Title of Invention

A FUNGICIDAL COMPOSITION

Abstract A fungicidal composition comprising: (1) at least one quinazolinone of Formula 1 including all geometric and stereoisomers, N-oxides, and agriculturally suitable salts thereof, wherein D is O or S; R1 is C1-C6 alkyl; R2 is C1-C6 alkyl; R3 is halogen; and R4 is hydrogen or halogen; (2) at least one component which is at least one compound selected from compounds that controls fungal disease by inhibiting the sterol biosynthesis and optionally (3) at least one of a surfactant, a solid diluent or a liquid diluent; wherein component (1) and component (2) are present in fungicidally effective amount and the mole ratio of component (1) to component (2) is from 30:1 to 1:30.
Full Text TITLE
FUNGICIDAL MIXTURES
BACKGROUND OF THE INVENTION
Fungicides that effectively control plant diseases are in constant demand by
growers. Plant diseases are highly destructive, difficult to control and quickly develop
resistance to commercial fungicides. Combinations of pesticides are often used to
facilitate disease control, to broaden spectrum of control and to retard resistance
development. It is recognized in the art that the advantages of particular pesticide
combinations can often vary, depending on such factors as the particular plant and plant
disease to be treated, and the treatment conditions. Accordingly, there is an ongoing
search for advantageous combinations of pesticides.
International Patent Application WO 94/26722 discloses certain quinazolinone
compounds as fungicides (e.g., 6-bromo-3-propyl-2-propyloxy-4(3H)-quinazolinone,
6,8-diiodo-3-propyl-2-propyloxy-4(3H)-quinazolinone and 6-iodo-3-propyl-2-
propyloxy-4(3H)-quinazolinone). International Patent Application WO 95/14009
discloses certain triazolone fungicides (e.g., 2,4-dihydro-5-methoxy-2-methyl-4-[2-
[[[[1-[3-(trifluoromethyl)phenyl]ethylidene]amino]oxy]-methyl]phenyl]-3H-1,2,4-
triazol-3-one). Kresoxim-methyl (BAS 490F) is a fungicide under consideration for the
control of plant diseases, especially fungal diseases of wheat, grapes and fruits. (See E.
Ammermann, G. Lorenz, K. Schelberger, B. Wenderoth, H. Sauter and C. Rentzea
"BAS 490F - A Broad-Spectrum Fungicide with a New Mode of Action" in Brighton
Crop Protection Conference - Pests and Diseases -1992, 1, 403-410.) Azoxystrobin
(ICIA5504) is a fungicide under consideration for the control of plant diseases on a wide
range of crops. (See J. R. Godwin, V. M. Anthony, J. M. Clough and C. R. A. Godfrey
"ICIA5504: A Novel, Broad Spectrum, Systemic p-Methoxyacrylate Fungicide" in
Brighton Crop Protection Conference - Pests and Diseases -1992,1,435-442.)
European Patent Application EP-A-398,692 discloses (E)-2-(memoxyimino)-N-methyl-
2-(2-phenoxyphenyl)acetamide also known as SSF 126. This fungicide is under
consideration for the control of plant disease, especially of rice. EP-A-68813 discloses
certain triazole compounds as fungicides (e.g., flusilazole). EP-A-40345 discloses
certain triazole compounds as fungicides (e.g., tebuconazole).
SUMMARY OF THE INVENTION
This invention is directed to fungicidal combinations (e.g., mixtures) comprising
(1) at least one compound selected from the quinazolinones of Formula I (including all
geometric and stereoisomers), N-oxides, and agriculturally suitable salts thereof,

