TECHNICAL FIELD
[0001] The present invention relates to a novel heterocyclic amide compound and
a salt thereof, and agricultural chemicals, in particular herbicides, containing the
heterocyclic amide compound and the salt thereof as an active component. The
10 agricultural chemical in the present invention means an insecticide/acaricide, a
nematicide, a herbicide, a bactericide and the like in agricultural and horticultural fields.
BACKGROUND ART
15 [0002] For example, a certain type of heterocyclic amide compounds has been
disclosed in Patent Documents 1 to 6. The heterocyclic amide compound according to
the present invention, however, has not been disclosed at all.
Prior Art Documents
Patent Documents
20 [0003] Patent Document 1: International Publication No. 2012/028579 (WO
2012/028579)
Patent Document 2: International Publication No. 2012/123409 (WO 2012/123409)
Patent Document 3: International Publication No. 2012/123416 (WO 2012/123416)
Patent Document 4: International Publication No. 2012/126932 (WO 2012/126932)
25 Patent Document 5: International Publication No. 2013/017559 (WO 2013/017559)
Patent Document 6: International Publication No. 2013/064457 (WO 2013/064457)
SUMMARY OF THE INVENTION
2
Problem to be Solved by the Invention
[0004] An object of the present invention is to provide a chemical substance that
reliably exerts effects on various weeds in a low application amount of the chemical
substance, has reduced land pollution and influence on succeeding crops and has a high
5 level of 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 heterocyclic amide compound of
Formula (1) according to the present invention has excellent herbicidal activity as a
10 herbicide and a high level of safety to target crops as well as almost no adverse effect on
non-target creatures such as mammals, fish, and beneficial insects, and that the compound
is an extremely useful compound, and thus the inventors have accomplished the present
invention.
[0006] More specifically, the present invention relates to the following [1] to
15 [115].
[13
A heterocyclic amide compound of Formula (1):
Q...A
20 [where Q is an aromatic heterocycle of any one of Q-l to Q-5;
5 X is an oxygen atom or a sulfur atom;
Ria is a hydrogen atom, a halogen atom, Ci_6 alkyl, (Ci-e) alkyi optionally
substituted with R6, C3.6 cycloalkyl, (C3.6) cycloalkyl optionally substituted with R6, C2-6
alkenyl, C2_6 alkynyl, C3-6 cycloalkenyl, -C(0)R8, -C(0)ORi6, cyano, -OR9, -S(O)miR]0,
-N(R")R12, -C(=NR12b)R8b, phenyl, phenyl substituted with (R7)p, naphthyl, or any one
10 groupofU-ltoU-25;
Rlb is a hydrogen atom, Ci_6 alkyl, (Ci^) alkyl optionally substituted with R6, C3-6
cycloalkyl, (C3-6) cycloalkyl optionally substituted with R6, C2-6 alkenyl, C2-6 alkynyl,
phenyl, phenyl substituted with (R7)p, naphthyl, 5-6-membered heteroaryl, 5-6-membered
4
heteroaryl (optionally substituted with R and R a), 3-7-membered heterocyclyl, or
3-7-membered heterocyclyl (optionally substituted with R28 and R28a);
RlcisCi_6alkyl;
R2a is a halogen atom, CU6 alkyl, Ci-e haloalkyl, -C(0)R!8, -C(0)OR24, cyano, nitro,
5 -OR19, -SKO^R20, -N (R21)R22, phenyl, or phenyl substituted with (R7)p; when n is an
integer of 2 or more, R2a are optionally the same as or different from each other, and
when two R2a are adjacent, the two adjacent R2a optionally form a 6-membered ring
together with carbon atoms bonded to each R2a by forming -CH=CH-CH-CH-;
R2c is Ci_6 haloalkyl;
10 ; R3 is a hydrogen atom, Cj_6 alkyl, (Ci-e) alkyl optionally substituted with R27, C3^
cycloalkyl, C3.6 halocycloalkyl, C2-6 alkenyl, C2-6 haloalkenyl, C2-6 alkynyl, C2-6
haloalkynyl, -C(0)R25, or -C(0)OR26;
R a is a hydrogen atom, a halogen atom, Ci_6 alkyl, (Ci^) alkyl optionally
substituted with R27, C3-6 cycloalkyl, (C3-6) cycloalkyl optionally substituted with R27,
15 C2-6 alkenyl, C2-6 haloalkenyl, C2.6 alkynyl, C2-6 haloalkynyl, C3-6 cycloalkenyl, -NH2,
C1-6 alkylamino, di(Ci_6 alkyl)amino, -NHC(0)R8, phenyl, phenyl substituted with (R28)r,
5-6-membered heteroaryl, 5-6-membered heteroaryl (optionally substituted with R28 and
R28a), 3-7-membered heterocyclyl, or 3-7-membered heterocyclyl (optionally substituted
with R28 and R28a);
20 R4b is a hydrogen atom, a halogen atom, cyano, nitro, C1-6 alkyl, (Ci-e) alkyl
optionally substituted with R27, C3_6 cycloalkyl, (C3-6) cycloalkyl optionally substituted
with R27, C2-6 alkenyl, C2-6 haloalkenyl, C2-6 alkynyl, C2-6 haloalkynyl, C3_6 cycloalkenyl,
-C(0)OR16, -OR38, -S(0)m3R2°, -NH2, Cl4 alkylamino, di(Cw alkyl)amino, -NHC(0)R8,
phenyl, phenyl substituted with (R28)r, 5-6-membered heteroaryl, 5-6-membered
25 heteroaryl (optionally substituted with R28 and R28a), 3-7-membered heterocyclyl, or
3-7-membered heterocyclyl (optionally substituted with R28 and R28a);
R4c is a hydrogen atom, a halogen atom, C1-6 alkyl, (C1-6) alkyl optionally
substituted with R27, C3.6 cycloalkyl, (C3.6) cycloalkyl optionally substituted with R27,
phenyl, phenyl substituted with (R28)r, 5-6-membered heteroaryl, 5-6-membered
5
heteroaryl (optionally substituted with R28 and R28a), 3-7~membered heterocyclyl, or
3-7-membered heterocyclyl (optionally substituted with R28 and R28a);
R4d is a hydrogen atom, Ci_6 alkyl, or (Ci-e) alkyl optionally substituted with R35;
U-1 to U-6, U-6a, U-7 to U-10, U-lOa, U-ll, U-lla, U-12, U-12a, U-13, U-13a,
U-14 to U-22, U-22a, U-23, U-24, U-25, and U-26 are respective heterocycles of the
following structures;
.5a ,5b R a and R are each independently a hydrogen atom, Ci-6 alkyl, (Ci^) alkyl
optionally substituted with .27 R , C3.6 cycbalkyl, C3^ halocycloalkyl, C2-6 alkenyl, C2-6
7
haioalkenyl, C2-6 alkynyl, C2-6 haloalkynyl, C3-6 cycloalkenyl, phenyl, or phenyl
substituted with (R28)r;
R5c is a hydrogen atom, C1-6 alkyl, or (C1-6) alkyl optionally substituted with R36, or
R5c optionally forms a 6-membered ring together with a nitrogen atom to which R5c is
5 bonded and a carbon atom to which R4d is bonded by forming ~(CH2)4- or
-CH=CH-CH-CH- with R4d;
R6 is a halogen atom, cyano, C3-6 cycloaikyl, -C(0)Rs, -C(0)OR16, -OR13,
-S(0)m2R14
5 phenyl, or phenyl substituted with (R7)p;
R7 is a halogen atom, cyano, nitro, C1-6 alkyl, (Ci^) alkyl optionally substituted with
10 R27, C3-6 cycloaikyl, C3.6 halocycloalkyl, C2-6 aikenyl, C2-6 haioalkenyl, C2-6 alkynyl, C2-6
haloalkynyl, C3.6 cycloalkenyl, Ci^ alkylcarbonyl, C3-6 cycloalkylcarbonyl, Ci_6
haloalkylcarbonyl, C3.6 halocycloalkylcarbonyl, Cj_6 alkoxycarbonyl, C1-6
haloalkoxycarbonyl, d^ alkylaminocarbonyl, Ci^ haloalkylaminocarbonyl, di(Ci_6
alkylamino)carbonyl, -OR15, -S(0)m3R2°, C1-6 alkylaminosulfonyl, di(Ci-6
15 alkyl) amino sulfonyl, -NH2, Ci^ alkylamino, di(JCi_6 alkyl)amino, 5-6-membered
heteroaryl, 5-6-membered heteroaryl (optionally substituted with R28 and R28a),
3-7-membered heterocyclyl, or 3-7-membered heterocyclyl (optionally substituted with
R28andR28a);
R8 is a hydrogen atom, C1-6 alkyl, or -N(Rlla)R12a;
20 R8b is a hydrogen atom or Ci^ alkyl;
R9 is a hydrogen atom, Ci_6 alkyl, or phenyl;
R10 is a hydrogen atom, Ci_6 alkyl, (Ci-e) alkyl optionally substituted with R34, C3-6
cycloaikyl, C3-6 halo cycloaikyl, C2-6 aikenyl, C2-6 haioalkenyl, C2-6 alkynyl, or C2-6
haloalkynyl;
25 R and R are each independently a hydrogen atom, C1-6 alkyl, (C1-6) alkyl
optionally substituted with R , C3-6 cycloaikyl, C2-6 aikenyl, C2-6 haioalkenyl, C2-6
alkynyl, C2-6 haloalkynyl, phenylsulfonyl, phenyl, phenyl substituted with (R7)p, U-7, U-8,
U-9, or U-14 to U-19, or R11 optionally forms a 3-7-membered ring together with a
nitrogen atom to which R11 and R12 are bonded by forming a C2-6 alkylene chain together
8
with R12, and in this case, the alkylene chain optionally contains one O, S, S(O), S(0)2, or
N(R33) and is optionally substituted with an oxo group or a thioxo group;
R1!a and R12a are each independently a hydrogen atom, Ci-e alkyl, or phenyl, or Rlla
optionally forms a 3-7-membered ring together with a nitrogen atom to which Rlla and
5 R12a are bonded by forming a C2.6 alkylene chain together with Ri2a, and in this case, the
alkylene chain optionally contains one O, S, S(0), S(0)2, orN(R33) and is optionally
substituted with an oxo group or a thioxo group;
R12b is -OR19b;
R13 is a hydrogen atom, C1-6 alkyl, (Ci-e) alkyl optionally substituted with R34, C2-6
10 : alkenyl, C2-6 haloalkenyl, C2-6 alkynyl, C2-6 haloalkynyl, ~C(0)R8, or phenyl;
R14 is a hydrogen atom, Ct-6 alkyl, (Cj-e) alkyl optionally substituted with R34, C2-6
alkenyl, C2-6 haloalkenyl, C2-6 alkynyl, C2-6 haloalkynyl, or phenyl;
Ri5 is a hydrogen atom, Ci^ alkyl, (Ci^) alkyl optionally substituted with R27, C3_6
cycloalkyl, C3-6 halocycloalkyl, C2-6 alkenyl, C2-6 haloalkenyl, C2-6 alkynyl, C2_6
15 haloalkynyl, or C3-6 cycloalkenyl; t
R16 is a hydrogen atom, Ci_6 alkyl, or (C^) alkyl optionally substituted with R37;
1 ft
R is a hydrogen atom or Ci^ alkyl;
Ri9 is a hydrogen atom, C1-6 alkyl, or phenyl;
R19b is a hydrogen atom or C1-6 alkyl;
20 R20 is Ci^ alkyl, Ci^ haloalkyl, C3.6 cycloalkyl, C2-6 alkenyl, C2-6 haloalkenyl, C2-6
alkynyl, C2-6 haloalkynyl, or C3-6 cycloalkenyl;
IT1 and R" are each independently a hydrogen atom, C1.6 alkyl, or phenyl, or R
optionally forms a 3-7-membered ring together with a nitrogen atom to which R21 and R
are bonded by forming a C2-6 alkylene chain together with R , and in this case, the
25 alkylene chain optionally contains one O, S, S(O), S(0)2, orN(R39) and is optionally
substituted with an oxo group or a thioxo group;
R24 is a hydrogen atom or C4.6 alkyl;
R25 and R26 are each independently a hydrogen atom, Ci-e alkyl, C1-6 haloalkyl, C3^
cycloalkyl, C3-6 halocycloalkyl, C2-6 alkenyl, C2-6 haloalkenyl, C2-6 alkynyl, C2.6
9
haloalkynyl, C3-6 cycloalkenyl, or phenyl;
R27 is a halogen atom, cyano, nitro, phenyl, phenyl substituted with (R28)r,
-C(0)OR16, -OR29, -S(0)m4R30, 5-6-membered heteroaryl, 5-6-membered heteroaryl
(optionally substituted with R28 and R28a), 3-7-membered heterocyclyl, or 3-7-membered
5 heterocyclyl (optionally substituted with R28 and R28a);
R28 is a halogen atom, cyano, nitro, C^ alkyl, C1-6 haloalkyl, C3-6 cycloalkyl, C3-6
haiocycloaikyl, C2-6 alkenyl, C2-6 haloalkenyl, C2-6 alkynyl, C2_e haloalkynyl, (C1-6
alkoxy) Ci_6 alkyl, -OR31, or -S(0)m4R3°; when t2, t3, t4, t5, t7, t8, or t9 is an integer of 2
or more, R28 are optionally the same as or different from each other; former when two R28
10 " are adjacent, the two adjacent R28 optionally form a 6-membered ring together with
carbon atoms to which each R28 is bonded by forming -CH=CH-CH=CH-;
R28a is C1-6 alkyl, CU6 haloalkyl, (C^ alkoxy) Ci-e alkyl, or ( C ^ alkylthio) Cw
alkyl;
R29, R30, and R31 are each independently a hydrogen atom, Cj-6 alkyl, Ci^ haloalkyl,
15 C3-6 cycloalkyl, C3.6 haiocycloaikyl, C2-6 alkenyl, C2-6 haloalkenyl, C2-6 alkynyl, C2-6
haloalkynyl, C3.6 cycloalkenyl, or phenyl;
R33 is a hydrogen atom or C1-6 alkyl;
R34 is a halogen atom, cyano, C3-6 cycloalkyl, -C(0)R8, -C(0)OR16, -OR33,
-S(0)m6R33, phenyl, phenyl substituted with (R7)P, U-1, U-3, U-7, U-8, U-9, or U-14 to
20 U-25;
R35 is a halogen atom or C[_6 alkoxy;
R36 is a halogen atom or Ci^ alkoxy;
R37 is Ci^ alkoxy,
R38 is Ci-e alkyl, (Ci-e) alkyl optionally substituted with R34, C3-6 cycloalkyl, C3-6
25 haiocycloaikyl, C2-6 alkenyl, C2-6 haloalkenyl, C2-e alkynyl, C2-6 haloalkynyl, C3-6
cycloalkenyl, or phenyl;
R39 is a hydrogen atom or C1-6 alkyl;
tl is an integer of 0 or 1;
ml, m2, m3, m4, m6, and t2 are each independently an integer of 0, 1, or 2;
10
n and t3 are each independently an integer of 0, 1, 2, or 3;
p and r are each independently an integer of 1, 2, 3, 4, or 5;
t4 is an integer of 0,1,2, 3, or 4;
t5 is an integer of 0, 1, 2, 3,4, or 5;
5 t7 is an integer of 0, 1, 2, 3, 4, 5, 6, or 7;
t8 is an integer of 0, 1, 2, 3,4, 5, 6, 7, or 8; and
t9 is an integer of 0, 1,2, 3,4, 5, 6, 7, 8, or 9] or a salt thereof.
