JPH06503825A - Heterocyclic pesticidal compounds - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

[Detailed description of the invention] , Mu This invention applies to arthropods, such as insects and mites, phlegmon, such as nematodes, and Novel pest control for pests such as molluscs, e.g. slugs Control these pests by contacting them with pesticides. It is about the method. This invention can also be used to control pests. or concerning new pest control agents and methods for producing such pest control agents. be.

European Patent Publication No. 294228 and European Patent Publication No. 294229, in particular, 03-C1, 5-substituted dithiane having a hydrocarbyl group or a substituted phenyl group is disclosed to have pesticidal activity. European Patent Publication No. 10 No. 2062 specifically describes 5-disubstituted amines having a hydrocarbon or heterocyclic group in the 2-position. It has been disclosed that minozitian has pesticidal activity.

A new class of 2.2.5-trisubstituted dithianes has been found to have pesticidal activity It was done.

Therefore, the present invention provides an effective amount of the following formula (I) as a pesticidal agent: [In the formula, Y is oxygen or a group S (0), m and n are 0.1 and 2, and 82M and R2'' may be the same or different (and cyano, nitro, methyl (optionally substituted with halogen), group 5 ( 0) qR' (where q is 0.1 or 2 and R7 is methyl or ethyl ) or group COR' (Here, R' is hydrogen, hydroxyl, 01-C4 alkoxy, 01-C4 alkoxy) (optionally substituted with fluoro) or the group NR"R" (where R9 and RIG are each selected from hydrogen, methyl or ethyl) ) selected from R4m, R4'', Rsa and R6b are each hydrogen, methyl, cyano or tri- R11M and R8b are selected from fluoromethyl, and Rsa is selected from C2 to C1. 1, secondary or tertiary alkyl group (optionally halogen, C1-C4 alkoxy or or optionally substituted with a C1-C4 cycloalkyl group), 01-C4 alkoxy or 03-C4 cycloalkyl group, and R″′ is hydrogen, hydroxyl, 0 1-C4 alkoxy, 01-C4 alkanoyloxy or 01-C4 alkyl ( optionally substituted with alkoxy), or R'' and Ro are ge m-dimethyl groups or combined together with the ring carbon to which they are attached 3- to 5-membered ring (optionally containing a heteroatom or olefin bond) and optionally an 01-C4 alkyl group (optionally substituted with halogen). (may be substituted)] pest control consisting of contacting with a compound having 8 to 30 carbon atoms of The present invention provides a method.

The term "halogen" means fluor, chloro, bromo or iodo.

The term "heteroatomic" refers to oxygen, sulfur (which may optionally be present in oxidized form) or nitrogen substituted with hydrogen or C1-C4 alkyl.

Preferably Y is oxygen or sulfur.

Preferably, R″″ and R2″ may be the same or different, and each selected from thyl, ethyl, cyanogen or trifluoromethyl.

Preferably Rxa is methyl.

Preferably 11(2b is methyl or cyano.

Preferably, R", R4b, R" and Rsb are each selected from hydrogen or methyl. and preferably they are all hydrogen.

Preferably, R'' is a second or is a tertiary alkyl group or a cyclopropyl group. Preferably Rh is t-butyl or 2.2.2-)-rifluor-1-methylethyl. ! I11 is hydrogen, methyl or ethyl, preferably R'' is hydrogen.

According to another embodiment of the present invention, in formula (I), Y, R", R", R4b, R ", R"I R"% R", m and n are as described above, and Rlb is cyano, nitro, group 5(0), R', group COR'' (where q, R? and and Ra are as above) or C3-C, alkyl group substituted with halogen. A compound is provided.

Compounds of formula (I) can exist in many stereoisomeric forms. The present invention It includes individual forms and stereoisomers as well as mixtures thereof. The present invention also provides Compounds of formula (I) containing radioactive isotopes, in particular tritium in which 1 to 3 hydrogen atoms or in which one or more carbon atoms are replaced with "C" include.

Preferred compounds among the compounds of the invention include: ・5(e)-t-butyl-2(e)-methyl-1,3-dithiane-2(a)-ka Rubonitrile ・5(e)-t-butyl-2(a)-methyl-1,3-dithiane-2(e)-ka Rubonitrile ・5(e)-t-butyl-2(e)-methyl-1,3-dithiane-2(a)-ka Rubonitrile-1(e)-oxide 5(e)-t-butyl-2(e)-methyl -1,3-dithiane-2(a)-carbonitrile-1,1-dioxide 2(e )-Methyl-5(e)-(1-methyl-2,2,2-trifluoroethyl)-1 ,3-dithiane-2(a)-carbo-5(e)-cyclopropyl-2(e)-mer Thyl-1,3-dithiane-2(a)-carbonitrile -5(e)-t-butyl-2(e)-methyl-1,3-year-old xathian-2(a) -Carbonitrile ・5(e)-t-butyl-2(e)-methyl-1,3-oxathian-2(a) -Carbonitrile-3(a)-oxide 5(e)-t-butyl-2(e)-methane Chil-1,3-year-old xathian-2(a)-carbonitrile-3(e)-oxide ・5(e)-t-butyl-2(e)-methyl-1,3-oxathian-2(a) -Carbonitrile-3,3-dioxide.

The present invention also provides a method for producing the compound of formula (1), which method are derived from methods well known in the art for the preparation of similar compounds. . That is, this compound can be produced by the following method (i), (ii) or (1ii). can be built.

Method (i) is the following formula (■): (In the formula, X is SH, Yl is SH or OH) with a suitable aldehyde or ketone or a reactive derivative thereof (this Here, the R-based substituents at the 2.4.5 and 6-positions are as described above), and then as necessary It consists of oxidizing one or two ring sulfur atoms, depending on the case.

This reaction is preferably carried out at non-crystal temperatures in the presence of a catalyst or dehydrating agent in a non-polar solvent. administered. Examples of suitable catalysts include dimethylformamide/dimethyl sulfate catalyst , and sulfonic acids or sulfonic acid group-containing perfluorinated resins or boron trifluoride - Lewis acids such as ester complexes, or stannic chloride or concentrated formic acid (which reacts Examples include catalysts such as (which also act as a medium). Examples of suitable solvents include , hydrocarbons such as benzene, toluene or xylene or dichloromethane. Examples include chlorinated hydrocarbons such as This reaction typically occurs at temperatures ranging from 0° to 200”. It has been successfully carried out at temperatures ranging from 20' to 120°C. Ru.

Suitable reactive derivatives of aldehydes and ketones include, for example, acetals and ketones. One example is tar.

