WO2008044713A1 - Substituted pyridinecarboxanilide derivative or salt thereof, and agricultural or horticultural agent, and use thereof - Google Patents

Abstract

Disclosed are: a substituted pyridinecarboxanilide derivative represented by the general formula (I) or a salt thereof; an agricultural or horticultural agent comprising the compound as an active ingredient; and use of the agent. It becomes possible to provide a novel agricultural or horticultural agent, particularly a pesticidal agent or a miticidal agent. (I) wherein R1 represents H, an alkyl, an alkylcarbonyl, a cycloalkyl, a phenylalkyl, a phenylcarbonyl, a cyanoalkyl, or the like; R2 represents H, a halogen, an alkyl, CN, OH, an alkoxy, a phenoxy, a phenylthio, a phenylsulfonyl, or the like; G represents an alkyl, an alkenyl, an alkynyl, a cycloalkyl, a cycloalkenyl, or the like; Z represents O or S; X represents a halogen, CN, NO2, an alkyl, or the like; Y represents a halogen, CN, NO2, OH, a mercapto, an amino, a carboxyl, an alkyl, a phenyl, a phenoxy, a heterocyclic group, or the like; m represents a number of 0 to 4; and n represents a number of 0 to 3.

Description

 Specification

 Substituted pyridinecarboxylic acid anilide derivatives or salts thereof, agricultural and horticultural agents and methods of use

 Technical field

 [0001] The present invention relates to a substituted pyridinecarboxylic acid anilide derivative and a salt thereof, an agricultural and horticultural drug containing the compound as an active ingredient, particularly an insecticide or acaricide, and a method of using the same.

 Background art

 Conventionally, it is known that substituted pyridinecarboxylic acid amide derivatives similar to the present invention are useful as agricultural and horticultural insecticides, fungicides or acaricides (see, for example, Patent Documents 1 and 2). In the substituted pyridinecarboxylic acid anilide derivative disclosed in Patent Document 1, the substituent of the aniline moiety is limited to the 2-position substitution product, and the compound in which an alkyl group is introduced at the 3-position described in the present invention is disclosed. Absent. Furthermore, the substituted pyridine strength rubonic acid anilide derivatives specifically disclosed therein show acaricidal activity! /, Na! / ,. Further, in the substituted pyridinecarboxylic acid anilide derivative disclosed in Patent Document 2, the substituent of the aniline moiety is limited to an alkoxy group, and a compound in which an alkyl group is directly introduced at the 3-position described in the present invention is not disclosed. .

 Patent Document 1: Japanese Patent Laid-Open No. 2003-48878

 Patent Document 2: JP 2004-189738 A

 Disclosure of the invention

 Problems to be solved by the invention

[0003] In crop production such as agriculture and horticulture, the development of new agricultural and horticultural agents, in particular insecticides or acaricides, due to factors such as the occurrence of pests that are resistant to existing drugs is still significant. It is desired. Moreover, various labor-saving application methods are required due to the aging of farmers, and the creation of agricultural and horticultural agents, particularly insecticides or acaricides, having characteristics suitable for these application methods.

Means for solving the problem [0004] As a result of intensive research aimed at developing novel agricultural and horticultural agents, in particular insecticides or acaricides, the present inventors have found that, among the wide range of compounds described in the above-mentioned conventional literature, heterocyclic strength rubon. A pyridine ring is selected as the acid moiety, and a specific substituent is introduced at the 3-position of the aniline moiety. The substituted pyridinecarboxylic acid anilide derivative represented by the general formula (I) of the present invention is described in the above-mentioned conventional literature as an acaricide. The present invention has been found out to show an excellent control effect that could not be predicted from the content, and the present invention has been completed.

 That is, the present invention relates to the general formula (I)

 [0006] [Chemical 1]

[0007] {where R ¹ is

 (la) a hydrogen atom,

 (2a) a C 1 -C alkyl group,

 1 6

 (3a) a halo C 1 -C alkyl group,

 1 6

 (4a) C 1 -C alkylcarbonyl C 1 -C alkyl group,

 1 6 1 6

 (5a) C 1 -C cycloalkyl group,

 3 6

 (6a) a halo C -C cycloalkyl group,

 3 6

 (7a) C-C cycloalkyl C-C alkyl group,

 3 6 1 6

 (8a) a halo C-C cycloalkyl C-C alkyl group,

 3 6 1 6

 (9a) C 1 -C alkenyl group,

 2 6

 (10a) a halo C -C alkenyl group,

 2 6

 (11a) C -C anolenoquinole group,

 2 6

 (12a) a halo C -C alkynyl group,

 2 6

 (13a) C-C alkoxy C-C alkyl group,

 1 6 1 6

 (14a) a halo C-C alkoxy C-C alkyl group,

 1 6 1 6

 (15a) C-C alkoxy C-C alkoxy C-C alkyl group

 1 6 1 6 1 6

(16a) C 1 -C alkylthio C 1 -C alkyl group, (17a) a halo c -c al reio c -c anorequinole group,

 1 6 1 6

 (18a) c-canorequinole ;: norefienol c-canolore group,

 1 6 1 6

 (19a) Halo c -c al resulfiel C -C 1 ^ Norequinole ¾,

 1 6 1 6

 (20a) c -c anorequinole ;: norehoninole c -c anorequil group,

 1 6 1 6

 (21a) Halo C -c al resulfonyl c -c end, / Rekinole ¾,

 1 6 1 6

 (22a) a mono c-c al-noramino c-canolol 'group,

 1 6 1 6

 (23a) a di c -c arylamino c -c alkyl group which may be the same or different,

 1 6 1 6

 (24a) phenyl C 1 -C 7 'norecoxy c -C anorequinole group,

 1 6 1 6

 (25a) c -c anolenoquinolefluponyl group,

 1 6

 (26a) Halo C-c al ^ Nore 7 Nore Boninole ¾,

 1 6

 (27a) c -c alkoxy -C alkylcarbonyl group,

 1 6 1 6

 (28a) c -c alkoxy z canoleponinole group,

 1 6

 (29a) c -c alkoxy -C alkoxycal 7 i nyl group,

 1 6 1 6

 (30a) Halo C -c Arni! A xykanole poninole group,

 1 6

 (31a) c -c carbonyl carbonyl group,

 1 6

 (32a) mono-c-c-alaminocarbonyl group,

 1 6

 (33a) a di c -c arylaminocarbonyl group which may be the same or different,

 1 6

 (34a) c -c alkoxy z carbonyl c -c alkyl group,

 1 6 1 6

 (35a) c -canolenoquinole ;: sulfonyl group,

 1 6

 (36a) Halo c -c al ^ Noles Nore Honinole ¾,

 1 6

 (37a) Siano c-c al'kill group,

 1 6

(38a) phenyl C-C 7 'norequinole ¾,

 1 6

 (39a) Same or different

 (a) halogen atom, (b) cyano group, (c) nitro group, (d) C 1 -C alkyl group, (e) halo C 2 -Ca

 1 6 1 6 Lucinole group, (f) C-C alkoxy group, (g) Halo C-C alkoxy group, (h) C-C alkyl group

 1 6 1 6 1 6o group, (i) Halo C-C alkylthio group, (j) C-C alkylsulfinyl group, (k) Halo C-C

 1 6 1 6 1 Alkylsulfier group, (1) C 1 -C alkylsulfonyl group, (m) Halo C 1 -C alkyls

6 1 6 1 6 sulfonyl group, (n) mono-C-Canolenoquinamino group, (0) di-C-C-a may be the same or different Rualkylamino group and (p) c -c alkoxycarbonyl group

 1 6

A substituted phenyl C 1 -C alkyl group having one or more substituents on the ring selected from

 1 6

 (40a) a phenoxycarbonyl group,

(41a) Same or different

 (a) halogen atom, (b) cyano group, (c) nitro group, (d) C 1 -C alkyl group, (e) halo C 2 -Ca

 1 6 1 6 alkyl group, (f) C-C alkoxy group, (g) halo C-C alkoxy group, (h) C-C alkyl group

 1 6 1 6 1 6o group, (i) Halo C-C alkylthio group, (j) C-C alkylsulfinyl group, (k) Halo C-C

 1 6 1 6 1 Alkylsulfier group, (1) C 1 -C alkylsulfonyl group, (m) Halo C 1 -C alkyls

6 1 6 1 6 sulfonyl group, (n) mono-C-Canolenoquinamino group, (0) di-C-C-a may be the same or different

 1 6 1 6 alkylamino group and (p) c -c alkoxycarbonyl group

 1 6

A substituted phenoxycarbonyl group having one or more substituents selected on the ring,

(42a) phenylsulfonyl group,

(43a) Same or different

 (a) halogen atom, (b) cyano group, (c) nitro group, (d) C 1 -C alkyl group, (e) halo C 2 -Ca

 1 6 1 6 alkyl group, (f) C-C alkoxy group, (g) halo C-C alkoxy group, (h) C-C alkyl group

 1 6 1 6 1 6o group, (i) Halo C-C alkylthio group, (j) C-C alkylsulfinyl group, (k) Halo C-C

 1 6 1 6 1 Alkylsulfier group, (1) C 1 -C alkylsulfonyl group, (m) Halo C 1 -C alkyls

6 1 6 1 6 sulfonyl group, (n) mono-C-Canolenoquinamino group, (0) di-C-C-a may be the same or different

 1 6 1 6 alkylamino group and (p) c -c alkoxycarbonyl group

 1 6

A substituted phenylsulfonyl group having one or more substituents selected on the ring,

(44a) a di-C 6 -C anorequinolephosphono group which may be the same or different,

 1 6

 (45a) a di-C 6 -C anorequinolephosphonothio group which may be the same or different,

 1 6

 (46a) N-C-C alkyl-N-C-C alkoxycarbonylaminothio group,

 1 6 1 6

 (47a) N-C 1 -C alkyl- N-C _C alkoxycarbonyl C _C alkylaminothio group

 1 6 1 6 1 6

(48a) a di-C 6 -C alkylaminothio group which may be the same or different,

 1 6

 (49a) C 1 -C cycloalkylcarbonyl group,

 3 6

(50a) C 1 -C alkyl C 1 -C cycloalkylcarbonyl group, (51a) phenyl C 1 -C cycloalkylcarbonyl group,

 3 6

 (52a) Same or different

 (a) halogen atom, (b) cyano group, (c) nitro group, (d) C 1 -C alkyl group, (e) halo C 2 -Ca

 1 6 1 6 alkyl group, (f) C-C alkoxy group, (g) halo C-C alkoxy group, (h) C-C alkyl group

 1 6 1 6 1 6o group, (i) Halo C-C alkylthio group, (j) C-C alkylsulfinyl group, (k) Halo C-C

 1 6 1 6 1 Alkylsulfier group, (1) C 1 -C alkylsulfonyl group, (m) Halo C 1 -C alkyls

6 1 6 1 6 sulfonyl group, (n) mono-C-Canolenoquinamino group, (0) di-C-C-a may be the same or different

 1 6 1 6 alkylamino group and (p) c -c alkoxycarbonyl group

 1 6

A substituted phenyl c-c cycloalkyl having one or more substituents on the phenyl ring selected from

 3 6 Norequinolecanoleboninole group,

 (53a) C 1 -C alkenyloxycarbonyl group,

 2 6

 (54a) phenyl C 1 -C alkoxycarbonyl group,

 1 6

 (55a) Same or different

 (a) halogen atom, (b) cyano group, (c) nitro group, (d) C 1 -C alkyl group, (e) halo C 2 -Ca

 1 6 1 6 alkyl group, (f) C-C alkoxy group, (g) halo C-C alkoxy group, (h) C-C alkyl group

 1 6 1 6 1 6o group, (i) Halo C-C alkylthio group, (j) C-C alkylsulfinyl group, (k) Halo C-C

 1 6 1 6 1 Alkylsulfier group, (1) C 1 -C alkylsulfonyl group, (m) Halo C 1 -C alkyls

6 1 6 1 6 sulfonyl group, (n) mono-C-Canolenoquinamino group, (0) di-C-C-a may be the same or different

 1 6 1 6 alkylamino group and (p) c -c alkoxycarbonyl group

 1 6

Substituted phenyl c-c alkoxycarbo having one or more substituents on the ring selected from

 1 6

Nyl group,

 (56a) a phenyl C 1 -C alkylcarbonyl group, or

 1 6

 (57a) Same or different

 (a) halogen atom, (b) cyano group, (c) nitro group, (d) C 1 -C alkyl group, (e) halo C 2 -Ca

 1 6 1 6 alkyl group, (f) C-C alkoxy group, (g) halo C-C alkoxy group, (h) C-C alkyl group

 1 6 1 6 1 6o group, (i) Halo C-C alkylthio group, (j) C-C alkylsulfinyl group, (k) Halo C-C

 1 6 1 6 1 Alkylsulfier group, (1) C 1 -C alkylsulfonyl group, (m) Halo C 1 -C alkyls

6 1 6 1 6 sulfonyl group, (n) mono-C-Canolenoquinamino group, (0) di-C-C-a may be the same or different Rualkylamino group and (p) C 1 -C alkoxycarbonyl group

 1 6

A substituted phenyl c-c alkylcarbohydrate having one or more substituents on the ring selected from

 1 6

Le group

Indicates.

