DE2604225A1 - Fungicides for plant and inanimate organic materials - contg. S-phenyl-carbamoyl-methyl dithio-phosphate and thio-phosphonate derivs. - Google Patents

Fungicides for plant and inanimate organic materials - contg. S-phenyl-carbamoyl-methyl dithio-phosphate and thio-phosphonate derivs.

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Publication number
DE2604225A1
DE2604225A1 DE19762604225 DE2604225A DE2604225A1 DE 2604225 A1 DE2604225 A1 DE 2604225A1 DE 19762604225 DE19762604225 DE 19762604225 DE 2604225 A DE2604225 A DE 2604225A DE 2604225 A1 DE2604225 A1 DE 2604225A1
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DE
Germany
Prior art keywords
oc2h5
alkyl
och3
oc4h9
alkoxy
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Pending
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DE19762604225
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German (de)
Inventor
Gerhard Dipl Chem Dr Hroelein
Burkhard Sachse
Gerhard Dipl Chem Dr Salbeck
Hubert Dipl Chem D Schoenowsky
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Hoechst AG
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Hoechst AG
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Application filed by Hoechst AG filed Critical Hoechst AG
Priority to DE19762604225 priority Critical patent/DE2604225A1/en
Priority to NL7700930A priority patent/NL7700930A/en
Priority to BG035295A priority patent/BG27723A3/en
Priority to BG7942073A priority patent/BG28979A4/en
Priority to BG7742074A priority patent/BG28980A4/en
Priority to EG58/77A priority patent/EG12788A/en
Priority to TR19568A priority patent/TR19568A/en
Priority to GB4194/77A priority patent/GB1565894A/en
Priority to RO7789255A priority patent/RO70320A/en
Priority to NZ183238A priority patent/NZ183238A/en
Priority to AT64177A priority patent/AT355860B/en
Priority to LU76690A priority patent/LU76690A1/xx
Priority to CH125277A priority patent/CH631721A5/en
Priority to FI770368A priority patent/FI770368A/fi
Priority to PH19410A priority patent/PH12483A/en
Priority to IL51372A priority patent/IL51372A/en
Priority to BR7700642A priority patent/BR7700642A/en
Priority to IT19896/77A priority patent/IT1078001B/en
Priority to DD7700197194A priority patent/DD129105A5/en
Priority to US05/764,995 priority patent/US4140774A/en
Priority to DK45977A priority patent/DK149346C/en
Priority to JP52010342A priority patent/JPS6013039B2/en
Priority to IE226/77A priority patent/IE44595B1/en
Priority to YU00284/77A priority patent/YU28477A/en
Priority to CA271,007A priority patent/CA1088065A/en
Priority to FR7702989A priority patent/FR2340324A1/en
Priority to PT66151A priority patent/PT66151B/en
Priority to ZA770604A priority patent/ZA77604B/en
Priority to GR52705A priority patent/GR70331B/el
Priority to AU21907/77A priority patent/AU506483B2/en
Priority to BE174697A priority patent/BE851126A/en
Priority to OA56060A priority patent/OA05558A/en
Priority to CS77752A priority patent/CS199286B2/en
Priority to SE7701260A priority patent/SE427663B/en
Priority to MX775415U priority patent/MX4478E/en
Priority to AR266430A priority patent/AR219488A1/en
Publication of DE2604225A1 publication Critical patent/DE2604225A1/en
Priority to KE3127A priority patent/KE3127A/en
Priority to YU01899/82A priority patent/YU189982A/en
Priority to MY6/82A priority patent/MY8200006A/en
Pending legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6527—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07F9/6533—Six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/22—Amides of acids of phosphorus
    • C07F9/24—Esteramides
    • C07F9/2404—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/2408—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic of hydroxyalkyl compounds

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

New fungicidal agents contain an effective amt. of a cpd. of formula (I). In this formula, each R is H, halogen, 1-4C alkyl, 1-2C haloalkyl, 1-2C alkoxy, NO2, CN, SO2CH3, COOCH3 or SO2NH2; R1 is 1-6C alkyl; R2 is 1-6C alkyl, 1-6C alkoxy, 1-6C alkylamino, 3-6C alkenylamino or di(1-6C alkyl)amino; R3 is 1-2C alkyl or 1-6C alkoxy, R2 and R3 not both being alkyl; R4 is H or CH3; X is O or S; and n is 1, 2 or 3. Typical cpd. is S- N-(4-chlorophenyl)-N-isopropylcarbamoylmethyl -O,O-diethylphos- phate. (I) are fungicides (with a certain amount of systemic activity) active partic. against Ascomycetes (e.g. true mildew and Piricularia) and rusts. Apart from their use in plant protection, (I) can also be used as fungicides in inanimate organic substrates, e.g. paints, oils, leather, protein, paper and textiles. The phytotoxicity of (I) is low.

Description

Fungizide MittelFungicides

Gegenstand der Erfindung sind fungizide Mittel, die gekennzeichnet sind durch einen wirksamen Gehalt an einer Verbindung der allgemeinen Formel worin R = gleiche oder verschiedene Reste aus der Gruppe H, Halogen, (C1-C4)-Alkyl, (C1-C2)-Halogenalkyl, (C1-C2)-Alkoxy, NO2, CN, SO2CH3, COOCH3, S02NH2, R1 = (C1-C6)-Alkyl, R2 = (C1-C6)-Alkyl, (C1-C6)-Alkoxy, (C1-C6)-Alkylamino, (C3-C6)--Alkenylamino, Di-(C1-C6)-alkylamino R3 = (C1-C2)-Alkyl, (C1-C6)-Alkoxy, mit der Maßgabe, daß R2 und R3 nicht gleichzeitig Alkyl sind, R4= H oder Methyl, X = Sauerstoff oder Schwefel, und n = eine ganze Zahl von 1 - 3 ist.The invention relates to fungicidal agents which are characterized by an effective content of a compound of the general formula where R = identical or different radicals from the group H, halogen, (C1-C4) -alkyl, (C1-C2) -haloalkyl, (C1-C2) -alkoxy, NO2, CN, SO2CH3, COOCH3, SO2NH2, R1 = (C1-C6) -alkyl, R2 = (C1-C6) -alkyl, (C1-C6) -alkoxy, (C1-C6) -alkylamino, (C3-C6) -alkenylamino, di- (C1-C6) -alkylamino R3 = (C1-C2) -alkyl, (C1-C6) -alkoxy, with the proviso that R2 and R3 are not simultaneously alkyl, R4 = H or methyl, X = oxygen or sulfur, and n = a whole Number from 1 to 3 is.

Die Verbindungen der Formel I sind zum Teil bereits Gegenstand der US-PS 3 o57 774, US-PS 3 1o2 o19 und DT-AS 1 122 935 und darin als Insektizide und Akarizide bzw. Herbizide beschrieben. Es ist jedoch neu und überraschend, daß sie auch vorteilhafte fungizide Eigenschaften besitzen.Some of the compounds of the formula I are already the subject matter of US-PS 3,057,774, US-PS 3 1o2 o19 and DT-AS 1 122 935 and therein as insecticides and Acaricides and herbicides are described. It is new and surprising, however, that they also have advantageous fungicidal properties.

Bevorzugte Reste in den Verbindungen der allgemeinen Formel I sind: R = H, F, Cl, Br, (C1-C4)-Alkyl, CF3, NO2, OCH3, R1 = (C1-C4)-Alkyl, R2 = (C1-C4)-Alkyl, (C1-C4)-Alkoxy, (C1-C4)-Alkylamino, N-Allylamino und N,N-Dimethylamino R = (C1-C6)-Alkoxy 3 n = 1 oder 2 Ohne Anspruch auf Vollständigkeit sollen im folgenden einige Pilze genannt werden, gegen die diese Verbindungen wirksam sind: Erysiphe graminis (Weizenmehltau) Erysiphe cichoracearum (Gurkenmehltau) Puccinia triticina (Weizenbraunrost) Piricularia oryzae Die Verbindungen der Formel I werden nach an sich bekannten Methoden hergestellt, die in den weiter vorne genannten Schutzrechten beschrieben sind. Soweit sie darin nicht ausdrücklich ..erwähnt sind, lassen sie sich in analoger Weise unter Verwendung entsprechender Ausgangsstoffe gewinnen. Beispielsweise erhält man sie durch Umsetzung von Verbindungen der Formel II mit Phosphorverbindungen.der Formel III wobei jeweils einer der Reste R4 und R5 Halogen, insbesondere Chlor oder Brom, und der andere die SY-Gruppe bedeutet, in welcher Y Wasserstoff oder ein Metallkation darstellt, gegebenenfalls in Gegenwart eines säurebindenden Mittels.Preferred radicals in the compounds of general formula I are: R = H, F, Cl, Br, (C1-C4) -alkyl, CF3, NO2, OCH3, R1 = (C1-C4) -alkyl, R2 = (C1- C4) -alkyl, (C1-C4) -alkoxy, (C1-C4) -alkylamino, N-allylamino and N, N-dimethylamino R = (C1-C6) -alkoxy 3 n = 1 or 2 Without claiming to be exhaustive In the following some fungi are mentioned against which these compounds are effective: Erysiphe graminis (wheat powdery mildew) Erysiphe cichoracearum (cucumber powdery mildew) Puccinia triticina (wheat brown rust) Piricularia oryzae The compounds of formula I are prepared according to methods known per se, which are mentioned in the above Property rights are described. Unless they are expressly ... mentioned therein, they can be obtained in an analogous manner using appropriate starting materials. For example, they are obtained by reacting compounds of the formula II with phosphorus compounds of the formula III where in each case one of the radicals R4 and R5 is halogen, in particular chlorine or bromine, and the other is the SY group in which Y is hydrogen or a metal cation, optionally in the presence of an acid-binding agent.

Die Thioglykolsäureanilide gemäß Formel ii lassen sich nach literaturbekannten Methoden herstellen. Die Halogenphosphorverbindungen der Formel III sind bekannt und nach üblichen Methoden leicht zugänglich.The thioglycolic acid anilides according to formula ii can be according to the literature Establish methods. The halophosphorus compounds of the formula III are known and easily accessible by conventional methods.

Die Verbindungen der Formel I zeichnen sich durch gute fungizide Eigenschaften aus und können daher besonders zum Schutz von Pflanzen, vor allem in der Landwirtschaft, eingesetzt werden.The compounds of the formula I are distinguished by good fungicidal properties and can therefore be used to protect plants, especially in agriculture, can be used.

Besonders ausgeprägt ist ihre Wirkung gegen Ascomyceten (z. B.Their action against Ascomycetes (e.g.

echten Mehltau und Piricularia) sowie gegen Rostpilze. Da sie über eine gewisse systemische Wirksamkeit verfügen, können durch Behandlung des Saatguts oder des Bodens Pilzkrankheiten an der sich entwickelnden Pflanze unterdrückt werden Andererseits wirken die erfindungsgemäßen Mittel an toten organischen Substraten, so daß sie Substanzen, wie Farben, Öle, Leder, Eiweiß, Papier und Textilien, vor Pilzbefall schützen.powdery mildew and piricularia) as well as against rust fungi. Since they are over A certain systemic effectiveness can be achieved by treating the seed or the soil fungal diseases on the developing plant can be suppressed On the other hand, the agents according to the invention act on dead organic substrates, so that they contain substances such as paints, oils, leather, egg whites, paper and textiles Protect fungal infestation.

