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;
- 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 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 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 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 2;
m is 0 or 1;
p is 0, 1, or 2;
wherein two R groups are combined to form a nonheterocyclic ring fused with the thiophene ring, which is not a benzothiophene other than a tetrahydrobenzothiophene, said two R groups being selected from the group consisting of C1 -C4 alkyl, alkenyl, C3 -C6 cycloalkyl and cycloalkenyl, each optionally substituted with hydroxy, thio, phenyl, C1 -C4 alkoxy, alkylthio, 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; and
further when Q is C, then two R2 groups may be combined to form a cycloalkyl 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.
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 that is thiophene;
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;
R1, R2, R3, R4 and R7 are herein defined;
or an agronomic salt thereof.
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Citations
47 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;
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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 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 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 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 2; m is 0 or 1; p is 0, 1, or 2; wherein two R groups are combined to form a nonheterocyclic ring fused with the thiophene ring, which is not a benzothiophene other than a tetrahydrobenzothiophene, said two R groups being selected from the group consisting of C1 -C4 alkyl, alkenyl, C3 -C6 cycloalkyl and cycloalkenyl, each optionally substituted with hydroxy, thio, phenyl, C1 -C4 alkoxy, alkylthio, 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; and
further when Q is C, then two R2 groups may be combined to form a cycloalkyl 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. - 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)
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25. A compound of the formula ##STR4## wherein Z1 and Z2 are C and are carbons of a thiophene 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 ;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 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 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 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 2; m is 0 or 1; p is 0, 1, or 2; wherein two R groups are combined to form a nonheterocyclic ring fused with the thiophene ring, which is not a benzothiophene other than a tetrahydrobenzothiophene, said two R groups being selected from the group consisting of C1 -C4 alkyl, alkenyl, C3 -C6 cycloalkyl and cycloalkenyl, each optionally substituted with hydroxy, thio, phenyl, C1 -C4 alkoxy, alkylthio, 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, alkyloxy, alkylthio, alkylamino, and dialkylamino;and further when Q is C then two R2 groups may be combined to form a cycloalkyl 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;
provided that B is not trimethylsilyl when A is (diethylamino)carbonyl. - View Dependent Claims (26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47)
- 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(═
Specification