WO1998038172A1 - Derives de phenylaminosulfonyluree en tant que fongicide et pesticide - Google Patents

Derives de phenylaminosulfonyluree en tant que fongicide et pesticide Download PDF

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Publication number
WO1998038172A1
WO1998038172A1 PCT/EP1998/000803 EP9800803W WO9838172A1 WO 1998038172 A1 WO1998038172 A1 WO 1998038172A1 EP 9800803 W EP9800803 W EP 9800803W WO 9838172 A1 WO9838172 A1 WO 9838172A1
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Prior art keywords
carbon atoms
alkyl
spp
halogen
methyl
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PCT/EP1998/000803
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German (de)
English (en)
Inventor
Mark Wilhelm Drewes
Ernst Rudolf Gesing
Johannes Rudolf Jansen
Rolf Kirsten
Klaus-Helmut Müller
Ulrich Philipp
Hans-Jochem Riebel
Klaus Stenzel
Ulrike Wachendorff-Neumann
Christoph Erdelen
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Bayer Aktiengesellschaft
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Priority to JP53723998A priority Critical patent/JP2001513092A/ja
Priority to EP98910654A priority patent/EP0973751A1/fr
Priority to AU64966/98A priority patent/AU6496698A/en
Publication of WO1998038172A1 publication Critical patent/WO1998038172A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D521/00—Heterocyclic compounds containing unspecified hetero rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof

Definitions

  • the invention relates to new phenylaminosulfonylurea derivatives, a process for their preparation and their use as fungicides.
  • Rl for optionally substituted alkyl or a group
  • R * represents hydrogen or optionally substituted alkyl, alkoxy, dialkylarnino, cycloalkyl, cycloalkenyl, phenyl or heterocyclyl.
  • R9 and R * ⁇ each stand for alkyl or together for alkanediyl
  • Rl 1 represents optionally substituted alkyl
  • R ⁇ , R ⁇ and R ⁇ are the same or different and each represents hydrogen, halogen, cyano, nitro, each optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkenyl, alkenyloxy, cycloalkyl or cycloal- are koxy, but one of the radicals R ⁇ , R3 or R4 is different from hydrogen,
  • R5 for halogen, cyano, nitro, each optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkenyl, alkenyloxy, cycloalkyl or
  • R ⁇ and R ⁇ are the same or different and are each for halogen or for alkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, each optionally substituted by halogen or alkoxy,
  • Rl2 represents hydrogen, halogen, cyano or alkyl optionally substituted by halogen or alkoxy
  • the saturated or unsaturated hydrocarbon chains such as alkyl, alkanediyl, alkenyl or alkynyl, are in each case straight-chain or branched, also in combination with heteroatoms, such as in alkoxy, alkylthio or alkylamino.
  • Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
  • Aryl stands for aromatic, mono or polycyclic hydrocarbon rings, such as phenyl, naphthyl, anthranyl, phenanthryl, preferably phenyl or naphthyl, especially phenyl.
  • Heterocyclyl stands for saturated or unsaturated, as well as aromatic, ring-shaped compounds in which at least one ring member is a hetero atom, ie an atom other than carbon. If the ring contains several heteroatoms, these can be the same or different. Heteroatoms are preferably oxygen, nitrogen or sulfur. If appropriate, the ring-shaped compounds together with other carbocyclic or heterocyclic, fused or bridged rings together form a polycyclic ring system. Mono- or bicyclic ring systems are preferred, in particular mono- or bicyclic aromatic ring systems.
  • Cycloalkyl stands for saturated, carbocyclic, ring-shaped compounds which optionally form a polycyclic ring system with other carbocyclic, fused or bridged rings.
  • Cycloalkenyl stands for carbocyclic, ring-shaped compounds which contain at least one double bond and optionally form a polycyclic ring system with other carbocyclic, fused or bridged rings.
  • R6, R ⁇ and G have the meanings given above, with chlorosulfonyl isocyanate, optionally in the presence of a diluent, and the chlorosulfonylureas of the general formula formed
  • R ⁇ , R ⁇ and G have the meanings given above,
  • R, R ⁇ , R3 ; R4 and R ⁇ have the meanings given above,
  • the fused azole derivatives of the formula (I) and their acid addition salts and metal salt complexes have very good microbicidal properties and can be used both in crop protection and in material protection.
