TW200526611A - Nematicidal difluoroalkenes - Google Patents

Abstract

The invention relates to a compound of the formula (I), wherein R represents hydrogen, halogen, alkyl, cycloalkyl, alkoxyalkyl, alkylthioalkyl, haloalkyl, alkoxy, alkylthio, represents optionally substituted phenyl or benzyl, or represents optionally substituted heteroaryl containing at least one heteroatom selected from N, O and S, m represents 3, 4, 5, 6, 7, 8, 9 or 10, and n represents 0, 1 or 2, a process for preparing said compound, compositions comprising said compound and its use for combating pests.

Description

200526611 IX. Description of the invention: [Technical field to which the invention belongs] The present invention relates to difluoroene compounds, a method for preparing the same and its use for controlling pests. [Background of the Invention] WO 86/07590 discloses certain polyhaloalkene compounds having nematicidal activity; U.S. Patent No. 3,513,172 φ also discloses certain trifluorobutenyl compounds having nematicidal activity GB ίο 2 293 380 A discloses certain heterocyclic compounds having nematicidal activity; WO 95/04727 A1 describes a method for preparing fluoroalkenylthio heterocyclic derivatives; WO 95/24403 A1 is also described as being used as A method for preparing 4,4-difluorobutenyl compounds of nematicides; finally, WO 99 / 52874A1 discloses difluoroene derivatives that may be used as animal pests, but 15 these compounds have not been known to date. Get any special importance. [Summary] A novel difluoroene has been discovered, which can be represented by the following chemical formula:

200526611 k R represents hydrogen, halogen, alkyl, cycloalkyl, alkoxyalkyl, alkylsulfanyl, haloalkyl, alkoxy, alkylthio, and optionally substituted benzyl or benzyl Methyl, or represents a optionally substituted heteroaryl containing at least one heteroatom selected from N, 0, and "m" represents 3, 4, 5, 6, 7, 8, 9, or 10, and n represents 0, 1 or 2. The compound of formula ⑴ is extremely active against nematodes, and this type of formula also exhibits excellent insecticidal and herbicidal activity. In the meaning, hydrocarbon chains, such as alkyl, η, The suitable substituents or branches listed in the above formula # will be described later. The range of the above-mentioned compounds of the formula (I) can be synthesized, for example, the preparation method (a) of # and the following The above-mentioned production method (b) is obtained by the following production method (a) This novel substituted difluoroene compound of the formula (1) is prepared by: letting the compound of the formula (II), where η is 0.

Where R is as defined above and reacts with a compound of formula (III) 200526611 M-S02-0- (CH2) mCH = CF2 (III) where 5 M represents methyl or p-fluorenyl, and m is as defined above . Production method (b) This novel substituted difluoro compound of formula (I), wherein η is 110 or 2 is prepared by: oxidizing the compound of formula (la) with a suitable oxidant

R

° S— (CH2) mCH = CF2 (la) 15 where 11 and 111 are as defined above. In the present specification, "halogen" 'preferably represents fluorine, gas, bromine or iodine, and particularly preferably gas' or gas.

"Alkyl" preferably represents a straight or branched Cm2-alkyl group, such as methyl, ethyl, n- or isopropyl, n-, iso-, second- or third-butyl, n-pentyl Group, 20 n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-H alkyl, n-dodecyl, etc., and especially fluorenyl, ethyl , N- or isopropyl 'n-, iso-, second- or second-butyl' n-fluorenyl or n- " hexyl. "Cycloalkyl" preferably represents C3_8-cycloalkyl, particularly suitably cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, or cyclooctyl, and preferably 200526611 'cyclobutyl, Cyclopentyl or cyclohexyl. The definition of alkynyl is also applicable to ", alkoxyalkynyl", "thiosulfanyl", and self-fractionation.

In order to represent cyclopropyl, cyclobutanyl is preferably a heterocyclic group having 5- or 6-membered heterocyclic groups, and at least one in the ring, preferably 1-3. From heteroatoms of N, 0 and s, a more preferred heterocyclyl group represents a group selected from the group consisting of sulfanyl, σ-sedynyl, ° -ratio σ-fixed, sputtered-branched and tritium-based groups. Preferred compounds of the formula (I) according to the present invention, wherein 10 R represents hydrogen, chlorine, fluorine, bromine, Cu-alkyl, C3-8-cycloalkyl, c2-6 (total number of carbon atoms)-alkoxyalkyl, C26 (total number of carbon atoms alkylsulfanyl, substituted by chlorine_ or fluorine · (4-4-alkyl, Cu-xyloxy, alkylthio) represents a selective business element, Cm · xyl- 'Ciw alkoxy-, C ^ -thiothio-, Cm-halothio- or end group-substituted benzyl or benzyl 15 group, or representatively selected via halo_, Cm-alkyl-' Alkoxy- or Cm-dentylalkyl-substituted 5- or 6-membered heteroaryl groups having at least one hetero atom selected from ", 0 and S, m represents 3,4,5,6,7 , 8, 9, or 10 'and η represents 0, 1 or 2. 20 Particularly preferred compounds of formula (I) according to the present invention, wherein R represents hydrogen, chlorine, IL, molybdenum, Cw group, Cw-ring Carbyl, c2_4 (total number of carbon atoms) _alkenyloxy, C ^ 4 (total number of broken atoms) -alkenylsulfanyl, chlorine or fluorine-substituted Cw alkyl, Cu-hexyloxy , Cw alkylthio, which is optionally substituted with chloro-, fluoro-, bromo-, methyl-, methoxy-, 200526611 sulfanyl, trifluorofluorenyl- or nitro- Phenyl or benzyl, or bromo- or methyl-substituted succinyl, methylphenyl, tonyl, carnofluorenyl or oxoyl, m represents 3,4,5,6 , 7 or 8, and 5 η represents 0, 1 or 2. According to the reaction in the production method (a) of the present invention, for example, < & As a starting material, fluorenyloxy-6,6-difluoro-5_hexamidine can be described by the following reaction chart formula: ° 1〇jj, + H3C — S〇2 —O— (CH2) 4CH = CF2

S, SH N, s ^ \ / 3 According to the reaction in the production method (b) of the present invention, for example, 5 (66 15 difluoro-5-hexylthio) -1,2,4-thiadiazole and m -Chlorobenzoic acid, (oxidant μ is the starting material, which can be illustrated by the following reaction chart:

(CH2) 4CH = CF2 oxidation reaction / (CH2) 4CH = CF2

The compound of formula (II), which is used as the starting material in the above production method (a), is a compound that is mainly known in the following documents, for example, JP 01308270 A, WO 86/07590 A1, and WO 95 / 24403 A1, this compound of formula (II) can be easily obtained by known methods, for example, DE 4239727 -9-20 2026626611 A JP 60255782 A, JP 01308270 A, EP 0 534 219 A Eq. (II) A clear example of the compound is: 5-nitrothio-1,2,4-σ cydia α '5 5-hydrothio-3-amidino-1,2,4-thiadiazole, 5-nitro Thio-3-Second-butyl-1,2,4-fluorenediazyl '5-hydrothio-3-methoxy-1,2,4-thiadiazole, 5-hydrothio-3 -Phenyl-1,2,4-thiadiazole, 3 -ethyl-5-muranyl-1,2,4-fluorenyldifluorene 'ίο 5_muranyl-3-n-propylfluorene Sat '3-isopropyl-5-muranyl-1,2,4-σ-sedazid' '5-Azathio-3-n-butyl-1,2,4-sacridine' 5-Azathio-3-second-butyl-1,2,4-fluorenediσ sitting '5 -muranyl-3 -n-fluorenyl-1,2,4-dithiopyridine' 15 3 Propyl-5_nitrothio-1,2,4-σ cylidene '3-cyclofluorenyl-5-muranyl-1,2,4-fluorenediazyl' 3- ¾hexyl-5- Thio-1,2,4-11 cydiamidin '5-hydrothio-3-methoxyfluorenyl-1,2,4-thiadiazole, 3-ethoxyfluorenyl-5-nitro Thio-1,2,4- ° Serdijun '2〇3-isopropoxy-5 · Merthio-1,2,4-Dioxanyl' 5-Hydroxythio-3-methyl Thiothio-1,2,4-thiadiazole, 3-ethylthiothio-5-aminothio-1,2,4-π-cydiamidin '3-isopropylthiothio-5 -Rhamthio-1,2,4-σ cydiasigma 5 3 · chlorofluorenyl-5-hydrothio-1,2,4-thiadiazole, 200526611 3- (2-chloroethyl)- 5-Rhamthio-1,2,4-11 cydia: 1'-trifluoromethyl-5-hydrothio-1,2,4 · thiadiazole, 5-nitrothio-3 -Pentaethylethyl-1,2,4-fluorenediσ, 3 -ethoxy-5-rhamthionyl_1 acetodifluoride '5 3-isopropoxy-5-nitrothio-1 , 2,4-Cyclothiopyridine '5-azathio-3-amidosulfanyl-1,2,4-σxylopyridine Lyzed' 3-ethylsulfan-5-murinethio-1,2 , 4-Pyrosyl'sialo '3-isopropylthio-5-muranyl-1,2,4-pyridine's bis' 3-phenylfluorenyl-5-murthio-1,2,4-σ二 二 σ 坐 ′ ίο 3- (4-Gaphenylidene) -5 · rhamthionyl-1,2,4 · σ Base-1,2,4-11 plug two 17 sitting '3_ (4- > styrenyl) -5- Rhamthio-1,2,4-σ cydiabenzyl '5-azathio-3- (3-difluoromethylbenzyl) 1,2,4-17 cydiazyl' 5- Aminothio-3- (4-difluorofluorenylbenzyl) -1,2,4-fluorenedi. R'15 5-Hydroxythio-3- (4-methylphenylfluorenyl) -1,2,4-thiadiazole, 5-nitrothio-3- (4-methoxyphenylfluorenyl)- 1,2,4-fluorenedi °° '5-hydrothio-3- (4-fluorenylthiophenylfluorenyl) -1,2,4-thiadiazole, 3- (2,4 · dichlorobenzene Fluorenyl) -5-hydrothio-1,2,4-thiadiazole, 3- (2,4-diamidinophenylfluorenyl) -5-hydrothio-1,2,4-thiadiazole , 20 3- (2_fluorophenyl) _5_hydrothio-1,2,4-thiadiazole, 3- (3-fluorophenyl) -5_hydrothio-1,2,4-thio Diazole, 3- (4-fluorophenyl) -5-hydrosulfanyl-1,2,4-thiadiazole, 3- (2-chlorophenyl) -5-hydrosulfanyl-1,2,4 -Thiadiazole, 3-(3-chlorophenyl) -5 -nitrosyl-1,2,4-fluoranthionyl '200526611 3- (4-chlorophenyl) -5-nitrosyl-1, 2,4-11 cydiaxal '3- (4- > styrophenyl) -5-nitrothio-1,2,4-σ cydiaxine, 5 -nitrothio-3- (4- Diazinonylphenyl) -1,2,4-Hydroxydisyl '5-hydrothio-3- (3-fluorenylphenyl) -1,2,4-thiadiazole, 5 5-hydrosulfide -3- (4-Toluenyl) -1,2,4-thiadiazole, 5-hydrothio-3- (4-methoxyphenyl) -1,2,4-thiadiazole, 5 -Hydrothio-3- (4-methylthiophenyl) -1,2,4-thiadiazole, 3- (2,4-dichlorophenyl) -5-nitrothio-1,2, 4-σ plug two alpha sitting ' 3- (2,4-dimethylphenyl) -5-hydrothio-1,2,4-thiadiazole, 10 3- > odor-5-muranyl-1,2,4-σ Cydiazine '3- (2- ° Furanyl) -5 -nitrosulfanyl-1,2,4-11 Cysteine, 5-hydrothio-3- (2-thienyl) · 1, 2,4-thiadiazole, 5-hydrothio-3- (3-thienyl) -1,2,4-thiadiazole, 3- (5- > stilbene-2-yl) -5 -Nitrothio-1,2,4-17 cydia 17 ''15 5-nitrothio-3- (5-fluorenyl thiophen-2-yl) -1,2,4- cydia σ R ' 3- (4,5-Di > styren-2-yl) -5-nitrosulfanyl1,2,4-fluorene Base) -1,2,4-fluorenyldifluorene '5-windylthio-3- (3-11 to 11 amidyl) -1,2,4-11 -(4-pyridyl) _1,2,4-thiadiazole, 205-muranyl-3- (6-fluorenylsigma sigma-2-yl) -1,2,4-fluorenyldi-0 Sit, 3- (4,6-diamidyl_0 than biten-2-yl) -5-rathidin-1,2,4-σSeddi 11 sit, 5-ratthio-3- (2 -1? Dense bite) 1,2,4-11 plug two 11 sitting '5-nitrogenthio-3-(4-out σ fixed base) 1,2,4-π plug two σ sitting' 5- Murine thio-3-(2-π ratio π well-based) 1,2,4-σ plug two σ sitting. 200526611 Formula (in): A clear example of a compound is disclosed in

