GB2033379A - Fungicidally active acetic acid anilides and their manufacture and use - Google Patents

Fungicidally active acetic acid anilides and their manufacture and use Download PDF

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GB2033379A
GB2033379A GB7932156A GB7932156A GB2033379A GB 2033379 A GB2033379 A GB 2033379A GB 7932156 A GB7932156 A GB 7932156A GB 7932156 A GB7932156 A GB 7932156A GB 2033379 A GB2033379 A GB 2033379A
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oxoperhydro
furyl
acid
anilide
compound
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Bayer Pharma AG
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Schering AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/32—Oxygen atoms
    • C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
    • A01N47/14—Di-thio analogues thereof

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  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Plant Pathology (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Novel acetic acid anilides of the general formula I <IMAGE> (wherein R1 represents H or C1-C4- alkyl, R2 represents aromatic hydrocarbon optionally substituted by one or more substituents selected from C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, Hal, -CF3, -NO2, C1-C4-alkoxycarbonyl and -CN, R3 represents C1-C6-alkyl, halogeno- C1-C6-alkyl, C1-C4-alkoxy-C1-C4- alkyl, C2-C6-alkenyl, C3-C6-alkynyl, C1-C6-alkylcarbonyl or halogeno- C1-C6-alkoxycarbonyl, or represents phenyl or benzyl optionally substituted by one or more substituents selected from Hal, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, -CF3, -NO2 and -NH2, or represents amidino or dimenthylthiocarbamoyl, and X represents O, S, SO or SO2) and acid addition salts of such compounds in which R3 represents amidino, have a fungicidal action against phytopathogenic fungi and accordingly may be made up with suitable carriers into fungicidal preparations and may be used for protecting living plants, crop areas and seeds against such fungi.

Description

SPECIFICATION Fungicidally active acetic acid anilides and their manufacture and use The present invention is concerned with new acetic acid anilides, with processes for the manufacture of these compounds and with the use of these compounds for controlling phytopathogenic fungi.
Agents for controlling phytopathogenic fungi are already known. Agents of this kind known in practice are, for example, tetramethylthiuram disulphide (German Patent Specification No. 642,532) and manganese ethylene bisdithiocarbamate (United States Patent Specification No. 2,504, 404).
The probiem upon which the present invention is based has been to develop new fungicides having a good action against leaf and soil fungi.
This problem is now solved by the new compounds of the present invention, as defined below.
The present invention provides compounds of the general formula I
in which R1 represents a hydrogen atom or a C1-C4-alkyl group, R2 represents an unsubstituted aromatic hydrocarbon group or an aromatic hydrocarbon group substituted by one or more substituents selected from C1-C4-alkyl groups, C1-C4-alkoxy groups, C1-C4-alklthio groups, halogen atoms, trifluoromethyl groups, nitro groups, C1-C4-alkoxycarbonyl groups and cyano groups, R3 represents a C,--Cdalkyl, halogeno-C1-C6-alkyl, C1-C4-alkoxy-C1-C4-alkyl, C2-C6-alkenyl, C3-C6-alkynyl, C1-C6-alkylcarbonyl or halogeno-C1-C6-alkylcarbonyl group, or represents an unsubstituted phenyl or benzyl group or a phenyl orgenzyl group substituted by one or more substituents selected from halogen atoms and C144-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, trifluoromethyl, nitro and amino groups, or represents an amidino or dimethyithiocarbamoyl group, and X represents an oxygen or sulphur atom or a sulphinyl or sulphonyl group, and acid addition salts of such compounds in which R3 represents an amidino group.
When R2 represents an aromatic hydrocarbon group substituted by more than one substituent, these substituents may be the same or different. Similarly, when R3 represents a phenyl or benzyl group substituted by more than one substituent, these may be the same or different.
The compounds of the present invention are, surprisingly, superior to the known agents of the kind mentioned above in their action against phytopathogenic fungi and, in addition, they possess a good plant tolerability and a sufficient duration of action. In the application quantities that come into consideration in practice they do not act phytotoxically and there is, therefore, no risk of plant growth being adversely affected if they are used. Thanks to these advantageous properties, these compounds can therefore be used in agriculture and in horticulture for treating the soil and the ground and can also be applied to foliage.
The compounds of the present invention are distinguished by an outstanding action against a great number of pathogenic fungi, for example Pythium, Phytophthora, Plasmopara, Piricularia and Botrytis.
In contrast to agents that have only a preventive action such as, for example, manganese ethylene bisdithiocarbamate, the compounds of the present invention possess, the exceptional advantage of a curative and systemic action and, therefore, make it possible to control also fungi that have already penetrated into the plants.
The present invention accordingly also provides a fungicidal preparation which comprises one or more compounds selected from compounds of the general formula I and acid addition salts of such compounds in which R3 represents an amidino group, in admixture or conjunction with a suitable carrier.
The present invention further provides a method of protecting a living plant against phytopathogenic fungi, wherein the living plant and/or the area in the vicinity of the living plant is/are treated with one or more compounds selected from compounds of the general formula I and acid addition salts of such compounds in which R3 represents an amidino group.
The present invention further provides a method of protecting a crop area against phytopathogenic fungi, wherein the crop area is treated with one or more compounds selected from compounds of the general formula I and acid addition salts of such compounds in which R3 represents an amidino group.
The present invention further provides a method of dressing seeds, wherein the seeds are treated with one or more compounds selected from compounds of the general formula I and acid addition salts of such compounds in which R3 represents an amidino group.
The present invention further provides a pack which comprises one or more compounds selected from compounds of the general formula I and acid addition salts of such compounds in which R3 represents an amidino group, together with instructions for its/their use for controlling phytopathogenic fungi.
The compounds of the present invention that are distinguished by a very good fungicidal action are especially those of the general formula I in which R, represents a hydrogen atom or a methyl or ethyl group, R2 represents a phenyl, methylphenyl, dimethylphenyl, methoxyphenyl, fluorophenyl, chlorophenyl, bromophenyl, dichlorophenyl, trifluoromethylphenyl, methylthiophenyl or cyanophenyl group, R3 represents a methyl, ethyl, propyl, isopropyl, tert.-butyl, allyl, propenyl, propynyl, methoxyethyl, benzyl, chlorobenzyl, methylbenzyl, methoxybenzyl, phenyl, chlorophenyl, methylphenyl, methoxyphenyl, acetyl orchloracetyl group, and X represents an oxygen or sulphur atom or a sulphinyl or sulphonyl group.
The compounds of the present invention may be applied singly, or in the form of mixtures with one another or with other active substances. If desired, other fungicides, nematocides, insecticides or other kinds of pesticides may be added, depending on the desired aim.
The active substances are advantageously applied in the form of fungicidal preparations, for example powders, strewable preparations, granules, solutions, emulsions or suspensions, with the addition of liquid and/or solid vehicles or diluents and, if desired, of surface-active agents, for example wetting, adhesive, emulsifying and/or dispersing agents.
Suitable liquid carriers are water, mineral oils, or other organic solvents, for example xylene, chlorobenzene, cyclohexanol, dioxan, acetonitrile, ethyl acetate, dimethylformamide, isophorone and dimethyl sulphoxide.
Suitable solid carriers are, for example, lime, kaolin, chalk, talcum, attaclay and other clays as well as natural or synthetic silicic acid.
