Ethylene derivatives and pesticides containing said derivatives

This is a cont.-in-part of international application No. PCT/JP97/01449, filed Apr. 24, 1997.

1. Field of the Art

The present invention relates to novel ethylene derivatives, and also to agricultural chemicals and agents for preventing the attachment of aquatic organisms containing said derivatives as an active ingredient. The agricultural chemicals as referred to herein include insecticides, acaricides, nematocides, herbicides and fungicides, etc., and are especially pesticides in the field of agriculture, horticulture, stock farming and sanitation. The agent for preventing the attachment of aquatic organisms are chemicals for preventing the attachment of harmful aquatic organisms such as shells and algae to fishing nets, the bottoms of ships, marine equipment such as buoys, marine constructions, circulating water systems in thermal and atomic power plants, inlet channels for heat exchanger cooling water in chemical industry, underwater constructions and reservoirs.

2. Description of the Related Art

For acrylonitrile derivatives, Japanese Patent Application Laid-Open No. Sho 53-92769 discloses the use of 2′-chloro-3-hydroxy-2-(4-phenyl-2-thiazolyl)-cinnamoyl nitrile as an insecticide; and International Patent Application Laid-Open No. WO-95/29591 discloses its use as an aquatic adhesion inhibitor. Japanese Patent Application Laid-open No. Sho 60-11452 discloses the use of 2-(4-chlorophenyl)-3-(3-pyridyl)-3-oxopropionitrile as a herbicide and Japanese Patent Application Laid-open No. Sho 60-11401 discloses its use as a fungicide.

With the long-term use of insecticides and fungicides, recently, some pests have become resistant to chemicals and are often difficult to exterminate with conventional insecticides and fungicides. In addition, some insecticides are highly toxic and are prone to remain long, without being decomposed, to destroy the ecosystem. Accordingly, it is always expected to develop novel, low-toxic and low-persistent insecticides and fungicides.

On the other hand, in order to prevent the adhesion and growth of marine and freshwater aquatics, it is used antifouling coatings comprising organic tin compounds such as bis(tributyltin) oxide or copper compounds such as copper sulfate and cuprous oxide. However, organic tin compounds are highly toxic, though being effective in preventing the adhesion of aquatics, and are especially prone to accumulate in the bodies of fishes and shellfishes. As so promoting the environmental pollution, the use of those compounds is now under legal controls. Copper compounds are widely used in antifouling coatings for inlet channels and for the bottoms of ships. However, like tin compounds, copper compounds contain a copper as a heavy metal. Therefore, the use of copper compounds will bring about the environmental pollution in future, and agents for preventing the attachment of aquatic organisms comprising such copper compounds are not preferred. Under the above-mentioned situation, it has been desired agents for preventing the attachment of aquatic organisms that have few influences on the ecosystem and bring about little secondary pollution.

In order to solve the above-mentioned problems, the present inventors have assiduously studied to develop agricultural chemicals and agents for preventing the attachment of aquatic organisms which can exhibit excellent pesticidal activities even when used in small amounts, and which have few negative influences on non-targeted organisms such as mammals, fishes and useful insects, and, as a result, have found that the compounds mentioned hereinunder are highly safe and have excellent pesticidal activities and activities for preventing the attachment of aquatic organisms. On the basis of these findings, the present inventors have completed the present invention.

Specifically, the present invention provides the following [1] to [25]

[1] Ethylene derivatives of a formula (I):

[wherein;

Q represents a phenyl group optionally substituted by G, a naphthyl group optionally substituted by G, or a heterocyclic group optionally substituted by R (said heterocyclic group being a 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, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,4,5-tetrazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, imidazolinone, imidazolidinedione, 3(2H)-pyridazinone, benzothiazolyl, benzimidazolyl, indazolyl, benzoxazolyl, quinolyl, isoquinolyl, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl group);

A represents a phenyl group optionally substituted by W, a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y (said heterocyclic group being a 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, pyridinyl, 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, 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, then A is a phenyl group optionally substituted by W, a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y (said heterocyclic group being 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, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, 3(2H)-pyridazinone, benzothiazolyl, benzimidazolyl, indazolyl, benzoxazolyl, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl group);

(b) when Q is a 2-thiazolyl group optionally substituted by R, then A is a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y (said heterocyclic group being a 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, pyridinyl, 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, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl group);

(c) when Q is a pyridyl group optionally substituted by R, then A is a heterocyclic group optionally substituted by Y (said heterocyclic group being 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, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, 3(2H)-pyridazinone, benzothiazolyl, benzimidazolyl, indazolyl, benzoxazolyl, quinoxalinyl, phthalazinyl, cinnolinyl 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 a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y (said heterocyclic group being a 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, pyridinyl, 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, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl group);

(e) when Q is a 1,2,4-triazolyl group optionally substituted by R, then A is a heterocyclic group optionally substituted by Y (said heterocyclic group being a 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, 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, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl group);

(f) when Q is a benzothiazolyl group optionally substituted by R, then A is a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y (said heterocyclic group being a 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, pyridinyl, 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, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl group);

(g) when Q is a benzimidazolyl group optionally substituted by R, then A is a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y (said heterocyclic group being 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, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, 3(2H)-pyridazinone, benzothiazolyl, benzimidazolyl, indazolyl, benzoxazolyl, quinolyl, isoquinolyl, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl group);

(h) when Q is a phenyl group optionally substituted by G, then A is a heterocyclic group optionally substituted by Y (said heterocyclic group being a pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, 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, cinnolinyl or quinazolinyl group);

(i) when Q is a naphthyl group optionally substituted by G, than A is a heterocyclic group optionally substituted by Y (said heterocyclic group being a 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, pyridinyl, 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, quinoxalinyl, phthalazinyl, cinnolinyl or quinazolinyl group);

B represents 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 C 1 -C 4 alkyl group substituted by a phenyl group optionally substituted by a halogen or a C 1 -C 4 alkyl group, a C 1 -C 4 alkyl group substituted by a benzoyl group optionally substituted by a halogen or a C 1 -C 4 alkyl group, a tetrahydropyranyl group, (CH 3 ) 3 Si, a C 1 -C 4 alkylsulfonyl group, a phenylsulfonyl group optionally substituted by a halogen or a C 1 -C 4 alkyl group, —SO 2 CF 3 , a C 1 -C 4 monoalkylaminosulfonyl group, a C 2 -C 8 dialkylaminosulfonyl group, a phenylaminosulfonyl group, a C 2 -C 5 monoalkylaminothiocarbonyl group, a C 3 -C 9 dialkylaminothiocarbonyl group, a C 2 -C 5 cyanoalkyl group, a C 3 -C 9 alkoxycarbonylalkyl group, —C(═O)T 1 , —P(═O)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 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 C 1 -C 4 alkyl group substituted by a phenyl group optionally substituted by a halogen or a C 1 -C 4 alkyl group, a C 1 -C 4 alkyl group substituted by a benzoyl group optionally substituted by a halogen or a C 1 -C 4 alkyl group, a tetrahydropyranyl group, (CH 3 ) 3 Si, a C 1 -C 4 alkylsulfonyl group, a phenylsulfonyl group optionally substituted by a halogen or a C 1 -C 4 alkyl group, —SO 2 CF 3 , a C 1 -C 4 monoalkylaminosulfonyl group, a C 2 -C 8 dialkylaminosulfonyl group, a phenylaminosulfonyl group, a C 2 -C 5 monoalkylaminothiocarbonyl group, a C 3 -C 9 dialkylaminothiocarbonyl group, a C 2 -C 5 cyanoalkyl group, a C 3 -C 9 alkoxycarbonylalkyl group, —C(═O)T 1 , —P(═O)T 2 T 3 , or —P(═S)T 2 T 3 ;

E represents a heterocyclic group optionally substituted by a C 1 -C 4 alkyl or C 1 -C 4 haloalkyl group—(said heterocyclic group being a 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 represents a halogen, a C 2 -C 4 alkynyl group, a phenylethynyl group optionally substituted by Z, a C 1 -C 4 haloalkyl group, CN, an isonitrile group, NO 2 , N 3 , CHO, a C 2 -C 5 alkylcarbonyl group, a C 2 -C 5 alkoxycarbonyl group, a C 3 -C 5 alkenyloxycarbonyl group, a C 2 -C 4 alkylaminocarbonyl group, a C 3 -C 9 dialkylaminocarbonyl group, a benzoyl group optionally substituted by Z, an aminothiocarbonyl group, a C 1 -C 4 alkylsulfenyl group, a C 1 -C 4 alkylsulfinyl group, a C 1 -C 4 alkylsulfonyl group, a phenylsulfenyl group optionally substituted by Z, a phenylsulfinyl group optionally substituted by Z, a phenylsulfonyl group optionally substituted by Z, —P(═O)T 2 T 3 , or —P(═S)T 2 T 3 .

G is a substituent freely selected from a halogen atom, a C 1 -C 10 alkyl group, a C 2 -C 4 cyanoalkyl group, a C 1 -C 4 alkyl group substituted by a phenyl group optionally substituted by a halogen or a C 1 -C 4 alkyl group, a C 2 -C 4 alkenyl group, a C 2 -C 6 alkynyl group, a C 1 -C 6 haloalkyl group, a C 2 -C 6 haloalkenyl group, a C 2 -C 6 haloalkynyl 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 C 1 -C 10 alkoxy group, a C 2 -C 6 alkenyloxy group, a C 2 -C 6 alkynyloxy group, a C 1 -C 4 haloalkoxy group, a C 2 -C 6 haloalkenyloxy group, a C 2 -C 6 haloalkynyloxy group, a C 1 -C 4 alkylsulfenyl group, a C 1 -C 4 alkylsulfinyl group, a C 1 -C 4 alkylsulfonyl group, a C 2 -C 6 alkenylsulfenyl group, a C 2 -C 6 alkenylsulfinyl group, a C 2 -C 6 alkenylsulfonyl group, a C 2 -C 6 alkynylsulfenyl group, a C 2 -C 6 alkynylsulfinyl group, a C 2 -C 6 alkynylsulfonyl group, a C 1 -C 4 haloalkylsulfenyl group, a C 1 -C 4 haloalkylsulfinyl group, a C 1 -C 4 haloalkylsulfonyl group, a C 2 -C 6 haloalkenylsulfenyl group, a C 2 -C 6 haloalkenylsulfinyl group, a C 2 -C 6 haloalkenylsulfonyl group, a C 2 -C 6 haloalkynylsulfenyl group, a C 2 -C 6 haloalkynylsulfinyl group, a C 2 -C 6 haloalkynylsulfonyl group, CHO, NO 2 , CN, —NU 1 U 2 , OH, a naphthyl group, a methoxy group substituted by a phenyl group optionally substituted by a halogen or a C 1 -C 4 alkyl group, a C 2 -C 7 alkoxycarbonyl group, a C 2 -C 4 alkoxyalkyl group, a C 2 -C 4 alkylcarbonyl group, a C 2 -C 4 haloalkylcarbonyl group, a C 2 -C 5 alkylcarbonyloxy group, a C 2 -C 5 haloalkylcarbonyloxy group, 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 as bonded at the adjacent substituting positions, a halomethylenedioxy group as bonded at the adjacent substituting positions, and —N═CT 7 T 8 (in which T 7 and T 8 each independently represent H, or a phenyl, benzyl or C 1 -C 6 alkyl group, or T 7 and T 8 , together with the carbon atom to which they are bonded, form a 5-, 6-, 7- or 8-membered ring), (provided that when the the substituent is two or more, then said substituents may be the same or different), and the number of the substituent, G, is 1, 2, 3 or 4; or G is an alkylene group as bonded to the adjacent substituting positions to form a 5-, 6-, 7- or 8-membered ring;

R is a substituent freely selected from a halogen atom, a C 1 -C 10 alkyl group, a C 1 -C 4 alkyl group substituted by a phenyl group optionally substituted by a halogen or a C 1 -C 4 alkyl group, a C 2 -C 8 alkenyl group, a C 2 -C 6 alkynyl group, a C 1 -C 6 haloalkyl group, a C 2 -C 6 haloalkenyl group, a C 2 -C 6 haloalkynyl 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 C 1 -C 6 alkoxy group, a C 2 -C 6 alkenyloxy group, a C 2 -C 6 alkynyloxy group, a C 1 -C 4 haloalkoxy group, a C 2 -C 6 haloalkenyloxy group, a C 2 -C 6 haloalkynyloxy group, a C 1 -C 4 alkylsulfenyl group, a C 1 -C 4 alkylsulfinyl group, a C 1 -C 4 alkylsulfonyl group, a C 2 -C 6 alkenylsulfenyl group, a C 2 -C 6 alkenylsulfinyl group, a C 2 -C 6 alkenylsulfonyl group, a C 2 -C 6 alkynylsulfenyl group, a C 2 -C 6 alkynylsulfinyl group, a C 2 -C 6 alkynylsulfonyl group, a C 1 -C 4 haloalkylsulfenyl group, a C 1 -C 4 haloalkylsulfinyl group, a C 1 -C 4 haloalkylsulfonyl group, a C 2 -C 6 haloalkenylsulfenyl group, a C 2 -C 6 haloalkenylsulfinyl group, a C 2 -C 6 haloalkenylsulfonyl group, a C 2 -C 6 haloalkynylsulfenyl group, a C 2 -C 6 haloalkynylsulfinyl group, a C 2 -C 6 haloalkynylsulfonyl group, NO 2 , CN, —NU 1 U 2 , a phenoxy group, OH, a naphthyl group, a C 2 -C 7 alkoxycarbonyl group, a C 2 -C 4 alkoxyalkyl group, a C 2 -C 4 alkylcarbonyl group, a C 2 -C 5 alkylcarbonyloxy group, a C 2 -C 5 haloalkylcarbonyloxy group, a benzoyl group optionally substituted by X, a phenyl group optionally substituted by X, a pyridyl group optionally substituted by X, a thienyl group optionally substituted by X, and —N═CT 7 T 8 , (provided that when the substituent is two or more, then said substituents may be the same or different), and the number of the substituents, R, is 1, 2, 3 or 4; or R is an alkylene group as bonded to the adjacent substituting positions to form a 5-, 6-, 7- or 8-membered ring;

Y is a substituent freely selected from a halogen atom, a C 1 -C 10 alkyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkoxy group, a C 2 -C 6 alkenyloxy group, a C 2 -C 6 alkynyloxy group, a C 1 -C 4 haloalkoxy group, a C 2 -C 6 haloalkenyloxy group, a C 2 -C 6 haloalkynyloxy group, a C 1 -C 4 alkylsulfenyl group, a C 1 -C 4 alkylsulfinyl group, a C 1 -C 4 alkylsulfonyl group, a C 2 -C 6 alkenylsulfenyl group, a C 2 -C 6 alkenylsulfinyl group, a C 2 -C 6 alkenylsulfonyl group, a C 2 -C 6 alkynylsulfenyl group, a C 2 -C 6 alkynylsulfinyl group, a C 2 -C 6 alkynylsulfonyl group, a C 1 -C 4 haloalkylsulfenyl group, a C 1 -C 4 haloalkylsulfinyl group, a C 1 -C 4 haloalkylsulfonyl group, a C 2 -C 6 haloalkenylsulfenyl group, a C 2 -C 6 haloalkenylsulfinyl group, a C 2 -C 6 haloalkenylsulfonyl group, a C 2 -C 6 haloalkynylsulfenyl group, a C 2 -C 6 haloalkynylsulfinyl group, a C 2 -C 6 haloalkynylsulfonyl group, NO 2 , CN, —NU 1 U 2 , OH, a C 2 -C 7 alkoxycarbonyl group, a C 2 -C 4 alkoxyalkyl group, a C 2 -C 6 alkylcarbonyloxy group, a C 2 -C 5 haloalkylcarbonyloxy group, a C 3 -C 7 dialkylaminocarbonyloxy group, a phenyl group optionally substituted by X, and —N═CT 7 T 8 (in which T 7 and T 8 each independently represent H, or a phenyl, benzyl or C 1 -C 6 alkyl group, or T 7 and T 8 may, together with the carbon atom to which they are bonded, form a 5-, 6-, 7- or 8-membered ring), (provided that when the substituent is two or more, then said substituents may be the same or different), and the number of the substituent, Y, is 1, 2, 3 or 4; or Y is an alkylene groupas bonded to the adjacent substituting positions to form a 5-, 6-, 7- or 8-membered ring;

W is a substituent freely selected from a halogen atom, a C 1 -C 6 alkyl group, a C 1 -C 4 haloalkyl group, a C 1 -C 4 alkoxy group, a C 1 -C 4 haloalkoxy group, a C 1 -C 4 alkylsulfenyl group, a C 1 -C 4 alkylsulfinyl group, a C 1 -C 4 alkylsulfonyl group, a C 1 -C 4 haloalkylsulfenyl group, a C 1 -C 4 haloalkylsulfinyl group, a C 1 -C 4 haloalkylsulfonyl group, a C 2 -C 4 alkenyl group, a C 2 -C 4 haloalkenyl group, a C 2 -C 4 alkenyloxy group, a C 2 -C 4 haloalkenyloxy group, a C 2 -C 4 alkenylsulfenyl group, a C 2 -C 4 alkenylsulfinyl group, a C 2 -C 4 alkenylsulfonyl group, a C 2 -C 4 haloalkenylsulfenyl group, a C 2 -C 4 haloalkenylsulfinyl group, a C 2 -C 4 haloalkenylsulfonyl group, a C 2 -C 4 alkynyl group, a C 2 -C 4 haloalkynyl group, a C 2 -C 4 alkynyloxy group, a C 2 -C 4 haloalkynyloxy group, a C 2 -C 4 alkynylsulfenyl group, a C 2 -C 4 alkynylsulfinyl group, a C 1 -C 4 alkynylsulfonyl group, a C 2 -C 4 haloalkynylsulfenyl group, a C 2 -C 4 haloalkynylsulfinyl group, a C 2 -C 4 haloalkynylsulfonyl group, NO 2 , CN, a formyl group, a C 2 -C 6 alkoxycarbonyl group, a C 2 -C 6 alkylcarbonyl group, a C 2 -C 6 haloalkylcarbonyl group, a C 2 -C 6 alkylcarbonyloxy group, and —NU 1 U 2 , (provided that when the substituent is two or more, then said substituents may be the same or different), and the number of the substituent, W, is 1, 2, 3 or 4;

T 1 represents 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, a C 3 -C 6 halocycloalkyl group, a C 1 -C 4 alkyl group substituted by a phenyl group optionally substituted by a halogen or 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 cycloalkyl group substituted by a phenyl group optionally substituted by a halogen or a C 1 -C 3 alkyl group, a cyclopropyl group substituted by both a phenyl group optionally substituted by a halogen or a C 1 -C 4 alkyl group and a C 1 -C 4 alkyl group, a C 3 -C 4 cycloalkyl group substituted by both a phenyl group optionally substituted by a halogen or a C 1 -C 4 alkoxy group, and a halogen, a cyclopropyl group substituted by both a C 2 -C 4 alkenyl group optionally substituted by a halogen, and a C 1 -C 4 alkyl group, a C 2 -C 4 alkenyl group substituted by a phenyl group optionally substituted by a halogen or a C 1 -C 4 alkyl group, a C 1 -C 12 alkoxy group, a C 1 -C 4 haloalkoxy group, a C 2 -C 5 alkenyloxy group, a C 3 -C 6 cycloalkoxy group optionally substituted by a C 1 -C 3 alkyl group, a benzyloxy group, a C 2 -C 6 alkoxycarbonyl group, —NU 1 U 2 , a phenylamino group, a phenyl group optionally substituted by Z, a phenoxy group optionally substituted by Z, a phenylthio group optionally substituted by Z, a naphthyl group optionally substituted by Z, or a 5-membered or 6-membered heterocyclic group optionally substituted by Z, (said heterocyclic group being selected from 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, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl and 3(2H)-pyridazinone groups);

