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AU660226B2 - Substituted acrylates and crop protection agents containing them - Google Patents

Substituted acrylates and crop protection agents containing them Download PDF

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Publication number
AU660226B2
AU660226B2 AU42121/93A AU4212193A AU660226B2 AU 660226 B2 AU660226 B2 AU 660226B2 AU 42121/93 A AU42121/93 A AU 42121/93A AU 4212193 A AU4212193 A AU 4212193A AU 660226 B2 AU660226 B2 AU 660226B2
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AU
Australia
Prior art keywords
amino
cycloalkenyl
substituted
alkenyl
alkynyl
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AU42121/93A
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AU4212193A (en
Inventor
Eberhard Ammermann
Hartmann Koenig
Gisela Lorenz
Bernd Mueller
Franz Roehl
Hubert Sauter
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BASF SE
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BASF SE
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Publication of AU4212193A publication Critical patent/AU4212193A/en
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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
    • C—CHEMISTRY; METALLURGY
    • 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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    • C07D—HETEROCYCLIC COMPOUNDS
    • 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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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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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    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
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    • C07D277/20—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
    • 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

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Environmental Sciences (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Epoxy Compounds (AREA)
  • Pyrrole Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Pyridine Compounds (AREA)

Description

/UUU 11 28/3/Ia Regulallon 3.2(2)
AUSTRALIA
Patents Act 1990 660226
ORIGINAL
COMPLETE SPECIFICATION STANDARD PATENT Application Number: Lodged:
U
Invention Title: SUBSTITUTED ACRYLATES AND CROP PROTECTION AGENTS CONTAINING THEM The following statement is a full description of this invention, including the best method of performing it known to :-US S3' 0.2. 0050/43411 Substituted acrylates and crop protection agents containing them The present invention relates to substituted acrylates and their use as crop protection agents, in particular for controlling fungi, insects, nematodes and spider mites.
It is known that acrylates, for example methyl a- (2-hydroxyphenyl)-B-methoxyacrylate (EP 251 082, EP 178 826) can be used as fungicides. However, their fungicidal action is unsatisfactory.
We have found, surprisingly, that substituted acrylates of the formula I X Y
I
B
OR
2 0 2 where 15 B is alkyl which is substituted by 1-4 identical or different substituents R 3 alkenyl which is substituted by 1-4 identical or different substituents R 4 alkynyl which .is substituted by 1-4 identical or different substituents R 5 1 cycloalkyl which is substituted by 1-4 identical or different substituents R 6 cycloalkenyl which is substituted by 1-4 identical or different substituents
