EP0820457A1 - Derives benzimidazole - Google Patents

Derives benzimidazole

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Publication number
EP0820457A1
EP0820457A1 EP96909163A EP96909163A EP0820457A1 EP 0820457 A1 EP0820457 A1 EP 0820457A1 EP 96909163 A EP96909163 A EP 96909163A EP 96909163 A EP96909163 A EP 96909163A EP 0820457 A1 EP0820457 A1 EP 0820457A1
Authority
EP
European Patent Office
Prior art keywords
carbon atoms
atoms
alkyl
chain
different halogen
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP96909163A
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German (de)
English (en)
Inventor
Lutz Assmann
Albrecht Marhold
Klaus Stenzel
Martin Kugler
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Bayer AG
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Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP0820457A1 publication Critical patent/EP0820457A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/056—Ortho-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A01N43/52—1,3-Diazoles; Hydrogenated 1,3-diazoles condensed with carbocyclic rings, e.g. benzimidazoles
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/22—Anxiolytics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems

Definitions

  • the present invention relates to new benzimidazole derivatives, a process for their preparation and their use as microbicides in crop protection and in material protection.
  • X 1 , X 2 , X 3 and X 4 independently of one another for hydrogen, halogen, cyano,
  • R 3 and R 4 independently of one another are hydrogen, alkyl, haloalkyl, alkoxyalkyl, alkylcarbonyl, optionally substituted aryl, optionally substituted arylcarbonyl, optionally substituted arylsulfonyl, optionally substituted arylamino carbonyl or optionally substituted arylmethylsulfonyl or
  • R 3 and R 4 together with the nitrogen atom to which they are attached represent an optionally substituted alkyl heterocyclic ring which also contains an oxygen atom or an alkylimino
  • Group can contain
  • Q represents a direct bond or a carbonyl group
  • R 5 represents optionally substituted aryl or optionally substituted heterocyclyl and Z represents a direct bond, CH 2 , O, S, SO, SO 2 , CO or one
  • Azo group stands for -CO-O-, where the oxygen atom is connected to the aryl or heterocyclyl radical, or stands for -SO 2 -O-, where the sulfur atom with the aryl or heterocyclyl radical is connected, or stands for -S-CH 2 -SO 2 -, where the sulfur atom of the thio group is connected to the aryl or heterocyclyl radical, or
  • X and X together represent an optionally substituted alkylene chain with 3 or 4 links, in which one or two (non-adjacent) carbon atoms can be replaced by oxygen atoms,
  • R 6 represents alkyl, haloalkyl or benzyl optionally substituted by halogen and / or haloalkyl
  • R 2 represents optionally substituted heterocyclyl
  • Y for a direct bond, for -CH 2 -, -CH 2 -CH 2 -, -CO-, -SO 2 -, -CO-O- or
  • X 1 , X 2 , X 3 and X 4 have the meanings given above, with halides of the formula
  • R 2 and Y have the meanings given above and
  • Hal represents chlorine or bromine, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, and if appropriate the benzimidazoles of the formula formed in which
  • R 2 , Y, X 1 , X 2 , X 3 and X 4 have the meanings given above, either a) with hydrogen sulfide in the presence of an acid binder and in
  • the substances according to the invention show a better fungicidal activity than 2-cyano-1-dimethylaminosulfonyl-6,6,7,7-tetrafluoro- [1,4] -dioxino [2,3-f] benzimidazole and 2-cyano-6, 6-difluoro-1-dimethylaminosulfonyl [1,3] -dioxolo [4,5-f] benzimidazole, which are constitutionally similar, previously known active ingredients with the same direction of action.
  • X 1 , X 2 , X 3 and X 4 independently of one another preferably represent hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, straight-chain or branched
  • R 3 and R 4 independently of one another preferably represent hydrogen, straight-chain or branched alkyl having 1 to 6 carbon atoms, straight-chain or branched haloalkyl having 1 to 6 carbon atoms and
  • Aryl radicals can be monosubstituted to trisubstituted, identical or different, by halogen, cyano, nitro, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, haloalkoxy with 1 to 4
  • R 3 and R 4 also together with the nitrogen atom to which they are attached preferably represent a heterocyclic radical which is optionally monosubstituted to trisubstituted by alkyl having 1 to 4 carbon atoms
  • C 1 -C 4 alkylimino group can contain.
  • Q also preferably represents a direct bond or a carbonyl
  • R 5 preferably represents aryl having 6 to 10 carbon atoms, where each of these radicals can be substituted once to three times, identically or differently, by halogen, cyano, nitro, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 up to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, haloalkoxy with 1 to 4
  • R 5 preferably represents a saturated or unsaturated heterocyclyl-
  • Z also preferably represents a direct bond and also CH 2 , O, S, SO,
  • X and X also preferably together represent an optionally one to six times by halogen, alkyl having 1 to 4 carbon atoms and / or haloalkyl having 1 to 4 carbon atoms and 1 to 9
  • Halogen atoms substituted alkylene chain with 3 or 4 links in which one or two (non-adjacent) carbon atoms can be replaced by oxygen atoms.
