US2005233905A1PendingUtilityA1
Method of improving yield and vigor of plants
Est. expiryDec 22, 2020(expired)· nominal 20-yr term from priority
Inventors:Maurice De BillotSchalk Van WykTheunis OdendaalDennis Paul PhillionJeffrey CoultasErnest SandersGrey PennerJawed AsrarMichael K. Stern
A01N 55/00
57
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Claims
Abstract
A method of improving the yield and vigor of agronomic plants, in particular leguminous plants such as soybeans, involves treating such plants and/or the propagation material of plants with a composition that includes an active agent, such as a fungicide, that has no significant activity against fungal plant pathogens of the treated plant. When the plant is not wheat, a preferred agent of this type is 4,5-dimethyl-N-(2-propenyl)-2-(trimethylsilyl)-3-thiophenecarboxamide (silthiofam). Plants and plant propagation material, such as seeds, that have been treated by the novel method are also described.
Claims
exact text as granted — not AI-modified1 - 75 . (canceled)
76 . A method of increasing the vigor and/or the yield of an agronomic plant comprising treating the plant or its propagation material with a composition which comprises an effective amount of a fungicide which has no significant activity against fungal plant pathogens for such agronomic plant.
77 . The method according to claim 77 , wherein the fungicide comprises a compound having the formula
wherein Z 1 and Z 2 are C or N and are part of an aromatic ring selected from benzene, pyridine, thiophene, furan, pyrrole, pyrazole, thiazole, benzothiophene and isothiazole;
A is selected from —C(X)-amine, —C(O)—SR 3 , —NH—C(X)R 4 , and —C(═NR 3 )—XR 7 ;
B is —W m —Q(R 2 ) 3 or selected from o-tolyl, 1-naphthyl, 2-naphthyl, and 9-phenanthryl, each optionally substituted with halogen or R 4 ;
Q is C, Si, Ge, or Sn;
W is —C(R 3 ) p H (2-p) —; or when Q is C, W is selected from —C(R 3 ) p H (2-p) —, —N(R 3 ) 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) C 1 -C 4 alkyl, alkenyl, alkynyl, C 3 -C 6 cycloalkyl, and cycloalkenyl, each optionally substituted with halo, hydroxy, thio, amino, nitro, cyano, formyl, phenyl, C 1 -C 4 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, C 1 -C 4 alkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkylamino, dialkylamino, haloalkyl, and haloalkenyl;
d) C 1 -C 4 alkoxy, alkenoxy, alkynoxy, C 3 -C 6 cycloalkyloxy, cycloalkenyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonylamino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, (alkylthio)carbonyl, phenylcarbonylamino, phenylamino, each optionally substituted with halo;
wherein two R groups may be combined to form a fused ring;
each R 2 is independently selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl and phenyl, each optionally substituted with R 4 or halogen; and wherein, when Q is C, R 2 may also be selected from halo, alkoxy, alkylthio, alkylamino, and dialkylamino;
wherein two R 2 groups may be combined to form a cyclo group with Q;
R 3 is C 1 -C 4 alkyl;
R 4 is C 1 -C 4 alkyl, haloalkyl, alkoxy, alkylthio, alkylamino, or dialkylamino;
R 7 is C 1 -C 4 alkyl, haloalkyl, or phenyl, optionally substituted with halo, nitro, or R 4 ;
or an agronomic salt thereof.
78 . The method according to claim 77 , wherein
Z 1 and Z 2 are C and are part of an aromatic ring which is thiophene; A is selected from —C(X)-amine, —C(O)—SR 3 , —NH—C(X)R 4 , and —C(═NR 3 )—XR 7 ; B is —W m —Q(R 2 ) 3 or selected from o-tolyl, 1-naphthyl, 2-naphthyl, and 9-phenanthryl, each optionally substituted with halogen or R 4 ; Q is C, Si, Ge, or Sn; W is —C(R 3 ) p H (2-p) —; or when Q is C, W is selected from —C(R 3 ) p H (2-p) —, —N(R 3 ) 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) C 1 -C 4 alkyl, alkenyl, alkynyl, C 3 -C 6 cycloalkyl, and cycloalkenyl, each optionally substituted with halo, hydroxy, thio, amino, nitro, cyano, formyl, phenyl, C 1 -C 4 alkoxy, alkylcarbonyl, alkylthio, alkylamino, dialkylamino, alkoxycarbonyl, (alkylthio)carbonyl, alkylaminocarbonyl, dialkylam inocarbonyl, alkylsulfinyl, or alkylsulfonyl; c) phenyl, furyl, thienyl, pyrrolyl, each optionally substituted with halo, formyl, cyano, amino, nitro, C 1 -C 4 alkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkylamino, dialkylamino, haloalkyl, and haloalkenyl; d) C 1 -C 4 alkoxy, alkenoxy, alkynoxy, C 3 -C 6 cycloalkyloxy, cycloalkenyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonylamino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, (alkylthio)carbonyl, phenylcarbonylamino, phenylamino, each optionally substituted with halo; each R 2 is independently selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl and phenyl, each optionally substituted with R 4 or halogen; and wherein, when Q is C, R 2 may also be selected from halo, alkoxy, alkylthio, alkylamino, and dialkylamino, and further when Q is C, R 2 may also be selected from halo, alkoxy, alkylthio, alkylamino, and dialkylamino; and further when Q is C, then two R 2 groups may be combined to form a cycloalkyl group with Q; R 3 is C 1 -C 4 alkyl; R 4 is C 1 -C 4 alkyl, haloalkyl, alkoxy, alkylthio, alkylamino, or dialkylamino; R 7 is C 1 -C 4 alkyl, haloalkyl, or phenyl, optionally substituted with halo, nitro, or R 4 ; or an agronomic salt thereof.
