TW305824B - - Google Patents

Description

Printed 3〇5S ^ 4 ------- Five's invention description by the Employee Consumer Cooperative of the Central Sample Falcon Bureau of the Ministry of Economic Affairs (./ The present invention relates to sulfonamide derivatives, its preparation method, and its use as an insecticide Uses. Some hydrazone derivatives have been disclosed for their insecticidal properties (see Japanese Patent No. Sho 54-122261, Sho 56_45452, Hei 2-138246, Hei 3-74356, and Hei 4-1173). However, in various Fields of use, especially at low doses and low concentrations. The activity of these earlier known compounds is not completely satisfactory. The present invention has discovered new sulfonamide derivatives of formula (I),

〇 II / NH —— S —— N II \ R

Where X represents halogen or c 1 -c4 -haloalkyl, ⑴ R1 represents Cl -C4 _yuan group or Cl < 4-from substituted alkyl group, R2 represents hydrogen or Ci-C4_ environment group, and R3 represents hydrogen , Ci-C4-alkyl, Ci-C4-alkoxycarbonyl or Ci-C4-alkyloxycarbonylmethyl. Furthermore, depending on the nature of the substituent, the compound of formula (I) may exist as geometric isomers and / or optical isomers or mixtures of isomers in various combinations. The present invention relates to pure isomers, and also to isomer mixtures. For example, the known hydrazone compounds exist in two isomeric forms, namely, the cis-based paper standard of the General Chinese National Standard (CNS) A4 specification (210x 297 mm) (please read the notes on the back ^ > i Page binding

NH, N

A7 B7 V. Description of the invention (2) and trans. These isomeric forms are represented by the curve between the double bond nitrogen atom and the adjacent nitrogen atom. Moreover, it has been found that the compound of formula (I) is obtained by reacting the compound of formula (K) with the compound of formula (1B), if necessary in the presence of a base, and if necessary in the presence of an inert diluent, / Ο (Π) II,

0-S-R

II 〇 where X and R 1 have the above definition,

0, R ιι /

Cl ——S —N (III) II \ 〇 R3 where R 2 and R 3 have the above definitions. Furthermore, it has been found that compounds of formula (I) are very suitable for controlling harmful animals. They are particularly effective against arthropods. Unexpectedly and surprisingly, the compound of formula (i) according to the invention has very good activity in controlling harmful animals compared to known prior compounds which are structurally very similar, these known prior The compounds are described in, for example, the aforementioned Japanese Patent Laid-Open (published) Zhao 54-122261, Japanese Patent Laid-Open (published) Zhao 56-45452, and Japanese Patent Laid-open Patent Recognition T Guandong County (CNS) 84 specifications (210X 297 mm --- ----- Troubled clothing ------, 玎 ------ Bing-L. (Please read the precautions on the back page first) Printed by the Central Bureau of Economics and Staff Consumer Cooperative

Printed and printed (Published) Ping 2-138246, Japanese Patent Publication License (Public) Ping 3_74356, and Japanese Patent Publication License (Public) Ping 4-1173. Preferred are the compounds of the following formula (I), wherein X represents fluorine, gas, bromine or Cl -c 2-haloalkyl, R1 represents C 丨 -C2-alkyl or c 1 -c2 -_substituted alkyl, R2 Represents hydrogen or Ci-C2-alkyl and R3 represents hydrogen, Ci-C4i, C1-C4-oxocarbonyl or c1-C2-alkoxycarbonylmethyl. Particularly preferred are compounds of the following formula (I), wherein x represents fluorine, gas or trifluoromethyl, R1 represents methyl or trifluoromethyl, R2 represents hydrogen, methyl or ethyl, and R represents hydrogen, methyl, ethyl, Ethyl, n-propyl, isopropyl, n-butyl, methoxycarbonyl, ethoxycarbonyl, third butoxycarbonyl or methoxymethyl. Very particularly preferred are compounds of the following formula (I), wherein x represents fluorine or gas, R1 represents methyl, R2 represents hydrogen and R3 represents ethyl, n-propyl, isopropyl, butyl or methoxypropyl base. As specific examples of the compound of formula (I) according to the present invention, the compounds listed in Table 1 given below can be mentioned. The size of this paper is applicable to the Chinese National Standard (CNS) A4 specification (210x29 * 7mm). * * (Please read the notes on page f ¾¾ this page) ~ A7 B7 5. Description of the invention (4) Table 1