  • the invention preferably relates to compounds of the formula (I) in which
  • R ⁇ for hydrogen, for optionally substituted by fluorine, chlorine, bromine, alkoxy having 1 to 3 carbon atoms, alkylthio having 1 to 3 carbon atoms, alkylsulfinyl having 1 to 3 carbon atoms or alkylsulfonyl having 1 to 3 carbon atoms, or dial- kylamino, each with 1 to 6 carbon atoms in the individual alkyl parts, for each optionally by fluorine, chlorine, bromine and / or
  • R9 and RIO each represent alkyl having 1 to 3 carbon atoms or together represent alkanediyl having 1 to 3 carbon atoms
  • Rl ⁇ represents alkyl with 1 to 4 carbon atoms optionally substituted by halogen or phenyl
  • R2, R3 and R ⁇ are the same or different and each represents hydrogen, halogen, cyano, nitro, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4
  • R5 for halogen, cyano, nitro, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, alkylsulfinyl with 1 to 4 carbon atoms, alkylsulfonyl with 1 to 4 carbon atoms, alkenyl with 2 to 4 carbon atoms, Alkenyloxy having 2 to 4 carbon atoms, haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 5 identical or different halogen atoms, cycloalkyl having 3 to 6 carbon atoms or cycloalkoxy having 3 to 6 carbon atoms,
  • R6 and R ⁇ are the same or different and are each for halogen or for alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino or dialkylamino each with 1 to 4 carbon atoms in each individual, optionally substituted by halogen or alkoxy having 1 to 4 carbon atoms Alkyl parts, alkenyl or alkynyl each having 2 to 4 carbon atoms, cycloalkyl having 3 to 6 carbon atoms or heterocyclyloxy having 3 to 6 ring members and 1 to 3 heteroatoms and G represents nitrogen or where
  • Rl2 represents hydrogen, halogen, cyano or alkyl having 1 to 4 carbon atoms optionally substituted by halogen or alkoxy having 1 to 4 carbon atoms.
  • the invention further preferably comprises sodium, potassium, magnesium, calcium, ammonium, C 1 -C 4 alkyl ammonium, di (C 1 -C 4 alkyl) ammonium, tri (C 1 -C 4 alkyl) -ammonium-, C5- or Cg-cycloalkyl-ammonium and di- (C,; - C2-alkyl) -benzyl-ammonium salts of compounds of formula (I), in which R, R ⁇ , R 3 , R4, R5 ⁇ R6 ; R7 un ( j Q ⁇ have the meanings preferably given above.
  • the invention relates in particular to compounds of the formula (I) in which
  • R for methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, n-, i- or s-pentyl or one optionally substituted by fluorine, chlorine, thiomethyl and / or sulfonylmethyl grouping
  • R ⁇ for hydrogen, for methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, n-, i- or s-pentyl, methoxy, ethoxy, each optionally substituted by fluorine and / or chlorine, n- or i-propoxy, dimethylamino, diethylamino, for methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, methylthioethyl, ethylthiomethyl, ethylthioethyl, methylsulfinylmethyl, ethylsulfinylmethyl, methylsulfonylmethyl, ethylsulfonylmethyl or meth for optionally , Chlorine and / or methyl substituted cyclopropyl, cyclopropylmethyl, cyclobuty
  • R9 and R ⁇ each represent methyl, ethyl, n- or i-propyl or together for methylene, 1,1-ethanediyl, 1,2-ethanediyl 1,1-, 1,2-, 1,3- or 2,2 -Pro- pandiyl stand,
  • R represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or benzyl
  • R ⁇ , R3 and R ⁇ are the same or different and each represents hydrogen, fluorine, chlorine, bromine, cyano, nitro, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy,
  • R5 for fluorine, chlorine, bromine, cyano, nitro, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoromethyl, difluoromethylfluifluoromethyl, difluoromethyl, difluoromethyl, difluoromethyl, difluoromethyl, difluoromethyl, difluoromethyl Allyl,
  • R6 and R are the same or different and each represents chlorine, methyl, ethyl, vinyl, allyl, 2-methylethen-l-yl, ethinyl, 2-methylethin-l-yl, propargyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoroethoxy, Methylthio, ethylthio, methylamino, ethylamino, dimethylamino, cyclopropyl or oxethan-1-yloxy and represents nitrogen or where
  • Rl2 represents hydrogen, fluorine, chlorine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, trifluoroethyl, methoxymethyl or ethoxymethyl.
  • radical definitions listed above apply both to the end products of the formula (I) and correspondingly to the starting or intermediate products required in each case for the preparation.
  • the radical definitions specified for these radicals in the respective combinations or preferred combinations of radicals are independently replaced by radical definitions of other preferred ranges, regardless of the combination specified in each case.
  • Formula (II) provides a general definition of the aminotriazines or pyrimidines required to carry out process a) according to the invention for the preparation of the compounds of formula (I) according to the invention.
