PL82931B1 - Triazol-3-yl(thio)phosphoric (and phosphonic)acid esters - - useful as insecticides, acaricides, fungicides, etc[CH549944A] - Google Patents

Abstract

Title cpds. of formula (I): (where R1 and R4 are H, alkyl, opt. substd. phenyl or cycloalkyl; R2 is COOR, CONR4R5 or CN; R3 is alkyl, alkoxy or phenyl; R5 is H or alkyl; X is O or S) may be prepd. by reacting the corresp. 3-hydroxytriazole with Hal-P(X)(R3)OR4 (Hal = halogen) in the presence of acid binider. Cpds. (I) are insecticides, acaricides, nematocides, fungicides, bactericides, viricides, selective herbicides, molluscicides and anthelmintics. [CH549944A]

Description

Pesticide The subject of the invention is a pesticide which contains as active substance 0.1-95% of a compound of the general formula I, in which R 1 represents a hydrogen atom, an alkyl, alkenyl, alkynyl, phenyl or cycloalkyl radical, Ra represents the groups —COORi, —CONCRj) (R4) or —C = N, R3 represents an alkyl radical and X represents an oxygen or sulfur atom, and 5-99.1% of suitable carriers and / or other additives. Alkyl radicals denoted by the symbols Rlf, R3 and R4 are suitable, optionally substituted, straight or branched chain radicals having 1-18, preferably 1-4 carbon atoms, such as, for example, methyl, trifluoromethyl, ethyl, cyanoethyl, propyl, iso ¬ propyl and n-, i-, II-order- or III-butyl-order. Cycloalkyl radicals marked with the symbol Rx are suitable radicals with 3-7, especially 5 or 6-membered rings. an occurring phenyl radical may or may not be substituted. Alkyl and phenyl radicals they may contain first or second kind substituents, electron donating substituents, i.e. substituents which increase the basicity of a compound, such as, for example, halogen atoms, such as fluorine, chlorine, bromine or iodine, branched chain, alkoxy groups are defined as substituents of the first type. and alkylthio optionally having 1-4 carbon atoms, preferably 1-2 carbon atoms in an unbranched chain, lower alkoxyalkyl and alkyl groups as defined above, I-, II-, T1-order amino groups, with lower alkyl and alkanol groups as well as hydroxyl and mercaptan groups mentioned as being particularly preferred. Phenyl residues can also contain alkyl radicals? and mono- or dihaloalkyl groups. The second type of substituents are electron-transferring substituents, such as, for example, nitro and cyano, trihaloalkyl groups, especially fluorine or chlorine as halogen, lower alkylsulfinyl alkylsulfonyl groups having an optionally branched alkyl radical containing 1-4 of carbon atoms, and preferably of an unbranched 1-2 carbon chain, sulfamyl and sulfamide groups having one or two substituents in the amino group, such as, in particular, the lower alkyl radicals listed above. Compounds of formula I are especially valuable. Formula 2, where R5 is an alkyl radical with 1-4 carbon atoms, a phenyl or a chlorophenyl radical, R6 is a group of the formulas —COOCH3, —COOC2H5, —CONH2, —CONHCHs or —CON (CH3) 2, R7 is a methyl, ethyl, methoxy or ethoxy radical, R8 is a methyl or ethyl, n-propyl radical and X30 is oxygen or sulfur. 82 93 182 931 3 Compounds of general formula I, in which R1, R2, R3, R4 and X have the above meanings, can be obtained by reacting a compound of formula 3 with a compound of formula IV in which formulas Ru Ra , R3, R4 and X are as defined above, and Hal is a halogen atom, in particular chlorine or bromine, in an acid binding agent environment, or by reacting a salt of the above-mentioned compound of formula III with a compound of formula IV. The hydroxytriazole salts of formula III are suitable for monovalent metals, in particular alkali metals. The acid binders are, for example, tertiary amines, such as triethylamine, dimethylaniline, pyridine, pyridine bases, inorganic bases, such as alkali metal and alkaline earth metal hydroxide and carbonates, such as especially sodium carbonate and potassium carbonate. is carried out in particular in a solvent or diluent which is inert to the reactants, such as aromatic hydrocarbons, for example benzene, toluene, gasoline, chlorobenzene, polychlorobenzenes, bromobenzene, chlorinated alkanes with 1 to 3 carbon atoms, ethers, such as dioxane, tetrahydrofuran, esters, such as acetic acid ethyl ester, ketones, such as methyl ketone, diethyl ketone. The compounds of formula III are new compounds which can be prepared by known methods, for example by reacting a substituted semicarbazide with an orthoester carboxylic acid of the general formula 5, in which R and R 'represent alkyl radicals. Corresponding acid amides and the corresponding non-nitriles. According to the above reaction, the compounds of formula III can be prepared having the melting points listed in Table I. Table I Compound of formula 6 7 8 9 1 10 11 12 I mp ° C 208-210 219-221 240—243 182—185 207—209 210—215 192—193 | The compounds of formula I, which are active ingredients of the agent according to the invention, are characterized by a high biological activity against a wide variety of plant and animal pests and can be used, for example, as substances for combating bacteria, viruses and as selective weed and antimicrobial agents. hello and against worms. The compounds of formula I show, in particular, insecticidal and acaricidal activity against all developmental forms of insects as well as mites, such as, for example, eggs, larvae, pupae, and mature individuals, such as, for example, from the family of Teltigonidae, Gryllidae. , 15 20 25 30 40 50 65 Gryllotalpidae, Blattidae, Peduvidae, Phyrrohocoriae, Gimicidae, Delphacidae, Aphididae, Diaspididae, Pseudococcidae, Scarabaeidae, Dermastidae, Coccinellidae, Tenebrionidae, Chrysomelidae, Chrysomelidae, Chrysidae, Chrysidae, Chrysidae, Pyralidae, Culcidae, Tipulidae, Stomoxydae, Trypetidae, Muscidae, Calliphoridae and Pulicidae, as well as mites from the family Ixodidae, Argasidae, Tetranyidae and Dermanyssidae. The scope of action of the agent according to the invention may significantly extend the condition of the insecticide by adding other insecticides. or acaricides, thus obtaining a pesticide suitable for the given conditions. As substances enabling the extension of the activity range of the active substances According to the invention, for example: 1) organophosphorus compounds, 2) nitrophenols and their derivatives, 3) various organic substances, 4) formamidines, 5) urea derivatives, 6) carbamates and 7) chlorinated hydrocarbons, such as: 1) di-0,0-diethylphosphoric acid anhydride (TEEP) dimethyl / 2,2,2-trichloro-1-hydroxyethyl / phosphonate (TRICHLORFON) 1,2-dibromo-2,2, - dichloroethyldimethylphosphonate ( NALED) 2,2 - dichlorovinyl dimethylphosphonate (DI- CHLORPHOS) 2 - methoxycarbamyl - 1 - methylvinyl dimethyl phosphonate (MEVINPHOS) dimethyl - 1 - methyl - 2 - / methylcarbamoyl / - vinnylphosphonate / eisoxyHOS - MONOCROTOPylumeth N, N - dimethyl - cis - crotonamide (DICROTOPHOS) 2 - chloro - 2 - diethylcarbamoyl - 1 - methylvinyl dimethylphosphonate (PHOSPHAMIDON) 0,0-diethyl-O / or S / -2- / ethylthio / -ethylthiophosphate (DEM ) S - ethylthioethyl - 0.0 - dimethyl - dithiophosphonate (THIOMETONE) 0.0 - diethyl - S - ethyl mercaptomethyl de-thiophosphonate (PHORATE) 0.0 - diethyl - S - 2 - / ethylthio / ethyl - dithiophosphate (DISULFOTON) 0.0 - dimethyl - S - 2 - / ethylsulfinyl / - ethylthiophosphate (OXYDEMETONMETHYL) 0.0 - dimethyl - S - (1,2 - dicarboethoxyethyl) - dithiophosphate (MALATHION) 0,0,0,0 - tetraethyl - S, S '- methylene - di - thio - phosphate (ETHION) 0-ethyl S, S - dipropyl dithiophosphate 0.0 - dimethyl - S - / N - methyl - N - formylcarbamoylmethyl) - dithiophosphate (FORMOTHION) 0.0 - dimethyl - S - / N - methylcarbamoylmethyl / - dithiophosphate (DIMETHOAT) 0.0-dimethyl Op-Nitrophenylthiophosphate (PARA-THION-METHYL) 0.0-Diethyl-Op-Nitrophenylthiophosphate (PARA-THION) O-ethyl-O-p-nitrophenyl) -ethylthiophosphonate (EPN) 82931 6 i, 0-dimethyl-O- / 4-nitro-m-tolyl / -thiophosphate (PE- 1HTROTHION) 0.0 - dimethyl - 0.2,4-5-trichlorophenylthiophosphate 0 - ethyl - -0,2,4,5 - trichlorophenylethylthiophosphonate (TRICHLORONAT) 0.0 - dimethyl - 0.2.5 - dichloro - 4 - bromophenes - lotiophosphate (BROMOPHOS) 0.0 - dimet yl - 0 - / 2.5 - dichloro - 4 - iodophenyl / - thiophosphate (IODOFENPHOS) 4 - III - butyl-2-chlorophenyl-N-methyl-O-methyl phosphoramidate (CRUFOMAT) 0.0 - dimethyl-O- / 3-methyl-4-methylmercaptophenyl / -thiophosphate (FENTHION) isopropylamino - 0 - ethyl - 0 - / 4 - methyl mercapto -3-methylphenyl / -phosphate 0.0 - diethyl - 0 - p - (methylsulfinyl) -phenyl-thiophosphate (FENSULFOTHION) 0 - p - (dimethylsulfamido) - phenyl - 0.0 - dimethylthiophosphate (FAMPHUR) 0.0.0 ', 0' - tetramethyl - 0.0 '- thiodwo - p - phenylenothiophosphate O-ethyl-S-phenyl-ethyldithiophosphonate 0.0 - dimethyl - 0 - la - methylbenzyl - 3 - hydroxycrotonyl 2 - chloro - 1 - / 2,4 - dichlorophenyl / vinyl phosphate - -diethylphosphate (CHLORFENYINPHOS) 2 - chloro - 1 - (2,4,5 - trichlorophenyl) - vinyl - dimethyl phosphate 0 - [2 - chloro - 1 - / 2,5 - dichlorophenyl] - vinyl - -0.0 - phenylglyoxolonitriloxime dimethylthiophosphate - 0.0 - diethylthiophosphate (PHOXIM) 0.0 - diethyl - 0 - / 3 - ch loro - 4 - methyl - 2 - keto - -2-H-1-benzopyrano-7-yl) -thiophosphate (COUMA- PHOS 2,3 - p - dioxandithiol - S, S - di - / 0.0 - diethyl- dithiophosphate) (DIOXATHION) 5 - [(6 - chloro - 2 - keto - 3 - benzoxazolinyl) - methyl] 0,0-diethyldithiophosphate (PHOSALON) 2- (diethoxyphosphinylimino) -1,3-dithiolane 0,0 - dimethyl - S - [2-methoxy-1,3,4-thiadiazole -5- (4H) -nyl- (4'-methyl] -dithiophosphate 0.0 - dimethyl-S-phthalimidomethyl dithiophosphate (IMIDAN) 0.0 - diethyl - 0 - (3,5,6 - trichloro - 2 - pyridyl) / 0.0-diethyl-0-2-pyrazinethiophosphate thiophosphate (THIONA-ZIN) 0.0 - diethyl - 0 - / 2 - isopropyl - 4 - methyl - 6 - pyrimidyl / thiophosphate (DIAZINON) 0.0-diethyl-O- (2-quinoxalyl) -thiophosphate 0.0 - dimethyl - S - / 4 - keto - 1,2,3 - benzotriazine - -3 / 4H (- yl - methyl) - dithiophosphate (AZINPHOS- METHYL) 0.0 - diethyl - S - (4 - keto - 1,2,3 - benzotriazine - -3 / 4H) - yl - methyl) - dithiophosphate (AZINPHSA- ETHYL) S - [/ 4.6 - diamino - s - triazine - 2 - ylom ethyl] - -0.0-dimethyldithiophosphate (MENAZON) 0.0 - dimethyl - 0 - / 3 - chloro - 4 - nitrophenyl / - -thiophosphate (CHLORTHION) 0.0-dimethyl-0- / or s / -2- / ethylthioethyl / -thiophosphate (DEMETON-S-METHYL) chloride 2- (0,0-dimethylphosphorythiomethyl) -5-metho- 3,4 - dichlorobenzyl - triphenyloxypyrone - 4 phosphonium 0.0 - diethyl - S - / 2, 5 - dichlorophenylthiomethyl / -dithiophosphate (PHENKAPTON) 5 0.0 - diethyl - 0 - (4 - methylcoumarinyl - 7) - thiophosphate (POTASANE) 5 - amino - di - (dimethylamido) - phosphinyl - 3 - phenyl -1,2,4-triazole (TRIAMIPHOS) N - methyl - 5 - / 0.0 - dimethylthiolphosphoryl) - 3 - io-triavalerylamide (VAMIDOTHION) 0.0 - diethyl - 0 - [2 - dimethylamino - 4 - methyl- lopyrimidyl- (6)] thiophosphate (DIOCTYL) 0.0 - dimethyl - S - (methylcarbamoylmethyl) - -thiophosphate (OMETHOAT) 15 O-ethyl-O- (8-quinQlinyl) -phenylthiophosphonate (OXINO- THIOPHOS) O-methyl- HOS S-methyl-amidothiophosphate (MONITOR) 0 - methyl - 0 - / 2,5 - dichloro - 4-bromophenyl / - benzothiophosphony n (PHOSYEL) 20 0,0,0,0-tetrapropyl dithiopyrophosphate 3 - (dimethoxyphosphinyloxy) - N - methyl - N-methoxy-cis-crotunamide 0.0 - dimethyl - S - / N - ethylcarbamoylmethyl / - dithiophosphate (ETHOT -METHYL) 25 0.0 - diethyl - S - / N - isopropylcarbamoylmethyl / -dithiophosphate (PROTHOAT) S - N - / 1 - cyano - 1 - methylethyl / - carmamoylmethyl diethylthiophosphate (CYANTHOAT) S- / 2-acetamidoethyl / -0.0-dimethyldithiophosphate 30 hexamethylphosphoric acid triamide (HEMPA) 0.0 - dimethyl - 0 - / 2 - chloro-4 - nitrophenyl / - -thiophosphate (DICAPTHION) 0.0-dimethyl-Op-cyanophenyl thiophosphate (CYA- NOX ) 35 O-ethyl-O-p-cyanophenylthiophosphonate 0.0-diethyl-0-2,4-dichlorophenylthiophosphate (DI- CHLORFENTHION) 0.2,4 - dichlorophenyl - O - methylisopropylamidothiophosphate 40 0.0 - diethyl - 0 - 2,5 - dichloro - 4 - bromophenolylphosphate (BROMOPHOS-AETHYL) dimethyl p- (methylthio) phenylphosphate 0.0-dimethyl-Op-sulfamidophenylthiophosphate 0 - [p - / p - chlorophenyl / azaphenes Io] - 0.0 - dimethyl-50-lotiphosphate (ATOTHOAT) O-ethyl-S-4-chlorophenylethyldithiophosphonate O-isobutyl-Sp-chlorophenyl ethyldithiophosphonate 0.0-dimethyl-Srp-chlorophenylthiophosphate 0.0-dimethyl - S - / p - chlorophenylthiomethyl / - 50-dithiophosphate 0.0 - diethyl-p - chlorophenyl mercaptomethyl-dithiophosphate (CARBOPHENOTHION) 0.0-diethyl-Sp-chlorophenylthiomethyl-thiophosphate 0.0 - dimethyl-S - / carboethoxyphenylmethyl diphosphate PHENTHOAT) 0.0 - diethyl - S - / carbofluoroethoxyphenylmethyl / -dithiophosphate 0.0 - dimethyl - S - / carbisopropoxyphenylmethyl / dithiophosphate 60 0.0 - diethyl - 7 - hydroxy - 3,4 - tetramethylene coumarinyl -thiophosphate (COUMITHOAT) 2 - methoxy - 4 - H - 1,3,2 - benzodioxaphosphite--2-sulphide 0.0 - diethyl - 0 - / 5 - phenyl - 3 - isoxazolyl / - 65 - thiophosphate 82 931 7 2 - (diethoxyphosphinylimino) - 4-methyl-L, 3 - tris- (2-methyl-1-aziridinyl) -phosphine oxide (METE-PA) S- (2-chloro-1-phthalylimido-diethyl) N-hydroxynaphtholimido-diethylphosphate dimethyl-3,5,6-trichloro-2-pyridylphosphate 0,0 - dimethyl - 0 - / 3,5,6 - trichloro - 2 - pyridyl / - S - 2 - thiophosphate (ethylsulfonyl) / - ethyl - dimethylthiophosphate (DIQXYDEMETON-S-METHYL) diethyl - S - 2 - (ethylsulfinyl) - ethyl - dithiophosphate (OXYDISULFOTON) di-0,0-diethylthiophosphoric anhydride (SUL.FOTEP) 3 - di- (carbomethoxy) - 1 - propen-2-yl phosphate dimethyl - (2,2,2-trichloro-1-butylyloxyethyl) phosphonate (BUTONAT) 0.0 - dimethyl - 0 - / 2, 2 - dichloro - 1 - zethoxyvinyl / di- (dimethylamido) phosphate / -fluorophosphate (DIMEFOX) dimethyl 3,4-dichlorobenzyltriphenylphosphonium chloride - N - methoxymethylcarbamoylmethyl-di-difutiophosphate - 0 - / MOCARBARBAM 2,2 - Dichloro - 1 - ChloroethoxyvinylZ-Phosphate 0.0 - Dimethyl - 0 - / 2.2 - Dichloro - 1 - Chloroethoxyvinyl / O-ethyl-S, S-diphenyldithiophosphate O-ethyl-S- benzyl-phenyldithiophosphony ian 0.0-diethyl-S-benzylthiolphosphate 0.0 - dimethyl-S - (4 - chlorophenylthiomethyl) - -dithiophosphate (METHYLCARBOPHENOTHION) 0.0-dimethyl-S- / ethylthiomethyl / -dithiophosphate diisopropylthiomethyl dimethyl - S - (morpholinylcarbamoylmethyl) -dithiophosphate (MORPHOTONIN) dimethylamidophenylphosphate 0.0-dimethyl-S- (benzenesulfonyl / dithiophosphate), 0.0-dimethyl- (SiO) -ethylsulfinylethyl-O, O, 4-nitrophephosphosphate - di / thiophosphinyl / disulfide 2 - methoxy - 4H - 1 - 1,3,2 - benzodioxaphosphite-2-oxide octamethylpyphosphoramidate (SCHRADAN) di / dimethoxithiophosphinylsulfide / -phenylmethane N, N, N ', N'-tetramethyldiphoramidate - MEFOX) O-phenyl-O-p-nitrophenylmethanothiophosphonate (COLEP) 0 - methyl - O - / 2 - chloro - 4 - order - butylphenyl / -N-methylamidothiophosphate (NARLENE) O-ethyl-O- (2,4-dichlorophenyl) -phenylthiophosphonate 0,0 - diethyl - 0 - / 4 - methyl mercapto - 3,5 - dimethylphenyl Z-thiophosphate 4 , 4 '- di - (0.0 - dimethylthiophosphoryloxy) - diphenyldisulfide 0.0 - di - l (and - chloroethyl) - 0 - (3 - chloro - 4 - methyl coumarinyl-7) -phosphate S - (1-phthalylimidoethyl) -0,0-diethyldithiophosphate 0.0 - dimethyl - 0 - / 2 - carboisopropoxyphenyl) - 5T amidothiophosphate / 0.0 - dimethylphosphoryl / - 6 - chloro - bicyclo / 3.2.0 / - heptadiene- (1,5 / 8 0 - methyl - 0 - / 2 - and - propoxycarbonyl - 1 - methylvinyl) -ethylamido-thiophosphate nitrophenols and their derivatives as: Na 4,6-dinitro-6-methylphenol salt (dinitrocresol ) 5 dinitrobutylphenol salt (2,2 ', 2), - triethanolamine 2-cyclohexyl-4,6-dinitrophenol (DINEX) 2- (1-methylheptyl) - 4,6 - dinitrophenyl caotonate (DINOCAP) acid derivatives as: and II - butyl-4,6-dinitrophenyl-3-methyl-butyl (BINAPACRYL) tier-butyl-4,6-dinit rophenylpropionic II - butyl - 4,6 - dinitrophenyl - isopropyl carbon (DINO BUTON) 15 Miscellaneous compounds: Pyrethrin I, Pyrethrin II, allyl - 2 - methyl - 4 - keto - 2 - cyclopentene - 1 - yl-chrysanthemate (Allethrin) 6-chloropiperanyl-chrysanthemate (tarthrin) 2,4-dimethylbenzyl chrysanthemate (dimethrin) 20 2,3,4,5-tetrahydrophthalimidomethylchrysanthemate 4-chlorobenzyl-4-chlorophenyl sulfide (chlorobenside) 6 - methyl - 2 - keto - 1,3 - dithiolo - 4,5 - b / - quinoxaline (aninomethionate) 25 monocarboxylate / l / -3- / 2-furfuryl / -2-methyl-4-ketocyclopent-2-enyl / l / - / cis + trans / chrysanthines (Fu- rethrin) 2-pivaloyl-indan-1,3-dione (Pindone) N - / 4 - chloro - 2 - methylphenyl / - N, N - dimethyl-phosphorformanidine (Chlorafenamidine) 4-chlorobenzyl-4-fluorophenyl sulfide (Fluorobenside) benzimidazole 5,6-dichloro-1-phenoxycarbamyl -2-trifluoromethyl (Phenozaflor) 35 p-chlorobenzenesulfonate p-chlorophenyl (Ovex) p-chlorophenyl benzosulfonate (Fenson) chlo rophenyl-2,4,5-trichlorophenylsulfone (Tetra-diophone) p-chlorophenyl-2,4,5-trichlorophenylsulfide (Tetra-40SUl) p-chlorobenzyl-p-chlorophenylsulfide (Chlorbensi * de) 2-thio-1,3 -dithiol-5,6H-quinoxaline (Thiochinox) prop-2-ynyl- / 4-III-butylphenoxy / -cyclohexyl (Propargyl) sulfite Formamides like: 1-dimethyl-2- / 2 / -methyl -4'-chlorophenyl / -formamidine (CHLORPHENAMIDIN) 1-methyl-2- (2'-methyl-4) -chlorophenyl) -firmamidine 1-methyl-2- (2'-methyl-4) -bromophenyl / - formamidine 50 l-methyl-2- / 2 /, 4) -dimethylphenyl) -formamidine 1 - n - butyl - 1 - methyl - 2 - / 2 '- methyl - 4' - chlorophenyl Z-formamidine 1-methyl-1- / 2'-methyl-4'-chloroanilinomethylene / 2- / 2 '/ - methyl-4 /, - chlorophenyl / -formamidine 55 1 - n - butyl - 2 - / 2' - methyl - 4 '- chlorophenylamine / -pyrrolidine ureas such as: N-2-methyl-4-chlorophenyl-N, N'-dimethylthiourea carbamates, such as 1-naphthyl-N-methylcarbamate 60 (CARBARYL) 2-butinyl-4-chlorophenylcarbamate 4 - dimethylamino - 3, 5 - xylyl o - N - methylcarbamate 4 - dimethylammonium, - 3 - tolyl - 4 - methylcarbamate (AMINOCARB) 82 931 9 10 4 - methylthio - 3,5 - xylyl - N - methylcarbamate (METHIOCARB) 3,4,5 -trimethylphenyl-N-methylcarbamate 2-chlorophenyl-N-methylcarbamate (CPMC) 5 - chloro - 6 - keto - 2 - norbornanecarbonitrile - O- / methylcarbamido / oxime 1 - / dimethylcarbamoyl / - 5 - methyl - 3 - pyrazolyl - N, N - dimethyl carbamate (DIMETILAN) 2,3 - dihydrogen - 2,2 - dimethyl - 7 - benzofuranyl-4-methylcarbamate (CARBOFURAN) 2 - methyl - 2 - methylthiopropionaldehyde - 0 - / methylarmbamoyl) oxime (ALDICARB) 8-quinaldyl-N-methylcarbamate and its salts methyl-2-isopropyl-4 - (methylcarbamoyloxy) carbanilate m- (1-ethylpropyl) phenyl-N-methylcarbamate 3,5-di-III-butyl-N -methylcarbamate m- (1-methylbutyl) phenyl-N-methylcarbamate 2-isopropylphenyl-N-methylcarbamate 2-II-tert-butylphenyl-N-methylcarbamate m-tolyl-N-methylcarbamate 2,3-xylyl-N-methylcarbamate 3-Isopropylphenyl-N-methylcarbamate 3-tert.butylphenyl-N-methylcarbamate 3-II-tert.butylphenyl-N-methylcarbamate 3-isopropyl-5-methylphenyl - N-methylcarbamate (PROMFCARB) 3,5- diisopropylphenyl-N-methylcarbamate 2-chloro-5-isopropylphenyl-N-methylcarbamate 2-chloro-4,5-dimethylphenyl-N-methylcarbamate 2 - (1,3-dioxalate-2-yl (- phenyl - N - methyl carbamate) (DIOXACARB) 2 - (4,5-dimethyl-1,3-dioxalate-2-yl) -phenyl-N-methylcarbamate 2 - (1,3-dioxalate-2-yl (-phenyl-N, N - 2 - (1,3 - 2 - yl) - N, N - dimethylcarbamate 2 - (1,3 - dithiolane - 2 - yl) phenyl - N, N - dimethyl carbamate 2 - isopropoxyphenyl dimethyl carbamate -N-methylcarbamate (APRO- CARB) 2- (2-propionyloxy / phenyl-N-methylcarbamate 3- (2-propionyloxy) phenyl-N-methylcarbamate 2-dimethylaminophenyl N-methylcarbamate 2-diallylaminophenyl N-methylcarbamate 4-diallylamino -3,5-xylyl-N-methyl carbamate (ALLYXICA RB) 4-benzothienyl-N-methylcarbamate 2,3-dihydrogen-2-methyl-7-benzofuranyl-N-methyl carbamate 3-methyl-1-phenylpyrazole-5-yl-N, N-dimethylcarbamate 1-isopropyl - 3 - methylpyrazole - 5 - yl - N, N - dimethylcarbamate (ISOLAN) 2 - dimethylamino - 5,6 - dimethylpyrimidine -4-yl-N, N-dimethylcarbamate 3 - methyl - 4 - dimethylaminomethyleneiminophenyl carbamate N-methylcarbamate 3 - dimethylaminomethyleneiminophenyl - N - methyl carbamate (FORMETANATE) and its salts 1-methylthioethylimino-N-methylcarbamate (ME-THOMYL) 2-methylcarbamoyloxyimino-1,3-dithiolate 5 - methyl - 2 - methylcarbamoyloxyimino - 1,3 - oxytiolate / 1-methoxy-2-propoxy / phenyl-N-methylcarbamate 2- (1-butin-3-yloxy) phenyl-N-methylcarbamate 5 1 - dimethylcarbamyl - 1 - methylthio - O - methylcarbamylformoxime 1 - / 2 '- cyanoethylthio / - 0 - methylcarbamyl - acetaldoxime 1-methylthio-O-carbamyl-acetaldoxime 0 - / 3 - II - butylphenylthio / - N - phenylthio - N - - 2,5 - dimethyl - 1,3 - dithioland - 2 - (O - methylcarbamyl) -aldoxime methylcarbamate 0-2-diphenyl-N-methylcarbamate 15 2 - (N - methylcarbamyloxyimino) - 3 - chloro-bicyclo [ 2,2,1] -heptane 2 - (N-methylcarbamyl-oxyimino) -bicyclo [2,2,1] -heptane 3-isopropylphenyl-N-methyl-N-chloroacetylcarbamate 3-isopropylphenyl - N-methyl - N - methylthiomethyl carbamate 0 - / 2,2 - dimethyl -4 - chloro - 2,3 - dihydro-7-benzofuranyl-N-methyl carbamate 25 0 - (2,2,4-trimethyl - 2,3) - dihydro - 7 - benzofuranyl-N-methylcarbamate O-naphthyl-N-methyl-N-acetylcarbamate 0-5,6,7,8-tetrahydro-naphthyl-N-methylcarbamate 3 - isopropyl - 4 - methylthiodenyl - N - methylcarbamate 30 3,5-dimethyl-4-methoxyphenyl-4-methylcarbamate 3-methoxyphenyl-N-methylcarbamate 3-allyloxyphenyl-N-methylcarbamate 35 2-propargyloxymethoxy-phenyl-N-methylcarbamate 2-allyloxyphenyl-N-methylcarbamate 4 - methoxycarbonylamino - 3 - isop ropylphenyl -N-methylcarbamate 40 3,5-dimethyl-4-methoxycarbonylaminophenyl-N-methylcarbamate 2 - ^ - methylthiopropylphenyl-N-methylcarbamate 3 - la - methoxymethyl - 2 - propenyl / - phenyl - N - methylcarbamate 2 - chloro - 5 - tertiary butylphenyl - N - methyl carbamate 4 - (methylpropargylamino) - 3,5 - xylyl - N - methyl carbamate 50 4 - (methyl chlorallylamino) - 3,5 - xylyl - N - methyl carbamate 4 - / methyl - § - chlorallylamino / - 3,5 - xylyl - N - methylcarbamate 1 - //? - ethoxycarbonylethyl) - 3 - methyl - 5 - pyrazolyl-N, N-dimethylcarbamate 3 - methyl - 4 - (dimethylamino - methylmercapto-methyleneiminoAphenyLo-N-methylcarbamate 1,3 - di - (carbamylthio) hydrochloride - 2 - / N, N - dimethylamino) propane eo 5,5 - dimethyl hydroresorcinol dimethyl carbamate 2 - [ethyl propargylamino] phenyl - N - methyl carbamate 2 - [methyl propargylamino] phenyl - N - methyl 65 carbamate 4582 931 11 2 - [dipropargylamino] - phenyl - N - methylcarbamate 4 - [dipropargylamino] - 3 - tolyl - N - methylcarbamate 4 - [dipropargylamino] - 3,5 - xylyl - N - methylcarbamate 2 - [allyl - isopropylamino] - phenyl - N - methyl carbamate 3 - [allyl isopropylamino] - phenyl - N - methyl carbamate Chlorinated hydrocarbons such as: γ-hexachlorocyclohexane [GAMMEXANE, LIN¬ DAN, y HCH] 1,2,4 , 5,6,7,8,8-octachloro-3a, 4,7,7a'-tetrahydro-4,7-methylenindane [CHLORDAN] l, 4,5,6,7,8,8-heptachloro- 3ct-4,7,7a-tetrahydro-4,7- methyleneindane [HEPTACHLOR] 1,2,4,3,10,10-hexachloro-1,4,4a, 5,8,8a - hexahydro -endo-4-exo-5,8-dimethanonaphthalene (ALDRIN] 1 , 2,3,4,10,10 -hexachloro - 6,7 - epoxy - 1,4,4a, 5,6,7, 8,8a - octahydro - ekzo - 1,4 - endo - 5,8 - two-meter - nonaphthalene [DIRLDRIN] 1,2,3,4,10,10 - hexachloro - 6,7 - epoxy - 1,4,4a, 5,6,7, 8,8 - octahydro - endo - endo - 5, 8 - dimethylnaphthalene [ENDRIN] The active substances of formula I also show fungicidal properties against phytopathogenic fungi attacking various farmed plants such as cereals, maize, rice, vegetables, ornamental plants, fruit trees, vine, field fruit, etc. With the active ingredient according to the invention, it is possible to inhibit the vegetation or destroy the fungi growing on fruits, flowers, leaves, stems, buds and roots, while also achieving the effect that the parts of plants that grow later are protected against fungal attack. The active substances of formula I are particularly effective against phytopathogenic fungi belonging to the classes, orders or species listed below, such as: Oomycytes, such as: Plasmodiophora, Aphanomyces, Pythium, Phytophthora species (Phytophthora infestans, Phytophthora cactus mopara (Plasmopara viticola), Bremia species (Bremia lactucae), Peronospora species (Peronospora tabacina), Pseudoperonospora (Pseudoperonospora humuli) Zygomycetes, such as Rhizopus-Arten species, Ascomycetes such as Eurotiales, for example : Aspergillus, Penicillium (Penicillium digitatum, Penicillium italicum), Taphrinales, for example species: Taphrina (Taphrina deformans) Erysiphales, for example Erysiphe species (Erysiphe cichoracotheum, Erysiphe graminis, Podosphaera (Sphotha- sphaera) species pannosa), Uncinula species: (Uncinula necator), Helotiales, such as Monilinia species (Monilinia Sclerotinia) fructioola, (Monilinia laxa), Dip species lo-carpon, (Diplocarpon rosae), Pseudopeziza species, Sphaeriales, such as Nectria species (Nectria galligene), Ceratocystis species, Pseudosphaeriales, such as Venturia species (Venturia inaeaualis), Mycosphaerella species, Ophiobolus species (Ophiobolus graminus), Cochliobeanus (Helminthosporium miyabeanus), 12 Cercospora species (Cercospora beticola, Cercospora mussae) Basidiomycetes such as Aphyllophorales, for example Pellicularia species (Pellicularia filamento- 5ra) = (Rhizoctonia sonlani, na Uredinales) ¬ Clade of Puccinia species (Puccinia triticina), Uromyces species (Uromyces phaseoli), Hemileia species (Hemileia vastatrix), Cronartium species (Cronartium ribicola), Phragmidium species (Phragmidium io subcorticium), Gymnóx sporangium species (Fungiycetes = Fungi. example Piricularia species (Piricularia ory- zae) Corinespora species, Thielaviopsis species, Clasterosporium species, Botrytis species (Botrytis cinerea), Cladosporium species , Alternaria species (Alternaria solani), Verticillium species (Verticillium or atrum), Phialophora species, Melanconiales, for example Colletotrichum species ,. Fusarium species (Fusarium oxysporum, Fusarium 20 nivalc), Glocosporium species (Gloeosporium fructigenum), Sphaeropsidales, for example Septoria species (Septoria apicola), Diplodia species (Di- plodia natalenis), Mycelia sterilia, for example Sclerotium species (Sclerotium species Sclerotium rolfsii). The new active compounds of the formula I can also be used in the treatment of seeds, fruits, tubers etc. to protect them against fungal infections, for example of all kinds of root fungi, such as the order of Ustaliaginales, for example Ustilago species (Ustilage avenae). , Tilletia species (Tilletia tritici), Urocystisund Tuburoinia species, Phoma species (Phoma betae). The active ingredients of the formula I can be used together with nematocides, insecticides and bactericides to broaden the range of action. , and agents controlling the growth of bacteria, fungi, nematodes and / or fungicides, such as: dodecylguanidine acetate (DODINE) 40 pentochloronitrobenzene (QUINTOZENE) pentachlorophenol (PCP) 2 - / l - methyl - b-propyl / - 4.6 - dinitrophenyl - -2-methylcrotonate (BINAPACRYL) 2 - (1 - methyl - n - heptyl) - 4,6 - dinitrophenyl 45 crotonate (DINOCAP) 2,6-dichloro-4-nitroaniline (DICHLORAN) 2,3,5,6- tetrachlorobenzoquinone (1.4) [CHLO RANIL] 2,3-dichloronaphthoquinone / 1,4 / [DICHLONE] N- / trichloromethylthio / phthalimide (FOLPET) 50 N - / trichloromethylthio / - cyclohexene - 4 / - 1,2 - -dicarboximide (CAPTAN) N - / l, 1,2,2-tetrachloroethylthio) - cyclohex - 4 - en-1,2-dicarboximide (CAPTAPOL) N - methylsulfonalo - 4 - trichloromethylthio - chloroaniline N '- dichlorofluoromatylthio - N - dimethyl - -N'-phenylsulfamide (DICHLORFLUAMID) O-ethyl-S-benzylphenyldithiophosphate 0.0-diethyl-S-benzylthiolphosphate 6o disodium-ethylene-1,2-di-dithiocarbamate (NA-BAM) zinc-ethylene-1,2-dithiocarbamate (ZINEB) mangano (II) - ethylene - 1,2 - di-dithiocarbamate (MANEB) 65 tetramethylthiuramide sulfide (THIRAM) 82 931 13 1 - oxy - 3 - acetyl - 6 - methyl - cyclohexane - (5) - -dione- ( 2,4) 8-hydroxyquinoline dehydroacetic acid 2 - dimethylamino - 6 - methyl - 5 - n - butyl - -4-hydroxypyrimidine methyl - N - benzoimidazole - 2 - yl - N - / butylcarbamoyl / carbamate (BENOMYL) 2-ethylamino-6-methyl-5-n- butyl-4 - hydroxypyrimine 2,3-dicyano-1,4-dithiaanthraquinone (DITHIANON) 2- (4-thiazolyl) benzimidazole 3,5 - dimethyl tetrahydro - 1,3,5 - thiadiazine - 2 - thion (DAZOMET ) 2,3-dihydro-5-carboxyanilido-6-methyl--1,4-oxathine 5-chlorobenzyl alcohol The active compound of the formula I can, if appropriate, be used together with suitable carriers and / or additives. The usable carriers and additives may be solid or liquid. These are substances normally used in the pesticide formulation technique, such as, for example, natural or regenerated substances, solvents, dispersants, wetting agents, adhesives, thickeners, binders and / or fertilizers. of the formula (I) are used in the form of preparations such as spraying powders, emulsifiable concentrates, granules, suspensions, sprays, solutions or suspensions, prepared according to generally known principles. They can also be used for the preparation of baths for cattle or showers, in which case aqueous solutions are used. The compositions according to the invention are prepared by generally known methods of thoroughly mixing and / or grinding the active ingredient of the formula I together with a suitable carrier, if necessary. the optional addition of dispersants or solvents inert to the active ingredient. The active substances can be converted into the following utilities: permanent dusts, spreading agents, granules, coated granules, impregnated and homogeneous granules, into liquid preparations which can be dispersed in water active substance concentrates, wettable powders, pastes, emulsions and solutions. In order to prepare solid preparations, such as for dusting and spreading, the active substance is mixed with solid carriers such as, for example, kaolin, talcum, clay bolus, loess, chalk, limestone, limestone, active clay, dolomite, diatomaceous earth, lost silicic acid, alkaline earth metal silicates, sodium and potassium aluminosilicates (feldspar and pimple), calcium and magnesium sulphates, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ground plant products such as corn flour, wood bark flour, wood flour, nut lupine flour, cellulose powder, residues from extraction of plant materials, activated carbon, etc. Granules can be easily prepared, for example, by dissolving the active ingredient of the formula I in an organic solvent, applying the obtained solution to a granulated mineral as in Examples include attapulgite, silica, granitized limestone, bentonite and subsequent evaporation of an organic solvent. Granules can also be prepared by mixing the active ingredient of the formula I with polymerizable compounds, such as mixtures of urea and formaldehyde, - amide with formaldehyde, melamine with formadehyde, etc., subjecting these compounds to polymerization under such conditions that the active substance is not inactivated, provided that the gelling process is carried out during the production of the gel. However, it is more advantageous to proceed according to which ready-made, porous polymeric granules, for example urea-formaldehyde, polyacrylonitrile, polyester and other granules, with a defined external surface and a preferred predetermined adsorption / desorption ratio, they are saturated with the active substances, for example solutions of the active substances in a low-boiling solvent, and the solvent is then evaporated off. The granules obtained in this way can be used as so-called Microgranules, with a bulk weight of 300-600 g / l and apply them by means of sprays, with possible dusting of large surfaces from airplanes. Granules can also be prepared by compressing the carrier with the active substance and additives and then grinding These mixtures can be supplemented with additives to stabilize the active substances and / or non-ionic, anionic and cation-active substances which improve the adhesion of the active ingredient to plants and plant parts, adhesion promoters, adhesives and / or better wettability as well as suspending properties. Suitable substances of this type include, for example, mixtures of olein with limestone, cellulose derivatives such as methylcellulose, carnethoxycellulose, hydroxyethanediol ether, mono- and dialkylphenols with 5-15 ethylene oxide groups per molecule and 8-9 carbon atoms. in the alkyl radical, their alkali metal or alkaline earth metal salts, polyethanediol polyether (Carbowachs) polyglycol ethers of aliphatic alcohols with 5-20 ethylene oxide radicals in the molecule and 8-18 carbon atoms in the alcohol part, products condensation of ethylene oxide, propylene oxide, polyvinylpyrrolidone, polyvinyl alcohols, urea formaldehyde condensation products and latex products. Water-dispersible active ingredient concentrates, i.e. wettable powders, pastes and emulsion concentrates are agents which can be diluted with water to any concentration. These preparations contain the active ingredient, the carrier and, if appropriate, additional agents, such as stabilizing active ingredients, surfactants, antifoams and, optionally, solvents. 