WO2003029188A2

WO2003029188A2 - Beta-substituted nitrostyrene and cyanostyrene compounds and their use as nematicides and fungicides

Info

Publication number: WO2003029188A2
Application number: PCT/EP2002/010759
Authority: WO
Inventors: John F. Chiarello; Terence J. Bentley; William W. Wood
Original assignee: Basf Aktiengesellschaft
Priority date: 2001-09-26
Filing date: 2002-09-25
Publication date: 2003-04-10
Also published as: WO2003029188A3; AU2002338788A1

Abstract

The present invention describes pesticidal β-substituted nitrostyrene and cyanostyrene compounds having the formula I: wherein A,Ar,R,R1,Y,X,k,l, and m are as defined herein. The present invention is directed to compositions that include compounds of formula (I) and a carrier. Moreover, the present invention relates to methods for protecting crops from attack by nematodes by treating the crop with a pesticidally effective amount of the compound of formula (I). In addition, the present invention includes methods for controlling fungus and/or nematodes by treating the target species with a pesticidally effective amount of the compound of Formula (I).

Description

.NEMATICIDAL AND FUNGICIDAL β-SUBSTITUTED DIHYDRONITROSTYRENE AND DIHYDROCYANOSTYRENE COMPOUNDS AND THEE? USE AS NEMATICIDES AND FUNGICIDES.

The present invention relates to pesticidal compounds, compositions and their methods of use, in particular, the present invention relates to β-substituted dihydronitrostyrene and dihydrocyanostyrene compounds, compositions and methods of use ais nematicides and fungicides.

Nematodes and Fungi are agricultural pests that pose economic difficulties in a variety of crop plants despite the variety of commercially available pesticides. One area of pesticide research is in the pesticidal effectiveness of nitroethane compounds. EP1000934 describes certain nitroethane compounds useful for treating helminth, nematodes, insects or acarid pest or parasites. However, there is a continuing need to develop more effective nematicides. and fungicides.

This object is surprisingly solved by dihydronitrostyrene and dihydrocyanostyrene compounds of formula I:

(I) wherein A, Ar, R, R_1} Y, X, k, / and m are as defined herein: A is hydrogen or X(O)_mR, Ar is phenyl unsubstituted or substituted with any combination of one to five halogen atoms, one or two cyano groups, one or two nitro groups, one to three Cι-C alkyl groups, one to three Cι-C haloalkyl groups, one to three Cι-C alkoxy groups, one to three - haloalkoxy groups, one to three Cι-C alkyl thio groups, one to three C_!-C₄ haloalkyl thio groups, one benzylthio group or one SCH₂C0₂R₂ group, 1- or 2-naphthyl unsubstituted or substituted with any combination of one to five halogen atoms, one or two cyano groups, one or two nitro groups, one to three Q-C₄ alkyl groups, one to three Cι-C haloalkyl groups, one to three Cι-C alkoxy groups, one to three Cj-C₄ haloalkoxy groups, one to three -C₄ alkylthio groups or one to three C]-C₄ haloalkyl thio groups,

piperonyl unsubstituted or substituted with any combination of one to three 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 -Q haloalkoxy groups, one to three C C₄ alkylthio groups or one to three Ci-C₄ haloalkylthio groups,

2-, 3- or 4-pyridyl unsubstituted or substituted with any combination of one to four halogen atoms, one or two cyano groups, one or two nitro groups, one to three -C₄ alkyl groups, one to three -C₄ haloalkyl groups, one to three C C₄ alkoxy groups, one to three Cι-C haloalkoxy groups, one to three C C₄ alkylthio groups or one to three -C₄ haloalkylthio groups,

2- or 3-furyl unsubstituted or substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C₁-C₄ alkyl groups, one to three Cι-C haloalkyl groups, one to three Cι-C alkoxy groups, one to three Ci-C₄ haloalkoxy groups, one to three Cι-C alkylthio groups or one to three C₁-C₄ haloalkylthio groups, or

2- or 3-thienyl unsubstituted or substituted with any combination of one to three 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 -C alkoxy groups, one to three CrC₄ haloalkoxy groups, one to three C₁-C₄ alkylthio groups or one to three C₁-C₄ haloalkylthio groups;

R is hydrogen, C₁-C₄ alkyl, -C₄ alkoxy, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂ -C₄ haloalkenyl, CR₄R₅CO₂R₃, (CH₂)_nNO₂, CR₅R₆CONR₇R₈,

NR₅CO₂R₃, or O(CH₂)_nCO₂R₃;

Ri is hydrogen, C₁-C₄ alkyl, (CH₂)CN, or phenyl unsubstituted or 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 C₁-C₄ haloalkyl groups, one to three -C₄ alkoxy groups, one to three C₁-C₄ haloalkoxy groups, one to three C_Ϊ-C₄ alkylthio groups or one to three C C₄ haloalkylthio groups;

R₂, R₃, R₄, R₅, R₆, R7 and R₈ are each independently hydrogen, C1- ₀ alkyl,

(Ci-Cio haloalkyl), C₂-C_IO alkenyl, C -C₁₀ haloalkenyl,

benzyl unsubstituted or 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 - alkyl groups, one to three Cι-C₄ haloalkyl groups, one to three C C₄ alkoxy groups, one to three -C₄ haloalkoxy groups, one to three C C₄ alkylthio groups or one to three Cι-C₄ haloalkylthio groups, or

phenyl unsubstituted or substituted with any combination of one to five halogen atoms, one or two cyano groups, one or two nitro groups, one to three -C₄ alkyl groups, one to three -d. haloalkyl groups, one to three Cι-C₄ alkoxy groups, one to three C₁-C₄ haloalkoxy groups, one to three C1-C alkylthio groups or one to three - haloalkylthio groups;

k is 1 or 2, provided that if I is 0 then k is 1 and d is double-bonded to C₂

I is 0 or 1, provided that if k is 1 then I is 0 and d is double-bonded to C₂ m is 0, 1 or 2;

n is 0, 1, or 2;

Y is NO₂ or CN; and

X is NRs or S;

or salts, radicals or esters thereof. The invention does not relate to compounds wherein X is S, Y is NO₂ and R is hydrogen, Q-Q. alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, or C₂ -C₄ haloalkenyl or a radical CR₄R₅CO₂R₃ wherein both R₄ and R₅ are H. In another embodiment, the present invention relates to compositions that include a compound of formula (I) and a carrier, provided that when X is S and Y is NO , R is other than hydrogen, C₁-C4 alkyl, Cj-C haloalkyl, C₂-C alkenyl, or C₂ -C haloalkenyl or a radical CR₄R₅CO R₃, wherein both R₄ and R₅ are H.

Furthermore, the invention relates to methods for protecting crops from attack by nematodes by treating the crop with a pesticidally effective amount of the compound of formula (I), provided that when X is S and Y is NO₂, R is other than hydrogen, Q- C₄ alkyl, C C₄ haloalkyl, C₂-C₄ alkenyl, or C_{2 ^}C₄ haloalkenyl or a radical

CR₄R₅CO R₃, wherein both R₄ and R₅ are H. In a further embodiment, the present invention relates to methods for controlling a nematode by treating the nematode with a pesticidally effective amount of the compound of formula (I), provided that when X is S and Y is NO₂, R is other than hydrogen, Q-Q alkyl, Q-Q. haloalkyl, C₂-C alkenyl, or C₂ -C₄ haloalkenyl or a radical CR₄R₅CO R₃, wherein both R₄ and R₅ are H.

Additionally, the present invention relates to methods for controlling fungus by treating the fungus with a pesticidally effective amount of the compound of formula (I).

Before the present compounds, compositions, and methods are disclosed and described, it is to be understood that this invention is not limited to specific synthetic methods of making that may, of course, vary. It is also to be understood that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting. In this specification and in the claims that follow, reference will be made to a number of terms that shall be defined to have the following meanings:

In general, "pesticidally effective amount" means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. One of ordinary skill in the art will recognize that the potency and, therefore, a "pesticidally effective amount" can vary for the various compounds/compositions used in the invention.

By "fungus" is meant any variety of fungus, including, but not limited to, the genus of Ascomycetes, Deuteromycetes, Phycomycetes and Basidiomycetes.

Specifically, they are suitable for controlling the following plant diseases: Alternaria species in vegetables and fruit, Botrytis cinerea (gray mold) in strawberries, vegetables, ornamentals and grapevines, Cercospora arachidicola in groundnuts, Erysiphe cichoracearum and Sphaerotheca fuliginea in cucurbits, Erysiphe graminis (powdery mildew) in cereals, Fusarium and Nerticillium species in a variety of plants,

Helminthosporium species in cereals, Mycosphaerella species in bananas, Phytophthora infestans in potatoes and tomatoes, Plasmopara viticola in grapevines, Podosphaera leucotricha in apples, Pseudocercosporella herpotrichoides in wheat and barley, Pseudocercosporella species in hops and cucumbers, Pseudoperonospora species on cucurbits and hops, Puccinia species in cereals, Pyricularia oryzae in rice, Rhizoctonia - species in cotton, rice and lawn, Septoria nodorum in wheat, Uncinula necator in grapevines, Ustilago species in cereals and sugar cane, Nenturia inaequalis (scab) in apples, and Paecilomyces variotii in the protection of materials (for example wood, paper, paint dispersions, fibers or tissues) and in the protection of stored products. "Locus" means a plant, seed, soil, area, material or environment in which a pest or parasite is growing or may grow. Exemplary plants and seeds include crop plants and their seeds or nuts, such as vines, wheat, barley, apples, tomatoes, rye, soybeans, oats, rice, maize, lawn, bananas, cotton, coffee, sugar cane, grapevines, fruit species, ornamentals, cucumbers, beans, tomatoes, potatoes and cucurbits. As used herein, "nematodes" includes plant parasitic nematodes and nematodes living in the soil. Plant parasitic nematodes include, but are not limited to, ectoparasites such as Xiphinema 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 stem and leaf endoparasites such as Ditylenchus spp., Aphelenchoides spp., and Hirshmaniella spp.

"Salt" as used herein includes salts that can form with, for example, amines, metals, alkaline earth metal bases or quaternary ammonium bases, including zwitterions. Suitable metal and alkaline earth metal hydroxides as salt formers include the salts of barium, aluminum, nickel, copper, manganese, cobalt zinc, iron, silver, lithium, sodium, potassium, magnesium or calcium. Additional salt formers include chloride, sulfate, acetate, carbonate, hydride, and hydroxide. As used throughout, the phrase, "treating a crop" is used to mean that the growing or harvested crop plants and/or soil or water in which the plant is growing has contact with the present compound(s) or composition(s) by application methods known in the art. The phrase "treating fungus" is used to mean that fungus and/or a fungal locus has contact with the present compound(s) or composition(s) by application methods known in the art. Moreover, the phrase "treating a nematode" is used to mean that the nematode and/or the nematode's locus has contact with the present compound(s) or composition(s) by application methods known in the art. As such, the compounds and salts of the present invention can be applied in a number of ways, for example, they can be applied, formulated or unformulated, directly to the fungus and/or - locus or they can be sprayed on, broadcast, dusted on or applied as a cream or paste formulation or they can be applied as slow release granules (i.e. by injecting, shanking, chiseling or working into the soil).

As such, the compounds and salts of the present invention can be applied in a number of ways, for example, they can be applied, formulated or unformulated, directly to the fungus and/or locus or they can be sprayed on, broadcast, dusted on or applied as a cream or paste formulation or they can be applied as slow release granules (i.e. by injecting, shanking, chiseling or working into the soil).

The organic moieties mentioned in the definition of the substituents R, R¹ - R⁸ or as radicals on phenyl, heterocycl or cycloalkyl rings - such as the meaning halogen - are collective terms for individual lists of the separate group members. All carbon chains, i.e. all alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkenyl and haloalkenyl groups can be straight-chain or branched, the prefix C_n-C_m in each case indicating the possible number of carbon atoms in the group. Halogenated substituents preferably carry one, two, three, four or five identical or different halogen atoms, preferably chlorine and/or fluorine atoms. The meaning halogen is in each case fluorine, chlorine, bromine or iodine, preferably fluorine or chlorine.

