WO 86/07590 discloses certain polyhaloalkene compounds with a nematicidal activity. U. S.

Patent No. 3,513, 172 also discloses certain trifluorobutenyl compounds with nematicidal activity.

GB 2 293 380 A discloses certain heterocyclic compounds with nematicidal activity. WO 95/04727 Al describes a process for preparing fluoroalkenylthioheterocyclic derivatives. WO 95/24403 Al also describes 4,4-difluorobutenyl compounds which are useful as nematicides.

Finally, WO 99/52874 Al discloses difluoroalkene derivatives which can be used for controlling animal pests. However, these compounds have not gained any particular importance to date.

There have now been found new difluoroalkenes represented by the following 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 having 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.

The compounds of formula (I) are very active against nematodes. The compounds of the formula (I) further show very good insecticidal and herbicidal activity.

In the definitions, the hydrocarbon chains, such as alkyl, are straight-chain or branched. Preferred substituents or preferred ranges of the radicals which are present in the formulae listed above and below are defined below.

Compounds of the above-rnentioned formula (I) can be synthesized, for example, by the following process (a) and by the following process (b).

Process (a) The novel substituted difluoroalkenes of the formula (1) wherein n represents 0 are obtained by reacting a compound of the formula (II)

wherein R is as defined above, with a compound of the formula (m) M-S02-0- (CH2) n, CH=CF2 (m) III) wherein M represents methyl or p-tolyl, and m is as defined above.

Process (b) The novel substituted difluoroalkenes of the formula (I) wherein n represents 1 or 2 are obtained by oxidizing a compound of the formula (Ia) wherein R and m are as defined above, with a suitable oxidizing agent.

In the present specification"halogen"preferably represents fluoro, chloro, bromo or iodo, and particularly preferably represents fluoro, chloro or bromo.

"Alkyl"preferably represents straight-chain or branched-chain Cl 12-alkyl, for example, methyl, ethyl, n-or iso-propyl, n-, iso-, sec-or tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-

decyl, n-undecyl, n-dodecyl, etc. , and particularly preferably represents methyl, ethyl, n-or iso- propyl, n-, iso-, sec-or tert-butyl, n-pentyl or n-hexyl.

"Cycloalkyl"preferably represents C38cycloalkyl, particularly preferably represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, or cyclooctyl, and very particularly preferably represents cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

The definition given above for"alkyl"can be equally applied to the alkyl moieties in "alkoxyalkyl","alkylthioalkyl","haloalkyl","alkoxy"and"alkyl thio".

"Heteroaryl"preferably represents a 5-or 6-membered heterocyclic group having at least one heteroatom, preferably 1-3 heteroatoms selected from N, O and S."Heteroaryl"particularly preferably represents a group selected from furyl, thienyl, pyridyl, pyrimidinyl and pyrazinyl.

According to the present invention compounds of the formula (I) are preferred wherein R represents hydrogen, chloro, fluoro, bromo, Cl 6-alkyl, C38-cycloalkyl, C26 (total carbon number)-alkoxyalkyl, C2-6 (total carbon number) -alkylthioalkyl, chloro-or fluoro- substituted C-alkyi, Ci -alkoxy, Ci -alkylthio, represents optionally halogen-, Cl4- alkyl-, C1-4-alkoxy-, C1-4alkylthio-, C1-4-haloalkyl-or nitro-substituted phenyl or benzyl, or represents optionally halogen-, C1-4alkyl-, C1-4alkoxy- or C1-4-haloalkyl-substituted 5-or 6-membered heteroaryl having 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.

According to the present invention compounds of the formula (I) are particularly preferred wherein R represents hydrogen, chloro, fluoro, bromo, C1-4alkyl, C3-6cycloalkyl, C2-4 (total carbon number) -alkoxyalkyl, C2-4 (total carbon number)-alkylthioalkyl, chloro-or fluoro- substituted C1-2alkyl, C1-3alkoxy, C1-3-alkylthio, represents optionally chloro-, fluoro-, bromo-, methyl-, methoxy-, methylthio-, trifluoromethyl-or nitro-substituted phenyl or benzyl, or represents optionally bromo-or methyl-substituted furyl, thienyl, pyridyl, pyrimidinyl or pyrazinyl, m represents 3,4, 5,6, 7 or 8, and n represents 0,1 or 2. Using, for example, 5-mercapto-1, 2, 4-thiadiazole and 1-methanesulfonyloxy-6, 6-difluoro-5-hexene as starting materials, the course of the reaction in the process (a) according to the invention can be illustrated by the following formula scheme:

N 'U CH=CF, c\ SH base fjtT : N S Using, for example, 5-(6, 6-difluoro-5-hexenylthio)-1, 2,4-thiadiazole and m-chloroperbenzoic acid, (oxidizing agent) as starting materials, the course of the reaction in the process (b) according to the invention can be illustrated by the following formula scheme: oxidation N NsS/ S S g SO The compounds of the formula (in), used as starting material in the aforementioned process (a), are mostly known compounds described in, for example, JP 01308270 A, WO 86/07590 Al and WO 95/24403 Al. The compounds of the formula (In can be easily obtained by known processes described in, for example, DE 4239727 Al, JP 60255782 A, JP 01308270 A, EP 0 534 219 Al, etc.

Specific examples for compounds of the formula (IT) are: 5-mercapto-1, 2,4-thiadiazole, 5-mercapto-3-methyl-1, 2,4-thiadiazole, 5-mercapto-3-tert-butyl-1, 2, 4-thiadiazole, 5-mercapto-3-methoxy-1,2, 4-thiadiazole, 5-mercapto-3-phenyl-1, 2,4-thiadiazole, 3-ethyl-5-mercapto-1,2, 4-thiadiazole, 5-mercapto-3-n-propyl-1, 2, 4-thiadiazole,

3-isopropyl-5-mercapto-1,2, 4-thiadiazole, 5-mercapto-3-n-butyl-1, 2,4-thiadiazole, 5-mercapto-3-sec-butyl-1, 2, 4-thiadiazole, 5-mercapto-3-n-pentyl-1, 2,4-thiadiazole, 3-cyclopropyl-5-mercapto-1, 2,4-thiadiazole, 3-cyclopentyl-5-mercapto-1, 2,4-thiadiazole, 3-cyclohexyl-5-mercapto-1, 2,4-thiadiazole, 5-mercapto-3-methoxyrnethyl-1, 2, 4-thiadiazole, 3-ethoxymethyl-5-mercapto-1, 2,4-thiadiazole, 3-isopropoxy-5-mercapto-1, 2, 4-thiadiazole, 5-mercapto-3-methylthiomethyl-1, 2, 4-thiadiazole, 3-ethylthiomethyl-5-mercapto-1,2, 4-thiadiazole, 3-isopropylthiomethyl-5-mercapto-1, 2,4-thiadiazole, 3-chloromethyl-5-mercapto-1, 2,4-thiadiazole, 3-(2-chloroethyl)-5-mercapto-1, 2, 4-thiadiazole, 3-trifluoromethyl-5-mercapto-1, 2,4-thiadiazole, 5-mercapto-3-pentafluoroethyl-1,2, 4-thiadiazole, 3-ethoxy-5-mercapto-1, 2,4-thiadiazole, 3-isopropoxy-5-mercapto-1, 2,4-thiadiazole, 5-mercapto-3-methylthio-1, 2,4-thiadiazole, 3-ethylthio-5-mercapto-1, 2,4-thiadiazole, 3-isopropylthio-5-mercapto-1, 2, 4-thiadiazole, 3-benzyl-5-mercapto-1, 2, 4-thiadiazole,

3- (4-fluorobenzyl)-5-mercapto-1, 2,4-thiadiazole, 3- (2-chlorobenzyl)-5-mercapto-1, 2, 4-thiadiazole, 3- (4-broniobenzyl)-5-mercapto-1, 2,4-thiadiazole, 5-mercapto-3- (3-trifluoromethylbenzyl)-1, 2,4-thiadiazole, 5-mercapto-3- (4-trifluoromethylbenzyl)-1, 2,4-thiadiazole, 5-mercapto-3- (4-methylbenzyl)-1, 2,4-thiadiazole, 5-mercapto-3-(4-methoxybenzyl)-1, 2,4-thiadiazole, 5-mercapto-3- (4-methylthiobenzyl)-1, 2,4-thiadiazole, 3-(2, 4-dichlorobenzyl)-5-mercapto-1, 2, 4-thiadiazole, 3-(2,4-dimethylbenzyl)-5-mercapto-1, 2,4-thiadiazole, 3-(2-fluorophenyl)-5-mercapto-1, 2, 4-thiadiazole, 3- (3-fluorophenyl)-5-mercapto-1, 2,4-thiadiazole, 3-(4-fluorophenyl)-5-mercapto-1, 2,4-thiadiazole, 3-(2-chlorophenyl)-5-mercapto-1, 2,4-thiadiazole, 3- (3-chlorophenyl)-5-mercapto-1, 2,4-thiadiazole, 3- (4-chlorophenyl)-5-mercapto-1, 2,4-thiadiazole, 3- (4-bromophenyl)-5-mercapto-1, 2,4-thiadiazole, 5-mercapto-3-(4-trifluoromethylphenyl)-1, 2,4-thiadiazole, 5-mercapto-3- (3-tolyl)-1, 2,4-thiadiazole, 5-mercapto-3- (4-tolyl)-1, 2,4-thiadiazole, 5-mercapto-3- (4-methoxyphenyl)-1, 2,4-thiadiazole, 5-mercapto-3- (4-methylthiophenyl)-1, 2, 4-thiadiazole, 3-(2,4-dichlorophenyl)-5-mercapto-1, 2, 4-thiadiazole,

