DE2210092A1 - Pesticides - Google Patents

Description

Pesticides

The present invention relates to new trifluoromethylphenylthlolphosphoric acid esters, their manufacture and use for pest control.

The trifluoromethylthjolphenylphosphoric acid esters correspond to the formula
X

(D

where R ₁ and R "each signify alkyl and X and Y each signify oxygen or sulfur.

The alkyl chains in question for R and Rp contain 1 to K carbon atoms and can be branched or straight-chain.

Examples of such alkyl chains include methyl, ethyl propyl, isopropyl, n-, i-, sec- and tert. Butyl.

Of particular importance are the connections

Formula _γ

Ti Π ην

/ -s-Λ 9 (id

^R /

209840/1183

wherein R ₃ and R ^ are each C _± -C alkyl and X and Y are each oxygen or sulfur.

Examples of compounds of formula (II) are i.a.

^CF 3
R ¹ - s - <nT ~ ^> (in)

(V)

wherein R ¹ , R ", R ¹¹¹ each

OS ₀

H H y

(CH ₅ O) ₂ -P-; (C ₂ H ₅ O) ₂ -P-; CnC ₃ H ₇ O) ₂ -P-;

? CH ₃ Oj CH ₃ Oj C ₂ H ₅ Oj (11C ₅ H ₇ O) ₂ -P- ; P-; P- or P C ₂ H ₅ O (n) c H ₇ O (1I) C ₃ H ₇ S

The compounds of the formula I can after per se
known methods can be produced in which, for example:
a) a salt of a compound of the formula

P-S-M

r /

wherein R, R ^, γ and X have the meaning given for the formula I.
and M has a metal atom, preferably an alkali metal atom,
like sodium or potassium means, in a two-phase system

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10-1OO ° C, preferably at 20-70 ⁰ C, can act on a diazotized trifluoromethylaniline. This reaction is catalyzed by copper.

A two-phase system is understood to mean a solution of water and a water-immiscible organic solvent. Examples of such solvents are ether, chloroform, methylene chloride, ethylene chloride, petroleum ether, benzene, toluene, xylene, chlorobenzene, dichlorobenzene and nitrobenzene.

b) a compound of the formula

P-H (VII)

R ₂ O

with the compound of the formula

Gl-S - ^ ~ s / (VIII)

reacts in the presence of an acid-binding agent.

In the formula (VI), symbols R-, Rp and X have the meaning given for the formula I.

The following bases, for example, can be used as acid-binding agents: tertiary amines, such as triethylamine, dimethylaniline, pyridine, pyridine bases; inorganic bases such as hydroxides and carbonates of alkali and alkaline earth metals, preferably sodium and potassium carbonate. This reaction is preferably carried out in inert solvents. For example, the following are suitable for this: aromatic hydrocarbons,

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such as benzene, toluene, benzines, chlorobenzene, polychlorobenzenes, bromobenzenes; suitable chlorinated alkanes having 1 to 3 carbon atoms; Ethers such as dioxane; Tetrahydrofuran; Esters such as ethyl acetate; Ketones such as methyl ethyl ketone, diethyl ketone and nitriles such as acetonitrile.

Dfe starting materials of the formulas (VI), (VII) and (VIII) as well as the trifluoromethylanilines are known compounds which are obtained by known processes described in the literature can be produced. The diazotization of the trifluoromethylanilines is carried out according to methods known per se.

The active ingredients of the formula I are suitable for combating a wide variety of animal and vegetable pests. They can be used, for example, as anthelmintics, viricides, fungistats or bacteriostats. they seem but above all against all stages of development, such as eggs, larvae, nymphs, pupae and adults of insects and representatives of the order Akarina, such as mites and ticks.

The compounds of the formula I can, for example, be used against the following insects or of the order Acarina can be used:

Insects of the families: Teltigonidae, Gryllidae, Gryllotalpidae, Blattidae, Peduviidae, Phyrrohocoriae, Cimicidae, Delphacidae, Aphididae, Diaspididae, Pseudococcidae, Scarabaeidae, Dermestidae, Coccinellidae, Tenebrionidae, Chrysomelidae, Bruchidae, Tineidae, Noctindae, Lymatriidae, Pyralidae, GuIicidae, Tipulidae, Stomoxydae, Trypetidae, Muscidae, Calli-

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22 ι ΰ Ο 9

phoridae and Pulicidae as well as acarids of the families Ixodidae, Argasidae, Tetranyehidae and Dermanyssidae.

The insecticidal and / or acaricidal effect can be substantially increased by adding other insecticides and / or acaricides broaden and adapt to given circumstances.

The following active ingredients, for example, are suitable as additives:

Organic phosphorus compounds

Bis-0, O-diethylphosphoric anhydride (TEPP) dimethyl (2,2,2-trichloro-1-hydroxyethy)) phosphonate (TRICHLORFON) 1,2-dibromo-2,2-dichloroethy] diniethyl phosphate (KALED) 2,2-dichlorovinyidimethylphosphate (DICHLORPHOS) Z-Hethoxycarbamyl-1-Nethylvinyldimethylphosphat (MEVINPHOS) Di «eihyl-1-inethyI-2- (methylcarbamoyl) viny] pfiosphai_c_is_ (MONOCROTOPHOS) a-iDimethoxyphosphICloxyJ-amid (DimethoxyphosphICloxyJ-f ^ N DimethoxyphosphICloxyJ-f ^ N-dimethoxyphosphICloxyJ-f ^ N Chloro-2-di-aihy1carbamoy1-1-meihy] vinyldimethyl phosphate (PHOSPHAHIDON) O, 0-diethyl-O (or S) -2- (ethylthio) ethylthiophosphate (OEETON) S-ethylthioethyl-0,0-diiiiethyl-dithiophosphate (THIOnIETON) OO-diethyl-S-ethyl mercaptoirethyldithiophosphate (PHORATE) O ₁ O-Dlithy1-5-2- gthylthio) ethyl dithiophosphate (DfSULFOTON) O, 0-Dimethyl-S-2- (ethylsulfinyl) ethyl-ethylthiophosphate (.0.0-Ethylthiophosphate) -Dimethyl-S- (1,2-dicarbäthoxysthyI dithiophosphat (ItfALATHION) 6 _v 0 _f 0,0-Tetraäihyl-S _f S ^l -aeihyIen-bfs- dithiophosphat (ETHION) O-Ethy1-S, Sd i propy1dithiophosphat OjO-Dimethyl -S-fN-methyl -N-formylcarbaiüoylinethyD-dithiophosphat (FORMOTHION) 0,0-Dimethyl-S- (N-methylcarbamoylmethyl) dithiophosphat (DIHETHOAT) 0,0-Dimethyl-Op-nitrophenylthiophosphat (PARATHION-METHYL) 0,0-Diethy1-0-p- nitropheny1thiophosphate (PARATHION) O-ethy1-0-p-nitrophenylphenylthiophosphonate (EPN) 0,0-dimethyl-0- (4-nitro-m-tolyl) thiophosphate (FENITROTHION) OjO-dimethyl-O ^^ - S-trichlorophenylthiophosphate (RONNEL ) 0 ~ ethyl-0,2,4,5-trichlorophenylethylthiophosphonate (TRICHLORONATE) 0, O-dimethyl-0-2,5-dichloro-4-broniphenylthiophosphate (BROMOPHOS) 0,0-dinethyl-0- (2,5- dichloro-4-iodophenyl) thiophosphate (IODOFENPHOS) 4-tert. Butyl-chlorophenyl-N-ethyl-O-raethylanidophosphate (CRUFOMAT) 0,0-DlmethyI-0- {3-methyl-4-methylmercaptopheny]) thiophosphate (FENTHION) isopropylamino-O-ethyl-O - ^ - methylmercapto-S -methylphenylJ-phosphate 0,0-diethyi-Op- (nethylsulfinyl) phenyl -thiophosphate (FENSULFOTMON) 0-p- (dimethylsulianido) phenyi 0,0-dimethylthiopnosphate (FAKPHUR) OjOjO'.O'-tetra-ethyl-O.O '-thiodi-p-phenylenethiophosphate O-ethyl-S-phenyl-ethyldithiophosphonate 0,0-dimethyl-0-! 4-dichlorophenyl) vinyl diethyl phosphate (CHLORFENVINPKOS) 2-chlorine -! - (2, A, 5-trichlorophenyl) vinyl dimethyl phosphate 0- (2-chloro-1- (2,5-dichlorophenyl) vinyl-0,0- diäihyHhiophospiiai Phenylglyoxylonitriloxiin-O ^ -diäthylthJophosphat (PHOXIM)

