DE2633159A1 - S-Phenylcarbamoylmethyl (di)thio-phosphoramidates - for uses as herbicides, insecticides, acaricides and nematocides - Google Patents

S-Phenylcarbamoylmethyl (di)thio-phosphoramidates - for uses as herbicides, insecticides, acaricides and nematocides

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Publication number
DE2633159A1
DE2633159A1 DE19762633159 DE2633159A DE2633159A1 DE 2633159 A1 DE2633159 A1 DE 2633159A1 DE 19762633159 DE19762633159 DE 19762633159 DE 2633159 A DE2633159 A DE 2633159A DE 2633159 A1 DE2633159 A1 DE 2633159A1
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Prior art keywords
formula
compounds
alkyl
herbicides
active ingredient
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DE19762633159
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German (de)
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DE2633159C2 (en
Inventor
Hermann Bieringer
Gerhard Dipl Chem Dr Hoerlein
Peter Langelueddeke
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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Priority to DE19762633159 priority Critical patent/DE2633159C2/en
Priority to NL7700930A priority patent/NL7700930A/en
Priority to BG7742074A priority patent/BG28980A4/en
Priority to BG7735295A priority patent/BG27723A3/en
Priority to BG7942073A priority patent/BG28979A4/en
Priority to TR19568A priority patent/TR19568A/en
Priority to EG58/77A priority patent/EG12788A/en
Priority to CH125277A priority patent/CH631721A5/en
Priority to PH19410A priority patent/PH12483A/en
Priority to IL51372A priority patent/IL51372A/en
Priority to DD7700197194A priority patent/DD129105A5/en
Priority to AT64177A priority patent/AT355860B/en
Priority to FI770368A priority patent/FI770368A/fi
Priority to NZ183238A priority patent/NZ183238A/en
Priority to BR7700642A priority patent/BR7700642A/en
Priority to IT19896/77A priority patent/IT1078001B/en
Priority to GB4194/77A priority patent/GB1565894A/en
Priority to RO7789255A priority patent/RO70320A/en
Priority to LU76690A priority patent/LU76690A1/xx
Priority to US05/764,995 priority patent/US4140774A/en
Priority to GR52705A priority patent/GR70331B/el
Priority to YU00284/77A priority patent/YU28477A/en
Priority to IE226/77A priority patent/IE44595B1/en
Priority to PT66151A priority patent/PT66151B/en
Priority to AU21907/77A priority patent/AU506483B2/en
Priority to FR7702989A priority patent/FR2340324A1/en
Priority to HUHO001956 priority patent/HU184138B/en
Priority to DK45977A priority patent/DK149346C/en
Priority to JP52010342A priority patent/JPS6013039B2/en
Priority to CA271,007A priority patent/CA1088065A/en
Priority to CS77752A priority patent/CS199286B2/en
Priority to MX775415U priority patent/MX4478E/en
Priority to OA56060A priority patent/OA05558A/en
Priority to SE7701260A priority patent/SE427663B/en
Priority to AR266430A priority patent/AR219488A1/en
Publication of DE2633159A1 publication Critical patent/DE2633159A1/en
Priority to KE3127A priority patent/KE3127A/en
Application granted granted Critical
Publication of DE2633159C2 publication Critical patent/DE2633159C2/en
Priority to YU01899/82A priority patent/YU189982A/en
Priority to MY6/82A priority patent/MY8200006A/en
Expired 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)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

New S-(phenylcarbamoylmethyl) (di)thiophosphoramidates are of formula (I): In the formula each R is halogen, 1-6C alkyl, 1-3C haloalkyl, MeO, EtO, NO2 or MeS; R1 is H or 1-6C alkyl; R2 is 1-6C alkylamino, 3-8C alkenylamino, di(1-6C alkyl)amino, 5-8C cycloalkylamino, or a satd. N heterocycle contg. 4-8C atoms, 1 or 2 of which can be in a side chain, one of the ring CH2 gps. being opt. replaced by O or S; R3 is 1-6C alkyl; X is O or S; n = 0-3. Cpds. (I) are useful as selective herbicides, insecticides, acaricides and nematocides. As herbicides, they can be used to control, e.g., Alopecurus and Galium in cereals, Echinochloa in maize, and Setaria in soya or cotton. In an example, (I; n = O, R1 = i-Pr, R2 = NHMe, R3-Et, X = O) was prepd. from NH4S(O)P(OEt)NHMe and N-isopropyl-chloroacetanilide.

Description

Herbizide MittelHerbicidal agents

Gegenstand der vorliegenden Anmeldung sind Verbindungen der allgemeinen Formel worin R = gleiche oder verschiedene Substituenten aus der Gruppe Halogen, (C1 -C6) -Alkyl, (C1 03) -Halogenalkyl, (C1-C2)-Alkoxy, NO2, CN, SO2, CH3, SO2-NH2 oder SCH3, R1 = Wasserstoff oder (Cl-C6)-Alkyl, R3 = (C1-C6)-Alkyl, R2 = (C1-C6)-Alkylamino, (C3-C8)-Alkylenylamino, N,N-Di-(C1-C6)-alkylamino, (C5-C8) Cycloalkylamino oder einen gesättigten N-Heterocyclus mit insgesamt 4-8 C-Atomen, von denen 1-2 sich in der Seitenkette befinden können und wobei eine Ring-CH2-Gruppe auch durch Sauerstoff cder Schwefel ersetzt sein kann, X = Sauerstoff oder Schwefel, sowie n = 0 oder eine ganze Zahl von 1-3 bedeuten.The present application relates to compounds of the general formula where R = identical or different substituents from the group consisting of halogen, (C1-C6) -alkyl, (C1 03) -haloalkyl, (C1-C2) -alkoxy, NO2, CN, SO2, CH3, SO2-NH2 or SCH3, R1 = Hydrogen or (Cl-C6) -alkyl, R3 = (C1-C6) -alkyl, R2 = (C1-C6) -alkylamino, (C3-C8) -alkylenylamino, N, N-di- (C1-C6) -alkylamino, (C5-C8) cycloalkylamino or a saturated N-heterocycle with a total of 4-8 carbon atoms, of which 1-2 can be in the side chain and where one ring CH2 group can also be replaced by oxygen or sulfur can mean X = oxygen or sulfur, and n = 0 or an integer from 1-3.

Bevorzugte Reste in der allgemeinen Formel (I) sind für R = F, Cl, (C1-C4)-Alkyl, CF3, NO2, CN, R1 = H, (C1-C4)-Alkyl, R3 = (C1-C4)-Alkyl, R2 = (C1-C4)-Alkylamino, (C3-C6)-Alkenylamino, N,N-Di-(C1-C4)-lkylamino, (C5-C8)-Cycloalkylamino, Morpholino, Piperidino, (C1 -C2) -Alkylpiperidino und Pyrrolidino, Die Verbindungen der Formel (1) erhält man in an sich bekannter Weise, indem man a) Verbindungen der Formel mit Phosphorverbindungen der Formel worin jeweils einer der Reste A und B 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, oder b) zunächst Verbindungen der Formel IV mit Verbindungen der Formel III umsetzt und die erhaltenen Zwischenprodukte der Formel V durch Umsetzung mit Anilinen der Formel VI in die Verbindunaen der Formel 1 überführt worin R4 bevorzugt niederes Alkvl oder Phenvl bedeutet.Preferred radicals in the general formula (I) are for R = F, Cl, (C1-C4) -alkyl, CF3, NO2, CN, R1 = H, (C1-C4) -alkyl, R3 = (C1-C4) -Alkyl, R2 = (C1-C4) -alkylamino, (C3-C6) -alkenylamino, N, N-di- (C1-C4) -lkylamino, (C5-C8) -cycloalkylamino, morpholino, piperidino, (C1 - C2) -Alkylpiperidino and Pyrrolidino, The compounds of the formula (1) are obtained in a manner known per se by a) compounds of the formula with phosphorus compounds of the formula in which in each case one of the radicals A and B 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, or b) initially compounds of the formula IV Reacts with compounds of the formula III and the intermediate products of the formula V obtained by reaction with anilines of the formula VI converted into the compounds of formula 1 in which R4 is preferably lower alkyl or phenyl.

a) Die Phosphorverbinduna'en der Formel (III) ( B = SY) reagieren mit den Chloracetaniliden der Formel (II) ( A = Hal) ohne Schwierigkeiten, wobei vorteilhaft Temperaturen zwischen 0° und +1200C, vorzugsweise +100 bis +80°C, anqewendet werden.a) The phosphorus compounds of formula (III) (B = SY) react with the chloroacetanilides of the formula (II) (A = Hal) without difficulty, with temperatures between 0 ° and + 1200C, preferably +100 to + 80 ° C, are advantageously used will.

