Ketone or oxime compound, and herbicide

Patent metadata

Field	Value
Publication number	US-11000033-B2
Application number	US-201916662085-A
Country	US
Kind code	B2
Filing date	Oct 24, 2019
Priority date	Dec 18, 2014
Publication date	May 11, 2021
Grant date	May 11, 2021

Abstract

There is provided novel agricultural chemicals, in particular herbicides. A ketone or oxime compound or a salt thereof of Formula (1):

wherein B is a ring of any one of B-1, B-2, or B-3, Q is an oxygen atom, a sulfur atom, NOR 7 , etc., R 6 is a hydrogen atom, C 1-6 alkyl, etc., R 7 is a hydrogen atom, C 1-6 alkyl, etc., R 8a , R 8b , R 9a , R 9b , R 10 , R 11 , R 12 , R 13 , and R 14 are each independently a hydrogen atom, C 1-6 alkyl, etc., m is an integer of 1 or 2, n is an integer of 0, 1 or 2; and a herbicide comprising the compound or salt thereof.

First claim

The invention claimed is:

1. A ketone compound or a salt thereof of Formula (1):

wherein B is a ring of B-1-a or B-2-a;

Q is an oxygen atom;
A is a hydrogen atom, C 1-6 alkyl, (C 1-6 ) alkyl arbitrarily substituted with R 5 , C 3-8 cycloalkyl, (C 3-8 ) cycloalkyl arbitrarily substituted with R 5 , C 2-6 alkenyl, C 3-8 cycloalkenyl, (C 3-8 ) cycloalkenyl arbitrarily substituted with R 5 , (C 2-6 ) alkenyl arbitrarily substituted with R 5 , C 2-6 alkynyl, (C 2-6 ) alkynyl arbitrarily substituted with R 5 , —S(O) r2 R 1 , —C(O)OR 1 , —C(S)OR 1 , —C(O)SR 1 , —C(S)SR 1 , —C(O)R 2 , —C(S)R 2 , —C(O)N(R 4 )R 3 , —C(S)N(R 4 )R 3 , —S(O) 2 N(R 4 )R 3 , —P(O)(OR 1 ) 2 , or —P(S)(OR 1 ) 2 ;
R 1 is C 1-8 alkyl, (C 1-6 ) alkyl arbitrarily substituted with R 5 , C 3-8 cycloalkyl, (C 3-8 ) cycloalkyl arbitrarily substituted with R 5 , C 2-6 alkenyl, (C 2-6 ) alkenyl arbitrarily substituted with R 5 , C 3-8 cycloalkenyl, (C 3-8 ) cycloalkenyl arbitrarily substituted with R 5 , C 2-6 alkynyl, (C 2-6 ) alkynyl arbitrarily substituted with R 5 , phenyl, or phenyl substituted with (Z 2 ) q2 ;
R 2 is a hydrogen atom, C 1-8 alkyl, (C 1-6 ) alkyl arbitrarily substituted with R 5 , C 3-8 cycloalkyl, (C 3-8 ) cycloalkyl arbitrarily substituted with R 5 , C 2-6 alkenyl, (C 2-6 ) alkenyl arbitrarily substituted with R 5 , C 3-8 cycloalkenyl, (C 3-8 ) cycloalkenyl arbitrarily substituted with R 5 , C 2-6 alkynyl, (C 2-6 ) alkynyl arbitrarily substituted with R 5 , —C(═NOR 31 )R 32 , phenyl, phenyl substituted with (Z 2 ) q2 , naphthyl, naphthyl substituted with (Z 2 ) q2 , D1-1 to D1-42, D1-81, or D1-84;
