Granted Patent B2

US 10,596,157 · App. 15/972,939 · Granted Mar 24, 2020

Inventors: Takeshi Mita (Funabashi, JP); Takamasa Kikuchi (Funabashi, JP); Takashi Mizukoshi (Funabashi, JP); Manabu Yaosaka (Funabashi, JP); Mitsuaki Komoda (Tokyo, JP); Shinji Takii (Shiraoka, JP)

Assignee: Nissan Chemical Corporation

A61K31/421A01N43/80A61K9/0053C07C25/02C07C25/06C07C25/08C07C25/13C07C25/24C07C43/1742C07C43/1745C07C205/11C07C205/12C07C211/52C07C251/48C07C255/29C07C255/50C07C255/60C07C281/02C07C323/09C07D261/04C07D261/16C07D413/04C07D413/06C07D413/12C07D413/14C07D417/06C07D417/12C07F7/0812

Abstract

Claims (129)

1. A method for protecting a mammal from a flea comprising orally administering to the mammal a pesticidally effective amount sufficient to protect the mammal from the flea of a compound of Formula (1) or a salt thereof,

wherein

A 1 , A 2 and A 3 independently of one another are carbon atom;

G is benzene ring;

W is oxygen atom or sulfur atom;

X is halogen atom, C 1 -C 6 alkyl, C 1 -C 6 alkyl arbitrarily substituted with R 4 , —OR 5 or —S(O) r R 5 ;

Y is halogen atom, C 1 -C 6 alkyl, or —S(O) r R 5 ;

R 1 is C 1 -C 6 alkyl arbitrarily substituted with R 16 , C 3 -C 6 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, —N(R 20 )R 19 , —C(O)N(R 10 )R 9 , —C(S)N(R 10 )R 9 , phenyl substituted with (Z) p1 , D-15, D-47, D-50, D-51, E-4, E-5, E-6, E-9 or E-23, wherein

D-15, D-47, D-50, and D-51 are aromatic heterocyclic rings of the following formulae, respectively

 and

E-4, E-5, E-6, E-9 and E-23 are saturated heterocyclic rings of the following formulae, respectively

R 2 is hydrogen atom, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 4 alkoxy C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 alkynyl, —C(O)R 9 or —C(O)OR 9 ;

R 3 is C 1 -C 6 haloalkyl;

R 4 is halogen atom;

R 5 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl;

R 9 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy C 1 -C 4 alkyl, C 3 -C 6 alkenyl;

R 10 is hydrogen atom;

R 15 is C 1 -C 6 alkyl;

R 16 is halogen atom, cyano, C 3 -C 6 cycloalkyl, —OR 25 , —S(O) r R 27 , —C(O)R 28 , —C(O)OR 28 , —C(O)NHR 29 , —C(O)N(R 29 )R 28 , —C(R 31 )═NOR 30 , phenyl, D-1, D-3, D-10, D-17, D-21, D-22, D-23, D-31, D-34, D-35, D-38, D-47, D-48, D-49, D-50, D-51, D-53, E-4 or E-10, wherein

D-1, D-3, D-10, D-17, D-21, D-22, D-23, D-31, D-34, D-35, D-38, D-47, D-48, D-49, D-50, D-51, and D-53 are aromatic heterocyclic rings of the following formulae, respectively

 and

E-4 and E-10 are saturated heterocyclic rings of the following formulae, respectively

R 19 is —C(O)OR 28 , phenyl, D-47 or D-50, wherein

D-47 and D-50 are aromatic heterocyclic rings of the following formulae, respectively

R 20 is hydrogen atom, C 1 -C 6 alkyl;

R 22 is C 1 -C 6 alkoxy or two R 22 s present on the same carbon atom may together form oxo;

R 23 is C 1 -C 6 alkyl substituted with R 32 ;

R 25 is hydrogen atom, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;

R 27 is C 1 -C 6 alkyl;

R 28 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 alkenyl or C 3 -C 6 alkynyl;

R 29 is hydrogen atom or C 1 -C 6 alkyl;

R 30 is C 1 -C 6 alkyl;

R 31 is C 1 -C 6 alkyl;

R 32 is halogen atom;

Z is halogen atom, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;

m is an integer of 0 to 5;

n is an integer of 0 to 4;

p1 is an integer of 1 to 5;

p2 is an integer of 0 to 4;

p3 is an integer of 0 to 3;

p4 is an integer of 0 to 2;

p5 is an integer of 0 or 1;

q2 is an integer of 0 to 5;

q3 is an integer of 0 to 7;

q4 is an integer of 0 to 9;

r is an integer of 0 to 2; and

t is an integer of 0 or 1.