Hervorzuheben ist ihre geringe Phytotoxizität. Bei den im Pflanzenschutz üblichen Wirkstoffkonzentrationen treten keinerlei Pflanzenschäden auf.Their low phytotoxicity should be emphasized. For those in crop protection The usual concentrations of active substances do not cause any damage to the plants.

Für die Verwendung im Pflanzenschutz werden die Wirkstoffe der Formel I in Form üblicher Zubereitungen, z. B. als Spritzpulver, Stäubemittel, Emulsionskonzentrate oder Granulate und gegebenenfalls im Gemisch mit weiteren bioziden Wirkstoffen, insbesondere anderen Fungiziden, sowie Insektiziden, Akariziden oder Herbiziden eingesetzt.For use in crop protection, the active ingredients of the formula I in the form of customary preparations, e.g. B. as wettable powders, dusts, emulsion concentrates or granulates and possibly in a mixture with other biocidal active ingredients, in particular other fungicides, as well as insecticides, acaricides or herbicides used.

Die erfindungsgemäßen Mittel enthalten die Wirkstoffe der Formel I im allgemeinen zu 2 - 95 Gew.-%.The agents according to the invention contain the active ingredients of the formula I. generally from 2 to 95% by weight.

Benetzbare Pulver sind in Wasser gleichmäßig dispergierbare Präparate, die neben dem Wirkstoff außer einem Verdünnungs-oder Inertstoff noch Netzmittel, z. B. polyoxäthylierte Alkylphenole, polyoxäthylierte Oleyl- oder Stearylamine, hlkyl-oder Alkylphenyl-sulfonate und Dispergiermittel, z. B. ligninsulfonsaures Natrium, dibutylnaphthalinsulfonsures Natrium oder auch oleylmethyltaurinsaures Natrium enthalten.Wettable powders are preparations that can be uniformly dispersed in water, which in addition to the active ingredient besides a diluent or inert substance also wetting agents, z. B. polyoxyethylated alkylphenols, polyoxyethylated oleyl or stearyl amines, alkyl or alkylphenyl sulfonates and dispersants, e.g. B. ligninsulfonic acid Sodium, sodium dibutylnaphthalenesulfonic acid or oleylmethyltauric acid Contain sodium.

Emulgierbare Konzentrate werden durch Auflösen des Wirkstoffes in einem organischen Lösungsmittel, z. B. Butanol, Cyclohexanon, Dimethylformamid, Xylol oder auch höhersiedenden Aromaten erhalten.Emulsifiable concentrates are made by dissolving the active ingredient in an organic solvent, e.g. B. butanol, cyclohexanone, dimethylformamide, Get xylene or higher-boiling aromatics.

Um in Wasser gute Emulsionen zu erreichen, werden weiterhin Netzmittel aus der obengenannten Reihe zugesetzt.In order to achieve good emulsions in water, wetting agents are still used from the above series added.

Stäubemittel erhält man durch Vermahlen des Wirkstoffes mit fein verteilten, festen Stoffen, z. B. Talkum, natürlichen Tonen, wie Kaolin, Bentonit, Pyrophillit oder Diatomeenerde.Dust is obtained by grinding the active ingredient with finely divided, solid materials, e.g. B. talc, natural clays such as kaolin, bentonite, pyrophillite or diatomaceous earth.

Versprühbare Lösungen,- wie sie vielfach in Sprühdosen gehandelt werden, enthalten den Wirkstoff in einem organischen Lösungsmittel gelöst daneben befindet sich z. B. als Tribmittel ein Gemisch von Fluorchlorkohlenwasserstoffen.Sprayable solutions - as they are often traded in spray cans, contain the active ingredient dissolved in an organic solvent located next to it z. B. a mixture of chlorofluorocarbons as tributants.

Granulate können entweder durch Verdüsen des .Wirkstoffes auf adsorptionsfähiges, granuliertes Inertmaterial hergestellt werden oder durch Aufbringen von irkstoffkonzentraten mittels Klebemitteln, z.B. Polyvinylalkohol, polyacrylsaurem Natrium oder auch Mineralölen auf die Oberfläche von Trägerstoffen, wie Sand, Kaolinite, oder von granuliertem Inertmaterial.Granules can either be sprayed onto adsorptive, granulated inert material can be produced or by applying active ingredient concentrates by means of adhesives, e.g. polyvinyl alcohol, polyacrylic acid sodium or mineral oils on the surface of carrier materials such as sand, kaolinite, or granulated Inert material.

Auch können geeignete Wirkstoffe in der für die Herstellung von Düngemittelgranalien üblichen Weise, gewünschtenfalls in Mischung mit Düngemitteln, hergestellt ierden. Suitable active ingredients can also be used in the production of fertilizer granules in the usual way, if desired in a mixture with fertilizers.

Die Konzentrationen der Wirkstoffe in den handelsüblichen Formulierungen können verschieden sein.The concentrations of the active ingredients in the commercially available formulations can be different.

In benetzbaren Pulvern variiert die Wirkstoffkonzentration z.B. zwischen etwa 10 % und 95 ,, der Rest besteht aus den oben angegebenen Formulierungszusätzen. Bei emulgierbaren Konzentraten ist die Wirkstoffkonzentration etwa 10 % bis 80 %. Staubförmige Formulierungen enthalten meisten 5 - 20 % an Wirkstoff, verspri;hbare Lösungen etwa 2 - 20 . Bei Granulaten hängt der Wirkstoffgehalt z.T. davon ab, ob die wirksame Verbindung flüssig oder fest vorliegt und welche Granulierhilfsmittel, Füllstoffe usw. verwendet werden.In wettable powders, the active ingredient concentration varies e.g. between about 10% and 95%, the remainder consists of the formulation additives given above. In the case of emulsifiable concentrates, the active ingredient concentration is around 10% to 80%. Dust-like formulations usually contain 5 - 20% active ingredient, which can be sprayed Solutions around 2 - 20. In the case of granules, the active ingredient content depends partly on whether the active compound is liquid or solid and which granulating aids, Fillers, etc. can be used.

im Pflanzenschutz Zur Anwendvngt-.ferden die handelsüblichen Konzentrate gegebenenfalls in üblicher Weise verdünnt, z.B. bei benetzbaren Pulvern und emulgierbaren Konzentraten mittels Wasser. In crop protection, the commercially available concentrates are used if necessary diluted in the usual way, e.g. in the case of wettable powders and emulsifiable powders Concentrates using water.

Staubförmige und granulierte Zubereitungen sowie versprühbare Lösungen werden vor der Anwendung nicht mehr mit weiteren inerten Stoffen verdiinnt, Wäßrige Dispersionen der erfindungsgemäßen Mittel enthalten die Wirkstoffe im allgemeinen in Konzentrationen zwischen o,oo6 bis o,1 Gew.-%. Bei der Anwendung auf toten organischen Substraten im technischen Bereich kann die Wirkstoffkonzentration der fertigen Zubereitungen bis zu 1.o Gew.-% betragen.Dust-like and granulated preparations as well as sprayable solutions are no longer diluted with other inert substances before use, aqueous ones Dispersions of the agents according to the invention generally contain the active ingredients in concentrations between 0.06 to 0.1% by weight. When applying to dead organic Substrates in the technical field can be the concentration of active substances in the finished preparations up to 1.o wt .-%.

HERSTELLUNGSBEISPIELE Allgemeine Vorschrift Zu einer Lösung oder Suspension von 0,10-0,11 Mol eines Ammoniumsalzes einer Phosphorverbindung der Formel (III) (R5 = SNH4) in 200 ml Glykoldimethyläther gibt man bei Raumtemperatur unter Rühren 0,1 Mol eines Chloracetanilids der Formel (II) (R4 = C1).PREPARATION EXAMPLES General instructions For a solution or suspension from 0.10-0.11 mol of an ammonium salt of a phosphorus compound of the formula (III) (R5 = SNH4) in 200 ml of glycol dimethyl ether is added at room temperature with stirring 0.1 mol of a chloroacetanilide of the formula (II) (R4 = C1).

Man rührt ca. 3 - 5 Stunden bei 500C, saugt vom ausgefallenen Salz ab, verdünnt das Filtrat mit ca. 400 ml Benzol, wäscht die organische Phase gründlich mit Wasser und trocknet über Natriumsulfat.The mixture is stirred for about 3-5 hours at 50 ° C. and the precipitated salt is sucked off off, dilute the filtrate with approx. 400 ml of benzene, and wash the organic phase thoroughly with water and dry over sodium sulfate.

Nach dem Abdestillieren des Lösungsmittels hinterbleiben die Verfahrensprodukte als Oele, die zum Teil beim Antreiben kristallisieren.After the solvent has been distilled off, the process products remain as oils, some of which crystallize when driven.

Nach dem oben angegebenen Verfahren wurden die in der folgenden Tabelle zusamnengefaßten Verbindungen der Formel (I) gewonnen, deren Zusammensetzung durch Elementaran;Rlyse bestätigt wurde. Sie sind durch Brechungslndex oder Schmelzpunkt charakterisiert.Following the procedure given above, those in the following table Collected compounds of the formula (I) obtained, their composition by Elementaran; rlyse was confirmed. They are by refractive index or melting point characterized.

