JP2003055350A - Pyridazinones and pesticides containing them as an active ingredient - Google Patents

Abstract

(57) [Abstract] [Problem] To provide a substance useful for controlling insects, mites and other pests in agriculture, forestry, fisheries, animal husbandry, public health, and the like. SOLUTION: A pyridazinone represented by the following general formula (I) and a pesticidal composition containing the same as an active ingredient. (Wherein, R ¹ is a C ₁ -C ₅ alkyl group, R ² is a hydrogen atom · C ₁ -C ₃ alkyl group, R ³ is a C ₁ -C ₅ alkyl group, C ₁ -C ₅ A haloalkyl group, a C ₁ -C ₅ alkoxy group, a C ₁ -C ₅ haloalkoxy group, and a halogen atom represented by R
⁴ is an alkyl group of C ₁ -C _8, a haloalkyl group of C ₁ -C _5, alkoxy groups of C ₁ -C _5, a haloalkoxy group of C ₁ -C _5, etc., m is an integer of 0 to 4, n is an integer of 0 to 5, X
Represents a halogen atom. )

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a novel pyridazinone and a pest control agent containing the pyridazinone as an active ingredient. The novel pyridazinones of the present invention are useful for controlling various pests, especially insects and mites.

[0002]

In the field of agriculture and horticulture, various insecticides for controlling various pests have been developed and put into practical use. However, conventionally used agricultural and horticultural insecticides are not always satisfactory in terms of insecticidal effect, insecticidal spectrum, residual effect and the like. Moreover, it cannot be said that the demands such as the number of times of application and the amount of applied drug have been satisfied.

Another problem is the appearance of pests that have acquired resistance to conventional agricultural chemicals. For example, vegetables,
In the cultivation of fruit trees, flowers, tea, wheat and rice,
Various pests that have acquired resistance to various types of pesticides, for example, carbamate-based, pyrethroid-based, benzoylurea-based, organochlorine-based, organophosphorus-based pesticides, etc. are appearing in various places, and these pests are resistant to these pests. The control of various pests caused by it has become difficult year by year.

[0004] Development of new insecticides showing a sufficient control effect with a low dose even against various insect pests that have acquired resistance to conventional general-purpose agricultural and horticultural insecticides and having little adverse effect on the environment has been earnestly desired. ing. As for acaricides as well, it is expected to develop a highly safe acaricide that exhibits an excellent control effect even on mites that are conventionally resistant to general-purpose acaricides.

In response to these demands, various new neutralizing agents and acaricides have been proposed, but they are not always able to meet the above demands. JP-A 61-10561 and JP-A 3-56466 describe that pyridazinones have insecticidal and acaricidal activity. However,
No. 61-10561 discloses only a compound in which a pyridazinone ring is bonded to a benzyl group via a sulfur atom or an oxygen atom, and a compound in which a pyridazinone ring is bonded to a phenylbenzyl group via a nitrogen atom is not described at all. Absent.

Japanese Unexamined Patent Publication (Kokai) No. 3-56466 describes pyridazinones having a similar structure, and the substituent on the benzene ring is a fluoroalkoxyalkoxy group. Is not listed. Regarding the compound in which the pyridazinone ring and the benzyl group are bonded via the nitrogen atom, only the following compound is described, but the insecticidal and acaricidal effect of this compound is not described.

[0007]

[Chemical 2]

5-Benzylaminopyridazinones similar to those of the present invention are disclosed in Japanese Examined Patent Publication No. 6-76390, Heterocycles, Vol. 36, No. 4, 785.
Page (1993). Japanese Examined Patent Publication No. 6-76390 relates to a pyridazinone compound having an antiallergic effect, in which the 2-position of pyridazinone is a hydrogen atom, a methyl group, an alkenyl group (having 3 to 6 carbon atoms), a cycloalkyl group (having 5 or 6 carbon atoms), and benzyl. Group, phenyl group and the like, 4-position is a chlorine atom or bromine atom, the substituent on the benzene ring is a compound such as an alkoxy group, but the 2-position of pyridazinone is C
_There is no description of compounds having an alkyl group of _{3 to} C ₅ . Of course, the use as an agricultural chemical such as an insecticide and an acaricide is not described. In Heterocycles, Vol. 36, No. 4, p. 785 (1993), the 2-position of pyridazinone is a methyl group, a phenyl group, the 4-position is a chlorine atom or a bromine atom, and the substituent on the benzene ring is a benzyl group such as a methoxy group. There is a description of a compound in which the α-position is a hydrogen atom or a methyl group, but only the reaction conditions between the pyridazinones and benzylamines, and the mechanism are considered.
Its use as a pesticide is not described.

[0009]

An object of the present invention is to provide a new substance useful for controlling pests such as insects and mites, and particularly to various pests resistant to conventional insecticides. It is also intended to provide a highly safe substance that exhibits a high control effect, is effective even at a low dose, and has reduced problems such as residual toxicity and environmental pollution.

[0010]

Means for Solving the Problems As a result of intensive studies to solve the above problems, the inventors of the present invention found a novel pyridazinone compound satisfying the above characteristics, and completed the present invention. That is, the gist of the present invention is the following general formula (I)

[0011]

[Chemical 3]

(Wherein R ¹ represents a C ₁ -C ₅ alkyl group, R ² represents a hydrogen atom or a C ₁ -C ₃ alkyl group, R ³ represents a C ₁ -C ₅ alkyl group, C ₁ -C haloalkyl group _5, C ₁ -C alkoxy group _5, .R ⁴ .m is to an integer of 0 to 4 indicating the haloalkoxy group, or a halogen atom C ₁ -C ₅ is C ₁ -C ₈ alkyl groups, C ₁ -C ₅ haloalkyl groups, C ₁ -C ₅ alkoxy groups, C ₁ -C ₅ haloalkoxy groups, C ₁ -C ₅ alkylthio groups, C ₁ -C ₅ alkylsulfinyl Group, a C ₁ -C ₅ alkylsulfonyl group or a halogen atom, n represents an integer of 0 to 5, X represents a halogen atom), and the pyridazinones are contained as an active ingredient. Pest control agent.

[0013]