As surface-active agents there may be mentioned, for example, salts of ligninsulphonic acids, salts of alkylated benzenesulphonic acids, sulphonated acid amides and salts thereof, polyethoxylated amines and alcohols.
When the active substances are to be used for dressing seeds, dyestuffs may also be added in order to give the dressed seeds a clearly visible colour.
The proportion of active substance(s) in the fungicidal preparations may vary within wide limits, the exact concentration of the active substances used for the preparations being dependent primarily on the quantity in which the preparations are to be used. The preparations may contain, for example, between approximately 1 and 80% by weight, preferably between 20 and 50% byweight of active substance(s) and approximately 99 to 20% by weight of liquid or solid carrier and also, if desired, up to 20% by weight of surface-active agent(s).
The active substances may be applied in the usual manner, for example, by spattering, by spraying using a course spray or a spray in the form of a fine mist, by dusting, by applying in the form of a gas, or by fumigating, scattering, drenching or dressing.
The new compounds of the general formula I may be manufactured, for example, by the processes of the present invention, as defined below.
The present invention further provides a process for the manufacture of a compound of the general formula I, wherein a compound of the general formula II
in which R, and R2 have the meanings given above, is reacted in an organic solvent, if desired in the presence of an acid acceptor, with an acid halide of the general formula Ill Hal-CO-CH2-X-Fl3 (III), in which R3 and X have the meanings given above and Hal represents a halogen atom, preferably a chlorine atom. The process product may be isolated in a manner known per se.
The present invention further provides a process for the manufacture of those compounds of the general formula I in which X represents a sulphur atom, wherein a compound of the general formula V
in which R, and R2 have the meanings given above and Hal represents a halogen atom, preferably a chlorine atom, is reacted in an inert organic solvent under nitrogen with a compound of the general formula (-) B S-Fl3, in which R3 has the meaning given above and B represents an alkali metal atom, preferably a sodium atom, or, when R3 represents an amidino group, with thiourea of the formula
The compound of the general formula V has advantageously been prepared by reacting in an organic solvent, if desired in the presence of an acid acceptor, a compound of the general formula II
in which R1 and R2 have the meanings given above, with an acid halide of the general formula IV Hal'CO < H2Hal (IV), in which Hal and Hal' each represents a halogen atom, preferably a chlorine atom.
The present invention further provides a process for the manufacture of those compounds of the general formula I in which X represents a sulphinyl orsulphonyl group, wherein a compound of the general formula la
in which Fl1, R2 and R3 have the meanings given above, is reacted in a solvent with an oxidizing agent.
The compound of the general formula la may of course have been prepared by one of the other processes of the present invention, as defined above, starting from a compound of the general formula II or V.
A compound of the general formula I, in which R3 represents an amidino group, obtained by any one of the processes of the present invention, as defined above, may, if desired, be converted into an acid addition salt, for example the hydrochloride, thereof.
As acid acceptors which may optionally be used, there may be mentioned for example, organic bases, for example pyridine, triethylamine or N,N-dimethylaniline, or inorganic bases, for example hydroxides, oxides and carbonates of alkali metals and alkaline earth metals.
As solvents there may be used organic solvents, for example ether, tetrahydrofuran, benzene, toluene, xylene, ethyl acetate, acetonitrile, dimethylformamide or dimethyl sulphoxide. The reactions are advantageously carried out at temperatures of between --150C and 1 500C.
The reaction of the compounds of the general formula la to form the compounds of the general formula I, in which X represents a sulphinyl or sulphonyl group, may be carried out with oxidizing agents, for example with organic peracids, for example 3-chloroperbenzoic acid, in an inert organic solvent, for example methyl chloride or chloroform, or with inorganic reagents, for example hydrogen peroxide or potassium permanganate, at temperatures of between 0 and 1000C, in acetic acid. For preparing the sulphinyl compounds, approximately 2 oxidation equivalents are necessary and in the case of the sulphonyl compounds, approximately 4 oxidation equivalents are necessary.
The compounds of the present invention are generally almost colourless, odourless, crystalline substances or faintly yellow liquids, which are very sparingly soluble in water and benzine, but, in contrast, very readily soluble in polar solvents, for example acetone, dimethylformamide and dimethyl sulphoxide.
The starting compounds for manufacturing the compounds of the present invention are known per se or may be prepared by processes known per se.
The following Examples illustrate the invention. Examples 1 to 5 illustrate the manufacture of the compounds of the present invention and Examples 6 to 12 illustrate the possible ways of using the compounds of the present invention and their superiorfungicidal action.
EXAMPLE 1 Methoxyacetic acid [2,6-dimethyl-N-(2-oxoperhydro-3-furyl)-anilide] A mixture consisting of 9.75 g (0.47 mole) of 3-(2,6-dimethylaniline)-perhydrofuran-2-one, 6.50 g (0.06 mole) of methoxyacetyl chloride, 250 ml of toluene and 2 ml of dimethylformamide was stirred for 3 hours at 250C and then for one hour at the boiling temperature. The mixture was then concentrated to dryness in vacuo and the solid residue was digested with diisopropyl ether. After removing the crystals by suction, they were dried at 250C in vacuo.
Yield: 11.5 g = 88% of the theoretical yield.
,M.p.: 130-1310C.
EXAMPLE 2.
Acetoxyacetic acid [2 ,6-dimethyl-N-(2-oxoperhydro-3-fu ryl)-a nilide] To 10.26 g (0.05 mole) of 3-(2,6-dimethylanilino)-perhydrofuran-2-one, dissolved in 200 ml of toluene, there were added 6.85 g (0.05 mole) of acetoxyacetic acid chloride and the mixture was heated at the boil for one hour. The reaction solution was then concentrated to dryness in vacuo. The oil remaining behind was crystallized by rubbing with ether. The crystals were removed by suction and washed several times with a little ether and the resulting substance was dried at approximately 250C in vacuo.
Yield: 12.64 g = 82.8% of the theoretical yield.
M.p.: 106-1080C.
EXAMPLE 3.
Methylthio-acetic acid [2,6-dimethyl-N-(2-oxoperhydro-3-fu ryl)-anilidej 28.17 g (0.1 mole) of chloracetic acid [2,6-dimethyl-N-(2-oxoperhydro-3-furyl)-anilidej were dissolved in 120 ml of acetonitrile, and 6.5 g (0.15 mole) of sodium methylate were added thereto. The mixture was cooled to approximately -1 50C and 22.4 g (0.47 mole) of methyl mercaptan were added, while stirring. After slowly warming the mixture to 200C to 250C, it was then further stirred at this temperature for approximately twenty hours. It was then taken up in ethyl acetate/water and the alkaline aqueous phase was separated off. The organic phase was extracted once by shaking with a sodium hydroxide solution and then washed until neutrai. The ethyl acetate phase was dried over magnesium sulphate; filtered off and concentrated in vacuo.The oily residue was dried under an oil pump vacuum.
Yield: 18 g = 61.3% of the theoretical yield.
M.p.: 71--73 OC.
EXAMPLE 4 lsopropylsu Iphonyl-acetic acid [2,6-dimethyl-N-(2-oxoperhydro-3-furyl)-a nilide] 9.64 g (0.03 mole) of isopropyithio-acetic acid [2,6-dimethyl-N-(2-oxoperhydro-3-furyl)-anilidej were dissolved in 260 ml of chloroform, and 12.08 g (0.07 mole) of 3-chloroperbenzoic acid were added thereto. After stirring the mixture for four hours at room temperature, a further 6 g (0.035 mole) of 3-chloroperbenzoic acid were added. Stirring was continued for approximately 14 hours and the organic phase was extracted several times by shaking with a 1 N sodium hydroxide solution, dried over magnesium sulphate and concentrated in vacuo. The resulting crystals were digested with isoether and filtered off with suction.
