DE4234028A1 - New N-phenyl-carbamate, urea or amide derivs. - Google Patents

New N-phenyl-carbamate, urea or amide derivs.

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Publication number
DE4234028A1
DE4234028A1 DE4234028A DE4234028A DE4234028A1 DE 4234028 A1 DE4234028 A1 DE 4234028A1 DE 4234028 A DE4234028 A DE 4234028A DE 4234028 A DE4234028 A DE 4234028A DE 4234028 A1 DE4234028 A1 DE 4234028A1
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DE
Germany
Prior art keywords
chr
formula
alkyl
compound
alkenyl
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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Withdrawn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
DE4234028A
Other languages
German (de)
Inventor
Bernd Dr Mueller
Hubert Dr Sauter
Franz Dr Roehl
Gisela Dr Lorenz
Eberhard Dr Ammermann
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BASF SE
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BASF SE
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Application filed by BASF SE filed Critical BASF SE
Priority to DE4234028A priority Critical patent/DE4234028A1/en
Priority to EP93902227A priority patent/EP0624155B2/en
Priority to BR9305817A priority patent/BR9305817A/en
Priority to CZ19941785A priority patent/CZ288922B6/en
Priority to DE59308508T priority patent/DE59308508D1/en
Priority to NZ246603A priority patent/NZ246603A/en
Priority to DK93902227T priority patent/DK0624155T4/en
Priority to HU9401961A priority patent/HU217905B/en
Priority to US08/256,628 priority patent/US5824705A/en
Priority to SK907-94A priority patent/SK283351B6/en
Priority to RU94045970A priority patent/RU2129118C1/en
Priority to UA94085752A priority patent/UA37202C2/en
Priority to PCT/EP1993/000104 priority patent/WO1993015046A1/en
Priority to AT93902227T priority patent/ATE165818T1/en
Priority to ES93902227T priority patent/ES2116436T5/en
Priority to KR1019940702612A priority patent/KR100282840B1/en
Priority to AU33514/93A priority patent/AU671974B2/en
Priority to JP51289793A priority patent/JP3883566B2/en
Priority to CA002127110A priority patent/CA2127110C/en
Priority to IL10448993A priority patent/IL104489A/en
Priority to TW82100771A priority patent/TW247270B/zh
Publication of DE4234028A1 publication Critical patent/DE4234028A1/en
Priority to FI943523A priority patent/FI120766B/en
Priority to NO942814A priority patent/NO302467B1/en
Priority to AU52465/96A priority patent/AU680592B2/en
Priority to US09/110,884 priority patent/US5981532A/en
Priority to US09/275,767 priority patent/US6075148A/en
Priority to US09/527,118 priority patent/US6252083B1/en
Withdrawn legal-status Critical Current

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    • C07—ORGANIC CHEMISTRY
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    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • 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
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/20—N-Aryl derivatives thereof
    • 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
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
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    • C07C233/00—Carboxylic acid amides
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    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/24—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
    • C07C233/25—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
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    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
    • C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
    • C07C259/06—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
    • C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
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    • C07C271/62—Compounds containing any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylcarbamates
    • C07C271/66—Y being a hetero atom
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    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C275/32—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
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    • C07C313/08—Sulfenic acids; Derivatives thereof
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    • C07C313/30—Y being a hetero atom
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Abstract

N-(2-(A-B)-phenyl)-carbamate, urea, acetamide or propionamide derivs. of formula (I) and their acid- and base-addn. prods. are new. In (I), Z = OMe, NH2, NHMe, NMe2, Me, Et, CF3 or CCl3; X, Y = H, F, Cl, Br, CF3, CN, NO2, alkoxy, alkenyloxy, alkynyloxy, alkyl, alkenyl, or alkynyl; or X + Y = opt. substd. fused aromatic or heteroaromatic, alicyclic or heterocyclic, partially or completely hydrogenated ring; R1 = H, opt. substd. alkyl, alkenyl, alkynyl, cyclopropyl, cyclopropylmethyl, cyclobutyl, CH2CN, CH2OMe, COOMe or SR5, alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, cycloalkenyloxy or alkoxycarbonyloxy; A = O, S, -CR2=CR3, CHR20, CHR2S, -CHR2)N=C(R4)-, -CR2=N-O-, -O-N=C(R4)-, -C=C-, -CHR2CHR3-, -CHR2OCO-, -OCHR2- or a direct bond. B (opt. substd.) = alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, aryl, heteroaryl, heterocyclyl, H, opt. substd. aralkyl, opt. substd. heteroarylalkyl opt. substd. cycloalkylalkyl or opt. substd. cycloalkenylalkyl; R2, E3 = H, alkyl, alkenyl, alkynyl, or cycloalkyl; R4 = H, CN, alkyl, alkenyl, alkynyl, alkoxy or cycloalkyl; R5 = alkyl, cyclopropyl, cyclopropylmethyl or cyclobutyl.

Description

Die vorliegende Erfindung betrifft Verbindungen und ihre Verwen­ dung als Pflanzenschutzmittel, insbesondere zur Bekämpfung von Pilzen, Insekten, Nematoden und Spinnmilben.The present invention relates to compounds and their uses as a plant protection product, in particular for combating Fungi, insects, nematodes and spider mites.

Es ist bekannt Anilinderivate, z. B. den N-Phenyl-carbaminsäure­ i-propylester oder den entsprechenden N-3-Chlorphenylester (GB 574995) oder den N-3,4-Dichlorphenyl-carbaminsäuremethylester (BE 612 550) als Pflanzenschutzmittel zu verwenden. Ihre fungi­ zide Wirkung ist jedoch unbefriedigend.Aniline derivatives, e.g. B. the N-phenyl-carbamic acid i-propyl ester or the corresponding N-3-chlorophenyl ester (GB 574995) or the N-3,4-dichlorophenyl-carbamic acid methyl ester (BE 612 550) to be used as a plant protection product. Your fungi However, the zide effect is unsatisfactory.

Es wurde nun überraschend gefunden, daß Verbindungen der Formel IIt has now surprisingly been found that compounds of the formula I

in der die Substituenten die folgenden Bedeutungen haben:
X und Y bedeuten unabhängig voneinander F, Cl, Br, CF3, CN, NO2, Alkoxy, Alkenyloxy, Alkinyloxy, Alkyl, Alkenyl oder Alkinyl oder können zu einem ggf. substituierten aromatischen oder hetero­ aromatischen, alicyclischen oder heterocyclischen, partiell oder vollständig hydrierten Ring kondensiert sein, oder Y bedeutet Wasserstoff.in which the substituents have the following meanings:
X and Y independently of one another represent F, Cl, Br, CF 3 , CN, NO 2 , alkoxy, alkenyloxy, alkynyloxy, alkyl, alkenyl or alkynyl or can be partially or completely to an optionally substituted aromatic or heteroaromatic, alicyclic or heterocyclic hydrogenated ring must be condensed, or Y means hydrogen.

R1 kann ggf. substituiert sein und bedeutet Alkyl, Alkenyl, Alkinyl, Cycloalkyl, Cycloalkenyl oder -CO2-Alkyl, bevorzugt C1-C4-Alkyl und besonders bevorzugt Methyl oder Ethyl.R 1 can optionally be substituted and means alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl or -CO 2 alkyl, preferably C 1 -C 4 alkyl and particularly preferably methyl or ethyl.

X und Y bedeuten unabhängig voneinander bevorzugt C1-C4-Alkyl, be­ sonders bevorzugt Methyl, bevorzugt C1-C4-Alkoxy, besonders bevor­ zugt Methyl, bevorzugt C1-C4-Alkoxy, besonders bevorzugt Methoxy, sowie besonders bevorzugt Fluor oder Chlor. X and Y independently of one another are preferably C 1 -C 4 -alkyl, particularly preferably methyl, preferably C 1 -C 4 -alkoxy, particularly preferably methyl, preferably C 1 -C 4 -alkoxy, particularly preferably methoxy, and particularly preferably Fluorine or chlorine.

A bedeutet -O-, -S-, -CR2=CR3-, CHR2-O-, -CHR2-S-, -CHR2-Q-N=C(R4)-, -CR2=N-O-, -O-N=C (R4)-, -C≡C-, -CHR2-CHR3-, -CHR2-O-CO-, -O-CHR2- oder eine Einfachbindung. A bedeutet bevor­ zugt -O-, -CH2O-, -CH2-O-N=C(CH3)- oder -CH=CH- oder -CH2-S-.A means -O-, -S-, -CR 2 = CR 3 -, CHR 2 -O-, -CHR 2 -S-, -CHR 2 -QN = C (R 4 ) -, -CR 2 = NO- , -ON = C (R 4 ) -, -C≡C-, -CHR 2 -CHR 3 -, -CHR 2 -O-CO-, -O-CHR 2 - or a single bond. A preferably means -O-, -CH 2 O-, -CH 2 -ON = C (CH 3 ) - or -CH = CH- or -CH 2 -S-.

B kann ggf. substituiert sein und bedeutet Alkyl, Alkenyl, Alkinyl, Cycloalkyl, Cycloalkenyl, Cycloalkinyl, Aryl, Hetaryl, Heterocyclyl oder Wasserstoff. B bedeutet bevorzugt Aryl oder Hetaryl.B can optionally be substituted and means alkyl, alkenyl, Alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, aryl, hetaryl, Heterocyclyl or hydrogen. B is preferably aryl or Hetaryl.

-A-B bedeutet besonders bevorzugt -CH2-O-Phenyl, -CH2-S-Hetaryl, -O-Phenyl, -O-Hetaryl oder -CH2-O-N=C (CH2) -Phenyl, wobei die Phe­ nyl- bzw. Hetarylreste substituiert sein können. Bevorzugte Sub­ stituenten für B sind Wasserstoff, Halogen (F, Cl, Br), CN, C1-C4-Alkyl, C1-C4-Alkoxy, ggf. subst. Phenoxy, ggf. subst. Het­ aryl, -C(C1-C4-Alkyl)=N-O-(C1-C4-Alkyl) oder -C(C1-C4-Al­ kyl)=N-O-(C1-C4-Alkenyl).-AB particularly preferably denotes -CH 2 -O-phenyl, -CH 2 -S-hetaryl, -O-phenyl, -O-hetaryl or -CH 2 -ON = C (CH 2 ) -phenyl, the phenyl- or hetaryl radicals can be substituted. Preferred sub-substituents for B are hydrogen, halogen (F, Cl, Br), CN, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, optionally subst. Phenoxy, optionally subst. Het aryl, -C (C 1 -C 4 alkyl) = NO- (C 1 -C 4 alkyl) or -C (C 1 -C 4 alkyl) = NO- (C 1 -C 4 alkenyl ).

R2 und R3 bedeuten unabhängig voneinander Wasserstoff, Alkyl, Alkenyl, Alkinyl oder Cycloalkyl, besonders bevorzugt Wasserstoff und R4 bedeutet Wasserstoff, Cyano, Alkyl, Alkenyl, Alkinyl, Cycloalkyl oder Alkoxy, bevorzugt Alkyl und besonders bevorzugt Methyl,
sowie deren pflanzenverträgliche Säureadditionsprodukte oder Ba­ senadditionsprodukte neben einer hohen fungitoxischen, insektizi­ den, nematiziden und akariziden Wirkung auch eine sehr gute Pflanzenverträglichkeit besitzen.R 2 and R 3 independently of one another are hydrogen, alkyl, alkenyl, alkynyl or cycloalkyl, particularly preferably hydrogen and R 4 is hydrogen, cyano, alkyl, alkenyl, alkynyl, cycloalkyl or alkoxy, preferably alkyl and particularly preferably methyl,
and their plant-compatible acid addition products or base addition products, in addition to a high fungitoxic, insecticidal, nematicidal and acaricidal action, also have very good plant tolerance.

Säuren für Säureadditionsprodukte sind z. B. Mineralsäure, wie beispielsweise Chlorwasserstoffsäure, Bromwasserstoffsäure, Phosp­ horsäure, Schwefelsäure, Salpetersäure, oder Carbonsäuren, wie Ameisensäure, Essigsäure, Oxalsäure, Malonsäure, Milchsäure, Äp­ felsäure, Bernsteinsäure, Weinsäure, Zitronensäure, Salicylsäure; p-Toluolsulfonsäure, Dodecylbenzolsulfonsäure, oder aber auch allgemein Protonen-acide Verbindungen, z. B. Saccharin.Acids for acid addition products are e.g. B. mineral acid, such as for example hydrochloric acid, hydrobromic acid, phosp horse acid, sulfuric acid, nitric acid, or carboxylic acids, such as Formic acid, acetic acid, oxalic acid, malonic acid, lactic acid, Äp rock acid, succinic acid, tartaric acid, citric acid, salicylic acid; p-toluenesulfonic acid, dodecylbenzenesulfonic acid, or else generally proton acidic compounds, e.g. B. saccharin.

Basen für Basenadditionsprodukte sind z. B. Kalium-, Natrium-, -hydroxid, -carbonat, Ammoniumhydroxid.Bases for base addition products are e.g. B. potassium, sodium, -hydroxide, -carbonate, ammonium hydroxide.

Die neuen Verbindungen der Formel I können bei der Herstellung als Gemische von Stereoisomeren (E/Z-Isomere, Diastereomere, Enantiomere) anfallen, die in üblicher Weise, z. B. durch Kristal­ lisation oder Chromatographie, in die Einzelkomponenten getrennt werden können. Sowohl die einzelnen Isomeren als auch ihre Gemi­ sche können als Fungizide, Akarizide, Nematizide oder Insektizide verwendet werden und werden von der Erfindung erfaßt.The new compounds of formula I can in the preparation as mixtures of stereoisomers (E / Z isomers, diastereomers, Enantiomers) are obtained, which in the usual way, for. B. by Kristal lisation or chromatography, separated into the individual components can be. Both the individual isomers and their mixtures  can be used as fungicides, acaricides, nematicides or insecticides are used and are covered by the invention.