R
7 cycloalkynyl which is substituted by 1-4 identical or different substituents R 8 or heterocyclyl which is substituted by 1-4 identical or different substituents R 9 X and Y independently of one another are each hydrogen, halogen, cyano, nitro, haloalkyl, alkyl, haloalkoxy, alkenyl, alkynyl, cycloalkyl, aryl, hetaryl, heterocyclyl, cycloalkenyl, cycloalkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, aryloxy, hetaryloxy, heterocyclyloxy, cycloalkenyloxy, cycloalkynyloxy, alkoximino, I 2 Z. 0050/43411 alkenyloximino, alkynyloximino, cycloalkyloximino, cycloalkenyloximino, cycloalkynyloximino, aryloximino, hetaryloximino, heterocyclyloximino, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, cycloalkoxycarbonyl aryloicycarbonyl, hetaryloxycarbonyl, heterocyclyloxycarbonyrl, cylcoalkenyloxycarbonyl, cycloalkynyloxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkenylaminocarbonyl, dialkenylaminocarbonyl, alkynylaminocarbonyl, dialkynylaminocarbonyl, cycloalkylaminocarbon~ cycloalkenylaminocarbonyl, cyc loalkynyl aminocarbonyl, arylaminocarbonyl, hetarylaminocarbonyl, heterocyclylaminocarbonyl, alkyithic, a1ksnylthio, alky3nylthio, cycloalkylthio, arylthio, hetarylthio, heterocyclylthio, cycloalkenylthio, cycloalkynylthio, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, arylamino, hetarylamino, heterocyclylamino, cycloalkerylamino, cyc-loalkynylamino, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, hetarylcarbonyl, heterocyclylcarbonyl, cycloalkenylcarbonyl, 20 cycloalkynylcarbonyl, alkylsulfoxyl, alkenylsulfoxyl, alkynylsulfoxyl, dycloalkylsulfoxyl, arylsulfoxyl, *.:hetarylsulfoxyl, heterocyclylsulfoxyl, cycloalkynylsulfoxyl, cycloalkenylsulfoxyl, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, hetarylsulfonyl, heterocyclylsulfonyl, cyclo- 00.. leysloy, ccolyysloy, aklufnl alkenylsulfinyl, cyalkynylsulfnyl, cyialkylsulfinyl, arylsulfinyl, hetarylsulfinyl, heterocyclylsulfinyl, 0 cycloalkenylsulfinyl, cycloalkynylsulfinyl, alkylcarbonyloxy, alkenylcarbony1oxy, alkynylcarbonyloxy, cycloalkylcarbonyloxy, cycloalkenylcarbonyloxy, cycloalkynylcarbonyloxy, aryicarbonyloxy, hetarylcarbonyloxy, heterocyclylcarbonyloxy, alkylcarbonylamino, alkenylcarbonylamino, alkynylcarbonylamino, cycloalkylcarbonylamino, cyc loalkenylc arbonyl amino, cycloalky nylcarbonylaimino, arylcarbonylamino, hetarylc arbonyl amino, heterocyclylcarbonylamino, cycloalkylalkoxy,, cycloalkenyl- 3 OZ. 0050/43411 alkoxy, cylcoalkynylalkoxy, arylalkoxy, hetarylalkoxy or heterocyclylalkoxy, if Xi and Y are on adjacent carbon atoms, they may be condensed to form an unsubstituted or substituted aromatic or heteroaromatic, alicyclic or heterocyclic, partially or completely hydrogenated ring,
R