Es ist ratsam, diese Umsetzung in Gegenwart eines gegenüber den Reaktionsteilnehmern inerten Lösungs- oder Verdünnungsmittels durchzuführen. In Betracht kommen in erster Linie niedere aliphatische Ketone wie Aceton oder Methyläthylketon, Alkanole wie Methanol, Äthanol oder Isopropanol, Ester wie Essigsäureäthylester, Nitrile, N-alkylierte Säureamide wie Dimethylformamid, Äther wie Dioxan, Glykoldimethäther oder Tetrahydrofuran, chlorierte Kohlenwasserstoffe wie Chloroform oder Tetrachlorkohlenstoff und Wasser sowie Gemische solcher Lösungsmittel. It is advisable to carry out this reaction in the presence of one facing the reactants carry out inert solvent or diluent. They come into consideration first Line lower aliphatic ketones such as acetone or methyl ethyl ketone, alkanols such as Methanol, ethanol or isopropanol, esters such as ethyl acetate, nitriles, N-alkylated Acid amides such as dimethylformamide, ethers such as dioxane, glycol dimethether or tetrahydrofuran, chlorinated hydrocarbons such as chloroform or carbon tetrachloride and water as well as mixtures of such solvents.

Die Reaktion erfolgt unter Austausch des Halogenatoms der Chloracetanilide, Daher führt man die Umsetzung entweder unter Zusatz säurebindender Mittel odr mit eii Salzen, insbesondere mit Alkalimetall- und Ammoniumsalzen der Phosphorverbindungen durch. Als säurebindende Mittel sind die Alkalimetalhydroxide und -carbonate bevorzugt; es können aber auch tertiäre Stickstoffbasen wie Pyridin ocr Triäthylamin verwendet werden. The reaction takes place with exchange of the halogen atom of the chloroacetanilide, The reaction is therefore carried out either with the addition of acid-binding agents or with eii salts, especially with alkali metal and ammonium salts of the phosphorus compounds by. The alkali metal hydroxides and carbonates are preferred as acid-binding agents; however, tertiary nitrogen bases such as pyridine or triethylamine can also be used will.

Die £alogeiiessigsäureanilide der Formel (II) und ihre Herstellung sind in der Literatur beschrieben. The alogeii acetic anilides of the formula (II) and their preparation are described in the literature.

Die-SY-Verbindungen gemäß der Formel (III) sind bekannt und nach üblichen Methoden leicht zugänglich. The-SY compounds according to the formula (III) are known and according to easily accessible to usual methods.

Umgekehrt kann man auch Thioglykolsäureanilide der Formel (II) ( A = SY) mit Halogen-phosphorverbindungen der Formel (III) ! B = Hal) umsetzen, wobei im Falle A = SH ebenfalls in Gegenwart eines säurebindenden Mittels gearbeitet wird. Conversely, you can also use thioglycolic anilides of the formula (II) ( A = SY) with halophosphorus compounds of the formula (III)! B = Hal), where in the case of A = SH, it is also carried out in the presence of an acid-binding agent.

Im allgemeinen werden etwa stöchiometrische Mengen der Reaktionspartner angewendet, jedoch kann ein Überschuß der Verbindung der Formel III von 5 - 10 % vorteilhaFt sein. In general, about stoichiometric amounts of the reactants will be used applied, but an excess of the compound of formula III of 5 - 10% be advantageous.

Die Reaktion wird vorzugsweise in Gegenwart eines unter Reaktionsbedingungen inerten Lösungsmittels durchgeführt. Als solche sind z.B. die oben genannten verwendbar. Die Reak.tionstemperaturen können innerhalb eines größeren Bereiches variiert werden, vorzugsweise arbeitet man zwischen +50 und +1200C. Als säurebindende Mittel sind ebenfalls die oben genannten verwendbar. The reaction is preferably carried out in the presence of one under reaction conditions inert solvent carried out. The above can be used as such. The reaction temperatures can be varied within a relatively wide range, it is preferable to work between +50 and + 1200C. As acid-binding agents are the above can also be used.

Die Thioglykolsäureanilide gemäß Formel (11) lassen sich nach literaturbekannten Methoden herstellen. Die Halogenphosphorverbindungen der Formel III sind bekannt und nach üblichen Methoden leicht zugänglich. The thioglycolic anilides according to formula (11) can be according to the literature Establish methods. The halophosphorus compounds of the formula III are known and easily accessible by conventional methods.

b) Das Verfahren b) verläuft in der ersten Stufe (Umsetzung von III mit IV) entsprechend dem Verfahren a). Das Zwischenpro dukt der Formel V kann ohne Isolierung, d.h. in einem Eintopfverfahren, direkt der Aminolyse unterworfen werden, wobei man bei Temperaturen von 0- - 1500C arbeiten kann. Die Reaktionstemperatur richtet sich dabei nach der Reaktionsfähigkeit des Restes OR4; aktivierte Ester wie z.B. Phenylester, reagieren bereits bei niederer Temperatur.b) Process b) takes place in the first stage (implementation of III with IV) according to procedure a). The intermediate product of Formula V can be used without Isolation, i.e. subjected directly to aminolysis in a one-pot process, where you can work at temperatures of 0-1500C. The reaction temperature depends on the reactivity of the residue OR4; activated esters such as phenyl esters, react even at low temperatures.

Die erfindungsgemäßen Mittel zeigen eine gute herbizide Wirksamkeit gegen ein breites Spektrum von wirtschaftlich wichtigen Schadgräsern, mit zusätzlicher Wirkung auf breitblättrige Unkräuter. Dabei sind jedoch die Verbindungen gegen die Kulturpflanzen in der als herbizid wirksamen Dosierung out vertrtglich, so daß sie zur Bekämpfung grasartiger und breitblättriger Unkräuter in vielen wichtigen Großkulturen eingesetzt werden können.The agents according to the invention show good herbicidal activity against a wide range of economically important grass weeds, with additional Effect on broad-leaved weeds. However, the connections are against the Crop plants in the herbicidally effective dosage out tolerated, so that they for combating grassy and broad-leaved weeds in many important large-scale crops can be used.

Man kann mit den erfindungegcmäßen Mitteln z.B. Ackerfue}lsschs7anz und Klettenlabkraut in Getreide, Hühnerhirse in Mais und Borstenhirse in Soja- oder Baumwollkulturen mit Erfolg bekämpfen, ohne daß die Kulturpflanze geschädigt wird.With the means according to the invention one can e.g. and burdock in cereals, chicken millet in corn, and millet in soybean or Fight cotton crops with success without damaging the crop.

In anderen Kulturarten wie z.B. Reis werden grasartige Unkräuter wie Hühnerhirse und Seggen (Cyperusarten; unter Schonung der Kulturpflanzen gut vernichtet. Die neuen Mittel der Formel (I) sind in ihrer Unkrautwirkung herkömmlichen Mitteln wie z.B.In other crops such as rice, grassy weeds such as Chicken millet and sedges (Cyperus species; destroyed well with care for the cultivated plants. The new agents of the formula (I) are conventional agents in terms of their weed effect such as.

Propachlor u. a. in von Unkraut befallenen Feldern überlegen.Propachlor et al. superior in weed fields.

Die erfindungsgemäßen Mittel enthalten die Wirkstoffe der Formel I im allgemeinen zu 2 - 95 Gew.-%. Sie können als benetzbare Pulver, emulgierbare Konzentrate, versprühbare Lösungen, Stäubemittel oder Granulate in den üblichen Zubereitungen angewendet werden.The agents according to the invention contain the active ingredients of the formula I. generally from 2 to 95% by weight. They can be used as wettable powder, emulsifiable Concentrates, sprayable solutions, dusts or granules in the usual Preparations are applied.