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OO-diethyl-OO-chloM-inethyl-Z-oxo ^ -Hl-benzopyran-T-yl) thiophosphate (COUMAPHOS) 2 _f 3-p-0 «oxanedithiol-5, S-bis (0,0-diethyldithiophosphate) (DIOXATHION) S-fie-Chior-Z-oxo-a-benzoxazolinyDmethyllOjO-diethyldithiophosphate (PHOSALOH) 2- (0lethoxyphosphinylinino) -l, 3-dithiolane 0,0-Diuethyl-S- [2-ir, ethoxy-1,3, 'i-thiadiazol-5 - (* H) -onyl- (4) -iBethyl] dithiophosphate 0,0-Diaethyl-S ^ phthalimidonethyl-dithiophosphat (IMIDAN) 0,0-diethyl-0- (3,5, β-trich) or-2-pyridyl) thiophosphate O, O-diethyl-O-2-pyraziny] thiophosphate (THIONAZINE) 0,0-Dläthyl-0- (2-isopropyM-methyl-6-pyriBidylJthiophosphat (DlAZINOH) O.O-diethyl-O-te-quinoxalyothiophosphate 0,0-D1aethy1-S- (4-oxo-l, 2,3-benzotriazine-3 (4H) -y! Inethyl) -dithiophosphate (AZINPHOSMETHYL) 0,0-diethyl-S- (4-oxo-l, 2,3-Benzotriazine-3 (4H) -y1methyl) -dithiophosphate (AZINPHOSAETHYL) S - [(4,6-diaaiino-s-triazin-2-yl) methyl] -0,0-dimethyldithiophosphate (BENAZON) OO-Oiaethyl -O-ia-chloM-nitrophenyUthiophosphat (CHLORTHIONE) 0 _f 0-DlBethy1-0 (or S) -2- (ethylthioethyl thiophosphate (DEMETON-S-HETHYL) 2- (0,0-Diiethyl-phosphoryl-thioirethyl) -5-iiethoxy-pyrone-4-3 _f 4-dichlorobenzyl-triphenylphosphonic chloride 0,0-0iethyl-S- (2,5-dichlorophenyHhioinethyl) dithiophosphate (PHENKAPTON) 0,0-D1ethyl-0 - (* - methyl-cuinarinyl-7) -thiophosphate (POTASAN) 5-ABino-bis (dieethylapido) phosphinyl-3-phenyl- _{1,2 f} mriazole (TRIABIPHOS) ■ N-BethyT -5- (0,0-diBethylthiolphosphoryl) -3-thiavaleraraid (VAMIOOTHION) 0,0-diethyl-0- [2-dimethylamino-4-methylpyrmidyl- (6)] thiophosphate (DIOCTHYL) OO-diethyl-S-f-methylcarbamoyliiiethyD thiophosphate (OMETHOAT) O-Aethyl-O-iS-quinolinyD-phenylthiophosphonate (OXINOTHIOPHOS) O-Hethyl-S-Biethyl-anidothiophosphate (KONITOR) 0-methyl-0- (2,5-dichloro-i-bro (iiphenyl) -benzothiophosphonate (PHOSVEL) 0,0,0,0-tetrapropyldithiopyrophosphate

S-iDiBethoxyphosphinyloxyJ-N-niethyl-N-nethoxy-cis-crotonanide 0,0-DiBethyl-S- (N-äthykarbaraoy] methyl) dithiophosphate (ETHOAT-METHYL) 0.0-0 diethyl-S- (N-isopropylcarbamoy] ir, ethyl) -dithiophosphate (PROTHOAT) S-N-d-Cyano-l-methylethyl) carbanoylmethyl diethylthiol phosphate (CYANTHOAT) S- (2-acetamidoethyl) -G, 0-diniethyldithiophosphate Hexaiethylphosphoric acid triamide (HEMPA) 0,0-DiBethyl-0- (2-chloM-nitrophenyl thiophosphate (DICAPTHON) OO-Dinethyl-Op-cyanophenyl thiophosphate (CYAfIOX) O-ethyl-Op-cyanophenylthiophosphonate 0,0-diethyl-0-2, A-dichlorophenylthiophosphate (DICHLORO-THIophosphate ) 0,2,4-dichlorophenyl-u-inethy 1 isopropylaynidothiophosphate 0,0-dlethyl-0-2,5-dichloro-4-brominopheny] thiophosphate (BROMOPHOS-AETHYL) diiethyl-p- (ethylthio) phenyl phosphate OjC-DUethyl -Op-sulfamidophenyl thiophosphate Or {p- (p-chlorophenyl> zopheny)] 0,0-diiiiethylthiophosphate (AZOTHOAT) O-EthyI-S-4-chloropheny1-ethy1d i thiophosphonate O-lsobutyl-Spjhlorophenyl-ethyl-phosphonate-0,0 -Sp-chloropheny1thiophosphate OO-diaethyl-S-ip-chlorophenylthiomethyl-dithiophosphate OO-diethyl-p-chlorophenylinercaptoirethyl-dithiophosphate (CARBOPHENOTHION) 0,0 -diiethy1-Sp-chiorphenyIthiomethyl-thiophylbosphate-OO-D-PHiophosphine-S-phenylthiomethyl-thiophylbosphate-OO-Jd-PHO-phosphine-S-phenyIthiomethyl-thiophylbosphate-OO-ethoxy O ₁ O-diethyl-S- (carbof1uoräthoxy-pheny1 «ethyl) -di thiophosphate O _f O-Diaethyl-S- (carboisopropoxypheny! Niethyl) -dithiophos phat 0,0-diethyl-7-hydroxy-3,4-tetraseihyien-ccj (nariny1 -thiophosphate (COUBITHOAT)