Known compounds in JP 11349557 A. Specific examples of the formula (III) are, for example: · 1-methanesulfonyloxy-5,5-difluoropentazone, 1-methanesulfonyloxy-6,6-difluoro-5-hexanone, 1 -Methanesulfonyloxy-7,7-difluoro-6-heptane, 1-fluorenylsulfonyloxy-8,8-difluoro-7-octylgui, 1-fluorenylsulfonyloxy-9,9 -Difluoro_8_nonyl, 1-mesitoxanthenyl_1, 10_difluoro_9_decife, _ 10 15 20 1-pyridylsulfonyloxy-11,11-difluoro 10-deca-ene, 1-methacryloxy 12, 12, difluoroheptadecene, and the like. Or, it is used as a starting material in the above-mentioned production method 疋 Aida Yuba in the formula (1) where η is 0, which is prepared similarly to the above-mentioned production method (&). According to the equivalent of Lt: system 3): =] for the oxidation formula (the suitable compound of hydrazone, it is commonly used in organic chemistry, such as peroxide lice solution, m-chloroperbenzoic acid, peracetic acid, Quickly review the unloading of magnesium diacid or peroxymonosulfuric acid. The reaction of peroxic acid, which is earlier than peroxygen, can be carried out in the presence of appropriate, suitable :: thin: Qi Guang For example, aliphatic, Cycloaliphatic and aromatic hydrocarbons, 笑, cage # 疋, mounting hexane, petroleum ether 'petroleum spirit, benzene, xylene, dimethyldibutyl ether, such as' diethyl ether' methyl ethyl ether 'Di · isopropyl ether, [j' di gauge, tetrahydrofuran, etc .; _, for example, propionate, methylethyl_ 'methyl isobutyl, etc .; nitriles, for example, -13- k 200526611 Propionitrile 'acrylonitrile' and the like; acid amines, for example, dimethylformamide, dimethylacetamide, N-methyl ^ bilodolone, etc. This reaction can be Performed in the presence of an acid binder. Suitable acid binders are, for example, hydroxides, carbonates and alcoholates of metals, 5 and tertiary amines, such as triethylamine, diethyl Aniline Pyridine, 4-diamidinoaminopyridine '1,4-diazabicyclo [2,2,2] octane (DABC〇), 丨, diazabicyclo [5,4,0] 11 -7-ene (DBU), etc. When the production method (a) of the present invention is carried out, the reaction temperature can be carried out over a relatively wide temperature range, 'normally, it is between 0.00 and 18.0. At the temperature, ίο is preferably performed at a temperature between 20 ° C and 120 ° C. The production method (a) according to the present invention is usually performed under atmospheric pressure, however, it is also possible to perform the reaction under elevated or reduced pressure. It is usually carried out between 0.1 bar and 10 bar. ^ The compound of formula (I) of the present invention can be obtained from, for example, a compound of formula (III) from 1 to 12 Mohr 15 and 1 Mohr. The compound of formula (Π) is prepared by refluxing in the presence of a 0.9-M mole acid binding agent (such as potassium carbonate) in a diluent '(such as acetonitrile). ^ The reaction of the above-mentioned production method (b) can be carried out in an appropriate manner. Diluents are carried out in the presence of, for example, aliphatic, cycloaliphatic and aromatic = optionally chlorinated), for example, hexane, cyclohexane, petroleum ether, petroleum. Benzene, methylbenzyl, Methylbenzyl, digas toluene, chloroform, carbon tetrachloride ',' burned 'gas benzene', etc .; Lai, for example, diethyl trip, methyl ethyl, ^ isopropyl ether, dibutyl ether, di Dioxane, tetrahydrofuran, etc .; alcohols, ~, such as methanol, ethanol, propanol, isopropanol, butanol, ethylene glycol, etc. Example 200526611 "Ethyl acetate, pentyl acetate Vinegar, etc .; acid amines, such as monomethylformamide, dimethyl ethyl amine, succinimidine, etc .; carboxylic acids, such as formic acid, acetic acid, and the like. #When carrying out the production method (13) of the present invention, the reaction temperature can be carried out in a relatively wide temperature range of 5 degrees, usually, at a temperature between -20 ° C and 100 ° C, preferably between 01: at temperatures between 80 and 01. The production method (b) according to the present invention is usually carried out under atmospheric pressure, however, it is also possible to carry out the reaction under elevated or reduced pressure, usually between 0.1 bar and 10 bar. 10 When the preparation method (b) is carried out, the related compound of formula (I) of the present invention can be obtained from: for example, from 0.8-3 moles of m-chloroperacetic acid and Moore's compound of formula (1) in It can be obtained by reacting in a diluent (such as dichloromethane) at room temperature. The compound of the formula (I) of the present invention exhibits a strong nematode and herbicidal activity, and they also have insect control activity, so they can be effectively used. In terms of, for example, agriculture and forest fungi, as nematicides and herbicides, but also suitable as nematicides and / or antiparasitic agents in the field of animal health, in addition to crops, The compound of formula (I) of the present invention exhibits low phytotoxicity. In this specification, "harmful organisms" refers to animals and plants that are harmful to crops or animals, including harmful nematodes, insects, and weeds. 20 According to the present invention The compounds are particularly useful for controlling plant-destructing nematodes, such as, for example, root nodule nematodes 油 / 0 油 ζ · _ still larvae; for controlling plant-destructing insects, such as, for example, peach aphids, mustard beetles z / eariae) Caterpillars / rwg towels that feed on grains; and also suitable for controlling damage -15- 200526611 Plants TWrawycAws wrifcae 〇 Nematodes that parasitize plants include, for example, Pratylenchus spp ·), Radopholus similes, 1 line & {Ditylenchus dipsaci), Cilenchus nematode (Tylenchulus semipenetrans), Heterodera spp., Heterodera spp.), Rhizoctonia (Me / o / i / o magic; we spp ·), leaf bud nematodes spp ·), needle nematodes spp ·), sword nematode spp ·), residual root nematodes (rr / c / zoc ^ rws spp ·) and pine Wood thread bug < with < 2/7 / ^ / 烈 (^ 1 ^ 8 卩 卩. ) However, it is not limited to these categories. At a certain concentration or application rate, the compounds according to the invention can also be suitably used as herbicides. The compounds according to the invention can therefore be used to combat, for example, the following weeds: Dicotyledonous Grasses: Sinapis, Leipidium, Galium, Stellaria, Chenopodium, Urtica 'Senecio, Amaran1; hus, Portulaca, Xanthium, Ipomoea, Polygonum, Ambrosia, Cirsium, Sonchus , Solanium, Rorippa, Lamium, Veronica, Datura, Viola, Galeopsis, Poppy (Papaver), Centaurea, Galinsoga, Rotala, Lindemia, etc. Hybrids of the monocotyledonous genus: Echinochloa, Setaria, Panicum, Digitaria, Timleum 200526611, Poa, poa Festuca, Eleusine, Lolium, Bromus, Avena 'Cyperus, Sorghum, Agropyron , Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Agrostis, see wheat Alopecurus, Cynodon, etc. However, the use of the compound of the present invention is by no means limited to the above-mentioned plants and plants, and it is also applicable to other plants. The compound of the present invention can be used as a non-selective or selective herbicide depending on its application concentration of 10 Agent, and can be used before the withering stage and after germination. All plants and plant parts can be treated according to the present invention. The term “plants” in the specification refers to all plants and plant groups, such as wanted and unwanted wild plants or crop plants (including naturally occurring crop plants 15), crop plants can be obtained by traditional plant breeding and optimization methods or by biotechnology and recombinant methods or by a combination of these methods, including transgenic plants and including protected plant cultivars or unprotected plants Varieties protected by the breeder's rights; the so-called plant parts can be understood to mean all parts and plant organs on the ground and below the ground, such as hoe, leaves, 20 flowers and roots, examples that can be mentioned are Leaves, needles, stalks, stems, flowers, fruit bodies, fruits, seeds, roots, bulbs and underground stems, plant parts also include harvested materials, and growing and reproductive materials, such as cuttings, bulbs, Underground stalks, short stolons and especially seeds, these compounds can, for example, be used to coat seeds to protect them from harmful organisms. -17- 200526611 As already mentioned, it can be treated in accordance with the present invention,-the preferred specific real estate, wild species plants Ί plants and their parts or those derived from traditional species (such as hybrid M species, and their parts, Treated; planted in another preferred and physique) 10 15 20 class, fungicides, growth regulators or herbicides; fungicides such as phosphates, amino esters, carboxylates And chlorinated hydrocarbons, phenylureas, and especially those produced by microorganisms. In addition, the active compound of the present invention is also used as a mixture with a synergist. Such formulations and application types are particularly useful as commercial products. The synergist itself must be inactive, but it can enhance the effect of the active compound. force. The transgenic plants and plants obtained through genetic engineering: j :, = In accordance with traditional methods (genetically modified organisms), and the definition of 2: suitable j or "plant parts" or: plant parts has been said earlier, / The active compounds according to the present invention may exist in the formulations and the types of formulations they can be prepared, prepared from these formulations, used as a mixture with other active compounds, other active compounds such as insecticides, toxic attractants The content of the active compound of the present invention in useful commercially available formulation swords or application types can be varied within a wide range, from commercially available formulations. The content of the active compound used in the preparation pattern can be varied over a wide range. The concentration of the active compound in the use pattern can be from 0.000 W to the active compound by weight, preferably between 0. Between 0001 and 1% by weight, the rate of application can also be varied over a wide range, and it is appropriate to use about -18-200526611 0 per hectare. An amount of 0.05 to 4 kg is more preferably used in an amount of about 0 to 2 kg of the active compound. Suitable components to be mixed are, for example, the following: 5 Fungicides: aldimorph, ampropylfos, ampropylfos-potassium, ammonium Andoprim, anilazine, azaconazole, azoxystrobin, benalaxyl, benodanil, exempt from 10 Benomyl, benmacril, benmacril_isobutyl, bialaphos, binapacryl, biphenyl, bitertanol ), Baomycin-S, bromuconazole, bupirimate, buthiobate, polysulfide, capsimycin, captafol, Captan, carbendazim, carboxin, carvon, quinomethionate, chlobenthiazone, chlorfenazole, Chloroneb, chloropicrin, chlorothalonil, chloline lozolinate), clozylacon, cufraneb, cymoxanil, cyproconazole, cyprodinil, cyprofuram ), Debacarb, dichlorophen, dichlorobutrazole, dichlofluanid, diclomezine, dicloran, dithiophene Diethofencarb, -19- 200526611 difenoconazole, dimethirimol, dimethomorph, diniconazole, deniconazole-M, dinocap ) 'Diphenylamine, dipyrithione, ditalimfos' dithianon, dodemorph, dodine, drazoxolon, Edifenphos, epoxiconazole, etaconazole, ethirimol, etridiazole, famoxadon, fenapanil ), Fenarimol, fenbuconazole, fenfuram ), Fenitropan, 10 fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin argon oxide ( fentin hydroxide), ferbam, ferimzone, fluazinam, flumetover, fluoromide, fluquinconazole, voltamin 1515 (flurprimidol) 'flusilazole, flusulfamide, flutolanil, flutriafol, folpet, fosetyl -Al), fosetyl-sodium, fthalide, fuberidazole, furalaxyl, furametpyr, furcarbonil ), Furconazole, furconazole-cis, furmecyclox, guazatine, hexachlorobenzene, hexaconazole, febenin (hymexazol) 'imazalil, imibenconazole, iminoc tadine), iminoctadine albesilate-20- 200526611 (iminoctadine albesilate), iminoctadine acetate, iodocarb, ipconazole , Iprodone (IBP), iprodione, irumamycin, isoprothiolane, isovaledione, kasugamycin, g Kresoxim_methyl, copper preparations, for example, copper hydroxide, copper naphthalate, basic copper oxychloride, copper sulfate, copper oxide, a mixture of oxine-copper and acid bayonet ( Bordeaux mixture), mancoopper, zinc mancozeb, maneb, meferimzone, mepanipyrim, mepronil, extinction Metalaxyl, metconazole, methasulfocab, methfuroxam, metiram, metomeclam, metsulfovax, medi Mildiomycin, myclobutanil, michaelin 15 (m yclozolin), dimethyldithiaminyl acid, nitrothal-isopropyl, nuarimol, ofurace, oxadixyl, oxo Oxamocarb, oxolinic acid, oxycarboxin, oxyfenthiin, paclibutrazole, pefurazoate, penconazole, Pencycuron, phosdiphen, pimaricin, piperalin, polyoxins, polyoxorim, probenazole, Prochloraz, procymidone, propamocarb, propanosine-sodium, propiconazole-21-200526611 (propiconazole), propineb, white powder Pine (pyrazophos), pyrifenox, pyrimithanil, pyroquilon, pyroxyfur, quinconazole, quintozene (PCNB ), Sulfur and sulfur preparations, 5 tebuconazole, tecloftalam , Tecnazene, tetcyclacis, tetraconazole, thiabendazole, thicyofen, thifluzamide, methyl-doxetrazine thiophanate-methyl), thiram, tioxymid, toclophos-methyl, tolyfluanid, triadimefon (triadimenol), triazbutil, triazoxide, trichlamide, tricyclazole, tridemorph, triflumizole, saif Triforine, triticonazole, uniconazole, validamycin A, vinclozolin 'zariianiide, zinc Zineb, Ziram and Dagger G, OK-8705, ΟΚ-88 (Π, α- (1,1-dimethylethyl) -β- (2-phenoxyethyl) _ιη 1,2,4-triazole small ethanol, α- (2,4-dichlorobenzyl) -0-fluoroglycyl-1 丙基 -1,2,4-trisial-1-ethanol, α- ( 2,4-dichlorobenzene 20-yl) -β-fluorenyloxy-a-methyl ] Hl, 2,4-triazole-1-ethanol, α- (5-fluorenyl-1,3-dioxan-5-yl) -β-[[4 · (trifluoromethyl) _phenyl ] -Methylene; μΗ-υ〆 · triazole small ethanol, (5RS, 6RS) -6-hydroxy_2,2,7,7_tetramethyl_5- (1Η-1,2,4-tri Azol-1-yl) -3-octanone, (E) -a- (methoxy-imino) _N-fluorenyl_2_phenoxy_phenylacetamidine, isopropyl 1- { 2-methyl small [[[[1_ (4_fluorenylphenyl) -ethyl] -amine-22- 200526611 yl l · M-yl] -propyltribenzyl carbamate, 1- (2,4- Dichlorophenyl) -2- (1Η-1,2,4-triazole_1-yl) _ethyl ketone 0_ (benzylfluorenyl) oxime, 1- (2-methyl1-naphthylfluorenyl- Crocodone_2,5_dione, 1- (3,5_dichlorophenyl) dong (2-propenyl) _2,5_pyrrolidinedione, fluorene (diiodomethyl) _sulfonylfluorene -Methyl-benzene, 5 [[2- (2,4-dichlorophenylphosphonium, 3-dioxane-2-yl] -methyl] -1fluorene-imidazole, fluorene [2- (4-chloro Phenyl) -3-phenyloxiranyl] -methyl] -1Η-12 4-triazole, 1- [1- [2-[(2,4-dichlorophenyl) _methoxy ] _Phenyl] vinyl] _ιΗ ^ 0, ^ methyl-5-nonyl-2_ (phenylmethylpyrrolidinol, 2,6, _dibromo | fluorenyl-4'-trifluoro Methoxy_4, _trifluoro-methyl_; [, hongthiazole_fluoranilide , 2,2-dichloro-ο-Ν-ΙΜ4-chlorophenyl) -ethyl] Sm-ethyl-3-methyl-cyclopropanecarboxamide, 2,6-dichloro-5- (methylthio) > 4-pyrimidinyl thiocyanate, 2,6-dichloro-N- (4-trifluoromethylphenylfluorenyl) -benzidine, 2,6-dichloro-N-[[4- (tri Fluorofluorenyl) -phenyl] -fluorenyl] -phenylhydrazine, 2- (2,3,3-triiodo-2-propenyl) -2fluorene-tetrazole, 2-[(1-methylethyl) _ Sulfonyl] -5- (trichlorofluorenyl) -1,3,4-thiadiazole, 2-[[6-deoxy-4-0- (4-0-15 methyl-β-D -Grapepyranosyl) -aD-Grapepyranosyl] -Amino] -4-methoxy-1H-pyrrolo [2,3-d] pyrimidin-5-fluoronitrile, 2-aminobutane Alkanes, 2-bromo-2- (bromomethyl) -pentanedicarbonitrile, 2-gas-N- (2,3_dihydro_1,1,3_trimethyl-1H-indan_4_yl) 3-pyridinecarboxamide, 2-gas-N- (2,6-diamidinophenyl) -N- (isothiocyanatomethyl) -acetamidamine, 2-phenylphenol (OPP), 3,4-trichloro small [4- (difluoromethoxy 20-yl) -phenyl] -1 fluorenyl-rotyl-2,5-dione, 3,5-digas-N_ [cyano-[( 1-methyl-2-propynyl) -oxy] -methyl] -benzimidamine, 3- (1,1-diamidinopropyl small keto-1H-ind-2-methanyl '3_ [ 2- (4-chlorophenyl) -5-ethoxy-3-iso11 oxasalidine] -π-pyridine, 4-chloro-2_cyano -N, N-dimethyl-5- (4-methylphenyl) -1'-imidazolium sulfonamide, 4-fluorenyl-tetrazolo [l, 5-a] quinazoline_5 (4Η ) _One, 8- (1,1-dimethyl-23- 200526611 ethyl) -N-ethyl_N-propyl-1,4-dioxaspiro [4 · 5] decane-2_ Methaneamine, 8-hydroxyquinoline sulfate, 