  • R 1 also preferably represents cyano or the groupings
  • R 6 preferably represents straight-chain or branched alkyl having 1 to 4 carbon atoms, straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms or optionally single to triple, identical or different by halogen and / or haloalkyl benzyl substituted with 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms.
  • R 2 preferably represents a saturated or unsaturated, optionally benzanellated heterocyclyl radical with 5 or 6 ring members and 1 to 3
  • Heteroatoms such as nitrogen, oxygen and / or sulfur, it being possible for these radicals to be monosubstituted to triple, identical or differently substituted by halogen, cyano, nitro, hydroxyl, amino, formyl, carboxy, carbamoyl, thiocarbamoyl, alkyl having 1 to 4 carbon atoms , Alkoxy with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, haloalkoxy with 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, alkoxycarbonyl with 1 to 4 carbon atoms in the alkoxy part, cycloalkyl with 3 to 6 carbon atoms, haloalkylsulfinyl with 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, haloalkylsulfonyl with 1 to 4 carbon atoms and 1 to
  • Y also preferably represents a direct bond, CH 2 , CH 2 -CH 2 , CO, SO 2 , -CO-O- or -SO-O-, in the case of the latter two groups the carbon atom or the Sulfur atom is connected to the nitrogen atom of the imidazole ring.
  • X 1 , X 2 , X 3 and X 4 independently of one another are particularly preferably
  • alkylcarbonyl with 1 to 4 carbon atoms in the straight-chain or branched alkyl part alkoxycarbonyl with 1 to 4 carbon atoms in the straight-chain or branched alkoxy part
  • cycloalkylcarbonyl with 3 to 6 carbon atoms in the cycloalkyl part cycloalkoxycarbonyl with 3 to 6 carbon atoms in the cycloalkyl part, for
  • R 3 and R 4 independently of one another particularly preferably represent hydrogen, straight-chain or branched alkyl having 1 to 4 carbon atoms, haloalkyl having 1 or 2 carbon atoms and 1 to 5 fluorine, chlorine and / or bromine atoms, straight-chain or branched alkoxyalkyl having 1 up to 3 carbon atoms in the alkoxy part and 1 to 3 carbon atoms in the alkyl part, alkylcarbonyl with 1 to 4 carbon atoms in the straight-chain or branched alkyl part, phenyl, phenylcarbonyl, phenylsulfonyl, phenylaminocarbonyl or phenylmethylsulfonyl, each of the above Phenyl radicals mentioned can be monosubstituted to trisubstituted, identical or different, by fluorine, chlorine, bromine, cyano, nitro, alkyl having 1 or 2 carbon atoms, alkoxy having 1 or 2 carbon atom
  • R 3 and R 4 also together with the nitrogen atom to which they are attached are particularly preferred for a saturated heterocyclic ring with 5 or 6 ring members which is optionally mono- to trisubstituted by methyl and / or ethyl, one carbon atom of
  • Ringes can be replaced by oxygen or methylimino.
  • Q also particularly preferably represents a direct bond or a carbonyl group.
  • R 5 particularly preferably represents phenyl which can be monosubstituted to trisubstituted, identical or different, by fluorine, chlorine, bromine, cyano, nitro, alkyl having 1 or 2 carbon atoms, alkoxy having 1 or 2 carbon atoms, alkylthio having 1 or 2 Carbon atoms, haloalkyl with 1 or 2 carbon atoms and 1 to 5 fluorine, chlorine and / or bromine atoms, haloalkoxy with 1 or 2 carbon atoms and 1 to 5
  • R 3 particularly preferably represents a saturated or unsaturated heterocyclyl radical having 5 or 6 ring members and 1 to 3 heteroatoms, such as nitrogen, oxygen and / or sulfur, it being possible for these radicals to be monosubstituted to trisubstituted, identical or different, by fluorine, chlorine , Bromine, alkyl with 1
  • Z also particularly preferably represents a direct bond and also CH 2 , O,
  • Radical is connected, or for -S-CH 2 -SO 2 , the sulfur atom of the thio group being connected to the phenyl or heterocyclyl radical.
  • X 2 and X 3 together also particularly preferably represent an alkylene chain with 3 or 4 links which is optionally monosubstituted to 6-fold substituted by fluorine, chlorine, methyl and / or trifluoromethyl, in which one or two (non-adjacent) carbon atoms can be replaced by oxygen.
  • R 1 also particularly preferably represents cyano or the groupings
  • R 6 particularly preferably represents straight-chain or branched alkyl having 1 to 4 carbon atoms, straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 5 fluorine, chlorine and / or bromine atoms, or optionally single or double, similar or differently substituted by fluorine, chlorine and / or trifluoromethyl benzyl.