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

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

X and Z are independently substituents as freely selected from a halogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a C 1 -C 4 alkoxy group, a C 1 -C 4 haloalkoxy group, a C 1 -C 4 alkylsulfenyl group, a C 1 -C 4 alkylsulfinyl group, a C 1 -C 4 alkylsulfonyl group, a C 2 -C 5 alkenylsulfenyl group, a C 2 -C 5 alkenylsulfinyl group, a C 2 -C 5 alkenylsulfonyl group, a C 1 -C 4 haloalkylsulfenyl group, a C 1 -C 4 haloalkylsulfinyl group, a C 1 -C 4 haloalkylsulfonyl group, NO 2 , CN, CHO, OH, —NU 1 U 2 , a phenyl group, a phenoxy group, and a C 2 -C 5 alkoxycarbonyl group, (provided that when the substituent is two or more, then said substituents may be the same or different), and the number of the substituent, X and Z, is 1, 2, 3, 4 or 5 each;

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

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

[2] Ethylene derivatives of the above-mentioned 1], in which;

Q is a phenyl group optionally substituted by G, a naphthyl group optionally substituted by G, or a heterocyclic group optionally substituted by R, (said heterocyclic group being a 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-triazolyl, 1,2,3,4-tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,4,5-tetrazinyl, pyrazolinyl, imidazolinyl, imidazolinone or imidazolidinedione 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, said heterocyclic group being a 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, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, pyrazolinyl or imidazolinyl 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 OC 2 H 4 OCH 2 , a C 1 -C 4 alkylsulfonyl group, a phenylsulfonyl group optionally substituted by a halogen or a C 1 -C 4 alkyl group, —SO 2 CF 3 , a C 1 -C 8 dialkylaminosulfonyl group, a C 2 -C 9 dialkylaminothiocarbonyl group, a C 3 -C 9 alkoxycarbonylalkyl group, —C(═O)T 1 , —P(═O)T 2 T 8 , —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 a C 1 -C 2 O 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 C 1 -C 4 alkyl group substituted by a phenyl group optionally substituted by a halogen or a C 1 -C 4 alkyl 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 cycloalkyl group substituted by a phenyl group optionally substituted by a halogen or a C 1 -C 4 alkyl group, a cyclopropyl group substituted by both a phenyl optionally substituted by a halogen or a C 1 -C 4 alkyl group, and a C 1 -C 4 alkyl group, a C 3 -C 4 cycloalkyl group substituted by both a phenyl group optionally substituted by a halogen or a C 1 -C 4 alkoxy group and a halogen, a cyclopropyl group substituted by both a C 2 -C 4 alkenyl group optionally substituted by a halogen and a C 1 -C 4 alkyl group, a C 2 -C 4 alkenyl group substituted by a phenyl group optionally substituted by a halogen or a C 1 -C 4 alkyl group, a C 1 -C 12 alkoxy group, a C 1 -C 4 haloalkoxy group, a C 2 -C 5 alkenyloxy group, a C 3 -C 6 cycloalkoxy group optionally substituted by a C 1 -C 3 alkyl group, a benzyloxy group, a C 2 -C 6 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.

[3] Ethylene derivatives of the above-mentioned [2], in which;

Q is a phenyl group optionally substituted by G, a naphthyl group optionally substituted by G, or a heterocyclic group optionally substituted by R, said heterocyclic group being

A is a phenyl group optionally substituted by W, a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y, said heterocyclic group being

provided that, when (a) Q is any of Q-1, Q-2, Q-3 or Q-4, then A is a phenyl group optionally substituted by W, a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y, (said heterocyclic group being any of 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-66, 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, then A is a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y, (said heterocyclic group being any of 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-66, 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, then A is a heterocyclic group optionally substituted by Y, (said heterocyclic group being any of 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-60, A-63, A-64, A-65, A-66, A-67, A-68, A-69, A-70, A-71, A-72, A-73, A-74 or A-75),

(d) when Q is any of Q-23, Q-24, Q-43, Q-44, Q-45, Q-46 or Q-49, then A is a naphthyl group optionally substituted by W, or a heterocyclic group optionally substituted by Y, (said heterocyclic group being any of 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-66, A-67, A-68, A-69, A-70, A-71, A-72, A-73, A-74 or A-75),

(e) when Q is any of Q-37, Q-38, Q-39, Q-40, Q-41 or Q-42, then A is a heterocyclic group optionally substituted by Y, (said heterocyclic group being any of 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-66, 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, then A is a heterocyclic group optionally substituted by Y, said heterocyclic group being any of 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-66, 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, then A is a heterocyclic group optionally substituted by Y, (said heterocyclic group being any of 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-66, A-67, A-68, A-69, A-70, A-71, A-72, A-73, A-74 or A-75,

R 1 is selected from a halogen atom, a C 1 -C 10 alkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 alkynyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkoxy group, a 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 C 2 -C 4 alkylcarbonyl group, a phenyl group optionally substituted by X, a pyridyl group optionally substituted by X, a thienyl group optionally substituted by X, and —N═CT 7 T 8 (in which T 7 and T 8 each independently represent H, a phenyl, benzyl or C,-C, alkyl group, or T 7 and T 8 may, together with the carbon atom to which they are bonded, form a 5-, 6-, 7- or 8-membered ring); or may, together with the adjacent R, form a 5-, 6-, 7- or 8-membered ring as an alkylene group

Y 1 is selected from a halogen atom, a C 1 -C 10 alkyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkoxy group, a 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 (in which T 7 and T 8 each independently represent H, or a phenyl, benzyl or C 1 -C 6 alkyl group, or T 7 and T 8 may, together with the carbon atom to which they are bonded), form a 5-, 6-, 7- or 8-membered ring); or may, togeher with the adjacent Y 1 , form a 5-, 6- 7- or 8-membered ring an alkylene group;

X is a substituent of which the number is from 1 to 4 and which is freely selected from a halogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a C 1 -C 4 alkoxy group, a C 1 -C 4 haloalkoxy group, a C 1 -C 4 alkylsulfenyl group, a C 1 -C 4 alkylsulfinyl group, a C 1 -C 4 alkylsulfonyl group, a C 2 -C 5 alkenylsulfenyl group, a C 2 -C 5 alkenylsulfinyl group, a C 2 -C 5 alkenylsulfonyl group, a C 1 -C 4 haloalkylsulfenyl group, a C 1 -C 4 haloalkylsulfinyl group, a C 1 -C 4 haloalkylsulfonyl group, NO 2 , CN, CHO, OH, —NU 1 U 2 , a phenyl group, a phenoxy group, and a C 2 -C 5 alkoxycarbonyl group, (provided that when the number of the substituent, X, is two or more then said substituents may be the same or different);

Z is a substituent of which the number is from 1 to 4 and which is freely selected from a halogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 haloalkyl group, a C 1 -C 4 alkoxy group, a C 1 -C 4 haloalkoxy group, a C 1 -C 4 alkylsulfenyl group, a C 1 -C 4 alkylsulfinyl group, a C 1 -C 4 alkylsulfonyl group, a C 1 -C 4 alkenylsulfenyl group, a C 1 -C 4 alkenylsulfinyl group, a C 1 -C 4 alkenylsulfonyl group, NO 2 , CN, —NU 1 U 2 , a phenyl group, a phenoxy group, and a C 2 -C 5 alkoxycarbonyl group, (provided when the number of the substituent, Z, is two or more, said substituents may be the same or different);

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

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

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

q indicates the number of the substituents, and is 0 or 1;

(provided that when m, n and p each are an integer of 2 or more, the substituents may be the same or different).

[4] Ethylene derivatives of the above-mentioned [2], in which E is CN.

[5] Ethylene derivatives of the above-mentioned [5], in which E is CN.

[6] Ethylene derivatives of the above-mentioned [2], in which E is a heterocyclic group optionally substituted by a C 1 -C 4 alkyl or C 1 -C 4 haloalkyl group—(said heterocyclic group being a 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 is 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, a C 2 -C 5 alkylcarbonyl group, a C 2 -C 5 alkoxycarbonyl group, a C 2 -C 4 alkylaminocarbonyl group, a C 3 -C 9 dialkylaminocarbonyl group, a benzoyl group optionally substituted by Z, an aminothiocarbonyl group, a C 1 -C 4 alkylsulfenyl group, a C 1 -C 4 alkylsulfinyl group, a C 1 -C 4 alkylsulfonyl group, a phenylsulfenyl group optionally substituted by Z a phenylsulfinyl group optionally substituted by Z, a phenylsulfonyl group optionally substituted by Z, —P(═O)T 2 T 3 , or —P(═S)T 2 T 3 .

[7] Ethylene derivatives of the above-mentioned [3], in which E is a heterocyclic group optionally substituted by a C 1 -C 4 alkyl or C 1 -C 4 haloalkyl group—(said heterocyclic group being a 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 is a halogen atom, a C 2 -C 4 alkynyl group, a phenylethynyl group optionally substituted by a Z, a C 1 -C 4 haloalkyl group, CN, NO 2 , N 3 , CHO, a C 2 -C 5 alkylcarbonyl group, a C 2 -C 5 alkoxycarbonyl group, a C 2 -C 4 alkylaminocarbonyl group, a C 3 -C 9 dialkylaminocarbonyl group, a benzoyl group optionally substituted by Z, an aminothiocarbonyl group, a C 1 -C 4 alkylsulfenyl group, a C 1 -C 4 alkylsulfinyl group, a C 1 -C 4 alkylsulfonyl group, a phenylsulfenyl group optionally substituted by Z, a phenylsulfinyl group optionally substituted by Z, a phenylsulfonyl group optionally substituted by Z, —P(═O)T 2 T 3 , or —P(═S)T 2 T 3 .

(8] Ethylene derivatives of the above-mentioned [4], in which 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, 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] Ethylene derviatives of the above-mentioned [8], in which Q is a phenyl group optionally substituted by G.

[10] Ethylene derivatives of the above-mentioned [8], in which Q is an oxazolyl group optionally subsituted by R or a 1,2,3-triazolyl group optionally substituted by R.

[11] Ethylene derivatives of the above-mentioned [8], in which Q is a thiazolyl group optionally substituted by R.

[12] Ethylene derivatives of the above-mentioned (8], in which Q is a pyrazolyl group optionally substituted by R.

[13] Ethylene derivatives of the above-mentioned 5], in which Q is a phenyl group optionally substituted by G, or is 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-55, Q-56, or Q-57.

[14] Ethylene derivatives of the above-mentioned [7], in which Q is a phenyl group optionally subsituted by G, or is 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-55, Q-56, or Q-57.

[15] Ethylene derivatives of the above-mentioned [13), in which Q-10, Q-44, Q-45, Q-46 or Q-47.

[16] Ethylene derivatives of the above-mentioned [13], in which Q is Q-12, Q-13 or Q-14.

[17 ] Ethylene derivatives of the above-mentioned [13], in which 0 is Q-25, Q-26, Q-27, Q-28, Q-29 or Q-30.

[18 ] Ethylene derivatives of the above-mentioned [13], in which Q is a phenyl group optionally substituted by G.

[19] Ethylene derivaties of the above-mentioned 2], in which A is a phenyl group optionally substituted by W, a thiazolyl group optionally substituted by Y, a pyrazolyl group optionally substituted by Y, a pyridinyl group optionally subsituted by Y, or a pyrimidinyl group optionally substituted by Y.

[20] Ethylene derivatives of the above-mentioned [3], in which;

Q is a phenyl group optionally subsitited 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,

A is

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

Y 3 is 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] Ethylene derivatives of the above-mentioned [20], in which E is CN.

[22] Ethylene derivatives of the above-mentioned [20], in which E is a heterocyclic group optionally substituted by a C 1 -C 4 alkyl or C 1 -C 4 haloalkyl group—(said heterocyclic group being a 2-oxazolyl, 2-thiazolyl, 2-imidazolyl, 1,2,4-triazol-3-yl, 1,2,4-oxadialol-3-yl, 1,2,4-thiadiazol-3-yl or 1,3,4-oxadiazol-2-yl group)—or is 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, a C 2 -C 5 alkylcarbonyl group, a C 2 -C 5 alkoxycarbonyl group, a C 2 -C 4 alkylaminocarbonyl group, a C 3 -C 9 dialkylaminocarbonyl group, a benzoyl group optionally substituted by Z, an aminothiocarbonyl group, a C 1 -C 4 alkylsulfenyl group, a C 1 -C 4 alkylsufinyl group, a C 1 -C 4 alkylsulfonyl group, a phenylsulfenyl group optionally substituted by Z, a phenylsulfinyl group optionally substituded by Z, a phenylsulfonyl group optionally substituted by Z, —P(═O)T 2 T 3 , or —P(═S)T 2 T 3 .

[23] Ethylene derivatives of the above-mentioned [1], which are selected from the following:

[24] An agricultural chemical comprising, as the active ingredient, one or more ethylene derivatives of the above-mentioned [1] to [23].

[25] An agent for preventing the attachment of aquatic organisms containing, as an active ingredient, one or more ethylene derivatives of the above-mentioned [1] to [23].

The moiety —C(E)═C(OB)— of the compounds (I) of the present invention includes two isomers of E-form and Z-form, both of which are within the scope of the invention.

It will be understood that the compounds (I) of the present invention where the substituent B is a hydrogen atom exist as tautomers to be represented by the following:

Although the compounds (I) will exist essentially as the enol-form (1′), they could be as the tautomer form (2) under some conditions. It should be understood that the present invention includes all these three tautomers and their mixtures.

Now, preferred embodiments of 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 7 , T 8 , U 1 , U 2 , m, n, p and q are referred to hereinunder.

The heterocyclic group for Q, A and B indicates the following meanings.

Specifically, thienyl is thiophen-2-yl or thiophen-3-yl; furyl is furan-2-yl or furan-3-yl; pyrrolyl is pyrrol-1-yl, pyrrrol-2-yl or pyrrol-3-yl; oxazolyl is oxazol-2-yl, oxazol-3-yl, oxazol-4-yl or oxazol-5-yl; thiazolyl is thiazol-2-yl, thiazol-4-yl or thiazol-5-yl; imidazolyl is imidazol-1-yl, imidazol-2-yl or imidazol-4-yl; isoxazolyl is isoxazol-3-yl, isoxazol-4-yl or isoxazol-5-yl; isothiazolyl is 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; 1,3,4-oxadiazolyl is 1,3,4-oxadiazol-2-yl; 1,3,4-thiadiazolyl is 1, 4-thiadiazol-2-yl; 1,2,4-oxadiazolyl is 1,2,4-oxadiazol-3-yl or 1,2,4-oxadiazol-5-yl; 1,2,4-thiadizolyl is 1,2,4-thiadiazol-3-yl or 1,2,4-thiadiazol-5-yl; 1,2,4-traizolyl is 1,2,4-triazol-1-yl, 1,2,4-triazol-3-yl or 1,2,4-triazol-4-yl; 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-2yl or 1,2,3,4-tetrazol-5-yl; pyridinyl is pyridin-2yl, pyridin-3-yl or pyridin-4-yl; pyrimidinyl is pyrimidin-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-triazin5-yl or 1,2,4-triazin-6-yl; 1,2,4,5-tetrazinyl is 1,2,4,5-tetrazin-3-yl; 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-2yl, 1-imidazolin-4-yl or 4-imidazolin-2-yl; oxazolinyl is 2-oxazolin-2-yl, 2-oxazolin-4-yl or 2-oxazolin-5-yl; isoxazolinyl is 2-isoxazolin-3-yl, 2-isoxazolin-4-yl or 2-isoxazolin-5-yl; thiazolinyl is 2-thiazolin-2-yl, 2-thiazolin-4-yl or 3-thiazolin-2-yl; imidazolidinon-yl is imidazolidin-2-on-1-yl; imidazolinon-yl is 2-imidazolinon-1-yl; and 3(2H)-pyridazinon-yl is 3(2H)-pyridazinon-2-yl, 3(2H)-pyridazinon-4-yl, 3(2H)-pyridazinon-5-yl or 3(2H)-pyridazinon-6-yl.

Preferred scope of Q is the following groups.

QI: phenyl, 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, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-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, pyridinyl, pyrimidinyl.

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

QIV: phenyl.

QV: oxazoly.

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-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, pyridinyl, 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, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl.

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

AIV: thiazolyl, pyrazolyl, pyridinyl.

AV: thiazolyl.

AVI: pyrazolyl.

AVII: pyridinyl.

Preferred scope of B is the following groups.

BI: H, C 2 -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, phenylsulfonyl optionally substituted by halogen or C 1 -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, 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 grouips.

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 alkylsulfenyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, phenylsulfenyl 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 alkylaminocarbonyl, C 3 -C 9 dialkylaminocarbonyl, benzoyl optionally substituted by Z, aminothiocarbonyl, C 1 -C 4 alkylsulfenyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, phenylsulfenyl optionally substituted by Z, phenylsulfinyl optionally substituted by Z, phenylsulfonyl optionally substituted by Z or —P(═O)T 2 T 3 .

EIII: CN.

Preferred scope of G is the following groups.

GI: substituents freely selected from 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 haloalkynyl, 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 3 -C 4 haloalkynyloxy, C 1 -C 4 alkylsulfenyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 2 -C 4 alkenylsulfenyl, C 2 -C 4 alkenylsulfinyl, C 2 -C 4 alkenylsulfonyl, C 2 -C 4 alkylnylsulfenyl, C 2 -C 4 alkynylsulfinyl, C 2 -C 4 alkynylsulfonyl, C 1 -C 4 haloalkylsulfenyl, C 2 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 2 -C 4 haloalkenylsulfenyl, C 2 -C 4 haloalkenylsulfinyl, C 2 -C 4 haloalkenylsulfonyl, C 2 -C 4 haloalkynylsulfenyl, C 2 -C 4 haloalkynylsulfinyl, C 2 -C 4 haloalkynylsulfonyl, NO 2 , CN, —NU 1 U 2 , methoxy substituted by phenyl optionally substituted by halogen, or C 1 -C 4 alkyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 4 alkoxyalkyl, C 2 -C 4 alkylcarbonyl, C 2 -C 4 haloalkylcarbonyl, C 2 -C 4 alkylcarbonyloxy, C 2 -C 6 haloalkylcarbonyloxy, C 3 -C 7 dialkylaminocarbonyloxy, phenyl optionally substituted by Z, phenoxy optionally substituted by Z, benzoyl optionally substituted by Z, pyridyl optionally substituted by Z, and pyridyloxy optionally substituted by Z (provided that when the substituent is two or more, said substituents may be the same or different) and the number of the substituent G, is 1, 2, 3 or 4, or G is an alkylene group as bonded to the adjacent substituting positions to form a 5-, 6-, 7- or 8-membered ring

GII: substituents freely selected from halogen, C 1 -C 6 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 haloalkyl, C 1 -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 1 -C 4 alkylsulfenyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 2 -C 4 alkenylsulfenyl, C 2 -C 4 alkenylsulfinyl, C 2 -C 4 alkenylsulfonyl, C 2 -C 4 alkynylsulfenyl, C 2 -C 4 alkynylsulfinyl, C 2 -C 4 alkynylsulfonyl, C 1 -C 4 haloalkylsulfenyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 2 -C 4 haloalkenylsulfenyl, C 2 -C 4 haloalkenylsulfinyl, C 2 -C 4 haloalkenylsulfonyl, methoxy substituted by phenyl optionally substituted by halogen or C 1 -C 4 alkyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 5 alkylcarbonyloxy, C 2 -C 5 haloalkylcarbonyloxy, phenoxy optionally substituted by Z, and pyridyloxy optionally substituted by Z (provided that the number of the substituent is two or more, said substituebts may be the same or different), and the number of the substituent, G, is 1, 2 or 3.