Cι-C₄-alkyl: methyl, ethyl, n-propyl, CH(CH₃)₂, n-butyl, CH(CH₃)-C₂H₅, CH₂- CH(CH₃)₂ and C(CH₃)₃;

C₁-C₄-alkoxy: methoxy, ethoxy, n-propoxy, OCH(CH₃)₂, n-butoxy, OCH(CH₃)- C₂H₅, OCH₂-CH(CH₃)₂ and OC(CH₃)₃;

C₁-C₄-haloalkyl: a C₁-C₄-alkyl radical as mentioned above, which is partially or completely substituted, preferably by one to five halogen atoms, e.g. by fluorine, chlorine, bromine and/or iodine, i.e., for example, CH₂F, CHF₂, CF₃, CH₂C1, dichloromethyl, trichloromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2- difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, C₂Fs, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3- dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3- trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, l-(fluoromethyl)-2- fluoroethyl, l-(chloromethyl)-2-chloroethyl, l-(bromomethyl)-2-bromoethyl, 4- fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl, especially CH₂F, CHF₂, CF₃, CH₂C1, dichloromethyl, trichloromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, and 2,2,2-trifluoroethyl;

Cι-Cιo-alkyl: an alkyl radical having from 1 to 10, preferably from 1 to 8, especially from 1 to 6 carbon atoms, such as Q-Q-alkyl as mentioned above, and also, for example, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2- dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1- methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1 -dimethylbutyl, 1,2- dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3- dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1 -ethyl- 1-methylpropyl or l-ethyl-2-methylpropyl, preferably methyl, ethyl, n-propyl, 1 -methylethyl , n-butyl , 1,1 -dimethylethyl , n-pentyl or n-hexyl ;

Q-Cio-haloalkyl: a Q-Cio-alkyl radical as mentioned above which is partially or fully substituted, preferably by one to five halogen atoms, e.g. by fluorine, chlorine, bromine and/or iodine, i.e. for example one of the radicals mentioned under Q-C₄- haloalkyl, and also 5-fluoro-l-pentyl, 5-chloro-l-pentyl, 5-bromo-l-pentyl, 5-iodo-l- pentyl, 5,5,5-trichloro-l-pentyl, undecafluoro- pentyl, 6-fluoro-l-hexyl, 6-chloro-l- hexyl, 6-bromo-l-hexyl, 6-iodo-l-hexyl, 6,6,6-trichloro-l-hexyl or dodecafluorohexyl; CrQ-alkylthio: e.g. methylthio, ethylthio, n-propylthio, isopropylthio, 2- butylthio, n-butylthio, isobutylthio or tert.-butylthio;

C₁-C₄-haloalkylthio: a CrQ-alkylthio radical as mentioned above, which is partially or completely substituted, preferably by one to five halogen atoms, e.g. by fluorine, chlorine, bromine and/or iodine, i.e., for example, SCH₂F, SCHF₂, SCF , SCH₂C1, dichloromethylthio, trichloromethylthio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 2-fluoroethylthio, 2- chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2,2,2- trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2- dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio, C₂F₅, 2-fluoropropylthio, 3- fluoropropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio, 2-chloropropylthio, 3- chloropropylthio, 2,3-dichloropropylthio, 2-bromopropylthio, 3-bromopropylthio, 3 ,3 ,3-trifluoropropylthio, 3 ,3 ,3-trichloropropylthio, 2,2,3 ,3 ,3-pentafluoropropylthio, heptafluoropropylthio, l-(fluoromethyl)-2-fluoroethylthio, l-(chloromethyl)-2- chloroethylthio, l-(bromomethyl)-2-bromoethylthio, 4-fluorobutylthio, 4- chlorobutylthio, 4-bromobutylthio or nonafluorobutylthio; Ci-G_t-haloalkoxy: a Cι-C₄-alkoxy radical as mentioned above, which is partially or completely substituted, preferably by one to five halogen atoms, e.g. by fluorine, chlorine, bromine and/or iodine, i.e., for example OCH₂F, OCHF₂, OCF₃, OCH₂Cl, OCH(Cl)₂, OCCl₃, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2- difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC₂F₅, 2- fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2- chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3- bromopropoxy, 3,3,3-trifluoroρropoxy, 3,3,3-trichloropropoxy, OCH₂-C₂F₅, OCF₂- C₂F₅, l-(CH₂F)-2-fluoroethoxy, l-(CH₂Cl)-2-chloroethoxy, l-(CH₂Br)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy, preferably OCHF₂, OCF₃, dichlorofluoromethoxy, chlorodifluoromethoxy or 2,2,2- trifluoroethoxy; CrQo-haloaloxy: a Q-Qo-alkoxy radical as mentioned above which is partially or fully substituted, preferably by one to five halogen atoms, e.g. by fluorine, chlorine, bromine and/or iodine, i.e. for example one of the radicals mentioned under C₁-C₄-haloalkoxy, and also 5-fluoro-l -pentyloxy, 5 -chloro-1 -pentyloxy, 5-bromo-l- pentyloxy, 5-iodo-l-pentyloxy, 5,5,5-trichloro-l-pentyloxy, undecafluoro- pentyloxy, 6-fluoro-l-hexyloxy, 6-chloro-l-hexyloxy, 6-bromo-l-hexyloxy, 6-iodo-l-hexyloxy, 6,6,6-trichloro-l-hexyloxy or dodecafluorohexyloxy;

C₂-C_!o-alkenyl: alkenyl, having from 2 to 10, preferably from 2 to 6 and especially from 2 to 4 carbon atoms, e.g. ethenyl, prop-1-en-l-yl, allyl, 1- methylethenyl, 1-buten-l-yl, l-buten-2-yl, l-buten-3-yl, 2-buten-l-yl, 1-methylprop-l- en-l-yl, 2-methylprop-l-en-l-yl, l-methyl-prop-2-en-l-yl, 2-methyl-prop-2-en-l-yl, n- penten-1-yl, n-penten-2-yl, n-penten-3-yl, n-penten-4-yl, 1-methyl-but-l-en-l-yl, 2- methylbut-1-en-l-yl, 3-methylbut-l-en-l-yl, l-methylbut-2-en-l-yl, 2-methylbut-2-en- 1-yl, 3-methylbut-2-en-l-yl, l-methylbut-3-en-l-yl, 2-methylbut-3-en-l-yl, 3- methylbut-3-en-l-yl, l,l-dimethylprop-2-en-l-yl, 1,2-dimethylprop-l-en-l-yl, 1,2- dimethylprop-2-en-l-yl, l-ethylprop-l-en-2-yl, l-ethylprop-2-en-l-yl, n-hex-1-en-l-yl, n-hex-2-en-l-yl, n-hex-3-en-l-yl, n-hex-4-en-l-yl, n-hex-5-en-l-yl, 1-methylpent-l-en- 1-yl, 2-methylpent-l-en-l-yl, 3-methylpent-l-en-l-yl, 4-methylpent-l-en-l-yl, 1- methylpent-2-en-l-yl, 2-methylpent-2-en-l-yl, 3-methyl-pent-2-en-l-yl, 4-methylpent- 2-en-l-yl, l-methylpent-3-en-l-yl, 2-methylpent-3-en-l-yl, 3-methylpent-3-en-l-yl, 4- methylpent-3-en-l-yl, l-methylpent-4-en-l-yl, 2-methyl-pent-4-en-l-yl, 3-methylpent- 4-en-l-yl, 4-methylpent-4-en-l-yl, l,l-dimethylbut-2-en-l-yl, l,l-dimethylbut-3-en-l- yl, 1,2-dimethylbut-l-en-l-yl, l,2-dimethylbut-2-en-l-yl, l,2-dimethylbut-3-en-l-yl, 1,3-dimethylbut-l-en-l-yl, l,3-dimethylbut-2-en-l-yl, l,3-dimethylbut-3-en-l-yl, 2,2-dimethylbut-3-en-l-yl, 2,3-dimethylbut-l-en-l-yl, 2,3-dimethylbut-2-en-l-yl, 2,3-dimethylbut-3-en-l-yl, 3,3-dimethylbut-l-en-l-yl, 3,3-dimethylbut-2-en-l-yl, 1-ethylbut-l-en-l-yl, l-ethylbut-2-en-l-yl, l-ethyl-but-3-en- 1-yl, 2-ethylbut-l-en-l-yl, 2-ethylbut-2-en-l-yl, 2-ethylbut-3-en-l-yl, 1,1,2- trimethylprop-2-en- 1 -yl , 1 -ethyl- 1 -methylprop-2-en- 1 -yl , 1 -ethyl-2-methylprop- 1 -en- 1 - yl or l-ethyl-2-methylprop-2-en-l-yl;

C₂-C₁₀-haloalkenyl: C₂-C₁₀-alkenyl as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e. for example 2- chloroethenyl, 2-chloroallyl, 3-chloroallyl, 2,3-dichloroallyl, 3,3-dichloroallyl, 2,3,3- trichloroallyl, 2,3-dichlorobut-2-enyl, 2-bromoallyl, 3-bromoallyl, 2,3-dibromoallyl, 3,3-dibromoallyl, 2,3,3-tribromoallyl and 2,3-dibromobut-2-enyl.

In preferred compounds of the formula I the variables A, Ar, R, R^ X, k, and m alone or in combination have the following meanings: A is hydrogen; Rj is hydrogen; k is 2 and 1 is 1;

X(O)_m is S or NR_5a , wherein R_5a is as defined for R⁵ and preferably hydrogen or

Q-Q-alkyl; Ar is phenyl which is unsubstituted or substituted as defined above, piperonyl, which is unsubstituted or substituted as defined above, or 2- or 3-thienyl, which is unsubstituted or carries one halogen atom.

More preferably Ar is phenyl which is unsubstituted or which carries one substituent in the 4-position, or two substituents in the 3- and 4-positon or in the 3 and 5-postion. Preferred substituents on phenyl are alkyl, especially methyl, alkoxy, especially methoxy and halogen, especially fluoro, chloro and bromo.

More preferably is also unsubstituted piperonyl (= benzo[l,3]dioxolyl), preferably benzo [ 1 ,3] dioxol-5-yl.

R is preferably selected from C₁-C₄-alkoxy, CH₂CN, CH₂CH₂NO₂, CR_4aR₅CO₂R₃, wherein R_4a has-the meanings given for R⁴ but is different from H, CR₅R₆CONR₇R₈, NR₅CO₂R₃, or O(CH₂)„CO₂R₃ with n being 1 or 2. Herein the variables R³, R , R⁵, R⁶ are preferably as follows: R³ H, C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C -haloalkenyl, C₁-C₄-haloalkyl, phenyl or benzyl, more preferably H or d-Q-alkyl; R^4a Ci-0₄-alkyl, more preferably methyl;

R⁵ H, d-C₄-alkyl, more preferably H or methyl; R⁶ H, d-C₄-alkyl, more preferably H or methyl; R⁷ H, Cι-C₄-alkyl, more preferably methyl or ethyl; R⁸ C i -d-alkyl , more preferably methyl or ethyl . In a preferred embodiment of the invention the variables X(O)_m and R together form a group NR_5a-C₁-C₄-alkoxy, SCH₂CN, SCH₂CH₂NO₂, SCR _aR₅CO₂R₃, wherein R _a has the meanings given for R⁴ but is different from H, SCR₅R₆CONR₇R₈, NR_5aNR_5bCO₂R₃, or NR_5aO(CH₂)_nCO₂R₃ with n being 1 or 2. Herein the variables R³, R⁴ , R⁵, R^5a, R⁶, R⁷ and R⁸ are defined as above and more preferably as follows: R³ H, d-C -alkyl, C₂-C -alkenyl, C₂-C -haloalkenyl, C₁-C₄-haloalkyl, phenyl or benzyl, more preferably H or d-Q-alkyl; R^4a Cι-C₄-alkyl, more preferably methyl;

R⁵ H, d-d-alkyl, more preferably H or methyl; R^5a H, d-C₄-alkyl, more preferably H; R⁶ H, C i -C₄-alkyl , more preferably H or methyl ; R⁷ H, d-C₄-alkyl, more preferably methyl or ethyl; R⁸ CrC₄-alkyl, more preferably methyl or ethyl.

R^5b is as defined for R⁵, preferably H or C₁-C₄-alkyl, more preferably H. With respect to their fungicidal and nematodicidal activity compounds of formula I are preferred wherein Y is NO₂.

When X is S and Y is NO₂, R is preferably also different from CH₂C(O)NR₇R₈. Desirable compounds of formula I include the following: 2-[l-(4-Methoxy- phenyl)-2-nitro-ethylsulfanyl]-propionic acid; 2-(2-Nitro-l -phenyl-ethylsulf anyl)- propionic acid; 2-(l-Benzo[l,3]dioxol-5-yl-2-nitro-ethylsulfanyl)-propionic acid; 2-(2- Nitro- 1 -p-tolyl-ethylsulf anyl)-propionic acid; 2-(2-Nitro- 1 -phenyl-ethylsulf anyl)- propionic acid ethyl ester; 2-[l-(4-Methoxy-phenyl)-2-nitro-ethylsulfanyl]-propionic acid ethyl ester; 2-(l-Benzo[l,3]dioxol-5-yl-2-nitro-ethylsulfanyl)-propionic acid ethyl ester; 2-(2-Nitro-l -p-tolyl-ethylsulf anyl)-propionic acid ethyl ester; (2-Nitro-l-phenyl- ethylsulfanyl)-acetonitrile; (l-Benzo[l,3]dioxol-5-yl-2-nitro-ethylsulfanyl)-acetonitrile; (2-Nitro- 1-p-tolyl-ethylsulf anyl)-acetonitrile; 2-Methyl-2-(2-nitro- 1 -phenyl- ethylsulf anyl)-propionic acid; 2- [ 1 -(4-Methoxy-phenyl)-2-nitro-ethylsulf anyl]-2- methyl-propionic acid; 2-(l-Benzo[l,3]dioxol-5-yl-2-nitro-ethylsulfanyl)-2-methyl- propionic acid; 2-Methyl-2-(2-nitro-l -p-tolyl-ethylsulf anyl)-propionic acid; 2-[l-(4- Fluoro-phenyl)-2-nitro-ethylsulfanyl]-propionic acid; 2-[l-(4-Fluoro-phenyl)-2-nitro- ethylsulfanylj-propionic acid ethyl ester; 2-[l-(4-Fluoro-phenyl)-2-nitro-ethylsulfanyl]- 2-methyl-propionic acid; N,N-Dimethyl-2-(2-nitro-l-ρhenyl-ethylsulfanyl)-acetamide; 2-[l-(4-Methoxy-phenyl)-2-nitro-ethylsulfanyl]-N,N-dimethyl-acetamide; 2-(l-