Tabelle Bsp. R n R1 R2 R3 X nD bzw. Fp. .1 2-F -CH(CH3)2 -OCH3 -OCH3 S nD23 1.5372 2 2-F -CH(CH3)2 -OC2H5 -OC2H5 S Fp. 41-45°C 3 2-F -CH(CH3)2 -OC3H7(n) -OC3H7(n) S nD34 1.5286 3 3-F -CH(CH3)3 -OC2H5 -OC2H5 S Fp. 50-56°C 4 3-F -CH(CH3)2 -OC3H7(n) -OC3H7(n) S nD34 1.5300 6 4-F -CH(CH3)2 -OCH3 -OCH3 S nD24 1.5433 7 4-F -CH(CHS )2 -OC2H5 -OC2H5 S Fp. 33-35°C 8 4-F -CH(CH3)2 -OC2H5 -OC2H5 O nD34 1.5072 9 4-F -CH(CH3)2 -OCH(CH3)2 -OCH(CH3)2 S Fp. 66-69°C 10 4-F -CH(CH3)3 -OC3H7(n) -OC5H7(n) S nD21 1.5224 11 4-F -CH(CH3)2 -OC4Hg (n) -OC4H9(n) S nD24 1.5610 12 2-Cl -CH3 -OC2H5 -OC5H5 S nD24 1.5473 13 2-Cl -CH3 -OC2H5 -OC2H5 O Fp. 66-69°C 14 3-Cl -CH3 -OC9H5 -OC2H5 S nD21 1.5639 15 3-Cl -CH3 -OC2H5 -OC2H5 O nD25 1.5323 16 4-C1 -CH(CH3)2 -OCH3 OCH3 5 nD24 1.5610 17 4-Cl -CH(CH3)2 -OC2H5 -OC2H5 S nD24 1.5530 18 4-Cl -CH(CH3)2 -OC2H5 -OC2H5 O nD25 1.5233 19 4-Cl -CH(CH3)2 -OC3H7(n) -OC3H7(n) S nD24 1.5416 20 4-Cl -C2H5 -OC2H5 -OC2H5 S nD25 1.5579 21 4-Cl -C2H5 -OC3H7(n) -OC5H5 S nD25 1.5457 22 4-Cl -C2H5 -OCH3 -OCH3 S nD25 1.5686 Tabelle (Fortsetzung) Bsp. R(n) R1 R2 R3 X nD bzw. Fp. 23 4-Cl -C2H5 -OC2H5 -OC2H5 O nD²³ 1.5330 24 4-Cl -C4H9(sek) -OCH3 -OCH3 S nD24 1.5586 25 4-Cl -C4H9(sek) -OC2H5 -OC2H5 S nD24 1.5457 26 4-Cl -C4H9(sek) -OC2H5 -OC2H5 O nD24 1.5198 27 4-Cl -C4H9(sek) -OC3H7(n) -OC3H7(n) S nD24 1.5386 28 4-Cl -CH3 -OC2H5 -OC2H5 S nD²³ 1.5609 29 4-Cl -CH3 -OC2H5 -OC2H5 O nD²¹ 1.5323 30 4-Br -CH(CH3)2 -OCH3 -OCH3 S Fp. 67-70°C 31 4-Br -CH(CH3)2 -OC2H5 -OC2H5 S Fp. 62-65°C 32 4-Br -CH(CH3)2 -OC2H5 -OC2H5 O Fp. 71-74°C 33 4-Br -CH(CH3)2 -OC3H7(n) -OC3H7(n) S Fp. 66-70°C 34 2,3-Cl -CH3 -OC2H5 -OC2H5 S nD²¹ 1.5767 35 2,3-Cl -CH3 -OC2H5 -OC2H5 O nD²¹ 1.5385 36 2,4-Cl -CH3 -OC2H5 -OC2H5 S nD27 1.5610 37 2,4-Cl -CH3 -OC2H5 -OC2H5 O nD24 1.5382 38 2,5-Cl -CH3 -OC2H5 -OC2H5 S nD27 1.5702 39 2,5-Cl -CH3 -OC2H5 -OC2H5 O nD27 1.5548 40 3,4-Cl -CH3 -OC2H5 -OC2H5 S nD²² 1.5700 41 3,4-Cl -CH3 -OC2H5 -OC2H5 O nD²³ 1.5432 42 3,5-Cl -CH3 -OC2H5 -OC2H5 S Fp. 62-65°C 43 3,5-Cl -CH3 -OC2H5 -OC2H5 O nD24 1.5410 44 2,4-F -CH(CH3)2 -OCH3 -OCH3 S nD²³ 1.5320 45 2,4-F -CH(CH3)2 -OC2H5 -OC2H5 S nD²³ 1.5270 46 2,4-F -CH(CH3)2 -OC3H7(n) -OC3H7(n) S nD²³ 1.5212 Tabelle (Fortsetzung) Bsp. R(n) R1 R2 R3 X nD bzw. Fp. 47 3-Cl, 4,6-F -CH(CH3)2 -OC2H5 -OC2H5 S nD²³ 1.5425 48 3-Cl, 4,6-F -CH(CH3)2 -OC3H7(n) -OC3H7(n) S nD²³ 1.5313 49 3-Cl, 2-F -CH(CH3)2 -OCH3 -OCH3 S nD24 1.5565 50 3-Cl, 2-F -CH(CH3)2 -OC2H5 -OC2H5 S nD²³ 1.5430 51 3-C1, 2-F -CH(CH3)2 -OC3H7(n) -OC3H7(n) S nD24 1.5378 52 3-Cl, 4,6-F -CH(CH3)2 -OC2H5 -OC2H5 S nD²³ 1.5397 53 3-Cl, 4,6-F -CH(CH3)2 -OC3H7(n) -OC3H7(n) S nD²³ 1.5322 54 2-NO2 -CH3 -OC2H5 -OC2H5 O nD²² 1.5380 55 3-NO2 -CH3 -OC2H5 -OC2H5 S nD²³ 1.5727 56 3-NO2 -CH3 -OC2H5 -OC2H5 O nD²³ 1.5466 57 3-NO2 -C2H5 -OC2H5 -OCz ° nD²³ 1.5443 58 3-NO2 -C4H9(n) -OC2H5 -OC2H5 S nD25 1.5680 59 3-NO2 -C4H9(sek) -OC2H5 -OC2H5 O nD26 1.5428 60 4-NO2 -CH3 -OC2H5 -OC2H5 S Fp. 48-53°C 61 4-NO2 -CH3 -OC2H5 -OC2H5 O Fp. 48-52°C 62 4-NO2 -CH3 -OCH3 -OCH3 S Fp. 55-62°C 63 3-CF3 -CH(CH3)2 -OCH3 -OCH3 S nD24 1.5197 64 3-CF3 -CH(CH3)2 -OC2H5 -OC2H5 S nD24 1.5126 65 3-CF3 -CH(CH3)2 -OC3H7(n) -OC3H7(n) S nD24 1.5084 66 3-CF3 -C4H9(sek) -OCH3 -OCH3 S nD24 1.5171 67 3-CF3 -C4H9(sek) -OC2H5 -OC2H5 S nD24 1.5112 68 3-CF3 -C4H9(sek) -OC2H5 -OC2H5 O nD²³ 1.4865 69 3-CF3 -C4H9(sek) -OC3H7(n) -OC3H7(n) S nD25 1.5058 70 3,5-CF3 -C4H9(sek) -OCH3 -OCH3 S Fp. 56-60°C Tabelle (Fortsetzung) Bsp. R(n) R1 R2 R3 X nD bzw. Fp. 71 3,5-CF3 -C4H9(sek) -OC2H5 -OC2H5 S nD24 1.4856 72 3,5-CF3 -C4H9(sek) -OC2H5 -OC2H5 O nD24 1.4630 73 3,5-CF3 -C4H9(sek) -OC3H7(n) -OC3H7(n) S nD24 1.4831 74 3-CF3; -C4H9(sek) -OC2H5 -OC2H5 S nD²¹ 1.5343 4-OC2H5 75 4-CN -CH3 -OC2H5 -OC2H5 O Fp. 49-51°C 76 4-CN -CH3 -OC2H5 -OC2H5 S Fp. 64-67°C 77 4-SO2-NH2 -CH(CH3)2 -OCH3 -OCH3 S nD27 1.5620 78 4-SO2-NH2 -CH(CH3)2 -OC2H5 -OC2H5 S Fp. 75-80°C 79 4-SO2-NH2 -CH(CH3)2 -OCH3 -OCH3 S Fp. 102-08°C 80 4-SO2-NH2 -CH(CH3)2 -OC2H5 -OC2H5 S Fp. 128-32°C 81 4-SO2-NH2 -CH(CH3)2 -OC2H5 -OC2H5 S Fp. 100-02°C 82 4-COOCH3 -CH(CH3)2 -OCH3 -OCH3 S Fp. 67-70°C 83 4-COOCH3 -CH(CH3)2 -OC2H5 -OC2H5 O nD²³ 1.5265 84 4-COOCH3 -CH(CH3)2 -OC2H5 -OC2H5 S nD²³ 1.5444 85 4-OCH3 -CH(CH3)2 -OCH3 -OCH3 S nD28 1.5551 86 4-OCH3 -CH(CH3)2 -OC2H5 -OC2H5 S nD27 1.5447 87 4-OCH3 -CH(CH3)2 -OC2H5 -OC2H5 O nD27 1.5192 88 89 H -C2H5 -OC2H5 -OC2H5 S Fp. 49-51°C 90 H -CH(CH3)2 -OC2H5 -OC2H5 S Fp. 47-49°C 91 4-CH3 -CH(CH3)2 -OCH3 -OCH3 S nD27 1.5536 92 4-CH3 -CH(CH3)2 -OC2H5 -OC2H5 S nD28 1.5401 93 4-CH3 -CH(CH3)2 -OC2H5 -OC2H5 O nD27 1.5145 Tabelle (Fortsetzung) Bsp. R(n) R1 R2 R3 X nD bzw. Fp. 94 2,6-C2H5 -CH(CH3)2 -OCH3 -OCH3 S Fp. 47-53°C 95 2,6-C2H5 -CH(CH3)2 -OC2H5 -OC2H5 S Fp. 47-55°C 96 2,6-C2H5 -CH(CH3)2 -OCH(CH3)2 -OCH(CH3)2 S nD²³ 1.5296 97 2,6-C2H5 -CH(CH3)2 -OC4H9(n) -OC4H9(n) S nD²³ 1.5271 98 2-CH(CH3)2 -CH(CH3)2 -OCH3 -OCH3 S Fp. 70-75°C 99 2-CH(CH3)2 -CH(CH3)2 -OC2H5 -OC2H5 S Fp. 45-48°C 100 2-CH(CH3)2 -CH(CH3)2 -OCH(CH3)2 -OCH(CH3)2 S Fp. 40-45°C 101 2-CH(CH3)2 -CH(CH3)2 -OC4H9(n) -OC4H9(n) S nD²³ 1.5294 102 4-CH(CH3)2 -CH(CH3)2 -OC2H5 -OC2H5 O nD25 1.5169 103 4-CH(CH3)2 -CH(CH3)2 -OC2H5 -OC2H5 S nD²³ 1.5412 104 4-C(CH3)3 -CH(CH3)2 -OCH3 -OCH3 S Fp. 47-53°C 105 4-C(CH3)3 -CH(CH3)2 -OC2H5 -OC2H5 S Fp. 47-51°C 106 4-C(CH3)3 -CH(CH3)2 -OCH(CH3)2 -OCH(CH3)2 S nD²³ 1.5250 107 4-C(CH3)3 -CH(CH3)2 -OC4H9(n) -OC4H9(n) S nD24 1.5231 108 4-F -CH(CH3)2 -CH3 -OCH3 S nD²³ 1.5565 109 4-F -CH(CH3)2 -CH3 -OC2H5 S nD²³ 1.5498 110 4-F -CH(CH3)2 -C2H5 -OC2H5 S nD24 1.5454 111 4-F -CH(CH3)2 -CH3 -OC4H9(i) S nD24 1.5393 112 4-F -CH(CH3)2 -C4H9(i) -OC4H9(i) S nD²³ 1.5282 113 4-F -CH(CH3)2 -CH3 -OC4H9(i) O nD²³ 1.5132 114 2-Cl -CH3 -CH3 -OC2H5 S nD24 1.5725 115 3-Cl -CH3 -CH3 -OC2H5 S Fp. 53-55°C 116 4-Cl -CH3 -CH3 -OC2H5 S nD²³ 1.5830 117 4-Cl -CH3 -CH3 -OC2H5 S nD25 1.5767 Tabelle (Fortsetzung) Bsp. R(n) R1 R2 R3 X nD bzw. Fp. 118 4-Cl -C2H5 -CH3 -OC4H9(i) O nD29 1.5313 119 4-Cl -C2H5 -C4H9(i) -OC2H5 S nD25 1.5610 120 4-Cl -CH(CH3)2 -CH3 -OC2H5 S nD²³ 1.5715 121 4-Cl -CH(CH3)2 -CH3 -OC4H9(i) O nD25 1.5255 122 4-C1 -CH(CH3)2 -CH3 -OC2H5 S nD26 1.5624 123 4-Cl -CH(CH3)2 -C4H9(i) -OC4H9(i) S nD26 1.5455 124 4-Cl -C2H5 -CH3 -OC4H9(i) S nD24 1.5630 125 4-Cl -C4H9(sek) -CH3 -OC2H5 S nD24 1.5610 126 4-Cl -C4H9(sek) -CH3 -OC4H9(i) S nD24 1.5530 127 4-Cl -C4H9(sek) -CH3 -OC4H9(i) O nD24 1.5271 128 4-Cl -C4H9(sek) -C4H9(n) -OC2H5 S nD24 1.5533 129 4-Br -CH(CH3)2 -CH3 -OC4H9(i) S nD28 1.5636 130 4-Br -CH(CH3)2 -CH3 -OC4H9(i) S nD²³ 1.5783 131 4-Br -CH(CH3)z -CH3 -OC4H9(i) O nD²³ 1.5400 132 4-Br -CH(CH3)2 -C4H9(n) -OC2H5 S nD24 1.5676 133 2,3-Cl -CH3 -CH3 -OC2H5 S nD²¹ 1.6012 134 2,4-Cl -CH3 -CH3 -OC2H5 S nD24 1.5902 135 2,5-Cl -CH3 -CH3 -OC2H5 S nD27 1.6003 136 3,4-Cl -CH3 -CH3 -OC2H5 S Fp. 94°C 137 3,5-C1 -CH3 -CH3 -OC2H5 S Fp. 84-860C 138 3-CF3 -CH(CH3)2 -CH3 -OC2H5 S nD²² 1.5228 139 3-CF3 -CH(CH3)2 -CH3 -OC4H9(i) O nD25 1.4890 140 3-CF3 -CH(CH3)2 -CH3 -OC4H9(i) S nD²² 1.5145 141 3-CF3 -C4H9(sek) -CH3 -OC2H5 S nD24 1.5200 Tabelle (Fortsetzung) Bsp. R(n) R1 R2 R3 X nD bzw. Fp. 142 3-CF3 -C4H9(sek) -CH3 -OC4H9(i) O nD25 1.4910 143 3-CF3 -C4H9(sek) -CH3 -OC4H9(i) S nD25 1.5135 144 3-CF3 -C4H9(sek) -C4H9(i) -OC2H5 S nD24 1.5151 145 4-CN -CH3 -CH3 -OC2H5 S Fp. 80-830C 146 2-NO2 -CH3 -CH3 -OC2H5 S nD²³ 1.5882 147 3-NO2 -CH3 -CH3 -OC2H5 S nD25 1.5914 148 4-NO2 -C3H5 -CH3 -OC2H5 S Fp. 65-68°C 149 4-NO2 -CH(CH3)2 -CH3 -OC2H5 S Fp. 