WO2001021618A1 - Acrylonitrile compounds and pest control agent - Google Patents

Abstract

A novel agricultural chemical, especially pesticide; and acrylonitrile compounds represented by formula (1) wherein Q is thiazolyl substituted by a specific group or pyrazolyl substituted by a specific group; A is phenyl optionally substituted by a specific group, naphthyl optionally substituted by a specific group, or a specific heterocyclic group optionally substituted by a specific group; and B is hydrogen, C1-4 alkyl, C1-4 haloalkyl, etc.. The agricultural chemical contains any of the acrylonitrile compounds.

Description

 Description Acrylonitrile compounds and pesticides Technical field

 TECHNICAL FIELD The present invention relates to a novel acrylonitrile compound and an agricultural chemical containing the compound as an active ingredient. The pesticides in the present invention include insecticides, acaricides, nematicides, herbicides, fungicides, and the like, particularly insecticides, acaricides, and nematicides in the fields of agriculture, horticulture, livestock, and sanitation. .

Background art

 Acrylonitrile derivatives have been disclosed in Japanese Patent Application Laid-Open No. 53-92769 as insecticides and in International Patent Application Publications (WO 97/4099, WO 99Z449 9). No. 3, Publication No. WO0Z171933) as a pesticide. Japanese Patent Application Laid-Open No. 60-114452 discloses 2- (4-chlorophenyl) -13- (3-pyridyl) -3-oxopropionitrile as a herbicide. Japanese Patent Application Laid-Open No. 6-111401 discloses the above compounds as fungicides.

 Over the years of use of insecticides and fungicides, pests have recently gained infestation and have become difficult to control with conventional insecticides and fungicides. Some pesticides are highly toxic and some are disturbing ecosystems due to persistence. Therefore, development of new insecticides and fungicides with low toxicity and low residue is always expected.

 In order to solve the above problems, the present inventors have developed a pesticide that exhibits excellent pest control activity at a low dose and has almost no adverse effect on non-target organisms such as mammals, fish and beneficial insects. As a result of continued research, the present inventors have found that the following compounds have high safety and excellent pesticidal activity and completed the present invention.

Disclosure of the invention

That is, the present invention is a compound described in the following [1] to [5] (hereinafter referred to as the present compound) and an agricultural chemical containing the compound as an active ingredient.

[1] Equation (1):

 [Where,

Q is R and (thiazolyl substituted with R Li _n or R and (pyrazolyl substituted with R ,,,,

 Α is phenyl optionally substituted with W, naphthyl optionally substituted with W or heterocyclic group optionally substituted with Y (provided that the heterocyclic group is phenyl, furyl, pyrrolyl, Oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxoxadiazolyl, 1,2,4-oxoxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4 _Triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2 , 4-triazinyl, indazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, quinoxalinyl, phthalazinyl, cinnolinyl or Quinazolinyl.)

B is, H, Ci~C ₄ alkyl, Ct C haloalkyl, C ₂ -C ₄ Arukokishia _{alkyl, CH 3 S CH 2, CH3OC2H4OCH2} , substituted by R ^a a C, -C ₄ alkyl Le, substituted with R ^b C alkyl, tetrahydroviranyl, (CH ₃ ) ₃ Si,

C, ~ (: ₄ alkylsulfonyl, halogen or C, -C ₄ alkyl optionally substituted by phenylalanine sulfonyl, - S_〇 ₂ CF _3, C, _{~C 4} monoalkylamino scan Ruhoniru, C ₂ -C ₈ dialkylaminosulfonyl, phenylalanine aminosulfonyl, C ₂ ~ (: ₅ monoalkylamino Chio carbonyl, C ₃ ~Cg dialkylamino Chio force Ruponiru, C ₂ -C ₅ Shianoarukiru, C ₃ ~ (: ₉ alkoxycarbonylalkyl, one C (= 0) T ', Ρ (= 0) Τ ² Τ ³ , — Ρ (= S) Τ ² Τ ³ , alkali metal atom, alkaline earth metal atom or NHT ⁴ T ⁵ T ^fi ,

R is a heterocyclic group which may be substituted with G (this heterocyclic group is furyl, piperyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxaziazolyl, 1,2,4-Oxazia Zolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3_triazolyl, 1,2,3,4- Tetrazolyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, benzothiazolyl, benzoimidazolyl, indazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, quinoxalinyl, phthalininyl, quinolinyl or quinolinyl is there. )

R ¹ is halogen, CC !. Alkyl, C i Cs alkoxycarbonyl, NO CN, one NU'U ² or —N = CT ⁷ T ⁸ ;

 n is an integer of 0 or 1;

W is halogen, C Ci. Alkyl, ^R: C substituted with ', -C ₄ alkyl, C

_{2 to} C ₆ alkenyl, C _{2 to} C _fi alkynyl,. [~. "Haloalkyl, C2～Ce Ha Roarukeniru, C ₂ -C ₆ haloalkynyl, C ₃ -C s halocycloalkyl, C, -C

Optionally substituted with 1-3 alkyl C ₃ -C 6 cycloalkyl, C, -C ₆ alkoxy.

C2～C ₆ Arukeniruokishi, C2～C ₆ Arukiniruokishi, c, to c ₄ Haroarukoki shea, C -C ₆ haloalkenyl O carboxymethyl, C ₂ -C ₆ haloalkynyl O carboxymethyl, Ci C alkyl sulphates enyl, C, -C ₄ alkylsulfinyl, alkylsulfenyl Honiru, C ₂ ~ (: 6 § Luque Nils Le Hue alkenyl, C ₂ ~ (: 6 alkenylsulfinyl, c ₂ to c ₆ alkenylsulfonyl, c ₂ to c ₆ Arukinirusuru phenyl, alkynylsulfinyl of c ₂ ~c _6, C2~C ₆ alkynylsulfonyl, Ct C Haroaruki Rusurufueniru, C i~C ₄ haloalkylsulfinyl, c, to c ₄ eight Roarukirusu Ruhoniru, c ₂ to c ₆ eight Roarukenirusuru Hue alkenyl, c ₂ to c ₆ halo alkenyl Le Fier, C ₂ -C ₆ haloalkenyl sulfonyl, C2~C ₆ haloalkylene Nils Ruff Eniru, C ₂ -C ₆ halo alkynylsulfinyl, C ₂ to CS haloalkynyl ^{_{sulfonyl, N0 2, CN, -NU'U 2}} , phenoxy, OH, naphthyl, C ₂ -C ₇ alkoxycarbonyl, C ₂ -C ₄ alkoxyalkyl, C ₂ ~ (: ₄ alkylcarbonyl , C ₂ -C 5 alkylcarbonyl O alkoxy, C ₂ -C 5 haloalkylcarbonyl O alkoxy, base may be substituted with X Nzoiru may phenyl optionally substituted by X, it may be substituted by X Pyridyl, phenyl and phenyl optionally substituted with X From 1 to 4 substituents or 5 is formed by an alkylene bound in adjacent substitution positions to 8-membered ring, optionally selected from among N = CT ⁷ T ^8,

Y is a halogen, C, ~ C ,. Alkyl,, ί ^ haloalkyl,! ~ ^ Alkoxy, C ₂ ~Cs Arukeniruokishi, C2~C ₆ Arukiniruokishi, C, ~C ₄ Haroa alkoxy, C2~C ₆ halo alkenyl O carboxymethyl, C2~C ₆ halo alkynyl O carboxy, C! ~ Ji ^ alkyl sulphates enyl, C, -C ₄ alkylsulfinyl, C, -C ₄ alkyl Rusuruhoniru, C2~C ₆ alkenyl Ruff enyl, c ₂ to c _fi alkenylsulfinyl, C2~C ₆ Aruke Nirusuruhoniru, C ₂ -C ₆ alkylene Nils Ruff enyl, C2~ C «alkynylsulfinyl, C2～C ₆ alkynylsulfonyl, c, to c ₄ Haroaru Kirusurufueniru, C! -C ₄ haloalkylsulfinyl,. ^ ~ Ji haloalkyl sulfonyl, C ₂ ~ (: ₆ halo alkenyl Ruff enyl, C2~C ₆ eight Roarukenirusu Rufiniru, C2~ (: 6 haloalkenyl sulfonyl, C ₂ -C ₆ haloalkylene Nils Le phenyl, C2~C ₆ halo alkynylsulfinyl, C ₂ ~ (: 6 haloalkynylsulfonyl, N〇 ₂ , CN, — NU'U ² , OH, C ₂ to (: α alkoxycarbonyl, C ₂ to C ₄ alkoxyalkyl, C ₂ to Cs alkylcarbonyl O alkoxy, c ₂ to c ₅ eight lower Le kills carbonyl O carboxymethyl, C ₃ -C ₇ dialkylamino § iminocarbonyl O carboxymethyl, optionally substitution with X phenyl, and single N = CT ⁷ T ⁸ ( However, each independently T ⁷ and T ⁸ are, H, phenyl, benzyl or C, or a -C ₆ alkyl, 5 to together with the carbon atom to which the T ⁷ and T ⁸ are attached form a 8-membered ring ) Is a 5- to 8-membered ring formed by 1 to 4 substituents arbitrarily selected from or alkylene bonded at adjacent substituent positions;

G is halogen, C ^ Cs alkyl, haloalkyl, C, -C ₄ alkoxy, C, -C ₄ Bruno, Roarukokishi, C, -C ₄ alkyl sulphates enyl, C, -C ₄ Al Kirusurufiniru, C _(~ (: ₄ alkylsulfonyl, C, -C ₄ haloalkyl sulphates Eniru, C i Ca haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, C ₂ -C ₄ alkenyl, C ₂ ~ (: ₄ Haroarukeniru, C ₂ - C ₄ Arukeniruokishi, C 2 ~ C ₄ haloalkenyl O carboxymethyl, C ₂ -C 4 alkenyl Le Hue alkenyl, c ₂ to c ₄ Al Ke Nils sulfinyl, C 2 to C ₄ § Luque sulfonyl sulfonyl, C ₂ ~ (: 4 haloalkenyl Surufueniru, c ₂ to c ₄ halo alkenylsulfinyl, c ₂ to c ₄ haloalkenyl Sulfonyl, C ₂ -C ₄ alkynyl, c ₂ to c ₄ Haroarukieru, c ₂ ~ c ₄ Arukini Ruokishi, c ₂ to c ₄ haloalkynyl O carboxymethyl, c to c ₄ alkyl Nils Le Hue alkenyl, C 2~ (: ₄ alkynylsulfinyl, c ₂ to c ₄ alkynylsulfonyl, c ₂ to c ₄ eight Russia alkylene Nils Ruff enyl, C 2 to C ₄ halo alkynylsulfinyl, c ₂ to c ₄ c b alkynylsulfonyl, N0 _2, CN, formyl, C 1 to 4 arbitrarily selected from _{2 to} C ₆ alkoxycarbonyl, C 2 to C ₄ alkylcarbonyl, c _{2 to} c ₆ haloalkylcarbonyl, c _{2 to} c ₆ alkylcarbonyloxy and —NU′U ² Substituents;

T ¹ is C, to C ₂ . Alkyl, C ₂ -C ₆ alkenyl, , Mouth alkyl, C _2- (: ₅ alkoxyalkyl, C ₃ -C ₆ halocycloalkyl, d substituted with ^Ra

-C ₄ alkyl, C i Cs alkyl optionally substituted C ₃ ~Ce cycloalkyl Le, C ₃ -C _fi cycloalkyl substituted with R ^a, R ^a and C, is replacement with -C ₄ alkyl cyclopropyl, R ^c and halogen substituted C ₃ -C ₄ cycloalkyl Le, R ^d and C! CA alkyl substituted cyclopropyl, C ₂ -C ₄ alkenyl substituted with R ^a, C t C alkoxy, C, -C ₄ haloalkoxy, C ₂ -C

₅ alkenyloxy, which may be substituted with C 3 -C 3 alkyl, C 3-(: ₆ cycloalkoxy, benzyloxy, C ₂ -C ₅ alkoxycarbonyl, 1 NU'U ² , phenylamino, Z Optionally substituted phenyl, phenyl optionally substituted with Z, phenylthio optionally substituted with Z, naphthyl optionally substituted with Z or 5- or 6-membered optionally substituted with Z Heterocyclic group of the ring (However, these heterocyclic groups are phenyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-year-old oxadiazolyl, 1,2,4- Oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl , 1,2,3,4-tetrazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl and 1,2,4-triazinyl).

T ² and T ³ are each independently 〇_H, phenyl, C, -C ₆ alkyl, C! CB § alkoxy or C i~C ₄ alkyl sulphates enyl, T ⁴ , T ⁵ and T ⁶ each independently represent H, (^ to (; alkyl, C! Ce alkenyl, C _{3 to} C ₃ alkyl which may be substituted by C ₃ to C ₃ alkyl, Or two of T ⁴ , Τ ⁵ and Τ ⁶ may contain an oxygen, nitrogen or sulfur atom together with the nitrogen atom to which they are attached 5 or 8 Forming a membered ring group,

X and Zeta, each independently halogen, Ci Ca alkyl, Ci Ca Haroaru kill, C, -C ₄ alkoxy, C I～C ₄ haloalkoxy, Ji, ~ (: ₄ Arukirusurufu Eniru, C, ~ (: ₄ alkylsulfinyl, C, -C ₄ alkylsulfonyl, C ₂ -C

₅ § Luque Nils Ruff enyl, c ₂ to c ₅ § Luque Nils sulfinyl, c ₂ to c ₅ alkenyl Rusuruhoniru, C! -C ₄ eight-necked alkyl sulphates enyl, C i~C ₄ haloalkylsulfenyl Finiru, C! ~ C ₄ haloalkylsulfonyl, NO ₂ , CN, CH〇, OH, — 1 to 5 substituents arbitrarily selected from NU′U ² , phenyl, phenoxy and C _{2 to} C ₅ alkoxycarbonyl ,

T ⁷ and T ⁸ are each independently H, phenyl, benzyl or C i Ce alkyl, or may form a 5- to 8-membered ring with the carbon atom to which T ⁷ and T ⁸ are bonded. Often,

U ′ and U ² are each independently H, Ci Ce alkyl, C _{2 to} C ₅ alkylcarbonyl, C _{2 to} C ₅ alkoxycarbonyl, phenyl or benzyl, or U ¹ and U ² are bonded to each other. May form a 5- to 8-membered ring with the carbon atoms

R ^a is phenyl optionally substituted with one or more selected from halogen and C i-C ₄ alkyl,

R ^b is optionally substituted with one or more selected from Parogen and C! -C ₄ alkyl

R or a halogen and C I～C may phenyl optionally substituted with one or more members selected from ₄ alkoxy,

R ^d is an acrylonitrile compound represented by the formula: C2 to (: ₄ alkenyl, which may be substituted with halogen.).

[2] The acrylonitrile conjugate according to [1], wherein Q is thiazolyl substituted with R. [3] The acrylonitrile compound according to [1], wherein Q is pyrazolyl substituted with R.

 [4] The acrylonitrile compound according to [1], wherein the scale is pyrimidinyl or birazinyl optionally substituted with G.

 [5] An agricultural chemical comprising at least one of the acrylonitrile compounds according to [1] to [4] as an active ingredient. One C (CN) = C (OB)-part of the compound (1) of the present invention has two isomers, E-form and Z-form, both of which are included in the present invention.

When the substituent B in the formula (1) is a hydrogen atom, the compound of the present invention has the formula

It will be understood that it may exist in tautomeric forms represented by _(1. ) _{(2) (1} ·), wherein E represents CN. The compound is thought to exist predominantly in the enol form (1 '), but may under certain conditions take the tautomeric form (2). It is to be understood that the present invention encompasses all three tautomeric forms and mixtures thereof.

Then Q, A, will be described B, G, R, RY, W, X, Z, and ^{TT 2, TTT 5, TT 7} , T 8, the preferred range of U ¹ and U ^2.

However, the following heterocyclic groups in AI to AIV, RI to RIII, and Τ to T′111 represent the following meanings. Chenyl is thiophen-12-yl or thiophen-13-yl; frills are furan-12-yl or furan-13-yl; pyrrolyl is pyrrole-1-yl, pyrrole. — 2-yl, pyrrol-3-yl, oxazolyl is oxazolyl 2-yl, oxazole _ 4 _yl or oxazolyl 5-yl, and thiazolyl is thiazolyl 2 —Yl, thiazolyl—4-yl or thiazol-5-yl, imidazolyl is imidazoyl-11-yl, imidazole-2-yl or imidazole-41-yl, and isoxazolyl isoxazole — 3-yl, isoxazole— 4-yl or isoxazolyl 5-yl, isothiazolyl is isothiazole-3 4-yl or isothiazole-5-yl or pyrazolyl is pyrazole-11-yl, pyrazole-3-yl, pyrazol-4-yl or pyrazole-5-yl. , 1,3,4 oxadiazolyl is 1,3,4 oxadiazol-2-yl, 1,3,4-thiadiazolyl is 1,3,4-thiadiazol-2-yl, 1,2 , 4Ioxaziazolyl is 1,2,4_oxadiazolyl 3-yl or 1,2,4-oxadiazolyl 5-yl, 1,2,4-thiadiazolyl is 1,2,4-thiadiazole — 3-yl or 1,2,4-thiadiazole_5-yl; 1,2,4-triazolyl is 1,2,4-triazolyl_1-yl, 1,2,4 —Triazole— 3—yl or 1,2,4-triazole—4—yl, 1, 2, 3—thia A Zoriru 1, 2, 3-thiadiazole one route 4 Iru or 1, 2, 3-thiadiazole is one rule 5 I le,

 1,2,3-Triazolyl is 1,2,3-triazole_1-yl, 1,2,3-triazoyl-2-yl or 1,2,3-triazolyl-4-yl 1,2,3,4-tetrazolyl is 1,2,3,4-tetrazol-1-yl, 1,2,3,4-tetrazol-2-yl or 1,2,3,4 —Tetrazoyl 5-yl, pyridyl is pyridine-12-yl, pyridine-3-yl or pyridin-14-yl, and pyrimidinyl is pyrimidine 1-2-yl, pyrimidine 1-4-yl or pyrimidine One 5-yl, pyrazinyl is pyrazine-2-yl, pyridazinyl is pyridazine-3-yl or pyridazine-14-yl, 1,3,5-triazinyl is 1,3 , 5-triazine-2-yl, 1,2,4-triazinyl is 1,2,4-triazine-1-yl, 1,2 4- triazine Hmm 5- I le or 1, 2, 4-triazine - is 6-I le.

 Preferred ranges of A are the following groups.

 AI: phenyl, phenyl, fenyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, pyrazolyl, imidazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,2,3-thiadiazolyl, pyridyl , Pyrimidinyl, pyrazinyl and pyridazinyl.

