Parasite- and hygienic pest-controlling agent

Patent metadata

Field	Value
Publication number	US-2017190695-A1
Application number	US-201715466260-A
Country	US
Kind code	A1
Filing date	Mar 22, 2017
Priority date	Nov 19, 2010
Publication date	Jul 6, 2017
Grant date	—

Abstract

There is provided a novel agent for controlling harmful arthropods or nematodes that are parasites and hygienic pests for animals. An ecto- or endo-parasiticide for mammals or the like comprising as active ingredient, one or more selected from substituted benzamide compounds of formula (1) or salts thereof:

wherein A 1 is C—X 3 or nitrogen atom, etc., A 2 and A 3 are C—H, etc., A 4 is C—H or nitrogen atom, etc., G is G-2a, etc., W is oxygen atom or sulfur atom, X 1 is halogen atom, trifluoromethyl, etc., X 2 is hydrogen atom, halogen atom, trifluoromethyl, etc., X 3 is hydrogen atom, halogen atom, etc., Y 1 is hydrogen atom, halogen atom, methyl, etc., R 1 is trifluoromethyl, etc., R 2 is E-3a, etc., R 3 is hydrogen atom, etc., p is an integer of 0 to 2.

First claim

1 . A method for controlling parasites and hygienic pests comprising:
administering to an animal a compound comprising a parasite- and hygienic pest-controlling composition comprising as an active ingredient a substituted benzamide compound of formula (1) or a salt thereof:

wherein A 3 is C—X 3 or nitrogen atom,
A 2 , A 3 and A 4 are independently of one another C—Y 2 or nitrogen atom,
G is a heterocyclic ring of following structural formulae G-1 to G-7:

W is oxygen atom or sulfur atom,
X 1 is hydrogen atom, halogen atom, C 1 -C 3 haloalkyl, halocyclopropyl, —OR 4 , —SF 5 or C 1 -C 3 haloalkylthio,
X 2 is hydrogen atom, halogen atom, cyano, nitro, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, —OR 4 , —S(O) p R 4 or —NH 2 ,
X 3 is hydrogen atom, halogen atom, cyano, methyl, methoxy, difluoromethoxy, methylthio, —NH 2 or dimethylamino, or X 3 together with X 1 optionally forms 5-membered or 6-membered ring together with carbon atoms to which each of X 1 and X 3 is bonded by forming —CF 2 OCF 2 —, —OCF 2 O—, —CF 2 OCF 2 O— or —OCF 2 CF 2 O—,
Y 1 is hydrogen atom, halogen atom, cyano, nitro, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, (C 1 -C 2 )alkyl substituted with R 5 , C 3 -C 4 cycloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, —N(R 7 )R 6 , —C(S)NH 2 , C 2 -C 3 alkynyl, trimethylsilylethynyl, phenyl, phenyl substituted with (Z) n1 or D,
D is an aromatic heterocyclic ring of following structural formulae D-1 to D-3, D-7, D-11 and D-19 to D-23:

Z is halogen atom, cyano, nitro, methyl, trifluoromethyl, methoxy, methylthio, methylsulfinyl, methylsulfonyl, —NH 2 or dimethylamino, when n1 to n4 are an integer of 2 or more, each Z may be identical with or different from each other,
Y 2 is hydrogen atom, halogen atom or methyl, or when two Y 2 s are adjacent, the adjacent two Y 2 s may form 5-membered or 6-membered ring together with carbon atoms to which the two Y 2 s are bonded by forming ═NSN═ or —CH═CHCH═CH—, in this case, hydrogen atoms bonded to each carbon atom forming the ring may be arbitrarily substituted with Z, further when it is substituted with two or more Zs, each Z may be identical with or different from each other,
R 1 is C 1 -C 3 haloalkyl or halocyclopropyl,
R 1a is hydrogen atom, halogen atom, C 1 -C 3 alkyl, C 1 -C 3 alkylthiomethyl, C 1 -C 3 haloalkylthiomethyl, C 1 -C 3 alkylsulfinylmethyl, C 1 -C 3 haloalkylsulfinylmethyl, C 1 -C 3 alkylsulfonylmethyl, C 1 -C 3 haloalkylsulfonylmethyl, —OH, C 1 -C 3 alkylthio or C 1 -C 3 alkylsulfonyl,
R 1b is hydrogen atom or halogen atom, or R 1b together with R 1a optionally forms C 1 -C 4 alkylidene, phenylmethylidene, hydroxyimino or C 1 -C 3 alkoxyimino,
R 1c is C 1 -C 3 alkyl,
R 2 is E or (C 1 -C 3 )alkyl substituted with E,
E is a heterocyclic ring of following structural formulae selected from the group consisting of E-1, E-2, E-3, E-4, E-5, E-7, E-8, E-9, E-10, E-11, E-12, and E-13:

R 3 is hydrogen atom, C 1 -C 4 alkyl, (C 1 -C 2 )alkyl substituted with R 11 , C 3 -C 4 cycloalkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, —C(O)R 12 , —C(O)OR 13 , —C(O)C(O)OR 13 or C 1 -C 3 haloalkylthio, R 4 is C 1 -C 3 alkyl, C 1 -C 3 haloalkyl or C 1 -C 2 haloalkoxy (C 1 -C 2 )haloalkyl, R 5 is —OH, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio or C 1 -C 3 haloalkylthio,
R 6 is hydrogen atom, C 1 -C 4 alkyl, —CHO, C 1 -C 3 alkylcarbonyl, C 1 -C 3 haloalkylcarbonyl, C 3 -C 4 cycloalkylcarbonyl, C 1 -C 3 alkoxycarbonyl, C 1 -C 3 alkylthiocarbonyl, C 1 -C 3 alkoxythiocarbonyl, C 1 -C 3 alkyldithiocarbonyl, C 1 -C 3 alkylsulfonyl or C 1 -C 3 haloalkylsulfonyl,
R 7 is hydrogen atom or C 1 -C 3 alkyl,
R 8 is C 1 -C 3 alkyl,
R 9 is hydrogen atom, cyano or C 1 -C 2 haloalkylcarbonyl,
R 10 is hydrogen atom, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, hydroxy (C 1 -C 2 )alkyl, C 1 -C 3 alkoxy (C 1 -C 2 )alkyl, benzyl, C 3 -C 4 cycloalkyl, oxetan-3-yl, thietan-3-yl, C 3 -C 4 alkynyl, C 3 -C 4 alkenyl, phenyl or phenyl substituted with (Z) n1 ,
R 11 is cyano, C 3 -C 4 cycloalkyl, —OR 14 , 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, C 1 -C 3 alkoxycarbonyl, —C(O)NH 2 , —C(S)NH 2i phenyl or D-23,
R 12 is hydrogen atom, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 3 alkoxy (C 1 -C 2 )alkyl, C 1 -C 3 alkylthio (C 1 -C 2 )alkyl, C 1 -C 3 alkylsulfinyl (C 1 -C 2 )alkyl, C 1 -C 3 alkylsulfonyl (C 1 -C 2 )alkyl, C 3 -C 6 cycloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, phenyl, phenyl substituted with (Z) n1 , D-1, D-2 or D-23,
R 13 is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 3 alkoxy (C 1 -C 2 )alkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl or phenyl,
R 14 is hydrogen atom, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, C 1 -C 4 alkylcarbonyl, C 1 -C 4 haloalkylcarbonyl, C 3 -C 6 cycloalkylcarbonyl or C 1 -C 4 alkoxycarbonyl,
m is an integer of 0 to 5,
n1 is an integer of 1 to 5,
n2 is an integer of 0 to 3,
n3 is an integer of 0 to 4,
n4 is an integer of 0 to 2,
n5 is an integer of 0 or 1,
p is an integer of 0 to 2, and
q is an integer of 0 or 1.

2 . The method according to claim 1 , wherein in the parasite- and hygienic pest-controlling composition,
A 2 is C—H, A 3 and A 4 are independently of one another C—Y 2 or nitrogen atom, G is a heterocyclic ring of G-1, G-2, G-3, G-6 or G-7, X 1 is halogen atom, trifluoromethyl, pentafluoroethyl, trifluoromethoxy, —SF 5 or trifluoromethylthio, X 2 is hydrogen atom, halogen atom, cyano, methyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy, difluoromethylthio or trifluoromethylthio, X 3 is hydrogen atom, fluorine atom, chlorine atom, bromine atom, cyano or difluoromethoxy, Y 1 is hydrogen atom, halogen atom, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxymethyl, cyclopropyl, difluoromethoxy, methylthio, —N(R 7 )R 6 , —C(S)NH 2 or ethynyl, Y 2 is hydrogen atom, or when two Y 2 s are adjacent, the adjacent two Y 2 s may form 6-membered ring together with carbon atoms to which the two Y 2 s are bonded by forming —CH═CHCH═CH—, R 1 is difluoromethyl, trifluoromethyl or chlorodifluoromethyl, R 1a is hydrogen atom, halogen atom, methyl, methylthiomethyl, methylsulfinylmethyl or methylsulfonylmethyl, R 1b is hydrogen atom, or R 1b together with R 1a optionally forms C 2 -C 3 alkylidene, R 1c is methyl, R 2 is E-3, E-4, E-5, —CH 2 -(E-1) or —CH 2 -(E-9), R 3 is hydrogen atom, C 1 -C 3 alkyl, methyl substituted with R 11 , cyclopropyl, allyl, propargyl, —C(O)R 12 or —C(O)OR 13 , R 6 is hydrogen atom, methyl, C 1 -C 3 alkylcarbonyl or cyclopropylcarbonyl, R 7 is hydrogen atom or methyl, R 8 is methyl, R 9 is hydrogen atom, R 10 is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 3 alkoxy (C 1 -C 2 )alkyl, oxetan-3-yl or C 3 -C 4 alkynyl, R 11 is cyano, methoxy, ethoxy or —C(S)NH 2 , R 12 is C 1 -C 4 alkyl, C 1 -C 3 alkoxy (C 1 -C 2 )alkyl, C 3 -C 4 cycloalkyl, C 2 -C 4 alkenyl or C 2 -C 4 alkynyl, R 13 is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 3 alkoxy (C 1 -C 2 )alkyl, C 3 -C 4 alkenyl or C 3 -C 4 alkynyl, m is an integer of 0 to 4, and q is 1

Assignees

• Nissan Chemical Ind Ltd

Inventors

• Mita Takeshi
• Maizuru Yukihiro
• Toyama Ken-Ichi
• Iwasa Motoyoshi
• Imanaka Hotaka
• Matsui Hiroto

Classifications

• A01N43/80

  five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2 · CPC title

• C07D413/12 Primary

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

• A61K31/42

  Oxazoles · CPC title

• A01N43/36

  five-membered rings · CPC title

• A01N43/40

  six-membered rings · CPC title