JPH11171702A - Pest controlling method - Google Patents

Abstract

PROBLEM TO BE SOLVED: To control pest of angiosperm other than rice from the sowing to the growing stage after transplantation on a farm by a single treatment by raising a seedling in a raising seedling vessel filled with a specific raising seedling soil before sowing or provisional planting. SOLUTION: A seedling is raised before sowing or provisional planting in a raising seedling vessel filled with a raising seedling soil mixed with an agrochemical active component. The agrochemical component is preferably e.g. a compound (salt) of formula R<1a> is H, a hydrocarbon group, an acyl or an alkyl substituted with a (substituted)heterocyclic group; R<2a> is H, a hydrocarbon group or a bivalent group bonding to R<3a> ; R<3a> is a hydrocarbon group, SR<4a> (R<4a> is R<1a> ), N(R5a )(R<6a> ) (R<5a> and R<6a> are each R<1a> ) or a bivalent group bonding to R<2a> ; Y<a> is =N or =C(Z<1a> ) [Z<1a> is H or a (substituted)hydrocarbon group]; X<a> is an electron attracting group}. The angiosperm plant is e.g. plant of the order Rhoeadales, Centrospermae, Rosales, Umbelliflorae, Parietales, Malvales, Tubiflorae, Cucurbitales, Campanulatae, etc.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a new method for controlling pests, in which an active ingredient of pesticides, in particular, a non-organic phosphorus / non-carbamate penetrating insecticide compound is incorporated into an angiosperm seedling culture.

[0002]

2. Description of the Related Art In annual crops, in general, pest control during seedling raising, water management, fertilization, cultivation before planting, field management such as fertilization, pest control during the growing period after planting, fertilization, etc., from sowing to harvest. A labor-intensive operation is required.
In the case of pest control, chemical spraying is often performed several times to a dozen or more times during a single cropping season. There is also the danger of being exposed. Furthermore, it is often necessary to spray a pesticide at high temperatures, and wearing masks and work clothes is somewhat painful, so-called 3K (dangerous, dirty,
Tight work). In addition, multiple application of the drug is not preferred in terms of diffusion of the chemical into the environment. As a method of making the control of problematic pests a little easier and reducing the number of chemical treatments and the amount of treatment during a single cropping season, the technology of planting granules at the time of planting was developed for vegetables and has achieved good results. I have.

[0003]

The planting process requires a lot of time and labor since the planting process is performed one by one.
The burden is particularly heavy on large-scale farmers. For this reason, automatic transplanters that simultaneously perform planting and chemical treatment have been developed, but purchasing new machines requires a large investment for farmers. Moreover, the above-mentioned planting treatment is a method for controlling pests after planting, and there is a problem that during the seedling raising period, it is necessary to control the insects by ordinary chemical spraying. For crops with a long nursery period, it may be necessary to spray the chemical several times during the nursery period, and it is desired to develop a pest control method that can cover the period from sowing to the growing season after planting in this field with only one chemical treatment. I was

[0004]

Under such circumstances, the inventor of the present invention has proposed that before planting vegetable or flowering plants,
By applying a chemical solution containing an osmotic insecticide compound represented by the following formula [I] to a nursery bed at a high concentration and in a high dose, it is possible to treat the insect pest not only during the seedling raising period in the later stage of seedling raising, but also after planting. A method capable of controlling odors (Japanese Unexamined Patent Publication No. 9-1)
24402). As a result of further studies, it has been found that by mixing a pesticide active ingredient into the seedling cultivation soil used for sowing or the seedling cultivation used for temporary planting, it is possible to further improve the working efficiency, and complete the present invention. Reached. That is, the present invention relates to [1] a method for controlling pests on angiosperms other than rice, comprising raising seedlings in seedling containers filled with seedling cultivation soil mixed with an agricultural chemical active ingredient before sowing or provisional planting; ] The method according to the above-mentioned [1], wherein the angiosperm is a dicotyledon or a lily-ordered plant; The method of the above-mentioned (1), wherein the angiosperm plant is a Brassicaceae, an Acalyptaceae, a Papilionidae, a legume, a Rosaceae;
The method of the above-mentioned (1), which is a plant of the family Apiaceae, Violaceae, Malvaceae, Solanaceae, Labiatae, Cucurbitaceae, Asteraceae, Isopine family, Gentianaceae or Primrose family, (5) The pesticidal active ingredient is represented by the formula ( I]

Embedded image [Wherein, R ^1a represents an alkyl group substituted with a hydrogen atom, a hydrocarbon group, an acyl group or an optionally substituted heterocyclic group, and R ^2a represents a hydrogen atom, a hydrocarbon group, or a group bonded to R ^3a. R ^3a represents a hydrocarbon group, and —SR ^4a (R ^4a represents R ^1a
Is equivalent to ^{), - N (R 5a)} (R 6a) (R 5a and R ^6a are the same or different and represent the same meaning as R ^1a).
Or a divalent group or atom bonded with R ^2a, Y ^a is =
N- or = C ( ^Z1a )-( ^Z1a represents a hydrogen atom or a hydrocarbon group which may be substituted), and ^Xa represents an electron-withdrawing group. A compound represented by the following formula (I)
Is sometimes abbreviated as compound [I]. ) Or a salt thereof,
[6] R ^1a is (1) hydrogen atom, (2) C _1-6 alkyl group, (3) C
_3-10 cycloalkyl group, (4) C _2-10 alkenyl group, (5) C
_2-10 alkynyl group, (6) C _3-10 cycloalkenyl group, (7)
C _6-10 aryl group, (8) C _7-10 aralkyl group, (9) C _1-4
Alkyl-carbonyl group, (10) _C6-10 aryl-carbonyl group, (11) _C1-4 alkylsulfonyl group or (12) (i)
A C _1-6 alkyl group, (ii) a C _2-6 alkenyl group, (iii) a C _2-6
Alkynyl group, (iv) C _6-10 aryl group, (v) C _7-9 aralkyl group, (vi) nitro group, (vii) hydroxyl group, (viii) mercapto group, (ix) oxo group, (x) thioxo Group, (xi) cyano group,
(xii) carbamoyl group, (xiii) carboxyl group, (xiv) halogen, (xv) C _1-4 alkoxy group, (xvi) C _1-4 alkylthio group, (xvii) C _1-4 alkyl sulfinyl group, (xviii )
C _6-10 arylsulfinyl group, (xix) C _1-4 alkylsulfonyl group, (xx) C _6-10 arylsulfonyl group, (xxi)
Amino group, (xxii) C _1-6 acylamino group, (xxiii) mono-
Or a di-C _1-4 alkylamino group, (xxiv) a C _1-20 acyl group and (xxv) a 3- to 6-membered heterocyclic group or a fused ring group thereof with a benzene ring or a 3- to 6-membered heterocyclic ring. 1 to
It is 5 substituents are also be 3-6 membered optionally heterocyclic group substituted with or benzene ring or 3-6 membered heterocyclic ring and fused ring groups optionally substituted C _1-3 alkyl group The method according to the above [5], wherein [7] R ^2a is a hydrogen atom, a C _1-6 alkyl group, a C _3-10 cycloalkyl group, a C _2-10 alkenyl group, a C _2-10 alkynyl group, a C _3-10 Cycloalkenyl group,
A C _6-10 aryl group, a C _7-10 aralkyl group or a C _1-4 alkylene group bonded to R ^3a , —CH ₂ N (Z ^2a ) —CH ₂
A group represented by — (Z ^2a represents hydrogen, a C _1-6 alkyl group or a C _1-4 alkyl-carbonyl group) or —CH ₂ —
The method of the above-mentioned [5], which is O-CH _2- , [8] R ^3a
Is a C _1-6 alkyl group, a C _3-10 cycloalkyl group, a C _2-10
Alkenyl group, _C2-10 alkynyl group, _C3-10 cycloalkenyl group, _C6-10 aryl group, _C7-10 aralkyl group,-
SR ^{4a wherein} R ^4a is (1) a hydrogen atom, (2) a C _1-6 alkyl group,
(3) C _3-10 cycloalkyl group, (4) C _2-10 alkenyl group,
(5) C _2-10 alkynyl group, (6) C _3-10 cycloalkenyl group, (7) C _6-10 aryl group, (8) C _7-10 aralkyl group,
(9) C _1-4 alkyl - carbonyl group, (10) C _6-10 aryl - carbonyl group, (11) C _1-4 alkylsulfonyl group, or (12) (i) C _1-6 alkyl group, (ii ) A C _2-6 alkenyl group,
(iii) a C _2-6 alkynyl group, (iv) a C _6-10 aryl group, (v)
C _7-9 aralkyl group, (vi) nitro group, (vii) hydroxyl group, (vii
i) mercapto group, (ix) oxo group, (x) thioxo group, (xi)
Cyano group, (xii) carbamoyl group, (xiii) carboxyl group, (xiv) halogen, (xv) C _1-4 alkoxy group, (xvi) C
_1-4 alkylthio group, (xvii) C _1-4 alkylsulfinyl group, (xviii) C _6-10 arylsulfinyl group, (xix) C
_1-4 alkylsulfonyl group, (xx) C _6-10 arylsulfonyl group, (xxi) amino group, (xxii) C _1-6 acylamino group,
(xxiii) a mono- or di-C _1-4 alkylamino group, (xxiv)
It may be substituted with 1 to 5 substituents selected from a C _1-20 acyl group and (xxv) a 3- to 6-membered heterocyclic group or a condensed ring group thereof with a benzene ring or a 3- to 6-membered heterocyclic ring. 3 ~
And a C _1-3 alkyl group which may be substituted with a 6-membered heterocyclic group or a condensed ring group thereof with a benzene ring or a 3 to 6-membered heterocyclic ring. A group represented by the formula: -N ( ^R5a ) ( ^R6a )
[R ^5a and R ^6a are the same or different and have the same meaning as R ^4a . -S binding the base or R ^2a is represented by]
The method of the above-mentioned [5], which is-, C _1-4 alkylene or -N (Z ^3a )-(Z ^3a represents hydrogen, a C _1-6 alkyl group or a C _1-4 alkyl-carbonyl group);

[9] Y ^a is = N- or ^{= C (Z 1a) - (} Z 1a is a hydrogen atom, (i) C
_1-6 alkyl group, (ii) C _2-6 alkenyl group, (iii) C _2-6 alkynyl group, (iv) C _6-10 aryl group, (v) C _7-9 aralkyl group, (vi) nitro Group, (vii) hydroxyl group, (viii) mercapto group, (ix) oxo group, (x) thioxo group, (xi) cyano group, (xi
i) carbamoyl group, (xiii) carboxyl group, (xiv) halogen, (xv) C _1-4 alkoxy group, (xvi) C _1-4 alkylthio group, (xvii) C _1-4 alkylsulfinyl group, (xviii) C
_6-10 arylsulfinyl group, (xix) C _1-4 alkylsulfonyl group, (xx) C _6-10 arylsulfonyl group, (xxi) amino group, (xxii) C _1-6 acylamino group, (xxiii) mono - Or a di-C _1-4 alkylamino group, (xxiv) a C _1-20 acyl group and (xxv) a 3- to 6-membered heterocyclic group or a condensed ring group thereof with a benzene ring or a 3- to 6-membered heterocyclic ring. 1-5
C _1-6 alkyl group _optionally substituted with
C _3-10 cycloalkyl group, C _2-10 alkenyl group, C _2-10
Alkynyl group, C _{3 -10} cycloalkenyl group, C _6-10 aryl group or C _7-10 The method of the above-mentioned [5], wherein an aralkyl group, [10] X ^a is a cyano group, a nitro group, C _1-4 Alkoxy-carbonyl group, hydroxycarbonyl group, C
_6-10 aryl-oxycarbonyl group, 3- to 6-membered heterocyclic oxycarbonyl group, C optionally substituted with halogen
_1-4 alkylsulfonyl group, sulfamoyl group, di-C
The method of the above-mentioned [5], which is a _1-4 alkoxyphosphoryl group, a C _1-4 acyl group optionally substituted with halogen, a C _6-10 arylcarbonyl group, a carbamoyl group or a C _1-4 alkylsulfonylthiocarbamoyl. , [11]
R ^1a is a 5- or 6-membered heterocyclic group optionally substituted with a hydrogen atom, C _1-6 alkyl, formyl, C _1-4 alkylcarbonyl, C _6-10 arylcarbonyl, C _1-4 alkylsulfonyl or halogen. in a substituted C _1-3 alkyl, R ^2a is a hydrogen atom, C _1-6 alkyl, C _1-4 -CH ₂ -N binding an alkylene or _{^{R 3a (Z 2a) -CH 2}} -
(Z ^2a represents a hydrogen atom, C _1-6 alkyl or C _1-4 alkylcarbonyl) or —CH ₂ —O—CH ₂ —, wherein R ^3a is C _1-6 alkyl, —S—R ^41a (R ^41a represents a hydrogen atom, C _1-6 alkyl or C _1-4 alkylcarbonyl), —N (R ^51a ) (R ^61a ) (R ^51a and R ^51a )
^61a is the same or different and represents hydrogen or C _1-6 alkyl. ) Or C _1-4 alkylene linked to R ^2a ,
S- or ^{-N (Z 3a) - (.} Z 3a is of the same meaning as Z ^2a) is a Y ^a is = N- or = CH-, X ^a
Is nitro or cyano;
[12] The pesticidal active ingredient has the formula [II]

Embedded image [In the formula, Ar is an optionally substituted aromatic hydrocarbon group or an optionally substituted aromatic heterocyclic group, and R ^1b is a hydrogen atom, a halogen atom, nitro, cyano, carboxyl, May be a hydrocarbon group, a group via a sulfur atom or a formula

Embedded image (Wherein, X ^1b is a hydrogen atom or a carbon atom, a nitrogen atom, an oxygen atom, a group via a sulfur atom or phosphorus atom, Y ^1b
Represents a hydrogen atom or a group via a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a phosphorus atom, or X
^1b and Y ^1b combine

Embedded image Represents a nitrogen-containing heterocyclic group in which the group represented by may be substituted. R ^2b is a group through a hydrogen atom, a halogen atom or a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a phosphorus atom, and W ^b is a halogen atom or a carbon atom, a nitrogen atom, an oxygen atom, Shows a group via a sulfur atom or a phosphorus atom. (Hereinafter, the compound represented by the formula [II] may be abbreviated as the compound [II]) or a salt thereof, wherein [13] Ar is (1) Hydroxy, amino, mono- or di-C _1-6 alkylamino, C _1-6 alkoxy or a C _1-6 alkyl group optionally substituted with a halogen atom, (2) C _1-6 alkyl or C _1- alkyl ₆ amino groups optionally mono- or di-substituted with alkanoyl,
(3) hydroxyl group, (4) carboxyl group, (5) nitro group, (6) SF ₅ , (7) C _1-6 alkoxy group, (8) C _1-6 alkanoyloxy group, (9) cyano group And (10) a C _6-14 aromatic hydrocarbon group or a 5- to 8-membered aromatic heterocyclic group which may be substituted with 1 to 6 substituents selected from halogen atoms, or a C _5-10 cyclic hydrocarbon thereof. The method of the above-mentioned [12], which is a condensed ring group with hydrogen or a 5- or 6-membered heterocycle, [14] A
r is selected from halogen, C _1-6 alkyl and mono-, di- or tri-halogenated C _1-6 alkyl.
The above-mentioned [1] which is a phenyl group substituted with five substituents
2) The method described in [15] wherein R ^1b is (1) a hydrogen atom, (2) a halogen atom, (3) a nitro group, (4) a cyano group, (5) a carboxyl group, (6) (i) nitro, (ii) hydroxy, (iii) oxo,
(iv) thioxo, (v) cyano, (vi) carbamoyl, (vii) carboxyl, (viii) C _1-15 acyl group, (ix) sulfo group,
(x) a halogen atom, (xi) optionally mono-, di- or tri-halogenated (a) C _1-6 alkoxy and
(b) a C _1-14 hydrocarbonoxy group selected from C _6-14 aryloxy, (xii) -S (O) _n ^1b R ^{3b wherein} n ^1b is 0, 1
Or 2 and R ^3b represents a C _1-14 hydrocarbon group selected from C _1-6 alkyl and C _6-14 aryl. ], (Xiii) C
_1-6 alkyl or C _1-6 alkyl - mono carbonyl - or di - amino optionally substituted, (xiv) C
_Hydrazono optionally mono- or di-substituted with _1-4 alkyl and (xv) (a) halogen atom, (b) _C1-4 alkyl and (c) mono-, di- or tri-halogenated phenoxy. C _1- which may be substituted with 1 to 5 substituents selected from the group (A) consisting of a 5- or 6-membered heterocyclic group optionally having 1 to 4 substituents selected from ₂₀
A hydrocarbon group, (7) -S (O) _n ^4b R ^{16b wherein} R ^16b is a C _1-20 hydrocarbon group which may be substituted with 1 to 5 substituents selected from the group (A) or (i) a C _1-20 hydrocarbon group which may be mono-, di- or tri-halogenated, (ii) a C _1-14 hydrocarbonoxy group, (iii) a C _1-15 acyl group, (iv ) C _1-15 acyloxy group, (v) carboxyl group,
(vi) a carbamoyl group which may be mono- or di-substituted by C _1-4 alkyl, (vii) a cyclic aminocarbonyl group, (viii) a halogen atom, (ix) an oxo group, (x) an amidino group, xi) an imino group optionally substituted with C _1-6 alkyl, (xii) a C _1-6 alkyl, carbamoyl or N-mono- or N, N-di-C _1-4 alkyl-carbamoyl mono- or An amino group which may be di-substituted,
(xiii) 3 to 6-membered cyclic amino group, (xiv) C _1-6 alkanoylamido group, (xv) benzamide, (xvi) C _1-3 alkylenedioxy group, (xvii) -B (OH) 2, ( xviii) hydroxyl group, (xix) nitro group, (xx) cyano group, (xxi) -S (O) _n ^3b
R ^{11b wherein} n ^3b represents 0, 1 or 2, and R ^11b represents a hydrogen atom or a C _1-14 hydrocarbon group. And (xxii) C
1 to 1 selected from the group (B) consisting of sulfamoyl groups which may be mono- or di-substituted with _1-6 alkyl
6 substituents in optionally substituted 3- to 8-membered heterocyclic group or its C _5-10 cyclic hydrocarbon or 5-6 membered fused ring group and heterocyclic, n ^4b is integer of 0 to 2 Is shown. Or a group represented by formula (8)

Embedded image [ ^Wherein X ^1b is (i) a hydrogen atom, and (ii) C _1-20 which may be substituted with 1 to 5 substituents selected from the above group (A).
A hydrocarbon group, (iii) a C _1-24 acyl group _optionally substituted with 1 to 5 substituents selected from the group (A), (iv)
A cyano group, (v) a carbamoyl group optionally substituted with a C _1-20 hydrocarbon group _optionally substituted with 1 to 5 substituents selected from the group (A), and (vi) an amidino group , (Vi
i) a 3- to 8-membered heterocyclic group having a bond at a carbon atom which may be substituted with 1 to 5 substituents selected from the group (A) or a C _5-10 cyclic hydrocarbon or A condensed ring group with a 6-membered heterocycle, (viii) a nitro group, (ix) -NR ^4b R ^5b
[Wherein, R ^4b and R ^5b are each (a) a hydrogen atom, (b) a C _1-20 hydrocarbon group _optionally substituted with 1 to 5 substituents selected from the group (A), (c) C _{1-24 optionally} substituted with 1 to 5 substituents selected from the above group (A)
An acyl group, (d) a carbamoyl group which may be substituted with a C _1-20 hydrocarbon group which may be substituted with 1 to 5 substituents selected from the group (A), and (e) a group (B) 3 to 3 which may be substituted with 1 to 5 substituents selected from
8-membered heterocyclic group or its C _5-10 cyclic hydrocarbon or 5
A condensed ring group with a to 6-membered heterocyclic ring, (f) a hydroxyl group, (g) a C _1-20 hydrocarbon group oxy _optionally substituted with 1 to 5 substituents selected from the above group (A) Group or (h) -S
(O) _n ^2b R ^6b (R ^6b is a hydrogen atom or a C which may be substituted with 1 to 5 substituents selected from the above group (A).
_1-20 hydrocarbon group, and n ^2b represents an integer of 1-2. ). Groups represented by], (x) may be substituted with 1 to 5 substituents selected from the group (B), 3 to 8-membered heterocyclic group or its C ₅ having a bond to a nitrogen atom _-10 cyclic hydrocarbon or a condensed ring group with a 5- to 6-membered heterocyclic ring or (xi) -N ＝ C (R ^7b ) R ^{8b wherein} R ^7b and R ^8b are each a hydrogen atom, selected from the above group (A) A C _1-20 hydrocarbon group _optionally substituted with 1 to 5 substituents, a C _1-20 hydrocarbon _optionally substituted with 1 to 5 substituents selected from the above group (A) Oxy group or -N
R ^9b R ^10b (R ^9b and R ^10b each represent a hydrogen atom, a hydroxyl group or a C _1-20 hydrocarbon group which may be substituted with 1 to 5 substituents selected from the above group (A). A group represented by the formula: (xii) -OR ^{12b wherein} R ^12b is (a) a hydrogen atom, and (b) C _1- which may be substituted by 1 to 5 substituents selected from the above group (A). _{A 20-} hydrocarbon group, (c) a 3- to 8-membered heterocyclic group optionally substituted with 1 to 5 substituents selected from the group (B), or a C _5-10 cyclic hydrocarbon or 5 to 6 member thereof. A condensed ring group with a membered heterocyclic ring, (d) a C _1-24 acyl group _optionally substituted with 1 to 5 substituents selected from the above group (A), and (e) a group from the above group (A) A carbamoyl group optionally substituted with a C _1-20 hydrocarbon group _optionally substituted with 1 to 5 selected substituents, (f) -N
R ^13b R ^14b (wherein, R ^13b and R ^14b are each a hydrogen atom, a C _1-20 hydrocarbon group optionally substituted with 1 to 5 substituents selected from the above group (A), or the above group (B)
A 3- to 8-membered heterocyclic group which may be substituted by 1 to 5 substituents selected from the group consisting of: and a condensed ring group thereof with a _C5-10 cyclic hydrocarbon or a 5- to 6-membered heterocyclic ring. Or a group represented by (g) -SiR ^15b ₃ (R ^15b is a C _1-20 which may be substituted with 1 to 5 substituents selected from the group (A)).
Shows a hydrocarbon group. ). Groups represented by], (xiii) -S (O) n 4b R 16b (R 16b is 1-5 optionally substituted with a substituent C _1-20 hydrocarbon selected from the group (A) Group or a 3- to 8-membered heterocyclic group optionally substituted with 1 to 5 substituents selected from the above group (B) or its condensation with a _C5-10 cyclic hydrocarbon or a 5- to 6-membered heterocyclic ring And n ^4b represents an integer of 0 to 2;
Or (xiv) -PO (OR ^17b ) ₂ (R ^17b
_{Represents a} hydrogen atom or a C _1-15 alkyl group. A group represented by), Y ^1b is either as defined above X ^1b, or Together, with X ^1b and Y ^1b,

Embedded image May be substituted with 1 to 5 substituents selected from the group (A) and optionally substituted with 1 to 3 C _1-20 hydrocarbon groups or oxo groups. Nitrogen 5
Shows an 8-membered heterocyclic group. [1]
2] the method of [16], wherein R ^1b is a cyano group or a formula

Embedded image [Wherein, X ^1b represents a group represented by —NR ^20b R ^21b (R ^20b and R ^21b each represent a hydrogen atom, hydroxy, C _1-6 alkanoyl or C _1-6 alkyl), and Y ^1b represents hydrogen. Mono-atomic, hydroxyl, C _1-6 alkoxy
Or a C _1-6 alkoxy group which may be di-substituted, a C _1-6 alkanoyloxy group which may be mono-, di- or tri-substituted by a halogen atom, mono- or di-C _1-6 An alkyl-carbamoyloxy group,
A C _1-6 alkoxy-carbonyloxy group, a C _6-14 aryl-carbonyloxy group optionally substituted with C _1-6 alkyl, a formula —NR ^22b R ^23b , wherein R ^22b and R ^22b
23b represents a hydrogen atom, a C _1-6 alkyl group, a C _1-6 alkanoyl group or a C _1-6 alkoxy-carbonyl group, respectively. ), A C _1-6 alkyl group, or X
^1b and Y ^1b combined

Embedded image (R ^24b represents a hydrogen atom or a C _1-6 alkyl group.) [1]
2) The method described in [17] wherein R ^2b is (1) a hydrogen atom, and (2) C ₁ which may be substituted with 1 to 5 substituents selected from the group (A) described in [15]. _-20 hydrocarbon group, (3) C _1-24 acyl group _optionally substituted with 1 to 5 substituents selected from group (A) according to [15], (4) cyano group, 5) 1 to 5 selected from the group (A) according to the above [15].
A carbamoyl group optionally substituted with a C _1-20 hydrocarbon group _optionally substituted with 5 substituents, (6) an amidino group, (7) selected from the group (A) according to the above [15]. 1
A 3- to 8-membered heterocyclic group having a bond at a carbon atom which may be substituted by five substituents or a condensed ring group thereof with a C _5-10 cyclic hydrocarbon or a 5- to 6-membered heterocyclic ring, (8 ) A nitro group, (9) -NR ^4b R ^{5b wherein} R ^4b and R ^5b are each (a) a hydrogen atom; C _{1-20 optionally} substituted with a substituent
A hydrocarbon group, (c) a C _1-24 acyl group which may be substituted with 1 to 5 substituents selected from the group (A) described in the above [15], and (d) a C _1-24 acyl group described in the above [15]. A carbamoyl group optionally substituted with a C _1-20 hydrocarbon group _optionally substituted with 1 to 5 substituents selected from the group (A), (e) the group (B) according to the above [15], Or a 3- to 8-membered heterocyclic group optionally substituted with 1 to 5 substituents selected from
_5-10 cyclic hydrocarbon or a condensed ring group with a 5- to 6-membered heterocyclic ring, (f) a hydroxyl group, (g) substituted with 1 to 5 substituents selected from the group (A) described in the above [15]. An optionally _substituted C _1-20 hydrocarbon group oxy group or (h) -S
(O) _n ^2b R ^6b (R ^6b represents a hydrogen atom or a C _1-20 hydrocarbon group which may be substituted with 1 to 5 substituents selected from the group (A) described in [15] above) and n ^2b represents an integer of 1 to 2.). A group represented by
(10) 1 to 5 selected from the group (B) according to the above [15].
A 3- to 8-membered heterocyclic group having a bond at the nitrogen atom or a condensed ring group thereof with a C _5-10 cyclic hydrocarbon or a 5- to 6-membered heterocyclic ring, ) −
N ＝ C (R ^7b ) R ^8b [R ^7b and R ^8b are each a hydrogen atom and C _1- which may be substituted with 1 to 5 substituents selected from the group (A) described in the above [15]. _{A 20} hydrocarbon group, a C _1-20 hydrocarbonoxy group optionally substituted with 1 to 5 substituents selected from the group (A) according to the above [15], or -NR ^9b R ^10b (R ^9b and R ^10b is a hydrogen atom, a hydroxyl group or the group (A) according to the above [15].
A C _1-20 hydrocarbon group which may be substituted with 1 to 5 substituents selected from A group represented by the formula (12)-
OR ^{12b wherein} R ^12b is (a) a hydrogen atom, (b) a C _1-20 hydrocarbon group which may be substituted with 1 to 5 substituents selected from the group (A) according to the above [15], (c) a 3- to 8-membered heterocyclic group optionally substituted with 1 to 5 substituents selected from the group (B) described in the above [15], or a C _5-10 cyclic hydrocarbon or 5 to 6 member thereof. A condensed ring group with a membered heterocyclic ring, (d)
5] a C _1-24 acyl group _optionally substituted with 1 to 5 substituents selected from the group (A) described above;
A carbamoyl group optionally substituted with a C _1-20 hydrocarbon group _optionally substituted with 1 to 5 substituents selected from the group (A) described above, (f) -NR ^13b R ^14b (formula Wherein R ^13b and R ^14b are each a hydrogen atom, a C _1-20 hydrocarbon group optionally substituted with 1 to 5 substituents selected from the group (A) described in the above [15], or the above [15] A 3- to 8-membered heterocyclic group which may be substituted with 1 to 5 substituents selected from the group (B) described above, or its condensation with a C _5-10 cyclic hydrocarbon or a 5- to 6-membered heterocyclic ring Or a group represented by (g) -SiR ^15b ₃ (R ^15b is the above [15]
And a C _1-20 hydrocarbon group which may be substituted with 1 to 5 substituents selected from the group (A) described above. ). (13) -S (O) _n ^4b R
^16b (R ^16b is a carbon atom which may be substituted with 1 to 5 substituents selected from the group (A) described in the above [15].
_1-20 hydrocarbon group or group (B) according to the above [15]
A 3- to 8-membered heterocyclic group which may be substituted with 1 to 5 substituents selected from or a condensed cyclic group thereof with a C _5-10 cyclic hydrocarbon or a 5- to 6-membered heterocyclic ring, n ^4b represents Shows an integer of 0 to 2. ) Or (14) -PO (OR
^17b ) _{2 wherein} R ^17b represents a hydrogen atom or a C _1-15 alkyl group.
[18] R ^2b is -NR ^25b R ^{26b wherein} R ^25b and R
^26b is (1) hydrogen atom, (2) C _1-6 alkyl, (3) C _7-20 aralkyl _optionally substituted with benzoyl,
(4) mono- or di-C _1-6 alkyl-carbamoyl group, (5) C _1-6 alkanoyl optionally substituted with halogen, (6) C _6-14 arylcarbonyl or (7) C _1-6 Shows alkoxy-carbonyl. Or a group represented by-
N = C (R ^27b ) R ^{28b wherein} R ^27b and R ^28b are each substituted by (1) hydrogen atom, (2) C _1-6 alkyl group, (3) C _1-4 alkoxy and / or hydroxy C _6-14 aryl group, (4) C _1-6 alkoxy group, (5) mono-
Or a di-C _1-6 alkylamino group or (6) hydroxyamino group. [1]
2] The method described in [19] wherein W ^b is (1) -S (O) _n ^5b R ^48b
[In the formula, n ^5b represents an integer of 0 to 2, and R ^48b represents a C _1-6 alkyl group ^optionally substituted with halogen. (2) a C _1-6 alkanoyl group optionally substituted by halogen or C _1-6 alkylthio, or (3)

Embedded image [ ^Wherein , X ^2b represents an optionally substituted haloalkyl group, X ^3b represents a hydrogen atom or a group via a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a phosphorus atom, and Y ^2b represents a nitrogen atom, an oxygen atom. Or a group via a sulfur atom or a phosphorus atom, or X ^3b and Y ^2b may form a thioxo group, a hydroxyimino group or an oxirane ring,
R ^2b and Y ^2b each may be substituted with at least one heteroatom selected from an oxygen atom, a nitrogen atom, a sulfur atom or a phosphorus atom, and
_2-4, which may form a _2-4 alkylene group or a C _2-4 alkenylene group], wherein [20] X ^2b is a halo C _1-6 alkyl group, X ^3b But (1)
A hydrogen atom, or (2) (i) halogen, (ii) hydroxy, (i
ii) C _1-6 alkylthio group, (iv) C _1-6 alkoxy group, (v)
-NR ^29b R ^30b [R ^29b and R ^30b each represent a hydrogen atom, a C _1-6 alkyl group, a C _1-6 alkanoylamino group or a C _7-20 aralkyl group. A group represented by the formula (vi)
—PO (OR ^31b ) ₂ [R ^31b represents a C _1-6 alkyl group. Or a group represented by the formula (vii), which may be substituted by 1 to 3 substituent (s) selected from a 5- to 6-membered heterocyclic group:
_1-6 alkyl group, Y ^2b is (1) hydroxyl group, (2) (i) C
_1-6 alkoxy, (ii) C _1-6 alkoxycarbonyl (eg,
Methoxycarbonyl, ethoxycarbonyl, etc.) or (i
ii) a C _1-6 alkoxy group optionally substituted with mono- or di-C _1-6 alkylamino, (3) a C _2-10 alkenyloxy group, (4) a C _3-6 cycloalkyloxy group, (5) C _1-6
Carbamoyloxy group optionally substituted with alkyl or C _6-14 aryl, (6) C _1-6 alkanoyloxy group optionally substituted with halogen, (7) substituted with halogen or C _1-6 alkyl An optionally _substituted C _6-14 aryloxy group, (8) a C _1-6 alkoxycarbonyloxy group,
(9) C _6- optionally substituted with (i) C _1-6 alkyl, (ii) cyano, (iii) halogen, or (iv) mono-, di- or tri-halogeno C _1-6 alkyl. ₁₄ arylcarbonyloxy group, C _{6-14 optionally} substituted with (10) nitro
Aryloxycarbonyloxy group, (11) C _1-6 alkoxycarbonylaminooxy group, (12) C _7-20 aralkyloxy group optionally substituted with benzoyl, formula (13)