R ² is

 (lb) hydrogen atom,

(2b) a halogen atom,

(3b) a C 1 -C alkyl group,

 1 6

 (4b) a halo C 1 -C alkyl group,

 1 6

 (5b) Cyan group,

 (6b) a hydroxy group,

 (7b) C 1 -C anorecoxy group,

 1 6

 (8b) Halo C 1 -C anorecoxy group,

 1 6

 (9b) C-C alkoxy C-C alkoxy group,

 1 6 1 3

 (10b) Halo C-C alkoxy C-C alkoxy group,

 1 6 1 3

 (lib) C 1 -C alkylthio C 1 -C alkoxy group,

 1 6 1 3

 (12b) a halo C -C alkylthio C -C alkoxy group,

 1 6 1 3

 (13b) C 1 -C alkylsulfinyl C 1 -C alkoxy group,

 1 6 1 3

 (14b) a halo C -C alkylsulfinyl C -C alkoxy group,

 1 6 1 3

 (15b) a C-C alkylsulfonyl C-C alkoxy group,

 1 6 1 3

 (16b) a halo C-C alkylsulfonyl C-C alkoxy group,

 1 6 1 3

 (17b) mono C-C alkylamino C-C alkoxy group,

 1 6 1 3

 (18b) di C 1 -C alkylamino C 1 -C alkoxy groups which may be the same or different,

 1 6 1 3

 (19b) c -c alkylthio group,

 1 6

 (20b) a halo C -C alkylthio group,

 1 6

 (21b) C 1 -C alkylsulfier group,

 1 6

 (22b) a halo C 1 -C alkylsulfinyl group,

 1 6

(23b) C 1 -C alkylsulfonyl group, (24b) a halo C -C alkylsulfonyl group,

 1 6

 (25b) an amino group,

 (26b) mono C 1 -C alkylamino group,

 1 6

 (27b) a di-C 1 -C alkylamino group which may be the same or different,

 1 6

(28b) a phenoxy group,

 (29b) Same or different

 (a) halogen atom, (b) cyano group, (c) nitro group, (d) C 1 -C alkyl group, (e) halo C 2 -Ca

 1 6 1 6 alkyl group, (f) C-C alkoxy group, (g) halo C-C alkoxy group, (h) C-C alkyl group

 1 6 1 6 1 6o group, (i) Halo C-C alkylthio group, (j) C-C alkylsulfinyl group, (k) Halo C-C

 1 6 1 6 1 Alkylsulfier group, (1) C 1 -C alkylsulfonyl group, (m) Halo C 1 -C alkyls

6 1 6 1 6 sulfonyl group, (n) mono-C-Canolenoquinamino group, (0) di-C-C-a may be the same or different

 1 6 1 6 alkylamino group and (p) c -c alkoxycarbonyl group

 1 6

A substituted phenoxy group having one or more substituents selected from

 (30b) a phenylthio group,

 (31b) Same or different

 (a) halogen atom, (b) cyano group, (c) nitro group, (d) C 1 -C alkyl group, (e) halo C 2 -Ca

 1 6 1 6 alkyl group, (f) C-C alkoxy group, (g) halo C-C alkoxy group, (h) C-C alkyl group

 1 6 1 6 1 6o group, (i) Halo C-C alkylthio group, (j) C-C alkylsulfinyl group, (k) Halo C-C

 1 6 1 6 1 Alkylsulfier group, (1) C 1 -C alkylsulfonyl group, (m) Halo C 1 -C alkyls

6 1 6 1 6 sulfonyl group, (n) mono-C-Canolenoquinamino group, (0) di-C-C-a may be the same or different

 1 6 1 6 alkylamino group and (p) c -c alkoxycarbonyl group

 1 6

A substituted phenylthio group having one or more substituents selected from

(32b) phenylsulfier group,

(33b) Same or different

 (a) halogen atom, (b) cyano group, (c) nitro group, (d) C 1 -C alkyl group, (e) halo C 2 -Ca

 1 6 1 6 alkyl group, (f) C-C alkoxy group, (g) halo C-C alkoxy group, (h) C-C alkyl group

 1 6 1 6 1 6o group, (i) Halo C-C alkylthio group, (j) C-C alkylsulfinyl group, (k) Halo C-C

1 6 1 6 1 Alkylsulfier group, (1) C 1 -C alkylsulfonyl group, (m) Halo C 1 -C alkyls A sulfonyl group, (n) a mono-C-Canolenoquinolamino group, (0) di-C-C-a which may be the same or different

1 6 1 6 alkylamino group and (p) c -c alkoxycarbonyl group

 1 6

A substituted phenylsulfinyl group having one or more substituents selected on the ring,

(34b) a phenylsulfonyl group,

(35b) Same or different

 (a) halogen atom, (b) cyano group, (c) nitro group, (d) C 1 -C alkyl group, (e) halo C 2 -Ca

 1 6 1 6 alkyl group, (f) C-C alkoxy group, (g) halo C-C alkoxy group, (h) C-C alkyl group

 1 6 1 6 1 6o group, (i) Halo C-C alkylthio group, (j) C-C alkylsulfinyl group, (k) Halo C-C

 1 6 1 6 1 Alkylsulfier group, (1) C 1 -C alkylsulfonyl group, (m) Halo C 1 -C alkyls

6 1 6 1 6 sulfonyl group, (n) mono-C-Canolenoquinamino group, (0) di-C-C-a may be the same or different

 1 6 1 6 alkylamino group and (p) c -c alkoxycarbonyl group

 1 6

A substituted phenylsulfonyl group having one or more substituents selected on the ring,

(36b) a phenyl C-C alkoxy group, or

 1 6

 (37b) Same or different

 (a) halogen atom, (b) cyano group, (c) nitro group, (d) C 1 -C alkyl group, (e) halo C 2 -Ca

 1 6 1 6 alkyl group, (f) C-C alkoxy group, (g) halo C-C alkoxy group, (h) C-C alkyl group

 1 6 1 6 1 6o group, (i) Halo C-C alkylthio group, (j) C-C alkylsulfinyl group, (k) Halo C-C

 1 6 1 6 1 Alkylsulfier group, (1) C 1 -C alkylsulfonyl group, (m) Halo C 1 -C alkyls

6 1 6 1 6 sulfonyl group, (n) mono-C-Canolenoquinamino group, (0) di-C-C-a may be the same or different

 1 6 1 6 alkylamino group and (p) c -c alkoxycarbonyl group

 1 6

A substituted phenyl c-c alkoxy group having one or more substituents selected from the group

 1 6

Indicates.

 G is

 (lc) C 1 -C alkyl group,

 1 10

 (2c) a halo C 1 -C alkyl group,

 1 10

 (3c) C 1 -C alkenyl group,

 3 10

 (4c) a halo C 1 -C alkenyl group,

 3 10

(5c) C 1 -C alkynyl group, (6c) Halo C 1 -C alkynyl group,

 3 10

 (7c) C 1 -C cycloalkyl group,

 3 10

 (8c) Same or different

 (a) a halogen atom, (b) a C 1 -C anorequinole group, and (c) a halo C 1 -C alkyl group

 1 6 1 6

 A substituted c cycloalkyl group having one or more substituents selected from

 3 -c 10

 (9c) C 1 -C cycloalkenyl group,

 3 10

 (10c) Same or different

 (a) a halogen atom, (b) a C 1 -C anorequinole group, and (c) a halo C 1 -C alkyl group

 1 6 1 6

 A substituted c cycloalkenyl group having one or more substituents selected from

 3 -c 10

 (11c) C 1 -C cycloalkyl C 1 -C anorequinole group, or

 3 8 1 6

 (12c) Halo C-C cycloalkyl C-C alkyl group

 3 8 1 6

 Indicates.

 [0012] Z represents an oxygen atom or a sulfur atom.

 n represents an integer of 0 to 3.

 X may be the same or different

 (Id) a halogen atom,

 (2d) Cyan group,

 (3d) a nitro group,

 (4d) a C 1 -C alkyl group, or

 1 6

 (5d) Halo C 1 -C alkyl group

 1 6

 Indicates.

 [0013] m represents an integer of 0 to 4.

 Y can be the same or different

 (le) a halogen atom,

 (2e) Cyan group,

 (3e) a nitro group,

 (4e) hydroxyl group,

(5e) a mercapto group, (6e) an amino group,

 (7e) carboxyl group,

 (8e) a C 1 -C alkyl group,

 1 6

 (9e) Halo C 1 -C alkyl group

 (10e) c -c alkenyl group,

 2 6

 (l ie) a halo C-C alkenyl group,

 2 6

 (12e) c -c alkynyl group,

 2 6

 (13e) a halo c 2 -c alkynyl group,

 6

 (14e) Birds that may be the same or different C

 1 -C 7 'Lukil Sil 6 c 2-

(15e) phenyl C-C alkynyl group,

 2 6

 (16e) c 1 -c alkoxy

 6 c 1 -c alkoxy C — C alkyl group,

 6 L 6

 (17e) a hydroxy c-C alkyl group,

 1 6

 (18e) C-C alkylcarbonyloxy C-C alkino'le group,

1 6 1 6

 (19e) c 3 -c cycloalkyl group,

 6

 (20e) a halo c3-c cycloalkyl group,

 6

 (21e) c 3 -c cycloalkyl

 6 c 1 -c alkyl z group,

 6

 (22e) Halo c -c cycloalkyl

 6 C 1 -C ano I kill group,

3 6

 (23e) C-C anorecoxy group,

 1 6

 (24e) a halo-canoloxy group,

 1 -c 6

 (25e) c -c alkoxy c -c alkoxy group,

 1 6 1 6

 (26e) halo c -c alkoxy c 1 -c alkoxy group,

 1 6 6

 (27e) phenyl C-C alkoxy group,

 1 6

 (28e) C-C alkoxy C-C alkyl group,

 1 6 1 6

 (29e) halo c 1 -c

 6 c 1 -cano

 6

 (30e) c -c alkylthio group,

 1 6

 (31e) a halo c alkylthio group,

 1 -c 6

 (32e) C 1 -C alkylsulfier group,

 1 6

(33e) a halo c-c alkylsulfinyl group, (34e) C 1 -C alkylsulfonyl group,

 1 6

 (35e) a halo C-C alkylsulfonyl group,

 1 6

 (36e) C 1 -C alkylthio C 1 -C alkyl group,

 1 6 1 6

 (37e) a halo C 1 -C alkylthio C 1 -C alkyl group,

 1 6 1 6

 (38e) C-C alkylsulfinyl C-C alkyl group,

 1 6 1 6

 (39e) a halo C 1 -C alkylsulfinyl C 1 -C alkyl group,

 1 6 1 6

 (40e) C 1 -C alkylsulfonyl C 1 -C alkyl group,

 1 6 1 6

 (41e) a halo C -C alkylsulfonyl C -C alkyl group,

 1 6 1 6

 (42e) mono C 1 -C alkylamino group,

 1 6

 (43e) diC 1 -C alkylamino groups which may be the same or different,

 1 6

 (44e) phenylamino group,

 (45e) mono C-C alkylamino C-C alkyl group,

 1 6 1 6

 (46e) diC 1 -C alkylamino C 1 -C alkyl group which may be the same or different,

 1 6 1 6

(47e) phenyl group,

 (48e) Same or different

 (a) halogen atom, (b) cyano group, (c) nitro group, (d) C 1 -C alkyl group, (e) halo C 2 -Ca

 1 6 1 6 alkyl group, (f) C-C alkoxy group, (g) halo C-C alkoxy group, (h) C-C alkyl group

 1 6 1 6 1 6o group, (i) Halo C-C alkylthio group, (j) C-C alkylsulfinyl group, (k) Halo C-C

 1 6 1 6 1 Alkylsulfier group, (1) C 1 -C alkylsulfonyl group, (m) Halo C 1 -C alkyls

6 1 6 1 6 sulfonyl group, (n) mono-C-Canolenoquinamino group, (0) di-C-C-a may be the same or different

 1 6 1 6 alkylamino group and (p) c -c alkoxycarbonyl group

 1 6

A substituted phenyl group having one or more substituents selected on the ring,

 (49e) a phenoxy group,

 (50e) Same or different

 (a) halogen atom, (b) cyano group, (c) nitro group, (d) C 1 -C alkyl group, (e) halo C 2 -Ca

 1 6 1 6 alkyl group, (f) C-C alkoxy group, (g) halo C-C alkoxy group, (h) C-C alkyl group

 1 6 1 6 1 6o group, (i) Halo C-C alkylthio group, (j) C-C alkylsulfinyl group, (k) Halo C-C

1 6 1 6 1 Alkylsulfier group, (1) C 1 -C alkylsulfonyl group, (m) Halo C 1 -C alkyls A sulfonyl group, (n) a mono-C-Canolenoquinolamino group, (0) di-C-C-a which may be the same or different

 1 6 1 6 alkylamino group and (p) c -c alkoxycarbonyl group

 1 6

 A substituted phenoxy group having one or more substituents selected from

 (51e) a heterocyclic group, or

 (52e) Same or different

 (a) halogen atom, (b) cyano group, (c) nitro group, (d) C 1 -C alkyl group, (e) halo C 2 -Ca

 1 6 1 6 alkyl group, (f) C-C alkoxy group, (g) halo C-C alkoxy group, (h) C-C alkyl group

 1 6 1 6 1 6o group, (i) Halo C-C alkylthio group, (j) C-C alkylsulfinyl group, (k) Halo C-C

 1 6 1 6 1 Alkylsulfier group, (1) C 1 -C alkylsulfonyl group, (m) Halo C 1 -C alkyls

6 1 6 1 6 sulfonyl group, (n) mono-C-Canolenoquinamino group, (0) di-C-C-a may be the same or different

 1 6 1 6 alkylamino group and (p) c -c alkoxycarbonyl group

 1 6

 A substituted heterocyclic group having one or more substituents selected from: on the ring. Or

 (53e) Two adjacent Y's on the pyridine ring can be joined together to form a condensed ring, which can be the same or different

 (a) halogen atom, (b) cyano group, (c) nitro group, (d) C 1 -C alkyl group, (e) halo C 2 -Ca

 1 6 1 6 alkyl group, (f) C-C alkoxy group, (g) halo C-C alkoxy group, (h) C-C alkyl group

 1 6 1 6 1 6o group, (i) Halo C-C alkylthio group, (j) C-C alkylsulfinyl group, (k) Halo C-C

 1 6 1 6 1 Alkylsulfier group, (1) C 1 -C alkylsulfonyl group, (m) Halo C 1 -C alkyls

6 1 6 1 6 sulfonyl group, (n) mono-C-Canolenoquinamino group, (0) di-C-C-a may be the same or different

 1 6 1 6 alkylamino group and (p) c -c alkoxycarbonyl group

 1 6

 One or more substituents selected on the ring can also be present on the ring. }

 The substituted pyridinecarboxylic acid anilide derivative represented by the above and its salts, an agricultural and horticultural agent comprising the compound as an effective component, and a method of using the same.

 The invention's effect

 [0015] According to the present invention, it is possible to provide agricultural and horticultural agents, particularly insecticides and acaricides, which have superior performance as compared to the prior art.

 BEST MODE FOR CARRYING OUT THE INVENTION

[0016] In the definition of the general formula (I) of the substituted pyridinecarboxylic acid anilide derivative of the present invention, "Noguchi", "C-C alkyl", "c-c alkoxy", "c-C canolekenyl" in substituents

 1 6 1 6 2 6

 , “C-c alkynyl”, “heterocyclic group” and the like have the following meanings.

 2 6

 “Haguchi” or “halogen atom” refers to a chlorine atom, a bromine atom, an iodine atom or a fluorine atom.

 [0017] "C 1 -C alkyl" refers to a linear or branched alkyl having 1 to 6 carbon atoms.