67-73°C 150 4-NO2 -C4H9(n) -CH3 -OC2H5 S nD25 1.5855 151 4-SO2-NH3 -CH(CH3)2 -CH3 -OC2H5 S nD27 1.5660 152 4-SO2-NH3 -CH(CH3)2 -CH3 -OC4H9(i) O Fp. 98-105°C 153 4-OCH3 -CH(CH3)2 -CH3 -OC2H5 S nD27 1.5592 154 4-OCH3 -CH(CH3)2 -CH3 -OC4H9(i) S nD27 1.5482 155 4-OCH3 -CH(CH3)2 -CH3 -OC4H9(i) O nD24 1.5262 156 4-CH3 -CH(CH3)2 -CH3 -OC2H5 S nD27 1.5453 157 4-CH3 -CH(CH3)2 -CH3 -OC4H9(i) S nD26 1.5566 158 2-CH(CH3)2 -CH(CH3)2 -CH3 -OCH3 S nD25 1.5566 159 2-CH(CH3)2 -CH(CH3)2 -CH3 -OC2H5 S Fp. 64-66°C 160 2-CH(CH3)2 -CH(CH3)2 -CH3 -OC4H9(i) O nD²³ 1.5223 161 2-CH(CH3)2 -CH(CH3)2 -CH3 -OC4H9(i) S nD²³ 1.5420 162 4-CH(CH3)2 -CH(CH3)2 -CH3 -OC2H5 S nD25 1.5542 163 4-C(CH3 )3 -CH(CH3s )2 -CH3 -OC2H5 s Fp. 54-590C 164 4-CH(CH3)2 -CH(CH3)2 -CH3 -OC4H9(i) S Fp. 64-73°C 165 H -CH(CH3)2 -CH3 -OC2H5 O Fp. 67-68°C Tabelle (Fortsetzung) Bsp. R(n) R1 R2 R3 X nD bzw. Fp 166 4-F -CH(CH3)2 -N(CH3)2 -OC2H5 O nD23 1.5192 167 2-Cl -CH3 -NHCH3 -OC2H5 O nD24 1.5534 168 2-Cl -CH3 -NHCH(CH3)2 -OC2H5 O nD24 1.5473 169 2-Cl -CH3 -NHCH2 CH=CH2 -OC2H5 O nD24 1.5513 170 2-Cl -CH3 -NH-C4H9 (n) -OC2H5 O nD24 1.5583 171 3-Cl -CH3 -NHCH3 -OC2H5 O nD24 1.5548 172 3-Cl -CH3 -NHCH(CH3)2 -OC2H5 O nD24 1.5388 173 3-Cl -CH3 -NHCH2 CH=CH2 -OC2H5 O nD24 1.5546 174 3-Cl -CH3 -NH-C4H9 (n) -OC2H5 O nD24 1.5410 175 4-Cl -CH3 -NHCH3 -OC2H5 O - 176 4-Cl -CH3 -NHCH(CH3)2 -OC2H5 O nD24 1.5413 177 4-Cl -C2H5 -N(CH3)2 -OC2H5 O nD28 1.5403 178 4-Cl -C4H9(sek) -N(CH3)2 -OC2H5 O nD24 1.5329 179 4-Cl -C4H9(sek) -NHCH(CH3)2 -OC2H5 O nD24 1.5316 180 4-Br -CH(CH3)2 -N(CH3)2 -OC2H5 O nD24 1.5465 181 4-Br -CH(CH3)2 -NHCH(CH3)2 -OC2H5 O nD24 1.5412 182 2,3-Cl -CH3 -NHCH3 -OC2H5 O nD24 1.5585 183 2,3-Cl -CH3 -NHCH(CH3)2 -OC2H5 O nD24 1.5452 184 2,4-Cl -CH3 -NHCH3 -OC2H5 O nD24 1.5604 185 2,4-Cl -CH3 -NHCH(CH3)2 -OC2H5 O nD24 1.5405 186 2,4-Cl -CH3 -NHCH2 CH=CH2 -OC2H5 O nD24 1.5542 187 2,4-Cl -CH3 -NH-C4H9 (n) -OC2H5 O nD24 1.5447 188 2,5-Cl -CH3 -NHCH3 -OC2H5 O nD24 1.5645 189 2,5-Cl -CH3 -NHCH(CH3)2 -OC2H5 O nD24 1.5502 Tabelle (Fortsetzung) Bsp. R(n) R1 R2 R3 X nD bzw. Fp 190 2,5-Cl -CH3 -NHCH2CH=CH2 -OC2H5 O nD24 1.5597 191 2,5-Cl -CH3 -NH-C4H9 (n) -OC2H5 O nD24 1.5474 192 3,4-C1 -CH3 -NH-CH3 -OC2H5 O nD24 1.5620 193 3,4-Cl -CH3 -NHCH(CH3)2 -OC2H5 O nD24 1.5451 194 3,4-Cl -CH3 -NH-C4H9 (n) -OC2H5 O nD24 1.5495 195 4-C(OH)2 -CH(CH3)2 -NH-CH3 -OC2H5 O nD24 1.5226 196 4-C(OH)2 -CH(CH3)2 -NHCH(CH3)2 -OC2H5 O nD24 1.5170 197 3-Cl -CH(CH3)2 -NH-CH3 -OC2H5 O nD24 1.4980 198 3-Cl -CH(CH3)2 -N(CH3)2 -OC2H5 O nD24 1.4835 199 3-Cl -CH(CH3)2 -NHCH(CH3)2 -OC2H5 O nD24 1.4953 200 3-Cl -C4H9(sek) -NH-CH3 -OC2H5 O nD24 1,4994 201 3-Cl -C4H9(sek) -N(CH3)2 -OC2H5 O nD24 1.4930 202 3-Cl -C4H9(sek) -NHCH(CH3)2 -OC2H5 O nD28 1.4953 203 3-Cl -C4H9(sek) -NHCH2 CH=CH2 -OC2H5 O nD24 1.5047 204 H -CH(CH3)2 -NH-C3H7 (n) -C2H5 S Fp. 76-78°C 205 4-Cl -CH(CH3)2 -N(CH3)2 -OCH5 O - Bsp. R(n) R1 R2 R3 X nD bzw. Fp 206 4-F -CH(CH3)2 -C2H5 -OC2H5 S nD24 1.5254 207 4-F -CH(CH3)2 -C3H7 (n) -OC5H7 (n) S nD24 1.5208 FO.Z5MULIERUNGSBEISPIELE Beispiel A: Ein in Wasser leicht dispergierbares benetzbares Pulver wird erhalten, indem man 25 Gewichtsteile Dithiophosphorsäure-S [N-(4-chlorphenyl)-N-isopropyl-carbamoylmethyl]-O,O-diäthylester als Wirkstoff, 64 Gewichtsteile kaolinhaltigen Quarz als Inertstoff, 10 Gewichtsteile ligninsulfonsaures Kalium und 1 Gewichtsteil oleylmethyltaurinsaures Natrium als Netz-und Dispergiermittel mischt und in einer Stiftmühle mahlt.Tabel Ex. R n R1 R2 R3 X nD or Fp. .1 2-F -CH (CH3) 2 -OCH3 -OCH3 S nD23 1.5372 2 2-F -CH (CH3) 2 -OC2H5 -OC2H5 S m.p. 41-45 ° C 3 2-F -CH (CH3) 2 -OC3H7 (n) -OC3H7 (n) S nD34 1.5286 3 3-F -CH (CH3) 3 -OC2H5 -OC2H5 S m.p. 50-56 ° C 4 3-F -CH (CH3) 2 -OC3H7 (n) -OC3H7 (n) S nD34 1.5300 6 4-F -CH (CH3) 2 -OCH3 -OCH3 S nD24 1.5433 7 4-F -CH (CHS) 2 -OC2H5 -OC2H5 S m.p. 33-35 ° C 8 4-F -CH (CH3) 2 -OC2H5 -OC2H5 O nD34 1.5072 9 4-F -CH (CH3) 2 -OCH (CH3) 2 -OCH (CH3) 2 S M.p. 66-69 ° C 10 4-F -CH (CH3) 3 -OC3H7 (n) -OC5H7 (n) S nD21 1.5224 11 4-F -CH (CH3) 2 -OC4Hg (n) -OC4H9 (n) S nD24 1.5610 12 2-Cl -CH3 -OC2H5 -OC5H5 S nD24 1.5473 13 2-Cl -CH3 -OC2H5 -OC2H5 O m.p. 66-69 ° C 14 3-Cl -CH3 -OC9H5 -OC2H5 S nD21 1.5639 15 3-Cl -CH3 -OC2H5 -OC2H5 O nD25 1.5323 16 4-C1 -CH (CH3) 2 -OCH3 OCH3 5 nD24 1.5610 17 4-Cl -CH (CH3) 2 -OC2H5 -OC2H5 S nD24 1.5530 18 4-Cl -CH (CH3) 2 -OC2H5 -OC2H5 O nD25 1.5233 19 4-Cl -CH (CH3) 2 -OC3H7 (n) -OC3H7 (n) S nD24 1.5416 20 4-Cl -C2H5 -OC2H5 -OC2H5 S nD25 1.5579 21 4-Cl -C2H5 -OC3H7 (n) -OC5H5 S nD25 1.5457 22 4-Cl -C2H5 -OCH3 -OCH3 S nD25 1.5686 Table (continued) Ex. R (n) R1 R2 R3 X nD or Fp. 23 4-Cl -C2H5 -OC2H5 -OC2H5 O nD23 1.5330 24 4-Cl -C4H9 (sec) -OCH3 -OCH3 S nD24 1.5586 25 4-Cl -C4H9 (sec) -OC2H5 -OC2H5 S nD24 1.5457 26 4-Cl -C4H9 (sec) -OC2H5 -OC2H5 O nD24 1.5198 27 4-Cl -C4H9 (sec) -OC3H7 (n) -OC3H7 (n) S nD24 1.5386 28 4-Cl -CH3 -OC2H5 -OC2H5 S nD23 1.5609 29 4-Cl -CH3 -OC2H5 -OC2H5 O nD21 1.5323 30 4-Br -CH (CH3) 2 -OCH3 -OCH3 S m.p. 67-70 ° C 31 4-Br -CH (CH3) 2 -OC2H5 -OC2H5 S m.p. 62-65 ° C 32 4-Br -CH (CH3) 2 -OC2H5 -OC2H5 O m.p. 71-74 ° C 33 4-Br -CH (CH3) 2 -OC3H7 (n) -OC3H7 (n) S m.p. 66-70 ° C 34 2,3-Cl -CH3 -OC2H5 -OC2H5 S nD21 1.5767 35 2,3-Cl -CH3 -OC2H5 -OC2H5 O nD21 1.5385 36 2,4-Cl -CH3 -OC2H5 -OC2H5 S nD27 1.5610 37 2,4-Cl -CH3 -OC2H5 -OC2H5 O nD24 1.5382 38 2,5-Cl -CH3 -OC2H5 -OC2H5 S nD27 1.5702 39 2,5-Cl -CH3 -OC2H5 -OC2H5 O nD27 1.5548 40 3,4-Cl -CH3 -OC2H5 -OC2H5 S nD²² 1.5700 41 3,4-Cl -CH3 -OC2H5 -OC2H5 O nD23 1.5432 42 3,5-Cl -CH3 -OC2H5 -OC2H5 S m.p. 62-65 ° C 43 3,5-Cl -CH3 -OC2H5 -OC2H5 O nD24 1.5410 44 2,4-F -CH (CH3) 2 -OCH3 -OCH3 S nD23 1.5320 45 2,4-F -CH (CH3) 2 -OC2H5 -OC2H5 S nD23 1.5270 46 2,4-F -CH (CH3) 2 -OC3H7 (n) -OC3H7 (n) S nD23 1.5212 Table (continued) Ex. R (n) R1 R2 R3 X nD or Fp. 47 3-Cl, 4,6-F-CH (CH3) 2 -OC2H5 -OC2H5 S nD23 1.5425 48 3-Cl, 4,6-F -CH (CH3) 2 -OC3H7 (n) -OC3H7 (n) S nD23 1.5313 49 3-Cl, 2-F-CH (CH3) 2 -OCH3 -OCH3 S nD24 1.5565 50 3-Cl, 2-F-CH (CH3) 2 -OC2H5 -OC2H5 S nD23 1.5430 51 3-C1, 2-F-CH (CH3) 2 -OC3H7 (n) -OC3H7 (n) S nD24 1.5378 52 3-Cl, 4,6-F-CH (CH3) 2 -OC2H5 -OC2H5 S nD23 1.5397 53 3-Cl, 4,6-F -CH (CH3) 2 -OC3H7 (n) -OC3H7 (n) S nD23 1.5322 54 2-NO2 -CH3 -OC2H5 -OC2H5 O nD²² 1.5380 55 3-NO2 -CH3 -OC2H5 -OC2H5 S nD²³ 1.5727 56 3-NO2 -CH3 -OC2H5 -OC2H5 O nD23 1.5466 57 3-NO2 -C2H5 -OC2H5 -OCz ° nD²³ 1.5443 58 3-NO2 -C4H9 (n) -OC2H5 -OC2H5 S nD25 1.5680 59 3-NO2 -C4H9 (sec) -OC2H5 -OC2H5 O nD26 1.5428 60 4-NO2 -CH3 -OC2H5 -OC2H5 S m.p. 48-53 ° C 61 4-NO2 -CH3 -OC2H5 -OC2H5 O m.p. 48-52 ° C 62 4-NO2 -CH3 -OCH3 -OCH3 S m.p. 55-62 ° C 63 3-CF3 -CH (CH3) 2 -OCH3 -OCH3 S nD24 1.5197 64 3-CF3 -CH (CH3) 2 -OC2H5 -OC2H5 S nD24 1.5126 65 3-CF3 -CH (CH3) 2 -OC3H7 (n) -OC3H7 (n) S nD24 1.5084 66 3-CF3 -C4H9 (sec) -OCH3 -OCH3 S nD24 1.5171 67 3-CF3 -C4H9 (sec) -OC2H5 -OC2H5 S nD24 1.5112 68 3-CF3 -C4H9 (sec) -OC2H5 -OC2H5 O nD23 1.4865 69 3-CF3 -C4H9 (sec) -OC3H7 (n) -OC3H7 (n) S nD25 1.5058 70 3,5-CF3 -C4H9 (sec) -OCH3 -OCH3 S m.p. 56-60 ° C Table (continued) Ex. R (n) R1 R2 R3 X nD or Fp. 71 3,5-CF3 -C4H9 (sec) -OC2H5 -OC2H5 S nD24 1.4856 72 3,5-CF3 -C4H9 (sec) -OC2H5 -OC2H5 O nD24 1.4630 73 3,5-CF3 -C4H9 (sec) -OC3H7 (n) -OC3H7 (n) S nD24 1.4831 74 3-CF3; -C4H9 (sec) -OC2H5 -OC2H5 S nD21 1.5343 4-OC2H5 75 4-CN-CH3 -OC2H5 -OC2H5 O m.p. 49-51 ° C 76 4-CN -CH3 -OC2H5 -OC2H5 S m.p. 64-67 ° C 77 4-SO2-NH2 -CH (CH3) 2 -OCH3 -OCH3 S nD27 