ΑΠ: phenyl, thiazolyl, pyrazolyl, pyridyl and pyrimidinyl. AI II: thiazolyl, pyrazolyl and pyridyl.

 A IV: Thiazolyl. AV: Pyrazolyl. AVI: Pyridyl.

 Preferred ranges of B are the following groups.

That, BI:! H, C CA alkyl, Ci C haloalkyl, C ₂ -C ₄ alkoxy Shiarukiru, CH ₃ 〇_C ₂ H ₄ 〇_CH _2, C ~ Ji Tewi alkylsulfonyl, halogen Contact and C, -C ₄ alkyl Phenylsulfonyl optionally substituted by one or more selected from — S 選 ば₂ CF ₃ , C _{2 to} C ₈ dialkylaminosulfonyl, C ₃ to (: ₉ -dialkylaminothiocarbonyl, C _{3 to} C ₉ Alkoxycarbonylalkyl, 1 C

(= 〇) D — P (= 0) T ² T ³ , — Ρ (= S) T ² T \ Alkali metal atom, alkaline earth metal atom and ΝΗΤ ⁴ Τ ⁵ Τ ⁶ .

ΒΠ: Η, C, to C ₄ alkyl, C i to C ₄ haloalkyl, C ₂ to (: ₄ alkoxyalkyl, CH ₃ OC ₂ H ₄ OCH2, C i to C ₄ alkylsulfonyl, one S〇 ₂ CF ₃ , One C (= 0) T alkali metal atom, alkaline earth metal atom and ΝΗΤ ⁴ Τ ⁵ Τ

6

ΒΙΠ: Η, C ₂ -C ₄ alkoxyalkyl, C! -C ₄ alkylsulfonyl, — S

〇 ₂ CF ₃ , — C (= 0) T Alkali metal atom, alkaline earth metal atom, and Ν τ-cho 4 s τ ⁶

Β IV: C _{2 to} C ₄ alkoxyalkyl, C, to C ₄ alkylsulfonyl, — S〇 ₂ CF ₃ , — C (= 0) T ^l , alkali metal atom, alkaline earth metal atom and ΝΗΤ

4 5 fi The preferred range of G is each group shown below.

GI: halogen, C! -C _R alkyl, C-C ₄ alkenyl, C ₂ -C ₄ alkynyl, C, -C ₄ haloalkyl, C ₂ -C ₄ haloalkenyl, C ₂ -C ₄ haloalkynyl, C Cs alkyl optionally substituted C ₃ even though -C ₆ cycloalkyl, C, ~ c ₆ alkoxy, c ₂ to c ₄ Arukeniruokishi, c ₂ to c ₄ Arukiniruokishi, c, ~

C ₄ haloalkoxy, ~ (: 4 haloalkenyloxy, C _2- (: 4 haloalkynyloxy, Ci to C ₄ alkylsulfenyl, c, to c ₄ alkylsulfinyl, c, to c

4 alkylsulfonyl, C ₃ -C ₄ alkenyl Le Hue alkenyl, C ₃ ~ (: 4 Arukenirusu Rufiniru, _{c: i} to c ₄ alkenylsulfonyl, c ₃ to c ₄ alkyl Nils Le Hue sulfonyl, c ₃ to c ₄ alkynylsulfinyl, c ₃ to c ₄ alkynylsulfonyl, c, to c ₄ c port alkyl sulphates enyl, C! ~ Ji ^ haloalkylsulfinyl, C, ~ (: 4 Haroa alkylsulfonyl, c ₃ to c ₄ eight b alkenyl Ruff enyl, c ₃ to c ₄ Haroaruke Nils sulfinyl, C ₃ -C ₄ haloalkenyl sulfonyl, C ₃ - ( : ₄ Haroarukini Rusurufueniru, c ₃ to c ₄ halo alkynylsulfinyl, c ₃ to c, Roarukini Rusuruhoniru, N_〇 ^_2, CN, -NU'U _2, halogen or C CA alkyl optionally substituted phenyl! substituted methoxy, C ₂ -C ₆ Arukokishikaru Boniru, c ₂ to c ₄ alkoxyalkyl, c ₂ to c ₄ alkylcarbonyl, c ₂ to c ₄ haloalkylcarbonyl, c ₂ to c ₅ alkylcarbonyl O alkoxy, c ₂ to c ₅ Haroa Le kills carbonyl O carboxymethyl, C ₃ -C ₇ dialkylamino § iminocarbonyl O carboxymethyl, phenyl which may be replacement by Z, may off be substituted with Z A substituent arbitrarily selected from nonoxy, benzoyl optionally substituted with Z, pyridyl optionally substituted with Z, and pyridyloxy optionally substituted with Z (provided that the substituent is 2 And the number of the substituents may be the same or different from each other.), And the number of the substituents is 1, 2, 3, or 4, or is formed by alkylene bonded at adjacent substituent positions. Five-, six-, seven-, or eight-membered rings.

GII:: halogen, C, -C ₆ alkyl, (^ - (^ alkoxy, C, -C ₄ alkyl Rusurufueniru, C, -C ₄ alkyl sulfides El, C, ~ C ₄ alkylsulfonyl, N0 _2, -NU ^L U \ C ₂ -C ₆ alkoxycarbonyl, C 2-(: ₅ alkylcarboxy, C ₃ -C ₇ dialkylaminocarbonyloxy and phenyl optionally substituted with Z (provided that two or more substituents are present) In the case of, they may be the same or different from each other.), And the number of the substituents is 1 or 2.

GIII: halogen,. [~ (^ Alkyl, N_rei_2 one NU'U ² and optionally selected substituents from good phenyl optionally substituted by Z (provided that either the same if the substituent is on two or more And the number of the substituents is 1.

 Preferred ranges of R are the following groups.

That is, RI: furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxaziazolyl, 1,2,4-oxadizazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1 , 2,3,4-tetrazolyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, benzothiazolyl, benzimidazolyl, indazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, quinoxalinyl, , Cinnolinyl or quinazolinyl.

 RII: furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, villazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1 , 2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3_triazolyl, 1,2,3,4-tetrazolyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1, 2, 4-triazinyl.

 RIII: pyrimidinyl, pyrazinyl.

Preferred ranges of R ¹ are the following groups.

That, R: halogen, (:!.! ~ Ji, alkyl, C Cs alkoxycarbonyl, N0 _2, CN, one ^{NU, - N = CT 7 T} 8 0

RI: Halogen, Ci C !. Alkyl, C i~C ₅ alkoxycarbonyl.

 The preferred range of n is nl: 0 or 1, and nil: 0.

 Preferred ranges of Y are the following groups.

That is, YI: halogen, C ′ Ce alkyl, C, to C ₄ haloalkyl, (^ to (^ alkoxy, C _{2 to} C ₄ alkenyloxy, C ₂ to (: ₄ alkynyloxy, C, to C ₄ eight Roarukokishi, C ₂ -C ₄ haloalkenyl O carboxymethyl, C ₂ -C ₄ haloalkynyl O carboxymethyl, C, -C ₄ alkyl sulphates enyl, C i~C ₄ alkylsulfinyl, C, -C ₄ Al alkylsulfonyl , C 3~ (: 4 alkenyl Le Hue alkenyl, C ₃ -C ₄ Arukenirusurufu Iniru, C ₃ -C ₄ § Luque sulfonyl sulfonyl, C ₃ -C ₄ alkylene Nils Ruff enyl, C

3 to (: 4 alkynylsulfinyl, C _{3 to} C ₄ alkynylsulfonyl, 〇, to 〇, □ alkylsulfenyl, C, to (: ₄ haloalkylsulfinyl, Ci to C ₄ haloalkylsulfonyl, C _{3 to} C ₄ halo Alkenylsulfenyl, C:, ~ c ₄ haloalkene Rusurufiniru, C. 3 to (: 4 eight B alkenylsulfonyl, C ₃ -C ₄ haloalkynyl Surufueniru, C ₃ -C ₄ halo alkynylsulfinyl, c ₃ to c ₄ haloalkynyl sulfonyl, N_〇 _2, CN, -NU ' U ² , C _2- (: 4 alkoxycarbonyl, C 2 -C ₄ alkoxyalkyl, C ₂ -C ₄ alkylcarbonyloxy, C ₂ -C ₄ haloalkylcarbonylcarbonyl or phenyl optionally substituted with X Is a substituent arbitrarily selected from the following (however, when the number of the substituents is two or more, they may be the same or different from each other), and the number of the substituents is 1, 2 or 3 .

Y1i: halogen, Ci~C ₄ alkyl, C, -C ₄ haloalkyl, C, -C ₄ alkoxy, C, -C ₄ alkyl sulphates enyl, C, -C ₄ alkylsulfinyl, C, -C ₄ alkylsulfonyl , C ₁ -C ₄ haloalkylsulfenyl phenylalanine, Ci～C ₄ Haroaruki Rusurufiniru, C, ~ (: ₄ haloalkylsulfonyl, N_rei_2, CN, optionally substituted with C 2 to C ₄ alkoxide aryloxycarbonyl or X A substituent arbitrarily selected from the group consisting of phenyl and phenyl. (However, when the number of the substituents is two or more, they may be the same or different.) The number of the substituents is 1, 2 or There are three.

 The number of Y varies depending on the type of heterocyclic ring substituted by Y, and the heterocyclic ring is 1,3,4-isoxaziazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl In the case of 1,2,3-thiadiazolyl or 1,2,3,4-tetrazolyl, the number of Y is 0 or 1, and preferably 1. The heterocycle is thiazolyl, oxazolyl, isoxazolyl, isothiazolyl, 1,3,4-triazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,3,5-triazinyl, 1,2, In the case of 4-triazinyl or 1,2,4-triazinyl, the number of Y is an integer from 0 to 2, preferably 1 or 2. When the heterocyclic ring is phenyl, furyl, pyrazolyl, imidazolyl, pyrimidinyl, virazinyl or pyridazinyl, the number of Y is an integer of 0 to 3, preferably an integer of 0 to 2, more preferably 1 or 2. It is. When the heterocyclic ring is pyrrolyl or pyridyl, the number of Y is an integer of 0 to 4, preferably an integer of 0 to 3, and more preferably 1 or 2.

 Preferred ranges of W are the following groups.

That is, WI: halogen, di, ~ (: ₆ alkyl, CiC haloalkyl, Ci ~ (: ₄ Alkoxy, C i~C ₄ haloalkoxy, c! To c ₄ alkylsulfamoyl phenylalanine, c, to c ₄ alkylsulfide El, C alkylsulfonyl, C i C Haroarukirusu Rufue alkenyl, C i C haloalkylsulfinyl, c, to c ₄ haloalkylsulfonyl, c ₃ to c ₄ Arukeniruokishi, c ₃ to c ₄ haloalkenyl O carboxymethyl, _c: i ~c ₄ § Rukenirusurufue alkenyl, c ₃ to c ₄ alkenylsulfinyl el, _c: i ~ c ₄ alkenyl sulfonyl, C 3 to C ₄ eight b alkenyl Le Hue alkenyl, C ₃ ~ (: 4 halo alkenyl Rufiniru, c ₃ to c ₄ haloalkenyl sulfonyl, c ₃ to c ₄ Arukiniruokishi, c ₃ ~ c ₄ alkyl Nils Ruff enyl, c ₃ to c ₄ alkynylsulfinyl, c ₃ to c ₄ alkynylsulfonyl, N_〇 _2, CN, C _{2 ~C 4} alkoxycarbonyl, C ₂ -C ₄ alkylcarbonyl, C ₂ -C ₄ Haloalkyl Carbonyl, a substituent optionally selected from C 2 to C ₄ alkylcarbonyloxy and —NITU ² (provided that the substituent is

In the case of two or more, they may be the same or different from each other. ) Wherein the number of the substituents is

One, two, three or four.

WII:. Halogen, C C alkyl, CL CA haloalkyl, c, to c ₄ alkoxy, C] -C ₄ haloalkoxy, C

Alkyl sulphates enyl, C! CA Al Kirusurufiniru, C, -C ₄ alkylsulfonyl, C i~C ₄ haloalkyl sulphates Eniru, c, to c ₄ haloalkylsulfinyl, c ₁ to c ₄ haloalkylsulfonyl,

C ₃ -C ₄ Arukeniruokishi, C ₃ -C ₄ haloalkenyl O carboxymethyl, C 3 to C ₄ alkenyl Rusurufueniru, C ₃ -C ₄ alkenylsulfinyl, C ₃ ~ (^ Arukenirusuruho nil, c ₃ to c ₄ alkynyl Oxy, c ₃ -c ₄ alkynylsulfenyl, c ₃ -c ₄ alkynylsulfinyl, C _3- (: ₄ alkynylsulfonyl, N〇2, CN, a substituent arbitrarily selected from When the number of the substituents is two or more, they may be the same or different from each other.), And the number of the substituents is 1, 2 or 3.

win:! halogen, C ~C ₄ alkyl, C, ~C ₄ haloalkyl, (^ ~ (:! ₄ alkoxycarbonyl, c, ~c ₄ haloalkoxy, c, ~c ₄ alkyl sulphates enyl, Ji-Ji Wiaru Kirusurufiniru, c, to c ₄ alkylsulfonyl, c, to c ₄ haloalkyl sulphates Eniru, c, to c ₄ haloalkylsulfinyl, c _t to c ₄ haloalkylsulfonyl,

N0 _2, CN, optionally selected substituents from among (provided that if the substituent is two or more may be different in the same or another.) Comprising the number of the substituents is 1 or 2 pieces It is.

Preferred T ¹ range is the group shown below.

That is, Τ′Ι: C] to C ₁₈ alkyl, C _{2 to} C ₆ alkenyl,,. , Mouth alkyl, C, -C ₄ alkoxy one C I～C ₄ alkyl, have been C> ~ substituted in good phenyl optionally substituted by halogen or C I～C ₄ alkyl (: ₄ alkyl, c ₃ to c ₆ Haroshi black alkyl, C i Cs alkyl optionally substituted c ₃ to c ₆ cycloalkyl Le, halogen or C, -C 4 C ₃ substituted by which may phenyl substituted with alkyl -C ₆ cycloalkyl alkyl, halogen or C i~C ₄ alkyl C ₂ ~ C ₄ alkenyl substituted with optionally phenyl substituted, C i~C,. alkoxy, c, to c ₄ haloalkoxy, c ₃ to c ₅ Arukeniruokishi, c, to c ₃ alkyl optionally substituted with c ₃ to c _fi cycloalkoxy, Benjiruokishi, c ₂ to c ₅ alkoxycarbonyl, - NL U ² Z may be substituted with phenyl, Hue which may be replaced by Z Xy, phenylthio optionally substituted with Z, naphthyl or heterocyclic group optionally substituted with Z (however, this heterocyclic group is phenyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, pyrazolyl, 1,2,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3— It is selected from thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl or 1,2,4-triazinyl. ).

Ding ^:! ~ J ^ alkyl, C ₂ ~ C _fi alkenyl, C, ~ C ₄ haloalkyl, C

2 (: 4 alkoxyalkyl, halogen or C, -C 4 alkyl substituted C in good phenyl substituted, -C ₄ alkyl, C i Cs alkyl optionally C 3 to C be substituted by C3- (substituted with 6-cycloalkyl, halogen or phenyl which may be substituted with Ci-C4alkyl, may be substituted with 6-cycloalkyl, halogen or C, -C4alkyl C ₂ -C 4 alkenyl substituted with good phenyl, Ci C,. alkoxy, C, ~ (: ₄ haloalkoxy, C ₃ -C 5 alkenyl Ruokishi, c ₃ to c ₆ cycloalkoxy, Benjiruokishi, c ₂ to c ₅ alkoxy power Rubonyl, phenyl optionally substituted with Z, phenoxy optionally substituted with Z, phenylthio, naphthyl or heterocyclic group optionally substituted with Z (however, this heterocyclic group is , Frill, oxazolyl, thiazolyl, pyrazolyl or pyridyl.)

Τ'ΙΙΙ: C, ~C ₁₇ alkyl, C ₂ -C 6 alkenyl, (:, ~ (: ₄ haloalkyl, C

2 to C ₄ alkoxyalkyl alkyl, C substituted with phenyl, -C ₄ alkyl, C! Ca alkyl substituted by C3～C 6 optionally cycloalkyl, cycloalkyl substituted by phenyl, substituted with phenyl C ₂ -C ₄ alkenyl, C ^ Cs alkoxy, C i~C ₄ Nono Roarukokishi, c ₃ to c ₅ Arukeniruokishi, _c: i to c ₆ Shikuroa alkoxy, Benjiruokishi, C ₂ -C 5 alkoxycarbonyl, Phenyl optionally substituted with Z; phenoxy optionally substituted with Z; phenylthio, naphthyl; and pyrazolyl or pyridyl optionally substituted with Z.

The preferred range of T ² are a group shown below.

That is, T ² I: phenyl, C, to C ₄ alkyl, C i to C ₄ alkoxy or c! To c

4-alkylsulfenyl.

The preferred range of T ³ is the following groups.

That is, T ³ I: phenyl, Ο, Βalkyl, C, ~ 6 alkoxy or c! ~ C

4-alkylsulfenyl.

The preferred range of T ⁴ is a group shown below.

^{That, T 4 I: H, C} , ~C 4 alkyl, or a C ₃ ~ C _fi cycloalkyl or base Njiru, or T ^4, 2 pieces of T ⁵ and T ⁶ are coupled respectively It forms a 5-, 6- or 7-membered ring which may contain an oxygen, nitrogen or sulfur atom together with the nitrogen atom.

Preferred T ⁵ of the range is the following group.

^{That, T 5 I: H, Ci~} (: 4 alkyl, or a C ₃ ~ C ₆ cycloalkyl or base Njiru, or T ^4, 2 pieces of T ⁵ and T ^fi are each bonded to It forms a 5-, 6- or 7-membered ring which may contain an oxygen, nitrogen or sulfur atom together with the nitrogen atom.

The preferred range of T ⁶ is the following groups. That is, T ⁶ I: H, C! CA alkyl, C ₃ -CH cycloalkyl or benzyl, or two of T ⁴ , Τ ⁵ and T ^FI are bonded to each other. Forms a 5-, 6-, or 7-membered ring that may contain an oxygen, nitrogen, or sulfur atom with the atom;

 Preferred ranges of X are the following groups.

In other words, XI:.! Halogen, (^ ~ (^ alkyl, C 'C haloalkyl, Ji, ~ § alkoxy, C ~C ₄ haloalkoxy, C, ~C ₄ alkyl sulphates enyl, C, ~C ₄ alkyl sulfates Fier, C, -C ₄ alkylsulfonyl, C ₃ ~ (: ₅ Arukenirusuru phenyl, C ₃ -C _S alkenylsulfinyl, C ₃ -C ₅ alkenylsulfonyl, C, -C ₄ haloalkylsulfenyl phenylalanine, C, -C ₄ haloalkylsulfinyl, C ι~ C ₄ haloalkylsulfonyl, N0 _2, CN, one NU 'U ² or C ₂ ~ (: 5 an alkoxy optionally selected substituents from the carbonyl (provided that the substituent is two In the above cases, they may be the same or different from each other.), And the number of the substituents is 1, 2, or 3.

