JPH03197473A - New thiadiazine derivative, its production and insecticide and acapicide containing the same compound - Google Patents

Abstract

NEW MATERIAL:Tetrahydro-1,3,5-thiadiazine-4-ones expressed by formula I (R<1> is H or 1-4C alkyl; R<2> is 1-4C haloakyl) or salts thereof. EXAMPLE:2-(2,2,3,3,3-Pentafluoro-n-propylimino)-3-(4-tertbutylbenzyl)- 5-phenyl- tetrahydro-1,3,5-thiadiazine-4-one. USE:An insecticide and acaricide, capable of exhibiting a wide insecticidal spectrum and having excellent insecticidal activity even against insect pests of the order Lepidoptera. PREPARATION:A carbamoyl chloride derivative expressed by formula II is made to react with a thiourea derivative expressed by formula III in a solvent such as THF at 30-250 deg.C for 0.1-30hr to afford the compounds expressed by formula I.

Description

[Detailed Description of the Invention] [Industrial Application Field] The present invention is directed to the use of general formula (I) in which the no-4-ones have insecticidal and acaricidal effects, Japanese Patent Publication No. 3083/1983, 1970-12
No. 390 and Kokai No. 54-154780.

Among these, tetrahydrocarbons represented by the formula (TV) (1) (wherein, R1 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and R2 represents a haloalkyl group having 1 to 4 carbon atoms) -1°3.5-Thiadiazin-4-ones or salts thereof, methods for producing them, and insecticides and acaricides characterized by containing one or more of them as active ingredients.

The compounds of the present invention are useful in various industrial fields, and are particularly useful in the agricultural field as insecticides and acaricides.

[Conventional technology]

Conventionally, 2-tert-butylimino-3isopropyl- represented by tetrahydro-1,3,5-thiadiazidi
5-phenyl-tetrahydro 1.3.5-thiadiazin-4-one (-Ship name: Buprofezin: Buprof
ezin) is in practical use as an insecticide. Furthermore, in Japanese Patent Publication No. 140577/1987, tetrahydro-1,3 5-Thiadiazin-4ones are new compounds with insecticidal and acaricidal effects, especially 2
Tetrahydro-1,3,5-thiadiazin-4-ones in which at least one or more of the -imino group or the 3-position is WtfA-treated with a certain substituted phenylalkyl group are remarkable compared to the known compound buprofezin. There is a description that it exhibits insecticidal and acaricidal effects. However, these insecticides and acaricides have insecticidal activity against Hemiptera pests and Coleoptera pests, but do not have sufficient insecticidal activity against Moptera pests. There is a need for the development of a new drug that has similar effects to these insecticides and acaricides and has excellent insecticidal activity against Lepidoptera pests.

[Problem to be solved by the invention]

An object of the present invention is to provide an excellent insecticidal compound, insecticide, and acaricide having a new structure, a wide insecticidal spectrum, and high insecticidal activity, which solve the problems of the prior art, and a simple method for producing the same. do.

[Means and effects for solving the problem] In order to solve the above problem, the present inventors conducted intensive studies on tetrahydro-1,3,5-thiadiazin-4-ones, and found that 2-
(l-Methyl-2゜2.2-trifluoroethylimino)-tetrahydro-13,5-thiadiazin-4-ones or their salts have a wide insecticidal spectrum, and known related compounds do not show sufficient insecticidal activity. We have completed the present invention by discovering that it has high insecticidal activity even against harmful Lepidoptera pests.

That is, the present invention provides a tetrahydrocarbon compound represented by the general formula (1) (wherein R1 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and R2 represents a haloalkyl group having 1 to 4 carbon atoms). 1.3.5-Thiadiazin-4-ones or salts thereof, a compound represented by the general formula (n) (wherein, R1 has the above-mentioned meaning), is converted into a compound represented by the general formula (Iff, ) (wherein, A method for producing tetrahydro-1,3,5-thiadiazin-4-ones or salts thereof represented by the general formula (), which comprises reacting the compound with a compound represented by R2 having the above meaning. An insecticide or acaricide containing one or more of tetrahydro-1,3,5-thiadiazin-4-ones represented by the general formula (r) and their salts as an active ingredient. be.