[0007] [2]
The heterocyclic amide compound or the salt thereof according to [1], in which W is
10 an aromatic heterocycle of W-l orW-2;and
R2a is a halogen atom, Ci-e alkyl, Ci_6 haloalkyl, -C(0)R18, -C(0)OR24, cyano, nitro,
-OR19, or -S(0)m3R20, and when n is an integer of 2 or more, R2a are optionally the same
as or different from each other.
[0008] [3]
15 The heterocyclic amide compound or the salt thereof according to [2], in which Rlb
is a hydrogen atom, Ci-6 alkyl, (Ci-6) alkyl optionally substituted with R6, C3-6 cycloalkyl,
(C3-6) cycloalkyl optionally substituted with R6, C2-6 alkenyl, C2-6 alkynyl, phenyl, phenyl
substituted with (R7)p, naphthyl, or any one group of U-l to U-25;
R4a is a hydrogen atom> a halogen atom, Ci-e alkyl, (Cj-e) alkyl optionally
20 substituted with R27, C3.6 cycloalkyl, (C3-6) cycloalkyl optionally substituted with R27,
C2-6 alkenyl, C2-6 haloalkenyl, C2-6 alkynyl, C2.6 haloalkynyl, C3_6 cycloalkenyl, -NH2,
C1-6 alkylamino, di(Ci^ alkyl)amino, -NHC(0)R8, phenyl, phenyl substituted with (R28)r,
or any one group of U-l to U-26;
R7 is a halogen atom, cyano, nitro, Ci-e alkyl, (Ci^) alkyl optionally substituted with
25 R27, C3-6 cycloalkyl, C3-6 halo eye loaikyl, C2-6 alkenyl, C2-6 haloalkenyl, C2-6 alkynyl, C2-6
haloalkynyl, C3-6 cycloalkenyl, Ci-6 alkylcarbonyl, C3.6 cycloalkylcarbonyl, Ci-e
haloalkylcarbonyl, C3-6 halo cycloalkylcarbonyl, Ci-6 alkoxycarbonyl, C1-6
haloalkoxycarbonyl, Ci_6 alkylaminocarbonyl, Ci_6 haloalkylaminocarbonyl, di(Ci_6 alkyl
amino)carbonyl, -OR15, -S(0)m3R , Ci-e alkylaminosulfonyl, di(Ci_6 alkyl)aminosulfonyl,
11
-NH2, Ci_6 alkylamino, di(Ci^ alkyl)amino, or any one group of U-l to U-26; and
R27 is a halogen atom, cyano, nitro, phenyl, phenyl substituted with (R28)r,
-C(0)OR16, -OR29, -S(0)m4R3°, or any one group of U-l to U-26.
[0009] [4]
5 The heterocyclic amide compound or the salt thereof according to [3], in which Rla
is a hydrogen atom, a halogen atom, Ci-6 alkyl, (Ci-e) alkyl optionally substituted with R6,
C3-6 cycloalkyl, (C3.6) cycloalkyl optionally substituted with R6, C2-6 alkenyl, C2-6 alkynyl,
C3-6 cycloalkenyl, -C(0)R8, -OR9, -S(0)miR10, -N(Rn)R12, -C(-NR12b)R8b, phenyl,
phenyl substituted with (R7)p, U-3, U-5a, U-6a, U-7, U-8, U-lOa, U-lla, U-12a, or
10 U-13a;
RIb is Ci^ alkyl or (C^) alkyl optionally substituted with R6;
R2a is a halogen atom, C3-6 alkyl, Ci^ haloalkyl, or -S(0)m3R20, and when n is an
integer of 2 or more, R2a are optionally the same as or different from each other;
R3 is a hydrogen atom or Ci_6 alkyl;
15 R4a is a hydrogen atom, Ci-6 alkyl, (Ci-6) alkyl optionally substituted with R27, C3-6
cycloalkyl, phenyl, phenyl substituted with (R )r, or a heterocycle of U-l, U-2, U»7,
U-10a,orU-26;
R4b is d_6 alkyl;
R4c is a hydrogen atom;
20 R4d is C^ alkyl;
R5a is a hydrogen atom, Ci-6 alkyl, (Ci^) alkyl optionally substituted with R27, C2-6
alkenyl, or phenyl;
R5b is a hydrogen atom or Ci^ alkyl;
R5c is Ci^ alkyl, or R5c optionally forms a 6-membered ring together with a nitrogen
25 atom to which R5c is bonded and a carbon atom to which R4d is bonded by forming
~(CH2)4- or -CH=CH-CH-CH- with R4d;
R is a halogen atom, Ci^ alkyl, (Ci-e) alkyl optionally substituted with R , or
-OR15;
R8 is a hydrogen atom;
12
R9 is Ci* alkyl;
R10 is Ci^ alkyl, (Ci-e) alkyl optionally substituted with R34, C3_6 cycloalkyl, C2-6
alkenyl, or C2-6 alkynyl;
R11 is Ci-6 alkyl, (C1-6) alkyl optionally substituted with R34, C3-6 cycloalkyl, C2-6
5 alkenyl, C2-6 alkynyl, phenylsulfonyl, phenyl, phenyl substituted with (R7)P, or U-7;
R12 is a hydrogen atom or C1-6 alkyl;
R11 optionally forms a 5-6-membered ring together with a nitrogen atom to which
R11 and R12 are bonded by forming a C4.5 alkylene chain together with R12, and in this
case, the alkylene chain optionally contains one O, S, S(O), or S(0)2;
10" Rl l a is Ci^ alkyl;
R12a is a hydrogen atom;
R13 is a hydrogen atom, Cf_6 alkyl, (Ci-e) alkyl optionally substituted with R34,
-C(0)R8, or phenyl;
R14 is C1-6 alkyl or (Ci^) alkyl optionally substituted with R34;
15 R15 is C1-6 alkyl;
R19b is C1-6 alkyl;
R20 is C1-6 alkyl;
R27 is a halogen atom, phenyl, phenyl substituted with (R28)r, -OR29, -C(0)OR16, or
-S(0)m4R30;
20 R28 is a halogen atom, Cw alkyl, or -OR31; when t2, t3, t4, t5, or t7 is an integer of 2
or more, R28 are optionally the same as or different from each other; and further when
two R28 are adjacent, the two adjacent R28 optionally form a 6-membered ring together
with carbon atoms to which each R28 is bonded by forming -CH=CH-CH~CH-;
R29 is C1-6 alkyl;
25 R30 is C1-6 alkyl;
R31 is C1-6 alkyl;
R33 is Ci-e alkyl; and
R34 is a halogen atom, cyano, C3^ cycloalkyl, -C(0)R8, -C(0)OR16, -OR33,
-S(0)m6R33, phenyl, phenyl substituted with (R7)P, U-1, U-8, or U-22a.
13
[0010] [5]
The heterocyclic amide compound or the salt thereof according to [4], in which Q is
an aromatic heterocycle of Q-l; and
W is an aromatic heterocycle ofW-1.
[0011] [6]
The heterocyclic amide compound or the salt thereof according to [5], in which X is
an oxygen atom;
Rla a hydrogen atom, a halogen atom, Ci^ alkyl, (Ci^) alkyl optionally substituted
with R6, C3_6 cycloalkyl, (C3^) cycloalkyl optionally substituted with R6, C2-6 alkenyl,
C2_6 alkynyl, C3^ cycloalkenyl, -C(0)R8, -OR9, -S(O)mlRi0, -N(Rn)R!2, -C(=NRi2b)R8b,
phenyl, phenyl substituted with (R7)p, U-5a, U-6a, U-7, U-8, U-10a, U-lla, U-12a, or
U-13a;
R2a is Ci_6 alkyl, Ci-e haloalkyl, or -S(0)ra3R20, and when n is an integer of 2 or more,
R2a are optionally the same as or different from each other;
R6 is a halogen atom, cyano, C3-6 cycloalkyl, -C(0)R8, -C(0)OR16, -OR13,
-S(0)m2R'4, or phenyl substituted with (R7)p; and
R27 is a halogen atom, phenyl, -OR29, or -S(0)m4R30.
[0012] [7]
The heterocyclic amide compound or the salt thereof according to [6], in which R4a
is a hydrogen atom, C1-6 alkyl, (Ci-e) alkyl optionally substituted with R27, or C3-6
cycloalkyl; and
R27 is a halogen atom or -OR29.
[0013] [8]
The heterocyclic amide compound or the salt thereof according to [4], in which Q is
an aromatic heterocycle of Q-3; and
W is an aromatic heterocycle of W-l.
[0014] [9]
The heterocyclic amide compound or the salt thereof according to [8], in which Rla
is a hydrogen atom, a halogen atom, Ci-e alkyl, (C1-6) alkyl optionally substituted with R6,
14
C3-6 cycloalkyl, (C3-6) cycloalkyl optionally substituted with R6, C2-6 alkenyl, C2-6 alkynyl,
-C(0)R8, -S(O)mlR]0, -N(Rn)R12, phenyl, phenyl substituted with (R7)P, U-3, U-5a, U-6a,
U-8,U~10a,orU-13a;
R2a is a halogen atom, Ci-e alkyl, or Ci-e haloalkyl, and when n is an integer of 2 or
5 more, R2a are optionally the same as or different from each other;
R6 is a halogen atom, -C(0)OR16, -OR13, -SCO^R14, or phenyl substituted with
(R7)P;
R7 is a halogen atom, C^ alkyl, or -OR15;
R8 is a hydrogen atom or Ci-6 alkyl;
10 ' R11 is Ci^ alkyl, (Ci_6) alkyl optionally substituted with R34, C3-6 cycloalkyl, C2-6
alkenyl, C2-6 alkynyl, phenyl, or phenyl substituted with (R7)p;
R11 optionally forms a 6-membered ring together with a nitrogen atom to which Rn
and R12 are bonded by forming a C5 alkylene chain together with R12, and in this case, the
alkylene chain optionally contains one O, S, S(O), or S(0)2;
15 R16
4is a hydrogen atom or C1-6 alkyl;
R27'is phenyl substituted with (R28)r, -OR29, -C(0)OR16, or -S(0)m4R30;
R28 is a halogen atom or C1-6 alkyl; and
R is a halogen atom, cyano, C3-6 cycloalkyl, -OR , -S(0)m6R , phenyl, phenyl
substituted with (R7)p, U-l, or U-8.
20 [0015] [10]
The heterocyclic amide compound or the salt thereof according to [9], in which R5a
is Ci-6 alkyl, (C1-6) alkyl optionally substituted with R27, or C2-6 alkenyl; and
R27is-OR29or-S(0)m4R30.
[0016] [11]
25 The heterocyclic amide compound or the salt thereof according to any one of [1] to
[10], in which X is an oxygen atom.
[0017] [12]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[10], in which X is a sulfur atom.
15
[0018] [13]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[12], in which R3 is a hydrogen atom.
[0019] [14]
5 The heterocyclic amide compound or the salt thereof according to any one of [1] to
[12], in which R is Ci-6 alkyl.
[0020] [15]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[14], in which R2a is CM haloalkyl.
10 ; [0021] [16]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[14], in which R2a is a halogen atom.
[0022] [17]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
15 [14], in which R2a is -S(0)ra3R2?; and
R20 is Ci.« alkyl. '
[0023] [18]
The heterocyclic amide compound or the salt thereof according to any one of [ 1 ] to
[14], in which R2a is trifluoromethyl.
20 [0024] [19]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[18], in which n is an integer of 1, 2, or 3.
[0025] [20]
The heterocyclic amide compound or the salt thereof according to any one of [1 ] to
25 [18], in which n is an integer of 1.
[0026] [21]
The heterocyclic amide compound or the salt thereof according to any one of [ 1 ] to
[20], in which Q is an aromatic heterocycle of Q-2; and
W is an aromatic heterocycle of W-l.
16
[0027] [22]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[20], in which Q is an aromatic heterocycle of Q-4; and
W is an aromatic heterocycle of W-l.
5 [0028] [23]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[20], in which Q is an aromatic heterocycle of Q-5; and
W is an aromatic heterocycle of W-l.
[0029] [24]
10 The heterocyclic amide compound or the salt thereof according to any one of [1] to
[20], in which Q is an aromatic heterocycle of Q-l; and
W is an aromatic heterocycle of W-2.
[0030] [25]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
15 [20], in which Q is an aromatic heterocycle of Q-2; and
W is an aromatic heterocycle of W-2.
[0031] [26]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[20], in which Q is an aromatic heterocycle of Q-3; and
20 W is an aromatic heterocycle of W-2.
[0032] [27]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[20], in which Q is an aromatic heterocycle of Q-4; and
W is an aromatic heterocycle of W-2.
25 [0033] [28]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[20], in which Q is an aromatic heterocycle of Q-5; and
W is an aromatic heterocycle of W-2.
[0034] [29]
17
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[20], in which Q is an aromatic heterocycle of Q-l; and
W is an aromatic heterocycle of W-3.
[0035] [30]
5 The heterocyclic amide compound or the salt thereof according to any one of [1] to
[20], in which Q is an aromatic heterocycle of Q-2; and
W is an aromatic heterocycle of W-3.
[0036] [31]
The heterocyclic amide compound or the salt thereof according to any one of [ 1 ] to
10" [20], in which Q is an aromatic heterocycle of Q-3; and
W is an aromatic heterocycle of W-3.
[0037] [32]
The heterocyclic amide compound or the salt thereof according to any one of [ 1 ] to
[20], in which Q is an aromatic heterocycle of Q-4; and
15 Wis an aromatic heterocycle of W-3. t
[0038] [33]
The heterocyclic amide compound or the salt thereof according to any one of [ 1 ] to
[20], in which Q is an aromatic heterocycle of Q-5; and
W is an aromatic heterocycle of W-3.
20 [0039] [34]
The heterocyclic amide compound or the salt thereof according to anyone of [l]to
[33], in which R4a is a hydrogen atom.
[0040] [35]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
25 [33], in which R4a is a hydrogen atom or Ci_6 alkyl.
[0041] [36]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[33], in which R4a is C^ alkyl.
[0042] [37]
18
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[33], in which R4a is Ci_3 alkyl.
[0043] [38]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
5 [33], in which R4a is methyl.
[0044] [39]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[33], in which R4a is ethyl.
[0045] [40]
10 : The heterocyclic amide compound or the salt thereof according to any one of [1] to
[33], in which R4a is C3-6 cycloalkyl.
[0046] [41]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[33], in which R4a is Ci_3 haloalkyl.
15 [0047] [42]
The heterocyclic amide compound or the salt thereof accordmg to any one of [ 1 ] to
[41], in which R5a is a hydrogen atom.
[0048] [43]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
20 [41], in which R5a is Ci-e alkyl.
[0049] [44]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[41], in which R5a is d-3 alkyl.
[0050] [45]
25 The heterocyclic amide compound or the salt thereof according to any one of [1] to
[41], in which R5a is methyl.
[0051] [46]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[41], in which R5a is ethyl.
19
[0052] [47]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[41], in which R5a is (Ci-6) alkyl optionally substituted with R27;
R27 is -OR29 or -S(0)m4R30;
5 R29 is Ci.6 alkyl; and
R30 is Ci^ alkyl.
[0053] [48]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[41], in which R5a is C2-6 alkenyl.
