JP5205274B2 - Novel pyrazole derivatives, pest control agents and methods of use thereof - Google Patents

Description

  The present invention relates to a novel pyrazole derivative, particularly an N-2- (substituted pyrazolyl) ethylcarboxamide derivative or a salt thereof, and a pest control agent containing the compound as an active ingredient, particularly a plant disease control agent or a nematicide and its Regarding usage.

Conventionally, it is known that certain N-2- (substituted pyrazolyl) ethylcarboxamide derivatives are useful as plant disease control agents (see, for example, Patent Document 1 or 2). However, its plant disease control effect is not sufficient, and it is not known that these compounds have nematicidal activity.
International Publication No. 2006/108791 Pamphlet International Publication No. 2006/108792 Pamphlet

  In crop production such as agriculture and horticulture, damage caused by diseases is still large, and new plant disease control with a low dose and wide control spectrum due to the occurrence of disease resistant to existing drugs and the burden on the global environment Development of agents is desired. In addition, various labor-saving application methods are required due to the aging of farmers, and the creation of plant disease control agents having characteristics suitable for these application methods. The present invention provides a novel N-2- (substituted pyrazolyl) ethylcarboxamide derivative useful as a plant disease control agent or nematicide in order to meet these demands.

As a result of intensive studies to solve the above problems, the present inventors have found that N-2- (substituted pyrazolyl) ethylcarboxamide derivatives represented by the general formula (I) of the present invention or salts thereof are used as plant disease control agents. In addition to showing an excellent control effect, the present inventors have found that it has an extremely wide bactericidal spectrum and nematicidal activity, and has completed the present invention. That is, the present invention
[1] General formula (I)

{Wherein R ¹ and R ² may be the same or different,
(1a) a hydrogen atom; or
(2a) represents a (C ₁ -C ₆ ) alkyl group. R ¹ and R ² are together
(3a) (C ₃ -C ₆ ) cycloalkane may be formed.

R ³ is
(1b) a hydrogen atom;
(2b) a (C ₁ -C ₆ ) alkyl group;
(3b) a (C ₁ -C ₆ ) alkoxy (C ₁ -C ₆ ) alkyl group;
(4b) a (C ₁ -C ₆ ) alkylcarbonyl group; or
(5b) represents a (C ₁ -C ₆ ) alkoxycarbonyl group.
Ar is
(1c) a phenyl group; or
(2c) (i) pyridyl group, (ii) pyrimidinyl group, (iii) pyrazinyl group, (iv) pyrazolyl group, (v) furyl group, (vi) thienyl group, (vii) oxazolyl group, (viii) isoxazolyl group , (Ix) a thiazolyl group, (x) an isothiazolyl group, and (xi) a heterocyclic group selected from a thiadiazolyl group.

X may be the same or different,
(1d) a halogen atom;
(2d) a cyano group;
(3d) a nitro group;
(4d) a (C ₁ -C ₆ ) alkyl group;
(5d) a halo (C ₁ -C ₆ ) alkyl group;
_{(6d) (C 3 -C 6} ) cycloalkyl group;
(7d) a (C ₁ -C ₆ ) alkoxy group;
(8d) a halo (C ₁ -C ₆ ) alkoxy group;
(9d) a (C ₁ -C ₆ ) alkylthio group;
(10d) a halo (C ₁ -C ₆ ) alkylthio group;
(11d) a (C ₁ -C ₆ ) alkoxy (C ₁ -C ₆ ) alkylthio group;
(12d) a (C ₁ -C ₆ ) alkylsulfinyl group;
(13d) a halo (C ₁ -C ₆ ) alkylsulfinyl group;
(14d) a (C ₁ -C ₆ ) alkylsulfonyl group;
(15d) a halo (C ₁ -C ₆ ) alkylsulfonyl group;
(16d) an amino group;
(17d) a mono (C ₁ -C ₆ ) alkylamino group;
(18d) di (C ₁ -C ₆ ) alkylamino groups which may be the same or different;
(19d) piperidino group;
(20d) may be the same or different, (i) a (C ₁ -C ₆ ) alkyl group, (ii) a halo (C ₁ -C ₆ ) alkyl group, (iii) a (C ₁ -C ₆ ) alkoxy group, And (iv) a substituted piperidino group having one or more substituents selected from halo (C ₁ -C ₆ ) alkoxy groups;
(21d) a phenyl group;
(22d) may be the same or different, and (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, ( v) a substituted phenyl group having one or more substituents selected from (C ₁ -C ₆ ) alkoxy groups, and (vi) halo (C ₁ -C ₆ ) alkoxy groups;
(23d) a phenoxy group;
(24d) may be the same or different, and (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, ( v) a (C ₁ -C ₆ ) alkoxy group, and (vi) a substituted phenoxy group having one or more substituents selected from a halo (C ₁ -C ₆ ) alkoxy group;
(25d) a phenyl (C ₁ -C ₆ ) alkyl group;
(26d) may be the same or different, and (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, ( v) a substituted phenyl (C ₁ -C ₆ ) alkyl having one or more substituents selected from a (C ₁ -C ₆ ) alkoxy group and (vi) a halo (C ₁ -C ₆ ) alkoxy group on the ring A group; and
(27d) shows a substituent selected from a (C ₁ -C ₆ ) alkoxyimino (C ₁ -C ₆ ) alkyl group,
n shows the integer of 0-5.
In addition, when n is an integer of 2 to 5, two adjacent Xs are combined
_{(28d) (C 3 -C 5} ) alkylene group;
_{(29d) (C 3 -C 5} ) alkenylene group;
_{(30d) (C 2 -C 4} ) alkyleneoxy group; or
(31d) A (C ₁ -C ₃ ) alkylenedioxy group optionally substituted by a halogen atom can be shown.

Y ¹ , Y ² and Y ³ may be the same or different,
(1e) a hydrogen atom;
(2e) a halogen atom;
(3e) a cyano group;
(4e) a (C ₁ -C ₆ ) alkyl group;
(5e) a halo (C ₁ -C ₆ ) alkyl group;
(6e) a (C ₁ -C ₆ ) alkylcarbonyl group;
(7e) a (C ₁ -C ₆ ) alkoxy group;
(8e) a halo (C ₁ -C ₆ ) alkoxy group;
(9e) a (C ₁ -C ₆ ) alkoxy (C ₁ -C ₆ ) alkyl group;
(10e) a (C ₁ -C ₆ ) alkylthio group;
(11e) a halo (C ₁ -C ₆ ) alkylthio group;
(12e) a (C ₁ -C ₆ ) alkylsulfinyl group;
(13e) a halo (C ₁ -C ₆ ) alkylsulfinyl group;
_{(14e) (C 1 -C 6} ) alkylsulfonyl group;
(15e) a halo (C ₁ -C ₆ ) alkylsulfonyl group;
(16e) an amino group;
(17e) a mono (C ₁ -C ₆ ) alkylamino group;
(18e) di (C ₁ -C ₆ ) alkylamino groups which may be the same or different;
(19e) amino-carbonyl group;
(20e) a mono (C ₁ -C ₆ ) alkylamino-carbonyl group;
(21e) di (C ₁ -C ₆ ) alkylamino-carbonyl groups which may be the same or different;

(22e) a phenyl group;
(23e) may be the same or different, (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, ( v) (C ₁ -C ₆ ) alkoxy group, (vi) halo (C ₁ -C ₆ ) alkoxy group, (vii) (C ₁ -C ₆ ) alkylthio group, (viii) halo (C ₁ -C ₆ ) An alkylthio group, (ix) (C ₁ -C ₆ ) alkoxycarbonyl group, (x) phenyl group, (xi) 1 may be the same or different and are selected from a halogen atom and a (C ₁ -C ₆ ) alkyl group A substituted phenyl group having the above substituents, and a substituted phenyl group having one or more substituents selected from (xii) (C ₁ -C ₆ ) alkoxyimino (C ₁ -C ₆ ) alkyl groups;
(24e) a heterocyclic group;
(25e) may be the same or different, and (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, v) (C ₁ -C ₆ ) alkoxy group, (vi) halo (C ₁ -C ₆ ) alkoxy group, (vii) (C ₁ -C ₆ ) alkylthio group, (viii) halo (C ₁ -C ₆ ) A substituted heterocyclic group having one or more substituents selected from an alkylthio group, and (ix) (C ₁ -C ₆ ) alkoxycarbonyl group;
(26e) heterocycle-carbonyl group;
(27e) may be the same or different, and (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, ( v) (C ₁ -C ₆ ) alkoxy group, (vi) halo (C ₁ -C ₆ ) alkoxy group, (vii) (C ₁ -C ₆ ) alkylthio group, (viii) halo (C ₁ -C ₆ ) A substituted heterocyclic-carbonyl group having one or more substituents selected from an alkylthio group and (ix) (C ₁ -C ₆ ) alkoxycarbonyl group;
(28e) carboxyl group;
_{(29e) (C 1 -C 6} ) alkoxycarbonyl group;
(30e) a halo (C ₁ -C ₆ ) alkoxycarbonyl group;
(31e) a phenylthio group;
(32e) may be the same or different, and (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, ( v) (C ₁ -C ₆ ) alkoxy group, (vi) halo (C ₁ -C ₆ ) alkoxy group, (vii) (C ₁ -C ₆ ) alkylthio group, (viii) halo (C ₁ -C ₆ ) An alkylthio group, and a substituted phenylthio group having on the ring one or more substituents selected from (ix) (C ₁ -C ₆ ) alkoxycarbonyl groups;
(33e) a phenyl (C ₁ -C ₆ ) alkoxycarbonyl group;
(34e) may be the same or different, and (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, ( v) (C ₁ -C ₆ ) alkoxy group, (vi) halo (C ₁ -C ₆ ) alkoxy group, (vii) (C ₁ -C ₆ ) alkylthio group, (viii) halo (C ₁ -C ₆ ) A substituted phenyl (C ₁ -C ₆ ) alkoxycarbonyl group having one or more substituents selected from an alkylthio group and (ix) (C ₁ -C ₆ ) alkoxycarbonyl group on the ring;
(35e) a phenylamino-carbonyl group;
(36e) may be the same or different, and (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, ( v) (C ₁ -C ₆ ) alkoxy group, (vi) halo (C ₁ -C ₆ ) alkoxy group, (vii) (C ₁ -C ₆ ) alkylthio group, (viii) halo (C ₁ -C ₆ ) A substituted phenylamino-carbonyl group having, on the ring, one or more substituents selected from an alkylthio group and (ix) (C ₁ -C ₆ ) alkoxycarbonyl group;
(37e) _(C 1 -C ₆₎ alkoxyimino _(C 1 -C ₆₎ alkyl group;
(38e) phenyl _(C 1 -C ₆₎ alkoxyimino _(C 1 -C ₆₎ alkyl group; and
(39e) may be the same or different and (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, v) (C ₁ -C ₆ ) alkoxy group, (vi) halo (C ₁ -C ₆ ) alkoxy group, (vii) (C ₁ -C ₆ ) alkylthio group, (viii) halo (C ₁ -C ₆ ) alkylthio group, and _{(ix) (C} 1 -C ₆₎ alkoxy substituted phenyl having one or more substituents selected from a carbonyl group on the ring _(C 1 -C ₆₎ alkoxyimino _(C 1 -C ₆₎ alkyl Indicates a substituent selected from the group, or
Y ¹ and ^{Y 2} and ^{Y 2} and ^{Y 3} together
_{(40e) (C 3 -C 5} ) alkylene group;
_{(41e) (C 3 -C 5} ) alkenylene group;
_{(42e) (C 2 -C 4} ) alkyleneoxy group; or
(43e) A (C ₁ -C ₃ ) alkylenedioxy group optionally substituted by a halogen atom can be shown.
However, N- [2- (3-trifluoromethyl-5-methoxypyrazol-1-yl) ethyl] -2-bromobenzamide is excluded. }
N-2- (substituted pyrazolyl) ethylcarboxamide derivative represented by the formula:

[2] R ¹ is a (2a) (C ₁ -C ₆ ) alkyl group,
R ² is (1a) a hydrogen atom,
The N-2- (substituted pyrazolyl) ethylcarboxamide derivative or a salt thereof according to the above [1], wherein R ³ is (1b) a hydrogen atom;

[3] Ar is (1c) a phenyl group,
X may be the same or different,
(1d) a halogen atom;
(2d) a cyano group;
(3d) a nitro group;
(4d) a (C ₁ -C ₆ ) alkyl group;
(5d) a halo (C ₁ -C ₆ ) alkyl group;
_{(6d) (C 3 -C 6} ) cycloalkyl group;
(7d) a (C ₁ -C ₆ ) alkoxy group;
(8d) a halo (C ₁ -C ₆ ) alkoxy group;
(9d) a (C ₁ -C ₆ ) alkylthio group;
(10d) a halo (C ₁ -C ₆ ) alkylthio group;
(11d) a (C ₁ -C ₆ ) alkoxy (C ₁ -C ₆ ) alkylthio group;
(12d) a (C ₁ -C ₆ ) alkylsulfinyl group;
(13d) a halo (C ₁ -C ₆ ) alkylsulfinyl group;
(14d) a (C ₁ -C ₆ ) alkylsulfonyl group;
(15d) a halo (C ₁ -C ₆ ) alkylsulfonyl group;
(16d) an amino group;
(17d) a mono (C ₁ -C ₆ ) alkylamino group;
(18d) di (C ₁ -C ₆ ) alkylamino groups which may be the same or different;

(19d) piperidino group;
(20d) may be the same or different, (i) (C ₁ -C ₆ ) alkyl group, (ii) halo (C ₁ -C ₆ ) alkyl group, (iii) (C ₁ -C ₆ ) alkoxy group, And (iv) a substituted piperidino group having one or more substituents selected from halo (C ₁ -C ₆ ) alkoxy groups;
(21d) a phenyl group;
(22d) may be the same or different, and (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, ( v) a substituted phenyl group having one or more substituents selected from (C ₁ -C ₆ ) alkoxy groups, and (vi) halo (C ₁ -C ₆ ) alkoxy groups;
(23d) a phenoxy group;
(24d) may be the same or different, and (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, ( v) a (C ₁ -C ₆ ) alkoxy group, and (vi) a substituted phenoxy group having one or more substituents selected from halo (C ₁ -C ₆ ) alkoxy groups;
(25d) a phenyl (C ₁ -C ₆ ) alkyl group;
(26d) may be the same or different, and (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, ( v) a substituted phenyl (C ₁ -C ₆ ) alkyl having on the ring one or more substituents selected from (C ₁ -C ₆ ) alkoxy groups, and (vi) a halo (C ₁ -C ₆ ) alkoxy group A group; and
(27d) a substituent selected from a (C ₁ -C ₆ ) alkoxyimino (C ₁ -C ₆ ) alkyl group,
the N-2- (substituted pyrazolyl) ethylcarboxamide derivative or a salt thereof according to the above [1] or [2], wherein n is an integer of 0 to 3;

[4] Ar is
(2c) (i) pyridyl group, (ii) pyrimidinyl group, (iii) pyrazinyl group, (iv) pyrazolyl group, (v) furyl group, (vi) thienyl group, (viii) isoxazolyl group, (ix) thiazolyl group And (xi) a heterocyclic group selected from thiadiazolyl groups,
X may be the same or different,
(1d) a halogen atom;
(4d) a (C ₁ -C ₆ ) alkyl group;
(5d) a halo (C ₁ -C ₆ ) alkyl group;
_{(6d) (C 3 -C 6} ) cycloalkyl group;
(7d) a (C ₁ -C ₆ ) alkoxy group; or
(9d) The N-2- (substituted pyrazolyl) ethylcarboxamide derivative or a salt thereof according to the above [1] or [2], which is a (C ₁ -C ₆ ) alkylthio group;