-C Tetrahydro-1°3.5- represented by formula (I)
Thiadiazin-4-ones and their salts have not been described in any literature and are new compounds.

When the 3-position imino group which is a substituent on the thiadiazine ring in the compound of the present invention represented by general formula (I) is a haloalkyl group, the halogen atom is preferably a bromine atom, a chlorine atom or a fluorine atom, particularly A fluorine atom is preferred. As the haloalkyl group, fluoromethyl group,
Difluoromethyl group, trifluoromethyl group, 2,2.
3.33-pentafluoro-normal-propyl group, 2
．． 2,3,3.4.4.4-hebutafluoronormal-
Butyl group is preferred. Further, as a substituent for the 5-position phenyl group which is a substituent of the thiadiazine ring, a methyl group is preferable as the alkyl group, and a methyl group substitution at the 4-position is particularly preferable.

-i Examples of salts of the compound of the present invention represented by formula (I) include hydrochloride, hydrobromide, hydroiodide, hydrofluoride, sulfate, hydrogen sulfate, nitrate, chlorine acid salts, perchlorates, phosphates, hydrogen phosphates, dihydrogen phosphates,
Inorganic acid salts such as thiocyanate, tetrafluoroborate, formate, acetate, trichloroacetate, trifluoroacetate, citrate, lactate, oxalate, glycolate, malonate, succinate Examples include organic acid salts such as acid salts, malates, dodecylbenzenesulfonates, benzoates, salicylates, and nicotinates.

Next, representative examples of the compounds of the present invention represented by general formula (I) are shown in Table 1, but the present invention is not limited thereto.

Table 1 (1) 41h -CH2 CH2CFzCF3 CH2CF2CF3F3 CH2CF2CF3 CH2CF2CFzCF+ The compound of the present invention represented by general formula (I) can be produced by the following method.

(n) ([1) (1) In formula C, R' and R'' have the above meanings.) That is, -i a carbamoyl chloride derivative represented by formula ('II) and a carbamoyl chloride derivative represented by formula (III) It can be obtained by reacting with a thiourea derivative in the absence or presence of a solvent, preferably in the presence of a solvent. Suitable solvents include acetone, methyl ethyl ketone, cyclohexanone, tetrahydrofuran, dioxane, ethyl ether, benzene, toluene, Acetonitrile, ethanol, propatool, dichloromethane, chloroform, carbon tetrachloride, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, 1,3-dimethyl-2=imidazolidinone, water and other solvents that do not affect the reaction may be used. I can do it.

The reaction is carried out with heat or in the presence of a base. When the reaction is carried out by heating, the reaction temperature can be varied over a wide range depending on the starting materials;
0'C, preferably 40-150'C.

The reaction time is 0.1 to 30 hours, preferably 0.5 to 2 hours.
It is 4 hours. When carrying out the reaction using a base, suitable bases include potassium hydroxide, sodium hydroxide,
potassium carbonate, sodium carbonate, sodium bicarbonate,
Examples include triethylamine, pyridine, NN-dimethylaniline, 1,8-diazabicyclo-[5,4,O]-7-undecene, and the like. The reaction temperature and reaction time can vary over a wide range depending on the starting materials, but - for boat fishing the reaction temperature is -10 to 200°C, preferably room temperature to 150°C, and the reaction time is 0.1 to 30 hours. , preferably 0.5 to 24 hours.

In carrying out the reaction related to the present invention, the general formula (I[)
A carbamoyl chloride derivative represented by the formula (I[l
The thiourea derivatives represented by ) may be used in equimolar amounts or in a slight excess of either one.

When performing a reaction using a base to obtain the compound represented by the general formula (1) in a free form, it is preferable to use the base in an amount twice the molar amount or slightly in excess of the carbamoyl chloride derivative represented by the general formula (■). .