Compounds of formula (n) can be prepared from the corresponding diols in which X and Yl are hydroxyl. can be done. Therefore, dithiols are derived from sulfonate derivatives (i.e. formula (If) Odors C4 alkyl or p-1yl) and hydroxythiol is a hydroxythiol in which X is a halogen, especially bromine, in formula (n). and Yl is a protected hydroxyl group, e.g. an acetoxy group. It can be manufactured via

This precursor is then treated with a suitable reagent to replace the halogen atom with a sulfur atom, For example, react with potassium thiocyanate or potassium thioacetate, then alkali Hydrolyze. The production of diols and their conversion to the corresponding dithiols is within the skill of the art. This can be carried out by a method well known in the art.

The aldehydes and ketones to be reacted with the compound of formula (n) are known in the literature or is prepared by methods described in the literature.

Method (ii) is a method in which one of Ram and R″″′ in formula (1) is cyano, and To produce a compound in which one of the two groups is an alkyl group that may be substituted with a halogen. If desired, the following reaction (a) or (b) will be used.

The reaction (a) is the following formula (■): is the reaction between the compound and the alkylating agent.

Examples of suitable alkylating agents include alkyl halides such as methyl iodide. can be lost. This reaction is carried out using an inert solvent, e.g. an ether such as tetrahydrofuran. at a non-cryogenic temperature, preferably in the range of -100 to 50'C, preferably in the range of -70 to 30'C. Suitably performed in the presence of a strong base such as butyllithium at temperatures in the range of °C be done.

Compounds of formula (III) contain aldehyde functional groups instead of nitrile groups. It is suitably produced by converting a reaction compound. This conversion results in aldehyde suitable O,N-bis(trifluoroacetyl)hydroxylamine. This can be carried out by reacting with a reagent. This aldehyde is 2- from unsubstituted dithiane or oxathiane, which is treated with a strong base such as butyllithium. by reacting with a formylating agent such as dimethylformamide in the presence of Manufactured by

The reaction (b) is the following formula (■): (In the formula, Rlm is C1-C4 alkyl, and R12 is substituted with halogen. methyl) is a reaction between a compound of and trialkylsilyl cyanide in the presence of an acid catalyst.

Preferably, the alkyl group in the trialkylsilyl cyanide reagent has 1 to 4 carbon atoms. and preferably a methyl group. Preferably, the acid catalyst is boron trifluoride ether. It is a Lewis acid such as a complex compound. This reaction is effective for halogenated hydrocarbons, e.g. in an inert solvent such as dichloromethane at non-crystal temperatures, e.g. in the range of -50 to 80°C. , preferably at a temperature in the range from 0 to 30°C.

The compound of formula (IV) is a compound of formula (II) and the following formula (wherein R" and R" are prepared by reacting with an appropriate orthoester of be able to. This reaction takes place in the presence of an acid catalyst such as p-+-luenesulfonic acid. It is successfully carried out at high temperatures, i.e. temperatures in the range of 50-180°C.

Method (1ii) is a compound of formula (I) in which one or more of m and n is other than 0. and such compounds are compatible with lower oxidation states. It can be produced by oxidizing a compound. This reaction is usually carried out in an inert solution. in a halogenated hydrocarbon such as acetonitrile or chloroform. , non-cryogenic, e.g. at a temperature in the range 0-100°C, preferably in the range 20-30°C. It will be carried out at Examples of suitable oxidizing agents include m-chloroperbenzoic acid, Examples include peracids.

This oxidation is successfully carried out in the presence of a buffer such as anhydrous sodium acetate. . A compound in which m is 2 and n is O is a compound in which m is 0 or 1 in formula (I). in a ketone, e.g. acetone, using potassium permanganate. , non-cryogenic, e.g. at a temperature in the range of -30°C to 100"C, preferably -10 to 30"C. It can be produced at temperatures in the range of °C.

Compounds of formula (1) are suitable for use in arthropods, such as insects and mites, breadcrumbs, such as nematodes. and molluscs, for example to control pests such as slugs. I can do it. Thus, the present invention provides an effective amount of a compound of formula (I) for use in arthropods, worms, etc. to animals and/or molluscs, or to environments where they are susceptible. Provided is a method for controlling arthropods, pharypids and/or molluscs. Also, books The invention comprises administering an effective amount of a compound of formula (I) to an arthropod, broadworm. and/or molluscs are animals (including humans) and/or plants (including trees) and (or) a method for controlling stagnation on stored products. Furthermore, the present invention In human and veterinary medicines to control arthropods, arthropods and/or molluscs. The present invention provides compounds of formula (1) for use in public health management as well as agriculture.

The term "control" means the amelioration of the current or future harmful effects of a pest. to kill adults, larvae and eggs, prevent reproduction, exterminate pests and (or) eradication, as well as any other influence on behavior.

The compounds of formula (I) can be used in fields, pastures, plantations, greenhouses, orchards and vineyard crops, It is particularly effective in protecting grasses, ornamental plants, and plantation and forest trees; Examples of these include grains (corn, wheat, rice, millet, oats, etc.). wheat, barley, sorghum), cotton, tobacco, vegetables and salad vegetables (legumes, oilseed) crops, cucumbers, lettuce, onions, tomatoes and peppers), field crops (e.g. potatoes) Potatoes, sugar beet, peanuts, soybeans, rapeseed), sugarcane, pasture crops and forage (e.g. alpha), farm crops (e.g. tea, coffee, cocoa, bananas) , oil palm, coconut, rubber, spices), orchard crops (e.g. stone fruits, citrus fruits) fruits, kiwifruit, avocados, mangoes, olives, walnuts), vineyard produce objects, ornamental plants, flowers and shrubs in greenhouses, gardens and parks, forests, farms and nurseries. Field trees (both deciduous and evergreen) and cultivated for industrial or pharmaceutical purposes There is protection for plants that are grown in Japan (for example, night grass).

In addition, the compound of formula (1) can be used in wood (growing, felled, processed wood). , in storage or for construction purposes) to wasps (e.g. Uroceras). erus) or beetles (e.g. 5 colytids, Brachys platypodid, lyctid, bostri bostrichid, cerambycid, It is also effective in protecting against attacks by anobiids.

Compounds of formula (I) may also be used in foods such as cereals, fruits, nuts, spices and tobacco. Stored products, whether intact, pulverized or formulated into a product, It is also useful in protecting against attack by moths, beetles and mites. Also, save Stored animal products, such as leather, hair, wool and feathers (in their original form or processed) (e.g. carpets or textiles) are also protected from attack by moths and beetles. and stored meat and fish are also protected from attack by beetles, mites and flies. Ru.

The compounds of formula (I) are useful for the control of public health pests such as cockroaches and ants. is also useful.

Compounds of general formula (I) may also be harmful to humans or livestock or may be prevalent as disease vectors. arthropods, arthropods or molluscs, such as those mentioned above; For pest control, especially tick, mite (a+fte), shira insects, chisels, midges, biting, noisy, fly-causing flies, mosquitoes, hemiptera It is also effective in controlling insects and snails.

