CA2100546A1 - Substituted acrylates and crop protection agents containing them - Google Patents

Substituted acrylates and crop protection agents containing them

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Publication number
CA2100546A1
CA2100546A1 CA002100546A CA2100546A CA2100546A1 CA 2100546 A1 CA2100546 A1 CA 2100546A1 CA 002100546 A CA002100546 A CA 002100546A CA 2100546 A CA2100546 A CA 2100546A CA 2100546 A1 CA2100546 A1 CA 2100546A1
Authority
CA
Canada
Prior art keywords
cycloalkenyl
substituted
alkenyl
alkynyl
alkyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
CA002100546A
Other languages
French (fr)
Inventor
Bernd Mueller
Franz Roehl
Hartmann Koenig
Hubert Sauter
Gisela Lorenz
Eberhard Ammermann
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
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Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of CA2100546A1 publication Critical patent/CA2100546A1/en
Abandoned legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/273—2-Pyrrolidones 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 other ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/734—Ethers
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/734—Ethers
    • C07C69/736—Ethers the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D211/74—Oxygen atoms
    • C07D211/76—Oxygen atoms attached in position 2 or 6
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D215/14—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • C07—ORGANIC CHEMISTRY
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    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members 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
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    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
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    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
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    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles

Abstract

BASF Aktiengesellschaft 920400 O.Z. 0050/43411 Substituted acrylates and crop protection agents containing them ABSTRACT OF THE DISCLOSURE:
Substituted acrylates of the formula I

I

where:
B is substituted alkyl, substituted alkenyl, substituted alkynyl, substituted cycloalkyl, substituted cycloalkenyl, substi-tuted cycloalkynyl, or substituted heterocyclyl, X and Y are identical or different and are hydrogen, halogen, cyano, nitro, haloalkyl, alkyl, haloal-koxy, alkenyl, alkynyl, cycloalkyl, aryl, hetaryl, heterocy-clyl, cycloalkenyl, cycloalkinyl, alkoxy, alkenyloxy, alky-nyloxy, cycloalkyloxy, aryloxy, hetaryloxy, heterocyclyloxy, cycloalkenyloxy, cycloalkynyloxy, alkoximino, alkenyloxi-mino, alkynyloximino, cycloalkyloximino, cycloalkenyloxi-mino, cycloalkynyloximino, aryloximino, hetaryloximino, het-erocyclyloximino, alkoxycarbonyl, alkenyloxycarbonyl, alky-nyloxycarbonyl, cycloalkyloxycarbonyl, aryloxycarbonyl, he-taryloxycarbonyl, heterocyclyloxycarbonyl, cycloalkenyloxy-carbonyl, cycloalkynyloxycarbonyl, alkylaminocarbonyl, dial-kylaminocarbonyl, alkenylaminocarbonyl, dialkenylaminocarbo-nyl, alkynylaminocarbonyl, dialkynylaminocarbonyl, cycloal-kylaminocarbonyl, cycloalkenylaminocarbonyl, cycloalkynyla-minocarbonyl, arylaminocarbonyl, hetarylaminocarbonyl, het-erocyclylaminocarbonyl, alkylthio, alkenylthio, alkynylthio, BASF Aktiengesellschaft 920400 O.Z. 0050/43411 cycloalkylthio, arylthio, hetarylthio, heterocyclylthio, cy-cloalkenylthio, cycloalkynylthio, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, arylamino, hetarylamino, het-erocyclylamino, cycloalkenylamino, cycloalkynylamino, alkyl-carbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbo-nyl, arylcarbonyl, hetarylcarbonyl, heterocyclylcarbonyl, cycloalkenylcarbonyl, cycloalkynylcarbonyl, alkylsulfoxyl, alkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl, aryl-sulfoxyl, hetarylsulfoxyl, heterocyclylsulfoxyl, cycloalky-nylsulfoxyl, cycloalkenylsulfoxyl, alkylsulfonyl, alkenyl-sulfonyl, alkynylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, hetarylsulfonyl, heterocyclylsulfonyl, cycloalkenylsulfonyl, cycloalkynylsulfonyl, alkylsulfinyl, alkenylsulfinyl, alky-nylsulfinyl, cycloalkylsulfinyl, arylsulfinyl, hetarylsulfi-nyl, heterocyclylsulfinyl, cycloalkenylsulfinyl, cycloalky-nylsulfinyl, alkylcarbonyloxy, alkenylcarbonyloxy, alkynyl-carbonyloxy, cycloalkylcarbonyloxy, cycloalkenylcarbonyloxy, cycloalkynylcarbonyloxy, arylcarbonyloxy, hetarylcarbony-loxy, heterocyclylcarbonyloxy, alkylcarbonylamino, alkenyl-carbonylamino, alkynylcarbonylamino, cycloalkylcarbonyla-mino, cycloalkenylcarbonylamino, cycloalkynylcarbonylamino, arylcarbonylamino, hetarylcarbonylamino, heterocyclylcarbo-nylamino, cycloalkylalkyloxy, cycloalkenylalkyloxy, cycloal-kynylalkyloxy, arylalkyloxy, hetarylalkyloxy or heterocycly-lalkyloxy, and R1 and R2 are alkyl, alkenyl, alkynyl, cycloalkyl or cy-cloalkenyl, and acid addition products and base addition products of such compounds, and fungicides containing these compounds.

Description

` ` 2100~
O.Z. 0050/43411 Substituted acryl~tes and crop protection acents containin~ them The present invention relates to sub~tituted acrylates and their use as crop protection agents, in particular for controlling fungi, insects, nematodes and spider mites.
It i8 known that acrylate~, for example methyl ~-(2-hydroxyphenyl)-~-me~hoxyacrylate (EP 251 082, EP 178 826) can be used as fungicides. However, their fungicidal action i~ unsatisfactory.
We have found, surprisingly, that sub~tituted acrylates of the formula I

X Y
B~o~ I

Rl02C oR2 where B is alkyl which is sub~tituted by 1-4 identical or different sub~tituents R3, alkenyl which i8 substituted by 1-4 identical or different ~ubstituents R4, alkynyl which i8 ~ub~titu~ed by 1-4 identical or different substit~ents R5, cycloalkyl which is sub6tituted by 1-4 identical or d:ifferent sub~tituents R6, cycloalkenyl which i8 ~ubstituted by 1-4 identical or different substituents R7, cycloalkynyl which is substituted by 1-4 identical or different sub~tituents R8 or heterocyclyl which is substituted by 1-4 identical or different substituents R9, X and Y independently of one another ~re each hydrogen, halogen, cyano, nitro, haloalkyl, alkyl, haloalkoxy, alkenyl, alkynyl, cycloalkyl, aryl, hetaryl, heterocycl-yl, cycloalkenyl, cycloal~ynyl, ~lkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, aryloxy, hetarylo~y, hetero-cyclyloxy, cycloalkenyloxy, cycloalkynyloxy, alkoximino, 21~0~46 - 2 - O.Z. 0050/43411 alkonyloximino, alkynyloximino, cycloalkyloximino, cycloalkenyloximino, cycloalkynyloximino, aryloximino, hetaryloximino, heterocyclyloximino, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, cycloalkoxy-carbonyl aryloxycarbonyl, hetaryloxycarbonyl, hetero-cyclyloxycarbonyl,cylcoalkenyloxycarbonyl,cycloalkynyl-oxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkenylaminocarbonyl, dialkenylaminocarbonyl, alkynyl-aminocarbonyl, dialkynylaminocarbonyl, cycloalkylamino carbonyl, cycloalkenylaminocarbonyl, cycloalkynylamino-carbonyl, arylaminocarbonyl, hetarylaminocarbonyl, heterocyclylaminocarbonyl, alkylthio, alkenylthio, alkynylthio, cycloalkylthio, arylthio, hetarylthio, heterocyclylthio, cycloalkenylthio, cycloalkynylthio, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, arylamino, hetarylamino, heterocyclylamino, cycloalkenyl-amino, cycloalkynylamino, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, het-arylcarbonyl,heterocyclylcarbonyl,cycloalkenylcarbonyl, cycloalkynylcarbonyl, alkylsulfoxyl, alkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl, arylsulfoxyl, hetarylsulfoxyl, heterocyclylsulfoxyl, cycloalkynyl-.. sulfoxyl, cycloalkenylsulfoxyl, alkylsulfonyl, alkenyl-sulfonyl, alkynylsulfonyl, cycloalkyl~ulfonyl, aryl-sulfonyl, hetarylsulfonyl, heterocyclylsulfonyl, cyclo-alkenylsulfonyl, cycloalkynylsulfonyl, alkylsulfinyl, alkenylsulfinyl, alkynylsulfinyl, cycloalkylsulfinyl, aryl~ulfinyl, hetarylsulfinyl, heterocyclylsulfinyl, cycloalkenylsulfinyl, cycloalkynylsulfinyl, alkyl-carbonyloxy, alkenylcarbonyloxy, alkynylcarbonyloxy,cycloalkylcarbonyloxy, cycloalkenylcarbonyloxy, cyclo-alkynylcarbonyloxy, arylcarbonyloxy, hetarylcarbonyloxy, h~terocyclylcarbonyloxy, alkylcarbonylamino, alkenyl-csrbonylamino, alkynylcarbonylamino, cycloalkylcarbonyl-amino, cycloalkenylcarbonyl~mino, cycloalkynylcarbonyl-amino, arylcarbonylamino, hetarylcarbonylamino, hetero-cyclylcarbonylamino, cycloalkylalkoxy, cycloalkenyl-210~4~
- 3 - O.~. 0050/43411 alkoxy, cylcoalkynylalkoxy, arylalkoxy, hetarylalkoxy or heterocyclylalkoxy, if X and Y are on ad~acent carbon atoms, they may be condensed to form an unsubstituted or substituted aroma-tic or heteroaromatic, alicycli~ or heterocyclic, par-tially or completely hydrogenated ring, Rl and R2 may be sub~tituted and independently of one another are each alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl, R3 and R4 may be substituted by 1-4 identi-cal or different substituents Rl, and R3 and R~ are eachnitro, alkoxy, haloalkoxy, alkynyl, cycloalkyl, hetaryl, heterocyclyl, cycloalkenyl, cycloalkynyl, alkenyloxy, alkynyloxy, cycloalkoxy, hetaryloxy, het~rocyclyloxy, cycloalkenyloxy, cycloalkynyloxy, alkoximino, alkenyl-oxLmino, alkynyloximino, cycloalkoxLmino, cycloalkenyl-oximino, cycloalkynyloximino, aryloximino, hetarylox-imino, heterocyclyloximino, cycloalkoxycarbonyl aryloxycarbonyl, hetaryloxycarbonyl, he~erocyclyloxy-carbonyl, cycloalkenyloxycarbonyl, cycloalkynyloxy-carbonyl, alkylaminocarbonyl, dialkylaminocarbonyl,alkenylaminocarbonyl, dialkenylaminocarbonyl, alkynyl-aminocarbonyl, dialkynylaminocarbonyl, cycloalkyl2mino-carbonyl, cycloalkenylaminocarbonyl, cycloalkynylamino-carbonyl, arylaminocarbonyl, hetarylaminocarbonyl, heterocyclylaminocarbonyl, alkyl~hio, alkenylthio, alkynylthio, cycloalkylthio, arylthio, hetarylthio, heterocyclylthio, cycloalkenylthio, cycloalkynylthio, alkylamino, alkenylamino, al~ynylamino, cycloalkylamino, arylamino, hetarylamino, heterocyclylamino, cycloalkenyl-amino, cycloalkynylamino, alkylcarbonyl, alkenylcarbonyl,alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, het-arylcarbonyl,heterocyclylcarbonyl,cycloalkenylcarbonyl, cycloalkynylcarbonyl, alkylsulfoxyl, alkenylsulfoxyl, cycloalkylsulfoxyl, aryl~ulfoxyl, hetarylsulfoxyl, heterocyclylsulfoxyl,cycloalkynylsulfoxyl,cycloalkenyl-sulfoxyl, alkylsulfonyl, alkenyl~ulfonyl, alkynyl-sulfonyl, cycloalkylsulfonyl, arylsulfonyl, hetaryl-2100~46 - 4 - O.Z. 0050/43411 sulfonyl, heterocyclylxulfonyl, cycloalkenylsulfonyl, cycloalkynyl~ulfonyl, alkyl~ulfinyl, alkenylsulfinyl, alkynyl~ulfinyl, cycloalkyl~ulfinyl, arylsulfinyl, hetarylsulfinyl, heterocyclylsulfinyl, cyclsalkenyl-sulfinyl, cycloalkynylsulfinyl, alkylcarbonyloxy, alkenylcarbonyloxy,alkynylcarbonyloxy,cycloalkylcarbon-yloxy, cycloalkenylcarbonyloxy, cycloalkynylcarbonyloxy, arylcarbonyloxy, hetarylcarbonyloxy, heterocyclylcarbon-yloxy, alkylcarbonylamino, alkenylcarbonylamino, alkynyl-carbonylamino, cycloalkylcarbonylamino, cycloalkenyl-carbonylamino, cycloalkynylcarbonylamino, arylcarbonyl-amino, hetarylcarbonylamino, heterocyclylcarbonylamino, cycloalkylalkoxy,cycloalkenylalkoxy,cycloalkynylalkoxy, hetarylalkoxy, heterocyclylalkoxy, alkynylalkenyl, cyclo-alkylalkenyl, cycloalkenylalkenyl, cycloalkynylalkenyl, hetarylalkenyl, heterocyclylalkenyl, alkoximinoalkyl, alkenyloxLminoalkyl, alkynyloxminoalkyl, cycloalkox-iminoalkyl, cycloalkenyloximino~lkyl, cycloalkynylox-iminoalkyl, aryloximinoalkyl, hetaryloxLminoalkyl, heterocyclyloximinoalkyl, alkoximinoalkenyl, alkenylox-iminoalkenyl, alkynyloxLminoalkenyl, cycloalkoximino-alkenyl,cycloalkenyloximinoalkenyl,cycloalkynyloxLmino-alkenyl, aryloximinoalkenyl, hetaryloximinoalkenyl or heterocyclyloxLminoalkenyl, R5, R6, R7 and R8 may be substituted by 1-4 identical or different substituents Rl, and R5, R6, R7 and R8 are each nitro, haloalkyl, alkyl, haloalkoxy, alkenyl, alkynyl, cycloalkyl, sryl, hetaryl, heterocyclyl, cycloalkenyl, cycloalkynyl, alkoxy, alkenyloxy, alkynyloxy, cyclo-alkoxy, aryloxy, hetaryloxy, heterocyclyloxy, cyclo-alkenyloxy, cycloalkynyloxy, alkoximino, alkenyloximino, alkynyloximino, cycloalkoxLmino, cycloalkenyloximins, cycloalkynyloximino, aryloximino, hetaryloximino, hetero-cyclyloximino, cycloalkoxycarbonyl, aryloxycarbonyl, het-aryloxycarbonyl,heterocyclyoxycarbonyl,cycloalkenyloxy-carbonyl, cycloalkynyloxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl/ alkenylaminocarbonyl, dialkenyl-2100.'J46 - 5 - O.Z. 0050/43411 aminocarbonyl, alkynylaminocarbonyl, dialkynylamino-carbonyl, cycloalkylaminocarbonyl, cycloalkenylamino-carbonyl, cycloalkynylaminocarbonyl, arylaminocarbonyl, hetarylaminocarbonyl, heterocyclylaminocarbonyl, alkyl-S thio, alkenylthio, alkynylthio, cycloalkylthio, arylthio, hetarylthio, heterocyclylthio, cycloalkenylthio, cyclo-alkynylthio, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, arylamino, hetarylamino, heterocyclyl-amino, cycloalkenylamino, cycloalkynylamino, alkylcarbon-yl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, hetarylcarbonyl, heterocyclylcarbonyl, cycloalkenylcarbonyl, cycloalkynylcarbonyl, alkylsulfox-yl, alkenyl~ulfoxyl, alkynylsulfoxyl, cycloalkyl~ulfoxyl, aryl 8ul foxyl, hetaryl~ulfoxyl, heterocyclyl~ulfoxyl, cycloalkynylsulfoxyl, cycloalkenyl~ulfoxyl, alkylsulfonyl, alkenyl~ulfonyl, alkynylsulfonyl, cycloalkylQulfonyl, arylsulfonyl, hetarylsulfonyl, heterocyclyl~ulfonyl, cycloalkenylsulfonyl, cycloalkynylsulfonyl, alkyl~ulfinyl, alkenyl~ulfinyl, alkynyl~ulfinyl, cycloalkyl~ulfinyl J arylsulfinyl, hetarylsulfinyl, heterocyclylsulfinyl, cycloalkenyl-sulfinyl, cycloalkynyl~ulfinyl, alkylcarbonyloxy, alkenylcarbonyloxy,~lkynylcarbonyloxy,cycloalkylcarbon-yloxy, cycloalkenylcarbonyloxy, cycloalkynylcarbonyloxy, arylcaxbonyloxy, hetarylcarbonyloxy, heterocyclylcarbon-yloxy, alkylcarbonylamino, alkenylcarbonylamino, alkynyl-carbonylamino, cycloalkylcarbonylamino, cycloalkenyl-carbonylamino, cycloalkynylcarbonylamino, arylcarbonyl-amino, hetarylcarbonylamino or heterocyclylcarbonylamino, R9 may be substituted by 1-4 identical or different substituent3 R10, and R~ i~ hydrogen, halogen, cyano, nitro, haloalkyl, alkyl, haloalkoxy, alkenyl, al~ynyl, cycloalkyl, aryl, hetaryl, heterocyclyl, cycloalkenyl, cycloalkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalk-oxy, aryloxy, hetaryloxy, heterocyclyloxy, cycloalkenyl-o~y, cycloalkynyloxy, alkoximino, alkenyloximino, alkynyloximino, cycloalkoximino, cycloalkenyloximino, 2100~6 - 6 - O.Z. 0050/43411 cycloalkynyloximino, aryloximino, hetaryloximino, hetero-cyclyloximino, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl,cycloalkoxycarbonyl,aryloxycarbonyl, hetaryloxycarbonyl, heterocyclyloxycarbonyl, cycloalkenyloxycarbonyl, cycloalkynyloxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkenylaminocarbonyl, dialkenylaminocarbonyl, alkynylaminocarbonyl, dialkynylaminocarbonyl, cycloalkylaminocarbonyl, cycloalkenylaminocarbonyl, cycloalkynylaminocarbonyl, arylaminocarbonyl, hetarylaminocarbonyl, heterocyclylaminocarbonyl, alkyl-thio, alkenylthio, alkynylthio, cycloalkylthio, arylthio, hetarylthio, heterocyclylthio, cycloalkenylthio, cyclo-alkynylthio, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, arylamino, hetarylamino, heterocyclyl-amino, cycloalkenyl~mino, cycloalkynylamino, alkylcarbon-yl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, hetarylcarbonyl, heterocyclylcarbonyl, cycloalkenylcarbonyl, cycloalkynylcarbonyl, alkylsulfox-yl, alkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl, aryl6ulfoxyl, hetarylsulfoxyl, heterocyclylsulfoxyl, cycloalkynylsulfoxyl, cycloalkenylsulfoxyl, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, cycloalkylsulfonyl, aryl~ulfonyl, hetarylsulfonyl, heterocyclylsulfonyl, cycloalkenylsulfonyl, cycloaIkynylsulfonyl, alkylsulfinyl, alkenylsulfinyl, alkynyl~ulfinyl, cycloalkylsulfinyl, arylsulfinyl, hetarylsulfinyl, heterocyclylsulfinyl, cycloalkenyl-sulfinyl, cycloalkynylsulfinyl, alkylsulfinyl, alkenyl~ulfinyl, alkynyl~ulfinyl, cycloalkylsulfinyl, arylsulfinyl, hetarylsulfinyl, heterocyclylsulfinyl, cycloalkenylsulfinyl, cycloalkynylsulfinyl, alkyl-carbonyloxy, alkenylcarbonyloxy, alkynylcarbonyloxy, cycloalkylcarbonyloxy, cycloalkenylcarbonyloxy, cyclo-alkynylcarbonyloxy, arylcarbonyloxy, hetarylcarbonyloxy, heterocyclylcarbonyloxy, alkylcarbonylamino, alkenyl-carbonylamino, alkynylcarbonylamino, cycloalkylcarbonyl-2100~46 - 7 - O.Z. 0050/43411 amino, cycloalkenylcarbonylamino, cycloalkynylcarbonyl-amino, arylcarbonylamino, hetarylcarbonylamino, hetero-cyclylcarbonylamino, cycloalkylalkoxy, cycloalkenylalkoxy, cycloalkynylalkoxy, arylalkoxy, hetarylalkoxy or heterocyclylalkoxy, Rl may be substituted by 1-4 identical or different substituent~ R11, and Rl is hydrogen, halogen, cyano, nitro, haloalkyl, alkyl, haloalkoxy, alkenyl, alkynyl, cycloalkyl, aryl, hetaryl, heterocyclyl, cycloalkenyl, cycloalkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalk-oxy, aryloxy, hetaryloxy, heterocyclyloxy, cycloalkenyl-oxy, cycloalkynyloxy, alkoximino, alkenyloximino, alkynyloximino, cycloalkoximino, cycloalkenyloximino, cycloalkynyloximino, aryloximino, hetaryloximino, hetero-cyclyloximino, alkoxycarbonyl, alkenyloxycarbonyl,alkynyloxycarbonyl,cycloalkoxycarbonyl,aryloxycarbonyl, hetaryloxycarbonyl, heterocyclyloxycarbonyl, cycloalkenyloxycarbonyl, cycloalkynyloxycarbonyl, alkylaminocarbonyl, dialkyl2~minocarbonyl, alkenylaminocarbonyl, dialkenylaminocarbonyl, alkynylaminocarbonyl, dialkynylaminocarbonyl, cycloalkylaminoc~rbonyl, cycloalkenylaminocarbonyl, -- cycloalkynylaminocarbonyl, arylaminocarbonyl, hetaryl~minocnrbonyl, heterocyclylaminocarbonyl, alkyl-thio, ~lkenylthio, alkynylthio, cycloalkylthio, arylthio, hetaryithio, heterocyclylthio, cycloalkenylthio, cyclo-slkynylthio, alkylamino, alkenylamino, alkynylamino, cycloslkylamino, arylamino, hetarylamino, heterocyclyl-smino, cycloalkenylamino, cyclo~lkynylamino, alkylcarbon-yl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, arylc~rbonyl, hetarylcarbonyl, heterocyclylcarbonyl, cycloalkenylcarbonyl, cycloalkynylcarbonyl, alkyl~ulfox-yl, hlkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl, arylsulfoxyl, hetaryl ulfoxyl, heterocyclylsulfoxyl, cycloalkynylsulfoxyl, cycloalkenylsulfoxyl, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, hetaryl~ulfonyl, `- 2iO0546 - 8 - O.Z. 0050/43411 heterocyclyl~ulfonyl, cycloalkenylsulfonyl, cycloalkynylsulfonyl, alkylsulfinyl, alkenyl 8ul finyl, alkynylsulfinyl, cycloalkylsulfinyl, arylsulfinyl, hetarylsulfinyl, heterocyclylsulfinyl, cycloalkenyl-S sulfinyl, cycloalkynylsulfinyl, alkylcarbonyloxy,alkenylcarbonyloxy,alkynylcarbonyloxy,cycloalkylcarbon-yloxy, cycloalkenylcarbonyloxy, cycloalkynylcarbonyloxy, arylcarbonyloxy, hetarylcarbonyloxy, heterocyclylcarbon-yloxy, alkylcarbonylamino, alkenylcarbonylamino, alkynyl-carbonylamino, cycloalkylcarbonylamino, cycloalkenyl-carbonylamino, cycloalkynylcarbonylamino, arylcarbonyl-amino, hetarylcarbonylamino, heterocyclylcarbonylamino, cycloalkylalkoxy,cycloalkenylalkoxy,cycloalkynylalkoxy, arylalkoxy, hetarylalkoxy or heterocyclylalkoxy, R1l may be substituted and is hydrogen, halo~en, cyano, nitro, haloalkyl, alkyl, haloalkoxy, alkenyl, alkynyl, cycloalkyl, aryl, hetaryl, heterocyclyl, cycloalkenyl, cycloalkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalk-oxy, aryloxy, hetaryloxy, heterocyclyloxy, cycloalkenyl-oxy, cycloalkynyloxy, alkoximino, alkenyloximino,alkynyloximino, cycloalkyloximino, cycloalkenyloximino, cycloalkynyloximino, aryloximino, hetaryloximino, hetero-cyclyloximino, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl,cycloalkoxycarbonyl,aryloxycarbonyl, hetaryloxycarbonyl, heterocyclyloxycarbonyl, cycloaïkenyloxycarbonyl, cycloalkynyloxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkenylaminocarbonyl, dialkenylaminocarbonyl, alkynylaminocarbonyl, dialkynylaminocarbonyl, cycloalkylaminocarbonyl, cycloalkenylaminocarbonyl, cycloalkynylaminocarbonyl, arylaminocarbonyl, hetarylaminocarbonyl, heterocyclyl~minocarbonyl, alkyl-thio, alkenylthio, alkynylthio, cycloalkylthio, arylthio, hetarylthio, heterocyclylthio, cycloalkenylthio, cyclo-alkynylthio, alkylamino, alkenylamino, alkynylamino,cycloalkylamino, arylamino, hetarylamino, heterocyclyl-amino, cycloalkenylamino, cycloalkynylamino, alkyl-210~4~
- 9 - O.Z. 0050/43411 càrbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, hetarylcarbonyl, heterocyclylcarbonyl, cycloalkenylcarbonyl, cycloalkynylcarbonyl, alkyl~ulfoxyl, alkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl, arylsulfoxyl, hetarylsulfoxyl, heterocyclyl~ulfoxyl, cycloalkynylsulfoxyl, cycloalkenylsulfoxyl, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, hetaryl~ulfonyl, he~erocyclylsulfonyl, cycloalkenylsulfonyl, cycloalkynylsulfonyl, alkylsulfinyl, alkenylsulfinyl, alkynyl~ulfinyl, ~ycloalkylsulfinyl, axylsulfinyl, hetarylsulfinyl, heterocyclylsulfinyl, cycloalkenyl-sulfinyl, cycloalkynyl~ulfinyl, alkylcarbonyloxy, alkenylcarbonyloxy,alkynylcarbonyloxy,cycloalkylcarbon-yloxy, cycloalkenylcarbonyloxy, cycloalkynylcarbonyloxy, arylcarbonyloxy, hetarylcarbonyloxy, heterocyclylcarbon-yloxy, alkylcarbonylamino, alkenylcarbonylamino, alkynyl-carbonylamino, cycloalkylcarbonylamino, cycloalkenyl-carbonylamino, cycloalkynylcarbonylamino, arylcarbonyl-amino, hetarylcarbonylamino, hetsrocyclylcarbonylamino, cycloalkylalkoxy,cycloalkenylalkoxy,cycloalkynylalkoxy, . arylalkoxy, hetarylalkoxy or heterocyclylalkoxy, and their plant-tolerated acid addition products and base addition products not only have high fungitoxic, insec-ticidal, nematocidal and acaricidal activity but al~o are vQry well tolerated by plants.
Acids for acid addition products are, for example, mineral acids, for example hydrochloric acid, hydrobromic acid, phosphoric acid, sulfuric acid or nitric acid, cr carbo~ylic acids, such as formic acid, acetic acid, oxalic acid, malonic acid, lactic acid, malic acid, succinic acid, tartaric acid, citric acid, salicylic acid, p-toluenesulfonic acid or dodecylbanzenesulfonic acid, and also protic compounds generally, eg. ~accharin.
Base~ for base addition products are, for 21005~6 - 10 - O.Z. 0050/43411 example, potassium hydroxide, sodium hydroxide, potassium carbonste, ~odium carbonate and ammonium hydroxide.
The novel compounds of the formula I may be obtained in the preparation as mixtures of ~tereoisomers (E/Z isomer6, diastereomer~, enantiomer~), which can be separated into the individual components in a convention-al manner, for example by crystallization or chromatog-raphy. Both the individual isomers and mixtures thereof can be used a~ fungicide~, acaricides, namatocides or insecticides and are embraced by the present invention.
~he stated alkyl radicals are preferably of 1-10 carbon atoms, are substituted or uneub~tituted and are, for ex~mple, methyl, ethyl, propyl, n-propyl, i~opropyl, butyl, n-butyl, isobutyl, tert-butyl, ~ec-butyl, pentyl, pent-l-yl, pent-2-yl, pent-3-yl, 2-mathylbut-1-yl, 2-methylbut-2-yl, 2~methylbut-3-yl, 3-methylbut-1-yl, 2,2-dLmethylprop-l-yl, hexyl, hex-l-yl, hex-2-yl, hex-3-yl, l-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methyl-pentyl, 1,l-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, l-ethylbutyl, 2-ethylbutyl, 1,1,2-tri-methylpropyl, 1,2,2-trimethylpropyl, l-ethyl-l-methyl-propyl, l-ethyl-2-methylpropyl, heptyl, hept-l-yl, hept-2-yl, hept-3-yl, hept-4-yl, l-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, l-ethyl-pentyl, 2-ethylpentyl, 3-ethylpentyl, l-propylbutyl, 1-isopropylbutyl, octyl, oct-l-yl, oct-2-yl, oct-3-yl, oct-4-yl, l-methylheptyl, 2-methylheptyl, 3-methylheptyl, 4-methylheptyl, 5-methylheptyl, 6-methylheptyl, l-ethyl-hexyl, 2-ethylhexyl, 3-ethylhexyl, 4-ethylhexyl, 1-propylpentyl, 2-prcpylpentyl, nonyl, non-1-yl, non-2-yl, non-3-yl, non-4-yl, non-5-yl, l-methyloctyl, 2-methyl-octyl, 3-methyloctyl, 4-methyloctyl, 5-methyloctyl, 6-methyloctyl, 7-methyloctyl, 4-Me~hyl-2-propylpentyl, decyl, dec-l-yl, dec-2-yl, dec-3-yl, dec-4-yl, dec-5-yl, 1-ethyloctyl, 2-ethyloctyl, 3-ethyloctyl, 4-ethyloctyl, 5-ethyloctyl, 6-ethyloctyl or 2-propylheptyl.

