EP0589932A1 - Sulphonyl formamidrazones, methods of preparing them, agents containing them, and their use against plant pests - Google Patents

Sulphonyl formamidrazones, methods of preparing them, agents containing them, and their use against plant pests

Info

Publication number
EP0589932A1
EP0589932A1 EP92911540A EP92911540A EP0589932A1 EP 0589932 A1 EP0589932 A1 EP 0589932A1 EP 92911540 A EP92911540 A EP 92911540A EP 92911540 A EP92911540 A EP 92911540A EP 0589932 A1 EP0589932 A1 EP 0589932A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
formula
alkoxy
alkenyl
alkynyl
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Withdrawn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
EP92911540A
Other languages
German (de)
French (fr)
Inventor
Hilmar Mildenberger
Frank Zurmühlen
Peter Braun
Burkhard Sachse
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
Hoechst AG
Hoechst Schering Agrevo GmbH
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Hoechst AG, Hoechst Schering Agrevo GmbH filed Critical Hoechst AG
Publication of EP0589932A1 publication Critical patent/EP0589932A1/en
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/40—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • A01N47/42—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
    • C07C381/14—Compounds containing a carbon atom having four bonds to hetero atoms with a double bond to one hetero atom and at least one bond to a sulfur atom further doubly-bound to oxygen atoms

Definitions

  • the present invention relates to sulfonylformamide razones, processes for their preparation, compositions containing them and their use against
  • Plant pests in particular as fungicides.
  • the invention relates to sulfonylformamide zones of the general formula (I) and their tautomers of the general formula (II),
  • R 1 alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, the 5 groups
  • R 2 alkyl, alkenyl, alkynyl, phenyl and benzyl, the 5 groups independently of one another unsubstituted or one or more times by the radicals
  • Halogen, cyano, nitro, mono- and dialkylamino, alkoxy, haloalkyl can be substituted or a radical of the formula -C (O) R 2 ' , -SO 2 R 2' , wherein
  • R 2 ' alkyl, alkenyl, alkynyl, phenyl and benzyl, the 5 groups independently of one another unsubstituted or one or more times by the radicals
  • Halogen, cyano, nitro, mono- and dialkylamino, alkoxy, haloalkyl can be substituted
  • n an integer from 0 to 5
  • A a direct bond, saturated or unsaturated, branched or
  • Z hydrogen, halogen, nitro, cyano, alkyl, alkenyl, alkynyl, cycloalkyl,
  • R 3 independently of one another alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, benzyl, alkoxy, alkenyloxy, alkynyloxy, phenyloxy, benzyloxy, alkoxyalkyl,
  • NR 3 2 morpholino, dialkylmorpholino, piperidino, piperazino, hydrazino,
  • R 4 hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, phenoxy, phenylthio, OH, SH, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynylthio, cycloalkylthio, cycloalkoxy, haloalkoxy, haloalkylthio, alkoxyalkyl,
  • NR 5 2 piperidino, morphoiino, piperazino, hydrazino or hydroxylamino or a radical of the formula
  • -A-SO 2 R 4 , -A-SOR 4 , -A-SR 4 , -AP (O) R 4 2 means.
  • R 1 (C 1 -C 6 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, (C 3 - C6 ) cycloalkyl, (C 3 -C 6 ) - Cycloalkenyl, the 5 groups independently of one another being unsubstituted or singly or multiply by the radicals halogen, cyano, nitro, mono- and di- (C r C 6 ) -alkylamino, (C 1 -C 4 ) -alkoxy, (C 2 -C 4 ) alkenyloxy, (C 2 -C 4 ) alkynyloxy, (C 1 -C 4 ) alkythio, (C 2 -C 4 ) alkenylthio, (C 2 -C 4 ) alkynylthio or may be substituted a rest of the formula
  • R 2 (C 1 -C 6 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, phenyl and benzyl, the 5 groups being independently unsubstituted or one or more times by the radicals halogen, cyano, nitro, mono- and di- (C 1 -C 4 ) alkylamino, (C 1 -C 4 ) alkoxy, halo- (C 1 -C 4 ) alkyl may be substituted or a radical of the formula
  • A a direct bond, saturated or unsaturated, branched or
  • Z hydrogen, halogen, nitro, cyano, (C 1 -C 6 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, (C 3 -C 6 ) cycloalkyl, (C 3 -C 6 ) cycloalkenyl, (C ⁇ CJ alkoxy, (C 2 -C 4 ) alkenyloxy, (C 2 -C 4 ) alkynyloxy, phenyl, phenoxy, halo (C 1 -C 4 ) alkyl, halo (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, halo (C 1 -C 4 ) alkylthio or a radical of the formula
  • R 3 independently of one another (C 1 -C 6 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, (C 3 - C 6 ) cycloalkyl, phenyl, benzyl, ( C 1 -C 4 ) alkoxy, (C 2 -C 4 ) alkenyloxy, (C 2 -C 4 ) alkynyloxy, phenyloxy, benzyloxy, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkylthio- (C 1 -C 4 ) -alkyl, halo- (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl, halo- (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alky
  • NR 3 2 morpholino, dialkylmorpholino, piperidino, piperazino, hydrazino,
  • R 4 hydrogen, (C 1 -C 6 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, (C 3 -C 6 ) cycloalkyl, phenyl, phenoxy, phenylthio , OH, SH, (C 1 -C 4) alkoxy, (C 2 -C 4) -alkyloxy, (C 2 - C 4) alkynyloxy, (C 1 -C 4) alkylthio, (C 2 -C 4 ) -alkenylthio, (C 2 -C 4 ) -alkynylthio, (C 3 -C 6 ) -cycloalkylthio, (C 3 -C 6 ) -cycloalkyloxy, halo- (C 1 -C 4 ) -alkoxy, halo- ( C 1 -C 4 ) alkylthio, (C
  • R 5 independently of each other (C 1 -C 6) -Alky !, (C2 - C4) alkenyl, (C 2 -C 4) -alkynyl, (C 3 - C 6) -CycIoalkyl, phenyl, benzyl, hydrogen, , (C 1 -C 4) alkoxy- (C 1 -C 4) alkyl, (C 1 - C 4) alkylthio (C 1 -C 4) alkyl or
  • NR 5 2 piperidino, morpholino, piperazino, hydrazino or hydroxylamino or a residue of the formula
  • -A-SO 2 R 4 , -A-SOR 4 , -A-SR 4 , -AP (O) R 4 2 means.
  • alkyl, alkoxy and alkylthio radicals and the corresponding unsaturated radicals can each be straight-chain or branched.
  • Halogen means fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
  • the invention also relates in particular to all stereoisomers and their mixtures which are encompassed by formula (I) or (II) but are not specifically defined.
  • the present invention also relates to a process for the preparation of the new compound of the formula (I) or (II), characterized in that a compound of the formula (III)
  • a suitable base for example NaHCO 3 , K 2 CO 3 or NEt 3
  • a polar solvent for example H 2 O, CH 3 OH, C 2 H 5 OH or CH 3 CN.
  • the compounds of the formula (III) can be prepared by various methods a 1 , a 2 , a 3 , a 4 known from the literature and by a new method a 5 according to the following formula scheme: a 1
  • R 1 as defined under the formulas (I) and (II) and
  • the compounds of the formulas (I) and (II) according to the invention are notable for an excellent pesticidal, in particular fungicidal, action. Fungal pathogens that have already penetrated into the plant tissue can be successfully combated curatively. This is particularly important and advantageous in the case of those fungal diseases which can no longer be effectively combated with the usual fungicides after infection has occurred.
  • the spectrum of activity of the claimed compounds covers a large number of economically important phytopathogenic fungi, such as, for example, Pyricularia oryzae, Phytophthora infestans,
  • the compounds according to the invention are also suitable for use in technical fields, for example as wood preservatives, as
  • the invention also relates to compositions which contain the compounds of the formula (I) or (II) in addition to suitable formulation auxiliaries.
  • Agents according to the invention generally contain from 1 to 95% by weight of the active compounds of the formula (I) or (II).
  • WP Wettable powder
  • EC emulsifiable concentrates
  • SC aqueous dispersions based on oil or water
  • SC suspoemulsions
  • DP dusts
  • mordants granules in the form of water-dispersible granules (WG)
  • ULV formulations microcapsules, Waxes or baits.
  • the necessary formulation aids such as inert materials, surfactants,
  • Solvents and other additives are also known and are described, for example, in:
  • combinations with other pesticidally active substances, fertilizers and / or growth regulators can also be produced, e.g. in the form of a finished formulation or as a tank mix.
  • Spray powders are preparations which are uniformly dispersible in water and which, in addition to the active substance, contain wetting agents, e.g.
  • polyethoxylated alkylphenols polyethoxylated fatty alcohols, alkyl or alkylphenyl sulfonates and dispersants, e.g. sodium lignosulfonate, 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, dibutylnaphthalene sulfonic acid
  • dispersants e.g. sodium lignosulfonate, 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, dibutylnaphthalene sulfonic acid
  • Solvents e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons with the addition of one or more emulsifiers.
  • emulsifiers for example
  • Alkylarylsulfonic acid calcium salts such as Ca-dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers,
  • Fatty alcohol polyglycol ether propylene oxide-ethylene oxide-sorbitan fatty acid ester, Polyoxyethylene sorbitan fatty acid ester or polyoxyethylene sorbitol ester.
  • Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g. Talc, natural clays such as kaolin, bentonite or pyrophillite or diatomaceous earth.
  • Finely divided solid substances e.g. Talc, natural clays such as kaolin, bentonite or pyrophillite or diatomaceous earth.
  • Granules can either be produced by spraying the active ingredient onto adsorbable, granulated inert material or by
  • Carriers such as sand, kaolinite or granulated inert material. Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granules, if desired in a mixture with fertilizers.
  • the active substance concentration in wettable powders is e.g. about 10 to 90 wt .-%, the rest of 100 wt .-% consists of conventional formulation components.
  • the active substance concentration can be approximately 5 to 80% by weight.
  • Dust-like formulations usually contain 5 to 20% by weight.
  • the active ingredient content depends in part on whether the active ingredient
  • Connection is liquid or solid and which connection is liquid or solid and which granulation aids, fillers etc. are used.
  • the active ingredient formulations mentioned may contain the customary adhesives, wetting agents, dispersants, emulsifiers, penetrants, solvents, fillers or carriers.
  • the concentrates which are commercially available, are diluted in the customary manner, e.g. for wettable powders, emulsifiable concentrates, dispersions and sometimes also for microgranules using water.
  • Dusty and granulated preparations and sprayable solutions are usually no longer diluted with other inert substances before use.
  • the active compounds according to the invention can be used in their commercially available formulations either alone or in combination with other fungicides known from the literature.
  • Anilazines benalaxyl, benodanil, benomyl, binapacryl, bitertanol, buthiobate,
  • Captafol Captan, Carbendazim, Carboxin, CGD-94240 F, Chlobenzthiazone, Chlorthalonil, Cymoxanil, Cyproconazole, Cyprofuram, Dichlofluanid, Dichiomezin, Diclobutrazol, Diethofencarb, Difluconazole, Dimethirorphimol, Dimethomim
  • Fentin acetate fentin hydroxide, fluaziram, fluobenzimine, fluorimide, flusilazole, flutolanil, flutriafol, folpet, fosetyl aluminum, fuberidazole, furalaxyl, furmecyclox. Guazatine, Hexaconazole, Imazalil, Iprobefos, Iprodione, Isoprothiolane,
  • Copper compounds such as Cu-oxychloride, Oxine-Cu, Cu-oxide, Mancozeb, Maneb, Mepronil, Metalaxyl, Methasulfocarb, Methfuroxam, Myclobutanil, Nabam,
  • active compounds according to the invention in particular those of the examples listed, can be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with other active compounds, such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • active compounds include, for example
  • Phosphoric acid esters carbamates, carboxylic acid esters, formamides,
  • Tin compounds, substances produced by microorganisms etc. Preferred mixing partners are:
  • Etrimphos Fenitrothion, Fenthion, Heptenophos, Parathion, Parathion-methyl, Phosalon, Pirimiphos-ethyl, Pirimiphos-methyl, Profenofos,
  • Cyclopropanecarboxylic acid (2-naphthylmethyl) ester (Ro 12-0470), cyromacin, DDT, dicofol, N- (3,5-dichloro-4- (1,1,2,2-tetrafiuoroethoxy) - phenylamino) carbonyl) -2, 6-difiuor-ben ⁇ S: ⁇ ide (XRD 473), diflubenzuron, N- (2,3-dihydro-3-methyl-1,2-thiazol-2-ylidenes) -2,4-xyfidine, dinobutone, dinocap.
