Nematicidal n-(2-substituted 2-phenylethyl)carboxamides and n-(2-substituted 2-phenylethyl)-thiocarboxamides

Patent metadata

Field	Value
Publication number	US-2016100579-A1
Application number	US-201414787533-A
Country	US
Kind code	A1
Filing date	Apr 25, 2014
Priority date	Apr 30, 2013
Publication date	Apr 14, 2016
Grant date	—

Abstract

The present invention relates to the use of known and novel N-(2-substituted 2-phenylethyl)carboxamides and N-(2-substituted 2-phenylethyl)thiocarboxamides, for the control of plant damaging nematodes in agriculture and further relates to novel N-(2-substituted 2-phenylethyl)carboxamides and N-(2-substituted 2-phenylethyl)thiocarboxamides, processes and intermediate compounds for their preparation, their use as nematicides and their use as anthelmintics against endoparasites in animals and humans, compositions containing such compounds and methods for the control of nematodes and helminths.

First claim

1 . A compound of formula (I)

wherein
A represents phenyl of formula A a

wherein
* indicates the bond which connects A a to the C=T moiety of the compound of formula (I),
Y 1 represents halogen, nitro, SH, SF 5 , CHO, OCHO, NHCHO, cyano, C 1 -C 8 -alkyl, C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halogenocycloalkyl having 1 to 9 halogen atoms, C 1 -C 8 -alkylsulfanyl, —C 1 -C 8 -halogenoalkylsulfanyl having 1 to 5 halogen atoms, C 1 -C 8 -alkoxy, C 1 -C 8 -halogenoalkoxy having 1 to 5 halogen atoms, C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl, C 2 -C 8 -alkenyloxy-C 1 -C 8 -alkyl, C 3 -C 8 -alkynyloxy-C 1 -C 8 -alkyl, C 2 -C 8 -alkenyloxy, C 3 -C 8 -alkynyloxy, C 1 -C 8 -alkoxycarbonyl, C 1 -C 8 -halogenoalkoxycarbonyl having 1 to 5 halogen atoms, C 1 -C 8 -alkylcarbonyloxy, C 1 -C 8 -halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, C 1 -C 8 -alkylsulfinyl, C 1 -C 8 -halogenoalkylsulfinyl having 1 to 5 halogen atoms, C 1 -C 8 -alkylsulfonyl, C 1 -C 8 -halogenoalkylsulfonyl having 1 to 5 halogen atoms, C 1 -C 8 -alkylsulfonamide, substituted or unsubstituted tri-(C 1 -C 8 )-alkylsilyl, substituted or unsubstituted aryl and substituted or unsubstituted aryloxy;
Y 2 , Y 3 , Y 4 and Y 5 independently from each other represent hydrogen or Y 1 ; or
A represents a carbo-linked heterocyclyl group selected from the group consisting of A 1 to A 33 wherein
A 1 is a heterocycle of formula (A 1 )

wherein
R 1 to R 3 independently from each other represent hydrogen, halogen, substituted or unsubstituted C 1 -C 5 -alkyl, C 1 -C 5 -halogenoalkyl comprising 1 to 9 halogen atoms, substituted or unsubstituted C 1 -C 5 -alkoxy or C 1 -C 5 -halogenoalkoxy comprising 1 to 9 halogen atoms,
A 2 is a heterocycle of formula (A 2 )

wherein
R 4 to R 6 independently from each other represent hydrogen, halogen, substituted or unsubstituted C 1 -C 5 -alkyl, C 1 -C 5 -halogenoalkyl comprising 1 to 9 halogen atoms, substituted or unsubstituted C 1 -C 5 -alkoxy or C 1 -C 5 -halogenoalkoxy comprising 1 to 9 halogen atoms,
A 3 is a heterocycle of formula (A 3 )

wherein
R 7 represents hydrogen, halogen, substituted or unsubstituted C 1 -C 5 -alkyl, C 1 -C 5 -halogenoalkyl comprising 1 to 9 halogen atoms, substituted or unsubstituted C 1 -C 5 -alkoxy or C 1 -C 5 -halogenoalkoxy comprising 1 to 9 halogen atoms, and
R 8 represents hydrogen or substituted or unsubstituted C 1 -C 5 -alkyl,
A 4 is a heterocycle of formula (A 4 )

wherein
R 9 to R 11 independently from each other represent hydrogen, halogen, substituted or unsubstituted C 1 -C 5 -alkyl, amino, substituted or unsubstituted C 1 -C 5 -alkoxy, substituted or unsubstituted C 1 -C 5 -alkylsulphanyl, C 1 -C 5 -halogenoalkyl comprising 1 to 9 halogen atoms or C 1 -C 5 -halogenoalkoxy comprising 1 to 9 halogen atoms,
A 5 is a heterocycle of formula (A 5 )