 1 6

 , For example, methinore, ethinore, n-propinole, i-propinore, n-butinore, i-butinole, s-butinore, t-butinore, n-pentinore, isopentinole, neopentinole, t-pentinole, 2-methylbutyl, n-hexyl, 2-hexyl Ethylbutyl, 1,2,2-trimethylpropyl and the like.

[0018] "C_C alkyl" refers to a linear or branched alkyl having 1 to 10 carbon atoms;

 1 10

 And, for example, methylol, ethyl, n-propyl, i-propyl, nbutyl, i-butyl, s-butinole, t-butinole, n pentinore, isopentinole, neopentinole, t-pentinole, 2-methylbutyl, n-hexyl, 2-ethylbutyl 1, 2, 2-trimethylpropyl, 1-ethinorepropinore, n-heptinole, n-octinore, 2-ethinorehexinore, n-noninore, n-decyl and the like.

“C 1 -C cycloalkyl” refers to a cyclic alkyl having 3 to 6 carbon atoms, for example,

 3 6

 , Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like.

 [0020] "C 1 -C cycloalkyl" refers to a cyclic alkyl having 3 to 8 carbon atoms, for example,

 3 8

 , Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl and the like.

 [0021] "C 1 -C cycloalkyl" refers to a cyclic alkyl having 3 to 10 carbon atoms;

 3 10

 Examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl, cyclodecyl and the like.

 [0022] "C_C cycloalkenyl" refers to cyclic alkenyl having 3 to 10 carbon atoms,

 3 10

 For example, cyclopropeninore, cyclobuteninore, cyclopenteninole, cyclohexenore, cyclotatur, cyclodecenyl and the like can be mentioned.

 [0023] "C 1 -C alkoxy" is an alkyl moiety having 1 straight or branched carbon atoms.

 13

Represents alkoxy, which is ~ 3 alkyls, for example, methoxy, ethoxy, propoxy, i Examples include sopropoxy.

[0024] "C 1 -C alkoxy" is an alkoxy whose alkyl moiety is the above "C 1 -C alkyl".

 1 6 1 6

 For example, methoxy, ethoxy, propoxy, butoxy, isobutoxy, t-butoxy

, Pentyloxy, hexyloxy and the like.

 [0025] "C 1 -C alkenyl" refers to a straight or branched chain having at least one double bond

 2 6

 Represents alkenyl having 2 to 6 carbon atoms, for example, bulle, 1 propenyl, allyl, 1-butur, 2 butur, 3 butur, 2 pentul, 2 methyl-1 propenyl, 2, 4 pentagenil, 3 Xenyl and the like.

[0026] "C_C alkenyl" refers to a linear or branched chain having at least one double bond

 3 10

 Alkenyl having 3 to 10 carbon atoms, for example, 1-butur, 2 butur, 3 —butur, 2 pentul, 2,4 pentagenyl, 3 hexenyl, 3 heptenyl, 3 —octatur, 3—nonenole, 3-decenyl etc. are mentioned.

[0027] "C 1 -C alkynyl" is a straight chain or branched chain having at least one triple bond

 2 6

 Alkynyl having 2 to 6 carbon atoms, such as Etul, 2-Probule, 1-Butul, 2 Butur, 3 Butur, 2 Pentur, 3 Hexhur, etc.

[0028] "C_C alkynyl" is a straight or branched chain having at least one triple bond.

 3 10

 An alkynyl having 3 to 10 carbon atoms is exemplified, and examples thereof include 1-buturur, 2 butur, 3-butur, 2 pentur, 3 hexul, 3 heptul, 3-otatul, 3-nonynyl, 3-decynyl and the like.

[0029] In addition, numbers such as “C 1 -C:” and “C 2 -C” are carbon such as 2 to 6 carbon atoms, 3 to 10 carbon atoms, etc.

 2 6 3 10

 Indicates the range of the number of atoms.

 Further, the above definition can be given for a group to which the above substituent is linked. For example, in the case of “halo c-c alkyl”, one or more halogen atoms which may be the same or different

1 6

 A substituted linear or branched carbon atom;! To 6 alkyl groups, for example, difluoromethyl, trifluoromethyl, 2, 2, 2-trifluoroethyl, perfluorinated hexyl, etc. Can be mentioned.

[0030] "Heterocyclic group" means one or more heter selected from an oxygen atom, a sulfur atom and a nitrogen atom. A 5- or 6-membered heterocyclic group having a mouth atom, such as pyridyl group, pyridine N oxide group, pyrimidinyl group, furyl group, tetrahydrofuryl group, chenyl group, tetrahydrophenyl group, tetrahydrobilanyl group, tetrahydro Examples include thiopyranyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, imidazolyl group, triazolyl group, pyrazolyl group and the like.

 Examples of the “fused ring” include naphthalene, tetrahydronaphthalene, indene, indane, quinoline, quinazoline, indanol, indoline, chroman, isochroman, benzodioxan, benzodioxanol, benzofuran, dihydrobenzofuran, benzothiophene, dihydrin benzothiophene, Benzoxazonore, benzothiazonole, benzimidazole, indazole and the like.

 Of the general formula (I) of the substituted pyridinecarboxylic acid anilide derivative of the present invention,

R ¹ is preferably (la) a hydrogen atom, (2a) a C_C alkyl group, (3a) a halo C 1 -C alkyl group

 1 6 1 6

(4a) C 1 -C alkylcarbonyl C 2 -C alkyl group, (9a) C _C alkenyl group, (10a)

1 6 1 6 2 6

, C -C alkenyl group, (11a) C -C alkynyl group, (12a) Halo C -C alkynyl group, (

2 6 2 6 2 6

 13a) C 1 -C alkoxy C 1 -C alkyl group, (14a) Halo C 1 -C alkoxy C 1 -C alkyl group

1 6 1 6 1 6 1 6 group, (15a) C-C alkoxy C-C alkoxy C-C alkyl group, (25a) C-C alkyl

 1 6 1 6 1 6 1 6 Carbonyl group, (26a) Halo C 1 -C alkylcarbonyl group, (27a) C _C alkoxy C _C

 1 6 1 6 1 6 Alkylcarbonyl group, (28a) C 1 -C alkoxycarbonyl group, (30a) Halo C 1 -C al

 1 6 1 6 Coxycarbonyl group, (34a) C 1 -C alkoxycarbonyl C 1 -C alkyl group, (37a)

 1 6 1 6

C-C alkyl group, (38a) phenyl C-C alkyl group, (39a) may be the same or different

1 6 1 6

, _(A) a halogen atom, (b) a Shiano group, (c) nitro group, (d) C -C alkyl group, (e) halo C -C §

 1 6 1 6 Noreki group, (f) C-C alkoxy group, (g) Halo C-C alkoxy group, (h) C-C alkyl group

 1 6 1 6 1 6

(I) Halo C 1 -C alkylthio group, 0) C 1 -C alkyl sulfier group, (k) Halo C 1 -C

 1 6 1 6 1 Alkylsulfier group, (1) C 1 -C alkylsulfonyl group, (m) Neuro C 1 -C alkyls

6 1 6 1 6 sulfonyl group, ( _n ) mono C 1 -C anoleno quinolamino group, (0) di-C 1 -C 6, which may be the same or different

 1 6 1 6 one or more substitutions selected from alkylamino groups and (p) c -c alkoxycarbonyl groups

 1 6

Substituted phenyl C 1 -C alkyl groups having a group on the ring, (40a) phenoxycarbonyl group, (4

 1 6

la) may be the same or different (a) halogen atom, (b) cyano group, (c) nitro group, (d) C -C Alkynole group, ( _e ) halo C-C canolequinole group, (f) C-C alkoxy group, (g) halo C-C alco

1 6 1 6 1 6 Xyl group, (h) C-C alkylthio group, (i) Halo C-C alkylthio group, (j) C-C anololyl

 1 6 1 6 1 6 Sulfinyl group, (k) Halo C-C alkyl sulfinyl group, (1) C-C alkyl sulfoni group

 1 6 1 6

(M) a halo C 1 -C alkylsulfonyl group, (n) a mono C 1 -C anolenoquinamino group, (o) the same

 1 6 1 6

One or different di-C-C canolequinoleamino groups, and (p) C-C alkoxycarbonyl

 1 6 1 6

A substituted phenoxycarbonyl group having one or more substituents selected from the above group on the ring, or (49a) a C 2 -C cycloalkylcarbonyl group, more preferably (la) a hydrogen atom, (2a

 3 6

 ) C-C canolequinole group, (13a) C-C canolecoxy group C-C canorequinole group, (25a) C-C canolequinol group

1 6 1 6 1 6 1 6 Carbonyl group, (27a) C 1 -C alkoxy C 1 -C alkylcarbonyl group, (28a) C _C al

 1 6 1 6 1 6 Coxoxycarbonyl, (37a) Ciano C 1 -C canolequinole group, (49a) C _C cycloalkyl carbo

 1 6 3 6

Ninole group, (50a) C 1 -C alkyl C 1 -C cycloalkylcarbonyl group, (51a) phenyl C-

1 6 3 6 3

C cycloalkylcarbonyl group, (52a) same or different (a) halogen atom, (b

6

 ) Cyano group, (c) Nitro group, (d) C 1 -C anolenoquino group, (e) Halo C 1 -C anorequinole group, (f) C _C a

1 6 1 6 1 6 Lucoxy group, ( _g ) halo c-C alkoxy group, (h) C-C alkylthio group, (i) halo C-C

 1 6 1 6 1 6 Norekiruthio group, (j) c -c alkylsulfinyl group, (k) halo c -c alkylsulfinyl group

 1 6 1 6 nore group, (1) C 1 -C alkylsulfonyl group, (m) halo C 1 -C alkylsulfonyl group, (n)

 1 6 1 6

C-Canolenoquinamino groups, (0) di-C-Canolenoquinamino groups which may be the same or different, and

1 6 1 6

(P) one or more substituents selected from C 1 -C alkoxycarbonyl groups on the phenyl ring

1 6

Substituted phenyl C 1 -C cycloalkylcarbonyl group, (53a) C 1 -C alkenyl

 3 6 2 6

Xyloxycarbonyl group, (54a) phenyl C 1 -C alkoxycarbonyl group, (55a) same or different

 1 6

(A) halogen atom, (b) cyano group, (c) nitro group, (d) C 1 -C alkyl group, (e)

 1 6

C, C alkyl group, (i) C-C alkoxy group, (g) halo C-C alkoxy group, (h) C-C

 1 6 1 6 1 6 1 alkylthio group, (i) halo c-c alkylthio group, (j) c-c alkylsulfier group, (

6 1 6 1 6

k) No, mouth C -C alkyl sulfier group, (1) C -C alkylsulfonyl group, (m) No, mouth C-

1 6 1 6 1

C alkylsulfonyl group, (n) mono C 1 -C anolenoquinamino group, (0) may be the same or different

6 1 6

A di-c-canolenoquinamino group and (p) c-c alkoxycarbonyl group 1

 1 6 1 6

A substituted phenyl C 1 -C alkoxycarbonyl group having the above substituents on the ring, (56a)

 1 6

Enyl C 1 -C alkylcarbonyl group, or (57a) same or different (a) halogen (B) cyano group, (c) nitro group, (d) C 1 -C alkyl group, (e) halo C 1 -C alkyl group,

 1 6 1 6

 (i) C-C alkoxy group, (g) halo C-C alkoxy group, (h) C-C alkylthio group, (i) no

1 6 1 6 1 6

 Mouth C-C alkylthio group, (j) C-C alkylsulfinyl group, (k) halo C-C alkynole

1 6 1 6 1 6 Sulfiel group, (1) C 1 -C alkylsulfonyl group, (m) Halo C 1 -C alkylsulfonyl group

 1 6 1 6

 A group, (n) a mono-C-Canolenoquinamino group, (0) a di-C-C alkyla which may be the same or different

 1 6 1 6

 Mino group, and (p) one or more substituents selected from C 1 -C alkoxycarbonyl groups on the ring

 1 6

 A substituted phenyl c -c alkylcarbonyl group having

 1 6

 More preferably (la) a hydrogen atom, (2a) a C_C alkyl group, (3a) a halo C-C alkyl group, (

 1 6 1 6

 4a) C 1 -C alkylcarbonyl C 2 -C alkyl group, (9a) C _C alkenyl group, (10a) halo

1 6 1 6 2 6

 C 1 -C alkenyl group, (11a) C 1 -C alkynyl group, (12a) Halo C 1 -C alkynyl group, (13a)

2 6 2 6 2 6

 C-C alkoxy C-C alkyl group, (14a) halo C-C alkoxy C-C alkyl group, (1

1 6 1 6 1 6 1 6

 5a) C 1 -C alkoxy C 1 -C alkoxy C 1 -C alkyl group, (25a) C 1 -C alkyl carbo

1 6 1 6 1 6 1 6 Nyl group, (26a) Halo C 1 -C alkylcarbonyl group, (27a) C _C alkoxy C _C alkyl

 1 6 1 6 1 6 Norecanolenobonole group, (28a) C-C alkoxycarbonyl group, (30a) Halo C-C alkoxy force

 1 6 1 6

 Norebonyl group, (37a) Ciano C 1 -C alkyl group, or (49a) C _C cycloalkylcarbohydrate

 1 6 3 6

 More preferably (la) a hydrogen atom, (2a) a C_C alkyl group, (13a) a C_C

 1 6 1 6 Norrecoxy C 1 -C alkyl group, (25a) C 1 -C alkylcarbonyl group, (27a) C _C alkoxy

 1 6 1 6 1 6 Si C -C alkylcarbonyl group, (28a) C 1 -C alkoxycarbonyl, (37a) Cyan C-

1 6 1 6 1

A C alkyl group, or (49a) a C 1 -C cycloalkylcarbonyl group.

 6 3 6

[0032] R ² is preferably (lb) a hydrogen atom, (2b) a halogen atom, (3b) a C_C alkyl group, (4b)

 1 6

 C, C alkyl group, (6b) hydroxy group, (7b) C-C alkoxy group, (8b) halo C-C

1 6 1 6 1 6 Norrecoxy group, (%) C-C alkoxy C-C alkoxy group, or (10b) Halo C-C alkoxy

 1 6 1 3 1 6 Xoxy C 1 -C alkoxy group, more preferably (lb) hydrogen atom, (2b) halogen atom,

13

 (7b) is a C 1 -C alkoxy group.