79 . The method according to claim 77 , wherein
Z 1 and Z 2 are C and are part of an aromatic ring which is thiophene; A is selected from —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)—SR 3 , —NH—C(X)R 4 , and —C(═NR 3 )—XR 7 ; the first amine substituent is selected from the group consisting of C 1 -C 10 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, C 3 -C 6 cycloalkyl and C 5 -C 6 cycloalkylkenyl; phenyl optionally substituted with one or more C 1 -C 4 straight or branched alkyl, alkenyl, or alkynyl groups or mixtures thereof, cycloalkyl, cycloalkenyl, haloalkyl, alkoxy and nitro; C 3 -C 6 cycloalkyl, C 5 -C 6 cycloalkenyl, alkoxy, alkenoxy, alkynoxy, dialkylamino, and alkylthio; and the second amine substituent is selected from the group consisting of hydrogen; C 1 -C 6 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 —W m —Q(R 2 ) 3 or selected from o-tolyl, 1-naphthyl, 2-naphthyl, and 9-phenanthryl, each optionally substituted with halogen or R 4 ; Q is C, Si, Ge, or Sn; W is —C(R 3 ) p H (2-p) —; or when Q is C, W is selected from —C(R 3 ) p H (2-p) —, —N(R 3 ) m H (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 C 1 -C 4 alkyl, alkenyl, C 3 -C 6 cycloalkyl and cycloalkenyl, each optionally substituted with hydroxy, thio, phenyl, C 1 -C 4 alkoxy, alkylthio, alkylsulfinyl, or alkylsufonyl; each R 2 is independently selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl and phenyl, each optionally substituted with R 4 or halogen; and wherein when Q is C, R 2 may also be selected from halo, alkoxy, alkylthio, alkylamino, and dialkylamino; and further when Q is C, then two R 2 groups may be combined to form a cycloalkyl group with Q; R 3 is C 1 -C 4 alkyl; R 4 is C 1 -C 4 alkyl, haloalkyl, alkoxy, alkylthio, alkylamino, or dialkylamino; and R 7 is C 1 -C 4 alkyl, haloalkyl, or phenyl, optionally substituted with halo, nitro, or R 4 ; or an agronomic salt thereof
80 . The method according to claim 77 , wherein
Z 1 and Z 2 are C and are part of an aromatic ring which is thiophene; A is —C(X)-amine wherein the amine is an N-bonded heterocyclic compound chosen from the group consisting of morpholine, piperazine, piperidine, and pyrrolidine, each optionally substituted with C 3 -C 6 alkyl groups; B is —W m —Q(R 2 ) 3 or selected from o-tolyl, 1-naphthyl, 2-naphthyl, and 9-phenanthryl, each optionally substituted with halogen or R 4 ; Q is C or Si; W is —C(R 3 ) p H (2-p) —; or when Q is C, W is selected from —C(R 3 ) p H (2-p) —, —N(R 3 ) m H (1-m) —, —S(O) p —, and —O—; X is O; n is 2; m is 0 or 1; p is 0, 1, or 2; wherein the two R groups are alkenyl groups and are combined to form a fused ring with the thiophene ring with is benzothiophene; wherein the alkenyl groups are optionally substituted with halo, hydroxy, thio, amino, nitro, cyano, formyl, phenyl, C 2 -C 4 alkoxy, alkylcarbonyl, alkylthio, alkylamino, dialkylamino, alkoxycarbonyl, (alkylthio)carbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylsulfinyl, or alkylsulfonyl; each R 2 is independently selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, and phenyl, each optionally substituted with R 4 or halogen; and wherein when Q is C, R 2 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; R 3 is C 1 -C 4 alkyl; and R 4 is C 1 -C 4 alkyl, haloalkyl, alkoxy, alkylthio, alkylamino, or dialkylamino; or an agronomic salt thereof
81 . The method according to claim 77 , wherein Z 1 and Z 2 are C and are part of a thiophene ring.
82 . The method according to claim 81 , wherein A is —C(O)-amine, wherein the amino radical is substituted with one or two groups selected from hydrogen; hydroxy; alkyl, alkenyl, and alkynyl, which may be straight or branched chain or cyclic; alkoxyalkyl; haloalkyl; hydroxyalkyl; alkylthio; alkylthioalkyl; alkylcarbonyl; alkoxycarbonyl; aminocarbonyl; alkylaminocarbonyl; cyanoalkyl; mono-or dialkylamino; phenyl, phenylalkyl or phenylalkenyl, each optionally substituted with one or more C 1 -C 4 alkyl, alkoxy, haloalkyl, C 3 -C 6 cycloalkyl, halo, or nitro groups; and C 1 -C 4 alkyl or alkenyl substituted with pyrimidinyl, thienyl, or furanyl; and wherein the amino radical may be a N-bonded heterocycle selected from morpholine, piperazine, piperidine, pyrrole, pyrrolidine, imidazole, and triazoles, each optionally substituted with C 1 -C 6 alkyl groups.
83 . The method according to claim 82 , wherein in —W m —, m is 0.
84 . The method according to claim 83 , wherein Q is Si.
85 . The method according to claim 84 , wherein each R 2 is C 1 -C 4 alkyl or haloalkyl.
86 . The method according to claim 85 , wherein each R 2 is methyl.
87 . The method according to claim 86 , wherein A is alkylaminocarbonyl or dialkylaminocarbonyl.
88 . The method according to claim 77 , wherein the fungicide comprises 4,5-dimethyl-N-2-propenyl-2-(trimethylsilyl)-3-thiophenecarboxamide.
