CA1194488A - N-(alk-1-enyl)-carboxylic acid anilides, processes for their preparation and their use as fungicides - Google Patents

N-(alk-1-enyl)-carboxylic acid anilides, processes for their preparation and their use as fungicides

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CA1194488A
CA1194488A CA000411676A CA411676A CA1194488A CA 1194488 A CA1194488 A CA 1194488A CA 000411676 A CA000411676 A CA 000411676A CA 411676 A CA411676 A CA 411676A CA 1194488 A CA1194488 A CA 1194488A
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radical
compound
formula
hydrogen atom
general formula
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Rudolf Thomas
Wilhelm Brandes
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Bayer AG
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Bayer AG
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/04—Sulfonic acids; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/10—Sulfones; Sulfoxides
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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    • 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
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N49/00—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds containing the group, wherein m+n>=1, both X together may also mean —Y— or a direct carbon-to-carbon bond, and the carbon atoms marked with an asterisk are not part of any ring system other than that which may be formed by the atoms X, the carbon atoms in square brackets being part of any acyclic or cyclic structure, or the group, wherein A means a carbon atom or Y, n>=0, and not more than one of these carbon atoms being a member of the same ring system, e.g. juvenile insect hormones or mimics thereof
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C233/07—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/65—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
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    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
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    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
    • C07D233/88—Nitrogen atoms, e.g. allantoin
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    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
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    • C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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
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    • 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
    • C07D307/28—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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  • General Health & Medical Sciences (AREA)
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  • Insects & Arthropods (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Pyrane Compounds (AREA)
  • Furan Compounds (AREA)

Abstract

Abstract N-(alk-1-enyl)-carboxylic acid anilides, processes for their preparation and their use as fungicides The compounds of the general formula (I) (I) are novel and are obtained by various processes, for example, when azines are reacted with acid derivatives.
The compounds of formula (I) are active compounds which are suitable for use as plant protection, agents, in particular, as fungicides, and can be employed with particularly good success for combating Oomycetes, for example against the blight and late blight of tomato and potato causative organism. (Phytophora infestans).

Description

The present invention relates to certain new N-(alk-l-enyl)-carboxylic acid anilides, to several processes for their production and to their use as fungicidesD
It has already been disclosed that zinc ethylene-1,2-bis-dithiocarbamate possesses good fungicidal properties (see R. Wegler Chemie der Pflanzenschutz- und Schadlingsbekàmpfungsmittel (Chem-- istry of Plant Protection Agents and Pest-combating Agents), volume
2; page 65, 1970). It is also kno~n -that alkyl N-chloroacetyl-N-(2,6-dialkylphenyl)-alanines, such as ethyl N-chloroacetyl-N-(2,6-dimethylphenyl)-alanine, can be employed with good success for combating fungal plant diseases (see DE-OS (German Published Specification) 2,350,9~4). However, the action of the compounds mentioned is not always completely sa-tisfactory, particularly when low amounts and concentrations are used, and particularly, also when combating Phytophthora species.
The present invention now provides, as new compounds, the N-(alk-1-enyl)-carboxylic acid anilides of the general formula x2 ~ N R (I) in which R1 represents a hydrogen a-tom or an alkyl radical, R2 represents a hydrogen atom, R3 represents a hydrogen atom or an al]syl or alkenyl radical or Xl, x2 and X3 independently of one ano-ther represen-t a hydrogen or fluorine chlorine or bromine atom or a straight chain or branched alkyl radical having l to ~ carbon a-toms, Y represen-ts a grouping of the general formula ~;

Az, -CH2Az, -C~2OR
wherein R8 represents an alkyl, alkenyl or alkinyl radical, and Az represents a pyrazol-l-yl, 1,2,4-triazol-]-yl or imidazol-l-yl radical, and when Y represents ~z or -CH2-Az, the physiologically tolerated acid addition salts and metal salt complexes thereof comprising salts of metals of main groups II to IV and of sub groups I and II and IV to VIII of the periodic table.
According to the present invention we further provide a pr~cess for the production of a compound of the present invention, characterized in that (a) an azine of the general formula X Y-- ~ R (II) ~ 5 in which R1, X1, x2 and X3 have the meanings given above, and R represents a hydrogen a-tom or an alkyl, alkoxy, alkoxyalkyl, hy-droxyalkyl or benzyl radical., and R5 represents a hydrogen a-tom or an alkyl, alkenyl, alkoxy, alkoxyalkyl, alkylcarbonyl, alkylcarbonyl-alkyl, alkoxycarbonyl or alkoxycarbonylalkyl radical., or R4 and R5 together represent the radical of the general formula =C
\ R7 wherein R6 represents a hydrogen atom or an alkyl radical and R represents an al~syl or phenyl radical, is reacted with an acid derivative of the general formula Hal - CO - Y (III) in which Hal represents a chlorine ox bromine atom, and Y has the meaning yiven above, if appropriate in the presence of a diluent, and the resulting acetanilide of the general formula 1 R Hal X ~ - ~ CH / (IV) in which Rl, R4, R5, Xl, X2, X3 and Y have the meaning given above, Hal is subjected, without being isolated beforehand, to a process for the elimination of hydrogen halide, if appropria-te in the presence of a base, or (b)' a carbamic acid-chloride of the general formulaRl R2 \C = C/
~2 ~ -- N \ R3 (V) Co - Cl in which Rl, R2, R3, Xl, x2 and X3 have the meanings given above, is reacted with a compound of the general formula s - Y' (VI) in which Y' represents Az wherein Az has the meanings given above and B represents a hydrogen atom or an alkali metal, if appropria-te in the presence of a diluent and if appropria-te in the presence of an acid~binding agent, or (c) a chloroacetamide of -the general formula Rl ~R2 X ~ N ? \ R3 (VII) X3 / CO - CH2 - Cl in which R1, R2, R3, Xl, x2 and X3 have the meanings given above, is reacted with a compound of the general formula ~ ~ Y (VIII) in which yll represents A~ or a grouping of -the general formula _oR8 wherein Az and R8 have the meanings given above, if appropriate i.n t~e presence of a diluent and if appropriate in the presence of an acid-bindi~g agent~ or (d) a hydroxyace-tanilide of the general formula Rl R2 X ~ ,, C = C (IX) in which Rl, R2, R3, Xl, x2 and X3 have the meanings given above, if appropriate after activation by means of an alkali me-tal, is reacted with a halide of the genexal formula Hal - Y ''' (X) in which ~ ''' represents R wherein R has the meanings given above, and Hal represents a chlorine or bromine atom, in the presence oi a diluent and if appropria-te in the presence of an acid-binding agent and, when Y in the product of reaction variant (a), (b), or (c) represents Az or -CH2-Az, an acid or a metal salt is added, if desired, onto -the said product.

- ~ -Cf the reaction variants given, which particular one is used in the individual case depends in pzrticular cn the availability of the partlcular starting r.aterials requiredO
The new N-(alh-l-enyl)-carboxylic acid anilides of the present invention possess po~erful fungicidal Froper-ties. In this respect, the compounds according to the present invention surprisingly exhibit a greater acticn than the compounds zinc et~.y ene-1,2-bis-dithiocarbamate and N-chloroacetyl~i-(2~6-dimeth~lphenyl)-alanine esters, which are known from the state o~ the art. The substances zccor-ding to the inventior. thus represent an enrichment of the art.
Preferred N-(alJk-l-en~-l)-carboxylic acid anilides according to the present invention are those, in which R1 represents a hydrGger ator or a straight-chain or branched alkyl radical having 1 to 4 carbon atoms;
R2 represents a hydrogen ator, a straight-chain or branched alkyl radical having 1 to 4 carbGn ator.s, an alkcxy rzdical having 1 tc 4 carkon atoms, a hydroxyalkyl radical having 1 to 4 carbQn atoms, an alkoxyalkyl radical having 1 to 4 carbon atoms in the alkyl part and 1 to 4 carbon atoms in the alkoxy part, cr a benzyl radical;
R3 represents a hydrogen ator~, a strai~ht-chain or branched alkyl radical having 1 to 4 carbon atoms 3 an alkoxy radical having 1 to 4 carcon atorls, an alkoxyalkyl radical having 1 to 4 carbon ator,s in the alkyl part and 1 to 4 carbon atoms in the alkoxy part, an alkylcarbonyl radical having 1 to 4 carbon atoms in the alkyl part, an alkylcarbonyl-alkyl radical having 1 to 4 carbon atoms in each alkyl part, an alkcxycarbonyl radical having 1 to 4 Le A 21 262 ., ~