R1 kann beliebig substituiert sein, beispielsweise mit 1-4 glei­ chen oder verschiedenen Substituenten R7, so daß R1 auch Gruppen umfaßt wie beispielsweise -CH2-CN oder -CH2-O-CH3, oder kann funk­ tionelle Gruppen tragen, so daß R1 auch Gruppen umfaßt wie -CO- O-CH3.R 1 can be substituted as desired, for example with 1-4 identical or different substituents R 7 , so that R 1 also includes groups such as -CH 2 -CN or -CH 2 -O-CH 3 , or can carry functional groups , so that R 1 also includes groups such as -CO- O-CH 3 .

B kann beliebig substituiert sein, beispielsweise mit 1-4 glei­ chen oder verschiedenen Substituenten R7, kann funktionelle Grup­ pen enthalten wie z. B. =O, -COO-Alkyl, -OH oder -CO-N(Alkyl)2, so daß B auch Gruppen umfaßt wie z. B.B can be substituted as desired, for example with 1-4 identical or different substituents R 7 , can contain functional groups such as, for. B. = O, -COO-alkyl, -OH or -CO-N (alkyl) 2 , so that B also includes groups such as. B.

-CH2-CH(COO-Alkyl)-CH3 oder -CH2-CH(COON(Alkyl)2)-CH3, oder kann in einer Kohlenstoffkette auch Heteroatome wie N, O oder S enthal­ ten, so daß B auch Gruppen umfaßt wie z. B. -CH2-O-CH3, -CH2-S-CH3, -CH2-S(=O)-CH3 oder -CH2-NH-CH3.-CH 2 -CH (COO-alkyl) -CH 3 or -CH 2 -CH (COON (alkyl) 2 ) -CH 3 , or can also contain heteroatoms such as N, O or S in a carbon chain, so that B also Groups include such. B. -CH 2 -O-CH 3 , -CH 2 -S-CH 3 , -CH 2 -S (= O) -CH 3 or -CH 2 -NH-CH 3 .

Zwei benachbarte Substituenten R7 können zusammen mit den Kohlen­ stoffatomen, deren Substituenten sie sind, einen carbocyclischen hydrierten, partiell ungesättigten oder aromatischen Ring mit 3-14 Kohlenstoffatomen oder auch einen heterocyclischen hydrier­ ten, partiell ungesättigten oder heteroaromatischen Ring mit 3-14 Ringatomen, davon 1-4 Heteroatome aus der Gruppe N, O, S bilden.Two adjacent substituents R 7 together with the carbon atoms, the substituents of which they are, can be a carbocyclic hydrogenated, partially unsaturated or aromatic ring with 3-14 carbon atoms or a heterocyclic hydrogenated, partially unsaturated or heteroaromatic ring with 3-14 ring atoms, thereof Form 1-4 heteroatoms from the group N, O, S.

R7 kann beliebig substituiert sein, beispielsweise mit 1-4 glei­ chen oder verschiedenen Substituenten R8 und R7 bedeutet bei­ spielsweise Wasserstoff, Halogen, Cyano, Nitro, Haloalkyl, Alkyl, Haloalkoxy, Alkenyl, Alkinyl, Cycloalkyl, Aryl, Hetaryl, Hetero­ cyclyl, Cycloalkenyl, Alkoxy, Alkenyloxy, Alkinyloxy, Cycloalky­ loxy, Aryloxy, Hetaryloxy, Heterocyclyloxy, Cycloalkenyloxy, Al­ koximino, Alkenyloxyimino, Alkinyloximino, Cycloalkyloximino, Cy­ cloalkenyloximino, Aryloximino, Hetaryloximino, Heterocyclyloxi­ mino, Alkoxycarbonyl, Alkenyloxycarbonyl, Alkinyloxycarbonyl, Cy­ cloalkyloxycarbonyl, Aryloxycarbonyl, Hetaryloxycarbonyl, Hetero­ cyclyloxycarbonyl, Cycloalkenyloxycarbonyl, Alkylaminocarbonyl, Dialkylaminocarbonyl, Alkenylaminocarbonyl, Dialkenylaminocarbo­ nyl, Alkylthio, Alkenylthio, Alkinylthio, Cycloalkylthio, Arylt­ hio, Hetarylthio, Heterocyclylthio, Cycloalkenylthio, Alkylamino, Alkenylamino, Alkinylamino, Cycloalkylamino, Arylamino, Hetaryla­ mino, Heterocyclylamino, Cycloalkenylamino, Alkylcarbonyl, Alkenylcarbonyl, Alkinylcarbonyl, Cycloalkylcarbonyl, Arylcarbo­ nyl, Hetarylcarbonyl, Heterocyclylcarbonyl, Cycloalkenylcarbonyl, Alkylsulfoxyl, Alkenylsulfoxyl, Alkinylsulfoxyl, Cycloalkylsulfo­ xyl, Arylsulfoxyl, Hetarylsulfoxyl, Heterocyclylsulfoxyl, Cyclo­ alkenylsulfoxyl, Alkylsulfonyl, Alkenylsulfonyl, Alkinylsulfonyl, Cycloalkylsulfonyl, Arylsulfonyl, Hetarylsulfonyl, Heterocyclyl­ sulfonyl, Cycloalkenylsulfonyl, Alkylsulfinyl, Alkenylsulfinyl, Alkinylsulfinyl, Cycloalkylsulfinyl, Arylsulfinyl, Hetarylsulfi­ nyl, Heterocyclylsulfinyl oder Cycloalkenylsulfinyl.R 7 can be substituted as desired, for example with 1-4 identical or different substituents R 8 and R 7 means, for example, hydrogen, halogen, cyano, nitro, haloalkyl, alkyl, haloalkoxy, alkenyl, alkynyl, cycloalkyl, aryl, hetaryl, hetero cyclyl, cycloalkenyl, alkoxy, alkenyloxy, alkynyloxy, cycloalky loxy, aryloxy, hetaryloxy, heterocyclyloxy, cycloalkenyloxy, alkoximino, alkenyloxyimino, alkynyloximino, cycloalkyloximino, cy cloalkenyloximoxy, oxyoxyoxycarbonyl, aryloxyloxyoxyoxy , Hetaryloxycarbonyl, hetero cyclyloxycarbonyl, cycloalkenyloxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkenylaminocarbonyl, Dialkenylaminocarbo nyl, alkylthio, alkenylthio, alkynylthio, cycloalkylthio, Arylt hio, hetarylthio, heterocyclylthio, Cycloalkenylthio, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, arylamino, Hetaryla mino, heterocyclylamino, cycloalkylene kenylamino, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, Arylcarbo nyl, hetarylcarbonyl, heterocyclylcarbonyl, cycloalkenylcarbonyl, alkylsulfoxyl, Alkenylsulfoxyl, Alkinylsulfoxyl, Cycloalkylsulfo xyl, arylsulfoxyl, Hetarylsulfoxyl, Heterocyclylsulfoxyl, cyclo alkenylsulfoxyl, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, hetarylsulfonyl, heterocyclyl sulfonyl, cycloalkenylsulfonyl, alkylsulfinyl, alkenylsulfinyl, alkynylsulfinyl, cycloalkylsulfinyl, arylsulfinyl, hetarylsulfonyl, heterocyclylsulfinyl or cycloalkenylsulfinyl.

R8 ist ein beliebiger Substituent und bedeutet beispielsweise Was­ serstoff, Halogen, Cyano, Nitro, Haloalkyl, Alkyl, Haloalkoxy, Alkenyl, Alkinyl, Cycloalkyl, Aryl, Hetaryl, Heterocyclyl, Cyclo­ alkenyl, Alkoxy, Alkenyloxy, Alkinyloxy, Cycloalkyloxy, Aryloxy, Hetaryloxy, Heterocyclyloxy, Cycloalkenyloxy, Alkoximino, Alkeny­ loximino, Alkinyloximino, Cycloalkyloximino, Cycloalkenyloximino, Aryloximino, Hetaryloximino, Heterocyclyloximino, Alkoxycarbonyl, Alkenyloxycarbonyl, Alkinyloxycarbonyl, Cycloalkyloxycarbonyl, Aryloxycarbonyl, Hetaryloxycarbonyl, Heterocyclyloxycarbonyl, Cy­ cloalkenyloxycarbonyl, Alkylaminocarbonyl, Dialkylaminocarbonyl, Alkenylaminocarbonyl, Dialkenylaminocarbonyl, Alkylthio, Alkenyl­ thio, Alkinylthio, Cycloalkylthio, Arylthio, Hetarylthio, Hetero­ cyclylthio, Cycloalkenylthio, Alkylamino, Alkenylamino, Alkinyla­ mino, Cycloalkylamino, Arylamino, Hetarylamino, Heterocyclyla­ mino, Cycloalkenylamino, Alkylcarbonyl, Alkenylcarbonyl, Alkinyl­ carbonyl, Cycloalkylcarbonyl, Arylcarbonyl, Hetarylcarbonyl, He­ terocyclylcarbonyl, Cycloalkenylcarbonyl, Alkylsulfoxyl, Alkenyl­ sulfoxyl, Alkinylsulfoxyl, Cycloalkylsulfoxyl, Arylsulfoxyl, He­ tarylsulfoxyl, Heterocyclylsulfoxyl, Cycloalkenylsulfoxyl, Alkyl­ sulfonyl, Alkenylsulfonyl, Alkinylsulfonyl, Cycloalkylsulfonyl, Arylsulfonyl, Hetarylsulfonyl, Heterocyclylsulfonyl, Cycloalke­ nylsulfonyl, Alkylsulfinyl, Alkenylsulfinyl, Alkinylsulfinyl, Cy­ cloalkylsulfinyl, Arylsulfinyl, Hetarylsulfinyl, Heterocyclylsul­ finyl oder Cycloalkenylsulfinyl.R 8 is any substituent and means, for example, what is hydrogen, halogen, cyano, nitro, haloalkyl, alkyl, haloalkoxy, alkenyl, alkynyl, cycloalkyl, aryl, hetaryl, heterocyclyl, cyclo alkenyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, aryloxy, hetaryloxy , heterocyclyloxy, cycloalkenyloxy, alkoximino, Alkeny loximino, Alkinyloximino, Cycloalkyloximino, Cycloalkenyloximino, Aryloximino, Hetaryloximino, Heterocyclyloximino, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, cycloalkyloxycarbonyl, aryloxycarbonyl, Hetaryloxycarbonyl, heterocyclyloxycarbonyl, Cy cloalkenyloxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkenylaminocarbonyl, dialkenylaminocarbonyl, alkylthio, alkenyl thio, alkynylthio, cycloalkylthio, arylthio, hetarylthio, hetero cyclylthio, cycloalkenylthio, alkylamino, alkenylamino, alkinyla mino, cycloalkylamino, arylamino, hetarylamino, heterocyclyla mino, cycloalkenylamino, carbonyl, carbonyl, carbonyl, carbonyl, carbonyl, carbonyl , Arylcarbonyl, hetarylcarbonyl, He terocyclylcarbonyl, cycloalkenylcarbonyl, alkylsulfoxyl, alkenyl sulfoxyl, Alkinylsulfoxyl, Cycloalkylsulfoxyl, arylsulfoxyl, He tarylsulfoxyl, Heterocyclylsulfoxyl, Cycloalkenylsulfoxyl, alkyl sulfonyl, alkenylsulfonyl, alkynylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, hetarylsulfonyl, heterocyclylsulfonyl, cycloalkenyl nylsulfonyl, alkylsulfinyl, alkenylsulfinyl, Alkynylsulfinyl, cycloalkylsulfinyl, arylsulfinyl, hetarylsulfinyl, heterocyclylsulfinyl or cycloalkenylsulfinyl.

Die oben genannten Alkyle können beliebig substituiert sein, bei spielsweise mit 1-4 gleichen oder verschiedenen Substituenten R7, die Alkyle besitzen bevorzugt 1-6 Kohlenstoffatome und be­ deuten beispielsweise Methyl, Ethyl, Propyl, n-Propyl, i-Propyl, Butyl, n-Butyl, i-Butyl, t-Butyl, s-Butyl, Pentyl oder Hexyl.The abovementioned alkyls can be substituted as desired, for example with 1-4 identical or different substituents R 7 , the alkyls preferably have 1-6 carbon atoms and are, for example, methyl, ethyl, propyl, n-propyl, i-propyl, butyl, n-butyl, i-butyl, t-butyl, s-butyl, pentyl or hexyl.

Die oben genannten Alkenyle können beliebig substituiert sein, beispielsweise mit 1-4 gleichen oder verschiedenen Substituen­ ten R7, die Alkenyle besitzen bevorzugt 2 - 6 Kohlenstoffatome und bedeuten beispielsweise Ethenyl, Propenyl, Propen-(1)-yl, Propen-(2)-yl, Propen-(1)-yl-(2), Butenyl, Buten-(1)-yl, Bu­ ten-(2)-yl, Buten-(3)-yl, Buten-(1)-yl-(3), Buten-(2)-yl-(2), Bu­ ten-(1)-yl-(2), 2-Methyl-propenyl-(1), 2-Methyl-propenyl-(2), Pentenyl oder Hexenyl.The above-mentioned alkenyls can be substituted as desired, for example with 1-4 identical or different substituents R 7 , the alkenyls preferably have 2-6 carbon atoms and are, for example, ethenyl, propenyl, propen- (1) -yl, propen- (2) -yl, propene- (1) -yl- (2), butenyl, butene- (1) -yl, butene- (2) -yl, butene- (3) -yl, butene- (1) -yl- (3), butene- (2) -yl- (2), butene- (1) -yl- (2), 2-methyl-propenyl- (1), 2-methyl-propenyl- (2), pentenyl or hexenyl.

Die oben genannten Alkinyle können beliebig substituiert sein, beispielsweise mit 1-4 gleichen oder verschiedenen Substituen­ ten R7, die Alkinyle besitzen bevorzugt 2-6 Kohlenstoffatome und bedeuten beispielsweise Ethinyl, Propinyl, Propin-(1)-yl, Pro­ pin-(3)-yl, Butin, Butin-(1)-yl, Butin-(2)-yl, Butin-(3)-yl, 1-Methyl-propin-(2)-yl, Pentinyl oder Hexinyl.The above-mentioned alkynyls can be substituted as desired, for example with 1-4 identical or different substituents R 7 , the alkynyls preferably have 2-6 carbon atoms and mean, for example, ethynyl, propynyl, propin (1) yl, propin (3 ) -yl, butyne, butyne (1) -yl, butine (2) -yl, butine (3) -yl, 1-methyl-propine (2) -yl, pentynyl or hexynyl.

