TECHNICAL FIELD
[0001] The present invention relates to a novel ketone or oxime compound or a salt thereof, and agricultural chemicals, in particular herbicides, containing the ketone or oxime compound or the salt thereof as an active component. The agricultural chemical in the present invention means an insecticide/acaricide, a nematicide, a herbicide, and a bactericide in agricultural and horticultural fields.
BACKGROUND ART
[0002] For example, certain types of ketone or oxime compounds have been described in Patent Documents 1 to 4. The ketone or the oxime compound according to the present invention, however, has not been described at all. Prior Art Documents Patent Documents
[0003] Patent Document 1: WO2001/017972 Pamphlet
Problem to be Solved by the Invention
An object of the present invention is to provide a chemical substance that

surely shows effect on various weeds in a low application amount of the chemical substance, has reduced land pollution and reduced influence on succeeding crops, and high safety, and is useful as an active component of herbicides. Means for Solving the Problem
[0005] As a result of intensive investigation for solving the problem, the inventors of the present invention have found that a novel ketone or oxime compound of Formula (1) below according to the present invention has excellent herbicidal activity as a herbicide and high safety against target crops as well as has almost no adverse effect on non-target creatures such as mammals, fish, and beneficial insects, and is an extremely useful compound, and thus have accomplished the present invention.
[0006] More specifically, the present invention relates to the following [1] to [151].
[0007]
[wherein B is a ring of any one of B-l, B-2, or B-3;
Aketone or oxime compound or a salt thereof of Formula (1):


B-l B-2 B-3
Q is an oxygen atom, a sulfur atom, or NOR ;
A is a hydrogen atom, Ci_6 alkyl, (Ci_6) alkyl arbitrarily substituted with R5, C3-8 cycloalkyl, (C3-8) cycloalkyl arbitrarily substituted with R5, C2-6 alkenyl, C3-8

3 cycloalkenyl, (C3-8) cycloalkenyl arbitrarily substituted with R5, (C2-6) alkenyl arbitrarily
substituted with R5, C2-6 alkynyl, (C2-6) alkynyl arbitrarily substituted with R5, -S(0)i2R-C(0)OR\ -C^OR1, -C(0)SR1, -C(S)SR\ -C(0)R2, -C(S)R2, -C(0)N(R4)R3,
-C(S)N(R4)R3, -S(0)2N(R4)R3, -P(0)(OR1)2, or -PfSXOR1^;
5 R! is Ci_8 alkyl, (Ci^) alkyl arbitrarily substituted with R5, C3-8 cycloalkyl, (C3-8)
cycloalkyl arbitrarily substituted with R5, C2-6 alkenyl, (C2~6) alkenyl arbitrarily
substituted with R5, C3-8 cycloalkenyl, (C3-8) cycloalkenyl arbitrarily substituted with R5,
C2-6 alkynyl, (C2-6) alkynyl arbitrarily substituted with R5, phenyl, or phenyl substituted
with (Z2)q2;
10 R is a hydrogen atom, Cj.g alkyl, (Ci^) alkyl arbitrarily substituted with R , C3-8
cycloalkyl, (C3-3) cycloalkyl arbitrarily substituted with R5, C2-6 alkenyl, (C2^) alkenyl arbitrarily substituted with R5, C3-8 cycloalkenyl, (C3.it) cycloalkenyl arbitrarily substituted with R% C2-6 alkynyl, (C2-6) alkynyl arbitrarily substituted with R5, -C(=NOR31)R32, phenyl, phenyl substituted with (Z2)q2, naphthyl, naphthyl substituted
15 with (Z2)q2, Dl-1 to Dl-42, Dl-81, or Dl-84;
R3andR4 are each independently a hydrogen atom, Ci^ alkyl, (C1-6) alkyl arbitrarily substituted with R5, C3-8 cycloalkyl, (C3.8) cycloalkyl arbitrarily substituted with R5, C2-6 alkenyl, (C2-6) alkenyl arbitrarily substituted with R5, C3-8 cycloalkenyl, (C3-8) cycloalkenyl arbitrarily substituted with R5, C2-6 alkynyl, (C2-6) alkynyl arbitrarily
20 substituted with R5, phenyl, phenyl substituted with (Z2)q2, Dl-32, Dl-33 or Dl-34, or R3 optionally forms a 3- to 8-membered ring together with a nitrogen atom to which R3 and R are bonded by forming a C2-7 alkylene chain or a C2-7 alkenylene chain together with R4, 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 C1-6 alkyl,
25 oxo, orthioxo;
R5 is a halogen atom, cyano, nitro, C3-8 cycloalkyl, -OR31, -S(0)r2R31, -C(G)OR31, -C(0)R32, -N(R34)R33, -Si(R32a)(R32b)R32c, phenyl, phenyl substituted with (Z2)q2, DM, Dl-32, Dl-33, or Dl-34, or when two R5s are substituents on a same carbon, the two RDs optionally form oxo, thioxo, imino, Ci_6 alkylimino, Ci-e alkoxyimino, or Ci_6 alkylidene,

4 together with each other;
R6 is a hydrogen atom, Ci-6 alkyl, (Ci^) alkyl arbitrarily substituted with R15, C3-8 cycloalkyl, (C3-8) cycloalkyl arbitrarily substituted with R15, C2-6 alkenyl, (C2-6) alkenyl arbitrarily substituted with R15, C3-8 cycloalkenyl, (C3-8) cycloalkenyl arbitrarily 5 substituted with R15, C2-6 alkynyl, (C2-6) alkynyl arbitrarily substituted with R15,
-C(=NOR16)R17, phenyl, phenyl substituted with (Z1)^, Dl-32, Dl-33, Dl-349 Dl-36, Dl-37,orDl-38;
R is a hydrogen atom, C].g alkyl, (Ci-e) alkyl arbitrarily substituted with R , C3-8 cycloalkyl, (C3-8) cycloalkyl arbitrarily substituted with R15b, C2-6 alkenyl, (C2.6) alkenyl 10 arbitrarily substituted with R15b, C3-8 cycloalkenyl, (C3_8) cycloalkenyl arbitrarily
substituted with Ri5b, C2-6 alkynyl, (C2-6) alkynyl arbitrarily substituted withRi5b, phenyl, or phenyl substituted with (Z )qi;
R8a, R8b, R9a, and R9b are each independently a hydrogen atom, cyano, nitro, Ci-6 alkyl, halo (C,.6) alkyl, -OR16a, -S(0)nR16a, -C(0)OR16a, -C(0)R17a, -C(0)N(R19a)R18a, 15 -C(=NORl6a)R17a, phenyl, or phenyl substituted with (Z%;
Ri0, R1! and R12 are each independently a hydrogen atom or C1-6 alkyl;
R15 is a halogen atom, cyano, C3-8 cycloalkyl, -OR16, -S(0)riR16, phenyl, phenyl substituted with (Z\u Di-7, Dl-11, Dl-22, Dl-32, Dl-33, or Dl-34;
R15b is a halogen atom, cyano, C3-8 cycloalkyl, halo (C3-8) cycloalkyl, -OR,6b, 20 -S(0)riR16b, -C(0)ORi6b, ~C(0)N(R18b)R19b, -C(-NOR16b)R17b, -N(R18b)R!9b,
~Si(R32a)(R32b)R32c, phenyl, phenyl substituted with (Z!)qi, Dl-32, Dl-33, Dl-34, Dl-36,
Dl-37, Dl-38, Dl-81, or Dl-84, or when two R15 s are substituents on a same carbon, the
two R15bs optionally form oxo, thioxo, imino, C^ alkylimino, C1-6 alkoxyimino, or C1.6
alkylidene, together with each other;
25 R16, R16a, R16b, R17, R17a, RI7\ R18a, and R!9a are each independently a hydrogen
atom or C1-6 alkyl;
R18b and R19 are each independently a hydrogen atom, C1-6 alkyl, or (Ci.fi) alkyl
9H 1 Sli
arbitrarily substituted with R , or R optionally forms a 3- to 8-membered ring together with a nitrogen atom to which R and R19b are bonded by forming a C2-7 alkylene chain

5 or a C2-7 alkenylene chain together with R , 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 is phenyl or phenyl substituted with (Z )qi;
5 Dl~l to Dl-42, Dl-81, and Dl-84 each are a ring of the following structure;

Xlu (X1)^

o

o

g2

Kj

t1).

Dl-ll

Dl-12

Dl-13

w
^ N

hi

N

ei
(X1),

-:N
N ^
N
Dl-22

N x Dl-21

N-N
Dl-23

>gi

Dl-24

(X\i

-?>

(X'v

N

-N. -N

(X\,
■ N. ,.N


N-N
N

Dl-30



*TW^"'P
7 I

'f'N^

^.,

J A
>g3

5 13

JL7

£„■/

>&

X1 is a halogen atom, cyano, nitro, Ci-6 alkyl, halo (Cm) alkyl, or C3_8 cycloalkyl,

7 when g2, g3, or g4 is an integer of 2 or larger, each X1 is the same as or different from
each other, and further when two Xls are adjacent, the two adjacent X s optionally form a
6-membered ring together with carbon atoms to which each X is bonded by forming
-CH=CHCH=CH-, and at this time, the hydrogen atom bonded to each carbon atom
5 forming the ring is optionally substituted with a halogen atom, cyano, nitro, Ci-6 alkyl,
halo (Ci-6) alkyl, Ci_6 alkoxy, Ci_6 alkylthio, C\^ alkylsulfinyl, or Ci-6 alkylsulfonyl;
Xla is a hydrogen atom or Ci-6 alkyl;
Xlb is Ci_6 alkyl;
Z is a halogen atom, cyano, nitro, Ci-6 alkyl, (Ci^) alkyl arbitrarily substituted with 10 R45, C3.8 cycloalkyl, (C3.8) cycloalkyl arbitrarily substituted with R *, C2-6 alkenyl, (C2-6) alkenyl arbitrarily substituted with R 5, C3-8 cycloalkenyl, (C3-8) cycloalkenyl arbitrarily substituted with R45, C2-6 alkynyl, (C2-6) alkynyl arbitrarily substituted with R 5, -OR , -S(0)r3R41, -C(0)OR41, -C(0)R42, -C(-NOR41)R42, -NCR44)!*43, phenyl, phenyl substituted with (Z3)q3, DM, Dl-2, Dl-7, Dl-10, Dl-11, Dl-22, Dl-32, Dl-33, Dl-34, 15 Dl-36, Dl-37, or Dl-38, and when q is an integer of 2 or larger, each Z is the same as or different from each other;
7} is a halogen atom, cyano, nitro, Ci-6 alkyl, halo (Ci-e) alkyl, Ci-6 alkoxy, or Ci-6
alkoxycarbonyl, and when ql is an integer of 2 or larger, each Z1 is the same as or
different from each other;
20 7} is a halogen atom, cyano, nitro, d-e alkyl, halo (d-6) alkyl, -OR51, -S(0)r2R51,
-C(0)OR51a, -C(0)R529 -C(0)N(R54)R53, -C(S)N(R54)R53, or -N(R54)R53, when q2 is an integer of 2 or larger, each Z is the same as or different from each other, and further when two Z s are adjacent, the two adjacent Z s optionally form a 6-membered ring together with carbon atoms to which each Z is bonded by forming -N=CHCH=CH-,
25 -CH-NCH-CH-, -N=NCH=CH-, -CH-NN-CH-, -N=(
at this time, the hydrogen atom bonded to each carbon atom forming the ring is optionally substituted with a halogen atom, cyano, nitro, Ci-6 alkyl, halo (Ci-6) alkyl, Ci„6 alkoxy, Ci_6 alkylthio, Ci-e alkylsulfinyl, or Ci_6 alkylsulfonyl;
7: is a halogen atom, cyano, nitro, Cj-e alkyl, halo (Ci-6) alkyl, Ci^ alkoxy, halo

(Ci-6) alkoxy, Ci-6 alkylthio, Ci„6 alkylsulfmyl, or Ci-e alkylsulfonyl, and when q3 is an integer of 2 or larger, each Z is the same as or different from each other;
R31 is a hydrogen atom, Ci-e alkyl, (Ci_6) alkyl arbitrarily substituted with R35, -C(0)R37, phenyl, phenyl substituted with (Z2)q2, naphthyl, or naphthyl substituted with 5 (Z2)q2;
R is a hydrogen atom, Cj-6 alkyl, or (C\.e) alkyl arbitrarily substituted with R ;
R32a, R32b, and R32c are each independently Ci.6 alkyl;
R33 and R34 are each independently a hydrogen atom, Ci_6 alkyl, -C(0)OR36, or
-C(0)R37;
10 R35 is a halogen atom, Ci_6 alkoxy, Ci_e alkylthio, Ci-6 alkylsulfmyl, Ci_6
alkylsulfonyl, or phenyl;
R36 is Ci.6 alkyl;
R is a hydrogen atom, Ci-6 alkyl, phenyl, or phenyl substituted with (Z )q2,
R41 is a hydrogen atom, Ci-6 alkyl, (Ci-6) alkyl arbitrarily substituted with R45, 15 phenyl, phenyl substituted with (Z3)q3, Dl-32, Dl-33, or Dl-34;
R4 is a hydrogen atom or Ci-6 alkyl;
R43 and R are each independently a hydrogen atom, Ci_6 alkyl, Ci-6 alkoxycarbonyl, or Ci„6 alkylcarbonyl;
R45 is a halogen atom, C3.8 cycloalkyl, -OH, Ci-6 alkoxy, CMO alkoxycarbonyl, 20 -Si(R32a)(R32b)R32c, phenyl, phenyl substituted with (Z3)q3, Dl-32, Dl-33, or Dl-34, or when two R s are substituents on a same carbon, the two R45s optionally form oxo, thioxo, imino, Ci-6 alkylimino, Ci-e alkoxyimino, or Cj-6 alkylidene, together with each other;
R" is a hydrogen atom, Ci-6 alkyl, halo (Ci-e) alkyl, phenyl, phenyl arbitrarily 25 substituted with a halogen atom, or Dl-39;
R51a and R52 are each independently a hydrogen atom or Ci-6 alkyl;
R5 and R 4 are each independently a hydrogen atom, Ci-e alkyl, or Ci-6
is an integer of 0, 1, 2, 3, 4, or 5;

17 is an integer of 0, 1, 2, 3, 4, 5, 6, or 7; gl and p are each independently an integer of 0 or 1; g2, m, n, rl, 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, ql, q2, and q3 are each independently an integer of 1, 2, 3, 4, or 5]. [0008] [2]
The ketone or oxime compound or a salt thereof according to [1], in which B is a ring of either B-l-a or B-2-a; and

10
15

Za, Zc and Ze are each independently a hydrogen atom, a halogen atom, cyano, nitro, Ci-6 alkyl, (Ci-6) alkyl arbitrarily substituted with R45, C3-8 cycloalkyl, (C3-8) cycloalkyl arbitrarily substituted with R45, C2-6 alkenyl, (C2-6) alkenyl arbitrarily substituted with R45, C2-6 alkynyl, (C2-6) alkynyl arbitrarily substituted with R45, -OR41, -S(0)r3R41, -C(0)OR41, -C(0)R42, -C (=NOR41)R42, -NCR^R43, phenyl, phenyl substituted with (Z3)q3, Dl-l, Dl-2, Dl-7, Dl-10, Dl-11, Dl-22, Dl-32, Dl-33, Dl-34, Dl-36, Dl-37, or Dl-38.
[0009] [3]
The ketone compound or the salt thereof according to [2], in which Q is an oxygen