The compounds of formula (I) can be used as such or diluted in known manner for the above-mentioned purposes. It can be used by applying it in the form of a dipping agent, spray, atomization, etc. agents, lacquers, foams, dusts, powders, aqueous suspensions, pastes, gels. creams, shampoos, greases, flammable solids, vaporized mats, Flammable coils, poison baits, supplementary foods, hydrating powders, granules, aerosols, emulsifying concentrates, oil-based Suspensions, oil solutions, pressurized fillings, impregnated products, microcapsules, bore-on formulations or other standard formulations well known to those skilled in the art. The spray can be applied manually or by means of spray lace or arches, or by means of a vehicle or aircraft. It can be applied depending on the location. Animals, soil, plants or other surfaces to be treated , the propellant may be applied in large quantities and saturated by this; may be applied in a very small amount to cover only the surface. Immersion concentrates themselves It is not applied in the immersion bath where the animal is diluted with water and contains the immersion cleaner. immersed in. Aqueous suspensions can be applied in the same manner as sprays or dips. Wear. Powders can also be applied by duster or, in the case of animals, in perforated bags. It can also be placed in a tree or attached to a scraping stick. Paste, shampoo Greases and greases can also be applied manually or with inert materials, e.g. When sprayed on the surface of a material where objects rub their bodies against the material and transfer this to the skin. You can also Bore-on formulations are those in which all or most of the liquid is retained on the animal. It is applied as a volume of liquid on the back of the animal so that it is absorbed.

The compound of formula (1) can be used as a formulation ready for use on animals, plants or surfaces. or can be manufactured as a formulation requiring dilution before use, but both types The formulation comprises a compound of formula (1) in intimate admixture with one or more carriers or diluents. Contain as a substance. The carrier may be liquid, solid or gaseous; , or a mixture of these substances (the compound of formula (I) may consist of 0.025-99% <w/v depending on whether further dilution is required ) can exist at a concentration of

Dusts, powders and granules and other solid formulations may contain compounds of formula (I). Powdered solid inert carriers, such as suitable clay, kaolin, bentonite, Attapulgite, adsorbent carbon black, talc, mica, silica, chalk, stone plaster, tricalcium phosphate, powdered cork, magnesium silicate, vegetable carrier, Contains as an intimate mixture with starch and diatoms. Such solid formulations are generally Then, a solid diluent is impregnated with a solution of the compound of formula (1) dissolved in a volatile solvent. , evaporate the solvent and grind the product to obtain a powder, if desired. It is manufactured by granulating, solidifying or encapsulating the product.

A propellant for a compound of formula (I) in an organic solvent, such as those listed below. solutions, or emulsifying concentrates (also called water-miscible oils) (this is for immersion purposes) Aqueous emulsions prepared on the farm (which can also be used for immersion cleaners) or a spray cleaning agent). Such concentrates contain active ingredients in organic solvents and and with or without one or more emulsifiers. solvent can be present in a wide range, but may be present in 0-99.5% (W/V) of the composition. Preferably, it is present in an amount. This solvent may be eg kerosene, ketone or alcohol. , xylene, aromatic naphtha, water, mineral oil, aromatic and aliphatic esters and compounding industry Other solvents known to those skilled in the art may be selected. The emulsifier concentration can be varied over a wide range. Although it can vary, it is preferably in the range of 5 to 25% (W/V). This emulsifier is Preferably, polyoxyalkylene esters of alkylphenols and hexylphenols are used. Nonionic surfactants containing anhydrous polyoxyethylene derivatives and lauri sodium sulfate, sulfate ethers of aliphatic alcohols, alkylaryl sulfonate Sodium and potassium salts of sulfosuccinic acids, sodium and potassium salts of alkyl sulfosuccinic acids Anionic surfactants including salts, soap, lecithin, hydrolyzed glue, etc. It is.

Wettable powders include an inert solid carrier, one or more surfactants, and optionally stabilizers. and/or contains an antioxidant.

Emulsifying concentrates contain emulsifiers and often organic solvents such as kerosene, ketones, Alcohol, xylene, aromatic naphtha and other solvents well known in the art. Contains agents.

Wettable powders and emulsifying concentrates usually contain from 5 to 99.5% by weight of active ingredient, and It is diluted, for example with water, before use.

Lacquering agents dissolve the active ingredient in an organic solvent together with a resin and optionally a plasticizer. The solution consists of

Immersion cleaners can not only be prepared from emulsifying concentrates but also have formula (I) Wettable powders, soaps made by intimately mixing a compound with a dispersant and one or more surfactants It can also be prepared from dipping liquids and aqueous suspensions.

Aqueous suspensions of a compound of formula (I) may be prepared in combination with suspending agents, stabilizers or other agents. It may be suspended in water. Suspensions or solutions may not be applied by themselves. It can also be applied in known manner in diluted form.

Greases (or ointments) include vegetable oils, synthetic fatty acid esters, wool fat and soft paste. It can be manufactured from an inert substrate such as ruffin. The compound of formula (I) is Preference is given to homogeneous dispersion by means of mixtures in the form of solutions or suspensions. Also, The ointment base can be made by diluting an emulsifiable concentrate with an ointment base.

Pastes and shampoos may also be prepared by applying the compound of formula (I) to a suitable substrate, e.g. Semi-solid that can exist homogeneously dispersed in soft or liquid paraffin formulation or a non-greasy base with glycerin, mucilage or suitable soap. It is made based on. Greases, shampoos and pastes are usually These are applied without dilution to the appropriate amount required for processing. of the compound of formula (I).

Aerosol sprays combine the active ingredient with an aerosol propellant as well as a co-solvent (e.g. rogenated alkanes, propane, butane, dimethyl ether and the above-mentioned solvents). It can be produced simply by dissolving it.

A bore-on formulation is one in which a compound of formula (I) is dissolved or suspended in a liquid medium. It can be manufactured as In addition, avian and free mammalian hosts may contain compounds of formula (I). By having a plastic article impregnated with and appropriately shaped, It can also protect against ectoparasitic mites. Such items may impregnated collars, tags, bands, sheets and and strips. Preferably the plastic material is polyvinyl chloride (PVC) It is.

The concentration of the compound of formula (I) to be applied to animals, houses, other materials or outdoor areas is depending on the compound selected, the time interval between treatments, the nature of the formulation and the presence or absence of infestation. Although it varies, generally 0.001 to 20.0% (w/v) of the compound should be present in the formulation to which the compound is applied, preferably from 0.01 to 10%. It is. The amount of compound deposited depends on the compound selected, the method of application, the area of application, and the size of the animal. the concentration of the compound in the applied formulation, the factors by which the formulation is diluted and the nature of the formulation. It varies depending on the situation.

Undiluted formulations, such as bore-on formulations, are typically 0.1-20.0% (w/w), preferably in a concentration in the range from 0.1 to 10%. for storage products The amount of compound to be applied generally ranges from 0.1 to 20 ppm. space space The spray is an average of 0.001 to 1 mg of compound of formula (I) per rrr of treatment space. It can be applied to give a uniform initial concentration.

