,lH), 7.70 (s,lH), 7.65 (d,lH), 2.60 (s,3H). Step F: Preparation of 2-methvl-4-rtrifluoromethoxv')benzovl chloride Thionyl chloride (0.42 g, 3.5 mmol) was added to a solution of the benzoic acid from 35 Step E (0.50 g, 2.4 mmol) in 10 mL of toluene at room temperature. The reaction was refiuxed for three hours then cooled to room temperature. The solvent was evaporated under reduced pressure and excess thionyl chloride was removed by azeotroping with toluene. The benzoyl chloride obtained was used directly in Step G. WO 01/70671 PCT/US01/09338 Step G: Preparation of 2-methvl-JV-r2-metfavl-6-rrn -me&vlethvDaminol-- carbonvl]phenvl1-44trifluorometfavl'>beDzamide The benzoyl chloride of Step F (0.29 g, 1.3 mmol) was added to a mixture of the aniline from Example 1, Step B (0.36 g, 1.9 mmol) and diisopropylethylamine (0.26 g, 5 2.0 mmol) in 10 mL of chloroform at room temperature. The reaction was allowed to stir ovemight The solid precipitate was filtered and dried to afford 0.38 g of the title compound, a compound of the present invention, as a solid melting at 247-248 °C. lH NMR (CDC13) a 1.24 (d,6H), 2.41 (s,3H), 2.58 (s,3H), 4.20 (m,lH), 5.94 (br d,lH), 7.2-7.3 (m,2H), 7.40 (d,lH), 7.52 (s,lH), 7.53 (d,lH), 7.70 (d,lH), 9.36 (br s,lH). 10 EXAMPLE 4 Step A: Preparation of 2-Methvl-6-ftrifluoromethvlV3-rjvridinecarbonyl chloride Thionyl chloride (4.35 g, 36.5 mmol) was added to a mixture of 2-methyl-6- trifluoromethyl nicotinic acid (5.00 g, 24.4 mmol) in 75 mLof toluene and the mixture was heated at reflux for 3 hours. The reaction was cooled to room temperature and the solvent 15 was removed under reduced pressure. Excess thionyl chloride was removed by azeotrope with toluene. The resultant acid chloride was used as is in Example 4, Step B. Step B: Preparation of 8-Memvl-2-r2-memvl-6-fMfluoromethvlV3-Pvridinvl")-4^- 3,1-benzoxazine A mixture of the 6-methyl isatoic anhydride (3.92 g, 22.1 mmol) and the acid 20 cMoride from Step A (5.45 g, 24.3 mmol) was heated at reflux in pyridine for 16 hours. The dark brown solution was cooled to room temperature and the solvent was removed under reduced pressure. Excess pyridine was removed by azeotrope with toluene. Ether was added and the resulting brown solid was removed by filtration. The solid was taken up in a mixture of aqueous sodium bicarbonate and chloroform, the chloroform extracts were dried 25 over magnesium sulfate and evaporated. Excess pyridine was again removed by azeotrope with toluene to afford 5.1 g of the title compound as a brown solid. ]H NMR (CDCI3) d 2.65 (s,3H), 3.11 (s,3H), 7.49 (t,lH) 7.40 (m,lH), 7.68-7.73 (m,2H), 1.11 (d,lH), 8.58 (d,lH). Step C: Preparation of 2-Methvl-JV-r2-methvl-6-rr(l- 30 methvlemvl)ammo]carbonvl1phenvll-6-(trifluoromethvlV3-pyridine Isopropylarnine (7.37 g, 0.125 mmol) was added to a mixture of the benzoxadnone of Step B (4.00 g, 12.5 mmol) in 30 mL of tetrahydrofuran. A homogeneous solution formed. The mixture was heated briefly after which a thick white precipitate formed. The solvent was removed under reduced pressure and the resultant solid was washed with ether 35 and filtered to afford 4.48 g of the title compound as a solid melting at 247-248 C. !H NMR (CDCI3) d 1.24 (d,6H), 2.41 (s,3H), 2.77 (s,3H), 4.17 (m,lH), 5.96 (bd,lH), 7.21 (m,2H) 7.40 (m,lH), 7.53 (d,lH), 7.97 (d,lH), 9.80 (bs,lH). WO 01/70671 PCT/US01/09338 EXAMPLES Step A: Preparation of 4-Methvl-JV-r2-methvl-6-rra- methvletavnaminolcaTbonvllphenvIj^-faifluoroniethylVS- pyrimidinecarboxamide 5 To a solution 0.8 g (4 mmol) of 4-methyl-2-trifluoromethylpyrimidine-5-carboxylic acid [made by the method of Palanki et als J.Med. Chem. 2000,43, 3995] stirring in 15 mL of methylene chloride, oxalyl chloride (2 mL, 23 mmol) was added. Upon addition of 2 drops of iV^iV'-dimethylformamide, foaming and bubbling occurred. The reaction mixture was heated at reflux for 1 hr as a yellow solution. After cooling, the solvent was removed in 10 vacuo and the resulting residue dissolved in 20 mL of tetrahydrofuran. To the stirred solution, 2-amino-3-memyl-iV-(l-memylethyl)benzamide (1 g, 5 mmol) was added followed by the drop wise addition of N.N-du^opropylemylarnine (3 ml, 17 mmol). After stirring at room temperature overnight, the reaction mixture was partitioned between ethyl acetate (200 mL) and IN aqueous hydrochloric acid (75 mL). The separated organic layer was 15 washed with water and brine and dried over magnesium sulfate. Evaporating in vacuo gave a white solid, which was suspended in a small amount of ethyl acetate and filtered to afford (after drying) 650 mg of the title compound, a compound of the present invention, melting at 248-251°C. 'HNMR (DMSO-D6): 10.3 (s,NH), 9.07 (s,lH), 8.25 (d,NH), 7.43-7.25 (m,3H), 4.03 20 (m,lH);2.73 (s,3H), 2.32 (s,3H), 1.12 (d,6H) ppm. EXAMPLE 6 . Step A: Preparation of 2-Memyl-l-phenvl-4-('trifluoromethvlVlff-pvrazole A solution of l,l,l-trifl.uoropentane-2,4-dione (20.0 g, 0.130 mole) in glacial acetic acid (60 mL) was cooled to 7°C using an ice/water bath. Phenylhydrazine (14.1 g, 0.130 25 mole) was added dropwise over a period of 60 minutes. The reaction mass temperature increased to 15°C during the addition. The resulting orange solution was held under ambient conditions for 60 minutes. The bulk of the acetic acid was removed by stripping on a rotary evaporator at a bath temperature of 65°C. The residue was dissolved in methylene chloride (150 mL). The solution was washed with aqueous sodium bicarbonate (3 g in 50 mL water). 30 The purple-red organic layer was separated, treated with activated charcoal (2 g) and MgS04, then filtered. Volatiles were removed on a rotary evaporator. The crude product consisted of 28.0 g of a rose-colored oil, which contained ~89% the desired product and 11 % 1 -phenyl-5-(trifluoromethyl)-3-methylpyrazoIe. ^NMR (DMSO-De) 5 2.35 (s,3H), 6.76 (s,lH), 7.6-7.5 (m,5H). WO 01/70671 PCT/US01/09338 StepB: Preparation of l-Phenvl-3-(trifluoromethyD-lij'-pvrazole-5-carboxvlic ar.id A sample of crude l-phenyl-3-(trifJuoromethyl)-5-methylpyrazole (~89%, 50.0 g, 0.221 mole) was mixed with water (400 mL) and cetyltrimemylammonium chloride (4.00 g, 0.011 mole). The mixture was heated to 95°C. Potassium permanganate was added in 10 5 equal portions, spaced at -8 minute intervals. The reaction mass was maintained at 95-100°C during this period. After the last portion was added, the mixture was held for ~15 minutes at 95-100°C, whereupon the purple, permanganate color had been discharged. The reaction mass was filtered while hot (~75°C) through a 1 cm thick bed of Celite® on a 150 ml, coarse, glass frit. The filter cake was washed with warm (~50°C) water (3xlO0mL). 10 The combined filtrate and washings were extracted with ether (2x100 mL) to remove a small amount of yellow, water-insoluble material. The aqueous layer was purged with nitrogen to remove residual ether. The clear, colorless alkaline solution was acidified by adding concentrated hydrochloric acid dropwise until the pH reached ~1.3 (28 g, 0.28 mole). Gas evolution was vigorous during the first two-thirds of the addition. The product was collected 15 via filtration, washed with water (3x40 mL), then dried overnight at 55°C in vacuo. The product consisted of 11.7 g of a white, crystalline powder, which was essentially pure based upon £[ NMR. ]H NMR (CDC13) 8 7.33 (s,lH), 7.4-7.5 (m,5H). Step C: Preparation of l-Phenvl-S-rtrifluoromethvlVlff-pvrazole-S-carbonyl chloride 20 A sample of crude l-phenyl-3-(trifluoromethyl)pyrazole-5-carboxyhc acid (4.13 g, 16.1 mmol) was dissolved in methylene chloride (45 mL). The solution was treated with oxalyl chloride (1.80 mL, 20.6 mmol), followed by A^A^dimethylformamide (0.010 mL, 0.13 mmol). Off-gassing began shortly after adding the i^AT-dimethylformamide catalyst. The reaction mixture was stirred for ~20 minutes under ambient conditions, then was heated to 25 reflux for a period of 35 minutes. Volatiles were removed by stripping the reaction mixture on a rotary evaporator at a bath temperature of 55°C. The product consisted of 4.43 g of a light-yellow oil. The only impurity observed by H NMR was i^iV"-dmethylformamide. lHNMR (CDCI3) 8 7.40 (m,lH), 7.42 (s,lH), 7.50-7.53 (m,4H). Step D: Preparation of JV'-r2-Memvl-6-[fri-methvlemvnarnmo'\|carbonyllphenyl]-l- 30 phenyl-3-(trifluoromemvlVlH-pvrazole-5-carboxamide A sample of 3-methylisatoic anhydride (0.30 g, 1.7 mmol) partially dissolved in pyridine (4.0 mL) was treated with l-phenyl-3-(trifluoromethylpyrazole)-5-carboxyl chloride (0.55 g, 1.9 mmol). The mixture was heated to ~95°C for a period of 2 hours. The resulting orange solution was cooled to 29°C, then was treated with isopropylarnine (1.00 g, 16,9 35 mmol). The reaction mass self-heated to 39°C. It was further heated to 55°C for a period of 30 minutes, whereupon much precipitate formed. The reaction mass was dissolved in • methylene chloride (150 mL). The solution was washed with aqueous acid (5 mL cone. HC1 in 45 mL water), then with aqueous base (2 g sodium carbonate in 50 mL water). The WO 01/70671 PCT/US01/09338 organic layer was dried over MgS04, filtered, then concentrated on a rotary evaporator. Upon reduction to ~4 mL, product crystals had formed. The slurry was diluted with -10 mL of ether, whereupon more product precipitated. The product was isolated by filtration, washed with ether (2x10 mL), then washed with water (2x50 mL). The wet cake was dried 5 for 3 0. minutes at 70°C in vacuo. The product consisted of 0.52 g of an off-white powder melting at 260-262°C. 2H NMR (DMSO-D6) 5 1.07 (d,6H), 2.21 (s,3H), 4.02 (octet,lH), 7.2-7.4 (m,3H), 7.45-7.6 (m,6H), 8.10 (d,lH), 10.31 (s,lH). EXAMPLE 1' 10 Step A: Preparation of 3-Trifluorome&vl-2-r3-(triiluoromethvlVlff-nvrazol-l" yllpyridine A mixture of 2-chloro-3-trifluoromethylpyridine (3.62 g., 21 mmol), 3- trifluoromethylpyrazole (2.7 g., 20 mmol), and potassium carbonate (6.0 g., 43 mmol) were heated at 100 ° C for 18 h. The cooled reaction mixture was added to ice/water (100 mL). 15 The mixture was extracted twice with ether (100 mL) and the combined ether extracts were washed twice with water (100 mL). The organic layer was dried with magnesium sulfate and concentrated to an oil. Chromatography on silica gel with hexanes:ethyl acetate 8:1 to 4:1 as eluent gave the title compound (3.5 g) as an oil. XHNMR (CDC13) 5 6.75 (m,lH), 7.5 (m,lH), 8.2 (m,2H), 8.7 (m,lH). 20 Step B: Preparation of 3-(Trifluoromethyl)-l-[3-(trifluoromethvlV2-pyriduivll-lH- pyrazole-5-carboxylic acid A mixture of the title compound of Example 5, Step A (3.4 g, 13 mmol) was dissolved in tetrahydrofuran (30 mL) and cooled to - 70 °C. Lithium diisopropylamide ( 2N in heptane/tetrahydrofuran, (Aldrich) 9.5 mL, 19 mmol) was added and the resulting dark 25 mixture was stirred for 10 minutes. Dry carbon dioxide was bubbled through the mixture for 15 minutes. The mixture was allowed to warm to 23 °C and treated with water (50 mL) and 1 N sodium hydroxide (10 mL). The aqueous mixture was extracted with ether (100 mL) and then ethyl acetate (100 mL). The aqueous layer was acidified with 6JVhydrochloric acid to pH 1-2 and extracted twice with dichloromethane. The organic layer was dried with 30 magnesium sulfate and concentrated to give the title compound (1.5 g). !H NMR (CDC13) 5 7.6 (m,lH), 7.95 (m,lH), 8.56 (m,lH), 8.9 (m,lH), 14.2 (br,lH) Step C: Preparation of Ar-r2-Methvl-6-["[ri -methyiemyl)amino1carbonvllphenyll-3- ffrifluoromemvl)-l-[3-ftrifluorome^ carboxamide 35 A mixture of the title compound of Example 5, Step B (0.54 g, 1.1 mmol), the title compound from Example 1, Step B (0.44 g, 2.4 mmol) and bop chloride (bis(2-oxo-oxazoHd^yl)phosphinyl chloride, 0.54 g, 2.1 mmol) in acetonitrile (13 mL) was treated with WO 01/70671 PCT/US01/09338 triethylamine (0.9 mL). The mixture was shaken in a closed scintillation vial for 18 h. The reaction was partitioned between ethyl acetate (100 mL) and lJVhydrochloric acid. The ethyl acetate layer was washed successively with IN hydrochloric acid (50 mL), IN sodium hydroxide (50 mL) and saturated sodium chloride solution (50 mL). The organic layer was 5 dried over magnesium sulfate and concentrated. The residue was subjected to column chromatography on silica gel with hexanes/ethyl acetate (5:1 to 3:1) as eluent. The title compound (0.43 g) was isolated as a white solid. in.p. 227 -230 °C. 2HNMR (CDC13) 5 1.2 (m, 6H), 4.15 (m, 1H), 5.9 (br d,lH), 7.1 (m,lH), 7.2 (m,2H), 7.4 (s,lH), 7.6 (m,lH), 8.15 (m,lH), 8.74 (m,lH), 10.4 (br,lH). 10 By the procedures described herein together with methods known in the art, the following compounds of Tables 1 to 17 can be prepared. The following abbreviations are used in the Tables: t is tertiary, s is secondary, n is normal, / is iso, c is cyclo, Me is methyl, Et is ethyl, Pr is propyl, /-Pr is isopropyl, M3u is tert butyl, Ph is phenyl, OMe is methoxy, OEt is ethoxy, SMe is methylthio, SEt is ethylthio, CN is cyano, N02 is nitro, 15 TMS is trimethylsilyl, S(0)Me is methylsulfuryl, and S(0)2Me is methylsulfonyl. 52 WO 01/70671 PCT/US01/09338 Formulation/Utility Compounds of this invention will generally be used as a formulation or composition with an agriculturally suitable carrier comprising at least one of a liquid diluent, a solid diluent or a surfactant. The formulation or composition ingredients are selected to be , • 5 consistent with the physical properties of the active ingredient, mode of application and environmental factors such, as soil type, moisture and temperature. Useful formulations include liquids such as solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions and/or suspoemulsions) and the like which optionally can be thickened into gels. Useful formulations further include solids such as dusts, 10 powders, granules, pellets, tablets, films, and the like which can be water-dispersible ("wettable") or water-soluble. Active ingredient can be (micro)encapsulated and further formed into a suspension or solid formulation; alternatively the entire formulation of active ingredient can be encapsulated (or "overcoated"). Encapsulation can control or delay release of the active ingredient. Sprayable formulations can be extended in suitable media and used 15 at spray volumes from about one to several hundred liters per hectare. High-strength compositions are primarily used as intermediates for further formulation. The formulations will typically-contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges that add up to 100 percent by weight. Weight Percent Active Ingredient Diluent Surfactant Water-Dispersible and Water- 5-90 0-94 1-15 soluble Granules, Tablets and Powders. Suspensions, Emulsions, 5-50 40-95 0-15 Solutions (including Emulsifiable Concentrates) Dusts 1-25 70-99 0-5 Granules and Pellets 0.01-99 5-99.99 0-15 High Strength Compositions 90-99 0-10 0-2 Typical solid diluents are described in Watkins, et al., Handbook of Insecticide Dust 20 Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950. McCutcheon 's Detergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, New Jersey, as well as Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. WO 01/70671 PCT/US01/09338 Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth and the like, or thickeners to increase viscosity. Surfactants include, for example, polyethoxylated alcohols, polyethoxylated 5 alkylphenols, polyethoxylated sorbitan fatty acid esters, dialkyl sulfosuccinates, alkyl sulfates, alkylbenzene sulfonates, organosilicones, A^-dialkyltaurates, lignin sulfonates, naphthalene sulfonate formaldehyde condensates, polycarboxylates, and. polyoxyethylene/polyoxypropylene block copolymers. Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, starch, sugar, silica, talc, 10 diatomaceous earth, urea, calcium carbonate,.sodium carbonate and bicarbonate, and sodium sulfate. Liquid diluents include, for example, water, iV^-dimqthylformarnide, dimethyl sulfoxide, iV-alkylpyrrolidone, ethylene glycol, polypropylene glycol, paraffins, alkylbenzenes, alkylnaphthalenes, oils of olive, castor, linseed, rung, sesame, corn, peanut, cotton-seed, soybean, rape-seed and coconut, fatty acid esters, ketones such as 15 cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, and alcohols such as methanol, cyclohexanol, decanol and tetrahydrofurfuryl alcohol. Solutions, including emulsifiable concentrates, can be prepared by simply mixing the ingredients. Dusts and powders can be prepared by blending and, usually, grinding as in a hammer mill or fluid-energy mill. Suspensions are usually prepared by wet-milling; see, for 20 example, U.S. 3,060,084. Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, "Agglomeration", Chemical Engineering, December 4,1967, pp 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and following, and WO 91/13546. Pellets can be prepared as described in U.S. 4,172,714. 25 Water-dispersible and water-soluble granules can be prepared as taught in U.S. 4,144,050, U.S. 3,920,442 and DE 3,246,493. Tablets can be prepared as taught in U.S. 5,180,587, U.S. 5,232,701 and U.S. 5,208,030. Films can be prepared as taught in GB 2,095,558 and U.S. 3,299,566. For further information regarding the art of formulation, see U.S. 3,235,361, Col. 6, 30 line 16 through Col. 7, line 19 and Examples 10-41; U.S. 3,309,192, Col. 5, line 43 through Col. 7, line 62 and Examples 8,12,15,39,41, 52, 53, 58,132,138-140,162-164, 166, 167 and 169-182; U.S. 2,891,855, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pp 81-96; and Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific 35 Publications, Oxford, 1989. . In the following Examples, all percentages are by weight and all formulations are prepared in conventional ways. Compound numbers refer to compounds in Index Tables A. WO 01/70671 PCT/US01/09338 Example A Wettable Powder Compound 1 65.0% dodecylphenol polyethylene glycol ether 2.0% 5 sodium ligninsulfonate 4.0% sodium silicoaluminate 6.0% montmoriUonite (calcined) 23.0%. Example B Granule 10 Compound 1 10.0% attapulgite granules (low volatile matter, 0.71/0.30 mm; U.S.S. No. 25-50 sieves) 90.0%. Example C Extruded Pellet 15 Compound 1 25.0% anhydrous sodium sulfate 10.0% crude calcium Hgninsulfonate 5.0% sodium allcylnaphmalenesulfonate 1.0% calcium/magnesium bentonite 59.0%. 20 Example D Emulsifiable Concentrate Compound 1 20.0% blend of oil soluble sulfonates and polyoxyethylene ethers 10.0% 25 isophorone 70.0%. The compounds of this invention exhibit activity against a wide spectrum of foliar-feeding, -fruit-feeding, stem or root feeding, seed-feeding, aquatic and soil-inhabiting arthropods (term "arthropods" includes insects, mites and nematodes) which are pests of growing and stored agronomic crops, forestry, greenhouse crops, ornamentals, nursery crops, 30 stored food and fiber products, livestock, household, and public and animal health. Those skilled in the art will appreciate that not all compounds are equally effective against all growth stages of all pests. Nevertheless, all of the compounds of this invention display activity against pests that include: eggs, larvae and adults of the Order Lepidoptera; eggs, foliar-feeding, fruit-feeding, root-feeding, seed-feeding larvae and adults of the Order 35 Coleoptera; eggs, irnmatures and adults of the Orders Hemiptera and Homoptera; eggs,' larvae, nymphs and adults of the Order Acari; eggs, irnmatures and adults of the Orders Thysanoptera, Orthoptera and Dermaptera; eggs, irnmatures and adults of the Order Diptera; WO 01/70671 PCT/US01/09338 and eggs, juveniles and adults of the Phylum Nematoda. The compounds of this invention are also active against pests of the Orders Hyrnenoptera, Isoptera, Siphonaptera, Blattaria, Thysanura and Psocoptera; pests belonging to the Class Arachnida and Phylum Platyhekrrinthes. Specifically, the compounds are active against southern com rootworm 5 (Diabrotica undecimpunctata howardi), aster leafhopper (Mascrostelesfascifrons), boll weevil (Anthonomus grandis), two-spotted spider mite (Tetranychus urticae), fall armyworm (Spodopterafrugiperda), black bean aphid (Aphis fabae), green peach aphid (Myzus persica), cotton aphid (Aphis gossypii), Russian wheat aphid (Diuraphis noxia), English grain aphid (Sitobion avenae), whitefly (Bemisia tabacif), tobacco budworm (Heliothis 10 virescens), rice water weevil (Lissorhoptrus oryzophilus), rice leaf beetle (Oulema oryzae), whitebacked planthopper (Sogatellafurciferd), green leafhopper (Nephotettix cincticeps), brown planthopper (Nilaparvata lugens), small brown planthopper (LaodeJphax striatellus), rice stem borer (Chilo suppressalis), rice leafroller (Cnaphalocrocis medinalis). black rice stink bug (Scotinophara lurida), rice stink bug (Oebalus pugnax), rice bug (Leptocorisa 15 chinensis), slender rice bug (Cletuspuntiger), southern green stink bug (Nezara viridula) and german cockroach (Blatella germanicd). The compounds are active on mites, demonstrating ovicidal, larvicidal and chemosterilant activity against such families as Tetranychidae including Tetranychus urticae, Tetranychus cinnabarinus, Tetranychus mcdanieli, Tetranychus pacificus, Tetranychus turkestani, Byrobia rubrioculus, Panonychus ulmi, 20 Panonychus citri, Eotetranychus carpini borealis, Eotetranychus, hicoriae, Eotetranychus sexmaculatus, Eotetranychus yumensis, Eotetranychus banksi and Oligonychus pratensis; Tenuipalpidae including Brevipalpus lewisi, Brevipalpus phoenicis, Brevipalpus californicus and Brevipalpus obovatus; Eriophyidae including Phyllocoptruta oleivora, Eriophyes sheldoni, Aculus cornutus, Epitrimerus pyri and Eriophyes mangiferae. See WO 90/10623 25 and WO 92/00673 for more detailed pest descriptions. Compounds of this invention can also be mixed with one or more other insecticides, fungicides, nematocides, bactericides, acaricides, growth regulators, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants or other biologically active compounds to form a multi-component pesticide giving an even broader spectrum of 30 agricultural protection. Examples of such agricultural protectants with which compounds of this invention can be formulated are: insecticides such as abamectin, acephate. avermectin, azinphos-methyl, bifenthrin, buprofezin, carbofuran, chlorfenapyr, chlorpyrifos, chlorpyrifos-methyl, clothianidin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, cypermethrin, deltamethrin, diafenthiuron, diazinon, diflubenzuron, 35 dimethoate, diofenolan, emamectin, endosulfan, esfenvalerate, fenothiearb, fenoxycarb, fenpropathrin, fenvalerate, fipronil, flucythrinate, tau-fluvalinate, flufendxuron, fonophbs, imidacloprid, isofenphos, malathion, metaldehyde, methamidophos, methidathion, methomvl. methonrene. methoxvchlor. methvl 7-chloro-2,5-dihydro-2-[[AT- WO 01/70671 PCT/US01/09338 (methoxycarbonyl)-^-^ (tiMuorometboxy)phenyl]aii)ino]carbonyl]iiideno[l ,2-e][l ,3,4]oxadkzine-4a(3#)-carboxylate (mdoxacarb),'monocrotophos, oxamyl, parathion, paratbion.-metb.yl, permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos, pymetrozine, 5 pyriproxyphen, rotenone, spionsad, sulprofos, tebufenozide, tefluthrin, terbufos, tetraGhlorvinphos, thiacloprid, tbiodicarb, tralomethrin, trichlorfon and triflumuron; fungicides such, as acibenzolar, azoxystrobin, benomyL, blasticidin-S, Bordeaux mixture (Tribasic copper sulfate), bromuconazole, carpropamid (KTU 3616), captafol, captan, carbendazun, chloroneb, chlorothalonil, copper oxychloride, copper salts, cymoxanil, 10 cyproconazole, cyprodinil (CGA 219417),(1S)-3,5-dichloro-iV-(3H;hloro-l-ethyl-l-methyl- 2-oxopropyl)-4-metiiylbenzamide (RH 7281), diclocymet (S-2900), diclomezine, dicloran, difenoconazole5(S)-3,5-aUhydro-5-memyl-2-(methyltHo)-5-phenyl~3-(phenylamino)-4i?-imidazol-4-one (RP 407213), dimethomorph, diniconazole, diniconazole-M, dodine, edifenphos, epoxiconazole (BAS 480F), famoxadone, fenamidone, fenarimol, 15 fenbuconazole, fencaramid (SZX0722), fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, fluazJnam, fludioxonil, flumetover (RPA 403397), fluquinconazole, flusilazole, flutolanil, flutriafol, folpet, fosetyl-aluminum, furalaxyl, furametapyr (S-82658), hexaconazole, ipconazole, iprobenfos, iprodione, isoprothiolane, kasugamycin, kresoxim-methyl, mancozeb, maneb, mefenoxam, mepronil, metalaxyl, 20 metconazole, metommostrobin/fenoniinostrobin (SSF-126), myclobutanil, neo-asozin (ferric methanearsonate), oxadixyl, penconazole, pencycuron, probenazole, prochloraz, propamocarb, propiconazole, pyrifenox, pyraclostrobin, pyrimethanil, pyroquilon, quinoxyfen, spiroxamine, sulfur, tebuconazole, tetraconazole, thiabendazole, thifiuzamide, thiophanate-methyl, thiram, triadimefon, triadimenol, tricyciazole, trifioxystrobin, 25 triticonazole, .validamycin and vinclozolin; nematocides such as aldicarb, oxamyl and fenamiphos; bactericides such as streptomycin; acaricides such as amitraz, chinornethionat, chlorobenzilate, cyhexatin, dicofol, dienochlor, etoxazole, fenazaquin, fenbutatin oxide, fenpropathrin, fenpyroximate, hexythiazox, propargite, pyridaben and tebufenpyrad; and biological agents such as Bacillus thuringiensis, Bacillus thicringiensis delta endotoxin, 30 . baculovirus, and entomopathogenic bacteria, virus and fungi. Preferred insecticides and acaricides for mixing with compounds of this invention include pyrethroids such as cypeimethrin, cyhalothrin, cyflufbrin and beta-cyfluthrin, esfenvalerate, fenvalerate and tralomethrin; carbamates such as fenothicarb, methomyl, oxamyl and thiodicarb; neonicotinoids such as clothianidin, imidacloprid and thiacloprid, 35 neuronal sodium channel blockers such as indoxacarb, insecticidal macrocyclic lactones such as spinosad, abamectin, avermectin and emamectin; GAB A antagonists such as endosulfan and fipronil; insecticidal ureas such as flufenoxuron and triflumuron, juvenile hormone mimics such as diofenolan and pyriproxyphen; pymetrozine; and amitraz. WO 01/70671 PCT/US01/09338 Preferred biological agents for mixing with compounds of this invention include Bacillus thuringiensis and Bacillus tkuringiensis delta endotoxin. , Most preferred mixtures include a mixture of a compound of this invention with cyhalothrin; a mixture of a compound of this invention with beta-cyfluthrin; a mixture of a 5 compound of this invention with esfenvalerate; a mixture of a compound of this invention with methomyl; a mixture of a compound of this invention with imidacloprid; a mixture of a compound of this invention with thiacloprid; a mixture of a compound of this invention with indoxacarb; a mixture of a compound of this invention with abamectin; a mixture of a compound of this invention with endosulfan; a mixture of a compound of this invention with 10 fipronil; a mixture of a compound of this invention with flufenoxuron; a mixture of a compound of this invention with pyriproxyphen; a mixture of a compound of this invention with; a mixture of a compound of this invention with pymetrozine; a mixture of a compound of this invention with amitraz; a mixture of a compound of this invention with Bacillus thuringiensis and a mixture of a compound of this invention with Bacillus thuringiensis delta 15 endotoxin. In certain instances, combinations with other arthropodicides having a similar spectrum of control but a different mode of action will be particularly advantageous for resistance management. Arthropod pests are controlled and protection of agronomic, horticultural and 20 specialty crops, animal and human health is achieved by applying one or more of the . compounds of this invention, in an effective amount, to the environment of the pests including the agronomic and/or nonagronomic locus of infestation, to the area to be protected, or directly on the pests to be controlled. Thus, the present invention further comprises a method for the control of foliar and soil inhabiting arthropods and nematode 25 pests and protection of agronomic and/or nonagronomic crops, comprising applying one or more of the compounds of the invention, or compositions containing at least one such compound, in an effective amount, to the environment of the pests including the agronomic and/or nonagronomic locus of infestation, to the area to be protected, or directly on the pests to be controlled. A preferred method of application is by spraying. Alternatively, granular 30 formulations of these compounds can be applied to the plant foliage or the soil. Other methods of application include direct and residual sprays, aerial sprays, seed coats, microencapsulations, systemic uptake, baits, eartags, boluses, foggers, fumigauts, aerosols, dusts and many others. The compounds can be incorporated into baits that are consumed by-the arthropods or in devices such as traps and the like. 3 5 The compounds of this invention can be applied in their pure state, but most often application will be of a formulation comprising one or more compounds with suitable carriers, diluents, and surfactants and possibly in combination with a food depending on the contemplated end use. A preferred method of application involves spraying a water WO 01/70671 PCI7US01/09338 dispersion or refined oil solution of the compounds. Combinations with spray oils, spray oil concentrations, spreader stickers, adjuvants, other solvents, and synergists such as piperonyl butoxide often enhance compound efficacy. The rate of application required for effective control will depend on such factors as 5 the species of arthropod to be controlled, the pest's life cycle, life stage, its size, location, time of year, host crop or animal, feeding behavior, mating behavior, ambient moisture, temperature, and the like. Under normal circumstances, application rates of about 0.01 to 2 kg of active ingredient per hectare are sufficient to control pests in agronomic ecosystems, but as little as 0.001 kg/hectare may be sufficient or as much as 8 kg/hectare may be 10 required. For nonagronomic applications, effective use rates will range from about 1.0 to 50 mg/square meter but as little as 0.1 mg/square meter may be sufficient or as much as 150 mg/square meter may be required. The following TEST demonstrates the control efficacy of compounds of tins invention on specific pests. "Control efficacy" represents inhibition of arthropod 15 development (including mortality) that causes significantly reduced feeding. The pest control protection afforded by the compounds is not limited, however, to these species. See Index Tables A through Q for compound descriptions. The following abbreviations are used in the Index Tables which follow: t is tertiary, n is normal, i is iso, c is cyclo, s is secondary, Me is methyl, Et is ethyl, Pr is propyl, i-Pr is isopropyl, c-Pr is cyclopropyl, Bu is butyl, s- 20 Bu is secondary butyl, Pent is pentyl, OMe is methoxy, OEt is ethoxy, SMe is methylthio, SEt is ethylthio, CN is cyano, N02 is nitro, and Het is heterocycle. The abbreviation "Ex." stands for "Example" and is followed by a number indicating in which example the compound is prepared. 25 B is O, except where indicated Compound R1 R2 R3 R4 Rs and/or R6 m.p. °C l(Exl) H i-Pr H 2-Me 4-OCF3 . 