Antiparisitic and pesticidal isoxazoline compounds
The present invention relates to novel and inventive isoxazoline of formula (I) and salts thereof: wherein variables D 1 , D 2 , D 3 , D 4 , D 5 , R 1 , B 1 , B 2 , B 3 , R 2 , R 3 , R 4 , R 5 , R 6 , Y, Z, L, a and b 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.
1. A parasiticidal and pesticidal isoxazoline compound of formula (I):
wherein:
each of D 1 , D 2 , D 3 , D 4 and D 5 are independently N or C-A 1 , C-A 2 , C-A 3 , C-A 4 and C-A 5 , respectively, with the proviso that at most only three of D 1 , D 2 , D 3 , D 4 and D 5 may be simultaneously N;
R 1 is halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl or cycloalkylalkyl, each which is unsubstituted or substituted with one or more of hydroxy, amino, alkyl- or di(alkyl)amino, alkoxy, haloalkoxy, alkylthio or haloalkylthio;
A 1 , A 2 , A 3 , A 4 and A 5 are independently hydrogen, halogen, hydroxy, amino, alkyl- or di(alkyl)amino, alkyl, cycloalkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, —CN or —NO 2 ;
B 1 , B 2 and B 3 are independently N or C—X;
each X is independently hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, amino, alkylamino, haloalkylamino, dialkylamino, dihaloalkylamino, hydroxyalkyl, alkoxyalkyl, alkyl substituted by thiol or alkylthioalkyl, —CN or —NO 2 ; or two adjacent X together form a 5- or 6-membered ring together with the carbon atoms to which they are bonded by forming —CH 2 CH 2 CH 2 —, —CH═CH—CH═CH—, —CH 2 CH 2 O—, —CH 2 OCH 2 —, —OCH 2 O—, —CH 2 CH 2 S—, —CH 2 SCH 2 —, —SCH 2 S—, —CH 2 CH 2 CH 2 CH 2 —, —CH 2 CH 2 CH 2 O—, —CH 2 CH 2 OCH 2 —, —CH 2 OCH 2 O—, —OCH 2 CH 2 O—, —OCH 2 CH 2 S—, —SCH 2 CH 2 S—, —OCH═N— or —SCH═N—,
R 2 is hydrogen, halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, hydroxy, alkoxy, amino, alkyl- or dialkylamino, —CN or —NO 2 ;
R 3 , R 4 , R 5 and R 6 are each independently hydrogen, halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, amino, alkylamino, haloalkylamino, dialkylamino, dihaloalkylamino, hydroxyalkyl, alkoxyalkyl, alkyl substituted by thiol or alkylthioalkyl; or
R 5 and R 6 together with the carbon atom to which they are bonded together form C═W, with the proviso that at least one of R 5 and R 6 together form the group C═W;
R 7 and R 8 are independently hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, aryl, heteroaryl, heterocyclyl, alkyl substituted by thiol, haloalkyl substituted by thiol, alkylthioalkyl, hydroxyalkyl or alkoxyalkyl;
Y is hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, alkylcycloalkyl, cycloalkylalkyl, aryl, heterocyclyl or heteroaryl each of which is unsubstituted or substituted with one or more of halogen, hydroxy, amino, alkyl- or di(alkyl)amino, alkyl, cycloalkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, R 7 S(O)—, R 7 S(O) 2 —, R 7 C(O)—, R 7 R 8 NC(O)—, R 7 OC(O)—, R 7 C(O)O—, R 7 C(O)NR 8 — or —CN; or Y is Y-1, Y-2, Y-3, Y-4, Y-5, Y-6, Y-7, Y-8, Y-9, Y-10, Y-11, Y-12 or Y-13, wherein # signifies the point of attachment;
wherein each R 9 , R 10 are independently hydrogen, alkyl, haloalkyl, alkyl substituted by thiol, alkylthioalkyl, hydroxyalkyl, alkoxylakyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, aryl, heteroaryl, heterocyclyl, R 7 S(O)—, R 7 S(O) 2 —, R 7 C(O)—, R 7 R 8 NC(O)—, R 7 OC(O)—, R 7 C(O)O—, R 7 C(O)NR 8 —;
each R 11 is independently hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, amino, alkylamino, haloalkylamino, dialkylamino, dihaloalkylamino, hydroxyalkyl, alkoxyalkyl, alkyl substituted by thiol or alkylthioalkyl;
each R 12 and R 13 is independently hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, amino, alkylamino, haloalkylamino, dialkylamino, dihaloalkylamino, hydroxyalkyl, alkoxyalkyl, alkyl substituted by thiol or alkylthioalkyl; or
R 12 and R 13 together with the carbon atom to which they are bonded together form C═W;
W, W 1 and Z are independently O, S or NR 7 ;
L is a direct bond, —CR 3 R 4 —, —NR 8 — or —O—;
a is 1, 2 or 3;
b is 2 or 3;
n is 1, 2, 3 or 4; and
m is 0, 1 or 2.