3- (2, 4-dimethylphenyl)-5-mercapto-1, 2,4-thiadiazole, 3-bromo-5-mercapto-1, 2,4-thiadiazole, 3-(2-furyl)-5-mercapto-1, 2, 4-thiadiazole, 5-mercapto-3- (2-thienyl)-1, 2,4-thiadiazole, 5-mercapto-3- (3-thienyl)-1, 2,4-thiadiazole, 3- (5-bromothiophen-2-yl)-5-mercapto-1, 2,4-thiadiazole, 5-mercapto-3- (5-methylthiophen-2-yl)-1, 2,4-thiadiazole, 3- (4, 5-dibromothiophen-2-yl)-5-mercapto-1, 2,4-thiadiazole, 5-mercapto-3-(2-pyridyl)-1, 2, 4-thiadiazole, 5-merc apto-3- (3-pyridyl)-1, 2,4-thiadiazole, 5-mercapto-3-(4-pyridyl)-1, 2,4-thiadiazole, 5-mercapto-3-(6-methylpyridin-2-yl)-1, 2, 4-thiadiazole, 3- (4, 6-dimethyl-pyridin-2-yl)-5-mercapto-1, 2,4-thiadiazole, 5-mercapto-3-(2-pyrimidinyl)-1, 2,4-thiadiazole, 5-mercapto-3- (4-pyrimidinyl)-1, 2,4-thiadiazole, 5-mercapto-3-(2-pyrazinyl)-1, 2,4-thiadiazole.

Specific examples for compounds of the formula (in) are known compounds described in JP 11349557 A.

Specific examples for the compounds of the formula (III) are, for example: 1-methanesulfonyloxy-5, 5-difluoro-4-pentene, 1-methanesulfonyloxy-6, 6-difluoro-5-hexene, 1-methanesulfonyloxy-7, 7-difluoro-6-heptene, 1-methanesulfonyloxy-8, 8-difluoro-7-octene,

1-methanesulfonyloxy-9, 9-difluoro-8-nonene, <BR> <BR> <BR> <BR> <BR> <BR> 1-methanesulfonyloxy-10, 10-difluoro-9-decene, <BR> <BR> <BR> <BR> <BR> <BR> <BR> <BR> 1-methanesulfonyloxy-11, 11-difluoro-10-undecene, 1-methanesulfonyloxy-12, 12-difluoro-11-dodecene, etc.

The compounds of the formula (Ia), used as starting material in the aforementioned process (b), correspond to the compounds of the formula (1) wherein n represents 0. They cam be prepared according to the aforementioned process (a).

Suitable oxidizing agents for the oxidation of the compounds of the above-mentioned formula (Ia) in process (b), are, in general, those used usually in the field of organic chemistry, for example, hydrogen peroxide solution, m-chloroperbenzoic acid, peracetic acid, perbenzoic acid, magnesium monoperoxyphthalate or potassium peroxymonosulfate.

The reaction of the aforementioned process (a) can be conducted in the presence of an appropriate diluent. Suitable diluents are, for example, aliphatic, alicyclic and aromatic hydrocarbons, for example, hexane, cyclohexane, petroleum ether, ligroine, benzene, toluene, xylene, etc.; ethers, for example, diethyl ether, methyl ethyl ether, di-isopropyl ether, dibutyl ether, dioxane, tetrahydrofuran, etc.; ketones, for example, acetone, methyl ethyl ketone, methyl isobutyl ketone, etc.; nitriles, for example, acetonitrile, propionitrile, acrylonitrile, etc.; acid amides, for example, dimethylformamide, dimethylacetamide, N-methylpyrrolidone, etc.

The reaction can be conducted in the presence of an acid binder. Suitable acid binders are, for example, hydroxides, carbonates and alcoholates, etc. of alkali metals and tertiary amines, for example, triethylamine, diethylaniline, pyridine, 4-dimethylaminopyridine, 1,4-diazabicycle- [2,2, 2] octane (DABCO), 1, 8-diazabicyclo [5, 4, 0] undec-7-ene (DBU), etc.

When carrying out the process (a) according to the invention, the reaction temperatures can be varied within a relatively wide range. In general, the process is carried out at temperatures between 0°C and 180°C, preferably between 20°C and 120°C.

Process (a) according to the invention is generally carried out under atmospheric pressure.

However, it is also possible to carry out the process according to the invention under elevated or reduced pressure, in general between 0.1 bar and 10 bar.

The compounds of the formula (1) of the present invention can be obtained, for example, by reacting 0.7-1. 2 moles of a compound of the formula (with 1 mole of a compound of the

formula (II) in a diluent, for example, acetonitrile, in the presence of 0.9-1. 1 moles of an acid binder, for example, potassium carbonate, under reflux.

The reaction of the aforementioned preparation process (b) can be conducted in the presence of an appropriate diluent. Suitable diluents are, for example, aliphatic, alicyclic and aromatic hydrocarbons (may be optionally chlorinated), for example, hexane, cyclohexane, petroleum ether, ligroine, benzene, toluene, xylene, methylene chloride, chloroform, carbon tetrachloride, ethylene chloride, chlorobenzene, etc. ; ethers, for example, diethyl ether, methyl ethyl ether, di-isopropyl ether, dibutyl ether, dioxane, tetrahydrofuran, etc. ; alcohols, for example, methanol, ethanol, isopropanol, butanol, ethylene glycol, etc. ; esters, for example, ethyl acetate, amyl acetate, etc. ; acid amides, for example, dimethylformamide, dimethylacetamide, N-methylpyrrolidone, etc.; carboxylic acids, for example, formic acid, acetic acids, etc.

When carrying out the process (b) according to the invention, the reaction temperatures can be varied within a relatively wide range. In general, the process is carried out at temperatures between - 20°C and 100°C, preferably between 0°C and 80°C.

Process (b) according to the invention is generally carried out under atmospheric pressure.

However, it is also possible to carry out the process according to the invention under elevated or reduced pressure, in general between 0.1 bar and 10 bar.

In conducting the process (b), the objective compound of the corresponding formula (I) can be obtained, for example, by reacting 0.8-3 moles of m-chloroperacetic acid with 1 mole of a compound of a formula (Ia) in a diluent, for example, methylene chloride, at room temperature.

The compounds of the formula (I) of the present invention show strong nematicidal and herbicidal activity. They are also active against insects. They can, therefore, be used effectively as nematicides and herbicides in the field of, for example, agriculture and forestry, but also as nematicides and/or anti-parasitic agents in the field of animal health. Furthermore, the compounds of the formula (I) of the present invention show low phytotoxicity with regard to crops. In the present specification"harmful organism"means animals and plants that are harmful to crops or animals, including harmful nematodes, insects and weeds.

The compounds according to the invention can be used with particularly good results for controlling plant-damaging nematodes, such as, for example, Meloidogyne incognita larvae, for controlling plant-damaging insects, such as, for example, the peach aphid (Myzus persicae), the larvae of the mustard beetle (Phaedon cochleariae), against the caterpillars of the army worm

(Spodoptera frugiperda), and also for controlling plant-damaging spider mites (Tetraraychus urticae).

The plant-parasitic nematodes include, for example, Pratylenchus spp. , Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp. , Globodera spp. , Meloidogyne spp. , Aphelenchoides spp. , Longidorus spp. , Xiphinema spp. , Trichodorus spp. and Bursaphelenchus spp. They are, however, not restricted to these.

At certain concentrations or application rates, the compounds according to the invention may, if appropriate, also be used as herbicides. The compounds according to the present invention can be used to control, for example, the following weeds: Genera of the dicotyledonous weeds: Sinapis, Leipidium, Galium, Stellaria, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Ipomoea, Polygonum, Ambrosia, Cirsium, Sonchus, Solanum, Rorippa, Lamium, Veronica, Datura, Viola, Galeopsis, Papaver, Centaurea, Galinsoga, Rotala, Lindernia, etc.

Genera of the monocotyledonous weeds: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Agrostis, Alopecurus, Cynodon, etc.

The use of the compounds of the present invention, however, is not restricted to the above- mentioned plants. The compounds of the present invention act as non-selective or selective herbicides depending upon the application concentration and can be used at wither stages before and after germination.

All plants and plant parts can be treated in accordance with the invention. Plants are to be understood as meaning in the present context all plants and plant populations such as desired and undesired wild plants or crop plants (inclusive of naturally occurring crop plants). Crop plants can be plants which can be obtained by conventional plant breeding and optimization methods or by biotechnological and recombinant methods or by combinations of these methods, inclusive of the transgenic plants and inclusive of the plant cultivars protectable or not protectable by plant breeders'rights. Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as shoot, leaf, flower and root, examples which may be mentioned being leaves, needles, stalks, stems, flowers, fruit bodies, fruits, seeds, roots, tubers and rhizomes. The plant parts also include harvested material, and vegetative and generative propagation material, for

example cuttings, tubers, rhizomes, offsets and especially seeds. The compounds can, for example, be used for coating seeds to protect them from pests.

