MXPA99010488A

MXPA99010488A - Use of pesticide and parasiticide of compounds of 1-aril-1- (tio, sulfinyl, and sulfonyl-substitute) -2-nitroet

Info

Publication number: MXPA99010488A
Application number: MXPA/A/1999/010488A
Authority: MX
Inventors: Wakefield Wood William; Enos Annmarie
Original assignee: Basf Aktiengesellschaft
Priority date: 1998-11-16
Filing date: 1999-11-15
Publication date: 2000-10-01

Abstract

The present invention relates to the pesticidal use of 1-aryl-l- (thio, sulfinyl and sulfonyl-substituted) -2-nitroethane compounds having the structural formula

Description

USE OF PESTICIDE AND PARASITICIDE OF COMPOUNDS OF 1-ARILLO- (TIO, SULFINYL, AND SULFONYL-REPLACED) -2- NITROETHANE BACKGROUND OF THE INVENTION Pests of nematodes, insects and acarids destroy crops and crops. In the United States, agronomic crops must compete with thousands of such pests. In addition, helminth parasites cause hundreds of millions of dollars of economic damage on a global basis annually in the poultry and domestic animal sectors. In spite of the commercial pesticides and parasiticides that can be obtained at the moment, damages are still observed in the crops, poultry and domestic animals. Therefore, investigations are carried out continuously to create new and more effective pesticides and parasiticides. Some ß-nitrophenethyl derivatives that are useful as fungicidal agents have been described in the Japanese Patent 62039563. However, this application does not disclose or suggest any nematicidal, insecticidal and acaricidal utility for the ß-nitrophenethyl derivatives described herein. REF .: 31864 Therefore, it is an object of the present invention to provide a method for the control of parasites and pests of helminths, nematodes, insects and acarids. It is also an object of the present invention to provide a method for the protection of the crop and crops against the infestation and attack of nematodes, insects and acarids. It is another object of this invention to provide a method to treat, control, prevent and protect warm-blooded animals, fish and humans against infestation and infection caused by helminths. These and other objects of the present invention will become more apparent in the description thereof indicated below.

SUMMARY OF THE INVENTION The present invention provides a method for the control of parasites or pests of helminths, nematodes, insects or acarids that comprises contacting said pests or parasites or their provision of food, habitat or breeding places with a pesticidally or parasiticidally effective of a 1-aryl-1- (thio, sulfinyl or sulfonyl-substituted) -2-nitroethane compound having the structural formula I ? o2 (i). wherein Ar 'is phenyl optionally substituted with any combination of 1 to 5 halogen atoms, one or two cyano groups, one or two nitro groups, one to three C? -C alkyl groups, one to three haloalkyl C groups? C one to three C? -C alkoxy groups, one to three C? -C4 haloalkoxy groups, one to three C? -C alkylthio groups, one to three haloalkylthio C? C groups, a benzylthio group or a group SCH2C02R2, 2-naphthyl optionally substituted with any combination of 1 to 5 halogen atoms, one or two cyano groups, one or two nitro groups, one to three C alquilo ~C alkyl groups, one to three C halo-C haloalkyl groups , one to three C 1 -C 4 alkoxy groups, one to three C 1 -C 4 haloalkoxy groups, one to three C 1 -C alkylthio groups, one to three C 1 -C 4 haloalkyl groups, piperonyl optionally substituted with any combination of to 3 halogen atoms, one or two cyano groups, one or two nitro groups, one to three C alquilo-C4 alkyl groups, one to three C-C haloalkyl groups, one to three groups s C 1 -C alkoxy, one to three C 1 -C 4 haloalkoxy groups, one to three C 1 -C alkylthio groups, one to three optionally substituted C 1 -C 4, 2, 3 or 4-pyridyl halo-alkylthio groups with any combination of 1 to 4 halogen atoms, one or two cyano groups, one or two nitro groups, one to three C1-C4 alkyl groups, one to three C4 haloalkyl groups ,. one to three C1-C4 alkoxy groups, one to three C1-C4 haloalkoxy groups, one to three C1-C4 alkylthio groups, one to three C1-C4 halo-alkylthio, 2- or 3-furyl groups optionally substituted with any combination of 1 to 3 halogen atoms, one or two cyano groups, one or two nitro groups, one to three alkyl groups, one to three C1-C4 haloalkyl groups, one to three C1-C4 alkoxy groups, one to three C1-C4 haloalkoxy groups , one to three alkylthio C? -C4 groups, one to three haloalkyl groups C1-C4, 2- or 3-thienyl optionally substituted with any combination of 1 to 3 halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups, one to three C 1 -C 4 haloalkoxy groups, one to three C 1 -C 4 alkylthio groups, one to three halo groups; C1-C4 alkylthio, R is hydrogen, C02R3, C (0) NR4R5, (CH2) nCR2 (NR4R CO_R, CH (0RS) CH20R7, CH (CH20R8) SCH (R9) CH2N02, alkyl C.-C, haloalkyl C ? -C, C2-C alkenyl, C2-C-haloalkenyl, phenyl optionally substituted with any combination of one to five halogen atoms, one or two cyano groups, one or two nitro groups, one to three C? ~ C alkyl groups , one to three haloalkyl C: -C4 groups, one to three C1-C4 alkoxy groups, one to three haloalkoxy groups C1-C4, one to three C1-C4 alkylthio groups, or one to three C1-C4, 2-, or 3-furyl Kaloalkylthio groups optionally substituted with any combination of 1 to 3 halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups, one to three C 1 -C 4 haloalkoxy groups, one to three C 1 -C 4 alkylthio groups, one to three haloalkyl groups C 1 -C 4, 2 or 3-thienyl optionally substituted with any combination of 1 to 3 halogen atoms, one or two cyano groups, one or two nitro groups, one to three C1-alkyl groups C4, one to three C1-C4 haloalkyl groups, one to three C1-C4 alkoxy groups, one to three C1-C4 haloalkoxy groups, one to three C4-4 alkylthio groups, one to three C1-C4 haloalkyl groups, 'R2 , R6, R and Re are each independently hydrogen or C? -C3 alkyl; m is 0, 1 or 2, • n is 0 or 1; R9 is phenyl optionally substituted with any combination of 1 to 5 halogen atoms, one or two cyano groups, one or two nitro groups, one to three C? -C4 alkyl groups, one to three C1-C4 haloalkyl groups, one to three C1-C4 alkoxy groups, one to three C?-C4 haloalkoxy groups, one to three C1-C4 alkylthio groups, one to three haloalkylthio C? ~C groups, R 3 is hydrogen, C 1 -C 10 alkyl, CH 2 (Ci-Cu haloalkyl) , C3-C10 alkenyl, C3-C10 haloalkenyl, a benzyl cation optionally substituted on the ring with any combination of 1 to 5 halogen atoms, one or two cyano groups, one or two nitro groups, one to three C1-C4 alkyl groups , one to three C1-C4 haloalkyl groups, one to three C1-C4 alkoxy groups, one to three C1-C4 haloalkoxy groups, one to three C1-C4 alkylthio groups, one to three C1-C4 haloalkylthio groups, or optionally substituted phenyl with any combination of 1 to 5 halogen atoms, one or two giano groups, one or two nitro groups, one to three C1 alkyl groups -C4, one to three C1-C4 haloalkyl groups, one to three C1-C4 alkoxy groups, one to three C4-4 haloalkoxy groups, one to three C4-4 alkylthio groups, one to three C1-C4 haloalkyl groups, R4 and R5 are each independently hydrogen, C1-C10 alkyl, CH2 (C1-C10 haloalkyl), C-C alkenyl, C3-C10 haloalkenyl, benzyl optionally substituted on the ring with any combination of one to five halogen atoms , one or two cyano groups, one or two nitro groups, one to three C1-C4 alkyl groups, one to three C1-C4 haloalkyl groups, one to three C?-C4 alkoxy groups, one to three C1-C4 haloalkoxy groups, one to three C 1 -C 4 alkylthio groups, one to three C 1 -C 4 haloalkylthio groups, or phenyl optionally substituted with any combination of 1 to 5 halogen atoms, one or two cyano groups, one or two nitro groups, one to three groups C 1 -C 4 alkyl, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups, one to three C 1 -C 4 haloalkoxy groups, one to three C 1 -C 4 alkylthio groups , one to three C1-C4 haloalkylthio groups, and when R4 and R5 are taken together with the atom to which they are attached, they can form a one or six member ring where R4R5 is represented by: - (CH_) 4 -, - ( CH2) 5-0- (CH2) 20 (CH2) 2-; and Ri is hydrogen, C1-C4 alkyl, or phenyl optionally substituted with any combination of 1 to 5 halogen atoms, one or two cyano groups, one or two nitro groups, one α-three alkyl groups * d-C4, one a three C1-C4 haloalkyl groups, one to three C1-C4 alkoxy groups, one to three C1-C4 haloalkoxy groups, one to three C1-C4 alkylthio groups, one to three C1-C4 haloalkyl groups, This invention also comprises pesticidal compositions and parasiticides containing said compounds. Advantageously it has been found that the compounds 1-aryl-1 - (thio, sulfinyl and sulfonyl-substituted) -2-nitroethane and the compositions containing them are especially useful for the control of nematode pests.

DETAILED DESCRIPTION OF THE INVENTION The present invention provides a method for the control of parasites or pests of helminths, nematodes, insects or acarids that comprises contacting said pests or parasites, the place where they are fed, their habitat or breeding places with a pesticidally or parasitically effective amount of a 1-aryl-1- (thio, sulfinyl or sulfonyl-substituted) -2-nitroethane compound of formula I.

