Title of Invention

"HERBICIDAL PYRIMIDINES"

Abstract

Compounds of Formula I, and their N/-oxides and agriculturally suitable salts, are disclosed which are useful for controlling undesired vegetation wherein R1 is cyclopropyl optionally substituted with 1-5 R5, isopropyl optionally substituted with 1-5 R6, or phenyl optionally substituted with 1-3 R'; R2 is ((O)jC(RlJ)(RIS))kR; R is COjH or a herbicidally effective derivative of CO2H; R3 is halogen, cyano. nitro. OR30. SRZ1 or N(R22)Ra; R* is -N(R24)R25 or -N02; j is 0 or 1; and k is 0 or 1; provided that when k is 0, then j is 0; and R5, R6, R1, R15, R16, R20, R21, R22. R", R24 and R25 are as defined in the disclosure. Also disclosed are compositions comprising the compounds of Formula 1 and a method for controlling undesired vegetation which involves contacting the vegetation or its environment with an effective amount of a'compound of Formula L Also disclosed are compositions comprising a compound of Formula I and at least one additional active ingredient selected front the group consisting of an other herbicide and a herbicide safener.

Full Text

HERBICIDAL PYRIMIDINES FIELD OF THE INVENTION This invention relates to certain pyrimidines, their JV-oxides, agriculturally suitable salts and compositions, and methods of their use for controlling undesirable vegetation. BACKGROUND OF THE INVENTION The control of undesired vegetation is extremely important in achieving high crop efficiency. Achievement of selective control of the growth of weeds especially in such useful crops as rice, soybean, sugar beet, corn (maize), potato, wheat, barley, tomato and plantation crops, among others, is very desirable. Unchecked weed growth in such useful crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. The control of undesired vegetation in noncrop areas is also important. Many products are commercially available for these purposes, but the need continues for new compounds which are more effective, less costly, Jess toxic, environmentally safer of'have different modes of action. World Patent Application Publication WO 92/05159-A discloses pyrimidines useful as plant protectants, especially fungicides. European Patent Application Publication EP-136976-A2 discloses pyrimidines as plant growth regulators. U.S. Patent 5,324,710 discloses sulfonated heterocyclic carboxamide derivatives of pyrimidines as herbicides and growth regulators. SUMMARY OF THE INVENTION This invention is directed to a compound of Formula I including all geometric and stereoisomers, N-oxides or agriculturally suitable salts thereof, agricultural compositions containing them and their use as herbicides: (Figure Removed) wherein R1 is cyclopropyl optionally substituted with 1-5 R5, isopropyl optionally substituted with 1-5 R6, or phenyl optionally substituted with 1-3 R7; R2is((0)jC(Rl5)(Rl6J)kR; R is C02H or a herbicidally effective derivative of CO2H; R3 is halogen, cyano, ratio, OR20, SR21 or N(R22)R23; R4is-N(R24JR25or-N02; each R5 and R6 is independently halogen, C1~C6 alkyl, C1-C6 haloalkyl, alkenyl, C2-C6 haloalkenyl, C1-C3 alkoxy, C1-C2 haloalkoxy, C1-C3 alkylthio or C1-C2 haloalkyltnio; each R7 is independently halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C1-C4 hydroxyalkyl, C2-C4 alkoxyalkyl, C2-C4 haloalkoxyalkyl, C2-C4 alkenyl, C2~C4 haloalkenyl, C3-C4 alkynyl, C3-C4 haloalkynyl, hydroxy, C1-C4 alkoxy, C1:-C4 haloalkoxy, C2-C4 alkenyloxy, C2-C4 haloalkenyloxy, C3-C4 alkynyloxy, C3-C4 haloalkynyloxy, C1-C4 alkylthio, C2C4 haloalkylthio, C1-C4 alkylsulfinyl, C1C4 haloalkylsulfmyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylsulfonyl, C2-C4 alkenylthio, C2C4 haloalkenylthio, C2-C4 alkenylsulfinyl, -04 haloalkenylsulfinyl, C2-C4 alkenylsulfonyl, C2 C 4 haloalkenylsulfonyl, C3-C4 alkynylthio, C3-C4 haloalkynylthio, C3-C4 alkynylsulfinyl, C3-C4 haloalkynylsulfinyl, C3-C4 alkynylsulfonyl, C3-C4 haloalkynylsulfonyl, Cj-C4 alkylamino, C2-Cg dialkylamino, C3-C6 cycloalkylamino, C4-Cg (alkyl)cycloalkylamino, C2-C6 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl,-C3-C6 trialkylsilyl, phenyl, phenoxy and 5- or 6-membered heteroaromatic;rings, each phenyl, phenoxy and 5- or 6-membered heteroaromatic ring optionally substituted with one to three substituents independently selected from R45; or two adjacent R7 are taken together as -OCH2O-, -CH2CH20-, -OCH(CH3)O-, -OC(CH3)20-, -OCF2O-, -CF2CF2O-, -OCF2CF2O- or -CH=CH-CH=CH-; R15 is H, halogen, Cj-C4 alkyl, C\-Ct haloalkyl, hydroxy, Cj-C4 alkoxy or C2-C4 alkylcarbonyloxy; R16 is H, halogen, Cj-C4 alkyl or C!-C4 haloalkyl; or R15 and R16 are taken together as an oxygen atom to form, with the carbon atom to which they are attached, a carbonyl moiety; R20 is H, C-C4 alkyl or C-Cs haloalkyl; R21 is H, C!-C4 alkyl or C haloalkyl; R22 and R23 are independently H or Cj-^ alkyl; R24 is H, C-C4 alkyl optionally substituted with 1-2 R30, C2-C4 alkenyl optionally substituted with 1-2 R31, or C2-C4 alkynyl optionally substituted with 1-2 R32; or R24 is C(=0)R33, nitro, OR34, S(O)2R35, N(R36)R37 or N=C(R62)R63; R25 is H, Cj-^ alkyl optionally substituted with 1-2 R30 or C(=0)R33; or R24 and R25 are taken together as a radical selected from -(CH2)4-, -(CH-, -CH2CH=CHCH2- and-tCHCXCH-, each radical optionally substituted with 1-2 R38; or R24 and R25 are taken together as =C(R39)N(R40)R4l or =C(R42)OR43; each R30, R31 and R32 is independently halogen, Ci-C3 alkoxy, (^-€3 haloalkoxy, C-C3 alkylthio, C-C haloalkylthio, amino, C!-C3 alkylamino, C^-C^ dialkylamino or €2-04 alkoxycarbonyl; each R33 is independently H, Cj-C^ alkyl, Ci-C3 haloalkyl, Cj-C4 alkoxy, phenyl, phenoxy or benzyloxy; R34 is H, Ci-C4 alkyl, Ci-C3 haloalkyl or CHR66c(O)OR67; R35 is Ci-C4 alkyl or C!-C3 haloalkyl; R3« is H, C!-C4 alkyl or C(=O)R«; R37isHorCj-C4alkyl; each R38 is independently halogen, 0^3 alkyl, C-Cs alkoxy, CC3 haloalkoxy, C-C3 alkylthio, C-C3 haloalkylthio, amino, C-C3 alkylamino, dialkylamino or €2-04 alkoxycarbonyl; R40 and R41 are independently H or Ci~C4 alkyl; or R40 and R41 are taken together as -(CH2)4-, -(CH2)5-, -CH2CH=CHCH2- or • • -(CH2)20(CH2)2-; •.R43 is C!-C4 alkyl; • . ;. each R45 is independently halogen, cyano, nitro, Ci~C4 alkyl, C^-C^ haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C2-C4 alkenyl, C2~C4 haloalkenyl, C3-C4 alkynyl, C3-C4 haloalkynyl, €-€4 alkoxy, C-C4 haloalkoxy, Ci-C4 alkylthio, Ci-C4 haloalkylthio, CJ-C4 alkylsulfinyl, Ci~C4 alkylsulfonyl, alkylamino, C-Cg dialkylamino, C3-Cg cycloalkylamino, €4-05 (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-Cg alkoxycarbonyl, alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl or C3-Cg trialkylsilyl; R62 is H, Ci~C4 alkyl or phenyl optionally substituted with 1-3 R65; R63 is H or C!-C4 alkyl; or R62 and R63 are taken together as -(CH2)4- or -(CH2)5-; R64 is H, Cj-Ci4 alkyl, Cj-^ haloalkyl, C!-C4 alkoxy, phenyl, phenoxy or benzyloxy; each R65 is independently CH3, Cl or OCH3; R66 is H, C]i-C4 alkyl or CrC4 alkoxy; R67 is H, C1-C4 alkyl or benzyl; j is Oor 1; and k isO or 1; provided that: (a) when k is 0, then j is 0; (b) when R2 is CH2ORa wherein Ra is H, optionally substituted alkyl or benzyl, then R3 is other than cyano; (c) when R1 is phenyl substituted by Cl in each of the meta positions, the phenyl is also substituted by R7 in the para position; (d) when R1 is phenyl substituted by R7 in the para position, said R7 is other than terf-butyl, cyano or optionally substituted phenyl; (e) when R1 is cyclopropyl or isopropyl optionally substituted with 1-5 R6, then R is other than C(=W)N(Rb)S(O)2-Rc-Rd wherein W is O, S, NRe or NORe; Rb is hydrogen, C1-C4 alkyl, C2 -C6 alkenyl or C2-C6 alkynyl; Rc is a direct bond or CHRf, 0, NRe or NORe; Rd is an optionally substituted heterocyclic or carbocyclic aromatic radical having 5 to 6 ring atoms, the radical being optionally condensed with an aromatic or nonaromatic 5- or' 6-membered ring; each Re is independently H, C1-C3 alkyl, C1-C3 haloalkyl or phenyl; and Rf is H, C1-C3 alkyl or phenyl; and (f) the compound of Formula I is other than diethyl 6-amino-5-nitro-2-phenyl- 4-pyrimidinemalonate. More particularly, this invention pertains to a compound of Formula I, including all • geometric and stereoisomers, N-xides or agriculturally suitable salts thereof. This invention also relates to a.herbicidal composition comprising a herbicidally effective amount of a; compound of Formula I and at least one of a surfactant, a solid diluent or a liquid diluent. This invention further relates to a method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with a herbicidally effective amount of a compound of Formula I (e.g., as a composition described herein). This invention also relates to a herbicidal mixture comprising a herbicidally effective amount of a compound of Formula I and an effective amount of at least one additional active ingredient selected from the group consisting of an other herbicide and a herbicide safener. This invention further relates to a herbicidal composition comprising a herbicidally effective amount of a compound of Formula I, an effective amount of at least one additional active ingredient selected from the group consisting of an other herbicide and a herbicide safener, and at least one of a surfactant, a solid diluent or a liquid diluent. DETAILS OF THE INVENTION As used herein, the terms "comprises," "comprising," "includes," "including," "has," "having" or any other variation thereof, are intended to cover a non-exclusive inclusion. For example, a composition, process, method, article, or apparatus that comprises a list of elements is not necessarily .limited to only those elements but may include other elements not expressly listed or inherent to such composition, process, method, article, or apparatus. Further, unless expressly stated to the contrary, "or" refers to an inclusive or and not to an exclusive or. For example, a condition A or B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present). Also, the indefinite articles "a" and "an" preceding an element or component of the invention are intended to be rtontestrictive regarding the number of instances (i.e. occurrences) of the element or component Therefore "a" or "an" should be read to include one or at least one, and the singular word form of the element or component also includes the plural unless the number is obviously meant to be singular. 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, n-propyl, i-propyl, or the different butyl, pentyl or hexyl isomers. "Alkenyl" includes -straight-chain or branched alkenes such as ethenyl, 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 ethynyl, 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers. "Alkynyl" can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl. "Alkoxy" includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butbxy, pentoxy and hexyloxy isomers.'