Embedded image [Wherein, R ^32b and R ^33b each represent (i) a C _6-14 aryl group optionally substituted with halogen or (ii) a C _1-6
Shows an alkyl group. A group represented by the formula (14)
(R ^34b ) _{3 wherein} R ^34b represents a C _1-6 alkyl group. ]
And (15) a substituent selected from (i) C _1-6 alkyl, (ii) C _1-6 alkylthio and (iii) oxo.
A 5- or 6-membered heterocyclic-oxy group or a condensed ring group of a 5- or 6-membered heterocyclic ring and a benzene ring,
6) 5 to 6 which may be substituted by 1 to 3 substituents selected from (i) C _1-6 alkyl, (ii) acetylamino, (iii) oxo, (iv) halogen and (v) hydroxy. membered heterocyclic group, or fused ring group and its benzene ring or a 5-6 membered heterocyclic ring, (17) -NR ^35b R ^36b wherein, R ^35b and R ^36b
Each (i) a hydrogen atom, (ii) a hydroxyl group, (iii) cyano, halogen, C _1-6 alkoxycarbonyl or mono- - may be substituted by or di -C _1-6 alkylamino C _1-6 An alkyl group, (iv) a C _6-14 aryl group optionally substituted with 1 to 3 halogens or C _1-6 alkyl, (v) a C _1-6 alkanoyl group optionally substituted with halogen, ( vi) C _1-6 alkoxy group, (vii) C _7-20 aralkyloxy group, (viii) C _1-6 alkoxycarbonyl group, (i
x) a mono- or di-C _1-6 alkylcarbamoyl group,
(x) a C _2-10 alkynyl group, (xi) a C _6-14 arylsulfonyl group optionally substituted with halogen, (xii) a C _1-6 alkylsulfonyl group optionally substituted with halogen,
(xiii) a C _1-6 alkylsulfinyl group optionally substituted with halogen, (xiv) a C _6-14 arylsulfonylamino group _optionally substituted with C _1-6 alkyl, (xv) C _1-6
It represents an alkanoylamino group or (xvi) C _1-6 alkoxycarbonylamino group. A group represented by the formula (18):
ＣＲCR ^37b R ^{38b wherein} R ^37b and R ^38b are each a hydrogen atom, a C _1-6 alkyl group, a C _1-6 alkoxy group or a C _{1-6
6-14 represents an} aryl group. (19) a C _1-6 alkylthio group optionally substituted with halogen or C _1-6 alkoxycarbonyl, (20) a C _6-14 arylthio group,

Embedded image Wherein W ^c is O or S, and R ^39b is a group represented by the formula —NR ^40b R ^41b
(Each R ^40b and R ^41b showing a C _1-6 alkyl group.) A group represented by a C _1-6 alkyl group or a C _1-6 alkoxy group. (22) C _6-14 arylsulfonyl group, (23) C _1-6 alkylsulfonyl group,
(24) C _1-6 alkylsulfinyl group, (25) (i) cyano, (i
i) C _1-6 alkoxycarbonyl and (iii) (a) C _6-14 aryl optionally substituted with halogen and / or
(b) a C _1-6 alkyl group optionally substituted with 1 to 3 substituents selected from a carbamoyl group optionally substituted with C _1-6 alkyl, or (26) a formula -PO (R ^42b )
₂ (wherein, R ^42b is. Showing a C _1-6 alkoxy group) a group represented by or R ^2b and Y ^2b and by the formula -Z ^2b -CR ^{43 b,}
R ^44b -NR ^45b-wherein R ^43b , R ^44b and R ^45b are hydrogen or a C _1-6 alkyl group, Z ^2b is an oxygen atom or -NR ^46b- (R ^46b is hydrogen or C _1-6 alkyl Represents a group). A group represented by the formula:
Z ^2b -CR ^47b = N- wherein R ^47b is hydrogen, a C _1-6 alkyl group or an amino group, and Z ^2b is as defined above. A group represented by the formula: -N = CR ^43b -NR ^44b-
(Wherein R ^43b and R ^44b are as defined above), or a group represented by the formula Z ^2b -C (= W ^d ) -NR ^44b-
[Wherein, R ^44b and Z ^2b have the same meaning as described above, and W ^d represents an oxygen atom or a sulfur atom. [21] The method according to the above [19], wherein the agrochemical active ingredient is (1) 1
-[N- (6-chloro-3-pyridylmethyl) -N-ethylamino] -1-methylamino-2-nitroethylene, (2) 1- (2-chloro-5-thiazolylmethyl)-
3-methyl-2-nitroguanidine, (3) 1- (6-chloro-3-pyridylmethyl) -N-nitro-imidazolidine-2-ylideneamine, (4) N- (6-chloro-3
-Pyridylmethyl) -N'-cyano-N-methylacetamidine, (5) 1- (2-chloro-5-thiazolylmethyl) -3,5-dimethyl-2-nitroimino-hexahydro-1,3,5-triazine , (6) 1- (3-tetrahydrofuranylmethyl) -3-methyl-2-nitroguanidine, (7) 3- (2-chloro-5-thiazolylmethyl) -5-methyl-4-nitroimino-1,3,3. 5-perhydrooxadiazine, (8) 3- (2-chloro-5-
Pyridylmethyl) -1,3-thiazolidine-2-ylidenecyanamide or (9) 5-amino-1- (2,6-dichloro-α, α, α-trifluoro-p-tolyl) -4
-The method according to the above [1], wherein the trifluoromethylsulfinylpyrazole-3-carbonitrile is [22] the active ingredient of the formula

Embedded image Wherein the R ^1c is C _1-6 alkyl or C _1-6 haloalkyl group, a n ^c is 0, 1 or 2, X ^c is -NR ^2c R ^3c,
-N = CHOR ^4c (R ^2c and R ^3c each represent a hydrogen atom or a C _1-6 alkyl group, and R ^4c represents a C _1-6 alkyl group) or -N = CHNR ^6c R ^7c (R ^6c and R ^{7 c} represents a hydrogen atom or a C _1-6 alkyl group, respectively);
^5c represents an alkyl group which may be substituted or an acyl group which may be substituted] or a salt thereof, the method according to the above [1], wherein [23] R ^{5c may} be substituted. The above [22] which is a good carbamoyl group
The method according to [24], wherein R ^5c is (1) C _1-6 alkoxy and
Three optionally substituted C _1-6 alkyl groups, (2) C _1-6
An amino optionally substituted with 1 or 2 alkyl, C _1-6 alkoxy, phenyl or a C _2-10 alkanoyl group optionally substituted with 1 to 3 halogen atoms,
(3) C _4-10 cycloalkanoyl group, (4) phenyl with 1-2
Optionally substituted C _3-10 alkenylcarbonyl group, (5) benzoyl group, (6) C _1-6 alkyl, C _3-9 cycloalkyl, C _2-6 alkenyl, C _2-6 alkynyl, phenyl A carbamoyl group optionally substituted by 1 or 2 amino, cyclic amino, hydroxyl, formyl or C _1-6 alkoxy optionally substituted by 1 or 2 benzyl, C _1-6 alkyl, (7) cyclic amino carbonyl group or (8) C _1-6 alkoxy - method of [22], wherein a carbonyl group, [25] X ^c is -NH ₂ or -N = CHOR ^4c (R ^4c is C _1-6 alkyl [22] and [26] the method according to [22], wherein R ^1c is a trifluoromethyl group.

The pesticidal active ingredients used in the present invention include carbamates (eg, carbosulfan, benflacarb, etc.) and organic phosphorus compounds (eg, acephate,
Diazinone, dimethoate, ethylthiomethone, monofurotophos, etc.), guanidine derivatives described in JP-A-3-157308, nitro compounds described in JP-A-2-288885, JP-A-2-288860, and JP-A-61-267575. Nitroimino compounds described in JP-A-60-218386 and nitromethylene derivatives described in JP-A-61-178981, and others, JP-A-62-81382, JP-A 2-2
No. 35881, WO91 / 04965, JP-A-8-31
1036 and Japanese Patent Application No. 9-15036. Among these, the above-mentioned compounds [I], [II] or salts thereof are preferable. Further, the above-mentioned compound [III] or a salt thereof is also preferable.

In the compound [I], examples of the hydrocarbon group represented by R ^1a include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, s-butyl,
C _1-6 alkyl such as t-butyl, pentyl and hexyl,
Such as cyclopropyl, cyclobutyl, cyclopentyl, C _3-10 cycloalkyl such as cyclohexyl, for example vinyl, allyl, 2-methylallyl, 2-butenyl, 3-butenyl, C _2-10 alkenyl such as 3-octenyl, such as ethynyl, 2 - propynyl, C _2-10 alkynyl such as 3-hexynyl, for example cyclopropenyl, cyclopentenyl, C _3-10, such as cyclohexenyl
Cycloalkenyl, for example, C _6-10 aryl such as phenyl, naphthyl and the like, and C _7-10 aralkyl such as phenyl-C _1-4 alkyl (eg, benzyl, phenylethyl) and the like can be mentioned.

The acyl group represented by R ^1a includes C _1-4 alkyl-carbonyl such as formyl, acetyl, propionyl and butyryl, C _6-10 aryl-carbonyl such as benzoyl, methylsulfonyl, ethylsulfonyl,
And C _1-4 alkylsulfonyl such as propylsulfonyl and butylsulfonyl. The heterocyclic group of the alkyl group substituted with the optionally substituted heterocyclic group represented by R ^1a includes a 3- to 6-membered ring containing 1 to 5 hetero atoms such as an oxygen atom, a sulfur atom, and a nitrogen atom. Or a condensed ring group thereof with a benzene ring or a 3- to 6-membered ring containing 1 to 5 heteroatoms such as an oxygen atom, a sulfur atom and a nitrogen atom, and specific examples thereof include thienyl (eg, 2- or 3
-Thienyl), furyl (eg, 2- or 3-furyl),
Pyrrolyl (eg, 1-, 2- or 3-pyrrolyl), pyridyl (eg, 2-, 3- or 4-pyridyl), oxazolyl (eg, 2-, 4- or 5-oxazolyl), thiazolyl (eg, 2 -, 4- or 5-thiazolyl), pyrazolyl (eg, 1-, 3-, 4- or 5-pyrazolyl), isoxazolyl (eg, 3-, 4- or 5-isoxazolyl), isothiazolyl (eg, 3-, 4- or 5-isothiazolyl), oxadiazolyl (eg, 1,
2,3-oxadiazol-4- or 5-yl, 1,
2,4-oxadiazol-3- or 5-yl, 1,
2,5-oxadiazol-3-yl, 1,3,4-oxadiazol-2-yl), thiadiazolyl (eg,
1,2,3-thiadiazol-4- or 5-yl,
1,2,4-thiadiazol-3- or 5-yl,
1,2,5-thiadiazol-3-yl, 1,3,4-
Thiadiazol-2-yl), triazolyl (eg, 1,
2,3-triazol-1-, 4- or -5-yl,
1,2,4-triazole-1-, 3-, 4- or 5
-Yl), tetrazolyl (eg, 1H or 2H-tetrazolyl), pyridyl in which a nitrogen atom has been oxidized (eg, 2-,
3- or 4-pyridyl-N-oxide), pyrimidinyl (eg, 2-, 4- or 5-pyrimidinyl), pyrimidinyl in which one or both of the nitrogen atoms have been oxidized (eg, 2
-, 4-, 5- or 6-pyrimidinyl-N-oxide), pyridazinyl (eg, 3- or 4-pyridazinyl), pyrazinyl, pyridazinyl in which one or both of the nitrogen atoms are oxidized (eg, 3-, 4- , 5- or 6-pyridazinyl-N-oxide), benzofuryl, benzothiazolyl, benzoxazolyl, triazinyl, oxotriazinyl, tetrazolo [1,5-b] pyridazinyl, triazolo [4,5-b] pyridazinyl, oxo Imidazinyl, dioxotriazinyl, pyrrolidinyl (eg, 1-, 2- or 3-pyrrolidinyl), piperidinyl (eg, 1-, 2-, 3- or 4-piperidinyl), pyranyl (eg, 2- , 3- or 4-pyranyl), thiopyranyl (eg, 2-, 3- or 4-thiopyranyl), oxazinyl (eg, 1,4 Oxazinyl), morpholinyl (eg, 2-, 3- or 4-morpholinyl), thiazinyl (eg, 1,4- or 1,3-thiazinyl), piperazinyl (eg, 1- or 2-piperazinyl), benzimidazolyl, quinolyl ( For example, 2-,
3-, 4-, 5-, 6-, 7- or 8-quinolyl),
Isoquinolyl, cinnonyl, phthalazinyl, quinazolinyl, naphthyridinyl (eg, 1,8-naphthyridinyl),
Prinyl, pterinidinyl, dibenzofuranyl, carbazolyl, acridinyl, phenanthridinyl, phenazinyl, phenothiazinyl, phenoxazinyl and the like. Preferred examples of the heterocyclic group include, for example, 2
-Or 3-furyl, 2-, 3- or 4-pyridyl,
5- or 6-membered heterocyclic groups such as 2-, 4- or 5-thiazolyl are exemplified.

These heterocyclic groups may have 1 to 5, preferably 1, identical or different substituents, such as methyl, ethyl,
C _1-6 alkyl groups such as propyl, isopropyl, butyl, isobutyl, s-butyl, t-butyl, pentyl, isopentyl, hexyl, isohexyl and the like, for example, allyl, isopropenyl, isobutenyl, 2-pentenyl,
2-hexenyl C _2-6 alkenyl group such as, for example propargyl, 2-butynyl, 3-butynyl, 3-pentynyl, 3-C _2-6 alkynyl group hexynyl, etc., for example, phenyl, C _6-10 aryl naphthyl Groups such as C _7-9 aralkyl groups such as phenyl-C _1-3 alkyl (eg, benzyl, phenethyl, phenylpropyl), nitro groups,
Hydroxyl group, mercapto group, oxo group, thioxo group, cyano group, carbamoyl group, carboxyl group, halogen (fluorine, chlorine, bromine, iodine), for example, C _1-4 alkoxy such as methoxy, ethoxy, n-propoxy, tert-butoxy Groups such as C _1-4 alkylthio groups such as methylthio, ethylthio, n-propylthio, isopropylthio, etc.
_1-4 alkylsulfinyl group, for example C _6-10 arylsulfinyl group such as phenylsulfinyl, C _1-4 alkylsulfonyl groups such as methylsulfonyl, ethylsulfonyl, C _6-10 arylsulfonyl group such as phenylsulfonyl, amino group, For example, C _1-6 acylamino groups such as C _1-6 alkanoylamino (eg, acetylamino, propionylamino, butyrylamino, isobutyrylamino), for example, methylamino, ethylamino, dimethylamino, diethylamino, methylethylamino, etc. A mono- or di-C _1-4 alkylamino group, for example C _1-6
Alkanoyl (eg, formyl, acetyl, propionyl, butyryl, isobutyryl, pentanoyl, hexanoyl), C _6-14 aryl-carbonyl (eg, benzoyl, naphthalenecarbonyl), C _1-6 alkoxy-carbonyl (eg, methoxycarbonyl, ethoxycarbonyl) , Propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl, se
c-butoxycarbonyl, tert-butoxycarbonyl), C _6-14 aryloxy-carbonyl (eg, phenoxycarbonyl), C _7-19 aralkyl-carbonyl (eg, benzylcarbonyl, phenethylcarbonyl, phenylpropylcarbonyl, etc.) _1-4 alkylcarbonyl), C _7-19 aralkyloxycarbonyl (eg, phenyl-C such as benzyloxycarbonyl)
_C1-20 acyl group such as _1-4 alkyloxycarbonyl), for example, a 3- to 6-membered ring group containing 1 to 5 heteroatoms such as an oxygen atom, a sulfur atom, a nitrogen atom or a benzene ring or an oxygen atom, A condensed ring group with a 3- to 6-membered ring containing 1 to 5 heteroatoms such as an atom or a nitrogen atom (the same as the above-mentioned heterocyclic group of the alkyl group substituted by the optionally substituted heterocyclic group) And the like.) And the like. Preferred examples of the optionally substituted heterocyclic group include, for example, a furyl, pyridyl and thiazolyl group optionally substituted by one or two halogens. Examples of the alkyl group in the alkyl group substituted with the optionally substituted heterocyclic group include C _1-3 alkyl groups such as methyl, ethyl and propyl.

[0009] R^2aAnd R^3aA hydrocarbon-based component represented by
The example body is also R^1aThe same are mentioned as preferred examples
Can be Also R^2aR represented by^3aDivalent group that binds to
As C such as ethylene and trimethylene_1-4Archire
, -CH_TwoN (Z^2a) -CH _Two− (Z^2aIs hydrogen, methyl
, Ethyl, propyl, n-butyl, isobutyl, etc.
C_1-6Alkyl, acetyl, propionyl, butyryl
Which C_1-4Indicate alkyl-carbonyl. )
Group, -CH_Two-O-CH_Two-And the like. R^3aIndicated by
-SR^4a(Where R^4aIs R^1aIs equivalent to )
And -N (R^5a) (R^6a) (R^5aAnd R^6aIs the same
Or differently, R^1aIs equivalent to )
R^4a, R^5aAnd R^6aIs R^1aA hydrogen atom exemplified in
Hydrocarbon group, acyl group or optionally substituted hetero group
And the same as the alkyl group substituted with the ring group.
You. R^3aR represented by^2aDivalent group or atom
Specific examples of the child include -S-, methylene, ethylene and the like.
C_1-4Alkylene, -N (Z^3a)-(Z^3aIs Z^2aAgree with
In other words, specific examples include the same. )
Groups. Y^a= C (Z^1a)-
(Z^1aRepresents a hydrogen atom or a hydrocarbon group. )
In the group^1aAs an example of a hydrocarbon group represented by
Is R^1aThe same as the hydrocarbon groups exemplified in
And the substituent of the hydrocarbon group includes the aforementioned R^1a
Substituted with an optionally substituted heterocyclic group
Same as those mentioned as the substituent of the heterocyclic group in the group
And the like. The number of the substituents is preferably 1 to 5,
Or one to three.

[0010] As the electron withdrawing group represented by X ^a, for example, cyano, nitro, such as methoxycarbonyl, C _1-4 alkoxy such as ethoxy carbonyl - C _6-10 aryl, such as carbonyl, carboxyl, for example, phenoxycarbonyl - oxy Carbonyl, for example, a heterocyclic oxycarbonyl such as pyridyloxycarbonyl, thienyloxycarbonyl or the like (the heterocyclic group is a heterocyclic group mentioned as the heterocyclic group in the alkyl group which may be substituted with the ^optionally substituted heterocyclic group of R ^1a. And _C1-4 alkylsulfonyl which may be substituted by 1 to 3 halogens such as methylsulfonyl, trifluoromethylsulfonyl and ethylsulfonyl (fluorine, chlorine, bromine and iodine). , Sulfamoyl, such as diethoxyphos Di -C _1-4 alkoxy phosphoryl Lil etc., such as acetyl, trichloroacetyl, halogen such as trifluoroacetyl (fluorine, chlorine, bromine, iodine) optionally 1-3 substituted with C
_1-4 acyl (eg, C _1-4 alkanoyl such as formyl, acetyl and the like), for example, C _6-10 arylcarbonyl such as benzoyl, carbamoyl, and C _1-4 alkylsulfonylthiocarbamoyl such as methylsulfonylthiocarbamoyl; No.

The compound [I] is an inorganic acid such as hydrochloric acid, hydrobromic acid, hydroiodic acid, phosphoric acid, sulfuric acid, perchloric acid, etc., for example, formic acid, acetic acid, tartaric acid, malic acid, citric acid, oxalic acid, Succinic acid, benzoic acid, picric acid, p-
It may be used as an agrochemically acceptable salt such as a salt with an organic acid such as toluenesulfonic acid. Specific examples of compound [I] include (i) 1- [N- (6-chloro-
3-pyridylmethyl) -N-ethylamino] -1-methylamino-2-nitroethylene, (ii) 1- (2-chloro-5-thiazolylmethyl) -3-methyl-2-nitroguanidine [N- (2 -Chloro-5-thiazolylmethyl)
-N'-methyl-N ''-nitroguanidine), (iii) 1-
(6-Chloro-3-pyridylmethyl) -N-nitro-imidazolidine-2-ylideneamine, (iv) N- (6-chloro-3-pyridylmethyl) -N'-cyano-N-methylacetamidine, ( v) 1- (6-chloro-3-pyridylmethyl) -5-methyl-2-nitroimino-hexahydro-1,3,5-triazine, (vi) 1- (2-chloro-5-thiazolylmethyl) -3, 5-dimethyl-2-nitroimino-hexahydro-1,3,5-triazine,
(vii) 1- (6-chloro-3-pyridylmethyl) -3,
5-dimethyl-2-nitroimino-hexahydro-1,
3,5-triazine, (viii) 1- (6-chloro-3-pyridylmethyl) -2-nitromethylene-imidazolidine, (ix) 1- [N- (2-chloro-5-thiazolylmethyl) -N- Ethylamino] -1-methylamino-2-nitroethylene, (x) 3- (6-chloro-3-pyridylmethyl) -2-nitromethylene-thiazolidine, (xi) 1-
(6-chloro-3-pyridylmethyl) -2- (1-nitro-2-allylthioethylidene) imidazolidine, (xi
i) 1- (6-chloro-3-pyridylmethyl) -2- (1
-Nitro-2-ethylthioethylidene) imidazolidine, (xiii) 1- (6-chloro-3-pyridylmethyl)-
2- (1-nitro-2-β-methylallylthioethylidene) imidazolidine, (xiv) methyl-[[3- (6-chloro-3-pyridylmethyl) -1-methyl-2-nitro] guanidinoformate , (Xv) 1- (6-chloro-3
-Pyridylmethylamino) -1-methylthio-2-nitroethylene, (xvi) 1- (6-chloro-3-pyridylmethylamino) -1-methylamino-2-nitroethylene, (xvii) 1- (6- Chloro-3-pyridylmethyl)-
3-nitro-2-methylisothiourea, (xviii) 3-
(6-chloro-3-pyridylmethyl) -1-methyl-2
-Nitroguanidine, (xix) 1- (6-chloro-3-pyridylmethylamino) -1-dimethylamino-2-nitroethylene, (xx) 1- [N- (2-chloro-5-pyridylmethyl)- N-methylamino] -1-methylamino-
2-nitroethylene, (xxi) 1- [N- (6-chloro-
3-Pyridylmethyl) -N-methylamino] -1-dimethylamino-2-nitroethylene, (xxii) 3- (6-chloro-3-pyridylmethyl) -1,1-dimethyl-2-
Nitroguanidine, (xxiii) 1- (6-chloro-3-pyridylmethylamino) -1-ethylamino-2-nitroethylene, (xxiv) 1-amino-1- [N- (6-chloro-3-pyridyl Methyl) -N-methylamino] -2-nitroethylene, (xxv) 3- (6-chloro-3-pyridylmethyl) -1,3-dimethyl-2-nitroguanidine,
(xxvi) 3- (6-chloro-3-pyridylmethyl) -1,
1,3-trimethyl-2-nitroguanidine, (xxvii)
1-amino-1- [N- (6-chloro-3-pyridylmethyl) -N-ethylamino] -2-nitroethylene, (x
xviii) 1- [N- (6-chloro-3-pyridylmethyl)
-N-n-propylamino] -1-methylamino-2-
Nitroethylene, (xxix) 1- [N- (6-chloro-3-
Pyridylmethyl) -N-ethylamino] -1-ethylamino-2-nitroethylene, (xxx) 3- (6-chloro-
3-pyridylmethyl) -3-ethyl-1-methyl-2-
Nitroguanidine, (xxxi) 1- (3-tetrahydrofuranylmethyl) -3-methyl-2-nitroguanidine, (x
xxii) 3- (2-chloro-5-thiazolylmethyl) -5
-Methyl-4-nitroimino-1,3,5-perhydrooxadiazine, (xxxiii) 3- (2-chloro-5-pyridylmethyl) -1,3-thiazolidine-2-ylidene cyanamide. Among them, (1) 1- [N- (6-
Chloro-3-pyridylmethyl) -N-ethylamino]-
1-methylamino-2-nitroethylene, (2) 1- (2
-Chloro-5-thiazolylmethyl) -3-methyl-2-
Nitroguanidine, (3) 1- (6-chloro-3-pyridylmethyl) -N-nitro-imidazolidine-2-ylideneamine, (4) N- (6-chloro-3-pyridylmethyl) -N'-cyano -N-methylacetamidine, (5) 1
-(2-chloro-5-thiazolylmethyl) -3,5-dimethyl-2-nitroimino-hexahydro-1,3,5
-Triazine, (6) 1- (3-tetrahydrofuranylmethyl) -3-methyl-2-nitroguanidine, (7) 3-
(2-chloro-5-thiazolylmethyl) -5-methyl-
4-nitroimino-1,3,5-perhydrooxadiazine, (8) 3- (2-chloro-5-pyridylmethyl)-
1,3-thiazolidine-2-ylidenecyanamide is preferred. Such compound [I] or a salt thereof is disclosed in JP-A-3-157308, JP-A-2-28859, JP-A-2-288860, JP-A-61-267575, JP-A-60-218386, and JP-A-61-28686. 179881,
It can be produced by the method described in JP-A-62-81382, JP-A-2-235883 or WO 91/04965 or a method analogous thereto.

The compound represented by the above formula [II] or a salt thereof may have a geometric isomer and / or a stereoisomer, and the present invention includes all the isomers and a mixture thereof. . In the above formula [II], Ar represents an optionally substituted aromatic hydrocarbon group or an optionally substituted aromatic heterocyclic group. As the aromatic hydrocarbon group in the optionally substituted aromatic hydrocarbon group represented by Ar, for example, a C _6-14 aromatic hydrocarbon group such as phenyl, naphthyl, anthryl, and phenanthryl is used. Examples of the substituent which the aromatic hydrocarbon group may have include, for example, (1) hydroxy, amino, mono- or di-C _1-6 alkylamino (eg, methylamino, ethylamino, propylamino, Dimethylamino,
Substituted with 1 to 4 C _1-6 alkoxy (eg, methoxy, ethoxy, propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy) or halogen atoms (fluorine, chlorine, bromine, iodine). A C _1-6 alkyl group (eg, methyl,
Ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, sec-pentyl, isopentyl, n-hexyl, etc.), (2) C _1-6 alkyl or C _{1- 6} amino groups optionally mono- or di-substituted with alkanoyl (eg, methylamino, ethylamino, propylamino,
Dimethylamino, diethylamino, acetylamino, propionylamino, etc.), (3) hydroxyl group, (4) carboxyl group, (5) nitro group, (6) SF _5, (7) C _1-6 alkoxy group (e.g., methoxy , Ethoxy, propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, etc.), (8) C _1-6 alkanoyloxy group (eg, formyloxy, acetyloxy, propionyloxy, n-butyryloxy, iso-butyryloxy, etc.), (9) A cyano group and (10) a halogen atom (fluorine, chlorine, bromine, iodine) and the like are used. The number of substitution is 1 to 6, preferably 1 to 4, and more preferably 1 to 3 within the range where substitution is possible. Further, particularly when the substituent is a halogen atom, it may be substituted to the maximum substitutable range.

The aromatic heterocyclic group in the optionally substituted aromatic heterocyclic group represented by Ar includes, for example,
A 5- to 8-membered aromatic heterocyclic group containing 1 to 4 heteroatoms such as an oxygen atom, a sulfur atom and a nitrogen atom other than a carbon atom or a condensed ring group thereof (for example, a C _5-10 cyclic hydrocarbon (eg, Cyclopentane, cyclohexane, benzene, naphthalene, etc.) or a condensed ring group with a 5- or 6-membered heterocyclic ring containing 1 to 4 hetero atoms such as an oxygen atom, a sulfur atom and a nitrogen atom). In particular,
For example, a 5-membered aromatic heterocyclic group containing 1 to 4 heteroatoms selected from an oxygen atom, a sulfur atom, a nitrogen atom and the like in addition to a carbon atom (eg, thienyl such as 2- or 3-thienyl, 2- or 3 Furyl, such as furyl, oxazolyl, such as 2-, 4- or 5-oxazolyl, 2-, 4-
Or thiazolyl such as 5-thiazolyl, pyrazolyl such as 3-, 4- or 5-pyrazolyl, imidazolyl such as 2-, 4- or 5-imidazolyl, isoxazolyl such as 3-, 4- or 5-isoxazolyl, 3
Isothiazolyl such as-, 4- or 5-isothiazolyl, thiadiazolyl such as 1,2,5-thiadiazolyl,
6-membered aromatic complex containing 1 to 4 heteroatoms selected from oxygen, sulfur, nitrogen, etc., in addition to carbon, other than 1,2,3-triazolyl, triazolyl such as 1,2,4-triazolyl) A ring group (eg, pyridyl such as 2-, 3- or 4-pyridyl or its N-oxide, 2
Pyrimidyl such as-, 4- or 5-pyrimidyl or its N-oxide, pyridazinyl such as 3- or 4-pyridazinyl or its N-oxide, pyrazinyl, etc.), and other than carbon atoms, oxygen, sulfur, nitrogen, etc. Bicyclic or tricyclic fused aromatic heterocyclic groups containing 1 to 4 selected heteroatoms (eg, benzofuryl, benzothiazolyl, benzoxazolyl, tetrazolo [1,
5-b] pyridazinyl, triazolo [4,5-b] pyridazinyl, imidazo [1,2-a] pyridinyl, benzimidazolyl, quinolyl, isoquinolyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, indolizinyl, quinolizinyl, 1,8-naphthyridinyl, Purinyl, pteridinyl, dibenzofuranyl, carbazolyl, acridinyl, phenanthridinyl, chromanyl, benzoxazinyl, phenazinyl, phenothiazinyl, phenoxazinyl and the like are used. As the substituent which the aromatic heterocyclic group may have, for example, the same substituents as those which the above-mentioned aromatic hydrocarbon group represented by Ar may have are used. The number of substitutions is from 1 to 6, preferably from 1 to 4, and most preferably from 1 to 3, within the substitutable range.

Examples of the halogen atom represented by R ^1b include fluorine, chlorine, bromine and iodine. The hydrocarbon group in the optionally substituted hydrocarbon group represented by R ^1b, for example, an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, an aryl group, an aralkyl group is used, among others C _{1 -20} hydrocarbon groups are preferred. Examples of the alkyl group include a C _1-15 alkyl group (eg, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl,
Undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, etc.), among which methyl, ethyl, propyl, isopropyl, butyl, t-butyl,
C _1-6 alkyl groups such as pentyl and hexyl are preferred. As the alkenyl group, for example, a C _2-10 alkenyl group (eg, vinyl, allyl, 2-methylallyl, 2-butenyl, 3-butenyl, 3-octenyl and the like) and the like are used. C _2-6 alkenyl groups such as trienyl are preferred. Examples of the alkynyl group include a C _2-10 alkynyl group (eg, ethynyl, 2-propynyl, isopropynyl, butynyl, 3-
Hexynyl and the like), among which a C _2-6 alkynyl group and the like are preferable. As the cycloalkyl, for example, a C _3-6 cycloalkyl group such as cyclopropyl, cyclopentyl and cyclohexyl is preferable. As the aryl group, for example, a C _6-14 aryl group such as phenyl, naphthyl, anthracenyl and the like are used. As aralkyl, for example, phenyl-C _1-4 alkyl (eg,
C _7-20 aralkyl groups such as benzyl, phenylethyl), benzhydryl, and trityl are used.
_7-15 aralkyl is preferred.