1.5620 78 4-SO2-NH2 -CH (CH3) 2 -OC2H5 -OC2H5 S m.p. 75-80 ° C 79 4-SO2-NH2 -CH (CH3) 2 -OCH3 -OCH3 S M.p. 102-08 ° C 80 4-SO2-NH2 -CH (CH3) 2 -OC2H5 -OC2H5 S M.p. 128-32 ° C 81 4-SO2-NH2 -CH (CH3) 2 -OC2H5 -OC2H5 S m.p. 100-02 ° C 82 4-COOCH3 -CH (CH3) 2 -OCH3 -OCH3 S M.p. 67-70 ° C 83 4-COOCH3 -CH (CH3) 2 -OC2H5 -OC2H5 O nD23 1.5265 84 4-COOCH3 -CH (CH3) 2 -OC2H5 -OC2H5 S nD23 1.5444 85 4-OCH3 -CH (CH3) 2 -OCH3 -OCH3 S nD28 1.5551 86 4-OCH3 -CH (CH3) 2 -OC2H5 -OC2H5 S nD27 1.5447 87 4-OCH3 -CH (CH3) 2 -OC2H5 -OC2H5 O nD27 1.5192 88 89 H -C2H5 -OC2H5 -OC2H5 S m.p. 49-51 ° C 90 H -CH (CH3) 2 -OC2H5 -OC2H5 S m.p. 47-49 ° C 91 4-CH3 -CH (CH3) 2 -OCH3 -OCH3 S nD27 1.5536 92 4-CH3 -CH (CH3) 2 -OC2H5 -OC2H5 S nD28 1.5401 93 4-CH3 -CH (CH3) 2 -OC2H5 -OC2H5 O nD27 1.5145 Table (continued) Ex. R (n) R1 R2 R3 X nD or Fp. 94 2,6-C2H5-CH (CH3) 2 -OCH3 -OCH3 S M.p. 47-53 ° C 95 2,6-C2H5-CH (CH3) 2 -OC2H5 -OC2H5 S m.p. 47-55 ° C 96 2,6-C2H5 -CH (CH3) 2 -OCH (CH3) 2 -OCH (CH3) 2 S nD23 1.5296 97 2,6-C2H5 -CH (CH3) 2 -OC4H9 (n) -OC4H9 (n) S nD23 1.5271 98 2-CH (CH3) 2 -CH (CH3) 2 -OCH3 -OCH3 S m.p. 70-75 ° C 99 2-CH (CH3) 2 -CH (CH3) 2 -OC2H5 -OC2H5 S m.p. 45-48 ° C 100 2-CH (CH3) 2 -CH (CH3) 2 -OCH (CH3) 2 -OCH (CH3) 2 S M.p. 40-45 ° C 101 2-CH (CH3) 2 -CH (CH3) 2 -OC4H9 (n) -OC4H9 (n) S nD23 1.5294 102 4-CH (CH3) 2 -CH (CH3) 2 -OC2H5 -OC2H5 O nD25 1.5169 103 4-CH (CH3) 2 -CH (CH3) 2 -OC2H5 -OC2H5 S nD23 1.5412 104 4-C (CH3) 3 -CH (CH3) 2 -OCH3 -OCH3 S M.p. 47-53 ° C 105 4-C (CH3) 3 -CH (CH3) 2 -OC2H5 -OC2H5 S Mp 47-51 ° C 106 4-C (CH3) 3 -CH (CH3) 2 -OCH (CH3) 2 -OCH (CH3) 2 S nD 23 1.5250 107 4-C (CH3) 3 -CH (CH3) 2 -OC4H9 (n) -OC4H9 (n) S nD24 1.5231 108 4-F -CH (CH3) 2 -CH3 -OCH3 S nD23 1.5565 109 4-F -CH (CH3) 2 -CH3 -OC2H5 S nD23 1.5498 110 4-F -CH (CH3) 2 -C2H5 -OC2H5 S nD24 1.5454 111 4-F -CH (CH3) 2 -CH3 -OC4H9 (i) S nD24 1.5393 112 4-F -CH (CH3) 2 -C4H9 (i) -OC4H9 (i) S nD23 1.5282 113 4-F -CH (CH3) 2 -CH3 -OC4H9 (i) O nD 23 1.5132 114 2-Cl -CH3 -CH3 -OC2H5 S nD24 1.5725 115 3-Cl -CH3 -CH3 -OC2H5 S m.p. 53-55 ° C 116 4-Cl -CH3 -CH3 -OC2H5 S nD23 1.5830 117 4-Cl -CH3 -CH3 -OC2H5 S nD25 1.5767 Table (continued) Ex. R (n) R1 R2 R3 X nD or Fp. 118 4-Cl -C2H5 -CH3 -OC4H9 (i) O nD29 1.5313 119 4-Cl -C2H5 -C4H9 (i) -OC2H5 S nD25 1.5610 120 4-Cl -CH (CH3) 2 -CH3 -OC2H5 S nD23 1.5715 121 4-Cl -CH (CH3) 2 -CH3 -OC4H9 (i) O nD25 1.5255 122 4-C1-CH (CH3) 2 -CH3 -OC2H5 S nD26 1.5624 123 4-Cl -CH (CH3) 2 -C4H9 (i) -OC4H9 (i) S nD26 1.5455 124 4-Cl -C2H5 -CH3 -OC4H9 (i) S nD24 1.5630 125 4-Cl -C4H9 (sec) -CH3 -OC2H5 S nD24 1.5610 126 4-Cl -C4H9 (sec) -CH3 -OC4H9 (i) S nD24 1.5530 127 4-Cl -C4H9 (sec) -CH3 -OC4H9 (i) O nD24 1.5271 128 4-Cl -C4H9 (sec) -C4H9 (n) -OC2H5 S nD24 1.5533 129 4-Br -CH (CH3) 2 -CH3 -OC4H9 (i) S nD28 1.5636 130 4-Br -CH (CH3) 2 -CH3 -OC4H9 (i) S nD 23 1.5783 131 4-Br -CH (CH3) z -CH3 -OC4H9 (i) O nD 23 1.5400 132 4-Br -CH (CH3) 2 -C4H9 (n) -OC2H5 S nD24 1.5676 133 2,3-Cl -CH3 -CH3 -OC2H5 S nD21 1.6012 134 2,4-Cl -CH3 -CH3 -OC2H5 S nD24 1.5902 135 2,5-Cl -CH3 -CH3 -OC2H5 S nD27 1.6003 136 3,4-Cl -CH3 -CH3 -OC2H5 S M.p. 94 ° C 137 3,5-C1-CH3 -CH3 -OC2H5 S m.p. 84-860C 138 3-CF3 -CH (CH3) 2 -CH3 -OC2H5 S nD²² 1.5228 139 3-CF3 -CH (CH3) 2 -CH3 -OC4H9 (i) O nD25 1.4890 140 3-CF3 -CH (CH3) 2 -CH3 -OC4H9 (i) S nD22 1.5145 141 3-CF3 -C4H9 (sec) -CH3 -OC2H5 S nD24 1.5200 Table (continued) Ex. R (n) R1 R2 R3 X nD or Fp. 142 3-CF3 -C4H9 (sec) -CH3 -OC4H9 (i) O nD25 1.4910 143 3-CF3 -C4H9 (sec) -CH3 -OC4H9 (i) S nD25 1.5135 144 3-CF3 -C4H9 (sec) -C4H9 (i) -OC2H5 S nD24 1.5151 145 4-CN-CH3 -CH3 -OC2H5 S m.p. 80-830C 146 2-NO2 -CH3 -CH3 -OC2H5 S nD23 1.5882 147 3-NO2 -CH3 -CH3 -OC2H5 S nD25 1.5914 148 4-NO2 -C3H5 -CH3 -OC2H5 S m.p. 65-68 ° C 149 4-NO2 -CH (CH3) 2 -CH3 -OC2H5 S m.p. 67-73 ° C 150 4-NO2 -C4H9 (n) -CH3 -OC2H5 S nD25 1.5855 151 4-SO2-NH3 -CH (CH3) 2 -CH3 -OC2H5 S nD27 1.5660 152 4-SO2-NH3 -CH (CH3) 2 -CH3 -OC4H9 (i) O M.p. 98-105 ° C 153 4-OCH3 -CH (CH3) 2 -CH3 -OC2H5 S nD27 1.5592 154 4-OCH3 -CH (CH3) 2 -CH3 -OC4H9 (i) S nD27 1.5482 155 4-OCH3 -CH (CH3) 2 -CH3 -OC4H9 (i) O nD24 1.5262 156 4-CH3 -CH (CH3) 2 -CH3 -OC2H5 S nD27 1.5453 157 4-CH3 -CH (CH3) 2 -CH3 -OC4H9 (i) S nD26 1.5566 158 2-CH (CH3) 2 -CH (CH3) 2 -CH3 -OCH3 S nD25 1.5566 159 2-CH (CH3) 2 -CH (CH3) 2 -CH3 -OC2H5 S m.p. 64-66 ° C 160 2-CH (CH3) 2 -CH (CH3) 2 -CH3 -OC4H9 (i) O nD23 1.5223 161 2-CH (CH3) 2 -CH (CH3) 2 -CH3 -OC4H9 (i) S nD23 1.5420 162 4-CH (CH3) 2 -CH (CH3) 2 -CH3 -OC2H5 S nD25 1.5542 163 4-C (CH3) 3 -CH (CH3s) 2 -CH3 -OC2H5 s m.p. 54-590C 164 4-CH (CH3) 2 -CH (CH3) 2 -CH3 -OC4H9 (i) S M.p. 64-73 ° C 165 H -CH (CH3) 2 -CH3 -OC2H5 O m.p. 67-68 ° C Table (continued) Ex. R (n) R1 R2 R3 X nD or Fp 166 4-F -CH (CH3) 2 -N (CH3) 2 -OC2H5 O nD23 1.5192 167 2-Cl -CH3 -NHCH3 -OC2H5 O nD24 1.5534 168 2-Cl -CH3 -NHCH (CH3) 2 -OC2H5 O nD24 1.5473 169 2-Cl -CH3 -NHCH2 CH = CH2 -OC2H5 O nD24 1.5513 170 2-Cl -CH3 -NH-C4H9 (n) -OC2H5 O nD24 1.5583 171 3-Cl -CH3 -NHCH3 -OC2H5 O nD24 1.5548 172 3-Cl -CH3 -NHCH (CH3) 2 -OC2H5 O nD24 1.5388 173 3-Cl -CH3 -NHCH2 CH = CH2 -OC2H5 O nD24 1.5546 174 3-Cl -CH3 -NH-C4H9 (n) -OC2H5 O nD24 1.5410 175 4-Cl -CH3 -NHCH3 -OC2H5 O - 176 4-Cl -CH3 -NHCH (CH3) 2 -OC2H5 O nD24 1.5413 177 4-Cl -C2H5 -N (CH3) 2 -OC2H5 O nD28 1.5403 178 4-Cl -C4H9 (sec) -N (CH3) 2 -OC2H5 O nD24 1.5329 179 4-Cl -C4H9 (sec) -NHCH (CH3) 2 -OC2H5 O nD24 1.5316 180 4-Br -CH (CH3) 2 -N (CH3) 2 -OC2H5 O nD24 1.5465 181 4-Br -CH (CH3) 2 -NHCH (CH3) 2 -OC2H5 O nD24 1.5412 182 2,3-Cl -CH3 -NHCH3 -OC2H5 O nD24 1.5585 183 2,3-Cl -CH3 -NHCH (CH3) 2 -OC2H5 O nD24 1.5452 184 2,4-Cl -CH3 -NHCH3 -OC2H5 O nD24 1.5604 185 2,4-Cl -CH3 -NHCH (CH3) 2 -OC2H5 O nD24 1.5405 186 2,4-Cl -CH3 -NHCH2 CH = CH2 -OC2H5 O nD24 1.5542 187 2,4-Cl -CH3 -NH-C4H9 (n) -OC2H5 O nD24 1.5447 188 2,5-Cl -CH3 -NHCH3 -OC2H5 O nD24 1.5645 189 2,5-Cl -CH3 -NHCH (CH3) 2 -OC2H5 O nD24 1.5502 Table (continued) Ex. R (n) R1 R2 R3 X nD or Fp 190 2,5-Cl -CH3 -NHCH2CH = CH2 -OC2H5 O nD24 1.5597 191 2,5-Cl -CH3 -NH-C4H9 (n) -OC2H5 O nD24 1.5474 192 3,4-C1-CH3 -NH-CH3 -OC2H5 O nD24 1.5620 193 3,4-Cl -CH3 -NHCH (CH3) 2 -OC2H5 O nD24 1.5451 194 3,4-Cl -CH3 -NH-C4H9 (n) -OC2H5 O nD24 1.5495 195 4-C (OH) 2 -CH (CH3) 2 -NH-CH3 -OC2H5 O nD24 1.5226 196 4-C (OH) 2 -CH (CH3) 2 -NHCH (CH3) 2 -OC2H5 O nD24 1.5170 197 3-Cl -CH (CH3) 2 -NH-CH3 -OC2H5 O nD24 1.4980 198 3-Cl -CH (CH3) 2 -N (CH3) 2 -OC2H5 O nD24 1.4835 199 3-Cl -CH (CH3) 2 -NHCH (CH3) 2 -OC2H5 O nD24 1.4953 200 3-Cl -C4H9 (sec) -NH-CH3 -OC2H5 O nD24 1.4994 201 3-Cl -C4H9 (sec) -N (CH3) 2 -OC2H5 O nD24 1.4930 202 3-Cl -C4H9 (sec) -NHCH (CH3) 2 -OC2H5 O nD28 1.4953 203 3-Cl -C4H9 (sec) -NHCH2 CH = CH2 -OC2H5 O nD24 1.5047 204 H -CH (CH3) 2 -NH-C3H7 (n) -C2H5 S M.p. 76-78 ° C 205 4-Cl -CH (CH3) 2 -N (CH3) 2 -OCH5 O - Ex. R (n) R1 R2 R3 X nD or Fp 206 4-F -CH (CH3) 2 -C2H5 -OC2H5 S nD24 1.5254 207 4-F -CH (CH3) 2 -C3H7 (n) -OC5H7 (n) S nD24 1.5208 FO.Z5MULIERUNGSBEISPIELE Example A: A wettable powder easily dispersible in water is obtained by containing 25 parts by weight of dithiophosphoric acid S [N- (4-chlorophenyl) -N-isopropyl-carbamoylmethyl] -O, O-diethyl ester as active ingredient, 64 parts by weight of kaolin Mixing quartz as an inert substance, 10 parts by weight of lignosulphonic acid potassium and 1 part by weight of oleylmethyltauric acid sodium as wetting and dispersing agent and grinding in a pin mill.

