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 composition comprising 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 pyridine;
- and A is selected from the group consisting of --C(O)--SR3, --NH--C(X)R4, --C(═
NR3)--XR7 and --C(X)-amine wherein the amine is substituted with an alkylaminocarbonyl and a hydrogen or wherein the amine has a first and a second amine substituent, the first amine, substituent is selected from the group consisting of C1 -C10 straight or branched alkyl, alkenyl, or alkynyl groups or mixtures thereof optionally substituted with one or more halogen, hydroxy, alkoxy, alkylthio, nitrile, alkylsulfonate, haloalkylsulfonate, phenyl, a 5-membered heteroaryl, C3 -C6 cycloalkyl and C5 -C6 cycloalkenyl;
phenyl optionally substituted with one or more C1 -C4 straight or branched alkyl, alkenyl, or alkenyl groups or mixtures thereof, cycloalkyl, cycloalkenyl, haloalkyl, alkoxy and nitro;
C3 -C6 cycloalkyl, C5 -C6 cycloalkenyl, alkoxy, alkenoxy, alkynoxy, dialkylamino, and alkylthio;
and the second amine substituent is selected from the group consisting of hydrogen, C1 -C6 straight or branched alkyl, alkenyl, or alkynyl groups or mixtures thereof optionally substituted with one or more halogen;
hydroxy, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, and dialkylphosphonyl;
B is --Wm --Q(R2)3 or selected from 0-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 may also be selected from --N(R3)m H(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 froma) 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;
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 which is 1-methylcyclopropyl, 1-methylcyclobutyl, 1-methylcyclopentyl, or 1-methylcyclohexyl;
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.
1 Assignment
0 Petitions
Accused Products
Abstract
A compound, composition, and method for controlling Take-all disease of plants by applying to the seed prior to planting, a fungicide of the formula: ##STR1## wherein Z1 and Z2 are C and are part of an aromatic ring which is pyridine; R and n are defined herein; A is selected from the group consisting of --C(O)--SR3, --NH--C(X)R4, --C(═NR3)--XR7, and --C(X)-amine wherein the amine is substituted with with an alkylaminocarbonyl and a hydrogen or wherein the amine has a first and a second amine substituent defined herein; B is --Wm --Q(R2)3 or selected from 0-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 may also be selected from --N(R3)m H(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 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 which is 1-methylcyclopropyl, 1-methylcyclobutyl, 1-methylcyclopentyl, or 1-methylcyclohexyl; 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.
53 Citations
101 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 composition comprising 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 pyridine;
- and A is selected from the group consisting of --C(O)--SR3, --NH--C(X)R4, --C(═
NR3)--XR7 and --C(X)-amine wherein the amine is substituted with an alkylaminocarbonyl and a hydrogen or wherein the amine has a first and a second amine substituent, the first amine, substituent is selected from the group consisting of C1 -C10 straight or branched alkyl, alkenyl, or alkynyl groups or mixtures thereof optionally substituted with one or more halogen, hydroxy, alkoxy, alkylthio, nitrile, alkylsulfonate, haloalkylsulfonate, phenyl, a 5-membered heteroaryl, C3 -C6 cycloalkyl and C5 -C6 cycloalkenyl;
phenyl optionally substituted with one or more C1 -C4 straight or branched alkyl, alkenyl, or alkenyl groups or mixtures thereof, cycloalkyl, cycloalkenyl, haloalkyl, alkoxy and nitro;
C3 -C6 cycloalkyl, C5 -C6 cycloalkenyl, alkoxy, alkenoxy, alkynoxy, dialkylamino, and alkylthio;and the second amine substituent is selected from the group consisting of hydrogen, C1 -C6 straight or branched alkyl, alkenyl, or alkynyl groups or mixtures thereof optionally substituted with one or more halogen;
hydroxy, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, and dialkylphosphonyl;B is --Wm --Q(R2)3 or selected from 0-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 may also be selected from --N(R3)m H(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; 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 which is 1-methylcyclopropyl, 1-methylcyclobutyl, 1-methylcyclopentyl, or 1-methylcyclohexyl;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. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32)
- and A is selected from the group consisting of --C(O)--SR3, --NH--C(X)R4, --C(═
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33. A compound of the formula ##STR4## wherein Z1 and Z2 are C and are part of an aromatic ring which is pyridine;
- and A is selected from the group consisting of --C(O)--SR3, --NH--C(X)R4, --C(═