Preferred pesticidal agents of formula I include: { [alpha- (Nitromethyl) benzyl] thio} methyl acetate; acid { [alpha- (Nitromethyl) benzyl] thio} acetic acid; . { [p-methyl-alpha- (nitromethyl) benzyl] thio} ethyl acetate; . { [alpha- (Nitromethyl) benzyl] thio} acetate of butilo; . { 3,4- (methylenedioxy) -alpha- (nitromethyl) benzyl] thio} methyl acetate; . { 3,4- (methylenedioxy) -alpha- (nitromethyl) benzyl] thio} ethyl acetate; . { 3,4- (methylenedioxy) -alpha- (nitromethyl) benzyl] thio} acetate of butilo; . { [p-methyl-alpha- (nitromethyl) benzyl] thio} methyl acetate; . { [p-methyl-alpha- (or trometyl) benzyl] thio} acetate of butilo; . { [o-fluoro-alpha- (nitromethyl) benzyl] thio} methyl acetate; . { [o-fluoro-alpha- (nitromethyl) benzyl] thio} ethyl acetate; . { [o-flúqr-alpha- (nitromethyl) benzyl] thio} acetate of butilo; . { [p-methoxy-alpha- (nitromethyl) benzyl] thio} methyl acetate; . { [p-methoxy-alpha- (nitromethyl) benzyl] thio} ethyl acetate; . { [p-methoxy-alpha- (nitromethyl) benzyl] thio} acetate of butilo; p- [1- (allylthio) -2-nitroethyl] anisole; . { [m-methoxy-alpha- (nitromethyl) benzyl] thio} methyl acetate; . { [m-methoxy-alpha- (nitromethyl) benzyl] thio} ethyl acetate; acid { [p-fluoro-alpha- (nitromethyl) benzyl] thio} acetic; acid { [3,4- (methylenedioxy) -alpha- (nitromethyl) benzyl + thio-} "-acetic acid; {. [2-nitro-l- (p-tolyl) ethyl] thio.} acetic acid; {. [p-isopropyl-alpha- (nitromethyl) benzyl] thio.} acetic acid. acid { [o-Fluoro-alpha- (nitromethyl) benzyl] thio.} acetic acid { [m-methoxy-alpha- (nitromethyl) benzyl] thio.} acetic acid. p-methoxy-alpha- (nitromethyl) benzyl] thio., acetic acid, {. [p-chloro-alpha- (nitromethyl) benzyl] thio.} acetic acid, 2,3-bis { (nitromethyl) benzyl] thio.) -1-propanol; 3- {[[alpha- (nitromethyl) benzyl] thio} alanine; acid { [2-nitro-l- (2-thienyl) ethyl. ] acetic acid; {. [2-nitro-l- (2-thienyl) ethyl] thio.} ethyl acetate; 2- [1- (allylthio) -2-nitroethyl] thiophene; [1-allylthio) -2-nitroethyl] pyridine, among others The most preferred pesticidal agents of this invention which are especially useful for the control of nematodes include: { [Alpha- (nitromethyl) benzyl] thio.} Acetate. of methyl; acid { [alpha- (nitromethyl) b acetic acid. . { [p-methyl-alpha- (nitromethyl) benzyl] thio} ethyl acetate; . { [3,4- (methylenedioxy) -alpha- (nitromethyl) benzyl] -thio} ethyl acetate; . { [p-methyl-alpha- (nitromethyl) benzyl] thio} methyl acetate; acid { [p-methoxyl-alpha- (nitromethyl) benzyl] thio} ethyl acetate and "" acid. { [p-fluoro-alpha- (nitromethyl) benzyl] thio} acetic; acid { [3, 4- (methylenedioxy) -alpha- (nitromethyl) benzyl] -thio} acetic acid { [2-nitro-1- (p-tolyl) ethyl} acetic; acid { [p-isopropyl-alpha- (nitromethyl) benzyl] thio} acetic; acid { [o-fluoro-alpha- (nitromethyl) benzyl] thio} acetic; acid { [m-methoxy-alpha- (nitromethyl) benzyl] thio} acetic; acid { [p-methoxy-alpha- (nitromethyl) benzyl] thio} acetic; 2, 3-bis. { [alpha- (Nitromethyl) encyl] thio} -1-propanol; Y 3- . { [alpha- (Nitromethyl) encyl] thio} to the girl; among others. The present invention also provides a method for the protection of crop plants against attack or infestation caused by nematodes, insects or acarids, which comprises applying to the foliage of plants, or to the soil, or to water where they grow a quantity pesticidally. of a 1-aryl-l (thio, sulfinyl or substituted sulfonyl) -2-nitroethane compound of the formula 1. The compounds of formula I of this invention are useful for the control of parasitic nematodes and nematodes that develop freely on the ground. The parasitic nematodes of plants include but are not limited to ectoparasites such as Xiphimema spp., Longidorus spp. and Trichodorus spp., semi-parasites such as Tylenchulus spp., migratory endoparasites such as Pratylenchus spp., Radopholus spp., and Scutellonema spp., sedentary parasites such as Heterodera spp., Globodera spp., and Meloidogyne spp., and endoparasites. of the stem and leaves such as Ditylenchus spp., Aphelenchoides spp. and Hirrshmaniella spp. The 1-aryl-1- (thio, sulfinyl, substituted sulfonyl) -2-nitroethane compounds of formula I are also useful for controlling pests and insects and / or acarids Insects controlled by the compounds of the formula I of this invention include but are not limited to lepidoptera such as tobacco budworms, cabbage caterpillars, cotton weevils, beet scythe, southern scythes and moths; Homoptera such as aphids, leafhoppers, grasshoppers and whiteflies; tisaptera such as thrips, coleoptera such as cotton weevils, Colorado potato weevils, southern corn rootworms, western corn rootworms and mustard weevils and orthoptera such as cicadas, crickets, grasshoppers and cockroaches. Acarides controlled by the compounds of formula I of this invention include but are not. limited to mites such as spider mites, carmine spider mites, grass mites, strawberry mites, citrus mites and leprosis mites. In practice, generally approximately 0. 1 ppm to about 10,000 ppm and preferably about 1 ppm to about 5000 ppm of a compound of formula 1, dispersed in water or in another liquid carrier, is effective when applied to the plants or soil or water in which they grow the plants or where they will be cultivated to protect said plants against the infestations and attacks of nematodes, insects and / or acarids. The 1-aryl-1- (thio, sulfinyl and sulfonyl-substituted) -2-nitroethane compounds are also effective for controlling pests of nematodes, insects and / or acarids when applied to the foliage of plants and / or soil or to the water in which said plants grow or where they will be grown, in an amount sufficient to provide a regime of approximately 0.1 kg / hectare to 0.4 kg / hectare of active ingredient. Although the compounds of formula I of this invention are effective for controlling pests of nematodes, insects and / or acarids or agronomic crops, both in crops and in crops when used alone they can be used only in combination with other biological agents used in agriculture including but not limited to other nematicides, insecticides and / or acaricides. For example, the compounds of the formula I of this invention can be used effectively together in combination with pyrethroids, phosphates, carbamates, cyclodienes, Bacillus thuriggiensis (Bt) endotoxins, fomamidines, phenol tin compounds, chlorinated hydrocarbons, benzoylphenyl ureas, pirróles and similars. The compounds of this invention can be formulated as emulsifiable concentrates, flowable concentrates or wettable powders which are diluted with water or other suitable polar solvent generally in situ, and then applied as a diluted spray. Said compounds may also be formulated in the form of dry compacted granules, granulated formulations, powders, powder concentrates, concentrate suspensions, microemulsions and the like, all of which may be applied to seeds, soil, water and / or foliage to grant to the plant the protection required. Said formulations and compositions of the present invention include a compound of formula I of this invention (or combinations thereof in admixture with one or more agronomically acceptable inert solid or liquid carriers.) Such compositions contain a pesticidally effective amount of said compound or compounds. The amount of which may vary depending on the particular compound, the target pest and the method of use, The person skilled in the art will be able to easily determine which is the pesticidally effective amount without undue experimentation. control, avoid and protect warm-blooded animals including humans and fish against helminth infestation and infection comprising administering orally, topically or parenterally or applying to said animals an anthelminthically effective amount of a 1-aryl-1 compound - (thio, sulfinyl or sulfonyl-substituted) -2-nitroethane of formula 1. The above method is particularly useful for controlling and preventing parasitic helminth infections in animals such as cattle, sheep, swine, camels, deer, horses, poultry, fish, rabbits, goats, dogs and cats, as well as in humans.

Helminthiasis is a widespread disease that is found in many farm and domestic animals and is responsible for significant economic losses throughout the world. Among the helminths that cause significant damage are members of the class of trematodes commonly known as flattened worms, especially members of the genera Fasciola, Fascioloides, Paramphistomun, Dicrocoelium, Eurytrema, Ophisthorchis, Fasciolopsis, Echinostoma, Paragonimus and the like. Helminthia is also caused by a group of worms called nematodes. Nematodes cause serious damage to the walls and tissues of the organs in which it resides, including the intestinal tract, the heart, lungs and blood vessels and are the main cause of anemia. If left untreated they can result in the death of infected animals. The nematodes commonly found in the infecting agents of warm-blooded animals include the genera Haemonchus, Ostertagia, Cooperia, Oesphagastomum, Acyclostoma, Ascaris and the like. Advantageously, the compounds of the formula I of this invention are useful against helminthic agents.