fl carbon atoms in t~e alkGxy part, an alkoxycarboryl-alkyl radical having 1 to 4 carbon atoms ir. the alkoxy part ar.d 1 to 4 carbon atoms in the alkyl part, or a straight chain or branched alker.yl radical having 2 to 6 carbon atoms; or Rl and R2 tcgether with the C=C double bond~
represent an opticnally monosubstituted cr poly-substituted, monounsaturated or polyunsaturated, 5-membere^d or 6-membered ring which can contair. 1 or 2 hetero ato~s (the following be~ng mentioned as exa~ples of substituents: alkyl having 1 to 4 carbon atoms, halogen and hydroxyl); or R2 and R3, together with the adjacent carbon atGms, represent an o~tionally ~onosubstituted cr poly-substituted, saturated or unsaturated, 5-merbered or 6-membered ring l~-hich car cortain one or two hetero atoms (the following being mentioned as examples of substituents: alkyl having 1 to L
carbon atoms, halogen and h~droxyl~; or R2 and R3 tcgether represent a radical of the gereral formula ~ R~
\ R7 wherein R6 represerts a hydrogen atom cr an alkyl radical having 1 to 4 carbon atoms and 2~ R represents an alkyl radical having 1 to 4 carbon atoms or a phenyl radical;
Xl, x2 ard X3 independently of one another represents a hydro~en atom, a strai~ht-chain or branched alhyl radical having 1 to 4 carbon atoms or a fluorine, chlorine or bro~ine atcm;
Y represents a furyl, tetrahydrofuryl, thienyl or tetrahydrothier.yl radical, an optionally substituted phenyl radical (the following being mentioned as Le A 21 26~
., __. ..

preferred substituents: halcgen, alkyl, alkcxy and alkylthiG, each having 1 to 4 carbGn ato~.s, halo-genoalkyl, halogenoalkoxy and halogenoal~ylthio~
each having 1 to 4 carbon aton,s and 1 to 5 identical or different haloger. atoms, such as flucrine ato~s and chlorine aton.s, nitro and cyaro, and phenyl which is optionally subs~ituted by halogen and alkyl havlng 1 to 4 carbon atoms)g an iso~azolyl radical which is optionally substituted by nlethyl or ethyl, a 1,2,4-triazol-1-yl, imidazol~l-yl or p~Jrazol-l-yl radical, an alkyl radical which has 1 to 4 carbon ato~,s and is cptionally substituted by cyano cr thiocyanc, an alkenyl or alkiryl radical, each having 2 to 4 carbon atonl.s, ar. optionally sub-stituted cyclcalkyl radical having 3 to 7 carbon atoms or an optionally substituted cycloal~enyl radical having L~ to 7 carbon atoms (the following being preferred substituents cn the cycloalkyl or cyclo~
alkenyl radical alkyl having 1 to 4 carbon aton~.s, alkenyl having 2 to 4 carbon atoms, halogerloalkyl havirlg 1 to 4 carbon atom3 and up to 5 identical or different halogen atoms; halogenoalkenyl having 2 to 4 carbon atoms ar.d up to 5 identical or different halogen atoms, ~alogen, alkoxy having 1 to 4 carbon atoms ar.d a 2-membered to 5-nen.berea ~lethylene bridge), a dihalogenoal~.yl radical having 1 or 2 carbon atoms (fluorine, chlorine and brc~.ine being mentioned as preferred halogen atons), or a groupirg of the general formula -CH2A, -CH2R9, -CH20R , -CH20R9~ -CH2SR
-CH2sR ~ ~CH2-~OnR , -cH2sonR~ -CH20sclR8 -CH2CsGR9, -CH2CS02R, -CH20~02R9, -CH2~cOR ~
-CH20COR9, -CR8, -CR9, -SR8~ -SR9, -NRlORll, Le A 21 262 in ~hich R8 represent~ an cption~lly halcgen-su~stituted (in particular by fluorine, e~ilorine or brcmine)g cyano-substituted or thiocyano-su~stituted al~yl radical having 1 to L, carbon aton~s, an alkenyl or alkir.yl radical, each having 2 to 4 carbon atorns, or an alkoxyalkyl radical having 1 to 4 earbon aton.s in eaeh alkyl part;
R' represents an optionally substituted phenyl radieal (preferred phenyl substituents bein~ those already mentioned in the case of Y);
Rl~ and Rll independerltly of e~e~ other represent a hydrogen atom~ an alkyl radlcal having 1 to 4 carbon atoms, an alkenyl radical having 2 to 4 carbon atoms or an optionally substituted phenyl radical (preferred phenyl substituents being those already rnentioned in the ease of Y);
Az represents a pyrazol-l-yl, 1,2,4-triazol-1-yl cr imidazol 1 yl radical, and n is 1 or 2.
Partieularly preferred con.pounas of the preser.t in~ention are those in ~hieh Rl represents a hydrogen atcm or a niethyl, ethyl or isopropyl radieal, R represents a hydrcgen atom or a methyl, ethyl, isopropyl, rnethoxy, ethcxy, isopropcxy, methoxyrnleth~l, ethoxy~ethyl, hydroxyisopropyl or benzyl radieal~
R3 represents a hydrcger atom, or a methyl, ethyl~
isopropyl, methoxy~ ethcxy, isopropcxy, methoxy-methyl, ethoxymethyl, methylcarbonyl, ethylcarbonyl, niethylcarbonylmethyl, n!ethcxycarbcnyl, ethoxy earbonyl or methoxyearbonylnlethyi radieal or a straight-chain or branehed alkenyl radical having 2 to 4 carbon atoms, or Le ~ 21 262 /~
pl ar.d R , together with thé C=C dcuble bond, represent a morounsaturated or polyursturated 5-membered or 6-membered ring which is optionclly substltuted by methyl, ethyl, hydrcxyl and/or chlorine, and which can contain one or two heterc atoms (such as, especially, oxygen, r.itrogen or sulphur), or R2 and R3, together with the adjacent carbon 2tcm~
represent a saturatec or unsaturated 5-memberea cr 6-~embered rin~ which is optionally substltuted by methyl, ethyl, hydrcxyl and/Gr chlorine, and whic can contain one or two heterc atoms (such as, especially, oxygen, nitrogen Gr sulphur), or R and R3 together represent a radical of the general for~ula ~ R6 3 \ R7 wherein R6 represents a hydrogen atom or a methyl or ethyl radicalg R7 represents a methyl, ethyl or phenyl r~dical, xl represents G hydrcgen atcm cr a methyl, ethyl, isopropyl, iscbutyl~ sec.-butyl Gr tert.-butyl radical or a chlorine or fluorire ato~, x2 represer.ts a hydrc~en atom, 2 methyl, ethyl, isopropyl, iso~utyl, sec.-butyl cr tert.-butyl radical cr a chlorir.e or fluorir.e acom3 X3 represents a hydroger. atom, a methyl, ethyl~
isopropyl, iso~utyl, sec.-butyl or tert.-butyl radical or a chlorire or fluorine atom, 3G Y represents a fur-2-yl, thien-2-yl or tetrahydrG-fur-2-yl radical, a phenyl radical which is option-ally substituted by fluorine, chlorine, ~ethyl, methoxy, methylthio, trifluoromethyl~ trifluoro-~lethoxy, trifluorcmethylthio, nikro, cyano, phenyl -L-e A 21 -262 ~1 and/or chloropher.yl,a 5-methylisox2zol~3-ylg pyrazol-l-yl, 1,2,4-triazol-1-yl or imidazol-l-yl radical, an optionally cyano-substituted methyl, ethyl, allyl or propargyl radical, a cyclopropylg cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl or cyclcheptenyl radical, each of which can be substituted by methyl, ethyl, vinyl, allyl, fluorine, chlorineg chloro-methyl, trifluoromethyl, dichlorovinyl, methoxy or trimethylene, a dichloromethyl radical cr a grcuping of the general formula -C~2Az, -CH2GR8, -CH20R9, -CH2SR8j -CH2SR9, 2S90nR, CH2S80nR ~ -C~20SC2R8, -CH20s02R
-CH2R , -CH2GCOR , -CH20CCR9, -OR ~ -OR , -SR8, -SR9 or -NRlORll, in which R8 represents a methyl, ethyl, allyl, propyl, pro-pargyl, methoxymethyl, ethoxymethyl or et~.cxyethyl radical, R9 represents an optionally substituted phenyl radical (suitable substituents being, especially, those already rentioned in the case of Y), R10 and Rll are identical or different and represent a hydrogen atom, a methyl, ethylg i~opropyl, vinyl or allyl radical cr a phenyl radical ~hich is option-ally substituted by fluorine, chlorine, ~ethyl, r,ethoxy, methylthio and/or trifluorcmethyl~and Az and n have the meaning given imredi2tely abo~Je.
Especially preferred cor,pcunds accorcing to the 0 present invention include the compounds
3 , CH=CH2 ~/ \~ N
-COCI~20C~3 C~3 and Le A- 21 262 " c~-i3 \ C OC H2 - N~