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, Alkyl- oder Alkyi.-phenyl-sulfonate und Dispergiermittel, z.B. ligninsulfonsaures Natrium, 2,2'-dinaphtylmethan-6.6'-disulfonsaures Natrium, dibutylnaphthalinsulfonsaures Natrium oder auch olevlmE-thvltaurinsaures Natrium enthalten.Wettable powders are preparations that can be uniformly dispersed in water, which, in addition to the active ingredient, apart from a diluent or inert substance, also wetting agents, e.g. polyoxyethylated alkylphenols, polyoxyethylated oleyl or stearylamines, alkyl or alkyl phenyl sulfonates and dispersants, e.g. sodium lignin sulfonic acid, Sodium 2,2'-dinaphthylmethane-6,6'-disulfonic acid, dibutylnaphthalenesulfonic acid Contain sodium or olevlmE-thvltaurinsauresodium.

Emulqierbare 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 such as butanol, cyclohexanone, dimethylformamide, xylene or also higher-boiling aromatics.

Um in Wasser gute Suspensionen oder Emulsionen zu erreichen, werden weiterhin Netzmittel aus der oben genannten Reihe zugesetzt.In order to achieve good suspensions or emulsions in water wetting agents from the series mentioned above were also 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 substances, e.g. 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 Treibmittei 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 For example, a mixture of chlorofluorocarbons can be used as the propellant.

Granulate können entweder durch Verdüsen des Wirkstoffes auf adsorptionsfähiges, granuliertes Inertmaterial hergestellt werden oder durch Aufbringen von Wirkstoffkonzentraten mittels Klebemitteln, z.B. Polyvinylalkohol, polyacrylsaurem Natrium oder auch Mineralölen auf die Oberfläche von Trägerstoffen, wie Sand, Kaolinite, oder von granuliertem Inertmaterial. Auch können geeignete Wirkstoffe in der für die Herstellung von Düngemittelgranalien üblichen Weise - gewünschtenfalls in Mischung mit Düngemitteln - hergestellt werden.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. Suitable active ingredients can also be used in the production of fertilizer granules the usual way - if desired in a mixture with fertilizers - are produced.

Bei herbiziden Mitteln können die Konzentrationen der Wirkstoffe in den handelsüblichen Formulierungeii verschieden sein.In the case of herbicidal agents, the concentrations of the active ingredients can be in be different from the formulations customary in the trade.

In benetzbaren Pulvern variiert die Wirkstoffkonzentration z.B.In wettable powders the active ingredient concentration varies e.g.

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 meistens 5 - 20 % an Wirkstoff, versprühbare Lösungen etwa 2 - 20 %. Bei Granulaten hängt der Wirkstoffgehalt zum Teil davon ab, oh die wirksame Verbindung flüssig oder fest vorliegt und welche Granulierhilfsmittel, Füllstoffe usw. verwendet werden.between about 10% and 95%, the remainder being those given above Formulation additives. In the case of emulsifiable concentrates, the active ingredient concentration is about 10% to 80%. Dusty Formulations mostly contain 5 - 20% active ingredient, sprayable solutions around 2 - 20%. In the case of granules, it hangs the active ingredient content partly depends on whether the active compound is liquid or solid and which granulating aids, fillers, etc. are used.

Zur Anwendung werden die handelsüblichen Konzentrate qeclebenenfalls in üblicher Weise verdünnt, z.B. bei benetzbaren Pulvern und emulgierbaren Konzentraten mittels Wasser. Staubförmige und granulierte Zubereitunqen sowie versprühbare Lösungen werden vor der Anwendung nicht mehr mit weiteren inerten Stoffen verdünnt. Mit den äußeren Bedingungen wie Temperatur, Feuchtigkeit u. a. variiert die erforderliche Aufwandmenge. Sie beträgt im allgemeinen etwa 0,1 - 10 kg/ha, vorzugsweise etwa 0,15 bis 2,5 kg/ha Wirkstoff. Der erfindungsgemäße Wirkstoff kann mit anderen Herbiziden und Bodeninsektiziden kombiniert werden.The commercially available concentrates are used for application if necessary diluted in the usual way, e.g. in the case of wettable powders and emulsifiable concentrates by means of water. Dust-like and granulated preparations as well as sprayable solutions are no longer diluted with other inert substances before use. With the external conditions such as temperature, humidity, etc. varies the required Application rate. It is generally about 0.1-10 kg / ha, preferably about 0.15 to 2.5 kg / ha active ingredient. The active ingredient according to the invention can be used with other herbicides and soil insecticides can be combined.

Als bekannte Herbizide, die sich für eine Kombination mit dem beanspruchten neuen Produkt eignen, kommen z.B. die nachfolgenden unter ihren "common names" bzw. chemischen Bezeichnungen aufgeführten Verbindungen in Frage: Harnstoff-Derivate: Linuron, Monolinuron, Chlortoluron, Isoproturon, Metoxuran, Fluometuron, Diuron, Metabenzthiazuron; Triazin-Derivate: Simazin, Atrazin, Ametryn, Prometryn, Desmetryn, Methoprotryn, Metribuzin; Urazil-Derivate: Lenazil, Bromazil; Phenoxy-alkancarbonsäure: 2,4-D, MCPA, Dichlorprop, Mecoprop, 2,4-DB, TBA; Carbaminsäure-Deriva te: Barban, Phenmedipham, Diallat, Triallat, Vernolat, Benthiocarb, Sweb; Dinitrophenol-Derivate: DNOC, DNBP(Dinoseb), Dinoterb und deren Ester bzw. Salze; Chlorierte aliphatische Säuren: TCA, Dalapon; Amide: Diphenamid, Isocarbomid; Anilide: Propanil, Solan, Monalide, Alachlor, Propachlor, Butachlor; Aniline: Trifluralin, Nitralin, Orvzalin, Dinitramin; Dipyridylium-Verbindungen: Paraquat, Diquat; Andere Wirkstoffgruppen : Dichlobenzil, Ioxynil, Cyanazin, Pyrazon, Bromofenoxim, Chlorthalmethyl, Benzoylpropäthyl, Chlorphenpropmethyl, MSXA, DSMA, Nitrofen, Flurenol, Bentazon, Fluorodifen Eine andere Anwendungsform des vorliegenden Wirkstoffes besteht in seiner Mischung mit Düngemitteln, wodurch düngende und zugleich herbizide Mittel erhalten werden.As well-known herbicides that are suitable for a combination with the claimed are suitable for new products, e.g. the following ones come under their "common names" or Chemical names listed compounds in question: Urea derivatives: Linuron, Monolinuron, Chlortoluron, Isoproturon, Metoxuran, Fluometuron, Diuron, Metabenzthiazuron; Triazine derivatives: Simazine, Atrazine, Ametryn, Prometryn, Desmetryn, Methoprotryn, metribuzin; Urazil derivatives: lenazil, bromazil; Phenoxyalkanecarboxylic acid: 2,4-D, MCPA, dichloroprop, mecoprop, 2,4-DB, TBA; Carbamic acid derivatives: Barban, Phenmedipham, diallate, triallate, vernolate, benthiocarb, sweb; Dinitrophenol derivatives: DNOC, DNBP (Dinoseb), Dinoterb and their esters or salts; Chlorinated aliphatic Acids: TCA, dalapon; Amides: diphenamide, isocarbomide; Anilides: propanil, solane, Monalide, alachlor, propachlor, butachlor; Aniline: Trifluralin, Nitralin, Orvzalin, Dinitramine; Dipyridylium compounds: Paraquat, Diquat; Other drug groups : Dichlobenzil, ioxynil, cyanazine, pyrazone, bromofenoxime, chlorothalmethyl, benzoylpropäthyl, Chlorophenpropmethyl, MSXA, DSMA, Nitrofen, Flurenol, Bentazon, Fluorodifen One Another application form of the present active ingredient consists in its mixture with Fertilizers, whereby fertilizing and at the same time herbicidal agents are obtained.