GIII: substituents freely selected from halogen C 1 -C 6 alkyl, C 1 -C 4 haloalkyl, 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 1 -C 4 alkylsulfenyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 2 -C 4 alkenylsulfenyl, C 2 -C 4 alkenylsulfinyl, C 2 -C 4 alkenylsufonyl, C 2 -C 4 alkynylsulfenyl, C 2 -C 4 alkynylsulfinyl, C 2 -C 4 alkynylsulfonyl, C 1 -C 4 haloalkylsulfenyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 2 -C 4 haloalkenylsulfenyl, C 2 -C 4 haloalkenylsulfinyl, C 2 -C 4 haloalkenylsulfonyl, methoxy substituted by phenyl optionally 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 (provided that when the substituent is two or more, said substituents may be the same or different), and the number of the substituent, G is 1 or 2.

Preferred scope of R is the following group.

RI: substituents freely selected from halogen, C 1 -C 6 alkyl, C 1 -C 3 alkyl substituted by phenyl optionally substituted by halogen or C 1 -C 4 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl optionally substituted by C 1 -C 3 alkyl, C 1 -C 4 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 alkylsulfenyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 2 -C 4 alkenylsulfenyl, C 2 -C 4 alkenylsulfinyl, C 2 -C 4 alkenylsulfonyl, C 2 -C 4 alkynylsulfenyl, C 2 -C 4 alkynylsulfinyl, C 2 -C 4 alkynylsulfonyl, C 1 -C 4 haloalkylsulfenyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 2 -C 4 haloalkenylsulfenyl, C 2 -C 4 haloalkenylsulfinyl, C 2 -C 4 haloalkenylsulfonyl, NO 2 , CN, —NU 1 U 2 , naphthyl, C 2 -C 4 alkoxycarbonyl, C 2 -C 4 alkoxyalkyl, phenyl optionally substituted by X, pyridyl optionally substituted by X, and thienyl optionally substituted by X (provided that when the substituent is two or more, said substituents may be the same or different), and the number of the substituent, R, is 1, 2 or 3, or R is an alkylene group as bonded to the adjacent substituting positions to form a 5-, 6-, 7- or 8-membered ring.

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

RIII: substituents freely selected from halogen, C 1 -C 6 alkyl, C 1 -C 3 alkyl substituted by phenyl optionally substituted by halogen or C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl optionally substituted by C 1 -C 3 alkyl, NO 2 , CN, —NU 1 U 2 , naphthyl, C 2 -C 4 alkoxycarbonyl, phenyl optionally substituted by X, and pyridyl optionally substituted by X (provided that when the substituent is two or more, said substituents may be the same or different), and the number of the substituent R, is 1 or 2.

Depending on the type of the heterocyclic group to be substituted by R, the number of R differs. For the group of 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,3-oxadiazolyl, 1,2,3-thiadiazolyl or 1,2,3,4-tetrazolyl, the number of R is 0 or 1, preferably 1. For the group of thiazolyl, oxazolyl, isoxazolyl, isothiazolyl, 1,3,4-triazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl or 1,2,4-triazinyl, the number of R is an integer of from 0 to 2, preferably 1 or 2. For the group of thienyl, furyl, pyrazolyl, imidazolyl, pyrimidinyl, pyrazinyl or pyridazinyl, the number of R is an integer of from 0 to 3, preferably an integer of from 0 to 2, member preferably 1 or 2. For the group of pyrrolyl, pyridinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl or thiazolinyl, the number of R is an integer of from 0 to 4, preferably an integer of from 0 to 3, more preferably 1 or 2.

Preferred scope of Y is the following groups.

YI: substituents freely selected from 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 haloalkoxy, C 2 -C 4 haloalkenyloxy, C 2 -C 4 haloalkynyloxy, C 1 -C 4 alkylsulfenyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 2 -C 4 alkenylsulfenyl, C 2 -C 4 alkenylsulfinyl, C 2 -C 4 alkenylsulfonyl, C 2 -C 4 alkynylsulfenyl, C 2 -C 4 alkynylsulfinyl, C 2 -C 4 alkynylsulfonyl, C 1 -C 4 haloalkylsulfenyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 2 -C 4 haloalkenylsulfenyl, C 2 -C 4 haloalkenylsulfinyl, C 2 -C 4 haloalkenylsulfonyl, C 2 -C 4 haloalkynylsulfenyl, 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 (provided that the substituent is two or more, said substituents may be the same or different) and the number of the substituent, Y, is 1, 2 or 3.

YII: substituents freely selected from halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylsulfenyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfenyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, NO 2 ,CN, C 2 -C 4 alkoxycarbonyl, and phenyl optionally substituted by X (provided that when the substituent is two or more, said substituents may be the same or different) and the number of the substituent, Y, is 1, 2 or 3.

Depending on the type of the heterocyclic group to be substituted by Y, the number of Y differs. For the group of 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,3-thiadiazolyl or 1,2,3,4-tetrazolyl, the number of Y is 0 or 1, preferably 1. For the group of thiazolyl, oxazolyl, isoxazolyl, isothiazolyl, 1,3,4-triazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl or 1,2,4-triazinyl, the number of Y is an integer of from 0 to 2, preferably 1 or 2. For the group of thienyl, furyl, pyrazolyl, imidazolyl, pyrimidinyl, pyrazinyl or pyridazinyl, the number of Y is an integer of from 0 to 3, preferably an integer of from 0 to 2, more preferably 1 or 2. For the group of pyrrolyl, pyridinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl or thiazolinyl, the number of Y is an integer of from 0 to 4, preferably an integer of from 0 to 3, more preferably 1 or 2.

Preferred scope of W is the following group.

WI: substituents freely selected from 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 alkylsulfenyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfenyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 2 -C 4 alkenyloxy, C 2 -C 4 haloalkenyloxy, C 2 -C 4 alkenylsulfenyl, C 2 -C 4 alkenylsulfinyl, C 2 -C 4 alkenylsulfonyl, C 2 -C 4 haloalkenylsulfenyl, C 2 -C 4 haloalkenylsulfinyl, c 2 -C 4 haloalkenylsufonyl, C 2 -C 4 alkynyloxy, C 2 -C 4 alkynylsulfenyl, C 2 -C 4 alkynylsulfinyl, C 2 -C 4 alkynylsulfonyl, 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 2 (provided that when the substituent is two or more, said substituents are the same or different) and the number of the substituent, W is 1, 2, 3 or 4.

WII: substituents freely selected from 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 alkylsulfenyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfenyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 2 -C 4 alkenyloxy, C 2 -C 4 haloalkenyloxy, C 2 -C 4 alkenylsulfenyl, C 2 -C 4 alkenylsulfinyl, C 1 -C 4 alkenylsulfony, C 2 -C 4 alkynyloxy, C 2 -C 4 alkynylsulfenyl, C 2 -C 4 alkynylsulfinyl, C 2 -C 4 alkynylsulfonyl, NO 2 , and CN (provided that the substituent is two or more, said substituents may be the same or different) and the number of the substituent, W, is 1, 2 or 3.

WIII: substituents freely selected from 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 alkylsulfenyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfenyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, NO 2 , and CN (provided that when the substituent is two or more, the substituents may be the same or different) and the number of the substituent, W, is 1 or 2.

Preferred scope of T 1 is 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, C 1 -C 4 alkyl substituted by phenyl optionally substituted by halogen or C 1 -C 4 alkyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 cycloalkyl optionally substituted by C 1 -C 3 alkyl, cycloalkyl substituted by phenyl optionally substituted by halogen or C 1 -C 4 alkyl, C 2 -C 4 alkenyl substituted by phenyl optionally substituted by halogen or C 1 -C 4 alkyl, C 1 -C 10 alkoxy, C 1 -C 4 haloalkoxy, C 2 -C 6 alkenyloxy, C 3 -C 6 cycloalkoxy optionally substituted by C 1 -C 4 alkyl, benzyloxy, C 2 -C 6 alkoxycarbonyl, —NU 1 U 2 , phenyl optionally substituted by Z, phenoxy optionally substituted by Z, phenylthio optionally substituted by Z, naphthyl, and heterocyclic group optionally substituted by Z. (said heterocyclic group being selected from 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, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, and 1,2,4-triazinyl groups).

T 1 II: C 1 -C 1 alkyl, C 2 -C 6 alkenyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkoxyalkyl, C 1 -C 4 alkyl substituted by phenyl optionally substituted by halogen or C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl optionally substituted by C 1 -C 3 alkyl, cycloalkyl substituted by phenyl optionally substituted by halogen or C 1 -C 4 alkyl, C 2 -C 4 alkenyl substituted by phenyl optionally substituted by halogen or C 1 -C 4 alkyl, C 1 -C 10 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, and heterocyclic group optionally substituted by Z (said heterocyclic group selected from thienyl, furyl, 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 1 -C 4 alkoxyalkyl, C 1 -C 4 alkyl substituted by phenyl, C 3 -C 6 cycloalkyl optionally substituted C 1 -C 3 alkyl, 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 1 -C 5 alkoxycarbonyl, phenyl optionally substituted by Z, phenoxy optionally substituted by Z, phenylthio, naphthyl, pyrazolyl optionally substituted by Z or pyridinyl optionally substituted by Z.

Preferred scope of T 2 is the following groups.

T 2 I: phenyl, C 1 -C 4 alkyl, C 1 -C 4 alkoxy of C 1 -C 4 alkylsulfenyl.

Preferred scope of T 4 is the following groups.

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

Preferred scope of T 4 is the following groups.

T 4 I: H, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl or benzyl. Also preferred is such that any two of T 4 , T 5 and T 6 , together with the nitrogen atom to which they are bonded, forms a 5-, 6- or 7-membered ring optionally having oxygen, nitrogen and/or sulfur atoms.

Preferred scope of T 5 is the following groups.

T 5 I: H, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl or benzyl. Also, preferred is such that any two of T 4 , T 5 and T 6 , together with the nitrogen atom to which they are bonded, forms a 5-, 6- or 7-membered ring optionally having oxygen, nitrogen and/or sulfur atoms.

Preferred scope of TO is the following groups.

T 6 I: H, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl or benzyl. Also, preferred is such that any two of T 4 , T 5 and T 6 , together with the nitrogen atom to which they are bonded, forms a 5-, 6- or 7-membered ring optionally having oxygen, nitrogen and/or sulfur atoms.

Preferred scope of X is the following groups.

XI: substituents freely selected from 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 alkylsulfenyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 2 -C 5 alkenylsulfenyl, C 2 -C 5 alkenylsulfinyl, C 2 -C 5 alkenylsulfonyl, C 1 -C 4 haloalkylsulfenyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, NO 2 , CN, —NU 1 U 2 and C 2 -C 5 alkoxycarbonyl (provided that the substituent is two or more, said substituents may be the same or different) and the substituent X is 1,2 or 3.

XII: substituents freely selected from 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 alkylsulenyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 2 -C 5 alkenylsulfenyl, C 1 -C 4 haloalkylsulfenyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, and NO 2 (provided that when the substituent is two or more, said substituents may be the same or (different) and the number of the substituent X, is 1, 2 or 3.

XIII: substituents freely selected from halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, and C 1 -C 4 alkoxy (provided that when the substituent is two is more, said substituents may be the same or different) and the number of the substituent, X, is 1 or 2.

Depending on the type of the ring to be substituted by X, the number of X differs. For phenyl, the number of X is an integer of from 0 to 5, preferably an integer of from 0 to 3, more preferably an integer of from 0 to 2. For pyridyl, the number of X is an integer of from 0 to 4, preferably 0, 1 or 2, more preferably 0 or 1. For thienyl, the number of X is an integer of from 0 to 3, preferably 0 or 1.

Preferred scope of Z is the following groups.

ZI: substituents freely selected from 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 alkylsulfenyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 2 -C 5 alkenylsulfenyl, C 2 -C 6 alkenylsulfinyl, C 2 -C, alkenylsulfonyl, C 1 -C 4 haloalkylsulfenyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, NO 2 , CN, —NU 1 U 2 and C 2 -C 5 alkoxycarbonyl (provided that when the substituent is two or more, said substituents may be the same or different) and the number of the substituent, Z, is 1, 2, 3, or 4.

ZII: substituents freely selected from 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 alkylsulfenyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 2 -C 5 alkenylsulfenyl, C 2 -C 5 alkenylsulfinyl, C 2 -C 5 alkenylsulfonyl, C 1 -C 4 haloalkylsulfenyl, C 1 -C 4 haloalkylsulfinyl and C 1 -C 4 haloalkylsulfonyl (provided that when the substitutent is two or more, said substituents may be the same or different) and the substituent Z, is 1, 2, 3, or 4.

Depending on the type of the ring to be substituted by Z, the number of Z differs. For phenyl, the number of Z is an integer of from 0 to 5, preferably an integer of from 0 to 4, more preferably 0, 1, 2 or 3, even more preferably 0, 1 or 2. For naphthyl, the number of Z is an integer of from 0 to 7, preferably 0. Where the ring to be substituted by Z is a heterocyclic group, the number of the substituents of Z also differs depending on the type of the heterocyclic group. For the group of 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,3-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,3,4-tetrazolyl or 1,2,3,5-tetrazolyl, the number of Z is 0 or 1. For the group of thiazolyl, oxazolyl, isoxazolyl, isothiazolyl, 1,3,4-triazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl or 1,2,4-triazinyl, the number of Z is an integer of from 0 to 2, preferably 1 or 2. For the group of thienyl, furyl, pyrazolyl, imidazolyl, pyrimidinyl, pyrazinyl or pyridazinyl, the number of Z is an integer of from 0 to 3, preferably an integer of from 0 to 2, more preferably 1 or 2. For the group of pyrrolyl, pyridinyl, pyrazolinyl, imidazolinyl, oxazolinyl, isoxazolinyl or thiazolinyl, the number of Z is an integer of from 0 to 4, preferably an integer of from 0 to 2, more preferably 1 or 2.

Preferred scope of T 7 is the following groups.

T 7 I: H, phenyl, benyzl or C 1 -C 4 alkyl. Also preferred is such that T 7 and T 8 , together with the carbon atom to which they are bonded, form a 5-membered or 6-membered ring.

Preferred scope of T 8 is the following groups.

T 8 I: phenyl, benzyl or C 1 -C 4 alkyl. Also preferred is such that T 7 and T 8 , together with the carbon atom to which they are bonded, form a 5-membered or 6 -membered ring.

Preferred scope of U 1 is the following groups.

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

Preferred scope of U 2 is the following groups.

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

Preferably, m is 1, 2, or 3, more preferably 1 or 2.

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

Preferably, p is 1 or 2.

The above-mentioned preferred groups in the scopes of the preferred substituents can be optionally combined and show the scopes of the preferred compounds of the present invention. Hereinunder mentioned are especially preferred scopes.

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

Compounds of the invention comprising preferred substituents of 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, T 8 I, U 1 I and U 2 I.

Compounds of the invention comprising preferred substituents of 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, T 8 I, U 1 I and U 2 I.

Compounds of the invention comprising preferred substituents of 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, T 8 I, U 1 I and U 2 I.

Compounds of the invention comprising preferred substituents of 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 , XI, ZI, T 7 I, T 8 , U 1 I and U 2 I.

Compounds of the invention comprising preferred substituents of 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, T 8 I, U 1 I and U 2 I.

Compounds of the invention comprising preferred substituents of 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, T 8 I, U 1 I and U 1 I.

Compounds of the invention comprising preferred substituents of 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, T 8 I, U 1 I and U 2 I.

Compounds of the invention comprising preferred substituents of 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, T 8 I, U 1 I and U 2 I.

Compounds of the invention comprising preferred substituents of 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, T 8 I, U 1 I and U 2 I.

Compounds of the invention comprising preferred substituents of 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, T 8 I, U 1 I and U 2 I.

Compounds of the invention comprising preferred substituents of 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, T 8 I, U 1 I and U 2 I.

Compounds of the invention comprising preferred substituents of 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, T 8 I, U 1 I and U 2 I.

Compounds of the invention comprising preferred substituents of QVIII, AIII, Bill, 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, T 8 I, U 1 I U 2 .

Compounds of the invention comprising preferred substituents of QIX, AIII, Bill, 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, T 8 I, U 1 I and U 2 I.

Compounds of the invention comprising preferred substituents of 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, T 8 I, U 1 I and U 2 I.

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

Compounds of the invention comprising preferred substituents of 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, T 8 I, U 1 I and U 2 I.

Now specific examples of 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 7 , T 8 , U 1 and U 2 are mentioned below.

The halogen atom for E, G, R, R 1 , W, X, Y, Y 1 , Y 2 , Y 3 and Z includes a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Preferred are a fluorine atom, a chlorine atom and a bromine atom.

The alkyl group for 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 , Y 3 and Z may be a straight chain or branched alkyl group having indicated carbon atoms, which includes, 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 groups.

The alkenyl group for G, R, R 1 , T 1 , T 4 , T 5 , T 6 , Y 1 and W may be a straight chain or branched alkenyl group having indicated carbon atoms, which includes, 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-2-propenyl and 1-ethyl-1-methyl-2-propenyl groups.

The alkynyl group for E, G, R, R 1 , Y 1 and W may be a straight chain or branched alkynyl group having indicated carbon atoms, which includes, for example, 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 ,1a-dimethyl-2-butynyl, 1 1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl and 2-ethyl-3-butynyl groups.

The haloalkyl group for B, E, G, R, R 1 , T 1 , W, X, Y, Y 1 , Y 2 , Y 3 and Z may be a straight chain or branched haloalkyl group having indicated carbon atoms, which includes, for example, fluoromethyl, chloromethyl, bromomethyl, fluoroethyl, chloroethyl, bromoethyl, fluoro-n-propyl, chloro-n-propyl, difluoromethyl, chlorodifluoromethyl, trifluoromethyl, dichloromethyl, trichloromethl, difluoroethyl, trifluoroethyl, trichloroethyl, chlorodifluoromethyl, bromodifluoromethyl, trifluoroethyl, hexafluoro-n-propyl, chlorobutyl, fluorobutyl, chloro-n-pentyl, fluoro-n-pentyl, chloro-n-hexyl and fluoro-n-hexyl groups.