For oral administration to warm-blooded animals, the compounds of formula I can be formulated as animal feeds, animal feed premixes, animal feed concentrates, lozenges, pastes, suspensions, solutions, gels, tablets, boluses and capsules In addition, the compounds of the formula I can be administered to the animals together with the water they drink. For oral administration, the dosage form chosen should provide the animal with about 0.01 mg / kg to 100 mg / kg body weight of the animal per day of the compound of formula I. Alternatively, the compounds of formula I may administered to animals parenterally, for example by intra-ruminal, intramuscular, intravenous or subcutaneous injection or by transdermal methods. The compounds of the formula I can be dispersed or dissolved in a physiologically injectable carrier for injection or by transdermal application. Alternatively, the compounds of the formula I can be formulated in an implant for subcutaneous administration. For parenteral administration the dosage chosen should provide the animal with approximately 0.01 mg / kg, at 100 mg / kg body weight of the animal per day of a compound of the formula, 1. The compounds of the formula I can also be applied topically to animals in the form of baths, powders, collars, medallions, sprays and fluid formulations. For topical application, baths and sprays usually contain about 0.5 ppm to 5000 ppm, preferably about 1 ppm to 3000 ppm, to the compound of formula I. In addition, the compounds of formula I can be formulated as ear tags, particularly for quadrupeds such as cattle and sheep. The compounds of the formula I of the invention can also be used in combination or with one or more parasiticidal compounds, including but not limited to anthelmintics such as benzimidazoles, piperazine, levamisole, pyrantel, praziquantel and the like; endectocides such as avermectins, milbemycins and the like; ectoparasiticides such as arylpyrroles, organophosphates, carbamates, gomabutyric acid inhibitors including fipronil, pyrethroids, spinosads, imidacloprid and the like; regulators of insect development such as pyriproxyfen, cyromazine and the like; and chitin synthase inhibitors such as benzoyl ureas including flufenoxuron. Compounds of formula I can be used in combination or in combination with one or more conventional synergists such as piperonyl butoxide, N-octyl bicycloheptene dicarboximide, dipropyl pyridine-2, 5- dicarboxylate and 1,5a, 6, 9, 9a, 9b-hexahydro-4a (4H) -dibenzofurancarboxaldehyde to improve efficiency, expand the spectrum and provide a convenient method for the control of parasites. The parasiticidal compositions of the present invention include a compound of the formula I of this invention (or combinations thereof) in admixture with one or more inert solid or liquid pharmaceutical and / or agronomically acceptable carriers. Said compositions contain a parasiticidally effective amount of said compound or compounds. Those skilled in the art will be able to easily determine which is the parasiticly effective amount without undue experimentation. The present invention also provides new 1-aryl-1- (thio, sulfinyl or sulfonyl-substituted) -2-nitroethane compounds having the structural formula NO,. { the} wherein Ar is phenyl optionally substituted with any combination of 1 to 5 halogen atoms, one or two cyano groups, one or two nitro groups, one to three C1-C4 alkyl groups, one to three C1-C4 haloalkyl groups, one to three C1-C4 alkoxy groups, one to three C1-C haloalkoxy groups, one to three C1-C4 alkylthio groups, one to three C1-C4 halo-alkylthio groups, a benzylthio group or a SCH2C02R2 group, the 2-naphthyl optionally substituted with any combination of 1 to 5 halogen atoms, one or two cyano groups, one or two nitro groups, one to three C1-C4 alkyl groups, one to three C1-C4 haloalkyl groups, one to three C1-C4 alkoxy groups, one to three C1-C4 haloalkoxy groups, one to three C1-C4 alkylthio groups, one to three C1-C4 halo-alkylthio groups, piperonyl optionally substituted with any combination of 1 to 3 halogen atoms, one or two cyano groups, one or two nitro groups, one to three alkyl groups C1-C4, one to three haloalkyl groups C: -C4, one to three C1-C4 alkoxy groups, one to three haloalkoxy C? ~ C groups, one to three C1-C4 alkylthio groups, one to three halo-alkylthio C1 groups -C4, 2-, 3- or 4-pyridyl optionally substituted with any combination of 1 to 4 halogen atoms, one or two cyano groups, one or two nitro groups, one to three C1-C4 alkyl groups, one to three groups C4-C4 haloalkyl, one to three C1-C4 alkoxy groups, one to three C4-C4 haloalkoxy groups, one to three C4-C4 alkylthio groups, one to three C1-C4 halo-alkylthio groups, 2- or 3- furilo or optionally substituted with any combination of 1 to 3 halogen atoms, one or two cyano groups, one or two nitro groups, one to three C1-C4 alkyl groups, one to three C1-C4 haloalkyl groups, one to three C alkoxy groups? -C4, one to three C1-C4 haloalkoxy groups, one to three C1-C4 alkylthio groups, one to three C1-C4 halo-alkylthio, 2- or 3-thienyl groups optionally substituted with any combination of 1 to 3 halogen atoms , one or two cyano groups, one or two nitro groups, one to three C1-C4 alkyl groups, one to three C1-C4 haloalkyl groups, one to three C1-C4 alkoxy groups, one to three C1-C4 haloalkoxy groups, one to three C 1 -C 4 alkylthio groups, one to three C 1 -C 4 halo-alkylthio groups, R is hydrogen, C 0 2 R 3, C (0) NR 4 R 5, (CH i) n CR 2 (NR 4 R CO.R, CH (OR 6) CH 20 R 7, CH ( CH20R8) SCH (R9) CH2N02, C ^ -C alkyl. , C 1 -C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, phenyl optionally substituted with any combination of one to five halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 - alkyl groups C4, one to three C1-C4 haloalkyl groups, one to three C1-C4 alkoxy groups, one to three C1-C4 haloalkoxy groups, one to three C1-C4 alkylthio groups, or one to three C1-C4 haloalkyl groups, 2- or 3-furyl optionally substituted with any combination of 1 to 3 halogen atoms, one or two cyano groups, one or two nitro groups, one to three C1-C4 alkyl groups, one to three C1-C4 haloalkyl groups, one to three C1-C4 alkoxy groups, one to three C1-C4 haloalkoxy groups, one to three C1-C4 alkylthio groups, one to three C1-C4 halo-alkylthio groups, 2- or 3-thienyl optionally substituted with any combination of 1 to 3 halogen atoms, one or two cyano groups, one or two nitro groups, one to three C1-C4 alkyl groups, one to three C1-C4 haloalkyl groups, one to three C1-C4 alkoxy groups, one to three C1-C4 haloalkoxy groups, one to three C1-C4 alkylthio groups, one to three C1-C4 haloalkylthio groups, R2, R5, R? and Re are each independently hydrogen or Ci-Cß alkyl, * m is "0 ~," "1 or 2; n is 0 or 1; Rg 'is phenyl optionally substituted with any combination of 1 to 5 halogen atoms, one or two cyano groups, one or two nitro groups, one to three C? -C4 alkyl groups, one to three C1-C4 haloalkyl groups, one a three C1-C4 alkoxy groups, one to three C1-C4 haloalkoxy groups, one to three C1-C4 alkylthio groups, one to three C1-C4 haloalkyl groups, RJ is hydrogen, C1-C10 alkyl, CH2 (Ci-Cd haloalkyl. ), C3-C10 alkenyl, C3-C10 haloalkenyl, a benzyl cation optionally substituted on the ring with any combination of 1 to 5 halogen atoms, one or two cyano groups, one or two nitro groups, one to three C1- alkyl groups C4, one to three C1-C4 haloalkyl groups, one to three C?-C4 alkoxy groups, one to three C1-C4 haloalkoxy groups, one to three C1-C4 alkylthio groups, one to three C1-C4 haloalkyl groups, or phenyl optionally substituted with any combination of 1 to 5 halogen atoms, one or two cyano groups, one or two nitro groups, one to three alkyl groups, C? -C4, one to three C1-C4 haloalkyl groups, one to three C1-C4 alkoxy groups, one to three C? -C4 haloalkoxy groups, one to three C? -C4 alkylthio groups, one to three haloalkylthio C groups ? -C, R4 and R5 are each independently hydrogen, Ci-Cuo alkyl, CH2 (Ci-Cio haloalkyl), C3-C1 alkenyl, C3-C10 haloalkenyl, benzyl optionally substituted on the ring with any combination of one to five atoms of halogen, one or two cyano groups, one or two nitro groups, one to three C1-C4 alkyl groups, one to three C1-C4 haloalkyl groups, one to three C1-C4 alkoxy groups, one to three C1-C4 haloalkoxy groups , one to three C 1 -C 4 alkylthio groups, one to three C 1 -C 4 haloalkylthio groups, or phenyl optionally substituted with any combination of 1 to 5 halogen atoms, one or two cyano groups, one or two nitro groups, one to three groups C1-C4 alkyl, one to three C1-C4 haloalkyl groups, one to three C1-C4 alkoxy groups, one to three C1-C4 haloalkoxy groups, one to three alkylityl groups or C1-C4, one to three C1-C4 haloalkylthio groups, and when R4 and R5 are taken together with the atom to which they are attached, they can form a one or six member ring where R4R5 is represented by: - (CH) 4 -, - (CH2) 5-o- (CH2) 20 (CH2) 2-; and Ri is hydrogen, C 1 -C 4 alkyl, or phenyl optionally substituted with any combination of 1 to 5 halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three groups C1-C4 haloalkyl, one to three C1-C4 alkoxy groups, one to three C1-C4 haloalkoxy groups, one to three C1-C4 alkylthio groups, one to three C1-C4 haloalkylthio groups, and with the proviso that Ar is different of phenyl optionally substituted with any combination of one to three halogen atoms, one or two nitro groups, one or two cyano groups, one or three C1-C4 alkyl groups, one to three C1-C4 haloalkyl groups, one to three alkoxy groups C1-C4, or one to three C1-C4 haloalkoxy groups when R is: (1) C02R3 and R3 is hydrogen or C1-C10 alkyl, (2) C1-C4 alkyl, or (3) phenyl optionally substituted with one to five halogen atoms. Examples of halogen mentioned above are fluorine, bromine and iodine. The terms "haloalkyl C_- C4", "haloalkyl C? -C10", "haloalkoxy dC", "haloalkylthio C1-C4", "haloalkenyl C -C,", "haloalkenyl C3-C10", are defined as a group C1-C4 alkyl, a C1-C10 alkyl group, a C1-C4 alkoxy group, a C1-C4 alkylthio group, a C2-C4 alkenyl group and a C3-C10 alkenyl group substituted with one or more halogen atoms respectively. As used in formulas I and above, the cation designates alkali metals, alkaline earth metals, manganese, copper, iron, zinc, cobalt, lead, silver, nickel, ammonium or organic ammonium. The alkali metals include sodium, potassium and lithium. The alkaline earth metals include calcium and magnesium. Organic ammonium cations include but are not limited to monoalkylammonium, dialkylammonium, trialkylammonium, tetraalkylammonium, monoalkenyl, dialkenylammonium, trialkenylammonium, monoalkylammonium, dialkylammonium, monoalkanolammonium, dialkanolammonium, C5-C6 cycloalkylammonium, piperidinium, morpholinium, pyrrolidinium, benzylammonium and the like.

The compounds of formula I of this invention in which m is 0 can be prepared by the reaction of an l-aryl-2-nitroethylene compound having structural formula II with a substituted thiol compound having structural formula III and a base in the presence of a solvent as shown below in the flow diagram I FLOW DIAGRAM I DO NOT.

The compounds of formula I in which m is 1 or 2 can be prepared as shown in flow diagram II, by oxidation of a compound of formula I wherein m is 0 with conventional oxidizing agents such as 3-chloroperoxybenzoic acid and the like in the presence of a solvent.

FLOW DIAGRAM I I DO NOT. l? DO NOT. 0 (m = 1 2) In addition, some compounds of formula I can be converted to other compounds of formula I by the use of conventional procedures that are known to those skilled in the art. The starting compounds of l-aryl-2-nitroethylene of formula II are known in the art and can be prepared by the methods described by R. Jacobo et al in Journal of Flúorine Chemistry, 67 pp. 253-255 (1994) and A. Jara et al in Synthetic Communications, 2483), pp. 417-426 (1994). The substituted thiol compounds of formula III are also known in the art and can be prepared according to the procedures described by Baker et al in Journal of Organic Chemistry, 12, pp. 138-154 (1947). To facilitate a better understanding of the invention, the following examples are presented to illustrate more specific details thereof. The invention is not limited thereto except as defined in the claims.