•'."Alkoxyalkyl" denotes, alkoxy substitution on alkyl. Examples of "alkoxyalkyl" "include CH3OCH2; • :CH3OCH2CH2.. CH3CH2OCH2 and CH3CH2OCH2CH2; : "Alkenyloxy" .includes* straight-chain or branched alkenyloxy moieties. Examples of "alkenyloxy" include H2C=CHCH2O, (CH3)CH=CHCH20 and CH2=CHCH2CH20. "Alkynyloxy" includes straight-chain or branched alkynyloxy moieties. Examples of "alkynyloxy" include HOCH20 and CH3OCCH20. "Alkylthio" includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio and butylthio isomers. "Alkylsulfinyl" includes both enantiomers of an alkylsulfinyl group. Examples of "alkylsuffinyl" include CH3S(0), CH3CH2S(0), CH3CH2CH2S(0), (CH3)2CHS(O) and the different butylsulfinyl isomers. Examples of "alkylsulfonyl" include CH3S(O)2, CH3CH2S(0)2, CH3CH2CH2S(O)2, (CH3)2CHS(0)2 and the different butylsulfonyl isomers. "Alkylamino", "dialkylamino", "alkenylthio", "alkenylsulfinyl", "alkenylsulfonyl", "alkynylthio", "alkynylsulfinyl", "alkynylsulfonyl", and the like, are defined analogously to the above examples. "Cycloalkyl" includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. Examples of "cycloalkylalkyl" include cyclopropylmethyl, cyclopentylethyl, and other cycloalkyl moieties bonded to straight-chain or branched alkyl groups. "Alkylcycloalkyl" denotes alkyl substitution on a cycloalkyl moiety. Examples include 4-methylcyclohexyl and 3-ethylcyclopentyl. The term "heteroarornatic ring" includes fully aromatic heterocycles. Aromatic indicates that each of the ring atoms is essentially in the same plane and has a p-orbital perpendicular to the ring plane, and in which (4n + 2) n electrons, when n is 0 or a positive integer, are associated with the ring to comply with Huckel's rule. The term carbocyclic aromatic radical is synonymous with the term isocyclic aromatic radical. A wide variety of synthetic methods are known in the art to enable preparation of aromatic heterocyclic rings; for extensive reviews see the eight volume set of Comprehensive Heterocyclic Chemistry, A. R. Katritzky and C. W. Rees editors-in-chief, Pergamon Press, Oxford, 1984 and the twelve volume set of Comprehensive Heterocyclic Chemistry II, A. R. Katritzky, C. W. Rees and E. F. V. Scriven editors-in-chief, Pergamon Press, Oxford, 1996. The 5- and 6-membered heteroaromatic rings described for R7 typically comprise 1 to 4 heteroatom ring members, the heteroatom members selected from 0-4 N, 0-1 O and 0-1 S atoms. Exhibit 1 shows examples of heteroaromatic rings; H-l through H-55 are to be construed as illustrative rather than limiting of the heteroaromatic rings within the scope of the present invention. Exhibit 1 (Table Removed) wherein each R71 is independently R45; R71a R72 and R73 are independently H or R45; p is an integer from 0 to 3; and q is an integer from 0 to 2. References herein to R7 groups H-l through H-55 refer to those shown in Exhibit 1. One skilled in the art will appreciate that not all nitrogen-containing heterocycles can form N-oxides since the nitrogen requires an available lone pair of electrons for oxidation to the oxide; one skilled in the art will recognize those nitrogen containing heterocycles which can form N-oxides. One skilled in the art will also recognize that tertiary amines can form W-oxides. Synthetic methods for the preparation of W-oxides of heterocycles and tertiary amines are very well known by one skilled in the art including the oxidation of heterocycles and tertiary amines with peroxy acids such as peracetic and m-chloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperqxides such as t-butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethydioxirane. These methods for the preparation of N-oxides have been extensively described and reviewed in the literature, see for example: T. L. Gilchrist in Comprehensive Organic Syntliesis, vol. 7, pp 748-750, S. V. Ley, Ed., Pergamon Press; M. Tisler and B. Stanovnik in Comprehensive Heterocydic Chemistry, vol. 3, pp 18-20, A.J. Boulton and A. McKillop, Eds., Pergamon Press; M.R. Grimmett and B. R. T. Keene in Advances in Heterocydic Chemistry, vol. 43, pp 149-161, A. R. Katritzky, Ed., Academic Press; M. Tisler and B. Stanovnik in Advances in Heterocydic 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. Werstiuk in Advances in Heterocydic Chemistry, vol. 22, pp 390-392, A. R. Katritzky and A. J. Boulton, Eds., Academic Press. The term "halogen", either alone or hi compound words such as "haloalkyl", includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as "haloalkyl", said alkyl may be partially or fully substituted with halogen atoms which may be the same or different Examples of "haloalkyl" include F3C, C1CH2, CF3CH2 and CF3CC12. The terms "haloalkenyl", "haloalkynyl", "haloalkoxy", "haloalkylthio", and the like, are defined analogously to the term "haloalkyl". Examples of "haloalkenyl" include (C1)2C=CHCH2 and CF3CH2CH=CHCH2. Examples of "haloalkynyl" include HOCCHC1, C F 3 C = C , CC13C=C and FCH2C=CCH2. Examples of "haloalkoxy" include CF3O, CC13CH2O, HCF2CH2CH20 and CF3CH20. Examples of "haloalkylthio" include CC13S, CF3S, CCI3CH2S and C1CH2CH2CH2S. Examples of "haloalkylsulfinyl" include CF3S(O), CC13S(O), CF3CH2S(O) and CF3CF2S(0). Examples of "haloalkylsulfonyl" include CF3S(O)2, CC13S(0)2, CF3CH2S(0)2 and CF3CF2S(0)2. The total number of carbon atoms in a substituent group is indicated by the "Cj-Cj" prefix where i and j are numbers from 1 to 14. For example, C1-C3 alkylsulfonyl designates 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. Examples of "alkylcarbonyl" include C(0)CH3, C(O)CH2CH2CH3 and C(O)CH(CH3)2. Examples of "alkoxycarbonyl" include CH3OC(=O), CH3CH2OC(=0), CH3CH2CH2OC(=0), (CH3)2CHOC(=O) and the different butoxy- or pentoxycarbonyl isomers. In the above recitations, when a compound of Formula I is comprised of one or more heterocyclic rings, all substituents are attached to these rings through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen. When a compound is substituted with a substituent bearing a subscript (e.g., (Rd)1_3) that indicates the number of instances (i.e. occurrences) of said substituent can vary or the substituent is preceded with a numeric range (e.g., 1-3 Rd) indicating the number of instances of said subsituent can vary, then when the number of said instances is greater than 10 1, each instance is independently selected from the group of radicals defined for the substituent Further, when the subscript indicates a range, e.g., (Rd)i_j, then the number of substituent instances may be selected from the integers between i and j inclusive. "-CHtC(0)0(CH2)mrmeans \n ; "-CHfCXCHoU"means When a group contains a substituent which can be hydrogen, for example R15 or R34, then, when this substituent is taken as hydrogen, it is recognized that this is equivalent to said group being unsubstituted. 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 separate, enrich, and/or to selectively prepare said stereoisomers. Accordingly, the present invention comprises compounds selected from Formula I, N-oxides and agriculturally suitable salts thereof. The compounds of the invention may be present as a mixture of stereoisomers, individual stereoisomers, or as an optically active form. The compounds of Formula I wherein R is CC2H (i.e. a carboxylic acid function) are believed to be the compounds that bind to an active site on a plant enzyme or receptor causing herbicidal effect on the plant. Othet compounds of Formula I wherein the substituent R is a group that can be transformed within.plants or the environment to a carboxylic acid function (i.e. CO2H) provide similar herbicidal effects and are within the scope of the present invention. Therefore "a herbicidally effective derivative of CO2H" when used to describe the substituent R in Formula I is defined as any salt, ester, carboxamide, acyl hydrazide, imidate, thioimidate, amidine, acyl halide, acyl cyanide, acid anhydride, ether, acetal, orthoester, carboxaldehyde, oxime, hydrazone, thioacid, thioester, dithiolester, nitrile or any other carboxylic acid derivative known in the art which does not extinguish the herbicidal activity of the compound of Formula I and is or can be hydrolyzed, oxidized, reduced or otherwise metabolized in plants or soil to provide the carboxylic acid function, which depending upon pH, is in the dissociated or the undissociated form. Agriculturally suitable salts of the compounds of the invention are salts formed by contact with acids or bases or through ion exchange such that the derived salts retain •sufficient water solubility for bioavailability and thus herbicidal efficacy and that the counterfoils of the salts are suitable for use in agriculture. The agriculturally suitable 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, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric • acids. The agriculturally suitable salts of the compounds of the invention also include those formed with strong bases (e.g., hydroxides of sodium, potassium, lithium or quaternary ammonium) or amines. One skilled in the art recognizes that because in the environment and under physiological conditions salts of the compounds of the invention are in 5 equilibrium with their corresponding nonsalt forms, agriculturally suitable salts share the biological utility of the nonsalt forms. Particularly useful are agriculturally suitable salts of compounds of Formula I wherein R is C02H (including wherein R2 is C02H) formed with strong bases or amines. As is well known in the art, contact of a carboxylic acid group (C02H) with a base causes 10 deprotonation to give the corresponding carboxylate ion (CO2 e) and a typically positively charged counterion derived from the base. An extensive range of counterions form agriculturally suitable salts of compounds of Formula I wherein R is CO2H, as most of the derived salts have sufficient water solubility for bioavailability. Illustrative and of particular note are salts of compounds of Formula I in which R is CO2H wherein the counterion ion is 15 an alkali metal cation such as lithium, sodium or potassium, quarternary ammonium such as tetramethylammonium, ternary sulfonium such as trimethylsulfonium, or derived from an amine such as dimethylamine, diethanolamine (diolamine), triethanolamine (trolamine). Also particularly useful are ester and thioester derivatives of CO2H as R in the compounds of Formula I. As is well known in the art, ester groups (i.e. C02RAL) result 20 from condensation of a carboxylic acid function (C02H) with an alcohol (i.e. RALOH) wherein RAL is the radical derived from the alcohol; a wide range of methods are known to prepare such esters. Analogously, thioester groups of formula C(0)SRAL may be conceptually viewed as the condensation product of a carboxylic acid function with a thioalcohol (often called a mercaptan) of formula RALSH; a variety of methods are known to 25 prepare such tbioesters. As compounds of Formula I wherein R is C02H are herbicidally active and their derived esters and thioesters are susceptible to hydrolysis (to R being CO2H) particularly in the presence of hydrolytic enzymes, the compounds of Formula I wherein R1 is an ester (i.e. CO2RAL) or thioester (i.e. C(0)SRAL) are generally useful as herbicides. Of the herbicidally effective derivatives of C02H, the ester and thioester derivatives, 30 particularly ester derivatives, are among the most conveniently prepared and useful. If the radical R^ has more than one OH or SH function, the radical may then be condensed with more than one pyrimidine ring system of Formula I having C02H as R. As the derived multiply esterified derivatives can be hydrolyzed to the compound of Formula I having C02H as R, said multiply esterified derivatives are among the herbicidally effective 35 derivatives of CO2H. Illustrative and of note are ester and thioester compounds of Formula I in which R being CO2H is esterified with methanol, ethanol, butanol, 2-butoxyethanol, 2-ethylhexanol, isopropanol, 2-methyJpropanol (isobutanol), octanol isomers (isoctanol) and ethanethiol to form methyl, ethyl, butyl, 2-butoxyethyl, 2-ethylhexyl, isopropyl, 2-methypropyl, isoctyl and ethylthio esters, respectively. Of particular note are the methyl and ethyl esters. Embodiments of the present invention include: Embodiment 1 . A compound of Formula I wherein j is 0. Embodiment 2. A compound of Formula I wherein k is 0. Embodiment 3. A compound of Formula I wherein R15 is H. Embodiment 4. A compound of Embodiment 3 wherein R16 is H. Embodiment 5. A compound of Formula I wherein R is C02R12, CH2OR13, CH(OR46)(OR47), CHO, C(=NOR14)H, C(=NNR48R49)H, C(=0)N(Rl8)R19, C(=S)OR50, C(=0)SR5l, C(=S)SR52 or C(=NR53)YR54; Rl2 is H, -CH{C(O)O(CH2)m}, -N=C(R55)R56; or a radical selected from C1-C14 alkyl, C3-C12 cycloalkyl, C4-C12 alkylcycloalkyl, C4-C12 cycloalkylalkyl, C2-C14 alkenyl, C2-C14 alkynyl and phenyl, each radical optionally substituted with 1-3 R27; or R12 is a divalent radical linking the carboxylic ester function CO2R12 of each of two pyrimidine ring systems of Formula I, the divalent radical selected from -CH2-, -(CH2)2-, -(CH2)3- and -CH(CH3)CH2-; R13 is H, C1-C10 alkyl optionally substituted with 1-3 R28, or benzyl; R14 is H.VC1-C4alkyl, C1-C4haloalkyl or benzyl; • ' is H, C1-C4 alkyl, hydroxy, C1-C4 alkoxy or S(0)2R57; each R27 is independently halogen, cyano, hydroxycarbonyl, C2-C4 alkoxycarbonyl, hydroxy, Ci-C4 alkoxy, (^-€4 haloalkoxy, C!