9H-dibenzopyran-2 _ [(phenylamino)> carbonyl] -9-carboxylic acid hydrazine, bis- (1-methylethyl) 3-methyl ^^ [(3_methylphenylfluorenyl) _oxy] -2,5-thiophene dicarboxylic acid ester, cis_ι_ (4-chlorophenyl) -2- (1Η-1,2,4_tri Azole 5 -1 · yl) _cycloheptanol, cis_4- [3- [4- (1,1-dimethylpropyl) -phenyl-2-amidinopropyl] -2,6- Dimethyl-morpholine hydrochloride, ethyl [(4-chlorophenyl azide cyanoacetate, potassium osmium carbonate, methane tetrathiol sodium salt, methyl μ (2,3_dihydro- 2,2_dimethyl-1Η-imide-1_yl) _1Η-imidazole-5-carboxylic acid ester, methyl N- (2,6-diamidylphenyl) -N- (5_isoxazolyl Carbonyl) -DL_alanine, fluorenyl N- (chloroethenyl) · N_ (2,6_dimethylphenyl) -DL-alanine, N- (2,3_dichloro- 4-hydroxyphenyl) _1-fluorenyl-cyclohexanefluorenamine, N- (2,6-dimethylphenyl) -2-fluorenyloxy-N- (tetrahydro · 2-keto-3 · Fur ) -Acetamidamine, N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2-keto-3-thienyl) -acetamidamine, N- (2-chloro-4-nitrophenyl) -4-fluorenyl-3-nitro-benzenesulfonamide, N- (4-cyclohexylphenyl) -1,4,5,6-5 tetrahydro 2-pyrimidinamine, N- (4-hexylphenyl) -1,4,5,6-tetrahydro-2-pyrimidinamine, N- (5-air-2-amidinophenyl) -2-methyl Oxy-N- (2-keto-3-oxazolidinyl) -acetamidamine, N- (6-fluorenyloxy) -3-pyridyl] -cyclopropanehydrazine, Ν- [2, 2,2-Three-Gas Small [(Acetoethyl) -Amine] -Ethyl] -Benzamine, N- [3-Chloro-4,5-bis (2-propenyloxy) -phenyl] -N'-methoxy-methanediamine, N-formamyl-N-hydroxyi0-DL-alanine-sodium salt, 0, 〇_diethyl [2- (dipropylamino)- 2-ketoethyl l · ethylphosphoniumamidosulfate, 0-fluorenyl S-phenylphenylpropylphosphoniumamidosulfate, S-fluorenyl1,2,3-benzothiadi An azole-7-carbonyl sulfate, a spiro [2H] -1-benzopyran-2, Γ (3Ή) -isobenzofuran) -3'-one. -24- 200526611 bactericidal hydrazones bronopol, dichlorphen, nirapyrin, nickel dithiocarbamate, kasugamycin, octasone (Octhilinone), furancarboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulfate and other copper preparations. Insecticidal insecticides / Acaricides / Insecticidal insecticidesAbamitin, aephate, acetamiprid, acrinthrin, alanycarb , Aldicarb, aldoxycarb, alpha-cypermethrin, alphamethrin, amitraz, avermectin, AZ 60541 , Azadirachtin, azamethiphos, azinphos 15 A '' azinphos M, azocyclotin, bacillus popilliae, sphaericus, subtilis Bacillus, Sulgi, Baculoviruses, φ Beauveria bassiana, Beauveria tenella (white strong bacteria), benclothiaz, bendiocarb, benfuracarb, bensultap, west off (Benzoximate), B-type saponin 20 (betacyfluthrin), bifenazate, bifenthrin, bioethanomethrin, papomeline (1 ^ (^ 6111161: 111 ^ 11), Dimethoate (BPMC), bromophos A, bufencarb, buffenin (Buprofezin), butathiofos, butocarboxim, butylpyridaben, cadidone • 25- 200526611 (cadusafos), carbaryl, carbofuran ), Carbophenothion, carbosulfan, cartap, chloethocarb, chlorethoxyfos, chlorfenapyr, chlorofenap ( chlorfenvinphos), chlorfluazuron 5 '' chlormephos, chlorpyrifos, chlorpyrifos, M, chlovaporthrin, cis-resmethrin, cis-resmethrin -permethrin), clocythrin, clothothocarb, clofentezine, cyanophos, cycloprene, cycloprothrin, cyfluthrin ), Cyhalothrin, cyhexatin, cypermethrin, cyromazine, deltamethrin, demeton M, demeton S, Methionone-S-methyl, Diphendione (di afenthiuron), diazinon, dichlorvos, diflubenzuron, dimefluthrin, dimethoate, dimethylvinphos, diofen Diofenolan, disulfoton, docusat-sodium, dofenapyn, eflusilanate, emamectin, ebon Empenthrin, 20 endosulfan, Entomopfthora spp ·, esfenvalerate, ethiofencarb, ethion, ethoprophos , Etofenprox, etoxazole, etrimphos, fenamiphos, fenazaquin, fenbutatin oxide, fenbutatin-26 -200526611 (fenitrothion), fenothiocarb, fenoxacrim, fenoxycarb, fenpropathrin, fenpyrad, fenpyrithrin, fen Fenpyroximate, fenvalerate, Waipu (Fipronil), rich 5 miscellaneous jinan (fluazinam), fluazuron, flubrocythrinate, flucycloxuron, flucythrinate, flufenoxuron, Flutenzine '' fluvalinate, fonophos, fosmethilan, fosthiazate, fubfenprox, furathiocarb, 7 -cyhalothrin, granulosis viruses, halofenozide, HCH, heptenophos, hexaflumuron, hexythiazox, hydroprene, Yida Imidacloprid, isazofos, isofenphos, isoxathion, 15 ivermectin, nuclear polyhedrosis virus, lambda, cyhalothrin, lufenlon (lufenuron), marathion, mecarbam, metaldehyde, metamidophos, metharhizium anisopliae, metharhizium flavoviride, metidathion, methioc arb), nam 20 (methomyl), methoxyfenozide, metofluthrin, metolcarb, metoxadiazone, mevinphos, Milbemectin, Monocrotophos, Naled, Nitenpyram, Nithiazine, Novalon-27- 200526611 (novaluron), Ou Misong omethoat), oxamyl, oxydemethon M, Paecilomyces fumosoroseus, Parasson A, Parasson M, permethrin, phenthoat, blessing Phorate, phosalone, phosmet, phosphamidon, phoxim, pirimicarb, pirimiphos A, Atlas M, profenofos, potassium oleate, prallethrin, profluthrin, promecarb, propoxur, prothiofos, general Prothoate, pymetrozine, 10 pyraclofos, pyresmethrin , Pyrethrum, pyridaben, pyridathion, pyrimidifen, pyriproxyfen, quinalphos, ribavirin , Salithion, sebufos, silafluofen, spinosad, sulfotep, sulprofos, sleeve-forhuali ( tau-fluvalinate), tebufenozide, tebufenpyrad, tebupirimiphos, teflubenzuron, tefluthrin, temephos, Temivinphos, terbufos, tetrachlorvinphos, theta-cypermethrin, thiamethoxam, thiapronil, thiatriphos (Thiocyclam), thiodicarb, thiofanox, thuringiensin, tralocythrin, tralomethrin, triarathene ， Sanzamet -28- 200526611 (triazamate) ophos), triazuron, trichlophenidine, trichlorfon, Trichoderma atroviride, triflumuron, trimethacarb, vamidothion, Vaniliprole, Verticillium 5 lecanii, YI-5302, zeta-cypermethrin, zolaprofos, (1R-cis)-[5 · (phenylfluorenyl) -3-furanyl] -methyl 3 · [(dihydro-2-keto-3 (2H) -furandiyl) _fluorenyl] _2,2-dimethylcyclopropanecarboxylate '(3- Phenoxyphenyl) -methyl 2,2,3,3-tetramethyl-cyclopropanecarboxylate, 1-[(2-chloro-5-thiazolyl) fluorenyl; | tetrahydro-3,5 _Difluorenylnitrosene 3,5-ίο Sangen · 2 (1Η) _imine, 2- (2-chloro-6-fluorophenyl) -4- [4- (1,1-dimethyl Ethyl) phenyl] -4,5-dihydro-oxazole, 2- (acetamyloxy) _3-dodecylnaphthalenedione, 2-chloro-N-[[[4- (l- Phenylethoxyphenyl] _amino] _carbonyl] -phenylhydrazine, 2-gas-N-[[[[4- (2,2-dichloro] behendifluoroethoxyphenyl] -amine [Provinyl] -benzylamine, 3-fluorenylbenzylpropylcarbamate, 4- [4_ (4_ethoxybenzene15ylfluorenylpentyl] small fluorobenzyl -Benzene, 4-Gas-2- (l, l-difluorenylethyl) -5-[[2- (2,6-difluorenylbenzyloxybenzyloxy) _ethyl] sulfur] -3 (2 office olfactory phase, 4-chloro-2- (2-Gamomethylpropyl) j [(6_iododonyl) -methoxy] -3 (2H) -Da, 4 | 5 _ [(6ϋσΛϋ 定 基) methoxy] dong (3,4_dichlorophenyl) _3 (2H) _norphinone, Suli strain EG_2348, phenylfluorenyl 20 small 0 behenediylethyl > Stupid carboxylic acid, 2, difluorenyl-3- (2,4-dichlorophenyl) -2-one small oxaspiro [4. 5] dec-3K-butyric acid vinegar, [3-[(6n pyridyl) fluorenyl] -2-oxazolidinediyl] _cyanofluorendiamine, dihydro_2_ (nitro_methylene) -2Η-1,3 Lingjing-3 (4Η) -Mepan, ethyl [2- [Tetrahydrodione-keto (benzylmethyl) -4 ♦ well] oxy] ethyl [aminocarboxylic acid Esters, N_ (3,4,4-trifluoroketone group-29- 200526611 _3-butenyl) -glycine, N · (4-chlorophenyl) _3- [4_ (difluorofluorenyloxy) PhenylH, 5-dihydro-4-phenylfluorenamine, N · [(2-chloro · 5_fluorenyldimethyl] I methyl-N ,,-nitrophosphoniummethyl is called methyl_ 2_Acryl) · 1,2 · Hydroxydiamine thiamine, N-fluorenyl_N, _2_propenylbishydrazine diethylthiothiamine diethyl [2renylamino) · 2,2-ethyl] -ethyl stuffed amino sulfate. The active compounds of the present invention can be converted into conventional formulations and used in the field of crop protection 'for example' to make them soluble, emulsions, wettable powders, water-dispersible granules, suspensions , Powders, foams, foams, pastes, granules, natural and synthetic substances impregnated with active compounds, microcapsules, fumigants, etc. These formulations can be formulated according to known methods, for example, mixing active compounds with extenders, that is, liquid, liquefied gas, or solid diluents or carriers, and optionally using surface-active agents, i.e., emulsifiers and And / or dispersant and / or foaming agent; if the extender used is water, it can also be used, for example, organic solvents as auxiliary solvents; suitable liquid solvents are mainly: aromatic hydrocarbons, for example, difluorene Benzene, toluene, alkyl naphthalenes, etc .; vaporized aromatics and chlorinated aliphatic hydrocarbons ', for example, chlorobenzene, vinyl chloride, or dichloromethane; aliphatic hydrocarbons, such as' cyclohexane Or paraffin, for example, mineral oil, mineral or vegetable oil, alcohols, such as butanol or glycol, but also ethers and esters, ketones, such as acetone, methyl ethyl steel, methyl Isobutyl ketone or cyclohexanone, strong polar solvents, such as t-dimethyl methylamine and dioxin, also include water. Liquid diluents or carriers can be, for example, aromatic hydrocarbons (eg, dimethyl-30-20 200526611 benzene, toluene, or naphthyl naphthalene, etc.), chlorinated aromatics or chlorinated aliphatic hydrocarbons. Type (such as' chlorobenzenes, vinyl chloride or methylene chloride, etc.), aliphatic hydrocarbons (such as cyclohexane, etc. or stone coffee, such as mineral oil division, etc.), alcohols (such as butanol, glycol And its members, vinegars, etc.), Ming (such as propane, methyl ethyl, methyl isobutyl, cyclohexanone), strong polar solvents (such as' dimethylformamide, Disulfoxide, etc.), water, etc. 10 15 20 Liquefied gaseous diluent or carrier means a liquid that is a gas at standard temperature and pressure. Examples that may be mentioned are, for example, gaseous solution propellants such as butane, propylene, nitrogen and carbon dioxide. Toothed smoke. … Appropriate solid dilution counts, such as finely divided natural minerals (such as high-territory, dry soil, talc, white ridge, quartz, American activated white clay, montmorillonite, etc.) (For example, highly dispersed, alumina and silicates, etc.) and so on. Suitable solid carriers for the preparation of granules are, for example, comminuted and unrefined natural rocks (eg, calcite, marble, pumice, * fossil 2/3, etc.), synthetic organic and inorganic particles , Organic material particles = eg sawdust, coconut husks, corn cobs, tobacco stems, etc.), etc. Suitable emulsifying and / or foaming agents that can be mentioned are, for example, the emulsifiers with anions, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, such as alkyl Aryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates, etc., dihydrolysates, and the like. * White water dispersant includes, for example, lignin sulfurous acid waste liquid, methyl cellulose, etc. 0-31-200526611. Adhesives (powder, granules, emulsifiable concentrate) can also be added to the formulation. 'Useful binders that may be mentioned are, for example, carboxymethyl cellulose, natural and synthetic polymers (eg, gum arabic, polyvinyl alcohol, polyvinyl acetate, etc.). 5 Can also be used by the user's toners. For example, inorganic pigments (for example, iron oxide, titanium dioxide and Prussian blue, etc.), organic dyes, such as alizarin dyes, azo dyes, etc. Or metal phthalocyanine dyes, and micronutrients, such as iron, manganese, butterfly, copper, Ming, molybdenum, and other salts. 10 This formulation may contain the above-mentioned active compound, and its content is usually between 0. The range of 1-95% by weight is preferably between 0.5-90% by weight. The formulations and possible application forms of the present invention will be illustrated by the following more specific examples. The active compounds according to the invention not only act against harmful organisms that harm plants 15, but can also be used in veterinary medicine against animal parasites (ectoparasites), hard ticks, soft ticks, mangeworms ( mange mites), leaf mites, blue ropes (ding rope and tongue rope), parasitic rope sisters, lice, head lice, feather lice, and fleas, such parasites include: Anoplurida '' such as beasts Spp.), Linognathus spp., Pedicuus spp. ), Genus spp. ) And spp .; Mallophagida and Amblycerina and Ischnocerina, such as the hairy bird lice spp., Chicken (feather) lice spp. ), Colossus spp ·), Botanus spp ·), -32- 200526611 spp ·, Lepikentron spp.  , Damalina spp. , TWc / ioi / ecies spp ·) and genus spp ·); Diptera and Nematocerina and Brachycerina, such as Aedes spp ·), Anopheles mosquitoes 5 spp ·), Culex mosquitoes (CWex spp ·), Polygonum spp ·), five spp.  »(Phlebotomus spp. ) 5 Lutzomyia spp.  ^ (Culicoides spp. ), Chrysops spp. ), Hybomitra spp.  5 Atylotus spp.  5 M {Tabanus spp ·) »Haematopota spp ·, corpse / π · / φ (9 /« > 7 · ίζ spp ·, genus bee fly (10,000 rflw / iz spp ·), family rope genus (Mw * sca 10 Spp ·), Spp ·), genus (5Ϊ (9772 (9χ) Λ? Spp ·), jk fly (Haematobia spp. ) j (Morellia spp. ) 5 {Fannia spp. ) ^ Genus G7os ^ / «iz spp ·), genus Cfly /////? / Zon3 spp · L ·, Lucilia spp ·, Chrysomyia spp. , Wohlfahrtia spp. , Carnivora 〇Sflrcc7? / Zag (2 spp ·), Rana spp ·), Leather Rope 15 spp ·), Gastronomy spp ·), Hippobosca spp. ), Lipoptena spp. With Melophagus spp.  ·, Fleas B (Siphonapterida), such as human fleas (cadaver w / ex spp ·), genus Flea (C7e «oce /? / ^ // i / e» s spp ·), oriental rat fleas spp · ) And flea genus spp ·); Heteropterida, such as bed bug 20 (C7mex spp ·), vampire spp ·), spp · and brown leaf spp ·); Blattarida), for example, Oriental magpie (Fang / Jiaru orientalis), American cockroach (Periplaneta, German cockroach CS / aMe / izgermaw / cfl), and / ^ // (2 spp ·; tick full subclass (Acaria , Acarida) and posterior chest valve and middle chest valve (Meta-33- 200526611 and Mesostigmata), such as Cryptosporidium sp. , Hard ticks (/ xoi / es spp ·), flower ticks spp ·), bovine ticks (J? (9 (? / 7 / n7w * s spp ·), leather ticks spp), bloodthirsty ticks 5 spp ·), water ticks (/ fyfl / omwiz spp ·), cephalosporus (and / ^ / ^ cepAir / ws spp ·), genus Goose (i) erw (2 «3; Mw * s spp ·), And Γπ7 / ζ · βίζ · α spp ·, Pneumonyssus spp.  ^ Sternostoma spp. J ^ Varroa spp.  ; Actinedida and Acaridida, for example, the bee trachea M (Acarapis spp.), Cheyletiella spp. Ornithocheyletia 10 spp ·, Ascaris (MγοΜα spp ·), / Ascaris (Merrgaia spp ·), Demodex spp ·, Trombicula spp ·, Furus {Listrophorus spp ·), deearie spp ·, Tyrophagus spp. ), Caloglyphus spp ·, Hypodectes spp ·, Pterolichus spp ·, Psoroptes spp ·, Chorioptes spp ·, Otodecies spp ·, squeezed ends Genus OSarcc ^ es spp ·), cephalosporin spp ·), Knemidocopies spp ·, Cytodites spp. ) And Laminosioptes spp. 〇 The active compound of formula (I) of the present invention is also suitable for controlling arthropods that invade livestock with agricultural 20 productivity, including, for example, cattle, sheep, goats, horses, Pigs, mules, camels, buffalos, rabbits, chickens, turkeys, ducks, geese and bees, other pets such as dogs, cats, cage birds and ornamental fish, and so-called experimental animals such as golden rats, guinea pigs, rats and Mice, by controlling these arthropods, reduce death events and productivity (eg -34- 200526611 5 10 15 meat, milk, wool, fur, eggs, honey, etc.), resulting in a reduction in production by using the The active compounds are better managed with higher economic value and more calmness. The active compounds according to the invention are used in veterinary medicine and are administered in the intestine in a known manner, for example, as lozenges, capsules, single doses, potions, granules, pastes, boluses, Through feed and suppositories, etc .; for parenteral administration, for example, by injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implantation, nasal administration, transdermal type, such as immersion or Bathing, spraying, pouring and spotting, washing and powdering can also be aided by mouldings containing active compounds, such as collars, earrings, tail rings, limb bandages, reins, marker designs, etc. When used for cattle, poultry, pets, etc., the active compound according to the formula ⑴ of the present invention is used in the form of a formulation, such as a powder, an emulsion, a free-flowing composition, which contains the amount of the active compound according to the present invention as 1 to 80% by weight, used directly or diluted 1000 to 10,000 times, or they can be used as a chemical bath.

