IP Library Granted Patent US 10,136,640
Granted Patent B2
US 10,136,640 · App. 15/537,301 · Granted Nov 27, 2018

Ketone or oxime compound, and herbicide

Inventors: Akira Numata (Funabashi, JP); Yuji Iwawaki (Funabashi, JP); Yuki Furukawa (Funabashi, JP); Yuri Yoshino (Funabashi, JP); Yuuki Miyakado (Shiraoka, JP); Takamasa Furuhashi (Shiraoka, JP); Takao Miyazaki (Shiraoka, JP)
Assignee: NISSAN CHEMICAL CORPORATION
A01N35/10A01N35/06A01N37/42A01N41/06A01N43/10A01N43/40A01N43/50A01N43/56A01N43/653A01N43/84A01N55/00C07C49/747C07C69/78C07C251/40C07C311/29C07D213/53C07D231/12C07D233/61C07D249/08C07D295/135C07D333/22C07F7/0818
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Quick Facts
Patent No.
US 10,136,640
App. No.
15/537,301
Granted
Nov 27, 2018
Kind
B2
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 including the compound or salt thereof.

Claims (107)

1. A 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 NOR 7 ;

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 7 is a hydrogen atom, C 1-8 alkyl, (C 1-6 ) alkyl arbitrarily substituted with R 15b , C 3-8 cycloalkyl, (C 3-8 ) cycloalkyl arbitrarily substituted with R 15b , C 2-6 alkenyl, (C 2-6 ) alkenyl arbitrarily substituted with R 15b , C 3-8 cycloalkenyl, (C 3-8 ) cycloalkenyl arbitrarily substituted with R 15b , C 2-6 alkynyl, (C 2-6 ) alkynyl arbitrarily substituted with R 15b , phenyl, or phenyl substituted with (Z 1 ) q1 ;

R 8a , R 8b , R 9a , and R 9b are each independently a hydrogen atom, cyano, nitro, C 1-6 alkyl, halo (C 1-6 ) alkyl, —OR 16a , —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 15b is a halogen atom, cyano, C 3-8 cycloalkyl, halo (C 3-8 ) cycloalkyl, —OR 16b , —S(O) r1 R 16b , —C(O)OR 16b , —C(O)N(R 18b )R 19b , —C(═NOR 16b )R 17b , —N(R 18b )R 19b , —Si(R 32a )(R 32b )R 32c , phenyl, phenyl substituted with (Z 1 ) q1 , D1-32, D1-33, D1-34, D1-36, D1-37, D1-38, D1-81, or D1-84, or when two R 15b s are substituents on a same carbon, the two R 15b s optionally form oxo, thioxo, imino, C 1-6 alkylimino, C 1-6 alkoxyimino, or C 1-6 alkylidene, together with each other;

R 16 , R 16a , R 16b , R 17 , R 17a , R 17b , R 18a , and R 19a are each independently a hydrogen atom or C 1-6 alkyl;

R 18b and R 19b are each independently a hydrogen atom, C 1-6 alkyl, or (C 1-6 ) alkyl arbitrarily substituted with R 20 , or R 18b optionally forms a 3- to 8-membered ring together with a nitrogen atom to which R 18b and R 19b are bonded by forming a C 2-7 alkylene chain or a C 2-7 alkenylene chain together with R 19b , 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 oxo or thioxo;

R 20 is phenyl or phenyl substituted with (Z 1 ) q1 ;

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, when g2 is 2, g3 is an integer of 2 or 3, or g4 is an integer of 2, 3, or 4, 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 is 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 3-8 cycloalkenyl, (C 3-8 ) cycloalkenyl 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, and when q is an integer of 2, 3, 4, or 5, each Z is the same as or different from each other;

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, and when q1 is an integer of 2, 3, 4, or 5, 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 , when q2 is an integer of 2, 3, 4, or 5, 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, and when q3 is an integer of 2, 3, 4, or 5, 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 , or —C(O)R 37 ;

R 35 is a halogen atom, C 1-6 alkoxy, C 1-6 alkylthio, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, or phenyl;

R 36 is C 1-6 alkyl;

R 37 is a hydrogen atom, C 1-6 alkyl, phenyl, or phenyl substituted with (Z 2 ) q2 ;

R 41 is a hydrogen atom, C 1-6 alkyl, (C 1-6 ) alkyl arbitrarily substituted with R 45 , phenyl, phenyl substituted with (Z 3 ) q3 , D1-32, D1-33, or D1-34;

R 42 is a hydrogen atom or C 1-6 alkyl;

R 43 and R 44 are each independently a hydrogen atom, C 1-6 alkyl, C 1-6 alkoxycarbonyl, or C 1-6 alkylcarbonyl;

R 45 is a halogen atom, C 3-8 cycloalkyl, —OH, C 1-6 alkoxy, C 1-10 alkoxycarbonyl, —Si(R 32a )(R 32b )R 32c , phenyl, phenyl substituted with (Z 3 ) q3 , D1-32, D1-33, or D1-34, or when two R 45 s are substituents on a same carbon, the two R 45 s optionally form oxo, thioxo, imino, C 1-6 alkylimino, C 1-6 alkoxyimino, or C 1-6 alkylidene, together with each other;