-C4 alkylthio, C1-C4 haloalkylthio, amino, Ci~C4 alkylamino, C2-C4 dialkylamino, -CH{O(CH2)n} or phenyl optionally substituted with 1-3 R44; or two R27 are taken together as -OC(0)O- or -OCCCR^XR58))^^; or two R27 are taken together as an oxygen atom to form, with the carbon atom to which they are attached, a carbonyl moiety; each R28 is independently halogen, C]-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 haloalkylthio, amino, C1~C4 alkylamino or C2-C4 dialkylamino; or two R28 are taken together as an oxygen atom to form, with the carbon atom to which they are attached, a carbonyl moiety; each R44 is independently halogen, C1-C4 alkyl, C1 -C3haloalkyl, hydroxy, C1 -C4alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, C1-C3 haloalkylthio, amino, C1~C3 alkylamino,C2-C4 dialkylamino or nitro; R46 and R47 are independently C1-04 alkyl or C1~C3, haloalkyl; or R46 and R47 are taken together as -CH2CH2-, -CH2CH(CH3)- or -(CH2)3-; R48 is H, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkylcarbonyl, C2-C4 alkoxycarbonyl or benzyl; R49 is H, C1-C4 alkyl or C1-C4 haloalkyl; R50, R51 and R52 are H; or a radical selected from C1-C14 alkyl, C3-C12 cycloalkyl, C4-Cl2 alkylcycloalkyl, C4-C12 cycloaikylalkyl, C2-C4 alkenyl and C2-C]4 alkynyl, each radical optionally substituted with 1-3 R27; YisO, SorNR61; R53 is H, C1-C3 alkyl. C1~C3 haloalkyl, C2-C4 alkoxyalkyl, OH or C1-C3 alkoxy; R54 is C1-C3 alkyl, C1-C3 haloalkyl or C2-C4 alkoxyalkyl; or R53 and R54 are taken together as -(CH2)2-, -CH2CH(CH3)- or -(CH2)3-; R55 and R56 are independently C1-C4 alkyl; R57 is C1-C4 alkyl, C1-C3 haloalkyl or NR59R60; each R58 is independently selected from H and C1-C4 alkyl; R59 and R60 are independently H or C1-C4 alkyl; R61 is H, C1-C3 alkyl, C1-C3 haloalkyl or C2-C4 alkoxyalkyl; m is an integer from 2 to 3; and n is an integer from 1 to 4. Embodiment 6. A compound of Formula I wherein when R1 is optionally substituted cyclopropyl, then R2 is other than alkoxyalkyl or alkylthioalkyl. Embodiment 7. A compound of Formula I wherein R2 is other than alkoxyalkyl or alkylthioalkyl. Embodiment 8. A compound of Embodiment 5 wherein R2 is CO2R12, CH2OR13, CH(OR46)(OR47), CHO, C(=NOR14)H, C(=NNR48R49)H, (0)jC(R15)(R16)C02R17, C(=0)N(R18)R19, C(=S)OR50, C(=O)SR51, C(=S)SR52 or C(=NR53)YR54; R17 is C1-C10 alky] optionally substituted with 1-3 R29, or benzyl; and each R29 is independently halogen, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 haloalkylthio, amino, C1-C4 alkylamino or C2-C4 dialkylamino. Embodiment 9. A compound of Embodiment 8 wherein when R2 is CH2OR13, then R13 is other than alkyl. Embodiment 10. A compound of Embodiment 8 wherein when R2 is CH2OR13 ; then R13 is other than optionally substituted alkyl. Embodiment 11. A compound of Embodiment 8 wherein R2 is other than CH2OR13. Embodiment 12. A compound of Embodiment 8 wherein j is 0. AMENDED SHEET Embodiment 13. A compound of Embodiment 12 wherein R2 is CO2R12, CH2OR13, CHOorCH2CO2R17. Embodiment 14. A compound of Embodiment 13 wherein R2 is CO2R12. Embodiment 15. A compound of Embodiment 14 wherein R12 is H, C1C8 alkyl or C1 alkyl substituted with phenyl optionally substituted with 1-3 R44. Embodiment 16. A compound of Embodiment 15 wherein R12 is H, C1-C4 alkyl or C1 alkyl substituted with phenyl optionally substituted with 1-3 R44. Embodiment 17. A compound of Embodiment 16 wherein R12 is H, C1-C4 alkyl or benzyl. Embodiment 18. A compound of Formula I wherein R2 is CO2H, an agriculturally suitable salt or an ester or thioester derivative thereof. Embodiment 19. A compound of Embodiment 18 wherein R2 is CO2H, an agriculturally suitable salt or an ester derivative thereof. Embodiment 20. A compound of Formula I wherein R1 is cyclopropyl optionally substituted with 1-5 R5. Embodiment 21. A compound of Fonnula I wherein R1 is isopropyl optionally substituted with 1-5 R6. Embodiment 22. A compound of Formula I wherein R1 is phenyl optionally substituted with 1-3 R7. Embodiment 23. A compound of Formula I wherein R1 is cyclopropyl optionally substituted with 1-5 R5 or isopropyl optionally substituted with 1-5 R6. Embodiment 24. A compound of Formula I wherein R1' is cyclopropyl optionally substituted with 1-5 R5 or phenyl optionally substituted with 1-3 R7. Embodiment 25. A compound of Formula I wherein R1 is isopropyl optionally substituted with 1-5 R6 or phenyl optionally substituted with 1-3 R7. Embodiment 26. A compound of Formula I wherein R1 is other than cyclopropyl. Embodiment 27. A compound of Formula I wherein R1 is cyclopropyl optionally substituted with 1-2 R6 or phenyl optionally substituted with 1-3 R7. Embodiment 28. A compound of Embodiment 27 wherein R1 is cyclopropyl optionally substituted with 1-2 R6. Embodiment 29. A compound of Embodiment 27 wherein R1 is cyclopropyl or phenyl optionally substituted with 1-3 R7. Embodiment 30. A compound of Embodiment 28 wherein R1 is cyclopropyl. Embodiment 31. A compound of Embodiment 27 wherein R1 is phenyl optionally substituted with 1-3 R7. Embodiment 32. A compound of Embodiment 27 wherein R1 is cyclopropyl or phenyl substituted with a R7 radical in the para position and optionally with 1-2 R7 in other positions. Embodiment 33. A compound of Embodiment 32 wherein R1 is cyclopropyl or phenyl substituted with a halogen, methyl or methoxy radical in the para position and optionally with 1-2 radicals selected from halogen and methyl in other positions. Embodiment 34. A compound of Embodiment 33 wherein R1 is cyclopropyl or phenyl substituted with a halogen radical in the para position and optionally with 1-2 radicals selected from halogen and methyl in other positions. Embodiment 35. A compound of Embodiment 34 wherein R1 is cyclopropyl or phenyl substituted with a Br or Cl radical in the para position and optionally with 1-2 radicals selected from halogen and methyl in other positions. Embodiment 36. A compound of Embodiment 35 wherein R1 is phenyl substituted with a Br or Cl radical in the para position and optionally with 1-2 radicals selected from halogen and methyl in other positions. Embodiment 37. A compound of Embodiment 35 wherein R1 is cyclopropyl or phenyl substituted with a Br or Cl radical in the para position. Embodiment 38. A compound of Embodiment 37 wherein R* is phenyl substituted with a Br or Cl radical in the para position. Embodiment 39. A compound of Formula I wherein R7 is other than cyano. Embodiment 40. A compound of Formula I wherein R7 selected from other than optionally substituted phenyl, phenoxy and 5- and 6-membered heteroaromatic rings. Embodiment 41. A compound of Formula I wherein each R7 is independently selected from halogen, C1-C2 alky,Cl-C2 haloalkyl, C1-C2 alkoxy or C1~C2 haloalkoxy; or two adjacent R7 are taken together as -OCH^O-, -CI^CH^O-, -OCH(CH3)0-, -OC(CH3)20-, -OCF2O-, -CF2CF20-, -OCF2CF20- or -CH=CH-CH=CH-. Embodiment 42. A compound of Embodiment 41 wherein each R7 is independently selected from halogen, C1~C2 alkyl, C1~C2 haloalkyl, C1-C2 alkoxy or C1~C2 haloalkoxy; or two adjacent R7 are taken together as -OCH2O-, -CH2CH20-, -OCH(CH3)0- or -OCF20-. Embodiment 43. A compound of Embodiment 42 wherein each R7 is independently selected from halogen, C1-C2 alkyl, C1 fluoroalkyl, C1-C2 alkoxy or C1 fluoroalkoxy. Embodiment 44. A compound of Formula I wherein each R7 is independently selected from halogen, methyl and methoxy. Embodiment 45. A compound of Embodiment 44 wherein each R7 is independently selected from halogen and methyl. Embodiment 46. A compound of .Embodiment 45 wherein each R7 is independently selected from F, Cl and Br. Embodiment 47. A compound of Embodiment 46 wherein each R7 is independently selected from Cl and Br. Embodiment 48. A compound of Formula I wherein R3 is other than cyano. Embodiment 49. A compound of Formula I wherein R3 is other than nitro. Embodiment 50. A compound of Formula I wherein R3 is halogen, nitro, OR20, SR21 Embodiment 51. A compound of Embodiment 50 wherein R3 is halogen. Embodiment 52. A compound of Embodiment 51 wherein R3 is Br or Cl. Embodiment 53. A compound of Embodiment 52 wherein R3 is Cl. Embodiment 54. A compound of Formula I wherein R4 is -N(R24)R25. Embodiment 55. A compound of Formula I wherein R24 is other than C2-C4 alkynyl optionally substituted with 1-2 R32. Embodiment 56. A compound of Formula I wherein R24 is H, C(O)R33 or C1-C4 alkyl optionally substituted with R30; R25 is H or C1-C2 alkyl; or R24 and R25 are taken together as C(R39)N(R40)R41. Embodiment 57. A compound of Embodiment 56 wherein R24 is H, C(O)CH3 or C1-C4 alkyl optionally substituted with R30; and R25 is H or C1-C2 alkyl. Embodiment 58. A compound of Embodiment 57 wherein R24 and R25 are independently H or methyl. . Embodiment 59. A compound of Embodiment 58 wherein R24 and R25 are H. Embodiment 60. A compound of Formula I wherein R30 is halogen, methoxy, Cj fluoroalkoxy, methylthio, Cj fluoroalkylthio, amino, methylamino, dimethylamino or methoxycarbonyl. Embodiment 61. A compound of Formula I wherein R33 is H or C1-C3 alkyl. Embodiment 62. A compound of Embodiment 61 wherein R33 is CH3. Embodiment 63. A compound of Formula I wherein R39 is H or C1-C2 alkyl. Embodiment 64. A compound of Formula I wherein R40 and R41 are independently H or C1-C2 alkyl. Embodiment 65. A compound of Formula I wherein R3 is other than OH. Embodiment 66. A compound of Formula I wherein R3 is other than OR20. Embodiment 67. A compound of Formula I wherein when j is 1, and R1 is isopropyl substituted with at least one R6 being halogen, then R24 and R25 are each H. Embodiment 68. A compound of Formula I wherein when j is 1 , R1 is optionally substituted isopropyl, the R24 and R25 are each H. Embodiment 69. A compound of Formula I wherein when j is 1 , then R24 and R25 are each H. Embodiment 70. A compound of Formula I wherein when j is 1, then R6 is other than halogen. Embodiment 71. A compound of Formula I wherein when j is 1, then R1 is other than optionally substituted isopropyl. Embodiment 72. A compound of Formula I wherein when j is 1, then R1 is cyclopropyl optionally substituted with 1-5 R5, isopropyl, or phenyl optionally substituted with 1-3 R7. Embodiment 73. A compound of Formula I wherein when j is 1, then R1 is cyclopropyl, isopropyl, or phenyl optionally substituted with 1-3 R7. Embodiment 74. A compound of Formula I wherein when R1 is phenyl optionally substituted with 1-3 R7 then R is other than cyano. Embodiment 75. A compound of Formula I wherein R is other than cyano. Embodiment 76. A compound of Embodiment 5 wherein when R1 is phenyl optionally substituted with 1-3 R7 then R is CO2R12. Embodiment 77. A compound of Embodiment 5 wherein R is CO2R12. Embodiment 78. A compound of Embodiment 8 wherein when R1 is phenyl optionally substituted with 1-3 R7 