In addition to the co~ipounds mentioned in the preparative Exa~ples, the fol'owin~ co~pounds Gf the ~eneral for~.ula (I) may 'c~e ~.enti.cned individually:
Rl R2 x2 ~ \C - C / (I) X1 x2 X3 -CRl-CR2R3 H 2-CH3 6-CH3 -C(CH3)=CH2 -CH2 ~

H 2-CH3 6-~H3 -C(CH3)=CH2 -CH2-SCH3 H 2-CH3 6-CH3 -C(CH3j=CH2 -CH2-SO-CH3 2-CH3 6-CH3 -C(CH3)=CH2 -CH2-SO2-CH3 H 2-CH3 6-CH3 -C(CH3)=CH2 -CH2-SCN

H 2-CH3 6-CH3 -C(CH3)-CH2 -CH2-O-H 7.-CH3 6-CH3 ~ ~

H 2-CH3 6-CH3 -C(CH3) =CH2 ~ -CF3 Le A 21 262 1 2 3 1_, 2 3 X . X. . X . . .. -CR -C~ R. .. .... . ~ ...
~== N
H 2-C1 6-CH3 ~ -CH2~

H 2-CH3 6-CH3-C~ ~ -CH20CH3 f=~N
H 2-CH3 6-CH3 ~ -CH2~
4-CH3 2-CH3 6-CH3 ~ -CH20CH3 H 2-CH3 6-CH3-IC=cH2 -CH20CH3 ~ C(CH3)3 ~N =
H _2-CH3 6-CH3 -IC=cH2 -CH2 N N
C(CH3)3 H 2-CH3 6-CH3 -~=CH2 -CH20CH3 C(CH3)3 H 2-CH3 6-CH3 -CH=CH-C2~1s -CH20CH3 2~CH3 6-CH3 -CH=CH ~ C~13 CH2 ,~N

If, for exam~le, N-iscprcpylidene-2,6-dimethyl-aniline and ~ethoxyacetyl chloride ~re used as starting materials, the course of reaction variant (a) acccrdlng to the present invention is illustrated by the ,ollo~iir.g equation:

Le A 21 262 C~l CH3 C(CH3) CH3 N=C + CH30CH2COCl - ~ CH3 CO-CH20CH3 CH3 / C = CH2 (Base) ~ ~ N
- HCl CH3 CO-CH20CH3 Ifj for examp'e, ~-chlorccarbonJ-l-N-(l-~ethyl-vinyl)-2,6-dimethylaniline and 1,2,4-triazole are used as starting ~aterials, the course of reaction variant (b) according to the present invention is illustrated by the following equation:
c\3 CH3 CH3 C = CH2 /==N Base r-~CH3/ C = CH2 CH \ CO Cl N ~ -HCl ~ ~CH \ CO-N ~
If, for exa~.ple, ~T~chloroacetyl-N~ methylvirlyl)-2~6-dimethylaniline and pyrazole are used as starting ~.aterials, the course of rezctlorl variant (c) acccrding to the present invention is illustrated by the fol~owin~
equation:

N \ ;l N-~ -HCl ~ H3 CO C -N

If, for example, N-hyclroxyacetyl~ in~1-2~6-di~.ethylaniline and ~.ethanesulphon~Jl chloride are usedas startin~ materials, the course cf reactlon variznt (d) ac~ording to the preser.t invention is illustrated by the following equation:

Le A 21 262 ~L 4~

CH3 CH = CH2 , Base N \ + CH3502Cl ~~
CH3 `CO-CH20H
CH3~ CH = C~l2 -N

Ifg for example, 1 mol of N-r.,ethylthioacetyl-M-vinyl-2,6-dimethylaniline and 2 mol o~ m-chloroperbenzcic acid ~re used as start-~ng ~.aterials~ the course of the react-ion variank (e) according to the present inventiGn is illus-trated by the following equation:
CH3 ,CH = CH2 , ~ 2 ~ CO-OOH
N \ --CH3 CO-CH25CH3 CH ~ CH = CH~
N \
CH3 CO-CH2-502-cH3 Preferred azines of forr..ula (IT) to be used as starting r.aterials for reacticn v~riant (a) according to the invention are those in ~,vhich ~1, Xl, x2 and X3 represer.t those radicals ~lhich have already been ~entioned fc~ these substituents in connection with the description of the preferred ard partic-ularly preferred ccmpound acccrding to the precert inventicn, R4 represents a hydrogen atcr9 a straight-chain or branched 21kyl radical having 1 to 4 carbon atcr.s, an alkoxy radical having 1 to 4 carbon atorr.s9 a hydroxyalkyl radical having 1 to 4 carbon ator~s, an alkoxyalkyl radical having 1 to ll carbcn ator.~s in the alkyl pa.rt and ]. to 4 carbon ators in the alk ocy part, or a benzyl radical~
R5 represents a hydrcgen atom, a straight-chain or branched alkyl radical having 1 to 4 carbcn atGrLs, an alkoxy radical having 1 to ~ carbon ator;ls, an Le A 21 262 ~_, /~
- ~7 ~
alkoxyalkyl racical lavin~ 1 to 4 carbon atoms in the 21kyl part ard 1 to 4 carbon a~oms in the al~oxy part, an alkylcarbonyl radical ~laving 1 to 4 carbon atoms in the alkyl ~art3 an al~ylcarbonylalkyl rad-ical having 1 to 4 carbon atoms in each alkyl part, an alkcxycarbonyl radical having 1 to 4 carbon atoms in the al~oxy part, an alkoxycarbonylalkyl racical having 1 to 4 car~on atoms in the alkoxy part and 1 to 4 carbon atoms in the alkyl part, or a straight-chain or branched al~enyl radical having 2 to 6 carbon atomls, or Rl and R4, together with the adjacent C-C bond, also represent an optionally monosubstituted cr polysubstituted, saturated or unsaturatec 5-membered or 6-membered ring which can contain one or two hetero atoms (trle following being mentioned as examples of substituents: alkyl having 1 to 4 carbon atoms, halogen and hydroxyl), or R4 and R5, toget~er with the adjacent carbon atGm, also represent an optionally monosubstituted or poly-substituted, saturated or unsaturated 5-membered or 6-r~e~lbered ring which can contain one or two hetero atoms (the following being mentioned as ex~mples of substituents: alhyl having 1 to 4 carbon atoms, halogen and hydro~yl), or R4 and R5 tcgether also represert a radical of the formula 6 R
=C
\ R7 wherein R6 represents a hydrogen ator. or an alkyl radical having 1 to 4 carbon atoms and R7 represents an alkyl radical having 1 to 4 car~cn atoms, or a phenyl radical~

