Carboxamide derivatives as pesticidal compounds

Patent metadata

Field	Value
Publication number	US-9776967-B2
Application number	US-201415022583-A
Country	US
Kind code	B2
Filing date	Oct 10, 2014
Priority date	Oct 14, 2013
Publication date	Oct 3, 2017
Grant date	Oct 3, 2017

Abstract

Disclosed are compounds of formula (I) which possess pesticidal, especially nematicidal properties wherein in the structural elements have the meaning as indicated in the description.

First claim

The invention claimed is:

1. A compound of formula (I)

or a salt, N-oxide, metal complex or metalloid complex thereof,
wherein
B 1 and B 2 are C—X or N, wherein at least one of B 1 or B 2 is N,
n is 0, 1, 2, 3 or 4, limited by the number of available positions in the ring to which a substituent X can be connected,
each X is independently selected from the group consisting of hydrogen, halogen, nitro, cyano, hydroxy, amino, —SH, —SF 5 , —CHO, —OCHO, —NHCHO, —COOH, —CONH 2 , —CONH(OH), —OCONH 2 , (hydroxyimino)-C 1 -C 6 -alkyl, 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 1 -C 8 -alkylamino, di-(C 1 -C 8 -alkyl)amino, C 1 -C 8 -alkoxy, C 1 -C 8 -halogenoalkoxy having 1 to 5 halogen atoms, C 2 -C 8 -alkenyloxy, C 2 -C 8 -halogenoalkenyloxy having 1 to 5 halogen atoms, C 3 -C 8 -alkynyloxy, C 3 -C 8 -halogenoalkynyloxy having 1 to 5 halogen atoms, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halogenocycloalkyl having 1 to 5 halogen atoms, C 1 -C 8 -alkylcarbonyl, C 1 -C 8 -halogenoalkylcarbonyl having 1 to 5 halogen atoms, —CONH(C 1 -C 8 -alkyl), —CON(C 1 -C 8 -alkyl) 2 , —CONH(OC 1 -C 8 -alkyl), —CON(C 1 -C 8 -alkyl)(C 1 -C 8 -alkyl), 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 -alkylcarbonylamino, C 1 -C 8 -halogenoalkylcarbonylamino having 1 to 5 halogen atoms, —OCONH(C 1 -C 8 -alkyl), —OCON(C 1 -C 8 -alkyl) 2 , —OCONH(OC 1 -C 8 -alkyl), —OCO(OC 1 -C 8 -alkyl), —S—C 1 -C 8 -alkyl, —S—C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 8 -alkyl, —S(O)—C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms, —S(O) 2 —C 1 -C 8 -alkyl, —S(O) 2 —C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms, (C 1 -C 6 -alkoxyimino)-C 1 -C 6 -alkyl, (C 2 -C 6 -alkenyloxyimino)-C 1 -C 6 -alkyl, (C 3 -C 6 -alkynyloxyimino)-C 1 -C 6 -alkyl, (benzyloxyimino)-C 1 -C 6 -alkyl, benzyloxy, —S-benzyl, benzylamino, phenoxy, —S-phenyl and phenylamino,
m is 0, 1, 2, 3, 4 or 5, and
each Y is independently selected from the group consisting of hydrogen, halogen, nitro, cyano, hydroxy, amino, —SH, —SF 5 , —CHO, —OCHO, —NHCHO, —COOH, —CONH 2 , —CONH(OH), —OCONH 2 , (hydroxyimino)-C 1 -C 6 -alkyl, 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 1 -C 8 -alkylamino, di-(C 1 -C 8 -alkyl)amino, wherein both alkyl residues may form a 4- to 7-membered heterocycle incorporating the nitrogen bonded to the phenyl system of the compound, C 1 -C 8 -alkoxy, C 1 -C 8 -halogenoalkoxy having 1 to 5 halogen atoms, C 2 -C 8 -alkenyloxy, C 2 -C 8 -halogenoalkenyloxy having 1 to 5 halogen atoms, C 3 -C 8 -alkynyloxy, C 3 -C 8 -halogenoalkynyloxy having 1 to 5 halogen atoms, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halogenocycloalkyl having 1 to 5 halogen atoms, C 1 -C 8 -alkylcarbonyl, C 1 -C 8 -halogenoalkylcarbonyl having 1 to 5 halogen atoms, —CONH(C 1 -C 8 -alkyl), —CON(C 1 -C 8 -alkyl) 2 , —CONH(OC 1 -C 8 -alkyl), —CON(C 1 -C 8 -alkyl)(C 1 -C 8 -alkyl), 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 -alkylcarbonylamino, C 1 -C 8 -halogenoalkylcarbonylamino having 1 to 5 halogen atoms, —OCONH(C 1 -C 8 -alkyl), —OCON(C 1 -C 8 -alkyl) 2 , —OCONH(OC 1 -C 8 -alkyl), —OCO(OC 1 -C 8 -alkyl), —S—C 1 -C 8 -alkyl, —S—C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 8 -alkyl, —S(O)—C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms, —S(O) 2 —C 1 -C 8 -alkyl, —S(O) 2 —C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms, —CH 2 —S—C 1 -C 8 -alkyl, —CH 2 —S(O)—C 1 -C 8 -alkyl, —CH 2 —S(O) 2 —C 1 -C 8 -alkyl, (C 1 -C 6 -alkoxyimino)-C 1 -C 6 -alkyl, (C 2 -C 6 -alkenyloxyimino)-C 1 -C 6 -alkyl, (C 3 -C 6 -alkynyloxyimino)-C 1 -C 6 -alkyl, (benzyloxyimino)-C 1 -C 6 -alkyl, benzyloxy, —S-benzyl, benzylamino, phenoxy, —S-phenyl and phenylamino, or
