Aromatic amides, method for preparing and compositions containing same, and use thereof as pesticides

• US 6,013,837 A
• Filed: 07/30/1997
• Issued: 01/11/2000
• Est. Priority Date: 01/26/1995
• Status: Expired due to Fees

• Current Assignee: Hoechst Schering Agrevo SA (Bayer AG)
• Original Assignee: Hoechst Marion Roussel (Sanofi )
• Inventors: Gohar, Michel, Wehrey, Christian, Demassey, Jacques
• Primary Examiner(s): Dees, Jose' G.
• Assistant Examiner(s): QAZI, SABIHA NAIM
• Application Number:
  US08/894,068
• Time in Patent Office: 895 Days
• Field of Search: 564/123, 564/155, 564/160
• US Class Current: 564/155
• CPC Class Codes: A01N 37/10 Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
• 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 37/22 the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
• CPC Class Codes: A01N 37/36 containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
• CPC Class Codes: A01N 37/38 having at least one oxygen or sulfur atom attached to an 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 37/46 N-acyl derivatives
• CPC Class Codes: A01N 37/48 Nitro-carboxylic acids; Derivatives thereof
• CPC Class Codes: A01N 41/10 Sulfones; Sulfoxides
• CPC Class Codes: A01N 43/10 with sulfur as the ring hetero atom
• CPC Class Codes: A01N 43/36 five-membered rings
• CPC Class Codes: A01N 43/40 six-membered rings
• CPC Class Codes: A01N 43/44 three- or four-membered rings
• CPC Class Codes: A01N 43/713 having rings with four or more nitrogen atoms as the only ring hetero atoms
• CPC Class Codes: A01N 43/78 1,3-Thiazoles; Hydrogenated 1,3-thiazoles
• CPC Class Codes: A01N 43/80 five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
• CPC Class Codes: A01N 43/84 six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
• CPC Class Codes: A61P 31/00 Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
• CPC Class Codes: A61P 33/00 Antiparasitic agents
• 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 233/75 : with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
• CPC Class Codes: C07C 235/42 : having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
• CPC Class Codes: C07D 203/12 : Radicals substituted by nitrogen atoms not forming part of a nitro radical
• CPC Class Codes: C07D 205/12 : condensed with carbocyclic rings or ring systems
• CPC Class Codes: C07D 207/09 : Radicals substituted by nitrogen atoms, not forming part of a nitro radical
• CPC Class Codes: C07D 207/267 : with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atom
• CPC Class Codes: C07D 213/40 : Acylated substituent nitrogen atom
• CPC Class Codes: C07D 213/61 : Halogen atoms or nitro radicals
• CPC Class Codes: C07D 257/06 : with nitrogen atoms directly attached to the ring carbon atom
• CPC Class Codes: C07D 261/08 : with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 277/28 : Radicals substituted by nitrogen atoms
• CPC Class Codes: C07D 307/14 : Radicals substituted by nitrogen atoms not forming part of a nitro radical
• CPC Class Codes: C07D 333/20 : by nitrogen atoms nitro, nitroso radicals C07D333/12

Abstract

The subject of the invention is the compounds of formula (I):

Q(CH.sub.2)a-(X.sub.1).sub.b -Q.sub.1 -Q.sub.2

-C(X₂)--N(R₁)(R₂) (I)

in which:

Q represents an aryl radical,

X₁ represents oxy, thio, sulphinyl or sulphonyl,

X₂ represents oxygen or sulphur,

Q₁ represents a cyclopropanediyl radical,

Q₂ represents an arylene radical,

R₁ and R₂ represent:

either a hydrogen atom or a hydrocarbon radical or one of the groups

R.sub.3 --C═X.sub.3, (R.sub.3).sub.2 --P═X.sub.3, T.sub.2 -R.sub.5

or S(O)_j --N(R₆)(R₇)

in which X₃ represents an oxygen atom or a sulphur atom, T₂ represents a bivalent oxy, carbonyl or oxycarbonyl group and j is equal to 0, 1 or 2, their preparation process and their use as pesticides.