2. The isoxazoline compound of claim 1 , wherein D 1 , D 2 , D 3 , D 4 and D 5 are each respectively C-A 1 , C-A 2 , C-A 3 , C-A 4 and C-A 5 .
3. The isoxazoline compound of claim 1 , wherein B 1 , B 2 and B 3 are C—H.
4. The isoxazoline compound of claim 1 , wherein B 1 and B 2 are C—X wherein the two Xs together form a 5- or 6-membered ring together with the carbon atoms to which they are bonded by forming —CH 2 CH 2 CH 2 —, —CH═CH—CH═CH—, —CH 2 CH 2 O—, —CH 2 OCH 2 —, —OCH 2 O—, —CH 2 CH 2 S—, —CH 2 SCH 2 —, —SCH 2 S—, —CH 2 CH 2 CH 2 CH 2 —, —CH 2 CH 2 CH 2 O—, —CH 2 CH 2 OCH 2 —, —CH 2 OCH 2 O—, —OCH 2 CH 2 O—, —OCH 2 CH 2 S—, —SCH 2 CH 2 S—, —OCH═N— or —SCH═N—.
5. The isoxazoline compound of claim 4 , wherein the two Xs together form —CH═CH—CH═CH— to form a naphthalene ring together with the carbon atoms to which they are bonded.
6. The isoxazoline compound of claim 1 , wherein D 1 , D 2 , D 3 , D 4 and D 5 are respectively C-A 1 , C-A 2 , C-A 3 , C-A 4 and C-A 5 ; A 2 , A 4 and A 5 are hydrogen; and A 1 and A 3 are independently halogen, alkyl or haloalkyl.
7. The isoxazoline compound of claim 1 , wherein the compound has the structure of formula (IA):
wherein:
R 1 is halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl or cycloalkylalkyl, each which is unsubstituted or substituted with one or more of hydroxy, amino, alkyl- or di(alkyl)amino, alkoxy, haloalkoxy, alkylthio or haloalkylthio;
A 1 and A 3 are independently hydrogen, halogen, hydroxy, amino, alkyl- or di(alkyl)amino, alkyl, cycloalkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, —CN or —NO 2 ;
B 1 and B 2 are independently N or C—X;
each X is independently hydrogen, halogen, alkyl or haloalkyl; or two adjacent X together form a 5- or 6-membered ring together with the carbon atoms to which they are bonded by forming —CH 2 CH 2 CH 2 —, —CH═CH—CH═CH—, —CH 2 CH 2 O—, —CH 2 OCH 2 —, —OCH 2 O—, —CH 2 CH 2 S—, —CH 2 SCH 2 —, —SCH 2 S—, —CH 2 CH 2 CH 2 CH 2 —, —CH 2 CH 2 CH 2 O—, —CH 2 CH 2 OCH 2 —, —CH 2 OCH 2 O—, —OCH 2 CH 2 O—, —OCH 2 CH 2 S—, —SCH 2 CH 2 S—, —OCH═N— or —SCH═N—;
R 2 is hydrogen, halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, hydroxy, alkoxy, amino, alkyl- or dialkylamino, —CN or —NO 2 ;