Printed by the Employee Consumer Cooperative of the Central Ministry of Economic Affairs X R1 R? R3 F CH, H CH, U CH, H CH ^ CH, α CH, HH α CH, H CH, Ια CH, H CH, CH, | ci CH, H ΟΗ, ΟΕ, ΟΗ, 1 Cl CH, H CHCCH,), Cl CH, H ch, ch7ch7ch, Cl CH, H CH, -C〇, CH, Cl CH, H CO, -CH, CH, Cl CH, H CO, -C (CH,), F CHX H CH (CH〇, Cl CF, H CII, CF, CH, H CH, Cl CH, CH, CH, Cl CF, H ch (cha CF, CH ^ H Cl CH, CH, CH ^ CH ^ CH; F CHr CH, CH, Cl CH, CH, CH, F CH, H CH, F CH, CH, CH, CH, CH, Cl CH, CH, CH, CIi, CH, Cl CF, H CH, CH, —6 — -------- 袭 ------ ΪΤ ------, ^ (Please read the notes on the back first ΪΙco to write This page) 'This paper scale is applicable to the Chinese National Standard (CNS) A4 specification (210 X 297 · mm) A7 A7 Printed by the Employee Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs

NH, N

B7 5. Description of the invention (5) For example, if 4-fluoro-4'-methanoxybenzophenone hydrazone and N-methyl sulfonamide gas are used as starting materials, the reaction process can be expressed by the following equation : / Formula (Π) provides a general definition of the hydrazone compound used as a starting material in the method of preparing the compound of formula (I) according to the present invention. In formula (JI), X and R1 preferably, or in particular have, the above-mentioned relevant description of the compound of formula (I), or particularly preferred definitions of X and R1. The compound of formula (I) is known and described in Japanese Patent Publication No. Sho 56-45452 and the like. Examples which may be mentioned are: 4-fluoro-4'-methylsulfonyloxybenzophenone hydrazone, 4-fluoromethylsulfonyloxybenzophenone hydrazone, 4-fluoro-4'-trifluoromethanesulfonyloxy Benzophenonehydrazone and 4-fluoro-4'-trifluoromethanesulfonyloxybenzophenonehydrazone. Formula (III) provides a general definition of the sulfamethazine compounds which are also used as starting materials in the method of preparing compounds of formula (I) according to the present invention. The size of this type of paper is applicable to the Chinese National Standard (CNS) A4 specification (210X 297mm). Button-fixing-(please read the notes on the back first-this page), 〇〇5324 A7 Employee consumption of the Central Standards Bureau of the Ministry of Economic Affairs Cooperative Duprinting B7 V. In the description of the invention (6) (1Π), R2 and R3 are preferably, or in particular, have the above-mentioned relevant or particularly preferred R2 and R2 compounds in the description of the compound (I) Definition of β 3. Compounds of formula (ΠΙ) are known and described below, for example: 11〇1 ^ 611-Weyl, Methoden der organischen Chemie, Band XI / 2, page 693, 1958 and ibid., Band E XI, page 994, 1985, published by Georg Thieme Verlag. Examples that may be mentioned are: N-methyl sulfazone, N, N-dimethyl sulfazone, N-ethylamine sulfazone , N-propylamine sulfonamide, N-isopropylamine sulfonamide, N-butylamine sulfonamide, and N-methoxycarbonylmethylamine sulfonamide. The above preparation method (a ), Any suitable inert organic solvent can be used as the diluent. Examples of the above-mentioned diluent can be aliphatic hydrocarbons optionally Aromatic hydrocarbons and aromatic hydrocarbons, such as' pentane, hexane, cyclohexane, petroleum ether, petroleum petroleum, benzene, toluene, xylene, two-gas methyl embankment, gas imitation, four gasification carbon, 1,2- Difluoroethane, dichlorobenzene, difluorobenzene, etc .; ethers, such as diethyl ether, methyl ethyl ether, isopropyl ether, butyl ether, dioxane, dimethoxyethane (DEM), tetrahydrocarbon (THF), diglyme (DGM), etc .; ketones, such as acetone, methyl ethyl ketone (MEK), methyl isopropyl ketone, methyl isobutyl binding (please read the back first Please note that this page is not required to write this page.) This paper uses the Chinese National Standard Falcon (CNS) A4 specification (210X 297 mm). The Central Standards Bureau of the Ministry of Economy and Industry Cooperative