Die vorstehend genannten Halogene bedeuten Fluor, Chlor, Brom oder Iod.The above halogens mean fluorine, chlorine, bromine or iodine.

Die oben genannten Cycloalkylreste können beliebig substituiert sein, beispielsweise mit 1-4 gleichen oder verschiedenen Sub­ stituenten R7, die Cycloalkyle besitzen bevorzugt 3-10 Kohlen­ stoffatome und bedeuten beispielsweise Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Cycloheptyl, Cyclooctyl, Cyclononyl, Cy­ clodecyl, Bornanyl, Norbornanyl, Dicyclohexyl, Bicyclo[3,3,0]octyl, Bicyclo[3,2,1]octyl, Bicyclo[2,2,2]octyl oder Bicyclo[3,3,1]nonyl.The above-mentioned cycloalkyl radicals can be substituted as desired, for example with 1-4 identical or different substituents R 7 , the cycloalkyls preferably have 3-10 carbon atoms and mean, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl , Bornanyl, Norbornanyl, Dicyclohexyl, Bicyclo [3,3,0] octyl, Bicyclo [3,2,1] octyl, Bicyclo [2,2,2] octyl or Bicyclo [3,3,1] nonyl.

Die oben genannten Cycloalkenylreste können beliebig substituiert sein, beispielsweise mit 1-4 gleichen oder verschiedenen Sub­ stituenten R7, die Cycloalkenyle besitzen bevorzugt 3-10 Kohlen­ stoffatome und bedeuten beispielsweise Cyclopropenyl, Cyclobute­ nyl, Cyclopentenyl, Cyclohexenyl, Cycloheptenyl, Cyclooctenyl, Cyclononenyl, Cyclodecenyl, Bornenyl, Norbornenyl, Bicyclo[3,3,0]octenyl, Bicyclo[3,2,1]octeny1, Bicyclo[2,2,2]octe­ nyl oder Bicyclo[3,3,1]nonenyl.The above-mentioned cycloalkenyl radicals can be substituted as desired, for example with 1-4 identical or different substituents R 7 , the cycloalkenyls preferably have 3-10 carbon atoms and mean, for example, cyclopropenyl, cyclobutylene, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, cyclononenyl, cyclodecenyl , Bornenyl, Norbornenyl, Bicyclo [3,3,0] octenyl, Bicyclo [3,2,1] octeny1, Bicyclo [2,2,2] octe nyl or Bicyclo [3,3,1] nonenyl.

Die oben genannten Cycloalkinylreste können beliebig substituiert sein, beispielsweise mit 1-4 gleichen oder verschiedenen Sub­ stituenten R7, die Cycloalkinyle besitzen bevorzugt 6-12 Kohlen­ stoffatome und bedeuten beispielsweise Cyclohexin, Cycloheptin, Cyclooctin, Cyclononin, Cyclodecin, Cycloundecin oder Cyclodode­ cin.The above-mentioned cycloalkynyl radicals can be substituted as desired, for example with 1-4 identical or different substituents R 7 , the cycloalkynyls preferably have 6-12 carbon atoms and mean, for example, cyclohexine, cycloheptin, cyclooctin, cyclononine, cyclodecin, cycloundecin or cyclodode cin.

Die vorstehend genannten Haloalkylreste bedeuten bevorzugt C1-C4-Halogenalkyl, besonders C1-C2-Halogenalkyl wie Chlormethyl, Dichlormethyl, Trichlormethyl, Fluromethyl, Difluormethyl, Tri­ fluormethyl, Chlorfluormethyl, Dichlorfluormethyl, Chloridfluor­ methyl, 1-Fluorethyl, 2-Fluorethyl, 2,2-Difluorethyl, 2,2,2-Tri­ fluorethy1, 2-Chlor-2-fluorethyl, 2-Chlor-2,2-difluorethyl, 2,2-Dichlor-2-fluorethyl, 2,2,2-Trichlorethyl oder Pentafluor­ ethyl. The above-mentioned haloalkyl radicals are preferably C 1 -C 4 haloalkyl, especially C 1 -C 2 haloalkyl such as chloromethyl, dichloromethyl, trichloromethyl, fluromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chloride fluoromethyl, 1-fluoroethyl, 2-fluoroethyl , 2,2-difluoroethyl, 2,2,2-tri fluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2- Trichloroethyl or pentafluoroethyl.

Die vorstehend genannten Haloalkoxyreste bedeuten bevorzugt C1-C4-Halogenalkoxy, besonders C1-C2-Halogenalkyloxy wie Chlorme­ thyloxy, Dichlormethyloxy, Trichlormethyloxy, Fluormethyloxy, Di­ fluormethyloxy, Trifluormethyloxy, Chlorfluormethyloxy, Dichlor­ fluormethyloxy, Chlordifluormethyloxy, 1-Fluorethyloxy, 2-Fluore­ thyloxy, 2,2-Difluorethyloxy, 2,2,2-Trifluorethyloxy, 2-Chlor-2-fluorethyloxy, 2-Chlor-2-2-difluorethyloxy, 2,2-Dichlor-2-fluorethyloxy, 2,2,2-Tri-chlorethyloxy oder Penta­ fluorethyloxy.The above-mentioned haloalkoxy radicals are preferably C 1 -C 4 haloalkoxy, especially C 1 -C 2 haloalkyloxy such as chloromethyloxy, dichloromethyloxy, trichloromethyloxy, fluoromethyloxy, difluoromethyloxy, trifluoromethyloxy, chlorofluoromethyloxy, dichlorofluoromethyloxy, chlorodifluoromethyloxy, 2-fluoroethyloxy, 1-fluoroethyloxy Fluoroethyloxy, 2,2-difluoroethyloxy, 2,2,2-trifluoroethyloxy, 2-chloro-2-fluoroethyloxy, 2-chloro-2-2-difluoroethyloxy, 2,2-dichloro-2-fluoroethyloxy, 2,2,2 -Tri-chloroethyloxy or penta fluoroethyloxy.

Die vorstehend genannten Aryle können beliebig substituiert sein, beispielsweise mit 1-4 gleichen oder verschiedenen Substituen­ ten R7, und die Aryle bedeuten bevorzugt Phenyl, 1-Naphthyl, 2-Naphthyl, 1-Anthracenyl, 2-Anthracenyl oder 9-Anthracenyl.The above aryls can be substituted as desired, for example with 1-4 identical or different substituents R 7 , and the aryls are preferably phenyl, 1-naphthyl, 2-naphthyl, 1-anthracenyl, 2-anthracenyl or 9-anthracenyl.

Die vorstehend genannten Hetaryle können beliebig substituiert sein, beispielsweise mit 1-4 gleichen oder verschiedenen Sub­ stituenten R7, und die Hetaryle bedeuten bevorzugt Furyl, 2-Furyl, 3-Furyl, Thienyl, 2-Thienyl, 3-Thienyl, Pyrrolyl, 1-Pyrrolyl, 2-Pyrrolyl, 3-Pyrrolyl, Isoxazolyl, 3-Isoxazolyl, 4-Isoxazolyl, 5-Isoxazolyl, Isothiozolyl, 3-Isothiozolyl, 4-Isothiozolyl, 5-Isothiozolyl, Pyrazolyl, 1-Pyrazolyl, 3-Pyrazolyl, 4-Pyrazolyl, 5-Pyrazolyl, Oxazolyl, 2-Oxazolyl, 4-Oxazolyl, 5-Oxazolyl, Thiazolyl, 2-Thiazolyl, 4-Thiazolyl, 5-Thiazolyl, Imidazolyl, 1-Imidazolyl, 2-Imidazolyl, 4-Imidazolyl, 5-Imidazolyl, 1,2,3-Thiadiazolyl, 1,2,4-Thiadiazolyl, 1,2,5-Thiadiazolyl, 1,3,4-Thiadiazolyl, Tetrazolyl, 1,2,3,4-Thiatriazolyl, 1,2,3,4-Oxatriazolyl, Pyridyl, 2-Pyridyl, 3-Pyridyl, 4-Pyridyl, Pyridazinyl, 3-Pyridazinyl, 4-Pyridazinyl, Pyrimidinyl, 2-Pyrimidinyl, 4-Pyrimidinyl, 5-Pyrimidinyl, Pyrazinyl, 2-Pyrazinyl, 3-Pyrazinyl, 1,2,4-Triazinyl, 1,3,5-Triazinyl oder 1,2,4,5-Tetrazinyl.The above-mentioned hetaryls can be substituted as desired, for example with 1-4 identical or different substituents R 7 , and the hetaryls are preferably furyl, 2-furyl, 3-furyl, thienyl, 2-thienyl, 3-thienyl, pyrrolyl, 1 -Pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, isoxazolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, isothiozolyl, 3-isothiozolyl, 4-isothiozolyl, 5-isothiozolyl, pyrazolyl, 1-pyrazolyl, 3- -Pyrazolyl, 5-pyrazolyl, oxazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, thiazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, imidazolyl, 1-imidazolyl, 2-imidazolyl, 4-imidazolyl, 5 -Imidazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, tetrazolyl, 1,2,3,4-thiatriazolyl, 1,2 , 3,4-oxatriazolyl, pyridyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, pyridazinyl, 3-pyridazinyl, 4-pyridazinyl, pyrimidinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, pyrazinyl, 2-pyrazinyl , 3-pyrazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl or 1,2,4,5-tetrazinyl.

Dabei können benachbarte Substituenten des Heteroaromaten konden­ siert sein zu einem aromatischen oder heteroaromatischen Ring, so daß Hetaryl auch kondensierte Ringsysteme umfaßt wie z. B. Benzo­ furanyl, Isobenzofuranyl, 1-Benzothienyl, 2-Benzothienyl, Indo­ lyl, Isoindolyl, Benzisoxazolyl, Benzoxazolyl, Benzisothiazolyl, Benzthiazolyl, 2-Benzthiazolyl, 4-Benzthiazolyl, 5-Benzthiazolyl, 6-Benzthiazolyl, 7-Benzthiazolyl, Indazolyl, Benzimidazolyl, Benzthiazolyl, Benzofurazanyl, Dibenzofuranyl, Dibenzothienyl, Acridinyl, Phenanthridinyl, Carbazolyl, Chinolinyl, Isochinoli­ nyl, Phthalazinyl, Chinazolinyl, Chinoxalinyl, Cinnolinyl, 1,5-Naphthyridinyl, 1,6-Naphthyridinyl, 1,7-Naphthyridinyl, 1,8-Naphthyridinyl, Pteridinyl, Pyrrolopyridinyl, Pyrrolopyrida­ zinyl, Pyrrolopyrimidinyl, Pyrrolopyrazinyl, Pyrrolotriazinyl, Furopyridinyl, Furopyridazinyl, Furopyrimidinyl, Furopyrazinyl, Furotriazinyl, Thienopyridinyl, Thienopyridazinyl, Thienopyrimi­ dinyl, Thienopyrazinyl, Thienotriazinyl, Imidazopyridazinyl, Imi­ dazopyrimidinyl, Imidazopyrazinyl, Pyrazolopyridinyl, Pyrazolopy­ ridazinyl, Pyrazolopyrimidinyl, Pyrazolopyrazinyl, Isoxazolopyra­ zinyl, Oxazolopyridinyl, Oxazolopyridazinyl, Oxazolopyrimidinyl, Oxazolopyrazinyl, Thiazolopyridinyl, Thiazolopyridazinyl, Iso­ thiazolopyrazinyl, Triazolopyridinyl, Triazolopyridazinyl, Tria­ zolopyrimidinyl oder Triazolopyrazinyl.Adjacent substituents of the heteroaromatic can condense be an aromatic or heteroaromatic ring, so that hetaryl also includes condensed ring systems such. B. Benzo furanyl, isobenzofuranyl, 1-benzothienyl, 2-benzothienyl, indo lyl, isoindolyl, benzisoxazolyl, benzoxazolyl, benzisothiazolyl, Benzothiazolyl, 2-benzthiazolyl, 4-benzthiazolyl, 5-benzthiazolyl, 6-benzothiazolyl, 7-benzthiazolyl, indazolyl, benzimidazolyl, Benzthiazolyl, benzofurazanyl, dibenzofuranyl, dibenzothienyl, Acridinyl, phenanthridinyl, carbazolyl, quinolinyl, isoquinoli nyl, phthalazinyl, quinazolinyl, quinoxalinyl, cinnolinyl, 1,5-naphthyridinyl, 1,6-naphthyridinyl, 1,7-naphthyridinyl, 1,8-naphthyridinyl, pteridinyl, pyrrolopyridinyl, pyrrolopyrida zinyl, pyrrolopyrimidinyl, pyrrolopyrazinyl, pyrrolotriazinyl, Furopyridinyl, furopyridazinyl, furopyrimidinyl, furopyrazinyl,  Furotriazinyl, thienopyridinyl, thienopyridazinyl, thienopyrimi dinyl, thienopyrazinyl, thienotriazinyl, imidazopyridazinyl, imi dazopyrimidinyl, imidazopyrazinyl, pyrazolopyridinyl, pyrazolopy ridazinyl, pyrazolopyrimidinyl, pyrazolopyrazinyl, isoxazolopyra zinyl, oxazolopyridinyl, oxazolopyridazinyl, oxazolopyrimidinyl, Oxazolopyrazinyl, thiazolopyridinyl, thiazolopyridazinyl, iso thiazolopyrazinyl, triazolopyridinyl, triazolopyridazinyl, tria zolopyrimidinyl or triazolopyrazinyl.