In addition, in the above reaction formula, the carbamoyl chloride derivative, which is the starting compound represented by the general formula (It), can be prepared by a known method (Journal of Organic Chemistry:
Journal of Organic Chemi
39, p. 2897 (1974)). Further, thiourea represented by formula (III) can be synthesized according to a known method.

Salts of the compounds of the present invention represented by general 2N) can be produced according to known methods. In other words, General 2N
) The compound of the present invention represented by ; Organic acids such as formic acid, acetic acid, trichloroacetic acid, trifluoroacetic acid, citric acid, lactic acid, oxalic acid, glycolic acid, malonic acid, succinic acid, malic acid, dodecylbenzenesulfonic acid, benzoic acid, salicylic acid, nicotinic acid, etc. It can be produced by treatment with a desired acid.

The compound of the present invention represented by general formula (1) can be used in agriculture, forestry,
It can be used to protect plants from a wide variety of harmful arthropods encountered in fields such as horticulture.

For example, brown planthopper, brown planthopper, brown planthopper, black leafhopper, white leafhopper, brown leafhopper, white leafhopper, whitefly, whitefly, green peach aphid, cotton aphid, radish aphid, snowy white aphid, dung beetle, red stink bug, red stink bug Hemipteran stink bugs, spider-edge stink bugs, white stink bugs, southern stink bugs, green stink bugs, San Jose scales, and scrub scales, etc.
iptera) Pests, Japanese leafhopper moth, Kubnomoth, Japanese leafhopper moth, Inetbug, Futaobikoyaga, Golden leaf moth, Kumananaginowaba, Tamanayaga moth, Kaburaya moth, Apple leafminer moth, Peach leaf moth, Citrus leafminer moth, Nasichibigiga moth, Kosuka moth, Gypsy moth, American white-wing moth, Diamondback moth, Army armyworm, Armyworm moth, Sparrow moth Tow, Lepidoptera (Lepidoptera) such as the butterfly
era) Pests, Coleoptera (Lepidoptera) such as the brown beetle, the brown beetle, the beetle beetle, the rice beetle, the rice weevil, and the rice weevil
Ptera) Pests, Yellow-bellied gumbo, Soybean pod fly, Curtain fruit fly, Citrus fruit fly, Rice fruit fly,
Onion leafminer fly, eggplant leafminer fly, onion leafminer fly,
Diptera pests such as seed flies, Thripsidae such as tea thrips, southern yellow thrips, and black thrips, two-spotted spider mites, Kanzawa spider mites,
It is effective against mites such as false red spider mite, orange spider mite, apple spider mite, white spider mite, and teal spider mite.

In addition to the above fields, there are also various pests that cause harm to humans and livestock by transmitting infectious diseases, sucking blood, biting, causing dermatitis, etc., such as Culex pipiens, Culex pipiens, Culex pipiens, Aedes albopictus, Houseflies, Sentinic fly, giant black fly, black fly, fruit fly melanogaster, American cockroach, German cockroach, black cockroach, black cockroach, Japanese cockroach, house dust mite, body lice, head lice, bed bugs, human flea, dog flea, cat flea, brown moth, brown moth, blue lizard moth, green leaf comb In addition, pests that damage food and stored grains, such as woolly mites, staghorn weevils, red bean weevils, black-and-white beetles, and cypress moths, as well as furniture, building materials, books, clothing, etc. Pests that cause damage to the plant, such as the Japanese termite, Japanese termite, Japanese yellow beetle, Japanese snail beetle, Japanese burr, and Japanese snail beetle, as well as so-called unpleasant pests such as the Japanese midge fly, the Japanese midge, the Japanese midge, the Japanese stink bug,
It is also useful for preventing damage from a wide variety of harmful arthropods, such as spiny beetles, yellow millipedes, pill bugs, and woodlice. In particular, the compounds of the present invention exhibited remarkable insecticidal activity against Lepidoptera pests compared to known compounds.