As already mentioned above, it is possible to treat all plants and their parts according to the invention. In a preferred embodiment, wild plant species and plant cultivars, or those obtained by conventional biological breeding, such as crossing or protoplast fusion, and parts thereof, are treated. In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated. The terms"parts"or"parts of plants"or"plant parts"have been explained above.

The active compounds according to the invention can be present in their commercially available formulations and in the use forms, prepared from these formulations, as a mixture with other active compounds, such as insecticides, attractants, sterilizing agents, bactericides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides. The insecticides include, for example, phosphoric acid esters, carbamates, carboxylates, chlorinated hydrocarbons, phenylureas and substances produced by microorganisms, inter alia.

Further, the active compounds of the present invention can be used also in a mixture with a synergist.

Such formulations and application forms can be mentioned as being commercially especially useful.

Said synergist itself must not be active itself, but is a compound that enhances the action of the active compound.

The content of the active compounds of the present invention in a commercially useful formulation or application form can be varied in a wide range. The active-compound content of the use forms prepared from the commercial formulations can vary within wide limits. The active-compound concentration of the use forms can be from 0.0000001 to 100 % by weight of active compound, preferably between 0.0001 and 1 % by weight. The application rate can also be varied in a wide range. Preferably it is within a range of about 0.05 to 4 kg, preferably about 0.1 to 2 kg of the active compound per hectare.

Examples of advantageous mixing components are, for example, the following: Fungicides aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilazine, azaconazole, azoxystrobin, benalaxyl, benodanil, benomyl, benzamacril, benzamacril-isobutyl, bialaphos, binapacryl, biphenyl, bitertanol, blasticidin-S, bromuconazole, bupirimate, buthiobate, calcium polysulphide, capsimycin, captafol, captan, carbendazim, carboxin, carvon, quinomethionate, chlobenthiazone, chlorfenazole,

chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon, cufraneb, cymoxanil, cyproconazole, cyprodinil, cyprofuram, debacarb, dichlorophen, diclobutrazole, diclofluanid, diclomezine, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dithianon, dodemorph, dodine, drazoxolon, ediphenphos, epoxiconazole, etaconazole, ethirimol, etridiazole, famoxadon, fenapanil, fenarimol, fenbuconazole, fenfuram, fenitropan, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, flumetover, fluoromide, fluquinconazole, flurprimidol, flusilazole, flusulfamide, flutolanil, flutriafol, folpet, fosetyl-aluminium, fosetyl-sodium, fthalide, fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole, furconazole-cis, furmecyclox, guazatine, hexachlorobenzene, hexaconazole, hymexazole, imazalil, imibenconazole, iminoctadine, iminoctadine albesilate, iminoctadine triacetate, iodocarb, ipconazole, iprobenfos (IBP), iprodione, irumamycin, isoprothiolane, isovaledione, kasugamycin, kresoxim-methyl, copper preparations, such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulphate, copper oxide, oxine- copper and Bordeaux mixture, mancopper, mancozeb, maneb, meferimzone, mepanipyrim, mepronil, metalaxyl, metconazole, methasulfocarb, methfuroxam, metiram, metomeclam, metsulfovax, mildiomycin, myclobutanil, myclozolin, nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol, ofurace, oxadixyl, oxamocarb, oxolinic acid, oxycarboxim, oxyfenthiin, paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen, pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz, procymidone, propamocarb, propanosine-sodium, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilon, pyroxyfur, quinconazole, quintozene (PCNB), sulphur and sulphur preparations, tebuconazole, tecloftalam, tecnazene, tetcyclacis, tetraconazole, thiabendazole, thicyofen, thifluzamide, thiophanate-methyl, thiram, tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triazbutil, triazoxide, trichlamide, tricyclazole, tridemorph, triflumizole, triforine, triticonazole, uniconazole, validamycin A, vinclozolin, viniconazole, zarilamide, zineb, ziram and also Dagger G, OK-8705, OK-8801, α-(1,1-dimethylethyl)-#-(2- phenoxyethyl)-1 H-1, 2, 4-triazole-1-ethanol, a-(2, 4-dichlorophenyl)-ß-fluoro-b-propyl-1 H-1, 2, 4-tri- azole-1-ethanol, a-(2, 4-dichlorophenyl)-ß-methoxy-a-methyl-lH-1, 2, 4-triazole-1-ethanol, a-(5- methyl-1, 3-dioxan-5-yl)-ß-[[4-(trifluoromethyl)-phenyl]-methylene]-l H-1, 2, 4-triazole-l-ethanol, (5RS, 6RS) -6-hydroxy-2, 2,7, 7-tetramethyl-5-(1H-1, 2, 4-triazol-1-yl)-3-octanone, (E)-a- (methoxy- imino)-N-methyl-2-phenoxy-phenylacetamide, isopropyl 1- {2-methyl-1- [ [ [1- (4-methylphenyl)-ethyl]- amino]-carbonyl]-propyl}-carbamate, 1-(2,4-dichlorophenyl)-2-(1H-1, 2, 4-triazol-1-yl)-ethanone O- (phenylmethyl) oxime, 1-(2-methyl-1-naphthalenyl)-1H-pyrrol-2, 5-dione, 1- (3, 5-dichlorophenyl) -3- (2-propenyl) -2, 5-pyrrolidinedione, 1-[(diiodomethyl)-sulphonyl]-4-methyl-benzene, 1-[[2-(2, 4- <BR> <BR> <BR> dichlorophenyl)-1, 3-dioxolan-2-yl]-methyl]-lH-imidazole, l- [ [2- (4-chlorophenyl)-3-phenyloxiranyl]- methyl]-1H-1, 2,4-triazole, l- [l- [2- [ (2, 4-dichloropheny !)-methoxy]-phenyl]-ethenyI]-lH-imidazole, 1- methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinole, 2', 6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-

trifluoro-methyl-1, 3-thiazole-5-carboxanilide, 2, 2-dichloro-N- [l- (4-chlorophenyl)-ethyl]-l-ethyl-3- methyl-cyclopropanecarboxamide, 2, 6-dichloro-5- 4-pyrimidinyl thiocyanate, 2,6- dichloro-N- (4-trifluoromethylbenzyl)-benzamide, 2, 6-dichloro-N-[[4-(trifluoromethyl)-phenyl]- methyl] -benzamide, 2- (2, 3,3-triiodo-2-propenyl)-2H-tetrazole, 2-[(1-methylethyl)-sulphonyl]-5- (trichloromethyl) -1, 3,4-thiadiazole, 2-[[6-deoxy4-0-(4-O-methyl-ß-D-glycopyranosyl)-a-D- glucopyranosyl]-amino]-4-methoxy-lH-pyrrolo [2, 3-d] pyrimidine-5-carbonitrile, 2-aminobutane, 2- <BR> <BR> <BR> <BR> bromo-2- (bromomethyl)-pentanedinitrile, 2-chloro-N- (2, 3-dihydro-1, 1, 3-trimethyl-lH-inden-4-yl)-3- pyridinecarboxamide, 2-chloro-N-(2,6-dimethylphenyl)-N-(isothiocyanatomethyl)-ace tamide, 2- phenylphenol (OPP), 3, 4-dichloro-l- [4- (difluoromethoxy)-phenyl]-lH-pyrrol-2, 5-dione, 3,5-dichloro- <BR> <BR> <BR> <BR> N-[cyano-[(l-methyl-2-propynyl)-oxy]-methyl]-benzamide, 3-(1, 1-dimethylpropyl-l-oxo-lH-indene- 2-carbonitrile, 3- [2- (4-chlorophenyl)-5-ethoxy-3-isoxazolidinyl]-pyridine, 4-chloro-2-cyano-N, N- <BR> <BR> <BR> <BR> dimethyl-5- (4-methylphenyl)-lH-imidazole-1-sulphonamide, 4-methyl-tetrazolo [1, 5-a] quinazolin- 5 (4H)-one, 8- (1, 1-dimethylethyl)-N-ethyl-N-propyl-1, 4-dioxaspiro [4.5] decane-2-methanamine, 8- hydroxyquinoline sulphate, 9H-xanthene-2-[(phenylamino)-carbonyl]-9-carboxylic hydrazide, bis-(1- methylethyl) 3-methyl-4- [ (3-methylbenzoyl)-oxy]-2, 5-thiophenedicarboxylate, cis-1-(4- chlorophenyl)-2- (lH-1, 2,4-triazol-1-yl)-cycloheptanol, cis-4- [3- [4- (1, 1-dimethylpropyl)-phenyl-2- methylpropyl] -2, 6-dimethyl-morpholine hydrochloride, ethyl [ (4-chlorophenyl)-azo]-cyanoacetate, potassium hydrogen carbonate, methanetetrathiol sodium salt, methyl 1- (2, 3-dihydro-2,2-dimethyl- lH-inden-l-yl)-lH-imidazole-5-carboxylate, methyl N- (2, 6-dimethylphenyl)-N- (5- isoxazolylcarbonyl)-DL-alaninate, methyl N- (chloroacetyl)-N- (2, 6-dimethylphenyl) -DL-alaninate, N- (2, 3-dichloro-4-hydroxyphenyl)-1-methyl-cyclohexanecarboxamide, N- (2, 6-dimethylphenyl) -2- methoxy-N- (tetrahydro-2-oxo-3-furanyl)-acetamide, N- (2, 6-dimethylphenyl) -2-methoxy-N- <BR> <BR> <BR> <BR> (tetrahydro-2-oxo-3-thienyl)-acetamide, N- (2-chloro-4-nitrophenyl)-4-methyl-3-nitro-benzenesul- phonamide, N- (4-cyclohexylphenyl)-1, 4,5, 6-tetrahydro-2-pyrimidineamine, N- (4-hexylphenyl)- 1, 4,5, 6-tetrahydro-2-pyrimidineamine, N- (5-chloro-2-methylphenyl)-2-methoxy-N- (2-oxo-3- oxazolidinyl)-acetamide, N- (6-methoxy)-3-pyridinyl)-cyclopropanecarboxamide, N- [2, 2,2-trichloro- l- [ (chloroacetyl)-amino]-ethyl]-benzamide, N- [3-chloro-4, 5-bis (2-propinyloxy)-phenyl]-N'-methoxy- methanimidamide, N-formyl-N-hydroxy-DL-alanine-sodium salt, O, 0-diethyl [2- (dipropylamino)-2- oxoethyl]-ethylphosphoramidothioate, O-methyl S-phenyl phenylpropylphosphoramidothioate, S- methyl 1, 2, 3-benzothiadiazole-7-carbothioate, spiro [2H]-l-benzopyran-2, 1' (3'H)-isobenzofuran]-3'- one.