R 3 and R 4 are each independently a hydrogen atom, C 1-6 alkyl, (C 1-6 ) alkyl arbitrarily substituted with R 5 , C 3-8 cycloalkyl, (C 3-8 ) cycloalkyl arbitrarily substituted with R 5 , C 2-6 alkenyl, (C 2-6 ) alkenyl arbitrarily substituted with R 5 , C 3-8 cycloalkenyl, (C 3-8 ) cycloalkenyl arbitrarily substituted with R 5 , C 2-6 alkynyl, (C 2-6 ) alkynyl arbitrarily substituted with R 5 , phenyl, phenyl substituted with (Z 2 ) q2 , D1-32, D1-33 or D1-34, or R 3 optionally forms a 3- to 8-membered ring together with a nitrogen atom to which R 3 and R 4 are bonded by forming a C 2-7 alkylene chain or a C 2-7 alkenylene chain together with R 4 , and at this time, the alkylene chain or the alkenylene chain optionally contains one oxygen atom, sulfur atom, or nitrogen atom and optionally substituted with C 1-6 alkyl, oxo, or thioxo;
R 5 is a halogen atom, cyano, nitro, C 3-8 cycloalkyl, —OR 31 , —S(O) r2 R 31 , —C(O)OR 31 , —C(O)R 32 , —N(R 34 )R 33 , —Si(R 32a )(R 32b )R 32c , phenyl, phenyl substituted with (Z 2 ) q2 , D1-1, D1-32, D1-33, or D1-34, or when two R 5 s are substituents on a same carbon, the two R 5 s optionally form oxo, thioxo, imino, C 1-6 alkylimino, C 1-6 alkoxyimino, or C 1-6 alkylidene, together with each other;
R 6 is a hydrogen atom, C 1-6 alkyl, (C 1-6 ) alkyl arbitrarily substituted with R 15 , C 3-8 cycloalkyl, (C 3-8 ) cycloalkyl arbitrarily substituted with R 15 , C 2-6 alkenyl, (C 2-6 ) alkenyl arbitrarily substituted with R 15 , C 3-8 cycloalkenyl, (C 3-8 ) cycloalkenyl arbitrarily substituted with R 15 , C 2-6 alkynyl, (C 2-6 ) alkynyl arbitrarily substituted with R 15 , —C(═NOR 16 )R 17 , phenyl, phenyl substituted with (Z 1 ) q1 , D1-32, D1-33, D1-34, D1-36, D1-37, or D1-38;
R 8a , R 8b , R 9a , are each independently a hydrogen atom, cyano, nitro, C 1-6 alkyl; halo (C 1-6 ) alkyl, —OR 16 , —S(O) r1 R 16a , —C(O)OR 16a , —C(O)R 17a , —C(O)N(R 19a )R 18a , —C(═NOR 16a )R 17a , phenyl, or phenyl substituted with (Z 1 ) q1 ;
R 10 , R 11 , and R 12 are each independently a hydrogen atom or C 1-6 alkyl;
R 15 is a halogen atom, cyano, C 3-8 cycloalkyl, —OR 16 , —S(O) r1 R 16 , phenyl, phenyl substituted with (Z 1 ) q1 , D1-7, D1-11, D1-22, D1-32, D1-33, or D1-34;
R 16 , R 16a , R 17 , R 17a , R 18a , and R 19a are each independently a hydrogen atom or C 1-6 alkyl;
D1-1 to D1-42, D1-81, and D1-84 each are a ring of the following structure;