Benzo[l,3]dioxol-5-yl-2-nitro-ethylsulfanyl)-N,N-dimethyl-acetamide; N,N-Dimethyl- 2-(2-nitro-l-p-tolyl-ethylsulfanyl)-acetamide; 2-[l-(4-Fluoro-phenyl)-2-nitro- ethylsulf anyl] -N,N-dimethyl-acetamide; N,N-Diethyl-2-(2-nitro- 1 -phenyl- ethylsulfanyl)-acetamide; N,N-Diethyl-2-[l-(4-methoxy-phenyl)-2-nitro-ethylsulfanyl]- acetamide; 2-(l-Benzo[l,3]dioxol-5-yl-2-nitro-ethylsulfanyl)-N,N-diethyl-acetamide; N,N-Diethyl-2-(2-nitro- 1 -p-tolyl-ethylsulf anyl)-acetamide; N,N-Diethyl-2-[ 1 -(4-fluoro- phenyl)-2-nitro-ethylsulf anyl] -acetamide; [2-Nitro- 1 -(2-nitro-ethylsulf anyl)-ethyl] - benzene; l-Methoxy-4-[2-nitro-l-(2-nitro-ethylsulfanyl)-ethyl]-benzene; 5-[2-Nitro-l- (2-nitro-ethylsulfanyl)-ethylj-benzo[l,3]dioxole; l-Methyl-4-[2-nitro-l-(2-nitro- ethylsulfanyl)-ethyl]-benzene; l-Fluoro-4-[2-nitro-l-(2-nitro-ethylsulfanyl)~ethyl]- benzene; O-Ethyl-N-(2-nitro-l-phenyl-ethyl)-hydroxylamine; O-Ethyl-N-[l-(4- methoxy-phenyl)-2-nitro-ethyl]-hydroxylamine; N-(l-Benzo[l,3]dioxol-5-yl-2-nitro- ethyl)-O-ethyl-hydroxylamine; O-Ethyl-N-(2-nitro-l-p-tolyl-ethyl)-hydroxylamine; O- Ethyl-N-[l-(4-fluoro-phenyl)-2-nitro-ethyl]-hydroxylamine; [N-(2-Nitro-l-phenyl- ethyl)aminooxy] -acetic acid; {N-[l-(4-Methoxy-phenyl)-2-nitro-ethyl]aminooxy}- acetic acid; [N-(l-Benzo[l,3]dioxol-5-yl-2-nitro-ethyl)aminooxy]-acetic acid; [N-(2- Nitro- 1 -p-tolyl-ethyl)aminooxy] -acetic acid; { N-[ l-(4-Fluoro-phenyl)-2-nitro- ethyl] aminooxy} -acetic acid; [l-(4-Chloro-phenyl)-2-cyano-ethylsulfanyl]-acetic acid methyl ester; [N-(2-Nitro-l-phenyl-ethyl)aminooxy]-acetic acid methyl ester; {N-[l-(4- Methoxy-phenyl)-2-nitro-ethyl] aminooxy} -acetic acid methyl ester; [N-(l- Benzo[l,3]dioxol-5-yl-2-nitro-ethyl)aminooxy]-acetic acid methyl ester; [N-(2-Nitro-l- p-tolyl-ethyl)aminooxy]-acetic acid methyl ester; {N-[l-(4-Fluoro-phenyl)-2-nitro- ethyl]aminooxy}-acetic acid methyl ester; [2-Cyano-l-(4-methoxy-phenyl)- ethylsulf anyl] -acetic acid methyl ester; [2-Cyano-l-(3,4-dimethoxy-phenyl)- ethylsulf anyl] -acetic acid methyl ester; (2-Cyano-l -phenyl-ethylsulf anyl)-acetic acid methyl ester; N'-(2-Nitro-l-phenyl-ethyl)-hydrazinecarboxylic acid ethyl ester; N'-[l- (4-Fluoro-phenyl)-2-nitro-ethyl]-hydrazinecarboxylic acid ethyl ester; N'-(2-Nitro-l-p- tolyl-ethyl)-hydrazinecarboxylic acid ethyl ester; N'-(l-Benzo[l,3]dioxol-5-yl-2-nitro- ethyl)-hydrazinecarboxylic acid ethyl ester; N'-[l-(4-Methoxy-phenyl)-2-nitro-ethyl]- hydrazinecarboxylic acid ethyl ester; 2-[l-(4-Bromo-thiophen-2-yl)-2-nitro- ethylsulfanyl]-propionic acid; {N-[l-(4-Bromo-thiophen-2-yl)-2-nitro- ethyl] aminooxy} -acetic acid; 2-[l-(4-Bromo-thiophen-2-yl)-2-nitro-ethylsulfanyl]- N,N-diethyl-acetamide; 4-Bromo-2- [2-nitro- 1 -(2-nitro-ethylsulf anyl)-ethyl] -thiophene; 2-[l-(4-Bromo-thiophen-2-yl)-2-nitro-ethylsulfanyl]-propionic acid; and 4-Bromo-2- [2-nitro-l-(2-nitro-ethylsulfanyl)-ethyl]-thiophene. With respect to their fungicidal activity compounds of the formula I are especially preferred, wherein the variables A, Ar, R, Ri, X, k, I and m alone or in combination have the following meanings: A is hydrogen; R] is hydrogen; k is 2 and 1 is 1;

Ar is phenyl which is unsubstituted or substituted as defined above, piperonyl, which is unsubstituted or substituted as defined above, or 2- or 3-thienyl, which is unsubstituted or carries one halogen atom. More preferably Ar is phenyl which is unsubstituted or which carries one substituent in the 4-position, or two substituents in the 3- and 4-positon or in the 3 and 5-postion. Preferred substituents on phenyl are alkyl, especially methyl, alkoxy, especially methoxy and halogen, especially fluoro, chloro and bromo. More preferably is also unsubstituted piperonyl (= benzo[l,3]dioxolyl), preferably benzo[l,3]dioxol-5-yl;and the variables

X(O)_m and R together form a group NR_5a-C₁-C₄-alkoxy, SCH₂CN, SCH₂CH₂NO₂,

SCR_4aR₅CO₂R₃, wherein R_4a has the meanings given for R⁴ but is different from H, SCR₅R₆CONR₇R₈, NR_5aNR_5bCO₂R₃, or NR_5aO(CH₂)_nCO₂R₃ with n being 1 or 2. Herein the variables R³, R^4a, R⁵, R^5a, R⁶, R⁷ and R⁸ are defined as above. Most preferred are compounds I, wherein X(O)_m and R together form a group

NR_5a-CrC₄-alkoxy, SCHR_4aCO₂R3, wherein R_4a has the meanings given for R⁴ but is different from H and preferably mehtyl, or NR_5aO(CH₂)_nCO₂R₃. More desirable compounds for use as fungicides are: 2-(2-Nitro-l-phenyl- ethylsulfanyl)-propionic acid; (l-Benzo[l ,3]dioxol-5-yl-2-nitro-ethylsulfanyl)- acetonitrile; 2-Methyl-2-(2-nitro-l-phenyl-ethylsulfanyl)-propionic acid; 2-Methyl-2- (2-nitro-l -p-tolyl-ethylsulf anyl)-propionic acid; 2-[l-(4-Fluoro-phenyl)-2-nitro- ethylsulfanyl]-propionic acid; 2-[l-(4-Fluoro-phenyl)-2-nitro-ethylsulfanyl]-propionic acid ethyl ester; 2-[l-(4-Fluoro-phenyl)-2-nitro-ethylsulfanyl]-2-methyl-propionic acid; N,N-Diethyl-2-(2-nitro-l-p-tolyl-ethylsulfanyl)-acetamide; l-Methyl-4-[2-nitro- l-(2-nitro-ethylsulfanyl)-ethyl]-benzene; l-Fluoro-4-[2-nitro-l-(2-nitro-ethylsulfanyl)- ethyl] -benzene; O-Ethyl-N-[l-(4-methoxy-phenyl)-2-nitro-ethyl]-hydroxylamine; O- Ethyl-N-(2-nitro-l-p-tolyl-ethyl)-hydroxylamine; O-Ethyl-N-[l-(4-fluoro-phenyl)-2- nitro-ethyl]-hydroxylamine [N-(2-Nitro-l-p-tolyl-ethyl)aminooxy]-acetic acid; {N-[l- (4-Fluoro-phenyl)-2-nitro-ethyl] aminooxy} -acetic acid; [N-(2-Nitro- 1 -phenyl- ethyl)aminooxy] -acetic acid methyl ester; {N-[l-(4-Methoxy-phenyl)-2-nitro- ethyl] aminooxy} -acetic acid methyl ester; [N-(l-Benzo[l,3]dioxol-5-yl-2-nitro- ethyl)aminooxy] -acetic acid methyl ester; [N-(2-Nitro-l-p-tolyl-ethyl)aminooxy]- acetic acid methyl ester; {N-[l-(4-Fluoro-phenyl)-2-nitro-ethyl]aminooxy}-acetic acid methyl ester; 2-[l-(4-Bromo-thiophen-2-yl)-2-nitro-ethylsulfanyl]-propionic acid; and {N-[l-(4-BiOmo-thiophen-2-yl)-2-nitro-ethyl]aminooxy}-acetic acid.

Even more desirable compounds for use as fungicides are: 2-(2-Nitro-l-phenyl- ethylsulfanyl)-propionic acid; (l-Benzo[l,3]dioxol-5-yl-2-nitro-ethylsulfanyl)- acetonitrile; N,N-Diethyl-2-(2-nitro-l-p-tolyl-ethylsulfanyl)-acetamide; [N-(2-Nitro- l-p-tolyl-ethyl)aminooxy] -acetic acid methyl ester; {N-[l-(4-Fluoro-phenyl)-2-nitro- ethyl] aminooxy} -acetic acid methyl ester; and 2-[l-(4-Bromo-thioplιen-2-yl)-2-nitro- ethylsulfanyl]-propionic acid.

With respect to their nematicidal activity compounds of the formula I are especially preferred, wherein the variables A, Ar, R, R_ls X, k, / and m alone or in combination have the following meanings: A is hydrogen; Ri is hydrogen; k is 2 and 1 is 1; Ar is phenyl which is unsubstituted or substituted as defined above, or piperonyl, which is unsubstituted or substituted as defined above.

More preferably Ar is phenyl which is unsubstituted or which carries one substituent in the 4-position, or two substituents in the 3- and 4-positon or in the

3 and 5-postion. Preferred substituents on phenyl are alkyl, especially methyl, alkoxy, especially methoxy and halogen, especially fluoro, chloro and bromo.

More preferably is also unsubstituted piperonyl (= benzo[l,3]dioxolyl), preferably benzo[l,3]dioxol-5-yl;and the variables X(O)_m and R together form a group NR_5a-C₁-C₄-alkoxy, SCH₂CN, SCH₂CH₂NO₂,

SCR_4aR₅CO₂R₃, wherein R_4a has the meanings given for R⁴ but is different from H, SCR₅R₆CONR₇R₈, or NR_5aO(CH₂)_nCO₂R₃ with n being 1 or 2. Herein the variables R³, R^4a, R⁵, R^5a, R⁶, R⁷ and R⁸ are defined as above. Most preferred are compounds I, wherein X(O)_m and R together form a group NR_5a-C₁-C₄- alkoxy, SCHR_4aCO₂R₃, wherein R _a has the meanings given for R⁴ but is different from H and preferably mehtyl, or NR_5aO(CH₂)_nCO₂R₃. More desirable compounds for use as nematicides are: 2-(2~Nitro-l -phenyl - ethylsulfanyl)-propionic acid; 2-(l-Benzo[l,3]dioxol-5-yl-2-nitro-ethylsulfanyl)- propionic acid; 2- (2-Nitro- 1 -p-tolyl-ethylsulf anyl)-propionic acid; 2-(2-Nitro-l- phenyl-ethylsulfanyl)-propionic acid ethyl ester; 2-[l-(4-Methoxy-phenyl)-2-nitro- ethylsulf anyl] -propionic acid ethyl ester; 2-(l-Benzo[l,3]dioxol-5-yl-2-nitro- ethylsulfanyl)-propionic acid ethyl ester; 2-(2-Nitro-l -p-tolyl-ethylsulf anyl)-propionic acid ethyl ester; (l-Benzo[l,3]dioxol-5-yl-2-nitro-ethylsulfanyl)-acetonitrile; (2-Nitro- l-p-tolyl-ethylsulfanyl)-acetonitrile; 2-[l-(4-Methoxy-phenyl)-2-nitro-ethylsulfanyl]- N,N-dimethyl-acetamide; 2-(l-Benzo[l,3]dioxol-5-yl-2-nitro-ethylsulfanyl)-N,N- dimethyl-acetamide; N,N-Dimethyl-2-(2-nitro-l-p-tolyϊ-ethylsulfanyl)-acetamide; N,N-Diethyl-2-(2-nitro- 1 -phenyl-ethylsulf anyl)-acetamide; N,N-Diethyl-2- [ 1 -(4- methoxy-phenyl)-2-nitro-ethylsulfanyl]-acetamide; N,N-Diethyl-2-(2-nitro-l-p-tolyl- ethylsulfanyl)-acetamid; [2-Nitro-l-(2-nitro-ethylsulfanyl)-ethyl]-benzene; 1-

Methoxy-4- [2-nitro- 1 -(2-nitro-ethylsulf anyl)-ethyl] -benzene ; 5- [2-Nitro- 1 -(2-nitro- ethylsulfanyl)-ethyl]-benzo[l,3]dioxole; {N-[l-(4-Methoxy-phenyl)-2-nitro- ethyl] aminooxy} -acetic acid; [N-(l-Benzo[l,3]dioxol-5-yl-2-nitro-ethyl)aminooxy]- acetic acid; {N-[l-(4-Fluoro-phenyl)-2-nitro-ethyl]aminooxy}-acetic acid; [N-(l- Benzo[l,3]dioxol-5-yl-2-nitro-ethyl)aminoox-y]-acetic acid methyl ester; 2-[l-(4- Bromo-thiophen-2-yl)-2-nitro-ethylsulfanyl]-propionic acid; and 2-[l-(4-Bromo- thiophen-2-yl)-2-nitro-ethylsulfanyl]-N,N-diethyl-acetamide.

Even more desirable compounds for use as nematicides are: 2-(2-Nitro-l- phenyl-ethylsulfanyl)-propionic acid; 2-[l-(4-Methoxy-phenyl)-2-nitro-ethylsulfanyl]- N,N-dimethyl-acetamide; N,N-Dimethyl-2-(2-nitro- 1 -p-tolyl-ethylsulf anyl)-acetamide; N,N-Diethyl-2-(2-nitro-l-p-tolyl-ethylsulfanyl)-acetamide; [2-Nitro-l-(2-nitro- ethylsulfanyl)-ethyl]-benzene; l-Methoxy-4-[2-nitro-l-(2-nitro-ethylsulfanyl)-ethyl]- benzene; 5-[2-Nitro-l-(2-nitro-ethylsulfanyl)-ethyl]-benzo[l,3]dioxole; and [N-(l- Benzo[l,3]dioxol-5-yl-2-nitro-ethyl)aminooxy]-acetic acid. The compounds of formula I may be used to prevent attack on crops by nematodes by treating the crop with a pesticidally effective amount of a compound of formula (I). Moreover, nematodes and or fungus may be controlled by applying a pesticidally effective amount of the compound of formula (I) to the target parasite/pest or its locus. As such, the application may be carried out before or after the infection of the locus, growing crops, or harvested crops by fungi or nematodes.