 1 6

 [0033] G is preferably (lc) C 1 -C alkyl group, (2c) halo C 1 -C alkyl group, (7c) C 1 -C

 1 10 1 10 3 10Cycloalkyl group, or (11c) C 1 -C cycloalkyl C 1 -C alkenoquinole group, more preferred

 3 8 1 6

Or (lc) C -C alkyl group _c

 Ten

[0034] X is preferably (Id) a halogen atom, or (4d) a C 1 -C alkyl group, and more preferably Or X means no substitution, and n is 0.

[0035] Y is preferably (le) a halogen atom, (8e) C _C canolequinole group, (9e) halo C -C alkyl

 1 6 1 6 group, (23e) C 1 -C alkoxy group, (24e) halo C 1 -C alkoxy group, (30e) C _C anoalkyl

 1 6 1 6 1 6 thio group, or (31e) halo C 1 -C alkylthio group, more preferably (le) halogen atom

 1 6

 Child, (8e) C 1 -C ano quinole group, (9e) halo C 2 -C ano quinole group, (23e) C _C alkoxy group,

 1 6 1 6 1 6 is a (30e) C 1 -C alkylthio group.

 1 6

 m is preferably 1 or 2, and more preferably 1.

 Z is preferably an oxygen atom.

Examples of the salt of the substituted pyridinecarboxylic acid anilide derivative represented by the general formula (I) of the present invention include alkali metal (lithium, sodium, potassium, etc.) salts, alkaline earth metals (calcium, magnesium, etc.) Salts, ammonium salts, salts of organic amines (methylamine, triethylamine, diethanolamine, piperidine, pyridine, etc.) or acid addition salts. Acid addition salts include, for example, acetate, propionate, and salt. Acid salts, trifluoroacetates, benzoates and other carboxylates, methanesulfonate, trifluoromethanesulfonate, p sulfonates such as toluenesulfonate, hydrochloride, sulfate, nitrate, carbonate Examples include inorganic acid salts such as salts.

[0037] The substituted pyridinecarboxylic acid anilide derivative represented by the general formula (I) of the present invention may contain one or more asymmetric centers in the structural formula, and two or more optical isomers may be included. And diastereomers may exist, and the present invention includes all of the optical isomers and mixtures in which they are contained in an arbitrary ratio. In addition, the substituted pyridinecarboxylic acid anilide derivative represented by the general formula (I) of the present invention may have two geometric isomers derived from a carbon-carbon double bond in the structural formula. The invention includes all of the various isomers and mixtures containing them in any proportion.

 [0038] The ability to represent a typical production method of the substituted pyridinecarboxylic acid anilide derivative represented by the general formula (I) of the present invention is not limited to these.

 Manufacturing method 1

[0039] [Chemical 2]

[0040]

 Group, halo c -canolenoquinole group, phenyl group, substituted phenyl group or phenyl c -c alkyl

1 6 1 4 group, W is — O, S or — N (R ⁴ )-(wherein R ⁴ is a hydrogen atom, C 1 -C alkyl)

 1 6 Kill group, halo c -canolenoquinol group, phenyl group, substituted phenyl group or phenyl c -c al

 1 6 1 4 Indicates a kill group. Q represents a halogen atom or a C 1 -C alkoxy group. )

 1 6

In the substituted pyridinecarboxylic acid anilide derivative represented by the general formula (I), Z is represented by an oxygen atom, R ² is a hydrogen atom, a fluorine atom or WR ³ (W and R ³ are the same as above. The substituted pyridinecarboxylic acid anilide derivative (I 2) represented by general formula (Π—1) to general formula (Π—3) and the pyridine carboxylate represented by general formula (III) By reacting an acid halide or pyridinecarboxylic acid ester in the presence or absence of a base in an inert solvent, or represented by general formula (Π—1) to general formula (Π—3) Forces that can be produced by reacting an aniline derivative and a pyridinecarboxylic acid represented by the general formula (IV) in the presence of a condensing agent in the presence or absence of a base in an inert solvent. If it ’s a manufacturing method, it ’s good.

[0042] The aniline derivative represented by the general formula (Π-2) is produced by reducing the aniline derivative represented by the general formula (II 1) in an inert solvent in the presence of a reducing agent. Can do. The aniline derivative represented by the general formula (Π-3) is represented by the general formula (V) in an inert solvent in the presence or absence of a base, the aniline derivative represented by the general formula (II 1). Produced by reacting with alcohol derivatives, thiol derivatives or amine derivatives Can do.

 [0043] General formula (II 1) → General formula (II 2)

 Reducing agents that can be used in this reaction include lithium metal hydride, lithium borohydride, sodium borohydride, diisobutylaluminum hydride, metal hydride such as sodium bis (2-methoxyethoxy) aluminum hydride, metal lithium The metal or metal salt, etc. can be exemplified, and the amount used can be appropriately selected from the range of equivalent to excess amount with respect to the ayurin derivative represented by the general formula (Π-1). .

 The inert solvent used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction, for example, aromatic hydrocarbons such as benzene, toluene and xylene, methyl chloride, chloroform, tetrachloride. Inert solvents such as halogenated hydrocarbons such as carbon, halogenated aromatic hydrocarbons such as black benzene and dichlorobenzene, and chain or cyclic ethers such as jetyl ether, dioxane and tetrahydrofuran (THF) These inert solvents can be used alone or in admixture of two or more. The reaction temperature can be from room temperature to the boiling point of the inert solvent to be used, and the reaction time is not constant depending on the reaction scale and reaction temperature, but may be in the range of several minutes to 50 hours. After completion of the reaction, it can be isolated from the reaction system containing the target product by a conventional method. The target product can be produced by recrystallization, column chromatography or the like, if necessary. Moreover, it is also possible to use for the next reaction process, without isolating a target object from a reaction system.

[0044] General formula (II 1) → General formula (II 3)

Bases that can be used in this reaction include metal hydrides such as lithium hydride, sodium hydride and lithium hydride, metal alcoholates such as sodium methoxide, sodium ethoxide and potassium t-butoxide, n-butyl lithium, and s-butyl. Examples thereof include alkyl metals such as lithium and t-butyllithium, and the amount used is appropriately selected from the range of equivalent to excess amount with respect to the aniline derivative represented by the general formula (Π-1). It ’s fine. The inert solvent used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction, for example, aromatic hydrocarbons such as benzene, toluene and xylene, alcohols such as methanol and ethanol, and jetyl. Illustrate inert solvents such as chain, cyclic ethers such as ether, 1,2-dimethoxyethane, dioxane, tetrahydrofuran, etc. These inert solvents can be used alone or in admixture of two or more. The reaction temperature can be in the range of 70 ° C to the boiling point of the inert solvent used, and the reaction time is not constant depending on the reaction scale and reaction temperature, but may be in the range of several minutes to 50 hours.

 After completion of the reaction, it can be isolated from the reaction system containing the target product by a conventional method. The target product can be produced by recrystallization, column chromatography or the like, if necessary. Moreover, it is also possible to use for the next reaction process, without isolating a target object from a reaction system.

[0045] General formula (Π—1), general formula (Π—2) or general formula (Π—3) → —general formula (I 2)

The condensing agent used in this reaction, for example cyanophosphonate Jechiru (DEPC), carboxymethyl sulfonyl diimidazole (CDI), 1, 3- dicyclo hexyl Cal positive imide (DCC), black hole carbonate esters, iodide _2-chloro 1 Examples include methylpyridinium and the like. Examples of the base used in this reaction include inorganic bases and organic bases. Examples of inorganic bases include hydroxides of alkali metal atoms such as sodium hydroxide and potassium hydroxide, sodium hydride, and potassium hydride. Alkali metal hydrides such as sodium ethoxide, potassium t-butoxide, etc., alkali metal salts such as sodium carbonate, potassium carbonate, sodium bicarbonate, etc., and organic bases include, for example, triethylamine, pyridine, DBU The amount used may be selected from the range of equimolar to excess molar relative to the pyridinecarboxylic acid derivative represented by the general formula (III) or (IV).

[0046] The inert solvent used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction, for example, aromatic hydrocarbons such as benzene, toluene and xylene, methyl chloride, and chloroform. , Halogenated hydrocarbons such as carbon tetrachloride, halogenated aromatic hydrocarbons such as black benzene and dichlorobenzene, chain or cyclic ethers such as jetyl ether, dioxane and tetrahydrofuran, and esters such as ethyl acetate , Amides such as dimethylformamide and dimethylacetamide, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone, and inert solvents such as acetone and methylethylketone. Solvents can be used alone or in combination of two or more. Since this reaction is an equimolar reaction, each reactant may be used in an equimolar amount, but any of the reactants can be used in excess, and the reaction temperature ranges from room temperature to the boiling point of the inert solvent used. The reaction time is not constant depending on the reaction scale and reaction temperature, but it may be carried out in the range of several minutes to 48 hours.

 After completion of the reaction, it can be isolated from the reaction system containing the target compound by a conventional method. If necessary, the target product can be produced by recrystallization, column chromatography, etc. An aniline derivative represented by a general formula (Π-1) can be produced according to the production method disclosed in JP-A-11-302233 or 2001-122836.

 [0047] In addition, pyridinecarboxylic acid derivatives represented by the general formula (III) or (IV) are known literatures (for example, Industrie Chimique Beige (1967), 32, 165, JP-A-03-52862, JP-A-03). — 81263, J. Chem. Soc., Perkin Trans I, 1984, 1501, etc.) It can be produced according to the method described.

 [0048] Manufacturing method 2

[0049] [Chemical 3]

 (1 -2) (1 -3)

[0050] (wherein R ¹ , R ² , G, X, Y, m and η are the same as above.)

 Among the substituted pyridinecarboxylic acid anilide derivatives represented by the general formula (I), the substituted pyridinecarboxylic acid anilide derivative (I 3) in which Ζ is a sulfur atom is an aniline derivative represented by (I 2). It can be produced by reacting with Lawesson's reagent according to a known method (Tetrahedron Lett., 21 (42), 4061 (1980)).

 [0051] Manufacturing method 3

[0052] [Chemical 4] Ym,

 (I -2a) (I -2)

[0053] ^{(wherein, R 2, G, X,} Y, Q, m and n are as defined above. R ¹ 'is the same comb in R ^1, provided that a hydrogen atom is excluded.)

Of the substituted pyridinecarboxylic acid anilide derivatives represented by the general formula (I), a substituted pyridinecarboxylic acid anilide derivative (I 2) other than R ¹ is a hydrogen atom is an amide derivative represented by the general formula (I 2a) It can be produced by reacting a halide derivative or ester derivative represented by the general formula (VI) in an inert solvent in the presence or absence of a base.

[0054] Bases that can be used in this reaction include metal hydrides such as lithium hydride, sodium hydride and lithium hydride, metal alcoholates such as sodium methoxide, sodium ethoxide and potassium t-butoxide, and n-butyllithium. , S butyl lithium, t butyl lithium and the like, and the use amount thereof is appropriately selected from the range of equivalent to excess amount with respect to the amide derivative represented by the general formula (I 2a). Use it. The inert solvent used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction, for example, aromatic hydrocarbons such as benzene, toluene and xylene, alcohols such as methanol and ethanol, and jetyl. Examples of the inert solvent include ethers, 1,2-dimethoxyethane, dioxane, tetrahydrofuran, and other chain or cyclic ethers. These inert solvents may be used alone or in combination of two or more. can do. The reaction temperature can be in the range of 70 ° C to the boiling point of the inert solvent used, and the reaction time is not constant depending on the reaction scale and reaction temperature, but may be in the range of several minutes to 50 hours.

 After completion of the reaction, it can be isolated from the reaction system containing the target product by a conventional method. If necessary, the target product can be produced by recrystallization, column chromatography, etc.

[0055] Production Method 4 [0056] [Chemical 5]

[0057] (where G,

X, n, Y and m are the same as above, and q is 1 or 2. )

 In addition, the substituted pyridinecarboxylic acid anilide derivative represented by the general formula (I-2c) is obtained by converting the sulfide derivative represented by the general formula (I 2b), which can be produced by the production method 1, with an oxidizing agent in the presence of an inert solvent. It can manufacture by making it react.

 Examples of the inert solvent used in this reaction include halogenated hydrocarbons such as methylene chloride and chloroform, aromatic hydrocarbons such as toluene and xylene, halogenated compounds such as fluorobenzene, chloroform benzene, and dichlorobenzene. Examples thereof include aromatic hydrocarbons, acids such as acetic acid, and alcohols such as methanol, ethanol and propanol. Examples of the oxidizing agent include metaclonal perbenzoic acid, peracetic acid, potassium metaperiodate, potassium hydrogen persulfate (Oxon (registered trademark)), hydrogen peroxide, and the like. The sulfur derivative represented by (I 2b) may be used by appropriately selecting from a range of 0.5 to 3 equivalents.

 The reaction time should be in the range of 50 ° C to the boiling point of the inert solvent used, but the reaction time is not constant depending on the reaction temperature, reaction scale, etc., but is in the range of several minutes to 24 hours. After completion of the reaction, the product can be isolated from the reaction system containing the product according to a conventional method. If necessary, the product can be produced by recrystallization, column chromatography or the like.

 [0058] Representative compounds of the substituted pyridinecarboxylic acid ureido derivatives represented by the general formula (I) are illustrated in Table 1, but the present invention is not limited thereto. In addition, the “physical properties” column in Table 1 describes the melting point (° C) or the refractive index [n (° C)], and the compound described as amorphous.