Yield: 9 g = 84.9% of the theoretical yield.
M.p.: 177-1850C.
EXAMPLE 5 Dimethyldithioca rbamic acid [2,6-dimethyl-N-(2-oxoperhydro-3-fu ryl)-anilinoca rbonylmethyl] ester.
8.45 g (0.03 mole) of chloracetic acid [2,6-dimethyl-N-(2-oxoperhydro-3-furyl)-anilide] were dissolved in 100 ml of acetonitrile and, after the addition of 5.3 g (0.037 mole) of sodium dimethyl dithiocarbamate, heated at the boil for 6 hours while passing nitrogen through it. After having cooled to approximately 20-250C, the reaction mixture was poured into 400 ml of water and extracted 3 times with chloroform. The combined chloroform phases were dried over magnesium sulphate and concentrated in vacuo. The crystalline residue was filtered off with suction, washed with methanol and dried at room temperature in vacuo.
Yield: 7.7 g = 70% of the theoretical yield.
M.p.: 153-1560C.
Each of the following compounds of the present invention may be manufactured in a manner similar to that described in any of the appropriate Examples above.
Name of the compound Physical constant Methoxyacetic acid [3-chloro-N (2-oxoperhydro-3-furyl)-anilide] M.p.: Methoxyacetic acid [2,6-dimethyl-N (5-methyl-2-oxoperhydro-3-furyl)-anilide] M.p.: 113-1 140C Methoxyacetic acid [N-(2-oxoper hydro-3-furyl)-anilide] M.p.: 65--66 C Methoxyacetic acid [3-methyl-N (2-oxoperhydro-3-fu ryl)-anilide] M.p.: 115-1160C Methoxyacetic acid [2,3-dimethyl-N (2-oxoperhydro-3-furyl)-anilide] M.p.: 105-1060C Methoxyacetic acid [3-fluoro-N-( 5-methyl- 2-oxoperhydro-3-furyl)-anilide] M.p.: 75-760C Methoxyacetic acid [3-chloro-N-(5-methyl 2-oxoperhydro3-furyl)-anilide] M.p.: 81--83 C Methoxyacetic acid [2-methyl-N (2-oxope rhyd ro3-fu ryl)-a n i lide] M.p.: 66-670C Methoxyacetic acid [2-methoxy-N (2-oxoperhydro-3-fu ryl)-anilide] M.p.: 95--97 C Methoxya cetic acid [3-chloro-2-methyl-N (2-oxoperhydro-34ury1)-anilide] M.p.: 106-108 C Methoxyacetic acid [3-cyano-N (2-oxoperhydro-3-furyl)-anilide] M.p.: 93-940C Acetoxyacetic acid [3-methyl-N (2-oxoperhydro-3-furyl)-anilide] M.p.: 99-1030C Acetoxyacetic acid [N-(2-oxoper hydro-3-furyl)-anilide] M.p.: 127-1280C Acetoxyacetic acid [3-bromo-N (2-oxoperhydro-3-furyl)-anilide] M.p.: 137-1380C Acetoxyacetic acid [2,3-dimethyl-N (2-oxoperhydro-3-furyl)-anilide] M.p.: 97-980C Acetoxyacetic acid [3-fluoro-N (2-oxoperhydro-3-fu ryl)-anilide] M.p.: 96-980C Acetoxyacetic acid [3-cyano-N 2-oxoperhydro-3-furyl)-anilide] M.p.:: 140-1410C Acetoxyacetic acid [2-methyl-N (2-oxoperhyd ro-3-fu ryl)-a nilide] M.p.: 119-1200C Acetoxyacetic acid [3-chloro-N (2-oxoperhyd ro-3-furyl)-a nilide] M.p.: 123-1240C Name of the compound Physical constant Acetoxyacetic acid [3-cyano-N (2-oxoperhydro-3-furyl)-anilide] M.p.: 118-1200C Phenylthio-acetic acid [2,6-dimethyl N-(2-oxoperhydro-3-furyl)-anilide] M.p.: 103--105 C Ethylthio-acetic acid [2,6-dimethyl N-(2-oxoperhydro-3-furyl)-anilide] nD20: 1.5552 Isopropylthio-acetic acid [2 ,6-dimethyl N-(2-oxoperhydro-3-furyl)-anilide] n2g: 1.5490 tert.-Butylthio-acetic acid [2,6-dimethyl- N-(2-oxoperhydro-3-furyl)-anilide] n20: 1.5400 S-[3-Chloro-N-(2-oxoperhydro-3-fu ryl)anilinocarbonylmethyl]-thiuronium chloride M.p.: 1900C (with decomposition) Dimethyldithiocarbamic acid [3-chloro N-(2-oxoperhydro-3-furyl)-anilino- carbonylmethyl] ester M.p.: 1260C Dimethylthiocarbamic acid [3-fluoro N-(2-oxoperhydro-3-furyl)-a nilino carbonylrr,ethy!] ester M.p.: 160-1610C (3-Methylphenylthio)-acetic acid [2,6-dimethyl N-(2-oxoperhydro-3-furyl)-anilide] n2g: 1.5950 (Benzylthio)-acetic acid [2,6-dimethyl N-(2-oxoperhydro-3-furyl)-anilide] n2g 1.5720 (2-Aminophenylthio)-acetic acid [2,6dimethyl-N-(2-oxoperhydro-3-furyl)-anilide] M.p.: 150-151 0C Ch loracetoxyacetic acid [2,6-dimethyl N-(2-oxoperhydro-3-furyl)-anilide] M.p.: 11 5-11 80C Phenoxyacetic acid [2,6-dimethyl-N (2-oxoperhydro-3-furyl)-anilide] M.p.: 92-930C Chloracetoxyacetic acid [N (2-oxoperhydro-3-furyl)-anilide] M.p.: 64 C.