  • R ⁇ , R ⁇ and G preferably or in particular have those meanings which have already been in connection with the description of the compounds of the invention
  • Formula (I) was given as preferred or as particularly preferred for R, R ⁇ and G.
  • aminotriazines or pyrimidines of the formula (II) are known (compare, for example, EP-A 476554) and can be prepared by known methods.
  • chlorosulfonyl isocyanate also required to carry out the process according to the invention for the preparation of the compounds of the formula (I) is a generally known laboratory chemical.
  • Formula (IV) provides a general definition of the anilines which are further required to carry out the process according to the invention for the preparation of the compounds of the formula (I) according to the invention.
  • R, R ⁇ , R3 ; R4 un (j R5 ) preferably or in particular have those meanings which have already menhang together with the description of the compounds of formula (I) as being preferred or as particularly preferred for R, R ⁇ , R3 R4 un d? Specified R5 .
  • anilines of the formula (IV) are known and / or can be prepared by processes known per se (compare, for example, US Pat. No. 5405998 and DE-A 4414476).
  • diluents Practically all inert organic solvents can be used as diluents. These preferably include aliphatic and aromatic, optionally halogenated hydrocarbons such as pentane, hexane, heptane, cyclohexane, petroleum ether, gasoline, ligroin, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, ethers such as diethyl and dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxane, ketones such as acetone, methyl ethyl, methyl isopropyl and methyl isobutyl ketone, esters such as
  • Acid acceptors which can be used in the process according to the invention are all acid binders which can customarily be used for such reactions.
  • Alkali metal hydroxides such as e.g. Sodium and potassium hydroxide,
  • Alkaline earth hydroxides such as Calcium hydroxide, alkali carbonates and alcoholates such as sodium and potassium carbonate, such as sodium and potassium tert-butoxide, also aliphatic, aromatic or heterocyclic amines, for example triethylamine, trimethylamine, dimethylaniline, dimethylbenzylamine, pyridine, 1,5-diazabicyclo [4 , 3,0] - non-5-ene (DBN), 1,8-diazabicyclo- [5,4,0] -undec-7-ene (DBU) and 1,4-diazabicyclo-
  • DBN 1,5-diazabicyclo [4 , 3,0] - non-5-ene
  • DBU 1,8-diazabicyclo- [5,4,0] -undec-7-ene
  • DBU 1,4-diazabicyclo-
  • reaction temperatures can be varied within a wide range in the process according to the invention. In general, temperatures between -30 ° C and + 80 ° C, preferably at temperatures between -10 ° C and
  • the process according to the invention is generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure.
  • the starting materials required in each case are generally used in approximately equimolar amounts. However, it is also possible to use one of the two components used in each case in a larger excess.
  • the reactions are generally carried out in a suitable diluent in the presence of an acid acceptor, and the reaction mixture is kept at the required temperature for several hours. door stirred.
  • Working up in the process according to the invention is carried out in each case by customary methods (cf. the preparation examples).
  • salts can be prepared from the compounds of the general formula (I) according to the invention.
  • Such salts are obtained in a simple manner by customary salt formation methods, for example by dissolving or dispersing a compound of the formula (I) in a suitable solvent, e.g. Methylene chloride, acetone, tert-butyl methyl ether or toluene, and addition of a suitable base.
  • a suitable solvent e.g. Methylene chloride, acetone, tert-butyl methyl ether or toluene
  • the salts can then be isolated - if necessary after prolonged stirring - by concentrating or suctioning off.
  • the substances according to the invention have a strong microbicidal action and can be used to control unwanted microorganisms, such as fungi and bacteria, in crop protection and in material protection.