207-209 WO 01/70671 PCT/US01/09338 a 1H NMR data are in ppm downfield from tetramethylsilane. Couplings are designated by (s)-singlet, (d)-doublet, (t)-triplet, (q)-quartet, (m)-multiplet, (dd)-doublet of doublets, (dt)~doiiblet of triplets, (br s)-broad singlet. . BIOLOGICAL EXAMPLES OF THE INVENTION TEST Application: Compounds are formulated in a 10% acetone, 90% water and 300 ppm X-77 surfactant solution, unless otherwise indicated. The formulated compounds are applied 5 with a SUJ2 atomizer nozzle with 1/8 JJ custom body (Spraying Systems) positioned Vi' above the top of each test unit There are 6 of these nozzles that make up the spray boom and this is fixed in a belt sprayer. A rack (or carrier) of 6 different insect test units is placed on the conveyor belt and stops so that each unit is centered under a nozzle. Once the rack is centered, 1 mL of liquid is sprayed into each test unit; the rack then continues down the belt 10 to the end of the sprayer to be off-loaded. All experimental compounds in this screen are sprayed at 250 ppm and replicated three times. Diamondback Moth (DBM) - Plutella Xylostella: The test unit consists of a small self-contained unit with a 12-14 day old radish plant inside. These are pre-infested (using a core sampler) with 10-15 neonate larvae on apiece of insect diet. Once 1 mL of formulated 15 compound has been sprayed into each test unit, the test units are allowed to dry for 1 hour before a black, screened cap-is placed on the top of the cylinder. They are held for 6 days in a growth chamber at 25 °C and 70% relative humidity. Plant feeding damage was visually assessed on a scale of 0-10 where 0 is no feeding, 1 is 10% or less feeding, 2 is 20% or less feeding, 3 is 30% or less feeding through a 20 maximum score of 10 where 10 is 100% of foliage consumed. Of the compounds tested the following provided excellent levels of plant protection (ratings of 0-1,10% or less feeding damage): 1,2, 3,4, 6,7,9,10,13,14,15,19,20,24, 27,28,29, 30,31,32, 33, 35,' 37,38, 39, 51, 52, 53, 60, 61, 62, 63, 64, 65,66, 68, 69, 72,73, 74, 75,76, 79, 80, 84, 86, 88, 89,90, WO 01/70671 PCT/US01/09338 ^ 92,96, 97,98,99,100,101,102,103,107,113,124,126,127,143,144,146,147,148,150, 151,152,153,158,159,160,161,162,16.3,164,165,166,167,169,170,171,174,183, 184,185, 186,187,188,189,190,191,193,194,195,196,198,202,203,204,205,206, 207,208, 209,210,211,212,213,214,215,216,217,218,219,220,222,223,225,227, ' 5 228,229, 230,231,232,233,235,238,239,240,244,245,246,248,249,250,251,252, 253,256, 257,275,276,277,278, B2, B4, B5, B6, B7, B8, B9, BIO, Bll, B12, B13, B14, B15, B16, B17, B18, B19, B20, B21, B23, B24, B25, B28, B29, B30, B31, B32, B33, B35, B37, B38, B39, B40, B42, B43, B44, B45, B46, B47, B48, B49, B50, B53, B55, B57, B58, B59, B60, B61, B62, B63, B64, B66, B67, B68, B69, B70, B71, B72, B74, B75, B76, CI, 10 C2, C3, C4, C5, C7, C8, C9, CIO, CI 1, C12, C79, D2, D3,D4, D5, D6, D7, D8, Dll, D12, D13, D14, D15, D16, D18, D19, D20, D23, D24, D25, D26, D27, D28, D29, D30, D32, D33, D34, D37, D38, D39, D40, D41, D42, D45, D46, D47, D48, D50, D51, D52/D53, D54, D55, D56, D57, D58, D59, D60, D61, D62, D63, D64, D65, D66, D67, D68, D69, D70, D71, D72, D73, D74, D75, D76, D77, D78, D79, D81, D83, D84, D85, D86, D87, 15 D88, D89, D91, D92, D93, D94, D95, D96, D97, Dill, D113, D114, D115, D116, D117, D118, D119, D120, D121, D122, D123, D124, D125, D126, D162, D164, E4, F2, F5, F6, F7, F8, G2, G3, G5, HI, H2, H3, H4, J3, J4,16, Ml, M3, N2 and PL We claim: 1. A method for controlling arthropods comprising contacting the arthropods 01 their environment with an arthropodicidally effective amount of a compound of Formula 1, its TV-oxide or agriculturally suitable salts wherein A and B are independently 0 or S; each J is independently a phenyl or naphthyl group substituted with 1 to 2 R-"" and optionally substituted with 1 to 3 R6; or each J is independently a 5- or 6-membered heteroaromatic ring or an aromatic 8-, 9- or I O-membered fused heterobicyclic ring system wherein-each ring or ring system is optionally substituted with 1 to 4 R7; n is 1 to 4, R1 is H; or CrC() alkyl, C2-C6 alkenyl, C2-C6 alkynyl or C3~C6 cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, N02, hydroxy. CrC4 alkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C[-C4 alkylsulfonyl, C2~C4 alkoxycarbonyl, CpC4 alkylamino. C2-C^ dialkylamino and C^-C^, cycloalkylamino; or R1 is C2-Q, alkylcarbonyl, C2-C(y alkoxycarbonyl, C2-CV> alkylaminocarbonyl. CrC8 dialkylaminocarbonyl or C(=A)J; R2 is H, C,-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, CrC4 alkoxy, C\-C+ alkylamino, C2-Cx dialkylamino, C^-Q, cycloalkylamino. C2-C6 alkoxycarbonyl or C2-C6 alkylcarbonyl; R3 is H; G; CrC6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-Cf) cycloalkyl, each optionally substituted with one or more substituents selected from the group consisting of halogen, G, CN, N02, hydroxy, CrC4 alkoxy, CrC4 haloalkoxv, C y-C j,alkylthio, Ci,-C4alkylsulfinyl. Gj^C^alkylsulfonyL CrC^ alkoxycarbonyl, C2-C6 alkylcarbonyl, C3-C6 trialkylsilyl, and a phenyl, phenoxy or 5- or 6-membered heteroaromatic ring, each ring optionally substituted with one to three substituents independently selected from the group consisting of CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, CrC4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyi, halogen, CN, NO2, C1-C4 alkoxy, C1-C4 haloalkoxy, CpC4 alkylthio, CrC4 alkylsulfinyl, CpC4 alkylsulfonyl, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C3-C6 (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl and C3-Q3 trialkylsilyl; Q-C4 alkoxy; Ci-C4 alkylamino, C2-C8 dialkylamino; C3-Q, cycloalkylamino; C2-C^ alkoxycarbonyl or C2-Q, alkylcarbonyl; or R2 and R' can be taken together with the nitrogen to which they are attached to form a ring containing 2 to 6 atoms of carbon and optionally one additional atom o\' nitrogen, sulfur or oxygen, said ring may be optionally substituted with 1 to 4 substituents selected from the group consisting of Ci-C2 alkyl, halogen. CN, N02 and C1-C2 alkoxy; G is a 5- or 6-membered nonaromatic carbocyclic or heterocyclic ring, optionally including one or two ring members selected from the group consisting of C( 0). SO or S(0)2 and optionally substituted with 1 to 4 substituents selected from the group consisting of Ci-C2 alkyl, halogen, CN, N02 and Cj-C2 alkoxy. each R~* is independently H, Cj-Q, alkyl, C2-C C2-C6 alkoxycarbonyl, C2-Cg alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl or C3-C6 trialkylsilyl; each R5 is independently CrC6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, CrC6 halocycloalkyl, CN, N02, CrC4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, C1-C4 alkylsulfonyl, C!-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, Cj-C6 haloalkylsulfonyl, Ci-C4 alkylamino, C2-Cs dialkylamino, or CrC6 cycloalkylamino, C2-C6 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, or C3-C8 dialkylaminocarbonyl; or (fl5)2 when attached to adjacent carbon atoms can be taken together as -OCF20-, -CF2CF20-. or -OCF2CF20-; each R6 is independently H, halogen, Cj-Q, alkyl. C2-Cr) alkenyl, C2-C6 alkynyl, C3-C(j cycloalkyl, Ct-C4 alkoxy or C2-C4 alkoxycarbonyl; or each R6 is independently a phenyl, benzyl, phenoxy. 5- or 6-membered heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system, each ring optionally substituted with one to three substituents independently selected from the group consisting of CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, CrC6 cycloalkyl, C,-C4 haloalkyl, C2-C4 haloalkenyl. C2-C4 haloalkynyl, CyC() halocycloalkyl, halogen, CN. N02, CrC4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl. Ci-C4 alkylsulfonyl, C\|-C4 alkylamino, C2-C8 dialkylamino, CyCb cycloalkylamino, C^-CV, (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl. C2-Cf, alkoxycarbonyl, C2-C6 alkylaminocarbonyl, CyC$ dialkylaminocarbonyl and CrCG trialkylsilyl; each R7 is independently H, C]-Cf) alkyl, C2-CG alkenyl, C2-C^ alkynyl, CyC(, cycloalkyl. CrC6 haloalkyl, C2-C6 haloalkenyl, C2-C(, haloalkynyl. CyC() halocycloalkyl, halogen, CN, C02H, CONH2, N02, hydroxy, CrC4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, CrC4 alkylsulfonyl, CrC4 haloalkylthio, C\|-C4 haloalkylsulfinyl, C\|-C4 haloalkylsulfonyl, C]-C4 alkylamino, C2-Cg dialkylamino, CyC() cycloalkylamino, C2-C6 alkylcarbonyl, C2-Cf) alkoxycarbonyl, C2-Cf) alkylaminocarbonyl, C_--Cg dialkylaminocarbonyl, or C^-Q, trialkylsilyl. or each R7 is independently a phenyl, benzyl, benzoyl, phenoxy, 5- or 6-membered heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system, each ring optionally substituted with one to three substituents independently selected from the group consisting of CpC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, CrC4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, N02, CrC4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, Cr C4 alkylsulfonyl, CrC4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C3-C6 (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl and C3-C provided that J is other than an optionally substituted 1,2,3-thiadiazole. 2. The method as claimed in 1 wherein J is a phenyl group substituted with I to 2 R5 and optionally substituted with 1 to 3 R6 3. The method as claimed in 2 wherein A and B are both O. n is 1 to 2; R1 is H, C,-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-Cf, cycloalkyl, C2-C„ alkylcarbonyl or C2-Q, alkoxycarbonyl; R2 is H, CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, CrC6 alkylcarbonyl or C2-Cf, alkoxycarbonyl; R3 is C\|-Cc alkyl. C2-Q, alkenyl, C2-Q, alkynyl or C3-C(j cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, Cj-C2 alkoxy, Cj-C2 alkylthio, CpC2 alkylsulfinyl and Cj-C2 alkylsulfonyl; one of the R4 groups is attached to the phenyl ring at the 2-position or 5-position, and said R4 is C,-C4 alkyl, CrC4 haloalkyl, halogen, CN, N02, CrC4 alkoxy, CpC4 haloalkoxy, Cj-C4 alkylthio, C)-C4 alkylsulfinyl, Cj-C4 alkylsulfonyl, Cj-C4 haloalkylthio, CpC4 haloalkylsulfinyl, or CpC4 haloalkyl sulfonyl; each R5 is independently C^-C^ haloalkyl, CN, N02, CrC4 haloalkoxy, CrC4 alkylthio. C\-C^ alkylsulfinyl, C\|-C4 alkylsulfonyl, Cj-C4 haloalkylthio, Cp C4 haloalkylsulfinyl, C\|-C4 haloalkylsulfonyl or C2-C4 alkoxycarbonyl; or (R-"02 when attached to adjacent carbon atoms can be taken together as -OCFTO-, -CF2CF20- or -OCF2CF20-; and each R6 is independently H, halogen, Ct-C4 alkyl, CpC2 alkoxy or C2-C4 alkoxycarbonyl, or each R6 is independently a phenyl or a 5- or 6-membered heteroaromatic ring, each ring optionally substituted with CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl. c3-c6 cycloalkyl, CrC4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, N02, C1-C4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio, C1-C4 alkylsulfinyl, CrC4 alkylsulfonyl, CrC4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C3-C6 (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-CG alkylaminocarbonyt, C3-C8 dialkylaminocarbonyl or C3-C6 trialkylsilyl. 4. The method as claimed in 3 wherein Rl and R2 are both H; R3 is CrC4 alkyl optionally substituted with halogen, CN, OCH3, or S(0)pCH3; each R4 is independently H, CH3, CF3, OCF3, OCHF2, S(0)pCF3, S(0)pCHF2. CN or halogen; each R5 is independently CF3, OCF3, OCHF2, S(0)pCF3, S(0)pCHF2. OCH:CF3, OCF2CHF2. S(0)pCH2CF3 or S(0)pCF2CHF2; each R6 is independently H, halogen or methyl; or phenyl, pyrazole, imidazole, triazole. pyridine or pyrimidine, each ring optionally substituted with C1-C4 alkyl, C1-C4 haloalkyl, halogen or CN; and p is 0, 1 or 2. 5. The method as claimed in 4 wherein R3 is /-propyl or /-butyl. 6. The method as claimed in 1 wherein J is a 5- or 6-membered heteroaromatic ring optionally substituted with 1 to 4 R7. 7. The method as claimed in 6 wherein .1 is a 5- or 6-membered heteroaromatic ring selected from the group consisting of J-l, J-2. J-3. J-4 and J-5, each J optionally substituted with 1 to 3 R7 Q is O, S or NRT; and W, X, Y and Z are independently N or CR7, provided that in J-4 and J-5 at least one ofW, X,YorZisN. 8. The method as claimed in 6 or 7 wherein A and B are O; n is 1 to 2; R1 is H, CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C2-C6 alkylcarbonyl or C2-C6 alkoxycarbonyl; R2 is H, CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C2-C6 alkylcarbonyl or C2-C(j alkoxycarbonyl; R^1 is H; or CrCfi alkyl, C2-Cr, alkenyl, C2-C6 alkynyl or CrC6 cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, C\|-C2 alkoxy, C[-C2 alkylthio, CpC2 alkylsulfinyl and C\|-C2 alkylsulfonyl; one of the R4 groups is attached to the phenyl ring at the 2-position, and said R4 is C,-C4 alkyl, C,-C4 haloalkyl, halogen, CN, N02, CrC4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, CrC4 alkylsulfonyl, CrC4 haloalkylthio, CrC4 haloalkylsulfinyl or CpQ haloalkylsulfonyl; and each R7 is independently H, CrC4 alkyl, CrC4 haloalkyl, halogen, CN, N02, Cr C4 haloalkoxy, C\-C^ alkylthio, CrC4 alkylsulfinyl, CrC4 alkylsulfonyl, CrC4 haloalkylthio, CrC4 haloalkylsulfinyl, CpC4 haloalkylsulfonyl or C2-C4 alkoxycarbonyl; or a phenyl or a 5- or 6-membered heteroaromatic ring, each ring optionally substituted with C]-C4 alkyl, C2-C4 alkenyl. C2-C4 alkynyl, CrQ, cycloalkyl, CrC4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, CrC6 halocycloalkyl, halogen, CN, N02, C,-C4 alkoxy, C,-C4 haloalkoxy. C,-C4 alkylthio, CrC4 alkylsulfinyl, C,-C4 alkylsulfonyl, C,-C4 alkylamino, C2-Cg dialkylamino, C^-C^ cycloalkylamino, C^-C^ (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-Cf, alkoxycarbonyl, C2-Cf, alkylaminocarbonyl, C^-C^ dialkylaminocarbonyl or C3-Q-, trialkylsilyl. 9. The method as claimed in 8 wherein J is selected from the group consisting of pyridine, pyrimidine, pyrazole, imidazole, triazole, thiophene, thiazole and oxazole, furan, isothiazole and isoxazole, each optionally substituted with 1 to 3 R7. 10. The method as claimed in 9 wherein J is selected from the group consisting of pyridine, pyrimidine, pyrazole, thiophene and thiazole, each optionally substituted with 1 to 3 R7; R1 and R2 are both H; R?1 is C,-C4 alkyl optionally substituted with halogen, CN, OCH3, or S(0)pCH3; each R4 is independently H, CH3) CF3, OCF3, OCHF2, S(0)pCF3, S(0)pCHF2, CN or halogen; each R7 is independently H, halogen, CH3, CF3, OCHF2, S(0)pCF3, S(0)pCHF2, OCH2CF3. OCF2CHF2, S(0)pCH2CF3, S(0)pCF2CHF2; or phenyl, pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted with C,-C4 alkyl, C,-C4 haloalkyl, CrC4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, CrC4 alkylsulfonyl, halogen or CN; and p is 0, 1 or 2. 11 The method as claimed in 10 wherein J is a pyridine optionally substituted with I to 3 R12. The method as claimed in 11 wherein one R7 is a phenyl optionally substituted with C\|-C4 alkyl, CrC4 haloalkyl, halogen or CN. 13. The method as claimed in 11 wherein one R7 is a pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted with Cj-C4 alkyl, C\|-C4 haloalkyl, halogen or CN. 14. The method as claimed in 10 wherein J is a pyrimidine optionally substituted with 1 to 3 R7. 15. The method as claimed in 14 wherein one R7 is a phenyl optionally substituted with C\|-C4 alkyl, CrC4 haloalkyl, halogen or CN. 16. The method as claimed in 14 wherein one R7 is a pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted with C]-C4 alkyl. C(-C4 haloalkyl, halogen or CN 17. The method as claimed in 10 wherein J is a pyrazole optionally substituted with 1 to 3 R7 18. The method as claimed in 17 wherein one R7 is a phenyl optionally substituted with C\-C+ alkyl, C\|-C4 haloalkyl, halogen or CN. 19. The method as claimed in 17 wherein one R7 is a pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted with CpC4 alkyl, CpC4 haloalkyl, halogen or CN. 20. The method as claimed in 19 wherein R7 is a pyridine optionally substituted with C \|-C4 alkyl, C i-C4 haloalkyl. halogen or CN 21. The method as claimed in 1 comprising a compound of Formula 1 selected from the group consisting of: 3-methyl-A'-( l-methylethyl)-2-[[4-(trifluoromethyl)benzoyl]amino]-benzamide, 2-methyl-A-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-4- (trifluoromethyl)benzamide. 2-methyl-JV-[2-methyl-6-[[(l-methylethyI)amino]carbonyl]phenyl]-6- (trifluoromethyl)-3-pyridinecarboxamide, \ -ethyl-N-[2-methyl-64[( 1 -methylethyl)amino]carbonyl]phenyl}-3 - (trifluoromethyl)-l//-pyrazoIe-5-carboxamide, l-(2-fluorophenyl)-A^-[2-methyl-6-[[(l-methylethyl)amino)carbonyl]phenyl]-3- (trifluoromethyl)-l//-pyrazole-5-carboxarnide, 1 -(3-chloro-2-pyridinyl)-A42-methyl-6-[[(l - methylethyl)amino]carbonyl]phenyl]3-(trifluoromethyl)-l/f-pyrazole-5-carboxamide, A^-[2-chloro-6-[[(l-methylethyl)amino]carbonyl]phenyl]-l-(3-chloro-2-pyridinyl)-3-(trit1uoromethyl)-l//-pyrazoIe-5-carboxamide, 3-bromo-1 -(2-chlorophenyl)-A^-[2-methyl-6-[[( 1 -methylethyl)amino]carbonyl]phenyl]-l//-pyrazole-5-carboxamide, and 3-bromo-A-[2-chloro-6-[[(l-niethylethyl)amino]carbonyl]phenyl]-l-(2-chlorophenyl)-l//-pyrazole-5-carboxamide. 22. A compound of Formula \, its N-oxides and agriculturally suitable salts wherein A and B are independently O or S; each J is independently a phenyl or naphthyl group substituted with 1 to 2 R-" and optionally substituted with 1 to 3 R6; or each J is independently a 5- or 6-membered heteroaromatic ring or an aromatic 8-,c)- or 10-membered fused heterobicyclic ring system wherein each ring or ring system is optionally substituted with 1 to 4 R7; n is 1 to 4; R1 is H; or Cj-C(- alkyl, C2-Q alkenyl, C2-Q, alkynyl or C^-Cc cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, N02, hydroxy, CrC4 alkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, CrC4 alkylsulfonyl, C2-C4 alkoxycarbonyl, CrC4 alkylamino, C2-C8 dialkylamino and C3-C6 cycloalkylamino; or R1 is C2-C6 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C R2 is H, CrC6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, CrC4 alkoxy, CrC4 alkylamino, C2-C8 dialkylamino, C3-C R3 is H; CrC6 alkyl, C2-CG alkenyl, C2-C6 alkynyl, CrC optionally substituted with one or more substituents selected from the group consisting of halogen, CN, N02, hydroxy, C1-C4 alkoxy, C[-C4 haloalkoxy, C,-C4 alkylthio. C,-C4 alkylsulfinyl, C,-C4 alkylsulfonyl, C2-C(, alkoxycarbonyl, C2-C(, alkylcarbonyl, C3-Q trialkylsilyl, and a phenoxy ring optionally substituted with one to three substituents independently selected from the group consisting of C)-C4 alkyl, C2-C4 alkenyl, C2~C4 alkynyl, Cy Cf, cycloalkyl. CrC4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, Cy C() halocycloalkyl, halogen, CN, N02, CpC4 alkoxy, Cj-C4 haloalkoxy, Cp C4 alkylthio. Cj-C4 alkylsulfinyl, Cj-C4 alkylsulfonyl, Cj-C4 alkylamino, Cj-C-x dialkylamino, CyC(} cycloalkylamino, C3-Cg (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-Cf, alkoxycarbonyl, C2-Q$ alkylaminocarbonyl, Cy Cs dialkylaminocarbonyl and CyC() trialkylsilyl; C]-C4 alkoxy; Cj-C4 alkylamino. C2-Cx dialkylamino; CyC(} cycloalkylamino; C2-C6 alkoxycarbonyl or C2-Q, alkylcarbonyl; or R2 and R-' can be taken together with the nitrogen to which they are attached to form a ring containing 2 to 6 atoms of carbon and optionally one additional atom of nitrogen, sulfur or oxygen, said ring may be optionally substituted with 1 to 4 substituents selected from the group consisting of CpC2 alkyl, halogen, CN. N02 and CrC2 alkoxy; each R4 is independently H, C.\-C,(i alkyl, C2-C6 alkenyl, C2-C(-, alkynyl, CyC() cycloalkyl. CrC(, haloalkyl, CrC6 haloalkenyl, C2-C6 haloalkynyl. CrC6 halocycloalkyl. halogen, CN, N02, hydroxy, CrC4 alkoxy, CrC4 haloalkoxy. CrCA alkylthio, C,-C4 alkylsulfinyl, CrC4 alkylsulfonyl, CrC4 haloalkylthio. CrC4 haloalkylsulfinyl, CrC4 haloalkylsulfonyl, CrC4 alkylamino. C2-Cg dialkylamino, CyC(y cycloalkylamino, or CyC^ trialkylsilyl: or each R4 is independently phenyl, benzyl or phenoxy, each optionally substituted with CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, CrC4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, N02, CrC4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, Cj-C4 alkylsulfonyl, CrC4 alkylamino, C2-Cg dialkylamino, C3-C6 cycloalkylamino, C3-C6 (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-CG alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl or C3-C6 trialkylsilyl; each R5 is independently Cj-Q, haloalkyl, C2-C.6 haloalkenyl, C2-C6 haloalkynyl, CrC6 halocycloalkyl, CrC4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, CrCi alkylsulfonyl, CrC4 haloalkylthio, C,-C4 haloalkylsulfinyl, CrC4 haloalkylsulfonyl, CN. N02, C\|-C4 alkylamino. C2-Cs dialk\ lamino, C^-Q, cycloalkylamino, C2-Q alkylcarbonyl, C2-C() alkoxycarbonyl, C-rQ, alkylaminocarbonyl, or C3-C8 dialkylaminocarbonyl; or (R^b attached to adjacent carbon atoms can be taken together as -OCF20-, -CF2CF:0-, or -OCF2CF20-; each R6 is independently H, halogen, CpC^ alkyl, C2-C each R6 is independently a phenyl, benzyl, phenoxy. 5- or 6-membered heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system, each ring optionally substituted with one to three substituents independently selected from the group consisting of CpC4 alkyl, C2-C4 alkenyl, C2-C+ alkynyl, CrC6 cycloalkyl, CrC4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C(-) halocycloalkyl, halogen, CN, N02, CrC4 alkoxy, C,-C4 haloalkoxy, C^ alkylthio, C,-C4 alkylsulfinyl, CrC4 alkylsulfonyl, CrC4 alkylamino, C2-Cx dialkylamino, C3-Cf, cycloalkylamino, C3-Q, (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-Cf, alkoxycarbonyl, C2-C dialkylaminocarbonyl and C-?-Cf, trialkylsilyl; each R7 is independently H, CpCf, alkyl, C2-Cf) alkenyl, C2-C(> alkynyl, C3-Cf) cycloalkyl. C\|-Q, haloalkyl, C2-C6 haloalkenyl, C2-C(-) haloalkynyl, C-j-Q halocycloalkyl, halogen, CN, C02H, CONH2, N02, hydroxy, C,-C4 alkoxy, CrC4 haloalkoxy, C\|-C4 alkylthio, CrC4 alkylsulfinyl, CrC4 alkylsulfonyl, CrC4 haloalkylthio, CrC4 haloalkylsulfinyl, CrC4 haloalkylsulfonyl, Cj-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C2-CG alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl, or C3-C6 trialkylsilyl; or each R7 is independently a phenyl, benzyl, benzoyl, phenoxy or 5- or 6-membered heteroaromatic ring or an 8-, 9- or 10-membered fused heterobicyclic ring system, each ring optionally substituted with one to three substituents independently selected from the group consisting of C]-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, CrC4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, N02, CrC4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfmyl, Cr C4 alkylsulfonyl, CrC4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C3-Q, (alkyl)cycloalkylamino. C2-C4 alkylcarbonyl. C2-C6 alkoxycarbonyl, C2-Q, alkylaminocarbonyl, CvCg dialkylaminocarbonyl and C3-Cc, trialkylsilyl; provided that (i) at least one R4 and at least one R7 are other than H: (ii) J is other than an optionally substituted 1,2,3-thiadiazole;. (iii) when J is an optionally substituted pyridine and R2 is H, R"1 is other than H or CH3; (iv) when J is an optionally substituted pyridine, then R7 cannot be CONH2, C2-Cf, alkylaminocarbonyl or C^-C^ dialkylaminocarbonyl; and (v) when J is an optionally substituted pyrazole, tetrazole or pyrimidine, then R2 and R-" cannot both be hydrogen. 23, The compound as claimed in 22 wherein J is a phenyl group substituted with 1 to 2 R? and optionally substituted with 1 to 3 R6. 24. The compound as claimed in 23 wherein A and B are both 0; n is 1 to 2; R' is H, CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, CVC6 alkylcarbonyl or C2-C(, alkoxycarbonyl; R2 is H, C,-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl. C3-C6 cycloalkyl, C\-C6 alkylcarbonyl or C2-Cc, alkoxycarbonyl: R' is C\-C() alkyl. C2-Q, alkenyl, C2-CV, alkynyl or C3-Cf, cycloalkyl each optionalK' substituted with one or more substituents selected from the group consisting of halogen, CN, C)-C2 alkoxy, C]-C2 alkylthio, CpC? alkylsulfmyl and C1-C2 alkylsulfonyl; one of the R4 groups is attached to the phenyl ring at the 2-position Or 5-position, and said R4 is CrC4 alkyl, CrC4 haloalkyl, halogen, CN, N02, CrC4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio, Ci-C4 alkylsulfinyl, CrC4 alkylsulfonyl, CrC4 haloalkylthio, CrC4 haloalkylsulfinyl or CrC4 haloalkylsulfonyl; each R5 is independently CrC4 haloalkyl, CN, N02, CrC4 haloalkoxy, CrC4 alkylthio. CrC4 alkylsulfinyl, CrC4 alkylsulfonyl, CrC4 haloalkylthio, Cr C4 haloalkylsulfinyl, CpC4 haloalkylsulfonyl or C2-C4 alkoxycarbonyl; or (R-",)2 when attached to adjacent carbon atoms can be taken together as -OCF20-, -CF2CF20- or -OCF2CF20-; and each R6 is independently H, halogen, C1-C4 aikyl, CpC2 alkoxy or C2-C4 alkoxycarbonyl, or each R6 is independently a phenyl or.a 5- or 6-membered heteroaromatic ring, each ring optionally substituted with CpC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, CrC6 cycloalkyl, CrC4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-Q, halocycloalkyl, halogen, CN, N02, CpC4 alkoxy, Cj-C4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, CpC4 alkylsulfonyl, CpC4 alkylamino, C2-C8 dialkylamino, CrC6 cycloalkylamino, C3-C6 (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, Cr Cs dialkylaminocarbonyl or C^-C^ trialkylsilyl. 25 The compound as claimed in 24 wherein R' and R2 are both H; R' is CrC4 alkyl optionally substituted with halogen, CN, OCH3, or S(0)pCH3; each R4 is independently H, CH3, CF3, OCF3, OCHF2, S(0)pCF3, S(0)pCHF2, CN or halogen; each R5 is independently CF3, OCF3, OCHF2, S(0)pCF3, S(0)pCHF2. OCH2CF3, OCF2CHF2, S(0)pCH2CF3 or S(0)pCF2CHF2; each Rf) is independently H, halogen or methyl; or phenyl, pyrazole, imidazole, triazole. pyridine or pyrimidine, each ring optionally substituted with C)-C4 alkyl, C j-C4 haloalkyl, halogen or CN; and p is 0, I or 2 2d The compound as claimed in 25 wherein R^ is /-propyl or /-butyl. 27 The compound as claimed in 22 wherein J is a 5- or 6-membered heteroaromatic ring optionally substituted with 1 to 4 R7. 28. The compound as claimed in 27 wherein J is a 5- or 6-membered heteroaromatic ring selected from the group consisting of J-l, J-2, J-3, J-4 and J-5, each J optionally substituted with 1 to 3 R7 QisO, SorNR7;and VV, X, Y and Z are independently N or CR~. provided that in J-4 and J-5 at least one ofW, X, YorZisN. 29. The compound as claimed in 27 or Claim 28 wherein A and B are O; n is 1 to 2; R1 is H, C\|-C4 alky I, Cj-C.^ alkenyl, C2-C4 alkynyl, C2-C6 alkylcarbonyl or C2-Q, alkoxycarbonyl; R2 is H, C,-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, CrC6 cycloalkyl. C:-C(, alkylcarbonyl or C2-C(, alkoxycarbonyl. R^ is H; or C(-C6 alkyl, C2-Q, alkenyl, C2-C{, alkynyl or C3-Q, cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen. CN, C\|-C2 alkoxy, C]-C2 alkylthio, CpC2 alkylsulfinyl and C)-C2 alkylsullbnyl; one of the R4 groups is attached to the phenyl ring at the 2-position, and said R4 is CrC4 alkyl, C\|-C4 haloalkyl, halogen. CN, N02, C,-C4 alkoxy, CrC4 haloalkoxy, CpC4 alkylthio, C)-C4 alkylsulfinyl, C\|-C4 alkylsulfonyl, C[-C4 haloalkylthio, C\|-C4 haloalkylsulfinyl or C\|-C4 haloalkylsulfonyl; and each R7 is independently II, C\|-C4 alkyl, CrC4 haloalkyl, halogen, CN, N02, C\-C4 haloalkoxy, C\|-C4 alkylthio, C]-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, CrC^ haloalkylthio, CrC4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl or CVC4 alkoxycarbonyl; or a phenyl or a 5- or 6-membered heteroaromatic ring, each ring optionally substituted with CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, CrC4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, N02, CrC4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfmyl, CrC4 alkylsulfonyl, CrC4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C3-C6 (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl or C3-C6 trialkylsilyl. 30. The compound as claimed in 29 wherein J is selected from the group consisting of pyridine, pyrimidine, pyrazole, imidazole, triazole, thiophene, thiazole and oxazole, furan, isothiazole and isoxazole, each optionally substituted with 1 to 3 R'. 3 I. The compound as claimed in 30 wherein .1 is selected from the group consisting of pyridine, pyrimidine, pyrazole, thiophene and thiazole. each optionally substituted with 1 to 3 R7; R1 and R2 are both H; R3 is C\|-C4 alkyl optionally substituted with halogen, CN, OCH3, or S(0)pCH3; . each R4 is independently H, CH3, CF3, OCF3, OCHF2, S(0)pCF3, S(0)pCHF2, CN or halogen; each R7 is independently H, halogen, CH3, CF3. OCHF2, S(0)pCF3, S(0)pCHF2, OCH2CF3, OCF2CHF2, S(0)pCH2CF3, S(0)pCF2CHF2; or phenyl, pyrazole, imidazole, triazole, pyridine or pyrimidine. each ring optionally substituted with C,-C4 alkyl, C,-C4 haloalkyl, C,-C4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio. CrC4 alkylsulfmyl, Ct-C4 alkylsulfonyl, halogen orCN; and p is 0, 1 or 2. 32. The compound as claimed in 31 wherein J is a pyridine optionally substituted with 1 to 3 R7. 33. The compound as claimed in 32 wherein one R7 is a phenyl optionally substituted with C\|-C4 alkyl, CpC4 haloalkyl, halogen orCN. 34 The compound as claimed in 32 wherein one R7 is a pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted with Cj-C4 alkyl. C\|-C4 haloalkyl, halogen or CN. 35. The compound as claimed in 31 wherein J is a pyrimidine optionally substituted with 1 to 3 R7, 36. The compound as claimed in 35 wherein one R7 is a phenyl optionally substituted with Cj-C4 alkyl, CpC4 haloalkyl, halogen or CN. 37. The compound as claimed in 35 wherein one R7 is a r\zole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted with Ci-C4 alkyl, CrC4 haloalkyl, halogen or CN. 38. The compound as claimed in 31 wherein J is a pyrazole optionally substituted with 1 to 3 R7. 39. The compound as claimed in 38 wherein one R7 is a phenyl optionally substituted with Ci-C4 alkyl, C1-C4 haloalkyl, halogen or CN. 40. The compound as claimed in 38 wherein one R7 is a pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted with CpCj alkyl, C\|-C4 haloalkyl, halogen or CN. 41. The compound as claimed in 40 wherein wherein R7 is a pyridine optionally substituted with C1-C4 alkyl, C\|-C4 haloalkyl, halogen or CN. 42. The compound as claimed in 2Zselected from the group consisting of: 3-methyl-A'-(l-methylethyI)-2-[[4-(trifluoromethyl)benzoyl]amino]-benzamide, 2-mcthyl-A'-[2-methyl-6-[[(l-methylethyl)amino]carbonyl]phenyl]-4- (trifluoromethyl)benzamide-, 2-methyl-A'-[2-methyl-6-[[(l-methylethyl)amino]carbonyl]phenyl]-6-(trifluoromethyI)-3-pyridinecarboxamide, l-ethyl-A/-[2-methyl-6-[[(l-methylethyl)amino]carbonyl]phenyl]-3-(trifluoromethyl)-l//-pyrazole-5-carboxamide, 1 -(2-tluorophenyl)-A/-[2-methyl-6-[[( 1 -methylethyl)arnino)carbonyl]phenyl]-3- (trilluoromethyl)-l//-pyrazole-5-carboxaniide, 1 -(.Vchloro-2-pyridinyl)-Aq2-methyl-6-[[(1 - methylethyl)amino]carbonyl]phenyl]3-(trifluoromethyl)-l//-pyrazole-5- carboxamide. A'-f 2-chloro-6-[[( 1 -methylethy!)amino]carbonyl]phenyl]-1 -(3-chloro-2- pyridinyl)-3-(tritluoromethyl)-l//-pyrazole-5-carboxamide, J-bromo-1 -(2-chlorophenyl)-A/-[2-methyl-6-[[( 1 - methylethyl)amino]carbonyl]phenyl]-l/y-pyrazole-5-carboxamide. and 3-bromo-A'-[2-chloro-6-[[( 1 -methylethyl)amino]carbonyl]phenyl]-1 -(2- chlorophenyU-1//-pyrazole-S-carboxamide. 43. An arthropodicidal composition comprising an effective amount of a compound of formula 1. Dated this 27th day of August 2002 Archana Shanker Of Anand and Anand, Advocates Attorneys for the applicant

