Fungicides for the control of take-all disease of plants
First Claim
1. A method of controlling disease in a plant caused by Gaeumannomyces sp. comprising applying to the plant locus a fungicidally effective amount of a fungicide of the formula ##STR3## wherein Z1 and Z2 are C and are part of an aromatic ring which is thiophene;
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B is --Wm Q(R2)3 ;
or selected from o-tolyl, 1-naphthyl, 2-naphthyl, and 9-phenanthryl, each optionally substituted with halogen or R4 ;
Q is C or Si;
W is --C(R3)p H.sub.(2-p) -- or when Q is C, W is selected from --C(R3)p H.sub.(2-p) --, --N(R3)m H.sub.(1-m) --, --S(O)p --, and --O--;
X is O;
n is 2;
m is 0 or 1;
p is 0, 1, or 2;
wherein the two R groups are alkenyl groups and are combined to form a fused ring with the thiophene ring which is benzothiophene;
wherein the alkenyl groups are optionally substituted with halo, hydroxy, thio, amino, nitro, cyano, formyl, phenyl, C1 -C4 alkoxy, alkylcarbonyl, alkylthio, alkylamino, dialkylamino, alkoxycarbonyl, (alkylthio)carbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylsulfinyl, or alkylsulfonyl;
each R2 is independently selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, and phenyl, each optionally substituted with R4 or halogen; and
wherein, when Q is C, R2 may also be selected from halo, alkoxy, alkylthio, alkylamino, and dialkylamino;
or wherein two R2 groups may be combined to form a cyclo group with Q;
R3 is C1 -C4 alkyl;
R4 is C1 -C4 alkyl, haloalkyl, alkoxy, alkylthio, alkylamino, or dialkylamino;
or an agronomic salt thereof.
1 Assignment
0 Petitions
Accused Products
Abstract
A method of controlling Take-all disease of plants by applying, preferably to the seed prior to planting, a fungicide of the formula ##STR1## wherein Z1 and Z2 are C or N and are part of an aromatic ring selected from benzene, pyridine, thiophene, furan, pyrrole, pyrazole, thiazole, and isothiazole;
A is selected from --C(X)-amine, --C(O)--SR3, --NH--C(X)R4, and --C(═NR3)--XR7 ;
B is --Wm --Q(R2)3 or selected from o-tolyl, 1-naphthyl, 2-naphthyl, and 9-phenanthryl, each optionally substituted with halogen or R4 ;
Q is C, Si, Ge, or Sn;
W is --C(R3)p H.sub.(2-p) --; or when Q is C, W is selected from --C(R3)p H.sub.(2-p) --, --N(R3)m H.sub.(1-m) --, --S(O)p --, and --O--;
X is O or S;
n is 0, 1, 2, or 3;
m is 0 or 1;
p is 0, 1, or 2;
each R is independently selected from
a) halo, formyl, cyano, amino, nitro, thiocyanato, isothiocyanato, trimethylsilyl, and hydroxy;
b) C1-C4 alkyl, alkenyl, alkynyl, C3-C6 cycloalkyl, and cycloalkenyl, each optionally substituted with halo, hydroxy, thio, amino, nitro, cyano, formyl, phenyl, C1-C4 alkoxy, alkylcarbonyl, alkylthio, alkylamino, dialkylamino, alkoxycarbonyl, (alkylthio)carbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylsulfinyl, or alkylsulfonyl;
c) phenyl, furyl, thienyl, pyrrolyl, each optionally substituted with halo, formyl, cyano, amino, nitro, C1-C4 alkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkylamino, dialkylamino, haloalkyl, and haloalkenyl;
d) C1-C4 alkoxy, alkenoxy, alkynoxy, C3-C6 cycloalkyloxy, cycloalkenyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonylamino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, (alkylthio)carbonyl, phenylcarbonylamino, phenylamino, each optionally substituted with halo;
wherein two R groups may be combined to form a fused ring;
each R2 is independently selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl and phenyl, each optionally substituted with R4 or halogen; and wherein, when Q is C, R2 may also be selected from halo, alkoxy, alkylthio, alkylamino, and dialkylamino;
wherein two R2 groups may be combined to form a cyclo group with Q;
R3 is C1-C4 alkyl;
R4 is C1-C4 alkyl, haloalkyl, alkoxy, alkylthio, alkylamino, or dialkylamino; and
R7 is C1-C4 alkyl, haloalkyl, or phenyl, optionally substituted with halo, nitro, or R4 ;
or an agronomic salt thereof.