R 3 , R 4 , R 5 and R 6 are each independently hydrogen, halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, amino, alkylamino, haloalkylamino, dialkylamino, dihaloalkylamino, hydroxyalkyl, alkoxyalkyl, alkyl substituted by thiol or alkylthioalkyl; or
R 5 and R 6 together with the carbon atom to which they are bonded together form C═W, with the proviso that at least one of R 5 and R 6 together form the group C═W;
R 7 and R 8 are independently hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, aryl, heteroaryl, heterocyclyl, alkyl substituted by thiol, haloalkyl substituted by thiol, alkylthioalkyl, hydroxyalkyl or alkoxyalkyl;
Y is hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, alkylcycloalkyl, cycloalkylalkyl, aryl, heterocyclyl or heteroaryl each of which is unsubstituted or substituted with one or more of halogen, hydroxy, amino, alkyl- or di(alkyl)amino, alkyl, cycloalkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, R 7 S(O)—, R 7 S(O) 2 —, R 7 C(O)—, R 7 R 8 NC(O)—, R 7 OC(O)—, R 7 C(O)O—, R 7 C(O)NR 8 —, —CN or —NO 2 ; or Y is Y-1, Y-2, Y-3, Y-4, Y-5, Y-6, Y-7, Y-8, Y-9, Y-10, Y-11, Y-12 or Y-13, wherein # signifies the point of attachment;
wherein each R 9 , R 10 are independently hydrogen, alkyl, haloalkyl, alkyl substituted by thiol, alkylthioalkyl, hydroxyalkyl, alkoxylakyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, aryl, heteroaryl, heterocyclyl, R 7 S(O)—, R 7 S(O) 2 —, R 7 C(O)—, R 7 R 8 NC(O)—, R 7 OC(O)—, R 7 C(O)O—, R 7 C(O)NR 8 —;
each R 11 is independently hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, amino, alkylamino, haloalkylamino, dialkylamino, dihaloalkylamino, hydroxyalkyl, alkoxyalkyl, alkyl substituted by thiol or alkylthioalkyl;
each R 12 and R 13 is independently hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, amino, alkylamino, haloalkylamino, dialkylamino, dihaloalkylamino, hydroxyalkyl, alkoxyalkyl, alkyl substituted by thiol or alkylthioalkyl; or
R 12 and R 13 together with the carbon atom to which they are bonded together form C═W;
W, W 1 and Z are independently O, S or NR′;
L is a direct bond, —CR 3 R 4 —, —NR 8 — or —O—;
a is 1, 2 or 3;
b is 2 or 3;
n is 1, 2, 3 or 4; and
m is 0, 1 or 2.