XII:! Halogen, alkyl, C i~C ₄ haloalkyl, C, -C ₄ alkoxy, C, -C ₄ haloalkoxy, C, -C ₄ alkyl sulphates enyl, C i C Al Kirusurufiniru, C -C ₄ alkylsulfonyl, C ₃ -C ₅ alkenyl Le Hue sulfonyl, C! -C ₄ haloalkylsulfenyl phenylalanine, C T～C ₄ haloalkylsulfinyl, C, -C ₄ haloalkylsulfonyl, chosen arbitrarily from among N_〇 ₂ Substituents (however, when the number of the substituents is two or more, they may be the same or different from each other), and the number of the substituents is 1, 2, or 3.

XIII: halogen, C, -C ₄ alkyl, C, -C ₄ haloalkyl, C i C alkoxy, substituent (provided that the same or if the substituent is two or more mutually selected arbitrarily from among And the number of the substituents is one or two.

The number of X differs depending on the ring substituted by X. When the ring is phenyl, the number of X is an integer of 0 to 5, preferably an integer of 0 to 3. When the ring is pyridyl, the number of X is an integer of 0 to 4, preferably 0, 1 or 2, and more preferably 0 or 1. In the case of phenyl, the number of X is an integer of 0 to 3, preferably 0 or 1. Preferred ranges of Z are the following groups.

That, ZI: halogen, alkyl, C, -C ₄ haloalkyl, C, -C ₄ 7 alkoxy, C '-C ₄ haloalkoxy, C i~C ₄ alkylsulfinyl phenylalanine, c, to c ₄ alkylsulfinyl, c , to c ₄ alkylsulfonyl, c ₃ to c ₅ Arukenirusuru phenyl, c ₃ to c ₅ alkenylsulfinyl, c ₃ to c ₅ alkenylsulfonyl, C, ～〇 ₄ haloalkylsulfenyl phenylalanine, C i~C ₄ haloalkylsulfinyl, c , To C ₄ haloalkylsulfonyl, NO CN, one NU'U ² or C ^{2 to} C ₅ alkoxycarbonyl arbitrarily selected substituents (however, when two or more substituents are the same or And the number of the substituents is 1, 2, 3 or 4.

ZII:! Halogen, Ct C alkyl, Ci~C ₄ haloalkyl, Ci~C ₄ alkoxy, C -C ₄ haloalkoxy, C i~C ₄ alkyl sulphates enyl, C ₁ -C ₄ al Kirusurufiniru, c, to c ₄ alkylsulfonyl, c ₃ to c ₅ alkenyl Le Hue sulfonyl, c ₃ to c ₅ alkenylsulfinyl, c ₃ to c ₅ § Luque sulfonyl sulfonyl, c, ~ haloalkylsulfenyl phenylalanine, C! -C ₄ haloalkylsulfinyl, c, to c ₄ substituents which are arbitrarily selected from 8-alkylsulfonyl (however, when the number of substituents is two or more, they may be the same or different from each other), and the number of the substituents Is 1, 2, 3 or 4.

The number of Z differs depending on the type of ring substituted by Z. When the ring substituted by Z is phenyl, the number of Z is an integer of 0 to 5, preferably an integer of 0 to 4, and More preferably, it is 0, 1, 2 or 3. When the ring substituted by Z is naphthyl, the number of Z is an integer of 0 to 7, preferably 0. When the ring substituted by Z is a heterocyclic group, the number of Z differs depending on the heterocyclic ring, and the heterocyclic ring is 1,3,4-oxdiazolyl, 1,2,4-oxdiazolyl, 1,3,4-thiadiazolyl. , 1,2,4-thiadiazolyl, 1,2,3-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,3,4-tetrazolyl or 1,2,3,5-tetrazolyl The number is 0 or 1. The heterocycle is thiazolyl, oxazolyl, isoxazolyl, isothiazolyl, 1,3,4-triazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,3,5-triazinyl, 1,2, 4 In the case of mono-triazinyl or 1,2,4-triazinyl, the number of Z is an integer of 0 to 2, preferably 1 or 2. When the heterocyclic ring is phenyl, furyl, pyrazolyl, imidazolyl, pyrimidinyl, pyrazinyl or pyridazinyl, the number of Z is an integer of 0 to 3, preferably an integer of 0 to 2, more preferably 1 or 2. It is. When the heterocyclic ring is pyranyl or pyridyl, the number of Z is an integer from 0 to 4, preferably an integer from 0 to 2, and more preferably 1 or 2.

The preferred range of T ⁷ is the following groups.

That, T ⁷ I: H, phenyl, benzyl or C, or a -C ₄ alkyl, there have to form a 5- or 6-membered ring together with the carbon atom bonded to the T ⁷ and T ^8. The preferred range of T ⁸ is the following groups.

That, T ⁸ I: forming phenyl, benzyl or C, -C ₄ alkyl or is, or a 5- or 6-membered ring together with the carbon atom to which the T ⁷ and T ⁸ are attached.

The preferred range of U ¹ is a group shown below.

That, U'I: H, Ci~C ₄ alkyl or C ₂ ~ (: ₅ or alkylcarbonyl, U 'and 5-membered ring together with the carbon atom to which U ² and is bonded, 6-membered ring, 7-membered It may form a ring.

Preferred ranges of U ² are the following groups.

That is, U ² I: H, C> to C ₄ alkyl or C _{2 to} C ₅ alkylcarbonyl, or a 5-membered ring, a 6-membered ring, and a 7-membered ring together with the carbon atom to which U ¹ and U ² are bonded. It may form a ring. Each group in the above-mentioned preferred substituent range can be arbitrarily combined, and the particularly preferred range of the compound of the present invention is shown below.

That is, the preferred range of the substituent is AI, BI, GI, RI, R 'I, nl, YI, WI, T'I, T 2 I, T 3 I, T 4 I, T 5 I, T 6 I, ^{XI, ZI, T 7 I,} T 8 I, the present compound Ru U'l and U der.

A preferred range of the substituent is AII, BI, GII, RI, RI, n K YI, WI, ΤΊ, T 2 I, T:, T 4 I, T 5 I, T 6 I, XI, ZI, T 7 I , T ⁸ I, the onset is ITI and U ² I Light compound.

Preferred substituent ranges are ΑΠ, BI, GIIK RI, n IKY YI, WI, T'K T ² I, T ^{: i} I, T ⁴ I, T ⁵ I, T ⁶ I, XI, ZI, T ⁷ I , T ⁸ I, the present invention of compounds which is U'l and U ² I.

A preferred range of the substituent is AIII, BI, GIIK RI, nll , YI, T'K T 2 I, T, T 4 I, T 5 I, T 6 I, XI, ZI, T 7 I, T 8 I, The compound of the present invention, which is ITI and U ² I. Preferred substituent ranges are ΑΙΠ, BII, GII, RIK RK nl, YII, TK

^{T 2 I, T 3 I,} T 4 I, T 5 I, T 6 I, xn, ζπ, τ 7 ι, T 8 I, a compound of the invention which is iri and u ² i.

A preferred range of the substituent is ΑΙΠ, BIIK GIIK RIIK R'lK nl, YIK T II, T 2 I, T 3 I, T 4 I, T 5 I, T 6 I, XIII, ZII, T 7 I, T 8 I, a compound of the invention which is U ^L I and U ² I.

A preferred range of the substituent is AIII, BIIK GIIK RIIK nll, YIK T'III, T 2 I, T 3 I, T 4 I, T 5 I, T 6 I, XIII, ZII, T 7 I, T 8 I, And U ² I.

A preferred range of the substituent is AIV, BIIK GIIK RIIK nll, YIK T ΊΙΚ T 2 I, T 3 I, T 4 I, T 5 I, T 6 I, XIII, ZII, T 7 I, T 8 I, U ' Compounds of the invention which are l and u.

A preferred range of the substituent is AIV, BIV, GIIK RIIK nll, YIK ΤΊΙΚ T 2 I, T 3 I, T 4 I, T 5 I, T 6 I, XIII, ZII, T 7 I, T 8 I, the ITI A compound of the present invention that is U ² I.

 Preferred substituent ranges are AV, BIIK GIIK RIIK n IK YIK T IKT

^{2 i, T 3 I, T} 4 I, T 5 I, T 6 I, XIII, ζπ, τ 7 ι, T 8 I, the onset bright compound is iri and u ² i.

A preferred range of the substituent is AV, B IV, GIIK RIIK ηΠ , YIK Τ'ΙΙΚ Τ 2 I, Τ 3 Ι, Τ 4 Ι, Τ 5 Ι, τ ", χιπ, ζπ, Τ 7 Ι, τ 8 ι, The compounds of the present invention which are ι'ι and υ ² ι.

A preferred range of the substituent is AVI, BIIK GIIK RIIK nll, YIK ΤΊΙΚ T 2 I, Τ 3 Ι, Τ 4 Ι, Τ 5 Ι, Τ ", XIII, ΖΙΙ, Τ 7 Ι, τ 8 ι, and υ'ι発² ι is the origin Light compound.

A preferred range of the substituent is AVI, BIV, GIIK RIIK nll, YII, ΤΊ1Κ T 2 I, T 3 I, T 4 I, T 5 I, T 6 I, XIII, ZII, T 7 I, T 8 I, U 'l and U are present compounds.

Then Q, A, B, G, R, R ', Y, W, X, Z, TT 2, T 3, an example of the atoms and groups in the definition of ^{Ύ T 5, TTT 8, U} 1 or IT Show.

 The halogen atom in the definition of G, RW, X, Y or Z includes a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, preferably a fluorine atom, a chlorine atom and a bromine atom.

B, R ', G, Τ ', Τ 2, Τ 3, Τ 4, Τ 5, Τ 6, Τ 7, Ύ UU 2, W, X, the alkyl in the definition of Υ or ζ represents a linear or branched Methyl, methyl, η-propyl, isopropyl, η-butyl, isobutyl, tert-butyl, sec-butyl, pentyl-1, pentyl-2, pentyl-3, 2-methylbutyl-1, 2-methylbutyl-2, 2- Methylbutyl-3,3-methylbutyl-1,2,2-dimethylpropyl-1, hexyl-1, hexyl-2, hexyl-3, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl , 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl Butyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl pill, 1-ethyl-2-methylpropyl, n-heptyl, n-octyl, n-nonyl, n-endenrile, n-dodenrile, n-tridene ^) re, n-tetradenrile, n-pentydecyl, n-hexadecyl, n-heppudecyl, n_ocdecyl, n-nonadecyl, n-icosyl And so on, and are selected within the range of each specified carbon number.

G, The alkenyl in the definition of TTT ^5, T ^fi or W, Chokukusarima other Eteniru as branched alkenyl, 1 one propenyl, 2-Purobe alkenyl, 1 Buteniru, 2-butenyl, 3-butenyl , 1-methyl_2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1_methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1_methyl-3-butenyl, 2_methyl-3-butenyl, 3-methyl-3-butenyl, 1, 1-dimethyl_2-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl , 5-hexenyl, 1-methyl-2 -pentenyl, 2 -methyl-2 -pentenyl, 3 -methyl-2 -pentenyl, 4 -methyl-2 -pentenyl, 1-methyl-3 -pentenyl, 2 -methyl-3 Pentenyl, 3-methyl_3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-1 4-pentenyl, 2-methyl-4 pentenyl, 3-methyl-4 1-pentenyl, 4-methyl-4-1-pentenyl, 1,, 1 —Dimethyl-2-butenyl, 1,1-dimethyl—3-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-2-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3- Butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-2-butenyl , 2-ethyl-2-butenyl, 1,1,2-trimethyl-2-probenyl, 1-ethyl-1-methyl-2-propenyl, etc., each of which is selected from the specified carbon number range. You.

 Alkynyl in the definition of G or W includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl as a linear or branched alkynyl , 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, hexynyl, 1-methyl-3-pentynyl, 1-methyl-4 Pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-Dimethyl-3-butynyl, 2,2-Dimethyl-3-butynyl, 1-ethyl 2-butynyl, 1-ethyl-3 Ethynyl, 2-Echiru 3-butynyl and the like, is selected from the range of the specified number of carbon.

Haloalkyl in the definition of B, G, ΎW, X, Y or Z is straight chain Or as branched haloalkyl, fluoromethyl, chloromethyl, bromomethyl, fluoroethyl, chloroethyl, bromoethyl, fluoro-n-propyl, chloro-n_propyl, difluoromethyl, chlorodifluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, difluoroethyl, trifluoromethyl Chloroethyl, chlorodifluoromethyl, bromodifluoromethyl, trifluorochloroethyl, hexafluoro-n-propyl, chlorobutyl, fluorobutyl, chloro-n-pentyl, fluoro-n-pentyl, chloro-n— Hexyl, fluoro-n-hexyl, etc. are selected from each of the specified carbon number ranges.

W, in the definition of T Ύ Τ ⁵ or Τ ^6, C, ~ (: As good C ₃ -C ₆ cycloalkyl optionally substituted with ₃ alkyl, cyclopropyl, 1-Mechirushiku port propyl, 2, 2, 3,3, -tetramethylcyclopropyl, cyclobutyl, 1-ethylcyclobutyl, 1-n-butylcyclobutyl, cyclopentyl, 1_methylcyclopentyl, cyclohexyl, 1-methylcyclohexyl, 4-methylcyclohexyl, etc. Is raised.

B, in the definition of W, or T ^1, as the C! CA alkyl substituted with R ^a, benzyl, 2 _ black hole benzyl, 3-bromobenzyl, 4-black port benzyl, 4 one-methylbenzyl, 4 Isseki Tert-butylbenzyl, 1-phenylethyl, 1- (3-chlorophenyl) ethyl, 2-phenylethyl, 1-methyl-11-phenylethyl, 1-1 (4-chlorophenyl) 1-1-methylethyl, 1- (3— 1-Methylethyl, 1-phenylpropyl, 2-phenylpropyl, 3-phenylpropyl, 1-phenylbutyl, 2-phenylbutyl, 3-phenylbutyl, 4-phenylbutyl, 1-methyl-1-phenyl Enylpropyl, 1-methyl_2-phenylpropyl, 1-methyl-3-phenylpropyl, 2-methyl-2-phenylpropyl, 2- (4- Yl) - 2-methyl - propyl methylphenol, 2-methyl - 2- (3-methylphenyl) propyl, and the like.

In the definition of T ', as a C ₃ to CS cycloalkyl substituted with R ^a, 1-phenylpropyl, cyclopropyl, 1 i (3 black port phenyl) cyclopropyl, 1- (4 one black port phenyl) cyclo Propyl, 1- (4-bromophenyl) cyclopropyl Mouth pill, 1- (4-fluorophenyl) cyclopropyl, 1- (4-ethylphenyl) cyclopropyl, 1- (4-propylphenyl) cyclopropyl, 2-phenylcyclopropyl, 1-phenylcyclobutyl, 2-phenylcyclobutyl, 1-phenylcyclopentyl, 1_ (4-cyclophenyl) cyclopentyl, 2-phenylcyclopentyl,, 3_phenylcyclopentyl, 1-phenylcyclopentyl, 1- (3— Fluorophenyl) cyclohexyl, 1- (4-cyclophenyl) cyclohexyl, 1- (4-tert-butylphenyl) cyclohexyl, 2-phenylcyclohexyl, 3-phenylcyclohexyl, 4-phenyl Nilcyclohexyl and the like.

In the definition of T ¹ , cyclopropyl substituted with R ^a and C, to C ₄ alkyl includes 2,2-dimethyl_1-phenylcyclopropyl, 1- (4-chlorophenyl) —2,2 —Dimethylcyclopropyl, 2,2-dimethyl-3-phenylcyclopropyl, 3- (3-chlorophenyl) -1,2,2-dimethylcyclopropyl, (4-chlorophenyl) 1,2,2- Dimethyl-3-phenylcyclopropyl, (4-bromophenyl) -1,2,2-dimethyl-3-phenylphenylpropyl, 2,2-dimethyl-3- (4-methylphenyl) cyclopropyl, (4-dimethylphenyl) Arylbutylphenyl) 1,2,2-dimethyl-3-phenylcyclopropyl and the like.

In the definition of T ^1, as C ₃ -C ₄ a cycloalkyl substituted with R ^e and halogen atoms, 2, 2-dichloro-one 1 one phenylpropyl cyclopropyl, 2, 2-dichloroethylene Rollo one 1 i (3- Cyclopropyl) cyclopropyl, 2,2-dichloro-1- (4-methoxyphenyl) cyclopropyl, 2,2-dichloro-1- (4-ethoxyphenyl) cyclopropyl, 2,2-dichloro-1-1 (4-1) i-Propyloxyphenyl) cyclopropyl, 2,2-dichloro-1- (4-t-butylphenyl) cyclopropyl, 2,2-dichloro-11- (4-methoxyphenyl) -13-phenylcyclo Propyl, 1- (4-ethoxyphenyl) -2,2,3,3, -tetrafluorobutyl and the like.

In the definition of T ¹ , cyclopropyl substituted with R ^d and C, to C ₄ alkyl includes 2,2-dimethyl-3- (2,2-dimethylethenyl) cyclopropyl 3- (2,2-dibutene moethenyl) -1,2,2-dimethylcyclopropyl, 3- (2,2-dichloroethenyl) 1,2,2-dimethylcyclopropyl, 3- (2,2-chloro Trifluoroethenyl) —2,2-dimethylcyclopropyl and the like.

In the definition of T ¹ , C ₃ , to (( ₃ ) C _{3 to} C <cycloalkoxy which may be substituted by alkyl, include cyclopropoxy, cyclobutoxy, cyclopentoxy, cyclohexyloxy, 1-methylcyclopropy Kishi and the like.

In the definition of T ', as the alkenyl C ₂ -C ₄ substituted with R ^a, 1-safe Enirueteniru, 2 _ phenylene Rueteniru, 2- (2-black port phenyl) Eteniru, 2 - (3-Black Methyl phenyl, 2- (4-chlorophenyl) ethenyl, 2- (4_methylphenyl) ethenyl, 2- (2,6-difluorophenyl) ethenyl, 2- (2,5-dimethylphenyl) ethenyl , 1-Methyl-2-phenyl-2-ethenyl, 2-phenyl_1-propenyl, 2- (4-bromophenyl) -1-1propenyl, 2- (2,4,6-trimethylphenyl) 1-1-pro Phenyl and the like.

