Oxime-substituted amide compound and pest control agent

Patent metadata

Field	Value
Publication number	US-9434684-B2
Application number	US-201314414173-A
Country	US
Kind code	B2
Filing date	Jul 12, 2013
Priority date	Jul 12, 2012
Publication date	Sep 6, 2016
Grant date	Sep 6, 2016

Abstract

To provide a novel pesticide, especially a fungicide and a nematocide.
An oxime-substituted amide compound represented by the formula (I) or its salt, and a pesticide containing it:

wherein G 1 is a structure represented by G 1 -1 or the like, G 2 is a structure represented by G 2 -2 or the like:

W is an oxygen atom or the like, X 1 is a halogen atom, methyl, trifluoromethyl or the like, each of X 2 , X 3 , X 4 and X 5 is independently a hydrogen atom, a halogen atom or the like, each of Y 1 and Y 3 is independently a halogen atom, cyano, methyl, trifluoromethyl, C 2 -C 6 alkynyl or the like, each of Y 2 and Y 4 is independently a hydrogen atom, a halogen atom or the like, R 1 is C 1 -C 6 alkyl, C 1 -C 4 haloalkyl, (C 1 -C 4 )alkyl substituted with R 18 , C 3 -C 6 cycloalkyl, C 3 -C 6 alkenyl or the like, each of R 2 and R 3 is independently a hydrogen atom, methyl or the like, R 4 is a hydrogen atom or the like, R 18 is C 3 -C 6 cycloalkyl, phenyl, phenyl substituted with (Z) m or the like, Z is a halogen atom or the like, and m is an integer of 1, 2 or 3.

First claim

The invention claimed is:

1. An oxime-substituted amide compound represented by the formula (I), or its N-oxide or salt:

wherein:
G 1 is a structure represented by any one of G 1 -1 to G 1 -51:

G 2 is a structure represented by the formula G 2 -2:

W is an oxygen atom or a sulfur atom;
X 1 is a halogen atom, cyano, nitro, —SF 5 , C 1 -C 6 alkyl, (C 1 -C 6 )alkyl optionally substituted with R 6 , C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, —S(O) r R 7 , —N(R 9 )R 8 , —C(O)NH 2 , —C(S)NH 2 , tri(C 1 -C 6 alkyl)silyl, phenyl, phenyl substituted with (Z) m or D-3;
each of X 2 , X 3 , X 4 and X 5 is independently a hydrogen atom, a halogen atom, cyano, nitro, C 1 -C 6 alkyl, (C 1 -C 6 )alkyl optionally substituted with R 6 , C 3 -C 8 cycloalkyl, C 3 -C 5 halocycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, —OH, —OR 7 , −SH, —S(O) r R 7 , —N(R 9 )R 8 , C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, —C(O)NH 2 , —C(S)NH 2 , phenyl, phenyl substituted with (Z) m , D-2 or D-32,
provided that when G 1 is a structure represented by G 1 -27 and X 1 is dihalomethyl, X 2 is a hydrogen atom;
each of Y 1 and Y 3 is independently a hydrogen atom, a halogen atom, cyano, nitro, —SCN, —SF 5 , C 1 -C 8 alkyl, (C 1 -C 6 )alkyl optionally substituted with R 6 , C 3 -C 10 cycloalkyl, (C 3 -C 10 )cycloalkyl optionally substituted with R 6 , E-1 to E-22, C 2 -C 6 alkenyl, (C 2 -C 6 )alkenyl optionally substituted with R 6 , C 5 -C 10 cycloalkenyl, C 5 -C 10 halocycloalkenyl, C 2 -C 6 alkynyl, (C 2 -C 6 )alkynyl optionally substituted with R 6 , —OH, —OR 7 , —OS(O) 2 R 7 , —SH, —S(O) r R 7 , —N(R 9 )R 8 , —N═C(R 9a )R 8a , —C(O)R 10 , —C(R 10 )═NOH, —C(R 10 )═NOR 11 , M-3, M-13, M-30, —C(O)OH, —C(O)OR 11 , —C(O)SR 11 , —C(O)N(R 13 )R 12 , M-7, M-17, M-23, M-26, —C(S)OR 11 , —C(S)SR 11 , —C(S)N(R 13 )R 12 , M-9, M-19, M-23, M-24, M-28, M-25, M-29, —S(O) 2 OR 11 , —S(O) 2 N(R 13 )R 12 , —Si(R 14a )(R 14b )R 14 ), phenyl, phenyl substituted with (Z) m , or D-1 to D-38;
each of Y 2 and Y 4 is independently a hydrogen atom, a halogen atom, cyano, nitro, —SCN, —SF 5 , C 1 -C 6 alkyl, (C 1 -C 6 )alkyl optionally substituted with R 6 , C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, —OH, —SH, —S(O) r R 7 , —NH 2 , C 1 -C 6 alkylamino, di(C 1 -C 6 alkyl)amino, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 1 -C 6 alkoxycarbonyl, —C(O)NH 2 or —C(S)NH 2 ,
or, Y 1 , Y 2 , Y 3 and Y 4 represent that Y 1 or Y 3 and Y 2 , or Y 3 and Y 4 , together form —CH 2 CH 2 CH 2 —, —CH 2 CH 2 O—, —CH 2 OCH 2 —, —OCH 2 O—, —CH 2 CH 2 CH 2 CH 2 —, —CH 2 CH 2 S—, —CH 2 SCH 2 —, —SCH 2 S—, —CH 2 CH 2 N(R 5 )—, —CH 2 N(R 5 )CH 2 —, —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—, —CH 2 CH═CH—, —N(R 5 )N═CH—, —OCH 2 CH═CH—, —CH═CHCH═CH—, —CH═CHCH═N—, —CH═CHN═CH—, —CH═NCH═N— or —N═CHCH═N— to form a 5-membered ring or a 6-membered ring together with the carbon atoms attached to Y 1 , Y 2 , Y 3 and Y 4 , wherein hydrogen atoms on the respective ring-constituting carbon atoms are optionally substituted with a halogen atom, cyano, nitro, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl, and further, when G 1 is a structure represented by G 1 -1, G 1 -9, G 1 -10, G 1 -12, G 1 -13, G 1 -16 to G 1 -20, G 1 -22 to G 1 -24, G 1 -26, G 1 -27, G 1 -30, G 1 -32, G 1 -35, G 1 -38, G 1 -40 or G 1 -42 to G 1 -50, Y 1 and Y 2 , Y 2 and Y 3 , or Y 3 and Y 4 , together optionally form —OCH═CH—, —SCH═CH—, —N(R 5 )CH═CH—, —OCH═N—, —SCH═N— or —N(R 5 )CH═N— to form a 5-membered ring together with the carbon atoms attached to Y 1 , Y 2 , Y 3 and Y 4 , wherein hydrogen atoms on the respective ring-constituting carbon atoms are optionally substituted with a halogen atom, cyano, nitro, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;
D-1 to D-38 are aromatic heterocyclic rings represented by the following structural formulae, respectively:

E-1 to E-22 are saturated heterocyclic rings represented by the following structural formulae, respectively:

Z is a halogen atom, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy(C 1 -C 4 )alkyl, C 1 -C 4 haloalkoxy(C 1 -C 4 )alkyl, C 1 -C 4 alkylthio(C 1 -C 4 )alkyl, C 1 -C 4 haloalkylthio(C 1 -C 4 )alkyl, C 1 -C 4 alkylsulfinyl(C 1 -C 4 )alkyl, C 1 -C 4 haloalkylsulfinyl(C 1 -C 4 )alkyl, C 1 -C 4 alkylsulfonyl(C 1 -C 4 )alkyl, C 1 -C 4 haloalkylsulfonyl(C 1 -C 4 )alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, —OH, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylsulfonyloxy, haloalkylsulfonyloxy, alkylthio, C 1 -C 4 haloalkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 4 alkylamino, di(C 1 -C 4 alkyl)amino, alkoxycarbonyl, haloalkoxycarbonyl, —C(O)NH 2 , C 1 -C 4 alkylaminocarbonyl, di(C 1 -C 4 alkyl)aminocarbonyl, —C(S)NH 2 , —S(O) 2 NH 2 or phenyl;
when m or n is an integer of at least 2, the respective Z's are identical with or different from one another, and when there are two neighboring Z's, the two neighboring Z's optionally form —CH 2 CH 2 CH 2 —, —CH 2 CH 2 O—, —CH 2 OCH 2 —, —OCH 2 O—, —CH 2 CH 2 S—, —CH 2 SCH 2 —, —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—, —CH 2 CH 2 CH 2 S—, —OCH 2 CH 2 S— or —CH═CH—CH═CH— to form a 5-membered ring or a 6-membered ring together with the carbon atoms attached to the two Z's, wherein hydrogen atoms on the respective ring-constituting carbon atoms are optionally substituted with a halogen atom, a cyano group, a nitro group, a methyl group, a trifluoromethyl group, a methoxy group or a methylthio group;
R 1 is C 1 -C 8 alkyl, (C 1 -C 8 )alkyl optionally substituted with R 18 , C 3 -C 10 cycloalkyl, C 3 -C 10 halocycloalkyl, E-2 to E-8, E-14 to E-18, E-21, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 5 -C 10 cycloalkenyl, C 5 -C 10 halocycloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, phenyl(C 3 -C 6 )alkynyl, phenyl or phenyl substituted with (Z) m ;
R 2 is a hydrogen atom, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, alkoxy(C 1 -C 4 )alkyl, C 1 -C 4 alkylthio(C 1 -C 4 )alkyl, C 1 -C 4 alkylsulfinyl(C 1 -C 4 )alkyl, C 1 -C 4 alkylsulfonyl-(C 1 -C 4 )alkyl, C 3 -C 6 cycloalkyl or phenyl, or optionally forms a ring together with R 3 ,
R 3 is a hy

Assignees

• Nissan Chemical Ind Ltd

Inventors

• Iwasa Motoyoshi
• Tsuji Keisuke
• Tomizawa Mitsutaka
• Mita Takeshi
• Kuwahara Hidehito
• Asahi Miho
• Imanaka Hotaka

Classifications

• A61P31/10

  Antimycotics · CPC title

• A61P31/04

  Antibacterial agents · CPC title

• A61P33/02

  Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis · CPC title

• A61P33/00

  Antiparasitic agents · CPC title

• A61P33/10

  Anthelmintics · CPC title