10 * [0054] [49]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[48], in which Ria is Ci^ alkyl, (Ci-e) alkyl optionally substituted with R6, C3-6 cycloalkyl,
(C3^) cycloalkyl optionally substituted with R6, C2-6 alkenyl, -CHO, -S(O)miRi0,
-N(Rn)R12, phenyl, phenyl substituted with (R7)p, U-3, U-5a, U-6a, U-7, U-8,
15 U-10a,U-lla, U-12a, or U-13a;
R6 is a halogen atom, cyano, C3-6 cycloalkyl, -C(0)OR16, -OR13, ~S(0)m2R14, phenyl,
or phenyl substituted with (R )p;
R8 is Ci_6 alkyl;
R10 is Ci^ alkyl, (Ci^),alkyl optionally substituted with R34, C3_6 cycloalkyl, or C2-6
20 alkenyl;
Rn is Ci^ alkyl, (Ci^) alkyl optionally substituted with R34, C3_6 cycloalkyl, C2-6
alkenyl, phenyl, phenyl substituted with (R7)P, or U-7;
R is a hydrogen atom or Ci-6 alkyl;
R optionally forms a 5-6-membered ring together with a nitrogen atom to which
25 R^andR" are bonded by forming a C4-5 alkylene chain together with R , and in this
case, the alkylene chain optionally contains one O, S, S(O), or S(0)2;
R13 is a hydrogen atom, C1-6 alkyl, or (C^) alkyl optionally substituted with R34;
R14 is Ci_6 alkyl or (Ci-e) alkyl optionally substituted with R34;
Ri6 is a hydrogen atom, Ci-e alkyl, or (Ci^) alkyl optionally substituted with R37;
20
and
R34 is cyano, C3-6 cycloalkyl, -C(0)R8, -C(0)OR16, -OR33, ~S(0)m6R33, orU-l.
[0055] [50]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
5 [48], in which Rla is Ci^ alkyl, C3.6 cycloalkyl, C2-6 alkenyl, or -CHO.
[0056] [51]
The heterocyclic amide compound or the salt thereof according to any one of [ 1 ] to
[48], in which Rl a is C^ alkyl or C3^ cycloalkyl.
[0057] [52]
10 The heterocyclic amide compound or the salt thereof according to any one of [ 1 ] to
[48], in which Rla is C^ alkyl.
[0058] [53]
The heterocyclic amide compound or the salt thereof according to any one of [ 1 ] to
[48], in which Rla is C3-6 cycloalkyl.
15 [0059] [54]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[48], in which RIa is (Ci^) alkyl optionally substituted with R6; and
R6 is a halogen atom.
[0060] [55]
20 The heterocyclic amide compound or the salt thereof according to any one of [1] to
[48], in which Rla is (C^) alkyl optionally substituted with R6; and
R is cyano.
[0061] [56]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
25 [48], in which Rla is (Cj,6) alkyl optionally substituted with R6; and
R6 is C3-6 cycloalkyl.
[0062] [57]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[48], in which Rla is (C]„6) alkyl optionally substituted with R6; and
21
R6 is -C(0)OR16.
[0063] [58]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[48], in which R3a is (Ci-e) alkyl optionally substituted with R6;
5 R6 is-OR13; and
R13 is Ci-6 alkyl.
[0064] [59]
The heterocyclic amide compound or the saltthereof according to anyone of [ l ] to
[48], in which Rla is (Cf_6) alkyl optionally substituted with R6;
10 ' R6 is -OR13;
R13 is (Ci-e) alkyl optionally substituted with R34;
R34 is -OR33; and
R33 is Cw alkyl
[0065] [60]
15 The heterocyclic amide compound or the saltthereof according to anyone of [1] to
[48], in which Rla is (Ci_6) alkyl optionally substituted with R6;
R6 is -SCO^R14;
R14 is Ci-6 alkyl or (Ci^) alkyl optionally substituted with R34;
R34 is a halogen atom or -OR33; and
20 R33 is Ci_6 alkyl.
[0066] [61]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[48], in which Rla is (d_6) alkyl optionally substituted with R6;
R6 is -SCOXnaR14;
25 R8 is Ci^ alkyl;
R14 is (CU6) alkyl optionally substituted with R34;
R16 is Ci-e alkyl;
R34 is cyano, C3-6 cycloalkyl, -C(0)R8, -C(0)ORi6, -OR33, or -S(0)m6R33; and
R33 is Ci^ alkyl.
22
[0067] [62]
The heterocyclic amide compound orthe salt thereof according to any one of [1] to
[48], in which Ria is (Ci_6) alkyl optionally substituted with R6;
R6 is-SCO)^1 4 ; and
5 R14 is C2-6 alkenyl, C2-6 haloalkenyl, C2-6 alkynyl, or C2-6 haloalkynyl.
[0068] [63]
The heterocyclic amide compound or the salt thereof according to anyone of [1] to
[48], in which Ria is (C3-6) cycloalkyl optionally substituted with R6; and
R6 is a halogen atom.
10 : [0069] [64]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[48], in which Rla is (C3.6) cycloalkyl optionally substituted with R&;
R6 is-OR13; and
R13 is Ci_6 alkyl.
15 [0070] [65]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[48], in which Rl a is -S(O)miR!0.
[0071] [66]
The heterocyclic amide compound or the salt thereof according to any one of [ 1 ] to
20 [48], in which Rla is -S(0)miR10;
Ri0 is C1-6 alkyl, (Ci^) alkyl optionally substituted with R34, C3-6 cycloalkyl, or C2-6
alkenyl;
R34 is a halogen atom, cyano, C3-6 cycloalkyl, -C(0)R8, -C(0)OR16, or -OR33;
R8 is C3.6 alkyl;
25 R16 is Ci* alkyl; and
R33isCi-6alkyl.
[0072] [67]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[48], in which Rla is -S(O)miR10
; and
23
R10 is C^ alkyl.
[0073] [68]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[48], in which R!a is -S(0)miR10; and
5 R10 is C3-6 cycloalkyl.
[0074] [69]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[48], in which Rla is -S(0)miR10; and
R10isC2-6alkenyl.
10 ; [0075] [70]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[48], in which Rla is -S(0)m!R10; and
R10isC2^alkynyl.
[0076] [71]
15 The heterocyclic amide compound or the salt thereof according to any one of [1] to
[48], in which Rla is -S(0)m!R10;
R10 is (Cj-e) alkyl optionally substituted with R34;and
R34 is a halogen atom.
[0077] [72]
20 The heterocyclic amide compound or the salt thereof according to any one of [ 1 ] to
[48], in which R!a is -S(O)miRi0;
R10 is (Ci-e) alkyl optionally substituted with R34; and
R34 is cyano.
[0078] [73]
25 The heterocyclic amide compound or the salt thereof according to any one of [1] to
[48], in which Rla is -S(0)miR10;
R10 is (C^) alkyl optionally substituted with R34; and
R3 is C3-6 cycloalkyl.
[0079] [74]
24
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[48], in which RIa is -S(0)miR10;
R10 is (Ci-e) alkyl optionally substituted with R34;
R34 is -C(0)R8 and -C(0)OR!6;
5 R8 is Ci^ alkyl; and
R16 is Ci^ alkyl.
[0080] [75]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[48], in which Rla is -S(0)miR10;
10 ; R10 is (Ci-e) alkyl optionally substituted with R34;
R34 is -OR33; and
R33 is Ci-6 alkyl.
[0081] [76]
The heterocyclic amide compound or the salt thereof according to any one of [ 1 ] to
15 [48], in which Rla is -S(0)miR,10
R10 is (Ci-e) alkyl optionally substituted with R34;
R34 is -S(0)m6R33; and
R33 is CM alkyl.
[0082] [77]
20 The heterocyclic amide compound or the salt thereof according to any one of [1] to
[48], in which Rla is -N(Rn)R12.
[0083] [78]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[48], in which Rla is -N(Rn)R12;
25 R11 is Ci-e alkyl;
R12 is a hydrogen atom or Ci-e alkyl.
[0084] [79]
The heterocyclic amide compound or the salt thereof according to anyone of [1] to
[48], in which Rla is -N(RU)R12;
25
Rn is (Ci-6) alkyl optionally substituted with R34, C3-6 cycloalkyl, or C2-e alkenyl;
R is a hydrogen atom or Ci^ alkyl;
R34 is a halogen atom, cyano, or -S(0)m6R33; and
R33 is d.6 alkyl.
5 [0085] [80]
The heterocyclic amide compound or the salt thereof according to any one of [ 1 ] to
[48], in which Rl a is -N(Rn)R12;
Rn is (C1.6) alkyl optionally substituted with R34;
R is a hydrogen atom or Ci^ alkyl;
10 • R34 is-OR33; and
R33 is Ci^ alkyl.
[0086] [81]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[48], in which Rla is -N(Rn)Ri2; and
15 R11 optionally forms a 5-6-membered ring together with a nitrogen atom to which
R11 and R12 are bonded by forming a C4-5 alkylene chain together with R12, and in this
case, the alkylene chain optionally contains one O, S, S(O), or S(0)2-
[0087] [82]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
20 [48], in which Rl a is a substituent of the following structure formulae:
- N x ^ ^N^J ^H^J ^H^J ^H^J
[0088] [83]
The heterocyclic amide compound or the salt thereof according to any one of [ 1 ] to
25 [48], in which R a is a substituent of the following structure formulae:
26
f-S f~S '/0 y—S"0 = «0
[0089] [84]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[48], in which Rla is phenyl or phenyl substituted with (R7)p.
5 [0090] [85]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[48], in which Rla is (Ci_6) alkyl optionally substituted with R6; and
R6 is phenyl or phenyl substituted with (R7)p.
[0091] [86]
10 The heterocyclic amide compound or the salt thereof according to any one of [1] to
[48], in which Rla is (d_6) alkyl optionally substituted with R6;
R6is-OR!3;
R13 is (Ci_6) alkyl optionally substituted with R34; and
R34 is phenyl or phenyl substituted with (R7)P.
15 [0092] [87]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[48], in which Rla is (Ci.6) alkyl optionally substituted with R6;
R'is-SCOW^4;
Ru is (Ci-e) alkyl optionally substituted with R34; and
20 R34 is phenyl or phenyl substituted with (R7)p.
[0093] [88]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[48], in which Rla is -S(0)miR10;
R10 is (Ci-e) alkyl optionally substituted with R34; and
25 R34 is phenyl or phenyl substituted with (R7)P.
[0094] [89]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
27
[48], in which Rla is -N(Rn)R12;
R11 is (Ci-e) alkyl optionally substituted with R34;
R12 is a hydrogen atom or Ci-e alkyl;
R34 is phenyl or phenyl substituted with (R7)p.
5 [0095] [90]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[48], in which Rla is -N(Rn)R12;
R11 is phenyl or phenyl substituted with (R7)p; and
R12 is a hydrogen atom or Ci-e alkyl.
10' [0096] [91]
The heterocyclic amide compound or the salt thereof according to any one of [84] to
[90], in which R7 is a halogen atom, Ci_6 alkyl, (Ci^) alkyl optionally substituted with R27
or -OR15;
R15 is Ci_6 alkyl;
15 R27 is a halogen atom, -OR29, or -S(0)m4R30; and
R29andR30 are each independently Ci-6 alkyl.
[0097] [92]
The heterocyclic amide compound or the salt thereof according to any one of [84] to
[90], in which R7 is a halogen atom, Ci-6 alkyl, (Ci-e) alkyl optionally substituted with R27,
20 or -OR15;
R15 is Ci.6 alkyl; and
R27 is a halogen atom.
[0098] [93]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
25 [48], in which R a is any one of heterocycles of U-l to U-25.
[0099] [94]
The heterocyclic amide compound or the salt thereof according to any one of [ 1 ] to
[48], in which Rla is U-3, U-5a, U-6a, U-7, U-8, U-lOa, U-l la, U-12a, or U-l 3a.
[0100] [95]
28
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[48], in which Rla is -N(Rn)R12; and
R11 is U-7, U-8, U-9, or U-14 to U-19; and
R12 is a hydrogen atom or Cj-6 alkyl.
5 [0101] [96]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[48], in which Rla is -N(Rn)R12;
R11 is U-7; and
R12 is a hydrogen atom or Cj.6 alkyl.
10 [0102] [97]
The heterocyclic amide compound or the salt thereof accordmg to any one of [1] to
[48], in which Ria is -S(0)m3R10;
R10 is (Ci_6) alkyl optionally substituted with R34; and
R34 is U-7, U-8, U-9, or U-14 to U-19.
15 [0103] [98]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[48], in which Rla is -S(0)m]R10;
Ri0 is (Ci-e) alkyl optionally substituted with R34; and
R34 is U-l, U-3, or U-20 to U-25.
20 [0104] [99]
The heterocyclic amide compound or the salt thereof according to any one of [ 1 ] to
[48], in which Rla is -S(O)mlRi0;
Rso is (Ci-e) alkyl optionally substituted with R34; and
R34isU-l,U-3,orU-22a.
25 [0105] [100]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[48], in which RIa is -N(Rn)R12;
R11 is (Ci-e) alkyl optionally substituted with R34;
R12 is a hydrogen atom or Ci^ alkyl; and
29
R34 is U-7, U-8, U-9, or U-14 to U-19.
[0106] [101]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[48], in which Rla is -N(R1!)R12;
5 Ru is (Ci-e) alkyl optionally substituted with R34;
R12 is a hydrogen atom or Ci-6 alkyl; and
R34 is U-l, U-3, or U-20 to U-25.
[0107] [102]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
10 * [48], in which Rla is -N(Rn)R12;
R11 is (Ci-e) alkyl optionally substituted with R34;
R12 is a hydrogen atom or Ci-e alkyl; and
R34isU-l,U~3,orU-22a.
[0108] [103]
15 The heterocyclic amide compound or the salt thereof according to anyone of [ l ] to
[48], in which Rla is (Ci_6) alkyl optionally substituted with R6;
R6is-OR13;
R13 is (Ci-e) alkyl optionally substituted with R34; and
R34 is U-7, U-8, U-9, or U-14 to U-19.
20 [0109] [104]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[48], in which Rla is (Ci_6) alkyl optionally substituted with R6;
R6is-OR13;
Ri3 is (Ci-6) alkyl optionally substituted with R34; and
25 R34 is U-l, U-3, or U-20 to U-25.
[0110] [105]
The heterocyclic amide compound or the salt thereof according to any one of [1] to
[48], in which RIa is (Ci^) alkyl optionally substituted with R6;
R6is-QR13;
30
R13 is (Ci^) alkyl optionally substituted with R34; and
R34isU-l,U-3,orU-22a.
[0111] [106]
The heterocyclic amide compound or the salt thereof according to any one of [ 1 ] to
5 [48], in which Ria is (Ci-e) alkyl optionally substituted with R6;
R'Ms-SCCTWR14;
R14 is (Ci-e) alkyl optionally substituted with R34; and
R34 is U-7, U-8, U-9, or U-14 to U-19.
[0112] [107]
10 The heterocyclic amide compound or the salt thereof according to any one of [1] to
[48], in which Rla is (Cj.6) alkyl optionally substituted with R6;
R'is-SCO^R14;
R14 is (Ci-e) alkyl optionally substituted with R34; and
R34 is U-l, U-3, or U-20 to U-25.
15 [0113] [108]
The heterocyclic amide compound or the salt thereof according to anyone of [1] to
[48], in which Rla is (Ci_6) alkyl optionally substituted with R6;
R^s-SCO^R14;
R14 is (Ci-6) alkyl optionally substituted with R34; and
20 R34isU-l,U-3,orU-22a.
[0114] [109]
The heterocyclic amide compound or the salt thereof according to any one of [93] to
[108], in which tl, t2, t3, t4, t5, t7, t8, and t9 are each independently an integer of 0.
[0115] [110]
25 The heterocyclic amide compound or the salt thereof according to any one of [93] to
[108], in which R is a halogen atom, cyano, Ci-e alkyl, Ci-e haloalkyl, C3..6 cycloalkyl,
(Ci-e alkoxy) Cue alkyl, -OR31, or -S(0)m4R3°.