20 The medicament of the present invention is suitable for controlling pathogenic endoparasites encountered in the following situations: human and animal management and livestock breeding, productive livestock, breeding livestock, zoo animals, laboratory animals, For experimental animals and pets, and these compounds have low toxicity to warm-blooded animals, they are effective against all or some stages of pest development, and they are resistant to resistant or generally sensitive Breeds, by suppressing pathogenic endoparasites, to reduce disease, lethality and yield (such as the productivity of meat ", =, wool, fur, eggs, honey, etc.), make use of

-35- 200526611 This active compound may obtain greater economic benefits and simpler animal management. The pathogenic endoparasites include cestodes, trematodes, nematodes and acantocephales, especially ... Pseudophyllidea, for example, DiphyUoboihrium spp., Spiromira spp. 'Schistocephalus spp., Ligula spp ·, Bothridium spp ·, spp ·; Cyclophyllidea, for example, Mesocestoides spp., Paranoplocephala spp. ^ Moniezia spp. 5 Thysanosomsa 10 spp., Thysaniezia spp., Avitellina spp. Stile. Cittotaenia spp. 5 Andyra spp. 5 Bertiella spp. 9 Taenia spp. ^ Echinococcus spp., Hydatigera spp., Davainea spp. 5 Raillietina spp. 5 ^ {Hymenolepis spp.? spp. »Echinocotyle spp. 5 Diorchis spp. J 15 Canine (Melon) Ascaris spp.), spp., spp .; Monogenea, for example, ogen spp. Spp ·), spp ·; Digenea, for example, spp. 5 Posthodiplostomum spp. J ^ A & ^ Schistosoma spp.) ^ 20 Trichobilharzia spp.? Omithobilharzia spp. ^ Austrobilharziato spp. spp., Leucochloridium spp., Brachylaima spp., Echinostoma spp., Echinoparyphium spp., Echinochasmus spp., Hypoderaeum spp., Fasciola spp. ^ Fasciolides spp.pp. loc. 266-36 ^-266 ^ ^-266 ^ ^ Cys ^^