  • Fungicides can be used to protect plants against Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
  • Bactericides can be used in plant protection to combat Pseudomonadaceae,
  • pathogens of fungal and bacterial are exemplary but not limiting
  • Xanthomonas species such as, for example, Xanthomonas campestris pv. Oryzae;
  • Pseudomonas species such as, for example, Pseudomonas syringae pv. Lachrymans;
  • Erwinia species such as, for example, Erwinia amylovora;
  • Pythium species such as, for example, Pythium ultimum
  • Phytophthora species such as, for example, Phytophthora infestans
  • Pseudoperonospora species such as, for example, Pseudoperonospora humuli or
  • Plasmopara species such as, for example, Plasmopara viticola
  • Bremia species such as, for example, Bremia lactucae
  • Peronospora species such as, for example, Peronospora pisi or P. brassicae;
  • Erysiphe species such as, for example, Erysiphe graminis
  • Sphaerotheca species such as, for example, Sphaerotheca Faniginea
  • Podosphaera species such as, for example, Podosphaera leucotricha
  • Venturia species such as, for example, Venturia inaequalis
  • Pyrenophora species such as, for example, Pyrenophora teres or P. graminea
  • Drechslera (Conidial form: Drechslera, Syn: Helminthosporium);
  • Cochliobolus species such as, for example, Cochliobolus sativus (conidial form: Drechslera, Syn: Helminthosporium);
  • Uromyces species such as, for example, Uromyces appendiculatus
  • Puccinia species such as, for example, Puccinia recondita
  • Sclerotinia species such as, for example, Sclerotinia sclerotiorum
  • Tilletia species such as, for example, Tilletia caries
  • Ustilago species such as, for example, Ustilago nuda or Ustilago avenae
  • Pellicularia species such as, for example, Pellicularia sasakii;
  • Pyricularia species such as, for example, Pyricularia oryzae
  • Fusarium species such as, for example, Fusarium culmorum
  • Botrytis species such as, for example, Botrytis cinerea; Septoria species, such as, for example, Septoria nodorum;
  • Leptosphaeria species such as, for example, Leptosphaeria nodorum;
  • Cercospora species such as, for example, Cercospora canescens
  • Alternaria species such as, for example, Alternaria brassicae;
  • Pseudocercosporella species such as, for example, Pseudocercosporella he otrichoides.
  • the active compounds according to the invention can be particularly successful
  • the active substances are suitable for combating animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in forests, in the protection of stored goods and materials, and in the hygiene sector. They can preferably be used as pesticides. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the pests mentioned above include:
  • Isopoda e.g. Oniscus asellus, Armadillidium vulgare, Porcellio scaber. From the order of the Diplopoda e.g. Blaniulus guttulatus.
  • Thysanura e.g. Lepisma saccharina.
  • Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci.
  • Conoderus spp. Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica.
  • Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
  • Acarina e.g. Acarus siro, Argas spp., Ornithodoros spp.
  • Plant-parasitic nematodes include e.g. Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp.
  • Pratylenchus spp. Radopholus similis
  • Ditylenchus dipsaci Ditylenchus dipsaci
  • Tylenchulus semipenetrans Heterodera spp.
  • Globodera spp. Meloidogyne spp.
  • Aphelenchoides spp. Longidorus spp.
  • Xiphinema spp. Trichodorus spp.
  • the compounds of the formula (I) according to the invention are notable in particular for their action against insects which damage plants, such as, for example, against the larvae of the horseradish leaf beetle (Phaedon cochleariae) and the onion fly (Hylemyia antiqua).
  • the active ingredients can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, and ULV - Cold and warm fog formulations.
  • formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents, under pressure, AI liquid gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • extenders that is to say liquid solvents, under pressure, AI liquid gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • aromatics such as xylene, toluene or
  • Alkylnaphthalenes chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions, alcohols, such as butanol or glycol, and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, highly polar solvents, such as dimethylformamide and dimethyl sulfoxide, and water.
  • Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and pressure, e.g.
  • Aerosol propellants such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.
  • Possible solid carriers are: e.g. natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates.
  • the following are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and
  • emulsifiers and / or foaming agents are: e.g. nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates.
  • Possible dispersants are: e.g. Lignin liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as cinimiarabicum, polyvinyl alcohol, polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc are used.
  • inorganic pigments e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc are used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be mixed with known fungicides, bactericides, acaricides, nematicides or
  • Insecticides can be used, e.g. to broaden the spectrum of activity or to prevent the development of resistance. In many cases, synergistic effects are obtained, i.e. the effectiveness of the mixture is greater than the effectiveness of the individual components.
  • Debacarb dichlorophene, diclobutrazole, diclofluanide, diclomezin, diclora, diethofencarb, difenoconazole, dimetliirimol, dimethomorph, diniconazole, diniconazole M, Dinocap, Diphenylamine, Dipyrithione, Ditalimfos, Dithianon, Dodemorpn, Dodine, Drazoxolon,
  • Imazalil Imibenconazol, Iminoctadin, Iminoctadinealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazol, Iprobefos (IBP), Iprodione, Irumamycin, Isoprothiolan, Isovaledione,
  • Mancopper Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Meth tartroxam, Metiram, Metomeclam, Metsulfovax,
  • Paclobutrazole peognizolate, penconazole, pencycuron, phosdiphen, pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz, procymidon, propamocarb, propanosine Sodium, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilon, pyroxyfur,
  • Fenamiphos Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil,
  • Fluazinam Fluazuron, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenprox, Fluvalinate, Fonophos, Formothion, Fosthiazat, Fubfenprox, Furathiocarb,
  • Parathion A Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenophos, Promecarb, Propaphos, Propoxur, Prothiophos, Prothoat, Pymethionos, Pyridaphrinophone, Pyridaphrinin, Pyridaphrin Pyrethrum, Pyridaben, Pyrimidifen, Pyriproxifen,
  • Tebufenozide Tebufenpyrad
  • Tebupirimiphos Teflubenzuron
  • Tefluthrin Temephos
  • Terbam Terbufos
  • Tetrachlorvinphos Thiafenox, Thiodicarb, Thiofanox, Thiomethon
  • the active compounds according to the invention can also be used in their commercially available formulations and in the use forms prepared from these formulations
  • Synergists are compounds through which the action of the active ingredients is increased without the added synergist itself having to be active.