[5] Y ¹ , Y ² and Y ³ may be the same or different,
(1e) a hydrogen atom;
(2e) a halogen atom;
(3e) a cyano group;
(4e) a (C ₁ -C ₆ ) alkyl group;
(5e) a halo (C ₁ -C ₆ ) alkyl group;
(6e) a (C ₁ -C ₆ ) alkylcarbonyl group;
(7e) a (C ₁ -C ₆ ) alkoxy group;
(8e) a halo (C ₁ -C ₆ ) alkoxy group;
(9e) a (C ₁ -C ₆ ) alkoxy (C ₁ -C ₆ ) alkyl group;
(10e) a (C ₁ -C ₆ ) alkylthio group;
(11e) a halo (C ₁ -C ₆ ) alkylthio group;
(12e) a (C ₁ -C ₆ ) alkylsulfinyl group;
(13e) a halo (C ₁ -C ₆ ) alkylsulfinyl group;
_{(14e) (C 1 -C 6} ) alkylsulfonyl group;
(15e) a halo (C ₁ -C ₆ ) alkylsulfonyl group;
(16e) an amino group;
(20e) a mono (C ₁ -C ₆ ) alkylamino-carbonyl group;
(21e) di (C ₁ -C ₆ ) alkylamino-carbonyl groups which may be the same or different;

(22e) a phenyl group;
(23e) may be the same or different, (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, ( _{v) (C} 1 -C ₆₎ alkoxy group, (vi) halo _(C 1 -C ₆₎ alkoxy groups, _{(vii) (C} 1 -C ₆₎ alkylthio group, (ix) _(C 1 -C ₆₎ alkoxy A carbonyl group, (x) a phenyl group, (xi) a substituted phenyl group which may be the same or different and has one or more substituents selected from a halogen atom and a (C ₁ -C ₆ ) alkyl group, and (xii) A substituted phenyl group having one or more substituents selected from a (C ₁ -C ₆ ) alkoxyimino (C ₁ -C ₆ ) alkyl group;
(24e) a heterocyclic group;
(25e) may be the same or different, and (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, v) (C ₁ -C ₆ ) alkoxy group, (vi) halo (C ₁ -C ₆ ) alkoxy group, (vii) (C ₁ -C ₆ ) alkylthio group, (viii) halo (C ₁ -C ₆ ) A substituted heterocyclic group having one or more substituents selected from an alkylthio group, and (ix) (C ₁ -C ₆ ) alkoxycarbonyl group;
(26e) heterocycle-carbonyl group;
(27e) may be the same or different, and (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, ( v) (C ₁ -C ₆ ) alkoxy group, (vi) halo (C ₁ -C ₆ ) alkoxy group, (vii) (C ₁ -C ₆ ) alkylthio group, (viii) halo (C ₁ -C ₆ ) A substituted heterocyclic-carbonyl group having one or more substituents selected from an alkylthio group and (ix) (C ₁ -C ₆ ) alkoxycarbonyl group;
(28e) carboxyl group;
_{(29e) (C 1 -C 6} ) alkoxycarbonyl group;
(30e) a halo (C ₁ -C ₆ ) alkoxycarbonyl group;
(31e) a phenylthio group;
(32e) may be the same or different, and (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, ( v) (C ₁ -C ₆ ) alkoxy group, (vi) halo (C ₁ -C ₆ ) alkoxy group, (vii) (C ₁ -C ₆ ) alkylthio group, (viii) halo (C ₁ -C ₆ ) An alkylthio group, and a substituted phenylthio group having on the ring one or more substituents selected from (ix) (C ₁ -C ₆ ) alkoxycarbonyl groups;
(33e) a phenyl (C ₁ -C ₆ ) alkoxycarbonyl group;
(34e) may be the same or different, and (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, ( v) (C ₁ -C ₆ ) alkoxy group, (vi) halo (C ₁ -C ₆ ) alkoxy group, (vii) (C ₁ -C ₆ ) alkylthio group, (viii) halo (C ₁ -C ₆ ) A substituted phenyl (C ₁ -C ₆ ) alkoxycarbonyl group having one or more substituents selected from an alkylthio group and (ix) (C ₁ -C ₆ ) alkoxycarbonyl group on the ring;
(35e) a phenylamino-carbonyl group;
(36e) may be the same or different, and (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, ( v) (C ₁ -C ₆ ) alkoxy group, (vi) halo (C ₁ -C ₆ ) alkoxy group, (vii) (C ₁ -C ₆ ) alkylthio group, (viii) halo (C ₁ -C ₆ ) A substituted phenylamino-carbonyl group having, on the ring, one or more substituents selected from an alkylthio group and (ix) (C ₁ -C ₆ ) alkoxycarbonyl group;
(37e) _(C 1 -C ₆₎ alkoxyimino _(C 1 -C ₆₎ alkyl group;
(38e) phenyl _(C 1 -C ₆₎ alkoxyimino _(C 1 -C ₆₎ alkyl group; and
(39e) may be the same or different and (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, v) (C ₁ -C ₆ ) alkoxy group, (vi) halo (C ₁ -C ₆ ) alkoxy group, (vii) (C ₁ -C ₆ ) alkylthio group, (viii) halo (C ₁ -C ₆ ) alkylthio group, and _{(ix) (C} 1 -C ₆₎ alkoxy substituted phenyl having one or more substituents selected from a carbonyl group on the ring _(C 1 -C ₆₎ alkoxyimino _(C 1 -C ₆₎ alkyl The N-2- (substituted pyrazolyl) ethylcarboxamide derivative or a salt thereof according to any one of the above [1] to [4], which is a substituent selected from a group;

[6] A pest control agent comprising the N-2- (substituted pyrazolyl) ethylcarboxamide derivative or a salt thereof according to any one of [1] to [5] as an active ingredient;
[7] The pest control agent according to the above [6], which is a plant disease control agent;
[8] The pest control agent according to [6], which is a nematicide;
[9] Pest control, characterized by treating an effective amount of the pest control agent according to any one of [6] to [8] above with a target crop plant or soil used for cultivation of the plant Method; [10] General formula (III)

(Wherein R ¹ and R ² may be the same or different,
(1a) a hydrogen atom; or
(2a) represents a (C ₁ -C ₆ ) alkyl group. R ¹ and R ² are together
(3a) (C ₃ -C ₆ ) cycloalkane may be formed.

R ³ is
(1b) a hydrogen atom;
(2b) a (C ₁ -C ₆ ) alkyl group;
(3b) a (C ₁ -C ₆ ) alkoxy (C ₁ -C ₆ ) alkyl group;
(4b) a (C ₁ -C ₆ ) alkylcarbonyl group; or
(5b) represents a (C ₁ -C ₆ ) alkoxycarbonyl group.

Y ¹ , Y ² and Y ³ may be the same or different,
(1e) a hydrogen atom;
(2e) a halogen atom;
(3e) a cyano group;
(4e) a (C ₁ -C ₆ ) alkyl group;
(5e) a halo (C ₁ -C ₆ ) alkyl group;
(6e) a (C ₁ -C ₆ ) alkylcarbonyl group;
(7e) a (C ₁ -C ₆ ) alkoxy group;
(8e) a halo (C ₁ -C ₆ ) alkoxy group;
(9e) a (C ₁ -C ₆ ) alkoxy (C ₁ -C ₆ ) alkyl group;
(10e) a (C ₁ -C ₆ ) alkylthio group;
(11e) a halo (C ₁ -C ₆ ) alkylthio group;
(12e) a (C ₁ -C ₆ ) alkylsulfinyl group;
(13e) a halo (C ₁ -C ₆ ) alkylsulfinyl group;
_{(14e) (C 1 -C 6} ) alkylsulfonyl group;
(15e) a halo (C ₁ -C ₆ ) alkylsulfonyl group;
(16e) an amino group;
(17e) a mono (C ₁ -C ₆ ) alkylamino group;
(18e) di (C ₁ -C ₆ ) alkylamino groups which may be the same or different;
(19e) amino-carbonyl group;
(20e) a mono (C ₁ -C ₆ ) alkylamino-carbonyl group;
(21e) di (C ₁ -C ₆ ) alkylamino-carbonyl groups which may be the same or different;

(22e) a phenyl group;
(23e) may be the same or different, (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, ( v) (C ₁ -C ₆ ) alkoxy group, (vi) halo (C ₁ -C ₆ ) alkoxy group, (vii) (C ₁ -C ₆ ) alkylthio group, (viii) halo (C ₁ -C ₆ ) An alkylthio group, (ix) (C ₁ -C ₆ ) alkoxycarbonyl group, (x) phenyl group, (xi) 1 may be the same or different and are selected from a halogen atom and a (C ₁ -C ₆ ) alkyl group A substituted phenyl group having the above substituents, and a substituted phenyl group having one or more substituents selected from (xii) (C ₁ -C ₆ ) alkoxyimino (C ₁ -C ₆ ) alkyl groups;
(24e) a heterocyclic group;
(25e) may be the same or different, and (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, v) (C ₁ -C ₆ ) alkoxy group, (vi) halo (C ₁ -C ₆ ) alkoxy group, (vii) (C ₁ -C ₆ ) alkylthio group, (viii) halo (C ₁ -C ₆ ) A substituted heterocyclic group having one or more substituents selected from an alkylthio group, and (ix) (C ₁ -C ₆ ) alkoxycarbonyl group;
(26e) heterocycle-carbonyl group;
(27e) may be the same or different, and (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, ( v) (C ₁ -C ₆ ) alkoxy group, (vi) halo (C ₁ -C ₆ ) alkoxy group, (vii) (C ₁ -C ₆ ) alkylthio group, (viii) halo (C ₁ -C ₆ ) A substituted heterocyclic-carbonyl group having one or more substituents selected from an alkylthio group and (ix) (C ₁ -C ₆ ) alkoxycarbonyl group;
(28e) carboxyl group;
_{(29e) (C 1 -C 6} ) alkoxycarbonyl group;
(30e) a halo (C ₁ -C ₆ ) alkoxycarbonyl group;
(31e) a phenylthio group;
(32e) may be the same or different, and (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, ( v) (C ₁ -C ₆ ) alkoxy group, (vi) halo (C ₁ -C ₆ ) alkoxy group, (vii) (C ₁ -C ₆ ) alkylthio group, (viii) halo (C ₁ -C ₆ ) An alkylthio group, and a substituted phenylthio group having on the ring one or more substituents selected from (ix) (C ₁ -C ₆ ) alkoxycarbonyl groups;
(33e) a phenyl (C ₁ -C ₆ ) alkoxycarbonyl group;
(34e) may be the same or different, and (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, ( v) (C ₁ -C ₆ ) alkoxy group, (vi) halo (C ₁ -C ₆ ) alkoxy group, (vii) (C ₁ -C ₆ ) alkylthio group, (viii) halo (C ₁ -C ₆ ) A substituted phenyl (C ₁ -C ₆ ) alkoxycarbonyl group having one or more substituents selected from an alkylthio group and (ix) (C ₁ -C ₆ ) alkoxycarbonyl group on the ring;
(35e) a phenylamino-carbonyl group;
(36e) may be the same or different, and (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, ( v) (C ₁ -C ₆ ) alkoxy group, (vi) halo (C ₁ -C ₆ ) alkoxy group, (vii) (C ₁ -C ₆ ) alkylthio group, (viii) halo (C ₁ -C ₆ ) A substituted phenylamino-carbonyl group having, on the ring, one or more substituents selected from an alkylthio group and (ix) (C ₁ -C ₆ ) alkoxycarbonyl group;
(37e) _(C 1 -C ₆₎ alkoxyimino _(C 1 -C ₆₎ alkyl group;
(38e) phenyl _(C 1 -C ₆₎ alkoxyimino _(C 1 -C ₆₎ alkyl group; and
(39e) may be the same or different and (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, v) (C ₁ -C ₆ ) alkoxy group, (vi) halo (C ₁ -C ₆ ) alkoxy group, (vii) (C ₁ -C ₆ ) alkylthio group, (viii) halo (C ₁ -C ₆ ) alkylthio group, and _{(ix) (C} 1 -C ₆₎ alkoxy substituted phenyl having one or more substituents selected from a carbonyl group on the ring _(C 1 -C ₆₎ alkoxyimino _(C 1 -C ₆₎ alkyl Indicates a substituent selected from the group, or
Y ¹ and ^{Y 2} and ^{Y 2} and ^{Y 3} together
_{(40e) (C 3 -C 5} ) alkylene group;
_{(41e) (C 3 -C 5} ) alkenylene group;
_{(42e) (C 2 -C 4} ) alkyleneoxy group; or
(43e) A (C ₁ -C ₃ ) alkylenedioxy group optionally substituted by a halogen atom can be shown. ) Or a salt thereof;

[11] R ¹ is a (C ₁ -C ₆ ) alkyl group,
R ² is a hydrogen atom,
Y ¹ , Y ² and Y ³ may be the same or different,
(1e) a hydrogen atom;
(2e) a halogen atom;
(3e) a cyano group;
(4e) a (C ₁ -C ₆ ) alkyl group;
(5e) a halo (C ₁ -C ₆ ) alkyl group;
(6e) a (C ₁ -C ₆ ) alkylcarbonyl group;
(7e) a (C ₁ -C ₆ ) alkoxy group;
(8e) a halo (C ₁ -C ₆ ) alkoxy group;
(9e) a (C ₁ -C ₆ ) alkoxy (C ₁ -C ₆ ) alkyl group;
(10e) a (C ₁ -C ₆ ) alkylthio group;
(11e) a halo (C ₁ -C ₆ ) alkylthio group;
(12e) a (C ₁ -C ₆ ) alkylsulfinyl group;
(13e) a halo (C ₁ -C ₆ ) alkylsulfinyl group;
_{(14e) (C 1 -C 6} ) alkylsulfonyl group;
(15e) a halo (C ₁ -C ₆ ) alkylsulfonyl group;
(16e) an amino group;
(20e) a mono (C ₁ -C ₆ ) alkylamino-carbonyl group;
(21e) di (C ₁ -C ₆ ) alkylamino-carbonyl groups which may be the same or different;

(22e) a phenyl group;
(23e) may be the same or different, (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, ( _{v) (C} 1 -C ₆₎ alkoxy group, (vi) halo _(C 1 -C ₆₎ alkoxy groups, _{(vii) (C} 1 -C ₆₎ alkylthio group, (ix) _(C 1 -C ₆₎ alkoxy A carbonyl group, (x) a phenyl group, (xi) a substituted phenyl group which may be the same or different and has one or more substituents selected from a halogen atom and a (C ₁ -C ₆ ) alkyl group, and (xii) A substituted phenyl group having one or more substituents selected from a (C ₁ -C ₆ ) alkoxyimino (C ₁ -C ₆ ) alkyl group;
(24e) a heterocyclic group;
(25e) may be the same or different, and (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, v) (C ₁ -C ₆ ) alkoxy group, (vi) halo (C ₁ -C ₆ ) alkoxy group, (vii) (C ₁ -C ₆ ) alkylthio group, (viii) halo (C ₁ -C ₆ ) A substituted heterocyclic group having one or more substituents selected from an alkylthio group, and (ix) (C ₁ -C ₆ ) alkoxycarbonyl group;
(26e) heterocycle-carbonyl group;
(27e) may be the same or different, and (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, ( v) (C ₁ -C ₆ ) alkoxy group, (vi) halo (C ₁ -C ₆ ) alkoxy group, (vii) (C ₁ -C ₆ ) alkylthio group, (viii) halo (C ₁ -C ₆ ) A substituted heterocyclic-carbonyl group having one or more substituents selected from an alkylthio group and (ix) (C ₁ -C ₆ ) alkoxycarbonyl group;
(28e) carboxyl group;
_{(29e) (C 1 -C 6} ) alkoxycarbonyl group;
(30e) a halo (C ₁ -C ₆ ) alkoxycarbonyl group;
(31e) a phenylthio group;
(32e) may be the same or different, and (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, ( v) (C ₁ -C ₆ ) alkoxy group, (vi) halo (C ₁ -C ₆ ) alkoxy group, (vii) (C ₁ -C ₆ ) alkylthio group, (viii) halo (C ₁ -C ₆ ) An alkylthio group, and a substituted phenylthio group having on the ring one or more substituents selected from (ix) (C ₁ -C ₆ ) alkoxycarbonyl groups;
(33e) a phenyl (C ₁ -C ₆ ) alkoxycarbonyl group;
(34e) may be the same or different, and (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, ( v) (C ₁ -C ₆ ) alkoxy group, (vi) halo (C ₁ -C ₆ ) alkoxy group, (vii) (C ₁ -C ₆ ) alkylthio group, (viii) halo (C ₁ -C ₆ ) A substituted phenyl (C ₁ -C ₆ ) alkoxycarbonyl group having one or more substituents selected from an alkylthio group and (ix) (C ₁ -C ₆ ) alkoxycarbonyl group on the ring;
(35e) a phenylamino-carbonyl group;
(36e) may be the same or different, and (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, ( v) (C ₁ -C ₆ ) alkoxy group, (vi) halo (C ₁ -C ₆ ) alkoxy group, (vii) (C ₁ -C ₆ ) alkylthio group, (viii) halo (C ₁ -C ₆ ) A substituted phenylamino-carbonyl group having, on the ring, one or more substituents selected from an alkylthio group and (ix) (C ₁ -C ₆ ) alkoxycarbonyl group;
(37e) _(C 1 -C ₆₎ alkoxyimino _(C 1 -C ₆₎ alkyl group;
(38e) phenyl _(C 1 -C ₆₎ alkoxyimino _(C 1 -C ₆₎ alkyl group; and
(39e) may be the same or different and (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, v) (C ₁ -C ₆ ) alkoxy group, (vi) halo (C ₁ -C ₆ ) alkoxy group, (vii) (C ₁ -C ₆ ) alkylthio group, (viii) halo (C ₁ -C ₆ ) alkylthio group, and _{(ix) (C} 1 -C ₆₎ alkoxy substituted phenyl having one or more substituents selected from a carbonyl group on the ring _(C 1 -C ₆₎ alkoxyimino _(C 1 -C ₆₎ alkyl A pyrazolylethylamine derivative or a salt thereof according to the above [10], which is a substituent selected from a group;
Etc.