21~0~4~

~ O.Z. 0050/43411 The stated alkenyl radicals are preferably of 2-10 carbon atoms, are unsubstituted or sub~tituted and are, for example, ethenyl, propenyl, l-propenyl, 2-propenyl, butenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, pentenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, l-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl,2-methyl-3~butenyl,3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-2-propenyl, hexenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, S-hexenyl, l-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, l-methyl-3-pent~nyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, l,l-dimethyl-3-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dImethyl-3-butenyl, 1,3-dimethyl-2-but~nyl, 1,3-dLmethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-2-butenyl, l-ethyl-3-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, l-ethyl-l-methyl-2-propenyl, heptenyl, octenyl, nonenyl or decenyl.
The stated alkynyl radical~ are preferabyl of 2-10 car~on atoms, are ~ubstituted or unsubstituted and are, for example, ethynyl, propynyl, l-propynyl, 2-propynyl, butynyl, l-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, pentynyl, l-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1,1-dimethyl-2-methyl-2-pentynyl, hexynyl, l-methyl-3-pentynyl, 1-methyl-4-pentynyl, 1-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dLmethyl-3-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl, heptynyl, octynyl, nonynyl, or decynyl.

21~03~
- 12 - O.Z. 0050/43411 The stated halogens are fluorine, chlorine, bromine or iodine.
The stated cycloalkyl radicals are preferably of 3-10 carbon atoms, are substituted or unsubstituted and are, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclo-decyl, bornanyl, norbonanyl, dicyclohexyl, bicyclo-[3.3.0]octyl~ bicyclo[3.2.1]octyl, bicyclo[2.2.2]octyl or bicyclo[3.3.1]nonyl.
The stated cycloalkenyl radical6 are preferably of 3-10 carbon atoms, are unæubstituted or substituted and are, for example, cyclopropenyl, ~yclobutenyl, cyclopentenyl, ~yclohexenyl, cycloheptenyl, cyclooctenyl, cyclononenyl, cyclodecenyl, bornenyl, norbonenyl, lS bicyclo~3.3.0]octenyl, bicyclo[3.2.1]octenyl, bicyclo[2.2.2]octenyl or bicyclo[3.3.1]nonenyl.
The ctated cycloalkynyl radicals are preferably of 6-10 carbon stom6, are unsubstituted or substi~uted and ara, for example, cyclohexyne, cycloh~ptyne, cyclo-octyne, cyclononyne, cyclodecyne, cycloundecyne or cyclo-dodecyne.
The stated haloalkyl radical~ are preferably of 1-4 carbon atoms, are unsub~tituted or substituted and are, for example, chloromethyl, dichloromethyl, tri-chloromethyl, fluoromethyl, difluoromethyl, trifluoro-methyl, chlorofluoro~ethyl, dichlorofluoromethyl, chloro-difluoromethyl, l-fluoroethyl, 2-fluoroethyl, 2,2-di-fluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoro-ethyl,2-chloro-2,2-difluoroethyl,2,2-dichloro-2-fluoro-ethyl, 2,2,2-trichloroethyl or pentafluoroethyl.
The stated aryl radicals are preferably of 6, 10 or 14 carbon atoms, are un6ubstitut~d or substituted and are, for example, phenyl, naphthyl, l-naphthyl, 2-naphthyl, anthracenyl, 1-anthracenyl, 2-anthracenyl or 9-anthracenyl.
The tated hetaryl radicals preferably have 5-14 ring atoms, including 1-4 hetero atom~ ~elected from the 2100~46 - 13 - O.Z. 0050/43411 group consisting of N, 0 and S, are un~ubstituted or substituted and are, for example, furyl, 2-furyl, 3-furyl, thienyl, 2-~hienyl, 3-thienyl, pyrrolyl, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, isoxazolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, isothiazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, pyrazolyl, l-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, oxazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, thiazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, Lmidazolyl, 1-imidazolyl, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiazolyl, 1,3,4-thiadiazolyl, tetrazolyl, 1,2,3,4-thiatriazolyl, 1,2,3,4-oxatriszolyl, pyridyl, ~-pyridyl, ~-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.
Ad~acent 6ubs~ituents of the heteroaromatics may be condensed to form an aromatic or heteroaromatic ring, 80 that hetaryl al60 includes fus2d ring systems, eg.
benzofuranyl, isob~nzofuranyl, l-benzothienyl, 2-benzo-thienyl, indolyl, isoindolyl, benzisoxazolyl, benzoxazol, . benzi~othiazolyl, benzothiazolyl, 2-benzothiazolyl, 4-benzothiazolyl, 5-benznthiazolyl, 6-benzothiazolyl, 7-benzothiazolyl, indazolyl, benzimidazolyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, acridinyl, phenanthridinyl, carbazolyl, quinolyl, i6iquinolyl, phthalazinyl, quinazolinyl, quinoxalinyl, cinnolinyl, 1,5-naphthyridinyl,1,6-naphthyridinyl,1,7-naph~hyridin-yl, 1,8-naphthyridinyl, pteridinyl, pyrrolopyridinyl, pyrrolopyridazinyl,pyrrolopyrLmidinyl,pyrrolopyrazinyl, pyrrolotriazinyl, furopyridinyl, furopyridazinyl, furo-pyrimidinyl, furopyrazinyl, furotriazinyl, thienopyridin-yl, thienopyridazinyl, thienopyrimidinyl, thienopyrazin-yl, thienotriazinyl, Lmidazopyridinyl, ~midazopyridazin-yl, imidazopyrimidinyl, imidazopyrazinyl, pyrazolo-pyridinyl, pyrazolopyridazinyl, pyr~zolopyrimidinyl, 210054~
- 14 - O.Z. OOS0/43411 pyrazolopyr~zinyl, isoxazolopyridinyl, isoxazolo-pyridazinyl, isoxazolopyrimidinyl, i~oxazolopyrazinyl, oxazolopyridinyl,oxazolopyridazinyl,oxazolopyrimidinyl, oxazolopyrazinyl,thi~zolopyridinyl,thiazolopyridazinyl, S thiazolopyrimidinyl, thiazolopyrazinyl, isothiazolo-pyridinyl, isothiazolopyridazinyl, isothiazolopyrimidin-yl, isothiazolopyrazinyl, triazolopyridinyl, triazolo-pyridazinyl, triazolopyrimidinyl or triazolopyrazinyl.
'~he stated heterocyclyl radicals preferably have 3-15 ring atoms, including 1-4 hetero atom~ 3elected from the group con~isting of N, 0 and S, are saturated or have parallel un~aturated bonds, are unsub~tituted or substituted and are, for example, 2-tetrahydrofuranyl, oxiranyl, 3-tetrahydrofuranyl, 2-totrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 4-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, S-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-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl,1,2,4-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, ~,5-dihydrofur-2-yl, 2,5-dihydrofur-3-yl, 2,3-dihydrofur-3-yl,2,3-dihydrothien-2-yl,2,3-dihydrothien-3-yl, 2,5-dihydrothien-2-yl, 2,5-dihydrothien-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-i30x~zolin-2-yl,2,3-i~oxazolin-4-yl,3,4-i~oxazolin-4-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-isothi~zolin-4 yl, 2,3-i~othiazolin-5-yl, 3,4-i~othiazolin-5-yl, 4,5-isothiazolin-5-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, 3,4-210~
- 15 - O.Z. 0050/43411 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,2,3-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-yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydro-oxazol-4-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 3-tetrahydropyridazinyl, 4 tetrahydropyridazinyl, 2-tetrahydropyr- idinyl, 4-tetrahydropyrimidinyl, 5-tetra-hydropyrimidinyl, 2-tetrahydropyrazinyl, 1,3,5-tetra-hydrotriazin-2-yl, 1,2,4-tetrahydrotriazin-3-yl, 1,3-dihydrooxazin-~-yl, 1,3-dithian-2-yl, oxazol-2-yn-2-yl, 3,4,5,6-tetrahydropyridin-2-yl, 4H-1,3-thiazin-2-yl, 4H-3,1-benzothiazin-2-yl, 1,1-dioxo-2,3,4,5-tetrahydrothin-2-yl, 2H-1,4-benzothiazin-3-yl, 2H-1,4-benzoxazin-3-yl, 1,3-dihydrooxazin-2-yl, 1,3-di~hian-2-yl, N-morpholinyl or dihydroquinazolinyl.
Expressly included are those heterocyclic radi-cals which carry further functional groups, for ex2mple oxo or thioxo groups, 80 that the heterocyclyl radicals -- also include cyclic e~ters, thioester~ or amides or thio analogs thereof, for example pyrrolidonyl, piperidonyl, 1-azacycloheptan-2-onyl, imidazolidinonyl, diketo-piperazinyl or thiopyrrolidonyl.
The novel compound~ can be prepared, for example, by the following processes:
For e~cample, the phenol 1 ~EP 251 082) can be reacted with the corre~ponding alkylating agents under alkaline condition~ (for exampla, alkali metal carbonates in dipolar sprotic ~olvents, ~uch a4 dimethylformamide, N-methylpyrrolidone, tetrnmethylurea, dimethylpropylene-ure~, dimethylsulfoxide, sulfolane, etc.) to give the novel compound6 2 (Schame 1) 2100~6 - 16 - O.Z. 0050/43411 Scheme 1 X Y

B O ~
X Y R'02C ORZ

1 ~ 1 2 HO ~ ~ X Y X Y

RlO C ~ oR2 OR~

la lb The hetarylation of the phenol 1 i~ known (EP 242 081) bu the alkylation of 1, in particular with unreac-tive alkylating agent~, to give the ethsrs 2 pre~ents problems since the cyclization of 1 to la or lb is the only detectable reaction in ~ome cases (Scheme 1). This formation of byproducts can be suppre~ed if relatively highly concentrated solution6 are smployed to incr2a~e the reaction rate of the bimolecular reaction between the phenol 1 ~nd ~lkylating agent Hal-B (Hal = Cl, Br or I) ~o give the active ingrEdisnts 2, and the reaction is carried ou$ in the pre~ence of catalytic amounts of iodine ~alts (eg. ~aI or RI) in, for example, ~he above-mentisned dipolar aprotic solvents in order to activate unreactive alkylating agent~ (~al = Cl or Br).
The active ingredients 2 ~re obtained in a similar manner by reacting the phenol 1 with alcohols under the condition~ of the Nitgunobu reaction (Synthesis 1981, 1).
Furthermore, the phenylacetates ~ can be reacted 2100~6 - 17 - O.Z. 0050/43411 under alkaline conditions to give the formylated products 4, which can be alkylated to the novel compounds 3 (Scheme 2).
Scheme 2 X Y X Y X Y

B`o~ _ B`o~f -- B~o~
Rl02 R'O2 OH Rlo2 OR2 Moreover, the ketoesters 5 c~n be ~ub~ected to a Wittig reaction with (C6H5)3Pt-CH2-O-R2-Cl to give the novel compound~ 2 (Sche~e 3).
Scheme 3 X Y X Y

B~ ~ ~ B~ ~

RIOz O R102 OR2 The chemical litarature describes many methods for the synthesis of the ~-ke~oesters 5 (cf. ~or example L. Weinstock et al., Synthe~ic Communications 11 (1981), 943-946; J. March, Advanced Organic Chamistry, 3rd Edition (1985), J. Wiley & Son~; R. Larock, Comprehen6ive Qrganic ~ransformations, 1st Edition 1989, VCH Publi6h-ers; N. ~ie~er, Reagents for Organic Synthesi~, J. Wiley & Sons); the synthesi~ of the kstoesters 5 6tar~ing from benzaldehyde 6 via a cyanohydrin route (EP 422 597), starting from ortho-haloaromatics 7 (~al = Cl, Br or I) via a Grignard route (EP 253 213~ 8tarting ~rom benzoates 2100~4~

- 18 - O.Z. 0050/43411 via a P~mmerer rearrangement (J. Amer. Chem. Soc. 1966, 5498; Synthe~is 1982, 41) starting from acetophenones 9 via an oxidation/esterification (Synthetic Communications 21 (1991), 2045; J. Prakt. Chem. 45 (1892), 377) or starting from benzoyl cyanides 10 (Tetrahedron ~ett.
1980, 3539; Scheme 4) i8 mentioned here merely by way of example.

Scheme 4 X y X Y X

o~ ~ ~0~ ~0 CHO Hal R'02C

B~ ~

RIO~C o X Y X Y

B~ ,1~1 B~ ,1~

H3C O 2 NC O lQ

Furthermore, the novel compounds 2 are obtainable from the phenylacetates 3 via enhmine formation to give 2100~46 - l9 - O.Z. 0050/43411 lI, hydroly6is of the enamine to give the formyl deriva-tive 4 (cf. Scheme 2) and alkylation of the formyl derivative (6imilarly to DE 40 25 892) (Scheme 5).
Scheme 5 ~ `0 ~ B~ ~
R'02C R~02C N(AU~1)2 Rl02C OH

X Y

B~oJ~

RIO2C OR~

Moreover, the enol ethers 2 can be prep~red by eliminating an alcohol RZ-O~ from the acetals 12 (J. Chem.
Soc. Chem. Co~mun. 1980, 838; Chem. Lett. (1976), 796) and can be obtained from the acrylate~ 13 by 6ucce~6ive reaction with bromine, an alcoholate R2-O-M (M = Li, Na, 10 ~, Mg) and a protic acid, eg. NaHSO~ (~. Chem. Soc. 1958, 153) (~imilarly to EP 431 323; Scheme 6).

210054~
\

- 20 - O.Z. 0050/43411 Scheme 6 X Y X Y X Y

~ OR: ~0 ~ B
R'02C oR2 R~02C OR2 ~ Rl02C
12 2 l3 Moreover, the propargyl ether 14 i8 a u~eful intermediate for the synthe~i~ of the novel compounds 15 and 16. For example, the reaction of 14 with aldehyde oximes Rl-CH~NOH in the presence of NaOCl solution gives the isoxazole 15, and the reaction of 14 with aryl or hetaryl halides (HA1 = I or Br) in the presence of a Pd catalyst gives the acetylene 16 (Scheme 7).
Sch~me 7 N' oJ~ oJ~ ~~
R10 2 OR R10 oR2 R~02C OR~

The Ex2mples which follow illustrate the prepara-tion of the novel compounds.
E~ANPLE 1 ~ethyl ~-(2-(b~nzoylmethoxy)-phenyl)-B-methoxya~rylate (Table 3, No. 18) A mixture of 2.1 g (10 mmol) of methyl ~-(2-hydroxyphenyl)-~-methoxyacryl~te (EP 251 082), 2.0 g (10 mmol) of phenacyl bromide and 1.5 g (11 mmol) of R2CO3 in 5 ml of di~ethylformamide is ~tirred overnight at room t~mperature. An additional O.6 g of phenacyl bromide and 0.5 g of R2C03 are then added.

2100~46 - 21 - O.Z. 0050/43411 Stirring is carried out for 6 hours at room temperature (20~C), the reaction mixture i~ dilu~ed with wster and the aqueous phase i8 extracted three times with methyl tert-butyl ether. The organic phase i6 dried over MgSO4 and evaporated down. The residue i8 purified by column chromatography u~ing hexane/ethyl acetate mixtures. 1.7 g (52~) of the title compound are obtained as a colorle~s solid (mp. = 76C).
lH-NNR (CDCl3; ~ in ppm~:
7.95 (d, broad, 2 H, aromatic); 7.5 (m, 4 H, 3 x aroma-tic, 1 x vinyl); 7.25 (m~ 2 H, aromatic); 7.0 (t, 1 H, J = 8 Hz, aromatic); 6.9 (d, 1 H, J - 8 Hz, ~romatic);
5.2 (B, 2 H, O-CH2); 3.8 (~, 3 H, O-CH3); 3.65 (8, 3 H, O-CH3) EXA~PLE 2 Methyl ~-(2-((N-phenylpyrrolidon-3-yl)-oxy)-phenyl)-~-methoxyacrylate (Table 3, No. 16) a) 2-((N-Phenylpyrrolidon-3-yl)-oxy)-benzaldehyde 3.2 g (0.13 mol) of sodium hydride are added to 14.8 g (0.12 mol) of salicylaldehyde in 100 ml of di-methylformamide wi~h gentle cooling. After evolution of gas has ceased, 29 g (0.12 mol3 of 3-bromo-N-phenyl-- pyrrolidone (pr~pared similarly to J. ~ed. Chem. 30 (1987), 1995) are added and stirr$ng i8 carried out overnight at room temperature. Thereafter, the reaction mixture i8 diluted wi~h water and the aqueous phase is extracted thrQe times with methyl tert-butyl ether. The combined organic phases are dri~d over MgSO4 and evapora-ted down. The residue i~ purified by column chromatog-raphy. 12.8 g (39%) of the title compound are obtained as a pale yellow solid.
H-NMR (CDC13; ~ in ppm):
10.5 (8, 1 H, CHO); 7.0-8.0 (m, 9 H, aromatic); 5.15 (t, 1 H, J = 8 Hz, O-CH); 3.9 (m, 2 H, N-CH2); 2.7 (m, 1 H, C~H~); 2.4 (m, 1 H, CH~) b) Methyl 2-((N-Phenylpyrrolidon-3-yl)-oxy)-phenyl-glyoxylate 2100~46 - 22 - 0.~. OOS0/43411 A mixture of 12.8 g (45 mmol) of the aldehyde from Example 2a in 100 ml of methylene chloride and S g (100 mmol) of sodium cyanide and 5 g (94 mmol) of am-monium chloride in 100 ml of water i~ stirred for 3 hours at room temperature. Thereafter, the organic phase is separated off and the aqueous phase is extracted twice with methylene chloride. The combined organic phases are dried over ~gS04 find evaporated down. The residue is taken up in 100 ml of methanol, and 20 ml of 3 N hydrochloric acid in ether are added. Stirring i8 carried out overnight at room temperature and the reaction mixture is then evaporated down undar reduced pressure.
Ths residue i8 taken up in 100 ml of water and heated at lOO-C for 30 minutes, a viscou~ oil ~eparating out. The water i~ decanted and the residue is taken up in methylene chloride. The organic phase is dried over MgSO4 and evaporated down.
The residue i8 taken up in 100 ml of methylene chloride, and a solution of 0.3 g of RBr, 0.7 g of NaH2PO4-H20 and 0.9 g of Na2HPO~ 2H20 in 100 ml of water iB
added. 0.2 g of tetramethylpiperidine N-oxide is then added, followed by 40 ml of chlorine bleach (co~tains -- 12.5% of active C12) while stirrin~ vigorously. Stirrin~
i8 continu~d for 1 hour at room temperature, the aqueous phase i~ ~eparated off, a further 40 ml of chlorine bleach are added and stirring is continued for a further hour. The organic phase i8 then separated off, extracted onco with w~ter, dried over MgSO4 and evaporated down. The residue iB purified by column chromatography. 6.4 g (42~) of the title compound are obtained as a beige solid ~mp. - llQC).
H-NNR (CDCl~; ~ in pp~):
7.9 (d, broad, 1 H, hromatic); 7.7 (d, 2 H, J = 8 Hz, aromatic); 7.6 (t, broad, 1 H, aromatic); 7.4 (t, 2 H, J = 8 Hz, aromatic); 7.3 (d, 1 H, J = 8 Hz, aromatic); 7-7.25 (m, 2 H, aromatic); 5.15 (t, 1 ~, J = 8 Hz, 0-CH);
4.0 (m, 1 H, N-C~hHB); 3.85 (m, 1 H, N-CH~; 3.85 (s, 3 2100~6 - 23 - O.Z. 0050/43411 H, -0-CH3); 2.65 (m, 1 H, -C~hH~); 2.3 (m, 1 H, -CH~) c) Methyl ~-(2-((N-phenylpyrrolidon-3-yl)-oxy)-phenyl)-B-methoxyacrylate (Table 3, No. 16) 4.0 g (11 mmol) of methoxymethyltriphenyl-S phosphonium chloride in 1 g (9 ~mol) of pota~ium tert-butylate in 50 ml of tetrahydrofuran are stirred for 30 minutes at room temperature. The mixture i~ then cooled to -20C, 2 g (5.9 mmol) of the ketoester from Example 2b are added and the mixture i~ 810wly allowed to warm up to room temperature. Stirring is continued for 2 hours at room temperature, ths re~ction mixture i8 diluted with water and the aqueou~ phase is extracted three time~ with methyl tert-butyl ether. The combined organic phases are drisd over ~gS04 and evaporated down. The residue is purified by column chromatography using hexane/ethyl acetate mixtures. 1.4 g (65%) of the trans-icomer of the title compound are obtained as a pale yellow oil.
H-NNR (CDCl3; ~ in ppm):
7.7 (d, broad, 1 H, aromatic~; 7.5 (~, 1 H, vinyl); 6.9 -7.45 ~m, 8 H, aromatic); 4.95 (t, 1 H, J = 8 Hz, 0-CH);
3.7 - 4.0 (m, 2 H, N-CH2); 3.8 (8, 3 H, 0-CH3); 3.7 (s, 3 H, 0-CH3); 2.45 (m, 1 H, -C~bH~); 2.25 (m, 1 H, -CH~) Methyl c-(2-(3-(meta-methylphenyl)-prop-2-ynyloxy)-phenyl)-A-methoxyacrylate (Table 3, No. 6) a) Methyl 2~(prop-2-ynyloxy)-phenylacetate 13 g (O.54 mol) of sodium hydride are added a little at a time to 75 g (O.45 mol) of methyl ortho-hydroxyphenylacetate in 500 ml of dimethylformamide.
Gentle cooling i8 carried out. After 30 minutes at room temperature, the evolution of gas has ceased, and 65 g (0.54 mol) of propargyl bromide are added. S~irring is carried out overnight at room tamperature, a~ter which the reaction mixture i8 diluted with 1 1 of water and the aqUeOU8 pha8e i8 extracted three times with ~ethyl tert-butyl ether. ~he combined organic pha~es are dried over MgSO4 and evaporated down. The regidue i8 di~tilled.