Compounds of formula (I) are also useful for protecting and treating plant species. In this case is an effective amount of the active ingredient as an insecticide, acaricide, nematocide or molluscicide. used. The amount applied depends on the selected compound, type of formulation, mode of application, plant species, and planting density. This varies depending on the degree of infestation, presence or absence of infestation, and other similar factors, but generally The suitable usage amount for the product ranges from 0.001 to 3 kg/ha, preferably ranges from 0.01 to 1 kg/ha. A typical agricultural formulation is 0 ．． 0001% to 50% by weight of a compound of formula (I), preferably from 0.1% to 50% by weight. Contains 15% by weight of compound of formula (I).

Powders, greases, pastes and aerosol formulations are usually prepared as described above. applied in a random manner, the compound of formula (I) is o,ooi in the applied formulation. It can be used at a concentration of ~20% (w/v).

The compound of formula (I) is a compound of the common house fly (Musca domestica). estica)). Furthermore, of formula (I) Certain compounds have activity against other arthropods. These arthropods Examples include Myzus persicae, Tetra Tetranychus urticae, Plutella Xylostella (Plutella xylostella), Curex (Cu lex) species, Tribolium castanelum eum), Sitophilus granar ius), Periplaneta americana (Periplaneta ameri) cana) and Blattella germanica a) is mentioned. Compounds of formula (I) are therefore suitable for arthropods, such as insects and Environments where mites are pests, such as agriculture, animal husbandry, public health management, and domestic environments. It is useful for controlling these arthropods in plants.

Examples of insect pests include Coleoptera (e.g. Anobium, Ceuthorrhynchus, Rhynchophorus chophorus), Cosmopolites, Lysolo Butrus (Li5sorhoptrus), Meligethes ), Hypothenemus, 1ylesin us), Acalya+a+a, Le+*a, Sairio Psylliodes, Leptinotarsa ), Gonocephalum, Agriotes otes), Dermolepida, Heteronicus (Het. eronychus), Phaedon, Tripolium (Trib olium), Sitophilus, Diabrochi brotica), Anthono+ous or Anthrenus (Anthrenus species), Lepidoptera (e.g. Ephestia ), Mamestra, Nearias (p, arias), Pecti Nophora (Pectinophora), Ostrinia (Ostrinia), Trichoplusia, Pieris, Laphygo+a, Agrotis, Amade Amathes, Wiseana, Tryp orysa), Diatraea, Sporganotis ganthis), Cydia, Archips, Plutella (Plutel la), Chilo (Chilo), Heliosis (He1i) othis), Subodoptera (5podoptera) or Tineola (Tineola) ola species), Diptera (e.g. Musca, Aedes, Anopheles, Culex, Glossina ( Glossina), Simulium, Stomoxis (S tomoxys), Haematobia ()Iae+aatobia), Tabana- Tabanus, Hydrotaea, Lucilia ilLal, Chrysoma, Callitr oga), Dermatobfa, Gasterophilus (Ga 5terophi 1us), Hypoderma, Hiremiia (Hyle+myia), Atherigona, Chlorobus (Chlorops), Phytomyza, Ceratitis (C eratitis), Liriomyza and Mellophagus (M Phthiraptera (Elophagus species), Phthiraptera (Food) Trichoptera, such as Damalina species, as well as Cercoptera, such as Rhinog. Linognathus and Haematopinu s) species), Hemiptera (e.g. Aphis, Bemisia (13emis) a), Pholodon, Aeneolami a), Empoasca, Parkinschera siella), Pyrilla, Aonidie lla), occus (:occus), Pseudo occus coccus), Helopeltis, Lygu s), Dy5dercus, Oxycarenus nus), Nezara, Aleurodes , Triatoma, Rhodnius, Sa. Psilla, Myzus, Megoura , Phylloxera, Adelyes, Niloparvata, Nephrotheticus etix) or Cimex species), Orthoptera (e.g. Locusta) custa), Gryllus, Schistoc erca) or Acheta species), Hymenoptera (e.g. Platen (Bl) attella), Periplaneta or platter (B species), Hymenoptera (e.g. Athalia, Cephas (C ephus), App (Atta), Solenopsis or Monomorium species), Isoptera (e.g. Odontotel Odontotermes and Reticulit ermes species), Microptera (e.g. Ctenocephalides ides) or Pulex species); isma species), Hymenoptera (e.g. Forficula species) ), Chalyptera (e.g. Peripsocus species) and Hymenoptera ( Examples include Thrips tabaci.

Examples of mite pests include ticks, such as Boophilus ), Ornithodorus, Ribicephalus (Rh ipicephalus), Amblyomma genus, Hia Genus Hyalom+wa, Ixodes IiE, Hemafu Genus Haemaphysalis, Dermace genus Ntor, genus Anocentor, mites and Mite anges), such as Acarus, Tetranicus anychus, Psoroptes, Notodones ednes), Sarcoptes (5arcoptes), Sorergates (Pso regates), Chorioptes, Euthrombi Cura (EutrombLcuLa), Demodex (Demodex), Bano Panonychus, Bryobia and Elio Eriophyes species may be mentioned.

Directly attack plants and trees important in agriculture, forestry, and horticulture, or attack by spreading bacterial, viral, mycoplasma or fungal diseases; Examples of nematodes that attack root-knot nematodes [e.g. yne) species (e.g. Meloidogyne incognita ncognita))], cystic nematodes [e.g. Globodera ra) species (e.g. Globodera rostoensis tochiensis), Heterodera species (e.g. Heterodera avenae), Radfuo Radophulus species (e.g. Radopulus similis) holussimilis))], focal nematodes [e.g. Pratylenchus species (e.g. Pr atylenchus pratensis)), Belonorhymus (Be1 onolaiIIlus species (e.g. Belonolaimus gracilis) olaLmus gracilis)), Tylench ulus) species (e.g. Tylenchul us semipenetrans)), rotidine class (Rotylenc) hulus species (e.g. Rotylench ulus reniformis), Rotylenchus us) species (e.g. Rotylenchus rob ustus)), Helicotylenchus sp. (For example, Helicotylenchu s multicinctus), Hemicyclophora (He+5icycl iophora) species (e.g. Hemicyclyophora gracilis cliophora gracilis), Criconemoides moides) species (e.g. Criconemoides similis) des 51mlis)), Trichodorus species (e.g. For example, Trichodorus primiti (vus))], dagger nematodes [e.g. Xiphinema species (e.g. Xiphinema diversi caudatum), Longidorus species (e.g. Longidorus elongatus (Longidorus elongatus) , Hoplolaimus species (e.g. Hoplolaimus colo Nanasu (l (oplolaimus coronatus)) *Anoelenko Aphelenchoides species (e.g. Aphelenchoides lysae) Aphelenchoides ritzema-bosi, anno Aphelenchoides besseyi )], stem bulb nematodes [e.g. Ditylenchus species (e.g. DLtylenchus dLpsaci)] is mentioned. can be lost.