Examples of the substituent of these hydrocarbon groups include (1) a nitro group, (2) a hydroxyl group, (3) an oxo group,
(4) thioxo group, (5) cyano group, (6) carbamoyl group, (7)
Carboxyl group, (8) C _1-15 acyl group [for example, C _1-6 alkoxy-carbonyl (eg, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, iso-propoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, tert-butoxycarbonyl, etc.), C _1-6 alkanoyl (eg, formyl, acetyl, propionyl, n-
Butyryl, iso-butyryl, etc.), C _6-14 aryl-carbonyl (eg, benzoyl etc.), (9) sulfo group, (10) halogen atom (fluorine, chlorine, bromine, iodine), (11) mono- , Optionally di- or tri-halogenated C
_1-14 hydrocarbonoxy group [for example, C _1-6 alkoxy (eg, methoxy, ethoxy, propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, etc.),
C _6-14 aryloxy (eg, phenoxy, naphthyloxy, etc.) and the like (eg, mono-, di- or tri- such as o-, m- or p-chlorophenoxy, o-, m- or p-bromophenoxy) -Halogenated phenyloxy, etc.), (12) -S (O) _n ^1b R ^{3b wherein} n ^1b is 0, 1 or 2, and R ^3b is C _1-6 alkyl (eg, methyl, ethyl,
Propyl, isopropyl, butyl, isobutyl, sec-
Butyl, tert-butyl, pentyl, hexyl), C _6-14
And a C _1-14 hydrocarbon group such as aryl (eg, phenyl). ] [For example, C _1-6 alkylthio (eg, methylthio, ethylthio, propylthio, isopropylthio, n-
Butylthio, sec-butylthio, tert-butylthio, etc.),
C _6-14 arylthio (eg, phenylthio, etc.), C _1-6 alkylsulfinyl (eg, methylsulfinyl, ethylsulfinyl, propylsulfinyl, butylsulfinyl, etc.), C _6-14 arylsulfinyl (eg, phenylsulfinyl), C _{1 -6} alkylsulfonyl (eg, methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, etc.), C _6-14 arylsulfonyl (eg, phenylsulfonyl, etc.) and the like], (13) C _1-6 alkyl or C _1-6 Amino which may be mono- or di-substituted with alkyl-carbonyl (eg, acetylamino, propionylamino, etc.), (14) hydrazono which may be mono- or di-substituted with C _1-4 alkyl (for example, , Methylhydrazono, ethylhydrazono, dimethylhydrazono, etc.) and (15) (a) Androgenic atom (fluorine, chlorine, bromine, iodine), (b) C _1-4 alkyl (e.g., methyl, ethyl, propyl, isopropyl, etc.) and (c)
Mono-, di- or tri-halogenated phenoxy (eg, o-, m- or p-chlorophenoxy, o-,
m- or p-bromophenoxy, etc.), and 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen other than carbon, which may have 1 to 4 substituents. 5- or 6-membered heterocyclic groups (eg, thienyl such as 2- or 3-thienyl, furyl such as 2- or 3-furyl, pyrazolyl such as 3-, 4- or 5-pyrazolyl, 2-, 4- or Thiazolyl such as 5-thiazolyl, isothiazolyl such as 3-, 4- or 5-isothiazolyl, 2-, 4- or 5-
Oxazolyl, such as oxazolyl, 3-, 4- or 5
-Isoxazolyl, such as isoxazolyl, 2,4
-Or imidazolyl, such as 5-imidazolyl, 1,2,
Triazolyl such as 3- or 1,2,4-triazolyl, tetrazolyl such as 1H or 2H-tetrazolyl, pyridyl such as 2-, 3- or 4-pyridyl, 2
Pyrimidyl, such as-, 4- or 5-pyrimidyl, 3-
Or pyridazinyl such as 4-pyridazinyl, quinolyl, isoquinolyl, indolyl, etc.).
The number of substitutions is 1 to 5, preferably 1 to 3 within the range where substitution is possible.

The group via a sulfur atom represented by R ^1b will be described later. Examples of the group via a carbon atom represented by X ^1b or Y ^1b include all groups bonded via a carbon atom, and examples thereof include an optionally substituted hydrocarbon group and an optionally substituted acyl group. , A cyano group, an optionally substituted carbamoyl group, an amidino group, or an optionally substituted heterocyclic group having a bond at a carbon atom. Examples of the optionally substituted hydrocarbon group include the same as the aforementioned ^optionally substituted hydrocarbon group for R ^1b .

As the acyl group in the optionally substituted acyl group, an acyl group derived from a C _1-24 aliphatic carboxylic acid and the like are used. Specifically, for example,
A C _1-6 alkanoyl group such as formyl, acetyl, ethylcarbonyl, propylcarbonyl, tert-butylcarbonyl, etc .;
_1-6 alkoxy-carbonyl group; C _6-14 such as benzoyl
A C _6-14 aryloxy-carbonyl group such as an aryl-carbonyl group and benzooxycarbonyl; phenyl-C
_1-6 alkyl-carbonyl (eg, benzylcarbonyl)
C _7-15 aralkyl-carbonyl group; phenyl-C
A C _7-15 aralkyloxy-carbonyl group such as _1-6 alkyloxy-carbonyl (eg, benzyloxycarbonyl) and the like are used. Such an acyl group may have the same substituent as the substituent of the hydrocarbon group in the optionally substituted hydrocarbon group exemplified for R ^1b above. The number of substitutions is 1 to 5, preferably 1 to 3 within the range where substitution is possible. As the optionally substituted carbamoyl group, for example, a carbamoyl group optionally substituted with an _optionally substituted C _1-20 hydrocarbon group and the like are used. Examples of the optionally substituted C _1-20 hydrocarbon group include the same as the aforementioned ^optionally substituted hydrocarbon group for R ^1b .

The heterocyclic group in the heterocyclic group having a bond at the carbon atom which may be substituted includes, in addition to the carbon atom, 1 to 4 heterocyclic groups selected from a nitrogen atom, an oxygen atom and a sulfur atom. A 3- to 8-membered ring group containing an atom or a fused ring group thereof (eg, a C _5-10 cyclic hydrocarbon (eg,
Cyclopentane, cyclohexane, benzene, naphthalene, etc.) or a condensed ring group with a 5- or 6-membered heterocyclic ring containing 1 to 4 hetero atoms such as an oxygen atom, a sulfur atom and a nitrogen atom). Specifically, for example, 2-
Or thienyl such as 3-thienyl, furyl such as 2- or 3-furyl, pyrrolyl such as 2- or 3-pyrrolyl, pyridyl such as 2-, 3- or 4-pyridyl,
Oxazolyl such as 2-, 4- or 5-oxazolyl, thiazolyl such as 2-, 4- or 5-thiazolyl, pyrazolyl such as 3-, 4- or 5-pyrazolyl, 2-, 4- or 5-imidazolyl etc. Isoxazolyl such as imidazolyl, 3-, 4- or 5-isoxazolyl, isothiazolyl such as 3-, 4- or 5-isothiazolyl, 3- or 5- (1,2,4-oxadiazolyl), 1,3,4-oxadiazolyl Oxadiazolyl, 3- or 5- (1,2,4-thiadiazolyl), 1,3,4-thiadiazolyl, 4- or 5
-(1,2,3-thiadiazolyl), thiadiazolyl such as 1,2,5-thiadiazolyl, triazolyl such as 1,2,3-triazolyl, 1,2,4-triazolyl, 1H
-Or a 5-membered ring group containing 1 to 4 hetero atoms selected from oxygen, sulfur and nitrogen atoms in addition to carbon atoms such as tetrazolyl such as 2H-tetrazolyl;
Pyridyl such as-, 3- or 4-pyridyl, N-oxidepyridyl such as N-oxide-2-, 3- or 4-pyridyl, pyrimidyl such as 2-, 4- or 5-pyrimidyl, N-oxide-2 N-oxide pyrimidyl such as-, 4- or 5-pyrimidyl, thiomorpholinyl such as 2- or 3-thiomorpholinyl, 2- or 3
Morpholinyl, such as morpholinyl, triazinyl, oxotriazinyl, 1-2 such as dioxotriazinyl;
, Optionally having oxo, triazinyl, pyrrolidinyl, piperidinyl, pyranyl, thiopyranyl, 1,4
Oxazinyl such as -oxazinyl, 1,4-thiazinyl, thiazinyl such as 1,3-thiazinyl, piperazinyl such as 2- or 3-piperazinyl, 3- or 4-
1 to 4 heteroatoms selected from an oxygen atom, a sulfur atom, a nitrogen atom and the like in addition to carbon atoms such as pyridazinyl such as pyridazinyl, pyrazinyl, N-oxidepyridazinyl such as N-oxide-3- or 4-pyridazinyl 6-membered ring groups including, for example, benzofuryl, benzothiazolyl, benzoxazolyl, tetrazolo [1,5-b] pyridazinyl, triazolo [4,5-b] pyridazinyl,
Imidazo [1,2-a] pyridinyl, benzimidazolyl, quinolyl, isoquinolyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, indolizinyl, quinolizinyl, 1,8-naphthyridinyl, purinyl, pteridinyl, dibenzofuranyl, carbazolyl,
Bicyclic containing 1 to 4 heteroatoms selected from oxygen, sulfur, nitrogen, etc. in addition to carbon such as acridinyl, phenanthridinyl, chromanyl, benzoxazinyl, phenazinyl, phenothiazinyl, phenoxazinyl or A tricyclic fused ring group or the like is used. Such a heterocyclic group having a bond at a carbon atom is represented by R ^1b
May have the same substituent as the substituent of the hydrocarbon group in the optionally substituted hydrocarbon group exemplified in the above.
The number of substitutions is 1 to 5, preferably 1 to 3 within the range where substitution is possible.

Examples of the group via a nitrogen atom represented by X ^1b or Y ^1b include all groups bonded via a nitrogen atom. For example, a nitro group, -NR ^4b R ^{5b wherein} R ^4b and R ^5b are each a hydrogen atom, a hydrocarbon group which may be substituted, an acyl group which may be substituted,
An optionally substituted carbamoyl group, an optionally substituted heterocyclic group, a hydroxyl group, an optionally substituted hydrocarbonoxy group or —S (O) _n ^2b R ^6b (where R ^6b is a hydrogen atom or a substituted A hydrocarbon group which may be
^2b represents a group represented by 1 or 2), a heterocyclic group having a bond to a nitrogen atom which may be substituted, or —N ＝ C (R ^7b ) R ^8b [ Where R
^7b and R ^8b are each a hydrogen atom, an optionally substituted hydrocarbon group, an optionally substituted hydrocarbonoxy group, or —NR ^9b R ^10b (R ^9b and R ^10b are each a hydrogen atom, a hydroxyl group, Which represents a hydrocarbon group which may be represented by the following formula :).

The optionally substituted hydrocarbon group represented by R ^4b , R ^5b , R ^6b , R ^7b , R ^8b , R ^9b or R ^{10b includes the} optionally substituted hydrocarbon group for R ^1b . The same as the groups are used. Examples of the optionally substituted hydrocarbon group of the optionally substituted hydrocarbonoxy group represented by R ^4b , R ^5b , R ^7b or R ^8b include the aforementioned R
The same thing as the hydrocarbon group which may be substituted in ^1b is used. The optionally substituted acyl group and the optionally substituted carbamoyl group represented by R ^4b or R ^5b include the optionally substituted acyl group and the optionally substituted X ^1b or Y ^2b described above. The same carbamoyl group is used. R ^4b or R
^{As the} heterocyclic group in the optionally substituted heterocyclic group represented by ^5b , the heterocyclic group which may be substituted in X ^1b or Y ^{2b and} is defined as the heterocyclic group having a bond at a carbon atom The same thing as the ring group is used. As for the substituent in the heterocyclic group, those described later are used.

The heterocyclic group in the above-mentioned heterocyclic group having a bond at the optionally substituted nitrogen atom includes, for example, a nitrogen atom, a carbon atom and one nitrogen atom.
A 3- to 8-membered ring group optionally containing 1 to 4 heteroatoms selected from an oxygen atom, a sulfur atom and the like or a condensed ring group thereof (for example, a C _5-10 cyclic hydrocarbon (eg, cyclopentane, cyclohexane , Benzene, naphthalene, etc.)
Or a condensed ring group with a 5- or 6-membered heterocyclic ring containing 1 to 4 heteroatoms such as an oxygen atom, a sulfur atom and a nitrogen atom) and having a bond at the nitrogen atom. Specifically, for example, 1H-1-pyrrolyl, 1-imidazolyl, 1-triazolyl, 1-pyrazolyl, 1-
Indolyl, 1H-1-indazolyl, 7-purinyl,
1-aziridinyl, 1-pyrrolidinyl, 1-pyrrolinyl, 1-imidazolidinyl, 2-isoxazolidinyl,
1- or 2-pyrazolidinyl, 1- or 4-piperazinyl, 3-pyrazolin-1-yl, 3-pyrazolin-
2-yl, 1-piperidinyl, 4-morpholinyl, 4-
Thiomorpholinyl and the like are used.

Examples of the substituent of the optionally substituted heterocyclic group represented by R ^4b or R ^5b and the heterocyclic group in the above-mentioned optionally substituted heterocyclic group having a bond at the nitrogen atom include 1 ) C _1-20 hydrocarbon group which may be mono-, di- or tri-halogenated [eg, C _1-6 alkyl group (eg, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl) , Tert-butyl, pentyl, hexyl), C _2-6 alkenyl group (eg,
Vinyl, allyl, 2-methylallyl, 2-butenyl, 3
-Butenyl), a C _2-6 alkynyl group (eg, ethynyl, 2
-Propynyl, isopropynyl, butynyl, t-butynyl, 3-hexynyl), C _3-6 cycloalkyl group (eg,
Cyclopropyl, cyclopentyl, cyclohexyl),
C _5-7 cycloalkenyl group (eg, cyclopentenyl, cyclohexenyl, etc.), C _7-20 aralkyl group [eg, phenyl-C _1-4 alkyl (eg, benzyl, phenylethyl), benzhydryl, trityl], C _{6 -14} aryl group (eg, phenyl, naphthyl, anthracenyl) etc.], 2)
C _1-14 hydrocarbonoxy group [eg, C _1-6 alkoxy group (eg, methoxy, ethoxy, propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy), C
_6-14 aryloxy group (eg, phenoxy, naphthyloxy) and the like (here, halogen is exemplified by fluorine, chlorine, bromine, iodine)], 3) C _1-15 acyl group [eg, C _1-6 alkanoyl group (eg, formyl, acetyl, ethylcarbonyl, propylcarbonyl, tert-butylcarbonyl), C _6-14 aryl-carbonyl group (eg, benzoyl), C _1-6 alkoxy-carbonyl group (eg, acetoxy) , Ethoxycarbonyl) etc.], 4) C
_1-15 acyloxy group [eg, C _1-6 alkanoyloxy group (eg, formyloxy, acetyloxy, propionyloxy, n-butyryloxy, iso-butyryloxy), C
_6-14 aryl-carbonyloxy group (eg, benzoyloxy etc.)], 5) carboxyl group, 6) carbamoyl group optionally mono- or di-substituted with C _1-4 alkyl (eg, N-methylcarbamoyl) , N-ethylcarbamoyl, N-propylcarbamoyl, N-isopropylcarbamoyl, N-butylcarbamoyl, N, N-dimethylcarbamoyl, N, N-diethylcarbamoyl, N, N-
Dipropylcarbamoyl, N, N-dibutylcarbamoyl, etc.), 7) cyclic aminocarbonyl group (eg, 1-aziridinylcarbonyl, 1-azetidinylcarbonyl, 1-pyrrolidinylcarbonyl, 1-piperidinylcarbonyl,
N- methylpiperazinyl carbonyl, morpholinocarbonyl, etc.), 8) a halogen atom (fluorine, chlorine, bromine, iodine), 9) an oxo group, 10) amidino group, optionally substituted by 11) C _1-6 alkyl Good imino groups (eg, methyl imino,
Ethylimino, propylimino, butylimino), 12)
C _1-6 alkyl, carbamoyl or N-mono- or N, N-di-C _1-4 alkyl-carbamoyl mono-
Alternatively, an amino group which may be di-substituted (eg, N-
Methylcarbamoylamino, N-ethylcarbamoylamino, N-propylcarbamoylamino, N-isopropylcarbamoylamino, N-butylcarbamoylamino, N, N-dimethylcarbamoylamino, N, N-diethylcarbamoylamino, N, N-dipropyl Carbamoylamino, N, N-dibutylcarbamoylamino, etc.), 13) other than a carbon atom and one nitrogen atom, an oxygen atom,
A 3- to 6-membered cyclic amino group optionally containing 1 to 3 hetero atoms selected from a sulfur atom, a nitrogen atom and the like (eg, aziridinyl, azetidinyl, pyrrolidinyl, pyrrolinyl, pyrrolyl, imidazolyl, triazolyl, imidazolidinyl, piperidino , morpholino, dihydropyridyl, N- methylpiperazinyl, N- ethylpiperazinyl, etc.), 14) C _1-6 alkanoyl amide group (eg, formamide, acetamide, trifluoroacetamide, propionylamide, butyrylamide, Isobuchi Lylamide, etc.), 15) benzamide, 16) C _1-3 alkylenedioxy group (eg, methylenedioxy, ethylenedioxy, etc.), 1
7) -B (OH) ₂ , 18) hydroxyl group, 19) nitro group, 20)
A cyano group, 21) -S (O) _n ^3b R ^{11b wherein} n ^3b is 0.1
Or 2 and R ^11b represents a hydrogen atom or a C _1-14 hydrocarbon group. [For example, mercapto group, sulfo group, sulfino group, C _1-6 alkylthio group (eg, methylthio, ethylthio, propylthio, isopropylthio, n-butylthio, sec-butylthio, tert-butylthio), C _6-14 arylthio group (Eg, phenylthio), C _1-6 alkylsulfinyl group (eg, methylsulfinyl, ethylsulfinyl, propylsulfinyl, butylsulfinyl),
C _6-14 arylsulfinyl group (eg, phenylsulfinyl), C _1-6 alkylsulfonyl group (eg, methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl), C _6-14 arylsulfonyl group (eg, phenylsulfonyl) And 22) sulfamoyl groups which may be mono- or di-substituted with C _1-6 alkyl (eg, N-methylsulfamoyl, N-ethylsulfamoyl, N-propylsulfamoyl, N- Isopropylsulfamoyl, N-butylsulfamoyl, N, N
-Dimethylsulfamoyl, N, N-diethylsulfamoyl, N, N-dipropylsulfamoyl, N, N-dibutylsulfamoyl and the like). The number of substitutions is 1 to 6, preferably 1 to 3 within the range where substitution is possible.

The group via an oxygen atom represented by X ^1b or Y ^1b includes all groups bonded via an oxygen atom. For example, -OR ^12b [R ^12b is a hydrogen atom,
An optionally substituted hydrocarbon group, an optionally substituted heterocyclic group, an optionally substituted acyl group, an optionally substituted carbamoyl group, -NR ^13b R ^14b
Wherein R ^13b and R ^14b each represent a hydrogen atom, an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group, or —SiR
^15b ₃ (R ^15b represents a hydrocarbon group which may be substituted)]. As the optionally substituted hydrocarbon group for R ^12b , R ^13b , R ^14b or R ^15b , the same as the aforementioned optionally substituted hydrocarbon group for R ^1b can be used. R ^12b, as the optionally substituted heterocyclic group represented by R ^13b or R ^14b, wherein the R ^{4 b} and R
^{The same as the optionally} substituted heterocyclic group represented by ^5b are used. The optionally substituted acyl group and the optionally substituted carbamoyl group represented by R ^12b include the optionally substituted acyl group and the optionally substituted carbamoyl group in the above X ^1b or Y ^1b . Similar ones are used.

Examples of the group via a sulfur atom represented by R ^1b , X ^1b or Y ^1b include all groups bonded through a sulfur atom. For example, it is represented by —S (O) _n ^4b R ^16b (R ^16b represents an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group, and n ^4b represents an integer of 0 to 2). Groups are used. As the ^optionally substituted hydrocarbon group for R ^16b , the same as the ^optionally substituted hydrocarbon group for R ^1b can be used. As the optionally substituted heterocyclic group represented by R ^16b , the same as the aforementioned optionally substituted heterocyclic group represented by R ^4b or R ^5b can be used.

Examples of the group via a phosphorus atom represented by X ^1b or Y ^1b include all groups bonded through a phosphorus atom. For example, a group represented by -PO (OR ^17b ) ₂ (R ^17b represents a hydrogen atom or an alkyl group) or the like is used. Examples of the alkyl group represented by R ^17b include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl,
C _1-15 alkyl groups such as undecyl, dodecyl, tridecyl, tetradecyl and pentadecyl are used.

When X ^1b and Y ^1b are combined, the expression

Embedded image The nitrogen-containing heterocyclic group of the optionally substituted nitrogen-containing heterocyclic group formed by the group represented by is selected from a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom and the like in addition to one nitrogen atom And a 5- to 8-membered nitrogen-containing heterocyclic group which may contain 1 to 3 hetero atoms. The substituent of the nitrogen-containing heterocyclic group is preferably an optionally substituted hydrocarbon group or oxo group. The number of substitutions is 1-3. Examples of the optionally substituted hydrocarbon group include the same optionally substituted hydrocarbon groups as those described above for R ^1b .

Specifically,

Embedded image [Wherein, R ^18b represents a hydrogen atom or an optionally substituted hydrocarbon group, L ^b represents an oxygen atom or a C _1-3 alkylene group (eg, methylene, ethylene, etc.), and Z ^b represents an oxygen atom or- NR ^19b- (R ^19b represents a hydrogen atom or a hydrocarbon group which may be substituted)]. Examples of the optionally substituted hydrocarbon group represented by R ^18b or R ^19b include the aforementioned R
The same thing as the hydrocarbon group which may be substituted in ^1b is used. Among them, C _1-6 alkyl groups such as methyl, ethyl and propyl are preferred.

More specifically, the nitrogen-containing heterocyclic group formed by combining X ^1b and Y ^1b includes:

Embedded image [The symbols in the formula have the same meanings as described above] and the like. Examples of the halogen atom represented by R ^2b include fluorine, chlorine, bromine, and iodine. Examples of the group via a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a phosphorus atom represented by R ^2b include the above-mentioned groups via a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a phosphorus atom in X ^1b or Y ^1b . Similar ones can be mentioned. W ^b
As the halogen atom represented by, fluorine, chlorine, bromine,
Iodine. Examples of the group via a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a phosphorus atom represented by W ^b include the group via a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a phosphorus atom in X ^1b or Y ^1b described above. Similar ones can be mentioned. (However, when the group via the carbon atom of W ^b is a methyl group, the methyl group may be the same as the above-mentioned substituent in the optionally substituted hydrocarbon group, and may be X ^2b or X ^3b described later. And / or Y ^2b
May be substituted. )

In the above formula [II], Ar is preferably an aromatic hydrocarbon group which may be substituted. The aromatic hydrocarbon group is preferably a C _6-14 aromatic hydrocarbon group (eg, C _6-14 aryl such as phenyl, naphthyl, anthryl), and more preferably a phenyl group. Examples of the substituent include a halogen atom (fluorine, chlorine, bromine, iodine), a C _1-6 alkyl group (eg, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, etc.), Mono-, di- or tri-halogenated C _1-6
Alkyl group (eg, fluoromethyl, difluoromethyl,
Trifluoromethyl and the like). The number of substituents is 1 to
Five are preferred. Ar is particularly halogen, C _1-6
Alkyl and mono -, di- - or tri - such as one to five phenyl group substituted with a substituent selected from halogenated C _1-6 alkyl groups are preferred. Ar is most preferably a 2,6-dichloro-4-trifluoromethylphenyl group. As R ^1b , (1) a hydrogen atom, (2) a cyano group, (3) a halogen (eg, fluorine, chlorine, bromine, iodine)
A C _1-6 alkyl group which may be substituted by 1 to 3 (eg, methyl, ethyl, n-propyl, isopropyl, etc.), (4) a carbamoyl group, (5) a C _1-6 alkoxy-carbonyl group ( examples include methoxycarbonyl, ethoxycarbonyl, etc.), (6) C _1-6 alkylthio group (e.g., methylthio, ethylthio, n- propylthio, isopropylthio, etc.),
(7) C _1-6 alkylsulfinyl group (eg, methylsulfinyl, ethylsulfinyl etc.), (8) C _1-6 alkylsulfonyl group (e.g., methylsulfonyl, ethylsulfonyl, etc.), (9)

Embedded image Wherein each symbol is as defined above. ] Is preferable. In particular, cyano or the formula

Embedded image (Wherein each symbol has the same meaning as described above). X ^1b is preferably a group via a nitrogen atom and a C _1-6 alkylthio group (eg, methylthio, ethylthio, etc.). In particular, a group via a nitrogen atom is preferable. Among them, -NR ^20b R ^{21b wherein} R ^20b and R ^21b are each a hydrogen atom, hydroxy, C _1-6 alkanoyl (eg, formyl, acetyl, propionyl, etc.) or C _1-6 alkyl (E.g., methyl, ethyl, propyl, isopropyl,
n-butyl, sec-butyl, tert-butyl, etc.). ] Is preferable. In particular, X ^1b represents an amino group,
Or di-methylamino group, acetylamino group, N-
A hydroxy-N-methylamino group is preferred. Y ^1b
Is preferably a hydrogen atom or a group via a carbon atom, a nitrogen atom or an oxygen atom. More specifically, Y ^1b is a hydrogen atom; a hydroxyl group, a C _1-6 alkoxy mono-
Or di - optionally substituted C _1-6 alkoxy group (e.g., methoxy, ethoxy, methoxymethoxy, dimethoxy methoxy, etc.), mono-halogen atom -, di - or tri - substituted C _{1- 6} alkanoyloxy groups (eg, formyloxy, acetyloxy, chloroacetyloxy, propionyloxy, etc.), mono- or di-C _1-6 alkyl-carbamoyloxy groups (eg, methylcarbamoyloxy, ethylcarbamoyloxy,
Dimethylcarbamoyloxy, etc.), C _1-6 alkoxy-
Carbonyloxy group (eg, methoxycarbonyloxy,
Ethoxycarbonyloxy, etc.), C _6-14 aryl-carbonyloxy group _optionally substituted with C _1-6 alkyl (eg, benzoyloxy, 4-methylbenzoyloxy, 4-ethylbenzoyloxy, 4-tert-butyl) A group via an oxygen atom such as benzoyloxy);
R ^22b R ^{23b wherein} R ^22b and R ^23b are each a hydrogen atom, a C _1-6 alkyl group (eg, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, etc.); _{It represents a 1-6} alkanoyl group (eg, formyl, acetyl, propionyl, etc.) or a C _1-6 alkoxy-carbonyl group (eg, methoxycarbonyl, ethoxycarbonyl, etc.). A group via a nitrogen atom, such as a group represented by the following: a group via a carbon atom, such as a C _1-6 alkyl group (eg, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, etc.) Are preferred.

When X ^1b and Y ^1b are combined,

Embedded image As the nitrogen-containing heterocyclic group formed by, specifically, for example,

Embedded image [R ^24b is a hydrogen atom or a C _1-6 alkyl group (eg, methyl, ethyl, propyl, isopropyl, n-butyl, sec-
Butyl, tert-butyl, etc.). ] Is preferred.

Expression

Embedded image As the group represented by, 1,2,4-oxadiazol-3-yl is most preferred. As R ^2b , a group via a nitrogen atom and a halogen atom (eg, fluorine, chlorine, bromine, iodine) are preferable. Particularly, a group via a nitrogen atom is preferable. Among them, -NR ^25b R ^{26b wherein} R ^25b and R
^26b is (1) hydrogen atom, (2) C _1-6 alkyl (eg, methyl, ethyl, n-propyl, isopropyl, etc.), (3)
C _7-20 aralkyl _optionally substituted by one benzoyl (eg, phenyl-C _1-4 alkyl such as benzyl),
(4) mono- or di-C _1-6 alkyl-carbamoyl group (eg, methylcarbamoyl, dimethylcarbamoyl, ethylcarbamoyl, etc.), (5) 1 to 3 halogens (eg, fluorine, chlorine, bromine, iodine) Optionally substituted C
_1-6 alkanoyl (eg, formyl, acetyl, propionyl, n- butyryl, isobutyryl, etc.), (6) C _6-14 arylcarbonyl (e.g., benzoyl) or (7) C _1-6 alkoxy - carbonyl (e.g., methoxy Carbonyl, ethoxycarbonyl, etc.). Or a group represented by-
N = C (R ^27b ) R ^{28b wherein} R ^27b and R ^28b are each (1) a hydrogen atom; (2) a C _1-6 alkyl group (eg, methyl, ethyl, n-propyl, isopropyl, etc.); (3) C _1-4 alkoxy group (eg, methoxy, ethoxy, etc.) and / or C _6-14 aryl group optionally substituted with 1 to 3 hydroxy groups (eg, phenyl group); (4) C _{1- 6} alkoxy groups (eg,
Methoxy, ethoxy, etc.); (5) mono- or di-C _1-6
It represents an alkylamino group (eg, methylamino, dimethylamino, ethylamino, diethylamino, etc.) or (6) a hydroxyamino group. And the like are preferred.

As W ^b , (1) a group via a sulfur atom, (2)
Halogen (eg, fluorine, chlorine, bromine, iodine) or C _1-6 alkylthio (eg, methylthio, ethylthio, etc.)
A C _1-6 alkanoyl group which may be substituted by 1 to 15 (eg, formyl, acetyl, propionyl, butyryl, isobutyryl, pentanoyl, hexainoyl, etc.), or the formula (3)

Embedded image [ ^Wherein , X ^2b represents an optionally substituted haloalkyl group, X ^3b represents a hydrogen atom or a group via a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a phosphorus atom, and Y ^2b represents a nitrogen atom, an oxygen atom. Or a group via a sulfur atom or a phosphorus atom, or X ^3b and Y ^2b may form a thioxo group, a hydroxyimino group or an oxirane ring,
R ^2b and Y ^2b each may be substituted with at least one heteroatom selected from an oxygen atom, a nitrogen atom, a sulfur atom or a phosphorus atom, and
_May form a _2-4 alkylene group or a C _2-4 alkenylene group].

The haloalkyl in the optionally substituted haloalkyl group for X ^2b includes, for example, haloC _1-6 alkyl (eg, trifluoromethyl, chlorodifluoromethyl, pentafluoroethyl, tetrafluoroethyl,
Heptafluoropropyl, nonafluorobutyl, tridecafluorohexyl, etc.). Examples of the substituent which the haloalkyl group may have include the same substituents as those in the above-mentioned hydrocarbon group which may be substituted in R ^1b . The number of substitutions is 1 to 5, preferably 1 to 3 within the range of substitutable numbers. X ^2b
Particularly preferably (C _1-6 alkyl group substituted by halogen) above the halo C _1-6 alkyl group as a. Examples of the group via a carbon atom represented by X ^3b include X ^1b or Y ^1b
And the same groups as those described above via a carbon atom. Examples of the group via a nitrogen atom, an oxygen atom, a sulfur atom or a phosphorus atom represented by X ^3b or Y ^2b include the above-mentioned X ^1b
Or the same groups as those described for the nitrogen atom, oxygen atom, sulfur atom or phosphorus atom in Y ^1b .

X ^3b is preferably a hydrogen atom or a group via a carbon atom. Particularly, (3) a hydrogen atom or (2) (i)
Halogen (eg, fluorine, chlorine, bromine, iodine), (ii) hydroxy, (iii) C _1-6 alkylthio (eg, methylthio,
Ethylthio, propylthio, isopropylthio, n-butylthio, sec-butylthio, tert-butylthio, etc.), (iv)
C _1-6 alkoxy (eg, methoxy, ethoxy, propoxy, isopropoxy, butoxy, etc.), (v) -NR ^29b R
^30b [R ^29b and R ^30b are each a hydrogen atom, C _1-6 alkyl (eg, methyl, ethyl, propyl, isopropyl,
n-butyl, sec-butyl, tert-butyl, etc.), C _1-6 alkanoylamino (eg, formylamino, acetylamino,
Propionylamino, etc.) or C _7-20 aralkyl (eg,
And phenyl-C _1-4 alkyl such as benzyl and phenethyl. ], (Vi) -PO (OR ^31b ) ₂ [R ^31b is C
_1-6 alkyl (eg, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, etc.) is shown. Or (vii) a substituent selected from a 5- to 6-membered heterocyclic group containing 1 to 4 hetero atoms selected from an oxygen atom, a sulfur atom and a nitrogen atom (eg, 1-piperidinyl, 4-morpholinyl and the like) Up to 3 optionally substituted C
_{A 1-6} alkyl group (eg, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, etc.) is preferred.