[0116] [111]
The heterocyclic amide compound or the salt thereof according to any one of [93] to
31
[108], in which R28 is a halogen atom.
[0117] [112]
The heterocyclic amide compound or the salt thereof according to any one of [93] to
[108], in which R28 is Ci-e alkyl.
5 [0118] [113]
The heterocyclic amide compound or the salt thereof according to any one of [93] to
[108], in which R28 is d-e alkoxy.
[0119] [114]
An agricultural chemical comprising one or two or more of compounds selected
10 from the heterocyclic amide compound and the salt thereof as described in any one of [1]
to [113] as an active component.
[0120] [115]
A herbicide comprising one or two or more of compounds selected from the
heterocyclic amide compound and the salt thereof as described in any one of [1] to [113]
15 as an active component.
Effects of the Invention
[0121] The compound of the present invention has excellent herbicidal activity to
various weeds and has a high level of safety to the target crops. In addition, the
compound of the present invention has almost no adverse effect on non-target creatures
20 such as mammals, fish, and beneficial insects and has light environmental burden due to
low residual properties.
Accordingly, the present invention can provide a useiul herbicide in the agricultural
and horticultural fields such as paddy fields, dry fields, and orchards.
25 MODES FOR CARRYING OUT THE INVENTION
[0122] The compounds included in the present invention may include the
geometric isomers of an E-form and a Z-form depending on the substituents. The
present invention includes the E-form, the Z-form, and a mixture of the E-form and the
32
Z-form in any ratios. The compounds included in the present invention include
optically active isomers due to the existence of one or two or more of asymmetric carbon
atoms. The present invention includes all optically active isomers or racemic forms.
[0123] The compounds included in the present invention may include tautomers
depending on the substituents. The present invention includes all tautomers or a mixture
of the tautomers included in any ratios. For example, in the case of the compound of
Formula (1): [where W is W-1; Rla is hydroxy group; n, Q, R2a, R3, and X mean the same
as described above], the following tautomers are included.
10
X NQ
- N ^ N ^ ° H X i
3 K^ 3
n
[01£4] Similarly, in the case of the compound of Formula (1):
,1a 2a
2a
n
[where W is W-1; R is -SH group; n, Q, R , R , and X mean the same as described
above], the following tautomers are included.
Q-
*£.
15
[0125] Among the compounds included in the present invention, the compounds
that can form acid-added salt by a conventional method may form, for example, the salts
of hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, and
hydroiodic acid; the salts of inorganic acids such as nitric acid, sulfuric acid, phosphoric
20 acid, chloric acid, and perchloric acid; the salts of sulfonic acids such as methanesulfonic
acid, ethanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid, and
33
p-toluenesulfonic acid; the salts of carboxylic acids such as formic acid, acetic acid,
propionic acid, trifluoroacetic 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 glutamic acid and aspartic acid.
5 [0126] Among the compounds included in the present invention, the compounds
that can form 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.
Specific examples of each substituent described in this specification will be
10 ; described below. Here, n- means normal; i- means iso; s- means secondary; and tertmeans
tertiary and Ph means phenyl.
[0127] Examples of the halogen atom in this specification may include a fluorine
atom, a chlorine atom, a bromine atom, and an iodine atom. The expression of "halo" in
this specification is also these halogen atoms.
15 The expression of Ca-b all^yl in this specification is a linear or a branched
hydrocarbon group having a carbon atom number 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, n-pentyl group, 1,1-dimethyl propyl
group, n-hexyl group and the like. Each of these groups is selected in a range of the
20 specified carbon atom number.
[0128] The expression of Ca.b cycloalkyl in this specification is a cyclic
hydrocarbon group having a carbon atom number 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 may be optionally substituted with an alkyl group in a range of the specified carbon
25 atom number. Specific example of the Ca-b cycloaJkyl may include cyclopropyl group,
1-methylcyclopropyl group, 2-methylcyclopropyl group, 2,2-dimethylcyclopropyi group,
cyclobutyl group, cyclopentyl group, cyclohexyl group and the like. Each of these
groups is selected in a range of the specified carbon atom number.
[0129] The expression c f Ca„b halo cycloalkyl in this specification is a cyclic
34
hydrocarbon group having a carbon atom number of a to b in which the hydrogen atom
bonded to the carbon atom is optionally substituted with a halogen atom and can form a
monocyclic structure or a fused ring structure of a 3-membered ring to a 10-membered
ring. Each ring can be optionally substituted with an alkyl group in a range of the
5 specified carbon atom number. 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 two or
more halogen atoms are used as substituents, these halogen atoms are optionally the same
as or different from each other. Specific examples of the Ca-b halocycloalkyl may
include 2,2-difiuorocyclopropyl group, 2,2-dichlorocyclopropyl group,
10 •' 2,2-dibromocyclopropyl group, 2,2-difluoro-1 -methylcyclopropyl group,
2,2-dichloro-l-methylcyclopropyl group, 2,2-dibromo-l-methylcyclopropyl group,
2,2,3,3-tetra-fluorocyclobutyl group and the like. Each of these groups is selected in a
range of the specified carbon atom number.
[0130] The expression of Ca-b alkenyl in this specification is a linear or a
15 branched unsaturated hydrocarbon group having a carbon atom number of a to b and
having one or two or more double bonds in the molecule. Specific examples of the Ca-b
alkenyl may include vinyl group, 1-propenyl group, 2-propenyl group, 1-methylethenyl
group, 2-butenyl group, 2-methyl-2-propenyl group, 3-methyl-2-butenyl group,
l,l-dimethyl-2-propenyl group and the like. Each of these groups is selected in a range
20 of the specified carbon atom number.
[0131] The expression of Ca„b haloalkenyl in this specification is a linear or a
branched unsaturated hydrocarbon group having a carbon atom number of a to b in which
the hydrogen atom bonded to the carbon atom is optionally substituted with a halogen
atom and having one or two or more double bonds in the molecule. In this case, when
25 two or more halogen atoms are used as substituents, these halogen atoms are optionally
the same as or different from each other. Specific examples of the Ca-b haloalkenyl may
include 2,2-dichlorovinyl group, 2-fluoro-2-propenyl group, 2-chloro-2-propenyl group,
3-chloro-2-propenyl group, 2-bromo-2-propenyl group, 3,3-difluoro-2-propenyl group,
2,3-dichloro-2-propenyl, 3,3-dichloro-2-propenyl group, 2,3,3-trifluoro-2-propenyl group,
35
2,3,3-trichloro-2~propenyl group, l-(trifluoromethyl) ethenyl group,
4,4-difluoro-3-butenyl group, 3,4,4-trifluoro-3-butenyl group,
3-chloro-4,4,4-trifluoro-2-butenyl group and the like. Each of these groups is selected
in a range of the specified carbon atom number.
5 [0132] The expression of Ca-b cycloalkenyl in this specification is a cyclic
unsaturated hydrocarbon group having a carbon atom number of a to b and having one or
two 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 substituted with an alkyl
group in a range of the specified carbon atom number. The double bond may be either
10 - endo-form or exo-form. Specific example of the Ca-b cycloalkenyl may include
1-cyclopentene-l-yl group, 2-cyclopentene-l-yl group, 1-cyclohexen-l-yl group,
2-cyclohexen-l-yl group and the like. Each of these groups is selected in a range of the
specified carbon atom number.
[0133] The expression of Ca-b alkynyl in this specification is a linear or a
15 branched unsaturated hydrocarbon group having a carbon atom number of a to b and
having one or two or more triple bonds in the molecule. Specific examples of the Ca_b
alkynyl may include ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl
group, 2-butynyl group, 3-butynyl group, l,l-dimethyl-2-propynyl group and the like.
Each of these groups is selected in a range of the specified carbon atom number.
20 [0134] The expression of Ca_b haioalkynyl in this specification is a linear or a
branched unsaturated hydrocarbon group having a carbon atom number of a to b in which
the hydrogen atom bonded to the carbon atom is optionally substituted with a halogen
atom and having one or two or more triple bonds in the molecule. In this case, when
two or more halogen atoms are used as substituents, these halogen atoms are optionally
25 the same as or different from each other. Specific examples of the Ca-b haioalkynyl may
include 2-chloroethynyI group, 2~bromoethynyl group, 2-iodoethynyl group,
3-chloro-2-propynyl group, 3-bromo-2-propynyl group, 3-iodo-2-propynyl group and the
like. Each of these groups is selected in a range of the specified carbon atom number.
[0135] The expression of Ca-b haloalkyl in this specification is a linear or a
36
branched hydrocarbon group having a carbon atom number of a to b in which the
hydrogen atom bonded to the carbon atom is optionally substituted with a halogen atom.
When two or more halogen atoms are used as substituents, these halogen atoms are
optionally the same as or different from each other. Specific examples of the Ca-b
5 haloaikyl may include fluoromethyl group, chloromethyl group, bromomethyl group,
iodomethyl group, difluoromethyl group, dichloromethyl group, a trifluoromethyl group,
chlorodifluoromethyl group, trichloro methyl group, bromodifluoromethyl group,
2-fluoroethyl group, 2-chloroethyl group, 2-bromoethyl group, 2,2-difluoroethyl group,
2,2,2-trifluoroethyl group, 2-chloro-2,2-difluoroethyl group, 2,2,2-trichloroethyl group,
10 1,1,2,2-tetrafluoroethyl group, 2-chloro-l,l,2-trifluoroethyl group, pentafluoroethyl
group, 3,3,3-trifluoropropyl 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-(trifluoromethyI)ethyl group,
2,2,3,3,4,4,4-heptafluorobutyl group, nonafluorobutyl group and the like. Each of these
15 groups is selected in a range of the specified carbon atom number.
[0136] The expression of Ca-b alkoxy in this specification is an alkyl-O- group in
which this alkyl is the above meaning alkyl group having a carbon atom number of a to b.
Specific examples of the Ca-b alkoxy may include methoxy group, ethoxy group,
n-propyloxy group, i-propyloxy group, n-butyloxy group, i-butyloxy group, s-butyloxy
20 group, tert-butyloxy group and the like. Each of these groups is selected in a range of
the specified carbon atom number.
[0137] The expression of Ca-b alkylthio in this specification is an alkyl-S- group
in which this alkyl is the above meaning alkyl group having a carbon atom number of a to
b. Specific examples of the Ca-b alkylthio may include methylthio group, ethylthio
25 group, n-propylthio group, i-propylthio group, n-butylthio group, i-butylthio group,
s-butylthio group, tert-butylthio group and the like. Each of these groups is selected in a
range of the specified carbon atom number.
[0138] The expression of Ca_b alkylcarbonyl in this specification is an alkyl-C(O)-
group in which this alkyl is the above meaning alkyl group having a carbon atom number
37
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, heptanoyl group and the like.
Each of these groups is selected in a range of the specified carbon atom number.
5 [0139] The expression of Ca_b halo alkylcarbonyl in this specification is a
halo alky l-C(O)- group in which this haloalkyl is the above meaning haloalkyl group
having a carbon atom number of a to b. Specific examples of the Ca-b halo alkylcarbonyl
may include fluoroacetyl group, chloroacetyl group, difluoroacetyl group, dichloroacetyl
group, trifluoroacetyl group, chlorodifluoro acetyl group, bromodifluoroacetyl group,
10 - trichloroacetyl group, pentafluoropropionyl group, heptafluorobutanoyl group,
3-chloro~2,2-dimethylpropanoyl group and the like. Each of these groups is selected in
a range of the specified carbon atom number.
[0140] The expression of Ca-b cycloalkylcarbonyl in this specification is a
cycloalkyl-C(O)- group in which this cycloalkyl is the above meaning cycloalkyl group
15 having a carbon atom number of a to b. Specific examples of the Ca-b
cycloalkylcarbonyl may include cyclopropylcarbonyl group,
2-methylcyclopropylcarbonyl group, cyclobutylcarbonyl group and the like. Each of
these groups is selected in a range of the specified carbon atom number.
[0141] The expression of Ca-b halo cyclo alkylcarbonyl in this specification is a
20 halocycloalkyl-C(O)- group in which this halocycloalkyl is the above meaning
halocycloalkyl having a carbon atom number of a to b. Specific examples of the Ca-b
halocycloalkylcarbonyl may include 2,2-dichloro cyclopropylcarbonyl group,
2,2-dichloro-l-methylcyclopropylcarbonyl group and the like. Each of these groups is
selected in a range of the specified carbon atom number.
25 [0142] The expression of Ca-b alkoxycarbonyl in this specification is an
alkyl-O-C(O)- group in which this alkyl is the above meaning alkyl having a carbon atom
number 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,
38
tert-butoxycarbonyl group and the like. Each of these groups is selected in a range of
the specified carbon atom number.
[0143] The expression of Ca-b haloalkoxycarbonyl in this specification is a
haloalkyl-O-C(O)- group in which this haloalkyl is the above meaning haloalkyl group
5 having a carbon atom number of a to b. Specific examples of the Ca-b
haloalkoxycarbonyl may include chloromethoxycarbonyl group, 2-chloroethoxycarbonyi
group, 2,2-difluoroethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group,
2,2,2-trichloroethoxycarbonyl group and the like. Each of these groups is selected in a
range of the specified carbon atom number.
104 [0144] The expression of Ca-b alkylaminocarbonyl in this specification is a
carbamoyl group in which one hydrogen atom is substituted with the above meaning
alkyl group having a carbon atom number of a to b. Specific examples of the Ca_b
alkylaminocarbonyl may include methylcarbamoyl group, ethylcarbamoyl group,
n-propylcarbamoyl group, i-propylcarbamoyl group, n-butylcarbamoyl group,
15 i-butylcarbamoyl group, s~butylcarbamoyl group, tert-butylcarbamoyl group and the like.
Each of these groups is selected in a range of the specified carbon atom number.
[0145] The expression of Ca_b haloalkylaminocarbonyl in this specification is a
carbamoyl group in which one hydrogen atom is substituted with the above meaning
haloalkyl group having a carbon atom number of a to b. Specific examples of the Ca-b
20 haloalkylaminocarbonyl may include 2-fluoroethylcarbamoyl group,
2-chloroethylcarbamoyl group, 2,2-difluoro ethylcarbamoyl group,
2,2,2-trifluoroethylcarbamoyl group and the like. Each of these groups is selected in a
range of the specified carbon atom number.
[0146] The expression of di(Ca-b alkylaminocarbonyl in this specification is a
25 carbamoyl group in which both hydrogen atoms are substituted with the above meaning
alkyl groups, which are the same as or different from each other, having a carbon atom
number of a to b. Specific examples of the di(Ca-b alkylaminocarbonyl may include
N,N-dimethylcarbamoyl group, N-ethyl-N-methylcarbamoyl group,
N,N-diethylcarbamoyl group, N,N-di(n-propyl)carbamoyl group,
39
N,N-di(n-butyl)carbamoyl group and the like. Each of these groups is selected in a
range of the specified carbon atom number.
[0147] The expression of Ca-b alkylaminosulfonyl in this specification is a
sulfamoyl group in which one hydrogen atom is substituted with the above meaning alkyl
5 group having a carbon atom number of a to b. Specific examples of the Ca-b
alkylaminosulfonyl may include methylsulfamoyl group, ethylsulfamoyl group,
n-propylsulfamoyl group, i-propylsulfamoyl group, n-butylsulfamoyl group,
i-butylsulfamoyl group, s-butylsulfamoyl group, tert-butylsulfamoyl group and the like.
Each of these groups is selected in a range of the specified carbon atom number.