wherein
D is O or S;
R1 is C,-C10 alkyl; C3-C5 cycloalkyl; C3-C10 alkenyl; C3-C10 alkynyl;
C1-C10 haloalkyl; C3-C10 haloalkenyl; C3-C10 haloalkynyl;
C2-C10 alkoxyalkyl; C2-C10 alkylthioalkyl; C2-C10 alkylsulfinylalkyl;
C2-C10 alkylsulfonylalkyl; C4-C10 cycloalkylalkyl;
C4-C10 alkenyloxyalkyl; C4-C10 alkynyloxyalkyl; C4-C10
(cycloalkyl)oxyalkyl; C4-C10 alkenylthioalkyl; C4-C10 alkynylthioalkyl;
C4-C10 (cycloalkyl)thioalkyl; C2-C10 haloalkoxyalkyl;
C4-C10 haloalkenyloxyalkyl; C4-C10 haloalkynyloxyalkyl;
C4-C10 alkoxyalkenyl; C4-C10 alkoxyalkynyl; C4-C10 alkylthioalkenyl;
C4-C10 alkylthioalkynyl; C4-C10 trialkylsilylalkyl; C1-C10 alkyl substituted
with NR5R6, nitro, cyano or phenyl optionally substituted with R8, R9 and
R10; C1-C10 alkoxy; C1-C10 haloalkoxy; C1-Cl0 alkylthio;
C1-C10 haloalkylthio; or pyridinyl, furanyl, thienyl, naphthalenyl,
benzofuranyl, benzothienyl or quinolinyl each optionally substituted with
R8, R9 and R10;
R2 is C1-C10 alkyl; C3-C7 cycloalkyl; C3-C10 alkenyl; C3-C10 alkynyl;
C1-C10 haloalkyl; C3-C10 haloalkenyl; C3-C10 haloalkynyl;
C2-C10 alkoxyalkyl; C2-C10 alkylthioalkyl; C2-C10 alkylsulfinylalkyl;
C2-C10 alkylsulfonylalkyl; C4-C10 cycloalkylalkyl;
C4-C10 alkenyloxyalkyl; C4-C10 alkynyloxyalkyl; C4-C10
(cycloalkyl)oxyalkyl; C4-C10 alkenylthioalkyl; C4-C10 alkynylthioalkyl;
C4-C10 (cycloalkyl)thioalkyl; C2-C10 haloalkoxyalkyl;
C4-C10 haloalkenyloxyalkyl; C4-C10 haloalkynyloxyalkyl;
C4-C10 alkoxyalkenyl; C4-C10 alkoxyalkynyl; C4-C10 alkylthioalkenyl;
C4-C10 alkylthioalkynyl; C4-C10 trialkylsilylalkyl; C2-C10 cyanoalkyl;
C1-C10 nitroalkyl; C1-C10 alkyl substituted with CO2R5, NR5R6, or phenyl
optionally substituted with R7, R9 and R10; phenyl optionally substituted
with R7, R9 and R10; -N=CR5R5; or -NR5R6; or
R1 and R2 are taken together to form -CH2(CH2)qCH2-;
q is 0, 1,2, 3 or 4;
R3 is halogen, C1-C8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl, C2-C8 alkynyl,
C1-C8 haloalkyl, C3-C8 haloalkenyl, C3-C8 haloalkynyl, C1-C8 alkoxy,
C1-C8 haloalkoxy, C3-C8 alkenyloxy, C3-C8 alkynyloxy, C1-C8 alkylthio,
C3-C8 alkenylthio, C3-C8 alkynylthio, C1-C8 alkylsulfinyl, C1-C8
alkylsulfonyl, C2-C8 alkoxyalkyl, C2-C8 alkylthioalkyl,
C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C4-C8 cycloalkylalkyl,
C3-C8 trialkylsilyl, NR5R6, C5-C8 trialkylsilylalkynyl or phenyl optionally
substituted with at least one R7;
R4 is hydrogen, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or
C1-C4 haloalkoxy;
each R5 is independently hydrogen, C1-C4 alkyl or phenyl optionally substituted
with at least one R7;
each R6 is independently hydrogen, C1-C8 alkyl or phenyl optionally substituted
with at least one R7; or
when R5 and R6 are attached to the same nitrogen atom, R5 and R6 can be taken
together to form -CH2CH2CH2CH2-, -CH2(CH2)3CH2-,
-CH2CH2OCH2CH2-, -CH2CH(Me)CH2CH(Me)CH2- or
-CH2CH(Me)OCH(Me)CH2-;
each R7 is independently halogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkyl,
nitro or cyano;
R8 is C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, halogen, C2-C8 alkynyl,
C1-C6 alkylthio, phenyl or phenoxy each optionally substituted with at least
one R7, cyano, nitro, C1-C6 haloalkoxy, C1-C6 haloalkylthio, C2-C6
alkenyl, C2-C6 haloalkenyl, acetyl, CO2Me or N(C1-C2 alkyl)2;
each R9 is independently methyl, ethyl, methoxy, methylthio, halogen or
trifluoromethyl; and
each R10 is independently halogen;
and (2) at least one compound selected from (a) compounds acting at the bc\ complex of
the fungal mitochondrial respiratory electron transfer site and (b) compounds that
control fungal disease by inhibiting the sterol biosynthesis pathway. This invention
provides agricultural compositions containing these combinations and the use of the
combinations as fungicides. Advantageous compositions include those where
component (1) and component (2) are present in a fungicidally effective amount and the
mole ratio of component (1) tocomponent (2) is from about 30:1 to 1:30.
Advantageous methods include those where component (I) and component (2) are
added in amounts sufficient to provide a fungicidal effectiveness greater than the sum of
the fungicidal effectivenesses provided by those amounts of said components taken
independently.
DETAILS OF THE INVENTION
Combinations of fungicides are used in accordance with this invention to facilitate
disease control and to retard resistance development. Suitable compositions and
methods are provided.
For example, this invention also provides methods for controlling plant diseases
caused by fungal plant pathogens comprising applying to the plant or portion thereof to
be protected, or to the plant seed or seedling to be protected one of the following:
A) an effective amount of a fungicidal composition comprising component (1),
component (2), and at least one of a surfactant, a solid diluent or a liquid diluent;
B) (i) an effective amount of a first composition comprising component (1), and
at least one of a surfactant, solid or liquid diluent; and (ii) an effective amount of a
second composition comprising component (2), and at least one of a surfactant, a solid
diluent or a liquid diluent; said first and second compositions applied sequentially in
any order; or
C) an effective amount of a physical mixture of the first and second compositions
as defined in B above.
The mole ratio of the compound(s) of component (1) to the compound(s) of
component (2) applied is normally from about 30:1 to 1:30, and the compound(s) of
component (1) and the compound(s) of component (2) are normally applied in amounts
effective to provide control of the fungal disease which is greater than the additive
control of that fungal disease provided by the compound(s) of component (1) and the
compound(s) of component (2) individually.
Preferred compositions for reasons of ease of synthesis or greater fungicidal
activity are:
Preferred 1. A fungicidal composition comprising a fungicidally effective amount
of (1) at least one quinazolinone of Formula I (including all geometric and
stereoisomers), iV-oxides, and agriculturally suitable salts thereof, wherein
R1 is C1-C6 alkyl;
R2 is C1-C6 alkyl;
R3 is halogen and fixed at position 6 of the quinazolinone; and
R4 is hydrogen or halogen and fixed at position 8 of the quinazolinone;
and (2) at least one compound selected from
(a) compounds of Formula II (including all geometric and stereoisomers),
N-oxides, and agriculturally suitable salts thereof,
wherein
E is selected from:
i) 1,2-phenylene optionally substituted with R13 or both R13 and
R14;
ii) a naphthalene ring, provided that when G and Y are attached to
the same ring, then G and Y are attached to adjacent ring members,
the naphthalene ring optionally substituted with R13 or both R13
and R14; and
iii) a ring system selected from 5 to 12-membered monocyclic and
fused bicyclic aromatic heterocyclic ring systems, each heterocyclic
ring system containing 1 to 6 heteroatoms independently selected
from the group nitrogen, oxygen, and sulfur, provided that each
heterocyclic ring system contains no more than 4 nitrogens, no
more than 2 oxygens, and no more than 2 sulfurs, each fused
bicyclic ring system optionally containing one nonaromatic ring
that optionally includes one or two J1 as ring members and
optionally includes one or two ring members independently
selected from C(=O) and S(O)2, provided that G is attached to an
aromatic ring, and when G and Y are attached to the same ring,
then G and Y are attached to adjacent ring members, each aromatic
heterocyclic ring system optionally substituted with R13 or both
R13 and R14;
A is O, S, N, NR15 or CR24;
G is C or N; provided that when G is C, then A is O, S or NR15 and the
floating double bond is attached to G; and when G is N, then A is N
or CR24 and the floating double bond is attached to A;
W is O, S, NH, N(C1-C6 alkyl) or NO(C1-C6 alkyl);
W1 is O or NH;
X is H, OR11, S(O)mR11, halogen, C1-C6 alkyl, C1-C6 haloalkyl,
C3-C6 cycloalkyl, cyano, NH2, NHR11, N(C1-C6 alkyl)R11,
NH(C1-C6 alkoxy) or N(C1-C6 alkoxy)R11;
X1 is CH or N;
R11 is C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl,
C2-C6 alkynyl, C2-C6 haloalkynyl, C3-C6 cycloalkyl,
C2-C4 alkylcarbonyl or C2-C4 alkoxycarbonyl;
R12 is H, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl,
C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl,
C3-C6 cycloalkyl, C2-C4 alkylcarbonyl, C2-C4 alkoxycarbonyl,
hydroxy, C1-C2 alkoxy or acetyloxy;
R13 and R14 are each independently halogen; cyano; nitro; hydroxy;
C1-C6 alkyl; C1-C6 haloalkyl; C2-C6 alkenyl; C2-C6 haloalkenyl;
C2-C6 alkynyl; C2-C6 haloalkynyl; CpC6 alkoxy;
C1-C6 haloalkoxy; C2-C6 alkenyloxy; C2-C6 alkynyloxy;
C1-C6 alkylthio; C1-C6 alkylsulfinyl; C1-C6 alkylsulfonyl; formyl;
C2-C6 alkylcarbonyl; C2-C6 alkoxycarbonyl; NH2C(O);
(C1-C4 alkyl)NHC(O); (C1-C4 alkyl)2NC(O); Si(R35)3; Ge(R35)3;
(R35)3Si-C=C-; or phenyl, phenylethynyl, benzoyl, or
phenylsulfonyl each substituted with R18 and optionally substituted
with one or rnc re R20; or
when E is 1,2-phenylene and R13 and R14 are attached to adjacent atoms,
R13 and R14 can be taken together as C3-C5 alkylene,
C3-C5 haloalkylene, C3-C5 alkenylene or C3-C5 haloalkenylene
each optionally substituted with 1-2 C1-C3 alkyl;
R15 is H, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl,
C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl,
C3-C6 cycloalkyl, C2-C4 alkylcarbonyl or C2-C4 alkoxycarbonyl;
Y is -0-, -S(O)n-, -NR25-, -C(=O)-, -CH(OR25)-, -CHR16-,
-CHR16CHR16, -CR16=CR16-, -C=C-, -CHR25O-, -OCHR25-,
-CHR25s(O)n-, -S(O)nCHR25-, -CHR25O-N=C(Rl7)-,
-(R17)C=N-OCH(R25)-, -C(R17)=N-O-, -O-N=C(Rl7)-,
-CHR25OC(=O)N(R25)-,-CHR25OC(=S)N(R25)-,
-CHR250C(=O)O-, -CHR25OC(=S)O-, -CHR25OC(=O)S-,
-CHR250C(=S)S-,-CHR25SC(=O)N(R25)-,
-CHR25SC(=S)N(R25)-, -CHR25SC(=O)O-, -CHR25SC(=S)O-,
-CHR25SC(=O)S-, -CHR25SC(=S)S-, -CHR25SC(=NR25)S-,
-CHR25N(R25)C(=O)N(R25)-, -CHR25O-N(R25)C(=O)N(R25)-,
-CHR25O-N(R25)C(=S)N(R25)-, -CHR25O-N=C(R17)NR25.,
-CHR25O-N=C(Rl7)OCH2-, -CHR25O-N=C(R17)-N=N-,
-CHR25O-N=C(R17)-C(=O)-,
-CHR25O-N=C(R17)-C(=N-A2-Z1)-Al-,
-CHR25O-N=C(R17)-C(R17)=N-A2-A3.,
-CHR25O-N=C(-C(R17)=N-A2-Z1)-,-CHR25O-N=C(R17)-CH2O-,
-CHR25O-N=C(R17)-CH2S-, -O-CH2CH2O-N=CCR17)-,
-CHR25O-C(R25)=C(R17)-, -CHR25O-CCR17)=N-,
-CHR25S-C(Rl7)=N-, -C(Rl7)=N-NR25., -CH=N-N=C(R17)-,
-CHR25N(R25)-N=C(R17)-, -CHR25N(COCH3)-N=C(R17)-,
-OC(=S)NR25C(=O)-,-CHRl6-C(=W2)-A1-,
-CHR16CHR16-C(=W2)-A1-,-CR16=CR16-C(=W2)-A1-,
-C=C-C(=W2)-A1-, -N=CR16-C(=W2)-A1- or a direct bond; and
the directionality of the Y linkage is defined such that the moiety
depicted on the left side of the linkage is bonded to E and the
moiety on the right side of the linkage is bonded to Z;
Z1 is H or-A3-Z;
W2 is O or S;
A1 is O, S, NR25 or a direct bond;
A2 is O, NR25 or a direct bond;
A3 is -C(=O)-, -S(O)2- or a direst bond;
each R16 is independently H, 1-2 CH3, C2-C3 alkyl, C1-C3 alkoxy,
C3-C6 cycloalkyl, formylamino, C2-C4 alkylcarbonylamino,
C2-C4 alkoxycarbonylamino, NH2C(O)NH,
(C1-C3 alkyl)NHC(O)NH, (C1-C3 alkyl)2NC(O)NH,
N(C1-C3 alkyl)2, piperidinyl, morpholinyl, 1-2 halogen, cyano or
nitro;
each R17 is independently H, C1-C6 alkyl, C1-C6 haloalkyl,
C1-C6 alkoxy, C1-C5 haloalkoxy, C1-C6 alkylthio,
C1-C6 alkylsulfmyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylthio,
C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl, C2-C6 alkenyl,
C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl,
C3-C6 cycloalkyl, C2-C4 alkylcarbonyl, C2-C4 alkoxycarbonyl,
halogen, cyano, nitro, hydroxy, amino, NH(C1-C6 alkyl),
N(C1-C6 alkyl)2 or morpholinyl;
each Z is independently selected from:
i) C1-C10 alkyl, C2-C10 alkenyl and C2-C10 alkynyl each
substituted with R19 and optionally substituted with one or more
R20;
ii) C3-C8 cycloalkyl, C3-C8 cycloalkenyl and phenyl each
substituted with R19 and optionally substituted with one or more
R20;
iii) a ring system selected from 3 to 14-membered monocyclic,
fused bicyclic and fused tricyclic nonaromatic heterocyclic ring
systems and 5 to 14-membered monocyclic, fused bicyclic and
fused tricyclic aromatic heterocyclic ring systems, each
heterocyclic ring system containing 1 to 6 heteroatoms
independently selected from the group nitrogen, oxygen, and sulfur,
provided that each heterocyclic ring system contains no more than
4 nitrogens, no more than 2 oxygens, and no more than 2 sulfurs,
each nonaromatic or aromatic heterocyclic ring system substituted
with R19 and optionally substituted with one or more R20;
iv) a multicyclic ring system selected from 8 to 14-membered
fused-bicyclic and fused-tricyclic ring systems which are an
aromatic carbocyclic ring system, a nonaromatic carbocyclic ring
system, or a ring system containing one or two nonaromatic rings
that each include one or two J1 as ring members and one or two
ring members independently selected from C(=O) and S(O)2, and
any remaining rings as aromatic carbc cyclic rings, each multicyclic
ring system substituted with R19 and optionally substituted with
one or more R20; and
v) adamantyl substituted with R19 and optionally substituted with