EXAMPLES 1-205 Preparation of acid. { (alpha- (nitromethyl) benzyl] thio.} acetic [1 J + HSC A nitrostyrene solution (10 g, 0.067 mol) in tetrahydrofuran (250 ml) with mercaptoacetic acid (7.4 g, 5.6 ml, 0.08 mol) followed by pyrrolidine (3 drops). After stirring for two hours the reaction mixture was concentrated on silica gel and chromatographed eluting with 4.1, hexanes: ethyl acetate, to give the title product as a solid (13.14 g, 81% of performance). Analysis: C8H7N02. Calculated: C, 49.78; H, 4.60; N, 5.81%. Found: C, 49.50; H, 4.66; N, 5.81%. Following essentially the same procedure described in Example 1 but using the appropriately substituted nitroetiol compounds the following compounds are obtained: Example Re R7 RT R9 R10 R R1 2 H COLOR / STATE H H H H CH = CH2 H 3 H yellow oil. OCH3 H OCH3 H CH = CH2 H Oil yellow 4 HHHHH C02CH3 H 5 Oil yellow HH CH3 HH CO2C2H5 H 6 Colorless oil HHHHH CO2C2H5 H 7 H Colorless oil HHHH m C02 (CH2) 3CH3 H 8 Colorless oil HHHHH C02 (CH2) 5CH ( CH3) 2 H Colorless oil 9 HHHHH C02CH2CH (C2H5) [(CH2) 3CH3] H Colorless oil 10 MU • IMII CRUG, H Colorless oil 11 HHFHH C02 (CH2) SCH (CH3) 2 H Colorless oil 12 HHFHH H2CH (C2H5) [(CH2) 3CH3] H Colorless oil tfl or C4 ¡• 1 Example R6 Ri R8 R9 R 10 R Ri Color / State 13 1 I. II F II I I C6HS II Colorless Oil 14 I I 11 F 11 I I C2H5 II Colorless Oil 1 I II F II I I CO2CH3 H Oil Colorless 16 I I II F II 1 1 C { ) 2C2} U 11 Colorless Oil 17 1 I H F II 1 I C02 (CII2) 3CH3 II Colorless Oil 18 I I II -OCH2O- 1 I CO2CH3 II Yellow Oil 19 1 I II - CI O- I I CO2C2H5 II Yellow Oil I 1 II -OCH2O- I I C02 (CH2) 3CH3 II Yellow Liquid 21 I I II -OCH2O- I I CO2 (CH2) 5CH (CH3) 2 II Yellow Oil 22 1 1 II -OCH2O- I 1 C02 H2CI 1 (C2? I5) l (CI I2) 3CH31 11 Yellow Oil 23 I I 11 -OCH2O- I 1 c6? I $: II Yellow Oil 24 I I II -OCIhO- I I C2II5 II Yellow Oil 1 I 11 CII3 11 I I II II Color Oil 26 1 I II CII3 II I I H H Colorless Oil 27 1 1 II CII3 II I I H 11 Colorless Oil 28 1 I 11 CII3 11 I I II H Yellow Oil 29 1 I II CII3 11 I I H H Yellow Oil I I II CH II I 1 H H Yellow Oil to o vi CN ¡• 1 example R6 R7 R «RQ R 10 R RI Color / State 31 I 1 11 CH (CII3) 2 H 11 ^ II H \ a ite Yellow 32 I I 11 CH (CH? 2 H II 11 II ceite Yellow 33 I I 11 CH (CH3) 2 H 11 11 II Yellow Oil 34 I I li c? I (cpvh H II II H ceite Yellow I I 11 CH (CH3) 2 II i 11 II II Yellow Oil 36 1 1 11 CH (CH3) 2 II H C6II5 H Yellow Oil 37 I I II CH (C11,) 2 II II C2II5 H Yellow Oil 38 I I 11 CII (CH3) 2 II II CH-CH2 H Yellow Oil 39 I I II II H F C02CH3 H Yellow Oil 40 I 1 11 II li F C02C2II5 11 Oil Yellow 41 I 11 II II F C02 (CH2) 3CH3 H Yellow Oil 42 I 1 11 II II F C02 (CH2) 5CH (CH3) 2 H Yellow Oil 43 I I II 11 II F C02CH2CII (C2H5) [(CH2) 3CH3] H Yellow Oil 44 I 1 II 11 H F C6H5 II Yellow Oil 45 I 1 II II II F C2H5 H Yellow Oil 46 I 1 11 11 II F CH = CH H Yellow Oil 47 I I 11 OCH3 H H C02CH3 H Yellow Oil 48 I I II OCH3 II H C02C2H5 H Yellow Oil «A 10 O vi (N Example R (, R7 Rs R9 R 10 R Ri Color / State 49 II II OCI1, 11 1 I C02 (CII2) 3CH3 II Yellow Oil 50 11 II OCH, II I I C02 (CH2) 5CH (CH3) 2 II Yellow Oil 51 11 11 OCH, II I I CU CH2CH (C2ll5) [(CH2) 3Cíl3] II Yellow Oil 52 II II OCH, 11 I I Cfills 11 Yellow Oil 53 11 II OCH3 II I 1 CzIIj II Yellow Oil 54 11 II OCH3 II 1 I CH = CI-2 II Yellow Oil 55 II II II OCH3 I I C02CH3 H Yellow Oil 56 11 11 II OCII3 1 I CO2C2H5 H Yellow Oil 57 II 11 II OCII3 1 I C02 (CH2) 3CII3 H Yellow Oil 58 11 11 11 OCH3 1 I C? 2 (CH2) sCH (CH3) 2 H Yellow Oil 59 II II II OCII3 j 1 I C02CH2CH (C2ll5) [(CH2) 3cH3] H Yellow Oil 60 II II II OCH3 1 1 C6II5 H Yellow Oil 61 11 11 II OCH3 I 1 C2II5 II Yellow Oil 62 11 II II OCII3 1 I CH = CH2 H Oil Yellow 63 II II F II 1 I C02H H Brown oil 64 II II -OCIhO- I 1 C02II H Brown oil 65 II II CII3 II I I C02II H samásóilicb blancusao 66 11 II CH (CII3) 2 II r i C02II H Brown oil »? t-l or (¡• J Example I < 6 R7 Rs R9 Rio R R. Color / Condition 67 II II II F C02H II Brown oil 68 II II 0C1I3 II C02H II Brown oil 69 11 OCH3 II 11 co2H 11 Brown oil 70 II Cl II II C02CH3 H Yellow oil 71 II Cl II II CO2C2H5 H Yellow Oil 72 II Cl II II C02 (CH2) 3CH3 II Yellow Oil 73 II Cl II II C02 (CH2) 5CH (CH3) 2 II Yellow Oil 74 II Cl II II C02CIl2CH (C2H5) [(CIl2) 3CII3] II Yellow Oil 75 II Cl II II c6p5 H Yellow Oil 76 II Cl II H C2FI5 H Yellow Oil 77 II Cl II II CH = CH2 H Yellow Oil 78 11 Cl II II C02H 11 Yellow Oil 79 II OCH3 H OCH3 CO2CH3 H Yellow 80 II II OCH3 H OCH3 II White 81 II II OCH3 H OCH3 C6 6H "5 H Yellow Wl or ti fN ¡• 4 Example R6 U7 Rß R? RIO R R? Color / Condition c6 H 82 II II II II II GHSCHCH2N02 H White Oil White Yellow Oil Yellow Yellow Oil Yellow Oil Yellow Oil Yellow Oil Yellow Oil Yellow Oil Yellow Oil Yellow Oil Yellow Oil Yellow Semi-Solid Whitish Wt 3 O H f i CN Example RßRv Rs R9 Rio R Ri Color / State 97 II I II II II II CH3 II Oil Yellow 98 II I 1 II CN II CO2CII3 II I-Solide Brown 99 II II II CN 11 CO2C2H5 11 Oil Colorless 100 HII II CN II C02 (CH2) 2CII3 H Oil Colorless 101 II II II CN II C? 2 (CII2) 3CH3 II Color Oil 102 II II OCH3 II 11 C02 (CII2) 2CH3 11 Color Oil 103 II II II OCH3 II C? 2 ( CH2) 2CH3 II Semi-Solid Roasted r ~ 104 II II -OCH2O- HC? 2 (CH2) 2CH3 II Color Oil 105 II II II 11 II C02 (CH2) 2CIl3 II Colorless Oil 106 11 1 1 -OCH2O- II - C02CII2C6H5 H Color Oil 107 II i I II OCII3 II C? 2CII2C6H5 II Color Oil 108 II II OCII3 II II C? 2CH2C6H5 II Color Oil 109 II 1 I -CII = CH-CH = CH- 11 C02H H Semi- Solid Light yellow 110 11 1 I -CH = CH-CH = CH- II CO2CII3 II Light Yellow Oil 111 II i 1 -CH = CH-CH = CH- II C02C2H5 'H Light Yellow Oil 112 II 1 I -C1I = CH-CH = CH- II C02 (CH2) 2CH3 II Light Yellow Oil 113 II 1 I -CII = CH-CH = CH- II C02 (CIl2) 3CII3 H Light Yellow Oil 114 II I 1 -CH = CH-CH = CH-HC? 2CH2C6H5 H Light Yellow Oil Wl or CN A) R6 R7 As Ro Rio R R. Color / State 1 15 II II -CH = CH-GH = CH- II c2n5 II Light Yellow Oil 1 16 II II -CH = CI I-CE = CII- H C6H5 11 Light Yellow Oil 1 17 II OCF3 H C02CH3 11 Light Yellow Oil 1 18 II OCF3 H C02C2II5 II Light Yellow Oil 1 19 11 OCF3 II C02 (CH2) 2CH3 11 Light Yellow Oil 120 II OCF3 II C02 (CH2) 3CH3 II Light Yellow Oil 121 II OCF3 II C02CH2C6H5 II Light Yellow Oil 122 II OCF3 H C2H5 II Light Yellow Oil 00 f) 123 II OCF3 II CH = CH2 II Light Yellow Oil 124 11 OCF3 II C6H5 11 Light Yellow Oil 125 II -CH = CH-CH = CH- CH = CH2 II Solid Light Yellow 126 II II II II c6n5 127 II OCF3 H C02II H Clear colorless substance 128 11 II N02 C02H H Semi Solid Dark Yellow 129 11 II N02 CII = CH2 H Dark Yellow Oil 130 Cl 11 II H Cl CO2II H Semi Solid Colorless 131 Cl II II Cl Cl C02CH3 H Colorless Oil 132 Cl II II Cl Cl C02C2H5 H Colorless Oil -rt or u i H i (N M R10 Ri R «> R ", R Ri Color / State 133 Cl II II 11 Cl C02 (CH2) 2CH3 li Colorless Oil 134 Cl II II 11 Cl C02 (CH2) 3CH3 11 Colorless Oil 135 Cl 11 II II Cl C02CH2C6H5 II Colorless Oil 136 Cl 11 II II Cl C2HS II Light Yellow Oil 137 Cl 11 II II i cl CßHs II Colorless Oil 138 II II II N02! 11 CO2CH3 H Light Yellow Oil 139 F F F F F C02II H Yellow Oil 140 F F F F CO2CH3 H Dark Yellow Oil 141 F F SCH2C02- F F CO2CH3 11 Semi-Solid Yellow CII3 142 F F F F F CO2C2H5 II Oil Yellow 143 F F SCH2CO2- F F C? 2C2II5 II Oil Yellow C2H5 144 F F F F C02 (CH2) 2CH3 II Oil Dark Yellow 145 F F SCII2C02- F F C02 (CH2) 2CH3 H Dark Yellow Oil (CII2) 2CII3 146 F F F F C02 (CH2) 3CH3 H Yellow Oil 147 F F SCH2CO2- F F C02 (CH2) 3CH3 H Yellow Oil Wl O i CN i -i mplo * 6 R 7 Rg R9 Rio R - R? Color / Condition (CH2) 3CH3 148 F 1 1 F F C6Hs H Semi Solid Dark Yellow 149 F SCI LCrlls F F C6H5 H Yellow Oil 150 II 1 11 11 II C02CH3 CH3 Oil Yellow 151 11 1 I I 11 H CO2C2H5 CH3 Oil Yellow 152 11 I F F II C02C113 11 Oil Yellow 153 11 I I F F H CO2C2HS H Yellow Oil 154 11 1 I F F II C02 (CH2) 2C3 H Yellow Oil 155 11 1 1 F F II C02CH (CH3) 2 H Yellow Oil 156 11 11 11 H H H Color Oil V 157 11 I I OCIh H H H Color Oil? _? 158 II H OCH3 H H Color Oil ) r-l H or CN Vi i'J Example R6 R7 R «Rc R 10 R Ri Color / State 159 H H -OCH20- H H Colorless Oil?!) 160 H H H H H H Colorless Oil Y_J Oil Colorless Oil Solid Color Yellow OilYellow Oil Yellow Oil Yellow Oil Yellow Solid Yellow Semi Solid Yellow Solid Yellow wt ST i -l u u CN Example R Color / State 171 CO2CH3 Oil Orange Dark 172 C02C2Hs Oil Light Red 173 C02 (CH2) 3CH3 Oil Orange Light 174 CO2CH2C6H5 Oil Dark Red 175 C2H5 Light Orange Oil 176 CH = CH2 Light Red Oil 177 CeHs Oil Dark Orange 178 C02 (CH2 ) 2CH3 Light Orange Oil 179 C02H Semi-Solid Yellow Cla 4? Example R 6 R Color / State 180 H CH3 Oil Orange 181 H C02H Oil Orange Dark 182 H C02 CH3 Oil Light Yellow 183 H CO2C2H5 Oil Light Yellow 184 H C02 (CH2) 3 CH3 Oil Light Yellow 185 H C02CH2CrHs Oil Light Yellow 186 H C2H5 Liquid Orange Clare 187 H CH = CH2 Clear orange liquid 188 H C5H5 Light orange oil 189 H C02 (CH2) 2CH3 Light yellow oil 190 Br C02H Light brown oil 191 Br C02CH3 Light brown oil Example R Color / State 192 Br C02C2H5 Yellow Oil 193 Br C02 (CH2) 2CH3 Oil Yellow 194 Br C02 (CH2) 3CH3 Oil Yellow 195 Br CßHs Oil Yellow O Example R Color / State 196 C02H Oil Orange Dark 197 C02CH3 Oil Light Yellow 198 CO2C2H5 Oil Light Yellow 199 C02 (CH2) 2CH3 Oil Light Yellow 200 C? 2 (CH2) 3CH3 Oil Light Yellow 201 C2Hd Oil Dark Yellow 202 CH = CH2 Oil Light Yellow 203 CsHs Oil Colorless EXAMPLE 204 l? Nematicidal soil test directed to root knot nematode Meloidogyne incognita in greenhouse tomatoes The test compound was solubilized in acetone and diluted with water to obtain the required test concentration. A 3-inch (2.54 cm) pot with black muddy soil and containing a three-week-old tomato transplant plant was irrigated with the test solution. Four thousand larvae were deposited from the Meloidogyne incognita J2 0 root node in an aqueous suspension on the ground. The sherds were kept in the greenhouse and four weeks after the inoculation of said sherds the roots of the ground plant were freed and the degree of root gall formation was evaluated using the root knot gill formation index which is identified below. The etotrophs are included in the test as an industrial standard. The results are summarized in Table I. gill index of the root knot gall index Percentage of total gills of root system 0 0 1 10 l 2 2 3 3 ~~ 30 4 40 5 50 6 60 7 70 80 90 10 100 0 TABLE I Nematicidal soil evaluations Compound Example 1 50 0 25 0 10 1 Ethoprophos 50 Qi 25 0: 10 o Control 7 Phytotoxicity observed EXAMPLE 205 Evaluation of the test compounds against M. Incognita (nematode of the root knot) The larvae of. Incognita recently emerged were left in a S Medium suspension (saline of regulated pH) up to a concentration of 50-65 worms per 50 μl. 50 μl of the worms suspension was pipetted into microtiter plate wells containing the test compounds. The plates were then covered with plastic plate sealants to reduce the volume loss by evaporation. After 20-24 hours of incubation the larvae were evaluated by movement. Wells containing obviously dead / paralyzed larvae were evaluated as positive. A result of "9" indicates inactive caterpillars with a straight morphology, the type of a rod. A result of "8" indicates inactive caterpillars with a curly or curved flabby morphology. A result of "7" indicates dead / paralyzed caterpillars after 72 hours. The results are summarized in Table II.

