Pesticidal and parasiticidal pyrazole-isoxazoline compounds

Patent metadata

Field	Value
Publication number	US-11589586-B2
Application number	US-201816638957-A
Country	US
Kind code	B2
Filing date	Aug 14, 2018
Priority date	Aug 14, 2017
Publication date	Feb 28, 2023
Grant date	Feb 28, 2023

Abstract

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

wherein variables R 1 , P, 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):

or a pharmaceutically or agriculturally acceptable salt thereof, wherein:
the asterisk (*) signifies a quaternary center;
P is an optionally substituted pyrazole ring;
R 1 is alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, alkylcycloalkyl or cycloalkylalkyl, each optionally substituted with one or more substituents independently selected from R 6 ;
Y is an optionally substituted phenylene, naphthylene, indanylene, a 5- or 6-membered heteroarylene, an 8-12-membered heterobicyclylene or an 8-12-membered heterotricyclylene, each optionally independently substituted by one or more R 7 ;
Q is X—NR 5 R 6 , —NR 5 R 6 , X—R 6 , 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 or the groups T1 or T2:

wherein W is O or S;
X is (CH 2 )n, CH(CH 3 ), CH(CN), C(═O) or C(═S);
R 5 is H, alkyl, alkenyl, alkynyl, cycloalkyl, alkylcycloalkyl, cycloalkylalkyl, alkylcarbonyl or alkoxycarbonyl;
R 6 is H, OR 10 , NR 11 , R 12 or Q 1 ; 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 7 ; or
R 5 and R 6 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 7 is independently halogen; alkyl, cycloalkyl, alkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkyl sulfonyl, 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 8 is independently halogen, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkyl sulfonyl, haloalkylsulfonyl, alkylamino, dialkylamino, alkoxycarbonyl, —SF 5 , —C(═S)NH 2 , —CN or —NO 2 ;
each R 9 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 10 is H; or alkyl, alkenyl, alkynyl, cycloalkyl, alkylcycloalkyl or cycloalkylalkyl, each optionally substituted with one of more halogen;
R 11 is H, alkyl, alkenyl, alkynyl, cycloalkyl, alkylcycloalkyl, cycloalkylalkyl, alkylcarbonyl or alkoxycarbonyl;
R 12 is H; Q 3 ; or alkyl, alkenyl, alkynyl, cycloalkyl, alkylcycloalkyl or cycloalkylalkyl, each optionally substituted with one or more substituents independently selected from R 7 ; or
R 11 and R 12 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;
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 8 ;
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 9 ;
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 9 ; and n is 0, 1 or 2.

2. The pesticidal isoxazoline compound of claim 1 , wherein P is P 1 , P 2 , P 3 or P 4 :

wherein, R 2 and R 3 are independently H, halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkoxy, haloalkoxy, alkoxyalkyl, alkoxyalkoxyalkyl, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, amino, alkylamino, dialkylamino, haloalkylamino, dihaloalkylamino, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aryl, heteroaryl, arylalkyl, heteroarylalkyl, SF 5 , —CN, —NO 2 or —C(S)NH 2 , wherein each alkyl, cycloalkyl, alkenyl, alkynyl, aryl or heteroaryl is optionally independently substituted by one or more R 7 ;
R 4 is H, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, arylalkyl, heteroarylalkyl, alkoxyalkyl, alkoxyalkoxyalkyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, alkylsulfinyl, haloalkylsulfinyl, alkyl sulfonyl, haloalkylsulfonyl, aryl, heteroaryl, arylalkyl or heteroarylalkyl, wherein each optionally substituted by one or more R 7 .

3. The pesticidal isoxazoline compound of claim 1 , wherein Y is Y-1, Y-2, Y-3, Y-4, Y-5 or Y-6:

wherein Z 1 , Z 2 , Z 3 , Z 4 , Z 5 and Z 6 are independently N or C—R 15 and wherein at most 3 Z groups are nitrogen;
Z is N or C-R 15 ; and
R 13 and R 15 are independently 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, C 1 -C 3 alkylsulfinyl, C 1 -C 3 haloalkylsulfinyl, C 1 -C 3 alkylsulfonyl, C 1 -C 3 haloalkylsulfonyl, —CN, —NO 2 or —SF 5 .

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

5. The pesticidal isoxazoline compound of claim 2 , wherein R 2 and R 3 are independently hydrogen, methyl or CF 3 ; and R 4 is hydrogen or C 1 -C 3 -alkyl.

6. The pesticidal isoxazoline compound of claim 3 wherein:
Y is Y-2, Y-3, Y-5 or Y-6;
Z 1 , Z 2 , Z 3 , Z 4 , Z 5 or Z 6 are independently N or C—H;
Z is N or C—H; and
each R 13 is H or C 1 -C 3 alkyl.

7. The pesticidal isoxazoline compound of claim 1 , wherein Q is X—NR 5 R 6 .

8. The pesticidal isoxazoline compound of claim 7 , wherein R 5 is H, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl; and R 6 is C 3 -C 8 cycloalkyl, haloalkyl or alkyl optionally substituted by one or more R 7 .

9. The pesticidal isoxazoline compound of claim 7 , wherein Q is —C(O)NHCF 3 , —C(O)NHCH 2 CH 2 CF 3 , —C(O)NHCH 2 CF 3 , —C(O)NHCH 2 C(O)NHCH 2 CF 3 , —C(O) NHCH 2 CH 2 S(O) n CH 3 where n is 0, 1 or 2 or —C(O)CH 2 S(O) n CH 3 where n is 0, 1 or 2.

10. The pesticidal isoxazoline compound of claim 7 , wherein R 5 is H or C 1 -C 3 alkyl; and R 6 is cyclopropyl, cyclob

Assignees

• Boehringer Ingelheim Animal Health Usa Inc

Inventors

• Long Alan
• Lee Hyoung Ik

Classifications

• C07D493/10

  Spiro-condensed systems · CPC title

• C07D491/107

  with only one oxygen atom as ring hetero atom in the oxygen-containing ring · CPC title

• A61P33/00

  Antiparasitic agents · CPC title

• C07D413/04 Primary

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

• A01N43/90

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