When the compound of the present invention is actually applied, it can be used alone without the addition of other ingredients, but in order to make it easier to use as a pesticidal agent, it is generally applied with a carrier added thereto. The compounds of the present invention can be formulated into emulsions, wettable powders, powders, granules, fine granules, oils, and other formulations using methods well known in the art in the same manner as for general M drugs, without requiring any special conditions. 5 and can be used for various purposes depending on the purpose.

Carrier here means an inorganic or organic substance, synthetic or natural, which is incorporated to aid in the delivery of the active ingredient to the area to be treated and to facilitate storage, transport and handling of the active ingredient compound. .

Suitable solid carriers include clays such as montmorillonite and kaolinite; inorganic substances such as diatomaceous earth, clay, talc, vermiculite, gypsum, calcium carbonate, silica gel, and ammonium sulfate; vegetable organic substances such as soybean flour, sawdust, and wheat flour; Examples include urea.

Suitable liquid carriers include aromatic hydrocarbons such as toluene, xylene and cumene; paraffinic hydrocarbons such as kerosene and mineral oil; halogenated hydrocarbons such as carbon tetrachloride, chloroform and dichloroethane; acetone and methyl ethyl ketone. Ketones, dioxane, ethers such as tetrahydrofuran; methanol, ethanol,
Examples include alcohols such as propanol and ethylene glycol; dimethylformamide, dimethyl sulfoxide; and water.

Furthermore, in order to enhance the efficacy of the compound of the present invention, the following adjuvants may be used individually or in combination depending on the purpose, taking into consideration the dosage form of the preparation, the application situation, etc.

For purposes such as emulsification, dispersion, spreading, wetting, binding, and stabilization, lignin sulfonates, alkylbenzenesulfonates,
Anionic surfactants such as alkyl sulfate; polyoxyalkylene alkyl ether, polyoxyalkylene alkylaryl ether, polyoxyalkylene alkyl amine, polyoxyalkylene alkyl amide,
Nonionic surfactants such as polyoxyalkylene alkylene thioether, polyoxyalkylene fatty acid ester, glycerin fatty acid ester, sorbitan fatty acid ester, polyoxyalkylene turbicun fatty acid ester, polyoxypropylene polyoxyethylene block polymer; calcium stearate, Lubricants such as wax; stabilizers such as isopropylhydrodiene phosphate; and others such as methyl cellulose, carboxymethyl cellulose, casein, and gum arabic. However, these components are not limited to those mentioned above. Furthermore, two or more of these compounds of the present invention can be used in combination to exhibit even more excellent insecticidal power. Also, for example, fenthion, fenitrothion, diazinon, chlorpyrifos, chlorpyrifos-methyl, methidathion, dichlorpos, thiometone, acephate, trichlorfone, inxathion, pyridafenthione, salithion, prothiophos, propafos, EPN, sulprofos,
NACSMTMC, MI PCXBPMC, PHC,
MPMC, XMC, pirimicarb, carbosulfan,
benfuracarb, methomyl, oxamyl, pyrethrin,
Tetramethrin, phthalthrin, paperthrin, allethrin, resmethrin, fenvalerate, esfenvalerate, vermethrin, cypermethrin, fluhalinate, etofenbrox, fluhalinate, dihalothrin, bifenthrin, diflubenzuron, chlorofluazuron, teflubenzuron, flufenoxuron, cibronzin, buprofezin, fenoxycarb, penzoepin, neraistoxin, bensultap,
Insecticides, acaricides and other insecticides, acaricides or fungicides such as thiocyclam, avermectin, dicofol, amitraz, polynactin complex, fenbutastin oxide, tricyclohexyltin hydroxide, hexythiazox, flubenzamine, triaracene, clofentezine, milbemycin. agents, nematicides, herbicides, plant growth regulators,
By mixing it with fertilizers, machine oil, other agricultural chemicals, etc., it is possible to create a multipurpose composition with even greater efficacy, and a synergistic effect can also be expected. The compound of the present invention is stable against light, heat, oxidation, etc., but if necessary, antioxidants or ultraviolet absorbers, such as BHT (2,6-di-t-butyl-4-methylphenol), BHA (9 By adding appropriate amounts of phenol derivatives such as (butylhydroxyanisole), bisphenol derivatives, arylamines such as phenyl α-naphthylamine, phenyl-β-naphthylamine, condensates of phenetidine and acetone, or benzophenone compounds as stabilizers, A composition with more stable effects can be obtained.