2l0n~46 - 24 - O.Z. 0050/43411 7I.6 g (78%) of the title compound are obtained as a pale yellow liquid (bp. (0.3 mbar) = 98-100C).
H-NNR (CDCl3; 6 in ppm):
7.25 (m, 2 H, aromatic); 7.0 (m, 2 H, aromatic); 4.7 (d, 1 H, J = about l Hz, O-CH2); 3.7 (s, l H, O-CH3), 3.65 (s, 2 H, CH2); 2.5 (t, 1 H, J = about 1 Hz, =CH~
b) hethyl ~-(2-propynyloxyphenyl)-B-methoxyacrylate A mixture of 20 g (0.1 mol) of the phenylacetate from Example 3a, 20 ml of methyl formate and 2.7 g (0.11 mol) of sodium hydride in 100 ml of tetrahydrofuran is stirred at room temperature. Gas evolution which is initially 810w and then vigorous occurs. Once the evolution of gas ha~ cea~ed, the r~action mixture is diluted with water and the ~queous ph~se is sxtracted twice with methyl ~ert-butyl ~ther. Thase organic phaseæ
are diEcarded. The aqu~ou~ pha~e i~ then acidified and i~ extracted three times with me~hyl tert-butyl ether.
The combined ph~ses are ~iltered under suction with a ~ilica gel and evaporated down.
The re~idue i8 taken up in 200 ml of acetone, 2nd 14 g ( n . 1 mol) of R2C03 ~nd 11 g (0.09 mol3 of dimethyl sulfate are added. Stirring i~ carried out for 4 hours at room temperature, sfter which the reaction mixture is evzporated down. The residue i8 taken up in methylene chloride. The organic pha~e is wa~hed with dilute ammonia and water, dried over MgSO~ and evaporated down. The residue i8 purified by column chromatography using hexane/ethyl acetate mixtures. 11 g (45%) of the trans-isomer of the title compound are obtainzd a8 a pale yellow solid.
H-NMR ~CDCl3; ~ in ppm):
7.5 (6, 1 H, vinyl), 7.25 (m, 2 H, aromatic); 7.05 (m, 2 H, aromatic); 4.65 (d, 2 H, J = about 1 Hz, O-CH2); 3.8 (8, 3 H, 0CH3); 3.7 ( , 3 H, O-CH3); 2.5 (t, 1 H, J =
about 1 Hz, =CH) c) Methyl ~-(2-(3-(meta-methylphenyl)-prop-2-ynylOXy)-phenyl-~-methoxy~crylate (Table 3, No. 6) 210~5~6 - 25 - O.Z. 0050/43411 A mixture of 2 g (8.1 mmol) of the propargyl ether from Example 3 b, 1.8 g (8.2 mmol) of meta-iodo-toluene, 2 g (20 mmol) of triethylamine, 0.3 g of tri-phenylphosphine, 20 mg of CuI and 60 mg of palladiumlII) acetate in 20 ml of dimethylformamide is stirred for one hour at 70C. Thereafter, the reaction mixture i8 diluted with water and the agueous phase i8 extracted three tLmes with methyl tert-butyl ether. The combined organic phases are dried over MgS0~ and evaporated down. The residue is purified by column chromatography using hexane/ethyl acetate mixture~. 0.9 q (33%) of the title compound is obtained aR a crystalline solid (mp. = 76C).
H-NMR (CDCl3; ~ in ppm):
7.5 (~, 1 H, vinyl); 6.9-7.4 (m, 8 H, aromatic); 4.9 (s, 2 H~ 0-CH2); 3-8 (8, 3 H, 0-CH3); 3.7 (8, 3 H, 0-CH3); 2.5 (8, 3 H, CH3) Methyl ~-(2-((3-para-methylphenyliosxazol-5-yl)-methoxy)-phenyl)-~-methoxyacrylate (Table 3, No. 13) 50 ml of chlorine bleach (contains 12.5% of active C12) i8 added to a ~olution of 2 g (8.1 ol) of the propar~yl ether from Example 3 b and 1.7 g (12.5 - mmol) of p-methylbenzaldehyde oxime in 30 ml of methylene chloride. Stirring is csrried out for 30 minute~ at room temperhture, the phase~ are separated and the agueous phase i8 extracted three times with methylene chloride.
The combin~d organic phases ~re extracted once with water, dried over MgS0~ ~nd ~vaporsted down. The residue crystallize~ and is stirred thoroughly with methyl tert-butyl ether/hexane. 1.9 g (62%) of the trans-isomers of the title compound aro obtained as a pale yellow solid ~mp. = 82C).
H-NMR (CDCl3; ~ in ppm):
7.7 (d, 2 H, J = 8 Hz, aromatic); 7.55 (8, 1 H, vinyl);
7.25 (m, 4 H, aromatic); 7.0S (m, 2 H, aromatic); 6.6 (s, 1 H, i~oxazol); 5.2 (8, 2 H, 0-CH2); 3.85 (8 3 H, 0-CH3);
3.7 (8, 3 H, 0-CH3); 2.4 (8~ 3 H, CH3) -`` 2100~46 - 26 - O.Z. 0050/43411 The compounds stated in the Tables below can be prepared in a similar manner.

BASF A~t~en~e~ell~cb~t 920400 O.Z. 0050/43411 27 2100~

Table 1 ~0~

H3CO2C ~ CH3 ~n Table 1, B may have the following meanings:

1: -C~H2-C(=O ~ m X

II: -CH2-C(=N OCH ~ m -CH2-C(-N-O-CH2-C ~ m Xm IV: -CH2-CH(-OCH ~ X

~ m V: -CH2-CH(-O-CH2-CI~

VI: -CH2-C(CO)- N:~ m BASF Aktien5~e~ell~lchaÇt 920400 O.Z. 0050/43411 2100~6 Vll: -CH2-C(=O)-N(CH,~ m Xm VIII: --C~z-c(=o)-N(--CH3)-CU~X

~X: -CH2-C(=O)-N(-CH2-CI~ m X: ~N~X~

Xm XI: ~N~

Xm XII~ ~N~

XIII: ~N~i ~ASF Aktie~e~ell~chaft 920400 O.Z. 0050/43411 21~0~6 O

xv ~N

XVI: ~ ~m XV I I: ~ CH~xm .--XVII~: ~ ~ m X

~ m XIX ~CH~

BASF Akt~en~ ellschaft 920400 O . Z . 0050/43411 2100~

/ m xx~
X

m ~C~

XXI: l l ~ X
XXII: ~ m . ~Xm XXIII: ~CH~"N~J~
o BASF A~ti-nge~ell~ch~t 920400 O.Z. 0050/43411 31 ~lOQ~

In Table 1 the compounds given below have for example the following meanings:

H3CO2C~ ~CH

~ ,CH~
II/l.ll:I .
H3C02~ ~ CH3 VII/1.66: ~ ~CH~N~

. H3CO2C~ ~CH3 ~

X/l 160:~ ~N~OCH3 H3CO2C `CH3 H3C02C~ ~

BASF A~tie~e~ellschaft 920400 O.Z. 0050/43411 32 2 1 ~ a ~ 4 ~

For each of the groups B (I to XXIII) Xm may have the fol-lowing meaning Table 1 ~ ~ B

H3CO2C ~ CH3 No. Xm 1 4-C(=O)-C6H5 . . ..

,, _ _ , .
~ ~ ~
6 2,4,6-F3 2,3,4,5,6-F5 8 2,3-F2 _ 9 , ~
3-Cl . _ . . -. ~ __ _ _ _ _ _ 13 2,4-C12 . . . .. _ . . . .. __ . 14 2,5-C12 . _ - .. __ .. .....
15 __ _ 16 3,4-C12 .
17 3,5-C12 18 2,3,4-C13 19 '-----2,3,6-C13 21 ~ -22 2,4,6-Ci~
23 3,4,5-Cl3 ~ .. _ BASF A~ti~nge~ellrch~ft 920400 O.Z. 0050/43411 33 2 1 0 0 ~ 4 5 No. Xm 24 2,3,4,6-Cl~
2,3,5,6-Cl4 26 2,3,4,5,6-Cl5 27 2-Br 28 3-Br ..
29 4-Br 2~4-Br2 2~5-Br2 32 2~6-Br2 33 2,4,6-Br3 . . .
34 2,3,4,5,6-Br5 __ _ 38 2,4-I2 . ,_ 2-Cl, 3-F
2-Cl, 4-F
_ , , . ,_ 412-Cl, 5-F
422-Cl, 6-F
. _ 43 2-Cl, 3-Br . ~
44 2-Cl, 4-Br _ _ . .. , ..... __ 2-Cl, 5-Br 46 . ~
47 .. 2-Br, 3-Cl 48 2-Br, 4-Cl .... _ _ _ 49 2-Br, 5-Cl _ ,,_ , _ 2-Br, 3-F
_ , , _ . _ -51 2-Br, 4-F
52 2-Br, 5-F
_ 53 2-Br, 6-F
54 2-F, 3-Cl . . , , - ._ . 2-F, 4-Cl 56 2-F, 5-Cl 57 3-Cl, 4-F
58 3-Cl, 5-F
59 3-Cl, 4-Br _ . ,.

BASF Aktien~sellschaft 920400 O.Z. 0050/43411 .
No. Xnl 3-C1, 5-Br . ~ ...... ... .~ . .
61 3-F, 4-Cl 62 3-F, 4-Br 63 3-Br, 4-Cl 64 3-Br, 4-F
., 2,6-C12, 4-Br . .

68 4-CHl 69 2,3-(CH3)2 2,4-(CH3)2 . . , ~ _ 71 2,5-(CH3)2 72 2,6-(CH3)2 73 3,4-(CH3)2 74 3,5-(CH3)2 2,3,5-(CH3)3 76 2 3 4-(CH3)3 _ 78 2,4,5-(CHl)3 79 2,4,6-(CH3)3 _ 3,4,5-(CHlil 81 2,3,4,6-lCH3)~
82 2,3,5,6-(CH~)4 83 . 2,3,4,5,6-(CH3) r, 84 2-C~Hs 3-C~H' 86 4-C2Hs 87 2,4-(C2Hs)2 88 2,6-(C2Hs)2 89 3,5-(C2Hs)2 _ _ 2,4,6-(C2H5)3 91 2-n-ClH7 . ... _ .
92 3-n-C3H7 93 4-n-C3H7 _ .. . , _.~ , 94 2-i-C3H7 3-i-ClH7 BASF ~Uktien~e~ell~c~u~ft 920400 O.Z. 0050/43411 210~;-,4~

No ~ xm 96 4-i-C3H7 97 2,4-(i-C~H7)~
98 2,6-(i-CIH7) 99 3,5-(i-C3H7j 2 lO0 2,4,6-(i-C3H7)3 . -.. .
101 2-s-C4Hg . _ 102 3-s-C4Hg 103 4-s-C4Hg 104 2-t-C4Hg 105 3-t-C4Hg ;
106 4-t-C4Hg 107 2,3-(t-C4Hs) 2 108 2,4-(t-C4Hg)-,.
109 2,5-(t-C4Hg), llO 2,6-(t-C4Hg)~
lll 3,4-(t-C4Hg)~
112 2,4,6-(t-C4Hg)3 . .... ,_ _ _ 113 4-n-CgH1g 114 . 4-n-ClzH2s 115 4-n-C1sH31 . .
116 4-(1,1,3,3-tetramethylbutyl) 117 4-(2,4,4-trimethylpropyl) 118 2-t-C4Hg, 4-CH3 .
ll9 2-t-C4Hg, 5-CH~
120 . 2,6-(t-C4Hg)~, 4-CH3 121 2-CH3, 4-t-C4Hg 122 2-CHl, 6-t-C4Hg 123 2-CH-1, 4-i-ClH7 124 2-CH3, 5-i-C3H7 125 3-CH3, 4-i-C3H7 126 2-i-C3H7, 5-CH3 127 2,4-(t-C4Hg)~, 6-i-C~H7 128 2-allyl 129 3-allyl 130 4-allyl 131 2-allyl, 6-CH, BASF ~ tien~ooellsch~ft 920400 O.Z. 0050/43411 21~ ~ ~ 4 i~

No. X~
132 ~ ly~`
133 3-cyclo-C6H
134 4-cyclo-C6Hll 135 2,4-(cyclo-C6HIl)2, 6-CH3 136 2-CH" 4-cyclo-C6H
137 2-CH.-C6H5 138 3-CH2-C6Hs 140 2-CH2-C6H5, 4-CH3 141 2-CH3, 4-CH7-C6H5 142 2-C6Hs 143 3-C6Hs 144 4-C6Hs 145 4-(2-i-C3H7-C6Hg) 146 4-C6H5, 2,6-(CH3)2 . . ..
147 2-Cl, 4-C6H5 148 2-Br, 4-C6H5 _ 149 2-C,H5, 4-Cl 150 2-C6H5, 4-Br 151 2-CH2C6H5, 4-Cl 152 2-CH2C6H', 4-Br .. 153 2-Cl, 4-CH2C6H5 '5g 2-Br, 4-CH2C6Hr 155 2-cyclo-C6Hll, 4-Cl 156 2-cyclo-C6Hll, 4-Br 157 2-Cl, 4-cyclo-C6H
158 2-Br, 4-cyclo-C6H

162 2-OC~Hs 163 3-O-C2Hs 165 2-O-n-C-~H
166 3-O-n-C,H-I
167 4-O-n-C~H7 BASF Aktien~e~ell~chaft 920400 O.Z. 0050/43411 37 210~546 NO. X,l~
168 2-O-i-ClH7 169 3-o-i-C3H7 170 4-o-i-C3H7 171 2-o-n-C6Hl3 172 3-O-n-C6H13 173 4-O-n-C6H13 174 2-O-n-C8HI7 175 3-O-n-Ci3H17 176 4-O-n-C~3HI7 178 ~ 3-O-CH2C6H5 180 2-O-(CH,)~C~,H5 181 3-O-(CH~)3C6H' 182 4-O-(CH~)3C6H5 183 2,4-(OCH3)2 187 2-OCFl 190 3-OCH2CHF~

. 2-CH" 3-Cl 198 2-CH3, 4-Cl . ...
199 2-CH~, 5-Cl . .
200 2-CH~, 6-Cl 201 2-CH" 3-F
202 2-CH3, 4-F
203 2-CHl, 5-F

- ~ASF Aktien~esell~chaft 920400 ~.Z. 0050~43411 38 210~5~6 No. Xm ., . ~
204 2-CH3, 6-F
205 2-CH3, 3-Br 206 2-CH3, 4-Br 207 2-CH3, 5-Br 208 2-CH3, 6-Br 209 2-Cl, 3-CHl .
210 2-Cl, 4-CH3 211 2-Cl, 5-CH3 . . .
212 2-F, 3-CH3 213 2-F, 4~CH3 214 2-F, 5-CH3 215 2-Br, 3-CH3 216 2-Br, 4-CH3 . . _.__ 217 2-Br, 5-CH3 218 3-CHl, 4-Cl 219 3-CH3, 5-Cl 220 3-CH3, 4-F
22i 3-CHl, 5-F
222 3-CHl, 4-Br .. .,.__ 223 3-CH3, 5-Br 224 3-F, 4-CH3 225 3-Cl, 4-CH3 226 3-Br, 4-CH3 . . . _ _ 227 2-Cl, 4,5-(CH3)2 228 2-Br, 4,5-(CH3)2 229 _ 2-Cl, 3~5-(cH3)2 230 2-Br, 3,5-(CH3)~

231 2,6-Cl" 4-CH3 32 2,6-F2, 4-CH3 233 2,6-Br2, 4-CH3 234 2,4-Br~, 6-CH
235 2,4-F2, 6-CH3 236 2,4-Br~, 6-CHl - _ . , , ,, _ . -.
237 2,6-(CHl) , 4-F
. _ 238 2,6-(CH3)-, 4-Cl .. ~
239 2,6-(CHI) , 4-Br BASF Aktien~e~ell~chaft 920400 O.Z. 0050/43411 39 ~ i 0 No. X" - _ 290 3,5-(CHI)), 4-F
241 3,5-(CH~)2, 4-Cl 242 3,5-(CH3)~, 4-Br 243 2,3,6-(CH3)3, 4-F
244 2,3,6-(CH~)3, 4-Cl 245 2,3,6-(CH3)3, 4-Br 246 2,4-(CH~ , 6-F
247 2,4-(CH~) , 6-Cl 248 2,4-(CH3)`, 6-Br 249 2-i-C3H7, 4-Cl, 5-CH3 250 2-Cl, 4-NO2 _ -251 2-NO2, 4-Cl 252 2-OCH3, 5-NO2 253 2,4-Cl~, 5-NO2 254 . 2,4-C12, 6-NO2 255 2,6-Cl~, 4-NO~
256 2,6-Br2, 4-NO
257 2,6-J2, 4-NO~
258 . 2-CH3, 5-i-C3H7, 4-Cl _ 260 3-CO;CHl 262 2-CO~(C2Hs) 263 3-CO~(C2H~) 264 4-CO~(C~H~,) . . .. _ ____ 265 2-CO,(n-C~H7) 266 3-CO2(n-C3H7) .
267 4-CO (n-C~H7) 268 2-CO,(i-C3H1) . ~
269 __ 3-CO~(i-C3H7) 270 4-CO (i-C~H7) 271 2-CO2(n-C6H13) 272 3-CO,(n-C6HI~) 273 4-CO~(n-C~H~,) 274 2-CHi-OCH~
275 3-CH~-OCH~

BASF Akt~en~e~ell~chaft 920400 O.Z. 0050/43411 2 1 0 ~ c) No. X", 277 2-CH2O(C2H5) _ ~ . .
278 3-CH2O(C2Hs) .
279 4-CH2O(C2Hs) 280 2-CH2O(n-C3H7) 281 3-CH2O(n-C3H7) 282 . _ 4-CH2O(n-C3H7) 283 2-CH'O(i-C3H7) 284 ~
285 4-CH2O(i-C3H7) . __ 291 4-CO-CHl 292 2-CO-CH~-CH3 . _ 294 4-CO-CH2-CH~
295 2-CO-CH2-CH~-CH3 296 3-CO-CH2-CH2-CHl . .. .._ . , 298 2-CO-CH(CH3)-CH3 -- _ ~..... _ . . . ... _ . ._ 299 - 3-CO-CH(CH3)-CH3 . . _ . -- - . .
300 4-CO-CH(CH3)-CH3 . __ 301 2-Me-4-CHO
_, _ ,, 302 2-Me-4-CH3-CO
303 2-Me-4-CH3-CH2-CO
304 2-Me-4-CH3-CH4-CH~-CO
_ 305 2-Me-4-CH3-CH(CH3)-CO
306 2,S-Me2-4-CHO
307 2,5-Me2-4-CH3-CO
308 2,5-Me~-4-CH3-CH~-CO
309 2,5-Me2-4-CHl-CH -CH2-CO
310 2,5-Me2-4-CH.-CH~CH3)-CO
311~ 2-Cl-4-CHO

BASF AXt~en~esell~chaft 920400 O.Z. 0050/43411 41 210~

~ .....
No. xnl 312 2-Cl-4-CH3-CO
313 2-Cl-4-CH3-CH2-CO
314 2-Cl-4-CH3-CH(CH3)-CO
315 2,5-C12-4-CHO
316 2,5-Cl.-4-CH3-CO
317 2,5-Cl2-4-CH3-CH -CO
318 2,5-Cl~-4-CH3-CH2-CH2-CO
319 . 2,5-Cl~-4-CH3--CH(CH3)-CO
320 2-C(=NOCH3)-CH-1 321 3-C(=NOCH3)-CH3 322 4-C(-NOCH3)-CH
323 - 2-C(=NOC-H5)-CH-1 324 3-C(=NOC2H5)-CH3 325 4-C(=NOC2H5)-CH3 326 2-C(-NO-n-C3H7)-CH3 327 3-C(=NO-n-C3H7)-CH3 328 4-C(=NO-n-C3H7)-CH3 329 2-C(=NO-i-C3H7)-CH3 330 3-C(-NO-i-C3H7)-CH3 331 4-C(=NO-i-C3H7)-CH3 332 2-C(=NO-allyl)-CH3 333 3-C(=NO-allyl)-CH3 334 4-C(=NO-allyl)-CH3 .
335 - 2-C(=NO-trans-chloroallyl)-CH3 336 3-C(=NO-trans-chloroallyl)-CH3 . _ _ 337 4-C(=NO-trans-chloroallyl)-CH3 338 2-C(=NO-propargyl)-CH3 339 3-C(=NO-propargyl)-CH3 . ... __ 340 4-C(=NO-propargyl)-CH3 341 2-C(=NO-n-C4H~)-CH3 . .. , .. _ . __ .
342 3-C(=NO-n-C4H~)-CHl 343 4-C(=NO-n-C4H~ CH3 344 2-C(=NO-CH~-C~H~)-CH3 _ 345 3-C(=NO-CH~-C6H~)-CH
.
346 4-C(=NO-CH2-C6H~)-CH3 347 2-CHl-4-CH=NOCH~
_ . _ . -. .