Chloracetoxyacetic acid [3-methyl N-(2-oxoperhydrn-34uryl)-anilide] M.p.: 82-830C Chloracetoxyacetic acid [3-bromo N-(2-oxoperhydro-3-furyl)-anilide] M.p.:124-125 C 250C Phenoxyacetic acid [3-bromo-N (2-oxoperh; dro-3-furyl)-anilide] M.p.:114 C Phenoxyacetic acid [N-(2-oxoperhydro-3-furyl)-anilide] M.p.: 120-1210C Phenoxyacetic acid [2,3-dimethyl N-(2-oxoperhydro-3-furyl)-anilide] M.p.: 80-820C Phenoxyacetic acid [3-methyl-N (2-oxoperhydro-3-furyl)-anilide] M.p.: 87-890C Name of the compound Physical constant Phenoxyacetic acid [2-methyl-N (2-oxoperhydro-3-fu ryl)-anilide] M.p.: 112-1130C Phenoxyacetic acid [3-chloro-N (2-oxoperhydro-3-furyl)-anilide] M.p.:: 93-950C Chloracetoxyacetic acid[3-chloro N-(2-oxoperhydro-3-furyl)-anilide] M.p.:102-103 OC Phenoxyacetic acid [2,6-dimethyl-N-(5 methyl-2-oxoperhydro-3-furyl)-anilide] M.p.: 142--1430C Chloracetoxyacetic acid [2,6-dimethyl-N (5-methyl-2-oxoperhydro-3-furyl)-anilide] M.p.: 94-970C S-[2,6-Dimethyl-N-(2-oxoperhydro-3-fu ryi) anilinocarbonylmethyI]-thiurnnium chloride M.p.: 26qOC (with decompositfon) Ethoxyacetic acid [2,6-dimethyl-N (2-oxoperhydro-3-furyl)-anilide] M.p.: 63CC Ethoxyacetic acid [2,6-dimethyl-N-(5 methyl-2-oxoperhydro-3-furyl)-anilide] M.p.:: 82-830C Ethoxyacetic acid [3-chloro-N (2-oxoperhydro-3-furyl)-anilide] M.p.: 100--201 C Ethoxyacetic acid [N-(2-oxoperhydro 3-furyl)-anilide] M.p.: 62-640C Ethoxyacetic acid [3-bromo-N (2-oxoperhydro-3-furyl)-anilide] M.p.: 115-1160C Ethoxyacetic acid [3-methyl-N (2-oxoperhydro-3-furyl)-anilide] M.p.: 74 76 C Ethoxyacetic acid [5-chloro-2-methyl N-(2-oxoperhydro-3-furyl)-anilide] M.p.: 101-103 0C Ethoxyacetic acid [2-chloro-N (2-oxoperhyd ro-3-furyl)-anilide] n2g: 1.5387 Methoxyacetic acid [2,6-dimethyl-N-(5butyl-2-oxoperhydro-3-furyl)-anilide] M.p.:: 80-81 "C Methoxyacetic acid [4-chloro-N (2-oxoperhydro-3-furyl)-anilide] M.p.: 105-1060C EXAMPLE 6 Limiting concentration test in the control of Pythium ultimum In a series of tests 20% strength pulverulent active substance preparations were mixed uniformly with soil that was severely infected with Pythium ultimum. The treated soil was placed in clay dishes each having a 0.5 litre capacity and, without a waiting period, 20 marrowfat pea seeds (Pisum sativum L. convar. medullareAlef.) of the "Kelvedon Wonder" variety were sown in each dish. After a cultivation period of three weeks at 20 to 240C in a greenhouse the number of healthy peas was determined and an assessment (1-4 as defined below) of the roots was carried out.
The active substances used and their application quantities, and also the results, are given in the following Table.
Root assessment: 4 = white roots without fungal necroses 3 = white roots with slight fungal necroses 2 = brown roots with fairly severe fungal necroses 1 = severe fungal necroses, mouldy roots.
Active substance Root concentration in Number of assessment Compound according to the invention mg/l of soil healthy peas (14) Methoxyacetic acid [2,6-dimethyl-N- 20 mg 1 7 4 (2-oxoperhydro-3-furyl)-anilide] 40 mg 1 5 4 80 mg 17 4 Methoxyacetic acid [3-chloro-N- 20 mg 1 7 4 (2-oxoperhydro-3-furyl)-anilide] 40 mg 1 5 4 80 mg 18 4 Methoxyacetic acid [2,6-dimethyl-N- 20 mg 1 7 4 (5-methyl-2-oxoperhydro-3-furyl)- 40 mg 1 7 4 anilide] 80 mg 16 4 Methoxyacetic acid [N-(2-oxoperhydro- 20 mg 1 7 4 3-furyl)-anilide] 40 mg 17 4 80 mg 17 4 Methoxyacetic acid [3-methyl-N- 20 mg 18 4 (2-oxoperhydro-3-furyl)-anilide] 40 mg 18 4 80 mg 19 4 Methoxyacetic acid [2,3-dimethyl-N- 20 mg 20 4 (2-oxoperhydro-3-furyl)-anilide] 40 mg 19 4 80 mg 18 4 Methoxyacetic acid [3-fluoro-N-(5-methyl- 20 mg 1 6 4 2-oxoperhydro-3-furyl)-anilide] 40 mg 1 6 4 80 mg 19 4 Methoxyacetic acid [3-chioro-N-(5-methyl- 20 mg 1 7 4 2-oxoperhydro-3-furyl)-anilide] 40 mg 18 4 80 mg 18 4 Methoxyacetic acid [2-methyl-N- 20 mg 12 3 (2-oxoperhydro-3-furyl)-anilide] 40 mg 16 4 80 mg 17 4 Methoxyacetic acid [2-methoxy-N- 20 mg 18 3 (2-oxoperhydro-3-furyl)-anilide] 40 mg 18 4 80 mg 17 4 Methoxyacetic acid [3-cyano-N- 20 mg 16 4 (2-oxoperhydro-3-furyl)-anilide] 40 mg 18 4 80 mg 18 4 Methoxyacetic acid [3-chloro-2-methyl- 20 mg 18 4 N-(2-oxoperhydro-3-furyl)-anilide] 40 mg 17 4 80 mg 19 4 Acetoxyacetic acid [2,6-dimethyl-N-(5- 20 mg 3 1 methyl-2-oxoperhydro-3-furyl)-anilide] 40 mg 12 1 80mg 18 4 Active substance Root concentration in Number of assessment Compound according to the invention mg/l of soil healthy peas (1-4) Acetoxyacetic acid [2,6-dimethyl-N- 20 mg 15 2 (2-oxoperhyd ro-3-furyl)-a nilidel 40 mg 1 6 4 8Omg 18 4 Phenylthio-acetic acid [2,6-dimethyl- 20 mg 8 1 N-(2-oxoperhydro-3-furyl)-anilide] 40 mg 10 2 80mg 19 4 Ethylthio-acetic acid [2,6-dimethyl- 20 mg 1 5 4 N-(2-oxoperhydro-3-furyl)-anilide] 40 mg 1 6 4 80 mg 18 4 Isopropylthio-acetic acid [2!6-dimethyl- 20 mg 1 6 4 N-(2-oxoperhydro-3-furyl)-anilide] 40 mg 1 6 4 80 mug 17 4 Isopropylsulphonylaceticacid 20 mg 1 6 3 [2,6-dimethyl-N-(2-oxoperhydro- 40 mg 1 7 4 3-furyl)-anilide] 80 mg 16 4 AGENT FOR COMPARISON Manganese ethylene bisdithiocarbamate 20 mg 1 1 40 mg 6 1 8Q mg 9 1 Control 1. (3 repetitions) Infected soil without treatment a) 1 1 b) O 1 c) O 1 Control ll. (3 repetitions) Steamed soil a) 17 4 b) 18 4 c) 18 4 EXAMPLE 7 Control of Phytophthora nicotianae var. nicotianae in the pot cultivation of Sinningia speciosa In a series of tests young Sinningia plants of the "Berliner Rot" variety were potted in clay pots each having a diameter of 11 cm. The potting substrate was a mixture of 1 part peat culture substrate and 1 part compost soil. After plotting, 100 ml of the preparation under test and having the concentration listed in the Table below were poured once over the plants. Three days later, the pots were uniformly inoculated with mycelium flocci of a three-week-old Phytophthora culture. There then followed a cultivation period of 7 weeks at 22 to 240C in a greenhouse.
The active substances used and their application quantities, and also the results, are given in the following Table.