0,0-0-ethyl-0- (5-phenyl-3-isoQX3zoly] thiophosphate

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2- (Diethoxyphosphinyl1iinoM-methyl-1,3-dithiolane

Tris- (2-Bethyl -] - aziridinyl) -phosphine oxide (HETEPA) S- (2-chloro-1-phthalimidoethyl) -0,0-diethyldithiophosphate N-hydroxynaphtha] iraido diethyl phosphate DiBethy] -3,5,6-trich] or-2-pyridyiphosphate

0,0-Dl «ethyl-0- (3,5,6-chloro-2-pyndyl) thiophosphate S- 2- (ethylsulfony]) ethyl dimethylthiolphosphate (DIOXYDEHETONE-S-HETHYL) diethyl-S- 2- (ethylsulfinyl ) ethyl dithiophosphate (OXYDISULFOTON) bis-OjO-diethylthiophosphoric anhydride (SULFOTEP) diethyl 1,3-di (carbonethoxy) -] - propen-2-yl phosphate

Diwthyl- (2,2,2-trichlor-1-butyroyloxyäthy1) phosphonat (BUTONATE)

0,0-diethyl-0- (2,2-dichloro-1-methoxy-vinyl) phosphate

Bis (dinethy1an; ido) fluorophosphate (DlMEFOX) Sji-dichlorobenzyl-triphenylphosphonium chloride OiBethyl-N-iiethoxymethylcarbainoylnethyl-dithiophosphat - ■ (FORMOCARBAfJ)

0,0-diethyl-0- (2,2-dichloro-1-chloroethoxyv1nyl) phosphate 0,0-DlBethyl-0- (2,2-dichloro-1-chloroethoxyviny1) phosphate 0-ethyl-S, S-diphenyldithio] phosphate

O-ethyl-S-benzyl-phenyldithiophosphonate

0,0-diethyl-S-benzymhiolphosphate

O.O-Dinethyl-S-iA-chlorophenylthioniethyDithiophosphate (BETHYLCARBOPHENOTHION)

0,0-diethyl-S- (ethyithioniethyl) dithiophosphate

DHsopropyl ainofluorophosphate (MIPAFOX)

0,0-Oiiethyl-S- (norpholinylcarbainoyliethyl) dithiophosphate (MORPHOTHION)

BisaethyIan1do-pheny] phosphate

0,0-diethyl-S- (benzenesulfonyl) dithiophosphate 0,0-Diiethy1- (S and O) -Ifhy1sulίiny1äthylthiophosphat

O _f O-diethyl-0-4-nitrophenyl phosphate Triethoxy-isopropoxy-b1s (thiophosphinyl) disulfide

2-methoxy-4H-1,3,2-benzodioxaphosphorin-2-oxide

Okiaiethylpyrophosphoraaid (SCHRADAN) Bis (diiethoxythiophosphinylsulfido) phenylmethane

p / N'-tetraiethyldiaaidofluorophosphate (DIMEFOX)

O-phenyl-0-p-nitrophenyi-nethanthiophosphonate (COLEP)

0-IIethy1-0- (2-chloro-Mert. Butyl-phenyl) -N-methylaaiidoth1ophosphate (HARLENE) 0-ethyl-0- (2, <- dichlorophenyl) -phenylthiophosphonate

O ^ iäthyl-O-ii-methylaercapto-S.S-diniethylphenyD-thiophosphate A, V-bis (0,0-dioethylthiophosphoryloxy) -diphenyldisu] fid OjO-Di-fp-chlorithyD-O-O-chloroM-iiethyl-cuiiiarinyl -7) phosphate S- (l-PhthaMnidoethyl) -0,0-diethyldithiophosphate O.O-Ethyl-O-fS-chloro-i-diethylsulfanylphenyD-thiophosphate

O-methyl-0- (2-carbisopropoxyphenyl) anidothiophosphate

S-iO.O-OirethylphosphoryD-a-chlor-bicycloO ^ .Oj-heptadiend.S)

0-methyl-0- (2-i-propoxycarbonyl -1-ethylvinyI) ethylaniidothiophosphate

Hitrophenoie I. Derivatives

^, B-Dinitro ^ -inethylphenol, Na-saiz [Oinitrocresol] Dinitrobutylphenol (2.2 ^f , 2 "triethanolanine salt) 2 CyclohexyM ^ -Dinitrophenoi [Dinex] 2- (1-l-ethy] heptyl) -4,6 dinitrophenyl-crotonate [Oinocap] 2 sec-butyl-AjG-dinitrophenyl-S-iiethyl-butenoate [Binapacryl] 2 sec-butyMjß-dinitrophenyl-cyclopropionate 2 sec-butyl-ijB-dinitrophenyl-isopropyl-carbonate [dinobutone]

209840/1183

Various pyrethrin I pyrethrin II 3-allyl-2-methyl-A-oxo-Z-cyclopenten-l-yJ-chrysanthemumat (allethrin)

B-chioriperonyl-chrysanthemumate (barthrin)

2, A-dimethylbenzyl-chrysanthemuraat (dimethrin) 2,3,4,5-tetrahydrophthal iraidotnethy] chrysanthemuraat 4-chlorobenzyl-4-chlorophenyl sulfide [chlorine surfactant] 6-BethyI-2-oxo-1,3-dithiolo- [4,5-b] -quinoxaline [quinomethionate] (D-S - ^ - FurfuryO ^ -methyM-oxocyclopenW-enyldMcis + trans) chrysanthemum monocarboxylate [furethrin] 2-pivaloyl-indan-1,3-dione [pindon]

N '- (4-chloro-2-ynethylphenyl) -N, N-dimethylforinamidine (chlorophenamidine)

4-chlorobenzyl-A-fluorophenyl sulfide (fluorosurfactants) 5,6-dichloro -] - phenoxycarbanyl-2-trifluorotethylbenzimidazole (Fenozaflor) i-chlorophenyl-p-chlorobenzenesulfonate (Ovex) p-chlorophenyl benzenesulfonate (Fenson) p-chlorpheny] -2,4,5-trich] orpheny] sulfon (Tetradifon) p-chlorophenyl-2,4,5-trichlorophenyl sulfide (Tetrasul) p-chlorobenzyl-p-chlorophenyl sulfide (chlorine surfactants) 2-Thfo-l, 3-dithiolo - (, 5-6) quinoxal in (Thioquinox)

