Isoxazoline-substituted benzamide compound and pesticide

Patent metadata

Field	Value
Publication number	US-10596157-B2
Application number	US-201815972939-A
Country	US
Kind code	B2
Filing date	May 7, 2018
Priority date	Mar 5, 2004
Publication date	Mar 24, 2020
Grant date	Mar 24, 2020

Abstract

A substituted alkenylbenzene compound of formula (4):

wherein X 1 is selected from the group consisting of a halogen atom, —SF 5 , C 1 -C 6 haloalkyl, hydroxy C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy C 1 -C 6 haloalkyl, C 3 -C 8 halocycloalkyl, C 1 -C 6 haloalkoxy, C 1 -C 3 haloalkoxy C 1 -C 3 haloalkoxy, C 1 -C 6 haloalkylthio, C 1 -C 6 haloalkylsulfinyl and C 1 -C 6 haloalkylsulfonyl; X 3 is selected from the group consisting of a hydrogen atom, halogen atom, cyano, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy and C 1 -C 6 alkylthio; X 4 is selected from the group consisting of a hydrogen atom, halogen atom, cyano, C 1 -C 4 alkoxy and C 1 -C 4 haloalkoxy; R 3 is —C(R 3a )(R 3b )R 3c , where R 3a and R 3b independently of each other are a halogen atom, or R 3a and R 3b together form 3- to 6-membered ring together with the carbon atom bonding them by forming a C 2 -C 5 haloalkylene chain, and R 3c is selected from the group consisting of a hydrogen atom, halogen atom, C 1 -C 5 haloalkyl, C 1 -C 4 haloalkoxy and C 1 -C 4 haloalkylthio, with a proviso that in case where X 1 is a fluorine atom, chlorine atom or trifluoromethyl, and both X 2 and X 3 are a hydrogen atom, in case where both X 1 and X 2 are fluorine atom and X 3 is a hydrogen atom, and in case where both X 1 and X 2 are trifluoromethyl and X 3 is a hydrogen atom, R 3c is a hydrogen atom, chlorine atom, bromine atom, iodine atom, C 1 -C 5 alkyl, C 1 -C 5 haloalkyl, C 1 -C 4 haloalkoxy or C 1 -C 4 haloalkylthio.

First claim

The invention claimed is:

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

Assignees

• Nissan Chemical Corp

Inventors

• Mita Takeshi
• Kikuchi Takamasa
• Mizukoshi Takashi
• Yaosaka Manabu
• Komoda Mitsuaki
• Takii Shinji

Classifications

• A61P33/12

  Schistosomicides · CPC title

• C07D413/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07C255/50

  to carbon atoms of non-condensed six-membered aromatic rings · CPC title

• C07C323/09

  having sulfur atoms of thio groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton · CPC title

• C07C211/52

  the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups · CPC title