Plant loss Average fresh Active substance after weight of plants Compound according to the invention concentration 7 weeks after 7 weeks Methoxyacetic acid [2,6-dimethyl- 0.01% 0% 180 g N-(2-oxoperhydro-3-furyl)-anilide] 0.02% 0% 1 92 g Methoxyacetic acid [N- 0.01% 0% 176 g (2-oxoperhydro-3-furyl)-anilide] 0.02% 0% 200 g Control 1.
inoculated - 80% 145g Control 11.
not inoculated 0% 184g EXAMPLE 8 Control of Phytophthora parasitica var. nicotianae in tobacco cultivation In a series of tests young tobacco plants of the "Havana" variety were potted in clay pots each having a diameter of 1 4 cm. The potting substrate was a mixture of 1 part peat culture substrate and one part sandy compost soil. After potting, 100 ml of the preparation under test and having the concentration listed in the Table below were poured once over the plants. Three days later, the pots were uniformly inoculated with mycelium flocci of a four-week-old Phytophthora culture. There then followed a cultivation period of 4 weeks at 24 to 260C in a greenhouse.
The active substances used and their application quantities, and also the results, are given in the following Table.
Plant loss Average fresh Active substance after weight of plants Compound according to the invention concentration 4 weeks after 4 weeks Methoxyacetic acid [2,6-dimethyl-N-(5- 0.01% 0% 2159 methyl-2-oxoperhydro-3-furyl)-anilide] 0.02% 0% 230 g Methoxyacetic acid [2,6-dimethyl-N- 0.01% 0% 225 g (2-oxoperhydro-3-furyl)-anilide] 0.02% 0% 227 g Control.
inoculated - 100% Og Control II.
not inoculated 0% 260 g EXAMPLE 9 Control of Phytophthora capsici in the cultivation of paprika (Capsicum annuum) In a series of tests young paprika plants were potted in clay pots each having a diameter of 14 cm.
The substrate was a mixture of 1 part peat culture substrate and one part sandy compost soil. Three days after potting, 100 ml of the preparation under test and having the concentration listed in the Table below were poured once over the plants. Three days later, the pots were uniformly inoculated with mycelium flocci of a four-week old Phytophthora culture. There then followed a cultivation period of 4 weeks at 24 to 260C in a greenhouse.
The active substances and their application quantities, and also the results, are given in the following Table.
Active Plant loss substance after Compound according to the invention concentration 4 weeks Methoxyacetic acid [2,6-dimethyl-N- 0.01% 20% (2-oxoperhydro-3 4uryI)-anilide] 0.02% 0% 0.04% 0% Methoxyacetic acid [3-chloro-N- 0.01% 40% (2-oxoperhydro-3-furyl)-anilide] 0.02% 0% 0.04% 0% Control I.
inoculated - 100% Control II.
not inoculated 0% EXAMPLE 10 Control of Phytophthora cryptogaea in the pot cultivation of Senecio cruentus In a series of tests young Cineraria plants of the "Erfurter Zwerg" variety were potted in clay pots each having a diameter of 11 cm. The potting substrate was a mixture of 1 part peat culture substrate and 1 part sandy compost soil. Three days after potting, 100 ml of the preparation under test and having the concentration listed in the Table below were poured once over the plants. Three days later, the pots were uniformly inoculated with mycelium flocci of a three-week-old Phytophthora culture.
There then followed a cultivation period of 7 weeks at 20 to 220C in a greenhouse.
The active substances used and their application quantities, and also the results. are given in the following Table.
Active Plant loss substance after Compound according to the invention concentration 7 weeks Methoxyacetic acid [2 ,6-dimethyl-N- 0.01% 0% (2-oxoperhydro-3-furyl)-anilide] 0.02o/o 0% Methoxyacetic acid [2 ,6-dimethyl -N -(5- 0.01% 20% methyl-2-oxoperhydro-3-furyl)-anilide] 0,02% 0% Control.
inoculated 100% Control 11 not inoculated ~ 0% oyO EXAMPLE 11 Dressing of French bean seeds In a series of tests French bean seeds (Phaseolus vulgaris var. nan us) of the "Wachs Beste von Ailen" variety were dressed with 20% strength pulverulent active substance preparations. Clay dishes each of 2 litres capacity (20 x 20 x 5 cm) were filled with normal compost soil (damping-off) and 25 of the bean seeds were sown in each dish. After a cultivation period of 15 days at 19 to 21 0C in a greenhouse, the number of healthy seedlings was determined.
The active substances used and their application quantities, and also the results, are given in the following Table.
Active substance Yo pf healthy plants Fresh weight Compound according to the invention in g/kg of seeds from the seeds per plant Methoxyacetic acid [2,6-dimethyl-N- 0.12 100% 3.8 9 (2-oxoperhydro-3-furyl)-anilide] 0.25 96% 3.9 g 0.50 100% 3.Bg Methoxyacetic acid [3'-chlorn-N- 0.12 100% 4.2 g (2-oxoperhydro-3-furyl)-anilide] 0.25 100% 4.3 g 0.50 100% 3.7 9 Methoxyacetic acid [2,6-dimethyl-N-(5- 0.12 100% 3.8 g methyl-2-oxoperhydro-3-furyl)-anilide] 0.25 100% 4.2 g 0.50 96% 4.1 g Active substance % of healthy plants Fresh weight Compound according to the invention in g/kg of seeds from the seeds per plant Methoxyacetic acid [N- 0.12 100% 4.0 g (2-oxoperhydro-3-furyl)-anilide] 0.25 100% 4.2 g 0.50 100% 3.9 9 Methoxyacetic acid [3-methyl-N- 0.12 100% 3.6 g (2-oxoperhydro-3-furyl)-anilide] 0.25 100% 4.1 g 0.50 100% 4.2 g AGENTS FOR COMPARISON Tetramethylthiuram 0.25 16% 3.2 g disulphide 0.50 68% 3.8 g 1.00 72% 3.3 g Control 1.
Infected soil a) 0% b) 0% c) 0% Control 11.
Steamed soil a) 96% 4.2 g b) 100% 4.1 9 c) 100% 4.1 g EXAMPLE 12 The effect of a prophylactic treatment of the foliage against Plasmopara viticola in vines in a greenhouse In a series of tests young vines having approximately 5 to 8 leaves were sprayed until dripping wet with an active substance concentration of 0.025% and, after the spray coating had dried, were sprayed on the undersides of the leaves with an aqueous suspension of sporangia of the fungus indicated in the heading above (approximately 20,000 per ml) and then immediately incubated in a greenhouse at 22 to 240C in an atmosphere as saturated with water vapour as possible.
From the second day onwards, the air humidity was reduced to the normal level (30 to 70% saturation) for three to four days and then maintained at water vapour saturation for a further day. The percentage proportion of the surface attacked by fungi of each leaf was then recorded and the average per treatment was calculated as follows to determine the fungicidal effect: 1 00 100. attack in treated plants = % effect attack in untreated plants The active substances used and the results are given in the following Table.