Table 11 Nematicidal evaluation of the test compounds Example M. Incognita (150 ppm) 1 9 2 9 3 9 4 9 5 9 6 9 7 9 0 0 10 0 11 0 12 0 13 0 14 0 15 9 16 9 17 9 TABLE II (Cont.) 18 9 19 9 20 9 21 22 0 23 8 24 9 25 9 26 9 lü 27 0 28 9 29 9 30 0 31 9 32 9 33 0 34 0 35 0 36 0 37 0 38 0 0 39 9 40 9 41 9 42 0 43 0 44 0 45 0 TABLE II (Cont.) 47 9 48 9 49 9 50 0 51 0 52 9 53 9 54 9 55 9 56 9 57 9 58 0 59 0 60 0 61 0 62 9 63 9 64 9 65 9 66 9 67 9 68 9 69 9 70 9 71 0 72 0 73 0 74 0 75 0 ABLA II (Cont 76 0 77 o 78 g 79 0 80 0 81 0 82 9 83 9 84 0 85 9 86 0 87 0 88 8 89 90 91 0 92 0 93 0 . 94 0 95 0 96 9 97 0 98 0 99 0 100 0 101 9 102 9 103 9 104 TABLE II (Cont 105 0 106 c 107 or 108 a 109 0 110 0 111 0 112 0 113 0 ?? 114 0 115 0 116 0 117 0 118 0 119 9 120 9 121 122 0 123 0 124 0 125 0 0 127 9 128 9 129 0 130 9 131 9 132 0 133 0 134 0 TABLE II (Cont.) 135 0 136 0 137 or 138 or 171 9 172 9 173 9 174 9 175 9 176 9 177 9 178 _ 9 179 9 181 9 182 9 183 9 184 9 185 9 186 0 187 9 188 9 189 9 196 9 197 9 198 9 199 9 200 9 201 0 202 0 EXAMPLE 206 Evaluation of test compounds against C. eleqans Cultures of C. elegans (Bristol strain from J. Lewis) were plated on e. Coli on plates of .Agar NG at 20 ° C. New crops were established weekly. The test nematodes were removed from the cultures using Na buffer. The compounds were dissolved with 80% acetone. The test material was introduced by icropipette (25 μl) into a single well of a 96-well sterile tissue culture plate and the solvent was allowed to evaporate. A freshly prepared volume (50 'μL) of C. elegans in Na buffer was _introduced by micropipette into each treated well and several well controls were performed per plate. Plates were incubated at 20 ° C. Observations for efficacy were made under a dissecting microscope at 4 and 24 hours after immersion. Immediately before reading the plate it was tapped gently to stimulate the movement of the caterpillars. The activity was judged subjectively, but semiquantitatively based on the effects of the drug on the motility of adults and larvae. The criteria were the following: 9 = complete death after 4 hours, 8 = complete death after 24 hours, 7 = markedly reduced motility in approximately 95 of the caterpillars in 24 hours, and 0 = normal motility the same as the controls. The results are summarized in Table III.

TABLE III Evaluation of test compounds against C. elegans Example Percentage against C, elegans (150 ppm) 1 9 2 0 3 0 4 9 5 9 6 8 7 8 0 9 0 10 0 11 0 12 0 13 0 14 0 15 9 16 17 18 9 19 9 TABLE III (Cont. 20 8 21 0 22 0 23 7 24 8 25 9 26 8 27 0 28 0 29 8 30 0 31 8 32 7 33 7 34 0 35 0 36 0 37 0 38 0 39 9 40 41 7 42 0 43 0 44 7 45 0 46 7 47 9 48 9 TABLE III (Cont 49 Q 50 7 51 0 52 9 53 9 54 9 55 56 57 7 58 0 59 0 60 0 61 7 62 7 63 9 64 9 65 9 66 9 67 9 68 69 9 '70 7 71 7 72 0 73 0 74 0 75 0 76 7 77 0 TABLE III [Cont.] 78 / 79 7 80 7 81 7 82 9 83 9 84 9 85 7 86 0 87 0 89 0 90 7 91 0 92 0 93 0 94 0 95 0 96 9 98 8 99 0 100 8 101 0 102 9 103 104 9 105 9 106 107 108 TABLE III [Cont. ) 109 g 110 111 8 112 9 113 Q 114 115 0 116 0 117 118 119 120 0 121 9 122 8 123 7 124 7 125 0 127 9 128 9 129 0 130 9 131 7 132 0 133 0 134 0 135 0 136 0 137 0 139 9 TABLE III (Cont.) 140 8 141 8 142 8 143 0 144 7 145 0 146. 7 147 0 148 0 ?? 149 0 158 9 171 7 172 173 174 0 175 0 176 0 177 0 178 0 203 9 0 EXAMPLE 207 Insecticidal and acaricidal evaluation of the test compounds. Test solutions were prepared by dissolving the test compound in 35% acetone in a water mixture to give a concentration of 10,000 ppm. Subsequent dilutions were prepared with water as necessary. Spodoptera eridania, second instar larva, Southern skipjack (SAW) One Sieva bean leaf expanded to a length of 7-8 cm was immersed in the test solution with stirring for three seconds and allowed to dry under cover. The leaf was then placed in a 100 x 10 ml petri dish containing a wet filter paper on the bottom and 10 second stage caterpillars. After five days, observations were made about mortality, reduction of feeding or any interference with the normal moult. Diabrotica virgifera virgifera Leconte, rootworm of southern second stage corn. One cm3 of fine talc was placed in a wide-mouthed screw-cap glass jar. Pipette 1 ml of the appropriate acetone assay solution onto the talc to provide 1.25 mg of the active ingredient per jar. The jars were left under a gentle air flow until the ketone was evaporated. The dried talc was loosened, one cm3 of millet seed was added, which served as food for the insects, and 25 ml of wet soil was added to each jar. The jar was covered and the contents mixed thoroughly mechanically. Following this 10 worms were added from the root of the second stage to each of the jars and then the jars were capped without adjusting to allow air exchange for the larvae. The treatments were followed for five days until the mortality counts were made. The missing larvae were assumed dead because they decompose rapidly and can not be found. The concentrations of active ingredient * used in this test correspond to approximately 50 kg / ha. Tetranychus urticae (OP resistant strain), spider mite spots (TSM) Sieva beans with primary leaves expanded to 7-8 cm were selected and cut until one plant per pot was left. A small piece of an infested leaf taken from the main colony was cut and placed on each leaf of the test plant. This was done about 2 hours before treatment to allow the mites to move over the test plant and deposit eggs. The cut size of the infested leaf was varied to obtain approximately 100 mites per leaf.

At the time of the test treatment the piece of leaf used to transfer the mites was removed and discarded. The newly infested plants were immersed in the test solution for three seconds with agitation and left under cover to dry. After two days a leaf was removed and mortality counts were made. Aphis gossypii, cotton aphid (CA) Cotton plants in the cotyledon stage were selected and cut so that one plant per pot would remain. A heavily infested leaf was taken from the main colony and placed on top of each cotyledon. The aphids were allowed to transfer to the host plant overnight. At the time of the test treatment the leaf used to transfer the aphids was extracted and discarded. The cotyledons were immersed in the test solution and allowed to dry. After five days the mortality counts dried up. Spodoptera eridania, southern scoria eggs and Diabrotica undecimpunctata, southern corn rootworm eggs (SAW eggs) and (SCR eggs). The wells containing the artificial diet were treated with the test solutions and dried. The eggs of the appropriate insect were then placed in the wells. The wells were covered with ventilated adhesive transparent plastic covers. After 7 days the mortality counts were made. The tests were averaged according to the scale shown below and the data obtained are shown in Table IV.