  The present invention provides a compound having excellent performance as compared with the prior art, particularly a plant disease control agent having a low bactericidal spectrum and a wide bactericidal spectrum and nematicidal activity.

  The definition of general formula (I) of the N-2- (substituted pyrazolyl) ethylcarboxamide derivative of the present invention will be described below.

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

“(C ₁ -C ₆ ) alkyl group” means, for example, methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, isobutyl group, secondary butyl group, tertiary butyl group, normal pentyl group, neopentyl group Represents a linear or branched alkyl group having 1 to 6 carbon atoms, such as a normal hexyl group.

The “halo (C ₁ -C ₆ ) alkyl group” refers to a linear or branched alkyl group having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different, Examples thereof include a trifluoromethyl group, a difluoromethyl group, a perfluoroethyl group, a perfluoroisopropyl group, a chloromethyl group, a bromomethyl group, a 1-bromoethyl group, and a 2,3-dibromopropyl group.

The “(C ₃ -C ₆ ) cycloalkyl group” refers to a cycloalkyl group having 3 to 6 carbon atoms such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group and the like.

“(C ₁ -C ₆ ) alkoxy group” means, for example, methoxy group, ethoxy group, normal propoxy group, isopropoxy group, normal butoxy group, secondary butoxy group, tertiary butoxy group, normal pentyloxy group, isopentyloxy A linear or branched alkoxy group having 1 to 6 carbon atoms such as a group, a neopentyloxy group, and a normal hexyloxy group;

The “halo (C ₁ -C ₆ ) alkoxy group” refers to a linear or branched alkoxy group having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different, For example, trifluoromethoxy group, difluoromethoxy group, perfluoroethoxy group, perfluoroisopropoxy group, chloromethoxy group, bromomethoxy group, 1-bromoethoxy group, 2,3-dibromopropoxy group and the like are shown.

“(C ₁ -C ₆ ) alkylthio group” means, for example, methylthio group, ethylthio group, normal propylthio group, isopropylthio group, normal butylthio group, secondary butylthio group, tertiary butylthio group, normal pentylthio group , A linear or branched alkylthio group having 1 to 6 carbon atoms, such as an isopentylthio group and a normal hexylthio group.

The “halo (C ₁ -C ₆ ) alkylthio group” refers to a linear or branched alkylthio group having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different, For example, trifluoromethylthio group, difluoromethylthio group, perfluoroethylthio group, perfluoroisopropylthio group, chloromethylthio group, bromomethylthio group, 1-bromoethylthio group, 2,3-dibromopropylthio group and the like are shown.

“(C ₁ -C ₆ ) alkylsulfinyl group” means, for example, methylsulfinyl group, ethylsulfinyl group, normal propylsulfinyl group, isopropylsulfinyl group, normal butylsulfinyl group, secondary butylsulfinyl group, tertiary butylsulfinyl group, normal A linear or branched alkylsulfinyl group having 1 to 6 carbon atoms, such as a pentylsulfinyl group, an isopentylsulfinyl group, and a normal hexylsulfinyl group.

The “halo (C ₁ -C ₆ ) alkylsulfinyl group” refers to a linear or branched alkylsulfinyl group having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different. For example, trifluoromethylsulfinyl group, difluoromethylsulfinyl group, perfluoroethylsulfinyl group, perfluoroisopropylsulfinyl group, chloromethylsulfinyl group, bromomethylsulfinyl group, 1-bromoethylsulfinyl group, 2,3-dibromopropylsulfinyl Group etc. are shown.

“(C ₁ -C ₆ ) alkylsulfonyl group” means, for example, methylsulfonyl group, ethylsulfonyl group, normalpropylsulfonyl group, isopropylsulfonyl group, normalbutylsulfonyl group, secondary butylsulfonyl group, tertiary butylsulfonyl group, normal A linear or branched alkylsulfonyl group having 1 to 6 carbon atoms such as a pentylsulfonyl group, an isopentylsulfonyl group, and a normal hexylsulfonyl group is shown.

The “halo (C ₁ -C ₆ ) alkylsulfonyl group” is a linear or branched alkylsulfonyl group having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different. For example, trifluoromethylsulfonyl group, difluoromethylsulfonyl group, perfluoroethylsulfonyl group, perfluoroisopropylsulfonyl group, chloromethylsulfonyl group, bromomethylsulfonyl group, 1-bromoethylsulfonyl group, 2,3-dibromopropylsulfonyl Group etc. are shown.

“(C ₁ -C ₆ ) alkylcarbonyl group” means, for example, a straight chain such as methylcarbonyl group (acetyl group), ethylcarbonyl group, normal propylcarbonyl group, isopropylcarbonyl group, normal butylcarbonyl group, tertiary butylcarbonyl group, etc. A chain or branched alkyl-carbonyl group having 1 to 6 carbon atoms is shown.

The “(C ₁ -C ₆ ) alkoxycarbonyl group” is a straight chain or branched chain such as a methoxycarbonyl group, an ethoxycarbonyl group, a normal propoxycarbonyl group, an isopropoxycarbonyl group, a normal butoxycarbonyl group, a tertiary butoxycarbonyl group, etc. A chain-like alkoxy-carbonyl group having 1 to 6 carbon atoms is shown.

“(C ₁ -C ₆ ) alkoxyimino (C ₁ -C ₆ ) alkyl group” means, for example, a straight chain such as a methoxyiminomethyl group, an ethoxyiminomethyl group, a normal propoxyiminomethyl group, an isopropoxyiminoethyl group or the like A branched chain alkoxy group having 1 to 6 carbon atoms (C ₁ -C ₆ ) alkyl group is shown.

Examples of the “(C ₃ -C ₆ ) cycloalkane” formed by combining R ¹ and R ² include cyclopropane, cyclobutane, cyclopentane, cyclohexane and the like.

Examples of the “(C ₃ -C ₅ ) alkylene group” include trimethylene group, tetramethylene group, pentamethylene group and the like.

As the _"(C 3 -C ₅₎ alkenylene _{group", -CH 2 -CH = CH -,} - CH 2 -CH 2 -CH = CH -, - CH = CH-CH = CH -, - CH 2 -CH _{2 -CH 2 -CH = CH -,} - CH 2 -CH 2 -CH = CH-CH 2 -, - CH = CH-CH = CH-CH 2 - , and the like.

The _"(C 2 -C ₄₎ alkyleneoxy _{group", -CH 2 -CH 2 -O -,} - CH 2 -CH 2 -CH 2 -O -, - CH 2 -CH 2 -CH 2 -CH 2 -O- etc. are mentioned.

Examples of the “(C ₁ -C ₃ ) alkylenedioxy group optionally substituted by a halogen atom” include —O—CH ₂ —O—, —O—CH ₂ —CH ₂ —O—, —O—CH. ₂ -CH ₂ -CH ₂ -O-, etc. alkylenedioxy group having 1 to 3 carbon atoms; indicates the alkylenedioxy group substituted by and identical or different may be one or more halogen atoms, e.g., - _{O-CF 2 -O -, -} O-CF 2 -CF 2 -O -, - shows the _O-CCl 2 -O- and the like.

“Mono (C ₁ -C ₆ ) alkylamino group” means, for example, a straight chain such as a methylamino group, an ethylamino group, a normalpropylamino group, an isopropylamino group, a butylamino group, a pentylamino group, or a hexylamino group. A branched alkylamino group having 1 to 6 carbon atoms is shown.

“Di (C ₁ -C ₆ ) alkylamino group which may be the same or different” means, for example, dimethylamino group, diethylamino group, dinormalpropylamino group, diisopropylamino group, N-methyl-N-ethylamino group, N-methyl-N-isopropylamino group, N-ethyl-N-hexylamino and the like, which may be the same or different, an amino group having two linear or branched alkyl groups having 1 to 6 carbon atoms Indicates.

“Mono (C ₁ -C ₆ ) alkylamino-carbonyl group” means, for example, methylamino-carbonyl group, ethylamino-carbonyl group, normalpropylamino-carbonyl group, isopropylamino-carbonyl group, butylamino-carbonyl group, A linear or branched alkylamino-carbonyl group having 1 to 6 carbon atoms such as a pentylamino-carbonyl group and a hexylamino-carbonyl group is shown.

Examples of the “di (C ₁ -C ₆ ) alkylamino-carbonyl group which may be the same or different” include, for example, a dimethylamino-carbonyl group, a diethylamino-carbonyl group, a dinormalpropylamino-carbonyl group, a diisopropylamino-carbonyl group, N-methyl-N-ethylamino-carbonyl group, N-methyl-N-isopropylamino-carbonyl group, N-ethyl-N-hexylamino-carbonyl, etc., which may be the same or different, may be linear or branched An amino-carbonyl group having two alkyl groups having 1 to 6 carbon atoms is shown.

“Heterocycle” refers to a 5- or 6-membered heterocyclic group having one or more heteroatoms selected from an oxygen atom, a sulfur atom and a nitrogen atom. For example, a furyl group (1- or 2-furyl group) , Tetrahydrofuryl group (1- or 2-tetrahydrofuryl group), thienyl group (1- or 2-thienyl group), tetrahydrothienyl group (1- or 2-tetrahydrothienyl group), pyrrolyl group (1-, 2- or 3-pyrrolyl group), pyrrolidinyl group (1-, 2- or 3-pyrrolidinyl group), imidazolyl group (1-, 2- or 4-imidazolyl group), imidazolidinyl group, pyrazolyl group (1-, 3- or 4- Pyrazolyl group), pyrazolidinyl group, oxazolyl group (2-, 4- or 5-oxazolyl group), oxazolidinyl group, thiazolyl group (2-, 4- or 5-thiazolyl group) , Thiazolidinyl group, isoxazolyl group (3-, 4- or 5-isoxazolyl group), isoxazolidinyl group, isothiazolyl group (3-, 4- or 5-isothiazolyl group), isothiazolidinyl group, triazolyl group ( 1,2,3-triazol-1-, 4- or 5-yl group, 1,2,4-triazol-1-, 3- or 4-yl group), triazolidinyl group, oxadiazolyl group (1,2,3 -Oxadiazol-4- or 5-yl group, 1,2,4-oxadiazol-3- or 4-yl group), thiadiazolyl group (1,2,3-thiadiazol-4- or 5-yl group) 1,2,4-thiadiazol-3- or 4-yl group), pyridyl group (2-, 3- or 4-pyridyl group), pyridine-N-oxide group, pyrimidinyl group (2-, 4- or 5) - Jiniru group), pyrazinyl group (2-pyrazinyl group), tetrahydropyranyl group, tetrahydrothiopyranyl group, and the like.
The heterocyclic group represented by Ar is selected from a pyridyl group, pyrimidinyl group, pyrazinyl group, pyrazolyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isoxazolyl group, and thiadiazolyl group.

In addition, expressions such as “(C ₁ -C ₆ )”, “(C ₂ -C ₆ )”, and “(C ₃ -C ₆ )” indicate the range of the number of carbon atoms of various substituents. Further, it is possible to show the definition of groups in which the substituent is linked, for example, "(C 1 _{-C 6)} alkoxy (C 1 _{-C 6)} alkyl group" for straight-chain or branched It indicates that the alkoxy group having 1 to 6 carbon atoms is bonded to a linear or branched alkyl group having 1 to 6 carbon atoms, such as a methoxymethyl group, 1- or 2-methoxyethyl group, 1 Examples include-, 2- or 3-methoxypropyl group, ethoxymethyl group, 1- or 2-ethoxyethyl group, 1-, 2- or 3-ethoxypropyl group.
Similarly, the “(C ₁ -C ₆ ) alkoxy (C ₁ -C ₆ ) alkylthio group” includes a methoxymethylthio group, 1- or 2-methoxyethylthio group, 1-, 2- or 3-methoxypropylthio group. Group, ethoxymethylthio group, 1- or 2-ethoxyethylthio group, 1-, 2- or 3-ethoxypropylthio group and the like.

  Of the N-2- (substituted pyrazolyl) ethylcarboxamide derivatives represented by the general formula (I), N- [2- (3-trifluoromethyl-5-methoxypyrazol-1-yl) ethyl] -2-bromo Benzamide is excluded from the compounds of the present invention.

  Examples of the salt of the N-2- (substituted pyrazolyl) ethylcarboxamide derivative represented by the general formula (I) of the present invention include inorganic acid salts such as hydrochloride, sulfate, nitrate, and phosphate, acetate, and fumaric acid. Organic acid salts such as salt, maleate, oxalate, methanesulfonate, benzenesulfonate, paratoluenesulfonate, and inorganic or organic bases such as sodium ion, potassium ion, calcium ion, trimethylammonium salt Examples of these salts can be exemplified.

The N-2- (substituted pyrazolyl) ethylcarboxamide 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 kinds of optical Isomers and diastereomers may exist, and the present invention includes all of the optical isomers and mixtures containing them in an arbitrary ratio.
In addition, the N-2- (substituted pyrazolyl) ethylcarboxamide derivative represented by the general formula (I) of the present invention includes two geometric isomers derived from a carbon-carbon double bond in the structural formula. In some cases, the present invention also encompasses all geometric isomers and mixtures containing them in any proportion.

In the N-2- (substituted pyrazolyl) ethylcarboxamide derivative represented by the general formula (I) of the present invention,
R ¹ and R ² are preferably
(1a) a hydrogen atom; or (2a) a (C ₁ -C ₆ ) alkyl group (more preferably a methyl group; or an ethyl group).
At least one of R ¹ and R ² is more preferably a hydrogen atom, and the (S) isomer that is one enantiomer of the optically active substance that accompanies it is more preferred.

R ³ is preferably
(1b) a hydrogen atom;
(3b) a (C ₁ -C ₆ ) alkoxy (C ₁ -C ₆ ) alkyl group;
(4b) a (C ₁ -C ₆ ) alkylcarbonyl group; or
(5b) (C ₁ -C ₆ ) alkoxycarbonyl group, more preferably a hydrogen atom.

Ar is preferably
(1c) phenyl group; or (2c) a heterocyclic group selected from a pyridyl group, pyrimidinyl group, pyrazinyl group, pyrazolyl group, furyl group, thienyl group, isoxazolyl group, thiazolyl group, and thiadiazolyl group (more preferably, a pyridyl group) Or a pyrazolyl group), particularly preferably a phenyl group.