89 . The method according to claim 77 , wherein
Z 1 and Z 2 are C and are part of an aromatic ring which is benzothiophene; and A is selected from —C(X)-amine wherein the amine is an unsubstituted, monosubstituted or disubstituted nonheterocyclic amino radical, —C(O)—SR 3 , —NH—C(X)R 4 , and —C(═NR 3 )—XR 7 ; B is —W m —Q(R 2 ) 3 or selected from o-tolyl, 1-naphthyl, 2-naphthyl, and 9-phenanthryl, each optionally substituted with halogen or R 4 ; Q is C, Si, Ge, or Sn; W is —C(R 3 ) p H (2-p) —; or when Q is C, W is selected from —C(R 3 ) p H (2-p) —, —N(R 3 ) 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) C 1 -C 4 alkyl, alkenyl, alkynyl, C 3 -C 6 cycloalkyl, and cycloalkenyl, each optionally substituted with halo, hydroxy, thio, amino, nitro, cyano, formyl, phenyl, C 1 -C 4 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, C 1 -C 4 alkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkylamino, dialkylamino, haloalkyl, and haloalkenyl; d) C 1 -C 4 alkoxy, alkenoxy, alkynoxy, C 3 -C 6 cycloalkyloxy, cycloalkenyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonylamino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, (alkylthio)carbonyl, phenylcarbonylamino, phenylamino, each optionally substituted with halo; each R 2 is independently selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl and phenyl, each optionally substituted with R 4 or halogen; and wherein, when Q is C, R 2 may also be selected from halo, alkoxy, alkylthio, alkylamino, and dialkylamino; wherein two R 2 groups may be combined to form a cyclo group with Q which is 1-methylcyclopropyl, 1-methylcyclopentyl, or 1-methylcyclohexyl; R 3 is C 1 -C 4 alkyl; R 4 is C 1 -C 4 alkyl, haloalkyl, alkoxy, alkylthio, alkylamino, or dialkylamino; and R 7 is C 1 -C 4 alkyl, haloalkyl, or phenyl, optionally substituted with halo, nitro, or R 4 ; or an agronomic salt thereof
90 . The method according to claim 77 , wherein
Z 1 and Z 2 are C and are part of an aromatic ring which is benzothiophene; and A is selected from —C(X)-amine wherein the amine is an unsubstituted, monosubstituted or disubstituted nonheterocyclic amino radical, —C(O)—SR 3 , —NH—C(X)R 4 , and —C(═NR 3 )—XR 7 ; B is —W m —Q(R 2 ) 3 or selected from o-tolyl, 1-naphthyl, 2-naphthyl, and 9-phenanthryl, each optionally substituted with halogen or R 4 ; Q is C, Si, Ge, or Sn; W is —C(R 3 ) p H (2-p) —; or when Q is C, W is selected from —C(R 3 ) p H (2-p) —, —N(R 3 ) 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) C 1 -C 4 alkyl, alkenyl, alkynyl, C 3 -C 6 cycloalkyl, and cycloalkenyl, each optionally substituted with halo, hydroxy, thio, amino, nitro, cyano, formyl, phenyl, C 1 -C 4 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, C 1 -C 4 alkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkylamino, dialkylamino, haloalkyl, and haloalkenyl; d) C 1 -C 4 alkoxy, alkenoxy, alkynoxy, C 3 -C 6 cycloalkyloxy, cycloalkenyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonylamino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, (alkylthio)carbonyl, phenylcarbonylamino, phenylamino, each optionally substituted with halo; each R 2 is independently selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl and phenyl, each optionally substituted with R 4 or halogen; and wherein, when Q is C, R 2 may also be selected from halo, alkoxy, alkylthio, alkylamino, and dialkylamino; wherein two R 2 groups may be combined to form a cyclo group with Q which is 1-methylcyclopropyl, 1-methylcyclopentyl, or 1-methylcyclohexyl; R 3 is C 1 -C 4 alkyl; R 4 is C 1 -C 4 alkyl, haloalkyl, alkoxy, alkylthio, alkylamino, or dialkylamino; and R 7 is C 1 -C 4 alkyl, haloalkyl, or phenyl, optionally substituted with halo, nitro, or R 4 ; or an agronomic salt thereof.
91 . The method according to claim 77 , wherein
Z 1 and Z 2 are C or N and are part of an aromatic ring which is furan; and A is selected from —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)—SR 3 , —NH—C(X)R 4 , and —C(═NR 3 )—XR 7 ; the first amine substituent is selected from the group consisting of C 1 -C 10 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, C 3 -C 6 cycloalkyl and C 5 -C 6 cycloalkylkenyl; phenyl optionally substituted with one or more C 1 -C 4 straight or branched alkyl, alkenyl, or alkynyl groups or mixtures thereof, cycloalkyl, cycloalkenyl, haloalkyl, alkoxy and nitro; C 3 -C 6 cycloalkyl, C 5 -C 6 cycloalkenyl, alkoxy, alkenoxy, alkynoxy, dialkylamino, and alkylthio; and the second amine substituent is selected from the group consisting of hydrogen; C 1 -C 6 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 —W m —Q(R 2 ) 3 or selected from o-tolyl, 1-naphthyl, 2-naphthyl, and 9-phenanthryl, each optionally substituted with halogen or R 4 ; Q is C, Si, Ge, or Sn; W is —C(R 3 ) p H (2-p) —; or when Q is C, W is selected from —C(R 3 ) p H (2-p) —, —N(R 3 ) 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) C 1 -C 4 alkyl, alkenyl, alkynyl, C 3 -C 6 cycloalkyl, and cycloalkenyl, each optionally substituted with halo, hydroxy, thio, amino, nitro, cyano, formyl, phenyl, C 1 -C 4 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, C 1 -C 4 alkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkylamino, dialkylamino, haloalkyl, and haloalkenyl; d) C 1 -C 4 alkoxy, alkenoxy, alkynoxy, C 3 -C 6 cycloalkyloxy, cycloalkenyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonylamino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, (alkylthio)carbonyl, phenylcarbonylamino, phenylamino, each optionally substituted with halo; wherein two R groups may be combined to form a fused ring; each R 2 is independently selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl and phenyl, each optionally substituted with R 4 or halogen; and wherein, when Q is C, R 2 may also be selected from halo, alkoxy, alkylthio, alkylamino, and dialkylamino; wherein two R 2 groups may be combined to form a cyclo group with Q which is 1-methylcyclopropyl, 1-methylcyclopentyl, or 1-methylcyclohexyl; R 3 is C 1 -C 4 alkyl; R 4 is C 1 -C 4 alkyl, haloalkyl, alkoxy, alkylthio, alkylamino, or dialkylamino; and R 7 is C 1 -C 4 alkyl, haloalkyl, or phenyl, optionally substituted with halo, nitro, or R 4 ; or an agronomic salt thereof