 D

Table ¹ shows the ¹ H-NMR data for. In the table, “n” is normal, “i-” is iso, “t-” is tertiary, “c-” is cyclo, “Me” is methyl, “Et” is ethyl. `` Pr '' is a propyl group, `` Bu '' is a butyl group, `` Pen '' is a pentyl group "Hex" is a hexyl group, "Ac" is a acetyl group, "l-Ph-c-Pr" is 1 phenol cyclopropyl group, "1-6.-?" Is 1-methyl. Indicates a leucyclopropyl group [Table 1-1]

 Table 1 O

 O

No. GY ¹ R 'R ² Physical properties

 1-1 i-Bu 2-Me H F 154.6-158.9

1-2 i-Bu 2-CI H F 175.6-175.7

1-3 i-Bu 2-OMe H F 121.4-123.7

1-4 i-Bu 2-CI CH ₂ OEt F 1.4909 (22.8)

1-5 i-Bu 2-Me F 1.4880 (25.0)

1-6 i-Bu 2-Me CO-t-Bu F 1.4872 (23.6)

1-7 n-Pen 2-Me H H 1.5213 (19 00.8)

1-8 i-Bu 2-Me H H 175-178

1-9 i-Bu 2-OMe H H 109-109.5

1-10 i-Bu 2-S e H H

1-11 i-Bu 2-CF ₃ HH 163-164

1-12 i-Bu 6-Me H H 120-124

1-13 i-Bu 4 Me H H 142-142.5

1-14 i-Bu 4-CF3 H H 131-133

1-15 i-Bu 2-F H H 124-125

1-16 i-Bu 2-CI H H 66-70

1-17 i-Bu H H H 118-119

1-18 i-Bu 2-C G 6- Me H H 114-118

1-19 i-Bu 2- e-6-CF ₃ HH 1.4872 (21.3)

 () ¾

 Ζ

I.690 / -00Zdf / X3d εΐm 忭 0 / 800Z ΟΛ Table 2

Agricultural and horticultural chemicals containing the substituted pyridinecarboxylic acid anilide derivative represented by the general formula (I) of the present invention or a salt thereof as an active ingredient, particularly agricultural and horticultural insecticides or acaricides are paddy rice, fruit trees and vegetables. It is suitable for various pests such as various forests, horticulture, storage pests, sanitary pests, nematodes, and other crops that damage crops and flowers. For example, Adoxophves orana fasciata and Chiyanokokakumon Adoxophyes sp., Linkoko Leguminivora glycinivorella, Olethreutes mori, Calop tilia thevivora, Apple sword (Caloptilia zachrysa), Phylionorycter stadium stamina ), White butterfly (Piers rapae crucivora), Tobacco moths (Heliothis sp.), Codling moth (Laspey resia pomonella), Pteras moth (Plutel la xylostella) Argyresthia conjugella, Carposina niponensis; Chilo suppressalis, Naphalocrocis medinahs, Ephestia elutelk, Glyphodes pyloalis (Scirpophaga incertulas), Parrotara guttata, Pseudoetia separata, Inesou (esamia inferens, No, Semonoto ¹ ) (^ podoptera litura), Spodoptera exigua, etc.

[0065] Futano Konnoi (Macrosteles fascifrons), Fritillaria (Nephotettix cincticeps), Tobirounka (Nilaparvata lugens), Cecil planta (Sogatella furcifera), Mikankifu (Diaphonna citn), Peur (Triaieurodes vaporariorum), Niseguikonafu ,, HM emissions (Lipapnis erysimi), Momono sword Zonofumun (Myzus persicae) _s Nonoro ¹ Nomun (and eroplast seudaonidia duplex ;, Nanmanorekai sword Fumun (and omstockaspis perniciosa, Noi, 7 Garamushi (Unaspis yanonensis), etc. Hemiptera pests (Anomala rufocuprea), Japanese beetle (Popilla japonica), Lasioderma serricorne, Buffalo (Lyctus brunneus), Ninyuyahosian (Callosobrucnus chinensis) Listroderes costirostris, Sitophilus zeamais, Anthonomus grandis granais, Lissornoptrus oryzophnus, Rein, Aulacophora femoralis, Oulema or Oulemayz Phyllotreta striolata)

 omicus piniperda), Korotofpoat heat nore (Leptinotarsa aecemlinei)

 Beetles, pests such as corn beetle (Epilachna varivestis), corn nolate worms (Diabrotica sp.),

[0066] Uno, Ye (Dacus (Zeugoaacus) cucurbitae), Canco no (Dacus (Bactrocera) dorsal is), Ineno, Mog U no (Agromyza oryzae), Onioninoqua (Delia antiqua), Tanenoe (D alia) platura), Diptera pests such as soybean flies, Asphondylis sp. semipenetr ans, Aphelenchus avenae, Roh, Aphelencho ides ritzemabosi, and other pests of the order, Mikanno, Panicchus citri, Apple, Panonychus ulmi, Nisena Gini (Tetranychus cinnabarinus), Kanzano, Mite (Tetranychus kanzawai ishida), namino mite (Tetranychus urticae Koch), chia nonagasabidaji (Acaphylla theae), mandarin orange (Aculops pelekassi), chianosabida two (Calacarus carinatus), pest On the other hand, it is strong! / And has an insecticidal effect.

 [0067] The substituted pyridinecarboxylic acid anilide derivative or a salt thereof represented by the general formula (I) of the present invention is preferably used as an agricultural or horticultural insecticide or an acaricide. It exhibits excellent control effects against various pests such as insect pests and sanitary pests, and can be used as a pest control agent in a wide range of fields. Examples of these pests include, for example, Rufidens Bigot, etc., Musca domestica uicina MACQUART, etc., Housefly, Gasterophilus intestinalis, etc. spirocularis, etc., Culex pipiens pallens, Shimano, madara force (An opheles sinensis) ^ Aedes japonicus, etc nocephalides felis), Meno: iACtenocepnaiides canis), Anthropaceae such as Pmex irritans, Ticks such as Ixodes ovatus Neumann, Scorpionaceae such as Euproctis similes, Sitophilus zo Vespa, Vespa simillima xanthoptera Cameron, etc. pubis), white-tailed termites (Reticulitermes speratus), termites (Copt otermes formosanus), etc .; Can be mentioned.

[0068] Agricultural and horticultural agents, in particular, agricultural and horticultural insecticides or acaricides, containing a substituted pyridinecarboxylic acid anilide derivative represented by the general formula (I) of the present invention or a salt thereof as an active ingredient are paddy field crops. It has a remarkable control effect against the above-mentioned pests that damage field crops, fruit trees, vegetables, other crops and flowers, etc., so that the occurrence of pests may occur before or after the occurrence of pests. When confirmed, it is treated with paddy fields, fields, fruit trees, vegetables, other crops, flower seeds, paddy water, foliage, or soil to provide the agricultural and horticultural insecticide of the present invention. The effect of the period is produced.

 The plant that can use the agricultural and horticultural agent of the present invention is not particularly limited, and examples thereof include the following plants.

 [0069] Kinds (for example, rice (Oryza sativa), barley (Hordeum vulgare), wheat (Triticum aestivum), rye (Secale cereale), oats (Avena), corn (Zea mays), high salmon, etc., Beans (soybeans, red beans, broad beans, peas, peanuts, etc.), fruit trees (fruits, apples, citrus fruits, pears, grapes, peaches, plums, cherry peaches, tarmi, almonds, bananas, strawberries, etc.), vegetables (cabbage, Tomato, spinach, broccoli, lettuce, onion, leek, bell pepper, etc.), root vegetables (carrot, potato, sweet potato, radish, lotus root, turnip, etc.), processing crops (cotton, hemp (Linum usita tissimum), koso (Broussonetia kasinoki Nomata (Edgeworthia papyrifera), 禾 禾 重 (Brassica napus), heat (Beta vulgaris) hops, sugar cane (Saccharum officinaru m), sugar beet (Beta vulgaris var. Saccharifera), ory: 7, rubber, coffee Tanoku , Tea, etc.), potatoes (cabochia, cucumber, watermelon, melon, etc.), pastures (orchard grass, sorghum, timosi, clover, alfalfa, etc.), turf (Korea turf, bentgrass, etc.), crops for flavoring It can be used for plants such as lavender (Lavandula officinalis CHAIX), rosemary, thyme, parsley, pepper, ginger, etc., and flowers (chrysanthemum, rose, orchid, etc.).

 [0070] In addition, in recent years, genetically modified crops (herbicide-resistant crops, pest-resistant crops incorporating insecticidal protein production genes, disease-resistant crops incorporating resistance-inducing substance production genes against diseases, crops with improved taste, and preservation stability have been improved. Crops, yield-enhancing crops, etc.), insect pheromones (such as turkeys, snails, and moths), IPM (Integrated Pest Management) technology using natural enemy insects, etc. The agrochemical composition can be used in combination with these techniques or systematized.

 [0071] The agricultural and horticultural chemicals of the present invention are generally used in a form convenient for use according to a conventional method for agricultural chemical formulations.

That is, the substituted pyridinecarboxylic acid anilide derivative represented by the general formula (I) or a salt thereof is dissolved in an appropriate inert carrier or, if necessary, together with an auxiliary agent in an appropriate ratio. Separated, suspended, mixed, impregnated, adsorbed or adhered, and formulated into appropriate dosage forms such as suspensions, emulsions, solutions, wettable powders, wettable granules, granules, powders, tablets, packs, etc. And use it.

 [0072] The inert carrier that can be used in the present invention may be either solid or liquid. Examples of the material that can be a solid carrier include soybean flour, cereal flour, wood flour, bark flour, and sawdust. , Tabacco stem powder, walnut shell powder, bran, fiber powder, residues after extraction of plant extracts, synthetic polymers such as ground synthetic resin, clays (eg kaolin, bentonite, acid clay), talc (eg Talc, pyrophyllite, etc.), silica {eg, diatomaceous earth, silica sand, mica, white carbon (some synthetic highly dispersed silicic acid, also called hydrous fine silicon, hydrous silicic acid, and some products contain calcium silicate as the main component.)} , Activated charcoal, iow powder, pumice, calcined diatomaceous earth, brick ground, fly ash, sand, calcium carbonate, calcium phosphate and other inorganic mineral powders, polyethylene, polypropylene, Plastic carriers vinylidene chloride, ammonium sulfate, ammonium phosphate, ammonium nitrate, can be mentioned urea, fertilizer salts depreciation etc., compost and the like, which are used alone or in the form of a mixture of two or more.

 [0073] The material that can be used as a liquid carrier is selected from those having solvent ability itself, and those that can disperse the active ingredient compound with the aid of an auxiliary agent without having solvent ability. The following carriers can be exemplified as typical examples, but these are used alone or in the form of a mixture of two or more thereof, for example, water, alcohols (for example, methanol, ethanol, isopropanol, butanol, ethylene glycol, etc.), ketones (Eg, acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, etc.), ethers (eg, ethyl ether, dioxane, cellosolve, dipropyl ether, tetrahydrofuran, etc.), aliphatic hydrocarbons (Eg kerosene, mineral oil), aromatic hydrocarbons (eg benzene) , Toluene, xylene, solvent naphtha, alkyl naphthalenes, etc.), halogenated hydrocarbons (eg dichloroethane, chloroform, carbon tetrachloride, chlorinated benzene, etc.), esters (eg ethyl acetate, diisopropylpropyl phthalate, di) Butyl phthalate, dioctyl phthalate, etc.), amides (eg, dimethylformamide, jetylformamide, dimethylacetamide, etc.), nitriles (eg, acetonitrile, etc.), dimethyl sulfoxides, and the like.

[0074] As other adjuvants, typical adjuvants exemplified below can be mentioned, and these adjuvants are used depending on the purpose, and singly, in some cases, two or more kinds of adjuvants are used. Used together or In some cases it is possible to use no adjuvants at all.

 Surfactants are used for the purpose of emulsifying, dispersing, solubilizing and / or wetting the active ingredient compounds, such as polyoxyethylene alkyl ethers, polyoxyethylene alkyl ethers, polyoxyethylene higher fatty acid esters, polyoxyethylenes. Examples of surfactants such as lenic resin acid ester, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, alkyl aryl sulfonate, naphthalene sulfonic acid condensate, lignin sulfonate, and higher alcohol sulfate Show power S

 Further, for the purpose of stabilizing the dispersion of the active ingredient compound, sticking and / or binding, the following auxiliary agents can be used, such as casein, gelatin, starch, methylcellulose, carboxymethylcellulose, gum arabic, Adjuvants such as polybulal alcohol, pine oil, coconut oil, bentonite and lignin sulfonate can also be used.

[0075] In order to improve the fluidity of solid products, the following adjuvants may be used, and for example, adjuvants such as waxes, stearates and alkyl phosphates may be used. As a peptizer for a suspension product, for example, an auxiliary such as naphthalenesulfonic acid condensate or condensed phosphate is used.

 As the antifoaming agent, for example, an auxiliary agent such as silicone oil can be used. As preservatives, 1,2-benzisothiazoline-1-3-one, parachlorometaxylenenole, butyl noroxybenzoate and the like can also be added.

 Furthermore, functional spreading agents, activity enhancers such as metabolic degradation inhibitors such as piperonyl butoxide, antifreezing agents such as propylene glycol, antioxidants such as BHT, ultraviolet absorbers, etc., as necessary Additives can also be added.

[0076] The blending ratio of the active ingredient compound can be adjusted as necessary, and it can be used by appropriately selecting from the range of 0.0;! To 90 parts by weight in 100 parts by weight of the agricultural and horticultural insecticide. For example, in the case of a powder or granule, 0.0;! To 50% by weight, and in the case of an emulsion or wettable powder, 0.0;! To 50% by weight is appropriate.

The agricultural and horticultural chemicals of the present invention are predicted to generate pests in an effective amount for controlling pests as they are, or appropriately diluted with water or suspended to control various pests. It may be used by applying it to crops that are unfavorable or where generation is not desirable.

 The amount of the agricultural and horticultural agent used in the present invention depends on various factors such as purpose, target pests, crop growth status, pest occurrence tendency, weather, environmental conditions, dosage form, application method, application location, application time, etc. Although it varies, the active ingredient compound may be appropriately selected according to the purpose from the range of 10 OOlg to 10 kg, preferably 0.01 g to 1 kg per 10 are.

[0077] The agricultural and horticultural agents of the present invention are further used for other agricultural and horticultural insecticides, acaricides, and nematicides for the purpose of expanding pests to be controlled, the appropriate control period, or reducing the dosage. It can be used in combination with herbicides, fungicides, biological pesticides, etc., and can be used in combination with herbicides, plant growth regulators, fertilizers, etc., depending on the situation of use.