Bactericides bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin, probenazole, streptomycin, tecloftalam, copper sulphate and other copper preparations.

Insecticides/acaricide/nematicides abamectin, acephate, acetamiprid, acrinathrin, alanycarb, aldicarb, aldoxycarb, alpha-cypermethrin, alphamethrin, amitraz, avermectin, AZ 60541, azadirachtin, azamethiphos, azinphos A, azinphos M, azocyclotin, Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillus thuringiensis, baculo- viruses, Beauveria bassiana, Beauveria tenella, benclothiaz, bendiocarb, benfuracarb, bensultap, benzoximate, betacyfluthrin, bifenazate, bifenthrin, bioethanomethrin, biopermethrin, BPMC, bromophos A, buiencarb, buprofezin, butathiofos, butocarboxim, butylpyridaben, cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap, chloethocarb, chlorethoxyfos, chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M, chlovaporthrin, cis-resmethrin, cispermethrin, clocythrin, cloethocarb, clofentezine, cyanophos, cycloprene, cycloprothrin, cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyromazine, deltamethrin, demeton M, demeton S, demeton-S-methyl, diafenthiuron, diazinon, dichlorvos, diflubenzuron, dimefluthrin, dimethoat, dimethylvinphos, diofenolan, disulfoton, docusat-sodium, dofenapyn, eflusilanate, emamectin, empenthrin, endosulfan, Entomopfthora spp. , esfenvalerate, ethiofencarb, ethion, ethoprophos, etofenprox, etoxazole, etrimfos, fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenothiocarb, fenoxacrim, fenoxycarb, fenpropathrin, fenpyrad, fenpyrithrin, fenpyroximate, fenvalerate, fipronil, fluazinam, fluazuron, flubrocythrinate, flucycloxuron, flucythrinate, flufenoxuron, flutenzine, fluvalinate, fonophos, fosmethilan, fosthiazate, fubfenprox, furathiocarb, gamma-cyhalothrin, granulosis viruses, halofenozide, HCH, heptenophos, hexaflumuron, hexythiazox, hydroprene, imidacloprid, isazofos, isofenphos, isoxathion, ivermectin, nuclear polyhedrosis viruses, lambda-cyhalothrin, lufenuron, malathion, mecarbam, metaldehyde, methamidophos, Metharhizium anisopliae, Metharhizium flavoviride, methidathion, methiocarb, methyl, methoxyfenozide, metofluthrin, metolcarb, metoxadiazone, mevinphos, milbemectin, monocrotophos, naled, nitenpyram, nithiazine, novaluron, omethoat, oxamyl, oxydemethon M, Paecilomyces fumosoroseus, parathion A, parathion M, permethrin, phenthoat, phorat, phosalone, phosmet, phosphamidon, phoxim, pirimicarb, pirimiphos A, pirimiphos M, profenofos, potassium oleate, prallethrin, profluthrin, promecarb, propoxur, prothiofos, protlioat, pymetrozine, pyraclofos, pyresmethrin, pyrethrum, pyridaben, pyridathion, pyrimidifen, pyriproxyfen, quinalphos, ribavirin, salithion, sebufos, silafluofen, spinosad, sulfotep, sulprofos, tau-fluvalinate, tebufenozide, tebufenpyrad, tebupirimiphos, teflubenzuron, tefluthrin, temephos, temivinphos, terbufos, tetrachlorvinphos, theta-cypermethrin, thiamethoxam, thiapronil, thiatriphos, thiocyclam hydrogen oxalate, thiodicarb, thiofanox, thuringiensin, tralocythrin, tralomethrin, triarathene, triazamate, triazophos, triazuron, trichlophenidine, trichlorfon, Trichoderma atroviride, triflumuron, trimethacarb, vamidothion, vaniliprole, Verticillium lecanii, YI 5302, zeta-cypermethrin, zolaprofos, (lR-cis)- [5- (phenylmethyl)-3-furanyl]-methyl 3- [ (dihydro-2-oxo-3 (2H) -furanylidene)-methyl]-2, 2- dimethylcyclopropanecarboxylate, (3-phenoxyphenyl)-methyl 2,2, 3,3-tetramethyl-

cyclopropanecarboxylate, 1-[(2-chloro-5-thiazolyl) methyl] tetrahydro-3, 5-dimethyl-N-nitro-1, 3,5- triazine-2 (1H)-imine, 2-(2-chloro-6-fluorophenyl)-4-[4-(1,1-dimethylethyl) phenyl] -4, 5-dihydro- oxazole, 2- (acetlyoxy)-3-dodecyl-1, 4-naphthalenedione, 2-chloro-N- [ [ [4- (l-phenylethoxy)-phenyl]- amino]-carbonyl]-benzamide, 2-chloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)-phenyl]-am ino]- carbonyl] -benzamide, 3-methylphenyl propylcarbamate, 4-[4-(4-ethoxyphenyl)-4-methylpentyl]-1- fluoro-2-phenoxy-benzene, 4-chloro-2-(1,1-dimethylethyl)-5-[[2-(2, 6-dimethyl-4-phenoxyphenoxy) - ethyl] thio]-3 (2H)-pyridazinone, 4-chloro-2-(2-chloro-2-methylpropyl)-5-[(6-iodo-3-pyridinyl) - methoxy-3 (2H) -pyridazinone, 4-chloro-5-[(6-chloro-3-pyridinyl)methoxy]-2-(3, 4-dichlorophenyl) - 3 (2H)-pyridazinone, Bacillus thuringiensis strain EG-2348, [2-benzoyl-1-(1,1-dimethylethyl)- hydrazinobenzoic acid, 2, 2-dimethyl-3-(2, 4-dichlorophenyl)-2-oxo-1-oxaspiro [4.5] dec-3-en-4-yl butanoate, [3-[(6-chloro-3-pyridinyl) methyl]-2-thiazolidinylidene]-cyanamide, dihydro-2-(nitro- methylene)-2H-1, 3-thiazine-3 (4H) -carboxaldehyde, ethyl [2- [ [1, 6-dihydro-6-oxo-1- (phenylmethyl)-4- pyridazinyl] oxy] ethyl]-carbamate, N- (3, 4, 4-trifluoro-1-oxo-3-butenyl)-glycine, N- (4-chlorophenyl)-3- [4- (difluoromethoxy) phenyl] -4, 5-dihydro-4-phenyl-lH-pyrazole-l-carboxamide, N- [ (2-chloro-5- thiazolyl) methyl]-N'-methyl-N"-nitro-guanidine, N-methyl-N'-1(1-methyl-2-propenyl)-1, 2- hydrazinedicarbothioamide, N-methyl-N'-2-propenyl-1, 2-hydrazinedicarbothioamide, O, 0-diethyl [2- (dipropylamino)-2-oxoethyl]-ethylphosphoroamidothioate.

The active compounds of the present invention can be converted into customary formulations which can be used in the field of crop protection, such as solutions, emulsions, wettable powders, water-dispersible granules, suspensions, powders, foaming agents, pastes, granules, active compound-impregnated natural and synthetic substances, microcapsules, fumigants etc.

