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 benzene;
- 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 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, 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 o-tolyl, 1-naphthyl, 2-naphthyl, and 9-phenanthryl, each optionally substituted with halogen or R4 ;
Q is Si, Ge, or Sn;
W is --C(R3)p H.sub.(2-p) --;
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;
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 and method for controlling Take-all disease of plants are disclosed by applying a fungicide of the formula: ##STR1## wherein Z1 and Z2 are carbons of a benzene ring; 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 ;
B is --Wm --Q(R2)3 ; Q is Si, Ge, or Sn; W is --C(R3)p H.sub.(2-p) --; n is 0, 1, 2, or 3; m is 0 or 1; p is 0, 1, or 2;
or an agronomic salt thereof;
the first and second amine substituents and R, R2, R3, R4, and R7 are defined herein.
45 Citations
35 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 benzene;
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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 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, 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 o-tolyl, 1-naphthyl, 2-naphthyl, and 9-phenanthryl, each optionally substituted with halogen or R4 ; Q is Si, Ge, or Sn; W is --C(R3)p H.sub.(2-p) --; 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; 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)
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19. A compound of the formula ##STR4## wherein Z1 and Z2 are part of a benzene ring;
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A is selected from --C(X)-amine, wherein the amine is substituted with a first and 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 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, 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 o-tolyl, 1-naphthyl, 2-naphthyl, and 9-phenanthryl, each optionally substituted with halogen or R4 ; Q is Si, Ge, or Sn; W is --C(R3)p H.sub.(2-p) --; 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; 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 n is not zero when B is trimethylsilyl and A is N,N-diethylaminocarbonyl, N,N-bis(1-methylethyl)aminocarbonyl, N-methylaminothiocarbonyl, N-ethylaminocarbonyl, or N-phenylamninocarbonyl; and further providing that when B is trimethylsilyl and A is N-methylaminothiocarbonyl, n is not zero, then R is not 4-chloro or 4-methoxy; further providing that when B is trimethylsilyl and A is N-ethylaminocarbonyl, n is not zero and R is not 3-OH or when B is ortho-tolyl and A is N,N-diethylaminocarbonyl, N,N-bis(1-methylethyl)aminocarbonyl, N-methylaminocarbonyl, or O-methylcarbamyl, n is not zero;
or when B is trimethylstannyl and A is N,N-diethylaminocarbonyl or O-(1,1-dimethylethyl)carbamyl, n is not zero;and further provided that when B is 2-trimethylsilyl and A is N,N-diethylaminocarbonyl, n is not zero and R is not 3-fluoro-6-formyl, 3-fluoro-6-methyl, 3-chloro-6-formyl, 3-fluoro, 3-chloro, 3-chloro-6-methyl, 6-trimethylsilyl, or 6-methyl 4-fluoro 4-fluoro-5-TMS 5-OMe-6-OMe 3-n-Bu 3-phenyl 3-Me-4-Me-6-OMe 3-OMe-4-OMe 3-OMe 6-OMe 3-OMe-6-Me 3-OMe-6-formyl 3-OMe-4-OMe-6-Me 3-OMe-6-S Me 3-OMe-6-I 3-OMe-6-(C═
O)NEt23-OMe-5-(C═
O)NEt2 -6-(C═
O)NEt23-OMe-6-TMS 3-OMe-4-OMe-6-formyl 3-Br-6-OMe 3-OMe-4-OMe-6-Br 3-OMe-4-CHMeOMe-6-OMe ##STR5## 3-OH 6-OH 5-OH 4-OH 3-OH-6-TMS 4-OH-6-TMS 3-OMe-6-OH 3-OMe-6-NH2 5-TMS-6-Et2 NCO 6-Et2 NCO; and further provided that when A is O-(1,2-dimethylethyl)carbamyl and B is 2-trimethylsilyl, R is not 5-trifluoromethyl; and further provided that when A is diethylaminocarbonyl and B is triethylsilyl, R is not 6-OH; and further provided that when A is phenylaminocarbonyl and B is trimethylsilyl, R is not 6-Cl, 3-Cl, or 4-Cl; and further provided that when A is methylaminocarbonyl and B is trimethylsilyl, R is not 5,6-dimethoxy; and further provided that when A is t-butylaminocarbonyl and B is trimethylstannyl, R is not 3-MeO-5-Me; and further provided that when A is N-methylaminocarbonyl and B is trimethylsilylmethyl, n is not zero; and further provided that when A is N,N-diethylaminocarbonyl and B is 1-(trimethylsilyl)ethyl, n is not zero; and further provided that when A is N,N-diethylaminocarbonyl and B is trimethylsilylmethyl, n is not zero and R is not 3-TMS 6-OMe 3-Cl 3-OMe; and further provided that when A is N,N-diisopropylaminocarbonyl and B is trimethylsilylmethyl, n is not zero; and further provided that when A is N,N-diethylaminocarbonyl and B is 6-methylphenyl, n is not zero and R is not 3-OMe 6-OMe, 6-(2-methylphenyl and further provided that when A is O-methylcarbamyl and B is trimethylsilylmethyl, R is not 4-OMe or 4-phenyl; and further provided that when A is t-butylcarbonylamino and B is trimethylsilylmethyl, n is not zero; and further provided that when A is methylcarbonylamino and B is trimethylsilylmethyl, n is not zero; and further provided that when A is methylcarbonylamino and B is trimethylsilyl, n is not zero and R is not 4-NMe2 ; and further provided that when A is methylcarbonylamino and B is triethylsityl, R is not 4-Me; and further provided that when A is O-(t-butyl)carbamyl and B is trimethylstannyl, n is not zero and R is not 3-Cl-5-Cl 3-Br-5-F 3-OCH2 OMe-5-Me; and further provided that when A is trifluoromethylcarbonylamino and B is trimethylstannyl, n is not zero; and further provided that when A is methylaminocarbonyl and B is 2-napthyl, n is not zero; and further provided that when A is diethylaminocarbonyl and B is 9-phenanthryl, n is not zero. - View Dependent Claims (20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35)
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Specification