wherein
R 12 and R 13 independently from each other represent hydrogen, halogen, substituted or unsubstituted C 1 -C 5 -alkyl, substituted or unsubstituted C 1 -C 5 -alkoxy, amino, C 1 -C 5 -halogenoalkyl comprising 1 to 9 halogen atoms or C 1 -C 5 -halogenoalkoxy comprising 1 to 9 halogen atoms, and
R 14 represents hydrogen, halogen, substituted or unsubstituted C 1 -C 5 -alkyl, substituted or unsubstituted C 1 -C 5 -alkoxy, amino, C 1 -C 5 -halogenoalkyl comprising 1 to 9 halogen atoms or C 1 -C 5 -halogenoalkoxy comprising 1 to 9 halogen atoms,
A 6 is a heterocycle of formula (A 6 )

wherein
R 15 represents hydrogen, halogen, cyano, substituted or unsubstituted C 1 -C 5 -alkyl, substituted or unsubstituted C 1 -C 5 -alkoxy, C 1 -C 5 -halogenoalkoxy comprising 1 to 9 halogen atoms or C 1 -C 5 -halogenoalkyl comprising 1 to 9 halogen atoms, and
R 16 and R 18 independently from each other represent hydrogen, halogen, substituted or unsubstituted C 1 -C 5 -alkoxycarbonyl, substituted or unsubstituted C 1 -C 5 -alkyl, C 1 -C 5 -halogenoalkoxy comprising 1 to 9 halogen atoms or C 1 -C 5 -halogenoalkyl comprising 1 to 9 halogen atoms, and
R 17 represents hydrogen or substituted or unsubstituted C 1 -C 5 -alkyl,
A 7 is a heterocycle of formula (A 7 )

wherein
R 19 represents hydrogen or substituted or unsubstituted C 1 -C 5 -alkyl, and
R 20 to R 22 independently from each other represent hydrogen, halogen, substituted or unsubstituted C 1 -C 5 -alkyl or C 1 -C 5 -halogenoalkyl comprising 1 to 9 halogen atoms,
A 8 is a heterocycle of formula (A 8 )

wherein
R 23 represents hydrogen, halogen, substituted or unsubstituted C 1 -C 5 -alkyl or C 1 -C 5 -halogenoalkyl comprising 1 to 9 halogen atoms, and
R 24 represents hydrogen or substituted or unsubstituted C 1 -C 5 -alkyl or C 1 -C 5 -halogenoalkyl comprising 1 to 9 halogen atoms,
A 9 is a heterocycle of formula (A 9 )

wherein
R 25 represents hydrogen, halogen, substituted or unsubstituted C 1 -C 5 -alkyl or C 1 -C 5 -halogenoalkyl comprising 1 to 9 halogen atoms, and
R 26 represents hydrogen, substituted or unsubstituted C 1 -C 5 -alkyl or C 1 -C 5 -halogenoalkyl comprising 1 to 9 halogen atoms,
A 10 is a heterocycle of formula (A 10 )

wherein
R 27 represents hydrogen, halogen, substituted or unsubstituted C 1 -C 5 -alkyl or C 1 -C 5 -halogenoalkyl comprising 1 to 9 halogen atoms, and
R 28 represents hydrogen, halogen, substituted or unsubstituted C 1 -C 5 -alkyl, C 1 -C 5 -halogenoalkyl comprising 1 to 9 halogen atoms, C 1 -C 5 -halogenoalkoxy comprising 1 to 9 halogen atoms, amino, substituted or unsubstituted C 1 -C 5 -alkylamino or substituted or unsubstituted di-(C 1 -C 5 -alkyl)-amino,
A 11 is a heterocycle of formula (A 11 )

wherein
R 29 represents hydrogen, halogen, substituted or unsubstituted C 1 -C 5 -alkyl, substituted or unsubstituted C 1 -C 5 -alkoxy, C 1 -C 5 -halogenoalkoxy comprising 1 to 9 halogen atoms or C 1 -C 5 -halogenoalkyl comprising 1 to 9 halogen atoms, and
R 30 represents hydrogen, halogen, substituted or unsubstituted C 1 -C 5 -alkyl, C 1 -C 5 -halogenoalkyl comprising 1 to 9 halogen atoms, C 1 -C 5 -halogenoalkoxy comprising 1 to 9 halogen atoms, amino, substituted or unsubstituted C 1 -C 5 -alkylami

Assignees

• Bayer Cropscience Ag

Inventors

• Decor Anne
• Greul Joerg Nico
• Schwarz Hans-Georg
• Hoffmann Sebastian
• Willms Lothar
• Sudau Alexander
• Fuesslein Martin
• Loesel Peter
• Luemmen Peter
• Goergens Ulrich
• Portz Daniela
• Ilg Kerstin
• Malsam Olga
• Heilmann Eike Kevin
• Coqueron Pierre-Yves
• Sasaki Norio
• Desbordes Philippe
• Tsuchiya Tomoki

Classifications

• A61P33/00

  Antiparasitic agents · CPC title

• A01N43/60 Primary

  1,4-Diazines; Hydrogenated 1,4-diazines · CPC title

• C07D307/68

  Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen · CPC title

• C07C233/73

  of a carbon skeleton containing six-membered aromatic rings · CPC title

• C07D333/38

  Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals · CPC title