Beispiel B: Ein Stäubemittel, das sich zur Anwendung als Unkrautvertilgungsmittel gut eignet, wird erhalten, indem man 10 Gewichtsteile Dithiophosphorsäure-S [N-(4-chlorphenyl)-N-isopropyl-carbamoylmethyl]-O,O-diäthylester als Wirkstoff und 90 Gewichtsteile Talkum als Inertstoff mischt und in einer Schlagmühle zerkleinert.Example B: A dust that can be used as a herbicide well suited, is obtained by adding 10 parts by weight of dithiophosphoric acid S [N- (4-chlorophenyl) -N-isopropyl-carbamoylmethyl] -O, O-diethyl ester mixes as active ingredient and 90 parts by weight of talc as inert and in a hammer mill crushed.

Beispiel C: Ein emulgierbares Konzentrat besteht aus 15 Gewichtsteilen Dithiophosphorsäure-S [N-(4-chlorphenyl)-N-isopropyl-carbamoylmethyl]-O,O-diäthylester, 75 Gewichtsteilen Cyclohexanon als Lösungsmittel und 10 C-ewichtsteilen oxäthyliertes Nonylphenyl (10 AeO) als Emulgator.Example C: An emulsifiable concentrate consists of 15 parts by weight Dithiophosphoric acid S [N- (4-chlorophenyl) -N-isopropyl-carbamoylmethyl] -O, O-diethyl ester, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxethylated Nonylphenyl (10 AeO) as an emulsifier.