Full Text

FORM 2 .
THE PATENTS ACT 1970 [39 OF 1970]
COMPLETE SPECIFICATION
[See Section 10]
"INSECTICIDAL ANTHRANILAMIDES"

E.I. DU PONT DE NEMOURS AND COMPANY, a corporation organized and existing under the laws of the State of Delaware, of 1007 Market Street, Wilmington, Delaware 19898, United States of America,

The following specification particularly describes and ascertains the nature of the invention and the manner in which it is to be performed:-

WO 01/70671 PCT7US01/09338
TITLE
INSECTICIDAL ANTHRANILAMIDES BACKGROUND OF THE INVENTION This invention relates to certain anthranilamides, their iV-oxides, agriculturally 5 suitable salts and compositions, and methods of their use as arthropodicides in both agronomic and nonagronomic environments.
The control of arthropod pests is extremely important in achieving high crop
efficiency. Arthropod damage to growing and stored agronomic crops can cause significant
reduction in productivity and thereby result in increased costs to the consumer. The control
10 of arthropod pests in forestry, greenhouse crops, ornamentals, nursery crops, stored food and
fiber products, livestock, household, and public and animal health is also important. Many
products are commercially available for these purposes, but the need continues for new
compounds that are more effective, less costly, less toxic, environmentally safer or have
different modes of action.
15 NL 9202078 discloses 7V-acyl anthranilic acid derivatives of Formula i as insecticides

wherein, inter alia,
X is a direct bond;
20
SUMMARY OF THE INVENnON This invention pertains to a method for controlling arthropods comprising contacting 25 the arthropods or their environment with an arthropodicidally effective amount of a compound of Formula 1, its N-oxide or agriculturally suitable salts

WO 01/70671 PCT/US01/09338
wherein
A and B are independently 0 or S;
each J is independently a phenyl or naphthyl group substituted with 1 to 2 R5 and
5 optionally substituted with 1 to 3 R6;
or each J is independently a 5- or 6-membered heteroaromatic ring or an aromatic 8-,
9- or 10-membered fused heterobicyclic ring system wherein each ring or ring
system is optionally substituted with 1 to 4 R7;
n is 1 to 4;
10 RMsHjor alkyl, alkenyl, alkynylor cycloalkyl each
optionally substituted with one or more substituents selected from the group consisting of halogen, hydroxy, alkoxy, alkylthio,
alkylsulfinyl, alkylsulfonyl, alkoxycarbonyl, alkylamino,
dialkylamino and cycloalkylamino; or
15 R1 is alkylcarbonyl, alkoxycarbonyl, alkylaminocarbqnyl,
dialkylarninocarbonyl or R2isH, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy,
alkylamino, dialkylamino, C3-C6 cycloalkylamino, C2~C6
alkoxycarbonyl or alkylcarbonyl;
20 R3 is H; G; alkyl, alkenyl, alkynyl, cycloalkyl, each
optionally substituted with one or more substituents selected from the group consisting of halogen, G, CN, NO2, hydroxy, C1-C4 alkoxy, CyC^ haloalkoxy,
alkylthio, alkylsulfinyl, alkylsulfonyl,
alkoxycarbonyl, C2-C6 alkylcarbonyl, trialkylsilyl, or a phenyl, phenoxy
25 or 5- or 6-membered heteroaromatic ring, each ring optionally substituted with
one to three substituents independently selected from the group consisting of Cj-C4 alkyl, alkenyl, C2-C4 alkynyl,cycloalkyl, (VC4 haloalkyl, C2-
C4 haloalkenyl, haloalkynyl, C^-C^ halocycloalkyl, halogen, CN, NO2,
alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, alkylsulfinyl, C1-C4
30 alkylsulfonyl, alkylamino,dialkylamino, cycloalkylamino,

WO 01/70671 PCT/US01/09338
(alkyl)cycloalkylarnino, alkylcarbonyl, alkoxycarbonyl, C2-
Cg alkylarninocarbonyl, dialkylaminocarbonyl or trialkylsilyl; C.r
C4 alkoxy; alkylamino; dialkylamino; C3-Cg cycloalkylamino; C2-
Cg alkoxycarbonyl or C2-C6 alkylcarbonyl; or
5 R2 and R3 can be taken together with the nitrogen to which they are attached to form
a ring containing 2 to 6 atoms of carbon and optionally one additional atom of nitrogen, sulfur or oxygen, said ring may be optionally substituted with 1 to 4 substituents selected from the group consisting of C1-C2 alkyl, halogen, CN, N02 and CyC2 alkoxy;
10 G is a 5- or 6-membered nonaromatic carbocyclic or heterocyclic ring, optionally
including one or two ring members selected from the group consisting of C(=0), SO or S(0)2 and optionally substituted with 1 to 4 substituents selected from the group consisting of alkyl, halogen, CN, N02 and Cp^ alkoxy;
each R4 is independently H, CrC6 alkyl, C^-Cg alkenyl, C2-C6 alkynyl, C3-C6
15 cycloalkyl, CrC6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C6 .
halocycloalkyl, halogen, CN, N02, hydroxy, Cj-C/j. alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, CrC4 alkylsulfonyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, C2-C4 haloalkylsulfonyl, Cj-C^ alkylamino, C2-C8 oUalkylamino, C3-Cg cycloalkylamino, or C3-C6 trialkylsilyl; or
20 each R4 is independently phenyl, ben2yl or phenoxy,* each optionally substituted with
CrC4 alkyl, C2-C4 alkenyl, ilkynyl, C3-C6 cycloalkyl, CrC4 haloalkyl,
C2-C4 haloalkenyl, C2-C4 haloalkynyl, halocycloalkyl, halogen, CN,
N02, alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, 0^-
C4 alkylsulfonyl, C1-C4 alkylamino, dialkylamino, C3-C6
25 cycloalkylamino, C3-Cg (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-C6
alkoxycarbonyl, C2-C6 alkylarninocarbonyl, C3-Cg m'alkylaminocarbonyl or C3-Cg trialkylsilyl; each R5 is independently alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6
cycloalkyl, CrC6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C6
30 halocycloalkyl, halogen, CN, C02H, CONH2, N02, hydroxy, CrC6 alkoxy,
CrC6 haloalkoxy, CrC6 alkylthio, CrC6 alkylsulfinyl, CrCg alkylsulfonyl, Cj-Cg haloalkylthio, haloalkylsulfinyl, Ci-Cg haloalkylsulfonyl, C^Cg
alkylamino, C2-C12 dialkylamino, or C3-Cg cycloallcylarmno, C2-C6 alkylcarbonyl, C2-Cg alkoxycarbonyl, C2-Cg allcylaminocarbonyl, C3-Cg
35dialkylarninocarbonyl,trialkylsilyl; or
when attached to adjacent carbon atoms can be taken together as

WO 01/70671 PCT/US01/09338
each R6 is independently H, halogen, alkyl, alkenyL alkynyl, C3-
Cg cycloalkyl, alkoxy or alkoxycarbonyl; or
each R6 is independently a phenyl, benzyl, phenoxy, 5- or 6-membered
heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic
5 ring system, each ring optionally substituted with one to three substituents
independently selected from the group consisting of CVC4 alkyl, C2-C4 alkenyl,
C2-C4 alkynyl, C3-C6 cycloalkyl, CrC4 haloalkyl, C2-C4 haloalkenyl, C2-C4
haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, N02, Ci~C4 alkoxy, C^-C^
haloalkoxy, Cj-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4
10 altylamino, C2-Cg malkylatnino, C3-C6 cycloalkylamhio, C3-C6
(alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-Cg alkoxycarbonyl, C2-Cg alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl or C3-C6 trialkylsilyl; each R7 is independently alkenyl, alkynyl, C3-C6
cycloalkyl, Cj-Cg haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C6
15 halocycloalkyl, halogen, CN, C02H, CONH2,N02, hydroxy, CpC4 alkoxy,
CrC4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, CrC4 haloalkylthio, CrC4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, (VC4 alkylamino, C^-Cg dialkylamino, C3-Cg cycloalkylamino, C2-C6 alkylcarbonyl, C2-C6 alkoxycarbonyl, alkylaminocarbonyl,dialkylaminocarbonyl,
20 C3-C6 trialkylsilyl; or
each R7 is independently a phenyl, benzyl, benzoyl, phenoxy, 5- or 6-membered
heteroaromatic ring or an aromatic 8-, 9- or lOrmembered fused heterobicyclic
ring system, each ring optionally substituted with one to three substituents
independently selected from the group consisting of C1-C4 alkyl, C2-C4 alkenyl,
25 C2-C4 alkynyl, C3-C6 cycloalkyl, CrC4 haloalkyl, C^^ haloalkenyl, CVQ
haloalkynyl, C3-C6 halocycloalkyl, halogen, alkoxy, CrC4
haloalkoxy, CrC4 alkylthio, CVC4 alkylsulfinyl, CVC4 alkylsulfonyl, C1-C4
alkylamino, C2-Cg dialkylamino, C3-C6 cycloalkylamino, C3-C6
(alkyl)cycloallqdamino, C2-C4 alkylcarbonyl, C2-C^ alkoxycarbonyl, C2-C6
30 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl or C3-C6 trialkylsilyl;
provided that
(1) when A and B are both alkyL R3 is H or CrC3 alkyl and R4
is H, halogen, alkyl, phenyl, hydroxy or C^-Cg alkoxy, then one R5 is
other than halogen, C^Cg alkyl, hydroxy or C^-Cg alkoxy; or
35 (2) J is other than an optionally substituted 1,2,3-thiadiazole.
This invention also pertains to compounds of formula 1, their N-oxides and agriculturally suitable salts

WO 01/70671PCT/US01/09338
wherein
A and B are independently 0 or S;
each J is independently a phenyl or naphthyl group substituted with 1 to 2 R5 and [ ,
5 optionally substituted with 1 to 3 R6; ,
or each J is independently a 5- or 6-membered heteroaromatic ring or an aromatic 8-,
9- or 10-membered fused heterobicyclic ring system wherein each ring or ring
system is optionally substituted with 1 to 4 R7;
n is 1 to 4;
10 R]isH;or alkyl, alkenyl, C2-C6 alkynyl or C3-C6 cycloalkyl each
optionally substituted with one or more substituents selected from the group consisting of halogen, hydroxy, alkoxy, C\-C^ alkylthio, C1-C4
alkylsulfinyl, C\-C4 alkylsulfonyl, alkoxycarbonyl, C! -C4 alkylamino,
C2-Cg dialkylarnino and C3-Cg cycloalkylarnino; or
15 R1 is C2-Cg alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-Cg alkylarninocarbbnyl, C3-Cg
&altylaminocarbonyl or C(=A)J;
R2 is H, CrC6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, CrC4 alkoxy,
CyC$ alkylamino, C^-Cg dialkylarnino, C3-C6 cycloalkylarnino, C2-C6
alkoxycarbonyl or C^-Cg alkylcarbonyl;
20 R3 is H; CrC6 alkyl, C2-C6 alkenyl, C^-Cg alkynyl, C3-C6 cycloalkyl, each
optionally substituted with one or more substituents selected from the group
consisting of halogen, CN, N02, hydroxy, C1-C4 alkoxy, C1-C4 haloalkoxy, Cp
C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C2-Cg alkoxycarbonyl, .
C2-C6 alkylcarbonyl, C3-C5 trialkylsilyl, or a phenoxy ring optionally substituted
25 with one to three substituents independently selected from the group consisting
of CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, CrC4
haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl,
halogen, CN, N02, CrC4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio, CrC4
alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylamino, C2-Cs dialkylarnino, C3-
30 C6 cycloalkylarnino, C3-C6 (allqrl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-C6

WO 01/70671 PCT/US01/09338
alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl or C3-
Gg trialkylsttyl; 0^04 alkoxy, C1-C4 alkylamino; C2-Cg dialkylamino; C3-C6
cycloalkylamino; C2-Cg alkoxycarbonyl or C2-Cg alkylcarbonyl; or
R.2 and R3 can be taken together with the nitrogen to which they are attached to form
5 ■ a ring containing 2 to 6 atoms of carbon and optionally one additional atom of
nitrogen, sulfur or oxygen, said ring may be optionally substituted with 1 to 4 substiruents selected from the group consisting of Ci-C2 alkyl, halogen, CN, N02 and Cj-02 alkoxy; each R4 is independently H, C^Cg alkyl, C2-Cg alkenyl, C2-Cg alkynyl, C3-C6
10 cycloalkyl, CrC6 haloalkyl, C2-Cg haloalkenyl, C^-Cg haloalkynyl, C3-C6
halocycloalkyl, halogen, CN, N02, hydroxy, C1-C4 alkoxy, CJ-C4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, Ci-Q^ alkylsulfonyl, CrC4 haloalkylthio, CJ-C4 haloalkylsulfinyl, C^^ haloalkylsulfonyl, Q-C4 alkylamino, C2~C8 dialkylamino, C3-C6 cycloallcylamino, or C3-Cg trialkylsilyl; or
15 each R4 is independently phenyl, benzyl or phenoxy, each optionally substituted with
CrC4 alkyl, CVC4 alkenyl, C2-C4 alkynyl, C3-C6cycloalkyl, CrC4haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, N02, CrC4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, Cr C4 alkylsulfonyl, C1-C4 allcylamino, C2-C8 dialkylamino, C3-C6
20 cycloalkylamino, C3-Cg (alkyl)cyctoalkylamino, C2-C4 alkylcarbonyl, C2-C5
alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl or C3-C6 trialkylsilyl; each R5 is independently CrC6 haloalkyl, C2-C6 haloalkenyl, C2-Cg haloalkynyl, C3-Cg halocycloalkyl, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl,
25 CrC4 alkylsulfonyl, C!-C4 haloalkylthio, CrC4 haloalkylsulfinyl, CrC4
haloalkylsulfonyl, CN, N02, CrC4 alkoxycarbonyl, CJ-C4 alkylamino, C2-C8 dialkylamino, C3-Cg cycloallcylarnino, C^-Cg alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, or C3-Cg dialkylaminocarbonyl; or (R5)2 attached to adjacent carbon atoms can be taken together as -OCF20-,
30 -CF2CF20-, or -OCF2CF20-;
each R6 is independently H, halogen, Cj-Cg alkyl, C2-Cg alkenyl, C2-C6 alkynyl, C3-
C6 cycloalkyl, C1-C4 alkoxy or C2-C4 alkoxycarbonyl; or each R6 is independently a phenyl, benzyl, phenoxy, 5- or 6-membered
heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic
35 ring system, each ring optionally substituted with one to three substiruents
independently selected from the group consisting of C1-C4 alkyL C2-C4 alkenyl, C2~C4 alkynyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 , hai™iVvT.vi r~.r, haW.™inniVyi9 haloaen. CN.NOo. Cn-G. alkoxv. G-C
WO 01/70671 PCT/US01/09338
haloalkoxy, Ci-C4 alkylthio, CrC4 alkylsulfinyl, CrC4 alkylsulfonyl, CrC4
alkylamino, C2-Cg dialkylamino, C3-C6 cycloaUsylamino, C3-Cg
(alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-Cg alkoxycarbonyl, Cj-Cg
alkylarninocarbonyl, C3-C8 dialkylaminocarbonyl or C3-C6 trialkylsilyl;
5 each. R7 is independently H, CrC6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6
cycloalkyl, Cj-Cg haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C6
halocycloalkyl, halogen, CN, C02H, CONH2, N02, hydroxy, CrC4 alkoxy,
CrC4 haloalkoxy, CrC4 alkylthio, C1-C4 alkylsulfinyl, CrC4 alkylsulfonyl,
C1-C4 haloalkylthio, CrC4 haloalkylsulfinyl, CrC4 haloalkylsulfonyl, C1-C4
10 alkylamino, C2-Cg dialkylamino, C3-C6 cycloalkylarnino, C2-Cg alkylcarbonyl,
C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl,
C3-Cg trialkylsilyl; or
each R7 is independently a phenyl,.benzyl, benzoyl, phenoxy or 5- or 6-membered
■ heteroaromatic ring 8-, 9- or 10-membered fused heterobicyclic ring system,
15 each ring optionally substituted with one to three substituents independently
selected from the group consisting of C j -C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl,
C3-C6 cycloalkyl, CrC4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-
C6 halocycloalkyl, halogen, CN, N02, GrC4 alkoxy, CrC4 haloalkoxy, CrC4
alkylthio, Cj-C4 alkylsulfinyl, Ci-C4 alkylsulfonyl, C}-^ alkylamino, C^Cg
20 o^alkylarnino, C3-C6 cycloalkylamino, C3-C6 (alkyl)cycloalkylamino, C2-C4
alkylcarbonyl, C2-Cg alkoxycarbonyl, C^-Cg alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl or C3-Cg trialkylsilyl; provided that
(i) at least one R4 and at least one R7 are other than H;
25 (ii) J is other than an optionally substituted 1,2,3-thiadiazole;
(iii) when J is an optionally substituted pyridine and R2 is H, R3 is other than H or
CH3;
(iv) when J is an optionally substituted pyridine, then R7 cannot be CONH2, C2-C6
alkylaminocarbonyl or C3-Cg dialkylaminocarbonyl;
30 (v) when J is an optionally substituted pyrazole, tetrazole or pyrirnidine, then R2 and
R3 cannot both be hydrogen. This invention also pertains to arthropodicidal compositions comprising an arthropodicidally effective amount of a compound of Formula 1 and at least one additional component selected from the group consisting of surfactants, solid diluents and liquid 35 djhjgrtfs.
WO 01/70671 PCT/US01/09338
DETAILS OF THE INVENTION
In the above recitations, the term "alkyl", used either alone or in compound words such as "alkylthio" or "haloalkyl" includes straight-chain or branched alkyl, such as, methyl, ethyl, K-propyl, z-propyl, or the different butyl, pentyl or hexyl isomers. The term "1-2 5 alkyl" indicates that one or two of the available positions for that substituent may be alkyl. "Alkenyl" includes straight-chain or branched alkenes such as 1-propenyl, 2-propenyl, and the different butenyl, pentenyl and hexenyl isomers. "Alkenyl" also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. "Alkynyl" includes straight-chain or branched alkynes such as 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl
10 isomers. "Alkynyl" can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl "Alkoxy" includes, for example, methoxy, ethoxy, rc-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers. "Alkoxyalkyl" denotes alkoxy substitution on alkyl. Examples of "alkoxyalkyl" include CH3OCH2, CH3OCH2CH2, CH3CH2OCH2, CH3CH2CH2CH2OCH2 and CH3CH2OCH2CH2.
15 "Alkylthio" includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butyltbio, pentylthio and hexylthio isomers. "Cycloalkyl" includes, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
The term^'heterocycHc ring" or heterocyclic ring system" denotes rings or ring systems in which at least one ring atom is not carbon and comprises 1 to 4 heteroatoms
20 independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that each heterocyclic ring contains no more than 4 nitrogens, no more than 2 oxygens and no more than 2 sulfurs. The heterocyclic ring can be attached through any available carbon or nitrogen by replacement of hydrogen on said carbon or nitrogen. The term "aromatic ring system" denotes fully unsaturated carbocycles and heterocycles in which the polycyclic ring
25 system is aromatic (where aromatic indicates that the Hiickel rule is satisfied for the ring system). The term "heteroaromatic ring" denotes fully aromatic rings in which at least one ring atom is not carbon and comprises 1 to 4 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that each heterocyclic ring contains no more than 4 nitrogens, no more than 2 oxygens and no more than 2 sulfurs
30 (where aromatic indicates that the Htickel rule is satisfied). The heterocyclic ring can be attached through any available carbon or nitrogen by replacement of hydrogen on said carbon or nitrogen. The term "aromatic heterocyclic ring system" includes fully aromatic heterocycles and heterocycles in which at least one ring of a polycyclic ring system is aromatic (where aromatic indicates that the Hiickel rule is satisfied). The term "fused
35 heterobicyclic ring system" includes a ring system comprised of two fused rings in which at

one ring atom is not carbon and can be aromatic or non aromatic, as defined above. The term "halogen", either alone or in compound words such as "haloalkyl", includes when used in cnm-nound words such as