The oxime compound or a salt thereof according to [2], in which Q is =NOR
The ketone compound or the salt thereof according to [3], in which A is a hydi
.2
atom, Ci_6 alkyl, or -

10 R2 is Ci-8 alkyl;
R6 is Ci-6 alkyl, (Ci-6) alkyl arbitrarily substituted with R15, C3-8 cycloalkyl, C2~6
alkenyl, -C(=NOR16)R17, phenyl, phenyl substituted with (Z1)^, or Dl-32;
R8a is a hydrogen atom, CU6 alkyl, -C(0)OR16a, or -C(0)R!7a;
5 R a is a hydrogen atom or Ci-e alkyl;
R and R are hydrogen atoms;
R10, R11, and R12 are hydrogen atoms;
R15 is a halogen atom, C3-8 cycloalkyl, -OR , or phenyl;
R]6, R16a, R17, and R17a are each independently Ci_6 alkyl;
10 X1 is halo (CU6) alkyl;
Za, Zc and Ze are each independently a hydrogen atom, a halogen atom, Ci-6 alkyl,
C3-8 cycloalkyl, C2-6 alkenyl, (C2-6) alkenyl arbitrarily substituted with R , C2-6 alkynyl,
-OR41, phenyl, phenyl substituted with (Z3)q3, Dl-7, Dl-11, Dl-22, Dl-32, or Dl-37;
Z is a halogen atom;
15 Z is a halogen atom, Ci-g alkyl, halo (Ci-e) alkyl, Ci-6 alkoxy, halo (Ci^) alkoxy, or
Ci-6 alkylthio;
R is Ci-6 alkyl, (Ci-6) alkyl arbitrarily substituted with R45, phenyl, Dl-32, or
Dl-34;
R is a halogen atom, phenyl, or Dl-34;
20 g2, g3, and p are 0;
ql and q3 are integers of 1; and
g4, m, and n are each independently an integer of 0 or 1.
[0012] [6]
The ketone compound or the salt thereof according to [5], in which B is B-l-a;
25 Za is a halogen atom, C^ alkyl, or Ci-6 alkoxy;
Zc is a halogen atom, Cu6 alkyl, €3^ cycloalkyl, C2-6 alkenyl, (C2-6) alkenyl
arbitrarily substituted with R45, C2-6 alkynyl, -OR41, phenyl, phenyl substituted with (Z3)q3,
Dl-7, Dl-11, Dl-22, Dl-32, or Dl-37; and
Ze is a halogen atom or Ci-6 alkyl.

11
[0013] [7]
The oxime compound or the salt thereof according to [4], in which A is a hydrogen atom, Ci-6 alkyl, (C^) alkyl arbitrarily substituted with R5, C3-8 cycloalkyl, C2-6 alkenyl, (C2-6) alkenyl arbitrarily substituted with R5, C2-6 alkynyl, (C2-6) alkynyl arbitrarily 5 substituted with R5, -SCO^R1, -C^OR1, -C(0)SR1, ~C(S)OR1, -C(0)R2, -C(0)N(R4)R3, -C(S)N(R4)R3, or -S(0)2N(R4)R3;
R1 is Ci-8 alkyl, (Ci-e) alkyl arbitrarily substituted with R5, C3.g cycloalkyl, C2~6 alkenyl, phenyl, or phenyl substituted with (Z )q2,
R is C1-8 alkyl, (Cj^) alkyl arbitrarily substituted with R , C^^ cycloalkyl, (C3-8) 10 cycloalkyl arbitrarily substituted with R5, C2-6 alkenyl, (C2-6) alkenyl arbitrarily
substituted with R5, C3-8 cycloaUcenyl, (C3.8) cycloalkenyl arbitrarily substituted with R5, C2-6 alkynyl, (C2-6) alkynyl arbitrarily substituted with R5, -C(=NOR31)R32, phenyl, phenyl substituted with (Z2)q2, Dl-5, Dl-6, Dl-8, Dl-10, or Dl-81;
R is C1-6 alkyl, (Ci^) alkyl arbitrarily substituted with R , C2-6 alkenyl, phenyl, or 15 phenyl substituted with (Z )q2, or R forms a 5- to 6-membered ring together with a nitrogen atom to which R and R are bonded by forming a C4 or C5 alkylene chain together with R , and at this time, the alkylene chain optionally contains one oxygen atom or nitrogen atom and is optionally substituted with Ci-s alkyl;
R is C1-6 alkyl, C2-6 alkenyl, or phenyl;
20 R5 is ahalogen atom, cyano, C3-8 cycloalkyl, -OR31, -S(0)r2R3!, -C(0)OR31,
-C(0)R32, -N(R34)R33, -Si(R32a)(R32b)R32c, phenyl, phenyl substituted with (Z2)q2, or Dl-l, or when two R5s are substituents on a same carbon, the two R s optionally form C1-6 alkoxyimino together with each other;
R is a hydrogen atom, C1-6 alkyl, (C1-6) alkyl arbitrarily substituted with R15, €3.8 25 cycloalkyl, C2~6 alkenyl, -C(-NOR16)R17, phenyl, phenyl substituted with (Z1)^ or, Dl-32;
R is a hydrogen atom, C1-7 alkyl, (Ci-6) alkyl arbitrarily substituted with R , C3-8 cycloalkyl, C2-6 alkenyl, C3-8 cycloalkenyl, (C2-6) alkenyl arbitrarily substituted with R15 , C2-6 alkynyl, or phenyl;

12 R8a is a hydrogen atom, Cue alkyl, halo (Ci-6) alkyl, -C(0)OR!6a, -C(=NOR16a)R17a,
or phenyl substituted with (Z )qi;
R9a is a hydrogen atom or Ci-6 alkyl;
R8b and R9b are hydrogen atoms;
5 R is a hydrogen atom;
R15 is a halogen atom, C3.8 cycioalkyl, or -OR ;
R15b is a halogen atom, cyano, C3.8 cycioalkyl, halo (C3-8) cycioalkyl, -OR16b,
-S(0)nR16b5 -C(0)OR16b, -C(0)N(R18b)R19b, -C(-NOR16b)R,7b, -N(Rl8b)Ri9b,
-Si(R32a)(R32b)R32c, phenyl, phenyl substituted with (Z1)^, Dl-32, or Dl -84;
10 R16, R16a, R17, R17a, and R17b are each independently C w alkyl;
R18b is a hydrogen atom, Ci-6 alkyl, or (Ci-e) alkyl arbitrarily substituted with R20, or
R38b forms a 6-membered ring together with a nitrogen atom to which R18b and R19b are
bonded by forming a C5 alkylene chain together with R19b, and at this time, the alkylene
chain contains one oxygen atom;
15 R19b is a hydrogen atom or Ci-6 alkyl;
R20 is phenyl substituted with (Z^qi;
X1 is a halogen atom, Ci-e alkyl, halo (Cue) alkyl, or C3.8 cycioalkyl, g3 is an integer
of 2, and further the two adjacent Xls form a 6-membered ring together with carbon
atoms to which each X1 is bonded by forming -CH=CHCH=CH-, and at this time, one
20 hydrogen atom bonded to each carbon atom forming the ring is arbitrarily substituted
with a halogen atom;
Xla is C,_6 alkyl;
Za, Zc, and Ze are each independently a hydrogen atom, a halogen atom, cyano, nitro,
Ci„6 alkyi, C3.8 cycioalkyl, C2-6 alkenyl, (C2-6) alkenyl arbitrarily substituted with R45, C2-6
25 alkynyl, (C2-6) alkynyl arbitrarily substituted with R45, -OR41, -S(0)r3R41, -C(0)OR41,
-C(0)R42, -C(=NOR41)R42, -N(R44)R43, phenyl, phenyl substituted with (Z3)q3, Dl-2,
Dl-7, Dl -11, Dl-22, Dl-32, Dl-33, Dl-34, or Dl-37,
l} is a halogen atom, nitro, Ci_6 alkyl, halo (Ci-e) alkyl, Ci-6 alkoxy, or Ci-6
alkoxycarbonyl, and when ql is an integer of 2 or larger, each Z is the same as or

13 different from each other;
Z is a halogen atom, cyano, nitro, Ci-6 alkyl, halo (C^) alkyl, -OR51, -S(0)r2R5 , -C(0)OR5,a, -C(0)R52, or -C(0)N(R54)R53, when q2 is an integer of 2 or larger, each Z2 is the same as or different from each other, and further when the two Z s are adjacent, the 5 two adjacent Z2s optionally form a 6-membered ring together with carbon atoms to which each Z 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;
Z3 is a halogen atom, Ci_6 alkyl, halo (Ci-e) alkyl, Cu6 alkoxy, halo (Ci-e) alkoxy, or 10 Ci-6 alkylthio, and when q3 is an integer of 2 or larger, each Z is the same as or different from each other;
R31 is Ci-e alkyl, (Ci-e) alkyl arbitrarily substituted with R35, -C(0)R37, phenyl, phenyl substituted with (Z )q2, or naphthyl;
R32 is Ci-6 alkyl or (Ci_6) alkyl arbitrarily substituted with R35;
15 R33 is-C(0)R37;
R34 is Ci_6 alkyl;
R" is a halogen atom, Ci-6 alkylthio, or phenyl;
R is Ci_6 alkyl or phenyl;
R41 is a hydrogen atom, Ci-6 alkyl, (Ci^) alkyl arbitrarily substituted with R45, 20 phenyl, or Dl-32;
R42 is CU6 alkyl;
R43 is Ci„6 alkoxycarbonyl;
R44 is a hydrogen atom;
R45 is a halogen atom, C3.8 cycloalkyl, -OH, Ci-6 alkoxy, CMO alkoxycarbonyl, 25 -Si(R32a)(R32h)R32c, phenyl, or Dl-34;
R51 is C).6 alkyl, halo (Ci-e) alkyl, phenyl arbitrarily substituted with a halogen atom,
L51aisCi.6
R and R are each independently C1.6 alkyl;

14 g2 is an integer of 0, 1, or 2;
g3 and rl are each independently an integer of 0, 1, or 2;
g4, m, and n are each independently an integer of 0 or 1;
17, p, andr3 are 0;
5 q is an integer of 2 or 3;
ql 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.
10 [0014] [8]
The oxime compound or the salt according to [7], in which B is B-l-a;
Za is a halogen atom, Ci_6 alkyl, Ci_6 alkoxy, or Ci_6 alkylthio;
Zc is a hydrogen atom, a halogen atom, cyano, nitro, Ci-6 alkyl, C3-8 cycloalkyl, C2-6 alkenyl, (C2-6) alkenyl arbitrarily substituted with R45, C2-6 alkynyl, (C2-6) alkynyl 15 arbitrarily substituted with R45, -OR41, -S(0)r3R41, -C(0)OR41, -C(0)R42, -C(=NOR41)R42, -N(R44)R43, phenyl, phenyl substituted with (Z3)q3, Dl-2, Dl-7, Dl-11, Dl-22, Dl-32, Di-33,Dl-34,orDl-37;
Ze is a halogen atom, Ci-6 alkyl, or C1-6 alkoxy;
X1 is a halogen atom or halo (Ci_6) alkyl; and
20 g3 is an integer of 0 or 1.
[0015] [9]
The ketone or oxime compound or the salt thereof according to [1], in which B is B-l or B-2.
[0016] [10]
25 The ketone or oxime compound or the salt thereof according to [1 ], in which B is
B-l.
[0017] [11]
The ketone or oxime compound or the salt thereof according to [1], in which B is B-2.

15 [0018] [12]
The ketone or oxime compound or the salt thereof according to [1], in which B is
*-3.
[0019] [13]
5 The ketone or oxime compound or the salt thereof according to [2], in which B is
B-1-a.
[0020] [14]
The ketone or oxime compound or the salt thereof according to [2], in which B is
B-l-b.
10 [0021] [15]
The ketone compound or the salt tliereof according to [3], in which B is B-1 or B-2.
[0022] [16]
The ketone compound or the salt thereof according to [3], in which B is B-1.
[0023] [17]
15 The ketone compound or the salt tliereof according to [3], in which B is B-2.
[0024] [18]
The ketone compound or the salt thereof according to [3], in which B is B-3.
[0025] [19]
The ketone compound or the salt thereof according to [3] and [5], in which B is
20 B-1-;
[0026] [20]
The ketone compound or the salt thereof according to [3] and [5], in which B is
25 The oxime compound or the salt thereof according to [4], in which B is B-1 or B-2.
The oxime compound or the salt thereof according to [4], in which B is B-1.
[0029] [23]
The oxime compound or the salt thereof according to [4], in which B is B-2.

16 [0030] [24]
The oxime compound or the salt thereof according to [4], in which B is B-3.
[0031] [25]
The oxime compound or the salt thereof according to [4] and [7], in which B is 5 B-l-a.
[0032] [26]
The oxime compound or the salt thereof according to [4] and [7], in which B is B-l-b.
[0033] [27]
10 The ketone or oxime compound or the salt thereof according to [1] to [26], in which
A is a hydrogen atom, Ci_6 alkyl, (Ci-6) alkyl arbitrarily substituted with R5, C3.8 cycloalkyl, C2-6 alkenyl, (C2-6) alkenyl arbitrarily substituted with R5, C2-6 alkynyl, or (C2-6) alkynyl arbitrarily substituted with R5.
[0034] [28]
15 The ketone or oxime compound or the salt thereof according to [1] to [26], in which
A is a hydrogen atom, Ci_6 alkyl, (Ci-s) alkyl arbitrarily substituted with R5, C2-6 alkenyl, C2-6 alkynyl, or (C2-6) alkynyl arbitrarily substituted with R5.
[0035] [29]
The ketone or oxime compound or the salt thereof according to [1] to [26], in which 20 A is a hydrogen atom, Ci_6 alkyl, or (C1-6) alkyl arbitrarily substituted with R5.
[0036] [30]
The ketone or oxime compound or the salt thereof according to [1] to [26], in which
A is a hydrogen atom, -S(0)r2R\ -0(0)0^, -C(0)SR\ -QSpR1, -C(0)R2,
-C(0)N(R4)R3, -C(S)N(R4)R3, or -S(G)2N(R4)R3.
25 [0037] [31]
The ketone or oxime compound or the salt thereof according to [1] to [26], in which A is a hydrogen atom, -C(0)OR!, -C(0)SR1, -C(0)R2, -C(0)N(R4)R3, or -C(S)N(R4)R3.
[0038] [32]
The ketone or oxime compound or the salt thereof according to [1] to [26], in which

17 A is a hydrogen atom, -C(0)SR1, -C(0)R2, or -C(0)N(R4)R3.
[0039] [33]
The ketone or oxime compound or the salt thereof according to [ 1 ] to [26], in which
A is a hydrogen atom.
5 [0040] [34]
The ketone or oxime compound or the salt thereof according to [1] to [26], in wliich
A is C i-6 alkyl or (Ci^) alkyl arbitrarily substituted with R5.
[0041] [35]
The ketone or oxime compound or the salt thereof according to [1] to [26], in which
10 A is C2-6 alkynyl or (C2-6) alkynyl arbitrarily substituted with R5.
[0042] [36]
The ketone or oxime compound or the salt thereof according to [ 1 ] to [26], in which
Ais-C(0)SR[0043] [37]
15 The ketone or oxime compound or the salt thereof accordmg to [1] to [26], in which
Aisa-C(0)R2.
[0044] [38]
The ketone or oxime compound or the salt thereof accordmg to [1] to [26], in which
Ais-C(0)N(R4)R3.
20 [0045] [39]
The ketone or oxime compound or the salt thereof accordmg to [1] to [26], in which
The ketone or oxime compound or the salt thereof according to [1] to [39], in which 25 R1 is Cus alkyl, (Ci_6) alkyl arbitrarily substituted with R5, C3-8 cycloalkyl, or C2-6
The ketone or oxime compound or the salt thereof according to [1] to [39], in which R1 is C1.8 alkyl.