92 . The method according to claim 77 , wherein
Z 1 and Z 2 are C and are part of an aromatic ring which is furan; and A is selected from —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)—SR 3 , —NH—C(X)R 4 , and —C(═NR 3 )—XR 7 ; the first amine substituent is selected from the group consisting of C 1 -C 10 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, C 3 -C 6 cycloalkyl and C 5 -C 6 cycloalkylkenyl; phenyl optionally substituted with one or more C 1 -C 4 straight or branched alkyl, alkenyl, or alkynyl groups or mixtures thereof, cycloalkyl, cycloalkenyl, haloalkyl, alkoxy and nitro; C 3 -C 6 cycloalkyl, C 5 -C 6 cycloalkenyl, alkoxy, alkenoxy, alkynoxy, dialkylamino, and alkylthio; and the second amine substituent is selected from the group consisting of hydrogen; C 1 -C 6 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 —W m —Q(R 2 ) 3 or selected from o-tolyl, 1-naphthyl, 2-naphthyl, and 9-phenanthryl, each optionally substituted with halogen or R 4 ; Q is C, Si, Ge, or Sn; W is —C(R 3 ) p H (2-p) —; or when Q is C, W is selected from —C(R 3 ) p H (2-p) —, —N(R 3 ) 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) C 1 -C 4 alkyl, alkenyl, alkynyl, C 3 -C 6 cycloalkyl, and cycloalkenyl, each optionally substituted with halo, hydroxy, thio, amino, nitro, cyano, formyl, phenyl, C 1 -C 4 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, C 1 -C 4 alkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkylamino, dialkylamino, haloalkyl, and haloalkenyl; d) C 1 -C 4 alkoxy, alkenoxy, alkynoxy, C 3 -C 6 cycloalkyloxy, cycloalkenyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonylamino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, (alkylthio)carbonyl, phenylcarbonylamino, phenylamino, each optionally substituted with halo; wherein two R groups may be combined to form a fused ring; each R 2 is independently selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl and phenyl, each optionally substituted with R 4 or halogen; and wherein, when Q is C, R 2 may also be selected from halo, alkoxy, alkylthio, alkylamino, and dialkylamino; wherein two R 2 groups may be combined to form a cyclo group with Q which is 1-methylcyclopropyl, 1-methylcyclopentyl, or 1-methylcyclohexyl; R 3 is C 1 -C 4 alkyl; R 4 is C 1 -C 4 alkyl, haloalkyl, alkoxy, alkylthio, alkylamino, or dialkylamino; and R 7 is C 1 -C 4 alkyl, haloalkyl, or phenyl, optionally substituted with halo, nitro, or R 4 ; or an agronomic salt thereof.
93 . The method according to claim 77 , wherein
Z 1 and Z 2 are C and are part of an aromatic ring which is furan; and A is selected from —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)—SR 3 , —NH—C(X)R 4 , and —C(═NR 3 )—XR 7 ; the first amine substituent is selected from the group consisting of C 1 -C 10 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, C 3 -C 6 cycloalkyl and C 5 -C 6 cycloalkylkenyl; phenyl optionally substituted with one or more C 1 -C 4 straight or branched alkyl, alkenyl, or alkynyl groups or mixtures thereof, cycloalkyl, cycloalkenyl, haloalkyl, alkoxy and nitro; C 3 -C 6 cycloalkyl, C 5 -C 6 cycloalkenyl, alkoxy, alkenoxy, alkynoxy, dialkylamino, and alkylthio; and the second amine substituent is selected from the group consisting of hydrogen; C 1 -C 6 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 —W m —Q(R 2 ) 3 or selected from o-tolyl, 1-naphthyl, 2-naphthyl, and 9-phenanthryl, each optionally substituted with halogen or R 4 ; Q is C, Si, Ge, or Sn; W is —C(R 3 ) p H (2-p) —; or when Q is C, W is selected from —C(R 3 ) p H (2-p) —, —N(R 3 ) m H (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 the two R groups are combined to form a nonheterocyclic ring fused to said furan ring which is not benzofuran when A is —C(X)--amine, B is —Wm (Q)—(R 2 ) 3 , and Q is C or Si, said R groups being selected from the group consisting of C 1 -C 4 alkyl, alkenyl, C 3 -C 6 cycloalkyl and cycloalkenyl, each optionally substituted with hydroxy, thio, phenyl, C 1 -C 4 alkoxy, alkylthio, alkylsulfinyl, or alkylsulfonyl; and each R 2 is independently selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl and phenyl, each optionally substituted with R 4 or halogen; and wherein, when Q is C, R 2 may also be selected from halo, alkoxy, alkylthio, alkylamino, and dialkylamino; wherein further when Q is C, then two R 2 groups may be combined to form a cyclo group with Q; R 3 is C 1 -C 4 alkyl; R 4 is C 1 -C 4 alkyl, haloalkyl, alkoxy, alkylthio, alkylamino, or dialkylamino; and R 7 is C 1 -C 4 alkyl, haloalkyl, or phenyl, optionally substituted with halo, nitro, or R 4 ; or an agronomic salt thereof.