WO 01/70671 PCT/US01/09338
"haloalkyl", said alkyl may be partially or fully substituted with halogen atoms which may be the same'or different. Examples of "haloalkyl" include F3C, CICH2, CF3CH2 and CF3CC12. The terms "haloalkenyl", "haloalkynyl", "haloalkoxy", and the like, are defined analogously to the term "haloalkyl". Examples of "haloalkenyl" include (C1)20=CHCH2 5 and CF3 CH2CH=CHCH2. Examples of "haloalkynyl" include HCsCCHCL CF3OC, CCI3OC and FCH2OCCH2. Examples of "haloalkoxy" include CF30, CC13CH20, HCF2CH2CH20 and CF3CH20.
The total number of carbon atoms in a substituent group is indicated by the "Ci-Cj" prefix where i and j are numbers from 1 to 6. For example, CyC^ alkylsulfonyl designates
10 methylsulfonyl through propylsulfonyl; C2 alkoxyalkyl designates CH3OCH2; C3
alkoxyalkyl designates, for example, CH3CH(OCH3), CH3OCH2CH2 or CH3CH2OCH2; and C4 alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH3CH2CH2OCH2 and CH3CH2OCH2CH2. In the above recitations, when a compound of
15 Formula 1 contains a heterocyclic ring, all substituents are attached to this ring through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.
When a group contains a substituent which can be hydrogen, for example R3, then, when this substituent is taken as hydrogen, it is recognized that this is equivalent to said group being unsubstituted.
20 - • Compounds of this invention can exist as one or more stereoisomers. The various
stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers. One skilled in the art will appreciate that one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). Additionally, the skilled artisan knows how to
25 separate, enrich, and/or to selectively prepare said stereoisomers. Accordingly, the compounds of the invention may be present as a mixture of stereoisomers, individual stereoisomers, or as an optically active form.
The present invention comprises compounds selected from Formula 1, JV-oxides and agriculturally suitable salts thereof. One skilled in the art will appreciate that not all nitrogen
30 containing heterocycles can form iV-oxides since the nitrogen requires an available lone pair for oxidation to the oxide; one skilled in the art will recognize those nitrogen containing heterocycles which can form TV-oxides. One skilled in the art will also recognize that tertiary amines can form N-oxides. Synthetic methods for the preparation of iV-oxides of heterocycles and tertiary amines are very well known by one skilled in the art including the
35 oxidation of heterocycles and tertiary amines with peroxy acids such as peracetic and ffz-chloroperbenzoic acid (MCPB A), hydrogen peroxide, alkyl hydroperoxides such as f-butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethydioxirane. These methods fnr the nrp.nnration nf W-nviHp.5 havp been extensivelv described and reviewed in the
WO 01/70671 PCTAJS01/09338
literature, see for example: T. L. Gilchrist in Comprehensive Organic Synthesis, vol. 7,
pp 748-750, £>. V. Ley, Ed, Pergamon Press; M. Tisler and B. Stanovnik in Comprehensive
Heterocyclic Chemistry, vol. 3, pp 18-19, A. J. Boulton and A. McKiHop, Eds., Pergamon
Press; M. R. Grirnmett and B. R. T. Keene in Advances in Heterocyclic Chemistry, vol. 43,
5 pp 139-151, A. R. Katritzky, Ed., Academic Press; M. Tisler and B. Stanovnik in Advances
in Heterocyclic Chemistry, vol. 9, pp 285-291, A. R. Katritzky and A. J. Boulton, Eds.,
Academic Press; and G. W. H. Cheeseman and E. S. G. Wersriuk in Advances in
Heterocyclic Chemistry, vol. 22, pp 390-392, A. R. Katritzky and A. J. Boulton, Eds.,'
Academic Press.
10 The salts of the compounds of the invention include acid-addition salts with
inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, furnaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids.
Of note are certain compounds of Formula II
15
wherein
XandYareO;
m is 1 to 5;
n is 1 to 4;
20 R1 is H; or CrC6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or C3-C6 cycloalkyl each
optionally substituted with one or more substituents selected from the group
consisting of halogen, CN, NO2, hydroxy, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4
alkylsulfinyl, CrC4 alkylsulfonyl, C2-C4 alkoxycarbonyl, C1-C4 alkylarnino,
C2-Cg dialkylamino and C3-C6 cycloalkylamino; or
25 R1 is C2-Cg alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl or
C3-Cg dialkylaminocarbonyl;
WO 01/70671 PCT/US01/09338
R2 is H, CrC6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, CrC4 alkoxy,
CrC4 aUcylamino, C2~Cg dialkylamino, C3-C alkoxycarbonyl or C2-C6 alkylcarbonyl;
R3 is z-propyl or ?-butyl; and
5 each R4 and R5 are independently H, Ci~C6 alkyl, C2-Q alkenyl, C2-Cg alkynyl,
C3-C6 cycloalkyl, Cj-Cg haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl,
CrC6 halocycloalkyl, halogen, CN, C02H, CONH2, N02, hydroxy, CrC4
alkoxy, C^-04 haloalkoxy, Cj-04 alkylthio, Q-C4 alkylsuLfinyl, Ct-C4
alkylsulfonyl, CJ-C4 haloalkylthio, Cj-C4 haloalkylsulfinyl, C1-C4
10 haloalkylsulfonyl, CrC4 alkoxycarbonyl, C1-C4 alkylamino, C2-C§
diallcylamino, C3-Cg cycloalkylamino, C2-Cg alkylcarbonyl, C2-C5
alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-Cg dialkylarainocarbonyl, C3-C6
trialkylsilyl; or - ■
each R4 and R5 are independently phenyl optionally substituted with CpC4 alkyl,
15 Qrc4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, CrC4 haolalkyl, C2-C4
haloalkenyl, C2-C4 haloalkynyl, C3-Cg halocycloalkyl, halogen, CN, N02,
CrC4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, CrC4
alkylsulfonyl C]-C4 alkoxycarbonyl, (VC4 alkylamino, C2-C8 dialkylamino,
C3-Cg cycloalkylamino, C3-C6 (alkyl)cycloalkylarnino, C2-C4 alkylcarbonyl,
20 C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-Cg dialkylaroinocarbonyl
or C3-Cg trialkylsilyl.
Also of note are methods for controlling arthropods comprising contacting the
arthropods or their environment with an arthropodicidally effective amount of a compound
of Formula II and insecticidal compositions thereof.
25 Also of note are certain compounds of Formula m

wherein
A and B are independently 0 or S;
WO 01/70671 PCT/US01/09338
J is a phenyl group substituted with 1 to 2 R5 and optionally substituted ■with 1 to 3 R6, or a 5- or 6-membered heteroaromatic ring optionally substituted with 1 to 4 R7;
n is 1 to 4;
5 R1 is H; or CrC6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or C3-C6 cycloalkyl each
optionally substituted with one or more substituents selected from the group consisting of halogen, CN, N02, hydroxy, Cj-C4 alkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, Ci-C4 alkylsulfonyl, C2-C4 alkoxycarbonyl, C1-C4 alkylarnino, C2-Cg dialkylamino and C3-Cg cycloaU^lamino; or
10 R1 is C2-C6 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylarninocarbonyl or
C3-Cg dialkylaminocarbonyl; R2 is H, CrC6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, CrC4 alkoxy, CJ-C4 alkylarnino, C2-Cg dialkylamino, C3-C6 cycloalkylamino, Qj-Cg alkoxycarbonyl or C^-Cg alkylcarbonyl;
15 R3 is H; or CrC6 alkyl, C2-C6 alkenyl, C2~C6 alkynyl or C3-C6 cycloalkyl each
optionally substituted with one or more substituents selected from the group consisting of halogen, CN, N02, hydroxy, (VC4 alkoxy, (VC4 alkylthio, C1-C4 alkylsulfinyl and CyC^ alkylsulfonyl; or R2 and R3 can be taken together with the nitrogen to which they are attached to form
20 a ring containing 2 to 6 atoms of carbon and optionally one additional atom of
nitrogen, sulfur or oxygen, said ring may be optionally substituted with 1 to 4 substituents selected from the group consisting of Ci~C2 alkyl, halogen, CN, N02 and Cj-C^ alkoxy; each R4 is independently H, Cj-Cg, alkyl, C2-C5 alkenyl, C2-Cg alkynyl, C3-Cg
25 cycloalkyl, CrC6 haloalkyl, C^-Cg haloalkenyl, C2-C6 haloalkynyl, C3-C6
halocycloalkyl, halogen, CN, C02H, CONH2,N02, hydroxy, CrC4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, Cj-C4 alkylsulfinyl, C^-C4 alkylsulfonyl, C!-C4 haloalkylthio, C!-C4 haloalkylsulfinyl, C!-C4 haloalkylsulfonyl, CrC4 alkylarnino, C2-C8 dialkylamino, C3-C6 cycloallcylamino, C2-C6 alkylcarbonyl,
30 C2-Cg alkoxycarbonyl, C2-Cg alkylarninocarbonyl, C3-Cg dialkylaminocarbonyl,
C3-C6 trialkylsilyl; or each R4 is independently phenyl, benzyl or phenoxy, each optionally substituted with CrC4 alkyl, CrC4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, CrC4 haolalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN,
35 N02, CJ-C4 alkoxy, CrC4haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl,
C!-C4 alkylsulfonyl, C1-C4 alkylarnino, C2-Cg dialkylamino, C3-C6 cycloalkylamino, C3-C6 (alkyl)cycloalky]amrno, C2-C4 alkylcarbonyl, C^-Cg

WO 01/70671 PCT/US01/09338
alkoxycarbonyl, Cj-C^ alkylaminocarbonyl, C3-Cg diallcylaminocarbonyl or
C3-C6 trialkylsilyl;
each R5 is independently Cj-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl,
C3-Cg halocycloalkyl, CrC4 haloalkoxy, CrC4 alkyltbio, CrC4 alkylsulfinyl,
5 crc4 alkylsulfonyl, CrC4 haloalkylthio, CrC4 haloalkylsulfinyl.. CrC4
haloalkylsnlfonyl, CN, N02, CrC4 alkylamino, C2-Cs dialkylamino, C3-C6 cycloalkylamino, C2-Cg alkylcarbonyl, C2-C6 alkoxycarbonyl, C^-Cg alkylaminocarbonyl, or C3-Cg dialkylaminocarbonyl; or (R5)2 when attached to adjacent carbon atoms can be taken together as -OCF20-,
10 -CF2CF20-5 or -OCF2CF20-;
each R6 is independently H, halogen, CpCg alkyl, C2-C6 alkenyl, C2-Cs alkynyl, C3-
Cg cycloalkyl, Ci~C4 alkoxy; or -
each R6 is independently phenyl, benzyl or phenoxy, each optionally substituted with CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, CrC4 haolalkyl,
15 C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN,
N02, CrC4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, Cr C4 alkylsulfonyl, Cj-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C3-Cg (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alfylaminocarbonyl, C3-C8 dialkylaminocarbonyl or C3-
20 C6 trialkylsilyl;
each R7 is independently H, Cj-C6 alkyl, Cj-Cg alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, CrC6 haloalkyl, C2-Cg haloalkenyl, C2-C6 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, C02H, CONH2, N02, hydroxy, CrC4 alkoxy, Cj-04 haloalkoxy, Cj-C4 alkylthio, Cj-C4 alkylsulfinyl, C1-C4 alkylsulfonyl,
25 CrC4 haloalkylthio, CrC4 haloalkylsulfinyl, CrC4 haloalkylsulfonyl, CrC4
alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkylcarbonyl, C2-Cg alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl, C3-Cg trialkylsilyl; or each R? is independently phenyl, benzyl or phenoxy, each optionally substituted with
30 CrC4 alkyl, C2-C4 alkenyl, CrC4 alkynyl, C3-C6 cycloalkyl, CrC4 haloalkyl,
C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-Cg halocycloalkyl, halogen, CN, N02, CrC4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, Cr C4 alkylsulfonyl Cj^ alkoxycarbonyl, C}-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C3-C6 (alkyl)cycloallqrtamino, C2-C4 alkylcarbonyl,
35 C2-Cg alkoxycarbonyl, C2-Cg alkylaminocarbonyl, C3-C3 dialkylaminocarbonyl
or C3-Cg trialkylsilyl.

WO 01/70671 PCT/US01/09338
Also of note are methods for controlling arthropods comprising contacting the arthropods or their environment with an arthropodicidally effective amount of a compound of Formula IE and insecticidal compositions thereof.
Also of note are certain compounds of Formula IV
5
wherein
A and B are independently O or S;
J is a phenyl group substituted with 1 to 2 R5, and optionally substituted with 1 to 3
R6, or a 5- or 6-membered heteroaromatic ring optionally substituted with 1 to 4
10 R7;
n is 1 to 4;
R1 is H; or CVCs alkyl, C2-Cg alkenyl, C2-C6 alkynyl or C3-C6 cycloalkyl each
optionally substituted with one or more substituents selected from the group
consisting of halogen, CN, N02, hydroxy, C1-C4 alkoxy, C1-C4 alkylthio, Q-C4
15 alkylsulfinyl, C1-C4 alkylsulfonyl, Q2-C4 alkoxycarbonyl, C1-C4 alkylamino,
C2-Cg a^alkylarnino and C3-C6 cycloalkylamino; or R1 is C2-Cg alkylcarbonyl, C^-Cg alkoxycarbonyl, C2-Cg alkylaminocarbonyl or
C3-Cg dialkylaminocarbonyl;
R2 is H, CrC6 alkyl, C2-C6 alkenyl, CrC6 alkynyl, C3-C6 cycloalkyl, CrC4 alkoxy,
20 C1-C4 alkylamino, C2-Cg dialkylamino, CyCg cycloaU^lamino, C2-C6
alkoxycarbonyl or C2-Cg alkylcarbonyl;
R3 is H; CrC6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, each
optionally substituted with one or more substituents selected from the group
consisting of halogen, CN, N02, hydroxy, CVC4 alkoxy, C1-C4 alkylthio, C1-C4
25 alkylsulfinyl and C1-C4 alkylsulfonyl; C1-C4 alkoxy; Ci-C4'alkylamino; C2-Cg
dialkylamino; C3-C6 cycloalkylamino; C2-Cg alkoxycarbonyl or C2-Cg
alkylcarbonyl; or
R2 and R3 can be taken together with the nitrogen to which they are attached to form
a ring containing 2 to 6 atoms of carbon and optionally one additional atom of
30 nitrogen sulfur r\r nwop.n said ring may be optionally substituted with 1 to 4
WO 01/70671 PCT7US01/09338
substituents selected from the group consisting of C1-C2 alkyl, halogen, CN,
NO2 and C1-C2 alkoxy;
each R4 is independently H, CrC6 alkyl, C^-Cg alkenyl, C2-C6 alkynyl, C3-C6
cycloalkyl, CpCg haloalkyl, C2-C6 haloalkenyl, C2-Cg haloalkynyl, C3-C6
5 halocycloalkyl, halogen, CN, C02H, CONH2, N02, hydroxy, CrC4 alkoxy,
CrC4 haloalkoxy, C1-C4 alkylthio, C]^ alkylsulfinyl, CrC4 alkylsulfonyl, CrC4 haloalkylthio, CrC4haloalkylsulfinyl, C1-C4haloalkylsulfonyl, Cj-Q alkylarnino, C2-C8 dialkylamino, C3-Cg cycloalkylamino, C2-C6 alkylcarbonyl, C2-Cg alkoxycarbonyl, C2-Cg alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl,
10 C3-Ce trialkylsilyl; or
each R4 is independently phenyl, benzyl or phenoxy, each optionally substituted with CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, CrC4 haolalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, N02, Cj-C4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, Cr
15 C4 alkylsulfonyl, Ci-C4 alkylarnino, C2-Cs dialkylamino, C3-Cg
cycloalkylarniiio, C3-Cg (allcyl)cycloalkylarrihio, C2-C4 alkylcarbonyl, C2-Cg , alkoxycarbonyl, C2-Cg altylaminocarbonyl, C3-C8 dialkylaminocarbonyl or C3-C6 trialkylsilyl; each R5 is independently Cj-Cg alkyl, Q2-C6 alkenyl C2-Cg alkynyl, C3-Cg
20 cycloalkyl, CrC6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C6
halocycloalkyl, halogen, CN, C02H, CONH2, N02, hydroxy, CrC4 alkoxy, CyC^ haloalkoxy, CrC4 alkylthio, CX-C4 alkylsulfinyl, Cj-C4 alkylsulfonyl, Ci-C4 haloalkylthio, CrC4 haloalkylsulfinyl, C2-C4 haloalkylsulfonyl, Ci-C4 alkylarnino, C2-C8 dialkylarnino, C3-Cg cycloalkylamino, GrCg alkylcarbonyl,
25 C2-Cg alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8 diaHcylarninocarbonyl,
C3-Cg trialkylsilyl; or (R5)2 when attached to adjacent carbon atoms can be taken together as -0CF2O,
-CF2CF20-r or-OCF2CF20-; each R6 is independently H, halogen, Cj-Cg alkyl, C2-Cg alkenyl, C2-C6 alkynyl, C3-
30 C6 cycloalkyl, C1-C4 alkoxy; or
each R6 is independently a phenyl, benzyl, phenoxy or a 5- or 6-membered
heteroaromatic ring, each ring optionally substituted with C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-Cg cycloalkyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, N02, Ci-C4 alkoxy, Cr
35 C4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, CrC4 alkylsulfonyl, CrC4
alkylarnino, C2-Cg dialkylamino, C3-Cg cycloall^lamino, C3-Cg (alkyl)cycloalkylamino, Q2-C4 alkylcarbonyl, C^Cg alkoxycarbonyl, C2-Cg niVviflTTiJinnr^rKnnvi n^n„ /«aii^iarninocarbonvl or Ci-C* trialkvlsilvl:
WO 01/70671 PCT/US01/09338
each R7 is independently H, C1-C6 alkyl, C2-Cg alkenyl, C2-Cg alkynyl, C3-C6
cycloalkyl, Cj-Cg haloalkyl, C2-Cg haloalkenyl C2-Cg haloalkynyl, C3-Cg
halocycloalkyLhaiogen, CN, C02H, CONH2, N02, hydroxy, CrC4 alkoxy,
Cj-C4 haloalkoxy, CrC4 alkylthio, C^-Q alkylsulfinyl, C1-C4 alkylsulfonyl,
5 crc4 haloalkylthio, CrC4 haloalkylsulfinyl, CrC4 haloalkylsulfonyl, Cx-C^.
aLkylamhio, C2-C8 dialkylamino, C3-Cg cycloalkylamino, C2-Cg alkylcarbonyl,
C2-Cg alkoxycarbonyl, C2-Cg alkylarninocarbonyl, C3-C8 dialkylaminocarbonyl.,
C3-C6 trialkylsilyl; or
each R7 is independently a phenyl, benzyl, benzoyl, phenoxy or a 5- or 6-membered
10 heteroaromatic ring, each ring optionally substituted with C]-C4 alkyl, C2-C4
alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, Cj-C4 haolalkyl, C2-C4 haloalkenyl,
C2-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, N02, C!-C4 alkoxy, Cr
C4 haloalkoxy, Ci-C4 alkylthio, C1-C4 alkylsulfinyl, Ci-C4 alkylsulfonyl, CrC4
alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C3-Cg
15 (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C^-Cg alkoxycarbonyl, C2-Cg
alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl or C3-Cg trialk>rlsilyl;
provided that when A and B are both 0, R2 is H or C]_-C3 alkyl, R3 is H or C|-C3
alkyl and R4 is H, halogen, CrC6 alkyl, phenyl, hydroxy or Ci-C6 alkoxy, then
one R5 is other than halogen, C^Cg alkyl, hydroxy or Cj-Cg alkoxy.
20 Also of note are methods for controlling arthropods comprising contacting the
arthropods or their environment with an arthropodicidally effective amount of a compound of Formula IV and insecticidal compositions thereof.
Preferred methods for reasons of better activity are:
Preferred 1. Methods comprising compounds of Formula 1 wherein J is a phenyl
25 group substituted with 1 to 2 R5 and optionally substituted with 1 to 3 R6.
Preferred 2. Methods of Preferred 1 wherein
A and B are both O;
n is 1 to 2;
R1 is H, CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, CrC6 cycloalkyl, C2-C6
30 alkylcarbonyl or C2-C6 alkoxycarbonyl;
R2 is H, CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C2-C6
alkylcarbonyl or C2-Cg alkoxycarbonyl;
R3 is Cj-Cg alkyl, Qj-Cg alkenyl, C2-Cg alkynyl or C3-C6 cycloalkyl each optionally
substituted with one or more substituents selected from the group
35 consisting of halogen, CN, Cj^ alkoxy, Cj-C^ alkylthio, C^^
alkylsulfinyl and Ci-C2 alkylsulfonyl; one of the R4 groups is attached to the phenyl ring at the 2-position or 5-position, and said T?4 is C.,-r. WO 01/70671 PCT/US01/09338
alkoxy, CyC^. haloalkoxy, CyC^ alkylthio, C1-C4 alkylsulfinyl, CyC4
alkylsulfonyl, CyC$ haloalkylthio, CyC^ haloalkylsulfinyl or C1-C4
haloalkylsulfonyl;
each R5 is independently C1-C4 haloalkyl, GN, N02, CrC4 haloalkoxy, C}-^
5 alkylthio, CrC4 alkylsulfinyl, CrC4 alkylsulfonyl, CrC4
haloalkylthio, CrC4 haloalkylsulfinyl, CrC4 haloalkylsulfonyl or C2-
C4 alkoxycarbonyl; or
(R5)2 when attached to adjacent carbon atoms can be taken together as -OCF20-,
-CF2CF20- or -OCF2CF20-; and
10 each R6 is independently H, halogen, CrC4 alkyl, CrC2 alkoxy or C?-C4
alkoxycarbonyl, or
each R6 is independently a phenyl or a 5- or 6-membered heteroaromatic ring, each
ring optionally substituted with CrC4 alkyl, C2-C4 alkenyl, C2-C4
alkynyl, C3~C6 cycloalkyl, CrC4 haloalkyl, C2-C4 haloalkenyl, C2~C4
15 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN,N02, CrC4 alkoxy,
C2-C4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, CrCA
alkylsulfonyl, CyC4 alkylamino, C2-C8 dialkylamino, C3-C6
cycloalkylamino, C3-C6 (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl,
C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8
20 dialkylaminocarbonyl or C3-C6 trialkylsilyl.
Preferred 3. Methods of Preferred 2 wherein R1 and R2 are both H;
R3 is CrC4 alkyl optionally substituted with halogen, CN, OCH3, S(0)pCH3;
each R4 is independently H, CH3, CF3i OCF3, OCHF2, S(0)pCF3, S(0)pCHF2, CN
25 or halogen;
eachR5 is independently CF3, OCF3> OCHF2, S(0)pCF3, S(0)pCHF2, OCH2CF3,
OCF2CHF2, S(0)pCH2CF3 or S(0)pCF2CHF2; each R6 is independently H, halogen or methyl; or phenyl, pyrazole, imidazole,
triazole, pyridine or pyrimidine, each ring optionally substituted with
30 CrC4 alkyl, CrC4 haloalkyl, halogen or CN; and
p is 0,1 or 2.
Preferred 4. Methods of Preferred 3 wherein R3 is z-propyl or f-butyl.
Preferred 5. Methods comprising compounds of Formula 1 wherein J is a 5- or 6-
membered heteroaromatic ring optionally substituted with 1 to 4 R7.
35 Preferred 6. Methods of Preferred 5 wherein
J is a 5- or 6-membered heteroaromatic ring selected from the group consisting of J-1, J-2, J-3, J-4 and J-5, each J optionally substituted with 1 to 3 R7
WO 01/70671 PCT/US01/09338