 Other agricultural and horticultural insecticides, acaricides, and nematicides used for this purpose include, for example, ethion, trichlorfone, methamidophos, acephete, dichlorvos, mevinphos, monocrotofos, malati, dimethoate, formimotin, mecarbam , Nomidothion, thiomethone, disulfoton, oxydeprophos, nared, methyl parathion, fenitrothion, sianophos, propaphos, fenthion, prothiophos, profenophos, isofenphos, temefos, phentoate, dimethylvinphos, chlorfevinphos, tetrachlorvinphos, oxime, oxime, Genius, pyracrofos, methidathion, black mouth pyrifos, chlorpyrifos' methinore, pyridafenthion, diazinon, pirimiphosmethinore, hosalon, phosmeth , Di-O Kisabenzohosu, Kinanorehosu, Tenorebuhosu, ethoprophos, cadusafos, female Norre Fen host, DPS (NK- 0795),

[0078] Phosphocanoleb, phenamiphos, isoamidophos, phosthiazete, isazofos, enaprophos, fenthion, phoschetan, diclofenthion, thionazine, sulprophos, phensulfothion, diamidafos, pyrethrin, allethrin, praretrin, resmethrin, permethrin, tefluthrin Permethrin, alpha cypermethrin, cyhalothrin, lambda cihalothrin, denoretamethrin, acrinatrine, fenvalerate, esfenvalerate, cycloprotorin, etofenprox, no, norefenprox, silaflufen, flucitrinate, fulvalinate, mesomil, Oxamil, Choji Kanoleb, Aldikarp, Aranikarp, Cartap Metolcarb, Kishirikarubu, Provo sake, Fuenokishikarupu, Fuenobukarupu, E Chio Fen Culp, Fuenochiokarupu, Bifenazate, BPMC, Force Noreno Linole, Pirimicurve, Carbofuran, Carbosulfurfan, Fraciocarp, Benfuracarp, Aldoxycarp, Difenthiuron, Diflubenzuron, Tefnorebenzuron, Hexafnoremron, Nonofeneron, Fulerofrone Chlorfluzuron, fenbutasine oxide, tricyclohexyltin hydroxide, sodium oleate, potassium oleate, methoprene, hydraprene, vinapacryl, amitraz, dicohonole, kenorecene, chronolevendilate, phenisobromolate, tetradiphone , Bensultap, benzomate, tebufenozide, methoxyphenozide, pyridalinole,

[0079] Chromafenozide, propargite, acequinosyl, endosulfan, diofenolan, chlorfenapyr, fenpyroximate, tolfenvirad, fipronil, tebufenvir, triazamate, etoxazole, hexithiazotus, nicotine sulfate, ditenbilam, thiapridum, thiapridum, thiapridum , Dinotephran, funoreinazinum, pyriproxyfen, hydramethenolenone, pyrimidifen, pyridaben, profedin, thiocyclam, fenazaquin, quinomethionate, indoxacarp, polynactin complex, milbemectin, abamethatin, emamectin 'benzoate, spinosad, BT (Bacillus thuringiensis), Azadeiractin, Roteno And horticultural insecticides, acaricides, nematicides such as methacrylic acid, hydroxypropyl starch, levamisole hydrochloride, metam 'sodium, morantel tartrate, dazomet, triclamide, bastoria, monacrosporum' Can

[0080] Agricultural and horticultural fungicides used for the same purpose include, for example, sulfur, lime sulfur mixture, basic copper sulfate, iprobenfos, edifenfos, torque port phos'methyl, tyram, polycarnomate, dinebu, Manzeb, mancozeb, propineb, thiophanate, thiophanate methyl, benomyl, iminotazine acetate, iminotazine albosylate, mepronil, phenolate, pencyclon, furamethopyl, tifluzamide, metalaxyl, oxadixil, carpropamide, diclofluanide, fursulfamide , Chlorothalonyl, Cresoxime 'Methinole, Phenoxanil, Himexazole, Etalomezonole, Funoleonoleimide, Procymidone, Vinclozoline, Iprodione, Triadimephone, Vitertanol, Trifanolemi Nore, Ipukona Zonore, Funorekonazo one Norre, professional pico Nazo Norre. Di Hue saw Nazo Norre, Mikurobutaninore, Tet Laconazonole, Hexaconazonore, Tebuconazonore, Thiazininore, Imibenconazonore, Prochloraz, Pefrazoate, Ciproconazonore, Isoprothiolane, Phenalimonole, Pyrimethanil, Mepanipyroxime, Pyrifenazox, Fluazinam Clostidin Agricultural and horticultural fungicides such as propenazole, benzobenzofural S-methyl, fusalide, tricyclazole, pyroxylone, quinomethionate, oxolic acid, dithianone, kasugamycin, validamycin, polyoxin, blasticidin, streptomycin, etc. ,

 [0081] Similarly, herbicides include, for example, darifosate, sulphosate, dalfosinate, bialaphos, butamifos, esprocarp, prosulfocarp, beven curve, pyributycarp, ashram, linuron, diemron, isouron, bensulfuron methyl, cyclosulfamuron, sinosnorephrone, pyra Zosnolevonechinore, Azimusnoreflon, Imazosnorefuron, Teninoreclonore, Araclonore, Pretiraclonore, Chlomeprop, Etobenzanide, Mefenaset, Pendimethalin, Bifenox, Acifluophene, Lactofene, Cihalo Hop Butyl , Ioxul, Bromobutide, Aloxidim, Cetoxidim, Napropamide, Indanophane, Pyrazolate, Benzophenap, Pilaf Fenethyl, imazapyr, snolefentrazone, caffeenstromole, bentoxazone, oxadiazone, noraquat, diquat, pyriminobac, simazine, atrazine, dimetamethrin, triadifram, benfrecetate, fluthiaset methyl, quizalofop'ethyl, bentazone, calcium peroxide, etc. Can be exemplified.

[0082] In addition, as biological pesticides, for example, nuclear polyhedrosis virus (NPV), granulosis virus (GV), cytoplasmic polyhedrosis virus (CPV), insect box virus (CPV) Entomopox virus, EPV), such as virus SeiHitoshi ¹ J, monochrome sports Riu arm 'Fimatono gum (Monacrosporium phymatophagum), Steiner Nema' Kapokapusae (Steinemema carpocapsae), Sutainanema 'Kushide (Stein ernema kushidai), Pasutsuria. Bae Netoransu (Pasteuria penetrans ) Microbial pesticides used as insecticides or nematicides such as Trichoderma lignorum, Agrobacterium radiobactor, non-pathogenic Enore Vinia 'Erwinia carotovora ), Nochinoles' Bacillus subtilis, etc. Similar effects can be expected when used in combination with a microbial pesticide used as a fungicide, a biopesticide used as a herbicide such as Xanthomonas campestris.

[0083] In addition, as biopesticides, for example, Encarsia formosa, Aphidius colemani, Aphidoletes aphidimyza, Diglyphus isaea, Dacly, and ibimos ), Chijikafu, Lida: = · (Ph ytoseiulus persimilis, Ymbridseius cucumeris), natural enemies such as Orius sauteri, Beauveria brongniart ii (Z) —10-tetradecenyl acetate, (Z) —8-dodecenyl acetate, (Z) —8-dodecenyl acetate, (Z) —11-tetradecenyl acetate, (Z) — It can also be used in combination with pheromone agents such as 13 icosene 10-on, 14-methyl-1-octadecene.

 Example

 Hereinafter, the substituted pyridinecarboxylic acid anilide derivative represented by the general formula (I) of the present invention will be described with reference to examples, but the present invention is not limited thereto. Example 1. N— {3-Isobutyl-4 [l-methoxy-2, 2, 2-trifluoro-1- (trifluoromethyl) ethyl] phenyl} 2 methylpyridine-3 force rubonic acid amide (Compound No. 1-25) )Manufacturing of

 2 Methyl-3 pyridinecarboxylic acid (136 mg, 1 mmol), 3 Isobutyl-4 [1-methoxy 2, 2, 2 trifluoro-1 (trifluoromethinole) ethinole] aniline (329 mg, 1 mmol), 2-chloro-1 methyl Pyridinium muzide (255 mg, 1 mmol) and tritinoreamine (303 mg, 3 mmol) were dissolved in tetrahydrofuran (10 mU and heated to reflux for 3 hours. The reaction solution was diluted with ethyl acetate and washed with water. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane: ethyl acetate = 1: 2) to obtain the desired product (lOOmg). Yield obtained as crystals: 22%

Physical property: Melting point 174-175 ° C [0085] Example 2 Ν Propionyl Ν— {3 Isobutyl-4 [1-methoxy-2,2,2-trifluoro-1 (trifluoromethyl) ethyl] phenyl} 2 methylpyridine-3-carboxylic acid amide (compound Production of No. 1—42)

 Sodium hydride (purity 62% oil disperse product, 16 mg, 0.4 mmol) was stirred with N- {3-isobutyl-4 [1-methoxy-2, at room temperature while stirring in anhydrous tetrahydrofuran (3 mU). 2,2-trifluoro-1 (trifluoromethinole) ethinore] phenyl} A solution of 2-methylpyridine 3-strong rubonic acid amide in anhydrous tetrahydrofuran (3 mL) was added dropwise after 30 minutes of stirring at 30 ° C. Under the same temperature, an anhydrous tetrahydrofuran (0.5 mU solution) of propioyl olide (0.034 g, 0.36 mmol) was added dropwise at 30 ° C. for 15 minutes, followed by stirring at 50 ° C. for 45 minutes. Then, water (30 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate, washed with water and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure, and the resulting residue was subjected to silica gel column chromatography (hexane: acetic acid). At Jetil = 1: 2) It was obtained pasty desired product of (116 mg) by pollock Rukoto.

 Yield: 62%

 Physical property: Refractive index 1 · 4990 (23. 6 ° C)

Example 3 · N Isopropoxymethyl-N— {3 Isobutyl-4 [1-Methoxy-2,2,2-trifluoro-1 (trifluoromethinole) ethinole] phenyl} 2-methylpyridine —3 Carboxyl Production of acid amide (Compound No. 1-40)

Sodium hydride (purity 62% oil disperse product, 16 mg, 0.4 mmol) was stirred with N- {3-isobutyl-4 [1-methoxy-2, at room temperature while stirring in anhydrous tetrahydrofuran (3 mU). 2,2-trifluoro-1 (trifluoromethinole) ethinole] phenyl} A solution of 2-methylpyridine 1- 3 carboxylic acid amide (0.15 g, 0.33 mmol) in anhydrous tetrahydrofuran (3 mL) was added dropwise. After stirring for 30 minutes at 30 ° C, anhydrous tetrahydrofuran (0.5mU solution of chloromethyl isopropyl ether (0.5g, 0.54mmol), then dimethylformamide (0.3mL) was added dropwise at the same temperature. The reaction was stirred for 30 minutes at 30 ° C and then for 2 hours at 50 ° C. After cooling, water (30 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate, washed with water, dried over anhydrous sodium sulfate, and then under reduced pressure. The solvent was distilled off to give a residue. Mosquito gel column chromatography (hexane: acetic acid Echiru = 1: 2) Bae purified by a A single target product (155 mg) was obtained.

 Yield: 89%

 Physical property: Refractive index 1 · 4931 (23. 3 ° C)

 The following are typical preparation examples and test examples of the present invention, but the present invention is not limited thereto.

 In the preparation examples, “parts” means “parts by weight”.

 Formulation Example 1

 Compounds listed in Table 1 10 parts

 70 copies

 N-10 parts

 With polyoxyethylene nouryl phenyl ether

 Mixture with calcium alkylbenzenesulfonate 10 parts

 The above is mixed and dissolved uniformly to obtain an emulsion.

[0088] Formulation Example 2

 Compounds listed in Table 1 3 parts

 82 parts of clay powder

 Diatomaceous earth powder 15 parts

 The above is uniformly mixed and pulverized to obtain a powder.

[0089] Formulation Example 3

 Compounds listed in Table 1 5 parts

 90 parts of mixed powder of bentonite and clay

 Calcium lignin sulfonate 5 parts

 The above is uniformly mixed, kneaded with an appropriate amount of water, granulated and dried to give granules [0090] Formulation Example 4

 Compounds listed in Table 1 20 parts

 Kaolin and synthetic highly dispersed silicic acid 75 parts

 Ciethylene Nonino Lefuenino Leitenore and

'Mixture 5 parts The above is uniformly mixed and ground to obtain a wettable powder.

[0091] Test Example 1 Acaricidal test against Tetranychus urticae

 A 2 cm diameter kidney leaf leaf disk was placed on wet filter paper. After inoculating 10 adult female nymph mite, 50 ml of a drug solution diluted with 500 ppm and 50 ppm of a preparation containing the compound shown in Table 1 as an active ingredient was sprayed. Survival was investigated 2 days after treatment. The corrected death rate was calculated according to the following formula and judged according to the following criteria. 2 continuous operation at 25 ° C.

[0092] [Equation 1] Surviving number of untreated plots Surviving number of treated plots

 Corrected death rate (%) = X

 Number of untreated areas

[0093] Judgment criteria: Α ··· Corrected death rate 100%

 補正 ... Adjusted death rate 99% ~ 90%

 Adjusted death rate 89% -80%

 D .. · Adjusted death rate 79% ~ 50%

[0094] As the comparative compound, compounds Nos. 3-3 to 5 described in JP-A-2003-48878 were used.

[0095] [Chemical 6]

 As a result of the above test, the compounds of the present invention No. 1-8—1-11, 1 22, 1 25, 1 28, 1-30—33, 1—35, 1-37—59, 1-61—78, The compounds 1-80, 1-82, 1-89 and 1-90 showed A activity at both 500 ppm and 50 ppm concentrations. On the other hand, all three control compounds showed no acaricidal activity even at a concentration of 500 ppm.

This application is based on Japanese Patent Application No. 2006-276895 filed in Japan. All of which are incorporated herein.

Claims

Claim [1] General formula (I)

 [Chemical 1]

{Where R ¹ is

 : ia) hydrogen atom,

 : 2a) C-C alkyl group,

 1 6

 : 3a) a halo C-C alkyl group,

 1 6

 : 4a) C 1 -C alkylcarbonyl C 1 -C alkyl group,

 1 6 1 6

 : 5a) C 1 -C cycloalkyl group,

 3 6

 : 6a) Halo C-C cycloanolenoquinole group,

 3 6

 '7a) C-C cycloalkyl C-C alkyl group,

 3 6 1 6

 '8a) a halo C-C cycloalkyl C-C alkyl group,

 3 6 1 6

'9a) C 1 -C alkenyl group,

 2 6

 10a) a halo C-C canolekenino group,

 2 6

 11a) C 1 -C alkynyl group,

 2 6

 12a) a halo C 1 -C alkynyl group,

 2 6

 13a) C-C alkoxy C-C alkyl group.

 1 6 1 6

 14a) a halo C-C alkoxy C-C alkyl group,

 1 6 1 6

 15a) C 1 -C alkoxy C 1 -C alkoxy C 1 -C alkyl group

1 6 1 6 1 6

 16a) C 1 -C alkylthio C 1 -C alkyl group.