94 . The method according to claim 77 , wherein
Z 1 and Z 2 are C and are part of an aromatic ring which is pyridine; and A is selected from the group consisting of —C(O)—SR 3 , —NH—C(X)R 4 , and —C(═NR 3 )—XR 7 and —C(X)-amine wherein the amine is substituted with 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 C 1 -C 10 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, C 3 -C 6 cycloalkyl and C 5 -C 6 cycloalkylkenyl; phenyl optionally substituted with one or more C 1 -C 4 straight or branched alkyl, alkenyl, or alkynyl groups or mixtures thereof, cycloalkyl, cycloalkenyl, haloalkyl, alkoxy and nitro; C 3 -C 6 cycloalkyl, C 5 -C 6 cycloalkenyl, alkoxy, alkenoxy, alkynoxy, dialkylamino, and alkylthio; and the second amine substituent is selected from the group consisting of hydrogen; C 1 -C 6 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 —W m —Q(R 2 ) 3 or selected from o-tolyl, 1-naphthyl, 2-naphthyl, and 9-phenanthryl, each optionally substituted with halogen or R 4 ; Q is C, Si, Ge, or Sn; W is —C(R 3 ) p H (2-p) —; or when Q is C, W is selected from —C(R 3 ) p H (2-p) —, —N(R 3 ) 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) C 1 -C 4 alkyl, alkenyl, alkynyl, C 3 -C 6 cycloalkyl, and cycloalkenyl, each optionally substituted with halo, hydroxy, thio, amino, nitro, cyano, formyl, phenyl, C 1 -C 4 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, C 1 -C 4 alkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkylamino, dialkylamino, haloalkyl, and haloalkenyl; d) C 1 -C 4 alkoxy, alkenoxy, alkynoxy, C 3 -C 6 cycloalkyloxy, cycloalkenyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonylamino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, (alkylthio)carbonyl, phenylcarbonylamino, phenylamino, each optionally substituted with halo; each R 2 is independently selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl and phenyl, each optionally substituted with R 4 or halogen; and wherein, when Q is C, R 2 may also be selected from halo, alkoxy, alkylthio, alkylamino, and dialkylamino; or wherein two R 2 groups may be combined to form a cyclo group with Q which is 1-methylcyclopropyl, 1-methylcyclopentyl, or 1-methylcyclohexyl; R 3 is C 1 -C 4 alkyl; R 4 is C 1 -C 4 alkyl, haloalkyl, alkoxy, alkylthio, alkylamino, or dialkylamino; and R 7 is C 1 -C 4 alkyl, haloalkyl, or phenyl, optionally substituted with halo, nitro, or R 4 ; or an agronomic salt thereof.
95 . The method according to claim 77 , wherein
Z 1 and Z 2 are C and are part of an aromatic ring which is benzene; 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)—SR 3 , —NH—C(X)R 4 , and —C(═NR 3 )—XR 7 ; the first amine substituent is selected from the group consisting of C 1 -C 10 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, C 3 -C 6 cycloalkyl and C 5 -C 6 cycloalkylkenyl; phenyl optionally substituted with one or more C 1 -C 4 straight or branched alkyl, alkenyl, or alkynyl groups or mixtures thereof, cycloalkyl, cycloalkenyl, haloalkyl, alkoxy and nitro; C 3 -C 6 cycloalkyl, C 5 -C 6 cycloalkenyl, alkoxy, alkenoxy, alkynoxy, dialkylamino, and alkylthio; and the second amine substituent is selected from the group consisting of hydrogen; C 1 -C 6 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 —W m —Q(R 2 ) 3 or selected from o-tolyl, 1-naphthyl, 2-naphthyl, and 9-phenanthryl, each optionally substituted with halogen or R 4 ; Q is Si, Ge, or Sn; W is —C(R 3 ) p H (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) C 1 -C 4 alkyl, alkenyl, alkynyl, C 3 -C 6 cycloalkyl, and cycloalkenyl, each optionally substituted with halo, hydroxy, thio, amino, nitro, cyano, formyl, phenyl, C 1 -C 4 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, C 1 -C 4 alkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkylamino, dialkylamino, haloalkyl, and haloalkenyl; d) C 1 -C 4 alkoxy, alkenoxy, alkynoxy, C 3 -C 6 cycloalkyloxy, cycloalkenyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonylamino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, (alkylthio)carbonyl, phenylcarbonylamino, phenylamino, each optionally substituted with halo; each R 2 is independently selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl and phenyl, each optionally substituted with R 4 or halogen; R 3 is C 1 -C 4 alkyl; R 4 is C 1 -C 4 alkyl, haloalkyl, alkoxy, alkylthio, alkylamino, or dialkylamino; and R 7 is C 1 -C 4 alkyl, haloalkyl, or phenyl, optionally substituted with halo, nitro, or R 4 ; or an agronomic salt thereof.
96 . The method according to claim 76 , wherein the fungicide comprises a compound having the formula:
where A is —C(X)-amine; B is —W m —Q(R 2 ) 3 ; and A can be B when B is A except when the formula is f), then Q cannot be Si;
Q is C or Si;
W is —NH—, —O— or NCH 3 —;
X is O or S;
m is 0 or 1, provided that m is 0 when Q is Si;
n is 0, 1, 2, or 3;
p is 0, 1 or 2, and n plus p is equal to or less than 3;
each R is independently selected from
a) halo, formyl, cyano, amino, nitro, thiocyanato, isothiocyanato, trimethylsilyl, and hydroxy;
b) C 1 -C 4 alkyl, alkenyl, alkynyl, C 3 -C 6 cycloalkyl, and cycloalkenyl, each optionally substituted with halo, hydroxy, thio, amino, nitro, cyano, formyl, phenyl, C 1 -C 4 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, C 1 -C 4 alkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkylamino, dialkylamino, haloalkyl, and haloalkenyl;
d) C 1 -C 4 alkoxy, alkenoxy, alkynoxy, C 3 -C 6 cycloalkyloxy, cycloalkenyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonylamino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, (alkylthio)carbonyl, phenylcarbonylamino, phenylamino, each optionally substituted with halo; each R 2 is independently selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl and phenyl, each optionally substituted with R 4 or halogen; and wherein, when Q is C, R 2 may also be selected from halo, alkoxy, alkylthio, alkylamino, and dialkylamino; wherein two R 2 groups may be combined to form a cyclo group with Q; R 4 is C 1 -C 4 alkyl, haloalkyl, alkoxy, alkylthio, alkylamino, or dialkylamino;
or an agronomic salt thereof.