  • R 2 particularly preferably represents a saturated or unsaturated, optionally benzanellated heterocyclyl radical having 5 or 6 ring members and 1 to 3 heteroatoms, such as nitrogen, oxygen and / or sulfur, where these radicals can be substituted by up to three, identical or different Fluorine, chlorine, bromine, cyano, nitro, hydroxy, amino, formyl, carboxy, carbamoyl, thiocarbamoyl, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, haloalkyl with 1 or 2 carbon atoms and 1 to 5 fluorine, Chlorine and / or
  • Y also particularly preferably stands for a direct bond, for CH 2 , CH 2 -CH 2 , CO, SO 2 , -CO-O- or -SO-O-, where in the case of the latter two groups the carbon atom or the Sulfur atom is connected to the nitrogen atom of the imidazole ring.
  • X 1 , X 2 , X 3 and X 4 independently of one another very particularly preferably represent hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfonyl, methylsulfonyl, ethylsulfonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluoromethylthio, trifluoromethylmethyl , Trifluoromethylsulfonyl, acetyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, cyclopropyl,
  • R 3 and R 4 also together with the nitrogen atom to which they are attached very particularly preferably represent pyrrolidinyl, piperidinyl, morpholinyl or 4-methyl-piperazinyl.
  • Q also very particularly preferably stands for a direct bond or for a
  • R 5 very particularly preferably represents phenyl, which can be substituted once to three times, in the same way or differently, by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluoromethylthio, trifluoromluoromethylthio or trifluoromethylsulfonyl, or R 5 very particularly preferably represents pyrrolyl, furyl, thienyl, pyrazolyl,
  • Trifluoromethoxy also very particularly preferably stands for a direct bond and for
  • Radical is connected, or for -S-CH 2 -SO 2 -, the sulfur atom of the thio group being connected to the phenyl or heterocylyl radical.
  • X 2 and X 3 together also very particularly preferably stand for the groupings -O-CF 2 -O-, -O-CF 2 -CHF-O-, -O-CHF-CHF-O-,
  • R 1 also very particularly preferably represents cyano or the groupings
  • R 6 very particularly preferably represents methyl, ethyl, isopropyl, trichloromethyl, trifluoromethyl or benzyl.
  • R 2 very particularly preferably represents pyrrolyl, furyl, thienyl, pyrazolyl,
  • radicals can be substituted once to three times, in the same way or differently, by fluorine, chlorine, bromine, cyano, nitro, amino, Hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n - or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluoromethylthio, trifluoromethylthio, trifluoro-methylsulfinyl, or trifluoromethylsulfonyl,
  • Y also very particularly preferably represents a direct bond, CH 2 ,
  • Preferred compounds according to the invention are also addition products of acids and those benzimidazole derivatives of the formula (I) in which R 1 , R 2 , X 1 , X 2 , X 3 , X 4 and Y have those meanings which are preferred for these radicals were called.
  • the acids which can be added preferably include hydrohalic acids, such as, for example, hydrochloric acid and hydrobromic acid, in particular hydrochloric acid, furthermore phosphoric acid, nitric acid, mono- and bifunctional carboxylic acids and hydroxycarboxylic acids, such as, for example, acetic acid, maleic acid, succinic acid, fumaric acid, tartaric acid , Citric acid, salicylic acid, sorbic acid and lactic acid, as well as sulfonic acids such as p-toluenesulfonic acid, 1,5-naphthalenedisulfonic acid and also saccharin and thiosaccharin.
  • hydrohalic acids such as, for example, hydrochloric acid and hydrobromic acid, in particular hydrochloric acid, furthermore phosphoric acid, nitric acid, mono- and bifunctional carboxylic acids and hydroxycarboxylic acids, such as, for example, acetic acid, maleic acid, succinic acid, fumaric
  • preferred compounds according to the invention are addition products from salts of metals of the II. To IV. Main group and of I. and II. And IV. To VIII. Subgroup of the periodic table of the elements and those benzimidazole derivatives of the formula (I), in where R 1 , R 2 , X 1 , X 2 , X 3 , X 4 and Y have the meanings which have been mentioned as preferred for these radicals. Salts of copper, zinc, manganese, magnesium, tin, iron and nickel are particularly preferred. Anions of these salts are those which are derived from acids which lead to physiologically tolerable addition products. Particularly preferred acids in this connection are the hydrohalic acids, such as, for example, the hydrochloric acid and the hydrobromic acid, and also phosphoric acid, nitric acid and sulfuric acid.
  • hydrohalic acids such as, for example, the hydrochloric acid and the hydrobromic acid, and also phosphoric acid, nitric acid and sulfuric acid.
  • Formula (II) provides a general definition of the cyano-benzimidazoles required as starting materials for carrying out the first stage of the process according to the invention.
  • X 1 , X 2 , X 3 and X 4 have those meanings which have already been mentioned for these radicals in connection with the description of the substances of the formula (I) according to the invention.
  • the cyano-benzimidazoles of the formula (II) are known or can be prepared by methods known in principle (cf. DE-A 4 139 950, FR-A 2 572 412, EP-A 0 181 826, EP-A 0 517 476, EP-A 0 549 943 and EP-A 0 487 286).