BASF Aktiengeaell~ch~ft 920400 O.Z. 0050/43411 q2 210~a4~

No. Xm 348 2-CH~-4-CH=NOC,Hr 349 2-CH3-4-CH=NO-n-ClH7 .
350 2-CH3-4-CH=NO-i-C3H7 351 2-CH3-4-CH=NO-allyl 352 2-CH3-4-CH=NO-(trans-chloroallyl) 353 2-CHl-4-CH=NO-propargyl 354 2-CH~-4-CH=NO-n-C4Hg .~ _ 2-CH~-4-CH=NO-CH2-C6Hr, 356 2-CH~-4-(CH~-C=NOCH~) 357 2-CH3-4-(CH3-C=NOC2H5) 358 . 2-CH3-4-(CH3-C=NO-n-C~H7) 359 2-CHl-4-(CH3-C=NO-i-C3H7) 360 2-CHl-4-(CH3-C=NO-allyl) 361 2-CHl-4-(CH3-C=NO-trans-chloroallylj 362 2-CH3-4-(CH3-C=NO-propargyl) 363 2-CH3-4-(CH3-C=NO-n-C4Hg) 364 2-CH3-4-(CH3-C=NO-CH2-C6H5) 365 _ 2-CH3-4-(C2H5-C=NO-CH3) 366 2-CH3-4-(C2Hs-C=NO-C2H5) .. __ _ .
367 . 2-CH3-4-(C2Hs-C=NO-n-C3H7) . . _ . .
368 2-CH3-4-(C2Hs-C=NO-i-C3H7 , ..
369 2-CHl-4-(C~H~,-C=NO-allyl) , .
370 . 2-CH3-4-(C2H5-C=NO-trans-chloroallyl) . _ _ 371 -- 2-CH3-4-(C2H5-C=NO-propargyl) _ _ _ 372 2-CH3-4-(C2H5-C=NO-n-CqHg) 373 2-CHl-4-(C~H~-C=NO-CH~-C~-.H~!) 374 2,5-(CH3)~-4-(CH3-C=NOCHl) 375 2,5-(CH3)2-4-(CH3-C=NOC2HI~) 376 2,5-(CH3).-4-(CH3-C=NO-n-C3H7) 377 2,5-(CH~)~-4-(CH3-C=NO-i-C3H7) 378 2,5-(CHi)~-4-(CH~-C=NO-allyl) 379 2,5-(CH3)2-4-(CH~-C=NO-transchloroallyl) 380 2,5-(CH-~)~-9-(CH3-C=NO-proparyl) 381 2,5-(CH,),~-4-(CH-~-C=NO-n-CqHg) 382 2,5-(CH~),-4-(CH:.-C=NO-CH:-C6Hs) .
383 2-C~,H~, _ BASF Akt~enge~ell~ch~ft 920400 O.Z. 0050/43411 43 2100~

No. Xlr~
384 3-C~H5 385 4~C/Hr~
386 2-(2'-F-C6H4) .
387 2-(3'-F-C6Hq) 388 2-(4'-F-C6H4) 389 3-(2'-F-C6H4) .
390 3-(3'-F-C6H4) 391 3-(4'-F-C6H4) , . . ..
392 4-(2'-F-C6H4) 393 4-(3'-F-C6H4) .. _ . . .
394 4-~4'-F-C6H4) 395 2-(2'-Cl-C6H4) 396 2-(3'-Cl-C6H4) 397 2-(4'-Cl-C6H4) 398 3-(2'-Cl-C6H4) _ ,.
399 3-(3'-Cl-C6H4) .
. _. 3-(4'-Cl-C6H4) 401 4-(2~-cl-C6~-) 402 4-(3'-Cl-C6H4) 403 4-(4'-Cl-C6H4) 405 2-(2'-CH3-C6H4) ,~ .. .
406 2-(3'-CH.-C6H4) _, 407 2-(4'-CH3-C6H4) 408 3-(2'-CH3-C6H4) 409 3-(3'-CH3-C6H4) 410 3-(4'-CH3-C6H4) 411 4-(2'-CH3-C6H4) ----- ..... ._ 412 4-(3'-CH3-C6H4) ._ . - .. .. _._ 413 4-(4~-cHl-c6H4) 414 2-(2'-CH3-CO-C6H4) 415 2-(3'-CH3-CO-C6H4) 416 2-(4'-CH3-CO-C6H4) 417 3-(2' <~ CC~C ~
418 3-(3'-CH3-CO-C6H4) 419 3-(4'-CH-~-CO-C~H4) 420 4-(2'-CH-.-CO-C~H4) _ BASF Akt~enge~ellachaft 920400 O.Z. 0050/43411 4~ 21~D~

No. Xm ...__.
421 4-(3'-CH~-CO-C6H4) 422 4-(4'-CHl-CO-C~,Hq) 423 2-(2'-(CH3-C(=NOallyl))-C6Hq) 424 2-(3'-(CH3-C(=NOallyl))-Ct,H4) 425 2-(4'-(CH3-C(=NOallyl))-C6H4) _ . .
426 3-(2~-(CH3-C(=NOallyl))-C~H4) 427 3-(3'-(CH3-C(=NOallyl))-C6H4) 428 3-(9'-(CH3-C(=NOallyl))-C6H4) .
429 4-(2'-(CH3-C(=NOallyl))-C6H4) 430 4-(3'-(CH3-C(=NOallyl))-C6H4) 431 . 4-(4'-(CH3-C(=NOallyl))-C6H4) 432 . 2-(2'-CH3O2C-C6H4) 433 2-(3'-CH3O2C-C6H4) 434 2-(4'-CH3O~C-C6H4) 435 3-(2'-CH3O~C-C6H4) .
436 3-(3'-CH3O2C-C6H4) -- _ . ~
- _ 3-(4'-CH3O2C-C6H4) 438 4-(2'-CH3O2C-C6H4) 439 4-(3'-CH3O2C-C6U4) 440 4-(4'-CH3O2C-C6H4) . ~
441 2-(2'-CH3O-C6H4) -.
442 2-(3'-CH3O-C6H4) . .
443 , 2-(4'-CH3O-C6H4) 444 3-(2~-CH~O-C~.H4) . .
445 3-(3'-CHlO-C6H4) .
446 3-(4~-CH3O-C6H4) _. _ . , ,, 447 4-(2~-CHlO-C6H4) .
448 4-(3'-CH3O-C6H4) 449 4-(4'-CH3O-C6H4) 450 2-(2'-O2N-C6H4) 451 2-(3'-O~,N-C6H4) .
452 2-(4l-O N-C6H4) ._ _ .
453 3-(2'-O2N-C6H4) . _ 454 3-(3'-O2N-C6H4) _ . _ . ,.~.
455 3-(4~-O,N-C,~H4) 456 4-(2~-O,,N-C~H4) _ BASF Akt~ensleElell8chaft 920400 0.2i . 0050/43411 2iO05~6 No ~ Xm _ ; _ _ 457 4- (3 ' -0~ N-C6H4) 458 4- (4 '-O2N-C6H4) 459 2- (2 '-NC-C6H4) 460 2- (3 ' -NC-C6H4) 461 2 - (4 ' -NC-C 6Hq ) 462 . 3- (2 ' -NC-C6H4) 463 3- (3 ' -NC-C6H4) 464 3- (4 '-NC-C6H4) 465 4 - ~ 2 ' -NC-C6H4) 466 4- (3 ' -NC-C6H4) _ 467 4 - (4 ' -NC-C6H4) 468 2- (2 ' -CF-~ -C6H4) . . . - . .
469 2- (3 ' -CF~-C6H4) ,,_ , _ 470 2 - (4 ' -CF3 -C 6H4) 471 3- (2 '-CF-~-C6H4) 472 3- (3 '-CF3-C6H4) ; ~ 3 (4 ~ -CF3 - ~`6H4) 474 4 - (2 ' -CF3 -C 6H4) 475 4- (3 '-CF3-C6H4) 476 4 - (4 ' -CF3 -C 6H 4) 477 2 --o-c6H5 475 3 -o-c6H5 476 4-O-C6Hs 478 - 2 -O- (2 ' -F-C6H4) 479 2-O- ~ 3 ' -F-C6H4) 480 ~
481 _ 3-O- ~ 2 ' -F-C6H4) 482 3 - O- (3 ' -F-C6H4) 483 3-O- ~4 '-F-C6H4) .
484 4-O- ~2 ' -F-C6H4) 485 4 -O- ~ 3 ' -F-C6H4) 486 4 -O- ~ 4 ' -F-C6H4) 487 2-O- (2 ' -Cl-Ci,H4) . ,._ 488 2-O- (3 ' -Cl-C~H4) 489 2 - O- (4 ' -C l -C ~H ~ ) .
490 3-O- (2 ' -Cl-C~.H4) . ._ BASF Aktien~eaellachaft 920400 O.Z. 0050/43411 46 21005~

No. Xl,, 491 3-O-(3'-Cl-C6H4) 492 3-O-(4'-Cl-C6H4) 493 3-0-(4'-Cl-C6H4) 494 4-O-(2'-Cl-C6H4) 495 4-o-(3'-Cl-C6H4) 496 4-o-(4'-Cl-C6H4) 497 2-O-(2'-CH3-C6H4) 498 2-O-(3'-CH3-C6H4) _ 499 2-O-(4'-CH3-C6H4) .
500 3-o-(2~-cH3--c6H4) 501 3-O-(3'-CH3-C6H4) 502 3-O-(4'-CH3-C6H4) 503 4-O-(2'-CHI-C6H4) 504 4-O-(3'-CH3-C6H4) 505 4-O-(4'-CH3-C6H4) .. .. . ..
506 2-O-(2'-CH3-CO-C6H4) 507 2-O-(3'-CH3-CO-C6H4) 508 2-O-(4'-CH3-CO-C6H4) 509 3-O-(2'-CH3-CO-C6H4) . ~
510 3-O-(3'-CH3-CO-C6H4) .
511 3-O-(4'-CH3-CO-C6H4) ~. . _ 512 4-O-(2'-CHl-CO-C6H4) . _ 513 4-O-(3'-CH3-Co-C6H4) : . _ 514 - 4-O-(4'-CH3-Co-C6H4) 515 2-O-(2'-(CH3-C (=NOallyl))-C6Hq) 516 2-o-(3~-(cH3-c(=Noallyl))-c6H4) 517 G (4 C~ r~ llyl ~ t,) 518 3-0-(2'-(C~ NO~IIYII~ L~
519 3-0-(3'-(CH3-C (=NOallyl))-C6H4) _ 520 3-0-(4'- (CHl-C(=NOallyl))-C~H4) . _ 521 4-0-(2'-( CHl-C(=NOallyl))-C6H4) 522 4-O-(3'-(CH3-C(=NOallyl))-C6H4) 523 _ . 4-O-(4'-(CHl-C(=NOallyl))-C6H4) 524 2-O-(2'-CH-,O~C-C6H4) 525 2-O-(3~-CH30,C-C~H4) .
526 2-O-(4'-CH-~O~C-C6H4) BASF Akt~en~esell~ch~St 920400 O.Z. 0050/43411 47 21 00~4~

NO. . . .
527 3-0-(2'-CH30 C-C6H4j 528 3-0-(3'-CH30 C-C~H9) ._ _ 3-O-(4'-CH3O2C-C6H4) 530 4-O-~2'-CH3O~C-C6Hq) 531 4~O~(3'~CH3O2C-C6Hq) 532 4-O-(4'-CH~O`C-C6H4) 533 2-O-(2'-CH3O-C6Hg) 534 2-O-(3'-CH3O-C6H4) 535 ~
536 3-O-(2'-CH3O-C6H4) 537 3-O-(3'-CH3O-C6Hq) 538 3-O-(4'-CH30-C6H4) 539 4-O-(2'-CH3O-C6H4) 540 4-O-(3'-CH3O-C6H9) 541 _ 4-O-(4'-CH30-C6Hg) 542 2-O-(2~-o2N-C6H4) 543 2-O-(3'-O2N-C6H9) 544 2-O-(4~-O2N-C6Hg) 545 3-0-(2'-O~N-C6Hq) 546 3-O-(3'-O2N-C6H4) 547 3-O-(4'-O2N-C6H4) _ .
548 4-o-(2~-o2N-c6H4) ~ 4-O-(3~-O2N-C6Hg) 550 - 4-O-(4'-O2N-C6Hg) 551 2-O-(2'-NC-C6H4) 552 2-0-(3'-NC-C6Hq) 553 2-O-(4'-NC-C6H4) 554 3-O-(2'-NC-C6H4) 555 3-0-(3'-NC-C6Hq) 556 3-0-(4'-NC-C6Hq) 557 4-O-(2'-NC-C6H4) 558 4-0-(3'-NC-C6Hg) 559 4-o-(4'-NC-C6H4) 560 2-O-(2'-CF3-C6Hg) 561 r 2-O-(3'-CF-~-C6H4) 562 2-O-(4'-CF~-C6H4) BASF Akti~n~e~ellschaft 920400 O.Z. 0050/43411 48 ~ 4 ~

No. X", 563 3-O-(2'-CF3-C6H4) 564 3-O-(3'-CF3-C6H4) 565 3-O-(4'-CF3-C6H4) .
566 4-0-(2'-CFI-C6H 4) . - , 567 4-O-(3'-CF3-C6H9) 568 4-O-(4'-CF~-C~.H4 ) 569 2-pyridinyl-2' 570 2-pyridinyl-3' 571 2-pyridinyl-4' 572 3-pyridinyl-2' 573 3-pyridinyl-3' . . _ . , 574 3-pyridinyl-4' . _ . _ , , , 575 4-pyridinyl-2' 576 4-pyrldinyl-3' 577 4-pyridinyl-4' 578 2-pyrimidinyl-2' 579 2-pyrimidinyl-3' 580 2-pyrimidinyl-4' _ . .
581 3-pyrimidinyl-2' 582 3-pyrimidinyl-3' 583 3-pyrimidinyl-4' 584 4-pyrimidinyl-2' 585 4-pyrlmidinyl-3' 586 - 4-pyrimidinyl-4' 587 2-pyrazolyl-1' 588 2-pyrazolyl-3' 589 2-pyrazolyl-4' 590 3-pyrazolyl-1~
591 3-pyrazolyl-3' 592 3-pyrazolyl-4~
593 4-pyrazolyl-1' 594 4-pyrazolyl-3' 595 4-pyrazolyl-4' 596 2-isoxazolyl-3' 597 2-isoxazolyl-4' 598 2-isoxazolyl-5' BAS~ AXtien~q~oll~c~t g20400 O.Z. 00$0~434~1 49 21~05~
I

__ No. X" ¦
... . ... ~ ... __ 599 3-i oxazolyl-3' 600 3-li oxazoiyi-4~
601 3-i. oxazoiyl-S' 60~ 4-ilsoxazolyl-3 .__ 604 4 i~oxazolyl-5 606 2-i~othi~zolyl-4 ._ 607 2~ oth~azolyl-5' .......... . . ... .....
~08 3-isothiazolyl-3 _ 609 3-i~othiazolyl-4 ~10, 3-i~othlazolyl-5 611' - -i -''-' 613 4-i~othiazolyl-5 .., 614 2-imidazolyl-1' 615 2-lmi~azolyl-2 617 3~imidazolyl-l' 618 3-imi~azolyl 61g 3-imidazolyl-4 ~

. _ 4~imidazoiyl-2' 622 - =
623 2-oxazolyl-2' 624 2-oxazolyl 4' . . . .
~25 2-oxazolyl-5' ,~., ~ ~_~
62~ 3-oxazolyl-a' ..
627 3-oxazolyl-4' 628 3~oxazolyl-S~
629 4-oxazolyl-2' 630 _ 631 4-oxazolyl-5' ~_ . _ . .
632 2-thiazolyl-2 .__ ~33 2-thiazolyl-~' 634 2-thiazolyl-5' _ ..... ... . ..

BASF A~tien~esell~cha~t 920400 O.Z. 0050/43411 ~No. X~, 635 3-thiazolyl-2' 636 3-thiazolyl-9' 637 3-thiazolyl-5' 638 4-thiazolyl-2' 639 4-thiazolyl-4' 640 4-thiazolyl-5' BASF Aktien~e~ell~ch~ft 920400 O.Z. 0050/43411 51 21~0~6 Table 2 ~ ~CH

H3CO2C ~ CH3 No. A
1 pyrrolyl-3 N-CHl-pyrroiyl-3 N-C~,H5-pyrrolyl-3 N-(9'-CH3-C6H4)-pyrrolyl-3 N-(3'-CH3-C6H4)-pyrrolyl-3 6 N-(2'-CH3-C6H4)-pyrrolyl-3 _ 7 N-(4'-CH3O-C6H4)-pyrrolyl-3 8 N-(3'-CH3O-C6H4)-pyrrolyl-3 . N-(2'-CH3O-C6H4)-pyrrolyl-3 . N-(g'-NO,-C6H4)-pyrrolyl-3 11 N-(3~-NO~-C6H4)-pyrrolyl-3 12 N-(2'-NO2-C6H4)-pyrrolyl-3 13 N-(4'-CN-C6H4)-pyrrolyl-3 14 N-(3'-CN-C6H4)-pyrrolyl-3 N-(2'-CN-C6H4)-pyrrolyl-3 16 N-(9'-Cl-C~H4)-pyrrolyl-3 17 . _ N-(3'-Cl-C5H4)-pyrrolyl-3 18 N-(2'-Cl-C6H4~-pyr-olyl-3 19 pyrrolyl-2 N-CH,-pyrrolyl-2 21 N-C~H5-pyrrolyl-2 22 N-(4'-CH~-Ct~H4)-pyrrolyl-2 23 ~
29 N-(2'-CH,-C6H4)-pyrrolyl-2 N-(9'-CH.O-C~H4)-pyrrolyl-2 ~ASF ~ktien~esellsch~ft 920400 O. Z . 0050/A3411 52 21~5~

. . , No. A
26 N-(3'-CH~0-C6H9)-pyrrolyl-2 27 N-(2'-CH30-C6H4)-pyrrolyl-2 28 N-(4'-N02-C6H4)-pyrrolyl-2 29 N-(3'-N0~-C~H4)-pyrroly1-2 N-(2'-N0~-C6H4)-pyrrolyl-2 31 N-(4'-CN-C6H4)-pyrrolyl-2 .

33 N-(2'-CN-C6H4)-pyrrolyl-2 34 N-(4'-Cl-C6H4)-pyrrolyl-2 N-(3'-Cl-C6H4)-pyrrolyl-2 36 N-(2'-Cl-C6H4)-pyrrolyi-2 37 furyl-2 38 5-CHl-furyl-2 39 ~
5-(4'-CHl-C6H4)-furyl-2 91 5-(3'-CH-I-C6H4)-furyl-2 42 5-(2'-CHl-C6H4)-furyl-2 93 5-(4'-CH30-C6H4)-furyl-2 94 5-(3'-CH30-C6Hq)-furyl-2 .,.__ . , , 5-(2'-CH30-C6H4)-furyl-2 ._ 46 5-(4'-N0~-C6H4)-furyl-2 ~. .
47 5-(3'-N02-C6Hg)-furyl-2 , , _ __ _ . _ 48 .
49 .. 5-(4'-CN-C6H4)-furyl-2 _ 5-(3'-CN-C~,H4)-fury1-2 51 5-(2'-CN-C6H4)-furyl-2 __ ..... . _~ .
52 5-(4'-Cl-C6H4)-furyl-2 . . ~
53 5-(3'-Cl-C6H4)-furyl-2 . __ . , 54 5-(2'-Cl-C6H4)-furyl-2 . . . _. --4-CHl-furyl-2 56 4-C,,H~,-fùryl-2 57 4-(4'-CHl-C~,H4)-furyl-2 58 4-(3'-CH,-C~H4)-furyl-2 59 4-(2'-CH-,.-ChH4)-furyl-2 4-(4'-CH30-C~,H4)-furyl-2 61 4-(3'-CH~0-C~.H~)-fury1-2 BASF Aktien~e~ell~chaft 920400 O.Z. 0050/43411 2100~46 No. A
62 4-(2'-CH-~O-C6H4)-furyl-2 63 4-(4'-NO,-Ct.H4)-furyl-2 64 . 4-(3'-NO.~-C6H4)-furyl-2 4-(2'-N0;-C~H4)-furyl-2 66 4-(4'-CN-C~H4)-furyl-2 67 4-(3'-CN-C6H4)-furyl-2 68 4-(2'-CN-C6H4)-furyl-2 69 4-(4'-Cl-C6H4)-furyl-2 4-(3'-Cl-C6H4)-furyl-2 71 4-(2'-Cl-C6H4)-furyl-2 _ - __ . . . . .
72 thieny1-2 73 5-CH3-thienyl-2 74 5-C,.Hr~-thienyl-2 5-(4'-CH3-C6H4)-thienyl-2 76 5-(3'-CH3-C6H4)-thienyl-2 77 5-(2'-CH3-C6H4)-thienyl-2 78 5-(4'-CH~O-C6H4)-thienyl-2 79 5-(3'-CHlO-C6H4)-thienyl-2 5-(2~-cH3o-c6H4)-thienyl-2 81 . 5-(4'-NO~-C6H4)-thienyl-2 82 .. __ 5-(3'-NO.-C6H4)-thienyl-2 ~83 5-(2'-NO -C6H4)-thienyl-2 84 5-(4'-CN-Ct,H4)-thienyl-2 - 5-(3'-CN-C~,H4)-thienyl-2 86 5-(2'-CN-C~H4)-thienyl-2 ~ _ , __ 87 5-(4'-Cl-C6H4)-thienyl-2 ~ _ , 88 5-(3'-Cl-C6H4)-thienyl-2 . . _ 89 5-(2'-Cl-C6H4)-thienyl-2 .
4-CHl-thienyl-2 . - . _ ~ , , 91 4-C~.H.. -thienyl-2 92 . 4-(4'-CH?=C6H4)-thienyl-2 93 4-(3'-CHl-C6H4)-thienyl-2 94 4-(2'-CH,-C6H4)-thienyl-2 4-(4'-CH~O-C6H4)-thienyl-2 96 4-(3'-CH,O-C~H4)-thienyl-2 97 4-(2'-CH~O-C~H4)-thienyl-2 BASF A~tion~e~ellBchaft 920400 O.Z. 0050/43411 2100~

: ~ _ No. A
98 4-(4'-NO,-Cf.H4)-thienyl-2 99 4-(3'-NO -C6H4)-thienyl-2 100 4-(2~-NO~-C6Hq)-thienyl-2 101 - - 4-(4'-CN-C6Hg)-thienyl-2 102 4-(3'-CN-C6Hq)-thienyl-2 103 4-~2'-CN-C6Hg)-thienyl-2 104 4-(4'-Cl-C6H9)-thieny1-2 105 4-(3'-Cl-C6Hq)-thienyl-2 106 4-(2'-Cl-C6Hq)-thienyl-2 107 thienyl-3 108 5-CH,-thienyl-3 .
109 5-C,-,Hr;-thienyl-3 , , . ......... . ___ 110 . 5-(4'-CH3-C6Hq)-thienyl-3 111 5-(3'-CH-,-C6Hq)-thienyl-3 112 5-(2'-CH~-C6Hq)-thienyl-3 113 5-(4'-CH3O-C6Hg)-thienyl-3 114 5-(3'-CH30-C6Hç)-thienyl-3 115 5-(2'-CH30-C6Hg)-thienyl-3 116 5-(4'-NO2-C6Hg)-thienyl-3 117 5-(3'-NO~-C6H4j-thienyl-3 118 5-(2'-NO~-C6Hg)-thienyl-3 119 5-(4'-CN-CfH4)-thienyl-3 120 .. 5-(3'-CN-C6H4)-thienyl-3 . . .
121 - 5-(2'-CN-C6Hq)-thienyl-3 122 5-(4'-Cl-C6Hg)-thienyl-3 123 5-(3'-Cl-C6Hq)-thienyl-3 124 5-(2'-Cl-C6H4)-thienyl-3 125 pyrazolyl-4 126 N-CH1-pyrazoly1-4 .
127 N-C,.H~,-pyrazolyl-4 128 N-t4'-CH,-ChH4)-pyrazolyl-4 .
129 N-(3'-CH3-C6H4)-pyrazolyl-4 . -130 N-(2'-CH,-C6H4)-pyrazolyl-4 . ._ 131 N-(4'-CH~O-C~,H~)-pyrazolyl-4 . , , __ 132 N-(3'-CH~O-Cf,H.;)-pyrazolyl-4 . , .
133 N-(2'-CHIO-C~.H.~,)-pyrazolyl-4 BASF Akti~ngeBellachaft 920400 O.Z. 0050/43411 2100~4~

No. A
134 N-(4~-N0,-C~,H4)-pyrazolyl-4 135 N-(3'-N0~-C6H4)-pyrazolyl-4 136 N-(2'-N0,-C6H4)-pyrazolyl-4 137 N-(4'-CN-C6H4)-pyrazolyl-4 138 . N-(3'-CN-C6H4)-pyrazolyl-4 139 N-(2'-CN-C6H4)-pyrazolyl-4 140 N-(4'-Cl-C6H4)-pyrazolyl-4 141 , N-(3'-Cl-C6H4)-pyrazolyl-4 142 N-(2'-Cl-C6H4)-pyrazolyl-4 143 3-CH,-N-methylpyrazolyl-4 144 _ _ 3-C6H5-N-methylpyrazolyl-4 145 3-(4'-CH,~-C6Hq)-N-methylpyrazolyl-4 146 3-(3'-CH~/-C6H4)-N-methylpyrazolyl-4 .
147 3-(2'-CH,-C6H4)-N-methylpyrazolyl-4 148 3-(4'-CH30-C6H4)-N-methylpyrazolyl-4 149 3-(3'-CH30-C6H4)-N-methylpyrazolyl-4 150 3-(2'-CH,0-C6H4)-N-methylpyrazolyl-4 151 3-(4'-~0 -C6~4)-N-methylpyrazolyl-4 -- . .. . ... . _ 152 3-(3'-N0~-C6H4)-N-methylpyrazolyl-4 153 3-(2'-N0 -Cf,H4)-N-methylpyrazolyl-4 154 3-(4'-CN-CbH4)-N-methylpyrazolyl-4 155 3-(3'-CN-C~,H4)-N-methylpyrazolyl-4 156 3-(2'-CN-C6H4)-N-methylpyrazolyl-4 157 3-(4'-Cl-C6H4)-N-methylpyrazolyl-4 158 3-(3'-Cl-C6H4)-N-methylpyrazolyl-4 .. 3-(2'-Cl-C6H4)-N-methylpyrazolyl-4 160 isoxazolyl-5 161 3-CH,,-isoxazolyl-5 162 3-C.. H,~-isoxazolyl-5 163 3-(4'-CHl-C6H4)-isoxazolyl-5 164 3-(3'-CH3-C6H4)-isoxazolyl-5 165 3-(2'-CHl-C6H4)-isoxazolyl-5 - , . ~
166 3-(4'-CH70-Cf,H4)-isoxazolyl-5 167 3-(3'-CH~0-C~H4)-isoxazolyl-5 ~ . ~ .
168 3-(2~-CH,0-C6H4)-isoxazolyl-5 .
169 3-(4'-N0.,-C(,H4)-isoxazolyl-5 . . _ , . .