m is 2, 3, 4 or 5, and
at least two substituents Y are vicinal and, together with the carbon atoms to which they are bonded, form an annellated 5- or 6-membered carbocycle or a 5- or 6-membered heterocycle with one or two heteroatoms selected from the group consisting of oxygen and nitrogen, whereat two oxygen atoms are not directly connected, the carbocycle or heterocycle being independently substituted by 0 to 4 halogen atoms, 0 to 2 oxo-groups, 0 to 8 C 1 -C 8 -alkyl, 0 to 8 C 1 -C 8 -alkoxy or 0 to 4 C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms, and
the remaining substituents Y are independently selected from the group consisting of hydrogen, halogen, nitro, cyano, hydroxy, amino, —SH, —SF 5 , —CHO, —OCHO, —NHCHO, —COOH, —CONH 2 , —CONH(OH), —OCONH 2 , (hydroxyimino)-C 1 -C 6 -alkyl, 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 1 -C 8 -alkylamino, di-(C 1 -C 8 -alkyl)amino, C 1 -C 8 -alkoxy, C 1 -C 8 -halogenoalkoxy having 1 to 5 halogen atoms, C 2 -C 8 -alkenyloxy, C 2 -C 8 -halogenoalkenyloxy having 1 to 5 halogen atoms, C 3 -C 8 -alkynyloxy, C 3 -C 8 -halogenoalkynyloxy having 1 to 5 halogen atoms, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halogenocycloalkyl having 1 to 5 halogen atoms, C 1 -C 8 -alkylcarbonyl, C 1 -C 8 -halogenoalkylcarbonyl having 1 to 5 halogen atoms, —CONH(C 1 -C 8 -alkyl), —CON(C 1 -C 8 -alkyl) 2 , —CONH(OC 1 -C 8 -alkyl), —CON(OC 1 -C 8 -alkyl)(C 1 -C 8 -alkyl), 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 -alkylcarbonylamino, C 1 -C 8 -halogenoalkylcarbonylamino having 1 to 5 halogen atoms, —OCONH(C 1 -C 8 -alkyl), —OCON(C 1 -C 8 -alkyl) 2 , —OCONH(OC 1 -C 8 -alkyl), —OCO(OC 1 -C 8 -alkyl), —S—C 1 -C 8 -alkyl, —S—C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 8 -alkyl, —S(O)—C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms, —S(O) 2 —C 1 -C 8 -alkyl, —S(O) 2 —C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms, —CH 2 —S—C 1 -C 8 -alkyl, —CH 2 —S(O)—C 1 -C 8 -alkyl, —CH 2 —S(O) 2 —C 1 -C 8 -alkyl, (C 1 -C 6 -alkoxyimino)-C 1 -C 6 -alkyl, (C 2 -C 6 -alkenyloxyimino)-C 1 -C 6 -alkyl, (C 3 -C 6 -alkynyloxyimino)-C 1 -C 6 -alkyl, (benzyloxyimino)-C 1 -C 6 -alkyl, benzyloxy, —S-benzyl, benzylamino, phenoxy, —S-phenyl and phenylamino,
R 1 , R 2 , R 3 and R 4 are the same or different and are selected from the group consisting of hydrogen, halogen, cyano, hydroxy, amino, —SH, —CHO, —OCHO, —NHCHO, —COOH, —CONH 2 , —CONH(OH), —OCONH 2 , a (hydroxyimino)-C 1 -C 6 -alkyl group, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkylamino, di-(C 1 -C 6 -alkyl)amino, C 1 -C 6 -alkoxy, hydroxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 3 -alkyl, C 1 -C 6 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 6 -halogenoalkoxy having 1 to 5 halogen atoms, C 2 -C 6 -alkenyloxy, C 2 -C 6 -halogenoalkenyloxy having 1 to 5 halogen atoms, C 3 -C 6 -alkynyloxy, C 3 -C 6 -halogenoalkynyloxy having 1 to 5 halogen atoms, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halogenocycloalkyl having 1 to 5 halogen atoms, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, C 3 -C 6 -halogenocycloalkyl-C 1 -C 6 -alkyl having 1 to 5 halogen atoms, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -halogenoalkylcarbonyl having 1 to 5 halogen atoms, —CONH(C 1 -C 6 -alkyl), —CON(C 1 -C 6 -alkyl) 2 , —CONH(OC 1 -C 6 -alkyl), —CON(OC 1 -C 6 -alkyl)(C 1 -C 6 -alkyl), C 1 -C 6 -alkoxycarbonyl, a C 1 -C 6 -halogenoalkoxycarbonyl having 1 to 5 halogen atoms, —OC(O)—C 1 -C 6 -alkyl, —OC(O)—C 1 -C 6 -halogenoalkyl having 1 to 5 halogen atoms, —NHC(O)—C 1 -C 6 -alkyl, —NHC(O)—C 1 -C 6 -halogenoalkyl having 1 to 5 halogen atoms, —OCONH(C 1 -C

Assignees

• Bayer Animal Health Gmbh

Inventors

• Schwarz Hans-Georg
• Decor Anne
• Füβlein Martin
• Görgens Ulrich
• Ilg Kerstin
• Welz Claudia
• Lümmen Peter
• Köhler Adeline
• Börngen Kirsten

Classifications

• C07D405/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• A61P33/14

  Ectoparasiticides, e.g. scabicides · CPC title

• A61P33/00

  Antiparasitic agents · CPC title

• A01N43/40

  six-membered rings · CPC title

• C07D213/38

  having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom · CPC title