As Y ^2b , (1) a hydroxyl group, (2)
(i) C _1-6 alkoxy (eg, methoxy, ethoxy, n-propoxy, isopropoxy, etc.), (ii) C _1-6 alkoxycarbonyl (eg, methoxycarbonyl, ethoxycarbonyl, etc.) or (iii) mono- or 1 to 3 C _1-6 alkoxy groups optionally substituted with di-C _1-6 alkylamino (eg, methylamino, dimethylamino, ethylamino, diethylamino, etc.) (eg, methoxy, ethoxy, n
-Propoxy, isopropoxy, etc.), (3) C _2-10 alkenyloxy group (eg, vinyloxy, allyloxy, 2-
(4) C _3-6 cycloalkyloxy group (eg, cyclopentyloxy, cyclohexyloxy, etc.), (5) C _1-6 alkyl (eg, methyl, ethyl, n-
Propyl, isopropyl, etc.) or a C _6-14 aryl (eg, phenyl), which may be substituted with one or two carbamoyloxy groups, (6) halogen (eg, fluorine, chlorine,
C _1-6 which may be substituted with 1 to 3 bromine, iodine)
Alkanoyloxy groups (eg, formyloxy, acetyloxy, etc.), (7) halogens (eg, fluorine, chlorine, bromine,
A C _6-14 aryloxy group (eg, phenoxy and the like) which may be substituted with 1 to 3 C _1-6 alkyl (eg, methyl, ethyl, etc.), (8) C _1-6 alkoxycarbonyl Oxy group (eg, methoxycarbonyloxy, ethoxycarbonyloxy), (9) (i) C _1-6 alkyl (eg,
Methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.), (ii) cyano, (ii
i) halogen (eg, fluorine, chlorine, bromine, iodine), or (iv) mono-, di- or tri-halogeno C _1-6 alkyl (eg, fluoromethyl, difluoromethyl, trifluoromethyl, trichloromethyl, etc.) A C _6-14 arylcarbonyloxy group (e.g., benzoyloxy, etc.) which may be substituted by 1 to 3 groups;
An optionally substituted C _6-14 aryloxycarbonyloxy group (eg, phenoxycarbonyloxy, etc.), (1
1) C _1-6 alkoxycarbonylaminooxy group (eg, methoxycarbonylaminooxy, ethoxycarbonylaminooxy, etc.), (12) C _7-20 aralkyloxy group optionally substituted by benzoyl (eg, benzyloxy, etc.) Phenyl-C _1-4 alkyloxy, etc.), formula (13)

Embedded image [Wherein, R ^32b and R ^33b each represent (i) a C _6-14 aryl group (eg, phenyl) which may be substituted with 1 to 3 halogen atoms (eg, fluorine, chlorine, bromine, iodine) or ( ii) represents a C _1-6 alkyl group (eg, methyl, ethyl, n-propyl, isopropyl, etc.). A group represented by
(14) Formula -OSi (R ^34b ) _{3 wherein} R ^34b represents a C _1-6 alkyl group (eg, methyl, ethyl, n-propyl, isopropyl, etc.). (15) (i) C _1-6 alkyl (eg, methyl, ethyl, etc.), (ii) C _1-6 alkylthio (eg, methylthio, ethylthio, etc.) and (iii) oxo A 5- to 6-membered heterocyclic-oxy group having 1 to 4 hetero atoms selected from an oxygen atom, a nitrogen atom and a sulfur atom which may be substituted by 1 to 3 substituents or an oxygen atom, a nitrogen atom and a sulfur atom A condensed ring group of a 5- to 6-membered heterocyclic ring having 1 to 4 heteroatoms and a benzene ring (eg, pyrimidinyl, pyrrolidinyl, isoindolinyl, etc.), (16) (i) C _1-6 alkyl (eg, Methyl, ethyl, etc.), (ii) acetylamino, (iii) oxo, (iv) halogen (eg, fluorine, chlorine, bromine, iodine) and (v)
A 5- to 6-membered heterocyclic group having 1 to 4 heteroatoms selected from an oxygen atom, a nitrogen atom and a sulfur atom which may be substituted by 1 to 3 substituents selected from hydroxy, or a benzene ring or an oxygen atom thereof A condensed ring group with a 5- to 6-membered heterocyclic ring having 1 to 4 heteroatoms selected from a nitrogen atom and a sulfur atom (eg, isoxazolidinyl, perhydroazosinyl, aziridinyl, morpholinyl, piperidyl, pyrrolidinyl, Isoindolinyl, triazolyl, thienyl, pyrrolyl, pyrazolyl, etc.), (17)
R ^35b R ^{36b wherein} R ^35b and R ^36b are each (i) a hydrogen atom, (ii) a hydroxyl group, (iii) cyano, halogen (eg, fluorine, chlorine, bromine, iodine), C _1-6 alkoxy C 1-3 optionally substituted with carbonyl (eg, methoxycarbonyl, ethoxycarbonyl, etc.) or mono- or di-C _1-6 alkylamino (eg, methylamino, ethylamino, dimethylamino, diethylamino, etc.) _1-6 alkyl group (eg, methyl, ethyl, n-propyl, isopropyl, etc.), (iv) halogen (eg, fluorine, chlorine, bromine, iodine) or C _1-6 alkyl (eg, methyl, ethyl, n- Propyl, isopropyl, etc.)
Optionally substituted C _6-14 aryl group (eg, phenyl), (v) 1 to 3 optionally substituted C _1-6 alkanoyl with halogen (eg, fluorine, chlorine, bromine, iodine) (Eg, formyl, acetyl, etc.), (vi) C _1-6 alkoxy group (eg, methoxy, ethoxy, n-propoxy, isopropoxy, etc.), (vii) C _7-20 aralkyloxy group (eg, benzyloxy Phenyl-C _1-4 alkyloxy, etc.), (viii) C _1-6 alkoxycarbonyl group (eg, methoxycarbonyl, ethoxycarbonyl, etc.),
(ix) mono- or di-C _1-6 alkylcarbamoyl group (eg, methylcarbamoyl, ethylcarbamoyl, dimethylcarbamoyl, etc.), (x) C _2-10 alkynyl group (eg,
Ethynyl, 2-propynyl, isopropynyl, butynyl, etc.), (xi) C _6-14 arylsulfonyl group (eg, phenyl) which may be substituted with 1 to 3 halogens (eg, fluorine, chlorine, bromine, iodine) Sulfonyl, etc.), (xii) a C _1-6 alkylsulfonyl group optionally substituted with 1 to 3 halogens (eg, fluorine, chlorine, bromine, iodine) (eg,
Methylsulfonyl, ethylsulfonyl, etc.), (xiii) halogen (e.g., fluorine, chlorine, bromine, 1-3 optionally substituted C _1-6 alkyl sulfinyl group (e.g. with iodine), methylsulfinyl, ethylsulfinyl, etc. ),
(xiv) a C _6-14 arylsulfonylamino group (eg, phenylsulfonylamino) _optionally substituted with 1 to 3 C _1-6 alkyl (eg, methyl, ethyl, n-propyl, isopropyl, etc.); (xv) a C _1-6 alkanoylamino group (eg, formylamino, acetylamino, etc.) or (xv
i) represents a C _1-6 alkoxycarbonylamino group (eg, methoxycarbonylamino, ethoxycarbonylamino, etc.). Groups represented by], (18) -N = CR ^37b R ^38b wherein each of R ^37b and R ^38b hydrogen atom, C _1-6 alkyl group (e.g., methyl, ethyl, n- propyl, isopropyl, etc. ), A C _1-6 alkoxy group (eg, methoxy, ethoxy, etc.) or a C _6-14 aryl group (eg, phenyl). Represented by the formula (1), halogen (eg, fluorine, chlorine, bromine, iodine) or C _1-6 alkoxycarbonyl (eg, methoxycarbonyl, ethoxycarbonyl, etc.), which may be substituted by 1 to 3 carbon atoms. _1-6 alkylthio group (eg, methylthio, ethylthio, etc.), (20) C _6-14 arylthio group (eg, phenylthio, etc.), formula (21)

Embedded image Wherein W ^c is O or S, and R ^39b is a group represented by the formula —NR ^40b R ^41b
(R ^40b and R ^41b are each a C _1-6 alkyl group (eg,
Methyl, ethyl, n-propyl, isopropyl, etc.). ), A C _1-6 alkyl group (eg, methyl, ethyl, n-propyl, isopropyl, etc.) or C
_{1-6 represents an} alkoxy group (eg, methoxy, ethoxy, n-propoxy, isopropoxy, etc.). (22) C _6-14 arylsulfonyl group (eg, phenylsulfonyl etc.), (23) C _1-6 alkylsulfonyl group (eg,
Methylsulfonyl, ethylsulfonyl, etc.), (24) _C1-6
Alkylsulfinyl groups (eg, methylsulfinyl, ethylsulfinyl, etc.), (25) (i) cyano, (ii) C _1-6 alkoxycarbonyl (eg, methoxycarbonyl, ethoxycarbonyl, etc.) and (iii) (a) halogen ( For example, fluorine,
C _6-14 aryl (eg, phenyl, etc.) optionally substituted with 1 to 3 substituent (s) with chlorine, bromine, iodine) and / or (b)
C _1-6 alkyl (eg, methyl, ethyl, n-propyl,
C _1-6 alkyl group optionally substituted with 1 to 3 substituent (s) selected from 1 to 2 carbamoyl groups which may be substituted with 1 to 2 (eg, methyl, ethyl, n
-Propyl, isopropyl, etc.) or (26) formula -PO
A group represented by (R ^42b ) ₂ (wherein R ^42b represents a C _1-6 alkoxy group (eg, methoxy, ethoxy, etc.)) is preferable.

C ₂ -C ₂ formed by R ^2b and Y ^2b , which may be substituted and whose constituent carbon atom is substituted by at least one heteroatom selected from an oxygen atom, a nitrogen atom, a sulfur atom and a phosphorus atom. Preferred examples of the ₄ alkylene group or C _2-4 alkenylene group include those represented by the formula —Z ^2b —CR ^43b R
^44b -NR ^45b-wherein R ^43b , R ^44b and R ^45b are hydrogen or an optionally substituted hydrocarbon group, and Z ^2b is an oxygen atom or -NR ^46b- (R ^46b is hydrogen or substituted And a hydrocarbon group which may be represented by the following formula: A group represented by; formula -Z ^2b -CR ^47b = N- wherein, R ^47b represents hydrogen, a hydrocarbon may be substituted hydrogen group or an amino group, Z ^2b is as defined above. A group represented by the formula: -N = CR ^43b -NR ^44b- (wherein R ^43b
And R ^44b are as defined above. Or a group represented by the formula Z ^2b —C (＝ W ^d ) —NR ^44b —
^44b and Z ^2b are as defined above, and W ^d is an oxygen atom or a sulfur atom. A group represented by the formula:

The above R ^43b , R ^44b , R ^45b , R ^46b and R
^{The optionally} substituted hydrocarbon group represented by ^47b is the same as the aforementioned ^optionally substituted hydrocarbon group for R ^1b . Particularly, C _1-6 alkyl (eg, methyl, ethyl, etc.) is preferred. Examples of the group via a sulfur atom in W ^b include a group represented by the formula —S (O) _n ^5b R ^{48b wherein} n ^5b is 0
R ^48b is a halogen (eg, fluorine, chlorine,
C _1-6 which may be substituted with 1 to 3 bromine, iodine)
And an alkyl group (eg, methyl, ethyl, n-propyl, isopropyl, etc.). ] Is preferable.

The compound [II] is described in JP-A-63-31
No. 6771, 5-amino-1- (2,6-dichloro-α, α, α-trifluoro-p-tolyl) -4
In addition to -trifluoromethylsulfinylpyrazole-3-carbonitrile, compounds described in JP-A-8-311036 and Japanese Patent Application No. 9-15036, that is, compounds shown in Tables 1 to 36 shown below or salts thereof are preferable. Used.

[0039]

[Table 1]

[0040]

[Table 2]

[0041]

[Table 3]

[0042]

[Table 4]

[0043]

[Table 5]

[0044]

[Table 6]

[0045]

[Table 7]

[0046]

[Table 8]

[0047]

[Table 9]

[0048]

[Table 10]

[0049]

[Table 11]

[0050]

[Table 12]

[0051]

[Table 13]

[0052]

[Table 14]

[0053]

[Table 15]

[0054]

[Table 16]

[0055]

[Table 17]

[0056]

[Table 18]

[0057]

[Table 19]

[0058]

[Table 20]

[0059]

[Table 21]

[0060]

[Table 22]

[0061]

[Table 23]

[0062]

[Table 24]

[0063]

[Table 25]

[0064]

[Table 26]

[0065]

[Table 27]

[0066]

[Table 28]

[0067]

[Table 29]

[0068]

[Table 30]

[0069]

[Table 31]

[0070]

[Table 32]

[0071]

[Table 33]

[0072]

[Table 34]

[0073]

[Table 35]

[0074]

[Table 36]

Among the above-mentioned compounds [II], a particularly preferred compound is 5-amino-1- (2,6-dichloro-α,
α, α-trifluoro-p-tolyl) -4-trifluoromethylsulfinylpyrazole-3-carbonitrile, 5-amino-1- (2,6-dichloro-4-trifluoromethylphenyl) -3- (N -Hydroxy-N-
Methylamidino) -4-trifluoromethylsulfinylpyrazole, 1- (2,6-dichloro-4-trifluoromethylphenyl) -5-methoxymethylideneamino-3- (1,2,4-oxadiazole-3 -Il)-
4-trifluoromethylsulfinylpyrazole, 5-
Amino-1- (2,6-dichloro-4-trifluoromethylphenyl) -3- (1,2,4-oxadiazol-3-yl) -4-trifluoromethylsulfonylpyrazole, 5-amino-1 -(2,6-dichloro-4-trifluoromethylphenyl) -3- (1,2,4-oxadiazol-3-yl) -4-trifluoromethylsulfinylpyrazole, 1- (2,6-dichloro -4-
Trifluoromethylphenyl) -5-ethoxymethylideneamino-3- (1,2,4-oxadiazole-3-
Yl) -4-trifluoromethylsulfinylpyrazole, 1- (2,6-dichloro-4-trifluoromethylphenyl) -5-dimethylamino-3- (1,2,4-
Oxadiazol-3-yl) -4-trifluoromethylsulfinylpyrazole.

Such a compound [II] or a salt thereof is
JP-A-63-316771, JP-A-8-311036,
It can be produced by the method described in Japanese Patent Application No. 9-15036 or a method analogous thereto.

Examples of the salt of the compound [II] of the present invention include salts that are acceptable in agrochemical chemistry. That is, when the molecule has an acidic group such as a carboxyl group or a sulfo group, a salt with a base may be formed. Examples of the base include alkali metals such as sodium, potassium and lithium, calcium and magnesium. Alkaline earth metals, such as
An inorganic base such as ammonia, for example, an organic base such as pyridine, collidine, triethylamine, and triethanolamine is used. Also, for example, salts of inorganic acids such as hydrochloric acid, hydrobromic acid, hydroiodic acid, phosphoric acid, sulfuric acid, and perchloric acid, or formic acid, acetic acid, tartaric acid, malic acid, citric acid, oxalic acid, succinic acid, Benzoic acid, picric acid,
A salt of an organic acid such as methanesulfonic acid and p-toluenesulfonic acid may be used. In addition, compound [II] may form an inner salt, and in such a case, it can be used in the method of the present invention.

As another embodiment of the compound included in the compound represented by the formula [II], a compound represented by the formula [III] or a salt thereof is also preferably used. The compound represented by the above formula [III] or a salt thereof may have a geometrical isomer and / or a stereoisomer, but the present invention includes all such isomers. Examples of the C _1-6 alkyl group represented by R ^1c include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl and the like. Examples of the C _1-6 haloalkyl group represented by R ^1c include chloromethyl, fluoromethyl, bromomethyl, 2-chloroethyl, dichloromethyl, trichloromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, and pentafluoro Halogen such as ethyl, heptafluoropropyl, nonafluorobutyl (eg, fluorine, chlorine, bromine, iodine)
C _1-6 substituted with 1 to 10 (preferably 1 to 5)
An alkyl group is used. ^{R 2c, R 3c, R 4c} , as the C _1-6 alkyl group in R ^6c and R ^7c, include the same C _1-6 alkyl groups exemplified above for R ^1c.
R ^2c and R ^3c are each preferably a hydrogen atom.

Examples of the alkyl group of the ^optionally substituted alkyl group represented by R ^5c include the same groups as those exemplified above for R ^1c.
_1-6 alkyl group. Examples of the substituent of the alkyl group include a hydroxyl group, an amino group, a mono- or di-C _1-6 alkylamino group (eg, methylamino, ethylamino, propylamino, dimethylamino, diethylamino, etc.), C _1-6 Alkoxy group (eg, methoxy, ethoxy, propoxy, isopropoxy, butoxy, etc.), C
_1-4 alkylthio groups (eg, methylthio, ethylthio, n
-Propylthio, isopropylthio, butylthio, etc.),
Examples include a halogen atom (eg, fluorine, chlorine, bromine, iodine), a carboxyl group, a nitro group, a cyano group, and the like.
The number of substitutions is 1 to 6, preferably 1 to 3 within the range where substitution is possible. Examples of the acyl group of the optionally substituted acyl group represented by R ^5c include an acyl group having 1 to 20 carbon atoms derived from a carboxylic acid, for example, formyl, alkanoyl group, preferably 2 to 20 carbon atoms. 10 alkanoyl groups (eg, C _1-9 alkyl- such as acetyl, propionyl, butyryl, isobutyryl, pentanoyl, hexanoyl, heptanoyl, pivaloyl, etc.)
Carbonyl group), a cycloalkanoyl group, preferably a cycloalkanoyl group having 4 to 10 carbon atoms (eg, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.), an alkenylcarbonyl group, preferably 3 carbon atoms
To 10 alkenylcarbonyl groups (eg, acryloyl, allylcarbonyl, isopropenylcarbonyl, isobutenylcarbonyl, 1-methylallylcarbonyl,
Cinnamoyl), an alkynylcarbonyl group, preferably an alkynylcarbonyl group having 3 to 7 carbon atoms (eg, propargylcarbonyl, 2-butynylcarbonyl, 3-butynylcarbonyl, 3-pentynylcarbonyl, etc.), an arylcarbonyl group, preferably Is an aryl-carbonyl group having 6 to 14 carbon atoms (eg, benzoyl, 1-naphthoyl, 2-naphthoyl, etc.), an alkoxycarbonyl group, preferably an alkoxy-carbonyl group having 1 to 6 carbon atoms (eg, methoxycarbonyl, ethoxycarbonyl) , Propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, etc.), aryloxycarbonyl group, preferably aryloxy-carboxy having 6 to 14 carbon atoms. Nyl group (eg, phenoxycarbonyl group), aralkylcarbonyl group, preferably aralkyl-carbonyl group having 7 to 19 carbon atoms (eg, phenyl-C _1-4 alkylcarbonyl such as benzylcarbonyl, phenethylcarbonyl, phenylpropylcarbonyl, etc.) Hydrylcarbonyl, naphthyl-C _1-4 alkylcarbonyl such as 1-naphthylethylcarbonyl, etc.), an aralkyloxycarbonyl group, preferably an aralkyloxycarbonyl group having 7 to 19 carbon atoms (eg, benzyloxycarbonyl, phenethyloxycarbonyl, phenylpropyl phenyl -C _1-4 alkyloxycarbonyl, such as oxycarbonyl), a carbamoyl group, a cyclic aminocarbonyl group (e.g., 1-pyrrolidinocarbonyl, piperidinocarbonyl, morpholinocarbonyl ) And the like are used.

When the acyl group is an alkanoyl group, a cycloalkanoyl group, an alkenylcarbonyl group, an alkynylcarbonyl group, an arylcarbonyl group, an alkoxy-carbonyl group, an aryloxycarbonyl group, an aralkylcarbonyl group or an aralkyloxycarbonyl group, 1 to 6 (preferably 1 to 3) hydroxyl groups, amino groups, mono- or di-C _1-6 alkylamino groups (eg, methylamino, ethylamino, propylamino, dimethylamino, diethylamino, etc.) ), C _1-6 alkoxy groups (eg, methoxy, ethoxy, propoxy, isopropoxy, butoxy, etc.), C _1-6 alkylthio groups (eg, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, etc.), Halogen atom (eg, fluorine, chlorine, bromine, C iodine), a carboxyl group, a nitro group, a cyano group, which may have a phenyl group. When the acyl group is a carbamoyl group, one or two C _1-6 alkyl groups (eg, methyl,
Ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, etc., C _3-9 cycloalkyl group (eg, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.), C _2-6 alkenyl Group (eg, vinyl, allyl, 1-propenyl, 1-butenyl, 2-butenyl, etc.), C _2-6 alkynyl group (eg, ethynyl, 1-propynyl, propargyl, 1-butynyl, etc.), hydroxyl group, C _{1 -6} alkoxy group (eg, methoxy, ethoxy, propoxy, isopropoxy, butoxy, etc.), amino group, mono- or di-C _1-6 alkylamino group (eg, methylamino, ethylamino, propylamino, dimethylamino, Diethylamino, etc.), cyclic amino group (eg, 1-pyrrolidino, piperidino, morpholino, 4-methyl-1-piperazi) Or a phenyl group, and the substituent forms a cyclic amino group (eg, 1-pyrrolidino, piperidino, morpholino, 4-methyl-1-piperazino, etc.) together with the nitrogen atom to which it is bonded. You may. Further, the substituent may be a hydroxyl group, an amino group, a mono- or di-C _1-6 alkylamino group (eg, methylamino, ethylamino, propylamino,
Dimethylamino, diethylamino, etc.), C _1-6 alkoxy group (eg, methoxy, ethoxy, propoxy, isopropoxy, butoxy, etc.), C _1-6 alkylthio group (eg, methylthio, ethylthio, n-propylthio, isopropylthio, n -Butylthio, etc.), 1 to 6 (preferably 1 to 3) substituents selected from a halogen atom (eg, fluorine, chlorine, bromine, iodine), a phenyl group, a carboxyl group, a nitro group and a cyano group. May be. R
^5c is an alkyl group which may be substituted among the above, an alkanoyl group which may be substituted, a cycloalkanoyl group which may be substituted, an alkenylcarbonyl group which may be substituted, and which may be substituted. An arylcarbonyl group, an optionally substituted alkoxycarbonyl group, and an optionally substituted carbamoyl group are preferred. In particular, (1) C _1-6 1 to 3 amino optionally substituted by C _1-6 alkyl group with an alkoxy, (2) C _1-6 alkyl with one or two optionally substituted amino, C _1-6 alkoxy, phenyl or a C _1-10 alkanoyl group optionally substituted with 1 to 3 halogen atoms, (3) C _4-10 cycloalkanoyl group, (4) C _3-10 alkenylcarbonyl group, ( 5) benzoyl group, (6) C _1-6 alkyl _optionally substituted with phenyl, C _3-9 cycloalkyl, C _2-6 alkenyl, C _2-6 alkynyl, phenyl, C _1-6 alkyl Or a carbamoyl group optionally substituted by one or two aminos which may be substituted with two or more amino, cyclic amino, hydroxyl or C _1-6 alkoxy, (7) a cyclic aminocarbonyl group, (8) a C _1-6 Alkoxy-carbonyl or (9) formyl is preferred. As the compound [III], compounds shown in the following Tables 37 to 70 or salts thereof are preferably used.

[0081]

[Table 37]

[0082]

[Table 38]

[0083]

[Table 39]

[0084]

[Table 40]

[0085]

[Table 41]

[0086]

[Table 42]

[0087]

[Table 43]

[0088]

[Table 44]

[0089]

[Table 45]

[0090]

[Table 46]

[0091]

[Table 47]

[0092]

[Table 48]

[0093]

[Table 49]

[0094]

[Table 50]

[0095]

[Table 51]

[0096]

[Table 52]

[0097]

[Table 53]

[0098]

[Table 54]

[0099]

[Table 55]

[0100]

[Table 56]

[0101]

[Table 57]

[0102]

[Table 58]

[0103]

[Table 59]

[0104]

[Table 60]

[0105]

[Table 61]

[0106]

[Table 62]

[0107]

[Table 63]

[0108]

[Table 64]

[0109]

[Table 65]

[0110]

[Table 66]

[0111]

[Table 67]

[0112]

[Table 68]

[0113]

[Table 69]

[0114]

[Table 70]

The salt of the compound [III] of the present invention may be any salt acceptable in agrochemical chemistry. That is, when the molecule has an acidic group such as a carboxyl group or a sulfo group, a salt with a base may be formed. Examples of the base include alkali metals such as sodium, potassium and lithium, calcium and magnesium. And inorganic bases such as ammonia, and organic bases such as pyridine, collidine, triethylamine and triethanolamine. When the molecule has a basic group such as an amino group in the molecule, a salt with an acid may be formed. Examples of the acid include hydrochloric acid, hydrobromic acid, hydroiodic acid, phosphoric acid, Sulfuric acid, salts of inorganic acids such as perchloric acid or for example, formic acid, acetic acid, tartaric acid, malic acid, citric acid,
Salts of organic acids such as oxalic acid, succinic acid, benzoic acid, picric acid, methanesulfonic acid and p-toluenesulfonic acid are used. The compound [III] may form an inner salt, which is also included in the present invention.

The compound [III] of the present invention or a salt thereof, and the compound [IV] used as a raw material for producing the following compound [III] or a salt thereof are described in WO97 / 281.
26 or a method analogous thereto. In general, compound [III] or a salt thereof is synthesized by reacting compound [IV] as a raw material with an acylating agent or an alkylating agent in the presence of an appropriate acid or base catalyst as required. Can be. Examples of the acylating agent used in such a reaction include carboxylic acid halides (eg, acetyl chloride, propionyl bromide, etc.), carbamoyl halides (eg, chloride
N, N-dimethylcarbamoyl, N, N-diethylcarbamoyl chloride, etc.), halogenocarbonate (eg, methyl chlorocarbonate, phenylchlorocarbonate, etc.), dialkyl dicarbonate (eg, di-tert-butyl dicarbonate, dimethyl dicarbonate, etc.) ), Carboxylic anhydride (eg, acetic anhydride, propionic anhydride, etc.)
A publicly known acylating agent such as the above can be used. Examples of the alkylating agent used in such a reaction include alkyl halides (eg, methyl iodide, ethyl bromide, etc.), alkyl sulfonates (eg, methyl methanesulfonate, p-
Ethyl toluenesulfonate, methyl trifluoromethanesulfonate, etc.), dialkyl sulfate (eg, dimethyl sulfate,
Known alkylating agents such as diethyl sulfate and the like, and trialkyl orthoformate (eg, trimethyl orthoformate, triethyl orthoformate and the like) can be used. In this reaction, the amount of the above-mentioned acylating agent or alkylating agent is not particularly limited, and a large excess may be used as a solvent. Examples of the base catalyst used in this reaction include, for example, sodium ethylate, sodium methylate, potassium tert.
Alkoxides of alkali metals such as -butoxide and the like; organic bases such as triethylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, N, N-dimethylaniline and the like, for example, potassium carbonate, sodium carbonate, sodium hydroxide, potassium hydroxide, carbonate Inorganic bases such as sodium hydrogen, potassium bicarbonate, and sodium hydride can be used. The amount of the base to be used is not particularly limited as long as it does not adversely affect the reaction, and a large excess can be used also as a solvent, but is preferably 0.1 to 20 equivalents. Examples of the acid catalyst used in this reaction include, for example, inorganic protic acids such as hydrochloric acid, hydrobromic acid, hydroiodic acid, phosphoric acid, and sulfuric acid, for example, formic acid, acetic acid, tartaric acid, malic acid, citric acid, and oxalic acid And organic protonic acids such as succinic acid, benzoic acid, trifluoroacetic acid and p-toluenesulfonic acid, and Lewis acids such as aluminum chloride, ferric chloride, zinc chloride, titanium tetrachloride and boron trifluoride. The amount of the acid catalyst used in the reaction is not particularly limited as long as it does not adversely affect the reaction, and a large excess can be used as a solvent.
Preferably it is 0.1 to 20 equivalents. This reaction can be performed using a suitable solvent. Such solvents include:
There is no particular limitation as long as it does not give a by-product by reacting with the reaction substrate, the reaction reagent and the product, but it is desirable to dissolve both the reaction substrate and the reaction reagent. Such solvents include, for example, pentane, hexane, heptane,
Aliphatic hydrocarbons such as petroleum ether, aromatic hydrocarbons such as benzene, toluene, xylene, esters such as methyl acetate, ethyl acetate, ethyl formate, ethyl propionate, ketones such as acetone and methyl ethyl ketone, and diethyl ether Ethers such as dipropyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran and dioxane; nitriles such as acetonitrile and propionitrile; acid amides such as dimethylformamide and dimethylacetamide; sulfoxides such as dimethyl sulfoxide; and sulfolane. Sulfones, phosphoric amides such as hexamethylphosphoramide, dichloromethane, chloroform, 1,2-dichloroethane, halogenated hydrocarbons such as carbon tetrachloride, pyridine, picoline,
Aromatic amines such as lutidine and quinoline, a mixed solvent thereof, water, and a mixed solvent of these and water are used.

The reaction temperature is usually about -50 to 200 ° C, and the reaction time is generally about 0.1 to 96 hours. When the compound [III] is obtained as a free compound, it can be converted into a salt as described above, and when obtained as a salt, can be converted into a free compound according to a conventional method. When the compound contained in the compound [III] is used as a raw material for producing another kind of the compound [III], it may be used as it is or as a salt. When other raw materials can be salts as described above, they can be used not only free but also as salts. Therefore, the starting compounds and products used in the following production methods include salts thereof (for example, salts with acids as described in the above compound [III]). Compound [III] or a salt thereof can be specifically produced by the following method.