18 [0048] [42]
The ketone or oxime compound or the salt thereof according to [1] to [39], in which R1 is (Ci-6) allcyl arbitrarily substituted with R5.
[0049] [43]
5 The ketone or oxime compound or the salt thereof according to [1] to [39], in which
R is C3„8 cycloalkyl.
[0050] [44]
The ketone or oxime compound or the salt thereof according to [1] to [39], in which
R1 is C2-6 alkenyl.
10 [0051] [45]
The ketone or oxime compound or the salt thereof according to [1] to [44], in which R is C1-8 alkyl, (Ci^) alkyl arbitrarily substituted with R , C3-8 cycloalkyl, (C3^) cycloalkyl arbitrarily substituted with R5, C2-6 alkenyl, (C2-6) alkenyl arbitrarily substituted with R5, C3.8 cycloalkenyl, (C3-8) cycloalkenyl arbitrarily substituted with R5, 15 C2-6 alkynyl, (C2-6) alkynyl arbitrarily substituted with R5, or -C(=NOR31)R32.
[0052] [46]
The ketone or oxime compound or the salt thereof according to [ 1 ] to [44], in which R2 is C1-8 alkyl or (Ci_6) alkyl arbitrarily substituted with R5.
[0053] [47]
20 The ketone or oxime compound or the salt thereof according to [1] to [44], in which
R2 is C3-8 cycloalkyl or (C3-8) cycloalkyl arbitrarily substituted with R[0054] [48]
The ketone or oxime compound or the salt thereof according to [1] to [44], in which
R is C2-6 alkenyl or (C2-6) alkenyl arbitrarily substituted with R .
25 [0055] [49]
The ketone or oxime compound or the salt thereof according to [1] to [44], in which R is C3-8 cycloalkenyl or (C3-8) cycloalkenyl arbitrarily substituted with R .
[0056] [50]
The ketone or oxime compound or the salt thereof according to [1] to [44], in which

19 R is C2-6 alkynyl or (C2-6) alkynyl arbitrarily substituted with R .
[0057] [51]
The ketone or oxime compound or the salt thereof according to [1] to [44], in which
R2 is phenyl, phenyl substituted with (Z2)q2, Dl-5, Dl-6, Dl-8, Dl-10, or Dl-81.
5 [0058] [52]
The ketone or oxime compound or the salt thereof according to [1] to [44], in which R2 is C1-8 alkyl.
[0059] [53]
The ketone or oxime compound or the salt thereof according to [1] to [44], in which 10 R2 is (C1.6) alkyl arbitrarily substituted with R5.
[0060] [54]
The ketone or oxime compound or the salt thereof according to [1] to [53], in which
R is C1-6 alkyl, (Ci^) alkyl arbitrarily substituted with R , C2-6 alkenyl, phenyl, or phenyl
substituted with (Z )q2.
15 [0061] [55]
The ketone or oxime compound or the salt thereof according to [1] to [53], in which R is C1-6 alkyl, (C1-6) alkyl arbitrarily substituted with R , or C2-6 alkenyl,
[0062] [56]
The ketone or oxime compound or the salt thereof according to [1] to [53], in which 20 R3 is phenyl or phenyl substituted with (Z2)q2.
[0063] [57]
The ketone or oxime compound or the salt thereof according to [1] to [53], in which R3 forms a 5- or 6-membefed ring together with a nitrogen atom to which R~ and R4 are bonded by forming a C4 or C5 alkylene chain together with R , and at this time, the 25 alkylene chain optionally contains one oxygen atom or nitrogen atom and is optionally substituted with C1-6 alkyl.
[0064] [58]
The ketone or oxime compound or the salt thereof according to [1] to [57], in which R5 is a halogen atom, cyano, C3-8 cycloalkyl, -OR31, -S(0)r2R31, -C(0)OR31, phenyl, or

20 phenyl substituted with (Z )q2.
[0065] [59]
The ketone or oxime compound or the salt thereof according to [1] to [57], in which
R5 is a halogen atom, -OR31, or -S(0)r2R31.
5 [0066] [60]
The ketone or oxime compound or the salt thereof according to [1] to [57], in which R5 is a halogen atom.
[0067] [61]
The ketone or oxime compound or the salt thereof according to [1] to [57], in which 10 R5is-OR31.
[0068] [62]
The ketone or oxime compound or the salt thereof according to [1] to [57], in which R5is-S(0)r2R31.
[0069] [63]
15 The ketone or oxime compound or the salt thereof according to [ 1 ] to [5 7], in which,
when two R5s are substituents on a same carbon, the two R5s optionally form Ci-6 alkoxyimino together with each other.
[0070] [64]
The ketone or oxime compound or the salt thereof according to [1] to [63], in which 20 R6 is Ci_6 alkyl, (Ci„6) alkyl arbitrarily substituted with R15, C3-s cycloalkyl, or C2-6 alkenyl.
[0071] [65]
The ketone or oxime compound or the salt thereof according to [1] to [63], in which
R6 is phenyl, phenyl substituted with (Zl)q\, or Dl-32.
25 [0072] [66]
The ketone or oxime compound or the salt thereof according to [1] to [63], in which R6 is Ci-6 alkyl or C3.8 cycloalkyl.
[0073] [67]
The ketone or oxime compound or the salt thereof according to [1] to [63], in which

21 R6 is d_6 alkyl.
[0074] [68]
The ketone or oxime compound or the salt thereof according to [1] to [63], in which
R6 is C3.8 cycloalkyl.
5 [0075] [69]
The oxime compound or the salt thereof according to [1], [2], [4], [7] to [14], and
[21] to [63], in which R' is a hydrogen atom, Cj-7 alkyl, (C1-6) alkyl arbitrarily substituted
with R 5b, C3-8 cycloalkyl, C2.6 alkenyl, C3-8 cycloalkenyl, (C2-6) alkenyl arbitrarily
substituted with R15 , or C2-6 alkynyl.
10 [0076] [70]
The oxime compound or the salt thereof according to [1], [2], [4], [7] to [14], and [21] to [63], in which R is a hydrogen atom, C1-7 alkyl, or (C1-6) alkyl arbitrarily substituted with Ri5b.
[0077] [71]
15 The oxime compound or the salt thereof according to [1], [2], [4], [7] to [14], and
[21] to [63], in which R is a hydrogen atom.
[0078] [72]
The oxime compound or the salt thereof according to [1], [2], [4], [7] to [14], and
[21] to [63], in which R7 is C1.7 alkyl.
20 [0079] [73]
The oxime compound or the salt thereof according to [1], [2], [4], [7] to [14], and [21] to [63], in which R7 is (Ci_6) alkyl arbitrarily substituted with R15b.
[0080] [74]
The ketone or oxime compound or the salt thereof according to [1] to [73], in which 25 R8a is a hydrogen atom, Ci-e alkyl, halo (d.6) alkyl, or -C(0)OR!6a.
[0081] [75]
The ketone or oxime compound or the salt thereof according to [1] to [73], in which R a is a hydrogen atom or C^6 alkyl.
[0082] [76]

22 The ketone or oxime compound or the salt thereof according to [1] to [73], in which
R8a is a hydrogen atom.
[0083] [77]
The ketone or oxime compound or the salt thereof accordmg to [1] to [73], in which
5 R8a is Ci-6 alkyl.
[0084] [78]
The ketone or oxime compound or the salt thereof according to [1] to [77], in which
R9a is a hydrogen atom.
[0085] [79]
10 The ketone or oxime compound or the salt thereof according to [1] to [79], in which
R9a is Ci_6 alkyl.
[0086] [80]
The ketone or oxime compound or the salt thereof according to [1] to [79], in which
R 5 is a halogen atom.
15 [0087] [81]
The ketone or oxime compound or the salt thereof according to [1] to [79], in which
R15 is C3_8 cycloalkyl.
[0088] [82]
The ketone or oxime compound or the salt thereof according to [1] to [79], in which
20 R15 is -OR16.
[0089] [83]
The oxime compound or the salt thereof according to [1], [2], [4], [7] to [14], and
[21 ] to [82], in which R15b is a halogen atom, cyano, halo (C3-8) cycloalkyl, -GR16b,
-S(0)nR16b, or -C(0)N(R18b)Ri9b„
25 [0090] [84]
The oxime compound or the salt thereof according to [1], [2], [4], [7] to [14], and
[21] to [82], in which R15b is a halogen atom, cyano, -OR16b, or -S(G)riR16b.
[0091] [85]
The oxime compound or the salt thereof according to [1], [2], [4], [7] to [14], and

23 [23]to [82], in which R15 is a halogen atom.
[0092] [86]
The oxime compound or the salt thereof according to [1], [2], [4], [7] to [14], and
[21] to [82], in which R15b is cyano.
5 [0093] [87]
The oxhne compound or the salt thereof according to [1], [2], [4], [7] to [14], and [21] to [82], in which R15b is -ORi6b.
[0094] [88]
The oxime compound or the salt thereof according to [1], [2], [4], [7] to [14], and 10 [21] to [82], in which R15b is -S(0)rlR16b.
[0095] [S9]
The oxime compound or the salt thereof according to [1], [2], [4], [7] to [14], and [21] to [82], in which R15b is phenyl, phenyl substituted with (Z1)^, Dl-32, or Dl-84.
[0096] [90]
15 The oxime compound or the salt thereof according to [1], [2], [4], [7] to [14], and
[21] to [82], in which R,5b is phenyl or phenyl substituted with (Z1^.
[0097] [91]
The oxime compound or the salt thereof according to [1], [2], [4], [7] to [14], and
[21] to [90], in which R18b is a hydrogen atom or Ci_6 alkyl.
20 [0098] [92]
The oxime compound or the salt thereof according to [1], [2], [4], [7] to [14], and
[21] to [90], in which R b forms a 6-membered ring together with a nitrogen atom to
which R 8b and R19 are bonded by forming a C5 alkylene chain together with R! b, and at
this time, the alkylene chain contains one oxygen atom.
25 [0099] [93]
The ketone or oxime compound or the salt thereof according to [1] to [92], in which X1 is halo (C1-6) alkyl or C3-8 cycloalkyl.
[0100] [94]
The ketone or oxime compound or the salt thereof according to [1] to [92], in which

24 X1 is a halogen atom or Ci-6 alkyl.
[0101] [95]
The ketone or oxhne compound or the salt thereof according to [1] to [92], in which
X1 is a halogen atom.
5 [0102] [96]
The ketone or oxime compound or the salt thereof according to [1] to [92], in which
X1 is Ci-6 alkyl.
[0103] [97]
The ketone or oxime compound or the salt thereof according to [1] to [96], in which
10 Za is a halogen atom.
[0104] [98]
The ketone or oxime compound or the salt thereof according to [1] to [96], in which
Zais Ci-6 alkyl.
[0105] [99]
15 The ketone or oxime compound or the salt thereof according to [1] to [96], in which
Zais Cj-6 alkoxy.
[0106] [100]
The ketone or oxime compound or the salt thereof according to [1] to [96], in which
ZaisCi.6alkylthio.
20 [0107] [101]
The ketone or oxime compound or the salt thereof according to [1] to [100], in
which Zc is a hydrogen atom, a halogen atom, cyano, Ci-e alkyl, C2-6 alkynyl, (C2-6)
alkynyl arbitrarily substituted with R45, phenyl, phenyl substituted with (Z3)q3, Dl-2,
Dl-7, Dl-11, Dl-22, Dl-32, Dl-33, Dl-34, or Dl-37.
25 [0108] [102]
The ketone or oxime compound or the salt thereof according to [1] to [100], in
which Zc is a hydrogen atom, a halogen atom, cyano, Ci-6 alkyl, C2-6 alkynyl, or (C2-6)
alkynyl arbitrarily substituted with R45.
[0109] [103]

25 The ketone or oxime compound or the salt thereof according to [1] to [100], in
which Zc is phenyl, phenyl substituted with (Z3)q3, Dl-2, Dl-7, Dl-11, Dl-22, Dl-32,
Dl-33, Dl-34, or Dl-37.
[0110] [104]
5 The ketone or oxime compound or the salt thereof according to [1] to [100], in
which Zc is Ci_6 alkyl.
[0111] [105]
The ketone or oxime compound or the salt thereof according to [1] to [100], in
which Zc is C2-e alkynyl or (C2-6) alkynyl arbitrarily substituted with R45.
10 [0112] [106]
The ketone or oxime compound or the salt thereof according to [1] to [100], in which Zc is phenyl or phenyl substituted with (Z3)q3.
[0113] [107]
The ketone or oxime compound or the salt thereof according to [1] to [100], in 15 which Zc is Dl-2, Dl-7, Dl-32, Dl-33, Dl-34, or Dl-37.
[0114] [108]
The ketone or oxime compound or the salt thereof according to [1] to [100], in which Zc is Dl-32, Dl-33, or Dl-34.
[0115] [109]
20 The ketone or oxime compound or the salt thereof according to [1] to [100], in
which Zc is Dl-7.
[0116] [110]
The ketone or oxime compound or the salt thereof according to [ 1 ] to [ 109], in
which Ze is a halogen atom.
25 [0117] [111]
The ketone or oxime compound or the salt thereof according to [1] to [] 09], in which Ze is Cj-6 alkyl.
[0118] [112]
The ketone or oxime compound or the salt thereof according to [1] to [109], in

26 which Ze is Ci-6 alkoxy.
[0119] [113]
The ketone or oxime compound or the salt thereof according to [ 1 ] to [ 109], in which Ze is Ci_6 alkylthio.
[0120] [114]
The ketone or oxime compound or the salt thereof according to [1] to [113], in which Z is a halogen atom, cyano, nitro, Ci-6 alkyl, halo (Ci^) alkyl, -OR , or -S(0)r2R51.
[0121] [115]
The ketone or oxime compound or the salt thereof according to [1] to [113], in which Z is a halogen atom, cyano, nitro, Ci-6 alkyl, or halo (Ci^) alkyl.
[0122] [116]
The ketone or oxime compound or the salt thereof according to [1] to [113], in which Z is a halogen atom or Ci-6 alkyl.
[0123] [117]
The ketone or oxime compound or the salt thereof according to [1] to [113], in which Z2 is -OR51 or -S(0)r2R5!.
[0124] [118]
The ketone or oxime compound or the salt thereof according to [1] to [113], in which Z is a halogen atom.
[0125] [119]
The ketone or oxime compound or the salt thereof according to [1] to [113], in which Z is Ci-6 alkyl.
[0126] [120]
The ketone or oxime compound or the salt thereof according to [1] to [113], in which Z2 is-OR51.
[0127] [121]
The ketone or oxime compound or the salt thereof according to [1] to [113], in which Z2 is-S(0)r2R51.