 1 6 1 6

 17a) Halo C 1 -C alkylthio C 1 -C alkyl group,

 1 6 1 6

 18a) C 1 -C alkyl sulfier C 1 -C alkyl group,

1 6 1 6

19a) Halo C 1 -C alkyl sulfiel C 1 -C anorequinole group,

 1 6 1 6

 20a) C 1 -C alkylsulfonyl C 1 -C alkyl group,

1 6 1 6

21a) a halo C-C alkylsulfonyl C-C alkyl group, (22a) mono C-C alkylamino C-C alkyl group,

 1 6 1 6

 (23a) di C 1 -C alkylamino C 1 -C alkyl group which may be the same or different,

 1 6 1 6

 (24a) phenyl C 1 -C alkoxy C 1 -C alkyl group,

 1 6 1 6

 (25a) C 1 -C alkylcarbonyl group,

 1 6

 (26a) a halo C -C alkylcarbonyl group,

 1 6

 (27a) C 1 -C alkoxy C 1 -C alkylcarbonyl group,

 1 6 1 6

 (28a) C 1 -C alkoxycarbonyl group,

 1 6

 (29a) C-C alkoxy C-C alkoxycarbonyl group,

 1 6 1 6

 (30a) a halo C -C alkoxycarbonyl group,

 1 6

 (31a) C 1 -C alkylthiocarbonyl group,

 1 6

 (32a) mono C-C alkylaminocarbonyl group,

 1 6

 (33a) a di-C 1 -C alkylaminocarbonyl group which may be the same or different,

 1 6

 (34a) C-C alkoxycarbonyl C-C alkyl group,

 1 6 1 6

 (35a) C 1 -C alkylsulfonyl group,

 1 6

 (36a) a halo C -C alkylsulfonyl group,

 1 6

 (37a) Cyan C 1 -C alkyl group,

 1 6

 (38a) phenyl C 1 -C alkyl group,

 1 6

 (39a) Same or different

 (a) halogen atom, (b) cyano group, (c) nitro group, (d) C 1 -C alkyl group, (e) halo C 2 -Ca

 1 6 1 6 alkyl group, (f) C-C alkoxy group, (g) halo C-C alkoxy group, (h) C-C alkyl group

 1 6 1 6 1 6o group, (i) halo C-C alkylthio group, (j) C-C alkyl sulfier group, (k) halo C-C

 1 6 1 6 1 Alkylsulfier group, (1) C 1 -C alkylsulfonyl group, (m) Halo C 1 -C alkyls

6 1 6 1 6 sulfonyl group, (n) mono-C-Canololequinolamino group, (0) di-C-C-a which may be the same or different

 1 6 1 6 alkylamino group and (p) C 1 -C alkoxycarbonyl group

 1 6

A substituted phenyl c-c alkyl group having one or more substituents on the ring selected from

 1 6

 (40a) a phenoxycarbonyl group,

(41a) Same or different

(a) halogen atom, (b) cyano group, (c) nitro group, (d) C 1 -C alkyl group, (e) halo C 2 -Ca Alkyl group, (f) C-C alkoxy group, (g) halo C-C alkoxy group, (h) C-C alkyl group

1 6 1 6 1 6o group, (i) Halo C-C alkylthio group, (j) C-C alkylsulfinyl group, (k) Halo C-C

 1 6 1 6 1 Alkylsulfier group, (1) C 1 -C alkylsulfonyl group, (m) Halo C 1 -C alkyls

6 1 6 1 6 sulfonyl group, (n) mono-C-Canolenoquinamino group, (0) di-C-C-a may be the same or different

 1 6 1 6 alkylamino group and (p) c -c alkoxycarbonyl group

 1 6

A substituted phenoxycarbonyl group having one or more substituents selected on the ring,

(42a) phenylsulfonyl group,

(43a) Same or different

 (a) halogen atom, (b) cyano group, (c) nitro group, (d) C 1 -C alkyl group, (e) halo C 2 -Ca

 1 6 1 6 alkyl group, (f) C-C alkoxy group, (g) halo C-C alkoxy group, (h) C-C alkyl group

 1 6 1 6 1 6o group, (i) Halo C-C alkylthio group, (j) C-C alkylsulfinyl group, (k) Halo C-C

 1 6 1 6 1 Alkylsulfier group, (1) C 1 -C alkylsulfonyl group, (m) Halo C 1 -C alkyls

6 1 6 1 6 sulfonyl group, (n) mono-C-Canolenoquinamino group, (0) di-C-C-a may be the same or different

 1 6 1 6 alkylamino group and (p) c -c alkoxycarbonyl group

 1 6

A substituted phenylsulfonyl group having one or more substituents selected on the ring,

(44a) a di-C 6 -C anorequinolephosphono group which may be the same or different,

 1 6

 (45a) a di-C 6 -C anorequinolephosphonothio group which may be the same or different,

 1 6

 (46a) N-C-C alkyl-N-C-C alkoxycarbonylaminothio group,

 1 6 1 6

 (47a) N-C 1 -C alkyl- N-C _C alkoxycarbonyl C _C alkylaminothio group

 1 6 1 6 1 6

(48a) a di-C 6 -C alkylaminothio group which may be the same or different,

 1 6

 (49a) C 1 -C cycloalkylcarbonyl group,

 3 6

 (50a) C 1 -C alkyl C 1 -C cycloalkylcarbonyl group,

 1 6 3 6

 (51a) phenyl C 1 -C cycloalkylcarbonyl group,

 3 6

 (52a) Same or different

 (a) halogen atom, (b) cyano group, (c) nitro group, (d) C 1 -C alkyl group, (e) halo C 2 -Ca

 1 6 1 6 alkyl group, (f) C-C alkoxy group, (g) halo C-C alkoxy group, (h) C-C alkyl group

1 6 1 6 1 6o group, (i) Halo C-C alkylthio group, (j) C-C alkylsulfinyl group, (k) Halo C-C Alkylsulfiel group, (1) C 1 -C alkylsulfonyl group, (m) halo C 1 -C alkyls

6 1 6 1 6 sulfonyl group, (n) mono-C-Canolenoquinamino group, (0) di-C-C-a may be the same or different

 1 6 1 6 alkylamino group and (p) c -c alkoxycarbonyl group

 1 6

A substituted phenyl c-c cycloalkyl having one or more substituents on the phenyl ring selected from

 3 6 Norequinolecanoleboninole group,

 (53a) C 1 -C alkenyloxycarbonyl group,

 2 6

 (54a) phenyl C 1 -C alkoxycarbonyl group,

 1 6

 (55a) Same or different

 (a) halogen atom, (b) cyano group, (c) nitro group, (d) C 1 -C alkyl group, (e) halo C 2 -Ca

 1 6 1 6 alkyl group, (f) C-C alkoxy group, (g) halo C-C alkoxy group, (h) C-C alkyl group

 1 6 1 6 1 6o group, (i) Halo C-C alkylthio group, (j) C-C alkylsulfinyl group, (k) Halo C-C

 1 6 1 6 1 Alkylsulfier group, (1) C 1 -C alkylsulfonyl group, (m) Halo C 1 -C alkyls

6 1 6 1 6 sulfonyl group, (n) mono-C-Canolenoquinamino group, (0) di-C-C-a may be the same or different

 1 6 1 6 alkylamino group and (p) c -c alkoxycarbonyl group

 1 6

Substituted phenyl c-c alkoxycarbo having one or more substituents on the ring selected from

 1 6

Nyl group,

 (56a) a phenyl C 1 -C alkylcarbonyl group, or

 1 6

 (57a) Same or different

 (a) halogen atom, (b) cyano group, (c) nitro group, (d) C 1 -C alkyl group, (e) halo C 2 -Ca

 1 6 1 6 alkyl group, (f) C-C alkoxy group, (g) halo C-C alkoxy group, (h) C-C alkyl group

 1 6 1 6 1 6o group, (i) Halo C-C alkylthio group, (j) C-C alkylsulfinyl group, (k) Halo C-C

 1 6 1 6 1 Alkylsulfier group, (1) C 1 -C alkylsulfonyl group, (m) Halo C 1 -C alkyls

6 1 6 1 6 sulfonyl group, (n) mono-C-Canolenoquinamino group, (0) di-C-C-a may be the same or different

 1 6 1 6 alkylamino group and (p) c -c alkoxycarbonyl group

 1 6

A substituted phenyl c-c alkylcarbohydrate having one or more substituents on the ring selected from

 1 6

Le group

Indicates.

R ² is (lb) hydrogen atom,

(2b) a halogen atom,

(3b) a C 1 -C alkyl group,

 1 6

 (4b) a halo C 1 -C alkyl group,

 1 6

 (5b) Cyan group,

 (6b) a hydroxy group,

 (7b) C 1 -C anorecoxy group,

 1 6

 (8b) Halo C 1 -C anorecoxy group,

 1 6

 (9b) C-C alkoxy C-C alkoxy group,

 1 6 1 3

 (10b) Halo C-C alkoxy C-C alkoxy group,

 1 6 1 3

 (lib) C 1 -C alkylthio C 1 -C alkoxy group,

 1 6 1 3

 (12b) a halo C -C alkylthio C -C alkoxy group,

 1 6 1 3

 (13b) C 1 -C alkyl sulfiel C 1 -C alkoxy group,

 1 6 1 3

 (14b) Halo C 1 -C alkylsulfier C 1 -C alkoxy group,

 1 6 1 3

 (15b) C 1 -C alkylsulfonyl C 1 -C alkoxy group,

 1 6 1 3

 (16b) a halo C -C alkylsulfonyl C -C alkoxy group,

 1 6 1 3

 (17b) mono C 1 -C alkylamino C 1 -C alkoxy group,

 1 6 1 3

 (18b) di C 1 -C alkylamino C 1 -C alkoxy groups which may be the same or different,

 1 6 1 3

 (19b) c -c alkylthio group,

 1 6

 (20b) a halo C -C alkylthio group,

 1 6

 (21b) C 1 -C alkylsulfinyl group,

 1 6

 (22b) a halo C 1 -C alkylsulfinyl group,

 1 6

 (23b) C 1 -C alkylsulfonyl group,

 1 6

 (24b) a halo C -C alkylsulfonyl group,

 1 6

 (25b) an amino group,

 (26b) mono-C-Canorequinoleamino group,

 1 6

 (27b) a di-C 1 -C alkylamino group which may be the same or different,

 1 6

(28b) a phenoxy group, (29b) Same or different

 (a) halogen atom, (b) cyano group, (c) nitro group, (d) C 1 -C alkyl group, (e) halo C 2 -Ca

 1 6 1 6 alkyl group, (f) C-C alkoxy group, (g) halo C-C alkoxy group, (h) C-C alkyl group

 1 6 1 6 1 6o group, (i) Halo C-C alkylthio group, (j) C-C alkylsulfinyl group, (k) Halo C-C

 1 6 1 6 1 Alkylsulfier group, (1) C 1 -C alkylsulfonyl group, (m) Halo C 1 -C alkyls

6 1 6 1 6 sulfonyl group, (n) mono-C-Canolenoquinamino group, (0) di-C-C-a may be the same or different

 1 6 1 6 alkylamino group and (p) c -c alkoxycarbonyl group

 1 6

A substituted phenoxy group having one or more substituents selected from

 (30b) a phenylthio group,

 (31b) Same or different

 (a) halogen atom, (b) cyano group, (c) nitro group, (d) C 1 -C alkyl group, (e) halo C 2 -Ca

 1 6 1 6 alkyl group, (f) C-C alkoxy group, (g) halo C-C alkoxy group, (h) C-C alkyl group

 1 6 1 6 1 6o group, (i) Halo C-C alkylthio group, (j) C-C alkylsulfinyl group, (k) Halo C-C

 1 6 1 6 1 Alkylsulfier group, (1) C 1 -C alkylsulfonyl group, (m) Halo C 1 -C alkyls

6 1 6 1 6 sulfonyl group, (n) mono-C-Canolenoquinamino group, (0) di-C-C-a may be the same or different

 1 6 1 6 alkylamino group and (p) c -c alkoxycarbonyl group

 1 6

A substituted phenylthio group having one or more substituents selected from

(32b) phenylsulfier group,

(33b) Same or different

 (a) halogen atom, (b) cyano group, (c) nitro group, (d) C 1 -C alkyl group, (e) halo C 2 -Ca

 1 6 1 6 alkyl group, (f) C-C alkoxy group, (g) halo C-C alkoxy group, (h) C-C alkyl group

 1 6 1 6 1 6o group, (i) Halo C-C alkylthio group, (j) C-C alkylsulfinyl group, (k) Halo C-C

 1 6 1 6 1 Alkylsulfier group, (1) C 1 -C alkylsulfonyl group, (m) Halo C 1 -C alkyls

6 1 6 1 6 sulfonyl group, (n) mono-C-Canolenoquinamino group, (0) di-C-C-a may be the same or different

 1 6 1 6 alkylamino group and (p) c -c alkoxycarbonyl group

 1 6

A substituted phenylsulfinyl group having one or more substituents selected on the ring,

(34b) a phenylsulfonyl group,

(35b) Same or different (a) halogen atom, (b) cyano group, (c) nitro group, (d) C 1 -C alkyl group, (e) halo C _Ca

 1 6 1 6 alkyl group, (f) C-C alkoxy group, (g) halo C-C alkoxy group, (h) C-C alkyl group

 1 6 1 6 1 6o group, (i) Halo C-C alkylthio group, (j) C-C alkylsulfinyl group, (k) Halo C-C

 1 6 1 6 1 Alkylsulfier group, (1) C 1 -C alkylsulfonyl group, (m) Halo C 1 -C alkyls

6 1 6 1 6 sulfonyl group, (n) mono-C-Canolenoquinamino group, (0) di-C-C-a may be the same or different

 1 6 1 6 alkylamino group and (p) c -c alkoxycarbonyl group

 1 6

A substituted phenylsulfonyl group having one or more substituents selected on the ring,

(36b) a phenyl C-C alkoxy group, or

 1 6

 (37b) Same or different

 (a) halogen atom, (b) cyano group, (c) nitro group, (d) C 1 -C alkyl group, (e) halo C 2 -Ca

 1 6 1 6 alkyl group, (f) C-C alkoxy group, (g) halo C-C alkoxy group, (h) C-C alkyl group

 1 6 1 6 1 6o group, (i) Halo C-C alkylthio group, (j) C-C alkylsulfinyl group, (k) Halo C-C

 1 6 1 6 1 Alkylsulfier group, (1) C 1 -C alkylsulfonyl group, (m) Halo C 1 -C alkyls

6 1 6 1 6 sulfonyl group, (n) mono-C-Canolenoquinamino group, (0) di-C-C-a may be the same or different

 1 6 1 6 alkylamino group and (p) c -c alkoxycarbonyl group

 1 6

A substituted phenyl c-c alkoxy group having one or more substituents selected from the group

 1 6

Indicates.