NR3)--Xr7 and --C(X)-amine wherein the amine is substituted with an alkylaminocarbonyl and a hydrogen or wherein the amine has a first and second amine substituent,the first amine substituent is selected from the group consisting of C1 -C10 straight or branched alkyl, alkenyl, or alkynyl groups or mixtures thereof optionally substituted with one or more halogen, hydroxy, alkoxy, alkylthio, nitrile, alkylsulfonate, haloalkylsulfonate, phenyl, a 5-membered heteroaryl, C3 -C6 cycloalkyl and C5 -C6 cycloalkenyl;
phenyl optionally substituted with one or more C1 -C4 straight or branched alkyl, alkenyl, or alkynyl groups or mixtures thereof, cycloalkyl, cycloalkenyl, haloalkyl, alkoxy and nitro;
C3 -C6 cycloalkyl, C5 -C6 cycloalkenyl, alkoxy, alkenoxy, alkynoxy, dialkylamino, and alkylthio;and the second amine substituent is selected from the group consisting of hydrogen, C1 -C6 straight or branched alkyl, alkenyl, or alkynyl groups or mixtures thereof optionally substituted with one or more halogen;
hydroxy, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, and dialkylphosphonyl;B is --Wm --Q(R2)3 or selected from 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 may also be selected from --N(R3)m H(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; each R2 is independently selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycoalkenyl 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 which is 1-methylcyclopropyl, 1-methylcyclobutyl, 1-methylcyclopentyl, or 1-methylcyclohexyl;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;
provided that B is not trimethyl when A is (diethylamino)carbonyl. - View Dependent Claims (34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63)
- and A is selected from the group consisting of --C(O)--SR3, --NH--C(X)R4, --C(═
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64. A compound of the formula ##STR5## wherein Z1 and Z2 are carbons of a furan ring;
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A is selected from the group consisting of --C(X)-amine wherein the amine is substituted with a first and a second amine substituent or with an alkylaminocarbonyl and a hydrogen, --C(O)--SR3, --NH--C(X)R4, and --C(═
NR3)--XR7 ;the first amine substituent which is selected from the group consisting of C1 -C10 straight or branched alkyl, alkenyl, or alkynyl groups or mixtures thereof substituted with one or more pyridine groups; and the second amine substituent which is selected from the group consisting of hydrogen, C1 -C6 straight or branched alkyl, alkynyl, or alkynyl groups or mixtures thereof optionally substituted with one or more halogen;
hydroxy, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, and dialkylphosphonyl;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 may also be selected from --N(R3)m H.sub.(1-m) --, --S(O)p --, and --O--;X is O or S; n is 0, 1, or 2; 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; 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 which is 1-methylcyclopropyl, 1-methylcyclobutyl, 1-methylcyclopentyl, or 1-methylcyclohexyl; 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; provided that B is not trimethylsilyl when A is (diethylamino)carbonyl or (t-butylamino)carbonyl. - View Dependent Claims (65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86)
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87. A method of controlling disease in a plant caused by Gaeumannomyces sp. comprising applying to the plant locus a composition comprising a fungicidally effective amount of a fungicide of the formula ##STR6## wherein Z1 and Z2 are C and are part of an aromatic ring which is furan;
- and
A is selected from the group consisting of --C(X)-amine wherein the amine is substituted with a first and a second amine substituent or with an alkylaminocarbonyl and a hydrogen, --C(O)--SR3, --NH--C(X)R4, and --(═
NR3)--XR7 ;the first amine substituent which is selected from the group consisting of C1 -C10 straight or branched alkyl, alkenyl, or alkynyl groups or mixtures thereof substituted with one or more pyridine groups; and the second amine substituent which is selected from the group consisting of hydrogen, C1 -C6 straight or branched alkyl, alkenyl, or alkynyl groups or mixtures thereof optionally substituted with one or more halogen;
hydroxy, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, and dialkylphosphonyl;B is --Wm --Q(R2)3 or selected from 0-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 may also be selected from --N(R3)m H(1-m)--, --S(O)p--, and --O--;X is O or S; n is 0, 1, or 2; 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; 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 which is 1-methylcyclopropyl, 1-methylcyclobutyl, 1-methylcyclopentyl, or 1-methylcyclohexyl; 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 ; provided that B is not trimethylsilyl when A is (diethylamino)carbonyl; or an agronomic salt thereof. - View Dependent Claims (88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101)
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Specification