27 [0128] [122]
The ketone or oxime compound or the salt thereof according to [1] to [121], in
which Z3 is a halogen atom or halo (CK,) alkoxy.
[0129] [123]
5 The ketone or oxime compound or the salt thereof according to [1] to [121], in
which Z is a halogen atom.
[0130] [124]
The ketone or oxime compound or the salt thereof according to [ 1 ] to [ 121 ], in
which Z3 is halo (Ci_6) alkoxy.
10 [0131] [125]
The ketone or oxime compound or the salt thereof accordmg to [1] to [124], in
which R32 is Ci-ealkyl.
[0132] [126]
The ketone or oxime compound or the salt thereof according to [1] to [124], in
15 which R32 is (Ci-6) alkyl arbitrarily substituted with R35.
[0133] [127]
The ketone or oxime compound or the salt thereof according to [1 ] to [126], hi
which R35 is a halogen atom.
[0134] [128]
20 The ketone or oxime compound or the salt thereof according to [1] to [126], in
which R35 is Ci-6 alkylthio.
[0135] [129]
The ketone or oxime compound or the salt thereof according to [1] to [126], in
which R ' is phenyl.
25 [0136] [0130]
The ketone or oxime compound or the salt thereof according to [ 1 ] to [ 129], in
which R37 is Ci-6 alkyl.
[0137] [131]
The ketone or oxime compound or the salt thereof according to [1] to [129], in

28 which R is phenyl.
[0138] [132]
The ketone or oxime compound or the salt thereof according to [ 1 ] to [ 131 ], in
which R41 is a hydrogen atom, Ci„6 alkyl, or (Ci^) alkyl arbitrarily substituted with R45.
5 [0139] [133]
The ketone or oxime compound or the salt thereof according to [1] to [131], in which R is phenyl or Dl-32.
[0140] [134]
The ketone or oxime compound or the salt thereof according to [1] to [131], in 10 which R41 is a hydrogen atom.
[0141] [135]
The ketone or oxime compound or the salt thereof according to [1] to [131], in which R41 is Ci .6 alkyl.
[0142] [136]
15 The ketone or oxime compound or the salt thereof according to [1] to [131], in
which R41 is (Ci-e) alkyl arbitrarily substituted with R45.
[0143] [137]
The ketone or oxime compound or the salt thereof according to [1] to [136], in
which R45 is a halogen atom, C3„g cycloalkyl, -OH, or C[-6 alkoxy.
20 [0144] [138]
The ketone or oxime compound or the salt thereof according to [1] to [136], in which R45 is phenyl or Dl-34,
[0145] [139]
The ketone or oxime compound or the salt thereof according to [1] to [136], in 25 which R is a halogen atom.
[0146] [140]
The ketone or oxime compound or the salt thereof according to [1] to [136], in which R45 is C3„8 cycloalkyl.
[0147] [141]

29 The ketone or oxime compound or the salt thereof according to [1] to [136], in
which R45 is -OH.
[0148] [142]
The ketone or oxime compound or the salt thereof according to [1] to [136], in
5 which R45 is Ci-6 alkoxy.
[0149] [143]
The ketone or oxime compound or the salt thereof according to [1] to [142], in
which R51 is Ci-ealkyl.
[0150] [144]
10 The ketone or oxime compound or the salt thereof according to [1] to [143], in
which m is an integer of 0 or 1.
[0151] [145]
The ketone or oxime compound or the salt thereof according to [1] to [143], in
which m is an integer of 0.
15 [0152] [146]
The ketone or oxime compound or the salt thereof according to [1] to [143], in
which m is an integer 6F Y.
[0153] [147]
The ketone or oxime compound or the salt thereof according to [1] to [146], in
20 which n is an integer of 0 or 1.
[0154] [148]
The ketone or oxime compound or the salt thereof according to [1] to [146], in
which n is an integer of 0.
[0155] [149]
25 The ketone or oxime compound or the salt thereof according to [1] to [146], in
which n is an integer of 1.
[0156] [150]
An agricultural chemical comprising one or more of compounds selected from
ketone or oxime compound or the salt thereof according to [1] to [149] as an active

30 component.
[0157] [151]
A herbicide comprising one or more of compounds selected from the ketone or oxime compound or the salt thereof according to [1] to [149] as an active component. 5 Effects of the Invention
[0158] The compound of the present invention has excellent herbicidal activity
against various weeds and has high safety to target crops as well as has almost no adverse
effect on non-target creatures such as mammals, fish, and beneficial insects and has light
environmental burden due to low residual properties.
10 Accordingly, the present invention can provide a useful herbicide in the agricultural
and horticultural fields such as paddy fields, farmlands, and orchards.
MODES FOR CARRYING OUT THE INVENTION
[0159] The compound of Formula (1) of the present invention may exist as, for 15 example, keto-enol structural tautomers of the following formula depending on the kind of the substituent and conditions. The present invention includes all of these structures.

[0160] The compounds included in the present invention may include the
geometric isomers of an E-form having an E-configuration and a Z-form having a 20 Z-configuration depending on the types of the substituents. The present invention
includes the E-form, the Z-form, and a mixture of the E-form and the Z-form in any ratios. In the present specification, these forms are represented as, for example, a bond of wavy lines illustrated below.

31

The compounds included in the present invention include optically active isomers
due to the existence of one or more of asymmetric carbon atoms. The present invention
includes all optically active isomers or racemic forms.
5 [0161] Among the compounds included in the present invention, the compounds
that can form an acid-added salt by a conventional method may form, for example, the salts of hydrohaiic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, and hydroiodic acid; the salts of inorganic acids such as nitric acid, sulfuric acid, phosphoric acid, chloric acid, and perchloric acid; the salts of sulfonic acids such as
10 methanesulfonic acid, ethane sulfonic acid, trifluoromethanesulfonic acid,
benzenesulfonic acid, and p-toluenesulfonic acid; the salts of carboxylic acids such as formic acid, acetic acid, propionic acid, trifhioroacetic acid, fumaric acid, tartaric acid, oxalic acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acid, and citric acid; or the salts of amino acids such as
15 glutamic acid and aspartic acid.
[0162] Among the compounds included in the present invention, the compounds that can form a metal salt by a conventional method may form, for example, the salts of alkali metals such as lithium, sodium, and potassium; the salts of alkaline earth metals such as calcium, barium, and magnesium; or the salt of aluminum.
20 [0163] Subsequently, specific examples of each substituent described in the
present specification will be described below. Here, n- means normal; i- means iso; s-means secondary; and tert- means tertiary; and Ph means phenyl.
[0164] Examples of the halogen atom in the present specification may include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. The expression of
25 "halo" in the present specification is also these halogen atoms.

32 [0165] The expression of Ca.b alkyl in the present specification is a linear chain
or a branched chain hydrocarbon group made of the number of carbon atoms of a to b.
Specific examples of the Ca-b alkyl may include methyl group, ethyl group, n-propyl
group, i-propyl group, n-butyl group, i-butyl group, s-butyl group, tert-butyl group,
5 n-pentyl group, 1,1-dimethylpropyl group, and n-hexyl group and the like. Each of
these groups is selected in a range of the specified number of carbon atoms.
[0166] The expression of Ca-b alkenyl in the present specification is a linear
chain or a branched chain unsaturated hydrocarbon group made of the number of carbon
atoms of a to b and having one or more double bonds in the molecule. Specific
10 examples of the Ca-b alkenyl may include vinyl group, 1-propenyl group, 2-propenyl group, 1-methyl ethenyl group, 2-butenyl group, 2-methyl-2-propenyl group, 3-methyf 2-butenyl group, and l,l-dimethyl-2-propenyl group and the like. Each of these groups is selected in a range of the specified number of carbon atoms.
[0167] The expression of Ca-b alkynyl in the present specification is a linear
15 chain or a branched chain unsaturated hydrocarbon group made of the number of carbon atoms of a to b and having one or more triple bonds in the molecule. Specific examples of the Ca-b alkenyl may include ethynyl group, 1-prbpynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, and l,l-dimethyl-2-propynyl group and the like. Each of these groups is selected in a range of the specified number of
20 carbon atoms.
[0168] The expression of halo (Ca~b) alkyl in the present specification is a linear chain or a branched chain hydrocarbon group made of the number of carbon atoms of a to b in which the hydrogen atoms bonded to the carbon atom are arbitrarily substituted with halogen atoms. When the compound is substituted with two or more halogen atoms,
25 these halogen atoms may be the same as or different from each other. Specific examples of the Ca_b haloalkyl may include fluoromethyl group, chloromethyl group, bromomethyl group, iodomethyl group, difluoromethyl group, dichloromethyl group, trifluoromethyl group, chlorodifluoromethyl group, trichloromethyl group, bromodifluoromethyl group, 2-fluoroethyl group, 2-chloroethyl group, 2-bromoethyl group, 2,2-difluoroethyi group,

33 2,2,2-trifluoroethyl group, 2-chloro-2,2-difluoroethyl group, 2,2,2-trichloroethyl group,
1,1,2,2-tetrafluoroethyl group, 2-chloro-l,l,2-trifluoroethyl group, pentafluoroethyl
group, 3,3,3-triftuoropropyl group, 2,2,3,3,3-pentafluoropropyl group,
1,1,2,3,3,3-hexafluoropropyl group, heptafluoropropyl group, 2,2,2-trifluoro-l-
(trifluoromethyl)ethyl group, l,2,2,2-tetrafluoro-l-(trifluoromethyl)ethyl group,
2,2,3,3,4,4,4-heptafluorobutyl group, and nonafluorobutyl group and the like. Each of
these groups is selected in a range of the specified number of carbon atoms.
[0169] The expression of Ca-b cycloalkyl in the present specification is a cyclic hydrocarbon group made of the number of carbon atoms of a to b and can form a monocyclic structure or a fused ring structure of a 3-membered ring to a 6-membered ring. Each ring is optionally substituted with an allcyl group in a range of the specified number of carbon atoms. Specific example of the Ca-b cycloalkyl may include cyclopropyl group, 1-methylcyclopropyl group, 2-methylcyclopropyl group, 2,2-dimethylcyclopropyl group, cyclobutyl group, cyclopentyl group, and cyclohexyl group and the lilce. Each of these groups is selected in a range of the specified number of carbon atoms.
[0170] The expression of halo (Ca-b) cycloalkyl hrthe present specification is a cyclic hydrocarbon group made of the number of carbon atoms of a to b in which the hydrogen atoms bonded to the carbon atom are arbitrarily substituted with halogen atoms and can form a monocyclic structure or a conjugated-cyclic structure of a 3-membered ring to a 6-membered ring. Each ring can be optionally substituted with an alkyl group in a range of the specified number of carbon atoms. The substitution position with the halogen atom may be at a ring structure part, at a side chain structure part, or at both of them. When the compound is substituted with two or more halogen atoms, these halogen atoms may be the same as or different from each other. Specific examples of the halo (Ca-b) cycloalkyl may include 2,2-difluorocyclopropyl group, 2,2-dichlorocyclopropyl group, 2,2-dibromocyclopropyl group, 2,2~diftuoro- 1-methylcyclopropyl group, 2,2-dichloro-l-methylcyciopropyl group, 2,2-dibromo-l-methylcyclopropyl group, and 2,2,3,3-tetrafluorocyclobutyl group and the

34 like. Each of these groups is selected in a range of the specified number of carbon
atoms,
[0171] The expression of Ca-b cycloalkenyl in the present specification is a
cyclic unsaturated hydrocarbon group made of the number of carbon atoms of a to b and 5 having one or more double bonds and can form a monocyclic structure or a fused ring
structure of a 3-membered ring to a 6-membered ring. Each ring can be optionally
substituted with an alkyl group in a range of the specified number of carbon atoms. The
double bond may be either an endo-form or an exo-form. Specific example of the Ca-b
cycloalkenyl may include 1-cyclopentene-l-yl group, 2-cyclopentene-l-yl group, 10 1 -cyclohexen-1 -yl group, and 2-cyclohexen-1 -yl group and the like. Each of these
groups is selected in a range of the specified number of carbon atoms.
[0172] The expression of Ca_b alkoxy in the present specification is an alkyl-O-
group in which this alkyl is the above meaning alkyl made of the number of carbon atoms
of a to b. Specific examples of the Ca-b alkoxy may include methoxy group, ethoxy 15 group, n-propyloxy group, i-propyloxy group, n-butyloxy group, i-butyloxy group,
s-butyloxy group, and tert-butyloxy group and the like. Each of these groups is selected
in a range of the specified number of carbon atoms.
[0173] The expression of halo (Ca~b) alkoxy in the present specification is a
haloalkyl-O- group in which this haloalkyl is the above meaning haloalkyl made of the 20 number of carbon atoms of a to b. Specific examples of the halo (Ca-b) alkoxy may
include difluoromethoxy group, trifluoromethoxy group, chlorodiiluoromethoxy group,
bromodifiuororriethoxy group, 2-fluoroethoxy group, 2-chloroethoxy group,
2,2,2-trifluoroethoxy group, 1,1,2,2-tetrafluoroethoxy group,
2-chioro-l,l,2-trifhioroethoxy group, and 1,1,2,3,3,3-hexafluoropropyloxy group and the 25 like. Each of these groups is selected in a range of the specified number of carbon
atoms.
[0174] The expression of Ca-b alkylthio in the present specification is an alkyl-S-
group in which this alkyl is the above meaning alkyl made of the number of carbon atoms
of a to b. Specific examples of the Ca-b alkylthio may include methylthio group,

35 ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, i-butylthio
group, s-butylthio group, and tert-butylthio group and the like. Each of these groups is
selected in a range of the specified number of carbon atoms.
[0175] The expression of Ca_b alkylsulfinyl in the present specification is an
5 alkyl-S(O)- group in which this alkyl is the above meaning alkyl made of the number of
carbon atoms of a to b. Specific examples of the Ca-b alkylsulfinyl may include
methylsulfinyl group, ethylsulfinyl group, n-propylsulfinyl group, i-propylsulfinyl group,
n-butylsulflnyl group, i-butylsulfinyl group, s-butylsulfmyl group, and tert-butylsulfinyl
group and the like. Each of these groups is selected in a range of the specified number
10 of carbon atoms.
[0176] The expression of Ca-b alkylsulfonyl in the present specification is an alkyl-SCV group in which this alkyl is the above meaning alkyl made of the number of carbon atoms of a to b. Specific examples of the Ca-b alkylsulfonyl may include methylsulfonyl group, ethylsulfonyl group, n-propylsulfonyl group, i-propylsulfonyl
15 group, n-butylsulfonyl group, i-butylsulfonyl group, s-butylsulfonyl group, and
tert-butylsulfonyl group and the like. Each of these groups is selected in a range of the specified number of carbon atoms.
[0177] The expression of Ca-b alkoxycarbonyl in the present specification is an alkyl-OC(O)- group in which this alkyl is the above meaning alkyl made of the number
20 of carbon atoms of a to b. Specific examples of the Ca_b alkoxycarbonyl may include methoxycarbonyl group, ethoxycarbonyl group, n-propyloxycarbonyl group, i-propyloxycarbonyl group, n-butoxycarbonyl group, i-butoxycarbonyl group, and tert-butoxycarbonyl group and the like. Each of these groups is selected in a range of the specified number of carbon atoms.
25 [0178] The expression of Ca-b alkylcarbonyl in the present specification is an
alkyl-C(O)- group in which this alkyl is the above meaning alkyl made of the number of carbon atoms of a to b. Specific examples of the Ca-b alkylcarbonyl may include acetyl group, propionyl group, butyryl group, isobutyryl group, valeryl group, isovaleryl group, 2-methylbutanoyl group, pivaloyl group, hexanoyl group, and heptanoyl group and the