then R2 is C02R12. Embodiment 79. A compound of Embodiment 8 wherein R2 is C02R12. Embodiment 80. A compound of Formula I wherein when R1 is phenyl optionally substituted with 1-3 R7 then R24 is H, C(=O)R33, nitre, OR34, S(O)2R35 or N(R36)R37, and R25 is H or C(=0)R33. Embodiment 81. A compound of Formula I wherein when R1 is phenyl optionally substituted with 1-3 R7 then R24 and R25 are each H. Embodiment 82. A compound of Formula I wherein R24 is H, C(=O)R33, nitro, OR34, S(0)2R35 or N(R36)R37, and R25 is H or C(=O)R33. . Embodiment 83. A compound of Formula I wherein R24 and R25 are each H. Embodiment 84. A compound of Formula I wherein when R1 is cyclopropyl or isopropyl optionally substituted with 1-5 R6, then R is other than C(=W1)N(Rbl)S(0)2-Rcd wherein W comprises at least one atom; Rbl comprises at least one atom and Rcd comprises at least one atom. Embodiment 85. A compound of Formula I wherein when R1 is cyclopropyl optionally substituted with 1-5 R5 or isopropyl optionally substituted with 1-5 R6, then R is other than C(=W1)N(Rb1)S(O)2-Rcd wherein W comprises at least one atom; Rbl comprises at least one atom and Rcd comprises at least one atom. Embodiment 86. A compound of Formula I wherein R is other than C(=W1)N(Rbl)S(O)2-Rcd wherein W comprises at least one atom; Rbl comprises at least one atom and R^ comprises at least one atom. Embodiment 87. A compound of Embodiment 5 wherein R18 is H, C1-C4 alkyl, hydroxy or C1-C4 alkoxy. Embodiment 88. A compound of Embodiment 8 wherein R18 is H, C1-C4 alky], hydroxy or C1-C4 alkoxy. Embodiment 89. A compound of Formula I wherein each R5 and R6 is independently halogen, C1~C2 allcy1 or C1-C2 haloalkyl. Embodiment 90. A compound of Formula I wherein R15 is H, halogen, C1-C4 alkyl, C1-C4 haloalkyl, hydroxy, C1-C4 alkoxy or C2-C4 alkylcarbonyloxy. Embodiment 91. A compound of Formula I wherein R16 is H, halogen, C1-C4 alkyl or C1-C4 haloalkyl. Embodiment 92. A compound of Formula I wherein R24 is H, C1-C4 alkyl optionally substituted with 1-2 R30, C2-C4 alkenyl optionally substituted with 1-2 R31, or C2-C4 alkynyl optionally substituted with 1-2 R32; or R24 is C(=O)R33, nitro, OR34, S(O)2R35 or N(R36)R37, Embodiment 93. A compound of Formula I wherein each R33 is independently H, C1-C4 alkyl, C1-C3 haloalkyl, C1-C4 alkoxy, phenoxy or benzyloxy. Embodiment 94. A compound of Formula I wherein R34 is H, C1-C4 alkyl or C1-C3 haloalkyl. Embodiment 95. A compound .of Formula-1 wherein R36 is H or C1-C4 alkyl. Embodiment 96. A compound of Embodiment 5 wherein R12 is H; or a radical selected from C1-C14 alkyl, C3-C12 cycloalkyl, C4-C12 alkylcycloalkyl, C4-C12 cycloalkylalkyl, C (Table Removed) (Hordeum vulgare), and wheat (Triticum aestivum) were planted and treated preemergence with test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant. At the same time, plants selected from these crop and weed species were treated with postemergence applications of some of the test chemicals formulated in the same manner. Plants ranged in height from 2 to 18 cm (1- to 4-leaf stage) for postemergence treatments. Treated plants and controls were maintained in a controlled growth environment for 15 to 25 days after which time all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table D, are based on a scale of 0 to 100 where 0 is no ;effect and 100 is complete control. A dash (-) response means no test result. (Table Removed) TESTE Three plastic pots (ca. 16-cm diameter) per rate were partially filled with sterilized Tama silt loam soil comprising a 35:50:15 ratio of sand, silt and clay and 2.6% organic . matter. Separate plantings for each of the three pots were as follows. Seeds from the U.S. of ducksalad (Heteranthera limosa), smallflower umbrella sedge (Cyperus diffonnis) and purple redstem (Amnannia coccinea), were planted into one 16-cm pot for each rate. Seeds from the U.S. of rice flatsedge (Cyperus iria\ bearded (brdd.) sprangletop (Leptochloa fusca ssf.fascicularis), one stand of 9 or 10 water seeded rice seedlings (Oryza sativa cv. 'Japonica - M202'), and one stand of 6 transplanted rice seedlings (Oryza sativa cv. 'Japonica - M202') were planted into one 16-cm pot for each rate. Seeds from the U.S. of bamyardgrass (Echinochloa crus-galli), late watergrass (Echinochloa oryzicola), early watergrass (Echinochloa oryioides) and junglerice (Echinochloa colona} were planted into one 16-cm pot for each rate. Plantings were sequential so that crop and weed species were at the 2.0 to 2.5-leaf stage at time of treatment. Potted plants were grown in a greenhouse with day/night temperature settings of 29.5/26.7 °C, and supplemental balanced lighting was provided to maintain a 16-hour photoperiod. Test pots were maintained in the greenhouse until test completion. At time of treatment, test pots were flooded to 3 cm above the soil surface, treated by application of test compounds directly to the paddy water, and then maintained at that water depth for the duration of the test. Effects of treatments on rice and weeds were visually evaluated by comparison to untreated controls after 21 days. Plant response ratings, summarized in Table E, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (—)• response means no test result. Table E Compounds Table E Compounds 500 g ai/ha 44 61 62 500 g ai/ha 44 61 62 Flood Flood Barnyardgrass 10 65 100 Rice, Water Seeded 20 35 60 Ducksalad 100 100 100 Sedge, Umbrella 100 100 100 Flatsedge, Rice - 95 100 Sprangletop, Brdd. 95 65 75 Junglerice 20 '25 65 Watergrass, Early 0 25 0 Redstem 75 100 100 Watergrass, Late 20 25 20 Rice, Transplanted 0 25 30 Table E Compounds 250 g ai/ha 37 44 58 61 62 63 64 65 66 67 69 70 71 72 Flood Barnyardgrass 0 0 - 0 50 - - - 35 40 - 0 60 0. Ducksalad 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Flatsedge, Rice 90 - 100 40 65 85 100 100 0 60 100 65 0 100 .Junglerice > 0 20 0 25 50 30 0 40 0 65 0 0 45 o' Redstem : 80 50 95 100 95 75 80 60 100 85 30 0 30 100 Rice, Transplanted 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 Rice, Water Seeded 0 0 20 10 10 30 0 10 0 0 0 0 0 0 Sedge, Umbrella 95 100 100 95 100 80 100 100 0 70 100 60 70 100 I Sprangletop, Brdd. 0 50 60 65 45 65 0 40 0 30 0 0 60 0 Watergrass, Early - 0 - 2 0 0 0 0 1 0 0 0 0 0 0 0 Watergrass, Late 0 0 0 2 0 20 0 2 0 2 5 0 0 0 0 0 0 Table E Compounds 250 g ai/ha 73 74 84 88 91 94 95 96 98 99 111 117 118 128 Flood Barnyardgrass . 100 0 8 5 0 1 0 00 0 0 0 0 0 00 Ducksalad 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Flatsedge, Rice 45 95 80 100 - 100 0 100 100 100 0 100 100 80 Junglerice 0 65 .50 90 70 0 0 0 0 0 0 0 65 10 Redstem 100 25 100 65 50 100 80 100 40 45 75 30 85 90 Rice, Transplanted 0 0 20 0 10 20 15 20 0 '20 0 20 0 0 Rice, Water Seeded 0 0 30 0 20 10 15 10 0 20 0 0 0 0 Sedge, Umbrella 85'100 100 95 100 100 95 100 60 - 75 100 100 100 Sprangletop, Brdd. 70 0 40 95 30 40 0 0 0 0 0 0 85 80 Watergrass, Early 00 3 0 5 0 0 0 0 0 0 0 0 0 0 0 Watergrass, Late 20 0 20 Table E (Table Removed) Watergrass, Late O O O O O O O O O O O O O O Table E Compounds Table E Compounds 125 g ai/ha 129 133 125 g ai/ha 129 133 Flood Flood Barnyardgrass 0 0 Rice, Water Seeded 0 0 Ducksalad 100 100 ' Sedge, Umbrella' 100 100 Flatsedge, Rice 100 95 Sprangletop, Brdd. 0 0 Junglerice 0 0 Watergrass, Early 0 0 Redstem BO 75 Watergrass, Late 0 0 Rice, Transplanted 0 0 Table E Compounds 64 g ai/ha 37 44 58 61 62 63 64 65 66 67 69 70 71 72 Flood Barnyardgrass 0 0 - 0 0 - - - - 0 0 0 0 - Ducksalad 100 100 100 100 100 65 100 100 100 100 100 100 100 100 Flatsedge, Rice 0 - 100 0 0 75 90 100 0 30 100 0 0 100 Junglerice •... 0 0 0 2 0 3 0 0 0 0 0 0 0 0.0. 0 Redstem- •• . 30 10 85 80 85 65 60 30 0 0 0 0 0 25 Rice, Transplanted 0 0 0 0 0 0 0 0 - 0 0 0 0 0 0 Rice, Water Seeded 0 0 0 0 0 - 0 0 0 0 0 0 0 0 0 Sedge, Umbrella 50 90 95 75 80- 75 85 85 .0 0 30 0 0 75 Sprangletop, Brdd. 0 30 60 35 0 40 . 0 0 0 0 0 0 - 0 Watergrass, Early - 0 - 0 0 0 0 0 0 0 0 0 0 0 Watergrass, Late 0 0 0 2 0 2 0 0 0 0 0 0 0 0 0 0 Table E Compounds 64 g ai/ha 73 74 84 88 91 94 95 96 98 99 111 117 118 128 Flood Barnyardgrass 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 Ducksalad 100 100 100 100 100 100 100 100 100 100 85 100 100 100 Flatsedge, Rice 0 0 60 100 - 100 0 100 100 100 0 100 95 0 Junglerice 0 0 0 0 0 0 0 . 0 0 0 0 0 4 5 0 • Redstem 90 0 20 0 0 75 30 90 0 - 30 0 30 80 Rice, Transplanted 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 Rice, Water Seeded 0 0 0 0 1 0 - 0 0 0 0 0 0 0 0 Sedge, Umbrella 0 80 80 - 30 100 95 100 6 0 - 0 100 100 70 Sprangletop, Brdd. 00 0,0 ' 0 0 0 0 0 0 0 0 0 0 Watergrass, Early 00 1 0 0 0 0 0 0 0 0 0 0 0 0 Watergrass, Late Table E (Table Removed) Watergrass, Late 0 0 0 0 0 0 0 0 0 0 0 0 0 TESTF Seeds or nutlets of plant species selected from (turf) bermudagrass (Cynodon dactylon), Kentucky bluegrass (Poa pratensis), bentgrass (Agrostis palustris), hard fescue (Festuca ovind), large crabgrass (Digitaria sanguinalis), goosegrass (Eleusine indica), dallisgrass (Paspalum dilatation), annual bluegrass (Poa annud), common chickweed (Stellaria media), dandelion (Taraxacum officinale), white clover (Trifolium repens), and yellow nutsedge (Cyperus esculentus) were planted and treated preemergence with the test chemical formulated in a non-phytotoxic solvent mixture which included a surfactant. At the same time, plants selected from these crop and weed species were treated with postemergence applications of the test chemical formulated in the same manner. Plants ranged in height from 2 to 18 cm (1- to 4-leaf stage) for postemergence treatments. Treated plants and controls were maintained in a greenhouse for 12 to 14 days, after which time all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table F, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result. Table F Compound (Table Removed) Seeds or nutlets of plant species selected from bermudagrass (Cynodon dactylon), Surinam grass (Brachiaria decumbens), large crabgrass (Digiiana sanguinalis'), green foxtail (Setaria viridis), goosegrass (Eleusine indica), johnsongrass (Sorghum halepense), kochia (Kochia scoparia), pitted momingglory (Ipomoea lacunosa), purple nutsedge (Cyperus rotundus), common ragweed (Ambrosia elatior), black mustard (Brassica nigrd), (Table Removed) guineagrass (Panicum maximum), dallisgrass (Paspalum dilatation), bamyardgrass (Echinochloa crus-galli), southern sandbur (Cenchrus ediinatus), common sowthistle (Sonchus oleraceous), prickly sida (Sida spinosa), Italian ryegrass (Lolium multiflorum), common purslane (Portulaca oleracea), broadleaf signalgrass (Brachiaria platyphylla), common groundsel (Senecio vulgaris), common chickweed (Stellaria media), tropical spidenvort (Commelina benghalensis), annual bluegrass (Poa annua), downy bromegrass (Bromus tectorurri), itchgrass (Rottboellia cochinchinensis), quackgrass (Elytrigia repens), Canada horseweed (Conyza caiiadensis), field bindweed (Convolvulus arvensis), spanishneedles (Bidens bipinnata), common mallow (Malva sylvestris), and Russian thistle (Salsola kali) were planted and treated preemergence with test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant. At the same time, plants selected from these weed 'species were treated with postemergence applications of some of the test chemicals formulated in the same manner. Plants ranged in height from 2 to 18 cm (1- to 4-leaf stage) for postemergence treatments. Treated plants and controls were maintained in a greenhouse for 12 to 21 days, after which time all species were compared to controls and visually evaluated. At a different time, established container-grown' grape (Vitus vinifera) vines, and olive (Olea europaea) and orange (Citrus sinensis) trees were treated with some of the test chemicals formulated in the same manner and applied to the soil surface and the lower 5.cm of the plant vines or trunks (post-directed application). Plants ranged in height from 30 to 100 cm. The applications were made using a hand sprayer delivering a volume of 990 L/ha. Treated plants and controls were maintained in a greenhouse for 28 days, after which time the treated plants were compared to controls and visually evaluated. Also at a different time, seed pieces (nodes) of sugarcane (Saccharum officinarum) were planted and treated preemergence and/or postemergence with some of the test chemicals formulated in the same manner. Treated plants and controls were maintained in a greenhouse for 14 days, after which time the treated plants were compared to controls and visually evaluated. Plant response ratings, summarized in Table G, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result. Table G Compound Table G Compound (Table Removed) TESTH This test evaluated the effect of mixtures of compound 1 with diflufenzopyr on several plant species. Seeds of test plants consisting of large crabgrass (DIGSA, Digitaria sanguinalis (L.) Scop.), lambsquarters (CHEAL, Chenopodium album L.), redroot pigweed (AMARE, Amaranthus retroflexus 'L.), cocklebur (XANST, Xanthium strumarium L.), bamyardgrass (ECHCG; Echinochloa crus-galli (L.) Beauv.), com (ZEAMD, Zea mays L. cv. 