[Reaction formula (A)]

Embedded image

[Reaction formula (B)]

Embedded image

[Reaction formula (C)]

Embedded image

[Reaction formula (D)]

Embedded image

[Reaction formula (E)]

Embedded image

[Reaction formula (F)]

Embedded image

[Reaction formula (G)]

Embedded image

[Reaction formula (H)]

Embedded image

In the above reaction formulas (A) to (H), X ^c , n ^c ,
R ^1c , R ^4c and R ^5c are as defined above, and R ^5ca is an ^optionally substituted C _1-9 alkyl group, an _optionally substituted C _3-9 cycloalkyl group, Good C
_2-6 alkenyl group, phenyl group which may be substituted,
A C _1-6 alkoxy group, a mono- or di-C _1-6 alkylamino group, R ^5cb is an ^optionally substituted C _1-9 alkyl group, an ^optionally substituted C _3-9 cycloalkyl group, optionally substituted C _2-6 alkenyl group, a phenyl group which may be ^{substituted, R 5cc, R 5cf, R} 5cg is a C _1-6 alkyl group which may be substituted, m ^c is 1 Or 2
The, R ^{5 cd,} R ^5CE a hydrogen atom, an optionally substituted C
_1-6 alkyl group, _optionally substituted C _4-9 cycloalkyl group, _optionally substituted C _2-6 alkenyl group,
_Represents an optionally substituted C _2-6 alkynyl group, an optionally substituted phenyl group, a mono- or di-C _1-6 alkylamino group, a cyclic amino group, a hydroxyl group, a C _1-6 alkoxy group, Or a cyclic amino group together with the nitrogen atom to be bound. ^Examples of the alkyl group of the ^optionally substituted C _1-9 alkyl group for R ^5ca and R ^5cb include, for example, methyl, ethyl, n-propyl, isopropyl,
n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, neo-pentyl, 1-ethylpropyl,
Examples include 1-propylbutyl, n-hexyl, n-heptyl, n-octyl, n-nonyl and the like. Examples of the substituent for the alkyl group include the same substituents as those described above for the ^optionally substituted alkyl group for R ^5c . The number of substitutions is 1 to 6, preferably 1 to 3 within the range where substitution is possible. ^{R 5cc, R 5cd, R 5ce} , R 5cf, R
^{As the optionally} substituted C _1-6 alkyl group for ^5cg, the same as the ^{aforementioned optionally} substituted alkyl group for R ^5c can be mentioned. ^{R 5ca, R 5cb, R 5cd} , R
^As the substituent for the phenyl group of ^5ce , the same substituents as those for the acyl group (arylcarbonyl group) in R ^5c can be mentioned. The number of substituents is 1-5 (preferably 1-
3). R ^5ca, R ^{5 cd,} as the C _1-6 alkoxy group in R ^5CE methoxy, ethoxy, propoxy,
Isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy and the like. R ^5ca , R ^5cd ,
As the C _1-6 alkyl of the mono- or di -C _1-6 alkylamino group R ^5CE include the same alkyl groups exemplified above for R ^{1. R 5ca, R 5cb, R 5cd} ,
^Examples of the cycloalkyl group of the ^optionally substituted C _3-9 cycloalkyl group for R ^5ce include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like. ^{R 5ca, R 5cb, R 5cd} , vinyl for example, the alkenyl group optionally C _2-6 alkenyl group which may be substituted in R ^5CE, allyl, 1-propenyl, 1-
Butenyl, 2-butenyl and the like. ^{R 5cd,} R 5ce
Examples of the alkynyl group of the optionally substituted C _2-6 alkynyl group include, for example, ethynyl, 1-propynyl,
And propargyl and 1-butynyl. R ^5cd ,
^Examples of the cyclic amino group for R ^5ce include 1-pyrrolidino, piperidino, morpholino, 4-methyl-1-piperazino and the like. The cycloalkyl group, alkenyl group, alkynyl group, and cyclic amino group described above are a hydroxyl group, an amino group, a mono- or di-C _1-6 alkylamino group (eg, methylamino, ethylamino, propylamino, dimethylamino , Diethylamino, etc.), C
_{A 1-6} alkoxy group (eg, methoxy, ethoxy, propoxy, isopropoxy, butoxy, etc.), a C _1-6 alkylthio group (eg, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, etc.), a halogen atom ( E.g., fluorine, chlorine, bromine, iodine), phenyl group,
It may be substituted with 1 to 6 (preferably 1 to 3) substituents selected from a carboxyl group, a nitro group and a cyano group. Also, R ^{5 cd,} as the cyclic amino group together with the nitrogen atom to which R ^5CE are attached, such as 1-pyrrolidino, piperidino, morpholino, 4-methyl-1-piperazino and the like.

The reaction formula (A) shows that the compound [IV] can be ^converted to R ^5ca C
OL ^c [L ^c is a halogen atom (eg, fluorine, chlorine, bromine,
Iodine), acyloxy group (C _1-6 alkyl-carbonyloxy group _optionally substituted by 1 to 3 halogen atoms such as acetoxy group, propionyloxy group and trifluoroacetoxy group; methoxycarbonyloxy, t-butoxycarbonyloxy shows a C _1-10 acyloxy group such as a carbonyl group) leaving group such as - C _1-6 alkoxy, such as. The reaction of producing a compound [V] by reacting with an acylating agent represented by the formula Compound [IV] not only serves as a raw material for this reaction, but also has excellent insecticidal activity. Preferred examples of compound [IV] include, for example, 1-
(2,6-dichloro-4-trifluoromethylphenyl) -5-ethoxymethyleneamino -3- (Δ ² -1,
2,4-oxadiazolin-3-yl) -4-trifluoromethylsulfinylpyrazole, 1- (2,6-dichloro-4-trifluoromethylphenyl) -3- (Δ
² -1,2,4-oxadiazolin-3-yl) -5-
(N-propoxymethyleneamino) -4-trifluoromethylthiopyrazole, 1- (2,6-dichloro-4-
Trifluoromethylphenyl) -3- (Δ ² -1,2,
4-oxadiazolin-3-yl) -5- (n-propoxymethyleneamino) -4-trifluoromethylsulfonylpyrazole. These compounds can also be advantageously used in the method of the present invention. In this reaction, the amount of the above-mentioned acylating agent is not particularly limited, and a large excess may be used as a solvent, but it is preferably about 0.8 to 5 equivalents. For the purpose of accelerating the reaction and reducing by-products, good results may be obtained by coexisting with a base or acting before and after the reaction. Such bases include, for example, sodium ethylate,
Alcoholates of alkali metals such as sodium methylate and potassium tert-butoxide, for example, organic bases such as triethylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine and N, N-dimethylaniline, for example, potassium carbonate, sodium carbonate, sodium hydroxide , Potassium hydroxide, sodium bicarbonate, potassium bicarbonate, sodium hydride and the like. The amount of the base used is not particularly limited as long as it does not adversely affect the reaction, and a large excess can be used also as a solvent. This reaction can be performed using a suitable solvent. The solvent is not particularly limited as long as it does not give a by-product by reacting with the reaction substrate, the reaction reagent and the product, but a solvent that dissolves both the reaction substrate and the reaction reagent is desirable. Examples of such a solvent include aliphatic hydrocarbons such as pentane, hexane, heptane and petroleum ether, aromatic hydrocarbons such as benzene, toluene and xylene, and esters such as methyl acetate, ethyl acetate, ethyl formate and ethyl propionate. , Acetone, ketones such as methyl ethyl ketone, ethers such as diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran and dioxane; nitriles such as acetonitrile and propionitrile; acid amides such as dimethylformamide and dimethylacetamide , Sulfoxides such as dimethyl sulfoxide, sulfones such as sulfolane, phosphoric amides such as hexamethylphosphoramide, and halogenated compounds such as dichloromethane, chloroform, 1,2-dichloroethane and carbon tetrachloride. Gen hydrocarbons, pyridine, picoline, lutidine,
Aromatic amines such as quinoline, a mixed solvent thereof, water, and a mixed solvent of these and water are used. The reaction temperature is generally about -50 to 200C, preferably about -30 to 150C. The reaction time is generally about 0.1-96 hours, preferably 0.1-72 hours, more preferably about 0.1-24 hours. The obtained compound is separated and purified by a method known per se, for example, concentration, concentration under reduced pressure, liquid conversion, phase transfer, solvent extraction, distillation, crystallization, recrystallization, chromatography, etc. May be used as a raw material for the reaction described above.

The reaction formula (B) shows that the compound [IV] is ^{prepared by converting} R ^5cb C
O ₂ H [R ^5cb is as defined above. The reaction of producing a compound [VI] by reacting a carboxylic acid derivative represented by the formula [1] with a dehydrating condensing agent is shown. As the dehydrating condensing agent used in this reaction, a known dehydrating condensing agent such as DCC (dicyclohexylcarbodiimide), carbonyldiimidazole, BOP reagent (benzotriazol-1-yloxy-tris (dimethylamino) phosphonium hexafluorophosphate) is used. Can be The amount used is not particularly limited, but is preferably 0.8 to 5 equivalents. The amount of the carboxylic acid derivative used in this reaction is not particularly limited, and a large excess can be used as a solvent.
Is equivalent.

In the reaction formula (C), the compound [IV] is ^converted to R ^5cc NC
O [R ^5cc is as defined above. The reaction for producing a compound [VII] by reacting with an isocyanate derivative represented by the formula The amount of the isocyanate derivative used in this reaction is not particularly limited, and a large excess may be used as a solvent, but is preferably about 0.8 to 5 equivalents. For the purpose of accelerating the reaction and reducing by-products, good results may be obtained by coexisting with a base or acting before and after the reaction. The type and amount of the base used are
The same as the reaction formula (A).

[0130] Reaction formula (D) is by reacting the compound (IV) with phosgene or an equivalent thereof, and the intermediate [VIII], this ^{R 5cd} R 5ce NH [R ^{5 cd,} R ^5CE is as defined above Show. The compound represented by the formula (IX)
Shows the reaction for producing Phosgene, trichloromethyl chloroformate (diphosgene), bistrichloromethyl carbonate (triphosgene) and the like are used as phosgene or its equivalent used in this reaction. The amount used is not particularly limited, but is preferably from 0.3 to 5 equivalents. Intermediate [VIII] is separated by a means known per se, for example, concentration, concentration under reduced pressure, liquid conversion, phase transfer, solvent extraction, distillation, crystallization, recrystallization, chromatography, etc., after purification, or as a reaction mixture. It may be used as a raw material for the next reaction. The amount of amine represented by ^{R 5cd} R 5ce NH used in this reaction is not particularly limited, but can be used in large excess as the solvent is generally about 0.8 to 5 equivalents.

In the reaction formula (E), the compound [IV] is ^converted to R ^5cf Hal
[ ^Wherein , R ^5cf has the same meaning as described above, and Hal represents a halogen atom (eg, fluorine, chlorine, bromine, iodine). With an alkyl halide represented by the formula (X)
Shows the reaction for producing R ^5cf Ha used in this reaction
The amount of the alkyl halide represented by 1 is not particularly limited, and a large excess can be used as a solvent, but it is usually about 0.8 to 5 equivalents. For the purpose of accelerating the reaction and reducing by-products, good results may be obtained by coexisting with a base or acting before and after the reaction. The kind and amount of the base are the same as those in the reaction formula (A).

In the reaction formula (F), the compound [XI] is reacted with formaldehyde or an equivalent thereof to give the compound [XII]
Shows the reaction for producing Formaldehyde or its equivalent used in this reaction includes formaldehyde,
Paraformaldehyde and the like are used. The amount to be used is not particularly limited, and a large excess can be used as a solvent, but the amount is preferably 0.8 to 15 equivalents. For the purpose of accelerating the reaction and reducing by-products, good results may be obtained by coexisting with an acid or acting before and after the reaction. Such acid catalysts include, for example,
Inorganic protic acids such as hydrochloric acid, hydrobromic acid, hydroiodic acid, phosphoric acid, sulfuric acid and the like, for example, formic acid, acetic acid, tartaric acid, malic acid, citric acid, oxalic acid, succinic acid, benzoic acid, trifluoroacetic acid, p -Organic protonic acids such as toluenesulfonic acid, and Lewis acids such as aluminum chloride, ferric chloride, zinc chloride, titanium tetrachloride, boron trifluoride and the like are used. The amount of the acid catalyst used in the reaction is not particularly limited as long as it does not adversely affect the reaction, and a large excess can be used as a solvent.

The reaction formula (G) shows a reaction for producing the compound [XIV] by oxidizing the compound [XIII] with an oxidizing agent.
As the oxidizing agent used in this reaction, for example, hydrogen peroxide, peracetic acid, perbenzoic acid, m-chloroperbenzoic acid, sodium metaperiodate, ozone, selenium dioxide, chromic acid, bromine, N-bromosuccinimide And an oxidizing agent such as iodosylbenzene and t-butyl hypochlorite. The amount to be used is not particularly limited, and a large excess can be used as a solvent, but the amount is preferably 0.8 to 5 equivalents.

In the reaction formula [H], the compound [XV] is converted to CH (OR
^4c ) The reaction of reacting with a trialkyl orthoformate represented by ₃ to produce a compound [XVI]. The amount of the trialkyl orthoformate used in this reaction is not particularly limited, and a large excess can be used as a solvent, but it is preferably 0.8 to 15 equivalents. For the purpose of accelerating the reaction and reducing by-products, good results may be obtained by coexisting with an acid or acting before and after the reaction. Such acid catalysts include, for example, inorganic protic acids such as hydrochloric acid, hydrobromic acid, hydroiodic acid, phosphoric acid, and sulfuric acid, for example, formic acid, acetic acid, tartaric acid, malic acid, citric acid, oxalic acid, succinic acid, Organic protonic acids such as benzoic acid, trifluoroacetic acid, p-toluenesulfonic acid, aluminum chloride, ferric chloride, zinc chloride,
Lewis acids such as titanium tetrachloride and boron trifluoride are used. The amount of the acid catalyst used in the reaction is not particularly limited as long as it does not adversely affect the reaction, and a large excess can be used as a solvent.

Each of the reactions of the reaction formulas (B) to (H) can be carried out using a suitable solvent. Such solvents include:
The same one as described above in the reaction formula (A) is used. The temperature used for each reaction of the reaction formulas (B) to (H) is usually about -50 to 200C, preferably about -200C.
30-150 ° C. The reaction time is generally about 0.1 to
96 hours, preferably about 0.1 to 72 hours, more preferably about 0.1 to 24 hours. Reaction formulas (B) to (H)
The compound obtained in each of the above reactions may be separated and purified by a means known per se described in the reaction formula (A), or may be used as a reaction mixture as a starting material for the next reaction. Agrochemical compositions containing the above-mentioned compounds [I], [II] and [III] or salts thereof have excellent insecticidal activity, are extremely toxic, are safe, and are excellent as pesticide compositions (pesticides). Can be used.

[0136]

DESCRIPTION OF THE PREFERRED EMBODIMENTS In using an agricultural chemical active ingredient effective for controlling sanitary pests and plant parasitic insects, a form which can be taken by a general agricultural chemical, one or more agricultural chemical active ingredients by themselves or Emulsions, liquids, microemulsions, flowables, oils, aqueous solvents, wettable powders, powders, granules, fine granules, dissolved or dispersed in a suitable liquid carrier, or mixed or adsorbed with a suitable solid carrier , Microcapsules and the like. If necessary, these preparations may contain, for example, an emulsifier, a suspending agent, a spreading agent, a penetrant, a wetting agent, a mucilage, a stabilizer and the like, and can be prepared by a method known per se.

Examples of the liquid carrier (solvent) used include water, alcohols (eg, methyl alcohol, ethyl alcohol, n-propyl alcohol, isopropyl alcohol, ethylene glycol, etc.), ketones (eg, acetone, methyl ethyl ketone, etc.), ethers (Eg, dioxane, tetrahydrofuran, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, etc.), aliphatic hydrocarbons (eg, kerosene, kerosene, fuel oil, machine oil, etc.), and aromatic hydrocarbons (eg, benzene) ,
Toluene, xylene, solvent naphtha, methyl naphthalene, etc.), halogenated hydrocarbons (eg, dichloromethane, chloroform, carbon tetrachloride, etc.), acid amides (eg, N, N-dimethylformamide, N, N-dimethylacetamide, etc.), Solvents such as esters (eg, ethyl acetate, butyl acetate, fatty acid glycerin ester, etc.) and nitriles (eg, acetonitrile, propionitrile, etc.) are suitable, and these may be used alone or in a mixture of two or more at an appropriate ratio. It can be used as appropriate. Solid carrier (diluted
Examples of the bulking agent include vegetable powders (eg, soybean powder, tobacco powder, flour, wood flour, etc.) and mineral powders (eg, kaolin,
Clays such as bentonite and acid clay, talc such as talc powder and lauric powder, silicas such as diatomaceous earth and mica powder), alumina, sulfur powder, activated carbon and the like are used, and one or more of these are suitable. It can be used by mixing at an appropriate ratio.

Surfactants used as emulsifiers, spreading agents, penetrants, dispersants and the like include soaps,
Polyoxyethylene alkyl aryl ethers (e.g.,
Neugen (trade name), E-A142 (trade name); manufactured by Daiichi Kogyo Seiyaku Co., Ltd., Nonal (trade name);
Toho Chemical Co., Ltd.], alkyl sulfates [eg, Emar 10 (trade name), Emar 40 (trade name); Kao Corporation
Manufactured by Daiichi Kogyo Seiyaku Co., Ltd.), alkyl sulfonates [eg, Neogen (trade name), Neogen T (trade name);
Neoperex; manufactured by Kao Corporation], alkyl sulfosuccinate salts (eg, Newcalgen EP-60P (manufactured by Takemoto Yushi Co., Ltd.)), polyethylene glycol ethers (eg, Nonipol 85 (trade name), Nonipol 100
(Trade name), Nonipol 160 (trade name); manufactured by Sanyo Chemical Co., Ltd.), polyhydric alcohol esters [eg, Tween 20 (trade name), Tween 80 (trade name); manufactured by Kao Corporation], etc. Nonionic and anionic surfactants are used as appropriate. Further, the above-mentioned preparations may be used, if necessary, with sodium salts of carboxymethylcellulose (eg, cellogen 6A, cellogen 7A (Daiichi Kogyo Seiyaku Co., Ltd.)) and dextrin (eg, dextrin ND-S (Nichise Chemical Co., Ltd.)) And the like. Compounds (I) and (I
I], [III] or a salt thereof and, for example, other kinds of insecticides (pyrethroid insecticides, organophosphate insecticides, carbamate insecticides, neonicotinoid insecticides, natural insecticides, etc.), acaricides , Nematicides, herbicides, phytohormones,
Formulated with plant growth regulators, fungicides (eg, copper fungicides, organochlorine fungicides, organosulfur fungicides, phenolic fungicides, etc.), synergists, attractants, repellents, pigments, fertilizers, etc. However, it can be used as appropriate.

When the pesticidal active ingredient is used as a composition, the content of the pesticidal active ingredient in the composition depends on the kind of the pesticide active ingredient, but is usually about 0.1 to 80% by weight, preferably about 0.5% by weight. -20% by weight. For example, when the compound [I], [II], [III] or a salt thereof is used as the pesticidal active ingredient, the compound [I], [I
The content of [I], [III] or a salt thereof is usually about 0.1 to 80% by weight, preferably about 0.1 to 80% by weight, based on the total amount of the composition.
It is about 5 to 20% by weight. Specifically, emulsions, solutions,
When used in water solvents, wettable powders, etc., usually about 0.1 to 8
About 0% by weight, preferably about 1 to 50% by weight is suitable. When used in oils, powders, etc., usually about 0.1
About 50% by weight, preferably about 0.1-20% by weight. When used in granules, etc., usually about 5
About 50% by weight, preferably about 1 to 20% by weight is appropriate. Other pesticidal active ingredients (eg, insecticides, herbicides, acaricides and / or fungicides) that can be compounded in addition to the compounds [I], [II], [III] or salts thereof described below are included in the total amount of the preparation. On the other hand, it is usually used in the range of about 1 to 80% by weight, preferably about 1 to 20% by weight. The content of the additives other than the above-mentioned active ingredients varies depending on the kind or content of the pesticidal active ingredient or the dosage form of the preparation, but is usually about 0.001 to 99.9% by weight, preferably about 1 to 9% by weight.
It is about 9% by weight. More specifically, the surfactant is usually about 1 to 20% by weight, preferably about 1 to 15% by weight, the flow aid is about 1 to 20% by weight, and the carrier is about 1 to 20% by weight based on the total amount of the composition. It is preferred to add 1 to 90% by weight, preferably about 1 to 70% by weight. Specifically, in the case of producing a liquid preparation, the surfactant is usually about 1 to 20% by weight,
Preferably, about 1 to 10% by weight and about 20 to 90% by weight of water are added. Emulsions, aqueous solvents, wettable powders, etc. are diluted appropriately with water or the like when used (for example, about 1
(00 to 5,000 times).

Compounds [I], [II] and [III] of the present invention
Or pesticides, acaricides that can be used in combination with their salts,
Representative examples of the bactericide are shown below. EPN (EPN), acephate, isoxathion,
Isofenphos, isoprocarb (isop)
rocarb), etrimfos, oxydeprofos, quinalphos, cadusafos, chlorethoxyphos
hoxyfos), chlorpyrifos, chlorpyrifos-methyl, chlorofenvinphos, salithion
thion), cyanophos (cyanophos), disulfoton (di
sulfoton), dimethoate, sulprofos, diazinon, thiometon, tetrachlorovinphos (tetrachlo)
rvinphos), tebupirimfos, trichlorphon, naled, vamidothion, pyraclopho
s), pyridafenthion, pyrimiphos-methyl, fenitrothion, fenthion, phenthoate, fosthiazate
azate), butathiofos, prothiofos, propaphos, propenofos, phosalone, phosalone, fosthiazate, malathion,
Methidathion, metolcarb (metolc)
arb), monocrotophos, BPMC
(BPMC), XMC (XMC), alanicarb (alanycar)
b), ethiofencarb, carbaryl, carbosulfan,
Carbofuran (carbofuran), xylylcarb (xylylc)
arb), cloethocarb, thiodicarb, triazemate, pirimicarb, phenoxyca
rb), fenothiocarb, furathiocarb, propoxur, bendiocarb, benfuracarb
uracarb), methomil (methomyl), acrinatrine (a
crinathrin), imiprothrin, ethofenprox, cycloprothrin, sigma-cypermethrin (sigma)
-cypermethrin), cyhalothrin (cyhalothrin), cyfluthrin (cyfluthrin), cypermethrin (cypermethr
in), silafluofen, tefluthrin, deltamethrin,

[0141] Tralomethrin, fenvalerate, fenpropatrin (fen
propathrin), flucythrinate,
Fluvalinate, Flufenoprox, Fluproxyfe
n), flumethrin, praletrin (pra)
llethrin), beta-cyfluthri
n), benfluthrin, permethrin, acetamiprid, imidacloprid, cartap
p), thiocyclam, nitempiram (nit
enpyram), bensultap, avermectin, emamectin benzoate (emam)
ectin-benzoate, clofentezin
e), chlorfluazuron, cyromazine, diafenthiuron
ron), dienochlor, dichlorvos (d
ichlorvos), diflubenzuron, spinosyn (spynosyn), sulfuramid
d), teflubenzuron (teflubenzuron), tebufenozide (tebufenozide), tebufenpyrad (tebufenpyr)
ad), hydroprene, vaniliprole, pymetrozine, pyridaben, pyriproxyne
fen), pyrimidifen, fipronil, fenazaquin, fenpyroximate, fluazuron (flu
azuron), flucycloxuron, flufenoxuron, buprofezin, hexaflumuron,
Hexythiazox, milbemycin, methoxadiazon
e), lufenuron, levamisole (leva)
misol), chlorfenapyr, NC-1
84 (NC-184), YI-5301 (YI-5301),

[0142] IBP (IBP), ampropylphos (ampro)
pylfos), edifenphos, chlorthiophos, tolclofos-methyl (tolcl
ofos-methyl), fosetyl (fosetyl), ipconazole (ipconazole), imazalil (imazalil), imibenconazole (imibenconazole), etaconazole (etacon)
azole), epoxyconazole (epoxiconazole), cyproconazole (cyproconazole), diniconazole (din
iconazole), difenoconazol
e), tetraconazole, tebuconazole, triadimeno
l), triadimefon, triticonazole, triforine, bitertanol, viniconazole
nazole), fenarimol, fenbuconazole, fluotrimazole (fluot
rimazole), furconazole-cis
s), flusilazole, flutriafol, bromuconazol
e), propiconazole, hexaconazole, pefurazoat
e), penconazole, microbutanil, metconazole,
Carbendazin, debacar
b), prothiocarb, benomyl
myl), maneb, TPN (TPN), isoprothiolane, iprodione (iprodion)
e), iminoctadine-albesil, iminoctadine-triacetate, ethirimol, ethiridiazole (etridiazol)
e), oxadixyl, oxycarboxin, oxolinic aci
d), offurace, kasugamycin (kasuga)
mycin), carboxin (carboxin), captan (cap
tan), clozylacon, chlobenthiazone, cyprodinil (cyprodini)
l), cyprofuram, dietofencarb, dichlofluan
id),

Diclomezine, zineb (z
ineb), dimethirimol, dimethomorph, dimefluazol
e), thiabendazole, thiophenate-methyl, thifluzamide, tecloftalam,
Triazoxide, triclamide
mide), tricyclazole, tridemorph, triflumizol
e), validamycin A, hymexazol, pyracarbolid
d), pyrazophos, pyrifenox (p
yrifenox), pyrimethanil, pyroquilon, ferimzone, fenpiclonil, fenpropidine
propidin), fenpropimorph,
Fthalide, furametpy
r), furalaxyl, fluazinam (flua
zinam), furcarbanil, fluquinconazole, fludioxonil (flu
dioxonil), Flusulfamide, Flutolanil, Butiobat
e), prochloraz (prochloraz), procymidone (pro
cymidone), probenazole (probenazole), benalaxyl (benalaxyl), benodanil (benodanil), pencyclone (pencycuron), microzoline (myclozoli)
n), metalaxyl, metsulfovax, methfuroxam, mepanipyrim, meproni
l), BAS-490F (kresoxim), azoxystrobin, SSF-126 (SSF-126),
Carpropamid

As the pesticidal active ingredient, for example, sea turtle (Eur
ydema rugosum), Rabbit bug (Riptortus clavatu)
s), Nashigumbai (Stephanitis nashi), soybean aphid (Aphis glycines), squash aphid (Lipap
his erysimi), radish aphids (Brevicorynebrassi)
cae), cotton aphid (Aphis gossypii), peach peach aphid (Myzus persicae), potato beetle aphid (Aulacorthum solani), tobacco whitefly (Bemisia t
abaci), whitefly (Trialeurodes vaporarior)
um), brown planthopper (Sogatella furcifera), Hemiptera pests such as the stink bug (Plautia stali), for example, Spodoptera litura, and diamondback moth (Plutella x
ylostella), Pieris rapae crucivor
a), Eelgrass (Autographa nigrisigna), Tobacco moth (Helicoverpa assulta), Armyworm (Pseudaletia)
separata), armyworm (Mamestra brassicae), cotton moth (Notarcha derogata), potato moth (Phthorimaeao)
perculella), Spodoptera exigu (Spodoptera exigu)
a), Kabulaya (Agrotis segetum), Tamanayaga (Agroti
sipsilon), tobacco budworm (Heliothis armigera), tobacco badworm (Heliothis virescens), ball worm
(Heliothis zea), European corn borer (Ostrin
ia nubilalis), Awaneniga (Ostrinia furnacalis),
Lepidopteran pests such as the rice beetle (Parnara guttata), for example, Epilachna vigintioctopunc
tata), beetle beetle (Aulacophorafemoralis), flea beetle beetle (Phyllotreta striolata), cotton beetle (An
thonomus grandis), adzuki beetle (Callosobruchus c
hinensis), Bean beetle (Popillia japonica), Douganebubui (Anomala cuprea), a member of the corn rootworm
(Diabrotica spp.), Colorado potato beetle (Leptinotarsa dec
emlineata), a member of the click beetle (Agriotes spp.), a tobacco beetle (Lasioderma serricorne), a beetle beetle (Anthrenusverbasci), and a beetle
(Tribolium castaneum), Flycatcher beetle (Lyctus bru)
nneus) and other beetles such as onions (Delia ant
iqua), seed fly (Delia platura),
iriomyza trifolii), Nasamoa fly (Liriomyza bry)
oniae) and other dipteran pests, e.g., Locusta
Orthopterous pests such as migratoria), Kera (Gryllotalpa africana), etc. Hymenoptera pests such as, for example, spider mite (Tetranychus urticae), mandarin spider mite (Pa
nonychus citri), Kanzawa spider mite (Tetranychus kanzaw)
ai), spider mite (Tetranychus cinnabarinus), apple spider mite (Panonychus ulmi), citrus mite (Aculop
s pelekassi), Dermatophagoid mites (Polyphagotarsonemus)
latus), spider mites (Rhizoglyphus echinopus) and other pests such as sweet potato nematodes (Meloidogyne
incognita), Pterylenchus p
enetrans), Strawberry nematode (Nothotylenchus acri)
Those effective for controlling nematodes such as s) are used. Compounds [I], [II], [III] or salts thereof include, among the above-mentioned pests, aphids such as cotton aphids and peach aphids, whiteflies such as tobacco whitefly and whitefly, and thrips such as Thrips palmi. It is effective against Lepidoptera, such as Lepidoptera cricket, and Lepidoptera, such as diamondback moth and whitefinch.

The amount of the chemical to be treated can be changed as appropriate depending on the type of the target crop, the size of the container for raising seedlings (eg, box, seedling pot, tray, pot, planter) and the type of pest to be controlled. Generally, the pesticidal active ingredient is 0.005 g to 1.0 g / liter, preferably 0.02 to 0.5 g in terms of the active ingredient.
It may be mixed with the soil at a rate of g / liter before sowing or provisional planting, and the soil mixed with the pesticidal active ingredient may be used as a culture medium for raising seedlings. The pesticidal active ingredient can be mixed with the soil as it is or as a composition, but the wettable powder, the aqueous solvent, and the emulsion may be further diluted with water and mixed with the soil in a solution state. The mixing of the pesticidal active ingredient or its composition with soil may be carried out using a mixer such as a mixer or by manual mixing so that the medicament and the seedling cultivation are uniform. The soil to be used as a seedling cultivation soil to be mixed with a chemical can be used as long as it has good water retention, drainage and air permeability and is suitable for growing crop seedlings. In particular,
Cultivation of seedlings for plug seedlings of all farming, seedlings for cell seedlings, Genki-kun Cell 100 or Nippi Yoshina, soil for Kubotacell seedlings of Kubota Co., Ltd., Mother soil or Sansan floor soil of Takii Seed Co., Ltd., Sumirin Commercially available cultivated soil such as Dotaro of Agricultural Industry Co., Ltd. or mountain soil can be used, but the soil is not limited to the soil described above. In such soil, fertilizers (eg, chemical fertilizer, humus, cow dung, chicken dung, pig dung, etc.), water retention materials (eg, peat moss, humus, vermiculite, etc.) and fertilizers (eg, (Zeolite) and the like. Further, in order to adjust the pH to a suitable level according to the type of crop to be raised, a pH adjuster such as lime or sulfur may be further mixed. Seeding can be done in the usual way,
For example, a resin tray having a size of about 28 cm × about 54 cm, called a cell tray or plug tray, in which about 50 to about 800 small pots are continuously formed, or a poly plastic having a diameter of about 4 cm to about 15 cm, is prepared. It is sufficient to fill a seedling container such as a pot, sow one to several crop seeds per pot, and irrigate after covering the soil. In raising seedlings of crops, the seedlings may be replanted into larger pots during the raising period, and the raising of seedlings may be continued. Even during replanting to such a large pot, that is, during temporary planting, the above-mentioned agent can be mixed with the seedling cultivation soil before the temporary planting, and seedlings can be grown using the seedling cultivation soil mixed with the drug. Raising seedlings is an important task for farmers, and it is no exaggeration to say that the quality of seedlings determines the quality of subsequent crop growth. For this reason, farmers often take a lot of time in planting greenhouses and other facilities from planting seedlings to planting seedlings in a field (constant planting), and carefully perform pest management, water management, temperature management, fertilization management, and the like. In the method of the present invention, the seedlings can be applied in any place suitable for the seedlings, such as in a facility or an open field. The seedling raising period is generally one week to three months, depending on the target crop. The temperature suitable for raising seedlings depends on the target crop, but is generally about 0 ° C to about 50 ° C, preferably about 10 ° C to about 30 ° C.
° C. According to the method of the present invention,
Even when pest control is required only during the seedling raising period, spraying during the seedling raising period can be omitted only by treating a small amount of the pesticide active ingredient once, which is excellent in economy. Further, according to the present invention, it is possible to separate the control chemical treatment operation from the planting operation, and avoid busy busy planting, so that the agent can be mixed with the soil as an operation during the off-farm season. The period from mixing to use depends on the type of soil, humidity, etc., but in dry soils, mixing may be performed at a time more than one month before the farmer's convenience. In addition, the above-mentioned materials such as fertilizers, pH regulators, and water retention improvers are usually mixed into the cultivation for seedling raising, but the chemicals can be mixed with the soil at the same time, and the labor required for the chemical treatment in the present invention. Is very small. In addition, since pests are controlled by bringing in chemicals by cultivation for raising seedlings, planting of crop seedlings in fields (eg, facilities such as greenhouses, open fields, etc.) requires manual or conventional machines (eg, transplanting machines). ) May be used.