Cooperative Printed A 7 B7_ V. Invention Instructions (7) Ketone ( MIBK), etc .; carbohydrates, such as ethyl ketone, propyl ketone, propylene carbolic acid, etc .; esters, such as ethyl acetate, ethyl acetate, etc .; amines, such as dimethyl methyl amide (DMF), dimethyl Acetamide (DMA), N-methyl sigmapyrrolidone, 1,3-dimethyl-2-imidazolidinone, hexamethylphosphoric triamine (HMPA), etc .; Classes, such as dimethyl sulfoxide (DMSO), ring wind, etc. The method according to the invention can be carried out in the presence of a base, and examples of the above mentioned tests that can be mentioned are inorganic tests, such as metal hydroxides, carbonates and bicarbonates, such as sodium bicarbonate, potassium bicarbonate, sodium carbonate , Potassium carbonate, lithium hydroxide, sodium hydroxide, potassium hydroxide or calcium hydroxide, the organic bases that can be mentioned are alcoholates, tertiary amines, dialkyl anilines and 0 bites such as methanol sodium, Third butanol_, triethylamine, 1,1,4,4-tetramethylethylenediamine (TMEDA), N, N-dimethylaniline, N, Ν-diethylaniline, pyridine, 4 -Dimethylaminobispyridine (DMAP), 1,4-diazabicyclo [2.2.2] Sinvale (0 children 8 (: 0) and 1,8-diazabicyclo [5.4.0] Undec-7-ene (DBU) and so on. When carrying out the method according to the invention, the reaction temperature can be varied within a relatively wide range. Generally, the method is carried out between about 0.0 to about 120 · ', preferably between about 20 · 〇 to about 80¾. The reaction preferably takes place under normal pressure, but it can also be carried out under increased or reduced pressure. When performing the preparation method (a), in the presence of diethylamine, in the presence of diethylamine, the compound of formula (Π) and the compound of formula (shellfish), for example, the compound of formula (Liao) with 1 mole By reacting with the ratio of Wu (1Π) compound of 1.2 mo! E, the desired compound can be obtained. The plant has a good tolerance to the active compound. The active compound is on the paper scale applicable to the Chinese National Standard (CNS) A4 specification (210 / 297mm -------- clothing -------- 1T ------ # (Please read the precautions on page f / write this page first) A7 B7 305S24 V. Description of the invention (see Zhengnian Λ YY 7) It is beneficial to add toxicity to warm-blooded animals Within the level, and can be used to control arthropod pests, especially in agriculture, forestry, protection of storage and materials, and insects encountered in the field of sanitation. Normally sensitive and resistant strains of this active compound to pests, and Pests are active during the entire developmental stage or individual developmental stages. The above-mentioned pests include: Isopods, for example, Tidal bugs, stags and sorrels (Porcellio scaber). Suborders, for example, with zebra land. Lips For example, for example, Geophilus carpophagus and Ting. For example, for example, for example, Integrated Reticulata, Lepidoptera, Lepidoptera, Orthoptera, Blattidae, Cricket, Lepidoptera, for example, Isoptera, for example, garden sleeves. Western fish. Insect (Onychiurus armatus). Oriental cockroach, American cockroach, Madeira cockroach, German mole cricket, tropical migratory locust, long-headed locust and grasshopper. European bulbous scorpion. Termite. Termite. Printed by the Consumer Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs System --------- ^-(Please read the precautions on the back before filling in this page) Lice, for example, Grape nodule aphid, cotton aphid, head lice, blind lice and jaws. Erythropomorphus, for example, plume and squirrel. Thysanoptera, for example, Greenhouse thrips and Tobacco thrips. Heteroptera, for example, Corydalis, cotton-red cricket, beetle, beetle , Rhodnius prolixus and bloodsucking genus. 10-This paper scale is suitable for China National Standard Falcon (CNS) Λ4 specification (210X297 mm) A7 — _ ----- ^ _ _ B7 5. Invention Description (