The C 3 -C 6 cycloalkyl group optionally substituted by a C 1 -C 3 alkyl group for G, R, T 1 , T 4 , T 5 and T 6 includes, for example, cyclopropyl, 1-methylcyclopropyl, 2,2,3,3-tetramethylcyclopropyl, cyclobutyl, 1-ethylcyclobutyl, 1-n-butylcyclobutyl, cyclopentyl, 1-methylcyclopentyl, cyclohexyl, 1-methylcyclohexyl and 4-methylcyclohexyl groups.

The C 1 -C 4 alkyl group substituted by a phenyl group optionally substituted by a halogen atom or a C 1 -C 4 alkyl group for B, G, R and T 1 includes, for example, benzyl, 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-chlorophenyl)-2-methylpropyl and 2-methyl-2-(3-methylphenyl)propyl groups.

For T 1 , the C 3 -C 6 cycloalkyl group substituted by a phenyl group optionally substituted by a halogen atom or a C 1 -C 4 alkyl group includes, for example, 1-phenylcyclopropyl, 1-(3-chlorophenyl)cyclopropyl, 1-(4-chlorophenyl)cyclopropyl, 1-(4-bromophenyl)cyclopropyl, 1-(4-fluorophenyl)cyclopropyl, 1-(4-ethylphenyl) cyclopropyl, 1-(4-propylphenyl)cyclopropyl, 2-phenylcyclopropyl, 1-phenylcyclobutyl, 2-phenylcyclobutyl, 1-phenylcyclopentyl, 1-(4-chlorophenyl)cycloptentyl, 2-phenylcyclopentyl, 3-phenylcyclopentyl, 1-phenylcyclohexyl, 1-(3-fluorophenyl)cyclohexyl, 1-(4-chlorophenyl)cyclohexyl, 1-(4-tert-butylphenl)cyclohexyl, 2-phenylcyclohexyl, 3-phenylcyclohexyl and 4-phenylcyclohexyl groups.

For T 1 , the cyclopropyl group substituted by both a phenyl group optionally substituted by a halogen atom or a C 1 -C 4 alkyl group and a C 1 -C 4 alkyl group includes, for example, 2,2-dimethyl-1-phenylcyclopropyl, 1-(4-chlorophenyl)-2,2-dimethylcyclopropyl, 2,2-dimethyl-3-phenylcyclopropyl, 3-(3-chrlorophenyl)-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 (4-tert-butylphenyl)-2,2-dimethyl-3-phenylcyclopropyl groups.

For T 1 , the C 3 -C 4 cycloalkyl group substituted by both a phenyl group optionally substituted by a halogen atom or a C 1 -C 4 alkoxy group and a halogen atom includes, for example, 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)cyclopropyl, 2,2-dichloro-(4-i-propyloxyphenyl)cyclopropyl, 2,2-dichloro-(4-t-butylphenyl)cyclopropyl, 2,2-dichloro-1-(4-methoxyphenyl)-3-phenylcyclopropyl and 1-(4-ethoxyphenyl)-2,2,3,3-tetrafluorobutyl groups.

For T 1 , the cyclopropyl group substituted by both a C 2 -C 4 alkenyl group optionally substituted by a halogen atom, and a C 1 -C 4 alkyl group includes, for example, 2,2-dimethyl-3-(2,2-dimethylethenyl)cyclopropyl, 3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropyl, 3-(2,2-dichloroethyenyl)-2,2-dimethylcyclopropyl and 3-(2,2-chlorotrifluoroethenyl)-2,2-dimethylcyclopropyl groups.

For T 1 , the C 3 -C 6 cycloalkoxy group optionally substituted by a C 1 -C 3 alkyl group includes, for example, cyclopropoxy, cyclobutoxy, cyclopentoxy, cyclohexyloxy and 1-methylcyclopropoxy groups.

For T 1 , the C 2 -C 4 alkenyl group substituted by a phenyl group optionally substituted by a halogen atom or a C 1 -C 4 alkyl group includes, for example, 1-phenylethenyl, 2-phenylethenyl, 2-(2-chlorophenyl)ethenyl, 2-(3-chlorophenyl)ethenyl, 2-(4-chlorophenyl)ethenyl, 2-(4-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-(2,4,6-trimethylphenyl)-1-propenyl groups.

The alkoxy group for G, R, T 1 , T 2 , T 3 , R 1 , W, X, Y, Y 1 , Y 2 and Z may be straight chain or branched alkoxy group having indicated carbon atoms, which includes, for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentyloxy, 1-methylbutyloxy, 2-methylbutyloxy, 3-methylbutyloxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropyloxy, n-hexyloxy, 1-methylpentyloxy, 2-methylpentyloxy, 3-methylpentyloxy, 4-methylpentyloxy, 1,1-dimethylbutyloxy, 1,2-dimethylbutyloxy, 1,3-dimethylbutyloxy, 2,2-dimethylbutyloxy, 2,3-dimethylbutyloxy, 3,3-dimethylbutyloxy, 1-ethylbutyloxy, 2-ethylbutyloxy, 1,1,2-trimethylpropyloxy, 1,2,2-trimethylpropyloxy, 1-ethyl-1-methylpropyloxy, 1-ethyl-2-methylpropyloxy, n-heptyloxy, n-octyloxy, n-nonyloxy and n-decyloxy groups.

The C 3 -C 6 halocycloalkyl group for G, R and T 1 includes, for example, fluorocyclopropyl, difluorocyclopropyl, chlorocyclopropyl, dichlorocyclopropyl, 1-methyl-2,2-dichlorocyclopropyl, chlorocyclobutyl, dichlorocyclobutyl, chlorocyclopentyl, dichlorocyclopentyl, chlorocyclohexyl, dichlorocyclohexyl and tetrafluorocyclobutyl groups.

The group —NU 1 U 2 for G, R, R 1 , T 1 , W, X, Y, Y 1 and Z includes, for example, 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, diethylamino, di-n-propylamino, diisopropylamino, di-n-butylamino, di-sec-butylamino, diisobutylamino, di-n-pentylamino, di-n-hexylamino, methylethylamino, methylpropylamino, methylisopropylamino, methylbutylamino, methyl-sec-butylamino, methylisobutylamino, methyl-tert-butylamino, methylpentylamino, methylhexylamino, ethylpropylamino, ethylisopropylamino, ethylbutylamino, ethyl-sec-butylamino, ethyl-isobutylamino, ethylpentylamino, ethylhexylamino, phenylamino, benzylamino, N-merthylacetamido, N-ethylacetamido, N-phenylacetamido and N-acerylacetamido groups, to which is applied the indicated scope of the carbon atoms constituting it.

The C 2 -C 5 alkoxycarbonyl group for E, G, R, R 1 T 1 , W, X, Y, Y 1 , Y 2 and Z includes, for example, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, iso-propoxycarbonyl, n-butoxycarbonyl, sec-butoxycarbonyl, iso-butoxycarbonyl and tart-butoxycarbonyl groups.

The C 1 -C 4 haloalkoxy group for G, R, T 1 , W, X, Y and Z may be a straight chain or branched C 1 -C 4 haloalkoxy group, including, for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, dichlorofluoromethoxy, chloromethoxy, dichloromethoxy, trichloromethoxy, bromomethoxy, fluorcethoxy, chlorcethoxy, bromcethoxy, difluoroethozy, trifluoroethoxy, tetrafluoroethoxy, pentafluorcethoxy, trichloroethoxy, trifluorochlorethoxy, fluoropropoxy, chloropropoxy, bromopropoxy, fluorobutoxy, chlorobutoxy, fluoro-iso-propoxy and chloro-iso-propoxy groups.

The C 1 -C 4 alkylsulfenyl group for E, G, R, T 2 , T 3 , W, X, Y and Z includes, for example, methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, iso-butylthio, sec-butylthio and tert-butylthio groups.

The C 1 -C 4 alkylsulfinyl group for E, G, R, X, W, Y and Z includes, for example, methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, iso-propylsulfinyl, n-butylsulfinyl, iso-butylsulfinyl, sec-butylsulfinyl and tart-butylsulfinyl groups.

The C 1 -C 4 alkylsulfonyl group for B, E, G, R, W, X, Y and Z includes, for example, methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, iso-propylsulfonyl, n-butylsulfonyl, iso-butylsulfonyl, sec-butylsulfonyl and tart-butylsulfonyl groups.

The C 2 -C 4 alkoxyalkyl group for B, G, R, R 1 , T 1 , Y, Y 1 and Y 2 includes, for example, C 1 -C 3 alkoxy-methyl, C 1 -C 2 alkoxy-ethyl, methoxyethoxymethyl and methoxypropyl groups.

The C 2 -C 4 alkylcarbonyl group for E, G, R, R 1 , U 1 , U 2 , Y 1 , Y 2 and W includes, for example, acetyl, propionyl, butanoyl and iso-butanoyl groups.

The C 2 -C 6 haloalkylcarbonyl group for G and W includes, for example, chloroacetyl, trifluoroacetyl, 3,3,3-trifluoropropionyl and pentafluoropropionyl groups.

The C 2 -C 5 haloalkylcarbonyloxy group for G, R and Y includes, for example, chloroacetyloxy, trifluoroacetyloxy, 3,3,3-trifluoropropionyloxy and pentafluoropropionyloxy groups.

The C 3 -C 7 dialkylaminocarbonyloxy group for G and Y includes, for example, dimethylaminocarbonyloxy, diethylaminocarbonyloxy and di-i-propylaminocarbonyloxy groups.

The naphthyl group for R, Y, Z and T 1 includes, for example, 1-naphthyl and 2-naphthyl groups.

The pyridyl group optionally substituted by Z for G and T 1 includes, for example, 2-pyridyl, 3-pyridyl and 4-pyridyl groups all optionally substituted by Z. Preferred are 2-pyridyl and 3-pyridyl groups both optionally substituted by Z; and more preferred is a 2-pyridyl group optionally substituted by Z.

The pyridyloxy group optionally substituted by Z for G and T 1 includes, for example, 2-pyridyloxy, 3-pyridyloxy and 4-pyridyloxy groups all optionally substituted by Z.

The pyridyl group optionally substituted by X for R and R 1 includes, for example, 2-pyridyl, 3-pyridyl and 4-pyridyl groups all optionally substituted by X. Preferred are 2-pyridyl and 3-pyridyl groups both optionally substituted by X; and more preferred is a 2-pyridyl group optionally substituted by X.

The pyridyloxy group optionally substituted by X for N and R 1 includes, for example, 2-pyridyloxy, 3-pyridyloxy and 4-pyridyloxy groups all optionally substituted by X.

The thienyl group-optionally substituted by X for R and R 1 includes, for example, 2-thienyl and 3-thienyl groups both optionally substituted by X.

The thienyl group optionally substituted by Z for G and Y 1 includes, for example, 2-thienyl and 3-thienyl groups both optionally substituted by Z.

The group —N═CT 7 T 8 for G, R, R 1 , Y and Y 1 indicates an alkylidenamino group, a benzylidenamino group, an arylidenamino group or a cycloalkylidenamino group, including, for example, methylidenamino, ethylidenamino, propylidenamino, isopropylidenamino, 4-methyl-2-pentylidenamino, cyclopentylidenamino and cyclohexylidenamino groups.

The C 2 -C 4 alkylaminocarbonyl group for E includes, for example, methylaminocarbonyl, ethylaminocarbonyl and n-propylaminocarbonyl groups.

The C 3 -C 9 dialkylaminocarbonyl group for E includes, for example, dimethylaminocarbonyl, diethylaminocarbonyl, di-n-propylaminocarbonyl, di-isopropylaminocarbonyl and di-n-butylaminocarbonyl groups.

The C 1 -C 4 alkylaminosulfonyl group for B includes, for example, methylaminosulfonyl, ethylaminosulfonyl, n-propylaminosulfonyl, isopropylaminosulfonyl and n-butylaminosulfonyl groups.

The C 2 -C 8 dialkylaminosulfonyl group for B includes, for example, dimethylaminosulfonyl, diethylaminosulfonyl, di-n-propylaminosulfonyl, di-isopropylaminosulfonyl and di-n-butylaminosulfonyl groups.

The C 2 -C 5 alkylaminothiocarbonyl group for B includes, for example, methylaminothiocarbonyl, ethylaminothiocarbonyl, n-propylaminothiocarbonyl, isopropylaminothiocarbonyl and n-butylaminothiocarbonyl groups.

The C 3 -C 9 dialkylaminothiocarbonyl group for B includes, for example, dimethylaminothiocarbonyl, diethylaminothiocarbonyl, di-n-propylaminothiocarbonyl, di-isopropylaminothiocarbonyl and di-n-butylaminothiocarbonyl groups.

The C 1 -C 4 alkyl group substituted by a benzoyl group optionally substituted by a halogen atom or a C 1 -C 4 alkyl group for B includes, for example, phenacyl, 2-fluorophenacyl, 3-chlorophenacyl, 4-bromophenacyl, 2-methylphenacyl,3-ethylphenacyl,4-i-propylphenacyl and 4-t-butylphenacyl groups.

The phenylsulfonyl group optionally substituted by a halogen atom or a C 1 -C 4 alkyl group for B includes, for example, 2-fluorophenylsulfonyl, 4-fluorophenylsulfonyl, 2-chlorophenylsulfonyl, 4-chlorophenylsulfonyl, 4-bromophenylsulfonyl, 2,5-dichlorophenylsulfonyl, pentafluorophenylsulfonyl, 4-methylphenylsulfonyl, 2-methylphenylsulfonyl, 4-t-butylphenylsulfonyl, 2,5-dimethylphcnylsulfonyl, 2,4-dimethylphenylsulfonyl, 2,4,6-trimethylphenylsulfonyl and 2,4,6-tri-i-propylphenylsulfonyl groups.

The C 2 -C 5 cyanoalkyl group for G and B includes, for example, cyanomethyl, 2-cyanoethyl, 3-cyanopropyl and 1-cyano-1-methylethyl groups.

The C 3 -C 9 alkoxycarbonylalkyl group for B may be a straight chain or branched one, including, for example, methoxycarbonylmethyl, ethoxycarbonylmethyl, n-propoxycerbonylmethyl, 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-methylpropyl groups.

The alkali metal for B includes, for example, lithium sodium and potassium.

The alkaline earth metal for H includes, for example, magnesium, calcium, strontium and barium. Preferred are magnesium, calcium and barium.

The ammonium group of NHT 4 T 5 T 6 for B includes, for example, ammonium, monomethylammonium, dimethylammonium, trimethylammonium, diethylammonium, triethylammonium, di-isopropylammonium, di-isopropylethylammonium, hexylmethylammonium, cyclopropylmethylammonium, cyclohexylmethylammonium, allylmethylammonium, benzylmethylammonium and 4-methylcyclohexylethylammonium groups. Any two of T 4 , T 5 and T 6 may form, along with the nitrogen atom to which they are bonded, a heterocyclic, 5-, 6-, 7- or 8-membered ammonium group optionally having oxygen, nitrogen and/or sulfur atoms.

The methoxy group substituted by a phenyl group optionally substituted by a halogen atom or a C 1 -C 4 alkyl group for G includes, for example, benzyloxy, 2-chlorobenzyloxy, 3-chlorobenzyloxy, 4-chlorobenzyloxy, 3-methylbenzyloxy, 4-t-butylbenzyloxy, 2,6-difluorobenzyloxy and 2-fluoro-4-chlorobenzyloxy groups.

The heterocyclic, 5-, 6-, 7- or 8-membered ammonium group optionally having oxygen, nitrogen and/or sulfur atoms, which is formed by two of T 4 , T 5 and T 6 along with the nitrogen atom to which they are bonded, includes, for example, pyrrolidine, pyrazolidine, imidazolidine, oxazolidine, isoxazolidine, thiazolidine, piperazine, piperazine, morpholine, thiamorpholine, hexamethylenimine and heptamethylenimine groups. The haloalkylsulfenyl group for G, R, W, X, Y and Z may be a straight chain or branched C 1 -C 4 haloalkylthio group, including, for example, fluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio, trifluoromethylthio, trichloromethylthio, 2,2,2-trifluoroethylthio, 1,1,2,2-tetrafluoroethylthio, fluoroethylthio, pentafluoroethylthio and fluoro-iso-propylthio groups.

The haloalkylsulfinyl group for G, R, W, X, Y and Z may be a straight chain or branched, C 1 -C 4 haloalkylsulfinyl group, including, for example, fluoromethylsulfinyl, chlorodifluoromethylsulfinyl, bromodifluoromethylsulfinyl, trifluoromethylsulfinyl, trichloromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 1,1,2,2-tetrafluoroethylsulfinyl, fluorcethylsulfinyl, pentafluoroethylsulfinyl and fluoro-iso-propylsulfinyl groups.

The haloalkylsulfonyl group for G, R, W, X, Y and Z may be a straight chain or branched, C 2 -C 4 haloalkylsulfonyl group, including, for example, fluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, trifluoromethylsulfonyl, trichloromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 1,1,2,2-tetrafluoroethylsulfonyl, ftuoroethylsulfonyl, pentafluoroethylsulfonyl and fluoro-isopropylsulfonyl groups.

The heloalkenyl group for G, R, T 1 and W may be a straight chain or branched C2-C 4 haloalkenyl group, including, for example, 2-chloroethenyl, 2-bromoethenyl-and 2,2-dichloroethenyl groups.

The alkenyloxy group for G, R, R 1 , T 1 , W, Y and Y 1 may be a straight chain or branched C 2 -C 4 alkenyloxy group, including, for example, allyloxy, 2-propenyloxy, 2-butenyloxy and 2-methyl-2-propenyloxy groups.

The haloalkenyloxy group for G, R, W and Y may be a straight chain or branched C 2 -C 5 haloalkenyloxy group, including, for example, 3-chloro-2-propenyloxy, 3,3-dichloro-2-propenyloxy, 4-chloro-2-butenyloxy, 4,4-dichloro-3-butenyloxy and 4,4-difluoro-3-butenyloxy groups.

The alkenylsulfenyl group for G, R, W, X, Y and Z may be a straight chain or branched C 2 -C 4 alkenylsulfenyl group, including, for example, allylsulfenyl, 2-propenylsulfenyl, 2-butenylsulfenyl and 2-methyl-2-propenylsulfenyl groups.

The alkenylsulfinyl group for G, R, W, X, Y and Z may be a straight chain or branched C 2 -C 5 alkenylsulfinyl group, including, for example, allylsulfinyl, 2-propenylsulfinyl, 2-butenylsulfinyl and 2-methyl-2-propenylsulfinyl groups.

The alkenylsulfonyl group for G, R, W, X, Y and Z may be a straight chain or branched C 2 -C 4 alkenylsulfonyl group, including, for example, allylsulfonyl, 2-propenylsulfonyl, 2-butenylsulfonyl and 2-methyl-2-propenylsulfonyl groups.