'Pioneer 33G26'), scarlet (red) morningglory (IPOCO, Ipomoea cocdnea L.), giant foxtail (SETFA, Setaria faberi Hemn.) and velvefleaf (ABUTH, Abutilon theophrasti Medik.) were planted in pots containing Redi-Earth® planting medium (Scotts Company, 14111 Scottslawn Road, Marysville, Ohio 43041) comprising spaghnum peat moss, venniculite, wetting agent and starter nutrients. Seeds of small-seeded species were planted about 1 cm deep; largetr seeds were planted about 2.5 cm deep. Plants were grown in a greenhouse using supplemental lighting to maintain a photoperiod of about 14 hours; daytime and nighttime temperatures were about 25-30 °C and 22-25 °C, respectively. Balanced fertilizer was applied through the watering system. The plants were grown for 7 to 11 days so that at time of treatment the plants ranged in height from 2 to 18 cm (1- to 4- leaf stage). Treatments consisted of Compound 1 and diflufenzopyr alone and in combination, suspended or dissolved in an aqueous solvent comprising glycerin and Tween nonionic surfactant and applied as a foliage spray using a volume of 541 L/ha. Each treatment was replicated four times. The application solvent was observed to have no effect compared to untreated check plants. Treated plants and controls were maintained in the greenhouse and watered as needed with care to not wet the foliage for the first 24 hours after treatment. The effects on the plants' approximately 3 weeks after treatment were visually compared to untreated controls. Plant response ratings were calculated as the means of the four replicates, based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. Colby's Equation was used to determine the herbicidal effects expected from the mixtures. Colby's Equation (Colby, S. R. "Calculating Synergistic and Antagonistic Responses of Herbicide Combinations," Weeds, 15(1), pp 20-22 (1967)) calculates the expected additive effect of herbicidal mixtures, and for two active ingredients is of the form: wherein Pa+b is the percentage effect of the mixture expected from additive contribution of the individual components, Pa is the observed percentage effect of the first active ingredient at the same use rate as in the mixture, and Pb is the observed percentage effect of the second active ingredient at the same use rate as in the mixture. The results and additive effects expected from Colby's Equation are listed in Table H. Table H - Observed and Expected Results from Compound 1 Alone and in Combination (Table Removed) * Application rates are grams of active ingredient per hectare (g a.i./ha). "Obsd." is observed effect "Exp." is expected effect calculated from Colby's Equation. As can be seen from the results listed in Table H, most of the observed results were greater than expected from the Colby Equation, and in some cases much greater. Most notable was the greater than additive effect observed on crabgrass, barnyardgrass, com and giant foxtail. The increase was less noticeable for other test species, but primarily because the expected effect was already near 100% at the rates tested. TEST I This test evaluated the effect of mixtures of compound 9 with metsulfuron-methyl and with a 5:1 by weight combination of chlorsulfuron and metsulfuron-methyl on several plant species. Seeds of test plants consisting of wheat (TRZAW; Triticum aestivum), wild buckwheat, (POLCO; Polygonum convolvulus), redroot pigweed (AMARE; Amaranthus retroflexus), wild mustard (SINAR; Sinapis arvensis), catchweed bedstraw (GALAP; Galium aparine), Russian thistle (SASKR; Salsola kali), common chickweed (STEME; Stellaria media), kochia (KCHSC; Kochia scoparia), and lambsquarters (CHEAL; Chenopodium album) were planted into a blend of loam soil and sand. Plants were grown in a greenhouse using supplemental lighting to maintain a photoperiod of about 14 hours; daytime and nighttime temperatures were about 23 °C and 16 °C, respectively. Balanced fertilizer was applied through the watering system. The plants were grown for 10 to 23 days so that at time of treatment the plants ranged from 2- to 8-leaf stage. Treatments consisted of Compound 9, metsulfuron-methyl, and chlorsulfuron-metsulfuron-methyl (5:1) alone and in combination. The treatments were formulated in a non-phytotoxic solvent mixture which included a surfactant and applied as a foliage spray using a volume of 28CM58 L/ha. Each treatment was replicated three times. The application solvent was observed to have no effect compared to untreated check plants. Treated plants and controls were maintained in the greenhouse and watered as needed with care to not wet the foliage for the first 24 hours after treatment. The effects on the plants approximately 17 days after treatment were visually compared to untreated controls. Plant response ratings were calculated as the means of the .three replicates, based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. Colby's Equation was used to determine the herbicidal effects expected from the mixtures. The results and additive effects expected from Colby's Equation are listed in Table I. Table I - Observed and Expected Results from Compound 9 Alone and in Combination with Metsulfuron-Methyl and with ChlorsuUuron-Metsulfuron-Methyl (5:1)* Application Rate (g a.i./ha) (Table Removed) * Application rates are grams of active ingredient per hectare (g a.iTha). "Obsd." is observed effect. "Exp." is expected effect calculated from Colby's Equation. As can be seen from the results listed in Table I, some of the observed results for weeds were greater than expected from the Colby Equation. Most notable was the greater than additive effect observed on wild buckwheat, kochia, and lambsquarters. In addition, observed results for nearly all treatments on wheat were less than expected from the Colby Equation, suggesting crop safening. TEST; This test evaluated the effect of mixtures of compound 58 with azimsulfuron on several plant species. Three plastic pots (ca. 16-cm diameter) per rate were partially filled with sterilized Tama silt loam soil comprising a 35:50:15 ratio of sand, silt and clay and 2.6% organic matter. Separate plantings for each of the three pots were as follows. Seeds from the U.S. of ducksalad (HETLI; Heterantiiera limosa), smallflower umbrella sedge (CYPDI; Cyperus difformis) and purple redstem (AMMCO; Ammanma cocanea), were planted into one 16-cm pot for each rate. Seeds from the U.S. of bearded sprangletop (LEFUF; Leptochloa fusca ssp. fascicularis), one stand of 9 or 10 water-seeded rice seedlings (ORYSW; Oryza sativa cv. 'Japonica - M202'), and one stand of 6 transplanted rice seedlings (ORYSP; Oryza sativa cv. 'Japonica - M202') were planted into one 16-cm pot for each rate. Seeds from the U.S. of barnyardgrass (ECHCG; Echinochloa crus-galli), late watergrass (ECOR2; Echinochloa oryzicold), early watergrass (ECHOR; Echinochloa oiyzoides) and junglerice (ECHCO; Echinochloa colond) were planted into one 16-cm pot for each rate. Plantings were sequential so that crop and weed species were at the 2.0 to 2.5- leaf stage at time of treatment. Potted plants were grown in a greenhouse with day/night temperature settings of 29.5/26.7 °C, and supplemental balanced lighting was provided to maintain a 16-hour photoperiod. Test pots were maintained in the greenhouse until test completion. At time of treatment, test pots were flooded to 3 cm above the soil surface and then treated by application directly to the paddy water of test compounds formulated in a nonphytotoxic solvent mixture which included a surfactant. The pots were maintained at the 3-cm water depth for the duration of the test. Treatments consisted of compound 58 and azimsulfuron alone and in combination. ' Effects of treatments on rice and weeds were visually evaluated by comparison to untreated controls after 21 days. Plant response ratings were calculated as the means of the three replicates and are summarized in Table J. The ratings are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result. Colby's Equation was used to determine the herbicidal effects expected from the mixtures. The results and additive effects expected from Colby's Equation are listed in Table J. Table J - Observed and Expected Results from Compound 58 Alone and in Combination with Azimsulfuron* Application Rate (g a.i7ha) (Table Removed) * Application rates are grams of active ingredient per Hectare (ga.L/ha). "Obsd." is observed effect. "Exp." is expected effect calculated from Colby's Equation. Seeds of plant species selected from sulfonylurea herbicide-susceptible (SUsusceptible) and sulfonylurea herbicide-resistant (SU-resistant) catchweed bedstraw (GALAP; Galium aparine) and wheat (TRZAW; Triticum aestivwn) were treated with postemergence applications of test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant. Plants were treated at the 2-3 leaf stage and 2 whorl stage for wheat and catchweed bedstraw, respectively. Treated plants and controls were maintained in a controlled growth environment for 15 days after which time all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table K, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result. Table K - Results from Treatment of Wheat and Sulfonylurea Susceptible and Resistant Catchweed Bedstraw with Compounds 1 and 9 and Chlorsulfuron Application Rate (g a.i^ha) Compound 1 (Table Removed) As can be seen from Table K, while chlorosulfuron had little effect on the sulfonylurea-resistant biotype of Galium aparine in this test, Compounds 1 and 9 gave good control of both resistant and susceptible biotypes. This field study included treatments that consisted of Compound 1 and nicosulfuron alone and in combination on Canada thistle (Cirsium arvense) and daisy fleabane (Erigeron spp.). The plants ranged from 20 to 30 cm in height at the lime of application during the month of May in the vicinity of Newark, Delaware. Compound 1 was formulated as a wettable powder containing 25% active ingredient by weight. Nicosulfuron was in the form of Accent® Herbicide, a water-dispersible granule formulation containing 75% active ingredient by weight. The formulations were dispersed in water in the sprayer tank before treatment. The treatments were made using a backpack sprayer calibrated to deliver 24 gallons per acre (224 L per hectare) to a 10 ft x 30 ft (3 m x 9 m) plot. Each treatment was replicated two times. The effects on the plants approximately 56 days after treatment were visually compared to untreated controls. Plant response ratings were calculated as the means of the two replicates, based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. Colby's Equation was used to determine the herbicidal effects expected from the mixture. The results and additive effects expected from Colby's Equation are listed in Table L. Table L - Observed (Obsd.) and Expected (Exp.) Results from Compound 1 Alone and in Combination with Nicosulfuron* Application Rate (g a.i Jha) Compound 1 (Table Removed) * Application rates are grams of active ingredient per hectare (g a.i7ha). "Obsd." is observed effect. "Exp." is expected effect calculated from Colby's Equation. Table L shows that a synergistic effect was apparent in this test from the combination of compound 1 and nicosulfuron. CLAIMS What is claimed is: 1. A compound selected from Formula I, an TV-oxide or an agriculturally suitable salt thereof, (Figure Removed )I wherein R1 is cyclopropyl optionally substituted with 1-5 R5, isopropyl optionally substituted with 1-5 R6, or phenyl optionally substituted with 1-3 R7; R2 is((0)jC(Rl5)(Rl6))kR; R is C02H or a herbicidally effective derivative of C02H; R3.