Typhlocoelum spp., P ar amp hi sto mum spp., Calicophoron spp. »Cotylophoron spp. 5 Gigantocotyle spp.? Fischoederius spp ·, spp ·, poultry intestinal fluke (iVWoci? 印 / w * s sppis · s), Cata . »Plagiorchis spp. 5 Prosthogonimus spp., 5 Dicrocoelium spp.» Eurytrema spp. 1 Troglotrema spp., Paragonimus spp. »Collyriclum spp., XNanophyetus spp. 5 Clonor spps. 5 Clonor. ^ spp ·, MeiflgOw / wws spp ·; Enoplida, for example, whipworm spp ·), capillary nematode spp ·), i0spp ·, trichinella (7 > / c / n'we // fl spp ·); Rhabditida 5 j Micronema spp. j Strongyloides spp ·; Strongylida, for example, Fen Plant ⑽ 少 / like spp ·, 7 > 7 (9 Offices "0/7 / ^ Cantonese spp., Oesophagodontus spp.5 Trichonema spp. ^ Gyalocephalus spp., Cylindropharynx spp., Poteriostomum spp., 15 Cyclococercus spp.5 Cylicostephanus spp. 5 Oesophagostomum sap.pp pp. » spp.), Uncinaria spp.), Bunostomum spp., Globocephalus spp. ^ Syngamus spp., Cyathostoma spp., Metastrongylus spp. ^ Dictyocaulus spp. 5 Muellerius spp. »20 Protostrongylus spp.» Neostrongylus spp.? Cyylscaca sylloca spp. 5 Elaphostrongylus spp., Par elaphostrongylus spp., Crenosoma spp., Paracrenosoma spp . 5 Marshallagia spp. 5

Cooperia spp. ， Nematodirus spp · ’Hyostrongylus spp.