Claims

1. A compound selected from the group consisting of all stereoisomeric forms and mixtures thereof of a compound of the formula ##STR12## wherein Q and Q₂ are individually selected from the group consisting of aryl and naphthyl unsubstituted or substituted by at least one member of the group consisting of halogen, methylenedioxy, difluoromethylenedioxy, tetrafluoroethylenedioxy, --CN, --NO₂, cyanato, thiocyanato, pentafluorothio and fluorosulfonyl, a and b are individually 0 or 1, X₁ and X₂ are --O-- or --S--, Q₁ is cyclopropanediyl unsubstituted or substituted with 1 to 2 halogens and R₁ and R₂ are individually selected from the group consisting of hydrogen, saturated or unsaturated hydrocarbon of up to 12 carbon atoms and aryl of up to 12 carbon atoms.

2. A compound of claim 1 wherein Q is phenyl or naphthyl unsubstituted or substituted with 1 to 3 substituents of claim 1.

3. A compound of claim 1 wherein Q-(CH₂)_a -(X₁)_b is in trans position to ##STR13##

4. a compound of claim 1 wherein Q₁ is unsubstituted or substituted with 1 to 2 methyl(s) or 1 to 2 halogens.

5. A compound of claim 1 wherein Q is selected from the group consisting of phenyl, 2-chloro phenyl, 3-chloro phenyl, 3-bromophenyl, 3-(trifluoromethyl) phenyl, 4-chloro phenyl, 4-bromo phenyl, 4-iodo phenyl, 4-(trifluoromethyl) phenyl, 4-nitrophenyl, 4-methoxy phenyl, 4-(difluoromethoxy) phenyl, 4-(trifluoro-methoxy) phenyl, 3-bromo 4-(difluoromethoxy) phenyl, 4-(2,2-dibromo ethenyl) phenyl, 4-ethynyl phenyl, 4-benzyl phenyl, 3,4-dibromo phenyl, 2,4-dichlorophenyl, 3,4-dichloro phenyl, 3,4-difluorophenyl, 3-chloro 4-iodo phenyl, 4-bromo 3-chloro phenyl, 4-bromo 2-fluoro phenyl, 4-bromo 3-fluoro phenyl, 4-bromo 3-(trifluoromethyl) phenyl, 4-chloro 3-(trifluoro-methyl) phenyl, 3,5-bis(trifluoromethyl) phenyl, 3,4,5-trichloro phenyl, 4-bromo 3,5-dichloro phenyl, 3-phenoxyphenyl, 4-(fluoro 3-phenoxy) phenyl, 3-bromo 4-(trifluoromethylsulphonyloxy) phenyl, 3,4-bis(trifluoro-methylsulphonyloxy) phenyl, 2-naphthyl, 5-bromo 2-naphthyl and 6-bromo 1-napthyl.

6. A compound of claim 1 wherein Q₁ is selected from the group consisting of 1,2-cyclopropanediyl, 1-fluoro 1,2-cyclopropanediyl, 1-chloro 1,2 -cyclopropanediyl, 1-bromo 1,2-cyclopropanediyl, 1-methyl 1,2-cyclopropanediyl, 3,3-dibromo 1,2-cyclopropanediyl and 1,2-difluoro 1,2-cyclopropanediyl.

7. A compound of claim 1 wherein Q₂ is selected from the group consisting of ortho-phenylene, meta-phenylene, paraphenylene, 1,2-naphthylene, 1,3-naphthylene, 1,4-naphthylene, 1,5- naphthylene, 2,5-naphthylene, 4,5-indenylene, 4,6-indenylene, 4,7-indenylene, 4,5-indanylene, 4,6-indanylene, 4,7-indanylene, 1,2,3,4-tetrahydro 5,6-naphthylene, 1,2,3,4-tetrahydro 5,7-naphthylene, 1,2,3,4-tetrahydro 5,8-naphthylene, non substituted or substituted by 1 to 4 substituants.