Beispiel D: Ein Granulat besteht z.B. aus etwa 2-15 Gewichtsteilen Dithiophosphorsäure-S [N-(4-chlorphenyl)-N-N-isopropyl-carbamoylmethyl]-O,O-diäthylester und inertem Granulatträgermaterial, z.B.Attalpulgit, Bimsgranulat und/oder Quarz sand.Example D: A granulate consists e.g. of about 2-15 parts by weight Dithiophosphoric acid S [N- (4-chlorophenyl) -N-N-isopropyl-carbamoylmethyl] -O, O-diethyl ester and inert granulate carrier material, e.g. total pulgite, pumice granulate and / or quartz sand.

ANWENDUNGSBEISPIELE Beispiel I: Weizenpflanzen wurden im 3-Blattstadium mit Konidien des Weizenmehltaus (Erysiphe gràminis) stark infiziert und in einem Gewächshaus bei 200C und einer relativen Luftfeuchte von 90-95 % aufgestellt. 5 Tage nach Inokulation wurden die Pflanzen mit den in Tabelle I genannten Verbindungen in den llirkstofSkonzenGrationen von 500, 250, 120 und 60 mg/Liter wäßriger Spritzbrühe tropfnaß gespritzt. Der Versuch wurde vierfach angelegt.APPLICATION EXAMPLES Example I: Wheat plants were at the 3-leaf stage heavily infected with conidia of wheat powdery mildew (Erysiphe gràminis) and in one Greenhouse set up at 200C and a relative humidity of 90-95%. 5 Days after inoculation, the plants were treated with the compounds listed in Table I. in the active ingredient concentrations of 500, 250, 120 and 60 mg / liter of aqueous spray liquor sprayed dripping wet. The experiment was carried out four times.

Nach einer Inkubationszeit von 10 Tagen wurden die Pflanzen auf Befall mit Weizenmehltau untersucht. Der Befallsgrad wurde ausgedrückt in % befallener Blattfläche bezogen auf unbehandelte, infizierte Kontrollpflanzen (= 100 %). Tabelle I: Verbindung mit Weiyemmehltau befallene Blattfläche gemäß in % bei mg Wirkstoff/Liter Spritzbrühe Beispiel 500 250 120 60 138 0 0 5 15 122 0 3 5 25 158 0 0 5 15 159 0 3 5 15 63 0 3 5 - 72 0 5 15 - 66 0 5 15 - 91 0 3 15 - 92 0 5 15 - 204 0 0 5 15 205 0 3 5 15 Vgl.-Mittel A 3 10 25 40 unberhandelte, 100 infizierte Pflanzen Vergleichsmittel A = O-Äthyl-S,S-diphenyl-dithio-phosphat - = nicht bestimmt Beispiel II: Gurkenpflanzen wurden im 2-Blattstadium mit einer Konidiensuspension von Gurkemehltau (Erysiphe cichoracearum) stark inokuliert. Nach einer Autrocknungszeit der Sporensuspension von 30 Minuten wurden die Pflanzen in einem Gewächshaus bei 220C und 90 % relativer Luftfeuchte aufgestellt. 3 Tage nach Infektion wurden die Pflanzen mit den in Tabelle 11 genannten Verbindungen und Wirkstoffkonzentrationen gespritzt. Der Versuch wurde vierfach angegelt. .acr 10- 14 Tagen erfolgte die Bonitur. Der Befallsgrad wurde ausgedrückt in da befallener Blattfläche bezogen auf unbehandelte, infizierte Kontrollpflanzen (=100 %).After an incubation period of 10 days, the plants were examined for infestation with wheat powdery mildew. The degree of infection was expressed in% of infected leaf area based on untreated, infected control plants (= 100%). Table I: Connection with powdery mildew infested leaf area according to in% at mg active ingredient / liter spray liquid Example 500 250 120 60 138 0 0 5 15 122 0 3 5 25 158 0 0 5 15 159 0 3 5 15 63 0 3 5 - 72 0 5 15 - 66 0 5 15 - 91 0 3 15 - 92 0 5 15 - 204 0 0 5 15 205 0 3 5 15 Compare mean A 3 10 25 40 untreated, 100 infected plants Comparative agent A = O-ethyl-S, S-diphenyl-dithio-phosphate - = not determined Example II: Cucumber plants were heavily inoculated in the 2-leaf stage with a conidia suspension of cucumber powdery mildew (Erysiphe cichoracearum). After the spore suspension had dried for 30 minutes, the plants were placed in a greenhouse at 220 ° C. and 90% relative humidity. 3 days after infection, the plants were sprayed with the compounds and active ingredient concentrations mentioned in Table 11. The attempt was fished four times. The rating took place within 10-14 days. The degree of infection was expressed in the infected leaf area based on untreated, infected control plants (= 100%).

Tabelle II: Verbindung mit Gurkenmehltau befallene Blattfläche gemäß in % bei mg. Wirkstoff/Liter Spritzbrühe Beispiel 500 250 120 60 122 0 0 5 15 158 0 0 5 25 159 0 0 3 5 141 0 0 5 25 153 0 0 5 25 156 0 3 5 15 66 0 3 5 15 67 0 3 5 25 91 0 3 15 25 Vgl.-Mittel A 3 10 25 100 unbehandelte, 100 infizierte Pflanzen Beispiel Weizenprlanzen wurden mit den in Tabelle III genannten Verbindungen in den Äufwandmengen von 500, 250, 120 und 60 mg/ Liter Spritzbrühe tropfnaß behandelt.Table II: Connection with cucumber powdery mildew infested leaf area according to in% at mg. Active ingredient / liter of spray liquid Example 500 250 120 60 122 0 0 5 15 158 0 0 5 25 159 0 0 3 5 141 0 0 5 25 153 0 0 5 25 156 0 3 5 15 66 0 3 5 15 67 0 3 5 25 91 0 3 15 25 Compare mean A 3 10 25 100 untreated, 100 infected plants EXAMPLE Wheat plants were treated to runoff with the compounds listed in Table III in amounts of 500, 250, 120 and 60 mg / liter of spray liquor.

Nach dem Abtrocknen des Wirkstoffbelages wurden die Pflanzen mit Sporen des Weizenbraunrostes (Puccinia triticira) stark inokuliert und fir 24 Stunden in eire Klimakammer mit 100 % realtiver Luftfeuchte und 20°C gestellt. Anschließend kamen die Pflanzen in ein Gewächshaus und wurden hier 14 Tage nach Inokulation auf Befall mit Weizenbraunrost untersucht.After the active substance coating had dried off, the plants became spore of wheat rust (Puccinia triticira) heavily inoculated and for 24 hours in A climatic chamber with 100% relative humidity and 20 ° C is placed. Afterward the plants came into a greenhouse and were here 14 days after inoculation Investigation of brown rust infestation.

Tabelle III: Verbindung mit Weizenbraunrost befallene Blattfläche gemäß in % bei mg. Wirkstoff/Liter Spritzbrühe Beispiel 500 250 120 60 108 0 0 5 15 109 0 0 15 25 160 0 : 3 5 15 121 0 3 5 10 122 0 5 15 35 158 0 0 5 15 6 o 5 15 - 5 o 5 25 - 16 0 3 15 - 44 o 5 25 - 45 0 5 35 - 22 0 3 15 - 24 0 5 25 - 199 0 5 15 - 198 0 5 15 - 178 o 3 5 - Vgl.-Mittel A 3 10 35 - unbehandelte infizierte 100 Pflanzen Beispiel IV: Reispflanzen wurden im 4-Blattstadium mit den in Tabelle IV angegebenen Verbindungen in Konzentrationen von 500, 250, 120 und 60 mg Wirkstoff pro Liter Spritzbrühe tropfnaß gespritzt.Table III: Leaf area infested with wheat brown rust according to in% at mg. Active ingredient / liter of spray liquid Example 500 250 120 60 108 0 0 5 15 109 0 0 15 25 160 0: 3 5 15 121 0 3 5 10 122 0 5 15 35 158 0 0 5 15 6 o 5 15 - 5 o 5 25 - 16 0 3 15 - 44 o 5 25 - 45 0 5 35 - 22 0 3 15 - 24 0 5 25 - 199 0 5 15 - 198 0 5 15 - 178 o 3 5 - Compare mean A 3 10 35 - 100 untreated infected plants Example IV: Rice plants in the 4-leaf stage were sprayed to runoff with the compounds listed in Table IV in concentrations of 500, 250, 120 and 60 mg of active ingredient per liter of spray liquor.

Nach dem Abtrocknen des Spritzbelages wurden die Pflanzen mit einer Sporensuspension von Piricularia oryzae gleichmäßig besprüht und für 48 Stunden in eine dunkel gehaltene Klimakammer mit 250C und 100 % relativer Luftfeuchte gestellt. Anschließend wurden die Pflanzen in einem Gewächshaus bei 250C und 85 % relativer Luftfeuchte gehalten und 14 Tage nach Inokulation auf Befall mit Piricularia oryzae untersucht. Der Beffalsgrad wurde ausgedrückt in % beffallener Blattfläche bezogen auf unbehandelte, infizierte Kontrollpflanzen (= 100 %).After the spray coating had dried off, the plants were treated with a Spore suspension of Piricularia oryzae sprayed evenly and for 48 hours placed in a dark climate chamber with 250C and 100% relative humidity. The plants were then placed in a greenhouse at 250 ° C. and 85% relative Maintained humidity and 14 days after inoculation for infestation with Piricularia oryzae examined. The degree of Beffals was expressed as a percentage of the infected leaf area on untreated, infected control plants (= 100%).

