Naphthyl- or isoquinolinyl-substituted isothiazoline compounds

Patent metadata

Field	Value
Publication number	US-2016374342-A1
Application number	US-201414757414-A
Country	US
Kind code	A1
Filing date	Jun 23, 2014
Priority date	Jun 24, 2013
Publication date	Dec 29, 2016
Grant date	—

Abstract

The present invention relates to naphthyl- or isoquinolinyl-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

We claim:

1 . Isothiazoline compounds of the formula I

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

wherein
# denotes the bond to the remainder of the molecule;
W is selected from O and S;

A 3 is a group of following formula:

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

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 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 , and —NR 10a R 10b ;

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 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 , and —NR 10a R 10b ;

each R 5 is independently selected from the group consisting of hydrogen, 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 ,
R 6a is selected from —X—R 6b and —N(R 5a )R 6c ; wherein
X is selected from —C(R a ) 2 —, —C(R a ) 2 —C(R a ) 2 —, —C(R a ) 2 —C(═O)—NR 10a —C(R a ) 2 —, —C(R a ) 2 C(R a ) 2 —C(═O)—NR 10a C(R a ) 2 —, —C(R a ) 2 S(O) n —C(R a ) 2 —, —C(R a ) 2 —C(R a ) 2 —S(O) n —C(R a ) 2 —, —C(R a ) 2 —O—C(R a ) 2 —, and
—C(R a ) 2 —C(R a ) 2 —O—C(R a ) 2 —, wherein
each R a is independently selected from the group consisting of hydrogen, halogen, C 1 -C 3 -alkyl, and C 1 -C 3 -haloalkyl;

R 5a has independently one of the meanings given for R 5 ;
R 6b is selected from the group consisting of C 3 -C 8 -cycloalkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, wherein the three last-mentioned radicals may be partially or fully halogenated and/or may be substituted by one or more substituents R 8 ; and
R 6c is selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, 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, where the aliphatic and cycloaliphatic moieties in the eight last-mentioned radicals may be substituted by one or more radicals R 13 ;
—C 1 -C 6 -alkyl-C(═O)OR 15 , —C 1 -C 6 -alkyl-C(═O)N(R 14a )R 14b , —C 1 -C 6 -alkyl-C(═S)N(R 14a )R 14b , —C 1 -C 6 -alkyl-C(═NR 14 )N(R 14a )R 14b , C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, —S(O) n R 15 , —S(O) n N(R 14a )R 14b , —C(═O)R 13 , —C(═O)OR 15 , —C(═O)N(R 14a )R 14b , —C(═S)R 13 , —C(═S)SR 15 , —C(═S)N(R 14a )R 14b , and —C(═NR 14 )R 13 ;

where in case that R 5 is hydrogen, R 6a is further selected from hydrogen, 1-cyanocyclopropyl, 1-cyanocyclobutyl and 1-cyanopentyl; or
R 5 and R 6a form together a group ═S(O) m (R 9 ) 2 ;

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 , 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 or R 5 and R 6a , 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 ;

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 may be substituted by one or more radicals R 8 ;
each R 8 is independently selected from the group consisting of cyano, azido, nitro, —SCN, —SF 5 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 3 -C 8 -cycloalkenyl, C 3 -C 8 -halocycloalkenyl, where the cycloaliphatic moieties in the four last-mentioned radicals may be substituted by one or mor

Assignees

• Merial Inc

Inventors

• Bindschädler Pascal
• Von Deyn Wolfgang
• Körber Karsten
• Culbertson Deborah L
• Gunjima Koshi
• Braun Franz Josef

Classifications

• A61P33/10

  Anthelmintics · CPC title

• A61P33/00

  Antiparasitic agents · CPC title

• A01N47/30

  Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl · CPC title

• A01N43/80 Primary

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

• C07D275/02

  not condensed with other rings · CPC title