The haloalkenylsulfenyl group for G, R, W and Y may be a straight chain or branched C, C, haloalkenylsulfenyl group, including, for example, 3-chloro-2-propenylsulfenyl, 4-chloro-2-butenylsulfenyl, 3,3-dichloro-2-propenylsulfenyl, 4,4-dichloro-3-butenylsulfenyl and 4,4-difluoro-3-butenylsulfenyl groups.

The haloalkenylsulfinyl group for G, R, W and Y may be a straight chain or branched C 2 -C 4 haloalkenylsulfinyl group, including, for example, 3-chloro-2-propenylsulfinyl, 3,3-dichloro-2-propenylsulfinyl, 4-chloro-2-butenylsulfinyl, 4,4-dichloro-3-butenylsulfinyl and 4,4-difluoro-3-butenylsulfinyl groups.

The haloalkenylsulfonyl group for G, R, W and Y may be a straight chain or branched C 2 -C 4 haloalkenylsulfonyl group, including, for example, 3-chloro-2-propenylsulfonyl, 3,3-dichloro-2-propenylsulfonyl, 4-chloro-2-butenylsulfonyl, 4,4-dichloro-3-butenylsulfonyl and 4,4-difluoro-3-butenylsulfonyl groups.

The C 2 -C 4 haloalkynyl group for G, R and W includes, for example, chloroethynyl, bromoethynyl, iodoethynyl, 3-chloro-1-propynyl and 3-bromo-1-butynyl groups.

The C 2 -C 4 alkenyloxy group for G, R, W and Y includes, for example, 2-propynyloxy, 2-butenyloxy and 1-methyl-2-propynyloxy groups.

The C 2 -C 4 haloalkenyloxy group for G, R, W and Y includes, for example, 3-chloro-2-propynyloxy, 3-bromo-2-propynyloxy and 3-iodo-2-propynyloxy groups.

The C 2 -C 6 alkenylsulfenyl group for G, R, W and Y includes, for example, 2-propynylsulfenyl, 2-butynylsulfenyl and 1-methyl-2-propynylsulfenyl groups.

The C 2 -C 6 alkenylsulfinyl group for G, R, W and Y includes, for example, 2-propynylsulfinyl, 2-butenylsulfinyl and 1-methyl-2-propynylsulfinyl groups.

The C 2 -C 6 alkenylsulfonyl group for G, R, W and Y includes, for example, 2-propynylsulfonyl, 2-butynylsulfonyl and 1-methyl-2-propynylsulfonyl groups.

The C 2 -C 6 haloalkenylsulfenyl group for G, R, W and Y includes, for example, 3-chloro-2-propynylsulfenyl, 3-bromo-2-propynylsulfenyl and 3-iodo-2-propynylsulfenyl groups.

The C 2 -C 6 haloalkenylsulfinyl group for G, R, W and Y includes, for example, 3-chloro-2-propynylsulfinyl, 3-bromo-2-propynylsulfinyl and 3-iodo-2-propynylsulfinyl groups.

The C 2 -C 6 haloalkynylsulfonyl group for G, R, W and Y includes, for example, 3-chloro-2-propynylsulfonyl, 3-bromo-2-propynylsulfonyl and 3-iodo-2-propynylsulfonyl groups.

The C 2 -C 4 alkylcarbonyloxy group for G, R, W and Y includes, for example, acetoxy, propanoyloxy, butanoyloxy and isopropylcarbonyloxy groups.

The benzoyl group optionally substituted by X for E and G includes, for example, benzoyl, 2-chlorobenzoyl, 3-chlorobenzoyl, 4-chlorobenzoyl, 4-bromobenzoyl, 4-fluorobenzoyl, 3-methylbenzoyl, 4-methylbenzoyl, 4-tert-butylbenzoyl and 3,4-dichlorobenzoyl groups.

Even at low concentration, the compounds of the present invention effectively prevent various pests, which include, for example, so-called agricultural insect pests that injure agricultural and horticultural crops and trees, so-called live-stock insect pests that live on livestock and poultry, so-called sanitary insect pests that have various negative influences on the human living environment including houses, so-called stored products insect pests that injure grains stored in storehouses, and also acarids, nematodes, molluscs and crustaceans that live in the same sites as above and injure those mentioned above.

Examples of insect pests, stands, nematodes, molluscs and crustaceans capable of being exterminated by the compounds of the present invention are mentioned below, which, however, are not limitative.

Insect pests of Lepidoptera, such as rice stem borer ( Chilo suppressalis Walker), rice leafroller ( Cnaphalocrocis medinalis Guenée), green rice caterpillar ( Naranga aenescens Moore), rice skipper ( Parnara guttata Bremer et Gvey), diamond back moths ( Plutella xylostella Linneé), cabbage armyworms ( Mamestra brassicae Linneé), common white ( Pieris rapae crucivora Boisduval), turnip moth ( Agrotis segetum Denis et Schiffermüller), common cutworn ( Spodptera litura Fabricius), beet armyworm ( Spodoptera exigua Hübner), smaller tea tortrix (Adoxophyes sp.), oriental tea tortrix ( Homona magnanima Diakonoff), peach fruit moth ( Carposina niponensis Walsingham), oriental fruit moth ( Grapholita molests Busck), summer fruit tortrix ( Adoxophyes orana fascists Walsingham), apple leafminers ( Phyllonorycter ringoniella Matsumura), corn earworm ( Helicoverpo zea Boddie), tobacco bad worms ( Heliothis virescens Fabricius), European corn borer ( Ostrinia nubilalis Hübner), fall armyworm ( Spodoptera frugiperda J. E. Smith), Codling moth moth ( Cydia pomonella Linneé), fall webworms ( Hyphantria cunea Drury), etc.;

Insect pests of Hemiptera, such as green rice leafhopper ( Nephotettix cincticeps Uhler), brown rice planthoppers ( Nilaparvata lugens Stal), green peach aphid ( Myzus persicae Sulzer), cotton aphid ( Aphis gossypii Glover), green-house whitefly ( Trialeurodes vaporariorum Westwood), sweetpotato white fly ( Bemisia tabaci Gennadius), pear psylla ( Psylla pyricola Forster), azalea lace bug ( Stephanitis pyrioides Scott), arrowhead scale ( Unaspis yanonensis Kuwana), comstock mealybug ( Pseudococcus comrtocki Kuwana), red wax scale ( Ceroplastes rubens Maskell), brown-mamrorated stinkbug (Halyomorpha mists Uhler), cabbage bug ( Eurydema rugosam Motschulsky), bed bug ( Cimex lectularius Linneé), etc.;

Insect pests of Coleoptera, such as twenty-eight-spotted ladybird ( Henosepilachna vigintioctopunctata Fabricius), cupreous chafers ( Anomala cuprea Hope), ricewater weevil ( Lissorhoptrus oryzophilus Kuschel), sweetpotato weevil ( Cylas formicarius Fabricius), cucurbit leaf beetle ( Aulacophora femoralis Motschulsky), striped flea beetle (Phyllotreta striolata Fablicius), white-spotted longicom beetle ( Anoplophora malasiaca Thomson), pine sawyers ( Monochamus alternatus Hope), corn rootworms (Diabrotica spp.), rice weevil ( Sitophilus zeamais Motschulsky), lesser rice weevil ( Sitophilus oryzae Linneé), granary weevils ( Sitophilus granarius Linneé), red four beetle ( Tribolium casianeum Herbst), etc.;

Insect pests of Diptera, such as legume leafminer ( Liriomyza trifolii Burgess), seedcorn maggot ( Delis platura Meigen), Hessia fly ( Mayetiola destructor Say), melon fly (Dacus (Zengodacus) cucurbitae Coquillett), Mediterranear fruit fly ( Ceratitis capitata Wiedemann), house flies ( Musca domestics Linneé), stable fly ( Stomoxys calcitrans Linneé), Sheep ked ( Melophagus orinus ), common cattle grub ( Hypoderm lineatum devillers), nothern cattle grub ( Hypoderma baris Linneé), sheep botfly ( Oestrus ovis Linneé), tsetse fly ( Golossina palpalis Robineau-Desvoidy), common gnat ( Culex pipiens pollens Coquillett), yellow-fever mosquitoes ( Aedes aegypti Linneé), Anopheles culicifacies ), etc.

Insect pests of Hymenoptera, such as cabbage sawfly ( Athalis rosae ruficornis Jakovlev), pine sawfly ( Neodiprion sertifer Geoffroy), chestnut sawfly ( Apethymus kuri Takeuchi), etc.;

Insect pests of Thysanoptera, such as melon thrips ( Thrips palmi Karny), onion thrips ( Thrips tabaci Lindeman), western flower thrips ( Frankliniella occidentalis Pergande), flower thrip ( Frankliniella intonsa Trybom), yellow tea thrip ( Scirtothrips dorsalis Hood), etc.;

Insect pests of Dictyoptera, such as smokybrown cockroache ( Periplaneta fuliginosa Serville), Japanese cockroach ( Periplaneta japonica Kamy), German cockroaches ( Blattella germanica Linneé), etc.;

Insect pests of Orthoptera, such as oriental migratory locust ( Locusts migratoria Linneé), rice grasshopper ( Oxya yezoensis Shiraki), desert locust ( Schistocetca gregaria Forskal), etc.;

Insect pests of Isoptera, such as Formosan subterranean tetmit ( Coptotermes formosanus Shiraki), ( Reticulitermes Leucotermes speratus Kolbe), ( Odontotermes formosanus Shirakif), etc.;

Insect pests of Siphonaptera, such as cat fleas ( Ctenocephalides felis Bouché), human fleas ( Pulex irritans Linneé), oriental rat flea ( Xenopsylla cheopis Rothschild), etc.;

Insect pests of Mallophaga, such as Chicken bodylouse ( Menacanthus stramineus Nitsch), cattle biting louse ( Bavicola bovis Linneé), etc.;

Insect pests of Anoplura, such as short-nosed cattle louse ( Haematopinus eurysternus Nitzsh), hog louse ( Haematopinus suis Linneé), longnosed cattle louse ( Linognathus vituli Linneé), little cattle louse ( Solenopates capillatus Enderlein), etc.

Pests of TETRANYCHIDAE, such as citrus red mite ( Panonychus cirri McGregor), European red mite ( Panonychus ulmi Kock), two-spotted spider mite ( Tetranychus urticae Koch), Kanzawa spinder mite ( Tetranychus kanzawai Kishida), etc.;

Pests of ERIOPHYDAE, such as pink citrus rust mite ( Aculops pelekassi Keifor), pear rust mite ( Epitrimerus pyri Nalepa), dry bulb mite ( Aceria tulipae Keiter), pink tea mite ( Acaphylla theae watt), etc.;

Pests of TARSONEMIDAE, such as broad mites ( Polyphagotarsonemus lotus Banks), cyclamen mite, strawberry mite ( Steneotarsonemus pallidus Banks), etc.;

Pests of ACARIDAE, such as mold mite, copra mite, forage mite ( Tyrophagus putrescetiae Schrank), bulb mite ( Rhizoglyphus robini Claparede), etc.;

Pests of VARROIDAE, such as bee brood mite ( Varroa jacobsoni Oudemans), etc.;

Pests of Ixodidae, such as bull ticks ( Boophilus microplus Canestrini), ( Haemaphysalis longicornis Neumann), etc.;

Pests of Sarcoptidae, such as sarcoptes mange mite ( Sarcaptes scabiei Linneé), etc.;

Nematodes, such as southern root-knot nematode ( Meloidogyne incognito Kofoid et White), northern root-knot nematode ( Meloidogyne hapla Chitwood), Cobb root-lesion nematode ( Pratylenchus penetrous Cobb), walnut root-lesion nematode ( Pratylenchus vulnus Allen et Jensen), potato cyst nematode ( Globodera rostochiensis Wollenweber), pine wood nematode ( Bursaphelenchus xylophilus Steiner et Buhrer), etc.;

Mollusca, such as apple snail ( Pomacea canaliculata Lamarck), ( Incilaria pilineata Benson), ( Acusta despecta sieboldiana Pfeiffer), ( Euhadra peliomphala Pfeiffer), pillbug ( Armadillidium vulgare Latreille), etc.;

Crustaceans, such as pillbug ( Armadillidium vulgare Latreille), etc.

The plant diseases to be controlled by the compounds of the present invention are as follows:

Blast ( Pyricularia oryzae ), Helminthosporium leaf spot ( Cochliobalus miyabeanus ) and Sheath blight ( Rhizoctonia solani ) of rice,

Powdery mildew ( Erysiphe graminis f. sp. hordei, f. sp. tritici), Leaf stripe ( Pyrenophora graminea ), Net blotch ( Pyrenophora teres ), Fusarium blight ( Gibberella zeae ), yellow rust, black stem rust and brown rust ( Puccinia striijormis, P. graminis, P. recondita and P. hondei ), Snow blight and snow mold (Typhula sp., Micronectriella nivais ), Loose smut ( Ustilago tritici, U. nuda ), Eyespot ( Pseudocercorsporella herpotrichoides ), Scald and leaft blotch ( Rhynchosporium secalis ), Speckled blotch ( Septoria tritici ), and Glume blotch ( Leptosphaeria nodorum ) of barley and wheat,

Melanose ( Diaporthe citri ), Scab ( Elsinoe fawcetti ) and Common green mold and blue mold ( Penicillium digitatum, P. italicum ) of citrus fruit,

Blossom blight ( Sclerotinia mali ), Canker ( Valsa mali ), Powder mildew ( Podosphaera leucotricha ), Alternaria leaft spot ( Alternaria mali ) and Scab ( Yenturia inaequalis ) of apple,

Scab ( Yenturia nashicola ), Black spot (Alternaria Kikuchiana) and Rust ( Gymnosporangium haraeanum ) of pear,

Brown rot ( Sclerotinia cinerea ), Scab ( Cladosporium carpophilum ), and Phomopsis rot (Phomopsis sp.) of peach,

Downy mildew ( Plasmopara viticola ), Anthracnose ( Elsinoe ampelina ), Ripe rot ( Glomerella cingulata ), Powdery mildew ( Uncinula nacator ) and Rust ( Phakopsora Ampelopsidis ) of grape,

Anthracnose ( Gloesporium kaki ), Powdery mildew ( Phyllactinia kakicole ), Angular leaf spot ( Cercospora kaki ), and Circular leaf spot ( Mycosphaerella nawae ) of persimmon,

Downy mildew ( Pseudoperenospora cubensis ), Anthracnose ( Colletotrichum lagenarium ), Powdery mildew ( Sphaerotheca fuliginea ), and Gummy stem blight ( Mycosphaerella melonis ) of cucurbit.

Late blight ( Phytophthora injestans ), Early blight ( Alternaria solani ) and Leaf mold ( Cladosporium fulvam ) of tomato.

Brown spot ( Phomopsis vexans ) and Powdery mildew ( Erysiphe cichoracoarum ) of egg plant,

Alternaria leaft spot ( Alternaria japonica ) and white spot ( Cerocosporella brassicae ) of vegetable of the family crucifers.

Rust ( Puccinia allii ) of Welsh onion.

Purple seed stain ( Cercospora kikuchii ), Sphaceloma scab ( Elsinoe glycines ) and Pot and stem blight ( Diaporthe phaseololum ) of soybean,

Anthracnose ( Collectorichum lindemuthianum ) of kidney bean.

Leaf spot ( Mycosphaerella personatum ) and Brown leaf spot ( Cercospora arachidicola ) of peanut,

Powdery mildew ( Erysiphe pisi ) of garden pea,

Early blight ( Alternaria solani ) of potato,

Powdery mildew ( Sphaerotheca humuli ) of strawberry,

Net blister blight ( Exobasidium reticulatum ) and White scab ( Elsinoe leucospila ) of tea,

Brown spot ( Alternaria longipes ), Powdery mildew ( Erysiphe cichoracearum ) and Anthracnose ( Colletorrichum tabacum ) of tobacco,

Cercospora leaft spot ( Cercospora beticolo ) of sugar beat,

Black spot ( Diplocarpon rosae ) and Powdery mildew ( Sphaerotheca pannosa ) of rose,

Leaf spot ( Septoria chrysanthemiindici ) and Rust ( Puccinia horiana ) of chrysanthemum,

Grey mold ( Botrytis cinerea ) of various kinds of crops, and,

Sclerotinia rot ( Sclerotinia sclerotiorum ) of various kinds of crops.

In addition, the compounds of the present invention are effective in preventing the attachment of aquatic organisms, even at extremely low concentrations. Aquatic organisms to which the invention is directed are, for example, shellfishes and algae, such as mussel, barnacle, oyster, hydrozoan, hydra, Serpula, ascidian, seamoss, Bagula, mud pond snail, sea lettuce, green lever, Ectocarpus, etc.

Specifically, the compounds of the present invention can effectively eztertninete various pests and phytopathogenic microbes of, for example, Orthoptera, Hemiptera, Lepidoptera, Coleoptera, Hymenoptera, Diptera, Temitidae, and also mites and louses, even when used at low concentrations. In addition, the compounds of the invention are effective in preventing the attachment of various aquatic organisms living in sea water and fresh water to aquatic constructions, etc. On the other hand, the compounds of the present invention contains useful compounds that have few negative influences on mammals, fishes, shellfishes and useful insects.

Of the compounds of the invention, those having CN as E can be produced according to the following methods (Scheme 1).

In (Scheme 1), Q, A and B have the same meanings as defined above; L represents a suitable leaving group, such as a chlorine atom, a bromine atom, an iodine atom, an alkoxy group having from 1 to 4 carbon atoms, a phenoxy group, an alkylsulfonyloxy group having from 1 to 4 carbon atoms, a benzenesulfonyloxy group, a toluenesulfonyloxy group, a phenoxy group, a 1-pyrazolyl group or a 1-imidazolyl group; L′ represents a halogen atom; and alkyl represents an alkyl group preferably having from 1 to 4 carbon atoms. Method A in (Scheme 1) is to react 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 compounds (1′) of the present invention. The compound (1′) of the invention is optionally reacted with an alkyl halide, an alkyl sulfonate, a trimethylsilyl halide, a sulfonyl chloride, a sulfamoyl chloride, a thiocarbamoyl chloride, an acid chloride or an ester of formula (8) to be converted into compounds (1) of the invention. Depending on the type of B in the compounds (l) of the invention, the compound (1′) is reacted with a dihydropyran, an isocyanate or a thioisocyanate to give the compounds (1). In Method A, if the compound of formula (4) or (5) is used in an excessive amount, the compounds (1) can be directly obtained without isolating the compounds (1′).

Where Q is bonded to the acrylonitrile moiety via a nitrogen atom, compounds (1′) may be produced according to Method B. Method B is to react a heterocyclic compound of formula (6) with a halogenocyanoketone derivative of formula (7) to give compounds (1′) of the invention. Where A is bonded to the acrylonitrile moiety via a nitrogen atom, compounds (1′) may be produced according to Method C. Method C is to react a cyanoacetic acid derivative of formula (9) with a heterocyclic compound of formula (10) to give compounds (1′) of the invention. As the case may be, the compound of formula (9) will be prepared by reacting an acetonitrile derivative of formula (3), such as that used in Method A, with a carbonic acid ester in the presence of a base.

Of the compounds of the invention, those where E is

In (Scheme 2), Q, A, E, B, L, L′ and alkyl have the same meanings as above.

