Pesticidal and parasiticidal vinyl isoxazoline compounds

Patent metadata

Field	Value
Publication number	US-10653144-B2
Application number	US-201716340795-A
Country	US
Kind code	B2
Filing date	Oct 11, 2017
Priority date	Oct 14, 2016
Publication date	May 19, 2020
Grant date	May 19, 2020

Abstract

The present invention relates to pesticidal and parasiticidal isoxazoline of formula (I) and salts thereof:

wherein variables B 1 , B 2 , B 3 , R 1 , P 1 , P 2 , Y and Q are described herein are as defined in the description. The invention also relates to parasiticidal and pesticidal compositions comprising the isoxazoline compounds of formula (I), processes for their preparation and their uses to prevent or treat parasitic infections or infestations in animals and as pesticides.

First claim

What is claimed is:

1. A pesticidal isoxazoline compound of formula (I):

wherein:
the asterisk (*) signifies a chiral quaternary center;
the squiggly bond ( ) signifies that the double bond may be in the cis- or trans-configuration with respect to P 1 and P 2 ;
B 1 , B 2 and B 3 are each independently C—R or N;

each R is independently H, halogen, cyano, —NO 2 , alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, —SF 5 , —C(═S)—NH 2 , alkylamino, dialkylamino or alkoxycarbonyl;
R 1 is C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;
P 1 and P 2 are independently hydrogen, halogen, cyano, nitro, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl or haloalkylsulfonyl;
Y is Y-2, Y-4, Y-5 or Y-6:

wherein Z, Z 1 , Z 2 , Z 3 , Z 4 , Z 5 and Z 6 are independently C—H or N, and wherein R 10 and R 11 are independently H, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;
Q is X—NR 2 R 3 , OH, NH 2 , alkoxy, haloalkoxy, alkylamino, haloalkylamino, dialkylamino, dihaloalkylamino, thiol, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, —SF 5 , —C(═S)—NH 2 , or an optionally substituted 5- or 6-membered carbocyclyl, heterocyclyl, heteroaryl ring, wherein the optional substituents of said carbocyclyl, heterocyclyl or heteroaryl ring are selected from halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkylamino, dialkylamino, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, —SF 5 , —CN, —NO 2 and —C(═S)—NH 2 ; or the groups T1 or T2:

or
Y is Y-3 wherein Q is (—CH 2 —)(—CH 2 —)N—R 3

W is O or S;
X is (CH 2 ) n , CH(CH 3 ), CH(CN), C(═O) or C(═S);
R 2 is H, alkyl, alkenyl, alkynyl, cycloalkyl, alkylcycloalkyl, cycloalkylalkyl, alkylcarbonyl or alkoxycarbonyl;
R 3 is H, OR 7 , NR 8 R 9 or Q 1 ; or alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, alkylcycloalkyl, cycloalkylalkyl, alkylcarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl or dialkylaminocarbonyl, each optionally substituted with one or more substituents independently selected from R 4 ; or
when Q is X—NR 2 R 3 , R 2 and R 3 taken together with the nitrogen to which they are attached to form a ring containing 2 to 6 atoms of carbon and optionally one additional atom selected from the group consisting of N, S and O, said ring optionally substituted with 1 to 4 substituents independently selected from the group consisting of alkyl, halogen, —CN, —NO 2 and alkoxy;
each R 4 is independently halogen; alkyl, cycloalkyl, alkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkylamino, haloalkylamino, dialkylamino, dihaloalkylamino, cycloalkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, haloalkylcarbonyl, haloalkoxycarbonyl, haloalkylaminocarbonyl, dihaloalkylaminocarbonyl, hydroxy, —SF 5 , —C(═S)NH 2 , —NH 2 , —CN or —NO 2 ; or Q 2 ;
each R 5 is independently halogen, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkylamino, dialkylamino, alkoxycarbonyl, —SF 5 , —C(═S)NH 2 , —CN or —NO 2 ;
each R 6 is independently halogen, alkyl, haloalkyl, cycloalkyl, halocycloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkylamino, dialkylamino, —SF 5 , —C(═S)NH 2 , —CN, —NO 2 , phenyl or pyridinyl;
R 7 is H; or alkyl, alkenyl, alkynyl, cycloalkyl, alkylcycloalkyl or cycloalkylalkyl, each optionally substituted with one or more halogens;
R 8 is H, alkyl, alkenyl, alkynyl, cycloalkyl, alkylcycloalkyl, cycloalkylalkyl, alkylcarbonyl or alkoxycarbonyl;
R 9 is H; Q 3 ; or alkyl, alkenyl, alkynyl, cycloalkyl, alkylcycloalkyl or cycloalkylalkyl, each optionally substituted with one or more substituents independently selected from R 4 ; or
R 8 and R 9 taken together with the nitrogen to which they are attached form a ring containing 2 to 6 atoms of carbon and optionally one additional atom selected from the group consisting of N, S and O, said ring optionally substituted with 1 to 4 substituents independently selected from the group consisting of alkyl, halogen, —CN, —NO 2 and alkoxy;
Q 1 is a phenyl ring, a 5- or 6-membered heterocyclic ring, or an 8-, 9- or 10-membered fused bicyclic ring system optionally containing one to three heteroatoms selected from up to 1 O, up to 1 S and up to 3 N, each ring or ring system optionally substituted with one or more substituents independently selected from R 5 ;
Q 2 is independently a phenyl ring or a 5- or 6-membered heterocyclic ring, each ring optionally substituted with one or more substituents independently selected from R 6 ;
Q 3 is a phenyl ring or a 5- or 6-membered heterocyclic ring, each ring optionally substituted with one or more substituents independently selected from R 6 ; and

n is 0, 1 or 2.

2. The pesticidal isoxazoline compound of claim 1 , wherein B 1 , B 2 and B 3 are each independently C—R; and R is H, halogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio or SF 5 .

3. The pesticidal isoxazoline compound of claim 1 , wherein one or two of B 1 , B 2 and B 3 are each N and the others of B 1 , B 2 and B 3 are C—R; and R is H, halogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio or SF 5 .

4. The pesticidal isoxazoline compound of any of claim 1 , 2 or 3 , wherein R 1 is CF 3 .

5. The pesticidal isoxazoline compound of claim 1 , wherein Y is Y-2:

wherein Z 1 , Z 2 , Z 3 , Z 4 , Z 5 and Z 6 are CH or N, provided at at most 3 of Z 1 , Z 2 , Z 3 , Z 4 , Z 5 and Z 6 are N.

6. The pesticidal isoxazoline compound of claim 1 , wherein Y is Y-4:

wherein Z is N or CH.

7. The pesticidal isoxazoline compound of claim 1 , wherein Y is Y-5:

8. The pesticidal isoxazoline compound of claim 1 , wherein Y is Y-3:

and
Q is group (—CH 2 —)(—CH 2 —)N—R 3 .

9. The pesticidal isoxazoline compound of claim 1 , wherein y is Y-6:

wherein R 10 and R 11 are independently H, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl.

10. The pesticidal isoxazoline compound of claim 1 , wherein:
Q is X—NR 2 R 3 ;
R 2 is H or C 1 -C 3 alkyl; and
R 3 is C 1 -C 3 a

Assignees

• Boehringer Ingelheim Animal Health Usa Inc

Inventors

• Long Alan
• Le Hir De Fallois Loic Patrick

Classifications

• A61P33/14

  Ectoparasiticides, e.g. scabicides · 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

• A01N43/90

  having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system · CPC title

• C07B2200/07

  Optical isomers · CPC title

• C07D471/04

  Ortho-condensed systems · CPC title