10 [0148] The expression of di(Ca-b alkyl)aminosulfonyl in this specification is a
sulfamoyl group in which both hydrogen atoms are substituted with the above meaning
alkyl groups, which are the same as or different from each other, having a carbon atom
number of a to b. Specific examples of the di(Ca-b alkylaminosulfonyl may include
N,N-dimethylsulfamoyl group, N-ethyl-N~methylsulfarnoyl group, N,N-diethylsulfamoyl
15 group, N,N-di(n-propyl)sulfarnoyl group, N,N-di(n-butyl)sulfamoyl group and the like.
Each of these groups is selected in a range of the specified carbon atom number.
[0149] The expression of Ca-b alkylamino in this specification is an amino group
in which one hydrogen atom is substituted with the above meaning alkyl group having a
carbon atom number of a to,b. Specific examples of the Ca-b alkylamino may include
20 methylamino group, ethylamino group, n-propylamino group, i-propylamino group,
n-butylamino group, i-butylamino group, tert-butylamino group and the like. Each of
these groups is selected in a range of the specified carbon atom number.
[0150] The expression of di(Ca-b alkyl)amino in this specification is an amino
group in which both hydrogen atoms are substituted with the above meaning alkyl groups,
25 which are the same as or different from each other, having a carbon atom number of a to
b. Specific examples of the di(Ca-b a1kyl)amino may include dimethylamino group,
ethyl(methyl)ammo group, diethylamino group, n-propyl(methyl)amino group,
i-propyl(methyl)amino group, di(n-propyl)amino group, di(n-butyl)amino group and the
like. Each of these groups is selected in a range of the specified carbon atom number.
40
[0151] The expression of (Ca_b) alkyl optionally substituted with R6, (Ca_b) alkyl
optionally substituted with R27, (Ca-b) alkyl optionally substituted with R34, (Ca.b) alkyl
optionally substituted with R35, or (Ca-b) alkyl optionally substituted with R36 in this
specification is the above meaning alkyl group having a carbon atom number of a to b in
5 which the hydrogen atoms bonded to the carbon atoms are optionally substituted with any
R°, Rz/, R , W\ or R". Each of these groups is selected in a range of the specified
carbon atom number. In this case, when two or more of substituents R6, R27, R34, R35, or
R36 are contained in the (Ca.b) alkyl group, R6, R27, R34, R35, or R36 are optionally the
same as or different from each other.
10 " [0152] The expression of (Ca-b) cycloalkyl optionally substituted with R6 or (Ca-b)
cycloalkyl optionally substituted with R27 in this specification is the above meaning
cycloalkyl group having a carbon atom number of a to b in which the hydrogen atoms
bonded to the carbon atoms are optionally substituted with any R6 or R27. Each of these
groups is selected in a range of the specified carbon atom number. In this case, when
15 two or more of substituents R6 or R27 are contained in the (Ca„b) cycloalkyl group, R6 or
R are optionally 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.
[0153] Specific examples of the expression of "Ru optionally forms a
3-7-membered ring together, with a nitrogen atom to which R! and R12 are bonded by
20 forming a C2-6 alkylene chain together with R , and in this case, the alkylene chain
optionally contains one O, S, S(O), S(0)2, or N(R33) and is optionally substituted with an
oxo group or a thioxo group", "Rlia optionally forms a 3-7-membered ring together with a
nitrogen atom to which Rl l a and R12a are bonded by forming a C2-6 alkylene chain
together with R12a, and in this case, the alkylene chain optionally contains one O, S, S(O),
25 S(0)2, or N(R33) and is optionally substituted with an oxo group or a thioxo group", and
"R21 optionally forms a 3-7-membered ring together with a nitrogen atom to which R2i
and R22 are bonded by forming a C2-6 alkylene chain together with R22, in this case, the
alkylene chain optionally contains one O, S, S(O), S(0)2, or N(R39) and is optionally
substituted with an oxo group or a thioxo group" in this specification may include
41
aziridine, azetidine, azetidin-2-one, pyrrolidin, pyrrolidin-2-one, oxazolidine,
oxazolidin-2-one, oxazolidin-2-thione, ttriazolidine, thiazolidin-2-one,
thiazolidin~2-thione, imidazolidine, imidazolidin-2-one, imidazolidin-2-thione, piperidine,
piperidin-2-one, piperidin-2-thione, 2H-3,4,5,6-tetrahydro-l,3-oxazin-2-one,
5 2H-3,4,5,6-tetrahydro-l,3-oxazme-2-thione, morpholine,
2H-3,4,5,6-tetrahydro-l,3-thiazin-2-one, 2H-3,4,5,6-tetrahydro-l,3-thiazin-2-thione,
thiomorpholine, thiomorpholine-1-oxide, thiomorpholine-l,l-dioxide,
perhydropyrimidin-2-one, piperazine, homopiperidine, homopiperidin-2-one,
heptamethyleneimine and the like. Each of these groups is selected in a range of the
10 * specified carbon atom number.
[0154] The expression of (Ca~b alkoxy) Cd-ealkyl, (Ca-b alkylthio) Cd-ealkyl, or the
like in this specification is a linear or a branched hydrocarbon group having a carbon
atom number of d to e in which the hydrogen atom bonded to the carbon atom is
optionally substituted with the any above meaning Ca-b alkoxy group or Ca-b alkylthio
15 group respectively. Each of these groups is selected in a range of the specified carbon
atom number.
[0155] The "5-6-membered aromatic heterocycle" in this specification means a
monocyclic aromatic heterocycle in which the number of atoms forming the ring is 5 to 6
and 1 to 5 hetero atoms (the, hetero atom means a nitrogen atom, an oxygen atom, or a
20 sulfur atom) are contained in the atoms formmg the ring. Specific examples of the
5-6-membered aromatic heterocycle may include pyrrole, pyrazole, imidazole, triazole,
tetrazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, furan, thiophene, thiazole,
isothiazole, oxazole, isoxazole, oxadiazole, thiadiazole and the like.
When the "5-6-membered aromatic heterocycle" contains a C=N double bond, the
25 nitrogen atom may be N-oxide.
[0156] The "5-6-membered heteroaryl" in this specification means a monovalent
substituent formed by removing one hydrogen atom from any position in the above
meaning "5-6-membered aromatic heterocycle". Positions to which these substituents
are bonded are mot particularly limited and the substituents may be bonded to desired
42
positions.
[0157] The "3-7-membered non-aromatic heterocycle" in this specification means
a monocyclic non-aromatic heterocycle having the following characteristics:
1) the number of atoms forming the ring is 3 to 7,
5 2) 1 to 3 hetero atoms (the hetero atom means a nitrogen atom, an oxygen atom, or a
sulfur atom) are contained in the atoms forming the ring,
3) a carbonyl group, a thiocarbonyl group, a double bond, or a triple bond may be
contained in the ring, and
4) when a sulfur atom is contained in the atoms forming the ring, the sulfur atom
10 may be a sulfinyl group or a sulfonyl group.
Specific examples of the 3-7-membered non-aromatic heterocycle may include
azetidine, pyrrolidine, pyrrolidinone, oxazolidine, isoxazolidine, thiazolidine,
isothiazolidine, piperazine, piperazinone, piperidine, piperidinone, morpholine,
thiomorpholine, azepine, diazepine, oxetane, tetrahydroforan, 1,3-dioxolane,
15 tetrahydropyran, 1,4-dioxane, oxepane, homomorpholine and the like.
[0158] The "3-7-membered heterocyclyl" in this specification means a
monovalent substituent formed by removing one hydrogen atom from any position in the
above meaning "3-7-membered non-aromatic heterocycle". Positions to which these
substituents are bonded are not particularly limited and the substituents may be bonded to
20 desired positions.
[0159] The "5-6-membered heteroaryl optionally substituted with R28 and R28a" in
this specification is a "5-6-membered heteroaryl" in which the hydrogen atoms on the
carbon atoms forming the ring of the "5-6-membered heteroaryl" are substituted on the
carbon atoms with any R28 in a range of the number of the existing hydrogen atoms. In
25 this case, when nitrogen exists among the atoms forming the ring of the "5-6-membered
heteroaryl" and the nitrogen atom potentially has aNH structure, the "5-6-membered
heteroaryl optionally substituted with R28 and R28a" is a "5-6-membered heteroaryl" in
which the hydrogen atom on the nitrogen atom is optionally substituted on the nitrogen
atom with any R in a range of the number of existing hydrogen atoms. In this case,
43
when two or more substituents R on the carbon atoms forming the ring of the
"5-6-membered heteroaryl" and two or more substituents R28a substituted with the
nitrogen atom potentially having a NH structure forming the ring independently exist,
two or more of each of R28 and R28a are optionally the same as or different from each
5 other, and when two R28 are adjacent, the two adjacent R28 optionally form a 6-membered
ring together with carbon atoms to which each R28 is bonded by forming
-CH=CH-CH=CH~.
[0160] The "3-7-membered heterocyclyl optionally substituted with R28 and R28a"
in this specification is a "3-7-membered heterocyclyl" in which the hydrogen atoms on
10 the carbon atoms forming the ring of the "3-7-membered heterocyclyl" are substituted on
the carbon atoms with any R28 in a range of the number of the existing hydrogen atoms.
In this case, when nitrogen exists among the atoms forming the ring of the
"3-7-membered heterocyclyl" and the nitrogen atom potentially has a NH structure, the
"3-7-membered heterocyclyl optionally substituted with R28a" is a "3-7-membered
15 heterocyclyl" in which the hydrogen atom on the nitrogen ajtom is optionally substituted
on the nitrogen atom with any R in a range of the number of existing hydrogen atoms.
TO
In this case, when two or more substituents R on the carbon atoms forming the ring of
the "3-7-membered heterocyclyl" and two or more substituents R28a substituted with the
nitrogen atom potentially having a NH structure forming the ring independently exist,
20 two or more ofeachofR28andR28a are optionally the same as or different from each
other, and when two R28 are adjacent, the two adjacent R28 optionally form a 6-membered
ring together with carbon atoms to which each R28 is bonded by forming
-CH=CH-CH=CH~.
[0161] Next, the production method of the compound of the present invention
25 will be described below.
Production method A
The heterocyclic amide compound of Formula (1) can be produced by, for example,
reacting the compound of Formula (2) with the compound of Formula (3a).
44
•3 HC
(2) (
.3 [0162] The compound of Formula (1): [where Q and R , W, and X mean the
same as defined above] of the present invention can be produced by reacting the
compound of Formula (2): [where Q and R3 mean the same as defined above] or the salt
5 h thereof with the compound of Formula (3a): [where W and X mean the same as defined
above] or the salt thereof in a solvent or without using a solvent by using a base, a
condensing agent, and/or a catalyst if necessary and adding an additive if necessary.
In this reaction, the compound of Formula (3a) can be used in a range of 0.1
equivalents to 100 equivalents relative to 1 equivalent of the compound of Formula (2).
10 [0163] When the solvent is used, the solvent to be used may be a solvenf that is
inactive to the reaction. Example of the solvent may include polar solvents such as
N,N-dirnethylformamide, N,N-dimethylacetamide, acetonitrile, dimethylsulfoxide, and
l,3-dimethyl-2-imidazolinone; ethers such as diethyl ether, tetrahydrofuran, 1,4-dioxane,
1,2-dimethoxyethane, and djphenyl ether; aromatic hydrocarbons such as benzene,
15 toluene, and xylene; halogenated hydrocarbons such as methylene chloride, chloroform,
carbon tetrachloride, and 1,2-dichloroethane; and aliphatic hydrocarbons such as
n-pentane and n-hexane. These solvents may be used singly or in combination of two or
more of them.
[0164] When the base is used, examples of the base to be used may include
20 organic bases such as triethylamine, pyridine, and 4-(dimethylamino)pyridine and
inorganic bases such as potassium carbonate and sodium carbonate. These bases may
be used in a range of 0.1 equivalents to 50 equivalents relative to 1 equivalent of the
compound of Formula (2).
[0165] When the condensing agent is used, examples of the condensing dgent to
45
be used may include lH-benzotriazol-l-yloxytris(dimethylamino)phosphonmm
hexafluorophosphate, N,N'-dicyclohexylcarbodiimide,
l-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, and
2-chloro-l-methylpyridinium iodide. These condensing agents may be used in a range
5 of 0.1 equivalents to 50 equivalents relative to 1 equivalent of the compound of Formula
(2).
[0166] When the additive is used, examples of the additive to be used may
include 3H-[l,2,3]triazolo[4,5-b]pyridine-3-oi and 1-hydroxybenzotriazole. These
additives may be used in a range of 0.1 equivalents to 50 equivalents relative to 1
10 equivalent of the compound of Formula (2).
[0167] As the reaction temperature, any temperature from -78°C to the reflux
temperature of the reaction mixture can be set. Although the reaction time varies
depending on the concentration of the reaction substrate and the reaction temperature,
usually any time may be set in a range of 5 minutes to 100 hours.
15 Some of the compounds of Formula (2) are known compounds and some of the
compounds are commercially available.
Some of the compounds of Formula (3a) are known compounds and can be
synthesized in accordance with known methods described in documents. Examples of
the methods known in the documents may include a method described in WO
20 2008/006540 Pamphlet.
[0168] Production method B
The heterocyclic amide compound of Formula (1) can be produced by, for example,
reacting the compound of Formula (2) with the compound of Formula (3b).
46
3
[0169] The compound of Formula (1): [where Q and R , W, and X mean the
same as defined above] of the present invention can be produced by reacting the
compound of Formula (2): [where Q and R3 mean the same as defined above] or the salt
5 thereof with the compound of Formula (3b): [where W and X mean the same as defined
above and Xa is a leaving group such as a halogen atom] or the salt thereof in a solvent or
without using a solvent by using a base if necessary.
In this reaction, the compound of Formula (3b) can be used in a range of 0.1
equivalents to 100 equivalents relative to 1 equivalent of the compound of Formula (2).
10 [0170] When the solvent is used, the solvent to be used may be a solvent that is
inactive to the reaction. Example of the solvent may include polar solvents such as
N,N-dimethylformamide, N,N-dimethylacetamide, acetonitrile, dimethylsulfoxide, and
l,3-dimethyl~2-imidazolmone; ethers such as diethyl ether, tetrahydrofiiran, 1,4-dioxane,
1,2-dimethoxyethane, and djphenyl ether; aromatic hydrocarbons such as benzene,
15 toluene, and xylene; halogenated hydrocarbons such as methylene chloride, chloroform,
carbon tetrachloride, and 1,2-dichloroethane; and aliphatic hydrocarbons such as
n-pentane and n-hexane. These solvents may be used singly or in combination of two or
more of them.
[0171] When the base is used, examples of the base to be used may include
20 organic bases such as triethylamine, pyridine, and 4-(dimethylamino)pyridine and
inorganic bases such as potassium carbonate, sodium carbonate, potassium hydrogen
carbonate, sodium hydrogen carbonate, and sodium hydride. These bases may be used
in a range of 0.1 equivalents to 50 equivalents relative to 1 equivalent of the compound of
Formula (2). These bases may be used singly or in combination of two or more of them.
47
[0172] As the reaction temperature, any temperature from -78°C to the reflux
temperature of the reaction mixture can be set. Although the reaction time varies
depending on the concentration of the reaction substrate and the reaction temperature,
usually any time may be set in a range of 5 minutes to 100 hours.