FORMULIERUNGSBEISPIELE Beispiel A: Ein in Wasser leicht dispergierbares benetzbares Pulver wird erhalten, indem man 25 Gewichtsteile S[N(3-Chlorphenyl)-N-methyl-carbamoylmethyl]-O-äthyl-isopropyl-amido-thiophosphat als Wirkstoff, 64 Gewichtsteile kaolinbaltigen Quarz als Inertstoff.FORMULATION EXAMPLES Example A: One that is readily dispersible in water wettable powder is obtained by adding 25 parts by weight of S [N (3-chlorophenyl) -N-methyl-carbamoylmethyl] -O-ethyl-isopropyl-amido-thiophosphate as an active ingredient, 64 parts by weight of kaolin-containing quartz as an inert substance.

10 Gewichtsteile Ligninsulfonsaures Kalium und 1 Gewichtsteil oleymethyltaurinsäures Natrium als Netz-und Dispergiermittel mischt und in einer Stiftmühle mahlt.10 parts by weight of potassium lignin sulfonic acid and 1 part by weight of olymethyltauric acid Mixes sodium as a wetting and dispersing agent and grinds it in a pin mill.

Beispiel B Ein Stäubemi,ttel, das sich zur Anwendung als Unkrautvertilgungsmittel gut eignet, wird erhalten, indem man 10 Gewichtsteile S[N(3-Chlorphenyl)-N-methyl-carbamoylmethyl O-äthyl-isopropylamido-thiophosphat als Wirkstoff und 90 Gewichtsteile Tallcum als Inertstoff mischt und in einer Schlagmiihle zerkleinert.Example B A dust remedy that can be used as a herbicide well suited, is obtained by adding 10 parts by weight of S [N (3-chlorophenyl) -N-methyl-carbamoylmethyl O-ethyl isopropylamido-thiophosphate as the active ingredient and 90 parts by weight of tallcum as Mixes inert substance and crushes it in a hammer mill.

Beispiel C Ein emulgierbares Konzentrat besteht aus 15 Gewichtsteilen S[N(3-Chlorphenyl)-N-methyl-carbamoylmethyl] -O-äthyl-isopropylamido-thiophosphat, 75 Gewichtsteilen Cyclohexanon als Lösungsmittel und 10 Gewichtsteilen oxäthyliertes Nonylphenyl (10 Ae0> als Emulgator.Example C An emulsifiable concentrate consists of 15 parts by weight S [N (3-chlorophenyl) -N-methyl-carbamoylmethyl] -O-ethyl-isopropylamido-thiophosphate, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxethylated Nonylphenyl (10 Ae0> as an emulsifier.

Beispiel D: Ein Granulat besteht z.B. aus etwa 2 - 15 Gewichtsteilen S[N(3-Chlorphenyl)-N-methyl-carbamoylmethyl]-O-äthyl-isopropylamido-thiophosphat und inerten Granulatträgermaterialien, wie z.B. Attapulgi Bimsgranulat und Quarzsand.Example D: A granulate consists e.g. of about 2-15 parts by weight S [N (3-chlorophenyl) -N-methyl-carbamoylmethyl] -O-ethyl-isopropylamido-thiophosphate and inert granulate carrier materials such as Attapulgi pumice granulate and quartz sand.

HERSTELLUNGSBEISPIELE Allgemeine Vorschrift: Zu einer Lösung oder Suspension von 0,10 - 0,11 Ilol eines Ammoniumsalzes einer Phosphorverbindung der Formel III (R5 = SNH4) ill 200 ml Glykoldimethyläther gibt man bei Raumtemperatur unter Rühren 0,1 jiel eines Chloracetanilids der Formel II (R4 = ci). all rührt ca. 3 - 5 Stunden bei 50° C, saugt vom ausgefallenen Salz ab, verdünnt das Filtrat mit ca. 400 ml Benzol, wäscht die organische Phase grundlich mit Wasser und trocknet über Natriumsulfat. Nach dem ADdestillieren des Lösungsmittels hinterbleiben die Verfahrensprodukte als Oele, die zu.a Teil beim Anreiben kristallisieren.PREPARATION EXAMPLES General rule: To a solution or Suspension of 0.10-0.11 Ilol of an ammonium salt of a phosphorus compound of Formula III (R5 = SNH4) ill 200 ml of glycol dimethyl ether are added at room temperature 0.1 μl of a chloroacetanilide of the formula II (R4 = ci) with stirring. all stirs approx. 3 - 5 hours at 50 ° C, sucks off the precipitated salt, dilutes the filtrate with approx. 400 ml of benzene, wash the organic phase thoroughly with water and dry over sodium sulfate. After the solvent has been distilled off, the Process products as oils, some of which crystallize when rubbed.