one or more R20;
each J1 is independently selected from the group -CHR23-, -NR23-, -O-
and -S(O)p-;
R18 is H, 1-2 halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy,
C1-C6 haloalkoxy, C2-C6 alkenyl, C2-C6 haloalkenyl,
C2-C6 alkynyl, C1-C6 alkylthio, C1-C6 haloalkylthio,
C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C3-C6 cycloalkyl,
C3-C6 alkenyloxy, CO2(C1-C6 alkyl), NH(C1-C6 alkyl),
N(C1-C6 alkyl)2, cyano, nitro, SiR29R30R31 or GeR29R30R3l;
R19 is H; 1-2 halogen; C1-C6 alkyl; C1-C6 haloalkyl; C1-C6 alkoxy;
C1-C6 haloalkoxy; C2-C6 alkenyl; C2-C6 halpalkenyl;
C2-C6 alkynyl; C1-C6 alkylthio; C1-C6 haloalkylthio;
C1-C6 alkylsulfinyl; C1-C6 alkylsulfonyl; C3-C6 cycloalkyl;
C3-C6 alkenyloxy; CO2(C1-C6 alkyl); NH(C1-C6 alkyl);
N(C1-C6 alkyl)2; -C(R28)=NOR27; cyano; nitro; SF5;
SiR32R33R34; or GeR32R33R34; or R19 is phenyl, benzyl, benzoyl,
phenoxy, pyridinyl, pyridinyloxy, thienyl, thienyloxy, furanyl,
pyrimidinyl or pyrimidinyloxy each optionally substituted with R21
or both R21 and R22;
each R20 is independently halogen, C1-C4 alkyl, C1-C4 haloalkyl,
C1-C4 alkoxy, nitro or cyano; or
when R19 and an R20 are attached to adjacent atoms on Z, R19 and said
adjacently attached R20 can be taken together as -OCH2O- or
-OCH2CH2O-; each CH2 group of said taken together R19 and R20
optionally substituted with 1-2 halogen; or
when Y and an R20 are attached to adjacent atoms on Z and Y is
-CHR25O-N=C(R17)-, -O-N=C(R17)-, -O-CH2CH2O-N=C(R17)-,
-CHR25O-C(R25)=C(R17)-,-CH=N-N=C(R17)-,
-CHR25N(R25)-N=C(R17)- or -CHR25N(COCH3)-N=C(R17)-, R17
and said adjacently attached R20 can be taken together as
-(CH2)r-J- such that J is attached to Z;
J is -CH2-, -CH2CH2-, -OCH2-, -CH2O-, -SCH2-, -CH2S-, -N(R26)CH2-
or -CH2N(R26)-; each CH2 group of said J optionally substituted
with 1 to 2 CH3;
R21 and R22 are each independently 1-2 halogen; C1-C4 alkyl;
C1-C4 haloalkyl; C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C6
alkynyl; C2-C6 haloalkynyl; C2-C6 alkoxyalkyl; C2-C6
alkylthioalkyl; C3-C6 alkoxyalkynyl;
C7-C10 tetrahydropyranyloxyalkynyl; benzyloxymethyl; C1-C4
alkoxy; C1-C4 haloalkoxy; C3-C6 alkenyloxy; C3-C6
haloalkenyloxy; C3-C6 alkynyloxy; C3-C6 haloalkynyloxy; C2-C6
alkoxyalkoxy; C5-C9 trialkylsilylalkoxyalkoxy;
C2-C6 alkylthioalkoxy; C1-C4 alkylthio; C1-C4 haloalkylthio;
C1-C4 alkylsulfinyl; C1-C4 haloalkylsulfinyl; C1-C4 alkylsulfonyl;
C1-C4 haloalkylsulfonyl; C3-C6 alkenylthio;
C3-C6 haloalkenylthio; C2-C6 alkylthioalkylthio; nitro; cyano;
thiocyanato; hydroxy; N(R36)2; SF5; Si(R35)3; Ge(R35)3;
(R35)3Si-C=C-; OSi(R35)3; OGe(R35)3; C(=O)R36; C(=S)R36;
C(=O)OR36; C(=S)OR36; C(=O)SR36; C(=S)SR36; C(=O)N(R36)2;
C(=S)N(R36)2; OC(=O)R36; OC(=S)R36; SC(=O)R36; SC(=S)R36;
N(R36)C(=O)R36; N(R36)C(=S)R36; OC(=O)OR37; OC(=O)SR37;
OC(=O)N(R36)2; SC(=O)OR37; SC(=O)SR37; S(O)2OR36;
S(O)2N(R36)2; OS(O)2R37; N(R36)S(O)2R37; or phenyl, phenoxy,
benzyl, benzyloxy, phenylsulfonyl, phenylethynyl or
pyridinylethynyl, each optionally substituted with halogen,
C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy,
nitro or cyano;
each R23 is independently H; C1-C6 alkyl; C1-C6 haloalkyl; or phenyl
optionally substituted with halogen, C1-C4 alkyl, C1-C4 haloalkyl,
C1-C4 alkoxy, C1-C4 haloalkoxy, nitro or cyano;
R24 is H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl,
C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl or
C3-C6 cycloalkyl;
each R25 is independently H; C1-C3 alkyl; C3-C6 cycloalkyl; or phenyl or
benzyl, each optionally substituted on the phenyl ring with halogen,
C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy,
nitro or cyano; or
when Y is -CHR25N(R25)C(=O)N(R25)-, the two R25 attached to
nitrogen atoms on said group can be taken together as -(CH2)S-; or
when Y is -CHR25O-N=C(R17)NR25-, R17 and the adjacently attached
R25 can be taken together as -CH2-(CH2)S-, -O-(CH2)s-,
-S-(CH2)S- or -N(C1-C3 alkyl)-(CH2)s-; with the directionality of
said linkage defined such that the moiety depicted on the left side
of the linkage is bonded to the carbon and the moiety on the right
side of the linkage is bonded to the nitrogen;
R26, R27 and R28 are each independently H; C1-C3 alkyl;
C3-C6 cycloalkyl; or phenyl optionally substituted with halogen,
C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy,
nitro or cyano;
R29, R30, R3l, R32, R33 and R34 are each independently C1-C6 alkyl,
C2-C6 alkenyl, C1-C4 alkoxy or phenyl;
each R35 is independently C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl,
C1-C4 alkoxy or phenyl;
each R36 is independently H; C1-C6 alkyl; C1-C6 haloalkyl;
C2-C6 alkenyl; C2-C6 haloalkenyl; C2-C6 alkynyl;
C2-C6 haloalkynyl; C3-C6 cycloalkyl; or phenyl or benzyl, each
optionally substituted on the phenyl ring with halogen, C1-C4 alkyl,
C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, nitro or cyano;
each R37 is independently C1-C6 alkyl; C1-C6 haloalkyl; C2-C6 alkenyl;
C2-C6 haloalkenyl; C2-C6 alkynyl; C2-C6 haloalkynyl;
C3-C6 cycloalkyl; or phenyl or benzyl, each optionally substituted
on the phenyl ring with halogen, C1-C4 alkyl, C1-C4 haloalkyl,
C1-C4 alkoxy, C1-C4 haloalkoxy, nitro or cyano;
m, n and p are each independently 0,1 or 2;
r is 0 or 1; and
s is 2 or 3;
and (b) bromuconazole, cyproconazole, difenoconazole, diniconazole,
epoxiconazole, fenarimol, fenbuconazole, fenpropidin,
fenpropimorph, fluquinconazole, flusilazole, flutriafol,
hexaconazole, ipconazole, metconazole, penconazole,
propiconazole, tebuconazole, tetraconazole, triadimefon,
triadimenol, tridemorph, triticonazole and uniconazole.
Preferred 2. The fungicidal composition of Preferred 1 comprising a fungicidally
effective amount of (1) at least one compound selected from the group
consisting of
6-bromo-3-propyl-2-propyloxy-4(3H)-quinazolinone,
6,8-diiodo-3-propyl-2-propyloxy-4(3H)-quinazolinone and
6-iodo-3-propyl-2-propyloxy-4(3H)-quinazolinone;
and (2) at least one compound selected from the group consisting of
2,4-dihydro-5-methoxy-2-methyl-4-[2-[[[[1-[3-
(trifluoromethyl)phenyl]ethylidene]amino]oxy]methyl]
phenyl]-3H-1,2,4-triazol-3-one, kresoxim-methyl,
azoxystrobin, (E)-2-(methoxyimino)-N-methyl-2-(2-
phenoxyphenyl)acetamide, flusilazole, epoxiconazole,
fenpropimorph, propiconazole and tebuconazole.
Preferred 3. The fungicidal composition of Preferred 2 comprising a fungicidally
effective amount of (1) 6-iodo-3-propyl-2-propyloxy-4(3H)-quinazolinone
(sometimes referred to hereafter as the Formula 1a compound) and (2) 2,4-
dihydro-5-methoxy-2-methyl-4-[2-[[[[1-[3-
(trifluoromethyl)phenyl]ethylidene]amino]oxy]methyl]phenyl]-3H-1,2,4-
triazol-3-one (sometimes referred to hereafter as the Formula Ha
compound).
Preferred 4. The fungicidal composition of Preferred 2 comprising a fungicidally
effective amount of (1) 6-iodo-3-propyl-2-propyloxy-4(3H)-quinazolinone
and (2) flusilazole.
Preferred 5. The fungicidal composition of Preferred 2 comprising a fungicidally
effective amount of (1) 6-iodo-3-propyl-2-propyloxy-4(3H)-quinazolinone
and (2) tebuconazole.
Preferred 6. The fungicidal composition of Preferred 2 comprising a fungicidally
effective amount of (1) 6-iodo-3-propyl-2-propyloxy-4(3H)-quinazolinone,
and (2) both 2,4-dihydro-5-methoxy-2-methyl-4-[2-[[[[1-[3-
(trifluoromethyl)phenyl]ethylidene]amino]oxy]methyl]phenyl]-3H-1,2,4-
triazol-3-one and flusilazole.
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, hexyl, heptyl, octyl,
nonyl and decyl isomers. The term "1-2 CH3" indicates that the substituent can be
methyl (i.e., Me) or, when there is a hydrogen attached to the same atom, the substituent
and said hydrogen can both be methyl. "Alkenyl" includes straight-chain or branched
alkenes such as ethenyl, 1 -propenyl, 2-propenyl, and the different butenyl, pentenyl,
hexenyl, heptenyl, octenyl, nonenyl and decenyl 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, hexynyl, heptynyl, octynyl, nonynyl, and decynyl isomers. "Alkynyl" can
also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl.
"Alkylene" denotes a straight-chain or branched alkanediyl. Examples of
"alkylene" include CH2CH2CH2, CH2CH(CH3) and the different butylene and
pentylene isomers. "Haloalkylene" denotes a halogen substituted alkylene. Examples
of "haloalkylene" include CH2CH(CF3), CH2CF2CH2 and CH2CH(CCl3).
"Alkenylene" denotes a straight-chain or branched alkenediyl containing one olefinic
bond. Examples of "alkenylene" include CH2CH=CH and CH=C(CH3) and the
different butenylene and pentenylene isomers. "Haloalkenylene" denotes a halogen
substituted alkenylene. Examples of "haloalkenylene" include CH2CCl=CCl and
CH=C(CF3).
"Alkenyloxyalkyl" denotes alkenyl substitution on oxygen which in turn is
substituted on alkyl. Examples "alkenyloxyalkyl" include CH2=CHCH2OCH2 and
CH3CH=CHCH2OCH2CH2. "Alkynyloxyalkyl" denotes alkynyl substitution on
oxygen which in turn is substituted on alkyl. Examples of "alkynyloXyalkyl" include
CH=CCH2OCH2 and CH3C=CCH2OCH2CH2.
"Alkoxy" includes, for example, methoxy, ethoxy, propyloxy, 1-methylethoxy
and the different butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, and
decyloxy isomers. "Alkoxyalkyl" denotes alkoxy substitution on alkyl. Examples of
"alkoxyalkyl" include CH3OCH2, CH3OCH2CH2, CH3CH2OCH2,
CH3CH2CH2CH2OCH2 and CH3CH2OCH2CH2. "Alkoxyalkoxy" denotes alkoxy
substitution on alkoxy. Examples of "alkoxyalkoxy" include CH3OCH2O,
(CH3)3COCH2O and CH3OCH2CH2O. "Alkenyloxy" includes straight-chain or
branched alkenyloxy moieties. Examples of "alkenyloxy" include H2C=CHCH2O,
(CH3)2C=CHCH2O, (CH3)CH=CHCH2O, (CH3)CH=C(CH3)CH2O and
CH2=CHCH2CH2O. "Alkynyloxy" includes straight-chain or branched alkynyloxy
moieties. Examples of "alkynyloxy" include HC=CCH2O, CH3OCCH2O and
CH3OCCH2CH2O. "Alkoxyalkenyl" denotes alkoxy substitution of alkenyl.
"Alkoxyalkenyl" includes straight-chain or branched alkoxyalkenyl moieties. Examples
of "alkoxyalkenyl" include (CH3)2CHOCH=CH and CH3OCH2CH=CH.
"Alkoxyalkynyl" denotes alkoxy substitution of alkynyl. "Alkoxyalkynyl" includes
straight-chain or branched alkoxyalkynyl moieties. Examples of "alkoxyalkynyl"
include (CH3)2CHOCH2C=C and CH3OCH2C=C.
"Alkylthio" includes branched or straight-chain alkylthio moieties such as
methylthio, ethylthio, and the different propylthio, butylthio, pentylthio, hexylthio,
heptylthio, octylthio, nonylthio and decylthio isomers. "Alkylthioalkyl" denotes
alkylthio substitution on alkyl. Examples of "alkylthioalkyl" include CH3SCH2,
CH3SCH2CH2, CH3CH2SCH2, CH3CH2CH2CH2SCH2 and CH3CH2SCH2CH2.
"Alkylthioalkoxy" denotes alkylthio substitution on alkoxy. Examples of
"alkylthioalkoxy" include CH3SCH2O and CH3CH2SCH2CH2O. "Alkylthioalkylthio"
denotes alkylthio substitution on alkylthio. Examples of "alkylthioalkylthio" include
CH3SCH2S and CH3SCH2CH2S. "Alkylsulfinyl" includes both enantiomers of an
alkylsulfinyl group. Examples of "alkylsulfinyl" include CH3S(O), CH3CH2S(O),
CH3CH2CH2S(O), (CH3)2CHS(O) and the different butylsulfinyl, pentylsulfinyl,
hexylsulfinyl, heptylsulfinyl and octylsulfinyl isomers. "Alkylsulfinylalkyl" denotes
alkylsulfinyl substitution on alkyl. Examples of "alkylsulfinylalkyl" include
CH3S(O)CH2, CH3S(O)CH2CH2, CH3CH2S(O)CH2, CH3CH2CH2CH2S(O)CH2 and
CH3CH2S(O)CH2CH2. Examples of "alkylsulfonyl" includeCH3S(O)2,
CH3CH2S(O)2, CH3CH2CH2S(O)2, (CH3)2CHS(O)2 and the different butylsulfonyl,
pentylsulfonyl, hexylsulfonyl, heptylsulfonyl and octylsulfonyl isomers.
"Alkylsulfonylalkyl" denotes alkylsulfonyl substitution on alkyl. Examples of
"alkylsulfonylalkyl" include CH3S(O)2CH2, CH3S(O)2CH2CH2, CH3CH2S(O)2CH2,
CH3CH2CH2CH2S(O)2CH2 and CH3CH2S(O)2CH2CH2. "Alkylthioalkenyl" denotes
alkylthio substitution on alkenyl. Examples of "alkylthioalkenyl" include
CH3SCH2CH=CH and CH3CH2SCH=CH. "Alkylthioalkynyl" denotes alkylthio
substitution on alkynyl. Examples of "alkylthioalkynyl" include CH3SCH2C=C and
CH3CH2SCH2CH2C=C. "Alkenylthio" includes straight-chain and branched
alkenylthio moieties. Examples of "alkenylthio" include CH2=CHCH2S and
CH2=CHCH2CH2S. "Alkenylthioalkyl" denotes alkenylthio substitution on alkyl.
Examples of "alkenylthioalkyl" include CH2=CHCH2SCH2 and
CH2=CHCH2CH2SCH2. "Alkynylthio" includes straight-chain and branched
alkynylthio moieties. Examples of "alkynylthio" include CH=CCH2S and
CH=CCH2CH2S. "Alkynylthioalkyl" denotes alkynylthio substitution on alkyl.
Examples of "alkynylthioalkyl" include CH=CCH2SCH2 and CH=CCH2CH2SCH2.
"Cycloalkyl" includes, for example, cyclopropyl, cyclobutyl, cyclopentyl,
cyclohexyl, cycloheptyl and cyclooctyl. "(Cycloalkyl)oxyalkyl" denotes cycloalkyl
substituted on oxygen which in turn is substituted on alkyl. Examples of
"(cycloalkyl)oxyalkyl" include (cyclopentyloxy)methyl and (cyclohexyloxy)methyl.
"(Cycloalkyl)thioalkyl" denotes cycloalkyl substituted on sulfur which in turn is
substituted on alkyl. Examples of "(cycloalkyl)thioalkyl" include
(cyclopentylthio)methyl and (cyclohexylthio)methyl. "Cycloalkenyl" includes groups
such as cyclopentenyl and cyclohexenyl as well as groups with more than one double