In the definition of G, Τ ', T ² , T ³ , W, X, ア ル コ キ シ or Ζ, straight-chain or branched-chain alkoxy is methoxy, ethoxy, η-propoxy, isopropoxy, η-butoxy, isobutoxy , Sec-butoxy, tert-butoxy, n-pentyloxy, 1-methylbutyloxy, 2-methylbutyloxy, 3-methylbutyloxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2 , 2-dimethylpropoxy, 1-ethylpropyloxy, n-hexyloxy, 1-methylpentyloxy, 2-methylpentyloxy, 3-methylpentyloxy, 4-methylpentyloxy, 1, 1-dimethylbutyloxy, 1,2-dimethylbutyloxy, 1,3-dimethylbutyloxy, 2,2-dimethylbutyloxy, 2,3-dimethylbutyl Oxy, 3,3-dimethylbutyroxy, 1-ethylbutyloxy, 2-ethylbutyloxy, 1,1,2-trimethylpropyloxy, 1,2,2-trimethylpropyloxy, 1-ethyl 1-methylpropyloxy, 1-ethylpropyl-2-methylpropyloxy, n-heptyloxy, n-octyloxy, n-nonyloxy, n_decyloxy Are selected from each of the specified carbon number ranges.

Examples of the halocycloalkyl of c _{3 to} c ₆ in the definition of W or T ¹ include fluorocyclopropyl, difluorocyclopropyl, chlorocyclopropyl, dichlorocyclopropyl, 1-methyl-2,2-dichlorocyclopropyl, and chlorocyclobutyl. And dichlorocyclobutyl, chlorocyclopentyl, dichlorocyclopentyl, chlorocyclohexyl, dichlorocyclohexyl, tetrafluorocyclobutyl and the like.

G, RT \ W, X, Y or methyl Amino As an NU 'U ² in the definition of Z, Echiruamino, n- Puropiruamino, isopropyl § amino, n - butyl Amino, Isobuchiruamino, sec - Puchiruamino, tert - Puchiruamino , N-pentylamino, 1-methylbutylamino, 2-methylbutylamino, 3-methylbutylamino, 1,1-dimethylpropylamino, 1,2-dimethylpropylamino, 2,2-dimethylpropylamino Mino, 1-ethylpropylamino, n-hexylamino, 1-methylpentylamino, 2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino, 1,1-dimethylbutylamino, 1 , 2-Dimethylbutylamino, 1,3-Dimethylbutylamino, 2,2-Dimethylbutylamino, 2,3-Dimeterbutylamino No, 3,3-dimethylbutylamino, 1-ethylbutylamino, 2-ethylbutylamino, 1,1,2-trimethylpropylamino, 1,2,2-trimethylpropylamino, 1-ethyl — 1-Methylpropylamino, 1-Ethyl — 2-Methylpropylamino, Dimethylamino, Getylamino, Di-n-propylamino, Diisopropylamino, G-n-Ptylamino, Di-sec—Butylamino, Disoptylamino N-pentylamino, di-n-hexylamino, methylethylamino, methylpropylamino, methylisopropylamino, methylbutylamino, methyl-sec-butylamino, methylisobutylamino, methyl-tert-butylamino , Methylpentylamino, methylhexylamino, ethylpropylamino E chill isopropylamino, E chill Petit Rua Mino, Echiru sec - butylamine Bruno, E chill iso Petit Rua Mino, E chill pliers Rua Mino, Kishiruamino to Echiru, Fueniruamino, Benjiruamino, N- Mechiruasetoami de, N- Echiruaseto Amide, N-phenylacetamide, N-acetylacetamide, etc. are selected, and each is selected within the specified carbon number range.

 The alkoxycarbonyl in the definition of G, RTW, X, Y and Z includes methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, iso-propoxycarbonyl, n-butoxycarbonyl, sec-butoxycarbonyl, iso-butoxycarbonyl, tert —Butoxycarbonyl, n-pentyloxycarbonyl, n_hexyloxycarbonyl, etc. are selected, and each is selected within the specified carbon number range.

G, TW, X, as the C i~C ₄ haloalkoxy in the definition of Y and Z, respectively C, and linear or branched haloalkoxy -C ₄ mentioned, Furuorome butoxy, difluoromethyl O b methoxy , Trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, dichlorofluoromethoxy, chloromethoxy, dichloromethoxy, trichloromethoxy, bromomethoxy, fluoroethoxy, chloroethoxy, bromoethoxy, difluoroethoxy , Trifluoroethoxy, tetrafluoroethoxy, penduorofluoroethoxy, trichloroethoxy, trifluorochloroethoxy, fluoropropoxy, chloropropoxy, bromopropoxy, fluorobutoxy, chlorobutoxy, fluoro iso-propoxy and chloro mouth is 0- propoxy, and the like.

In the definitions of G, T ² , TW, X, Y and Z, C, ~ (: 4 alkylsulfenyls include methylthio, ethylthio, η-propylthio, iso-propylthio, n-butylthio, iso-butylthio, sec-butylthio and tert-butylthio.

G, X, W, C put in the definition of Y and Z, as -C ₄ alkylsulfinyl is methylsulfinyl, E chill sulfinyl, n - propyl sulfinyl, iso one propyl sulfinyl, n- butylsulfinyl, iso- Buchirusurufi two Le , Sec-butylsulfinyl and tert-butylsulfinyl.

B, G, W, X, C in the definition of Y and Z, as -C ₄ alkylsulfonyl, methylsulfonyl, Echirusuruhoniru, n - propyl sulfonyl, iso _ propylsulfonyl, n - butylsulfonyl, IS 0- butyl Sulfonyl, se c-butylsulfonyl and tert-butylsulfonyl.

W, as the alkoxyalkyl C ₂ -C ₄ in the definition of T ¹ or Y, C _{~C:! I} alkoxy - methyl, C, -C ₂ alkoxy - Echiru, such Metokishetokishi methyl and methoxy propyl can give.

G, the alkyl carbonyl C ₂ -C ₄ in the definition of UU ² or W, Asechiru, propionyl, Butanoiru, iso _ Butanoiru the like.

Examples of the C ₂ -C _fi haloalkylcarbonyl in the definition of G include chloroacetyl, trifluoroacetyl, 3,3,3_trifluoropropionyl, pentafluoropropionyl and the like.

The W haloalkylcarbonyl O alkoxy of C2～C ₅ in the definition of black hole Asechiruokishi, triflumizole Ruo b acetyl O alkoxy, 3,3,3-triflate Ruo Ropuro Pio two Ruokishi, pen evening full O Ropuro -L Ruo alkoxy etc. can give.

C ₃ ~ in the Y definition (: The ₇ dialkylaminocarbonyl O knight, di methyl § iminocarbonyl O carboxymethyl, Jefferies chill § iminocarbonyl O carboxymethyl, di- i- propyl aminocarbonyl O carboxy and the like.

A, 1 one-naphthyl and 2-naphthyl as naphthyl in the definition of W and T ^1.

 Pyridyl optionally substituted with X in the definition of W includes 2-pyridyl optionally substituted with X, 3-pyridyl optionally substituted with X or XT 4-pyridyl optionally substituted with X And is preferably 2-pyridyl optionally substituted by X or 3-pyridyl optionally substituted by X, and more preferably 2-pyridyl optionally substituted by X.

 Chenyl which may be substituted by X in the definition of W includes 2-phenyl which may be substituted by X and 3-phenyl which may be substituted by X.

In the definition of W, R ¹ and Y — N = CT ⁷ T ⁸ means alkylideneamino, benzylideneamino, arylideneamino or cycloalkylideneamino, methylideneamino, ethylideneamino, propylidamino, isopropylidene Amino, 4-methyl-2-pentylideneamino, cyclopentylideneamino, cyclo Xylideneamino and the like.

The mono-alkylaminosulfonyl of C] -C ₄ in the definition of B, methylaminosulfonyl, E chill aminosulfonyl, n- propyl aminosulfonyl, isopropyl aminosulfonyl and n- butyl aminosulfonyl is Ru mentioned.

C ₂ ~ in the definition of B (: ₈ The dialkylaminosulfonyl, Jimechirua Minosuruhoniru, Jefferies chill aminosulfonyl, di n- propylamino sulfonyl le, etc. Jie isopropyl aminosulfonyl and di n- butyl aminosulfonyl and the like .

C ₂ -C ₅ monoalkylaminothiocarbonyl in the definition of B includes methylaminothiocarbonyl, ethylaminothiocarbonyl, n-propylaminothiocarbonyl, isopropylaminothiocarbonyl, n-butylaminothiocarbonyl and the like. Is raised.

C ₃ to (: ₉ dialkylaminothiocarbonyl in the definition of B include dimethylaminothiocarbonyl, dimethylaminothiocarbonyl, di-n-propylaminothiocarbonyl, diisopropylaminothiocarbonyl and di-n-butylaminothiocarbonyl. And thiocarbonyl.

In the definition of B, C ₄ , -C ₄ alkyl substituted by R ^b includes phenacyl, 2-fluorophenacyl, 3 _ clofenacyl, 4-bromophenacyl, 2-methylphenacyl, 3-methylphenacyl, 4-i- Propylphenacyl, 4-t-butylphenacyl and the like.

In the definition of B, halogen atom and C, as good phenylalanine alkylsulfonyl optionally substituted on 1 or more kinds selected from -C ₄ alkyl, 2-fluorophenyl sulfonyl, 4 one fluorophenylsulfonyl, 2- black port Phenylsulfonyl, 4-chlorophenylsulfonyl, 4-bromophenylsulfonyl, 2,5-dichlorophenylsulfonyl, penfluorophenylsulfonyl, 4-methylphenylsulfonyl, 2-methylphenylsulfonyl, 4-methylphenylsulfonyl t-butylphenylsulfonyl, 2,5-dimethylphenylsulfonyl, 2,4-dimethylphenylsulfonyl, 2,4,6-trimethylphenylsulfonyl, 2,4,6-tri-i-pro Pyrenylsulfonyl and the like.

The C ₂ -C ₅ cyanoalkyl in the definition of B includes cyanomethyl, 2-cyanoethyl, 3-cyanopropyl, 1-cyano 1-methylethyl, and the like.

C ₃ -C ₉ alkoxycarbonylalkyl in the definition of B includes methoxycarbonylmethyl, ethoxycarbonylmethyl, n_propoxycarbonylmethyl, i-propoxyl-proponylmethyl, n-butoxy as linear or branched alkoxycarbonylalkyl. Carbonylmethyl, i-butoxycarbonylmethyl, t-butoxycarbonylmethyl, n-hexyloxycarbonylmethyl, n-heptyloxycarbonylmethyl, 1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-n-butoxyshetyl, 2-methoxycarbonylethyl, 2-ethoxycarbonylethyl, 1-methoxycarbonylpropyl, 3-ethoxycarbonylpropyl, 4-methoxycarbonylbutyl, 6-ethoxycarbonylhexyl, 1-methoxy Aryloxycarbonyl - 1 - Mechiruechiru, 1 one iso- Provo Kishikarubo two Lou 1- Mechiruechiru, 1 one-ethoxycarbonyl - 2-Mechirupuro pills, and the like.

 Alkali metals in the definition of B include lithium, sodium, and potassium.

 Alkaline earth metals in the definition of B include magnesium, calcium, strontium or barium, preferably magnesium, calcium or barium.

The Anmoniumu represented by NHT ⁴ T ⁵ T ^fi in the definition of B, ammonium two © beam, monomethyl ammonium Niu arm, dimethyl ammonium Niu arm, trimethyl ammonium Niu arm, Jefferies chill ammonium Niu arm, tri E chill ammonium Niu arm, diisopropyl Ammonia, diisopropylethylammonium, hexylmethylammonium, cyclopropylmethylammonium, cyclohexylmethylammonium, arylmethylammonium, benzylmethylammonium or 4-methylcyclohexylammonium A 5-membered heterocyclic group which is a pentagon or which may contain an oxygen, nitrogen or sulfur atom together with the nitrogen atom to which each of T ⁴ , Τ ⁵ and Τ ⁶ is attached Ring, 6-membered, 7-membered or 8-membered ammonium etc. It is.

Two of τ ⁴ , τ ^5, and τ ⁶ in the definition of τ τ ⁵ or τ ⁶ may be a heterocyclic 5-member which may contain an oxygen atom, a nitrogen atom, or a sulfur atom together with the nitrogen atom to which each is bound. Examples of the ring, 6-membered, 7-membered or 8-membered ammonium include pyrrolidine, virazolidine, imidazolidine, oxazolidine, isoxazolidine, thiazolidine, piperidine, piperazine, morpholine, thiamine, and hexane. Examples include methyleneimine and heptamethyleneimine.

 As the haloalkylsulfenyl in the definition of G, W, X, Y or Z, as a straight-chain or branched-chain haloalkylthio, fluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio, trifluorofluoro Methylthio, trichloromethylthio, 2,2,2-trifluoroethylthio, 1,1,2,2-tetrafluoroethylthio, fluoroethylthio, Pennofluorethylthio and fluoro-iso-propylthio And so on.

 Haloalkylsulfinyl in the definition of G, W, X, Y or Z includes straight-chain or branched-chain haloalkylsulfinyl

Ynyl, chlorodifluoromethylsulfinyl,

Inyl, trifluoromethylsulfinyl, trichloromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 1,1,2,2-tetrafluoroethylsulfinyl, fluoroethylsulfinyl, pennofluoresulfinyl And fluoro-is 0-propylsulfinyl.

 As the haloalkylsulfonyl in the definition of G, W, X, Y or Z, as a linear or branched haloalkylsulfonyl, fluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, trifluoro O-methylsulfonyl, trichloromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 1,1,2,2-tetrafluoroethylsulfonyl, fluoroethylsulfonyl, pentafluoroethylsulfonyl and fluoro- is 0-propylsulfonyl and the like.

The haloalkenyl in the definition of G or W, C ₂ ~ (: as haloalkenyl ₄ linear or branched岐状2- Kuroroeteniru, 2 Buromoeteniru, 2, 2 Dichloroethenyl and the like.

G, The Arukeniruokishi in the definition of Ding ^1, W or Y, Ariruokishi as Arukeniruokishi straight or branched岐状, 2 Purobe Niruokishi, 2-butene Niruokishi, 2-methyl-2-propenyl Niruokishi And the like.

 As the haloalkenyloxy in the definition of G, W or Y, a straight-chain or branched haloalkenyloxy is 3-chloro-2-propenyloxy, 3,3-dichloro-2-propenyloxy, 4-chloro Mouth—2-butenyloxy, 4,4-dichro mouth—3-butenyloxy, 4,4-difluoro-3-butenyloxy and the like.

 Alkenylsulfenyl in the definition of G, W, X, Y or Z includes, as straight-chain or branched alkenylsulfenyl, arylsulfenyl, 2-propenylsulfenyl, and 2-alkenylsulfenyl. Butenylsphenyl, 2-methyl-2-proenylsulfenyl and the like.

 Alkenylsulfinyl in the definition of G, W, X, Y or Z includes, as straight-chain or branched alkenylsulfinyl, arylsulfinyl, 2-propenylsulfinyl, 2-butenylsulfinyl, 2-methyl- 2-provenylsulfinyl and the like.

 Alkenylsulfonyl in the definition of G, W, X, Y or Z includes, as straight-chain or branched alkenylsulfonyl, arylsulfonyl, 2-propenylsulfonyl, 2-butenylsulfonyl, 2-methyl-2-probedyl. Nylsulfonyl and the like.

 As haloalkenylsulfenyl in the definition of G, W or Y, straight-chain or branched-chain haloalkenylsulfenyl is 3-chloro-2-propenylsulfenyl, 4-chloro-2-phenyl Examples include phenylsulfenyl, 3,3-dichloro-2-probenylsulfenyl, 4,4-dichloro-3-butenylsulfenyl, and 4,4-difluoro-3-butenylsulfenyl.

As the haloalkenylsulfinyl in the definition of G, W or Y, straight-chain or branched-chain haloalkenylsulfinyl is 3-cyclo-2-propylenylsulfinyl, 3,3-diclocyclo-2-propylenyl Sulfinyl, 4-black mouth—2 —Butenylsulfinyl, 4,4-dichloro-3-butenylsulfinyl, 4,4-difluoro-3-butenylsulfinyl and the like.

 As the haloalkenylsulfonyl in the definition of G, W or Y, straight-chain or branched haloalkenylsulfonyl is 3-cyclo-2-propylenylsulfonyl, 3,3-dichloro-2-proenylsulfonyl, 4 Monoclonal—2-butenylsulfonyl, 4,4-dichloro mouth—3-butenylsulfonyl, 4,4-difluoro-3-butenylsulfonyl and the like.

 Haloalkynyl in the definition of G or W includes chloroethynyl, bromoethynyl, iodoethynyl, 3-chloro-1_propynyl, 3-bromo-1-butynyl and the like.

 The alkynyloxy in the definition of G, W or Y includes 2-propynyloxy, 2-butynyloxy, 1-methyl-2-propynyloxy and the like.

 Examples of haloalkynyloxy in the definition of G, W or Y include 3-chloro-2-propynyloxy, 3-bromo-2-propynyloxy, 3-iodo-2-propynyloxy and the like.

 The alkynylsulfenyl in the definition of G, W or Y includes 2-propynylsulfenyl, 2-butynylsulfenyl, 1-methyl-2-propynylsulfenyl and the like.

 Alkynylsulfinyl in the definition of G, W or Y includes 2-propynylsulfinyl, 2-butynylsulfinyl, 1-methyl-2-propynylsulfenyl and the like.

 Alkynylsulfonyl in the definition of G, W or Y includes 2-propynylsulfonyl, 2-butynylsulfonyl, 1.1-methyl-2-propynylsulfonyl and the like.

 Haloalkynylsulfenyl in the definition of G, W or Y includes 3-chloro-2-propynylsulfenyl, 3-bromo-2-propynylsulfenyl, and 3-propynylsulfenyl. And the like.

Haloalkynylsulfinyl in the definition of G, W or Y includes 3-chloro-12-propynylsulfinyl, 3-bromo-2-propynylsulfinyl, 3-odo-2 -propynylsulfinyl and the like.

 Examples of haloalkynylsulfonyl in the definition of G, W or Y include 3-chloro-2-propynylsulfonyl, 3-bromo-2-propynylsulfonyl, 3-thio-2-propynylsulfonyl and the like.

 Examples of the alkylcarbonyloxy in the definition of G, W or Y include acetoxy, propanoyloxy, bushyloxy, isopropylcarbonyloxy and the like, and each is selected within the range of the specified number of carbon atoms.

 Benzoyl which may be substituted by X in the definition of G includes benzoyl, 2-chlorobenzoyl, 3-chlorobenzoyl, 4-chlorobenzoyl, 4-bromobenzoyl, and 4-fluorobenzoyl. , 3-Methylbenzoyl, 4-Methylbenzoyl, 4-Yuichisharybutylbenzoyl, 3,4-Dichlorobenzoyl and the like.