Method D in (Scheme 2) is to react a compound of formula (11) with an acid chloride, ester or amide of formula (4) or with an acid anhydride of formula (5) to give the compounds (1′) of the present invention. The compound (1′) of the invention is optionally reacted with an alkyl halide, an alkyl sulfonate, a trimethylsilyl halide, a sulfonyl chloride, a sulfamoyl chloride, a thiocarbamoyl chloride, an acid chloride or an ester of formula (8) to be converted into the compounds (1) of the invention. Depending on the type of B in the compounds (1) of the invention, the compound (1′) is reacted with a dihydropyran, an isocyanate or a thioisocyanate to give the compounds (1). In Method A, if the compound of formula (4) or (5) is used in an excessive amount, the compounds (1) can be directly obtained without isolating the compounds (1′).

Where Q is bonded to the ethylene moiety via a nitrogen atom, the compounds (1′) may be produced according to Method E. Method E is to react a heterocyclic compound of formula (6) with a compound of formula (12) in the presence of a base to give compounds (1′) of the-invention.

Where A is bonded to the ethylene moiety via a nitrogen atom, the compounds (1′) may be produced according to Method F. Method F is to react a compound of formula (13) with a heterocyclic compound of formula (10) through dealcoholation to give the compounds (1′) of the invention. As the case may be, the compound of formula (13) will he prepared by reacting a compound of formula (11), such as that used in Method D, with a carbonic acid ester in the presence of e base.

If desired, the compounds (1′) where E is an alkoxycarbonyl group may be hydrolyzed, decarbozylated and halogenated to give the compounds of the invention where E is a halogen atom. As the case may be, the compounds of the invention where E is a halogen atom may be reacted with a nucleophilic reagent corresponding to E (e.g., triester phosphites, alkyl mercaptans, thiophenols, metal acerylides, metal cyanides, metal azides, nitrites) to give different compounds of the invention. Also as the case may be, the compounds to be obtained through decarboxylation of the compounds (1′) where E is an alkoxycarbonyl group may be reacted with an electrophilic reagent under basic conditions to give the compounds of the invention.

As the case may be, the processes of (Scheme 1) and (Scheme 2) are preferably effected in the presence of a base. The base to be used includes, for example, alkali metal alkoxides such as sodium ethoxide, sodium methoxide and t-butoxy potassium; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; organic bases such as triethylamine, pyridine and DBU; organic lithium compounds such as butyl lithium; lithium amides such as lithium diisopropylamide and lithium bistrimethylsilylamide; and sodium hydride.

The reactions of (Scheme 1) and (Scheme 2) may be effected in a solvent that is inert to the reaction. The solvent includes, for example, lower alcohols such as methanol and ethanol; aromatic hydrocarbons such as benzene and toluene; etherd such as diethyl ether, tetrahydrofuran, 1,4-diozane, 1,2-dimethoxyethane and 1,2-diethoxyethane; halogenated hydrocarbons such as methylene chloride, chloroform and 1,2-dichloroethene; amides such as dimethylformamide and dimethylacetamide; acetonitrile; dimethylsulfoxide; and mixed solvents of these. As the case may be, also employable are mixed solvent comprising said solvents and water. Also as the case may be, a quaternary ammonium salt such as tetra-n-butylammonium bromide may be added to the reaction system as a catalyst to obtain good results. The reaction temperature may be freely settled within a range between −30° C. and 200° C. Preferably, the reaction temperature falls between 0° C. and 150° C., or between 0° C. and the boiling point of the solvent if used. The base may be used in an amount of from 0.05 to 10 equivalents, preferably from 0.05 to 3 equivalents, of the reaction substrate.

The compounds of the present invention may be separated from reaction mixtures according to any ordinary methods. If the purification of the compounds of the invention is needed, they can be separated and purified by any ordinary methods of, for example, recrystallization or column chromatography.

Of the compounds of the invention, those having an asymmetric carbon atom include optically-active compounds of (+) forth and (−) form.

Methods of producing the compounds (3) to be used in (Scheme 1) are referred to hereinunder. The compounds (3) can be produced according to the following (Scheme 3).

1) A benzyl halide, a benzyl alkylsulfonate, a benzyl arylsulfonate, a halomethyl-heterocyclic compound, an alkylsulfonyloxymethyl-heterocyclic compound or an arylsulfonyloxymethyl-heterocyclic compound of formula (14) is reacted with a suitable cyanating reagent to give compounds (3). Alternatively, a phenylacetic acid derivative or a heterocyclic acetic acid derivative is converted into the corresponding amide derivative, which is then dehydrated to give compounds (3).

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

3) To obtain compounds (3) where Q is bonded to the ethylene moiety via e nitrogen atom, a heterocyclic derivative (6) where the nitrogen atom of Q is unsubstituted is reacted with a haloacetonitrile derivative in the presence of a base. Alternatively, the compound (6) is reacted with a compound (18) in the presence of a base to give a compound (17), said compound (18) being obtained through halogenation of a cyanoacetate, and thereafter the compound (17) is hydrolyzed and decarbozylated to obtain the compounds (3).

The compounds (11) to be used in (Scheme 2) can be produced in the same manner as in the production of the compounds (3) mentioned above.

The compounds (7) to be used in (Scheme I) can be produced by condensing a benzoic acid halide or heterocyclic carboxylic acid halide with a cyanoacetate in the presence of a base followed by halogenating the resulting condensate.

The above-mentioned halomethyl-heterocyclic compounds, alkylsulfonyloxymethyl-heterocyclic compounds and arylsulfonyloxymethyl-heterocyclic compounds can be derived from heterocyclic methane derivatives or heterocyclic carboxylate derivatives that are produced according to ordinary methods (see Alan R. Katritzky, and Charles W. Rees; Comprehensive Heterocyclic Chemistry, Vol. 2, Vol. 3, Vol. 4, Vol. 5 or Vol. 6). To produce the compounds (14) where Q is an oxazol-4-yl or thiazol-4-yl group, a carboxylic acid amide or thioamide can be reacted with 1,3-dichloro-2-propanone.

Examples of the compounds of the present invention are shown in Table 1 to Table 14 below. The abbreviations in these Tables are for the meanings mentioned below:

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

Where the compounds of the present invention are used as pesticides, in general, they can be mixed with a suitable carrier, for example a solid carrier, such as clay, talc, bentonite, diatomaceous earth or white carbon, or a liquid carrier such as water, alcohols (e.g., isopropanol, butanol, benzyl alcohol, furfuryl alcohol), aromatic hydrocarbons (e.g., toluene, xylene), ethers (e.g., anisole), ketones (e.g., cyclohexanone, isophorone), esters (e.g., butyl acetate), acid amides (e.g., N-methylpyrrolidone) or halogenated hydrocarbons (e.g., chlorobenzene), optionally along with other additives such as surfactant, emulsifier, dispersing agent, penetrating agent, spreading agent, thickener, anti-freezing agent, anti-caking agent and stabilizer, and can be formulated into any desired forms for practical use, such as liquid preparations, emulsions, wettable powders, dry flowables, flowables, dusts and granules.

Where the compounds of the present invention are used as agricultural chemicals, they can be combined with any other herbicides, various insecticides, acaricides, nematecides, fungicides, plant growth regulators, synergists, fertilizer and soil improvers, when they are formulated into preparations for practical use or while they are actually used through spraying or the like.

In particular, the combination of the compounds of the invention and other agricultural chemicals or plant hormones will be advantageous in that the amount of the chemicals to be used can be reduced thereby resulting in the reduction of the costs for the treatment, and that the mixed chemicals exhibit synergistic effects to broaden the insecticidal spectrum while displaying higher pesticidal activities. If desired, the compounds of the invention can be combined with e plurality of known agricultural chemicals. For the agricultural chemicals capable of being combined with the compounds of the invention, for example, the compounds described in Farm Chemicals Handbook, 1994 are referred.

Their concrete general names are raised below. However, the present invention is not necessarily limited by them.

Fungicide: acibenzolar, ampropyfos, anilazine, azaconezole, azoxystrobin, benalaxyl, benodanil, benomyl, benzamecril, binapacryl, biphenyl, bitertanol, bethoxazine, Bordeaux mixture, blesticidin-S, bromoconazole, bupirimate, buthiobate, calcium polysulfide, captafol, captan, copper oxychloride, caryropamid, carbendazim, carboxin, chinomethionat, chlobrnthiazone, chlorfenazol, chloroneb, chlorothalonil, chlozolinete, cufraneb, cymoxanil, cyproconazol, cyprodinil, cyprofuram, debacarb, dichlorophen, diclobutrazol, dichlofluanid, diclomezine, dicloran, diethofencarb, diclocymet, difenoconazole, diflumetorim, dimethirimol, dimethomorph, diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dithianon, dodemorph, dodine, drazoxolon, edifenphos, epoxiconazole, etaconazole, ethirimol, etridiazole, famoxadone, fenarimol, febuconazole, fenfuram, fenpiclonil, fenpropidin, fenpropimorph, fentin, ferbam, ferimzone, fluazinam, fludioxonil, fluoroimide, fluquinconazole, flusilazole, flusulfamide, flutolanil, flutriefol, folpet, fosetyl-aluminium, fuberidazole, furalaxyl, fenamidone, fenhexamid, guazatine, hexechlorobenzene, hexaconazole, hymexazol, imazalil, imibenconazole, iminoctedine, ipconazole, iprobenfos, iprodione, isoprothiolane, iprovalicarb, kasugamycin, kresoxim-methyl, mancopper, mancozeb, maneb, mepanipyrim, mepronil, metalaxyl, metconazole, metiram, metominostrobin, myclobutenil, nabam, nickel bis (dimethyldithiocarbamate), nitrothal-isopropyl, nuarimol, octhilinone, ofurace, oxadixyl, oxycarboxin, oxpoconazole fumarate, pefuaoate, penconazole, pencycuron, phthalide, piperalin, polyoxins, probenazole, prochloraz, procymidone, propamocarb hydrochloride, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilon, quinoxyfen, quintozene, sulfur, spiroxamine, tebuconazole, tecnazene, tetreconazole, thiabendazole, thifluzamide, thiophanate-methyl, thiram, tolclofos-methyl, tolylfluanid, triadimefon, toriadimenol, triazoxide, tricyclezole, tridemorph, triflumizole, triforine, triticonazole, validamycin, vinclozolin, zineb, ziram.

Bacteriazide: streptomycin, oxyterracycline, oxolinic acid.

Nematicide: aldoxycarb, cadusafos, fosthiazate, fosthietan, oxemyl, fenamiphos.

Acaricide: acequinocyl, acrinathrin, amitraz, bifenazate, bromopropylate, chinomethionat, chlorobezilate, clofentezine, cyhexatine, dicofol, dirnochlor, etoxazole, frnazaquin, fenbutatin oxide, fenpropathrin, fenproximate, halfenprox, hexythiazox, milbemectin, phenisobromolate, polynactins, propargite, pyridaben, pyrimidifen, tebufenpyrad, tetradifon.

Insecticide: abamectin, acephate, ecetamipirid, alanycarb, azinphos-methyl, bendiocarb, benfuracarb, bensultap, bifenthrin, Batillus thuringiensis , buprofezin, butocarboxim, carberyl, carbofuran, carbosulfan, cartap, chlorfenapyr, chlorpyrifos, chlorfenvinphos, chlorfluazuron, clothianidin, chromafenozide, chlorpyrifos-methyl, cyanox, cycloprothrin, cyfluthrin, beta-cyfluthrin, cypermethrin, cyromezine, cyhalothrin, lambda-cyhalothrin, deltamethrin, diafenthiuron, diazinon, diecloden, dichlorvos, diflubenzuron, dimethylvinphos, diofenolan, disulfoton, dimethoate, emamectin-benzoate, EPN, esfenvalerate, ethiofencarb, endosulfan, ethiprole, ethylthiometone, etofenprox, etrimfos, fenitrothion, fenobucarb, fenothiocarb, fenthion, fenoxycarb, fenpropathrin, fenvalerate, fipronil, flucythrinate, flufenoxuron, flufenprox, tau-fluvalinate, fonophos, formetenate, formothion, furathiocerb, halofenozide, hexaflumuron, hydramethylnon, imidacloprid, isofenphos, indoxacarb, isoprocerb, isoxathion, lufenuron, malathion, metaldehyde, methamidophos, methidathion, methacrifos, metalcarb, methomyl, methoprene, methoxychlor, methoxyfenozide, monocrotophos, muscalure, nicotin-sulfate, nitenpyram, omethoate, oxydemeton-methyl, oxamyl, parathion, parathion-methyl, permethrin, phenthoete, phoxim, phorate, phosalone, phosmet, phosphamidon, pirimicarb, pirimiphos-methyl, profenofos, propafos, prothiofos, pymetrozine, pyraclofos, pyridafenthion, pyriproxyfen, rotenone, sulprofos, silafluofen, spinosad, sulfotep, tebfenozide, teflubenzuron, tefluthorin, terbufos, tetrachlorvinphos, thiodicarb, thiamethoxam, thiocyclam, thiofanox, thiometon, tolfenpyrad, tralomethrin, trichlorfon, triazuron, triflumuron, vamidothion.

The dose of the compounds of the present invention varies depending on an application place, an application time, an application method, cultivation crops, etc. In general, it may be between approximately 0.005 kg and 50 kg per hectare (ba) in terms of the amount of the active ingredient.

Now, formulation examples comprising the compounds of the invention are mentioned below, which, however, are not intended to restrict the scope of the invention. In the following formulation examples, “part” or “parts” are by weight.

The others include, for example, anti-caking agent, etc.

The others include, for example, anti-freezing agent, thickener, etc.

Where the compounds of the present invention are used as an agent for preventing the attachment of aquatic organisms, they may be formulated into various preparations of, for example, coating paints, solutions, emulsions, pellets or flakes to be applicable to various objects. Depending on the application place, the object and the form, the preparations can be used in any ordinary manners of, for example, coating, spraying, dipping, adding to water or installing in water. To prepare such coating paints, solutions, emulsions and others, employable are any ordinary methods. Apart from the above-mentioned preparations and modes of using the compounds of the present invention, the compounds may also be used, for example, by incorporating them into ropes or fiber materials for fishing nets in the stage of preparing the ropes or fiber materials to thereby making them have the ability to prevent the attachment of aquatic organisms thereto. The agents for preventing the attachment of aquatic organisms according to the present invention can be used either singly or as combined with any other agents for preventing the attachment of aquatic organisms.

Where the aquatic adhesion inhibitors of the invention are used in the form of antifouling coatings, for example, the compounds of the invention may be mixed with film-forming agents to prepare coatings. The film-forming agents include oil varnishes, synthetic resins, artificial rubbers, etc. If desired, solvents, pigments and others can be added to the coatings. To prepare the paints, the uppermost limit of the concentration of the compounds of the invention to be therein is not specifically limited, provided that the resulting coatings can form film, but may be from 1 to 50% by weight, preferably from 5 to 20% by weight, relative to the weight of the antifouling coatings.

Where the agents for preventing the attachment of aquatic organisms of the present invention are used in the form of solutions, for example, the compounds of the invention may be dissolved in solvents along with film-forming agents to prepare solutions. The film-forming agents include synthetic resins, artificial rubbers, natural resins, etc. The solvents include xylene, toluene, cumene, methyl ethyl ketone, methyl isobutyl ketone, acetone, etc. If desired, additives such as plasticizer may be added to the solutions. To prepare the solutions, the uppermost limit of the concentration of the compounds of the invention to be therein is not specifically limited, provided that the compounds are dissolved to give solutions, but may be from 1 to 50% by weight, preferably from 5 to 30% by weight, relative to the weight of the solutions.

Where the agents for preventing the attachment of aquatic organisms of the present invention are used in the form of emulsions, surfactants are added to the compounds of the invention to prepare the intended emulsions according to ordinary methods of preparing general emulsions. In this, the type of the surfactants to be used is not specifically limited. To prepare the emulsions, the uppermost limit of the concentration of the compounds of the invention to be therein is not specifically limited, provided that the compounds are emulsified to give emulsions, but may be from 1 to 50% by weight, preferably from 5 to 30% by weight, relative to the weight of the emulsions.

Where the agents for preventing the attachment of aquatic organisms of the present invention are used in the form of pellets or flakes, for example, the constitutive components of the compounds of the invention and optionally plasticizers, surfactants and others are added to the base of hydrophilic resins which are solid at room temperature, such as polyethylene glycol in a solid form, and the resulting mixtures are shaped into pellets or flakes through melting molding, compression molding or the like. To prepare the pellets or flakes, the uppermost limit of the concentration of the compounds to be therein is not specifically limited, provided that the compounds can be shaped into pellets or flakes, but may be from 20 to 95% by weight, preferably from 30 to 90% by weight, relative to the weight of the pellets or flakes.

The present invention is illustrated specifically by referring to the following Synthesis Examples, Formulation Examples and Test Examples, which, however, are not intended to restrict the scope of the invention.

Synthesis Example 1

Synthesis of 2-{3-(2,6-difluorophenyl)pyrazol-1-yl}-3-(1-methyl-3,5-dichloropyrazol-4-yl)-3-hydroxyacrylonitrile

(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 thereto at room temperature, and heated under reflux for 5 hours. After acetonitrile was distilled off under reduced pressure, 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 residual product was recrystallized from a mixed solvent to isopropylether 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 dissolved in 10 ml of THF was dropwise added to a suspension of 0.15 g of 55% sodium hydride in 10 ml of THF, at 50° C. After the resulting product was stirred for 30 minutes, a solution of 0.67 g of 1-(1-methyl-3,5-dichloropyrazole-4-carbonyl)pyrazole dissolved in 10 ml of THF was dropwise added thereto at 50° C. and then stirred overnight at room temperature. The reaction mixture was poured into water, then 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 residual product was recrystallized from a mixed solvent of isopropyl ether/ethyl acetate=3/1 to obtain 0.52 g of 2-{3-(2,6-diflyuorophenyl)pyrazol-1-yl}-3-(1-methyl-3,5-dichloropyrazol-4-yl)-3-hydroxyacrylonitrile.

Synthesis Example 2

Synthesis of 3-(1-methyl-3,5-dichloropyrazol-4-yl)-2-(2-phenylthiazol-4-yl)-3-hydroxyacrylonitrile

(Compound No. II-1)

1) 2.33 g of thiobenzamide was dissolved in 20 ml of dry methanol, and 2.16 g of 1,3-dichloroacetone was added thereto at room temperature and then heated under reflux for 1 hour. The solvent was distilled off under reduced pressure, and ice water was added to the remaining product, which was then neutralized with an aqueous solution of sodium hydrogen carbonate. The resulting product was extracted with ethyl acetate, washed with saturated saline, and dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residual product was purified through silica gel column chromatography to obtain 2.03 g of 4-chloromethyl-2-phenylthiazole was obtained from the fraction eluted 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, and then heated under reflux for 10 hours. After the temperature was returned to room temperature, ethyl acetate was added the resulting mixture, and the insoluble solid was removed through filtration. The resulting ethyl acetate solution was washed with saturated saline and water, and dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residual product was purified through silica gel column chromatography to obtain 0.98 g of 4-cyanomethyl-2-phenylthiazole from the fraction eluted with chloroform.