bond such as 1,3- and 1,4-cyclohexadienyl. Examples of "cycloalkylalkyl" include
cyclopropylmethyl, cyclopentylethyl, and other cycloalkyl moieties bonded to
straight-chain or branched alkyl groups.
"Cyanoalkyl" denotes an alkyl group substituted with one cyano group. Examples
of "cyanoalkyl" include NCCH2, NCCH2CH2 and CH3CH(CN)CH2. "Nitroalkyl"
denotes an alkyl group substituted with one nitro group. Examples of "nitroalkyl"
include NO2CH2 and CH3CH(NO2)CH2.
"Tetrahydropyranyloxyalkynyl" denotes a tetrahydropyranyl group on oxygen
which in turn is substituted on an alkynyl group. An example of
"tetrahydropyranyloxyalkynyl" is 2-[(tetrahydro-2H-pyranyl)oxy]ethynyl.
The term "aromatic ring system" denotes fully unsaturated carbocycles and
heterocycles in which the polycyclic ring system is aromatic (where aromatic indicates
that the Huckel rule is satisfied for the ring system). The term "aromatic carbocyclic
ring system" includes fully aromatic carbocycles and carbocycles in which at least one
ring of a polycyclic ring system is aromatic (where aromatic indicates that the Huckel
rule is satisfied). The term "nonaromatic carbocyclic ring system" denotes fully
saturated carbocycles as well as partially or fully unsaturated carbocycles where the
Huckel rule is not satisfied by any of the rings in the ring system. 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 Huckel rule is satisfied). Examples of "aromatic heterocyclic ring systems"
include furanyl, furazanyl, thienyl, pyrrolyl, pyrazolyl, oxazolyl, oxadiazolyl,
imidazolyl, isoxazolyl, thiazolyl, thiadiazolyl, isothiazolyl, pyridyl, pyrimidinyl,
pyridazinyl, pyrazinyl and triazinyl with said ring attached through any available carbon
or nitrogen. For example, when the aromatic heterocyclic ring is furanyl, it can be
2-furanyl or 3-furanyl, for pyrrolyl, the aromatic heterocyclic ring is 1-pyrrolyl,
2-pyrrolyl or 3-pyrrolyl, for pyridyl, the aromatic ring is 2-pyridyl, 3-pyridyI or
4-pyridyl and similarly for other aromatic heterocyclic rings. The term "nonaromatic
heterocyclic ring system" denotes fully saturated heterocycles as well as partially or
fully unsaturated heterocycles where the Hilckel rule is not satisfied by any of the rings
in the ring system. The heterocyclic ring systems can be attached through any available
carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.
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 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 N-oxides. Synthetic methods for the preparation of N-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 hydroperoxides 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
Synthesis, vol. 7, pp 748-750, S. V. Ley, Ed., Pergamon Press; M. Tisler and
B. Stanovnik in Comprehensive Heterocyclic 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 Heterocyclic Chemistry, vol. 43, pp 149-161, 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. Werstiuk in Advances in Heterocyclic Chemistry, vol.
22, pp 390-392, A. R. Katritzky and A. J. Boulton, Eds., Academic Press.
The term "halogen", either alone or in compound words such as "haloalkyl",
includes fluorine, chlorine, bromine or iodine. The term "1-2 halogen" indicates that
one or two of the available positions for that substituent may be halogen which are
independently selected. 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, ClCH2, CF3CH2 and
CF3CCl2. The terms "haloalkenyl", "haloalkenyloxy", "haloalkenylthio",
"haloalkenyloxyalkyl", "haloalkynyl", "haloalkynyloxy", "haloalkynyloxyalkyl",
"haloalkoxy", "haloalkoxyalkyl", "haloalkylthio", "haloalkylsulfinyl",
"haloalkylsulfonyl", and the like, are defined analogously to the term "haloalkyl".
Examples of "haloalkenyl" include (Cl)2C=CHCH2 and CF3CH2CH=CHCH2.
Examples of "haloalkenyloxy" include (Cl)2C=CHCH2O and CF3CH2CH=CHCH2O.
Examples of "haloalkenylthio" include (Cl)2OCHCH2S and CF3CH2CH=CHCH2S.
Examples of "haloalkenyloxyalkyl" include (Cl)2C=CHCH2OCH2 and
CF3CH2CH=CHCH2OCH2. Examples of "haloalkynyl" include HC=CCHCl, CF3OC,
CCl3OC and FCH2OCCH2. Examples of "haloalkynyloxy" include CF3C=CCH2O,
CCl3C=CCH2O and FCH2C=CCH2O. Examples of "haloalkynyloxyalkyl" include
CCl3C=CCH2OCH2 and FCH2OCCH2CH2OCH2. Examples of "haloalkoxy" include
CF3O, CCl3CH2O, HCF2CH2CH2O and CF3CH2O. Examples of "haloalkoxyalkyl"
include CF3OCH2, CCl3CH2OCH2CH2, HCF2 CH2CH2OCH2 and CF3 CH2OCH2.
Examples of "haloalkylthio" include CCl3S, CF3S, CCl3CH2S and C1CH2CH2CH2S.
Examples of "haloalkylsulfinyl" include CF3S(O), CCl3S(O), CF3CH2S(O) and
CF3CF2S(O). Examples of "haloalkylsulfonyl" include CF3S(O)2, CCl3S(O)2,
CF3CH2S(O)2 and CF3CF2S(O)2.
"Alkylcarbonyl" denotes alkyl substituted carbonyl. Examples of "alkylcarbonyl"
include CH3C(=O) and (CH3)2CHC(=O). "Alkoxycarbonyl denotes alkoxy substituted
carbonyl. Examples of "alkoxycarbonyl" include CH3OC(=O) and (CH3)2CHOC(=O).
"Alkylcarbonylamino" denotes alkylcarbonyl substituted on nitrogen. Examples of
"alkylcarbonylamino" include CH3C(=O)NH and CH3CH2C(=O)NH.
"Alkoxycarbonylamino" denotes alkoxycarbonyl substituted on nitrogen. Examples of
"alkoxycarbonylamino" include CH3OC(=O)NH and CH3CH2OC(=O)NH.
Examples of "trialkylsilyl" include (CH3)3Si and (CH3)3CSi(CH3)2.
"Trialkylsilylalkyl" denotes trialkylsilyl substitution on alkyl. Examples of
"trialkylsilylalkyl" include (CH3)3SiCH2, and (CH3)3SiCH2CH2.
"Trialkylsilylalkynyl" denotes trialkylsilyl substitution on alkynyl. Examples of
"trialkylsilylalkynyl" include (CH3)3SiC=C and (CH3CH2)SiCH2C=C.
"Trialkylsilylalkoxyalkoxy" denotes trialkylsilyl substitution on alkoxy substituted in
turn on alkoxy. Examples of "trialkylsilylalkoxyalkoxy" include (CH3)3SiCH2OCH2O
and (CH3)3SiCH2CH2OCH2O.
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 11. 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(O)CH3, C(O)CH2CH2CH3 and C(O)CH(CH3)2. Examples
of "alkoxycarbonyl" include CH3OC(=O), CH3CH2OC(=O), CH3CH2CH2OC(=O),
(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 that
indicates the number of said substituents can exceed 1, said substituents (when they
exceed 1) are independently selected from the group of defined substituents. Further,
when the subscript indicates a range, e.g., (R)i_j, then the number of substituents may be
selected from the integers between i and j inclusive.
When a group contains a substituent which can be hydrogen, for example R4,
then, when this substituent is taken as hydrogen, it is recognized that this is equivalent
to said group being unsubstituted. When a group is optionally substituted with a
substituent, for example with R7, then, when the group is not substituted with that
substituent, it is recognized that this is equivalent to said group having a hydrogen
substituent.
Compounds used in this invention often 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). (See, e.g., U.S.
Provisional Patent Application Serial No. 60/057917 filed September 4, 1997, which is
hereby incorporated by reference in its entirety.) 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 salts of the compounds which may used in 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 salts of the compounds which
may be used in the invention also include those formed with organic bases (e.g.,
pyridine, ammonia, or triethylamine) or inorganic bases (e.g., hydrides, hydroxides, or
carbonates of sodium, potassium, lithium, calcium, magnesium or barium) when the
compound contains an acidic group such as a carboxylic acid or phenol.
The fungicidal compositions of this invention, in addition to comprising
fungicidally effective amounts of the mixtures of the invention, also optionally comprise
at least one of a surfactant, a solid diluent or a liquid diluent. The preferred
compositions of the present invention are those which comprise the above preferred
component (1) and component (2) compounds.
This invention also relates to a method for controlling plant diseases caused by
fungal plant pathogens comprising applying to the plant or portion thereof, or to the
plant seed or seedling, a fungicidally effective amount of the compositions of the
invention (e.g., as a composition described herein). The preferred methods of use
include those involving the above preferred compositions.
The bc1 Complex Fungicides
Compounds of Formula II are known to have a fungicidal mode of action which
inhibits the bc1 complex. Methyl (E)-2-[[6-(2-cyanophenoxy)-4-pyrirnidinyl]oxy]-a-
(methoxyimino)benzeneacetate is described as a bc1 complex inhibitor in Biochemical
Society Transactions 1993, 22, 68 S. Methyl (E)-a-(methoxyimino)-2-[(2-
methylphenoxy)methyl]benzeneacetate is described as a bc1 complex inhibitor in
Biochemical Society Transactions 1993,22, 64S. (E)-2-[(2,5-
Dimethylphenoxy)methyl] -a-(memoxyimino)-N-methylbenzeneacetamide is described
as a bc1 complex inhibitor in Biochemistry and Cell Biology 1995, 85(3), 306-311.
The bc1 complex is sometimes referred to by other names in the biochemical
literature, including complex III of the electron transfer chain, and
ubihydroquinonexytochrome c oxidoreductase. It is uniquely identified by the Enzyme
Commission number EC 1.10.2.2. The bc1 complex is described in, for example, J. Biol.
Chem. 1989, 264, 14543-38; Methods Enzymol. 1986, 126, 253-71; and references cited
therein.
The Sterol Biosynthesis Inhibitor Fungicides
The class of sterol biosynthesis inhibiton; includes DMI and non-DMI
compounds, that control fungi by inhibiting enzymes in the sterol biosynthesis pathway.
DMI fungicides have a common site of action within the fungal sterol biosynthesis
pathway; that is, an inhibition of demethylation at position 14 of lanosterol or 24-
methylene dihydrolanosterol, which are precursors to sterols in fungi." Compounds
acting at this site are often reffered to as demethylase inhibitors, DMI fungicides, or
DMIs. The demethylase enzyme is sometimes referred to by other names in the
biochemical literature, including cytochrome P-450 (14DM). The demethylase enzyme
is described in, for example, J. Biol. Chem. 1992, 267, 13175-79 and references cited
therein. DMI fungicides fall into several classes: triazoles, imidazoles, pyrimidines,
piperazines and pyridines. The triazoles includes bromuconazole, cyproconazole,
difenoconazole, diniconazole, epoxiconazole, fenbuconazole, fluquinconazole,
flusilazole, flutriafol, hexaconazole, ipconazole, metconazole, penconazole,
propiconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole and
uniconazole. The imidazoles include clotrimazole, econazole, imazalil, isoconazole,
miconazole and prochloraz. The pyrimidines include fenarimol, nuarimol and triarimol.
The piperazines include triforine. The pyridines include buthiobate and pyrifenox.
Biochemical investigations have shown that all of the above mentioned fungicides are
DMI fungicides as described by K. H. Kuck, et al. in Modern Selective Fungicides -
Properties, Applications and Mechanisms of Action, Lyr, H., Ed.; Gustav Fischer
Verlag: New York, 1995, 205-258.
The DMI fungicides have been grouped together to distinguish them from other
sterol biosynthesis inhibitors, such as, the morpholine and piperidine fungicides. The
morpholines and piperidines are also sterol biosynthesis inhibitors but have been shown
to inhibit later steps in the sterol biosynthesis pathway. The morpholines include
aldimorph, dodemorph, fenpropimorph, tridemorph and trimorphamide. The
piperidines include fenpropidin. Biochemical investigations have shown that all of the
above mentioned morpholine and piperidine fungicides are sterol biosynthesis inhibitor
fungicides as described by K. H. Kuck, et al. in Modern Selective Fungicides -
Properties, Applications and Mechanisms of Action, Lyr, H., Ed.; Gustav Fischer
Verlag: New York, 1995, 185-204.
Synergistic Effects
Fungicides that effectively control plant fungi, particularly wheat powdery mildew
(Erysiphe graminis) and wheat foot rot (Pseudocercosporella herpotrichoides), are in
constant demand by growers. Combinations of fungicides are often used to facilitate
disease control and to retard resistance development. Mixtures of fungicides may
provide significantly better disease control than could be predicted based on the activity
of the individual components. This synergism has been described as "the cooperative
action of two components of a mixture, such that the total effect is greater or more
prolonged than the sum of the effects of the two (or more) taken independently" (see
Tames, P. M. L., Neth. J. Plant Pathology, (1964), 70, 73-80). It has been demonstrated
that compositions containing compounds of Formula Ia and Formula IIa; Formula Ia
and flusilazole; Formula Ia and tebuconazole; and Formula Ia, Formula IIa and
flusilazole exhibit synergistic effects.
The presence of a synergistic effect between two active ingredients is established
with the aid of the Colby equation (see Colby, S. R. In Calculating Synergistic and
Antagonistic Responses of Herbicide Combinations, Weeds, (1967), 15, 20-22):