8. An isoxazoline compound of formula (IB):
wherein:
R 1 is alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl;
A 1 and A 3 are independently hydrogen, halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl or haloalkynyl;
B 1 and B 2 are independently N or C—X;
each X is independently hydrogen, halogen, alkyl or haloalkyl; or two adjacent X together form a 5- or 6-membered ring together with the carbon atoms to which they are bonded by forming —CH 2 CH 2 CH 2 —, —CH═CH—CH═CH—, —CH 2 CH 2 O— —CH 2 OCH 2 —, —OCH 2 O—, —CH 2 CH 2 S—, —CH 2 SCH 2 —, —SCH 2 S—, —CH 2 CH 2 CH 2 CH 2 —, —CH 2 CH 2 CH 2 O—, —CH 2 CH 2 OCH 2 —, —CH 2 OCH 2 O—, —OCH 2 CH 2 O—, —OCH 2 CH 2 S—, —SCH 2 CH 2 S—, —OCH═N— or —SCH═N—;
R 2 is hydrogen, halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl or haloalkynyl;
R 3 , R 4 , R 3′ , R 4′ , R 5 , R 6 , R 5′ and R 6′ are each independently hydrogen, halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl or haloalkynyl; or
R 3 and R 4 and/or R 3′ and R 4′ together with the carbon atom to which they are bonded together form C═W; and/or
R 5 and R 6 and/or R 5′ and R 6′ together with the carbon atom to which they are bonded together form C═W, with the proviso that at least one of R 3 and R 4 , R 3′ and R 4′ , R 5 and R 6 , or R 5′ and R 6′ , together with the carbon atom to which they are attached form the group C═W;
R 7 and R 8 are independently hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, aryl, heteroaryl, heterocyclyl, alkyl substituted by thiol, haloalkyl substituted by thiol, alkylthioalkyl, hydroxyalkyl or alkoxyalkyl;
Y is hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, alkylcycloalkyl, cycloalkylalkyl, aryl, heterocyclyl or heteroaryl each of which is unsubstituted or substituted with one or more of halogen, hydroxy, amino, alkyl- or di(alkyl)amino, alkyl, cycloalkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, R 7 S(O)—, R 7 S(O) 2 —, R 7 C(O)—, R 7 R 8 NC(O)—, R 7 OC(O)—, R 7 C(O)O—, R 7 C(O)NR 8 —, —CN or —NO 2 ; or Y is Y-1, Y-2, Y-3, Y-4, Y-5, Y-6, Y-7, Y-8, Y-9, Y-10, Y-11, Y-12 or Y-13, wherein # signifies the point of attachment;
wherein each R 9 , R 10 are independently hydrogen, alkyl, haloalkyl, alkyl substituted by thiol, alkylthioalkyl, hydroxyalkyl, alkoxylakyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, aryl, heteroaryl, heterocyclyl, R 7 S(O)—, R 7 S(O) 2 —, R 7 C(O)—, R 7 R 8 NC(O)—, R 7 OC(O)—, R 7 C(O)O—, R 7 C(O)NR 8 —;
each R 11 is independently hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, amino, alkylamino, haloalkylamino, dialkylamino, dihaloalkylamino, hydroxyalkyl, alkoxyalkyl, alkyl substituted by thiol or alkylthioalkyl;
each R 12 and R 13 is independently hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, amino, alkylamino, haloalkylamino, dialkylamino, dihaloalkylamino, hydroxyalkyl, alkoxyalkyl alkyl substituted by thiol or alkylthioalkyl; or
R 12 and R 13 together with the carbon atom to which they are bonded together form C═W;
W, W 1 and Z are independently O, S or NR 7 ;
L is a direct bond, —CR 3 R 4 —, —NR 8 — or —O—;
n is 1, 2, 3 or 4; and
m is 0, 1 or 2.