-is halogen, cyano, nitro, OR20, SR21 or N(R22)R23; R4 is-N(R24)R25 or-N02; each R5 and R6 is independently halogen, C1--C6 alkyl, C1--C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C1-C3 alkoxy, C1-C2 haloalkoxy, C1C3, alkylthio or C1~C2 haloalkylthio; each R7 is independently halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C1- C4 hydroxyalkyl, C2-C4 alkoxyalkyl, C2-C4 haloalkoxyalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C3-C4 alkynyl, C3-C4 haloalkynyl, hydroxy, C1~C4 alkoxy, C^-C^ haloalkoxy, C2-C4 alkenyloxy, C2-C4 haloalkenyloxy, C3-C4 alkynyloxy, C3-C4 haloalkynyloxy, C!-C4 alkylthio, C!-C4 haloalkylthio, C1-C4. alkylsulfinyl, C1-C4 haloalkylsulfinyl, C^-C^ alkylsulfonyl, C^-C.^ haloalkylsulfonyl, C2-C4 alkenylthio, C2-C4 haloalkenylthio, C2-C4 alkenylsulfinyl, C2-C4 haloalkenylsulfmyl, C2-C4 alkenylsulfonyl, C2-C4 haloalkenylsulfonyl, C3-C4 alkynylthio, C3-C4 haloalkynylthio, C3-C4 alkynylsulfmyl, C3-C4 haloalkynylsulfmyl, C3-C4 alkynylsulfonyl, C3-C4 haloalkynylsulfonyl, 0^4 allcylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C^-C^ (alkyl)cycloalkylamino, C2-C6 alkylcarbonyl, C2-Cg alkoxycarbonyl, C2-C6 alkylaminocarbpnyl, C3-C8 dialkylaminocarbonyl, C3-C6 trialkylsilyl, phenyl, phenoxy and 5- or 6-membered heteroaromatic rings, each phenyl, phenoxy and 5- or 6-membered heteroaromatic ring optionally substituted with one to three substituents independently selected from R45; or two adjacent R7 are taken together as -OCH2O-, -CH2CH2O-, -OCH(CH3)O-, -OC(CH3)20-, -OCF2O-, -CF2CF2O-, -OCF2CF20- or -CH=CH-CH=CH-; R15 is H, halogen, Ci-C4 alkyl, Cj-C,^ haloalkyl, hydroxy, C]-C4 alkoxy or C2-C4 alkylcarbonyloxy; R16 is H, halogen, C^-C^ alkyl or CpC* haloalkyl; or R15 and R16 are taken together as an oxygen atom to form, with the carbon atom to which they are attached, a carbonyl moiety; R20 is H, ^-€4 alkyl or C^ haloalkyl; R21 is H, C!-C4 alkyl or CpC^ haloalkyl; R22 and R23 are independently H or Cj-C4 alkyl; R24 is H, CJ-C4 alkyl optionally substituted with 1-2 R30, C2-C4 alkenyl optionally substituted with 1-2 R31, or C2~C4 alkynyl optionally substituted with 1-2 R32; or R24 is C(=0)R33, nitro, OR34, S(O)2R35, N(R36)R3? or N=C(R62)R63; R25 is H, C!-C4 alkyl optionally substituted with 1-2 R30 or C(=O)R33; or R24 and R25 are taken together as a radical selected from -(CH2)4-, -(CH^-, -CH2CH=CHCH2- and -(CH^CXCH^-, each radical optionally substituted with 1-2 R38; or R24 and R^ are taken together as =C(R39)N(R4C))R41 or =C(R42)OR43; each R30, R31 and R32 is independently halogen, Ci~C3 alkoxy, C!-C3 haloalkoxy, CI-CT, alkylthio, Cj-C3 haloalkylthio, amino, Cj-C3 alkylamino, C2-C4 dialkylamino or C2-C4 alkoxycarbonyl; :each R33 is independently H, Cj-C^ alkyl, Ci~Cj haloalkyl, C^-C^ alkoxy, phenyl, phenoxy or benzyloxy; R34 is H, CrC4 alkyl, Cj-C3 haloalkyl or CHR66c(0)OR67; R35 is Cj-C4 alkyl or C^-Cs haloalkyl; R36 is H, CrC4 alkyl or C(=O)'R.^; R3? is H or C!-C4 alkyl; each R38 is independently halogen, Cj,-C3 alkj'l, Ci-C3 alkoxy, Ci~C^ haloalkoxy, CJ-C3 alkylthio, Cj-C3 haloalkylthio, amino, Cj-C3 alkylamino, C2-C4 dialkylamino or C2-C4 alkoxycarbonyl; R3^ is H or C{-C4 alkyl; R40 and R41 are independently H or Ci~C4 alkyl; or R40 and R41 are taken together as -(CH2)4-, -(CH2)s-. -CH2CH=CHCH2- or R43 is C!-C4 alkyl; ' each R45 is independently halogen, cyano, nitro, Cj-C4 alkyl, C^-C^ haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C3-C4 alkynyl, C3-C4 haloalkynyl, C1-C4 alkoxy, C1 C4 haloalkoxy, C1-C4 alkylthio, C1-C4 haloalkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, CrC4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C4-C6 (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2 C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl or C3-C6 trialkylsilyl; R62 is H, C1-C4 alkyl or phenyl optionally substituted with 1-3 R65; R63 is H or C1-C4 alkyl; or R62 and R63 are taken together as -(CH2)4- or -(CH2)5-; R64 is H, C1-C14 alkyl, C1-C3 haloalkyl, C1~C4 alkoxy, phenyl, phenoxy or benzyloxy; each R65 is independently CH3, Cl or OCH3; R66 is H, C1-C4 alkyl or C1-^ alkoxy; R67 isH, Ci-C4 alkyl or benzyl; j is 0 or 1; and k is 0 or 1; provided that: (a) when k. is 0, then j is 0; (b) when R2 is CH2ORa wherein R is H, optionally substituted alkyl or benzyl, then R3 is other than cyano; (c) when R1 is phenyl substituted by Cl in each of the meta positions, the phenyl is also substituted by R7 in the para position; (d) when R1 is phenyl substituted by R7 in the para position, said R7 is other than tert-butyl, cyano or optillonay substituted phenyl; (e) when R1 is cyclopropyl or isopropyl optionally substituted with 1-5 R6, then R is other than C(=W)N(Rb)S(0)2-Rc-Rd wherein W is 0, S, NRe or NORe; Rb is hydrogen, C1~C4 alkyl, C2-C6 alkenyl or C2-C 6alkynyl; Rc is a direct bond or CHRf, O, NRe or NORe; Rd is an optionally substituted heterocyclic or carbocyclic aromatic radical having 5 to 6 ring atoms, the radical being optionally condensed with an aromatic or nonaromatic 5- or 6-membered ring; each Re is independently H, C1-C3 alkyl, C1-C3 haloalkyl or phenyl; and Rf is H, C1-C3 alkyl or phenyl; and (f) the compound of Formula I is other than diethyl 6-arnino-5-nitro-2-phenyl- 4-pyrimidinemalonate. 2. The compound of Claim 1 wherein R2 is C02R12, CH2OR13, CH(OR46)(OR47), CHO, C(=NORl4)H, C(=NNR48R49)H, (0)jC(Rl5)(Rl6)C02R17, C(=0)N(R18)R19, C(=S)OR50, C(=0)SR51, C(=S)SR52 or C(=NR53)YR54; R12 is H, -CH{C(0)0(CH2)m}, -N=C(R55)R56; or a radical selected from C1-C14 alkyl, C3-C12 cycloalkyl, C4-C12 alkylcycloalkyl, C4-C12 cycloalkylalkyl, C2~C14 alkenyl, C2-C14 alkynyl and phenyl, each radical optionally substituted with 1-3 R27; or R12 is a divalent radical linking the carboxylic ester function CO2R12 of each of two pyrimidine ring systems of Formula I, the divalent radical selected from -CH2-, -(CH2)2-, -(CH2)3- and -CH(CH3)CH2-; R13 is H, C1-C10 alkyl optionally substituted with 1-3 R28, or benzyl; R14 is H, C1-C4 alkyl, C1-C4 haloalkyl or benzyl; R17 is CI-CIQ alkyl optionally substituted with 1-3 R29, or benzyl; R18 is H, C1-C4 alkyl, hydroxy, Cj-C4 alkoxy or SCO2R57; R19isHorC!-C4alkyl; each R27 is independently halogen, cyano, hydroxycarbonyl, C2-C4 alkoxycarbonyl, hydroxy, C1-C4 alkoxy, C1-C4 haloalkoxy, C1~C4 alkylthio, C1-C4 haloalkylthio, amino, C1 - C4 alkylamino, C2-C4 dialkylamino, -CH£0(CH2)n} or phenyl optionally substituted with 1-3 R44; or two R27 are taken together as -OC(0)0- or -O(C(R58)(R58))!_2O-; or two R27 are taken together as an oxygen atom to form, with the carbon atom to which : they are attached, a carbonyl -moiety; each R28is independently halogen, Cj-C4 alkoxy, Ci~C4 haloalkoxy, C]-C4 alkylthio, (C1 C4 haloalkylthio, amino, C1-C4 alkylamino or C2-C4 dialkylamino; or two R28 are taken together as an oxygen atom to form, with the carbon atom to which they are attached, a carbonyl moiety; each R29 is independently halogen, C1-C4 alkoxy, C1-C4 haloalkoxy, C1~C4 alkylthio, (C1-C4 haloalkylthio, amino, C1-C4 alkylamino or C2-C4 dialkylamino; each R44 is independently halogen, Cj-C4 alkyl, Cj-C3 haloalkyl, hydroxy, C!-C4 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, C1~C3 haloalkylthio, amino, C1-C3 alkylamino, C2-C4 dialkylamino or nitro; R46 and R47 are independently (^-€4 alkyl or C^-C3 haloalkyl; or R46 and R47 are taken together as -CH2CH2-, -CH2CH(CH3)- or -(CH2)3-; R48 is H, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkylcarbonyl, C2-C4 alkoxycarbonyl or benzyl; R49 is H, C1-C4 alkyl or C-1C4 haloalkyl; R50, R51 and R52 are H; or a radical selected from C1-C14 alkyl, C3-C12 cycloalkyl, C4-C12 alkylcycloalkyl, C4-C12 cycloalkylalkyl, C2-C14 alkenyl and C2-C14 allcynyl, each radical optionally substituted with 1-3 R27; YisO.SorNR61; R53 is H, C1-C3 alkyl, C1-Cs haloalkyl, C2C4 alkoxyalkyl, OH or C1C3 alkoxy; R54 is C}-C3 alkyl, C1-Cs haloalkyl or C2-C4 alkoxyalkyl; or R53 and R54 are taken together as -(CH2)2-, -CH2CH(CH3)- or -(CH2)3-; R55 and R56 are independently Cj-C4 alkyl; R57 is C1-04 alkyl, C1C3 haloalkyl orNR59R6°; each R58 is independently selected from H and C1-C4 alkyl; R59 and R60 are independently H or C1-C4 alkyl; R61 is H, C!-C3 alkyl, CpCs haloalkyl or C2-C4'alkoxyalkyl; m is an integer from 2 to 3; and n is an integer from 1 to 4. 3. The compound of Claim 2 wherein R3 is halogen. 4. The compound of Claim 2 wherein R1 is cyclopropyl or phenyl substituted with a halogen, methyl or methoxy radical in the para position and optionally with 1-2 radicals selected from halogen and methyl in other positions; and R4 is -N(R24)R25. 5. The compound of Claim 4 wherein R2 is CO2R12, CH2OR13, CHO or CH2C02R17. 6. The compound of Claim 5 wherein R24 is H, C(O)R33 or C1-^ alkyl optionally substituted with R30; R25 is H or C1-C2 alkyl; or R24 and R25 are taken together as =C(R39)N(R40)R41. 7. The compound of Claim 6 wherein R2 is CO2R12; and R24 and R25 are H. 8. The compound of Claim 7 wherein R12 is H, C!-C4 alkyl or benzyl. 9. The compound of Claim 1 selected from the group consisting of: methyl 6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylate, ethyl 6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylate, phenylmethyl 6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylate, 6-amino-5-bromo-2-cyclopropyl-4-p}Timidinecarboxylic acid monosodium salt, methyl 6-amino-5-chloro'-2-cyclopropyl-4-pyrimidinecarboxylate, phenylmethyl 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylate, 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid monosodium salt, ethyl 6-amino-5-chloro-2-cyclopropyl-4-pyrirnidinecarboxylate, methyl 6-amino-5^hloro-2-(4-chlorophenyl)-4-pyrunidinecarboxylate, ethyl 6-amino-5^hloro-2-(4-chlorophenyl)-4-pyriinidinecarboxylate) 6-amino-5-chloro-2-(4-chlorophenyl)-4-pyrimidinecarboxylic acid, ethyl 6-amino-2-(4-bromophenyl)-5-chloro-4-pyrimidinecarboxylate, methyl 6-amino-2-(4-bromophenyl)-5-chloro-4-pyrimidinecarboxylate, and 6-amino-2-(4-bromophenyl)-5-chloro-4-pyrimidinecarboxylic acid. 10. A herbicidal mixture comprising a herbicidally effective amount of a compound of Claim 1 and an effective amount of at least one additional active ingredient selected from the group consisting of an other herbicide and a herbicide safener. 11. A herbicidal mixture comprising synergistically effective amounts of a compound of Claim 1 and an auxin transport inhibitor. 