QisO, SorNR7;and
W, X, Y and Z axe independently N or CR7, provided that in J-4 and J-5 at
least one of W, X, Y or Z is N.
5 Preferred 7. Methods of Preferred 5 or Preferred 6 wherein
A and B are O;
n is 1 to 2;
R1 is H, CrC4 alkyL C2-C4 alkenyl, C2-C4 alkynyl, C2-C6 alkylcarbonyl or
C2-Cg alkoxycarbonyl;
10 R2 is H, CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C2-C6
alkylcarbonyl or C^-Cg alkoxycarbonyl;
R3 is H; or C^Cg alkyl, C2-C6 alkenyl, C2-C6 alkynyl or C3-C6 cycloalkyl
each optionally substituted with one or more substituents selected from
the group consisting of halogen, CN, C^-C^ alkoxy, C1-C2 alkylthio,
15 . CrG2 alkylsulfinyl and CrC2 alkylsulfonyl;
one of the R4 groups is attached to the phenyl ring at the 2-position, and said
R4 is CrC4 alkyl, CrC4 haloalkyl, halogen, CN, N02, C x -C4 alkoxy,
CrC4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, CVC4
alkylsulfonyl, CrC4 haloalkylthio, C}^ haloalkylsulfinyl, or C1-C4
20 haloalkylsulfonyl; and
each R7 is independently H, Cj-C4 alkyl, C2-C4 haloalkyl, halogen, CN, N02,
CrC4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, CrC4
alkylsulfonyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, Ci-C4
haloalkylsulfonyl or C2-C4 alkoxycarbonyl; or a phenyl or a 5- or
25 6-membered heteroaromatic ring, each ring optionally substituted with
CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl C3-C6 cycloalkyl, CrC4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-Cg halocycloalkyl, halogen, CN, N(>2, Ci~C4 alkoxy, Cj-C4 haloalkoxy, CrC4 alkylthio, r.-r. niwi«iifiTwi r._c4 alkvlsulfonvL Ci-C alkvlarnino. C-C»
WO 01/70671 PCT/USQ1/09338
cUalkylamino, C3-C6 cycloalkylamino, C3-C6 (alkyl)cycloaIkylamino,
C2-C4 atkylcarbonyl, ^-Cg alkoxycarbonyl, C^-Cs
alkylaininocarbonyl, C3-Cg dialkylaminocarbonyl or C3-C6 trialkylsilyl.
Preferred 8. Methods of Preferred 7 wherein
5 J is selected from the group consisting of pyridine, pyrirnidine, pyrazole,
imidazole, triazole, thiophene, tbiazole and oxazole, furan, isothiazole and isoxazole, each optionally substituted with 1 to 3 R7. Preferred 9. Methods of Preferred 8 wherein
J is selected from the group consisting of pyridine, pyrirnidine, pyrazole,
10 thiophene and thiazole, each optionally substituted with 1 to 3 R7;
R1 and R2 are both H;
R3 is CrC4 alkyl optionally substituted with halogen, CN, OCH3, S(0)pCH3;
each R4 is independently H, CH3, CF3, OCF3, OCHF2, S(0)pCF3,
S(0)pCHF2, CN or halogen;
15 each R7 is independently H, halogen, CH3, CF3, OCHF2, S(0)pCF3,
S(0)pCHF25 OCH2CF3, OCF2CHF2, S(0)pCH2CF3, S(0)pCF2CHF2;
or phenyl, pyrazole, imidazole, triazole, pyridine or pyrirnidine, each
ring optionally substituted with CVC4 alkyl, C1-C4 haloalkyl, C1-C4
alkoxy, CrC4 haloalkoxy, CrC4 alkylthio, C1-C4 alkylsulfinyl, CrC4
20 alkylsulfonyl, halogen or CN; and
p is 0,1 or 2. Preferred 10. Methods of Preferred 9 wherein J is a pyridine optionally substituted with
1 to 3 R7.
Preferred 11. Methods of Preferred 10 wherein one R7 is a phenyl optionally substituted
25 with CrC4 alkyl, CrC4 haloalkyl, halogen or CN.
Preferred 12. Methods of Preferred 10 wherein one R7 is a pyrazole, imidazole, triazole,
pyridine or pyrirnidine, each ring optionally substituted with Cj-C4 alkyl, C1-C4
haloalkyl, halogen or CN.
Preferred 13. Methods of Preferred 9 wherein J is a pyrirnidine optionally substituted
30 with 1 to 3 R7.
Preferred 14. Methods of Preferred 13 wherein one R7 is a phenyl optionally substituted
with C!-C4 alkyl, C1-C4 haloalkyl, halogen or CN.
Preferred 15. Methods of Preferred 13 wherein one R7 is a pyrazole, imidazole, triazole,
pyridine or pyrirnidine, each ring optionally substituted with C1-C4 alkyl, C1-C4
35 haloalkyl, halogen or CN.
Preferred 16. Methods of Preferred 9 wherein J is a pyrazole optionally substituted with 1 to 3 R7.
WO 01/70671 PCT/US01/09338
Preferred 17. Methods of Preferred 16 wherein one R7 is a phenyl optionally substituted
with Ci-C4 alkyl, CrC4 haloalkyl, halogen or CN.
Preferred 18. Methods of Preferred 16 wherein one R7 is a pyrazole, imidazole, triazole,
pyridine or pyrirnidine, each ring optionally substituted with CVC4 alkyl, CrC4
5 haloalkyl, halogen or CN.
Preferred 19. Methods of Preferred 18 wherein R7 is a pyridine optionally substituted
with C] -C4 alkyl, Cj -C4 haloalkyl, halogen or CN.
Most preferred is the method comprising a compound of Formula 1 selected from the
group consisting of:
10 3-methyl-iV-(l -me&ylethyl)-2-[[4-(trifluorome
2-memyl-A^-[2-memyl-6-[[(l-memylemyl)amino]carbonyl]phenyl]-4-(trifluoromethyl)benzamide,
2-me1hyl-iV-[2-memyl-6-[[(l-memylemyl)anuno]carbonyl]phenyl]-6-
(trifluoromemyl)-3-pyridinecarboxamide,
15 1 -ethyl-JV-[2-methyl-6-[[(l -memylemyl)arnino]carbonyl]phenyl]-3-
(trifluoromethyl)- li7-pyrazole-5-carboxamide,
l-(2-fluorophenyl)-iV-[2-memyl^-[[(l-memylemyl)amino)carbonyl]phenyl]-3-
(trifluoromethyl)-l^f-pyrazoler5-carboxarnide,
l-(3^hloro-2-pyria^yl)-iV'-[2-memyl-64^
20 (trifluoromethyl)- lif-pyra2ole-5-carboxamide,
JN^[2-cmoro-6-[[(l-memylemyl)arrdno]carbonyl]phenyl]-l-(3-chloro-2-pyridinyl)-3--
(trifluoromemyl)-liif-pyrazole-5-carboxamide,
5-bromo-l-(2-chlorophenyl)-A'-[2-methyl-6-[[(l-
memylemyl)amino]carbonyl]phenyl]- l^T-pyrazole-5-carboxamide, and
25 3-bromo-iV'-[2-cWoro-6-[[(l-memylemyl)aminoJcarbonyl]phenyl]-l-(2-
cMorophenyl)-li?-pyrazole-5-carboxamide.
Preferred compounds for reasons of better activity and/or ease of synthesis are:
Preferred A. Compounds of Formula 1 wherein J is a phenyl group substituted with 1 to
2 R5 and optionally substituted with 1 to 3 R6..
30 Preferred B. Compounds of Preferred A wherein
A and B are both 0; n is 1 to 2;
Rl is H, CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C2-C6 .
alkylcarbonyl or C2-C6 alkoxycarbonyl;
35 R2 is H, CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C2-C6
alkylcarbonyl or C^-Cg alkoxycarbonyl; R3 is CrC6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or C3-C6 cycloalkyl each with one or more substituents selected from the
WO 01/70671 PCT/US01/09338
group consisting of halogen, CN, C1-C2 alkoxy, C1-C2 alkylthio, Ci~C2
alkylsulfinyl and C1-C2 alkylsulfonyl;
one of the R4 groups is attached to the phenyl ring at the 2-position. or 5-
position, and said R4 is C1-C4 alkyl, C1-C4 haloalkyl, halogen, CN,
5 N02, C!-C4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio, CrC4
alkylsulfinyl, C1-C4 alkylsulfonyl, CrC4 haloalkylthio, CrC4
haloalkylsulfinyl or C!-C4 haloalkylsulfonyl;
each R5 is independently C1-C4 haloalkyl, CN, NO2, C1-C4 haloalkoxy, Cr
C4 alkylthio, CrC4 alkylsulfinyl, C]-C4 alkylsulfonyl, CrC4
10 haloalkylthio, C1-C4 haloalkylsulfinyl, CrC4 haloalkylsulfonyl or C2~
C4 alkoxycarbonyl; or (R5)2 when attached to adjacent carbon atoms can be taken together as -
OCF20-, -CF2CF20- or.-OCF2CF20-; and
each R6 is independently H, halogen, CrC4 alkyl, CrC2 alkoxy or C2-C4
15 alkoxycarbonyl, or
each R6 is independently a phenyl or a 5- or 6-membered heteroaromatic ring,
each ring optionally substituted with CrC4 alkyl, C2-C4 alkenyl, C2-C4
alkynyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4
haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, N02, CrC4 alkoxy,
20 C1-C4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, CrG4
alkylsulfonyl, CrC4 alkylarnino, C2-Cg dialkylamino, C3-Cg
cycloalkylamino, C3-C6 (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl,
C2-C6 alkoxycarbonyl, C2-Cg alkylaminocarbonyl, C3-C8
dialkylarninocarbonyl or C3-C6 trialkylsilyl.
25 Preferred C. Compounds of Preferred B wherein
R1 and R2 are both H;
R3 is CrC4 alkyl optionally substituted with halogen, CN, OCH3, S(0)pCH3;
each R4 is independently H, CH3, CF3, OCF3, OCHF2, S(0)pCF3,
S(0)pCHF2, CN or halogen;
30 each R5 is independently CF3, OCF3, OCHF2, S(0)pCF3, S(0)pCHF2,
OCH2CF3, OCF2CHF2, S(0)pCH2CF3 or S(0)pCF2CHF2;
each R6 is independently EL halogen or methyl; or phenyl, pyrazole,
imidazole, triazole, pyridine or pyrimidine, each ring optionally
substituted with Cj-Q alkyl, CrC4 haloalkyl, halogen or CN; and
35 p is 0,1 or 2.
Preferred D. Compounds of Preferred C wherein R3 is i-propyl or f-butyl. Preferred E. Compounds of Formula 1 wherein J is a 5- or 6-membered heteroaromatic rinff ontionallv substituted -with 1 to 4 R7.
WO 01/70671 PCT/US01/09338
Preferred F. Compounds of Preferred E wherein
J is a 5- or 6-membered heteroaromatic ring selected from the group
consisting of J-l, J-2, J-3, J-4 and J-5, each J optionally substituted with 1 to 3 R7
5
Q is 0, S or NR7; and
W, X, Y and Z are independently N or CR7, provided that in J-4 and J-5 at
least one of W, X, Y or Z is N.
Preferred G. Compounds of Preferred E or Preferred F wherein
10 AandBareO;
n is 1 to 2; R1 is H, CrC4 alkyl, CrC4 alkenyl, C2-C4 alkynyl, C2-C6 alkylcarbonyl or
C^-Cg alkoxycarbonyl;
R2 is H, CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C2-C6
15 alkylcarbonyl or C2~C6 alkoxycarbonyl;
R3 is H; or CrC6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or C3-C6 cycloalkyl
each optionally substituted with one or more substituents selected from
the group consisting of halogen, CN, C1-C2 alkoxy, Ci~C2 alkylthio,
C!-C2 alkylsulfinyl and Ci~C2 alkylsulfonyl;
20 one of the R4 groups is attached to the phenyl ring at the 2-position, and said
R4 is CrC4 allcyl, CrC4 haloalkyl, halogen, CN, N02, CrC4 alkoxy,
CrC4 haloalkoxy, C^Q^ alkylthio, CrC4 alkylsulfinyl, Ci~C4
alkylsulfonyl, CrC4 haloalkylthio, CrC4 haloalkylsurfirryl or Ci-Q
haloalkylsulfonyl; and
25 each R7 is independently H, Ci~C4 alkyl, C1 -C4.haloalkyl, halogen, CN, N02,
CrC4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, CrC4 alkylsulfonyl, Ci-C4 haloalkylthio, CrC4 haloalkylsulfiriyl, Cj-Cj haloalkylsulfonyl or C2-C4 alkoxycarbonyl; or a phenyl or a 5- or
WO 01/70671 PCT/US01/09338
6-membered heteroaromatic ring, each ring optionally substituted with
CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, CrC4
haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl,
halogen, CN, N02, CrC4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio,
5 CrC4 alkylsulfinyl, Cj-Q alkylsulfonyl, CrC4 alkylamino, C^-Cg
dialkylamino, C3-C6 cycloalkylamino, C3-C6 (alkyl)cycloa!kylamino,
C2-C4 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6
alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl or C3-C£ trialkylsilyl.
Preferred H. Compounds of Preferred G wherein
10 J is selected from the group consisting of pyridine, pyrirnidine, pyrazole,
imidazole, triazole, thiophene, thiazole and oxazole, furan, isothiazole and isoxazole, each optionally substituted with 1 to 3 R7. Preferred I. Compounds of Preferred H.wherein
J is selected from the group consisting of pyridine, pyrirnidine,. pyrazole,
15 thiophene and thiazole, each optionally substituted with 1 to 3 R7;
R1 and R2 are both H;
R3 is CrC4 alkyl optionally substituted with halogen, CN, OCH3, S(0)pCH3;
each R4 is independently H, CH3, CF3, OCF3, OCHF2, S(0)pCF3,
S(0)pCHF2, CN or halogen;
20- each R7 is independently H, halogen, CH3, CF3, OCHF2, S(0)pCF3,
S(0)pCHF2s OCH2CF3, OCF2CHF2, S(0)pCH2CF3, S(0)pCF2CHF2;
or phenyl, pyrazole, imidazole, triazole, pyridine or pyrirnidine, each
ring optionally substituted with C1-C4 alkyl, Cj-Q haloalkyl, Cj-C4
alkoxy, C^Q^ haloalkoxy, CrC4 alkylthio, C!-C4 alkylsulfinyl, Ci-C4
25 alkylsulfonyl, halogen or CN; and
p is 0,1 or 2. Preferred J. Compounds ofPreferred I wherein J is a pyridine optionally substituted
with 1 to 3 R7.
Preferred K. Compounds ofPreferred J wherein one R7 is a phenyl optionally
30 substituted with C^C^ alkyl, C^C^. haloalkyl, halogen or CN.
Preferred L. Compounds ofPreferred J wherein one R7 is a pyrazole, imidazole,
triazole, pyridine or pyrirnidine, each ring optionally substituted with Ci~C4
alkyl, C^Q haloalkyl, halogen or CN.
Preferred M. Compounds ofPreferred I wherein J is a pyrirnidine optionally substituted
35 withlto3R7.
Preferred N. Compounds of Preferred M wherein one R7 is a phenyl optionally substituted with Cj-Q^ alkyl, Ci-C4 haloalkyl, halogen or CN.
WO 01/70671 PCT/US01/09338
Preferred 0. Compounds of Preferred M wherein one R7 is a p'yrazole, imidazole,
triazole, pyridine or pyrrolidine, each ring optionally substituted with CrC4
alkyl, C1-C4 haloalkyl, halogen or CN.
Preferred P. Compounds of Preferred I wherein J is a pyrazole optionally substituted
5 with 1 to 3 R7.
Preferred Q. Compounds of Preferred P wherein one R7 is a phenyl optionally
substituted with CyC^ alkyl, CrC4 haloalkyl, halogen or CN.
Preferred R Compounds ofPreferredP wherein one R7 is a pyrazole, imidazole,
triazole, pyridine or pyrimidine, each ring optionally substituted with CrC4
10 alkyl, CrC4 haloalkyl, halogen or CN.
Preferred S. Compounds of Preferred R wherein R7 is a pyridine optionally substituted
with Cj-C4 alkyl, CrC4 haloalkyl, halogen or CN.
Most preferred is the"|6mpound of Formula 1 selected from the group consisting of:
3-memyl-iV'-(l-memylethyl)-2-[[4-(trifluoromethyl)benzoyl]amm
15 2-methyl-iV-[2-methyl-6-[[(l -methylethyl)amino]carbonyl]phenyI]-4-
(trifiuoromethyl)benzamide,
2-methyl-iVr-[2-methyl-6-[[(l-methylemyl)ammoJcarbonyI]phenyl]-6-(trifluoromethyl)-3-pyridme(^rboxainide,
l-ethyl-i^P-memyl^-fKl-methylemylJarnmolcarbonyllphenylJ-S-
20 (trifmoromethyl)- lH-pyrazole-5-carboxamide,
l-(2-fluorophenyl)-iV'-[2-methyl-6-[[(l-memylethyl)annno)carbonyl]phenyl]-3-(trifluoromethyl)-liT-pyrazole-5-carboxamide,
l-(3-cmoro-2-pyridmyl)-A^-[2-memyl-6-[[(l-memylemyl)ammo]carbonyl]phen^
(trifluoromethyl)-lF-pyrazole-5-carboxamide,
25 JV"-[2 (trifluoromethyl)-l-H'-pyrazole-5-carboxamide,
i-bromo-l-(2-chlorophenyl)-JV-[2-methyl-6-[[(l-
methyleihyl)arnmo3carbonyl]phenyl3-lif-pyrazole-5-carboxamide,and
3-bromo-iy"-[2-cUoro-6-[[(l-methylemyl)amino]carbonyl]phenyl]-l-(2-
30 cHorophenyI)-l#-pyrazoIe-5-carboxamide.
Preferred compositions are those comprising compounds of formula 1 as preferred in Preferred 1 through 19, and the specifically preferred compounds above.
As noted above, each J is independently a phenyl group or a naphthyl group substituted with 1 to 2 R5 and optionally substituted with 1 to 3 R6; or each J is 35 independently a 5- or 6-membered heteroaroinatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system wherein each ring or ring system is optionally substituted with 1 to 4 R7. The term "optionally substituted" in connection with these J groups refers to groups which are unsubstituted or have at least one non-hydrogen substituent that does not
WO 01/70671 PCT/US01/09338
extinguish the arthropodicidal activity possessed by the unsubstituted analog. Note also that J-l through J-5 above denote 5- or 6-membered heteroaromatic rings. An example of phenyl substituted with 1 to 2 R5 and optionally substituted with 1 to 3 R6 is tiie ring illustrated as J-6 in Exhibit 1, wherein m is an integer from 1 -2 and q is an integer from 1 to 3. Note that 5 at least one R5 must be present in J-6. Although R6 groups are shown in the structure J-6, it is noted that they do not need to be present since they are optional substituents. An example of a naphthyl group substituted with 1 to 2 R5 and optionally substituted with 1 to 3 R6 is J-59 illustrated in Exhibit 1, wherein m is an integer from 1-2 and q is an integer from 1 to 3. Note that at least one R5 must be present in J-59. Although R6 groups are shown in the
10 structure J-59, it is noted that they do not need to be present since they are optional
substituents. Examples of 5- or 6-membered heteroaromatic ring optionally substituted with 1 to 4 R7 include the rings J-7 through J-5 8 illustrated in Exhibit 1 wherein r is an integer from 1 to 4. Note that J-7 through J-26 are examples of J-l, J-27 through J-41 are examples of J-2, J-42 through J-44 are examples of J-3, J-46 through J-53 are examples of J-4 and J-54
15 through J-58 are examples of J-5. The nitrogen atoms that require substitution to fill their valence are substituted with R7. Note that some J groups can only be substituted with less than 4 R7 groups (e.g. J-19, J-20, J-23 through J-26 and J-3 7 through J-40 can only be substituted with one R7). Examples of aromatic 8-, 9- or 10-membered fused heterobicyclic ring systems optionally substituted with 1 to 4 R7 include J-60 through J-90 illustrated in
20 Exhibit 1 wherein r is an integer from 1 to 4. Although R7 groups are shown in the
structures J-7 through J-58 and J-60 through J-90, it is noted that they do not need to be present since they are optional substituents. Note that when R5, R6 and/or R7 are H when attached to an atom, this is the same as if said atom is unsubstituted. Note that when the attachment point between (R5)m, (R6)q or (R7)r and the J group is illustrated as floating,
25 (R5)m, (R6)q or (R7)r can De attached to any available carbon atom of the J group. Note that when the attachment point on the J group is illustrated as floating, the J group can be attached to the remainder of Formula 1 through any available carbon of the J group by replacement of a hydrogen atom.

VWO 01/70671PCIYUS01/09338

As noted above, G is a 5- or 6-membered nonaromatic carbocyclic or heterocyclic ring, optionally including one or two ring members selected from the group consisting of C(=0), SO or S(0)2 and optionally substituted with 1 to 4 substituents selected from the 5 group consisting of C^-Cj alkyl, halogen, CN, N02 and CrC2 alkoxy. The term "optionally substituted" in connection with these G groups refers to groups which are unsubstituted or have at least one non-hydrogen substituent that does not extinguish the arthropodicidal activity possessed by the unsubstituted analog. Note that when the attachment point on the G group is illustrated as floating, the G group can be attached to the remainder of Formula 1 10 through any available carbon of the G group by replacement of a hydrogen atom. The
optional substituents can be attached to any available carbon by replacing a hydrogen atom. Examples of 5- or 6-membered nonaromatic carbocyclic rings as G include the rings illustrated as G-l through G-8 of Exhibit 2, wherein such rings are optionally substituted with 1 to 4 substituents selected from the group consisting of C^-C^ alkyl, halogen, CN, N02 15 and CyC2 alkoxy. Examples of 5- or 6-membered nonaromatic heterocyclic rings as G include the rings illustrated as G-9 through G-48 of Exhibit 2, wherein such rings are optionally substituted with 1 to 4 substituents selected from the group consisting of C^^ alkyl, halogen, CN, N02 and C^-C^ alkoxy. Note that when G comprises a ring selected from G-31 through G-34, G-37 and G-38, Q1 is selected from O, S or N. Note that when G 20 is G-ll, G13, G-14, G16, G-23, G-24, G-30 through G-34, G-37 and G-38 and Q1 isN, the nitrogen atom can complete its valence by substitution with either H or CJ-C2, alkyl.
7

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^ As noted above, each R6 and each R7 can be independently (among others) 5- or 6-
membered heteroaromatic rings or aromatic 8-, 9- or 10-membered fused heterobicyclic ring systems, each ring optionally substituted with one to three substituents independently selected from tbe group consisting of CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 5 cycloalkyl, CrC4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, N02, CrC4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, CrC4 aUkylsulfonyl, Cx-Q alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C3-C6 (allcyl)cycloalkylaniino, C2-C4 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl or C3-Cg trialkylsilyl. Examples of such
10 R6 and R7 groups include the rings or ring systems illustrated as rings J-7 through J-58 and J-60 through J-90 illustrated in Exhibit 1, except that such rings are optionally substituted with 1 to 3 substituents selected from the group consisting of CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, CrC4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, CrC6 halocycloalkyl, halogen, CN, N02, Ci~C4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio,
15 CrC4 alkylsulflnyl, CrC4 alkylsulfonyl, CrC4 alkylamino, Cj-Cg dialkylarnino, C3-C6 cycloalkylamino, C3-C6 (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-Cg alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl or C3-C6 trialkylsilyl rather than (R7)r Note that these substituents can be attached to any available carbon atom of the J group by replacement of a hydrogen atom. Note mat when the
20 attachment point on the J group is illustrated as floating, the J group can be attached to the remainder of Formula 1 through any available carbon of the J group by replacement of a hydrogen atom.
One or more of the following methods and variations as described in Schemes 1-17 can be used to prepare the compounds of Formula 1. The definitions of A, B, J, R1, R2, R3,
25 R4, R5, R6, R7, m and n in the compounds of Formulae 1-34 below are as defined above in the Summary of the Invention. Compounds of Formulae la-c, 2a-b, 4a-g, 5a-b are various subsets of the compounds of Formula 1,2,4 and 5.
Compounds of Formula 1 can be prepared by procedures outlined in Schemes 1-17. A typical procedure is detailed in Scheme 1 and involves coupling of an anthranilic amide of .
30 Formula 2 with an acid chloride of Formula 3 in the presence of an acid scavenger to provide the compound of Formula la. Typical acid scavengers include amine bases such as triethylarnine, diisopropylemylarnine and pyridine; other scavengers include hydroxides such as sodium and potassium hydroxide and carbonates such as sodium carbonate and potassium carbonate. In certain instances it is useful to use polymer-supported acid scavengers such as
35 polymer-bound diisopropylemylarnine and polymer-bound dimethylammopyridine. In a
subsequent step, amides of Formula la can be converted to thioamides of Formula lb using a variety of standard thip transfer reagents including phosphorus.pentasulfide and Lawesson's reagent
WO 01/70671 PCT/US01/09338

An alternate procedure for the preparation of compounds of Formula la involves coupling of an anthranilic amide of Formula 2 with an acid of Formula 4 in the presence of a 5 dehydrating agent such as dicyclohexylcarbodiimide (DCC). Polymer supported reagents are again useful here, such as polymer-bound cyclohexylcarbodiimide. Synthetic procedures of Schemes 1 and 2 are only representative examples of useful methods for the preparation . of Formula 1 compounds as-the synthetic literature is extensive for this type of reaction.
10
One skilled in the art will also realize that acid chlorides of Formula 3 may be prepared from acids of Formula 4 by numerous well-known methods.
Anthranilic amides of Formula 2a are typically available from the corresponding
15 2-Ditrobenzamides of Formula 5 via catalytic hydrogenation of the nitro group. Typical procedures involve reduction with hydrogen in the presence of a metal catalyst such as palladium on carbon or platinum oxide and in hydroxylic solvents such as ethanol and isopropanol. These procedures are well documented in the chemical literature. R1 substituents such as alkyl, substituted alkyl and the like can generally be introduced at this
20 stage through known procedures including either direct alkylation or through the generally preferred method of reductive alkylation of the amine. A commonly employed procedure is to combine the aniline 2a with an aldehyde in the presence of a reducing agent such as sodium cyanoborohydride to produce the Formula 2b compounds where R1 is alkyl, alkenyl, aSk^nyl ox substituted derivatives thereof.
WO 01/70671 PCTYUS01/09338

The intermediate amides of Formula 5a are readily prepared from commercially 5 available 2-nitrobenzoic acids. Typical methods for amide formation can be applied here. These include direct dehydrative coupling of acids of Formula 6 with amines of Formula 7 using for example DCC, and conversion of the acids to an activated form such as the acid chlorides or anhydrides and subsequent coupling with amines to form amides of Formula 5a. We have found ethylchloroformate to be an especially useful reagent for this type of reaction 10 involving activation of the acid. The chemical literature is extensive on this type of reaction. Amides of Formula 5a are readily converted to thioamides of Formula 5b by using commercially available thio transfer reagents such as phosphorus pentasulfide and Lawesson's reagent.
15
Benzoic acids of Formula 4 (J is optionally substituted phenyl) are generally well known in the art as are procedures for their preparation. One particularly useful subset of benzoic acids of this invention are 2-methyl-4-perfluoroalkyl benzoic acids of Formula 4a (R5 equals e.g. CF3, C2F5, C3F7). The synthesis for these compounds is outlined in 20 Schemes 5-9. Benzoic acids of Formula 4a may be prepared from the benzonitriles of Formula 8 by hydrolysis. The conditions used may involve the use of a base such as an alkaline metal hydroxide or alkoxide (e.g. potassium or sodium hydroxide) in a solvent such as water, ethanol or ethylene glycol (e.g. J. Chem. Soc. 1948,1025). Alternatively, the

WO 01/70671 PCT/US01/09338
V.
hydrolysis may be carried out using an acid such, as sulfuric acid or phosphoric acid in a
suitable solvent such as water (e.g. Org. S^mth. 1955, Coll vol. 3, 557). The choice of the
conditions is contingent on the stability of R5 to the reaction conditions and elevated
. temperatures are usually employed to achieve this transformation.

5 Nitriles of Formula 8 may be prepared from anilines of Formula 9 by the classical
sequence involving diazotization and treatment of the intermediate diazonium salt with a copper cyanide salt (e.g. J. Amer. Chem. Soc. 1902,24,1035).
Scheme 6

Anilines of Formula 9 may be prepared from compounds of Formula 10. This 10 transformation may be achieved by a well-known procedure that employs Raney Nickel (Org. Synth. Coll. Vol VI, 581). Alternatively, the same transformation may be effected by the use of a suitable catalyst such as palladium in the presence of hydrogen. The reaction is visually conducted at pressures of 102 to 105 kPa in a suitable organic solvent such as, but not limited to, toluene. Elevated temperatures of 80-110°C are usually required to achieve 15 the transformation. As one skilled in the art will realize, numerous chemical modifications of the thioether moiety are possible, and may be employed when necessary to facilitate this transformation.

WO 01/70671 PCT/US01/09338

Compounds of Formula 10 may be prepared from immosuliuranes of Formula 11. The transformation may be achieved in a protic solvent such as methanol or water, in a non-protic solvent such as dichloromethane or toluene in the presence of a suitable base such as triethylamine (e.g. Org. Synth. Coll. Vol. VI, 581) or sodium methoxide, or in a 5... /combination of a protic solvent, a protic solvent and a base. The temperature at which the reaction is conducted is usually in the range 40-110°C. As one skilled in the art will realize, suitable salts of compounds of Formula 11 such as, but not limited to a hydrochloride, a sulfate or a bisulfate may also be employed, provided that the appropriate amount of base is first used to generate the free base 11. This may be done as a separate step or as an integral 10 part of the step involving the transformation of compounds of Formula 11 to compounds of Formula 10.
Compounds of Formula 11 may be prepared from anilines of Formula 12 by reaction with dimethyl sulfide and a suitable chlorinating agent such as, but not limited to
15 ' iV-cHorosuccinirtude (e.g. Org. Synth. Coll. Vol. VI, 581), chlorine or
iV-chlorobenzotriazole. Alternatively, anilines of Formula 12 may be treated with dimethyl sulfoxide which has been "activated" by treatment with an agent such as acetic anhydride, trifluoroacetic, anhydride, trifluoromethanesulfonic anhydride, cyclohexylcarbodiimide, sulfur trioxide, or phosphorus pentoxide. The reaction is conducted in a.suitable organic
20 solvent such as dichloromethane or dimethyl sulfoxide. The reaction is conducted at a temperature of-70°C to 25°C and is dependent on the solvent and reagent used.

WO 01/70671 PCT/US01/09338

Intermediate anthranilic amides of Formula 2a and 2b may also be prepared from isatoic anhydrides of Formula 13 and 14 (Scheme 10). Typical procedures involve combination of equimolar amounts of the amine 7 with the isatoic anhydride in polar aprotic 5 solvents such as pyridine and dimethylformamide at temperatures ranging from room
temperature to 100° C. R1 substituents such as alkyl and substituted alkyl may be introduced by the base catalyzed alkylation of isatoic anhydride 13 with known alkylating reagents RJ-Lg (wherein Lg is a leaving group such as halogen, alkyl or aryl suphonates or alkyl sulfates) to provide the alkyl substituted intermediates 14. Isatoic anhydrides of Formula 13 10 may be made by methods described in Coppola, Synthesis 505-36 (1980).

An alternate procedure for the preparation of specific compounds of Formula 1 (where A is Q, B is O and RJ is H) involves reaction of an amine 7 with a benzoxaainone of Formula 15. Typical procedures involve combination of the amine with the benzoxazinone 15 in solvents such as tetrahydrofuran or pyridine at temperatures ranging from room
WO 01/70671 PCT/US01/09338
temperature to the reflux temperature of the solvent. Benzoxazinones are well documented in the chemical literature and are available via known methods that involve the coupling of either an anthranilic acid or an isatoic anhydride with an acid chloride. For references to the synthesis and chemistry of Benzoxazinones see Jakobsen et al, Biorgarde and Medicinal 5 Chemistry, 2000, 8, 2095-2103 and references cited within. See also Coppola, J, Heterocyclic Chemistry, 1999,36,563-588.

Heterocyclic acids 4, where J is equal to an optionally substituted heterocycle, can be prepared by procedures outlined in Schemes 12-17. Both general and specific references to
10 a wide variety of heterocyclic acids including thiophenes, furans, pyridines, pyrimidines, triazoles, imidazoles, pyrazoles, thiazoles, oxazoles, isothiazoles, thiadiazoles, oxadiazoles, triazines, pyrazines, pyridazines, and isoxazoles can be found in the following compendia: Rodd's Chemistry of Chemistry of Carbon Compounds, Vol. IVa to IVL, S. Coffey editor, Elsevier Scientific Pubhshing, New York, 1973; Comprehensive Heterocyclic Chemistry,
15 Vol. 1-7, A. R. Katritzky and C. W. Rees editors, Pergamon Press, NewYork, 1984;
Comprehensive Heterocyclic Chemistry II, Vol. 1-9, A. R. Katritzky, C. W. Rees, and E. F. Scriven editors, Pergamon Press, NewYork, 1996; and the series, The Chemistry of Heterocyclic Compounds, E. C. Taylor, editor, Wiley, New York. Particularly useful heterocyclic acids of this invention include pyridine acids, pyrimidine acids and pyrazole
20 acids. Procedures for the synthesis of representative examples of each are detailed in
Schemes 12-17. A variety of heterocyclic acids and general methods for their synthesis may be found in World Patent Application WO 98/57397.
The synthesis of representative pyridine acids (4b) is depicted in Scheme 12. This procedure involves the known synthesis of pyridines from p-ketoesters and 4-
25 aminobutenones (19), Substituent groups R7(a) and R7(b) include e.g. alkyl and haloalkyl.
WO 01/70671 PCT/US01/09338

The synthesis of representative pyrimidine acids (4c) is depicted in Scheme 13. This procedure involves the known synthesis of pyrimidines from vinylidene-p-ketoesters (22) 5 and amidines. Substituent groups R7(a) and R7(b) include e.g. alkyl and haloalkyl.