Direct attacks on plants and trees important for agriculture, forestry and horticulture, or Attack by spreading bacterial, viral, mycoplasma or fungal diseases Pests of molluscs such as Naskuji, such as Derocera s) species (e.g. Deroceras retLc ulatut*) (gray field Naskuji), Arion group l, Mila Milax species, land snails such as Helix species and water 0 people including live snails, such as Planorbis species Examples of molluscan pests that are vectors of diseases of animals and livestock include Bulinus linus) sp., Physops Ls sp., Branorbis (Pl Anorbis spp. and Oricomelania spp. It will be done.

The compounds of the present invention may also include one or more other pesticidal active ingredients ( e.g. pyrethroids, carbamates, lipid amides and organophosphates) and Can be used in combination with insecticides (or) attractants, repellents, bactericides, fungicides, anthelmintics, etc. Ru. Additionally, the activity of the compounds of the invention may be affected by synergists or potency enhancers, such as piperoni oxidants such as rubtoxide or propyl 2-propynylphenylphosphonate. Synergists of the sidase inhibitor system, second compounds within the scope of the invention or pyrethroids This can be enhanced by the addition of a pesticide-based pesticide. oxidizer When an enzyme inhibitor system synergist is present in the formulations of the invention, the synergistic partner is a compound of formula (I). The ratio of the substances is in the range of 500:1 to 1:25, for example approximately 100:1 to 1O:1 Will.

As a stabilizer to prevent possible chemical decomposition of the compounds of the invention, , for example, antioxidants such as tocopherols, butylated hydroxyanisole and butylated hydroxytoluene), scavengers (e.g. epichlorohydrin) and organic or inorganic bases (e.g., which can act as basic stabilizers and scavengers). trialkylamines such as triethylamine).

The following examples are intended to illustrate the preparation and properties of compounds of the invention.

example".

5　e　-t-butyl-2e　-methyl-1,3-dithiane-2a　-carbony dwell (i) 5-t-butyl-1,3-dithiane (EL Eliel (E, L, E Liel et al., Journal of the American Chemical Society 4-(J Our own of the American Chemical 5ocie tylJ, Vol. 98 (1976), No. 12, p. 3583) 5g in tetra A stirred solution in 50 mA of hydrofuran was heated to -30°C under a nitrogen atmosphere. , 17.75 mff of a 1.6 M n-butyllithium solution in hexane was added. Added. After stirring for an additional hour, the mixture was added to the raw solution cooled to −10°C. It was added dropwise by syringe into 10 mβ of dimethylformamide.

The mixture was stirred at -10°C for 1 hour and then stored at 0°C overnight. . The reaction mixture was then poured into ice water 100rr+j2 and extracted with hexane. . The aqueous layer was neutralized with dilute hydrochloric acid and then extracted again with diethyl ether.

The ether extract was dried over anhydrous magnesium sulfate and evaporated under vacuum to give a white 3.1 g of solid residue was obtained. The thus obtained 5-t-butyl-2-formyl- 1,3-dithiane existed mostly as a dimer.

(if) 5-t-butyl-2-formyl-1,3-dithiane Ig under nitrogen atmosphere was heated to melt and then cooled. The viscous oil thus obtained was mixed with pyridine. The mixture was taken out into 100 mβ of dry benzene containing 0.78 g of carbon.

0, N-bis(trifluoroacetyl)hydroxylamine (J-H-vomero In(J,)1. Pomeroy et al., “Journal on American ・Chemical Society” Vol. 81 (1959), p. 6340) 1.1g was added and the resulting mixture was heated under reflux for 2 hours. After cooling, ether and Water was added and the organic layer was separated. The aqueous layer was further extracted with fresh ether, and the organic The combined effluents were dried over anhydrous magnesium sulfate and then evaporated under vacuum. , a yellow solid was obtained, which was purified by column chromatography on silica. Purified. 5- 0.38 g of t-butyl-2-cyano-1,3-dithiane was obtained as a white solid. It was.

(1ii) 0.2g of 5t-butyl-2-cyano-1,3-dithiane in tetra A solution contained in 10 mβ of hydrofuran was cooled to -40°C under a nitrogen atmosphere. Ta. Add 0.7 mA of 1.6M n-butyllithium solution in hexane to obtain The resulting mixture was heated to -40°C for 1.2 ml with the addition of 0.2 ml of methyl iodide. It was held for 5 hours. The reaction mixture was allowed to warm to room temperature and left overnight. Next is Diechi ether and water were added. Separate the organic layer and extract the aqueous layer with fresh ether. Ta. The combined organic extracts were dried over anhydrous magnesium sulfate and evaporated under vacuum. I set it. The residue was subjected to column chromatography using alumina (eluent: hexane and after recrystallization from hexane) and recrystallization from hexane. , 5(e)-t-butyl-2(e)-methyl-1,3-dithiane-2(a)-ka 100 mg of rubonitrile was obtained as a white solid.

Ninety-one 5e-t-butyl-2a-methyl-1,3-dithiane-2e-carbonite lil (i) 2-t-butylpropane-1,3-dithiol (European Patent Publication No. 2) 94228) and 1.5 m of acetaldehyde in dry chloroform. Boron trifluoride ether complex compound is added to the stirred solution in a nitrogen atmosphere under a nitrogen atmosphere. 2.15 rr+J2 was added. The resulting mixture was stirred at room temperature overnight. . The mixture was then washed with water, saturated sodium bicarbonate solution and brine, then was dried over anhydrous magnesium sulfate and evaporated under vacuum. 5-t-butyl-2 4.7 g of methyl-1,3-dithiane were obtained as a pale yellow oil, which was cooled. It solidified when it was cooled.

(if) Using the method described in steps (i) and (if) of Example 1, 5-t-butyl 5(eit-butyl-2(a)-methyl- Converted to 1,3-dithiane-2(e)-carbonitrile.

Takumi Yu 5e-t-Butyl-2,2-dimethyl-1,3-dithiane Example 2 Step (i) acetone and 2-t-butylpropane-1,3-dithi using the method described in Production of 5(e)-t-butyl-2,2-dimethyl-1,3-dithiane from alcohol did. The crude product was chromatographed on silica (eluent: hexane and dichloromethane). 9:1 mixture with lormethane) followed by chloroform/methanol. Purified by recrystallization.

i, i, i -trifluoroacetone and 2-t-butylpropane-1,3 - In a similar manner starting from dithiol, cis-/trans-5(e) -Produce t-butyl-2-methyl-2-trifluoromethyl-1,3-dithiane did.