These formulations can be prepared according to per se known methods, for example, by mixing the active compounds with extenders, namely liquid, liquefied gas or solid diluents or carriers, and optionally with surface-active agents, namely emulsifiers and/or dispersants and/or foam-forming agents. If the extender used is water, it is also possible to use, for example, organic solvents as auxiliary solvents. Suitable liquid solvents are essentially: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chloro- benzene, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example mineral oil fractions, mineral or vegetable oil, alcohols, such as butanol or glycol, and also their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, and also water.

Liquid diluents or carriers can be, for example, aromatic hydrocarbons (for example, xylene, toluene, alkylnaphthalene etc. ), chlorinated aromatic or chlorinated aliphatic hydrocarbons (for

example, chlorobenzenes, ethylene chlorides, methylene chloride etc. ), aliphatic hydrocarbons (for example, cyclohexane etc. or paraffins, such as, mineral oil fractions etc. ), alcohols (for example, butanol, glycols and their ethers, esters etc. ), ketones (for example, acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone etc. ), strongly polar solvents (for example, dimethylformamide, dimethyl sulfoxide etc. ), water etc.

Liquefied gas diluents or carriers are liquefied substances which are gases at normal temperature and pressure. Liquefied gas diluents can be, for example, aerosol propellants such as butane, propane, nitrogen gas, carbon dioxide, halogenated hydrocarbons, etc.

Solid diluents can be, for example, ground natural minerals (for example, kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite, diatomaceous earth etc. ), ground synthetic minerals (for example, highly dispersed silicic acid, alumina, silicates etc. ) etc.

Solid carriers for granules can be, for example, crushed and fractionated rocks (for example, calcite, marble, pumice, sepiolite, dolomite etc. ) synthetic granules of inorganic and organic meals, particles of organic materials (for example, saw dust, coconut shells, maize cobs, tobacco stalks etc. ) etc.

Emulsifiers and/or foam-forming agents can be, for example, nonionic and anionic emulsifiers, for example, polyoxyethylene fatty acid esters, polyoxyethylene fatty acid alcohol ethers, such as, alkylaryl polyglycol ethers, alkylsulfonates, alkylsulfates, arylsulfonates etc. , albumin hydrolysis products etc.

Dispersants include, for example, lignin sulfite waste liquor, methyl cellulose etc.

Tackifiers can also be used in formulations (powders, granules, emulsifiable concentrates). As usable tackifiers there can be mentioned, for example, carboxymethyl cellulose, natural and synthetic polymers (for example, gum Arabic, polyvinyl alcohol, polyvinyl acetate etc.).

Colorants can also be used. Colorants can be, for example, inorganic pigments (for example, iron oxide, titanium oxide, Prussian Blue etc, ), organic dyestuffs such as alizarin dyestuffs, azo dyestuffs or metal phthalocyanine dyestuffs, and further traces nutrients such as salts of metals such as iron, manganese, boron, copper, cobalt, molybdenum, zinc etc.

Said formulations can contain the aforementioned active components in a range of generally 0.1-95 % by weight, preferably 0.5-90 % by weight.

The preparation and possible application forms of the compounds of the present invention will be described more specifically by the following examples.

The active compounds according to the invention act not only against plant pests, but also in the veterinary medicine sector against animal parasites (ectoparasites), such as hard ticks, soft ticks, mange mites, leaf mites, flies (biting and licking), parasitic fly larvae, lice, hair lice, feather lice and fleas. These parasites include: From the order of the Anoplurida, for example, Haematopinus spp. , Linognathus spp. , Pediculus spp. , Phtirus spp. and Solenopotes spp. From the order of the Mallophagida and the suborders Amblycerina and Ischnocerina, for example, Trimenopon spp. , Menopon spp. , Trinoton spp., Bovicola spp., Werneckiella spp. , Lepikentron spp. , Damalina spp. , Trichodectes spp. and Felicola spp. From the order Diptera and the suborders Nematocerina and Brachycerina, for example, Aedes spp., Anopheles spp. , Culex spp. , Simulium spp. , Eusimulium spp. , Phlebotomus spp., Lutzomyia spp. , Culicoides spp. , Chrysops spp. , Hybomitra spp. , Atylotus spp. , Tabanus spp., Haematopota spp. , Philipomyia spp. , Braula spp. , Musca spp. , Hydrotaea spp. , Stomoxys spp., Haematobia spp. , Morellia spp. , Fannia spp. , Glossina spp. , Calliphora spp. , Lucilia spp., Chrysomyia spp., Wohlfahrtia spp. , Sarcophaga spp., Oestrus spp., Hypoderma spp. , Gasterophilus spp. , Hippobosca spp. , Lipoptena spp. and Melophagus spp. From the order of the Siphonapterida, for example, Pulex spp. , Ctenocephalides spp. , Xenopsylla spp. and Ceratophyllus spp. From the order of the Heteropterida, for example, Cimex spp. , Triatoma spp., Rhodnius spp. and Panstrongylus spp. From the order of the Blattarida, for example, Blatta orientalis, Periplaneta americana, Blattela germanica and Supella spp. From the subclass of the Acaria (Acarida) and the orders of the Meta-and Mesostigmata, for example, Argas spp., Ornithodorus spp. , Otobius spp., Ixodes spp. , Amblyomma spp. , Boophilus spp., Dermacentor spp. , Haemophysalis spp., Hyalomma spp. , Rhipicephalus spp. , Dermanyssus spp. , Raillietia spp. , Pneumonyssus spp., Sternostoma spp. and Varroa spp. From the order of the Actinedida (Prostigmata) and Acaridida (Astigmata), for example, Acarapis spp. , Cheyletiella spp., Ornithocheyletia spp. , Myobia spp. , Psorergates spp., Demodex spp. , Trombicula spp. , Listrophorus spp. , Acarus spp. , Tyrophagus spp. , Caloglyphus spp. , Hypodectes spp., Pterolichus spp. , Psoroptes spp. , Chorioptes spp. , Otodectes spp. , Sarcoptes spp. , Notoedres spp., Knemidocoptes spp. , Cytodites spp. and Laminosioptes spp.

The active compounds of the formula (I) according to the invention are also suitable for controlling arthropods which infest agricultural productive livestock, such as, for example, cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese and bees, other pets, such as, for example, dogs, cats, caged birds and aquarium fish, and also so-called test animals, such as, for example, hamsters, guinea pigs, rats and mice. By controlling these arthropods, cases of death and reduction in productivity (for meat, milk, wool, hides, eggs, honey etc. ) should be diminished, so that more economic and easier animal husbandry is possible by use of the active compounds according to the invention.

The active compounds according to the invention are used in the veterinary sector in a known manner by enteral administration in the form of, for example, tablets, capsules, potions, drenches, granules, pastes, boluses, the feed-through process and suppositories, by parenteral administration, such as, for example, by injection (intramuscular, subcutaneous, intravenous, intraperitoneal and the like), implants, by nasal administration, by dermal use in the form, for example, of dipping or bathing, spraying, pouring on and spotting on, washing and powdering, and also with the aid of moulded articles containing the active compound, such as collars, ear marks, tail marks, limb bands, halters, marking devices and the like.

When used for cattle, poultry, pets and the like, the active compounds of the formula (I) can be used as formulations (for example powders, emulsions, free-flowing compositions), which comprise the active compounds in an amount of 1 to 80% by weight, directly or after 100 to 10 000-fold dilution, or they can be used as a chemical bath.

The agents according to the invention are suitable for controlling pathogenic endoparasites encountered in humans and in animal husbandry and livestock breeding, in productive livestock, breeding stock, zoo animals, laboratory animals, animals used in experiments, and pets, and have low toxicity towards warm-blooded animals. They are active against all or some stages of development of the pests and against resistant and normally sensitive species. By controlling the pathogenic endoparasites, it is intended to reduce disease, mortality and decreasing performance (for example in the production of meat, milk, wool, hides, eggs, honey, etc. ), so that more economical and simpler animal keeping is possible by using the active compounds. The pathogenic endoparasites include cestodes, trematodes, nematodes and acantocephales, in particular: From the order of the Pseudophyllidea, for example Diphyllobothrium spp. , Spirometra spp., Schistocephalus spp. , Ligula spp. , Bothridium spp. , Diphlogonoporus spp. From the order of the Cyclophyllidea, for example Mesocestoides spp. , Anoplocephala spp. , Paranoplocephala spp., Moniezia spp. , Thysanosomsa spp. , Thysaniezia spp. , Avitellina spp. , Stilesia spp., Cittotaenia spp. , Andyra spp. , Bertiella spp. , Taenia spp. , Echinococcus spp. , Hydatigera spp. , Davainea spp., Raillietina spp. , Hymenolepis spp. , Echinolepis spp. , Echinocotyle spp. , Diorchis spp. , Dipylidium spp. , Joyeuxiella spp. , Diplopylidium spp. From the subclass of the Monogenea, for example Gyrodactylus spp. , Dactylogyrus spp. , Polystoma spp. From the subclass of the Digenea, for example Diplostomum spp. , Posthodiplostomum spp. , Schistosoma spp. , Trichobilharzia spp., Ornithobilharzia spp. , Austrobilharzia spp. , Gigantobilharzia spp. , Leucochloridium spp., Brachylaima spp. , Echinostoma spp. , Echinoparyphium spp. , Echinochasmus spp. , Hypoderaeum spp. , Fasciola spp. , Fasciolides spp. , Fasciolopsis spp. , Cyclocoelum spp. , Typhlocoelum spp., Paramphistomum spp. , Calicophoron spp. , Cotylophoron spp. , Gigantocotyle spp. , Fischoederius