9. The isoxazoline compound of claim 1 , wherein the compound has the structure of formula
wherein:
R 1 is alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl;
A 1 and A 3 are independently hydrogen, halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl or haloalkynyl;
B 1 and B 2 are independently N or C—X;
each X is independently hydrogen, halogen, alkyl or haloalkyl; or two adjacent X together form a 5- or 6-membered ring together with the carbon atoms to which they are bonded by forming —CH 2 CH 2 CH 2 —, —CH═CH—CH═CH—, —CH 2 CH 2 O—, —CH 2 OCH 2 —, —OCH 2 O—, —CH 2 CH 2 S—, —CH 2 SCH 2 —, —SCH 2 S—, —CH 2 CH 2 CH 2 CH 2 —, —CH 2 CH 2 CH 2 O—, —CH 2 CH 2 OCH 2 —, —CH 2 OCH 2 O—, —OCH 2 CH 2 O—, —OCH 2 CH 2 S—, —SCH 2 CH 2 S—, —OCH═N— or —SCH═N—;
R 2 is hydrogen, halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl or haloalkynyl;
R 3 , R 4 , R 5 , R 6 , R 5′ and R 6′ are each independently hydrogen, halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl or haloalkynyl;
R 5 and R 6 together with the carbon atom to which they are bonded together form C═W; and/or
R 5′ and R 6′ together with the carbon atom to which they are bonded together form C═W, with the proviso that at least one of R 5 and R 6 or R 5′ and R 6′ , together with the carbon atom to which they are attached form the group C═W;
R 7 and R 8 are independently hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, aryl, heteroaryl, heterocyclyl, alkyl substituted by thiol, haloalkyl substituted by thiol, alkylthioalkyl, hydroxyalkyl or alkoxyalkyl;
Y is hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, alkylcycloalkyl, cycloalkylalkyl, aryl, heterocyclyl or heteroaryl each of which is unsubstituted or substituted with one or more of halogen, hydroxy, amino, alkyl- or di(alkyl)amino, alkyl, cycloalkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, R 7 S(O)—, R 7 S(O) 2 —, R 7 C(O)—, R 7 R 8 NC(O)—, R 7 OC(O)—, R 7 C(O)O—, R 7 C(O)NR 8 —, —CN or —NO 2 ; or Y is Y-1, Y-2, Y-3, Y-4, Y-5, Y-6, Y-7, Y-8, Y-9, Y-10, Y-11, Y-12 or Y-13, wherein # signifies the point of attachment;
wherein each R 9 , R 10 are independently hydrogen, alkyl, haloalkyl, alkyl substituted by thiol, alkylthioalkyl, hydroxyalkyl, alkoxylakyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, aryl, heteroaryl, heterocyclyl, R 7 S(O)—, R 7 S(O) 2 —, R 7 C(O)—, R 7 R 8 NC(O)—, R 7 OC(O)—, R 7 C(O)O—, R 7 C(O)NR 8 —;
each R 11 is independently hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, amino, alkylamino, haloalkylamino, dialkylamino, dihaloalkylamino, hydroxyalkyl, alkoxyalkyl, alkyl substituted by thiol or alkylthioalkyl;
each R 12 and R 13 is independently hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, amino, alkylamino, haloalkylamino, dialkylamino, dihaloalkylamino, hydroxyalkyl, alkoxyalkyl alkyl substituted by thiol or alkylthioalkyl; or
R 12 and R 13 together with the carbon atom to which they are bonded together form C═W;
W, W 1 and Z are independently O, S or NR 7 ;
L is a direct bond, —CR 3 R 4 —, —NR 8 — or —O—;
n is 1, 2, 3 or 4; and
m is 0, 1 or 2.
10. An isoxazoline compound of formula (ID):
wherein:
A 1 and A 3 are independently halogen or C 1 -C 4 haloalkyl;
B 1 and B 2 are independently N or C—X;
each X is independently hydrogen, halogen, alkyl or haloalkyl; or two adjacent X together form a 5- or 6-membered ring together with the carbon atoms to which they are bonded by forming —CH 2 CH 2 CH 2 —, —CH═CH—CH═CH—, —CH 2 CH 2 O—, —CH 2 OCH 2 —, —OCH 2 O—, —CH 2 CH 2 S—, —CH 2 SCH 2 —, —SCH 2 S—, —CH 2 CH 2 CH 2 CH 2 —, —CH 2 CH 2 CH 2 O—, —CH 2 CH 2 OCH 2 —, —CH 2 OCH 2 O—, —OCH 2 CH 2 O—, —OCH 2 CH 2 S—, —SCH 2 CH 2 S—, —OCH═N— or —SCH═N—;
R 2 is C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;