Die vorstehend genannten Heterocyclylreste können beliebig sub­ stituiert sein, beispielsweise mit 1-4 gleichen oder verschie­ denen Substituenten R7, und die Heterocyclyle bedeuten bevorzugt 2-Tetrahydrofuranyl, Oxiranyl, 3-Tetrahydrofuran 1,2-Tetrahydro­ thienyl, 3-Tetrahydrothienyl, 2-Pyrrolidinyl, 3-Pyrrolidinyl, 3-Isoxazolidinyl, 4-Isoxazolidinyl, 5-Isoxazolidinyl, 3-Isothia­ zolidinyl, 4-Isothiazolidinyl, 5-Isothiazoldinyl, 3-Pyrazolidi­ nyl, 4-Pyrazolidinyl, 5-Pyrazolidinyl, 2-Oxazolidinyl, 4-Oxazolidinyl, 5-Oxazolidinyl, 2-Thiazolidinyl, 4-Thiazolidinyl, 5-Thiazolidinyl, 2-Imidazolidinyl, 4-Imidazolidinyl, 1,2,4-Oxa­ diazolidin-3-yl, 1,2,4-Oxadiazolidin-5-yl, 1,2,4-Thiadiazoli­ din-3-yl, 1,2,4-Thiadiazolidin-5-yl, 1,2,5-Triazolidin-3-yl, 1,3,4-Oxadiazolidin-2-yl, 1,3,4-Thiadiazolidin-2-yl, 1,3,4-Tria­ zolidin-2-yl, 2,3-Dihydrofur-2-yl, 2,3-Dihydrofur-3-yl, 2,5-Dihy­ drofur-2-yl, 2,5-Dihydrofur-2-yl, 2,3-Dihydrofur-3-yl, 2,3-Dihy­ drothien-2-yl, 2,3-Dihydrothien-3-yl, 2,5-Dihydrothien-2-yl, 2,5-Di-hydrothieny-2-yl, 2,4-Pyrrolin-2-yl, 2,3-Pyrrolin-3-yl, 2,5-Pyrrolin-2-yl, 2,5-Pyrrolin-3-yl, 2,3-Isoxazolin-3-yl, 3,4-Isoxazolin-3-yl, 4,5-Isoxazolin-2-yl, 2,3-Isoxazolin-4-yl, 3,4-Isoxazolin-3-yl, 4,5-Isoxazolin-4-yl, 2,3-Isoxazolin-5-yl, 3,4-Isoxazolin-5-yl, 4,5-Isoxazolin-5-yl, 2,3-Isothiazolin-3-yl, 3,4-Isothiazolin-3-yl, 4,5-Isothiazolin-3-yl, 2,3-Isothia­ zolin-4-yl, 3,4-Isothiazolin-4-yl, 4,5-Isothiazolin-4-yl, 2,3-Isothiazolin-5-yl, 3,4-Isothiazolin-5-yl, 4,5-Isothia­ zolin-5-yl, 2,3-Dihydropyrazol-1-yl, 2,3-Dihydropyrazol-2-yl, 2,3-Dihydropyrazol-3-yl, 2,3-Dihydropyrazol-4-yl, 2,3-Dihydropy­ razol-5-yl, 3,4-Dihydropyrazol-1-yl, 3,4-Dihydropyrazol-2-yl, 3,4-Dihydropyrazol-4-yl, 3,4-Dihydropyrazol-5-yl, 4,5-Dihydropy­ razol-1-yl, 4,5-Dihydropyrazol-3-yl, 4,5-Dihydropyrazol-4-yl, 4,5-Dihydropyrazol-5-yl, 3,4-Dihydrooxazol-2-yl, 2,3-Dihydro­ oxazol-3-yl, 2,3-Dihydrooxazol-4-yl, 2,3-Dihydrooxazol-5-yl, 3,-4-Dihydrooxazol-2-yl, 3,4-Dihydrooxazol-3-yl, 3,4-Dihydrooxa­ zol-4-yl, 3,4-Dihydrooxazol-5-yl, 3,4-Dihydrooxazol-2-yl, 3,4-Di­ hydrooxazol-3-yl, 3,4-Dihydrooxazol-4-yl, 2-Piperidinyl, 3-Piperidinyl, 4-Piperidinyl, 3-Tetrahydropyridazinyl, 4-Tetrah­ dropyridazinyl, 2-Tetrahydropyrimidinyl, 4-Tetrahydropyrimidinyl, 5-Tetrahydropyrimidinyl, 2-Tetrahydropyrazinyl, 1,3,5-Tetrahydro­ triazin-2-yl, 1,2,4-Tetrahydrotriazin-3-yl, 1,3-Dihydrooxa­ zin-2-yl, 1,3-Dithian-2-yl, Oxazol-2-in-2-yl, 2-Tetrahydro­ pyranyl, 1,3-Dioxolan-2-yl, Thiiazol-2-in-2-yl, 3,4,5,6-Tetrahy­ dropyridin-2-yl, 4H-1,3-Thiazin-2-yl, 4H-3,1-Benzothiazin-2-yl, 1,1-Dioxo-2,3,4,5-tetrahydrothien-2-yl, 2H-1,4-Benzothiazin-3-yl, 2H-1,4-Benzoxazin-3-yl, 1,3-Dihydrooxazin-2-yl, 1,3-Dithian-2-yl, N-Morpholinyl oder Dihydrochinazolinyl.The abovementioned heterocyclyl radicals can be substituted as desired, for example with 1-4 identical or different substituents R 7 , and the heterocyclyls preferably denote 2-tetrahydrofuranyl, oxiranyl, 3-tetrahydrofuran, 1,2-tetrahydro thienyl, 3-tetrahydrothienyl, 2- Pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazoleinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4- Oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl , 1,2,4-thiadiazoli din-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,5-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,5-dihy drofur-2-yl, 2,5-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,5 -Dihydrothia- 2-yl, 2,5-di-hydrothieny-2-yl, 2,4-pyrrolin-2-yl, 2,3-pyrrolin-3-yl, 2,5-pyrrolin-2-yl, 2,5- Pyrrolin-3-yl, 2,3-isoxazolin-3-yl, 3,4-isoxazolin-3-yl, 4,5-isoxazolin-2-yl, 2,3-isoxazolin-4-yl, 3,4- Isoxazolin-3-yl, 4,5-isoxazolin-4-yl, 2,3-isoxazolin-5-yl, 3,4-isoxazolin-5-yl, 4,5-isoxazolin-5-yl, 2,3- Isothiazolin-3-yl, 3,4-isothiazolin-3-yl, 4,5-isothiazolin-3-yl, 2,3-isothiazolin-4-yl, 3,4-isothiazolin-4-yl, 4,5 -Isothiazolin-4-yl, 2,3-isothiazolin-5-yl, 3,4-isothiazolin-5-yl, 4,5-isothiazolin-5-yl, 2,3-dihydropyrazol-1-yl, 2, 3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, 3 , 4-dihydropyrazol-2-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 3,4-dihydrooxazol-2-yl, 2,3-dihydro oxazol-3-yl, 2,3-dihydrooxazol-4-yl , 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-y l, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-di hydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 2-piperidinyl, 3-piperidinyl , 4-piperidinyl, 3-tetrahydropyridazinyl, 4-tetrahedropyridazinyl, 2-tetrahydropyrimidinyl, 4-tetrahydropyrimidinyl, 5-tetrahydropyrimidinyl, 2-tetrahydropyrazinyl, 1,3,5-tetrahydro triazin-2-yl, 1,2,4 -3-yl, 1,3-dihydrooxazin-2-yl, 1,3-dithian-2-yl, oxazol-2-in-2-yl, 2-tetrahydro pyranyl, 1,3-dioxolan-2-yl , Thiiazol-2-in-2-yl, 3,4,5,6-tetrahyropyridin-2-yl, 4H-1,3-thiazin-2-yl, 4H-3,1-benzothiazin-2-yl, 1,1-dioxo-2,3,4,5-tetrahydrothien-2-yl, 2H-1,4-benzothiazin-3-yl, 2H-1,4-benzoxazin-3-yl, 1,3-dihydrooxazin- 2-yl, 1,3-dithian-2-yl, N-morpholinyl or dihydroquinazolinyl.

Alkoxy bedeutet bevorzugt C1-C6-Alkoxy.Alkoxy preferably means C 1 -C 6 alkoxy.

Die neuen Verbindungen können beispielsweise nach folgenden Ver­ fahren hergestellt werden:The new compounds can, for example, according to the following Ver driving be manufactured:

Durch partielle Reduktion der Nitroaromaten 1 (z. B. mit Zink (analog Bamberger et al., Ann. Chem. 316 (1901), 278) oder mit Wasserstoff in Gegenwart geeigneter Katalysatoren wie z. B. Platin (analog EP 85 890)) erhält man die Hydroxylamine Z, die unter al­ kalischen Bedingungen mit Chlorkohlensäuremethylester zur Verbin­ dung 3 und anschließend mit einem Elektrophil, z. B. mit einem Al­ kylierungsmittel zu den Wirkstoffen 4 umgesetzt werden können (Schema 1).By partially reducing the nitro aromatics 1 (e.g. with zinc (analog Bamberger et al., Ann. Chem. 316 (1901), 278) or with Hydrogen in the presence of suitable catalysts such. B. platinum (Analog EP 85 890)) gives the hydroxylamines Z, which under al Kalisch conditions with chlorinated carbonate to Verbin dung 3 and then with an electrophile, e.g. B. with an Al Kylierungsmittel to the active ingredients 4 can be implemented (Scheme 1).

Außerdem kann das Hydroxylamin 5 (analog Bamberger et al., Ann. Chem. 316 (1901), 278; EP 85 890) zur Verbindung 6 alkoxyacyliert und anschließend zum Hydroxylaminether 7 alkyliert bzw. zum Hy­ droxylaminester 7 alkoxyacyliert (z. B. mit Chlorkohlensäure­ estern) werden. Die radikalische Halogenierung von 7 z. B. mit N- Bromsuccinimid, Brom, Chlor oder SO2Cl2 in Gegenwart eines Radikalstarters, z. B. Azoisobutyrodinitril oder unter Bestrahlung mit UV-Licht liefert dann das Halogenid 8 (Hal = Cl, Br; Schema 2).In addition, the hydroxylamine 5 (analogously to Bamberger et al., Ann. Chem. 316 (1901), 278; EP 85 890) can be alkoxyacylated to the compound 6 and then alkylated to the hydroxylamine ether 7 or alkoxyacylated to the hydroxylamine ester 7 (e.g. with Chlorocarbonic acid esters). The radical halogenation of 7 z. B. with N-bromosuccinimide, bromine, chlorine or SO 2 Cl 2 in the presence of a radical initiator, for. B. azoisobutyrodinitrile or under irradiation with UV light then provides the halide 8 (Hal = Cl, Br; Scheme 2).

Die Halogenide 8 können dann mit den entsprechenden Nucleophilen in die Verbindungen 9 überführt werden (Schema 3).The halides 8 can then with the corresponding nucleophiles are converted into compounds 9 (Scheme 3).

Außerdem können die Halogenide 8 radikalisch zum Dihalogenid 10 umgesetzt und anschließend mit H2O/MeOH in Gegenwart von AgNO3 in die Carbonylverbindung 11 überführt bzw. direkt mit N-Methylmor­ pholin-N-oxid zur Carbonylverbindung 11 umgesetzt werden. Außer­ dem sind aus den Halogeniden 8 die Phosphonate, Phosphoniumsalze oder Phosphinoxide 12 (P ist der jeweilige Phosphor-organische Rest) erhältlich (Schema 4).In addition, the halides 8 can be radically converted to the dihalide 10 and then converted into the carbonyl compound 11 with H 2 O / MeOH in the presence of AgNO 3 or reacted directly with N-methylmorpholine-N-oxide to the carbonyl compound 11. In addition, the halides 8 can be used to obtain the phosphonates, phosphonium salts or phosphine oxides 12 (P is the respective phosphorus-organic residue) (Scheme 4).

Die Carbonylverbindungen 11 können dann mit den entsprechenden Hydroxylaminen zu den Oximen 13 oder in einer Wittig-Reaktion zu den Olefinen 14 umgesetzt werden. Die Olefine 14 sind außerdem in einer Wittig-Reaktion ausgehend von den Phosphonaten, Phosphoni­ umsalzen bzw. Phosphinoxiden 12 erhältlich (Schema 5).The carbonyl compounds 11 can then with the corresponding Hydroxylamines to the oximes 13 or in a Wittig reaction the olefins 14 are implemented. The olefins 14 are also in a Wittig reaction based on the phosphonates, phosphoni salting or phosphine oxides 12 available (Scheme 5).

Aus den Olefinen 14 können dann durch Reduktion die gesättigten Verbindungen 15 bzw. im Fall R2=R3=H durch Halogenaddition (Hal = Cl, Br, J) und anschließender zweifacher Halogenwasserstoffab­ spaltung die Acetylene 16 hergestellt werden (Schema 6).The acetylenes 16 can then be prepared from the olefins 14 by reduction, the saturated compounds 15 or in the case R 2 = R 3 = H by halogen addition (Hal = Cl, Br, J) and subsequent double hydrogen halide elimination (Scheme 6).

Alternativ sind die Hydroxylamine Z aus den Anilinen 17, durch Bildung der Imine 18, Oxidation der Verbindungen 18 mit m-Chlor­ perbenzoesäure und Umsetzung der Oxaziridine 19 mit Hydroxylamin, erhältlich (Schema 7; analog G. Grundke et al, Synthesis 1987, 1115).Alternatively, the hydroxylamines Z from the anilines 17, through Formation of the imines 18, oxidation of the compounds 18 with m-chlorine perbenzoic acid and reaction of oxaziridines 19 with hydroxylamine, available (Scheme 7; analog G. Grundke et al, Synthesis 1987, 1115).