Takumi A 2　e　-Methyl-5e　-2,2,2-)-lifluoro-1-methylethyl- 1,3-dithiane-2a-carbonide (i) boron trifluoride ether compound 2.9 To a refluxing solution containing mQ and 10 mA of glacial acetic acid in 50 mβ of chloroform , 2-(2,2,2-trifluoro-1-methylethyl)propylene under nitrogen atmosphere. Pan-1,3-dithiol (European Patent Publication No. 0372816A) 4.8 g and 2.1 mβ of dimethoxymethane in 15 mβ of dry chloroform. The mixture was added. This addition was carried out over a period of 1 hour and the resulting mixture was It was refluxed for an additional 2 hours and then stirred at room temperature overnight. The reaction mixture was then diluted with water. , washed with saturated sodium bicarbonate solution and brine, then with anhydrous magnesium sulfate. Dry and evaporate under vacuum. The thus obtained 5i2.2.2-trifluoro 3.6 g of (1-methylethyl)-1,3-dithiane without further purification ( Using.

(ii) Using the method described in Example 1, 5-(2,2,2-trifluoro-1- methylethyl)-1,3-dithiane to 2(e)-methyl-5(e)-(2,2, 2-trifluoro-1-methylethyl)-1,3-dithiane-2(a)-carbo Converted to nitrile.

2-(1,1-dimethyl-2,2,2-)lifluoroethyl)propane-1,3 - similar starting from dithiols (European Patent Publication No. 0372816A) In the method, 5(el-(1,1-dimethyl-2,2,2-trifluoroethyl)- 2(e)-Methyl-1,3-dithiane-2(a)-carbonitrile was produced.

2-Cyclopropylpropane-1°3-dithiol (European Patent Publication No. 03) 72816A) in a similar manner starting from 5(e)-cyclopropyl-2( e)-Methyl-1,3-dithiane-2(a)-carbonitrile was produced.

Takumiji 5e-t-butyl-2e-methyl-1,3-year-old xathian-2a-cal Bonitrile (i) 2-tert-butylpropane-1,3-diol (E. L. Eliel et al. Journal on American Chemical Society, Volume 90 (1968 ), p. 3444) in 200 mj2 of dry toluene. The mixture was stirred at 20°C. 80% sodium hydride suspension in oil 2.4 g (washed with xane) were carefully added to the stirred mixture. this The mixture was stirred at 120° C. for 30 minutes and cooled. Benzyl bromide 9.5m℃ was added dropwise and the mixture was heated to 130° C. for 6 hours with stirring. this mixture Cooled, water was added and the mixture was extracted with diethyl ether. ether extraction The liquid was washed with water, dried over anhydrous magnesium sulphate and evaporated under vacuum. residue chromatography on silica (eluent: diethyl ether and hexane) (1:4 mixture).

2-benzyloxymethyl-3,3-dimethylbutan-1-ol8. No Og Obtained as a colored oil.

(ii) 2-benzyloxymethyl-3,3-dimethylbutan-1-ol 5 , 8 g were stirred in 20 mβ of dry pyridine at 0°C, followed by methane chloride. 3.5 g of Rufonyl was added dropwise and the mixture was incubated at 0°C for 3 hours and at 20°C. The mixture was stirred for 5 hours. Water was added and the aqueous mixture was extracted with diethyl ether. workman The ether extract was washed with water, dried over anhydrous magnesium sulfate, and evaporated under vacuum. I set it.

2-benzyloxymethyl-3,3-dimethyl-1-butyl methanesulfonate 7 ．． 3 g were obtained as a yellow oil, which was used without further purification.

(1ii) Benzyl mercaptan 3.1 m℃ dried dimethylformamide 10 Stirred at 0°C under nitrogen flow in 0tnj2. 80% hydrogenated sodium in oil Carefully add 0.75 g of the powder suspension (previously washed with hexane) and The mixture was stirred at 0°C for 30 minutes. 2-benzyloxime methanesulfonic acid 7.3 g of methyl-3,3-dimethyl-1-butyl was added to 20 g of dry dimethylformamide. +nJZ and the resulting mixture was heated at 100°C for 3 Stir for hours. The mixture was cooled and water was added. Add the aqueous mixture to diethyl ether Extracted with tel. The ether extract was washed with water and dried over anhydrous magnesium sulfate. and evaporated under vacuum. The residue was chromatographed on silica (the eluent was A mixture of diethyl ether and hexane in a ratio of 1:4) was used. 2-be 7.0g of dimethylthiomethyl-3,3-dimethylbutylbenzyl ether is a colorless Obtained as an oil.

(iv) 400 mβ of anhydrous liquid ammonia was stirred at -70°C under a nitrogen flow. . 2-benzylthiomethyl-3,3-dimethylbutylbenzyl ether 7.0g was added in 100 mε of dry diethyl ether, and then 4.0 g of small pieces of lium were added. The resulting mixture was stirred at -70°C for 3 hours. and then warmed to 20°C. Add 20 g of ammonium chloride and then dry 70 mff of tanol was added. When all the sodium has dissolved, add water and This mixture was extracted with diethyl ether. Wash the ether extract with water and make it anhydrous. Dry with magnesium sulphate and evaporate under vacuum. 3.3-dimethyl-2-meth 2.8 g of lucatomethylbutan-1-ol were obtained as a pale yellow oil; This was used without further purification.

(v) 1.66 g of 3,3-dimethyl-2-mercaptomethylbutan-1-ol , 1.82 g of triethyl orthoacetate and p-)luenesulfonic acid (catalytic amount). The mixture was heated under a stream of nitrogen until no more ethanol evolved. The resulting brown The oil was chromatographed on alumina (eluent was 4% dichloromethane in hexane). Purified by lormethane (saturated with ammonia). 5-t-buty 1.0 g of Ru-2(a)-ethoxy-2(e)-methyl-1,3-year-old xathian was Obtained as a pale yellow oil.

(vi) 5-t-butyl-2(a)-ethoxy-2(e)-methyl-1,3-year-old A solution containing 0.78 g of xathian in 10 mβ of dichloromethane was heated to 0°C. 0.37 g of trimethylsilyl cyanide was added under a nitrogen atmosphere, and then Then, 0.025 g of boron trifluoride ether complex compound was added dropwise, and this solution was left overnight. and warmed to room temperature. Dilute this yellow solution with ether and dissolve the sodium bicarbonate solution. Washed with liquid and brine, dried over sodium sulfate and evaporated under vacuum. residue Chromatography using alumina (eluent: hexane containing 2% ether) Therefore, it was purified. 5(e)-t-butyl-2(e)-methyl-1,3-oxathi 0.51 g of an-2(a)-carbonitrile was obtained as a pale yellow oil.

Takumi Hiroshi 5e-t-butyl-2e-methyl-1,3-dithiane-28-carbonide Dry acetonite containing 0.5 g of sodium oxide acetate 5(e)-t-butyl-2(e)-methyl-1,3-dithi in Ryl 30mj2 To a stirred solution containing 0.2 g of an-2(a)-carbonitrile, 0.19 g of lorperbenzoic acid (85% purity) was added. Bring the resulting mixture to room temperature The insoluble material was then removed by filtration and diluted with ethyl acetate. Washed. The resulting filtrate was dried over magnesium sulfate and evaporated under vacuum.