R 51 is a hydrogen atom, C 1-6 alkyl, halo (C 1-6 ) alkyl, phenyl, phenyl arbitrarily substituted with a halogen atom, or D1-39;

R 51a and R 52 are each independently a hydrogen atom or C 1-6 alkyl;

R 53 and R 54 are each independently a hydrogen atom, C 1-6 alkyl, or C 1-6 alkylcarbonyl;

f5 is an integer of 0, 1, 2, 3, 4, or 5;

f7 is an integer of 0, 1, 2, 3, 4, 5, 6, or 7;

g1 and p are each independently an integer of 0 or 1;

g2, m, n, r1, r2, and r3 are each independently an integer of 0, 1, or 2;

g3 is an integer of 0, 1, 2, or 3;

g4 is an integer of 0, 1, 2, 3, or 4; and

q, q1, q2, and q3 are each independently an integer of 1, 2, 3, 4, or 5.

2. The oxime compound or a salt thereof according to claim 1 , wherein

B is a ring of either B-1-a or B-2-a; and

Z a , Z c and Z e 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.

3. The oxime compound or the salt thereof according to claim 2 , wherein

A is a hydrogen atom, C 1-6 alkyl, (C 1-6 ) alkyl arbitrarily substituted with R 5 , C 3-8 cycloalkyl, C 2-6 alkenyl, (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(O)SR 1 , —C(S)OR 1 , —C(O)R 2 , —C(O)N(R 4 )R 3 , —C(S)N(R 4 )R 3 , or —S(O) 2 N(R 4 )R 3 ;

R 1 is C 1-8 alkyl, (C 1-6 ) alkyl arbitrarily substituted with R 5 , C 3-8 cycloalkyl, C 2-6 alkenyl, phenyl, or phenyl substituted with (Z 2 ) q2 ;

R 2 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 , —C(═NOR 31 )R 32 , phenyl, phenyl substituted with (Z 2 ) q2 , D1-5, D1-6, D1-8, D1-10, or D1-81;

R 3 is C 1-6 alkyl, (C 1-6 ) alkyl arbitrarily substituted with R 5 , C 2-6 alkenyl, phenyl, or phenyl substituted with (Z 2 ) q2 , or R 3 forms a 5- to 6-membered ring together with a nitrogen atom to which R 3 and R 4 are bonded by forming a C 4 or C 5 alkylene chain together with R 4 , and at this time, the alkylene chain optionally contains one oxygen atom or nitrogen atom and is optionally substituted with C 1-6 alkyl;

R 4 is C 1-6 alkyl, C 2-6 alkenyl, or phenyl;

R 5 is a halogen atom, cyano, 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 , or D1-1, or when two R 5 s are substituents on a same carbon, the two R 5 s optionally form C 1-6 alkoxyimino 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 2-6 alkenyl, —C(═NOR 16 )R 17 , phenyl, phenyl substituted with (Z 1 ) q1 or, D1-32;

R 7 is a hydrogen atom, C 1-7 alkyl, (C 1-6 ) alkyl arbitrarily substituted with R 15b , C 3-8 cycloalkyl, C 2-6 alkenyl, C 3-8 cycloalkenyl, (C 2-6 ) alkenyl arbitrarily substituted with R 15b , C 2-6 alkynyl, or phenyl;

R 8a is a hydrogen atom, C 1-6 alkyl, halo (C 1-6 ) alkyl, —C(O)OR 16a , —C(═NOR 16a )R 17a , or phenyl substituted with (Z 1 ) q1 ;

R 9a is a hydrogen atom or C 1-6 alkyl;

R 8b and R 9b are hydrogen atoms;

R 12 is a hydrogen atom;

R 15 is a halogen atom, C 3-8 cycloalkyl, or —OR 16 ;

R 15b is a halogen atom, cyano, C 3-8 cycloalkyl, halo (C 3-8 ) cycloalkyl, —OR 16b , —S(O) r1 R 16b , —C(O)OR 16b , —C(O)N(R 18b )R 19b , —C(—NOR 16b )R 17b , —N(R 18b )R 19b , —Si(R 32a )(R 32b )R 32c , phenyl, phenyl substituted with (Z 1 ) q1 , D1-32, or D1-84;

R 16 , R 16a , R 17 , R 17a , and R 17b are each independently C 1-6 alkyl;

R 18b is a hydrogen atom, C 1-6 alkyl, or (C 1-6 ) alkyl arbitrarily substituted with R 20 , or R 18b forms a 6-membered ring together with a nitrogen atom to which R 18b and R 19b are bonded by forming a C 5 alkylene chain together with R 19b , and at this time, the alkylene chain contains one oxygen atom;

R 19b is a hydrogen atom or C 1-6 alkyl;

R 20 is phenyl substituted with (Z 1 ) q1 ;