BEST MODE FOR CARRYING OUT THE INVENTION The present invention will be described in detail below.
In the pyridazinone compound of the present invention represented by the general formula (I), the substituent R ¹ is a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group. , Pentyl group, 2-methylbutyl group, 3-methylbutyl group, isopentyl group, 2-ethylpropyl group, neopentyl group, 2,2-dimethylpropyl group,
A C ₁ -C ₅ linear or branched alkyl group such as a 2-methylisobutyl group is shown. As R ¹ , a C ₃ -C ₄ branched chain alkyl group is preferable, and a tert-butyl group is particularly preferable.
R ² is a hydrogen atom; methyl group, ethyl group, propyl group,
A C ₁ -C ₃ linear or branched alkyl group such as an isopropyl group is shown. R ² is preferably a hydrogen atom. R ³
Is a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-
C _{1 to} C ₅ such as butyl group, n-pentyl group, 2-methylbutyl group, 3-methylbutyl group, isopentyl group, 2-ethylpropyl group, neopentyl group, 2,2-dimethylpropyl group, 2-methylisobutyl group A straight chain or branched chain alkyl group; fluoromethyl group, chloromethyl group, bromomethyl group, difluoromethyl group, difluoroethyl group, trifluoromethyl group, trichloromethyl group, tribromomethyl group,
2-fluoroethyl group, 2,2,2-trifluoroethyl group, 1-
(Trifluoromethyl) ethyl group, 1,1,2,3,3,3-hexafluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, 2,2,3,3-tetrafluoro Propyl group, 2,2,3,3,4,
4,4 heptafluorobutyl group, 2,2,3,3,4,4,5,5,5 straight or branched chain haloalkyl group having C ₁ -C _5, such as nonafluorobutyl pentyl group; methoxy group, Ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, sec-butoxy group, isobutoxy group, tert-butoxy group, n-pentoxy group, 2-methylbutoxy group, 3-methylbutoxy group, isopentoxy group, 2-ethyl-proto alkoxy group, neopentoxy group, 2,2-dimethyl-propoxy group, 2-methyl-isobutoxy group, a straight chain or branched chain alkoxy group of C ₁ -C ₅ and the like; difluoromethoxy group, a trifluoromethoxy group, Fluoromethoxy group, trichloromethoxy group, tribromomethoxy group, 2-fluoroethoxy group, 2,2,2-trifluoroethoxy group, 2,2,2-trichloroethoxy group, 1- (trifluoromethyl) ethoxy group, 1,1,2,3,3,3-hexaful Oropropoxy group, 2,2,3,3,3-pentafluoropropoxy group, 2,2,3,3-tetrafluoropropoxy group, 2,2,3,3,4,
C ₁ -C ₅ straight or branched chain haloalkoxy group such as 4,4-heptafluorobutoxy group and 2,2,3,3,4,4,5,5,5-nonafluoropentoxy group; fluorine; A halogen atom such as an atom, a chlorine atom, a bromine atom and an iodine atom is shown. Of these, a methyl group or a halogen atom is preferable as the substituent R ³ . Further, m is an integer of 0 to 4, but a case where it is 0 is also preferable. X represents a halogen atom such as a fluorine atom, a chlorine atom and a bromine atom. As X, a chlorine atom and a bromine atom are preferable, and a chlorine atom is particularly preferable. The substituent R ⁴ is methyl group, ethyl group, n-propyl group, isopropyl group, cyclopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group, n-pentyl group, 2-methylbutyl group. Group, 3-methylbutyl group, isopentyl group, 2-ethylpropyl group, neopentyl group, 2,2-dimethylpropyl group, 2-
Methylisobutyl group, n-hexyl group, n-heptyl group, n-
Straight or branched chain alkyl group of C ₁ -C _8, such as octyl group, fluoromethyl group, chloromethyl group, bromomethyl group, difluoromethyl group, difluoroethyl group, a trifluoromethyl group, trichloromethyl group, tribromomethyl group , 2-fluoroethyl group, 2,2,2-trifluoroethyl group, 1- (trifluoromethyl) ethyl group, 1,1,2,3,3,3-
Hexafluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, 2,2,3,3-tetrafluoropropyl group, 2,2,
3,3,4,4,4-heptafluorobutyl group, 2,2,3,3,4,4,5,5,
C ₁ -C ₅ linear or branched haloalkyl group such as 5-nonafluoropentyl group; methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, sec-butoxy group, isobutoxy group, tert-butoxy group, n-pentoxy group, 2-methylbutoxy group, 3-methylbutoxy group, isopentoxy group, 2-ethylpropoxy group, neopentoxy group, 2,2-dimethylpropoxy group, 2-methylisobutoxy group, n- hexyloxy group, n- heptyloxy group, n- octyl straight or branched chain alkoxy group of C ₁ -C _8, such as a group; a difluoromethoxy group, a trifluoromethoxy group, fluoromethoxy group, trichloromethoxy group, Tribromomethoxy group, 2-fluoroethoxy group, 2,2,2-trifluoroethoxy group, 2,2,2-trichloroethoxy group, 1-
(Trifluoromethyl) ethoxy group 1,1,2,3,3,3-hexafluoropropoxy group, 2,2,3,3,3-pentafluoropropoxy group, 2,2,3,3-tetrafluoropropoxy group Base, 2,2,
C ₁ -C ₅ linear or branched haloalkoxy group such as 3,3,4,4,4-heptafluorobutoxy group; methylthio group, ethylthio group, propylthio group, isopropylthio group, butylthio group, sec-butylthio group Group, isobutylthio group, tert
-Butylthio group, pentylthio group, 2-methylbutylthio group, 3-methylbutylthio group, isopentylthio group, 2-ethylpropylthio group, neopentylthio group, 2,2-dimethylpropylthio group, 2-methyl C ₁ such as isobutylthio group
To C ₅ straight or branched chain alkylthio group; methylsulfinyl group, ethylsulfinyl group, propylsulfinyl group, isopropylsulfinyl group, butylsulfinyl group, sec-butylsulfinyl group, isobutylsulfinyl group, tert-butylsulfinyl group, pentylsulfinyl group Group, 2-methylbutylsulfinyl group, 3-methylbutylsulfinyl group, isopentylsulfinyl group,
C ₁ -C ₅ linear or branched alkylsulfinyl group such as 2-ethylpropylsulfinyl group, neopentylsulfinyl group, 2,2-dimethylpropylsulfinyl group, 2-methylisobutylsulfinyl group; methylsulfonyl group, ethylsulfonyl group Group, propylsulfonyl group, isopropylsulfonyl group, butylsulfonyl group, sec-butylsulfonyl group, isobutylsulfonyl group, tert-butylsulfonyl group, pentylsulfonyl group, 2-methylbutylsulfonyl group, 3-methylbutylsulfonyl group, isopentyl Sulfonyl group, 2-ethylpropylsulfonyl group,
C ₁ -such as neopentylsulfonyl group, 2,2-dimethylpropylsulfonyl group, 2-methylisobutylsulfonyl group, etc.
A C ₅ straight chain or branched chain alkylsulfonyl group; showing a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. R ⁴ is preferably a trifluoromethoxy group or a difluoromethoxy group. Further, the substitution position is preferably 4-position.

The compound of the present invention represented by the general formula (I) is a novel compound and can be produced, for example, according to the following reaction formula.

[0015]

[Chemical 4]

(In the above formula, R ¹ , R ² , R ³ , R ⁴ , X, m
And n are as defined in the general formula (I). ) That is, pyridazinones (II) and benzylamines (III)
Is reacted in the presence or absence of a base, preferably with a solvent, at 10 to 200 ° C, preferably 100 to 150 ° C. The solvent is not particularly limited as long as it does not directly participate in this reaction, and examples thereof include aromatic hydrocarbons such as benzene, toluene and xylene; ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone; halogens such as chloroform and dichloromethane. Hydrocarbons; water; esters such as ethyl acetate and methyl acetate; or polar solvents such as tetrahydrofuran, acetonitrile, dioxane, N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide, pyridine, etc. . Examples of the base include alkali metal hydrides such as sodium hydride; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; inorganic salts; pyridine, triethylamine and the like. Examples thereof include amines.