  • Active ingredient concentrations of the use forms can be from 0.0001 to 100% by weight of active ingredient, preferably between 0.0001 to 1% by weight.
  • the Application takes place in a customary manner adapted to the application forms.
  • a dusting agent is obtained by mixing 10 parts by weight of active compound and 90 parts by weight of talc as an inert substance and comminuting them in a hammer mill.
  • a wettable powder which is readily dispersible in water is obtained by adding 25 parts by weight of active compound, 65 parts by weight of kaolin-containing quartz as
  • a dispersion concentrate which is easily dispersible in water is prepared by mixing 40 parts by weight of active compound with 1 part by weight of a
  • An emulsifiable concentrate can be prepared from 15 parts by weight
  • Granules can be produced from 2 to 15 parts by weight of active ingredient and
  • an inert granule carrier material such as attapulgite, pumice granulate and / or quartz sand.
  • a suspension of the wettable powder from example b) having a solids content of 30% is expediently used and sprayed onto the surface of an attapulgite granulate, dried and mixed intimately.
  • the proportion by weight of the wettable powder is about 5% and of the inert carrier material approx. 95% of the finished granulate.
  • Tomato plants of the "Rheinlands Ruhm” variety were uniformly wetted to the wet with 3 to 4 leaf stages with aqueous suspensions of the compounds according to the invention.
  • Infection conditions kept in a climatic chamber. The plants were then cultivated further in the greenhouse until the symptoms developed. The infection was assessed approximately 1 week after inoculation. The degree of infection of the plants was expressed in the infected leaf area, based on untreated infected plants, and is shown in Table III.
  • the plants were again placed in the climatic chamber overnight in order to stimulate the sporulation of the fungus.
  • the infestation was then assessed. The degree of infestation was expressed in the infested leaf area in comparison to the untreated, infected control plants and is shown in Table IV.

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne des sulfonylformamidrazones de formule générale (I) et leurs tautomères de formule générale (II) où R1 désigne un alkyle, alcényle, alkinyle, cycloalkyle,cycloalcényle, phényle portant éventuellement des substituants, ou un reste, tel que défini dans la description, de formule -A-NR22, -A-CO-R4, -A-SO2R4,-A-SOR4, -A-SR4 ou -S-P(O)R42, et R2 désigne un alkyle, alcényle, alkinyle, phényle, benzyle portant éventuellement des substituants, ou un reste tel que défini dans la description, de formule -CO-R2 ou -SO2R2. L'invention concerne en outre un procédé de fabrication de ces produits, des agents les renfermant, ainsi que leur utilisation pour la destruction des parasites végétaux et comme insecticides.The invention relates to sulfonylformamidrazones of general formula (I) and their tautomers of general formula (II) where R1 denotes an alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, phenyl optionally bearing substituents, or a residue, as defined in the description, of formula -A-NR22, -A-CO-R4, -A-SO2R4, -A-SOR4, -A-SR4 or -SP(O)R42, and R2 denotes an alkyl, alkenyl, alkinyl, phenyl, benzyl optionally bearing substituents, or a residue as defined in the description, of formula -CO-R2 or -SO2R2. The invention also relates to a process for the manufacture of these products, agents containing them, as well as their use for the destruction of plant pests and as insecticides.

Description

Beschreibung  description
Sulfonylformamidrazone, Verfahren zu ihrer Herstellung, sie enthaltende Mittel und ihre Verwendung gegen Pflanzenschädlinge Sulfonylformamidrazone, process for their preparation, compositions containing them and their use against plant pests
Die vorliegende Erfindung betrifft Sulfonylformamidrazone, Verfahren zu ihrer Herstellung, sie enthaltende Mittel sowie ihre Verwendung gegen The present invention relates to sulfonylformamide razones, processes for their preparation, compositions containing them and their use against
Pflanzenschädlinge, insbesondere als Fungizide.  Plant pests, in particular as fungicides.
Gegenstand der Erfindung sind Sulfonylformamidrazone der allgemeinen Formel (I) und deren Tautomere der allgemeinen Formel (II), The invention relates to sulfonylformamide zones of the general formula (I) and their tautomers of the general formula (II),
worin wherein
R1 = Alkyl, Alkenyl, Alkinyl, Cycloalkyl, Cycloalkenyl, wobei die 5 Gruppen R 1 = alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, the 5 groups
unabhängig voneinander unsubstituiert oder ein- oder mehrfach durch die Reste Halogen, Cyano, Nitro, Mono- und Dialkylamino, Alkoxy, Alkenyloxy, Alkinyloxy, Alkylthio, Alkenylthio, Alkinylthio substituiert sein können oder einen Rest der Formel  independently of one another, unsubstituted or mono- or polysubstituted by the radicals halogen, cyano, nitro, mono- and dialkylamino, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynylthio or a radical of the formula
( £n) >-- (£ n)> -
R2 = Alkyl, Alkenyl, Alkinyl, Phenyl und Benzyl, wobei die 5 Gruppen unabhängig voneinander unsubstituiert oder ein- oder mehrfach durch die Reste R 2 = alkyl, alkenyl, alkynyl, phenyl and benzyl, the 5 groups independently of one another unsubstituted or one or more times by the radicals
Halogen, Cyano, Nitro, Mono- und Dialkylamino, Alkoxy, Haloalkyl substituiert sein können oder einen Rest der Formel -C(O)R2', -SO2R2', worin Halogen, cyano, nitro, mono- and dialkylamino, alkoxy, haloalkyl can be substituted or a radical of the formula -C (O) R 2 ' , -SO 2 R 2' , wherein
R2' = Alkyl, Alkenyl, Alkinyl, Phenyl und Benzyl, wobei die 5 Gruppen unabhängig voneinander unsubstituiert oder ein- oder mehrfach durch die ResteR 2 ' = alkyl, alkenyl, alkynyl, phenyl and benzyl, the 5 groups independently of one another unsubstituted or one or more times by the radicals
Halogen, Cyano, Nitro, Mono- und Dialkylamino, Alkoxy, Haloalkyl substituiert sein können, bedeutet, Halogen, cyano, nitro, mono- and dialkylamino, alkoxy, haloalkyl can be substituted,
n = eine ganze Zahl von 0 - 5,  n = an integer from 0 to 5,
A = eine direkte Bindung, gesättigte oder ungesättigte, verzweigte oder  A = a direct bond, saturated or unsaturated, branched or
unverzweigte Alkylkette,  unbranched alkyl chain,
Z = Wasserstoff, Halogen, Nitro, Cyano, Alkyl, Alkenyl, Alkinyl, Cycloalkyl,  Z = hydrogen, halogen, nitro, cyano, alkyl, alkenyl, alkynyl, cycloalkyl,
Cycloalkenyl, Alkoxy, Alkenyloxy, Alkinyloxy, Phenyl, Phenoxy, Haloalkyl, Cycloalkenyl, alkoxy, alkenyloxy, alkynyloxy, phenyl, phenoxy, haloalkyl,
Haloalkoxy, Alkylthio, Haloalkylthio oder einen Rest der Formel Haloalkoxy, alkylthio, haloalkylthio or a radical of the formula
-A-NR3 2 bedeuten, worin -A-NR 3 2 , wherein
R3 = unabhängig voneinander Alkyl, Alkenyl, Alkinyl, Cycloalkyl, Phenyl, Benzyl, Alkoxy, Alkenyloxy, Alkinyloxy, Phenyloxy, Benzyloxy, Alkoxyalkyl, R 3 = independently of one another alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, benzyl, alkoxy, alkenyloxy, alkynyloxy, phenyloxy, benzyloxy, alkoxyalkyl,
Alkylthioalkyl, Haloalkoxyalkyl, Haloalkylthioalkyl, Haloalkyl, Wasserstoff oder einen Rest der Formel  Alkylthioalkyl, haloalkoxyalkyl, haloalkylthioalkyl, haloalkyl, hydrogen or a radical of the formula
-C(O)R4, -SO2R4, -SOR4, SR4 oder -C (O) R 4 , -SO 2 R 4 , -SOR 4 , SR 4 or
NR3 2 = Morpholino, Dialkylmorpholino, Piperidino, Piperazino, Hydrazino, NR 3 2 = morpholino, dialkylmorpholino, piperidino, piperazino, hydrazino,
Hydroxylamino, Phthalimido, Maleinimido, Dihydrophthalimido oder einen Rest der Formel  Hydroxylamino, phthalimido, maleimido, dihydrophthalimido or a radical of the formula
-A-C(O)R4 bedeutet, worin -AC (O) R 4 means in which
R4 = Wasserstoff, Alkyl, Alkenyl, Alkinyl, Cycloalkyl, Phenyl, Phenoxy, Phenylthio, OH, SH, Alkoxy, Alkenyloxy, Alkinyloxy, Alkylthio, Alkenylthio, Alkinylthio, Cycloalkylthio, Cycloalkoxy, Haloalkoxy, Haloalkylthio, Alkoxyalkyl, R 4 = hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, phenoxy, phenylthio, OH, SH, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynylthio, cycloalkylthio, cycloalkoxy, haloalkoxy, haloalkylthio, alkoxyalkyl,
Alkylthioalkyl oder  Alkylthioalkyl or
-NR5 2 bedeutet, worin R5 = unabhängig voneinander Alkyl, Alkenyl, Alkinyl, Cycloalkyl, Phenyl, Benzyl,-NR 5 2 means in which R 5 = independently of one another alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, benzyl,
Wasserstoff, Alkoxyalkyl, Alkylthioalkyl oder Hydrogen, alkoxyalkyl, alkylthioalkyl or
NR5 2 = Piperidino, Morphoiino, Piperazino, Hydrazino oder Hydroxylamino oder einen Rest der Formel NR 5 2 = piperidino, morphoiino, piperazino, hydrazino or hydroxylamino or a radical of the formula
-A-SO2R4, -A-SOR4, -A-SR4, -A-P(O)R4 2 bedeutet. -A-SO 2 R 4 , -A-SOR 4 , -A-SR 4 , -AP (O) R 4 2 means.