Tabelle IV Verbindung mit Piricularia oryzae befallene Blattfläche gemäß in % bei mg Wirkstoff/Liter Spritzbrühe Beispiel 1000 500 250 120 il 0 3 15 25 49 O 3 5 15 52 0 0 3 15 27 0 5 15 35 125 0 3 15 206 0 5 15 Vgl.-Mittel A total total sehr stark stark verbrannt verbrannt verbrannt verbrannt 25 unbehandelte infizierte 100 Pflanzen Aus den Tabellen I - IV geht die gegenüber dem Vergleichsmittel A erheblich überlegene fungizide Wirkung der beanspruchten Verbindungen hervor. Auch hinsichtlich der Phytotoxizität zeigen die beanspruchten Verbindungen gegenüber dem Vergleichsmittel deutliche Vorteile.Table IV Affected leaf surface in association with Piricularia oryzae according to in% at mg active ingredient / liter spray liquid Example 1000 500 250 120 il 0 3 15 25 49 O 3 5 15 52 0 0 3 15 27 0 5 15 35 125 0 3 15 206 0 5 15 Compare mean A total total very strong strong burned burned burned burned 25th untreated infected 100 plants Tables I-IV show the fungicidal action of the claimed compounds, which is considerably superior to that of comparative agent A. The claimed compounds also show clear advantages over the comparative agent with regard to phytotoxicity.

Claims (2)

Patentansprüche 0 Fungizide Mittel gekennzeichnet durch einen wirksamen Gehalt an einer Verbindung der allgemeinen Formel I worin R = gleiche oder verschiedene Reste aus der Gruppe H, Halogen, (C1-C4)-Alkyl, (C1-C2)-Halogenalkyl, (C1-C2)-Alkoxy, NO2, CN, SO2CH3, COOCH3, S02NH2, R1 = (C1-C6)-Alkyl, R2 = (C1-C6)-Alkyl, (C1-C6)-Alkoxy, (C1-C6)-Alkylamino, (C3-C6)--Alkenylamino, Di-(C1-C6)-alkylamino R3 = (C1-C2)-Alkyl, (C1-C6)-Alkoxy, mit der Maßgabe, daß R2 und R3 nicht gleichzeitig Alkyl sind, R4 = H oder Methyl, X = Sauerstoff oder Schwefel, und n = eine ganze Zahl von 1 - 3 ist.Claims 0 Fungicidal agents characterized by an effective content of a compound of the general formula I. where R = identical or different radicals from the group H, halogen, (C1-C4) -alkyl, (C1-C2) -haloalkyl, (C1-C2) -alkoxy, NO2, CN, SO2CH3, COOCH3, SO2NH2, R1 = (C1-C6) -alkyl, R2 = (C1-C6) -alkyl, (C1-C6) -alkoxy, (C1-C6) -alkylamino, (C3-C6) -alkenylamino, di- (C1-C6) -alkylamino R3 = (C1-C2) -alkyl, (C1-C6) -alkoxy, with the proviso that R2 and R3 are not simultaneously alkyl, R4 = H or methyl, X = oxygen or sulfur, and n = a whole Number from 1 to 3 is. 2) Verwendung von Verbindungen der Formel I zur Bekämpfung von Pilzkrankheiten oder Pilzbefall bei Pflanzen und toten organischen Substraten. 2) Use of compounds of the formula I for combating fungal diseases or fungal attack on plants and dead organic substrates.
DE19762604225 1976-02-04 1976-02-04 Fungicides for plant and inanimate organic materials - contg. S-phenyl-carbamoyl-methyl dithio-phosphate and thio-phosphonate derivs. Pending DE2604225A1 (en)

Priority Applications (39)

Application Number Priority Date Filing Date Title
DE19762604225 DE2604225A1 (en) 1976-02-04 1976-02-04 Fungicides for plant and inanimate organic materials - contg. S-phenyl-carbamoyl-methyl dithio-phosphate and thio-phosphonate derivs.
NL7700930A NL7700930A (en) 1976-02-04 1977-01-28 PLANT PROTECTION PRODUCT.
BG035295A BG27723A3 (en) 1976-02-04 1977-01-31 Herbicide means
BG7942073A BG28979A4 (en) 1976-02-04 1977-01-31 Insecticide means
BG7742074A BG28980A4 (en) 1976-02-04 1977-01-31 Nematocide means
EG58/77A EG12788A (en) 1976-02-04 1977-02-01 Pesticidal agents
TR19568A TR19568A (en) 1976-02-04 1977-02-01 HARMFUL HERBS AND MUSHROOMS OELDUERUECUE (HERBISID AND FUNGISID) SUBSTANCES
US05/764,995 US4140774A (en) 1976-02-04 1977-02-02 Method of combating nematodes using S-(amidocarbonyl)-methyl-O-alkyl-mono(di)thiophosphoric acid ester amides
RO7789255A RO70320A (en) 1976-02-04 1977-02-02 PROCESS FOR OBTAINING COMPOUNDS OF THIOPHOSPHORIC ACID
NZ183238A NZ183238A (en) 1976-02-04 1977-02-02 Organophosphorus amides and herbicidal,insecticidal,acaricidal and nematocidal compositions
AT64177A AT355860B (en) 1976-02-04 1977-02-02 PEST CONTROL
LU76690A LU76690A1 (en) 1976-02-04 1977-02-02
CH125277A CH631721A5 (en) 1976-02-04 1977-02-02 Pesticides.
FI770368A FI770368A (en) 1976-02-04 1977-02-02
PH19410A PH12483A (en) 1976-02-04 1977-02-02 Pesticidal thionophosphonic acid amides
IL51372A IL51372A (en) 1976-02-04 1977-02-02 (di)-thiophosphoric acid n-arylcarbamoyl ester process fortheir preparation and insecticidal acaricidal nematocidal and herbicidal compositons comprising them
BR7700642A BR7700642A (en) 1976-02-04 1977-02-02 FUNGIZIDE MITTEL
IT19896/77A IT1078001B (en) 1976-02-04 1977-02-02 PRODUCTS FOR THE PROTECTION OF PLANTS
DD7700197194A DD129105A5 (en) 1976-02-04 1977-02-02 PROCESS FOR THE PREPARATION OF NEW THIOPHOSPHATES
GB4194/77A GB1565894A (en) 1976-02-04 1977-02-02 Pesticidal organic phosphorus compounds processes for their preparation and compositions containing them
CA271,007A CA1088065A (en) 1976-02-04 1977-02-03 Pesticidal agents
JP52010342A JPS6013039B2 (en) 1976-02-04 1977-02-03 plant protection agent
IE226/77A IE44595B1 (en) 1976-02-04 1977-02-03 Pesticidal organic phosphorus compounds, processes for theior preparation and compositions containing them
YU00284/77A YU28477A (en) 1976-02-04 1977-02-03 Process for preparing thiophosphoric acid derivatives
DK45977A DK149346C (en) 1976-02-04 1977-02-03 COMPOUNDS FOR USE IN HERBICIDES, INSECTICIDES, ACARICIDES AND NEMATODICIDES FOR PLANT PROTECTION AND OTHER TECHNICAL PURPOSES AND USE OF THE COMPOUNDS
FR7702989A FR2340324A1 (en) 1976-02-04 1977-02-03 ORGANOPHOSPHORUS COMPOUNDS AND PESTICIDAL PRODUCTS WHICH CONTAIN IT
PT66151A PT66151B (en) 1976-02-04 1977-02-03 PROCESS FOR THE PREPARATION OF PHOSPHOROUS ORGANIC COMPOUNDS AND ACARICIDAL AND NEMATICIDE INSECTICIDAL HERBICIDE COMPOSITIONS CONTAINING THE SAME
ZA770604A ZA77604B (en) 1976-02-04 1977-02-03 Pesticidal agents
GR52705A GR70331B (en) 1976-02-04 1977-02-03
AU21907/77A AU506483B2 (en) 1976-02-04 1977-02-03 Thiophosphate derivatives
OA56060A OA05558A (en) 1976-02-04 1977-02-04 Organophosphorus compounds and pesticide products which contain them.
BE174697A BE851126A (en) 1976-02-04 1977-02-04 ORGANOPHOSPHORUS COMPOUNDS AND PESTICIDAL PRODUCTS WHICH CONTAIN IT
CS77752A CS199286B2 (en) 1976-02-04 1977-02-04 Fungicides,insecticides,acaricides,nematocides and herbicides and method of producing active compounds
SE7701260A SE427663B (en) 1976-02-04 1977-02-04 PHOSPHORIC ACID EERAMIDS FOR USE AS A PROTECTIVE AGENT
MX775415U MX4478E (en) 1976-02-04 1977-02-04 IMPROVED PROCEDURE FOR OBTAINING ACETANILIDOTIOFOSFATO DERIVATIVES
AR266430A AR219488A1 (en) 1976-02-04 1977-02-08 NEW DERIVATIVES OF N-PHENYL-N-ALKYL CARBAMOYL METHYLLITHIUM OR DITIOPHOSPHATES, USEFUL FOR PURPOSES PHYTOSANITE RIVERS, COMPOSITIONS CONTAINING THEM AND PROCEDURE FOR PREPARING THEM
KE3127A KE3127A (en) 1976-02-04 1981-05-06 Pesticidal organic phosphorus compounds,process for their preparation and compositions containing theim
YU01899/82A YU189982A (en) 1976-02-04 1982-08-24 Process for obtaining derivatives of thiophsphoric acid
MY6/82A MY8200006A (en) 1976-02-04 1982-12-30 Pesticidal organic phosphorus compounds processes for their preparation and compositions containing them

Applications Claiming Priority (1)

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DE19762604225 DE2604225A1 (en) 1976-02-04 1976-02-04 Fungicides for plant and inanimate organic materials - contg. S-phenyl-carbamoyl-methyl dithio-phosphate and thio-phosphonate derivs.

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102260287A (en) * 2010-05-31 2011-11-30 中国中化股份有限公司 Preparation method of herbicide anilofos
CN113698430A (en) * 2021-10-29 2021-11-26 潍坊新绿化工有限公司 Preparation method of herbicide anilofos

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102260287A (en) * 2010-05-31 2011-11-30 中国中化股份有限公司 Preparation method of herbicide anilofos
CN102260287B (en) * 2010-05-31 2014-07-09 中国中化股份有限公司 Preparation method of herbicide anilofos
CN113698430A (en) * 2021-10-29 2021-11-26 潍坊新绿化工有限公司 Preparation method of herbicide anilofos

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