After the reaction, in order to isolate the desired compound of general formula (I), when a solvent soluble in water is used, the solvent is distilled off under reduced pressure, water is added, and then water is added. Insoluble in benzene, toluene, xylene and other aromatic hydrocarbons; chloroform, dichloromethane and other halogenated hydrocarbons; extracted with ethyl acetate and other esters and washed with saturated saline, and then anhydrous sodium sulfate, anhydrous magnesium sulfate, etc. It may be dried with the above desiccant and the solvent may be distilled off under reduced pressure. When a solvent insoluble in water is used, water is added to the reaction mixture and then liquid separation is performed,
The organic layer may be washed with saturated saline and then dried with a desiccant such as anhydrous sodium sulfate or anhydrous magnesium sulfate, and the solvent may be distilled off under reduced pressure. The residue obtained after evaporation of the solvent is purified by recrystallization, suspension washing, column chromatography or the like to obtain the target compound of the general formula (I).

The starting compound represented by the general formula (II) is
For example, it can be synthesized by the method described in JP-A-61-10560 and JP-A-61-10561. The compound represented by the general formula (III) as a raw material can be synthesized by the following method. (1) Reduction of phenylbenzonitriles

[0019]

[Chemical 5]

(In the above formula, R ³ , R ⁴ , m and n are as defined in the above general formula (I).) Phenylbenzonitriles (IV) and hydrogen are preferably added in the presence of a metal catalyst and aqueous ammonia. Use solvent, 0-100
The reaction is carried out at ℃, preferably 25 to 50 ℃. The solvent is not particularly limited as long as it does not directly participate in this reaction, and examples thereof include alcohols such as methanol, ethanol and isopropanol; aromatic hydrocarbons such as benzene, toluene and xylene; acetone, methyl ethyl ketone, methyl isobutyl ketone and the like. Ketones; halogenated hydrocarbons such as chloroform and dichloromethane; water; esters such as methyl acetate and ethyl acetate; or tetrahydrofuran, acetonitrile, dioxane, N, N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, pyridine And other polar solvents. Examples of the metal catalyst include Raney nickel, palladium carbon, platinum oxide and the like. After the reaction, in order to isolate the desired compound of the general formula (IIIa), the metal catalyst may be filtered off from the reaction mixture, and then the solvent may be distilled off under reduced pressure. It may be a pure product as it is, but if necessary, a pure product can be obtained by purification by means of distillation, column chromatography or the like.

Phenylbenzonitriles (IV) can be prepared by known methods, for example, synthetic communications, vol. 11, p. 513 (198).
By the method described in 1), it can be synthesized by reacting the corresponding haloarene and phenylboronic acid in the presence of a 0-valent palladium catalyst and a base. (2) Reduction of oximes

[0022]

[Chemical 6]

(In the above formula, R ² , R ³ , R ⁴ , m and n are as defined in the above general formula (I).) Oximes (V) and hydrogen in the presence of a metal catalyst and aqueous ammonia, Preferably using a solvent, 0 to 100 ° C, preferably 2
React at 5-50 ° C. The solvent is not particularly limited as long as it does not directly participate in this reaction, and examples thereof include alcohols such as methanol, ethanol and isopropanol;
Aromatic hydrocarbons such as benzene, toluene, xylene; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone; halogenated hydrocarbons such as chloroform, dichloromethane; water; esters such as methyl acetate, ethyl acetate; or tetrahydrofuran, Examples thereof include polar solvents such as acetonitrile, dioxane, N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide and pyridine. Examples of the metal catalyst include Raney nickel, palladium carbon, platinum oxide and the like. After the reaction, the general formula (I
To isolate the compound of IIb), the metal catalyst is filtered off from the reaction mixture, and then the solvent is distilled off under reduced pressure. Oximes
(V) can be synthesized by reacting the corresponding acetophenones with hydroxylamines in the presence of potassium carbonate by a known method.

The compound of the general formula (I) has the effect of controlling pests, mites and other pests, and is widely used in agriculture, forestry, animal husbandry, fisheries and the preservation of products in these industries and public health. In, it is effective for repelling pests, exterminating and controlling. Particularly, the compound of the present invention is used in agriculture, forestry, etc.
Specifically, at the time of growing agricultural products, pests that damage crops and trees, ornamental plants, etc., pest repellent in public health scenes, insecticides used for extermination and control, as acaricide, Shows excellent effects.

The following are specific usage scenes, target pests,
Although the usage method and the like are shown, the present invention is not limited to the following description. Further, the pests specifically exemplified are not limited to the target pests, and the pests exemplified also include adults, larvae, eggs and the like. (A) Agriculture, forestry scenes and the like; the compounds of the present invention are agricultural crops such as food crops (rice, wheat, corn, potato, sweet potato, beans, etc.), vegetables (brassicaceae crops, pickles, eggplant,
Tomatoes, leeks, etc., fruit trees (citrus fruits, apples, grapes,
Peaches, special crops (tobacco, tea, sugar beet, sugar cane,
Cotton, olives, etc.), grass and forage crops (sorghum, grasses, legumes, etc.) and ornamental plants (herbs, flowers, etc.)
It is effective for repelling and controlling pests such as arthropods, molluscs, nematodes, and various fungi that damage them in the case of raising garden trees). Furthermore, the compound of the present invention is a repellent of pests when storing harvested products from the above-mentioned crops such as grains, fruits, tree nuts, spices and tobacco, and products obtained by subjecting these to drying, pulverization and the like. It is also effective for extermination. It is also effective in protecting standing trees, fallen trees, processed wood, stored wood, etc. from damage by pests such as termites and beetles.

Specific pests include, for example, those belonging to the phylum Arthropoda, Mollusca and Nematoda,
The following can be mentioned. The following can be illustrated as an arthropod Insecta. The Lepidoptera include, for example, the family Moths such as Spodoptera litura, Helicoverpa armigera, Spodoptera litura, and Tamanaginu waaba;
Pleurotus spp., Such as Pleurotus spp. Orchidaceae such as mosquitoes; oriental mosquitoes such as peach mosquitoes; Lycaenidae, butterflies such as mugwort eddaks, spermaceae such as shrimp, etc .; killer whales such as monk orchids; It can gel.

Examples of the order Coleoptera include Scarabaeidae such as Scutellaria baicalensis, Spodoptera litura, and Scutellaria;
Buprestidae such as stag beetle, etc .; click beetle such as marcus beetle, etc .; ladybug family such as Nijuyahoushi tentou And the family Weevil beetle such as A. weevil and the family Weevil Weevil such as Weevil Weevil;

Examples of the hemiptera include stink bugs such as Chabaneata stink bugs and stink bugs; family stink bugs such as pest stink bugs; helicopteridae family such as horned stink bugs; helicopter stink bugs such as spider helicopter bugs; red stink bugs; Etc., such as Pleurotus stellidae; Gumbaiidae such as Nashigumbai; Mekakumeidae such as Usumiridimegurame; Cicada family such as Niizumii; Aphididae family such as grape brackish;
Family leafhoppers such as leafhopper leafhoppers, green leafhoppers and leafhoppers; leafhopper families such as leafhopper leafhoppers; planthoppers such as velvetleaf planthoppers and brown planthoppers; families of psyllidaceae such as psyllids; Phylloxaceae such as Aphis gossypii; Pseudococcidae such as apple beetle; Aphididae such as cotton aphid, green peach aphid, and red aphid, Aphididae such as Pteridophyta, and aphididae such as citrus scale insect, Rubiaceae; And the like, such as Pseudococcidae; and Pseudococcidae, such as Nashimarukaigara, Kurashirokaigara and the like.

