KR100502516B1 - Harmful biocontrol agents with ethylene derivatives and di derivatives - Google Patents

Abstract

Ethylene Derivatives of Formula (I) below:

In which Q is an unsubstituted or substituted phenyl group or heterocyclic group, in particular 4-thiazolyl, 1- or 3-pyrazolyl, 1,3-oxazol-4-yl, phenyl or pyridyl group; E is a substituent such as a cyano group; A is a substituent such as 4-pyrazolyl group or thiazolyl group; And B is a substituent such as an alkylcarbonyl group.

Agrochemicals and aquatic adhesion inhibitors containing at least one of the foregoing ethylene derivatives are provided.

Description

Ethylene Derivatives and Harmful Control Agents Containing the Derivatives

The present invention relates to a novel ethylene derivative, and also relates to agrochemicals and aquatic adhesion inhibitors containing the derivative as an active ingredient. Pesticides as used in the present invention include insecticides, acaricides, nematicides, herbicides and fungicides, and particularly include pesticides in agriculture, horticulture, livestock and sanitation. Anti-Aquatic Anti-Adhesion Agents are used to protect harmful aquatic organisms such as shellfish and algae from marine equipment such as fishing nets, bottoms, buoys, marine structures, circulating water systems in thermal and nuclear power plants, inflow channels for heat exchanger cooling water in the chemical industry, It is a chemical to prevent attachment to underwater constructs and water reservoirs.

As for an acrylonitrile derivative, Japanese Patent Laid-Open No. 53-92769 discloses 2'-chloro-3-hydroxy-2- (4-phenyl-2-thiazolyl) -cinnamoyl nitrile as an insecticide, International Publication No. WO-95 / 29591 discloses its use as an underwater adhesion inhibitor. Japanese Patent Laid-Open No. 60-11452 discloses the use of 2- (4-chlorophenyl) -3- (3-pyridyl) -3-oxopropionitrile as a herbicide, and Japanese Patent Laid-Open No. 60 -11401 discloses its use as a fungicide.

With the long-term use of pesticides and fungicides, some pests have recently become resistant to drugs, making them difficult to eradicate as conventional pesticides and fungicides. Moreover, some pesticides are highly toxic and do not degrade and tend to survive for a long time, destroying the ecosystem. Therefore, the development of new pesticides and fungicides with low toxicity and low residual rate is always expected.

On the other hand, to prevent adhesion and growth of marine and freshwater aquatic organisms, antifouling coatings containing organic tin compounds such as bis (tributyltin) or copper compounds such as copper sulfate and cuprous oxide are used. The organotin compounds, however, have the effect of preventing the attachment of aquatic organisms, but are highly toxic, especially in the body of fish and shellfish. Therefore, the use of these compounds is currently under legal control as it promotes environmental pollution. Copper compounds are widely used for antifouling coatings on inlet channels and bottoms, but like tin compounds, copper compounds contain heavy metal copper. Therefore, the use of a copper compound will cause environmental pollution in the future, and therefore, an aquatic biofouling agent containing such a copper compound is not preferable. Considering the above situation, there is a demand for aquatic organisms that have little effect on the ecosystem and hardly cause secondary pollution.

In order to solve the above problems, the present inventors have made intensive studies to develop pesticides and aquatic organisms that have excellent pesticide activity and have little effect on non-target organisms such as mammals, fish and useful insects. As a result, it was found that the compounds mentioned below are extremely safe, have excellent pesticide activity, and have excellent anti-aquatic adhesion. Based on these facts, the present inventors completed the present invention.

That is, the present invention provides the following [1] to [25].

[1] an ethylene derivative of formula (I)

[Wherein Q is a phenyl group optionally substituted by G, a naphthyl group optionally substituted by G, or a heterocyclic group optionally substituted by R (the heterocyclic group being thienyl, furyl, pyrrolyl, oxazolyl, iso Oxazolyl, thiazolyl, isothiazolyl, pyrazolyl, 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, pyridyl, pyri Midinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,4,5-tetrazinyl, pyrazolinyl, imidazolinyl, oxazoli Nil, isoxoxazolinyl, thiazolinyl, imidazolinone, imidazolidinedione, 3 (2H) -pyridazinone, benzothiazolyl, benzimidazolyl, indazolyl, benzoxazolyl, quinolyl, Isoquinolyl, quinoxalinyl, phthalazinyl, cinnaolinyl or quinazolinyl groups) It represents;

A is a phenyl group optionally substituted by W, a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y (the heterocyclic group being thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl , Isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadia Zolyl, 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, pyrazolinyl, imidazolinyl, oxazolinyl, isoxoxazolinyl, thiazolinyl, 3 (2H)- Pyridazinone, benzothiazolyl, benzimidazolyl, indazolyl, benzoxazolyl, quinolyl, isoquinolyl, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl group;

Provided that (a) when Q is a thienyl group optionally substituted by R, a furyl group optionally substituted by R, a quinolyl group optionally substituted by R or an isoquinolyl group optionally substituted by R, W is A phenyl group optionally substituted by, a naphthyl group optionally substituted by W or a heterocyclic group optionally substituted by Y (the heterocyclic group being pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, already Dazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-tria Zolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-tria Genyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, 3 (2H) -pyridazinone, benzothiazolyl, benzimidazolyl , Indazolyl, benzoxazolyl, quinone Salicylate carbonyl, phthalazine possess sour fun carbonyl or quinazolinyl group) and;

(b) when Q is a 2-thiazolyl group optionally substituted by R, A is a naphthyl group optionally substituted by W or a heterocyclic group optionally substituted by Y (the heterocyclic group being thienyl, furyl, pyrrolyl, Oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, 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, Pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxoxazolinyl, Thiazolinyl, 3 (2H) -pyridazinone, benzothiazolyl, benzimidazolyl, indazolyl, benzoxazolyl, quinolyl, isoquinolyl, quinoxalinyl, phthalazinyl, cinnaolinyl or quinazoli Niyl group);

(c) when Q is a pyridyl group optionally substituted by R, A is a heterocyclic group optionally substituted by Y (the heterocyclic group being pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl , 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, pyrazinyl, 1,3,5-triazinyl, 1,2, 4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxoxazolinyl, thiazolinyl, 3 (2H) -pyridazinone, benzothiazolyl, benzimidazolyl, indazolyl, benzoxa Zolyl, quinoxalinyl, phthalazinyl, cynolinyl or quinazolinyl group;

(d) when Q is an isothiazolyl group optionally substituted by R, a 1,2,3-triazolyl group optionally substituted by R or a benzoxazolyl group optionally substituted by R, then A is optionally selected by W A substituted naphthyl group or a heterocyclic group optionally substituted by Y (the heterocyclic group is thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, 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, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1 , 2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, 3 (2H) -pyridazinone, benzothiazolyl, benzimidazolyl, indazolyl , Benzoxazolyl, quinolyl, isoquinolyl, quinoxali , Phthalazine possess sour fun carbonyl or quinazolinyl group) and;

(e) when Q is a 1,2,4-triazolyl group optionally substituted by R, A is a heterocyclic group optionally substituted by Y (the heterocyclic group is thienyl, furyl, pyrrolyl, oxazolyl, isoxa Zolyl, thiazolyl, isothiazolyl, pyrazolyl, 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, pyra Genyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxoxazolinyl, thiazolinyl, 3 (2H) Pyridazinone, benzothiazolyl, benzimidazolyl, indazolyl, benzoxazolyl, quinolyl, isoquinolyl, quinoxalinyl, phthalazinyl, cinnaolinyl or quinazolinyl group;

(f) when Q is a benzothiazolyl group optionally substituted by R, A is a naphthyl group optionally substituted by W or a heterocyclic group optionally substituted by Y (the heterocyclic group being furyl, pyrrolyl, oxazolyl, iso Oxazolyl, thiazolyl, isothiazolyl, pyrazolyl, 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, pyridyl, pyri Midinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxoxazolinyl, thiazolinyl, 3 (2H) -pyridazinone, benzothiazolyl, benzimidazolyl, indazolyl, benzoxazolyl, quinolyl, isoquinolyl, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl group) ;

(g) when Q is a benzimidazolyl group optionally substituted by R, A is a naphthyl group optionally substituted by W or a heterocyclic group optionally substituted by Y (the heterocyclic group is pyrrolyl, oxazolyl, isoxa Zolyl, thiazolyl, isothiazolyl, pyrazolyl, 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, pyrazinyl, 1, 3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isooxazolinyl, thiazolinyl, 3 (2H) -pyridazinone, benzothiazolyl Benzimidazolyl, indazolyl, benzoxazolyl, quinolyl, isoquinolyl, quinoxalinyl, phthalazinyl, cinnaolinyl or quinazolinyl group;

(h) when Q is a phenyl group optionally substituted by G, A is a heterocyclic group optionally substituted by Y (the heterocyclic group is a pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, 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, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1 , 2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, 3 (2H) -pyridazinone, benzothiazolyl, benzimidazolyl, indazolyl Benzoxazolyl, quinoxalinyl, phthalazinyl, cynolinyl or quinazolinyl group;

(i) when Q is a naphthyl group optionally substituted by G, A is a heterocyclic group optionally substituted by Y (the heterocyclic group is thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl , Pyrazolyl, 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, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl , 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxoxazolinyl, thiazolinyl, 3 (2H) -pyridazinone, Benzothiazolyl, benzimidazolyl, indazolyl, benzoxazolyl, quinolyl, isoquinolyl, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl group;

B is H, a C ₁ -C ₄ alkyl group, a C ₁ -C ₄ haloalkyl group, a C ₂ -C ₄ alkoxyalkyl group, CH ₃ SCH ₂ , CH ₃ OC ₂ H ₄ OCH ₂ , a halogen or a C ₁ -C ₄ alkyl group the optionally substituted by a substituted phenyl C ₁ -C ₄ alkyl group, a halogen or a C ₁ -C a C ₁ -C substituted by an optionally substituted benzoyl group by the _{4 4} alkyl group, a tetrahydropyranyl group, (CH _{3) 3} Si , C ₁ -C ₄ alkylsulfonyl, halogen or C ₁ optionally substituted phenylsulfonyl group, -SO by -C ₄ alkyl ₂ CF _3, C ₁ -C ₄ mono-alkyl aminosulfonyl group, C ₂ -C ₈ D. Alkylaminosulfonyl group, phenylaminosulfonyl group, C ₂ -C ₅ monoalkylaminothiocarbonyl group, C ₃ -C ₉ dialkylaminothiocarbonyl group, C ₂ -C ₅ cyanoalkyl group, C ₃ -C ₉ alkoxycarbonylalkyl group , -C (= 0) T ¹ , -P (= 0) T ² T ³ , -P (= S) T ² T ³ , an alkali metal atom, an alkaline earth metal atom or NHT ⁴ T ⁵ T ⁶ ;

Provided that when Q is a 2-thiazolyl group or 2-benzothiazolyl group, then B is a C ₁ -C ₄ alkyl group, a C ₁ -C ₄ haloalkyl group, a C ₂ -C ₄ alkoxyalkyl group, CH ₃ SCH ₂ , CH ₃ OC ₂ H ₄ OCH _2, a halogen or a C ₁ -C by a C ₁ -C ₄ alkyl, halogen or C ₁ -C ₄ alkyl group substituted by a phenyl group optionally substituted by _4-alkyl group substituted by a benzoyl group optionally substituted C ₁ - C ₄ alkyl group, tetrahydropyranyl group, (CH ₃ ) ₃ Si, C ₁ -C ₄ alkylsulfonyl group, phenylsulfonyl group optionally substituted by halogen or C ₁ -C ₄ alkyl group, -SO ₂ CF ₃ , C ₁ -C ₄ monoalkylaminosulfonyl group, C ₂ -C ₈ dialkylaminosulfonyl group, phenylaminosulfonyl group, C ₂ -C ₅ monoalkylaminothiocarbonyl group, C ₃ -C ₉ dialkylaminothiocarbonyl group, C _2- A C ₅ cyanoalkyl group, a C ₃ -C ₉ alkoxycarbonylalkyl group, -C (= 0) T ¹ , -P (= 0) T ² T ³ , or -P (= S) T ² T ³ ;

E is a heterocyclic group optionally substituted by a C ₁ -C ₄ alkyl group or a C ₁ -C ₄ haloalkyl group (the heterocyclic group being 2-oxazolyl, 2-thiazolyl, 2-imidazolyl, 1,2,4- Triazol-3-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-thiadiazol-3-yl, 1,3,4-oxadiazol-2-yl, 5 -Tetrazolyl, 2-oxazolinyl or 1,2,4,5-tetrazin-3-yl group) or phenylethy optionally substituted by halogen, C ₂ -C ₄ alkynyl group, Z Nyl group, C ₁ -C ₄ haloalkyl group, CN, isonitrile group, NO ₂ , N ₃ , CHO, C ₂ -C ₅ alkylcarbonyl group, C ₂ -C ₅ alkoxycarbonyl group, C ₃ -C ₅ alkenyloxycarbonyl group, C ₂ -C ₄ alkylaminocarbonyl group, C ₃ -C ₉ dialkylaminocarbonyl group, benzoyl group optionally substituted by Z, aminothiocarbonyl group, C ₁ -C ₄ alkylsulphenyl group, C ₁ -C ₄ alkylsulfinyl group, C ₁ -C ₄ alkylsulfonyl group, phenylsulphenyl group optionally substituted by Z, phenyl optionally substituted by Z A sulfinyl group, a phenylsulfonyl group optionally substituted with Z, -P (= 0) T ² T ³ , or -P (= S) T ² T ³ ;

G is a C ₁ -C ₄ alkyl group substituted with a halogen atom, a C ₁ -C ₁₀ alkyl group, a C ₂ -C ₄ cyanoalkyl group, a halogen or a phenyl group optionally substituted by a C ₁ -C ₄ alkyl group, C ₂ -C ₆ Alkenyl group, C ₂ -C ₆ alkynyl group, C ₁ -C ₆ haloalkyl group, C ₂ -C ₆ haloalkenyl group, C ₂ -C ₆ haloalkynyl group, C ₃ -C ₆ halocycloalkyl group, C ₁ -C C ₃ -C ₆ cycloalkyl group, C ₁ -C ₁₀ alkoxy group, C ₂ -C ₆ alkenyloxy group, C ₂ -C ₆ alkynyloxy group, C ₁ -C ₄ haloalkoxy group, optionally substituted by ₃ alkyl groups, halo C ₂ -C ₆ alkenyloxy group, a halo-C ₂ -C ₆ alkynyloxy group, C ₁ -C ₄ alkylsulfonyl group, C ₁ -C ₄ alkylsulfinyl group, C ₁ -C ₄ alkylsulfonyl, C ₂ - C ₆ alkenyl nilsul phenyl group, C ₂ -C ₆ alkenyl, sulfinyl group, C ₂ -C ₆ alkenyl sulfonyl group, C ₂ -C ₆ alkynyl nilsul phenyl group, C ₂ -C ₆ alkynyl, alkoxy group, C ₂ -C ₆ alkynyl sulfonyl group, C ₁ -C ₄ haloalkylsulfinyl group, C ₁ -C ₄ haloalkylsulfinyl group, C ₁ -C ₄ haloalkylsulfonyl group, C ₂ -C ₆ Roal Kane nilsul phenyl C ₂ -C ₆ haloalkenyl alkylsulfinyl group, C ₂ -C ₆ haloalkenyl sulfonyl group, C ₂ -C ₆ haloalkynyl nilsul phenyl group, C ₂ -C ₆ haloalkynyl sulfinyl group, C ₂ - C ₆ haloalkynylsulfonyl group, methoxy group substituted with CHO, NO ₂ , CN, -NU ¹ U ² , OH, naphthyl group, halogen or phenyl group optionally substituted by C ₁ -C ₄ alkyl group, C ₂ -C ₇ alkoxycarbonyl group, C ₂ -C ₄ alkoxyalkyl group, C ₂ -C ₄ alkylcarbonyl group, C ₂ -C ₄ haloalkylcarbonyl group, C ₂ -C ₅ alkylcarbonyloxy group, C ₂ -C ₅ haloalkylcarbonylocta A period, a C ₃ -C ₇ dialkylaminocarbonyloxy group, a phenyl group optionally substituted by Z, a phenoxy group optionally substituted by Z, a benzoyl group optionally substituted by Z, a pyridyl group optionally substituted by Z, A pyridyloxy group optionally substituted by Z, a thienyl group optionally substituted by Z, a methylenedioxy group bonded to an adjacent substituent, and a substituent at an adjacent substituent The halo-methylene-dioxide group, and -N = CT ⁷ T ⁸ (wherein T ⁷ and T ⁸ are H, or represent a group or a phenyl group, a benzyl group or a C ₁ -C ₆ alkyl group independently, or T ⁷ and T ⁸ are they A substituent optionally selected from 5 to 6, 7 or 8 membered rings together with the carbon atoms to be bonded, provided that the substituents are the same or different when two or more substituents are used, and the number of substituents G is 1, 2, 3 or 4; Or G is an alkylene group bonded to an adjacent substitution position to form a 5, 6, 7 or 8 membered ring;

R is a halogen atom, C ₁ -C ₁₀ alkyl, halogen or C ₁ -C ₄ alkyl group substituted by a by a phenyl group optionally substituted with C ₁ -C ₄ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl group, C ₁ -C ₆ haloalkyl group, C ₂ -C ₆ haloalkenyl group, C ₂ -C ₆ haloalkynyl group, C ₃ -C ₆ halocycloalkyl group, C ₁ -C a alkyl optionally substituted by _three C ₃ -C ₆ cycloalkyl group, C ₁ -C ₆ alkoxy group, C ₂ -C ₆ alkenyloxy group, C ₂ -C ₆ alkynyloxy group, C ₁ -C ₄ haloalkoxy group, C ₂ -C ₆ haloalkenyloxy group , C ₂ -C ₆ alkynyloxy group halo, C ₁ -C ₄ alkylsulfonyl group, C ₁ -C ₄ alkylsulfinyl group, C ₁ -C ₄ alkylsulfonyl, C ₂ -C ₆ alkenyl nilsul phenyl group, C ₂ - C ₆ alkenylsulfinyl group, C ₂ -C ₆ alkenylsulfonyl group, C ₂ -C ₆ alkynylsulphenyl group, C ₂ -C ₆ alkynylsulfinyl group, C ₂ -C ₆ alkynylsulfonyl group, C ₁ -C ₄ haloalkylsulphenyl group, C ₁ -C ₄ haloalkylsulfinyl group, C ₁ -C ₄ haloalkylsulfonyl group, C ₂ -C ₆ haloalkenylsulphenyl group, C ₂ -C ₆ haloalkenylsulfinyl group, C ₂ -C ₆ haloalkenylsulfonyl group, C ₂ -C ₆ haloalkynylsulphenyl group, C ₂ -C ₆ haloalkynylsulfinyl group, C ₂ -C ₆ haloalkynyl Sulfonyl group, NO ₂ , CN, -NU ¹ U ² , phenoxy group, OH, naphthyl group, C ₂ -C ₇ alkoxycarbonyl group, C ₂ -C ₄ alkoxyalkyl group, C ₂ -C ₄ alkylcarbonyl group, C ₂ -C ₅ alkylcarbonyloxy group, C ₂ -C ₅ haloalkylcarbonyloxy group, benzoyl group optionally substituted by X, phenyl group optionally substituted by X, pyridyl group optionally substituted by X, optionally substituted by X A thienyl group and a substituent optionally selected from -N = CT ⁷ T ⁸ , provided that when the two or more substituents are used, the substituents are the same or different, and the number of substituents R is 1, 2, 3 or 4 ; Or R is an alkylene group bonded to an adjacent substitution position to form a 5, 6, 7 or 8 membered ring;

Y is a halogen atom, C ₁ -C ₁₀ alkyl group, C ₁ -C ₆ haloalkyl group, C ₁ -C ₆ alkoxy group, C ₂ -C ₆ alkenyloxy group, C ₂ -C ₆ alkynyloxy group, C ₁ -C ₄ haloalkoxy group, C ₂ -C ₆ alkenyloxy group halo, C ₂ -C ₆ alkynyloxy group halo, C ₁ -C ₄ alkylsulfonyl group, C ₁ -C ₄ alkylsulfinyl group, C ₁ -C ₄ alkylsulfonyl group, a C ₂ -C ₆ alkenyl nilsul phenyl group, C ₂ -C ₆ alkenyl, sulfinyl group, C ₂ -C ₆ alkenyl sulfonyl group, C ₂ -C ₆ alkynyl nilsul phenyl group, C ₂ -C ₆ alkynyl, a sulfinyl group, C ₂ -C ₆ alkynylsulfonyl group, C ₁ -C ₄ haloalkylsulphenyl group, C ₁ -C ₄ haloalkylsulfinyl group, C ₁ -C ₄ haloalkylsulfonyl group, C ₂ -C ₆ haloalkenylsulphenyl group, C ₂ -C ₆ haloalkenylsulfinyl group, C ₂ -C ₆ haloalkenylsulfonyl group, C ₂ -C ₆ haloalkynylsulphenyl group, C ₂ -C ₆ haloalkynylsulfinyl group, C ₂ -C ₆ haloalky Nylsulfonyl group, NO ₂ , CN, -NU ¹ U ² , OH, C ₂ -C ₇ alkoxycarbonyl group, C ₂ -C ₄ alkoxyalkyl group, C ₂ -C ₅ alkylcarbonyloxy group, C ₂ -C ₅ A haloalkylcarbonyloxy group, a C ₃ -C ₇ dialkylaminocarbonyloxy group, a phenyl group optionally substituted by X, and -N = CT ⁷ T ⁸ , wherein T ⁷ and T ⁸ are each independently H or a phenyl group , A benzyl group or a C ₁ -C ₆ alkyl group, or T ⁷ and T ⁸ are substituents optionally selected from forming a 5, 6, 7 or 8 membered ring with the carbon atoms to which they are attached, provided that When two or more substituents are used, the substituents are the same or different), and the number of substituents Y is 1, 2, 3 or 4; Or Y is an alkylene group bonded to an adjacent substitution position to form a 5, 6, 7 or 8 membered ring;

W is a halogen atom, C ₁ -C ₆ alkyl group, C ₁ -C ₄ haloalkyl group, C ₁ -C ₄ alkoxy group, C ₁ -C ₄ haloalkoxy group, C ₁ -C ₄ alkylsulphenyl group, C ₁ -C ₄ alkylsulfinyl group, C ₁ -C ₄ alkylsulfonyl group, C ₁ -C ₄ haloalkylsulphenyl group, C ₁ -C ₄ haloalkylsulfinyl group, C ₁ -C ₄ haloalkylsulfonyl group, C ₂ -C ₄ alke group, C ₂ -C ₄ haloalkenyl group, C ₂ -C ₄ alkenyloxy group, C ₂ -C ₄ alkenyloxy group halo, C ₂ -C ₄ alkenyl nilsul phenyl group, C ₂ -C ₄ alkenyl, sulfinyl, C ₂ -C ₄ alkenylsulfonyl group, C ₂ -C ₄ haloalkenylsulphenyl group, C ₂ -C ₄ haloalkenylsulfinyl group, C ₂ -C ₄ haloalkenylsulfonyl group, C ₂ -C ₄ alkynyl group, C ₂ -C ₄ haloalkynyl group, C ₂ -C ₄ alkynyloxy group, C ₂ -C ₄ haloalkynyloxy group, C ₂ -C ₄ alkynylsulphenyl group, C ₂ -C ₄ alkynylsulfinyl group, C ₂ -C ₄ alkynyl sulfonyl group, C ₂ -C ₄ haloalkynyl nilsul phenyl group, C ₂ -C ₄ haloalkynyl sulfinyl group, C ₂ -C ₄ haloalkynyl sulfonyl group, NO _2, CN, formyl, C ₂ -C ₆ Koksi a carbonyl group, C ₂ -C ₆ alkylcarbonyl group, C ₂ -C ₆ haloalkyl group, C ₂ -C ₆ alkylcarbonyloxy group, and a substituent optionally selected from -NU ¹ U ^2, (only, two substituents dog Above, the substituents are the same or different), and the number of substituents W is 1, 2, 3 or 4;