Bevorzugt sind Verbindungen der Formel (I) und (II), in denen Compounds of the formula (I) and (II) in which
R1 = (C1-C6)-Alkyl, (C2-C4)-Alkenyl, (C2-C4)-Alkinyl, (C3-C6)-Cycloalkyl, (C3-C6)- Cycloalkenyl, wobei die 5 Gruppen unabhängig voneinander unsubstituiert oder ein- oder mehrfach durch die Reste Halogen, Cyano, Nitro, Mono- und Di-(CrC6)-alkylamino, (C1-C4)-Alkoxy, (C2-C4)-Alkenyloxy, (C2-C4)-Alkinyloxy, (C1-C4)-Alkyithio, (C2-C4)-Alkenylthio, (C2-C4)-Alkinylthio substituiert sein können oder einen Rest der Formel R 1 = (C 1 -C 6 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, (C 3 - C6 ) cycloalkyl, (C 3 -C 6 ) - Cycloalkenyl, the 5 groups independently of one another being unsubstituted or singly or multiply by the radicals halogen, cyano, nitro, mono- and di- (C r C 6 ) -alkylamino, (C 1 -C 4 ) -alkoxy, (C 2 -C 4 ) alkenyloxy, (C 2 -C 4 ) alkynyloxy, (C 1 -C 4 ) alkythio, (C 2 -C 4 ) alkenylthio, (C 2 -C 4 ) alkynylthio or may be substituted a rest of the formula
R2 = (C1-C6)-Alkyl, (C2-C4)-Alkenyl, (C2-C4)-Alkinyl, Phenyl und Benzyl, wobei die 5 Gruppen unabhängig voneinander unsubstituiert oder ein- oder mehrfach durch die Reste Halogen, Cyano, Nitro, Mono- und Di-(C1-C4)-alkylamino, (C1-C4)-Alkoxy, Halo-(C1-C4)-alkyl substituiert sein können oder einen Rest der Formel R 2 = (C 1 -C 6 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, phenyl and benzyl, the 5 groups being independently unsubstituted or one or more times by the radicals halogen, cyano, nitro, mono- and di- (C 1 -C 4 ) alkylamino, (C 1 -C 4 ) alkoxy, halo- (C 1 -C 4 ) alkyl may be substituted or a radical of the formula
-C(O)R2', -SO2R2', worin -C (O) R 2 ' , -SO 2 R 2' , wherein
R2' = (C1-C6)-Alkyl, (C2-C4)-Alkenyl, (C2-C4)-Alkinyl, Phenyl und Benzyl, wobei die 5 Gruppen unabhängig voneinander unsubstituiert oder ein- oder mehrfach durch die Reste Halogen, Cyano, Nitro, Mono- und Di-(C1-C4)-alkylamino, (C1-C4)-Alkoxy, Halo-(C1-C4)-alkyl substituiert sein können, bedeutet, n = eine ganze Zahl von 0 - 5, R 2 ' = (C 1 -C 6 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, phenyl and benzyl, the 5 groups being independently unsubstituted or one or more times by the radicals halogen, cyano, nitro, mono- and di- (C 1 -C 4 ) alkylamino, (C 1 -C 4 ) alkoxy, halo- (C 1 -C 4 ) alkyl may be substituted , n = an integer from 0 - 5,
A = eine direkte Bindung, gesättigte oder ungesättigte, verzweigte oder  A = a direct bond, saturated or unsaturated, branched or
unverzweigte Alkylkette, Z = Wasserstoff, Halogen, Nitro, Cyano, (C1-C6)-Alkyl, (C2-C4)-Alkenyi, (C2-C4)- Alkinyl, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkenyl, (C^CJ-Alkoxy, (C2-C4)- Alkenyloxy, (C2-C4)-AIkinyloxy, Phenyl, Phenoxy, Halo-(C1-C4)-alkyl, Halo-(C1- C4)-alkoxy, (C1-C4)-Alkylthio, Halo-(C1-C4)-alkylthio oder einen Rest der Formel unbranched alkyl chain, Z = hydrogen, halogen, nitro, cyano, (C 1 -C 6 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, (C 3 -C 6 ) cycloalkyl, (C 3 -C 6 ) cycloalkenyl, (C ^ CJ alkoxy, (C 2 -C 4 ) alkenyloxy, (C 2 -C 4 ) alkynyloxy, phenyl, phenoxy, halo (C 1 -C 4 ) alkyl, halo (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, halo (C 1 -C 4 ) alkylthio or a radical of the formula
-A-NR3 2 bedeuten, worin -A-NR 3 2 , wherein
R3 = unabhängig voneinander (C1-C6)-Alkyl, (C2-C4)-Alkenyl, (C2-C4)-Alkinyl, (C3- C6)-Cycloalkyl, Phenyl, Benzyl, (C1-C4)-Alkoxy, (C2-C4)-Alkenyloxy, (C2-C4)- Alkinyloxy, Phenyloxy, Benzyloxy, (C1-C4)-Alkoxy-(C1-C4)-alkyl, (C1-C4)- Alkylthio-(C1-C4)-alkyl, Halo-(C1-C4)-alkoxy-(C1-C4)-alkyl, Halo-(C1-C4)-alkylthio- (C1-C4)-alkyl, Halo-(C1-C4)-alkyl, Wasserstoff oder einen Rest der Formel R 3 = independently of one another (C 1 -C 6 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, (C 3 - C 6 ) cycloalkyl, phenyl, benzyl, ( C 1 -C 4 ) alkoxy, (C 2 -C 4 ) alkenyloxy, (C 2 -C 4 ) alkynyloxy, phenyloxy, benzyloxy, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkylthio- (C 1 -C 4 ) -alkyl, halo- (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl, halo- (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkyl, halo (C 1 -C 4 ) alkyl, hydrogen or a radical of the formula
-C(O)R4, -SO2R4, -SOR4, SR4 oder -C (O) R 4 , -SO 2 R 4 , -SOR 4 , SR 4 or
NR3 2= Morpholino, Dialkylmorpholino, Piperidino, Piperazino, Hydrazino, NR 3 2 = morpholino, dialkylmorpholino, piperidino, piperazino, hydrazino,
Hydroxylamino, Phthalimido, Maleinimido, Dihydrophthalimido oder einen Rest der Formel  Hydroxylamino, phthalimido, maleimido, dihydrophthalimido or a radical of the formula
-A-C(O)R4 bedeutet, worin -AC (O) R 4 means in which
R4 = Wasserstoff, (C1-C6)-Alkyl, (C2-C4)-Alkenyl, (C2-C4)-Alkinyl, (C3-C6)-Cycloalkyl, Phenyl, Phenoxy, Phenylthio, OH, SH, (C1-C4)-Alkoxy, (C2-C4)-Alkyloxy, (C2- C4)-Alkinyloxy, (C1-C4)-Alkylthio, (C2-C4)-Alkenylthio, (C2-C4)-Aikinylthio, (C3- C6)-Cycloalkylthio, (C3-C6)-Cycloalkyloxy, Halo-(C1-C4)-alkoxy, Halo-(C1-C4)- alkylthio, (C1-C4)-Alkoxy-(C1-C4)-alkyl, (C1-C4)-Alkylthio-(C1-C4)-alkyl, R 4 = hydrogen, (C 1 -C 6 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, (C 3 -C 6 ) cycloalkyl, phenyl, phenoxy, phenylthio , OH, SH, (C 1 -C 4) alkoxy, (C 2 -C 4) -alkyloxy, (C 2 - C 4) alkynyloxy, (C 1 -C 4) alkylthio, (C 2 -C 4 ) -alkenylthio, (C 2 -C 4 ) -alkynylthio, (C 3 -C 6 ) -cycloalkylthio, (C 3 -C 6 ) -cycloalkyloxy, halo- (C 1 -C 4 ) -alkoxy, halo- ( C 1 -C 4 ) alkylthio, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkyl,
-NR5 2 bedeutet, worin -NR 5 2 means in which
R5 = unabhängig voneinander (C1-C6)-Alky!, (C2-C4)-Alkenyl, (C2-C4)-Alkinyl, (C3- C6)-CycIoalkyl, Phenyl, Benzyl, Wasserstoff, (C1-C4)-Alkoxy-(C1-C4)-alkyl, (C1- C4)Alkylthio-(C1-C4)-alkyl oder R 5 = independently of each other (C 1 -C 6) -Alky !, (C2 - C4) alkenyl, (C 2 -C 4) -alkynyl, (C 3 - C 6) -CycIoalkyl, phenyl, benzyl, hydrogen, , (C 1 -C 4) alkoxy- (C 1 -C 4) alkyl, (C 1 - C 4) alkylthio (C 1 -C 4) alkyl or
NR5 2 = Piperidino, Morpholino, Piperazino, Hydrazino oder Hydroxylamino oder einen Rest der Formel NR 5 2 = piperidino, morpholino, piperazino, hydrazino or hydroxylamino or a residue of the formula
-A-SO2R4, -A-SOR4, -A-SR4, -A-P(O)R4 2 bedeutet. -A-SO 2 R 4 , -A-SOR 4 , -A-SR 4 , -AP (O) R 4 2 means.
In der Formel (I) bzw. (II) können Alkyl-, Alkoxy- und Alkylthioreste sowie die entsprechenden ungesättigten Reste jeweils geradkettig oder verzweigt sein. In the formula (I) or (II), alkyl, alkoxy and alkylthio radicals and the corresponding unsaturated radicals can each be straight-chain or branched.
Halogen bedeutet Fluor, Chlor, Brom oder Jod, vorzugsweise Fluor, Chlor oder Brom, insbesondere Fluor oder Chlor. Halogen means fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
Gegenstand der Erfindung sind insbesondere auch alle Stereoisomeren und deren Gemische, die von Formel (I) oder (II) umfaßt, jedoch nicht spezifisch definiert sind. The invention also relates in particular to all stereoisomers and their mixtures which are encompassed by formula (I) or (II) but are not specifically defined.
Gegenstand der vorliegenden Erfindung ist auch ein Verfahren zur Herstellung der neuen Verbindung der Formel (I) oder (II), dadurch gekennzeichnet, daß eine Verbindung der Formel (III) The present invention also relates to a process for the preparation of the new compound of the formula (I) or (II), characterized in that a compound of the formula (III)
R1 - SO2 - CN (III), worin R1 die unter den Formeln (I) bzw. (II) genannte Bedeutung besitzt, mit einer Verbindung der Formel (IV) R 1 - SO 2 - CN (III), in which R 1 has the meaning given under the formulas (I) or (II), with a compound of the formula (IV)
R2 - NH - NH2 (IV), worin R2 die unter den Formeln (I) und (II) beschriebene Bedeutung hat, oder eines Salzes dieser Verbindung, in Gegenwart einer geeigneten Base, beispielsweise NaHCO3, K2CO3 oder NEt3 in einem polaren Lösungsmittel, beispielsweise H2O, CH3OH, C2H5OH oder CH3CN, umgesetzt wird. R 2 - NH - NH 2 (IV), in which R 2 has the meaning described under the formulas (I) and (II), or a salt of this compound, in the presence of a suitable base, for example NaHCO 3 , K 2 CO 3 or NEt 3 is reacted in a polar solvent, for example H 2 O, CH 3 OH, C 2 H 5 OH or CH 3 CN.
Die Verbindungen der Formel (III) können nach verschiedenen lieteraturbekannten Methoden a1, a2, a3, a4 sowie nach einer neuen Methode a5 gemäß folgendem Formelschema hergestellt werden: a1 The compounds of the formula (III) can be prepared by various methods a 1 , a 2 , a 3 , a 4 known from the literature and by a new method a 5 according to the following formula scheme: a 1
a2 a 2
a3 a 3
a4 - a 4 -
a5 a 5
worin wherein
R1 = wie unter den Formeln (I) und (II) angegeben definiert sind undR 1 = as defined under the formulas (I) and (II) and
X = Cl oder Br bedeutet. Lit. (a1-a4): Tetrahedron Lett. Bd. 39, 3351 (1969). X = Cl or Br. Lit. (a 1 -a 4 ): Tetrahedron Lett. 39: 3351 (1969).