 The compound of the present invention is stored in so-called agricultural pests that infect agricultural and horticultural crops and trees, so-called livestock pests that infest livestock and poultry, so-called sanitary pests that have various adverse effects on human living environments such as houses, and stored in warehouses. It can effectively control so-called stored pests that injure crops and other insects, as well as mites, nematodes, molluscs, and crustaceans that occur and injure in similar situations at low concentrations.

Specific examples of insects, mites, nematodes, molluscs, and crustaceans that can be controlled using the compound of the present invention include the following, but are not limited thereto. Nikameiga, Kobunomeiga, Futaobikoyaga, Ichimonjiseseri, Konaga, Kotoga, Monshirocho, Rikiburaga, Hasunoto, Shiroichimonjoto, Otobacuga, Chinokomokumamaki, Chiyahamaki, Momoshinki-mon, Momoshin-ki-mokin, Momo-shin-ko-moki, Momo-sinki-mon, Momo-shin-ko-moki, Momo-sinki-mon Worms, tobacco bad worms, balsam bean corn borers, fall army worms, codling moths, and american white-headed pests such as Lepidopteran pests, Leafhoppers, Tobi-Irojin-power, Momoka-aphids, Aphid aphids, Onshiko-nashi lice, and Sir-bar-leaf lice , Pear lice, ledge danbai, anopheles mosquitoes, lycopodium mosquitoes, ruby beetles, oowal oysters, ku Gikame worms, Hemiptera such as longer and bedbugs, two free catcher vigintioctopunctata, de ゥ ネ, 、 、 マ イ シ イ イAnd Coleoptera pests such as P. japonicus, P. terrestrial flies, Pseudomonads, Hesian flies, Perfume flies, Drosophila melanogaster, Musca domestica, Rhinoceros flies, Higgsila flies, Kisujishoe flies, Pseudophyta, Pseudophyceae, Pseudophyllophyllis, flies, Dipterous pests such as Anetai Shima, Aedes albopictus and Sinama anura Hymenoptera pests such as Lahabium, Matsunobachi, Kurihabachi, Dantai ant, Cryoanthus, Papilio hornet, Bulldog ant, Fireant ant and Pharaoh ant Orthopterous pests such as ゥ 網, Reticulosa pests such as black cockroaches, yamato cockroaches, and brown cockroaches, Orthopterous pests such as oaks, emma crickets, tosamababa, kobanenago and mackerel ribatta, house termites, yamato termites And termite pests such as Ivan termites, isopteran pests such as cat fleas, human fleas and capsid fleas, and white lice pests such as white lice and white lice, white lice, black lice,シ ラ Louse pests such as white lice and porphyrus lice; gross pests such as black lice; Two kinds of mites, two kinds of mites, two kinds of mites, two kinds of mites, such as tulip rust mites and tyrannifers, two kinds of mites, such as red mite and cyclamen mite; Two kinds of ticks, such as the ticks mite, the red mite, such as Hiduki mite, the mite, such as Hizen mite, and the lip legs, such as Tobism kade, Akasum kade, and Ogejigeji , Yakeyasude, Diplopoda such as Fujiyasude, whip My Monet Cobb centimeter Yu, key evening Nekobusenchiyuu, key evening Negu Saleh centimeter Yu, walnut Negu Saleh centimeter Yu, potato cyst centimeters Nematodes such as yu and pine wood smelt, mollusks such as porcupine snails, slugs, alfalfa maimai, mussels and mussels and crustaceans such as locust beetles.

 The plant diseases to be controlled by the compound of the present invention include rice blast (P yriculariaoryzae), sesame leaf blight (C ochliobo 1 usmiyabeanus), sheath blight (Rh izoctoniasolani), and wheat powdery mildew (E sp.hortici, f.sp.tritici), Leaf spot (Py renophoragraminea), Nettle spot (Py renophorateres), Leaf blight (Gibberellazeae), Rust (Pucciniastriiformis, P. gr am inis, P. recondita, P. hordei), Snow rot (T yphu 1 as., Micronectriel 1 anivais), Naked smut (U sti 1 agotritici, U. nuda), Eye spot (P seudocercospore 1 1 aherpotrichoides) , Dwarf disease (Rhyn chospori um secalis), Leaf blight (Septoriatritici), Fusarium wilt (L eptosph) a e r i a n o d o r um), sunspots of rickets, disease (Dia p o r t h e c i t r i), scab (E ls i n o e f a wc e t t i) Fruit rot

(Penicilli um digitat um, P. italic um), U coral monilia disease (S clerotinia ma li), rot (Va1 sama 1 i), powdery mildew (Podosphaeraleucotricha), spotted leaf spot (Alternaria) ma li), scab (Venturiainaequalis), pear scab (Venturianashicola), black spot (A 1 ternaria K ikuchiana), red scab

(Gymn osporangi um haraea num), peach rot disease (S 'c 1 erotiniacinerea), Kuroboshi (CI adospori um carpophil um), phomopsis rot (Phomo psiss p.), Grape downy mildew (P la smo paraviticola), black rot (E lsinoe amp e 1 ina), scab (G 1 omere 1 1 ac) ingu 1 ata), powdery mildew (Unci nu lanecator), rust (Phakopsoraampelopsidis), anthracnose of ikiki (G 1 oeospori um kaki), deciduous disease (Cercosporakaki, My cosphaere 1 1 an awa e) , Downy mildew (P seudoperenosporac υ bensis), Poison (Co 1 1 etotrich um 1 agenari um), Powdery mildew (S phaerothecafu 1 iginea), Vine blight (My cosphaere 1 la me lonis) , Tomato plague (Phy tophthorainfestans), ring spot (A 1 ternariasolani), leaf mold (C ladosporiumfu 1 vam), eggplant brown spot (Phomo psisvexans), powdery mildew (Erysiphecichoracoar um), Black spot (A 1 ternariajaponica), white spot (C erocospore 11 arassicae), rust of Paki (P ucciniaa 11 1 ii), soybean purpura (C ercosporakikuchii) E lsinoeglycines), Black spot disease (D iaporthe

P haseo 1 o 1 um), Anthracnose of Cingen (Colletotrichum 1 ind emu thian um), Black astringency of Lackasey; ιhei (My cosphaere 1 lapersonat um), te spot (Cercosporaarachidicola), Endo noodles Disease (E rysiphepisi), potato summer blight (Alternariasolani), strawberry powdery mildew (S phaerothecah umu 1 i), stalk net blast (E obasidi um reticu 1 at um), Shirasato bye (E lsinoeleucospila) , Scab of the evening saw (A 1 ternaria. I ongies), Erysihecichoracear um, scab (Col 1 etotrich um tabac um), brown spot of sugar beet (Cercosporabetico 1 a) , Black scab (Dip 1 ocarponrosae, Sphaerothecapannosa), Brown spot of chrysanthemum (S eptoriachrysanth em iindic), White rust (Pucciniahoriana), Gray of various crops Botrytiscinerea Bacterial sclerotia of various crops (Sc1erotiniasclerotior um) and the like.

 That is, the compound of the present invention can effectively control pests and plant diseases of Orthoptera, Hemiptera, Lepidoptera, Coleoptera, Hymenoptera, Diptera, Termites and Acari and Lice at low concentrations, while The compounds of the present invention include extremely useful compounds that have little adverse effect on mammals, fish, crustaceans and beneficial insects.

The compound of the present invention can be synthesized by the following method (Scheme 1).

Scheme 1

(Method A)

 -L (4) A

Q-CH ₂ CN + or

(3) (AC0) ₂ 0 (5) Q OH

 (ΐ ')

B_L "(8), DHP,

 Isocyanate Q Ο -Β

 Or 7-year-olds (1)

 (Method B)

Q (ΐ ')

(Method C) .CN

 H (1 ')

* C0 ₂ -alkyl

 (9) (10)

[Wherein Q, A and B in (Scheme 1) have the same meanings as described above, and L is a good leaving group such as a chlorine atom, a bromine atom, C! C alkoxy, phenoxy, 1-pyrazolyl or 1-imidazolyl. L ′ represents a halogen atom, a good leaving group such as (^ to ア ル alkylsulfonyloxy, benzenesulfonyloxy, toluenesulfonyloxy), L ″ represents a halogen atom, and alkyl represents Alkyl, preferably C 1, to C ₄ alkyl.

Method (A) in (Scheme 1) comprises an acetonitrile derivative represented by the general formula (3) and an acid chloride or ester represented by the general formula (4), or an acid represented by the general formula (5). A method for synthesizing the compound of the present invention (1 ′) by reacting with an anhydride will be described. Further, the compound of the present invention (1 ′) is an alkyl halide represented by the general formula (8), an alkyl sulfonate, a trimethylsilyl halide, a sulfonyl chloride, a sulfamoyl chloride, a thiocarbamoyl chloride, The compound (1) of the present invention can be converted by reacting with an acid chloride or an ester. At this time, depending on the type of B in the compound (1) of the present invention, dihydropyran, isocyanates or thioisocyanate may be added to the compound (1 ′) of the present invention. And are synthesized by reacting them. By using (4) or (5) in excess in Method A, (1) can also be directly synthesized without isolating (1 ′).

 When Q is bonded to the acrylonitrile moiety by a nitrogen atom, it can also be synthesized by Method B. Method B refers to a method of synthesizing the compound of the present invention (1 ′) by reacting the heterocyclic ring represented by the general formula (6) with the hapenocyano ketone derivative represented by the general formula (7).

 When A is bonded to the acrylonitrile moiety with a nitrogen atom, it can also be synthesized by Method C. Method C refers to a method of synthesizing the compound of the present invention from a cyanoacetic acid derivative represented by the general formula (9) and a heterocyclic compound represented by the general formula (10). In some cases, the compound represented by the general formula (9) can be synthesized by reacting an acetonitrile derivative represented by the general formula (3) represented by the method A with a carbonate in the presence of a base.

 In some cases, it is preferable to use a base in the methods described in (Scheme 1) and (Scheme 2). Examples of the base used include alkali metal alkoxides such as sodium ethoxide, sodium methoxide, potassium t-butoxide, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, sodium carbonate, and lithium carbonate. Organic bases such as alkali metal carbonates, triethylamine, pyridine, and DBU; organic lithium compounds such as butyl lithium; lithium diisopropylamine; lithium amides such as lithium bistrimethylsilyl amide; and sodium hydride. Can be

The reaction shown in (Scheme 1) can be performed in a solvent inert to the reaction, and the solvent may be lower alcohols such as methanol and ethanol, aromatic hydrocarbons such as benzene and toluene, getyl ether, and the like. Ethers such as tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane, 1,2-dietoxetane, halogenated hydrocarbons such as methylene chloride, chloroform, 1,2-dichloroethane, and dimethyl Examples include amides such as formamide and dimethylacetamide, acetonitrile, dimethylsulfoxide and a mixed solvent thereof. In some cases, a mixed solvent of these solvents and water can also be used, and it is preferable to add a quaternary ammonium salt such as tetra-n-butylammonium amide as a catalyst. In some cases, results may be obtained. The reaction temperature can be set at any temperature from -30 to 200 ° C, and preferably from 0 ° C to 15 Ot: or from 0 to the boiling point of the solvent when a solvent is used. The base is used in an amount of 0.05 to 10 equivalents, preferably 0.05 to 3 equivalents, of the reaction substrate.

 The compound of the present invention can be obtained from the reaction solution by a conventional method, but if it becomes necessary to purify the compound of the present invention, it can be separated and purified by any purification method such as recrystallization or column chromatography. .

 In the compounds included in the present invention, compounds having an asymmetric carbon include optically active compounds (+) and (1).

 Compound (3) in (Scheme 1) can be synthesized according to the method described in International Patent Application Publication (WO 97Z40009).

 Examples of the compounds included in the present invention are shown in Tables 1 to 4. The abbreviations in the table have the following meanings, respectively.

Me: methyl, Et: ethyl, Pr: propyl, Bu: butyl, Pen: pentyl. Hex: hexyl, Hep: heptyl, Oct: octyl, Non: nonyl, Dec: Decyl, Ph : Phenyl, n: Normal, i: Iso, sec: Secondary, t: Yuichi Shary, c: Cyclo,

R 1: R R R 4

O '

 R 5 R 6: R

 G Gu N

⁰

o

R 9: R 1 0: R 1 1 R 1 2

^s

 R 13: R 1 R 15: R 16

 G S N

G G

 S 'N ヽ

R R 20:

R 2 5: R 2 6

 N G ",

S '

Ad / 0dTL 3900

e

I

 O

B 4: CF ₃ S0 ₂ — B 5: CH ₃ S0 ₂ — B 6

 Ph

O O

B B 8 B 9 Et, NH

 MeO

B 1 0:

Ph O: B1 4

B 1 3 Me ₃ Si-: NS0 ₂ — B 15:

 H 'Me

O

B 16: II B 17 ° B 18: ° F ₃ C cue ¾uNH

O

 B 1 9

B 2

4: CH ₃₀ (CH ₂ ) ₂ OCH ₂ —

B26: PhSO—

B 3 2: CH ₃ SCH ₂ — B 3 3: CH ₃ CH ₂ OCH ₂

Z £ 90 / 00dT / 13d (Table 1)

Rl H 5-Me H H H Me

R2 H 5-C1 Bl Me H Et

R3 H 1-Me B2 Me Me nPr

R3 H U Me B8 Me Me Me

R3 H 1-Me B8 Me CI Me

R3 H 1-Me B8 CI CI Me

R3 H 1-Me B8 CF ₃ CI Me

R4 H 4-Me B3 Me CI iPr

R5 H 2-Me-5-CF ₃ B4 CI CI nBu R6 H 4-Ph B5 CI H iBu

R6 HH B8 Me Me Me

R7 H 5-Me B7 CF ₃ CI Me

R7 H 5-Me B7 Me CI Me

R7 H 5-Me B7 CI CI Me

R8 H 3-MeO-5-NH ₂ B7 CF ₃ H 'tBu

R9 HH B8 CF ₃ CI Me

RIO H 2-MeS-4-NH ₂ B9 CF ₃ CI Me

Rll HH BIO CI CF ₃ Me

 R12 Me H B7 CI CI Me

R13 H 4-Br B12 CI Me Me

R14 H 3-nPrO B13 MeO CI Me

R15 H H B14 EtO MeS Me

R16 H H B15 CN CI Me

R17 H l-Me-3, 5-C B16 CN NH2 Me

R18 H 1, 5-Me ₂ B17 NO 2 CI Me

R19 H 1, 3-Me ₂ B18 NO 2 MeO Me

R20 H U Me B19 H H Me

R21 H U Me B20 Me H Me

R22 H 5-Ph B21 Me Me Me

R23 H 3-Me B22 Me CI Me

R24 H 5-MeO B24 CI CI Me

R25 H 5-Ph B25 CI H Me

R26 H 3-Ph B26 CF ₃ H Me

R28 H 4-Me-2-Ph B28 CF ₃ CI Me

R29 HH B29 CF ₃ CI Me

R31 H l-Me-4-NH ₂ B31 CI CF ₃ Me

R32 H H B32 CI Me Me

R33 H H B33 MeO CI Me

R33 H H H Me Me Me

R33 H H H Me CI Me

R33 H H H CI CI Me

R33 HHH CF _{; i} CI Me

R33 H H B6 Me Me Me

R33 H H B6 Me CI Me

R33 H H B6 CI CI Me

R33 HH B6 CF ₃ CI Me

R33 H H B7 Me Me Me

R33 H H B7 Me CI Me

R33 H H B7 CI CI Me

R33 HH B7 CF _{: i} CI Me

R33 H H B8 Me Me Me

R33 H H B8 Me CI Me

R33 H H B8 CI CI Me

R33 HH B8 CF ₃ CI Me

R33 H H B9 CI CI Me

R33 H H B15 Me Me Me

R33 H H B15 Me CI Me

R33 H H B15 CI CI Me

R33 HH B15 CF ₃ CI Me

R33 H H B16 Me Me Me

R33 H H B16 Me CI Me

R33 H H B16 CI CI Me

R33 HH B16 CF ₃ CI Me 1-9

 aw 3W 3N 519 H sen

13 ^; d3 sia H

 13 13 S19 H

 13 3W 8a H

 aw 3N 89 H

 13: i 89 C-H

 13 13 88 S3W- H

 13 3W, a H

ID ⁵ d3 9N- H

 ID 13 za 13-H

 aw 13 3 ia H

 3W 3W 98 H

13 ^E J3 99 09W-1 H

 ID 13 99 9W-1 H

 13 aw H H

 9 H 3- ^ H

 13 H S3W-H

 9W Ϊ3 13 H 09W- 1 H

 ID 9W H H

 aw 13 H H

 13 13 ea H H

 9N 13 9W tea H H

 9W aw 3W sa H

9W 13 ² ON isa \ dz H

 9W NO H H

 13 6ia H H

 ID ID 6ia H H

 a 13 6ia H H

9W 9W 9W 619 HH t "90 / OOdfAI3 <I 29

 9W 3W 3W 919 H H

13 ^: J3 sia HH 13 [3 9ia HH ID 9W sia HH

 eia H H

 13 13 6H H H 13 89 H H 10 13 88 H H

13 88 H H

 89 H H

 ID za H H 13 i.9 H H

13 AS H H

 za H H

 ID 99 H H ID 13 93 H H 13 99 H H

 99 H H

13 HHH 13 ID HHH 13 3W HHH 3W 9W HHH 13 ^f; d3 69 HH

 13 ID "8 H

 ID 3W 918 H

 3W 3W 91H S3W- 1 H 13 91H H

 13 ID 919 H

 9W 10 3W gig H SH

^ Ze90 / 00df / X3d R36 HH B16 Me CI Me R36 HH B16 CI CI Me R36 HH B16 CFa CI Me R36 HH B19 Me Me Me R36 HH B19 Me CI Me R36 HH B19 CI CI Me R36 HH B19 CF ₃ CI Me R36 HH B29 CN NHCOMe Me R36 HH B31 NO 2 CI Me R36 HH B34 Me Me Me R36 HH B34 Me CI Me R36 HH B34 CI CI Me R36 HH B34 CFs CI Me R36 HH B35 CN NMe ₂ Me R36 HH B36 NO 2 CI Me R36 HH B37 CI Me Me R36 HH B38 MeO CI Me R36 HH B39 EtO MeS Me R36 HH B40 CN CI Me R36 HH B41 CN NH2 Me R36 HH B42 NO 2 CI Me R36 HH B43 NO MeO Me R36 HH B44 HH Me R36 HH B45 Me H Me R36 HH B46 Me Me Me R37 H 6-CI H Me Me Me R38 H 3- CI H Me CI Me R39 H 5-Me H CI CI Me R40 H 5, 6-Me H Me Me Me R40 HH B7 Me CI Me R41 H 3-Me H Me CI Me R42 H 6-Me ₂ NH H CI CI Me R42 HHH Me CI Me