When Ar is a phenyl group, X is preferably
(1d) a halogen atom;
(2d) a cyano group;
(3d) a nitro group;
(4d) a (C ₁ -C ₆ ) alkyl group;
(5d) a halo (C ₁ -C ₆ ) alkyl group;
_{(6d) (C 3 -C 6} ) cycloalkyl group;
(7d) a (C ₁ -C ₆ ) alkoxy group;
(8d) a halo (C ₁ -C ₆ ) alkoxy group;
(9d) a (C ₁ -C ₆ ) alkylthio group;
(10d) a halo (C ₁ -C ₆ ) alkylthio group;
(11d) a (C ₁ -C ₆ ) alkoxy (C ₁ -C ₆ ) alkylthio group;
(12d) a (C ₁ -C ₆ ) alkylsulfinyl group;
(13d) a halo (C ₁ -C ₆ ) alkylsulfinyl group;
(14d) a (C ₁ -C ₆ ) alkylsulfonyl group;
(15d) a halo (C ₁ -C ₆ ) alkylsulfonyl group;
(16d) an amino group;
(17d) a mono (C ₁ -C ₆ ) alkylamino group;
(18d) di (C ₁ -C ₆ ) alkylamino groups which may be the same or different;
(19d) piperidino group;
(20d) may be the same or different, (i) (C ₁ -C ₆ ) alkyl group, (ii) halo (C ₁ -C ₆ ) alkyl group, (iii) (C ₁ -C ₆ ) alkoxy group, And (iv) a substituted piperidino group having one or more substituents selected from halo (C ₁ -C ₆ ) alkoxy groups;
(21d) a phenyl group;
(22d) may be the same or different, and (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, ( v) a substituted phenyl group having one or more substituents selected from (C ₁ -C ₆ ) alkoxy groups, and (vi) halo (C ₁ -C ₆ ) alkoxy groups;
(23d) a phenoxy group;
(24d) may be the same or different, and (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, ( v) a (C ₁ -C ₆ ) alkoxy group, and (vi) a substituted phenoxy group having one or more substituents selected from halo (C ₁ -C ₆ ) alkoxy groups;
(25d) a phenyl (C ₁ -C ₆ ) alkyl group;
(26d) may be the same or different, and (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, ( v) a substituted phenyl (C ₁ -C ₆ ) alkyl having one or more substituents selected from a (C ₁ -C ₆ ) alkoxy group and (vi) a halo (C ₁ -C ₆ ) alkoxy group on the ring Group; or
(27d) a (C ₁ -C ₆ ) alkoxyimino (C ₁ -C ₆ ) alkyl group.

When Ar is a heterocyclic group, X is preferably
(1d) a halogen atom;
(4d) a (C ₁ -C ₆ ) alkyl group;
(5d) a halo (C ₁ -C ₆ ) alkyl group;
_{(6d) (C 3 -C 6} ) cycloalkyl group;
(7d) a (C ₁ -C ₆ ) alkoxy group; or
(9d) a (C ₁ -C ₆ ) alkylthio group, particularly preferably
(1d) a halogen atom; or (5d) a halo (C ₁ -C ₆ ) alkyl group.
n is preferably an integer of 0 to 3, more preferably an integer of 1 to 3.

Y ¹ , Y ² and Y ³ are preferably
(1e) a hydrogen atom;
(2e) a halogen atom;
(3e) a cyano group;
(4e) a (C ₁ -C ₆ ) alkyl group;
(5e) a halo (C ₁ -C ₆ ) alkyl group;
(6e) a (C ₁ -C ₆ ) alkylcarbonyl group;
(7e) a (C ₁ -C ₆ ) alkoxy group;
(8e) a halo (C ₁ -C ₆ ) alkoxy group;
(9e) a (C ₁ -C ₆ ) alkoxy (C ₁ -C ₆ ) alkyl group;
(10e) a (C ₁ -C ₆ ) alkylthio group;
(11e) a halo (C ₁ -C ₆ ) alkylthio group;
(12e) a (C ₁ -C ₆ ) alkylsulfinyl group;
(13e) a halo (C ₁ -C ₆ ) alkylsulfinyl group;
_{(14e) (C 1 -C 6} ) alkylsulfonyl group;
(15e) a halo (C ₁ -C ₆ ) alkylsulfonyl group;
(16e) an amino group;
(20e) a mono (C ₁ -C ₆ ) alkylamino-carbonyl group;
(21e) di (C ₁ -C ₆ ) alkylamino-carbonyl groups which may be the same or different;
(22e) a phenyl group;
(23e) may be the same or different, (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, ( _{v) (C} 1 -C ₆₎ alkoxy group, (vi) halo _(C 1 -C ₆₎ alkoxy groups, _{(vii) (C} 1 -C ₆₎ alkylthio group, (ix) _(C 1 -C ₆₎ alkoxy A carbonyl group, (x) a phenyl group, (xi) a substituted phenyl group which may be the same or different and has one or more substituents selected from a halogen atom and a (C ₁ -C ₆ ) alkyl group, and (xii) A substituted phenyl group having one or more substituents selected from a (C ₁ -C ₆ ) alkoxyimino (C ₁ -C ₆ ) alkyl group;
(24e) a heterocyclic group;
(25e) may be the same or different, and (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, v) (C ₁ -C ₆ ) alkoxy group, (vi) halo (C ₁ -C ₆ ) alkoxy group, (vii) (C ₁ -C ₆ ) alkylthio group, (viii) halo (C ₁ -C ₆ ) A substituted heterocyclic group having one or more substituents selected from an alkylthio group, and (ix) (C ₁ -C ₆ ) alkoxycarbonyl group;
(26e) heterocycle-carbonyl group;
(27e) may be the same or different, and (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, ( v) (C ₁ -C ₆ ) alkoxy group, (vi) halo (C ₁ -C ₆ ) alkoxy group, (vii) (C ₁ -C ₆ ) alkylthio group, (viii) halo (C ₁ -C ₆ ) A substituted heterocyclic-carbonyl group having one or more substituents selected from an alkylthio group and (ix) (C ₁ -C ₆ ) alkoxycarbonyl group;
(28e) carboxyl group;
_{(29e) (C 1 -C 6} ) alkoxycarbonyl group;
(30e) a halo (C ₁ -C ₆ ) alkoxycarbonyl group;
(33e) a phenyl (C ₁ -C ₆ ) alkoxycarbonyl group;
(31e) a phenylthio group;
(32e) may be the same or different, and (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, ( v) (C ₁ -C ₆ ) alkoxy group, (vi) halo (C ₁ -C ₆ ) alkoxy group, (vii) (C ₁ -C ₆ ) alkylthio group, (viii) halo (C ₁ -C ₆ ) An alkylthio group, and a substituted phenylthio group having on the ring one or more substituents selected from (ix) (C ₁ -C ₆ ) alkoxycarbonyl groups;
(34e) may be the same or different, and (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, ( _{v) (C} 1 -C ₆₎ alkoxy group, (vi) halo _(C 1 -C ₆₎ alkoxy groups, _{(vii) (C} 1 -C ₆₎ alkylthio group, (viii) halo _(C 1 _-C 6) A substituted phenyl (C ₁ -C ₆ ) alkoxycarbonyl group having one or more substituents selected from an alkylthio group and (ix) (C ₁ -C ₆ ) alkoxycarbonyl group on the ring;
(35e) a phenylamino-carbonyl group;
(36e) may be the same or different, and (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, ( v) (C ₁ -C ₆ ) alkoxy group, (vi) halo (C ₁ -C ₆ ) alkoxy group, (vii) (C ₁ -C ₆ ) alkylthio group, (viii) halo (C ₁ -C ₆ ) A substituted phenylamino-carbonyl group having, on the ring, one or more substituents selected from an alkylthio group and (ix) (C ₁ -C ₆ ) alkoxycarbonyl group;
(37e) _(C 1 -C ₆₎ alkoxyimino _(C 1 -C ₆₎ alkyl group;
(38e) phenyl _(C 1 -C ₆₎ alkoxyimino _(C 1 -C ₆₎ alkyl group; or
(39e) may be the same or different and (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, v) (C ₁ -C ₆ ) alkoxy group, (vi) halo (C ₁ -C ₆ ) alkoxy group, (vii) (C ₁ -C ₆ ) alkylthio group, (viii) halo (C ₁ -C ₆ ) alkylthio group, and _{(ix) (C} 1 -C ₆₎ alkoxy substituted phenyl having one or more substituents selected from a carbonyl group on the ring _(C 1 -C ₆₎ alkoxyimino _(C 1 -C ₆₎ alkyl Group,

More preferably,
(4e) a (C ₁ -C ₆ ) alkyl group;
(5e) a halo (C ₁ -C ₆ ) alkyl group;
(7e) a (C ₁ -C ₆ ) alkoxy group;
(8e) a halo (C ₁ -C ₆ ) alkoxy group;
(10e) a (C ₁ -C ₆ ) alkylthio group;
(11e) a halo (C ₁ -C ₆ ) alkylthio group;
(12e) a (C ₁ -C ₆ ) alkylsulfinyl group;
(13e) a halo (C ₁ -C ₆ ) alkylsulfinyl group;
_{(14e) (C 1 -C 6} ) alkylsulfonyl group;
(15e) a halo (C ₁ -C ₆ ) alkylsulfonyl group;
(22e) a phenyl group;
(23e) may be the same or different, (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, ( v) a substituted phenyl group having one or more substituents selected from (C ₁ -C ₆ ) alkoxy groups and (vi) halo (C ₁ -C ₆ ) alkoxy groups; or
(28e) a (C ₁ -C ₆ ) alkoxycarbonyl group,

Particularly preferably,
(4e) a (C ₁ -C ₆ ) alkyl group;
(5e) a halo (C ₁ -C ₆ ) alkyl group;
(23e) may be the same or different, (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, ( v) a substituted phenyl group having one or more substituents selected from (C ₁ -C ₆ ) alkoxy groups and (vi) halo (C ₁ -C ₆ ) alkoxy groups; or
(28e) a (C ₁ -C ₆ ) alkoxycarbonyl group.

The N-2- (substituted pyrazolyl) ethylcarboxamide derivative represented by the general formula (I) of the present invention is produced, for example, according to the following production method, but is not limited thereto.
Manufacturing method 1

(In the formula, Ar, R ¹ , R ² , R ³ , X, Y ¹ , Y ² , Y ³ and n are the same as above.)
Reaction of (hetero) cyclic carboxylic acid represented by general formula (II-1) with 2- (substituted pyrazolyl) ethylamine represented by general formula (III) in the presence of a condensing agent, a base and an inert solvent Thus, the N-2- (substituted pyrazolyl) ethyl carboxamide derivative of the present invention represented by the general formula (I) can be produced.

  Examples of the condensing agent used in this reaction include diethyl cyanophosphate (DEPC), carbonyldiimidazole (CDI), 1,3-dicyclohexylcarbodiimide (DCC), chlorocarbonates, 2-chloro-1-methylpyridinium iodide. Etc., and the amount used is appropriately selected from the range of 0.8 to 1.5 moles relative to the (hetero) cyclic carboxylic acid represented by the general formula (II-1). And use it.

  Examples of the base include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate and potassium hydrogen carbonate; acetates such as sodium acetate and potassium acetate; potassium tert-butoxide, sodium Alkali metal alkoxides such as methoxide and sodium ethoxide; tertiary amines such as triethylamine, diisopropylethylamine and 1,8-diazabicyclo [5.4.0] undec-7-ene; pyridine, dimethylaminopyridine and the like A nitrogen-containing aromatic compound etc. can be mentioned, The usage-amount is in the range of 0.5 times mole-10 times mole normally with respect to the (hetero) cyclic carboxylic acid represented by general formula (II-1). used.

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; halogens such as methylene chloride, chloroform and carbon tetrachloride. Halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; Chain or cyclic ethers such as diethyl ether, dioxane and tetrahydrofuran; Esters such as ethyl acetate; Amides such as dimethylformamide and dimethylacetamide Ketones such as acetone and methylethyl; inert solvents such as dimethyl sulfoxide and 1,3-dimethyl-2-imidazolidinone can be exemplified, and these inert solvents can be used alone or in combination of two or more. Can be used.
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. 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 48 hours.
After completion of the reaction, it may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.
Manufacturing method 2

(In the formula, Ar, R ¹ , R ² , R ³ , X, Y ¹ , Y ² , Y ³ and n are the same as described above, and hal represents a halogen atom.)
The (hetero) cyclic carboxylic acid halide represented by the general formula (II-2) is reacted with 2- (substituted pyrazolyl) ethylamine represented by the general formula (III) in the presence of a base and an inert solvent. Thus, the N-2- (substituted pyrazolyl) ethyl carboxamide derivative of the present invention represented by the general formula (I) can be produced.

  Examples of the base used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate; acetates such as sodium acetate and potassium acetate; alkali metal alkoxides such as t-butoxide, sodium methoxide, sodium ethoxide; tertiary amines such as triethylamine, diisopropylethylamine, 1,8-diazabicyclo [5.4.0] undec-7-ene; pyridine, Nitrogen-containing aromatic compounds such as dimethylaminopyridine and the like can be mentioned, and the amount used is usually 0.5-fold mol with respect to the (hetero) cyclic carboxylic acid halide represented by the general formula (II-2). It is used in the range of 10 times mole.

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; halogens such as methylene chloride, chloroform and carbon tetrachloride. Halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; Chain or cyclic ethers such as diethyl ether, dioxane and tetrahydrofuran; Esters such as ethyl acetate; Amides such as dimethylformamide and dimethylacetamide Ketones such as acetone and methylethyl; inert solvents such as dimethyl sulfoxide and 1,3-dimethyl-2-imidazolidinone can be exemplified, and these inert solvents can be used alone or in combination of two or more. Can be used.
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. 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 48 hours.
After completion of the reaction, it may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.
Manufacturing method 3

(In the formula, Ar, R ¹ , R ² , R ³ , X, n, Y ¹ , Y ² , Y ³ and hal are the same as described above. Boc represents a t-butoxycarbonyl group.)
By reacting the (hetero) cyclic carboxylic acid halide represented by the general formula (II-2) with the ethanolamine represented by the general formula (IV) in an inert solvent in the presence of a base, Aldehyde represented by the general formula (VI) by oxidizing the hydroxyl group in the presence of an inert solvent with or without isolating the amide derivative (V) as an amide derivative represented by the formula (V) By reacting t-butylcarbazate represented by the formula (VII) with or without the isolation of the aldehyde derivative (VI) in the presence of an inert solvent as a derivative, in the general formula (VIII) A carbazine represented by the general formula (IX) by reducing the carbon-nitrogen double bond in the presence of an inert solvent with or without isolation of the hydrazone derivative (VIII) An acid derivative, A hydrazine derivative represented by the general formula (X) is obtained by deprotecting the t-butoxycarbonyl group in the presence of an inert solvent with or without isolating the rubazine acid derivative (IX). N) of the present invention represented by the general formula (I-1) is obtained by reacting the diketone represented by the general formula (XI) with or without being isolated in the presence of an inert solvent. 2- (Substituted pyrazolyl) ethyl carboxamide derivatives can be prepared.

3-1) General formula (II-2) → General formula (V)
This reaction may be performed in the same manner as in production method 2.

3-2) General formula (V) → General formula (VI)
Examples of the oxidizing agent that can be used in this reaction include manganese dioxide, chromic acid, ceric ammonium nitrate (CAN), silver carbonate, pyridine-sulfuric anhydride, activated DMSO (dimethyl sulfoxide), and the like. Known literature used for the conversion of alcohol to aldehyde or ketone (for example, edited by The Chemical Society of Japan, “New Experimental Chemistry Course”, Volume 15 (I), p. 71-84, 120-123, 804-843, 923, 1004-1006, 1977, see Maruzen Co., Ltd. and Chem. Pharm. Bull., 30 (5), p 1921-1924 (1982).).

3-3) General formula (VI) → General formula (VIII)
This reaction may be carried out according to the method described in known literature (for example, J. Org. Chem., 46 , p 5413-5414 (see 1981). As an inert solvent, the progress of this reaction is not significantly inhibited. For example, alcohols such as methanol, ethanol, propanol and butanol; aromatic hydrocarbons such as benzene, toluene and xylene; halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride; chlorobenzene, Halogenated aromatic hydrocarbons such as dichlorobenzene; linear or cyclic ethers such as diethyl ether, dioxane and tetrahydrofuran; esters such as ethyl acetate; amides such as dimethylformamide and dimethylacetamide; 1,3-dimethyl- Illustrate inert solvents such as 2-imidazolidinone Bets can be, these inert solvents may be used singly or as mixtures 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. 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 48 hours. For the purpose of accelerating the reaction, a catalytic amount of acid such as formic acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid, hydrochloric acid, sulfuric acid and the like can be added.
After completion of the reaction, it may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.