Le A 21 262 The azines of the formula (II~ are known or can be prepared in a simple manner by processes which are known in principle (see DE-OS (German Published Specification) 1,670,859 and DE-OS IGerman Published ~pecification) 3,011,084~.
Preferred acid derivatives of formula (III) additionally to be used as starting materials for reaction variant (a) according to the present invention are those in which Y represents those radicals which have already been mentioned for this substituent in connection with the description of the preferred and particularly preferred compounds according to the present invention~
The acid derivatives of the formula (III~ are known com-pounds of organic chemistry, or can be obtained in the customary manner.
Preferred carbamic acid-chlorides of formula ~V) to be used as starting materials in carrying out reaction varian-t (b) according to the present invention are those in which Rl, R2/ R3, Xl, x2 and X3 represent those radicals which have already been mentioned for these substituents in connection with the description of the preferred and particularly preferred compounds according to the present invention.
The carbamic acid-chlorides of the formula (V) are not yet ~nown. They are obtained by reacting azines of the formula (II) with phosgene, according to reaction variant (a).
Preferred compounds of formula (-~I) additionally to be used as starting materials for reaction variant (b) according to the invention are -those in which Az represents those radicals whlch have already been mentioned for this substituent in connection with - 17 ~

the description oE the preferred and particularly preferred compounds according to the present invention, and B represents a hydrogen atom, sodium or potassium.
The compounds of the formula (VI) are generally known compounds of organic chemistry.
Preferred chloroacetamides of formula (VII) to be used as starting materials in carrying out reaction variant ~c) accord-ing to the invention are those in which R , R , R , X , X and X3 represent those radicals which have already been mentioned for these substituents in connection with the description of the pre-ferred and particularly preferred compounds according to the presen-t invention.
The chloroacetamides of the formula (VII) can be obtained by reacting azines of the ~ormula (II~ with chloroacetyl halides, according to the process condltions mentioned for reaction variant (a).
Preferred compounds of formula (VIII) additionally to be used as starting materials for reaction variant ~c) according to the invention are those in which ~z and R8 represent those radicals which have already been mentioned for -these substituents in con-nection with the description of the preferred and particularly preferred compounds according to the present invention, and B
represents a hvdrogen atom or sodium or potassium.
The compounds of the formu]a (VIII) are generally known compounds o organic chemistry.
Preferred hydroxyacetanilides of formula (IX~ to be used as starting materials in carrying out reaction variant (d) according to the inven-tion are those in which R1, R2, R3, Xl, ~2 and X3 represent those radicals which have already been mentioned for these substituents in connection wi-th -the description of the preferred and particularly preferred compounds according to the present ~3 `~

invention.
T~,e ~Iydrcxyacetar.ilides cf the forrnula (IX) are not yet known, but can be cbtained in a generally known manner by hydrolysing a acyloxyacetyl-ani.lideg which is a compound accordir.~ to the present invention of the formula Rl R2 \ / C - C (XII) X2 ~ N \ \R3 X3~- C0-CH2-OCOR12 in ~-hich Rl, R2, R3g Xl, x2 and X3 have the same meanirgs as in f`ormula (I) and Rl2 represents an alkyl radical having 1 to 4 carbcn atoms~
with sodium hydroxide solution or potassium hydroxide solution~ or with an alkali metal alcohclate o~ a lower alcohol (such as sodium methylate or sodiuni ethylate) at 15 a temperâture bet~Teen 20 and 40C~ and, after ac-difying the mixture in the customary manner, isolating the compound of the for~lula (IX).
Preferred halides of formula (X) additionally to be used as starting materials for reacticn variant (d) acccrd-20 in~ to the present i.nvention are thcse in Ti~Thich R8 and R9 represent those r~dicals 1~ihich have already been ~entioned for this substituent in conrection with the description of the preferred and particularly preferred ccmpounds according to the present ~nvention.
The halides cf the forrnula (~) are gererally knol~Tr compounds of organic ch~m.istry.
The acetanilides cf the formula (XI) to be used as starting materials in cGrrying out reaction variarlt (e) accordinG to the invention, are compounds according to the 3 present in~Tention.
The oxidation of reactiGn variant (e) accordin~ to Le A 21 262 the invention is effected by reaction ~ith custcmary inorganic or organic oxidisinG a~ents. mhe~e include, as preferences, crganic per-aci~s (such as peracetic acid, p-nitroperbenzoic acid, ar.d m-chlcrGperbenzoic acid), inorganlc per-acids (such as periodic acid) and further-more hydrogen peroxide in glacial acetic acid or rrethanol.
Inert crganic solvents are suitable diluents ~or reaction variant (a) acccrdin~ to the in~rention. These include, as preferer.ces~ ketones (such as acetone and rr.ethy].
ethyl ketone), nitriles (such as 2ceton-trile), ethers (such as tetrahydrofuran or dioxane), esters (such as ethyl acetate)~ halcgenated hydrocarbons (such as methylene chloride) and, especially, aromatic hydrocarbons (such as toluene and benzene).
In carryin~ out reaction variant (a) according to the invention~ the reaction terr.peratures can be varied within a relatively wide ran~e. In general~ the reaction is carried out at a temperature between -20 and +150C, prefer-ably between -20 and +100C.
The eliminatior. of hydrogen halide ir. reaction variant (a) accordin~ to the invention is effected in a generally custcrr.ary and known m2nner, for exarple by heating the reacticn mixture under reflu~ or by the addition of a base at the abcverrentior.ed terr.peratures.
~5 Any of the inor~anic or or~anic acid acceptors which can customarily be used can be errployed as the base.
These preferably include alkali metal carbonates (such as sodiu~. carbonate and potassiu~ carbcnate or sodiurr. bicar-bonate), ar.~ al~o lower tertiary alkylarrlines, aralkyl-3 a~ines, aromatic amines cr cycloalkylarî!ires (such as, for example, triethylamine, dimethylbenzylarrir.e, pyridire, 1,5-diazabicyclo-~4.3.0]-non-5-ene (~BN) and 1,8-diaza-bicyclo~[5.4.0]-undec-7-ene (~BU)). ~:owever, it is also possible to err.ploy ~n a~propriate excess of an azine 3~ of the for~nula (II).

Le A 21_?62 Equimclar ar,1ounts are preferablJ used 1~hen carrying out reaction variant (G) accordîng tc the invention.
The isolation Gf the end products is effected in a gererally customary manr.er.
Inert crganic sclvents are preferred diluents for reaction variants (b) and (c) acccrding to the invention.
These include~ as preferenceg ketones (such a~ diethyl ketone~ in particular acetone and methyl ethyl ~setone), nitriles (such as propionitrile, in particular acetonitri'e)~
ethers ~such as tetrahydrofuran or dioxane) 3 aliphatic and aromatic hydrocarbons (such as petroleum ether, benrene, toluene or xylene), halcgenated hydrocarbons (such as methylene chloride, carbon tetrachloride, chloroform or chloroben~ene), esters (such as ethyl acetate) and formam-ides (such as, especially, dimethylformamide).
Reaction variants (b) and (c) according to theinvention can be carried out, if appropriate, in the pres-ence of acid-bindir.g agents. m~ he custcmary acid-binding agents can be used as the acid-bindirg agent. These include, as preferences, t~e substances alr~ady mentioned for reaction variart (a). If appropriate, an excess of the azole can also be used.
Ir. reaction variants (b) and (c), the reaction temperatures can be varied ~ithin a relatively wide rarge.
In general, the reaction is carried out at a temperature between 20 and 150CC, preferably bet~Jeen 6C and 120C.
I~hen a diluent is present, the reacticn is advantagecusly carried out at the boiling poin of the particular diluent.
In carrying out reaction variants (b) and (c) according to the lnvention, about 1 to 2 mol of the com-pounds of the for~lulae (V ) or (VIII) and, if appropriate, about 1 to 2 mol of an acid-binding a~ent are preferably employed per mol of the compounds of the formulae (V) or (VII). The isolation o the compounds of the formula (I) is effected in a CllS tomary ~annerl.

Le A 21 262 Inert crganic sclvents are preferred diluents for reaction variant (d) according to the invention. These preferably include t~e solvents already mer.tioned for re-actior~ variant (b).
The reaction according to reaction variant (d) can be carried out, if appropriate~ in the presence of an acid-binding a~ent. Any of the inorganic or organic acid-bind-ing agents which can custcraril~J be used can be added.
These ir.clu~e, as preference, the compounds already men~
ticned for reaction variant (a).
In reaction variar.t (d), the reaction temperatures can be varied within a relatively wide range. In general, the reaction is carried out at a terr;perature between 20 and 150C, preferably at the boiling point of the partic-ular diluent5 for example at from 60 to lCCC.
In carrying out reaction variart (d) acccrdingto the inventior, 1 mol of the halide o~ the formula (X) and~ if appropriate, from 1 to 2 mol of an acid-binding agerlt are employed per r.ol of the compounds of the for~iula (IX), if appropriate after the additicn of frorr. 1 to 2 mol of a strong base (such as an alkali metal hydride).
Tc isolate the end products, the reaction mixture is freed from the solvent, ar.d water and an organic solven~ are added to the residue. The organic phase is separated off and worked up in the custorrary rlanner.
According to a preferred embodir!ent of reactior variant (d), the process is advantageously carried out as follows: a hydrcxyacetanilide of the formula (IX) is used as the starting co~pound~ and is convertcd into the alkali metal alkanGlate in a suitable solvent~ by means of an alkali metal hydride or alkali metal bromide, and the alkanolate, without being isolated, is immediately reacted with a halide of the formula (X), alkali metal halide being split off to give the compounds according to the invention, of the formula (I), in one operation.