X 1 is a halogen atom, C 1-6 alkyl, halo (C 1-6 ) alkyl, or C 3-8 cycloalkyl, g3 is an integer of 2, and further the two adjacent X 1 s 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, one hydrogen atom bonded to each carbon atom forming the ring is arbitrarily substituted with a halogen atom;

X 1a is C 1-6 alkyl;

Z a , Z c , and Z e are each independently a hydrogen atom, a halogen atom, cyano, nitro, C 1-6 alkyl, C 3-8 cycloalkyl, 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 , D1-2, D1-7, D1-11, D1-22, D1-32, D1-33, D1-34, or D1-37,

Z 1 is a halogen atom, nitro, C 1-6 alkyl, halo (C 1-6 ) alkyl, C 1-6 alkoxy, or C 1-6 alkoxycarbonyl, and when q1 is an integer of 2, 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 , or —C(O)N(R 54 )R 53 , when q2 is an integer of 2 or 3, each Z 2 is the same as or different from each other, and further when the 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—, and at this time, one hydrogen atom bonded to each carbon atom forming the ring is arbitrarily substituted with a halogen atom;

Z 3 is a halogen atom, C 1-6 alkyl, halo (C 1-6 ) alkyl, C 1-6 alkoxy, halo (C 1-6 ) alkoxy, or C 1-6 alkylthio, and when q3 is an integer of 2 or 3, each Z 3 is the same as or different from each other;

R 31 is C 1-6 alkyl, (C 1-6 ) alkyl arbitrarily substituted with R 35 , —C(O)R 37 , phenyl, phenyl substituted with (Z 2 ) q2 , or naphthyl;

R 32 is C 1-6 alkyl or (C 1-6 ) alkyl arbitrarily substituted with R 35 ;

R 33 is —C(O)R 37 ;

R 34 is C 1-6 alkyl;

R 35 is a halogen atom, C 1-6 alkylthio, or phenyl;

R 37 is C 1-6 alkyl or phenyl;

R 41 is a hydrogen atom, C 1-6 alkyl, (C 1-6 ) alkyl arbitrarily substituted with R 45 , phenyl, or D1-32;

R 42 is C 1-6 alkyl;

R 43 is C 1-6 alkoxycarbonyl;

R 44 is a hydrogen atom;

R 45 is a halogen atom, C 3-8 cycloalkyl, —OH, C 1-6 alkoxy, C 1-10 alkoxycarbonyl, —Si(R 32a )(R 32b )R 32c , phenyl, or D1-34;

R 51 is C 1-6 alkyl, halo (C 1-6 ) alkyl, phenyl arbitrarily substituted with a halogen atom, or D1-39;

R 51a is C 1-6 alkyl;

R 53 and R 54 are each independently C 1-6 alkyl;

g2 is an integer of 0, 1, or 2;

g3 and r1 are each independently an integer of 0, 1, or 2;

g4, m, and n are each independently an integer of 0 or 1;

f7, p, and r3 are 0;

q1 is an integer of 1 or 2;

q2 is an integer of 1, 2, or 3;

q3 is an integer of 1, 2, or 3; and

r2 is an integer of 0 or 2.

4. The oxime compound or the salt according to claim 3 , wherein

B is B-1-a;

Z a is a halogen atom, C 1-6 alkyl, C 1-6 alkoxy, or C 1-6 alkylthio;

Z c is a hydrogen atom, a halogen atom, cyano, nitro, C 1-6 alkyl, C 3-8 cycloalkyl, 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 , —(═NOR 41 )R 42 , —N(R 44 )R 43 , phenyl, phenyl substituted with (Z 3 ) q3 , D1-2, D1-7, D1-11, D1-22, D1-32, D1-33, D1-34, or D1-37;

Z e is a halogen atom, C 1-6 alkyl, or C 1-6 alkoxy;

X 1 is a halogen atom or halo (C 1-6 ) alkyl; and

g3 is an integer of 0 or 1.

5. An agricultural chemical comprising:

one or more of compounds selected from the oxime compound or the salt thereof as claimed in claim 1 as an active component.

6. A herbicide comprising:

one or more of compounds selected from the oxime compound or the salt thereof as claimed in claim 1 as an active component.

Assignments (2)
CHANGE OF NAME Recorded Oct 16, 2018
From: NISSAN CHEMICAL INDUSTRIES, LTD.
To: NISSAN CHEMICAL CORPORATION
Reel/Frame 047870/0903 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 16, 2017
From: NUMATA, AKIRA; IWAWAKI, YUJI; FURUKAWA, YUKI; YOSHINO, YURI; MIYAKADO, YUUKI; FURUHASHI, TAKAMASA; MIYAZAKI, TAKAO
To: NISSAN CHEMICAL INDUSTRIES, LTD.
Reel/Frame 042738/0828 →
Priority Claims (4)
JP 2014-255973 · Dec 18, 2014 · national
JP 2015-029704 · Feb 18, 2015 · national
JP 2015-083620 · Apr 15, 2015 · national
JP 2015-136991 · Jul 8, 2015 · national
Continuity (1)
Related Publication 20170347647A1 · Dec 7, 2017