Using the methods of the Colby, the presence of a synergistic interaction between
two active ingredients is established by first calculating the predicted activity, p, of the
mixture based on activities of the two components applied alone. If p is lower than the
experimentally established effect, synergism has occurred. In the equation above, A is
the fungicidal activity in percentage control of one component applied alone at rate x.
The B term is the fungicidal activity in percentage control of the second component
applied at rate y. The equation estimates p, the fungicidal activity of the mixture of A at
rate x with B at rate y if their effects are strictly additive and no interaction has
occurred.
The Colby equation for a three way mixture is

In this application, fungicidal activities provided by compositions of Formula a,
Formula Ia, flusilazole and tebuconazole alone are compared with that of compositions
of the compounds of Formula Ia and Formula IIa together, compositions of the
compounds of Formula Ia and flusilazole together, compositions of the compounds of
Formula Ia and tebuconazole together, and compositions of the compounds of
Formula Ia, Formula IIa and flusilazole together. Based on the description of synergism
developed by Colby, compositions of the present invention are considered to be
synergistically useful. Accordingly, this invention provides an improved method of
combating fungi, such as wheat powdery mildew (Erysiphe graminis), wheat leaf rust
{Puccinia recondita), wheat foot rot (Pseudocercosporella herpotrichoides) and/or
wheat glume blotch (Septoria nodorum) in crops, especially cereals.
Compositions are provided in accordance with this invention which comprise
proportions of component (1) and component (2) which are especially useful for
controlling particular fungal diseases. For example, the compositions of this invention
include those wherein the mole ratio of component (1) to component (2) is from about
30:1 to 1:30. These compositions are considered especially useful for controlling wheat
powdery mildew (Erysiphe graminis), wheat leaf rust {Puccinia recondita), wheat foot
rot (Pseudocercosporella herpotrichoides) and/or wheat glume blotch (Septoria
nodorum). Preferred component (1) compounds for these compositions include
6-bromo-3-propyl-2-propyloxy-4(3H)-quinazolinone;
6,8-diiodo-3-propyl-2-propyloxy-4(3H)-quinazolinone;and
6-iodo-3-propyl-2-propyloxy-4(3H)-quinazolinone; with
6-iodo-3-propyl-2-propyloxy-4(3H)-quinazolinone being particularly preferred.
Preferred component (2) compounds for these compositions include 2,4-dihydro-5-
methoxy-2-methyl-4-[2-[[[[1-[3-
(trifluoromethyI)phenyl]ethylidene]amino]oxy]methyl]phenyl]-3H-1,2,4-triazol-3-one,
kresoxim-methyl, azoxystrobin, (E)-2-(methoxyimino)-N-methyl-2-(2-
phenoxyphenyl)acetamide, fiusilazole, epoxiconazole, fenpropimorph, propiconazole
and tebuconazole; with 2,4-dihydro-5-methoxy-2-methyl-4-[2-[[[[1-[3-
(trifiuoromethyl)phenyl]ethylidene]amino]oxy]methyl]phenyl]-3H-1,2,4-triazol-3-one,
fenpropimorph, fiusilazole, epoxiconazole and propiconazole being particularly
preferred. Preferably, the mole ratio of component (1) to component (2) for these
compositions is from about 4:1 to 1:4. Example compositions of this type include
compositions comprising 6-iodo-3-propyl-2-propyloxy-4(3H)-quinazolinone and 2,4-
dihydro-5-methoxy-2-methyl-4-[2-[[[[ 1-[3-
(trifluoromemyl)phenyl]emylidene]amino]oxy]methyl]phenyl]-3H-1,2,4-triazol-3-one
in a mole ratio of the compound of Formula Ia to the compound of Formula IIa of from
about 4:1 to 1:4, compositions comprising
6-iodo-3-propyl-2-propyloxy-4(3H)-quinazolinone and fenpropimorph in a mole ratio of
the compound of Formula Ia to fenpropimorph of from about 1:1 to 1:10, compositions
comprising 6-iodo-3-propyl-2-propyloxy-4(3H)-quinazolinone and fiusilazole in a mole
ratio of the compound of Formula Ia to fiusilazole of from about 15:1 to 1:15,
compositions comprising 6-iodo-3-propyl-2-propyloxy-4(3H)-quinazolinone and
tebuconazole in a mole ratio of the compound of Formula Ia to tebuconazole of from
about 30:1 to 1:30, and compositions comprising
6-iodo-3-propyl-2-propyloxy-4(3H)-quinazolinone;2,4-dihydro-5-methoxy-2-methyl-4-
[2-[[[[1-[3-(trifluoromemyl)phenyl]emylidene]amino]oxy]methyl]phenyl]-3H-1,2,4-
triazol-3-one; and fiusilazole in a mole ratio of the compound of Formula Ia to the
compound of Formula IIa plus fiusilazole of from about 4:1 to 1:4 and the compound of
Formula IIa to fiusilazole has a mole ratio of from about 4:1 to 1:4.
This invention also provides a process for controlling at least one plant disease
selected from wheat powdery mildew, wheat leaf rust, wheat foot rot, and wheat glume
blotch which comprises applying to the plant or portion thereof to be protected, or to the
plant seed or seedling to be protected, an effective amount of a fungicidal combination
including component (1) and component (2) wherein the mole ratio of component (1) to
component (2) is from about 30:1 to 1:30 (preferably from about 4:1 to 1:4).
Component (1) can, for example, be applied at a rate of 0.2 g/ha or more. Typically
component (1) is applied at a rate of 100 g/ha. Component (2) may be applied
simultaneously (e.g., in the form of a composition comprising component (1) and
component (2) in an appropriate mole ratio); or component (1) and component (2) can
be applied separately in an appropriate mole ratio (e.g., as a tank mix).
Compositions wherein component (2) is selected from the group consisting of 2,4-
dihydro-5-methoxy-2-methyI-4-[2-[[[[1-[3-
(trifluoromethyl)phenyl]ethylidene]amino]oxy]methyl]phenyl]-3H-1,2,4-triazol-3-one,
kresoxim-methyl, azoxystrobin, (E)-2-(methoxyimino)-N-methyl-2-(2-
phenoxyphenyl)acetamide, flusilazole, epoxiconazole, fenpropimorph, propiconazole
and tebuconazole; and wherein the mole ratio of component (1) to component (2) is
from about 4:1 to 1:10 are considered especially useful for controlling wheat powdery
mildew. Preferred component (1) compounds for these compositions include
6-bromo-3-propyl-2-propyloxy-4(3H)-quinazolinone;
6,8-diiodo-3-propyl-2-propyloxy-4(3H)-quinazolinone;and
6-iodo-3 -propy l-2-propyloxy-4(3H)-quinazolinone; with
6-iodo-3-propyl-2-propyloxy-4(3H)-quinazolinone being particularly preferred.
Preferred component (2) compounds for these compositions include 2,4-dihydro-5-
methoxy-2-methyl-4-[2-[[[[1-[3-
(trifluoromemyl)phenyl]emylidene]amino]oxy]methyl]phenyI]-3H-1,2,4-triazol-3-one,
fenpropimorph, flusilazole, epoxiconazole and propiconazole. Example compositions
of this type include compositions comprising
6-iodo-3 -propyl-2-propyloxy-4(3H)-quinazolinone and 2,4-dihydro-5-methoxy-2-
methyl-4-[2-[[[[1-[3-(trifluoromethyl)phenyl]ethylidene]amino]oxy]methyl]phenyl]-3H-
1,2,4-triazol-3-one in a mole ratio of the compound of Formula Ia to the compound of
Formula IIa of from about 4:1 to 1:4, compositions comprising
6-iodo-3-propyl-2-propyloxy-4(3H)-quinazolinone and fenpropimorph in a mole ratio of
the compound of Formula Ia to fenpropimorph of from about 1:1 to 1:10, compositions
comprising 6-iodo-3-propyl-2-propyloxy-4(3H)-quinazolinone and flusilazole in a mole
ratio of the compound of Formula Ia to flusilazole of from about 4:1 to 1:4, and
compositions comprising 6-iodo-3-propyl-2-propyloxy-4(3H)-quinazolinone; 2,4-
dihydro-5-methoxy-2-methyl-4-[2-[[[[1-[3-
(trifluoromemyl)phenyl]ethylidene]amino]oxy]methyl]phenyl]-3H-1,2,4-triazol-3-one;
and flusilazole in a mole ratio of the compound of Formula Ia to the total of the
compound of Formula IIa plus flusilazole of from about 4:1 to 1:4 and a mole ratio of
the compound of Formula IIa to flusilazole of from about 4:1 to 1:4.
This invention also provides a process for controlling wheat powdery mildew
which comprises applying to the plant or portion thereof to be protected, or to the plant
seed or seedling to be protected, an effective amount of a fungicidal combination
including component (1) and component (2) wherein the mole ratio of component (1) to
component (2) is from about 4:1 to 1:10 (preferably from about 4:1 to 1:4).
Component (1) can, for example, be applied at a rate of 0.2 g/ha or more. Typically
component (1) is applied at a rate of 100 g/ha. Component (2) may be applied
simultaneously (e.g., in the form of a composition comprising component (1) and
component (2) in an appropriate mole ratio); or component (1) and component (2) can
be applied separately in an appropriate mole ratio (e.g., as a tank mix).
Compositions wherein component (2) is selected from the group consisting of 2,4-
dihydro-5-methoxy-2-methyl-4-[2-[[[[1-[3-
(trifluoromethyl)phenyl]ethylidene]amino]oxy]methyl]phenyl]-3H-1,2,4-triazol-3-one,
kresoxim-methyl, azoxystrobin, (E)-2-(methoxyimino)-N-methyl-2-(2-
phenoxyphenyl)acetamide, flusilazole, epoxiconazole, fenpropimorph, propiconazole
and tebuconazole; and wherein the mole ratio of component (1) to component (2) is
from about 30:1 to 1:30 are considered especially useful for controlling wheat leaf rust.
Preferred component (1) compounds for these compositions include
6-bromo-3-propyl-2-propyloxy-4(3H)-quinazolinone;
6,8-diiodo-3-propyl-2-propyloxy-4(3H)-quinazolinone; and
6-iodo-3-propyl-2-propyloxy-4(3H)-quinazolinone; with
6-iodo-3-propyl-2-propyloxy-4(3H)-quinazolinone being particularly preferred being
particularly preferred. Preferred component (2) compounds for these compositions
include 2,4-dihydro-5-methoxy-2-methyl-4-[2-[[[[1 -[3-
(trifluoromethyl)phenyl]ethylidene]amino]oxy]methyl]phenyl]-3H-1,2,4-triazol-3-one,
epoxiconazole, flusilazole and tebuconazole; with flusilazole and epoxiconazole being
particularly preferred. Preferably, the mole ratio of component (1) to component (2) for
these compositions if from about 4:1 to 1:4. Example compositions of this type include
compositions comprising 6-iodo-3-propyl-2-propyloxy-4(3H)-quinazolinone and
flusilazole in a mole ratio of the compound of Formula Ia to flusilazole of from about
15:1 to 1:15, compositions comprising
6-iodo-3 -propyl-2-propyloxy-4(3H)-quinazolinone and tebuconazole in a mole ratio of
the compound of Formula Ia to tebuconazole from about 30:1 to 1:30.
This invention also provides a process for controlling wheat leaf rust which
comprises applying to the plant or portion thereof to be protected, or to the plant seed or
seedling to be protected, an effective amount of a fungicidal combination including
component (1) and component (2) wherein the mole ratio of component (1) to
component (2) is from about 30:1 to 1:30 (preferably from about 4:1 to 1:4).
Component (2) can, for example, be applied at a rate of 12.5 g/ha or more. Typically
component (2) is applied at a rate of 160 g/ha. Component (1) may be applied
simultaneously (e.g., in the form of a composition comprising component (1) and
component (2) in an appropriate mole ratio); or component (1) and component (2) can
be applied separately in an appropriate mole ratio (e.g., as a tank mix).
Compositions wherein component (2) is selected from the group consisting of 2,4-
dihydro-5-methoxy-2-methyl-4-[2-[[[[1-[3-
(trifluoromethyl)phenyl]ethylidene]amino]oxy]methyl]phenyl]-3H-1,2,4-triazol-3-one,
kresoxim-methyl, azoxystrobin, (E)-2-(methoxyimino)-Ar-methyl-2-(2-
phenoxyphenyl)acetamide, flusilazole, epoxiconazole, fenpropimorph, propiconazole
and tebuconazole; and wherein the mole ratio of component (1) to component (2) is
from about 15:1 to 1:15 are considered especially useful for controlling wheat foot rot.
Preferred component (1) compounds for these compositions include
6-bromo-3-propyl-2-propyloxy-4(3H)-quinazolinone;
6,8-diiodo-3-propyl-2-propyloxy-4(3H)-quinazolinone; and
6-iodo-3-propyl-2-propyloxy-4(3H)-quinazolinone; with
6-iodo-3-propyl-2-propyloxy-4(3H)-quinazolinone being particularly preferred being
particularly preferred. A particularly preferred component (2) compound for these
compositions is flusilazole. Preferably, the mole ratio of component (1) to component
(2) for these compositions if from about 4:1 to 1:4. Example compositions of this type
include compositions comprising 6-iodo-3-propyl-2-propyloxy-4(3H)-quinazolinone
and flusilazole in a mole ratio of the compound of Formula Ia to flusilazole of from
about 15:1 to 1:15.
This invention also provides a process for controlling wheat foot rot which
comprises applying to the plant or portion thereof to be protected, or to the plant seed or
seedling to be protected, an effective amount of a fungicidal combination including
component (1) and component (2) wherein the mole ratio of component (1) to
component (2) is from about 15:1 to 1:15 (preferably from about 4:1 to 1:4).
Component (1) can, for example, be applied at a rate of 5 g/ha or more. Typically
component (1) is applied at a rate of 100 g/ha. Component (2) may be applied
simultaneously (e.g., in the form of a composition comprising component (1) and
component (2) in an appropriate mole ratio); or component (1) and component (2) can
be applied separately in an appropriate mole ratio (e.g., as a tank mix).
Compositions wherein component (2) is selected from the group consisting of 2,4-
dihydro-5-methoxy-2-methyl-4-[2-[[[[1-[3-
(trifluoromemyl)phenyl]emylidene]amino]oxy]methyl]phenyl]-3H-1,2,4-triazol-3 -one,
kresoxim-methyl, azoxystrobin, (E)-2-(methoxyimino)-N-methyl-2-(2-
phenoxyphenyl)acetamide, flusilazole, epoxiconazole, fenpropimorph, propiconazole
and tebuconazole; and wherein the mole ratio of component (1) to component (2) is
from about 30:1 to 1:30 are considered especially useful for controlling wheat glume
blotch. Preferred component (1) compounds for these compositions include
6-bromo-3-propyl-2-propyloxy-4(3H)-quinazolinone;
6,8-diiodo-3 -propyl-2-propyloxy-4(3H)-quinazolinone; and
6-iodo-3-propyl-2-propyloxy-4(3H)-quinazolinone; with
6-iodo-3-propyl-2-propyloxy-4(3H)-quinazolinone being particularly preferred being
particularly preferred. Preferred component (2) compounds for these compositions
include flusilazole and tebuconazole; with flusilazole being particularly preferred.
Preferably, the mole ratio of component (1) to component (2) for these compositions if
from about 4:1 to 1:4. Example compositions of this type include compositions
comprising 6-iodo-3-propyl-2-propyloxy-4(3H)-quinazolinone and tebuconazole in a
mole ratio of the compound of Formula Ia to tebuconazole from about 30:1 to 1:30
This invention also provide a process for controlling wheat glume blotch which
comprises applying to the plant or portion thereof to be protected, or to the plant seed or
seedling to be protected, an effective amount of a fungicidal combination including
component (1) and component (2) wherein the mole ratio of component (1) to
component (2) is from about 30:1 to 1:30 (preferably from about 4:1 to 1:4).
Component (2) can, for example, be applied at 12.5 g/ha or more. Typically component
(2) is applied at a rate of 160 g/ha. Component (1) may be applied simultaneously (e.g.,
in the form of a composition comprising component (1) and component (2) in an
appropriate mole ratio); or component (1) and component (2) can be applied separately
in an appropriate mole ratio, e.g., as a tank mix.
Synthesis of Compounds of Formula I
The compounds of Formula I where D is O can be prepared as described in
International Patent Application WO 94/26722 and as shown in Scheme 1.
An anthranilic acid (2-aminobenzoic acid) of Formula 1 is condensed with an
isothiocyanate of Formula PJ-NCS to form the 2-thioquinazolinedione of Formula 2.
This condensation is preferably performed in the presence of a base such as
triethylamine. S-Methylation of this compound affords the 2-methylthio-
4(3H)-quinazolinone of Formula 3.
For the introduction of the R2O group, the 2-methylthio-4(3H)-quinazolinone of
Formula 3 is treated with a mixture of a base, for example sodium hydride, in R2OH
solvent. The reaction mixture is stirred at a temperature from about 0 °C to 120 °C for
1-120 hours. The desired 2-R2O-4(3H)-quinazolinone can be isolated from the reaction
mixture by extraction into a water-immiscible solvent, and purified by chromatography
or recrystallization. Similar synthetic procedures are described in U.S. 3,755,582,
incorporated herein by reference.
Anthranilic acids of Formula 1 are known or can be prepared by known methods.
For example see, March, J. Advanced Organic Chemistry; 3rd ed., John Wiley:
New York, (1985), p 983. The isothiocyanates of Formula R^-NCS can be prepared
from the corresponding amine by treatment with thiophosgene as known in the art. For
example, see J. Heterocycl. Chem., (1990), 27,407.
6-Iodo-3-propyl-2-propyloxy-4(3H)-quinazolinone, Formula Ia, is a compound of
Formula I where D is O, R1 is propyl, R2 is propyl, R3 is iodine fixed in the 6 position
and R4 is hydrogen.
Synthesis of Compounds of Formula II
Compounds of Formula II where Q is Q-1 and X is OR11 can be prepared as
described in International Patent Application WO 95/14009 by treating a compound of
Formula 4 with an appropriate alkyl transfer reagent in an inert solvent with or without
additional acidic or basic reagents or other reagents (Scheme 2). Suitable solvents are
selected from the group consisting of polar aprotic solvents such as acetonitrile,
dimethylformamide or dimethylsulfoxide; ethers such as tetrahydrofuran,
dimethoxyethane, or diethyl ether; ketones such as acetone or 2-butanone; hydrocarbons
such as toluene or benzene; and halocarbons such as dichloromethane or chloroform.