Le A 21 262 Inert or~anic solvents are preferred diluents for reacticn variant (e) according to the invention. These irclude~ as preferences, ketones (such as diethyl ketone, especially acetone and methyl isG~utyl ketor.e), nitriles (such as propionitrile, especially acetonitrile), ethers (such as tetrah~-drofuran cr dioxane), aliphatic and aromatic hydrocarbGns (such as petroleum ether, benzene, toluene or xylene), hâlogenated hydrocarbcns (such as methylene chloride, carbcn tetrachloride9 chloroform or chlorobenzene), esters (such as ethyl acetate), alcohols (such as methanol) ar.d carboxylic acids (such as acetic 2C id).
In carrying out the oxidatiorl accordin~ to reactlon variant (e)~ the reacticn temperatures can be varied within a relatively wide rar.~e. In general, the reaction is carried out at a temperature bet~-een ~2C and 40C, prefer~
ably between -10 and +30C.
In carrying out the oxidation of reactiGn variant (e), 1 or 2 mol of oxidi~ing agent are employed per mol of the compounds according to the invention, of the formula (XI). ~hen 1 mol of an oxidising agent (such as m-chloroperbenzoic acid in ~.ethylene chloride) is used, at a temperature bet~een -2C and +2CC, corr.pounds according to the invention, of the formula (I), ~lith n = 1 are preferentially forrred. ~ith 2 rr.ol of the oxidising agert and higher temperatures (0 to 40C), ccmpounds acccrding to the invention, of the formula (I), ~Tith n = 2 are prefer-entially forrrled. The isolaticn of the oxidation prcducts is effected in the custorrary mannerO
l1!hen Y = Az and -CH2-Az, the compounds prepared according to reaction variant (a), (b) or (c) of the forrr.ula (I) can be converted, if desired, into the acid addition salts or metal salt corrlplexes.
The follo~AIing acid~ are preferred for the pre-paration of ph~siologicall~; tolerated acic addition salts Le A 21 262 ..

of the ccmpounds of the formula (I): hydrohalic acids (such as hydrobromic acid and, especially, hydrcchloric acid), phosp~orlc acid, nitric acid, sulphuric acid, monofunctional and bifunctional carboxylic acids and hydroxycarboxylic acids (such as acetic acid, maleic acid, succinic acid, scrbic acld and lactic acid) and sulphonic acids (such as p-toluenesulphonic acid and naphthalene-1,5-disulphonic acid).
The acid addition salts cf the compounds of the formula (I) can be obtained in a simple manner according to customary methGds of salt formation, for example ~y dissolving a compound of the formula (I) in a suitable inert solvert and adding the acid, ard can be isolated in a known manner, for exar.ple, by filtering, and can be purified, if appropriate, by washing with an inert organic solvent.
~ or the preparat on of metal salt cor.plexes of the compounds of the formula (I), salts of metals of main groups II to IV and of sub-groups I ar.d II and ~ to VIII of t~e Periodic Table according to Mendeleev are pre-ferred, copper~ zinc, mar.ganese, magnesium, tin, iron and nickel being mentioned as examples.
Possible anions of the salts are thcse ~lhich are preferably derived from the follcwing acids: hydrohalic acids (such as hydrochloric acid ard hydrcbromic acid), phosphoric acid, nitric acid and suiphuric acid.
The metal salt complexes of the compounds of the formula (I) can be obtained in a simple manner by customary processes, thus, for example, by dissolving t~.e metal salt 3~ in an alcohol, for example, ethanol, and adding the solution to compounds of the formula (I). The metal salt complexes can be isolated in a ~:nol~n manner, for ex-ample by filtraticn, and if appropriate purified by recrystallisation.
The active compounds accor~ing to the invention Le_A 21 262 t~
~.~.;i, ~ ~ 9 exhibit a po~erful microbicidal action and can be er.ployed in practice for corbating ur.desired micrc-crganis~,s.
The active compcunds are suitable for use ~.s plant protection a~ents.
~ur.gicidal agents in plant protection are employed for combating PlasmcdiophGromycetes, Comycetes, Chytridio-mycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
- The good tolerat on, by plants, of the active com~
pounds, at the concentratiGns required ~Gr ccmbating pl~.nt dise~ses, permits treatment of above-ground parts of plants, of vegetative propagation stock and seeds, and of the soil.
As plant prot~ction agents, the active ccr.pounds according to the invention can be used with particularly ~ood success for combating Oorycetes, for example against the blight and late blight of tomato and potato causative organism (Phytophthora irfestans). The fact that the actiue compounds according to the invention disclose not only a protective action but also a syste~.ic action should be emphasised. Thus, plants can be protected against attack by fungi when the active compound is fed, TJia the soil and the root or via the seed, to the above-grcund parts of plants. ~l~hen used in apprcpriate a~cunts, the compounds accGrding to the invention also exhibit herbicidal and plant growth-regulating prcperties, and an action against hygiere pests and pests cf stored products.
The active co~pounds can be converted to the cus-tomary formulations, such as solutions, emulsions, ~ettable powders, suspensions, powders, dusting agents, foams, pastes, soluble powders, granules, aercscls, suspension-emulsior concentrates, seed-treatment powders, natural and synthetic materials impregrated with active cc~pcund, very fine capsules in poly~eric substarces and in coating com positions for seed, and formulatior.s used T,lith burning Le A 21 262 -equipment, such as fumigating cartridges, fumigating cans and fumigating coils 3 as well as ULV cold mist and warm rrst formulations.
These fcrmulaticns m2y be produced in kncwn manner, for example by mixing the active compounds with e~tenders, that is to say liauid or liquefied gaseous or solid diluerts or carriers, optionally with the use of surface-active agents, that is to say er.ulsifying agents and/or dispersing agents and/or foam-forming agents. In the case of the use of water as an extender, organic solvents can, for example, also be used as auxiliary solvents.
As liquid diluents or carriers, especially solver.ts, there are suitable in the main, aromatic hydrocarbons, such as xylene, tcluene or alkyl naphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons~ such as chlorobenzenes, chloroethylernes or methylene chloride, aliphatic or alicyclic hydrocarbons, such as cyclohexane or paraffins3 for example mineral oil fracticns, alcohols, such as butanol or glycol as well as their ethers and esters, ke~ones, such as acetone, rethyl ethyl ketone~
methyl isobutyl ketone or cyclohex2none, or strongly polar solvents, such as dimethylformamide and dimethyl-sulphoxide, as well as water.
By liquefied gaseous diluents or carriers are r.eant liquids which would be gaseous at norr.al te~.perature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons as well as butane, propane~ nitrogen and carbon dioxide~
As solid carriers there may be used grcund natural 3o minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, mont~crillonite cr di~tomaceous e2rth, and ground synthetic minerals, such as highly dlspersed silicic acid, alumina and silicates. As solid carriers for granules there may be used crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite Le A 21 262 and dolomite, 2S well as synthetic granules cf inorganic and organic meals, and granules of crganic mater al such as sawdust, coconut shells, maize cobs and tobacco stal~s.
As emulsifying and/or foam-for~ir.g agents there ma~ be used non-ionic and anionic emulsifiers, such as polyo~:yethylene-fatty acid esters, polycxyet~.ylere-fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulphonates, all~yl sulphates 3 aryl sulphonates as well as albumin hydrolysis prcducts. Dispersing agents include, fcr e~ample 3 lignin sulphite wa~te liquors and methylcellulose.
Adhesives such as carbcxymethylcellulose and natural and synthetic poly~Lers in the rorm of powders, granules or latices, such as gum arabic, polyvinyl alcchol and polyvinyl acetate, can be used in the formulations It is possible to use colorants such as incrganic pigments, for e~ample iron oxide, titanium oxide and Prussian Blueg and orgarlic d~estuffs, such as alizarin dyestuffs, azo dyestuffs or metal phthalocyanine dyestuffs, and trace nutrients, such as salts of iron, mangarese, boron, copper, cobalt, molybdenum and zinc.
The formulations in general cortain from C.l to 95 per cent by weight cf active ccmpound, preferably from 0.5 to 90 per cent b~- ~ieight.
The active compounds accordir.g to the invention can be present in the forr.ulations or in the various use forms as a mi~ture with o~her known active compounds, such as fungicides, bactericides, insecticides, acari-cides, nematicides, herbicides, bird repellarts, growth factors, plant nutrients and agents for improving soil structure.
The active compounds can be used as such cr in the for~l of their formulations Gr the use forms prepared therefrom by further diluticn, such as ready-to-use solutions, ernulsions, suspensions, pcwders, pastes and .