The crops to be used in the present invention are angiosperms other than rice (eg, poppy-order, red-eye-order, rose-order, cell-order), which are planted in a nursery container such as a plastic pot or a cell tray and then planted in this field. Or dicotyledonous plants such as Lepidoptera, Plants such as Camellia or Malvaceae or joint plants such as Lamies, Cucurbites, Psychospermaceae, Psocoptera, Pteridophytes or Primroses, Lilies and Poaceae (however, And monocots such as plants). Poppy plants include Chinese cabbage, cabbage, cauliflower, broccoli,
Examples include cruciferous plants such as stocks. Examples of the Rhododendron plants include a Rhododendron plant such as spinach and a carabididae plant such as carnation. Rosaceae plants include legumes such as snow peas, lozenges and green beans, and roses such as strawberries.
As the Aceraceous plants, there may be mentioned Umbelliferae plants such as parsley and celery. Vampire plants such as pansies are mentioned as the Camellia plants. Examples of the mallow plants include mallow plants such as okra. The Lamiaceae plants include solanaceous plants such as eggplant, tomato, tobacco, and peppers, and Lamiaceae plants such as salvia. Cucurbits, cucumber, pumpkin, watermelon, melon, and other cucurbits are examples of the Cucurbitaceae plants. Asteraceae plants include Asteraceae plants such as lettuce, chrysanthemum, chrysanthemum and marigold. Isopodaceous plants include Isopine family plants such as starches. Examples of the Oleaceae plants include gentian plants such as eustoma. Primrose plants include primroses such as cyclamen. Lily plants include lily plants such as leek and onion. Gramineae plants include grassy plants such as sweet corn. A flow chart of the cultivation procedure of the crop is shown in FIG.

[0147]

EXAMPLES The present invention will be described more specifically with reference to Reference Examples and Test Examples, which should not be construed as limiting the present invention. Elution in column chromatography of the reference example was performed using TLC (Thin Layer Chromatogra
phy, thin layer chromatography). In the TLC observation, a Kieselgel 60F254 (70 to 70) manufactured by Merck was used as a TLC plate.
230 mesh), a solvent used as an elution solvent in column chromatography as a developing solvent, and a UV detector as a detection method. As the silica gel for the column, Kieselgel 60 (70-230 mesh) also manufactured by Merck was used. The NMR spectrum shows proton NMR, which was measured with a Bruker AC-200P (200 MHz) spectrometer using tetramethylsilane as an internal standard, and all δ values were shown in ppm. When a mixed solvent is used as a developing solvent, the numerical values shown in parentheses indicate the volume mixing ratio of each solvent. The abbreviations in the present specification have the following meanings. Me: methyl group, Et: ethyl group, Ph:
Phenyl group, Pr-n (or n-Pr): n-propyl, Pr-i (or i-Pr): isopropyl, B
un (or n-Bu): n-butyl, Bu-i (or i-Bu): isobutyl, Bu-s (or s)
-Bu): sec-butyl, Bu-t (or t-B)
u): tert-butyl, s: singlet, br: broad (broad), brs: broad singlet (broad singlet), d: doublet, t: triplet,
q: quartet, qu: quintet (quintuple),
m: multiplet, dd: double doublet, dt:
Double triplet, J: coupling constant, Hz: hertz,%: weight%, mp: melting point, and room temperature is about 1
Mean 5-25 ° C.

[0148]

Reference Example 1 1- (2,6-dichloro-4-trifluoromethylphenyl) -5-ethoxymethyleneamino-3
- (Δ ² -1,2,4- oxadiazolin-3-yl)
-4-trifluoromethylsulfinylpyrazole 5-amino-1- (2,6-dichloro-4-trifluoromethylphenyl) -3- (Δ ² -1,2,4-oxadiazolin-3-yl)- 31.6 g (65.4 mmol) of 4-trifluoromethylsulfinylpyrazole is dissolved in 315 ml (1.89 mmol) of triethyl orthoformate, 1.25 g (6.54 mmol) of p-toluenesulfonic acid monohydrate is added, and the mixture is stirred at 40 ° C for 4 hours. did. After the reaction, triethyl orthoformate was distilled off under reduced pressure, n-hexane and a small amount of chloroform were added to the residue, and the mixture was thoroughly rubbed. The resulting crystals were collected by filtration, dried, and dried.
g (14.8 mmol) of 1- (2,6-dichloro-4-trifluoromethylphenyl) -5-ethoxymethyleneamino-3- (Δ ² -1,2,4-oxadiazolin-3-yl)- 4-trifluoromethylsulfinylpyrazole was obtained as colorless crystals. After concentrating the filtrate, acetonitrile
200 ml and 50 ml of water were added, 0.5 ml of 1.2 N hydrochloric acid was added, and the mixture was allowed to stand at room temperature for 30 minutes. After concentration under reduced pressure, a mixed solvent of n-hexane-acetone was added and the mixture was rubbed well. The resulting crystals were collected by filtration, dried, and further treated with 21.1 g (39.2 mmol) of 1- (2,6-dichloro-4-trifluoromethylphenyl). ) -5-ethoxymethyleneamino-3- (delta ^{2-1,2,4-oxadiazolin-3-yl)} -4-trifluoromethyl sulfinyl pyrazole. 82% yield. mp. 186-187 ° C NMR (CDCl ₃ , δ) 1.20 (3H, t, J = 7Hz), 4.08 (2H, m), 5.21
(1H, br), 5.44 (1H, s), 5.49 (1H, s), 7.75 (1H, s),
7.76 (1H, s), 8.50 (1H, br)

Using the same method, the following compounds were synthesized. 1- (2,6-dichloro-4-trifluoromethylphenyl) -3- (delta ^{2-1,2,4-oxadiazolin-3-yl)-5-(n-propoxy} methylene) -4- Trifluoromethylthiopyrazole mp. 106
~ 107 ℃

1- (2,6-dichloro-4-trifluoromethylphenyl) -3- (Δ ² -1,2,4-oxadiazolin-3-yl) -5- (n-propoxymethyleneamino) -4-trifluoromethylsulfonylpyrazole mp. 111 ~ 112 ℃

[0151]

Reference Example 2 5-amino-1- (2,6-dichloro-4)
-Trifluoromethylphenyl) -3- (N ¹ -ethyl-
N ² -Hydroxyamidino) -4-trifluoromethylsulfinylpyrazole 5-amino-1- (2,6-dichloro-4-trifluoromethylphenyl) -3- (5-methyl-1,2,4-
Oxadiazol-3-yl) -4-trifluoromethylsulfinylpyrazole (10.1 g, 20.5 mmol) in 100 ml
After dissolving in THF, 5.58 g (40.9 mmol) of zinc chloride and 1.76 g (41.9 mmol) of sodium borohydride were added. After stirring at room temperature for 5 days, the reaction mixture was poured into 150 ml of water. Ethyl acetate 1
00 ml was added, and the resulting precipitate was filtered using Celite. The filtrate was washed twice with 100 ml of a saturated saline solution, dried over anhydrous magnesium sulfate, and the solvent was distilled off to obtain a yellow-brown amorphous. This was subjected to silica gel column chromatography (ethyl acetate: hexane = 1: 2) to give 6.45.
g (13.0 mmol) of 5-amino-1- (2,6-dichloro-4-trifluoromethylphenyl) -3- (N ¹ -ethyl-N ² -hydroxyamidino) -4-trifluoromethylsulfinylpyrazole. Obtained as a pale yellow amorphous. 63% yield. NMR (CDCl ₃ , δ) 1.15 (3H, t, J = 7Hz), 3.47-3.62 (2H, m),
5.07 (1H, t, J = 6.3Hz), 5.14 (2H, br), 7.24 (1H, br),
7.80 (2H, s)

[0152]

[Reference Example 3] 1- (2,6-dichloro-4-trifluoromethylphenyl) -5-dimethylaminomethyleneamino-3- (delta ^{2-1,2,4-oxadiazoline-3-}
Yl) -4-trifluoromethylsulfinylpyrazole 5-amino-1- (2,6-dichloro-4-trifluoromethylphenyl) -3- (Δ ² -1,2,4-oxadiazolin-3-yl ) -4-trifluoromethylsulfinylpyrazole 0.91 g (1.89 mmol), toluene 10 ml, N, N-dimethylformamide dimethyl acetal 0.56 ml (purity 90%; 3.79 mmol) was further added, and the mixture was stirred at 80 ° C. for 4 hours. . The solvent was distilled off, and the obtained colorless oil was subjected to silica gel column chromatography (ethyl acetate: chloroform = 1: 10).
Recrystallized with a mixed solvent of hexane and 0.56 g (1.03 mmol) of 1
-(2,6-dichloro-4-trifluoromethylphenyl) -5-dimethylaminomethyleneamino-3- (Δ ²
-1,2,4-oxadiazolin-3-yl) -4-trifluoromethylsulfinylpyrazole was obtained as colorless crystals. Yield 55% mp. 171~173 ℃ NMR ( CDCl 3, δ) 2.79 (3H, s), 3.08
(3H, s), 5.24 (br, 1H), 5.
41 (1H, dd, J = 1 Hz, 3 Hz,);
47 (1H, dd, J = 1 Hz, 3 Hz), 7.7
0-7.74 (2H, m), 8.56 (1H, s)

[0153]

Reference Example 4 5-amino-1- (2,6-dichloro-4)
- trifluoromethylphenyl) -3- (4-diisopropoxy-methyl - [delta ^{2-1,2,4-oxadiazolin-3-yl)} -4-trifluoromethylsulfonyl pyrazole 5-amino-1- (2 , 6-dichloro-4-trifluoromethylphenyl) -3- (delta ^{2-1,2,4-oxadiazolin-3-yl)} -4-trifluoromethylsulfonyl pyrazole 1.00 g (2.01 mmol) orthoformate It was dissolved in 5 ml of triisopropyl. 20 mg of paratoluenesulfonic acid monohydrate was added to the reaction solution, and the mixture was stirred at 90 ° C for 34 hours.
The reaction solution was subjected to silica gel column chromatography (n-hexane: acetone = 5: 1) to obtain pale yellow crystals. The obtained crystals were recrystallized from petroleum ether-acetone to give 5-amino-1- (2,6-dichloro-4-trifluoromethylphenyl) -3- (4-diisopropoxymethyl-Δ ² as colorless crystals. 360 mg (0.57 mmol) of -1,2,4-oxadiazolin-3-yl) -4-trifluoromethylsulfonylpyrazole was obtained. Yield 29% mp. 173-176 ° C NMR (CDCl ₃ + DMSO-d ₆ , δ) 1.10 (6H, d, J = 6Hz), 1.11 (6H,
d, J = 6Hz), 3.85 (2H, sep, J = 6Hz), 5.54 (2H, s), 5.66
(1H, s), 6.58 (2H, br), 7.80 (2H, d, J = 0.5Hz)

[0154]

Reference Example 5 3- (4-acetyl-Δ ² -1,2,4-
Oxadiazolin-3-yl) -1- (2,6-dichloro-4-trifluoromethylphenyl) -5-methoxymethyleneamino-4-trifluoromethylsulfinylpyrazole 1- (2,6-dichloro-4- (Trifluoromethylphenyl) -5-methoxymethyleneamino-3- (Δ ² −
520 mg (1.00 mmo of 1,2,4-oxadiazolin-3-yl) -4-trifluoromethylsulfinylpyrazole
l) was suspended in 10 ml of acetonitrile. Pyridine 82 mg (1.04 mmol) was added to the reaction solution, and acetic anhydride 106 mg (1.04 mmol)
Of acetonitrile was added dropwise at room temperature, and
Stir for 18 hours. 4-Dimethylaminopyridine 1
27 mg (1.04 mmol) was added, and the mixture was further stirred at room temperature for 5 hours.
The reaction solution was concentrated under reduced pressure, and the concentrated residue was subjected to silica gel column chromatography (n-hexane: ethyl acetate =
5: 1), 530 mg of colorless crystals were obtained. The crystals were recrystallized from ethyl acetate-n-hexane to give 3- (4
-Acetyl-Δ ² -1,2,4-oxadiazoline-3
-Yl) -1- (2,6-dichloro-4-trifluoromethylphenyl) -5-methoxymethyleneamino-4-
400 mg of trifluoromethylsulfinylpyrazole (0.
70 mmol) were obtained. Yield 70% mp. 126-127 ° C NMR (CDCl ₃ , δ) 2.14 (3H, s), 3.70 (3H, s), 5.82 (1H,
d, J = 3Hz), 6.01 (1H, d, J = 3Hz), 7.78 (2H, m), 8.64 (1
H, s)

[0155]

Reference Example 6 1- (2,6-dichloro-4-trifluoromethylphenyl) -5-ethoxymethyleneamino-3
-(4-propionyl- [Delta] ² -l, 2,4-oxadiazolin-3-yl) -4-trifluoromethylsulfinylpyrazole 1- (2,6-dichloro-4-trifluoromethylphenyl) -5- Ethoxymethyleneamino-3- (Δ ² −
1,2,4-oxadiazolin-3-yl) -4-trifluoromethylsulfinylpyrazole 550 mg (1.02 mmol
l) was suspended in 10 ml of acetonitrile. Pyridine 0.09 ml (1.23 mmol), propionic anhydride 0.157 ml (1.2
3 mmol), 4-dimethylaminopyridine (DMAP) 150
mg (1.23 mmol) was added, and the mixture was stirred at room temperature for 4 hours. The reaction solution was concentrated under reduced pressure, and the concentrated residue was subjected to silica gel column chromatography (n-hexane: ethyl acetate = 2:
1), a colorless liquid was obtained. The liquid was crystallized from isopropyl ether-petroleum ether to give 1- (2,
6-dichloro-4-trifluoromethylphenyl) -5
-Ethoxymethyleneamino-3- (4-propionyl-
Δ ² -1,2,4-oxadiazolin-3-yl) -4
-440 mg of trifluoromethylsulfinylpyrazole
(0.74 mmol) was obtained. Yield 72% mp. 114-115 ° C NMR (CDCl ₃ , δ) 1.07 (3H, t, J = 7H
z), 1.22 (3H, t, J = 7 Hz),
37 (2H, m), 4.12 (2H, m), 5.8
1 (1H, d, J = 3 Hz), 6.02 (1H, d, J = 3 Hz)
7. d, J = 3 Hz), 7.76 (2H, m),
61 (1H, s)

[0156]

Reference Example 7 1- (2,6-dichloro-4-trifluoromethylphenyl) -5-ethoxymethyleneamino-3
-(4-methylcarbamoyl- [Delta] ² -l, 2,4-oxadiazolin-3-yl) -4-trifluoromethylsulfinylpyrazole 1- (2,6-dichloro-4-trifluoromethylphenyl) -5 -Ethoxymethyleneamino-3- (Δ ² −
1,2,4-oxadiazolin-3-yl) -4-trifluoromethylsulfinylpyrazole 550 mg (1.02 mmol
l) was suspended in 10 ml of acetonitrile. 0.124 ml (2.04 mmol) of methyl isocyanate was added to the reaction solution, and the mixture was stirred at room temperature for 45 hours. 0.285 ml of triethylamine (2.04 mmo
l), 0.124 ml (2.04 mmol) of methyl isocyanate was added,
Stirred at room temperature for another 24 hours. The reaction solution was concentrated under reduced pressure,
The concentrated residue was subjected to silica gel column chromatography (n-hexane: ethyl acetate = 2: 1) to obtain a pale yellow liquid. The liquid ethyl acetate - was crystallized with petroleum ether, as colorless crystals of 1- (2,6-dichloro-4-trifluoromethylphenyl) -5-ethoxymethyleneamino-3- (4-methylcarbamoyl - [delta ² -1 , 2,4
370 mg (0.62 mmol) of -oxadiazolin-3-yl) -4-trifluoromethylsulfinylpyrazole was obtained. Yield 61% mp. 115-116 ° C NMR (CDCl ₃ , δ) 1.21 (3H, t, J = 7Hz), 2.75 (3H, d, J = 5H
z), 4.11 (2H, m), 5.83 (1H, d, J = 2.Hz), 6.13 (1H, d, J =
2Hz,), 7.22 (1H, m), 7.80 (2H, m), 8.56 (1H, s)

[0157]

[Reference Example 8] 1- (2,6-dichloro-4-trifluoromethylphenyl) -3- (4-diethylcarbamoyl - [delta ^{2-1,2,4-oxadiazolin-3-yl)} -
5-ethoxymethyleneamino-4-trifluoromethylsulfinylpyrazole bistrichloromethyl carbonate (BTC) 56.2 mg (0.189 mmol) as T
It was dissolved in 5 ml of HF and cooled on ice. Pyridine 0.0496m in the reaction solution
l (0.613 mmol) was added and the mixture was stirred at room temperature for 1 hour. 1 in the reaction solution
- (2,6-dichloro-4-trifluoromethylphenyl) -5-ethoxymethyleneamino -3- (Δ ² -1,
300 mg (0.557 mmol) of 2,4-oxadiazolin-3-yl) -4-trifluoromethylsulfinylpyrazole
A solution of 5 ml of THF was added dropwise over 5 minutes under ice cooling, and the mixture was stirred at room temperature for 1 hour. After the reaction, 0.115 ml of diethylamine (1.11 m
mol) and stirred at room temperature for 6 hours. The precipitated crystals were removed by filtration, the filtrate was concentrated under reduced pressure, and the concentrated residue was subjected to silica gel column chromatography (n-hexane: ethyl acetate = 3: 1) to give 1- (2,6-dichloro- as colorless crystals. 4-trifluoromethylphenyl) -3- (Δ ² -4
-Diethylcarbamoyl-1,2,4-oxadiazolin-3-yl) -5-ethoxymethyleneamino-4-trifluoromethylsulfinylpyrazole in 220 mg (0.3
4 mmol). Yield 62% mp. 107-108 ° C NMR (CDCl ₃ , δ) 1.14 (6H, t, J = 7Hz), 1.19 (3H, t, J = 7H
z), 3.30 (4H, q, J = 7Hz), 4.08 (2H, m), 5.48 (1H, d, J = 1H
z), 5.55 (1H, d, J = 1Hz), 7.72 (2H, m), 8.58 (1H, s)

[0158]

[Reference Example 9] 1- (2,6-dichloro-4-trifluoromethylphenyl) -3- (4-dimethylamino-acetyl - [delta ^{2-1,2,4-oxadiazolin-3-yl)}
-5-ethoxymethyleneamino-4-trifluoromethylsulfinylpyrazole 1- (2,6-dichloro-4-trifluoromethylphenyl) -5-ethoxymethyleneamino-3- (Δ ² −
1,2,4-oxadiazolin-3-yl) -4-trifluoromethylsulfinylpyrazole 500 mg (0.93 mmol
l) was suspended in 10 ml of acetonitrile. Hydrochloric acid N, N
-Dimethylglycine 127mg (0.93mmol), BOP reagent 410mg
(0.93 mmol) and 0.26 ml (1.86 mmol) of triethylamine were added, and the mixture was stirred at room temperature for 55 hours. The reaction solution was concentrated under reduced pressure, and the concentrated residue was subjected to silica gel column chromatography (n-hexane: ethyl acetate = 2: 1) to remove colorless crystals by 270.
mg was obtained. The crystals propyl ether - was recrystallized from hexane, as colorless crystals of 1- (2,6-dichloro-4-trifluoromethylphenyl) -3- (4-dimethylamino-acetyl - [delta ^2-1,2,4- Oxadiazoline-3
-Yl) -5-ethoxymethyleneamino-4-trifluoromethylsulfinylpyrazole in 150 mg (0.24 mmo
l) Got it. Yield 26% mp. 135 ° C NMR (CDCl ₃ , δ) 1.22 (3H, t, J = 7Hz), 2.11 (6H, s), 2.95
(1H, d, J = 14Hz), 3.40 (1H, d, J = 14Hz), 4.11 (m, 2H), 5.
60 (1H, d, J = 4Hz), 6.11 (1H, d, J = 4Hz), 7.76 (2H, m), 8.
72 (1H, s)

[0159]

Reference Example 10 5-amino-1- (2,6-dichloro-
4-trifluoromethylphenyl) -3- (4-ethyl-Δ ² -1,2,4-oxadiazolin-3-yl)-
4-trifluoromethylsulfinylpyrazole 1.0 g of 5-amino-1- (2,6-dichloro-4-trifluoromethylphenyl) -3- (N1-ethyl-N2-hydroxyamidino) -4-trifluoromethylsulfinylpyrazole (2.0 mmol) was dissolved in 15 ml of acetonitrile, and 0.8 ml (11 mmol) of a 37% aqueous solution of formalin was added.
Drops were added, and the mixture was heated under reflux for 7 hours. After the reaction, 60 ml of ethyl acetate was added, and the mixture was added three times with 40 ml of a saturated aqueous solution of sodium bicarbonate and 20 ml of a saturated saline solution.
And washed twice. After drying over anhydrous magnesium sulfate, the solvent was distilled off to obtain a pale yellow amorphous. This was subjected to silica gel column chromatography (n-hexane: ethyl acetate = 3: 1), and 500 mg (0.98 mmol) of 5-
Amino-1- (2,6-dichloro-4-trifluoromethylphenyl) -3- (4-ethyl - [delta ² -1,2,4
-Oxaziazolin-3-yl) -4-trifluoromethylsulfinylpyrazole was obtained as a colorless amorphous. Yield 49%. NMR (CDCl ₃ , δ) 1.14 (3H, t, J = 7Hz), 3.4-3.7 (2H, m),
5.18 (2H, br), 5.38 (2H, d, J = 7Hz), 7.82 (2H, s)

[0160]

[Reference Example 11] 3- (4-acetyl - △ ² -1,2,4
-Oxadiazolin-3-yl) -1- (2,6-dichloro-4-trifluoromethylphenyl) -5-ethoxymethyleneamino-4-trifluoromethylsulfinylpyrazole 1- (2,6-dichloro-4 -Trifluoromethylphenyl) -5-ethoxymethyleneamino-3- (Δ ² −
0.89 g (1.7 mm) of 1,2,4-oxadiazolin-3-yl) -4-trifluoromethylsulfinylpyrazole
ol) in 10 ml of acetonitrile, 0.21 g (1.72 mmol) of 4-dimethylaminopyridine, 0.16 ml of acetic anhydride (1.7 m
mol) and stirred at room temperature for 2.5 hours. After the reaction, the solvent was distilled off, and 70 ml of ethyl acetate was added. 2 with 20 ml of saturated aqueous sodium bicarbonate
It was washed twice with 30 ml of saturated saline. After drying over anhydrous magnesium sulfate and evaporating the solvent, a pale yellow amorphous was obtained. This was subjected to silica gel column chromatography (n-hexane: ethyl acetate = 2: 1), and the obtained colorless crystals were recrystallized from chloroform-n-hexane.
160mg of (0.27mmol) 3- (4- acetyl - [delta ² -1,
2,4-oxadiazolin-3-yl) -1- (2,6
-Dichloro-4-trifluoromethylphenyl) -5-
Ethoxymethyleneamino-4-trifluoromethylsulfinylpyrazole was obtained as colorless crystals. Yield 16%. mp. 116-118 ° C NMR (CDCl ₃ , δ) 1.22 (3H, t, J = 7Hz), 2.14 (3H, s), 4.2
0-4.25 (2H, m), 5.83 (1H, d, J = 3Hz), 6.01 (1H, d, J = 3Hz),
7.76-7.80 (2H, m), 8.60 (1H, s)

[0161]

Reference Example 12 5-amino-1- (2,6-dichloro-
4-trifluoromethylphenyl) -3- {4- (N,
N-Diethylcarbamoyl) -Δ ² -1,2,4-oxadiazolin-3-yl} -4-trifluoromethylthiopyrazole 318 mg (1.07 mmol) of bistrichloromethyl carbonate (BTC) in THF
It was dissolved in 6 ml and cooled on ice. 255 mg of pyridine (3.22
mmol) and stirred at room temperature for 30 minutes. To the reaction solution of 5-amino-1- (2,6-dichloro-4-trifluoromethylphenyl) -3- (delta ^{2-1,2,4-oxadiazolin-3-yl)} -4-trifluoromethylthio Pyrazole
A solution of 1.00 g (2.15 mmol) in 6 ml of THF was added dropwise under ice cooling, and the mixture was stirred at the same temperature for 30 minutes. After the reaction, 472 mg of diethylamine (6.
45 mmol), and the mixture was stirred under ice cooling for 3 hours and then at room temperature for 3 hours. The mixture was poured into 100 ml of ice water and extracted with 100 ml of ethyl acetate. After drying over anhydrous magnesium sulfate and concentration, the obtained residue was subjected to silica gel column chromatography (n-hexane: ethyl acetate = 1: 1) to give 370 mg (0.65 mmol).
The title compound was obtained as colorless crystals of l). Yield 30% mp. 81-83 ° C NMR (CDCl ₃ , δ) 1.16 (6H, t, J = 7Hz), 3.30 (4H, q, J = 7H
z), 4.34 (2H, s), 5.51 (2H, s), 7.76 (2H, s)

[0162]

[Reference Example 13] 1- (2,6-dichloro-4-trifluoromethylphenyl) -3- {4- (N, N- diethylcarbamoyl) - [delta ^{2-1,2,4-oxadiazoline} -3 -Yl} -5-ethoxymethyleneamino-4-trifluoromethylthiopyrazole 5-amino-1- (2,6-dichloro-4-trifluoromethylphenyl) -3- {4- (N, N-diethylcarbamoyl) - [delta ^{2-1,2,4-oxadiazoline} -
3-yl} -4-trifluoromethylthiopyrazole 37
0 mg (0.65 mmol) was dissolved in 3 ml of triethyl orthoformate.
Add 50 mg of paratoluenesulfonic acid monohydrate to the reaction solution,
Stirred at room temperature for 3 hours. The reaction solution was concentrated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography (n
-Hexane: ethyl acetate = 2: 1), 290 mg (0.47 mmol) of the title compound as colorless crystals. Yield 72% mp. _{93-95 ℃ NMR (CDCl 3, δ} ) 1.26-1.14 (9H, m), 3.30 (4H, q, J = 7H
z), 4.13 (2H, q, J = 7Hz), 5.55 (2H, s), 7.70 (2H, s), 8.
33 (1H, s)

[0163]

Reference Example 14 5-amino-1- (2,6-dichloro-
4-trifluoromethylphenyl) -3- {4- (N,
N- dimethylcarbamoyl) - [delta ^{2-1,2,4-oxadiazolin-3-yl}} -4-trifluoromethyl methylsulfinyl pyrazole carbonate bistrichloromethyl (BTC) 615mg (2.07mmol) was dissolved in THF
It was dissolved in 12 ml and cooled on ice. Pyridine 492 mg (6.2
2 mmol) and stirred at room temperature for 30 minutes. To the reaction solution of 5-amino-1- (2,6-dichloro-4-trifluoromethylphenyl) -3- (delta ^{2-1,2,4-oxadiazolin-3-yl)} -4-trifluoromethyl A solution of 2.00 g (4.15 mmol) of sulfinylpyrazole in 12 ml of THF was added dropwise under ice cooling, and the mixture was stirred at the same temperature for 30 minutes. After the reaction, 1.12 g (12.4 mmol) of a 50% aqueous dimethylamine solution was added, and the mixture was stirred for 1 hour under ice cooling. The mixture was poured into 100 ml of ice water and extracted with 100 ml of ethyl acetate. Drying over anhydrous magnesium sulfate and concentration gave 2.26 g (4.08 mmol) of the title compound as colorless crystals. Yield 98% mp. 207.0-207.5 ° C NMR (CDCl ₃ , δ) 2.93 (6H, s), 5.14 (2H, s), 5.46 (1H,
d, J = 2Hz), 5.52 (1H, d, J = 2Hz), 7.78 (2H, s)

[0164]

Reference Example 15 5-amino-1- (2,6-dichloro-
4-trifluoromethylphenyl) -3- {4- (N,
N- diethylcarbamoyl) - [delta ^{2-1,2,4-oxadiazolin-3-yl}} -4-trifluoromethyl methylsulfinyl pyrazole carbonate bistrichloromethyl (BTC) 113mg (0.38mmol) was dissolved in THF
It was dissolved in 10 ml and cooled on ice. 0.0923 ml of pyridine in the reaction solution
(1.14 mmol), and the mixture was stirred at room temperature for 30 minutes. To the reaction solution of 5-amino-1- (2,6-dichloro-4-trifluoromethylphenyl) -3- (delta ^{2-1,2,4-oxadiazolin-3-yl)} -4-trifluoromethyl A solution of 500 mg (1.04 mmol) of sulfinylpyrazole in 5 ml of THF was added dropwise under ice cooling, and the mixture was stirred at room temperature for 1 hour. After the reaction, 0.322 ml (3.11 mmol) of diethylamine was added, and the mixture was stirred at room temperature for 15.5 hours. The precipitated crystals were removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (n-
Hexane: ethyl acetate = 2: 1) to obtain colorless crystals. This was recrystallized from a mixed solvent of n-hexane and ethyl acetate to give 26
0 mg (0.45 mmol) of the title compound was obtained as colorless crystals. Yield 43% mp. 98.0-99.0 ° C NMR (CDCl ₃ , δ) 1.13 (6H, t, J = 7Hz), 3.30 (4H, q, J = 7H
z), 5.13 (2H, s), 5.43 (1H, d, J = 1Hz), 5.50 (1H, d, J = 1)
Hz), 7.78 (2H, s)

[0165]

[Reference Example 16] 1- (2,6-dichloro-4-trifluoromethylphenyl) -3- {4- (N, N- diethylcarbamoyl) - [delta ^{2-1,2,4-oxadiazoline} -3 -Yl｝ -5-ethoxymethyleneamino-4-trifluoromethylsulfonylpyrazole 119 mg (0.401 mmol) of bistrichloromethyl carbonate (BTC) in TH
F was dissolved in 10 ml and cooled on ice. 0.0974 ml of pyridine in the reaction solution
(1.20 mmol) and 1- (2,6-dichloro-4-).
Trifluoromethylphenyl) -5-ethoxymethyleneamino -3- (Δ ² -1,2,4- oxadiazoline -
A solution of 400 mg (0.803 mmol) of 3-yl) -4-trifluoromethylsulfonylpyrazole in 5 ml of THF was added dropwise under ice cooling, and the mixture was stirred at the same temperature for 2 hours. After the reaction, diethylamine
Dissolve 0.332 ml (3.21 mmol) in 5 ml of THF and add
Stirred at room temperature for 30 minutes. The reaction solution was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (n-hexane: ethyl acetate = 1: 1) to obtain 130 mg (0.20 mmol) of the title compound as colorless crystals. Yield 25% mp. 105.5-106.5 ° C NMR (CDCl ₃ , δ) 1.17 (6H, t, J = 7Hz), 1.23 (3H, t, J = 6H
z), 3.27 (4H, q, J = 7Hz), 4.16 (2H, q, J = 6Hz), 5.64 (2H,
s), 7.74 (2H, s), 8.04 (1H, s)

[0166]

[Reference Example 17] 1- (2,6-dichloro-4-trifluoromethylphenyl) -3- {4- (N, N- dimethylcarbamoyl) - [delta ^{2-1,2,4-oxadiazoline} -3 -Yl｝ -5-ethoxymethyleneamino-4-trifluoromethylsulfinylpyrazole bistrichloromethyl carbonate (BTC) 91.2 mg (0.310 mmol) as T
It was dissolved in 5 ml of HF and cooled on ice. 0.0751 ml of pyridine in the reaction solution
(0.929 mmol), and the mixture was stirred at room temperature for 1 hour. Further 1-
(2,6-dichloro-4-trifluoromethylphenyl) -5-ethoxymethyleneamino -3- (Δ ² -1,
2,4-oxadiazolin-3-yl) -4-trifluoromethylsulfinylpyrazole 500 mg (0.929 mmol)
A solution of 5 ml of THF was added dropwise under ice cooling, and the mixture was stirred at room temperature for 1 hour. After the reaction, 0.167 ml of 50% aqueous dimethylamine solution (1.86 mm
ol) was dissolved in 5 ml of THF and added dropwise, followed by stirring at room temperature for 3.5 hours. The reaction solution was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (n-hexane: ethyl acetate = 2: 1) to obtain 210 mg (0.34 mmol) of the title compound as a colorless amorphous. Yield 37% NMR (CDCl ₃ , δ) 1.20 (3H, t, J = 7Hz), 2.94 (6H, s), 4.1
0 (2H, m), 5.51 (1H, d, J = 2Hz), 5.58 (1H, d, J = 2Hz), 7.
72 (2H, m), 8.56 (1H, s)

[0167]