12. A herbicidal composition comprising a herbicidally effective amount of a compound of Claim 1 and at least one of a surfactant, a solid diluent or a liquid diluent. 13. A method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with a herbicidally effective amount of a compound of Claim 1. 14. A herbicidal composition comprising a herbicidally effective amount of a compound of Claim 1, an effective amount of at least one additional active ingredient selected from the group consisting of an other herbicide and a herbicide safener, and at least one of a surfactant, a solid diluent or a liquid diluent. 15. A compound which is 2-cyclopropyl-l ,6-dihydro-6-oxo-4-pyrimidinecarboxylic acid. 16. A compound which is 5-chloro-2-cyclopropyl-1.6-dihydro-6-oxo-4-pyrimidine- carboxylic acid. 17. A compound which is 5,6-dichloro-2-cyclopropy!-4-pyrimidinecarboxylic acid. 18. The compound of Claim 1 selected from the group consisting of: methyl 6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylate, ethyl 6-arnino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylate, phenylmethyl 6-amino-5-bromo-2-cyclopropyl-4-pyrimidmecarboxylate, 6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylic acid monosodium salt, 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid, methyl 6-amino-5-chloro-2-cyclopropyl-4-pryimidmecarboxylate, phenylmethyl 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylate, AMENDED SHEET 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxyIic acid monosodium salt, 6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylicacid, ethyl 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylate, methyl 6-amino-5-chloro-2-(4-chlorophenyl)-4-pyrimidinecarboxylate, ethyl 6-amino-5-chloro-2-(4-chlorophenyl)-4-pyrimidinecarboxylate, 6-amino-5-chloro-2-(4-chlorophenyl)-4-pyrimidinecarboxylic acid, ethyl 6-arnmo-2-(4-bromophenyl)-5-chloro-4-pyrirnidinecarboxylate. methyl 6-amino-2-(4-broraophenyl)-5-chloro-4-pyrimidinecarboxylate, and 6-amino-2-(4-bromophenyl)-5-chloro-4-pyrimidinecarboxylic acid. 19. The compound of claim 18 selected from the group consisting of: ethyl 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylate, methyl 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylate, methyl 6-amino-5-chloro-2-(4-chlorophenyl)-4-pyrimidinecarboxylate, ethyl 6-amino-5-chloro-2-(4-chlorophenyl)-4-pyrimidinecarboxylate, 6-amino-5-chIoro-2-(4-chlorophenyl)-4-pyrimidinecarboxylic acid, ethyl 6-amino-2-(4-bromophenyl)-5-chloro-4-pyrimidinecarboxylate, 6-amino-2-(4-bromophenyl)-5-chloro-4-pynmidinecarboxylic acid, methyl 6-amino-2-(4-bromophenyl)-5-chloro-4-pyrimidinecarboxylate, and 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid. 20. A compound of claim 1 which is 6-amino-5-bromo-2-cyclopropyl-4- pyrimidinecarboxylic acid. 21. A compound of claim 1 which is methyl 6-amino-5-bromo-2-cyclopropyl-4- pyrimidinecaiboxylate. 22. A compound of claim Iwhich is methyl 6-amino-5-chloro-2-(4-chlorophenyl)-4- pyrimidinecarboxylate. 23. A compound of claim 1 which is ethyl 6-amino-5-chloro-2-(4-chlorophenyl)-4- pyrimidinecarboxylate. 24. A compound of claim 1 which is 6-amino-5-chloro-2-(4-chlorophenyl)-4- pyrimidinecarboxylic acid. AMENDED SHEET 25. A compound of claim 1 which is 6-amino-5-chloro-2-cyclopropyl-4- pyrimidinecarboxylic acid. 26. A compound of claim 1 which is ethyl 6-amino-5-bromo-2-cyclopropyl-4- pyrimidinecarboxylate. 27. A compound of claim 1 which is methyl 6-amino-5-chloro-2-cyclopropyl-4- pyrimidinecarboxylate. 28. A compound of claim 1 which is ethyl 6-amino-5-chloro-2-cyclopropyl-4- pyrimidinecarboxylate. 29. A herbicidal mixture comprising a herbicidally effective amount of a compound of claims 18 or 19, and an effective amount of at least one additional active ingredient selected from the group consisting of an other herbicide and a herbicide safener. 30. The herbicidal mixture of claim 10 wherein the additional active ingredient is selected from the group consisting of: amidosulfuron, azimsulfuron, bensulfuron-methyl, bispyribac, bispyribac-sodium, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cloransulam-methyl, cyclosulfamuron, diclosulam, ethametsulfuron-methyl, ethoxysulfuron, flazasulfiiron, florasulam, flucarbazone, flucarbazone-sodium, flucetosulfuron, flumetsulam, flupyrsulfuron-methyl, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron-methyl, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazaquin-ammonium, imazethapyr, imazosulfuron, iodosulfuron-methyl, mesosulfuron-methyl, metosulam, metsulfuron-methyl, nicosulfuron, oxasulfuron, penoxsulam, primisulfuron-methyl, propoxycarbazone, propoxycarbazone-sodium, prosulfuron, pyrazosulfuron-ethyl, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron-methyl, triasulfuron, tribenuron-methyl, trifloxysulfuron, tnflusulfuron-methyl and tritosulfuron. 31. The herbicidal mixture of claim 30 wherein the additional active ingredient is in combination with at least one other active ingredient to form a combination of active ingredients selected from the group consisting of: chlorsuifuron and flucarbazone-sodium; chlorsulfuron and sulfometuron-methyl; flumetsulam, nicosulfuron and rimsulfuron; mesosulfuron-methyl and iodosulfuron-methyl; metsulfuron-methyl and chlorsulfuron; AMENDED SHEET metsulfuron-methyl and sulfometuron-methyl; metsulfuron-methyl, thifensulfuron-methyl and tribenuron-methyl; imazapyr and metsulfuron-methyl; imazapyr, metsulfuron-methyl and sulfometuron-methyl; imazapyr and sulfometuron-methyl; rimsulfuron and nicosulfuron; rimsulfuron and thifensulfuron-methyl; thifensulfuron-methyl and metsulfuron-methyl; tribenuron-methyl and metsulfuron-methyl; tribenuron-methyl and thifensulfuron-methyl; bensulfuron-methyl and metsulfuron-methyl; and metsulfuron-methyl and chlorimuron-ethyl. 32. The herbicidal mixture of claim 29 wherein the additional active ingredient is selected from the group consisting of: amidosulfuron, azimsulfuron, bensulfuron-methyl, bispyribac, bispyribac-sodium, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cloransulam-methyl, cyclosulfamuron, diclosulam, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, florasulam, flucarbazone, flucarbazone-sodium, flucetosulfuron, flumetsulam, flupyrsulfuron-methyl, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron-methyl, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazaquin-ammonium, imazethap>T, irnazosulfuron, iodosulfuron-methyl, mesosulfuron-methyl, metosulam, metsulfuron-methyl, nicosulfuron, oxasulfuron, penoxsulam, primisulfuron-methyl, propoxycarbazone, propoxycarbazone-sodium, prosulfuron, pyrazosulfuron-ethyl, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron-methyl, triasulfuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron-methyl and tritosulfuron. 33. The herbicidal mixrure of claim 32 wherein the additional active ingredient is in combination with at least one other active ingredient to form a combination of active ingredients selected from the group consisting of: chlorsulfuron and fiucarbazone-sodium; chlorsulfuron and sulfometuron-methyl; flumetsulam, nicosulfuron and rimsulfuron; AMENDED SHEET mesosulfuron-methyl and iodosulfuron-methyl; metsulfuron-methyl and chlorsulfuron; metsulfuron-methyl and sulforneturon-methyl; metsulfuron-methyl, thifensulfuron-methyl and tribenuron-methyl; imazapyr and metsulfuron-methyl; imazapyr, metsulfuron-methyl and sulfometuron-methyl; imazapyr and sulfometuron-methyl; rimsulfuron and nicosulfuron; rimsulfuron and thifensulfuron-methyl; thifensulfuron-methyl and metsulfuxon-methyl; tribenuron-methyl and metsulfuron-methyl; tribenuron-methyl and thifensulfuron-methyl; bensulfuron-methyl and metsulfuron-methyl; and metsulfuron-methyl and chlorimuron-ethyl. 34. A herbicidal mixture comprising synergistically effective amounts of a compound of either of claims 18 or 19 and an auxin transport inhibitor. 35. The herbicidal mixture of claim 11 wherein the compound is selected from the group consisting of: ethyl 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylate, methyl 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylate, methyl 6-amino-5-chloro-2-(4-chlorophenyl)-4-p>'rimidinecarboxylate, ethyl 6-amino-5-chloro-2-(4-chlorophenyl)-4-pyrimidinecarboxylate, 6-amino-5-chloro-2-(4-chlorophenyl)-4-pyrimidinecarboxylic acid, ethyl 6-amino-2-(4-bromophenyl)-5-chloro-4-pyrimidinecarboxylate, 6-amino-2-(4-bromophenyI)-5-chloro-4-pyrimidinecarboxylic acid, methyl 6-amino-2-(4-bromophenyl)-5-chloro-4-p\Timidinecarboxylate and 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid, and the auxin transport inhibitor is diflufenzopyr. AMENDED SHEET 36. The herbicidal mixture of claim 11 wherein the compound is ethyl 6-amino-5- bromo-2-cyclopropyl-4-pyrimidinecaiboxylate and the auxin transport inhibitor is diflufenzopyr. 37. The herbicidal mixture of claim 29 further comprising at least one of a surfactant, a solid diluent or a liquid diluent. 38. The herbicidal mixture of claim 34 further comprising at least one of a surfactant, a solid diluent or a liquid diluent. 39. The herbicidal mixture of claim 37 wherein the additional active ingredient is selected from the group consisting of: amidosulfuron, azimsulfuron, bensulfuron-methyl, bispyribac, bispyribac-sodium, chlorimuron-ethy], chlorsulfuron, cinosulfuron, cloransulam-methyl, cyclosulfamuron, diclosulam, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, florasulam, flucarbazone, flucarbazone-sodium, flucetosulfuron, flumetsulam, flupyrsulfuron-methyl, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron-methyl, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazaquin-ammonium, imazethapyr, imazosulfuron, iodosulfuron-methyl, mesosulfuron-methyl, metosulam, metsulfuron-rnethyl, nicosulfuron, oxasulfuron, penoxsulam, primisulfuron-methyl, propoxycarbazone, propoxycarbazone-sodium, prosulfuron, pyrazosulfuron-ethyl, pyribenzoxim, pyriftalid, pyriminobac-methy], pyrithiobac, pyrithiobac-sodium, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron-methyl, triasulfuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron-methyl and tritosulfuron. 40. The herbicidal mixture of claim 39 wherein the additional active ingredient is in combination with at least one other active ingredient to form a combination of active ingredients selected from the group consisting of: chlorsulfuron and flucarbazone-sodium; chlorsulfuron and sulfometuron-methyl; flumetsulam, nicosulfuron and rimsulfuron; mesosulfuron-methyl and iodosulfuron-methyl; metsulfuron-methyl and chlorsulfuron; metsulfuron-methyl and sulfometuron-methyl; metsulfuron-methyl, thifensulfuron-methyl and tribenuron-methyl; imazapyr and metsulfuron-methyl; imazapyr, metsulfuron-methyl and sulfometuron-methyl; AMENDED SHEET imazapyr and sulfometuron-methyl; rimsulfuron and nicosulfuron; rimsulfuron and thifensulfuron-methyl; thifensulfuron-methyl and metsulfiiron-methyl; tribenuron-methyl and metsulfuron-methyl; tribenuron-methyl and thifensulfuron-methyl; bensulfuron-methyl and metsulfuron-methyl; and metsulfuron-methyl and chlorimuron-ethyl. 41. The herbicidal mixture of claim 32 wherein the mixture has a greater than additive effect on weeds or a less than additive effect on crops or other desirable plants. 42. The herbicidal mixture of claim 33 wherein the mixture has a greater than additive effect on weeds or a less than additive effect on crops or other desirable plants. 43. A method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with the herbicidal mixture of claim 32. 44. A method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with the herbicidal mixture of claim 33. 45. A method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with the herbicidal mixture of claim 34.