A pesticidally effective amount of the composition will vary according to the prevailing conditions such as desired fungicidal effect and duration, weather, target species, locus, mode of application, and the like. In general, for use in treating crop plants, the rate of application of the compound and/or composition of this invention may be in the range of about 0.1 g to about 4000 g per hectare, desirably from about 25 g to about 600 g per hectare as the active ingredient, more desirably from about 50 g to about 500 g per hectare. For use in treating seeds, the typical rate of application is of from about 1 g to about 500 g per kilogram of seeds, desirably from about 2 g to about 300 g per kilogram of seeds, more desirably from about 10 g to about 200 g per kilogram of seeds. Customary application rates in the protection of materials are, for example, from about 0.001 g to about 2 kg, desirably from about 0.005 g to about 1 kg, of active compound per cubic meter of treated material. The present compounds may be applied formulated or unformulated. Typical formulations contain the active ingredient in a range from about 0.1 ppm to about 10,000 ppm and may also contain a carrier. The carrier may be any agronomically or pharmaceutically acceptable carrier, including natural and synthetic organic and inorganic ingredients that facilitate dispersion of the composition or compound and contact with the pesticidal target. The carrier may be solid (e.g. clays, synthetic . silicates, silica, resins, waxes, kaolin, bentonite, dolomite, calcium carbonate, talc, powdered magnesia, Fuller's earth, gypsum, diatomaceous earth, China clay, and combinations thereof); liquid (e.g. water, aqueous solutions, N-methylpyrrolidone, kerosene, cyclohexanone, methylethyl ketone, acetonitrile, methanol, ethanol, isopropyl alcohol, acetone, butyl cellosolved, 2-ethyl-lhexanol, cyclohexanone, methyl cellulose, polyvinyl alcohol, sodium lignin sulfonates, polymeric alkyl naphthalene sulfonates, sodium naphthalene sulfonate, polymethylene bisnaphthalenesulfonate, sodium N- methyl-N-(long chain acid) laureates, hydrocarbons and other water-immiscible ethers, esters and ketones, and combinations thereof); or a combination of solid and liquid carriers.

The compositions of the present invention may also contain one or more surfactants to increase the biological effectiveness of the active ingredient. Suitable surface active ingredients include surfactants, emulsifying agents, and wetting agents. A wide range of surfactants is available and can be selected readily by those skilled in the art from "The Handbook of Industrial Surfactants," 2nd Edition, Gower (1997), which is incorporated herein by reference in its entirety for all purposes. There is no restriction on the type or chemical class of surfactant that can be used. Nonionic, anionic, cationic and amphoteric types, or combinations of more than one of these types, are all useful in particular situations.

Among nonionic surfactants, exemplary classes include polyoxyethylene alkyl, alkyne, alkynyl or alkylaryl ethers, such as polyoxyethylene primary or secondary alcohols, alkylphenols or acetylenic diols; polyoxyethylene alkyl or alkyne esters, such as ethoxylated fatty acids; sorbitan alkylesters, whether ethoxylated or not; glyceryl alkylesters; sucrose esters; and alkyl polyglycosides. Exemplary anionic surfactant classes include fatty acids, sulfates, sulfonates, and phosphate mono- and diesters of alcohols, alkylphenols, polyoxyethylene alcohols and polyoxyethylene alkylphenols, and carboxylates of polyoxyethylene alcohols and polyoxyethylene alkylphenols. These can be used in their acid form but are more typically used as salts, for example sodium, potassium or ammonium salts.

Cationic surfactants classes include polyoxyethylene tertiary alkylamines or alkenylamines, such as ethoxylated fatty amines, quaternary ammonium surfactants and polyoxyethylene alkyletheramines. Representative specific examples of such cationic - - surfactants include polyoxyethylene (5) cocoamine, polyoxyethylene (1.5) tallowamine, distearyldimethylammonium chloride, N-dodecylpyridine chloride and polyoxypropylene (8) ethoxytrimethylammonium chloride. Many cationic quaternary ammonium surfactants of diverse structures are known in the art to be useful in combination with active ingredients and can be used in compositions contemplated herein.

Suitable emulsifying agents and wetting agents include, but are not limited to, ionic and nonionic types such as polyacrylic acid salts, lignosulphonic acid salts, phenolsulphonic or naphthalenesulphonic acids, products of polycondensation of ethylene oxide with fatty alcohols, fatty acids or fatty amines, substituted phenols (especially alkylphenols or arylphenols), sulphonosuccinic acid ester salts, taurine derivatives (especially alkyl taurates), phosphoric esters of alcohols or products of polycondensation of ethylene oxide with phenols, esters of fatty acids with polyhydric alcohols, and derivatives having sulphate, sulphonate and phosphate groups, of the compounds above.

Compositions of this invention may also contain other active ingredients, for example other fungicides; insecticides, fertilizers such as ammonium nitrate, urea, potash, and super phosphate; phytotoxicants and plant growth regulators; safeners; and pesticides. These additional ingredients may be used sequentially or in combination with the above-described compositions. For example, the plant(s) may be sprayed with a composition of this invention either before or after being treated with other active ingredients. Such sequential applications may be performed by applying the combination of active ingredients individually within a one day period or less, such as separate applications of the individual pesticides within less than 1 hour, less than 5 hours, less than 10 hours, less than 14 hours, or less than 17 hours.

Other optional components may be admixed with the present compositions to facilitate the application and/or effectiveness of the active ingredient. To this end, optional components that may be added include antifoaming agents including silicone based antifoaming agents; thickening agents such as fumed silica; antimicrobial agents; antioxidants; buffers; dyes; perfumes; stabilizing agents; and antifreezing agents. Exemplary antifreezing agents include but are not limited to, glycols such as propylene glycol and ethylene glycol, N-methylpyrrolidone, cyclohexanone, and alcohols such as ethanol and methanol.

Compositions of the present invention may be present in any effective formulation, including, but not limited to, a dusting powder or granule; dispersible powder, granule or grain; aqueous dispersion; suspension; paste; or emulsion. As such, the composition may be applied by any effective method including, but not limited to, spraying, atomizing, dusting, spreading or pouring.

Powders, including dusting powders or granules and dispersible powders, granules or grains contain at least one active ingredient and an inert solid extender or carrier, such as kaolin, bentonite, dolomite, calcium carbonate, talc, powdered magnesia, Fuller's earth, gypsum, diatomaceous earth and China clay. Dispersible powders, granules and grains typically also include one or more wetting and dispersing agents, such as surfactants.

The composition of this invention may be made up as granules comprising 0.5 to 40%, preferably 2 to 30% by weight of the active compound of this invention as active ingredient; 1 to 20%, preferably 2 to 10% by weight of the surfactant; and 40 to 98.5%, preferably 20 to 96% by weight of solid carrier. Formulated into a dust, the composition may include 0.5 to 40%, preferably 1 to 35% by weight of the active ingredient; and 99.5 to 60%, preferably 99 to 65% by weight of finely divided solid carrier.

The composition of this invention may also be formulated into a paste comprising 0.1 to 20%, preferably 1 to 10% by weight of the active ingredient, 1 to 20%, preferably 2 to 10% by weight of surfactant; and 60 to 98.9%, preferably 80 to 97% by weight of paste base. In a wettable powder formulation, the composition typically includes 5 to 95%, preferably 10 to 50% by weight of the new compounds of this invention as active ingredient; 1 to 20%, preferably 5 to 10% by weight of surfactant; and 4 to 44%, preferably 40 to 85% by weight of solid carrier, the solid carrier being preferably ammonium sulfate.

The aqueous dispersions or emulsions may be prepared by dissolving the active ingredient in an organic solvent optionally containing wetting, dispersing or emulsifying agent(s) and then adding the mixture to water which may also contain wetting, dispersing or emulsifying agents(s). Suitable organic solvents are kerosene, cyclohexanone, methylethyl ketone, acetone, methanol, acetonitrile, and the like. The compositions may also be in the form of liquid preparations for use as dips or sprays which are -generally aqueous dispersions or emulsions containing the active ingredient in the presence of one or more of wetting agent(s), dispersing agent(s), emulsifying agent(s) or suspending agent(s).

Typical liquid solutions include the active ingredient, a carrier, and optionally, a surface active agent. The dilute solutions of the present compositions generally contain about 0.1 to about 50 parts active ingredient, about 0.25 to about 50 parts carrier, and about 0 to about 94 parts surface active agent, all parts being by weight based on the total weight of the composition. Similarly, the concentrated compositions typically include about 40 to about 95 parts active ingredient, about 5 to about 25 parts carrier, and about 0 to about 20 parts surface active agent. Emulsifications are usually solutions pesticides in water-immiscible or partially water-immiscible solvents as the carrier together with at least one surface active agent. Suitable solvents for the active ingredients of this invention include, but are not limited to, hydrocarbons and water-immiscible ethers, esters or ketones. The emulsification compositions generally contain from 5 to 95%, preferably 20 to 70% by weight of the active compound of this invention as active ingredient; 1 to 40%, preferably 5 to 20% by weight of surfactant; and 4 to 94%, preferably 10 to 75% by weight of liquid carrier. The compounds useful in the present invention may be readily synthesized using techniques generally known to synthetic organic chemists. Certain nitroethane compounds and their methods of making are disclosed in EP 1000934, which is incorporated by reference in its entirety for all purposes. In particular, the compounds of formula I may be produced by reacting a l-aryl-2-nitroethylene compound of formula II with a substituted thiol compound having the formula UI and a base in the presence of a solvent. The resulting compound may then be oxidized with, for example a conventional oxidizing agent such as 3-chloroperoxybenzoic acid in the presence of a solvent as shown in Flow Diagram I.

Flow Diagram I

(II) (IE) (l) when m= 0 (I)

The present compositions may be prepared in a known manner, for example by homogeneously mixing or grinding the active ingredient(s) with other ingredients. Additional components may be admixed with the composition at any point during the process, including during and/or after any mixing step of the components.

Experimental:

The following examples are put forth so as to provide those of ordinary skill in the art with a complete disclosure and description of how the compounds, compositions, and methods claimed herein are made and evaluated, and are intended to be purely exemplary of the invention and are not intended to limit the scope of what the inventors regard as their invention. Efforts have been made to ensure accuracy with respect to numbers (e.g., amounts, temperature, etc.) but some errors and deviations should be accounted for. Unless indicated otherwise, percent is percent by weight given the component and the total weight of the composition, temperature is in °C or is at ambient temperature, and pressure is at or near atmospheric.

Example 1: Preparation of Test Compounds

Preparation A

(Ai) (AΠ)

At room temperature the thiol compound of formula (AI) (0.20g, 2.0 mmol) was added to a mixture of the nitrostyrene (0.386g, 2.0 mmol) and polystyrene bound diisopropylamine (0.10g) in 10 ml of THF. The reaction was stirred for 18 hours and filtered to remove the resin. The reaction was then treated with l.Og of silica gel and concentrated to dryness. The residue was purified by flash column chromatography (30% Et₂O in hexane) to give 0.46g of product having formula (AU) (77% yield).

All coupling to nitrostyrenes used this procedure unless otherwise stated.

Preparation B

(BI) (BE)

The nitrostyrene of formula (BI) (l.OOg, 6.71 mmol) and the hydroxylamine (0.81g, 7.38 mmol) were added to a solution of NaHCO₃ (0.3 lg, 3.69 mmol) and 10 ml of ethanol. The reaction was refluxed for 18 hours. After cooling, 3.0g of silica gel were added and the reaction was concentrated under reduced pressure. The product of formula (BH) was then purified by flash column chromatography to give the product in 39% yield (0.62g).

Preparation C

C

(ci) (cπ)

The compound of formula (CI) (2.0g, 12.2 mmol), Triton B (0.20 ml) and thiol (1.29g, 12.2 mmol) were added in succession to 10 ml of tetrahydrafuran. The reaction was stirred for 5 days. Silica gel (6.0g) was then added and the reaction mixture concentrated under reduced pressure. The crude product of formula (Cu) was purified by flash chromatography (10-40% on Et₂O in hexane) to give 1.45 grams (44% yield) of the desired material.

Preparation D

(DI) (DE)

The compound of formula (DI) (0.50g, 2.79 mmol) was added to a flask containing 10 ml of THF and the carbazate (0.29g, 2.79 mmol) along with 0.20g of resin bound diisopropylethyl amine. The flash was heated at 45 °C for 18 hours. After cooling silica gel (1.5g) was added and the mixture concentrated under reduced pressure. The product was purified by flash column chromatography to give the desired compound of formula (OIL) in 66% yield (0.52g). Preparation E

(ED (EΠ)

At 0°C ZnCl₂ (3.30g, 24.22 mmol) was added to a flask containing the compound of formula (El) (l.OOg. 6.06 mmol) and the thiol (4.21g, 39.7 mmol). The reaction was warmed to room temperature and stirred overnight. It was then poured into 100 ml of ice water and extracted with CH₂C1₂ (2X50ml). The organic layers were combined, dried over anhydrous Na₂SO and concentrated under reduced pressure. The residue was purified by flash column chromatography (25-50% Et₂O in hexane) to give the desired product of formula (Em) in 65% yield (1.40g).

