EP0589932A1 - Sulfonylformamidrazones, leur procede de fabrication, agents les renfermant et leur utilisation pour la destruction des parasites vegetaux - Google Patents

Sulfonylformamidrazones, leur procede de fabrication, agents les renfermant et leur utilisation pour la destruction des parasites vegetaux

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Withdrawn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)
English (en)
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/fr
Withdrawn legal-status Critical Current

Links

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.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (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.
EP92911540A 1991-06-08 1992-06-04 Sulfonylformamidrazones, leur procede de fabrication, agents les renfermant et leur utilisation pour la destruction des parasites vegetaux Withdrawn EP0589932A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4118942 1991-06-08
DE4118942 1991-06-08
PCT/EP1992/001245 WO1992022526A1 (fr) 1991-06-08 1992-06-04 Sulfonylformamidrazones, leur procede de fabrication, agents les renfermant et leur utilisation pour la destruction des parasites vegetaux

Publications (1)

Publication Number Publication Date
EP0589932A1 true EP0589932A1 (fr) 1994-04-06

Family

ID=6433534

Family Applications (2)

Application Number Title Priority Date Filing Date
EP92109469A Withdrawn EP0518215A1 (fr) 1991-06-08 1992-06-04 Sulfonylformamidrazones, procédé pour leur préparation, moyen les contenant et leur emploi comme herbicides
EP92911540A Withdrawn EP0589932A1 (fr) 1991-06-08 1992-06-04 Sulfonylformamidrazones, leur procede de fabrication, agents les renfermant et leur utilisation pour la destruction des parasites vegetaux

Family Applications Before (1)

Application Number Title Priority Date Filing Date
EP92109469A Withdrawn EP0518215A1 (fr) 1991-06-08 1992-06-04 Sulfonylformamidrazones, procédé pour leur préparation, moyen les contenant et leur emploi comme herbicides

Country Status (5)

Country Link
EP (2) EP0518215A1 (fr)
JP (1) JPH0686420B2 (fr)
AU (1) AU1920792A (fr)
IE (1) IE921836A1 (fr)
WO (1) WO1992022526A1 (fr)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
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 *

Also Published As

Publication number Publication date
AU1920792A (en) 1993-01-12
WO1992022526A1 (fr) 1992-12-23
IE921836A1 (en) 1992-12-16
EP0518215A1 (fr) 1992-12-16
JPH0686420B2 (ja) 1994-11-02
JPH06502656A (ja) 1994-03-24

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