Prop-2-ynyl- (4-t-butylphenoxy) -cyclohexylsulfit (Propargil) Fomainidine

l-0imethy1-2- (2 '- (nethy) -A ¹ -chlorophenyl) -formamidine (chlorphenamidine) l-llethyl-2- (2-methyl-4 ^{t 1} -chlorophenyl) -forinaniidin l-methyl-2- ( 2 ^t -methyl-4'-bromopheny1) -formamidine l - «! ethyl-2- (2 ', V-dir; ethylphenyl) -foriramidine 1-n-butyl-l-methyl-2- (2 ^l -methyl-V-chlorophenyl) -formamidine I-Hethy 1 - 1 - {2 '-me thy 1 -4' -ch 1 oran i 1 i η o-! Re thy i en) 2- (2 "- methyl-4 ¹ '-chlorphenyl) -forraamidine in-butyl-2 - (2'-methyl-4'-chlorophenyl-iinino) -pyrrolidine

urea

N-2-methyl-4-chlorophenyl-N ^I , N'-diraethyl-thfourea Carbanate ■ ■

l-naphthyl-N-methylcarbamate (CARBARYL) 2-butynyl-A-chlorophenyl carbamate 4-Di «ethylamino-3,5-xy Iy 1-N-methyl carbamate

A-Oimethylainino-3-tolyl-N-methylcarbarate (AMINOCARB)

4- «ethyHhio-3,5-xylyl-N-nethylcarbaaat (METHlOCARB) 3, A, 5-trimethylphenyl-N-methylcarbarate 2-chlorophenyl-N-methy) carbamate (CFMC) 5-chloro-6-oxo-2-norborran-carbonitrile-0- (n: ethylcarbai> ioyl) -oxiai 1- (Dimethylcarbamoyl) -5-3iethyl-3-pyra2olyl-N, N-diinethylc3rbaii) at (DIMETILAN) 2,3-0ihydro-2,2-dimethyl-7-benzofuranyl-N-diethylcarbamate (CARBOFURAN)

Z-Methyl ^ -nethylthio-propionaldehyde-O-diiethylcarbamoyD-oxime (ALDICARB)

8-Quinaldy1-N-methylcarbamate and its salts

Methyl 2-isopropyl-4 - ((rethylcarbaraoyloxy) carbanilate

■ - {1-AethylpropyUphenyl-N-methylcarbaiiat 3,5-di-tert-butyl-N-methylcarbamate ■ - (1-methylbutyl) phenyl-N-methylcarbainate 2-isopropy 1 phenyl-fi-methyl 1 carbanate 2-sec.Butyl phenyl-N-methy Icarbaraat ■ -Toiyl-N-methyl carbamate

2,3-Xy1y1-N-methylcarbamate

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3-Isopropy 1 pheny 1-N-methylcarbaniate 3-tert-Butylphenyl-N-methylcarbamate 3-sec -Buty Ipheny1-N-methy1carbamate 3-Isopropy1 -5-methy1pheny1-N-methylcarbamate (PROMECARB) 3,5-Diisopropyipheny1- N-methylcarbamate 2-chloro-5-isopropy] phenyl-N-methylcarbamate 2-chloro-4,5-dimethylphenyl-N-methylcarbamate '

2- (1,3-Dioxolan-2-yl) phenyf-M-methylcarbamate (DIOXACARB) 2- (4,5-0i! T.ethyl - !, 3-dHXoTan-2-yl) ph3nvl- ^f l-5iethylcarban ! at 2- (1,3-Di oxo-1an-2-y1) phenyi-N, Nd i methy1carbamat 2- (1,3-Di thiolar-2-yin, N-ciimethy "IcarDamat 2- (1,3 -Dithiolar-2-yOpfe. "Yi-N, Sd ^? N; etiiy! Carbanate 2-uropropoxyphenyl-Nn: ethy] cartanate (ARPROCARB) 2- (2-propinyloxy) phenyl-N-ir, ethylcarbanate 3-CZ Propynyl oxy) pheny1-N-methylcarbamate 2-dimethyl3rnnophenyl-N-ir.ethylcarbaniate 2-DIaT lylaminophepyl-N- ^ ethylcarbairate 4-diallylaisino-3,5-xy1y] -f .'- [re% carbanate (ALLYXiCARB) 4 -Benzothienyi-N-methy 1-carbamate 2,3-dihydro-2-methy] -7-benzofuranyl-N-: methyl carbamate 3-methyl-l-phenylpyrazol-5-yl-N, N-dimethylcarbamate l-isopropyl-3- methyIpyrazo1-5-y1-N, Nd! methy 1carbamat (ISOLAN) 2-Dimethy! a, T, ino-5,6-dimethylpyrimidin-4-yl-N, N-dimethyl-carbamate S-HethyM-dinethylaminornethyleniminophenyl-N- methylcarbamate 3, ^ - dimethylphenyl-N-methylcarbamate 2-cyclopentyl-N-methylcarbamate 3-diniethylamino-ethyleninophenyl-N-methylcarbainate (FO RMETANATE) and its salts l-methylthio-ethylimino-N-methylcarbamate (ETHOMYL) 2-Meihy I carbanioy i ox i ra ino-1,3-di thiolane S-methyl-Z-methylcarbaraoyloxiraino-ljS-oxythiolane 2- (l - Methoxy-2-propoxy Jpheny1-N-methyl carbamate 2- (l-butyn-3-yl-oxy) phenyl-N-methy] carbamate l-methylcarbamyl-l-methylthio-O-rsethylcarbamyl-formoxime l- (2 ^l - Cyanoethylthio) -0-methylcarbamyl-acetaldoxime 1-methylthio-O-carbasiyl-acetal dox in 0- (3-sec-butylphenyl) -N-phenylthio-N-methylcarbamate 2,5-diraethyI-1,3-dithioland -2- (0-methylcarbamyl) aldoxime) O-2-diphenyl-N-methylcarbamate

2- (N-Methylcarbaniy! -Oximino) -3-chlorobicyclo [2.2.1] heptane 2- (N-Methylcarbaniyl-oximino) -bicyclo [2.2.1] heptane 3-lxopropyl pheny lN-Trethyl-N-chloroacetyl carbamate 3-isopropylpheny1-N-methy1-N-methylihi oraethy1-carbamate O-iZjZ-Dimethyl-i-chloro ^^ - dihydro-T-benzofuranyD-N-methyl carbamate 0- (2,2,4-triisethyl 2, 3-dihydro-7-benzofuranyi) -N-niethyl carbamate O-naphthyl-Fi-ethyl-iJ-acetyl-carbanate 0-5,6,7,8 -tetrahydroraphthyl-N-ethyl-carbamate 3-isopropy 1-4- riethy i thi o-phenyl-N-methy I carbamat 3,5-D i nethy1-4-methoxy-pheny iN-methy1carbamat 3 ~ Methoxymethoxy-phenyl-H-tneihylcarbamax 3-Al 1 y 1 oxy pheny 1 -N- iiethy] carbania t 2-propargyioxyir.ethoxy-preny] -fi-methyl-carb2! üai 2-Αϊ lyloxypheny I - '»-" letnyl-carbamf.i 4-methoxycartc:])' l an ino-5-isopropyl pheny i «-fi" r: ji "hyl-f; arfeT '">