  • the active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges.
  • the active substance concentration of the use forms can be from 0.0000001 to 95% by weight of active substance, preferably between 0.0001 and 1% by weight. 15
  • the application takes place in a customary manner adapted to the application forms.
  • Active ingredient characterized by an excellent residual effect on wood and clay as well as a good alkali stability on limed substrates.
  • the active compounds according to the invention act not only against plant, hygiene and stored-product pests, but also in the veterinary sector against animal parasites (ectoparasites) such as tick ticks, leather ticks, mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, hair lice, Featherlings and fleas.
  • animal parasites ectoparasites
  • tick ticks leather ticks
  • mites running mites
  • flies stinging and licking
  • parasitic fly larvae lice, hair lice, Featherlings and fleas.
  • Phlebotomus spp. Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp ., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp.
  • Siphonaptrida for example Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp ..
  • the Heteropterida for example Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp ..
  • Actinedida Prostigmata
  • Acaridida e.g. Acarapis spp., Cheyletiella spp., Ornitrocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp.,
  • Caloglyphus spp. Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp ..
  • the active compounds of the formula (I) according to the invention are also suitable for controlling arthropods which are used in agricultural animals, e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as e.g. Dogs, cats, house birds, aquarium fish and so-called experimental animals, such as Infest hamsters, guinea pigs, rats and mice. By fighting these arthropods, deaths and
  • the active compounds according to the invention are used in the veterinary sector in a known manner by enteral administration in the form of, for example, tablets, capsules, drinkers, drenches, granules, pastes, boluses, the feed-through method, suppositories, by parenteral administration, for example by Injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, by nasal application, by dermal application in the form of, for example, diving or bathing (dipping), spraying (spray), pouring on (pour-on and spot-on), washing, powdering and with the aid of shaped articles containing active ingredients, such as necklaces, ear tags, tail tags, limb tapes, holsters, marking devices, etc.
  • enteral administration in the form of, for example, tablets, capsules, drinkers, drenches, granules, pastes, boluses, the feed-through method, suppositories
  • parenteral administration for example by In
  • Formula (I) as formulations for example powders, emulsions, flowable agents
  • formulations for example powders, emulsions, flowable agents
  • active compounds in an amount of 1 to 80% by weight, directly or after
  • insects may be mentioned by way of example and preferably, but without limitation:
  • Termites like Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucihegus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus.
  • Bristle tails such as Lepisma saccarina.
  • Bacteria, fungi, yeasts, algae and mucilaginous organisms may be mentioned as microorganisms which can cause degradation or a change in the technical materials.
  • the active compounds according to the invention preferably act against fungi, in particular mold, wood-discoloring and wood-destroying fungi
  • microorganisms of the following genera may be mentioned:
  • Alternaria such as Alternaria tenuis, Aspergillus, such as Aspergillus niger,
  • Chaetomium like Chaetomium globosum
  • Coniophora such as Coniophora puetana
  • Lentinus such as Lentinus tigrinus
  • Penicillium such as Penicillium glaucum
  • Polyporus such as Polyporus versicolor
  • Aureobasidium such as Aureobasidium pullulans
  • Sclerophoma such as Sclerophoma pityophila
  • Trichoderma like Trichoderma viride
  • Escherichia such as Escherichia coli
  • Pseudomonas such as Pseudomonas aeruginosa
  • Staphylococcus such as Staphylococcus aureus.
  • non-living materials such as preferably plastics, adhesives, glues, papers and cartons, leather, wood and wood processing products and paints.
  • the material to be protected against insect infestation is very particularly preferably wood and wood processing products.
  • Wood and wood processing products which can be protected by the agent according to the invention or mixtures containing it are to be understood as examples of construction timber, wooden beams, railway sleepers, bridge parts, jetties, wooden vehicles, boxes, pallets, containers, telephone masts, wooden cladding, wooden windows and doors.