36 like. Each of these groups is selected in a range of the specified number of carbon
atoms.
[0179] The expression of Ca-b alkylhnino in the present specification is an
alkyl-N= group in which this alkyl is the above meaning alkyl made of the number of
5 carbon atoms of a to b. Specific examples of the Ca-b alkyiimino may include
methylimino group, ethylimino group, n-propylimino group, i-propylimino group,
n-butylimino group, i-butylimino group, and s-butylimino group and the like. Each of
these groups is selected in a range of the specified number of carbon atoms.
[0180] The expression of Ca-b alkoxyimino in the present specification is an
10 alkoxy-NN group in which this alkoxy is the above meaning alkoxy made of the number of carbon atoms of a to b. Specific examples of the Ca-b alkoxyimino may include methoxyimino group, ethoxyimino group, n-propyloxyimino group, i-propyloxyimino group, and n-butyloxyimino group and the like. Each of these groups is selected in a range of the specified number of carbon atoms.
15 [0181] The expression of Ca-b alkylidene in the present specification is a linear
or branched hydrocarbon group made of the number of carbon atoms of a to b and bonded with a double bond. Specific examples of the Ca„b"alkylidene may include methylidene group, ethylidene group, propylidene group, and 1 -methylethylidene group and the like. Each of these groups is selected in a range of the specified number of
20 carbon atoms.
[0182] The expression of "(Ca-b) alkyl arbitrarily substituted with R5", "(Ca.b) alkyl arbitrarily substituted with R15", "(Ca-b) alkyl arbitrarily substituted with R15b"5 "(Ca-b) alkyl arbitrarily substituted with R20", "(Ca_b) alkyl arbitrarily substituted with R35", or "(Ca-b) alkyl arbitrarily substituted with R 5" hi the present specification is the above
25 meaning alkyl group made of the carbon number of a to b in which the hydrogen atoms bonded to the carbon atoms are arbitrarily substituted with any R5, R15, Ri5b, R20, R35, or R45. Each of these groups is selected in a range of the specified number of carbon atoms. At this time, when two or more substituents R5s, R15s, Rl5bs, R20s, R35s, or R45s are contained in each (Ca.b) alkyl group, each R5, R15, R!5b, R20, R35, or R45 may be the same

37 as or different from each other.
[0183] The expression of "(Ca-b) cycloalkyl arbitrarily substituted with R5",
"(Ca-b) cycloalkyl arbitrarily substituted with R1S", "(Ca-b) cycloalkyl arbitrarily
substituted with R15 ", or "(Ca-b) cycloalkyl arbitrarily substituted with R45" in the present
5 specification is the above meaning cycloalkyl group made of the carbon number of a to b
in which the hydrogen atoms bonded to the carbon atoms are arbitrarily substituted with
any R5, R15, R15b, or R45. Each of these groups is selected in a range of the specified
number of carbon atoms. At this time, when two or more substituents R5s, R s, R 5 s,
or R45s are contained in each (Ca-b) cycloalkyl group, each R5, R15, R15 , or R 5 may be
10 the same as or different from each other. The substituted positions may be at a ring structure part, at a side chain structure part, or at both of them.
[0184] The expression of "(Ca-b) alkenyl arbitrarily substituted with R", "(Ca-b) alkenyl arbitrarily substituted with R15", "(Ca-b) alkenyl arbitrarily substituted with R15 ", or "(Ca-b) alkenyl arbitrarily substituted with R45" in the present specification is the above
15 meaning alkenyl group made of the carbon number of a to b in which the hydrogen atoms bonded to the carbon atoms are arbitrarily substituted with any R5,R", R15 , or R45. Each of these groups is selected in a range of the specified number of carbon atoms. At this time, when two or more substituents R5s, R15s, R15bs, or R45 s are contained in each (Ca-b) alkenyl group, each R , R 5, R15 , or R45 may be the same as or different from each
20 other.
[0185] The expression of "(Ca.b) cycloalkenyl arbitrarily substituted with R5", "(Ca-b) cycloalkenyl arbitrarily substituted with R15", "(Ca.b) cycloalkenyl arbitrarily substituted with RI5b", or "(Ca-b) cycloalkenyl arbitrarily substituted with R45" in the present specification is the above meaning cycloalkenyl group made of the carbon
25 number of a to b in which the hydrogen atoms bonded to the carbon atoms are arbitrarily substituted with any R5, R , R 5 , or R 5. Each of these groups is selected in a range of the specified number of carbon atoms. At this time, when two or more substituents R5s, R15s, R15bs, or R45s are contained in each (Ca-b) cycloalkenyl group, each R5, R15, R,5b, or R " may be the same as or different from each other. The substituted positions may be

38 at a ring structure part, at a side chain structure part, or at both of them.
[0186] The expression of "(Ca-b) alkynyl arbitrarily substituted with R5", "(Ca.b)
alkynyl arbitrarily substituted with R15", "(Ca-b) alkynyl arbitrarily substituted with R15 ",
or "(Ca-b) alkynyl arbitrarily substituted with R 5" in the present specification is the above
5 meaning alkynyl group made of the carbon number of a to b in which the hydrogen atoms
bonded to the carbon atoms are arbitrarily substituted with any R5, R15, R15b, or R45.
Each of these groups is selected in a range of the specified number of carbon atoms. At
this time, when two or more substituents R5s, R 5s, R15 s, or R45s are contained in each
(Ca_b) alkynyl group, each R5, R15, R15b, or R45 may be the same as or different from each
10 other.
[0187] Specific examples of the expression of "R optionally forms a 3-membered ring to an 8-membered ring together with a nitrogen atom to which R3 and are bonded by forming a C2-7 alkylene chain or a C2-7 alkenylene chain together with R4, and at this time, the alkylene chain or the alkenylene chain optionally contain one
15 oxygen atom, one sulfur atom, or one nitrogen atom" include aziridine, azetidine, azetidin-2-one, pyrrolidine, pyrrolidin-2-one, oxazolidine, oxazolidin-2-one, oxazolidine-2-thione, thiazolidine, thiazolidin-2-one, thiazolidine-2-thione, imidazolidine, imidazolidin-2-one, imidazolidine-2-thione, piperidine, piperidin-2-one, piperidine~2-thione, 2H-3,4,5,6-tetrahydro-l,3-oxazin-2-one,
20 2H-3,4,5,6-tetrahydro-l,3-oxazine-2-thione, morpholine,
2H-3,4,5,6-tetrahydro-l,3-thiazin-2-one, 2H-3,4,5,6-tetrahydro-l,3-thiazine-2-thione, thiomorpholine, perhydropyrimidine-2-one, piperazine, homopiperidine, homopiperidin-2-one, heptamethyleneimine, 1,2-dihydropyridine, 1,2-dihydropyrimidine, 1,4-dihydropyridine, 2,3-dihydro-lH-imidazole, 2,3-dihydrothiazole, 2,3-dibydrooxazole,
25 4,5-dmydro-lH-pyrazole, 2,5-dihydro-lH-pyrrole, 1,2,3,4-tetrahydropyridine,
1,2,3,4-tetrahydropyrimidine, and 1,2,3,4-tetrahydropyridazine and the like. Each of these groups is selected in a range of the specified number of carbon atoms.
[0188] Specific examples of the expression of "R18b optionally forms a 3-membered ring to an 8-membered ring together with a nitrogen atom to which R18b and

39 R19b are bonded by forming a C2-7 alkylene chain together with R , and at this time, the
alkylene chain contain one oxygen atom, one sulfur atom, or one nitrogen atom" include
aziridine, azetidine, azetidin-2-one, pyrrolidin, pyrrolidin-2-one, oxazolidine,
oxazolidin-2-one, oxazolidine-2-thione, thiazolidine, thiazolidin-2-one,
5 thiazolidine-2-thione, imidazolidine, fmidazolidin-2-one, imidazolidine-2-thione,
piperidine, piperidin-2-one, piperidine-2-thione, 2H-3,4,5,6-tetrahydro-l,3-oxazin-2-one,
2H-3,4,5,6-tetrahydro-l,3-oxazine-2-thione, morpholine,
2H-3!4,5,6-tetrahydro-l,3-thiazin-2-one, 2H-3,4,5,6-tetrahydro-l,3~thiazine-2-thione,
thiomorpholine, perhydropyrimidin-2-one, piperazine, homopiperidine,
10 homopiperidin-2-one, and heptamethyleneimine and the like. Each of these groups is selected in a range of the specified number of carbon atoms.
[0189] Subsequently, the production method of the compound of the present invention will be described below. In Production Method A to Production Method K, A1 in formulas is a hydrogen atom, C1-6 alkyl, (C1-6) alkyl arbitrarily substituted with R, C3-8
15 cycloalkyl, (C3-8) cycloalkyl arbitrarily substituted with R, C2-6 alkenyl, C3-8
cycloalkenyl, (C3-8) cycloalkenyl arbitrarily substituted with R, (C2-6) alkenyl arbitrarily substituted with R5, C2-6 alkynyl, (C2-6) alkynyl arbitrarily substituted with R5, -S(0)r2R1, -C(0)OR1, -C(S)OR\ -C(0)SR1, -C(S)SR1, -C(0)R2, -C(S)R2, -C(0)N(R4)R3, -C(S)N(R4)R3, -S(0)2N(R4)R3, -P(0)(OR1)2, or -P(S)(OR1)2 and R1, R5, R2, R3, R4 and r2
20 have the same meanings as defined above. [0190] Production Method A

40


.8b i?9b



In the compounds of the present invention, the compound of Formula (1-1) of the present invention [wherein Q, A1, R6, R8a, R8b, R9a, R9b, Z, m, n, and q have the same meanings as defined above.] and the compound of Formula (1-2) of the present invention 5 [Q, A , R , R a, R , R a, R , Z, m, n, and q have the same meanings as defined above.] can be produced by reacting the compound of Formula (1-1-a) with a compound of Formula (7-1) [wherein Ja is a leaving group such as a halogen atom, -OSC^Me, and -OS02CF3andA1hasthe same meaning as defined above.].
Some of the compounds of Formula (7-1) are known compounds and some of the 10 compounds are commercially available. The compounds other than the known
compounds or the commercially available compounds can be synthesized in accordance with methods described in documents.
In this reaction, the compound of Formula (7-1) can be used in a range of 0.5 equivalent to 50 equivalents relative to 1 equivalent of the compound of Formula (1-1-a). 15 Bases such as triethylamine, pyridine, 4-(dimethylamino)pyridme5
l,8~diazabicyclo[5.4.0]-7-undecene, n-butyllithium, lithium diisopropylamide, lithium bis(trimethylsilyl)amide, sodium bis(trimethylsilyl)amide, potassium
potassium hydroxide, sodium carbonate, and potassium carbonate can be used, if
This reaction may be carried out in the absence of a solvent or may be carried out

41 using a solvent. Examples of the solvent may include polar solvents such as
N,N-dimethylformamide, N,N-dimethylacetamide, acetonitrile, dimethylsulfoxide, and
l,3-dimethyl-2-imidazolinone; alcohols such as methanol, ethanol, propanol, 2-propanol,
and ethylene glycol; ethers such as diethyl ether, tetrahydrofuran, and diphenyl ether;
5 aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons
such as methylene chloride, chloroform, and carbon tetrachloride; and aliphatic
hydrocarbons such as pentane and n-hexane. These solvents may be used singly or in
combination of two or more of them.
As the reaction temperature, any temperature from -80°C to the reflux temperature
10 of the reaction mixture can be set. The reaction time varies depending on the
concentration of the reactant and the reaction temperature, and usually the time may be
set in a range of 5 minutes to 100 hours,
[0191] Production Method B

R7ONH, (3)

RBflR'

(1-1-al)

OH

N

15

In the compounds of Formula (1-1-a), the compound of Formula (1-1-a2) of the present invention [wherein R , R , R8a, R , R a, R9 , Z, m, n, and q have the same
meanings as defined above.] can be produced by reacting the compound of Formula (1-1-al) [wherein R , R a, R , R a, R , Z, m, n, and q have the same meanings as defin above.] with a compound of Formula (3) [wherein R7 has the same meaning as defined

compounds
compounds are commercially available.
(3) are known compounds and some The compounds other than the known
compounds or the commercially available compounds can be synthesized in accordance
with methods described in documents.
25 in this reaction, the compound of Formula (3) can be used in a range of 0.1
equivalent to 100 equivalent relative to 1 equivalent of the compound of Formula

42 (1-1-al). Bases such as potassium carbonate, triethylamine, pyridine, and
4-(dimethylamino)pyridine can be used, if necessary.
This reaction may be carried out in the absence of a solvent or may be carried out
using a solvent. Examples of the solvent may include polar solvents such as
5 N,N-dimethylformamide, N,N~dimethylacetamide, acetonitrile, dimetliylsulfoxide, and
l,3-dimethyl-2-imidazoimone; alcohols such as methanol, ethanol, propanol, 2-propanol,
and ethylene glycol; ethers such as diethyl ether, tetrahydrofuran, and diphenyl ether;
aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons
such as methylene chloride, chloroform, and carbon tetrachloride; and aliphatic
10 hydrocarbons such as pentane and n-hexane. These solvents may be used singly or in
combination of two or more of them.
As the reaction temperature, any temperature from -80°C to the reflux temperature
of the reaction mixture can be set. The reaction time varies depending on the
concentration of the reactant and the reaction temperature, and usually the time may be
15 set in a range of 5 minutes to 100 hours.
[0192] Production Method C

In the compounds of Formula (1-1), the compound of Formula (1-1-al) of the present invention can be obtained by hydrolyzing the compound of Formula (1-1-b)
20 [wherein R , R7, R a, R b, R*a, R , Z, m, n, and q have the same meanings as defined
above, A is Ci_6 alkyl or (Ci^) alkyl arbitrarily substituted with R , and R has the same meaning as defined above.].
in this reaction, solvents such as water, methanol, ethanol, dichloromethane, chloroform, diethyl ether, tetrahydrofuran, 1,4-dioxane, acetonitrile, and acetone may be

43 used, if necessary. These solvents may be used singly or in combination of two or more
of them.
The reaction can be carried out in the presence of 0.1 equivalent to 20 equivalents
of an acid such as hydrochloric acid, sulfuric acid, or p-toluenesulfonic acid relative to 1
5 equivalent of the compound of Formula (1-1-b), if necessary.
As the reaction temperature, any temperature from -80°C to the reflux temperature
of the reaction mixture can be set. The reaction time varies depending on the
concentration of the reactant and the reaction temperature, and usually the time may be
set in a range of 5 minutes to 100 hours.
10 [0193] Production Method D
f

In the compounds of Formula (1-1), the compound of Formula (1-1-b) of the
present invention [wherein R , R , R a, R , R a, R , Z, m, n and q have the same 15 meanings as defined above, A is Ci-6 alkyl or (Ci-e) alkyl arbitrarily substituted with R5, and R has the same meaning as defined above.] can be produced by reacting the compound of Formula (4) [wherein Z and q have the same meanings as defined above, A3 is Ci-6 alkyl or (Ci^) alkyl arbitrarily substituted with R', and R3 has the same meaning as defined above.] with the compound of Formula (5) [wherein Ja, R6, R7, R8a, R8b, R9a, R9b, 20 m, and n have the same meanings as defined above.].
Some of the compounds of Formula (4) are known compounds. The compounds other than the known compounds can be produced in accordance with the known methods described in, for example, Chemische Berichte, 1983, Vol. 116, P. 119.
Some of the compounds of Formula (5) are known compounds. The compounds