T ¹ is a C ₁ -C ₂₀ alkyl group, C ₂ -C ₆ alkenyl group, C ₁ -C ₆ haloalkyl group, C ₁ -C ₄ alkoxy-C ₁ -C ₄ alkyl group, C ₃ -C ₆ halocycloalkyl group, halogen Or a C ₁ -C ₄ alkyl group substituted with a phenyl group substituted by a C ₁ -C ₄ alkyl group, a C ₃ -C ₆ cycloalkyl group optionally substituted by a C ₁ -C ₃ alkyl group, a halogen or a C ₁ -C ₄ alkyl group A cycloalkyl group substituted by a phenyl group optionally substituted by halogen, a cyclopropyl group substituted by two groups of a phenyl group and a C ₁ -C ₄ alkyl group optionally substituted by a halogen or a C ₁ -C ₄ alkyl group, a halogen or a C ₁ -C ₄ Substituted by two groups: a phenyl group optionally substituted by an alkoxy group and a C ₃ -C ₄ cycloalkyl group substituted by two groups of halogen, a C ₂ -C ₄ alkenyl group and C ₁ -C ₄ alkyl group optionally substituted by halogen C ₂ -C substituted with a phenyl group optionally substituted by a cyclopropyl group, a halogen or a C ₁ -C ₄ alkyl group A C ₃ -C ₆ cycloalkoxy group optionally substituted by a ₄ alkenyl group, a C ₁ -C ₁₂ alkoxy group, a C ₁ -C ₄ haloalkoxy group, a C ₂ -C ₅ alkenyloxy group, a C ₁ -C ₃ alkyl group, Benzyloxy group, C ₂ -C ₅ alkoxycarbonyl group, -NU ¹ U ² , phenylamino group, phenyl group optionally substituted by Z, phenoxy group optionally substituted by Z, phenylthio group optionally substituted by Z, to Z Naphthyl group optionally substituted by, or 5- or 6-membered heterocyclic group optionally substituted by Z (The heterocyclic group is thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyra Zolyl, 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, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1 , 3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl Imidazolinyl, oxazolinyl, isooxazolinyl, thiazolinyl and a 3 (2H) -pyridazinone group);

T ² and T ³ each independently represent an OH, a phenyl group, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkoxy group or a C ₁ -C ₄ alkylsulphenyl group;

T ⁴ , T ⁵ and T ⁶ are each independently a C ₃ -C ₆ cycloalkyl group or a benzyl group optionally substituted by H, a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ alkenyl group, a C ₁ -C ₃ alkyl group Or two of T ⁴ , T ⁵ and T ⁶ together with the nitrogen atom to which they are attached form a 5, 6, 7 or 8 membered ring group optionally containing an oxygen atom, a nitrogen atom and / or a sulfur atom;

X and Z independently represent a halogen atom, C ₁ -C ₄ alkyl group, C ₁ -C ₄ haloalkyl group, C ₁ -C ₄ alkoxy group, C ₁ -C ₄ haloalkoxy group, C ₁ -C ₄ alkylsulphenyl group, C ₁ -C ₄ alkylsulfinyl group, C ₁ -C ₄ alkylsulfonyl, C ₂ -C ₅ alkenyl nilsul phenyl group, C ₂ -C ₅ alkenyl, sulfinyl group, C ₂ -C ₅ alkenyl sulfonyl group, C ₁ - C ₄ haloalkylsulphenyl group, C ₁ -C ₄ haloalkylsulfinyl group, C ₁ -C ₄ haloalkylsulfonyl group, NO ₂ , CN, CHO, OH, -NU ¹ U ² , phenyl group, phenoxy group, and C ₂ A substituent optionally selected from a -C ₅ alkoxycarbonyl group, provided that the substituents are the same or different when there are two or more substituents, and the number of substituents X is 1, 2, 3, 4 or 5, respectively;

T ⁷ and T ⁸ each independently represent H, or a phenyl group, benzyl group or C ₁ -C ₆ alkyl group, or T ⁷ and T ⁸ represent a 5, 6, 7 or 8 membered ring together with the carbon atom to which they are attached Forms; And

U ¹ and U ² each independently represent H, C ₁ -C ₆ alkyl group, C ₂ -C ₅ alkylcarbonyl group, phenyl group or benzyl group, or U ¹ and U ² together with the nitrogen atom to which they are attached 5, 6 To form a 7 or 8 membered ring.

[2] The above [1], wherein Q is a phenyl group optionally substituted by G, a naphthyl group optionally substituted by G, or a heterocyclic group optionally substituted by R (the heterocyclic group being thienyl, furyl, pyrrolyl). , Oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxazozolyl, 1,3,4-thiadia Zolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridyl, pyrimidinyl, pyrazinyl , Pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,4,5-tetrazinyl, pyrazolinyl, imidazolinyl, imidazolylinone, or already Dazolidinedione group);

A is a phenyl group optionally substituted by W, a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y (the heterocyclic group being thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl , Isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadia Zolyl, 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, pyrazolinyl or imidazolinyl;

B is H, C ₁ -C ₄ alkyl group, C ₁ -C ₄ haloalkyl group, C ₂ -C ₄ alkoxyalkyl group, CH ₃ OC ₂ H ₄ OCH ₂ , C ₁ -C ₄ alkylsulfonyl group, halogen or C _1- Phenylsulfonyl group optionally substituted by C ₄ alkyl group, -SO ₂ CF ₃ , C ₂ -C ₈ dialkylaminosulfonyl group, C ₂ -C ₉ diaminothiocarbonyl group, C ₃ -C ₉ alkoxycarbonylalkyl group,- C (= 0) T ¹ , -P (= 0) T ² T ³ , -P (= S) T ² T ³ , an alkali metal atom, an alkaline earth metal atom or NHT ⁴ T ⁵ T ⁶ ; And

T ¹ is selected from a C ₁ -C ₂₀ alkyl group, a C ₂ -C ₆ alkenyl group, a C ₁ -C ₄ haloalkyl group, a C ₁ -C ₄ alkoxy-C ₁ -C ₄ alkyl group, a halogen or a C ₁ -C ₄ alkyl group A C ₁ -C ₄ alkyl group substituted with an optionally substituted phenyl group, a C ₃ -C ₆ halocycloalkyl group, a C ₃ -C ₆ cycloalkyl group optionally substituted by a C ₁ -C ₃ alkyl group, a halogen or a C ₁ -C ₄ alkyl group a cycloalkyl group substituted by a phenyl group optionally substituted with a halogen or by a C ₁ -C a cyclopropyl group, a halogen or a C ₁ -C ₄ alkoxy substituted with a phenyl group and C ₁ -C ₄ alkyl group optionally substituted by ₄ alkyl C ₃ -C ₄ cycloalkyl group optionally substituted with phenyl group and halogen, cyclopropyl group substituted with C ₂ -C ₄ alkenyl group optionally substituted by halogen and C ₁ -C ₄ alkyl group, halogen or C ₁ -C a C ₂ -C ₄ alkyl group optionally substituted by a phenyl group substituted by a ₄ alkenyl, C ₁ -C ₁₂ alkoxy group, C ₁ -C ₄ haloalkoxy, , C ₂ -C ₅ alkenyloxy group, C ₁ -C ₃ alkyl group optionally substituted with by _three C -C ₆ cycloalkoxy group, a benzyloxy group, C ₂ -C ₅ alkoxycarbonyl group, a phenyl group optionally substituted by Z, A phenoxy group optionally substituted by Z, a phenylthio group, a naphthyl group, or a heterocyclic group optionally substituted by Z, said heterocyclic group being selected from thienyl, furyl, oxazolyl, thiazolyl, pyrazolyl and pyridinyl groups Ethylene derivatives.

[3] The above-mentioned [2], wherein Q is a phenyl group optionally substituted by G, a naphthyl group optionally substituted by G, or the following heterocyclic group optionally substituted by R,

The heterocyclic group,

A is a phenyl group optionally substituted by W, a naphthyl group optionally substituted by W, or the following heterocyclic group optionally substituted by Y, wherein the heterocyclic group is

Provided that (a) when Q is any of Q-1, Q-2, Q-3 or Q-4, A is a phenyl group optionally substituted by W, a naphthyl group optionally substituted by W, or Y Heterocyclic group optionally substituted by (the heterocyclic group is A-5, A-6, A-7, A-8, A-9, A-10, A-11, A-12, A-13, A-14 , A-15, A-16, A-17, A-18, A-19, A-20, A-21, A-22, A-23, A-24, A-25, A-26, A -27, A-28, A-29, A-30, A-31, A-32, A-33, A-34, A-35, A-36, A-37, A-38, A-39 , A-40, A-41, A-42, A-43, A-44, A-45, A-46, A-47, A-48, A-49, A-50, A-51, A -52, A-53, A-57, A-58, A-59, A-60, A-61, A-62, A-63, A-64, A-65, A-67, A-68 , A-69, A-70, A-71, A-72, A-73, A-74 or A-75),

(b) when Q is Q-12, A is a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y (the heterocyclic group is A-1, A-2, A-3, A- 4, A-5, A-6, A-7, A-8, A-9, A-10, A-11, A-12, A-13, A-14, A-15, A-16, A-17, A-18, A-19, A-20, A-21, A-22, A-23, A-24, A-25, A-26, A-27, A-28, A- 29, A-30, A-31, A-32, A-33, A-34, A-35, A-36, A-37, A-38, A-39, A-40, A-41, A-42, A-43, A-44, A-45, A-46, A-47, A-48, A-49, A-50, A-51, A-52, A-53, A- 54, A-55, A-56, A-57, A-58, A-59, A-60, A-61, A-62, A-63, A-64, A-65, A-67, A-68, A-69, A-70, A-71, A-72, A-73, A-74 or A-75)

(c) when Q is any of Q-52, Q-53 or Q-54, A is a heterocyclic group optionally substituted by Y (the heterocyclic group is A-5, A-6, A-7, A -8, A-9, A-10, A-11, A-12, A-13, A-14, A-15, A-16, A-17, A-18, A-19, A-20 , A-21, A-22, A-23, A-24, A-25, A-26, A-27, A-28, A-29, A-30, A-31, A-32, A -33, A-34, A-35, A-36, A-37, A-38, A-39, A-40, A-41, A-42, A-43, A-44, A-45 , A-46, A-47, A-48, A-49, A-50, A-51, A-52, A-53, A-54, A-55, A-56, A-57, A -58, A-59, A-60, A-61, A-62, A-63, A-64, A-65, A-67, A-68, A-69, A-70, A-71 , A-72, A-73, A-74 or A-75).

(d) when Q is any one of Q-23, Q-24, Q-43, Q-44, Q-45, Q-46 or Q-49, A is a naphthyl group optionally substituted by W, or Heterocyclic group optionally substituted by Y (The heterocyclic group is A-1, A-2, A-3, A-4, A-5, A-6, A-7, A-8, A-9, A -10, A-11, A-12, A-13, A-14, A-15, A-16, A-17, A-18, A-19, A-20, A-21, A-22 , A-23, A-24, A-25, A-26, A-27, A-28, A-29, A-30, A-31, A-32, A-33, A-34, A -35, A-36, A-37, A-38, A-39, A-40, A-41, A-42, A-43, A-44, A-45, A-46, A-47 , A-48, A-49, A-50, A-51, A-52, A-53, A-54, A-55, A-56, A-57, A-58, A-59, A -60, A-61, A-62, A-63, A-64, A-65, A-67, A-68, A-69, A-70, A-71, A-72, A-73 , A-74 or A-75),

(e) Q is Q-37. In the case of any one of Q-38, Q-39, Q-40, Q-41 or Q-42, A is a heterocyclic group optionally substituted by Y (The heterocyclic group is A-1, A-2, A- 3, A-4, A-5, A-6, A-7, A-8, A-9, A-10, A-11, A-12, A-13, A-14, A-15, A-16, A-17, A-18, A-19, A-20, A-21, A-22, A-23, A-24, A-25, A-26, A-27, A- 28, A-29, A-30, A-31, A-32, A-33, A-34, A-35, A-36, A-37, A-38, A-39, A-40, A-41, A-42, A-43, A-44, A-45, A-46, A-47, A-48, A-49, A-50, A-51, A-52, A- 53, A-57, A-58, A-59, A-60, A-61, A-62, A-63, A-64, A-65, A-67, A-68, A-69, A-70, A-71, A-72, A-73, A-74 or A-75),

(f) when Q is a phenyl group optionally substituted by G, A is a heterocyclic group optionally substituted by Y (the heterocyclic group is A-5, A-6, A-7, A-8, A-9, A-10, A-11, A-12, A-13, A-14, A-19, A-20, A-21, A-22, A-23, A-24, A-25, A- 26, A-27, A-28, A-29, A-30, A-31, A-32, A-33, A-34, A-35, A-36, A-37, A-38, A-39, A-40, A-41, A-42, A-43, A-44, A-45, A-46, A-47, A-48, A-49, A-50, A- 51, A-52, A-53, A-60, A-61, A-62, A-63, A-64, A-65, A-67, A-68, A-69, A-70, A-71, A-72, A-73, A-74 or A-75)

(g) when Q is a naphthyl group optionally substituted by G, A is a heterocyclic group optionally substituted by Y (the heterocyclic group is A-1, A-2, A-5, A-6, A-7 , A-8, A-9, A-10, A-11, A-12, A-13, A-14, A-15, A-16, A-17, A-18, A-19, A -20, A-21, A-22, A-23, A-24, A-25, A-26, A-27, A-28, A-29, A-30, A-31, A-32 , A-33, A-34, A-35, A-36, A-37, A-38, A-39, A-40, A-41, A-42, A-43, A-44, A -45, A-46, A-47, A-48, A-49, A-50, A-51, A-52, A-53, A-54, A-55, A-56, A-57 , A-58, A-59, A-60, A-61, A-62, A-63, A-64, A-65, A-67, A-68, A-69, A-70, A -71, A-72, A-73, A-74 or A-75)

R ¹ is a halogen atom, C ₁ -C ₁₀ alkyl group, C ₂ -C ₆ alkenyl group, C ₂ -C ₆ alkynyl group, C ₁ -C ₆ haloalkyl group, C ₁ -C ₆ alkoxy group, C ₂ -C ₆ Alkenyloxy group, NO ₂ , CN, -NU ¹ U ² , OH, C ₂ -C ₇ alkoxycarbonyl group, C ₂ -C ₄ alkoxyalkyl group, C ₂ -C ₄ alkylcarbonyl group, phenyl group optionally substituted by X, X Pyridyl group optionally substituted by, thienyl group optionally substituted by X, and -N = CT ⁷ T ⁸ , wherein T ⁷ and T ⁸ are each independently H, phenyl group, benzyl group or C ₁ -C ₆ alkyl group Or T ⁷ and T ⁸ may form a 5, 6, 7 or 8 membered ring together with the carbon atom to which they are attached; Or may form a 5, 6, 7 or 8 membered ring together with the adjacent R as an alkylene group;

Y ¹ is a halogen atom, C ₁ -C ₁₀ alkyl group, C ₁ -C ₆ haloalkyl group, C ₁ -C ₆ alkoxy group, C ₂ -C ₆ alkenyloxy group, NO ₂ , CN, -NU ¹ U ² , OH , A C ₂ -C ₇ alkoxycarbonyl group, a C ₂ -C ₄ alkoxyalkyl group, a phenyl group optionally substituted by X and -N = CT ⁷ T ⁸ , wherein T ⁷ and T ⁸ are each independently H, a phenyl group, a benzyl group or Or a C ₇ -C ₆ alkyl group, or T ⁷ and T ⁸ may form a 5, 6, 7 or 8 membered ring together with the carbon atom to which they are bonded; Or may form a 5, 6, 7 or 8 membered ring together with the adjacent Y ¹ as an alkylene group;

X is one substituent of the substituent having 1 to 4, X is a halogen atom, C ₁ -C ₄ alkyl group, C ₁ -C ₄ haloalkyl group, C ₁ -C ₄ alkoxy group, C ₁ -C ₄ haloalkoxy group, C ₁ -C ₄ alkylsulfonyl group, C ₁ -C ₄ alkylsulfinyl group, C ₁ -C ₄ alkylsulfonyl, C ₂ -C ₅ alkenyl nilsul phenyl group, C ₂ -C ₅ alkenyl, sulfinyl group, C ₂ -C ₅ alkenylsulfonyl group, C ₁ -C ₄ haloalkylsulphenyl group, C ₁ -C ₄ haloalkylsulfinyl group, C ₁ -C ₄ haloalkylsulfonyl group, NO ₂ , CN, CHO, OH, -NU ¹ U ² , Phenyl group, phenoxy group and C ₂ -C ₅ alkoxycarbonyl group, provided that the substituents may be the same or different when the number of substituents X is two or more;

Z is one substituent of the substituent having 1 to 4, and a halogen atom, C ₁ -C ₄ alkyl group, C ₁ -C ₄ haloalkyl group, C ₁ -C ₄ alkoxy group, C ₁ -C ₄ haloalkoxy group, C ₁ -C ₄ alkylsulfonyl group, C ₁ -C ₄ alkylsulfinyl group, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ alkenyl nilsul phenyl group, C ₁ -C ₄ alkenyl, sulfinyl, C ₁ -C ₄ is optionally selected from alkenylsulfonyl groups, NO ₂ , CN, -NU ¹ U ² , phenyl groups, phenoxy groups and C ₂ -C ₅ alkoxycarbonyl groups, provided that the substituents are the same when the number of substituents Z is two or more Or may be different);

m represents the number of substituents and is 0, 1, 2 or 3;

n represents the number of substituents and is 0, 1, 2, 3 or 4;

p represents the number of substituents and is 0, 1 or 2;

q represents the number of substituents and is 0 or 1;

(Wherein each substituent may be the same or different when m, n and p are each two or more integers).

[4] The ethylene derivative according to the above [2], wherein E is CN.

[5] The ethylene derivative according to the above [3], wherein E is CN.

[6] The above-mentioned [2], wherein E is a heterocyclic group optionally substituted with a C ₁ -C ₄ alkyl group or a C ₁ -C ₄ haloalkyl group (the heterocyclic group is 2-oxazolyl, 2-thiazolyl, 2 Imidazolyl, 1,2,4-triazol-3-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-thiadiazol-3-yl or 1,3, 4-oxadiazol-2-yl group), or a halogen atom, a C ₂ -C ₄ alkynyl group, a phenylethynyl group optionally substituted by Z, a C ₁ -C ₄ haloalkyl group, CN, NO ₂ , N ₃ , CHO, C ₂ -C ₅ alkylcarbonyl group, C ₂ -C ₅ alkoxycarbonyl group, C ₂ -C ₄ alkylaminocarbonyl group, C ₃ -C ₉ dialkylaminocarbonyl group, benzoyl group optionally substituted by Z, aminothio a carbonyl group, C ₁ -C ₄ alkylsulfonyl group, a C ₁ -C ₄ alkylsulfinyl group, C ₁ -C ₄ alkylsulfonyl group, a phenylsulfonyl group optionally substituted by Z, a phenyl sulfinyl group optionally substituted by Z, Z Phenylsulfonyl group optionally substituted by -P (= 0) T ² T ³ or -P (= S) T ² T ³ phosphorus ethylene derivative.

[7] The above-mentioned [3], wherein E is a heterocyclic group optionally substituted with a C ₁ -C ₄ alkyl group or a C ₁ -C ₄ haloalkyl group (the heterocyclic group is 2-oxazolyl, 2-thiazolyl, 2 Imidazolyl, 1,2,4-triazol-3-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-thiadiazol-3-yl or 1,3, 4-oxadiazol-2-yl group), or a halogen atom, a C ₂ -C ₄ alkynyl group, a phenylethynyl group optionally substituted by Z, a C ₁ -C ₄ haloalkyl group, CN, NO ₂ , N ₃ , CHO, C ₂ -C ₅ alkylcarbonyl group, C ₂ -C ₅ alkoxycarbonyl group, C ₂ -C ₄ alkylaminocarbonyl group, C ₃ -C ₉ dialkylaminocarbonyl group, benzoyl group optionally substituted by Z, aminothio a carbonyl group, C ₁ -C ₄ alkylsulfonyl group, a C ₁ -C ₄ alkylsulfinyl group, C ₁ -C ₄ alkylsulfonyl group, a phenylsulfonyl group optionally substituted by Z, a phenyl sulfinyl group optionally substituted by Z, Z Phenylsulfonyl group optionally substituted by -P (= 0) T ² T ³ or -P (= S) T ² T ³ phosphorus ethylene derivative.

[8] The above-mentioned [4], wherein Q is a phenyl group optionally substituted by G, an oxazolyl group optionally substituted by R, a thiazolyl group optionally substituted by R, a pyrazolyl group optionally substituted by R And an ethylene derivative which is a 1,2,3-triazolyl group optionally substituted by R, a pyridinyl group optionally substituted by R, or a pyrimidinyl group optionally substituted by R.

[9] The ethylene derivative according to the above [8], wherein Q is a phenyl group optionally substituted with G.

[10] The ethylene derivative according to the above [8], wherein Q is an oxazolyl group optionally substituted by R or a 1,2,3-triazolyl group optionally substituted by R.

[11] The ethylene derivative according to the above [8], wherein Q is a thiazolyl group optionally substituted with R.

[12] The ethylene derivative according to the above [8], wherein Q is a pyrazolyl group optionally substituted with R.

[13] The above-mentioned [5], wherein Q is a phenyl group optionally substituted by G, or Q-9, Q-10, Q-11, Q-12, Q-13, Q-14, Q-25 , Q-26, Q-27, Q-28, Q-29, Q-30, Q-44, Q-45, Q-46, Q-47, Q-52, Q-53, Q-54, Q Ethylene derivative which is -55, Q-56 or Q-57.

[14] The above-mentioned [7], wherein Q is a phenyl group optionally substituted with G or Q-9, Q-10, Q-11, Q-12, Q-13, Q-14, Q-25, Q-26, Q-27, Q-28, Q-29, Q-30, Q-44, Q-45, Q-46, Q-47, Q-52, Q-53, Q-54, Q- Ethylene derivative which is 55, Q-56 or Q-57.

[15] The ethylene derivative according to the above [13], wherein Q is Q-10, Q-44, Q-45, Q-46, or Q-47.

[16] The ethylene derivative according to the above [13], wherein Q is Q-12, Q-13 or Q-14.

[17] The ethylene derivative according to the above [13], wherein Q is Q-25, Q-26, Q-27, Q-28, Q-29 or Q-30.

[18] The ethylene derivative according to the above [13], wherein Q is a phenyl group optionally substituted with G.

[19] The above [2], wherein A is a phenyl group optionally substituted by W, a thiazolyl group optionally substituted by Y, a pyrazolyl group optionally substituted by Y, and a pyridinyl group optionally substituted by Y Or an ethylene derivative which is a pyrimidinyl group optionally substituted by Y.

[20] The above-mentioned [3], wherein Q is a phenyl group optionally substituted by G, a naphthyl group Q-31, Q-32, Q-33, Q-34, Q-35, Q-36, Q-37 , Q-44, Q-45, Q-46, Q-49,

ego,

A is

ego,

Y ¹ is a halogen atom, C ₁ -C ₄ alkyl group, C ₁ -C ₄ haloalkyl group, C ₁ -C ₄ alkoxy group, NO ₂ , CN or C ₂ -C ₅ alkoxycarbonyl group,

Y ² is an ethylene derivative wherein a halogen atom, a C ₁ -C ₄ alkyl group, a C ₁ -C ₆ haloalkyl group, a C ₂ -C ₄ alkoxyalkyl group, or a phenyl group optionally substituted by X.