BASF Aktiengeaell~chaft 920400O.Z. 0050/43411 562100~

No . A
170 3-(3'-NO~-C6H4)-isoxazolyl-5 171 . 3-(2'-NO~-C6H4)-isoxazolyl-5 172 3-(4'-CN-C6H4)-isoxazolyl-5 173 3-(3'-CN-C6H4)-isoxazolyl-5 174 3-(2'-CN-C6H4)-isoxazolyl-5 175 3-(4'-C1-C6H4)-isoxazolyl-5 176 3-(3'-Cl-C6H4)-isoxazolyl-5 177 3-(2'-Cl-C~H4)-isoxazolyl-5 178 4-chloroisoxazolyl-5 179 3-CHl-4-chloroisoxazolyl-5 180 3-CsHs-4-chloroisoxazolyl-5 181 3-(4'-CH3-C6H4)-4-chloroisoxazolyl-5 182 3-(3'-CHl-C6H4)-4-chloroisoxazolyl-5 183 3-(2'-CH~-C6H4)-4-chloroisoxazolyl-5 18q 3-(4'-CH3O-C6H4)-4-chloroisoxazolyl-5 185 3-(3'-CH3O-C6H4)-4-chloroisoxazolyl-5 186 3-(2~-CH 10-C6H4)-4-chloroisoxazolyl-5 . . . .
187 3-(4'-NO2-C6H4)-4-chloroisoxazolyl-5 188 3-(3'-NO2-C6H4)-4-chloroisoxazolyl-5 189 3-(2'-NO2-C6H4)-4~ hloroisoxazolyl-5 190 3_ ~
~ . .
191 3-(3'-CN-C6H4)-4-chloroisoxazolyl-5 192 3-(2'-CN-C6H4)-4-chloroisoxazolyl-5 193 - 3-(4'-Cl-C6H4)-4-chloroisoxazolyl-5 194 3-(3'-Cl-C6H4)-4-chloroisoxazolyl-5 195 3-(2'-Cl-C6H4)-4-chloroisoxazolyl-5 196 isoxazolyl-3 197 5-CH~-isoxazolyl-3 198 5-C,.Hs-isoxazolyl-3 199 5-(q'-CH.-ChH4)-isoxazolyl-3 200 5-(3'-CH,-C6H4)-isoxazolyl-3 201 5-(2'-CH~-C6H4)-isoxazolyl-3 202 5-(4'-CH30-C~H4)-isoxazolyl-3 203 5-(3'-CHlO-C6H4)-isoxazolyl-3 204 .~_ 5-(2'-CH~O-C6H4)-isoxazolyl-3 205 . 5-(qi-NO -C6H4)-isoxazolyl-3 BASF ~ktien5leBe11~::haft 920400 O.Z. 0050/43411 57 2100~)46 NO . ¦ A
206 5-(3'-NO~-C6H4)-isoxazolyl-3 207 5-(2'-NO~-C6H4)-isoxazolyl-3 208 5-(4'-CN-C6H4)-isoxazolyl-3 .
209 5-(3'-CN-C6H4)-isoxazolyl-3 210 5-(2'-CN-C6H4)-isoxazolyl-3 211 5-(4'-Cl-C6H4)-isoxazolyl-3 212 5-(3'-Cl-C6H4)-isoxazolyl-3 213 5-(2'-Cl-C6H4)-isoxazolyl-3 214 isothiazolyl-S
215 3-CH3-isothiazolyl-S
. _ , _ 216 3-ChHs-isothiazolyl-S
217 3-(4'-CH3-C6H4)-isothiazolyl-5 218 3-(3'-CH3-C6H4 ) -i sothiazolyl-5 219 3-(2'-CH~-C6H4)-isothiazolyl-5 220 3-(4'-CH~O-C6H4)-isothiazolyl-5 221 3-(3~-CH-~O-C6H4 ) -iSOthiaZO1Y1-5 222 3-(2'-CH3O-C6H4)-isothiazolyl-5 223 3-(4'-NO2-C6H4)-isothiazolyl-5 224 3-(3'-NO~-C6H4)-isothiazolyl-S
225 3-(2'-NO2-C6H4)-isothiazolyl-S
226 . 3-(4'-CN-C6H4)-isothiazolyl-S
227 . 3-(3'-CN-C6H4)-isothiazolyl-S
228 - 3-(2'-CN-C6H4)-isothiazolyl-5 229 3-(4'-Cl-C6H4)-isothiazolyl-5 230 3-(3'-Cl-C6H4)-isothlazolyl-5 231 3-(2'-Cl-C6H4)-isothiazolyl-5 . _ 232 oxazolyl-4 . . __ 233 2-CH3-oxazolyl-4 . ___ 2~Cr~H~~OXaZOiyl~4 235 2-(4'-CHl-C6H4)-oxazolyl-4 236 2-(3'-CH3-C6H4 ) -OXaZO1Y1-4 237 2-(2'-CHl-C6H4)-oxazolyl-4 238 ~- 2-(4~-CH-1O-Cf H4 ) -OXaZO1Y1-4 239 2-(3'-CH ~O-C~ H4 ) -OXaZO1Y1-4 240 2-(2'-CH3O-Ct,H4)-oxazolyl-4 241 2-(4'-NO -CfH~)-oxazolyl-4 BASF Aktien~eaQllachaft 920400 O.Z. 0050/43411 58 2100a~6 ~ _ .
No. A __ 242 2-(3'-NO;~-C6Hg)-oxazolyl-4 243 2-(2'-NO~-C6H4)-oxazolyl-4 244 . 2-(4'-CN-C6Hg)-oxazolyl-4 245 2-(3'-CN-C6Hg)-oxazolyl-4 246 2-(2~-CN-C6H4)-oxazolyl-4 247 2-(4'-Cl-C6H4)-oxazolyl-4 248 2-(3'-Cl-C6Hq)-oxazolyl-4 249 2-(2'-Cl-C6Hg)-oxazolyl-4 250 thiazolyl-4 251 2-CH3-thiazolyl-4 252 2-C6H5-thiazolyl-4 253 2-(4'-CHl_C6H4)-thiazolyl-4 254 2-(3'-CH3-C6Hg)-thiazolyl-4 255 2-(2'-CH3-C6Hg)-thiazolyl-4 256 . 2-(4'-CH3O-C6Hg)-thiazolyl-4 267 2-(3'-CHlO-C6Hg)-thiazolyl-4 258 2-(2'-CH30-C~Hg)-thiazolyl-4 _ 259 2-(4'-NO;.-C6Hg)-thiazolyl-4 260 2-(3'-NO~-C6Hg)-thiazolyl-4 261 2-(2'-NO,-C6Hg)-thiazolyl-4 262 2-(4~-cN-c6H9)-thiazolyl-4 263 2-(3'-CN-C6Hg)-thiazolyl-4 . . . . .
264 2-(2'-CN-C6Hg)-thiazolyl-4 265 - 2-(4'-Cl-C~Hg)-thiazolyl-4 .
266 2-(3'-Cl-C6Hg)-thiazolyl-4 .
267 2-(2'-Cl-C6H4)-thiazolyl-4 -- . ., _ .

268 N-CH3-1,2,4-triazolyl-5 269 3-CH,!-N-CH3-1,2,4-triazolyl-5 .. _ .. ~
270 3-ChH5-N-CH3-1,2,4-triazolyl-5 .
271 3-(4'-CH3-C6H4)-N-CH3-1,2,4-triazolyl-5 272 3-(3'-CHl-C6Hg)-N-CH3-1,2,4-triazolyl-5 273 . 3-(2'-CH~-C~H4)-N-CH,-1,2,4-triazolyl-5 274 3-(4'-CH10-C~H4)-N-CH-~-1,2,4-triazolyl-5 275 _ 3-(3'-CHlO-C~H4)-N-CH3-1,2,4-triazolyl-5 276 3-(2'-CH~O-C6H4)-N-CHI-1,2,4-triazolyl-5 277 3-(4'-NO~-C~H4)-N-CH-I-1,2,4-triazolyl-5 BASF Aktien~esell~chaft 920400 O.Z. 0050/43411 59 2100a4~

_ .
No. A
278 3-(3'-NO -C6Hq~-N-CH~-1,2,4-triazolyl-5 279 3-(2'-NO~-C6H4)-N-CH3-1,2,4-triazolyl-5 280 3-(4'-CN-C6H4)-N-CH3-1,2,4-triazolyl-5 281 -(3'-CN-C6H9)-N-CH3-1,2,4-triazolyl-5 . -282 -(2'-CN-C6Hq)-N-CH3-1,2,4-triazolyl-5 283 3-(4'-C1-C6Hq)-N-CH3-1,2,4-triazolyl-5 284 3-(3'-Cl-C6Hq)-N-CH~-1,2,4-triazolyl-5 285 -(2'-Cl-C6H4)-N-CH3-1,2,4-triazolyl-5 286 1,3,4-oxadiazolyl-2 287 5-CH3-1,3,4-oxadiazolyl-2 288 -C6H5-1,3,4-oxadiazolyl-2 289 5-(4'-CH3-C6H4)-1,3,4-oxadiazolyl-2 290 5-(3'-CH3-C6H4)~1,3,4-oxadiazolyl-2 . _ .
291 5-(2'-CH3-C~H4)-1,3,q-oxadiazolyl-2 292 5-(4'-CH30-C6H4)-1,3,4-oxadiazolyl-2 293 5-(3'-CH30-C6H4)-1,3,4-oxadiazolyl-2 294 5-(2'-CH30-C6Hq)-1,3,4-oxadiazolyl-2 296 . 5-(3'-NO2-C6Hq)-i,3,4-oxadiazolyl-2 297 5-(2'-NO~-C6Hq)-1,3,4-oxadiazolyl-2 298 5-(4'-CN-C6Hq)-1,3,4-oxadiazolyl-2 299 5-(3'-CN=C6Hq)-1,3,4-oxadiazolyl-2 300 5-(2'-CN-C6H4)-1,3,4-oxadiazolyl-2 301 ~ 5-(4'-Cl-C6Hq)-1,3,4-oxadiazolyl-2 302 5-(3'-Cl-C6Hq)-1,3,4-oxadiazolyl-2 303 5-(2'-Cl-C6H4)-1,3,4-oxadiazolyl-2 304 1,2,4-oxadiazolyl-3 305 5-CH3-1,2,4-oxadiazolyl-3 306 5-C~.HI,-1,2,4-oxadiazolyl-3 _ 5-(4'-CHl-C~H4)-1,2,4-oxadiazolyl-3 308 5-(3'-CH3-C6Hq)-1,2,4-oxadiazolyl-3 309 5-(2'-CH3-C6H4)-1,2,4-oxadiazolyl-3 310 5-(4'-CH30-C6Hq)-1,2,4-oxadiazolyl-3 311 5-(3'-CH-10-C6Hq)-1,2,4-oxadiazolyl-3 312 5-(2'-CH-IO-C6Hq)-1,2,4-oxadiazolyl-3 313 5-(4'-NO~-C6Hq)-1,2,4-oxadiazolyl-3 BASF Aktiengesell~ch~ft 920400 O.Z. 0050/43411 2100~46 r No. A
314 5-(3'-NO~-C6H4)-1,2,4-oxadiazolyl-3 31S 5-(2'-NO~-C6H4)-1,2,4-oxadiazolyl-3 316 5-(4'-CN-C6H4j-1,2,4-oxadiazolyl-3 317 5-(3'-CN-C~.H4)-1,2,4-oxadiazolyl-3 318 . 5-(2'-CN-C6H4)-1,2,4-oxadiazolyl-3 .
319 5-(4'-Cl-C6H4)-1,2,4-oxadiazolyl-3 320 5-(3'-Cl-C6H4)-1,2,4-~xadiazolyl-3 321 5-(2'-Cl-C6H4)-1,2,4-oxadiazolyl-3 322 1,2,4-oxadiazolyl-5 323 3-CHl-1,2,4-oxadiazolyl-5 324 3-C~H5-1,2,4-oxadiazolyl-5 325 3-(4~-CH3-C6H4)-1,2,4-oxadiazolyl-5 326 3-(3'-CH3-C6H4)-1,2,4-oxadiazolyl-5 327 3-(2'-CHI-C6H4)-1,2,4-oxadiazolyl-5 328 3-(4'-CHlO-C6H4)-1,2,4-oxadiazolyl-5 329 3-(3'-CH,O-C6H4)-1,2,4-oxadiazolyl-5 330 3-(2'-CH~O-C6H4)-1,2,4-oxadiazolyl-5 331 3-(4'-NO2-C6H4)-1,2,4-oxadlazolyl-5 332 . 3-(3'-NO2-C6H4)-1,2,4-oxadiazolyl-5 333 3-(2'-NO2-C6H4)-1,2,4-oxadiazolyl-5 334 3-(4'-CN-C6H4)-1,2,4-oxadiazolyl-5 335 3-~3'-CN-C6H4)-1,2,4-oxadiazolyl-5 336 ,-, 3-(2'-CN-C6H4)-1,2,4-oxadiazolyl-5 337 - 3-(4'-Cl-C6H4)-1,2,4-oxadiazolyl-5 338 3-(3'-Cl-C6H4)-1,2,4-oxadiazolyl-5 339 3-(2'-Cl-C6H~)-1,2,4-oxadiazolyl-5 .~ 1,2,4-thiadiazolyl-3 341 5-CH3-1,2,4-thiadiazolyl-3 342 5-C,.Hr,-1,2,4-thiadiazolyl-3 343 5-(4'-CHl-C6H4)-1,2,4-thiadiazolyl-3 344 5-(3'-CH~-C6H4)-1,2,4-thiadiazolyl-3 345 5-(2'-CH,-C6H4)-1,2,4-thiadiazolyl-3 346 5-(4'-CH~O-C~H4)-1,2,4-thiadiazolyl-3 347 5-(3'-CH,O-C~,H4)-1,2,4-thiadiazolyl-3 348 5-(2'-CH~O-C6Hq)-1,2,4-thiadiazolyl-3 349 5-(4'-NO,-ChH4)-1,2,4-thiadiazolyl-3 ~ASF Akt~on~e~ollschaft 920400 O.Z. 0050/43411 61 2100~4~

Nc. A
350 5-(3'-NO~-C~H4)-1,2,4-thiadiazolyl-3 .
351 _ 5-(2'-NO~-C6H4)-1,2,4-thiadiazolyl-3 352 5-(4'-CN-C6H4)-1,2,4-thiadiazolyl-3 353 5-(3'-CN-C6Hq)-1,2,4-thiadiazolyl-3 354 5-(2'-CN-C6H4)-1,2,4-thiadiazolyl-3 355 5-(4'-Cl-C6H4)-1,2,4-thiadiazolyl-3 356 5-(3'-C1-C6H4)-1,2,4-thiadiazolyl-3 357 5-(2'-C1-C6H4)-1,2,4-thiadiazolyl-3 358 1,3,4-thiadiazolyl-2 359 5-CHl-1,3,4-thiadiazolyl-2 360 ~ 5-C6Hs-1,3,g-thiadiazolyl-2 361 5-(4'-CH3-C6H4)-1,3,4-thiadiazolyl-2 362 5-(3'-CH3-C6H4j-1,3,4-thiadiazolyl-2 363 . 5-(2'-CHI-C6H4)-1,3,4-thiadiazolyl-2 364 5-(4'-CH30-C6H4)-1,3,4-thiadiazolyl-2 365 ~
366 _ 5-(2'-CH30-C6H4)-1,3,4-thiadiazolyl-2 367 5-(4'-NO~-C6H4)-1,3,4-thiadiazolyl-2 368 5-(3'-NO2-C6H4)-1,3,4-thiadiazolyl-2 369 5-(2'-NO2-C6H4)-1,3,4-thiadiazolyl-2 370 5-(4'-CN-C6H4)-1,3,4-thiadiazolyl-2 371 5-(3'-CN-C6H4)-1,3,4-thiadiazolyl-2 372 5-(2'-CN-C6H4)-1,3,4-thiadiazolyl-2 373 . 5-(4~-Cl-C6H4j-1~3~4-thiadiazolyl-2 374 5-(3'-Cl-C6H4)-1,3,q-thiadiazolyl-2 376 pyridlnyl-2 377 pyridinyl-4 378 ~ _ 380 pyridazinyl-2 381 pyrimidinyl-4 . . ._ , , 382 pyrimidinyl-5 , , , _................... _ , 383 pyrimidinyl-2 334 pyridinyl-3 -- . . . , _ BASF Aktien~esellschaft 920400 O.Z. 0050/43411 62 21~0~46 Table 3 IR( cm~l )or No. CompDu~d . m p H-NMR ~ ppI ) _ 7.5 (s, I ~1); 3.8 (s, 3 H);
~0~ ~ 3.65 (s, H) _ ~ ~ ~ 6.6 (s, l H); 3.9 (s, 3 H);

i ~ C113 ~ ~ CI 6.6 (s, I H); 3.9 (s, 3 H);

4 H3C02C~ ~~ 3.7 (s, 3 H) ~ CH3 ,...~
~C~ K~

BASF Akt~ençl08elll~chaft 920400 O. æ . 0050/43411 63 210054~

No. ~ompound IR( cm~I )or _ IH--NM~ ( PP,n ) ~1 ~O~CH3 ~ 76 7 ...._ _ . 63 ~13CO2C ~C~3 _ . . . 7 5 (5, 1 H); 3.8 (5, 3 H);
8 ~0~ CH3 3 7 (5~ 3 H) H3CO2CJ~ ~CH3 ~

~ 6.55 (5,1 H); 3.9 (5, 3 H);
9 ~CH3 3,7 (S~ 3 ~I) _ __ .
~ 7,5 (5, I H); 3.8 (5, 3 H);
~O~~O~N 3.7 (5, 3 ~) __ H3CO2CJ~ ~C~l3~3 , BASF Alctiengegell8chaft 920400 O. Z . 0050/43411 64 210~

: _ _ Nn. Compound IR ( cm~l 3 or m p ~ NMR ( PP~ 1 . .

11 ~O--~N CH3 67 H3CO2C ~CH3 ~01 _ _ 13 H3CO ~C(~ ~ 82 . , . _ _ _ 14 ~O~ 125 C~C ~CH3N =~ D

BASF Aktien~e~ellschaft 920400 O.Z. 0050/43411 2100~

. . _ la( cm~~ )or No. Conipound III--NMR ( PP,n ~ m p .. _ 16 ~0~ ~0 3 57 (s 3 H); 3.8 (s, 3 H);

.. .. .

17 ~`~3 3 7 (s 3 HH); 3-8 (s, 3 H);

_ ~0 ~3 _ _ 76 H3C02C C~3 . . . . ~ .

19 ~O~N~0 179 H3C02C O~CH3 ~E ~ ~ ~0 116 BASF Akt~enge~ellschaft 920400 O.Z. 0050/43411 66 21 003~ ~

IR ( cm~ I ) or _ No. Compound m p IH-NMR ( PPn"

1 ~3CO~C~ ~CH3 . .
~ 7.5 (s, I H); 3.75 (s, 3 H);
22 ~O~N 3.65 (s, 3 H) H3C02C~ '~ CH3~
_ . _ 3~ N

. ~ 7.55 (s, I H); 3.8 (s, 3 H);
24 b~o~~ 3.65 (s, 3 H) H3CO~C~ ~CH3 ~
_ . . ,, . ,_ ~5 ~3CO2C~O~ _ 123 BASF Aktien5J~sell~chaft 920400 O.Z. 005n/43411 67 2100a~

No.Compound IR ( cm~ I ) or m p __ IH--~MR ( PP~ ) ~ 2 isomers (approx. 3 1):
26 ~ ~NO--CH~ 7.5 (2 s, I H); 3.8 (2 s, 3 H);
J~ O C113 l l 3.65(2s,3H
H3C02C -- ~CH3 ~
.
H3CO--N~
27 ~oJ 74 ~ 13C02C~ ~ CH3 28 }i3C02C~

, . . . - .
. ~ 7.55 (s, l H); 3.8 (s, 3 H);

29 H3C02C~ 3,7 (s, 3 H) _ ~

~ ~~ 3.65 (s, 3 H) H3C02C~~C113 . . .

BASF Aktien~el3ell1aCh~ft 920400 0 . Z . 0050/43411 68 2 ~ 0 ~

IR( cm~I )or No. Compound lH-NMR ( ppm ) m p _ ~7 45 (~, I II); 3.8 (s, 3 H);

H3CO2C O~CH3 . _ ~ ~l6.5 (s, I H); 3.85 (s, 3H);
32 ~O~ 3.65 (s, 3 H) ~3C02C~ .

33 H3CO2C~ CH3 ~ 123 , , ,,,~ .. ,.. _ ~; 13 (sjI H) 3.73 (~, 3 tl);

~ ~ 3 7 (s~ 3 H) ~ ~N ~J 96 _ H3CO2C CH3 BA8F Akti~nge~ellsch~ft 920400 O.Z. 0050/43411 69 210~

IR ( cm~l ) or No. Compound m p IH-NMR ( ppm ) .

i~

37 H3C()zC~ ~CH~ cl _ f ~ ~ CH3 7 A5 (s, 1 H); 3.75 (s, 3 H);
38 ~O~ 3.65 (5~ 3 H) .. ,__ ___ . . .. - _ _ . ~ ~ 7.45 (s~ I H); 3.8 (s, 3 H);
39 ~ CH3 3.65 (s~ 3 H) H3COzC CH3 . . . __ ~ CH3 ~l 7.5 (s~ I H); 3.8 (s, 3 H);
~OJ~ 38 (s~ 3 H) H3CO2C ~ CH3 _ BASF A~ctien~esellEIchaft 920400 O . Z . 0050/43411 210054~

IR( em~l )or NQ Compound IH-NMR ( PP~ ~ m p . - .

41 H3Co2c~o~ N--N 106 ~ c~oo~

~ OCI13 7.45 (s, IH); 3.75 (s, 3H);
43 ~ ~ 3.7 (s, 3H); 3.6 (s, 3H) H3C02C~O~CH3 -- e~ 7.46 (s, l l l); 3.75 (s, 3H); .
44 ~~ 3.6(s,3~) ~~`3~

BASF Alctien~esellschaft 920400 O. Z . 0050/43411 71 2103~

No, ¦ CODIPOU--d ~ NMR ( pp ) F3p I 1 ¦ H 7.6 (s, I H); 3.9 (s, 3H);
46 ~~ ~0 3.8 (s, 3H) H3C02C ~CH3 . .