J. Chem. Soc. Sect. D. Chem. Commun.1969, 1187. J. Chem. Soc. Sect. D. Chem. Commun. 1969, 1187.
DE 2 248 940 DE 2 248 940
US 3,755,306  US 3,755,306
DE 1 930 014  DE 1 930 014
Organic Synthesis Vol. 57, 88 (1977)  Organic Synthesis Vol. 57, 88 (1977)
J. Chem. Soc. Royal Netherlands 94 (1), 12 (1975) J. Chem. Soc. Royal Netherlands 94 (1), 12 (1975)
3. Chem. Soc, Chem. Commun. 1968, 440. Die erfindungsgemäßen Verbindungen der Formeln (I) und (II) zeichnen sich durch eine hervorragende pesticide, insbesondere fungizide Wirkung aus. Bereits in das pflanzliche Gewebe eingedrungene pilzliche Krankheitserreger lassen sich erfolgreich kurativ bekämpfen. Dies ist besonders wichtig und vorteilhaft bei solchen Pilzkrankheiten, die nach eingetretener Infektion mit den sonst üblichen Fungiziden nicht mehr wirksam bekämpft werden können. Das Wirkungsspektrum der beanspruchten Verbindungen erfaßt eine Vielzahl wirtschaftlich bedeutender, phytopathogener Pilze, wie z.B. Pyricularia oryzae, Phytophthora infestans, 3. Chem. Soc, Chem. Commun. 1968, 440. The compounds of the formulas (I) and (II) according to the invention are notable for an excellent pesticidal, in particular fungicidal, action. Fungal pathogens that have already penetrated into the plant tissue can be successfully combated curatively. This is particularly important and advantageous in the case of those fungal diseases which can no longer be effectively combated with the usual fungicides after infection has occurred. The spectrum of activity of the claimed compounds covers a large number of economically important phytopathogenic fungi, such as, for example, Pyricularia oryzae, Phytophthora infestans,
Plasmopara viticola, Leptosphaeria nodorum und verschiedene Rostpilze. Plasmopara viticola, Leptosphaeria nodorum and various rust fungi.
Die erfindungsgemaßen Verbindungen eignen sich daneben auch für den Einsatz in technischen Bereichen, beispielsweise als Holzschutzmittel, als The compounds according to the invention are also suitable for use in technical fields, for example as wood preservatives, as
Konservierungsmittel in Anstrichfarben, in Kühlschmiermittel für die Preservatives in paints, in cooling lubricants for the
Metallbearbeitung oder als Konservierungsmittel in Bohr- und Schneidölen. Metalworking or as a preservative in drilling and cutting oils.
Gegenstand der Erfindung sind auch Mittel, die die Verbindungen der Formel (I) oder (II) neben geeigneten Formulierungshilfsmitteln enthalten. Die The invention also relates to compositions which contain the compounds of the formula (I) or (II) in addition to suitable formulation auxiliaries. The
erfindungsgemaßen Mittel enthalten die Wirkstoffe der Formel (I) oder (II) im allgemeinen zu 1 bis 95 Gew.-%. Agents according to the invention generally contain from 1 to 95% by weight of the active compounds of the formula (I) or (II).
Sie können auf verschiedene Art formuliert werden, je nachdem wie es durch die biologischen und/oder chemisch-physikalischen Parameter vorgegeben ist. Als Formulierungsmöglichkeiten kommen daher in Frage: They can be formulated in different ways, depending on how it is specified by the biological and / or chemical-physical parameters. Possible formulations are therefore:
Spritzpulver (WP), emulgierbare Konzentrate (EC), wäßrige Dispersionen auf Öl-oder Wasserbasis (SC), Suspoemulsionen (SC), Stäubemittel (DP), Beizmittel, Granulate in Form von wasserdispergierbaren Granulaten (WG), ULV-Formulierungen, Mikrokapseln, Wachse oder Köder.  Wettable powder (WP), emulsifiable concentrates (EC), aqueous dispersions based on oil or water (SC), suspoemulsions (SC), dusts (DP), mordants, granules in the form of water-dispersible granules (WG), ULV formulations, microcapsules, Waxes or baits.
Diese einzelnen Formulierungstypen sind im Prinzip bekannt und werden These individual types of formulation are known in principle and will
beispielsweise beschrieben in: Winnacker-Küchler, "Chemische Technologie", Band 7, C. Hauser Verlag München, 4. Aufl. 1986; van Falkenberg, "Pesticide described for example in: Winnacker-Küchler, "Chemische Technologie", Volume 7, C. Hauser Verlag Munich, 4th ed. 1986; van Falkenberg, "Pesticide
Formulations", Marcel Dekker N.Y., 2nd Ed. 1972-73; K. Martens, "Spray Drying Handbook", 3rd Ed. 1979, G. Goodwin Ltd., London. Formulations ", Marcel Dekker NY, 2nd Ed. 1972-73; K. Martens," Spray Drying Handbook ", 3rd Ed. 1979, G. Goodwin Ltd., London.
Die notwendigen Formulierungshilfsmittel wie Inertmaterialien, Tenside, The necessary formulation aids such as inert materials, surfactants,
Lösungsmittel und weitere Zusatzstoffe sind ebenfalls bekannt und werden beispielsweise beschrieben in:  Solvents and other additives are also known and are described, for example, in:
Watkins, "Handbook of Insecticide Dust Diluents and Carrier", 2nd Ed., Dariand Books, Caldwell N.J.; H.v.Olphen, "Introduction to Clay Colloid Chemistry, 2nd Ed., J. Wiley & Sons, N.Y.; Mardsen, "Solvents Guide", 2nd Ed., Interscience, N.Y. 1950; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1961; Schönfeldt, "Grenzflächenaktive Äthylenoxidaddukte", Wiss.  Watkins, "Handbook of Insecticide Dust Diluents and Carrier", 2nd Ed., Dariand Books, Caldwell N.J .; HvOlphen, "Introduction to Clay Colloid Chemistry, 2nd Ed., J. Wiley & Sons, NY; Mardsen," Solvents Guide ", 2nd Ed., Interscience, NY 1950; McCutcheon's" Detergents and Emulsifiers Annual ", MC Publ. Corp ., Ridgewood NJ; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., NY 1961; Schönfeldt, "Interface-active Ethylene Oxide Adducts", Wiss.
Verlagsgesell., Stuttgart 1916; Winnacker-Küchler, "Chemische Technologie", Band 7, C. Hauser Verlag München, 1. Aufl. 1986.  Publishing company, Stuttgart 1916; Winnacker-Küchler, "Chemical Technology", Volume 7, C. Hauser Verlag Munich, 1st ed. 1986.
Auf der Basis dieser Formulierungen lassen sich auch Kombinationen mit anderen pestizid wirksamen Stoffen, Düngemitteln und/oder Wachstumsregulatoren herstellen, z.B. in Form einer Fertigformulierung oder als Tankmix. Based on these formulations, combinations with other pesticidally active substances, fertilizers and / or growth regulators can also be produced, e.g. in the form of a finished formulation or as a tank mix.
Spritzpulver sind in Wasser gleichmäßig dispergierbare Präparate, die neben dem Wirkstoff außer einem Verdünnungs- oder Inertstoff noch Netzmittel, z.B. Spray powders are preparations which are uniformly dispersible in water and which, in addition to the active substance, contain wetting agents, e.g.
polyethoxylierte Alkylphenole, polyethoxylierte Fettalkohole, Alkyl- oder Alkylphenyl-sulfonate und Dispergiermittel, z.B. ligninsulfonsaures Natrium, 2,2'-dinaphthylmethan-6,6'-disulfonsaures Natrium, dibutylnaphthalin-sulfonsaures  polyethoxylated alkylphenols, polyethoxylated fatty alcohols, alkyl or alkylphenyl sulfonates and dispersants, e.g. sodium lignosulfonate, 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, dibutylnaphthalene sulfonic acid
Natrium oder auch oleylmethyltaurinsaures Natrium enthalten. Emulgierbare Contain sodium or oleylmethyl tauric acid sodium. Emulsifiable
Konzentrate werden durch Auflösen des Wirkstoffes in einem organischen Concentrates are made by dissolving the active ingredient in an organic
Lösungsmittel, z.B. Butanol, Cyclohexanon, Dimethylformamid, Xylol oder auch höhersiedenden Aromaten oder Kohlenwasserstoffen unter Zusatz von einem oder mehreren Emulgatoren hergestellt. Als Emulgatoren können beispielsweise Solvents, e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons with the addition of one or more emulsifiers. As emulsifiers, for example
verwendet werden: be used:
Alkylarylsulfonsaure Calcium-Salze wie Ca-dodecylbenzolsulfonat oder nichtionische Emulgatoren wie Fettsäurepolyglykolester, Alkylarylpolyglykolether,  Alkylarylsulfonic acid calcium salts such as Ca-dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers,
Fettalkohoipolyglykolether, Propylenoxid-Ethylenoxid-Sorbitanfettsäureester, Polyoxyethylensorbitan-Fettsäureester oder Polyoxyethylensorbitester. Fatty alcohol polyglycol ether, propylene oxide-ethylene oxide-sorbitan fatty acid ester, Polyoxyethylene sorbitan fatty acid ester or polyoxyethylene sorbitol ester.
Stäubemittel erhält man durch Vermählen des Wirkstoffes mit fein verteilten festen Stoffen, z.B. Talkum, natürlichen Tonen wie Kaolin, Bentonit oder Pyrophillit oder Diatomeenerde. Granulate können entweder durch Verdüsen des Wirkstoffes auf adsorptionsfähiges, granuliertes Inertmaterial hergestellt werden oder durch Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g. Talc, natural clays such as kaolin, bentonite or pyrophillite or diatomaceous earth. Granules can either be produced by spraying the active ingredient onto adsorbable, granulated inert material or by
Aufbringen von Wirkstoffkonzentraten mittels Klebemitteln, z.B. Polyvinylalkohol, polyacrylsaürem Natrium oder auch Mineralölen, auf die Oberfläche von Application of active ingredient concentrates using adhesives, e.g. Polyvinyl alcohol, polyacrylic acid sodium or mineral oils, on the surface of
Trägerstoffen wie Sand, Kaolinite oder von granuliertem Inertmaterial. Auch können geeignete Wirkstoffe in der für die Herstellung von Düngemittelgranulaten üblichen Weise - gewünschtenfalls in Mischung mit Düngemitteln - granuliert werden. Carriers such as sand, kaolinite or granulated inert material. Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granules, if desired in a mixture with fertilizers.
In Spritzpulvern beträgt die Wirkstoffkonzentration z.B. etwa 10 bis 90 Gew.-%, der Rest zu 100 Gew.-% besteht aus üblichen Formulierungsbestandteilen. Bei emulgierbaren Konzentraten kann die Wirkstoffkonzentration etwa 5 bis 80 Gew.-% betragen. Staubförmige Formulierungen enthalten meistens 5 bis 20 Gew.-%. Bei Granulaten hängt der Wirkstoffgehalt zum Teil davon ab, ob die wirksame The active substance concentration in wettable powders is e.g. about 10 to 90 wt .-%, the rest of 100 wt .-% consists of conventional formulation components. In the case of emulsifiable concentrates, the active substance concentration can be approximately 5 to 80% by weight. Dust-like formulations usually contain 5 to 20% by weight. In the case of granules, the active ingredient content depends in part on whether the active ingredient
Verbindung flüssig oder fest vorliegt und welche Verbindung flüssig oder fest vorliegt und welche Granulierhilfsmittel, Füllstoffe usw. verwendet werden. Connection is liquid or solid and which connection is liquid or solid and which granulation aids, fillers etc. are used.
Daneben enthalten die genannten Wirkstofformulierungen gegebenenfalls die jeweils üblichen Haft-, Netz-, Dispergier-, Emulgier-, Penetrations-, Lösungsmittel, Füll- oder Trägerstoffe. In addition, the active ingredient formulations mentioned may contain the customary adhesives, wetting agents, dispersants, emulsifiers, penetrants, solvents, fillers or carriers.