Evaluation table 0 = no effect 5 = 56-65% death 1 = 10-25% death 6 = 66-75% death 2 = 26-35% death 7 = 76-85% death 3 = 36-45% of death 8 = 86-99% of death 4 = 46-55% of death 9 = 100% of death TABLE IV Insecticidal and acaricidal evaluations of the SAW SCR test compounds CA SAW Eggs Eggs TSM WCR Ex (3001) (3001) (3001) (10001) (3001) (501) 1 0 0 2 0 0 - 3 0 0 4 5 0 0 0 0 4 0 0 0 0 0 4 6 0 0 0 0 7 7 0 0 0 0 0 8 0 0 0 0 0 9 • 0 0 0 0 4 0 or - 0 0 0 11 0 0 0 0 12 0 or 0 0 0 13 7 or 0 0 0 14 0 or 0 0 0 15 0 or 0 0 0 3 16 0 0 0 0 0 17 0 0 0 5 18 9 or 0 0 0 0 19 0 or 0 0 0 0 3 0 0 0 0 0 21 7 or 0 0 0 0 22 0 or 0 0 0 0 23 4 or 8 9 9 0 4 24 0 0 0 0 0 25 0 or 0 9 0 0 9 , -chloridity ppm SAW SCR CA SAW Eggs Eggs TSM WCR - (3001) (3001) (3001) (10001) (3001) (501) 26 0 0 0 0 0 7 7 4 0 9 9 0 * > 28 0 0 9 0 0 8 29 4 5 9 0 0 0 0 0 9 0 0 7 31 0 0 0 0 0 32 0 0 0 0 0 33 0 0 0 0 2 34 0 5 9 3 0 0 0 9 3 0 36 0 1 7 0 0 37 0 0 0 0 0 38 0 0 9 0 0 39 0 4 0 0 8 40 0 3 0 0 9 41 0 1 0 0 9 42 0 0 9 0 6 43 0 4 9 0 7 44 0 5 0 0 4 45 0 0 7 0 8 46 0 1 0 0 9 47 0 0 0 0 4 4 48 0 0 0 0 0 0 49 0 0 0 0 0 0 50 0 0 9 0 0 0 51 0 0 9 8 0 4 52 0 0 0 0 0 4 53 0 4 0 0 0 0 54 0 0 0 0 0 5 55 0 4 0 0 0 0 56 0 0 0 0 5 0 57 0 0 0 0 0 0 58 0 0 0 0 0 0 59 0 0 0 0 0 0 60 0 0 0 0 0 0 61 5 0 0 0 0 0 62 5 0 0 0 0 0 63 0 0 0 0 64 0 0 9 0 65 0 0 0 9 66 0 0 0 8 67 0 0 0 9 TABLE IV (cont.) SAW SCR CA SAW Eggs Eggs TSM WCR Ex. (3001) (3001) (3001) (10001) (3001) (501) 68 0 0 0 69 0 0 0 0 70 0 0 0 0 71 0 0 0 or 72 0 0 0 or 73 0 0 0 or 74 0 0 0 or 75 0 0 0 or 76 0 0 0 or 77 0 0 3 or 78 0 0 0 or 88 0 0 0 0 or 89 0 0 0 or o 90 0 0 0 or 91 0 0 0 or o 92 0 0 0 or 5 93 0 0 0 or o 94 0 0 0 or o 95 0 0 0 or 4 96 0 0 0 o O 98 0 5 0 0 3 or 99 0 0 0 0 0 or 100 0 0 0 0 0 or 101 0 0 0 0 or o 102 0 0 0 0 or o 1Q3 0 0 0 0 4 or 104 0 0 0 0 0 or 105 0 3 0 0 or 3 106 0 0 0 0 or o 107 0 0 0 0 or o 108 0 0 9 0 or o 109 0 0 0 0 or o 110 0 0 0 0 or o 111 0 0 8 0 or o 112 0 0 8 0 or o 113 0 3 9 0 or o 114 0 0 9 0 3 or 115 0 0 8 0 0 or 11b 0 0 0 0 o o 117 0 0 0 0 or o 118 0 0 9 0 o o TABLE TV (cont.) SAW SCR R CA SAW Eggs Eggs TSM WC Ex. (3001) (3001) (3001) (10001) (3001) (501) 0 ü 6 162 0 171 0 0 0 0 0 0 172 0 0 0 0 0 0 173 0 0 0 0 0 0 174 0 0 0 0 0 0 175 0 0 0 0 0 0 176 0 0 0 0 0 0 177 0 0 0 0 0 0 lü 178 0 0 0 0 0 0 179 0 0 0 0 0 0 181 0 0 9 0 0 0 182 0 0 0 0 0 0 183 0 0 0 0 0 0 184 0 0 9 0 0 0 185 0 0 0 0 0 0 186 0 4 0 0 0 4 187 0 0 0 0 0 0 188 0 0 0 0 0 3 189 0 0 0 0 0 0 190 0 0 0 0 0 0 191 0 0 0 0 0 0 192 0 0 0 0 0 0 193 0 0 0 0 0 0 194 0 0 0 0 0 0 195 0 0 0 0 0 0 196 0 0 0 0 0 9 0 197 5 0 9 0 0 0 198 0 0 9 0 0 7 199 0 0 9 0 .0 8 200 0 0 9 0 0 4 201 0 0 0 0 0 7 202 0 0 9 0 0 9 203 0 0 9 9 0 8 It is noted that in relation to this date, the best method known by the applicant to carry out the aforementioned invention, is the conventional one for the manufacture of the objects or products to which it refers .

Claims

CLAIMS Having described the invention as above, the content of the following claims is claimed as a priority:

1. A method for the control of parasites or pests of helminths, nematodes, insects or acarids characterized in that it comprises contacting said pests or parasites or their provision of food, habitat or breeding places with a pesticidally or parasiticidally effective amount of a compound having the structural formula I wherein Ar is phenyl optionally substituted with any combination of 1 to 5 halogen atoms, one or two cyano groups, one or two nitro groups, one to three C? -C alkyl groups, one to three C? ~ C haloalkyl groups , one to three C alco-C 4 alkoxy groups, one to three C 1 -C 4 haloalkoxy groups, one to three C 1 -C 4 alkylthio groups, one to three haloalkylthio C? ~C groups, a benzylthio group or a SCH 2 CO 2 R 2 / lo group 2-naphthyl optionally substituted with any combination of 1 to 5 halogen atoms, one or two "cyano groups, one or two nitro groups, one to three C1-C4 alkyl groups, one to three C1-C4 haloalkyl groups one to three groups C 1 -C 4 alkoxy, one to three C 1 -C 4 haloalkoxy groups, one to three C 1 -C 4 alkylthio groups, one to three C 1 -C 4 haloalkyl groups, piperonyl optionally substituted with any combination of 1 to 3 halogen atoms, one or two cyano groups, one or two nitro groups, one to three C1-C4 alkyl groups, one to three C1-C4 haloalkyl groups, one to three groups C 1 -C 4 alkoxy, one to three C 1 -C 4 haloalkoxy groups, one to three C 1 -C 4 alkylthio groups, one to three C 1 -C 4 halo-alkylthio groups, 2-, 3-. or 4-pyridyl optionally substituted with any combination of 1 to 4 halogen atoms, one or two cyano groups, one or two nitro groups, one to three C1-C4 alkyl groups, one to three C: -C4 haloalkyl groups, one to three C1-C4 alkoxy groups, one to three C1-C4 haloalkoxy groups, one to three alkylthio d-C4 groups, one to three C1-C4 halo-alkylthio, 2- or 3-furyl groups optionally substituted with any combination of 1 to 3 halogen atoms, one or two cyano groups, one or two nitro groups, one to three C? -C4 alkyl groups, one to three C? -C4 haloalkyl groups, one to three C1-C4 alkoxy groups, one to three C1-C4 haloalkoxy groups, one to three C1-C4 alkylthio groups, one to three haloalkyl groups C? -C4 2- or 3-thienyl optionally substituted with any combination of 1 to 3 halogen atoms, one or two groups cyano, one or two nitro groups, one to three C? -C4 alkyl groups / one to three C? -C4 haloalkyl groups, one to three C1-C4 alkoxy groups, one to three C1 haloalkoxy groups -C4, one to three C1-C4 alkylthio groups, one to three C1-C4 halo-alkylthio groups, R is hydrogen, C02R3, C (0) NR4R5, (CH2) nCR; (NR4R5) COiR ^, __CH (OR5) CH0R7, CH (CH20R8) SCH (R9) CH2N02, Ci-C_ alkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C_-C4 haloalkenyl, phenyl optionally substituted with any combination from one to five halogen atoms, one or two cyano groups, one or two nitro groups, one to three C1-C4 alkyl groups, one to three C1-C4 haloalkyl groups, one to three C1-C4 alkoxy groups, one to three C1-C4 haloalkoxy groups, one to three C1-C4 alkylthio groups, one to three C1-C4 haloalkyl groups, 2- or 3-furyl optionally substituted with any combination of 1 to 3 halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups one to three C 1 -C 4 alkoxy groups, one to three C 1 -C 4 haloalkoxy groups, one to three C1-6 alkylthio groups C4, one to three haloalkyl groups C? -C4 / 2- or 3-thienyl optionally substituted with any combination of 1 to 3 halogen atoms, one or two cyano groups, one or two nitro groups, one to three C? -C alkyl groups / one to three C1-C4 haloalkyl groups, one to three C1-C4 alkoxy groups, one to three C1-C4 haloalkoxy groups, one to three C? -C4 alkylthio groups / one to three C1-C4 haloalkylthio groups, R, Rβ R7 and Rs are each independently hydrogen or C? -C6 alkyl; m is 0, 1 or 2; n is 0? 1; R9 is phenyl optionally substituted with any combination of 1 to 5 halogen atoms, one or two cyano groups, one or two nitro groups, one to three C1-C4 alkyl groups, one to three C1-C4 haloalkyl groups, one to three groups C1-C4 alkoxy, one to three C1-C4 haloalkoxy groups, one to three C1-C4 alkylthio groups, one to three C1-C4 haloalkyl groups, R3 is hydrogen, C1-C10 alkyl CH (haloalkyl C? -C? c) , C3-C10 alkenyl, C3-C10 haloalkenyl, a benzyl cation optionally substituted on the ring with any combination of 1 to 5 halogen atoms, one or two cyano groups, one or two nitro groups, one to three C1-C4 alkyl groups , one to three C1-C4 haloalkyl groups one to three C1-C4 alkoxy groups, one to three C1-C4 haloalkoxy groups, one to three C1-C4 alkylthio groups, one to three C4-4 haloalkylthio groups, or optionally substituted phenyl with any combination of 1 to 5 halogen atoms, one or two cyano groups, one or two nitro groups, one to three C1 alkyl groups -C4, one to three C1-C4 haloalkyl groups, one to three C1-C4 alkoxy groups, one to three C4-4 haloalkoxy groups, one to three C1-C4 alkylthio groups, one to three C1-C4 haloalkyl groups, R4 and R5 are each independently hydrogen, C1-C10 alkyl, CH2 (C1-C10 haloalkyl), Cj-Clu alkenyl, C3-C10 haloalkenyl, benzyl optionally substituted on the ring with any combination of one to five halogen atoms, one or two cyano groups, one or two nitro groups, one to three C1-C4 alkyl groups, one to three C1-C4 haloalkyl groups, one to three C1-C4 alkoxy groups, one to three C1-C4 haloalkoxy groups, one to three groups C 1 -C 4 alkylthio, one to three C 1 -C 4 haloalkylthio groups, or phenyl optionally substituted with any combination of 1 to 5 halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups, one to three C 1 -C haloalkoxy groups, one to three C 1 -C 4 alkylthio groups, one to three C1-C4 haloalkylthio groups, and when R4 and R5 are taken together with the atom to which they are attached, they can form a one or six member ring where R4Rs is represented by: - (CH _), -, - (CH2 ) so- (CH2) 2? (CH2) 2-; and Ri is hydrogen, C1-C4 alkyl, or phenyl optionally substituted with any combination of 1 to 5 halogen atoms, one or two cyano groups, one or two nitro groups, one to three Cj.-C alkyl groups one to two C1-C4 haloalkyl groups, one to three C1-C4 alkoxy groups, one to three C1-C4 haloalkoxy groups, one to three C1-C4 alkylthio groups, one to three C1-C4 haloalkyl groups,

