Aromatic amides, their preparation process and their use as pesticides

• US 20030225302A1
• Filed: 05/02/2003
• Published: 12/04/2003
• Est. Priority Date: 07/02/1997
• Status: Abandoned Application

• Current Assignee: Hoechst Schering Agrevo SA (Bayer AG)
• Original Assignee: Hoechst Schering Agrevo SA (Bayer AG)
• Inventors: Peek, Robert, Weston, John, Ugolini, Antonio, Demassey, Jacques
• Application Number:
  US10/429,112
• Publication Number:
  US 20030225302A1
• Time in Patent Office: Days
• US Class Current: 564/171
• CPC Class Codes: A01N 37/22 the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
• 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 235/84 with the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
• CPC Class Codes: C07C 251/40 to carbon atoms of an unsaturated carbon skeleton
• CPC Class Codes: C07D 295/32 acylated with carboxylic or carbonic acids, or their nitrogen or sulfur analogues

Abstract

Aromatic amides, their preparation process and their use as pesticides

Compounds of formula (I):

in which

a, b, c, d and e identical to or different from one another, represent a hydrogen atom, a halogen atom, an alkyl, alkenyl or alkynyl, O-alkyl, O-alkenyl or O-alkynyl, S-alkyl, S-alkenyl or S-alkynyl, each radical containing up to 8 carbon atoms, optionally substituted by one or more halogen atoms, a SF₅, C N, NO₂ or NH₂ radical, the substituents a, b, c and d being able to form between themselves rings which either carry or do not carry one or more heteroatoms and being able to be substituted;

X and Y or Y and Z identical or different, represent a radical: —HC═CH—, —(CH₃)C═CH—, -(Hal)C═C—, ═C(f)(g), or ═C═Cx¹x²,

Hal represents a halogen atom:

X¹ represents a hydrogen atom or a halogen atom, in which f and g, identical to or different from each other, represent a hydrogen atom, a halogen atom, a free, etherified or esterified hydroxyl radical, an alkyl radical, containing up to 8 carbon atoms, optionally substituted by one or more halogen atoms, or represent a C═O radical, an oxygen atom;

X′ represents an oxygen or sulphur atom,

R¹ and R² identical to or different from each other, represent a hydrogen atom, a linear, branched or cyclic, saturated or unsaturated alkyl, CO-alkyl or CO₂-alkyl radical, containing up to 8 carbon atoms, optionally interrupted by one or more heteroatoms, optionally substituted, or an optionally substituted aryl or heteroaryl radical, the —C(X′)—NR¹R² chain being in meta or para position, and

dotted lines representing one or more optional double bonds,

in all their possible isomeric forms as well as their mixture.

The compounds of formula (I) have pesticidal properties.

Claims

1. Compounds of formula (1):

2. The compounds of formula (I) defined in claim 1, in the —

C(X′

)—

NR¹R².

3. The compounds of formula (I) defined in claim 1 or 2, in which X′

represents an oxygen atom.

4. The compounds of formula (I) defined in claim 1, 2 or 3, in which R¹ represents a hydrogen atom.

5. The compounds of formula (I) defined in any one of claims 1 to 4, in which R₂ represents an aryl radical, optionally substituted.

6. The compounds of formula (I) defined in any one of claims 1 to 4, in which R₂ represents an alkyl radical containing up to 8 carbon atoms, linear or branched.

7. The compounds of formula (I) defined in any one of claims 1 to 6, in which at least one of the substituents a, b, c, d and e represent a halogen atom.

8. The compounds of formula (I) defined in claim 7, in which the halogen is chlorine or bromine.

9. The compounds of formula (I) defined in claim 7 or 8, in which b, c and d each represent a chlorine or hydrogen atom.

10. The compounds of formula (I) defined in any one of claims 1 to 9, in which a and e each represent a hydrogen atom.

11. The compounds of formula (I) defined in any one of claims 1 to 10, in which Z represents a —

CH₂—

radical.

12. The compounds of formula (I) defined in any one of claims 1 to 11, in which X represents a —

CH₂—

radical.

13. The compounds of formula (I) defined in any one of claims 1 to 11, in which X and Y together represent a —

HC═

CH—

radical.

14. The compounds of formula (I) defined in any one of claims 1 to 10 in which Y and Z together represent a —

HC═

CH—

radical.

15. The compounds of formula (I) defined in any one of claims 1 to 11, in which X and Y represent a radical —

FC═

CH—

, —

(CH₃C═

CH—

or —

CH═

CF—

.

17. A process for preparing compounds of formula (I) defined in any one of claims 1 to 16, wherein a compound of formula (II):

18. As chemical products, the compounds of formula (II) defined in claim 17.

19. A process for combating arthropodos and/or helminths and/or molluscs, which comprises the administration to the arthropods and/or helminths and/or molluscs, or to their environment, of a quantity of a compound of formula (I), as defined in any of claims 1 to 16, which is sufficient to destroy the harmful organism.

20. A process for combating and/or eradicating infestations by arthropods and/or helminths and/or molluscs in animals (including humans) and/or plants (including trees) and/or stored products, which comprises the administration to the animal or to the locality of an effective quantity of a compound of formula (I), as defined in any of claims 1 to 16.

22. A composition comprising:

a) a compound of formula (I), as defined in any of claims 1 to 16,

b) inert excipients suitable for use as pesticides of the said product of formula (I).

23. A composition comprising:

a) a compound of formula (I), as defined in any of claims 1 to 16,

b) inert excipients suitable for use in the veterinary field of the said product of formula (I).

16. The compounds of formula (I) the names of which follow:

4-[3-(3,4-dichlorophenyl)-2-fluoropropyl]-N-(2-methyl-phenyl)-benzamide

4-[3-(3,4-dichlorophenyl)-2-fluoropropyl]-N-(1,2-dimethyl-propyl)-benzamide

4-[3 (3,4-dichlorophenyl)-2-fluoropropyl]-N-(4-fluoro-2-methylphenyl)-benzamide

4-[3-(3,4-dichlorophenyl)-3-fluoropropyl]-N-(2-methyl-phenyl)-benzamide

4-[3-(3,4-dichlorophenyl)-2-propenyl]-N-(2-methylphenyl)-benzamide

4-[3-(4-bromo-2-methylphenyl)-2-propenyl]-N-(2-methyl-phenyl)-benzamide

4-[3-(3,4-dichlorophenyl)-2-fluorobutyl]-N-(2-methyl-phenyl)-benzamide

4-[3-(3,4-dichlorophenyl)-2-butenyl]-N-(2-methylphenyl)-benzamide

4-[3-chloro-3-(3,4-dichlorophenyl]-2-propenyl]-N-(2-methylphenyl)-benzamide

4-[3-chloro-3-(3,4-dichlorophenyl]-2-propenyl]-N-(2-methylphenyl)-benzamide

4-[3-(3,4-dichlorophenyl)-2-butenyl]-N-(1,2-dimethyl-propyl]-benzamide

4-[3-(3,4-dichlorophenyl)-2-fluoro-2-propenyl]-N-(2-methylphenyl)-benzamide

4-[3-(3,4-dichlorophenyl)-2-fluoro-2-propenyl]-N-ethyl-N-(2-methylphenyl)-benzamide

4-[3-(3,4-dichlorophenyl)-2-pentenyl]-N-2-methylphenyl)-benzamide.

21. Compounds of formula (I) to be used in human and veterinary medicine, in public health and/or in agriculture for combating harmful arthropods and/or helminths.