Zur Anwendung werden die in handelsüblicher Form vorliegenden Konzentrate gegebenenfalls in üblicher Weise verdünnt, z.B. bei Spritzpulvern, emulgierbaren Konzentraten, Dispersionen und teilweise auch bei Mikrogranulaten mittels Wasser. For use, the concentrates, which are commercially available, are diluted in the customary manner, e.g. for wettable powders, emulsifiable concentrates, dispersions and sometimes also for microgranules using water.
Staubförmige und granulierte Zubereitungen sowie verspruhbare Lösungen werden vor der Anwendung üblicherweise nicht mehr mit weiteren inerten Stoffen verdünnt. Dusty and granulated preparations and sprayable solutions are usually no longer diluted with other inert substances before use.
Mit den äußeren Bedingungen wie Temperatur, Feuchtigkeit u.a. variiert die erforderliche Aufwandmenge. Sie kann innerhalb weiter Grenzen schwanken, z.B. zwischen 0,005 und 10,0 kg/ha oder mehr Aktivsubstanz, vorzugsweise liegt sie jedoch zwischen 0,01 und 5 kg/ha. The varies with the external conditions such as temperature, humidity and others required application rate. It can vary within wide limits, for example between 0.005 and 10.0 kg / ha or more of active substance, but is preferably between 0.01 and 5 kg / ha.
Die erfindungsgemäßen Wirkstoffe können in ihren handelsüblichen Formulierungen entweder allein oder in Kombination mit weiteren, literaturbekannten Fungiziden angewendet werden. The active compounds according to the invention can be used in their commercially available formulations either alone or in combination with other fungicides known from the literature.
Als literaturbekannte Fungizide, die erfindungsgemäß mit den Verbindungen der Formeln (I) und (II) kombiniert werden können, sind z.B. folgende Produkte zu nennen: Examples of fungicides known from the literature which can be combined according to the invention with the compounds of the formulas (I) and (II) are, for example to name the following products:
Anilazine, Benalaxyl, Benodanil, Benomyl, Binapacryl, Bitertanol, Buthiobat, Anilazines, benalaxyl, benodanil, benomyl, binapacryl, bitertanol, buthiobate,
Captafol, Captan, Carbendazim, Carboxin, CGD-94240 F, Chlobenzthiazone, Chlorthalonil, Cymoxanil, Cyproconazole, Cyprofuram, Dichlofluanid, Dichiomezin, Diclobutrazol, Diethofencarb, Difluconazole, Dimethirimol, Dimethomorph,  Captafol, Captan, Carbendazim, Carboxin, CGD-94240 F, Chlobenzthiazone, Chlorthalonil, Cymoxanil, Cyproconazole, Cyprofuram, Dichlofluanid, Dichiomezin, Diclobutrazol, Diethofencarb, Difluconazole, Dimethirorphimol, Dimethomim
Diniconazole, Dinocap, Dithianon, Dodemorph, Dodine, Edifenfos, Ethirimol, Etridiazol, Fenarimol, Fenfuram, Fenpiclonil, Fenpropidin, Fenpropomorph,  Diniconazole, Dinocap, Dithianon, Dodemorph, Dodine, Edifenfos, Ethirimol, Etridiazol, Fenarimol, Fenfuram, Fenpiclonil, Fenpropidin, Fenpropomorph,
Fentinacetat, Fentinhydroxid, Fluaziram, Fluobenzimine, Fluorimide, Flusilazole, Flutolanil, Flutriafol, Folpet, Fosetylaluminium, Fuberidazole, Furalaxyl, Furmecyclox. Guazatine, Hexaconazole, Imazalil, Iprobenfos, Iprodione, Isoprothiolane, Fentin acetate, fentin hydroxide, fluaziram, fluobenzimine, fluorimide, flusilazole, flutolanil, flutriafol, folpet, fosetyl aluminum, fuberidazole, furalaxyl, furmecyclox. Guazatine, Hexaconazole, Imazalil, Iprobefos, Iprodione, Isoprothiolane,
Kupferverbindungen wie Cu-oxychlorid, Oxine-Cu, Cu-oxide, Mancozeb, Maneb, Mepronil, Metalaxyl, Methasulfocarb, Methfuroxam, Myclobutanil, Nabam, Copper compounds such as Cu-oxychloride, Oxine-Cu, Cu-oxide, Mancozeb, Maneb, Mepronil, Metalaxyl, Methasulfocarb, Methfuroxam, Myclobutanil, Nabam,
Nitrothalidopropyl, Nuarimol, Ofurace, Oxadixyl, Oxycarboxin, Penconazol, Nitrothalidopropyl, Nuarimol, Ofurace, Oxadixyl, Oxycarboxin, Penconazol,
Pencycuron, PP 969, Probenazole, Probineb, Prochloraz, Procymidon, Pencycuron, PP 969, probenazole, probineb, prochloraz, procymidon,
Propamocarb, Propiconazol, Prothiocarb, Pyracarbolid, Pyrifenox, Pyroquilon, Rabenzazole, Schwefel, Tebuconazole, Thiabendazole, Thiofanatemethal, Thiram, Tolclofos-methyl, Tolylfluanid, Triadimefon, Triadimenol, Tricyclazole, Tridemorph, Triflumizol, Triforine, Vinchlozolin, Zineb, Natrium-dodecylsulfonat, Natrium- dodecylsulfat, Natrium-C13/C15-alkoholethersulfonat, Natrium- cetostearylphosphatester, Dioctyl-natriumsuifosuccinat, Natrium- isopropylnaphthalinsulfonat, Natrium-methylenbisnaphthalinsulfonat, Cetyl-trimethyl- ammoniumchlorid, Salze von langkettigen primären, sekundären oder tertiären Aminen, Alkyl-propylenamine, Lauryl-pyrimidiniumbromid, ethoxylierte quaternierte Fettamine, Alkyl-dimethyl-benzyl-ammoniumchlorid und 1-Hydroxyethyl-2-alkyl-imidazoiin. Propamocarb, propiconazole, prothiocarb, pyracarbolide, pyrifenox, pyroquilon, rabenzazole, sulfur, tebuconazole, thiabendazole, thiofanatemethal, thiram, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, tricyclazole, trifluorodoline, trifluoromoline, trifluoromoline, trifluoromoline, trifluoromoline, trifluoromoline, trifluoromoline, trifluoromoline, trifluoromoline, trifluoromoline, trifluoromoline, trifluoroblone, trifluoromolone, trifluorocarbone, tri Sodium dodecyl sulfate, sodium C13 / C15 alcohol ether sulfonate, sodium cetostearyl phosphate ester, dioctyl sodium suifosuccinate, sodium isopropylnaphthalene sulfonate, sodium methylene bisnaphthalene sulfonate, cetyl trimethyl ammonium chloride, salts of long-chain primary, secondary or tertiary amines, alkyl propylene amines, lauryl pyrimidinium bromide, ethoxylated quaternized fatty amines, alkyl dimethyl benzyl ammonium chloride and 1-hydroxyethyl-2-alkyl imidazoiin.
Die oben genannten Kombinationspartner stellen bekannte Wirkstoffe dar, die zum großen Teil in C.R. Worthing, S.B. Walker, The Pesticide Manual, 7. Aufl. (1983), British Crop Protection Council, beschrieben sind. The above-mentioned combination partners are known active ingredients, which are largely in C.R. Worthing, S.B. Walker, The Pesticide Manual, 7th ed. (1983), British Crop Protection Council.
Darüberhinaus können die erfindungsgemäßen Wirkstoffe, insbesondere die der aufgeführten Beispiele, in ihren handelsüblichen Formulierungen sowie in den aus diesen Formulierungen bereiteten Anwendungsformen in Mischung mit anderen Wirkstoffe, wie Insektiziden, Lockstoffen, Sterilantien, Akariziden, Nematiziden, Fungiziden, wachstumsregulierenden Stoffe oder Herbiziden vorliegen. Zu den Insektiziden zählen beispielsweise In addition, the active compounds according to the invention, in particular those of the examples listed, can be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with other active compounds, such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, growth-regulating substances or herbicides. Insecticides include, for example
Phosphorsäureester, Carbamate, Carbonsäureester, Formamide,  Phosphoric acid esters, carbamates, carboxylic acid esters, formamides,
Zinnverbindungen, durch Mikroorganismen hergestellte Stoffe u.a.. Bevorzugte Mischungspartner sind: Tin compounds, substances produced by microorganisms etc. Preferred mixing partners are:
1. aus der Gruppe der Phosphorsäureester 1. from the group of phosphoric acid esters
Azinphos-ethyl, Azinphos-methyl, 1-(4-Chlorphenyl)-4-(O-ethyl, S-propyl)- phosphoryi-oxypyrazol (TIA-230), Chlorpyrifos, Coumaphos, Demeton, Demeton-S-methyl, Diazinon, Dichlorvos, Dimethoat, Ethoprophos,  Azinphos-ethyl, Azinphos-methyl, 1- (4-chlorophenyl) -4- (O-ethyl, S-propyl) -phosphoryi-oxypyrazole (TIA-230), Chlorpyrifos, Coumaphos, Demeton, Demeton-S-methyl, diazinon , Dichlorvos, dimethoate, ethoprophos,
Etrimphos, Fenitrothion, Fenthion, Heptenophos, Parathion, Parathion- methyl, Phosalon, Pirimiphos-ethyl, Pirimiphos-methyl, Profenofos,  Etrimphos, Fenitrothion, Fenthion, Heptenophos, Parathion, Parathion-methyl, Phosalon, Pirimiphos-ethyl, Pirimiphos-methyl, Profenofos,
Prothiofos, Sulprofos, Triazophos, Trichlorphon.  Prothiofos, Sulprofos, Triazophos, Trichlorphon.
2. aus der Gruppe der Carbamate 2. from the group of carbamates
Aldicarb, Bendiocarb, BPMC (2-(1-Methylpropyl)-phenylmethyl-carbamat), Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran, Carbosulfan, Cloethocarb, Isoprocarb, Methomyl, Oxamyl, Pirimicarb, Promecarb, Propoxur, Thiodicarb. 3. aus der Gruppe der Carbonsäureester Aldicarb, Bendiocarb, BPMC (2- (1-methylpropyl) phenylmethyl carbamate), Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran, Carbosulfan, Cloethocarb, Isoprocarb, Methomyl, Oxamyl, Pirimicarb, Promecarb, Propoxur, Thiodicarb. 3. from the group of carboxylic acid esters
Allethrin, Alphamethrin, Bioaliethrin, Bioresmethrin, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cypermethrin, Deltamethrin, 2,2-DimethyI-3-(2-chlor-2- trifluormethylvinyl)-cyclopropancarbonsäure-(alpha-cyano-3-phenyl-2-methylbenzyl)ester (FMC 54800), Fenpropathrin, Fenfluthrin, Fenvalerat,  Allethrin, Alphamethrin, Bioaliethrin, Bioresmethrin, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cypermethrin, Deltamethrin, 2,2-DimethyI-3- (2-chloro-2-trifluoromethylvinyl) -cyclopropanecarboxylic acid- (alpha-cyano-3-phenyl-2-methyl-2-phenyl-2-methyl) ) ester (FMC 54800), fenpropathrin, fenfluthrin, fenvalerate,
Flucythrinate, Flumethrin, Fluvalinate, Permethrin, Resmethrin, Tralomethrin.  Flucythrinate, flumethrin, fluvalinate, permethrin, resmethrin, tralomethrin.
4. aus der Gruppe der Formamidine 4. from the group of formamidines
Amitraz, Chlordimeform.  Amitraz, chlorordime form.