5 [0173] Production method C
The compound of Formula (1-2): [where W, Q and R3 mean the same as defined
above] of the present invention can be produced, for example, by reacting the compound
of Formula (1-1): [where W, Q and R3 mean the same as defined above] of the present
invention with sulfidizing agents such as phosphorus pentasulfide, phosphorus
10 ; pentasulfide-HMDO (hexamethyldisiloxane), and Lawesson's reagent
(2,4-bis(4-methoxyphenyl)-l,3,2,4-dithiadiphosphetane-2,4-disulfide).
3
)
[0174] The sulfidizing agent used in this reaction can be used in a range of 0.5
15 equivalents to 50 equivalents relative to 1 equivalent of the compound of Formula (1-1).
Bases such as potassium carbonate, triethylamine, pyridine, and
4-(dimethylamino)pyridine can be used if necessary.
[0175] This reaction can be carried out without using a solvent. However, a
solvent may be used. Examples of the solvent may include polar solvents such as
20 N,N-dirnethylformamide, 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
48
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 -60°C to the reflux temperature
5 of the reaction mixture can be set. Although the reaction time varies depending on the
concentration of the reaction substrate and the reaction temperature, usually any time
may be set in a range of 5 minutes to 100 hours.
[0176] In the production method A to the production method C, usual post
treatment of the reaction mixture after completion of the reaction such as direct
10 concentration, concentration after dissolving in an organic solvent and washing with
water, or concentration after pouring into 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, column chromatography, thin layer chromatography, and liquid
15 chromatography.
Some of the compound of Formula (3b) can be synthesized in accordance with the
reaction formula 1 described below.
[0177] Production method D
The heterocyclic amide compound of Formula (1-1) can be produced by, for
20 example, reacting the compound of Formula (1-3): [where W and Q mean the same as
defined above] with the compound of Formula (4): [where R3 has the same as defined
above and J is a leaving group such as a halogen atom, -OH, -OSC^Me, and -OSO2CF3].
49
[0178] In this reaction, the compound of Formula (4) can be used in a range of
' 0.5 equivalents to 50 equivalents relative to 1 equivalent of the compound of Formula
(1-3). Acids such as hydrochloric acid, sulfuric acid, and p-toluenesulfonic acid or
5 bases such as potassium carbonate, triethylamine, pyridine, and
4-(dirnethylamino)pyridine, sodium hydride, sodium hydroxide, and potassium hydroxide
can be used if necessary. Alternatively, Mitsunobu reaction using diethyl
i azodicarboxylate, triphenylphosphine, and the like can be used.
i
[0179] This reaction can be carried out without using a solvent. However, a
10 solvent may be used. Example of the solvent 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
15 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.
[0180] As the reaction temperature, any temperature from -60°C to the reflux
temperature of the reaction mixture can be set. Although the reaction time varies
20 depending on the concentration of the reaction substrate and the reaction temperature,
usually any time may be set in a range of 5 minutes to 100 hours.
Some of the compounds of Formula (4) are known compounds and some of the
50
compounds are commercially available. Compounds other than the compounds
described above can be synthesized in accordance with methods described in reference
documents.
[0181] Reaction Formula 1
The compound of Formula (3b) can be produced by, for example, reacting the
compound of Formula (3a) with a halogenating agent.
a
[0182] The compound of Formula (3b): [where W, X and Xa mean the same as
10 defined above] can be produced by reacting the compound of Formula (3a) [where W and
X mean the same as defined above] or the salt thereof with the halogenating agent in a
solvent or without using a solvent by using a base if necessary.
Examples of the halogenating agent may include thionyl chloride, oxalyl chloride,
and phosphoryl chloride. The halogenating agent can be used in a range of 0.1
15 equivalents to 100 equivalents relative to 1 equivalent of the compound of Formula (3a).
[0183] When the solvent is used, the solvent to be used may be a solvent that is
inactive to the reaction. Example of the solvent may include polar solvents such as
N,N-dimethylformamide, N,N-dimethylacetamide, acetonitrile, dimethylsulfoxide, and
l,3-dimethyl-2-imidazolmone; ethers such as diethyl ether, tetrahydrofuran, 1,4-dioxane,
20 1,2-dimethoxyethane, and diphenyl ether; aromatic hydrocarbons such as benzene,
toluene, and xylene; halogenated hydrocarbons such as methylene chloride, chloroform,
carbon tetrachloride, and 1,2-dichloroethane; and aliphatic hydrocarbons such as
n-pentane and n-hexane. These solvents may be used singly or in combination of two or
more of them.
25 [0184] When the base is used, examples of the base to be used may include
51
organic bases such as triethylamine, pyridine, and 4-(dimethylamino)pyridine and
inorganic bases such as potassium carbonate, sodium carbonate, potassium hydrogen
carbonate, sodium hydrogen carbonate, and sodium hydride. These bases may be used
in a range of 0.1 equivalents to 50 equivalents relative to 1 equivalent of the compound of
5 Formula (3a). These bases may be used singly or in combination of two or more of
them.
[0185] As the reaction temperature, any temperature from -78°C to the reflux
temperature of the reaction mixture can be set. Although the reaction time varies
depending on the concentration of the reaction substrate and the reaction temperature,
10 k usually any time may be set in a range of 5 minutes to 100 hours.
The usual post treatment for the reaction mixture after completion of the reaction
can give a production intermediate serving as a starting material compound for the
production method B.
The production intermediate produced by this method can be used in the following
15 step without isolation and purification.
[0186] Specific examples of the active compound included in the present
invention may include the compounds listed in First Table to Third Table. The
compounds listed in First Table to Third Table, however, are compounds for
exemplification, and thus thp present invention is not limited to these compounds. In
20 Tables, the substituent described as Me is methyl group. Similarly in Tables, Et is ethyl
group, n-Pr and Pr-n are each normal-propyl group, i-Pr and Pr-i are each iso-propyl
group, c-Pr and Pr-c are each cyclopropyl group, n-Bu and Bu-n are each normal-butyl
group, s-Bu and Bu-s are each secondary-butyl group, an i-Bu and Bu-i are each iso-butyl
group, t-Bu and Bu-t are each tertiary-butyl group, c-Bu and Bu-c are each cyclobutyl
25 group, n-Pen and Pen-n are each normal-pentyl group, i-Pen and Pen-i are each iso-pentyl
group, s-Pen and Pen-s are each secondary-pentyl group, t-Pen and Pen-t are each
tertiary-pentyf group, c-Pen and Pen-c are each cyclopentyl group, 3-Pen is -CH(Et)2
group, n-Hex and Hex-n are each normal-hexyl group, c-Hex and Hex-c are each
cyclohexyl, and Ph is phenyl group.
52
[0187] In Tables, structures of D-3, D-3a, D-4, D-4a, D~4b, D-8, D-8a, D-8b,
D-8c, D-8d, D-8e, D-8fs D-8g, D-8h, D-9, D-9a, D-9b, D-9c, D-9d, D-9e, D-9f, D-9g,
D-9h, D-9i, D-9j, D- 9k, D-9m, D-lOa, D-ll, D-12, D-13a, D-14, D-15, D-16, D-16a,
D-16b, D-16c, D-16d, D-16e, D-16£ D-16g, D-16h, D-16i, D-16j, D-16k, D~16m, D-16n,
5 D-16p, D-17, D-17a, D-17b, D-18, D-19, D-21, D-24a, D-24b, D-24c, D-24d, D-24e and
D-24f are the following structures.
[0188]
108
canaliculatum, Sagittaria pygmaea, and Sagittaria trifolia; Gramineae weeds represented
by Leptochloa chinensis, Echinochloa crus-galli, Echinochloa oryzicola,
Homalocenchrus japonocus, and Paspalum distichum; Cyperaceae weeds represented by
Eleocharis kuroguwai, Scirpus juncoides, Scirpus nipponicus, Cyperus serotinus,
5 Cyperus difformis, and Cyperus hakonensis; Lemnaceae weeds represented by Spirodela
polyrhiza and Lemna paucicostata; Commelinaceae weeds represented by Murdannia
keisak; Pontederiaceae weeds represented by Monochoria korsakowii and Monochorea
vaginalis; Elatinaceae weeds represented by Elatine triandra; Lythraceae weeds
represented by Ammannia multiflora and Rotala indica; Oenotheraceae weeds
10 :. represented by Lidwigia epilobioides; Scrophulariaceae weeds represented by Dopatrium
junceum, Gratiolajaponica, Limnophila sessilifolia, Lindernia pyxidaria, and Lindernia
dubia; Leguminosae weeds such as Aeschynomene indica, and Compositae weeds
represented by, Bidens jrondosa and Bidens tripartita and the like.
[0193] The compound of the present invention can be used in any treatment
15 methods of soil treatment, soil incorporation treatment, and foliage treatment as a
herbicide for dry fields and orchards. Examples of the dry field weeds may include
broad-leaved weeds such as Solanaceae weeds represented by Solanum nigrum and
Datura stramonium; Geraniaceae weeds represented by Granium carolinianum;
Malvaceae weeds represented by Abutilon theophrasti and Sida spinosa; Convolvulaceae
20 weeds represented by Jpomoea spps. such as Ipomoea purpurea and Calystegia spps.;
Amaranthaceae weeds represented by Amaranthus lividus and Amaranthus retroflexus;
Compositae weeds represented by Xanthium pensylvanicum, Ambrosia artemisiaefolia,
Helianthus annuus, Galinsoga ciliata, Cirsium arvense, Senecio vulgaris, and Erigeron
annuus; Cruciferae weeds represented by Rorippa indica, Sinapis arvensis, and Capsella
25 Bursapastoris; Polygonaceae weeds represented by Polygonum Blumei and Polygonum
convolvulus; Portulacaceae weeds represented by Portulaca oleracea; Chenopodiaceae
weeds represented by Chenopodium album, Chenopodiumficifolium, and Kochia
scoparia; Caryophyllaceae weeds represented by Stellaria media; Scrophulariaceae
weeds represented by Veronica persica; Commelinaceae weeds represented by
109
Commelina communis; Labiatae weeds represented by Lamium amplexicaule and
Lamium purpureum; Euphorbiaceae weeds represented by Euphorbia supina and
Euphorbia maculate; Rubiaceae weeds represented by Galium spurium and Rubia akane;
Violaceae weeds represented by Viola mandshurica; Leguminosae weeds represented by
5 Sesbania exaltata and Cassia obtusifolia; and Oxsaldaseae represented by Oxsalis
courniculata; Graminaceous weeds represented by Sorgham bicolor, Panicum
dichotomiflorum, Sorghum halepense, Echinochloa crus-galli var. crus-galli,
Echinochloa crus-galli var. praticola, Echinochloa utilis, Digitaria ciliaris, Avenafatua,
Alopecurus myosuroides, Eleusine indica, Setaria viridis, Setariafaberi, and Alopecurus
10, aegualis; and Cyperaceous weeds represented by Cyperus rotundus and Cyperus
esculentus and the like.
[0194] The compound of the present invention can be used in any treatment
methods of soil treatment, soil incorporation treatment, and foliage treatment in
non-agricultural lands such as turfs, play grounds, open grounds, road verges, and railway
15 verges other than the agricultural and horticultural fields such as paddy fields, dry fields,
and orchards. As weeds in these non-agricultural lands, the following examples of the
weeds are exemplified in addition to those described as weeds in dry fields and orchards.
Examples of the weed may include Poa annua, Taraxacum officinale, Conyza
sumatrensis, Cardamine jlexuosa, Trifolium repens, Hydrocotyle sibthorpioides, Plantago
20 asiatica, Cyperus brevifolius, Kyllinga brevifolia, and Equisetum arvense and the like.
[0195] When the compound of the present invention is applied as the herbicide,
the compound is usually mixed with an appropriate solid carrier or liquid carrier, and
surfactants, penetrating agents, spreading agents, thickeners, antifreeze agents, binders,
anti-caking agents, disintegrating agents stabilizing agents and the like are added, if
25 desired. The herbicide can be applied to practical uses by any herbicide formulation of
the herbicide form such as water-dispersible agents, emulsion agents, flowable agents,
dry-flowable agents, liquid agents, powder agents, granule agents, or gel agents. From
the viewpoint of labor saving and improvement in safety, any of the herbicide
formulation of the herbicide form can be applied in an encapsulated state in a
no
water-soluble package.
[0196] Examples of the solid carriers may include natural minerals such as
quartz, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, and
diatomaceous earth; inorganic salts such as calcium carbonate, ammonium sulfate,
5 sodium sulfate and potassium chloride; and synthetic silicic acid and synthetic silicates.
[0197] Examples of the liquid carriers may include alcohols such as ethylene
glycol, propylene glycol, and isopropanol; aromatic hydrocarbons such as xylene,
alkylbenzene, and alkylnaphthalene; ethers such as butylcellosolve; ketones such as
cyclohexanone; esters such as y-butyrolactone; acid amides such as N-methylpyrrolidone
10 :. and N-octylpyrrolidone; vegetable oils such as soybean oil, rapeseed oil, cotton seed oil,
and castor oil; and water.
These solid carriers and liquid carriers may be used singly or in combination of two
or more of them.
[0198] Examples of the surfactant may include nonionic surfactants such as
15 polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene
styrylphenyl ethers, polyoxyethylene-polyoxypropylene block copolymers,
polyoxyethylene fatty acid esters, sorbitan fatty acid esters, and polyoxyethylene sorbitan
fatty acid esters; anionic surfactants such as alkyl sulfates, alkylbenzene sulfonates, lignin
sulfonates, alkyl sulfosuccinates, naphthalene sulfonate, alkylnaphthalene sulfonates,
20 salts of formalin condensate of naphthalene sulfonic acid, salts of formalin condensate of
alkylnaphthalene sulfonic acid, polyoxyethylene alkylaryl ether sulfates and phosphates,
polyoxyethylene styrylphenyl ether sulfates and phosphates, polycarboxylates, and
polystyrene sulfonates; cationic surfactants such as alkylamine salts and alkyl quaternary
ammonium salts; and amphoteric surfactants such as amino acid-type surfactants and
25 betaine-type surfactants.
[0199] The content of the surfactants is not particularly limited. Usually, the
content is preferably in a range of 0.05 parts by weight to 20 parts by weight relative to
100 parts by weight of the herbicide formulation of the present invention. These
surfactants may be used singly or in combination of two or more of them.
I ll
The compound of the present mvention may be applied in a mixed state with
another herbicide, various insecticides, a bactericide, a plant growth regulator, a synergist,
or the like at the time of herbicide formulation or application.
In particular, by applying the herbicide in a mixed state with another herbicide,
5 reduction in cost by reduction in an application amount, expansion in herbicidal spectrum
by synergistic action of mixed herbicides, and a higher herbicidal effect can be expected.
At this time, a combination of a plurality of known herbicides at the same time is also
possible.