Examples of the thrips include Thysanoptera such as Thrips palmi, Thrips palmi, Thrips palmi and the like, and Thrips thrips, such as Kykida thrips and Rice thrips. Examples of Hymenoptera include, for example, wasps such as bees, bees and wasps, such as apple wasps, and wasps, such as wasps, and hornets, such as rosehoppers. Examples of Diptera include soybean, Pyllidae and other gall midges;
Examples thereof include Drosophilidae such as rice fruit fly and the like; Drosophila family such as Drosophila melanogaster; Dactylidae such as Nagomi fly and Mamehaguribae; and Danaidae such as onion fly. Examples of Orthoptera include grasshoppers such as Wedges; crickets such as Aphididae; viperaceae such as viper; and grasshoppers such as cobainigo. Examples of Collembola include, for example, Malmobiidae, such as P. mellifera; and Aphididae, such as Pseudococcidae. Examples of the termites include, for example, termites such as Taiwanese termites, and examples of the earwigs include, for example, Coleoptera, such as Coccinellidae.

Examples of the arthropod crustacea and arachnid include the following. Examples of the isosceles of the crustacea include the pill bug family such as the pill bug. The mites of the arachnid class include, for example, dust mites such as Chano dust mites and cyclamen dust mites;
Examples of spider mites such as barley mites; families of mites such as grape mites; families of mites such as spider mites, kanzawa mites, citrus mites, apple mites; mites of mites rust mites, apple rust mites, mite mites, etc. it can.

Examples of molluscs as gastropods include gastropods of the class Gastropoda such as Spodoptera litura, and stalk eyes such as African snails, slugs, slugs, slugs, and mussels be able to. The following can be illustrated as a linear animal illusionary organ network and a tail line network. Examples of the genus Haricenchus include, for example, Anguinae such as Imogusaresenchuu; Tyrenkorinkusidae such as Namishukusenchuu; Platylenxaceae such as Kitaegusaaresenchu, Minaminegesaresenchu; Naprosmus nematodes; Examples thereof include heteroderidae such as nematodes; Meloidogyneceae such as sweet potato nematodes; Kuriconemae such as nematodes; Nototelenxaceae such as strawberry nematodes; and Aferencoides, such as strawberry nematodes. Examples of the genus Rhinoceros, Lepidoptera, include the family Longidoridae such as Pleurotus nematode; the family Trichodolaceae such as Yumihari nematode.

Further, the compound of the present invention is also effective for repelling, controlling and exterminating pests that damage trees or affect trees in natural forests, artificial forests and urban green areas. In such a situation, the following can be mentioned as specific pests. Examples of the arthropod phylum Insects and arachnids include the following. The Lepidoptera include, for example, Spodoptera vulgaris, Gypsy moth, etc .; Pleurotus spp., Such as Matsukareha, Tsugakareha; Kaigagae, such as Larix densiflora, etc .; Kagamiga, etc .; And the like, and the like, and the like, and the like.

The Coleoptera include, for example, Scarabaeidae such as Scutellaria japonicus and Scutellaria japonicus; Buprestidae such as Keyhole beetle; Cerambycidae such as Pseudococcidae; Chrysomelidae such as Scutellaria japonicus; Weevilidae; weevil family such as weevil; holly beetle family such as pine beetle, holly beetle, etc .;

Examples of the Hemiptera include aphids such as Aphis gossypii, Pseudomonas aphid such as Aedes albopictus, Pseudomonas aphid such as Pseudococcidae, and Pseudococcidae such as Aphididae. Examples of the Hymenoptera include, for example, the family Vespidae such as Larix mellifera, the family Vespidae such as pine wasp, and the family Vespidae such as Plutella. Examples of the diptera include Gangamidae such as Aedes albopictus; Dactylidae such as Larix melanogaster; Scutellariae including adults, larvae and eggs, and Pyllidae such as Matsusintometabei.

[0035] Examples of the mites of the arachnid class include, but are not limited to, Haemaphysalis longicornis, Todomatsunoha mites and the like. Examples of Helicoptera of the order Lepidoptera of the genus Nematoda include, for example, the family Parasitaferenx, such as pine wood nematode. The pest control agent containing the compound of the present invention as an active ingredient is an effective formulation in the above-mentioned agricultural or forestry scene, and any use form prepared by the formulation,
It can be used alone or in combination with other active compounds such as insecticides, acaricides, nematicides, fungicides, synergists, plant regulators, herbicides and poison baits, or as a mixture. The following are examples of more specific active compounds, but the present invention is not limited thereto.

Active compounds such as insecticides and acaricides: Examples of organic phosphorus agents include dichlorvos, fenitrothion, malathion, naredo, chlorpyrifos, diazinon, tetrachlorvinphos, fenthion, isoxathion,
Methidathion, salithion, acephate, zimeton-S
Methyl, disulfotone, monocrotophos, azinephosmesyl, parathion, phosalone, pirimiphos-methyl, prothiophos and the like can be mentioned. Examples of carbamate agents include methotrecarb, phenocarb, propoxur, carbaryl, ethiophencarb, pirimicarb, bendiocarb, carbosulfan, carbofuran, mesomil, thiodicarb and the like.
Examples of the organic chlorine agent include lindane, DDT, endosulfan, aldrin, chlordane and the like. Examples of the pyrethroid agent include permethrin,
Cypermethrin, deltamethrin, cyhalothrin, cyfluthrin, acrinathrin, fenvalerate, etofenprox, silafluofen, fluvalinate,
Examples thereof include flucitrinate, bifenthrin, allethrin, phenothrin, fenpropatorin, cifenotrin, flamethrin, resmethrin, transfluthrin, pralethrin, flufenprox, halofanprox, imiprothrin and the like. Examples of the neonicotinoid agent include imidacloprid, nitenpyram, acetamiprid, tefuranitodine, thiamethoxam, thiacloprid and the like.

Examples of insect growth regulators such as phenylbenzoylurea agents include diflubenzuron, chlorofluazuron, triflumuron, flufenoxuron, hexaflumuron, rufenuron, teflubenzuron, buprofezin, tebufenozide, chromafenozide, methoxyphenozide and cyromazine. be able to.

Examples of the juvenile hormone agents include pyriproxyfen, phenoxycarb, mesoprene, hydroprene and the like. Examples of insecticidal substances produced by microorganisms include abamectin, milbemectin, nikkomycin, emamectin benzoate,
Examples include ivermectin and spinosad.

Examples of other insecticides include cartap, bensultap, chlorfenapyr, diafenthiuron, nicotine sulfate, methaaldehyde, fipronil, pymetrozine, indoxacarb, tolfenpyrad and the like. As an active compound of acaricide, for example, dicofol, phenisobromolate, benzomate, tetradiphone, polynactin complex, amitraz, propargyl, fenbutatin oxide, tricyclohexyltin hydroxide, tebufenpyrad, pyridaben, fenpyroximate, pyrimidifen, fenazaquine,
Clofentedine, hexithiazox, acequinocyl,
Examples thereof include quinomethionate, phenothiocarb, etoxazole, bifenazate and the like.

Examples of the active compounds of nematicides include methylisocyanate, phostiazate, oxamyl and mesulfenphos. As poison bait,
For example, monofluoroacetic acid, warfarin, coumatetralyl, difacin and the like can be mentioned. Examples of the active compound of the fungicide include inorganic copper, organic copper, sulfur, manneb, thiuram, thiadiazine, captan, chlorothalonil, iprobenphos, thiophanatemethyl, benomyl, thiabendazole, iprodione, procymidone, penciclone, metalaxyl, sandfan, baileton, triflumione. Examples thereof include sol, phenalimol, triphorine, dithianon, triazine, fluazinam, probenazole, dietofencarb, isoprothiolane, pyroquilon, iminoctadine acetate, eclomezole, dazomet, and kresoxime methyl.