Reference Example 18 1- (2,6-dichloro-4-trifluoromethylphenyl) -3- {4- (N-ethyl-N-
Methylcarbamoyl) -Δ ² -1,2,4-oxadiazolin-3-yl} -5-ethoxymethyleneamino-4
-Trifluoromethylsulfinylpyrazole bistrichloromethyl carbonate (BTC) 138 mg (0.47 mmol) in THF
It was dissolved in 3 ml and cooled on ice. Pyridine 111 mg (1.40
mmol), and the mixture was stirred under ice cooling for 30 minutes. Furthermore, 1- (2,
6-dichloro-4-trifluoromethylphenyl) -5
- ethoxymethyleneamino -3- (Δ ² -1,2,4-
A solution of 500 mg (0.93 mmol) of oxadiazolin-3-yl) -4-trifluoromethylsulfinylpyrazole in 3 ml of THF was added dropwise under ice-cooling, and the mixture was stirred at the same temperature for 30 minutes. After the reaction,
110 mg (1.86 mmol) of ethyl methylamine was added to 1 ml of THF
, And added dropwise, followed by stirring at room temperature for 21 hours. The mixture was poured into 100 ml of ice water and extracted with 100 ml of ethyl acetate. After drying over anhydrous magnesium sulfate and concentration, the residue was subjected to silica gel column chromatography (n-hexane: ethyl acetate =
3: 1), 100 mg (0.16 mmol) of the title compound was obtained as a colorless amorphous. Yield 17% mp. 113-114 ° C NMR (CDCl ₃ , δ) 1.14 (3H, t, J = 7Hz), 1.20 (3H, t, J = 7H
z), 2.93 (3H, s), 3.31 (2H, q, J = 7Hz), 4.30-3.90 (2H,
m), 5.50 (1H, s), 5.57 (1H, s), 7.72 (2H, s), 8.58 (1H,
s)

[0168]

REFERENCE EXAMPLE 19 1- (2,6-Dichloro-4-trifluoromethylphenyl) -3- {4- (N, N-diethylcarbamoyl) -Δ ² -1,2,4-oxadiazoline-3 -Yl} -5-isopropoxymethyleneamino-4
-Trifluoromethylsulfinylpyrazole bistrichloromethyl carbonate (BTC) 85.3 mg (0.287 mmol)
It was dissolved in 10 ml of HF and cooled on ice. Pyridine 0.0769m in the reaction solution
l (0.951 mmol) was added dropwise, and 1- (2,6-dichloro-4-trifluoromethylphenyl) -5-isopropoxymethyleneamino-3- (Δ ² -1,2,4-oxadiazoline- A solution of 500 mg (0.905 mmol) of 3-yl) -4-trifluoromethylsulfinylpyrazole in 5 ml of THF was added dropwise under ice cooling, and the mixture was stirred at room temperature for 1 hour. The reaction solution was cooled on ice, and 0.192 ml (1.86 mmol) of diethylamine was added to 5 ml of T
Dissolved in HF and added dropwise, and stirred at room temperature for 22.5 hours. The reaction solution was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (n-hexane: ethyl acetate = 2:
1), 240 mg (0.37 mmol) of the title compound was obtained as a colorless liquid. Yield 41% NMR (CDCl ₃ , δ) 0.82 (3H, t, J = 7Hz), 1.14 (6H, t, J = 7H
z), 1.58 (2H, m), 3.30 (4H, q, J = 7Hz), 3.99 (2H, m), 5.
48 (1H, d, J = 1Hz), 5.55 (1H, d, J = 1Hz), 7.72 (2H, m),
8.61 (1H, s)

[0169]

Reference Example 20 1- (2,6-dichloro-4-trifluoromethylphenyl) -5-ethoxymethyleneamino-
3- {4- pivaloyl - [delta ^{2-1,2,4-oxadiazolin-3-yl}} -4-trifluoromethyl methylsulfinyl pyrazole 1- (2,6-dichloro-4-trifluoromethylphenyl) -5 -Ethoxymethyleneamino-3- (Δ ² −
1,2,4-oxadiazolin-3-yl) -4-trifluoromethylsulfinylpyrazole 500 mg (0.929 mmo
l) was suspended in 10 ml of acetonitrile. 0.142 ml (1.02 mmol) of triethylamine and 0.166 ml of pivaloyl chloride were added to the reaction solution.
(1.02 mmol), 5 mg of 4-dimethylaminopyridine,
Stirred at room temperature for 4 days. The reaction solution was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (n-hexane: ethyl acetate = 3: 1) to give 220 mg (0.35 mmol) of the title compound as colorless crystals. Yield 38% mp. 133.5-134.0 ° C NMR (CDCl ₃ , δ) 1.21 (3H, t, J = 7Hz), 1.28 (9H, s), 4.1
1 (2H, m), 5.71 (1H, d, J = 2Hz), 5.88 (1H, d, J = 2Hz), 7.
72 (1H, s), 7.73 (1H, s), 8.54 (1H, s)

[0170]

Reference Example 21 3- {4- (t-butoxycarbonyl)
-Δ ² -1,2,4-oxadiazolin-3-yl}-
1- (2,6-dichloro-4-trifluoromethylphenyl) -5-ethoxymethyleneamino-4-trifluoromethylsulfinylpyrazole 1- (2,6-dichloro-4-trifluoromethylphenyl) -5-ethoxy Methyleneamino-3- (Δ ² −
538 mg (1.00 mmo of 1,2,4-oxadiazolin-3-yl) -4-trifluoromethylsulfinylpyrazole
l) was dissolved in 10 ml of acetonitrile, and 0.097 ml (1.20 mmol) of pyridine and Di-t-butyldicarbona were stirred at room temperature.
270 mg (1.2 mmol) of te were added. Further, 147 mg (1.20 mmol) of 4-dimethylaminopyridine was added, and the mixture was stirred at room temperature for 2 hours.
The reaction solution was concentrated under reduced pressure, and then subjected to silica gel column chromatography (n-hexane: ethyl acetate = 4: 1).
mg (0.76 mmol) of the title compound were obtained as a colorless amorphous. Yield 76% NMR (CDCl ₃ , δ) 1.22 (3H, t, J = 7Hz), 1.45 (9H, s), 3.9
8-4.26 (2H, m), 5.73 (1H, d, J = 2Hz), 5.78 (1H, d, J = 2H
z), 7.72-7.78 (2H, m), 8.61 (1H, s)

[0171]

Reference Example 22 1- (2,6-Dichloro-4-trifluoromethylphenyl) -3- {4- (N, N-diethylcarbamoyl) -Δ ² -1,2,4-oxadiazoline-3 -Yl} -5-dimethylaminomethyleneamino-4
-Trifluoromethylsulfinylpyrazole bistrichloromethyl carbonate (BTC) 0.14 g (0.47 mmol) in THF
After dissolving in 5 ml and cooling with ice, 0.13 ml (1.62 mmol) of pyridine was added. The mixture was stirred at room temperature for 35 minutes, and 1- (2,6-dichloro-4-trifluoromethylphenyl) -5-dimethylaminomethyleneamino-3- dissolved in 5 ml of THF was added thereto.
(Delta ^{2-1,2,4-oxadiazolin-3-yl)} -
0.45 g of 4-trifluoromethylsulfinylpyrazole
(0.84 mmol) was added dropwise under ice cooling. After the dropwise addition, the mixture was stirred at room temperature for 1 hour, and 0.18 ml (1.74 mmol) of diethylamine was injected under ice cooling. Thereafter, the mixture was stirred for 30 minutes under ice-cooling and for 12 hours at room temperature. Then, 0.09 ml (0.86 mmol) of diethylamine was added, and the mixture was further stirred at room temperature for 1.5 hours. 20 ml of water and 20 ml of saturated saline were added, and the mixture was extracted with 40 ml of ethyl acetate. The ethyl acetate layer was washed with saturated saline (20 ml × 2) and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the obtained reaction mixture was subjected to silica gel column chromatography (ethyl acetate: hexane = 1: 1).
And purified. The crystals obtained after the silica gel column were washed with ethyl acetate: hexane = 1: 5 and recrystallized from a mixed solvent of ethyl acetate-hexane (20 ml) to obtain 0.30 g (0.47 mmol) of the title compound as colorless crystals. Yield 57% mp. 156-158 ° C NMR (CDCl ₃ , δ) 1.14 (6H, t, J = 7.2Hz), 2.78 (3H, s),
3.07 (3H, s), 3.30 (4H, q, J = 7Hz), 5.47 (1H, d, J = 1Hz),
5.54 (1H, d, J = 1Hz,), 7.66-7.71 (2H, m), 8.65 (s, 1H)

The ¹ H-NMR spectra of the oils and amorphous substances in Tables 37 to 70 are shown below. 1) NMR (CDCl ₃ , δ) 1.09 (6H, d, J = 7Hz), 1.25 (3H, t, J = 7H
z), 2.61 (1H, qu, J = 7Hz), 4.16 (2H, q, J = 7Hz), 5.93 (2
H, s), 7.76 (2H, s), 8.37 (1H, s) 2) NMR (CDCl ₃ , δ) 1.10 (6H, d, J = 8Hz), 1.22 (3H, t, J = 7H
z), 2.80 (1H, m), 4.12 (2H, m), 5.81 (1H, d, J = 3Hz), 6.
00 (1H, d, J = 3Hz), 7.76 (2H, m), 8.60 (1H, s) 3) NMR (CDCl ₃ , δ) 0.83 (3H, t, J = 8Hz), 1.08 (3H, d, J = 7H
z), 1.25 (3H, t, J = 7Hz), 1.30-1.80 (1H, m), 2.44 (2H,
q, J = 7Hz), 4.16 (2H, q, J = 7Hz), 5.87 (1H, d, J = 2Hz), 6.
00 (1H, d, J = 2Hz), 7.75 (2H, s), 8.37 (1H, s) 4) NMR (CDCl 3, δ) 1.23 (3H, t, J = 7Hz), 1.31 (9H, s) , 2.
44 (2H, q, J = 7Hz), 4.14 (2H, q, J = 7Hz), 5.84 (2H, s), 7.
71 (2H, s), 8.34 (1H, s) 5) NMR (CDCl ₃ , δ) 1.20 (3H, t, J = 7Hz), 2.94 (6H, s), 4.
10 (2H, m), 5.51 (1H, d, J = 2Hz), 5.58 (1H, d, J = 2Hz),
7.72 (2H, m), 8.56 (1H, s) 6) NMR (CDCl ₃ , δ) 1.10 (3H, d, J = 6Hz), 1.23 (3H, d, J = 6H
z), 2.95 (6H, s), 4.84 (1H, qu, J = 6Hz), 5.51 (1H, d, J = 2H
z), 5.59 (1H, d , J = 2Hz), 7.73 (2H, s), 8.56 (1H, s) 7) NMR (CDCl 3, δ) 1.19 (6H, d, J = 6Hz), 2.92 (6H , s), 4.
94 (1H, qu, J = 6Hz), 5.67 (2H, s), 7.75 (2H, s), 8.00 (1
H, s) 8) NMR (CDCl ₃ , δ) 0.84 (3H, t, J = 7Hz), 1.20-1.40 (2H,
m), 1.5-1.6 (2H, m), 2.95 (6H, s), 4.10 (2H, dt, J = 1H
z, 6.6Hz), 5.58 (2H, s), 7.71-7.72 (2H, m), 8.35 (1H,
s) 9) NMR (CDCl ₃ , δ) 0.82 (3H, t, J = 7Hz), 1.14 (6H, t, J = 7H
z), 1.58 (2H, m), 3.30 (4H, q, J = 7Hz), 3.99 (2H, m),
5.48 (1H, d, J = 1Hz), 5.55 (1H, d, J = 1Hz), 7.72 (2H, m),
8.61 (1H, s) 10) NMR (CDCl ₃ , δ) 0.84 (3H, t, J = 7Hz), 1.16 (6H, t, J = 7
Hz), 1.61 (2H, m), 3.27 (4H, q, J = 7Hz), 4.07 (2H, t, J = 7
Hz), 5.63 (2H, s), 7.74 (2H, s), 8.06 (1H, s) 11) NMR (CDCl ₃ , δ) 1.17 (6H, t, J = 7Hz), 1.90 (6H, d, J = 6
Hz), 3.32 (4H, q, J = 7Hz), 4.93 (1H, qu, J = 6Hz), 5.55
(2H, s), 7.70 (2H, s), 8.29 (1H, s) 12) NMR (CDCl ₃ , δ) 1.12-1.23 (12H, m), 3.28 (4H, q, J = 7
Hz), 4.83-5.05 (1H, m), 5.63 (2H, s), 7.74 (2H, m), 7.99
(1H, s) 13) NMR (CDCl ₃ , δ) 0.84 (3H, t, J = 7Hz), 1.17 (6H, t, J = 7
Hz), 1.25-1.40 (2H, m), 1.49-1.63 (2H, m), 3.32 (4H,
q, J = 7Hz), 4.10 (2H, t, J = 6Hz), 5.55 (2H, s), 7.71 (2
H, s), 8.36 (1H, s) 14) NMR (CDCl ₃ , δ) 0.84 (3H, t, J = 7Hz), 1.17 (6H, t, J = 7
Hz), 1.22-1.36 (2H, m), 1.48-1.59 (2H, m), 3.28 (4H, m
q, J = 7Hz), 4.13 (2H, t, J = 6Hz), 5.64 (2H, s), 7.74 (2
H, s), 8.05 (1H, s) 15) NMR (CDCl ₃ , δ) 1.17 (3H, t, J = 7Hz), 1.26 (3H, t, J = 7
Hz), 2.90 (3H, s), 3.30 (2H, q, J = 7Hz), 4.17 (2H, d, J = 7H
z), 5.65 (2H, s ), 7.75 (2H, s), 8.05 (1H, s) 16) NMR (CDCl 3, δ) 1.26-1.14 (9H, m), 2.93 (3H, s), 3.
33 (2H, q, J = 7Hz), 4.94 (1H, qu, J = 6Hz), 5.57 (2H, s),
7.71 (2H, s), 8.29 (1H, s) 17) NMR (CDCl ₃ , δ) 1.17 (3H, t, J = 7Hz), 1.19 (6H, d, J = 6
Hz), 2.90 (3H, s), 3.29 (2H, q, J = 7Hz), 4.94 (1H, qu, J =
6Hz), 5.66 (2H, s), 7.75 (2H, s), 8.00 (1H, s) 18) NMR (CDCl ₃ , δ) 0.84 (3H, t, J = 7Hz), 1.33-1.14 (5H,
m), 1.57 (2H, qu, J = 6Hz), 2.93 (3H, s), 3.33 (4H, q, J =
7Hz), 4.10 (2H, t, J = 7Hz), 5.57 (2H, s), 7.71 (2H, s),
8.35 (1H, s) 19) NMR (CDCl ₃ , δ) 0.83 (3H, t, J = 7Hz), 1.17 (3H, t, J = 7
Hz), 1.25 (2H, m), 1.55 (2H, m), 2.89 (3H, s), 3.29 (2
(H, t, J = 7Hz), 4.13 (2H, t, J = 7Hz), 5.65 (2H, s), 7.74 (2
H, m), 8.05 (1H, s) 20) NMR (CDCl ₃ , δ) 1.14 (3H, t, J = 7Hz), 3.4-3.7 (2H,
m), 5.18 (2H, br ), 5.38 (2H, d, J = 7Hz), 7.82 (2H, s) 21) NMR (CDCl 3, δ) 1.14 (6H, d, J = 7Hz), 1.23 (3H , t, J = 7
Hz), 2.86 (3H, s), 4.17 (2H, q, J = 7Hz), 4.42 (1H, qu, J =
7Hz), 5.88 (2H, s ), 7.74 (2H, s), 8.03 (1H, s) 22) NMR (CDCl 3, δ) 1.23 (3H, t, J = 7Hz), 1.36 (9H, s),
2.93 (3H, s), 4.07-4.19 (2H, m), 5.56 (2H, s), 7.71 (2
H, s), 8.35 (1H, s) 23) NMR (CDCl ₃ , δ) 1.20 (3H, t, J = 7Hz), 1.35 (9H, s),
2.91 (3H, s), 4.00-4.19 (2H, m), 5.46 (1H, d, J = 2Hz),
5.57 (1H, d, J = 2Hz), 7.71-7.74 (2H, m), 8.60 (1H, s) 24) NMR (CDCl 3, δ) 1.23 (3H, t, J = 7Hz), 1.33 (9H, s),
4.17 (2H, q, J = 7Hz), 5.63 (2H, s), 7.75 (2H, s), 8.06 (1
H, s) 25) NMR (CDCl ₃ , δ) 1.12-1.26 (12H, m), 3.22 (2H, q, J = 7
Hz), 4.00-4.20 (2H, m), 5.48 (1H, d, J = 1Hz), 5.54 (1H,
d, J = 1Hz), 7.72-7.74 (2H, m), 8.59 (1H, s) 26) NMR (CDCl 3, δ) 1.20 (3H, t, J = 7Hz), 2.91 (3H, s),
4.03-3.73 (4H, m), 5.16 (1H, q, J = 2Hz), 5.23 (1H, d, J = 2
Hz), 5.48 (2H, d, J = 2Hz), 5.58 (1H, d, J = 2Hz), 5.66-5.
86 (1H, m), 7.74 (2H, s), 8.57 (1H, s) 27) NMR (CDCl ₃ , δ) 1.04 (3H, t, J = 7Hz), 1.14 (3H, t, J = 7
Hz), 1.20 (3H, t, J = 7Hz), 2.85 (2H, m), 3.52 (2H, m),
4.10 (2H, m), 5.66 (1H, d, J = 2Hz), 5.70 (1H, d, J = 2Hz),
7.71 (2H, m), 8.59 (1H, s) 28) NMR (CDCl ₃ , δ) 1.21 (3H, t, J = 7Hz), 3.99-4.26 (2H,
m), 5.75 (1H, d, J = 2Hz), 5.99 (1H, d, J = 2Hz), 7.69 (1H,
brs), 7.79 (2H, m ), 8.51 (1H, s), 9.77 (1H, s) 29) NMR (CDCl 3, δ) 1.21 (3H, t, J = 7Hz), 3.68 (3H, s), 3.99-
4.26 (2H, m), 5.80 (1H, d, J = 2Hz), 6.06 (1H, d, J = 2Hz),
7.81 (2H, m), 8.54 (1H, s), 9.90 (1H, s) 30) NMR (CDCl ₃ , δ) 1.21 (3H, t, J = 7Hz), 3.12 (3H, s),
3.98-4.25 (2H, m), 5.57 (1H, d, J = 3Hz), 5.71 (1H, d, J = 3
Hz), 7.70-7.82 (2H, m), 8.06 (1H, brs), 8.45 (1H, s) 31) NMR (CDCl ₃ , δ) 1.20 (3H, t, J = 7Hz), 1.00-1.50 (4H ,
m), 1.60-1.80 (6H, m), 2.83 (3H, s), 3.70-3.90 (1H, m),
4.00-4.20 (2H, m), 5.48 (1H, d, J = 2Hz), 5.55 (1H, d, J =
2Hz), 7.71-7.74 (2H, m), 8.58 (1H, s) 32) NMR (CDCl ₃ , δ) 1.20 (3H, t, J = 7Hz), 1.60 (6H, br),
3.30-3.40 (4H, m), 4.00-4.20 (2H, m), 5.49 (1H, d, J = 2
Hz), 5.56 (1H, d, J = 2Hz), 7.72-7.75 (2H, m), 8.59 (1
H, s) 33) NMR (CDCl ₃ , δ) 1.20 (3H, t, J = 7Hz), 2.25 (3H, s),
2.38 (4H, t, J = 5Hz), 3.46 (4H, t, J = 5Hz), 4.10 (2H, m),
5.59 (1H, d, J = 2Hz), 5.76 (1H, d, J = 2Hz), 7.73 (2H, m),
8.57 (1H, s) 34) NMR (CDCl ₃ , δ) 1.21 (3H, t, J = 7Hz), 3.42-3.47 (4H,
m), 3.67 (4H, t, J = 5Hz), 4.00-4.20 (2H, m), 5.49 (1H,
d, J = 2Hz), 5.57 (1H, d, J = 2Hz), 7.72-7.77 (2H, m), 8.5
7 (1H, s) 35) NMR (CDCl ₃ , δ) 0.81-1.67 (18H, m), 2.20-2.50 (2H,
m), 3.98-4.27 (2H, m), 5.82 (1H, d, J = 3Hz), 6.00 (1H,
d, J = 3Hz), 7.73-7.81 (2H, m), 8.61 (1H, s) 36) NMR (CDCl ₃ , δ) 0.81-1.67 (20H, m), 2.20-2.50 (2H, m
m), 3.98-4.27 (2H, m), 5.82 (1H, d, J = 3Hz), 6.00 (1H,
d, J = 3Hz), 7.73-7.81 (2H, m), 8.61 (1H, s) 37) NMR (CDCl ₃ , δ) 1.22 (3H, t, J = 7Hz), 1.45-1.74 (4H,
m), 2.55 (1H, m), 4.11 (2H, m), 5.81 (1H, d, J = 3Hz), 6.
04 (1H, d, J = 3Hz), 7.76 (2H, m), 8.62 (1H, s) 38) NMR (CDCl 3, δ) 1.00 (9H, s), 1.22 (3H, t, J = 7Hz) ,
2.25 (1H, d, J = 15.3Hz), 2.31 (1H, d, J = 15.3Hz), 3.99-
4.27 (2H, m), 5.81 (1H, d, J = 3Hz), 5.98 (1H, d, J = 3Hz),
7.73-7.81 (2H, m), 8.62 (1H, s) 39) NMR (CDCl ₃ , δ) 1.21 (3H, t, J = 7Hz), 3.98-4.25 (2H,
m), 5.98 (1H, d, J = 3Hz), 6.05 (1H, d, J = 3Hz), 6.47 (1H,
d, J = 15Hz), 7.27-7.45 (5H, m), 7.63-7.71 (2H, m), 7.7
6 (1H, d, J = 15Hz), 8.58 (1H, s) 40) NMR (CDCl 3, δ) 1.22 (3H, t, J = 7Hz), 3.75 (3H, s),
3.98-4.26 (2H, m), 5.73 (1H, d, J = 2Hz), 5.86 (1H, d, J = 2
Hz), 7.72-7.78 (2H, m), 8.60 (1H, s) 41) NMR (CDCl ₃ , δ) 1.22 (3H, t, J = 7Hz), 1.24 (3H, t, J = 7
Hz), 4.11 (2H, m), 5.73 (1H, d, J = 2Hz), 4.22 (2H, q, J = 7
Hz), 5.76 (1H, d, J = 2Hz), 5.83 (1H, d, J = 2Hz), 7.75 (2
H, m), 8.59 (1H, s) 42) NMR (CDCl ₃ , δ) 1.17-1.29 (9H, m), 3.98-4.27 (2H,
m), 5.00 (1H, 7-fold, J = 6Hz), 5.77 (1H, d, J = 2Hz), 5.8
0 (1H, d, J = 2Hz), 7.72-7.79 (2H, m), 8.59 (1H, s) 43) NMR (CDCl ₃ , δ) 1.22 (3H, t, J = 7Hz), 1.45 (9H, s),
3.98-4.26 (2H, m), 5.73 (1H, d, J = 2Hz), 5.78 (1H, d, J = 2
Hz), 7.72-7.78 (2H, m), 8.61 (1H, s) 44) NMR (CDCl ₃ , δ) 1.24 (3H, t, J = 7Hz), 1.44 (9H, s),
4.17 (2H, q, J = 7Hz), 5.78 (2H, s), 7.76 (2H, m), 8.13
(1H, s)

Next, test examples will be described.

Test Example 1 Control Effect on Cotton Aphid Best Guard Granules (1% Granules) (Takeda Pharmaceutical Co., Ltd.)
(1% of 1- [N- (6-chloro-3-pyridylmethyl) -N-ethylamino] -1-methylamino-2-nitroethylene-containing granules). 70 g "was filled in a polypot having a diameter of 6 cm, and cucumber (variety: four leaves) was sown. 15-25 ° C
Irrigation and fertilization in a glass greenhouse to grow seedlings and sowing 3
Three-leaf stage seedlings after one week were planted in a 1/5000 are Wagner pot. As a control, three plots were prepared by mixing the three-leaf seedlings grown in the same manner as above with a planting-treated soil in a 1/5000 are Wagner pot during regular planting. Planting 6 above
Two weeks after the week, one middle leaf was selected from each strain, and 10 adult female aphids were released. Five days later, the number of surviving insects in the leaves to be released was examined. Table 71 shows the test results.

[0175]

[Table 71] 1) Indicates the density index when the density of the untreated area is 100
() Shows the number of surviving insects per leaf. 2) The time of aphid release is indicated in the period after planting. 3) 14.3 g per 1 liter of seedling culture soil (0.1% of active ingredient)
43g). 4) 28.6g per liter of seedling culture (0.2% of active ingredient)
86g).

Test Example 2 Control effect on aphids and thrips Best guard granules (1% granules) (Takeda Pharmaceutical Co., Ltd.)
Alternatively, Admire 1 granule (1% 1- (6-chloro-3-pyridylmethyl) -N-nitro-imidazolidine-2-ylideneamine-containing granule) (Nippon Bayer Agrochem Co., Ltd.) was added per liter. Using the seedling cultivation soil (Sakata seedling cultivation soil) mixed with 1 g or 2 g, the following crops were raised. Fruits and vegetables are filled with the above-mentioned seedling cultivation soil.
The seeds were sowed in a 0-well cell tray, and 15 to 30 days later, they were temporarily planted in a polypot having a diameter of 9 cm using the above-mentioned seedling cultivation soil, and the seedlings were further raised for about 30 days. The leafy vegetables were filled with the above-mentioned seedling culture soil.
The seeds were sown in a well cell tray and raised for about 20 to 25 days.

[0177]

[Table 72]

As a result, there was no phytotoxicity for the two drugs, and a clear control effect on aphids and thrips was observed in all crops as compared with the untreated plots.

Test Example 3 Control effect on peach aphid 2.5 g or 5 g of Best Guard granules per liter or TI-435 granules (Takeda Pharmaceutical Co., Ltd.) (1- (2-chloro-5-thia) Zolylmethyl)
Granules containing 0.5% of -3-methyl-2-nitroguanidine) are 1.25 g or 2.5 g per liter.
g, mixed seedling cultivation soil “Nippi Rina cultivation soil (Nippon Fertilizer Co., Ltd.)” was filled in a 128-well cell tray and seeded with eggplant (variety: 1000 ryo). Irrigation and fertilization were carried out in a glass greenhouse at 15 to 25 ° C. to raise seedlings, and 29 days after sowing, they were tentatively planted in polypots having a diameter of 9 cm. 15 days after sowing, at intervals of one week, 10 winged female peach aphids were released, and 5 days later, the number of surviving insects was examined. Table 73 shows the test results.

[Table 73] 1) The density index is shown when the density of the untreated section is 100. 2) The period after sowing indicates the aphid release time.

[0180]

The present invention relates to a method for controlling pests on angiosperms other than rice, comprising raising seedlings in seedling containers filled with seedling cultivation soil mixed with pesticidal active ingredients before sowing or provisional planting. This is a pest control method characterized by not only raising the seedlings but also having an insecticidal effect even after transplanting in this field, and exhibiting a long-term high control effect with only one treatment. The number of times of chemical treatment can be greatly reduced. In addition, as a work during the off-farm season, it can be treated simultaneously with the mixing of fertilizers and the like as a normal work when preparing soil for raising seedlings. As a result, a great reduction in labor is enabled.

[0181]

[Brief description of the drawings]

FIG. 1 shows a flow chart of a crop cultivation procedure.

────────────────────────────────────────────────── ─── Continued on the front page (51) Int.Cl. ⁶ Identification code FI A01N 43/80 101 A01N 43/80 101 43/84 101 43/84 101 43/90 43/90 47/18 47/18 51 / 00 51/00 55/00 55/00 C C07D 487/04 150 C07D 487/04 150 // C07D 231/38 231/38 B 403/04 231 403/04 231 403/06 207 403/06 207 225 225 231 231 403/12 209 403/12 209 405/04 231 405/04 231 409/06 231 409/06 231 413/04 231 413/04 231 413/06 203 413/06 203 207 207 231 231 231 498/04 521 / 00 521/00 498/04 112Q

Claims (26)