5. aus der Gruppe der Zinnverbindungen 5. from the group of tin compounds
Azocyclotin, Cyhexatin, Fenbutatinoxid.  Azocyclotin, Cyhexatin, Fenbutatinoxid.
6. sonstige . 6. other.
Abamektin, Bacillus thuringiensis, Bensultap, Binapacryl, Bromopropylate, Buprofecin, Camphechlor, Cartap, Chlorbenzilate, Chlorfluazuron, 2-(4- ChlorphenyI)-4,5-diphenylthiophen (UBI-T 930), Chlofentezine,  Abamectin, Bacillus thuringiensis, Bensultap, Binapacryl, Bromopropylate, Buprofecin, Camphechlor, Cartap, Chlorbenzilate, Chlorfluazuron, 2- (4-ChlorphenyI) -4,5-diphenylthiophene (UBI-T 930), Chlofentezine,
Cyclopropancarbonsäure(2-naphthylmethyl)ester (Ro 12-0470), Cyromacin, DDT, Dicofol, N-(3,5-Dichlor-4-(1,1,2,2-tetrafiuoroethoxy)- phenylamino)carbonyl)-2,6-difiuor-ben∑S:τιide (XRD 473), Diflubenzuron, N- (2,3-Dihydro-3-methyl-1,2-thiazol-2-ylidene)-2,4-xyfidine, Dinobuton, Dinocap. Endosulfan, Fenoxycarb, Fenthiocarb, Flubenzimine, Flufenoxuron, Gamma- HCH, Hexythiazox, Hydramethylnon (AC 217 300), Ivermectin, 2-Nitromethyl- 4,5-dihydro-6H-thiazin (SD 52618), 2-Nitromethyl-3,4-dihydrothiazol (SD 35651), 2-Nitromethylene-1,3-thiazinan-3-yl-carbamaldehyde (WL 108 471), Propargite, Teflubenzuron, Tetradifon, Tetrasul, Thiocyclam, Triflumaron, Kernpolyeder- und Granuloseviren.  Cyclopropanecarboxylic acid (2-naphthylmethyl) ester (Ro 12-0470), cyromacin, DDT, dicofol, N- (3,5-dichloro-4- (1,1,2,2-tetrafiuoroethoxy) - phenylamino) carbonyl) -2, 6-difiuor-ben∑S: τιide (XRD 473), diflubenzuron, N- (2,3-dihydro-3-methyl-1,2-thiazol-2-ylidenes) -2,4-xyfidine, dinobutone, dinocap. Endosulfan, fenoxycarb, fenthiocarb, flubenzimine, flufenoxuron, gamma- HCH, hexythiazox, hydramethylnon (AC 217 300), ivermectin, 2-nitromethyl-4,5-dihydro-6H-thiazine (SD 52618), 2-nitromethyl-3,4 -dihydrothiazole (SD 35651), 2-nitromethylene-1,3-thiazinan-3-yl-carbamaldehyde (WL 108 471), propargite, teflubenzuron, tetradifon, tetrasul, thiocyclam, triflumarone, nuclear polyhedron and granulosic viruses.
Der Wirkstoffgehalt der aus den handelsüblichen Formulierungen bereiteten The active substance content of those prepared from the commercially available formulations
Anwendungsformen kann in weiten Bereichen variieren, die Application forms can vary widely
Wirkstoff konzentrationen der Anwendungsformen kann von 0,0001 bis zu 100 Gew.-% Wirkstoff, vorzugsweise zwischen 0,0001 bis 1 Gew.-% liegen. Die Anwendung geschieht in einer den Anwendungsformen angepaßten üblichen Weisen. Active ingredient concentrations of the use forms can be from 0.0001 to 100% by weight of active ingredient, preferably between 0.0001 to 1% by weight. The Application takes place in a customary manner adapted to the application forms.
Nachfolgende Beispiele dienen zur Erläuterung der Erfindung. The following examples serve to explain the invention.
A. Formulierungsbeispiele a) Ein Stäubemittel wird erhalten, indem man 10 Gew.-Teile Wirkstoff und 90 Gew.-Teile Talkum als Inertstoff mischt und in einer Schlagmühle zerkleinert. b) ein in Wasser leicht dispergierbares, benetzbares Pulver wird erhalten, indem man 25 Gew.-Teile Wirkstoff, 65 Gew.-Teile kaolinhaltigen Quarz als A. Formulation Examples a) A dusting agent is obtained by mixing 10 parts by weight of active compound and 90 parts by weight of talc as an inert substance and comminuting them in a hammer mill. b) a wettable powder which is readily dispersible in water is obtained by adding 25 parts by weight of active compound, 65 parts by weight of kaolin-containing quartz as
Inertstoff, 10 Gew.-Teile ligninsulfonsaures Kalium und 1 Gew.-Teil oleoylmethyltaurinsaures Natrium als Netz- und Dispergiermittel mischt und in einer Stiftmühle mahlt. c) Ein in Wasser leicht dispergierbares Dispersionskonzentrat stellt man her, indem man 40 Gew.-Teile Wirkstoff mit 1 Gew.-Teil eines  Inert substance, 10 parts by weight of lignosulfonic acid potassium and 1 part by weight of oleoylmethyl tauric acid sodium as wetting and dispersing agent and mixed in a pin mill. c) A dispersion concentrate which is easily dispersible in water is prepared by mixing 40 parts by weight of active compound with 1 part by weight of a
Sulfobemsteinsäurehalbesters, 2-Gew.-Teilen eines Ligninsulfonsäure- Natriumsalzes und 51 Gew.-Teilen Wasser mischt und in einer  Sulfosuccinic acid half ester, 2 parts by weight of a lignosulfonic acid sodium salt and 51 parts by weight of water and mixed in one
Reibkugelmühle auf eine Feinheit von unter 5 Mikron vermahlt. d) Ein emulgierbares Konzentrat läßt sich herstellen aus 15 Gew.-Teilen  Grinding ball mill ground to a fineness of less than 5 microns. d) An emulsifiable concentrate can be prepared from 15 parts by weight
Wirkstoff, 75 Gew.-Teilen Cyclohexanon als Lösungsmittel und 10 Gew.- Teilen oxethyliertem Nonylphenol (10 AeO) als Emulgator. e) Ein Granulat läßt sich herstellen aus 2 bis 15 Gew.-Teilen Wirkstoff und  Active ingredient, 75 parts by weight of cyclohexanone as a solvent and 10 parts by weight of oxyethylated nonylphenol (10 AeO) as an emulsifier. e) Granules can be produced from 2 to 15 parts by weight of active ingredient and
einem inerten Granulatträgermaterial wie Attapulgit, Bimsgranulat und/oder Quarzsand. Zweckmäßigerweise verwendet man eine Suspension des Spritzpulvers aus Beispiel b) mit einem Feststoffanteil von 30 % und spritzt diese auf die Oberfläche eines Attapulgitgranulats, trocknet und vermischt innig. Dabei beträgt der Gewichtsanteil des Spritzpulvers ca. 5 % und der des inerten Trägermaterials ca. 95 % des fertigen Granulats. an inert granule carrier material such as attapulgite, pumice granulate and / or quartz sand. A suspension of the wettable powder from example b) having a solids content of 30% is expediently used and sprayed onto the surface of an attapulgite granulate, dried and mixed intimately. The proportion by weight of the wettable powder is about 5% and of the inert carrier material approx. 95% of the finished granulate.
B. Chemische Beispiele  B. Chemical examples
Beispiel 7 der Tabelle I n-Propylsulfonylcyanid Example 7 of Table I n-propylsulfonyl cyanide
Zu einer Lösung von 56,4 g (0,447 mol) Na2SO3 und 75,1 g (0,894 mol) NaHCO3 in 1000 ml Wasser werden bei 20 °C 63,7 g (0,447 mol) n-Propylsulfochlorid getropft. Nachdem eine klare Lösung entstanden ist werden bei 0 - 5°C 55 g (0,894 mol) flüssiges LiCN schnell zugetropft und anschließend bei 20 °C 1 Stunde gerührt. Nach Extraktion mit CH2CI2, Eindampfen und Destillation erhält man 51,1 g farbloses Öl vom Kp. 135°C/10 Torr, n22 D = 1,4282 63.7 g (0.447 mol) of n-propyl sulfochloride are added dropwise at 20 ° C. to a solution of 56.4 g (0.447 mol) of Na 2 SO 3 and 75.1 g (0.894 mol) of NaHCO 3 in 1000 ml of water. After a clear solution has formed, 55 g (0.894 mol) of liquid LiCN are quickly added dropwise at 0-5 ° C. and then stirred at 20 ° C. for 1 hour. After extraction with CH 2 Cl 2 , evaporation and distillation, 51.1 g of colorless oil with a bp. 135 ° C./10 Torr, n 22 D = 1.4282
Beispiel 55 der Tabelle I Example 55 of Table I.
N-3,4-Dichlorphenyl-methylsulfonyIformamidrazon N-3,4-dichlorophenylmethylsulfonyformamidrazone
Zu einer Lösung von 5 g (0,048 mol) Methylsulfonylcyanid und 12,5 g (0,048 mol)To a solution of 5 g (0.048 mol) of methylsulfonyl cyanide and 12.5 g (0.048 mol)
3,4-Dichlorphenylhydrazinhydrochlorid in 80 ml MeOH wurden unter Eiskühlung 4,2 g (0,05 mol) NaHCO3 zugegeben. Nach Beenden der Gasentwicklung wird auf3,4-dichlorophenylhydrazine hydrochloride in 80 ml MeOH were added 4.2 g (0.05 mol) NaHCO 3 with ice cooling. After the gas evolution has ended,
Eiswaser gegeben und abgesaugt und anschließend durch Rühren mit n-Heptan gereinigt. Ice water added and suction filtered and then cleaned by stirring with n-heptane.
Ausbeute: 9,9 g vom Schmp.: 149-151 °C (Zers.)  Yield: 9.9 g of mp: 149-151 ° C (dec.)
Beispiel 28 der Tabelle I Example 28 of Table I.
N-3-Chlorbenzoyl-tosylformamidrazon N-3-chlorobenzoyl tosylformamidrazone
Zu einer Lösung von 5 g (0,028 mol) Tosylcyanid in 50 ml MeOH tropft man bei 0°C 4,8 g (0,028 mol) 3-Chlorbenzoylhydrazid in 15 ml MeOH zu. Nach 2 Stunden Rühren bei 20 °C gibt man die Lösung auf Eiswasser, saugt ab und rührt zur Reinigung mit n-Heptan. 4.8 g (0.028 mol) of 3-chlorobenzoyl hydrazide in 15 ml of MeOH are added dropwise to a solution of 5 g (0.028 mol) of tosyl cyanide in 50 ml of MeOH. After stirring for 2 hours at 20 ° C., the solution is poured onto ice water, suction filtered and stirred Cleaning with n-heptane.
Ausbeute: 6,0 g vom Schmp.: 202-204 °C (Zers.)  Yield: 6.0 g of mp: 202-204 ° C (dec.)
In analoger Weise wurden die in der folgenden Tabelle I definierten Verbindungen der Formeln (I) und (II) (siehe Seite 1) erhalten. The compounds of the formulas (I) and (II) (see page 1) defined in Table I below were obtained in an analogous manner.