22 Citations
27 Claims
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1. A method of controlling disease in a plant caused by Gaeumannomyces sp. comprising applying to the plant locus a fungicidally effective amount of a fungicide of the formula ##STR3## wherein Z1 and Z2 are C and are part of an aromatic ring which is thiophene;
- and
A is --C(X)-amine wherein the amine is an N-bonded heterocyclic compound chosen from the group consisting of pyrrole, pyrazole imidazole, and triazole, each optionally substituted with C1 -C6 alkyl groups; B is --Wm Q(R2)3 ;
or selected from o-tolyl, 1-naphthyl, 2-naphthyl, and 9-phenanthryl, each optionally substituted with halogen or R4 ;Q is C or Si; W is --C(R3)p H.sub.(2-p) -- or when Q is C, W is selected from --C(R3)p H.sub.(2-p) --, --N(R3)m H.sub.(1-m) --, --S(O)p --, and --O--; X is O; n is 2; m is 0 or 1; p is 0, 1, or 2; wherein the two R groups are alkenyl groups and are combined to form a fused ring with the thiophene ring which is benzothiophene;
wherein the alkenyl groups are optionally substituted with halo, hydroxy, thio, amino, nitro, cyano, formyl, phenyl, C1 -C4 alkoxy, alkylcarbonyl, alkylthio, alkylamino, dialkylamino, alkoxycarbonyl, (alkylthio)carbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylsulfinyl, or alkylsulfonyl;each R2 is independently selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, and phenyl, each optionally substituted with R4 or halogen; and
wherein, when Q is C, R2 may also be selected from halo, alkoxy, alkylthio, alkylamino, and dialkylamino;
or wherein two R2 groups may be combined to form a cyclo group with Q;R3 is C1 -C4 alkyl; R4 is C1 -C4 alkyl, haloalkyl, alkoxy, alkylthio, alkylamino, or dialkylamino; or an agronomic salt thereof. - View Dependent Claims (4, 5, 6, 7, 8, 9, 10, 11, 12, 24, 25)
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2. A compound of the formula ##STR4## wherein Z1 and Z2 are C and are part of an aromatic ring which is thiophene;
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A is --C(X)-amine wherein the amine is an N-bonded heterocyclic compound chosen from the group consisting of pyrrole, pyrazole, imidazole, and triazole, each optionally substituted with C1 -C6 alkyl groups; B is --Wm Q(R2)3 ;
or selected from o-tolyl, 1-naphthyl, 2-naphthyl, and 9-phenanthryl, each optionally substituted with halogen or R4 ;Q is C or Si; W is --C(R3)p H.sub.(2-p) -- or when Q is C, W is selected from --C(R3)p H.sub.(2-p) --, --N(R3)m H.sub.(1-m) --, --S(O)p --, and --O--; X is O; n is 2; m is 0 or 1; p is 0, 1,or 2; wherein the two R groups are alkenyl groups and are combined to form a fused ring with the thiophene ring which is benzothiophene;
wherein the alkenyl groups are optionally substituted with halo, hydroxy, thio, amino, nitro, cyano, formyl, phenyl, C1 -C4 alkoxy, alkylcarbonyl, alkylthio, alkylamino, dialkylamino, alkoxycarbonyl, (alkylthio)carbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylsulfinyl, or alkylsulfonyl;each R2 is independently selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, and phenyl, each optionally substituted with R4 or halogen; and
wherein, when Q is C, R2 may also be selected from halo, alkoxy, alkylthio, alkylamino, and dialkylamino;
or wherein two R2 groups may be combined to form a cyclo group with Q;or an agronomic salt thereof. - View Dependent Claims (3, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 26, 27)
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Specification