Fungicidal compositions based on pyridylmethylbenzamide derivatives and at least one complex III inhibiting compound

• US 20040106578A1
• Filed: 09/08/2003
• Published: 06/03/2004
• Est. Priority Date: 03/08/2001
• Status: Abandoned Application

• Current Assignee: Bayer Cropscience SA (Bayer AG)
• Original Assignee: Bayer Cropscience SA (Bayer AG)
• Inventors: Latorse, Marie-Pascale, Mercer, Richard, Holah, David Stanley, Dancer, Jane Elisabeth
• Application Number:
  US10/471,124
• Publication Number:
  US 20040106578A1
• Time in Patent Office: Days
• US Class Current: 514/63
• CPC Class Codes: A01N 2300/00 Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
• CPC Class Codes: A01N 37/50 the nitrogen atom being doubly bound to the carbon skeleton
• CPC Class Codes: A01N 43/24 with two or more hetero atoms
• CPC Class Codes: A01N 43/40 six-membered rings
• CPC Class Codes: A01N 43/50 1,3-Diazoles; Hydrogenated 1,3-diazoles
• CPC Class Codes: A01N 43/54 1,3-Diazines; Hydrogenated 1,3-diazines
• CPC Class Codes: A01N 43/76 1,3-Oxazoles; Hydrogenated 1,3-oxazoles
• CPC Class Codes: A01N 47/24 containing the groups , or; Thio analogues thereof
• CPC Class Codes: A01N 61/00 Biocides, pest repellants or attractants, or plant growth regulators containing substances of unknown or undetermined composition, e.g. substances characterised only by the mode of action

Abstract

1) Fungicidal compositions comprising: a) at least one pyridylmethylbenzamide derivative of Formula (1), in which the various radicals are as defined in the description; and b) at least one compound (11) capable of inhibiting the transport of electrons of the respiratory chain of mitochondrial ubiquinol:ferricytochrome-c oxidoreductase or complex III in phytopathogenic fungal organisms. 2) Process for curatively or preventively controlling the phytopathogenic fungi of crops, characterized in that an effective and nonphytotoxic quantity of one of these fungicidal compositions is applied to the aerial parts of plants.

Claims

1. A fungicidal composition comprising:

a) at least one compound (I) which is a pyridylmethylbenzamide derivative of formula (I);

 

in which;

R¹ is chosen from a hydrogen atom, an unsubstituted or substituted alkyl radical and an unsubstituted or substituted acyl or alkoxycarbonyl radical;

R² is chosen from a hydrogen atom and an unsubstituted or substituted alkyl radical;

R³ and R⁴, which are identical or different, are independently chosen from a halogen atom, the hydroxyl radical, the cyano radical, the nitro radical, the —

SF₅ radical, the trialkylsilyl radical, an unsubstituted or substituted amino radical, an acyl radical, an alkoxycarbonyl radical and a group E, OE or SE, in which E is chosen from an alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl and heterocyclyl radical, each of which is unsubstituted or substituted;

c represents 0, 1, 2, 3, 4 or 5;

q represents 0, 1, 2, 3 or 4;

 

or an agriculturally acceptable acid addition salt thereof; and

b) at least one compound (II) capable of inhibiting the transport of electrons of the respiratory chain of mitochondrial ubiquinol;

ferricytochrome-c oxidoreductase (complex III) in phytopathogenic fungal organisms; and

an agriculturally acceptable carrier and/or surfactant.

2. A fungicidal composition according to claim 1, characterized in that compound (I) possesses at least one of the following characteristics, taken in isolation or in combination:

R¹ and R² which are identical or different, are independently chosen from a hydrogen atom and an unsubstituted or substituted alkyl radical;

R³ and R⁴, which are identical or different, are independently chosen from a halogen atom, the hydroxyl radical, the nitro radical, an unsubstituted or substituted amino radical, an acyl radical, and a group E, OE or SE, in which E is chosen from an alkyl, cycloalkyl, phenyl and heterocyclyl radical, each of which is unsubstituted or substituted;

c represents 0, 1, 2 or 3;

q represents 0, 1, 2 or 3.

3. A fungicidal composition according to claim 1, characterized in that compound (I) possesses at least one of the following characteristics, taken in isolation or in combination:

R¹ and R², which are identical or different, are independently chosen from a hydrogen atom and a methyl or ethyl radical;

R³ and R⁴, which are identical or different, are independently chosen from a halogen atom, the nitro radical, an optionally substituted amino radical and an alkyl, cycloalkyl, phenyl or heterocyclyl radical, each of which is unsubstituted or substituted;

c represents 1 or 2;

q represents 1 or 2.