[21] The ethylene derivative according to the above [20], wherein E is CN.

[22] The above-mentioned [20], wherein E is a heterocyclic group optionally substituted with a C ₁ -C ₄ alkyl group or a C ₁ -C ₄ haloalkyl group (the heterocyclic group is 2-oxazolyl, 2-thiazolyl, 2 Imidazolyl, 1,2,4-triazol-3-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-thiadiazol-3-yl or 1,3, 4-oxadiazol-2-yl group), or a halogen atom, a C ₂ -C ₄ alkynyl group, a phenylethynyl group optionally substituted by Z, a C ₁ -C ₄ haloalkyl group, CN, NO ₂ , N ₃ , CHO, C ₂ -C ₅ alkylcarbonyl group, C ₂ -C ₅ alkoxycarbonyl group, C ₂ -C ₄ alkylaminocarbonyl group, C ₃ -C ₉ dialkylaminocarbonyl group, benzoyl group optionally substituted by Z, aminothio a carbonyl group, C ₁ -C ₄ alkylsulfonyl group, a C ₁ -C ₄ alkylsulfinyl group, C ₁ -C ₄ alkylsulfonyl group, a phenylsulfonyl group optionally substituted by Z, a phenyl sulfinyl group optionally substituted by Z, Z Phenylsulfonyl group optionally substituted by -P (= 0) T ² T ³ or -P (= S) T ² Ethylene derivatives of T ³ .

[23] The ethylene derivative according to the above [1], selected from:

[24] A pesticide containing one or more of the ethylene derivatives described in [1] to [23] as an active ingredient.

[25] An aquatic organisms adhesion inhibitor containing at least one of the above-mentioned ethylene derivatives of [1] to [23] as an active ingredient.

[Embodiment of the Invention]

The -C (E) = C (OB)-component in the compound (I) of the present invention includes two isomers of the E and Z forms, both of which are within the scope of the present invention.

It can be seen that the compound of formula (I) of the present invention wherein the substituent B is a hydrogen atom exists as a tautomer (tautomer) as shown below.

Although compound (I) is said to exist essentially as an enol-form (1 '), they may also exist as tautomer (2) under certain conditions. The present invention includes all three of these tautomers and all mixtures thereof.

Q, A, B, E, G, R, R ¹ , Y, Y ¹ , Y ² , W, X, Z, T ¹ , T ² , T ³ , T ⁴ , T ⁵ , T ⁶ , T Preferred embodiments of ⁷ , T ⁸ , m, n, p and q are described.

The heterocyclic groups in Q, A and B represent the following meanings. That is, thienyl is thiophen-2-yl or thiophen-3-yl, furyl is furan-2-yl or furan-3-yl, pyrrolyl is pyrrole-1-yl, pyrrole-2-yl or Pyrrole-3-yl, oxazolyl is oxazol-2-yl, oxazol-3-yl, oxazol-4-yl or oxazol-5-yl, and thiazolyl is thiazol-2-yl, thia Zol-4-yl or thiazol-5-yl, imidazolyl is imidazol-1-yl, imidazol-2-yl or imidazol-4-yl and isoxazolyl isisoxazol-3- Isoisoxazol-4-yl or isoxazol-5-yl, isothiazolyl isothiazol-3-yl, isothiazol-4-yl or isothiazol-5-yl, pyrazolyl Is pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl or pyrazol-5-yl, and 1,3,4-oxadiazolyl is 1,3,4-oxadiazole- 2-yl, 1,3,4-thiadiazolyl is 1,3,4-thiadiazol-2-yl, 1,2,4-oxadiazole is 1,2,4-oxadiazole- 3- or 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazolyl is 1, 2,4-thiadiazol-3-yl or 1,2,4-thiadiazol-5-yl, 1,2,4-triazolyl is 1,2,4-triazol-1-yl, 1 , 2,4-triazol-3-yl or 1,2,4-triazol-4-yl and 1,2,3-thiadiazolyl is 1,2,3-thiadiazol-4-yl or 1,2,3-thiadiazol-5-yl, 1,2,3-triazolyl is 1,2,3-triazol-1-yl, 1,2,3-triazol-2-yl or 1,2,3-triazol-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-tetrazol-5-yl, pyridyl is pyridin-2-yl, pyridin-3-yl or pyridin-4-yl, pyrimidinyl is pyrimidine- 2-yl, pyrimidin-4-yl or pyrimidin-5-yl, pyrazinyl is pyrazin-2-yl, pyridazinyl is pyridazin-3-yl or pyridazin-4-yl, 1, 3,5-triazinyl is 1,3,5-triazin-2-yl, 1,2,4-triazinyl is 1,2,4-triazin-3-yl, 1,2,4-tri Azine-5-yl or 1,2,4-triazin-6-yl, 1,2,4,5-tetrazinyl is 1,2,4 , 5-tetrazin-3-yl, and pyrazolinyl is 3-pyrazolin-1-yl, 3-pyrazolin-3-yl, 3-pyrazolin-4-yl or 3-pyrazolin-5-yl Imidazolinyl is 1-imidazolin-3-yl, 1-imidazolin-2-yl, 1-imidazolin-4-yl or 4-imidazolin-2-yl, oxazoli Neyl is 2-oxazolin-2-yl, 2-oxazolin-4-yl or 2-oxazolin-5-yl, and isooxazolinyl is 2-isoxazolin-3-yl, 2-isooxazoline -4-yl or 2-isooxazolin-5-yl, thiazolinyl is 2-thiazolin-2-yl, 2-thiazolin-4-yl or 3-thiazolin-2-yl, and imida Zolidinone-yl is imidazolidin-2-one-1-yl, imidazolinone-yl is 2-imidazolinone-1-yl, and 3 (2H) -pyridazinone-yl is 3 (2H). ) -Pyridazinone-2-yl, 3 (2H) -pyridazinone-4-yl, 3 (2H) -pyridazinone-5-yl or 3 (2H) -pyridazinone-6-yl.

Preferred ranges of Q are the following groups.

QI: phenyl, thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxa Diazolyl, 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, 1,3,5-triazinyl, 1,2,4, 5-tetrazinyl.

QII: phenyl, thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1 , 2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridyl, pyrimidinyl.

QIII: phenyl, thienyl, oxazolyl, thiazolyl, pyrazolyl, pyridinyl, pyrimidinyl, 1,2,3-triazolyl.

QIV: phenyl.

QV: oxazolyl.

QVI: thiazolyl.

QVII: pyrazolyl.

QVIII: pyrimidinyl.

QIX: 1,2,3-triazolyl.

Preferred scope of A is the following groups.

AI: phenyl, thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxa Diazolyl, 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.

AII: phenyl, thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,3-thiadiazolyl, pyridyl , Pyrimidinyl, pyrazinyl, pyridazinyl.

AIII: phenyl, thiazolyl, pyrazolyl, pyridyl, pyrimidinyl.

AIV: thiazolyl. Pyrazolyl, pyridyl.

AV: thiazolyl.

AVI: Pyrazolyl.

AVII: pyridyl.

Preferred scope of B is the following groups.

BI: H, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₂ -C ₄ alkoxyalkyl, CH ₃ OC ₂ H ₄ OCH ₂ , C ₁ -C ₄ alkylsulfonyl, halogen or C _1- Phenylsulfonyl, optionally substituted by C ₄ alkyl, —SO ₂ CF _3, C ₂ -C ₈ dialkylaminosulfonyl, C ₃ -C ₉ dialkylaminothiocarbonyl, C ₃ -C ₉ alkoxycarbonylalkyl , -C (= O) T ¹ , -P (= O) T ² T ³ , -P (= S) T ² T ³ , alkali metal, alkaline earth metal or NHT ⁴ T ⁵ T ⁶ .

BII: H, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₂ -C ₄ alkoxyalkyl, CH ₃ OC ₂ H ₄ OCH ₂ , C ₁ -C ₄ alkylsulfonyl, -SO ₂ CF _{3 ,} -C (= O) T ¹ , alkali metal, alkaline earth metal or NHT ⁴ T ⁵ T ⁶ .

BIII: H, C ₂ -C ₄ alkoxyalkyl, C ₁ -C ₄ alkylsulfonyl, -SO ₂ CF _3, -C (═O) T ¹ , alkali metal, alkaline earth metal or NHT ⁴ T ⁵ T ⁶ .

BIV: C ₂ -C ₄ alkoxyalkyl, C ₁ -C ₄ alkylsulfonyl, -SO ₂ CF _3, -C (═O) T ¹ , alkali metal, alkaline earth metal or NHT ⁴ T ⁵ T ⁶ .

Preferred scope of E is the following groups.

EI: halogen, C ₂ -C ₄ alkynyl, phenylethynyl optionally substituted by Z, C ₁ -C ₄ haloalkyl, CN, NO ₂ , N ₃ , CHO, C ₂ -C ₅ alkylcarbonyl, C ₂ -C ₅ alkoxycarbonyl, C ₂ -C ₄ alkylaminocarbonyl, C ₃ -C ₉ dialkylaminocarbonyl, benzoyl optionally substituted by Z, aminothiocarbonyl, C ₁ -C ₄ alkylsulphenyl , C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, phenylsulphenyl optionally substituted by Z, phenylsulfinyl optionally substituted by Z, phenylsulfonyl optionally substituted by Z,- P (= O) T ² T ³ , -P (= S) T ² T ³ .

EII: halogen, C ₂ -C ₄ alkynyl, phenylethynyl optionally substituted by Z, CN, C ₂ -C ₅ alkylcarbonyl, C ₂ -C ₅ alkoxycarbonyl, C ₂ -C ₄ alkylaminocar Carbonyl, C ₃ -C ₉ dialkylaminocarbonyl, benzoyl optionally substituted by Z, C ₁ -C ₄ alkylsulphenyl, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, Z Phenylsulfonyl optionally substituted by Z, phenylsulfinyl optionally substituted by Z, phenylsulfonyl optionally substituted by Z, or -P (= 0) T ² T ³ .

EIII: CN.

Preferred scope of G is the following groups.

GI: halogen, C ₁ -C ₆ alkyl, C ₂ -C ₄ alkenyl, C ₂ -C ₄ alkynyl, C ₁ -C ₄ haloalkyl, C ₂ -C ₄ haloalkenyl, C ₂ -C ₄ halo Alkynyl, C ₃ -C ₆ cycloalkyl optionally substituted by C ₁ -C ₃ alkyl, C ₁ -C ₆ alkoxy, C ₂ -C ₄ alkenyloxy, C ₂ -C ₄ alkynyloxy, C _1- C ₄ haloalkoxy, C ₂ -C ₄ haloalkenyloxy, C ₂ -C ₄ haloalkynyloxy, C ₁ -C ₄ alkylsulphenyl, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulphur Ponyl, C ₂ -C ₄ alkenylsulphenyl, C ₂ -C ₄ alkenylsulfinyl, C ₂ -C ₄ alkenylsulfonyl, C ₂ -C ₄ alkynylsulphenyl, C ₂ -C ₄ alkynylsulfinyl, C _2- C ₄ alkynylsulfonyl, C ₁ -C ₄ haloalkylsulphenyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, C ₂ -C ₄ haloalkenylsulphenyl, C ₂ -C ₄ haloalkenylsulfinyl, C ₂ -C ₄ haloalkenylsulfonyl, C ₂ -C ₄ haloalkynylsulphenyl, C ₂ -C ₄ haloalkynylsulfinyl, C ₂ -C ₄ haloalkynylsulfonyl, NO ₂ , CN , the -NU ¹ U ^2, halogen or C ₁ -C ₄ alkyl The sun optionally substituted with phenyl substituted with methoxy, C ₂ -C ₆ alkoxycarbonyl, C ₂ -C ₄ alkoxyalkyl, C ₂ -C ₄ alkylcarbonyl, C ₂ -C ₄ haloalkyl-carbonyl, C ₂ - C ₅ alkylcarbonyloxy, C ₂ -C ₅ haloalkylcarbonyloxy, C ₃ -C ₇ dialkylaminocarbonyloxy, phenyl optionally substituted by Z, phenoxy optionally substituted by Z, by Z A substituent optionally selected from optionally substituted benzoyl, pyridyl optionally substituted by Z, and pyridyloxy optionally substituted by Z, provided that the substituents may be the same or different when there are two or more substituents, Or the number of substituents G is 1, 2, 3 or 4, or G is an alkylene group which is bonded to adjacent substitution positions to form a 5, 6, 7 or 8 ring.

GII: C ₃ -C optionally substituted by halogen, C ₁ -C ₆ alkyl, C ₂ -C ₄ alkenyl, C ₂ -C ₄ alkynyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₃ alkyl ₆ cycloalkyl, C ₁ -C ₆ alkoxy, C ₂ -C ₄ alkenyloxy, C ₂ -C ₄ alkynyloxy, C ₁ -C ₄ haloalkoxy, C ₂ -C ₄ haloalkenyloxy, C _1- C ₄ alkylsulphenyl, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₂ -C ₄ alkenylsulphenyl, C ₂ -C ₄ alkenylsulfinyl, C ₂ -C ₄ alkenylsulfonyl , C ₂ -C ₄ alkynylsulphenyl, C ₂ -C ₄ alkynylsulfinyl, C ₂ -C ₄ alkynylsulfonyl, C ₁ -C ₄ haloalkylsulphenyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, C ₂ -C ₄ haloalkenyl nilsul phenyl, C ₂ -C ₄ haloalkenyl nilsul sulfinyl, C ₂ -C ₄ haloalkenyl nilsul sulfonyl, optionally substituted by halogen or C ₁ -C ₄ alkyl Phenyl substituted with phenyl, C ₂ -C ₆ alkoxycarbonyl, C ₂ -C ₅ alkylcarbonyloxy, C ₂ -C ₅ haloalkylcarbonyloxy, phenoxy optionally substituted by Z, and A substituent optionally selected from pyridyloxy optionally substituted by Z, provided that when there are two or more substituents, the substituents may be the same or different and the number of substituents G is 1, 2 or 3.

GIII: C ₃ -C ₆ cycloalkyl optionally substituted by halogen, C ₁ -C ₆ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₃ alkyl, C ₁ -C ₆ alkoxy, C ₂ -C ₄ Alkenyloxy, C ₂ -C ₄ alkynyloxy, C ₁ -C ₄ haloalkoxy, C ₂ -C ₄ haloalkenyloxy, C ₁ -C ₄ alkylsulphenyl, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₂ -C ₄ alkenyl nilsul phenyl, C ₂ -C ₄ alkenyl nilsul sulfinyl, C ₂ -C ₄ alkenyl nilsul sulfonyl, C ₂ -C ₄ alkynyl nilsul phenyl, C ₂ -C ₄ alkynyl Nylsulfinyl, C ₂ -C ₄ alkynylsulfonyl, C ₁ -C ₄ haloalkylsulphenyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, C ₂ -C ₄ haloalkenylsul Phenyl, C ₂ -C ₄ haloalkenylsulfinyl, C ₂ -C ₄ haloalkenylsulfonyl, methoxy substituted by halogen or C ₁ -C ₄ alkyl, C ₂ -C ₆ alkoxycarbonyl , C ₂ -C ₅ alkylcarbonyloxy, phenoxy optionally substituted by Z, and pyridyloxy optionally substituted by Z The substituents provided that the substituents may be the same or different when there are two or more substituents and the number of substituents G is 1 or 2.

Preferred ranges of R are the following groups.

RI: C ₁ -C ₃ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₃ alkyl substituted with halogen, C ₁ -C ₆ alkyl, phenyl optionally substituted by halogen or C ₁ -C ₄ alkyl C ₃ -C ₆ cycloalkyl, C ₁ -C ₄ alkoxy, C ₂ -C ₄ alkenyloxy, C ₂ -C ₄ alkynyloxy, C ₁ -C ₄ haloalkoxy, C ₂ -C ₄ optionally substituted by Haloalkenyloxy, C ₂ -C ₄ haloalkynyloxy, C ₁ -C ₄ alkylsulphenyl, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₂ -C ₄ alkenylsulphenyl , C ₂ -C ₄ alkenylsulfinyl, C ₂ -C ₄ alkenylsulfonyl, C ₂ -C ₄ alkynylsulphenyl, C ₂ -C ₄ alkynylsulfinyl, C ₂ -C ₄ alkynylsulfonyl, C ₁ -C ₄ haloalkylsulphenyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, C ₂ -C ₄ haloalkenylsulphenyl, C ₂ -C ₄ haloalkenylsulfinyl, C ₂ -C ₄ haloalkenyl nilsul sulfonyl, NO _2, CN, -NU ¹ U ^2, naphthyl, C ₂ -C ₄ alkoxycarbonyl, C ₂ -C ₄ alkoxyalkyl, value by a phenyl, X is substituted by X, optionally optionally Substituents optionally selected from pyridyl and thienyl optionally substituted by X, provided that the substituents may be the same or different when there are two or more substituents, and the number of substituents R is 1, 2 or 3 or R Is an alkylene group which is bonded to an adjacent substitution position to form a 5, 6, 7 or 8 membered ring.

RII: C ₁ -C ₃ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₃ alkyl substituted with halogen, C ₁ -C ₆ alkyl, phenyl optionally substituted by halogen or C ₁ -C ₄ alkyl C ₃ -C ₆ cycloalkyl optionally substituted by, NO ₂ , CN, -NU ¹ U ² , naphthyl, C ₂ -C ₄ alkoxycarbonyl, C ₂ -C ₄ alkoxyalkyl, phenyl optionally substituted by X And a substituent optionally selected from pyridyl optionally substituted by X, provided that when there are two or more substituents, the substituents may be the same or different and the number of substituents R is 1, 2 or 3.

RIII: C ₁ -C ₃ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₃ alkyl substituted with halogen, C ₁ -C ₆ alkyl, phenyl optionally substituted by halogen or C ₁ -C ₄ alkyl C ₃ -C ₆ cycloalkyl optionally substituted by, NO ₂ , CN, -NU ¹ U ² , naphthyl, C ₂ -C ₄ alkoxycarbonyl, phenyl optionally substituted by X and pyri optionally substituted by X A substituent optionally selected from dils, provided that the substituents may be the same or different when there are two or more substituents, and the number of substituents R is 1 or 2.

The number of Rs varies depending on the kind of the heterocyclic group substituted by R. 1,3,4-oxadiazolyl, 1,2.4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,3-oxadiazolyl, 1, In the case of groups such as 2,3-thiadizolyl or 1,2,3,4-tetrazolyl, the number of R is 0 or 1, preferably 1. Thiazolyl, oxazolyl, isoxazolyl, isothiazolyl, 1,3,4-triazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,3,5-triazinyl, In the case of groups such as 1,2,4-triazinyl or 1,2,4-triazinyl, the number of R is an integer of 0 to 2, but 1 or 2 is preferable. In the case of groups such as thienyl, furyl, pyrazolyl, imidazolyl, pyrimidinyl, pyrazinyl or pyridazinyl, the number of R is an integer of 0 to 3, with an integer of 0 to 2 being preferred, and more preferred. Preferably 1 or 2. In the case of groups such as pyrrolyl, pyridyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxoxazolinyl or thiazolinyl, the number of R is an integer of 0 to 4, and an integer of 0 to 3 Preferably, it is 1 or 2 more preferably.

Preferred ranges of Y are the following groups.

YI: halogen, C ₁ -C ₆ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₂ -C ₄ alkenyloxy, C ₂ -C ₄ alkynyloxy, C ₁ -C ₄ halo Alkoxy, C ₂ -C ₄ haloalkenyloxy, C ₂ -C ₄ haloalkynyloxy, C ₁ -C ₄ alkylsulphenyl, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₂ -C ₄ alkenyl nilsul phenyl, C ₂ -C ₄ alkenyl nilsul sulfinyl, C ₂ -C ₄ alkenyl nilsul sulfonyl, C ₂ -C ₄ alkynyl nilsul phenyl, C ₂ -C ₄ alkynyl nilsul sulfinyl, C ₂ -C ₄ alkynyl Nilsulfonyl, C ₁ -C ₄ haloalkylsulphenyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, C ₂ -C ₄ haloalkenylsulphenyl, C ₂ -C ₄ haloalke Nylsulfinyl, C ₂ -C ₄ haloalkenylsulfonyl, C ₂ -C ₄ haloalkynylsulphenyl, C ₂ -C ₄ haloalkynylsulfinyl, C ₂ -C ₄ haloalkynylsulfonyl, NO ₂ , CN, -NU ¹ U ² , C ₂ -C ₄ alkoxycarbonyl, C ₂ -C ₄ alkoxyalkyl, C ₂ -C ₄ alkylcarbonyloxy, C ₂ -C ₄ haloalkylcarbonyloxy, and phenyl optionally substituted by X Randomly selected from Substituents provided that, when two or more substituents are used, the substituents may be the same or different, and the number of substituents Y is 1,2 or 3.

YII: halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylsulphenyl, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkyl On sulfonyl, C ₁ -C ₄ haloalkylsulphenyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, NO ₂ , CN, C ₂ -C ₄ alkoxycarbonyl, and X A substituent optionally selected from phenyl optionally substituted by the above, provided that the substituents may be the same or different when there are two or more substituents, and the number of substituents Y is 1, 2 or 3.

The number of Y varies depending on the kind of heterocyclic group substituted by Y. 1,3,4-oxadiazolyl, 1,2.4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,3-thiadizolyl or 1, In the case of groups such as 2,3,4-tetrazolyl, the number of Y is 0 or 1, preferably 1. Thiazolyl, oxazolyl, isoxazolyl, isothiazolyl, 1,3,4-triazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,3,5-triazinyl, In the case of groups such as 1,2,4-triazinyl or 1,2,4-triazinyl, the number of Y is an integer of 0 to 2, but 1 or 2 is preferable. In the case of groups such as thienyl, furyl, pyrazolyl, imidazolyl, pyrimidinyl, pyrazinyl or pyridazinyl, the number of Y is an integer of 0 to 3, with an integer of 0 to 2 being more preferred. Preferably 1 or 2. In the case of groups such as pyrrolyl, pyridyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxoxazolinyl or thiazolinyl, the number of Y is an integer of 0 to 4, and an integer of 0 to 3 Preferably, it is 1 or 2 more preferably.

Preferred ranges of W are the following groups.

WI: halogen, C ₁ -C ₆ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylsulphenyl, C ₁ -C ₄ alkylsulphur Finyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylsulphenyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, C ₂ -C ₄ alkenyloxy, halo C ₂ -C ₄ alkenyloxy, C ₂ -C ₄ alkenyl nilsul phenyl, C ₂ -C ₄ alkenyl nilsul sulfinyl, C ₂ -C ₄ alkenyl nilsul sulfonyl, C ₂ -C ₄ haloalkenyl nilsul phenyl, C ₂ - C ₄ haloalkenylsulfinyl, C ₂ -C ₄ haloalkenylsulfonyl, C ₂ -C ₄ alkynyloxy, C ₂ -C ₄ alkynylsulphenyl, C ₂ -C ₄ alkynylsulfinyl, C ₂ -C ₄ alkoxy Nylsulfonyl, NO ₂ , CN, C ₂ -C ₄ alkoxycarbonyl, C ₂ -C ₄ alkylcarbonyl, C ₂ -C ₄ haloalkylcarbonyl, C ₂ -C ₄ alkylcarbonyloxy and -NU ¹ U A substituent optionally selected from ² , provided that the substituents may be the same or different when there are two or more substituents, and the number of substituents W is 1, 2, 3 or 4.