2. The method according to claim 1, characterized in that the compound is selected from the group consisting of:. { [alpha- (-nitromethyl) benzyl] thio} methyl acetate; acid { [alpha- (Nitromethyl) benzyl] thio} acetic acid; . { [p-methyl-alpha- (nitro ethyl) benzyl] thio} ethyl acetate; . { [alpha- (Nitromethyl) benzyl] thio} acetate of butilo; . { 3,4- (methylenedioxy) -alpha- (nitromethyl) encyl] thio} methyl acetate; . { 3,4- (methylenedioxy) -alpha- (nitromethyl) encyl] thio} ethyl acetate; . { 3, 4- (methylenedioxy) -alpha- (nitromethyl) encyl] thio} acetate of butilo; . { [p-methyl-alpha- (nitromethyl) benzyl] thio} methyl acetate; . { [p-methyl-alpha- (nitromethyl) encyl] thio} acetate of butilo; . { [o-fluoro-alpha- (nitromethyl) benzyl] thio} methyl acetate; . { [o-fluoro-alpha- (nitromethyl) benzyl] thio} ethyl acetate; . { [o-fluoro-alpha- (nitromethyl) encyl] thio} acetate of butilo; . { [p-methoxy-alpha- (nitromethyl) benzyl] thio} methyl acetate; . { [p-methoxy-alpha- (nitromethyl) benzyl] thio} ethyl acetate; . { [p-methoxy-alpha- (nitromethyl) benzyl] thio} acetate of butilo; p- [1- (allylthio) -2-nitroethyl] anisole; . { [m-methoxy-alpha- (nitromethyl) benzyl] thio} - methyl acetate; . { [m-methoxy-alpha- (nitromethyl) benzyl] thio} ethyl acetate; acid. { [p-fluoro-alpha- (nitromethyl) benzyl] thio} acetic; acid { [3, 4- (methylenedioxy) -alpha- (nitromethyl) benzyl + thio} -acetic; acid { [2-nitro-l- (p-tolyl) ethyl] thio} acetic acid; acid { [p-isopropyl-alpha- (nitromethyl) benzyl] thio} acetic; acid { [o-fluoro-alpha- (nitromethyl) benzyl] thio} acetic; acid { [m-methoxy-alpha- (nitromethyl) benzyl] thio} acetic acid { [p-methoxy-alpha- (nitromethyl) benzyl] thio} acé ico; acid { [p-chloro-alpha- (nitromethyl) benzyl] thio} acetic 2,3-bis. { [alpha- (Nitromethyl) benzyl] thio} -1-propanol; 3-. { [alpha- (Nitromethyl) benzyl] thio} to the girl; acid { [2-nitro-l- (2-thienyl) ethyl] thio} acetic; . { [2-nitro-l- (2-thienyl) ethyl] thio} ethyl acetate; 2- [1- (allylthio) -2-nitroethyl] thiophene; and 3- [1-allylthio) -2-nitroethyl] pyridine; among others. . { [alpha- (Nitromethyl) benzyl] thio} methyl acetate; acid { [alpha- (nitrometi-1) benzyl] thio} acetic; • { [p-methyl-alpha- (nitromethyl) benzyl] thio} ethyl acetate; . { [3,4- (methylenedioxy) -alpha -. (Nitromethyl) benzyl] -thio} ethyl acetate; . { [p-methyl-alpha- (nitromethyl) benzyl] thio} methyl acetate; acid { [p-methoxyl-alpha- (nitromethyl) benzyl] thio} ethyl acetate; acid { [p-fluoro-alpha- (nitromethyl) benzyl] thio} acetic; acid { [3, 4- (methylenedioxy) -alpha- (nitromethyl) benzyl] -thio} acetic acid, {. [2-nitro-l- (p-tolyl) ethyl} acetic acid, {. [p-isopropyl-alpha- (nitromethyl) benzyl] thio} acetic acid; . [o-Fluoro-alpha- (nitromethyl) benzyl] thio.) acetic acid; {. [m-methoxy-alpha- (nitromethyl) benzyl] thio.} acetic acid; acid { [p-methoxy-alpha- (nitromethyl) benzyl] thio} acetic; 2, 3-bis. { [alpha- (Nitromethyl) benzyl] thio} -1-propanol; and 3-. { [al'fa- (nitromethyl) benzyl] thio} to the girl; among others.

3. The method according to claim 1, characterized in that the compound is selected from the group consisting of. { [alpha- (Nitromethyl) benzyl] thio} methyl acetate; acid { [alpha- (Nitromethyl) benzyl] thio} acetic,. { [p-methyl-alpha- (nitromethyl) benzyl] thio} ethyl acetate; . { [3,4- (methylenedioxy) -alpha- (nitromethyl) benzyl] -thio} ethyl acetate; . { [p-methyl-alpha- (nitromethyl) benzyl] thio} methyl acetate; _acid. { [p-methoxyl-alpha- (nitromethyl) benzyl] thio} ethyl acetate; acid { [p- fluor-alpha- (nitromethyl) benzyl] thio} acetic; acid { [3, 4- (methylenedioxy) -alpha- (nitromethyl) benzyl] -thio} acetic; acid { [2-nitro-l- (p-tolyl) ethyl} acetic; acid { [p-isopropyl-alpha- (nitromethyl) benzyl] thiojacetic; acid { [o-fluoro-alpha- (nitromethyl) benzyl] thio} acetic; acid { [m-methoxy-alpha- (nitromethyl) benzyl] thio} acetic acid { [p-methoxy-alpha- (nitromethyl) benzyl] thio} acetic 2,3-bis. { [alpha- (Nitromethyl) benzyl] thio} -1-propanol; and 3-. { [alpha- (Nitromethyl) benzyl] thio} to the girl; among others.

4. A method for the protection of crop plants against infestation or attack caused by pests of nematodes, insects or acarids characterized in that it comprises applying to the foliage of the plants or to the soil or water in which they grow a pesticidally effective amount of a compound that has the structural formula I NO, (the) where Ar, m, R and Ri are as described in claim 1.

5. The method according to claim 4, characterized in that the compound is selected from the group consisting of:. { [alpha- (nitromethyl) benzyl] uncle} methyl acetate; acid { [alpha- (Nitromethyl) benzyl] thio} acetic acid; . { [p-methyl-alpha- (nitromethyl) benzyl] thio ethyl acetate; . { [alpha- (Nitromethyl) benzyl] thio} acetate of butilo; . { 3,4- (methylenedioxy) -alpha- (nitromethyl) benzyl] thio} methyl acetate; . { 3,4- (methylenedioxy) -alpha- (nitromethyl) benzyl] thio} ethyl acetate; . { 3,4- (methylenedioxy) -alpha- (nitromethyl) benzyl] thio} acetate of butilo; . { [p-methyl-alpha- (nitromethyl) benzyl] thio methyl methyl acetate; . { [p-methyl-alpha- (nitromethyl) benzyl] thio} acetate of butilo; . { [o-fluoro-alpha- (nitromethyl) benzyl] thio} methyl acetate; . { [o-fluoro-alpha- (nitromethyl) benzyl] thio} ethyl acetate; . { [o-fluoro-alpha- (nitromethyl) benzyl] thio} acetate of butilo; . { [p-methoxy-alpha- (nitromethyl) benzyl] thio} methyl acetate; . { [p-methoxy-alpha- (nitromethyl) benzyl] thio} ethyl acetate; . { [p-methoxy-alpha- (nitromethyl) benzyl] thio} acetate of butilo; p- [1- (allylthio) -2-nitroethyl] anisole; . { [m-methoxy-alpha- (nitromethyl) encyl] thio} methyl acetate; . { [m-methoxy-alpha- (nitromethyl) benzyl] thio} -ethyl acetate; acid { [p-fluoro-alpha- (nitromethyl) benzyl] thio} acetic; acid { [3, 4- (methylenedioxy) -alpha- (nitromethyl) benzyl + thio} -acetic; acid { [2-nitro-l- (p-tolyl) ethyl] thio} acetic acid; acid { [p-isopropyl-alpha- (nitromethyl) benzyl] thio} acetic; acid { [o-fluoro-alpha- (nitromethyl) benzyl] thio} acetic; acid { [m-methoxy-alpha- (nitromethyl) benzyl] thio} acetic; acid { [p-methoxy-alpha- (nitromethyl) benzyl] thio-} acetic; acid { [p-chloro-alpha- (nitromethyl) benzyl] thio} acetic; 2, 3-bis. { [alpha- (Nitromethyl) benzyl] thio} -1-propanol; 3- . { [alpha, - (nitromethyl) benzyl] thio} to the girl; acid { [2-nitro-l- (2-thienyl) ethyl] thio} acetic; . { [2-nitro-l- (2-thienyl) ethyl] thio} ethyl acetate; 2- [1- (allylthio) -2-nitroethyl] thiophene; and 3-Allylthio) -2-nitroethyl] pyridine.

6. A method for treating, controlling, preventing or protecting a warm-blooded animal or fish against helminth infection or infection characterized in that. comprises administering orally, topically or parenterally to said animal or fish an anthelminthically effective amount of a compound having the structural formula I NO, (i) where Ar, m, R and Ri are as described in claim 1.

7. A composition for the control of parasites or pests, helminths, nematodes, insects or acarids characterized in that it comprises an agronomically or pharmaceutically acceptable carrier or a pesticidally or parasiticidally effective amount of a compound having the structural formula I N02 (I). where Ar, m, R and R 'are as described in claim 1.