The residue was purified by column chromatography on silica. Hexane/ 5(e)-tert-butyl-2(e )-Methyl-1,3-dithiane-2(a)-carbonitrile-1(e)-oxy 0.17 g of do was obtained as a white solid.

5(e)-t-butyl-2(e)-methyl-1,3-oxathian-2(a)- In a similar manner starting from carbonitrile, 5(e)-t-butyl-2(e)- Methyl-1,3-year-old xathian-2(a)-carbonitrile-3(a)-oxy and 5(e)-t-butyl-2(e)-methyl-1,3-oxathian-2( a)-Carbonitrile-3(e)-oxide was prepared.

5e-t-butyl-2e-methyl-1,3-dithiane-28-carbonide 1-1,1-dioxide 5(e)-t-butyl-2(e)-methyl-1,3- Dithiane-2(a)-carbonitrile-1(e)-oxide 0.35g and sulfuric acid A stirred mixture of 1 g of magnesium in 15 rnJ2 of acetone was added with filtrate. 0.36 g of potassium manganate was added. The resulting mixture was kept at room temperature for 4 hours. Then, it was filtered using Celite. The colorless filtrate was evaporated under vacuum to give 5( e) -t-butyl-2(e)-methyl-1,3-dithiane-2(a)-carbonylate 0.33 g of tolyl-1,1-dioxide was obtained as a white solid.

■１ 5e-t-butyl-2e-methyl-1,3-oxathian-2a-carbo Nido 1-3,3-dioxide 5(e)-t-butyl-2(e)-methyl-1, 100 mg of 3-oxathian-2(a)-carbonitrile and monoperoxif Contains 0.28 g of magnesium tartate in 20 mβ of ethanol and 10 mβ of water. The resulting mixture was heated to reflux for 2 hours. The ethanol was removed under reduced pressure and the product was evaporated. extracted with ether, washed with brine, dried over magnesium sulfate, and the solvent was removed under vacuum. Removed. The residue was subjected to column chromatography using silica (the eluent was ether). and hexane in a ratio of 1:4). 5(e)-t-butyl -2(e)-methyl-1,3-oxathian-2(a)-carbonitrile-3, 37 mg of 3-dioxide was obtained as a white solid.

Anal communication 1: 1.1 IA Compound of formula (I) 10.00 Alkylphenol ethoxylate” 7.50 alkylaryl sulfone) ”2.5008~CI8 Aromatic Solvent 80.00 Total 100.00 2. Milk “Σ1”” L liquid Compounds of formula (I) io, o.

Alkylphenol ethoxylate 2.50 alkylaryl sulfonate ”2.50 Ketone Solvent 64.00 C- to C+s aromatic solvent 18.00 Antioxidant 3.00 3.1!13 Compound of formula (I) 5.00 Cs ~ C+s aromatic solvent 7.00 C+a aromatic solvent 28.00 China clay 10.00 Alkylaryl sulfonate 1.00 Naphthalene sulfonic acid 3.00 Diatom±46.00 Total 100.00 4, #M Compound of formula (I) 0.50 Talc 99.50 Total 100.00 5, ILjl Compound of formula (I) 0.50 Sugar 79.50 Parafine wax 20.00 6. Emulsion Compound of formula (I) 5.00 C@~C1, aromatic solvent 32.00 Cetyl alcohol 3.00 POEGMO” 0.75 POESE”・”0.25 Silicone solution 0.10 Water 58. 90 Total 100.00 7.1e1 亙” Compound of formula (I) 10.00 Alkylaryl ethoxylate” 3.00 Silicone solution 0.10 Alkanediol 5.00 Humid silica 0.50 Xanthan gum 0.20 Water go, o.

Buffer 1.20 Total ioo, o.

8. Microemulsion Compounds of formula (I) to, o.

POEGMO” 10.00 Alkanediol 4.00 Wednesday 76, 00 9. Medical game Jba11 1 Compound of formula (I) 70.00 Polyvinylpyrrolidone 2.50 Alkylaryl ethoxylate ″″ 1.25 alkylaryl sulfonate ”　1.2510.1 plate 1 Compound of formula (I) 2.00 Alkylphenol ethoxylate” 5.00 Alkylaryl sulfonate ”3.00C, -C, aromatic solvent 20.00 Diatomaceous earth granules 70.00 Compound of formula (I) 0.3 Piperonyl butoxide 1.5 C1-C+s saturated hydrocarbon solvent 58.212, aerosol Compound of formula (I) 0.30 0.~C11 Saturated Hydrocarbon Solvent 10.00 Sorbitan Monooleate" 1. 00 water 40. 00 Butane 48.70 Compound of formula (I) 1.00 CO* 3. QQ POEGMO” 1.40 Propanone 38.00 Water 56. 60 Total 100.00 14.1 engineering left 21 Compound of formula (I) 2.50 Resin 5.00 Antioxidant 0.50 Highly aromatic white spirit 92.00 total 100.00 15, W mouth Compound of formula (I) 0.10 Antioxidant 0.10 Odorless kerosene 99.80 16.10 Compound of formula (I) 0.10 Piperonyl butoxide 0.50 Antioxidant 0.10 Odorless kerosene 99.30 Total 100.00 17. Microcapsule Compounds of formula (I) io, o.

Cs ~ C+-Aromatic Solvent 10.00 Aromatic Diisocyanate)” 4.50 Alkylphenol ethoxylate” 6.00 Alkyldiamine-1,00 Diethylenetriamine 1.00 Concentrated hydrochloric acid 2.20 Xanthan gum 0.20 Humid silica 0.50 Water 64. 60 Total 100.00 (note) *Surfactant # Things that react to form the polyurea wall of microcapsules +1: POEGMO = polyoxyethylene glycerol monooleate +2: POESE = polyoxyethylene sorbitan ester The antioxidant may consist of any of the following or mixtures thereof.

Butylated hydroxytoluene Butylated hydroxyanisole Vitamin C (ascorbic acid) ! 1 main group 1 The following examples illustrate in a non-limiting manner the pesticidal activity of compounds of formula (I). .

11 stars 1 The activity of compounds of the invention was tested as follows. That is, the compound is placed in acetone. Dissolve (5%), then water and synperonic (5%) ( (94.5%=0.5%) to form an aqueous emulsion. Using this solution The following insects were treated using

Musca domestica: Wrap each end with gauze Twenty female musks were placed in a covered cardboard tube. locked up like this Insects were sprayed with a solution of the compound and mortality was determined after 48 hours at 25°C.

Compounds 6.12 and 13 were active at less than 11000 pp.

Plutella xylostella Plutella x 1ostella: 10 animals Plutella larvae were placed on circular pieces of leaves and sprayed with a solution of the compound. at 25℃ After 2 days, mortality was determined.