WII: halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylsulphenyl, C ₁ -C ₄ alkylsulphur Finyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylsulphenyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, C ₂ -C ₄ alkenyloxy, halo C ₂ -C ₄ alkenyloxy, C ₂ -C ₄ alkenyl nilsul phenyl, C ₂ -C ₄ alkenyl nilsul sulfinyl, C ₂ -C ₄ alkenyl nilsul sulfonyl, C ₂ -C ₄ alkynyloxy, C ₂ -C ₄ alkynyl nilsul phenyl, C ₂ -C ₄ alkynyl nilsul sulfinyl, C ₂ -C ₄ alkynyl nilsul sulfonyl, and NO ₂ substituents selected arbitrarily from the CN (However, if more than one substituent, the above substituent may be the same as or different from Good ) And the number of substituents W is 1,2 or 3.

WIII: halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylsulphenyl, C ₁ -C ₄ alkylsulphur sulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylsulfinyl phenyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, NO _2, and substituents optionally selected from CN (However, when there are two or more substituents, the substituents may be the same or different), and the number of substituents W is 1 or 2.

Preferred ranges of T ¹ are the following groups.

T ¹ I: C ₁ -C ₁₈ alkyl, C ₂ -C ₆ alkenyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy-C ₁ -C ₄ alkyl, halogen or C ₁ -C ₄ alkyl optionally substituted by a substituted phenyl C ₁ -C ₄ alkyl, C ₃ -C ₆ halocycloalkyl, C ₁ -C a alkyl optionally substituted by _three C ₃ -C ₆ cycloalkyl, halogen or C ₁ -C ₄ C ₂ -C ₄ alkenyl, C ₁ -C ₁₀ alkoxy, C ₁ -C ₄ substituted with cycloalkyl, halogen or C ₁ -C ₄ optionally substituted with phenyl optionally substituted by alkyl Haloalkoxy, C ₂ -C ₅ alkenyloxy, C ₃ -C ₆ cycloalkoxy, benzyloxy, C ₂ -C ₅ alkoxycarbonyl, optionally substituted by C ₁ -C ₃ alkyl, -NU ¹ U ² , Z Phenyl optionally substituted by phenyl, phenoxy optionally substituted by Z, phenylthio optionally substituted by Z, naphthyl, and heterocyclic groups optionally substituted by Z (the heterocyclic groups being thienyl, furyl, pyrrolyl, Oxazolyl, isoxazolyl, Thiazolyl, pyrazolyl, 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, pyridyl, pyrimidinyl, pyrazinyl, pyri Dazinyl, 1,3,5-triazinyl and 1,2,4-triazinyl groups.

T ¹ II: phenyl optionally substituted by C ₁ -C ₁₈ alkyl, C ₂ -C ₆ alkenyl, C ₁ -C ₄ haloalkyl, C ₂ -C ₄ alkoxyalkyl, halogen or C ₁ -C ₄ alkyl Substituted C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl optionally substituted by C ₁ -C ₃ alkyl, halogen or cycloalkyl, halogen substituted by phenyl optionally substituted by C ₁ -C ₄ alkyl or C ₂ -C ₄ alkenyl, C ₁ -C ₁₀ alkoxy, C ₁ -C ₄ haloalkoxy, C ₂ -C ₅ alkenyloxy, C ₃ -substituted with phenyl optionally substituted by C ₁ -C ₄ alkyl C ₆ cycloalkoxy, benzyloxy, C ₂ -C ₅ alkoxycarbonyl, phenyl optionally substituted by Z, phenoxy optionally substituted by Z, phenylthio, naphthyl, and heterocyclic groups optionally substituted by Z ( The heterocyclic group is a thienyl, furyl, pyrrolyl, oxazolyl, thiazolyl, pyrazolyl and pyridinyl groups.

T ¹ III: C ₁ -C ₁₇ alkyl, C ₂ -C ₆ alkenyl, C ₁ -C ₄ haloalkyl, C ₂ -C ₄ alkoxyalkyl, C ₁ -C ₄ alkyl substituted with phenyl, C ₁ -C by ₃ alkyl, optionally substituted C ₃ -C ₆ cycloalkyl, cycloalkyl substituted by phenyl, C ₂ -C ₄ alkenyl substituted by phenyl, C ₁ -C ₈ alkoxy, C ₁ -C ₄ haloalkoxy, C ₂ -C ₅ alkenyloxy, C ₃ -C ₆ cycloalkoxy, benzyloxy, C ₂ -C ₅ alkoxycarbonyl, phenyl optionally substituted by Z, phenoxy optionally substituted by Z, phenylthio, naphthyl , Pyrazolyl optionally substituted by Z, or pyridyl group optionally substituted by Z.

Preferred ranges of T ² are the following groups.

T ² I: phenyl, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkylsulphenyl.

Preferred ranges of T ³ are the following groups.

T ³ I: phenyl, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy or C ₁ -C ₄ alkylsulphenyl.

Preferred ranges of T ⁴ are the following groups.

T ⁴ I: H, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl or benzyl.

Also preferred is that any two of T ⁴ , T ⁵ and T ⁶ together with the nitrogen atoms to which they are attached form a 5, 6 or 7 membered ring optionally having oxygen, nitrogen and / or sulfur atoms.

Preferred ranges of T ⁵ are the following groups.

T ⁵ I: H, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl or benzyl.

Also preferred is that any two of T ⁴ , T ⁵ and T ⁶ together with the nitrogen atoms to which they are attached form a 5, 6 or 7 membered ring optionally having oxygen, nitrogen and / or sulfur atoms.

Preferred ranges of T ⁶ are the following groups.

T ⁶ I: H, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl or benzyl.

Also preferred is that any two of T ⁴ , T ⁵ and T ⁶ together with the nitrogen atoms to which they are attached form a 5, 6 or 7 membered ring optionally having oxygen, nitrogen and / or sulfur atoms.

Preferred scope of X is the following groups.

XI: halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylsulphenyl, C ₁ -C ₄ alkylsulphur Finyl, C ₁ -C ₄ alkylsulfonyl, C ₂ -C ₅ alkenylsulphenyl, C ₂ -C ₅ alkenylsulfinyl, C ₂ -C ₅ alkenylsulfonyl, C ₁ -C ₄ haloalkylsulphenyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C _{4 ^{haloalkylsulfonyl, NO 2, CN, -NU 1}} U 2 and C ₂ -C ₅ substituents selected arbitrarily from an alkoxycarbonyl group (provided that when the substituents are two or more Wherein the substituents may be the same or different) and the number of substituents X is 1, 2 or 3.

XII: halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylsulphenyl, C ₁ -C ₄ alkylsulphur sulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₂ -C ₅ alkylsulfonyl-phenyl, C ₂ -C ₅ alkylsulfinyl, C ₂ -C ₅ alkylsulfonyl, C ₁ -C ₄ haloalkylsulfinyl phenyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkylsulfonyl, and NO ₂ substituents optionally selected from (in case that more than one substituent, the above substituent may be the same or different are good), and the number of the substituents X Is 1, 2 or 3.

XIII: a substituent optionally selected from halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl and C ₁ -C ₄ alkoxy group, provided that the substituents may be the same or different when there are two or more substituents And the number of substituents X is 1 or 2.

The number of X varies depending on the type of ring substituted by X. In the case of phenyl, although the number of X is an integer of 0-5, the integer of 0-3 is preferable, More preferably, it is an integer of 0-2. In the case of pyridyl, the number of X is an integer of 0 to 4, preferably 0, 1 or 2, more preferably 0 or 1. In the case of thienyl, the number of X is an integer from 0 to 3, with 0 or 1 being preferred.

Preferred ranges of Z are the following groups.

ZI: halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylsulphenyl, C ₁ -C ₄ alkylsulphur Finyl, C ₁ -C ₄ alkylsulfonyl, C ₂ -C ₆ alkenylsulphenyl, C ₂ -C ₆ alkenylsulfinyl, C ₂ -C ₆ alkenylsulfonyl, C ₁ -C ₄ haloalkylsulphenyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C _{4 ^{haloalkylsulfonyl, NO 2, CN, -NU 1}} U 2 and C ₂ -C ₅ alkoxy substituents optionally selected from carbonyl (where the substituents are two or more pieces In which case the substituents may be the same or different) and the number of substituents Z is 1, 2, 3 or 4.

ZII: halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylsulphenyl, C ₁ -C ₄ alkylsulphur Finyl, C ₁ -C ₄ alkylsulfonyl, C ₂ -C ₆ alkenylsulphenyl, C ₂ -C ₆ alkenylsulfinyl, C ₂ -C ₆ alkenylsulfonyl, C ₁ -C ₄ haloalkylsulphenyl, C ₁ -C ₄ haloalkyl sulfinyl, C ₁ -C ₄ haloalkyl substituents optionally selected from alkylsulfonyl (where, if more than one substituent, the above substituent may be the same or different are good), the number of the substituent Z is 1, 2, 3 or 4.

The number of Z varies depending on the type of ring substituted by Z. In the case of phenyl, the number of Z is an integer of 0 to 5, preferably an integer of 0 to 4, more preferably 0, 1, 2 or 3, most preferably 0, 1 or 2. In the case of naphthyl, the number of Z is an integer from 0 to 7, with 0 being preferred. When the ring substituted by Z is a heterocyclic group, the number of substituents Z also depends on the type of heterocyclic group. 1,3,4-oxadiazolyl, 1,2.4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,3-oxadiazolyl, 1, In the case of groups such as 2,3-thiadizolyl 1,2,3,4-tetrazolyl or 1,2,3,5-tetrazolyl, the number of Z is 0 or 1. Thiazolyl, oxazolyl, isoxazolyl, isothiazolyl, 1,3,4-triazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,3,5-triazinyl, In the case of groups such as 1,2,4-triazinyl or 1,2,4-triazinyl, the number of Z is an integer of 0 to 2, but 1 or 2 is preferable. In the case of groups such as thienyl, furyl, pyrazolyl, imidazolyl, pyrimidinyl, pyrazinyl or pyridazinyl, the number of Z is an integer of 0 to 3, with an integer of 0 to 2 being more preferred. Preferably 1 or 2. In the case of groups such as pyrrolyl, pyridyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxoxazolinyl or thiazolinyl, the number of Z is an integer of 0 to 4, and an integer of 0 to 2 Preferably, it is 1 or 2 more preferably.

Preferred ranges of T ⁷ are the following groups.

T ⁷ I: H, phenyl, benzyl or C ₁ -C ₄ alkyl. Also preferred is that T ⁷ and T ⁸ together with the carbon atoms to which they are attached form a five or six membered ring.

Preferred ranges of T ⁸ are the following groups.

T ⁸ I: phenyl, benzyl or C ₁ -C ₄ alkyl. Also preferred is that T ⁷ and T ⁸ together with the carbon atoms to which they are attached form a five or six membered ring.

Preferred ranges of U ¹ are the following groups.

U ¹ I: H, C ₁ -C ₄ alkyl or C ₂ -C ₆ alkylcarbonyl. Also preferred is that U ¹ and U ² together with the nitrogen atom to which they are attached form a 5, 6 or 7 membered ring.

Preferred ranges of U ² are the following groups.

U ² I: H, C ₁ -C ₄ alkyl or C ₂ -C ₆ alkylcarbonyl. Also preferred is that U ¹ and U ² together with the carbon atoms to which they are attached form a 5, 6 or 7 membered ring.

1, 2 or 3 is preferable, and m is 1 or 2 more preferably.

n is preferably 0, 1, 2 or 3, and more preferably 1 or 2.

p is preferably 1 or 2.

Preferred combinations of the above-mentioned preferred groups in the range of preferred substituents, these represent the range of preferred compounds of the present invention. Particularly preferred ranges of the above are as set forth below.

Preferred substituents QI, AI, BI, EI, GI, RI, YI, WI, T ¹ I, T ² I, T ³ I, T ⁴ I, T ⁵ I, T ⁶ I, XI, ZI, T ⁷ I, Compounds of the invention having T ⁸ I, U ¹ I and U ² I.

Preferred substituents QI, AI, BI, EIII, GI, RI, YI, WI, T ¹ I, T ² I, T ³ I, T ⁴ I, T ⁵ I, T ⁶ I, XI, ZI, T ⁷ I, Compounds of the invention having T ⁸ I, U ¹ I and U ² I.

Preferred substituents QII, AII, BI, EII, GI, RI, YI, WI, T ¹ I, T ² I, T ³ I, T ⁴ I, T ⁵ I, T ⁶ I, XI, ZI, T ⁷ I, Compounds of the invention having T ⁸ I, U ¹ I and U ² I.

Preferred substituents QII, AII, BI, EIII, GI, RI, YI, WI, T ¹ I, T ² I, T ³ I, T ⁴ I, T ⁵ I, T ⁶ I, XI, ZI, T ⁷ I, Compounds of the invention having T ⁸ I, U ¹ I and U ² I.

Preferred substituents QIII, AIII, BI, EIII, GI, RI, YI, WI, T ¹ I, T ² I, T ³ I, T ⁴ I, T ⁵ I, T ⁶ I, XI, ZI, T ⁷ I, Compounds of the invention having T ⁸ I, U ¹ I and U ² I.

Preferred substituents QIII, AIII, BII, EIII, GII, RII, YII, WII, T ¹ II, T ² I, T ³ I, T ⁴ I, T ⁵ I, T ⁶ I, XII, ZII, T ⁷ I, Compounds of the invention having T ⁸ I, U ¹ I and U ² I.

Preferred substituents QIII, AIII, BII, EIII, GIII, RIII, YII, WII, T ¹ III, T ² I, T ³ I, T ⁴ I, T ⁵ I, T ⁶ I, XIII, ZII, T ⁷ I, Compounds of the invention having T ⁸ I, U ¹ I and U ² I.

Preferred substituents QIII, AIV, BIII, EIII, GIII, RIII, YII, WII, T ¹ III, T ² I, T ³ I, T ⁴ I, T ⁵ I, T ⁶ I, XIII, ZII, T ⁷ I, Compounds of the invention having T ⁸ I, U ¹ I and U ² I.

Preferred substituents QIV, AIV, BIII, EIII, GIII, RIII, YII, WII, T ¹ III, T ² I, T ³ I, T ⁴ I, T ⁵ I, T ⁶ I, XIII, ZII, T ⁷ I, Compounds of the invention having T ⁸ I, U ¹ I and U ² I.

Preferred substituents QV, AIII, BIII, EIII, GIII, RIII, YII, WII, T ¹ III, T ² I, T ³ I, T ⁴ I, T ⁵ I, T ⁶ I, XIII, ZII, T ⁷ I, Compounds of the invention having T ⁸ I, U ¹ I and U ² I.

Preferred substituents QVI, AIII, BIII, EIII, GIII, RIII, YII, WII, T ¹ III, T ² I, T ³ I, T ⁴ I, T ⁵ I, T ⁶ I, XIII, ZII, T ⁷ I, Compounds of the invention having T ⁸ I, U ¹ I and U ² I.

Preferred substituents QVI, AIV, BIII, EIII, GIII, RIII, YII, WII, T ¹ III, T ² I, T ³ I, T ⁴ I, T ⁵ I, T ⁶ I, XIII, ZII, T ⁷ I, Compounds of the invention having T ⁸ I, U ¹ I and U ² I.

Preferred substituents QVII, AIII, BIII, EIII, GIII, RIII, YII, WII, T ¹ III, T ² I, T ³ I, T ⁴ I, T ⁵ I, T ⁶ I, XIII, ZII, T ⁷ I, Compounds of the invention having T ⁸ I, U ¹ I and U ² I.

Preferred substituents QVIII, AIII, BIII, EIII, GIII, RIII, YII, WII, T ¹ III, T ² I, T ³ I, T ⁴ I, T ⁵ I, T ⁶ I, XIII, ZII, T ⁷ I, Compounds of the invention having T ⁸ I, U ¹ I and U ² I.

Preferred substituents QIX, AIII, BIII, EIII, GIII, RIII, YII, WII, T ¹ III, T ² I, T ³ I, T ⁴ I, T ⁵ I, T ⁶ I, XIII, ZII, T ⁷ I, Compounds of the invention having T ⁸ I, U ¹ I and U ² I.

Preferred substituents QIII, AV, BIII, EIII, GIII, RIII, YII, WII, T ¹ III, T ² I, T ³ I, T ⁴ I, T ⁵ I, T ⁶ I, XIII, ZII, T ⁷ I, Compounds of the invention having T ⁸ I, U ¹ I and U ² I.

Preferred substituents QIII, AVI, BIII, EIII, GIII, RIII, YII, WII, T ¹ III, T ² I, T ³ I, T ⁴ I, T ⁵ I, T ⁶ I, XIII, ZII, T ⁷ I, Compounds of the invention having T ⁸ I, U ¹ I and U ² I.

Preferred substituents QIII, AVII, BIII, EIII, GIII, RIII, YII, WII, T ¹ III, T ² I, T ³ I, T ⁴ I, T ⁵ I, T ⁶ I, XIII, ZII, T ⁷ I, Compounds of the invention having T ⁸ I, U ¹ I and U ² I.

Q, A, B, E, G, R, R ¹ , Y, Y ¹ , Y ² , W, X, Z, T ¹ , T ² , T ³ , T ⁴ , T ⁵ , T ⁶ , Specific examples of T ⁷ , T ⁸ , U ¹ and U ² are described below.

Halogen atoms in E, G, R, R ¹ , W, X, Y, Y ¹ , Y ² , Y ³ and Z include fluorine atoms, chlorine atoms, bromine atoms and iodine atoms, and preferred are fluorine atoms, chlorine atoms Atom and bromine atom.

B, G, R, R ¹ , T ¹ , T ² , T ³ , T ⁴ , T ⁵ , T ⁶ , T ⁷ , T ⁸ , U ¹ , U ² , W, X, Y, Y ¹ , Y ² The alkyl group at Y ³ and Z is a straight or branched alkyl group having the indicated carbon atom, for example methyl, ethyl, n-propyl, isopropyl, n-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, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1 -Ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, n-heptyl, n-octyl, n-nonyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n Pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl and n-eicosyl, etc. It may be a group.

Alkenyl groups at G, R, R ¹ , T ¹ , T ⁴ , T ⁵ , T ⁶ , Y ¹ and W are linear or branched alkenyl groups with the indicated carbon atoms, for example ethenyl, 1-propenyl, 2-propenyl, 1-butenyl, 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-4-pentenyl, 2 -Methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1, 2-dimethyl-2-butenyl, 1,2-dimethyl-3-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-3-butenyl, 1,1,2-trimethyl- Groups, such as 2-propenyl and 1-ethyl- 1-methyl- 2-propenyl, are mentioned.

Alkynyl groups at E, G, R, R ¹ , Y ¹ and W are linear or branched alkynyl groups with the indicated carbon atoms, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 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 And groups such as 3-butynyl, 2,2-dimethyl-3-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl and 2-ethyl-2-butynyl.

The haloalkyl group at B, E, G, R, R ¹ , T ¹ , W, X, Y, Y ¹ , Y ² , Y ³ and Z is a straight or branched haloalkyl group having the indicated carbon atom, for example fluorine Chloromethyl, chloromethyl, bromomethyl, fluoroethyl, chloroethyl, bromoethyl, fluoro-n-propyl, chloro-n-propyl, difluoromethyl, chlorodifluoromethyl, trifluoromethyl, Dichloromethyl, trichloromethyl, difluoroethyl, trifluoroethyl, trichloroethyl, chlorodifluoromethyl, bromodifluoromethyl, trifluorochloroethyl, hexafluoro-n-propyl, chlorobutyl, And groups such as fluorobutyl, chloro-n-pentyl, fluoro-n-pentyl, chloro-n-hexyl and fluoro-n-hexyl.

Examples of the C ₃ -C ₆ cycloalkyl group optionally substituted by C ₁ -C ₃ alkyl group for G, R, T ¹ , T ⁴ , T ^{5 and} T ⁶ include cyclopropyl, 1-methylcyclopropyl, 2,2, 3,3-tetramethylcyclopropyl, cyclobutyl, 1-ethylcyclobutyl, 1-n-butylcyclobutyl, cyclopentyl, 1-methylcyclopentyl, cyclohexyl, 1-methylcyclohexyl, 4-methylcyclohexyl, etc. Can be mentioned.

B, G, R and T ¹ in the examples of the C ₁ -C ₄ alkyl group substituted by a phenyl group optionally substituted by a C ₁ -C ₄ alkyl group or a halogen atom, a benzyl group, 2-chlorobenzyl, 3-bromobenzyl, 4-chlorobenzyl, 4-methylbenzyl, 4-tert-butylbenzyl, 1-phenylethyl, 1- (3-chlorophenyl) ethyl, 2-phenylethyl, 1-methyl-1-phenylethyl, 1- (4 -Chlorophenyl) -1-methylethyl, 1- (3-chlorophenyl) -1-methylethyl, 1-phenylpropyl, 2-phenylpropyl, 3-phenylpropyl, 1-phenylpropyl, 2-phenylbutyl, 3 -Phenylbutyl, 4-phenylbutyl, 1-methyl-1-phenylpropyl, 1-methyl-2-phenylpropyl, 1-methyl-3-phenylpropyl, 2-methyl-2-phenylpropyl, 2- (4- And groups such as chlorophenyl) -2-methyl-propyl and 2-methyl-2- (3-methylphenyl) propyl.

Examples of the C ₃ -C ₆ cycloalkyl group substituted with a halogen atom or a phenyl group optionally substituted with a C ₁ -C ₄ alkyl group for T ¹ include 1-phenylcyclopropyl, 1- (3-chlorophenyl) cyclopropyl, 1- (4-chlorophenyl) cyclopropyl, 1- (4-bromophenyl) cyclopropyl, 1- (4-fluorophenyl) cyclopropyl, 1- (4-ethylphenyl) cyclopropyl, 1- (4-propyl Phenyl) cyclopropyl, 2-phenylcyclopropyl, 1-phenylcyclobutyl, 2-phenylcyclobutyl, 1-phenylcyclopentyl, 1- (4-chlorophenyl) cyclopentyl, 2-phenylcyclopentyl, 3-phenylcyclo Pentyl, 1-phenylcyclohexyl, 1- (3-fluorophenyl) cyclohexyl, 1- (4-chlorophenyl) cyclohexyl, 1- (4-tert-butylphenyl) cyclohexyl, 2-phenylcyclohexyl, Groups, such as 3-phenylcyclohexyl and 4-phenylcyclohexyl, are mentioned.

Examples of the cyclopropyl group substituted with two groups, a phenyl group optionally substituted by a halogen atom or a C ₁ -C ₄ alkyl group for T ¹ and a C ₁ -C ₄ alkyl group, include 2,2-dimethyl-1-phenylcyclopropyl, 1 -(4-chlorophenyl) -2,2-dimethylcyclopropyl, 2,2-dimethyl-3-phenylcyclopropyl, 3- (3-chlorophenyl) -2,2-dimethylcyclopropyl, (4-chlorophenyl ) -2,2-dimethyl-3-phenylcyclopropyl, (4-bromophenyl) -2,2-dimethyl-3-phenylcyclopropyl, 2,2-dimethyl-3- (4-methylphenyl) cyclopropyl and And groups such as (4-tert-butylphenyl) -2,2-dimethyl-3-phenylcyclopropyl.

Examples of the C ₃ -C ₄ cycloalkyl group substituted with two groups of a halogen atom or a phenyl optionally substituted with a halogen atom or a C ₁ -C ₄ alkoxy group for T ¹ are 2,2-dichloro-1-phenylcyclopropyl, 2 , 2-dichloro-1- (3-chlorophenyl) cyclopropyl, 2,2-dichloro-1- (4-methoxyphenyl) cyclopropyl, 2,2-dichloro-1- (4-ethoxyphenyl) cyclo Propyl, 2,2-dichloro- (4-i-propyloxyphenyl) cyclopropyl, 2,2-dichloro-1- (4-t-butylphenyl) cyclopropyl, 2,2-dichloro-1- (4- And groups such as methoxyphenyl) -3-phenylcyclopropyl and 1- (4-ethoxyphenyl) -2,2,3,3-tetrafluorobutyl.