Examples of active compounds such as herbicides include bialaphos, setoxydim, trifluralin, mefenacet and the like. Examples of the active compound of the plant regulator include indole butyric acid, ethefone, 4-CPA and the like. As the active compound of the repellent,
For example, carane-3,4-diol, N, N-diethyl-m-triamide (Deet), limonene, linalool, citronellal,
Mentone, hinokitiol, menthol, graniol, eucalyptol and the like can be mentioned.

Examples of the active compound of the synergist include bis.
-(2,3,3,3-Tetrachloropropyl) ether, N- (2-
Ethylhexyl) bisclo [2,1,1] hept-5-ene-2,3-
Examples include dicarboximide and α- [2- (2-butoxyethoxy) ethoxy] -4,5-methylenedioxy-2-propyltoluene. The pest control agent of the present invention may be used in any form. For example, a pesticidal auxiliary agent may be added to the compound of the general formula (1) to prepare, for example, a wettable powder, a wettable granule, a water solution, an emulsion,
It is used by formulating into a fluid, a flowable agent such as a suspension in water and an emulsion in water, a capsule, a powder, a granule and an aerosol. The content of the active ingredient compound such as the compound of the present invention in these formulations is arbitrary, but is usually selected from the range of 0.001 to 99.5% by weight in the total amount of the active ingredients, the formulation form,
It may be appropriately determined according to various conditions such as application method,
For example, about 0.01 to 90% by weight for wettable powders, wettable granules, water solutions, emulsions, solutions, flowables, capsules, etc.,
Preferably 1 to 50% by weight, powder or granules, etc., about 0.1 to 50% by weight, preferably 1 to 10% by weight, aerosol, etc., about 0.001 to 20% by weight, preferably 0.01 to 2% by weight It is preferred to make it to contain the ingredients.

The agrochemical auxiliary used is, for example, a carrier (diluent), a spreading agent, an emulsifier for the purpose of improving pest repellent effect, control effect, extermination effect, stabilization, and dispersibility. A wetting agent, a dispersant, a disintegrating agent and the like can be used. As the liquid carrier, water, toluene, aromatic hydrocarbons such as xylene, alcohols such as methanol, butanol and glycol, ketones such as acetone, amides such as dimethylformamide, sulfoxides such as dimethylsulfoxide, methylnaphthalene, Cyclohexane,
Examples thereof include animal and vegetable oils and fatty acids. Further, as a solid carrier, clay, kaolin, talc, diatomaceous earth, silica, calcium carbonate, montmorillonite, bentonite, feldspar, quartz, alumina, sawdust, nitrocellulose,
Starch, gum arabic, etc. can be used. Usual surfactants can be used as the emulsifier and dispersant, and examples thereof include anionic surfactants such as higher alcohol sodium sulfate, stearyl trimethyl ammonium chloride, polyoxyethylene alkylphenyl ether, and lauryl betaine, and cations. A systemic surfactant, a nonionic surfactant, a zwitterionic system surfactant, etc. can be used. Further, spreading agents such as polyoxyethylene nonyl phenyl ether and polyoxyethylene lauryl phenyl ether; wetting agents such as dialkyl sulfosuccinate; fixing agents such as carboxymethyl cellulose and polyvinyl alcohol; sodium lignin sulfonate, sodium lauryl sulfate, etc. Disintegrants of can be used.

For example, in the case of a wettable powder, a compound represented by the general formula (I) which is an active ingredient, a solid carrier, a surfactant and the like are mixed to produce a bulk powder, which is further used at the time of use. It can be applied after diluting with water to a predetermined concentration. In the case of an emulsion, a stock solution emulsion can be prepared by mixing a solvent, a surfactant and the like with the above-mentioned compound as an active ingredient, and the stock solution may be diluted with water to a predetermined concentration before use. it can. In the case of powder, the above-mentioned compound of the active ingredient, solid carrier and the like can be mixed and applied as it is. In the case of granule, the above-mentioned compound of active ingredient, solid carrier, surfactant and the like can be mixed to prepare. It can be produced by granulating and applied as it is. However, the method for producing each of the above-mentioned preparation forms is not limited to the above, and can be appropriately selected by those skilled in the art according to the type of active ingredient, the purpose of application and the like.

The method of use depends on the type and amount of pests generated,
Depending on the type of crops / trees, etc., cultivation form / growth state, etc., for example, for arthropods, gastropods, nematodes, etc., the place where damage is usually caused by these pests, Or, for the place where damage is expected to occur, generally 0.1 to 1000 g of active ingredient per 10 ares,
It is preferable to apply 1 to 100 g.

Specific application methods include, for example, the wettable powders, granular wettable powders, water-soluble solvents, emulsions, solutions, flowable agents such as water-suspending agents and water-emulsifying agents, capsules and the like. It may be diluted with water and sprayed on the crops, trees, etc. within a range of 10 to 1000 liters per 10 are depending on the type of crops, trees, etc., the cultivation form and growth state. Further, in the case of powders, granules, and aerosols, they may be applied to crops, trees, etc. within the range of the above-mentioned method of use in the form of their formulations.

When the target pest mainly harms crops, trees, etc. in soil, for example, wettable powder, granule wettable powder, water solvent, emulsion, liquid agent, water suspension agent / water emulsion. In general, dilute the flowable agents such as agents and capsules with water,
It may be applied in the range of 5 to 500 liters per 10 ares. At this time, the agent may be sprayed on the soil surface or irrigated into the soil so as to be even over the entire application area. When the formulation is in the form of powder or granules, the formulation may be spread as it is on the soil surface so as to be even over the entire application area. In addition, during spraying or irrigation, it may be applied only to the periphery of seeds, crops, trees, etc. that are desired to be protected from damage by pests, or it may be cultivated during or after spraying to mechanically disperse the active ingredient. Good.

Furthermore, a pest control agent containing the compound of the present invention as an active ingredient may be attached to the periphery of plant seeds by a known method. By such a treatment, after sowing of this seed, not only can damage from pests in the soil be prevented, but after growth, the foliage and flowers of the plant,
It is also possible to protect fruits and the like from damage by pests.

When the above-mentioned trees and fallen trees, processed wood, stored wood, etc. are protected from damage by termites, beetles, etc., for example, an oil agent is applied to surrounding soil such as trees and wood,
Examples of the method include spraying / injecting / irrigating / coating an emulsion, a wettable powder, and a sol, and spraying the drug in the form of use such as powder and granules. Even in such a situation, a pest control agent containing the compound of the present invention as an active ingredient is used alone or other active compounds such as insecticides, acaricides, nematicides, fungicides, repellents and synergists. Can be used in combination with or as a mixture.

The content of the active ingredient compound such as the compound of the present invention in these preparations is arbitrary, but it is usually 0.0001 to 95% by weight as the total amount of the active ingredients, and 0.005 for oils, powders and granules. It is preferably contained in an amount of from about 10 to 10% by weight, and from 0.01 to 50% by weight for emulsions, wettable powders and sol preparations. Specifically, for example, in the case of controlling and controlling termites, beetles and the like, 0.01 to 100 g of the amount of the active ingredient compound per 1 m ² may be sprayed on the soil or the wood surface.