Obeliscoides spp. 5 Amidostomum spp. J Ollulanus spp. \ &Amp; head (Oxyurida), 4 columns such as, Oxyuris spp ·, Enterobius spp., 5 Passalurus spp · 5 Syphacia spp. 5 Aspiculuris spp.? Heterakis spp. Ascaridia, for example, Ascaris spp. 5 Toxascaris spp. 5 ^ {Toxocara spp.) 9 Parascaris spp. J Anisakis spp. 5 AcizrWa spp ·; Spirurida, such as Gnathostoma spp.), Physaloptera spp., eye A (Thelazia i〇spp ·), beautiful esophagus (Go »g less / owema spp ·), gastric nematode spp.) j Parabronema spp.? Draschia spp. ^ Dracunculus spp .; Filariida order, for example, Fen spp., Spp ·, Setaria spp. ^ Loa spp. ^ Dirofilaria spp. »Litomosoides spp. 5 spp ·, Fwc / iererifl spp ·, spp ·; Gigantorhynchida 15 (for example , Trichomonas spp. (/ ^ 7 化 0 // 以 Spp), Moniliformis spp., Macrocanthorhynchus spp., Leptospira spp. Livestock and breeding animals include mammals, such as, for example, cattle, horses, sheep, pigs, goats, camels, buffalo, mule, rabbit, brown deer, reindeer, fur animal, such as, for example, mink, eider or Raccoons, birds, such as chickens, geese, turkeys, ducks or ostriches, freshwater and marine fish, such as trout, carp, and eel, reptiles and insects, such as bees and silkworms, laboratory and experimental animals Including mice, rats, guinea pigs, golden rats, dogs and cats, pets include dogs and cats. -38- 200526611 Administration can be administered as a preventive and therapeutically effective method. The administration of the active compound can be directly or made into a suitable formulation 'through the intestine, parenteral tract, skin, nose, treatment of the living environment or as a shaped article (such as a bar, Boards, straps, collars, earrings, limb bandages or marker designs) are administered. Active compounds for enteric administration include the following types of active compounds for oral administration: powders, lozenges, capsules, ointments, drinks, granules, solutions, suspensions and emulsions, orally, bolus Medicine, medicated feed or drinking water; it can also be administered transdermally, for example, as an infusion, spray, or poured or spotted, or through non-gastrointestinal fun 'For example, the injection form is administered by intramuscular, subcutaneous, intravenous or intraperitoneal injection or implantation. Suitable formulations include: solutions, such as solutions for injection, oral solutions, concentrated solutions for oral dilution, solutions for skin or body cavity, when poured into the formulation 'gel, for oral or dermal application Emulsions or suspensions; preparations of semi-solid bears; active compounds are formulated in ointment bases or in oil-in-water or water-emulsion-oil emulsion bases; solid preparations, for example, powders Premixes or concentrates, granules, pills, lozenges, boluses, capsules; gas spans and inhalants, shaped articles containing active compounds, solutions for intravenous, intramuscular and subcutaneous injection The preparation method of solutions for injection is to dissolve the active compound in a suitable solvent, and it is necessary to add additives, such as co-solvents, acids, test, buffered dark-39-200526611, anti- Oxidant, or preservative 'This solution is sterilized_filtered and filled into a container. Suitable solvents include: physiologically acceptable solvents such as water, alcohols such as ethanol, butanol, benzyl alcohol, glycerol, propylene glycol, polyethylene glycol, and N-fluorenyl-pyrrolidone, and mixture. Suitably, the active compound may also be dissolved in a physiologically acceptable vegetable or synthetic oil suitable for injection. Suitable co-solvents include solvents that help the active compound dissolve in the main solvent or solvents that prevent precipitation of the active compound. Examples of solubilizers are polyvinylpyrrolidone, polyethoxylated castor oil Polyethoxylated sorbitol esters. The following are preservatives: benzhydryl alcohol, trifluorobutanol, p-acrylic acid esters or n-butanol. The oral solution is directly administered. The concentrated solution is first diluted to a concentration of 15 degrees in the tray and then administered orally. The preparation method of the oral solution and the concentrated solution is the same as that of the solution for injection, except that the sterilization step is not necessary. . The solutions for use on the skin are applied dropwise, applied flat, rubbed, spilled or sprinkled. These solutions are also prepared in the same manner as the solutions for injection described above. 20 In the preparation process, it may be advantageous to add thickeners. The following are examples of thickeners. • Bentonite, colloidal silica, aluminum monostearate, or organic thickeners, such as cellulose derivatives Substances, polyvinyl alcohols and copolymers, acrylates and methacrylates. The gel is applied to the skin or smeared flat or introduced into the recess of the body. 200526611 Depression, the preparation method of condensing μ & injection > is to add an appropriate amount of thickener to the preparation of the combination as described above. In the solution prepared by the method, the thickening agent used to form a clear, thick, ointment-like viscosity is described above. On the skin, the formulation on the skin and the skin is a skin bag's tongue compound that has been applied or splashed into a limited area, and penetrates the skin and acts on the whole body. 10 15 The preparation method of the chemical active point is prepared by dissolving, suspending, or in milk. The suitable compound can be put into an appropriate skin tolerable solvent or a mixture of solvents. The suction can also add other auxiliary substances. , For example, colorants, quotients, antioxidants, photolytic stabilizers or thickeners. Polyols include: water, alcohols, glycols, polyethylene glycols, or benzyl alcohol, glycerol, aromatic alcohols, for example, benzyl alcohol, benzyl alcohol, benzyl alcohol, For example, 'Ethyl Acetate', Butyl Acetate or Benzoyl Acrylate, for example, Class 1 'For example, ethylene glycols, such as diethylene glycol monomethyl ether or diethylene glycol mono-butyl ether, Ketones, for example, propionate

Ethyl fluorene 'aromatic and / or aliphatic hydrocarbons, plant or synthetic / derivatives, U i ^ ivir 1f-ethylamidine, N-methylpyrrolidone, or 2,2-dimethylamine Soil, 4'oxy-methylene-1,3-dioxolane. Colorants are all colorants that can be dissolved or suspended and allowed to be used in animals. Examples of absorption enhancers are DMSO, dispersed oils, for example, isotetradecanoate, dipropylene glycol nonanoate, silicone oils, fatty acid esters M, diglycerides or fatty alcohols. Antioxidants are as follows: sulfites or metasulfites, for example, potassium sulfite, ascorbic acid, butylhydroxytoluene, butylhydroxyanisole 20 200526611 or tocopherol. One photolytic stabilizer that may be mentioned is novantisolic acid. The acetone stabilizers are, for example, cellulose derivatives, starch derivatives, 5 polyacrylates or natural polymers, Examples are alginates or animal gums. Emulsions can also be administered orally, dermatologically or by injection. Emulsions can be water-in-oil type or oil-in-water type. They are prepared by dissolving the active compound in a hydrophobic or hydrophilic phase and using other The solvent of the phase homogenizes this phase with the aid of a suitable emulsifier; and, other suitable additives such as colorants, absorption enhancers, preservatives, antioxidants, photolytic stabilizers, and Increase dry matter. Suitable hydrophobic phases (oleaginous) include: paraffin oils, silicones, natural vegetable oils such as sesame oil, almond oil or castor oil, synthetic triglycerides such as caprylic / capric diglycerides, C8_12 vegetable fat 15 acid or other specially selected natural fatty acid triglyceride mixture, which may contain hydroxyl groups of saturated or unsaturated fatty acid partial glycerides, and C8 / C1G fatty acid mono- And mixtures of di-glycerides, fatty acid esters, such as ethyl stearate, di-n-butylfluorenyl fatty acid ester, hexyl laurate, dipropylene dinonanoate, with a branch of medium chain length Esters of chain fatty 20 acids and saturated fatty alcohols with a chain length of c16-c18, isopropyltetradecanoate, isopropyl palmitate, octanoic acid with a chain length of C12-C18i saturated fatty alcohols / Decanoates, isopropyl stearate, oleyl oleate, decyl oleate, ethyl oleate, ethyl lactate, waxy fatty acid esters, such as artificial duck tail fat gland fat , Dibutylphenylarsonate, dipropyl fertilizer-42- 200526 611 acid esters, related to subsequent ester mixtures, etc .; fatty alcohols such as isotridecyl alcohol, 2-octyldodecanol, cetylstearyl alcohol or oleyl alcohol; fatty acids such as , Oleic acid and its mixture. Suitable hydrophilic phases include water, alcohols, for example, propylene glycol, glycerol, 5 sorbitol, and mixtures thereof. Suitable emulsifiers include non-ionic surfactants such as polyethoxylated castor oil, polyethoxylated sorbitol monooleate, sorbitol monostearate, glycerol monostearate , Polyoxyethyl stearate or alkylphenol polyglycol ethers. 10 Amphoteric surfactants, such as N-lauryl-β-imino dipropionate or lecithin. Anionic surfactants, for example, sodium laurate, fatty alcohol ether sulfates, and monoethanolamine χτ / Ε. Salts of mono / didialkyl polyglycol ether orthophosphate. 15 Cationic-active surfactants, for example, cetyltrimethylammonium chloride. Suitable other adjuvants include: substances that increase the viscosity and stability of the emulsion, such as carboxymethyl cellulose, methyl cellulose and other cellulose and starch derivatives, polypropylene esters, alginates, Animal gum, acacia gum, polyvinylpyrrolidone, polyvinyl alcohol, methyl vinyl ether / maleic anhydride copolymer, polyethylene glycol, wax, colloidal silica, or a mixture of these substances. Suspensions are administered orally, dermatologically or by injection. They are prepared by floating the active compound in a liquid excipient and suitably adding other adjuvants, such as wettable agents, colorants, absorption enhancers, and preservatives. Anti-43-200526611 oxidants and photolytic stabilizers, suitable liquid excipients include all homogeneous solvents and solvent mixtures, suitable wettable agents (dispersants) include the aforementioned surface active agents, appropriate other auxiliary agents Include those shown earlier. Semi-solid formulations can be administered orally or dermatologically. They differ from the 5 suspensions and emulsions described above in their southerly lumpy nature. To prepare a solid-cell preparation, the active compound is mixed with an appropriate excipient, suitably, an adjuvant is added, and the mixture is formulated as described above. Suitable excipients include all physiologically acceptable solid inert substances, suitable for this purpose are inorganic and organic substances, inorganic substances are, for example, general salts, carbonates, such as calcium carbonate, carbonic acid, Alumina, silica, clay, precipitated or colloidal silica, and phosphates. Organic substances are, for example, sugar, fiber, food and animal feeds, such as milk powder, animal scraps, cereal flour, coarse bran and starch. 15 Auxiliaries are preservatives, antioxidants and colouring substances as described above. Other suitable auxiliaries are lubricants and slip agents, for example, magnesium stearate, stearic acid, talc, bentonite, disintegrants, such as starch or cross-linked polyvinylpyrrolidone, binders, such as starch Animal glue or linear polyethylene 20 ketrolone, with a dry binder such as microcrystalline cellulose. In these preparations, the active agent may also exist in the form of a mixture with a synergist or other active compounds that are resistant to pathogenic endoparasites. Examples of such active compounds are L-2,3,5,6- Tetrahydro-6-phenyl-imidazolium is well-known, and benzoate is also aminoammonium ester or pyrantel. 200526611 Ready-to-use preparations contain from ppm to 20% by weight of active compound, preferably from 0.1 to 10% by weight. ^ 0.5 Formulations diluted before use contain active compounds to 90% by weight, preferably from 5 to 50 ° / 至 by weight. 'Also, it is generally found that it is advantageous to reduce the mixture of the invention' by applying about 10 mg to about 10 mg per kg of body weight per day.