Examples of the cyclopropyl group substituted with two groups, a C ₂ -C ₄ alkenyl group and a C ₁ -C ₄ alkyl group optionally substituted by a halogen atom in T ^1, are 2,2-dimethyl-3- (2,2-dimethyl Ethenyl) cyclopropyl, 3- (2,2-dibromoethenyl) -2,2-dimethylcyclopropyl, 3- (2,2-chloromoethenyl) -2,2-dimethylcyclopropyl, 3- ( And groups such as 2,2-chlorotrifluoroethenyl) -2,2-dimethylcyclopropyl.

Examples of the C ₃ -C ₆ cycloalkoxy group optionally substituted with a C ₁ -C ₃ alkyl group for T ¹ include cyclopropoxy, cyclobutoxy, cyclopentoxy, cyclohexyloxy and 1-methylcyclopropoxy. The group can be mentioned.

Examples of the C ₂ -C ₄ alkenyl group substituted with a halogen atom or a phenyl group optionally substituted with a C ₁ -C ₄ alkyl group for T ¹ include 1-phenylethenyl, 2-phenylethenyl, and 2- (2-chlorophenyl ) Ethenyl, 2- (3-chlorophenyl) ethenyl, 2- (4-chlorophenyl) ethenyl, 2- (2-methylphenyl) ethenyl, 2- (2,6-difluorophenyl) ethenyl , 2- (2,5-dimethylphenyl) ethenyl, 1-methyl-2-phenylethenyl, 2-phenyl-1-propenyl, 2- (4-bromophenyl) -1-propenyl and 2- And groups such as (2,4,6-trimethylphenyl) -1-propenyl.

Alkoxy groups at G, R, T ¹ , T ² , T ³ , R ¹ , W, X, Y, Y ¹ , Y ² and Z are linear or branched alkoxy groups having the indicated carbon atoms, for example methoxy, Ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentyloxy, 1-methylbutyloxy, 2-methylbutyloxy, 3-methyl Butyloxy, 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-dimethyl Butyloxy, 3,3-dimethylbutyloxy, 1-ethylbutyloxy, 2-ethylbutyloxy, 1,1,2-trimethylpropyloxy, 1,2,2-trimethylpropyloxy, 1-ethyl-1-methyl Propyloxy, 1-ethyl-2-methylpropyloxy, n-heptyloxy, n-octyloxy, n-nonyloxy and n-decyloxy The group can be mentioned.

Examples of C ₃ -C ₆ halocycloalkyl groups for G, R and T ¹ are fluorocyclopropyl, difluorocyclopropyl, chlorocyclopropyl, dichlorocyclopropyl, 1-methyl-2,2-dichlorocyclopropyl, chloro And groups such as cyclobutyl, dichlorocyclobutyl, chlorocyclopentyl, dichlorocyclopentyl, chlorocyclohexyl, dichlorocyclohexyl and tetrafluorocyclobutyl.

Examples of -NU ¹ U ² groups at G, R, R ¹ , T ¹ , W, X, Y, Y ¹ , and Z include methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino , Isobutylamino, sec-butylamino, tert-butylamino, n-pentylamino, 1-methylbutylamino, 2-methylbutylamino, 3-methylbutylamino, 1,1-dimethylpropylamino, 1,2- Dimethylpropylamino, 2,2-dimethylpropylamino, 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-dimethylbutylamino, 3,3-dimethylbutylamino, 1-ethylbutylamino 2-ethylbutylamino, 1,1,2-trimethylpropylamino, 1,2,2-trimethylpropylamino, 1-ethyl-1-methylpropylamino, 1-ethyl-2-methylpropylamino, dimethylamino, Diethylami Furnace, di-n-propylamino, diisopropylamino, di-n-butylamino, di-sec-butylamino, diisobutylamino, di-n-pentylamino, di-n-hexylamino, methylethylamino , Methylpropylamino, methylisopropylamino, methylbutylamino, methyl-sec-butylamino, methyl-isobutylamino, methyl-tert-butylamino, methylpentylamino, methylhexylamino, ethylpropylamino, ethylisopropylamino , Ethylbutylamino, ethyl-sec-butylamino, ethyl-isobutylamino, ethylpentylamino, ethylhexylamino, phenylamino, benzylamino, N-methylacetamido, N-ethylacetamido, N-phenylacet Groups such as amido and N-acetylacetamido, which are indicated by the indicated ranges of their constituent carbon atoms.

Examples of C ₂ -C ₅ alkoxycarbonyl groups at E, G, R, R ¹ , T ¹ , W, X, Y, Y ¹ and Z include methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, and groups such as iso-propoxycarbonyl, n-butoxycarbonyl, sec-butoxycarbonyl, iso-butoxycarbonyl and tert-butoxycarbonyl.

The C ₁ -C ₄ haloalkoxy groups at G, R, T ¹ , W, X, Y, and Z are linear or molecular C ₁ -C ₄ haloalkoxy groups, for example fluoromethoxy, difluoromethoxy , Trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, dichlorofluoromethoxy, chloromethoxy, dichloromethoxy, trichloromethoxy, bromomethoxy, fluoroethoxy, chloroethoxy, bromo Methoxy, difluoroethoxy, trifluoroethoxy, tetrafluoroethoxy, pentafluoroethoxy, trichloroethoxy, trifluorochloroethoxy, fluoropropoxy, chloropropoxy, bromoprop And groups such as foxy, fluorobutoxy, chlorobutoxy, fluoro-iso-propoxy and chloro-iso-propoxy.

Examples of C ₁ -C ₄ alkylsulphenyl groups at E, G, R, T ² , T ³ , W, X, Y and Z are methylthio, ethylthio, n-propylthio, iso-propylthio, n-butyl And groups such as thio, iso-butylthio, sec-butylthio and tert-butylthio.

Examples of C ₁ -C ₄ alkylsulfinyl groups at E, G, R, X, W, Y and Z include methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, iso-propylsulfinyl, n-butylsulfinyl and groups such as iso-butylsulfinyl, sec-butylsulfinyl and tert-butylsulfinyl.

Examples of C ₁ -C ₄ alkylsulfonyl groups at B, E, G, R, W, X, Y and Z are methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, iso-propylsulfonyl, n-butyl And groups such as sulfonyl, iso-butylsulfonyl, sec-butylsulfonyl and tert-butylsulfonyl.

Examples of C ₂ -C ₄ alkoxyalkyl groups at B, G, R, R ¹ , T ¹ , Y, Y ¹ and Y ² are C ₁ -C ₃ alkoxy-methyl, C ₁ -C ₂ alkoxy-ethyl, methoxy And groups such as ethoxymethyl and methoxypropyl.

Examples of C ₂ -C ₄ alkylcarbonyl groups at E, G, R, R ¹ , U ¹ , U ¹ , Y ¹ , Y ² and W include groups such as acetyl, propionyl, butanoyl and iso-butanoyl. have.

Examples of the C ₂ -C ₆ haloalkylcarbonyl group in G and W include groups such as chloroacetyl, trifluoroacetyl, 3,3,3, -trifluoropropionyl and pentafluoropropionyl.

Examples of C ₂ -C ₅ haloalkylcarbonyloxy groups at G, R and Y include chloroacetyloxy, trifluoroacetyloxy, 3,3,3, -trifluoropropionyloxy and pentafluoropropionyloxy Etc. are mentioned.

Examples of the C ₃ -C ₇ dialkylaminocarbonyloxy group in G and Y include groups such as dimethylaminocarbonyloxy, diethylaminocarbonyloxy and di-i-propylaminocarbonyloxy.

Examples of the naphthyl group in R, Y, Z and T ¹ include groups such as 1-naphthyl and 2-naphthyl.

Examples of the pyridyl group optionally substituted by Z in G and T ¹ include 2-pyridyl, 3-pyridyl and 4-pyridyl, all of which are optionally substituted by Z. Preferred of these are all 2-pyridyl groups and 3-pyridyl groups optionally substituted by Z, and more preferred are 2-pyridyl groups optionally substituted by Z.

Examples of the pyridyloxy group optionally substituted by Z in G and T ¹ include a 2-pyridyloxy group, a 3-pyridyloxy group and a 4-pyridyloxy group, all of which are optionally substituted by Z.

Examples of the pyridyl group optionally substituted by X in R and R ¹ include a 2-pyridyl group, a 3-pyridyl group and a 4-pyridyl group, all of which are optionally substituted by X. Preferred of these are all 2-pyridyl groups and 3-pyridyl groups optionally substituted by X, and more preferred are 2-pyridyl groups optionally substituted by X.

Examples of pyridyloxy group optionally substituted by X for R and R ¹ are 2-pyridyloxy group, 3-pyridyloxy group and 4-pyridyloxy group, all of which are optionally substituted by X.

Examples of the thienyl group optionally substituted by X in R and R ¹ include a 2-thienyl group and a 3-thienyl group, all of which are optionally substituted by X.

Examples of the thienyl group optionally substituted by Z in G and Y ¹ include a 2-thienyl group and a 3-thienyl group, all of which are optionally substituted by Z.

-N = CT ⁷ T ⁸ in G, R, R ¹ , Y, and Y ¹ represents an alkylideneamino group, a benzylideneamino group, an arylideneamino group or a cycloalkylideneamino group, such as methylideneamino, ethylideneamino And groups such as propylideneamino, isopropylideneamino, 4-methyl-2-pentylideneamino, cyclopentylideneamino and cyclohexylideneamino.

Examples of the C ₂ -C ₄ alkylaminocarbonyl group in E include groups such as methylaminocarbonyl, ethylaminocarbonyl and n-propylaminocarbonyl.

Examples of C ₃ -C ₉ dialkylaminocarbonyl groups in E include dimethylaminocarbonyl, diethylaminocarbonyl, di-n-propylaminocarbonyl, di-isopropylaminocarbonyl and di-n-butylaminocarbonyl Etc. are mentioned.

Examples of the C ₁ -C ₄ alkylaminosulfonyl group in B include groups such as methylaminosulfonyl, ethylaminosulfonyl, n-propylaminosulfonyl, isopropylaminosulfonyl and n-butylaminosulfonyl.

Examples of C ₂ -C ₈ dialkylaminosulfonyl groups in B include dimethylaminosulfonyl, diethylaminosulfonyl, di-n-propylaminosulfonyl, di-isopropylaminosulfonyl and di-n-butylaminosul Groups, such as a ponyl, are mentioned.

Examples of C ₂ -C ₅ alkylaminothiocarbonyl groups in B include methylaminothiocarbonyl, ethylaminothiocarbonyl, n-propylaminothiocarbonyl, isopropylaminothiocarbonyl, n-butylaminothiocarbonyl, and the like. The group can be mentioned.

Examples of C ₃ -C ₉ dialkylaminothiocarbonyl groups in B include dimethylaminothiocarbonyl, diethylaminothiocarbonyl, di-n-propylaminothiocarbonyl, di-isopropylaminothiocarbonyl and di-n And groups such as -butylaminothiocarbonyl.

B of a halogen atom or a C ₁ -C ₄ alkyl group optionally substituted with a substituted benzoyl C ₁ -C ₄ learned by kalgi in example phenacyl, 2-Fluoro-phenacyl, 3-chloro phenacyl, 4-bromo And groups such as phenacyl, 2-methylphenacyl, 3-ethylphenacyl, 4-i-propylphenacyl, and 4-t-butylphenacyl.

Examples of the phenylsulfonyl group optionally substituted by a halogen atom or a C ₁ -C ₄ alkyl group in B include 2-fluorophenylsulfonyl, 4-fluorophenylsulfonyl, 2-chlorophenylsulfonyl, 4-chlorophenylsul Ponyl, 4-bromophenylsulfonyl, 2,5-dichlorophenylsulfonyl, pentafluorophenylsulfonyl, 4-methylphenylsulfonyl, 2-methylphenylsulfonyl, 4-t-butylphenylsulfonyl, 2,5 And groups such as -dimethylphenylsulfonyl, 2,4-dimethylphenylsulfonyl, 2,4,6-trimethylphenylsulfonyl and 2,4,6-tri-i-propylphenylsulfonyl.

Examples of the C ₂ -C ₅ cyanoalkyl group in G and B include groups such as cyanomethyl, 2-cyanoethyl, 3-cyanopropyl, and 1-cyano-1-methylethyl.

The C ₃ -C ₉ alkoxycarbonylalkyl group in B is linear or branched, for example methoxycarbonylmethyl, ethoxycarbonylmethyl, n-propoxycarbonylmethyl, i-propoxycarbonylmethyl , n-butoxycarbonylmethyl, i-butoxycarbonylmethyl, t-butoxycarbonylmethyl, n-hexyloxycarbonylmethyl, n-heptyloxycarbonylmethyl, 1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-n-butoxyethyl, 2-methoxycarbonylethyl, 2-ethoxycarbonylethyl, 1-methoxycarbonylpropyl, 3-ethoxycarbonylpropyl, 4- Methoxycarbonylbutyl, 6-ethoxycarbonylhexyl, 1-methoxycarbonyl-1-methylethyl, 1-iso-propoxycarbonyl-1-methylethyl and 1-ethoxycarbonyl-2-methyl And groups such as profiles.

Examples of alkali metals in B include lithium, sodium and potassium.

Examples of alkaline earth metals in B include magnesium, calcium, strontium and barium, with magnesium, calcium and barium being preferred.

Examples of the ammonium group of NHT ⁴ T ⁵ T ⁶ for B include ammonium, monomethylammonium, dimethylammonium, trimethylammonium diethylammonium, triethylammonium, di-isopropylammonium, di-isopropylethylammonium, hexylmethylammonium, cyclo And groups such as propylmethylammonium, cyclohexylmethylammonium, allylmethylammonium, benzylmethylammonium and 4-methylcyclohexylethylammonium. Two of T ⁴ , T ⁵ and T ⁶ may form heterocyclic 5, 6, 7 or 8 membered ammonium groups optionally with oxygen, nitrogen and / or sulfur atoms in addition to the nitrogen atoms to which they are attached.

Examples of methoxy groups substituted with a phenyl group optionally substituted with halogen or C ₁ -C ₄ alkyl for G include benzyloxy, 2-chlorobenzyloxy, 3-chlorobenzyloxy, 4-chlorobenzyloxy, 3-methoxybenzyl And groups such as oxy, 4-t-butylbenzyloxy, 2,6-difluorobenzyloxy and 2-fluoro-4-chlorobenzyloxy.

Examples of heterocyclic 5, 6, 7 or 8 membered ammonium groups having the oxygen, nitrogen and / or sulfur atoms formed by two of T ⁴ , T ⁵ and T ⁶ in addition to the nitrogen atoms to which T ⁴ , T ⁵ and T ⁶ bind Groups such as pyrrolidine, pyrazolidine, imidazolidine, oxazolidine, isoxoxazolidine, thiazolidine, piperidine, piperazine, morpholine, thiamorpholine, hexamethyleneimine and heptamethyleneimine Can be mentioned.

Haloalkylsulphenyl groups at G, R, W, X, Y and Z are linear or branched C ₁ -C ₄ haloalkylthio groups, such as fluoromethylthio, chlorodifluoromethylthio, bromodifluoro Romethylthio, trifluoromethylthio, trichloromethylthio, 2,2,2-trifluoroethylthio, 1,1,2,2-tetrafluoroethylthio, fluoroethylthio, pentafluoroethyl And groups such as thio and fluoro-iso-propylthio.

Haloalkylsulfinyl groups at G, R, W, X, Y and Z are linear or branched C ₁ -C ₄ haloalkylsulfinyl groups, for example fluoromethylsulfinyl, chlorodifluoromethylsulfinyl, Bromodifluoromethylsulfinyl, trifluoromethylsulfinyl, trichloromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 1,1,2,2-tetrafluoroethylsulfinyl, fluoro And groups such as roethylsulfinyl, pentafluoroethylsulfinyl and fluoro-iso-propylsulfinyl.

Haloalkylsulfonyl groups at G, R, W, X, Y and Z are linear or branched C ₁ -C ₄ haloalkylsulfonyl groups, for example fluoromethylsulfonyl, chlorodifluoromethylsulfonyl, Bromodifluoromethylsulfonyl, trifluoromethylsulfonyl, trichloromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 1,1,2,2-tetrafluoroethylsulfonyl, fluoro And groups such as roethylsulfonyl, pentafluoroethylsulfonyl and fluoro-isopropylsulfonyl.

Haloalkenyl groups at G, R, T ¹ and W are linear or branched C ₂ -C ₄ haloalkenyl groups, examples being 2-chloroethenyl, 2-bromoethenyl and 2,2-dichloroethenyl Etc. are mentioned.

Alkenyloxy groups at G, R, R ¹ , T ¹ , W, Y and Y ¹ are linear or branched C ₂ -C ₄ alkenyloxy groups, examples being allyloxy, 2-propenyloxy, 2- And groups such as butenyloxy and 2-methyl-2-propenyloxy.

Haloalkenyloxy groups at G, R, W and Y are linear or branched C ₂ -C ₄ haloalkenyloxy groups, for example 3-chloro-2-propenyloxy, 3,3-dichloro-2- And groups such as propenyloxy, 4-chloro-2-butenyloxy, 4,4-dichloro-3-butenyloxy, and 4,4-difluoro-3-butenyloxy.

Alkenylsulphenyl groups at G, R, W, X, Y and Z are linear or branched C ₂ -C ₄ alkenylsulphenyl groups, examples being allylsulphenyl, 2-propenylsulphenyl, 2-butenylsulphenyl And groups such as 2-methyl-2-propenylsulphenyl.

Alkenylsulfinyl groups at G, R, W, X, Y and Z are linear or branched C ₂ -C ₄ alkenylsulfinyl groups, for example allylsulfinyl, 2-propenylsulfinyl, 2-butenylsul And groups such as pinyl and 2-methyl-2-propenylsulfinyl.

Alkenylsulfonyl groups at G, R, W, X, Y and Z are linear or branched C ₂ -C ₄ alkenylsulfonyl groups, examples being allylsulfonyl, 2-propenylsulfonyl, 2-butenylsul Groups, such as a ponyl and 2-methyl- 2-propenyl sulfonyl, are mentioned.

The haloalkenylsulphenyl group at G, R, W and Y is a linear or branched C ₂ -C ₄ haloalkenylsulphenyl group, for example 3-chloro-2-propenylsulphenyl, 4-chloro-2-bute And groups such as 3,3-dichloro-2-propenylsulphenyl, 4,4-dichloro-3-butenylsulphenyl, and 4,4-difluoro-3-butenylsulphenyl.

The haloalkenylsulfinyl groups at G, R, W and Y are linear or branched C ₂ -C ₄ haloalkenylsulfinyl groups, for example 3-chloro-2-propenylsulfinyl, 3,3-dichloro- And groups such as 2-propenylsulfinyl, 4-chloro-2-butenylsulfinyl, 4,4-dichloro-3-butenylsulfinyl, and 4,4-difluoro-3-butenylsulfinyl.

The haloalkenylsulfonyl groups at G, R, W and Y are linear or branched C ₂ -C ₄ haloalkenylsulfonyl groups, for example 3-chloro-2-propenylsulfonyl, 3,3-dichloro- And groups such as 2-propenylsulfonyl, 4-chloro-2-butenylsulfonyl, 4,4-dichloro-3-butenylsulfonyl, and 4,4-difluoro-3-butenylsulfonyl.

Examples of C ₂ -C ₄ haloalkynyl groups at G, R and W include chloroethynyl, bromoethynyl, iodoethynyl, 3-chloro-1-propynyl and 3-bromo-1-butynyl, and the like. The group can be mentioned.

Examples of the C ₂ -C ₄ alkynyloxy group for G, R, W and Y include groups such as 2-propynyloxy, 2-butynyloxy and 1-methyl-2-propynyloxy.

Examples of C ₂ -C ₄ haloalkynyloxy groups at G, R, W and Y are 3-chloro-2-propynyloxy, 3-bromo-2-propynyloxy and 3-iodo-2-propynyl And groups such as oxy.

Examples of the C ₂ -C ₆ alkynylsulphenyl group for G, R, W and Y include groups such as 2-propynylsulphenyl, 2-butynylsulphenyl and 1-methyl-2--propynylsulphenyl.

Examples of the C ₂ -C ₆ alkynylsulfinyl group at G, R, W and Y include groups such as 2-propynylsulfinyl, 2-butynylsulfinyl and 1-methyl-2--propynylsulfinyl.

Examples of the C ₂ -C ₆ alkynylsulfonyl group in G, R, W and Y include groups such as 2-propynylsulfonyl, 2-butynylsulfonyl and 1-methyl-2--propynylsulfonyl.

Examples of C ₂ -C ₆ haloalkynylsulphenyl groups at G, R, W and Y are 3-chloro-2-propynylsulphenyl, 3-bromo-2-propynylsulphenyl and 3-iodo-2-propynylsul And groups such as phenyl.

Examples of C ₂ -C ₆ haloalkynylsulfinyl groups at G, R, W and Y are 3-chloro-2-propynylsulfinyl, 3-bromo-2-propynylsulfinyl and 3-iodo-2-propy Groups, such as a nil sulfinyl, are mentioned.

Examples of C ₂ -C ₆ haloalkynylsulfonyl groups at G, R, W and Y are 3-chloro-2-propynylsulfonyl, 3-bromo-2-propynylsulfonyl and 3-iodo-2-propy And groups such as nilsulfonyl.

Examples of the C ₂ -C ₄ alkylcarbonyloxy group in G, R, W and Y include groups such as acetoxy, propanoyloxy, butanoyloxy and isopropylcarbonyloxy.

Examples of the benzoyl group optionally substituted by X for E and G include benzoyl, 2-chlorobenzoyl, 3-chlorobenzoyl, 4-chlorobenzoyl, 4-bromobenzoyl, 4-fluorobenzoyl, 3-methylbenzoyl, 4 And groups such as -methylbenzoyl, 4-tert-butylbenzoyl and 3,4-dichlorobenzoyl.

The compounds of the present invention can be used in low concentrations, such as so-called agricultural pests that damage agricultural crops, horticultural crops and trees, so-called livestock pests parasitic in livestock and poultry, so-called sanitary pests that have various adverse effects on human dwelling environments, including houses, Effectively controlling various insects and small animals, including mite, nematodes, molluscs and crustaceans, etc., which damage so-called stored product pests stored in warehouses, and which live in the same places as above and damage the above.

Examples of pests, mites, nematodes, molluscs and crustaceans, which can be eradicated by the compounds of the present invention, are not limited but are as follows.