1 and R 2 may be substituted and independently of one another are each alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl, R 3 and R 4 may be substituted by 1-4 identical or different substituents R 10 and R 3 and R 4 are each nitro, alkoxy, haloalkoxy, alkynyl, cycloalkyl, hetaryl, heterocyclyl, cycloalkenyl, cycloalkynyl, alkenyloxy, alkynyloxy, cycloalkoxy, hetaryloxy, het~rocyclyloxy, cycloalkenyloxy, cycloalkynyloxy, alkoximino, alkenyloximino, alkynyloximino, cycloalkoximino, cycloalkenyloximino, cycloalkynyloximino, aryloximino, hetaryloximino, heterocyclyloximino, cycloalkoxycarbonyl aryloxycarbonyl, hetaryloxycarbonyl, heterocyclyloxycarbonyl, cycloalk~enyloxycarbonyl, cycloalkynyloxy- *:20 carbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkenylaminocarbonyl, dialkenylaminocarbonyl, alkyny] aminocarbonyl, dialkynylaminocarbonyl, cycloalkylaminocarbonyl, cycloalkenylaminocarbonyl, cycloalkynylaminocarbonyl, arylaminocarbonyl, hetarylaininocarbonyl, heterooyclylaniinocarbonyl, alkylthio, alkenylthio, *alkynylthio, cycloalkylthio, arylthio, hetarylthio, heterocyclylthio, cycloalkenylthio, cycloalkynylthio, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, arylamino, hetarylamino, heterocyclylamino, cycloalkenylamino, cycloal..cynylamino, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, het- :arylcarbonyl, heterocyclylcarbonyl, cycloalkenylcarbonyl, cycloalkynylcarbonyl, alkylsulfoxyl, alkenylsulfoxyl, cycloalkylsulfoxyl, arylsulioxyl, hetarylsulfoxyl, heterocyclylsulf oxyl, cycloalkynylsulf oxyl, cycloalkenylsulfoxyl, alkylsulfonyl, alkenylsulfonyl. alkynylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, hetaryl- 4 O.Z. 0050/43411 sulfonyl, heterocyclylsulfonyl, cycloalkenylsulfonyl, cycloalkynylsulfonyl, alkylsulfinyl, a 1 ,-nylsulfinyl, alkynylsulfinyl, cyclco~1kylsulfiny1, arylsulfinyl, hetarylsulfinyl, heterocyclylsulfinyl, cycloalkenylsulfinyl, cycloalkynylsulfinyl, alkylcarbonyloxy, alkenylcarbonyloxy., alkynylcarbonyloxy, cycloalkylcarbonyloxy, cycloalkenyrlcarbonyloxy, cycloalkynylcarbonkyloxy, arylcarbonyloxy, hetarylcarbonyloxy, heterocyclylcarbonyloxy, alkylcarbonylamino, alkenylcarbonylamino, alkynylcarbonylamino, cycloalkylcarbonylaiino, cycloalkenylcarbonylamino, cycloalkynylcazbonylamino, arylcarbonylamino, hetarylcarbonylamino, heterocyclylcarbonylamino, cycloalkylalkoxy, cycloalkenylalkoxy, cycloalkynylalkoxy, hetarylalkoxy, heterocyclylalkoxy, alkynylalkenyl, cyc loalkylalkenyl, cycloalkenylalkenyl, cycloalkynylalkenyl, hetarylalkenyl, heterocyclylalkenyl, alkoximinoalkyl, alkenyloximinoalkyl, alkynyloxminoalkyl, cycloalkoximinoalkyl, cycloalkenyloximinoalkyl, cycloalkynyloximi-noalkyl, aryloximinoalkyl, hetaryloximinoalkyl, :20 heterocyclyloximinoalkyl, alkoxiiminoalkenyl, alkanyloxi m n a k n y a k n l o i i o l e n l y l a l o i i o ialkenyl, ylalknyloximinoalkenyl, cycloalkyoximinoalkenyl, aryloximinoalkenyl, hetaryloximinoalkanyl or heterocyc lyloximinoalkenyl, R 5, R6, R 7 and R 8 may be substituted by 1-4 identical or dif ferent substituents R 10 and R R 6
R
7 and R 8 are each nitro, haloalkyl, alkyl, haloalkoxy, alkenyl, alkynyl, cycloalkyl, aryl, hetaryl, heterocyclyl, cycloalkenyl, cycloalkynyl, alkoxy, 'ilkenyloxy, alkynyloxy, cycloalkoxy, aryloxy, hetaryloxy, heterocyclyloxy, cyclo- 4 :6 alkenyloxy, cycloalkynyloxy, alkoximino, alkenyloximino, :alkynyloximino, cycloalkoximino, cycloalkenyloximino, cycloalkynyloximino, aryloximino, hetaryloximino, hetero.cyclyloximino, cycloalkoxycarbonyl, aryloxycarbonyl, hetaryloxycarbonyl, heterocyclyoxycarbonyl, cycloalkenyloxycarbonyl, cycloalkynyloxycarbony., alkylaminocarbonyl, dialkylaminocarbonyl, alkenylaminocarbonyl, dialkenyl- 