 G is

 (lc) C 1 -C alkyl group,

 1 10

 (2c) a halo C 1 -C alkyl group,

 1 10

 (3c) C 1 -C alkenyl group,

 3 10

 (4c) a halo C 1 -C alkenyl group,

 3 10

 (5c) C 1 -C alkynyl group,

 3 10

 (6c) Halo C 1 -C alkynyl group,

 3 10

 (7c) C 1 -C cycloalkyl group,

 3 10

 (8c) Same or different

 (a) a halogen atom, (b) a C 1 -C anorequinole group, and (c) a halo C 1 -C alkyl group

 1 6 1 6

A substituted c-c cycloalkyl group having one or more substituents selected from (9c) C 1 -C cycloalkenyl group,

 3 10

 (10c) Same or different

 (a) a halogen atom, (b) a C 1 -C anorequinole group, and (c) a halo C 1 -C alkyl group

 1 6 1 6

A substituted c-c cycloalkenyl group having one or more substituents selected from

 3 10

 (11c) C 1 -C cycloalkyl C 1 -C anorequinole group, or

 3 8 1 6

 (12c) Halo C-C cycloalkyl C-C alkyl group

 3 8 1 6

Indicates.

 Z represents an oxygen atom or a sulfur atom.

 n represents an integer of 0 to 3.

 X may be the same or different

(Id) a halogen atom,

(2d) Cyan group,

(3d) a nitro group,

 (4d) a C 1 -C alkyl group, or

 1 6

 (5d) Halo C 1 -C alkyl group

 1 6

Indicates.

 m represents an integer of 0-4.

 Y can be the same or different

(le) a halogen atom,

(2e) Cyan group,

(3e) a nitro group,

(4e) hydroxyl group,

(5e) a mercapto group,

(6e) an amino group,

(7e) carboxyl group,

(8e) a C 1 -C alkyl group,

 1 6

 (9e) a halo C 1 -C alkyl group,

 1 6

(10e) C 1 -C alkenyl group, (l ie) Halo C— Calkenyl group,

 2 6

 (12e) c-c alkynyl group,

 2 6

 (13e) a halo C-C alkynyl group,

 2 6

 (14e) Tri C 1 -C alkylsilyl C which may be the same or different

 1 6 2

(15e) phenyl C-C alkynyl group,

 2 6

 (16e) c -c Anolecoxy C -C Anolecoxy

 1 6 c -c anolenoquinole group,

 1 6 1 6

 (17e) Hyd, Roxy c-C Anolequinole ¾,

 1 6

 (18e) c-c alkyl carbonyl xy c-canoleno, group,

1 6 1 6

 (19e) a C-C cycloalkyl group,

 3 6

 (20e) Halo C-C Cycloa / Requinole ¾,

 3 6

 (21e) c -c cycloalkyl

 3 6 c -c alkyl group,

 1 6

 (22e) a halo C-C cycloalkyl c-c alkyl group,

 3 6 1 6

 (23e) c-canoloxy group,

 1 6

 (24e) a non-C 1 -C anorecoxy group,

 1 6

 (25e) C-C canoloxy

 1 6 C -c alkoxy group,

 L 6

 (26e) Halo C -C Anolekoxy

 1 6 c -c alkoxy group,

 1 6

 (27e) phenyl c-c al'oxy group,

 1 6

 (28e) c -c alkoxy

 1 6 C -c alkyl group,

 L 6

 (29e) a halo C -C alkoxy C -c alkyl group,

 1 6 1 6

 (30e) C-C alkylthio ^ -group,

 1 6

 (31e) a halo C—C alkyl group,

 1 6

 (32e) c-c alkylsulf ^ 7-ynyl group,

 1 6

 (33e) a halo C—C alkyl sulfier group,

 1 6

 (34e) C-C alkyl sulphonyl group,

 1 6

 (35e) Noro C— C canolequol sulphonyl group,

 1 6

 (36e) c -c alkylthio

 1 6 c -c alkyl group,

 1 6

 (37e) halo C—C alkyl z thio c -c alkyl group,

 1 6 1 6

(38e) c-c alkylsnorrequinyl c-c arnolequinole group, (39e) a halo C 1 -C alkylsulfinyl C 1 -C alkyl group,

 1 6 1 6

 (40e) C 1 -C alkylsulfonyl C 1 -C alkyl group,

 1 6 1 6

 (41e) a halo C -C alkylsulfonyl C -C alkyl group,

 1 6 1 6

 (42e) mono C 1 -C alkylamino group,

 1 6

 (43e) diC 1 -C alkylamino groups which may be the same or different,

 1 6

 (44e) phenylamino group,

 (45e) mono C-C alkylamino C-C alkyl group,

 1 6 1 6

 (46e) diC 1 -C alkylamino C 1 -C alkyl group which may be the same or different,

 1 6 1 6

 (47e) phenyl group,

 (48e) Same or different

 (a) halogen atom, (b) cyano group, (c) nitro group, (d) C 1 -C alkyl group, (e) halo C 2 -Ca

 1 6 1 6 alkyl group, (f) C-C alkoxy group, (g) halo C-C alkoxy group, (h) C-C alkyl group

 1 6 1 6 1 6o group, (i) Halo C-C alkylthio group, (j) C-C alkylsulfinyl group, (k) Halo C-C

 1 6 1 6 1 Alkylsulfier group, (1) C 1 -C alkylsulfonyl group, (m) Halo C 1 -C alkyls

6 1 6 1 6 sulfonyl group, (n) mono-C-Canolenoquinamino group, (0) di-C-C-a may be the same or different

 1 6 1 6 alkylamino group and (p) c -c alkoxycarbonyl group

 1 6

A substituted phenyl group having one or more substituents selected on the ring,

 (49e) a phenoxy group,

 (50e) Same or different

 (a) halogen atom, (b) cyano group, (c) nitro group, (d) C 1 -C alkyl group, (e) halo C 2 -Ca

 1 6 1 6 alkyl group, (f) C-C alkoxy group, (g) halo C-C alkoxy group, (h) C-C alkyl group

 1 6 1 6 1 6o group, (i) Halo C-C alkylthio group, (j) C-C alkylsulfinyl group, (k) Halo C-C

 1 6 1 6 1 Alkylsulfier group, (1) C 1 -C alkylsulfonyl group, (m) Halo C 1 -C alkyls

6 1 6 1 6 sulfonyl group, (n) mono-C-Canolenoquinamino group, (0) di-C-C-a may be the same or different

 1 6 1 6 alkylamino group and (p) c -c alkoxycarbonyl group

 1 6

A substituted phenoxy group having one or more substituents selected from

 (51e) a heterocyclic group, or

(52e) Same or different (a) halogen atom, (b) cyano group, (c) nitro group, (d) C 1 -C alkyl group, (e) halo C _Ca

 1 6 1 6 alkyl group, (f) C-C alkoxy group, (g) halo C-C alkoxy group, (h) C-C alkyl group

 1 6 1 6 1 6o group, (i) Halo C-C alkylthio group, (j) C-C alkylsulfinyl group, (k) Halo C-C

 1 6 1 6 1 Alkylsulfier group, (1) C 1 -C alkylsulfonyl group, (m) Halo C 1 -C alkyls

6 1 6 1 6 sulfonyl group, (n) mono-C-Canolenoquinamino group, (0) di-C-C-a may be the same or different

 1 6 1 6 alkylamino group and (p) c -c alkoxycarbonyl group

 1 6

 A substituted heterocyclic group having one or more substituents selected from

 Indicates. Or

 (53e) Two adjacent Y's on the pyridine ring can be joined together to form a condensed ring, which can be the same or different

 (a) halogen atom, (b) cyano group, (c) nitro group, (d) C 1 -C alkyl group, (e) halo C 2 -Ca

 1 6 1 6 alkyl group, (f) C-C alkoxy group, (g) halo C-C alkoxy group, (h) C-C alkyl group

 1 6 1 6 1 6o group, (i) Halo C-C alkylthio group, (j) C-C alkylsulfinyl group, (k) Halo C-C

 1 6 1 6 1 Alkylsulfier group, (1) C 1 -C alkylsulfonyl group, (m) Halo C 1 -C alkyls

6 1 6 1 6 sulfonyl group, (n) mono-C-Canolenoquinamino group, (0) di-C-C-a may be the same or different

 1 6 1 6 alkylamino group and (p) c -c alkoxycarbonyl group

 1 6

 One or more substituents selected on the ring can also be present on the ring. }

 A substituted pyridinecarboxylic acid anilide derivative represented by the formula:

 [2] is

 (la) a hydrogen atom,

 (2a) a C 1 -C alkyl group,

 1 6

 (13a) C-C alkoxy C-C alkyl group,

 1 6 1 6

 (25a) C 1 -C alkylcarbonyl group,

 1 6

 (27a) C 1 -C alkoxy C 1 -C alkylcarbonyl group,

 1 6 1 6

 (28a) C 1 -C alkoxycarbonyl group,

 1 6

 (37a) Cyan C 1 -C alkyl group,

 1 6

 (40a) a phenoxycarbonyl group,

(41a) Same or different (a) halogen atom, (b) cyano group, (c) nitro group, (d) C 1 -C alkyl group, (e) halo C _Ca

 1 6 1 6 alkyl group, (f) C-C alkoxy group, (g) halo C-C alkoxy group, (h) C-C alkyl group

 1 6 1 6 1 6o group, (i) Halo C-C alkylthio group, (j) C-C alkylsulfinyl group, (k) Halo C-C

 1 6 1 6 1 Alkylsulfier group, (1) C 1 -C alkylsulfonyl group, (m) Halo C 1 -C alkyls

6 1 6 1 6 sulfonyl group, (n) mono-C-Canolenoquinamino group, (0) di-C-C-a may be the same or different

 1 6 1 6 alkylamino group and (p) c -c alkoxycarbonyl group

 1 6

A substituted phenoxycarbonyl group having one or more substituents selected on the ring,

(49a) C 1 -C cycloalkylcarbonyl group,

 3 6

 (50a) C 1 -C alkyl C 1 -C cycloalkylcarbonyl group,

 1 6 3 6

 (51a) phenyl C 1 -C cycloalkylcarbonyl group,

 3 6

 (52a) Same or different

 (a) halogen atom, (b) cyano group, (c) nitro group, (d) C 1 -C alkyl group, (e) halo C 2 -Ca

 1 6 1 6 alkyl group, (f) C-C alkoxy group, (g) halo C-C alkoxy group, (h) C-C alkyl group

 1 6 1 6 1 6o group, (i) Halo C-C alkylthio group, (j) C-C alkylsulfinyl group, (k) Halo C-C

 1 6 1 6 1 Alkylsulfier group, (1) C 1 -C alkylsulfonyl group, (m) Halo C 1 -C alkyls

6 1 6 1 6 sulfonyl group, (n) mono-C-Canolenoquinamino group, (0) di-C-C-a may be the same or different

 1 6 1 6 alkylamino group and (p) c -c alkoxycarbonyl group

 1 6

A substituted phenyl c-c cycloalkyl having one or more substituents on the phenyl ring selected from

 3 6 Norequinolecanoleboninole group,

 (53a) C 1 -C alkenyloxycarbonyl group,

 2 6

 (54a) phenyl C 1 -C alkoxycarbonyl group,

 1 6

 (55a) Same or different

 (a) halogen atom, (b) cyano group, (c) nitro group, (d) C 1 -C alkyl group, (e) halo C 2 -Ca

 1 6 1 6 alkyl group, (f) C-C alkoxy group, (g) halo C-C alkoxy group, (h) C-C alkyl group

 1 6 1 6 1 6o group, (i) Halo C-C alkylthio group, (j) C-C alkylsulfinyl group, (k) Halo C-C

 1 6 1 6 1 Alkylsulfier group, (1) C 1 -C alkylsulfonyl group, (m) Halo C 1 -C alkyls

6 1 6 1 6 sulfonyl group, (n) mono-C-Canolenoquinamino group, (0) di-C-C-a may be the same or different

1 6 1 6 alkylamino group and (p) c -c alkoxycarbonyl group Substituted phenyl c-c alkoxycarbo having one or more substituents on the ring selected from

 1 6

 Nyl group,

 (56a) a phenyl C 1 -C alkylcarbonyl group, or

 1 6

 (57a) Same or different

 (a) halogen atom, (b) cyano group, (c) nitro group, (d) C 1 -C alkyl group, (e) halo C 2 -Ca

 1 6 1 6 alkyl group, (f) C-C alkoxy group, (g) halo C-C alkoxy group, (h) C-C alkyl group

 1 6 1 6 1 6o group, (i) Halo C-C alkylthio group, (j) C-C alkylsulfinyl group, (k) Halo C-C

 1 6 1 6 1 Alkylsulfier group, (1) C 1 -C alkylsulfonyl group, (m) Halo C 1 -C alkyls

6 1 6 1 6 sulfonyl group, (n) mono-C-Canolenoquinamino group, (0) di-C-C-a may be the same or different

 1 6 1 6 alkylamino group and (p) c -c alkoxycarbonyl group

 1 6

 A substituted phenyl c-c alkylcarbohydrate having one or more substituents on the ring selected from

 1 6

 Le group

 The substituted pyridinecarboxylic acid anilide derivative or a salt thereof according to claim 1, wherein

[3] R ² is

 (lb) hydrogen atom,

 (2b) a halogen atom, or

 (7b) C 1 -C alkoxy group

 1 6

 The substituted pyridinecarboxylic acid anilide derivative or a salt thereof according to claim 1 or 2, wherein

[4] The substituted pyridine according to any one of claims 1 to 3, wherein G is an (lc) C 1 -C alkyl group.

 1 10

 Zincarboxylic acid anilide derivatives or salts thereof.

 [5] The substituted pyridinecarboxylic acid anilide derivative and the salt thereof according to any one of claims 1 to 4, wherein n is 0.

6. The substituted pyridinecarboxylic acid anilide derivative and the salt thereof according to any one of claims 1 to 5, wherein Z is an oxygen atom.

[7] Agricultural and horticultural medicine comprising the substituted pyridinecarboxylic acid anilide derivative or salt thereof according to any one of claims 1 to 6 as an active ingredient.

[8] The agricultural and horticultural agent according to claim 7, which is an agricultural or horticultural insecticide or acaricide. [9] A method for using an agricultural and horticultural agent characterized by treating an effective amount of the agricultural and horticultural agent according to claim 7 or 8 to a target plant or soil in order to control pests from useful plants. .