8. The composition according to claim 7, characterized in that the compound is selected from the group consisting of:. { [alpha- (Nitromethyl) benzyl] thio} methyl acetate; acid { [alpha- (Nitromethyl) benzyl] thio} acetic acid; . { [p-methyl-alpha- (nitromethyl) benzyl] thio} ethyl acetate; . { [alpha- (Nitromethyl) benzyl] thio} acetate of butilo; . { 3,4- (methylenedioxy) -alpha- (nitromethyl) benzyl] thio} methyl acetate; . { 3,4- (methylenedioxy) -alpha- (nitromethyl) benzyl] thio} ethyl acetate; ' { 3, 4- (me, tilendiioxy) -alpha- (nitromethyl) benzyl] thio} acetate of butilo; . { [p-methyl-alpha- (nitromethyl) benzyl] thio} methyl acetate; . { [p-methyl-alpha- (nitromethyl) benzyl] thio} acetate of butilo; . { [o-fluoro-alpha- (nitromethyl) benzyl] thio} methyl acetate; . { [o-fluoro-alpha- (nitromethyl) benzyl] thio} ethyl acetate; . { [o-fluoro-alpha- (nitromethyl) benzyl] thio} acetate of butilo; . { [p-methoxy-alpha- (nitromethyl) benzyl] thio} methyl acetate; . { [p-metQxi-alpha- (nitromethyl) encyl] thio} ethyl acetate; . { [p-methoxy-alpha- (nitromethyl) benzyl] thio} acetate of butilo; p- [1- (allylthio) -2-nitroethyl] anisole; . { [m-methoxy-alpha- (nitromethyl) benzyl] thio} methyl acetate; . { [m-methoxy-alpha- (nitromethyl) benzyl] thio} -ethyl acetate; acid { [p-fluoro-alpha- (nitromethyl) benzyl] thio} acetic acid { [3, 4- (methylenedioxy) -alpha- (nitromethyl) benzylthio} -acetic; acid { [2-nitro-l- (p-tolyl) ethyl] thio} acetic acid; acid { [p-isopropyl-alpha- (nitromethyl) benzyl] thio} acetic; acid { [o-fluoro-alpha- (nitromethyl) benzyl] thio} acetic; acid { [m-methoxy-alpha- (nitromethyl) benzyl] thio} acetic; acid { [p-methoxy-alpha- (nitromethyl) benzyl] thio} acetic; acid { [p-chloro-alpha- (nitromethyl) benzyl] thio} acetic; 2, 3-bis. { [alpha- (Nitromethyl) benzyl] thio} -1-propane1; 3- . { [alpha- (nitromethyl) benzyl] uncle} to the girl; acid { [2-nitro-l- (2-thienyl) ethyl] thio} acetic; . { [2-nitro-l- (2-thienyl) ethyl] thio} ethyl acetate; 2- [1- (allylthio) -2-nitroethyl] thiophene; and 3- [1-allylthio) -2-nitroethyl] pyridine.

9. A compound characterized in that it has the structural formula (the) in the range Ar is phenyl optionally substituted with any combination of 1 to 5 halogen atoms, one or two cyano groups, one or two nitro groups, one to three alkyl groups Cj, -C4, one to three haloalkyl groups C? -C4 , one to three C1-C4 alkoxy groups, one to three C1-C4 haloalkoxy groups, one to three C1-C4 alkylthio groups, one to three halo-alkylthio groups C? -C4 a benzylthio group or a SCH2C02R2 or 2-naphthyl group optionally substituted with any combination of 1 to 5 halogen atoms, one or two groups, one or two nitro groups, one to three d-C4 alkyl groups one to three C1-C4 haloalkyl groups, one to three C? -C, one to three C1-C4 haloalkoxy groups, one to three C1-C4 alkylthio groups, one to three haloalkyl groups C? -C4, piperonyl optionally. substituted with any combination of 1 to 3 halogen atoms, one or two cyano groups, one or two nitro groups, one to three C? -C4 alkyl groups / one to three C1-C4 haloalkyl groups, one to three C2 alkoxy groups .-C4, one to three haloalkoxy groups C? ~ C4, one to three C1-C4 alkylthio groups, one to three haloalkyl groups C1-C4, 2-, 3- or 4-pyridyl optionally substituted with any combination of 1 to 4 halogen atoms, one or two cyano groups, one or two nitro groups, one to three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups, one to three groups C1-C4 haloalkoxy, one to three Ci-C alkylthio groups, one to three haloalkyl groups C 1 -C 4, 2- or 3-furyl optionally substituted with any combination of 1 to 3 halogen atoms, one or two groups cyano, one or two nitro groups, one to three C1-C4 alkyl groups, one to three Ci-C haloalkyl groups, one to three C1-C4 alkoxy groups, one to three C?-C4 haloalkoxy groups, one to three C1-C4 alkylthio groups, one to three haloalkyl groups C1-C4, 2- or 3-thienyl optionally substituted with any combination of 1 to 3 halogen atoms, one or two cyano groups, one or two nitro groups, one a three C 1 -C 4 alkyl groups, one to three C 1 -C 4 haloalkyl groups, one to three C 1 -C 4 alkoxy groups, one to three C 1 -C 4 haloalkoxy groups, one to three C 1 -C 4 alkylthio groups, one to three groups halo-alkylthio Cj.-C4, R is hydrogen, C02R3, C (0) NR4R5 / (CH2) nCR2 (NR4R5) CCsR, ,, CH (0R6) CH2OR7, CH (CH20R8) SCH (R9) CH2N02, Ci- C, C 1 -C 4 haloalkyl, C 2 -C alkenyl, C 2 -C haloalkenyl, phenyl optionally substituted with any combination of one to five halogen atoms, one or two cyano groups, one or two nitro groups, one to three C alkyl groups ? C4, one to three C? -C4 haloalkyl groups, one to three C? -C4 alkoxy groups, one to three C? -C haloalkoxy groups, one to three C1-C4 alkylthio groups, or one to three C1 haloalkylthio groups -C4, 2- or 3-furyl optionally substit with any combination of 1 to 3 halogen atoms, - one or two cyano groups, one or two nitro groups, one to three C1-C4 alkyl groups, one to three C1-C4 haloalkyl groups, one to three C1-6 alkoxy groups C4, one to three C1-C4 haloalkoxy groups, one to three C1-C4 alkylthio groups, one to three haloalkyl groups C? ~ C4, 2- or 3-.thienyl optionally substituted with any combination of 1 to 3 carbon atoms halogen, one or two cyano groups, one or two nitro groups, one to three C? -C4 alkyl groups, one to three C? -C4 haloalkyl groups, one to three C1-C4 alkoxy groups, one to three haloalkoxy C groups? -C4, one to three C1-C4 alkylthio groups, one to three C1-C4 haloalkylthio groups, R2, Rβ7 and Rs are each independently hydrogen or C?-C6 alkyl; m is 0, .1 or 2; n is 0 or 1; R9 is phenyl optionally substituted with any combination of 1 to 5 halogen atoms, one or two graphs cyano, one or two nitro groups, one to three C1-C4 alkyl groups, one to three C1-C4 haloalkyl groups, one a three C1-C4 alkoxy groups, one to three C4-C4 haloalkoxy groups, one to three CX-C alkylthio groups, one to three haloalkylthio groups Cj.-C, R3 is hydrogen, C1-C10 alkyl, CH2 (haloalkyl C- C;), C3-C10 alkenyl C3-C10 haloalkenyl, a benzyl cation optionally substituted on the ring with any combination of 1 to 5 halogen atoms, one or two cyano groups, one or two nitro groups, one to three C1 alkyl groups -C4, one to three C1-C4 haloalkyl groups, one to three C? -C4 alkoxy groups / one to three C1-C4 haloalkoxy groups, one to three C? -C4 alkylthio groups, one to three C1-C4 haloalkyl groups, or phenyl optionally substituted with any combination of 1 to 5 halogen atoms, one or two cyano groups, one or two nitro groups, one to three alkyl groups C1-C4, one to three C1-C4 haloalkyl groups, one to three C?-C4 alkoxy groups, one to three Cj.-C4 haloalkoxy groups, one to three Cilt-C4 alkylthio groups / one to three C1-haloalkylthio groups C4, R4 and R5 are each independently hydrogen, C1-C10 alkyl, CH2 (C1-C10 haloalkyl), C3-C3 alkenyl, C3-C10 haloalkenyl benzyl optionally substituted on the ring with any combination of one to five carbon atoms. halogen, one or two cyano groups, one or two nitro groups, one to three C1-C4 alkyl groups, one to three C? -C haloalkyl groups one to three C? -C4 alkoxy groups one to three haloalkoxy C? , one to three alkylthio groups Gi-C, one to three haloalkylthio groups C1-C4, or phenyl optionally substituted with any combination of 1 to 5 halogen atoms, one or two cyano groups, one or two nitro groups, one to three C1-C4 alkyl groups, one to three C1-C4 haloalkyl groups, one to three C1-C4 alkoxy groups, one to three C1-C4 haloalkoxy groups, one to three C1-C alkylthio groups 4, one to three C1-C4 haloalkylthio groups, and when R4 and R5 are taken together with the atom to which they are attached, they can form a one to six member ring where R4R5 is represented by: - (CH;) -, ( CH 5- or - (CH 2) 20 (CH 2) 2-; and Ri is hydrogen, C1-C4 alkyl, or phenyl optionally substituted with any combination of 1 to 5 halogen atoms, one or two cyano groups, one or two nitro groups, one to three C?-C4 alkyl groups, one to three C? -C4 haloalkyl groups, one to three C? -C alkoxy groups, one to three C? -C4 haloalkoxy groups, one to three C1-C4 alkylthio groups, one to three C1-C4 haloalkyl groups, and with the proviso that Ar is other than phenyl optionally substituted with any combination of one to three halogen atoms, one or two nitro groups, one or two cyano groups, one or three C1-C4 alkyl groups, one to three C1- haloalkyl groups C4, one to three-C1-C4 alkoxy groups, or one to three C1-C4 haloalkoxy groups when R is: (1) C02R3 and R3 is hydrogen or C1-C10 alkyl, (2) C ^ -CI alkyl, O ( 3) phenyl optionally substituted with one to five halogen atoms.

10. The compound according to claim 9, characterized in that it is selected from the group consisting of:. { 3,4- (methylenedioxy) -alpha- (nitromethyl) benzyl] thio} methyl acetate; . { 3,4- (methylenedioxy) -alpha- (nitromethyl) benzyl] thio} ethyl acetate; . { 3 / 4- (methylenedioxy) -alpha- (nitromethyl) benzyl] thio} acetate of butilo; acid { [3, 4- (methylenedioxy) -alpha- (nitromethyl) benzyl] thio} -acetic; 2,3-bis. { [alpha- (Nitromethyl) benzyl] thio} -1-propanol; 3 . { [alpha- (Nitromethyl) benzyl] thio} Alanine, acid. { [2-Nitro-1- (2-thienyl) ethyl] thio} acetic; . { [2-nitro-l- (2-thienyl) ethyl] thio} ethyl acetate; 2- [1- (allylthio) -2-nitroethyl] thiophene; and 3- [1-allylthio) -2-nitroethyl] pyridine.