5 Z. 0050/43411 amirnocarbonyl, alkynylaminocarbonyl, dialkynylaminocarbonyl, cycloalkylaminocarbonyl, cycloalkenylaminocarbonyl, cycloalkynylaminocarbonyl, arylaminocarbonyl, hetarylaniinocarbonyl, heterocyclylaminocarbonyl, alkylthio, alkenyithic, alkynylthio, cycloalkyithic, arylthio, hetarylthio, heterocyclylthio, cycloalkenylthio, cyc loalkynylthio, alkylamino, alkenylamino, alkynylamino, cyc loalkyl amino, arylamino, hetarylamino, heterocyclylamino, cyc loalkenyl amino, cyc loalkynyl amino, alkylcarbonyl, alken-ylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, hetarylcarbonyl, heterocyclylcarbonyl, cycloalkenylcarbonyl, cycloalkynylcarbonyl, alkylsulfoxyl, alkenylsulfoxyl, alkynylsulfoxyl, cycloa3 k'-ylsulfoxyl, arylsulfoxyl, hetarylsulfoxyl, heterocyclylsulfoxyl, cycloalkynylsulfoxyl, cycloalkeny.Lsulfoxyl, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, hetarylsulfonyl, heterocyclylsulfonyl, cycloalkenylsulfonyl, cycloalkynylsulfonyl, alkylsulfinyl, alkenylsulfinyl, 0 .:20 alkynylsulfinyl, cycloalkylsulfinyl, arylsulfinyl, hetarylsulfinyl, heterocyclylsulfinyl, cycloalkenyl- :sulfinyl, cycloalkcynylsulfinyl, alkylcarbonyloxy, alkenylcarbonyloxy, alkynylcarbonyloxy, cycloal-kylcarbonyloxy, cycloalkenylcarbonyloxy, cycloalkynylcarbonyloxy, axrylcarbonyloxy, hetarylcarbonyloxy, heterocyclylcarbon- ::*:yloxy, aikylcarbonylamino, alkenylc arbonyl amino, alkynylcarbonylamino, cycloalkylcarbonylamino, cycloalkenylcarbonylamino, cyc loalkynylc arbonyl amino, arylcarbonylamino, hetarylcarbonylamino or heterocyclylcarbonylamino, R 9 may be substituted by 1-4 identical or different substituents R 10 and R 9 is hydrogen, halogen, cyano, :nitro, haloalkyl, alkyl, haloalkoxy, alkenyl, alkynyl, cycloalkyl, aryl, hetaryl, heterocyclyl, cycloalkenyl, cycloalkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, aryloxy, hetaryloxy, heterocyclyloxy, cycloalkenyloxy, cycloalkynyloxy, alkoximino, alkenyloximino, alkynyloximino, cyc loalkoximino, cyc loalkenyloximino, ii 6 O.Z. 0050/43411 cycloalkynyloximino, aryloximino, hetaryloximino, heterocyclyloximino, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, cycloalkoxycarbonyl, aryloxycarbonyl, hetaryloxycarbonyl, heterocyclyloxycarbonyl, cycloalkenyloxycarbonyl, cycloalkynyloxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkenylaminocarbonyl, dialkenylaminocarbonyl, alkynylaminocarbonyl, dialkynylaminocarbonyl, cycloalkylaminocarbonyl, cycloalkenylaminocarbonyl, cycloalkynylaminocarbonyl, arylaminocarbonyl, hetarylaminocarbonyl, heterocyclylaminocarbonyl, alkylthio, alkenylthio, alkynylthio, cyc1oalkylthio, arylthio, hetarylthio, heterocyclylthio, cycloalkenylthio, cycloalkynyithic, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, arylamino, hetarylamino, heterocyclylamino, cycloalkenylamino, cyc loalkynyl amino,, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, hetarylcarbonyl, heterocyclylcarbonyl, cycloalkenylcarbonyl, cycloalkynylcarbonyl, alkylsuif ox- *:20 