3) 0.72 g of 4-cyanomethyl-2-phenylthiazole was dissolved in 10 ml of dry THF, and 4.6 ml of n-butyl lithium (1.56 M hexane solution) was dropwise added thereto at −60° C. or lower in an argon atmosphere. After the resulting product was stirred at −60° C. or lower for 20 minutes, 0.84 g of 1-methyl-3,5-dichloropyrazole-4-carbonyl chloride as dissolved in 3 ml of dry THF was dropwise added thereto at −60° C. or lower. Then, the resulting product was gradually heated, and stirred for 4 hours at room temperature. The reaction mixture was poured into ice water, acidified with diluted hydrochloric acid, extracted with ethyl acetate, and washed with saturated saline. The resulting product was dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residual product was purified through silica gel column chromatography to obtain the intended product from the fraction eluted with chloroform. The resulting product was crystallized and washed with diethyl ether to obtain 0.86 g of 3-(1-methyl-3,5-dichloropyrazol-4-yl)-2-(2-phenylthiazol-4-yl)-3-hydroxyacrylonitrile.

Synthesis Example 3

Synthesis of 3-(1-methyl-3-trifluoromethyl-5-chloropyrazol-4-yl)-2-(4-tert-butylthiazol-2-yl)-3-pivaloyloxyacrylonitrile

(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 and stirred to give a uniform solution. 0.16 g of pivaloyl chloride was dropwise added to the solution with cooling with ice, then gradually heated, and stirred at room temperature for 8 hours. The reaction mixture was poured into ice water, extracted with ethyl acetate, and washed thrice with saturated saline. After having been dried over sodium sulfate, the resulting product was passed through a short column filled with silica gel. The solvent was distilled off under reduced pressure, and the residual product was applied to silica gel thin-layer chromatography (developer solvent: chloroform) to obtain 0.16 g of 3-(1-methyl-3-trifluoromethyl-5-chloropyrazol-4-yl)-2-(4-tert-butylthiazol-2-yl)-3-pivaloyloxyacrylonitrile (III-6) and 0.35 g of its geometric isomer (III-15).

Compound No. III-6

1 H-NMR (CDCl 3 , δ ppm); 1.18 (9H, s), 1.32 (9H, s), 3.85 (3H, s), 6.88 (1H, s)

Compound No. III-15

1 H-NMR (CDCl 3 , δ ppm); 1.33 (9H, s), 1.39 (9H, s), 3.94 (3H, s), 7.03 (1H, s)

Reference Example

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

1) 21.35 g of phosphorus oxychloride was dropwise added to 4.72 g of DMF at 10° C. or lower. After the temperature of the reaction solution was returned to room temperature, the reaction mixture was stirred for 1 hour, and 10.71 g of 1-methyl-3-trifluoromethyl-5-pyrazolone was added thereto. The resulting mixture was heated up to 110° C., and stirred for 7 hours. After having been left to be at 70° C. the reaction mixture was poured into ice water. After pH of the mixture was made to be about 4 with an aqueous solution of sodium hydroxide added thereto, and precipitated crystals were taken out through filtration and dried to obtain 10.55 g of 1-methyl-3-trifluoromethyl-5-chloropyrazole-4-carbaldehyde.

2) 8.88 g of 1-methyl-3-2-(tert-trifluoromethyl-5-chloropyrazole-4-carbaldehyde 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. After having been heated up to 60° C., the resulting mixture was stirred for 2 hours. Next, the temperature of the mixture was return to room temperature, and the solid was removed through filtration. The resulting filtrate was acidified with an aqueous solution of hydrochloric acid, and precipitated crystals were taken out through filtration, washed with water, and dried. The thus-obtained crystals were added to 150 ml of chloroform, and heated under reflux, and the insoluble solid was removed through filtration at a heating time. Chloroform was distilled off under reduced pressure, and 6.24 g of 1-methyl-3-trifluoromethyl-5-chloropyrazole-4-carboxylic acid was obtained.

Synthesis Example 4

Synthesis of 2-(2-tert-butylthiazol-4-yl)-3-(2-methyl-4-trifluoromethylthiazol-5-yl)-3-benzoyloxyacrylonitrile

(Compound No. II-75)

In the same manner as above, the above-mentioned compound was synthesized (viscous liquid, E-Z mixture).

1 H-NMR (CDCl 3 , δ ppm); 1.09 (9H, s), 2.75 (3H, s), 7.3-7.6 (4H, m), 8.05-8.25 (2H, m): major 1.19 (9H, s), 2.70 (3H, s), 7.3-7.6 (4H, m), 8.05-8.25 (2H, m): minor

Synthesis Example 5

Synthesis of 2-(4-trifluoromethylphenyl)-3-(1-methyl-3,5-dichloropyrazol-4-yl)-3-(1-methyl-3,5-dichloropyrazole-4-carbonyloxy)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 were dissolved in 30 ml of dry THF, and 0.61 g of potassium t-butoxide was added thereto at room temperature. After having been heated, the resulting product was kept heated under reflux for 3 hours. 0.61 g of potassium t-butoxide was again added thereto and further heated under reflux for 2 hours. THF was distilled off under reduced pressure, and water was added to the residual product, which was then extracted with ethyl acetate. The resulting organic layer was washed with a dilute aqueous solution of sodium hydroxide and then with water. This was dried with sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified through silica gel column chromatography to obtain 1.92 g of 3-(1-methyl-3,5-dichlorophrazol-4-yl)-2-(4-trifluoromethylphenyl)-3-(1-methyl-3,5-dichloropyrazole-4-carbonyloxy)acrylontrile from the fraction eluted with n-hexane:ethyl acetate=2:1.

Synthesis Example 6

Synthesis of 2-(4-tert-butylphenyl)-3-(1-methyl-3,5-dichloropyrazol-4-yl)-3-hydroxyacrylontrile

(Compound No. 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, and 5.00 g of 4-tert-butylbenzyl bromide was dropwise added thereto with cooling with water. After having been stirred overnight at room temperature, the resulting mixture was further stirred at 50° C. for 5 hours. After this was left to be at room temperature, water was added thereto and extracted with ether. The organic layer was washed with water, and dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residual product was purified through silica gel column chromatography to obtain 1.19 g of 4-tert-butylphenylacetonitrile was obtained from the fraction eluted 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 were dissolved in 20 ml of THF, and 1.01 g of potassium t-butoxide was added thereto with cooling with ice. After the resulting mixture was stirred overnight at room temperature, water was added thereto, acidified with diluted hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with water, and dried with sodium sulfate, and the solvent was distilled off under reduced pressure. The residual 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 having been left to be at room temperature, this was acidified with diluted hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with water, and dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residual product was purified through silica gel column chromatography to obtain 0.64 g of 2-(4-tert-butylphenyl)-3-(1-methyl-3,5-dichloropyrazol-4-yl)-3-hydroxyacrylonitrile from the fraction eluted with n-hexane:ethyl acetate=2:1.

Synthesis Example 7

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

(Compound No. IV-24)

In the same manner as above, the above-mentioned compound was synthesized (viscous liquid).

1 H-NMR (CDCl 3 , δ ppm); 1.13 (9H, s), 1.33 (9H, s), 3.98 (3H, s), 7.48 (4H, brs)

Synthesis Example 8

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

(Compound No. IV-36)

In the same manner as above, the above-mentioned compound was synthesized (vitreous, E-Z mixture).

1 H-NMR (CDCl 3 , δ ppm); 1.32 (9H, s), 3.75 (3H, s), 3.87 (3H, s), 7.49 (2H, d, J=8 Hz), 7.58 (2H, d, J=8 Hz): 75% 1.27 (9H, s), 3.88 (3H, s), 3.96 (3H, s), 7.49 (2H, d, J=8 Hz), 7.58(2H, d, J=8 Hz): 25%

Synthesis Example 9

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

(Compound No. V-40)

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

2) 6.2 g of sodium cyanide was weighed, 50 ml of dimethylsulfoxide was added thereto, and a dimethylsulfoxide solution of 16.9 g of 2-tert-butyl-4-chloromethyloxazole was dropwise added thereto, and heated on an oil bath at 65° C. for 1 hour with stirring. After the resulting product was cooled to room temperature, 150 ml of a dilute aqueous solution of sodium hydroxide was added thereto, and extracted with toluene. The organic layer was fully washed with water, and 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 tert-butoxide was suspended in 20 ml of THF, and a solution of 2.00 g of 2-tert-butyl-4-cyanomethyloxazole and 2.37 g of 3,5-dichloro-1-methylpyrazole-4-carbonyl chloride as dissolved in 10 ml of THF was dropwise added thereto with cooling with ice, and then stirred overnight at room temperature. The reaction mixture was poured into ice water, extracted with ethyl acetate, and washed with a small amount of water. After the resulting product was dried with anhydrous sodium sulfate, the solvent was evaporated out under reduced pressure. The residual product was purified through column chromatography (silica gel; n-hexane:ethyl acetate=4:1) to obtain 3.26 g of the intended compound.

Synthesis Example 10

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

(Compound No. V-44)

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

1 H-NMR (CDCl 3 , δ ppm); 1.17 (3H, t), 1.41 (9H, s), 3.98 (3H, s), 5.03 (2H, s), 8.00 (1H, s)

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 mmols) of ethyl phenylacetate and 10.7 g (50 mmols) of 3,5-dichloro-1-methylpyrazole-4-carboxylic acid chloride were dissolved in 100 ml of dry tetrahydrofuran, and 14 g (125 mmols) of potassium tert-butoxide at room temperature. The reaction mixture was stirred at room temperature for 1 hour, and 300 ml of water was added thereto, and extracted with ethyl acetate. The organic layer was washed with water and saturated saline, and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 17 g of the intended ethyl 2-phenyl-3-(3,5-dichloro-1-methylpyrazol-4-yl)-3-hydroxyacrylate.

1 H-NMR (CDCl 3 , δ ppm); 1.1-1.5 (3H, m), 3.59 (1.5H, s), 3.73 (1.5H, s), 3.95-4.45 (2H, m), 5.58 (0.5H, s), 7.0-7.35 (5H, m), 13.21 (0.5H, s)

Synthesis Example 12

Synthesis of 1-(3,5-dichloro-1-methylpyrazol-4-yl)-2-phenyl-2-bromoethanone

(Compound No. IV-90)

1) 17 g (50 mmols) of ethyl 2-phenyl-3-(3,5-dichloro-1-methylpyrazol-4-yl)-3-hydroxyacrylate was dissolved in 50 ml of 6 N HCl and 250 ml of 1,4-dioxane, and heated under reflux for 15 hours. The reaction mixture was poured into 500 ml of ice water, and precipitated crystals were taken out through filtration to obtain 8 g of the intended 1-(3,5-dichloro-1-methylpyrazol-4-yl)-2-phenylethanone as white crystals. m.p.: 94-96° C.

2) 5.38 g (20 mmols) of 1-(3,5-dichloro-1-methylpyrazol-4-yl)-2-phenylethane was dissolved in 50 ml of chloroform, and stirred at room temperature for 1 hour, and the solvent was distilled off under reduced pressure to obtain the intended 1-(3,5-dichloro-1-methylpyrazol-4-yl)-2-phenyl-2-bromoethanone 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 mmols) of 1-(3,5-dichloro-1-methylpyrazol-4-yl)-2-phenyl-bromoethane and 0.18 g (1.74 mmols) of triethylamine were dissolved in 4 ml of dry tetrahydrofuran, and 0.19 g (1.58 mmols) of pivalic acid chloride was added thereto at room temperature. After the reaction mixture was stirred for 16 hours at room temperature, 10 ml of water was added thereto, and extracted with ethyl acetate. The organic layer was washed with water and saturated saline, and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified through silica gel column chromatography to obtain 0.23 g of the intended 1-(3,4-dichloro-1-methylpyrazol-4-yl)-1-pivaloyloxy-2-phenyl-2-bromoethylene as a colorless liquid (E-Z mixture).

1 H-NMR (CDCl 3 , δ ppm); 1.05 (9H, s), 3.81 (3H, s), 7.37 (5H, m): major 1.32 (9H, s), 3.62 (3H, s), 7.24 (5H, m): minor

Synthesis Example 14

Synthesis of 1-(3,5-dichloro-1-methylpyrazol-4-yl)-2-{2-(1-methylcyclohexan-1-yl}-thiazol-4-yl-2-diethylphosphonoethanone

(Compound No. II-156)

1) 4.15 g (18.1 mmols) of 2-(1-methyl-cyclohexan-1-yl)-4-chloromethylthiazole and 3.32 g (20 mmols) of trimethyl phosphate were mixed and heated under reflux for 16 hours. The reaction mixture was cooled to room temperature, and purified through silica gel column chromatography to obtain 4.63 g of the intended diethyl {2-(1-methylcyclohexan-1-yl-thiazol-4-yl}methylphosphonate as a colorless liquid.

1 H-NMR (CDCl 3 , δ ppm); 1.25 (3H, t, J=7.2 Hz), 1.31 (3H, s), 1.1-2.3 (1OH, m), 3.33 (2H, d, J=20.4 Hz), 4.04 (4H, dd, J=7.2, 7.2 Hz), 7.01 (1H, m)

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

1 H-NMR (CDCl 3 , δ ppm); 1.23 (3H, t, J=7.2 Hz,), 1.23 (3H, s), 1.1-2.3 (1OH, m), 3.79 (3H, s), 4.09 (2H, dd, J=7.2, 7.2 Hz), 5.90 (1H, d, J=22.8 Hz), 7.43 (1H, m)

Synthesis Example 15

Synthesis of allyl 2-{3-(2,6-difluorophenyl)pyrazol-1-yl}-3-(5-chloro-1-methyl-3-trifluoromethylpyrazol-4-yl)-3-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 acetate and diluted hydrochloric acid added thereto at room temperature. The organic layer was dried over anhydrous magnesium sulfate and concentrated, and the resulting concentrate was purified through silica gel column chromatography (chloroform) to obtain allyl 2-{3-(2,6-difluorophenyl) pyrazol-1-yl}acetate (1.5 g).

1 H-NMR (CDCl 3 , δ ppm); 4.70 (2H, d, J=6.0 Hz), 5.10 (2H, s), 5.30-5.60 (2H, m), 5.70-6.40 (1H, m), 6.50-7.80 (5H, m)

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

1 H-NMR (CDCl 3 , δ ppm): 3.95 (3H, s), 4.80 (2H, d, J=6.0 Hz), 5.20-5.60 (2H, m), 5.60-6.40 (1H, m), 6.45-7.90 (6H, m)

Synthesis Example 16

Synthesis of 2-bromo-2-{3-(2,6-difluorophenyl) pyrazol-1-yl}-1-(5-chloro-1-methyl-3-trifluoromethylpyrazol-4-yl)-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 for 5 minutes at room temperature in a nitrogen atmosphere. A THF (5 mL) solution of Compound I-133 (0.32 g) was added thereto and refluxed for 1 hour. The reaction mixture was left to be at room temperature, and concentrated, and the resulting concentrate was purified through silica gel column chromatography (chloroform) and recrystallization (chloroform-diisopropyl ether) to obtain 2-{3-(2,6-difluorophenyl)pyrazol-1-yl}-3-(5-chloro-1-methyl-3-trifluoromethylpyrazol-4-yl)ethan-1-one (0.1 g). m.p.: 152-154° C.

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

Synthesis Example 17

Synthesis of 2-bromo-2-{3-(2,6-difluorophenyl) pyrazol-1-yl}-1-(5-chloro-1-methyl-3-trifluoromethylpyrazol-4-yl)-1-pivaloyloxyethylene

(Compound No. I-135)

Triethylamine (0.3 g) and pivalic acid chloride (0.23 g) were added in that order to a chloroform (25 ml) solution of Compound No. I-134 (0.47 g) at 0° C., and stirred at room temperature for 1 hour. The resulting product was extracted with water and chloroform. The organic layer was dried with anhydrous magnesium sulfate, concentrated, and purified through silica gel column chromatography (chloroform) to obtain the intended product, Compound No. I-135 (0.4 g).

1 H-NMR (CDCl 3 , δ ppm); 1.25 (9H, s), 3.90 (3H, s), 6.55-7.80 (5H, m)

In accordance with the above-mentioned reaction schemes or Examples, various compounds of the present invention were produced, of which the structure and the melting point are shown in Table 15 to Table 19 below. Unless otherwise specifically indicated, the compounds shown in these are in the form of a mixture of E-form and Z-form. The abbreviations in these have the same meanings as those mentioned above.

Formulation Examples

Now, Formulation Examples of pesticides comprising the compounds of the present invention as the active ingredient are shown below, which, however, are not intended to restrict the scope of the invention. In the following Formulation Examples, “part” or “parts” are by weight.

The above-mentioned components were homogeneously mixed and ground to form a wettable powder.

The above-mentioned components were homogeneously mixed to form an emulsion.

The above-mentioned components were homogeneously mixed to prepare a flowable.

The above-mentioned components were homogeneously mixed and finely ground to form a dry flowable.

The above-mentioned components were homogeneously mixed and ground, to which was added a small amount of water, stirred, mixed and kneaded. The resulting mixture was granulated and dried into granules, using an extrusion granulator.

The above-mentioned components were homogeneously mixed and ground to form a dust.

Upon use, the wettable powder, emulsion, flowable and dry flowable are diluted from 50 to 20000 times with water, and applied in an amount of from 0.005 to 50 kg/ha in terms of the active ingredient.

Now, Formulation Examples of agents for preventing the attachment of aquatic organisms of the present invention are shown below, which, however, are not intended to restrict the scope of the invention.

The above-mentioned components were homogeneously mixed to form an agent for preventing the attachment of aquatic organisms of the invention. This agent can be used as a coating paint.

The above-mentioned components were homogeneously mixed to form an agent for preventing the attachment of aquatic organisms of the invention. This agent can be used as a coating paint.

The above-mentioned components were homogeneously mixed to form an agent for preventing the attachment of aquatic organisms the invention. This agent can be used as a coating paint.

The above-mentioned components were homogeneously mixed to form an agent for preventing the attachment of aquatic organisms of the invention. This agent can be used as a coating paint.

Now, the following Test Examples are to demonstrate the usefulness of the compounds of the present invention as pesticides.

Test Example 1

Insecticidal Test for Brown Rice Planthopper (Nilaparvata lugens Stal)

A 5% emulsion (or 25% wettable powder) of a compound of the present invention was diluted with water containing a spreading agent to give a 500 ppm solution of the compound.

The stems and leaves of rice-plants in 1/20,000 are pot were sufficiently applied with the resulting solution. After the thus-applied chemical solution was dried in air, each pot was covered with a cylindrical cover. Ten (10) second instar nymphae of brown rice planthoppers (Nilaparvata lugens) were released in each pot. After having been thus covered, the pots were stored in a thermostatic chamber. After 6 days passed, the insects in each pot were observed, and the mortality thereof was determined according to the following equation. Each compound was tested in that manner for two groups of pots.