44
other than the known compounds can be produced in accordance with the known methods described in, for example, Synthesis, 1982, P. 305.
In this reaction, the compound of Formula (5) can be used in a range of 0.5 equivalent to 50 equivalents relative to 1 equivalent of the compound of Formula (4). 5 Bases such as n-butyllithium, lithium diisopropylamide, lithium bis(trimethylsilyl)amide, sodium bis(trimethylsilyl)amide, potassium bis(trhnethylsilyl)amide, sodium hydride, sodium methoxide, and potassium carbonate can be used, if necessary. This reaction may be carried out in the absence of a solvent or may be carried out using a solvent. Examples of the solvent may include polar solvents such as N,N-dimethylformamide,
10 N,N-dimethylacetamide, dimethylsulfoxide, l-methyl-2-pyrrolidone, and
l,3-dimethyl-2-imidazolinone; alcohols such as methanol, ethanol, propanol, 2-propanol, and ethylene glycol; ethers such as diethyl ether, tetrahydrofuran, and diphenyl ether; and aliphatic hydrocarbons such as pentane and n-hexane. These solvents may be used singly or in combination of two or more of them.
15 As the reaction temperature, any temperature from -80°C to the reflux temperature
of the reaction mixture can be set. The reaction time varies depending on the concentration of the reactant and the reaction temperature, and usually the time may be set in a range of 5 minutes to 100 hours. Production Method E

25

The compound of Formula (l-l-a3) of the Q, Z, and q have the same meanings as defined compound of Formula (9) [wherein Z and q have with the compound of Formula (10) [wherein R , as defined above.].

invention [wherein R6, R8a, R9a, .] can be produced by reacting the same meanings as defined above.] , R a, and Q have the same meanings

45 Some of the compounds of Formula (9) are known compounds. The compounds
other than the known compounds can be produced in accordance with the known
methods described in, for example, WO 2009/019005 Pamphlet.
Some of the compounds of Formula (10) are known compounds and some of the
5 compounds are commercially available. The compounds other than the known
compound or the commercially available compounds can be synthesized in accordance
with methods described in documents.
In this reaction, the compound of Formula (10) can be used in a range of 0.5
equivalent to 50 equivalents relative to 1 equivalent of the compound of Formula (9).
10 Bases such as triethylamine, pyridine, 4-(dimethylamino)pyridine,
l,8-diazabicyclo[5.4.0]~7-undecene, n-butyllithium, lithium diisopropylamide, lithium bis(trimethylsilyl)amide, sodium bis(trimethylsilyl)amide, potassium bis(trimethylsilyl)amide, sodium hydride, sodium methoxide, sodium hydroxide, potassium hydroxide, sodium carbonate, and potassium carbonate can be used, if
15 necessary.
This reaction may be carried out in the absence of a solvent or may be carried out using a solvent. Examples of the solvent may include polar solvents such as N,N-dimethylformaniide, N,N-dimethylacetamide, acetonitrile, dimethylsulfoxide, and l,3-dimethyl-2-irnidazolinone; alcohols such as methanol, ethanol, propanol, 2-propanol,
20 and ethylene glycol; ethers such as diethyl ether, tetrahydrofuran, and diphenyl ether;
aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as methylene chloride, chloroform, and carbon tetrachloride; and aliphatic hydrocarbons such as pentane and n-hexane. These solvents may be used singly or in combination of two or more of them.
25 [0195] Production Method F


46 In the compounds of Formula (1-1-a), the compound of Formula (l-l-a5) of the
present invention [wherein R , R a, Q, Z, and q have the same meanings as defined
above.] can be obtained by hydrolyzing and then decarboxylating the compound of
Formula (l-l-a4) [wherein R6, R8a, Q, Z, and q have the same meanings as defined above,
5 R9a"2 is -C(0)OR16a, and R16a has the same meaning as defined above.].
In this reaction, solvents such as water, methanol, ethanol, dichloromethane,
chloroform, diethyl ether, tetrahydrofuran, 1,4-dioxane, acetonitrile, and acetone may be
used, if necessary. These solvents may be used singly or in combination of two or more
of them.
\ 0 This reaction can be carried out in the presence of 0.1 equivalent to 20 equivalents
of an acid such as hydrochloric acid, sulfuric acid, or p-toluenesulfonic acid or a base
such as sodium hydroxide, potassium hydroxide, sodium carbonate, and potassium
carbonate relative to 1 equivalent of the compound of Formula (l-l-a4), if necessary
As the reaction temperature, any temperature from -80°C to the reflux temperature
15 of the reaction mixture can be set. The reaction time varies depending on the
concentration of the reactant and the reaction temperature, and usually the time may be
set in a range of 5 minutes to 100 hours.
[0196] Production Method G

20 In the compounds of Formula (1-1 -a), the compound of Formula (1-1 -a?) of the
present invention [wherein R6, R7, R8a, R8b, R9a, R9b, Za, Ze, m, and n have the same meanings as defined above and Zc~2 has the same meaning as defined below.] can be produced by reacting the compound of Formula (I-l-a6) [wherein R6, R7, R8a, R8b, R9a, R , Za, Ze, m, and n have the same meanings as defined above, and J is a leaving grouj
25 such as a halogen atom, -OSt^Me, -OSO2CF3.] with the compound of Formula (11)
[wherein Zc~ is C2-6 alkynyl, (C2-6) alkynyl arbitrarily substituted with R45, phenyl, and

47 phenyl substituted with (Z3)q3, Jc is -C(0)OH, -Sn(Ci-6 alkyl)3, -B(OH)2, and the like, and
R4j, Z3 and q3 have the same meanings as described above.] in the presence of a catalyst
and a base.
The amount of the compound of Formula (11) can be used in a range of 0.5
5 equivalent to 50 equivalents relative to 1 equivalent of the compound of Formula
(l-l-a6).
Some of the compounds of Formula (11) used here are known compounds and some
of the compounds are commercially available. The compounds other than the known
compound or the commercially available compounds can be synthesized in accordance
10 with methods described in documents.
Examples of the catalyst used in this reaction may include palladium catalysts such
as palladium-carbon, palladium chloride, palladium acetate, bis(triphenylphosphine)
palladium dichloride, tetrakis(triphenylphosphine) palladium, and
[l,r-bis(diphenylphosphino)ferrocene] palladium (II) dichloride dichloromethane adduct,
15 and copper catalysts such as metal copper, copper acetate (monovalent), copper acetate
(divalent), copper oxide (monovalent), copper oxide (divalent), copper iodide, copper
bromide, and copper chloride. These catalysts can be used singly or in combination of
two or more of them. The amount of the catalyst to be used can be used in a range of
0.001 equivalent to 1.0 equivalent relative to 1 equivalent of the compound of Formula
20 (l-l-a6). Ligands such as 1,4-bis (diphenylphosphino)butane can be used in the range
of 0.001 equivalent to 10 equivalents relative to the catalyst
Examples of the base to be used may include tertiary amine compounds such as
pyridine, dlisopropylethylamine, and triethylamine and inorganic bases such as sodium
hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium
25 carbonate, sodium hydrogen carbonate, and tripotassium phosphate. The amount of the
base to be used can be used in a range of 0.1 equivalent to 10.0 equivalents relative to 1
equivalent of the compound of Formula (11).
This reaction may be carried out in the absence of a solvent or may be carried out
using a solvent. Example of usable solvents may include polar solvents such as

N,N-dimethylformamide, N,N-dimethylacetamide, acetonitrile, dimethylsulfoxide, l,3-dimethyl-2-imidazolinone, and water; alcohols such as methanol, ethanol, propanol, 2-propanol, and ethylene glycol; ethers such as diethyl ether, tetrahydrofuran, and diphenyl ether; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated 5 hydrocarbons such as methylene chloride, chloroform, and carbon tetrachloride; and aliphatic hydrocarbons such as pentane and n-hexane. These solvents may be used singly or in combination of two or more of them.
As the reaction temperature, any temperature from -80°C to the reflux temperature of the reaction mixture can be set. The reaction time varies depending on the 10 concentration of the reactant and the reaction temperature, and usually the time may be set in a range of 5 minutes to 100 hours. [0197] Production Method H


'N^-^

15

In the compounds of Formula (1-1-a), the compound of Formula (l-l-a8) of the present invention [wherein R6, R7, R8a, R8\ R9a, R9b, Za, Ze, X1, g3, m, and n have the same meanings as defined above.] can be produced by reacting the compound of Formula (l-l-a6) [wherein R6, R7, R8a, R8h, R9a, R9b, Za, Ze, m, and n have the same meanings as defined above, and J is a leaving group such as a halogen atom, -OSC^Me, -OSO2CF3.] with the compound of Formula (12) [wherein X1 andg3 have the same meanings as defined above.] in the presence of a catalyst and a base.
The amount of the compound of Formula (12) can be used in a range of 0.5

(l-l-a6).
Some of the compounds of Formula (12) used here are known compounds and some 25 of the compounds are commercially available. The compounds other than the known

49 compound or the commercially available compounds can be synthesized in accordance
with methods described in documents.
Examples of the catalyst used in this reaction may include palladium catalysts such
as palladium-carbon, palladium chloride, palladium acetate, bis(triphenylphosphine)
5 palladium dichlonde, tetrakis(triphenylphosphine) palladium, and
[l,r-bis(diphenylphosphino)ferrocene] palladium (II) dichloride dicliloromethane adduct,
and copper catalysts such as metal copper, copper acetate (monovalent), copper acetate
(divalent), copper oxide (monovalent), copper oxide (divalent), copper iodide, copper
bromide, and copper chloride. These catalysts can be used singly or in combination of
10 two or more of them. The amount of the catalyst to be used can be used in a range of 0.001 equivalent to 1.0 equivalent relative to 1 equivalent of the compound of Formula (l-l-a6). Ligands such as N,N'-dimethylethylenediamme and
N,N'~dimethylcyclohexane-l ,2-diamine can be used in the range of 0.001 equivalent to 10 equivalents relative to the catalyst.
15 Examples of the base to be used may include tertiary amine compounds such as
pyridine, diisopropylethylamine, and triethylamine and inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydrogen carbonate, and tripotassium phosphate. The amount of the base to be used can be used in a range of 0.1 equivalent to 10.0 equivalents relative to 1
20 equivalent of the compound of Formula (12).
This reaction may be carried out in the absence of a solvent or may be carried out using a solvent. Example of usable solvents may include polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, acetonitrile, dimethylsulfoxide, l,3-dimethyl-2-imidazolinone, and water; alcohols such as methanol, ethanol, propanol,
25 2-propariol, and ethylene glycol; ethers such as diethyl ether, tetrahydrofuran, and
diphenyl ether; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as methylene chloride, chloroform, and carbon tetrachloride; and aliphatic hydrocarbons such as pentane and n-hexane. These solvents may be used singly or in combination of two or more of them.

50 As the reaction temperature, any temperature from -80°C to the reflux temperature
of the reaction mixture can be set. The reaction time varies depending on the
concentration of the reactant and the reaction temperature, and usually the time may be
set in a range of 5 minutes to 100 hours.
5 The reaction of Production Method A to Production Method IT may be carried out
under the atmosphere of inert gas such as nitrogen and argon, if necessary.
In Production Method A to Production Method H, usual post-treatment of the
reaction mixture after completion of the reaction such as direct concentration,
concentration after dissolving in an organic solvent and washing with water, or
10 concentration after pouring in ice-water and extracting with an organic solvent can give the target compound of the present invention. When purification is required, the compound can be separated and purified by any purification method such as recrystallization and preparative isolation by column chromatography, thin layer chromatography, and liquid chromatography.
15 [01981 Production Method I


>Bb rj9b


The compounds of Formula (1-3) of the present invention [wherein A1, Q, R6, R8a, R , R9a, Rb,Zm, n, and q have the same meanings as defined above.] can be produced by reacting the mixture of the compound of Formula (13-1) [wherein R90 is a leaving group such as Ci-6 alkoxy, pyrazol-1-yl, and imidazol-1-yl, and A1, Q, R6, R8a, R8b, R9a, R b, R9 , Z, m, n, and q have the same meanings as defined above.] and the compound of

51 Formula (13-2) [wherein R90 is a leaving group such as Ci-6 alkoxy, pyrazol-1 -yl, and
imidazol-1 -yl, and A1, Q, R6, R8a, R8\ R9a, R9b, R90, Z, m, n, and q have the same
meanings as defined above.] with a base.
Examples of the base to be used may include n-butyllithium, lithium diisopropylamide, lithium bis(trimethylsilyl) amide, sodium bis(trimethylsilyl)amide, potassium bis(tnmethylsilyl)amide, sodium hydride, sodium methoxide, potassium carbonate, triethylamine, pyridine, 4-(dimethylamino)pyridine, and l,8-diazabicyclo[5.4.0]-7-undecene. The amount of the base to be used can be used in a range ofO.l equivalent to 10.0 equivalents relative to 1 equivalent of the mixture of the compound of Formula (13-1) and the compound of Formula (13-2).
This reaction may be carried out in the absence of a solvent or may be carried out using a solvent. Example of usable solvents may include polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, l,3-dimethyl-2-imidazolinone, and water; alcohols such as methanol, ethanol, propanol, 2-propanol, and ethylene glycol; ethers such as diethyl ether, tetrahydrofuran, and diphenyi ether; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as methylene chloride, chloroform, and carbon tetrachloride; and aliphatic hydrocarbons such as pentane and n-hexane. These solvents may be used singly or in combination of two or more of them.
As the reaction temperature, any temperature from -80°C to the reflux temperature of the reaction mixture can be set. The reaction time varies depending on the concentration of the reactant and the reaction temperature, and usually the time may be set in a range of 5 minutes to 100 hours.
Amixture of the compound of Formula (13-1) and the compound of Formula (13-2) used in Production Method I can be produced in accordance with a production route described in Reaction Formula 1, for example.
[0199] Reaction Formula 1


Process 1
The mixture of the compound of Formula (174) [wherein A1, Q, R6, R8a, R8b, R9a, R9b, Z, m, n, and q have the same meanings as defined above.] and the compound of 5 Formula (17-2) [wherein A1, Q, R6, R8a, R8b, R9a, R9b, Z, m, n, and q have the same
meanings as defined above.] can be produced by reacting the compound of Formula (15) [wherein A1, Z, and q have the same meanings as defined above.] with the compound of Formula (16) [wherein Q, R6, R8a5 R8b, R9a, R9b, m, and n have the same meanings as defined above.] in accordance with known methods described in documents, for example, 10 the method described in U. S. Patent No. 1981/4283348.
Some of the compounds of Formula (15) used here are known compounds and some
of the compounds are commercially available. The compounds other than the known
compounds or the commercially available compounds can be synthesized in accordance
with methods described in documents.
15 Some of the compounds of Formula (16) are known compounds and can be
produced in accordance with the known methods described in, for example, J. Chem. Soc, 1965, p. 4355. Process 2
The mixture of the compound of Formula (13-1) and the compound of Formula 20 (13-2) can be produced by reacting the mixture of the compound of Formula (17-1) and the compound of Formula (17-2) with a halogenating agent such as thionyl chloride or oxalyl chloride in accordance with known methods described in documents, for example, the method described in Jikken Kagaku Kouza 4th edition (The 4th edition of experimental chemistry) (edited by The Chemical Society of Japan) 1992, Vol. 22, P. 122,

53 and thereafter reacting the resultant mixture with the compound of Formula (18) [wherein
R90 is Ci-6 alkoxy, pyrazol-1-yl, or imidazol-1-yl.] in accordance with known methods
described in documents, for example, the method described in Jikken Kagaku Kouza 4th
edition (The 4th edition of Experimental Chemistry) (edited by The Chemical Society of
5 Japan) 1992, Vol. 22, R 50.
Some of the compounds of Formula (18) used here are known compounds and some
of the compounds are commercially available. The compounds other than the known
compounds or the commercially available compounds can be synthesized in accordance
with methods described in documents.
10 [0200] Production Method J