3-4) General formula (VIII) → General formula (IX)
As the reducing agent that can be used in this reaction, diborane, borane-THF (tetrahydrofuran) complex, borane-dioxane complex, lithium borohydride, sodium borohydride, lithium aluminum hydride, hydrogen-metal catalyst (catalytic hydrogenation; metal Examples of the catalyst include Raney nickel, palladium, platinum, rhodium, etc.), but publicly known literature (for example, edited by the Chemical Society of Japan, “New” The method described in “Experimental Chemistry Course”, Volume 15 (II), p.165, 198, 333, 1977, Maruzen Co., Ltd.) may be used.

3-5) General formula (IX) → General formula (X)
This reaction may be performed according to a method described in known literature (for example, see J. Org. Chem., 43 , p2285 (1978)) used for deprotection of the Boc group (t-butoxycarbonyl group). The hydrazine derivative represented by the general formula (X) is isolated as an inorganic acid salt such as hydrochloride, sulfate or nitrate, or as an organic acid salt such as formate, acetate, trifluoroacetate or methanesulfonate. It can also be used for the next reaction.

3-6) General formula (X) → General formula (XI)
The inert solvent that can be used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction. For example, alcohols such as methanol, ethanol, propanol, and butanol; aromatic hydrocarbons such as benzene, toluene, and xylene Halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; linear or cyclic ethers such as diethyl ether, dioxane and tetrahydrofuran; ethyl acetate and the like; Esters; Amides such as dimethylformamide and dimethylacetamide; Inert solvents such as 1,3-dimethyl-2-imidazolidinone can be exemplified, and these inert solvents can be used alone or in combination of two or more. Can be used.
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. 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 48 hours. For the purpose of accelerating the reaction, a catalytic amount of acid such as formic acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid, hydrochloric acid, sulfuric acid and the like can be added.
After completion of the reaction, it may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.

The 2- (substituted pyrazolyl) ethylamine represented by the general formula (III) which is an intermediate of the present invention can be produced, for example, according to the following intermediate production methods 1 to 3.
Intermediate production method 1

(In the formula, R ¹ , R ² , R ³ , Y ¹ , Y ² , Y ³ and Boc are the same as above.)
2- (Substituted pyrazolyl) ethyl represented by general formula (III-1) is obtained by Mitsunobu reaction of ethanolamines represented by general formula (IV-1) and pyrazoles represented by general formula (XII). 2- (Substitution represented by the general formula (III), which is an intermediate of the present invention, by carbamates and by deprotecting the Boc group with or without isolating the carbamates (III-1) Pyrazolyl) ethylamine can be prepared.
1-a) General formula (IV-1) → General formula (III-1)
This reaction may be performed according to a method described in known literature (for example, see Bull. Chem. Soc. Jpn., 40 , p2380-2382 (1967)).
1-b) General formula (III-1) → General formula (III)
This reaction may be carried out in the same manner as 3-5).
Intermediate production method 2

(Wherein R ¹ , R ² , R ³ , Y ¹ , Y ² , Y ³ and Boc are the same as above. L represents a leaving group such as a halogen atom, a methanesulfonyloxy group, a p-toluenesulfonyloxy group, etc. Show.)
The amine represented by the general formula (IV-2) and the pyrazole represented by the general formula (XII) are reacted in the presence of a base and an inert solvent and represented by the general formula (III-1). 2- (Substituted pyrazolyl) ethyl carbamates, and the Boc group is deprotected with or without isolation of the carbamates (III-1), whereby the intermediate of the present invention is represented by the general formula (III) The represented 2- (substituted pyrazolyl) ethylamine can be prepared.
2-a) General formula (IV-2) → General formula (III-1)
This reaction may be carried out according to production method 2.
2-b) General formula (III-1) → General formula (III)
This reaction may be carried out in the same manner as 3-5).
Intermediate production method 3

(In the formula, R ¹ , Y ¹ , Y ² , Y ³ and hal are the same as above. Me represents a methyl group.)
A haloketone represented by the general formula (XIII) and a pyrazole represented by the general formula (XII) are reacted in the presence of a base and an inert solvent to obtain a pyrazolyl ketone represented by the general formula (XIV). The pyrazolyl ketones (XIV) are isolated or not isolated, and reacted with methoxyamine in the presence of an inert solvent to obtain oximes represented by the general formula (XV), and the oximes are isolated. Alternatively, 2- (substituted pyrazolyl) ethylamine represented by the general formula (III-2) can be produced by reduction in the presence of an inert solvent without isolation.
3-a) General formula (XIII) → General formula (XIV))
This reaction may be carried out according to production method 2.
3-b) General formula (XIV) → General formula (XV)
This reaction may be carried out in the same manner as in 3-3).
3-c) General formula (XV) → General formula (III-2)
This reaction may be carried out in the same manner as 3-4).

Representative examples of N-2- (substituted pyrazolyl) ethylcarboxamide derivatives represented by the general formula (I) of the present invention are shown in Tables 1 to 5, and each intermediate is shown in Tables 6 to 10. However, the present invention is not limited to these.
In Tables 1 to 10, “Me” represents a methyl group, “Et” represents an ethyl group, “Pr” represents a propyl group, “Bu” represents a butyl group, “Ph” represents a phenyl group, “ “Py” represents a pyridyl group, “n-” represents normal, and “i-” represents iso.
The physical properties indicate melting point (° C.) or refractive index n _D (measurement temperature ° C.).
A1 to A26 show the following structures.
Among the compounds of the present invention represented in Tables 1 to 10, when an asymmetric carbon is present, the absolute configuration is the (S) isomer, but a compound numbered with “*” Is a racemate, and Compound No. I-11 is an (R) isomer.
The “bonding position” in Table 4 indicates the bonding position (3-position or 5-position) of the benzene ring to the pyrazole ring, and the compound described as “Mixture” is a mixture of the 3-position and 5-position. Indicates.
“Mixture” in the remarks column in Table 8 indicates a mixture of Y ¹ and a compound in which Y ³ is exchanged.
Incidentally, the compound described as "Amorphous" or "Paste" the physical value column of Table 1 to Table 5, the compounds described as "NMR" physical property value column of the sixth to tenth Table, Part ¹ HNMR The spectral data are shown in Table 11. In Table 11, s is a single line, d is a double line, t is a triple line, q is a quadruple line, quintet is a quintet line, dd is a double double line, and m is a multiple line.
In addition, in the NMR spectrum data of the mixture, for example, when two singlets belonging to the respective compounds are observed at chemical shifts of 2.89 ppm and 2.88 ppm, indicating a total of three hydrogen integrals, “2.89, 2.88 (s , 3H) ”.

The pest control agent containing the N-2- (substituted pyrazolyl) ethylcarboxamide derivative represented by the general formula (I) of the present invention or a salt thereof as an active ingredient is particularly used for rice, fruit trees, vegetables, other crops and flowers. Suitable for controlling plant diseases and nematodes in soil.
The target diseases for use of the plant disease control agent of the present invention are filamentous fungal diseases, bacterial diseases, and viral disease diseases, for example, diseases caused by imperfect fungi (for example, diseases of the genus Botrytis, Helminthosporia) Genus diseases, Fusarium genus diseases, Septoria genus diseases, Sarcospora genus diseases, Pseudocercosporella genus diseases, Linchosporium genus Pulicia diseases, Pyricularia disease Alternaria disease, etc.), basidiomycetes (eg, Hemelia disease, Rhizoctonia genus) Harmful diseases, diseases of the genus Ustilago, diseases of the genus Typhula, diseases of the genus Puccinia, diseases of the Ascomycota fungi (for example, diseases of the genus Venturia, diseases of the genus Podospherea, Leptopha Diseases of the genus Leptosphaeria, diseases of the genus Blumeria, diseases of the genus Erysiphe, diseases of the genus Microdocium, diseases of the genus Sclerotinia, diseases of the genus Gemanionis , Diseases of the genus Unsinula, etc.) and other fungi (for example, the genus Ascochita) Harm, genus Phoma, disease of genus Pythium, disease of genus Corticium, disease of genus Pyrenophora, etc., diseases caused by bacteria, for example, diseases of the genus Pseudomonas, Zantomonas (Xanthomonas) diseases, Erwinia diseases, etc., or diseases caused by viruses (for example, tobacco mosaic virus) can be mentioned.

  Specific diseases include, for example, rice blast disease (Piculararia oryzae), rice sheath blight (Rhizotonia suraminus), rice sesame leaf blight (Cochiobulus mirabeumususi), rice seedling blight (Rhizopus minusumisumusisumususi) roseum, Mucor sp., Puma sp., Tricoderma sp.), rice idiot seedlings (Gibberella fujikuroi), powdery mildew (Blumeria graminis) such as barley and wheat, or cucumbers such as cu Powdery mildew such as ( rysiphe cichoacoarum) and other host plants powdery mildew, barley and wheat and other eye spot diseases (Pseudocercosporella herpotrichoides), wheat and other scab (Urocystis tritici), barley and wheat, etc. , Typhla ishikariensis, Typhla incarnata, Sclerotinia borealis, barley and wheat, etc. Fusarium gramineumum, Fusarium avenumum, Fusarium umariaumum, Fusarium umariaumum, Fusarium umariaumum Wheat and other rust diseases (Puccinia recondita, Puccinia striformis, Puccinia graminis), barley and wheat and other leaf blight (Gaeumanomyces graminis), oat crown rust (Puccinia crust and other diseases) Gray mold disease (Botrytis cinerea), sclerotia of tomato, cabbage, etc. (Sclerotinia sclerotiorum), potato, tomato, etc. Species such as downy mildew (Plasmopara viticola) Plant downy mildew, apple black spot disease (Venturia inaequalis), apple spotted leaf disease (Alternaria mali), pear black spot disease (Alternaria kikuchiana), citrus black spot disease (Diaporthe citri), citrus sock disease Sugar beet brown spot (Cercospora beticola), peanut brown spot (Cercospora arachidicola), peanut black astringency (Cercospora personata), wheat leaf blight (Septoria tritici), wheat leaf blight (o morp disease) Pyrenophora teres), barley leaf spot (Pyrenop) hora graminea, barley cloud scab (Rhynchosporium secalis), wheat bare smut (Ustilago anua), wheat scab (Tillletia caries), leaf rot (Rhizoctonia sola) According to the genus Psuedomonas, for example, Pseudomonas syringae pv. lachrymans), tomato bacterial wilt (Pseudomonas solanacearum), rice bacterial wilt (Pseudomonas glumae), Xanthomonas genus, such as cabbage black rot (Xanthomonas campstris), X citri), bacterial diseases such as cabbage soft rot (Erwinia carotovora), viral diseases such as tobacco mosaic disease (Tobacco mosaic virus), etc. due to the genus Erwinia.

  Also, as nematodes, Pratylenchus coffeae, potato cyst nematode (Glabodera rosteniens nematode), Meloidogyne pneum senne (Melodigine selenium nematode) avenae), Agalenchoides ritzemabosi and the like.

  Plants that can use the pest control agent of the present invention, in particular plant disease control agent or nematicide, are not particularly limited, for example, cereals (for example, rice, barley, wheat, rye, oats, corn, Takatsuki, etc.), beans (soybeans, red beans, broad beans, peas, peanuts, etc.), fruit trees and fruits (apples, citrus fruits, pears, grapes, peaches, plums, cherry peaches, walnuts, almonds, bananas, strawberries, etc.), vegetables (Cabbage, tomato, spinach, broccoli, lettuce, onion, leek, pepper, etc.), root vegetables (carrot, potato, sweet potato, radish, lotus root, turnip, etc.) Rapeseed, beet, hop, sugar cane, sugar beet, olive, rubber, coffee, tobacco, tea, etc.), moss (pumpkin, cucumber, watermelon, melon, etc.), grass (Orchardgrass, sorghum, timothy, clover, alfalfa, etc.), turf (Korean turf, bentgrass, etc.), fragrance crops (lavender, rosemary, thyme, parsley, pepper, ginger, etc.), flowers (chrysanthemum, chrysanthemum, Rose, orchid, etc.).

  In recent years, genetically modified crops (herbicide-tolerant crops, pest-resistant crops incorporating insecticidal protein-producing genes, disease-resistant crops incorporating resistance-inducing substance-producing genes for diseases, food-enhancing crops, preservative-enhancing crops, yield Improved crops, etc.), insect pheromones (communications of oyster moths, mushrooms, etc.), IPM (total pest management) technology using natural enemy insects, etc., and the pest control agent of the present invention, especially Plant disease control agents or nematicides can be used in combination with these techniques or systematized.

When the compound of the present invention is used as an active ingredient of a pest control agent, it may be used as it is without adding other components. However, it is usually used after being formulated into a convenient shape according to a conventional method on an agrochemical formulation. Is common.
That is, the N-2- (substituted pyrazolyl) ethylcarboxamide derivative represented by the general formula (I) or a salt thereof is blended in an appropriate ratio together with an appropriate inert carrier or an auxiliary agent as necessary. And dissolved, separated, suspended, mixed, impregnated, adsorbed or adhered to an appropriate dosage form, such as a suspension, emulsion, liquid, wettable powder, wettable powder, granule, powder, tablet, pack. It is used as a formulation.

  The inert carrier that can be used in the present invention may be either solid or liquid. Examples of materials that can be used as the solid carrier include soybean flour, cereal flour, wood flour, bark flour, saw flour, and tobacco stem. Powder, walnut shell powder, bran, fiber powder, residue after extraction of plant extract, synthetic polymer such as pulverized synthetic resin, clay (eg kaolin, bentonite, acid clay), talc (eg talc, pyrophyllite, etc.) ), Silica {e.g., diatomaceous earth, silica sand, mica, white carbon (some synthetic high-dispersion silicic acid, also called hydrous finely divided silicon, hydrous silicic acid, and some products contain calcium silicate as a main component)}, activated carbon, sulfur powder, Pumice, calcined diatomaceous earth, brick ground, fly ash, sand, calcium carbonate, calcium phosphate and other inorganic mineral powders, polyethylene, polypropylene, poly Plastic carriers, ammonium sulfate, ammonium phosphate, such as fluoride, ammonium nitrate, urea, fertilizer salts depreciation etc., can be exemplified compost or the like, which are used alone or in the form of a mixture of two or more.

  The material that can be used as a liquid carrier is selected from those having solvent ability itself and those capable of dispersing the active ingredient compound with the aid of an auxiliary agent without having solvent ability. The following carriers can be exemplified, but these are used singly or in the form of a mixture of two or more. For example, water, alcohols (for example, methanol, ethanol, isopropanol, butanol, ethylene glycol, etc.), ketones ( For example, 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, etc.) , Aromatic hydrocarbons (eg, ben , Toluene, xylene, solvent naphtha, alkylnaphthalene, etc.), halogenated hydrocarbons (eg, dichloroethane, chloroform, carbon tetrachloride, chlorinated benzene, etc.), esters (eg, ethyl acetate, diisopropyl phthalate, dibutyl phthalate, Dioctyl phthalate, etc.), amides (eg, dimethylformamide, diethylformamide, dimethylacetamide, etc.), nitriles (eg, acetonitrile, etc.), dimethyl sulfoxides, and the like.

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 together. In some cases, no adjuvant may be used.
Surfactants are used for the purpose of emulsifying, dispersing, solubilizing and / or wetting the active ingredient compound, for example, polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene higher fatty acid ester, polyoxyethylene List surfactants such as ethylene resin acid ester, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, alkylaryl sulfonate, naphthalene sulfonate condensate, lignin sulfonate, higher alcohol sulfate Can do.
Further, for the purpose of stabilizing the dispersion of the active ingredient compound, sticking and / or binding, the following auxiliary agents can be used, for example, casein, gelatin, starch, methylcellulose, carboxymethylcellulose, gum arabic, Adjuvants such as polyvinyl alcohol, pine oil, coconut oil, bentonite and lignin sulfonate can also be used.