Le A 21 262 granules. They are used in the customary manr.er~ fcr example by ~1aterir.g, i~.ersion, sprayirg, ator:ising, misting, vaporising, injec-ting, forming a slurry, brush-ing on, dusting, scattering, dry dressing, mGiSt dressing, wet dressing, slurry dressing or encrustirg.
Especially ln the treatmer.t of parts of plarlts, the active compound concentrations in the use forms can be varied within a substantial range. They are, in general~
between 1 and 0.0001% by weight, preferably betweer. G.5 and o.oO1~-In the treatment of seed, anounts of active com-pound of 0.001 to ~0 g per kilogram of seed~ preferably C.C1 to 10 g, are generall;- required.
For the treat~ent cf soil, active compound con-centrations of O.CC001 to 0.1% by weight, preferably0.0001 to 0.02%~ are generally required at the place of action.
The present invention also prov,des fungicidal ccmposition cGntaini.ng as active ingredient a ccmpound cf the present invention in admixture with a solid or liquefied gaseGus diluent or carrier or in admixture with a liq~id diluent cr carrier cor.taining a surface-active agent.
The present invention alsG prGvides G method O~ combatlng fungi which comprises applyin~ to the fungi, or to a habitat thereof, a compound c~ the present inventiGn alone or in the form of a composition cor.taining as active ingredient a compound cf the present inver.tion in admixture with a diluer.t or carrier.
3 The present inVentiGn further prov des cr~ps prctected from damage by fungi by being grown in areas in which immediately prior to and/Gr during the time of the growing a compound of the present invention was applied alcne or in admixture with a diluent or carrier.
` It will be seen that the usual methods of providir.g Le A 21 262 a harvested crcp rray be im~roved by the present invention.
Preparat ve Excmples . _ _ Example 1 C H 3
5 (Reaction variant (a)) 166 g (1 mol) of N-isopropylidene~-2~6-dilrlethyl-aniline, dissolved in 30C ml of toluene, were added drGp-wise to a soluticn of 115 g (1 mol) of methoxyacetyl chloride in 100 ml of toluene at 0C, while stirring~
10 The mixture was stirred for a further 2 hours at room temperature, and 152 g (1 mol) of 2,3,4,6,7,8,9,10-octa-hydro~[l,2,0]-azepine were then added dropwise at 0C.
The mixcure was stirred for a further 3 hours at 2CC and pGured into 2,0CC ml of d lute aqueGus bicarbcnate 15 solution, 500 ml of ethylacetate ~Jere cdded, ar.d the mixture was stirred until reaction WâS corplete. The organic phase was separated off, l,Jashed several tilrles with water and then evapcrated dG~Tn in L~CCUC . The residue w~s fractionally c'.istilled in a high vacuum.
20 136 g (58.4% of theory) of Ni-methoxyacetyl-N~ ethylvinyl)-2,6-dimethylaniiine were obtained in the fcrm of a colcur-less oil of boiling pcint 87 to ~C/0.4 rr!bar.
Pre~araticr. of the stL~r-tin~ materia~

~N = C(CH3)~

Ool g of p-toluenesul~honic acid was added to a ~nixture cf 121 g of` dirrethylaniline and 156 g (1.5 mol) of 2,2-dimethoxypropane, and the mixture was heated uncler reflux for 30 minutes. The Irethanol forred was then Le A 21 262 distilled off. To complete the reaction, a further 52 g (0.5 mol) of 2,2-dimethoxypropane and 0.05 g of p--toluenesulphonic acid were added, and the reaction mixture was distilled until the boil ing point of the 2,2-dimethoxypropane (83C) was reached. The remaining solution was evaporated down in vacuo. 157 g (97~ of theory) of N-isopropylidene-2,6-dime-thylanilide were ob-tained in the form of a colourless oil.

3~
,3,~
Example 6 CH3 ~C = CH2 ~N~ /=N (6) CH3 CO - N ¦

(Reaction variant (b)) 233 g (1 mol)~ of I~-chlorocarbony1-N-(l-methyl-5 vinyl)-2,6-dimethylaniline, dissolved in lC0 rr.l cf dimethyl-formamide, were added drcpwise to a mixture of 69 g (1 mol) of 1,2,4-triazole and 138 g (1 ~ol) of potassium carbon-ate in 500 Irl of dimethylformalride at 2GC. ~he Ir.ixture was stirred for a further 2 hours av 8CC and was then 10 poured onto 2 kg of iCe. The solid which was precipitated in the process was filtered off and recrystallised fronm petroleum ether. 102 g (79.6% of theory) of M-(l-methylvinyl)-N-(1,2,4-triazol-1-yl-carbonyl)-2,6-dimethyl-aniline were obtained in the form of colourless crystals 15 of melting point 65C.
Prepara~ic-n of s_artir.g r,l.a~erial ~H3 CH3 / C = CH2 (~ \ CO - Cl 49.5 g (0.5 7l~01) of phosgene were passed irto a solution of 161.2 g (1 7r~cl) of M-isopropylidene-2,6-20 dimethylaniline in 500 ml of toluer.e at 0C, while stirring.The m.ixture was then stirred fcr a further 2 hours at 2CC, excess phosgene was expelled by passing ir. nitrogen, and the mixture was then filtered off under suction from the precipitate which was separated out. The filtrate was 25 evaporated down _n vacuc, and the residue frcm evaporation was fractionally dlstilled in a high vacuum. 107 g (C6~i cf t~eory) of N-chlorocarbonyl-M-(l-methylvinyl)-~,6-dimethyl-. .
Le A 21 262 ^:, ,~ .

aniline were obtained in the form of a colourless oil ofboiling point 85C/0.3 mbar.

Example 8 Cll /CH (8, (Reaction variant (c)) 119 g (1 mol) of N-chloroacetyl-N-(l-methylvinyl)-2,6-dimethylaniline, dissolved in 100 ml of dimethylformamide, were added dropwise to a mixture of 69 g (1 mol) of 1,2,4-triazole and 138 g (1 mol) of potassium carbonate in 500 ml of dimethyl formamide at 20C. This mixture was s-tirred for a further 2 hours at 80C, and was then poured onto 1 kg of ice. The precipitate which separated out in this process was filtered off, and re-crystal-3'~
~ ~6 -lised from ligroin. 90 g (66.7% of theory) of N~(l-methylvinyl)-~-(],2,4~triazol-1-yl-acetyl)-2,6-dimethyl-aniline were obtained in the form of colourless erystals of melting point 65C.
Pre~aration of the startin~ material ___ ______________________ _________ C~13 r_~CH3 / ~ = C~12 N
H3 C0 - CH2Cl 322.5 g (2 ~..ol) of N-isopro;cylidene-2,6-dimethyl-aniline were added drcp~Jise to a sGlution of 113 ~ (1 mol) of ehloroaeetyl chlcride in 100 ~1 of toluene, the tempera-ture being kept at 0CC. The mixture was then sti~redfor a further 3 hours at room te~perature. The mixture was filtered off from the precipitate which had separated out (N-isopropylidene-2,6-dimethylamine hydroehloride), and the filtrate was washed several times with bicarborate solution, and then T.~ith water. The organic phase was dried over sodium sulphate and evapcrated down in vacuo.
The residue was fractior.ally distilled in vacuo.
180.6 g (7670 of thecry) of ~-chlorGacetyl-M-(l-~ethyl-vinyl)-2,6~dimethylaniline were obtained as a cclourless oil of boiling poir.t 98 to 106C/C.15 mbar.
Example 9 CH3 ~ CH = CH2 ~CIl~ CO-CH20CH2C--CH (9) (Reaetion variant (c)) 2.3 g (0.1 mcl) cf sodium were 2.dded tG 50 ~r.l of propargyl alcohcl. After the evolution of hydrogen had ended~ 22.4 g (0.1 ~.cl) of ~T~ehlorcaeetyl-~l-vinyl-2,6-dimlethylaniline, dissolved n 50 ml of prop2rgyl alcohcl~

Le A 21 262 .

were added dropwise. The mix-ture was then stirred for a further 3 hours at 20C. The mixture was poured into methanol diluted with 1,000 ml of waterr and then extracted several times with ethyl acetate. The combined extracts were evaporated down ln vacuol and the residue was recrystallised from petroleum e~her. 13 g (53.5% of theory) of N-propargyloxyacetyl-N-vinyl-2,6-dimethylaniline were obtained in the form of colourless crystals of melting point 72C.