spp. , Gastrothylacus spp. , Notocotylus spp. , Catatropis spp. , Plagiorchis spp. , Prosthogonimus spp. , Dicrocoelium spp. , Eurytrema spp. , Troglotrema spp. , Paragonimus spp. , Collyriclum spp., Nanophyetus spp. , Opisthorchis spp. , Clonorchis spp. , Metorchis spp. , Heterophyes spp., Metagonimus spp. From the order of the Enoplida, for example Trichuris spp. , Capillaria spp., . Trichomosoides spp., Trichinella spp. From the order of the Rhabditida, for example Micronema spp. , Strongyloides spp. From the order of the Strongylida, for example Stronylus spp., Triodontophorus spp. , Oesophagodontus spp. , Trichonema spp. , Gyalocephalus spp., Cylindropharynx spp. , Poteriostomum spp. , Cyclococercus spp. , Cylicostephanus spp., Oesophagostomum spp., Chabertia spp. , Stephanurus spp., Ancylostoma spp. , Uncinaria spp., Bunostomum spp. , Globocephalus spp. , Syngamus spp. , Cyathostoma spp. , Metastrongylus spp., Dictyocaulus spp. , Muellerius spp. , Protostrongylus spp. , Neostrongylus spp. , Cystocaulus spp., Pneumostrongylus spp. , Spicocaulus spp. , Elaphostrongylus spp. , Parelaphostrongylus spp., Crenosoma spp. , Paracrenosoma spp., Angiostrongylus spp. , Aelurostrongylus spp. , Filaroides spp. , Parafilaroides spp. , Trichostrongylus spp. , Haemonchus spp. , Ostertagia spp. , Marshallagia spp. , Cooperia spp., Nematodirus spp. , Hyostrongylus spp. , Obeliscoides spp. , Amidostomum spp., Ollulanus spp. From the order of the Oxyurida, for example Oxyuris spp., Enterobius spp. , Passalurus spp. , Syphacia spp. , Aspiculuris spp. , Heterakis spp. From the order of the Ascaridia, for example Ascaris spp. , Toxascaris spp. , Toxocara spp. , Parascaris spp., Anisais spp. , Ascaridia spp. From the order of the Spirurida, for example Gnathostoma spp. , Physaloptera spp. , Thelazia spp. , Gongylonema spp. , Habronema spp. , Parabronema spp. , Draschia spp. , Dracunculus spp.

From the order of the Filariida, for example Stephanofilaria spp. , Parafilaria spp. , Setaria spp. , Loa spp. , Dirofilaria spp. , Litomosoides spp. , Brugia spp., Wuchereria spp. , Onchocerca spp. From the order of the Gigantorhynchida, for example Filicollis spp. , Moniliformis spp. , Macracanthorhynchus spp. , Prosthenorchis spp.

The livestock and breeding stock include mammals, such as, for example, cattle, horses, sheep, pigs, goats, camels, water buffalo, donkeys, rabbits, fallow deer, reindeer, fur-bearing animals, such as, for example, minks, chinchilla or raccoons, birds, such as, for example, chickens, geese, turkeys, ducks or ostriches, freshwater fish and sea fish, such as, for example, trout, carp and eels, reptiles and insects, such as, for example, honey bee and silkworm. The laboratory and test animals include mice, rats, guinea pigs, golden hamsters, dogs and cats. The pets include dogs and cats.

Administration can be effected prophylactically as well as therapeutically.

The active substances are administered, either directly or in the form of suitable preparations, enterally, parenterally, dermally, nasally, by treating the habitat or with the aid of shaped articles

containing the active compound, such as, for example, strips, plates, tapes, collars, ear tags, limb bands or marking devices.

Enteral administration of the active compounds is effected for example orally in the form of powders, tablets, capsules, pastes, drinks, granules, solutions, suspensions and emulsions which can be applied orally, boluses, medicated feed or drinking water. Dermal application is effected, for example, in the form of dipping, spraying, or pouring-on and spotting-on. Parenteral ad- ministration is effected, for example, in the form of injection (intramuscular, subcutaneous, intravenous or intraperitoneal) or by implants.

Suitable preparations include: Solutions, such as solutions for injection, oral solutions, concentrates for oral administration after dilution, solutions for use on the skin or in body cavities, pour-on formulations, gels. Emulsions and suspension for oral or dermal administration and for injection; semi-solid preparations.

Formulations in which the active compound is incorporated in an ointment base or in an oil-in- water or water-in-oil emulsion base. Solid preparations, such as powders, premixes or concentrates, granules, pellets, tablets, boluses, capsules; aerosols and inhalants, shaped articles containing the active compound. Solutions for injection are administered intravenously, intramuscularly and subcutaneously. Solutions for injection are prepared by dissolving the active compound in a suitable solvent and, if desired, adding additives, such as solubilizers, acids, bases, buffer salts, antioxidants, or preservatives. The solutions are sterile-filtered and decanted into con- tainers.

Suitable solvents include: physiologically acceptable solvents, such as water, alcohols, such as ethanol, butanol, benzyl acohol, glycerol, propylene glycol, polyethylene glycols and N-methyl- pyrrolidone, and their mixtures.

If appropriate, the active compounds can also be dissolved in physiologically acceptable vegetable or synthetic oils which are suitable for injection.

Suitable solubilizers include: solvents which facilitate the dissolution of the active compound in the main solvent or which prevent precipitation of the active compound. Examples of solubilizers are polyvinylpyrrolidone, polyethoxylated castor oil and polyethoxylated sorbitan esters.

The following are preservatives: benzyl alcohol, trichlorobutanol, p-hydroxybenzoic esters or n- butanol.

Oral solutions are administered directly. Concentrates are first diluted to the administration concentration and then administered orally. Oral solutions and concentrates are prepared as described above in the case of the solutions for injection, sterile procedures not being necessary- Solutions for use on the skin are applied drop by drop, smoothed on, rubbed in, splashed on or sprayed on. These solutions are prepared as described above in the case of the solutions for injection.

It may be advantageous to add thickeners in the preparation process. The following are thickeners : inorganic thickeners, such as bentonites, colloidal silica, aluminium monostearate, or organic thickeners, such as cellulose derivatives, polyvinyl alcohols and their copolymers, acrylates and methacrylates.

Gels are applied to the skin or smoothed on or introduced into body cavities. Gels are prepared by adding such an amount of thickener to solutions which have been prepared as described for the solutions for injection that a clear composition is formed which has an ointment-like consistency.

The thickeners used are the thickeners indicated further above.

Pour-on and spot-on formulations are poured or splashed onto limited areas of the skin, the active compound penetrating the skin and acting systemically.

Pour-on and spot-on formulations are prepared by dissolving, suspending or emulsifying the active compound in suitable solvents or solvent mixtures which are tolerated by the skin. If appropriate, other auxiliaries, such as colorants, absorption promoters, antioxidants, photostabilizers or tackifiers are added.

Suitable solvents include: water, alkanols, glycols, polyethylene glycols, polypropylene glycols, glycerol, aromatic alcohols, such as benzyl alcohol, phenylethanol or phenoxyethanol, esters, such as ethyl acetate, butyl acetate or benzyl benzoate, ethers, such as alkylene glycol alkyl ethers, such as dipropylene glycol monomethyl ether or diethylene glycol mono-butyl ether, ketones, such as acetone or methyl ethyl ketone, aromatic and/or aliphatic hydrocarbons, vegetable or synthetic oils, DMF, dimethyl-acetamide, N-methylpyrrolidone, or 2, 2-dimethyl-4-oxy-methylene-1, 3-dioxolane.

Colorants are all colorants which can be dissolved or suspended and which are approved for use in animals.

Examples of absorption promoters are DMSO, spreading oils, such as isopropyl myristate, dipropylene glycol pelargonate, silicone oils, fatty acid esters, triglycerides or fatty alcohols.

The following are antioxidants: sulfites or metabisulfites, such as potassium metabisulfite, ascorbic acid, butylhydroxytoluene, butylhydroxyanisole or tocopherol.

An example for photostabilizers is novantisolic acid.

Tackifiers are, for example, cellulose derivatives, starch derivatives, polyacrylates or natural polymers such as alginates or gelatin.

Emulsions can be administered orally, dermally or as injections. Emulsions are either the water-in- oil type or the oil-in-water type. They are prepared by dissolving the active compound either in the hydrophobic or in the hydrophilic phase and by homogenizing this phase with the solvent of the other phase, with the aid of suitable emulsifiers and, if appropriate, other auxiliaries, such as colorants, absorption promoters, preservatives, antioxidants, photostabilizers, and viscosity- increasing substances.

