Fungicides for the control of take-all disease of plants

• US 6,028,101 A
• Filed: 08/07/1997
• Issued: 02/22/2000
• Est. Priority Date: 10/18/1991
• Status: Expired due to Term

• 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): Spivack, Phyllis G.
• Application Number:
  US08/908,201
• Time in Patent Office: 929 Days
• Field of Search: 514/469, 514/468, 514/470, 549/466, 549/467, 549/468, 549/471, 549/456, 549/465
• US Class Current: 514/469
• 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 and are part of an aromatic ring that is furan;

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 2;

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.

Claims

1. A method of controlling disease in a plant caused by Gaeumannomyces sp. comprising applying to the plant locus a composition comprising 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 furan;

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)--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 --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 may also be selected from --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 the two R groups are combined to form a ionheterocyclic ring fused to said furan ring which is not benzofuran when A is C(X) amine, B is W_m (Q)(R₂)₃, and Q is C or Si, said 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; and

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 alkoxy, alkylthio, alkylamino, and dialkylamino;

wherein 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 ;

provided that B is not trimethylsilyl when A is (diethylamino)carbonyl;

or an agronomic salt thereof.

2. The method of claim 1 wherein A is --C(O)--amine, wherein the first amine substituent is C₁ -C₁₀ straight or branched alkyl, alkenyl or alkynvl group, optionally substituted with one or more halogen, and the second amine substituent is hydrogen.

3. The method of claim 2 wherein in --W_m --, m is 0.

4. The method of claim 3 wherein Q is Si.

5. The method of claim 4 wherein each R₂ is independently selected from alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, and phenyl.

6. The method of claim 5 wherein each R₂ is C1-C4 alkyl or haloalkyl.

7. The method of claim 6 wherein each R₂ is methyl.

8. The method of claim 7 wherein A is alkylaminocarbonyl or dialkylaminocarbonyl.

9. The method of claim 8 wherein A is ethylaminocarbonyl.

10. The method of claim 2 wherein W_m is --O-- and Q is C.

11. The method of claim 10 wherein R₂ is C1-C4 alkyl or haloalkyl.

12. The method of claim 11 wherein A is alkylaminocarbonyl or dialkylaminocarbonyl.

13. The method of claim 12 wherein A is ethylaminocarbonyl.

14. The method of claim 2 wherein W_m is --NH-- or --N(CH₃)-- and Q is C.

15. The method of claim 14 wherein R₂ is C1-C4 alkyl or haloalkyl.

16. The method of claim 15 wherein A is alkylaminocarbonyl or dialkylaminocarbonyl.

17. The method of claim 16 wherein A is ethylaminocarbonyl.

18. The method of claim 2 wherein B is 1-naphthyl or 2-naphthyl.

19. The method of claim 2 wherein B is 9-phenanthryl.

20. The method of claim 2 wherein B is o-tolyl.

21. The method of claim 20 wherein B is o-tolyl substituted with halogen or R₄.

22. The method of claim 20 wherein A is alkylaminocarbonyl or dialkylaminocarbonyl.

23. The method of claim 22 wherein A is ethylaminocarbonyl.

24. The method of claim 2 wherein in W_m, m is 0 and Q is C.

25. The method of claim 24 wherein R₂ is C1-C4 alkyl or haloalkyl.

26. The method of claim 25 wherein each R₂ is methyl.

27. The method of claim 26 wherein A is alkylaminocarbonyl or dialkylaminocarbonyl.

28. The method of claim 27 wherein A is ethylaminocarbonyl.

29. The method of claim 1 wherein the composition also comprises an adjuvant and wherein the fungicidally effective amount of the fungicide is an amount which is effective to control Take-all.

30. A compound of the formula ##STR4## wherein Z₁ and Z₂ are carbons of a furan 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, 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 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 --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 may also be selected from --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 the two R groups are combined to form a ionheterocyclic ring fused to said furan ring which is not benzofuran when A is C(X) amine, B is W_m (Q)(R₂)₃, and Q is C or Si, said 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; and

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 alkoxy, alkylthio, alkylamino, and dialkylamino;

wherein further when Q is C 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.

31. The compound of claim 30 wherein A is --C(O)--amine, wherein the first anine substituent is C₁ -C₁₀ straight or branched alkyl, alkenyl or alkynyl group, optionally substituted with one or more halogen, and the second amine substituent is hydrogen.

32. The compound of claim 31 wherein in --W_m --, m is 0.

33. The compound of claim 32 wherein Q is Si.

34. The compound of claim 33 wherein each R₂ is independently selected from alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, and phenyl.

35. The compound of claim 34 wherein each R₂ is C1-C4 alkyl or haloalkyl.

36. The compound of claim 35 wherein each R₂ is methyl.

37. The compound of claim 36 wherein A is alkylaminocarbonyl or dialkylaminocarbonyl.

38. The compound of claim 37 wherein A is ethylaminocarbonyl.

39. The compound of claim 31 wherein W_m is --O-- and Q is C.

40. The compound of claim 39 wherein R₂ is C1-C4 alkyl or haloalkyl.

41. The compound of claim 40 wherein R₂ is methyl.

42. The compound of claim 41 wherein A is alkylaminocarbonyl or dialkylaminocarbonyl.

43. The compound of claim 42 wherein A is ethylaminocarbonyl.

44. The compound of claim 31 wherein W_m is --NH-- or --N(CH₃)-- and Q is C.

45. The compound of claim 44 wherein R₂ is C1--C4 alkyl or haloalkyl.

46. The compound of claim 45 wherein A is alkylaminocarbonyl or dialkylaminocarbonyl.

47. The compound of claim 46 wherein A is ethylaminocarbonyl.

48. The compound of claim 31 wherein B is 1-naphthyl or 2-naphthyl.

49. The compound of claim 31 wherein B is 9-phenanthryl.

50. The compound of claim 31 wherein B is o-tolyl.

51. The compound of claim 50 wherein B is o-tolyl substituted with halogen or R₄.

52. The compound of claim 50 wherein A is alkylaminocarbonyl or dialkylaminocarbonyl.

53. The compound of claim 52 wherein A is ethylaminocarbonyl.

54. The compound of claim 31 wherein in W_m, m is 0 and Q is C.

55. The compound of claim 54 wherein R₂ is C1-C4 alkyl or haloalkyl.

56. The compound of claim 55 wherein each R₂ is methyl.

57. The compound of claim 56 wherein A is alkylaminocarbonyl or dialkylaminocarbonyl.

58. The compound of claim 57 wherein A is ethylaminocarbonyl.

59. The compound of claim 31 wherein the first amine substituent is selected from the group consisting of ethyl, propyl, allyl, propargyl, isopropyl, and 2-haloethyl.

60. The compound of claim 30 wherein W is --C(R₃)_p H.sub.(2-p) -- and p is 2.