Diamond-patterned moths ( Plutella xylostella Linne), Chilo suppressalis Walker, Rice Leafworm ( Cnaphalocrosis medinalis Guenee), Rice Lepidoptera Larva ( Naranga aenescens Moore), Rice Leaf Butterfly ( Parnara guttata Bremer et Gvey) ), Cabbage antlers ( Mamestra brassicae Linne), common white butterfly ( Pieris rapae crucivora Boisduval), turnip moth ( Agrotis segetum Denis et Schiffermuller), common beetle ( Spodptera litura Fabricius), beet beetle ( Spodoptera exigua Hubner), Small Tea Leaf Moth ( Adoxophyes sp.), Oriental Tea Leaf Moth ( Homona magnanima Diakonoff), Peach Moth ( Carposina niponensis Walsingham), Yellow Wedge Moth ( Grapholita molesta Busck), Summer Fruit Leaf Moth ( Adoxophyes orana fasciata Walsingham), Apple Leaf minor (Phyllonorycter ringoniella Matsumura), corn ear worm (Helicoverpa zea Boddie), tobacco bed bugs (Heliothis virescens Fabricus), European prison Can nabiryu pests such borer (Ostrinia nubilalis Hubner), fall destroy gangchung (Spodoptera frugiperda JE Smith), kodeul ring moth (Cydia pomonella Linne), fall honeycomb moth (Hyphantria cunea Drury);

Green rice end maemichung (Nephotettix cincticeps Uhler), brown Brown Planthopper (Nilaparvata lugens Stal), green peach aphid (Myzus persicae Sulzer), cotton aphid (Aphis gossypii Glover), greenhouse whitefly (Trialeurodes vaporariorum Westwood), potato whitefly (Bemisia tabaci Gennadius) fold four ILA (Psylla pyricola Forster), rhododendron shield bug (Stephanitis pyroides Scott), arrowhead scale (Unaspis yanonensis Kuwana), powdered pod worm (Pseudococcus comstocki Kuwana), red wax scale (Ceroplastes rubens Maskell), brown fart worms ( Cicada pests such as Halyomorpha mista Uhler, cabbage beetle ( Eurydema rugosam Motschulsky), and bedbugs ( Cimex lectularius Linne);

20 spotted ladybugs (Henosepilachnas vigintioctopunctata Fabricius), copper Bill beetle (Anomala cuprea Hope), nonmul weevil (Lissorhoptrus oryzophilus Kuschel), sweet potato weevil (Cylas formicarius Fabricius), cucurbit leaf beetle (Aulacophora femoralis Motschulsky), striped flea (Phyllotreta striolata Fablicius ), the white-spotted long tactile beetle (anoplophora malasiaca Thomson), sawyer (Monochamus alternatus Hope), corn geunchung (Diabrotica spp.), rice weevil (Sitophilus zeamais Motschulsky), small rice weevil (Sitophilus oryzae Linne), granary weevil ( Pests belonging to the coleoptera , such as Sitophilus granarius Linne), Tribolium castaneum Herbst;

Liriomyza trifolii Burgess, Seed Corn Maggot ( Delia platura Meigen), Mayetiola destructor Say, Melon Fly ( Dacus ( Zengodacus ) cucurbitae Coquillett), Ceratitis capitata Wiedemann, Housefly ( Musca domestica Linne), Cowfly ( Stomoxys calcitrans Linne), Sheep Mite ( Melophagus orinus ), Common Cowfly ( Hypoderm lineatum devillers), Northern Cowfly ( Hypoderma boris Linne), Sheep fly ( Oestrus ovis Linne) Insects belonging to the fly, such as ( Golossina palpalis Robineau-Desvoidy), common mosquito ( Culex pipiens pallens Coquillett), yellow fever mosquito ( Aedes aegypti Linne), Anopheles culicifacies ;

Pests belonging to felling such as cabbage leaf beetle ( Atthys rosae ruficornis Jakovlev), pine needle bee ( Neodiprion sertifer Geaffroy), chestnut bee ( Apethymus kuri Takeuchi);

Clover beetles, such as the melon whiskers ( Thrips palmi Karny), onion whiskers ( Thrips tabaci Lindeman), Western flower whiskers ( Frankliniella occidentalis Pergande), flower whiskers ( Frankliniella intonsa Trybom), yellow tea whiskers ( Scirtothrips dorsalis Hood) Pests belonging to the neck;

Pests belonging to cockroaches such as light brown cockroach ( Periplaneta fuliginosa Serville), Japanese cockroach ( Periplaneta japonica Karny), and German cockroach ( Blattella germanica Linne);

Pests belonging to the grasshoppers, such as Locusta migratoria Linne, rice grasshopper ( Oxya yezoensis Shiraki), and desert grasshopper ( Schistocerca gregaria Forskal);

Pests belonging to termites such as Coptotermes formosanus Shiraki from Taiwan, Reticulitermes ( Leucotermes speratus Kolbe), and ( Odontotermes formosanus Shirakif);

Pests belonging to fleas such as cat fleas ( Ctenocephalides felis Bouche), human fleas ( Plex irritans Linne) and oriental rat fleas ( Xenopsylla cheopis Rothschild);

Pests belonging to the hairy tree such as chickens ( Menacanthus stramineus Nitsch), bovine vampires ( Bovicola bovis Linne);

Pests belonging to the eyes of the short nose cow ( Haematopinus eurysternus Nitzsh), pig teeth ( Haematopinus suis Linne), long nose cow ( Linognathus vituli Linne), small cow ( Solennopotes capillatus Enderlein);

Pests of tetranichide such as citrus red mite ( Panonychus citri Mcgregor), European red mite ( Panonychus ulmi Kock), two-pointed spider mite ( Tetranychus urticae Koch), Kanza spider mite ( Tetranychus Kanzawai Kishida);

Pink citrus nokgyun bottle mite (Aculops pelekassi Keifor), black eungaegwa pests such as mites baenokgyun bottle (Epitrimerus pyri Nalepa), dry bulb mite (Aceria tulipae Keiter), pink tea mite (Acaphylla theae watt);

Pocket mites and pests such as Bromine mite ( Polyphagotarsonemus latus Banks), cyclamen mites, and strawberry mites ( Steneotarsonemus pallidus Banks);

Fungi and pests such as fungal mites, palm mites, fodder mites ( Tirophagus putrescetiae Schrank), bulbous mites ( Rhizoglyphus robini Claparede);

Pterodactyl pests, such as the varroa jacobsoni Oudemans ;

Cattle tick (Boophilus microplus canestrini), indeed in pest mites, such as (Haemaphysalis longicornis Neumann);

Scabies pests such as perforated insects and scabies mites ( Sarcaptes scabiei Linne);

Southern root-knot nematode (Meloidogyne incognita Kofoid et White), northern root-knot nematode (Meloidogyne hapla Chitwood), Cobb rot nematode (Pratylenchus penetraua Cobb), walnut wood rot nematode (Pratylenchus vulnus Allen et Jensen), potato cyst nematode (Globodera rostochiensis Wollenweber Nematodes such as Bursaphelenchus xylophilus Steiner et Buhrer;

Mollusks such as the apple snail ( Pomacea canaliculata Lamarck), ( Incilaria pilineata Benson), ( Acusta despecta sieboldiana Pfeiffer), ( Euhadra peliomphala Pfeiffer), and Armadillidium vulgare Latreille;

Shellfish such as Armadillidium vulgare Latreille;

Plant diseases that can be controlled by the compounds of the present invention are as follows:

Pyricularia oryzae of rice, parasite spore leaf spot ( Cochliobolus miyabeanus ) and staining disease ( Rhizoctonia solani ),

Barley and wheat powdery mildew (Erysiphe graminis f. Sp. Hordei . F. Sp. Tritici), leaf lines rust (Pyrenophora graminea), Net Pattern (Pyrenophora teres), tobacco blight (Gibberella zeae), yellow rust, black stem rust and red rust (Puccinia striiformis, P. graminis, P. recondita and P. hordei), snow blight and snow mold (Typhulaza sp. Micronectriella nivais), such kkambugi (Ustilago tritici, U. nuda), nunkkol blotch (Pseudocercorsporella herpotrichoides), Spot disease ( Rhynchosporium secalis ), spot patterns ( Septoria tritici ), and blemishes ( Leptosphaeria nodorum ),

Mill scale species of citrus (Diaporthe citri), red mold disease (Elsinoe fawcetti), and usually green mold and blue mold (Penicillium digitatum, P. italicum),

Apple blight ( Sclerotinia mali ), root disease ( Valsa mali ), powdery mildew ( Podosphaera leucotricha ), Alternaria mali and red fungus ( Venturia inaequalis ),

Red fungus ( Venturia nashicola ), black spots ( Alternaria Kikuchiana ) and rust disease ( Gymnosporangium haraeanum ) in pears ,

Peach brown rot ( Sclerotinia cinerea ), red fungus ( Cladosporium carpophilum ), and phomopsis sp.

Grape fungus ( Plasmopara viticola ), anthrax ( Elsinoe ampelina ), purulent rot ( Glomerella cingulata ), powdery mildew ( Uncinula necator ) and rust ( Phakopsora ampelopsidis ),

Persimmon anthracnose ( Gloesporium kaki ), powdery mildew ( Phyllactinia kakicola), hairy pattern ( Cercospora kaki ), and circular pattern disease ( Mycosphaerella nawae),

Gourd's Pseudoperenospora cubensis , anthrax ( Colletotrichum lagenarium ), powdery mildew ( Sphaerotheca fuliginea ), and rubbery stem blight ( Mycosphaerella melonis ),

Late blight of tomatoes ( Phytophthora infestans ), early blight ( Alternaria solani ) and leaf fungus ( Cladosporium fulvam ),

Brown spot disease ( Phomopsis vexans ) and powdery mildew ( Erysiphe cichoracoarum ),

Alternaria japonica and Creecosporella brassicae of mustard plants,

Rust of Wales onion ( Puccinia allii ),

Purple seed stain disease of soybean (Cercospora kikuchii), necrotizing red mold disease (Elsinoe glycines) and port and stem blight (Diaporthe phaseololum),

Anthrax of Collective beans ( Collectorichum lindemuthianum ),

Leaf spots of peanuts ( Mycosphaerella personatum ) and brown leaf spots ( Cercospora arachidicola ),

Pea powdery mildew (Erysiphe pisi),

Detection of early blight ( Alternaria solani ),

Powdery mildew ( Sphaerotheca humuli ),

Reticulum ( Exobasidium reticulatum ) and white fungus ( Elsinoe leucospila ) in tea ,

Tobacco spots ( Alternaria longipes ), powdery mildew ( Erysiphe cichoracearum ) and anthrax ( Colletotrichum tabacum ),

Vesicular leaf spots of beet ( Cercospora beticola ),

Rose spots ( Diplocarpon rosae ) and powdery mildew ( Sphaerotheca pannosa ),

Chrysanthemum leaf spot ( Septoria chrysanthemiindici ) and rust ( Puccinia horiana ),

Gray mold of various crops ( Botrytis cinerea ), and

Sclerotinia of various crops ( Sclerotinia sclerotiorum ).

Moreover, the compounds of the present invention are effective for preventing adhesion of aquatic organisms even at extremely low concentrations. Examples of the aquatic organisms to which the present invention relates include mussels, barnacles, oysters, hydroworms, hydra tonic animals, Serpula , locusts, mud pond snails, greens , shellfish such as Ectocarpus and algae.

Specifically, the compounds of the present invention, even when used at low concentrations, are effective against various harmful small animals, pests and phytopathogenic microorganisms such as grasshoppers, cicadas, butterflies, beetles, bees, flies, temitides, mites and muds. Can eradicate it. Moreover, the compounds of the present invention effectively prevent the attachment of various aquatic organisms living in seawater and freshwater to underwater constructs and the like. On the other hand, the compounds of the present invention contain useful compounds that have little adverse effect on mammals, fish, shellfish and useful insects.

Compounds having CN as E in the compounds of the present invention can be prepared according to the following method (Reaction Scheme 1: reaction scheme 1).

Reaction Summary 1:

(Method A)

(Method B)

(Method C)

In (Scheme Summary 1), Q, A and B have the same meaning as defined above, and L represents a suitable leaving group, for example, a chlorine atom, a bromine atom, an iodine atom, an alkoxy group having 1 to 4 carbon atoms, and a phenoxy group. , Alkylsulfonyloxy group having 1 to 4 carbon atoms, benzenesulfonyloxy group, toluenesulfonyloxy group, phenoxy group, 1-pyrazolyl group or 1-imidazolyl group, L 'represents a halogen atom, and Alkyl preferably represents an alkyl group having 1 to 4 carbon atoms.

Method A in (Scheme Summary 1) reacts an acetonitrile derivative of formula (3) with an acid chloride, ester or amide of formula (4), or with an acid anhydride of formula (5) to give a compound of the present invention. To get 1 '. Compound (1 ') of the present invention is optionally reacted with an alkyl halide, alkyl sulfonate, trimethylsilyl halide, sulfonyl chloride, sulfamoyl chloride, thiocarbamoyl chloride, acid chloride or ester of formula (8) Convert to compound (1). According to the kind of B in the compound (1) of this invention, a compound (1) is obtained by making compound (1 ') react with dihydropyran, an isocyanate, or a thioisocyanate. In the method A, when the compound of Formula (4) or (5) is used in excess, Compound (1) can be obtained directly without separating Compound (1 ').

When Q is bonded to the acrylonitrile moiety through a nitrogen atom, compound (1 ') may be prepared according to Method B. Method B is to react the heterocyclic compound of formula (6) with the halogenocyanoketone of formula (7) to obtain compound (1 ') of the present invention.

When A is bonded to the acrylonitrile moiety through a nitrogen atom, compound (1 ') may be prepared according to Method C. Method C is to react the cyanoacetic acid derivative of formula (9) with a heterocyclic compound of formula (10) to obtain compound (1 ') of the present invention. In either case, the compound of formula (9) is prepared by reacting the acetonitrile derivative of formula (3) with the carboxylic acid ester in the presence of a base as used in Method A.

Compounds in which E in the compounds of the present invention are the following can be prepared according to the following method (Reaction Scheme 2).

Reaction Summary 2:

(Method D)

(Method E)

(Method F)

In (Scheme Summary 2), Q, A, E, B, L, L 'and alkyl are the same as defined above.

Method D in (Scheme Summary 2) is carried out by reacting a compound of formula (11) with an acid chloride, ester or amide of formula (4) or with an acid anhydride of formula (5) (1) ') To get. Compound (1 ') of the present invention is optionally reacted with an alkyl halide, alkyl sulfonate, trimethylsilyl halide, sulfonyl chloride, sulfamoyl chloride, thiocarbamoyl chloride, acid chloride or ester of formula (8) Convert to compound (1). According to the kind of B in the compound (1) of this invention, a compound (1) is obtained by making compound (1 ') react with dihydropyran, an isocyanate, or a thioisocyanate. In the method A, when the compound of Formula (4) or (5) is used in excess, Compound (1) can be obtained directly without separating Compound (1 ').

When Q is bonded to the ethylene moiety through a nitrogen atom, compound (1 ') may be prepared according to Method E. Method E is to react the heterocyclic compound of formula (6) with the compound of formula (12) in the presence of a base to obtain compound (1 ') of the present invention.

When A is bonded to the ethylene moiety through a nitrogen atom, compound (1 ') may be prepared according to Method F. Method F is to react the compound of formula (13) with the heterocyclic compound of formula (10) by dealcoholation to obtain compound (1 ') of the present invention. In either case, the compound of formula (13) is prepared by reacting the compound of formula (11) with the carboxylic acid ester in the presence of a base as used in Method D.

If necessary, compound (1 ') in which E is an alkoxycarbonyl group is hydrolyzed, decarboxylated and halogenated to obtain a compound of the present invention in which E is a halogen atom. In either case, a compound of the present invention, wherein E is a halogen atom, is used as a nucleophilic reagent corresponding to E (e.g. triester phosphite, alkyl mercaptan, thiophenol, metal acetylide, metal cyanide, metal azide, nitrile) The reaction may also yield different compounds of the invention. In any case, the compound of the present invention may be obtained by reacting a compound obtained by dicarboxylation of compound (1 ′), wherein E is an alkoxycarbonyl group, with an electrophilic reagent under basic conditions.

In either case, it is preferable to carry out each of the steps of (Scheme Summary 1) and (Scheme Summary 2) in the presence of a base. Examples of bases used include alkali metal alkoxides such as sodium ethoxide, sodium methoxide and t-butoxy potassium; Alkali metal hydroxides (eg sodium hydroxide, potassium hydroxide); Alkali metal carbonates such as sodium carbonate and potassium carbonate; Organic bases (eg triethylamine, pyridine, DBU); Organolithium compounds such as butyl lithium; Lithium amides such as lithium diisopropylamide, lithium bistrimethylsilylamide; And sodium hydride.

The reaction of (Reaction Outline 1) and (Reaction Outline 2) may be carried out in a solvent which is inert to the reaction. As an example of this solvent, Lower alcohols, such as methanol and ethanol; Aromatic hydrocarbons such as benzene and toluene; Ethers such as diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane and 1,2-diethoxyethane; Halogenated hydrocarbons such as methylene chloride, chloroform and 1,2-dichloroethane; Amides such as dimethylformamide and dimethylacetamide; Acetonitrile; Dimethyl sulfoxide; And mixed solvents thereof. Depending on the case, a mixed solvent of the solvent and water may also be used. In addition, if desired, quaternary ammonium salts such as tetra-n-butylammonium bromide can be added to the reaction system as a catalyst to obtain good results. The reaction temperature is in the range of -30 ° C to 200 ° C, and the reaction temperature is preferably between 0 ° C to 150 ° C or 0 ° C to the boiling point of the solvent used. The base is used in an amount of 0.05 to 10 equivalents, preferably 0.05 to 3 equivalents, based on the reactor mass.

Compounds of the invention are separated from the reaction mixture by conventional methods. When purification of the compound of this invention is needed, it can isolate | separate and refine | purify by conventional methods, such as recrystallization or column chromatography, for example.

Among the compounds of the present invention, those having asymmetric carbon atoms include (+) and (-) photoactive compounds.

The manufacturing method of compound (3) used by (Reaction summary 1) is demonstrated below. These compounds (3) can be prepared according to the following (Scheme Summary 3).

Reaction Summary 3:

1) A halogenated benzyl, benzyl alkylsulfonate, benzyl arylsulfonate, halomethyl-heterocyclic compound, alkylsulfonyloxymethyl-heterocyclic compound or arylsulfonyloxymethyl-heterocyclic compound of the formula (14) To react with compound (3). Alternatively, the phenylacetic acid derivative or the heterocyclic acetic acid derivative is converted into the corresponding amide derivative. Dehydration gives compound (3).

2) The heterocyclic halide (15) is condensed with cyanoacetate (16) in the presence of a base to give compound (17), which is then hydrolyzed and decarboxylated to give compound (3).

3) To obtain a compound (3) in which Q is bonded to the ethylene moiety through a nitrogen atom, a heterocyclic derivative (6) having an unsubstituted nitrogen atom of Q is reacted with a haloacetonitrile derivative in the presence of a base. As another method, compound (17) is obtained by reacting compound (6) with compound (18) in the presence of a base, which is obtained by halogenation of cyanoacetate. Subsequently, compound (17) is hydrolyzed and decarboxylated to obtain compound (3).

Compound (11) used in (Scheme Summary 2) can be produced by the same method as in the preparation of compound (3) described above.

Compound (7) to be used in (Scheme Summary 1) can be prepared by subjecting a benzoic acid halide or heterocyclic carboxylic acid halide to cyanoacetate in the presence of a base, and then halogenating the resulting condensate.

The halomethyl-heterocyclic compounds, alkylsulfonyloxymethyl-heterocyclic compounds and arylsulfonyloxymethyl-heterocyclic compounds described above are conventional methods (Alan R. Katritzky, and Charles W. Rees; Comprehensive Heterocyclic Chemistry, Vol. 2, Vol. 3, Vol. 4, Vol. 5 or Vol. 6), or a heterocyclic carboxylate derivative or a heterocyclic methane derivative. To prepare compound (14), wherein Q is an oxazol-4-yl group or a thiazol-4-yl group, the carboxylic acid amide or thioamide is reacted with 1,3-dichloro-2-propanone.

Examples of compounds of the invention are shown in Tables 1-14 below. Each abbreviation in these tables refers to the meaning below.

Me: methyl group, Et: ethyl group, Pr: propyl group, Bu: butyl group, Pen: pentyl group, Hex: hexyl group, Hep: heptyl group, Oct: octyl group, Non: nonyl group, Dec: decyl group, Ph: Phenyl group, n: normal, i: iso, sec: secondary, t: tertiary, c: cyclo

When the compounds of the present invention are used as general insecticides, they are mixed with suitable carriers such as clay, talc, bentonite, diatomaceous earth or white carbon, or water, alcohols (e.g. isopropanol, butanol, benzyl alcohol, furfuryl alcohol), Aromatic hydrocarbons (eg toluene, xylene), ethers (eg anisole), ketones (eg cyclohexanone, isophorone), esters (eg butyl acetate), acid amides (eg N-methylpyrrolidone) Or mixed with halogenated hydrocarbons (e.g. chlorobenzene) and optionally added and compounded with other additives such as surfactants, emulsifiers, dispersants, penetrants, diffusing agents, thickeners, antifreeze agents, antifreeze agents and stabilizers, It is formulated into a dosage form for practical use such as an emulsion, a hydrating agent, a dry floorable, a floorable, a powder and a granule.

When the compound of the present invention is used as a pesticide, it is mixed with other herbicides, various insecticides, acaricides, nematicides, fungicides, plant growth regulators, synergists, fertilizers and soil improvers to make practical preparations or sprays. Use practically.

In particular, when used in combination with the compound of the present invention and other pesticides or plant hormones, it is possible to reduce the amount of pesticides used, thereby reducing the processing cost, and various mixed pesticides have a synergistic effect, thereby exhibiting higher insecticidal action and expanding the insecticide spectrum. There are advantages to it. If necessary, the compound of the present invention may be used in combination with many known pesticides. As an example of the pesticide which can be used together with the compound of this invention, the compound described in the "Pesticide Handbook (1994)" is mentioned.

The amount of the compound of the present invention varies depending on the place of application, the time of application, the method of application, cultivated crops, and the like, and is generally about 0.005 kg to 50 kg per hectare (ha) in terms of an effective amount.

Hereinafter, although the formulation example containing the compound of this invention is described, these formulation examples do not limit the scope of the present invention. "Parts" in the formulations below are "parts by weight".

[Hydrating]

5-80 parts of the compound of the present invention

10 to 85 parts of a solid carrier

1-10 parts of surfactant

Others 1-5

Others include, for example, anti-caking agents.

[Emulsifier]

1-30 parts of the compound of the present invention

30 to 95 parts of liquid carrier

5-15 parts of surfactant

[Floorable]

5-70 parts of a compound of the present invention

15 to 65 parts of liquid carrier

5-12 parts of surfactant

Others 5-30

Others include cryoprotectants and thickeners.

[Dryable Flooring Agent (Granular Hydrating Agent)]

20 to 90 parts of the compound of the present invention

10 to 60 parts of solid carrier

1-20 parts of surfactant

[Participation]

0.1 to 10 parts of the compound of the present invention

90 to 99.99 parts of a solid carrier

Others 1-5

[Powder]

0.01-30 parts of the compound of the present invention

Solid carrier 67 to 99.5 parts

Other 0-3

When the compound of the present invention is used as an aquatic biofouling agent, it may be formulated into various formulations applicable to various purposes such as paints, solutions, emulsions, pellets or flakes. Depending on the place of application, purpose and form, these preparations can be used by conventional methods such as, for example, application, spraying, dipping, addition in water or installation in water. Any conventional method may be used to produce such paints, solutions, emulsions, and the like.

In addition to the method of using the compound of the present invention and the above-mentioned formulations, for example, the compound of the present invention may be used when the compound of the present invention is blended in the manufacturing process of a rope for fishing nets or a fiber material to impart adhesion to aquatic organisms.

The aquatic biofouling agent according to the present invention may be used alone or in combination with other aquatic biofouling agents.

When the aquatic organisms antifouling agent of the present invention is used in the form of an antifouling paint, for example, a coating agent may be mixed with the compound of the present invention to prepare a paint. Film forming agents include oily varnishes, synthetic resins, synthetic rubbers, and the like. If necessary, solvents, pigments and the like can be added to the paint. The maximum concentration of the compound of the present invention is not particularly limited so long as the paint produced when forming the paint can form a coating, but it is 1 to 50% by weight, preferably 5 to 20% by weight, based on the weight of the antifouling paint. to be.