47 ~o~J~ 7.45 (s, IH); 3.75 (s, 3H);

H3C02C~ ~ ~ CH 3.65 (s, 3H); 3.35 (s, 3H) 48 ~0~ 98 H3C02C 0~CH30 49 . 3.6 (~ 3H) H3C02C~ ~CII~
~ CH3 _ . _ sn ~O ~N 16~
~3C02C~O~C~13 ~ ~

_ ~ . ~

BASF A)ctiengesell~cha~t 920400 O.Z. 0050/43411 72 2~

No. C-mpou~d IR ( cm~ I ) or m p ~[~=11 ~ ~ ~CH3 -1 ~ ,~ 1 ~ ~ O~-~Cl 1l9 BASF Aktien~e~ellschaft 920400 O.Z. 0050/43411 73 ~10~4~

No. Compound IR ( cm~ I ) or m _ __ IH-NMR( PP~ ) P
__ .

56 ~0~N 1 17 H3CO2C ~CH3 ~3 _ .

57 ~0~ N 97 113CO2C ~CH3 ~ _ 1~ 7 6 (s, IH); 3.8 (s, 3H);
58 ~O~¢N

. . _ 59 ~O~N 128 3 2 Ci~3 CH3 ~) _ H3C02~ CH3 _ BASF Aktien~eAell~Chaft 920400 O. Z . 0050/43411 74 21~0~6 No. Cou~pound III-NMA ( PP ) m p _ .

L~ CIIIC~ ~C ~ H3 82 6:~ ~ I 115 H3CO~C ~

6S ~0 O _ H3C02C ~ ~ - ... __.

BASF ~ktienge8ellgchaft 920400 O.Z. û050/43411 21G0~46 IR ( cm~ I ) or NO. CODIPDUnd m p IH-~MR ~ ppm ) .. ._ - _ _ 66 ~O--~ ` O 135 H3CO2C ~CH3 ~3~ CH3 . . __ - . . ,. __ . _ _ 67 ~l3co2c~ ~ ~ 3 6 I c;, 3H ) _ 68 [~ C ~ I 7 . 4 ( s, 3 H ), ~ ~o~N~l 1~8 1~ .

BASF Aktien~e~ell~ch~lft 920400 O.Z. 0050/43411 76 2100~4~

IR ( cm~7 ) or _ NQ Compound IU-t~MR ( PP~ ) m p 71 ~O~ç 3 8 ( s, 3 H ), H3CO2C O~CH3 7 .45 Is, lH);

72 ~0~ ) ) CH3 73 ~ ~ÇN ~ 3 6 5 I s, 3 H ), H3CO2C ~ CH3 . . ; .5 (s, lH); _ 74 ~ ~ÇN ~ 3 6 5 ( 6, 3 H );

H3CO2C ' ~CH3 ~0 116 H3CO2C ~CH3 . .

BASF A~cti~ngesellccha~t 920400 O . Z . 0050/43411 77 21~0~46 No. Compound IX ( cm~ I ) or IU-~MR ( PP~ ) rn . ~ _ - . _ 76 ~ ~N~3 118 H3C02C ~ CH3 ~ ~ S ~ R, I U ) ~

C~3 _ 2~ Cl ~

~ BASF Aktien~esellachaft 920400 O.Z. 0050/43411 \

2100~

The novel compounds are suitable as fungicides.
The fungicidal compounds according to the invention, or agents containing them, may be applied for instance in the form of directly sprayable solutions, powders, suspensions (including high-percentage aqueous, oily or other suspen-sions), dispersions, emulsions, oil dispersions, pastes, dusts, broadcasting agents, or granules by spraying, atomiz-ing~ dusting, broadcasting or watering. The forms of ap-plication depend entirely on the purpose for which the agents are being used, but they must ensure as fine a distribution of the active ingredients according to the invention as possible.
Normally, the plants are sprayed or dusted with the active ingredients or the seeds of the plants are treated with the active ingredients.
The formulations are produced in known manner, for example by extending the active ingredient with solvents and/or carriers, with or without the use of emulsifiers and disper-sants; if water is used as solvent, it is also possible to employ other organic solvents as auxiliary solvents. Suit-able auxiliaries for this purpose are solvents such asaromatics (e.g., xylene), chlorinated aromatics (e.g., chlorobenzenes), paraffins (e.g., crude oil fractions), alcohols (e.g., methanol, butanol), ketones (e.g., cyclohex-anone), amines (e.g., ethanolamine, dimethylformamide), and water; carriers such as ground natural minerals (e.g., kaolins, aluminas, talc and chalk) and ground synthetic minerals (e.g., highly disperse silica and silicates);
emulsifiers such as nonionic and anionic emulsifiers ~e.g., polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates); and dispersants such as lignin-sulfite waste liquors and methylcellulose.
Examples of surfactants are: alkali metal, alkaline earth metal and ammonium salts of aromatic sulfonic acids, e.g., ligninsulfonic acid, phenolsulfonic acid, naphthalenesul-fonic acid and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl and alkylaryl sulfonates, and alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated BASF Aktien~esellschaft 920400 O.Z. 0050/43411 79 21~0~S

hexadecanols, heptadecanols, and octadecanols, salts of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctyl-phenol, ethoxylated octylphenol and ethoxylated nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropy-lene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin-sulfite waste liquors and methyl cellulose.
Powders, dusts and broadcasting agents may be prepared by mixing or grinding the active ingredients with a solid carrier.
Granules, e.g., coated, impregnated or homogeneous granules, may be prepared by bonding the active ingredients to solid carriers. Examples of solid carriers are mineral earths such as silicic acids, silica gels, silicates, talc, kaolin, attapulgus clay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, and ureas, and vegetable products such as grain meals, bark meal, wood meal, and nutshell meal, cellulosic powders, etc.
Examples of formulations are given below.
I. A solution of 90 parts by weight of compound no. 1 from Table 3 and 10 parts by weight of N-methyl-a-pyrrolidone, which is suitable for application in the form of very fine drops.
II. A mixture of 20 parts by weight of compound no. 2 from Table 3, 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, and 5 parts by weight of the adduct of 40 moles of ethylene oxide and BASF Alctien~esellschaft 920400 O.Z. 0050/43411 210~4S

1 mole of castor oil. By finely dispersing the mixture in water, an aqueous dispersion is obtained.
III. An aqueous dispersion of 20 parts by weight of com-pound no. 3 from Table 3, 40 parts by weight of cyclohexa-none, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil.
IV. An aqueous dispersion of 20 par~s by weight of compound no. 4 from Table 3, 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction having a boiling point between 210 and 280'~C, and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil.
V. A hammer-milled mixture of 80 parts by weight of com-pound no. 5 from Table 3, 3 parts by weight of the sodium salt of diisobutylnaphthalene-~-sulfonic acid, 10 parts by weight of the sodium salt of a lignin-sulfonic acid obtained from a sulfite waste liquor, and 7 parts by weight of powdered silica gel. By finely dispersing the mixture in water, a spray liquor is obtained.
VI. An intimate mixture of 3 parts by weight of compound no. 6 from Table 3 and 97 parts by weight of particulate kaolin. The dust contains 3wt% of the active ingredient.
VII. An intimate mixture of 30 parts by weight of compound no. 7 from Table 3, 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil sprayed onto the surface of this silica gel. This formulation of the active ingredient exhibits good adherence.
VIII. A stable aqueous dispersion of 40 parts by weight of compound no. 8 from Table 3, 10 parts of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts of silica gel and 43 parts of water, which dispersion can be further diluted.
IX. A stable oily dispersion of 20 parts by weight of compound no. 9 from Table 3, 2 parts by weight of the calcium salt of dodecylben~enesulfonic acid, 8 parts by BASF Aktiengeeellachaft 920400 O.Z. 0050/43411 81 2100~4~

weight of a fatty alcohol polyglycol ether, 2 parts by weight of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 par~s by weight of a paraf-finic mineral oil.

The novel compounds are extremely effective on a broad spectrum of phytopathogenic fungi, in particular those from the class consisting of the Ascomycetes and Basidiomycetes.
Some of them have a systemic action and can be used as foliar and soil fungicides.
The fungicidal compounds are of particular interest for controlling a large number of fungi in various crops or their seeds, especially wheat, rye, barley, oats, rice, Indian corn, lawns, cotton, soybeans, coffee, sugar cane, fruit and ornamentals in horticulture and viticulture, and in vegetables such as cucumbers, beans and cucurbits.
The compounds are applied by treating the fungi or the seeds, plants, materials or the soil to be protected against fungus attack with an effective amount of the active ingre-dients.
Application may be effected before or after infection of the 2S materials, plants or seed by the fungi.
The compounds I are particularly useful for controlling the following plant diseases:
Erysiphe graminis in cereals, Erysiphe cichoracearum and Sphaerotheca fuliginea in cucur-bits, Podosphaera leucotricha in apples, Uncinula necator in vines, Puccinia species in cereals, Rhizoctonia solani in cotton, Ustilago species in cereals and sugar cane, Venturia inaequalis (scab) in apples, Helminthosporium species in cereals, Septoria nodorum in wheat, Botrytis cinerea (gray mold) in strawberries and grapes, Cercospora arachidicola in groundnuts, Pseudocercosporella herpotrichoides in wheat and barle B~SF Aktiengeaell~chaft 920400 O.Z. 0050/43411 .
82 210~4S

Pyricularia oryzae in rice, Phytophthora infestans in potatoes and tomatoes, Fusarium and Verticillium species in various plants, Plasmopara viticola in grapes, Alternaria species in fruit and vegetables.
The novel compounds may also be used for protecting materi-als (timber) against, for example, Paecilomyces variotii.
Generally, the fungicidal agents contain from 0.1 to 95, and preferably from 0.5 to 90, wt~ of active ingredient.
The application rates depend on the effect desired, and vary from 0.02 to 3 kg of active ingredient per hectare.
When the active ingredients are used for treating seed, ra-tes of from 0.001 to 50, and preferably from 0.01 to 10, g per kg of seed are generally needed.
When applied as fungicides, the agents according to the in-vention may also be present together with other active in-gredients, for example herbicides, insecticides, growth re-gulators, other fungicides, or fertilizers.
When admixed with other fungicides, the fungicidal spectrum of action is in many cases increased.
Use examples The active ingredient used for comparison purposes was me-thyl 2-(2-hydroxyphenyl)-3-methoxyacrylate (A) disclosed in EP 251 082.
Use Example 1 Action on Plasmopara viticola Leaves of potted vines of the Muller-Thurgau variety were sprayed with aqueous suspensions containing (dry basis) 80%
of active ingredient and 20% of emulsifier. To assess the duration of action, the plants were set up, after the sprayed-on layer had dried, for 8 days in the greenhouse.
Then the leaves were infected with a zoospore suspension of BASF Aktienge~ chaft 920400 O.Z. 0050/43411 83 210~4~

Plasmopara viticola. The plants were first placed for 48 hours in a water vapor-saturated chamber at 24C and then in a greenhouse for 5 days at from 20 to 30"C. To accelerate and intensify the sporangiophore discharge, the plants were then again placed in the moist chamber for 16 hours. The extent of fungus attack was then assessed on the undersides of the leaves.
The results show that active ingredients nos. 3, 4, 5, 6, 7, 8, lO, 11, 12, 13, 1~, 18, 26, 28 und 29 from Table 3, when applied as spray liquors containing 250 ppm (by weight) of active ingredient, have a better fungicidal action (90%) than prior art comparative agent A (40%).
Use example 2 Action on wheat brown rust Leaves of pot-grown wheat seedlings of the ~Kanzler~ variety were dusted with spores of brown rust (Puccinia recondita).
The pots were then placed for 24 hours at 20 to 22C in a high-humidity (90 - 95%) chamber. During this period the spores germinated and the germ tubes penetrated the leaf tissue. The infected plants were then sprayed to runoff with aqueous liquors containing (dry basis) 80% of active ingre-dient and 20~ of emulsifier. After the sprayed-on layer had dried, the plants were set up in the greenhouse at 20 to 22~C and a relative humidity of 65 to 70%. The extent of rust fungus spread on the leaves was assessed after 8 days.
The results of the experiment show that active ingredients nos. 7, 8, 10 and 31 from Table 3, when applied as a spray liquor containing 250 ppm of active ingredient, have a bet-ter fungicidal action (95~) than prior art comparative com-pound A (0%).

Claims (11)

1. A substituted acrylate of the formula I

where B is alkyl which is substituted by 1-4 identical or different substituents R3, alkenyl which is substituted by 1-4 identical or different substituents R4, alkynyl which is substituted by 1-4 identical or different substituents R5, cycloalkyl which is substituted by 1-4 identical or different substituents R6, cycloalkenyl which is substituted by 1-4 identical or different substituents R7, cycloalkynyl which is substituted by 1-4 identical or different substituentc R8 or heterocyclyl which is substituted by 1-4 identical or different substituents R9, X and Y independently of one another are each hydrogen, halogen, cyano, nitro, haloalkyl, alkyl, haloalkoxy, alkenyl, alkynyl, cycloalkyl, aryl, hetaryl, heterocycl-yl, cycloalkenyl, cycloalkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, aryloxy, hetaryloxy, hetero-cyclyloxy, cycloalkenyloxy, cycloalkynyloxy, alkoximino, alkenyloximino, alkynyloximino, cycloalkyloximino, cycloalkenyloximino, cycloalkynyloximino, aryloximino, hetaryloximino, heterocycyloximino, alkoxycarbonyl, alkonyloxycarbonyl, alkynyloxycarbonyl, cycloalkyloxy-carbonyl aryloxycarbonyl, hetaryloxycarbonyl, hetero-cyclyloxycarbonyl,cycloalkenyloxycarbonyl,cycloalkynyl-oxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkenylaminocarbonyl, dialkenylaminocarbonyl, alkynyl-aminocarbonyl, dialkynylaminocarbonyl, cycloalkylamino-carbonyl, cycloalkenylaminocarbonyl, cycloalkynylamino-- 85 - O.Z. 0050/43411 carbonyl, arylaminocarbonyl, hetarylaminocarbonyl, heterocyclylaminocarbonyl, alkylthio, alkenylthio, alkynylthio, cycloalkylthio, arylthio, hetarylthio, heterocyclylthio, cycloalkenylthio, cycloalkynylthio, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, arylamino, hetarylamino, heterocyclylamino, cycloalkenyl-amino, cycloalkynylamino, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, het-arylcarbonyl,heterocyclylcarbonyl,cycloalkenylcarbonyl, cycloalkynylcarbonyl, alkylsulfoxyl, alkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl, arylsulfoxyl, hetarylsulfoxyl, heterocyclylsulfoxyl, cycloalkynyl-sulfoxyl, cycloalkenylsulfoxyl, alkylsulfonyl, alkenyl-sulfonyl, alkynylsulfonyl, cycloalkylsulfonyl, aryl-sulfonyl, hetarylsulfonyl, heterocyclylsulfonyl, cyclo-alkenylsulfonyl, cycloalkynylsulfonyl, alkylsulfinyl, alkenylsulfinyl, alkynylsulfinyl, cycloalkylsulfinyl, arylsulfinyl, hetarylsulfinyl, heterocyclylsulfinyl, cycloalkenylsulfinyl, cycloalkynylsulfinyl, alkyl-carbonyloxy, alkenylcarbonyloxy, alkynylcarbonyloxy, cycloalkylcarbonyloxy, cycloalkenylcarbonyloxy, cyclo-alkynylcarbonyloxy, arylcarbonyloxy, hetarylcarbonyloxy, heterocyclylcarbonyloxy, alkylcarbonylamino, alkenyl-carbonylamino, alkynylcarbonylamino, cycloalkylcarbonyl-amino, cycloalkenylcarbonylamino, cycloalkynylcarbonyl-amino, arylcarbonylamino, hetarylcarbonylamino, hetero-cyclylcarbonylamino, cycloalkylalkoxy, cycloalkenyl-alkoxy, cylcoalkynylalkoxy, arylalkoxy, hetarylalkoxy or heterocyclylalkoxy, if X and Y are on adjacent carbon atoms, they may be condensed to form an unsubstituted or substituted aroma-tic or heteroaromatic, alicyclic or heterocyclic, par-tially or completely hydrogenated ring, R1 and R2 may be substituted and independently of one another are each alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl, R3 and R4 may be substituted by 1-4 identi-cal or different substituents R10, and R3 and R4 are each - 86 - O.Z. 0050/43411 nitro, haloalkoxy, alkoxy, alkynyl, cycloalkyl, hetaryl, heterocyclyl, cycloalkenyl, cycoalkynyl, alkenyloxy, alkynyloxy, cycloalkoxy, hetaryloxy, heterocyclyloxy, cycloalkenyloxy, cycloalkynyloxy, alkoximino, alkenyl-oximino, alkynyloximino, cycloalkyloximino, cycloalkenyl-oximino, cycloalkynyloximino, aryloximino, hetarylox-imino, heterocyclyloximino, cycloalkyloxycarbonyl aryloxycarbonyl, hetaryloxycarbonyl, heterocyclyloxy-carbonyl, cycloalkenyloxycarbonyl, cycloalkynyloxy-carbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkenylaminocarbonyl, dialkenylaminocarbonyl, alkynyl-aminocarbonyl, dialkynylaminocarbonyl, cycloalkylamino-carbonyl, cycloalkenylaminocarbonyl, cycloalkynylamino-carbonyl, arylaminocarbonyl, hetarylaminocarbonyl, heterocyclylaminocarbonyl, alkylthio, alkenylthio, alkynylthio, cycloalkylthio, arylthio, hetarylthio, heterocyclylthio, cycloalkenylthio, cycloalkynylthio, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, arylamino, hetarylamino, heterocyclylamino, cycloalkenyl-amino, cycloalkynylamino, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, het-arylcarbonyl,heterocyclylcarbonyl,cycloalkenylcarbonyl, cycloalkynylcarbonyl, alkylsulfoxyl, alkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl, arylsulfoxyl, hetarylsulfoxyl, heterocyclylsulfoxyl, cycloalkynyl-sulfoxyl, cycloalkenylsulfoxyl, alkylsulfonyl, alkenyl-sulfonyl, alkynylsulfonyl, cycloalkylsulfonyl, aryl-sulfonyl, hetarylsulfonyl, heterocyclylsulfonyl, cyclo-alkenylsulfonyl, cycloalkynylsulfonyl, alkylsulfinyl, alkenylsulfinyl, alkynylsulfinyl, cycloalkylsulfinyl, arylsulfinyl, hetarylsulfinyl, heterocyclylsulfinyl, cycloalkenylsulfinyl, cycloalkynylsulfinyl, alkyl-carbonyloxy, alkenylcarbonyloxy, alkynylcarbonyloxy, cycloalkylcarbonyloxy, cycloalkenylcarbonyloxy, cyclo-alkynylcarbonyloxy, arylcarbonyloxy, hetarylcarbonyloxy, heterocyclylcarbonyloxy, alkylcarbonylamino, alkenyl-carbonylamino, alkynylcarbonylamino, cycloalkylcarbonyl-- 87 - O.Z. 0050/43411 amino, cycloalkenylcarbonylamino, cycloalkynylcarbonyl-amino, arylcarbonylamino, hetarylcarbonylamino, hetero-cyclylcarbonylamino, cycloalkylalkoxy, cycloalkenyl-alkoxy, cycloalkynylalkoxy, hetarylalkoxy, heterocyclyl-alkoxy, alkynylalkenyl, cycloalkylalkenyl, cycloalkenylalkenyl,cycloalkynylalkenyl,hetarylalkenyl, heterocyclylalkenyl, alkoximinoalkyl, alkenyloximinoalkyl, alkynyloximinoalkyl, cycloalkox-iminoalkyl, cycloalkenyloximinoalkyl, cycloalkynylox-iminoalkyl, aryloximinoalkyl, hetaryloximinoalkyl, heterocyclyloximinoalkyl, alkoximinoalkenyl, alkenylox-iminoalkenyl, alkynyloximinoalkenyl, cycloalkoximino-alkenyl,cycloalkenyloximinoalkenyl,cycloalkynyloximino-alkenyl, aryloximinoalkenyl, hetaryloximinoalkenyl or heterocyclyloximinoalkenyl, R5, R6, R7 and R8 may be substituted by 1-4 identical or different substituents R10, and R5, R6, R7 and R8 are each nitro, haloalkyl, alkyl, haloalkoxy, alkenyl, alkynyl, cycloalkyl, aryl, hetaryl, heterocyclyl, cycloalkenyl, cycloalkynyl, alkoxy, alkenyloxy, alkynyloxy, cyclo-alkoxy, aryloxy, hetaryloxy, heterocyclyloxy, cyclo-alkenyloxyl, cycloalkynyloxy, alkoximino, alkenyloximino, alkynyloximino, cycloalkyloximino, cycloalkenyloximino, cycloalkynyloximino, aryloximino, hetaryloximino, hetero-cyclyloximino, cycloalkoxycarbonyl, aryloxycarbonyl, het-aryloxycarbonyl, heterocyclyloxycarbonyl, cycloalkenyloxycarbonyl, cycloalkynyloxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkenylaminocarbonyl, dialkenylaminocarbonyl, alkynylaminocarbonyl, dialkynylaminocarbonyl, cycloalkylaminocarbonyl, cycloalkenylaminocarbonyl, cycloalkynylaminocarbonyl, arylaminocarbonyl, hetarylaminocarbonyl, heterocyclylaminocarbonyl, alkyl-thio, alkenylthio, alkynylthio, cycloalkylthio, arylthio, hetarylthio, heterocyclylthio, cycloalkenylthio, cyclo-alkynylthio, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, arylamino, hetarylamino, heterocyclyl-- 88 - O.Z. 0050/43411 amino, cycloalkenylamino, cycloalkynylamino, alkylcarbon-yl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, hetarylcarbonyl, heterocyclylcarbonyl, cycloalkenylcarbonyl, cycloalkynylcarbonyl, alkylsulfox-yl, alkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl, arylsulfoxyl, hetarylsulfoxyl, heterocyclylsulfoxyl, cycloalkynylsulfoxyl, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, hetarylsulfonyl, heterocyclylsulfonyl, cycloalkenyl-sulfonyl, cycloalkynylsulfonyl, alkylsulfinyl, alkenyl-sulfinyl, alkynylsulfinyl, cycloalkylsulfinyl, aryl-sulfinyl, hetarylsulfinyl, heterocyclylsulfinyl, cyclo-alkenylsulfinyl, cycloalkynylsulfinyl, alkylcarbonyloxy, alkenylcarbonyloxy,alkynylcarbonyloxy,cycloalkylcarbon-yloxy, cycloalkenylcarbonyloxy, cycloalkynylcarbonyloxy, arylcarbonyloxy, hetarylcarbonyloxy, heterocyclylcarbon-yloxy, alkylcarbonylamino, alkenylcarbonylamino, alkynyl-carbonylamino, cycloalkylcarbonylamino, cycloalkenyl-carbonylamino, cycloalkynylcarbonylamino, arylcarbonyl-amino, hetarylcarbonylamino or heterocyclylcarbonylamino, R9 may be substituted by 1-4 identical or different substituents R10, and R9 is hydrogen, halogen, cyano, nitro, haloalkyl, alkyl, haloalkoxy, alkenyl, alkynyl, cycloalkyl, aryl, hetaryl, heterocyclyl, cycloalkenyl, cycloalkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalk-oxy, aryloxy, hetaryloxy, heterocyclyloxy, cycloalkenyl-oxy, cycloalkynyloxy, alkoximino, alkenyloximino, alkynyloximino,cycloalkyloximino,cyclocoalkenyloximino, cycloalkynyloximino, aryloximino, hetaryloximino, hetero-cyclyloximino, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl,cycloalkoxycarbonyl,aryloxycarbonyl, hetaryloxycarbonyl, heterocyclyoxycarbonyl, cycloalkenyloxycarbonyl, cycloalkynyloxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkenylaminocarbonyl, dialkenylaminocarbonyl, alkynylaminocarbonyl, dialkynylaminocarbonyl, cycloalkylaminocarbonyl, cycloalkenylaminocarbonyl, - 89 - O.Z. 0050/43411 cycloalkynylaminocarbonyl, arylaminocarbonyl, hetarylaminocarbonyl, heterocyclylaminocarbonyl, alkyl-thio, alkenylthio, alkynylthio, cycloalkylthio, arylthio, hetarylthio, heterocyclylthio, cycloalkenylthio, cyclo-alkynylthio, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, arylamino, hetarylamino, heterocyclyl-amino, cycloalkenylamino, cycloalkynylamino, alkylcarbon-yl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, hetarylcarbonyl, heterocyclylcarbonyl, cycloalkenylcarbonyl, cycloalkynylcarbonyl, alkylsulfox-yl, alkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl, arylsulfoxyl, hetarylsulfoxyl, heterocyclylsulfoxyl, cycloalkynylsulfoxyl, cycloalkenylsulfoxyl, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, hetarylsulfonyl, heterocyclylsulfonyl, cycloalkenylsulfonyl, cycloalkynylsulfonyl, alkylsulfinyl, alkenylsulfinyl, alkynylsulfinyl, cycloalkylsulfinyl, arylsulfinyl, hetarylsulfinyl, heterocyclylsulfinyl, cycloalkenyl-sulfinyl, cycloalkynylsulfinyl, alkylcarbonyloxy, alkenylcarbonyloxy,alkynylcarbonyloxy,cycloalkylcarbon-yloxy, cycloalkenylcarbonyloxy, cycloalkynylcarbonyloxy, arylcarbonyloxy, hetarylcarbonyloxy, heterocyclylcarbon-yloxy, alkylcarbonylamino, alkenylcarbonylamino, alkynyl-carbonylamino, cycloalkylcarbonylamino, cycloalkenyl-carbonylamino, cycloalkynylcarbonylamino, arylcarbonyl-amino, hetarylcarbonylamino, heterocyclylcarbonylamino, cycloalkylalkoxy,cycloalkenylalkoxy,cycloalkynylalkoxy, arylalkoxy, hetarylalkoxy or heterocyclylalkoxy, R10 may be substituted by 1-4 identical or different substituents R11, and R10 is hydrogen, halogen, cyano, nitro, haloalkyl, alkyl, haloalkoxy, alkenyl, alkynyl, cycloalkyl, aryl, hetaryl, heterocyclyl, cycloalkenyl, cycloalkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalk-oxy, aryloxy, hetaryloxy, heterocyclyloxy, cycloalkenyl-oxy, cycloalkynyloxy, alkoximino, alkenyloximino, alkynyloximino, cycloalkyloximino, cycloalkenyloximino, - 90 - O.Z. 0050/43411 cycloalkynyloximino, aryloximino, hetaryloximino, hetero-cyclyloximino, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl,cycloalkoxycarbonyl,aryloxycarbonyl, hetaryloxycarbonyl, heterocyclyloxycarbonyl, cyclo-alkenyloxycarbonyl, cycloalkynyloxycarbonyl, alkyl-aminocarbonyl, dialkylaminocarbonyl, alkenylamino-carbonyl, dialkenylaminocarbonyl, alkynylaminocarbonyl, dialkynylaminocarbonyl, cycloalkylaminocarbonyl, cyclo-alkenylaminocarbonyl, cycloalkynylaminocarbonyl, arylaminocarbonyl, hetarylaminocarbonyl, heterocyclylaminocarbonyl, alkylthio, alkenylthio, alkynylthio, cycloalkylthio, arylthio, hetarylthio, heterocyclylthio, cycloalkenylthio, cycloalkynylthio, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, arylamino, hetarylamino, heterocyclylamino, cycloalkenylamino, cycloalkynylamino, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, hetarylcarbonyl, heterocyclylcarbonyl, cycloalkenylcarbonyl, cycloalkynylcarbonyl, alkylsulfox-yl, alkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl, arylsulfoxyl, hetarylsulfoxyl, heterocyclylsulfoxyl, cycloalkynylsulfoxyl, cycloalkenylsulfoxyl, alkyl-sulfonyl, alkenylsulfonyl, alkynylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, hetarylsulfonyl, heterocyclylsulfonyl, cycloalkenylsulfonyl, cylcoalkynylsulfonyl, alkylsulfinyl, alkenylsulfinyl, alkynylsulfinyl, cycloalkylsulfinyl, arylsulfinyl, hetarylsulfinyl, heterocyclylsulfinyl, cycloalkenyl-sulfinyl, cycloalkynylsulfinyl, alkylcarbonyloxy, alkenylcarbonyloxy,alkynylcarbonyloxy,cycloalkylcarbon-yloxy, cycloalkenylcarbonyloxy, cycloalkynylcarbonyloxy, arylcarbonyloxy, hetarylcarbonyloxy, heterocyclylcarbon-yloxy, alkylcarbonylamino, alkenylcarbonylamino, alkynyl-carbonylamino, cycloalkylcarbonylamino, cycloalkenyl-carbonylamino, cycloalkynylcarbonylamino, arylcarbonyl-amino, hetarylcarbonylamino, heterocyclylcarbonylamino, cycloalkylalkoxy,cycloalkenylalkoxy,cycloalkynylalkoxy, - 91 - O.Z. 0050/43411 arylalkoxy, hetarylalkoxy or heterocyclylalkoxy, R11 may be substituted and is hydrogen, cyano, nitro, haloalkyl, alkyl, haloalkoxy, alkenyl, alkynyl, cyclo-alkyl, aryl, hetaryl, heterocyclyl, cylcoalkenyl, cyclo-alkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, aryloxy, hetaryloxy, heterocyclyloxy, cycloalkenyloxy, cycloalkynyloxy, alkoximino, alkenyloximino, alkynyl-oximino, cycloalkyloximino, cyclocoalkenyloximino, cycloalkynyloximino, aryloximino, hetaryloximino, hetero-cyclyloximino, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl,cycloalkoxycarbonyl,aryloxycarbonyl, hetaryloxycarbonyl, heterocyclyloxycarbonyl, cycloalkenyloxycarbonyl, cycloalkynyloxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkenylaminocarbonyl, dialkenylaminocarbonyl, alkynylaminocarbonyl, dialkynylaminocarbonyl, cycloalkylaminocarbonyl, cycloalkenylaminocarbonyl, cycloalkynylaminocarbonyl, arylaminocarbonyl, hetarylaminocarbonyl, heterocyclylaminocarbonyl, alkyl-thio, alkenylthio, alkynylthio, cycloalkylthio, arylthio, hetarylthio, heterocyclylthio, cycloalkenylthio, cyclo-alkynylthio, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, arylamino, hetarylamino, heterocyclyl-amino, cycloalkenylamino, cycloalkynylamino, alkylcarbon-yl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, hetarylcarbonyl, heterocyclylcarbonyl, cycloalkenylcarbonyl, cycloalkynylcarbonyl, alkylsulfox-yl, alkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl, arylsulfoxyl, hetarylsulfoxyl, heterocyclylsulfoxyl, cycloalkynylsulfoxyl, cycloalkenylsulfoxyl, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, hetarylfiulfonyl, heterocyclylsulfonyl, cycloalkenylsulfonyl, cycloalkynylsulfonyl, alkylsulfinyl, alkenylsulfinyl, alkynylsulfinyl, cycloalkylsulfinyl, arylsulfinyl, hetarylsulfinyl, heterocyclylsulfinyl, cycloalkenyl-sulfinyl, cycloalkynylsulfinyl, alkylcarbonyloxy, - 92 - O.Z. 0050/43411 alkenylcarbonyloxy,alkynylcarbonyloxy,cycloalkylcarbon-yloxy, cycloalkenylcarbonyloxy, cycloalkynylcarbonyloxy, arylcarbonyloxy, hetarylcarbonyloxy, heterocyclylcarbon-yloxy, alkylcarbonylamino, alkenylcarbonylamino, alkynyl-carbonylamino, cycloalkylcarbonylamino, cycloalkenyl-carbonylamino, cycloalkynylcarbonylamino, arylcarbonyl-amino, hetarylcarbonylamino, heterocyclylcarbonylamino, cycloalkylalkoxy,cycloalkenylalkoxy,cycloalkynylalkoxy, arylalkoxy, hetarylalkoxy or heterocyclylalkoxy, and the acid addition products and base addition products of this compound.
2. A substituted acrylate of the formula II