yl, alkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl, arylsulfoxyl, hetarylsulfoxyl, heterocyclylsUlfoxyl, cycloalkynylsulfoxyl, cycloalkenylsulfoxyl, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, hetarylsulfonyl, heterocyclylsulfonyl, cycloalkenylsulfonyl, cycloalkynylsulfonyl, alkylsulf iny., alkenylsulf inyl, alkynylsulfinyl, cycloalkylsulfinyl, arylsulfinyl, hetary1sulf iny1, heterocyclylsulfinyl, cycloalkenylsulfinyl, cycloalkynylsulfinyl, alkylsulfinyl, alkenylsulfinyl, alkynylsulfinyl, cycloalkylsulfinyl, arylsulfinyl, hetarylsulfinyl, heterocyclylsulfinyl, *.:cycloalkenylsulfinyl, cycloailkynylsulfinyl, alkylcarbonyloxy, alkenylcarbonyloxy, alkynylcarbonyloxy, cycloalkylcarbonyloxy, cycloalkenylcarbonyloxy, cycloalkynylcarbonyloxy, arylcarbonyloxy,, hetarylcarbonyloxy, heterocyclylcarbonyloxy, alkylcarbonyl amino, alkenylcarbonylamino, alkynylcarbonylamino, cycloaJlkylcarbonyl- I f O.Z. 0050/43411 amino, cycloalkenylcarbonylamino, cycloalkynylcarbonylamino, arylcarbonylamino, hetarylc arbonyl amino, heterocyclylcarbonylamino, cycloalkylalkoxy, cycloalkenylalkoxy, cycloalkynylalkoxy, arylalkoxy, hetarylalkoxy or heterocyclylalkoxy,
R
10 may be substituted by 1-4 identical or different substituents R 11 and R1 0 is hydrogen, halogen, cyano, nitro, haloalkyl, alkyl, haloalkoxy, alkenyl, alkynyl, cycloalkyl, aryl, hetaryl, heterocyclyl, cycloalkenyl, cycloalkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, aryloxy, hetaryloxy, heterocyclyloxy, cycloalkenyloxy, cycloalkynyloxy, alkoximino, alkenyloximino, alkynyloximino, cycloalkoximino, cycloalkenyloximino, cycloalkynyloximino, aryloximino, hetaryloximino, heterocyclyloximino, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, cycloalkoxycarbonyl, aryloxycarbonyl, hetaryloxycarbonyl, heterocyclyloxycarbonyl, cycloalkenyloxycarbonyl, cycloalkynyloxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, :20 alkenylaminocarbonyl, dialkenylaminocarbonyl, alkynylaminocarbonyl, dialkynylaminocarbonyl, :cycloalkylaminocarbonyl, cycloalkenylaminocarbonyl1, cycloalkynylaminocarbonyl, arylaminocarbonyl, hetarylaminocarbonyl, heterocyclylaminocarbonyl, alkylthio, alkenylthio,, alkynylthio, cycloalkylthio, arylthio, hetarylthio, heterocyclylthio, cycloalkenylthio, cycloalkynylthio, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, arylamino, hetaryl amino, heterocyc lylamino, cyc loalkenyl amino, cycloalkynylamino, alkylcarbonyl, alkenylc--arbonyl, alkynylcarbonyl, cycloalkylcarbonyl, 4~'jarylcarbonyl, hetarylcarbonyl, heterocyclylcarbonyl, cycloalkenylcarbonyl, cycloalkynylcarbonyl alkylsulfoxyl, alkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl, arylsulfoxyl, hetarylsulfoxyl, heterocyclylsulfoxyl, cycloalkynylsulfoxyl, cycloalkenylsulfoxyl, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, hetarylsulfonyl, 8 O.Z. 0050/43411 hdterocyclylsulfonyl, cycloalkenylsulfonyl, cycloalkynylsulfonyl, alkylsulfinyl, alkenylsulfinyl, alkynylsulfinyl, cycloalkylsulfinyl, arylsulfinyl, hetarylsulfinyl, heterocyclylsulfinyl, cycloalkenylsulfinyl, cycloalkynylsulfinyl, alkylcarbonyloxy, alkenylcarbonyloxy, alkynylcarbonyloxy, cycloalkylcarbonyloxy, cycloalkenylcarbonyloxy, cycloalkynylcarbonyloxy, arylcarbonyloxy, hetarylcarbonyloxy, heterocyclylcarbonyloxy, alkylc arbonyl amino, alkenylcarbonylamino, alkynylcarbonylamino, cycloalkylcarbonylamino, cycloalkenylcarbonylamino, cycioalkynylcarbonylamino, arylcarbonylamino, hetarylcarbonylamino, heterocyc