Suitable hydrophobic phases (oils) include: paraffin oils, silicone oils, natural vegetable oils such as sesame seed oil, almond oil or castor oil, synthetic triglycerides, such as caprylic/capric acid biglyceride, a triglyceride mixture with vegetable fatty acids of chain length C812 or other specifically selected natural fatty acids, mixtures of partial glycerides of saturated or unsaturated fatty acids which may also contain hydroxyl groups, and mono-and diglycerides of the C8/Clo- fatty acids, fatty acid esters, such as ethyl stearate, di-n-butyryl adipate, hexyl laurate, dipropylene glycol pelargonate, esters of a branched fatty acid having a medium chain length with saturated fatty alcohols of chain length Cjg-Cig, isopropyl myristate, isopropyl palmitate, caprylic/capric esters of saturated fatty alcohols of chain length Cl2-CI8, isopropyl stearate, oleyl oleate, decyl oleate, ethyl oleate, ethyl lactate, waxy fatty acid esters such as artificial duck uropygial fat, dibutyl phthalate, diisopropyl adipate, ester mixtures related to the latter, etc; fatty alcohols, such as isotridecyl alcohol, 2-octyldodecanol, cetylstearyl alcohol or oleyl alcohol; fatty acids, such as, for example, oleic acid and its mixtures.

Suitable hydrophilic phases include water, alcohols, such as, for example, propylene glycol, glycerol, sorbitol and their mixtures.

Suitable emulsifiers include nonionic surfactants, for example polyethoxylated castor oil, polyethoxylated sorbitan monooleate, sorbitan monostearate, glycerol monostearate, polyoxyethyl stearate or alkylphenol polyglycol ethers; Ampholytic surfactants, such as disodium N-lauryl-ß-iminodipropionate or lecithin;

Anionic surfactants, such as Na lauryl sulfate, fatty alcohol ether sulfates, and the monoethanolamine salt of mono/dialkylpolyglycol ether orthophosphoric ester ; Cation-active surfactants such as cetyltrimethylammonium chloride.

Suitable other auxiliaries include: substances which increase the viscosity and stabilize the emulsion, such as carboxymethylcellulose, methylcellulose and other cellulose and starch deriva- tives, polyacrylates, alginates, gelatin, gum arabic, polyvinylpyrrolidone, polyvinyl alcohol, methylvinyl ether/maleic anhydride copolymers, polyethylene glycols, waxes, colloidal silica, or mixtures of the listed substances.

Suspensions can be administered orally, dermally or as an injection. They are prepared by suspending the active compound in a liquid excipient, if appropriate with the addition of other auxiliaries, such as wetting agents, colorants, absorption promoters, preservatives, antioxidants and photostabilizers. Suitable liquid excipients include all homogeneous solvents and solvent mixtures.

Suitable wetting agents (dispersants) include the surfactants indicated further above. Suitable other auxiliaries include those indicated further above.

Semi-solid preparations can be administered orally or dermally. They are only distinguished from the above-described suspensions and emulsions by their higher viscosity.

To prepare solid preparations, the active compound is mixed with suitable excipients, if appropria- te with the addition of auxiliaries, and the mixture is formulated as desired.

Suitable excipients include all physiologically acceptable solid inert substances. Suitable for this purpose are inorganic and organic substances. Inorganic substances are, for example, common salt, carbonates, such as calcium carbonate, hydrogen carbonates, aluminium oxides, silicas, clays, precipitated or colloidal silica, and phosphates.

Organic substances are, for example, sugars, cellulose, foodstuffs and animal feeds, such as powdered milk, animal meals, cereal meals, coarse cereal meals and starches.

Auxiliaries are preservatives, antioxidants and colorants which have already been mentioned further above.

Other suitable auxiliaries are lubricants and glidants, such as, for example, magnesium stearate, stearic acid, talc, bentonites, disintegrants, such as starch or crosslinked polyvinylpyrrolidone, binders, such as, for example, starch, gelatin or linear polyvinylpyrrolidone, and dry binders, such as microcrystalline cellulose.

In the preparations, the active compounds can also be present in mixtures with synergists or other active compounds which are active against pathogenic endoparasites. Examples of such active compounds are L-2,3, 5,6-tetrahydro-6-phenyl-imidazothiazole, benzimidazole carbamates or pyrantel.

Ready-to-use preparations contain the active compounds in concentrations of 10 ppm to 20 per cent by weight, preferably from 0.1 to 10 per cent by weight.

Preparations which are diluted before use contain the active compounds in concentrations of 0.5 to 90 per cent by weight, preferably from 5 to 50 per cent by weight.

In general it has been found to be advantageous to administer the mixture according to the invention in amounts of from about 10 to about 100 mg of active compound per kg of body weight per day to obtain good results. Preference is given to using from 10 to 50 mg of active compound mixture per kg of body weight.

In the compositions, the weight ratio of praziquantel and/or epsiprantel to depsipeptide is generally 1: 1-10, preferably 1: 1-2 and very particularly preferably 1: 1.

The preparation and application of the compounds of the present invention will be described more specifically by the following examples and test examples. The present invention, however, should not be restricted only to them in any way. "Parts"are"parts by weight", unless specified.

Examples Synthesis Example 1

Acetonitrile (100 ml) was admixed with 5-mercapto-1, 2, 4-thiadiazole (0.35 g), 1-methanesulfonyl- oxy-6,6-difluoro-5-hexene (0.7 g) and potassium carbonate (0.5 g) and the mixture was refluxed for 4 hours. After cooling the reaction solution to room temperature it was filtered by suction and the filtrate was distilled under reduced pressure. The residue was purified by column chromato- graphy (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 %, nD"°=1. 5093).

Synthesis Example 2 After dissolving 5- (6, 6-difluoro-5-hexenylthio-1, 2,4-thiadiazole (0.4 g) in dichloromethane (100 ml), m-chloroperbenzoic acid (0.9 g, purity about 70 %) was added under ice cooling and the mixture was stirred at room temperature for 20 hours. The reaction solution was washed with saturated aqueous solution of sodium hydrogen carbonate (50 ml) twice and the organic layer was dried over magnesium sulfate. After distilling off the solvent 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-hexenylsulfonyl)-1, 2, 4-thiadiazole (0.25g, yield 55%, nD2°=1. 4999).

Synthesis Example 3 After dissolving 5-(6, 6-difluoro-5-hexenylthio)-3-methyl-1, 2,4-thiadiazole (0.5 g) in dichloro- methane (lOOml), m-chloroperbenzoic acid (0. 5 g, purity about 70 %) was added under ice cooling and the mixture was stirred at room temperature for 20 hours. The reaction solution was washed with saturated aqueous solution of sodium hydrogen carbonate (50 ml) twice and the

organic layer was dried over magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by column chromatography (eluent: ethyl acetate: hexane =1: 4) to obtain colorless, oily 5-(6, 6-difluoro-5-hexenylsulfinyl)-3-methyl-1, 2,4-thiadiazole (0.5 g, yield 94%, nD'°=1. 5110).

The compounds of the present invention obtained by similar processes as mentioned above are shown, together with the compounds of Synthesis Examples 1,2 and 3 in the following Table 1.

In the Table Me represents methyl, Et represents ethyl, n-Pr represents n-propyl, iso-Pr represents isopropyl, n-Bu represents n-butyl, sec-Bu represents sec-butyl, t-BU represents tert-butyl, n-Pen represents n-pentyl, cy-Pr represents cyclopropyl, cy-Pen represents cyclopentyl, cy-Hex represents cyclohexyl, and Ph represents phenyl.

Table 1 R l-N N SW) CH2) Comp. NO.., H 2 3 4 5093 5 5159 6 4999 '7'H'0'5 8 9 5137 10 11 4920 12 13 5069 14 15 4879 16 17 18 19 20 5150 21 5110 22 4915 23 24 25 26 27 28. Comp. p 29 30 31 32 33 34 35 36 37 38 39 40 sec-Bu 0 4 41 sec-Bu 1 6 42 5048 43 4835 44 4835 45 46 47 48 49 50 51 52 cy-Pen 0 4 53 54 cy-Hex 0 4 55 56 57 58 59 60 4 61 Gomp. " 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 '78'CFg"I 78 79 CF3 2 4 80 81 82 83 84 5225 85 5141 86 4959 '87EtO7)'4 87 EtO 88 EtO 2 4 iso-PrO 90 91 92 93 94 'Comp . . zo , 95 96 97 98 99 100 101 102 103 104 105 106 107 108 109 110 111 112 5750 113 5770 114 5558 115 116 117 118 119 120 121 122 123 124 125 126 127 n 128 129 130 131 132 133 134 135 136 137'Cl1) 5395 138 5305 139 5098 140 141 142 143 144 145 146 147 148 149 150 151 152 153 154 155 2-pyrimidinyl 0 156 4-pyrimidinyl 157 2-pyradinyl Synthesis Example 4 (Synthesis of starting material)

To ethanol (100 ml), ethylxanthic acid potassium salt (32 g) and formamidine hydrochloride (10.4 g) were added and the mixture was stirred for 30 minutes. To the mixed solution a solution of sulfur 6.4 g in carbon disulfide 100 ml was slowly added dropwise and the mixture was refluxed for 30 hours. After the reaction the solvent was distilled off at less than 40°C under reduced pressure. To the residue, water (150 ml) and 6N aqueous solution of sodium hydroxide (50 ml) were added and the mixture was stirred for 10 minutes. The insoluble matter was filtered off and the filtrate was left standing at room temperature for a day and pH was brought to 3 by adding concentrated hydrochloric acid under ice cooling. The solution was extracted with ethyl acetate (100 ml) 3 times and the organic layer was dried over magnesium sulfate. After distilling off the solvent the residue was purified by column chromatography (eluent: ethyl acetate: hexane = 1: 4) to obtain white crystalline, known 5-mercapto-1, 2,4-thiadiazole (1.25 g, yield 11 %).