Mixture of Isomers (EE) (BUT) At 0°C AICI₃ (1.17 g, 8.79 mmol) was added to the compound of formula (EE)

(lOOg, 2.78 mmol) in 10 ml of CH₂C1₂. The reaction was warmed to room temperature and stirred overnight. The reaction was diluted with 100 ml of saturated NH CI solution and 100 ml of CH₂C1₂ and separated. The water layer wash was extracted 2X50ml CH₂C1₂. All organic layers were combined and dried over anhydrous Na₂SO₄. The solvent was removed under reduced pressure and the remaining residue purified by flash column chromatography (35% Et₂O in hexane) to give the desired product of formula (EIE) in 45% yield (0.32g). Following substantially the same procedure as that described for the Preparations A-EE, but using the appropriately substituted compounds, the compounds described in Table 1 were obtained as outlined below. Preparation Compound No.

Preparation A: 1-33, 45-49, 61, 63 and 64 Preparation B: 34-43 and 62 Preparation C: 44 and 50-52 Preparation D: 56-60 Preparation El: 55 Preparation EE: 53 and 54

Table 1: Test Compounds Prepared

Example 2: In Vivo and In Vitro Fungicidal Evaluation of Test Compounds Test compounds were prepared and formulated into aqueous formulations using acetone. These formulations were tested using various target species and the results were evaluated for fungicidal activity as shown in Table 2c.

A. In Vivo Testing

The following leaf disk test method was used to evaluate the in vivo targets of Cucumber Downy Mildew (Pseudoperonospora cubensis) (CDM) and Cucumber

Powdery Mildew (Sphaerotheca fuliginea) (CPM):

Testing Procedures for Leaf Disk Tests

Cucumber seeds were planted (3 per pot) in 3" square plastic pots and maintained in a greenhouse. After emergence, the plants were thinned to 2 per pot and the pots were spaced approximately 3" apart. The plants were grown for a total of 3-4 weeks prior to use.

Cell- well plates were filled with deionized water. Test compounds were formulated in 100% acetone and added to the microplates to achieve the desired final concentration. 12-mm diameter disks were cut from fully expanded leaves of cucumber plants and floated on the surface of chemical solutions.

Leaf disks were oriented with the abaxial (lower) leaf surface upward for the CDM (cucumber downy mildew) assay, and with the adaxial (upper) leaf surface upward for the CPM (cucumber powdery mildew) assay. The plates were stored under laboratory conditions overnight prior to inoculation. Leaf disks for the CPM assay were inoculated by dislodging spores from 2-3 heavily infected leaves onto each plate, which had been placed at the base of a 1-2 foot settling tower. Leaf disks for the CDM assay were inoculated by spraying plates with a suspension of sporangia of the downy mildew pathogen. Approximately 2 ml were applied to each plate.

Water was atomized onto the under-surface of plate covers prior to closure to ensure high humidity during the infection period. Plates for both leaf disk assays were covered and placed in closed polycarbonate boxes. CDM plates were maintained in darkness for 24-48 hours. CPM plates were maintained in darkness for 8-24 hours. The plates were then moved into incubators set for 21 ± 2°C. Illumination was provided by fluorescent lights programmed for a sixteen-hour photo period.

Disease control and phototoxicity were assessed visually 8-10 days following inoculation for CPM, and 5-10 days for CDM using the following rating scales:

Disease Control

Rating % Control

0 0

1 1-14 2 15-29

3 30-44

4 45-59

5 60-74

6 75-89 7 90-95

8 96-99

9 100

Rating not possible Phototoxicity (type)

Code Description

B Bleaching

C Chlorosis

E Edema (water-soaked)

F Formative H Green halo

N Necrosis

Z Bronzing

Additional notes are recorded using the following codes:

t Target not available

X Data not available

L Restricted lesion

R Reduced sporulation

B. In Vitro Testing

The following test method was used to evaluate the in vitro targets of Botrytis cinerea, in vitro (BOTRCI) and Rhizoctonia solani, in vitro (RHTZSO):

The in vitro screen measured the inhibition of mycelial growth in liquid culture. Microtiter plates were filled with a suspension of fungal spores or a ground fungal mycelium in a growth medium. Test materials were dissolved in acetone and added to individual cell wells. A single replicate was used for each test material/dose x pathogen combination. In addition, a solvent blank, reference standard and three untreated, inoculated controls were prepared. After 3-7 days incubation, inhibition of mycelial growth was recorded using the following scales:

Table 2b 1 : Degrees Inhibition for in vitro

Rating Degree of Inhibition

0 None 3 Slight

5 Moderate

7 Severe

9 Complete

Rating not possible Table 2b2: Additional notes for in vitro:

Rating Description t Target not available

X Data not available a Altered morphology

P Pigmentation change r Reduced density Growth stimulation

# Additional observation

Table 2c: Example 2 Experimental Results

Example 3: In Vivo and In Vitro Fungicidal Evaluation of Test Compounds

Test compounds were prepared and formulated into aqueous formulations using acetone. These formulations were tested using various target species and the results were evaluated for fungicidal activity as shown in Table 3. The same in vivo and in vitro rating scales and in vitro test procedures were employed as in Example 2.

In vivo test procedures

Plants were grown in small plastic pots containing commercially prepared potting media in a greenhouse maintained at 20-30 degrees Centigrade. Pots were overhead watered and fertilized once per week with water-soluble fertilizer. Formulated test materials were applied to plants using an automated spray chamber designed to provide uniform coverage of all plant surfaces. When test materials were in limited supply, plants were hand-treated. A single replicate of each test material/dose x plant disease combination was treated. In addition, a solvent blank, a reference standard for each disease target, and three non-treated, inoculated controls were prepared. Plants were dried for 1-3 hours prior to inoculation. For most diseases, pathogen propagules (spores) were suspended in an aqueous carrier and the concentration was adjusted to a specific value. The resulting suspensions were sprayed onto plant surfaces, and the plants were placed in cabinets where relative humidity was maintained near 100% to ensure infection. After 1-7 days, plants were moved to greenhouses where symptoms developed within 2-21 days. Disease control was evaluated visually and recorded using the following scales:

The following fungi assays were used to evaluate the in vivo results:

Apple Scab (Venturia inaequalis) (AS) Grape Downy Mildew (Plasmopara viticold) (GDM)

Pepper Botrytis (Botrytis cinerea) (PB)

Rice Blast (Pyricularia grisea f.sp. oryzae) (RB)

Rice Sheath Blast (Rizoctonia solani AG-I IA) (RSB)

Tomato Early Blight (Alternaria solani) (TEB) Wheat Eyespot (Pseudocercosporella herpotrichoides) (WES)

Wheat Powdery Mildew (Blumeria graminis f.sp. tritci) (WPM)

Wheat Septoria Nodorum Leaf Blotch (Phaeosphaeria (Septoria) nodorum) (WSN) The following fungi assays were used to evaluate the in vitro results:

Alternaria solani, in vitro (ALTESO) Botrytis cinerea, in vitro (BOTRCI)

Fusarium oxysporum f.sp. cucumerinum, in vitro (FUSOXC) Phaeosphaeia (Septoria) nodorum, in vitro (PHAENO) Phytophthora infestans, in vitro (PHYTIN) Pseudocercosporella herpotrichoides, in vitro (PSDCHE) Pythium ultimum, in vitro (PYTHUL) Rhizoctonia solani, in vitro (RHIZSO)

Table 3: Example 3 Experimental Results

Example 4: Nematicidal Evaluation of Test Compounds

Test compounds were prepared and formulated into aqueous formulations using acetone. These formulations were tested using various target species and the results were evaluated for nematicidal activity as shown in Table 4c. a. The following test method was used to evaluate the results on the root-knot nematode (Meloidogyne incognita) (RKN).

Tomato plants (var. Bonny Best) were grown in the greenhouse in large plastic tubs (4 to 6 plants per tub). The plants and soil (a 50:50 mixture of sand and "New Egypt" sandy loam) were infested with M. incognita J2 (to establish the "in-house" colony, RKN were initially acquired from Auburn University). The plants were kept pruned and were used on an "as needed" basis. The plants were watered twice daily and fertilized once a month. Infested plants were brought into the nematode lab and put into a hydroponic culture system. The hydroponic culture system was made of a two-liter glass cylinder with a funnel attached to the end via a plastic connector. A piece of tygon tubing was attached to the end of the funnel with a two-way stopcock. The hydroponic solution was a modified Hoagland solution.

The tomato plants were kept in the cylinder containing hydroponic solution and aerated until the nematodes were no longer present in the solution (usually about 60 days). The cultures were checked daily by eluting a small volume (approximately 20 ml) from the bottom of the funnel apparatus into a small crystallizing dish and observed using a binocular dissecting scope.

If needed for testing, the nematodes were cleaned and concentrated by pouring the culture solution through a sieve for cleaning and a sieve for concentrating. The nematodes were then resuspended, using water, to a concentration of approximately 20 to 50 nematodes per 50 μl. These were counted by putting 25 μl of the nematode solution into a well of an unused well of an assay plate. The total was then multiplied by 2 for a final total of nematodes per 50 μl of solution. To microtiter plates containing about 1.0 mg of compound, 80:20 acetone was added to each well and the solution was mixed to obtain the desired compound concentration. The nematode solution was added to each plate. The plates were then sealed and they were placed in an incubator at 27° C and 50% (+/- 2%) relative humidity. After 72 hours, the test was read using the following scale:

Table 4a: RKN Rating System

9 — total/near total population mortality (-95 to 100%) 5 — moderate population mortality (-40 to 80%) 0 — none/nil population mortality (<25%) mortality = immobility

b. The following test method was used to evaluate the results on the soybean cyst nematode (Heterodera glycine (SCN): Soybean bean cyst nematode culture was maintained in a greenhouse and soybean eggs and J2 larvae were obtained for testing by dislodging soybean cysts from the roots with a sieve. The cysts were broken to release the eggs and the eggs were maintained in water. The eggs hatched after 5-7 days at 28°C.

To microtiter plates containing about 150 μg of compound, 80:20 acetone was added to each well and the solution was mixed to obtain the desired compound concentration. The nematode solution was added to the plate. The plates were then sealed and placed in an incubator at 27°C and 50% (+/-2%) relative humidity. After 72 hours, the test was read using the following scale:

Table 4b: SCN Rating System

9 - total/near total population mortality (-95 to 100%)

5 - moderate population mortality (-40 to 80%)

0 - none/nil population mortality (<25%) mortality = immobility

Table 4c: Example 4 Experimental Results

Throughout this application, various publications are referenced. The disclosures of these publications in their entireties are hereby incorporated by reference into this application for all purposes.

It will be apparent to those skilled in the art that various modifications and variations can be made in the present invention without departing from the scope or spirit of the invention. Other embodiments of the invention will be apparent to those skilled in the art from consideration of the specification and practice of the invention disclosed herein. It is intended that the specification and examples be considered as exemplary only, with a true scope and spirit of the invention being indicated by the following claims.

Claims

What is claimed is:

1. A compound of formula I:

(I) wherein:

A is hydrogen or X(O)_mR,

Ar is phenyl unsubstituted or substituted 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 Cι-C₄ haloalkyl groups, one to three CrC alkoxy groups, one to three Ci-C₄ haloalkoxy groups, one to three Cχ-C₄ alkylthio groups, one to three C C₄ haloalkylthio groups, one benzylthio group or one SCH₂C0₂R₂ group,

1- or 2-naphthyl unsubstituted or substituted with any combination of one to five halogen atoms, one or two cyano groups, one or two nitro groups, one to three Cι-C₄ alkyl groups, one to three C C₄ haloalkyl groups, one to three C]-C₄ alkoxy groups, one to three Cι-C₄ haloalkoxy groups, one to three Cι-C₄ alkylthio groups or one to three -C₄ haloalkylthio groups,

piperonyl unsubstituted or substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three -Q. alkyl groups, one to three C C haloalkyl groups, one to three -Gt alkoxy groups, one to three C C₄ haloalkoxy groups, one to three Cι-C₄ alkylthio groups or one to three -C₄ haloalkylthio groups, 2-, 3- or 4-pyridyl unsubstituted or substituted with any combination of one to four halogen atoms, one or two cyano groups, one or two nitro groups, one to three -C₄ alkyl groups, one to three C₁-C₄ haloalkyl groups, one to three C₁-C₄ alkoxy groups, one to three -C₄ haloalkoxy groups, one to three Cι-C₄ alkylthio groups or one to three Cι-C₄ haloalkylthio groups,

2- or 3-furyl unsubstituted or substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three Ci-C₄ alkyl groups, one to three - . haloalkyl groups, one to three - alkoxy groups, one to three - haloalkoxy groups, one to three C;ι-C₄ alkylthio groups or one to three C₁-C₄ haloalkylthio groups, or

2- or 3-thienyl unsubstituted or substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three Cι-C₄ alkyl groups, one to three C₁-C haloalkyl groups, one to three -C alkoxy groups, one to three -C₄ haloalkoxy groups, one to three - alkylthio groups or one to three C₁-C₄ haloalkylthio groups;

is hydrogen, C₁-C₄ alkyl, Ci-C₄ alkoxy, C_Ϊ-C haloalkyl, C₂-C₄ alkenyl, C₂

-C₄ haloalkenyl, CR R₅CO₂R₃, (CH₂)_nNO₂, CR₅R₆CONR₇R₈, NR₅CO₂R₃, or O(CH₂)_nCO₂R₃;

is hydrogen, -Gj. alkyl, (CH₂)CN, or phenyl unsubstituted or substituted with any combination of one to five halogen atoms, one or two cyano groups, one or two nitro groups, one to three Ci-C₄ alkyl groups, one to three Cι-C haloalkyl groups, one to three Cι-C₄ alkoxy groups, one to three -C₄ haloalkoxy groups, one to three C₁-C alkylthio groups or one to three C C haloalkylthio groups; R₂, R₃, R₄, R₅, R₆, R₇ and R₈ are each independently hydrogen, Cι-C₁₀ alkyl, (d-

Cio haloalkyl), C₂-C₁₀ alkenyl, C₂-C₁₀ haloalkenyl,

benzyl unsubstituted or 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 C C₄ alkyl groups, one to three Cι-C₄ haloalkyl groups, one to three -C alkoxy groups, one to three C C₄ haloalkoxy groups, one to three C]-C₄ alkylthio groups or one to three Cι-C₄ haloalkylthio groups, or

phenyl unsubstituted or substituted with any combination of one to five halogen atoms, one or two cyano groups, one or two nitro groups, one to three Cι-C alkyl groups, one to three C C₄ haloalkyl groups, one to three C C₄ alkoxy groups, one to three C₁-C₄ haloalkoxy groups, one to three C C₄ alkylthio groups or one to three C₁-C₄ haloalkylthio groups;

k is 1 or 2, provided that if I is 0 then k is 1 and is double-bonded to C

I is 0 or 1, provided that if k is 1 then / is 0 and d is double-bonded to C

m is 0, 1 or 2;

n is O, 1, or 2;

Y is NO₂ or CN; and

X is NR₅ or S;

or salts, radicals or esters thereof; provided that when X is S and Y is NO₂, R is other than hydrogen, - alkyl, C C₄ haloalkyl, C₂-C alkenyl, or C₂ -C₄ haloalkenyl or a radical CR₄R₅CO₂R₃, wherein both R₄ and R₅ are H.