The synthesis of representative pyrazole acids (4d-4g) is depicted in Schemes 14-17. Pyrazoles 4d are described in Scheme 14. The synthesis of Scheme 14 involves as the keyWO 01/70671 PCT7US01/09338
step introduction of the R7(b) substituent via alkylation of the pyrazole. The alkylating agent R7(b)-Lg (wherein Lg is a leaving group such as CI, Br, I, sulfonates such as p-toluenesulfonate or methanesulfonate or sulfates such as -S02OR7(b)) includes R7(b) groups such as CrC6 alkyl, C2-C6 alkenyl, CyCs alkynyl, C3-C6 cycloalkyl, CrC6 haloalkyl, C2-5 C6 haloalkenyl, C2-C6 haloalkynyl, C3-Cg halocycloalkyl, C2-C6 alkylcarbonyl, C2-C6 alkoxycarbonyl, C3-Cg dialkylaminocarbonyl, C3-C6 trialkylsilyl; or phenyl, beazyl, benzoyl, 5- or 6-membered heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system, each ring or ring system optionally substituted. Oxidation of the methyl group affords the pyrazole carboxylic acid. Some of the more preferred R7(a) groups 10 include haloalkyl.

Pyrazoles 4e are described in Scheme 15. These pyrazole acids may be prepared via metallation and carboxylation of pyrazoles of formula 28 as the key step. The R7(b) group is introduced in a manner similar to that of Scheme 14, i.e. via alkylation with a R7(b) 15 alkylating agent. Representative R7(a) groups include e.g. cyano, and haloalkyl.

WO 01/70671 PCTVTJS01/09338

Pyrazoles 4f are described in Scheme 16. These can be prepared via reaction of an optionally substituted phenyl hydrazine 29 with a pyruvate 3 0 to yield pyrazole esters 31. Hydrolysis of the ester affords the pyrazole acids 4f. This procedure is particularly useful 5 for the preparation of compounds where R (b) is optionally substituted phenyl and R (a) is haloalkyl.

WO 01/70671 PCT/US01/09338

Pyrazoles acids of Formula 4g are described in Scheme 17. These can be prepared via 3+2 cycloaddition of an appropriately substituted nitrilimine with either substituted propiolates (33) or acrylates (36). Cycloaddition with acrylates requires additional oxidation 5 of the intermediate pyrazoline to the pyrazole. Hydrolysis of the ester affords the pyrazole acids 4g. Preferred irninohalides for this reaction include the trifiuorornethyl irninochloride (38) and the irninodibromide (39). Compounds such as 38 are known (J. Heterocycl Chem. 1985,22(2), 565-8). Compounds such as 39 are available by known methods (Tetrahedron Letters 1999, 40,2605). These procedures are particularly useful for the preparation of 10 compounds where R7(b) is optionally substituted phenyl and R7(a) is haloalkyl or bromo.

WO 01/70671 PCT/US01/09338

It is recognized that some reagents and reaction conditions described above for preparing compounds of Formula 1 may not be compatible with certain functionalities present in the intermediates. In these instances, the incorporation of protection/deprotection 5 sequences or functional group interconversions into the synthesis will aid in obtaining the desired products. The use and choice of the protecting groups will be apparent to one skilled in chemical synthesis (see, for example, Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991). One skilled in the art will recognize that, in some cases, after the introduction of a given reagent as it is depicted in any 10 individual scheme, it may be necessary to perform additional routine synthetic steps not
described in detail to complete the synthesis of compounds of Formula 1. One skilled in the art will also recognize that it may be necessary to perform a combination of the steps illustrated in the above schemes in an order other than that implied by the particular sequence presented to prepare the compounds of Formula 1.
WO 01/70671 PCT/US01/09338
One skilled in the art will also recognize that compounds of Formula 1 and the
intermediates described herein can be subjected to various electrophilic, nucleophilic,
radical, organometallic, oxidation, and reduction reactions to add substituents or modify
existing substituents.
5 Without further elaboration, it is believed that one skilled in the art using the
preceding description can utilize the present invention to its fullest extent. The following Examples are, therefore, to be construed as merely illustrative, and not limiting of the disclosure in any way whatsoever. Percentages are by weight except for chromatographic solvent mixtures or where otherwise indicated. Parts and percentages for chromatographic 10 solvent mixtures are by volume unless otherwise indicated. *H NMR. spectra are reported in ppm downfield from tetramethylsilane; s is singlet, d is doublet, t is triplet, q is quartet, m is multiplet, dd is doublet of doublets^dt is doublet of triplets, br s is broad singlet.
EXAMPLE 1
Step A: Preparation of 3-memyl-A^O-memvlethvB-2-nitrobenzarnide
15 .A solution of 3-methyl-2-nitrobenzoic acid (2.00 g, 11.0 mmol) and triethylamine
. (1.22 g, 12.1 mmol) in 25 mL of methylene chloride was cooled to 10°C. Ethyl chloroformate was carefully added and a solid precipitate formed. After stirring for 30 minutes isopropylarnine (0.94 g, 16.0 mmol) was added and a homogeneous solution resulted. The reaction was stirred for an additional hour, poured into water and extracted 20 with ethyl acetate. The organic extracts were washed with water, dried over magnesium
sulfate and evaporated under reduced pressure to afford 1.96 g of the desired intermediate as a white solid melting at 126-128 °C.
iHNMR (CDC13) 8 1.24 (d\6H), 2.38 (s,3H), 4.22 (m,lH), 5.80 (br s,lH), 7.4 (m,3H).
StepB: Preparation of 2-amino-3 -methvl-JV-f 1 -methvletfayDbenzamide
25 The 2^nitrobenzamide of Step A (1.70 g, 7.6 mmol) was hydrogenated over 5% Pd/C
in 40 mL of ethanol at 50 psi. When the uptake of hydrogen ceased the reaction was filtered through celite and the celite was washed with ether. The filtrate was evaporated under reduced pressure to afford 1.41 g of the title compound as a solid melting at 149-151 °C.
!HNMR (CDCI3) 5 1.24 (dd,6H), 2.16 (s,3H), 4.25 (m,lH), 5.54 (br s72B), 5.85 (br 30 s,lH), 6.59 (UH), 7.13 (d,lH), 7.17 (d,lH).
Step C: Preparation of 3-methvl-iV- rtrifluoromemoxv)berizovllarnmoTberizamide 4-(trifluoromethoxy)benzoyl chloride (0.29 g, 1.3 mmol) was added dropwise to a mixture of the aniline from Step B (0.25 g, 1.3 mmol) and triemylamine (0.13 g, 1.3 mmol) 35, in 5 mL of methylene chloride at room temperature. After stirring for one hour the reaction was poured into water and extracted with ethyl acetate. The combined extracts were dried over magnesium sulfate and evaporated under reduced pressure. The resulting solids were
WO 01/70671 PCT/US01/09338
washed with hexane/ether and filtered to afford 0.41 g of the title compound, a compound of the present invention, as a solid melting at 207-209°C.
1HNMR (CDCI3) 6 1.19 (d, 6H), 2.33 (s, 3H), 4.15 (m, 1H), 5.97 (br d, 1H), 7.2-7.4 (m, 6H), 8.04 (d, 1H), 10.11 (br s51H).
5 EXAMPLE 2
Step A: Preparation of l-Ethvl-34rifluoromethylpyrazol-5-yl Carboxylic acid
To a mixture of 3-trifiuoromethylpyrazole (5 g, 37 mmol) and powdered potassium carbonate (10 g, 72 mmol) stirring in 30 mL of i^iV-dimethylformamide, iodoethane (8 g, 51 mmol) was added dropwise. After a mild exotherm, the reaction was stirred overnight at
10 room temperature. The reaction mixture was partitioned between 100 mL of diethyl ether and 100 mL of water. The ether layer was separated, washed with water (3X) and brine, and dried over magnesium sulfate. Evaporation of solvent in vacuo gave 4 g of oil.
To 3.8 g of this oil stirring in 40 mL of tetrahydrofuran under nitrogen in a dry ice/acetone bath, 17 mL of a 2.5 M solution of w-butyl lithium in tetrahydrofuran (43 mmol)
15 was added dropwise and the solution stirred for 20 minutes at -78°C. An excess of gaseous carbon dioxide was bubbled into the stirred solution at a moderate rate for 10 minutes. After addition of carbon dioxide, the reaction was allowed to slowly reach room temperature and stirred overnight. The reaction mixture was partitioned between diethyl ether (100 mL) and 0.5 N aqueous sodium hydroxide (100 mL). The basic layer was separated and acidified
20 with concentrated hydrochloric acid to a pH of 2-3. The aqueous mixture was extracted with ethyl acetate (100 mL) and. the organic extract washed with water and brine and dried over magnesium sulfate. The oily residue, which remained after evaporating the solvent in vacuo, was triturated to a solid from a small amount of H-butyl chloride. After filtering and drying, a slightly impure, sample of l-emyl-3-trifluoromethyl-pyrazol-5-yl carboxylic acid (1.4 g)
25 was obtained as a broad-melting solid.
JH NMR (CDCI3): 9.85 (br s,lH), 7.23 (s,lH), 4.68 (q,2H), 1.51 (t,3H) ppm.
Step B: Preparation of 2-[l-Ethvl-3-trifluoromethylpvrazol-5-vl carbamovl"l-3-
methvl-iV-d -methvlethvDbenzamide To a solution of l-ethyl-3-trifluoromethyl-pyrazol-5-yl carboxylic acid (0.5 g,
30 2.4 mmol) stirring in 20 mL of methylene chloride, oxalyl chloride (1.2 mL, 14 mmol) was added. Upon addition of 2 drops of JV.iV'-dimethylfonnamide, foaming and bubbling occurred. The reaction mixture was heated at reflux for 1 hr as a yellow solution. After cooling, the solvent was removed in vacuo and the resulting residue dissolved in 20 mL of tetrahydrofuran. To the stirred solution, 2-amino-3-methyl-A^-(l-memylethyl)benzamide
35 (0.7 g, 3.6 mmol) was added followed by the dropwise addition of N,N-
diisopropylemylarnine (3 mL, 17 mmol). After stirring at room temperature overnight, the reaction mixture was partitioned between ethyl acetate (100 mL) and IN aqueous
WO 01/70671 PCT/US01/09338
hydrochloric acid (75 mL). The separated organic layer was washed with water and brine and dried over magnesium sulfate. Evaporating in vacuo gave a white solid residue, which on purification by flash column chromatography on silica gel (2:1 hexanes/ethyl acetate) afforded 0.5 g of the title compound, a compound of the present invention, melting at 5 223-226°C.
^NMRCDMSO-De): 10.15 (s,lH), 8.05 (d,lH), 7.45 (s,lH), 7.43-7.25 (m,3H), 4.58 (q,2H), 3.97 (m,lH), 2.45 (ss3H), 1.36 (t,3H), 1.06 (d,6H) ppm.
EXAMPLE 3
Step A: Preparation of S.S-dimemvl-i\T-[4-rtrifluoromemvDphenvl]sulfilimine
10 A solution of N-cMorosucciinmide (12-43 g, 93.1 mmol) in ~170 mL of
dichloromethane was added to a mixture of 4-(trifluoromethyl) aniline (15 g, 93.1 mmol) and dimethyl sulfide (6.35 g, 102 mmol) in 230 mL of dichloromethane at-5-0°C. After the addition was complete, the mixture was stirred at 0-5°C for lh, and iV-chlorosuccinrmide (0.02 g, 4.64 mmol) was added. After a further 30 minutes, the mixture was washed with
15 500 mL of IN sodium hydroxide.
The organic phase was dried and evaporated to give the product as a solid 19-72 g melting at 101-103 °C (after crystallization from ethyl acetate/hexanes).
rR(Nujol) 1603,1562,1532,1502,1428,1402,1335,130Q, 1270,1185, 1150,1103, 1067,1000, 972, 940, 906, 837, 817 cm"1.
20 lB NMR"(CDC13) 5 7.35 (d, J=8.8 Hz, 2 H), 6.84 (d, J=8.8 Hz, 2 H), 2.67 (5,3 H).
Step B: 2-[rmethylthio^methvl1-4-(rtrffluoromethvl)benzenamine
. Sodium methoxide in methanol (1.95 g, 9.02 mmol, 25%) was added to S,S-dimemyl-A^-[4-(trifluoromemyl)phenyl]sulfm^nine from Step A (2 g, 9.04 mmol) in 15 mL of toluene. The mixture was warmed to ~80°C for -1 h. The mixture was allowed to cool to
25 25°C and was poured into 100 mL of water. The mixture was extracted with 2x100 mL of ethyl acetate and the combined extracts were dried and evaporated to give 1.8 g of the product as a solid melting at 65.5-67.5°C (after crystallization from hexanes).
IR(nujol) 3419, 3333,1629,1584,1512,1440,1334,1302,1235,1193,1139,1098, 1078, 979, 904, 832 cm"1.
30 !HNMR (CDC13) 5 7.35 (dd, J=1.5 Hzx 8.2 Hz, 1H) 6.72 (d, J=8.4 Hz) 4.39 (br.5,
2 H, 3.69 (5,2 H), 1.99 (5,3 H).
Step C: Preparation of 2-methvl-4-rtrifluoromethvl)benzenamine
Activated Raney nickel (500 g wet paste, ~50u) was added portionwise to a solution of 2-[(memyltMo)memyl]-4-(1rifluoromemyi)benzenamme (55.3 g, 0.25 mole) in 1 L of
35 ethanol over 30 minutes at 25-30° C. The heterogeneous mixture was stirred vigorously for 30 minutes after the addition. The stirring was stopped, and the solids were allowed to settle over one hour. The liquid was decanted from the solids and poured through filter paper.
WO 01/70671 PCT/US01/09338
The filtrate was evaporated under reduced pressure, and the residue was taken up in
dichloromethane. The organic phase was separated from a small volume of water, dried over
magnesium sulfate and evaporated under reduced pressure to afford 37.6g of the title
compound as amber oil.
5 !HNMR (CDGI3) 5 7.28 (m,2H), 6.68 (d,lH), 3.87 (br s,2H), 2.19 (s,3H).
Step D: Preparation of 2-me1hvl-44trifluoromethvl>)benzonitrile
Concentrated hydrochloric acid (16 mL) was added dropwise at a moderate rate to a heterogeneous mixture of 2-methyl^(triiluoromemyl)benzenamine (14 g, 80 mmol) and 120 mL of water while stirring vigorously. A thick suspension resulted which was stirred for
10 20 minutes, diluted with 280 mL of water and cooled to 5° C. A solution of sodium nitrite (5.5 g, 80 mmol) and 25 mL of water was added slowly to the reaction suspension. After stirring for 30 minutes at 5° C a solution resulted which was stirred cold for 30 more minutes and then neutralized with potassium carbonate. This diazonium salt solution was then added portionwise via cannula to a stirred, 95 ° C mixture of potassium cyanide (22 g, 0.34 mole),
15 copper sulfate pentahydrate (20 g, 80 mmol) and 140 mL of water. After the addition the mixture was stirred for 30 minutes at 95° C and then allowed to cool to room temperature. Ether was added and the heterogeneous mixture was filtered through celite. The solids were washed with ether, and the filtrate was partitioned. The aqueous phase was extracted with ether, and the combined organic extracts were dried over magnesium sulfate and
20 concentrated under reduced pressure to afford 13.1 g of the title compound as brown oil.
]H NMR (CDCI3) 8 7.74 (d,lH), 7.60 (s,lH), 7.55 (d,lH), 2.64 (s,3H).
Step E: Preparation of 2-methvl-4-trifluoromethyl benzoic acid
Potassium hydroxide (15.7 g, 0.28 mole) and 15 mL of water were added as a solution to a stirred, heterogeneous mixture of 2-memyl^(trifluoromemyl)benzordtrile (13
25 g, 70 mmol) and 135 mL of ethylene glycol. The reaction mixture was heated at 120-130° C for 20 hours and allowed to cool to room temperature. The dark solution was poured into 800 mL of water and filtered through celite. The filtrate was washed with ether and then the aqueous was acidified with concentrated hydrochloric acid. This aqueous phase was extracted three times with ethyl acetate, the organic extracts were combined, dried over
3 0 magnesium sulfate and evaporated under reduced pressure to afford the title compound as a tan solid.
*H NMR (CDCI3) 5 7.98 (d,lH), 7.70 (s,lH), 7.65 (d,lH), 2.60 (s,3H).
Step F: Preparation of 2-methvl-4-rtrifluoromethoxv')benzovl chloride
Thionyl chloride (0.42 g, 3.5 mmol) was added to a solution of the benzoic acid from
35 Step E (0.50 g, 2.4 mmol) in 10 mL of toluene at room temperature. The reaction was
refiuxed for three hours then cooled to room temperature. The solvent was evaporated under reduced pressure and excess thionyl chloride was removed by azeotroping with toluene. The benzoyl chloride obtained was used directly in Step G.

WO 01/70671 PCT/US01/09338
Step G: Preparation of 2-methvl-JV-r2-metfavl-6-rrn -me&vlethvDaminol--
carbonvl]phenvl1-44trifluorometfavl'>beDzamide The benzoyl chloride of Step F (0.29 g, 1.3 mmol) was added to a mixture of the aniline from Example 1, Step B (0.36 g, 1.9 mmol) and diisopropylethylamine (0.26 g, 5 2.0 mmol) in 10 mL of chloroform at room temperature. The reaction was allowed to stir ovemight The solid precipitate was filtered and dried to afford 0.38 g of the title compound, a compound of the present invention, as a solid melting at 247-248 °C.
lH NMR (CDC13) a 1.24 (d,6H), 2.41 (s,3H), 2.58 (s,3H), 4.20 (m,lH), 5.94 (br d,lH), 7.2-7.3 (m,2H), 7.40 (d,lH), 7.52 (s,lH), 7.53 (d,lH), 7.70 (d,lH), 9.36 (br s,lH).
10 EXAMPLE 4
Step A: Preparation of 2-Methvl-6-ftrifluoromethvlV3-rjvridinecarbonyl chloride
Thionyl chloride (4.35 g, 36.5 mmol) was added to a mixture of 2-methyl-6-
trifluoromethyl nicotinic acid (5.00 g, 24.4 mmol) in 75 mLof toluene and the mixture was
heated at reflux for 3 hours. The reaction was cooled to room temperature and the solvent
15 was removed under reduced pressure. Excess thionyl chloride was removed by azeotrope
with toluene. The resultant acid chloride was used as is in Example 4, Step B.
Step B: Preparation of 8-Memvl-2-r2-memvl-6-fMfluoromethvlV3-Pvridinvl")-4^-
3,1-benzoxazine A mixture of the 6-methyl isatoic anhydride (3.92 g, 22.1 mmol) and the acid 20 cMoride from Step A (5.45 g, 24.3 mmol) was heated at reflux in pyridine for 16 hours. The dark brown solution was cooled to room temperature and the solvent was removed under reduced pressure. Excess pyridine was removed by azeotrope with toluene. Ether was added and the resulting brown solid was removed by filtration. The solid was taken up in a mixture of aqueous sodium bicarbonate and chloroform, the chloroform extracts were dried 25 over magnesium sulfate and evaporated. Excess pyridine was again removed by azeotrope with toluene to afford 5.1 g of the title compound as a brown solid.
]H NMR (CDCI3) d 2.65 (s,3H), 3.11 (s,3H), 7.49 (t,lH) 7.40 (m,lH), 7.68-7.73 (m,2H), 1.11 (d,lH), 8.58 (d,lH).
Step C: Preparation of 2-Methvl-JV-r2-methvl-6-rr(l-
30 methvlemvl)ammo]carbonvl1phenvll-6-(trifluoromethvlV3-pyridine
Isopropylarnine (7.37 g, 0.125 mmol) was added to a mixture of the benzoxadnone of Step B (4.00 g, 12.5 mmol) in 30 mL of tetrahydrofuran. A homogeneous solution formed. The mixture was heated briefly after which a thick white precipitate formed. The solvent was removed under reduced pressure and the resultant solid was washed with ether 35 and filtered to afford 4.48 g of the title compound as a solid melting at 247-248 C.
!H NMR (CDCI3) d 1.24 (d,6H), 2.41 (s,3H), 2.77 (s,3H), 4.17 (m,lH), 5.96 (bd,lH), 7.21 (m,2H) 7.40 (m,lH), 7.53 (d,lH), 7.97 (d,lH), 9.80 (bs,lH).

WO 01/70671 PCT/US01/09338
EXAMPLES
Step A: Preparation of 4-Methvl-JV-r2-methvl-6-rra-
methvletavnaminolcaTbonvllphenvIj^-faifluoroniethylVS-
pyrimidinecarboxamide
5 To a solution 0.8 g (4 mmol) of 4-methyl-2-trifluoromethylpyrimidine-5-carboxylic
acid [made by the method of Palanki et als J.Med. Chem. 2000,43, 3995] stirring in 15 mL of methylene chloride, oxalyl chloride (2 mL, 23 mmol) was added. Upon addition of 2 drops of iV^iV'-dimethylformamide, foaming and bubbling occurred. The reaction mixture was heated at reflux for 1 hr as a yellow solution. After cooling, the solvent was removed in 10 vacuo and the resulting residue dissolved in 20 mL of tetrahydrofuran. To the stirred
solution, 2-amino-3-memyl-iV-(l-memylethyl)benzamide (1 g, 5 mmol) was added followed by the drop wise addition of N.N-du^opropylemylarnine (3 ml, 17 mmol). After stirring at room temperature overnight, the reaction mixture was partitioned between ethyl acetate (200 mL) and IN aqueous hydrochloric acid (75 mL). The separated organic layer was 15 washed with water and brine and dried over magnesium sulfate. Evaporating in vacuo gave a white solid, which was suspended in a small amount of ethyl acetate and filtered to afford (after drying) 650 mg of the title compound, a compound of the present invention, melting at 248-251°C.
'HNMR (DMSO-D6): 10.3 (s,NH), 9.07 (s,lH), 8.25 (d,NH), 7.43-7.25 (m,3H), 4.03 20 (m,lH);2.73 (s,3H), 2.32 (s,3H), 1.12 (d,6H) ppm.
EXAMPLE 6 .
Step A: Preparation of 2-Memyl-l-phenvl-4-('trifluoromethvlVlff-pvrazole
A solution of l,l,l-trifl.uoropentane-2,4-dione (20.0 g, 0.130 mole) in glacial acetic acid (60 mL) was cooled to 7°C using an ice/water bath. Phenylhydrazine (14.1 g, 0.130 25 mole) was added dropwise over a period of 60 minutes. The reaction mass temperature
increased to 15°C during the addition. The resulting orange solution was held under ambient conditions for 60 minutes. The bulk of the acetic acid was removed by stripping on a rotary evaporator at a bath temperature of 65°C. The residue was dissolved in methylene chloride (150 mL). The solution was washed with aqueous sodium bicarbonate (3 g in 50 mL water). 30 The purple-red organic layer was separated, treated with activated charcoal (2 g) and
MgS04, then filtered. Volatiles were removed on a rotary evaporator. The crude product consisted of 28.0 g of a rose-colored oil, which contained ~89% the desired product and 11 % 1 -phenyl-5-(trifluoromethyl)-3-methylpyrazoIe.
^NMR (DMSO-De) 5 2.35 (s,3H), 6.76 (s,lH), 7.6-7.5 (m,5H).

WO 01/70671 PCT/US01/09338
StepB: Preparation of l-Phenvl-3-(trifluoromethyD-lij'-pvrazole-5-carboxvlic ar.id
A sample of crude l-phenyl-3-(trifJuoromethyl)-5-methylpyrazole (~89%, 50.0 g, 0.221 mole) was mixed with water (400 mL) and cetyltrimemylammonium chloride (4.00 g, 0.011 mole). The mixture was heated to 95°C. Potassium permanganate was added in 10 5 equal portions, spaced at -8 minute intervals. The reaction mass was maintained at
95-100°C during this period. After the last portion was added, the mixture was held for ~15 minutes at 95-100°C, whereupon the purple, permanganate color had been discharged. The reaction mass was filtered while hot (~75°C) through a 1 cm thick bed of Celite® on a 150 ml, coarse, glass frit. The filter cake was washed with warm (~50°C) water (3xlO0mL).
10 The combined filtrate and washings were extracted with ether (2x100 mL) to remove a small amount of yellow, water-insoluble material. The aqueous layer was purged with nitrogen to remove residual ether. The clear, colorless alkaline solution was acidified by adding concentrated hydrochloric acid dropwise until the pH reached ~1.3 (28 g, 0.28 mole). Gas evolution was vigorous during the first two-thirds of the addition. The product was collected
15 via filtration, washed with water (3x40 mL), then dried overnight at 55°C in vacuo. The product consisted of 11.7 g of a white, crystalline powder, which was essentially pure based upon *£[ NMR.
]H NMR (CDC13) 8 7.33 (s,lH), 7.4-7.5 (m,5H).
Step C: Preparation of l-Phenvl-S-rtrifluoromethvlVlff-pvrazole-S-carbonyl chloride
20 A sample of crude l-phenyl-3-(trifluoromethyl)pyrazole-5-carboxyhc acid (4.13 g,
16.1 mmol) was dissolved in methylene chloride (45 mL). The solution was treated with oxalyl chloride (1.80 mL, 20.6 mmol), followed by A^A^dimethylformamide (0.010 mL, 0.13 mmol). Off-gassing began shortly after adding the i^AT-dimethylformamide catalyst. The reaction mixture was stirred for ~20 minutes under ambient conditions, then was heated to
25 reflux for a period of 35 minutes. Volatiles were removed by stripping the reaction mixture on a rotary evaporator at a bath temperature of 55°C. The product consisted of 4.43 g of a light-yellow oil. The only impurity observed by *H NMR was i^iV"-dmethylformamide.
lHNMR (CDCI3) 8 7.40 (m,lH), 7.42 (s,lH), 7.50-7.53 (m,4H).
Step D: Preparation of JV'-r2-Memvl-6-[fri-methvlemvnarnmo'|carbonyllphenyl]-l-
30 phenyl-3-(trifluoromemvlVlH-pvrazole-5-carboxamide
A sample of 3-methylisatoic anhydride (0.30 g, 1.7 mmol) partially dissolved in pyridine (4.0 mL) was treated with l-phenyl-3-(trifluoromethylpyrazole)-5-carboxyl chloride (0.55 g, 1.9 mmol). The mixture was heated to ~95°C for a period of 2 hours. The resulting orange solution was cooled to 29°C, then was treated with isopropylarnine (1.00 g, 16,9
35 mmol). The reaction mass self-heated to 39°C. It was further heated to 55°C for a period of 30 minutes, whereupon much precipitate formed. The reaction mass was dissolved in • methylene chloride (150 mL). The solution was washed with aqueous acid (5 mL cone. HC1 in 45 mL water), then with aqueous base (2 g sodium carbonate in 50 mL water). The
WO 01/70671 PCT/US01/09338
organic layer was dried over MgS04, filtered, then concentrated on a rotary evaporator. Upon reduction to ~4 mL, product crystals had formed. The slurry was diluted with -10 mL of ether, whereupon more product precipitated. The product was isolated by filtration, washed with ether (2x10 mL), then washed with water (2x50 mL). The wet cake was dried 5 for 3 0. minutes at 70°C in vacuo. The product consisted of 0.52 g of an off-white powder melting at 260-262°C.
2H NMR (DMSO-D6) 5 1.07 (d,6H), 2.21 (s,3H), 4.02 (octet,lH), 7.2-7.4 (m,3H), 7.45-7.6 (m,6H), 8.10 (d,lH), 10.31 (s,lH).
EXAMPLE 1'
10 Step A: Preparation of 3-Trifluorome&vl-2-r3-(triiluoromethvlVlff-nvrazol-l"
yllpyridine
A mixture of 2-chloro-3-trifluoromethylpyridine (3.62 g., 21 mmol), 3-
trifluoromethylpyrazole (2.7 g., 20 mmol), and potassium carbonate (6.0 g., 43 mmol) were
heated at 100 ° C for 18 h. The cooled reaction mixture was added to ice/water (100 mL).
15 The mixture was extracted twice with ether (100 mL) and the combined ether extracts were
washed twice with water (100 mL). The organic layer was dried with magnesium sulfate
and concentrated to an oil. Chromatography on silica gel with hexanes:ethyl acetate 8:1 to
4:1 as eluent gave the title compound (3.5 g) as an oil. XHNMR (CDC13) 5 6.75 (m,lH), 7.5
(m,lH), 8.2 (m,2H), 8.7 (m,lH).
20 Step B: Preparation of 3-(Trifluoromethyl)-l-[3-(trifluoromethvlV2-pyriduivll-lH-
pyrazole-5-carboxylic acid A mixture of the title compound of Example 5, Step A (3.4 g, 13 mmol) was dissolved in tetrahydrofuran (30 mL) and cooled to - 70 °C. Lithium diisopropylamide ( 2N in heptane/tetrahydrofuran, (Aldrich) 9.5 mL, 19 mmol) was added and the resulting dark 25 mixture was stirred for 10 minutes. Dry carbon dioxide was bubbled through the mixture for 15 minutes. The mixture was allowed to warm to 23 °C and treated with water (50 mL) and 1 N sodium hydroxide (10 mL). The aqueous mixture was extracted with ether (100 mL) and then ethyl acetate (100 mL). The aqueous layer was acidified with 6JVhydrochloric acid to pH 1-2 and extracted twice with dichloromethane. The organic layer was dried with 30 magnesium sulfate and concentrated to give the title compound (1.5 g). !H NMR (CDC13) 5 7.6 (m,lH), 7.95 (m,lH), 8.56 (m,lH), 8.9 (m,lH), 14.2 (br,lH)
Step C: Preparation of Ar-r2-Methvl-6-["[ri -methyiemyl)amino1carbonvllphenyll-3-
ffrifluoromemvl)-l-[3-ftrifluorome^
carboxamide
35 A mixture of the title compound of Example 5, Step B (0.54 g, 1.1 mmol), the title
compound from Example 1, Step B (0.44 g, 2.4 mmol) and bop chloride (bis(2-oxo-oxazoHd^yl)phosphinyl chloride, 0.54 g, 2.1 mmol) in acetonitrile (13 mL) was treated with

WO 01/70671 PCT/US01/09338
triethylamine (0.9 mL). The mixture was shaken in a closed scintillation vial for 18 h. The reaction was partitioned between ethyl acetate (100 mL) and lJVhydrochloric acid. The ethyl acetate layer was washed successively with IN hydrochloric acid (50 mL), IN sodium hydroxide (50 mL) and saturated sodium chloride solution (50 mL). The organic layer was 5 dried over magnesium sulfate and concentrated. The residue was subjected to column chromatography on silica gel with hexanes/ethyl acetate (5:1 to 3:1) as eluent. The title compound (0.43 g) was isolated as a white solid. in.p. 227 -230 °C. 2HNMR (CDC13) 5 1.2 (m, 6H), 4.15 (m, 1H), 5.9 (br d,lH), 7.1 (m,lH), 7.2 (m,2H), 7.4 (s,lH), 7.6 (m,lH), 8.15 (m,lH), 8.74 (m,lH), 10.4 (br,lH).
10 By the procedures described herein together with methods known in the art, the
following compounds of Tables 1 to 17 can be prepared. The following abbreviations are used in the Tables: t is tertiary, s is secondary, n is normal, / is iso, c is cyclo, Me is methyl, Et is ethyl, Pr is propyl, /-Pr is isopropyl, M3u is tert butyl, Ph is phenyl, OMe is methoxy, OEt is ethoxy, SMe is methylthio, SEt is ethylthio, CN is cyano, N02 is nitro,
15 TMS is trimethylsilyl, S(0)Me is methylsulfuryl, and S(0)2Me is methylsulfonyl.