  • the also in the implementation of the first stage of the invention are known or can be prepared by methods known in principle (cf. DE-A 4 139 950, FR-A 2 572 412, EP-A 0 181 826, EP-A 0 517 476, EP-A 0 549 943 and EP-A 0 487 286).
  • the also in the implementation of the first stage of the invention are known or can be prepared by methods known in principle (cf. DE-A 4 139 950, FR-A 2 572 412, EP-A 0 181 826, EP-A 0 517 476, EP-A 0 549
  • the halides required as starting materials for the process are generally defined by the formula (III).
  • R 2 and Y have those meanings which have already been mentioned for these radicals in connection with the description of the substances of the formula (I) according to the invention.
  • Shark stands for chlorine or bromine.
  • the halides of the formula (III) are known or can be prepared according to known ones
  • Suitable diluents for carrying out the first stage of the process according to the invention are all customary inert, organic solvents.
  • Aliphatic, cycloaliphatic and aromatic, optionally halogenated hydrocarbons such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform or carbon tetrachloride, can preferably be used; also ethers, such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether, furthermore ketones, such as acetone or butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or benzonitrile, or
  • Esters such as methyl acetate or ethyl acetate.
  • the process is preferably carried out in the presence of an acid binder.
  • All conventional inorganic or organic bases are suitable as such.
  • Alkaline earth or alkali metal hydroxides such as sodium hydroxide, calcium hydroxide, potassium hydroxide, or also ammonium hydroxide, alkali metal carbonates, such as sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate, alkali metal or alkaline earth metal acetates, such as sodium acetate, potassium acetate, amine acetate, and tertiary, are preferably usable.
  • DBU diazabicyclooctane
  • DBN diazabicyclonones
  • DBU diazabicycloundecene
  • reaction temperatures can be varied within a substantial range when carrying out the first stage of the process according to the invention. In general, temperatures between 0 and 150 ° C, preferably at temperatures between 20 and 120 ° C.
  • the process according to the invention is usually carried out under normal pressure both in the first and in the second stage. However, it is also possible to work under increased or reduced pressure.
  • 1.0 to 2.0 mol, preferably 1.0 to 1.3 mol, of halide of the formula (III.) are generally employed per mol of cyano-benzimidazole of the formula (II) in a diluent ) and optionally 1.0 to 2.0 mol, preferably 1.0 to 1.3 mol of acid binder.
  • the reaction, working up and isolation of the reaction products is carried out according to known processes (cf. also the preparation examples).
  • preferred acid binders are preferably tertiary amines, such as triethylamine.
  • Suitable diluents for carrying out the second stage of the process according to the invention are all inert, polar organic
  • Amides such as dimethyl formamide, also ethers, such as diethyl ether or tetrahydrofuran and aromatic amines, such as pyridine.
  • reaction temperatures can also be varied within a substantial range when carrying out the second stage (variant a) of the process according to the invention. In general, temperatures between -20 ° C and + 150 ° C, preferably between -10 ° C and + 80 ° C.
  • Formula (IV) provides a general definition of the sulfur compounds required as reaction components when carrying out the second stage (variant b) of the process according to the invention.
  • R 6 has the meanings which have already been mentioned for this radical in connection with the description of the substances of the formula (I) according to the invention.
  • alkali metal carbonates such as sodium carbonate or potassium carbonate
  • acid binders When carrying out the second stage (variant b) of the process according to the invention, alkali metal carbonates, such as sodium carbonate or potassium carbonate, are preferred as acid binders.
  • Suitable diluents for carrying out the second stage (variant b) of the process according to the invention are all customary polar, aprotic ones
  • Nitriles such as acetonitrile, can preferably be used.
  • reaction temperatures can also be varied within a substantial range when carrying out the second stage (variant b) of the process according to the invention.
  • temperatures between -20 ° C and + 150 ° C, preferably between -10 ° C and + 80 ° C.
  • the acid addition salts of the compounds of formula (I) can be easily prepared by conventional salt formation methods, e.g. by dissolving a compound of formula (I) in a suitable inert solvent and adding the acid, e.g. Hydrochloric acid can be obtained and in a known manner, e.g. by filtration, isolated and, if necessary, cleaned by washing with an inert organic solvent.
  • a suitable inert solvent e.g. Hydrochloric acid
  • metal salt complexes of the compounds of formula (I) preference is given to those salts of metals which have already been mentioned as preferred metal salts in connection with the description of the metal salt complexes according to the invention.
  • the metal salt complexes of the compounds of formula (I) can be obtained in a simple manner by conventional methods, e.g. by dissolving the metal salt in alcohol, e.g. Ethanol and adding to compounds of formula (I).
  • Metal salt complexes can be prepared in a known manner, e.g. by filtering, isolating and, if necessary, cleaning by recrystallization.
  • the active compounds according to the invention have a strong microbicidal action and can be used to protect against undesirable microorganisms, such as fungi and bacteria, in crop protection and in the material.
  • Undesirable microorganisms include fungi such as Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes and further bacteria such as Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomyceae.