For example, compounds of Formula II where Q is Q-l and X is OR11 can be
prepared by the action of diazoalkane reagents of Formula 5 such as diazomethane
(V = H) or trimethylsilyldiazomethane (V = (CH3)3Si) on of Formula 4 (Method 1).
Use of trimethylsilyldiazomethane requires a protic cosolvent such as methanol. For
examples of these procedures, see Chem. Pharm. Bull, (1984), 32, 3759.
As indicated in Method 2, compounds of Formula II where Q is Q-1 and X is
OR11 can also be prepared by contacting compounds of Formula 4 with alkyl
trichloroacetimidates of Formula 6 and a Lewis acid catalyst. Suitable Lewis acids
include trimethylsilyl triflate and tetrafluoroboric acid. The alkyl trichloroacetimidates
can be prepared from the appropriate alcohol and trichloroacetonitrile as described in
the literature (J. Danklmaier and H. Honig, Synth. Commun., (1990), 20, 203).
Compounds of Formula II where Q is Q-l and X is OR11 can also be prepared
from compounds of Formula 4 by treatment with a trialkyloxonium tetrafluoroborate
(i.e., Meerwein's salt) of Formula 7 (Method 3). The use of trialkyloxonium salts as
powerful alkylating agents is well known in the art (see U. Schollkopf, U. Groth, C.
Deng, Angew. Chem., Int. Ed. Engl, (1981), 20, 798).
Other alkylating agents which can convert compounds of Formula 4 to
compounds of Formula II where Q is Q-l and X is OR11 are dialkyl sulfates such as
dimethyl sulfate, haloalkyl sulfonates such as methyl trifluoromethanesulfonate, and
alkyl halides such as iodomethane and propargyl bromide (Method 4). These
alkylations can be conducted with or without additional base. Appropriate bases include
alkali metal alkoxides such as potassium tert-butoxide, inorganic bases such as sodium
hydride and potassium carbonate, or tertiary amines such as triethylamine, pyridine,
l,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and triethylenediamine. See R. E. Benson,
T. L. Cairns, J. Am. Chem. Soc, (1948), 70,2115 for alkylation examples using agents
of this type.
Compounds of Formula II where Q is Q-l and X is OR11 can also be prepared by
reaction of Formula 8 compounds with alkali metal alkoxides (R11O-M+) (Scheme 3).
The leaving group Lg1 in the amides of Formula 8 are any group known in the art to
undergo a displacement reaction of this type. Examples of suitable leaving groups
include chlorine, bromine, and sulfonyl and sulfonate groups. Examples of suitable
inert solvents are dimethylformamide or dimethylsulfoxide.