Very good results are obtained with the active compounds, preferably from 10 to 50 mg of active compound mixture per kg. In the composition, the weight ratio of praziquantel and / or epsiprantel to depsipeptide is usually 1: 1-10, preferably 1: 1_2 and very preferably 1 :1. The formulations and applications of the compounds of the present invention will be described more clearly with the following examples and test examples, however, the present invention should not be limited to these examples; unless otherwise specified, "parts" means "parts by weight" 'Is the basis of calculation. 15 Examples Synthesis Example 1

s / (CH2) 4CH = CF2 Put acetonitrile (100 ml) with 5-fluorenylthio ^ 2,4-thiadiazole (0.35 g), 1-fluorenylsulfonyl-oxy-6,6-difluoro -5-hexene (0.7 g) was mixed with potassium carbonate (0.5 g), heated under reflux for 4 hours, the reaction solution was cooled to room temperature, and then filtered with suction. -45-20 200526611 The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (eluent: ethyl acetate: hexane = 1: 9) to obtain colorless, oily 5- (6,6-difluoro-5-hexenylthio-1, 2,4-thiadiazole (0.55 g, yield 79%, nD2 ° = 1.5093). 5 Synthesis Example 2

(CH2) 4CH = CF2 10 Dissolve 5_ (6,6 · Digas · 5-Hexane · Hydroxythio-1,2,4-σsedionine (0.4 g) in methylene chloride ( 100 ml), and under ice-cooling, m-chloroperbenzoic acid (0.9 g, approximately 70% purity) was added, and the mixture was stirred at room temperature for 20 hours. This reaction solution was saturated with hydrogen carbonate. The aqueous sodium solution (50 ml) was washed twice, and the organic layer was dried over magnesium sulfate. After the solvent was distilled off under reduced pressure, the residue was purified by column chromatography (eluent: ethyl acetate: hexane = 1: 9) to produce colorless, oily 5- (6,6_difluoro-5_hexenylsulfonyl) -1,2,4-thiathiazolyl (0.25 g, yield 55%) , ND2G = 1.4999). Synthesis Example 3

(CH2) 4CH = CF2 in 5- (6,6-difluoro-5-hexylthio) -3-fluorenyl-1,2,4-thiadiazole (0.5 g) -46- 20 200526611 After dissolving in dichloromethane (100 ml), m-chlorobenzoic acid (0.5 g, purity about 70%) was added under ice cooling, and the mixture was allowed to stand at room temperature for an hour. Sodium hydrogen solution (5 (1 ml), and the organic layer was dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The product was purified by column chromatography (fluid washing solution: ethyl acetate · hexane spoon oil) 5- (6,6-difluoro-5-hexenylidene) -methylmethyl-2-dioxo (0.5 g, yield 94%, nD2i) = 1.511 0). According to the above Prepared in a similar way, the compounds of '2 and 3 are shown together;: =' and in Table M, Me represents methyl, 玢 Table 1. Group, iso-Pr represents isopropyl, n_B n-Pr represents N-propane, BU ^^ represents cyclopropyl, Cy_I > en represents-epi-n-pentyl, cy_Pr ph-epiphenyl. Substitute amyl 'cy for cyclohexyl, and 200526611 Table 1

R VN, —IN person S 'S (0) n (CH2) mCH = CF2 (I) | Compound number_ P Melting point or 1 Η 0 3 2 Η 1 3 3 Η 2 3 4 Η 0 4 1.5093 5 Η 1 4 1.5159 6 Η 2 4 1.4999 7 Η 0 5 8 Η 2 5 9 Η 0 6 1.5137 10 Η 1 6 11 Η 2 6 1.4920 12 Η 0 7 13 Η 0 8 1.5069 14 Η 1 '1 8 15 Η 2 8 1.4879 16 Η 0 9 17 Η 0 10 18 Η 2 10 19 Me 0 3 20 Me 0 4 1.5150 21 Me 1 4 1.5110 22 Me 2 4 1.4915 23 Me 0 6 24 Me 1 6 25 Me 2 6 26 Me 0 8 27 Me 1 8 28 Me 2 8 -48- 200526611 29 Et 0 4 30 Et 1 4 31 Et 0 6 32 Et 0 8 33 n-Pr 0 4 34 n-Pr 2 4; 35 n-Pr 0 6 36 iso-Pr 0 4 37 iso -Pr 1 4 38 n-Bu 0 4 39 n-Bu 0 8 40 sec-Bu 0 4 41 sec-Bu 1 6 42 t-Bu 0 4 1.5048 43 t-Bu 1 4 1.4835 44 t-Bu 2 4 1.4835 45 t-Bu 2 8 46 n-Pen 0 4 47 cy-Pr 0 · r 4 48 cy-Pr 1 4 49 cy-Pr 2 4 50 cy-Pr 0 6 51 cy-Pr 0 8 52 cy-Pen 0 4 53 cy-Pen 1 4 54 cy-Hex 0 4 55 cy-Hex 2 4 56 MeOCH2 0 4 57 MeOCH2 1 4 58 MeOCH2 2 4 59 MeOCH2 0 6 60 EtOCH2 0 4 61 EtOCH2 2 4 -49- 200 526611 62 iso-PrOCH2 0 4 63 iso-PrOCH2 0 8 64 MeSCH2 0 4 65 MeSCH2 1 4 66 MeSCH2 2 4 67 EtSCH2 0 4 68 EtSCH2 1 4 69 iso-PrSCH2 0 4 70 iso-PrSCH2 2 4 71 C1CH2 0 4 72 cich2 1 4 73 cich2 0 6 74 cich2ch2 0 4 75 C1CH2CH2 1 4 76 C1CH2CH2 0 8 77 cf3 0 4 78 cf3 1 4 79 cf3 2 4 80 cf3 0 6 81 cf3 0 8 82 cf3cf2 0,: 4 83 CF3CF2 0 6 84 MeO 0 4 1.5225 85 MeO 1 4 1.5141 86 MeO 2 4 1.4959 87 EtO 0 4 88 EtO 2 4 89 iso-PrO 0 4 90 iso-PrO 1 4 91 MeS 0 4 92 EtS 0 4 93 iso-PrS 0 4 94 PhCH2 0 4 -50- 200526611 Sleep Compound Number Session 1-: VV-. '\ ≪ > ^ Melting point or n〇2〇M 95 PhCH2 1 4 96 PhCH2 2 4 97 PhCH2 0 6 98 4-F-PhCH2 0 4 99 2-Cl-PhCH2 0 4 100 4-Cl-PhCH2 0 4 101 4-Br-PhCH2 0 4 102 3 (FrPhCH2 0 4 103 4-CF3-PhCH2 0 4 104 4-CF3-PhCH2 0 8 1 105 4 -CF3-PhCH2 1 .......... 1 8 \ 106 4-Me-PhCH2 0 4 107 4-Me-PhCH2 2 4 108 4-MeO-PhCH2 0 4 109 4-MeS-PhCH2 0 4 110 2,4-diClPhCH2 0 4 111 2,4-diMePhCH2 0 4 112 Ph 0 4 1.5750 113 Ph 1 4 1.5770 114 Ph 2 4 1.5558 115 Ph 〇6 116 Ph 0 8 117 2-F-Ph 0 4 118 3-F-Ph 0 4 119 4-F-Ph 0 4 120 2-Cl-Ph 2 4 121 3-Cl-Ph 0 4 122 4-Cl-Ph 0 6 123 4-Br-Ph 0 4 124 4-Br-Ph 1 4 125 4-CF3-Ph 0 4 126 4-CF3 1 4 127 4 -CF3 2 4 -51-200526611

128 4-CF3 0 6 129 3-Me-Ph 0 4 130 4-Me-Ph 0 4 131 4-Me-Ph 0 8 132 4-MeO-Ph 0 4 133 4-MeS-Ph 0 4; 134 2, 4-diCl-Ph 0 4 135 3,4-diCl-Ph 0 .4 136 2,4-diMe-Ph 0 4 137 Cl 0 4 1.5395 138 Cl 1 4 1.5305 139 Cl 2 4 1.5098 140 Cl 0 6 141 Cl 0 8 142 Br 0 4 143 Br 2 4 144 2-furyl group 0 4 145 2-thienyl group 0 4 146 丨 3-thienyl group 0 4 147 5-Methenyl-2-yl group 0 4 148 5-methyl plug Phen-2-yl 0 4 149 4,5-dibromothiophen-2-yl 0 4 150 2-pyridyl 0 4 151 3-pyridyl 0 4 152, 4-pyridyl 0 4 153 6-methyl -Pyridin-2-yl 0 4 154 4,6 dimethyl-pyridin-2-yl 0 4 155 2-pyridyl 0 4 156 4-pyridyl 0 4 157 2-pyradinyl 0 4 -52- 5 15 20 200526611 j into Example 4 (synthesis of starting materials) α to 3 alcohols (1: 1 strokes), add ethyl xanthate potassium salt (32 g) and methyl fat fοr_ldlne (4 g of hydrochloride), and the mixture was slowly dropped into the sulfur solution dissolved in carbon disulfide, sulfur, and heated under reflux for 30 hours, at # & 4Λ〇ρ, > g 'Nuclear T The solvent was distilled off, and the residue was added with water (ml ml) and 6N 钠 sodium oxide aqueous solution (50 mm) = stirred for 10 minutes, insoluble matter was filtered off, and the filtrate was placed at room temperature for one day, Under ice-cooling, the acid-base value was adjusted by adding concentrated hydrochloric acid. ^ 'Valley, left ethyl acetate (1⑻ml) was extracted three times, and the organic layer was dried with sulfuric acid. After distillation, the residue was passed through a tube. Purification by column chromatography (eluent, ethyl acetate: hexane: 4), to give 5. · thiosulfanyldisial (1.25 g, yield 11%) as white crystals. Gold (synthesis of starting materials)

〇- (CH2) 5

• OH 1,5-pentanediol (55 6 g, 533.8 mmol) and triethylamine (61 g, 603 mmol) were dissolved in tetrahydrofuran (2 ⑽ml). P-chlorobenzyl chloride (46 · 7 g, 266.9 mmol) was added dropwise. After the addition was completed, the mixture was stirred at room temperature -53-200526611 for 2 hours. Water (15 ml) was added and extracted with toluene. After the mixture was washed with water, the formazan layer was dried over anhydrous sodium sulfate, and the residue was subjected to column chromatography (n-hexane: ethyl acetate = 1: 1) to obtain 丨 (p-chlorobenzyloxy) Dipentyl alcohol (58.89 g), nD20 = ΐ5212, yield 91%. Jincheng Example 6 (Synthesis of starting materials)