  • Xanthomonas species such as Xanthomonas oryzae
  • Pseudomonas species such as Pseudomonas lachrymans
  • Erwinia species such as Erwinia amylovora
  • Pythium species such as Pythium ultimum
  • Phytophthora species such as Phytophthora infestans
  • Pseudoperonospora species such as Pseudoperonospora humuli or Pseudoperonospora cubensis;
  • Plasmopara species such as Plasmopara viticola
  • Peronospora species such as Peronospora pisi or P. brassicae;
  • Erysiphe species such as Erysiphe graminis
  • Sphaerotheca species such as Sphaerotheca fuliginea
  • Podosphaera species such as Podosphaera leucotricha
  • Venturia species such as Venturia inaequalis
  • Pyrenophora species such as Pyrenophora teres or P. graminea;
  • Drechslera (Coni form: Drechslera, Syn: Helminthosporium);
  • Cochliobolus species such as Cochliobolus sativus
  • Drechslera (Conidial form: Drechslera, Syn: Helminthosporium);
  • Uromyces species such as Uromyces appendiculatus
  • Puccinia species such as Puccinia recondita
  • Tilletia species such as Tilletia caries
  • Ustilago species such as Ustilago nuda or Ustilago avenae
  • Pellicularia species such as Pellicularia sasakii
  • Pyricularia species such as Pyricularia oryzae
  • Fusarium species such as Fusarium culmorum
  • Botrytis species such as Botrytis cinerea
  • Septoria species such as Septoria nodorum
  • Leptosphaeria species such as Leptosphaeria nodorum
  • Cercospora species such as Cercospora canescens
  • Alternaria species such as Alternaria brassicae
  • Pseudocercosporella species such as Pseudocercosporella herpotrichoides.
  • the fact that the active compounds are well tolerated by plants in the concentrations required to combat plant diseases allows treatment of above-ground parts of plants, of propagation stock and seeds and of the soil.
  • the active compounds according to the invention can be used with particularly good results in combating diseases in fruit and vegetable growing, for example against
  • Venturia species or for combating cereal diseases such as, for example, Erysiphe, Cochliobolus, Pyrenophora or Septoria species, or for combating rice diseases, such as, for example, against the pathogen causing rice stain disease (Pyricularia oryzae).
  • the substances according to the invention can be used to protect technical materials against attack and destruction by undesired microorganisms.
  • technical materials are to be understood as non-living materials that have been prepared for use in technology.
  • technical materials which are to be protected against microbial change or destruction by active substances according to the invention can be adhesives, glues, paper and cardboard, textiles, leather, wood, paints and plastic articles, cooling lubricants and other materials which can be attacked or decomposed by microorganisms .
  • parts of production plants for example cooling water circuits, are also mentioned which can be impaired by the multiplication of microorganisms.
  • technical materials are preferably adhesives, glues, papers and cartons, leather, wood, paints, cooling lubricants and heat transfer liquids, particularly preferably wood.
  • Bacteria, fungi, yeasts, algae and mucilaginous organisms may be mentioned as microorganisms which can cause degradation or a change in the technical materials.
  • the active compounds according to the invention preferably act against fungi, in particular mold, wood-discoloring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae.
  • microorganisms of the following genera may be mentioned: Alternaria, such as Alternaria tenuis,
  • Aspergillus such as Aspergillus niger
  • Chaetomium like Chaetomium globosum
  • Coniophora such as Coniophora puetana
  • Lentinus such as Lentinus tigrinus
  • Penicillium such as Penicillium glaucum
  • Polyporus such as Polyporus versicolor
  • Aureobasidium such as Aureobasidium pullulans
  • Sclerophoma such as Sclerophoma pityophila
  • Trichoderma like Trichoderma viride
  • Escherichia such as Escherichia coli
  • Pseudomonas such as Pseudomonas aeruginosa
  • Staphylococcus such as Staphylococcus aureus.
  • the active compounds according to the invention are suitable for controlling animal pests, preferably arthropods and nematodes, in particular insects and arachnids, which occur in agriculture, in forests, in the protection of stored goods and materials and in the hygiene sector. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the cyanobenzimidazoles of the formula (II) are also notable for their fungicidal activity.
  • the active compounds can be converted into customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for
  • formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or
  • organic solvents such as Alcohols can be used as auxiliary solvents.
  • the following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, alcohols, how
  • liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and under normal pressure, e.g. Aerosol propellants, such as halogenated hydrocarbons such as butane, propane, nitrogen and carbon dioxide; as solid carriers are possible: e.g.
  • natural rock meals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock meals, such as highly disperse silica, aluminum oxide and silicates; as solid carriers for granules are possible: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; come in as emulsifying and / or foaming agents
  • non-ionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates;
  • Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide,
  • Ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc are used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can be used in the formulations in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order, for example, to to broaden the spectrum of effects or to prevent the development of resistance.