Compound according to the invention % Effect Methoxyacetic acid [2,6-dimethyl-N (2-oxoperhydro-3-furyl)-anilide] 100 Methoxyacetic acid [3-chloro-N (2-oxoperhydro-3-furyl)-anilide] 100 Methoxyacetic acid [2,6-dimethyl-N-(5methyl-2-oxoperhydro-3-furyl)-anilide] 100 Methoxyacetic acid [N-(2-oxoperhydro3-furyl)-anilide] 100 Methoxyacetic acid [3-methyl-N (2-oxoperhydro-3-furyl)-anilide] 100 Compound according to the invention % Effect Methoxyacetic acid [2,3-dimethyl-N (2-oxoperhydro-3-furyl)-anilide] 100 Methoxyacetic acid [3-fluoro-N-(5-methyl 2-oxoperhydro-3-furyl)-anilide] 100 Methoxyacetic acid [3-chloro-N-(5-methyl 2-oxoperhydro-3-furyl)-anilide] 100 Acetoxyacetic acid [2,6-dimethyl-N-(5- methyl-2-oxoperhydro-3-furyl)-anilide] 74 Phenylthio-acetic acid[2,6-dimethyl-N (2-oxoperhydro-3-furyl)-anilide] 98 Acetoxyacetic acid [2-methyl-N (2-oxoperhydro-3-furyl )-anilide] 74 Acetoxyacetic acid [2,6-dimethyl-N (2-oxoperhydro-3-furyl)-anilide] 100 Methoxyacetic acid [2-methyl-N (2-oxoperhydro-3-furyl)-anilide] 100 Methoxyacetic acid [2-methoxy-N-(oxoperhydro-3-furyl)-anilide] 100 Methoxyacetic acid [3-chloro-2-methyl-N (2-oxoperhydro-3-furyl)-anilide] 100 Acetoxyacetic acid [3-chloro-N (2-oxoperhydro-3-furyl)-anilide] 98 Acetoxyacetic acid [3-cyano-N (2-oxoperhydro-34ury1)-anilide] 74 Methoxyacetic acid [3-cyano-N (2-oxoperhydro-3-furyl)-anilide] 100 Ethylthio-acetic acid[2,6-di methyl-N (2-oxoperhydro-3-furyl)-anilide] 100 Isopropylthio-acetic acid[2,6-dimethyl-N (2-oxoperhydro-3-furyl)-anilide] 100 tert.-Butylthio-acetic acid[2,6-dimethyl N-(2-oxoperhydro-3-furyl)-anilide] 95 Isopropylsulphonylacetic acid [2,6-dimethyl N-(2-oxoperhydro-3-furyl)-anilide] 100

Claims (117)

1. An acetic acid anilide of the general formula I
in which R, represents a hydrogen atom or a C1-C4-alkyl group, R2 represents an unsubstituted aromatic hydrocarbon group or an aromatic hydrocarbon group substituted by one or more substituents selected from C1-C4-alkyl groups, C1-C4-alkoxy groups, C,C4-alkylthio groups, halogen atoms, trifluoromethyl groups, nitro groups, C,-C,-alkoxycarbonyl groups and cyano groups, R3 represents a C1-C6-alkyl, halogeno-C,-C,-alkyl, C1-C4-alkoxy-C1-C4-alkyl, C2-C5-alkenyl, C3-C6-alkynyl, C1-C6-alkylcarbonyl or halogeno-C1-C6-alkylcarbonyl group, or represents an unsubstituted phenyl or benzyl group or a phenyl or benzyl group substituted by one or more substituents selected from halogen atoms and C1-C4-alkyl, C1-C4-alkoxy, C,C4-alkylthio, trifluoromethyl, nitro and amino groups, or represents an amidino or dimethylthio-carbamoyl group, and X represents an oxygen sulphur atom or a sulphinyl or sulphonyl group.
2. An acid addition salt of a compound as claimed in claim 1 in which R3 represents and amidino group.
3. A compound as claimed in claim 1, wherein R, represents a hydrogen atom or a methyl or ethyl group, R2 represents a phenyi, methylphenyl, dimethylphenyl, methoxyphenyl, fluorophenyl, chlorophenyl, bromophenyl, dichlorophenyl, trifluoromethylphenyl, methylthiophenyl or cyanophenyl group, R3 represents a methyl, ethyl, propyl, isopropyl, tert.-butyl, allyl, propenyl, propynyl, methoxyethyl, benzyl, chlorobenzyl, methylbenzyl, methoxybenzyl, phenyl, chlorophenyl, methylphenyl, methoxyphenyl, acetyl or chloracetyl group, and X represents an oxygen or sulphur atom or a sulphinyl or sulphonyi group.
4. Methoxyacetic acid [2 ,6-dimethyl-N-(2-oxoperhydro-3-furyl)-anilide].
5. Acetoxyacetic acid [2,6-dimethyl-N-(2-oxope rhydro-3-furyl)-anilide].
6. Methyithio-acetic acid [2,6-dimethyl-N-(2-oxoperhydro-3-furyl)-anilide].
7. Dimethyldithiocarbamic acid [2,6-dimethyl-N-(2-oxoperhydro-3-furyl)-anilinocarbonylmethyl] ester
8. Methoxyacetic acid {3-chloro-N-(2-oxoperhydro-3-furyl)-anilide].
9. Methoxyacetic acid [2,6-dimethyl-N-( 5-methyi-2-oxoperhydro-3-furyl)-anilide]
10. Methoxyacetic acid [N-(2-oxoperhydro-3-furyl)-anilide].
11. Methoxyacetic acid [3-methyl-N-(2-oxoperhydro-3-furyl)-anilide].
12. Methoxyacetic acid [2,3-dimethyl-N-(2-oxoperhydro-3-furyl)-anilidej.
13. Methoxyacetic acid [3-fluoro-N-(5-methyl-2-oxoperhydro-3-furyl)-anilide].
14. Methoxyacetic acid [3-chloro-N-(5-methyl-2-oxoperhydro-3-furyl)-anilide].
1 5. Methoxyacetic acid [2-methyl-N-(2-oxoperhydro-3-furyl)-anilide].
1 6. Methoxyacetic acid [2-methoxy-N-(2-oxoperhydro-3-furyl)-a nilide].
17. Methoxyacetic acid [3-chloro-2-methyl-N-(2-oxoperhydro-34uryI)-anilide].
18. methoxyacetic acid [3-cyano-N-(2-oxoperhydro-3-furyl)-a nilide].
19. Acetoxyacetic acid [3-methyl-N-(2-oxoperhyd ro3-fu ryl)-a ni lide].
20. Acetoxyacetic acid [N-(2-oxoperhydro-3-furyl)-anilide].
21. Acetoxyacetic acid [3-bromo-N-(2-oxoperhydro-3-furyl)-anilide].
22. Acetoxyacetic acid [2,3-dimethyl-N-(2-oxoperhydro-3-furyl)-anilide].
23. Acetoxyacetic acid [3-fl uoro-N-(2-oxoperhydro-3-furyl)-anilide].
24. Acetoxyacetic acid [2,6-dimethyl-N-(5-methyl-2-oxoperhydro-3-furyl)-anilide].
25. Acetoxyacetic acid [2-methyl-N-(2-oxoperhyd ro-3-furyl)-a nilide].
26. Acetoxyacetic acid [3-chloro-N-(2-oxoperhydro-3-furyl)-anilide].
27 Acetoxyacetic acid [3-cyano-N-(2-oxoperhydro-3-furyl)-anilide].
28. Phenylthio-acetic acid[2,6-dimethyl-N-(2-oxoperhydro-3-furyl)-anilide].
29. Ethylthio-acetic a cid[2,6-di methyl-N-(2-oxoperhydro-3-furyl)-a nilide].
30. Isopropylthio-acetic acid[2,6-dimethyl-N-(2-oxoperhydro-3-furyl)-anilide].
31. tert.-Butylthio-acetic acid [2,6-dimethyl-N-(2-oxoperhydro-3-furyl)-anilide].