Nach dem oben angegebenen Verfahren wurden die in der folgenden Tabelle aufgeführten Verbindungen der Formel I getrolmen, deren Zusammensetzung durch Elementaranalyse bestätigt wurde und die durch Brechungsindex und/oder Schmelzpunkt charakterisiert sind: Tabelle Beispiel Nr. (R)n R1 R2 R3 X Fp bzw. nD 1 H -CH(CH3)2 -NH-CH3 -C2H5 O Fp. 67-68° 2 4-F -CH(CH3)2 -N(CH3)2 -C2H5 O nD23: 1.5192 3 2-Cl -CH3 -NH-CH3 -C2H5 O nD24: 1.5534 4 2-Cl -CH3 -NH-CH(CH3)2 -C2H5 O nD24: 1.5473 5 2-Cl -CH3 -NH-CH2-CH=CH2 -C2H5 O nD24: 1.5513 6 2-Cl -CH3 -NH-C4H9(n) -C2H5 O nD24: 1.5383 7 3-Cl -CH3 -NH-CH3 -C2H5 O nD24: 1.5548 8 3-Cl -CH3 -NH-CH(CH3)2 -C2H5 O nD24: 1.5383 9 3-Cl -CH3 -NH-CH2-CH=CH2 -C2H5 O nD24: 1.5545 10 3-Cl -CH3 -NH-C4H9 (n) -C2H5 O nD24: 1.5410 11 4-Cl -CH3 -NH-CH3 -C2H5 O -- 12 4-Cl -CH3 -NH-CH(CH3)2 -C2H5 O nD24: 1.5192 Tabelle (Fortsetzung) Beispiel Nr. (R)n R1 R2 R3 X Fp bzw. nD 13 4-Cl -C2H5 -N(CH3) -C2H5 O nD24: 1.5403 14 4-Cl -C4H9 (sek) @@@ -C2H5 O nD24: 1.5329 15 4-Cl -C4H9 (sek) -NH-CH(CH3)2 -C2H5 O nD24: 1.5316 16 4-Br -CH(CH3)2 -N(CH3)2 -C2H5 O nD24: 1.5465 17 4-Br -CH3 -NH-CH(CH3)2 -C2H5 O nD24: 1.5412 18 2,3-Cl -CH3 -NH-CH3 -C2H5 O nD24: 1.5585 19 2,3-Cl -CH3 -NH-CH(CH3)2 -C2H5 O nD24: 1.5452 20 2,4-Cl -CH3 -NH-CH3 -C2H5 O nD24: 1.5604 21 2,4-Cl -CH3 -NH-CH(CH3)2 -C2H5 O nD24: 1.5405 22 2,4-Cl -CH3 -NH-CH2-CH=CH2 -C2H5 O nD24: 1.5542 23 2,4-Cl -CH3 -NH-C4H9 (n) -C2H5 O nD24: 1.5447 24 2,4-Cl -CH3 -NH-CH3 -C2H5 O nD24: 1.5645 25 2,5-Cl -CH3 -NH-CH(CH3)2 -C2H5 O nD24: 1.5502 26 2,5-Cl -CH3 -NH-CH2-CH=CH2 -C2H5 O nD24: 1.5597 27 2,5-Cl -CH3 -NH-C4H9 (n) -C2H5 O nD24: 1.5474 Tabelle (Fortsetzung) Beispiel Nr. (R)n R1 R2 R3 X Fp bzw. nD 28 3,4-Cl -CH3 -NH-CH3 -C2H5 O nD24: 1.5620 29 3,4-Cl -CH3 -NH-CH(CH3)2 -C2H5 O nD24: 1.5451 30 3,4-Cl -CH3 -NH-CH(CH3)2 -C2H5 O nD24: 1.5495 31 4-C(CH3)2 -CH(CH3)2 -NH-C4H9 (n) -C2H5 O nD24: 1.5226 32 4-C(CH3)2 -CH(CH3)2 -NH-CH3 -C2H5 O nD24: 1.5270 33 3-CF3 -CH(CH3)2 -NH-CH(CH3)2 -C2H5 O nD24: 1.5180 34 3-CF3 -CH(CH3)2 -NH-CH3 -C2H5 O nD24: 1.4935 35 3-CF3 -CH(CH3)2 -N(CH3)2 -C2H5 O nD24: 1.4953 36 3-CF3 -C4H9 (sek) -NH-CH(CH3)2 -C2H5 O nD24: 1.4994 37 3-CF3 -C4H9 (sek) -NH-CH3 -C2H5 O nD24: 1.4930 38 3-CF3 -C4H9 (sek) -NH-CH(CH3)2 -C2H5 O nD24: 1.4953 39 3-CF3 -C4H9 (sek) -NH-CH2-CH=CH2 -C2H5 O nD24: 1.5047 40 4-Cl -CH(CH3)2 -NH-CH3 -CH3 O -- 41 2-F -CH(CH3)2 -NH-CH(CH3)2 -C2H5 O nD24: 1.5171 42 H H -NH-C3H7 iso -C2H5 O nD30: 1.5666 43 H H -NH-# -C2H5 O Fp. 90-93°C Tabelle (Fortsetzung) Beispiel Nr. (R)n R1 R2 R3 X Fp bzw. nD 45 H H -N#O -C2H5 O nD29: 1.5568 46 H CH3 -N#O -C2H5 O -- 47 3-CH3 C3H7-iso -NH-C4H9 n -C2H5 O nD29: 1.5236 48 4-CH3 -CH(CH3)2 -NH-C4H9 n -C2H5 O Fp. 59-64°C 49 4-CH3 -CH(CH3)2 -NH-CH2-CH=CH2 -C2H5 O nD29: 1.5270 50 2-CH3 -CH(CH3)2 -NH-C3H7-iso -C2H5 O nD32: 1.5180 51 2-CH3 -CH(CH3)2 -NH-CH2-CH=CH2 -C2H5 O nD29: 1.4935 52 2,4-Cl -CH3 -NH-CH(CH3)2 -C2H5 O -- 53 4-Cl -CH(CH3)2 -NH-# -C2H5 O -- 54 3-Cl -CH3 " -C2H5 O nD30: 1.4930 55 3-Cl -CH3 -N# -C2H5 O nD30: 1.4953 56 3,4-Cl -CH3 -NH-C3H7 iso -C2H5 O nD31: 1.5047 Tabelle (Fortsetzung) Beispiel Nr. (R)n R1 R2 R3 X Fp bzw. nD 57 H -CH3 -NHC5H7-iso -C2H5 O nD27: 1.5172 58 3-CH3 -CH(CH3)2 -NHC3H7-iso -C2H5 O nD32: 1.5188 59 3-CH3 -CH(CH3)2 -NH-CH2-CH=CH2 -C2H5 O nD50: 1.5343 60 3-CH3 -CH(CH3)2 -N#O -C2H5 O nD32: 1.5350 61 4-CH3 -CH(CH3)2 -N#O -C2H5 O nD32: 1.5343 62 4-CH3 -CH(CH3)2 -NHC3H7-iso -C2H5 O Fp. 69-71°C 63 2-CH3 -CH(CH3)2 -NHC4H2-iso -C2H5 O nD29: 1.5257 64 2-CH3 -CH(CH3)2 -N#O -C2H5 O nD32: 1.5337 65 3-Cl -CH3 -N#O -C2H5 O nD27: 1.555 66 2,4-Cl -CH(CH3)2 -NH-#H -C2H5 O Fp. 90-94°C 67 2,4-Cl -CH3 -N#O -C2H5 O nD27: 1.5551 Tabelle (Fortsetzung) Beispiel Nr. (R)n R1 R2 R3 X Fp bzw. nD 68 3,4-Cl -CH(CH3)2 -NHC4H9-n -C2H5 O nD29: 1.5402 69 3,4-Cl -CH(CH3)2 -NHC3H7-iso -C2H5 O nD31: 1.5419 70 3-Cl -CH(CH3)2 -NHC3H7-iso -C2H5 O nD31: 1.5350 71 4-Br -CH(CH3)2 -NHC3H7-iso -C2H5 O Fp. 85-86 72 2,5-Cl -CH(CH3)2 -NHC3H7-iso -C2H5 O Fp. 105-105°C 73 4-NO2 -CH(CH3)2 -NHC3H7-iso -C2H5 O Fp. 46-52°C 74 4-NO2 -CH(CH3)2 -NHC4H9-n -C2H5 O Fp. 69-71°C 75 4-NO2 -CH(CH3)2 -NH-CH2-CH=CH2 -C2H5 O nD32: 1.5549 76 4-NO2 -CH(CH3)2 -N#O -C2H5 O nD32: 1.5483 77 4-SCH3 -CH(CH3)2 -NHC3H7-iso -C2H5 O Fp. 81-84°C BIOLOGISCHE BEISPIELE Die biologische Prüfung der erfindungsgemäßen Verbindungen zeigte deren gute herbizide Wirksamkeit gegen ein breites Spektrum von wirtschaftlich wichtigen Schdräsern wie Lolium, Poa, Setaria, Echinochloa u.a. verbunden mit zusätzlicher Wirkung auf breitblattrige Unkräuter. Die erfindungsgemäPen Verbindungen waren gegen viele wichtige Kulturpflanzen in den herbizid wirksamen Dosierungen gut verträglich, so daß sie zur Bekämpfung grasartiger und breitblättriger Unkräuter in diesen Kulturen eingesetzt werden können.The compounds of the formula I listed in