15

^ Grasshopper chlorine (54.82 g, 431.93 mmol) was dissolved in dichloromethane: (500 gross liters) 'at _600, it was dissolved in dichloromethane (contact. Shi Feng (37 · 5 g, 479.92 mmol) solution, and then dripped;; chloroform (80 ml) of M p-gas phenylhydrazone)-5-pentanol (58 ·: Li 2 ^ 9.96 millimolar) solution, stir for 15 minutes, drop in the solution "= chloramine (121.41 g, L2 mole) and stir for 5 minutes to warm it to: Γ water (500 ml ) 'Separate the dichloromethane layer and dichloromethane layer; place: after drying', the solvent is removed by evaporation under reduced pressure, and the residue is passed through a tube of 20 hexane, acid ethyl _2) to obtain 1 chlorobenzyl group ) ~ Risk PI grams), ηυ, η = 1 20 15220, yield 88%. (Synthesis of starting materials)

ίί C—〇— (ch2) 4ch = CF2 -54- 200526611 Dibromodifluoromethane (66.52 g, 317 mmol) was dissolved in tetrahydrofuran (300 gas liters) 'at -78. 0, dropwise Tri- (dimethylamino) phosphine (10; 3 πg, 634 millimoles) 'After the addition was complete, the reaction solution was stirred for 30 minutes and allowed to come back to room temperature. (Ml)-(p-chlorobenzene) ^ -Nylon (38.15 g, 158 5 mmol), the solution was added for 2 hours, the mixture was added to the milliliter of water, extracted with ethyl acetate, The layer was dried over anhydrous magnesium sulfate, and the residue was removed by evaporation under reduced pressure. The residue was subjected to column chromatography (n-hexane): Η p-gas phenoxy can be prepared_6,6_difluoro_5 · ^ D A) 1.5315, the yield is 83%. .11 g) η 20-(Synthesis of starting materials) H. (CH2) 4CH = CF2 15 20 〇 Alcohol ⑽ml) bu (p-chlorobenzyloxy ¥ difluoro ^^ Η 9 86 ^ h ' Cool S water ☆ liquid (4G ml) 'at 5 (Γ (: stir 1 ㈣, 2 (200 ml) and extract the mixture with ethyl acetate, wash with water to remove the residue = dry the layer with anhydrous sulfuric acid and dry it in Lili The solvent-based residue was removed and the residue was subjected to Shixue chromatographic chromatography (n-hexa divided by 0.jy85, yield 84%. Synthesis of starting materials) -55- 200526611 h3c-s (o) 2-〇- (ch2) 4ch = cf2 5-Dissolving L hydroxy-6,6-difluoro-5-hexene (22.14 g, 162.62 mmol) and ^ ethylamine (18 g, 178.89 mmol) in dichloride Methane (400 mL,) and 'under' cooling in a water bath, drop into a solution of methanesulfonyl chloride (20.48 g, 178.89 mmol), and stir at room temperature for 30 minutes, then add water (300 and The organic layer was cut out. After washing with water, the organic layer was dried over anhydrous magnesium sulfate φ 10 ^ & the solvent was distilled off under reduced pressure, and the residue was subjected to column chromatography (n-hexane: g) H purpose ^ 3 ·· 1) 'prepared 丨 _ 曱 sulfonyloxy-6,6-difluorohexene (27 · 43) n 2〇 = 1.421, yield 79%. -Poor Example 1 · Test against Rhizobial Nematode (Shi / 0 Oil Magic ^ Spp) (Soil 銶 15 Test) The injured active compound was mixed into 99 parts of pumice In order to make fine particles 20, the test agent prepared as described above was added to the soil contaminated by rhizobium nematodes, so that the concentration of the compound was 10ρριη. (1/5000 are), each planting about 20 tomato seeds (variety: Kurihara), planted in a greenhouse -56-200526611 after 4 weeks of cultivation, carefully remove the plant without harming the roots, nodule index and control The effect was evaluated as follows: Degree of damage 5 0: No nodules were formed (complete control group) 1: A few nodules were formed 2: Nodules were formed to a moderate degree 3: Nodules were formed to a significant degree 4: Nodules were formed to a strong degree (equivalent to not Treated control group) 〇Σ (degree of damage X number of individuals) nodule index = ------------------------------ ---------- 1 () 〇 Total number of individuals tested x 4 5 The control effect of the test compound can be evaluated according to the following equation: ( Nodule Index of Treatment Zone-Nodule Index of Treatment Zone) Effect of Control [%] = ------------------------------- ---------------------------- 100 Nodule Index of Untreated Zones For example, in the test described, the following compounds ) 1) 100% control effect at an effective concentration of 111. Compounds Nos. 4 and 5. -57- 25 200526611 Test example 2: Herbicidal activity (Ziyi, an anti-active compound formulation, soil weed treatment before weeding in the field) Vehicle: 5 parts by weight of acetone Emulsifier: benzyloxypolyethylene glycol _ 1 Formulations of parts by weight of active substance are made as emulsifiable concentrates, which are based on mixing parts by weight of active compound with the above-mentioned amounts of carrier and emulsifier, and the amount of the formulated formulation is then diluted with water. | 10 Test method In the greenhouse, the soil ring i on the surface of the spider (120 cm2) filled with pastoral soil is sown by Echinochha CruSgaUi, Setaria viridis,

Amaranthus retroflexus and Polygonum 穐 穐 and 15 on the soil 'the diluted solution of each active compound prepared according to the above method was evenly sprayed on the surface layer of each bowl' two weeks after the treatment, the effect of weed control was examined 0 results 20 Results 'For example' At a rate of 2 kg of active compound applied per hectare, compounds Nos. 5 and 6 showed more than 90% resistance to Bchinoc / ιοα crusgalli, Setaria viridis, Amaranthus retroflexus and herbicidal effects. -58- 200526611 Μ Example 3: Herbicidal activity (against field weed cotyledon germination post-treatment) Test method In a greenhouse, the surface soil 5 in a bowl (120 cm2) filled with pastoral soil 5 Xiangxiang 'Sowing Echinochloa crusgalli, Setaria viridis, Amaranthus retroflexus and p0fyg0num. After growing on the soil, ten days after sowing (at an average stage of 2 leaves), a solution of the active compound prepared in the same manner as in Test 2 above, averagely Spray the cotyledons of the plants in each bowl, and inspect the 10 effects of weeding three weeks after treatment. Results As a result, for example, at a rate of 2 kg of active compound per hectare, the compounds No. 6 and 86 showed more than 90% resistance and the herbicidal effects of 15 crusgalli, Setaria viridis, Amaranthus retroflexus. Formulation Example 1 f tear) To a mixture of 10 parts by weight of the compound of the present invention (No. 4) and 30 parts of bentonite (Meng 20 ex clay) and 58 parts of talc, 2 parts of lignin was added After fully kneading the sulfonate and 25 parts of water, use an extruder pelletizer to make 10-40 mesh sieve, and dry it at 40-5 (TC, to obtain the desired particle. (Particulate matter) • 59- 200526611 95 parts of submerged mineral particles (particle size distribution in the range of 0.2-2 millimeters in diameter) were placed in a rotary mixer, and 5 parts of the compound of the present invention (No. 4) were added under rotation. ), And sprayed together with the liquid diluent, uniformly wet, and then dried at 40-50 ° C to obtain the desired particles. Formulation Example 3 (emulsifiable concentrate) 30 parts by weight of the compound of the present invention (No. 4), 55 parts by weight of xylene, 8 parts by weight of polyoxyethylene alkylphenyl ether and 7 parts by weight of calcium alkylbenzenesulfonate, were mixed and stirred to form an emulsifiable concentrate. 10 Formulation example 4 (wettable powder) 15 parts by weight of the compound of the present invention (No. 5), 80 parts by weight of white carbon (aqueous amorphous silicon dioxide powder) Mixture with powdery clay (1: 5), 2 parts by weight of sodium alkylbenzene sulfonate and 3 parts by weight of sodium alkylnaphthalene sulfonate-formaldehyde-concentrate 15 are crushed together and mixed to wettability powder.

Claims (1)

200526611 X. Scope of patent application: i Compound of formula (I) 5 (I) where 10 R represents hydrogen, halogen, alkyl, cycloalkyl, alkoxyalkyl, alkylsulfanyl, sulfanyl, alkoxy, alkylthio, and optionally substituted benzene Or phenylfluorenyl, or represents a optionally substituted heteroaryl group having at least one heteroatom selected from NO and S, m represents 3, 4, 5, 6, 7, 8, 9, or 10, and n Represents 0, 1, or 2. 2. The compound of formula (I) according to item 1 of the scope of patent application, wherein 15 R represents hydrogen, chlorine, fluorine, bromine, Cw alkyl, C3-8-cycloalkyl, c2f alkoxyalkyl, Cw alkylsulfide Alkyl, chloro- or fluoro-substituted Cw alkyl, alkoxy, Cl-4-alkylthio, representing optionally halogen-, Ci-4-alkyl-, CM-alkoxy-, Cl -4 · Alkylthio ... CW newyl- or reader-substituted 2phenyl or benzyl, or optionally substituted halide-. -4? R-oxyl- or cl-4-i-alkyl-substituted heteroaryl groups having a straight heterogeneous m atom of N, ^ s represent 3, 4, 5, 6 9, or 10, and η represents 0 1 or 2 ° 20 200526611 3. The compound of formula (I) according to item 1 of the scope of patent application, wherein R represents hydrogen, chlorine, fluorine, bromine, alkyl, C3_6-cycloalkyl, C2_4 (total number of carbon atoms) ) -Alkoxyalkyl, c2_4 (total number of carbon atoms) -alkylsulfanyl, chloro- or fluoro-substituted Cw alkyl, Cu-alkoxy, 5 Cn Chlorine-'air ·-'> odor-'methyl-' fluorenyloxy-, methylthio, trifluoromethyl- or nitro-substituted phenyl or benzoyl ', or alternatively optionally bromine- Or fluorenyl-substituted furanyl, thienyl, pyridyl, pyrimidinyl, or pyrimiyl, _m represents 3, 4, 5, 6, 7, or 8, and η represents 0, 1, or 2. A method for preparing a compound of formula (I) according to item 1 of the scope of patent application, which comprises the following step (a) making the compound of formula (II) Where R is defined as defined in item 1 of the scope of the patent application, and 20 is reacted with a compound of formula (III) M-S02-0- (CH2) mCH = CF2 (III) where -62- 200526611 m is selected from the following Step, ', the definition in item 1, the compound of the formula KI S— (CH2) mCH = CF2 (| a) obtained by oxidation with an oxidizing agent 5. A pesticide composition comprising—or a plurality of items of item 1 Compounds of formula (I) and conventional applications x * Patent Scope 6. A method for controlling pests, which includes the compound of formula (1) with the formula Si: item 15 acting on a methyl group or P-methylbenzyl, and the definition is as in the scope of patent application R 7 · Use according to the scope of patent application scope! The use of one or more compounds of formula (I) in the control of pests. 8. A method for preparing a pesticide composition, comprising mixing one or more compounds of formula (I) according to item 1 of the scope of the patent application with a spreading agent and / or a surfactant and / or other adjuvants. -63- 200526611 VII. Designated Representative Map: (1) The designated representative map in this case is: (). (2) Brief description of the component symbols in this representative figure: None 8. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: ❿ S (〇) n (CH2) mCH = CF2 (0 -4-