Fungicides for the control of take-all disease of plants

• US 6,410,558 B1
• Filed: 11/27/2000
• Issued: 06/25/2002
• Est. Priority Date: 10/18/1991
• Status: Expired due to Fees

• Current Assignee: Monsanto Technology LLC (Bayer AG)
• Original Assignee: Monsanto Technology LLC (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): Lambkin, Deborah C.
• Application Number:
  US09/722,829
• Time in Patent Office: 575 Days
• Field of Search: 548/483, 548/492, 548/503, 546/159, 546/169, 546/171, 546/176, 514/419, 514/415, 514/311, 514/313
• US Class Current: 514/311
• 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

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)_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 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 plants caused by Gaeumannomyces sp. comprising applying to the plant locus a fungicidally effective amount of a fungicide of the formula selected from:

wherein

A is selected from —

C(X)-amine, —

C(O)—

SR₃, —

NH—

C(X)R₄, and —

C(═

NR₃)—

XR₇;

X is O or S;

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;

W is —

C(R₃)_pH(<sub>2−

p</sub>)—

;

or when Q is C, W is selected from —

C(R₃)_pH(<sub>2−

p</sub>)—

,—

N(R₃)_mH(<sub>1−

m</sub>,)—

, —

S(O)_p—

, and —

O—

;

m is 0 or 1;

Q is C, Si, Ge, or Sn;

p is 0, 1, or 2;

R is 0, 1 or 2;

wherein 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, 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.

3. The method of claim 1 wherein A is —

C(O)-amine, wherein the amino radical is substituted with one or two groups selected from 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 C1-C4 alkyl, alkoxy, haloalkyl, C3-C6 cycloalkyl, halo, or nitro groups; and

C1-C4 alkyl or alkenyl substituted with pyridinyl, 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 C1-C6 alkyl groups.

4. The method of claim 3 wherein in —

W_m—

, m is 0.

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

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

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

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

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

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

11. The method of claim 10 wherein R is 1 and is methyl or halo.

12. The method of claim 3 wherein W_m is —

O— and

Q is C.

13. The method of claim 12 wherein R₂ is C1-C4 alkyl or haloalkyl.

14. The method of claim 13 wherein A is alkylaminocarbonyl or dialkylaminocarbonyl.

15. The method of claim 14 wherein A is ethylaminocarbonyl.

16. The method of claim 15 wherein R is 1 and is methyl or halo.

17. The method of claim 3 wherein W_m is —

NH—

or —

N(CH₃)— and

Q is C.

18. The method of claim 17 wherein R₂ is C1-C4 alkyl or haloalkyl.

19. The method of claim 18 wherein A is alkylaminocarbonyl or dialkylaminocarbonyl.

20. The method of claim 19 wherein A is ethylaminocarbonyl.

21. The method of claim 20 wherein R is 1 and is methyl or halo.

22. The method of claim 3 wherein B is 1-naphthyl or 2-naphthyl.

23. The method of claim 3 wherein B is 9-phenanthryl.

24. The method of claim 3 wherein B is o-tolyl.

25. The method of claim 24 wherein B is o-tolyl substituted with halogen or R₄.

26. The method of claim 24 wherein A is alkylaminocarbonyl or dialkylaminocarbonyl.

27. The method of claim 26 wherein A is ethylaminocarbonyl.

28. The method of claim 27 wherein R is 1 and is methyl or halo.

29. The method of claim 3 wherein in W_m, m is 0 and Q is C.

30. The method of claim 29 wherein R₂ is C1-C4 alkyl or haloalkyl.

31. The method of claim 30 wherein each R₂ is methyl.

32. The method of claim 31 wherein A is alkylaminocarbonyl or dialkylaminocarbonyl.

33. The method of claim 32 wherein A is ethylaminocarbonyl.

34. The method of claim 33 wherein R is 1 and is methyl or halo.

2. A compound selected from formula:

wherein

A is selected from —

C(X)-amine, —

C(O)—

SR₃, —

NH—

C(X)R₄, and —

C(═

NR₃)—

XR₇;

X is O or S;

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;

W is —

C(R₃)_pH(<sub>2−

p</sub>)—

;

or when Q is C, W is selected from —

C(R₃)_pH(<sub>2−

p</sub>)—

,—

N(R₃)_mH(<sub>1−

m</sub>,)—

, —

S(O)_p—

, and —

O—

;

m is 0 or 1;

Q is C, Si, Ge, or Sn;

p is 0, 1, or 2;

R is 0, 1 or 2;

wherein 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, 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.

35. The compound of claim 2 wherein A is —

C(O)-amine, wherein the amino radical is substituted with one or two groups selected from 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 C1-C4 alkyl, alkoxy, haloalkyl, C3-C6 cycloalkyl, halo, or nitro groups; and

C1-C4 alkyl or alkenyl substituted with pyridinyl, 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 C1-C6 alkyl groups.

36. The compound of claim 35 wherein in —

W_m—

, m is 0.

37. The compound of claim 36 wherein Q is Si.

38. The compound of claim 37 wherein each R₂ is independently selected from alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, and phenyl.

39. The compound of claim 38 wherein each R₂ is C1-C4 alkyl or haloalkyl.

40. The compound of claim 39 wherein each R₂ is methyl.

41. The compound of claim 40 wherein A is alkylaminocarbonyl or dialkylaminocarbonyl.

42. The compound of claim 41 wherein A is ethylaminocarbonyl.

43. The compound of claim 42 wherein R is 1 and is methyl or halo.

44. The compound of claim 35 wherein W_m is —

O— 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 47 wherein R is 1 and is methyl or halo.

49. The compound of claim 35 wherein W_m is —

NH—

or —

N(CH₃)— and

Q is C.

50. The compound of claim 49 wherein R₂ is C1-C4 alkyl or haloalkyl.

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

52. The compound of claim 51 wherein A is ethylaminocarbonyl.

53. The compound of claim 52 wherein R is 1 and is methyl or halo.

54. The compound of claim 35 wherein B is 1-naphthyl or 2-naphthyl.

55. The compound of claim 35 wherein B is 9-phenanthryl.

56. The compound of claim 35 wherein B is o-tolyl.

57. The compound of claim 56 wherein B is o-tolyl substituted with halogen or R₄.

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

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

60. The compound of claim 59 wherein R is 1 and is methyl or halo.

61. The compound of claim 35 wherein in W_m, m is 0 and Q is C.

62. The compound of claim 61 wherein R₂ is C1-C4 alkyl or haloalkyl.

63. The compound of claim 62 wherein each R₂ is methyl.

64. The compound of claim 63 wherein A is alkylaminocarbonyl or dialkylaminocarbonyl.

65. The compound of claim 64 wherein A is ethylaminocarbonyl.

66. The compound of claim 65 wherein R is 1 and is methyl or halo.