Die folgenden Beispiele erläutern die Herstellung der neuen Verbindungen:The following examples explain the production of the new ones Links:

Beispiel 1example 1 N-(2,6-Dimethylphenyl)-N-methoxycarbonyl-O-methyl-hydroxylamin (Tabelle 7, Nr. 1)N- (2,6-dimethylphenyl) -N-methoxycarbonyl-O-methyl-hydroxylamine (Table 7, No. 1) a) N-(2,6-Dimethylphenyl)-N-methoxycarbonyl-hydroxylamina) N- (2,6-Dimethylphenyl) -N-methoxycarbonyl-hydroxylamine

11,3 g (80 mmol) N-2,6-Dimethylphenyl-hydroxylamin (herge­ stellt analog Bamberger et al., Ann. Chem. 316 (1901), 278) und 12,5 g (90 mmol) K2CO3 in 30 ml Methylenchlorid werden bei 0-5°C tropfenweise mit 7,0 g (70 mmol) Chlorameisensäureme­ thylester versetzt. Man rührt 30 min bei 0-5°C, filtriert den unlöslichen Festkörper ab und dampft das Filtrat i. Vak. ein. Der Rückstand wird säulenchromatographisch mit Cyclohexan/Es­ sigester-Gemischen gereinigt. Man erhält 1,4 g (7,2 mmol = 9%) der Titelverbindung als dunkles Öl.
1H-NMR (CDCl3; δ in ppm): 8,85 (s, breit, 1H, OH); 7,1 (m, 3H, Phenyl); 3,75 (s, 3H, OCH3); 2,3 (s, 6H, 2×CH3) 11.3 g (80 mmol) of N-2,6-dimethylphenyl-hydroxylamine (manufactured analogously to Bamberger et al., Ann. Chem. 316 (1901), 278) and 12.5 g (90 mmol) of K 2 CO 3 7.0 g (70 mmol) of chloroformate are added dropwise in 30 ml of methylene chloride at 0-5 ° C. The mixture is stirred at 0-5 ° C. for 30 min, the insoluble solid is filtered off and the filtrate is evaporated i. Vac. a. The residue is purified by column chromatography with cyclohexane / It sigester mixtures. 1.4 g (7.2 mmol = 9%) of the title compound are obtained as a dark oil.
1 H NMR (CDCl 3 ; δ in ppm): 8.85 (s, broad, 1H, OH); 7.1 (m, 3H, phenyl); 3.75 (s, 3H, OCH 3 ); 2.3 (s, 6H, 2 × CH 3 )

b) N-(2,6-Dimethylphenyl)-N-mezhoxycarbonyl-O-methylhydroxylamin (Tabelle 7, Nr. 1)b) N- (2,6-dimethylphenyl) -N-mezhoxycarbonyl-O-methylhydroxylamine (Table 7, No. 1)

Eine Mischung von 1,4 g (7,2 mmol) N-(2,6-Dimethylphe­ nyl)-N-methoxycarbonyl-hydroxylamin (Beispiel 1a), 1,3 g (9 mmol) K2CO3 und 10 g (8 mmol) Dimethylsulfat in 10 ml Ace­ ton wird über Nacht bei Raumtemperatur gerührt. Danach wird die Reaktionsmischung mit CH2Cl2 verdünnt und mit verdünnter NH3-Lösung gerührt. Anschließend trennt man die Phasen und extrahiert die organische Phase noch zweimal mit Wasser. Die organische Phase wird über MgSO4 getrocknet und eingeengt und der Rückstand wird säulenchromatographisch mit Cyclohexan/Es­ sigester-Gemischen gereinigt. Man erhält 1,2 g (6 mmol = 83%) der Titelverbindung als farblosen Festkörper (Fp = 81°C).
1H-NMR (CDCl3; δ in ppm): 7,1 (m, 3H, Phenyl); 3,75 (s, breit, 6H, 2×OCH3); 2,3 (s, 3H, CH3).A mixture of 1.4 g (7.2 mmol) of N- (2,6-dimethylphenyl) -N-methoxycarbonyl-hydroxylamine (Example 1a), 1.3 g (9 mmol) of K 2 CO 3 and 10 g ( 8 mmol) of dimethyl sulfate in 10 ml of acetone is stirred at room temperature overnight. The reaction mixture is then diluted with CH 2 Cl 2 and stirred with dilute NH 3 solution. The phases are then separated and the organic phase is extracted twice more with water. The organic phase is dried over MgSO 4 and concentrated and the residue is purified by column chromatography with cyclohexane / It sigester mixtures. 1.2 g (6 mmol = 83%) of the title compound are obtained as a colorless solid (mp = 81 ° C.).
1 H NMR (CDCl 3 ; δ in ppm): 7.1 (m, 3H, phenyl); 3.75 (s, broad, 6H, 2x OCH 3 ); 2.3 (s, 3H, CH 3).

Entsprechend lassen sich die in den folgenden Tabellen aufgeführ­ ten Verbindungen herstellen. Die Verbindung I, Nr. 1 aus Ta­ belle 1 hat beispielsweise folgende Formel:The following tables can be listed accordingly Make connections. Compound I, No. 1 from Ta For example, belle 1 has the following formula:

Die Verbindung IV, Nr. 10 aus Tabelle 1 hat beispielsweise fol­ gende Formel:Compound IV, No. 10 from Table 1 has, for example, fol formula:

Tabelle 1 Table 1

Tabelle 2 Table 2

Tabelle 3 Table 3

Tabelle 4 Table 4

Tabelle 5 Table 5

Tabelle 6 Table 6

Tabelle 7 Table 7

Ausgewählte physikalische Daten einiger Verbindungen Selected physical data of some connections

Tabelle 8 Table 8

Die neuen Verbindungen eignen sich als Fungizide.The new compounds are suitable as fungicides.

Die neuen Verbindungen eignen sich als Fungizide.The new compounds are suitable as fungicides.

Die erfindungsgemäßen fungiziden Verbindungen bzw. die sie ent­ haltenden Mittel können beispielsweise in Form von direkt ver­ sprühbaren Lösungen, Pulvern, Suspensionen, auch hochprozentigen wäßrigen, öligen oder sonstigen Suspensionen oder Dispersionen, Emulsionen, Öldispersionen, Pasten, Stäubemitteln, Streumitteln oder Granulaten durch Versprühen, Vernebeln, Verstäuben, Ver­ streuen oder Gießen angewendet werden. Die Anwendungsformen rich­ ten sich nach den Verwendungszwecken; sie sollten in jedem Fall möglichst die feinste Verteilung der erfindungsgemäßen Wirkstoffe gewährleisten.The fungicidal compounds according to the invention or the ent holding agents can, for example, in the form of direct ver sprayable solutions, powders, suspensions, also high-proof aqueous, oily or other suspensions or dispersions, Emulsions, oil dispersions, pastes, dusts, spreading agents or granules by spraying, atomizing, dusting, ver sprinkle or pour. The application forms rich depending on the purposes; they should in any case the finest possible distribution of the active compounds according to the invention guarantee.

Normalerweise werden die Pflanzen mit den Wirkstoffen besprüht oder bestäubt oder die Samen der Pflanzen mit den Wirkstoffen be­ handelt.The plants are usually sprayed with the active ingredients or pollinated or the seeds of the plants with the active ingredients acts.

Die Formulierungen werden in bekannter Weise hergestellt, z. B. durch Verstrecken des Wirkstoff s mit Lösungsmitteln und/oder Trä­ gerstoffen, gewünschtenfalls unter Verwendung von Emulgiermitteln und Dispergiermitteln, wobei im Falle von Wasser als Verdünnungs­ mittel auch andere organische Lösungsmittel als Hilfslösungsmit­ tel verwendet werden können. Als Hilfsstoffe kommen dafür im we­ sentlichen in Betracht: Lösungsmittel wie Aromaten (z. B. Xylol), chlorierte Aromaten (z. B. Chlorbenzole), Paraffine (z. B. Erdöl­ fraktionen), Alkohole (z. B. Methanol, Butanol), Ketone (z. B. Cy­ clohexanon), Amine (z. B. Ethanolamin, Dimethylformamid) und Was­ ser; Trägerstoffe wie natürliche Gesteinsmehle (z. B. Kaoline, Tonerden, Talkum, Kreide) und synthetische Gesteinsmehle (z. B. hochdisperse Kieselsäure, Silikate); Emulgiermittel wie nichtio­ nogene und anionische Emulgatoren (z. B. Polyoxyethylen-Fettalko­ hol-Ether, Alkylsulfonate und Arylsulfonate) und Dispergiermittel wie Ligninsulfitablaugen und Methylcellulose. The formulations are prepared in a known manner, e.g. B. by stretching the active ingredient with solvents and / or Trä materials, if necessary using emulsifiers and dispersants, in the case of water as a diluent medium other organic solvents as auxiliary solution tel can be used. As auxiliaries for this come in we Considerable: solvents such as aromatics (e.g. xylene), chlorinated aromatics (e.g. chlorobenzenes), paraffins (e.g. petroleum fractions), alcohols (e.g. methanol, butanol), ketones (e.g. Cy clohexanone), amines (e.g. ethanolamine, dimethylformamide) and what ser; Carriers such as natural rock powder (e.g. kaolins, Clays, talc, chalk) and synthetic stone powder (e.g. finely divided silica, silicates); Emulsifiers such as nonio nogenic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol hol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite liquor and methyl cellulose.  

Als oberflächenaktive Stoffe kommen die Alkali-, Erdalkali-, Ammoniumsalze von aromatischen Sulfonsäuren, z. B. Lignin-, Phe­ nol-, Naphthalin- und Dibutylnaphthalinsulfonsäure, sowie von Fettsäuren, Alkyl- und Alkylarylsulfonaten, Alkyl-, Laurylether- und Fettalkoholsulfaten, sowie Salze sulfatierter Hexa-, Hepta- und Octadecanolen, sowie von Fettalkoholglykolether, Kondensati­ onsprodukte von sulfoniertem Naphthalin und seiner Derivate mit Formaldehyd, Kondensationsprodukte des Naphthalins bzw. der Naph­ thalinsulfonsäuren mit Phenol und Formaldehyd, Polyoxyethylenoc­ tylphenolether, ethoxyliertes Isooctyl-, Octyl- oder Nonylphenol, Alkylphenol-, Tributylphenylpolyglykolether, Alkylarylpolyether­ alkohole, Isotridecylalkohol, Fettalkoholethylenoxid-Kondensate, ethoxyliertes Rizinusöl, Polyoxyethylenalkylether oder Polyoxy­ propylen, Laurylalkoholpolyglykoletheracetat, Sorbitester, Li­ gnin-Sulfitablaugen oder Methylcellulose in Betracht.The alkali, alkaline earth, Ammonium salts of aromatic sulfonic acids, e.g. B. Lignin, Phe nol-, naphthalene and dibutylnaphthalenesulfonic acid, as well as Fatty acids, alkyl and alkyl aryl sulfonates, alkyl and lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols, as well as fatty alcohol glycol ethers, condensates products of sulfonated naphthalene and its derivatives Formaldehyde, condensation products of naphthalene or naphtha thalin sulfonic acids with phenol and formaldehyde, polyoxyethyleneoc tylphenol ether, ethoxylated isooctyl, octyl or nonylphenol, Alkylphenol, tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ether or polyoxy propylene, lauryl alcohol polyglycol ether acetate, sorbitol ester, Li Gnin sulfite liquor or methyl cellulose.

Pulver-, Streu- und Stäubemittel können durch Mischen oder ge­ meinsames Vermahlen der wirksamen Substanzen mit einem festen Trägerstoff hergestellt werden.Powders, materials for spreading and dusts can be mixed or mixed joint grinding of the active substances with a solid Carrier are manufactured.

Granulate, z. B. Umhüllungs-, Imprägnierungs- und Homogengranulate können durch Bindung der Wirkstoffe an feste Trägerstoffe herge­ stellt werden. Feste Trägerstoffe sind Mineralerden wie Silica­ gel, Kieselsäuren, Kieselgele, Silikate, Talkum, Kaolin, Kalk­ stein, Kalk, Kreide, Bolus, Löß, Ton, Dolomit, Diatomeenerde, Calcium- und Magnesiumsulfat, Magnesiumoxid, gemahlene Kunststof­ fe, Düngemittel, wie Ammoniumsulfat, Ammoniumphosphat, Ammonium­ nitrat, Harnstoffe und pflanzliche Produkte, wie Getreidemehl, Baumrinden-, Holz- und Nußschalenmehl, Cellulosepulver oder ande­ re feste Trägerstoffe.Granules, e.g. B. coating, impregnation and homogeneous granules can Herge by binding the active ingredients to solid carriers be put. Solid carriers are mineral earths such as silica gel, silicas, silica gels, silicates, talc, kaolin, lime stone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, Calcium and magnesium sulfate, magnesium oxide, ground plastic Fe, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, Tree bark, wood and nutshell flour, cellulose powder or other re solid carriers.