2. A method according to claim 1 , wherein the mammal is livestock.

3. A method according to claim 1 , wherein the mammal is a canine.

4. A method according to claim 1 , wherein the mammal is a feline.

5. A method according to claim 1 , wherein the mammal is a dog.

6. A method according to claim 1 , wherein the mammal is a cat.

7. A method for protecting a mammal from a flea comprising orally administering to the mammal a pesticidally effective amount sufficient to protect the mammal from the flea of a compound of Formula (1) or a salt thereof,

wherein

A 1 , A 2 and A 3 independently of one another are carbon atom;

G is benzene ring;

W is oxygen atom or sulfur atom;

X is halogen atom, C 1 -C 6 alkyl arbitrarily substituted with R 4 , —OR 5 or —S(O) r R 5 ;

Y is halogen atom, C 1 -C 6 alkyl, or —S(O) r R 5 ;

R 1 is C 1 -C 6 alkyl arbitrarily substituted with R 16 , C 3 -C 6 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, or —N(R 20 )R 19 ,

R 2 is hydrogen atom, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 alkynyl, —C(O)R 9 or —C(O)OR 9 ;

R 3 is C 1 -C 6 haloalkyl;

R 4 is halogen atom;

R 5 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl;

R 9 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy C 1 -C 4 alkyl, C 3 -C 6 alkenyl;

R 15 is C 1 -C 6 alkyl;

R 16 is halogen atom, cyano, C 3 -C 6 cycloalkyl, —OR 25 , —S(O) r R 27 , —C(O)R 28 , —C(O)OR 28 , —C(O)NHR 29 , —C(O)N(R 29 )R 28 , —C(R 31 )═NOR 30 , phenyl, D-1, D-3, D-10, D-17, D-21, D-22, D-23, D-31, D-34, D-35, D-47, D-48, D-49, D-50, D-51, D-53, E-4 or E-10, wherein

D-1, D-3, D-10, D-17, D-21, D-22, D-23, D-31, D-34, D-35, D-47, D-48, D-49, D-50, D-51 and D-53 are aromatic heterocyclic rings of the following formulae, respectively

 and

E-4 and E-10 are saturated heterocyclic rings of the following formulae, respectively

R 19 is —C(O)OR 28 , phenyl, D-47 or D-50, wherein

D-47 and D-50 are aromatic heterocyclic rings of the following formulae, respectively

R 20 is hydrogen atom, C 1 -C 6 alkyl;

R 25 is C 1 -C 6 alkyl;

R 27 is C 1 -C 6 alkyl;

R 28 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 alkenyl or C 3 -C 6 alkynyl;

R 29 is hydrogen atom or C 1 -C 6 alkyl;

R 30 is C 1 -C 6 alkyl;

R 31 is C 1 -C 6 alkyl;

Z is halogen atom, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;

m is an integer of 0 to 5;

n is an integer of 0 to 4;

p2 is an integer of 0 to 4;

p3 is an integer of 0 to 3;

p4 is an integer of 0 to 2;

p5 is an integer of 0 or 1;

q2 is an integer of 0;

q3 is an integer of 0;

r is an integer of 0 to 2; and

t is an integer of 0 or 1.

8. A method according to claim 7 , wherein the mammal is livestock.

9. A method according to claim 7 , wherein the mammal is a canine.

10. A method according to claim 7 , wherein the mammal is a feline.

11. A method according to claim 7 , wherein the mammal is a dog.

12. A method according to claim 7 , wherein the mammal is a cat.

13. A method for protecting a mammal from a flea comprising orally administering to the mammal a pesticidally effective amount sufficient to protect the mammal from the flea of a compound of Formula (1) or a salt thereof,

wherein

A 1 , A 2 and A 3 independently of one another are carbon atom;

G is benzene ring;

W is oxygen atom;

X is halogen atom, C 1 -C 6 alkyl arbitrarily substituted with R 4 or —OR 5 ;

Y is halogen atom or C 1 -C 6 alkyl;

R 1 is C 1 -C 6 alkyl arbitrarily substituted with R 16 ;

R 2 is hydrogen atom, C 1 -C 6 alkyl, —C(O)R 9 or —C(O)OR 9 ;

R 3 is C 1 -C 6 haloalkyl;

R 4 is halogen atom;

R 5 is C 1 -C 6 haloalkyl;

R 9 is C 1 -C 6 alkyl;

R 16 is —OR 25 , —S(O) r R 27 , —C(O)NHR 29 , —C(O)N(R 29 )R 28 , D-21, D-22, D-23, D-47, D-48 or E-4; wherein

D-21, D-22, D-23, and D-47 are aromatic heterocyclic rings of the following formulae, respectively

 and

E-4 is a saturated heterocyclic ring of the following formulae

R 25 is C 1 -C 6 alkyl;

R 27 is C 1 -C 6 alkyl;

R 28 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 alkenyl or C 3 -C 6 alkynyl; and

R 29 is hydrogen atom or C 1 -C 6 alkyl;

Z is halogen atom or C 1 -C 6 haloalkyl;

m is an integer of 0 to 5;

n is an integer of 0 to 4;

p2 is an integer of 0 to 4;

p4 is an integer of 0 to 2;

q3 is an integer of 0;

r is an integer of 0 to 2; and

t is an integer of 0 or 1.

14. A method according to claim 13 , wherein the mammal is livestock.

15. A method according to claim 13 , wherein the mammal is a canine.

16. A method according to claim 13 , wherein the mammal is a feline.

17. A method according to claim 13 , wherein the mammal is a dog.

18. A method according to claim 13 , wherein the mammal is a cat.

Assignments (1)

Priority Claims (2)

Continuity (9)