Synthesis Example 5 (Synthesis of starting material) 1,5-Pentanediol (55.6 g, 533. 8 mmol) and triethylamine (61 g, 603 mmol) were dissolved in tetrahydrofuran (230 ml), to which p-chlorobenzoyl chloride (46.7 g, 266. 9 mmol) was added dropwise under ice cooling. After finishing the addition and stirring at room temperature for 2 hours, water (150 ml) was added to the reaction solution and the mixture was extracted with toluene. After washing with water, the toluene layer was dried over anhydrous sodium sulfate and the residue was treated by column chromatography (n-hexane: ethyl acetate = 1 : 1) to obtain 1- (p- chlorobenzoyloxy) -5-pentanol (58.89 g). nD2o= 1.5212, yield 91 %.

Synthesis Example 6 (Synthesis of starting material)

Oxalyl chloride (54.82 g, 431.93 mmol) was dissolved in dichloromethane (500 ml), to which a solution of dimethyl sulfoxide (37.5 g, 479.92 mmol) in dichloromethane (100 ml) was added dropwise at-60°C. Then a solution of 1- (p-chlorobenzoyloxy)-5-pentanol (58.24 g, 239.96 mmol) in dichloromethane (80ml) was added thereto dropwise and stirred for 15 minutes. To the solution, triethylamine (121.41 g, 1.2 mol) was added dropwise and stirred for 5 minutes and the reaction was brought to room temperature. To the reaction solution, water (500 ml) was added and the dichloromethane layer was taken up. After drying the dichloromethane layer with anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was treated by column chromatography (n-hexane: ethyl acetate =7: 2) to obtain 1-(p-chlorobenzoyloxy)-5- pentanal (51g). nD20= 1.5220, yield 88%.

Synthesis Example 7 (Synthesis of starting material)

Dibromodifluoromethane (66.52 g, 317 mmol) was dissolved in tetrahydrofuran (300 ml), to which tris- (dimethylamino) phosphine (103.47 g, 634 rnmol) was added dropwise at-78°C. After finishing the addition the reaction solution was stirred for 30 minutes and brought to room temperature. After dropwise addition of a solution of 1- (p-chlorobenzoyloxy)-5-pentanal (38.15 g, 158.5 mmol) in tetrahydrofuran (200 ml) thereto, the solution was stirred for 2 hours. To the reaction mixture, water (600 ml) was added and extracted with ethyl acetate. After washing with water, the ethyl acetate layer was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was treated by column chromatography (n- hexane: ethyl acetate =18: 1) to obtain 1- (p-chlorobenzoyloxy)-6, 6-difluoro- 5-hexene (36.11 g). nDZO= 1.5315, yield 83 %.

Synthesis Example 8 (Synthesis of starting material) HO- (CH2) 4CH=CF2 To a solution of 1- (p-chlorobenzoyloxy)-6, 6-difluoro-5-hexene (36.11 g, 131.45 mmol) in ethanol (80 ml), an aqueous solution (40 ml) of sodium hydroxide (5. 99 g, 149. 86 mmol) was added dropwise and the mixture was stirred at 50°C for 1 hour. After cooling, water (200 ml) was added thereto and the mixture was extracted with ether. After washing with water, the ether layer was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure.

The residue was treated by silica gel chromatography (n-hexane : ethyl acetate =2: 1) to obtain 1- hydroxy-6,6-difluoro-5-hexene (15 g). nid20 1. 3985, yield 84 %.

Synthesis Example 9 (Synthesis of starting material) H3C-S (0) 2-0- (CH2) 4CH=CF2 l-Hydroxy-6, 6-difluoro-5-hexene (22. 14 g, 162.62 mmol) and triethylamine (18 g, 178.89 mmol) was dissolved in dichloromethane (400 ml) and methanesulfonyl chloride (20.48 g, 178.89 mmol) was added dropwise to the solution under ice cooling. After stirring the mixture at room tempe- rature for 30 minutes, water (300ml) was added thereto and the organic layer was taken up. After washing with water, the organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was treated by column chromatography (n- hexane: ethyl acetate =3 : 1) to obtain 1-methanesulfonyloxy-6, 6-difluoro-5-hexene (27.43g). nD2o= 1. 4210, yield 79 %.

Test Example 1: Test against Meloidogyne spp. (Soil pot test) Preparation of test agent 1 Part of the active compound is impregnated to 99 parts of pumice to make fine granules.

Test method The test agent prepared as mentioned above was added to the soil contaminated by Meloidogyne incognita so that the chemical concentration would be lOppm. The soil and the test agent were homogeneously mixed by stirring and a pot (1/5000 are) was filled with the soil. About 20 seeds of tomato (variety: Kurihara) were sown per pot. After cultivation in a greenhouse for 4 weeks, they were carefully pulled out not to damage the roots and the root knot index and the controlling effect were determined as follows.

Degree of damage : 0: No knots were formed (Complete control) 1: A few knots were formed.

2: Knots were formed to a medium extent.

3: Knots were formed to an intense extent.

4: Knots were formed to the most intense extent (which corresponds to non-treatment).

E (degree of damage x number of individuals) Root knot index x 100 Total number of tested individuals x 4 The controlling effect of the compounds tested can then be evaluated according to the following equation: (Root knot index at (Root knot index at non-treated area) -treated area) Controlling effect [%] = x 100 Root knot index at non-treated area For example, in the test described, the following compounds showed a controlling effect of 100% at an effective concentration of 10 ppm: No. 4 and 5.

Test Example 2: Herbicidal activity (pre-emergence soil treatment against field weeds) Preparation of formulation of the active compound Carrier : Acetone 5 parts by weight Emulsifier : Benzyloxy polyglycol ether 1 part by weight A formulation of an active substance is obtained as an emulsifiable concentrate by mixing 1 part by weight of the active compound with the above-mentioned amount of the carrier and emulsifier.

A prescribed amount of the formulation is diluted with water.

Test method In the greenhouse, on the surface layer of a (120 cm2 pot filled with field soil, seeds of Echiizochloa crusgalli, Setaria viridis, Amaranthus retroflexus and Polygonum were sown and covered with soil. A diluted solution of the prescribed amount of each active compound prepared according to the aforementioned method was spread uniformly on the surface layer of each pot.

The herbicidal effect was examined 2 weeks after the treatment.

Results As a result, for example, the compounds No. 5 and 6 showed herbicidal activity of more than 90% against Ec/ocoa crusgalli, Setaria viridis, Amaranthus retroflexus and Polygonum at an application rate of the active compound of 2 kg/ha..

Test Example 3: Herbicidal activity (post-emergence foliage treatment against field weeds) Test method In a greenhouse, seeds of Echinochloa crusgalli, Setaria viridis, Amaranthus retroflexus and Polygonum were sown on the surface layer of a 120 cm2 pot filled with field soil and covered with soil. Ten days after the sowing (2-leaf stage in average) a diluted solution of the prescribed amount of each active compound prepared in the same manner as in the above-mentioned Test Example 2 was spread uniformly on the foliage of the plants in each pot. The herbicidal effect was examined 3 weeks after the treatment.

Results As a result, for example, the compounds No. 6 and 86 showed herbicidal activity of more than 90% against Echinochloa crusgalli, Setaria viridis, Amaranthus retroflexus and Polygonum at an application rate of the active compound of 2 kg/ha.

Formulation Example 1 (Granule) To a mixture of 10 parts of the compound of the present invention (No. 4), 30 parts of bentonite (montmorillonite), 58 parts of talc and 2 parts of ligninsulfonate salt, 25 parts of water were added, well kneaded, made into granules of 10-40 mesh by an extrusion granulator and dried at 40-50°C to obtain granules.

Formulation Example 2 (Granule) 95 Parts of clay mineral particles having a particle diameter distribution in the range of 0.2-2 mm are put in a rotary mixer. While rotating it, 5 parts of the compound of the present invention (No.

4) are sprayed together with a liquid diluent, wetted uniformly and dried at 40-50°C to obtain granules.

Formulation Example 3 (Emulsifiable concentrate) 30 Parts of the compound of the present invention (No. 4), 55 parts of xylene, 8 parts of polyoxyethylene alkyl phenyl ether and 7 parts of calcium alkylbenzenesulfonate are mixed and stirred to obtain an emulsifiable concentrate.

Formulation Example 4 (Wettable powder) 15 Parts of the compound of the present invention (No. 5), 80 parts of a mixture of white carbon (hydrous amorphous silicon oxide fine powders) and powder clay (1: 5), 2 parts of sodium alkylbenzenesulfonate and 3 parts of sodium alkylnaphthalenesulfonate-formalin-condensate are crushed and mixed to make a wettable powder.