Beispiele für solche Zubereitungen sind:Examples of such preparations are:

  • I. eine Lösung aus 90 Gew.-Teilen der Verbindung aus der Ta­ belle 7, Nr. 1 und 10 Gew.-Teilen N-Methyl-a-pyrrolidon, die zur Anwendung in Form kleinster Tropfen geeignet ist;I. a solution of 90 parts by weight of the compound from Ta belle 7, No. 1 and 10 parts by weight of N-methyl-a-pyrrolidone, which is suitable for use in the form of tiny drops;
  • II. eine Mischung aus 20 Gew.-Teilen der Verbindung aus der Tabelle 7, Nr. 2, 80 Gew.-Teilen Xylol, 10 Gew.-Teilen des Anlagerungsproduktes von 8 bis 10 Mol Ethylenoxid an 1 Mol Ölsäure-N-monoethanolamid, 5 Gew.-Teilen Calciumsalz der Dodecylbenzolsulfonsäure, 5 Gew.-Teilen des Anlage­ rungsproduktes von 40 Mol Ethylenoxid an 1 Mol Ricinusöl; durch feines Verteilen der Lösung in Wasser erhält man eine Dispersion. II. A mixture of 20 parts by weight of the compound from the Table 7, No. 2, 80 parts by weight of xylene, 10 parts by weight of the Addition product of 8 to 10 moles of ethylene oxide with 1 Mol of oleic acid-N-monoethanolamide, 5 parts by weight of calcium salt the dodecylbenzenesulfonic acid, 5 parts by weight of the plant approximately 40 moles of ethylene oxide with 1 mole of castor oil; by finely distributing the solution in water a dispersion.  
  • III. eine wäßrige Dispersion aus 20 Gew.-Teilen der Verbindung der Tabelle 7, Nr. 1, 40 Gew.-Teilen Cyclohexanon, 30 Gew.-Teilen Isobutanol, 20 Gew.-Teilen des Anlagerung­ sproduktes von 40 mol Ethylenoxid an 1 mol Ricinusöl;III. an aqueous dispersion of 20 parts by weight of the compound of Table 7, No. 1, 40 parts by weight of cyclohexanone, 30 Parts by weight of isobutanol, 20 parts by weight of the addition product of 40 moles of ethylene oxide with 1 mole of castor oil;
  • IV. eine wäßrige Dispersion aus 20 Gew.-Teilen der Verbindung der Tabelle 7, Nr. 2, 25 Gew.-Teilen Cyclohexanol, 65 Gew.-Teilen einer Mineralölfraktion vom Siedepunkt 210 bis 280°C und 10 Gew.-Teilen des Anlagerungsproduktes von 40 mol Ethylenoxid an 1 mol Ricinusöl;IV. An aqueous dispersion of 20 parts by weight of the compound Table 7, No. 2, 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction with a boiling point of 210 up to 280 ° C and 10 parts by weight of the adduct of 40 moles of ethylene oxide with 1 mole of castor oil;
  • V. eine in einer Hammermühle vermahlene Mischung aus 80 Gew.-Teilen der Verbindung der Tabelle 7, Nr. 1, 3 Gew.-Teilen des Natriumsalzes der Diisobutylnaphtalin-a­ sulfonsäure, 10 Gew.-Teilen des Natriumsalzes einer Ligninsulfonsäure aus einer Sulfitablauge und 7 Gew.-Tei­ len pulverförmigem Kieselsäuregel; durch feines Verteilen der Mischung in Wasser erhält man eine Spritzbrühe;V. a mixture of 80 ground in a hammer mill Parts by weight of the compound of Table 7, No. 1, 3 Parts by weight of the sodium salt of diisobutylnaphthalene-a sulfonic acid, 10 parts by weight of the sodium salt Lignin sulfonic acid from a sulfite waste liquor and 7 parts by weight len powdered silica gel; through fine distribution a spray mixture is obtained from the mixture in water;
  • VI. eine innige Mischung aus 3 Gew.-Teilen der Verbindung der Tabelle 7, Nr. 2, 97 Gew.-Teilen feinteiligem Kaolin; dieses Stäubemittel enthält 3 Gew.-% Wirkstoff;VI. an intimate mixture of 3 parts by weight of the compound of Table 7, No. 2, 97 parts by weight of finely divided kaolin; this dust contains 3% by weight of active ingredient;
  • VII. eine innige Mischung aus 30 Gew.-Teilen der Verbindung der Tabelle 7, Nr. 1, 92 Gew.-Teilen pulverförmigem Kie­ selsäuregel und 8 Gew.-Teilen Paraffinöl, das auf die Oberfläche dieses Kieselsäuregels gesprüht wurde; diese Aufbereitung gibt dem Wirkstoff eine gute Haftfähigkeit;VII. An intimate mixture of 30 parts by weight of the compound of Table 7, No. 1, 92 parts by weight of powdered Kie silica gel and 8 parts by weight of paraffin oil, which on the Surface of this silica gel was sprayed; these Preparation gives the active ingredient good adhesion;
  • VIII. eine stabile wäßrige Dispersion aus 40 Gew.-Teilen der Verbindung der Tabelle 7, Nr. 2, 10 Gew.-Teilen des Na­ triumsalzes eines Phenolsulfonsäure-harnstoff-form­ aldehyd-Kondensates, 2 Gew.-Teilen Kieselgel und 48 Gew.-Teilen Wasser, die weiter verdünnt werden kann;VIII. A stable aqueous dispersion of 40 parts by weight of Compound of Table 7, No. 2, 10 parts by weight of Na trium salt of a phenol sulfonic acid urea form aldehyde condensate, 2 parts by weight of silica gel and 48 parts by weight of water, which can be further diluted;
  • IX. eine stabile ölige Dispersion aus 20 Gew.-Teilen der Ver­ bindung der Tabelle 7, Nr. 1, 2 Gew.-Teilen des Calcium­ salzes der Dodecylbenzolsulfonsäure, 8 Gew.-Teilen Fett­ alkohol-polyglykolether, 20 Gew.-Teilen des Natriumsalzes eines Phenolsulfonsäure-harnstoff-formaldehyd-Kondensates und 68 Gew.-Teilen eines paraffinischen Mineralöls.IX. a stable oily dispersion of 20 parts by weight of Ver Binding of Table 7, No. 1, 2 parts by weight of calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of fat alcohol-polyglycol ether, 20 parts by weight of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil.

Die neuen Verbindungen zeichnen sich durch eine hervorragende Wirksamkeit gegen ein breites Spektrum von pflanzenpathogenen Pilzen, insbesondere aus der Klasse der Ascomyceten und Basidio­ myceten, aus. Sie sind zum Teil systemisch wirksam und können als Blatt- und Bodenfungizide eingesetzt werden.The new connections are characterized by an excellent Efficacy against a wide range of plant pathogens Mushrooms, especially from the Ascomycetes and Basidio classes  mycetes, from. Some of them are systemic and can be used as Leaf and soil fungicides are used.

Besondere Bedeutung haben sie für die Bekämpfung einer Vielzahl von Pilzen an verschiedenen Kulturpflanzen wie Weizen, Roggen, Gerste, Hafer, Reis, Mais, Gras, Baumwolle, Soja, Kaffee, Zucker­ rohr, Wein, Obst- und Zierpflanzen und Gemüsepflanzen wie Gurken, Bohnen und Kürbisgewächsen, sowie an den Samen dieser Pflanzen.They are particularly important for combating a large number of mushrooms on various crops such as wheat, rye, Barley, oats, rice, corn, grass, cotton, soy, coffee, sugar pipe, wine, fruit and ornamental plants and vegetables such as cucumbers, Beans and pumpkin plants, as well as on the seeds of these plants.

Die Verbindungen werden angewendet, indem man die Pilze oder die vor Pilzbefall zu schützenden Saatgüter, Pflanzen, Materialien oder den Erdboden mit einer fungizid wirksamen Menge der Wirk­ stoffe behandelt.The compounds are applied by using the mushrooms or the Seeds, plants, materials to be protected from fungal attack or the soil with a fungicidally effective amount of the active fabrics treated.

Die Anwendung erfolgt vor oder nach der Infektion der Materia­ lien, Pflanzen oder Samen durch die Pilze.It is used before or after infection of the materia lien, plants or seeds through the mushrooms.

Speziell eignen sich die Verbindungen I zur Bekämpfung folgender Pflanzenkrankheiten:
Erysiphe graminis (echter Mehltau) in Getreide,
Erysiphe cichoracearum und Sphaerotheca fuliginea an Kürbisge­ wächsen,
Podosphaera leucotricha an Äpfeln,
Uncinula necator an Reben,
Puccinia-Arten an Getreide,
Rhizoctonia-Arten an Baumwolle und Rasen,
Ustilago-Arten an Getreide und Zuckerrohr,
Venturia inaequalis (Schorf) an Äpfeln,
Helminthosporium-Arten an Getreide,
Septoria nodorum an Weizen,
Botrytis cinerea (Grauschimmel) an Erdbeeren, Reben, Cercospora arachidicola an Erdnüssen,
Pseudocercosporella herpotrichoides an Weizen, Gerste, Pyricularia oryzae an Reis,
Phytophthora infestans an Kartoffeln und Tomaten,
Fusarium- und Verticillium-Arten an verschiedenen Pflanzen,
Plasmopara viticola an Reben,
Alternaria-Arten an Gemüse und Obst.The compounds I are particularly suitable for controlling the following plant diseases:
Erysiphe graminis (powdery mildew) in cereals,
Erysiphe cichoracearum and Sphaerotheca fuliginea on pumpkin,
Podosphaera leucotricha on apples,
Uncinula necator on vines,
Puccinia species on cereals,
Rhizoctonia species on cotton and lawn,
Ustilago species on cereals and sugar cane,
Venturia inaequalis (scab) on apples,
Helminthosporium species on cereals,
Septoria nodorum on wheat,
Botrytis cinerea (gray mold) on strawberries, vines, Cercospora arachidicola on peanuts,
Pseudocercosporella herpotrichoides on wheat, barley, Pyricularia oryzae on rice,
Phytophthora infestans on potatoes and tomatoes,
Fusarium and Verticillium species on different plants,
Plasmopara viticola on vines,
Alternaria species in vegetables and fruits.

Die neuen Verbindungen können auch im Materialschutz (Holzschutz) eingesetzt werden, z. B. gegen Paecilomyces variotii.The new connections can also be used in material protection (wood protection) are used, e.g. B. against Paecilomyces variotii.

Die fungiziden Mittel enthalten im allgemeinen zwischen 0,1 und 95, vorzugsweise zwischen 0,5 und 90 Gew.% Wirkstoff. The fungicidal compositions generally contain between 0.1 and 95, preferably between 0.5 and 90% by weight of active ingredient.  

Die Aufwandmengen liegen je nach Art des gewünschten Effektes zwischen 0,02 und 3 kg Wirkstoff pro ha.The application rates depend on the type of effect desired between 0.02 and 3 kg of active ingredient per ha.

Bei der Saatgutbehandlung werden im allgemeinen Wirkstoffmengen von 0,001 bis 50 g, vorzugsweise 0,01 bis 10 g je Kilogramm Saat­ gut benötigt.When treating seeds, amounts of active ingredient are generally used from 0.001 to 50 g, preferably 0.01 to 10 g per kilogram of seed well needed.

Die erfindungsgemäßen Mittel können in der Anwendungsform als Fungizide auch zusammen mit anderen Wirkstoffen vorliegen, der z. B. mit Herbiziden, Insektiziden, Wachstumsregulatoren, Fungizi­ den oder auch mit Düngemitteln.The agents according to the invention can be used as Fungicides are also present together with other active ingredients e.g. B. with herbicides, insecticides, growth regulators, fungicides that or with fertilizers.

Beim Vermischen mit Fungiziden erhält man dabei in vielen Fällen eine Vergrößerung des fungiziden Wirkungsspektrums.When mixed with fungicides you get in many cases an increase in the fungicidal spectrum of activity.

