Fungicides for the control of take-all disease of plants

• US 6,252,078 B1
• Filed: 09/28/1998
• Issued: 06/26/2001
• 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): Lambkin, Deborah C.
• Application Number:
  US09/162,032
• Time in Patent Office: 1,002 Days
• Field of Search: 546/169, 546/14, 514/354
• US Class Current: 546/14
• 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 a plant caused by Gaeumannomyces sp. comprising applying to the plant locus a fungicidally effective amount of a fingicide of the formula:

wherein A is selected from the group consisting of —

C(X)-amine, wherein the amine is substituted with a first and a second amine substituent respectively, —

C(O)—

SR₃, —

NH—

C(X)R₄ and —

C(═

NR₃)—

XR₇ or an alkylaminocarbonyl and a hydrogen;

wherein X is O or S;

wherein 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;

wherein B is —

W_m—

Q(R₂)₃;

Q is C or Si;

W is —

C(R₃)_pH<sub>(2−

p)</sub>—

, —

N(R₃)_mH<sub>(1−

m</sub>)—

, —

S(O)_p—

, or —

O—

;

m is 0 or 1;

p is 0, 1, or 2;

each R₂ is independently selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl and phenyl, each optionally substituted with R₄ or halogen;

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;

wherein R is 0, 1, 2, 3 or 4 and 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, alkylsufinyl, 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.

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 alkynyl group optionally substituted with one or more halogen and the second amine substituent is hydrogen.

3. The method of claim 2 wherein W_m is —

O— and

Q is C.

4. The method of claim 3 wherein R₂ is C₁-C₄ alkyl or haloalkyl.

5. The method of claim 2 wherein A is ethylaminocarbonyl.

6. The method of claim 5 wherein there is only one R group, which is methyl or halo.

7. 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.

8. The method of claim 5 wherein R is adjacent to A.

9. The method of claim 2 wherein m is 0 and Q is Si.

10. The method of claim 3 wherein R is 0.