R 3 and R 4 are independently hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or halogen; or R 3 and R 4 together with the carbon atom to which they are bonded for the group C═O;
Y is hydrogen, C 1 -C 4 alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, alkylcycloalkyl, cycloalkylalkyl, aryl, heterocyclyl or heteroaryl each of which is unsubstituted or substituted with one or more of halogen, hydroxy, amino, alkyl- or di(alkyl)amino, alkyl, cycloalkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, R 7 S(O)—, R 7 S(O) 2 —, R 7 C(O)—, R 7 R 8 NC(O)—, R 7 OC(O)—, R 7 C(O)O—, R 7 C(O)NR 8 —, —CN or —NO 2 ; or Y is Y-1, Y-2, Y-3, Y-4, Y-5, Y-6, Y-7, Y-8, Y-9, Y-10, Y-11, Y-12 or Y-13, wherein # signifies the point of attachment;
wherein R 7 and R 8 are independently hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, aryl, heteroaryl, heterocyclyl alkyl substituted by thiol, haloalkyl substituted by thiol, alkylthioalkyl, hydroxyalkyl or alkoxyalkyl;
R 9 and R 10 are independently hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, thio-C 1 -C 4 -alkyl or C 1 -C 4 alkylthio-C 1 -C 4 -alkyl;
each R 11 is independently hydrogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, amino, alkylamino, haloalkylamino, dialkylamino, dihaloalkylamino, hydroxyalkyl, alkoxyalkyl alkyl substituted by thiol or alkylthioalkyl;
each R 12 and R 13 is independently hydrogen or C 1 -C 4 alkyl;
W and W 1 are O;
L is a direct bond, —CR 3 R 4 —, —NR 8 — or —O—;
n is 1, 2, 3 or 4; and
m is 0, 1 or 2.
11. An isoxazoline compound of formula (IE):
wherein:
A 1 and A 3 are independently halogen or C 1 -C 4 haloalkyl;
B 1 and B 2 are independently N or C—X;
each X is independently hydrogen, halogen, alkyl or haloalkyl; or two adjacent X together form a 5- or 6-membered ring together with the carbon atoms to which they are bonded by forming —CH 2 CH 2 CH 2 —, —CH═CH—CH═CH—, —CH 2 CH 2 O—, —CH 2 OCH 2 —, —OCH 2 O—, —CH 2 CH 2 S—, —CH 2 SCH 2 —, —SCH 2 S—, —CH 2 CH 2 CH 2 CH 2 —, —CH 2 CH 2 CH 2 O—, —CH 2 CH 2 OCH 2 —, —CH 2 OCH 2 O—, —OCH 2 CH 2 O—, —OCH 2 CH 2 S—, —SCH 2 CH 2 S—, —OCH═N— or —SCH═N—;
R 2 is hydrogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;
R 3 and R 4 are independently hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or halogen; or R 3 and R 4 together with the carbon atom to which they are bonded for the group C═O;
Y is hydrogen, C 1 -C 4 alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, alkylcycloalkyl, cycloalkylalkyl, aryl, heterocyclyl or heteroaryl each of which is unsubstituted or substituted with one or more of halogen, hydroxy, amino, alkyl- or di(alkyl)amino, alkyl, cycloalkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, R 7 S(O)—, R 7 S(O) 2 —, R 7 C(O)—, R 7 R 8 NC(O)—, R 7 OC(O)—, R 7 C(O)O—, R 7 C(O)NR 8 —, —CN or —NO 2 ; or Y is Y-1, Y-2, Y-3, Y-4, Y-5, Y-6, Y-7, Y-8, Y-9, Y-10, Y-11, Y-12 or Y-13, wherein # signifies the point of attachment;
wherein R 7 and R 8 are independently hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, aryl, heteroaryl, heterocyclyl alkyl substituted by thiol, haloalkyl substituted by thiol, alkylthioalkyl, hydroxyalkyl or alkoxyalkyl;
R 9 and R 10 are independently hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, thio-C 1 -C 4 -alkyl or C 1 -C 4 alkylthio-C 1 -C 4 -alkyl;
each R 11 is independently hydrogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, amino, alkylamino, haloalkylamino, dialkylamino, dihaloalkylamino, hydroxyalkyl, alkoxyalkyl alkyl substituted by thiol or alkylthioalkyl;
each R 12 and R 13 is independently hydrogen or C 1 -C 4 alkyl;
W and W 1 are O;
L is a direct bond, —CR 3 R 4 —, —NR 8 — or —O—;
n is 1, 2, 3 or 4; and
m is 0, 1 or 2.