the following table, the composition of which was confirmed by elemental analysis and which are characterized by refractive index and / or melting point, were trolled according to the method given above: Table Example No. (R) n R1 R2 R3 X Fp or nD 1 H -CH (CH3) 2 -NH-CH3 -C2H5 O M.p. 67-68 ° 2 4-F-CH (CH3) 2 -N (CH3) 2 -C2H5 O nD23: 1.5192 3 2-Cl -CH3 -NH-CH3 -C2H5 O nD24: 1.5534 4 2-Cl -CH3 -NH-CH (CH3) 2 -C2H5 O nD24: 1.5473 5 2-Cl -CH3 -NH-CH2-CH = CH2 -C2H5 O nD24: 1.5513 6 2-Cl -CH3 -NH-C4H9 (n) -C2H5 O nD24: 1.5383 7 3-Cl -CH3 -NH-CH3 -C2H5 O nD24: 1.5548 8 3-Cl -CH3 -NH-CH (CH3) 2 -C2H5 O nD24: 1.5383 9 3-Cl -CH3 -NH-CH2-CH = CH2 -C2H5 O nD24: 1.5545 10 3-Cl -CH3 -NH-C4H9 (n) -C2H5 O nD24: 1.5410 11 4-Cl -CH3 -NH-CH3 -C2H5 O - 12 4-Cl -CH3 -NH-CH (CH3) 2 -C2H5 O nD24: 1.5192 Table (continued) Example No. (R) n R1 R2 R3 X Fp or nD 13 4-Cl -C2H5 -N (CH3) -C2H5 O nD24: 1.5403 14 4-Cl -C4H9 (sec) @@@ -C2H5 O nD24: 1.5329 15 4-Cl -C4H9 (sec) -NH-CH (CH3) 2 -C2H5 O nD24: 1.5316 16 4-Br -CH (CH3) 2 -N (CH3) 2 -C2H5 O nD24: 1.5465 17 4-Br-CH3 -NH-CH (CH3) 2 -C2H5 O nD24: 1.5412 18 2,3-Cl -CH3 -NH-CH3 -C2H5 O nD24: 1.5585 19 2,3-Cl -CH3 -NH-CH (CH3) 2 -C2H5 O nD24: 1.5452 20 2,4-Cl-CH3 -NH-CH3 -C2H5 O nD24: 1.5604 21 2,4-Cl-CH3 -NH-CH (CH3) 2 -C2H5 O nD24: 1.5405 22 2,4-Cl-CH3 -NH-CH2-CH = CH2 -C2H5 O nD24: 1.5542 23 2,4-Cl-CH3 -NH-C4H9 (n) -C2H5 O nD24: 1.5447 24 2,4-Cl-CH3 -NH-CH3 -C2H5 O nD24: 1.5645 25 2,5-Cl -CH3 -NH-CH (CH3) 2 -C2H5 O nD24: 1.5502 26 2,5-Cl-CH3 -NH-CH2-CH = CH2 -C2H5 O nD24: 1.5597 27 2,5-Cl -CH3 -NH-C4H9 (n) -C2H5 O nD24: 1.5474 Table (continued) Example No. (R) n R1 R2 R3 X Fp or nD 28 3,4-Cl -CH3 -NH-CH3 -C2H5 O nD24: 1.5620 29 3,4-Cl -CH3 -NH-CH (CH3) 2 -C2H5 O nD24: 1.5451 30 3,4-Cl -CH3 -NH-CH (CH3) 2 -C2H5 O nD24: 1.5495 31 4-C (CH3) 2 -CH (CH3) 2 -NH-C4H9 (n) -C2H5 O nD24: 1.5226 32 4-C (CH3) 2 -CH (CH3) 2 -NH-CH3 -C2H5 O nD24: 1.5270 33 3-CF3 -CH (CH3) 2 -NH-CH (CH3) 2 -C2H5 O nD24: 1.5180 34 3-CF3 -CH (CH3) 2 -NH-CH3 -C2H5 O nD24: 1.4935 35 3-CF3 -CH (CH3) 2 -N (CH3) 2 -C2H5 O nD24: 1.4953 36 3-CF3 -C4H9 (sec) -NH-CH (CH3) 2 -C2H5 O nD24: 1.4994 37 3-CF3 -C4H9 (sec) -NH-CH3 -C2H5 O nD24: 1.4930 38 3-CF3 -C4H9 (sec) -NH-CH (CH3) 2 -C2H5 O nD24: 1.4953 39 3-CF3 -C4H9 (sec) -NH-CH2-CH = CH2 -C2H5 O nD24: 1.5047 40 4-Cl -CH (CH3) 2 -NH-CH3 -CH3 O - 41 2-F-CH (CH3) 2 -NH-CH (CH3) 2 -C2H5 O nD24: 1.5171 42 HH -NH-C3H7 iso -C2H5 O nD30: 1.5666 43 HH -NH- # -C2H5 O m.p. 90-93 ° C Table (continued) Example No. (R) n R1 R2 R3 X Fp or nD 45 HH -N # O -C2H5 O nD29: 1.5568 46 H CH3 -N # O -C2H5 O - 47 3-CH3 C3H7-iso -NH-C4H9 n -C2H5 O nD29: 1.5236 48 4-CH3 -CH (CH3) 2 -NH-C4H9 n -C2H5 O m.p. 59-64 ° C 49 4-CH3 -CH (CH3) 2 -NH-CH2-CH = CH2 -C2H5 O nD29: 1.5270 50 2-CH3 -CH (CH3) 2 -NH-C3H7-iso -C2H5 O nD32: 1.5180 51 2-CH3 -CH (CH3) 2 -NH-CH2-CH = CH2 -C2H5 O nD29: 1.4935 52 2,4-Cl -CH3 -NH-CH (CH3) 2 -C2H5 O - 53 4-Cl -CH (CH3) 2 -NH- # -C2H5 O - 54 3-Cl -CH3 "-C2H5 O nD30: 1.4930 55 3-Cl -CH3 -N # -C2H5 O nD30: 1.4953 56 3,4-Cl -CH3 -NH-C3H7 iso -C2H5 O nD31: 1.5047 Table (continued) Example No. (R) n R1 R2 R3 X Fp or nD 57 H -CH3 -NHC5H7-iso -C2H5 O nD27: 1.5172 58 3-CH3 -CH (CH3) 2 -NHC3H7-iso -C2H5 O nD32: 1.5188 59 3-CH3 -CH (CH3) 2 -NH-CH2-CH = CH2 -C2H5 O nD50: 1.5343 60 3-CH3 -CH (CH3) 2 -N # O -C2H5 O nD32: 1.5350 61 4-CH3 -CH (CH3) 2 -N # O -C2H5 O nD32: 1.5343 62 4-CH3 -CH (CH3) 2 -NHC3H7-iso -C2H5 O m.p. 69-71 ° C 63 2-CH3 -CH (CH3) 2 -NHC4H2-iso -C2H5 O nD29: 1.5257 64 2-CH3 -CH (CH3) 2 -N # O -C2H5 O nD32: 1.5337 65 3-Cl -CH3 -N # O -C2H5 O nD27: 1.555 66 2,4-Cl -CH (CH3) 2 -NH- # H -C2H5 O m.p. 90-94 ° C 67 2,4-Cl -CH3 -N # O -C2H5 O nD27: 1.5551 Table (continued) Example No. (R) n R1 R2 R3 X Fp or nD 68 3,4-Cl -CH (CH3) 2 -NHC4H9-n -C2H5 O nD29: 1.5402 69 3,4-Cl -CH (CH3) 2 -NHC3H7-iso -C2H5 O nD31: 1.5419 70 3-Cl -CH (CH3) 2 -NHC3H7-iso -C2H5 O nD31: 1.5350 71 4-Br -CH (CH3) 2 -NHC3H7-iso -C2H5 O m.p. 85-86 72 2,5-Cl -CH (CH3) 2 -NHC3H7-iso -C2H5 O m.p. 105-105 ° C 73 4-NO2 -CH (CH3) 2 -NHC3H7-iso -C2H5 O m.p. 46-52 ° C 74 4-NO2 -CH (CH3) 2 -NHC4H9-n -C2H5 O m.p. 69-71 ° C 75 4-NO2 -CH (CH3) 2 -NH-CH2-CH = CH2 -C2H5 O nD32: 1.5549 76 4-NO2 -CH (CH3) 2 -N # O -C2H5 O nD32: 1.5483 77 4-SCH3 -CH (CH3) 2 -NHC3H7-iso -C2H5 O M.p. 81-84 ° C BIOLOGICAL EXAMPLES The biological testing of the compounds according to the invention showed their good herbicidal activity against a broad spectrum of economically important weeds such as Lolium, Poa, Setaria, Echinochloa and others combined with an additional effect on broad-leaved weeds. The compounds according to the invention were well tolerated by many important crop plants in the herbicidally effective dosages, so that they can be used in these crops for combating grass-like and broad-leaved weeds.