97 . The method according to claim 76 , wherein the fungicide comprises a compound having the formula:
wherein R 2 is ethyl, iso-propyl, propyl or allyl;
A is N(CH 3 ) 1-n H n R 5 or OR 6 wherein n is 0 or 1, R 5 is (CH 3 ) m (CH 3 CH 2 ) 3-m C, 1-methyl-1-cyclopentyl, 1-methyl-1-cyclohexyl or 2,3-dimethyl-2-butyl wherein m is 0, 1, 2 or 3 and R 6 is independently R 5 , or 2,3,3-trimethyl-2-butyl;
R 3 is H or independently R 4 ; and
R 4 is halo or CH 3 ;
with the proviso that when A is N(CH 3 ) 1-n H n R 5 , if R 3 is H and R 5 is 1-methyl-1-cyclohexyl or (CH 3 ) m (CH 2 CH 3 ) 3-m C, where m is 0 or 3, or if R 3 is halo and R 2 is (CH 3 ) m (CH 3 CH 2 ) 3-m C, where m is 3, then R 2 cannot be ethyl;
and with the proviso that when A is OR 6 then m is equal to or less than 2, and if R 3 is H or halo and R 2 is ethyl or isopropyl, then R 6 is (CH 3 ) M (CH 3 CH 2 ) 3-M C where m is 1;
or an agronomic salt thereof.
98 . The method according to claim 1 , wherein the agronomic plant is selected from the group consisting of corn, cereals, barley, rye, rice, vegetables, clovers, legumes, beans, peas, alfalfa, sugar cane, sugar beets, tobacco, cotton, rapeseed (canola), sunflower, safflower, and sorghum.
99 . The method according to claim 76 , wherein the agronomic plant is a member of the sub-family Papilionoideae or Faboideae.
100 . The method according to claim 99 , wherein the agronomic plant is selected from the group consisting of Pisum spp., Medicago spp., Arachis spp., Glycine spp., Vicia spp., Vigna spp., trefoil, clovers and Phaseolus spp.
101 . The method according to claim 99 , wherein the agronomic plant is a soybean plant.
102 . The method according to claim 101 , where the treatment comprises treatment of the seed of the soybean plant with an inoculant comprising Azospirillium spp., or Rhizobium spp., or Bradyrhizobium spp., or a mixture of Rhizobium spp. and Bradyrhizobium spp., or a mixture of either Rhizobium spp., or Bradyrhizobium spp. with any other microorganisms.
103 . The method according to claim 76 , wherein the step of treating the plant or its propagation material comprises treating the seed with an effective amount of the fungicide.
104 . The method according to claim 76 , wherein the step of treating the plant or its propagation material comprises applying the fungicide to the foliage of the plant.
105 . The method according to claim 103 , wherein the agronomic plant is selected from the group consisting of Pisum spp., Medicago spp., Arachis spp., Glycine spp., Vicia spp., Vigna spp., trefoil, clovers and Phaseolus spp.
106 . The method according to claim 103 , wherein the seed is treated with an inoculant comprising Azospirillium spp., or Rhizobium spp., or Bradyrhizobium spp., or a mixture of Rhizobium spp. and Bradyrhizobium spp., or a mixture of either Rhizobium spp., or Bradyrhizobium spp. with any other microorganisms.
107 . The method according to claim 103 , wherein the seed is treated with an inoculant comprising Bradyrhizobium japonicum.
108 . The method according to claim 103 , wherein the seed is treated with an amount of the composition sufficient to include the fungicide in an amount that is within the range of about 0.1 gm/100 kg of seed to about 500 gm/100 kg of seed.
109 . The method according to claim 103 , wherein the seed is treated with an amount of the composition sufficient to include the fungicide in an amount that is within the range of about 10 gm/100 kg of seed to about 100 gm/100 kg of seed.
110 . The method according to claim 103 , wherein the seed is treated with an amount of the composition sufficient to include the fungicide in an amount that is within the range of about 20 gm/100 kg of seed to about 50 gm/100 kg of seed.
111 . The method according to claim 76 , wherein the seed possesses a transgenic event providing the plant with resistance to a herbicide and the treatment comprises foliar application of said herbicide.
112 . The method according to claim 111 , wherein the herbicide is selected from the group consisting of glyphosate, glyphosinate, imidazilinone and STS system.
113 . The method according to claim 103 , wherein the seed possesses a transgenic event providing the plant with resistance to a herbicide selected from the group consisting of glyphosate, glyphosinate, imidazilinone and STS system and the treatment comprises foliar application of said herbicide.
114 . The method according to claim 76 , wherein the treatment comprises treating the seed of the plant with an inoculant selected from the group consisting of Azospirillium spp., Rhizobium spp., Bradyrhizobium spp., a mixture of Rhizobium spp. and Bradyrhizobium spp., and a mixture of either Rhizobium spp., or Bradyrhizobium spp. with any other microorganisms, and further includes foliar treatment of the plant with a compound having the formula
wherein Z 1 and Z 2 are C or N and are part of an aromatic ring selected from benzene, pyridine, thiophene, furan, pyrrole, pyrazole, thiazole, benzothiophene and isothiazole;
A is selected from —C(X)-amine, —C(O)—SR 3 , —NH—C(X)R 4 , and —C(═NR 3 )—XR 7 ;
B is —W m —Q(R 2 ) 3 or selected from o-tolyl, 1-naphthyl, 2-naphthyl, and 9-phenanthryl, each optionally substituted with halogen or R 4 ;
Q is C, Si, Ge, or Sn;
W is —C(R 3 ) p H (2-p) —; or when Q is C, W is selected from —C(R 3 ) p H (2-p) —, —N(R 3 ) 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) C 1 -C 4 alkyl, alkenyl, alkynyl, C 3 -C 6 cycloalkyl, and cycloalkenyl, each optionally substituted with halo, hydroxy, thio, amino, nitro, cyano, formyl, phenyl, C 1 -C 4 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, C 1 -C 4 alkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkylamino, dialkylamino, haloalkyl, and haloalkenyl;
d) C 1 -C 4 alkoxy, alkenoxy, alkynoxy, C 3 -C 6 cycloalkyloxy, cycloalkenyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonylamino, aminocarbonyl, alkylaminocarbonyl, dialkylam inocarbonyl, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, (alkylthio)carbonyl, phenylcarbonylamino, phenylamino, each optionally substituted with halo;
wherein two R groups may be combined to form a fused ring;
each R 2 is independently selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl and phenyl, each optionally substituted with R 4 or halogen; and wherein, when Q is C, R 2 may also be selected from halo, alkoxy, alkylthio, alkylamino, and dialkylamino;
wherein two R 2 groups may be combined to form a cyclo group with Q;
R 3 is C 1 -C 4 alkyl;
R 4 is C 1 -C 4 alkyl, haloalkyl, alkoxy, alkylthio, alkylamino, or dialkylamino; and
R 7 is C 1 -C 4 alkyl, haloalkyl, or phenyl, optionally substituted with halo, nitro, or R 4 ;
or an agronomic salt thereof.