12. The isoxazoline compound of claim 11 , wherein B 1 and B 2 are C—H.
13. The isoxazoline compound of claim 11 , wherein B 1 and B 2 are C—X where
each X together form —CH═CH—CH═CH— thereby forming a naphthalene ring together with the carbon atoms to which they are attached.
14. A composition for the treatment or prevention of a parasitic infection or infestation in an animal comprising an effective amount of an isoxazoline compound of formula (I) of claim 1 in combination with a pharmaceutically acceptable carrier.
15. A composition for the protection of crops, plants, plant propagation material or material made from wood from pests comprising a pesticidally effective amount of an isoxazoline compound of formula (I) of claim 1 in combination with an agriculturally acceptable carrier or diluent.
16. A method for the treatment or prevention of a parasitic infection or infestation in an animal, comprising administering to the animal a parasiticidally effective amount of an isoxazoline compound of formula (I) of claim 1 to the animal.
17. A method for protecting crops and growing plants from attack or infestation by insect pests, comprising contacting a plant, or soil or water in which the plant is growing, with an isoxazoline compound of formula (I) of claim 1 .
18. An isoxazoline compound wherein the compound has the structure
19. A composition for the treatment or prevention of a parasitic infection or infestation in an animal comprising an effective amount of an isoxazoline compound of formula (IB) of claim 8 in combination with a pharmaceutically acceptable carrier.
20. A composition for the treatment or prevention of a parasitic infection or infestation in an animal comprising an effective amount of an isoxazoline compound of formula (ID) of claim 10 in combination with a pharmaceutically acceptable carrier.
21. A composition for the treatment or prevention of a parasitic infection or infestation in an animal comprising an effective amount of an isoxazoline compound of formula (IE) of claim 11 in combination with a pharmaceutically acceptable carrier.
22. A composition for the protection of crops, plants, plant propagation material or material made from wood from pests comprising a pesticidally effective amount of an isoxazoline compound of formula (IB) of claim 8 in combination with an agriculturally acceptable carrier or diluent.
23. A composition for the protection of crops, plants, plant propagation material or material made from wood from pests comprising a pesticidally effective amount of an isoxazoline compound of formula (ID) of claim 10 in combination with an agriculturally acceptable carrier or diluent.
24. A composition for the protection of crops, plants, plant propagation material or material made from wood from pests comprising a pesticidally effective amount of an isoxazoline compound of formula (IE) of claim 11 in combination with an agriculturally acceptable carrier or diluent.
25. A method for the treatment or prevention of a parasitic infection or infestation in an animal, comprising administering to the animal a parasiticidally effective amount of an isoxazoline compound of formula (IB) of claim 8 to the animal.
26. A method for the treatment or prevention of a parasitic infection or infestation in an animal, comprising administering to the animal a parasiticidally effective amount of an isoxazoline compound of formula (ID) of claim 10 to the animal.
27. A method for the treatment or prevention of a parasitic infection or infestation in an animal, comprising administering to the animal a parasiticidally effective amount of an isoxazoline compound of formula (IE) of claim 11 to the animal.
28. A method for protecting crops and growing plants from attack or infestation by insect pests, comprising contacting a plant, or soil or water in which the plant is growing, with an isoxazoline compound of formula (IB) of claim 8 .
29. A method for protecting crops and growing plants from attack or infestation by insect pests, comprising contacting a plant, or soil or water in which the plant is growing, with an isoxazoline compound of formula (ID) of claim 10 .
30. A method for protecting crops and growing plants from attack or infestation by insect pests, comprising contacting a plant, or soil or water in which the plant is growing, with an isoxazoline compound of formula (IE) of claim 11 .