Isoxazoline-substituted benzamide compound and pesticide

• US 8,673,951 B2
• Filed: 01/20/2011
• Issued: 03/18/2014
• Est. Priority Date: 09/02/2005
• Status: Active Grant

• Current Assignee: Nissan Chemical Industries Limited (Nissan Chemical Corporation)
• Original Assignee: Nissan Chemical Industries Limited (Nissan Chemical Corporation)
• Inventors: Mita, Takeshi, Furukawa, Yuki, Toyama, Ken-ichi, Yaosaka, Manabu, Ikeda, Eitatsu, Masuzawa, Yoshihide, Komoda, Mitsuaki
• Primary Examiner(s): Young, Shawquia
• Application Number:
  US13/010,479
• Publication Number:
  US 20110144334A1
• Time in Patent Office: 1,153 Days
• Field of Search: 548/240, 514/378
• US Class Current: 514/378
• CPC Class Codes: A01N 43/80 five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
• CPC Class Codes: A61P 33/00 Antiparasitic agents
• CPC Class Codes: A61P 33/02 Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
• CPC Class Codes: A61P 33/04 Amoebicides
• CPC Class Codes: A61P 33/10 Anthelmintics
• CPC Class Codes: A61P 33/14 Ectoparasiticides, e.g. scabicides
• CPC Class Codes: C07C 237/32 having the nitrogen atom of the carboxamide group bound to an acyclic carbon atom of a hydrocarbon radical substituted by oxygen atoms
• CPC Class Codes: C07C 237/36 having the nitrogen atom of the carboxamide group bound to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
• CPC Class Codes: C07D 213/75 Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
• CPC Class Codes: C07D 213/81 Amides; Imides
• CPC Class Codes: C07D 237/20 Nitrogen atoms nitro radicals C07D237/12
• CPC Class Codes: C07D 239/42 One nitrogen atom nitro radicals C07D239/30
• CPC Class Codes: C07D 241/20 Nitrogen atoms nitro radicals C07D241/16
• CPC Class Codes: C07D 401/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 413/04 directly linked by a ring-member-to-ring-member bond

Abstract

An isoxazoline-substituted benzamide compound of formula (1) or a salt thereof:

wherein A¹, A² and A³ independently of one another are carbon atom or nitrogen atom, G is benzene ring, etc., W is oxygen atom or sulfur atom, etc., X is halogen atom, C₁-C₆haloalkyl, etc., Y is halogen atom, C₁-C₆alkyl, etc., R¹ is —CH═NOR^1a, —C(O)OR^1c, —C(O)NHR^1d, phenyl substituted with (Z)_p1, D-14, D-52, D-53, D-55 to D-59, etc., R^1a is C₁-C₆alkyl, etc., R^1c is C₁-C₆alkyl, etc., R^1d is hydrogen atom, —C(O)R¹⁵, —C(O)OR¹⁵, etc., R² is C₁-C₆alkyl, —CH₂R^14a, C₁-C₆alkynyl, —C(O)R¹⁵, —C(O)OR¹⁵, etc., further when R¹ is —CH═NOR^1a, —C(O)OR^1c or —C(O)N(R^1e)R^1d, R² may be hydrogen atom, R³ is C₁-C₆haloalkyl, etc., R^14a is cyano, —OR²⁵, etc., R¹⁵ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄alkylthio C₁-C₄alkyl, C₃-C₆cycloalkyl, C₂-C₆alkenyl, etc., R²⁵ is C₁-C₄alkyl, C₁-C₄haloalkyl, —C(O)R³² or —C(O)OR³², etc., R³² is C₁-C₆alkyl or C₃-C₆cycloalkyl, etc., Z is halogen atom, cyano, nitro, C₁-C₆alkyl, C₁-C₆alkoxy, etc., m is an integer of 0 to 5, n is an integer of 0 to 4, p1 is an integer of 1 to 5. The pesticide containing these compounds.

Claims

1. An isoxazoline-substituted benzamide compound of formula (1) or a salt thereof:

2. The isoxazoline-substituted benzamide compound or the salt thereof according to claim 1, wherein

G is an aromatic 6-membered ring shown in G-1

3. The isoxazoline-substituted benzamide compound or the salt thereof according to claim 2, wherein

A¹, A² and A³ are carbon atoms,

G is G-1,

X is halogen atom, cyano, nitro, —

SF₅, C₁-C₆alkyl, C₁-C₆haloalkyl, hydroxyC₁-C₆haloalkyl, C₁-C₆alkoxyC₁-C₆haloalkyl, C₃-C₈halocycloalkyl, —

OR⁵, —

OSO₂R⁵ or —

S(O)_rR⁵, when m is 2 or 3, each X may be identical with or different from each other,

Y is halogen atom, cyano, nitro, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₄alkyl arbitrarily substituted with R⁴, —