In the compounds of formula (1-1), the compound of Formula (l-l-b2) of the
present invention [wherein A3, R6, R7, R8a, R8b, R9a, R9b, R10, Z, m, n, and q have the
same meanings as defined above.] can be produced by reacting the compound of Formula 15 (1-1-b) [wherein A3, R6, R7, R8a, R8b, R9a, R9\ Z, m, n, and q have the same meanings as
defined above.] with the compound of Formula (19) [wherein R and Ja have the same
meanings as defined above.].
Some of the compounds of Formula (19) are known compounds and some of the
compounds are commerci 20 compound or the commercially available compounds can be synthesized in accordance
with methods described in documents.
In this reaction, the compound of Formula (19) can be used in a range of 0.5
equivalent to 50 equivalents relative to 1 equivalent of the compound of Formula (1-1-1
Bases such as n-butyllithium, 25 sodium bis(trimethylsilyl)amide, potassium bis(trimethylsilyl)amide, sodium hydride,
sodium methoxide, and potassium carbonate can be used in a range of 0.5 equivalent to

50.0 equivalents relative to 1 equivalent of the compound of Formula (1-1-b), if necessary.
This reaction may be carried out in the absence of a solvent or may be carried out using a solvent. Examples of the solvent may include polar solvents such as N,N-dimelhylformamide, N,N-dimethylacetamide, dimethylsulfoxide, l-methyl-2-pyrrolidone, and l,3-dimethyl-2-imidazolinone; alcohols such as methanol, ethanol, propanol, 2-propanol, and ethylene glycol; ethers such as diethyl ether, tetrahydrofuran, and diphenyl ether; and aliphatic hydrocarbons such as pentane and n-hexane. These solvents may be used singly or in combination of two or more of them.
As the reaction temperature, any temperature from -80°C to the reflux temperature of the reaction mixture can be set. The reaction time varies depending on the concentration of the reactant and the reaction temperature, and usually the time may be set in a range of 5 minutes to 100 hours.
[0201] Production Method K

In the compounds of Formula (1-2), the compound of Formula (l-2-b2) of the present invention [wherein A3, R6, R7, R8a, R8b, R9a, R9b, R11, Z, m, n, and q have the same meanings as defmed above.] can be produced by reacting the compound of Formula (1-2-b) [wherein A3, R6, R7, R8a, R8b, R9a, R9b, Z, m, n, and q have the same meanings as defmed above.] with the compound of Formula (20) [wherein R11 and Ja have the same meanings as defmed above.] in a similar method to Production Method J.
The compound of Formula (1-1-b) used in Production Method J and the compound of Formula (1-2-b) used in Production Method K can be produced as a mixture by Production Method A described above. The compound of Formula (1-1-b2) and the compound of Formula (l-2-b2) can be produced as a mixture by reacting the mixture of the compound of Formula (1-1-b) and the compound of Formula (1-2-b) produced by the

method described in Production Method A without separation, the reaction method being the same as that in Production Method J or Production Method K. The compound of Formula (1-1 -b2) and the compound of Formula (l-2-b2) can be obtained by separating and purifying the mixture by any purification methods such as recrystallization and column chromatography.
[0202] The reaction of Production Method A to Production Method K may be carried out under the atmosphere of inert gas such as nitrogen and argon, if necessary.
[0203] In the reactions of Production Method A to Production Method K, usual post-treatment of the reaction mixture after completion of the reaction such as direct concentration, concentration after dissolving in an organic solvent and washing with water, or concentration after pouring in ice-water and extracting with an organic solvent can give the compound of the present invention. When purification is required, the compound can be separated and purified by any purification method such as recrystallization and preparative isolation by column chromatography, thin layer chromatography, and liquid chromatography.
[0204] Specific examples of the active compound included in the present invention may include the compounds listed in Table 1 to Table 4. The compounds listed in Table 1 to Table 4, however, are the compounds for exemplification, and thus the present invention is not limited to these compounds. In Tables, the expression of the substituent listed in Me is methyl group. Similarly, the expression of Et is ethyl group, n-Pr and Pr-n being normal-propyl group, i-Pr and Pr-i being iso-propyl group, c-Pr and Pr-c being cyclopropyl group, n-Bu and Bu-n being normal-butyl group, s-Bu and Bu-s being secondary-butyl group, i-Bu and Bu-i being iso-butyl group, t-Bu and Bu-t being tertiary-butyl group, c-Bu and Bu-c being cyclobutyl group, n-Pen and Pen-n being normal-pentyl group, c-Pen and Pen-c being cyclopentyl group, n-Hex and Hex-n being normal-hexyl group, c-Hex and Hex-c being cyclohexyl group, n-Oct and Oct-n being octyl group, and Ph being phenyl group.
[0205] In Tables, structures of Dl-2a, Dl»2c, Dl-7a, Dl-7b-l, Dl-7b-2, Dl-7b-3, Dl-7b-4, Dl-lOa, Dl-lla, Dl-llb-1, Dl-llb-2, Dl-llb-3, Dl-1 lb-4, Dl-22a,

Dl-22b-l, Dl-22b-2, Dl-22b-3, Dl-22b-4, Dl-32a, Dl-32b-l, Dl-32b-2, Dl-32b-3, Dl-32b-4, Dl-32b-5, Dl-33a, Dl-33b-l, Dl-33b-2, Dl-33b-3, Dl-33b-4, Dl-34a, Dl-37a, Dl-37b-l, Dl-108a, Dl-108b-l, Dl-108b-2, Dl-108b-3, Dl-108b-4, Dl-108b-5, Dl-108b- 6, Dl-108b-7, Dl-108b-8, Dl-108b-9, Dl-108b-10, DM08b-U, Dl-108b-12, Dl-108b-13, Dl-108b-14, Dl-108b-15, Dl-108b-16, Dl-108b-17, Dl-108b-18, Dl-108b-19,Dl-103-l,DU103-2,Dl-103-3,Dl-103-4,andAltoAn6arethe following structures.

CLAIMS
1. A ketone or oxime compound or a salt thereof of Formula (1):
[wherein B is a ring of any one of B-l, B-2, or B-3;


B-l B-2 B-3
Q is an oxygen atom, a sulfur atom, or NOR7;
A is a hydrogen atom, Ci-6 alkyl, (Ci^) alkyl arbitrarily substituted with R5, C3.8 cycloalkyl, (C3-8) cycloalkyl arbitrarily substituted with R5, C2-6 alkenyl, C3-8 cycloalkenyl, (C3-8) cycloalkenyl arbitrarily substituted with R5, (C2-6) alkenyl arbitrarily substituted with R5, C2-e alkynyl, (C2-6) alkynyl arbitrarily substituted with R5, -S(0)r2R!, -C(0)OR\ -C^OR1, -C(0)SR!, -C(S)SR\ -C(0)R2, -C(S)R2, -C(0)N(R4)R3, -C(S)N(R4)R3, -S(0)2N(R4)R3, -P(0)(OR1)2, or -P(S)(ORi)2;
R1 is Ci^s alkyl, (Ci^) alkyl arbitrarily substituted with R5, C3-8 cycloalkyl, (C3„s) cycloalkyl arbitrarily substituted with R5, C2-6 alkenyl, (C2-6) alkenyl arbitrarily substituted with R , C3.8 cycloalkenyl, (C3-8) cycloalkenyl arbitrarily substituted with R5, C2-6 alkynyl, (C2-6) allcynyl arbitrarily substituted with R5, phenyl, or phenyl substituted with (Z2)q2;

R2 is a hydrogen atom, Ci-8 alkyl, (Ci_6) alkyl arbitrarily substituted with R5, C3-8 cycloalkyl, (C3-s) cycloalkyl arbitrarily substituted with R5, c2.6 alkenyl, (C2-6) alkenyl arbitrarily substituted with R5, C3-8 cycloalkenyl, (C3-8) cycloalkenyl arbitrarily substituted with R5, C2-6 alkynyl, (C2„6) alkynyl arbitrarily substituted with R5, -C(=NOR31)R32, phenyl, phenyl substituted with (Z2)q2, naphthyl, naphthyi substituted with (Z2)q2, Dl-1 to Dl-42, Dl-81, or Dl-84;
R3 and R4 are each independently a hydrogen atom, Ci_6 alkyl, (Ci-e) alkyl arbitrarily substituted with R5, C3-8 cycloalkyl, (C3-8) cycloaJkyl arbitrarily substituted with R5, C2-6 alkenyl, (C2-6) alkenyl arbitrarily substituted with R5, C3-8 cycloalkenyl, (C3-s) cycloalkenyl arbitrarily substituted with R5, C2-6 alkynyl, (C2.6) alkynyl arbitrarily substituted with R5, phenyl, phenyl substituted with (Z2)q2, Dl-32, Dl-33 or Dl-34, or R3 optionally forms a 3- to 8-membered ring together with a njtro^en atom to which R3 and R4 are bonded by forming a C2-7 alkylene chain or a C2.7 alkenylene chain together with R4, 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 Ci-6 alkyl, oxo, or thioxo;
R5 is a halogen atom, cyano, nitro, C3-8 cycloalkyl, --OR31, -S(0)r2R31, -C(0)OR31, -C(0)R32, -N(R34)R33, -Si(R32a)(R32b)R32c5 Phenyl, phenyl substituted with (Z2)q2, Dl-l, Dl-32, Dl-33, or Dl-34, or when two R5s are substituents on a same carbon, the two R5s optionally form oxo, thioxo, imino, Ci-6 alkylimino, Ci.6 alkoxyimino, or Ci_6 alkylidene, together with each other;
R6 is a hydrogen atom, Cj.6 alky], (Ci_6) alkyl arbitrarily substituted with R15, C3-s cycloalkyl, (C3-8) cycloalkyl arbitrarily substituted with R15; c2.6 alkenyl, (C2.6) alkenyl arbitrarily substituted with R15, C3-8 cycloalkenyl, (C3-8) cycloalkenyl arbitrarily substituted with R15, C2~6 alkynyl, (C2.6) alkynyl arbitrarily substituted with R15, -C(-NOR16)Ri7, phenyl, phenyl substituted with (Z')qI, Dl-32, Dl-33, Dl-34, Dl-36, Dl-37,orDl-38;
R7 is a hydrogen atom, Ci-8 alkyl, (Ci.6) alkyl arbitrarily substituted with R15b, C3~s cycloalkyl, (C3.8) cycloalkyl arbitrarily substituted with R15b5 c2.6 alkenyl, (C2.6) alkenyl

246 arbitrarily substituted with R 5 , C3-8 cycloalkenyl, (C3-8) cycloalkenyl arbitrarily
substituted with R15b, C2-6 alkynyl, (C2~6) alkynyl arbitrarily substituted with R15b, phenyl,
or phenyl substituted with (Z')qi;
R8a, R8 , R a, and R9b are each independently a hydrogen atom, cyano, nitro, C1-6 alkyl, halo (Ci_6) alkyl, -OR16a, -S(0)riRI6a, -C(0)OR16a, -C(0)R17a, -C(0)N(R19a)R18a, -C(=NOR16a)R17a, phenyl, or phenyl substituted with (Z1)^;
R10,RuandR12 are each independently a hydrogen atom or C1-6 alkyl;
R15 is a halogen atom, cyano, C3.8 cycloalkyl, -OR , -S(0)riR , phenyl, phenyl substituted with (Z\u Dl-7, Dl-11, Dl-22, Dl-32, Dl-33, or Dl-34;
R15b is a halogen atom, cyano, C3-8 cycloalkyl, halo (C3.8) cycloalkyl, -OR16b,
,16b r^fr\\r\nl€b ^/^\TvT/T»18Kr»19b ^/_WMI 16bYnl7b -VT/TJISKJ, 19b
riR1(,D, -C(0)ORltJD, -C(0)N(RIBn)RiyD, -C(=NORiOD)R1/D, -N(R16D)RiyD, -Si(R32a)(R32b)R32c, phenyl, phenyl substituted with (Z1)^, Dl-32, Dl-33, Dl-34, Dl-36, Dl-37, Dl-38, Dl-81, or Dl-84, or when two R15bs are substituents on a same carbon, the two R 5bs optionally form oxo, thioxo, imino, Ci-6 alkylimino, Ci^ alkoxyimino, or Ci-6 15 alkylidene, together with each other;
R16, RI6a, R16b, R17, R17a, Ri7b, R18a, and R19a are each independently a hydrogen atom or Ci-6 alkyl;
R18b and R19b are each independently a hydrogen atom, Ci_6 alkyl, or (Ci-e) alkyl arbitrarily substituted with R20, or R18b optionally forms a 3- to 8-membered ring together 20 with a nitrogen atom to which R18b and R19b are bonded by forming a C2-7 alkyiene chain or a C2-7 alkenylene chain together with R19b, and at this time, the alkyiene chain or the alkenylene chain optionally contains one oxygen atom, sulfur atom, or nitrogen atom and optionally substituted with oxo or thioxo;
R20 is phenyl or phenyl substituted with (Z )qi;
25 Dl-1 to Dl-42, Dl-81, and Di-84 each are a ring of the following structure;

248 X1 is a halogen atom, cyano, nitro, Ci_6 alkyl, halo (Ci-6) alkyl, or C3-8 cycloalkyl,
when g2, g3, or g4 is an integer of 2 or larger, each X is the same as or different from
each other, and further when two X!s are adjacent, the two adjacent X s optionally form a
6-membered ring together with carbon atoms to which each X is bonded by forming
5 -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, Ci^ alkyl,
halo (Ci-e) alkyl, Ci-e alkoxy, C1.6 alkylthio, Ci-6 alkylsulfinyl, or Q-6 alkylsulfonyl;
Xla is a hydrogen atom or Ci-6 alkyl;
Xlb is C1.6 alkyl;
10 Z is a halogen atom, cyano, nitro, Ci-6 alkyl, (Ci-6) alkyl arbitrarily substituted
with R45, C3-8 cycloalkyl, (C3.8) cycloalkyl arbitrarily substituted with R45, C2-6 alkenyl,
(C2-6) alkenyl arbitrarily substituted with R45, C3-8 cycloalkenyl, (C3.8) cycloalkenyl
arbitrarily substituted with R45, C2-6 alkynyl, (C2-6) alkynyl arbitrarily substituted with R45,
-OR41, -S(0)r3R41, -C(0)OR41, ^C(0)R42, -C(=NOR4I)R42, -N(R44)R43, phenyl, phenyl
15 substituted with (Z3)q3, Dl-1, Dl-2, Dl-7, Dl-10, Dl-11, Dl-22, Dl-32, Dl-33, Dl-34,
Dl-36, Dl-37, or Dl-38, and when q is an integer of 2 or larger, each Z is the same as or
different from each other;
Z1 is a halogen atom, cyano, nitro, Ci-6 alkyl, halo (Ci-e) alkyl, Ci-6 alkoxy, or Ci-6
alkoxycarbonyl, and when ql is an integer of 2 or larger, each Z1 is the same as or
20 different from each other;
Z2 is a halogen atom, cyano, nitro, Ci-6 alkyl, halo (Ci-6) alkyl, -OR51, -S(0)^R519
-C(0)OR51a, -C(0)R52, -C(0)N(R54)R53, -C(S)N(R54)R53, or -N(R54)R53, when q2 is an
'-x
integer of 2 or larger, each Z is the same as or different from each other, and further when two Z s are adjacent, the two adjacent Z s optionally form a 6-membered ring 25 together with carbon atoms to which each Z 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, Ci-6 alkyl, halo (Ci-6) alkyl, Ci-6 alkoxy, Ci-6 alkylthio, Ci-6 alkylsulfinyl, or Ci-e alkylsulfonyl;