(Table 2)

RR ¹ GBY, Y ₂ Y ₃

Rl H 5-Br HH Me Me

 R3 Ht Me nHexOCO H Br Et

R3 H U Me B8 Me Me Me

R4 H 2, 4-Me ₂ Nicotinol C1 Me Me

R5 H 2-Me- 5- MeCONH Picolinol C1 Me nBu

R6 H 5-EtO Isonicotinol Me H Me

R7 H 4-Cl-5-Me H Me MeS Me

R7 H 5-Me B7 Me Me Me

R8 H 5-Me H Me MeSO Me R9 H 2-Me Bl Me MeS0 ₂ Me

RIO HH B2 Me NO ₂ Me

Rll H 5-MeS nPenCO Me MeCONH Me

R12 HH B3 Me CI Me

 R14 H 2, 5-Ch B5 Et CI Me

R15 H 2- e-4-Br B6 nPr Br Me

R16 HH B7 CF ₃ Me ₂ C = N Me

R17 H 3, 5-C -l-Me B8 CN MeS Ph

R18 H 5-Me B9 CN CI Ph

R19 H U Me BIO Me Me Me

R20 H 1-Me Bll Et Me Me

R21 H l-Me-5-MeNH B12 Me MeO Me

R22 H 5-EtS B13 MeO CI Me

R23 H 5-nPr B14 nBuO H Me

R24 H 3-Br B15 H H Me

R25 H 5-Ph B16 Me Et Me

R33 H 4, 6-Me ₂ B7 CI Me Me

R33 H 4, 6- (MeO) ₂ B7 Me CI Me

R33 H H H CI H Me

R33 H H H Me CI Me

R33 H H H Me Me Me

R33 H H H Me H Me

R33 H H B6 CI H Me

R33 H H B6 Me CI Me

R33 H H B6 Me Me Me

R33 H H B6 Me H Me

R33 H H B7 CI H Me

R33 HH B7 Me CI Me D <U OJ cu cu U

 : S S S S S

 S ffi K DC S

SS J> S: SSUSSS

co oo

 ai c =: o¾ cd oi ai i

H 89

 3W ID 9W 919 H H 9CH

 H 13 919 H H

 aw H 68 H H

 89 H H

 9W 89H H 92H

13 3W 89 H H 9CH H ID 89 H H

 H A3 H H

3K Aa H H

 za H H

 13 za H H

 H 13 99 H H

 H 98 H H

 9W 99H H

 3W 13 9fl H H

 13 3N H H H

 H 13 H H H

 H 9W H H H

 3W 9W H H H

 ID 9N H H H

 aw H ID H H H

 H 3N H H H

 13 H H H

 13 88 H H

 H 88 H H

 H 89 H H

 A3 H H

13 HH sen 3W H 13 za HH l7ZC90 / 00df / X3d R36 HH B15 Et Me Me R36 HH B15 Me Me Me R36 HH Nicotival Me Me Me R36 HH Picolinol Me H Me R36 HH Isonicotinol CI H Me R36 HH B16 Me CI Me R36 HH B19 Et Me Me R36 HH B19 Me Me Me R36 HH B19 Me H Me R36 HH B19 CI H Me R36 HH B29 Me CI Me R36 HH B31 Et Me Me R36 HH B34 Me Me Me R36 HH B34 Me H Me R36 HH B34 CI H Me R36 HH B34 Me CI Me R36 HH B35 E t Me Me R36 HH B36 Me Me Me R36 HH B37 Me H Me R36 HH B38 CI H Me R36 HH B39 Me CI Me R36 HH B40 Et Me Me R36 HH B41 Me Me Me R36 HH B42 Me H Me R36 HH B43 CIH Me R36 HH B44 Me CI Me R36 HH B45 Et Me Me R36 HH B46 Me Me Me R37 HHH Me H Me R38 HHH CI H Me

R39 H H H Me CI Me

R40 H H H Et Me Me

R41 H H H Me Me Me

R42 H H H Me CI Me

(Table 3)

R ¹

R33 H 4, 6- (MeO) B7 Me Me R33 HHH Et Me R33 HHH Me CI 9

 Π a. U u

 Π Π a

9W u bQV

 Π u Π o a d] H fi Iff u u

 Π n & G a

9tti β

 U τ Lσ a u u

 n Π o G a J l J c τσ u u

 D I a n n o o a

] u

 I J O CM

 D l a n UN G oa

Q g

a J u COM n ^d lV UJ oca

 T Q a

 I J T COM

 1 J n I J

 T Q T a u

 n oa

C T

 a J a u

 L a Π n oa Ϊ CM

 n Π o oa

T a T

 1 J I J C T (T u

n CM n ooa JI nn coy

 og

 a J o a CM rl Π ooa og

 o a n COM n ooa

T on u u CM

L J o a n

 ί J 9IAf oa

 oa COM n n G Gil a J u COM

 La n n oa n n ooa l T

 J I J La ri COM n

 ΪΊ 9IAf La n n

 9l \ | aa u COM u a n n boa qa u

 u a n oy ooa

99 H H

 9W 93 H H

 13 13 H H H m

HN 3W HHHZ £ 90 / 00dT / 13d t¾

 o

 o

 CQ CP

 o

 K i l l

Cti CEi p≤; C¾ P≤ Pi Cii

R36 HH B7 CF ₃ Me R36 HH B8 Me CI R36 HH B8 CI CI R36 HH B8 Me Me R36 HH B8 CF ₃ Me R36 HH B9 Me CI R36 HH B15 CI CI R36 HH B15 Me Me R36 HH B15 CF ₃ Me R36 HH B15 Me CI R36 HH Nicotival CI CI R36 HH Picolinol Me Me R36 HH Isonicotinyl CF ₃ Me R36 HH B16 Me Me R36 HH B19 Me CI R36 HH B19 CI CI R36 HH B19 Me Me R36 HH B19 CF ₃ Me R36 HH B29 MeO CI R36 HH B31 Me Me R36 HH B34 Me CI R36 HH B34 CI CI R36 HH B34 Me Me R36 HH B34 CF ₃ Me R36 HH B35 Me CI R36 HH B36 CI CI R36 HH B37 Me Me R36 HH B38 CF ₃ Me R36 HH B39 Me CI R36 HH B40 CI CI R36 HH B41 Me Me R36 HH B42 CF; Me R36 HH B43 Me CI R36 HH B44 CI CI R36 HH B45 Me Me R36 HH B46 CF: Me

(Table 4)

R ¹ Y ¹

R33 4, 6-Me: H in!

 O H H

H3 ≡ R33 HHH CH≡CC H.SO H

R33 H 4,6- -Me B7 H H

R33 H 4,6--(MeO), B7 F H

R33 H H B7 CI H

R33 H H B7 Br H

R33 H H B7 Me H

R33 H H B7 Me Me

R33 HH B7 NH ₂ H

R33 H H B7 NHCOMe H

R33 H H B7 CN H

R33 H H B7 OH H

R33 H H B7 MeO H

R33 H H B7 EtO H

R33 H H B7 nPrO H

R33 H H B7 CHF.O H

R33 HH B7 CBrF ₂ 0 H

R33 H H B7 CFaO M

R33 H H B7 MeS H

R33 H H B7 MeSO H

R33 HH B7 MeS0 ₂ H

R33 H H B7 SH H

R33 H H-B7 EtS H

R33 H H B7 iBuS H

R33 H H B7 EtS H

R33 H H B6 iBuS H

R33 CI H B6 CI H

R33 Me H B6 Me H

R33 C0 ₂ Me H B6 MeO H

R33 NO 2 H B6 MeS H

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H

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H

H

 H pi as pi oi i oi csi

H

H

H

H

H 89

 H 3N H H 98H H ID H H

 H 929 H H

 H 13 989 H H

 H 3 58a H H

 H ID ^ ga H H

 H 3W ea H H

 H 13 zza H H

 H 3W H H

 H 13 619 H H

 H 6ia H H

 H 13 5ia H H

 H 3W 63 H H

 H 13 69 H H

 H 89 H H

 H ID 89 H H

 H H H

 H 13 Aa H H

 H 98 H H

 H n 99 H H

 H sa H H

 H ID 99 H H

 H H H H

 H 10 H H H

 H H H H H H H H

 H 0 H3 H H H

 H H H H

H oia HHH 9S¾ Z £ 90 / 00dT / 13d R36 HH 2-Cl-PhCO CI H

R36 H H 3-Cl-PhCO Me H

R36 H H 4-Cl-PhCO CI H

R36 H H Me H

R36 H H CI H

R36 H H 2-F-PhCO Me H

R36 H H 2, 6-F-PhCO CI H

(Table 5)

R

RR ¹ GBA

R3 H Me B7 Al

 R7 H H B7 Al

 RIO H H B7 Al

 R12 H H B7 Al

 R20 H 1-Me B7 Al

 R22 H 5-Me B7 Al

R24 H 5— Me B7 Al 01

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2V ia ia-ε H

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 IV za 13-ε H

 IV za H

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 OIV 8 H H

 OIV Α9 H H

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 OIV za H H

 OIV H H ΟΐΗ OIV H H OIV H H OIV Aa H H

 OIV za H H

 OIV za H H

 OIV a H H

 OIV za H

 OIV H H OIV H H

 6V H H

 6V H H

 8V H H

 8V Aa H H zv H H zv ia H H

 9V H H

 9V za H H

 9V H H

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 0IV a H H on οιν Z9 H H οιν AH H H οιν a H H- i

0IV H

 01V za H

 0IV za H H

 01V za H H οιν za 3W-1 H οιν za 3 -1 H ιε¾

01V za H

 0IV AH H

 01V H H οιν H H οιν za H H

 0IV H H

 01V za 3W-9 H

 01V H H

 0IV a 3 -S H οιν za H H οιν za 3W— I H

Z £ 90 / OOdT / 13d A8 HH

 OZV A3 H H

 02V Aa H H

 61V za H H

 61V ia H H

 81V za H H

 81V a H H

 MV ia H H

 LIV za H H

 9tV H H

 91V H H

 91V za H H

 SIV H H H H

 ^ IV H H gIV H H ειν a H H

 i \ v za H nv A3 H ziv H l ^ z \ v A3 3W-9 H nv H ziv a H H ziv H H Olil z \ v H H ziv H nv za 13-C H nv za H nv 3W-S H

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 H H

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 m H H m 9 H H

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 H

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R36 HH B7 A57 When applying the compound of the present invention, it is usually mixed with a suitable solid carrier or liquid carrier, and further, if desired, a surfactant, a penetrant, a spreading agent, a thickener, a cryoprotectant, a binder , Anti-caking agent, disintegrant and decomposition inhibitor, soluble concen trate, emulsion (emulsi fable concentrate), wet table powder, τΚ solvent (water soluble powder) , Water dispersible granule, water soluble granule, suspension concentrate., Emaulsion, oil in water, suspoemarezi, suspoemulsion, My Practical use in preparations of any dosage form such as chloe margillon (microm lion), powder (dustable powder), granule (granule) and gel (gel)

Can be In addition, from the viewpoint of labor saving and improvement of safety, the preparation of any of the above dosage forms can be provided by being enclosed in a water-soluble package.

 Examples of the solid carrier include natural minerals such as quartz, kaolinite, pyrophyllite, celite, talc, bentonite, acid clay, agar pulgite, zeolite and diatomaceous earth, calcium carbonate, ammonium sulfate, and sulfate. Inorganic salts such as sodium and chlorinated lime, synthetic silicic acid, and synthetic silicate. Examples of the liquid carrier include alcohols such as ethylene glycol, propylene glycol, and isopropanol; aromatic hydrocarbons such as xylene, alkylbenzene and alkylnaphthalene; ethers such as butyl sorbet; ketones such as cyclohexanone; Esters such as tyrolactone; acid amides such as N-methylpyrrolidone and N-octylpyrrolidone; vegetable oils such as soybean oil, rapeseed oil, cottonseed oil and castor oil; and water.

 These solid and liquid carriers may be used alone or in combination of two or more. Examples of the surfactant include nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyl, polyoxyethylene polyoxypropylene block copolymer, polyoxyethylene fatty acid ester, sorbitan fatty acid ester, and polyoxetylene sorbin fatty acid ester. , Alkyl sulfate, alkyl benzene sulfonate, lignin sulfonate, alkyl sulfosuccinate, naphthylene sulphonate, alkyl naphthylene sulphonate, naphthylene sulphonic acid Salt of formalin condensate of lensulfonic acid, polyoxyethylene alkylaryl ether sulfate and phosphate, polyoxyethylene styryl phenyl ether sulfate and phosphate, polycarboxylate And Anion surfactants such as polystyrene sulfonic acid salts, and cationic surfactants, as well as amino acid type and amphoteric surfactants such as betaine type, such as alkylamine emissions salts and alkyl quaternary Anmoniumu salt.

The content of these surfactants is not particularly limited. Usually, the range of 0.05 to 20 parts by weight to 100 parts by weight is desirable. These surfactants may be used alone or in combination of two or more.

 When the compound of the present invention is used as a pesticide, other types of herbicides, various insecticides, acaricides, nematicides, fungicides, fungicides, plant growth regulators may be used as needed when formulating or spraying. It may be used in combination with synergists, fertilizers, soil conditioners, etc.

 In particular, by mixing with other pesticides or plant hormones, it can be expected to reduce costs by reducing the amount of applied drugs, expand the insecticidal spectrum by synergistic action of the mixed drugs, and achieve a higher pest control effect. At this time, a combination with a plurality of known agricultural chemicals is possible at the same time. Examples of the kind of agrochemical used in combination with the compound of the present invention include compounds described in Farm 'Chemicals', Nodbook (Farm Chemicals Handbook, 1994). Specific examples of the common names are as follows, but are not necessarily limited thereto.

Fungicides: acibenzolar-S-methyl, acylaminobenzamide, ambam, ampropyfos, ampropyfos, anilazine, azaconazole, azaconazole (Azoxystrobin), benalaxyl (benalaxyl), benodanil (benodani 1), benomyl (benomyl), benthiazole (benthiazole), benzamakirire (benzamacr i 1), binano ヽ ° cririll (binapacryl), bifuko nirire ( biphenyl), bitertanol, bethoxazine, bordeaux mixture, blast icidin-S, bromoconazole, bupirimate, buthiobate Calcium polysul fide, capta follie, capta fol) , Captan, copper oxychloride. Carpropamid, carbendazim, carboxin, CGA-279202 (test name), chinomethionate , Clobenchiazone (chlobenthiazone), chlorfenazol (chlorfena zol), chloroneb (chloroneb), chlorothalonil (chlorothaloni 1), clozolinate (chlozol inate), kufuranebu (cuf raneb), simoxanil (cymoxani 1), cyproconazole (cyproconazol), cyprodinirile (cyprodinil), cyprofuram (cyprofuram, evening, 'zometto (dazomet), anodocarireb (debacarb), dichlorophen, diclobutrazol (die lobutrazol) ), Dichlofuranide (die lhlofluanid), diclomedine (diclomedine), dichlorane (dicloran), jetfencalireb (diet ofencarb), diclosymet (diclocymet), difenoconazo, difumetorim, diflumetor Dimethirimol (dimethirimol), dimethomorph (dimethomorph), diniconazoline (diniconazole), diniconazole M (diniconazole-M), dinocap (din ocap), diphenylamine (diphenylamine), dipyrithione (difolimos) The dithianon, dodemorph ph), dodine (dodine), drazoxolon (drazoxolon), edifenofos (edi fenphos), epoxyconazo 'epiriconazole', eyconazo'rile, etacona zole, ethirimol, etrimoline famoxadone), fenarimol, febuconazole, fenamidone, fendazoslam, fenfuram, fenhexamid, fenpicloni, fenpicloni (Fenpropidin), fenpropimorph

(fenpropimorph), fentin (fentin), ferban (ferbam), ferimzone (ferimzone), fluazinam (fluazinam), fludioxonil (fludioxoni 1), fluorimide (fluoroimide), fluquinconazole (fluquinconazole), flusilazole amide (flusilazole) Flusul famide), Flutolanil, Flutriafol, Folpet, Fospet-aluminium, Fuberidazole, Furaxyl, Furametpyr ), Guazatine, hexachlorobenzene, hexaconazole, hexaconazole, hymexazol, imazalire (imazali 1), imibenconazole, iminoconad, imibenconazole ine) Ibuconazole, iprobenfos, iprodione

(iprodione), isoprothiolane (isoprothiolane), ipprovalicarp (ipr oval icarb), kasugamycin, kresox im-methyl, mankatsuno, ⁰ — (mancopper), mancozeb, maneb

(maneo, meno, ° dipyrim (mepanipyrim), mepronil (mepronil), metalaxyl (metalaxyl), metconazole (metconazole), metasulfocarb (meta sulfocarb), metiram (metiram, metominostrobin) Microclobanil (myclobutanil), MTF-753 (test name), nabam, nickel bis (dimethyldithiocarb bamate), nitrotar-isopropyl (ni trotha triisopropyl), narimol

(nuarimol), NNF-9425 (test name), octilinone (oc thi 1 inone), ofurese (ofurace), oxadixyl (oxadixyl), oxycarboxin (oxycarb oxin), oxpoconazole fumarate (oxpoconazole fumarate) ), Efurzoate), penconazolile enconazole), penciclone (pencycu ron), phthalide, phthalide, piperaline, polyoxins, potassium ium hydrogen carbonate, pro Probenazole, prochloraz, procymidone, propamocarb hydrochloride, propiconazole

(.propi conazole), Frobineb (propineb), Hirasophos (pyrazophos), Pyrifenox (pyrifenox), Pyrimethanil (pyrimethani 1), Pyrocuron (pyroqui Ion), quinomethionate en. ), Quintozene, RH7281 (test name), sodium hydrogen carbonate (sodium hydrogen carbonate), sodium hypochlorite (sodium hypochlorite), sulfur (sulfur), spiroxamine (spiroxamine), tebuconazole ( tebuconazol e), technazene, tetraconazole, tetraconazole, thiabendazole, thiadiazin / mi lneb, thifluzamide

(thi f luzamide), thi ophanate-methyl, thiram

(thiram), tolclofos-methyl, tolylfluanid, triadimefon, triadimefon, triadimenol, triazoxide, triazoxide, tricyclazole Lidemorph (tridemorph), triflumizole (tri flumizole), triforine (triforine), triconazole (tr it iconazole), validamycin (val ida mycin), vinclozol in (vinclozol in), sulphite Uzinc sulfate), zineb

 (zineb), ziram and shiitake mycelium extract.

 Bactericides: streptomycin, tec loftalam, oxyterracycline, oxolinic acid, and oxolinic acid.

 Nematicides: aldoxycarb, cadusafos, fosthiazate, fosthietan, oxamyl and fenamiphos.