Die folgende Liste von Fungiziden, mit denen die erfindungsge­ mäßen Verbindungen gemeinsam angewendet werden können, soll die Kombinationsmöglichkeiten erläutern, nicht aber einschränken:
Schwefel,
Dithiocarbamate und deren Derivate, wie Ferridimethyldithiocarbamat,
Zinkdimethyldithiocarbamat,
Zinkethylenbisdithiocarbamat,
Manganethylenbisdithiocarbamat,
Mangan-Zink-ethylendiamin-bis-dithiocarbamat,
Tetramethylthiuramdisulfide,
Ammoniak-Komplex von Zink-(N,N-ethylen-bis-dithiocarbamat),
Ammoniak-Komplex von Zink-(N,N′-propylen-bis-dithiocarbamat),
Zink-(N,N′-propylen-bis-dithiocarbamat),
N,N-Polypropylen-bis-(thiocarbamoyl)-disulfid;
Nitroderivate, wie
Dinitro-(1-methylheptyl)-phenylcrotonat,
2-sec-Butyl-4,6-dinitrophenyl-3,3-dimethylacrylat,
2-sec-Butyl-4,6-dinitrophenyl-isopropylcarbonat,
5-Nitro-isophthalsäure-di-isopropylester;
heterocyclische Substanzen, wie
2-Heptadecyl-2-imidazolin-acetat,
2,4-Dichlor-6-(o-chloranilino)-s-triazin,
O,O-Diethyl-phthalimidophosphonothioat,
5-Amino-1-βbis-(dimethylamino)-phosphinyl′-3-phenyl-1,2,4-tria­ zol,
2,3-Dicyano-1,4-dithioanthrachinon,
2-Thio-1,3dithioloβ4,5-b′chinoxalin,
1-(Butylcarbamoyl)-2-benzimidazol-carbaminsäuremethylester,
2-Methoxycarbonylamino-benzimidazol,
2-(Furyl-(2))-benzimidazol,
2-(Thiazolyl-(4))-benzimidazol,
N-(1,1,2,2-Tetrachlorethylthio)-tetrahydrophthalimid,
N-Trichlormethylthio-tetrahydrophthalimid,
N-Trichlormethylthio-phthalimid,
N-Dichlorfluormethylthio-N′,N′-dimethyl-N-phenyl-schwefelsäure­ diamid,
5-Ethoxy-3-trichlormethyl-1,2,3-thiadiazol,
2-Rhodanmethylthiobenzthiazol,
1,4-Dichlor-2,5-dimethoxybenzol,
4-(2-Chlorphenylhydrazono)-3-methyl-5-isoxazolon,
Pyridin-2-thio-1-oxid,
8-Hydroxychinolin bzw. dessen Kupfersalz,
2,3-Dihydro-5-carboxanilido-6-methyl-1,4-oxathiin,
2,3-Dihydro-5-carboxanilido-6-methyl-1,4-oxathiin-4,4-dioxid,
2-Methyl-5,6-dihydro-4H-pyran-3-carbonsäure-anilid,
2-Methyl-furan-3-carbonsäureanilid,
2,5-Dimethyl-furan-3-carbonsäureanilid,
2,4,5-Trimethyl-furan-3-carbonsäureanilid,
2,5-Dimethyl-furan-3-carbonsäurecyclohexylamid,
N-Cyclohexyl-N-methoxy-2,5-dimethyl-furan-3-carbonsäureamid,
2-Methyl-benzoesäure-anilid,
2-Iod-benzoesäure-anilid,
N-Formyl-N-morpho lin-2,2,2-trichlorethylacetal,
Piperazin-1,4-diylbis-(1-(2,2,2-trichlor-ethyl)-formamid,
1-(3,4-Dichloranilino)-1-formylamin-2,2,2-trichlorethan,
2,6-Dimethyl-N-tridecyl-morpholin bzw. dessen Salze,
2,6-Dimethyl-N-cyclododecyl-morpholin bzw. dessen Salze,
N-[3-(p-tert.-Butylphenyl)-2-methylpropyl]-cis-2,6-dimethylmor­ pholin,
N-[3-(p-tert.-Butylphenyl)-2-methylpropyl)-piperidin,
1-[2-(2,4-Dichlorphenyl)-4-ethyl-1,3-dioxolan-2-yl­ ethyl)-1H-1,2,4-triazol
1-[2-(2,4-Dichlorphenyl)-4-n-pr opyl-1,3-dioxolan-2-yl­ ethyl]-1H-1,2,4-triazol
N-(n-Propyl)-N-(2,4,6-trichlorphenoxyethyl)-N′-imidazol-yl-harn­ stoff,
1-(4-Chlorphenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-buta­ non,
α-(2-Chlorphenyl)-α-(4-chlorphenyl)-5-pyrimidi n-methanol,
5-Butyl-2-dimethylamino-4-hydroxy-6-methyl-pyrimidin,
Bis-(p-chlorphenyl)-3-pyridinmethanol,
1,2-Bis-(3-ethoxycarbonyl-2-thioureido)-benzol,
1,2-Bis-83-methoxycarbonyl-2-thioureido)-benzol,
sowie verschiedene Fungizide, wie
Dodecylguanidinacetat,
3-[3-(3,5-Dimethyl-2-oxycyclohexyl)-2-hydroxyethyl)]glutarimid,
Hexachlorbenzol,
DL-Methyl-N-(2,6-dimethyl-phenyl)-N-furoyl(2)-alaninat,
DL-N-(2,6-Dimethyl-phenyl)-N-(2′-methoxyacetyl)-alanin­ methylester,
N-(2, 6-Dimethylphenyl)-N-chloracetyl-D,L-2-aminobutyrolacton,
DL-N-(2,6-Dimethylphenyl)-N-(phenylacetyl)-alaninmethylester,
5-Methyl-5-vinyl-3-(3,5-dichlorphenyl)-2,4-dioxo-1,3-oxazolidin,
3-[3,5-Dichlorphenyl(-5-methyl-5-methoxymethyl]-1,3-oxazo li­ din-2,4-dion,
3-(3,5-Dichlorhenyl)-1-isopropylcarbamoylhydantoin,
N-(3,5-Dichlorphenyl)-1,2-dimethylcyclopropan-1,2-dicarbonsäurei­ mid,
2-Cyano-[N-(ethylaminocarbonyl)-2-methoximino]-acetamid,
1-[2-(2,4-Dichlorphenyl)-pentyl]-1H-1,2,4triazol,
2,4-Difluor-α-(1H-1,2,4-triazolyl-1-methyl)-benzhydrylalkohol,
N-(3-Chlor-2,6-dinitro-4-trifluormethyl-phenyl)-5-trifluorme­ thyl-3-chlor-2-aminopyridin,
1-((bis-(4-Fluorphenyl)-methylsilyl)-methyl)-1H-1,2,4-triazol.The following list of fungicides with which the compounds according to the invention can be used together is intended to explain, but not to limit, the possible combinations:
Sulfur,
Dithiocarbamates and their derivatives, such as ferridimethyldithiocarbamate,
Zinc dimethyldithiocarbamate,
Zinc ethylene bisdithiocarbamate,
Manganese ethylene bisdithiocarbamate,
Manganese-zinc-ethylenediamine-bis-dithiocarbamate,
Tetramethylthiuram disulfide,
Ammonia complex of zinc (N, N-ethylene-bis-dithiocarbamate),
Ammonia complex of zinc (N, N'-propylene-bis-dithiocarbamate),
Zinc (N, N'-propylene-bis-dithiocarbamate),
N, N-polypropylene bis (thiocarbamoyl) disulfide;
Nitroderivatives, such as
Dinitro- (1-methylheptyl) phenylcrotonate,
2-sec-butyl-4,6-dinitrophenyl-3,3-dimethylacrylate,
2-sec-butyl-4,6-dinitrophenyl-isopropyl carbonate,
5-nitro-isophthalic acid di-isopropyl ester;
heterocyclic substances, such as
2-heptadecyl-2-imidazoline acetate,
2,4-dichloro-6- (o-chloroanilino) -s-triazine,
O, O-diethyl phthalimidophosphonothioate,
5-amino-1-βbis- (dimethylamino) -phosphinyl'-3-phenyl-1,2,4-triazole,
2,3-dicyano-1,4-dithioanthraquinone,
2-thio-1,3dithioloβ4,5-b'quinoxaline,
1- (butylcarbamoyl) -2-benzimidazole-carbamic acid methyl ester,
2-methoxycarbonylamino-benzimidazole,
2- (furyl- (2)) - benzimidazole,
2- (thiazolyl- (4)) - benzimidazole,
N- (1,1,2,2-tetrachloroethylthio) tetrahydrophthalimide,
N-trichloromethylthio-tetrahydrophthalimide,
N-trichloromethylthio-phthalimide,
N-dichlorofluoromethylthio-N ′, N′-dimethyl-N-phenylsulfuric acid diamide,
5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole,
2-rhodanmethylthiobenzthiazole,
1,4-dichloro-2,5-dimethoxybenzene,
4- (2-chlorophenylhydrazono) -3-methyl-5-isoxazolone,
Pyridine-2-thio-1-oxide,
8-hydroxyquinoline or its copper salt,
2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiine,
2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiin-4,4-dioxide,
2-methyl-5,6-dihydro-4H-pyran-3-carboxylic acid anilide,
2-methyl-furan-3-carboxylic acid anilide,
2,5-dimethyl-furan-3-carboxylic acid anilide,
2,4,5-trimethyl-furan-3-carboxylic acid anilide,
2,5-dimethyl-furan-3-carboxylic acid cyclohexylamide,
N-cyclohexyl-N-methoxy-2,5-dimethyl-furan-3-carboxamide,
2-methylbenzoic acid anilide,
2-iodo-benzoic acid anilide,
N-formyl-N-morpholine-2,2,2-trichloroethyl acetal,
Piperazin-1,4-diylbis- (1- (2,2,2-trichloro-ethyl) -formamide,
1- (3,4-dichloroanilino) -1-formylamine-2,2,2-trichloroethane,
2,6-dimethyl-N-tridecyl-morpholine or its salts,
2,6-dimethyl-N-cyclododecyl-morpholine or its salts,
N- [3- (p-tert-butylphenyl) -2-methylpropyl] cis-2,6-dimethylmorpholine,
N- [3- (p-tert-butylphenyl) -2-methylpropyl) piperidine,
1- [2- (2,4-dichlorophenyl) -4-ethyl-1,3-dioxolan-2-yl ethyl) -1H-1,2,4-triazole
1- [2- (2,4-dichlorophenyl) -4-n-propyl-1,3-dioxolan-2-yl ethyl] -1H-1,2,4-triazole
N- (n-propyl) -N- (2,4,6-trichlorophenoxyethyl) -N'-imidazol-yl urea,
1- (4-chlorophenoxy) -3,3-dimethyl-1- (1H-1,2,4-triazol-1-yl) -2-buta non,
α- (2-chlorophenyl) -α- (4-chlorophenyl) -5-pyrimidi n-methanol,
5-butyl-2-dimethylamino-4-hydroxy-6-methyl-pyrimidine,
Bis- (p-chlorophenyl) -3-pyridinemethanol,
1,2-bis (3-ethoxycarbonyl-2-thioureido) benzene,
1,2-bis-83-methoxycarbonyl-2-thioureido) benzene,
as well as various fungicides, such as
Dodecylguanidine acetate,
3- [3- (3,5-dimethyl-2-oxycyclohexyl) -2-hydroxyethyl)] glutarimide,
Hexachlorobenzene,
DL-methyl-N- (2,6-dimethyl-phenyl) -N-furoyl (2) alaninate,
DL-N- (2,6-dimethylphenyl) -N- (2'-methoxyacetyl) alanine methyl ester,
N- (2,6-dimethylphenyl) -N-chloroacetyl-D, L-2-aminobutyrolactone,
DL-N- (2,6-dimethylphenyl) -N- (phenylacetyl) alanine methyl ester,
5-methyl-5-vinyl-3- (3,5-dichlorophenyl) -2,4-dioxo-1,3-oxazolidine,
3- [3,5-dichlorophenyl (-5-methyl-5-methoxymethyl] -1,3-oxazoline-2,4-dione,
3- (3,5-dichlorhenyl) -1-isopropylcarbamoylhydantoin,
N- (3,5-dichlorophenyl) -1,2-dimethylcyclopropane-1,2-dicarboxylic acid i mid,
2-cyano- [N- (ethylaminocarbonyl) -2-methoximino] acetamide,
1- [2- (2,4-dichlorophenyl) pentyl] -1H-1,2,4triazole,
2,4-difluoro-α- (1H-1,2,4-triazolyl-1-methyl) -benzhydryl alcohol,
N- (3-chloro-2,6-dinitro-4-trifluoromethyl-phenyl) -5-trifluoromethyl-3-chloro-2-aminopyridine,
1 - ((bis- (4-Fluorophenyl) methylsilyl) methyl) -1H-1,2,4-triazole.

Claims (20)