[0200] Examples of the preferable herbicide used in a mixture with the
10 \ compound of the present invention may include acetochlor / general name, acifluorfen /
general name, aclonifen / general name, alachlor / general name, alloxydim / general
name, alloxydim- sodium / general name, ametryn / general name, amicarbazone /
general name, amidosulfuron / general name, aminocyclopirachlor / general name,
amino cyclopirachlor-salts and esters, aminopyralid / general name, aminopyralid-salts
15 and esters, amiprophos-methyl / general name, amitrol / general name, anilofos / general
name, asulam / general name, atrazine / general name, azafenidin / general name,
azimsulfiiron / general name, beflubutamid / general name, benazolin-ethyl / general
name, bencarbazone / general name, benfluralin (benefin) / general name, benfiiresate /
general name, bensulfuron-methyl / general name, bensulide / general name, bentazone /
20 general name, bentazone-sodium / general name, bentazone-salts, benthiocarb / general
name, benzfendizone / general name, benzobicyclon / general name, benzofenap / general
name, bialaphos / general name, bialaphos-sodium / general name, bicyclopyrone /
general name, bifenox / general name, bispyribac / general name, bispyribac-sodium /
general name, bromacil / general name, bromobutide / general name, bromofenoxim /
25 general name, bromoxynil / general name, bromoxynil-salts and esters, butachlor /
general name, butafenacil / general name, butamifos / general name, butenachlor /
general name, butralin / general name, butroxydim / general name, butylate / general
name, cafenstrole / general name, carbetamide / general name, carfentrazone-ethyl,
chlomethoxyfen / general name, chlomethoxynil / general name, chloramben / general
112
name, chloramben-salts and esters, chloransulam-methyl / general name,
chlorflurenol-methyl / general name, chloridazon / general name, chlorimuron-ethyl /
general name, chlorobromuron / general name, chlorotoluron / general name, chloroxuron
/ general name, chlorphtalim / general name, chlorpropham / general name, chlorpropham
5 / general name, chlorsulfuron / general name, chlorthal-dimethyl / general name,
chlorthiamid / general name, cinidon-ethyl / general name, cinmethylin / general name,
cinosulfuron / general name, clethodim / general name, clodinafop / general name,
clodinafop-propargyl / general name, clomazone / general name, clomeprop / general
name, clopyralid / general name, clopyralid-salts and esters, CNP / general name,
10 :. cumyluron / general name, cyanazin / general name, cycloate / general name,
cyclopyrimorate / general name (SW-065/ test name), cyclosulfamuron / general name,
cycloxydim / general name, cyhalofop-butyl / general name, DAH-500/ test name,
dalapon / general name, dazomet / general name, desmedipham / general name,
desmetryn / general name, dicamba / general name, dicamba-salts and esters, dichlobenil
15 / general name, diclofop / general name, diclo fop-methyl / general name, dichlorprop /
general name, dichlorprop-salts and esters, dichlorprop-P / general name,
dichlorprop-P-salts and esters, diclosulam / general name, difenzoquat / general name,
diflufenican / general name, diflufenzopyr / general name, diflufenzopyr-sodium / general
name, dimepiperate / general name, dimethametryn / general name, dimethachlor /
20 general name, dimethenamid / general name, dimethenamid-p / general name, dimethipin
/ general name, dinitramine / general name, dinoseb / general name, dinoterb / general
name, DNOC / general name, diphenamid / general name, diquqt / general name,
dithiopyl / general name, diuron / general name, DSMA / general name, dymron / general
name, endothal / general name, EPTC / general name, esprocarb / general name,
25 ethalfluralin / general name, ethametsulfuron-methyl / general name, ethofiimesate /
general name, etobenzanid / general name, ethoxysulfuron / general name, flazasuhuron /
general name, fenoxaprop / general name, fenoxaprop-ethyl / general name,
fenoxasulfone / general name, fenquionotrion / general name, fentrazamide / general
name, flamprop / general name, flazasulfuron / general name, florasulam / general name,
113
fluazifop / general name, fluazifop-butyl / general name, fluazolate / general name,
flucarbazone-sodium / general name, fluceto sulfur on / general name, flucloralin / general
name, flufenacet / general name, flufenpyl-ethyl / general name, flumetsulam / general
name, flumiclorac-pentyl / general name, flumioxazin / general name, fluometuron /
5 general name, fluoroglycofen-ethyl / general name, flupyrsulforon / general name,
flupoxam / general name, flurenol / general name, fluridone / general name,
flurochloridone / general name, fluroxypyr / general name, fluroxypyr-esters,
flurprimidol / general name, flurtamone / general name, fluthiacet-methyl / general name,
fomesafen / general name, foramsulfuron / general name, fosamine / general name,
10, glufosinate / general name, glufosinate-ammonium / general name, glyphosate / general
name, glyphosate-ammonium / general name, glyphosate-iso-propylammonium / general
name, glyphosate-potassium / general name, glyphosate-sodium / general name,
glyphosate-trimesium / general name, halauxifen / general name, halauxifen-salts and
esters, halosafen / general name, halosulfuron / general name, halo su Huron-methyl /
15 general name, haloxyfop / general name, haloxyfop-methyl / general name, hexazinone /
general name, imazamethabenz-methyl / general name, imazamox / general name,
imazapic / general name, imazapyr / general name, imazethapyr / general name,
imazaquin / general name, imazosulfuron / general name, indanofan / general name,
indaziflam / general name, iodosuliuron-methyl-sodium / general name, ioxynil octanoate
20 / general name, ioxynil-salts and esters, ipfencarbazone / general name, isoproturon /
general name, isouron / general name, isoxaben / general name, isoxaflutole / general
name, karbutilate / general name, lactofen / general name, lenacil / general name, linuron
/ general name, maleic hydrazide / general name, MCPA/ general name, MCPA-salts and
esters, MCPB / general name, MCPB-salts and esters, mecoprop (MCPP) / general name,
25 mecoprop-salts and esters, mecoprop-P (MCPP-P) / general name, mecoprop-P-salts and
esters, mefenacet / general name, mefluidide / general name, mesosulfuron-methyl /
general name, mesotrione / general name, metam / general name, metamifop / general
name, metamitron / general name, metazachlor / general name, methabenzthiazuron /
general name, metazosulfuron / general name, methiozolin / general name, methyl azide /
114
general name, methyl bromide / general name, methyl dymron / general name, methyl
iodide / general name, metobenzuron / general name, metolachlor / general name,
metolachlor-S / general name, metosulam / general name, metribuzin / general name,
metsulluron-methyl / general name, metoxuron / general name, molinate / general name,
5 monolinuron / general name, monosulfuron / general name, monosulfuron-methyl /
general name, MSMA / general name, naproamlide / general name, napropamide /
general name, naptalam / general name, naptalam- sodium / general name, neburon /
general name, nicosulfuron / general name, norflurazon / general name, OK-701/ test
name, oleic acid / general name, orbencarb / general name, orthosulfamuron / general
10 ...... name, oryzalin / general name, oxadiargyl / general name, oxadiazon / general name,
oxasulfuron / general name, oxaziclomefone / general name, oxyfluorfen / general name,
paraquat / general name, pelargonicacid / general name, pendimethalin / general name,
penoxsulam / general name, pentanochlor / general name, pentoxazone / general name,
pethoxamid / general name, phenmedipham-ethyl / general name, picloram / general
15 namep picloram-salts and esters, picolinafen / general name, pinoxaden / general name,
piperophos / general name, pretilachlor / general name, primisulfuron-methyl / general
name, prodiamine / general name, profluazol / general name, profoxydim / general name,
prometon / general name, prometryn / general name, propachlor / general name, propanil
/ general name, propaquizafop / general name, propazin / general name, propham /
20 general name, propisochlor / general name, propoxycarbazone-sodium / general name,
propyrisulfuron / general name, propyzamide / general name, prosulfocarb / general name,
prosulfuron / general name, pyraclonil / general name, pyraflufen-ethyl / general name,
pyrasulfotole / general name, pyrazolynate / general name, pyrazosulfuron / general name,
pyrazosulfuron-ethyl / general name, pyrazoxyfen / general name, pyribenzoxim / general
25 name, pyributicarb / general name, pyridafol / general name, pyridate / general name,
pyriftalid / general name, pyriminobac-methyl / general name, pyrimisulfan / general
name, pyrithiobac-sodium / general name, pyroxasulfone / general name, pyroxsulam /
general name, quinclorac / general name, quinmerac / general name, quinoclamine /
genen.l name, quizalofop / general name, quizalofop-ethyl / general name,
115
quizalofop-tefiiryl / general name, quizalofop-P / general name, quizalofop-P-ethyl /
general name, quizalofop-P-tefiiryl / general name, rimsulfuron / general name,
saflufenacil / general name, sethoxydim / general name, siduron / general name, simazine
/ general name, simetryn / general name, SL-261/ test name, sulcotrione / general name,
5 sulfentrazone / general name, sulfometuron-methyl / general name, sulfosulfuron /
general name, TCBA (2,3,6-TBA) / general name, 2,3,6-TBA-salts and esters, TCTP
(chlorthal-dimethyl, tetorachlorothiophene) / general name, tebutam /general name,
tebuthiuron / general name, tefuryltrione / general name, tembotrione / general name,
tepraloxydim / general name, terbacil / general name, terbumeton / general name,
10 .,., terbuthylazine / general name, terbutryn / general name, tetrapion (flupropanate) / general
name, thenylchlor / general name, thiazafluron / general name, thiazopyr / general name,
thidiazimin / general name, thidiazuron / general name, thiencarbazone-methyl / general
name, thifensulfuron-methyl / general name, tolpyralate / general name, topramezon /
general name, tralkoxydim / general name, triafamone / general name, triallate / general
15 name, triasulfiiron / genera^ name, triaziflam / general name, tribenuron-methyl / general
name, triclopyr / general name, triclopyr-salts and esters, tridiphane / general name,
trietazine / general name, trifludimoxadin / general name, trifloxysulfuron / general name,
trifluralin / general name, triflusulfuron-methyl / general name, tritosulfuron / general
name, 2,4-PA / general name, 2,4-PA-salts and esters, 2,4-DB / general name, and
20 2,4-DB-salts and esters. These components may be used singly or in combination of
two or more of them. When these components are mixed, the mixing ratio may be
freely selected.
[0201] Examples of safeners may include AD-67, benoxacor / general name,
cloquintocet-mexyl / general name, cyomerinil / general name, dichlormid / general name,
25 dicyclonone / general name, cyprosulfamide / general name, diethorate / general name,
DKA-24, dymron / general name, fenclorazole-ethyl / general name, fenclorim / general
name, HEXIM / general name, flurazole / general name, fluxofenim / general name,
furilazole / general name, isoxadifen / general name, isoxadifen-ethyl / general name,
MCPA, mecoprop / general name, mefenpyr / general name, mefenpyr-ethyl / general
116
name, mefenpyr-diethyl / general name, mephenate / general name, MG-191, NA
(Naphthalic anhydride), OM (Octamethylene-diamine), oxabetrinil / general name,
PPG-1292, and R-29148. These agricultural chemical active components may be used
singly or in combination of two or more of them. When these components are mixed,
5 the mixing ratio may be freely selected.
[0202] Although the application amount of the compound of the present
invention varies depending on the application situation, the application time, the
application method, the cultivated crop and the like, the appropriate application amount is
generally 0.005 kg/ha to 50 kg/ha as the amount of the active component.
10 ,, [0203] Next, the formulation examples of the herbicide formulations when the
compound of the present invention is used will be described. However, the formulation
examples of the present invention are not limited to these examples. Hereinafter, the
term "part" in the formulation examples means part by weight.
Water-dispersible agent
15 Compound of the present invention 0.1 parts to 80 parts
Solid carrier 5 parts to 98.9 parts
Surfactant 1 part to 10 parts
Others 0 parts to 5 parts
Examples of Others may include anti-caking agents, stabilizing agents and the like.
