Fungicides for the control of take-all disease of plants

• US 5,834,447 A
• Filed: 12/08/1995
• Issued: 11/10/1998
• Est. Priority Date: 10/18/1991
• Status: Expired due to Fees

• Current Assignee: Monsanto Technology LLC (Bayer AG)
• Original Assignee: Monsanto Company (Bayer AG)
• Inventors: Phillion, Dennis Paul, Phillips, Wendell Gary, Braccolino, Diane Susan, Van Sant, Karey Alan, Walker, Daniel Mark, Graneto, Matthew James, Wong, Sai Chi
• Primary Examiner(s): Rotman, Alan L.
• Application Number:
  US08/569,273
• Time in Patent Office: 1,068 Days
• Field of Search: 546/14, 546/213, 544/153, 544/376, 544/146, 544/374, 548/406, 548/517, 548/527, 514/63, 514/324, 514/326, 514/422, 514/231.5, 514/233.5
• US Class Current: 514/63
• CPC Class Codes: A01N 37/18 containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
• CPC Class Codes: A01N 37/26 containing the group; Thio analogues thereof
• CPC Class Codes: A01N 37/40 having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
• CPC Class Codes: A01N 37/44 containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
• CPC Class Codes: A01N 41/10 Sulfones; Sulfoxides
• CPC Class Codes: A01N 55/00 Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur containing organo-phosphorus compounds A01N57/00
• CPC Class Codes: A01N 55/02 containing metal atoms
• CPC Class Codes: A01N 55/04 Tin
• CPC Class Codes: C07C 233/65 having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
• CPC Class Codes: C07C 233/66 having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
• CPC Class Codes: C07C 233/69 of an acyclic saturated carbon skeleton
• CPC Class Codes: C07C 235/60 having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
• CPC Class Codes: C07C 237/30 having the nitrogen atom of the carboxamide group bound to hydrogen atoms or to acyclic carbon atoms
• CPC Class Codes: C07C 2601/04 with a four-membered ring
• CPC Class Codes: C07C 2601/08 the ring being saturated
• CPC Class Codes: C07C 317/44 having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
• CPC Class Codes: C07C 323/60 with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
• CPC Class Codes: C07F 15/025 without a metal-carbon linkage
• CPC Class Codes: C07F 7/081 comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
• CPC Class Codes: C07F 7/0812 comprising a heterocyclic ring
• CPC Class Codes: C07F 7/0814 : said ring is substituted at a C ring atom by Si
• CPC Class Codes: C07F 7/2208 : Compounds having tin linked only to carbon, hydrogen and/or halogen
• CPC Class Codes: C07F 7/30 : Germanium compounds

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 selected from benzene, pyridine, thiophene, furan, pyrrole, pyrazole, thiazole, and isothiazole;

A is selected from --C(X)--amine, --C(O)--SR₃, --NH--C(X)R₄, and --C(═NR₃)--XR₇ ;

B is --W_m --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;

wherein two R groups may be combined to form a fused ring;

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;

wherein two R₂ groups may be 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 thereof.

Claims

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;

and

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 C₁ -C₆ alkyl groups;

B is --W_m Q(R₂)₃ ;

or selected from o-tolyl, 1-naphthyl, 2-naphthyl, and 9-phenantbryl, each optionally substituted with halogen or R₄ ;

Q is C or Si,

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;

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 which is benzothiophene;

wherein the alkenyl groups are 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;

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;

or wherein two R₂ groups may be combined to form a cyclo group with Q;

R₃ is C₁ -C₄ alkyl;

R₄ is C₁ -C₄ alkyl, haloalkyl, alkoxy, alkylthio, alkylamino, or dialkylamino;

or an agronomic salt thereof.

3. A fungicidal composition comprising an effective amount of the compound of claim 1 and an agronomically acceptable carrier.

4. A method of claim 1 wherein in --W_m --, m is zero.

5. A method of claim 4 wherein Q is Si.

6. A method of claim 5 wherein each R₂ is independently selected from alkyl, alkenyl, alknyl, cycloalkyl, haloalkyl, and phenyl.

7. A method of claim 6 wherein each R₂ is C₁ -C₄ or alkyl or haloalkyl.

8. A method of claim 7 wherein each R₂ is methyl.

9. A method of claim 1 wherein W_m is --O-- and Q is C.

10. A method of claim 9 wherein R₂ is C₁ -C₄ alkyl or haloalkyl.

11. A method of claim 1 wherein W_m is --NH-- or --N(CH₃)-- and Q is C.

12. A method of claim 11 wherein R₂ is C₁ -C₄ alkyl or cycloalkyl.

13. A compound of claim 12 wherein in --W_m --, m is zero.

14. A compound of claim 13 wherein Q is Si.

15. A compound of claim 14 wherein each R₂ is independently selected from alkyl, alkenyl, alknyl, cycloalkyl, haloalkyl, and phenyl.

16. A compound of claim 15 wherein each R₂ is C₁ -C₄ alkyl or haloalkyl.

17. A compound of claim 16 wherein each R₂ is methyl.

18. A compound of claim 17 wherein W_m is --O--, and Q is C.

19. A compound of claim 18 wherein R₂ is C₁ -C₄ alkyl or haloalkyl.

20. A compound of claim 19 wherein W_m is --NH-- or --N(CH₃)-- and Q is C.

21. A compound of claim 20 wherein R₂ is C₁ -C₄ alkyl or cycloalkyl.

26. A compound of claim 1 wherein m is O and Q is C.

27. A compound of claim 26 wherein R₂ is C₁ -C₄ alkyl or haloalkyl.

2. A compound of the formula ##STR4## wherein Z₁ and Z₂ are C and are part of an aromatic ring which is thiophene;

and

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 C₁ -C₆ alkyl groups;

B is --W_m 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 or Si,

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;

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 which is benzothiophene;

wherein the alkenyl groups are 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;

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;

or wherein two R₂ groups may be combined to form a cyclo group with Q;

or an agronomic salt thereof.

22. A compound of claim 2 wherein B is 1-naphthyl or 2-naphthyl.

23. A compound of claim 2 wherein B is 9-phenanthryl.

24. A compound of claim 2 wherein B is 0-tolyl.

25. A compound of claim 24 wherein B is 0-tolyl substituted with halogen or R₄.