2,4-Dihydro-5-methoxy-2-methyl-4-[2-[[[[1-[3-
(trifluoromethyl)phenyl]ethylidene]amino]oxy]methyl]phenyl]-3H-1,2,4-triazol-3-one,
Formula IIa, is a compound of Formula II where Q is Q-1, E is 1,2-phenylene, A is N,
G is N with the floating double bond attached to A, W is O, X is OR11, R11 is CH3,
R12 is CH3, Y is -CHR25O-N=C(R17)-, R17 is CH3, R25 is H, Z is phenyl substituted
with R19 and R19 is CF3 fixed in the 3 position.

Azoxystrobin, Formula IIb, is a compound of Formula II where Q is Q-2,
E is 1,2 phenylene, W1 is O, X1 is C, Y is -O-, Z is 4,6-pyrimidinyl substituted with
R19, R19 is phenoxy substituted with R21 and R21 is cyano fixed in the 2 position.
Kresoxim-methyl, Formula IIc, is a compound of Formula II where Q is Q-2,
E is 1,2-phenylene, W1 is O, X1 is N, Y is -CHR25O-, R25 is H, Z is phenyl substituted
with R19 and R19 is CH3 fixed in the 2 position.
(E)-2-(methoxyimino)-N-methyl-2-(2-phenoxyphenyl)acetamide, Formula IId, is a
compound of Formula II where Q is Q-2, E is 1,2-phenylene, W1 is NH, X1 is N,
Y is -O-, Z is phenyl substituted with R19 wherein R19 is H.
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.
Formulation/Utility
The fungicidal compositions of the present invention comprise an effective
amount of a mixture of the compounds(s) of component (1) (e.g.,
6-iodo-3-propyl-2-propyloxy-4(3H)-quinazolinone) and the compound(s) of
component (2) (e.g., 2,4-dihydro-5-methoxy-2-methyl-4-[2-[[[[1-[3-
(trifluoromethyl)phenyl]emylidene]amino]oxy]methyl]phenyl]-3H-1,2,4-triazol-3 -one,
kresoxim-methyl, azoxystrobin, (E)-2-(methoxyimino)-N-methyl-2-(2-
phenoxyphenyl)acetamide, flusilazole, epoxiconazole, fenpropimorph, propiconazole
and/or tebuconazole). The mixtures of this invention will typically 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 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, 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 encapsulate (or "overcoated"). Encapsulation can control or delay release of the active ingredient.
Sprayable formulations can be extended in suitable media and used 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 ingredients,
diluent and surfactant within the following approximate ranges which add up to 100
percent by weight.

Typical solid diluents are described in Watkins, et al., Handbook of Insecticide
Dust 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 andEmulsifiers Annual, Allured Publ. Corp.,
Ridgewood, New Jersey, as well as Sisely and Wood, Encyclopedia of Surface Active
Agents, Chemical Publ. 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
alkylphenols, polyethoxylated sorbitan fatty acid esters, dialkyl sulfosuccinates, alkyl
sulfates, alkylbenzene sulfonates, organosilicones, N,N-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, diatomaceous earth, urea, calcium carbonate, sodium carbonate and
bicarbonate, and sodium sulfate. Liquid diluents include, for example, water,
N,N-dirnethylformamide, dimethyl sulfoxide, N-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 cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-
methyl-2-pentanone, and alcohols such as methanol, cyclohexanol, decanol and
terrahydrofurfuryl 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 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 International Patent Publication WO
91/13546. Pellets can be prepared as described in U.S. Patent No. 4,172,714.
Water-dispersible and water-soluble granules can be prepared as taught in
U.S. Patent No. 4,144,050, U.S. Patent No. 3,920,442 and German Patent Application
DE 3,246,493. Tablets can be prepared as taught in U.S. Patent No. 5,180,587,
U.S. Patent No. 5,232,701 and U.S. Patent No. 5,208,030. Films can be prepared as
taught in Great Britain Patent Application GB 2,095,558 and U.S. Patent No. 3,299,566.
For further information regarding the art of formulation, see
U.S. Patent No. 3,235,361, Col. 6, line 16 through Col. 7, line 19 and Examples 10-41;
U.S. Patent No. 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. Patent No. 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
Publications, Oxford, 1989.
In the following Examples, all percentages are by weight and all formulations are
prepared in conventional ways.
The compounds of this invention are useful as plant disease control agents. The
present invention therefore further comprises a method for controlling plant diseases
caused by fungal plant pathogens comprising applying to the plant or portion thereof to
be protected, or to the plant seed or seedling Id be protected, an effective amount of a
compound of the invention or a fungicidal composition containing said compound. The
compounds and compositions of this invention provide control of diseases caused by a
broad spectrum of fungal plant pathogens in the Basidiomycete, Ascomycete, Oomycete
and Deuteromycete classes. They are effective in controlling a broad spectrum of plant
diseases, particularly foliar pathogens of ornamental, vegetable, field, cereal, and fruit
crops. These pathogens include Plasmopara viticola, Phytophthora infestans,
Peronospora tabacina, Pseudoperonospora cubensis, Pythium aphanidermatum,
Alternaria brassicae, Septoria nodorum, Septoria tritici, Cercosporidium personatum,
Cercospora arachidicola, Pseudocercosporella herpotrichoides, Cercospora beticola,
Botrytis cinerea, Monilinia fructicola, Pyricularia oryzae, Podosphaera leucotricha,
Venturia inaequalis, Erysiphe graminis, Uncinula necatur, Puccinia recondita,
Puccinia graminis, Hemileia vastatrix, Puccinia striiformis, Puccinia arachidis,
Rhizocionia solani, Sphaerotheca fuliginea, Fusarium oxysporum, Verticillium dahliae,
Pythium aphanidermatum, Phytophthora megasperma, Sclerotinia sclerotiorum,
Sclerotium rolfsii, Erysiphe polygoni, Pyrenophora teres, Gaeumannomyces graminis,
Rynchosporium secalis, Fusarium roseum, Bremia lactucae and other generea and
species closely related to these pathogens.
Mixtures of this invention can be further 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 agricultural protection. Examples of such agricultural
protectants with which compounds of this invention can be formulated are: insecticides
such as abamectin, acephate, azinphos-methyl, bifenthrin, buprofezin, carbofuran,
chlorfenapyr, chlorpyrifos, chlorpyrifos-methyl, cyfluthrin, beta-cyfluthrin, cyhalothrin,
lambda-cyhalothrin, deltamethrin, diafenthiuron, diazinon, diflubenzuron, dimethoate,
esfenvalerate, fenoxycarb, fenpropathrin, fenvalerate, fipronil, flucythrinate,
tau-fluvalinate, fonophos, imidacloprid, isofenphos, malathion, metaldehyde,
methamidophos, methidathion, methomyl, methoprene, methoxychlor, methyl 7-chloro-
2,5-dihydro-2-[[Ar-(methoxycarbonyl)-iV-[4-
(trifluoromethoxy)phenyl]amino]carbonyl]indeno[ 1,2-e] [ 1,3,4]oxadiazine-4a(3H)-
carboxylate (DPX-JW062), monocrotophos, oxamyl, parathion, parathion-methyl,
permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos,
rotenone, sulprofos, tebufenozide, tefluthrin, terbufos, tetrachlorvinphos, thiodicarb,
tralomethrin, trichlorfon and triflumuron; fungicides such as benomyl, blasticidin-S,
Bordeaux mixture (tribasic copper sulfate), captafol, captan, carbendazim, chloroneb,
chlorothalonil, copper oxychloride, copper salts, cymoxanil, cyprodinil (CGA 219417),
diclomezine, dicloran, dimethomorph, dodine, edifenphos, famoxadone, fenpiclonil,
fluazinam, flutolanil, folpet, fosetyl-aluminum, furalaxyl, iprobenfos, iprodione,
isoprothiolane, kasugamycin, mancozeb, maneb, mepronil, metalaxyl, S-methyl
7-benzothiazolecarbothioate (CGA 245704), myclobutanil, neo-asozin (ferric
methanearsonate), oxadixyl, pencycuron, probenazole, prochloraz, pyrifenox,
pyroquilon, quinoxyfen, spiroxamine (KWG4168), sulfur, thiabendazole,
thiophanate-methyl, thiram, tricyclazole, validamycin and vinclozolin; nematocides
such as aldoxycarb and fenamiphos; bactericides such as streptomycin; acaricides such
as amitraz, chinomethionat, chlorobenzilate, cyhexatin, dicofol, dienochlor, etoxazole,
fenazaquin, fenbutatin oxide, fenpropathrin, fenpyroximate, hexythiazox, propargite,
pyridaben and tebufenpyrad; and biological agents such as Bacillus thuringiensis,
Bacillus thuringiensis delta endotoxin, baculovirus, and entomopathogenic bacteria,
virus and fungi.
In certain instances, combinations with other fungicides having a similar spectrum
of control but a different mode of action will be particularly advantageous for resistance
management.
Plant disease control is ordinarily accomplished by applying an effective amount
of the composition of this invention either pre— or post—infection, to the portion of the
plant to be protected such as the roots, stems, foliage, fruit, seeds, tubers or bulbs, or to
the media (soil or sand) in which the plants to be protected are growing. The
composition can also be applied to the seed to protect the seed and seedling.
Rates of application for this composition can be influenced by many factors of the
environment and should be determined under actual use conditions. Foliage can
normally be protected when treated at a rate of from less than 1 g/ha to 5,000 g/ha of
aggregate active ingredient. Aggregate active ingredient is defined as the total
combined weight of active ingredients. Seed and seedlings can normally be protected
when seed is treated at a rate of from 0.1 to 10 g of aggregate active ingredient per
kilogram of seed.
The following Examples demonstrate the composition and method of the present
invention and provide experimental evidence for synergy between the compound of
Formula Ia and flusilazole in preventative control of wheat leaf rust caused by Puccinia
recondita, wheat foot rot caused by Pseudocercosporella herpotrichoides, and wheat
glume blotch caused by Septoria nodorum. The experimental also provides evidence
for synergy between the compound of Formula Ia and tebuconazole in preventative
control of wheat leaf rust and wheat glume blotch. The experimental also provides
evidence for synergy between the compound of Formula Ia and flusilazole in curative
control of wheat powdery mildew caused by Erysiphe graminisf. sp. tritici and wheat
leaf rust.
The experimental also provides evidence for synergy between he compounds of
Formula Ia, Formula IIa and flusilazole in preventative control of wheat foot rot. The
experimental also provides evidence for synergy between the compounds of Formula Ia,
IIa and flusilazole in curative control of wheat powdery mildew. The pathogen control
protection afforded by these compositions is not limited, however, to these species.
The following TESTS demonstrate the control efficacy of compounds of this
invention on specific pathogens. The pathogen control protection afforded by the
compounds is not limited, however, to these species.
BIOLOGICAL EXAMPLES OF THE INVENTION
Test compounds were first dissolved in acetone in an amount equal to 50% of the
final volume and then suspended at a concentrations from 0.08 to 200 ppm in purified
water containing 250 ppm of the surfactant Trem® 014 (polyhydric alcohol esters).
The resulting test suspensions were then used in the following test protocols. Spraying
these test suspensions to the point of run-off on the test plants is the equivalent of a rate
of 500 g/ha.
Protocol # 1 - WPM Preventive
The test compounds were sprayed to the point of run-off on wheat seedlings. The
following day the seedlings were inoculated with a spore dust of Erysiphe graminis
f. sp. tritici, (the causal agent of wheat powdery mildew). Seedlings were incubated in a
growth chamber at 20 °C for 6 days, after which disease ratings were made.
Protocol # 2 - WPM Curative
Wheat seedlings were inoculated with a spore dust of Erysiphe graminis
f. sp. tritici, (the causal agent of wheat powdery mildew). The following day a test
compounds were sprayed to the point of run-off on and seedlings incubated in a
growthchamber at 20 °C for 7 days, after which disease ratings were made.
Protocol # 3 WLR Preventive
The test compounds were sprayed to the point of run-off on wheat seedlings. The
following day the seedlings were inoculated with a spore suspension of Puccinia
recondita (the causal agent of wheat leaf rust) and incubated in a saturated atmosphere
at 20 °C for 24 h, and then moved to a growth chamber at 20 °C for 6 days, after which
disease ratings were made.
Protocol # 4 - WLR Curative
Wheat seedlings were inoculated with a spore suspension of Puccinia recondita
(the causal agent of wheat leaf rust). The following day the test compounds were
sprayed to the point of run-off on and incubated in a saturated atmosphere at 20 °C for
24 h, then moved to a growth chamber at 20 °C for 6 days, after which disease ratings
were made.
Protocol # 5 - WFR Preventive
The test compounds were sprayed to the point of run-off on wheat seedlings. The
following day the seedlings were inoculated with a spore suspension of
Pseudocercosporella herpotrichoides (the causal agent of wheat eye spot or wheat foot
rot) and incubated in a saturated atmosphere at 20 °C for 72 h, and then moved to a
growth chamber at 20 °C for 6 days, after which disease ratings were made.
Protocol # 6 - WGB Preventive
The test compounds were sprayed to the point of run-off on wheat seedlings. The
following day the seedlings were inoculated with a spore suspension of Septoria
nodorum (the causal agent of wheat glume blotch) and incubated in a saturated
atmosphere at 20 °C for 48 h, and then moved to a growth chamber at 20 °C for 6 days,
after which disease ratings were made.
Protocol # 7 - WGB Curative
Wheat seedlings were inoculated with a spore suspension Septoria nodorum (the
causal agent of wheat glume blotch). Two days later test compounds were sprayed to
the point of run-off on and seedlings incubated in a saturated atmosphere at 20 °C for
48 h, then moved to a growth chamber at 20 °C for 6 days, after which disease ratings
were made.
Protocol # 8 - WPM Preventative
The test suspension was sprayed to the point of run-off on wheat seedlings. The
following day the seedlings were inoculated with a spore dust of Erysiphe graminis
f. sp. tritici, (the causal agent of wheat powdery mildew) and incubated in a growth
chamber at 20 °C for 7 days, after which disease ratings were made.
Results for protocols 1 - 8 are given in Tables A-G. In the tables, a rating of 100
indicates 100% disease control and a rating of 0 indicates no disease control (relative to
the controls). An (nt) indicates no test results and (--) indicates no estimate of activity.
In Tables A-G rates are given in parts per million (ppm) and/or grams active ingredient
per hectare (g a.i./ha). The term "Actual" stands for the experimental value. The
abbreviation "Exp." stands for "Expected" (i.e., the predicted activity, p, from the Colby
equation).
We Claim:
1. A fungicidal composition comprising:
(1) at least one quinazolinone of Formula 1 including all geometric and
stereoisomers, N-oxides, and agriculturally suitable salts thereof,