1. Verbindung der Formel I in der die Substituenten die folgenden Bedeutungen haben:
X und Y bedeuten unabhängig voneinander F, Cl, Br, CF3, CN, NO2, Alkoxy, Alkenyloxy, Alkinyloxy, Alkyl, Alkenyl oder Alkinyl oder können zusammen zu einem ggf. substituierten aromatischen oder heteroaromatischen, alicyclischen oder heterocyclischen, partiell oder vollständig hydrierten Ring kondensiert sein, oder Y bedeutet Wasserstoff
R1 kann ggf. substituiert sein und bedeutet Alkyl, Alkenyl, Alkinyl, Cycloalkyl, Cycloalkenyl oder -CO2-Alkyl
A bedeutet -O-, -S-, -CR2=CR3-, CHR2-O-, -CHR2-S-, -CHR2-O-N=C (R4)-, -CR2=N-O-, -O-N=C(R4)-, -C≡C-, -CHR2-CHR3-, -CHR2-O-CO-, -O-CHR2- oder eine Einfachbindung,
B kann ggf. substituiert sein und bedeutet Alkyl, Alkenyl, Alkinyl, Cycloalkyl, Cycloalkenyl, Cycloalkinyl, Aryl, Hetaryl, Heterocyclyl oder Wasserstoff,
R2 und R3 bedeuten unabhängig voneinander Wasserstoff, Alkyl, Alkenyl, Alkinyl oder Cycloalkyl und R4 bedeutet Wasserstoff, Cyano, Alkyl, Alkenyl, Alkinyl, Cycloalkyl oder Alkoxy, und seine pflanzenverträglichen Säureadditionsprodukte und Base­ nadditionsprodukte, 2. Verbindung der Formel II in der A, B, und R1 die in Anspruch 1 genannte Bedeutung be­ sitzen und X und Y unabhängig voneinander F, Cl, Br, C1-C4-Al­ kyl, C1-C4-Alkoxy oder Cyano bedeuten.1. Compound of formula I. in which the substituents have the following meanings:
X and Y independently of one another are F, Cl, Br, CF 3 , CN, NO 2 , alkoxy, alkenyloxy, alkynyloxy, alkyl, alkenyl or alkynyl or can together to form an optionally substituted aromatic or heteroaromatic, alicyclic or heterocyclic, partially or completely hydrogenated ring must be condensed, or Y means hydrogen
R 1 can optionally be substituted and means alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl or -CO 2 alkyl
A means -O-, -S-, -CR 2 = CR 3 -, CHR 2 -O-, -CHR 2 -S-, -CHR 2 -ON = C (R 4 ) -, -CR 2 = NO- , -ON = C (R 4 ) -, -C≡C-, -CHR 2 -CHR 3 -, -CHR 2 -O-CO-, -O-CHR 2 - or a single bond,
B can optionally be substituted and means alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, aryl, hetaryl, heterocyclyl or hydrogen,
R 2 and R 3 independently of one another are hydrogen, alkyl, alkenyl, alkynyl or cycloalkyl and R 4 is hydrogen, cyano, alkyl, alkenyl, alkynyl, cycloalkyl or alkoxy, and its plant-compatible acid addition products and base addition products, 2nd compound of the formula II in which A, B and R 1 have the meaning given in claim 1 and X and Y independently of one another are F, Cl, Br, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or cyano. 3. Verbindung der Formel II gemäß Anspruch 2, in der Y Wasser­ stoff bedeutet.3. A compound of formula II according to claim 2, in which Y is water fabric means. 4. Verbindung der Formel III in der R1, X, Y und B die in Anspruch 1 genannte Bedeutung besitzen.4. Compound of formula III in which R 1 , X, Y and B have the meaning given in claim 1. 5. Verbindung der Formel IV in der R1,X, Y und B die in Anspruch 1 genannte Bedeutung be­ sitzen.5. Compound of formula IV in which R 1 , X, Y and B have the meaning given in claim 1. 6. Verbindung der Formel V in der R1, X, Y und B die in Anspruch 1 genannte Bedeutung be­ sitzen.6. Compound of formula V in which R 1 , X, Y and B have the meaning given in claim 1. 7. Verbindung der Formel XII in der R1, X, Y und B die in Anspruch 1 genannte Bedeutung be­ sitzen.7. Compound of formula XII in which R 1 , X, Y and B have the meaning given in claim 1. 8. Verbindung der Formel III gemäß Anspruch 4, in der Y Wasser­ stoff bedeutet.8. A compound of formula III according to claim 4, in which Y is water fabric means. 9. Zwischenprodukt der Formel VI in der X, Y, R1 und R2 die in Anspruch 1 genannte Bedeutung besitzen und Hal Halogen bedeutet. 9. Intermediate of formula VI in which X, Y, R 1 and R 2 have the meaning given in Claim 1 and Hal is halogen. 10. Zwischenprodukt der Formel VII in der X, Y, R1 und R2 die in Anspruch 1 genannte Bedeutung besitzen.10. Intermediate of formula VII in which X, Y, R 1 and R 2 have the meaning given in claim 1. 11. Zwischenprodukt der Formel VIII in der X, Y, A, B und R1 die in Anspruch 1 genannte Bedeutung besitzen.11. Intermediate of formula VIII in which X, Y, A, B and R 1 have the meaning given in claim 1. 12. Zwischenprodukt der Formel XIII 12. Intermediate of formula XIII 13. Zwischenprodukt der Formel XIV in der A, B, X und Y die in Anspruch 1 genannte Bedeutung be­ sitzen.13. Intermediate of formula XIV in which A, B, X and Y have the meaning given in claim 1. 14. Verfahren zur Herstellung einer Verbindung der Formel I, ge­ mäß Anspruch 1 dadurch gekennzeichnet, daß man ein Hydroxyl­ amin der Formel IX in der X, Y, A und B die in Anspruch 1 genannte Bedeutung be­ sitzen, unter alkalischen Bedingungen mit einem Elektrophil umsetzt.14. A process for the preparation of a compound of formula I, according to claim 1, characterized in that a hydroxyl amine of formula IX in which X, Y, A and B have the meaning given in claim 1, reacted with an electrophile under alkaline conditions. 15. Verfahren zur Herstellung einer Verbindung der Formel IX ge­ mäß Anspruch 14, dadurch gekennzeichnet, daß man ein Hydroxylamin der Formel X in der X, Y, A und B die in Anspruch 1 genannte Bedeutung be­ sitzen, mit Chlorkohlensäuremethylester umsetzt.15. A process for the preparation of a compound of formula IX according to claim 14, characterized in that a hydroxylamine of formula X. in which X, Y, A and B have the meaning given in claim 1, reacted with methyl chlorocarbonate. 16. Verfahren zur Herstellung eines Hydroxylamins der Formel X gemäß Anspruch 15 gekennzeichnet dadurch, daß man eine Nitro­ verbindung der Formel XI in der X, Y, A und B die in Anspruch 1 genannte Bedeutung be­ sitzen, reduziert.16. A process for the preparation of a hydroxylamine of the formula X according to claim 15, characterized in that a nitro compound of the formula XI in which X, Y, A and B have the meaning given in claim 1, reduced. 17. Verfahren zur Herstellung einer Verbindung der Formel I in der X, Y, R1, R2, R4 und B die in Anspruch 1 genannte Be­ deutung besitzen und A -CHR2-O-, -CHR2-S-, -CHR2-O-N=C(R4) -oder -CHR2-O-CO- bedeutet, gekennzeichnet da­ durch, daß man eine Halogenverbindung der Formel VI in der X, Y, R1 und R2 die in Anspruch 1 genannte Bedeutung besitzen und Hal Halogen bedeutet, unter alkalischen Bedin­ gungen mit einem Nucleophil umsetzt.17. Process for the preparation of a compound of formula I. in which X, Y, R 1 , R 2 , R 4 and B have the meaning given in claim 1 and A -CHR 2 -O-, -CHR 2 -S-, -CHR 2 -ON = C (R 4 ) -or -CHR 2 -O-CO-, characterized since by that a halogen compound of formula VI in which X, Y, R 1 and R 2 have the meaning given in Claim 1 and Hal means halogen, under alkaline conditions, reacted with a nucleophile. 18. Verfahren zur Herstellung einer Verbindung der Formel VI ge­ mäß Anspruch 9 dadurch gekennzeichnet, daß man eine Verbin­ dung der Formel VII in der X, Y, R1 und R2 die in Anspruch 1 genannte Bedeutung besitzen, halogeniert.18. A process for the preparation of a compound of formula VI according to claim 9, characterized in that a compound of formula VII in which X, Y, R 1 and R 2 have the meaning given in Claim 1, halogenated. 19. Verfahren zur Herstellung einer Verbindung der Formel XV in der A, B, X, Y und R1 die in Anspruch 1 genannte Bedeutung besitzen, dadurch gekennzeichnet, daß man eine Verbindung der Formel XIV gemäß Anspruch 13 unter alkalischen Bedingungen alkyliert.19. Process for the preparation of a compound of formula XV in which A, B, X, Y and R 1 have the meaning given in claim 1, characterized in that a compound of the formula XIV according to claim 13 is alkylated under alkaline conditions. 20. Fungizid, enthaltend einen inerten Trägerstoff und eine fun­ gizid wirksame Menge einer Verbindung der Formel I in der die Substituenten die folgenden Bedeutungen haben:
X und Y bedeuten unabhängig voneinander F, Cl, Br, CF3, CN, NO2, Alkoxy, Alkenyloxy, Alkinyloxy, Alkyl, Alkenyl oder Alkinyl oder können zusammen zu einem ggf. substituierten aromatischen oder heteroaromatischen, alicyclischen oder heterocyclischen, partiell oder vollständig hydrierten Ring kondensiert sein, oder Y bedeutet Wasserstoff,
R1 kann ggf. substituiert sein und bedeutet Alkyl, Alkenyl, Alkinyl, Cycloalkyl, Cycloalkenyl oder -CO2-Alkyl,
A bedeutet -O-, -S-, -CR2=CR3-, CHR2-O-, -CHR2-S-, -CHR2-O-N=C(R4)-, -CR2=N-O-, -O-N=C(R4)-, -C≡C-, -CHR2-CHR3-, -CHR2-O-CO-, -O-CHR2- oder eine Einfachbindung,
B kann ggf. substituiert sein und bedeutet Alkyl, Alkenyl, Alkinyl, Cycloalkyl, Cycloalkenyl, Cycloalkinyl, Aryl, Hetaryl, Heterocyclyl oder Wasserstoff,
R2 und R3 bedeuten unabhängig voneinander Wasserstoff, Alkyl, Alkenyl, Alkinyl oder Cycloalkyl und R4 bedeutet Wasserstoff, Cyano, Alkyl, Alkenyl, Alkinyl, Cycloalkyl oder Alkoxy oder seiner pflanzenverträglichen Säureadditionsprodukte oder Ba­ senadditionsprodukte.20. Fungicide containing an inert carrier and a fun gicidally effective amount of a compound of formula I. in which the substituents have the following meanings:
X and Y independently of one another are F, Cl, Br, CF 3 , CN, NO 2 , alkoxy, alkenyloxy, alkynyloxy, alkyl, alkenyl or alkynyl or can together to form an optionally substituted aromatic or heteroaromatic, alicyclic or heterocyclic, partially or completely hydrogenated ring must be condensed, or Y means hydrogen,
R 1 can optionally be substituted and means alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl or -CO 2 alkyl,
A means -O-, -S-, -CR 2 = CR 3 -, CHR 2 -O-, -CHR 2 -S-, -CHR 2 -ON = C (R 4 ) -, -CR 2 = NO- , -ON = C (R 4 ) -, -C≡C-, -CHR 2 -CHR 3 -, -CHR 2 -O-CO-, -O-CHR 2 - or a single bond,
B can optionally be substituted and means alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, aryl, hetaryl, heterocyclyl or hydrogen,
R 2 and R 3 independently of one another are hydrogen, alkyl, alkenyl, alkynyl or cycloalkyl and R 4 is hydrogen, cyano, alkyl, alkenyl, alkynyl, cycloalkyl or alkoxy or its plant-compatible acid addition products or base addition products. 21. Verfahren zur Bekämpfung von Pilzen, dadurch gekennzeichnet, daß man die Pilze oder die vom Pilzbefall bedrohten Pflanzen, Saatgut, Materialien oder den Erdboden behandelt mit einer fungizid wirksamen Menge einer Verbindung der Formel I in der die Substituenten die folgende Bedeutung haben:
X und Y bedeuten unabhängig voneinander F, Cl, Br, CF3, CN, NO2, Alkoxy, Alkenyloxy, Alkinyloxy, Alkyl, Alkenyl oder Alkinyl oder können zusammen zu einem ggf. substituierten aromatischen oder heteroaromatischen, alicyclischen oder heterocyclischen, partiell oder vollständig hydrierten Ring kondensiert sein, oder Y bedeutet Wasserstoff,
R1 kann ggf. substituiert sein und bedeutet Alkyl, Alkenyl, Alkinyl, Cycloalkyl, Cycloalkenyl oder -CO2-Alkyl,
A bedeutet -O-, -S-, -CR2=CR3-, CHR2-O-, -CHR2-S-, -CHR2-O-N=C(R4)-, -CR2=N-O-, -O-N=C(R4)-, -C≡C-, -CHR2-CHR3-, -CHR2-O-CO-, -O-CHR2- oder eine Einfachbindung,
B kann ggf. substituiert sein und bedeutet Alkyl, Alkenyl, Alkinyl, Cycloalkyl, Cycloalkenyl, Cycloalkinyl, Aryl, Hetaryl, Heterocyclyl oder Wasserstoff,
R2 und R3 bedeuten unabhängig voneinander Wasserstoff, Alkyl, Alkenyl, Alkinyl oder Cycloalkyl und R4 bedeutet Wasserstoff, Cyano, Alkyl, Alkenyl, Alkinyl, Cycloalkyl oder Alkoxy oder seiner pflanzenverträglichen Säureadditionsprodukte oder Ba­ senadditionsprodukte.21. A method of combating fungi, characterized in that the fungi or the plants, seeds, materials or the soil threatened by fungal attack are treated with a fungicidally effective amount of a compound of the formula I. in which the substituents have the following meaning:
X and Y independently of one another are F, Cl, Br, CF 3 , CN, NO 2 , alkoxy, alkenyloxy, alkynyloxy, alkyl, alkenyl or alkynyl or can together to form an optionally substituted aromatic or heteroaromatic, alicyclic or heterocyclic, partially or completely hydrogenated ring must be condensed, or Y means hydrogen,
R 1 can optionally be substituted and means alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl or -CO 2 alkyl,
A means -O-, -S-, -CR 2 = CR 3 -, CHR 2 -O-, -CHR 2 -S-, -CHR 2 -ON = C (R 4 ) -, -CR 2 = NO- , -ON = C (R 4 ) -, -C≡C-, -CHR 2 -CHR 3 -, -CHR 2 -O-CO-, -O-CHR 2 - or a single bond,
B can optionally be substituted and means alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, aryl, hetaryl, heterocyclyl or hydrogen,
R 2 and R 3 independently of one another are hydrogen, alkyl, alkenyl, alkynyl or cycloalkyl and R 4 is hydrogen, cyano, alkyl, alkenyl, alkynyl, cycloalkyl or alkoxy or its plant-compatible acid addition products or base addition products.
DE4234028A 1992-01-29 1992-10-09 New N-phenyl-carbamate, urea or amide derivs. Withdrawn DE4234028A1 (en)

Priority Applications (27)

Application Number Priority Date Filing Date Title
DE4234028A DE4234028A1 (en) 1992-10-09 1992-10-09 New N-phenyl-carbamate, urea or amide derivs.
AT93902227T ATE165818T1 (en) 1992-01-29 1993-01-18 CARBAMATES AND PLANT PROTECTIVE PRODUCTS CONTAINING THEM
RU94045970A RU2129118C1 (en) 1992-01-29 1993-01-18 Carbamates, intermediate compounds, a fungicide composition, a method of struggle against fungi
CZ19941785A CZ288922B6 (en) 1992-01-29 1993-01-18 Carbamates and preparations for plant protection in which the carbamates are comprised
DE59308508T DE59308508D1 (en) 1992-01-29 1993-01-18 CARBAMATE AND THESE PLANT PROTECTION PRODUCTS
NZ246603A NZ246603A (en) 1992-01-29 1993-01-18 Carbamate derivatives and fungicidal compositions thereof
DK93902227T DK0624155T4 (en) 1992-01-29 1993-01-18 Carbamates and plant protection products containing these
HU9401961A HU217905B (en) 1992-01-29 1993-01-18 Carbamates and fungicidal compositions containing them and process for their use and intermediates of carbamates
US08/256,628 US5824705A (en) 1992-01-29 1993-01-18 Carbamates and crop protection agents containing them
SK907-94A SK283351B6 (en) 1992-01-29 1993-01-18 Carbamates and plant-protecting agents containing them
BR9305817A BR9305817A (en) 1992-01-29 1993-01-18 Intermediate carbamate derived from hydroxylamine fungicidal compound and process to combat fungi
UA94085752A UA37202C2 (en) 1992-01-29 1993-01-18 carbamates, intermediary compounds, fungicide composition, a method for controlling fungi
PCT/EP1993/000104 WO1993015046A1 (en) 1992-01-29 1993-01-18 Carbamates and plant-protecting agents containing them
EP93902227A EP0624155B2 (en) 1992-01-29 1993-01-18 Carbamates and plant-protecting agents containing them
ES93902227T ES2116436T5 (en) 1992-01-29 1993-01-18 CARBAMATES AND PHYTOSANITARY AGENTS CONTAINING THESE.
KR1019940702612A KR100282840B1 (en) 1992-01-29 1993-01-18 Carbamates and crop protection products containing them
AU33514/93A AU671974B2 (en) 1992-01-29 1993-01-18 Carbamates and plant-protecting agents containing them
JP51289793A JP3883566B2 (en) 1992-01-29 1993-01-18 Carbamates and crop protection agents containing them
CA002127110A CA2127110C (en) 1992-01-29 1993-01-18 Carbamates and crop protection agents containing them
IL10448993A IL104489A (en) 1992-01-29 1993-01-22 Carbamates, intermediates for their preparation and fungicides containing them
TW82100771A TW247270B (en) 1992-10-09 1993-02-05
FI943523A FI120766B (en) 1992-01-29 1994-07-27 Carbamates and plant protection products containing them
NO942814A NO302467B1 (en) 1992-01-29 1994-07-28 Carbamates, pesticides containing them, their use and intermediates for their preparation
AU52465/96A AU680592B2 (en) 1992-01-29 1996-05-23 Compounds as intermediates
US09/110,884 US5981532A (en) 1992-01-29 1998-07-07 Carbamates and crop protection agents containing them
US09/275,767 US6075148A (en) 1992-01-29 1999-03-25 Carbamates and crop protection agents containing them
US09/527,118 US6252083B1 (en) 1992-01-29 2000-03-16 Carbamates and crop protection agents containing them

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0835865A1 (en) * 1996-10-11 1998-04-15 Rohm And Haas Company Dihydropyridazinones and pyridazinones and their use as fungicides and insecticides

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0835865A1 (en) * 1996-10-11 1998-04-15 Rohm And Haas Company Dihydropyridazinones and pyridazinones and their use as fungicides and insecticides

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