Employee Consumer Cooperative of Central Bureau of Standards of the Ministry of Economic Affairs printed 12 Homoptera, for example, cabbage cabbage whitefly, cotton whitefly, green housefly whitefly, cotton worm tooth, cabbage aphid, green tea aphid, sugar beet aphid, apple aphid, apple cotton Transgenic Peach Aphid, Aphis gossypii, Myzus spp., Myxophyllum sphaeroides, Aphis gossypii, Psylla spp , Nilaparvata lugens, red round scale scales, ivy round scale scale scales, mealybug genus and psyllium genus. Lepidoptera, for example, red beetle's pine inchworm, winter worm moth, fine moth, nest moth, small series, caterpillar caterpillar, yellow poison moth (Euproctis ^ ehfyS〇fi * h〇ea), genus Moth, cotton leaf Moths, Orange leaf moths, Diplodocus, Rhizobia, Brown armyworm, Egyptian cobalt codonopsis, Cotton worm, Chlamydomonas, Brassica spp, Spodoptera litura, Spodoptera litura, Spodoptera , Cabbage moth, Codling moth, Corydalis, Diplodia, Corn borer, Mediterranean meal =, wax moth, bag moth, net moth, brown leaf moth, leaf moth (CaCM, podana) , Cigarette moth, spruce leaf moth, grape fruit codling moth, tea long a moth and oak leaf curl. I Coleoptera, such as' furniture codlings, codlings, soybean elephants, bean elephants (Bruchidius obtectus), Cerambycidae, blue-hair hipped beetle beetle, yam beetle beetle, horseradish beetle beetle, leaf beetle, Brassica napus, Mexican bean ladybug, Atomaria spp., Sawgrass, flower weevil, valley weevil, grape black-eared beak weevil, cabbage weevil, alfalfa leaf weevil, Nephrolepis spp., Dermestris, Black Dermestris, Round Dermestris, Black Fur Dermestris, Mesothelius, Rapeseed Pteris, Arachnids, Golden Arachnid, Wheat Arachnid, Pseudospermum , Yellow powder beetle, beetle genus, genus Needles, beetle, June beetle and costely zealandica. Hymenoptera, for example, pine bees, wasps, ants, kitchen ants, and wasps