  • Plywood, chipboard, carpentry or wood products that are generally used in house construction or joinery
  • the active compounds can be used as such, in the form of concentrates or generally customary formulations such as powders, granules, solutions, suspensions, emulsions or
  • the formulations mentioned can be prepared in a manner known per se, for example by mixing the active ingredients with at least one solvent or diluent, emulsifier, dispersant and / or binder or fixative,
  • Water repellants optionally desiccants and UV stabilizers and optionally dyes and pigments as well as other processing aids
  • the agents or concentrates used to protect wood and wood-based materials contain the active ingredient according to the invention in a concentration of 0.0001 to
  • the amount of the agents or concentrates used depends on the type and occurrence of the insects or microorganisms and on the medium. The optimum amount can be determined by using a series of tests. In general, however, it is sufficient 0.0001 to 20 % By weight, preferably 0.001 to 10% by weight, of the active ingredient, based on the material to be protected
  • An organic-chemical solvent or solvent mixture and / or an oily or oil-like, slightly volatile organic-chemical solvent or solvent mixture and / or a polar solvent serves as the solvent and / or diluent organic chemical solvent or solvent mixture and / or water and optionally an emulsifier and / or wetting agent.
  • the organic chemical solvents used are preferably oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C., preferably above 45 ° C.
  • Corresponding mineral oils or their aromatic fractions or mineral oil-containing solvent mixtures, preferably white spirit, petroleum and / or alkylbenzene, are used as such low-volatility, water-insoluble, oily and oily solvents.
  • Mineral oils with a boiling range of 170 to 220 ° C, white spirit with a boiling range of 170 to 220 ° C, spindle oil with a boiling range of 250 to 350 ° C, petroleum or aromatics with a boiling range of 160 to 280 ° C, turpentine oil and Like. Used.
  • organic low-volatility oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C can be partially replaced by slightly or medium-volatile organic chemical solvents, with the proviso that the solvent mixture also has an evaporation number 35 and a flash point above 30 ° C, preferably above 45 ° C, and that the insecticide-fungicide mixture is soluble or emulsifiable in this solvent mixture.
  • Solvent or solvent mixture or an aliphatic polar organic chemical solvent or solvent mixture replaced.
  • aliphatic organochemical solvents containing hydroxyl and / or ester and / or ether groups such as glycol ethers, esters or the like are used.
  • the organic-chemical binders used are the water-thinnable and / or synthetic resins which are soluble or dispersible or emulsifiable in the organic chemical solvents used and / or binding drying oils, in particular binders consisting of or containing an acrylate resin, a vinyl resin , e.g. Polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene-coumarone resin, silicone resin, drying vegetable and / or drying oils and / or physically drying binders based on a natural and / or synthetic resin used.
  • binders consisting of or containing an acrylate resin, a vinyl resin , e.g. Polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as in
  • the synthetic resin used as a binder can be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances up to 10% by weight can also be used as binders. In addition, known dyes, pigments, water-repellants, odor correctors and inhibitors or anticorrosive agents and the like can be used.
  • At least one alkyd resin or modified alkyd resin and / or a drying vegetable oil is preferably contained in the agent or in the concentrate as the organic chemical binder.
  • Alkyd resins with an oil content of more than 45% by weight, preferably 50 to 68% by weight, are preferably used according to the invention.
  • binder All or part of the binder mentioned can be replaced by a fixing agent (mixture) or a plasticizer (mixture). These additives are intended to prevent volatilization of the active ingredients and crystallization or precipitation. They preferably replace 0.01 to 30% of the binder (based on
  • the plasticizers come from the chemical classes of phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate, phosphoric acid esters such as tributyl phosphate, adipic acid esters such as di- (2-ethylhexyl) adipate, stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, higher glycerol glycol or glycerol glycol - ether, glycerol ester and p-toluenesulfonic acid ester.
  • phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate
  • phosphoric acid esters such as tributyl phosphate
  • adipic acid esters such as di- (2-ethylhexyl) adipate
  • stearates such as
  • Fixing agents are chemically based on polyvinyl alkyl ethers such as e.g. Polyvinyl methyl ether or ketones such as benzophenone, ethylene benzophenone.
  • Water is also particularly suitable as a solvent or diluent, optionally in a mixture with one or more of the above-mentioned organic chemical solvents or diluents, emulsifiers and dispersants.
  • a particularly effective wood protection is achieved through industrial impregnation processes, e.g. Vacuum, double vacuum or pressure process.
  • the ready-to-use compositions may also contain further insecticides and / or fungicides.
  • insecticides and fungicides mentioned in WO 94/29 268 are preferably suitable as additional admixing partners.
  • the compounds mentioned in this document are an integral part of the present application.
  • Insecticides such as chloropyriphos, phoxime, silafluofin, alphamethrin, cyfluthrin, cypermethrin, deltamethrin,
  • fungicides such as epoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, imazalil, dichlorofluoride, tolylfluoride, 3-iodo-2-propynylbutylcarbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro N-octylisothiazolin-3-one.