8. A compound of claim 1 wherein Q₂ is selected from the group consisting of 2-methyl-1,4-phenylene, 2,3,5,6-tetrafluoro 1,4-phenylene, 3-methyl 1,4-phenylene, 2-chloro 1,4-phenylene, 2-acetylamino 5-chloro 1,4-phenylene, 2-amino 5-chloro 1,4-phenylene, 2-dimethyl-amino 5-chloro 1,4-phenylene.

9. A compound of claim 1 wherein R₂ is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms, benzyl, an ethoxymethyl, a propoxymethyl.

10. A compound of claim 1 wherein selected from the group consisting of ka and b are 0. -4-(1-fluoro 2-phenyl cyclopropyl) N-isobutyl benzenamide (cis+trans isomers, cis/trans=3/2)

4-(1-fluoro 2-phenyl cyclopropyl) N-(2-methyl phenyl) -benzenamide (cis+trans isomers, cis/trans=3/1)

4-[2-(4-chloro phenyl) cyclopropyl] N-isobutyl benzenamide (trans isomer)

4-[2-(4chloro phenyl) 1-fluoro cyclopropyl] N-ethyl N-(2-methyl phenyl) benzenamide (cis isomer)

4-[2-(3,4-dibromo phenyl) 1-fluoro cyclopropyl] -N-(2-methyl phenyl) benzenamide (cis isomer)

4-[2-(4chloro phenyl) 1-fluoro cyclopropyl] -N-isobutyl benzenamide (cis isomer)

4-[2-(4-chloro phenyl) 1-fluoro cyclopropyl] N-isobutyl benzenamide (cis isomer)

4-[2-(4-chloro phenyl) 1-fluoro cyclopropyl] -N-(2-methyl phenyl) benzenamide (cis isomer)

4-[2-(4-chloro phenyl) 1-fluoro cyclopropyl] N-isobutyl benzenamide (trans isomer)

4-[2-(4-chloro phenyl) 1-fluoro cyclopropyl] N-(2-methyl phenyl) benzenamide (trans isomer)

4-[2-(3,4-dichloro phenyl) 1-fluoro cyclopropyl] N-(2-methyl phenyl) benzenamide (cis isomer)

4-[2-dichloro phenyl) 1-fluoro cyclopropyl] N-ethyl N-(2-methyl phenyl) benzenamide (cis isomer)

4-[3,4,5-trichloro phenyl) 1-fluoro cyclopropyl] N-(2-methyl phenyl) benzenamide (cis isomer)

4-[2-(3,4-dibromo phenyl) 1-fluoro cyclopropyl] N-methyl N-(2-methyl phenyl) benzenamide (cis isomer)

4-[2-(4-trifluoromethoxy phenyl) 1-fluoro cyclopropyl] N-(2-methyl phenyl) benzenamide (cis isomer)

4-[2-(3,4-dibromo phenyl) 1-fluoro cyclopropyl] N-(2,6-dimethyl phenyl) benzenamide (cis isomer)

4-[2-(3,4-dibromo phenyl) 1-fluoro cyclopropyl] N-(2,4,6-trimethyl phenyl) benzenamide (cis isomer)

4-[2-(3,4-dichloro phenyl) 1-dluoro cyclopropyl] N-benzenamide (cis isomer)

4-[2-(3,4-dibromo phenyl) 1-fluoro cyclopropyl] N-(2-methyl phenyl) benzene thioamide (cis isomer)

4-[2-(3,4-dibromo phenyl) 1-fluoro cyclopropyl] N-ethyl N-(2-methyl phenyl) benzene thioamide (cis isomer)

4-[2-(3,4dibromo phenyl) 1-fluoro cyclopropyl] N-(1,4-oxazin-4-yl) benzenamide (cis isomer).

11. A compound of claim 1 wherein a and b are 0.