32. S-[3-Chloro-N-(2-oxoperhydro-3-furyl)-anilinocarbonylmethyl]-thiuronium chloride.
33. Dimethyldithiocarbamic acid [3-chloro-N-(2-oxoperhydro-3-furyl)-anilinocarbonylmethylj ester.
34. Dimethylthiocarbamic acid [3-fluoro-N-(2-oxoperhydro-3-furyl)-anilinocarbonylmethyl] ester.
35. (3-Methylphenylthio)-acetic acid [2,6-dimethyl-N-(2-oxoperhydro-3-furyl)-anilide].
36. (Benzylthio)-acetic acid [2,6-dimethyl-N-(2-oxoperhydro-3-furyl)-a nilide].
37. (2-Aminophenylthio)-acetic acid [2,6-di methyl-N-(2-oxoperhyd ro-3-furyl)-anilide] .
38. Ch loracetoxyacetic acid [2,6-dimethyl-N-(2-oxoperhydro-3-furyl)-a nilide].
39. Phenoxyacetic acid [2,6-dimethyl-N-(2-oxoperhydro-3-furyl)-anilide].
40. Chloracetoxyacetic acid [N-(2-oxoperhydro-3-furyl)-anilide].
41. Chloracetoxyacetic acid [3-methyl-N-(2-oxoperhydro-3-furyl)-anilide].
42. Chloracetoxyacetic acid [3-bromo-N-(2-oxoperhydro-3-furyl)-anilide].
43. Phenoxyacetic acid [3-bromo-N-(2-oxoperhydro-3-furyl)-anilide].
44. Phenoxyacetic acid [N-(2-oxoperhydro-3-furyl)-anilide].
45. Phenoxyacetic acid [2,3-dimethyl-N-(2-oxoperhydro-3-fu ryl)-a nilide].
46. Phenoxyacetic acid [3-methyl-N-(2-oxoperhydro-3-furyl)-anilide].
47. Phenoxyacetic acid [2-methyl-N-(2-oxoperhydro-3-furyl)-anilide].
48. Phenoxyacetic acid [3-ch loro-N-(2-oxoperhydro-3-fu ryl)-a nilide] .
49. Chloracetoxyacetic acid [3-chloro-N-(2-oxoperhydro-3-furyl)-a nilide].
50. Phenoxyacetic acid [2,6-dimethyl-N-(5-methyl-2-oxoperhydro-3-furyl)-anilide].
51. Ch loracetoxyacetic acid [2,6-di methyl-N-( 5-methyl-2-oxoperhydro-3-furyl)-an ilide].
52. S-[2,6-Di methyl-N-(2-oxoperhydro-3-furyl)-a nilinoca rbonylmethyl]-thiuron ium chloride.
53. Isopropylsulphonyl-acetic acid [2,6-dimethyl-N-(2-oxoperhydro-3-furyl)-anilide].
54. Ethoxyacetic acid [2,6-di methyl-N-(2-oxoperhydro-3-furyl)-a nilide].
55. Ethoxya cetic acid [2,6-dimethyl-N-(5-methyl-2-oxoperhydro-3-furyl)-anilide].
56. Ethoxyacetic acid [3-chloro-N-(2-oxoperhydro-3-fu ryl)-anilide] .
57. Ethoxyacetic acid [N-(2-oxoperhydro-3-furyl)-anilide].
58. Ethoxyacetic acid [3-bromo-N-(2-oxoperhydro-3-fu ryl)-anilide] .
59. Ethoxyacetic acid [3-methyl-N-(2-oxoperhydro-3-furyl)-anilide].
60. Ethoxyacetic acid [5-ch loro-2-methyl-N-( 2-oxoperhydro-3-furyl)-a nilide].
61. Ethoxyacetic acid [2-chloro-N-(2-oxoperhydro-3-furyl)-anilide].
62. Me thoxyacetic acid [2,6-dimethyl-N-( 5-butyl-2-oxoperhydro-3-furyl)-anilide].
63. Methoxyacetic acid [4-chloro-N-(2-oxoperhydro-3-furyl)-anilide].
64. A process for the manufacture of a compound of the general formula I given in claim 1, in which R1, R2, R3 and X have the meanings given in claim 1, wherein a compound of the general formula II
in which Rt and R2 have the meanings given in claim 1, is reacted in an organic solvent with an acid halide of the general formula III HaIO-CH2-X-Fl2 (III) in which R3 and X have the meanings given in claim 1 and Hal represents a halogen atom.
65. A process as claimed in claim 64, wherein Hal represents a chlorine atom.
66. A process as claimed in claim 64 or 65, wherein the reaction is carried out in the presence of an acid acceptor.
67. A process as claimed in any one of claims 64 to 66, wherein a resulting compound of the general formula I, in which X represents a sulphur atom, is reacted in a solvent with an oxidizing agent to form a corresponding compound of the general formula I in which X represents a sulphinyl or sulphonyl group.
68. A process as claimed in any one of claims 64 to 67, wherein a resulting compound of the general formula I, in which R3 represents an amidino group, is converted into an acid addition salt thereof.
69. A process as claimed in claim 64, conducted substantially as described herein.
70. A process for the manufacture of a compound of the general formula I given in claim 1, in which Rr, R2 and R3 have the meanings given claim 1 and X represents a sulphur atom, wherein a compound of the general formula V
in which R1 and R2 have the meanings given in claim 1 and Hal represents a halogen atom, is reacted in an inert organic solvent under nitrogen with a compound of the general formula (-) B S-Fl3, in which R3 has the meaning given in claim 1 and B represents an alkali metal atom, or, when R3 represents an amidino group, with thiourea of the formula
71 A process as claimed in claim 70, wherein Hal represents a chlorine atom.
72. A process as claimed in claim 70 or 71, wherein B represents a sodium atom.
73. A process as claimed in any one of claims 70 to 72, wherein the resulting compound of the general formula I is reacted in a solvent with an oxidizing agent to form a corresponding compound of the general formula I in which X represents a sulphinyl or sulphonyl group.
74. A process as claimed in any one of claims 70 to 73, wherein a resulting compound of the general formula I, in which R3 represents an amidino group, is converted into an acid addition salt thereof.
75. A process as claimed in any one of claims 70 to 74, wherein the compound of the general formula V has been prepared by reacting in an organic solvent a compound of the general formula II
in which Rt and R2 have the meanings given in claim 1, with an acid halide of the general formula IV Hal'-COH2-Hal (IV), in which Hal and Hal' each represents a halogen atom.
76. A process as claimed in claim 75, wherein Hal and Hal' each represents a chlorine atom.
77. A process as claimed in claim 75 or 76, wherein the reaction with the compound of the general formula IV is carried out in the presence of an acid acceptor.
78. A process as claimed in claim 70, conducted substantially as described herein.
79. A process for the manufacture of a compound of the general formula I given in claim 1, in which R1, R2 and R3 have the meanings given in claim 1 and X represents a sulphinyl or sulphonyl group, wherein a compound of the general formula la
in which Fl1, R2 and R3 have the meanings given in claim 1, is reacted in a solvent with an oxidizing agent.
80. A process as claimed in claim 79, wherein a resulting compound of the general formula I, in which R3 represents an amidino group, is converted into an acid addition salt thereof.