X 1 is a halogen atom, cyano, nitro, C 1-6 alkyl, halo (C 1-6 ) alkyl, or C 3-8 cycloalkyl, provided that when more than one X 1 is present, each X 1 is the same as or different from each other, and further when two X 1 s are adjacent, the two adjacent X 1 s optionally form a 6-membered ring together with carbon atoms to which each X 1 is bonded by forming—CH═CHCH═CH—, and at this time, the hydrogen atom bonded to each carbon atom forming the ring is optionally substituted with a halogen atom, cyano, nitro, C 1-6 alkyl, halo (C 1-6 ) alkyl, C 1-6 alkoxy, C 1-6 alkylthio, C 1-6 alkylsulfinyl, or C 1-6 alkylsulfonyl;
X 1a is a hydrogen atom or C 1-6 alkyl;
X 1b is C 1-6 alkyl;
Z a and Z c are each independently a hydrogen atom, a halogen atom, cyano, nitro, C 1-6 alkyl, (C 1-6 ) alkyl arbitrarily substituted with R 45 , C 3-8 cycloalkyl, (C 3-8 ) cycloalkyl arbitrarily substituted with R 45 , C 2-6 alkenyl, (C 2-6 ) alkenyl arbitrarily substituted with R 45 , C 2-6 alkynyl, (C 2-6 ) alkynyl arbitrarily substituted with R 45 , —OR 41 , —S(O) r3 R 41 , —C(O)OR 41 , —C(O)R 42 , —C(═NOR 41 )R 42 , N(R 44 )R 43 , phenyl, phenyl substituted with (Z 3 ) q3 , D1-1, D1-2, D1-7, D1-10, D1-11, D1-22, D1-32, D1-33, D1-34, D1-36, D1-37, or D1-38;
Z e is a methyl group;
Z 1 is a halogen atom, cyano, nitro, C 1-6 alkyl, halo (C 1-6 ) alkyl, C 1-6 alkoxy, or C 1-6 alkoxycarbonyl, provided that when more than one Z 1 is present, each Z 1 is the same as or different from each other;
Z 2 is a halogen atom, cyano, nitro, C 1-6 alkyl, halo (C 1-6 ) alkyl, —OR 51 , —S(O) r2 R 51 , —C(O)OR 51a , —C(O)R 52 , —C(O)N(R 54 )R 53 , —C(S)N(R 54 )R 53 , or —N(R 54 )R 53 , provided that when more than one Z 2 is present, each Z 2 is the same as or different from each other, and further when two Z 2 s are adjacent, the two adjacent Z 2 s optionally form a 6-membered ring together with carbon atoms to which each Z 2 is bonded by forming—N═CHCH═CH—, —CH═NCH═CH—, —N═NCH═CH—, —CH═NN═CH—, —N═CHCH═N—, or —N═CHN═CH—, and at this time, the hydrogen atom bonded to each carbon atom forming the ring is optionally substituted with a halogen atom, cyano, nitro, C 1-6 alkyl, halo (C 1-6 ) alkyl, C 1-6 alkoxy, C 1-6 alkylthio, C 1-6 alkylsulfinyl, or C 1-6 alkylsulfonyl;
Z 3 is a halogen atom, cyano, nitro, C 1-6 alkyl, halo (C 1-6 ) alkyl, C 1-6 alkoxy, halo (C 1-6 ) alkoxy, C 1-6 alkylthio, C 1-6 alkylsulfinyl, or C 1-6 alkylsulfonyl, provided that when more than one Z 3 is present, each Z 3 is the same as or different from each other;
R 31 is a hydrogen atom, C 1-6 alkyl, (C 1-6 ) alkyl arbitrarily substituted with R 35 , —C(O)R 37 , phenyl, phenyl substituted with (Z 2 ) q2 , naphthyl, or naphthyl substituted with (Z 2 ) q2 ;
R 32 is a hydrogen atom, C 1-6 alkyl, or (C 1-6 ) alkyl arbitrarily substituted with R 35 ;
R 32a , R 32b , and R 32c are each independently C 1-6 alkyl;
R 33 and R 34 are each independently a hydrogen atom, C 1-6 alkyl, —C(O)OR 36

Assignees

• Nissan Chemical Corp

Inventors

• Numata Akira
• Iwawaki Yuji
• Furukawa Yuki
• Yoshino Yuri
• Miyakado Yuuki
• Furuhashi Takamasa
• Miyazaki Takao

Classifications

• C07D213/53 Primary

  Nitrogen atoms · CPC title

• C07C251/40

  to carbon atoms of an unsaturated carbon skeleton · CPC title

• C07D213/04

  having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom · CPC title

• C07F7/081

  comprising at least one atom selected from the elements N, O, halogen, S, Se or Te · CPC title

• A01N33/16

  containing nitrogen-to-oxygen bonds · CPC title