The insecticide and acaricide according to the present invention contains the compound as an active ingredient in an amount of 0.1 to 95% by weight, preferably 0.3 to 50% by weight. To apply the insecticide and acaricide of the present invention,
Generally, it is desirable to use the active ingredient at a concentration of 0.01 to 5,000 ppm, preferably 0.1 to 11,000 ppm. In addition, the application amount per 10a is generally 1 for the active ingredient.
g to 300 g.

[Example] Next, the method for synthesizing the compound of the present invention will be explained by giving Examples of the compound of the present invention represented by the -i formula (1), but the present invention is not limited thereto.

Example 1. 2-(2,2,3,3,3-penta0fluoro-normal-propylimino")-1-(4-
Synthesis of tertiary-butylbenzyl)-5-phenyl-tetrahydro-1,3,5-thiadiazin-4-one (compound No. 1).

1.3. In a solution of 1.05 g of 5-1-riphenylphexahydro-S triazine dissolved in 20 ml of tetrahydrofuran, 1.00 g of trichloromethyl chloroformate was dissolved in 20 d of benzene while stirring at room temperature and under a nitrogen stream. The solution was added dropwise. The reaction solution was stirred at room temperature for 1.5 hours. Next, 3.54 g of 1-(4-couchary-butylbenzyl 13-(2,2,33,3-pentafluoro-n-propyl)thiourea) were added under stirring at room temperature, followed by 4.0 g of triethylamine. ml and stirred at room temperature for 6 hours. 50 ml of water was added to the reaction solution and extracted with 200 ml of ethyl acetate. The ethyl acetate solution was washed with water, dried, and the ethyl acetate was distilled off under reduced pressure to obtain an oil. The product was purified by column chromatography (silica gel, developing solvent: hexane-ethyl acetate (9:1)) to obtain the desired 2-(2,2,3,3,3-pentafluoro-n-propylimino)-3- (4-tert-butylbenzyl) 5 phenyl-tetrahydro-1,3,5-thiadiazin-4-one 0.10
I got g. Refractive index n, 20=1°5271 eat I Rv (cm-'): 1680.1605.1
495.1440, river ax 1380, 1350.1280.1190.1125.
1085.1075.1005°MS 3.80 (2H, t, J=14Hz), 4.77 (2H
, s), 5.28 (21+, s), 7.00-7.60
(9H, m).

Example 2. 2-(2,2,3,3,4,4,4hepfluoron-butylimino)3-(4-tert-butylbenzyl)-5phenyl-tetrahydro-1,3,5-thiadiazine-4 -one (compound No.
, 2) synthesis.

1.3.5-) To a solution of 1.82 g of Ripheny-hexahydro-S triazine dissolved in 20 ml of tetrahydrofuran, 1.71 g of trichloromethylchloroforme was dissolved in 10 ml of benzene while stirring at room temperature and under a nitrogen stream. The solution was added dropwise. The reaction solution was stirred at room temperature for 1.0 hour. Next, 3.50 g of 1-(4-tert-butylbenzyl)-,3-(2,2,3°3.4,4.4-heptafluoro-normalfuthyl)thiourea was added under stirring at room temperature. Then, 15% of a 10% aqueous sodium hydroxide solution was added, and the mixture was stirred at room temperature for 6 hours.