115 . The method according to claim 114 , wherein the seed possesses a transgenic event providing the plant with resistance to a herbicide selected from the group consisting of glyphosate, glyphosinate, imidazilinone and STS system and the treatment further comprises foliar application of said herbicide.
116 . The method according to claim 103 , wherein the seed possesses a transgenic event providing the plant with resistance to a herbicide and the step of applying the fungicide to the foliage of the plant comprises the application of the fungicide in combination with said herbicide.
117 . The method according to claim 116 , wherein the herbicide is glyphosate.
118 . A method of increasing the vigor and/or the yield of an agronomic plant except for wheat comprising treating an agronomic plant or its propagation material except for wheat with a composition comprising an effective amount of an active agent that has activity against Gaeumannomyces graminis.
119 . The method according to claim 118 , wherein the active agent comprises a compound having the formula
wherein Z 1 and Z 2 are C or N and are part of an aromatic ring selected from benzene, pyridine, thiophene, furan, pyrrole, pyrazole, thiazole, benzothiophene and isothiazole;
A is selected from —C(X)-amine, —C(O)—SR 3 , —NH—C(X)R 4 , and —C(═NR 3 )—XR 7 ;
B is —W m —Q(R 2 ) 3 or selected from o-tolyl, 1-naphthyl, 2-naphthyl, and 9-phenanthryl, each optionally substituted with halogen or R 4 ;
Q is C, Si, Ge, or Sn;
W is —C(R 3 ) p H (2-p) —; or when Q is C, W is selected from —C(R 3 ) p H (2-p) —, —N(R 3 ) 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) C 1 -C 4 alkyl, alkenyl, alkynyl, C 3 -C 6 cycloalkyl, and cycloalkenyl, each optionally substituted with halo, hydroxy, thio, amino, nitro, cyano, formyl, phenyl, C 1 -C 4 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, C 1 -C 4 alkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkylamino, dialkylamino, haloalkyl, and haloalkenyl;
d) C 1 -C 4 alkoxy, alkenoxy, alkynoxy, C 3 -C 6 cycloalkyloxy, cycloalkenyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonylamino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, (alkylthio)carbonyl, phenylcarbonylamino, phenylamino, each optionally substituted with halo;
wherein two R groups may be combined to form a fused ring;
each R 2 is independently selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl and phenyl, each optionally substituted with R 4 or halogen; and wherein, when Q is C, R 2 may also be selected from halo, alkoxy, alkylthio, alkylamino, and dialkylamino; wherein two R 2 groups may be combined to form a cyclo group with Q;
R 3 is C 1 -C 4 alkyl; and
R 4 is C 1 -C 4 alkyl, haloalkyl, alkoxy, alkylthio, alkylamino, or dialkylamino;
R 7 is C 1 -C 4 alkyl, haloalkyl, or phenyl, optionally substituted with halo, nitro, or R 4 ;
or an agronomic salt thereof.
120 . The method according to claim 119 , wherein the active agent comprises 4,5-dimethyl-N-2-propenyl-2-(trimethylsilyl)-3-thiophenecarboxamide.
121 . The method according to claim 118 , where the treatment further comprises treatment of the seed with an inoculant comprising Azospirillium spp., or Rhizobium spp., or Bradyrhizobium spp., or a mixture of Rhizobium spp. and Bradyrhizobium spp., or a mixture of either Rhizobium spp., or Bradyrhizobium spp. with any other microorganisms.
122 . The method according to claim 119 , wherein the plant or its propagation material comprises a seed which possesses a transgenic event providing the plant with resistance to a herbicide and the treatment comprises foliar application of said herbicide.
123 . The method according to claim 122 , wherein the herbicide is selected from the group consisting of glyphosate, glyphosinate, imidazilinone and STS system.
124 . The method according to claim 118 , wherein the treatment comprises treating the seed of the plant with an inoculant selected from the group consisting of Azospirillium spp., Rhizobium spp., Bradyrhizobium spp., a mixture of Rhizobium spp. and Bradyrhizobium spp., and a mixture of either Rhizobium spp., or Bradyrhizobium spp. with any other microorganisms, and further includes foliar treatment of the plant with the fungicide.
125 . The method according to claim 124 , wherein the herbicide is glyphosate.
126 . An agronomic plant or its propagation material for which Gaeumannomyces graminis is not a disease-causing organism, wherein the plant or its propagation material has been treated with a composition comprising an effective amount of an active agent which has activity against Gaeumannomyces graminis, and wherein the plant is not wheat.
127 . A plant or its propagation material which has been treated with a composition comprising a fungicide in an amount sufficient to increase the yield and/or the vigor of the plant, wherein the fungicide is one having no significant activity against fungal plant pathogens of said plant or its propagation material.
128 . The plant or its propagation material according to claim 127 , wherein the plant is a soybean plant or its seed which has been treated with a composition comprising 4,5-dimethyl-N-(2-propenyl)-2-(trimethylsilyl)-3-thiophenecarboxamide.