  • Fenpropimorph Fentinacetate, Fentinhydroxyd, Ferbam, Ferimzone, Fluazinam, Fludioxonil, Fluoromide, Fluquinconazole, Flusilazole, Flusulfamide, Flutolanil, Flutriafol, Folpet, Fosetyl-Aluminum, Fthalide, Fuberidazol, Furaloxyl, Furmax
  • Imazalil Imibenconazol, Iminoctadin, Iprobefos (IBP), Iprodione, Isoprothiolan, Kasugamycin
  • copper preparations such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine copper and Bordeaux mixture,
  • Mancopper Mancozeb, Maneb, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfuroxam, Metiram, Metsulfovax, Myclobutanil,
  • Tebuconazole Tecloftalam, Tecnazen, Tetraconazole, Thiabendazole, Thicyofen, Thiophanat-methyl, Thiram, Tolclophos-methyl, Tolylfluanid, Triadimefon, Triadimenol, Triazoxid, Trichlamid, Tricyclazol, Tridemorph, Trifluminol, Trifluminol
  • Bactericides bronopol, dichlorophene, nitrapyrin, nickel-dimethyldithiocarbamate, kasugamycin, octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulfate and other copper preparations.
  • Cadusafos Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, CGA 157 419, CGA 184699, Chloethocarb, Chlorethoxyfos, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chlorpyrifos, Chlorpyrifos M, Cis-Resmethrin,
  • Fenamiphos Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenothxinfox, Fufionophon, Fufionophon, Fufionophon, Fufionophon, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fu
  • Imidacloprid Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivemectin, Lambda-cyhalothrin, Lufenuron,
  • Parathion A Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenofos, Promecarb, Propaphos, Propoxur, Prothiofos, Prothoat, Pymetrozin, Pyrachlophhion, Pyrachlophhion, Pyrachlophhion, Pyrachlophhion, Pyrachlophhion, Pyrachlophion, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophion Pyridaben, Pyrimidifen, Pyriproxifen, Quinalphos, RH 5992,
  • Tebufenozid Tebufenpyrad
  • Tebupirimiphos Teflubenzuron
  • Tefluthrin Temephos
  • Terbam Terbufos
  • Tetrachlorvinphos Thiafenox, Thiodicarb, Thiofanox, Thiomethon, Thionazin, Thuringiensin, Tralathenethrin, Triarathenethrin
  • Triazophos triazuron, trichlorfon, triflumuron, trimethacarb,
  • the active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules. They are used in the usual way, e.g. by pouring, spraying, atomizing, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients by the ultra-low-volume process or to inject the active ingredient preparation or the active ingredient into the soil itself. The seeds of the plants can also be treated.
  • the active compound concentrations in the use forms can be varied within a substantial range: they are generally between 1 and 0.0001% by weight, preferably between 0.5 and
  • amounts of active ingredient of 0.001 to 50 g per kilogram of seed, preferably 0.01 to 10 g, are generally required.
  • active ingredient concentrations of 0.00001 to 0.1% by weight, preferably 0.0001 to 0.02% by weight, are required at the site of action.
  • the agents used to protect industrial materials generally contain the active ingredients in an amount of 1 to 95%, preferably 10 to
  • the application concentrations of the active compounds according to the invention depend on the type and the occurrence of the microorganisms to be controlled and on the composition of the material to be protected. The optimal amount can be determined by test series. In general, the application concentrations are in the range from 0.001 to 5% by weight, preferably from 0.05 to 1.0% by weight, based on the material to be protected.
  • Sulfenamides such as dichlorfluanid (Euparen), tolyfluanid (Methyl euparen), folpet, fluorfolpet;
  • Benzimidazoles such as Carbendazim (MBC), Benomyl, Fuberidazole, Thiabendazole or their salts;
  • Thiocyanates such as thiocyanatomethylthiobenzothiazole (TCMTB), methylene bisthiocyanate (MBT); quaternary ammonium compounds such as benzyldimethyltetradecylammonium chloride, benzyldimethyldodecylammonium chloride, dodecyldimethylammonium chloride;
  • Morpholine derivatives such as C 11 -C 14 -4-alkyl-2,6-dimethyl-morpholine homologue (tridemorph), (+) - cis-4- [tert-butylphenyl) -2-methylpropyl] -2,6-dimethylmorpholine (fenpropimorph ), Falimorph; Phenols such as o-phenylphenol, tribromophenol, tetrachlorophenol, pentachlorophenol, 3-methyl-4-chlorophenol, dichlorophen, chlorophen or their salts;
  • Azoles such as triadimefon, triadimenol, bitertanol, tebuconazole, propiconazole, azaconazole, hexaconazole, prochloraz, cyproconazole, 1- (2-chlorophenyl) -2- (1-chlorocyclopropyl) -3- (1,2,4-triazol-1-yl ) -propan-2-ol or 1- (2-chlorophenyl) -2-
  • Iodopropargyl derivatives such as iodopropargyl butyl carbamate (IPBC), chlorophenyl formal, phenyl carbamate, hexyl carbamate, cyclohexyl carbamate, iodopropargy loxy ethyl phenyl carbamate; Iodine derivatives such as diiodomethyl-p-arylsulfones e.g. Diiodomethyl p-tolyl sulfone;
  • IPBC iodopropargyl butyl carbamate
  • Iodine derivatives such as diiodomethyl-p-arylsulfones e.g. Diiodomethyl p-tolyl sulfone;
  • Bromine derivatives such as bromopol
  • Isothiazolines such as N-methylisothiazolin-3-one, 5-chloro-N-methylisothiazolin-3-one, 4,5-dichloro-N-octylisothiazolin-3-one, N-octylisothiazolin-3-one (octilinone);
  • Pyridines such as 1-hydroxy-2-pyridinthione (and their Na, Fe, Mn, Zn salts), tetrachloro-4-methylsulfonylpyridine;
  • Metal soaps such as tin, copper, zinc naphthenate, octoate, 2-ethylhexanoate, oleate, phosphate, benzoate, oxides such as TBTO, Cu 2 O, CuO, ZnO;
  • Organic tin compounds such as tributyltin naphtenate and tributyltin oxide; Dialkyldithiocarbamates such as Na and Zn salts of dialkyldithiocarbamates,
  • TMTD Tetramethyl tiuramide disulfide
  • Nitriles such as 2,4,5,6-tetrachloroisophthalonitrile (chlorothalonil) etc.