  In order to improve the fluidity of the solid product, the following adjuvants may be used, and for example, adjuvants such as waxes, stearates and alkyl phosphates may be used. As a peptizer for the suspension product, for example, auxiliary agents such as naphthalenesulfonic acid condensate and condensed phosphate can be used. As the antifoaming agent, for example, an auxiliary agent such as silicone oil can be used. As a preservative, 1,2-benzisothiazolin-3-one, parachlorometaxylenol, butyl paraoxybenzoate, 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 (dibutylhydroxytoluene), UV absorption, as necessary Other additives such as an agent can also be added.

  The blending ratio of the active ingredient compound can be adjusted as necessary, and it may be appropriately selected from the range of 0.01 to 90 parts by weight in 100 parts by weight of the pest control agent. When it is used as a powder, powder or granule, 0.01 to 50% by weight is appropriate. The pest control agent of the present invention may be used as it is, or appropriately diluted with water or suspended in order to control various diseases or nematodes. The amount of use of the pest control agent of the present invention depends on various factors such as purpose, target disease, crop growth, disease 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 from the range of 0.001 g to 10 kg, preferably 0.01 g to 1 kg per 10 are according to the purpose.

  Pest control agents used in the method of the present invention, particularly plant disease control agents or nematicides, are used as they are, or appropriately diluted with water or suspended in order to control various diseases or nematodes. The amount effective for pest control can be used by applying the usual method to the seed of the target plant for which the occurrence of the pest is predicted or the cultivation carrier for sowing, etc. Can be used in application methods such as clothing, seed disinfection method, planting hole treatment, plant root treatment, rowing treatment, soil mixing, etc., for diseases that occur in field crops such as fruit trees, cereals, vegetables The seed treatment such as dressing and soaking, soaking of seedling roots, cropping at the time of sowing, cultivation containers and planting holes for raising seedlings, irrigation to raising seedling carriers such as stocks, surface spraying, mixing treatment, etc. It can be carried out by post-irrigation or the like and absorbed in plants. You may process to the hydroponic liquid in hydroponics.

As a seed treatment method, for example, a method of immersing seeds in a liquid state by diluting or not diluting a liquid or solid preparation and infiltrating the drug according to a usual method, a solid preparation or a liquid preparation is used as a seed. Method of adhering to the surface of the seed by blending, dressing treatment, etc., mixing with a highly adherent carrier such as resin, polymer, etc., coating the seed in a single layer or multiple layers, spraying around the seed simultaneously with planting And the like. The “seed” for performing the seed treatment is broadly synonymous with the “reproduction plant body” in the present invention, and in addition to so-called seeds, bulbs, tubers, seeds, bulbs, stems for cutting plant cultivation, etc. Includes plants for vegetative propagation.
“Soil” or “cultivation carrier” in the case of carrying out the method of the present invention refers to a support for cultivating a plant, and the material is not particularly limited as long as it is a material on which a plant can grow. Well, for example, it contains so-called various soils, seedling mats, water, etc., sand, vermiculite, cotton, paper, diatomaceous earth, agar, gel material, polymer material, rock wool, glass wool, wood chip, bark, pumice Etc. can also be included.

  Examples of application methods to the soil include, for example, a method in which a liquid or solid preparation is diluted or not diluted with water and applied to the vicinity of a plant installation place or a nursery bed for raising seedlings, etc. The method of spraying in the vicinity or nursery, the method of spraying powder, wettable powder, wettable granule powder, granule etc. before sowing or transplanting and mixing with the whole soil, the planting hole before sowing or before planting the plant, Examples include a method of spraying powder, wettable powder, wettable powder, granule, etc. on the strip.

  As a method for applying paddy rice to a seedling box, the dosage form may vary depending on the time of application such as application at seeding, application at greening period, application at transplantation, etc., but agents such as powder, granule wettable powder, granules, etc. Apply with a mold. It can also be applied by mixing with soil, and it can be mixed with soil and powder, granulated wettable powder or granules, for example, mixed with ground soil, mixed with soil covering, mixed with the entire soil. Simply, the soil and various preparations may be applied alternately in layers. The time of application at the time of sowing may be before sowing, at the same time, after sowing, or after soil covering.

In field crops such as wheat, treatment from a seed or a cultivating carrier in the vicinity of the plant body is preferable from the sowing to the seedling raising period. In plants that are sown directly in a field, in addition to direct treatment on seeds, treatment on a cultivation carrier or the like adjacent to the plant being cultivated is suitable. It is possible to perform spraying treatment using a granule or irrigation treatment in a liquid of a drug diluted or not diluted in water.
As the seeding of the cultivated plant to be transplanted and the treatment of the seedling raising period, in addition to the direct treatment to the seed, the irrigation treatment of the liquid medicine or the spraying treatment of the granule can be performed on the seedling bed for raising the seedling. Moreover, a granule can also be processed to a planting hole at the time of planting, and can be mixed with the cultivation support | carrier of the transplanting site vicinity.

The pest control agents of the present invention, particularly plant disease control agents or nematicides, are further used as other fungicides, insecticides, insecticides for the purpose of controlling pests to be controlled, expansion of the appropriate period of control, or for the purpose of reducing the dose. It can also be used by mixing with acaricide, nematicide, biological pesticide, etc., and can also be used by mixing with herbicides, plant growth regulators, fertilizers, etc. depending on the situation of use.
Other fungicides used for this purpose are, for example, sulfur, lime sulfur combinations, basic copper sulfate, iprobenphos, edifenphos, tolcrofos methyl, thiram, polycarbamate, dinebu, manzeb, mancozeb, propineb, thiophanate, Thiophanate methyl, benomyl, iminotadine acetate, iminoctadine albecylate, mepronil, flutolanil, pencyclon, furamethopyl, tifluzamide, metalaxyl, oxadixyl, carpropamide, diclofluanid, fursulfanamide, chlorothalonil, crestoxime methyl, phenoxanil, himexazole Procymidone, Vinclozoline, Iprodione, Triazimephone, Vitertanol, Triflumizole, Ipconazole, Flu Nazole, propiconazole, diphenoconazole, microbutanyl, tetraconazole, hexaconazole, tebuconazole, thiazinyl, imibenconazole, prochloraz, pefrazoate, cyproconazole, isoprothiolane, phenarimol, pyrimethanil, mepanipyrim, pyrifenox, fluazinam, triphorin, Dichromedin, azoxystrobin, thiadiazine, captan, probenazole, acibenzoral S methyl, fusaride, tricyclazole, pyroxylone, quinomethionate, oxolinic acid, dithianon, kasugamycin, validamycin, polyoxin, blasticidin, streptomycin, etc.

Examples of insecticides, acaricides, and nematicides used for the same purpose include, for example, ethion, trichlorfone, methamidophos, acephate, dichlorvos, mevinphos, monocrotophos, malathion, dimethoate, formothione, mecarbam, bamidthione, thiomethone, disulfotone. , Oxydeprophos, nared, methyl parathion, fenitrothion, cyanophos, propaphos, fenthion, prothiophos, profenophos, isofenphos, temefos, phentoate, dimethylvinphos, chlorfevinphos, tetrachlorvinphos, phoxime, isoxathione, pyraclophos, methidathion, chloropyrifos , Chlorpyrifos methyl, pyridafenthione, diazinon, pyrimifosmethyl, hosalon, phosmet, dioxaben Host, quinalphos, terbufos, ethoprophos, cadusafos, Mesurufenhosu, DPS (NK-0795),

Phosphocarb, phenamiphos, isoamidophos, isothiafos, isothiafos, enaprofos, fenthion, phosthiethane, diclofenthion, thionadine, sulprophos, fencerfothion, diamidaphos, pyrethrin, allethrin, plaretrin, resmethrin, permethrin, bifluthrin, profenthrin, profenthrin, profenthrin, profenthrin Cypermethrin, cyhalothrin, lambda cyhalothrin, deltamethrin, acrinatrin, fenvalerate, esfenvalerate, cycloprotorin, etofenprox, halfenprox, silafluophene, flucitrinate, fulvalinate, mesomil, oxamyl, thiodicarb, aldicarb, Alanicarb, Cartap, Metorcarb, Kishi Carb, propoxyl, phenoxycarb, fenobucarb, etiophencarb, phenothiocarb, bifenazate, BPMC (2-secondarybutylphenyl-N-methylcarbamate), carbaryl, pirimicurve, carbofuran, carbosulfan, furthiocarb, benfuracarb, aldoxycarb, diafenthiu Ron, diflubenzuron, teflubenzuron, hexaflumuron, novallon, lufenuron, flufenoxuron, chlorfluazuron, fenbutane oxide, tricyclohexyltin hydroxide, sodium oleate, potassium oleate, methoprene, hydroprene, binapacryl, amitraz, dicophor , Kelsen, chlorbenzilate, phenisobromolate, tetradiphone, bensultap, Zomate, tebufenozide, methoxyphenozide, pyridalyl, metaflumizone, fulvendiamide, chromafenozide, propargite, acequinosyl, endosulfan, diophenolane, chlorfenapyr, fenpyroximate, tolfenpyrad, fipronil, tebufenpyrad, triazamate, ethoxazole, prixamthram Thiamethoxam, clothianidin, dinotefuran, fluazinam, pyriproxyfen, hydramethylnon, pyrimidifen, pyridaben, cyromazine, TPIC (tripropylisocyanurate), pymetrozine, clofentezine, buprofezin, thiocyclam, phenazaquin, quinomethionate Indoxacarb, polynactin complex, milbemectin, abamectin, emamectin benzoate, spinosad, BT (Bacillus thuringiensis), azadilactin, rotenone, hydroxypropyl starch, levamisole hydrochloride, metam sodium, morantel tartrate, dazomet, trichramide, Bastoria, Monacrosporium, Fimatopagum, etc.

Similarly, herbicides include, for example, glyphosate, sulfosate, glufosinate, bialaphos, butamifos, esprocarb, prosulfocarb, beniocarb, pyribuchicarb, ashram, linuron, diimron, isouron, bensulfuron methyl, cyclosulfamuron, sinosulflon, pyrazos Ruflon ethyl, azimusulfuron, imazosulfuron, tenylchlor, alachlor, pretilachlor, clomeprop, etobenzanide, mefenacet, pendimethalin, bifenox, acifluophene, lactofen, cihalohop butyl, ioxynyl, bromobutide, aroxidim, cetoxidim, napropamide, napropamide, Pyrazolate, benzophenap, pyraflufenethyl, imazapyr Sulfentrazone can cafenstrole, Bentokisazon, oxadiazon, paraquat, diquat, pyriminobac, simazine, atrazine, dimethametryn, triaziflam, benfuresate, fluthiacet-methyl, quizalofop-ethyl, be mentioned bentazone, the calcium peroxide and the like.

Next, the present invention will be specifically described with reference to examples. However, the present invention is not limited to these examples as long as the gist of the invention is not exceeded.
Example 1.2 Preparation of [3,5-bis (trifluoromethyl) pyrazol-1-yl] -1-methylethylamine (Compound No. VIII-9) Triphenylphosphine (5.51 g, 21 mmol) was added to tetrahydrofuran ( 30 ml), and tertiary butyl (2-hydroxy-1-methylethyl) carbamate (2.63 g, 15 mmol) and 3,5-bis (trifluoromethyl) -1H-pyrazole (3.06 g, 15 mmol) Were dissolved successively, and diethyl azodicarboxylate (40% toluene solution, 9.8 g, 22.5 mmol) was added dropwise under ice-water cooling. After returning to room temperature, the mixture was stirred for 2 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography. The obtained organic substance was mixed with 30 ml of 4N hydrochloric acid / ethyl acetate solution and stirred for 1 hour. The target product is extracted from the reaction mixture with water, and the resulting aqueous layer is made basic by adding potassium carbonate. The target product is extracted with ethyl acetate, the extract is washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. This gave the target product (2.3 g) (yield 59%).
Physical properties: ¹ H-NMR [CDCl ₃ / TMS, δ value (ppm)]
6.90 (s, 1H), 4.24-4.06 (m, 2H), 3.62-3.53 (m, 1H), 1.68 (br, 2H), 1.17 (d, 3H)

Example 2 Preparation of N- {2- [3,5-bis (trifluoromethyl) pyrazol-1-yl] -1-methylethyl} -2-iodobenzamide (Compound No. I-10) 2- [3,5-Bis (Trifluoromethyl) pyrazol-1-yl] -1-methylethylamine (0.26 g, 1 mmol) was mixed with tetrahydrofuran (10 ml), triethylamine (0.30 g, 3 mmol), 2-iodobenzoic acid (0. 25 g, 1 mmol) and 2-chloro-1-methylpyridinium iodide (0.31 g, 1.2 mmol) were sequentially added and stirred for 2 hours. Water was added to the reaction mixture, and the target product was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain the desired product (0.39 g) (yield 79%).
Physical property: Melting point 114-115 ° C

Example 3 Preparation of N- {2- [3,5-bis (trifluoromethyl) pyrazol-1-yl] -1-methylethyl} -2-trifluoromethylbenzamide (Compound No. I-15) 2- [3,5 -Bis (trifluoromethyl) pyrazol-1-yl] -1-methylethylamine (0.20 g, 0.76 mmol) was mixed with tetrahydrofuran (10 ml), and further triethylamine (0.08 g, 1.1 mmol), 2- Trifluoromethylbenzoyl chloride (0.16 g, 0.76 mmol) was sequentially added and stirred for 2 hours. Water was added to the reaction mixture, and the target product was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain the desired product (0.21 g) (yield 64%).
Physical property: Melting point 81-82 ° C

Production Example 1.1 Production of 1- [4- (2-chlorophenyl) pyrazol-1-yl] propan-2-one (Compound No. IX-2) 4- (2-Chlorophenyl) -1H-pyrazole (1.08 g, 6.0 mmol) is dissolved in acetone (10 ml) and further chloroacetone (0.83 g, 9.0 mmol), potassium carbonate (1.0 g, 7.2 mmol) and potassium iodide (0.1 g, 0.6 mmol). Were sequentially added and stirred for 8 hours under reflux. After allowing to cool, the salt was removed by natural filtration, and the filtrate was concentrated under reduced pressure to obtain the desired product (yield: quantitative).
Physical properties: ¹ H-NMR [CDCl ₃ / TMS, δ value (ppm)]
7.88 (s, 2H), 7.50-7.18 (m, 4H), 4.96 (s, 2H), 2.17 (s, 3H)

Production Example 2.1 Production of 1- [4- (2-chlorophenyl) pyrazol-1-yl] propan-2-one-O-methyloxime (Compound No. X-2) -1-yl] propan-2-one (1.41 g, 6.0 mmol) was mixed with ethanol (20 ml) and further triethylamine (0.97 g, 9.6 mmol) and O-methylhydroxylamine hydrochloride (0. (75 g, 9.0 mmol) was sequentially added, and the mixture was stirred for 3 hours with heating under reflux. Water was added to the residue obtained by concentrating the reaction mixture under reduced pressure, and the target product was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain the desired product (1.45 g) (yield 91%).
Physical properties: ¹ H-NMR [CDCl ₃ / TMS, δ value (ppm)]
7.86-7.83 (m, 2H), 7.48-7.17 (m, 4H), 5.10,4.83 (s, 2H), 3.92, 3.91 (s, 3H), 1.81, 1.72 (s, 3H)

Example 4. Production of 2- [4- (2-chlorophenyl) pyrazol-1-yl] -1-methylethylamine (Compound No. VIII-3) RaneyNi (1.0 g) was placed in a pressure-resistant vessel for hydrogenation. 1- [4- (2-Chlorophenyl) pyrazol-1-yl] propan-2-one-O-methyloxime (1.45 g, 5.48 mmol) and 28% aqueous ammonia (1 ml) dissolved in ethanol (20 ml) Were sequentially added, and the mixture was stirred at 4 atm for 15 hours using a hydrogenation apparatus. RaneyNi was filtered, and the filtrate was concentrated under reduced pressure. Ethyl acetate was added to the resulting residue, the target product was extracted with 10% aqueous hydrochloric acid, and the aqueous layer was washed with ethyl acetate. The aqueous layer is made basic by adding potassium carbonate, and the target product is extracted with ethyl acetate. The extract is washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain the target product (0.86 g). (Yield 66%).
Physical properties: ¹ H-NMR [CDCl ₃ / TMS, δ value (ppm)]
7.88 (s, 1H), 7.84 (s, 1H), 7.48-7.16 (m, 4H), 4.18-3.90 (m, 2H), 3.53-3.45 (m, 1H), 1.16 (d, 3H)

