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 --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 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, alkneyl, 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 dialylamino; and
R7 is C1-C4 alkyl, haloalkyl, or phenyl, optionally substituted with halo, nitro, or R4 ;
or an agronomic salt thereof.
1 Assignment
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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 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;
R, R2, R3, R4 and R7 are herein defined;
or an agronomic salt thereof.
49 Citations
62 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 --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; each R2 is independently selected from alkyl, alkneyl, 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 dialylamino; 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)
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33. A compound of the formula ##STR6## wherein Z1 and Z2 are carbons of a thiophene ring;
- 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 form 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) --, --N9 (R3)m H1-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, alkneyl, 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 dialylamino; 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 trimehtylsilyl when A is (diethylamino)carbonyl; and
further provided that formula I does not include ##STR7## wherein Me is methyl. - 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)
- A is selected from --C(X)-amine, --C(O)--SR3, --NH--C(X)R4, and --C(═
Specification