Compounds 1.2.3 and 5 were active below lo00 ppm.

Mzus ersicae: 10 adults were placed on Chinese cabbage leaves. placed on a circular piece of. After 24 hours, a solution of the compound was sprayed onto the circular pieces. 25℃ After 2 days, mortality was determined.

Compounds 11.12 and 13 were active below 11000 pp.

Compounds 3.7 and 10 were active at less than 200 ppm.

Diabrotic Power Undecim Punk - Diabroticaundecim unctata Filter paper and food were sprayed with a solution of the compound. Next, 10 second cotton larvae were placed on this filter paper. made me grow. Mortality was determined after 48 hours.

Compound 4 was active at less than 11000 pp.

Compounds 1.2.3.5.11.6.7.9.8.10.12 and 13 are 200p It was active below pm.

Kanoyo person Shaved λ5 ■1 leave No. 1 hill person Additional 9 special characteristics f2 international search report Fffffi PCT/1yJ210 +111P+1-Seal n111'mton+2 11・PM+21+011/l1 International Search Report

Claims (16)

[Claims] 1. The following formula (I) for the effective amount of pests as a pest control agent: ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) [In the formula, Y is oxygen or the group S(O)m Yes, m and n are selected from 0, 1 and 2, respectively, and R2a and R2b are the same cyano, nitro, methyl (optionally halo), respectively. may be substituted with gen), the group S(O)qR7 (where q is 0, 1 or 2 and R7 is methyl or ethyl) or group COR8 {Here, R8 is hydrogen, hydroxyl, C1-C4 alkoxy, C1-C4 alkoxy (optionally substituted with fluoro) or the group NR9R10 (where R 9 and R10 are each selected from hydrogen, methyl or ethyl) is} selected from R4a, R4b, R5a and R5b each represent hydrogen, methyl, cyano or triphenium. R5a and R5b are selected from fluoromethyl, R5a is a C2-C5 first, A secondary or tertiary alkyl group (optionally halogen, C1-C4 alkoxy or optionally substituted with C3-C4 cycloalkyl group), C1-C4 alkoxy or is a C3-C4 cycloalkyl group, and R5b is hydrogen, hydroxyl, C1- C4 alkoxy, C1-C4 alkanoyloxy or C1-C4 alkyl (optional) may be substituted with alkoxy), or R5a and R5b are ge m-dimethyl groups or combined together with the ring carbon to which they are attached 3- to 5-membered ring {optionally containing heteroatoms or olefinic bonds; and optionally a C1-C4 alkyl group (optionally substituted with halogen). may be substituted] pest control consisting of contacting with a compound having 8 to 30 carbon atoms of Method. 2. 2. The method of claim 1, wherein Y is oxygen or sulfur. 3. R2a and R2b may be the same or different, and each represents methyl, Claim 1 or 2 selected from ethyl, cyano or trifluoromethyl The method described in section. 4. 4. The method of claim 3, wherein R2a is methyl. 5. 4. The method of claim 3, wherein R2b is methyl or cyano. 6. R4a, R4b, R5a and R5b are each selected from hydrogen or methyl; 6. The method according to any one of claims 1 to 5. 7. C2-C5 second or third group where R5a is optionally substituted with fluoro 3 alkyl group or cyclopropyl group, any one of claims 1 to 6 Method described. 8. Any one of claims 1 to 7, wherein R5b is hydrogen, methyl or ethyl. The method described in. 9. The following formula (I): ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) {In the formula, Y, R2a, R4a, R5a , R5b, R6b, m and n are as described in claim 1, and R2b is ano, nitro, group S(O)qR7, group COR8 (where R7 and R8 are As stated in scope 1) or a C1-C8 alkyl group substituted with halogen} compound. 10. Next name: ・5(e)-t-butyl-2(e)-methyl-1,3-dithiane-2(a)-ka Rubonitrile ・5(e)-t-butyl-2(a)-methyl-1,3-dithiane-2(e)-ka Rubonitrile ・5(e)-t-butyl-2(e)-methyl-1,3-dithiane-2(a)-ka Rubonitrile-1(e)-oxide 5(e)-t-butyl-2(e)-methyl -1,3-dithiane-2(a)-carbonitrile-1,1-dioxide 2(e )-Methyl-5(e)-(1-methyl-2,2,2-trifluoroethyl)-1 ,3-dithiane-2(a)-carbonitrile ・5(e)-cyclopropyl-2(e)-methyl-1,3-dithiane-2(a) -Carbonitrile ・5(e)-t-butyl-2(e)-methyl-1,3-oxathian-2(a) -Carbonitrile ・5(e)-t-butyl-2(e)-methyl-1,3-oxathian-2(a) -Carbonitrile-3(a)-oxide 5(e)-t-butyl-2(e)-methane Thyl-1,3-oxathian-2(a)-carbonitrile-3(e)-oxide ・5(e)-t-butyl-2(e)-methyl-1,3-oxathian-2(a) - Compounds selected from those of carbonitrile-3,3-dioxide. 11. The following formula (I): ▲There are mathematical formulas, chemical formulas, tables, etc.▼A method for producing the compound (I), (i) The following formula (II): ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II) (In the formula, X is SH, Y1 is SH or OH) A suitable aldehyde or compound with the formula ▲Mathematical formula, chemical formula, table, etc.▼ or their reactive derivatives (wherein the 2, 4, 5 and 6 positions R-based substituents are as described in claim 1 or 9), then as necessary oxidize one or two ring sulfur atoms, or Or (ii) one of R2a and R2b is cyano and the other is substituted with halogen; When it is an alkyl group that may be (a) Following formula (III): ▲There are mathematical formulas, chemical formulas, tables, etc.▼Compound of (III) and an alkylating agent, or (b) The following formula (IV): ▲There are mathematical formulas, chemical formulas, tables, etc.▼(IV) (In the formula, R11 is C1-C4 alkyl (R12 is methyl which may be substituted with halogen) and trialkylsilyl cyanide in the presence of an acid catalyst. The method comprising: 12. Control of pests on plants and/or stored products and/or the environment A method of preparing an effective amount of formula (I) according to any one of claims 1 to 9. compounds on plants and/or stored products and/or environments that are susceptible to pests. said method, comprising administering to said person. 13. An effective amount of a compound of formula (I) according to any one of claims 1 to 9 is administered to an animal. A method of controlling pests in animals, which consists in administering the substance to the animal. 14. One or more compounds of formula (I) according to any one of claims 1 to 9 A pesticidal composition comprising in admixture with a carrier or diluent. 15. The compound according to claim 14, which additionally contains a synergist or a drug efficacy enhancer. Pesticide composition. 16. One or more pest control active ingredients, attractants, repellents, bactericides, fungicides and The harmful substance according to claim 14 or 15, which additionally contains an anthelmintic and/or anthelmintic. Biocidal composition.