Production Example 3 Preparation of (S) -N- (2-hydroxy-1-methylethyl) -2-iodobenzamide (S) -2-Amino-1-propanol (3.76 g, 50 mmol) and triethylamine (25.3 g, 250 mmol) Was mixed with tetrahydrofuran (50 ml), and 2-iodobenzoyl chloride (29.3 g, 110 mmol) was added dropwise under cooling with ice water, and the mixture was returned to room temperature and stirred for 6 hours. Ethanol (50 ml) was added to the residue obtained by concentrating the reaction mixture under reduced pressure, and 3N aqueous potassium hydroxide solution (30 ml) was added dropwise with heating under reflux, followed by stirring for 3 hours. After cooling, the reaction mixture is concentrated under reduced pressure, water is added to the resulting residue, and the target product is extracted with ethyl acetate. The extract is washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain the target product. (Yield 87%).
Physical properties: ¹ H-NMR [CDCl ₃ / TMS, δ value (ppm)]
7.85 (d, 1H), 7.12-7.36 (m, 2H), 7.12-7.07 (m, 1H), 5.97 (d, 1H), 4.33-4.23 (m, 1H), 3.84-3.64 (m, 2H), 2.50 (t, 1H), 1.31 (d, 3H)

Production Example 4 Preparation of (S) -2-iodo-N- (1-methyl-2-oxoethyl) benzamide (S) -N- (2-hydroxy-1-methylethyl) -2-iodobenzamide (7.63 g, 25 mmol) And triethylamine (7.56 g, 75 mmol) were dissolved in dimethyl sulfoxide (80 ml), and a dimethyl sulfoxide solution (20 ml) of pyridine sulfate trioxide complex (11.94 g, 75 mmol) was added dropwise under ice-water cooling, followed by stirring for 30 minutes. The reaction mixture was poured into ice water (50 ml), the target product was extracted with ethyl acetate, the extract was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain the target product (quantitative yield).
Physical properties: ¹ H-NMR [CDCl ₃ / TMS, δ value (ppm)]
9.69 (s, 1H), 8.62-7.10 (m, 5H), 4.75 (q, 1H), 1.54 (d, 3H)

Production Example 5 Production of (S) -tertiarybutyl- {N ′-[2- (2-iodobenzoylamino) propylidene] hydrazine} carboxylate (Compound No. VI-4) (S) -2-iodo-N- (1- Methyl-2-oxoethyl) benzamide (7.58 g, 25 mmol) was mixed with tetrahydrofuran (80 ml), and a tetrahydrofuran solution (20 ml) of tertiary butyl hydrazinecarboxylate (3.96 g, 30 mmol) was added dropwise with cooling with ice water, followed by heating. Stir for 3 hours under reflux. After allowing to cool, water was added to the residue obtained by concentrating the reaction mixture under reduced pressure, and the target product was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain the target product (5 2 g) was obtained (yield 50%).
Physical properties: ¹ H-NMR [CDCl ₃ / TMS, δ value (ppm)]
7.87-7.07 (m, 6H), 6.60 (d, 1H), 4.90-4.82 (m, 1H), 1.51 (s, 3H), 1.49 (s, 9H)

Production Example 6 Production of (S) -N- (2-hydrazino-1-methylethyl) -2-iodobenzamide hydrochloride (Compound No. VII-4) (S) -Tertiary butyl- {N ′-[2- (2 -Iodobenzoylamino) propylidene] hydrazine} carboxylate (5.2 g, 12.5 mmol) was suspended in tetrahydrofuran (30 ml), and borane-THF complex / THF solution (18.8 mmol) was added dropwise under cooling with ice water for 30 minutes. Stir. The residue obtained by concentrating the reaction mixture under reduced pressure was mixed with 4N hydrochloric acid / ethyl acetate solution (30 ml) and stirred for 3 hours. Crystals obtained by concentrating the reaction mixture under reduced pressure were collected by filtration to obtain the desired product (quantitative yield).
Physical properties: ¹ H-NMR [DMSO-d ₆ / TMS, δ value (ppm)]
8.41-7.15 (m, 4H), 4.02 (br, 5H), 3.05-2.90 (m, 2H), 1.19 (d, 3H)

Example 5 FIG. Production of (S) -N- {2- [3,5-bis (trifluoromethyl) pyrazol-1-yl] -1-methylethyl} -2-iodobenzamide (Compound No. I-12) (S)- N- (2-hydrazino-1-methylethyl) -2-iodobenzamide hydrochloride (0.36 g, 1.0 mmol) was suspended in ethanol (6 ml), and hexafluoroacetylacetone (0.21 g, 1) was added under ice cooling. 0.0 mmol) in ethanol (4 ml) was added dropwise and the mixture was stirred for 3 hours under reflux with heating. After allowing to cool, water was added to the residue obtained by concentrating the reaction mixture under reduced pressure, and the target product was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain the desired product (0.34 g) (yield 69%). Further, when the optical purity was measured, it showed a value of> 99% ee.
Physical property: Melting point 120-121 ° C

Although the typical formulation example and test example of this invention are shown below, this invention is not limited to these.
In the preparation examples, “parts” means “parts by weight”.

Formulation Example 1
Compound of the present invention 10 parts Xylene 70 parts N-methylpyrrolidone 10 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 10 parts The above components are uniformly mixed and dissolved to prepare an emulsion.

Formulation Example 2
Compound of the present invention 3 parts Clay powder 82 parts Diatomaceous earth powder 15 parts The above is mixed and ground uniformly to form a powder.

Formulation Example 3
Compound of the present invention 5 parts Mixed powder of bentonite and clay 90 parts lignin sulfonate 5 parts The above is uniformly mixed, kneaded with an appropriate amount of water, granulated and dried to give granules.

Formulation Example 4
Compound of the present invention 20 parts Kaolin, synthetic highly dispersed silicic acid 75 parts Polyoxyethylene nonylphenyl ether and calcium alkylbenzene sulfonate 5 parts The above is uniformly mixed and ground to obtain a wettable powder.

  Next, test examples show that the compounds of the present invention are useful as plant disease control agents. In addition, this invention compound is shown with the compound number as described in Table 1-Table 5.

Test Example 1 Test for controlling apple scab disease An emulsion of the compound of the present invention prepared according to Formulation Example 1 was diluted with water to a predetermined amount and sprayed with foliage on apple seedlings (variety: Wang Lin) grown in a pot. On the next day of spraying, a spore suspension of Venturia inaequalis obtained by culturing in a PSA medium was spray-inoculated and maintained under humid conditions at 20 ° C. The control value was calculated | required according to Numerical formula 1 14 days after inoculation, and the control effect was determined according to the following reference | standard.

Judgment criteria 0: Control value 9% or less 1: Control value 10-19%
2: Control value 20-29%
3: Control value 30-39%
4: Control value 40-49%
5: Control value 50-59%
6: Control value 60-69%
7: Control value 70-79%
8: Control value 80-89%
9: Control value 90-99%
10: Control value 100%

  As a result of the above test, the compound of the present invention showed an excellent control effect at an active ingredient concentration of 200 ppm and a spray chemical amount of 50 mL. I-1, I-8, I-9, I-10, I-12, I-13, I-15, I-16, I-18, I-19, I-21, I-22, I- 23, I-26, I-27, I-28, I-36, I-37, I-39, I-40, I-43, I-44, I-45, I-46, I-48, I-49, I-50, I-51, I-53, I-54, I-55, I-60, I-65, I-66, I-67, I-68, I-69, I- 70, I-74, I-76, I-77, I-92, I-109, I-110, I-111, I-112, I-113, I-114, I-116, I-117, I-118, I-119, I-120, I-122, I-123, I-124, I-125, I-126, I-129, I-131, I-132, I-133, I- 134, -146, I-149, I-151, I-155, I-156, I-157, I-158, I-159, I-160, I-162, I-163, I-165, I-166 I-169, I-170, I-175, I-176, I-181, I-185, I-186, I-191, I-192, I-205, I-206, I-209, I -210, I-215, I-216, I-221, I-225, I-226, I-231, I-232, I-245, I-246, I-247, I-248, I-249 I-250, I-251, I-253, I-254, I-255, I-256, I-257, I-258, I-259, I-260, I-261, I-262, I -263, I-264, I-267, I-268, I-269, I-2 0, I-271, I-272, I-273, I-274, I-275, I-277, I-278, I-280, I-282, I-283, I-285, I-286, I-288, I-289, I-290, I-291, I-292, I-293, I-294, I-295, I-296, I-297, I-298, I-299, I- 300, I-301, I-302, I-303, I-304, I-305, I-306, I-307, I-308, I-309, I-310, I-311, I-312, I-313, I-318, I-323, I-324, I-325, I-326, I-327, I-328, I-329, I-330, I-331, I-332, I- 333, I-334, I-335, I-336, I-337, I-338, I -339, I-340, II-2, II-6, II-8, II-11, II-13, II-14, II-21, II-23, II-24, II-25, II-34 II-35, II-36, II-37, II-38, II-39, II-40, II-41, II-42, II-46, II-47, II-48, II-49, II -52, II-53, II-54, II-55, II-56, II-57, II-58, II-59, II-60, II-61, II-62, II-63, II-64 II-65, II-66, II-67, II-68, II-69, II-70, II-71, II-72, II-73, II-74, II-76, II-77, II -78, II-79, II-80, II-81, II-82, II-83, II-84, II-85, II-86, II-87, II-88, II-89, II-90 II-91, II-92, II-93, II-94, II-95, II-96, II-97, II-98, II-9 II-100, II-101, II-102, II-103, II-104, II-105, II-106, II-107, II-108, II-109, II-110, II-111, II -112, II-113, II-114, II-115, II-116, II-117, II-120, II-121, II-122, II-123, II-124, II-125, II-126 II-127, II-128, II-129, II-130, II-131, II-132, II-133, II-134, II-135, II-136, II-137, III-1, III -2, III-3, III-23, III-26, III-27, III-28, III-29, III-30, III-31, III-32, III-33, III-34, III-35 III-36, III-37, III-38, IV-4, IV-33, IV-47, IV-72, IV-138, IV-147, IV-149, IV-150, IV-151, IV-152, IV-153, IV-154, IV-156, IV-157, IV-159, IV-162, IV-164, IV-167, IV-183, IV-187, IV-209, IV- 210, IV-215, IV-216, IV-218, IV-220, IV-221, IV-223, IV-224, IV-225, IV-226, IV-228, IV-229, IV-230, V-4, V-5, V-6, V-7, V-8, V-10, V-16, V-17, V-18, V-19, V-20, V-21, V- 22, V-23, V-24, V-25, V-26, V-27, V-28, V-29, V-30, V-32, V-33, V-34, V-35, V-36, V-37, V-39, V-40, V-41, V-42, V-43, V-44, V-45, V-46, V-47, V-48, V- 49, V-50, V 51, V-52, V-53, V-54, V-55, V-56, V-61, V-62, V-63, V-64, V-86, V-87, V-89, V-90, V-91, V-92, V-93, V-96, V-109, V-111, V-115, V-122, V-123, V-124, V-125, V- 126, V-127, V-128, V-129, V-130, V-131, V-132, V-133, V-134, V-135, V-136, V-137, V-138, V-139, V-140, V-141, V-142, V-143, V-144, V-145, V-146 and V-147 showed a high control effect of the criterion 7 or higher.

Test Example 2 Chinese cabbage black spot disease control test The drug prepared according to the formulation example was diluted to 200 ppm with water and sprayed on the 1.5-leaf Chinese cabbage (variety: Musou) grown in a pot. One day after spraying, a conidial spore suspension of Alcaria brassicae was spray-inoculated. Seven days after the inoculation, the degree of disease on each leaf was investigated, and the effect was determined according to the same criteria as in Test Example 1.
As a result of the above test, the compound of the present invention showed an excellent control effect at an active ingredient concentration of 200 ppm and a spray chemical amount of 50 mL. I-1, I-3, I-8, I-9, I-10, I-12, I-15, I-16, I-26, I-27, I-28, I-36, I- 37, I-41, I-43, I-45, I-46, I-48, I-49, I-51, I-53, I-54, I-55, I-60, I-65, I-66, I-67, I-68, I-69, I-70, I-74, I-76, I-77, I-92, I-109, I-110, I-111, I- 112, I-113, I-114, I-115, I-116, I-117, I-118, I-119, I-120, I-121, I-122, I-123, I-124, I-125, I-126, I-129, I-131, I-132, I-133, I-135, I-145, I-149, I-150, I-151, I-155, I- 156, I-157, I-158, I-159, I-160, I-162, I-163, I-165, I-166, I-169, I-170, I-175, I-185, I-186, I-191, I-192, I-205, I-206, I-209, I-210, I-215, I-216, I-225, I-226, I-231, I- 232, I-245, I-246, I-247, I-248, I-249, I-250, I-251, I-252, I-253, I-254, I-255, I-256, I-257, I-258, I-259, I-260, I-261, I-262, I-263, I-264, I-267, I-268, I-269, I-271, I- 272, I-273, I-274, I-275, I-280, I-283 I-284, I-285, I-286, I-287, I-288, I-289, I-290, I-291, I-292, I-293, I-294, I-295, I- 296, I-297, I-298, I-299, I-300, I-301, I-302, I-303, I-304, I-305, I-306, I-307, I-308, I-309, I-310, I-311, I-312, I-313, I-314, I-315, I-316, I-318, I-320, I-321, I-323, I- 324, I-325, I-326, I-327, I-328, I-329, I-330, I-331, I-332, I-333, I-334, I-335, I-336, I-337, I-338, I-339, I-340, II-2, II-6, II 8, II-11, II-13, II-14, II-20, II-21, II-23, II-24, II-25, II-34, II-35, II-36, II-37, II-38, II-39, II-40, II-41, II-42, II-46, II-47, II-48, II-49, II-52, II-53, II-55, II- 56, II-57, II-58, II-59, II-60, II-61, II-62, II-63, II-64, II-65, II-66, II-67, II-68, II-69, II-70, II-71, II-72, II-73, II-74, II-75, II-77, II-78, II-79, II-81, II-82, II- 83, II-84, II-85, II-86, II-87, II-88, II-89, II-90, II-91, II-92, II-93, II-94, II-95, II-96, II-97, II-98, II-99, II-100, II-101, II-102, II-103, I I-104, II-105, II-106, II-107, II-108, II-109, II-110, II-111, II-112, II-113, II-114, II-115, II- 116, II-117, II-118, II-120, II-121, II-122, II-123, II-124, II-125, II-126, II-127, II-128, II-129, II-130, II-131, II-132, II-133, II-134, II-135, II-136, II-137, III-26, III-27, III-28, III-29, III- 30, III-31, III-32, III-33, III-34, III-35, III-36, III-37, III-38, IV-161, IV-164, IV-167, IV-169, IV-183, IV-208, IV-209, IV-210, IV-215, IV-216, IV-217, IV-219, IV-222, IV-223, IV- 24, IV-226, IV-228, IV-229, IV-230, IV-231, IV-232, V-4, V-5, V-6, V-7, V-8, V-10, V-11, V-16, V-17, V-18, V-19, V-20, V-21, V-22, V-23, V-24, V-25, V-26, V- 27, V-28, V-29, V-30, V-32, V-33, V-34, V-35, V-36, V-37, V-39, V-41, V-42, V-43, V-44, V-45, V-46, V-47, V-48, V-49, V-50, V-51, V-52, V-53, V-54, V- 55, V-56, V-61, V-62, V-63, V-64, V-86, V-87, V-89, V-90, V-91, V-92, V-93, V-96, V-109, V-111, V-11 5, V-121, V-122, V-123, V-124, V-125, V-126, V-127, V-128, V-129, V-130, V-131, V-132, V-133, V-134, V-135, V-136, V-137, V-138, V-139, V-140, V-141, V-142, V-143, V-144, V- 145, V-146, and V-147 showed high activity of criteria 7 or higher.