Example 12 ,CH3 N< C = CH2 (12) C~
3 CO - CH2 - N~ x 1/2 CuC12 .

(Metal salt complex formation) 1.7 g (0.01 mol) of copper (II) chloride dihydrate, dissolved in 50 ml of methanol, were added -to a solution of 5.4 g (0.02 mol) of N-(l-me-thylvinyl)-N (1,2,4-triazol-1-yl-acetyl)~2,6-dimethyl-aniline in 50 ml of methanol at 20C. The solution was evaporated clown ln vacuo, and -the residue was de-hydrated azeotropically several times by taking it up in toluene and then evaporating down the solution. The residue was recrystallised from carbon tetrachloride. 5 g (74.1~ of theory) of N~ methylvinyl)-N-(1,2,4-triazol-1-yl-acetyl)-2,6-dimethylaniline-copper (II) chloride were obtained in the form of slightly blue-coloured crystals of melting point 120C.

~; ~
~ i3 1 The compounds of the general formula (I) which are listed in Table 1 below could be obtained in an analogous , manner according to the process varian-ts given:
Table 1 Rl R2 3 - N < C - C \ (I) X CO - Y

NXo Xl x2 X3 -CR'=cR2R3 Y PhYSical 16 3 6 CH3 H -CH=CH2-CH2-OcH3 Bpo85C/

172 CH3 6-CH3 -CH=CH-Cll-cll2 -CH2ocH3 Mp:100C
L8 3 6 CH3 -C(CH3)=CH2N~-l Mp:88C

l9 3 6 CH3 -C(CH3)=CH2- ~ Mp:62 C

No X X3 cRl 2 3 Physical constant 2-CH3 6--CH3 ( 3) 2 H2 N~ Mp:55C

21 2-CH3 6-CH3 ( 3) CH2 2`~N P 6 22 2-CH3 6-CH3 H-CI-I- CH 2N/~ Bp:147C/
~-- 0.6mbar 23 2~CH3 6-CH3 H -CH=CH2 -CH2-N I Mp:122C

24 2-CH3 6-CH3 H-CH=CH2 CH2-N I Mp:85 C

2-CH3 6-CH3 H ( 3) CH2-CH2-N J Mp:155 C/
N N (xl/2 ZnC12) 26 2-CH3 6-CH3 ( 3) CH2 -CH2-N I Mp:205C/
\~F (xl/2 MnC12) 27 2-CH3 6-CH3 H -C(CH8)=CII2 -CI-I2OCH2C- CII Oil , Ex. 1 2 3 1 2 3 Physical No. X X X -CR =CR R Y constant .
28 2-CH3 6-CH3 H --CH=CH-C2H5 2 3 oil ~N
29 2--CH3 6-OEI3 H -CH=CH-C2H5 NI

2-CH 6-CH3 EI -CH-CH-CH=CH2 -N~N~ Mp:116C
/----N
31 2~CH3 6-OEI3 H -CH=CH-CH=CH2 -N ¦ Mpo112C
rN N O
32 C CH~ 6--CH3 H -CH=CH--CH=CH2 -N ¦ Mp:106 C

33 2-CH 6-CH3 H -C(C3H7 i)=CH2 -CH2OC~I3 Bp:150C/
N
34 2-CH3 6-CH3 H -C(C3H7-i~=CH2 -C~I2--N¦ oil N-~ ~-N
2~CH 6~CH3 ( 3) C 2 -N J oil 36 2-C1 6-CH3 H -C(CH3)=CH-C(CH3)=CH2 ~CH2OC 3 37 2-C1 6--CH3 H -C(cH3)=cH-c(cH3)=~H2 -N oil N

- 41 ~

Ex xl ~ ~ Y~ -CRl=CR2R3 ~ Y Physical f~N
38 2-Cl 6-CH3 H -C(cH3)=cH-c(cH3)=cH2 -N J oil ~=~N
39 2-C1 6-CH3 H -C(CH3)-CH-C(CH3) CH2 ~I oil 2-CH4-CH3 h-CH3 -C(cH3)=cH2 -CH20CH3 0.4 mbar . f=~N
41 2-CH3 3 H3 ( 3) 2 N oil 42 2-CH36-CH3 H -C(cH3)=cH-c(cH3)=cH2 -N I oil ~ ~N
43 2-CH6-CH3 H -C(cH3)=cH-c(cH3)=cH2 -N~ oil 44 2-CH 6~CH3 H -CH=CH2 -M I oil The fungicidal activity of the compour.ds cf this irvention is illustrated by the following biotest Examples.
In these Examples, the compounds accordin~ to the present invention are each identified by the rumber (given in brackets) of the corresponding preparative Example.
The known comparison compounds are identified as follows:
CH2-NH-CS-S ~
(A) ¦ Zn CH3 / I~H - CO - OC2Hs (B) ~N\
CH3 CO - CH2Cl Ex2mple A
Phytophthora Test (tomatG)/protective Solvent: 4.7 parts by wei~ht of acetone Emulsifier; 0.3 parts by weight of al~ylaryl polyglycol ether To produce a suitable preparat on of active com-pound, 1 part by weight of active compound was mixed withthe stated amounts of solvent and emulsifier, and the concentrate wes diluted with water to the desired concen-tration.
To test for protective activity, young plants ~ere sprayed with the preparation of active compound until dripping wet. After the spray coating had clriecl on, the plants were inoculated with an aqueous spore suspension of Phytophthora infestans.

Le A 21 262 ,. .,~,~
~ . .~;

D4~

The plants were placed lr an r.cubatiGn cabin at lOC% relative atmospheric humidity ar.d at about 20C.
Evaluation was carried out 3 da~Js after the inoculation.
In this test, for example, a clearly superior activity compared to the state of the art was shown by the compounds (l), (8), (16), (30), (31).
Ex~mple B
Phytophthora Test (ton.ato) systemic Solvent: 4.7 parts by weight of acetone Emulsifier: 0.3 parts by weight of alkylaryl polyglycol ether To produce a suitable preparation of active com-pound, l part by weight of active compound was mixed with the stated amounts of solvent and emulsifier, and the conc-entrate was diluted with water to the desired concentratior~.
To test for systemic properties, standard soil containing young plants ready for testing was watered with the preparation of active compound. 3 days after the treatmert, the plants were inoculated with an aqueous spore suspension of Phytophthora infestar.s.
The plants were placed in an incubation cabin at 100% relative atmospheric humidity and at about 2CC.
Evaluation was carried out 3 days after the inocula~ion.
In this test, for example, a clearly superior activity compared to the state of the art was shown by the compounds (1), (8) cr (9).

Le A 21 262 --,~ , ,-~
-~ ,

Claims (31)

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. An N-(alk-1-enyl)-carboxylic acid anilide of the formula (I) in which R1 represents a hydrogen atom or an alkyl radical, R2 represents a hydrogen atom, R3 represents a hydrogen atom or an alkyl, or alkenyl, radical, wherein X1, X2 and X3 independently of one another represent a hydrogen, fluorine, chlorine or bromine atom or a straight chain or branched alkyl radical having 1 to 4 carbon atoms, Y represents a group of the formula Az, -CH2Az or -CH2OR8 wherein R8 represents an alkyl, alkenyl, or alkinyl radical, and Az represents a pyrazol-1-yl, 1,2,4-triazol-1-yl or imidazol-1-yl and when Y represents Az or -CH2Az, a non-phytotoxic acid addition salt or metal salt complex thereof comprising salts of metals of main groups II to IV and of sub-groups I and II and IV to VIII of the periodic table.
2. A compound according to claim 1, in which R1 represents a hydrogen atom or a straight-chain or branched alkyl radical having 1 to 4 carbon atoms;