  • the preparation and use of the active compounds according to the invention can be seen from the examples below.
  • Dilute hydrochloric acid is added to the reaction mixture, the organic phase is separated off and the aqueous phase is extracted twice with dichloromethane.
  • the combined organic phases are washed twice with saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated in a water jet vacuum. The residue is stirred with ethanol, the solid is suction filtered, washed twice with a little ethanol, then twice with diethyl ether and dried.
  • Dilute hydrochloric acid is added to the reaction mixture, the organic phase is separated off and the aqueous phase is extracted once with dichloromethane.
  • the combined organic phases are washed once with water, dried over sodium sulfate, filtered and concentrated in a water jet vacuum. The residue is stirred with ethanol, the solid is filtered off with suction, washed with diethyl ether and dried.
  • 75 g (0.64 mol) of boron trichloride are introduced into 200 ml of 1,2-dichloroethane.
  • a solution of 70.8 g (0.5 mol) of 3-chloro-2-methylaniline in 120 ml of 1,2-dichloroethane is added dropwise at 0 ° C and the mixture is stirred at 20 ° C for 40 minutes.
  • a solution of 52.4 g (0.77 mol) of cyclopropanecarbonitrile in 55 ml of 1,2-dichloroethane is then added dropwise and the mixture is stirred at 20 ° C. for a further hour.
  • the reaction mixture is mixed with 5% sodium dihydrogen phosphate solution, the organic phase is separated off and the aqueous phase is extracted once with dichloromethane.
  • the combined organic phases are washed twice with saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated in a water jet vacuum. The residue is stirred with ethanol, the solid is suctioned off, first four times with a little ethanol, then three times with
  • 150 g (1.25 mol) of boron trichloride are introduced into 400 ml of 1,2-dichloroethane.
  • a solution of 141.5 g (1.0 mol) of 3-chloro-2-methylaniline in 150 ml of 1,2-dichloroethane is added dropwise at 0 ° C. and the mixture is stirred at 20 ° C. for 40 minutes.
  • a solution of 82.5 g (1.5 mol) of propionitrile is then added dropwise and the mixture is stirred at 20 ° C. for a further hour.
  • 227.6 g (1.2 mol) of titanium tetrachloride are added dropwise and the mixture is heated under reflux for 15 hours. After cooling, carefully drop it under ice cooling
  • Dilute hydrochloric acid is added to the reaction mixture, the organic phase is separated off and the aqueous phase is extracted once with dichloromethane.
  • the combined organic phases are washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated in a water jet vacuum.
  • the residue is stirred with ethanol and the solid formed is filtered off with suction.
  • the crude product is stirred again with a mixture of petroleum ether and diethyl ether, suction filtered again, washed three times with petroleum ether and dried on clay.
  • Dilute hydrochloric acid is added to the reaction mixture, the organic phase is separated off and the aqueous phase is extracted once with dichloromethane.
  • the combined organic phases are washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated in a water jet vacuum. The residue is stirred with ethanol, the solid is filtered off with suction, washed first twice with a little ethanol, then twice with diethyl ether and dried.
  • Emulsifier 3 parts by weight of alkylaryl polyglycol ether
  • Active ingredient with the specified amounts of solvent and emulsifier and dilute the concentrate with water to the desired concentration.
  • Plants are inoculated with an aqueous spore suspension of the pod mildew pathogen Podosphaera leucotricha. The plants are then placed in the greenhouse at about 23 ° C. and a relative humidity of about 70%.
  • Emulsifier 3 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Evaluation is carried out 10 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
  • the compounds of Preparation Examples 1, 2, 4, 5, 8, 13, 15 and 17 show an efficiency of up to 100% compared to the untreated control at an exemplary active ingredient application rate of 100 g / ha.
  • Emulsifier 3 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • the plants are then placed in the greenhouse at approx. 21 ° C. and a relative humidity of approx. 90%.
  • Evaluation is carried out 12 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with horseradish leaf beetle larvae (Phaedon cochleariae) while the leaves are still moist.
  • the kill is determined in%. 100% means that all beetle larvae have been killed; 0% means that no beetle larvae have been killed.
  • the compound of preparation example 16 shows a kill of 100% after 3 days at an exemplary active ingredient concentration of 0.1%.
  • a specified amount of active compound preparation of the desired concentrations is pipetted onto a standardized amount of artificial feeder. After the methanol has evaporated, about 20 eggs of the onion fly (Hylemyia antiqua) are placed on the feed.
  • the death of the eggs or larvae is determined in%. 100% means that all animals have been killed; 0% means that no animals have been killed.