81. A process as claimed in claim 79, conducted substantially as described herein.
82. A process for the manufacture of a compound as claimed in claim 1, conducted substantially as described in any one of Examples 1 to 5 herein.
83. A fungicidal preparation which comprises a compound of the general formula I given in claim 1, in which Fl1, R2, R3 and X have the meanings given in claim 1, in admixture of conjunction with a suitable carrier.
84. A fungicidal preparation which comprises a salt as claimed in claim 2, in admixture or conjunction with a suitable carrier.
85. A fungicidal preparation which comprises a compound as claimed in claim 3, in admixture or conjunction with a suitable carrier.
86. A fungicidal preparation which comprises the compound claimed in any one of claims 4 to 63, in admixture or conjunction with a suitable carrier.
87. A preparation as claimed in any one of claims 83 to 86, which is in the form of a powder, a strewable preparation, granules, a solution, an emuision or a suspension.
88. A preparation as claimed in any one of claims 83 to 87, containing a single compound selected from compounds of the general formula I and acid addition salts of such compounds in which R3 represents an amidino group.
89. A preparation as claimed in any one of claims 83 to 87, containing two or more compounds selected from compounds of the general formula I and acid addition salts of such compounds in which R3 represents an amidino group.
90 A preparation as claimed in any one of claims 83 to 89, which also contains one or more active substances selected from fungicides and pesticides other than compounds as claimed in claims 1 and 2.
91. A preparation as claimed in any one of claims 83 to 90, wherein the total amount present of active substance or substances is approximately 1 to 80% by weight.
92. A preparation as claimed in claim 91, wherein the total amount present of active substance or substances is 20 to 50% by weight.
93. A preparation as claimed in any one of claims 83 to 92, containing a single surface-active agent in an amount of up to 20% by weight.
94. A preparation as claimed in any one of claims 83 to 92, containing two or more surface-active agents in a total amount of up to 20% by weight.
95. A preparation as claimed in any one of claims 83 to 94, which also contains a dyestuff.
96. Any one of the fungicidal preparations as claimed in claim 83 and substantially as described in Examples 6 to 12 herein.
97. A method of protecting a living plant against phytopathogenic fungi, wherein the living plant and/or the area in the vicinity of the living plant is/are treated with a compound of the general formula I given in claim 1, in which Fl1, R2, R3 and X have the meanings given in claim 1.
98. A method of protecting a living plant against phytopathogenic fungi, wherein the living plant and/or the area in the vicinity of the living plant is/are treated with a salt as claimed in claim 2.
99. A method as claimed in claim 97, wherein the treatment is carried out with a compound as claimed in claim 3.
100. A method as claimed in claim 97 or 98, wherein the treatment is carried out with the compound claimed in any one of claims 4 to 63.
101. A method as claimed in claim 97 or 98, wherein the treatment is carried out with a fungicidal preparation as claimed in any one of claims 83 to 94 and 96.
102. A method as claimed in claim 97, conducted substantially as described in any one of Examples 7 to 10 and 12 herein.
1 03. A method of protecting a crop area against phytopathogenic fungi, wherein the crop area is treated with a compound of the general formula I given in claim 1, in which Fl1, R2, R3 and X have the meanings given in claim 1.
1 04. A method of protecting a crop area against phytopathogenic fungi, wherein the crop area is treated with a salt as claimed in claim 2.
1 05. A method as claimed in claim 103, wherein the crop area is treated with a compound as claimed in claim 3.
106. A method as claimed in claim 103 or 104, wherein the crop area is treated with the compound claimed in any one of claims4 to 63.
1 07. A method as claimed in claim 103 or 104, wherein the crop area is treated with a fungicidal preparation as claimed in any one of claims 83 to 94 and 96.
108. A method as claimed in claim 103, conducted substantially as described in Example 6 herein.
109. A method of dressing seeds, wherein the seeds are treated with a compound of the general formula I given in claim 1, in which R1, R2, R3 and X have the meanings given in claim 1.
110. A method of dressing seeds, wherein the seeds are treated with a salt as claimed in claim 2.
111. A method as claimed in claim 109, wherein the seeds are treated with a compound as claimed in claim 3.
112. A method as claimed in claim 109 or 110, wherein the seeds are treated with the compound claimed in any one of claims 4 to 63.
113. A method as claimed in claim 109 or 110, wherein the seeds are treated with a fungicidal preparation as claimed in any one of claims 83 to 96.
11 4. A method as claimed in claim 109, conducted substantially as described in Example 11 herein.
115. A pack which comprises a compound of the general formula I given in claim 1, in which Rs, R2, R3 and X have the meanings given in claim 1, together with instructions for its use for controlling phytopathogenic fungi.
11 6. A pack which comprises a salt as claimed in claim 2, together with instructions for its use for controlling phytopathogenic fungi.
117. A pack as claimed in claim 11 5, wherein the compound of the general formula I is a compound as claimed in claim 3.
11 8. A pack which comprises the compound claimed in any one of claims 4 to 163, together with instructions for its use for controlling phytopathogenic fungi.
GB7932156A 1978-09-22 1979-09-17 Fungicidally active acetic acid anilides and their manufacture and use Expired GB2033379B (en)

Applications Claiming Priority (1)

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DE19782841824 DE2841824A1 (en) 1978-09-22 1978-09-22 ACETIC ACID ANILIDE, METHOD FOR PRODUCING THESE COMPOUNDS, AND THIS FUNGICIDAL CONTAINER

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AT (1) AT365890B (en)
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BE (1) BE878924A (en)
BG (1) BG30624A3 (en)
BR (1) BR7905455A (en)
CS (1) CS219905B2 (en)
DD (1) DD145989A5 (en)
DE (1) DE2841824A1 (en)
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ES (1) ES483787A1 (en)
FR (1) FR2436782A1 (en)
GB (1) GB2033379B (en)
HU (1) HU182612B (en)
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IT (1) IT1165288B (en)
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DE2845454A1 (en) * 1977-11-01 1979-05-10 Chevron Res 3- (N-ACYL-N-ARYLAMINO) - GAMMA -BUTYROLACTONE AND - GAMMA -BUTYROTHIOLACTONE AND FUNGICIDE AGENTS
JPH02124375U (en) * 1989-03-27 1990-10-12

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PL119374B1 (en) 1981-12-31
ZA795021B (en) 1980-09-24
BE878924A (en) 1980-03-21
PL218428A1 (en) 1980-07-14
RO78587A (en) 1982-03-24
IT1165288B (en) 1987-04-22
GB2033379B (en) 1982-12-22
LU81703A1 (en) 1980-01-24
CS219905B2 (en) 1983-03-25
YU204879A (en) 1983-02-28
FR2436782A1 (en) 1980-04-18
FR2436782B1 (en) 1983-07-22
ES483787A1 (en) 1980-05-16
ATA622679A (en) 1981-07-15
DK346179A (en) 1980-03-23
DD145989A5 (en) 1981-01-21
IT7925202A0 (en) 1979-08-21
JPS5545682A (en) 1980-03-31
HU182612B (en) 1984-02-28
SU988191A3 (en) 1983-01-07
IL58273A0 (en) 1979-12-30
AU5107679A (en) 1980-04-17
BG30624A3 (en) 1981-07-15
DE2841824A1 (en) 1980-04-03
BR7905455A (en) 1980-05-20
AT365890B (en) 1982-02-25

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