10 15 20 25 30 35 40 45 50 55 6015 Powders and wettable pastes are prepared by mixing the active ingredient with dispersants and powdered carriers in suitable equipment until the product is homogeneous and then grinding. As carriers, the products mentioned above can be used in the preparation of solid preparations, but in some cases a mixture of different carriers is preferably used. As dispersants, for example, condensation products of sulfonated naphthalene and sulfonated naphthalene derivatives with formaldehyde, sulfonate condensation products can be used. Of naphthalene or naphthalenesulfonated acids with phenol and formaldehyde, as well as alkali metal, ammonium and alkaline earth metal salts with lignosulfonic acid, as well as alkylarylsulfonates, alkali metal and alkaline earth metal salts with dibutylnaphthalenesulfonic acid, alkoxyl sulfonates - fatty acids, such as salts of hexadecanols, heptadecanols, octadecanols with substituted sulfate groups, and salts of glycol ethers of aliphatic alcohols with substituted sulfate groups, sodium oleyl methyl tauride, tertiary diethandiols, chloride Dialkyl dulauryl ammonium and salts of alkali metals, alkaline earth metals and alkaline earth metals with fatty acids. For example, silicone oils can be used as antifoams. The active substances are mixed with the above-mentioned additives, and then ground and sieved daily protect the ingredients so that the grain size of the wettable powder does not exceed 0.02-0.04 mm, and that of the solid ingredients of the paste does not exceed 0.03 mm. The dispersants discussed above, as well as organic solvents and water, are used to prepare emulsion concentrates and pastes. Suitable solvents are, for example, alcohols, benzene, xylenes, toluene, methyl sulphoxide, and petroleum fractions with a boiling point of 120 ° -350 ° C. The solvents used should be practically odorless and non-toxic to the plants as well as inert to the active ingredient. The composition according to the invention may also be in the form of a rtf-form, prepared, for example, by dissolving one or more active ingredients in a suitable organic solvent or solvent mixture or in water. Suitable organic solvents are aliphatic and aromatic hydrocarbons, their chlorinated derivatives, alkyl naphthalenes, mineral oils or mixtures of these substances. 55 The content of the active substance in the above-mentioned preparations ranges from 0.1 to 95%, but in the case of distribution of these preparations by airplanes or other devices, preparations containing up to 99.5% of the substances can be used. active ingredients, and even pure active ingredients. Preparations containing the active ingredient of the formula 1 can be prepared, for example, from the following ingredients: for the preparation of preparations for dust containing 2 to 5% of the active ingredient For example with 2%, the following are used: 2 parts active ingredient, 1 part fine silica, 97 parts talcum powder, and 5% formulation with 5 parts substance and 95 parts talcum. The active substances are mixed with the carrier and ground. A granule containing 5% of the active ingredient is prepared from 5 parts of the active ingredient 0.25 parts of epichlorohydrin 0.25 "polyether cetyl glycol 3.50" polyethandiol 91.00 "kaolin, grain size 0.3-0.8 mm. The active ingredients are mixed It is mixed with epichlorohydrin and then dissolved in 6 parts of acetone, and then polyethylene glycol and polyglycol cetyl ether are added. Kaolin is sprayed with the solution obtained, and then the acetone is evaporated under reduced pressure. wettable powders the following ingredients are used for the powder: 40%: 40.0 parts of the active ingredient 5.0 "sodium lignin sulfonic acid 1.0 parts sodium dibutylnaphthalenesulfonic acid 54.0 parts silica 25%: 25.0 parts of the active substance 4.5 "calcium salt of lignin sulfonic acid 1.9 parts of a mixture of equal parts by weight of champagne chalk and hydroxyethyl cellulose 1.5 parts of sodium dibutylnaphthalene sulphonic acid 19.5 parts of silica 19.5" champagne chalk 28.1 Kaolin 25%: 25.0 parts of the active ingredient 2.5 isooctylphenoxy polyoxyethylene ethanol 1.7 parts of a mixture of equal parts champagne chalk and hydroxyethyl cellulose 8.3 parts sodium aluminosilicate 16.5 parts earth of diatomaceous 46.0% kaolin 10%: 10.0 parts of the active ingredient 3.0 parts of a mixture of sodium salts, sulfates of saturated aliphatic alcohols 5.0 parts of naphthalenesulfonic acid condensate with formaldehyde 82 0 parts kaolin. The active substances are thoroughly mixed in suitable mixers and ground in suitable mills and rollers. Wettable powders are obtained which can be diluted with water to the desired concentration. Emulsion concentrates. The following ingredients are used to prepare an emulsion concentrate containing 10% or 25% of the active ingredient: 10%: 10.0 parts of active ingredient 82 931 17 18 3.4 "esterified vegetable oil, 13.4 parts of an emulsifier composed of a glycol polyether of an aliphatic alcohol. and calcium salt of alkylaryl sulfonate 40.0 parts dimethylformamide 43.2 parts xylene 25 2.5 parts cyclically etherified vegetable oil 10.0 parts mixture of alkylaryl sulphonate and glycol polyether glycol 5.0 parts dimethylformamide 57.5 xylene From the above after dilution with water, emulsions of any concentration of active substance can be obtained. Dust preparations are prepared from the following components: 5%: 5.0 parts of active substance 1.0 "epichlorohydrin 94.0" gasoline with boiling point 160-190 ° C. The method according to the invention is illustrated by the following examples illustrating the preparation of an active substance generally as well as the results of biological tests. Example I. a) 17.9 g of ethyl ester of 1-phenyl-3-hydroxy-1,2,4-triazole-5-carboxylic acid and 10.6 g of potassium carbonate in 500 ml of methyl ethyl ketone are heated under reflux and, after the elimination of CO 2 is complete, the reaction mixture is cooled to ambient temperature and a solution of 14.5 g of diethyl phosphoric acid chloride in 100 ml of methyl ethyl ketone is introduced with stirring. The mixture is then refluxed for 1 hour and then stirred for 12 hours at ambient temperature. The solution is filtered, the filtrate is evaporated under reduced pressure and the remaining precipitate is dissolved in methanol, then the mixture of acetone and solid CO 2 is cooled to give O- [phenyl-5-ethoxycarbonyl-1,2,4-triazolyl- (3)] - 0.0 - diethyl-thiophosphate, m.p. 54-55 ° C. Active substance No. 1) b) 17.8 g of ethyl ester of 1-phenyl-3-hydroxy-1,2 , 4-triazole-5-carboxylic acid with 10 g of potassium carbonate, in 200 ml of methyl ethyl ketone, is heated under reflux for 1 hour, and after cooling, a solution of 15 g of 0-ethyl-ethylthiophosphonic acid chloride in 50 ml of methyl ethyl ketone is added dropwise to the mixture. The reaction mixture is heated for 30 minutes under reflux, then stirred for 12 hours at ambient temperature and filtered. The solvent is distilled off and the residue is chromatographed on silica gel, eluting with acetone. The amount of gel used is 20 times (0.05-0.2 mm) of the substance to be purified. There is obtained 0- [1-phenyl-5-ethoxycarbonyl-1,2,4-triazolyl (3)] - O-ethylc-ethylthiophosphonate with n201.5394, designated as active substance D on No. 2 According to the above-mentioned method, it is possible to obtain the further compounds listed in Table I. Table I 10 15 20 25 30 40 45 50 55 65 No. 3 - 4 5 6 7 8 9 10 11 12 13 14 15 16 0- [l -phenyl-5-N-methylcarbamoyl-1,2,4-triazolyl- (3)] - 0,0-diethyl-thiophosphate 0- [1-phenyl-5-carbamoyl-1,2, 4-triazolyl-dimethyl-thiophosphate 0- [1-phenyl-5-N-methylcarbamoyl-1,2,4-triazolyl- (3)] - O-ethyl-ethylthiophosphonate 