C) Biologische Beispiele C) Biological examples
Beispiel 1 example 1
Etwa 5 Wochen alte Reispflanzen der Sorte "Ballila" wurden mit den unten angegebenen Konzentrationen der erfindungsgemäßen Verbindungen behandelt. Nach Antrocknen des Spritzbelages wurden die Pflanzen mit einer Rice plants of the "Ballila" variety, about 5 weeks old, were treated with the concentrations of the compounds according to the invention given below. After the spray coating had dried on, the plants were washed with a
Sporensuspension von Pyricularia oryzae gleichmäßig inokuliert und 48 Stunden in eine dunkel gehaltene Klimakammer mit einer Temperatur von 25 °C und 100 % rel. Luftfeuchte gestellt. Danach wurden die Reispflanzen in einem Gewächshaus mit einer Temperatur von 25°C und 80 % rel. Luftfeuchte weiter kultiviert. Nach 5 Tagen erfolgte die Befallsauswertung. Der-Befallsgrad wurde in befallener  Spore suspension of Pyricularia oryzae evenly inoculated and 48 hours in a dark climate chamber with a temperature of 25 ° C and 100% rel. Humidity set. Then the rice plants were in a greenhouse with a temperature of 25 ° C and 80% rel. Humidity further cultivated. The infestation was evaluated after 5 days. The degree of infestation became infested
Blattfläche im Vergleich zu unbehandelten, infizierten Kontrollpflanzen ausgedrückt. Die Ergebnisse sind in Tabelle II zusammengestellt. Leaf area expressed in comparison to untreated, infected control plants. The results are summarized in Table II.
Beispiel 2 Example 2
Tomatenpflanzen der Sorte "Rheinlands Ruhm" wurden im 3 - 4 Blattstadium mit wäßrigen Suspensionen der erfindungsgemäßen Verbindungen gleichmäßig tropfnaß benetzt. Tomato plants of the "Rheinlands Ruhm" variety were uniformly wetted to the wet with 3 to 4 leaf stages with aqueous suspensions of the compounds according to the invention.
Nach dem Antrocknen wurden die Pflanzen mit einer Zoosporangien-Suspension von Phytophthora infestans inokuliert und für 2 Tage unter optimalen After drying, the plants were inoculated with a zoosporangia suspension of Phytophthora infestans and kept under optimal conditions for 2 days
Infektionsbedingungen in einer Klimakammer gehalten. Danach wurden die Pflanzen bis zur Symptomausprägung im Gewächshaus weiter kultiviert. Die Befallsbonitur erfolgte ca. 1 Woche nach Inokulation. Der Befallsgrad der Pflanzen wurde in befallener Blattfläche, bezogen auf unbehandelte infizierte Pflanzen ausgedrückt und ist in Tabelle III wiedergegeben. Infection conditions kept in a climatic chamber. The plants were then cultivated further in the greenhouse until the symptoms developed. The infection was assessed approximately 1 week after inoculation. The degree of infection of the plants was expressed in the infected leaf area, based on untreated infected plants, and is shown in Table III.
Beispiel 3  Example 3
Weinsämlinge der Sorten "Riesling/Ehrenfelder" wurden ca. 6 Wochen nach der Aussaat mit wäßrigen Suspensionen der erfindungsgemäßen Verbindungen tropfnaß behandelt. Nach dem Antrocknen des Spritzbelages wurden die Pflanzen mit einer Zoosporangien-Suspension von Plasmopara viticola inokuliert und tropfnaß in eine Klimakammer mit 23 °C und 80 - 90 % rel. Luftfeuchte gestellt. Wine seedlings of the "Riesling / Ehrenfelder" varieties were treated to runoff with aqueous suspensions of the compounds according to the invention about 6 weeks after sowing. After the spray coating had dried on, the plants were inoculated with a zoosporangia suspension of Plasmopara viticola and dripping wet in a climatic chamber at 23 ° C. and 80-90% rel. Humidity set.
Nach einer Inkubationszeit von 7 Tagen wurden die Pflanzen nochmals über Nacht in die Klimakammer gestellt, um die Sporulation des Pilzes anzuregen. After an incubation period of 7 days, the plants were again placed in the climatic chamber overnight in order to stimulate the sporulation of the fungus.
Anschließend erfolgte die Befallsauswertung. Der Befallsgrad wurde in befallener Blattfläche im Vergleich zu den unbehandelten, infizierten Kontrollpflanzen ausgedrückt und ist in Tabelle IV wiedergegeben. The infestation was then assessed. The degree of infestation was expressed in the infested leaf area in comparison to the untreated, infected control plants and is shown in Table IV.

Claims

Patentansprüche. Claims.
1. Sulfonylformamidrazone der allgemeinen Formel (I) und deren Tautomere der Formel (II) 1. sulfonylformamide zone of the general formula (I) and its tautomers of the formula (II)
worin wherein
R1 = Alkyl, Alkenyl, Alkinyl, Cycloalkyl, Cycloalkenyl, wobei die 5 Gruppen unabhängig voneinander unsubstituiert oder ein- oder mehrfach durch die Reste Halogen, Cyano, Nitro, Mono- und Dialkylamino, Alkoxy, Alkenyloxy, Alkinyloxy, Alkylthio, Alkenylthio, Alkinylthio substituiert sein können oder einen Rest der Formel R 1 = alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, the 5 groups independently of one another unsubstituted or one or more times by the radicals halogen, cyano, nitro, mono- and dialkylamino, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynylthio may be substituted or a radical of the formula
R2 = Alkyl, Alkenyl, Alkinyl, Phenyl und Benzyl, wobei die 5 Gruppen R 2 = alkyl, alkenyl, alkynyl, phenyl and benzyl, the 5 groups
unabhängig voneinander unsubstituiert oder ein- oder mehrfach durch die Reste Halogen, Cyano, Nitro, Mono- und Dialkylamino, Alkoxy, Haloalkyl substituiert sein können oder einen Rest der Formel  independently of one another unsubstituted or substituted one or more times by the radicals halogen, cyano, nitro, mono- and dialkylamino, alkoxy, haloalkyl or a radical of the formula
-C(O)R2', -SO2R2', worin -C (O) R 2 ' , -SO 2 R 2' , wherein
R2' = Alkyl, Alkenyl, Alkinyl, Phenyl und Benzyl, wobei die 5 Gruppen R 2 ' = alkyl, alkenyl, alkynyl, phenyl and benzyl, the 5 groups
unabhängig voneinander unsubstituiert oder ein- oder mehrfach durch die Reste Halogen, Cyano, Nitro, Mono- und Dialkylamino, Alkoxy, Haloalkyl substituiert sein können, bedeutet, n = eine ganze Zahl von 0 - 5, independently of one another can be unsubstituted or substituted one or more times by the radicals halogen, cyano, nitro, mono- and dialkylamino, alkoxy, haloalkyl, n = an integer from 0 to 5,
A = eine direkte Bindung, gesättigte oder ungesättigte, verzweigte oder unverzweigte Alkylkette,  A = a direct bond, saturated or unsaturated, branched or unbranched alkyl chain,
Z = Wasserstoff, Halogen, Nitro, Cyano, Alkyl, Alkenyl, Alkinyl, Cycloalkyl,Z = hydrogen, halogen, nitro, cyano, alkyl, alkenyl, alkynyl, cycloalkyl,
Cycloalkenyl, Alkoxy, Alkenyloxy, Alkinyloxy, Phenyl, Phenoxy,Cycloalkenyl, alkoxy, alkenyloxy, alkynyloxy, phenyl, phenoxy,
Haloalkyl, Haloalkoxy, Alkylthio, Haloalkylthio oder einen Rest derHaloalkyl, haloalkoxy, alkylthio, haloalkylthio or a residue of
Formel formula
-A-NR3 2 bedeuten, worin -A-NR 3 2 , wherein
R3 = unabhängig voneinander Alkyl, Alkenyl, Alkinyl, Cycloalkyl, Phenyl, Benzyl, Alkoxy, Alkenyloxy, Alkinyloxy, Phenyloxy, Benzyloxy, R 3 = independently of one another alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, benzyl, alkoxy, alkenyloxy, alkynyloxy, phenyloxy, benzyloxy,
Alkoxyalkyl, Alkylthioalkyl, Haloalkoxyalkyl, Haloalkylthioalkyl,  Alkoxyalkyl, alkylthioalkyl, haloalkoxyalkyl, haloalkylthioalkyl,
Haloalkyl, Wasserstoff oder einen Rest der Formel  Haloalkyl, hydrogen or a radical of the formula
-C(O)R4, -SO2R4, -SOR4, SR4 oder -C (O) R 4 , -SO 2 R 4 , -SOR 4 , SR 4 or
NR3 2 = Morpholino, Dialkyimorpholino, Piperidino, Piperazino, NR 3 2 = morpholino, dialkyimorpholino, piperidino, piperazino,
Hydrazino, Hydroxylamino, Phthalimido, Maleinimido,  Hydrazino, hydroxylamino, phthalimido, maleinimido,
Dihydrophthalimido  Dihydrophthalimido
oder einen Rest der Formel  or a residue of the formula
-A-C(O)R4 bedeutet, worin -AC (O) R 4 means in which
R4 = Wasserstoff, Alkyl, Alkenyl, Alkinyl, Cycloalkyl, Phenyl, Phenoxy, R 4 = hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, phenoxy,
Phenylthio, OH, SH, Alkoxy, Alkenyloxy, Alkinyloxy, Alkylthio,  Phenylthio, OH, SH, alkoxy, alkenyloxy, alkynyloxy, alkylthio,
Alkenylthio, Alkinylthio, Cycloalkylthio, Cycloalkoxy, Haloalkoxy, Haloalkylthio, Alkoxyalkyl, Alkylthioalkyl oder  Alkenylthio, alkynylthio, cycloalkylthio, cycloalkoxy, haloalkoxy, haloalkylthio, alkoxyalkyl, alkylthioalkyl or
-NR5 2 bedeutet, worin -NR 5 2 means in which
R5 = unabhängig voneinander Alkyl, Alkenyl, Alkinyl, Cycloalkyl, Phenyl, Benzyl, Wasserstoff, Alkoxyalkyl, Alkylthioalkyl oder R 5 = independently of one another alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, Benzyl, hydrogen, alkoxyalkyl, alkylthioalkyl or
NR5 2 = Piperidino, Morpholino, Piperazino, Hydrazino oder NR 5 2 = piperidino, morpholino, piperazino, hydrazino or
Hydroxylamino  Hydroxylamino
oder einen Rest der Formel  or a residue of the formula
-A-SO2R4, -A-SOR4, -A-SR4, -A-P(O)R4 2 bedeutet. -A-SO 2 R 4 , -A-SOR 4 , -A-SR 4 , -AP (O) R 4 2 means.
Verbindungen der Formeln (I) und (II) gemäß Anspruch 1 , dadurch Compounds of formulas (I) and (II) according to claim 1, characterized
gekennzeichnet, daß  characterized in that
R1 = (C1-C6)-Alkyl, (C2-C4)-Alkenyl, (C2-C4)-Alkinyl, (C3-C6)-Cycloalkyl, (C3- C6)-Cycloalkenyl, wobei die 5 Gruppen unabhängig voneinander unsubstituiert oder ein- oder mehrfach durch die Reste Halogen, Cyano, Nitro, Mono- und Di-(C1-C6)-alkylamino, (C1-C4)-Alkoxy, (C2- C4)-AIkenyloxy, (C2-C4)-Alkinyloxy, (C1-C4)-Alkylthio, (C2-C4)-Alkenylthio, (C2-C4)-Alkinylthio substituiert sein können oder einen Rest der Forme! R 1 = (C 1 -C 6 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, (C 3 -C 6 ) cycloalkyl, (C 3 - C 6 ) -Cycloalkenyl, where the 5 groups are independently unsubstituted or one or more times by the radicals halogen, cyano, nitro, mono- and di- (C 1 -C 6 ) alkylamino, (C 1 -C 4 ) alkoxy, ( be C 4) -AIkenyloxy, (C 2 -C 4) alkynyloxy, (C 1 -C 4) alkylthio, (C 2 -C 4) -alkenylthio, (C 2 -C 4 substituted) alkynylthio - C 2 can or a rest of the shapes!