Beispiel I: (Vorauflau-Verfahren) Die beanspruchten Verbindungen wurden in verschiedenen Dosierungen auf Töpfe gesprüht, in denen Samen wichtiger Unkräuter ausgesät worden waren. Nach dieser Behandlung wurden die Versuchstöpfe im Gewächshaus aufgestellt und die Wirksamkeit der Verbindungen zu verschiedenen Zeiten nach der Applikation nach dem üblichen EWRC-Schema bonitiert.Example I: (pre-emergence method) The claimed compounds were sprayed in different doses on pots in which seeds of important weeds had been sown. After this treatment, the test pots were placed in the greenhouse established and the effectiveness of the compounds at different times according to the Application rated according to the usual EWRC scheme.

Bonitierungsschema nach BOLLE (Nachrichtenblatt des Deutschen Pflanzenschutzdienstes 16, 1964, 92 - 94).Rating scheme according to BOLLE (news sheet of the German Plant Protection Service 16, 1964, 92-94).

Schadwirkung in % an Wertzahl Unkräutern Kulturpflanzen 1 100 0 2 97,5 biß <100 > 0 bis 2,5 3 95 bis<97,5 > 2,5 bis 5 4 90 bis <95 ' > 5 bis 10 5 85 bis <90 > 10 bis 15 6 75 bis<85 >15 bis 25 7 65 bis <75 > 25 bis 35 8 32,5 bis <65 >35 bis 67,5 0 0 bis 932,5 >67,5 bis 100 Die Endbonitur ca. 4 Wochen nach der Behandlung se gte, daß die erfindungsgemäßen Verbindungen eine sehr gute herbizide Effektivität gegen viele wirtschaflich wichtige Schadgräser besitzen und auch dikotyle Unkräuter in feldüblichen Dosierlln-en sehr gut bekämpfen. Als Vergleichsmittel dienten verschiedene Phosphoräureester. Harmful effect in% of weeds value number Cultivated plants 1 100 0 2 97.5 to <100> 0 to 2.5 3 95 to <97.5> 2.5 to 5 4 90 to <95 '> 5 to 10 5 85 to <90> 10 to 15 6 75 to <85> 15 to 25 7 65 to <75> 25 to 35 8 32.5 to <65> 35 to 67.5 0 0 to 932.5> 67.5 to 100 The final rating About 4 weeks after the treatment, it was found that the compounds according to the invention have a very good herbicidal effectiveness against many economically important grass weeds and also control dicotyledon weeds very well in doses customary in the field. Various phosphoric acid esters were used as comparison agents.

sowie (Propachlor) Die erfindungsgemäßen Verbindungen waren diesen sowohl in der herbiziden Wirksamkeit gegen Schadräser sowie in der beachtlichen Nebenwirkung gegen breitblättrige Unkräuter überlegen (Tab. 1).as (Propachlor) The compounds according to the invention were superior to these both in their herbicidal activity against harmful grasses and in the considerable side effect against broad-leaved weeds (Tab. 1).

TABELLE I a: Vorauflaufwirkung gegen Ungräser Verbindung kg AS Alopecu- Setaria Poa Poa Lolium Echino- gemäß Bei- /ha rus annua trivialis chloa spiel Nr. 8 2,5 2 1 1 1 1 1 0,6 7 5 4 1 7 6 0,15 9 9 1 9 9 8 25 2,5 1 1 2 1 1 1 0,6 6 5 9 1 2 1 0,15 9 8 1 7 9 8 26 2,5 1 1 1 1 1 1 0,6 5 2 7 1 1 2 0,15 9 8 1 6 9 8 28 2,5 2 1 3 1 1 1 0,6 8 1 8 3 7 2 0,15 9 7 1 9 9 9 A 2,5 4 1 2 1 8 1 0,6 8 2 9 3 9 1 0,15 9 8 1 5 9 9 B 2,5 4 3 8 1 8 4 0,6 8 7 9 5 9 8 0,15 9 9 1 9 9 9 C 2,5 2 1 1 1 8 1 0,6 8 8 8 1 9 7 0,15 9 9 9 9 9 9 D 2,5 9 2 6 4 8 3 0,6 9 8 9 7 9 8 0,15 9 9 9 9 9 9 TABELLE I b: Vorauflaufwirkung gegen breitblättrige Unkräuter Verbindung gemäß kg Sinapis Galium Cheno- Chrysan- Stellaria Amaranthus Beispiel Nr. As/ha podium themum 8 2,5 7 8 6 1 1 1 0,6 8 9 8 8 8 5 0,15 9 9 9 9 9 7 25 2,5 2 4 4 1 1 1 0,6 8 7 8 6 9 5 0,15 9 8 9 9 9 5 26 2,5 6 1 1 2 1 1 0,6 8 8 6 8 8 2 0,15 9 9 6 9 9 3 28 2,5 8 8 2 5 1 1 0,6 9 9 7 9 8 8 0,15 9 9 9 9 9 9 A 2,5 8 9 8 8 9 9 0,6 9 9 9 9 9 9 0,15 9 9 9 9 9 9 B 2,5 8 8 8 8 3 7 0,6 9 9 9 9 8 9 0,15 9 9 9 9 9 9 C 2,5 9 7 8 8 8 6 0,6 9 9 9 9 9 9 0,15 9 9 9 9 9 9 Beispiel II: (Vorauflauf-Verfahren) In ähnlicher Weise wie in Beispiel 1 wurden erfindungsgemäj3e Substanzen an Kulturpflanzen geprüft. Wie in Tabelle II ersichtlich wurde, werden in Dosierungen von 0,6 bis 2,5 Kg/ha zahlreiche in der landwirtschaftlichen und gärtnerischen Praxis wichtige Kulturen geschont. Es ist also möglich, z.B.TABLE I a: Pre-emergence effect against grass weeds Compound kg AS Alopecu- Setaria Poa Poa Lolium Echino- according to Bei- / ha rus annua trivialis chloa game no. 8 2.5 2 1 1 1 1 1 0.6 7 5 4 1 7 6 0.15 9 9 1 9 9 8 25 2.5 1 1 2 1 1 1 0.6 6 5 9 1 2 1 0.15 9 8 1 7 9 8 26 2.5 1 1 1 1 1 1 0.6 5 2 7 1 1 2 0.15 9 8 1 6 9 8 28 2.5 2 1 3 1 1 1 0.6 8 1 8 3 7 2 0.15 9 7 1 9 9 9 A 2.5 4 1 2 1 8 1 0.6 8 2 9 3 9 1 0.15 9 8 1 5 9 9 B 2.5 4 3 8 1 8 4 0.6 8 7 9 5 9 8 0.15 9 9 1 9 9 9 C 2.5 2 1 1 1 8 1 0.6 8 8 8 1 9 7 0.15 9 9 9 9 9 9 D 2.5 9 2 6 4 8 3 0.6 9 8 9 7 9 8 0.15 9 9 9 9 9 9 TABLE I b: Pre-emergence activity against broad-leaved weeds Compound according to kg Sinapis Galium Cheno- Chrysan- Stellaria Amaranthus Example No. As / ha podium themum 8 2.5 7 8 6 1 1 1 0.6 8 9 8 8 8 5 0.15 9 9 9 9 9 7 25 2.5 2 4 4 1 1 1 0.6 8 7 8 6 9 5 0.15 9 8 9 9 9 5 26 2.5 6 1 1 2 1 1 0.6 8 8 6 8 8 2 0.15 9 9 6 9 9 3 28 2.5 8 8 2 5 1 1 0.6 9 9 7 9 8 8 0.15 9 9 9 9 9 9 A 2.5 8 9 8 8 9 9 0.6 9 9 9 9 9 9 0.15 9 9 9 9 9 9 B 2.5 8 8 8 8 3 7 0.6 9 9 9 9 8 9 0.15 9 9 9 9 9 9 C 2.5 9 7 8 8 8 6 0.6 9 9 9 9 9 9 0.15 9 9 9 9 9 9 Example II: (Pre-emergence method) In a manner similar to that in Example 1, substances according to the invention were tested on crop plants. As can be seen in Table II, numerous crops important in agricultural and horticultural practice are spared in doses of 0.6 to 2.5 kg / ha. So it is possible, for example

Alopecurus und Galium in Getreide, Echinochloa in Mais, Setaria in Soj oder baumwolle u.a. zu bekämpfen.Alopecurus and Galium in cereals, Echinochloa in maize, Setaria in To combat soy or cotton, etc.