0- [1- phenyl-5-N, N-dimethylcarbamoyl-1,2,4-triazolyl- (3)] - 0.0-diethyl-thiophosphate 0- [1-phenyl-5-N, N-dimethyl Tylocarmanoyl-1,2,4-triazolyl (3) - O-ethyl-ethylthiophosphonate 0- [1-isopropyl-5-ethoxy-carbomyl-1,2,4-triazolyl- (3)] 0- [1-phenyl-5-ethoxycarbonyl-1,2,4-triazolyl- (3)] - -0.0-dimethyl-thiophosphate O- [1-phenylphosphate -0,0-diethylthiophosphate -5-ethoxycarbonyl-1,2,4-triazolyl (3) - -0,0-dimethyl phosphate 0- [1-fe nyl-5-ethoxycarbonyl-1,2,4-triazolyl (3) - -0,0-dimethyl-phosphate O- [1- (3'-chlorophenyl) -5-ethoxycarbonyl-1,2, 4-triazolyl- (3) - 0.0- (Jb1-1 ethyl-thiophosphate 'E' "0- [1-isopropyl-5-ethoxycarbonyl-1,2,4-triazolyl- (3) ] -O-ethyl-ethylthio-phosphonate 0- [1-phenyl-5-NN-dimethylcarbamoyl-1,2,4-triazolyl- (3)] -0- dimethylthiophosphate 0- O- [1-phenyl-5-methoxycarbonyl-1,2,4-triazolyl- (3)] -0.0-diethylthiophosphate O- [1-phenyl-5-ethoxycarbonyl-1,2,4 -triazolyl- - (3)] - O-n-propyl-methyl-thiophosphate Physical properties melting point or 20 n D 90 ° -91 ° C 54 ° -56 ° C rioOf \ nCs ~ and 88 ° -90 ° C 52 ° —53 ° C \ 20 n = 1.5495 D 20 n = 1.4834 D n '* = 1.5462 D n2 ° = 1.5215 D n "= 1.5085 D 20 n = 1.5412 D 20 n = 1.4927 D 58 ° -02 ° C 58 ° -61 ° C 20 n = 1.5340 D82 931 19 Example II. Insecticidal action through the food path of tobacco bushes and potatoes is sprayed with a 0.05% aqueous emulsion of the active substance, obtained from an emulsion concentrate. After drying the applied agent, the owl caterpillar (Spodoptera litoralis) is placed on the tobacco plants, and on potato bushes the larvae of the Colorado potato beetle (Leptinotarsa Lecemlineata). The tests are carried out at a temperature of 24 ° C and 60% relative air humidity. Tables II and III give the results of further tests carried out with the Colorado beetle larvae and the owl caterpillars, with where the name of the active ingredient used is listed in column I, and the time in hours in column II, after which 100% of the test animals assume the dorsal position. Example III. Systemic insecticidal action. For systemic insecticidal activity, rooted bean plants (Vicia fabae) are placed in a 0.01% aqueous active ingredient solution made with a 10% emulsion concentrate. After 24 hours for the over- Table II 20 Table III Active substance 0- [1-phenyl-5-ethoxycarbonyl-1,2,4-triazolyl- (3)] - 0.0-diethyl-thio-phosphate] O- [1-phenyl-5-carbamoyl-1,2,4-triazolyl (3)] - 0.0-diethyl-thiophosphate O- [1-phenyl-5-ethoxycarbonyl-1,2,4 - -triazolyl- (3) - O-ethyl-ethylthiosophonate I O- [1-phenyl-5-N-methylcarbamoyl-1,2,4-triazolyl- (3)] -O-ethyl-ethyl ! o- j thiophosphonate. 10- [1-phenyl-5-N, N-dimethylcar- 1 bamoyl-1,2,4-triazolyl- (3)] - O-ethylethylthiophosphonate J 0- [1- phenyl-5-ethoxycarbonyl-1,2,4-J-triazolyl (3) -0,0-dimethyl-thio-phosphate O- [1, phenyl-5-ethoxycarbonyl-1,2,4-1 - triazolyl (3) - 0.0-dimethylphosphate 10- [1-phenyl-5-ethoxycarbonyl-1,2,4-i-triazolyl (3)] - 0.0-diethylphosphate O- [1- (3'chlorophenyl-5-ethoxycarbonyl-1,2,4-triazolyl- (3)] - 0.0-diethylthiophosphate O- [1-isopropyl-5-ethoxycarbonyl- 0.0-diethyl-O- [2-isopropyl-6- 1-methyl-pyrimidinyl- (4)] -thio- -1,2,4-triazolyl (3) - O-ethyl] -ethylthiophosphonate \ phosphate Time period in hours for Colorado potato beetle larvae 1 2 1 2 1 1 1 2 1 2 24 10 15 20 25 30 45 55 Active ingredient 0- [1-phenyl-5-ethoxycarbonyl-1,2,4- - triazolyl- (3)] - O, O-diethyl-thiophosphate, O- [1-phenyl-5-N-methylcarbamoyl- 1,2,4-triazolyl- (3)] - O, O, diethylthiophosphate O- [1-phenyl-5-ethoxycarbonyl-1,2,4-triazolyl- (3)] ethyl-ethyl thio-phosphonate O- [1-phenyl-5-N, N-dimethylcarbamoyl-1, 2,4-triazolyl- (3) J -0.0-ethylthiophosphonate 0- [1-isopropyl-5-ethoxycarbonyl-1,2,4-triazonyl- (3)] - 0.0-diethylthiophosphate O- [1-phenyl-5-ethoxycarbonyl-1,2,4-triazolyl (3)] - 0.0-dimethyl-thiophosphate O- [1-isopropyl-5-ethoxycarbonyl- 1,2,4 -triazolyl- (3)] - O-ethyl-ethylthio-phosphonate O- [3-N-methylcarbamoyl-propenyl (2)] - O, O-dimethyl acid ester | phosphorus (Azodrin) Period of time in hours for owl caterpillars 24 24 24 24 5 24 5 48 aphids (Aphisfabae) are placed on the ground parts of plants. Insects are protected with a special device against direct action of the active substance and by the gas phase. The tests are carried out at a temperature of 24 ° C and 70% relative air humidity. The results obtained are illustrated in Table IV, in which the active substance is listed in column I, and the mortality of individuals is listed in column II in column II. Table IV Substance active 0- [1-phenyl-5-ethoxycarbonyl-1,2,4-triazolyl (3)] - 0,0-diethyl-thio-phosphate O- [1-phenyl-5-N-methylcarbamoyl-1 , 2,4-Triazolyl (3) - O, O-diethyl-thiophosphate O- [1-phenyl-5-carbamoyl-1,2,4-triazolyl (3)] - O, O-diethyl -thio-phosphate 0- [1-phenyl-5-ethoxycarbonyl-1,2,4-triazolyl- (3)] ethyl-ethylthiophosphonate Mortality after 24 hours for aphids 80 80 100 10021 Active substance 0- [1-Phenyl-5-N-methylcarbamoyl-1,2,4-triazolyl- (3)] - O-ethyl-ethylthiophosphonate 0- [1-phenyl-5-N, N- dimethylcarbamoli-1,2,4-triazolyl (3) - O, O-, dimethyl-thiophosphate O- [1-phenyl-5-N, N-dimethylcarbamoyl-1,2,4-triazolyl- (3)] - O-ethylethylthiophosphonate 0- [1-isopropyl-5-ethoxycarbonyl- 1,2,4-triazonyl- (3)] - 0 O- [1-phenyl-5-ethoxycarbonyl-1,2,4-triazolyl- (3)] - 0- dimethylphosphate O- [1-phenyl-5-ethoxycarbonyl, O-diethylphosphate -1,2,4-triazolyl (3) - O, 0-diethylphosphate O- [1-isopropyl-5-ethoxycarbonyl -1,2,4-triazolyl (3)] - 0- ethyl ethyl thiophosphonate 0- [1-phenyl-5-N, N-dimethylcarbamoyl-1,2,4-triazolyl- (3)] -0- [1-dimethyl-thiophosphate] 0- [1-phenyl- 5-methoxycarbonyl -1,2,4-triazolyl- (3)] - O, O-diethyl-thiophosphate, O, O-dimethyl-O- [1-phenyl-1,2,4- | -triazolyl- (3)] -thiophosphate. Mortality after 24 hours for aphids 100 90 100 100 90 100 100 100 100 0 Example IV. Effect of the active ingredient on all developmental forms of pests of leiomyosus (Tetrańus urticae). In order to test the nematocidal activity of the active ingredient, bean leaves infested by adults and individuals in heat as well as red neck eggs (Tetranyus urticae) were used. The leaves were treated with the active compound in the form of a 0.05% aqueous emulsion formulation made from a 25% emulsion concentrate. The research was carried out on individuals of the strains resistant to the action of phosphoric acid esters. The evaluation of the results obtained after 6 days is shown in Table V, in which the% mortality is given. Activity against ticks (Boophilus micriplus) and their development forms. The tests were carried out on 10 mature individuals, while immersing them for a period of 3 minutes in an aqueous emulsion of the active substance at the concentration given in column II of the Table, and then the ticks were kept at a temperature of 27 ° C and 80 ° C, relative humidity at and after 5, 10 