wherein
D is O or S;
R1 is C1-C6 alkyl;
R2 is C1-C6 alkyl;
R3 is halogen; and
R4 is hydrogen or halogen;
(2) at least one component which is at least one compound selected from
compounds that controls fungal disease by inhibiting the sterol biosynthesis and
optionally
(3) at least one of a surfactant, a solid diluent or a liquid diluent;
wherein component (1) and component (2) are present in fungicidally effective amount
and the mole ratio of component (1) to component (2) is from 30:1 to 1:30.
2. A fungicidal composition as claimed in claim 1 wherein component (1) has the formula

wherein R1 and R2 are both propyl, R3 is iodine and R4 is iodine or hydrogen, or R3 is
bromine and R is hydrogen.
3. A fungicidal composition as claimed in any one of the claims 1 or 2 wherein component
(2) is selected from DMI compounds.
4. A fungicidal composition as claimed in claim 3 wherein component (2) is selected from
triazoles.
5. A fungicidal composition as claimed in claim 4 wherein component (2) is selected from
flusilazole, epiconazole, propiconazole and tebuconazole.
6. A fungicidal composition as claimed in claim 5 wherein component (2) is tebuconazole.
7. A fungicidal composition as claimed in any of claims 1 to 6 wherein the weight ratio of
component (1) to component (2) is from about 4:1 to 1:4.
8. A fungicidal composition as claimed in any of claims 1 through 7 wherein component (1)
is 6-iodo-3-propyl-2-propyloxy-4(3H)-quinazolinone.
9. A fungicidal composition as hereinbefore described and illustrated with reference to the
foregoing examples.

A fungicidal composition comprising:
(1) at least one quinazolinone of Formula 1 including all geometric and
stereoisomers, N-oxides, and agriculturally suitable salts thereof,

wherein
D is O or S;
R1 is C1-C6 alkyl;
R2 is C1-C6 alkyl;
R3 is halogen; and
R4 is hydrogen or halogen;
(2) at least one component which is at least one compound selected from
compounds that controls fungal disease by inhibiting the sterol biosynthesis and
optionally
(3) at least one of a surfactant, a solid diluent or a liquid diluent;
wherein component (1) and component (2) are present in fungicidally effective amount
and the mole ratio of component (1) to component (2) is from 30:1 to 1:30.

Documents:

01313-kol-2006 abstract.pdf

01313-kol-2006 claims.pdf

01313-kol-2006 correspondenceothers.pdf

01313-kol-2006 description(complete).pdf

01313-kol-2006 form1.pdf

01313-kol-2006 form2.pdf

01313-kol-2006 form3.pdf

01313-kol-2006 form5.pdf

01313-kol-2006-correspondence-1.1.pdf

01313-kol-2006-form-18.pdf

1313-KOL-2006-(09-05-2012)-CORRESPONDENCE.pdf

1313-KOL-2006-(09-05-2012)-PA.pdf

1313-KOL-2006-ABSTRACT 1.1.pdf

1313-KOL-2006-ABSTRACT-1.2.pdf

1313-KOL-2006-AMANDED CLAIMS.pdf

1313-KOL-2006-CANCELLED PAGES-1.1.pdf

1313-KOL-2006-CANCELLED PAGES.pdf

1313-KOL-2006-CLAIMS 1.1.pdf

1313-KOL-2006-CORRESPONDENCE 1.1.pdf

1313-KOL-2006-CORRESPONDENCE-1.3.pdf

1313-kol-2006-correspondence.pdf

1313-KOL-2006-DESCRIPTION (COMPLETE) 1.1.pdf

1313-KOL-2006-DESCRIPTION (COMPLETE)-1.2.pdf

1313-kol-2006-examination report.pdf

1313-KOL-2006-FORM 1.pdf

1313-kol-2006-form 18.pdf

1313-KOL-2006-FORM 2-1.2.pdf

1313-KOL-2006-FORM 2.1.1.pdf

1313-KOL-2006-FORM 3.1.1.pdf

1313-kol-2006-form 3.pdf

1313-kol-2006-form 5.pdf

1313-kol-2006-granted-abstract.pdf

1313-kol-2006-granted-claims.pdf

1313-kol-2006-granted-description (complete).pdf

1313-kol-2006-granted-form 1.pdf

1313-kol-2006-granted-form 2.pdf

1313-kol-2006-granted-specification.pdf

1313-KOL-2006-INTENATIONAL PUBLICATION.pdf

1313-kol-2006-others-1.1.pdf

1313-KOL-2006-OTHERS.pdf

1313-kol-2006-pa-1.1.pdf

1313-KOL-2006-PA.pdf

1313-KOL-2006-PETITION UNDER RULE 137.pdf

1313-kol-2006-reply to examination report-1.1.pdf

1313-KOL-2006-REPLY TO EXAMINATION REPORT.pdf

1321-KOL-2009-CORRESPONDENCE 1.2.pdf

1321-KOL-2009-FORM 3 1.2.pdf

abstract-01313-kol-2006.jpg


Patent Number 246819
Indian Patent Application Number 1313/KOL/2006
PG Journal Number 11/2011
Publication Date 18-Mar-2011
Grant Date 16-Mar-2011
Date of Filing 07-Dec-2006
Name of Patentee E.I .DU PONT DE NEMOURS AND COMPANY
Applicant Address WILMINGTON, DELAWARE
Inventors:
# Inventor's Name Inventor's Address
1 MARTINA CAJNAR CROMPTON 6178 TELEGRAPH ROAD, ELKTON, MARYLAND 21921
2 ANTHONY JAY JULIS 2706 Doris Drive,Wilmington,Delaware 19803
3 STEPHEN RAY FLOOR 508 Hemingway Drive, Hochessin,Delaware 19707
PCT International Classification Number A01N 43/40
PCT International Application Number N/A
PCT International Filing date
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 60/036063 1997-01-30 U.S.A.