52

WO 01/70671 PCT/US01/09338

Formulation/Utility
Compounds of this invention will generally be used as a formulation or composition with an agriculturally suitable carrier comprising at least one of a liquid diluent, a solid diluent or a surfactant. The formulation or composition ingredients are selected to be , • 5 consistent with the physical properties of the active ingredient, mode of application and environmental factors such, as soil type, moisture and temperature. Useful formulations include liquids such as solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions and/or suspoemulsions) and the like which optionally can be thickened into gels. Useful formulations further include solids such as dusts, 10 powders, granules, pellets, tablets, films, and the like which can be water-dispersible
("wettable") or water-soluble. Active ingredient can be (micro)encapsulated and further formed into a suspension or solid formulation; alternatively the entire formulation of active ingredient can be encapsulated (or "overcoated"). Encapsulation can control or delay release of the active ingredient. Sprayable formulations can be extended in suitable media and used 15 at spray volumes from about one to several hundred liters per hectare. High-strength compositions are primarily used as intermediates for further formulation.
The formulations will typically-contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges that add up to 100 percent by weight.
Weight Percent
Active
Ingredient Diluent Surfactant
Water-Dispersible and Water- 5-90 0-94 1-15
soluble Granules, Tablets and
Powders.
Suspensions, Emulsions, 5-50 40-95 0-15
Solutions (including Emulsifiable Concentrates)
Dusts 1-25 70-99 0-5
Granules and Pellets 0.01-99 5-99.99 0-15
High Strength Compositions 90-99 0-10 0-2
Typical solid diluents are described in Watkins, et al., Handbook of Insecticide Dust 20 Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey. Typical liquid
diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950. McCutcheon 's Detergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, New Jersey, as well as Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ.
WO 01/70671 PCT/US01/09338
Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth and the like, or thickeners to increase viscosity.
Surfactants include, for example, polyethoxylated alcohols, polyethoxylated 5 alkylphenols, polyethoxylated sorbitan fatty acid esters, dialkyl sulfosuccinates, alkyl sulfates, alkylbenzene sulfonates, organosilicones, A^-dialkyltaurates, lignin sulfonates, naphthalene sulfonate formaldehyde condensates, polycarboxylates, and. polyoxyethylene/polyoxypropylene block copolymers. Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, starch, sugar, silica, talc,
10 diatomaceous earth, urea, calcium carbonate,.sodium carbonate and bicarbonate, and sodium sulfate. Liquid diluents include, for example, water, iV^-dimqthylformarnide, dimethyl sulfoxide, iV-alkylpyrrolidone, ethylene glycol, polypropylene glycol, paraffins, alkylbenzenes, alkylnaphthalenes, oils of olive, castor, linseed, rung, sesame, corn, peanut, cotton-seed, soybean, rape-seed and coconut, fatty acid esters, ketones such as
15 cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, and alcohols such as methanol, cyclohexanol, decanol and tetrahydrofurfuryl alcohol.
Solutions, including emulsifiable concentrates, can be prepared by simply mixing the ingredients. Dusts and powders can be prepared by blending and, usually, grinding as in a hammer mill or fluid-energy mill. Suspensions are usually prepared by wet-milling; see, for
20 example, U.S. 3,060,084. Granules and pellets can be prepared by spraying the active
material upon preformed granular carriers or by agglomeration techniques. See Browning, "Agglomeration", Chemical Engineering, December 4,1967, pp 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and following, and WO 91/13546. Pellets can be prepared as described in U.S. 4,172,714.
25 Water-dispersible and water-soluble granules can be prepared as taught in U.S. 4,144,050, U.S. 3,920,442 and DE 3,246,493. Tablets can be prepared as taught in U.S. 5,180,587, U.S. 5,232,701 and U.S. 5,208,030. Films can be prepared as taught in GB 2,095,558 and U.S. 3,299,566.
For further information regarding the art of formulation, see U.S. 3,235,361, Col. 6,
30 line 16 through Col. 7, line 19 and Examples 10-41; U.S. 3,309,192, Col. 5, line 43 through Col. 7, line 62 and Examples 8,12,15,39,41, 52, 53, 58,132,138-140,162-164, 166, 167 and 169-182; U.S. 2,891,855, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pp 81-96; and Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific
35 Publications, Oxford, 1989. .
In the following Examples, all percentages are by weight and all formulations are prepared in conventional ways. Compound numbers refer to compounds in Index Tables A.
WO 01/70671 PCT/US01/09338
Example A Wettable Powder
Compound 1 65.0%
dodecylphenol polyethylene glycol ether 2.0%
5 sodium ligninsulfonate 4.0%
sodium silicoaluminate 6.0%
montmoriUonite (calcined) 23.0%.
Example B
Granule
10 Compound 1 10.0%
attapulgite granules (low volatile matter,
0.71/0.30 mm; U.S.S. No. 25-50 sieves) 90.0%.
Example C Extruded Pellet
15 Compound 1 25.0%
anhydrous sodium sulfate 10.0%
crude calcium Hgninsulfonate 5.0%
sodium allcylnaphmalenesulfonate 1.0%
calcium/magnesium bentonite 59.0%.
20 Example D
Emulsifiable Concentrate
Compound 1 20.0%
blend of oil soluble sulfonates
and polyoxyethylene ethers 10.0%
25 isophorone 70.0%.
The compounds of this invention exhibit activity against a wide spectrum of foliar-feeding, -fruit-feeding, stem or root feeding, seed-feeding, aquatic and soil-inhabiting arthropods (term "arthropods" includes insects, mites and nematodes) which are pests of growing and stored agronomic crops, forestry, greenhouse crops, ornamentals, nursery crops, 30 stored food and fiber products, livestock, household, and public and animal health. Those skilled in the art will appreciate that not all compounds are equally effective against all growth stages of all pests. Nevertheless, all of the compounds of this invention display activity against pests that include: eggs, larvae and adults of the Order Lepidoptera; eggs, foliar-feeding, fruit-feeding, root-feeding, seed-feeding larvae and adults of the Order 35 Coleoptera; eggs, irnmatures and adults of the Orders Hemiptera and Homoptera; eggs,' larvae, nymphs and adults of the Order Acari; eggs, irnmatures and adults of the Orders Thysanoptera, Orthoptera and Dermaptera; eggs, irnmatures and adults of the Order Diptera;
WO 01/70671 PCT/US01/09338
and eggs, juveniles and adults of the Phylum Nematoda. The compounds of this invention are also active against pests of the Orders Hyrnenoptera, Isoptera, Siphonaptera, Blattaria, Thysanura and Psocoptera; pests belonging to the Class Arachnida and Phylum Platyhekrrinthes. Specifically, the compounds are active against southern com rootworm 5 (Diabrotica undecimpunctata howardi), aster leafhopper (Mascrostelesfascifrons), boll
weevil (Anthonomus grandis), two-spotted spider mite (Tetranychus urticae), fall armyworm (Spodopterafrugiperda), black bean aphid (Aphis fabae), green peach aphid (Myzus persica), cotton aphid (Aphis gossypii), Russian wheat aphid (Diuraphis noxia), English grain aphid (Sitobion avenae), whitefly (Bemisia tabacif), tobacco budworm (Heliothis
10 virescens), rice water weevil (Lissorhoptrus oryzophilus), rice leaf beetle (Oulema oryzae), whitebacked planthopper (Sogatellafurciferd), green leafhopper (Nephotettix cincticeps), brown planthopper (Nilaparvata lugens), small brown planthopper (LaodeJphax striatellus), rice stem borer (Chilo suppressalis), rice leafroller (Cnaphalocrocis medinalis). black rice stink bug (Scotinophara lurida), rice stink bug (Oebalus pugnax), rice bug (Leptocorisa
15 chinensis), slender rice bug (Cletuspuntiger), southern green stink bug (Nezara viridula) and german cockroach (Blatella germanicd). The compounds are active on mites, demonstrating ovicidal, larvicidal and chemosterilant activity against such families as Tetranychidae including Tetranychus urticae, Tetranychus cinnabarinus, Tetranychus mcdanieli, Tetranychus pacificus, Tetranychus turkestani, Byrobia rubrioculus, Panonychus ulmi,
20 Panonychus citri, Eotetranychus carpini borealis, Eotetranychus, hicoriae, Eotetranychus sexmaculatus, Eotetranychus yumensis, Eotetranychus banksi and Oligonychus pratensis; Tenuipalpidae including Brevipalpus lewisi, Brevipalpus phoenicis, Brevipalpus californicus and Brevipalpus obovatus; Eriophyidae including Phyllocoptruta oleivora, Eriophyes sheldoni, Aculus cornutus, Epitrimerus pyri and Eriophyes mangiferae. See WO 90/10623
25 and WO 92/00673 for more detailed pest descriptions.
Compounds of this invention can also be mixed with one or more other insecticides, fungicides, nematocides, bactericides, acaricides, growth regulators, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants or other biologically active compounds to form a multi-component pesticide giving an even broader spectrum of
30 agricultural protection. Examples of such agricultural protectants with which compounds of this invention can be formulated are: insecticides such as abamectin, acephate. avermectin, azinphos-methyl, bifenthrin, buprofezin, carbofuran, chlorfenapyr, chlorpyrifos, chlorpyrifos-methyl, clothianidin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, cypermethrin, deltamethrin, diafenthiuron, diazinon, diflubenzuron,
35 dimethoate, diofenolan, emamectin, endosulfan, esfenvalerate, fenothiearb, fenoxycarb, fenpropathrin, fenvalerate, fipronil, flucythrinate, tau-fluvalinate, flufendxuron, fonophbs, imidacloprid, isofenphos, malathion, metaldehyde, methamidophos, methidathion, methomvl. methonrene. methoxvchlor. methvl 7-chloro-2,5-dihydro-2-[[AT-
WO 01/70671 PCT/US01/09338
(methoxycarbonyl)-^-^
(tiMuorometboxy)phenyl]aii)ino]carbonyl]iiideno[l ,2-e][l ,3,4]oxadkzine-4a(3#)-carboxylate (mdoxacarb),'monocrotophos, oxamyl, parathion, paratbion.-metb.yl, permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos, pymetrozine, 5 pyriproxyphen, rotenone, spionsad, sulprofos, tebufenozide, tefluthrin, terbufos, tetraGhlorvinphos, thiacloprid, tbiodicarb, tralomethrin, trichlorfon and triflumuron; fungicides such, as acibenzolar, azoxystrobin, benomyL, blasticidin-S, Bordeaux mixture (Tribasic copper sulfate), bromuconazole, carpropamid (KTU 3616), captafol, captan, carbendazun, chloroneb, chlorothalonil, copper oxychloride, copper salts, cymoxanil,
10 cyproconazole, cyprodinil (CGA 219417),(1S)-3,5-dichloro-iV-(3H;hloro-l-ethyl-l-methyl- 2-oxopropyl)-4-metiiylbenzamide (RH 7281), diclocymet (S-2900), diclomezine, dicloran, difenoconazole5(S)-3,5-aUhydro-5-memyl-2-(methyltHo)-5-phenyl~3-(phenylamino)-4i?-imidazol-4-one (RP 407213), dimethomorph, diniconazole, diniconazole-M, dodine, edifenphos, epoxiconazole (BAS 480F), famoxadone, fenamidone, fenarimol,
15 fenbuconazole, fencaramid (SZX0722), fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, fluazJnam, fludioxonil, flumetover (RPA 403397), fluquinconazole, flusilazole, flutolanil, flutriafol, folpet, fosetyl-aluminum, furalaxyl, furametapyr (S-82658), hexaconazole, ipconazole, iprobenfos, iprodione, isoprothiolane, kasugamycin, kresoxim-methyl, mancozeb, maneb, mefenoxam, mepronil, metalaxyl,
20 metconazole, metommostrobin/fenoniinostrobin (SSF-126), myclobutanil, neo-asozin (ferric methanearsonate), oxadixyl, penconazole, pencycuron, probenazole, prochloraz, propamocarb, propiconazole, pyrifenox, pyraclostrobin, pyrimethanil, pyroquilon, quinoxyfen, spiroxamine, sulfur, tebuconazole, tetraconazole, thiabendazole, thifiuzamide, thiophanate-methyl, thiram, triadimefon, triadimenol, tricyciazole, trifioxystrobin,
25 triticonazole, .validamycin and vinclozolin; nematocides such as aldicarb, oxamyl and
fenamiphos; bactericides such as streptomycin; acaricides such as amitraz, chinornethionat, chlorobenzilate, cyhexatin, dicofol, dienochlor, etoxazole, fenazaquin, fenbutatin oxide, fenpropathrin, fenpyroximate, hexythiazox, propargite, pyridaben and tebufenpyrad; and biological agents such as Bacillus thuringiensis, Bacillus thicringiensis delta endotoxin,
30 . baculovirus, and entomopathogenic bacteria, virus and fungi.
Preferred insecticides and acaricides for mixing with compounds of this invention include pyrethroids such as cypeimethrin, cyhalothrin, cyflufbrin and beta-cyfluthrin, esfenvalerate, fenvalerate and tralomethrin; carbamates such as fenothicarb, methomyl, oxamyl and thiodicarb; neonicotinoids such as clothianidin, imidacloprid and thiacloprid,
35 neuronal sodium channel blockers such as indoxacarb, insecticidal macrocyclic lactones such as spinosad, abamectin, avermectin and emamectin; GAB A antagonists such as endosulfan and fipronil; insecticidal ureas such as flufenoxuron and triflumuron, juvenile hormone mimics such as diofenolan and pyriproxyphen; pymetrozine; and amitraz.
WO 01/70671 PCT/US01/09338
Preferred biological agents for mixing with compounds of this invention include Bacillus thuringiensis and Bacillus tkuringiensis delta endotoxin.
, Most preferred mixtures include a mixture of a compound of this invention with cyhalothrin; a mixture of a compound of this invention with beta-cyfluthrin; a mixture of a 5 compound of this invention with esfenvalerate; a mixture of a compound of this invention with methomyl; a mixture of a compound of this invention with imidacloprid; a mixture of a compound of this invention with thiacloprid; a mixture of a compound of this invention with indoxacarb; a mixture of a compound of this invention with abamectin; a mixture of a compound of this invention with endosulfan; a mixture of a compound of this invention with
10 fipronil; a mixture of a compound of this invention with flufenoxuron; a mixture of a
compound of this invention with pyriproxyphen; a mixture of a compound of this invention with; a mixture of a compound of this invention with pymetrozine; a mixture of a compound of this invention with amitraz; a mixture of a compound of this invention with Bacillus thuringiensis and a mixture of a compound of this invention with Bacillus thuringiensis delta
15 endotoxin.
In certain instances, combinations with other arthropodicides having a similar spectrum of control but a different mode of action will be particularly advantageous for resistance management.
Arthropod pests are controlled and protection of agronomic, horticultural and
20 specialty crops, animal and human health is achieved by applying one or more of the . compounds of this invention, in an effective amount, to the environment of the pests including the agronomic and/or nonagronomic locus of infestation, to the area to be protected, or directly on the pests to be controlled. Thus, the present invention further comprises a method for the control of foliar and soil inhabiting arthropods and nematode
25 pests and protection of agronomic and/or nonagronomic crops, comprising applying one or more of the compounds of the invention, or compositions containing at least one such compound, in an effective amount, to the environment of the pests including the agronomic and/or nonagronomic locus of infestation, to the area to be protected, or directly on the pests to be controlled. A preferred method of application is by spraying. Alternatively, granular
30 formulations of these compounds can be applied to the plant foliage or the soil. Other methods of application include direct and residual sprays, aerial sprays, seed coats, microencapsulations, systemic uptake, baits, eartags, boluses, foggers, fumigauts, aerosols, dusts and many others. The compounds can be incorporated into baits that are consumed by-the arthropods or in devices such as traps and the like.
3 5 The compounds of this invention can be applied in their pure state, but most often
application will be of a formulation comprising one or more compounds with suitable carriers, diluents, and surfactants and possibly in combination with a food depending on the contemplated end use. A preferred method of application involves spraying a water
WO 01/70671 PCI7US01/09338
dispersion or refined oil solution of the compounds. Combinations with spray oils, spray oil
concentrations, spreader stickers, adjuvants, other solvents, and synergists such as piperonyl
butoxide often enhance compound efficacy. The rate of application required for effective control will depend on such factors as 5 the species of arthropod to be controlled, the pest's life cycle, life stage, its size, location, time of year, host crop or animal, feeding behavior, mating behavior, ambient moisture, temperature, and the like. Under normal circumstances, application rates of about 0.01 to 2 kg of active ingredient per hectare are sufficient to control pests in agronomic ecosystems, but as little as 0.001 kg/hectare may be sufficient or as much as 8 kg/hectare may be
10 required. For nonagronomic applications, effective use rates will range from about 1.0 to 50 mg/square meter but as little as 0.1 mg/square meter may be sufficient or as much as 150 mg/square meter may be required.
The following TEST demonstrates the control efficacy of compounds of tins invention on specific pests. "Control efficacy" represents inhibition of arthropod
15 development (including mortality) that causes significantly reduced feeding. The pest
control protection afforded by the compounds is not limited, however, to these species. See Index Tables A through Q for compound descriptions. The following abbreviations are used in the Index Tables which follow: t is tertiary, n is normal, i is iso, c is cyclo, s is secondary, Me is methyl, Et is ethyl, Pr is propyl, i-Pr is isopropyl, c-Pr is cyclopropyl, Bu is butyl, s-
20 Bu is secondary butyl, Pent is pentyl, OMe is methoxy, OEt is ethoxy, SMe is methylthio, SEt is ethylthio, CN is cyano, N02 is nitro, and Het is heterocycle. The abbreviation "Ex." stands for "Example" and is followed by a number indicating in which example the compound is prepared.
25
B is O, except where indicated
Compound R1 R2 R3 R4 Rs and/or R6 m.p. °C
l(Exl) H i-Pr H 2-Me 4-OCF3 . 207-209

WO 01/70671 PCT/US01/09338

a 1H NMR data are in ppm downfield from tetramethylsilane. Couplings are designated by (s)-singlet,
(d)-doublet, (t)-triplet, (q)-quartet, (m)-multiplet, (dd)-doublet of doublets, (dt)~doiiblet of triplets,
(br s)-broad singlet. .
BIOLOGICAL EXAMPLES OF THE INVENTION
TEST Application: Compounds are formulated in a 10% acetone, 90% water and 300 ppm X-77 surfactant solution, unless otherwise indicated. The formulated compounds are applied 5 with a SUJ2 atomizer nozzle with 1/8 JJ custom body (Spraying Systems) positioned Vi' above the top of each test unit There are 6 of these nozzles that make up the spray boom and this is fixed in a belt sprayer. A rack (or carrier) of 6 different insect test units is placed on the conveyor belt and stops so that each unit is centered under a nozzle. Once the rack is centered, 1 mL of liquid is sprayed into each test unit; the rack then continues down the belt 10 to the end of the sprayer to be off-loaded. All experimental compounds in this screen are sprayed at 250 ppm and replicated three times.
Diamondback Moth (DBM) - Plutella Xylostella: The test unit consists of a small self-contained unit with a 12-14 day old radish plant inside. These are pre-infested (using a core sampler) with 10-15 neonate larvae on apiece of insect diet. Once 1 mL of formulated 15 compound has been sprayed into each test unit, the test units are allowed to dry for 1 hour before a black, screened cap-is placed on the top of the cylinder. They are held for 6 days in a growth chamber at 25 °C and 70% relative humidity.
Plant feeding damage was visually assessed on a scale of 0-10 where 0 is no feeding, 1 is 10% or less feeding, 2 is 20% or less feeding, 3 is 30% or less feeding through a 20 maximum score of 10 where 10 is 100% of foliage consumed. Of the compounds tested the following provided excellent levels of plant protection (ratings of 0-1,10% or less feeding damage): 1,2, 3,4, 6,7,9,10,13,14,15,19,20,24, 27,28,29, 30,31,32, 33, 35,' 37,38, 39, 51, 52, 53, 60, 61, 62, 63, 64, 65,66, 68, 69, 72,73, 74, 75,76, 79, 80, 84, 86, 88, 89,90,

WO 01/70671 PCT/US01/09338
^ 92,96, 97,98,99,100,101,102,103,107,113,124,126,127,143,144,146,147,148,150, 151,152,153,158,159,160,161,162,16.3,164,165,166,167,169,170,171,174,183, 184,185, 186,187,188,189,190,191,193,194,195,196,198,202,203,204,205,206, 207,208, 209,210,211,212,213,214,215,216,217,218,219,220,222,223,225,227, ' 5 228,229, 230,231,232,233,235,238,239,240,244,245,246,248,249,250,251,252, 253,256, 257,275,276,277,278, B2, B4, B5, B6, B7, B8, B9, BIO, Bll, B12, B13, B14, B15, B16, B17, B18, B19, B20, B21, B23, B24, B25, B28, B29, B30, B31, B32, B33, B35, B37, B38, B39, B40, B42, B43, B44, B45, B46, B47, B48, B49, B50, B53, B55, B57, B58, B59, B60, B61, B62, B63, B64, B66, B67, B68, B69, B70, B71, B72, B74, B75, B76, CI, 10 C2, C3, C4, C5, C7, C8, C9, CIO, CI 1, C12, C79, D2, D3,D4, D5, D6, D7, D8, Dll, D12, D13, D14, D15, D16, D18, D19, D20, D23, D24, D25, D26, D27, D28, D29, D30, D32, D33, D34, D37, D38, D39, D40, D41, D42, D45, D46, D47, D48, D50, D51, D52/D53, D54, D55, D56, D57, D58, D59, D60, D61, D62, D63, D64, D65, D66, D67, D68, D69, D70, D71, D72, D73, D74, D75, D76, D77, D78, D79, D81, D83, D84, D85, D86, D87, 15 D88, D89, D91, D92, D93, D94, D95, D96, D97, Dill, D113, D114, D115, D116, D117, D118, D119, D120, D121, D122, D123, D124, D125, D126, D162, D164, E4, F2, F5, F6, F7, F8, G2, G3, G5, HI, H2, H3, H4, J3, J4,16, Ml, M3, N2 and PL

We claim:
1. A method for controlling arthropods comprising contacting the arthropods 01 their environment with an arthropodicidally effective amount of a compound of Formula 1, its TV-oxide or agriculturally suitable salts

wherein
A and B are independently 0 or S;
each J is independently a phenyl or naphthyl group substituted with 1 to 2 R-"" and optionally substituted with 1 to 3 R6;
or each J is independently a 5- or 6-membered heteroaromatic ring or an aromatic 8-, 9- or I O-membered fused heterobicyclic ring system wherein-each ring or ring system is optionally substituted with 1 to 4 R7;
n is 1 to 4,
R1 is H; or CrC() alkyl, C2-C6 alkenyl, C2-C6 alkynyl or C3~C6 cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, N02, hydroxy. CrC4 alkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C[-C4 alkylsulfonyl, C2~C4 alkoxycarbonyl, CpC4 alkylamino. C2-C^ dialkylamino and C^-C^, cycloalkylamino; or
R1 is C2-Q, alkylcarbonyl, C2-C(y alkoxycarbonyl, C2-CV> alkylaminocarbonyl. CrC8 dialkylaminocarbonyl or C(=A)J;
R2 is H, C,-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, CrC4 alkoxy, C\-C+ alkylamino, C2-Cx dialkylamino, C^-Q, cycloalkylamino. C2-C6 alkoxycarbonyl or C2-C6 alkylcarbonyl;
R3 is H; G; CrC6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-Cf) cycloalkyl, each optionally substituted with one or more substituents selected from the group consisting of halogen, G, CN, N02, hydroxy, CrC4 alkoxy, CrC4 haloalkoxv, C y-C j,alkylthio, Ci,-C4alkylsulfinyl. Gj^C^alkylsulfonyL CrC^

alkoxycarbonyl, C2-C6 alkylcarbonyl, C3-C6 trialkylsilyl, and a phenyl, phenoxy or 5- or 6-membered heteroaromatic ring, each ring optionally substituted with one to three substituents independently selected from the group consisting of CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, CrC4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyi, halogen, CN, NO2, C1-C4 alkoxy, C1-C4 haloalkoxy, CpC4 alkylthio, CrC4 alkylsulfinyl, CpC4 alkylsulfonyl, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C3-C6 (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl and C3-Q3 trialkylsilyl; Q-C4 alkoxy; Ci-C4 alkylamino, C2-C8 dialkylamino; C3-Q, cycloalkylamino; C2-C^ alkoxycarbonyl or C2-Q, alkylcarbonyl; or R2 and R' can be taken together with the nitrogen to which they are attached to form a ring containing 2 to 6 atoms of carbon and optionally one additional atom o\' nitrogen, sulfur or oxygen, said ring may be optionally substituted with 1 to 4 substituents selected from the group consisting of Ci-C2 alkyl, halogen. CN, N02 and C1-C2 alkoxy; G is a 5- or 6-membered nonaromatic carbocyclic or heterocyclic ring, optionally including one or two ring members selected from the group consisting of C( 0). SO or S(0)2 and optionally substituted with 1 to 4 substituents selected from the group consisting of Ci-C2 alkyl, halogen, CN, N02 and Cj-C2 alkoxy. each R~* is independently H, Cj-Q, alkyl, C2-C
C2-C6 alkoxycarbonyl, C2-Cg alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl or C3-C6 trialkylsilyl; each R5 is independently CrC6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, CrC6 halocycloalkyl, CN, N02, CrC4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, C1-C4 alkylsulfonyl, C!-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, Cj-C6 haloalkylsulfonyl, Ci-C4 alkylamino, C2-Cs dialkylamino, or CrC6 cycloalkylamino, C2-C6 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, or C3-C8 dialkylaminocarbonyl; or (fl5)2 when attached to adjacent carbon atoms can be taken together as -OCF20-,
-CF2CF20-. or -OCF2CF20-; each R6 is independently H, halogen, Cj-Q, alkyl. C2-Cr) alkenyl, C2-C6 alkynyl,
C3-C(j cycloalkyl, Ct-C4 alkoxy or C2-C4 alkoxycarbonyl; or each R6 is independently a phenyl, benzyl, phenoxy. 5- or 6-membered heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system, each ring optionally substituted with one to three substituents independently selected from the group consisting of CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, CrC6 cycloalkyl, C,-C4 haloalkyl, C2-C4 haloalkenyl. C2-C4 haloalkynyl, CyC() halocycloalkyl, halogen, CN. N02, CrC4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl. Ci-C4 alkylsulfonyl, C|-C4 alkylamino, C2-C8 dialkylamino, CyCb cycloalkylamino, C^-CV, (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl. C2-Cf, alkoxycarbonyl, C2-C6 alkylaminocarbonyl, CyC$ dialkylaminocarbonyl and CrCG trialkylsilyl; each R7 is independently H, C]-Cf) alkyl, C2-CG alkenyl, C2-C^ alkynyl, CyC(, cycloalkyl. CrC6 haloalkyl, C2-C6 haloalkenyl, C2-C(, haloalkynyl. CyC() halocycloalkyl, halogen, CN, C02H, CONH2, N02, hydroxy, CrC4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, CrC4 alkylsulfonyl, CrC4 haloalkylthio, C|-C4 haloalkylsulfinyl, C|-C4 haloalkylsulfonyl, C]-C4 alkylamino, C2-Cg dialkylamino, CyC() cycloalkylamino, C2-C6 alkylcarbonyl, C2-Cf) alkoxycarbonyl, C2-Cf) alkylaminocarbonyl, C_--Cg dialkylaminocarbonyl, or C^-Q, trialkylsilyl. or each R7 is independently a phenyl, benzyl, benzoyl, phenoxy, 5- or 6-membered heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system, each ring optionally substituted with one to three substituents independently selected from the group consisting of CpC4 alkyl,