(B) Livestock industry, fisheries scene, etc. A pest control agent containing the compound of the present invention as an active ingredient is used internally or externally for animals such as livestock and fisheries, and pets kept at home. Harmful to arthropods, nematodes, trematodes, tapeworms, protozoa, etc. that parasitize and cause direct harm such as feeding of the skin and blood sucking, and damage such as spread of diseases It is effective in repelling, exterminating and controlling organisms, and can also be used in the prevention and treatment of diseases related to these pests. The target animals include vertebrates, for example, warm-blooded vertebrates such as cattle, sheep, goats, horses and pigs, and farmed fish; further, poultry, dogs, cats, etc., mice, rats, hamsters, squirrels. And rodents; carnivorous eyes such as ferrets and pets such as fish and experimental animals.

Among the pests, the followings can be exemplified as the arthropod phyla Insects and arachnids. Examples of the diptera include, such as Yamatoab, Tsumetogebuyu, Redfly, etc .; Muscaeidae such as blowfly, housefly, sandfly, etc .; Muscaeidae, such as botfly, and so on; Fleas of the family; genus Flies of the genus Drosophila, such as Drosophila melanogaster; families of the fly flies such as Drosophila melanogaster, Drosophila melanogaster; mosquitoes such as Aedes aegypti, Aedes mosquito, Aedes albopictus; It can be illustrated.

[0053] Further, as for Heptoptera, for example, cat flea,
An example is a human flea family such as a dog flea. Examples of the pediculida include porcelain lice, porcelain lice and the like, pediculidae; horse lice and the like, pediculidae; cattle lice and the like; pediculidae; and chicken lice, etc. Examples of the mite order of the arthropod spider spider include, for example, Ixodidae such as Haemaphysalis longicornis, Haemaphysalis longicornis, Haemaphysalis longicornis, Haemaphysalis longicornis, etc .;
Examples of the species include vulgare families such as raccoon spiders; genus Acaridae such as scabbard mites; genus Adenidae such as caterpillar mites and aerial mites;

The following can be given as examples of the linear zona bizoa. Examples of the roundworm include bovine hookworm, porcine nematode, porcine lungworm, ciliary nematode, tuberculosis tuberculosis, and the like. Examples of Ascariasis include Ascaris suum, Ascaris suum, and the like. As a flatmoth fluke,
Examples thereof include Schistosoma japonicum, liver tetsu, deer fluke, paragonimus westermani, and chick fluke of Japanese egg. Examples of tapeworms include leaf tapeworms, extended tapeworms, tapeworms of Beneden, tapeworms, tapeworms, and tapeworms with rings. In the class Protozoa Hymenorrhea,
For example, Histomonas is used as the protoflagellate order such as Le
ishmania, Trypanosoma, etc., as a polydipteran order, for example, Giardia, etc., and as a Trichomonas order, for example, Tri
Examples include chomonas.

Further, examples of Amoeba of the genus Carnivora include Entamoeba and the like, subclasses of Pyroplasma of the genus Sporozoa include Theilaria, Babesia and the like, and subclasses of the late sporozoa include, for example, Eimeria, Plasmodium and Toxoplasma. Etc. can be mentioned. The pest control agent containing the compound of the present invention as an active ingredient is a formulation effective in the above-mentioned livestock industry, fisheries scene, etc., and in any use form prepared by the formulation, alone or another active compound such as an insecticide. , Acaricide, nematicide, fungicide, synergist, plant regulator, herbicide, poison bait and the like, or can be used as a mixture. As a more specific active compound, "(A) agriculture,
The substances and the like exemplified in the section “Forestry scenes and the like” can be mentioned, but the substances are not limited to these.

As a specific application method, for example, it is mixed with feed of livestock, pets, etc., and a suitable orally ingestible pharmaceutical composition such as tablets, pills containing a pharmaceutically acceptable carrier or coating substance. , Capsules, pastes, gels, beverages, medicated feeds, medicated drinking water, medicated feeds, large-release pills, and other sustained-release devices that are retained in the gastrointestinal tract, orally administered or sprayed , Powder, grease, cream, ointment, emulsion, lotion, spot-on, pour-on, shampoo and the like can be administered transdermally.

As a method for transdermal administration or topical administration, a device (for example, a collar, a medallion or an ear tag) attached to an animal so as to control arthropod locally or systemically can be used. Specific oral administration methods and transdermal administration methods when used as an anthelmintic agent for livestock, pets and the like are shown below, but in the present invention, these administration methods are not necessarily limited to the following description. When administered orally as a medicinal beverage formulation,
Usually, it may be dissolved in a suitable non-toxic solvent or water together with a suspending agent such as bentonite or a wetting agent or other excipient to prepare a suspension or dispersion, and an antifoaming agent may be added if necessary. May be included. In the beverage preparation, generally the amount of the active ingredient compound is 0.01 to 1.0% by weight, preferably 0.01 to 0.1.
Contains by weight%.

For oral administration in a dry solid unit dosage form, capsules, pills or tablets containing a predetermined amount of the active ingredient compound are usually used. These use forms are prepared by homogeneously mixing the active ingredient with suitable milled diluents, fillers, disintegrants and / or binders such as starch, lactose, talc, magnesium stearate, vegetable gums and the like. To be done. In such a unit-use formulation, the weight and content of the anthelmintic agent may be appropriately set depending on the type of host animal to be treated, the degree of infection, the type of parasite, and the body weight of the host.

In the case of administration by a feed, methods such as uniformly dispersing the active ingredient compound in the feed, using the drug as a top dressing or using it in the form of pellets, and the like can be mentioned. In order to achieve the antiparasitic effect, the active ingredient compound is usually added to the final feed in an amount of 0.0001 to 0.05% by weight, preferably 0.0005 to 0.01% by weight.
Contains.

When dissolved or dispersed in a liquid carrier excipient, it may be parenterally administered to animals by intragastric, intramuscular, intratracheal or subcutaneous injection. Since it is administered parenterally, the active ingredient compound is preferably mixed with a vegetable oil such as peanut oil or cottonseed oil. In such pharmaceutical formulation,
Generally, 0.05 to 50% by weight of active ingredient compound, preferably 0.1
~ 0.2 wt%. Further, the preparation mixed with a carrier such as dimethyl sulfoxide or a hydrocarbon solvent can be directly or locally administered to the outer surface of livestock or pets by spraying or direct injection.

(C) Public Health Scenes, etc. The pest control agent of the present invention has a negative effect on clothing, food and the living environment, and also harms the human body, and carries and carries pathogens to the public. It is also effective in repelling, exterminating and controlling pests in hygiene situations, etc. for maintaining public health. Specifically, the pest control agent of the present invention includes, for example, wood inside and outside the house itself, processed wood products such as wooden furniture, stored food, clothing, books, animal products (skin,
Hair, wool, feathers, etc.) and plant products (clothes, paper, etc.), etc., which adversely affects hygienic life, Lepidoptera,
It is effective for repelling, exterminating and controlling beetles, spots, cockroaches, flies and mites. Specific examples of pests in such public health scenes include the following.