When the aquatic organisms antifouling agents of the present invention are used, e. Examples of the film forming agent include synthetic resins, synthetic rubbers, and soft resins. Examples of the solvent include xylene, toluene, cumene, methyl ethyl ketone, methyl isobutyl ketone, acetone and the like. As needed, you may add additives, such as a plasticizer, to a solution. The maximum concentration of the compound of the present invention is not particularly limited as long as the compound dissolves to form a solution when preparing the solution, but it is 1 to 50% by weight, preferably 5 to 30% by weight, based on the weight of the solution.

When the aquatic antifouling agent of the present invention is used in the form of an emulsion, a surfactant is added to the compound of the present invention to prepare a required emulsion according to a conventional general emulsion preparation method. The kind of surfactant used in this case is not specifically limited. As long as the compound emulsifies to produce an emulsion when preparing the emulsion, the uppermost concentration of the compound of the present invention is not particularly limited but is 1 to 50% by weight, preferably 5 to 30% by weight, based on the weight of the emulsion.

When the aquatic antifouling agents of the invention are used in pellet or flake form, for example, the constituents of the compounds of the invention and optionally plasticizers, surfactants and others are added to solid hydrophilic resin bases such as polyethylene glycol in solid form at room temperature. The resulting mixture is molded into pellets or flakes by melt molding or compression molding. The maximum concentration of the compound is not particularly limited as long as the compound can be formed into pellets or flakes when preparing the pellets or flakes, but is 25 to 90% by weight, preferably 30 to 90% by weight of the pellets or flakes. %to be.

The present invention will be described in detail by the following Synthesis Examples, Formulation Examples and Test Examples, which do not limit the scope of the present invention.

Synthesis Example 1

2- {3- (2,6-difluorophenyl) pyrazol-1-yl} -3- (1-methyl-3,5-dichloropyrazol-4-yl) -3-hydroxyacrylonitrile Synthesis of (Compound No. I-40):

1) 3.0 g of 3- (2,6-difluorophenyl) pyrazole was dissolved in 20 ml of acetonitrile, and 2.52 g of chloroacetonitrile and 4.61 g of potassium carbonate were added at room temperature and heated at reflux for 5 hours. Acetonitrile was distilled off under reduced pressure and ethyl acetate was added to the residue, which was then washed with a small amount of water. The organic layer was dried over sodium sulfate and the solvent was distilled off under reduced pressure. The remaining product was recrystallized from a mixed solvent of isopropyl ether and diethyl ether to obtain 1.74 g of 1-cyanomethyl-3- (2,6-difluorophenyl) pyrazole.

2) A solution of 0.5 g of 1-cyanomethyl-3- (2,6-difluorophenyl) pyrazole in 10 ml of THF was added dropwise to a suspension of 0.15 g of 55% sodium hydride in 10 ml of THF at 50 ° C. After the obtained product was stirred for 30 minutes, a solution of 0.67 g of 1- (1-methyl-3,5-dichloropyrazole-4-carbonyl) pyrazole in 10 ml of THF was added dropwise at 50 ° C. overnight at room temperature. Stirred. The reaction mixture was poured into water, extracted with ethyl acetate and washed with a small amount of water. The resulting product was dried over sodium sulfate and the solvent was distilled off under reduced pressure. The remaining product was recrystallized from a mixed solvent of isopropyl ether / ethyl acetate = 3/1 to give 2- {3- (2,6-difluorophenyl) pyrazol-1-yl} -3- (1-methyl- 0.52 g of 3,5-dichloropyrazol-4-yl) -3-hydroxyacrylonitrile was obtained.

Synthesis Example 2

3- (1-methyl-3,5-dichloropyrazol-4-yl) -2- (2-phenylthiazol-4-yl) -3-hydroxyacrylonitrile (Compound No. No. II-1 Synthesis of):

1) 2.33 g of thiobenzamide was dissolved in 20 ml of anhydrous methanol, and 2.16 g of 1,3-dichloroacetone was added thereto at room temperature and heated at reflux for 1 hour. The solvent was distilled off under reduced pressure, and iced water was added to the obtained product, which was then neutralized with an aqueous sodium hydrogen carbonate solution. The obtained product was extracted with ethyl acetate, washed with saturated brine, dried over sodium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 2.03 g of 4-chloromethyl-2-phenylthiazole from the eluted fraction with chloroform / n-hexane = 1/2.

2) 1.39 g of 4-chloromethyl-2-phenylthiazole was dissolved in 10 ml of acetonitrile, and 0.65 g of potassium cyanide and 0.05 g of dibenzo-18-crown-6-ether were added thereto at room temperature, followed by 10 at reflux. Heated for hours. After the temperature was brought to room temperature, ethyl acetate was added to the obtained mixture, and the insoluble solid was filtered off. The obtained ethyl acetate solution was washed with saturated brine and water, dried over sodium sulfate, and then the solvent was distilled off under reduced pressure. The remaining product was purified by silica gel column chromatography to obtain 0.98 g of 4-cyanomethyl-2-phenylthiazole from the eluted fractions with chloroform.

3) 0.72 g of 4-cyanomethyl-2-phenylthiazole was dissolved in 10 ml of anhydrous THF, and 4.6 ml of n-butyl lithium (1.56 M hexane solution) was added dropwise at -60 DEG C or lower in argon atmosphere. . The resulting product was stirred at -60 占 폚 for 20 minutes, and then a solution of 0.84 g of 1-methyl-3,5-dichloropyrazole-4-carbonyl chloride in 3 ml of dry THF was added dropwise at -60 占 폚. It was. The resulting product was then slowly heated and stirred at room temperature for 4 hours. The reaction mixture was poured into iced water, acidified with diluted hydrochloric acid, extracted with ethyl acetate, and washed with saturated brine. The obtained product was dried over sodium sulfate, and then the solvent was distilled off under reduced pressure. The desired product was purified by silica gel column chromatography to obtain the desired product from the elution fraction with chloroform. The obtained product was recrystallized and washed with diethyl ether to give 3- (1-methyl-3,5-dichloropyrazol-4-yl) -2- (2-phenylthiazol-4-yl) -3-hydroxy 0.86 g of acrylonitrile was obtained.

Synthesis Example 3

3- (1-methyl-3-trifluoromethyl-5-chloropyrazol-4-yl) -2- (4-tert-butylthiazol-2-yl) -3-pivaloyloxyacrylonitrile Synthesis of (Compound No. III-6, III-15):

0.5 g of 3- (1-methyl-3-trifluoromethyl-5-chloropyrazol-4-yl) -2- (4-tert-butylthiazol-2-yl) -3-hydroxyacrylonitrile And 0.14 g of triethylamine were added to 15 ml of THF at room temperature, followed by stirring to obtain a uniform solution. 0.16 g of pivaloyl chloride was added dropwise to the solution under ice-cooling, and then the mixture was slowly heated and stirred at room temperature for 8 hours. The reaction mixture was poured into ice water, extracted with ethyl acetate and washed three times with saturated brine. After drying over sodium sulfate, the obtained product was passed through a short column filled with silica gel. The solvent was distilled off under reduced pressure and the remaining product was subjected to silica gel thin layer chromatography treatment (developing solvent: chloroform) to give 3- (1-methyl-3-trifluoromethyl-5-chloropyrazol-4-yl)- 0.16 g of 2- (4-tert-butylthiazol-2-yl) -3-pivaloyloxyacrylonitrile (III-6) and 0.35 g of its geometric isomer (III-15) were obtained.

Compound no. III-6:

Compound no. III-15:

[Reference Example]

Synthesis of 1-methyl-3-trifluoromethyl-5-chloropyrazole-4-carboxylic acid:

1) 21.53 g of phosphorus oxychloride was added dropwise to 4.72 g of DMF at 10 ° C. or lower, the reaction mixture was allowed to come to room temperature, and the reaction mixture was stirred for 1 hour, followed by 1-methyl-3-trifluoromethyl 10.71 g of -5-pyrazolone was added. The resulting mixture was heated to 110 ° C. and stirred for 7 hours. After standing at 70 ° C., the reaction mixture was poured into ice water, and an aqueous sodium hydroxide solution was added thereto to bring the pH of the reaction mixture to about 4. The precipitated crystals were collected by filtration and dried to obtain 10.55 g of 1-methyl-3-trifluoromethyl-5-chloropyrazole-4-carboaldehyde.

2) 8.88 g of 1-methyl-3-2- (tert-trifluoromethyl-5-chloropyrazole-4-carboaldehyde and 7.24 g of potassium permanganate were added to an aqueous solution of 0.23 g of potassium hydroxide in 85 ml of water at room temperature. The mixture was stirred and heated to 60 ° C., and the resulting mixture was stirred for 2 hours The temperature of the reaction mixture was returned to room temperature and the solids were removed by filtration The resulting filtrate was acidified with aqueous hydrochloric acid solution and the precipitated crystals were filtered The crystals thus obtained were added to 150 ml of chloroform, heated under reflux, and the insoluble solids were removed by filtration under hot conditions .. Chloroform was distilled off under reduced pressure to remove 1-methyl-3-. 6.24 g of trifluoromethyl-5-chloropyrazole-4-carboxylic acid was obtained.

Synthesis Example 4

2- (2-tert-butylthiazol-4-yl) -3- (2-methyl-4-trifluoromethylthiazol-5-yl) -3-benzoyloxyacrylonitrile (Compound No.II- Compound of 75):

The above compound was synthesized in the same manner as above. (Viscous liquid, E-Z mixture).

Synthesis Example 5

2- (4-trifluoromethylphenyl) -3- (1-methyl-3,5-dichloropyrazol-4-yl) -3- (1-methyl-3,5-dichloropyrazole-4-carbonyl Synthesis of oxy) acrylonitrile (Compound No. IV-5):

1.0 g of 4- (trifluoromethyl) phenylacetonitrile and 2.31 g of 1-methyl-3,5-dichloropyrazole-4-carbonyl chloride are dissolved in 30 ml of dry THF, and 0.61 g of potassium t-butoxide is added thereto. Was added at room temperature. After heating, the obtained product was heated under reflux for 3 hours, and then 0.61 g of potassium t-butoxide was added thereto, and the mixture was heated to reflux for 2 hours. THF was distilled off under reduced pressure, water was added to the obtained product, followed by extraction with ethyl acetate. The resulting organic layer was washed with diluted aqueous sodium hydroxide solution, washed with water, dried over sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain n-hexane: ethyl acetate = 2: 1 3- (1-methyl-3,5-dichloropyrazol-4-yl) -2- (4-trifluoromethylphenyl) -3- (1-methyl-3,5-dichloropyrazole from elution fractions by 1.92 g of 4-carbonyloxy) acrylonitrile were obtained.

Synthesis Example 6

Synthesis of 2- (4-tert-butylphenyl) -3- (1-methyl-3,5-dichloropyrazol-4-yl) -3-hydroxyacrylonitrile (Compound IV-18):

0.22 g of dibenzo-18-crown-6-ether and 1.57 g of sodium cyanide were suspended in 20 ml of DMSO, to which 5.00 g of 4-tert-butylbenzyl bromide was added dropwise while cooling with water. After stirring overnight at room temperature, the obtained mixture was further stirred at 50 ° C. for 5 hours. After standing at room temperature, water was added thereto, followed by extraction with ether. The organic layer was washed with water, dried over sodium sulfate and the solvent was removed by evaporation under reduced pressure. The remaining product was removed by silica gel column chromatography to obtain 1.19 g of 4-tert-butylphenylacetonitrile from an eluted fraction with n-hexane: ethyl acetate = 5: 1.

1.00 g of 4-tert-butylphenylacetonitrile and 1.23 g of 1-methyl-3,5-dichloropyrazole-4-carbonyl chloride are dissolved in 20 ml of THF, and 1.01 g of potassium t-butoxide is added thereto under ice-cooling. It was. The resulting mixture was stirred overnight at room temperature, after which water was added, acidified with diluted hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The remaining product was dissolved in a mixed solvent of 10 ml of water and 10 ml of dioxane, and 0.38 g of potassium hydroxide was added thereto and heated under reflux for 4 hours. After standing at room temperature it was acidified with dilute hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and dried over sodium sulfate, and then the solvent was distilled off under reduced pressure. By removing the remaining product by silica gel column chromatography, 2- (4-tert-butylphenyl) -3- (1-methyl-3,5- from the elution fraction with n-hexane: ethyl acetate = 2: 1) 0.64 g of dichloropyrazol-4-yl) -3-hydroxyacrylonitrile was obtained.

Synthesis Example 7

2- (4-tert-butylphenyl) -3- (1-methyl-3-trifluoromethyl-5-chloropyrazol-4-yl) -3-pivaloyloxyacrylonitrile (Compound IV-24 Synthesis of):

The above compounds were synthesized in the same manner as above (viscous liquid).

Synthesis Example 8

Synthesis of 2- (4-tert-butylphenyl) -3- (3,5-dichloro-1-methylpyrazol-4-yl) -3-methoxycarbonyloxyacrylonitrile (Compound IV-36):

The above compounds were synthesized in the same manner as above (glassy, E-Z mixture).

Synthesis Example 9

2- {2-tert-butyloxazol-4-yl} -3- (3,5-dichloro-1-methyl-pyrazol-4-yl) -3-hydroxyacrylonitrile (Compound V-40) Synthesis of:

1) 25 g of pivalic acid amide and 25 g of 1,3-dichloro-2-propanone were mixed and heated in an oil bath at 135 ° C. for 2.5 hours. After cooling with ice, an aqueous sodium hydroxide solution was added to the mixture to make it alkaline. The resulting product was extracted with ethyl acetate, washed with water, dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The remaining product was purified by column chromatography (silica gel; ethyl acetate: n-hexane = 1: 8) to give 17.5 g of 2-tert-butyl-4-chloromethyloxazole.

2) Weigh 6.2 g of sodium cyanide and add 50 ml of dimethyl sulfoxide to it, followed by dropwise addition of 16.9 g of dimethyl sulfoxide solution of 2-tert-butyl-4-chloromethyloxazole, followed by oil bath at 65 ° C. Heated with stirring for 1 hour. After cooling the obtained product to room temperature, 150 ml of diluted sodium hydroxide aqueous solution was added, and it extracted with toluene. The organic layer was washed thoroughly with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 14.8 g of 2-tert-butyl-4-cyanomethyloxazole.

3) 2.87 g of potassium t-butoxide was suspended in 20 ml of THF, and 2.00 g of 2-tert-butyl-4-cyanomethyloxazole and 3,5-dichloro-1-methylpyrazole-4-carb were dissolved in 20 ml of THF. A solution of 2.37 g of carbonyl chloride was added dropwise under ice-cooling, followed by stirring overnight at room temperature. The reaction mixture was poured into iced water, extracted with ethyl acetate and washed with a small amount of water. The obtained product was dried over anhydrous sodium sulfate and the solvent was removed by evaporation under reduced pressure. The remaining product was purified by column chromatography (silica gel; n-hexane: ethyl acetate = 4: 1) to obtain 3.26 g of the target compound.

Synthesis Example 10

2- (2-tert-butyloxazol-4-yl) -3- (5-chloro-1-methyl-3-trifluoromethylpyrazol-4-yl) -3-ethoxymethoxyacrylonitrile Synthesis of (Compound V-44):

2- {2-tert-butyloxazol-4-yl} -3- (5-chloro-3-trifluoromethyl-1-methyl-pyrazol-4-yl) -3-hydroxyacrylonitrile 0.6 g was dissolved in 5 ml of THF, and 0.07 g of 60% sodium hydride was added thereto under ice cooling, followed by stirring at room temperature for 15 minutes. 0.17 g of ethoxymethyl chloride was added thereto and stirred at room temperature for 6 days. The reaction mixture was poured into iced water, extracted with ethyl acetate and washed with saturated brine. The obtained product was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained remaining product was purified by silica gel thin layer chromatography (ethyl acetate: n-hexane = 1: 4) to obtain 0.1 g of the target glassy compound.

Synthesis Example 11

Synthesis of ethyl 2-phenyl-3- (3,5-dichloro-1-methylpyrazol-4-yl) -3-hydroxyacrylate (Compound No. IV-91):

8.2 g (50 mmol) of ethyl phenylacetate and 10.7 g (50 mmol) of 3,5-dichloro-1-methylpyrazole-4-carboxylic acid chloride were dissolved in 100 ml of anhydrous tetrahydropyran and 14 g (125 mmol) of potassium tert-butoxide at room temperature. The reaction mixture was stirred at room temperature for 1 hour, after which 300 ml of water was added and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain the desired ethyl 2-phenyl-3- (3,5-dichloro-1-methylpyrazol-4-yl). 17g of -3-hydroxyacrylates were obtained.

Synthesis Example 12

Synthesis of 1- (3,5-dichloro-1-methylpyrazol-4-yl) -2-phenyl-2-bromoethanone (Compound No. IV-90):

1) Ethyl 2-phenyl-3- (3,5-dichloro-1-methylpyrazol-4-yl) -3-hydroxyacrylate 17 g (50 mmol) in 50 ml of 6 N HCl and 250 ml of 1,4-dioxane Dissolved in and heated to reflux for 15 minutes. The reaction mixture was poured into 500 ml of ice water, and the precipitated crystals were collected by filtration to obtain 8 g of the desired 1- (3,5-dichloro-1-methylpyrazol-4-yl) -2-phenylethanone as white crystals. . m.p .: 94-96 ° C

2) 5.38 g (20 mmol) of 1- (3,5-dichloro-1-methylpyrazol-4-yl) -2-phenylethane was dissolved in 50 ml of chloroform, stirred at room temperature for 1 hour, and the solvent was distilled off under reduced pressure. By removing, the target 1- (3,5-dichloro-1-methylpyrazol-4-yl) -2-phenyl-2-bromoethanone was obtained as white crystals. m.p .: 74.5-75.5 ° C

Synthesis Example 13

Synthesis of 1- (3,5-dichloro-1-methylpyrazol-4-yl) -1-pivaloyloxy-2-phenyl-2-bromoethylene (Compound No. IV-92):

0.55 g (1.58 mmol) of 1- (3,5-dichloro-1-methylpyrazol-4-yl) -2-phenyl-bromoethane and 0.18 g (1.74 mmol) of triethylamine were added to 4 ml of anhydrous tetrahydrofuran. It was dissolved and 0.19 g (1.58 mmol) of pivalic acid chloride was added thereto at room temperature. The reaction mixture was stirred at room temperature for 16 hours, after which 10 ml of water was added and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain the desired 1- (3,5-dichloro-1-methylpyrazol-4-yl) -1-pivaloyloxy-2-phenyl-2- 0.23 g of bromoethylene was obtained as a colorless liquid (EZ mixture).

Synthesis Example 14

1- (3,5-Dichloro-1-methylpyrazol-4-yl) -2- {2- (1-methylcyclohexane-1-yl) -thiazol-4-yl} -2-diethylforce Synthesis of Phonoethanone (Compound No. II-156):

1) 4.15 g (18.1 mmol) of 2- (1-methyl-cyclohexane-1-yl) -4-chloromethylthiazole and 3.32 g (20 mmol) of trimethyl phosphite were mixed and heated under reflux for 16 hours. 4.63 g of the desired diethyl {2- (1-methylcyclohexane-1-yl) -thiazol-4-yl} methylphosphonate by cooling the reaction mixture to room temperature and purifying by silica gel column chromatography. Was obtained as a colorless liquid.

2) 0.85 g (4 mmol) of 3,5-dichloro-1-methylpyrazole-4-carboxylic acid chloride and diethyl {2- (1-methylcyclohexane-1-yl) -thiazol-4-yl} methylforce 1.32 g (4 mmol) of fonate was dissolved in 15 ml of anhydrous tetrahydrofuran and 1.12 g (10 mmol) of potassium t-butoxide were added at room temperature. The reaction mixture was stirred at room temperature for 1 hour, and 20 ml of water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain the desired 1- (3,5-dichloro-1-methylpyrazol-4-yl) -2- {2- (1-methylcyclohexane-1 0.4 g of -yl) -thiazol-4-yl} -2-diethylphosphoethanone was obtained.

Synthesis Example 15

Allyl 2- {3- (2,6-difluorophenyl) pyrazol-1-yl} -3- (5-chloro-1-methyl-3-trifluoromethylpyrazol-4-yl) -3 Synthesis of hydroxyacrylate (Compound No. I-133):

1) Potassium carbonate (1.53 g) was added to an acetonitrile (10 mL) solution of 3- (2,6-difluorophenyl) pyrazole (1 g) and allyl 2-bromoacetate (1.49 g) and refluxed for 3 hours. . The resulting product was extracted with ethyl acetate and diluted hydrochloric acid was added at room temperature. The organic layer was dried over anhydrous magnesium sulfate and concentrated, and then the obtained concentrate was purified by silica gel column chromatography (chloroform) to allyl 2- {3- (2,6-difluorophenyl) pyrazole-1- Japanese acetate (1.5 g) was obtained.

2) allyl 2- {3- (2,6-difluorophenyl) pyrazol-1-yl} acetate (0.5 g) and 5-chloro-1-methyl-3-trifluoromethylpyrazole-4- Potassium butoxide (0.5 g) was added to a THF (10 mL) solution of carbonyl chloride (0.44 g) at 0 ° C. and stirred for 5 minutes. Water (5 ml) was added thereto, followed by extraction with dilute hydrochloric acid and ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated, and then the obtained concentrate was purified by silica gel column chromatography (chloroform) to obtain Compound No. I-133 (0.89 g) was obtained.

Synthesis Example 16

2-bromo-2- {3- (2,6-difluorophenyl) pyrazol-1-yl} -1- (5-chloro-1-methyl-3-trifluoromethylpyrazole-4- Synthesis of l) -1-hydroxyethylene (Compound No. I-134):

1) Formic acid (60 mg) was added to a THF (1 mL) solution of palladium acetate (7 mg) and triphenylphosphine (17 mg) and stirred at room temperature for 5 minutes in a nitrogen atmosphere. A THF (5 mL) solution of compound I-133 (0.32 g) was added thereto, and the mixture was refluxed for 1 hour. The reaction mixture was left at room temperature and then concentrated, and the resulting concentrate was purified by silica gel column chromatography (chloroform) and then recrystallized (chloroform-diisopropyl ether) to give 2- {3- (2,6-di Fluorophenyl) pyrazol-1-yl} -3- (5-chloro-1-methyl-3-trifluoromethylpyrazol-4-yl) ethan-1-one (0.1 g) was obtained. m.p .: 152-154 ° C

2) THF solution (0.27 mL) of 1M lithium hexamethyldisilazide was added with 2- {3- (2,6-difluorophenyl) pyrazol-1-yl} -3- (5-chloro-1-methyl 3-trifluoromethylpyrazol-4-yl) ethan-1-one (0.1 g) was added to a THF solution at -78 ° C and stirred in a nitrogen atmosphere at the same temperature. A THF (2 mL) solution of carbon tetrabromide (0.098 g) was added to the resulting solution, and the temperature was gradually raised to room temperature. Water (1 mL) was added thereto, followed by extraction with dilute hydrochloric acid and ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized from chloroform-diethyl ether to give the titled compound No. I-134 (0.062 g) was obtained. m.p .: 123-125 ℃

Synthesis Example 17

2-bromo-2- {3- (2,6-difluorophenyl) pyrazol-1-yl} -1- (5-chloro-1-methyl-3-trifluoromethylpyrazole-4- Synthesis of I) -1-pivaloyloxyethylene (Compound No. I-135):

Compound no. To a solution of I-134 (0.47 g) at 0 ° C. in chloroform (25 mL) was added triethylamine (0.3 g) and pivalic acid chloride (0.23 g) in this order and stirred at room temperature for 1 hour. The obtained product was extracted with water and chloroform. The organic layer was dried over anhydrous magnesium sulfate, concentrated and purified by silica gel column chromatography (chloroform) to obtain Compound No. I-135 (0.4 g) was obtained.