R2 represents a hydrogen, R3 represents a hydrogen atom, a straight-chain or branched alkyl radical having 1 to 4 carbon atoms, or a straight-chain or branched alkenyl radical having 2 to 6 carbon atoms;
X1, X2, X3, Y and Az are the same as defined in claim 1 and R8 represents an alkyl radical having 1 to 4 carbon atoms or an alkenyl or alkinyl radical each having 2 to 4 carbon atoms.
3. A compound according to claim 2, in which Y represents a 1,2,4-triazol-1-yl, imidazol-1-yl or a group of the formula -CH2Az or -CH2OR8 in which Az and R8 have the same meaning as in claim 2.
4. A compound according to claim 1, in which R1 represents a hydrogen atom or a methyl, ethyl or isopropyl radical, R represents a hydrogen atom, R3 represents a hydrogen atom, a methyl, ethyl, isopropyl, or a straight-chain or branched alkenyl radical having 2 to 4 carbon atoms, or X1 represents a hydrogen atom or a methyl, ethyl, isopropyl, isobutyl, sec.-butyl or tert.-butyl radical or a chlorine or fluorine atom, X2 represents a hydrogen atom, a methyl, ethyl, iso-propyl isobutyl, sec.-butyl or tert.-butyl radical or a chlorine or fluorine atom, Y represents 1,2,4-triazol-1-yl or imidazol-1-yl radical, or a group of the formula -CH2Az or -CH2OR8 in which R8 represents a methyl, ethyl, allyl, propyl, propargyl radical, and Az has the same meaning as in claim 1.
5. N-Methoxyacetyl-N-vinyl-2,6-dimethylaniline of the formula
6. N-Methoxyacetyl-N-(1-methylvinyl)-2,6-dimethylaniline of the formula
7. N-(Imidazol-1-yl-acetyl)-N-vinyl-2,6-dimethylaniline of the formula
8. N~ Methylvinyl)-N (1,2,4-triazol-1-yl--acetyl)-2,6-dimethylaniline of the formula ~IMAGE~
9. N-(1,2,4-Triazol-l-yl-acetyl)-N-vinyl-2,6-dimethyl-aniline of the formula ~IMAGE~
10. N-(l-Methylvinyl)-N-(1,2,4-triazol-1-yl-carbonyl)-2,6-dimethyl aniline of the formula ~IMAGE~
11. N-Propargyloxyacetyl-N-vinyl-2,6-di.methylaniline of the formula ~IMAGE~
12. A compound according to claim 1 wherein Xl and x2 represent a chlorine atom or methyl group, X3 represents hydrogen, Rl is methyl, R2 is hydrogen, R3 is -C(CH3)=CH2 and y is imidazol-l-yl .
13. A compound according to claim 12 wherein Xl is in the 2-position and x2 is in the 6-position on the phenyl ring~
14. N-(Imidazol-l-yl-carbonyl)-N-(Z-methyl-pent-1,3,-dien-4-yl)-2-chloro-2-methylaniline of the formula ~IMAGE~
15. N-(Imidazo~ yl-carbonyl)-N(2-methyl-pent-l/3r-dien-4 yl)-2,6-dimethylaniline of the formula ~IMAGE~

~7
16. A process for the production of a compound according to claim 1, wherein (a) an azine of the general formula (II) in which R1, X1, X2 and X3 have the same meanings as in claim 1 and R4 represents a hydrogen atom or an alkyl, alkoxy, alkoxyalkyl, hydroxyalkyl or benzyl radical, and R5 represents a hydrogen atom or an alkyl, alkenyl, alkoxy, alkoxyalkyl, alkylcarbonyl, alkylcarbonylalkyl, alkoxy-carbonyl or alkoxycarbonylalkyl radical, or R4 and R5 together represent the radical of the general formula wherein R6 represents a hydrogen atom or an alkyl radical. and R7 represents an alkyl or phenyl radical, is reacted with an acid derivative of the general formula Hal-CO-Y (III) in which Hal represents a chlorine or bromine atom and Y has the same meaning as in claim 1, and the resulting acetanilide of the general formula (IV) in which R1, X1, X2, X3 and Y have the same meanings as in claim 1, Hal represents a chlorine or bromine atom and R4 and R5 have the meanings given above, is subjected, without being isolated beforehand, to a process for the elimination of hydrogen halide, or (b) a carbamic acid-chloride of the general formula (V) in which R1, R2, R3, X1, X2 and X3 have the same meanings as in claim 1, is reacted with a compound of the general formula B - Y' (VI) in which Y' represents a grouping of the general formula Az wherein Az has the same meanings as in claim 1, and B represents a hydrogen atom or an alkali metal, or (c) a chloroacetamide of the general formula (VII) in which R1, R2, R3, X1, X2 and X3 have the same meanings as in claim 1, is reacted with a compound of the general formula B - Y '' (VIII) in which B has the same meaning as in reaction variant (b), Y'' represents Az or a grouping of the general formula wherein Az and R8 have the same meanings as in claim 1, or (d) a hydroxyacetanilide of the general formula (IX) in which R1, R2, R3, X1, X2 and X3 have the same meanings as in claim 1, is reacted with a halide, of the general formula Hal - Y ''' (X) in which Y''' represents R8, wherein R8 has the same meaning as in claim 1, and Hal represents a chlorine or bromine atom when Y in the product of reaction variant (a), (b) or (c) represents Az or -CH2Az, a suitable acid or metal salt is added, when required, onto the said product.
17. A method of combating fungi comprising applying to the fungi, or to a habitat thereof, a fungicidally effective amount of .

a compound according to claim 1.
18. A method according to claim 17 wherein the compound is applied in the form of a composition containing said compound as active ingredient in admixture with a suitable diluent or carrier.
19. A method according to claim 18, wherein a composition is used containing from 1 to 0.0001% of the active compound, by weight.
20. A method according to claim 18 wherein a composition is used containing from 0.5 to 0.001% of the active compound, by weight.
21. A method according to claim 17, 18 or 20 wherein said compound is applied to soil in an amount of 0.00001 to 0.1 per-cent by weight.
22. A method according to claim 17, 18 or 20 wherein said compound is applied to soil in an amount of 0.0001 to 0.02 per-cent by weight.
23. A method according to claim 17, 18 or 20 wherein said compound is applied to seed in an amount of 0.001 to 50 g per kg of seed.
24. A method according to claim 17, 18 or 20 wherein said compound is applied to seed in an amount of 0.01 to 10 g per kg of seed.
25. The method according to claim 17, 18 or 20 wherein such compound is N-methoxyacetyl-N-vinyl-2,6-dimethylaniline.
26. The method according to claim 17, 18 or 20 wherein such compound is N-methoxyacetyl-N-(1-methylvinyl)-2,6-dimethylaniline.
27. The method according to claim 17, 18 or 20 wherein such compound is N-(imidazol-1-yl-acetyl)-N-vinyl-2,6-dimethylaniline.
28. The method according to claim 17, 18 or 20 wherein such compound is N-(1-methylvinyl)-N-(1,2,4-triazol-1-yl-acetyl)-2,6-dimethylaniline.
29. The method according to claim 17, 18 or 20 wherein such compound is N-(1,2,4-triazol-1-yl-acetyl)-N-vinyl-2,6-dimethyl-aniline.
30. The method according to claim 17 or 20 wherein the com-pound is a compound of claim 12.
31. The method according to claim 17 or 20 wherein the compound is a compound of claim 13.
CA000411676A 1981-09-18 1982-09-17 N-(alk-1-enyl)-carboxylic acid anilides, processes for their preparation and their use as fungicides Expired CA1194488A (en)

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DE (2) DE3137299A1 (en)
DK (1) DK416682A (en)
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DE3235050A1 (en) * 1982-09-22 1984-03-22 Bayer Ag, 5090 Leverkusen FUNGICIDAL AGENT
CN115141115A (en) * 2021-03-30 2022-10-04 成都倍特药业股份有限公司 Lidocaine hydrochloride impurity and preparation method and detection method thereof

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BG28977A3 (en) * 1978-02-02 1980-08-15 Montedison Spa Fungicide means and method for fungus fighting
DE2910976A1 (en) * 1979-03-21 1980-10-02 Bayer Ag SUBSTITUTED N-ALLYL ACETANILIDES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS FUNGICIDES
DE2916692A1 (en) * 1979-04-25 1980-11-06 Bayer Ag N-ALLENYL ACETANILIDES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS FUNGICIDES
DE3012623A1 (en) * 1980-04-01 1981-10-08 Bayer Ag, 5090 Leverkusen N-ALLENYL HALOGEN ACETANILIDES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS GROWTH REGULATORS AND HERBICIDES

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DE3262337D1 (en) 1985-03-28
ATE11769T1 (en) 1985-02-15
IL66803A0 (en) 1982-12-31
JPS5862146A (en) 1983-04-13
EP0075167A3 (en) 1983-06-01
EP0075167B1 (en) 1985-02-13
ZA826837B (en) 1983-08-31
BR8205477A (en) 1983-08-23
DE3137299A1 (en) 1983-04-14
DK416682A (en) 1983-03-19
EP0075167A2 (en) 1983-03-30

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