129 . The plant or its propagation material according to claim 128 , wherein the soybean seed is contacted with an inoculant comprising Rhizobium spp., or Bradyrhizobium spp., or a mixture of Rhizobium spp. and Bradyrhizobium spp., or a mixture of either Rhizobium spp., or Bradyrhizobium spp. with any other microorganisms.
130 . The plant or its propagation material according to claim 129 , wherein the plant or its propagation material has a transgenic event.
131 . A seed that has been treated by the method of claim 76 .
132 . A method for increasing the vigor and/or the yield of an agronomic plant or its propagation material comprising treating the seed and/or the foliage of such plant with a compound having the formula:
wherein Z 1 and Z 2 are C or N and are part of an aromatic ring selected from benzene, pyridine, thiophene, furan, pyrrole, pyrazole, thiazole, benzothiophene and isothiazole;
A is selected from —C(X)-amine, —C(O)—SR 3 , —NH—C(X)R 4 , and —C(═NR 3 )—XR 7 ;
B is —W m —Q(R 2 ) 3 or selected from o-tolyl, 1-naphthyl, 2-naphthyl, and 9-phenanthryl, each optionally substituted with halogen or R 4 ;
Q is C, Si, Ge, or Sn;
W is —C(R 3 ) p H (2-p) —; or when Q is C, W is selected from —C(R 3 ) p H (2-p) —, —N(R 3 ) 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) C 1 -C 4 alkyl, alkenyl, alkynyl, C 3 -C 6 cycloalkyl, and cycloalkenyl, each optionally substituted with halo, hydroxy, thio, amino, nitro, cyano, formyl, phenyl, C 1 -C 4 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, C 1 -C 4 alkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkylamino, dialkylamino, haloalkyl, and haloalkenyl;
d) C 1 -C 4 alkoxy, alkenoxy, alkynoxy, C 3 -C 6 cycloalkyloxy, cycloalkenyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonylamino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, (alkylthio)carbonyl, phenylcarbonylamino, phenylamino, each optionally substituted with halo;
wherein two R groups may be combined to form a fused ring;
each R 2 is independently selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl and phenyl, each optionally substituted with R 4 or halogen; and wherein, when Q is C, R 2 may also be selected from halo, alkoxy, alkylthio, alkylamino, and dialkylamino; wherein two R 2 groups may be combined to form a cyclo group with Q;
R 3 is C 1 -C 4 alkyl;
R 4 is C 1 -C 4 alkyl, haloalkyl, alkoxy, alkylthio, alkylamino, or dialkylamino; and
R 7 is C 1 -C 4 alkyl, haloalkyl, or phenyl, optionally substituted with halo, nitro, or R 4 ;
or an agronomic salt thereof;
except that the agronomic plant is not wheat when the compound is silthiofam.
133 . A method for increasing the vigor and/or the yield of an agronomic plant or its propagation material comprising treating the seed and/or the foliage of such plant with a compound having the formula:
where A is —C(X)-amine; B is —W m —Q(R 2 ) 3 ; and A can be B when B is A except when the formula is f), then Q cannot be Si;
Q is C or Si;
W is —NH—, —O— or NCH 3 —;
X is O or S;
m is 0 or 1, provided that m is 0 when Q is Si;
n is 0, 1, 2, or 3;
p is 0, 1 or 2, and n plus p is equal to or less than 3;
each R is independently selected from
a) halo, formyl, cyano, amino, nitro, thiocyanato, isothiocyanato, trimethylsilyl, and hydroxy;
b) C 1 -C 4 alkyl, alkenyl, alkynyl, C 3 -C 6 cycloalkyl, and cycloalkenyl, each optionally substituted with halo, hydroxy, thio, amino, nitro, cyano, formyl, phenyl, C 1 -C 4 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, C 1 -C 4 alkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkylamino, dialkylamino, haloalkyl, and haloalkenyl;
d) C 1 -C 4 alkoxy, alkenoxy, alkynoxy, C 3 -C 6 cycloalkyloxy, cycloalkenyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonylamino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, (alkylthio)carbonyl, phenylcarbonylamino, phenylamino, each optionally substituted with halo; each R 2 is independently selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl and phenyl, each optionally substituted with R 4 or halogen; and wherein, when Q is C, R 2 may also be selected from halo, alkoxy, alkylthio, alkylamino, and dialkylamino; wherein two R 2 groups may be combined to form a cyclo group with Q; R 4 is C 1 -C 4 alkyl, haloalkyl, alkoxy, alkylthio, alkylamino, or dialkylamino;
or an agronomic salt thereof.
134 . A method for increasing the vigor and/or the yield of an agronomic plant or its propagation material comprising treating the seed and/or the foliage of such plant with a compound having the formula:
wherein R 2 is ethyl, iso-propyl, propyl or allyl;
A is N(CH 3 ) 1-n H n R 5 or OR 6 wherein n is 0 or 1, R 5 is (CH 3 ) m (CH 3 CH 2 ) 3-m C, 1-methyl-1-cyclopentyl, 1-methyl-1-cyclohexyl or 2,3-dimethyl-2-butyl wherein m is 0, 1, 2 or 3 and R 6 is independently R 5 , or 2,3,3-trimethyl-2-butyl;
R 3 is H or independently R 4 ; and
R 4 is halo or CH 3 ;
with the proviso that when A is N(CH 3 ) 1-n H n R 5 , if R 3 is H and R 5 is 1-methyl-1-cyclohexyl or (CH 3 ) m (CH 2 CH 3 ) 3-m C, where m is 0 or 3, or if R 3 is halo and R 2 is (CH 3 ) m (CH 3 CH 2 ) 3-m C, where m is 3, then R 2 cannot be ethyl;
and with the proviso that when A is OR 6 then m is equal to or less than 2, and if R 3 is H or halo and R 2 is ethyl or isopropyl, then R 6 is (CH 3 ) M (CH 3 CH 2 ) 3-M C where m is 1;
or an agronomic salt thereof.
135 . A method for increasing the vigor and/or the yield of an agronomic plant or its propagation material except for wheat comprising treating the seed and/or the foliage of such plant with silthiofam.Cited by (0)
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