50 d of water was added to the reaction solution, and the mixture was extracted with 200 ails of ethyl acetate. After washing the ethyl acetate solution with water and drying, ethyl acetate was distilled off under reduced pressure, and the obtained oil was purified by column chromatography (silica gel, developing solvent: hexane-ethyl acetate (10:1)) to obtain the desired 2 - (2,2,,3゜3.4,4,4-heptafluoro-n-butylimino)-3-(4-tert-butylbenzyl)-
0.86 g of 5-phenyl-tetrahydro-1°3.5-thiadiazin-4-one was obtained.

Melting point; 123.7-125.3°C Br I Rv (cm-'): 1665.1610.1
490.1455, ax 1390.1350.1285.1225.1170.
1115.1090.1000, 3 910.880.11100°MS 3.94 (2) 1. t, J=17Hz), 4.87(
28, s), 5.32 (2) 1. s), 7.28-7.
44 (9H, m), (100MHz) Next, an example of producing the starting material for the compound of the present invention will be shown below.

Reference example 1. Synthesis of 1-(4-tert-butylbenzyl)-3-(2,2,3,3,3-pentafluoro-normal-propyl)thiourea.

4-tert-butylbenzyl isothiocyanate 6
．． 5 g and 5.0 g of 2,2,3,3,3-pentafluoroethylamine were dissolved in 30 ra of ethyl acetate.
It was left for 4 hours. Ethyl acetate was distilled off under reduced pressure, and the obtained white crystals were washed with hexane to obtain the desired 1-(4-tert-butylbenzyl)-3-(2,2,3,3,3
-pentafluoro-n-propyl)thiourea9.
2g was obtained.

Melting point i 91.0-92.5°C 4 eat IRv (cm-'): 3250.3070.2
950.1560.1525aX 1400.1365.1345.1275.1190.
1115.1035.1015°MS 4.36 (2H, m), 4.50 (2) 1. s), 5.
40-6.20 (2H, s), 7.27 (2H, d,
J=8Hz), 7.41 (2)1. d, J
=8Hz).

Reference example 2. Synthesis of 1-(4-tert-butylbenzyl)-3-(2,2,3,3,4,4,4-butafluoro-n-butyl)thiourea.

4-Tertiary-butylhensyl isothiocyanate 4
．． 95 g and 5.0 g of 2.2,3.3,4,4.4-hebutafluoro-n-butylamine were added to 30 g of ethyl acetate.
d and left at room temperature for 24 hours.

Ethyl acetate was distilled off under reduced pressure, and the obtained white crystals were washed with hexane to obtain the desired 1-(4-tert-butylbenzyl)=3-(2,2,3,3゜4.4.4 6.15 g of -hebutafluoro-n-butyl)thiourea were obtained.

Melting point; 78.5-80.0°C 13B5.1365.1355.1345.1290.
12B0.1230.1220.1210.1175.
1110.910°MS 4.0-4.8 (4H, m), 5.5-6.0 (18,
s), 6.1 to 6.8 (LH, s), 7.19 (2H
, d, J=8Hz), 7.34(2H, d, J=8Hz
), (100MHz) Next, the formulation containing the compound of the present invention represented by the general formula (1) as an active ingredient and the formulation method of the insecticide according to the present invention will be specifically explained using formulation examples. is not limited to these.

Formulation example 1. Emulsion Compound of the present invention・・・・・・・・・・・・・・・・・・
・10 parts Tsurupol 355S・・・・・・・・・・・・
・・・・・・10 parts (Toho Chemical registered trade name) Xylene・・・・・・・・・・・・・・・・・・・・・
...Dissolve and mix 80 parts or more to obtain an emulsion.

Formulation example 2. Wettable powder Compound of the present invention・・・・・・・・・・・・・・・・・・
20 parts Sodium ligninsulfonate 10 parts Sodium alkylnaphthalene sulfonate 5 parts White carbon 5 parts
Diatomaceous earth・・・・・・・・・・・・・・・・・・
...60 parts or more are uniformly mixed and pulverized to obtain a wettable powder.

Formulation example 3. Powder 3 parts of the compound of the present invention are dissolved in 10 parts of acetone, 87 parts of clay for powder are added, and then the acetone is exploded to obtain a powder.