Various compounds of the present invention were prepared according to the above reaction scheme or examples, but the structures, melting points, and the like of these compounds are shown in Tables 15 to 19 below. Unless otherwise specified, the compounds in these tables are in the form of mixtures of E and Z forms. Their abbreviations have the same meaning as mentioned above.

[Example]

Hereinafter, although the formulation example of the pesticide containing the compound of this invention as an active ingredient is shown below, these do not limit the scope of the present invention. In each formulation example below, "part" is "part by weight".

Preparation Example 1 Hydration:

Compound No. of the present invention I-1 50

Zeeklite PFP

(Brand name of kaolin clay made by Zeeklite Mining Industries) 43 parts

Solpol 5050 (trade name of anionic surfactants manufactured by Toho Chemical) 2 parts

Runox 1000C (trade name of anionic surfactants manufactured by Toho Chemical)

                                                                    Part Three

Carplex # 80

(Antifreeze, brand name of white carbon made by Shionogi Pharmaceutical)

Each of the above components were mixed homogeneously and powdered to prepare a hydrating agent.

Preparation Example 2 Emulsifier

Compound No. of the present invention I-1 Part 3

Methylnaphthalene 76 parts

Isophoron part 15

Solpole 3005X (Nonionic Surfactant and Anion, manufactured by Toho Chemical, Inc.)

Mixture of surfactant, trade name) 6 parts

Each of the above components were mixed homogeneously to prepare an emulsion.

[Example 3] Floorable agent:

Compound No. of the present invention I-1 35

8 parts of Agrisol S-711 (nonionic surfactant made by Kao, trade name)

Runox 1000C (trade name of anionic surfactants manufactured by Toho Chemical) 0.5 part

20 parts of aqueous solution of 1% Rhodopol (a thickener manufactured by Rhone-Poulenc, trade name)

Ethylene Glycol (Freeze Inhibitor) 8 parts

28.5 parts of water

The above components were mixed homogeneously to prepare a flooring agent.

Preparation Example 4 Granular Hydrating Agent (Dryable Flooring Agent):

Compound No. of the present invention I-1 Part 75

Isoban No.1

(Trade name of anionic surfactants manufactured by Kuraray Isoprene Chemical) 10 parts

Vanilex N

(Brand name of anionic surfactant made by Sanyo Kokusaku Pulp)

Carplex # 80

(Brand name of white carbon made in Shinogi Pharmaceutical company) ten parts

The components were mixed homogeneously and finely powdered to prepare a dry floorable.

EXAMPLE 5 Preparation

Compound No. of the present invention I-1 0.1

Bentonite Part 55.0

Talc 44.9

The ingredients were homogeneously mixed and powdered, to which a small amount of water was added, stirred, mixed and kneaded. The obtained mixed rice product was granulated using an extrusion granulator and dried, and granules were obtained.

Preparation Example 6 Powder

Compound No. of the present invention I-1 Part 3.0

Carplex # 80

(Brand name of white carbon by Shinogi Pharmaceutical company) 0.5 part

Clay part 95

1.5 parts of diisopropyl phosphate

The ingredients were homogeneously mixed and powdered to prepare a powder.

At the time of use, a hydrating agent, an emulsifying agent, a floorable agent, and a dry floorable agent are diluted 50-20000 times with water, and it converts into an effective ingredient, and applies it in the quantity of 0.005-50 kg / ha.

EMBODIMENT OF THE INVENTION Hereinafter, although the preparation example of the aquatic organisms adhesion inhibitor of this invention is described, these do not limit the scope of the present invention.

[Example 7]

Compound No. of the present invention II-2 Part 8

VYHH (vinyl synthetic resin made by UCC) 7 parts

Rosin Part 7

Tricresyl phosphate part 3

Talc 20

15 parts of barium sulfate

10 parts red iron oxide

Xylene Part 20

Methyl isobutyl ketone 10 parts

The above components were mixed homogeneously to prepare an aquatic adhesion inhibitor of the present invention. This formulation can be used as a paint.

[Example 8]

Compound No. of the present invention II-2 Part 5

13 parts of CR-10 (Asahi Denka Co., Ltd.)

20 parts of zinc powder

Talc 20

Plasticizer Part 2

10 parts red iron oxide

Xylene 30

The above components were mixed homogeneously to prepare an aquatic adhesion inhibitor of the present invention. This formulation can be used as a paint.

[Example 9]

Compound No. of the present invention II-2 Part 8

VYHH (vinyl synthetic resin made by UCC) 7 parts

Rosin Part 7

Tricresyl phosphate part 3

Talc 20

15 parts of barium sulfate

10 parts red iron oxide

Xylene Part 20

Methyl isobutyl ketone 10 parts

The above components were mixed homogeneously to prepare an aquatic adhesion inhibitor of the present invention. This formulation can be used as a paint.

[Example 10]

Compound No. of the present invention II-2 Part 5

13 parts of CR-10 (Asahi Denka Co., Ltd.)

20 parts of zinc powder

Talc 20

Plasticizer Part 2

10 parts red iron oxide

Xylene 30

The above components were mixed homogeneously to prepare an aquatic adhesion inhibitor of the present invention. This formulation can be used as a paint.

[Test Example]

Hereinafter, the usefulness as a pesticide of the compound of this invention in each test example below is demonstrated.

Test Example 1: Insecticidal test on Brown rice myeolgu (Nilaparvata lugens Stal)

A 500 ppm solution of the compound was prepared by diluting the 5% emulsifier (or 25% hydrating agent) of the compound of the present invention with water containing a diffusing agent.

The solution was sufficiently applied to the stems and leaves of rice in pots of 1 / 20,000 ar. The applied chemicals were dried in air and each port was covered with a cylindrical cover. Loose and put my two young chunggi larvae of brown rice myeolgu 10 (Nilaparvata lugens) in each port. After closing the lid, each pot was stored in a constant temperature room, and after six days, the insects of each pot were observed, and the mortality was calculated according to the following equation. Each compound was tested in the manner for port 2 group.

% Mortality = [number of worms killed / (number of worms killed + number of live worms)] × 100

In this test, the following compounds showed a mortality of at least 80%.

Test Example 2: Insecticidal test on Nephotettix cincticeps U hler

Stem and leaves of the plant in a 500ppm emulsion of the compound of the present invention was immersed for about 10 seconds and then placed in a glass cylinder, where the adult of green rice larvae ( Nephotettix cincticeps ) resistant to organic insecticides Released. Each glass cylinder was covered with a perforated cover and stored in a constant temperature chamber at 25 ° C. After 6 days, the insects in each cylinder were observed, and the mortality of the insects was determined according to the same formula as in Test Example 1.

Each compound was tested in the manner for cylinder 2 group. In this test, the following compounds had a mortality rate of 80% or more.

Test Example 3: Insecticidal test on green peach aphid ( Myzus persicae Sulzer )

The soaked filter paper was placed in each laboratory glass dish with an inner diameter of 3 cm and cabbage leaves having the same diameter as the dish were placed on the filter paper. Four apterous adult females of green peach aphid ( Myzus persicae ) were placed on cabbage leaves and the next day a pesticide sample (2.5 mg / cm ² ) was sprayed onto the dish using a Rotaring sprinkler. Pesticide solutions are prepared by diluting a 5% emulsifier (or 25% hydrating agent) of a compound of the present invention to 500 ppm with water containing a diffusing agent. After 6 days, the insects in each cylinder were observed, and the lethality (larvae and adults) of the insects was determined according to the following equation. Each compound was tested in the manner for two groups of dishes.

% Mortality = [number of worms killed / (number of worms killed + number of live worms)] × 100

In this test, 80% or more of the following compounds showed mortality.

Test Example 4: Insecticidal test on diamondback moth ( Plutella xylostella Linne )

After immersing cabbage leaves in a 500 ppm aqueous emulsion of the compound of the present invention for about 10 seconds and drying in air, the treated leaves are placed in a laboratory dish, and the second largest larvae of diamond-patterned moths ( Plutella xylostella ) on the back 10 Marie was released into each dish. Each dish was covered with a perforated cover and stored in a thermostat at 25 ° C. After 6 days, the insects in each dish were observed, and the mortality of the insects was determined according to the same formula as in Test Example 1. Each compound was tested in the manner for two groups of dishes.

In this test, the following compounds had a mortality rate of 80% or more.

Insecticidal test for the gourd leaf beetle (Aulacophora femoralis Motschulsky): Test Example 5

A 500 ppm solution of the compound was prepared by diluting the 5% emulsifier (or 25% hydrating agent) of the compound of the present invention with water containing a diffusing agent. Cucumber leaves were immersed in the pesticide bath for about 10 seconds, dried in the air and placed in a laboratory dish. Ten larval insect larvae of Gourd leaf beetle ( Aulacophora femoralis ) were released into each dish, covered with a lid, and stored in a constant temperature room at 25 ° C. After 6 days, the worms of each dish were observed, and the mortality was determined according to the same formula as in Test Example 1. Each compound was tested in the manner for two groups of dishes.

In this test, the following compounds showed a mortality of 100%.

Test Example 6: Tick test for two-spotted spider mite ( Tetranychus urticae Koch )

Gangnam bean leaves were punched into a disc shape of 3 cm diameter using a punch and placed on a wet filter paper in a 7 cm diameter styrol cup. Ten larvae of two-spotted spider mite ( Tetranychus urticae ) were placed on each leaf. Diluting the 5% emulsifier (or 25% hydrating agent) of the compound of the present invention with water containing a diffusing agent to prepare a 500 ppm solution of the compound, using a rotary sprinkler sprayed each solution in an amount of 2 ml per cup Each cup was then stored in a constant temperature room at 25 ° C. After 6 days, the ticks in each cup were observed to determine the mortality of the ticks according to the same formula as in Test Example 1. Each compound was tested in the manner for cup 2 group. In this test, the following compounds had a mortality rate of 80% or more.

Test Example 7: Control test for leaf rust (brown rust) ( Puccinia recondita ex Desmaziere)

A pesticide solution of an emulsifier of the compound of the present invention diluted to 500 ppm with water was sprayed on a wheat tree (Norin No. 61) grown from 1.5 to 2.0 leaves in a pot of 5.5 cm in diameter with a spray gun at an amount of 20 ml per port. .

The next day, a spore suspension (2 × 10 ⁵ pieces / ml) of leaf rust (brown rust) ( Puccinia recondita ) was sprayed onto the plant in the pot and left overnight in an inoculation box of 25 ° C. and 95% humidity. Subsequently, each pot was placed in a greenhouse, and after 7 days of inoculation, the percentages of infection and spots generated for the inoculated leaves were obtained, and control values were obtained according to the following equation.

Control value = [1- (Infection and spot area in the treatment group / Infection and spot area in the untreated group)] × 100

In this test, the following compounds showed control values of 70-100.

With the long-term use of insecticides and fungicides, some pests have recently become resistant to pesticides, which makes it difficult to eradicate them by conventional insecticides and fungicides. Moreover, some pesticides are highly toxic, do not degrade and tend to remain long term, destroying the ecosystem. Accordingly, the present invention provides novel non-toxic and non-residual insecticides and fungicides, and also provides an aquatic attachment preventing agent with little effect on the ecosystem and causing little secondary pollution.

Claims (16)

Ethylene derivatives represented by the following formula (I): In the above formula, Q is a phenyl group which may be substituted by G, a naphthyl group, or a heterocyclic group which may be substituted by R (The heterocyclic group is thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, pyrazolyl, Imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-tria Zolyl, 1,2,3,4-tetrazolyl, pyridyl, pyrimidinyl or imidazolinone); A is a phenyl group which may be substituted by W, a naphthyl group, or a heterocyclic group which may be substituted by Y (The heterocyclic group is thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, pyrazolyl, Imidazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, pyridyl, pyrimidinyl or pyrazinyl); However, when (a) Q is a thienyl group which may be substituted by R or a furyl group which may be substituted by R, A may be substituted by naphthyl group or Y heterocyclic group (the heterocyclic group may be pyrrolyl, Oxazolyl, isoxazolyl, thiazolyl, pyrazolyl, imidazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, pyrimidinyl or pyrazinyl); (b) when Q is a 2-thiazolyl group which may be substituted by R, A is a naphthyl group or a heterocyclic group which may be substituted by Y (the heterocyclic group may be thienyl, furyl, pyrrolyl, oxazolyl, iso Oxazolyl, thiazolyl, pyrazolyl, imidazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, pyridyl, pyrimidinyl or pyrazinyl); (c) When Q is a pyridyl group which may be substituted by R, A is a heterocyclic group which may be substituted by Y (The heterocyclic group may be pyrrolyl, oxazolyl, isooxazolyl, thiazolyl, pyrazolyl, already Dazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl or pyrazinyl); (d) When Q is a 1,2,3-triazolyl group which may be substituted by R, A is a naphthyl group or a heterocyclic group which may be substituted by Y (The heterocyclic group may be thienyl, furyl, pyrrolyl, Oxazolyl, isoxazolyl, thiazolyl, pyrazolyl, imidazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, pyridyl, pyrimidinyl or pyrazinyl); (e) when Q is a 1,2,4-triazolyl group which may be substituted by R, A is a heterocyclic group which may be substituted by Y (the heterocyclic group may be thienyl, furyl, pyrrolyl, oxazolyl, Isoxoxazolyl, thiazolyl, pyrazolyl, imidazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, pyrimidinyl or pyrazinyl); (f) When Q is a phenyl group which may be substituted by G, A is a heterocyclic group which may be substituted by Y (The heterocyclic group may be pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, pyrazolyl, 1, 2,3-thiadiazolyl, 1,2,3-triazolyl or pyrazinyl); (g) when Q is a naphthyl group, A is a heterocyclic group which may be substituted by Y (the heterocyclic group is thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, pyrazolyl, imidazolyl, 1 , 2,3-thiadiazolyl, 1,2,3-triazolyl, pyridyl, pyrimidinyl or pyrazinyl); B is H, C ₁ -C ₄ alkyl group, C ₁ -C ₄ haloalkyl group, C ₂ -C ₄ alkoxyalkyl group, CH ₃ OC ₂ H ₄ OCH ₂ , C ₁ -C ₄ alkyl group substituted with a phenyl group, substituted with benzoyl A phenylsulfonyl group which may be substituted by a substituted C ₁ -C ₄ alkyl group, a C ₁ -C ₄ alkylsulfonyl group, a halogen or a C ₁ -C ₄ alkyl group, -SO ₂ CF ₃ , C ₂ -C ₈ dialkylaminosulfo Nyl group, C ₃ -C ₉ dialkylaminothiocarbonyl group, C ₃ -C ₉ alkoxycarbonylalkyl group, -C (= O) T ¹ , -P (-O) T ² T ³ , alkali metal atom or NHT ⁴ T ⁵ T ⁶ is represented; Provided that when Q is a 2-thiazolyl group, B is C ₁ -C ₄ alkyl group, C ₁ -C ₄ haloalkyl group, C ₂ -C ₄ alkoxyalkyl group, CH ₃ OC ₂ H ₄ OCH ₂ , C substituted with phenyl group ₁ -C ₄ alkyl group, a substituted benzoyl C ₁ -C ₄ alkyl, C ₁ -C ₄ alkylsulfonyl group, optionally substituted by halogen or C ₁ -C ₄ alkyl good phenyl sulfonyl group, -SO ₂ CF _3, C ₂ -C ₈ dialkylaminosulfonyl group, C ₃ -C ₉ dialkylaminothiocarbonyl group, C ₃ -C ₉ alkoxycarbonylalkyl group, -C (= O) T ¹ or -P (-O) T ² T ³ E represents CN; G is a halogen atom, C ₁ -C ₁₀ alkyl group, C ₂ -C ₄ cyanoalkyl group, C ₂ -C ₆ alkenyl group, C ₁ -C ₆ haloalkyl group, C ₁ -C ₁₀ alkoxy group, C ₂ -C ₆ alkenyloxy group, C ₁ -C ₄ haloalkoxy group, C ₂ -C ₆ alkenyloxy group halo, C ₂ -C ₆ alkynyloxy group halo, C ₁ -C ₄ alkylsulfonyl group, C ₁ -C ₄ alkylsulfinyl group , C ₁ -C ₄ alkylsulfonyl group, NO ₂ , -NU ¹ U ² , methoxy group substituted by phenyl which may be substituted by halogen, C ₂ -C ₇ alkoxycarbonyl group, C ₂ -C ₄ alkylcarbonyl group, C A substituent selected from a ₃ -C ₇ dialkylaminocarbonyloxy group, a phenyl group, a phenoxy group and a methylenedioxy group bonded to an adjacent substitution position, provided that the substituents are the same or different when there are two or more substituents; The number of G is 1, 2, 3 or 4; R is a C ₃ -C ₆ cycloalkyl group which may be substituted by a halogen atom, a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₄ alkyl group substituted with a phenyl group, a C ₁ -C ₆ haloalkyl group, or a C ₁ -C ₃ alkyl group , A C ₁ -C ₆ alkoxy group, NO ₂ , CN, -NU ¹ U ² , a naphthyl group, a C ₂ -C ₇ alkoxycarbonyl group, a substituent selected from phenyl, pyridyl and thienyl groups which may be substituted by X Wherein the substituents are the same or different when there are two or more substituents, the number of substituents R being 1, 2, 3 or 4; Y is a halogen atom, C ₁ -C ₁₀ alkyl group, C ₁ -C ₆ haloalkyl group, C ₁ -C ₆ alkoxy group, C ₁ -C ₄ alkylsulphenyl group, NO ₂ , C ₂ -C ₇ alkoxycarbonyl group and phenyl group A substituent selected, provided that when the two or more substituents are the same or different, the number of substituents Y is 1, 2, 3 or 4; W is a halogen atom, C ₁ -C ₆ alkyl group, C ₁ -C ₄ haloalkyl group, C ₁ -C ₄ alkoxy group, C ₁ -C ₄ haloalkoxy group, C ₁ -C ₄ alkylsulphenyl group, NO ₂ , C A substituent selected from a ₂ -C ₆ alkoxycarbonyl group and a C ₂ -C ₆ alkylcarbonyloxy group, provided that the substituents are the same or different when there are two or more substituents, and the number of substituents W is 1, 2, 3 , 4 or 5; T ¹ is substituted with a C ₁ -C ₂₀ alkyl group, a C ₂ -C ₆ alkenyl group, a C ₁ -C ₆ haloalkyl group, a C ₁ -C ₄ alkoxy-C ₁ -C ₄ alkyl group, or a phenyl group which may be substituted by halogen A C ₁ -C ₄ alkyl group, a C ₃ -C ₆ cycloalkyl group which may be substituted by a C ₁ -C ₃ alkyl group, a cycloalkyl group substituted by a phenyl group, a C ₂ -C ₄ alkenyl group substituted by a phenyl group, C _1- A phenyl group which may be substituted by a C ₁₂ alkoxy group, a C ₁ -C ₄ haloalkoxy group, a C ₂ -C ₅ alkenyloxy group, a benzyloxy group, a C ₂ -C ₅ alkoxycarbonyl group, -NU ¹ U ² , Z, A phenoxy group which may be substituted by Z, a phenylthio group or a 5- or 6-membered heterocyclic group which may be substituted by Z (these heterocyclic groups are selected from pyrazolyl and pyridyl); T ² and T ³ each independently represent a C ₁ -C ₆ alkoxy group; T ⁴ , T ⁵ and T ⁶ each independently represent an H or C ₁ -C ₆ alkyl group, or two of T ⁴ , T ⁵ and T ⁶ may contain an oxygen atom together with the nitrogen atom to which they are attached To form a good six-membered ring; X is a substituent selected from a halogen atom, a C ₁ -C ₄ alkyl group, a C ₁ -C ₄ alkoxy group, NO ₂ and CN, provided that the substituents are the same or different when there are two or more substituents, and The number is 1, 2, 3, 4 or 5; Z is a halogen atom, C ₁ -C ₄ alkyl group, C ₁ -C ₄ haloalkyl group, C ₁ -C ₄ alkoxy group, C ₁ -C ₄ alkylsulphenyl group, C ₂ -C ₅ alkenylsulphenyl group, NO ₂ or C A substituent selected from a _2- C ₅ alkoxycarbonyl group, provided that the substituents are the same or different when there are two or more substituents, and the number of substituents Z is 1, 2, 3, 4 or 5; And U ¹ and U ² each independently represent H, a C ₁ -C ₆ alkyl group, a C ₂ -C ₅ alkylcarbonyl group or a phenyl group. 2. The heterocyclic group according to claim 1, wherein Q is a phenyl group which may be substituted by G, a naphthyl group, or a heterocyclic group which may be substituted by R. Im), A is a phenyl group which may be substituted by W, a naphthyl group, or a heterocyclic group which may be substituted by Y (However, this heterocyclic group, R ¹ is a halogen atom, C ₁ -C ₁₀ alkyl group, C ₁ -C ₆ haloalkyl group, C ₁ -C ₆ alkoxy group, NO ₂ , CN, -NU ¹ U ² , C ₂ -C ₇ alkoxycarbonyl group, X Phenyl group, pyridyl group or thienyl group which may be substituted by; Y ¹ is a halogen atom, C ₁ -C ₁₀ alkyl group, C ₁ -C ₆ haloalkyl group, C ₁ -C ₆ alkoxy group, NO ₂ , C ₂ -C ₇ alkoxycarbonyl group or phenyl group; m represents the number of substituents and is 0, 1, 2 or 3; n represents the number of substituents and is 0, 1, 2, 3 or 4; p represents the number of substituents and is 0, 1 or 2; q represents the number of substituents and is 0 or 1 (wherein each substituent may be the same or different when m, n and p are each two or more integers). The phenyl group which may be substituted by G, the oxazolyl group which may be substituted by R, the thiazolyl group which may be substituted by R, the pyrazolyl group which may be substituted by R, Ethylene derivative which is the 1,2,3-triazolyl group which may be substituted by R, the pyridyl group which may be substituted by R, or the pyrimidinyl group which may be substituted by R. The ethylene derivative according to claim 3, wherein Q is a phenyl group which may be substituted by G. The ethylene derivative according to claim 3, wherein Q is an oxazolyl group which may be substituted by R or a 1,2,3-triazolyl group which may be substituted by R. The ethylene derivative according to claim 3, wherein Q is a thiazolyl group which may be substituted with R. The ethylene derivative according to claim 3, wherein Q is a pyrazolyl group which may be substituted with R. Q is a phenyl group which may be substituted by G, or Q-9, Q-10, Q-12, Q-13, Q-14, Q-25, Q-26, Q-28 , Ethylene derivative which is Q-30, Q-46, Q-52, Q-53 or Q-55. The ethylene derivative of claim 8 wherein Q is Q-10 or Q-46. The ethylene derivative of claim 8 wherein Q is Q-12, Q-13 or Q-14. The ethylene derivative of claim 8 wherein Q is Q-25, Q-26, Q-28 or Q-30. The ethylene derivative according to claim 8, wherein Q is a phenyl group which may be substituted with G. The phenyl group which may be substituted by W, the thiazolyl group which may be substituted by Y, the pyrazolyl group which may be substituted by Y, the pyridyl group which may be substituted by Y, or Y. Ethylene derivative which is a pyrimidinyl group which may be substituted by. The Q is a phenyl group, naphthyl group, Q-31, Q-33, Q-36, Q-37, Q-46, Q-49, A is Y ¹ is a halogen atom, C ₁ -C ₄ alkyl group, C ₁ -C ₄ haloalkyl group, C ₁ -C ₄ alkoxy group, NO ₂ or C ₂ -C ₅ alkoxycarbonyl group, Ethylene derivative wherein Y ² is a halogen atom, a C ₁ -C ₄ alkyl group, a C ₁ -C ₆ haloalkyl group, or a phenyl group. The ethylene derivative of claim 1 selected from the group consisting of: A pesticide for pest control, comprising at least one ethylene derivative according to claim 1 as an active ingredient.