3,5-methylene I-4-bethoxycarbony] an i no-phenyI-N-methy1-carbaeate 2-Y-methylthiopropylt * enyl- (i-ethyl-carbaB3t

S-fo-Bethoxyoethyl-Z-propenyO-phenyl-N-methyl-carbate

2-chloro-5-tert-buty1-pheny1-N-ethyl] carbamate 4- (methyl-propargylaiino) -3,5-xylyl-N -raethyl-carbamate

A- (MethyΙ-γ-chlorallylanino) -3,5-xyIy I-N-methy1-carbaeate

4- (methyl-β-chloranylamino) -3,5-xylyl-N-methyl-carbate 1- (β-ethoxycarbonylethyl) -3-raethyl-5-pyr3zolyl-N, N-di-methylcarbaitate

S-Bethyl-A-tdiBethylaQino-oethylnercapto-BeihyleniiinoJphenyl-II-ethylcarbaeate

1,3-Bls (carbaBoyHhio) -2- (N, N-diinethylaBino) propane hydrochloride

SjSjDiiethylhydroresorcinol dinethylcarbanate

2- ^ ethyl-propargylaainoj-phenyl-N-iiethylcarbainat 2- [methyl-propargyla »ino] -pheny1-N-methy1carbama t 2- [Dipropargylaiino] phenyl-N-ethylcarbanate 4- [D1propargylaeino] -3-toly 1-fi-roethylcarbaraat 4- [DipropargylaBino] 3,5-xylyl-N-ir.ethylcarbainate 2- [AHy l-IsopropylaBinoJ-phenyl-N-methy lcarbamate 3- [A1 lyl-Isopropylaaino] -phenyl-M-raethylcarba, T5at

Chlorinated hydrocarbons γ-hexachlorocyclohexane [GAMmEXAHE; LINDAN; γ HCH] ! ^^^^^, Be-Octachlor- ^ a ^ .T ^ a'tetrahydro ^^ - Bethyleneindane [CHLORDAN] 1,4,5,6,7,8,8-Heptachloro, 3α, V7,7tt-tetrahydro -4,7- «ethylenindan [HEPTACHLOR]! ^, S ^ .IO.in-hexachlor-l. ^ Ia.SSea-hexahydro-endo ^ .i-exo-Se-diBiethanonaphthalin [AlDRIl] lZ ^^. IO. lO-hexachlor-e ^ -epoxy-l ^^ aS ^^. S ^ a-oxtahydro-exo-l. ^ - endo-SB-diBethanonaphthann [DIELDRIN] 1,2,3,4,10,10-hexachlor- 6,7-epoxy-l, 4,4i, 5 _l 6,7,8,8a-octahydro-endo-endo-5, B-diMthanonaphthaHn [ENDRIN]

In addition, the new compounds of the formula I have nematocidal properties and can be used, for example, to combat The following plant parasitic nematodes are used: Meloidogyne species, Heterodera species, Ditylenchus species, Pratylenchus Species, Paratylenchus species, Anguina species, Helicotylenchus species, Tylenchorhynchus species, Radopholus species, Belonolaismus species, Trichodorus species, Longidorus species, Aphelenchoides species, Xiphinema species.

In addition to the properties mentioned above, the compounds of the formula I also have a favorable activity against representatives of the Thallophyta department when applied in very small amounts. Some of these compounds show bactericidal activity. But you are above all against fungi, especially against the following classes, orders or /. Species belonging to phytopathogenic fungi effective:

209840/1183

Oomycetes. such as Plasmodiophora species, Aphanomyces species,

Pythium species, Phytopthora species (Phytophthora tnfestans, Phytophthora cactorum), Plasmopara species (Plasmopara viticola), 3remia species (Brernia lactucae), Downy mildew a species (Peronospora tabacina), Pseudoperonospora species (Pseudoperonospora humuli).

Zyfro ^ iycetes, v / ie Rhizopus species.

Ascon; ycetes, vile Eurotiales, e.g. Aspergillus' species, Penicillium species (Penicillium digitatum, Penicillium italicutn), Taphrinales, e.g. Taphrina species (Taphrina deformane), Erysiphales, e.g. Erysiphe species (Erysiphe cichcrace-

arusn, Erysiphe grarainis, Podosphaera leucotricha), Sphaerothcca species (Sphacrotheca pannosa), Uncinula

Species (Uncinula necator),

Helotiales, vie Monilinia species (Monilinia [Sclerotiniaj fructicola, Monilinia laxa), Dlplocarpon species (Diplocarpon rosae), Pseudopeziza species,

Sphaeriales, such as Nectria species (Nectria gallißena), Ceratocystis species,

Pseudosphaeriales, such as Venturia species (Venturia inaequalis), Mycosphaerella species, Ophiobolus species (Ophiobolus graminus), Cochliobolus species [Helminthosporium] miyabeanus), Cercospora species (Cercospora beticola, Cercospora musae).

2098A0 / 1183

Basldiomycetes, such as Aphyllophorales, e.g. Pellicularia species (Pellicularia filamentora = [Rhizoctonia sonlani]), Uredinales, e.g. Puccinia species (Puccinia triticina), Uromyces species (Uromyces phaseoli), Hemileia species (Hemlleia vastatrix), Cronartium species Cronartium ribicola), Phraernidium species (Phraßmidium cubcorticiurn}, Gymnosporangium species.

Pcnteromycotos = (Fungi imperfecti)

e.g. Piricularia species (Piricularia oryzac), Cbri! iespora species. Thielaviopsis species, Clasterosporium species, Bctry tis species (Botrytis cinerea), CladoGporiutn-ArUcn, Alternaria species (Alternaria solani), Verticilliuni species (Vcrbiclllium albo-atrum), Phialophora species,

Melanconiales, e.g. Collctotrichusn species, Fusarium species (Fusarium oxysporum, Fusarium nivale) ^ Glocosporium species (Cloeocporium fructieenum),

Sphacropsidales, e.g. Septoria species (Septoria apicola).

Diplodia species (Diplodia natalensis), Mycelia sterilia, e.g. Sclerotium species (Sclcrotium.

rolfsii).

209840/1 183

The compounds of formula I also show a fungitoxic effect on fungi that the plants from Attack the soil and sometimes cause tracheomycosis, such as Fusarium cubense, Fusarium dianthi, Verticillium alboatrum and Phialophora einereceus.

The new active ingredients can also be used to treat seeds, fruits, tubers, etc. to protect against fungal infections for example through all kinds of smut fungi, such as

Ustilaginales, for example Ustilago species (Ustilage avenae), Tilletia species (Tilletia tritici), Urocystis and .Tuburcinia species
Phoma species (Phoma betae)

can be used.

Thanks to their biocidal properties, the

Compounds of the formula I for disinfecting and protecting various materials from infestation Bacteria and fungi. It proves to be particularly advantageous that the compounds of the formula I over Warm-blooded animals at the concentrations required for disinfection and material protection, none have toxic side effects.