II

where R1, R2, R3, X and Y have the meanings stated in claim 1 and m is 1, 2, 3 or 4.
3. A substituted acrylate of the formula III
III

where R1, R2, R4, X and Y have the meanings stated in claLm 1 and m is 1, 2, 3 or 4.
4. A substituted acrylate of the formula IV

- 93 - O.Z. 0050/43411 IV

where R1, R2, R5, X and Y have the meanings stated in claim 1 and m is 1, 2, 3 or 4.
5. A substituted acrylate of the formula V
V

where R1, R2, R6, X and Y have the meanings stated in claim 1 and m is 1, 2, 3 or 4.
6. A substituted acrylate of the formula VI
VI

where R1, R2, R7, X and Y have the meanings stated in claim 1 and m is 1, 2, 3 or 4.
7. A substituted acrylate of the formula VII

VII

- 94 - O.Z. 0050/43411 where R1, R2, R8, X and Y have the meanings stated in claim 1 and m is 1, 2, 3 or 4.
8. A substituted acrylate of the formula VIII

VIII

where R1, R2, R9, X and Y have the meanings stated in claim 1 and m is 1, 2, 3 or 4.
9. A compound of the formula IX

IX

where R1, R2, X and Y have the meanings stated in claim 1.

- 95 - O.Z. 0050/43411
10. A fungicide containing an inert carrier and a fungicidal amount of a substituted acrylate of the formula I
I

where B is alkyl which is substituted by 1-4 identical or different substituents R3, alkenyl which is substituted by 1-4 identical or different substituents R4, alkynyl which is substituted by 1-4 identicsl or different substituents R5, cycloalkyl which is substituted by 1-4 identical or different substituents R6, cycloalkenyl which is substituted by 1-4 identical or different substituents R7, cycloalkynyl which is substituted by 1-4 identical or different substituents R8 or heterocyclyl which is substituted by 1-4 identical or different substituents R9, X and Y independently of one another are each hydrogen, halogen, cyano, nitro, haloalkyl, alkyl, haloalkoxy, alkenyl, alkynyl, cycloalkyl, aryl, hetaryl, heterocycl-yl, cycloalkenyl, cycloalkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, aryloxy, hetaryloxy, hetero-cyclyloxy, cycloalkenyloxy, cycloalkynyloxy, alkoximino, alkenyloximino, alkynyloximino, cycloalkyloximino, cycloalkenyloximino, cycloalkynyloximino, aryloximino, hetaryloximino, heterocyclyloximino, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, cycloalkyloxy-- 96 - O.Z. 0050/43411 carbonyl aryloxycarbonyl, hetaryloxycarbonyl, hetero-cyclyloxycarbonyl,cycloalkenyloxycarbonyl,cycloalkynyl-oxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkenylaminocarbonyl, dialkenylaminocarbonyl, alkynyl-aminocarbonyl, dialkynylaminocarbonyl, cycloalkylamino-carbonyl, cycloalkenylaminocarbonyl, cycloalkynylamino-carbonyl, arylaminocarbonyl, hetarylaminocarbonyl, heterocyclylaminocarbonyl, alkylthio, alkenylthio, alkynylthio, cycloalkylthio, arylthio, hetarylthio, heterocyclylthio, cycloalkenylthio, cycloalkynylthio, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, arylamino, hetarylamino, heterocyclylamino, cycloalkenyl-amino, cycloalkynylamino, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, het-arylcarbonyl,heterocyclylcarbonyl,cycloalkenylcarbonyl, cycloalkynylcarbonyl, alkylsulfoxyl, alkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl, arylsulfoxyl, hetarylsulfoxyl, heterocyclylsulfoxyl, cycloalkynyl-sulfoxyl, cycloalkenylsulfoxyl, alkylsulfonyl, alkenyl-sulfonyl, alkynylsulfonyl, cycloalkylsulfonyl, aryl-sulfonyl, hetarylsulfonyl, heterocyclylsulfonyl, cyclo-alkenylsulfonyl, cycloalkynylsulfonyl, alkyl sulfinyl, alkenylsulfinyl, alkynylsulfinyl, cycloalkylsulfinyl, arylsulfinyl, hetarylsulfinyl, heterocyclylsulfinyl, cycloalkenylsulfinyl, cycloalkynylsulfinyl, alkyl-carbonyloxy, alkenylcarbonyloxy, alkynylcarbonyloxy, cycloalkylcaxbonyloxy, cycloalkenylcarbonyloxy, cyclo-alkynylcarbonyloxy, arylcarbonyloxy, hetarylcarbonyloxy, heterocyclylcarbonyloxy, alkylcarbonylamino, alkenyl-carbonylamino, alkynylcarbonylamino, cycloalkylcarbonyl-amino, cycloalkenylcarbonylamino, cycloalkynylcarbonyl-amino, arylcarbonylamino, hetarylcarbonylamino, hetero-cyclylcarbonylamino, cycloalkylalkoxy, cycloalkenyl-alkoxy, cylcoalkynylalkoxy, arylalkoxy, hetarylalkoxy or heterocyclylalkoxy, if X and Y are on adjacent carbon atoms, they may be condensed to form an unsubstituted or substituted - 97 - O.Z. 0050/43411 aromatic or heteroaromatic, alicyclic or heterocyclic, partially or completely hydrogenated ring, R1 and R2 may be substituted and independently of one another are each alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl, R3 and R4 may be substituted by 1-4 identi-cal or different substituents R10, and R3 and R4 are each nitro, haloalkoxy, alkoxy, alkynyl, cycloalkyl, hetaryl, heterocyclyl, cycloalkenyl, cycloalkynyl, alkenyloxy, alkynyloxy, cycloalkoxy, hetaryloxy, heterocyclyloxy, cycloalkenyloxy, cycloalkynyloxy, alkoximino, alkenyl-oximino, alkynyloximino, cycloalkyloximino, cycloalkenyl-oximino, cycloalkynyloximino, aryloximino, hetarylox-imino, heterocyclyloximino, cycloalkoxycarbonyl aryloxycarbonyl, hetaryloxycarbonyl, heterocyclyloxy-carbonyl, cycloalkenyloxycarbonyl, cycloalkynyloxy-carbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkenylaminocarbonyl, dialkenylaminocarbonyl, alkynyl-aminocarbonyl, dialkynylaminocarbonyl, cycloalkylamino-carbonyl, cycloalkenylaminocarbonyl, cycloalkynylamino-carbonyl, arylaminocarbonyl, hetarylaminocarbonyl, heterocyclylaminocarbonyl, alkylthio, alkenylthio, alkynylthio, cycloalkylthio, arylthio, hetarylthio, heterocyclylthio, cycloalkenylthio, cycloalkynylthio, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, arylamino, hetarylamino, heterocyclylamino, cycloalkenyl-amino, cycloalkynylamino, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, het-arylcarbonyl,heterocyclylcarbonyl,cycloalkenylcarbonyl, cycloalkynylcarbonyl, alkylsulfoxyl, alkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl, arylsulfoxyl, hetarylsulfoxyl, heterocyclylsulfoxyl, cycloalkynyl-sulfoxyl, cycloalkenylsulfoxyl, alkylsulfonyl, alkenyl-sulfonyl, alkynylsulfonyl, cycloalkylsulfonyl, aryl-sulfonyl, hetarylsulfonyl, heterocyclylsulfonyl, cyclo-alkenylsulfonyl, cylcoalkynylsulfonyl, alkylsulfinyl, alkenylsulfinyl, alkynylsulfinyl, cycloalkylsulfinyl, arylsulfinyl, hetarylsulfinyl, heterocyclylsulfinyl, - 98 - O.Z. 0050/43411 cycloalkenylsulfinyl, cycloalkynylsulfinyl, alkyl-carbonyloxy, alkenylcarbonyloxy, alkynylcarbonyloxy, cycloalkylcarbonyloxy, cycloalkenylcarbonyloxy, cyclo-alkynylcarbonyloxy, arylcarbonyloxy, hetarylcarbonyloxy, heterocyclylcarbonyloxy, alkylcarbonylamino, alkenyl-carbonylamino, alkynylcarbonylamino, cycloalkylcarbonyl-amino, cycloalkenylcarbonylamino, cycloalkynylcarbonyl-amino, arylcarbonylamino, hetarylcarbonylamino, hetero-cyclylcarbonylamino, cycloalkylalkoxy, cycloalkenyl-alkoxy, cycloalkynylalkoxy, hetarylalkoxy, heterocyclyl-alkoxy, alkynylalkenyl, cycloalkylalkenyl, cycloalkenylalkenyl, cycloalkynylalkenyl, hetarylalkenyl, h e t e r o c y c l y l a l k e n y l, a l k o x i m i n o a l k y l, alkenyloximinoalkyl, alkynyloximinoalkyl, cycloalkox-iminoalkyl, cycloalkenyloximinoalkyl, cycloalkynylox-iminoalkyl, aryloximinoalkyl, hetaryloximinoalkyl, heterocyclyloximinoalkyl, alkoximinoalkenyl, alkenylox-iminoalkenyl, alkynyloximinoalkenyl, cycloalkoximino-alkenyl, cycloalkenyloximinoalkenyl, cycloalkynyloximino-alkenyl, aryloximinoalkenyl, hetaryloximinoalkenyl or heterocyclyloximinoalkenyl, R5, R6, R7 and R8 may be substituted by 1-4 identical or different substituents R10, and R5, R6, R7 and R8 are each nitro, haloalkyl, alkyl, haloalkoxy, alkenyl, alkynyl, cycloalkyl, aryl, hetaryl, heterocyclyl, cycloalkenyl, cycloalkynyl, alkoxy, alkenyloxy, alkynyloxy, cyclo-alkoxy, aryloxy, hetaryloxy, heterocyclyloxy, cyclo-alkenyloxyl, cycloalkynyloxy, alkoximino, alkenyloximino, alkynyloximino, cycloalkyloximino, cycloalkenyloximino, cycloalkynyloximino, aryloximino, hetaryloximino, hetero-cyclyloximino, cycloalkoxycarbonyl, aryloxycarbonyl, het-aryloxycarbonyl, heterocyclyoxycarbonyl, cycloalkenyloxy-carbonyl, cycloalkynyloxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkenylaminocarbonyl, dialkenyl-aminocarbonyl, alkynylaminocarbonyl, dialkynylamino-carbonyl, cycloalkylaminocarbonyl, cycloalkenylamino-carbonyl, cycloalkynylaminocarbonyl, arylaminocarbonyl, - 99 - O.Z. 0050/43411 hetarylaminocarbonyl, heterocyclylaminocarbonyl, alkyl-thio, alkenylthio, alkynylthio, cycloalkylthio, arylthio, hetarylthio, heterocyclylthio, cycloalkenylthio, cyclo-alkynylthio, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, arylamino, hetarylamino, heterocyclyl-amino, cycloalkenylamino, cycloalkynylamino, alkylcarbon-yl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, hetarylcarbonyl, heterocyclylcarbonyl, cycloalkenylcarbonyl, cycloalkynylcarbonyl, alkylsulfox-yl, alkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl, arylsulfoxyl, hetarylsulfoxyl, heterocyclylsulfoxyl, cycloalkynylsulfoxyl, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, hetarylsulfonyl, heterocyclylsulfonyl, cycloalkenyl-sulfonyl, cycloalkynylsulfonyl, alkylsulfinyl, alkenyl-sulfinyl, alkynylsulfinyl, cycloalkylsulfinyl, aryl-sulfinyl, hetarylsulfinyl, heterocyclylsulfinyl, cyclo-alkenylsulfinyl, cycloalkynylsulfinyl, alkylcarbonyloxy, alkenylcarbonyloxy,alkynylcarbonyloxy,cycloalkylcarbon-yloxy, cycloalkenylcarbonyloxy, cycloalkynylcarbonyloxy, arylcarbonyloxy, hetarylcarbonyloxy, heterocyclylcarbon-yloxy, alkylcarbonylamino, alkenylcarbonylamino, alkynyl-carbonylamino, cycloalkylcarbonylamino, cycloalkenyl-carbonylamino, cycloalkynylcarbonylamino, arylcarbonyl-amino, hetarylcarbonylamino or heterocyclylcarbonylamino, R9 may be substituted by 1-4 identical or different substituents R10, and R9 is hydrogen, halogen, cyano, nitro, haloalkyl, alkyl, haloalkoxy, alkenyl, alkynyl, cycloalkyl, aryl, hetaryl, heterocyclyl, cycloalkenyl, cycloalkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalk-oxy, aryloxy, hetaryloxy, heterocyclyloxy, cycloalkenyl-oxy, cycloalkynyloxy, alkoximino, alkenyloximino, alkynyloximino, cycloalkoximino, cyclocoalkenyloximino, cycloalkynyloximino, aryloximino, hetaryloximino, hetero-cyclyloximino, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl,cycloalkoxycarbonyl,aryloxycarbonyl, hetaryloxycarbonyl, heterocyclyoxycarbonyl, - 100 - O.Z. 0050/43411 cycloalkenyloxycarbonyl, cycloalkynyloxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkenylaminocarbonyl, dialkenylaminocarbonyl, alkynylaminocarbonyl, dialkynylaminocarbonyl, cycloalkylaminocarbonyl, cycloalkenylaminocarbonyl, cycloalkynylaminocarbonyl, arylaminocarbonyl, hetarylaminocarbonyl, heterocyclylaminocarbonyl, alkyl-thio, alkenylthio, alkynylthio, cycloalkylthio, arylthio, hetarylthio, heterocyclylthio, cycloalkenylthio, cyclo-alkynylthio, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, arylamino, hetarylamino, heterocyclyl-amino, cycloalkenylamino, cycloalkynylamino, alkylcarbon-yl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, hetarylcarbonyl, heterocyclylcarbonyl, cycloalkenylcarbonyl, cycloalkynylcarbonyl, alkylsulfox-yl, alkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl, arylsulfoxyl, hetarylsulfoxyl, heterocyclylsulfoxyl, cycloalkynylsulfoxyl, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, hetarylsulfonyl, heterocyclylsulfonyl, cycloalkenyl-sulfonyl, cycloalkynylsulfonyl, alkylsulfinyl, alkenyl-sulfinyl, alkynylsulfinyl, cycloalkylsulfinyl, aryl-sulfinyl, hetarylsulfinyl, heterocyclylsulfinyl, cyclo-alkenylsulfinyl, cycloalkynylsulfinyl, alkylcarbonyloxy, alkenylcarbonyloxy,alkynylcarbonyloxy,cycloalkylcarbon-yloxy, cycloalkenylcarbonyloxy, cycloalkynylcarbonyloxy, arylcarbonyloxy, hetarylcarbonyloxy, heterocyclylcarbon-yloxy, alkylcarbonylamino, alkenylcarbonylamino, alkynyl-carbonylamino, cycloalkylcarbonylamino, cycloalkenyl-carbonylamino, cycloalkynylcarbonylamino, arylcarbonyl-amino, hetarylcarbonylamino, heterocyclylcarbonylamino, cycloalkylalkoxy,cycloalkenylalkoxy,cycloalkynylalkoxy, arylalkoxy, hetarylalkoxy or heterocyclylalkoxy, R10 may be substituted by 1-4 identical or different substituents R11, and R10 is hydrogen, halogen, cyano, nitro, haloalkyl, alkyl, haloalkoxy, alkenyl, alkynyl, cycloalkyl, aryl, hetaryl, heterocyclyl, cycloalkenyl, - 101 - O.Z. 0050/43411 cycloalkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalk-oxy, aryloxy, hetaryloxy, heterocyclyloxy, cycloalkenyl-oxy, cycloalkynyloxy, alkoximino, alkenyloximino, alkynyloximino,cycloalkyloximino,cyclocoalkenyloximino, cycloalkynyloximino, aryloximino, hetaryloximino, hetero-cyclyloximino, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl,cycloalkoxycarbonyl,aryloxycarbonyl, hetaryloxycarbonyl, heterocyclyloxycarbonyl, cyclo-alkenyloxycarbonyl, cycloalkynyloxycarbonyl, alkyl-aminocarbonyl, dialkylaminocarbonyl, alkenylamino-carbonyl, dialkenylaminocarbonyl, alkynylaminocarbonyl, dialkynylaminocarbonyl, cycloalkylaminocarbonyl, cycloalkenylaminocarbonyl, cycloalkynylaminocarbonyl, arylaminocarbonyl, hetarylaminocarbonyl, heterocyclylaminocarbonyl, alkylthio, alkenylthio, alkynylthio, cycloalkylthio, arylthio, hetarylthio, heterocyclylthio, cycloalkenylthio, cycloalkynylthio, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, arylamino, hetarylamino, heterocyclylamino, cycloalkenylamino, cycloalkynylamino, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, hetarylcarbonyl, heterocyclylcarbonyl, cycloalkenylcarbonyl, cycloalkynylcarbonyl, alkylsulfox-yl, alkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl, arylsulfoxyl, hetarylsulfoxyl, heterocyclylsulfoxyl, cycloalkynylsulfoxyl, cycloalkenylsulfoxyl, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, hetarylsulfonyl, heterocyclylsulfonyl, cycloalkenylsulfonyl, cylcoalkynylsulfonyl, alkylsulfinyl, alkenylsulfinyl, alkynylsulfinyl, cycloalkylsulfinyl, arylsulfinyl, hetarylsulfinyl, heterocyclylsulfinyl, cycloalkenyl-sulfinyl, cycloalkynylsulfinyl, alkylcarbonyloxy, alkenylcarbonyloxy,alkynylcarbonyloxy,cycloalkylcarbon-yloxy, cycloalkenylcarbonyloxy, cycloalkynylcarbonyloxy, arylcarbonyloxy, hetarylcarbonyloxy, heterocyclylcarbon-yloxy, alkylcarbonylamino, alkenylcarbonylamino, alkynyl-- 102 - O.Z. 0050/43411 carbonylamino, cycloalkylcarbonylamino, cycloalkenyl-carbonylamino, cycloalkynylcarbonylamino, arylcarbonyl-amino, hetarylcarbonylamino, heterocyclylcarbonylamino, cycloalkylalkoxy,cycloalkenylalkoxy,cycloalkynylalkoxy, arylalkoxy, hetarylalkoxy or heterocyclylalkoxy, R11 may be substituted and is hydrogen, halogen, cyano, nitro, haloalkyl, alkyl, haloalkoxy, alkenyl, alkynyl, cycloalkyl, aryl, hetaryl, heterocyclyl, cycloalkenyl, cycloalkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalk-oxy, aryloxy, hetaryloxy, heterocyclyloxy, cycloalkenyl-oxy, cycloalkynyloxy, alkoximino, alkenyloximino, alkynyloximino, cycloalkoximino, cycloalkenyloximino, cycloalkynyloximino, aryloximino, hetaryloximino, hetero-cyclyloximino, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl,cycloalkoxycarbonyl,aryloxycarbonyl, hetaryloxycarbonyl, heterocyclyoxycarbonyl, cycloalkenyloxycarbonyl, cycloalkynyloxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkenylaminocarbonyl, dialkenylaminocarbonyl, alkynylaminocarbonyl, dialkynylaminocarbonyl, cycloalkylaminocarbonyl, cycloalkenylaminocarbonyl, cycloalkynylaminocarbonyl, arylaminocarbonyl, hetarylaminocarbonyl, heterocyclylaminocarbonyl, alkyl-thio, alkenylthio, alkynylthio, cycloalkylthio, arylthio, hetarylthio, heterocyclylthio, cycloalkenylthio, cyclo-alkynylthio, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, arylamino, hetarylamino, heterocyclyl-amino, cycloalkenylamino, cycloalkynylamino, alkylcarbon-yl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, hetarylcarbonyl, heterocyclylcarbonyl, cycloalkenylcarbonyl, cycloalkynylcarbonyl, alkylsulfox-yl, alkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl, arylsulfoxyl, hetarylsulfoxyl, heterocyclylsulfoxyl, cycloalkynylsulfoxyl,cycloalkenylsulfoxylalkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, hetarylsulfonyl, heterocyclylsulfonyl, cycloalkenylsulfonyl, cycloalkynylsulfonyl, - 103 - O.Z. 0050/43411 alkylsulfinyl, alkenylsulfinyl, alkynylsulfinyl, cycloalkylsulfinyl, arylsulfinyl, hetarylsulfinyl, heterocyclylsulfinyl, cycloalkenylsulfinyl, cycloalkynylsulfinyl, alkylcarbonyloxy, alkenylcarbonyloxy,alkynylcarbonyloxy,cycloalkylcarbon-yloxy, cycloalkenylcarbonyloxy, cycloalkynylcarbonyloxy, arylcarbonyloxy, hetarylcarbonyloxy, heterocyclylcarbon-yloxy, alkylcarbonylamino, alkenylcarbonylamino, alkynyl-carbonylamino, cycloalkylcarbonylamino, cycloalkenyl-carbonylamino, cycloalkynylcarbonylamino, arylcarbonyl-amino, hetarylcarbonylamino, heterocyclylcarbonylamino, cycloalkylalkoxy,cycloalkenylalkoxy,cycloalkynylalkoxy, arylalkoxy, hetarylalkoxy or heterocyclylalkoxy, or an acid addition product or base addition product of this compound.
11. A method for controlling fungi, wherein the fungi or the plants, seed or materials threatened by fungal attack or the soil is or are treated with a fungicidal amount of a compound of the formula I
I