 Acaricides: acequinocyl, amitraz, bifenazate, bromopropylate, bromopropylate, chinomethionat, chlorobezi late, clofenezine cl , Cyhexatine, dicofol, dienochlor, etoxazole, fenazaquin, fenbutatin oxide, fenpropathrin, fenpropathrin (Fenproximate), hal fenprox (halfenprox), hexity thiazox (hexy thiazox), mirbe pectin (mi lbemect in), propargite (propargite), pyridaben (pyrid aben), pyrimidifen (pyrimidi ien) and tefufenpyrad enpyrad).

Insecticides: abamectin, acephate, acetamipirid, aldicarb, allethrin, allezrin, zinphos-methyl, bendiocarb, bendiocarb (Benfuracarb), bensultap, bifenthrin, buprofezin, buprofezin, butocarb oxim, carbaryl, carbaryl, carbofuran, carbosul fan, carbosul fan, carbosul fan, Chlorefenapyrile (chlorfenapyr), Chlorpyrifos (chloi ^ pyrifos), Chlorfenvinphos (chlorfenvinph os), Chlorfluazuron (chlorfluazuron), Clothianidi (clothianidi) n), chromafenozide, chromapyri fos-methyl, cycloprothrin, cyfluthrin, cyfluthrin, beta-cyfluthrin, cypermethrin cypermethrin (cyromaz ine), sizzle, rothalin (cyhalothr in), ram evening, 'Ishino, rothrin (lambda-cyhalothrin), deltamethrin (deltamethrin), diaf enthiuron (diaf enthiuron), diazinon (diazinon), diacloten (dia clo) Diflubenzuron, dimethylv inphos, diofenolan, disul foton, dimethoate, emamectin-benzoatej, EPN, Esfenvalerate, ethiofen carb, Chipuroru (ethiprole), etofenprox (etofenprox), E Torimuhosu (etrimfos), Fuenitorochion (feni trothion), Fuenobukarupu

(fenobucarb), fenoxycarb, fenpropatrin (fenpropathr in), fenvalerate, fenvalerate, fipronil, uacrypyrim, flueythrinate, flufenoxuron, flufenoxuron Prox (flufenprox), evening aufluvalinate (tau-fluvalinate), honofos (fonophos), forme evening (formetanate), formothion (formothion), furatiokarpu (furat iocarb), nose, mouth fenofide (halofenozide) Oxaflumuron (hexaf lumuro n), hydramethylililenone (hydramethylnon), imidacloprid (imidacloprid), isofenphos (isofenphos), indoxacarb (indoxacarb), isoprocarb (isoprocarb), isoxathion (lufenu) ron), malathion, metalaldehyde, methamidophos

(methamidophos), methidathion, methacrifos, metalcalp, metalcarb, methomyl, mesoprene, methoxychlor, methoxyphenozide, monocrotophos monocrotophos), muscalure, nidinotefuran, nitenpyram, and nits

(omethoate;, oxydemeton-methyl), oxamilile (oxamy 1), / lathion (parathion), parathion — methy 1, permethrin, phenthoate, foxim

, Phoxim), holate phoratej, hosalon, phosmet, phosphamidon, pirimicarb, pirimicarb, pirimiphos-methyl, profenofos, profenofos Protri fenbute, pymetrozine, pyraclofos

^ pyrac lofos;, pyriproxyfen (, pyr iproxy fen), rotenone (rotenone), sulprofos (sulprofos), silafluofen (silafluofen), spinosad

(.spinosad), sul fotep, teffenozide, tefiubenzuron, tefluthrin, terbufos

(terbufos), tetrachlorovinphos, thiacloprid

(thiacloprid), thiocyclam (thiocyclam), thiodicarb (thiodicarb), thiamethoxam (thiamethoxam), thiofanox (thiofanox), thiometon

(thiometon), tolfenpyrad (to 1 f enpyrad), tiger mouth methrin (tralomet hrin), trichlorfon, triazuron, triflumuron and vamidothion.

 The amount of the applied compound of the present invention varies depending on the application scene, application time, application method, cultivated crops, etc., but generally 0.005 to 50 kg per hectare (ha) is appropriate as the amount of the active ingredient. .

 Formulation examples of preparations using the compound of the present invention are shown below. However, the composition examples of the present invention are not limited to these. In the following formulation examples

"Parts" means parts by weight.

 (Wettable powder)

Compound of the present invention Q. 1 to 80 parts

Solid carrier 5 to 98.9 parts

Surfactant 1 to 10 parts

Others 0-5 copies

 Other examples include an anti-caking agent and an anti-decomposition agent.

(Milk) 0.1 to 30 parts of the compound of the present invention

Liquid carrier 45 ~ 95 5 parts

Surfactant 4.9 ~; L 5 parts

Others 0 to 10 copies

 Other examples include spreading agents, decomposition inhibitors and the like. (Suspension)

0.1 to 70 parts of the compound of the present invention

Liquid carrier 15 to 98.89 parts

Surfactant 1 to 1 2 parts

Other 0.01 to 30 parts

 Other examples include an antifreezing agent and a thickener. (Granular wettable powder)

0.1 to 90 parts of the compound of the present invention

Solid carrier 0-98.9 parts

Surfactant 1 to 20 parts

Others 0 to 10 copies

 Other examples include a binder and a decomposition inhibitor. (Solution)

Compound of the present invention 0.01 to 70 parts

Liquid carrier 20 to 99.99 parts

Others 0 to 10 copies

 Other examples include an antifreezing agent and a spreading agent. (Granules)

Compound of the present invention 0.01 to 80 parts

Solid carrier 10 to 99.99 parts

Others 0 to 10 copies

 Other examples include a binder and a decomposition inhibitor. (Powder)

Compound of the present invention 0.01 to 30 parts Solid carrier 65 to 99.99 parts

Others 0-5 copies

 Other examples include an anti-drift agent and an anti-decomposition agent.

 Next, a more specific example of the formulation of a pest control agent comprising the compound of the present invention as an active ingredient is described below. The present invention is not limited to these.

 In the following formulation examples, “parts” means parts by weight.

 [Formulation Example 1] wettable powder

Compound of the present invention No. 1 25 parts

Pyrolite 7 1 copy

Solpol 5039 2 parts

 (Mixture of nonionic surfactant and anionic surfactant: trade name of Toho Chemical Industry Co., Ltd.)

Rikiichi Plex # 80D 2 copies

 (Synthetic hydrous silicic acid: Shionogi & Co., Ltd. product name)

 The above is uniformly mixed and ground to form a wettable powder.

 [Formulation Example 2] Milk

Compound No. 15 of the present invention, 5 parts

Xylene 75 parts

 N-methylpyrrolidone 15 parts

Solpol 2680 5 parts

 (Mixture of nonionic surfactant and anionic surfactant: Toho Chemical Industry

(Product name)

 The above are uniformly mixed to form an emulsion.

 [Formulation Example 3] Suspension (Floable)

Compound of the present invention No. 1 25 parts

Agrizole S—7 10 1 0 parts

 (Nonionic surfactant: Kao Corporation)

Lunox 1 000 C 0.5 part

(Anionic surfactant: trade name of Toho Chemical Industry Co., Ltd.) Xanthan gum 0.2 parts

Water 64. 3 parts

 After uniformly mixing the above, wet pulverization is performed to obtain a suspending agent.

 [Formulation Example 4] Water dispersible granule (dry flowable)

Compound of the present invention No. 1 75 parts

Hytenol NE-15 15 parts

 (Anionic surfactant: Daiichi Kogyo Pharmaceutical Co., Ltd.)

Vanilex N10

 (Anionic surfactant: Nippon Paper Industries Co., Ltd.)

Carplex # 80D 1 0

 (Synthetic hydrous silicic acid: Shionogi & Co., Ltd. product name)

 After uniformly mixing and pulverizing the above, a small amount of water is added, followed by stirring, mixing and kneading, and the mixture is granulated by an extrusion granulator and dried to obtain a wettable powder.

 [Formulation Example 5] Granules

Compound No. 15 of the present invention, 5 parts

Bentonite 50 parts

Talc 45 parts

 After the above mixture is uniformly mixed and pulverized, a small amount of water is added, and the mixture is kneaded with stirring, kneaded, granulated by an extruder and dried to obtain granules.

 [Compounding Example 6] Powder

Compound of the present invention No. 1 3 parts

Carplex # 80D 0.5 part

 (Synthetic hydrous silicic acid: Shionogi & Co., Ltd. product name)

Kaolinite 95 parts

1.5 parts of diisopropyl phosphate

 The above is uniformly mixed to form a powder.

For use, the above wettable powders, emulsions, flowables, and particulate wettable powders are diluted 50 to 20,000 times with water and dispersed so that the active ingredient is 0.005 to 50 kg per hectare (ha). . BEST MODE FOR CARRYING OUT THE INVENTION

 Hereinafter, synthesis examples and test examples of the compound of the present invention will be specifically described as examples, but the present invention is not limited thereto.

 [Synthesis Example 1] Synthesis of 3- (4-chloro_1,3-dimethylvirazol-5-yl) -3-hydroxy-2- (2-pyrazinylthiazol-4-yl) acrylonitrile ( Compound No. 1 1)

 Add 2.00 g of 4-cyanomethyl-2-pyrazinylthiazole and 2.44 g of 4-chloro-1,3-dimethyl-5- (1-pyrazolylcarbonyl) pyrazole to 50 ml of dry tetrahydrofuran, and stir with ice-cooling. 2.22 g of potassium t-butoxide were added. After stirring for 30 minutes under ice cooling, 5 Om 1 of ice water was added, and the mixture was neutralized with 1 N hydrochloric acid. After extraction with 1 butanol 5 Om1, the organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain a crude product. This was washed with isopropyl ether and dried to obtain 1.90 g of the desired compound.

Melting point: 228.5-230. O :.

 [Synthesis Example 2] Synthesis of 3- (4-chloro-1,3-dimethylpyrazole-5-yl) -3-bivaloyloxy-2- (2-pyrazinylthiazol-4-yl) acrylonitrile (Compound No. 12)

 0.1 g of 60% sodium hydride was washed with n-hexane and 2 Oml of dry tetrahydrofuran was added. Under ice-cooling and stirring, slowly add 0.60 g of 3- (4-chloro-1,3-dimethylpyrazole) —3-hydroxy-2- (2-pyrazinylthiazo-1-yl 4-yl) acrylonitrile After the addition, the mixture was stirred at room temperature for 1 hour. 0.25 g of pivaloyl chloride was added dropwise, and the mixture was further stirred for 6 hours. The reaction solution was poured into ice water, extracted with 5 mL of ethyl acetate, the organic layer was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain a crude product. This was washed with isopropyl ether to obtain 0.49 g of the desired compound.

Melting point: 1 78-1 79.

The structures and melting points of the compounds of the present invention synthesized according to the above scheme or the above synthesis examples are shown in Tables 6 to 10, but those not particularly mentioned are mixtures of E-form and Z-form. The abbreviations in the table have the same meaning as described above. (Table 6)

o. RR ¹ GBA Melting point (° C), isomer ratio

1 R16 H H B7 A10 1 29. 5-131, E-form or Z-form

2 R16 H H B7 A10 Resin, E / Z mixture

3 R16 H H H A10

 R36 H H H A2 230-231

 5 R36 H H B7 A2 124-128, E / Z mixture

6 R36 H H H A3 209-210

 7 R36 H H B7 A3 180-181. 5, E / Z mixture

8 R36 H H H A4 218-221

 9 R36 H H B7 A4 194-195.5, E-form or Z-form 0 R36 HH B36 A10 184-185, E-form or Z-form 1 R36 H H H Al l 228.5-230

2 R36 H H B7 All 178-179, E-form or Z-form 3 u π n R7 Resin, 1 1

4 R36 H H H A25 235-237

5 R36 H H B7 A25 125-128, E-form / Z-form mixture 6 R36 HH B7 A25 157-157.5, E-form or Z-form 7 R36 HH H A27 214-215

8 R36 H H B7 A27 149-150, 8 7/6

9 R36 H H H A31 273-274.5

0 R36 HH B7 A31 157-159, E / Z mixture (Table 7)

No. RR ^] GBA Melting point (° C), Isomer ratio 1 R12 HHH A2 224.5-226

 22 R12 H H B7 A2 70-72 E body or body

23 R12 H H H A10 128.5-131

 24 R12 H H B7 A10 211-213, E-form or Z-form 5 R17 H l-Me-5-Cl H A2 238-243

(Table 8)

No. A Melting point (° C), Isomer ratio

26 Rl H H H All Resinous

 27 Rl H 5-Me H All Resin

 28 Rl H H B7 All Resin

 29 Rl H 5-Me B7 All resinous

 30 R3 H 1-Me H A10 Resin-like

 31 R3 Hot Me B7 A10 Resin, E or Z

32 R3 H 1-Me B7 A10 Resin, 1/2

 33 R7 H 5-Me B7 A2 Resin, E or Z

34 R7 H 5-Me B7 A10 Resin, E-form or Z-form RIO H 2, -diMe H All resinous

 RIO H 2,4-diMe B7 All resinous

 R12 H H H Al 127-128

 R12 H H B7 Al 172-173, E or Z

R12 H H H A2 165.8-169.3

 R12 H H B7 A2 Resin-like.

 R12 H H H A3 133-134

 R12 H H B7 A3 124-125, E or Z

R12 H H H A4 Resin

 R12 H H B7 A4 Resin, 1 9

 R12 H H H A10 Resin-like

 R12 H H B7 A10 127-128.3, E or Z

R12 H H H All 69.8-72.1

 1

 R12 H H B7 All Resin, 1 9

 R12 H H B7 A18 138.2-140.7, Z body

 R12 H H B7 A24 Resin, 1 7

 R12 H H H A25

 R12 H H B7 A25 103-104, E or Z

R12 H H B7 A25 Resin, Z-form or E-form

R12 H H B7 A32 Resin, E or Z

R12 H H H A45 188-189

 R12 H H B7 A45 101-102, E or Z

R12 H H H A48 139-141

 R12 H H B7 A48 Resin, E or Z

R12 H H H A58 resinous

 R12 H H B7 A58 Resin, 2/3

 R12 H H B7 A58 Resin, E-form or Z-form

R12 H H H A59 199-200.5

R12 HH B7 A59 117.5-119, E or Z 12 HH B7 A59 121-122, Z or E

R12 H H B7 A60 Resin, 1 3

 R20 H Me Me H A3 141-143

 R20 H 1-Me B7 A3 119-122, E-form or Z-form

R20 H 1-Me H AlO 236-237

 R20 H 1-Me B7 AlO Resin, E / Z mixture

R20 H 1-Me H A25 242-243

 R20 H 1-Me B7 A25 119-120, E or Z

R33 H H B7 AlO Resin, E or Z

R34 H H B7 AlO Resin, 1Z2

 R36 H H H A4 177.5-180

 R36 H H B7 A4 145-146, E or Z

R36 H H H AlO Resin-like

 R36 H H Me AlO Resin, E or Z

R36 H H C (0) (3--lysyl) AlO 166-172, E-form or Z-form

R36 H H B3 AlO Resin, E or Z

R36 H H B6 AlO 135-151, 2/1

 R36 H H B7 AlO resin

 R36 H H B34 AlO Resin, 2 1

 R36 H H B36 AlO 147-151, E-form or Z-form

R36 H 3-Et H AlO resinous,

 R36 H 3-Et B7 AlO 115.2-117.1 E-form or Z-form

R36 H 3-Et B7 AlO Resin, 1/9

 R36 H 3-Me B7 A2 Resin, E or Z

R36 H 3-Me B7 AlO Resin, 1 1

 R36 H H H All 294-296

 R36 H H B7 All 130-131.5, E or Z

R36 H H B7 A25 97-99, E / Z mixture

R36 HH B7 A25 133.5-134, E or Z 93 R36 HH A27 261-265

(Table 9)

 R -N CN

 'N

0-B

No. R Ri G B A Melting point (° C), isomer ratio

94 R12 Me H H A2

 95 R12 Me H B7 A2 Resin

 96 R12 Me H H A10 166.3-167.9

 97 R12 Me H B7 A10 Resin-like

 98 R12 H H B7 A10 Resin

No. RR ¹ GBA Melting point (° C), isomer ratio

99 R3 Hot Me H A10 158.2-160.3

 100 R3 H 1-Me B7 A 10 Resin, 9 no 1

 101 R3 Hot Me B7 A10 Resin, 1-9 Next, the usefulness of the compound of the present invention as a pesticide will be specifically described in the following test examples.

In addition, as a comparative compound, the following compound A described in WO9494493, B and C were used.

 Compound C

[Test Example 1] Insecticidal test against tobacillus power

 A 5% emulsion of the compound of the present invention described in the specification (25% wettable powder is used depending on the compound) is diluted with water containing a spreading agent to give a drug solution having a concentration of 100 ppm or 500 ppm. Prepared.

 A sufficient amount of this chemical was sprayed on the foliage of rice planted in a pot of 1Z20,000. After air-drying, the cylinder was set up, 10 larvae of the second instar larvae of the flying pills were released per bot, capped, and stored in a constant temperature room. The survey was conducted 6 days later, and the mortality was calculated by the following formula. The test was conducted in two wards.

 Mortality (%) = [Number of dead insects / (Number of dead insects + Number of surviving insects)] x 100

 As a result, the following compounds showed a mortality of 80% or more at a drug solution concentration of 500 ppm.

 Compound No. of the present invention: 1, 24, 5, 6, 10, 11, 11, 12, 13, 18, 20, 28, 37, 38, 39 40, 41, 42, 45, 46, 47, 48 , 49, 50, 51, 52, 53 54, 55, 56, 78, 79, 80, 81, 82, 83, 88, 89 90, 95, 97, 98.

Table 11 shows the results of comparison with Compounds A, B and C. [Table 11] Mortality (%)

Compound

 NO. Chemical concentration

 500ppm 100 prescription

46 100 90

 A 9 0

 B 10 0

 C 10 0

[Test Example 2] Insecticidal test against black leafhopper

 Rice foliage is immersed in an emulsion of the compound of the present invention at a concentration of 100 ppm or 500 pm for about 10 seconds, and the foliage is placed in a glass cylinder to release an adult leafhopper, which is resistant to an organophosphorus insecticide. Then, it was put in a thermostat at 25 ° C with a lid with a hole, and the number of dead insects was investigated after 6 and the mortality was calculated from the same formula as in Test Example 1. The test was conducted in two wards. As a result, the following compounds showed a mortality of 80% or more at a drug solution concentration of 500 ppm.