In addition to the insecticides and acaricides mentioned, the compounds of the formula I can also be used with others Fungizidenj Fungistatika or bacteriostatika in different Mixing ratios are formulated, with compound mixtures having advantages over the individual components develop. For formulation with the active ingredients of the formula I are, for example: 209840/1183

Dodecylgu3nidiRace <ai (CCCINi) Pentschlornitrobenicl iGülSTOZESE) Penlachlic phenol (fCP)

2- (l-Mhyl-n-propyl) 4,5-diniirc? Hen) M-2-re! Hyl6rotoP3t (BtKAPACRYL)

2- (l-i'eU.yl-n-hcpiyl) -i, 6-dinilhrcrher.yicrolcnat (OIKCCA?). ·

?, 6-dichloro-i-nitrc3-iline (CICHLCS: ¹ ;) i ^^. C-Tstrachloro-lenzoquinone (1.0 (CKLCRAKIL)

Z.S-Dichlor-naphlhecrilnc :! (1.0 ÜÜCHLCSE) K- (lrichlorrethylthio) pr.ihal iaid (FCLP [T) K- (TrJchlorrethyl ^J ih: o) cyclchex-4-en-1,2-dicarboxicid (CAPIAS) K- (l _f l,?, 2-lctrachlcri {hyithio) cycIohcx-i-cn-l, 2-JicarboxiDid (CAPTATOL)

li-t'elhylsulfonal-fi-trichlororcihylthio-chJcra.niiin

K'-DUhlorfluorrethylihio-N-dkjthyl-S'-phenylsuIfaGid (OICHLCRfLUAUID) O-Acyl-S-Lnnyl-phenyl-III-thiophotphate

0,0-diethyI-S-benzyl-thiolptiosphate

Dlnatriuis-ethylene-l ^ -bis-dithiocarbaEat (WEAH) Zinli-äthylcn-i ^ -bis-dithiocarba.-at (ZIKEB) KanganOU-ethylene-V-bis-dithiccarbazat (KAfJEB) Tetrarethylthiuraidisjlfid (THIRAM)

l-oxy-3-acetyl-6-ethyl-cyclohexen- (5) dione- (2, O (OEHYDROACETIC ACID) 8 ~ Hydroxych'.nol in (8-CjJ. '. OLITiOL) i-DjF.ci'iylaaino-S- ^ cthyl-S-n-butyl-i-hydroxy-pyrinidine

Kcihyl-K-tenzicidazol ^ -yl-ii-fbutylcarbaroyDcarbanat (BES03YL)

2-Acthylasir.o-ß- !; ethyl-5n-buiyl- ^ - hydroxypyrinfdin i.a-Dlcyano-l ^ -dHhia-anthraquinone (DITHI ^ .O.'J) 2 - «- Th5azolyi) -bcn2ii.Jc! Azole

3,5-Dir.etSyHelrah / oro -), 3,5-thiadiazin-2-ihione (DAZOXlT) 2 _t 3-D i hydro-5-carbo / an i1i do-c-ce thy I-1,4-oxa thin

Pentachlorobenzy! Alcohol

The compounds of formula I can be used alone or together with suitable carriers and / or additives · Suitable carriers and 2 _USCN i _a g _SUBSTANCES can be solid or liquid and correspond to the substances common in formulation practice, such as natural or regenerated substances , Solvents, dispersants, wetting agents, adhesives, thickeners, binders and / or fertilizers.

For application, the compounds of formula (I) to dusts, emulsion concentrates, granulates, dispersions, sprays may be solutions or slurries on in a conventional formulation, are processed belongs in the application technology for general knowledge. There are also "cattle dips", ie cattle baths, and "spray"

2098AO / 1183

races ", i.e. spray courses in which aqueous preparations are used be to mention.

The agents according to the invention are produced in in a manner known per se by intimate mixing and / or grinding of active ingredients of the formula I with the suitable carriers, optionally with the addition of the active ingredients inert dispersants or solvents. The active ingredients can be used in the following processing forms are available and used:

solid processing forms: dusts, grit,

Granules, coated granules, impregnation granules and homogeneous granules

liquid processing forms:

a) dispersible in water

Active ingredient concentrates: wettable powder,

Pastes, emulsions;

b) Solutions

The active ingredients are mixed with solid carriers for the production of solid processing forms (dusts, grit). Carriers include kaolin, talc, bolus, loess, chalk, limestone, lime grit, ataclay, dolomite, diatomaceous earth, precipitated silica, alkaline earth silicates, sodium and potassium aluminum silicates (feldspar and mica), calcium and magnesium sulfates, magnesium oxide, ground plastics, Fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ground vegetable products such as grain flour, tree bark flour, wood flour, nutshell flour, cellulose powder, residues from plant extractions, activated charcoal, etc., each individually or as mixtures with one another. . . . _A *

209840/1183

Granules can be produced very easily by dissolving an active ingredient of the formula I in an organic solvent and applying the solution obtained in this way to a granulated mineral, for example attapulgite, SiO _? , Granicalcium, bentonite etc. and then the organic solvent evaporates again.

Polymer granules can also be produced by mixing the active ingredients of the formula I with polymerizable Compounds are mixed (urea / formaldehyde; dicyandiamide / Formaldehyde; Melamine / formaldehyde or others), after which a gentle polymerization is carried out, from which the active substances Remaining untouched, and with the granulation still occurring during the gel formation is made. It is cheaper to use finished, porous polymer granules (Urea / formaldehyde, polyacrylonitrile, polyester and others) with a specific surface and favorable predictability Adsorption / desorption ratio with the active ingredients, e.g. in the form of their solutions (in a low-boiling solvent) to impregnate and remove the solvent. Such polymer granules can be used in the form of micro-granules Bulky weight of preferably 300 g / liter to 600 g / liter as well be applied with the help of atomizers. The atomization can be done over large areas of crops with the help of Aircraft are carried.

Granules are also made by compacting the carrier material with the active ingredients and additives and then comminuting available.

These mixtures can also contain additives stabilizing the active ingredient and / or nonionic, anionic and cationic active substances Substances are added, for example the adhesive strength

209840/1183

improve the active ingredients on plants and plant parts (adhesive and adhesives) and / or ensure better wettability (wetting agents) and dispersibility (dispersants).

For example, the following substances are possible: olein-lime-Mi loop, cellulose derivatives (methyl cellulose, carboxymethyl cellulose), Hydroxyethylene glycol ethers of mono- and dialkylphenols with 5-15 Aethylenoxidresteii per molecule and 8-9 carbon atoms in the alkyl radical, ligninsulphonic acid, its alkali and alkaline earth salts, polyethylene glycol ether (Carbowax), Pettalkoholpolyglykoläther with 5-20 ethylene oxide residues per molecule and 8-18 carbon atoms in the fatty alcohol part, condensation products of ethylene oxide, propylene oxide, Polyvinylpyrrolidones, polyvinyl alcohols, condensation products of urea-formaldehyde and latex products.