-1-! (Please read the precautions on the back before filling this page J, 1T- This paper size is applicable to China National Standard Falcon (CNS) A4 specification (210X 297mm) A7

A7 Pingyue Η Η i8 & 7 · i A χ, description of invention (genus 0 Diptera, for example, Aedes, Anopheles, Culex pipiens, Drosophila melanogaster, Musca, Musca Red-headed fly, green fly, gold fly, gangrene, gastrin, hyppobosca spp., Sting snail, nasal bump, dermatogium, gadfly, tania (Tannia spp.), Caterpillar mosquito (bibio hortulanus), Swedish wheat stalk, snail, beet leaf weed, Mediterranean fruit fly, olive fruit fly and European mosquito. The active compounds can be converted into conventional formulations , Such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powder residues, granules, concentrated suspensions / emulsions, natural and synthetic materials impregnated with active compounds , Microcapsules and seed coating composition in polymers, the active compound can also be converted into preparations for combustion equipment such as fumigation cylinders, fumigation tanks, fumigation rings, etc., as well as ultra-low volume cold mist preparations and hot mist preparations These preparations are produced by known methods, for example by combining active It is prepared by mixing the filler with a filler, that is, a liquid solvent and / or a solid carrier, optionally using a surfactant, that is, an emulsifier and / or a foam-generating agent. In the case of using water as a filler, for example, an organic solvent can be used It is used as auxiliary solvent. The suitable liquid solvents here mainly include: aromatic compounds, such as xylene, toluene or emulsyl, gasified aromatic compounds or gasified aliphatic hydrocarbons, such as gaseous benzene, gaseous ethylene Or two gas methane, aliphatic hydrocarbons, such as cyclohexane or Hyundai smoke, for example, treatment oil balance, treatment oils and vegetable oils, alcohols, such as butanol or glycol and their ethers and vinegars, ketones Types, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strong polar solvents, such as dimethyl methyl ketamine 12 This paper size is applicable to China National Falcon (CNS> Λ 4 specifications (210X297 () Please read the precautions on the back before filling in this page) Ordered by the Ministry of Economic Affairs Central Consortium Bureau Employee Consumer Cooperative Printed by the Ministry of Economic Affairs Central Standards Agency Employee Consumer Cooperative Printed A7 B7 V. Description of Invention (u) and dimethyl Sub-tropical wind and water; so-called liquefied gas filling Or carrier refers to a liquid that is a gas at room temperature and atmospheric pressure, such as aerosol propellants, such as halogenated hydrocarbons and Ding, Bing, nitrogen and carbon dioxide; suitable solid carriers here are: for example ammonium salts and natural Mineral powders, such as kaolin clays, Xinzhan clays, talc, baiyao, quartz, anemite, montmorillonite or diatomite, and synthetic mineral powders, such as highly dispersed silica, alumina and silicate; Solid carriers suitable for granules are: for example, crushed and graded natural rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as inorganic particles and organic powder, and organic particles such as sawdust, coconut husks, and ears of corn Cores and tobacco stems; suitable emulsifiers and / or foam-generating agents here are: for example, nonionic and anionic emulsifiers, such as polyoxyethylene fatty acids, oxyethylene fatty alcohol ethers, such as aryl aryl Jizhong glycol ether, alkylsulfonate, alkyl sulfate, arylsulfonate and protein hydrolysate; suitable dispersants here are: for example lignin monosulfite waste liquor and methyl fiber Prime. Binders such as carboxymethyl cellulose and natural and synthetic polymers in the form of powder, granules or latex, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids such as cephalin and lecithin , And synthetic phospholipids, can also be used in formulations. The additives can be mineral oil and vegetable oil. Colorants such as inorganic pigments such as iron oxide, titanium dioxide and Prussian blue, and organic dyes such as alizarin dyes, azo dyes and metal cyanine dyes, and trace nutrients such as iron, manganese, butterfly, copper, and The zinc and zinc salt formulations usually contain 0.1-95¾ (weight) of active compound, preferably this paper size is applicable to the Chinese National Standard (CNS) A4 specification (210X297 mm) --------- ¾ clothing- ----- ΪΤ ------ ^ (Please read the notes on the back first. Fis fill in this page) * A7 V. Description of the invention () Year shoulder g hey soil _ Both 7: v 補 玄. 0.5- 90¾ 〇 The active compound according to the present invention can be present in its market as a mixture with other active compounds such as insecticides, attractants, disinfectants, acaricides, nematicides, fungicides, growth regulators or herbicides In the preparations sold and in the use forms prepared from the preparations. For example, insecticides include: phosphate esters, carbamates, carboxylic acid esters, halogenated hydrocarbons, phenylureas, substances produced from microorganisms, and the like. The following compounds may be mentioned: flufluthrin, cypermethrin, flufluthrin, flufluthrin, brofenprox, cis-permethrin, clarith Clocythrin, cypermethrin, cypermethrin, cyhalothrin, cypermethrin, deltamethrin, fenvalerate, dimethrin, trimethrin, Fenvalerate, fluvalinate, fluvalinate, cypermethrin, pyrethrin, pyrethrin, pyrethrum, silafluofen, sixi Printed by Zetamethrin, Zetamethrin, Employee Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs (please read the precautions on the back and then fill out this page). Granville, Ding Youwei, Ceviin, Trimethoprim, Benzocarb, Fenobucarb, Dioxycarb, Isocarb, Methacarb, Methacarb, metolcarb, A Youbalavir, anti-aphid, rapamyl, cannibald, tertylcarbacarb, thiodiazepam, tecarbacarb, trimethacarb, dimethacarb, xylylcarb, this paper size is applicable China National Standard Rate (CNS) A4 specification (210X297 public financing) A7 B7_ printed by the employee consumer cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs V. Description of invention () Year and month B amendment list 7. 16 supplementation of methamidophos, ethyl valley Thiophos, azinphos-methyl, bromothion-A, thiophos-triphosfos, chlorpyrifos, phoxim, chlorpyrifos, chlorpyrifos-methyl, fenaconitrile, methyl endophosphorus, thiophosphorus Isomer, endophosphorus-sulfur chamoisomer, diazinon, dichlorvos, diliphos (die liphos), dephosphorvate, phoxim, dimethoate, methyl toxin, dichlorvos Phosphorus, B-mixed phosphorus, Kefensan, Ethion, and gas. Pyridoxine, Fenpyr, Fenthion, Dibenthion, Anguo, Gypion, Iprobenfos, Isoxazolium, Isoxafos, Methaphos, Malathion, Aphiphos, mervinphos, methionine, cochlear worm, methylamine scales, dibromide, omethoate, hypo-absorption, oxydeprofos, parasulfonium , Methyl parathion, rice Fengsan, methamidophos, fenthion, phoxim, phosphoramid, phoxim, ethyl fenpyr, fenpyr, fenpyr, fenthion, Faguo, pyrazophos, pyridazin, 4 thiophene, trimethoprim, hexametholone, moth phosphorus, eprofen, carbendazim, dithiophos, methyl ethyl phosphorus, thiophene Phosphorus, trichlorfon, triazophos, aphidone, meazizinone, chlordiazepoxide, flucarbazone, flubenzuron, flufenuron, fluflubenzuron, tebufenozide, tebufenozide Chrysanthemum, triflumuron (triflumuron), imidacloprid, nitenpyran (nitenpyran), N-[(6_ 气 -3-〇ΛByte) -methyl] -Ν'-cyano-Ν -Methylacetoimide-amidoamide (ΝΙ-25), qisolin, wormamidine, alme Uvermectin), Aziz Della -It a paper scale applicable to Chinese National Standard (CNS) Α4 Specification (210Χ 297 public Lu) (Please read the notes on the back of this page and then fill in) -β 4¾ 4¾