C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, CrC4 haloalkyl, C2-C4
haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, N02,
CrC4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, Cr
C4 alkylsulfonyl, CrC4 alkylamino, C2-C8 dialkylamino, C3-C6
cycloalkylamino, C3-C6 (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-C6
alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl and
C3-C provided that
J is other than an optionally substituted 1,2,3-thiadiazole.
2. The method as claimed in 1 wherein J is a phenyl group substituted with I to
2 R5 and optionally substituted with 1 to 3 R6
3. The method as claimed in 2 wherein
A and B are both O.
n is 1 to 2;
R1 is H, C,-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-Cf, cycloalkyl, C2-C„
alkylcarbonyl or C2-Q, alkoxycarbonyl; R2 is H, CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, CrC6
alkylcarbonyl or C2-Cf, alkoxycarbonyl; R3 is C|-Cc alkyl. C2-Q, alkenyl, C2-Q, alkynyl or C3-C(j cycloalkyl each
optionally substituted with one or more substituents selected from the group
consisting of halogen, CN, Cj-C2 alkoxy, Cj-C2 alkylthio, CpC2
alkylsulfinyl and Cj-C2 alkylsulfonyl; one of the R4 groups is attached to the phenyl ring at the 2-position or 5-position,
and said R4 is C,-C4 alkyl, CrC4 haloalkyl, halogen, CN, N02, CrC4
alkoxy, CpC4 haloalkoxy, Cj-C4 alkylthio, C)-C4 alkylsulfinyl, Cj-C4
alkylsulfonyl, Cj-C4 haloalkylthio, CpC4 haloalkylsulfinyl, or CpC4
haloalkyl sulfonyl; each R5 is independently C^-C^ haloalkyl, CN, N02, CrC4 haloalkoxy, CrC4
alkylthio. C\-C^ alkylsulfinyl, C|-C4 alkylsulfonyl, Cj-C4 haloalkylthio, Cp
C4 haloalkylsulfinyl, C|-C4 haloalkylsulfonyl or C2-C4 alkoxycarbonyl; or (R-"02 when attached to adjacent carbon atoms can be taken together as -OCFTO-,
-CF2CF20- or -OCF2CF20-; and each R6 is independently H, halogen, Ct-C4 alkyl, CpC2 alkoxy or C2-C4
alkoxycarbonyl, or each R6 is independently a phenyl or a 5- or 6-membered heteroaromatic ring, each
ring optionally substituted with CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl.

c3-c6 cycloalkyl, CrC4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, N02, C1-C4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio, C1-C4 alkylsulfinyl, CrC4 alkylsulfonyl, CrC4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C3-C6 (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-CG alkylaminocarbonyt, C3-C8 dialkylaminocarbonyl or C3-C6 trialkylsilyl.
4. The method as claimed in 3 wherein
Rl and R2 are both H;
R3 is CrC4 alkyl optionally substituted with halogen, CN, OCH3, or S(0)pCH3;
each R4 is independently H, CH3, CF3, OCF3, OCHF2, S(0)pCF3, S(0)pCHF2. CN or halogen;
each R5 is independently CF3, OCF3, OCHF2, S(0)pCF3, S(0)pCHF2. OCH:CF3, OCF2CHF2. S(0)pCH2CF3 or S(0)pCF2CHF2;
each R6 is independently H, halogen or methyl; or phenyl, pyrazole, imidazole, triazole. pyridine or pyrimidine, each ring optionally substituted with C1-C4 alkyl, C1-C4 haloalkyl, halogen or CN; and
p is 0, 1 or 2.
5. The method as claimed in 4 wherein R3 is /-propyl or /-butyl.
6. The method as claimed in 1 wherein J is a 5- or 6-membered heteroaromatic ring optionally substituted with 1 to 4 R7.
7. The method as claimed in 6 wherein
.1 is a 5- or 6-membered heteroaromatic ring selected from the group consisting of J-l, J-2. J-3. J-4 and J-5, each J optionally substituted with 1 to 3 R7

Q is O, S or NRT; and

W, X, Y and Z are independently N or CR7, provided that in J-4 and J-5 at least one
ofW, X,YorZisN. 8. The method as claimed in 6 or 7 wherein A and B are O;
n is 1 to 2;
R1 is H, CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C2-C6 alkylcarbonyl or C2-C6 alkoxycarbonyl;
R2 is H, CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C2-C6 alkylcarbonyl or C2-C(j alkoxycarbonyl;
R^1 is H; or CrCfi alkyl, C2-Cr, alkenyl, C2-C6 alkynyl or CrC6 cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, C|-C2 alkoxy, C[-C2 alkylthio, CpC2 alkylsulfinyl and C|-C2 alkylsulfonyl;
one of the R4 groups is attached to the phenyl ring at the 2-position, and said R4 is C,-C4 alkyl, C,-C4 haloalkyl, halogen, CN, N02, CrC4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, CrC4 alkylsulfonyl, CrC4 haloalkylthio, CrC4 haloalkylsulfinyl or CpQ haloalkylsulfonyl; and
each R7 is independently H, CrC4 alkyl, CrC4 haloalkyl, halogen, CN, N02, Cr C4 haloalkoxy, C\-C^ alkylthio, CrC4 alkylsulfinyl, CrC4 alkylsulfonyl, CrC4 haloalkylthio, CrC4 haloalkylsulfinyl, CpC4 haloalkylsulfonyl or C2-C4 alkoxycarbonyl; or a phenyl or a 5- or 6-membered heteroaromatic ring, each ring optionally substituted with C]-C4 alkyl, C2-C4 alkenyl. C2-C4 alkynyl, CrQ, cycloalkyl, CrC4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, CrC6 halocycloalkyl, halogen, CN, N02, C,-C4 alkoxy, C,-C4 haloalkoxy. C,-C4 alkylthio, CrC4 alkylsulfinyl, C,-C4 alkylsulfonyl, C,-C4 alkylamino, C2-Cg dialkylamino, C^-C^ cycloalkylamino, C^-C^ (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-Cf, alkoxycarbonyl, C2-Cf, alkylaminocarbonyl, C^-C^ dialkylaminocarbonyl or C3-Q-, trialkylsilyl.
9. The method as claimed in 8 wherein J is selected from the group consisting of pyridine, pyrimidine, pyrazole, imidazole, triazole, thiophene, thiazole and oxazole, furan, isothiazole and isoxazole, each optionally substituted with 1 to 3 R7.
10. The method as claimed in 9 wherein
J is selected from the group consisting of pyridine, pyrimidine, pyrazole, thiophene
and thiazole, each optionally substituted with 1 to 3 R7; R1 and R2 are both H; R?1 is C,-C4 alkyl optionally substituted with halogen, CN, OCH3, or S(0)pCH3;

each R4 is independently H, CH3) CF3, OCF3, OCHF2, S(0)pCF3, S(0)pCHF2, CN or halogen;
each R7 is independently H, halogen, CH3, CF3, OCHF2, S(0)pCF3, S(0)pCHF2, OCH2CF3. OCF2CHF2, S(0)pCH2CF3, S(0)pCF2CHF2; or phenyl, pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted with C,-C4 alkyl, C,-C4 haloalkyl, CrC4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, CrC4 alkylsulfonyl, halogen or CN; and
p is 0, 1 or 2.
11 The method as claimed in 10 wherein J is a pyridine optionally substituted with I to 3 R12. The method as claimed in 11 wherein one R7 is a phenyl optionally substituted with C|-C4 alkyl, CrC4 haloalkyl, halogen or CN.
13. The method as claimed in 11 wherein one R7 is a pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted with Cj-C4 alkyl, C|-C4 haloalkyl, halogen or CN.
14. The method as claimed in 10 wherein J is a pyrimidine optionally substituted with 1 to 3 R7.
15. The method as claimed in 14 wherein one R7 is a phenyl optionally substituted with C|-C4 alkyl, CrC4 haloalkyl, halogen or CN.
16. The method as claimed in 14 wherein one R7 is a pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted with C]-C4 alkyl. C(-C4 haloalkyl, halogen or CN

17. The method as claimed in 10 wherein J is a pyrazole optionally substituted with 1 to 3 R7
18. The method as claimed in 17 wherein one R7 is a phenyl optionally substituted with C\-C+ alkyl, C|-C4 haloalkyl, halogen or CN.
19. The method as claimed in 17 wherein one R7 is a pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted with CpC4 alkyl, CpC4 haloalkyl, halogen or CN.
20. The method as claimed in 19 wherein R7 is a pyridine optionally substituted with C |-C4 alkyl, C i-C4 haloalkyl. halogen or CN
21. The method as claimed in 1 comprising a compound of Formula 1 selected from the group consisting of:
3-methyl-A'-( l-methylethyl)-2-[[4-(trifluoromethyl)benzoyl]amino]-benzamide,
2-methyl-A*-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-4-
(trifluoromethyl)benzamide.

2-methyl-JV-[2-methyl-6-[[(l-methylethyI)amino]carbonyl]phenyl]-6-
(trifluoromethyl)-3-pyridinecarboxamide,
\ -ethyl-N-[2-methyl-64[( 1 -methylethyl)amino]carbonyl]phenyl}-3 -
(trifluoromethyl)-l//-pyrazoIe-5-carboxamide,
l-(2-fluorophenyl)-A^-[2-methyl-6-[[(l-methylethyl)amino)carbonyl]phenyl]-3-
(trifluoromethyl)-l//-pyrazole-5-carboxarnide, 1 -(3-chloro-2-pyridinyl)-A42-methyl-6-[[(l -
methylethyl)amino]carbonyl]phenyl]3-(trifluoromethyl)-l/f-pyrazole-5-carboxamide,
A^-[2-chloro-6-[[(l-methylethyl)amino]carbonyl]phenyl]-l-(3-chloro-2-pyridinyl)-3-(trit1uoromethyl)-l//-pyrazoIe-5-carboxamide, 3-bromo-1 -(2-chlorophenyl)-A^-[2-methyl-6-[[( 1 -methylethyl)amino]carbonyl]phenyl]-l//-pyrazole-5-carboxamide, and 3-bromo-A-[2-chloro-6-[[(l-niethylethyl)amino]carbonyl]phenyl]-l-(2-chlorophenyl)-l//-pyrazole-5-carboxamide. 22. A compound of Formula \, its N-oxides and agriculturally suitable salts

wherein
A and B are independently O or S;
each J is independently a phenyl or naphthyl group substituted with 1 to 2 R-"* and
optionally substituted with 1 to 3 R6;
or each J is independently a 5- or 6-membered heteroaromatic ring or an aromatic
8-,c)- or 10-membered fused heterobicyclic ring system wherein each ring or
ring system is optionally substituted with 1 to 4 R7; n is 1 to 4; R1 is H; or Cj-C(- alkyl, C2-Q alkenyl, C2-Q, alkynyl or C^-Cc cycloalkyl each
optionally substituted with one or more substituents selected from the group

consisting of halogen, CN, N02, hydroxy, CrC4 alkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, CrC4 alkylsulfonyl, C2-C4 alkoxycarbonyl, CrC4 alkylamino, C2-C8 dialkylamino and C3-C6 cycloalkylamino; or
R1 is C2-C6 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C R2 is H, CrC6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, CrC4 alkoxy, CrC4 alkylamino, C2-C8 dialkylamino, C3-C R3 is H; CrC6 alkyl, C2-CG alkenyl, C2-C6 alkynyl, CrC optionally substituted with one or more substituents selected from the group consisting of halogen, CN, N02, hydroxy, C1-C4 alkoxy, C[-C4 haloalkoxy, C,-C4 alkylthio. C,-C4 alkylsulfinyl, C,-C4 alkylsulfonyl, C2-C(, alkoxycarbonyl, C2-C(, alkylcarbonyl, C3-Q trialkylsilyl, and a phenoxy ring optionally substituted with one to three substituents independently selected from the group consisting of C)-C4 alkyl, C2-C4 alkenyl, C2~C4 alkynyl, Cy Cf, cycloalkyl. CrC4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, Cy C() halocycloalkyl, halogen, CN, N02, CpC4 alkoxy, Cj-C4 haloalkoxy, Cp C4 alkylthio. Cj-C4 alkylsulfinyl, Cj-C4 alkylsulfonyl, Cj-C4 alkylamino, Cj-C-x dialkylamino, CyC(} cycloalkylamino, C3-Cg (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-Cf, alkoxycarbonyl, C2-Q$ alkylaminocarbonyl, Cy Cs dialkylaminocarbonyl and CyC() trialkylsilyl; C]-C4 alkoxy; Cj-C4 alkylamino. C2-Cx dialkylamino; CyC(} cycloalkylamino; C2-C6 alkoxycarbonyl or C2-Q, alkylcarbonyl; or R2 and R-' can be taken together with the nitrogen to which they are attached to form a ring containing 2 to 6 atoms of carbon and optionally one additional atom of nitrogen, sulfur or oxygen, said ring may be optionally substituted with 1 to 4 substituents selected from the group consisting of CpC2 alkyl, halogen, CN. N02 and CrC2 alkoxy; each R4 is independently H, C.\-C,(i alkyl, C2-C6 alkenyl, C2-C(-, alkynyl, CyC() cycloalkyl. CrC(, haloalkyl, CrC6 haloalkenyl, C2-C6 haloalkynyl. CrC6 halocycloalkyl. halogen, CN, N02, hydroxy, CrC4 alkoxy, CrC4 haloalkoxy. CrCA alkylthio, C,-C4 alkylsulfinyl, CrC4 alkylsulfonyl, CrC4 haloalkylthio. CrC4 haloalkylsulfinyl, CrC4 haloalkylsulfonyl, CrC4 alkylamino. C2-Cg dialkylamino, CyC(y cycloalkylamino, or CyC^ trialkylsilyl: or

each R4 is independently phenyl, benzyl or phenoxy, each optionally substituted with CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, CrC4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, N02, CrC4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, Cj-C4 alkylsulfonyl, CrC4 alkylamino, C2-Cg dialkylamino, C3-C6 cycloalkylamino, C3-C6 (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-CG alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl or C3-C6 trialkylsilyl;
each R5 is independently Cj-Q, haloalkyl, C2-C.6 haloalkenyl, C2-C6 haloalkynyl, CrC6 halocycloalkyl, CrC4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, CrCi alkylsulfonyl, CrC4 haloalkylthio, C,-C4 haloalkylsulfinyl, CrC4 haloalkylsulfonyl, CN. N02, C|-C4 alkylamino. C2-Cs dialk\ lamino, C^-Q, cycloalkylamino, C2-Q alkylcarbonyl, C2-C() alkoxycarbonyl, C-rQ, alkylaminocarbonyl, or C3-C8 dialkylaminocarbonyl; or
(R^b attached to adjacent carbon atoms can be taken together as -OCF20-, -CF2CF:0-, or -OCF2CF20-;
each R6 is independently H, halogen, CpC^ alkyl, C2-C each R6 is independently a phenyl, benzyl, phenoxy. 5- or 6-membered heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system, each ring optionally substituted with one to three substituents independently selected from the group consisting of CpC4 alkyl, C2-C4 alkenyl, C2-C+ alkynyl, CrC6 cycloalkyl, CrC4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C(-) halocycloalkyl, halogen, CN, N02, CrC4 alkoxy, C,-C4 haloalkoxy, C^ alkylthio, C,-C4 alkylsulfinyl, CrC4 alkylsulfonyl, CrC4 alkylamino, C2-Cx dialkylamino, C3-Cf, cycloalkylamino, C3-Q, (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-Cf, alkoxycarbonyl, C2-C dialkylaminocarbonyl and C-?-Cf, trialkylsilyl;
each R7 is independently H, CpCf, alkyl, C2-Cf) alkenyl, C2-C(> alkynyl, C3-Cf) cycloalkyl. C|-Q, haloalkyl, C2-C6 haloalkenyl, C2-C(-) haloalkynyl, C-j-Q halocycloalkyl, halogen, CN, C02H, CONH2, N02, hydroxy, C,-C4 alkoxy, CrC4 haloalkoxy, C|-C4 alkylthio, CrC4 alkylsulfinyl, CrC4 alkylsulfonyl, CrC4 haloalkylthio, CrC4 haloalkylsulfinyl, CrC4 haloalkylsulfonyl, Cj-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C2-CG

alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl, or C3-C6 trialkylsilyl; or
each R7 is independently a phenyl, benzyl, benzoyl, phenoxy or 5- or 6-membered heteroaromatic ring or an 8-, 9- or 10-membered fused heterobicyclic ring system, each ring optionally substituted with one to three substituents independently selected from the group consisting of C]-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, CrC4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, N02, CrC4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfmyl, Cr C4 alkylsulfonyl, CrC4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C3-Q, (alkyl)cycloalkylamino. C2-C4 alkylcarbonyl. C2-C6 alkoxycarbonyl, C2-Q, alkylaminocarbonyl, CvCg dialkylaminocarbonyl and C3-Cc, trialkylsilyl;
provided that
(i) at least one R4 and at least one R7 are other than H:
(ii) J is other than an optionally substituted 1,2,3-thiadiazole;.
(iii) when J is an optionally substituted pyridine and R2 is H, R"1 is other than H or CH3;
(iv) when J is an optionally substituted pyridine, then R7 cannot be CONH2, C2-Cf, alkylaminocarbonyl or C^-C^ dialkylaminocarbonyl; and
(v) when J is an optionally substituted pyrazole, tetrazole or pyrimidine, then R2 and R-" cannot both be hydrogen.
23, The compound as claimed in 22 wherein J is a phenyl group substituted with
1 to 2 R? and optionally substituted with 1 to 3 R6.
24. The compound as claimed in 23 wherein
A and B are both 0;
n is 1 to 2;
R' is H, CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, CVC6
alkylcarbonyl or C2-C(, alkoxycarbonyl; R2 is H, C,-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl. C3-C6 cycloalkyl, C\-C6
alkylcarbonyl or C2-Cc, alkoxycarbonyl: R' is C\-C() alkyl. C2-Q, alkenyl, C2-CV, alkynyl or C3-Cf, cycloalkyl each
optionalK' substituted with one or more substituents selected from the group
consisting of halogen, CN, C)-C2 alkoxy, C]-C2 alkylthio, CpC?
alkylsulfmyl and C1-C2 alkylsulfonyl;

one of the R4 groups is attached to the phenyl ring at the 2-position Or 5-position, and said R4 is CrC4 alkyl, CrC4 haloalkyl, halogen, CN, N02, CrC4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio, Ci-C4 alkylsulfinyl, CrC4 alkylsulfonyl, CrC4 haloalkylthio, CrC4 haloalkylsulfinyl or CrC4 haloalkylsulfonyl;
each R5 is independently CrC4 haloalkyl, CN, N02, CrC4 haloalkoxy, CrC4 alkylthio. CrC4 alkylsulfinyl, CrC4 alkylsulfonyl, CrC4 haloalkylthio, Cr C4 haloalkylsulfinyl, CpC4 haloalkylsulfonyl or C2-C4 alkoxycarbonyl; or
(R-",)2 when attached to adjacent carbon atoms can be taken together as -OCF20-, -CF2CF20- or -OCF2CF20-; and
each R6 is independently H, halogen, C1-C4 aikyl, CpC2 alkoxy or C2-C4 alkoxycarbonyl, or
each R6 is independently a phenyl or.a 5- or 6-membered heteroaromatic ring, each ring optionally substituted with CpC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, CrC6 cycloalkyl, CrC4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-Q, halocycloalkyl, halogen, CN, N02, CpC4 alkoxy, Cj-C4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfinyl, CpC4 alkylsulfonyl, CpC4 alkylamino, C2-C8 dialkylamino, CrC6 cycloalkylamino, C3-C6 (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, Cr Cs dialkylaminocarbonyl or C^-C^ trialkylsilyl.
25 The compound as claimed in 24 wherein
R' and R2 are both H;
R' is CrC4 alkyl optionally substituted with halogen, CN, OCH3, or S(0)pCH3;
each R4 is independently H, CH3, CF3, OCF3, OCHF2, S(0)pCF3, S(0)pCHF2, CN or halogen;
each R5 is independently CF3, OCF3, OCHF2, S(0)pCF3, S(0)pCHF2. OCH2CF3, OCF2CHF2, S(0)pCH2CF3 or S(0)pCF2CHF2;
each Rf) is independently H, halogen or methyl; or phenyl, pyrazole, imidazole, triazole. pyridine or pyrimidine, each ring optionally substituted with C)-C4 alkyl, C j-C4 haloalkyl, halogen or CN; and p is 0, I or 2
2d The compound as claimed in 25 wherein R^ is /-propyl or /-butyl.
27 The compound as claimed in 22 wherein J is a 5- or 6-membered heteroaromatic ring optionally substituted with 1 to 4 R7.
28. The compound as claimed in 27 wherein

J is a 5- or 6-membered heteroaromatic ring selected from the group
consisting of J-l, J-2, J-3, J-4 and J-5, each J optionally substituted with 1 to 3 R7

QisO, SorNR7;and
VV, X, Y and Z are independently N or CR~. provided that in J-4 and J-5 at least one
ofW, X, YorZisN. 29. The compound as claimed in 27 or Claim 28 wherein
A and B are O;
n is 1 to 2;
R1 is H, C|-C4 alky I, Cj-C.^ alkenyl, C2-C4 alkynyl, C2-C6 alkylcarbonyl or C2-Q, alkoxycarbonyl;
R2 is H, C,-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, CrC6 cycloalkyl. C:-C(, alkylcarbonyl or C2-C(, alkoxycarbonyl.
R^ is H; or C(-C6 alkyl, C2-Q, alkenyl, C2-C{, alkynyl or C3-Q, cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen. CN, C|-C2 alkoxy, C]-C2 alkylthio, CpC2 alkylsulfinyl and C)-C2 alkylsullbnyl;
one of the R4 groups is attached to the phenyl ring at the 2-position, and said R4 is CrC4 alkyl, C|-C4 haloalkyl, halogen. CN, N02, C,-C4 alkoxy, CrC4 haloalkoxy, CpC4 alkylthio, C)-C4 alkylsulfinyl, C|-C4 alkylsulfonyl, C[-C4 haloalkylthio, C|-C4 haloalkylsulfinyl or C|-C4 haloalkylsulfonyl; and
each R7 is independently II, C|-C4 alkyl, CrC4 haloalkyl, halogen, CN, N02, C\-C4 haloalkoxy, C|-C4 alkylthio, C]-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, CrC^ haloalkylthio, CrC4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl or CVC4 alkoxycarbonyl; or a phenyl or a 5- or 6-membered heteroaromatic

ring, each ring optionally substituted with CrC4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, CrC4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, N02, CrC4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio, CrC4 alkylsulfmyl, CrC4 alkylsulfonyl, CrC4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C3-C6 (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl or C3-C6 trialkylsilyl. 30. The compound as claimed in 29 wherein J is selected from the group consisting of pyridine, pyrimidine, pyrazole, imidazole, triazole, thiophene, thiazole and oxazole, furan, isothiazole and isoxazole, each optionally substituted with 1 to 3 R'. 3 I. The compound as claimed in 30 wherein .1 is selected from the group consisting of pyridine, pyrimidine, pyrazole, thiophene
and thiazole. each optionally substituted with 1 to 3 R7; R1 and R2 are both H;
R3 is C|-C4 alkyl optionally substituted with halogen, CN, OCH3, or S(0)pCH3; . each R4 is independently H, CH3, CF3, OCF3, OCHF2, S(0)pCF3, S(0)pCHF2, CN or halogen; each R7 is independently H, halogen, CH3, CF3. OCHF2, S(0)pCF3, S(0)pCHF2, OCH2CF3, OCF2CHF2, S(0)pCH2CF3, S(0)pCF2CHF2; or phenyl, pyrazole, imidazole, triazole, pyridine or pyrimidine. each ring optionally substituted with C,-C4 alkyl, C,-C4 haloalkyl, C,-C4 alkoxy, CrC4 haloalkoxy, CrC4 alkylthio. CrC4 alkylsulfmyl, Ct-C4 alkylsulfonyl, halogen orCN; and p is 0, 1 or 2.
32. The compound as claimed in 31 wherein J is a pyridine optionally substituted with 1 to 3 R7.
33. The compound as claimed in 32 wherein one R7 is a phenyl optionally substituted with C|-C4 alkyl, CpC4 haloalkyl, halogen orCN.
34 The compound as claimed in 32 wherein one R7 is a pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted with Cj-C4 alkyl. C|-C4 haloalkyl, halogen or CN.
35. The compound as claimed in 31 wherein J is a pyrimidine optionally substituted with 1 to 3 R7,
36. The compound as claimed in 35 wherein one R7 is a phenyl optionally substituted with Cj-C4 alkyl, CpC4 haloalkyl, halogen or CN.

37. The compound as claimed in 35 wherein one R7 is a r\zole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted with Ci-C4 alkyl, CrC4 haloalkyl, halogen or CN.
38. The compound as claimed in 31 wherein J is a pyrazole optionally substituted with 1 to 3 R7.
39. The compound as claimed in 38 wherein one R7 is a phenyl optionally substituted with Ci-C4 alkyl, C1-C4 haloalkyl, halogen or CN.
40. The compound as claimed in 38 wherein one R7 is a pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted with CpCj alkyl, C|-C4 haloalkyl, halogen or CN.
41. The compound as claimed in 40 wherein wherein R7 is a pyridine optionally substituted with C1-C4 alkyl, C|-C4 haloalkyl, halogen or CN.
42. The compound as claimed in 2Zselected from the group consisting of:
3-methyl-A'-(l-methylethyI)-2-[[4-(trifluoromethyl)benzoyl]amino]-benzamide,
2-mcthyl-A'-[2-methyl-6-[[(l-methylethyl)amino]carbonyl]phenyl]-4-
(trifluoromethyl)benzamide-,
2-methyl-A'-[2-methyl-6-[[(l-methylethyl)amino]carbonyl]phenyl]-6-(trifluoromethyI)-3-pyridinecarboxamide,
l-ethyl-A/-[2-methyl-6-[[(l-methylethyl)amino]carbonyl]phenyl]-3-(trifluoromethyl)-l//-pyrazole-5-carboxamide,
1 -(2-tluorophenyl)-A/-[2-methyl-6-[[( 1 -methylethyl)arnino)carbonyl]phenyl]-3-
(trilluoromethyl)-l//-pyrazole-5-carboxaniide,
1 -(.Vchloro-2-pyridinyl)-Aq2-methyl-6-[[(1 -
methylethyl)amino]carbonyl]phenyl]3-(trifluoromethyl)-l//-pyrazole-5-
carboxamide.
A'-f 2-chloro-6-[[( 1 -methylethy!)amino]carbonyl]phenyl]-1 -(3-chloro-2-
pyridinyl)-3-(tritluoromethyl)-l//-pyrazole-5-carboxamide,
J-bromo-1 -(2-chlorophenyl)-A/-[2-methyl-6-[[( 1 -
methylethyl)amino]carbonyl]phenyl]-l/y-pyrazole-5-carboxamide. and
3-bromo-A'-[2-chloro-6-[[( 1 -methylethyl)amino]carbonyl]phenyl]-1 -(2-
chlorophenyU-1//-pyrazole-S-carboxamide.
43. An arthropodicidal composition comprising an effective amount of a compound of formula 1.

Dated this 27th day of August 2002
Archana Shanker
Of Anand and Anand, Advocates
Attorneys for the applicant

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in-pct-2002-01167-mum-assignment(17-07-2002).pdf

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in-pct-2002-01167-mum-claims(granted)-(02-02-2006).doc

in-pct-2002-01167-mum-claims(granted)-(02-02-2006).pdf

in-pct-2002-01167-mum-correspondence 1(02-02-2006).pdf

in-pct-2002-01167-mum-correspondence 2(14-07-2005).pdf

in-pct-2002-01167-mum-correspondence(ipo)-(13-02-2007).pdf

in-pct-2002-01167-mum-form 1(24-01-2006).pdf

in-pct-2002-01167-mum-form 13(13-04-2005).pdf

in-pct-2002-01167-mum-form 13(30-12-2003).pdf

in-pct-2002-01167-mum-form 19(20-04-2004).pdf

in-pct-2002-01167-mum-form 1a(24-01-2006).pdf

in-pct-2002-01167-mum-form 2(granted)-(02-02-2006).doc

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in-pct-2002-01167-mum-form 3(27-08-2002).pdf

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Patent Number

204978

Indian Patent Application Number

IN/PCT/2002/01167/MUM

PG Journal Number

25/2007

Publication Date

22-Jun-2007

Grant Date

13-Mar-2007

Date of Filing

27-Aug-2002

Name of Patentee

E.I. DU PONT DE NEMOURS AND COMPANY

Applicant Address

1007 MARKET STREET, WILMINGTON, DELAWARE 19898, U.S.A.

Inventors:

#	Inventor's Name	Inventor's Address
1	GEORGE PHILIP LAHM	148, FAIRHILL DRIVE, WILMINGTON, DE 19808, U.S.A.
2	THOMAS MARTIN STEVENSON	103, IROQUOIS COURT, NEWARK, DE 19702, U.S.A.
3	THOMAS PAUL SELBY	116 HUNTER COURT, WILMINGTON, DE 19808, U.S.A.
4	BRIAN J. MYERS	102 EAST RUDDY DUCK CIRCLE, OXFORD, PENNSYLVANIA 19363, U.S.A.

PCT International Classification Number

C07C 235/00

PCT International Application Number

PCT/US01/09338

PCT International Filing date

2001-03-20

PCT Conventions:

#	PCT Application Number	Date of Convention	Priority Country
1	60 / 191,242	2000-03-22	U.S.A.
2	60/254,635	2000-12-11	U.S.A.
3	60/220,232	2000-07-27	U.S.A.
4	60/262,015	2001-01-17	U.S.A.