OR⁵, —

SR⁵, —

NH₂, —

N(R⁷)R⁶ or —

C(S)NH₂, when n is 2, each Y may be identical with or different from each other,

R¹ is —

C(O)OR^1c, —

C(O)SR^1c, —

C(S)OR^1c, —

C(O)N(R^1e)R^1d, —

C(S)N(R^1e)R^1d, phenyl, phenyl substituted with (Z)_p1, D-3, D-8, D-10, D-11, D-13 to D-15, D-17, D-22, D-35, D-52 to D-58 or D-59,

R^1a is hydrogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl C₁-C₄alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl,

R^1b is hydrogen atom or C₁-C₆alkyl,

R^1c is C₁-C₆alkyl, C₁-C₄alkyl arbitrarily substituted with R¹⁴ or C₃-C₆cycloalkyl,

R^1d is hydrogen atom, —

C(O)R¹⁵, —

C(O)OR¹⁵ or —

C(O)SR¹⁵,

R² is C₁-C₆alkyl, —

CH₂R^14a, E-5, E-24, C₃-C₆alkynyl, —

C(O)R¹⁵, —

C(O)OR¹⁵, —

C(O)SR¹⁵, —

C(S)OR¹⁵, —

C(S)SR¹⁵, —

C(O)C(O)OR¹⁵, C₁-C₆haloalkylthio, —

SN(R²⁰)R¹⁹, phenyl or phenyl substituted with (Z)_p1,

further when R¹ is —

C(O)OR^1c, —

C(O)SR^1c, or —

C(S)OR^1c, R² may be hydrogen atom, when R¹ is phenyl, phenyl substituted with (Z)_p1, D-3, D-8, D-10, D-11, D-13 to D-15, D-17, D-22, D-35, D-52 to D-58 or D-59, R² may be C₁-C₆haloalkyl or C₃-C₆alkenyl, or R² together with R¹ may form ═

C(R^2b)R^2a,

R^2a is C₁-C₆alkoxy or di(C₁-C₆alkyl)amino,

R^2b is R^1b, C₁-C₆alkylthio, —

SCH₂R^14a, C₃-C₆alkenylthio, C₃-C₆alkynylthio or C₁-C₆alkylcarbonylthio,

R³ is C₁-C₆haloalkyl or C₃-C₈halocycloalkyl,

R⁴ is —

OH, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio or C₁-C₆haloalkylthio,

R⁵ is C₁-C₆alkyl, C₁-C₆haloalkyl or C₁-C₃haloalkoxy C₁-C₃haloalkyl,

R⁶ is C₁-C₆alkyl, —

CHO, C₁-C₆alkylcarbonyl, C₁-C₆haloalkylcarbonyl, C₁-C₆alkoxycarbonyl, C₁-C₆alkylthiocarbonyl, C₁-C₆alkoxythiocarbonyl, C₁-C₆alkyldithiocarbonyl, C₁-C₆alkylsulfonyl or C₁-C₆haloalkylsulfonyl,

R⁷ is hydrogen atom or C₁-C₆alkyl

R¹⁴ is cyano, C₃-C₆cycloalkyl, C₁-C₆alkoxy, C₁-C₄alkoxy C₁-C₄alkoxy, C₁-C₆alkylthio, —

S(D-52), —

S(D-55), C₁-C₆alkylsulfonyl, —

NHC(O)R³², —

NHC(O)OR³², C₁-C₆alkylcarbonyl or C₁-C₆alkoxycarbonyl,

R^14a is cyano, —

OR²⁵, —

NHC(O)OR³², —

S(O)_rR²⁷, C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl or phenyl,

R¹⁵ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₄alkyl arbitrarily substituted with R³¹, C₃-C₆cycloalkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, phenyl, phenyl substituted with (Z)_p1, D-52, D-53 or D-54,

R¹⁹ is C₁-C₆alkyl, C₁-C₆alkoxycarbonyl C₁-C₄alkyl or C₁-C₆alkoxycarbonyl,

R²⁰ is C₁-C₆alkyl or benzyl,

R²⁵ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₄alkoxy C₁-C₄alkyl, benzyl, C₃-C₆alkenyl, C₃-C₆alkynyl, —

C(O)R³² or —

C(O)OR³²,

R²⁷ is C₁-C₆alkyl, C₁-C₆haloalkyl, —

C(O)R³² or —

C(S)OR³²,

R³¹ is C₃-C₆cycloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl or phenyl,

R³² is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl or phenyl,

p1 is an integer of 1 to 3,

p2 and p3 are an integer of 0 to 2, and

p4 is an integer of 0 or 1.