r ..................... R〇cfatCT «4SL25 ftr aded Paget Today 1¾ Book il-fif First Thought and Benefit ^ S ^ Hica \ ion-Encl. — f Min swollen 85 ^ Ϊ2Β2β '; ^ # child g, (Amended k Subnitted on Decenber j2 ^, 1996) 5. Description of the invention () Ding (azadirachtin), insecticidal sulphur, Bacillus thuringiensis, fenfluramine, snail killing , Emamectin, vinegar cool, fenpyrad, fenpyrad, fipronil, flufenprox, lufenuron, paraformaldehyde, mibenac Mi lbemectin, pymetrozine, tebufenpyrad, triazuron, aldicarb, oxacarb, procarbacarb, furandan, butylsulfoxide Kebai, chlorethoxyfos (chlorethoxyfos), Xieweiwei, Yixiongwei, Yishoubao, Qi. Pyridinium scales, gram scales, fiproni, fipronil, pyrazosin, carbendazim, hexaflux, isoxafos, isopropylamine, diflubenzuron, long-acting scales, Nitenpyram (nitenpyram), methamphetamine, methamidophos, phoxim monument, prothiopine (01 " 〇1: 11 丨 (^ 〇5), Vilafluoromethod 〇71-3 (: 111 ( ^ 〇5), sebufos (sebufos), silafluofen (silafluofen), tebupirnn (tebupirnnphos) 'sflufluthrin, terbutafos, thiodimethadol, thiafenox ), 'Cyclothione, pyridaben, tetrabenzine, tricyclotin, difenthiurom, dithiothiuram, ethionine, emaraectin, 4 snails, selenium tin, fenthiocarb, Fenprolpatrin, fenpyrad, fenpyramide, fluazinam, fluazuron, flufenuron, fipronil, fluvalinate , Fufenfen (fubfenprox), snail ketone, imetem (i vemect: in), chlordiazepoxide, yasuling (一 f. -........ .. this paper China National Standard 7 ^ — 44 specifications (210χ 297 public sounds) ------ a binding} yA, (please read the back first Please refer to this page for more details) Printed by the Employee Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs

Mm Ministry of Economic Affairs Central Standards Bureau Employee Consumer Cooperative printed monocrotophos), moxidectin (moxidectin) 'dibromophos, phosfos, bromopropyl, pyraclofos, shouting 6 tongs, Rimfen ( pyrimidifen), tebufenpyrad, thuringiensin, triarathene, and 4-bromo-2- (4-gasphenyl) -bu (ethoxymethyl) -5- (tri Fluoromethyl) -lBh pyrrole-3-carbonitrile (AC303630). . The active compounds according to the present invention can also be present as mixtures with synergists in their commercially available formulations and use forms prepared from these formulations. ◊ Synergists are compounds that can increase the effect of active compounds. The synergist itself need not be active. The content of active compound in the use forms prepared from commercially available preparations can vary within wide limits. The concentration of the active compound in the use form may be from 100 to 100% by weight of the active compound, preferably from 0001 to 1% by weight. The compound can be used in a conventional manner suitable for the use form. When used to control sanitary pests and pests in quarries, this active compound has an excellent residual effect on wood and clay, and has good stability against alkali in lime substrates. The following examples illustrate the present invention more specifically. However, it should be understood that the present invention is by no means limited to these embodiments. -丨 Yiliang paper size is suitable for Guanjia County (CNS) M specifications (2 丨 ⑽ plus company director — ^ ------ 1T ------. 4. (Please read the notes on the back first Guang, A page) · 305824 A7 V. Description of the invention (year, month, day, synthesis example 1

4-Fluoro-4 · -methanesulfonyloxybenzophenonehydrazone (3.08g) and triethylamine (1.20g) were dissolved in dimethane (U〇ml), and N- was added dropwise under ice cooling A solution of methanesulfonate gas (1.30g) in methane (5m 丨). Subsequently, it was stirred at room temperature for 16 hours. After the reaction was completed, the product was washed with dilute hydrochloric acid and water and dried over anhydrous magnesium sulfate. After distilling off the solvent, the product was purified by silica gel column chromatography (n-hexane: ethyl acetate = 4: 1) to obtain the desired product N- (4-fluoroW-methylsulfonyloxydiphenylmethylimine Radical) —N′-methylsulfonamide (2.80 g), which is a mixture of isomers (cis-isomer / trans-isomer = approximately 1: 1). Melting point: 50-56 * C. Synthesis Example 2 ch3

Printed by the Staff Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs (please read the precautions on the back before filling in this page). Combine 4-gas-4 · -methylsulfonyloxybenzophenone hydrazone (3.25g) and 4-N, N -. This paper scale is applicable to Chinese National Standard (CNS) Α4 specifications (2 丨 0X29? Mm) A7 B7 5. Description of invention (16) Methylaminopyridine (1.46g) is dissolved in toluene (30ml), Under ice-cooling, a solution of N, N-dimethylsulfamide (1.72 g) in toluene (5 ml) was added dropwise. Subsequently, the heating and refluxing was carried out for 4 hours. After the reaction is completed, it is treated in a manner similar to Synthesis Example 1 to obtain N- (4-gas-4'-methylsulfonyloxydiphenylmethylimino) _N \ fT-dimethylsulfonamide Amine (2.2 g) is a mixture of isomers (cis / trans = approximately 1: 1). Melting point: 55-60 ° C. 'Follow the following general preparation conditions in a similar manner to obtain the following compounds of formula (I): I nn ——— I- tmi mu In I nf ^ i ^^ — ^ 1 m ^^ tm mu (please read the back side first Please pay attention to fill in this page) 1. The paper standard printed by the Staff Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs is applicable to the Chinese National Standard (CNS) A4 specification (210 X 297 mm) 5. The description of the invention (17) Table 2