TABELLE II: Wirkung auf Kulturpflanzen in Vorauflauf-Verfahren Bei- kg/ha Weizen Reis Zucker- Raps Gurke Soja Bohne Baum- Tomate Möhre Mais spiel rübe 8 2,5 2 1 1 1 1 1 1 1 1 1 2 0,6 1 1 1 1 1 1 1 1 1 1 1 25 2,5 3 2 1 1 1 1 1 1 1 1 3 0,6 1 1 1 1 1 1 1 1 1 1 2 26 2,5 4 3 1 1 1 1 1 1 1 1 3 0,6 1 1 1 1 1 1 1 1 1 1 2 28 2,5 2 2 1 1 1 1 1 1 1 1 3 0,6 1 1 1 1 1 1 1 1 1 1 1 TABLE II: Effect on pre-emergence crops At- kg / ha Wheat Rice Sugar Rape Cucumber Soy Bean Tree Tomato Carrot Corn game turnip 8 2.5 2 1 1 1 1 1 1 1 1 1 2 0.6 1 1 1 1 1 1 1 1 1 1 1 25 2.5 3 2 1 1 1 1 1 1 1 1 3 0.6 1 1 1 1 1 1 1 1 1 1 2 26 2.5 4 3 1 1 1 1 1 1 1 1 3 0.6 1 1 1 1 1 1 1 1 1 1 2 28 2.5 2 2 1 1 1 1 1 1 1 1 3 0.6 1 1 1 1 1 1 1 1 1 1 1

Claims (4)

PATENTANSPRÜCHE: 1. Verfahren zur Herstellung von Verbindungen der allgemeinen Formel worin R = gleiche oder verschiedene Substituten aus der Gruppe Halogen, (C1-C6)-Alkyl, (C1-C3)-Halogenalkyl, (C1-C2)-Alkoxy, CN, SO2CH3, SO2-NH2 oder SCH3, R1 = Wasserstoff oder (C1-C6), Alkyl, R3 = (C1-C6)-Alkyl, R2 = (C1-C6)-Alkylamino, (C1-C6)-Alkenylamino, N,N-Di-(C1-C6)-alkylamino, (C5-C8)-Cycloalkylamino oder einen gesättigten N-Heterocyclus mit insgesamt 4 - 8 C-Atomen, von denen 1-2 sich in der Seitenkette befinden können und wobei eine Ring-CH -Gruppe auch durch Sauerstoff oder Schwefel ersetzt sei kann, X = Sauerstoff oder Schwefel, sowie n = 0 oder eine ganze Zahl von 1-3 bedeuten.PATENT CLAIMS: 1. Process for the preparation of compounds of the general formula where R = identical or different substituents from the group consisting of halogen, (C1-C6) -alkyl, (C1-C3) -haloalkyl, (C1-C2) -alkoxy, CN, SO2CH3, SO2-NH2 or SCH3, R1 = hydrogen or (C1-C6), alkyl, R3 = (C1-C6) -alkyl, R2 = (C1-C6) -alkylamino, (C1-C6) -alkenylamino, N, N-di- (C1-C6) -alkylamino, (C5-C8) -Cycloalkylamino or a saturated N-heterocycle with a total of 4 - 8 C atoms, of which 1-2 can be in the side chain and where a ring CH group can also be replaced by oxygen or sulfur, X = oxygen or sulfur, and n = 0 or an integer from 1-3. 2. Verfahren zur EIerstellung von Verbindungen der Formel 1, dadurch gekennzeichnet, daß man a) Verbindungen der Formel mit Phosphorverbindungen der Formel worin jeweils eineL der Reste A und B Halogen, insbesondere Chlor oder Brom, und der andere die SY-Gruppe bedeutet, in welcher Y Wasserstoff oder eiii Metallkation darstellt, gegebenenfalls in Gegenwart eines säurebindenden Mittels, oder b) zunächst Verbindungen der Formel IV mit Verbiiidungen der Formel III umsetzt und die erhaltenen Zwischenprodukte der Formel V durch Umsetzuny mit AnilineSer Formel VI in die Verbindungen der Formel I überführt worin R4 bevorzugt niederes Alkyl oder Phenyl bedeutet.2. A process for preparing compounds of the formula 1, characterized in that a) compounds of the formula with phosphorus compounds of the formula where in each case one of the radicals A and B 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, or b) initially compounds of the formula IV with Verbiiidungen of the formula III and the intermediate products of the formula V by reacting with AnilineSer Formula VI converted into the compounds of the formula I in which R4 is preferably lower alkyl or phenyl. 3. Herbizide Mitte, gekennzeichnet durch einen Gehalt an einer Verbindung der Formel I als Wirkstoff.3. Herbicidal middle, characterized by a content of a compound of formula I as an active ingredient. 4. Verwendung von Verbindungen der Formel I zur Bekämpfung unerwünschten Bilanzenwuchses.4. Use of compounds of the formula I for combating undesirable Balance sheet growth.
DE19762633159 1976-02-04 1976-07-23 Phosphorus-containing compounds, processes for their preparation, and herbicidal compositions containing these compounds Expired DE2633159C2 (en)

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DE19762633159 DE2633159C2 (en) 1976-07-23 1976-07-23 Phosphorus-containing compounds, processes for their preparation, and herbicidal compositions containing these compounds
NL7700930A NL7700930A (en) 1976-02-04 1977-01-28 PLANT PROTECTION PRODUCT.
BG7742074A BG28980A4 (en) 1976-02-04 1977-01-31 Nematocide means
BG7735295A BG27723A3 (en) 1976-02-04 1977-01-31 Herbicide means
BG7942073A BG28979A4 (en) 1976-02-04 1977-01-31 Insecticide 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
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
DD7700197194A DD129105A5 (en) 1976-02-04 1977-02-02 PROCESS FOR THE PREPARATION OF NEW THIOPHOSPHATES
AT64177A AT355860B (en) 1976-02-04 1977-02-02 PEST CONTROL
FI770368A FI770368A (en) 1976-02-04 1977-02-02
NZ183238A NZ183238A (en) 1976-02-04 1977-02-02 Organophosphorus amides and herbicidal,insecticidal,acaricidal and nematocidal compositions
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
GB4194/77A GB1565894A (en) 1976-02-04 1977-02-02 Pesticidal organic phosphorus compounds processes for their preparation and compositions containing them
RO7789255A RO70320A (en) 1976-02-04 1977-02-02 PROCESS FOR OBTAINING COMPOUNDS OF THIOPHOSPHORIC ACID
LU76690A LU76690A1 (en) 1976-02-04 1977-02-02
CH125277A CH631721A5 (en) 1976-02-04 1977-02-02 Pesticides.
PH19410A PH12483A (en) 1976-02-04 1977-02-02 Pesticidal thionophosphonic acid amides
AU21907/77A AU506483B2 (en) 1976-02-04 1977-02-03 Thiophosphate derivatives
IE226/77A IE44595B1 (en) 1976-02-04 1977-02-03 Pesticidal organic phosphorus compounds, processes for theior preparation and compositions containing them
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
GR52705A GR70331B (en) 1976-02-04 1977-02-03
FR7702989A FR2340324A1 (en) 1976-02-04 1977-02-03 ORGANOPHOSPHORUS COMPOUNDS AND PESTICIDAL PRODUCTS WHICH CONTAIN IT
HUHO001956 HU184138B (en) 1976-04-23 1977-02-03 Plant protective composition containing thiophosphoric acid est er-amide derivatives and process for preparing the active substances
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
JP52010342A JPS6013039B2 (en) 1976-02-04 1977-02-03 plant protection agent
CA271,007A CA1088065A (en) 1976-02-04 1977-02-03 Pesticidal agents
YU00284/77A YU28477A (en) 1976-02-04 1977-02-03 Process for preparing thiophosphoric acid derivatives
CS77752A CS199286B2 (en) 1976-02-04 1977-02-04 Fungicides,insecticides,acaricides,nematocides and herbicides and method of producing active compounds
MX775415U MX4478E (en) 1976-02-04 1977-02-04 IMPROVED PROCEDURE FOR OBTAINING ACETANILIDOTIOFOSFATO DERIVATIVES
OA56060A OA05558A (en) 1976-02-04 1977-02-04 Organophosphorus compounds and pesticide products which contain them.
SE7701260A SE427663B (en) 1976-02-04 1977-02-04 PHOSPHORIC ACID EERAMIDS FOR USE AS A PROTECTIVE AGENT
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

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Publication number Priority date Publication date Assignee Title
EP0709368A1 (en) 1994-10-25 1996-05-01 Bayer Ag Herbicidal agent based on the N-(4-fluorphenyl)-N-isopropyl-chloroacetamide and process for its preparation
US5639713A (en) * 1994-10-25 1997-06-17 Bayer Aktiengesellschaft Herbicidal compositions based on N-(4-fluoro-phenyl)-N-isopropyl-chloroacetamide, and process for the preparation of this compound
US5831126A (en) * 1994-10-25 1998-11-03 Bayer Aktiengesellschaft Herbicidal compositions based on N-(4-fluoro-phenyl)-N-isopropyl-chloroacetamide, and process for the preparation of this compound

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