  • Halogenated microbicides such as Cl-Ac, MCA, tectamer, bromopol, bromidox;
  • Benzothiazoles such as 2-mercaptobenzothiazoles; says Dazomet; Quinolines such as 8-hydroxyquinoline;
  • Formaldehyde-releasing compounds such as benzyl alcohol mono (poly) hemiformal, oxazolidines, hexahydro-s-triazines, N-methylolchloroacetamide;
  • Phosphoric acid esters such as azinphos-ethyl, azinphos-methyl, 1- (4-chlorophenyl) -4- (O-ethyl, S-propyl) phosphoryloxypyrazole (TIA-230), chlorpyrifos, Coumaphos, Demon, Demeton-S-methyl, Diazinon, Dichlorfos, Dimethoate, Ethoprophos, Etrimfos, Fenitrothion, Fention, Heptenophos, Parathion, Parathion-methyl, Phosalone, Phoxim, Pirimiphos-ethyl, Pirimiphos-methyl, Profenofos, Prothiofos, Sulprofos, Triazophos and Trichlorph.
  • chlorpyrifos Coumaphos, Demon, Demeton-S-methyl, Diazinon, Dichlorfos, Dimethoate, Ethoprophos, Etrimfos, Fenitrothion, Fen
  • Carbamates such as aldicarb, bendiocarb, BPMC (2- (l-methylpropyl) phenylmethyl carbamate), butocarboxime, butoxycarboxime, carbaryl, carbofuran, carbosulfane,
  • Cloethocarb Isoprocarb, Methomyl, Oxamyl, Pirimicarb, Promecarb, Propoxur and Thiodicarb.
  • Pyrethroids such as allethrin, alphamethrin, bioresmethrin, byfenthrin (FMC 54800), cycloprothrin, cyfluthrin, decamethrione, cyhalothrin, cypermethrin, deltamethrin, alpha-cyano-3-phenyl-2-methylbenzyl-2,2-dimethyl-3- ( -2-trifluoromethyl vinyl) cyclopropane carboxylate, fenpropathrin, fenfluthrin, fenvalerate, flucythrinate, flumethrin, fluvalinate, permethrin and resmethrin; Nitroimino and nitromethylene compounds such as 1 - [(6-chloro-3-pyridinyl) methyl] -4,5-dihydro-N-nitro-1H-imidazol-2-amine (imidachloprid).
  • Organosilicon compounds preferably dimethyl (phenyl) silylmethyl-3-phenoxybenzyl ether such as dimethyl (4-ethoxyphenyl) silylmethyl-3-phenoxybenzyl ether or dimethyl (phenyl) silylmethyl-2-phenoxy-6-pyridylmethyl ether such as dimethyl ( 9-ethoxyphenyl) silylmethyl-2-phenoxy-6-pyridylmethyl ether or (Phe nyl) [3- (3-phenoxyphenyl) propyl] (dimethyl) silanes such as (4-ethoxyphenyl) - [3 (4-fluoro-3-phenoxyphenyl) propyl] dimethylsilane.
  • the preparation and use of active compounds according to the invention are illustrated by the following examples.
  • Emulsifier 0.3 part by weight of alkylaryl polyglycol ether. To prepare a suitable preparation of active compound, mix
  • Example B the compounds according to Examples 1 to 3 at an active ingredient concentration of 10 ppm in the spray mixture show an efficiency of more than 50%, while the comparison substance (A) has an activity of 43% and the comparison substance (B) has no effect.
  • Example B the comparison substance (A) has an activity of 43% and the comparison substance (B) has no effect.
  • Emulsifier 0.3 part by weight of alkyl aryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • the plants are placed in an incubation cabin with 100% relative humidity and approx. 20 ° C.