R2 = (C1-C6)-Alkyl, (C2-C4)-Alkenyl, (C2-C4)-Alkinyl, Phenyl und Benzyl, wobei die 5 Gruppen unabhängig voneinander unsubstituiert oder ein- oder mehrfach durch die Reste Halogen, Cyano, Nitro, Mono- und Di-(C1- C4)-alkylamino, (C1-C4)-Alkoxy, Halo-(C1-C4)-alkyl substituiert sein können oder einen Rest der Formel R 2 = (C 1 -C 6 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, phenyl and benzyl, the 5 groups being independently unsubstituted or one or more times by the radicals halogen, cyano, nitro, mono- and di- (C 1 - C 4) alkylamino, (C 1 -C 4) -alkoxy, halo- (C 1 -C 4) alkyl may be substituted or a radical of the formula
-C(O)R2', -SO2R2', worin -C (O) R 2 ' , -SO 2 R 2' , wherein
R2' = (C1-C6)-Alkyl, (C2-C4)-Alkenyl, (C2-C4)-AIkinyI, Phenyl und Benzyl, wobei die 5 Gruppen unabhängig voneinander unsubstituiert oder ein- oder mehrfach durch die Reste Halogen, Cyano, Nitro, Mono- und Di-(C1- C4)-alkylamino, (C1-C4)-Alkoxy, Halo-(C1-C4)-alkyl substituiert sein können, bedeutet, R 2 ' = (C 1 -C 6 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, phenyl and benzyl, the 5 groups being independently unsubstituted or one or more times be - (C 4 C 1) alkylamino, (C 1 -C 4) -alkoxy, halo- (C 1 -C 4) alkyl substituted by the groups halogen, cyano, nitro, mono- and di- can means
n = eine ganze Zahl von 0 - 5, n = an integer from 0 to 5,
A = eine direkte Bindung, gesättigte oder ungesättigte, verzweigte oder unverzweigte Alkylkette,  A = a direct bond, saturated or unsaturated, branched or unbranched alkyl chain,
Z = Wasserstoff, Halogen, Nitro, Cyano, (C1-C6)-Alkyl, (C2-C4)-Alkenyl, (C2- C4)-Alkinyl, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkenyl, (C1-C4)-Alkoxy, (C2-C4)-Alkenyloxy, (C2-C4)-Alkinyloxy, Phenyl, Phenoxy, Halo-(C1-C4)- alkyl, Halo-(C1-C4)-alkoxy, (C1-C4)-Alkylthio, Halo-(C1-C6)-alkylthio oder einen Rest der Formel Z = hydrogen, halogen, nitro, cyano, (C 1 -C 6 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 - C 4 ) alkynyl, (C 3 -C 6 ) cycloalkyl, (C 3 -C 6 ) cycloalkenyl, (C 1 -C 4 ) alkoxy, (C 2 -C 4 ) alkenyloxy, (C 2 -C 4 ) alkynyloxy, phenyl, phenoxy, halo (C 1 - C 4 ) alkyl, halo (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, halo (C 1 -C 6 ) alkylthio or a radical of the formula
-A-NR3 2 bedeuten, worin -A-NR 3 2 , wherein
R3 = unabhängig voneinander (C1-C6)-Alkyl, (C2-C4)-Alkenyl, (C2-C4)-Alkinyl, (C3-C6)-Cycloalkyl, Phenyl, Benzyl, (C1-C4)-Alkoxy, (C2-C4)-Alkenyloxy, (C2-C4)-Alkinyloxy, Phenyloxy, Benzyioxy, (C1-C4)-Alkoxy-(C1-C4)-alkyl, (C1-C4)-Alkylthio-(C1-C4)-alkyl, Halo-(C1-C4)-alkoxy-(C1-C4)-alkyl, Halo- (C1-C4)-alkylthio-(C1-C4)-alkyl, Halo-(C1-C4)-alkyl, Wasserstoff oder einen Rest der Formel R 3 = independently of one another (C 1 -C 6 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, (C 3 -C 6 ) cycloalkyl, phenyl, benzyl, ( C 1 -C 4 ) alkoxy, (C 2 -C 4 ) alkenyloxy, (C 2 -C 4 ) alkynyloxy, phenyloxy, benzyioxy, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkylthio- (C 1 -C 4 ) -alkyl, halo- (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl, halo- (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkyl, halo (C 1 -C 4 ) alkyl, hydrogen or a radical of the formula
-C(O)R4, -SO2R4, -SOR4, SR4 oder -C (O) R 4 , -SO 2 R 4 , -SOR 4 , SR 4 or
NR3 2 = Morpholino, Dialkylmorpholino, Piperidino, Piperazino, NR 3 2 = morpholino, dialkylmorpholino, piperidino, piperazino,
Hydrazino, Hydroxylamino, Phthalimido, Maleinimido,  Hydrazino, hydroxylamino, phthalimido, maleinimido,
Dihydrophthalimido  Dihydrophthalimido
oder einen Rest der Formel  or a residue of the formula
-A-C(O)R4 bedeutet, worin -AC (O) R 4 means in which
R4 = Wasserstoff, (C1-C6)-Alkyl, (C2-C4)-Alkenyl, (C2-C4)-Alkinyl, (C3-C6)-R 4 = hydrogen, (C 1 -C 6 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, (C 3 -C 6 ) -
Cyclöalkyl, Phenyl, Phenoxy, Phenylthio, OH, SH, (C1-C4)-Alkoxy, (C2- C4)-Alkyloxy, (C2-C4)-Alkinyloxy, (C1-C4)-Alkylthio, (C2-C4)-Alkenylthio, (C2-C4)-Alkinylthio, (C3-C6)-Cycloalkylthio, (C3-C6)-Cycloalkyloxy, Halo- R5 = unabhängig voneinander (C1-C6)-Alkyl, (C2-C4)-Alkenyl, (C2-C4)-Alkϊnyl, (C3-C6)-Cycloalkyl, Phenyl, Benzyl, Wasserstoff, (Ca-CJ-Alkoxy-(C1-C4)- alkyl, (C1-C4)Alkylthio-(C1-C4)-alkyl oder Cycloalkyl, phenyl, phenoxy, phenylthio, OH, SH, (C 1 -C 4 ) alkoxy, (C 2 - C 4 ) alkyloxy, (C 2 -C 4 ) alkynyloxy, (C 1 -C 4 ) - Alkylthio, (C 2 -C 4 ) alkenylthio, (C 2 -C 4 ) alkynylthio, (C 3 -C 6 ) cycloalkylthio, (C 3 -C 6 ) cycloalkyloxy, halo- R 5 = independently of one another (C 1 -C 6 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, (C 3 -C 6 ) cycloalkyl, phenyl, benzyl, hydrogen , (Ca-CJ-alkoxy- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkyl or
NR5 2 = Piperidino, Morpholino, Piperazino, Hydrazino oder NR 5 2 = piperidino, morpholino, piperazino, hydrazino or
Hydroxylamino  Hydroxylamino
oder einen Rest der Formel  or a residue of the formula
-A-SO2R4, -A-SOR4, -A-SR4, -A-P(O)R4 2 bedeutet. -A-SO 2 R 4 , -A-SOR 4 , -A-SR 4 , -AP (O) R 4 2 means.
3. Verfahren zur Herstellung von Verbindungen der Formeln (I) und (II) gemäß Anspruch 1 oder 2, dadurch gekennzeichnet, daß eine Verbindung der Formel (III) 3. A process for the preparation of compounds of the formulas (I) and (II) according to claim 1 or 2, characterized in that a compound of the formula (III)
R1 - SO2 - CN (III), worin R1 die unter den Formeln (I) und (II) genannte Bedeutung besitzt, mit einer Verbindung der Formel (IV) R 1 - SO 2 - CN (III), in which R 1 has the meaning given under the formulas (I) and (II), with a compound of the formula (IV)
R2 - NH - NH2 (IV), worin R2 die unter den Formeln (I) und (II) beschriebene Bedeutung hat, oder eines Salzes dieser Verbindung, in Gegenwart einer geeigneten Base, in einem polaren Lösungsmittel umgesetzt wird. R 2 - NH - NH 2 (IV), wherein R 2 has the meaning described under the formulas (I) and (II), or a salt of this compound, in the presence of a suitable base, in a polar solvent.
4. Schädlingsbekämpfungsmittel, dadurch gekennzeichent, daß sie eine 4. Pesticides, characterized in that they have a
wirksame Menge einer Verbindung der Formel I oder II gemäß Anspruch 1 oder 2 und die üblichen Formulierungshilfsmittel enthalten.  effective amount of a compound of formula I or II according to claim 1 or 2 and the usual formulation auxiliaries.
5. Fungizide Mittel, dadurch gekennzeichent, daß sie eine wirksame Menge 5. Fungicidal agents, characterized in that they are an effective amount
einer Verbindung der Formel I oder II gemäß Anspruch 1 oder 2 und die üblichen Formulierungshilfsmittel enthalten. Fungizide Mittel, dadurch gekennzeichent, daß sie eine wirksame Menge einer Verbindung der Formel I oder II gemäß Anspruch 1 oder 2 und die üblichen Formulierungshilfsmittel enthalten. a compound of formula I or II according to claim 1 or 2 and the usual formulation auxiliaries. Fungicidal compositions, characterized in that they contain an effective amount of a compound of formula I or II according to claim 1 or 2 and the usual formulation auxiliaries.
Verwendung von Verbindungen der Formel I oder II gemäß Anspruch 1 oder 2 zur Bekämpfung von Pflanzenschädlingen. Use of compounds of formula I or II according to claim 1 or 2 for controlling plant pests.
Verwendung von Verbindungen der Formel I oder II gemäß Anspruch 1 oder 2 zur Bekämpfung von Schadpilzen. Use of compounds of formula I or II according to claim 1 or 2 for combating harmful fungi.
Verfahren zur Bekämpfung von Pflanzenschädlingen, dadurch Process for controlling plant pests, thereby
gekennzeichnet, daß man auf diese oder die von ihnen befallenen Pflanzen, Flächen oder Substrate eine wirksame Menge einer Verbindung der Formel I oder II gemäß Anspruch 1 oder 2 appliziert. characterized in that an effective amount of a compound of formula I or II according to claim 1 or 2 is applied to these or the plants, areas or substrates affected by them.
Verfahren zur Bekämpung von Schadpilzen, dadurch gekennzeichnet, daß man auf diese oder die von ihnen befallenen Pflanzen, Flächen oder Process for controlling harmful fungi, characterized in that one or on these or the plants, areas or plants infested by them
Substrate eine wirksame Menge einer Verbindung der Formel I oder II gemäß Anspruch 1 oder 2 appliziert. Substrates applied an effective amount of a compound of formula I or II according to claim 1 or 2.
EP92911540A 1991-06-08 1992-06-04 Sulphonyl formamidrazones, methods of preparing them, agents containing them, and their use against plant pests Withdrawn EP0589932A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4118942 1991-06-08
DE4118942 1991-06-08
PCT/EP1992/001245 WO1992022526A1 (en) 1991-06-08 1992-06-04 Sulphonyl formamidrazones, methods of preparing them, agents containing them, and their use against plant pests

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EP92109469A Withdrawn EP0518215A1 (en) 1991-06-08 1992-06-04 Sulfonylformamidrazones, process for their preparation, medium containing them, and their use as herbicides

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Publication number Priority date Publication date Assignee Title
CA994346A (en) * 1971-10-19 1976-08-03 Uwe D. Treuner 3-arylsulfonyl-1,2,4-oxadiazoles
US3755306A (en) * 1972-09-05 1973-08-28 Squibb & Sons Inc 3-arylsulfony l-1,2,4-oxadiazoles

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9222526A1 *

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