Active ingredient concentrates dispersible in water, i.e. wettable powders, pastes and emulsion concentrates place . Represent means that can be diluted with water to any desired concentration. They consist of an active ingredient, a carrier, optionally additives stabilizing the active substance, surface-active substances and antifoams, and optionally Solvents.

The wettable powders and pastes are obtained by mixing and grinding the active ingredients with dispersants and pulverulent carriers in suitable devices until homogeneous. Suitable excipients are, for example, those mentioned above for the solid processing forms in question, in some cases, it is advantageous _$ mixtures of different carriers to use "The dispersants can be used, for example: condensation products of sulfonated

209840/1183

Naphthalene and sulfonated naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalene sulfonic acids with phenol and formaldehyde as well as alkali, ammonium and alkaline earth salts of lignosulphonic acid, further alkylarylsulphonates, alkali and alkaline earth metal salts of dibutylnaphthalenesulfonic acid, fatty alcohol sulfates, such as salts of sulfated hexadecanols, heptadecanols, octadecanols and salts of sulfated fatty alcohol glycol ethers, the sodium salt of QLe ylmethyltauride, ditertiary ethylene glycols, Dialkyldilaurylammonium chloride and fatty acid alkali and alkaline earth salts.

Silicones, for example, can be used as antifoam agents.

The active ingredients are mixed, ground, sieved and passed with the additives listed above in the same way as with the wettable powders the solid part has a grain size of 0.02 to 0.04 and at the pastes does not exceed 0.03 mm. For production of Emulsion concentrates and pastes are dispersants as listed in the previous sections, organic Solvent and water used. As solvents, for example, alcohols, benzene, xylenes, toluene, dimethyl sulfoxide and come Mineral oil fractions boiling in the range from 120 to 350 C are suitable. The solvents must be practically odorless, non-phytotoxic and inert to the active ingredients.

The agents according to the invention can also be used in the form of Solutions are applied. For this purpose, the active ingredient or several active ingredients of the general formula I are used in suitable organic: Solvents, solvent mixtures or dissolved in water,

209840/1183

As organic solvents, aliphatic and aromatic hydrocarbons, their chlorinated derivatives, alkyinaphthalenes, Mineral oils can be used alone or as a mixture with one another.

The content of active ingredient in the agents described above is between $ 0.1 and $ 95, it should be mentioned that the Application from the aircraft or by means of other suitable application devices, concentrations of up to $ 99.5 or even more pure Active ingredient can be used.

The active ingredients of the formula I can, for example, be formulated as follows:

Dust: For the production of a) 5 and b) 2 dusts the following substances are used:

a) 5 parts of active ingredient
95 parts of talc;

b) 2 parts of active ingredient

1 part of highly disperse silica, 97 parts of talc

The active ingredients are mixed and ground with the carrier substances.

Granulate: To produce a 5 $ granulate, the following Substances used:

- 5 parts of active ingredient

0.25 part of epichlorohydrin,
• Q> 3 parts cetyl polyglycol ether, 3.50 parts polyethylene glycol
91 parts of kaolin (grain size 0.3-0.8 mm).

D.vv Aktivcubstanr. is mixed with epichlorohydrin and dissolved with 6 parts of acetone, then polyethylene glycol and

2 0 9 8 U ü / 1 1 P 3

Ce ty I]) C lyglykc-j; 'tlK.r: ny .. · Kaolin sprayed on, and anr. Wettable powder: For the manufacture: ^

d) IO % \ cen spray powder

40 5 1

54 25

-Te sodium salt,
.: nsulfonic acid sodium salt,

':; O obtained solution is adjusted to ■ ■: ■' evaporated .- :; · .. ■ I, the acetone in vacuo. , -, ·.) 4Obigen, b) and c) 25 ^ i gen; - 'End components used:

Parts Do often make parts

Te j 3 Dibuty jin'ij) !: '];: Parts of Jo eecDäure; Te.i] c active ingredient

4.5 parts Ca] ei um-Li cn: ru ^ ulfonat, 1.9 Toi De Champagne-Kr · "·: de / Hydroxyethylcellulose-

Gemi scli (l: l) ,

3.5 parts of sodium dibutyl naphthalene sulfonate, 19.5 parts silica, 19.5 parts Champagne chalk, 28.1 parts of kaolin; 25 parts of active ingredient 2.5 parts of isooctylphenoxy-polyoxyethylene-ethanol, 1.7 parts champagne chalk / hydroxyethyl cellulose

Mixed (l: 1),

8.3 parts sodium aluminum silicate, 16.5 T-. ilc diatomaceous earth, 46 parts of kaolin; 10 parts active ingredient 3 parts mixture of the sodium salts of saturated

Fe 11a1koho1su1fa ten, 5 parts IJa phtha 1 insul fön acid formaldehyde condensate,

82

Share kaolin.

20Θ8Α0 / 1183

BATH ORIGINAL

The active ingredients are mixed in suitable mixers Aggregates are intimately mixed and ground on appropriate mills and rollers. You get wettable powder, which can be mixed with water

Allow suspensions to be diluted to any desired concentration. Emulsifiable concentrates: For the production of a) lO ^ igen and b) 25 / ^ igen emulsifiable concentrates are the following substances used:

a) IO parts active ingredient

3.4 parts epoxidized vegetable oil,

13 * 4 parts of a combination emulsifier, consisting of Pettalküho! .Polyglycol ether and alkylarylsulfonate calcium salt,

40 parts dimethylformamide, 4-3.2 parts xylene;

b) 25 parts of active ingredient

2.5 parts epoxidized vegetable oil,

10 parts of an alkylarylsulfonate fatty alcohol poly

glycol ether-Gernisches,
5 parts of dimethylformamide, 57.5 parts of xylene.

Emulsions of any desired concentration can be prepared from these concentrates by diluting them with water. Spray: For the production of a 5 ^ igen spray ..,. by means of the following ingredients are used: 5 parts active ingredient,
1 part epichlorohydrin,
94 parts of gasoline (Boiling Gronzen 16O - ⁰

\ 's

example 1

32.2 g of 3-amlnobenzotrifluoride are converted into the chlorohydrate in 200 ml of water with 60 ml of conc. Hydrochloric acid and diazotized in the usual way with 14 g of sodium nitrite in 60 ml of water.

Then stick material is passed through the solution for one hour at 0-2 C in order ^to remove any nitrous gases that may be present.

Then successively 50 ml of chlorobenzene, a solution of 44.8 g of Kai Inrrisa Lz der DLäthyld i thiophosphoric 'ire, 10.6 g of sodium carbonate in 100 ml of water and finally 0.2 part of Ki: pforpulv ^ r added, nasty Miochung is set to C or. · / Arm ι ,. for 2 hours.

After working up in a manner known per se, the active ingredient of the form L is obtained

CF

1.526

The following compounds manufactured:

CF_

'- οι?

° 1, 538

H 0 /!

CP.