  • Evaluation is carried out 3 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
  • Emulsifier 0.3 part by weight of alkyl aryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • young plants are sprayed with the preparation of active compound to runoff. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Plasmopara viticola and then remain in a moist chamber at 20-22 ° C. and 100% relative atmospheric humidity for 1 day. The plants are then placed in a greenhouse at 21 ° C. and 90% humidity for 5 days. The plants are then moistened and placed in a moisture chamber for 1 day.

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Abstract

L'invention concerne de nouveaux dérivés benzimidazole de la formule (I), dans laquelle R2 désigne hétérocyclyle éventuellement substitué et Y désigne une liaison directe, -CH¿2?-, -CH2-CH2-, -CO-, SO2-, -CO-O- ou -SO-O-, dans le cas des deux derniers groupes cités, l'atome de carbone ou l'atome de soufre étant lié à l'atome d'azote du composé cyclique imidazole. L'invention concerne en outre un procédé permettant de préparer ces substances et leur utilisation comme microbicides dans le domaine phytosanitaire et la protection des matériaux.
EP96909163A 1995-04-13 1996-04-01 Derives benzimidazole Withdrawn EP0820457A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19513990 1995-04-13
DE19513990A DE19513990A1 (de) 1995-04-13 1995-04-13 Benzimidazol-Derivate
PCT/EP1996/001435 WO1996032395A1 (fr) 1995-04-13 1996-04-01 Derives benzimidazole

Publications (1)

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EP0820457A1 true EP0820457A1 (fr) 1998-01-28

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US (4) US5925663A (fr)
EP (1) EP0820457A1 (fr)
JP (1) JPH11503725A (fr)
KR (1) KR19980703800A (fr)
AU (1) AU5276596A (fr)
BR (1) BR9604831A (fr)
CZ (1) CZ324597A3 (fr)
DE (1) DE19513990A1 (fr)
HU (1) HUP9801565A3 (fr)
PL (1) PL185393B1 (fr)
RU (1) RU2159242C2 (fr)
SK (1) SK137197A3 (fr)
WO (1) WO1996032395A1 (fr)

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WO1996004270A1 (fr) * 1994-08-04 1996-02-15 Synaptic Pharmaceutical Corporation Nouveaux derives de benzimidazole
DE19517840A1 (de) * 1995-05-16 1996-11-21 Bayer Ag Wirkstoffkombinationen
DE19708688A1 (de) * 1997-03-04 1998-09-10 Bayer Ag Annellierte Azolderivate
US6495583B1 (en) 1997-03-25 2002-12-17 Synaptic Pharmaceutical Corporation Benzimidazole derivatives
KR101647856B1 (ko) * 2008-07-18 2016-08-11 다우 글로벌 테크놀로지스 엘엘씨 살생물 조성물
AR115088A1 (es) 2018-05-15 2020-11-25 Bayer Ag Espirociclohexilpirrolin-2-onas y su uso como herbicidas
WO2019219585A1 (fr) 2018-05-15 2019-11-21 Bayer Aktiengesellschaft Nouvelles 3-(4-alcinyl-6-alcoxy-2-chlorophényl)-3-pyrrolin-2-ones et leur utilisation comme herbicides
CA3100089A1 (fr) 2018-05-15 2019-11-21 Bayer Aktiengesellschaft Pyrrolin-2-ones a substitution 2-bromo-6-alcoxyphenyle et leur utilisation comme herbicides
WO2019228787A1 (fr) 2018-05-29 2019-12-05 Bayer Aktiengesellschaft 2-alkyle-6-alcoxyphényle-pyrroline-2-ones à substitution spéciale et leur utilisation comme herbicides
WO2019228788A1 (fr) 2018-05-29 2019-12-05 Bayer Aktiengesellschaft Pyrorroline-2-ones à substitution 2-bromo-6-alcoxyphényle et leur utilisation comme herbicides

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AU4948093A (en) * 1992-08-25 1994-03-15 Ciba-Geigy Ag Benzimidazole derivatives as microbicides
DE4237557A1 (de) * 1992-11-06 1994-05-11 Bayer Ag Substituierte Benzimidazole
DE4237567A1 (de) * 1992-11-06 1994-05-11 Bayer Ag Schädlingsbekämpfungsmittel

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Title
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US5925663A (en) 1999-07-20
HUP9801565A3 (en) 2001-11-28
SK137197A3 (en) 1998-05-06
KR19980703800A (ko) 1998-12-05
PL185393B1 (pl) 2003-05-30
RU2159242C2 (ru) 2000-11-20
US6080776A (en) 2000-06-27
HUP9801565A2 (hu) 1998-09-28
PL322721A1 (en) 1998-02-16
DE19513990A1 (de) 1996-10-17
US20020026059A1 (en) 2002-02-28
CZ324597A3 (cs) 1998-01-14
BR9604831A (pt) 1999-01-05
US6235765B1 (en) 2001-05-22
AU5276596A (en) 1996-10-30
WO1996032395A1 (fr) 1996-10-17
JPH11503725A (ja) 1999-03-30

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