where B is alkyl which is substituted by 1-4 identical or different substituents R3, alkenyl which is substituted by 1-4 identical or different substituents R4, alkynyl which is substituted by 1-4 identical or different substituents R5, cycloalkyl which is substituted by 1-4 identical or different substituents R6, cycloalkenyl which is substituted by 1-4 identical or different substituents R7, cycloalkynyl which is substituted by 1-4 identical or different substituents R8 or heterocyclyl which is - 104 - O.Z. 0050/43411 substituted by 1-4 identical or different eubstituents R8, X and Y independently of one another are each hydrogen, halogen, cyano, nitro, haloalkyl, alkyl, haloalkoxy, alkenyl, alkynyl, cycloalkyl, aryl, hetaryl, heterocycl-yl, cycloalkenyl, cycloalkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, aryloxy, hetaryloxy, hetero-cyclyloxy, cycloalkenyloxy, cycloalkynyloxy, alkoximino, alkenyloximino, alkynyloximino, cycloalkyloximino, cycloalkenyloximino, cycloalkynyloximino, aryloximino, hetaryloximino, heterocycyloximino, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, cycloalkyloxy-carbonyl aryloxycarbonyl, hetaryloxycarbonyl, hetero-cyclyloxycarbonyl,cycloalkenyloxycarbonyl,cycloalkynyl-oxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkenylaminocarbonyl, dialkenylaminocarbonyl, alkynyl-aminocarbonyl, dialkynylaminocarbonyl, cycloalkylamino-carbonyl, cycloalkenylaminocarbonyl, cycloalkynylamino-carbonyl, arylaminocarbonyl, hetarylaminocarbonyl, heterocyclylaminocarbonyl, alkylthio, alkenylthio, alkynylthio, cycloalkylthio, arylthio, hetarylthio, heterocyclylthio, cycloalkenylthio, cycloalkynylthio, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, arylamino, hetarylamino, heterocyclylamino, cycloalkenyl-amino, cycloalkynylamino, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, het-arylcarbonyl,heterocyclylcarbonyl,cycloalkenylcarbonyl, cycloalkynylcarbonyl, alkylsulfoxyl, alkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl, arylsulfoxyl, hetarylsulfoxyl, heterocyclylsulfoxyl, cycloalkynyl-sulfoxyl, cycloalkenylsulfoxyl, alkylsulfonyl, alkenyl-sulfonyl, alkynylsulfonyl, cycloalkylsulfonyl, aryl-sulfonyl, hetarylsulfonyl, heterocyclylsulfonyl, cyclo-alkenylsulfonyl, cycloalkynylsulfonyl, alkylsulfinyl, alkenylsulfinyl, alkynylsulfinyl, cycloalkylsulfinyl, arylsulfinyl, hetarylsulfinyl, heterocyclylsulfinyl, cycloalkenylsulfinyl, cycloalkynylsulfinyl, alkyl-carbonyloxy, alkenylcarbonyloxy, alkynylcarbonyloxy, - 105 - O.Z. 0050/43411 cycloalkylcarbonyloxy, cycloalkenylcarbonyloxy, cyclo-alkynylcarbonyloxy, arylcarbonyloxy, hetarylcarbonyloxy, heterocyclylcarbonyloxy, alkylcarbonylamino, alkenyl-carbonylamino, alkynylcarbonylamino, cycloalkylcarbonyl-amino, cycloalkenylcarbonylamino, cycloalkynylcarbonyl-amino, arylcarbonylamino, hetarylcarbonylamino, hetero-cyclylcarbonylamino, cycloalkylalkoxy, cycloalkenyl-alkoxy, cylcoalkynylalkoxy, arylalkoxy, hetarylalkoxy or heterocyclylalkoxy, if X and Y are on adjacent carbon atoms, they may be condensed to form an unsubstituted or substituted aroma-tic or heteroaromatic, alicyclic or heterocyclic, par-tially or completely hydrogenated ring, R1 and R2 may be substituted and independently of one another are each alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl, R3 and R4 may be substituted by 1-4 identi-cal or different substituents R10, and R3 and R4 are each nitro, haloalkoxy, alkoxy, alkynyl, cycloalkyl, hetaryl, heterocyclyl, cycloalkenyl, cycoalkynyl, alkenyloxy, alkynyloxy, cycloalkoxy, hetaryloxy, heterocyclyloxy, cycloalkenyloxy, cycloalkynyloxy, alkoximino, alkenyl-oximino, alkynyloximino, cycloalkyloximino, cycloalkenyl-oximino, cycloalkynyloximino, aryloximino, hetarylox-imino, heterocyclyloximino, cycloalkyloxycarbonyl aryloxycarbonyl, hetaryloxycarbonyl, heterocyclyloxy-carbonyl, cycloalkenyloxycarbonyl, cycloalkynyloxy-carbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkenylaminocarbonyl, dialkenylaminocarbonyl, alkynyl-aminocarbonyl, dialkynylaminocarbonyl, cycloalkylamino-carbonyl, cycloalkenylaminocarbonyl, cycloalkynylamino-carbonyl, arylaminocarbonyl, hetarylaminocarbonyl, heterocyclylaminocarbonyl, alkylthio, alkenylthio, alkynylthio, cycloalkylthio, arylthio, hetarylthio, heterocyclylthio, cycloalkenylthio, cycloalkynylthio, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, arylamino, hetarylamino, heterocyclylamino, cycloalkenyl-amino, cycloalkynylamino, alkylcarbonyl, alkenylcarbonyl, - 106 - O.Z. 0050/43411 alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, het-arylcarbonyl,heterocyclylcarbonyl,cycloalkenylcarbonyl, cycloalkynylcarbonyl, alkylsulfoxyl, alkenylsulfoxyl, cycloalkylsulfoxyl, arylsulfoxyl, hetarylsulfoxyl, heterocyclylsulfoxyl,cycloalkynylsulfoxyl,cycloalkenyl-sulfoxyl, alkylsulfonyl, alkenylsulfonyl, alkynyl-sulfonyl, cycloalkylsulfonyl, arylsulfonyl, hetaryl-sulfonyl, heterocyclylsulfonyl, cycloalkenylsulfonyl, cycloalkynylsulfonyl, alkylsulfinyl, alkenylsulfinyl, alkynylsulfinyl, cycloalkylsulfinyl, arylsulfinyl, hetarylsulfinyl, heterocyclylsulfinyl, cycloalkenyl-sulfinyl, cycloalkynylsulfinyl, alkylcarbonyloxy, alkenylcarbonyloxy,alkynylcarbonyloxy,cycloalkylcarbon-yloxy, cycloalkenylcarbonyloxy, cycloalkynylcarbonyloxy, arylcarbonyloxy, hetarylcarbonyloxy, heterocyclylcarbon-yloxy, alkylcarbonylamino, alkenylcarbonylamino, alkynyl-carbonylamino, cycloalkylcarbonylamino, cycloalkenyl-carbonylamino, cycloalkynylcarbonylamino, arylcarbonyl-amino, hetarylcarbonylamino, heterocyclylcarbonylamino, cycloalkylalkoxy,cycloalkenylalkoxy,cycloalkynylalkoxy, hetarylalkoxy, heterocyclylalkoxy, alkynylalkenyl, cyclo-alkylalkenyl, cycloalkenylalkenyl, cycloalkynylalkenyl, hetarylalkenyl, heterocyclylalkenyl, alkoximinoalkyl, alkenyloximinoalkyl, alkynyloximinoalkyl, cycloalkox-iminoalkyl, cycloalkenyloximinoalkyl, cycloalkynylox-iminoalkyl, aryloximinoalkyl, hetaryloximinoalkyl, heterocyclyloximinoalkyl, alkoximinoalkenyl, alkenylox-iminoalkenyl, alkynyloximinoalkenyl, cycloalkoximino-alkenyl,cycloalkenyloximinoalkenyl,cycloalkynyloximino-alkenyl, aryloximinoalkenyl, hetaryloximinoalkenyl or heterocyclyloximinoalkenyl, R5, R6, R7 and R8 may be substituted by 1-4 identical or different substituents R10, and R5, R6, R7 and R8 are each nitro, haloalkyl, alkyl, haloalkoxy, alkenyl, alkynyl, cycloalkyl, aryl, hetaryl, heterocyclyl, cycloalkenyl, cycloalkynyl, alkoxy, alkenyloxy, alkynyloxy, cyclo-alkoxy, aryloxy, hetaryloxy, heterocyclyloxy, cyclo-- 107 - O.Z. 0050/43411 alkenyloxy, cycloalkynyloxy, alkoximino, alkenyloximino, alkynyloximino, cycloalkoximino, cycloalkenyloximino, cycloalkynyloximino, aryloximino, hetaryloximino, hetero-cyclyloximino, cycloalkoxycarbonyl, aryloxycarbonyl, het-aryloxycarbonyl,heterocyclyoxycarbonyl,cycloalkenyloxy-carbonyl, cycloalkynyloxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkenylaminocarbonyl, dialkenyl-aminocarbonyl, alkynylaminocarbonyl, dialkynylamino-carbonyl, cycloalkylaminocarbonyl, cycloalkenylamino-carbonyl, cycloalkynylaminocarbonyl, arylaminocarbonyl, hetarylaminocarbonyl, heterocyclylaminocarbonyl, alkyl-thio, alkenylthio, alkynylthio, cycloalkylthio, arylthio, hetarylthio, heterocyclylthio, cycloalkenylthio, cyclo-alkynylthio, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, arylamino, hetarylamino, heterocyclyl-amino, cycloalkenylamino, cycloalkynylamino, alkylcarbon-yl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, hetarylcarbonyl, heterocyclylcarbonyl, cycloalkenylcarbonyl, cycloalkynylcarbonyl, alkylsulfox-yl, alkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl, arylsulfoxyl, hetarylsulfoxyl, heterocyclylsulfoxyl, cycloalkynylsulfoxyl, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, hetarylsulfonyl, heterocyclylsulfonyl, cycloalkenyl-sulfonyl, cycloalkynylsulfonyl, alkylsulfinyl, alkenyl-sulfinyl, alkynylsulfinyl, cycloalkylsulfinyl, aryl-sulfinyl, hetarylsulfinyl, heterocyclylsulfinyl, cyclo-alkanylsulfinyl, cycloalkynylsulfinyl, alkylcarbonyloxy, alkenylcarbonyloxy,alkynylcarbonyloxy,cycloalkylcarbon-yloxy, cycloalkenylcarbonyloxy, cycloalkynylcarbonyloxy, arylcarbonyloxy, hetarylcarbonyloxy, heterocyclylcarbon-yloxy, alkylcarbonylamino, alkenylcarbonylamino, alkynyl-carbonylamino, cycloalkylcarbonylamino, cycloalkenyl-carbonylamino, cycloalkynylcarbonylamino, arylcarbonyl-amino, hetarylcarbonylamino or heterocyclylcarbonylamino, R9 may be substituted by 1-4 identical or different substituents R10, and R9 is hydrogen, halogen, cyano, - 108 - O.Z. 0050/43411 nitro, haloalkyl, alkyl, haloalkoxy, alkenyl, alkynyl, cycloalkyl, aryl, hetaryl, heterocyclyl, cycloalkenyl, cycloalkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalk-oxy, aryloxy, hotaryloxy, heterocyclyloxy, cycloalkenyl-oxy, cycloalkynyloxy, alkoximino, alkenyloximino, alkynyloximino,cycloalkyloximino,cyclocoalkenyloximino, cycloalkynyloximino, aryloximino, hetaryloximino, hetero-cyclyloximino, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxyxarbonyl,cycloalkoxycarbonyl,aryloxycarbonyl, hetaryloxycarbonyl, heterocyclyloxycarbonyl, cycloalkenyloxycarbonyl, cycloalkynyloxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkenylaminocarbonyl, dialkenylaminocarbonyl, alkynylaminocarbonyl, dialkynylaminocarbonyl, cycloalkylaminocarbonyl, cycloalkenylaminocarbonyl, cycloalkynylaminocarbonyl, arylaminocarbonyl, hetarylaminocarbonyl, heterocyclylaminocarbonyl, alkyl-thio, alkenylthio, alkynylthio, cycloalkylthio, arylthio, hetarylthio, heterocyclylthio, cycloalkenylthio, cyclo-alkynylthio, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, arylamino, hetarylamino, heterocyclyl-amino, cycloalkenylamino, cycloalkynylamino, alkylcarbon-yl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, hetarylcarbonyl, heterocyclylcarbonyl, cycloalkenylcarbonyl, cycloalkynylcarbonyl, alkylsulfox-yl, alkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl, arylsulfoxyl, hetarylsulfoxyl, heterocyclylsulfoxyl, cycloalkynylsulfoxyl, cycloalkenylsulfoxyl, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, hetarylsulfonyl, heterocyclylsulfonyl, cycloalkenylsulfonyl, cycloalkynylsulfonyl, alkylsulfinyl, alkenylsulfinyl, alkynylsulfinyl, cycloalkylsulfinyl, arylsulfinyl, hetarylsulfinyl, heterocyclylsulfinyl, cycloalkenyl-sulfinyl, cycloalkynylsulfinyl, alkylcarbonyloxy, alkenylcarbonyloxy,alkynylcarbonyloxy,cycloalkylcarbon-yloxy, cycloalkenylcarbonyloxy, cycloalkynylcarbonyloxy, - 109 - O.Z. 0050/43411 arylcarbonyloxy, hetarylcarbonyloxy, heterocyclylcarbon-yloxy, alkylcarbonylamino, alkenylcarbonylamino, alkynyl-carbonylamino, cycloalkylcarbonylamino, cycloalkenyl-carbonylamino, cycloalkynylcarbonylamino, arylcarbonyl-amino, hetarylcarbonylamino, heterocyclylcarbonylamino, cycloalkylalkoxy,cycloalkenylalkoxy,cycloalkynylalkoxy, arylalkoxy, hetarylalkoxy or heterocyclylalkoxy, R10 may be substituted by 1-4 identical or different substituents R11, and R10 is hydrogen, halogen, cyano, nitro, haloalkyl, alkyl, haloalkoxy, alkenyl, alkynyl, cycloalkyl, aryl, hetaryl, heterocyclyl, cycloalkenyl, cycloalkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalk-oxy, aryloxy, hetaryloxy, heterocyclyloxy, cycloalkenyl-oxy, cycloalkynyloxy, alkoximino, alkenyloximino, alkynyloximino,cycloalkyloximino,cyclocoalkenyloximino, cycloalkynyloximino, aryloximino, hetaryloximino, hetero-cyclyloximino, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl,cycloalkoxycarbonyl,aryloxycarbonyl, hetaryloxycarbonyl, heterocyclyloxycarbonyl, cycloalkenyloxycarbonyl, cycloalkynyloxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkenylaminocarbonyl, dialkenylaminocarbonyl, alkynylaminocarbonyl, dialkynylaminocarbonyl, cycloalkylaminocarbonyl, cycloalkenylaminocarbonyl, cycloalkynylaminocarbonyl, arylaminocarbonyl, hetarylaminocarbonyl, heterocyclylaminocarbonyl, alkyl-thio, alkenylthio, alkynylthio, cycloalkylthio, arylthio, hetarylthio, heterocyclylthio, cycloalkenylthio, cyclo-alkynylthio, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, arylamino, hetarylamino, heterocyclyl-amino, cycloalkenylamino, oycloalkynylamino, alkylcarbon-yl, alkenylcarbonyl, alkynylcarbonyl,cycloalkylcarbonyl, arylcarbonyl, hetarylcarbonyl, heterocyclylcarbonyl, cycloalkenylcarbonyl, cycloalkynylcarbonyl, alkylsulfox-yl, alkonylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl, arylsulfoxyl, hetarylsulfoxyl, heterocyclylsulfoxyl, cycloalkynylsulfoxyl, cycloalkenylsulfoxyl, - 110 - O.Z. 0050/43411 alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, hetarylsulfonyl, heterocyclylsulfonyl, cycloalkenylsulfonyl, cycloalkynylsulfonyl, alkylsulfinyl, alkenylsulfinyl, alkynylsulfinyl, cycloalkylsulfinyl, arylsulfinyl, hetarylsulfinyl, heterocyclylsulfinyl, cycloalkenyl-sulfinyl, cycloalkynylsulfinyl, alkylcarbonyloxy, alkenylcarbonyloxy,alkynylcarbonyloxy,cycloalkylcarbon-yloxy, cycloalkenylcarbonyloxy, cycloalkynylcarbonyloxy, arylcarbonyloxy, hetarylcarbonyloxy, heterocyclylcarbon-yloxy, alkylcarbonylamino, alkenylcarbonylamino, alkynyl-carbonylamino, cycloalkylcarbonylamino, cycloalkenyl-carbonylamino, cycloalkynylcarbonylamino, arylcarbonyl-amino, hetarylcarbonylamino, heterocyclylcarbonylamino, cycloalkylalkoxy,cycloalkenylalkoxy,cycloalkynylalkoxy, arylalkoxy, hetarylalkoxy or heterocyclylalkoxy, R11 may be substituted and is hydrogen, halogen, cyano, nitro, haloalkyl, alkyl, haloalkoxy, alkenyl, alkynyl, cycloalkyl, aryl, hetaryl, heterocyclyl, cycloalkenyl, cycloalkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalk-oxy, aryloxy, hetaryloxy, heterocyclyloxy, cycloalkenyl-oxy, cycloalkynyloxy, alkoximino, alkenyloximino, alkynyloximino, cycloalkoximino, cycloalkenyloximino, cycloalkynyloximino, aryloximino, hetaryloximino, hetero-cyclyloximino, alkoxycarbonyl, alkenylcarbonyl, alkynyloxycarbonyl,cycloalkoxycarbonyl,aryloxycarbonyl, hetaryloxycarbonyl, heterocyclyloxycarbonyl, cycloalkenyloxycarbonyl, cycloalkynyloxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkenylaminocarbonyl, dialkenylaminocarbonyl, alkynylaminocarbonyl, dialkynylaminocarbonyl, cycloalkylaminocarbonyl, cycloalkenylaminocarbonyl, cycloalkynylaminocarbonyl, arylaminocarbonyl, hetarylaminocarbonyl, heterocyclylaminocarbonyl, alkyl-thio, alkenylthio, alkynylthio, cycloalkylthio, arylthio, hetarylthio, heterocyclylthio, cycloalkenylthio, cyclo-alkynylthio, alkylamino, alkenylamino, alkynylamino, - 111 - O.Z. 0050/43411 cycloalkylamino, arylamino, hetarylamino, heterocyclyl-amino, cycloalkenylamino, cycloalkynylamino, alkylcarbon-yl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, hetarylcarbonyl, heterocyclylcarbonyl, cycloalkenylcarbonyl, cycloalkynylcarbonyl, alkylsulfox-yl, alkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl, arylsulfoxyl, hetarylsulfoxyl, heterocyclylsulfoxyl, cycloalkynylsulfoxyl, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, hetarylsulfonyl, heterocyclylsulfonyl, cycloalkenyl-sulfonyl, cycloalkynylsulfonyl, alkylsulfinyl, alkenyl-sulfinyl, alkynylsulfinyl, cycloalkylsulfinyl, aryl-sulfinyl, hetarylsulfinyl, heterocyclylsulfinyl, cyclo-alkenyl sulfinyl, cycloalkynylsulfinyl, alkylsulfinyl, alkenylsulfinyl, alkynylsulfinyl, cycloalkylsulfinyl, arylsulfinyl, hetarylsulfinyl, heterocyclylsulfinyl, cycloalkenylsulfinyl, cycloalkynylsulfinyl, alkyl-carbonyloxy, alkenylcarbonyloxy, alkynylcarbonyloxy, cycloalkylcarbonyloxy, cycloalkenylcarbonyloxy, cyclo-alkynylcarbonyloxy, arylcarbonyloxy, hetarylcarbonyloxy, heterocyclylcarbonyloxy, alkylcarbonylamino, alkenyl-carbonylamino, alkynylcarbonylamino, cycloalkylcarbonyl-amino, cycloalkenylcarbonylamino, cycloalkynylcarbonyl-amino, arylcaxbonylamino, hetarylcarbonylamino, hetero-cyclylcarbonylamino, cycloalkylalkoxy, cycloalkenylalkoxy, cycloalkynylalkoxy, arylalkoxy, hetarylalkoxy or heterocyclylalkoxy, or an acid addition product or base addition product of this compound.
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DE19519041A1 (en) * 1995-05-24 1996-11-28 Basf Ag Azolyloxybenzyl alkoxyacrylic acid esters, process for their preparation and their use
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