Bicyclyl-Substituted Isothiazoline Compounds

Patent metadata

Field	Value
Publication number	US-2016145223-A1
Application number	US-201414900210-A
Country	US
Kind code	A1
Filing date	Jun 23, 2014
Priority date	Jun 24, 2013
Publication date	May 26, 2016
Grant date	—

Abstract

The present invention relates to bicyclyl-substituted isothiazoline 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 - 30 . (canceled)

31 . An isothiazoline compound of the formula I

wherein
A is a group A 1 , A 2 , A 3 or A 4 ;
wherein
A 1 is selected from the group consisting of —C(═NR 6 )R 8 , —S(O) n R 9 , —N(R 5 )R 6 and —CN;
A 2 is a group of following formula:

wherein
# denotes the bond to the aromatic ring of formula (I);
W is selected from the group consisting of O and S;
Y is selected from the group consisting of hydrogen, —N(R 5 )R 6 and —OR 9 ;

A 3 is a group of following formula:

wherein
# denotes the bond to the aromatic ring of formula (I);

A 4 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 the group consisting of 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 the group consisting of 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 and G 2 are each independently selected from the group consisting of N and CR 4 , with the proviso that at most one of G 1 and G 2 is N;
R g1 and R g2 form together a bridging group selected from the group consisting of —CH 2 CH 2 CH 2 CH 2 —, —CH 2 CH 2 CH═CH—, —CH 2 CH═CH—CH 2 —, —NR 10a CH 2 CH 2 CH 2 —, —CH 2 NR 10a CH 2 CH 2 —, —NR 10a NR 10a CH 2 CH 2 —, —NR 10a CH 2 NR 10a CH 2 —, —NR 10a CH 2 CH 2 NR 10a —, —N═CH—CH═CH—, —CH═N—CH═CH—, —N═CH—N═CH—, —N═CH—CH═N—, —OCH 2 CH 2 CH 2 —, —CH 2 OCH 2 CH 2 —, —OCH 2 CH 2 O—, —OCH 2 OCH 2 —, —OCH═CHCH 2 —, —S(O) n CH 2 CH 2 CH 2 —, —CH 2 S(O) n CH 2 CH 2 —, —S(O) n CH 2 CH 2 S(O) n —, —S(O) n CH 2 S(O) n CH 2 —, —S(O) n CH═CHCH 2 —, —CH 2 CH 2 CH 2 —, —CH═CHCH 2 —, —CH 2 CH 2 O—, —CH 2 OCH 2 —, —O(CH 2 )O—, —CH═CHO—, —CH 2 C(═O)O—, —C(═O)OCH 2 —, —CH 2 CH 2 S(O) n —, —CH 2 S(O) n CH 2 —, —S(O) n CH 2 S(O) n —, —CH═CH 2 S(O) n —, —CH 2 C(═S)S—, —C(═S)SCH 2 —, —CH 2 CH 2 NR 10a —, —CH 2 NR 10a CH 2 —, —NR 10a NR 10a CH 2 —, —NR 10a CH 2 NR 10a , —CH 2 CH═N—, —CH═CH—NR 10a —, —CH═N—NR 10a —, —N═CH—NR 10a —, —OCH═N—, —S(O) n CH═N—, —N═N—NR 10a —, ═CH—O—CH═, ═CH—S(O) n —CH═, ═CH—NR 10a —CH═, ═N—S(O) n —N═ and ═N—NR 10a —N═ (where in case of the five last groups, in the structural formula, there is formally no double bond between the two carbon atoms carrying the radicals R g1 and R g2 ); where the hydrogen atoms of the above groups may be replaced by one or more substituents selected from the group consisting of halogen, methyl, halogenated methyl, hydroxyl, methoxy and halogenated methoxy; and/or one or two CH 2 groups of the above groups may be replaced by a C═O group;
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 5 -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 the group consisting of 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 11 ;
R 3a , R 3b 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 3c ) 2 , ═NOH or ═NOCH 3 ;

each R 3C is independently selected from the group consisting of hydrogen, halogen, CH 3 and CF 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 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 5 -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 the group consisting of 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 5 -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 5 -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 the group consisting of 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 t

Assignees

• Basf Se

Inventors

• Bindschaedler Pascal
• Von Deyn Wolfgang
• Koerber Karsten
• Culbertson Deborah L
• Braun Franz Josef
• Gunjima Koshi

Classifications

• C07D417/12

  linked by a chain containing hetero atoms as chain links · CPC title

• A01N43/80

  five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2 · CPC title

• C07D275/02 Primary

  not condensed with other rings · CPC title

• A61P33/00

  Antiparasitic agents · CPC title