Fungicides for the control of take-all disease of plants
First Claim
Patent Images
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:
-
wherein 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, 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 dialkyl-phosphonyl;
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)pH(2−
p)—
;
or when Q is C, W is selected from —
C(R3)pH(2−
p)—
, —
N(R3)mH(1−
m)—
, —
S(O)p—
, and —
O—
;
X is 0 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 is selected from the group consisting of alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl alkoxy, alkyloxy, alkylthio, alkylamino, dialkylamino and phenyl, each optionally substituted with R4 or halogen;
or, wherein two R2 groups as defined above are 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 forming cation;
R is 0, 1, 2 or 3 and each R is independently selected from a) formyl, amino, 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, alkylsufinyl, 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;
or 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; and
wherein two R groups optionally combine to form a fused benzene ring with the pyrrole ring.
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Abstract
A method of controlling Take-all disease of plants by applying, preferably to the seed prior to planting, a fungicide of the formula
33 Citations
49 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:
-
wherein 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, 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 dialkyl-phosphonyl;
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)pH(2−
p)—
;
or when Q is C, W is selected from —
C(R3)pH(2−
p)—
, —
N(R3)mH(1−
m)—
, —
S(O)p—
, and —
O—
;
X is 0 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 is selected from the group consisting of alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl alkoxy, alkyloxy, alkylthio, alkylamino, dialkylamino and phenyl, each optionally substituted with R4 or halogen;
or,wherein two R2 groups as defined above are 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 forming cation;
R is 0, 1, 2 or 3 and each R is independently selected from a) formyl, amino, 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, alkylsufinyl, 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;
ord) 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; and
wherein two R groups optionally combine to form a fused benzene ring with the pyrrole ring. - View Dependent Claims (3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26)
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-
2. A compound of the formula:
-
wherein 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, 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 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)pH(2−
p)—
;
or when Q is C, W is selected from —
C(R3)pH(2−
p)—
, —
N(R3)mH(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 is selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl and phenyl, each optionally substituted with R4 or halogen;
orwherein two R2 groups as defined above are combined to form a cyclo group with Q;
R3 is C1-C4 alkyl;
R4 is C1-C4 alkyl, haloalkyl, alkoxy, alkylthio, alkylamino, or dialkylamino;
R7 is C1-C4 alkyl, haloalkyl, or phenyl, optionally substituted with halo, nitro, or R4;
or an agronomic salt forming cation;
R is 0, 1, 2 or 3 and each R is independently selected from;
a) formyl, amino, 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, alkylsufinyl, 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;
ord) 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; and
wherein two R groups optionally combine to form a fused benzene ring with the pyrrole ring. - View Dependent Claims (27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49)
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Specification