The following can be exemplified as the arthropods of the class Insecta. Examples of Lepidoptera include, butteridae, such as Monsiodora vulgaris; mosquito family such as Kunugikarehaga; family mosquito family such as Aoi iraga; family mosquito family such as Takeno Hosokuroba; family mosquito family such as Aedes aegypti, Aedes aegypti The genus Asteraceae; and the genus Asteraceae such as squid and koga. The Coleoptera include, for example, the family Scutellaria japonica, such as Red-eared beetle; the family Beetle family, such as bean-hammyo;
Weevil beetles such as weevils and weevils; Weevil beetle such as adzuki bean weevils, pea weevil, and bean weevils; Family beetle such as stag beetle; Family; Pleurotus cornucopidae such as scabbard beetle, beetle beetle, beetle beetle, etc .; Leopard beetle family such as fake beetle beetle;
It can be mentioned, for example, the stag beetle family such as C. chinensis, stag beetle, etc .;

Examples of Hymenoptera include Vespidae such as Vespidae; Ants such as Giant Beetle; and Vespidae such as Kyobibekko.
Examples of diptera include mosquitoes such as Yamatoyabuka; Nukaka such as Nukaka; Chironomid such as Sesuji chironomid; Musciidae such as Ashimadarabyu; Muscaeidae such as blueflies; Housefly such as housefly; Drosophilidae such as; Drosophilidae such as Sentinic fly; Drosophilidae such as Drosophila melanogaster;
Cheese flies such as cheese flies can be mentioned. Examples of the order Heptoptera include, for example, the human flea family such as the human flea. Examples of Mucocilia include, for example, the family Aphididae, such as the purple velvet bug. Examples of cockroaches include the German cockroach,
The German cockroaches and other cockroaches; the American cockroaches, the black cockroaches, the Yamato cockroaches and the like can be mentioned. Examples of the Orthoptera include, for example, the family Corogidae, such as the spotted horsetail horse, the horsetail horse. Examples of the pediculida include, but are not limited to, human lice such as head lice; pediculaceae such as lice. Examples of the Hemiptera include bed bugs such as bed bugs; and triatominidae such as giant turtles. The termites include, for example, Rhinotermitidae, such as Yamato termite, and Termite; Ravi termites, such as Daikoku termite, and the Anopheles, for example, Kochatate, such as Tsuyakochatete; and Konatatate, such as Hiratachate. it can. As the stains, for example, spots such as Yamato-spots and blemishes can be mentioned.

Examples of arthropod spiders include the following. Examples of mites include Ixodidae such as Schultze mites; Ternidae such as house dust mites; Chitomidae such as nymphalid mites; Plutella mites such as lice mites; Demodex mites such as Demodex mites; Chili mites such as Physcomitidae;
Examples thereof include the family Acarinae such as red chigger; the family Acaridae such as Phytophthoridae and mite, and the family Acaridae such as sugar mite. In addition, examples of the true arachnids include, but are not limited to, butterbur spiders, such as Pleurotus spp., Such as Pleurotus spp .; Acrid spiders, such as Ashida spiders; You can As a scorpion eye,
For example, the scorpion family such as scorpion can be mentioned.

Other examples of the arthropod phyla include, as examples of the Lepidoptera, formicoptera, for example, Tobismukade, Aoismcade, and the like. Further, examples of the arthropod Pylopoda, Ophiridaceae, include the millipede family such as Toyota millipede, and examples of the arthropod Crustacea include the family Vorticula family. Furthermore, examples of the annelid Lepidoptera, Chrysomelidae, include the Yamaviridae such as Yamabir.

The pest control agent of the present invention can be used alone or with other active compounds such as insecticides, acaricides and killers in the above-mentioned preparations effective in public health and in any use form prepared by the preparations. It can be used in combination with nematodes, fungicides, synergists, plant regulators, herbicides, poison baits and the like or as a mixture. Specific other active compounds include:
The substances and the like exemplified in the section “(A) Agriculture and forestry scenes” can be mentioned, but the substances are not necessarily limited to these.

The pest control agent of the present invention may be used in any form. For example, when protecting the above-mentioned animal products, plant products, etc., sprays such as oils, emulsions, wettable powders, powders, etc. And the like, treatment of smoking agents and fumes, installation of granules, tablets and poison baits, and spraying of aerosols. The amount of the active ingredient compound in these preparations is preferably 0.0001 to 95% by weight.

As a method of application, for pests such as arthropods that directly cause harm and arthropods that are vectors of diseases, for example, oils, emulsions, and Spraying / injecting / irrigating / applying wettable powders, spraying powders, fumigants, mosquito coils, self-burning fumes, heated fumes such as chemical reaction fumes, fumigants such as fogging,
Examples thereof include a method of treating with a formulation such as ULV agent. In addition, other formulation forms such as granules, tablets or poison baits can be installed, or floating powders, granules, etc. can be applied by dropping into waterways, wells, reservoirs, water tanks and other running or stopping water. Good.

Furthermore, for the damselfish, which is also a pest in agriculture and forestry, "(A) Agriculture, forestry scene, etc."
It is possible to control by a method similar to the method described in the section 1), and for flies and the like, a method of mixing in the feed of livestock so that the active ingredient is mixed in feces, and mosquitoes For such cases, it is also effective to use an electric mosquito trap to volatilize into the air.

The formulations of these use forms are present as a mixture with other active compounds as described above, such as insecticides, acaricides, nematicides, fungicides, repellents or synergists. The total amount of the active ingredient compounds contained in these preparations is preferably 0.0001 to 95% by weight. It is also possible to use it in combination with other active compounds at the time of use.

When protecting houses, wooden furniture, etc. from damage by termites, beetles, etc., for example, spraying, pouring, irrigating, and applying oils, emulsions, wettable powders, and sols to these and their surroundings. , Powders, granules and the like may be used to spray the drug. Even in such a situation, the compound of the present invention alone or other active compound,
For example, it can be used in combination with an insecticide, an acaricide, a nematicide, a bactericide, a repellent, a synergist, or the like or as a mixture.

The content of the active ingredient compound such as the compound of the present invention in these preparations is arbitrary, but it is usually 0.0001 to 95% by weight as the total amount of the active ingredients, and 0.005 for oils, powders and granules. It is preferably contained in an amount of from about 10 to 10% by weight, and from 0.01 to 50% by weight for emulsions, wettable powders and sol preparations. Specifically, for example, in the case of controlling and controlling termites, beetles, etc., 0.01 to 100 g of the amount of the active ingredient compound per 1 m ² may be scattered around or directly on the surface.

When repelling, exterminating and controlling pests such as causing harm to the human body and carrying or transmitting pathogens,
In addition to those mentioned above, suitable orally ingestible pharmaceutical compositions, etc., such as tablets, pills, capsules, pastes, gels, beverages, medicated feeds, medicinal products containing pharmaceutically acceptable carriers and coating substances Oral administration as drinking water, medicated feed, sustained-release large pills, other sustained-release devices designed to be retained in the gastrointestinal tract, or spray, powder,
It can be transdermally administered as grease, cream, ointment, emulsion, lotion, spot-on, pour-on, shampoo and the like. For specific formulation, refer to "(B) Livestock industry,
The prescription can be performed in the same manner as the method described in the section “Fisheries scene etc.”.