 Compounds of the present invention No. 1, 2, 3, 4, 5, 6, 10, 10, 11, 12, 13, 17, 18, 18, 19, 20, 21, 22, 23, 28, 29, 30, 3 1, 32, 3

7 38 39 40 41, 42, 43, 44, 45, 46, 47, 48, 4 9 5.0 5 1 52 53, 54, 55, 56, 58, 74, 75, 76, 7 8 79 80 8 1 82, 83, 84, 87, 88, 89, 90, 94, 9 5 96 97 98

Table 12 shows the results of comparison with Compounds A, B and C. [Table 12] Mortality (%)

Compound

 NO. Chemical concentration

 500ppm 100 prescription

46 100 100

 A 20 0

 B 0 0

 C 0 0

[Test Example 3] Insecticidal test against peach aphid

 Wet filter paper was spread on a glass dish with an inner diameter of 3 cm, and cabbage leaves of the same diameter were placed on top of it. Four adult wingless female peach aphids were released, and one day later, a chemical solution was sprayed (2.5 mg / cm2) using a rotary spray tower. The drug solution was prepared by diluting a 5% emulsion of the compound of the present invention described in the specification (25% wettable powder for some compounds was tested) with water containing a spreading agent to a concentration of 100 ppm or 500 ppm. Was used. Six days after the treatment, adult and larval mortality was determined from the following formula. The test was performed in two sections.

 Mortality (%) = [Number of dead insects (Number of dead insects + Number of surviving insects)] X 100

As a result, the following compounds showed a mortality of 80% at a chemical concentration of 5 OO pm. Compound of the present invention No. 1, 2, 3, 4, 5, 67, 8, 9 10 1 1 1 2, 13, 14, 15 15 16 17 18 1, 19 20, 21 22 23 2

4 26 27 28 29 30 3 1 32 33 34 35 36 3 7 38 39 40 41 42 43 44 45 46 47 48 4 9 50 5 1 52 53 54 55 56 57 58 59 60 6 1 62 63 64 65 67 72 73 74 7 5 76 77 7 8 7 9 80 8 1 82 83 84 85 86 87 88 89 9 0, 91, 92, 93, 94, 95, 96, 97, 98.

 Table 13 shows the results of comparison with Compounds A, B and C.

 [Table 13] Mortality (%)

Compound

 NO. Chemical concentration

 500ppm lOOppm

46 100 100

 0 0

 B 89 0

 C 72 0

[Test Example 4] Contact insecticidal test for Japanese moth

 The perilla leaves are immersed for about 10 seconds in an aqueous emulsion of the compound of the present invention at a concentration of 100 ppm or 500 ppm, air-dried, and placed in a petri dish. Then, it was put in a constant temperature room at .25 with a lid with a hole, and the number of dead insects after 6 days was investigated. The mortality was calculated from the same formula as in Test Example 1. The test was performed in two ward systems. As a result, the following compounds showed a mortality of 80% or more at a drug solution concentration of 5 O Oppm.

 Compounds of the present invention No. 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 10, 11, 12, 13, 14, 14, 15 16, 17, 18, 19, 20 , 26, 30, 3 1, 37, 38, 39, 40 41, 42, 43, 44, 45, 46, 48, 49, 51, 52, 53, 54 5 5, 56, 63, 74, 75, 76, 78, 79, 80, 81, 82, 83 94, 95, 96, 97, 98.

Table 14 shows the results of comparison with Compounds A, B and C. [Table 14] Mortality (%)

Compound

 NO. Chemical concentration

 500 doors lOOppm

46 100 100

 A 20 0

 B 27 0

 C 0 0

[Test Example 5] Insecticidal test against periwinkle

 A 5% emulsion of the compound of the present invention described in the description (25% wettable powder for some compounds) was diluted with water containing a spreading agent to prepare a drug solution having a concentration of 500 ppm. Then, immerse the cucumber leaves in this solution for about 10 seconds, air-dry them and put them in a Petri dish.In this, release 10 larvae of the second order larvae per petri dish, cover them, and keep them constant at 25 ° C. After being housed in the room, the mortality after 6 days was determined from the same formula as in Test Example 1. In addition, the test was performed in two sections.

 As a result, the following compounds showed 100% mortality.

 Compound of the present invention No .: 1, 2, 4, 5, 6, 8, 9, 10, 10, 11, 12, 13, 14, 15, 16, 17, 17, 18, 19, 38 , 39, 41, 42, 45, 46, 49, 51, 52, 53, 55, 56, 64, 80, 83, 89, 90, 91, 92, 9 3ο

 [Test Example 6] Acaricidal efficacy test on Nami-nada

Leaves green beans cut to a circular size 3. 0 cm using a leaf punch was placed on the wet filter paper on the polystyrene cup diameter 7 c _m. Two larvae of the lobster were inoculated into each of the 10 larvae per leaf. A 5% emulsion of the compound of the present invention described in the specification (25% wettable powder was used depending on the compound) was diluted with water containing a spreading agent and concentrated at 500 ppm. And sprayed the solution at a rate of 2 m per styrene cup using a rotary spray tower, stored in a thermostatic chamber at 25 ° C, and measured the mortality after 96 hours as in Test Example 1. It was determined from a calculation formula. In addition, the test was performed in two sections. As a result, the following compounds showed a mortality of 80% or more.

 Compound No. of the present invention: 1, 2, 3, 4, 56, 7, 8 10 12 13

14, 1 5, 16 1 8, 26, 27, 28 29, 3 1 32 33 34,

35, 36, 38 39, 40, 42, 43 44, 45 46 47 48,

49, 50, 52 53, 56, 58, 67 69, 7 1 72 74 7 5, 76, 78, 79 80, 81, 82, 83 85, 86 88 89 90, 94, 95, 96 97, 98. Over the years of use of insecticides and fungicides, pests have recently become resistant and difficult to control with conventional insecticides and fungicides. Some pesticides are highly toxic and some are disturbing ecosystems due to persistence. Therefore, the present invention provides a novel insecticide or fungicide with low toxicity and low residue, and an agent for preventing adhesion of aquatic organisms to water with little effect on ecosystems and secondary pollution.

Claims

The scope of the claims

1. Equation (1):

[Where,

Q is R, and (R ¹⁾ thiazolyl substituted with _n or R and (pyrazolyl substituted with R Li _n,,

 A is phenyl optionally substituted with W, naphthyl optionally substituted with W or heterocyclic group optionally substituted with Y (however, this heterocyclic group is phenyl, furyl, pyrrolyl, Oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-isoxaziazolyl, 1,2,4-oxoxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4- Triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4 _Triazinyl, indazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, quinoxalinyl, phthalazinyl, cinnolinyl Or quinazolinyl.)

The B, H, (:, ~ (: 4 alkyl, C, -C ₄ haloalkyl, C ₂ ~ (: substituted by ₄ Arukokishia _{alkyl, CH 3 S CH a, CH} 3 OC 2 H 4 〇_CH R ^a C, ~ C ₄ alkyl Le, Ci～C ₄ alkyl substituted with R ^b, tetrahydrophthalic Vila _{sulfonyl, (CH 3) 3 S i} , CL alkylsulfonyl, halogen or C, optionally substituted with -C ₄ alkyl Good phenylsulfonyl, _S〇 ₂ CF ₃ , (:!-Monoalkylaminosulfonyl, C ₂ -C ₈ dialkylaminosulfonyl, phenylaminosulfonyl, C ₂ -C ₅ monoalkylaminothiocarbonyl, C _3- C ₉ dialkylaminothiol pyridine, Cs Cs cyanoalkyl, C ₃ -C ₉ alkoxycarbonylalkyl, — C (= 〇) T -P (= 0) T ² T ³ , one P (= S) T ² T ³ , alkali metal atoms, Al earth metal atom or NHT ⁴ T ⁵ T ^fi

 R is a heterocyclic group which may be substituted with G (provided that the heterocyclic group is furyl, piaryl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxaziazolyl, 1 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2 , 3,4-tetrazolyl, pyrimigel, pyrazinyl, pyridazinyl, 1,3,5_triazinyl, 1,2,4-triazinyl, benzothiazolyl, benzoimidazolyl, indazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, quinoxalinyl, phthalazinyl , Cinnolinyl or quinazolinyl.)

R ¹ is halogen, CLC ,. Alkyl, C, -C ₅ alkoxycarbonyl, NO 2, CN, is one NU'IT or a N = CT ⁷ T ^8,

 n is an integer of 0 or 1;

W is halogen,, ~. ! . Alkyl, C substituted with R ^a, -C ₄ alkyl, Arukeniru of _{C 2 ~C 6, C 2 ~C} 6 alkynyl, haloalkyl, C ₂ -C _fi c Roarukeniru, C ₂ -C _B eight Roarukiniru, C ₃ -C ₆ halocycloalkyl, C, -C ₃ alkyl are optionally also optionally C. 3 to be substituted ₍₆ cycloalkyl, C ^ CB alkoxy, C2～ ₍₆ Arukeniruokishi, C ₂ -C ₆ Arukiniruo Kiss, C

Haroarukoki Shi, C2~C ₆ haloalkenyl O carboxymethyl, C ₂ -C ₆ haloalkynyl O carboxymethyl, C! C alkyl sulphates enyl, C i C alkylsulfide El, Ci C alkylsulfinyl Honiru, C2~C ₆ Arukenirusu Rufue alkenyl, c ₂ to c _fi § Luque Nils sulfinyl, Ji ;; ~ Ji ^ alkenylsulfonyl, C ₂ to CB alkyl Nils Le Hue sulfonyl, alkynylsulfinyl of C2~Ce, C ₂ ~C ₆ alkynylsulfonyl, Ji ! ~ Haroaruki Rusurufueniru, c, to c ₄ haloalkylsulfinyl, c] to c ₄ Haroarukirusu Ruhoniru, C2～Ce halo alkenyl Le Hue alkenyl, C ₂ -C ₆ halo alkenyl Le Finiru, C ₂ -C ₆ haloalkenyl sulfonyl, C2~C ₆ haloalkylene Nils Ruff Eniru, C2~C ₆ halo alkynylsulfinyl, C ₂ ~ (:? ₆ halo ^{_{alkynylsulfonyl, N0 2, CN, -NITU 2}} , phenoxy, OH, naphthyl, C2~C Arco Alkoxycarbonyl, C ₂ ~ (: 4 alkoxyalkyl, C ₂ ~ (: 4 alkylcarbonyl, C. 2 to (: 5 alkylcarbonyl O alkoxy, C ₂ -C 5 haloalkylcarbonyl O alkoxy,

Benzyl optionally substituted with X, phenyl optionally substituted with X, pyridyl optionally substituted with X, phenyl optionally substituted with X and —N = CT ⁷ T ⁸ A 5- to 8-membered ring formed by 1 to 4 substituents arbitrarily selected from or alkylene bonded at adjacent substitution positions,

Y is halogen, ji, ~. ,. Alkyl, C. Ce haloalkyl, alkoxy, C ₂ ~ (: ₆ Arukeniruokishi, C ₂ -C ₆ Arukiniruokishi, Ci～C ₄ Haroa alkoxy, C ₂ -C _fi haloalkenyl O carboxymethyl, C ₂ -C ! _B haloalkynyl O carboxymethyl, C, -C ₄ alkyl sulphates enyl, C alkylsulfinyl, - (: ₄ alkylene Rusuruhoniru, C ₂ ~ (: 6 § Luque Nils Ruff enyl, C2～Cs § Luque Nils sulfinyl, C ₂ ~ (: ₆ alkenylsulfonyl, c ₂ to c ₆ alkyl Nils Ruff enyl, c _{2-c 6} alkynylsulfinyl, C ₂ -C ₆ alkynylsulfonyl, (^ - (- ₄ Haroaru Kirusurufueniru, C, -C ₄ haloalkyl sulfinyl, (:, ~ Ji haloalkyl sulfonyl, C2～ (: 6 halo alkenyl Le Hue alkenyl, C ₂ -C ₆ eight Roarukenirusu Rufieru, c ₂ to c ₆ eight b alkenylsulfonyl, c ₂ to c ₆ haloalkylene Nils Le phenyl, c ₂ to c ₆ halo alkynylsulfinyl, C ₂ -C _B haloalkylene Nils Le ^{Honiru, N02, CN, -NU L U} 2, 〇_H, C ₂ -C ₇ alkoxycarbonyl, C ₂

-C ₄ alkoxyalkyl, C ₂ -C ₅ alkylcarbonyloxy, C _2- (: 5 halogenalkylcarbonyloxy, C ₃ -C ₇ dialkylaminocarbonylcarbonyl, phenyl optionally substituted with X, and — N = CT ⁷ T ⁸ (where T ⁷ and T ⁸ are each independently H, phenyl, benzyl or C i Cs alkyl, or 5 to ⁷ together with the carbon atom to which T ⁷ and T ⁸ are bonded) A 5- to 8-membered ring formed by 1 to 4 substituents arbitrarily selected from or alkylene bonded at adjacent substituent positions;

G is halogen, (^ ~ (: ₆ alkyl, (^ ~ (:! ₄ haloalkyl, (^ ~ (^ alkoxy, C t~C ₄ haloalkoxy, C ~C ₄ alkyl sulphates enyl, (^ ~ (^ Al Kirusurufiniru, C i~C ₄ alkylsulfonyl, C, ~C ₄ eight-neck Arukirusurufu Eniru, C! ~C ₄ haloalkylsulfinyl, C, ~C ₄ haloalkylsulfonyl, C ₂ -C ₄ alkenyl, C ₂ -C ₄ eight Roarukeniru, C ₂ -C ₄ Arukeniruokishi, C

2 to C ₄ haloalkenyl O carboxymethyl, C2~C 4 alkenyl Le Hue alkenyl, C ₂ -C ₄ Al Ke Nils sulfinyl, C ₂ ~ (: ₄ alkenylsulfonyl, c ₂ ~ c ₄ haloalkenyl Surufueniru, C ₂ ~ C ₄ halo alkenylsulfinyl, c ₂ to c ₄ eight Roarukeniru sulfonyl, c ₂ to c ₄ alkynyl, c ₂ to c ₄ haloalkynyl, c ₂ to c ₄ Arukini Ruokishi, C2~C ₄ haloalkynyl O carboxymethyl, c ₂ ~ c ₄ alkyl Nils Le Hue alkenyl, C ₂ -C ₄ alkynylsulfinyl, C ₂ ~ (: ₄ alkynylsulfonyl, c ₂ to c ₄ Bruno, Russia alkyl Nils Le Hue sulfonyl, Rei_2～ (: 4 halo alkynylsulfinyl, C ₂ -C ₄ C b alkynylsulfonyl, 'N_〇 _2, CN, formyl, C ₂ -C ₆ alkoxycarbonyl two Le, C2~ (: 4 alkylcarbonyl, C ₂ ~ (: 6 haloalkylcarbonyl, C ₂ -C ₆ Alkyl carboni 1 to 4 substituents arbitrarily selected from roux and one NITU ² ,

Τ ¹ is Ci C ^ alkyl, C ₂ -C ₆ alkenyl, Ci Cs haloalkyl, C ₂ -C ₅ alkoxyalkyl, C ₃ -C ₆ halocycloalkyl, Ci substituted with ^Ra

-C ₄ alkyl, C, -C 3 which may C. 3 to alkyl in substituted (6 cycloalkyl Le, C ₃ -C ₆ cycloalkyl substituted with R ^a, R ^a and C, -C ₄ alkyl in replacement is cyclopropyl, Rc and halogen substituted C ₃ -C ₄ cycloalkyl Le, R ^d and C ~ (: substituted at the _4-alkyl cyclopropyl, C ₂ -C ₄ substituted with R ^a alkenyl, Ci～C ₁₂ alkoxy, C i C haloalkoxy, C ₂ -C ₅ Arukeniruokishi, C i~C ₃ alkyl substituted C ₃ -C ₆ optionally Shikuroa alkoxy, Benjiruokishi, C2～C ₅ Alkoxycarbonyl, — NU'U ² , phenylamino, phenyl optionally substituted with Z, phenoxy optionally substituted with Z, phenylthio optionally substituted with Z, substituted with Z May be substituted with naphthyl or Z 5- or 6-membered heterocyclic group (provided that these heterocyclic groups are phenyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1 , 2,4-oxaziaziryl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2 , 3, 4-tetrazolyl, pyridyl, It is selected from pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl and 1,2,4-triazinyl. )

T ² and T ³ are each independently, OH, phenyl, C, -C ₆ alkyl, C, -C ₆ § alkoxy or C, a -C ₄ alkyl sulphates enyl,

T ^4, the T ⁵ and T ^beta, each independently, Η, (:, ~ ( :! 6 alkyl, C Ce alkenyl, C, -C ₃ optionally C ₃ be alkyl substituted -C ₆ cycloalkyl Or benzyl, or two of T ⁴ , Τ ⁵ and Τ ⁶ may each contain an oxygen, nitrogen or sulfur atom together with the nitrogen atom to which they are attached 5 To form an 8-membered ring group,

X and Ζ are each independently halogen, C CA alkyl,

Roaru Kill, Ci Ca alkoxy, C, -C ₄ haloalkoxy, (^ - (- ₄ Arukirusurufu Eniru, C, -C ₄ alkylsulfinyl, C i Ca alkylsulfonyl, C ₂ -C

₅ § Luque Nils Le Hue alkenyl, C ₂ -C ₅ alkenylsulfinyl, C 2 to C ₅ alkenyl Rusuruhoniru, C i C haloalkylsulfenyl phenylalanine, C i C eight Roarukirusuru Finiru, C i~C ₄ haloalkylsulfonyl, N0 _2, CN, CH_〇, ^〇_H, - N υ ι υ phenyl, to 1 chosen arbitrary among phenoxy and c ₂ to c ₅ alkoxycarbonyl is 5 substituents,

T ⁷ and T ⁸ are each independently H, phenyl, benzyl or C! -6 alkyl, or form a 5- to 8-membered ring with the carbon atom to which T ⁷ and T ⁸ are bonded. Well,

U ¹ and U ² are each independently H, C! Ce alkyl, C ₂ -C ₅ alkylcarbonyl, C _2- (: ₅ alkoxycarbonyl, phenyl or benzyl, or U ¹ and U ² May form a 5- to 8-membered ring with the carbon atom to which it is attached,

R ^a is phenyl optionally substituted with one or more selected from halogen and C alkyl;

R ^b is substituted with one or more selected from halogen and C i Ca alkyl.

Rc is phenyl optionally substituted by one or more selected from halogen and C alkoxy, R ^ri is an acrylonitrile compound represented by the formula: C _2- (: ₄ alkenyl optionally substituted with halogen).

 2. The acrylonitrile compound according to claim 1, wherein Q is thiazolyl substituted with R.

 3. The acrylonitrile compound according to claim 1, wherein Q is birazolyl substituted with R.

 4. The acrylonitrile compound according to claim 1, wherein R is pyrimidinyl or birazinyl optionally substituted with G.

 5. An agricultural chemical comprising one or more of the acrylonitrile compounds according to claims 1 to 4 as an active ingredient.