Fungicides for the control of take-all disease of plants

• US 5,693,667 A
• Filed: 12/28/1994
• Issued: 12/02/1997
• 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:
  US08/365,391
• Time in Patent Office: 1,070 Days
• Field of Search: 514/461, 514/184, 514/422, 514/444, 514/471, 514/472, 514/473, 549/206, 549/214, 549/474, 549/475, 549/476, 549/478, 549/479, 549/480, 549/481, 549/482, 549/483, 549/484, 549/3, 549/4, 549/60
• US Class Current: 514/461
• 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 compound, composition, and method for controlling Take-all disease of plants by applying a fungicide of the formula: ##STR1## 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 ;

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 0, 1, or 2; m is 0 or 1; p is 0, 1, or 2;

wherein two R₂ groups may be combined to form a cyclo group with Q which is 1-methylcyclopropyl, 1-methylcyclobutyl, 1-methylcyclopentyl, or 1-methylcyclohexyl;

provided that B is not trimethylsilyl when A is (diethylamino)carbonyl or (t-butylamino)carbonyl;

or an agronomic salt thereof;

the first and second amine substituents and R, R₂, R₃, R₄, and R₇ are defined herein.

Claims

1. A compound of the formula ##STR3## 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 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 0, 1, or 2;

m is 0 or 1;

p is0, 1, or2;

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 which is 1-methylcyclopropyl, 1-methylcyclobutyl, 1-methylcyclopentyl, or 1-methylcyclohexyl;

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 or (t-butylamino)carbonyl.

2. The compound of claim 1 wherein A is --C(O)-amine, wherein the first amine substituent is a C₂ -C₆ straight or branched alkyl or alkenyl group optionally substituted with one or more halogen and second amine substituent is hydrogen.

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

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

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

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

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

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

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

10. The compound of claim 9 wherein in R_n, n is 1 and R is methyl or halo.

11. The compound of claim 10 wherein R₂ is methyl.

12. The compound of claim 2 wherein W_m is --O-- and Q is C.

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

14. The compound of claim 13 wherein R₂ is methyl.

15. The compound of claim 14 wherein A is alkylaminocarbonyl or dialkylaminocarbonyl.

16. The compound of claim 15 wherein A is ethylaminocarbonyl.

17. The compound of claim 16 wherein in R_n, n is 1 and R is methyl or halo.

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

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

20. The compound of claim 19 wherein A is alkylaminocarbonyl or dialkylaminocarbonyl.

21. The compound of claim 20 wherein A is ethylaminocarbonyl.

22. The compound of claim 21 wherein in R_n, n is 1 and R is methyl or halo.

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

24. The compound of claim 2 wherein B is 9-phenanthryl.

25. The compound of claim 2 wherein B is o-tolyl.

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

27. The compound of claim 25 wherein A is alkylaminocarbonyl or dialkylaminocarbonyl.

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

29. The compound of claim 28 wherein in R_n, n is 1 and R is methyl or halo.

30. The compound of claim 2 wherein in W_m, m is 0 and Q is C.

31. The compound of claim 30 wherein R₂ is C1-C4 alkyl or haloalkyl.

32. The compound of claim 31 wherein each R₂ is methyl.

33. The compound of claim 32 wherein A is alkylaminocarbonyl or dialkylaminocarbonyl.

34. The compound of claim 33 wherein A is ethylaminocarbonyl.

35. The compound of claim 34 wherein in R_n, n is 1 and R is methyl or halo.

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

37. The compound of claim 1 wherein W is --C(R₃)_p H.sub.(2-p) -- and p is 2.

38. The compound of claim 1 wherein in R_n, n is 1 and R is on the carbon atom adjacent to Z₁ on the furan ring.

39. The compound of claim 1 wherein the first amine substituent is a 5-membered heteroaryl chosen from the group consisting of furan and thiophene.

40. 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 ##STR4## 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 0-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 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) 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 cycle group with Q which is 1-methylcyclopropyl, 1-methylcyclobutyl, 1-methylcyclopentyl, or 1-methylcyclohexyl;

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.

41. The method of claim 40 wherein A is --C(O)-amine wherein the first amine substituent is a C₂ -C₆ straight or branched alkyl or alkenyl group optionally substituted with one or more halogen and the second amine substituent is hydrogen.

42. The method of claim 41 wherein in --W_m --, m is 0.

43. The method of claim 42 wherein Q is Si.

44. The method of claim 43 wherein each R₂ is independently selected from alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, and phenyl.

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

46. The method of claim 45 wherein each R₂ is methyl.

47. The method of claim 46 wherein A is alkylaminocarbonyl or dialkylaminocarbonyl.

48. The method of claim 47 wherein A is ethylaminocarbonyl.

49. The method of claim 48 wherein in R_n, n is 1 and R is methyl or halo.

50. The method of claim 41 wherein W_m is --O-- and Q is C.

51. The method of claim 50 wherein R₂ is C1-C4 alkyl or haloalkyl.

52. The method of claim 51 wherein A is alkylaminocarbonyl or dialkylaminocarbonyl.

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

54. The method of claim 53 wherein in R_n, n is 1 and R is methyl or halo.

55. The method of claim 41 wherein W_m is --NH-- or --N(CH₃)-- and Q is C.

56. The method of claim 55 wherein R₂ is C1-C4 alkyl or haloalkyl.

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

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

59. The method of claim 58 wherein in R_n, n is 1 and R is methyl or halo.

60. The method of claim 40 wherein the first amine substituent is a 5-membered heteroaryl chosen from the group consisting of furan and thiophene.

61. The method of claim 40 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.