4. The isoxazoline-substituted benzamide compound or the salt thereof according to claim 3, wherein

W is oxygen atom,

X is halogen atom, cyano, nitro, C₁-C₆alkyl, C₁-C₆haloalkyl, —

OR⁵ or —

S(O)_rR⁵, when m is 2 or 3, each X may be identical with or different from each other,

Y is halogen atom, cyano, nitro, C₁-C₆alkyl, C₁-C₆haloalkyl, —

OR⁵, —

SR⁵, —

NH₂ or —

N(R⁷)R⁶,

R¹ is —

C(O)OR^1c, —

C(O)N(R^1e)R^1d, phenyl substituted with (Z)_p1, D-52, D-55, D-56, D-57 or D-58,

R^1a is C₁-C₆alkyl,

R^1c is C₁-C₆alkyl or C₃-C₆cycloalkyl,

R^1d is hydrogen atom, —

C(O)R¹⁵ or —

C(O)OR¹⁵,

R² is C₁-C₆alkyl, —

CH₂R^14a, E-5, C₃-C₆alkynyl, —

C(O)R¹⁵, —

C(O)OR¹⁵, —

C(O)C(O)OR¹⁵ or C₁-C₆haloalkylthio, further when R¹ is —

C(O)OR^1c, R² may be hydrogen atom,

R³ is C₁-C₆haloalkyl,

Z is halogen atom, cyano, nitro, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl or C₁-C₆alkylsulfonyl, when p1, p2 or p3 is an integer of 2 or more, each Z may be identical with or different from each other,

R⁵ is C₁-C₆alkyl or C₁-C₆haloalkyl,

R⁶ is C₁-C₆alkyl, —

CHO, C₁-C₆alkylcarbonyl or C₁-C₆alkoxycarbonyl,

R^14a is cyano, —

OR²⁵ or —

NHC(O)OR³²,

R¹⁵ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄alkylthio C₁-C₄alkyl, C₁-C₄alkylsulfinyl C₁-C₄alkyl, C₁-C₄alkylsulfonyl C₁-C₄alkyl, C₃-C₆cycloalkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, phenyl, phenyl substituted with (Z)_p1 or D-52,

R²⁵ is C₁-C₄alkyl, C₁-C₄haloalkyl, —

C(O)R³² or —

C(O)OR³²,

R³² is C₁-C₆alkyl or C₃-C₆cycloalkyl,

n is an integer of 0 or 1,

q3 is 0, and

t is 0.

5. The isoxazoline-substituted benzamide compound or the salt thereof according to claim 4, wherein

R¹ is —

C(O)OR^1c,

R^1c is C₁-C₆alkyl or C₃-C₆cycloalkyl,

R² is hydrogen atom, C₁-C₆alkyl, —

CH₂R^14a, E-5, —

C(O)R¹⁵, C₁-C₆alkoxycarbonyl, C₁-C₆haloalkoxycarbonyl or C₁-C₆haloalkylthio,

R^14a is cyano, —

OR²⁵ or —

NHC(O)OR³²,

R¹⁵ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄alkylthio C₁-C₄alkyl or C₃-C₆cycloalkyl,

R²⁵ is C₁-C₄alkyl, C₁-C₄haloalkyl or —

C(O)OR³², and

R³² is C₁-C₆alkyl.

6. The isoxazoline-substituted benzamide compound or the salt thereof according to claim 4, wherein

R¹ is —

C(O)N(R^1e)R^1d,

R^1d is hydrogen atom, —

C(O)R¹⁵ or —

C(O)OR¹⁵,

R² is C₁-C₆alkyl, and

R¹⁵ is C₁-C₆alkyl or C₁-C₆haloalkyl.

7. The isoxazoline-substituted benzamide compound or the salt thereof according to claim 4, wherein

R¹ is phenyl substituted with (Z)_p1, D-52, D-55, D-56, D-57 or D-58,

R² is C₁-C₆alkyl, —

CH₂R^14a, C₃-C₆alkynyl, —

C(O)R¹⁵, —

C(O)OR¹⁵ or —

C(O)C(O)OR¹⁵,

Z is halogen atom, cyano, nitro, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl or C₁-C₆alkylsulfonyl, when p1, p2 or p3 is an integer of 2 or more, each Z may be identical with or different from each other,

R^14a is cyano or —

OR²⁵,

R¹⁵ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄alkylthio C₁-C₄alkyl, C₁-C₄alkylsulfinyl C₁-C₄alkyl, C₁-C₄alkylsulfonyl C₁-C₄alkyl, C₃-C₆cycloalkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, phenyl, phenyl substituted with (Z)_p1 or D-52,

R²⁵ is C₁-C₄alkyl, C₁-C₄haloalkyl, —

C(O)R³² or —

C(O)OR³², and

R³² is C₁-C₆alkyl or C₃-C₆cycloalkyl.

8. A pesticide containing as an active ingredient one or more selected from isoxazoline-substituted benzamide compound and the salt thereof according to claim 1.

9. An agrochemical containing as an active ingredient one or more selected from isoxazoline-substituted benzamide compound and the salt thereof according to claim 1.

10. An endo- or ecto-parasiticide for mammals or birds containing as an active ingredient one or more selected from isoxazoline-substituted benzamide compound and the salt thereof according to claim 1.

11. An insecticide or acaricide containing as an active ingredient one or more selected from isoxazoline-substituted benzamide compound and the salt thereof according to claim 1.