O 'R I M / NH—S—N

Α7 Β7

X

(DR 'Compound No. X Rl R2 R3 Melting point l ° C] Li_ F CHj H ch2ch3 65-70 4 Cl CH3 HH 142-145 5 α CHj H ch3 67-71 6 Cl CHj H ch2ch3 146 ^ 147 7 α CH , Λ H CHXHnCHj 131-133 8 Cl CH. I H CH (CH-), 76-82 9 Cl ch3 H CH, CH2CH2CH3 120-125 10 Cl CHj H CHrC02CH3 117-120 11 Cl ch3 H COrCH2CH3 56-61 12 Cl ch3 H C02-C (CH3) 3 '85-89 13 Cl cf5 H CH2CH3 n-87 j 3kf ht Ψ Yun' ί loaded Ding% Ministry of Economy China and South Korea A member X negative Μ% -19 This paper size is applicable to Chinese national standards (CNS) Α4 specification (210X297 company director) A7 B7 V. Description of the invention (18) Biological test examples Comparative compound C-1:

The Central Bureau of Standards of the Ministry of Economic Affairs for the industrial and consumer cooperation du printing (this compound is described in Japanese Patent Publication (Publication) No. 54-122261) using Spodoptera litura larvae to test the preparation of the test preparation solvent: 3 parts by weight of mixed xylene emulsifier: 1 part by weight of polyoxyethylene alkyl phenyl ether, in order to prepare a suitable formulation of active compound, 1 part by weight of active compound and the above given amount of emulsifier with the above given amount Solvent mixing. Dilute the mixture with water to the given concentration. Test method The cabbage leaves were immersed in an aqueous solution of a given compound with a given concentration, the solution was dried in air, and the cabbage leaves were placed in a petri dish with a diameter of 9 cm. Place 10 3-instar Spodoptera litura larvae in the Petri bacterial culture sub-unit, and place the Petri bacterial Petri dish in a room controlled at a strange temperature of 25t5. After 7 days, count the number of dead insects and calculate the percentage of death. The trials were conducted in two groups, and the percentage of deaths in each trial was given as an average value. The results are shown in Table 3. -20-The size of this paper is far from the Chinese National Standard (CNS) A4 (210X297mm) (please read the notes on the back to write this page)-binding line printed by the Ministry of Economy Central Standards Bureau Employee Consumer Cooperative A7 B7 V. Description of the invention (19) 4_3 Compound number concentration (ppm) Percentage of death 6 40 8 100 100 7 • 40 8 100 100 8 40 8 100 100 9 40 8 100 100 10 40 8 100 100 C-1 40 8 100 0 • -Binding line (please read the notes on the back for writing this page) This paper size is applicable to China National Standard (CNS) Α4 specification (210Χ 297mm)

> 1 ROC Patent Appln. No. 84105125 for the Arsenic Application No. 84105125 $ Amendment Page-Attachment ㈠ fled Pages of the Chinese Soecification-Fnri ii \ F is for 丨 b to submit)-~~ (Submitted oqJuly | G, 1996)

Du Printed by the Ministry of Economic Affairs Central Bureau of Accreditation and Employee Consumption Cooperation

Koichi Tateno (Koichi Tateno) Year Λ flavor J5J2U ^ 305824 ^ Patent specification Sulfadiamide derivatives, their preparation and their use in controlling pests

Sulfamide derivatives, a process for their preparation and their use for combating animal pests. 』· Yiichi Otsu 2Yoshinori Kitagawa YumiHattori 4Katsuaki wada Katsuaki wada Bayer NIHON BAYER AGROCHEM KK mi liters 10B, Japan Gutter 1 " Paper size Gujinguan ^^ (<: Called the grid (2 offer 297 mm " 7

Application Date] -------- Case No. ^ ^ (〇sr (category Γ 1 and above each block 4 are filled in by this Bureau) _ Application No. 84105125 ROC Patent Appln. Attachment ㈠; s of the Chinese Specification-Enc 1 (1) (presented by lb ak in July 8b) ~~ 1 (Submitted o'July \ L ·, 1996) ^ 305824 Ming Patent Specification Invention Name Chinese English Sulphur Acetamide derivatives, their preparation and their use for controlling pests