and 15 days the number of eggs was determined. The results obtained are shown in Table VI. 931 22 Table V Active substance 0- [1-phenyl-5-carbamoyl-1,2,4-triazolyl- (3)] - 0.0-diethylthiophosphate 0- [1-phenyl- 5-ethoxycarbonyl-1,2,4-triazolyl (3) - O-ethyl-ethylthiophosphonate 0- [1-phenyl-5-N-methylcarbamoyl-1,2,4-triazolyl - - (3)] - O-ethyl-ethyl- | Phosphonate mortality after 6 days with an active ingredient concentration of 0.05% adults 100 100 100 interstitial period 100 100 100 eggs 100 100 100 Example V. Activity against soil nematodes. The active substance according to the invention is introduced in a concentration of 50 ppm into the soil contaminated with root yellow nematodes (Meloidogyne Avenaria) and thoroughly mixed. Tomato seedlings are planted directly into the soil prepared in this way, with part of the soil being allocated tomato seeds are sown, which seeds are sown but not until 8 days after soil preparation. The activities are assessed 28 days after planting or sowing, counting the number of yellow bubbles on the roots of the experimental plants. The obtained results showed that; The compounds prepared according to Example I exhibit nematocidal activity. Example VI. Fungicidal activity. Fighting Piricularia oryzae Bri. et Cav. 45 a) Protective action. Rice seedlings, placed in the greenhouse, were sprayed with an aqueous suspension containing 0.05% of the active ingredient. Pb after 2 days these plants were infected 50 Table VI Active substance 0- [1-phenyl-5-N, N-dimethylcarbamoyl-1,2,4-triazolyl- (3 /] - 0.0, - diethylthiophosphate Concentration of active substance% 0.1 0.05 0.025% of eggs deposited after 5 days 0 0 0 10 days 0 0 0 15 days 0 0 082 931 23 conidial spores Piricularia oryzae Bri et Cav and then, after a 5-day incubation period in a moist room, the degree of fungus was determined. b) curative effect. Rice seedlings, placed in a greenhouse and infected with Piricularia oryzae Bri conidial spores. et Cav, after 2 days from the time of infection, an aqueous suspension containing 0.05% of the active substance was sprayed, and then, after a 5-day incubation period in a humid room, the degree of fungus was determined. Activity against Phytophtora infestans on Solanum Lycopersicum. The same species and development stage of Solanum Lycopersicum plants are treated with a suspension containing 0.05% of the active substance, made of a wettable powder. After the preparation applied to the plants has dried, the dry plants are sprinkled into In the wet, the zoospore suspension of Phytophtora unfestans and the plants are left for 6 days in the greenhouse at 18-20 ° C and 95-100 ° C with relative air humidity. After the above-mentioned period of time, typical spots appear on the leaf surface. The effectiveness of the agent is assessed by calculating the number of stains and their area. The results of the above tests a) and b) showed that the compounds according to the invention are characterized by good fungicidal activity. PL PL

Claims (1)

Claims 1. A pesticide, characterized in that the active substance comprises 0.1-95% of a compound of the general formula I, in which Rx represents a hydrogen atom, an alkyl, alkenyl, alkynyl, phenyl or cycloalkyl radical, —COORj, —CONfRi) (R4) or —C = N, R3 is an alkyl, alkoxy or phenyl radical, R4 is an alkyl radical and X is an oxygen or sulfur atom, and 5-99.9% of suitable carriers and / or other extras. 2. The measure according to claim the active ingredient has a compound of formula 13. 3. The agent according to claim 1, The active substance according to claim 5 has a compound of formula 14. 3. The agent according to claim 5, the active ingredient is the compound of formula 15. 5. The agent according to claim 1, the active ingredient is the compound of formula 16. 6. The agent according to claim 15, the active ingredient is the compound of formula 17. 7. The agent according to claim 1 the active ingredient is the compound of formula 18. 8. A composition according to claim 1, The active ingredient is the compound of the formula 19. The agent according to claim 20 the active ingredient is the compound of formula 20. 10. A composition according to claim 1 the active ingredient is the compound of formula 21. 11. The agent according to claim 22 is the active ingredient of the compound of formula 22. the active ingredient is the compound of formula 23. The active ingredient is the compound of formula 24. the active ingredient is the compound of formula 25. the active ingredient is the compound of formula 26. the active ingredient is the compound of formula 27.1, characterized in that of the general formula I, characterized in that, of the general formula I, characterized in that, of the general formula I, characterized in that General formula I, characterized in that with general formula I, characterized in that with general formula I, characterized in that with general formula I, characterized in that with general formula I, characterized by A method according to claim 1, characterized by the general formula A method as claimed in claim 1, characterized in that with general formula 1 a-, 1 characterized in that with general formula 1 a-, 1 characterized in that with general formula 1 a-. A method according to claim 1, characterized by the general formula A method according to claim 1, characterized by the general formula A method according to claim 1, characterized in that, with the general formula 1 a-N -N 1 I II R j-CyC-OP ii / R 3, OR, Formula 7 R c-NN x 5 I II t R 1 -C 2, X -0-P / K7 * N, OR; Formula 2 R, -N -N 1 I II R2- (X, X-OH Formula 3 OR 'R00C-C-OR' I., OR Formula '5 HjN-CO - ^^ OH Formula 7' Hd-P ii / R / K3 N OR / Formula 4 H5C2O-C0- ^ N ^ OH N — N IVzor 6 JL 1 HX-NH-G0 ^ N ^ OH Hfeor # (H3C) 2N-CO ^ N ^ OH Formula 9 Cl Ii h5c2o Formula K) ONN HcCO-CO 3 SAoH Formula 11 CH 3 1 CH, CH, H 5 CO 2 -C 0 / N NN XX Formula 1282 931 c 2 occ 4 -op 2. o 2n5 Formula 13 I! L rt i / 0C2H5 CH ^ -C ^ CvC-0-P lVzor & ^^ I II »NH2 ~ CC ^ C-0-P 0 Formula V / 0C2H5 NOC2H5 ^ - ^ I li« / 0C2H5 CHrNH «cV-0« Px 0 mor 16 N / N — N s CH3X | M x0C2H5 0 Formula ^ / 7 CH3 \ CH, 0 N-N I !! H / OCoHc NC- (kKC-0-P. 2 5 CtHi 2n5 Wzdf 7S CH 3N ^ pu - CH3 / CH — N — NSI / OC2H5 C.HfOJ-CyC-OP ^ '2n5 1-KzOr / 9 NN s ^ i li aaCH3 c2Hso-cc ^, xo- ~ p ¦0 Formula 2082 931 C, HE0-C-CyC-0-P (3 / 2n5v II O ^ OCH. Formula 21 NN 0 i Y./OCoHc G2H50-C- CVC ^ 0-PN0CH O? '5 Formula 22 CL N —N o I 1 l / 0C2Hc C2H5-0-C-CVC-0-PXoCoH 2n5 Jtóresr 23 ~ N - N s CH / N | CVC ° P \, O 'OCH, M / Zdr2? N ~ N 11 N NOC2H? O Formula 26 CH-NN OC, H "/ uu2nc CH3X CH3 / i ii ii. C2H50-C-CvC-0- ^ O' Formula 24 H5C20-C -CwC-0-PW MfeV- 27 \ f82 931 ERRATA Lam 20, v. 20 It is: -00-ethyl-thiophosphonate It should be: -diethyl-thiophosphate LZG, Plant No. 1. Order 764/76, circulation 105 copies. Price PLN 10 PL PL