249 Z is a halogen atom, cyano, nitro, Ci-e alkyl, halo (Ci-6) alkyl, Ci-6 alkoxy, halo
(Ci_6) alkoxy, Ci-6 alkylthio, Ci-e alkylsulflnyl, or Ci-6 alkylsulfonyl, and when q3 is an
■i
integer of 2 or larger, each Z is the same as or different from each other;
R is a hydrogen atom, Ci-e alkyl, (Ci-e) alkyl arbitrarily substituted with R , 5 -C(0)R , phenyl, phenyl substituted with (Z )q2, naphthyl, or naphthyl substituted with
(Z2)<,2;
R is a hydrogen atom, Ci_6 alkyl, or (Ci-6) alkyl arbitrarily substituted with R ;
R32a, R32b, and R32c are each independently Ci_6 alkyl;
R33 and R34 are each independently a hydrogen atom, C]_6 alkyl, -C(0)OR36, or 10 -C(0)R37;
R is a halogen atom, Ci_6 alkoxy, Ci-6 alkylthio, Ci_6 alkylsulflnyl, Ci_6 alkylsulfonyl, or phenyl;
R36 is Ci.6 alkyl;
R is a hydrogen atom, Cue alkyl, phenyl, or phenyl substituted with (Z )q2;
15 R41 is a hydrogen atom, Ci_6 alkyl, (Ci-6) alkyl arbitrarily substituted with R45,
phenyl, phenyl substituted with (Z3)q3, Dl-32, Dl-33, or Dl-34;
R42 is a hydrogen atom or Ci-6 alkyl;
R43 and R are each independently a hydrogen atom, Ci_6 alkyl, Ci_6
alkoxycarbonyl, or Ci_6 alkylcarbonyl;
20 R45 is a halogen atom, C3.8 cycloalkyl, -OH, Ci-e alkoxy, C1.10 alkoxycarbonyl,
-Si(R32a)(R32b)R32c, phenyl, phenyl substituted with (Z3)q3, Dl-32, Dl-33, or Dl-34, or when two R45s are substituents on a same carbon, the two R45s optionally form oxo, thioxo, imino, Ci_6 alkylimino, Ci_6 alkoxyimino, or Ci-6 alkylidene, together with each
R51 is a hydrogen atom, Ci-6 alkyl, halo (Ci^) alkyl, phenyl, phenyl arbitrarily substituted with a halogen atom, or Dl-39;
R51tt and R52 are each independently a hydrogen atom or Ci_6 alkyl; R53 and R54 are each independently a hydrogen atom, Ci_6 alkyl, or Ci_6

250 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;
gl and p are each independently an integer of 0 or 1;
g2, m, n, rl, 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, ql, q2, and q3 are each independently an integer of 1, 2, 3, 4, or 5].

10

2. The ketone or oxime compound or a salt thereof according to claim 1, wherein B is a ring of either B-l-a or B-2-a; and

Za, Zc and Ze are each independently a hydrogen atom, a halogen atom, cyano, nitro, Ci-6 alky], (Ci-g) alkyl arbitrarily substituted with R45, C3.8 cycloalkyl, (C3-8) cycloalkyl arbitrarily substituted with R45, C2-6 alkenyl, (C2-6) alkenyl arbitrarily substituted with R45, C2-6 alkynyl, (C2-6) alkynyl arbitrarily substituted with R45, -OR41, -S(0)r3R4\ -C(0)OR41, -C(0)R42, -C (-NGR41)R42, -N(R44)R43, phenyl, phenyl substituted with (Z3)q3, Dl-1, Dl-2, Dl-7, Dl-10, DM1, Dl-22, Dl-32, Dl-33, Dl-34, Dl-36,Dl-37,orDl-38.
3. The ketone compound or the salt thereof according to claim 2, wherein Q is an oxygen atom.
4. The oxime compound or a salt thereof according to claim 2, wherein Q is

251
5. The ketone compound or the salt thereof according to claim 3, wherein A is a
hydrogen atom, Ci_6 alkyl, or -C(0)R ;
5 R2 is Ci-8 alkyl;
R6 is Ci.6 alkyl, (Ci-e) alkyl arbitrarily substituted with R15, C3.8 cycloalkyl, C2-6
alkenyl, -C(-NOR16)R17, phenyl, phenyl substituted with (Z1)^, or Dl-32;
R8a is a hydrogen atom, Ci_6 alkyl, -C(0)OR16a, or -C(0)R17a;
R9a is a hydrogen atom or Ci-6 alkyl;
10 R8b and R9b are hydrogen atoms;
R10, R11, and R12 are hydrogen atoms;
R15 is a halogen atom, C3-8 cycloalkyl, -OR16, or phenyl;
R16, R16a, R17, and R17a are each independently Cw alkyl;
X1 is halo (Ci_6) alkyl;
15 Za, Zc and Ze are each independently a hydrogen atom, a halogen atom, Ci-6 alkyl,
C3-8 cycloalkyl, C2-6 alkenyl, (C2-6) alkenyl arbitrarily substituted withR45, C2-6 alkynyl, -OR41, phenyl, phenyl substituted with (Z3)q3, Dl-7, Dl-11, Dl-22, Dl-32, or Dl-37; Z1 is a halogen atom;
Z is a halogen atom, Ci_6 alkyl, halo (Ci-6) alkyl, Ci_6 alkoxy, halo (Ci-e) alkoxy, 20 or Ci-6 aikylthio;
R is Ci-6 alkyl, (Ci-6) alkyl arbitrarily substituted with R , phenyl, Dl-32, or Dl-34;
R45 is a halogen atom, phenyl, or Dl-34;
g2, g3, andp are 0;
25 ql and q3 are integers of 1; and
g4, m, and n are each independently an integer of 0 or 1.
6. The ketone compound or the salt thereof according to claim 5, wherein BisB-l-a;

252 Za is a halogen atom, Ci-6 alkyl, or Ci-6 alkoxy;
Zc is a halogen atom, Ci-e alkyl, C3-8 cycloalkyl, C2-6 alkenyl, (C2-6) alkenyl
arbitrarily substituted with R45, C2_6 allcynyl, -OR41, phenyl, phenyl substituted with (Z3)q3,
Dl-7, Dl-11, Dl-22, Dl-32, or Dl-37; and
5 Ze is a halogen atom or Ci-6 alkyl.
7. The oxime compound or the salt thereof according to claim 4, wherein A is a hydrogen atom, Ci-6 alkyl, (Ci-e) alkyl arbitrarily substituted with R5, C3.8 cycloalkyl, C2-6 alkenyl, (C2-6) alkenyl arbitrarily substituted with R5, C2-6 alkynyl, (C2-6) 10 alkynyl arbitrarily substituted with R5, -SCO^R1, -C(0)OR\ -C(0)SR\ -C(S)OR], -C(0)R2, -C(0)N(R4)R3, -C(S)N(R4)R3, or -S(G)2N(R4)R3;
R1 is C1-8 alkyl, (Ci^) alkyl arbitrarily substituted with R5, C3.8 cycloalkyl, C2-6 alkenyl, phenyl, or phenyl substituted with (Z )q2;
R2 is Ci_8 alkyl, (Ci_6) alkyl arbitrarily substituted with R5, C3-8 cycloalkyl, (C3-8) 15 cycloalkyl arbitrarily substituted with R5, C2-6 alkenyl, (C2-6) alkenyl arbitrarily
substituted with R5, C3.8 cycloalkenyl, (C3.8) cycloalkenyl arbitrarily substituted with R5, C2-6 alkynyl, (C2-6) alkynyl arbitrarily substituted with R5, -C(-NOR31)R32, phenyl, phenyl substituted with (Z2)q2, Dl-5, Dl-6, Dl-8, Dl-10, or Dl-81;
R is Ci-6 alkyl, (Ci-e) alkyl arbitrarily substituted with R , C2-6 alkenyl, phenyl, or
20 phenyl substituted with (Z )q2, or R forms a 5- to 6-membered ring together with a
nitrogen atom to which R3 and R are bonded by forming a C4 or C5 alkylene chain
together with R , and at this time, the alkylene chain optionally contains one oxygen atom
or nitrogen atom and is optionally substituted with Ci-6 alkyl;
R4 is Ci-6 alkyl, C2-6 alkenyl, or phenyl;
25 R5 is a halogen atom, cyano, C3-8 cycloalkyl, -OR31, -S(0)r2R31, -C(0)OR31,
-C(0)R32, -N(R34)R33, -Si(R32a)(R32b)R32c, phenyl, phenyl substituted with (Z2)q2, or Dl-l, or when two R s are substituents on a same carbon, the two R s optionally form Ci-e alkoxyimino together with each other;
R6 is a hydrogen atom, Ci-6 alkyl, (Ci^) alkyl arbitrarily substituted with R15, C3.8

253 cycloaikyl, C2-6 alkenyl, -C(=NOR16)R17, phenyl, phenyl substituted with (Z*)qi or,
Dl-32;
R7 is a hydrogen atom, C1-7 alkyl, (C1-6) alkyl arbitrarily substituted with R15b, C3_8
cycloaikyl, C2-6 alkenyl, C3.8 cycloallcenyl, (C2-6) alkenyl arbitrarily substituted with R15b,
5 C2-6 alkynyl, or phenyl;
R8a is a hydrogen atom, d.6 alkyl, halo (Cw) alkyl, -C(0)OR16a,
-C(-NOR16a)R17a, or phenyl substituted with (Z')ql;
R9a is a hydrogen atom or Q.6 alkyl;
R andR9 are hydrogen atoms;
10 R12 is a hydrogen atom;
R is a halogen atom, C3-8 cycloaikyl, or -OR ;
Ri5b is a halogen atom, cyano, C3-s cycloaikyl, halo (C3-8) cycloaikyl, -OR16b,
-S(0)riR16b, -C(0)OR16b, -C(0)N(R18b)R19b, -C(=NOR16b)R17b, -N(R18b)R19b,
-Si(R32a)(R32b)R32c, phenyl, phenyl substituted with (Z!)qi, Dl-32, or Dl-84;
15 R16, R16a, R17, R17a, and R!7b are each independently Ci-6 alkyl;
RI8b is a hydrogen atom, Ci-6 alkyl, or (Ci-6) alkyl arbitrarily substituted with R20,
or R18b forms a 6-membered ring together with a nitrogen atom to which R18b and R19b are
bonded by forming a C5 alkylene chain together with R19b, and at this time, the alkylene
chain contains one oxygen atom;
20 R is a hydrogen atom or Ci-6 alkyl;
R20 is phenyl substituted with (Z1)^;
X1 is a halogen atom, Ci-6 alkyl, halo (Ci-6) alkyl, or C3.8 cycloaikyl, g3 is an
integer of 2, and further the two adjacent X's form a 6-membered ring together with
carbon atoms to which each X1 is bonded by forming -CH=CHCH=CH-S and at this time,
25 one hydrogen atom bonded to each carbon atom forming the ring is
X a is Ci-6 a!
Za, ZG, and Ze are each independently a hydrogen atom, a halogen atom, cyano, nitro, Ci-6 alkyl, C3-8 cycloaikyl, C2-6 alkenyl, (C2-6) alkenyl arbitrarily substituted with

254 R45, C2-6 alkynyl, (C2.6) alkynyl arbitrarily substituted with R45, -OR41, -S(0)r3R41,
-C(0)OR41, -C(0)R42, -C(=NGR4,)R42, -NCR^R43, phenyl, phenyl substituted with (Z3)q3,
Dl-2, Dl-7, Dl-11, Dl-22, Dl-32, Dl-33, Dl-34, or Dl-37,
Z is a halogen atom, nitro, C1-6 alkyl, halo (Ci-e) alkyl, Ci-e alkoxy, or C1-6
5 alkoxycarbonyl, and when ql is an integer of 2 or larger, each Z is the same as or
different from each other;
Z2 is a halogen atom, cyano, nitro, Ci_6 alkyl, halo (Ci-e) alkyl, -OR51, -S(0)r2R51,
-C(0)OR51a, -C(0)R52, or -C(0)N(R54)R53, when q2 is an integer of 2 or larger, each Z2 is
the same as or different from each other, and further when the two Z s are adjacent, the
10 two adjacent Z s optionally form a 6-membered ring together with carbon atoms to which
each Z 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 is a halogen atom, C1-6 alkyl, halo (Ci-g) alkyl, C1-6 alkoxy, halo (C1-6) alkoxy,
15 or C1-6 alkylthio, and when q3 is an integer of 2 or larger, each Z" is the same as or
different from each other;
R31 is Ci_6 alkyl, (Ci_6) alkyl arbitrarily substituted with R35, -C(0)R37, phenyl,
phenyl substituted with (Z )q2, or naphthyl;
RJ/ is C1.6 alkyl or (Ci.6) alkyl arbitrarily substituted with R"; R33 is -C(0)R37; R34 is Ci.6 alkyl;
R is a halogen atom, Ci-e alkylthio, or phenyl; R is C1-6 alkyl or phenyl;
R is a hydrogen atom, C1-6 alkyl, (Ci-e) alkyl arbitrarily substituted with R , or Dl-32; R42 is C1-6 R43 is Ci.6 R is a hydrogen atom; R 5 is a halogen atom, C3.8 cycloalkyl, -OH, Ci-e alkoxy, CMO alkoxycarbonyl,
.32 ■ ^ „,1 1 „„ /^. A „H„., __!_.._•! l.^*..^ J „JA1_ T»35.
20

255
-Si(R32a)(R32b)R32c, phenyl, or Dl-34;
R51 is Ci_6 alkyl, halo (Ci-6) alkyl, phenyl arbitrarily substituted with a halogen atom, or Dl-39;
R51a is Ci.6 alkyl;
5 R5 andR are each independently Ci-6 alkyl;
g2 is an integer of 0, 1, or 2;
g3 and rl 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;
10 q is an integer of 2 or 3;
ql 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. 15
8. The oxime compound or the salt according to claim 7, wherein
BisB-l-a;
Za is a halogen atom, Q-6 alkyl, Ci-6 alkoxy, or Ci-6 alkylthio; Zc is a hydrogen atom, a halogen atom, cyano, nitro, Ci-6 alkyl, C3-8 cycloalkyl, 20 C2.6 aikenyl, (C2-6) alkenyi arbitrarily substituted with R 5, C2-6 alkynyl, (C2-6) alkynyl
arbitrarily substituted with R45, -OR41, -S(0)r3R41, -C(0)OR4S, -C(0)R42, -C(=NOR41)R42, -N(R44)R43, phenyl, phenyl substituted with (Z3)q3, Dl-2, Dl-7, Dl-11, Dl-22, Dl-32, Dl-33, Dl-34, or Dl-37;
Ze is a halogen atom, Ci-6 alkyl, or Ci_6 alkoxy;
25 X1 is a halogen atom or halo (Ci-a) alkyl; and
g3 is an integer of 0 or 1.
9. An agricultural chemical comprising:
one or more of compounds selected from the ketone or oxime compound or the

salt thereof as claimed in any one of claims 1 to 8 as an active component.
10. A herbicide comprising:
one or more of compounds selected from the ketone or oxime compound or the salt thereof as claimed in any one of claims 1 to 8 as an active component.