Sulfamide derivatives, a process for their preparation and their use for combating animal pests · Name Nationality Inventor's Residence and Residence Name (Name) Ministry of Economic Affairs Central Engagement Bureau Negative Work Consumer Cooperative Printed Nationality III, Applicant's Residence and Residence (Office ) Representative name Yuichi otsu (Yoshinori Kitagawa) < 3. 服 部 裕美 (yumi Hattori) 4. Kadaaki Wada «5. Toru Obinata (Toru Obinata) 丄 一 5. All Japanese books 2_ 7-7, Ekinancho, Oyaxna-shi, Dinan-cho, Oyama City, Yogi-gun, Yogi, prefecture, 2 · Aramachi, Moka-shi, Tochigi, Aimachi 851085, Aramachi, Moka City, Tochigi Prefecture, Japan , Japan _ _ 3 · Yuki, Yuki-shi, Ibaraki, Japan4, Yuki, Yuki-shi, Ibaraki, Japan4, Yuki, Yuki-shi, Ibaraki, Japan4, 7-11-20 7-11-20, Japan Jyoto, Oyama-shi, Tochigi, Japan 5. 1-9-31 1-9-31, Iwaki-cho, Oyama-shi, Kokubangi Prefecture, Japan 1-9-31, Wakagicho, Oyamachi, Tochigi, Japan, Tokyo, Japan 1. Huh, Takamori, Tokyo l〇8, Japan 10-8, Takanawa 4-chome, Mmato Ku, y Koichi Tateno (CNS) (210X297 / ^ *)

Tochigi, Japan binding line

Claims (1)

, ^^ 3 ^^ 84105125Annin. No.84105125 Jing Jingwei Chinese text-Annex II ~~~-£ lgigs in Chinese-Encl. (Il) in uainese-bncl. (L Formula (Ϊ) compound ( S—iA》 Country. 2nd present to W) ο η / NH ~ s — N " II \ R U) Printed by the Employees Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs where x stands for halogen, R1 stands for Ci-c4-alkyl or Ci-C4-i for alkyl, R2 stands for hydrogen or (: 〖-C4-alkyl, and R'3 represents hydrogen 'C 1 -C 4 -pit group, c 1 -c4 -oxygen-obtained group or ci c4 -alkyloxy group methyl group 2. Compounds of formula (I) according to item 1 of patent application , Which in turn represents fluorine 'gas or bromine, R1 represents Ci-Cr alkyl or C1-C2-substituted alkyl, R2 represents hydrogen or Ci-C2-alkyl and R3 represents hydrogen, 1-c4-alkyl, c 1 -c4 -alkyloxycarbonyl or c 1 C2 -alkyloxymethyl. 3. According to the compound of formula (I) in item 1 of the patent application, where X represents fluorine or gas, and R1 represents methyl or trifluoromethyl R2 stands for hydrogen, methyl or ethyl and R3 stands for hydrogen, methyl, ethyl, n-propyl, isopropyl, and n-butyl. The paper standard is applicable to China National Standard (CNS) A4 specification (210X297mm) ( Please read the precautions on the back before filling out this page) fcr 言 Γ 甲 Printed by the Employee Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs. 6. Applying for a patent application. Methoxy-amethyst 'ethoxyl-based, third-butoxy-based or methyl-based based. .According to the compound of formula 1 in the first patent application, where X represents fluorine or gas, R 1 represents methyl, R 2 represents hydrogen and RJ represents ethyl, n-propyl, isopropyl, butyl or methyl Oxyfluorylmethyl 5_-a method for preparing a compound of formula ([) according to item 1 of the scope of patent application, which is characterized in that the compound of formula (K) and the compound of formula () are carried out at a temperature between 〇.〇 and 120eC The reaction, if necessary in the presence of a base, and if necessary in the presence of an inert diluent, on where X and R1 have the definition as defined in item 1 of the scope of patent application where 0 II R CI — s —N '> \, 〇 R3 (110 and R3 have the definition as specified in item i of the scope of patent application. 23 This paper size is applicable to the Chinese National Standard Falcon (CNS) A4 specification (210X297 mm). IU2Lz2. U Patent scope 6.-A pest control composition, The special feature is that the composition contains at least one compound of formula (1) according to item 1 of the patent application scope. 7. A method for controlling pests, characterized in that the compound of formula (I) according to item 1 of the patent application scope Apply to pests and / or The environment in which it exists. (Please read the precautions on the back before filling in this page) Zhang Yi-'printed by the Beigong Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs -24 This paper scale is applicable to the Chinese National Standard (CNS) A4 specification (210X297 Mm)