2. The compound as claimed in claim 1, wherein A is hydrogen;

Ri is hydrogen; k is 2 and l is 1.

3. The compound as claimed in claims 1 or 2, wherein Ar is phenyl which is unsubstituted or substituted as defined above, piperonyl, which is unsubstituted or substituted as defined above, or 2- or 3-thienyl, which is unsubstituted or carries one halogen atom.

4. The compound as claimed in any of the preceding claims, wherein R is selected from Q- C₄-alkoxy, CH₂CN, CH₂CH₂NO₂, CR_4aR₅CO₂R₃, wherein R _a has the meanings given for R⁴ but is different from H, CR₅R₆CONR₇R₈, NR₅CO₂R₃, or O(CH₂)_nCO₂R₃ with n being l or 2.

5. The compound as claimed in any of the preceding claims, wherein the variables X(O)_m and R together form a group NR_5a-C₁-C₄-alkoxy, SCH₂CN, SCH₂CH₂NO₂, SCR _aR₅CO₂R₃, wherein R_4a has the meanings given for R⁴ but is different from H, SCR₅R₆CONR₇R₈, NR_5aNR_5bCO₂R₃, or NR_5aO(CH₂)_nCO₂R₃ with n being 1 or 2, wherein R^5a and R^5b are as defined for R⁵.

6. The compound as claimed in any of the preceding claims, wherein Y is NO₂.

7. The compound as claimed in claim 1, selected from: 2-[l-(4-Methoxy-phenyl)-2-nitro- ethylsulf anyl] -propionic acid; 2-(2-Nitro-l -phenyl -ethylsulfanyl)-propionic acid; 2-(l- Benzo[l,3]dioxol-5-yl-2-nitro-ethylsulfanyl)-propionic acid; 2-(2-Nitro-l-p-tolyl- ethylsulfanyl)-propionic acid; 2-(2-Nitro-l -phenyl-ethylsulf anyl)-propionic acid ethyl ester; 2-[l-(4-Methoxy-phenyl)-2-nitro-ethylsulfanyl]-propionic acid ethyl ester; 2-(l- Benzo[l,3]dioxol-5-yl-2-nitro-ethylsulfanyl)-propionic acid ethyl ester; 2-(2-Nitro-l-p- tolyl-ethylsulfanyl)-propionic acid ethyl ester; (2-Nitro- 1 -phenyl-ethylsulf anyl)- acetonitrile; ( 1 -Benzo[ 1 ,3]dioxol-5-yl-2-nitro-ethylsulfanyl)-acetonitrile; (2-Nitro-l -p- tolyl-ethylsulf anyl)-acetonitrile; 2-Methyl-2-(2-nitro- 1 -phenyl-ethylsulf anyl)-propionic acid; 2-[l-(4-Methoxy-phenyl)-2-nitro-ethylsulfanyl]-2-methyl-propionic acid; 2-(l-

Benzo[l ,3]dioxol-5-yl-2-nitro-ethylsulfanyl)-2-methyl-propionic acid; 2-Methyl-2-(2- nitro- 1 -p-tolyl-ethylsulf anyl)-propionic acid; 2-[ 1 -(4-Huoro-phenyl)-2-nitro- ethylsulf anyl] -propionic acid; 2-[l-(4-Fluoro-phenyl)-2-nitro-ethylsulfanyl]-propionic acid ethyl ester; 2-[l-(4-Fluoro-phenyl)-2-nitro-ethylsulfanyl]-2-methyl-propionic acid;

N,N-Dimethyl-2-(2-nitro-l-phenyl-ethylsulfanyl)-acetamide; 2-[l-(4-Methoxy-phenyl)-

2-nitro-ethylsulfanyl]-N,N-dimethyl-acetamide; 2-(l-Benzo[l,3]dioxol-5-yl-2-nitro- ethylsulfanyl)-N,N-dimethyl-acetamide; N,N-Dimethyl-2-(2-nitro-l-p-tolyl- ethylsulfanyl)-acetamide; 2-[l-(4-Fluoro-phenyl)-2-nitro-ethylsulfanyl]-N,N-dimethyl- acetamide; N,N-Diethyl-2-(2-nitro- 1 -phenyl-ethylsulf anyl)-acetamide; N,N-Diethyl-2- [1 -

(4-methoxy-phenyl)-2-nitro-ethylsulfanyl]-acetamide; 2-(l~Benzo[l,3]dioxol-5-yl-2- nitro-ethylsulfanyl)-N,N-diethyl-acetamide; N,N-Diethyl-2-(2-nitro-l-p-tolyl- ethylsulfanyl)-acetamide; N,N-Diethyl-2-[l-(4-fluoro-phenyl)-2-nitro-ethylsulfanyl]- acetamide; [2-Nitro- 1 -(2-nitro-ethylsulfanyl)-ethyl] -benzene; 1 -Methoxy-4- [2-nitro- 1 -(2- nitro-ethylsulfanyl)-ethyl]-benzene; 5-[2-Nitro-l-(2-nitro-ethylsulfanyl)-ethyl]- benzo[l,3]dioxole; l-Methyl-4-[2-nitro-l-(2-nitro-ethylsulfanyl)-ethyll-benzene; 1-

Fluoro-4-[2-nitro-l-(2-nitro-ethylsulfanyl)-ethyl]-benzene; O-Ethyl-N-(2-nitro-l-phenyl- ethyl)-hydroxyl amine ; O-Ethyl-N- [ 1 -(4-methoxy-phenyl)-2-nitro-ethyl] -hydroxyl amine ;

N-(l-Benzo[l,3]dioxol-5-yl-2-nitro-ethyl)-O-ethyl-hydroxylamine; O-Ethyl-N-(2-nitro-

1 -p-tolyl-ethyl)-hydroxylamine; O-Ethyl-N- [ 1 -(4-fluoro-phenyl)-2-nitro-ethyl] - hydroxylamine; [N-(2-Nitro-l-phenyl-ethyl)aminooxy]-acetic acid; {N-[l-(4-Methoxy- phenyl)-2-nitro-ethyl] aminooxy} -acetic acid; [N-(l-Benzo[l,3]dioxol-5-yl-2-nitro- ethyl)aminooxy]-acetic acid; [N-(2-Nitro-l-p-tolyl-ethyl)aminooxy]-acetic acid; {N-[l-

(4-Fluoro-phenyl)-2-nitro-ethyl] aminooxy } -acetic acid; [ 1 -(4-Chloro-phenyl)-2-cyano- ethylsulfanyl]-acetic acid methyl ester; [N-(2-Nitro-l -phenyl -ethyl)aminooxy]-acetic acid methyl ester; {N-[l-(4-Methoxy-phenyl)-2-nirro-ethyl]aminooxy}-acetic acid methyl ester; [N-(l-Benzo[l,3]dioxol-5-yl-2-nitro-ethyl)aminooxy]-acetic acid methyl ester; [N-

(2-Nitro-l-p-tolyl-ethyl)aminooxy]-acetic acid methyl ester; {N-[l-(4-Fluoro-phenyl)-2- nitro-ethyl] aminooxy} -acetic acid methyl ester; [2-Cyano- l-(4-methoxy-phenyl)- ethylsulfanyl]-acetic acid methyl ester; [2-Cyano- 1 -(3, 4-dimethoxy-phenyl)- ethylsulfanyl]-acetic acid methyl ester; (2-Cyano- 1 -phenyl -ethylsulfanyl)-acetic acid methyl ester; N'-(2-Nitro-l-ρhenyl-ethyl)-hydrazinecarboxylic acid ethyl ester; N'-[l-(4-

Fluoro-phenyl)-2-nitro-ethyl]-hydrazinecarboxylic acid ethyl ester; N'-(2-Nitro-l-p-tolyl- ethyl)-hydrazinecarboxylic acid ethyl ester; N'-(l-Benzo[l,3]dioxol-5-yl-2-nitro-ethyl)- hydrazinecarboxylic acid ethyl ester; N'-[l-(4-Methoxy-phenyl)-2-nitro-ethyl]- hydrazinecarboxylic acid ethyl ester; 2-[l-(4-Bromo-thiophen-2-yl)-2-nitro- ethylsulf anyl] -propionic acid; { N-[ 1 -(4-Bromo-thiophen-2-yl)-2-nitro-ethyl] aminooxy } - acetic acid; 2-[l-(4-Bromo-thiophen-2-yl)-2-nitro-ethylsulfanyl]-N,N-diethyl-acetamide;

4-Bromo-2-[2-nitro-l-(2-nitro-ethylsulfanyl)-ethyl]-thiophene; 2-[l-(4-Bromo-thiophen-

2-yl)-2-nitro-ethylsulfanyl]-propionic acid; or 4-Bromo-2- [2-nitro- l-(2-nitro- ethylsulfanyl)-ethyl]-thiophene.

8. An agricultural composition comprising, in addition to at least one compound of formula (I) as claimed in claim 1 or its salt, an agronomically acceptable carrier.

9. A method of protecting crops from attack by nematodes comprising treating a crop with a pesticidally effective amount of a compound of formula (I) or a salt as claimed in any of the claims 1 to 7.

10. The method of claim 9, wherein the compound of formula (I) is: 2-(2-Nitro-l-phenyl- ethylsulfanyl)-propionic acid; 2-(l-Benzo[l,3]dioxol-5-yl-2-nitro-ethylsulfanyl)- propionic acid; 2-(2-Nitro-l-p-tolyl-ethylsulfanyl)-propionic acid; 2-(2-Nitro-l -phenyl - ethylsulfanyl)-propionic acid ethyl ester; 2-[l-(4-Methoxy-phenyl)-2-nitro- ethylsulf anyl] -propionic acid ethyl ester; 2-(l-Benzo[l,3]dioxol-5-yl-2-nitro- ethylsulfanyl)-propionic acid ethyl ester; 2-(2-Nitro-l-p-tolyl-ethylsulfanyl)-propionic acid ethyl ester; (l-Benzo[l,3]dioxol-5-yl-2-nitro-ethylsulfanyl)-acetonitrile; (2-Nitro- 1- p-tolyl-ethylsulfanyl)-acetonitrile; 2-[l-(4-Methoxy-phenyl)-2-nitro-ethylsulfanyl]-N,N- dimethyl-acetamide; 2-(l-Benzo[l,3]dioxol-5-yl-2-nitro-ethylsulfanyl)-N,N-dimethyl- acetamide; N,N-Dimethyl-2-(2-nitro- 1 -p-tolyl-ethylsulfanyl)-acetamide; N,N-Diethyl-2- (2-nitro-l-phenyl-ethylsulfanyl)-acetamide; N,N-Diethyl-2-[l-(4-methoxy-phenyl)-2- nitro-ethylsulf anyl] -acetamide; N,N-Diethyl-2-(2-nitro- 1 -p-tolyl-ethylsulf anyl)- acetamid; [2-Nitro- 1 -(2-nitro-ethylsulf anyl)-ethyl] -benzene; 1 -Methoxy-4- [2-nitro- 1 -(2- nitro-ethylsulfanyl)-ethyl]-benzene; 5-[2-Nitro-l-(2-nitro-ethylsulfanyl)-ethyl]- benzo[l,3]dioxole; {N-[l-(4-Methoxy-phenyl)-2-nitro-ethyl] aminooxy} -acetic acid; [N-

(l-Benzo[l,3]dioxol-5-yl-2-nitro-ethyl)aminooxy]-acetic acid; {N-[l-(4-Fluoro-phenyl)-

2-nitro-ethyl] aminooxy } -acetic acid; [N-( 1 -Benzo[ 1 ,3]dioxol-5-yl-2-nitro- ethyl)aminooxy]-acetic acid methyl ester; 2-[l-(4-Bromo-thiophen-2-yl)-2-nitro- ethylsulf anyl] -propionic acid; or 2-[l-(4-Bromo-thiophen-2-yl)-2-nitro-ethylsulfanyl]-

N,N-diethyl-acetamide.

11. The method of claim 10, wherein the compound of formula (I) is: 2-(2-Nitro-l-phenyl- ethylsulfanyl)-propionic acid; 2-[l -(4-Methoxy-phenyl)-2-nitro-ethylsulfanyl]-N,N- dimethyl-acetamide; N,N-Dimethyl-2-(2-nitro- l-p-tolyl-ethylsulfanyl)-acetamide; N,N- Diethyl-2-(2-nitro-l-p-tolyl-ethylsulfanyl)-acetamide; [2-Nitro- l-(2-nitro-ethylsulfanyl)-, ethyl] -benzene; 1 -Methoxy-4- [2-nitro- 1 -(2-nitro-ethylsulf anyl)-ethyl] -benzene; 5-[2- Nitro-l-(2-nitro-ethylsulfanyl)-ethyl]-benzo[l,3]dioxole; or [N-(l-Benzo[l,3]dioxol-5-yl- 2-nitro-ethyl)aminooxy]-acetic acid.