[Claims] 1. A method for controlling insect pests on angiosperms other than rice, comprising raising seedlings in seedling containers filled with seedling cultivation soil mixed with an agricultural chemical active ingredient before sowing or provisional planting. 2. The method according to claim 1, wherein the angiosperm is a dicotyledon or a lily plant. 3. The angiosperm plant is a plant of the order Coleoptera, Rhododendron, Rosaceae, Aceraceae, Camellia, Mallow, Lamiaceae, Cucurbites, Psyllides, Liliaceae, Primrose or Liliaceae. Item 7. The method according to Item 1. 4. An angiosperm plant comprising: Brassicaceae, Acalyptaceae, Papilionidae, Leguminosae, Rosaceae, Apiaceae, Violets, Malvaceae,
2. The method according to claim 1, wherein the method is Solanaceae, Lamiaceae, Cucurbitaceae, Asteraceae, Isopine family, Gentianaceae or Primrose family. 5. The pesticidal active ingredient has the formula: [Wherein, R ^1a represents an alkyl group substituted with a hydrogen atom, a hydrocarbon group, an acyl group or an optionally substituted heterocyclic group, and R ^2a represents a hydrogen atom, a hydrocarbon group, or a group bonded to R ^3a. R ^3a represents a hydrocarbon group, and —SR ^4a (R ^4a represents R ^1a
Is equivalent to ^{), - N (R 5a)} (R 6a) (R 5a and R ^6a are the same or different and represent the same meaning as R ^1a).
Or a divalent group or atom bonded with R ^2a, Y ^a is =
N- or = C ( ^Z1a )-( ^Z1a represents a hydrogen atom or a hydrocarbon group which may be substituted), and ^Xa represents an electron-withdrawing group. Or a salt thereof. (6) R ^1a is (1) a hydrogen atom, (2) a C _1-6 alkyl group, (3) a C _3-10 cycloalkyl group, (4) a C _2-10 alkenyl group, or (5) a C _{2 -10} alkynyl group, (6) _C3-10 cycloalkenyl group, (7) _C6-10 aryl group, (8) _C7-10 aralkyl group,
(9) C _1-4 alkyl - carbonyl group, (10) C _6-10 aryl - carbonyl group, (11) C _1-4 alkylsulfonyl group, or (12) (i) C _1-6 alkyl group, (ii ) A C _2-6 alkenyl group,
(iii) a C _2-6 alkynyl group, (iv) a C _6-10 aryl group, (v)
C _7-9 aralkyl group, (vi) nitro group, (vii) hydroxyl group, (vii
i) mercapto group, (ix) oxo group, (x) thioxo group, (xi)
Cyano group, (xii) carbamoyl group, (xiii) carboxyl group, (xiv) halogen, (xv) C _1-4 alkoxy group, (xvi) C
_1-4 alkylthio group, (xvii) C _1-4 alkylsulfinyl group, (xviii) C _6-10 arylsulfinyl group, (xix) C
_1-4 alkylsulfonyl group, (xx) C _6-10 arylsulfonyl group, (xxi) amino group, (xxii) C _1-6 acylamino group,
(xxiii) a mono- or di-C _1-4 alkylamino group, (xxiv)
It may be substituted with 1 to 5 substituents selected from a C _1-20 acyl group and (xxv) a 3- to 6-membered heterocyclic group or a condensed ring group thereof with a benzene ring or a 3- to 6-membered heterocyclic ring. 3 ~
The method according to claim 5, which is a C _1-3 alkyl group which may be substituted with a 6-membered heterocyclic group or a condensed ring group thereof with a benzene ring or a 3 to 6-membered heterocyclic ring. 7. R ^2a is a hydrogen atom, C _1-6 alkyl groups, C
_3-10 cycloalkyl, C _2-10 alkenyl, C _2-10 alkynyl, C _3-10 cycloalkenyl group, C _6-10 aryl group, C ₁ to bind to C _7-10 aralkyl group, or R ^3a _-Four
An alkylene group, a group represented by —CH ₂ N (Z ^2a ) —CH ₂ — (Z ^2a represents hydrogen, a C _1-6 alkyl group or a C _1-4 alkyl-carbonyl group) or —CH ₂ —O. -CH ₂ - the method of claim 5, wherein. 8. A compound according to claim 1, wherein R ^3a is a C _1-6 alkyl group, a C _3-10 cycloalkyl group, a C _2-10 alkenyl group, a C _2-10 alkynyl group,
C _3-10 cycloalkenyl group, C _6-10 aryl group, C _7-10
Aralkyl group, -SR ^4a [R ^4a is (1) hydrogen atom, (2) C
_1-6 alkyl group, (3) C _3-10 cycloalkyl group, (4) C
_2-10 alkenyl group, (5) C _2-10 alkynyl group, (6) C _3-10
Cycloalkenyl group, (7) C _6-10 aryl group, (8) C _7-10
Aralkyl group, (9) C _1-4 alkyl-carbonyl group, (10)
C _6-10 aryl-carbonyl group, (11) C _1-4 alkylsulfonyl group or (12) (i) C _1-6 alkyl group, (ii) C _2-6
Alkenyl group, (iii) C _2-6 alkynyl group, (iv) C _6-10 aryl group, (v) C _7-9 aralkyl group, (vi) nitro group, (vi
(i) hydroxyl group, (viii) mercapto group, (ix) oxo group, (x) thioxo group, (xi) cyano group, (xii) carbamoyl group, (xii
i) a carboxyl group, (xiv) halogen, (xv) C _1-4 alkoxy group, (xvi) C _1-4 alkylthio group, (xvii) C _1-4 alkylsulfinyl group, (xviii) C _6-10 arylsulfinyl Group, (xix) C _1-4 alkylsulfonyl group, (xx) C _6-10 arylsulfonyl group, (xxi) amino group, (xxii) C _1-6 acylamino group, (xxiii) mono- or di-C _{1 -5} alkylamino groups, (xxiv) a _C1-20 acyl group and (xxv) a 3-6 membered heterocyclic group or a condensed ring group thereof with a benzene ring or a 3-6 membered heterocyclic ring. shows a fused ring group optionally substituted C _1-3 alkyl group optionally substituted 3-6 membered heterocyclic group or its benzene ring or 3-6 membered heterocyclic substituents. A group represented by the formula -N (R
^5a ) (R ^6a ) wherein R ^5a and R ^6a are the same or different,
It has the same meaning as R ^4a . Coupling the base or R ^2a is represented by] -S-, C _1-4 alkylene or -N (Z ^3a)
The method according to claim 5, ^wherein- (Z ^3a represents hydrogen, a C _1-6 alkyl group or a C _1-4 alkyl-carbonyl group). 9. A method according to claim 1, wherein ^Ya is = N- or = C ( ^Z1a )-( ^Z1a
Is a hydrogen atom, (i) a C _1-6 alkyl group, (ii) a C _2-6 alkenyl group, (iii) a C _2-6 alkynyl group, (iv) a C _6-10 aryl group, and (v) a C _{7- 9} aralkyl group, (vi) nitro group, (vii) hydroxyl group, (viii) mercapto group, (ix) oxo group, (x) thioxo group, (xi) cyano group, (xii) carbamoyl group, (xiii) carboxyl group (Xiv) halogen, (xv) C _1-4 alkoxy group,
(xvi) a C _1-4 alkylthio group, (xvii) a C _1-4 alkylsulfinyl group, (xviii) a C _6-10 arylsulfinyl group,
(xix) C _1-4 alkylsulfonyl group, (xx) C _6-10 arylsulfonyl group, (xxi) amino group, (xxii) C _1-6 acylamino group, (xxiii) mono- or di-C _1-4 Alkylamino group,
(xxiv) substituted with 1 to 5 substituents selected from a C _1-20 acyl group and (xxv) a 3- to 6-membered heterocyclic group or a fused ring group thereof with a benzene ring or a 3- to 6-membered heterocyclic ring. C _1-6 alkyl, C _3-10 cycloalkyl, C _2-10
The method according to claim 5, which is an alkenyl group, a _C2-10 alkynyl group, a _C3-10 cycloalkenyl group, a _C6-10 aryl group or a _C7-10 aralkyl group. 10. X ^a is a cyano group, a nitro group, a C _1-4 alkoxy-carbonyl group, a hydroxycarbonyl group, a C _6-10
Aryl-oxycarbonyl group, 3- to 6-membered heterocyclic oxycarbonyl group, C _{1-4 optionally} substituted with halogen
Alkylsulfonyl group, sulfamoyl group, di-C _1-4
The method according to claim 5, which is an alkoxyphosphoryl group, a _C1-4 acyl group optionally substituted with halogen, a _C6-10 arylcarbonyl group, a carbamoyl group or a _C1-4 alkylsulfonylthiocarbamoyl. 11. R ^1a is a hydrogen atom, C _1-6 alkyl, formyl, C _1-4 alkylcarbonyl, C _6-10 arylcarbonyl, C _1-4 alkylsulfonyl, or 5 or be substituted by halogen A C _1-3 alkyl substituted with a 6-membered heterocyclic group, wherein R ^2a is bonded to a hydrogen atom, C _1-6 alkyl, C _1-4 alkylene or R ^3a —CH ₂ —N
(Z ^2a ) —CH ₂ — (Z ^2a represents a hydrogen atom, C _1-6 alkyl or C _1-4 alkylcarbonyl) or —C
H ₂ —O—CH ₂ —, wherein R ^3a is C _1-6 alkyl, —S
-R ^41a (R ^41a is a hydrogen atom, C _1-6 alkyl or C _1-4
Represents alkylcarbonyl. ), -N (R ^51a )
(R ^61a ) (R ^51a and R ^61a are the same or different,
Represents hydrogen or C _1-6 alkyl. ) Or C _1-4 alkylene bonded to R ^2a , —S— or —N (Z ^3a )
- (. Z ^3a is of the same meaning as Z ^2a) is, Y ^a is = N
- or = a CH-, method of claim 5, wherein X ^a is nitro or cyano. 12. The pesticidal active ingredient has the formula: [In the formula, Ar represents an optionally substituted aromatic hydrocarbon group or an optionally substituted aromatic heterocyclic group, and R ^1b represents a hydrogen atom, a halogen atom, nitro, cyano, carboxyl, A hydrocarbon group, a group via a sulfur atom or a compound of the formula (Wherein, X ^1b is a hydrogen atom or a carbon atom, a nitrogen atom, an oxygen atom, a group via a sulfur atom or phosphorus atom, Y ^1b
Represents a hydrogen atom or a group via a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a phosphorus atom, or X
^{When 1b} and Y ^1b are combined, Represents a nitrogen-containing heterocyclic group in which the group represented by may be substituted. R ^2b is a group through a hydrogen atom, a halogen atom or a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a phosphorus atom, and W ^b is a halogen atom or a carbon atom, a nitrogen atom, an oxygen atom, Shows a group via a sulfur atom or a phosphorus atom. Or a salt thereof. 13. Ar is (1) hydroxy, amino, mono-
Or di-C _1-6 alkylamino, C _1-6 alkoxy or a C _1-6 alkyl group optionally substituted with a halogen atom, (2) C _1-6 alkyl or C _1-6 alkanoyl, An amino group which may be di-substituted,
(3) hydroxyl group, (4) carboxyl group, (5) nitro group, (6) SF ₅ , (7) C _1-6 alkoxy group, (8) C _1-6 alkanoyloxy group, (9) cyano group And (10) a C _6-14 aromatic hydrocarbon group or a 5- to 8-membered aromatic heterocyclic group which may be substituted with 1 to 6 substituents selected from halogen atoms, or a C _5-10 cyclic hydrocarbon thereof. The method according to claim 12, which is a condensed ring group with hydrogen or a 5- to 6-membered heterocyclic ring. 14. Ar is a phenyl group substituted by 1 to 5 substituents selected from halogen, C _1-6 alkyl and mono-, di- or tri-halogenated C _1-6 alkyl. 12. The method according to 12. 15. R ^1b is (1) a hydrogen atom, (2) a halogen atom,
(3) nitro group, (4) cyano group, (5) carboxyl group, (6)
(i) nitro, (ii) hydroxy, (iii) oxo, (iv) thioxo, (v) cyano, (vi) carbamoyl, (vii) carboxyl, (viii) _C1-15 acyl group, (ix) sulfo group (X) a halogen atom, (xi) a C _1-14 selected from (a) C _1-6 alkoxy and (b) C _6-14 aryloxy which may be mono-, di- or tri-halogenated. Hydrocarbon oxy group, (x
ii) —S (O) _n ^1b R ^{3b wherein} n ^1b represents 0, 1 or 2;
R ^3b represents a C _1-14 hydrocarbon group selected from C _1-6 alkyl and C _6-14 aryl. (Xiii) amino optionally mono- or di-substituted by C _1-6 alkyl or C _1-6 alkyl-carbonyl, (xiv) mono- or di-substituted by C _1-4 alkyl Hydrazono and (xv) (a) a halogen atom, (b) a C _1-4 alkyl and
(c) 1-5 selected from the group (A) consisting of a 5- or 6-membered heterocyclic group optionally having 1 to 4 substituents selected from mono-, di- or tri-halogenated phenoxy groups.
C _1-20 hydrocarbon group which may be substituted with
(7) —S (O) _n ^4b R ^16b [R ^16b is a C _1-20 hydrocarbon group optionally substituted with 1 to 5 substituents selected from the group (A) or (i) -, Di- or tri-halogenated C _1-20 hydrocarbon group, (ii) C _1-14 hydrocarbonoxy group, (iii) C _1-15 acyl group, (iv) C _{1- 15} acyloxy group, (v) carboxyl group, (vi) carbamoyl group optionally mono- or di-substituted by C _1-4 alkyl, (vii) cyclic aminocarbonyl group, (viii) halogen atom, (ix) Oxo group, (x) amidino group, (xi) imino group optionally substituted with C _1-6 alkyl, (xii) C _1-6 alkyl, carbamoyl or N-mono- or N, N-
Amino group which may be mono- or di-substituted with di-C _1-4 alkyl-carbamoyl, (xiii) 3- to 6-membered cyclic amino group, (xiv) C _1-6 alkanoylamide group, (xv) benzamide , (Xvi) a C _1-3 alkylenedioxy group, (xvii)-
B (OH) ₂ , (xviii) hydroxyl group, (xix) nitro group,
(xx) a cyano group, (xxi) -S (O) _n ^3b R ^{11b wherein} n ^3b represents 0, 1 or 2, and R ^11b represents a hydrogen atom or a C _1-14 hydrocarbon group. And (xxii) 3 to 8 which may be substituted with 1 to 6 substituents selected from the group (B) consisting of a sulfamoyl group which may be mono- or di-substituted with C _1-6 alkyl. Membered heterocyclic group or its C
A condensed ring group with a _5-10 cyclic hydrocarbon or a 5- to 6-membered heterocyclic ring, and n ^4b represents an integer of 0 to 2. Or a group represented by the formula (8): [ ^Wherein X ^1b is (i) a hydrogen atom, and (ii) C _1-20 which may be substituted with 1 to 5 substituents selected from the above group (A).
A hydrocarbon group, (iii) a C _1-24 acyl group _optionally substituted with 1 to 5 substituents selected from the group (A), (iv)
A cyano group, (v) a carbamoyl group optionally substituted with a C _1-20 hydrocarbon group _optionally substituted with 1 to 5 substituents selected from the group (A), and (vi) an amidino group , (Vi
i) a 3- to 8-membered heterocyclic group having a bond at a carbon atom which may be substituted with 1 to 5 substituents selected from the group (A) or a C _5-10 cyclic hydrocarbon or A condensed ring group with a 6-membered heterocycle, (viii) a nitro group, (ix) -NR ^4b R ^5b
[Wherein, R ^4b and R ^5b are each (a) a hydrogen atom, (b) a C _1-20 hydrocarbon group _optionally substituted with 1 to 5 substituents selected from the group (A), (c) C _{1-24 optionally} substituted with 1 to 5 substituents selected from the above group (A)
An acyl group, (d) a carbamoyl group which may be substituted with a C _1-20 hydrocarbon group which may be substituted with 1 to 5 substituents selected from the group (A), and (e) a group (B) 3 to 3 which may be substituted with 1 to 5 substituents selected from
8-membered heterocyclic group or its C _5-10 cyclic hydrocarbon or 5
A condensed ring group with a to 6-membered heterocyclic ring, (f) a hydroxyl group, (g) a C _1-20 hydrocarbon group oxy _optionally substituted with 1 to 5 substituents selected from the above group (A) Group or (h) -S
(O) _n ^2b R ^6b (R ^6b is a hydrogen atom or a C which may be substituted with 1 to 5 substituents selected from the above group (A).
_1-20 hydrocarbon group, and n ^2b represents an integer of 1-2. ). Groups represented by], (x) may be substituted with 1 to 5 substituents selected from the group (B), 3 to 8-membered heterocyclic group or its C ₅ having a bond to a nitrogen atom _-10 cyclic hydrocarbon or a condensed ring group with a 5- to 6-membered heterocyclic ring or (xi) -N ＝ C (R ^7b ) R ^{8b wherein} R ^7b and R ^8b are each a hydrogen atom, selected from the above group (A) A C _1-20 hydrocarbon group _optionally substituted with 1 to 5 substituents, a C _1-20 hydrocarbon _optionally substituted with 1 to 5 substituents selected from the above group (A) Oxy group or -N
R ^9b R ^10b (R ^9b and R ^10b each represent a hydrogen atom, a hydroxyl group or a C _1-20 hydrocarbon group which may be substituted with 1 to 5 substituents selected from the above group (A). A group represented by the formula: (xii) -OR ^{12b wherein} R ^12b is (a) a hydrogen atom, and (b) C _1- which may be substituted by 1 to 5 substituents selected from the above group (A). _{A 20-} hydrocarbon group, (c) a 3- to 8-membered heterocyclic group optionally substituted with 1 to 5 substituents selected from the group (B), or a C _5-10 cyclic hydrocarbon or 5 to 6 member thereof. A condensed ring group with a membered heterocyclic ring, (d) a C _1-24 acyl group _optionally substituted with 1 to 5 substituents selected from the above group (A), and (e) a group from the above group (A) A carbamoyl group optionally substituted with a C _1-20 hydrocarbon group _optionally substituted with 1 to 5 selected substituents, (f) -N
R ^13b R ^14b (wherein, R ^13b and R ^14b are each a hydrogen atom, a C _1-20 hydrocarbon group optionally substituted with 1 to 5 substituents selected from the above group (A), or the above group (B)
A 3- to 8-membered heterocyclic group which may be substituted by 1 to 5 substituents selected from the group consisting of: and a condensed ring group thereof with a _C5-10 cyclic hydrocarbon or a 5- to 6-membered heterocyclic ring. Or a group represented by (g) -SiR ^15b ₃ (R ^15b is a C _1-20 which may be substituted with 1 to 5 substituents selected from the group (A)).
Shows a hydrocarbon group. ). Groups represented by], (xiii) -S (O) n 4b R 16b (R 16b is 1-5 optionally substituted with a substituent C _1-20 hydrocarbon selected from the group (A) Group or a 3- to 8-membered heterocyclic group optionally substituted with 1 to 5 substituents selected from the above group (B) or its condensation with a _C5-10 cyclic hydrocarbon or a 5- to 6-membered heterocyclic ring And n ^4b represents an integer of 0 to 2;
Or (xiv) -PO (OR ^17b ) ₂ (R ^17b
_{Represents a} hydrogen atom or a C _1-15 alkyl group. A group represented by), Y ^1b is either as defined above X ^1b, or Together, with X ^1b and Y ^1b, embedded image May be substituted with 1 to 5 substituents selected from the group (A) and optionally substituted with 1 to 3 C _1-20 hydrocarbon groups or oxo groups. Nitrogen 5
Shows an 8-membered heterocyclic group. A group represented by the formula:
2. The method according to 2. (16) R ^1b is a cyano group or a compound of the formula: [Wherein, X ^1b represents a group represented by —NR ^20b R ^21b (R ^20b and R ^21b each represent a hydrogen atom, hydroxy, C _1-6 alkanoyl or C _1-6 alkyl), and Y ^1b represents hydrogen. Mono-atomic, hydroxyl, C _1-6 alkoxy
Or a C _1-6 alkoxy group which may be di-substituted, a C _1-6 alkanoyloxy group which may be mono-, di- or tri-substituted with a halogen atom, mono- or di-C _1-6 Alkyl-carbamoyloxy group, C
_1-6 alkoxy-carbonyloxy group, C _6-14 aryl-carbonyloxy group optionally substituted with C _1-6 alkyl, formula —NR ^22b R ^23b (wherein, R ^22b and R ^23b are each a hydrogen atom , A C _1-6 alkyl group, a C _1-6 alkanoyl group or a C _1-6 alkoxy-carbonyl group), a C _1-6 alkyl group, or X ^1b and Y ^1b
Together with (R ^24b represents a hydrogen atom or a C _1-6 alkyl group.) 13. A group represented by the formula:
The described method. 17. A C _1-20 hydrocarbon group, wherein R ^2b is (1) a hydrogen atom, and (2) 1 to 5 substituents selected from the group (A) according to claim 15. (3) A C _1-24 acyl group _optionally substituted with 1 to 5 substituents selected from the group (A) according to claim 15, (4) a cyano group, (5) a (15) A carbamoyl group optionally substituted with a _C1-20 hydrocarbon group _optionally substituted with 1 to 5 substituents selected from the group (A), (6) an amidino group, (7) 15. A 3- to 8-membered heterocyclic group having a bond at a carbon atom which may be substituted with 1 to 5 substituents selected from the group (A) described in 15 or a C _5-10 cyclic hydrocarbon or 5- to 5-membered heterocyclic group A condensed ring group with a 6-membered heterocyclic ring, (8) a nitro group, (9) —NR ^4b R ^{5b wherein} R ^4b and R ^5b are each (a) a hydrogen atom, and (b) the group according to claim 15. Selected from (A) To five may be substituted with a substituent C _1-20 hydrocarbon group, (c) according to claim 15
A C _1-24 acyl group which may be substituted with 1 to 5 substituents selected from the group (A) according to claim 15, (d) 1 to 5 C _1-24 acyl groups selected from the group (A) according to claim 15. A carbamoyl group optionally substituted with a C _1-20 hydrocarbon group _optionally substituted with a substituent, (e) substituted with 1 to 5 substituents selected from the group (B) according to claim 15. A 3- to 8-membered heterocyclic group which may be substituted or a condensed ring group thereof with a _C5-10 cyclic hydrocarbon or a 5- to 6-membered heterocyclic ring, (f) a hydroxyl group, and (g).
5. a C _1-20 hydrocarbon group oxy group optionally substituted with 1 to 5 substituents selected from the group (A) of 5 or (h)
_{^{-S (O) n 2b R 6b}} (R 6b is a hydrogen atom or claim 15
A C _1-20 hydrocarbon group _optionally substituted with 1 to 5 substituents selected from the group (A) described above, and n ^2b represents an integer of 1 to 2. ). And (10) a group selected from the group (B) according to claim 15,
A 3- to 8-membered heterocyclic group having a bond at a nitrogen atom or a condensed ring group thereof with a _C5-10 cyclic hydrocarbon or a 5- to 6-membered heterocyclic ring, which may be substituted with five substituents, or 11)
—N ＝ C (R ^7b ) R ^{8b wherein} R ^7b and R ^8b are each a hydrogen atom, and may be C _1- which may be substituted with 1 to 5 substituents selected from the group (A) according to claim 15. ₂₀ hydrocarbon groups, a C _1-20 hydrocarbonoxy group optionally substituted with 1 to 5 substituents selected from the group (A) according to claim 15, or —NR ^9b R ^10b (R ^9b and R ^10b is a hydrogen atom,
A C _1-20 which may be substituted with a hydroxyl group or 1 to 5 substituents selected from the group (A) according to claim 15.
Shows a hydrocarbon group. A group represented by the formula (12) -OR
^12b [R ^12b is (a) a hydrogen atom, (b) a C _1-20 hydrocarbon group _optionally substituted with 1 to 5 substituents selected from the group (A) according to claim 15, (c) A 3- to 8-membered heterocyclic group optionally substituted with 1 to 5 substituents selected from the group (B) according to claim 15, or a _C5-10 cyclic hydrocarbon or a 5- to 6-membered heterocyclic ring thereof. And a fused ring group with (d).
A C _1-24 acyl group which may be substituted with 1 to 5 substituents selected from the group (A) described above, (e) 1 to 5 C _1-24 groups selected from the group (A) according to claim 15, A carbamoyl group optionally substituted with a C _1-20 hydrocarbon group _optionally substituted with a substituent, (f) -NR ^13b R ^14b (wherein, R ^13b and R
^14b is a hydrogen atom, each of which may be substituted by 1 to 5 substituents selected from the group (A) according to claim 15;
_{A 1-20} hydrocarbon group or 3-8 which may be substituted with 1-5 substituents selected from the group (B) according to claim 15.
Membered heterocyclic group or its _C5-10 cyclic hydrocarbon or 5-
A condensed ring group with a 6-membered heterocyclic ring is shown. ) Group or represented by _{^{(g) -SiR 15b 3 (R}} 15b is claim 15 groups according (A)
A C _1-20 hydrocarbon group which may be substituted with 1 to 5 substituents selected from ). ]
And a group represented by the formula: (13) -S (O) _n ^4b R ^16b (R ^16b is a C _{1- optionally} substituted with 1 to 5 substituents selected from the group (A) according to claim 15). ₂₀ hydrocarbon group or claim 15 1-5 3-8 membered optionally substituted with a substituent selected from the group (B) according heterocyclic group or a C _5-10
A fused ring group with a cyclic hydrocarbon or a 5- to 6-membered heterocycle,
n ^4b represents an integer of 0 to 2. ) Or
(14) -PO (OR ^17b ) ₂ (R ^17b is a hydrogen atom or C
_{1-15 represents} an alkyl group. The method according to claim 12, which is a group represented by the formula: 18. During R ^2b is -NR ^25b R ^26b [wherein the R ^25b and R ^26b, respectively (1) a hydrogen atom, (2) C _1-6 alkyl,
(3) C _7-20 aralkyl optionally substituted with benzoyl, (4) mono- or di-C _1-6 alkyl-carbamoyl group, (5) C _1-6 alkanoyl optionally substituted with halogen, (6) C _6-14 arylcarbonyl or (7) C _1-6 alkoxy-carbonyl. ] Group or -N = C (R ^27b) represented in R ^28b [wherein, each R ^27b and R ^28b (1) hydrogen atom, (2) C _1-6 alkyl group, (3) C _1-4 A C _6-14 aryl group optionally substituted with alkoxy and / or hydroxy, (4) a C _1-6 alkoxy group, (5) a mono- or di-C _1-6 alkylamino group or (6) hydroxyamino Represents a group. A group represented by the formula:
2. The method according to 2. 19. W ^b is _{(1) -S (O) n} 5b R 48b [in wherein, n
^5b represents an integer of 0 to 2, and R ^48b represents a C _1-6 alkyl group ^optionally substituted with halogen. A group represented by
(2) C _1-6 alkanoyl group optionally substituted by halogen or C _1-6 alkylthio, or formula (3): [ ^Wherein , X ^2b represents an optionally substituted haloalkyl group, X ^3b represents a hydrogen atom or a group via a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a phosphorus atom, and Y ^2b represents a nitrogen atom, an oxygen atom. Or a group via a sulfur atom or a phosphorus atom, or X ^3b and Y ^2b may form a thioxo group, a hydroxyimino group or an oxirane ring,
R ^2b and Y ^2b each may be substituted with at least one heteroatom selected from an oxygen atom, a nitrogen atom, a sulfur atom or a phosphorus atom, and
_{A 2-4} alkylene group or a C _2-4 alkenylene group may be formed]. 20. X ^2b represents a halo C _1-6 alkyl group, and X ^3b represents
(1) hydrogen atom, or (2) (i) halogen, (ii) hydroxy, (iii) C _1-6 alkylthio group, (iv) C _1-6 alkoxy group, (v) -NR ^29b R ^30b [R ^29b and R ^30b each represent a hydrogen atom, a C _1-6 alkyl group, a C _1-6 alkanoylamino group or a C _7-20 aralkyl group. And (vi) -PO (OR ^31b ) ₂ [R ^31b represents a C _1-6 alkyl group. Or a group represented by (vii) a C _1-6 alkyl group which may be substituted by 1 to 3 substituents selected from a 5- to 6-membered heterocyclic group, wherein Y ^2b is (1) a hydroxyl group, 2)
(i) C _1-6 alkoxy, (ii) C _1-6 alkoxycarbonyl (eg, methoxycarbonyl, ethoxycarbonyl, etc.) or (iii) mono- or di-C _1-6 alkylamino. C _1-6 alkoxy group, (3) C _2-10 alkenyloxy group, (4) C _3-6 cycloalkyloxy group,
(5) a carbamoyloxy group optionally substituted with C _1-6 alkyl or C _6-14 aryl, (6) a C _1-6 alkanoyloxy group optionally substituted with halogen, (7) halogen or C C _{6-14 optionally} substituted with _1-6 alkyl
Aryloxy group, (8) C _1-6 alkoxycarbonyl group, (9) (i) C 1-6 alkyl, (ii) cyano, (iii) halogen or (iv) mono, -, di- - or tri - Halogeno C
_1-6 alkyl optionally substituted C _6-14 aryl-carbonyl group, (10) optionally substituted C _6-14 aryl-oxycarbonyl group nitro, (11) C _1-6
Alkoxycarbonylamino group, (12) benzoyl optionally substituted C _7-20 also be aralkyloxy group, (1
3) Formula [Wherein, R ^32b and R ^33b each represent (i) a C _6-14 aryl group optionally substituted with halogen or (ii) a C _1-6
Shows an alkyl group. A group represented by the formula (14)
(R ^34b ) _{3 wherein} R ^34b represents a C _1-6 alkyl group. ]
And (15) a substituent selected from (i) C _1-6 alkyl, (ii) C _1-6 alkylthio and (iii) oxo.
A 5- or 6-membered heterocyclic-oxy group or a condensed ring group of a 5- or 6-membered heterocyclic ring and a benzene ring,
6) 5 to 6 which may be substituted by 1 to 3 substituents selected from (i) C _1-6 alkyl, (ii) acetylamino, (iii) oxo, (iv) halogen and (v) hydroxy. membered heterocyclic group, or fused ring group and its benzene ring or a 5-6 membered heterocyclic ring, (17) -NR ^35b R ^36b wherein, R ^35b and R ^36b
Each (i) a hydrogen atom, (ii) a hydroxyl group, (iii) cyano, halogen, C _1-6 alkoxycarbonyl or mono- - may be substituted by or di -C _1-6 alkylamino C _1-6 An alkyl group, (iv) a C _6-14 aryl group optionally substituted with 1 to 3 halogens or C _1-6 alkyl, (v) a C _1-6 alkanoyl group optionally substituted with halogen, ( vi) C _1-6 alkoxy group, (vii) C _7-20 aralkyloxy group, (viii) C _1-6 alkoxycarbonyl group, (i
x) a mono- or di-C _1-6 alkylcarbamoyl group,
(x) a C _2-10 alkynyl group, (xi) a C _6-14 arylsulfonyl group optionally substituted with halogen, (xii) a C _1-6 alkylsulfonyl group optionally substituted with halogen,
(xiii) a C _1-6 alkylsulfinyl group optionally substituted with halogen, (xiv) a C _6-14 arylsulfonylamino group _optionally substituted with C _1-6 alkyl, (xv) C _1-6
It represents an alkanoylamino group or (xvi) C _1-6 alkoxycarbonylamino group. A group represented by the formula (18):
ＣＲCR ^37b R ^{38b wherein} R ^37b and R ^38b are each a hydrogen atom, a C _1-6 alkyl group, a C _1-6 alkoxy group or a C _{1-6
6-14 represents an} aryl group. (19) a C _1-6 alkylthio group which may be substituted with halogen or C _1-6 alkoxycarbonyl, (20) a C _6-14 arylthio group, and (21) a compound represented by the formula: Wherein W ^c is O or S, and R ^39b is a group represented by the formula —NR ^40b R ^41b
(Each R ^40b and R ^41b showing a C _1-6 alkyl group.) A group represented by a C _1-6 alkyl group or a C _1-6 alkoxy group. (22) C _6-14 arylsulfonyl group, (23) C _1-6 alkylsulfonyl group,
(24) C _1-6 alkylsulfinyl group, (25) (i) cyano, (i
i) C _1-6 alkoxycarbonyl and (iii) (a) C _6-14 aryl optionally substituted with halogen and / or
(b) a C _1-6 alkyl group optionally substituted with 1 to 3 substituents selected from a carbamoyl group optionally substituted with C _1-6 alkyl, or (26) a formula -PO (R ^42b )
₂ (wherein, R ^42b is. Showing a C _1-6 alkoxy group) a group represented by or R ^2b and Y ^2b and by the formula -Z ^2b -CR ^{43 b,}
R ^44b -NR ^45b-wherein R ^43b , R ^44b and R ^45b are hydrogen or a C _1-6 alkyl group, Z ^2b is an oxygen atom or -NR ^46b- (R ^46b is hydrogen or C _1-6 alkyl Represents a group). A group represented by the formula:
Z ^2b -CR ^47b = N- wherein R ^47b is hydrogen, a C _1-6 alkyl group or an amino group, and Z ^2b is as defined above. A group represented by the formula: -N = CR ^43b -NR ^44b-
(Wherein R ^43b and R ^44b are as defined above), or a group represented by the formula Z ^2b -C (= W ^d ) -NR ^44b-
[Wherein, R ^44b and Z ^2b have the same meaning as described above, and W ^d represents an oxygen atom or a sulfur atom. 20. The method according to claim 19, which represents a group represented by the formula: 21. An agricultural chemical active ingredient comprising (1) 1- [N- (6-chloro-3-pyridylmethyl) -N-ethylamino] -1.
-Methylamino-2-nitroethylene, (2) 1- (2-
Chloro-5-thiazolylmethyl) -3-methyl-2-nitroguanidine, (3) 1- (6-chloro-3-pyridylmethyl) -N-nitro-imidazolidine-2-ylideneamine, (4) N- (6 -Chloro-3-pyridylmethyl)
-N'-cyano-N-methylacetamidine, (5) 1-
(2-chloro-5-thiazolylmethyl) -3,5-dimethyl-2-nitroimino-hexahydro-1,3,5-
Triazine, (6) 1- (3-tetrahydrofuranylmethyl) -3-methyl-2-nitroguanidine, (7) 3-
(2-chloro-5-thiazolylmethyl) -5-methyl-
4-nitroimino-1,3,5-perhydrooxadiazine, (8) 3- (2-chloro-5-pyridylmethyl)-
1,3-thiazolidine-2-ylidenecyanamide or
(9) 5-amino-1- (2,6-dichloro-α, α, α
The process according to claim 1, which is -trifluoro-p-tolyl) -4-trifluoromethylsulfinylpyrazole-3-carbonitrile. 22. The active ingredient of a pesticide according to the formula: Wherein the R ^1c is C _1-6 alkyl or C _1-6 haloalkyl group, a n ^c is 0, 1 or 2, X ^c is -NR ^2c R ^3c,
-N = CHOR ^4c (R ^2c and R ^3c each represent a hydrogen atom or a C _1-6 alkyl group, and R ^4c represents a C _1-6 alkyl group) or -N = CHNR ^6c R ^7c (R ^6c and R ^7c Each represents a hydrogen atom or a C _1-6 alkyl group),
^5c represents an optionally substituted alkyl group or an optionally substituted acyl group], or a salt thereof. 23. The method according to claim 22, wherein R ^5c is an ^optionally substituted carbamoyl group. 24. R ^5c is (1) C _1-6 alkoxy with 1-3 optionally substituted by C _1-6 alkyl groups, substituted by one or two by (2) C _1-6 alkyl Amino, C
_{1-6 with} alkoxy, phenyl or halogen atom
An optionally substituted C _2-10 alkanoyl group, (3) C
_4-10 cycloalkanoyl group, (4) C _3-10 alkenylcarbonyl group optionally substituted by 1 to 2 phenyl,
(5) benzoyl group, (6) C _1-6 alkyl, C _3-9 cycloalkyl, C _2-6 alkenyl, C _2-6 alkynyl, phenyl,
Benzyl, amino optionally substituted by 1 or 2 alkyl with C _1-6 alkyl, cyclic amino, hydroxyl, formyl or carbamoyl optionally substituted by 1 or 2 alkyl with C _1-6 alkoxy, (7) cyclic 23. The method according to claim 22, which is an aminocarbonyl group or a (8) _C1-6 alkoxy-carbonyl group. 25. X ^c is -NH ₂ or -N = CHOR
^{23. wherein} R ^4c is a C _1-6 alkyl group.
The described method. 26. The method according to claim 22, wherein R ^1c is a trifluoromethyl group.