  • compound (13) of the preparation examples shows a 100% degree of destruction at an active ingredient concentration of 0.05%.
  • the compounds 1, 13 and 15 are each incorporated in different concentrations in liquid agar culture media. After the nutrient medium has solidified, the test plates are inoculated with a cell suspension of Pseudomonas aeruginosa and with spores of Chaetonium globosum and penicillium brevicaule. The minimum inhibitory concentration is determined after an incubation period of 3 (bacteria) or 14 days (fungi). The compounds according to the invention show a pronounced antibacterial and anti-fertilizing activity (Table F).

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  • 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)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Nouveaux dérivés de phénylaminosulfonylurée, procédé de production desdits dérivés et leur utilisation comme fongicides.
PCT/EP1998/000803 1997-02-26 1998-02-13 Derives de phenylaminosulfonyluree en tant que fongicide et pesticide WO1998038172A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP53723998A JP2001513092A (ja) 1997-02-26 1998-02-13 殺菌・殺カビ剤並びに有害生物防除剤としてのフェニル−アミノ−スルホニル尿素誘導体
EP98910654A EP0973751A1 (fr) 1997-02-26 1998-02-13 Derives de phenylaminosulfonyluree en tant que fongicide et pesticide
AU64966/98A AU6496698A (en) 1997-02-26 1998-02-13 Phenyl-amino-sulfonyl-urea derivatives as fungicides and pesticides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1997107580 DE19707580A1 (de) 1997-02-26 1997-02-26 Phenylaminosulfonylharnstoffderivate
DE19707580.0 1997-02-26

Publications (1)

Publication Number Publication Date
WO1998038172A1 true WO1998038172A1 (fr) 1998-09-03

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JP (1) JP2001513092A (fr)
AU (1) AU6496698A (fr)
DE (1) DE19707580A1 (fr)
WO (1) WO1998038172A1 (fr)

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5815962A (ja) * 1981-07-21 1983-01-29 Mitsui Toatsu Chem Inc 新規スルホニルウレイド誘導体
DE3243533A1 (de) * 1981-12-03 1983-06-09 Sandoz-Patent-GmbH, 7850 Lörrach Sulfonamide als herbizide
DE3300569A1 (de) * 1982-01-12 1983-07-21 CIBA-GEIGY AG, 4002 Basel Triaza-verbindungen
US4592776A (en) * 1985-02-04 1986-06-03 Ppg Industries, Inc. Sulfamoyl urea derivatives
US4622065A (en) * 1984-11-01 1986-11-11 Ppg Industries, Inc. Sulfamoyl urea derivatives
DE4337847A1 (de) * 1993-11-05 1995-05-11 Bayer Ag Substituierte Phenylaminosulfonylharnstoffe
DE4435470A1 (de) * 1994-10-04 1996-04-11 Bayer Ag Substituierte Phenylaminosulfonylharnstoffe
US5559234A (en) * 1995-06-06 1996-09-24 American Cyanamid Company Process for the manufacture of herbicidal 1-{[2-(cyclopropylcarbonyl)phyenyl]sulfamoyl}-3-(4,6-dialkoxy-2-pyrimidinyl)urea compounds

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5815962A (ja) * 1981-07-21 1983-01-29 Mitsui Toatsu Chem Inc 新規スルホニルウレイド誘導体
DE3243533A1 (de) * 1981-12-03 1983-06-09 Sandoz-Patent-GmbH, 7850 Lörrach Sulfonamide als herbizide
DE3300569A1 (de) * 1982-01-12 1983-07-21 CIBA-GEIGY AG, 4002 Basel Triaza-verbindungen
US4622065A (en) * 1984-11-01 1986-11-11 Ppg Industries, Inc. Sulfamoyl urea derivatives
US4592776A (en) * 1985-02-04 1986-06-03 Ppg Industries, Inc. Sulfamoyl urea derivatives
DE4337847A1 (de) * 1993-11-05 1995-05-11 Bayer Ag Substituierte Phenylaminosulfonylharnstoffe
DE4435470A1 (de) * 1994-10-04 1996-04-11 Bayer Ag Substituierte Phenylaminosulfonylharnstoffe
US5559234A (en) * 1995-06-06 1996-09-24 American Cyanamid Company Process for the manufacture of herbicidal 1-{[2-(cyclopropylcarbonyl)phyenyl]sulfamoyl}-3-(4,6-dialkoxy-2-pyrimidinyl)urea compounds

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 007, no. 086 9 April 1983 (1983-04-09) *

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DE19707580A1 (de) 1998-08-27
EP0973751A1 (fr) 2000-01-26
AU6496698A (en) 1998-09-18

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