12. A method for controlling fungus, comprising treating fungus with a pesticidally effective amount of a compound of formula (I)

(I) wherein:

A is hydrogen or X(O)_mR,

Ar is phenyl unsubstituted or substituted with any combination of one to five halogen atoms, one or two cyano groups, one or two nitro groups, one to three Q-Q alkyl groups, one to three C C₄ haloalkyl groups, one to three Cι-C₄ alkoxy groups, one to three C]-C₄ haloalkoxy groups, one to three

Cι-C₄ alkylthio groups, one to three Cι-C₄ haloalkylthio groups, one benzylthio group or one SCH₂C0₂R₂ group,

1- or 2-naphthyl unsubstituted or substituted with any combination of one to five halogen atoms, one or two cyano groups, one or two nitro groups, one to three Cι-C₄ alkyl groups, one to three C₁-C₄ haloalkyl groups, one to three C C₄ alkoxy groups, one to three -C₄ haloalkoxy groups, one to three C₁-C₄ alkylthio groups or one to three C₁-C₄ haloalkylthio groups,

piperonyl unsubstituted or substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three Q-C₄ alkyl groups, one to three Cι-C₄ haloalkyl groups, one to three C C₄ alkoxy groups, one to three C C₄ haloalkoxy groups, one to three Cι-C₄ alkylthio groups or one to three C₁-C₄ haloalkylthio groups,

2-, 3- or 4-pyridyl unsubstituted or substituted with any combination of one to four halogen atoms, one or two cyano groups, one or two nitro groups, one to three Cι-C alkyl groups, one to three C₁-C₄ haloalkyl groups, one to three Q-C₄ alkoxy groups, one to three C1-C₄ haloalkoxy groups, one to three - alkylthio groups or one to three C₁-C₄ haloalkylthio groups,

2- or 3-furyl unsubstituted or substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three C -C₄ alkyl groups, one to three Ci-C₄ haloalkyl groups, one to three C₁-C₄ alkoxy groups, one to three C₁-C4 haloalkoxy groups, one to three Cι-C₄ alkylthio groups or one to three C₁-C₄ haloalkylthio groups, or

2- or 3-thienyl unsubstituted or substituted with any combination of one to three halogen atoms, one or two cyano groups, one or two nitro groups, one to three CrC₄ alkyl groups, one to three C₁-C₄ haloalkyl groups, one to three Cι-C₄ alkoxy groups, one to three Cι-C haloalkoxy groups, one to three C C₄ alkylthio groups or one to three CrC₄ haloalkylthio groups;

R is hydrogen, C C₄ alkyl, - alkoxy, C C₄ haloalkyl, C -C₄ alkenyl, C₂ -C₄ haloalkenyl, CR₄R₅CO₂R₃, (CH₂)_nNO₂, CR₅R₆CONR₇R₈, NR₅CO₂R₃, or O(CH₂)_nCO₂R₃;

Ri is hydrogen, C C₄ alkyl, (CH₂)CN, or phenyl unsubstituted or substituted with any combination of one to five halogen atoms, one or two cyano groups, one or two nitro groups, one to three C C₄ alkyl groups, one to three CrC₄ haloalkyl groups, one to three -Q. alkoxy groups, one to three C1-C₄ haloalkoxy groups, one to three Cι-C₄ alkylthio groups or one to three Cι-C₄ haloalkylthio groups;

R₂, R₃, R₄, R₅, R₆, R₇ and R₈ are each independently hydrogen, - o alkyl, (Q- C_IQ haloalkyl), C2- ₀ alkenyl, C -Cι₀ haloalkenyl,

benzyl unsubstituted or 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 C Q. alkyl groups, one to three Q-Q. haloalkyl groups, one to three -C₄ alkoxy groups, one to three -C4 haloalkoxy groups, one to three Q-C₄ alkylthio groups or one to three Cι-C₄ haloalkylthio groups, or

phenyl unsubstituted or substituted with any combination of one to five halogen atoms, one or two cyano groups, one or two nitro groups, one to three C]-C₄ alkyl groups, one to three -C₄ haloalkyl groups, one to three C₁-C₄ alkoxy groups, one to three - . haloalkoxy groups, one to three -C₄ alkylthio groups or one to three C₁-C₄ haloalkylthio groups; k is 1 or 2, provided that if I is 0 then k is 1 and is double-bonded to C₂

I is 0 or 1, provided that if k is 1 then / is 0 and is double-bonded to C₂

m is 0, 1 or 2;

n is O, 1, or 2;

Y is NO₂ or CN; and

X is NR₅ or S;

or salts, radicals or esters thereof.

13. The method as claimed in claim 12, wherein A is hydrogen;

Ri is hydrogen; k is 2 and l is 1.

14. The method as claimed in claims 12 or 13, wherein Ar is phenyl which is unsubstituted or substituted as defined above, piperonyl, which is unsubstituted or substituted as defined above, or 2- or 3-thienyl, which is unsubstituted or carries one halogen atom.

15. The method as claimed in any of the claims 12 to 14, wherein R is selected from C₁-C₄- alkoxy, CH CN, CH CH₂NO₂, CR _aR₅CO₂R₃, wherein R_4a has the meanings given for R⁴ but is different from H, CR₅R₆CONR₇R₈, NR₅CO₂R₃, or O(CH₂)_nCO₂R₃ with n being 1 or 2.

16. The method as claimed in any of the claims 12 to 15, wherein the variables X(O)_m and R together form a group NR_5a-Cι-C₄-alkoxy, SCH₂CN, SCH₂CH₂NO₂, SCR_4aR₅CO₂R₃, wherein R_4a has the meanings given for R⁴ but is different from H, SCR₅R₆CONR₇R₈, NR_5aNR_5bCO₂R₃, or NR_5aO(CH₂)_nCO₂R₃ with n being 1 or 2, wherein R ₅ ^Da^a and R >₅b are as defined for R⁵.

17. The method as claimed in any of the claims 12 to 16, wherein Y is NO .

18. The method of claim 12, wherein the compound of formula (I) is: 2-[l-(4-Methoxy- phenyl)-2-nitro-ethylsulfanyl]-propionic acid; 2-(2-Nitro- 1 -phenyl-ethylsulfanyl)- propionic acid; 2-(l-Benzo[l,3]dioxol-5-yl-2-nitro-ethylsulfanyl)-propionic acid; 2-(2- Nitro- 1 -p-tolyl-ethylsulfanyl)-propionic acid; 2-(2-Nitro- 1 -phenyl-ethylsulf anyl)- propionic acid ethyl ester; 2-[l-(4-Methoxy-phenyl)-2-nitro-ethylsulfanyl]-propionic acid ethyl ester; 2-(l-Benzo[l,3]dioxol-5-yl-2-nitro-ethylsulfanyl)-propionic acid ethyl ester; 2-(2-Nitro-l -p-tolyl-ethylsulf anyl)-propionic acid ethyl ester; (2-Nitro- 1-phenyl- ethylsulfanyl)-acetonitrile; (l-Benzo[l,3]dioxol-5-yl-2-nitro-ethylsulfanyl)-acetonitrile; (2-Nitro- l-p-tolyl-ethylsulfanyl)-acetonitrile; 2-Methyl-2-(2-nitro-l-phenyl- ethylsulfanyl)-propionic acid; 2-[l-(4-Methoxy-phenyl)-2-nitro-ethylsulfanyl]-2-methyl- propionic acid; 2-(l-Benzo[l,3]dioxol-5-yl-2-nitro-ethylsulfanyl)-2-methyl-propionic acid; 2-Methyl-2-(2-nitro-l -p-tolyl-ethylsulf anyl)-propionic acid; 2-[l-(4-Huoro- phenyl)-2-nitro-ethylsulfanyl]-propionic acid; 2-[l-(4-Fluoro-phenyl)-2-nitro- ethylsulf anyl] -propionic acid ethyl ester; 2-[l-(4-Fluoro-phenyl)-2-nitro-ethylsulfanyl]-2- methyl-propionic acid; N,N-Dimethyl-2-(2-nitro-l-phenyl-ethylsulfanyl)-acetamide; 2-

[ 1 -(4-Methoxy-phenyl)-2-nitro-ethylsulf anyl] -N,N-dimethyl-acetamide; 2-( 1 - Benzo[l,3]dioxol-5-yl-2-nitro-ethylsulfanyl)-N,N-dimethyl-acetamide; N,N-Dimethyl-2- (2-nitro- 1 -p-tolyl-ethylsulfanyl)-acetamide; 2- [ 1 -(4-Fluoro-phenyl)-2-nitro- ethylsulfanyl]-N,N-dimethyl-acetamide; N,N-Diethyl-2-(2-nitro- 1 -phenyl-ethylsulfanyl)- acetamide; N,N-Diethyl-2-[l-(4-methoxy-phenyl)-2-nitro-ethylsulfanyl]-acetamide; 2-(l- Benzo[l,3]dioxol-5-yl-2-nitro-ethylsulfanyl)-N,N-diethyl-acetamide; N,N-Diethyl-2-(2- nitro- 1 -p-tolyl-ethylsulfanyl)-acetamide; N,N-Diethyl-2-[ 1 -(4-fluoro-phenyl)-2-nitro- ethylsulfanyl]-acetamide; [2-Nitro-l-(2-nitro-ethylsulfanyl)-ethyl]-benzene; 1-Methoxy- 4-[2-nitro-l-(2-nitro-ethylsulfanyl)-ethyl]-benzene; 5-[2-Nitro-l-(2-nitro-ethylsulfanyl)- ethyl]-benzo[l,3]dioxole; l-Methyl-4-[2-nitro-l-(2-nitro-ethylsulfanyl)-ethyl]-benzene; l-Fluoro-4-[2-nitro-l-(2-nitro-ethylsulfanyl)-ethyl]-benzene; O-Ethyl-N-(2-nitro-l- phenyl-ethyl)-hydroxylamine; O-Ethyl-N-[l-(4-methoxy-phenyl)-2-nitro-ethyl]- hydroxylamine; N-(l-Benzo[l,3]dioxol-5-yl-2-nitro-ethyl)-O-ethyl-hydroxylamine; O-

Ethyl-N-(2-nitro-l-p-tolyl-ethyl)-hydroxylamine; O-Ethyl-N-[l-(4-fluoro-phenyl)-2- nitro-ethyl] -hydroxyl amine; [N-(2-Nitro-l-phenyl-ethyl)aminooxy] -acetic acid; {N-[l-(4-

Methoxy-phenyl)-2-nitro-ethyl]aminooxy}-acetic acid; [N-(l-Benzo[l,3]dioxol-5-yl-2- nitro-ethyl)aminooxy]-acetic acid; [N-(2-Nitro-l-p-tolyl-ethyl)aminooxy]-acetic acid;

{ N-[ 1 -(4-Fluoro-phenyl)-2-nitro-ethyl] aminooxy } -acetic acid; [1 -(4-Chloro-phenyl)-2- cyano-ethylsulfanyl]-acetic acid methyl ester; [N-(2-Nitro-l-phenyl-ethyl)aminooxy]- acetic acid methyl ester; {N-[l-(4-Methoxy-phenyl)-2-nitro-ethyl]aminooxy}-acetic acid methyl ester; [N-(l-Benzo[l,3]dioxol-5-yl-2-nitro-ethyl)aminooxy]-acetic acid methyl ester; [N-(2-Nitro-l-p-tolyl-ethyl)aminooxy]-acetic acid methyl ester; {N-[l-(4-Fluoro- phenyl)-2-nitro-ethyl] aminooxy} -acetic acid methyl ester; [2-Cyano- l-(4-methoxy- phenyl)-ethylsulfanyl]-acetic acid methyl ester; [2-Cyano- l-(3,4-dimethoxy-phenyl)- ethylsulfanyl]-acetic acid methyl ester; (2-Cyano- l-phenyl-ethylsulfanyl)-acetic acid methyl ester; N'-(2-Nitro-l-phenyl-ethyl)-hydrazinecarboxylic acid ethyl ester; N'-[l-(4-

Fluoro-phenyl)-2-nitro-ethyl] -hydrazinecarboxylic acid ethyl ester; N'-(2-Nitro-l-p-tolyl- ethyl)-hydrazinecarboxylic acid ethyl ester; N'-(l-Benzo[l,3]dioxol-5-yl-2-nitro-ethyl)- hydrazinecarboxylic acid ethyl ester; N'-[l-(4-Methoxy-phenyl)-2-nitro-ethyl]- hydrazinecarboxylic acid ethyl ester; 2-[l-(4-Bromo-thiophen-2-yl)-2-nitro- ethylsulfanyl]-propionic acid; {N-[l-(4-Bromo-thiophen-2-yl)-2-nitro-ethyl]aminooxy}- acetic acid; 2-[l-(4-Bromo-thiophen-2-yl)-2-nitro-ethylsulfanyl]-N,N-diethyl-acetamide;

4-Bromo-2- [2-nitro- 1 -(2-nitro-ethylsulf anyl)-ethyl] -thiophene; 2- [ 1 -(4-Bromo-thiophen-

2-yl)-2-nitro-ethylsulfanyl]-propionic acid; or 4-Bromo-2-[2-nitro-l-(2-nitro- ethylsulfanyl)-ethyl]-thiophene.