4. A fungicidal composition according to claim 1, characterized in that compound (I) possesses at least one of the following characteristics:

R¹ and R² each represent a hydrogen atom;

R³ and R⁴, which are identical or different, are independently chosen from a halogen atom, the nitro radical, an alkyl radical and the trifluoromethyl radical;

c and q represent, independently of each other, 2.

5. A fungicidal composition according to claim 1, characterized in that the compound of formula (I) is chosen from:

2,6-dichloro-N-{[3-chloro-5-(trifluoromethyl)-2-pyridinyl]methyl}benzamide;

N-{[3-chloro-5-(trifluoromethyl)-2-pyridinyl]methyl}-2-fluoro-6-nitrobenzamide; and

N-{[3-chloro-5-(trifluoromethyl)-2-pyridinyl]methyl}-2-methyl-6-nitrobenzamide,

and their agriculturally acceptable acid addition salts.

6. A fungicidal composition according to any one of the preceding claims, characterized in that compound (II) is chosen from the compounds (IIa) capable of inhibiting the reduction of a ubiquinone, at a domain of complex III called Q_in or Q_i.

7. A fungicidal composition according to any one of claims 1 to 5, characterized in that compound (II) is chosen from the compounds (IIb) capable of inhibiting the reduction of ubiquinol, at a domain of complex III called Q_out or Q_o.

8. A fungicidal composition according to claim 6, characterized in that compounds (IIa) are chosen from cyazofamid and antimycin.

9. A fungicidal composition according to claim 7 characterized in that compounds (IIb) are chosen from azoxystrobin, dicostrobin, kresomim-methyl, metominostrobin, pyraclostrobin, pycoxystrobin, trifloxystrobin, fenamidone and famoxadone.

10. A fungicidal composition according to any one of the preceding claims, characterized in that compound (I) is chosen from 2,6-dichloro-N-{[3-chloro-5-(trifluoromethyl)-2-pyridinyl]methyl}benzamide;

N-{[3-chloro-5-(trifluoromethyl)-2-pyridinyl]methyl}-2-fluoro-6-nitrobenzamide and N-{[3-chloro-5-(trifluoromethyl)-2-pyridinyl]methyl}-2-methyl-6-nitrobenzamide and compound (II) is chosen from cyazofamid, antimycin, azoxystrobin, dicostrobin, kresomim-methyl, metominostrobin, pyraclostrobin, pycoxystrobin, trifloxystrobin, fenamidone and famoxadone.

11. A fungicidal composition according to any one of the preceding claims, characterized in that compound (I) is 2,6-dichloro-N-{[3-chloro-5-(trifluoromethyl)-2-pyridinyl]methyl}benzamide and compound (II) is fenamidone.

12. A fungicidal composition according to any one of the preceding claims, characterised in that the ratio by weight of the compound (I)/compound (II) is from 1/10 to 10/1.

13. A fungicidal composition according to claim 12, characterized in that the ratio is from 1/5 to 5/1.

14. Fungicidal compositions according to claim 13, characterized in that the ratio is from 1/5 to 2/1.

15. A fungicidal composition according to any one of the preceding claims, which comprises from 0.5 to 99% by weight of the combination of compound (I) and compound (II).

16. Method for controlling phytopathogenic fungi of a crop at a locus which comprises applying thereto a compound (I) and compound (II) as defined in claim 1.

17. Method according to claim 16 for controlling, curatively or preventively, phytopathogenic fungi of a crop, characterized in that an effective (agronomically effective) and nonphytotoxic quantity of a fungicidal composition according to any one of claims 1 to 15 is applied to the soil where plants grow or are capable of growing, to the leaves and/or the fruit of plants or to the seeds of plants.

18. Method according to claim 16, characterized in that the fungicidal composition is applied by spraying a liquid on the aerial parts of a crop to be treated.

19. Method according to claim 17 or 18, characterized in that the quantity of fungicidal composition corresponds to a dose of compound (I) and of compound (II) from about 0.1 g/ha to about 200 g/ha.

20. Method according to claim 17, 18 or 19, characterized in that the crop treated is grapevine.

21. Method according to the preceding claim, characterized in that the phytopathogenic fungus treated is vine downy mildew.

22. Product comprising a compound (I) and a compound (II) as defined in claim 1 as a combined preparation for simultaneous, separate or sequential use in controlling phytopathogenic fungi of a crop.