[0074]

EXAMPLES The present invention will be described in more detail with reference to Examples, Formulation Examples and Test Examples, but the present invention is not limited to these examples as long as the gist thereof is not exceeded. Example 1 Synthesis of 2- (tert-butyl) -4-chloro-5- [4- (4-trifluoromethoxyphenyl) benzylamino] -3 (2H) -pyridazinone 2- (tert-butyl) -4, 5-dichloro-3 (2H) -pyridazinone
A mixture of (0.75 g), 4- (4-trifluoromethoxyphenyl) benzylamine (0.95 g), potassium carbonate (0.49 g) and N, N-dimethylformamide (10 ml) was heated at 150 ° C for 2 hours. The reaction mixture was poured into water (50 ml) and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 0.55 g of compound NO.21 shown in Table-1. The melting point was 116-117 ° C.

Example 2 According to the method of Example 1, the compounds shown in Table-1 were synthesized.

[0076]

[Table 1]

[0077]

[Table 2]

[0078]

[Table 3]

[0079]

[Table 4]

[0080]

[Table 5]

The following are formulation examples of agricultural and horticultural insecticides and acaricides containing the compound of the present invention as an active ingredient, but the use form of the present invention is not limited to the following. Formulation Example 1: Wettable powder 20 parts by weight of the compound of the present invention, Carplex # 80 (white carbon, Shionogi Pharmaceutical Co., Ltd., trade name) 20 parts by weight, ST Kaolin clay (kaolinite, Tsuchiya Kaolin Co., trade name) 52 parts by weight, Solpol 9047K (anionic surfactant, Toho Chemical Co., Ltd., trade name) 5 parts by weight, Lunox P65L (anionic surfactant, Toho Kagaku Co., Ltd., trade name) 3 parts by weight are blended and uniformly mixed. And pulverized to obtain a wettable powder containing 20% by weight of the active ingredient.

Formulation Example 2: Dust 2 parts by weight of the compound of the present invention, clay (manufactured by Nippon Talc) 9
3 parts by weight, Carplex # 80 (white carbon,
Shionogi Seiyaku Co., Ltd., 5 parts by weight) were uniformly mixed and pulverized to produce a powder formulation containing 2% by weight of the active ingredient. Formulation Example 3: Emulsion 20 parts by weight of the compound of the present invention is dissolved in a mixed solvent consisting of 35 parts by weight of xylene and 30 parts by weight of dimethylformamide, and Solpol 3005X (a mixture of a nonionic surfactant and an anionic surfactant is added thereto. , Toho Chemical Co., Ltd., product name) 15 parts by weight, 20% by weight of active ingredient
An emulsion of was obtained.

Formulation Example 4: Flowable Agent 30 parts by weight of the compound of the present invention and Solpol 9047K 5
Parts by weight, sorbon T-20 (nonionic surfactant, Toho Chemical Co., Ltd., trade name) 3 parts by weight, 8 parts by weight of ethylene glycol and 44 parts by weight of water are wet-milled with Dynomill (manufactured by Shinmaru Enterprises Co., Ltd.). Then, 10 parts by weight of a 1% by weight xanthan gum (natural polymer) aqueous solution was added to this slurry mixture, and the mixture was thoroughly mixed and ground to prepare an active ingredient 20.
A weight percent flowable agent was obtained.

The following are test examples of agricultural and horticultural insecticides and acaricides containing the compound of the present invention as an active ingredient, but the use form of the present invention is not limited to the following. Test Example 1: Insecticidal effect on the larvae of Spodoptera litura, a cabbage cut leaf (diameter 6 cm) was immersed for 1 minute in a water diluted solution of the insecticide (wettable powder) of the present invention produced according to the formulation of Preparation Example 1. After soaking, air dry and place in a plastic cup (inner diameter 7 cm).
Five dead insects were released (1 concentration, 2 repetitions). The cells were kept in a thermostatic chamber at 25 ° C., and the life and death and agony of the larvae were examined 5 days after the release of the insects, and the insecticidal activity (%) was determined assuming that the agony insects were 1/2 dead. The results are shown in Table 2 (in the table below, the compound number corresponds to No. in Table 1).

[0085]

[Table 6]

Test Example 2: Acaricidal effect on adults of Nami-dani mite The stems of the green bean seedlings with one primary leaf left were inserted into a test tube containing water (capacity: 50 ml), and female adults of Nami-dani mite were applied per leaf. Inoculated 15 animals. One day after the inoculation, the leaves on which the spider mites were parasitic were soaked (for about 5 seconds) in a water diluted solution of the acaricide of the present invention (emulsion) produced according to the formulation of Formulation Example 3.
(1 concentration, 2 repeats). It was kept in a thermostatic chamber at 25 ° C., and the number of female adult mites on the leaves of the kidney bean was examined 5 days after the treatment, and the mortality rate (%) was determined based on the result. The results are shown in Table-3.
It was shown to.

[0087]

[Table 7]

[0088]

INDUSTRIAL APPLICABILITY The pyridazinones of the present invention have an excellent control effect against harmful insects and mites, and
It is an excellent insecticide and acaricide for epidemics. Furthermore, it is expected to be used as a pest control agent for various pests in terms of preservation of livestock, fisheries or various products, and public health.

   ─────────────────────────────────────────────────── ─── Continued front page    (72) Inventor Toshiki Fukuchi             1000 Kamoshida-cho, Aoba-ku, Yokohama-shi, Kanagawa             Within Mitsubishi Chemical Corporation F term (reference) 4H011 AC01 AC04 BA01 BB09 BB11                       BC01 BC06 BC18 BC19 BC20                       DA02 DA14 DA15 DA16 DC04                       DH03 DH14

Claims (9)

[Claims] 1. The following general formula (I): (In the formula, R ¹ represents a C _{1 to} C ₅ alkyl group, R ² represents a hydrogen atom or a C _{1 to} C ₃ alkyl group, and R ³ represents C _{1 to} C ^3.
₅ alkyl groups, C _{1 to} C ₅ haloalkyl groups, C _{1 to} C ₅
Is an alkoxy group, a C ₁ -C ₅ haloalkoxy group or a halogen atom. m shows the integer of 0-4. R ⁴ is C ₁
Alkyl group -C _8, haloalkyl groups C ₁ ~C _5, C ₁ ~
C ₅ alkoxy group, C _{1 to} C ₅ haloalkoxy group, C ₁
To C ₅ alkylthio group, C _{1 to} C ₅ alkylsulfinyl group, C _{1 to} C ₅ alkylsulfonyl group or halogen atom. n shows the integer of 0-5. X represents a halogen atom. ) Pyridazinones represented by. 2. The pyridazinones according to claim 1, wherein in the general formula (I), R ¹ is a tert-butyl group. 3. The pyridazinones according to claim 1, wherein in the general formula (I), R ² is a hydrogen atom. 4. The pyridazinones according to claim 1, wherein in the general formula (I), R ³ is a methyl group or a halogen atom. 5. The pyridazinones according to claim 1, wherein m = 0 in the general formula (I). 6. In the general formula (I), R ⁴ is C _{1 to} C ₅
And a C ₁ -C ₅ haloalkoxy group as defined in claim 1, wherein the pyridazinones are any of the above. 7. In the general formula (I), X is a chlorine atom,
The pyridazinones according to any one of claims 1 to 6, which is a bromine atom. 8. A pest control agent containing the pyridazinone according to claim 1 as an active ingredient. 9. An insecticide or acaricide containing the pyridazinones according to claim 1 as an active ingredient.