Documents:

3045-delnp-2006-Abstract-(05-10-2012).pdf

3045-delnp-2006-abstract.pdf

3045-delnp-2006-Claims-(05-10-2012).pdf

3045-delnp-2006-claims.pdf

3045-delnp-2006-Correspondence Others-(04-04-2012).pdf

3045-delnp-2006-Correspondence Others-(11-04-2013).pdf

3045-DELNP-2006-Correspondence Others-(16-11-2011).pdf

3045-delnp-2006-Correspondence-Others-(05-10-2012).pdf

3045-delnp-2006-Correspondence-Others-(08-10-2012).pdf

3045-delnp-2006-correspondence-others-1.pdf

3045-delnp-2006-correspondence-others.pdf

3045-delnp-2006-description (complete).pdf

3045-delnp-2006-form-1.pdf

3045-delnp-2006-Form-13-(05-10-2012).pdf

3045-delnp-2006-form-18.pdf

3045-delnp-2006-form-2.pdf

3045-delnp-2006-Form-3-(04-04-2012).pdf

3045-delnp-2006-Form-3-(05-10-2012).pdf

3045-delnp-2006-Form-3-(11-04-2013).pdf

3045-delnp-2006-form-3.pdf

3045-delnp-2006-form-5.pdf

3045-DELNP-2006-GPA-(16-11-2011).pdf

3045-delnp-2006-gpa.pdf

3045-delnp-2006-pct-101.pdf

3045-delnp-2006-pct-210.pdf

3045-delnp-2006-pct-220.pdf

3045-delnp-2006-pct-237.pdf

3045-delnp-2006-pct-304.pdf

3045-delnp-2006-pct-409.pdf

3045-delnp-2006-pct-416.pdf

3045-delnp-2006-Petition-137-(05-10-2012).pdf

3045-delnp-2006-Petition-138-(05-10-2012).pdf