Mortality (%)=[number of insect killed/(number of insect killed+number of living insect)]×100

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

Compounds of the invention: Nos. I-2, I-18, I-19, I-23, I-30, I-31, I-32, I-35, I-39, I-42, I-44, I-58, I-59, I-62, I-63, I-70, I-72, I-80, I-106, I-114, I-123, I-137, II-1, II-2, II-3, II-5, II-6, II-12, II-15, II-23, II-25, II-26, II-28, II-33, II-34, II-36, II-37, II-38, II-39, II-43, II-44, II-46, II-53, II-54, II-55, II-61, II-66, II-73, II-74, II-75, II-76, II-80, II-83, II-84, II-85, II-86, II-87, II-88, II-89, II-91, II-92, II-93, II-97, II-98, II-111, II-114, II-116, II-134, II-136, II-137, II-154, II-155, II-159, III-1, III-2, III-4, III-6, III-15, III-16, III-17, III-18, III-19, III-21, IV-48, IV-58, V-2, V-12, V-13, V-28, V-48, V-49, V-51, V-53, V-54, V-55, V-56, V-57, V-59, V-60.

Test Example 2

Insecticidal Test for Green Rice Leafhoppers (Nephotettix cincticeps Uhler)

The stems and leaves of plants was dipped in a 500 ppm emulsion of a compound of the invention for about 10 seconds. The thus-treated stems and leaves were put into glass cylinders, into which were released adults of green rice leafhoppers (Nephotettix cincticeps) that were resistant to organic phosphorous insecticides. Each glass cylinder was covered with a perforated cover, and stored in a thermostatic chamber at 25° C. After 6 days passed, the insects in each cylinder were observed, and the mortality of the insects was determined according ot the sme equation as in Test Example 1. Each compound was tested in that manner for two groups of cylinders. In this test, the following compounds exhibited morality of 80% or more.

Compounds of the invention: Nos. I-1, I-2, I-4, I-5, I-8, I-9, I-10, I-19, I-24, I-29, I-30, I-31, I-32, I-33, I-34, I-35, I-36, I-39, I-40, I-41, I-42, I-43, I-44, I-47, I-53, I-54, I-55, I-56, I-57, I-58, I-59, I-62, I-63, I-69, I-70, I-71, I-72, I-74, I-79, I-80, I-81, I-115, I-121, I-125, I-127, I-137, II-1, II-2, II-3, II-5, II-6, II-7, II-9, II-10, II-11, II-12, II-13, II-15, II-23, II-26, II-28, II-33, II-34, II-36, II-38, II-37, II-43, II-46, II-49, II-52, II-54, II-55, II-63, II-64, II-65, II-66, II-67, II-68, II-69, II-73, II-74, II-75, II-76, II-77, II-78, II-79, II-80, II-81, II-83, II-84, II-85, II-86, II-87, II-88, II-89, II-91, II-92, II-93, II-97, II-98, II-99, II-107, II-111, II-116, II-117, II-130, II-131, II-132, II-134, II-136, II-137, II-142, II-145, II-153, II-154, II-1, III-2, III-3, III-4, III-5, III-6, III-13, III-15, III-16, III-17, III-18, III-19, III-20, III-21, IV-32, IV-58, V-2, V-12, V-13, V-14, V-38, V-41, V-43, V-48, V-49, V-51, V-53, V-54, V-55, V-56, V-57, V-59, V-60, V-75.

Test Example 3

Insecticidal Test for Green Peach Aphids (Myzus persicae Sulzer)

Moistured filter paper was placed in each laboratory glass dish having an inner diameter of 3 cm, and a leaf cabbage having the same diameter as that of the dish was put on the filter paper. Four female, apterous adults of green peach aphids (Myzus persicae) were put on the cabbage leaf. Following day, a chemical sample (2.5 mg/cm 2 ) was sprayed over the dishes, using a rotary sprinkler. The chemical solution herein was prepared by diluting a 5% emulsion (or 25% wettable powder) of a compound of the invention to 500 ppm with water containing a spreading agent. After 6 days passed, the insects in each cylinder were observed, and mortality of the insects (larvae and adults) was determined according to the following equation. Each compound was tested in that manner for two groups of dishes.

Mortality (%)=[number of insect killed/(number of insect killed+number of living insect)]×100

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

Compounds of the invention: Nos. I-1, I-2, I-3, I-4, I-5, I-7, I-8, I-10, I-11, I-12, I-13, I-14, I-16, I-17, I-18, I-19, I-21, I-22, I-23, I-24, I-25, I-26, I-27, I-28, I-29, I-30, I-31 I-32, I-33, I-34, I-35, I-36, I-37, I-38, I-40, I-41, I-42, I-43, I-44, I-45, I-46, I-47, I-48, I-51, I-52, I-53, I-54, I-55, I-56, I-57, I-58, I-59, I-62, I-63, I-69, I-70, I-71, I-72, I-73, I-74, I-76, I-77, I-78, I-79, I-80, I-81, I-84, I-85, I-86, I-89, I-90, I-92, I-96, I-97, I-104, I-108, I-125, I-136, I-137, I-138, II-2, II-3, II-5, II-6, II-7, II-8, II-9, II-10, II-11, II-12, II-15, II-16, II-17, II-23, II-24, II-24, II-25, II-26, II-27, II-28, II-33, II-34, II-35, II-36, II-37, II-38, II-39, II-43, II-44, II-50, II-52, II-53, II-54, II-55, II-58, II-60, II-63, II-64, II-65, II-66, II-68, II-69, II-70, II-71, II-73, II-74, II-75, II-76, II-78, II-79, II-83, II-84, II-85, II-86, II-87, II-88, II-89, II-90, II-91, II-92, II-93, II-97, II-98, II-99, II-101, II-102, II-105, II-107, II-111, II-116, II-117, II-118, II-121, II-130, II-131, II-132, II-133, II-134, II-136, II-137, II-138, II-140, II-141, II-142, II-151, II-153, II-154, II-159, II-160, III-1, III-2, III-3, III-4, III-5, III-6, III-15, III-16, III-17, III-18, III-19, III-20, III-21, IV-10, IV-11, IV-21, IV-23, IV-45, V-1, V-2, V-10, V-11, V-12, V-13, V-14, V-28, V-31, V-32, V-41, V-45, V-48, V-49, V-50, V-51, V-52, V-53, V-54, V-55, V-56, V-57, V-59, V-60, V-73, V-75, VII-1, VII-2, VII-3, VII-4, VII-5, VII-6, VII-7, VII-8, VII-9, VII-10, VII-11, VII-12, VII-13, VII-14, VII-15, VII-16, VII-17, VII-18, VII-19, VII-20, VII-21, VII-22, VII-23, VII-24, VII-25, VII-26, VII-27, VII-28, VII-29, VII-30, VII-31, VII-32, VII-33, VII-34, VII-35, VII-36, VII-37, VII-38, VII-39, VII-40, VII-41, VII-42, VII-43, VII-44, VII-45, VIII-12, VIII-32, VIII-42, VIII-47, VIII-49, VIII-55, VIII-57, VIII-58, VIII-61, VIII-64, VIII-65, VIII-67, VIII-85.

Test Example 4

Insecticidal Test for Diamond Back Moth (Plutella xylostella Linne)

The leaves of cabbage were dipped in a 500 ppm aqueous emulsion of a compound of the invention for about 10 seconds. After having been dried in air, the thus-treated leaves were put into laboratory dishes. Ten (10) second larvae of diamond back moth (Plutella xylostella) were released in each dish. Each dish was covered with a perforated cover, and stored in a thermostatic chamber at 25° C. After 6 days passed, the insects in each dish were observed, and mortality of the insects was obtained according to the same equation as in Test Example 1. Each compound was tested in that manner for two groups of dishes. In this test, the following compounds exhibited mortality of 80% or more.

Compounds of the invention: Nos. I-1, I-2, I-4, I-5, I-6, I-8, I-9, I-10, I-13, I-18, I-19, I-29, I-30, I-31, I-33, I-34, I-35, I-36, I-38, I-39, I-40, I-41, I-43, I-44, I-45, I-46, I-47, I-51, I-52, I-53, I-56, I-57, I-58, I-59, I-62, I-63, I-70, I-71, I-72, I-73, I-74, I-76, I-77, I-78, I-79, I-80, I-81, I-84, I-86, I-89, I-96, I-97, I-99, I-104, I-106, I-114, I-125, I-137, II-1, II-2, II-5, II-6, II-7, II-8, II-9, II-10, II-11, II-12, II-13, II-15, II-17, II-23, II-24, II-25, II-26, II-27, II-28, II-33, II-34, II-35, II-36, II-37, II-38, II-39, II-40, II-41, II-42, II-43, II-54, II-55, II-58, II-60, II-61, II-62, II-63, II-64, II-65, II-66, II-67, II-68, II-69, II-70, II-71, II-72, II-73, II-74, II-75, II-76, II-77, II-78, II-79, II-80, II-81, II-83, II-84, II-85, II-86, II-87, II-88, II-89, II-90, II-91, II-92, II-93, II-94, II-97, II-98, II-99, II-100, II-101, II-105, II-106, II-107, II-108, II-109, II-110, II-111, II-116, II-117, II-118, II-121, II-122, II-155, II-159, II-161, II-1, III-2, III-3, III-4, III-5, III-6, III-7, III-9, III-10, III-11, III-13, III-14, III-15, III-16, III-17, III-18, III-19, III-20, III-21, IV-7, IV-8, IV-29, IV-47, IV-53, IV-58, V-1, V-2, V-11, V-12, V-13, V-29, V-37, V-41, V-43, V-46, V-48, V-50, V-51, V-52, V-53, V-54, V-55, V-56, V-57, V-58, V-59, V-60, V-64, V-75.

Test Example 5

Insecticidal Test for Cucurbit Leaf Beetles (Aulacophora femoralis Motschulsky)

A 5% emulsion (or 25% wettable powder) of a compound of the present invention was diluted with water containing a spreading agent to give a 500 ppm solution of the compound. The leaves of cucumbers were dipped in this chemical solution for about 10 seconds, dried in air, and put into a laboratory dish. Ten (10) second instar nymphae of cucur-bit leaf beetles (Aulacophora femoralis) were released in each dish. Each dish was covered with a cover, and stored in a thermostatic chamber at 25° C. After 6 days passed, the insects in each dish were observed, and mortality of the insects was determined according to the same equation as in Test Example 1. Each compound was tested in that manner for two groups of dishes.

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

Compounds of the invention: Nos. I-1, I-2, I-4, I-6, I-8, I-9, I-10, I-11, I-12, I-13, I-29, I-30, I-31, I-32, I-33, I-34, I-35, I-39, I-40, I-41, I-43, I-44, I-46, I-53, I-54, I-55, I-56, I-57, I-58, I-59, I-61, I-62, I-63, I-69, I-70, I-71, I-72, I-74, I-76, IU-77, I-78, I-79, I-80, I-81, I-82, I-83, I-92, I-101, I-103, I-104, I-108, I-109, I-124, I-127, I-128, II-1, II-6, II-7, II-8, II-9, II-10, II-11, II-12, II-13, II-14, II-15, II-16, II-17, II-23, II-24, II-25, II-26, II-27, II-28, II-33, II-34, II-35, II-36, II-37, II-38, II-39, II-41, II-42, II-43, II-47, II-50, II-53, II-54, II-55, II-57, II-58, II-61, II-62, II-63, II-65, II-66, II-99, II-101, II-102, II-104, II-105, II-106, II-107, II-108, II-109, II-110, II-114, II-122, II-124, II-125, II-131, II-132, II-133, II-134, II-136, II-137, II-139, II-140, II-141, II-142, II-153, II-154, III-1, III-2, III-3, II-4, III-5, III-6, III-9, III-10, III-11, III-12, III-14, III-15, III-16, III-17, III-20, IV-6, IV-13, IV-33, IV-39, IV-56, IV-60, IV-61, IV-72, IV-82, V-1, V-2, V-11, V-12, V-13, V-17, V-22, V-26, V-27, V-29, V-37, V-40, V-42, V-48, V-49, V-50, V-51, V-52, V-54, V-55, V-57, V-59, V-60, V-61, V-64, V-75.

Test Example 6

Acaricidal Test for Two-spotted Spider Mites (Tetranychus urticae Koch)

The leaves of kidney bean plants were punched into 3 cm-diameter discs, using a leaf punch, and put onto moistured filter paper in a 7 cm-diameter styrol cup. Ten (10) larvae of two-spotted spider mites (Tetranychus urticae) were put to each leaf. A 5% emulsion (or 25% wettable powder) of a compound of the invention was diluted with water containing a spreading agent to give a 500 ppm solution of the compound. The solution was sprayed over each cup in an amount of 2 ml/cup, using a rotary sprinkler, and the cups were stored in a thermostatic chamber at 25° C. After 96 hours passed, the mites in each cup were observed, and mortality of the mites was determined according to the same equation as in Test Example 1. Each compound was tested in that manner for two groups of cups.

In this test, the following compounds exhibited the mites at a percentage of 80% or more.

Compounds of the invention: Nos. I-1, I-2, I-3, I-4, I-5, I-7, I-8, I-9, I-10, I-12, I-13, I-19, I-24, I-25, I-26, I-27, I-28, I-29, I-30, I-31, I-32, I-33, I-34, I-35, I-36, I-38, I-40, I-41, I-42, I-43, I-44, I-45, I-46, I-47, I-48, I-50, I-51, I-52, I-55, I-56, I-57, I-58, I-59, I-60, I-61, I-62, I-63, I-70, I-71, I-72, I-74, I-76, I-80, I-94, I-95, I-96, I-97, I-99, I-101, I-102, I-103, I-104, I-105, I-106, I-108, I-109, I-110, I-111, I-112, I-113, I-114, I-115, I-117, I-118, I-119, I-122, I-123, I-124, I-125, I-126, I-127, I-128, I-137, II-2, II-3, II-5, II-6, II-7, II-8, II-9, II-10, II-11, II-12, II-13, II-15, II-16, II-17, II-23, II-25, II-26, II-27, II-28, II-33, II-34, II-35, II-36, II-37, II-38, II-39, II-40, II-41, II-42, II-43, II-45, II-46, II-47, II-48, II-50, II-52, II-53, II-54, II-55, II-58, II-59, II-60, II-61, II-63, II-64, II-65, II-66, II-67, II-68, II-69, II-70, II-71, II-72, II-73, II-74, II-75, II-76, II-77, II-78, II-79, II-80, II-81, II-83, II-84, II-85, II-86, II-87, II-88, II-89, II-90, II-91, II-92, II-93, II-95, II-97, II-98, II-99, II-101, II-102, II-103, II-105, II-106, II-107, II-108, II-109, II-110, II-111, II-116, II-117, II-118, II-133, II-134, II-136, II-137, II-151, II-153, II-154, II-155, II-159, II-160, II-161, II-173, III-3, III-4, III-5, III-6, III-7, III-9, III-10, III-11, III-12, III-15, III-17, III-18, III-19, III-21, IV-1, IV-2, IV-3, IV-4, IV-5, IV-7, IV-10, IV-11, IV-12, IV-13, IV-14, IV-16, IV-17, IV-18, IV-19, IV-20, IV-21, IV-22, IV-24, IV-25, IV-26, IV-28, IV-29, IV-33, IV-35, IV-36, IV-39, IV-40, IV-41, IV-42, IV-43, IV-44, IV-45, IV-46, IV-47, IV-48, IV-49, IV-50, IV-51, IV-54, IV-55, IV-56, IV-58, IV-59, IV-60, IV-61, IV-62, IV-63, IV-64, IV-65, IV-66, IV-67, IV-68, IV-69, IV-70, IV-71, IV-72, IV-74, IV-75, IV-76, IV-79, IV-80, IV-82, IV-94, IV-95, IV-96, IV-99, IV-100, IV-101, IV-102, IV-109, IV-110, IV-111, IV-112, V-1, V-2, V-3, V-4, V-5, V-6, V-7, V-8, V-10, V-11, V-12, V-13, V-14, V-15, V-16, V-17, V-19, V-23, V-24, V-25, V-26, V-28, V-31, V-36, V-37, V-38, V-40, V-41, V-42, V-43, V-44, V-46, V-47, V-48, V-59, V-60, V-73, V-75, VI-1, VI-2, VI-3, VI-4, VI-5, VI-6, VI-7, VI-87, VI-9, VI-10, VI-11, VI-12, VI-13, VI-14, VI-15, VI-16, VI-17, VI-18, VI-19, VI-20, VI-21, VI-22, VI-23, VI-24, VI-25, VI-29, VI-30, VI-31, VI-32, VI-33, VI-34, VI-35, VI-36, VI-37, VI-38, VI-39, VI-40, VI-41, VI-42, VI-43, VI-44, VI-45, VI-46, VI-47, VI-48, VI-49, VI-50, VI-51, VI-52, VII-1, VIII-2, VIII-4, VIII-6, VIII-7, VIII-8, VIII-9, VIII-10, VIII-13, VIII-14, VIII-15, VIII-16, VIII-17, VIII-18, VIII-19, VIII-20, VIII-21, VIII-22, VIII-23, VIII-24, VIII-26, VIII-27, VIII-28, VIII-29, VIII-30, VIII-31, VIII-33, VIII-34, VIII-35, VIII-36, VIII-37, VIII-38, VIII-39, VIII-40, VIII-41, VIII-43, VIII-44, VIII-45, VIII-46, VIII-48, VIII-50, VIII-51, VIII-52, VIII-53, VIII-54, VIII-56, VIII-59, VIII-60, VIII-63, VIII-66, VIII-69, VIII-70, VIII-71, VIII-72, VIII-73, VIII-74, VIII-75, VIII-76, VIII-77, VIII-78, VIII-81, VIII-82, VIII-83, VIII-84, VIII-86, VIII-87, VIII-89, VIII-90, VIII-91, VIII-92, VIII-93.

Test Example 7

A chemical solution obtained by diluting an emulsion of a compound of the invention to 500 ppm with water was sprayed on wheat plants (Norin No. 61) grown to 1.5- to 2.0-leaf in a pot having a diameter of 5.5 cm-diameter at a dose of 20 ml/pot using a spraygun.

The following day, a spore suspension (2×10 5 spore/ml) of leaf rust (brown rust) (Puccinia recondite) was sprayed over the plant-pots were placed overnight in an inoculation box having a temperature of 25° C. and a humidity of 95% or more. Then, the pots were put in a green house. After 7 days of the inoculation, a ratio of an infected and spored area formed to the leaf inoculated was measured, and a preventive value was calculated according to the following equation.

Preventive value=[1−(infected and spotted area ratio in treated region/infected and spotted area ratio in untreated region)]×100

In this test, the following compounds had an protective value of from 70 to 100.

Compounds of the invention: Nos. I-9, I-108, I-127, I-128, II-14, II-15, IV-2, IV-7, V-15, V-10.

With the long-term use of insecticides and microbicides, recently, some pests have become resistant to chemicals and are often difficult to exterminate with conventional insecticides and microbicides. In addition, some insecticides are highly toxic and are prone to remain long, without being decomposed, to destroy the ecosystem. Accordingly, the present invention provides novel, non-toxic and non-persistent insecticides and fungicides, and provides agents for preventing the attachment of aquatic organisms having few influences on the ecosystem and causing little secondary pollution.