20 [0204] Emulsion agent
Compound of the present invention 0.1 parts to 30 parts
Liquid carrier 45 parts to 95 parts
Surfactant 4.9 parts to 15 parts
Others 0 parts to 10 parts
25 Examples of Others may include spreading agents, stabilizing agents and the like.
[0205] Flowabie agent
Compound of the present invention 0.1 parts to 70 parts
Liquid carrier 15 parts to 98.89 parts
Surfactant 1 part to 12 parts

Claim
.5a • 5b Ria and KM are each independently a hydrogen atom, Ci_6 alkyl, (Ci^) alkyl
127 optionally substituted with R , C3-6 cycloalkyl, C3-6 halocycloalkyl, C2-6 alkenyl, C2-6
205
haloalkenyl, C2-6 aikynyl, C2-6 haloalkynyl, C3_6 cycloalkenyl, phenyl, or phenyl
substituted with (R28)r;
R5c is a hydrogen atom, Ci-e alkyl, or (Ci^) alkyl optionally substituted with R36, or
R5c optionally forms a 6-membered ring together with a nitrogen atom to which R5c is
5 bonded and a carbon atom to which R4d is bonded by forming -(CHbV or
-CH=CH-CH=CH- withR4d;
R6 is a halogen atom, cyano, C3-6 cycloalkyl, -C(0)R8, -C(0)OR16, -OR13,
-S(0)m2R14, phenyl, or phenyl substituted with (R7)p;
R7 is a halogen atom, cyano, nitro, Ci-e alkyl, (Ci^) alkyl optionally substituted with
10 -: R27, C3.6 cycloalkyl, C3.6 halocycloalkyl, C2-6 aikenyl, C2-6 haloalkenyl, C2-6 aikynyl, C2-6
haloalkynyl, C3.6 cycloalkenyl, Ci^ alkylcarbonyl, C3_6 cycloalkylcarbonyl, Ci_6
haloalkylcarbonyl, C3.6 halo cycloalkylcarbonyl, Ci_6 alkoxycarbonyl, Cs_6
haloalkoxycarbonyl, C1-6 alkylaminocarbonyl, Ci_6 haloalkylaminocarbonyl, di(Ci_6
alkylamino)carbonyl, -OR15, -SCO^R20, Ci* alkylaminosulfonyl, di(C]_6
15 alkyl)aminosulfonyl, -NH2, Ci-e alkylamino, di(Cj.^ alkyl)amino, 5-6-membered
heteroaryl, 5-6-membered heteroaryl (optionally substituted with R28 and R28a),
3-7-membered heterocyclyl, or 3-7-membered heterocyclyl (optionally substituted with
R28andR28a);
R8 is a hydrogen atom, Ci-e alkyl, or -N(Rlla)R12a;
20 R8b is a hydrogen atom or Ci_6 alkyl;
R9 is a hydrogen atom, C1-6 alkyl, or phenyl;
R10 is a hydrogen atom, C1.6 alkyl, (Ci^) alkyl optionally substituted with R , C3.6
cycloalkyl, C3-6 halocycloalkyl, C2-6 aikenyl, C2-6 haloalkenyl, C2-6 aikynyl, or C2-6
haloalkynyl;
25 RnandR12 are each independently a hydrogen atom, Ci-e alkyl, (C^) alkyl
optionally substituted with R34, C3-6 cycloalkyl, C2-6 aikenyl, C2-6 haloalkenyl, C2-6
aikynyl, C2-6 haloalkynyl, phenylsulfonyl, phenyl, phenyl substituted with (R7)P, U-7, U-8,
U-9, or U-14 to U-19, or R11 optionally forms a 3-7-membered ring together with a
nitrogen atom to which R11 and R12 are bonded by forming a C2-6 alkylene chain together
206
with R12, and in this case, the alkylene chain optionally contains one O, S, S(O), S(0)2, or
N(R33) and is optionally substituted with an oxo group or a thioxo group;
RtIaandRi2a are each independently a hydrogen atom, Ci-6 alkyl, or phenyl, or Rlia
optionally forms a 3-7-membered ring together with a nitrogen atom to which Rlla and
5 R12a are bonded by forming a C2-6 alkylene chain together with R12a, and in this case, the
alkylene chain optionally contains one O, S, S(O), S(0)2, or N(R33) and is optionally
substituted with an oxo group or a thioxo group;
R12bis-OR19b;
R13 is a hydrogen atom, Ci_6 alkyl, (Ci^) alkyl optionally substituted with R34, C2-6
10 -, alkenyl, C2^ haloalkenyl, C2-6 alkynyl, C2_6 haloalkynyl, -C(0)R8, or phenyl;
R14 is a hydrogen atom, Ci^ alkyl, (Ci-s) alkyl optionally substituted with R34, C2-6
alkenyl, C2-6 haloalkenyl, C2-6 alkynyl, C2_6 haloalkynyl, or phenyl;
R35 is a hydrogen atom, Ci_6 alkyl, (Ci^) alkyl optionally substituted with R27, C3-6
cycloalkyl, C3_6 halocycloalkyl, C2-6 alkenyl, C2-6 haloalkenyl, C2-6 alkynyl, C2.6
15 haloalkynyl, or C3.6 cycloalkenyl; t
R is a hydrogen atom, C1-6 alkyl, or (C1-6) alkyl optionally substituted with R ;
R18 is a hydrogen atom or C1-6 alkyl;
R19 is a hydrogen atom, C1-6 alkyl, or phenyl;
R19b is a hydrogen atom or Ci_6 alkyl;
20 R20 is C1-6 alkyl, Cj_6 haloalkyl, C3-6 cycloalkyl, C2-6 alkenyl, C2-6 haloalkenyl, C2~6
alkynyl, C2-6 haloalkynyl, or C3-6 cycloalkenyl;
R21 and R22 are each independently a hydrogen atom, Ci_6 alkyl, or phenyl, or R21
optionally forms a 3-7-membered ring together with a nitrogen atom to which R and R
are bonded by forming a C2-6 alkylene chain together with R22, and in this case, the
25 alkylene chain optionally contains one O, S, S(O), S(0)2, or N(R39) and is optionally
substituted with an oxo group or a thioxo group;
R24 is a hydrogen atom or Ci-6 alkyl;
R25 and R26 are each independently a hydrogen atom, Ci_6 alkyl, C1.6 haloalkyl, C3-6
cycloalkyl, C3-6 halocycloalkyl, C2-6 alkenyl, C2-6 haloalkenyl, C2-6 alkynyl, C2-6
207
haloalkynyl, C3-6 cycloalkenyl, or phenyl;
R27 is a halogen atom, cyano, nitro, phenyl, phenyl substituted with (R28)r,
-C(0)OR16, -OR29, -S(0)m4R30, 5-6-membered heteroaryl, 5-6-membered heteroaryl
(optionally substituted with R28 and R28a), 3-7-membered heterocyclyl, or 3-7-membered
5 heterocyclyl (optionally substituted with R28 and R28a);
R28 is a halogen atom, cyano, nitro, Ci_6 alkyl, Q-6 haloalkyl, C3-6 cycloalkyl, C3-6
halocycloalkyl, C2-6 alkenyl, C2-6 haloalkenyl, C2-6 alkynyl, C2-6 haloalkynyl, (d-e
alkoxy) d* alkyl, -OR31, or -S(0)m4R3°; when t2, t3, t4, t5, t7, t8, or t9 is an integer of 2
or more, R28 are optionally the same as or different from each other; further when two R
10..;. are adjacent, the two adjacent R28 optionally form a 6-membered ring together with
carbon atoms to which each R is bonded by forming -CH=CH-CH=CH-;
R28a is C1-6 alkyl, d~6 haloalkyl, (d-6 alkoxy) d-6 alkyl, or (d-6 alkylthio) d-6
alkyl;
R29, R30, and R31 are each independently a hydrogen atom, C1-6 alkyl, d-6 haloalkyl,
15 C3-6 cycloalkyl, d-6 halocycloalkyl, d-6 alkenyl, d-6 haloalkenyl, C2-6 alkynyl, C2-6
haloalkynyl, C3-6 cycloalkenyl, or phenyl;
R33 is a hydrogen atom or d-6 alkyl;
R34 is a halogen atom, cyano, C3-6 cycloalkyl, -C(0)R8, ~C(0)OR16, -OR33,
-S(0)m6R33, phenyl, phenyl substituted with (R7)P, U-1, U-3, U-7, U-8, U-9, or U-14 to
20 U-25;
R35 is a halogen atom or Ci_6 alkoxy;
R36 is a halogen atom or Ci_6 alkoxy;
R37 is C1-6 alkoxy,
R38 is C1.6 alkyl, (Ci-e) alkyl optionally substituted with R34, C3-6 cycloalkyl, C3-6
25 halocycloalkyl, C2-6 alkenyl, C2-6 haloalkenyl, C2-6 alkynyl, C2-6 haloalkynyl, C3-6
cycloalkenyl, or phenyl;
R39 is a hydrogen atom or C1-6 alkyl;
tl is an integer of 0 or 1;
ml, m2, m3, m4, m6, and t2 are each independently an integer of 0, 1, or 2;
208
n and t3 are each independently an integer of 0,1,2, or 3;
p and r are each independently an integer of 1, 2, 3, 4, or 5;
t4 is an integer of 0, 1, 2, 3, or 4;
t5 is an integer of 0, 1, 2, 3, 4, or 5;
5 t7 is an integer of 0, 1,2, 3,4, 5, 6, or 7;
t8 is an integer of 0, 1, 2, 3,4, 5, 6, 7, or 8; and
t9 is an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9] or a salt thereof.
2. The heterocyclic amide compound or the salt thereof according to claim 1,
10 . wherein W is an aromatic heterocycle of W-l or W-2; and
R2a is a halogen atom, Cs.6 alkyl, C3-6 haloalkyl, -C(0)Ri8, -C(0)OR24, cyano, nitro,
-OR19, or -S(0)m3R20, and when n is an integer of 2 or more, R2a are optionally the same
as or different from each other.
15 3. The heterocyclic amide compound or the salt thereof according to claim 2,
wherein Rlb is a hydrogen atom, Ci-e alkyl, (Ci-e) alkyl optionally substituted with R6,
C3-6 cycloalkyl, (C34) cycloalkyl optionally substituted with R6, C2-6 alkenyl, C2-6 alkynyl,
phenyl, phenyl substituted with (R7)P, naphthyl, or any one group of U-l to U-25;
R4a is a hydrogen atom, a halogen atom, Ci-e alkyl, (Ci^) alkyl optionally
20 substituted with R27, C3-6 cycloalkyl, (C3-6) cycloalkyl optionally substituted with R27,
C2~6 alkenyl, C2-6 haloalkenyl, C2-6 alkynyl, C2-6 haloalkynyl, C3-6 cycloalkenyl, -NH2,
Ci„6 alkylamino, di(Ci_6 alkyl)amino, -NHC(0)R , phenyl, phenyl substituted with (R )r,
or any one group of U-l to U-26;
R7 is a halogen atom, cyano, nitro, Ci_6 alkyl, (Ci-e) alkyl optionally substituted with
25 R27, C3-6 cycloalkyl, C3-6 halocycloalkyl, C2-6 alkenyl, C2-6 haloalkenyl, C2-6 alkynyl, C2-6
haloalkynyl, C3-6 cycloalkenyl, C1-6 alkylcarbonyl, C3-6 cycloalkylcarbonyl, Ci_6
haloalkylcarbonyl, C3-6 halocycloalkylcarbonyl, C1-6 alkoxycarbonyl, Ci^
haloalkoxycarbonyl, Ci_6 alkylaminocarbonyl, C3_6 haloalkylaminocarbonyl, di(Ci_6 alkyl
amino)carbonyl, -OR15, -S(0)m3R20, Ci_e alkylaminosulfonyl, di(Ci_6 aikyl)aminosulfonyl,
209
-NH2, Cj.6 alkylamino, di(Ci-6 alkyl)amino, or any one group of U-l to U-26; and
R 27
is a halogen atom, cyano, nitro, phenyl, phenyl substituted with (R28)r,
-C(0)OR16, -OR29, -S(0)m4R3°, or any one group of U-l to U-26.
5 4. The heterocyclic amide compound or the salt thereof according to claim 3,
wherein R1a is a hydrogen atom, a halogen atom, Ci_6 alkyl, (Ci-e) alkyl optionally
substituted with R6, C3-6 cycloalkyl, (C3-6) cycloalkyl optionally substituted with R6, C2-6
alkenyl, C2-6 alkynyl, C3-6 cycloalkenyl, -C(0)R8, -OR9, -S(0)m!R10, -N(Rn)R12,
~C(=NR12b)R8b, phenyl, phenyl substituted with (R7)p, U-3, U-5a, U-6a, U-7, U-8, U-lOa,
10-;. U-lla,U-12a,orU-13a;
Rlb is Ci_6 alkyl or (Ci^) alkyl optionally substituted with R6;
R2a is a halogen atom, C1-6 alkyl, Ci_6 haloalkyl, or -S(0)m3R20, and when n is an
integer of 2 or more, R2a are optionally the same as or different from each other;
R3 is a hydrogen atom or C1-6 alkyl;
15 R4a is a hydrogen atom, C1-6 alkyl, (Ci-e) alkyl optionally substituted with R27, C3-6
cycloalkyl, phenyl, phenyl substituted with (R )r, or a heterocycle of U-l, U-2, U-7,
U-10a,orU-26;
R4b is C^ alkyl;
R4c is a hydrogen atom;
20 R4d is C1.6 alkyl;
R5a is a hydrogen atom, C^ alkyl, (Ci^) alkyl optionally substituted with R27, C2^
alkenyl, or phenyl;
R5b is a hydrogen atom or Ci_6 alkyl;
R5c is Cj_6 alkyl, or R5c optionally forms a 6-membered ring together with a nitrogen
25 atom to which R5c is bonded and a carbon atom to which R4d is bonded by forming
-(CH2)4- or -CH-CH-CH-CH- with R4d;
R' is a halogen atom, C1-6 alkyl, (Ci-e) alkyl optionally substituted with R , or
-OR15;
R8b is a hydrogen atom;
210
R9 is Ci.6 alkyl;
R10 is Ci^ alkyl, (Ci^) alkyl optionally substituted with R34, C3_6 cycloalkyl, C2-6
alkenyl, or C2-6 alkynyl;
R11 is C1-6 alkyl, (Ci-e) alkyl optionally substituted with R34, C3-6 cycloalkyl, C2^
5 alkenyl, C2-6 alkynyl, phenylsulfonyl, phenyl, phenyl substituted with (R7)p, or U-7;
R12 is a hydrogen atom or Ci-6 alkyl;
R11 optionally forms a 5-6-membered ring together with a nitrogen atom to which
R11 and R12 are bonded by forming a C4-5 alkylene chain together with R12, and in this
case, the alkylene chain optionally contains one O, S, S(O), or S(0)2;
10,. Rl l a is C1.6 alkyl;
R12a is a hydrogen atom;
R13 is a hydrogen atom, C1-6 alkyl, (Ci^) alkyl optionally substituted with R34,
-C(0)R8, or phenyl;
R14 is Ci_6 alkyl or (Ci-e) alkyl optionally substituted with R34;
15 R15 is C1-6 alkyl;
R19b is C1-6 alkyl;
R20 is C1.6 alkyl;
R27 is a halogen atom, phenyl, phenyl substituted with (R28)r, -OR29, -C(0)OR16, or
-S(0)m4R3°;
20 R28 is a halogen atom, Ci_6 alkyl, or -OR31; when t2, t3, t4, t5, or t7 is an integer of 2
or more, R28 are optionally the same as or different from each other; and fiirther when
two R28 are adjacent, the two adjacent R28 optionally form a 6-membered ring together
with carbon atoms to which each R28 is bonded by forming -CH=CH-CH=CH-;
R29isCi_6alkyl;
25 R30 is C1-6 alkyl;
R3i is C1-6 alkyl;
R33 is Ci-e alkyl; and
R34 is a halogen atom, cyano, C3-6 cycloalkyl, -C(0)R8, -C(0)OR16, -OR33,
-S(0)ra6R33, phenyl, phenyl substituted with (R7)p, U-l, U-8, or U-22a.
211
5. The heterocyclic amide compound or the salt thereof according to claim 4,
wherein Q is an aromatic heterocycle of Q-l; and
W is an aromatic heterocycle of W-1.
5
6. The heterocyclic amide compound or the salt thereof according to claim 5,
wherein X is an oxygen atom;
Rla a hydrogen atom, a halogen atom, Ci-6 alkyl, (Ci_6) alkyl optionally substituted
with R6, C3_6 cycloalkyl, (C3-6) cycloalkyl optionally substituted with R6, C2-e alkenyl,
10, C2-6 alkynyl, C3-6 cycloalkenyl, -C(0)R8, -OR9, -S(O)mlRj0, -N(Rn)R12, -C(=NR12b)R8b,
phenyl, phenyl substituted with (R7)p, U-5a, U-6a, U-7, U-8, U-lOa, U-lla, U-12a, or
U-13a;
R2a is a Ci^ alkyl, Ci-6 haloalkyl, or -S(0)m3R20, and when n is an integer of 2 or
more, R2a are optionally the same as or different from each other;
15 R6 is a halogen atom, cyano, C3_6 cycloalkyl, -C(0)R8, -C(0)OR16, -OR13,
-Stp^R14, or phenyl substituted with (R7)p; and
R is a halogen atom, phenyl, -OR , or -S(0)m4R •
7. The heterocyclic amide compound or the salt thereof according to claim 6,
20 wherein R4a is a hydrogen atom, Ci_6 alkyl, (C\^) alkyl optionally substituted with R27, or
C3_6 cycloalkyl; and
R is a halogen atom or -OR .
8. The heterocyclic amide compound or the salt thereof according to claim 4,
25 wherein Q is an aromatic heterocycle of Q-3; and
W is an aromatic heterocycle of W-l.
9. The heterocyclic amide compound or the salt thereof according to claim 8,
wherein Rla is a hydrogen atom, a halogen atom, Ci^ alkyl, (C^) alkyl optionally
212
substituted with R6, Cs^ cycloalkyl, (C3.6) cycloalkyl optionally substituted with R6, C2-6
alkenyl, Clr6 alkynyl, -C(0)R8, -S(0)m3R10, -N(Rn)R12, phenyl, phenyl substituted with
(R7)P, U-3, U~5a, U-6a, U-8, U-lOa, or U-13a;
R2a is a halogen atom, Ci-6 alkyl, or Ci_6 haloalkyl, and when n is an integer of 2 or
5 more, R2a are optionally the same as or different from each other;
R6 is a halogen atom, -C(0)OR16, -OR13, -S(0)m2RM, or phenyl substituted with
(R7)P;
R7 is a halogen atom, C\* alkyl, or -OR15;
R8 is a hydrogen atom or C1-6 alkyl;
10 - R11 is C1-6 alkyl, (Ci^) alkyl optionally substituted with R34, C3-6 cycloalkyl, C2-6
alkenyl, C2-6 alkynyl, phenyl, or phenyl substituted with (R7)p;
R!! optionally forms a 6-membered ring together with a nitrogen atom to which R11
and R12 are bonded by fonning a C5 alkylene chain together with R12, and in this case, the
alkylene chain optionally contains one O, S, S(O), or S(0)2;
15 ^R16 is a hydrogen atom or Ci_6 alkyl;
R27 is phenyl substituted with (R28)r, -OR29, -C(0)OR16, or -S(0)m4R3°;
R28 is a halogen atom or C\* alkyl; and
R34 is a halogen atom, cyano, C3-6 cycloalkyl, -OR , -S(0)m6R33, phenyl, phenyl
substituted with (R7)p, U-l, or U-8.
20
10. The heterocyclic amide compound or the salt thereof according to claim 9,
wherein R5a is Ci_6 alkyl, (Ci^) alkyl optionally substituted with R27, or C2-6 alkenyl; and
R27is-OR29or-S(0)m4R3°.
25 11. An agricultural chemical comprising one or two or more of compounds selected
from the heterocyclic amide compound and the salt thereof as claimed in claim 1 or 2 as
an active component.
12. A herbicide comprising one or two or more of compounds selected from the
213
heterocyclic amide compound and the salt thereof as claimed in claim 1 or 2 as an active
component.