Test Example 3 Barley powdery mildew control effect test Emulsion prepared according to Formulation Example 1 with a compound of the present invention in a 1.5-leaf barley (variety: Kanto No. 6) grown in a 6 cm diameter pot with water to a predetermined amount Diluted and sprayed with foliage. The day after spraying, the plants were sprinkled with spores obtained from barley leaves afflicted with Blumeria graminis hordei and kept in a greenhouse. Seven days after the inoculation, the control effect was determined according to the criteria of Test Example 1.

  As a result of the above test, the compound of the present invention showed an excellent control effect at an active ingredient concentration of 200 ppm and a spray chemical amount of 50 mL. I-1, I-3, I-6, I-8, I-9, I-10, I-12, I-16, I-26, I-41, I-43, I-45, I- 48, I-51, I-52, I-53, I-54, I-61, I-65, I-66, I-67, I-68, I-69, I-70, I-92, I-109, I-110, I-111, I-112, I-113, I-114, I-115, I-116, I-117, I-119, I-120, I-121, I- 122, I-123, I-124, I-129, I-131, I-132, I-134, I-146, I-149, I-150, I-155, I-156, I-157, I-158, I-159, I-160, I-162, I-163, I-165, I-166, I-169, I-175, I-176, I-181, I-185, I-186, I-191, I-192, I-205, I-206, I-209, I-210, I-215, I-216, I-225, I-226, I- 231, I-232, I-245, I-246, I-247, I-248, I-249, I-250, I-251, I-254, I-255, I-256, I-257, I-258, I-259, I-260, I-261, I-262, I-263, I-268, I-269, I-270, I-271, I-272, I-273, I- 274, I-275, I-277, I-278, I-280, I-283, I-285, I-286, I-287, I-288, I-289, I-290, I-291, I-292, I-293, I-294, I-295, I-296, I-2 7, I-298, I-299, I-300, I-301, I-302, I-303, I-304, I-305, I-306, I-307, I-308, I-309, I-310, I-311, I-312, I-313, I-314, I-315, I-318, I-323, I-324, I-325, I-326, I-327, I- 328, I-329, I-330, I-331, I-333, I-334, I-335, I-336, I-337, I-339, I-340, II-7, II-13, II-23, II-24, II-25, II-34, II-35, II-37, II-38, II-39, II-40, II-41, II-42, II-46, II- 47, II-48, II-49, II-50, II-53, II-56, II-57, II-58, II-60, II-61, II-62, II-63, I I-64, II-65, II-66, II-67, II-68, II-69, II-70, II-71, II-72, II-74, II-76, II-77, II- 78, II-79, II-80, II-82, II-83, II-84, II-85, II-86, II-87, II-88, II-89, II-90, II-91, II-92, II-93, II-94, II-95, II-96, II-97, II-98, II-99, II-100, II-101, II-102, II-103, II- 104, II-105, II-106, II-107, II-108, II-109, II-110, II-111, II-112, II-113, II-114, II-116, II-117, II-120, II-122, II-123, II-124, II-125, II-126, II-127, II-128, II-131, II-132, II-135, II-136, II- 137, III-1, III-2, III 3, III-23, III-26, III-27, III-28, III-29, III-30, III-31, III-32, III-33, III-34, III-35, III-37, III-38, IV-4, IV-7, IV-30, IV-47, IV-138, IV-147, IV-149, IV-152, IV-156, IV-159, IV-164, IV- 167, IV-169, IV-200, IV-208, IV-209, IV-210, IV-215, IV-216, IV-217, IV-219, IV-220, IV-222, IV-223, IV-224, IV-225, IV-226, IV-229, IV-230, IV-231, IV-232, V-4, V-5, V-6, V-7, V-8, V- 10, V-11, V-16, V-17, V-18, V-19, V-20, V-21, V-22, V-23, V-24, V-25, V-26, V-27, V-28, V 29, V-30, V-32, V-33, V-34, V-35, V-36, V-37, V-39, V-40, V-41, V-42, V-43, V-44, V-45, V-46, V-47, V-48, V-49, V-50, V-51, V-52, V-53, V-54, V-55, V- 56, V-61, V-62, V-63, V-64, V-86, V-87, V-89, V-90, V-91, V-92, V-93, V-96, V-109, V-111, V-115, V-121, V-122, V-123, V-124, V-125, V-127, V-128, V-129, V-131, V- 133, V-134, V-135, V-136, V-137, V-138, V-139, V-140, V-141, V-142, V-143, V-144, -145, V-146 and V-147 showed criterion 7 or more higher activity.

Test Example 4 Insecticidal test against Meloidogyne incognita Melon seedlings cultivated in pots were irrigated with a chemical solution containing a compound containing the compounds listed in Tables 1 to 5 as an active ingredient diluted to 500 ppm. One day after the drug treatment, a water suspension of nematode root-knot nematode (nematode about 500 / ml) was inoculated into the treated and untreated areas (soil irrigation), and the pot was placed in a 25 ° C. greenhouse. Eight days after the inoculation, the roots were washed with water, the number of nodules was investigated, and the effect was determined according to the following criteria.
Criteria A: No root nodules.
B: Although there are nodules, the number is clearly less than in the untreated area.
C: The number of root nodules is equal to or greater than that of the untreated section.

  I-3, I-4, I-52, I-61, I-65, I-66, I-67, I-68, I-70, I-155, I-156, I-157, I- 158, I-159, I-160, I-162, I-163, I-248, I-250, I-251, I-254, I-256, I-257, I-258, I-259, I-260, I-274, I-275, I-288, I-290, I-292, I-293, I-294, I-295, I-296, I-297, I-300, I- 301, I-305, I-307, I-308, I-314, I-325, I-326, I-327, I-328, I-329, I-331, I-333, I-339, II-24, II-25, II-41, II-64, II-67, II-74, II-79, II-80, II-81, II-90 II-91, II-92, II-93, II-94, II-106, II-107, II-110, II-112, II-113, II-118, II-122, II-123, II- 127, II-128, III-27, III-28, III-30, III-31, III-32, III-33, III-34, III-35, III-38, IV-173, IV-208, IV-209, IV-210, IV-226, IV-229, V-22, V-26, V-27, V-37, V-39, V-43, V-47, V-62, V- 63, V-86, V-87, V-90, V-96, V-123, V-129 and V-139 showed good activity of the criterion A.

The compound of the present invention is useful as a plant disease control agent that has a low burden on the global environment, has a low dose and a broad control spectrum, and exhibits an excellent control effect.

This application is based on patent application No. 2006-316296 filed in Japan, the contents of which are incorporated in full herein.

Claims (8)

Formula (I)
{Wherein R ¹ represents a ( C ₁ -C ₆ ) alkyl group ;
R ² represents a hydrogen atom .
R ³ represents a hydrogen atom.
Ar is
(1c) a phenyl group; or
(2c) (i) pyridyl group, (ii) pyrimidinyl group, (iii) pyrazinyl group, (iv) pyrazolyl group, (v) furyl group, (vi) thienyl group, (vii) oxazolyl group, (viii) isoxazolyl group , (Ix) a thiazolyl group, (x) an isothiazolyl group, and (xi) a heterocyclic group selected from a thiadiazolyl group.
X may be the same or different,
(1d) a halogen atom;
(2d) a cyano group;
(3d) a nitro group;
(4d) a (C ₁ -C ₆ ) alkyl group;
(5d) a halo (C ₁ -C ₆ ) alkyl group;
_{(6d) (C 3 -C 6} ) cycloalkyl radical;
(7d) a (C ₁ -C ₆ ) alkoxy group;
(8d) a halo (C ₁ -C ₆ ) alkoxy group;
(9d) a (C ₁ -C ₆ ) alkylthio group;
(10d) a halo (C ₁ -C ₆ ) alkylthio group;
(11d) a (C ₁ -C ₆ ) alkoxy (C ₁ -C ₆ ) alkylthio group;
(12d) a (C ₁ -C ₆ ) alkylsulfinyl group ;
_{(14d) (C 1 -C 6} ) alkylsulfonyl group;
( 16d) an amino group;
(17d) a mono (C ₁ -C ₆ ) alkylamino group;
(18d) di (C ₁ -C ₆ ) alkylamino groups which may be the same or different;
(19d) piperidino group;
(20d) may be the same or different and (i) (C ₁ -C ₆ ) alkyl group, (ii) halo (C ₁ -C ₆ ) alkyl group, (iii) (C ₁ -C ₆ ) alkoxy group, And (iv) a substituted piperidino group having one or more substituents selected from halo (C ₁ -C ₆ ) alkoxy groups;
(21d) a phenyl group ;
( 23d) a phenoxy group ;
(25d) phenyl _(C 1 -C ₆₎ alkyl group;及 beauty
(27d) shows a substituent selected from a (C ₁ -C ₆ ) alkoxyimino (C ₁ -C ₆ ) alkyl group,
n represents an integer of 1 to 5 .
Y ^1,及 Beauty ^{Y 3} may be the same or different,
(1e) a hydrogen atom;
(2e) a halogen atom ;
_{(4e) (C 1 -C 6} ) alkyl group;
(5e) a halo (C ₁ -C ₆ ) alkyl group;
(6e) a (C ₁ -C ₆ ) alkylcarbonyl group ;
(9e) _(C 1 -C ₆₎ alkoxy _(C 1 -C ₆₎ alkyl group;
(10e) a (C ₁ -C ₆ ) alkylthio group;
(11e) a halo (C ₁ -C ₆ ) alkylthio group;
(12e) a (C ₁ -C ₆ ) alkylsulfinyl group ;
_{(14e) (C 1 -C 6} ) alkylsulfonyl group;
( 16e) an amino group ;
( 22e) a phenyl group;
(23e) may be the same or different, and (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, ( v) (C ₁ -C ₆ ) alkoxy group, (vi) halo (C ₁ -C ₆ ) alkoxy group, (vii) (C ₁ -C ₆ ) alkylthio group, (viii) halo (C ₁ -C ₆ ) An alkylthio group, (ix) (C ₁ -C ₆ ) alkoxycarbonyl group, (x) phenyl group, (xi) ₁ which may be the same or different and is selected from a halogen atom and a (C ₁ -C ₆ ) alkyl group substituted phenyl group having the above substituted phenyl group having a substituent, and _{(xii) (C 1 -C 6} ) alkoxyimino _(C 1 -C ₆₎ 1 or more substituents selected from alkyl groups;
(24e) a heterocyclic group;
(25e) may be the same or different, (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, ( v) (C ₁ -C ₆ ) alkoxy group, (vi) halo (C ₁ -C ₆ ) alkoxy group, (vii) (C ₁ -C ₆ ) alkylthio group, (viii) halo (C ₁ -C ₆ ) A substituted heterocyclic group having one or more substituents selected from an alkylthio group and (ix) (C ₁ -C ₆ ) alkoxycarbonyl group ;
_{(29e) (C 1 -C 6} ) alkoxycarbonyl; and
( 31e) Phenylthio group
Represents a substituent selected pressurized et al,
Y ² is,
(1e) a hydrogen atom;
(2e) a halogen atom;
(3e) a cyano group;
(4e) a (C ₁ -C ₆ ) alkyl group;
(9e) a (C ₁ -C ₆ ) alkoxy (C ₁ -C ₆ ) alkyl group;
_{(14e) (C 1 -C 6} ) alkylsulfonyl group;
(20e) a mono (C ₁ -C ₆ ) alkylamino-carbonyl group;
(21e) di (C ₁ -C ₆ ) alkylamino-carbonyl groups which may be the same or different ;
(22e) a phenyl group;
(23e) may be the same or different, and (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, ( v) (C ₁ -C ₆ ) alkoxy group, (vi) halo (C ₁ -C ₆ ) alkoxy group, (vii) (C ₁ -C ₆ ) alkylthio group, (viii) halo (C ₁ -C ₆ ) An alkylthio group, (ix) (C ₁ -C ₆ ) alkoxycarbonyl group, (x) phenyl group, (xi) ₁ which may be the same or different and is selected from a halogen atom and a (C ₁ -C ₆ ) alkyl group substituted phenyl group having the above substituted phenyl group having a substituent, and _{(xii) (C 1 -C 6} ) alkoxyimino _(C 1 -C ₆₎ 1 or more substituents selected from alkyl groups;
(28e) carboxyl group;
_{(29e) (C 1 -C 6} ) alkoxycarbonyl group;
(30e) a halo (C ₁ -C ₆ ) alkoxycarbonyl group;
(37e) _(C 1 -C ₆₎ alkoxyimino _(C 1 -C ₆₎ alkyl group;
(38e) phenyl _(C 1 -C ₆₎ alkoxyimino _(C 1 -C ₆₎ alkyl group; and
(39e) may be the same or different and (i) a halogen atom, (ii) a cyano group, (iii) a (C ₁ -C ₆ ) alkyl group, (iv) a halo (C ₁ -C ₆ ) alkyl group, ( v) (C ₁ -C ₆ ) alkoxy group, (vi) halo (C ₁ -C ₆ ) alkoxy group, (vii) (C ₁ -C ₆ ) alkylthio group, (viii) halo (C ₁ -C ₆ ) A substituted phenyl (C ₁ -C ₆ ) alkoxyimino (C ₁ -C ₆ ) alkyl having one or more substituents selected from an alkylthio group and (ix) (C ₁ -C ₆ ) alkoxycarbonyl group on the ring Base
It shows the substituents selected from. }
A N-2- (substituted pyrazolyl) ethylcarboxamide derivative represented by the formula: Ar is a (1c) phenyl group,
X may be the same or different,
(1d) a halogen atom ;
_{(4d) (C 1 -C 6} ) alkyl group;
(5d) a halo (C ₁ -C ₆ ) alkyl group;
_{(6d) (C 3 -C 6} ) cycloalkyl group;
(7d) a (C ₁ -C ₆ ) alkoxy group;
(8d) a halo (C ₁ -C ₆ ) alkoxy group;
(9d) a (C ₁ -C ₆ ) alkylthio group; and
(10d) Halo (C ₁ -C ₆ ) alkylthio groups
Is a substituent selected pressurized et al,
N-2- (substituted pyrazolyl) ethylcarboxamide derivative or a salt of n is claim 1 Symbol placement is 1-3 integer. Ar is
(2c) (i) pyridyl group, (ii) pyrimidinyl group, (iii) pyrazinyl group, (iv) pyrazolyl group, (v) furyl group, (vi) thienyl group, (viii) isoxazolyl group, (ix) thiazolyl group And (xi) a heterocyclic group selected from thiadiazolyl groups,
X may be the same or different,
(1d) a halogen atom;
(4d) a (C ₁ -C ₆ ) alkyl group;
(5d) a halo (C ₁ -C ₆ ) alkyl group;
_{(6d) (C 3 -C 6} ) cycloalkyl group;
(7d) a (C ₁ -C ₆ ) alkoxy group; or
(9d) The N-2- (substituted pyrazolyl) ethylcarboxamide derivative or a salt thereof according to claim 1, which is a (C ₁ -C ₆ ) alkylthio group. Y ¹ 及 beauty ^{Y 3} is may be the same or different,
( 2e) a halogen atom ;
_{(4e) (C 1 -C 6} ) alkyl group; and
(5e) Halo (C ₁ -C ₆ ) alkyl groups
N-2- (substituted pyrazolyl) ethylcarboxamide derivative or a salt thereof according to any one of claims 1 to 3 is a substituent selected pressurized et al. A pest control agent comprising the N-2- (substituted pyrazolyl) ethylcarboxamide derivative or a salt thereof according to any one of claims 1 to 4 as an active ingredient. The pest control agent according to claim 5 , which is a plant disease control agent. The pest control agent according to claim 5 , which is a nematicide. A method for controlling pests, comprising treating an effective amount of the pest control agent according to any one of claims 5 to 7 on a target crop plant or soil used for cultivation of the plant.