19. The method of claim 18, wherein the compound of formula (I) is: 2-(2-Nitro-l-phenyl- ethylsulfanyl)-propionic acid; (l-Benzo[l ,3]dioxol-5-yl-2-nitro-ethylsulfanyl)- acetonitrile; 2-Methyl-2-(2-nitro-l-phenyl-ethylsulfanyl)-propionic acid; 2-Methyl-2-(2- nitro-1 -p-tolyl-ethylsulf anyl)-propionic acid; 2-[l-(4-Fluoro-phenyl)-2-nitro- ethylsulf anyl] -propionic acid; 2-[l-(4-Huoro-phenyl)-2-nitro-ethylsulfanyl]-propionic acid ethyl ester; 2-[l-(4-Fluoro-phenyl)-2-nitro-ethylsulfanyl]-2-methyl-propionic acid; N,N-Diethyl-2-(2-nitro- 1 -p-tolyl-ethylsulf anyl)-acetamide; 1 -Methyl-4- [2-nitro- 1 -(2- nitro-ethylsulf anyl)-ethyl] -benzene; 1 -Fluoro-4- [2-nitro- 1 -(2-nitro-ethylsulf anyl)-ethyl] - benzene; O-Ethyl-N-[l-(4-methoxy-phenyl)-2-nitro-ethyl]-hydroxylamine; O-Ethyl-N-

(2-nitro- 1 -ρ-tolyl-ethyl)-hydroxylamine ; O-Ethyl-N- [ 1 -(4-fluoro-phenyl)-2-nitro-ethyl] - hydroxylamine [N-(2-Nitro-l-p-tolyl-ethyl)aminooxy]-acetic acid; {N-[l-(4-Fluoro- phenyl)-2-nitro-ethyl]aminooxy}-acetic acid; [N-(2-Nitro-l-phenyl-ethyl)aminooxy]- acetic acid methyl ester; {N-[l-(4-Methoxy-phenyl)-2-nitro-ethyl]aminooxy}-acetic acid methyl ester; [N-(l-Benzo[l,3]dioxol-5-yl-2-nitro-ethyl)aminooxy]-acetic acid methyl ester; [N-(2-Nitro-l-p-tolyl-ethyl)aminooxy]-acetic acid methyl ester; {N-[l-(4-Fluoro- phenyl)-2-nitro-ethyl] aminooxy} -acetic acid methyl ester; 2-[l-(4-Bromo-thiophen-2- yl)-2-nitro-ethylsulfanyl]-propionic acid; or {N-[l-(4-Bromo-thiophen-2-yl)-2-nitro- ethyl] aminooxy} -acetic acid.

20. The method of claim 19, wherein the compound of formula (I) is: 2-(2-Nitro-l-phenyl- ethylsulfanyl)-propionic acid; (l-Benzo[l ,3]dioxol-5-yl-2-nitro-ethylsulfanyl)- acetonitrile; N,N-Diethyl-2-(2-nitro-l-p-tolyl-ethylsulfanyl)-acetamide; [N-(2-Nitro-l- p-tolyl-ethyl)aminooxy] -acetic acid methyl ester; { N- [ 1 -(4-Fluoro-phenyl)-2-nitro- ethyl] aminooxy} -acetic acid methyl ester; or2-[l-(4-Bromo-thiophen-2-yl)-2-nitro- ethylsulf anyl] -propionic acid.

21. The method as claimed in any of claims 12 to 20, wherein the compound of formula (I) is applied at a rate of about 50 g per hectare to about 500 g per hectare.

22. A method for controlling nematodes, comprising treating a nematode with a pesticidally effective amount of a compound of formula (I) or its salt as claimed in any of the claims 1 to 7.

23. The method as claimed in claim 22, wherein the compound of formula (I) is: 2-[l-(4- Methoxy-phenyl)-2-nitro-ethylsulfanyl] -propionic acid; 2-(2-Nitro- 1 -phenyl - ethylsulfanyl)-propionic acid; 2-(l-Benzo[l ,3]dioxol-5-yl-2-nitro-ethylsulfanyl)- propionic acid; 2-(2-Nitro-l -p-tolyl-ethylsulf anyl)-propionic acid; 2-(2-Nitro-l-phenyl- ethylsulf anyl)-propionic acid ethyl ester; 2-[l-(4-Methoxy-phenyl)-2-nitro-ethylsulfanyl]- propionic acid ethyl ester; 2-(l-Benzo[l,3]dioxol-5-yl-2-nitro-ethylsulfanyl)-propionic acid ethyl ester; 2-(2-Nitro-l -p-tolyl-ethylsulf anyl)-propionic acid ethyl ester; (2-Nitro-l- ρhenyl-ethylsulfanyl)-acetonitrile; (l-Benzo[l,3]dioxol-5-yl-2-nitro-ethylsulfanyl)- acetonitrile; (2-Nitro- 1 -p-tolyl-ethylsulfanyl)-acetonitrile; 2-Methyl-2-(2-nitro- 1 -phenyl - ethylsulfanyl)-propionic acid; 2-[l-(4-Methoxy-phenyl)-2-nitro-ethylsulfanyl]-2-methyl- propionic acid; 2-(l-Benzo[l ,3]dioxol-5-yl-2-nitro-ethylsulfanyl)-2-methyl-propionic acid; 2-Methyl-2-(2-nitro-l -p-tolyl-ethylsulf anyl)-propionic acid; 2-[l-(4-Huoro- phenyl)-2-nitro-ethylsulf anyl] -propionic acid; 2- [ 1 - (4-Fluoro-phenyl)-2-nitro- ethylsulf anyl] -propionic acid ethyl ester; 2-[l-(4-Huoro-phenyl)-2-nitro-ethylsulfanyl]-2- methyl-propionic acid; N,N-Dimethyl-2-(2-nitro-l-phenyl-ethylsulfanyl)-acetamide; 2- [l-(4-Methoxy-phenyl)-2-nitro-ethylsulfanyl]-N,N-dimethyl-acetamide; 2-(l- Benzo[l,3]dioxol-5-yl-2-nitro-ethylsulfanyl)-N,N-dimethyl-acetamide; N,N-Dimethyl-2- (2-nitro-l -p-tolyl-ethylsulf anyl)-acetamide; 2-[l-(4-Fluoro-phenyl)-2-nitro- ethylsulfanyl]-N,N-dimethyl-acetamide; N,N-Diethyl-2-(2-nitro-l-phenyl-ethylsulfanyl)- acetamide; N,N-Diethyl-2-[l-(4-methoxy-phenyl)-2-nitro-ethylsulfanyl]-acetamide; 2-(l- Benzo[l,3]dioxol-5-yl-2-nitro-ethylsulfanyl)-N,N-diethyl-acetamide; N,N-Diethyl-2-(2- nitro-l-p-tolyl-ethylsulfanyl)-acetamide; N,N-Diethyl-2-[l-(4-fluoro-phenyl)-2-nitro- ethylsulfanyl]-acetamide; [2-Nitro-l-(2-nitro-ethylsulfanyl)-ethyl]-benzene; 1-Methoxy- 4-[2-nitro-l-(2-nitro-ethylsulfanyl)-ethyl]-benzene; 5-[2-Nitro-l-(2-nitro-ethylsulfanyl)- ethyl] -benzo [ 1 , 3] dioxole ; 1 -Methyl-4- [2-nitro- 1 -(2-nitro-ethylsulf anyl)-ethyl] -benzene; l-Fluoro-4-[2-nitro-l-(2-nitro-ethylsulfanyl)-ethyl]-benzene; O-Ethyl-N-(2-nitro-l- phenyl-ethyl)-hydroxylamine; O-Ethyl-N-[l-(4-methoxy-phenyl)-2-nitro-ethyl]- hydroxylamine; N-(l-Benzo[l,3]dioxol-5-yl-2-nitro-ethyl)-O-ethyl-hydroxylamine; O- Ethyl-N-(2-nitro-l-p-tolyl-ethyl)-hydroxylamine; O-Ethyl-N-[l-(4-fluoro-phenyl)-2- nitro-ethyl]-hydroxylamine; [N-(2-Nitro-l-phenyl-ethyl)aminooxy] -acetic acid; {N-[l-(4- Methoxy-phenyl)-2-nitro-ethyl] aminooxy} -acetic acid; [N-(l-Benzo[l,3]dioxol-5-yl-2- nitro-ethyl) aminooxy] -acetic acid; [N-(2-Nitro-l-p-tolyl-ethyl)aminooxy]-acetic acid; {N-[l-(4-Fluoro-phenyl)-2-nitro-ethyl] aminooxy} -acetic acid; [l-(4-Chloro-phenyl)-2- cyano-ethylsulfanyl]-acetic acid methyl ester; [N-(2-Nitro-l-phenyl-ethyl)aminooxy]- acetic acid methyl ester; {N-[l-(4-Methoxy-phenyl)-2-nitro-ethyl]aminooxy}-acetic acid methyl ester; [N-(l-Benzo[l,3]dioxol-5-yl-2-nitro-ethyl)aminooxy]-acetic acid methyl ester; [N-(2-Nitro-l-p-tolyl-ethyl)aminooxy]-acetic acid methyl ester; {N-[l-(4-Fluoro- phenyl)-2-nitro-ethyl] aminooxy} -acetic acid methyl ester; [2-Cyano-l-(4-methoxy- phenyl)-ethylsulfanyl]-acetic acid methyl ester; [2-Cyano- 1 -(3, 4-dimethoxy-phenyl)- ethylsulfanyl]-acetic acid methyl ester; (2-Cyano- 1 -phenyl-ethylsulf anyl)- acetic acid methyl ester; N'-(2-Nitro-l-ρhenyl-ethyl)-hydrazinecarboxylic acid ethyl ester; N'-[l-(4-

Fluoro-phenyl)-2-nitro-ethyl]-hydrazinecarboxylic acid ethyl ester; N'-(2-Nitro-l-p-tolyl- ethyl)-hydrazinecarboxylic acid ethyl ester; N'-(l-Benzo[l,3]dioxol-5-yl-2-nitro-ethyl)- hydrazinecarboxylic acid ethyl ester; N'-[l-(4-Methoxy-phenyl)-2-nitro-ethyl]- hydrazinecarboxylic acid ethyl ester; 2-[l-(4-Bromo-thiophen-2-yl)-2-nitro- ethylsulf anyl] -propionic acid; {N-[l-(4-Bromo-thiophen-2-yl)-2-nitro-ethyl]aminooxy}- acetic acid; 2-[l-(4-Bromo-thiophen-2-yl)-2-nitro-ethylsulfanyl]-N,N-diethyl-acetamide;

4-Bromo-2- [2-nitro- 1 -(2-nitro-ethylsulf anyl)-ethyl] -thiophene ; 2- [ 1 -(4-Bromo-thiophen-

24. The method as claimed in claim 23, wherein the compound of formula (I) is: : 2-(2- Nitro-1 -phenyl-ethylsulf anyl)-propionic acid; 2-(l-Benzo[l,3]dioxol-5-yl-2-nitro- ethylsulfanyl)-propionic acid; 2-(2-Nitro-l -p-tolyl-ethylsulf anyl)-propionic acid; 2-(2- Nitro-1 -phenyl-ethylsulf anyl)-propionic acid ethyl ester; 2-[l-(4-Methoxy-phenyl)-2- nitro-ethylsulfanyl] -propionic acid ethyl ester; 2-(l-Benzo[l,3]dioxol-5-yl-2-nitro- ethylsulfanyl)-propionic acid ethyl ester; 2-(2-Nitro-l-p-tolyl-ethylsulfanyl)-propionic acid ethyl ester; (l-Benzo[l,3]dioxol-5-yl-2-nitro-ethylsulfanyl)-acetonitrile; (2-Nitro-l- p-tolyl-ethylsulfanyl)-acetonitrile; 2-[l-(4-Methoxy-phenyl)-2-nitro-ethylsulfanyl]-N,N- dimethyl-acetamide; 2-(l-Benzo[l,3]dioxol-5-yl-2-nitro-ethylsulfanyl)-N,N-dimethyl- acetamide; N,N-Dimethyl-2-(2-nitro-l-p-tolyl-ethylsulfanyl)-acetamide; N,N-Diethyl-2- (2-nitro-l-phenyl-ethylsulfanyl)-acetamide; N,N-Diethyl-2-[l-(4-methoxy-phenyl)-2- nitro-ethylsulfanyl]-acetamide; N,N-Diethyl-2-(2-nitro- 1 -p-tolyl-ethylsulfanyl)- acetamid; [2-Nitro-l-(2-nitro-ethylsulfanyl)-ethyl]-benzene; l-Methoxy-4-[2-nitro-l-(2- nitro-ethylsulfanyl)-ethyl]-benzene; 5-[2-Nitro-l-(2-nitro-ethylsulfanyl)-ethyl]- benzo[l,3]dioxole; {N-[l-(4-Methoxy-phenyl)-2-nitro-ethyl]aminooxy}-acetic acid; [N- (l-Benzo[l,3]dioxol-5-yl-2-nitro-ethyl)aminooxy]-acetic acid; {N-[l-(4-Fluoro-phenyl)-

2-nitro-ethyl]aminooxy}-acetic acid; [N-(l-Benzo[l,3]dioxol-5-yl-2-nitro- ethyl)aminooxy] -acetic acid methyl ester; 2-[l-(4-Bromo-thiophen-2-yl)-2-nitro- ethylsulfanyl]-propionic acid; or 2-[l-(4-Bromo-thiophen-2-yl)-2-nitro-ethylsulfanyl]-

N,N-diethyl-acetamide.

25. The method as claimed in claim 24, wherein the compound of formula (I) is: 2-(2-Nitro- l-phenyl-ethylsulfanyl)-propionic acid; 2-[l-(4-Methoxy-phenyl)-2-nitro-ethylsulfanyl]- N,N-dimethyl-acetamide; N,N-Dimethyl-2-(2-nitro-l-p-tolyl-ethylsulfanyl)-acetamide; N,N-Diethyl-2-(2-nitro-l-p-tolyl-ethylsulfanyl)-acetamide; [2-Nitro- 1 -(2-nitro- ethylsulf anyl)-ethyl] -benzene; l-Methoxy-4-[2-nitro-l-(2-nitro-ethylsulfanyl)-ethyl]- benzene; 5-[2-Nitro-l-(2-nitro-ethylsulfanyl)-ethyl]-benzo[l,3]dioxole; or [N-(l- Benzo[l ,3]dioxol-5-yl-2-nitro-ethyl)aminooxy]-acetic acid.

26. The method as claimed in any of claims 22 to 25, wherein the compound of formula (I) is applied at a rate of about 50 g per hectare to about 500 g per hectare.