((1Oc ₃ H ₇ C) ₂ -PS- ^ V

1.514

CF.

(Thu ₃ H ₇ O

P. 73

(CH

S ^CP 3

^lt521

rO

1,542

■ o

1.533

, 0

1.511

\H

, 0

1.527

0 9 8 4 0/1183

Example 2

insecticidal Frassf'ift-V.Mrku.nn;

Cotton plants and potato plants were treated with a 0.05 / 5% aqueous active substance emulsion (obtained from a 10 / o-strength emulsifiable concentrate) sprayed.

After the covering had dried on, the cotton plants were populated with Dlsdercus fasciatus nymphs and the potato plants with Colorado beetle larvae (Leptinotarsa decemlineata). The experiment was carried out at 24 ^° C. and 60 ° relative humidity.

The compounds according to Example 1 showed in the above Test a good insecticidal food poison effect against Disdercus fasciatus and Leptinotarsa decemlineata.

Example 3 Systemic insecticidal effect

To determine the systemic effect, rooted bean plants (Vicia fabae) are placed in an O, O, aqueous active ingredient solution (obtained from a 10 ^ emulsifiable concentrate). After 2 hours, aphids (Aphis fabae) were placed on the above-ground parts of the plant. The animals were protected from contact and gas effects by a special device. The experiment was carried out at 24 ° and 70% relative humidity.

209840/1183

In the above test, the compounds according to Example 1 showed a good systemic insecticidal action against Aphis fabae.

Example '■%
Acaricidal effect

a) Effect: on effort (Tet r anychus urticae)

Bean leaves were used to test the acaricidal effect., infested by adults, dormant stages and eggs of the red spider mite (Tetranychus urticae), with an O, O5 / 2-igen aqueous emulsion of the substance to be tested (made from a 25 / c-strength emulsifiable concentrate). The experiment was evaluated after 6 days. Strains of the red strains resistant to phosphoric acid esters were used as test animals Spider mite.

b) Effect on ticks ( Boophilus microplus) and their stages of development

For the following experiment, 10 adults each were ready to lay Ticks in aqueous drug emulsions for 5 minutes (Concentrations 100, 200, 400 and 800 ppm) immersed.

Then the ticks were kept at 27 ⁰ C and 80 ^ relative humidity. On 5 * 10 and 15. On the day of the egg laying was determined.

The compounds cc: NaGs Example 1 tested according to the tests a) and b) given above showed a good effect so-called Tetranychus urticae and Ütraphilus microplus.

209840/1183

'Example 5

Fungicidal effect

a) Action against Botirytis cinerea on Vicia faba

Three fully developed leaves of the same size from Vicia faba were placed in Petri dishes, which had been lined with moistened filter paper. were sprayed dripping wet with a sprayer. When the leaves were dry again, they were prepared fresh with a standardized spore suspension of the fungus (concentration: 100 ¹ OOO spores / ml) infected and maintained for 48 hours in a humid atmosphere at 20 C. After this time, they showed black, initially point-like spots that spread rapidly. The number and size of the infection sites served as an assessment wet rod for the effectiveness of the test substance.

b) Action against Erysiphs cichoracearun on Cucuils sntivus

Young Cucumis sativus plants were sprayed close to the spraying with a 0.05% suspension of the active ingredient formulated as a wettable powder and, after the spray coating had dried on, sprayed with a spore suspension of the fungus. After 8 Ta ^ η in a greenhouse at about 23 ° C, the degree of infection (percentage of he Hycelbelag coated sheet surface) on the infi :. species, treated balls compared to non-channeled, infected controls.

2098A0 / 1183

c) Action against Uroniyces appendix ulate s on Phaseolus yulgaris_

Phaseolus vulgaris plants in the Zv / egg-leaf stage were sprayed with a suspension of the substance formulated as a wettable powder to runoff point (concentration: 0.05% active substance). After the spray coating had dried on, the plants were infected with a fresh spore suspension of the bean grate and then kept in a humid chamber for one day and in a greenhouse at 20-22 ° C. for 12 days.

The number and size of the rust pustules were used as a benchmark for the effectiveness of the test substances.

d) Action against Phytophthora infestans on Solanum Lycope rsicum

S. Lycopexsicuni plants of the same cultivar and in the same Stage of development were with a broth of 0.05% active ingredient treated (made from the active substance processed into a wettable powder). After the spray coating has dried on the plants were sprayed dripping wet with a zoospore suspension of Ph. infestans. They then stayed for 6 days in a greenhouse at 18-2O ° C and high humidity (95-100%) and showed typical leaf spots after this time. Because of The number and size of the tested substance were assessed.

The compounds according to Example 1 show in the above Tests a) to d) fungicidal effect.

209840/1183

Example 6 Action against soil natodes

To test the action against soil nematodes, the active ingredients were in the given concentration in Root cell nematodes (Meloidogyne Avenaria) infected soil given and intimately mixed. Immediately afterwards tomato seedlings were placed in the soil prepared in this way in a test series planted and in a second series of experiments sown tomatoes after 8 days before the season.

The nematocidal effect was assessed for 28 days after planting or after sowing, the galls present on the roots are counted.

In this test, the active ingredients according to Example 1 showed a good effect against Meloidogyne Avenaria.

209840/1183

Claims (1)

Patent claims Compounds of the formula where R, and PU are each alkyl and X and Y are each. Oxygen · or sulfur mean. G. Compounds according to claim 1 of the formula wherein FU and FU are each C-j-C-, alkyl and X and Y are each oxygen or Mean sulfur. 3. Compounds according to claim 2 of the formula wherein R-, and R _{2 are} each C, -CU alkyl. 4. Compounds according to claim 2 of the formula 209840/1183 wherein R, and R "are each C-. -C ₇ . Mean alkyl. 5. A compound according to claim 4 of the formula '2 ^η 5 ^υ; 2 Compound according to claim 4 of the formula 3 ν, 2 A compound according to claim 4 of the formula A compound according to claim 3 of the formula (H) C ₃ H ₇ S A compound according to claim 3 of the formula (H) C ₃ H ₇ S 209840/1 183 10. Process for the preparation of compounds of the formula where R. and R are each alkyl and X and Y are each oxygen or sulfur mean, gekennzelohnet that you are connected to the formula PSM
/
E ₂ T lets act on a diazotized trifluoromethylaniline, where R ,, TL ·, Y and X have the meaning given above and M stands for a metaUatom. 11. Pesticides, which as the active component a compound of the formula R, and R ^ each denote alkyl and X and Y each denote oxygen or sulfur, and contain suitable carriers and / or other additives.
12. Use of compounds of the formula 209840/1183 wherein R-. and R is each alkyl and X and Y are each oxygen or sulfur mean to combat various animal and vegetable pests. 13. Use according to claim 12 for combating insects and representatives of the order Akarina. 14. Use according to claim 12 for combating phytopathogens Mushrooms. 15. Use according to claim 12 for combating plant parasites Nematodes. FO 3.35 WH / ps 209840/1183 ORIGINAL INSPECTED