Cyclopentene and cyclopentadiene compounds for controlling invertebrate pests

Patent metadata

Field	Value
Publication number	US-2016355466-A1
Application number	US-201515114646-A
Country	US
Kind code	A1
Filing date	Feb 3, 2015
Priority date	Feb 3, 2014
Publication date	Dec 8, 2016
Grant date	—

Abstract

The present invention relates to cyclopent(adi)ene compounds of formula I

wherein the variables are as defined in the claims and description. The compounds are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes. The invention also relates to a method for controlling invertebrate pests by using these compounds and to plant propagation material and to an agricultural and a veterinary composition comprising said compounds.

First claim

1 - 27 . (canceled)

28 : A cyclopentene or cyclopentadiene compound of the formula (I)

wherein
the ring

is selected from following rings II-1 to II-3:

wherein
# is the attachment point to the ring with the ring members B 1 , B 2 and B 3 ; and
* is the attachment point to the ring with the ring members G 1 , G 2 , G 3 and G 4 ;

A is a group A 1 , A 2 or A 3 ;
wherein
A 1 is a group of following formula:

wherein
# denotes the attachment point to the remainder of the molecule;
W is selected from O and S;
Y is selected from hydrogen, —N(R 5 )R 6 and —OR 9 ;

A 2 is a group of following formula:

wherein
# denotes the attachment point to the remainder of the molecule;

A 3 is a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic ring containing 1, 2, 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO 2 , as ring members, or is a 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heterobicyclic ring containing 1, 2, 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO 2 , as ring members, where the heteromonocyclic or heterobicyclic ring is optionally substituted with one or more substituents R 1 ;

B 1 , B 2 and B 3 are each independently selected from the group consisting of N and CR 2 , with the proviso that at most two of B 1 , B 2 and B 3 are N;
G 1 , G 2 , G 3 and G 4 are each independently selected from the group consisting of N and CR 4 , with the proviso that at most two of G 1 , G 2 , G 3 and G 4 are N;
R 1 is selected from the group consisting of C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -haloalkoxy-C 1 -C 4 -alkyl-, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl and —C(═O)OR 15 ;
each R 2 is independently selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, —SCN, —SF 5 , C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, wherein the four last mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted by one or more radicals R 8 ,
—Si(R 12 ) 3 , —OR 9 , —S(O) n R 9 , —NR 10a R 10b ,
phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R 11 , and a 3-, 4-, 5-, 6-7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic or heterobicyclic ring containing 1, 2, 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO 2 , as ring members, where the heteromono- or heterobicyclic ring may be substituted by one or more radicals R 1l ;

R 3a , R 3b , R 3c , are each independently selected from the group consisting of hydrogen, halogen, hydroxyl, —CO 2 R 3d , C 1 -C 3 -alkyl, C 1 -C 3 -haloalkyl, C 2 -C 3 -alkenyl, C 2 -C 3 -alkynyl, C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkoxy, C 1 -C 3 -alkylthio, C 1 -C 3 -haloalkylthio, C 1 -C 3 -alkylsulfonyl and C 1 -C 3 -haloalkylsulfonyl; or
R 3a and R 3b together form a group ═O, ═C(R 3e ) 2 , ═NOH or ═NOCH 3 ;

R 3d is selected from the group consisting of hydrogen, C 1 -C 6 -alkyl and C 1 -C 3 -alkyloxy-C 1 -C 3 -alkyl-;
each R 3e is independently selected from the group consisting of hydrogen, halogen, CH 3 and CF 3 ;
each R 4 is independently selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, —SCN, —SF 5 , C 1 -C 6 -alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R 8 , C 3 -C 8 -cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R 8 , C 2 -C 6 -alkenyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R 8 , C 2 -C 6 -alkynyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R 8 ,
—Si(R 12 ) 3 , —OR 9 , —S(O) n R 9 , —NR 10a R 10b ,
phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R 11 , and a 3-, 4-, 5-, 6-7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic or heterobicyclic ring containing 1, 2, 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO 2 , as ring members, where the heteromonocyclic or heterobicyclic ring may be substituted by one or more radicals R 11 ;
each R 5 is independently selected from the group consisting of hydrogen, cyano, C 1 -C 10 -alkyl, C 3 -C 8 -cycloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted with one or more substituents R 8 ; and —S(O) n R 9 ,
each R 6 is independently selected from the group consisting of hydrogen, cyano, C 1 -C 10 -alkyl, C 3 -C 8 -cycloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted by one or more substituents R 8 , —OR 9 , —NR 10a R 10b , —S(O) n R 9 , —C(═O)NR 10a N(R 10a )R 10b , —Si(R 12 ) 3 , —C(═O)R 8 , —CH═NOR 9 ,
phenyl which may be substituted with 1, 2, 3, 4, or 5 substituents R 11 , and a 3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic or heterobicyclic ring containing 1, 2, 3 or 4 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO 2 , as ring members, where the heteromonocyclic or heterobicyclic ring may be substituted with one or more substituents R 11 ;
or R 5 and R 6 , together with the nitrogen atom to which they are bound, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring, where the ring may further contain 1, 2, 3 or 4 heteroatoms or heteroatom-containing groups selected from O, S, N, SO, SO 2 , C═O and C═S as ring members, wherein the heterocyclic ring may be substituted with 1, 2, 3, 4 or 5 substituents independently selected from the group consisting of halogen, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, wherein the aliphatic or cycloaliphatic moieties in the twelve last-mentioned radicals may be substituted by one or more radicals R 8 , and phenyl which may be substituted with 1, 2, 3, 4 or 5 substituents R 11 ;
or R 5 and R 6 together form a group ═C(R 8 ) 2 , ═S(O) m (R 9 ) 2 , ═NR 10a or ═NOR 9 ;

R 7a , R 7b are each independently selected from the group consisting of hydrogen, halogen, cyano, C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkyl, C 2 -C 6 -alkenyl and C 2 -C 6 -alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or

Assignees

• Basf Se

Inventors

• Bindschaedler Pascal
• Von Deyn Wolfgang
• Narine Arun
• KOERBER Karsten `
• Braun Franz-Josef

Classifications

• A61P33/14

  Ectoparasiticides, e.g. scabicides · CPC title

• A61P33/00

  Antiparasitic agents · CPC title

• C07D239/42

  One nitrogen atom (nitro radicals C07D239/30) · CPC title

• C07C2601/10

  the ring being unsaturated · CPC title

• C07D213/75

  Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates · CPC title