Formulation example 4. Granules 3 parts of the compound of the present invention, 1 part of sodium ligninsulfonate, 20 parts of talc and 76 parts of bentonite are mixed, an appropriate amount of water is added and kneaded, then granulated and dried to obtain granules.

Formulation example 5. Poison bait 1 part of the compound of the present invention, 5 parts of sand YIM, 50 parts of bran, 20 parts of rice bran, and 24 parts of wheat flour are mixed, an appropriate amount of water 7 is added, kneaded, granulated and dried to obtain a poison bait.

Next, in order to clarify that the compounds of the present invention have excellent insecticidal activity, the following test examples will be specifically explained. Furthermore, all tests were conducted in triplicate, and the results are shown as the average value.

Test example 1. Effect on Spodoptera trifoliata The emulsion prepared according to Formulation Example 1 is diluted with water to a concentration of 500 ppm, and the leaves of Citrus orchid are immersed. After air-drying, transfer the treated leaves to a plastic cup and place the 2nd instar larva of Spodoptera japonica 1.
The mortality rate was investigated 5 days after feeding each animal. The results are shown in Table 2. Comparison compound (a) Japanese Patent Application Publication No. 1983 (1986)
A compound described in No.-140577.

8 Comparative compound (b) Generic name dichlorvos (DDVP) (CH30)z P Ofj+=ccI□ Comparison compound (c) Compound (generic name Buprofezin) described in Japanese Patent Publication No. 54-3083 (generic name Buprofezin) CH3 Table 2 Spodoptera spp. Effect test example 2. Effect on diamondback moth The emulsion prepared according to Formulation Example 1 was diluted with water to a concentration of sooppm and sprayed on a potted Orchid seedling (5-6 leaf stage) using a hand sprayer to the extent that the chemical solution dripped lightly. The air-dried transplants were cut out and placed in plastic cups, and 10 second-instar diamondback moth larvae were fed, and the mortality rate was examined 5 days later. The results are shown in Table 3.

Table 3 Comparative Compounds for Effect on Diamondback Moth (a) Comparative Compound (b) Comparative Compound (c) Table 2 shows that the compounds of the present invention have stronger insecticidal activity than known structurally similar comparative compounds.

Comparative Compound (a) Comparative Compound (b) Comparative Compound (c) Table 3 shows that the compounds of the present invention have stronger insecticidal activity than known structurally similar comparative compounds.

Therefore, the above test examples demonstrate that the compounds of the present invention have stronger insecticidal activity against Lepidoptera pests than known structurally similar comparative compounds.

[Effect of the invention 1] As is clear from the above explanation, the tetrahydro-1゜3.5-thiadiazin-4-ones represented by the general formula (1) or the salts thereof according to the present invention are extremely effective against pests. It is a compound that exhibits pesticidal effects. Furthermore, tetrahydro-1,3,5- represented by general formula (1) according to the present invention
Pesticides containing thiadiazin 4-ones or salts thereof have excellent properties and are useful as insecticides.

Claims (3)

[Claims] (1) General formula (I) ▲Mathematical formulas, chemical formulas, tables, etc.▼ (I) (In the formula, R^1 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and R^2 represents a hydrogen atom having 1 to 4 carbon atoms. - 4 haloalkyl group) or a salt thereof. (2) General formula (II) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (II) (In the formula, R^1 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.) General formula (III) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (III) (In the formula, R^2 represents a haloalkyl group having 1 to 4 carbon atoms.) General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) (In the formula, R^1 and R^2 respectively indicate the above meanings.) Tetrahydro-1,3,5- A method for producing thiadiazin-4-ones or salts thereof. (3) General formula (I) ▲Mathematical formulas, chemical formulas, tables, etc.▼ (I) (In the formula, R^1 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and R^2 represents a hydrogen atom having 1 to 4 carbon atoms. ~4 haloalkyl group)) or their salts as an active ingredient. Insecticide and acaricide.