lylc arbonyl amino, cycloalkylalkoxy, cycloalkenylalkoxy, cycloalkynylalkoxy, arylalkoxy, hetarylalkoxy or heterocyclylalkoxy, R"may be substituted and is hydrogen, halogen, cyano, nitro, haloalkyl, alkyl, haloalkoxy, alkenyl, alkynyl, cycloalkyl, aryl, hetaryl, heterocyclyl, cycloalkenyl, cycloalkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, aryloxyr, hetaryloxy, heterocyclyloxy, cycloalkenyloxy, cycloalkynyloxy, alkoximino, alkenyloximino, alkynyloximino, cycloalkyloximino, cycloalkenyloximino, cycloalkynyloximino, aryloximino, hetaryloximino, heterocyclyloximino, alkoxycarbonyl, alkenyloxycarbonyl, alky' nyloxycarbonyl, cycloalkoxycarbonyl, aryloxycarbonyl, hetaryloxycarbonyl, heterocyclyloxycarbonyl, cycloalkenyloxycarbonyl, cycloalkynyloxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkenylaminocarbonyl, dialkenylaminocarbanyl, ****alkynylaminocarbonyl, dialkynylaminocarbonyl, cycloalkylaniinocarbonyl, cycloalkenylaminocarbonyl, cycloalkynylaminocarbonyl, arylaminocarbonyl, hetarylaminocarbonyl, heterocyclylaminocarbonyl, alkylthio, alkenylthio, alkynylthio, cycloalkylthio, arylthio, hetarylthio, heterocyclylthio, cycloalkenyithic, cyc loalkynyithic, alkylamino, alkenylamino, alkynylamflno, cycloalky).amino, arylamino, hetarylamino, heterocyclylamino, cycloalkenylamino, cycloalkynylamino, alkyl- 9 Z. 0050/43411 carbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, hetarylcarbonyl, heterocyclylcarbonyl, cycloalkenylcarbonyl, cycloalkynylcarbonyl, alkylsulfoxyl, alkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl, arylsulfoxyl, hetarylsulfoxyl, heterocyclylsulfoxyl, cycloalkynylsulfoxyl, cycloalkenylsulfoxyl, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, hetarylsulfonyl, heterocyclylsulfonyl, cycloalkenylsulfonyl, cycloalkyny.1sulfanyl, alkylsulfinyl, alkenylsulfinyl, alkynylsulfinyl, cycloalkylsulfinyl, arylsulfinyl, hetarylsulfinyl, heterocyclylsulfinyl, cycloalkenylsulfinyl, cycloalkynylsulfinyl, alkylcarbonyloxy, alkenylcarbonyloxy, alkynylcarbonyloxy, cycloalkylcarbonyloxy, cycloalkenylcarbonyloxy, cycloalkynylcarbonyloxy, arylcarbonyloxy, hetarylcarbonyloxy, heterocyclylcarbonyloxy, alkylcarbonylarmino, alkenylcarbonyl amino, alkynylcarbonylamino, cycloalkylcarbonylamino, cycloalizenylcarbonylamino, cycloalkynylcarbonylamino, arylcarbonylamino, hetarylcarbonylamino, heterocyclylcarbonylaiino, 6 cycloalkylalkoxy, cycloalkenylalkoxy, cycloalkynylalkoxy, arylalkoxy, hetarylalkoxy or heterocyclylalkoxy, so*: and their plant-tolerated acid addition products and base 25 addition products not only have high fungitoxic, insecticidal*, nematocidal and acaricidal activity but also are very 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 4Y) nitric acid, or carboxylic acids, such as formic acid, :acetic acid, oxalic ac.AId, malonic acid, lactic acid, malic acid, succinic acid, tartaric acid, citric acid, salicylic acid, p-toluenesulfonic acid or dodecylbenT-nesulfonic acid, and also protic compounds generally, eq. saccharin.
Bases for base addition products are, for 10 10 Z. 0050/43411 example, potassium hydroxide, sodium hydroxide, potassium carbonate, sodium carbonate and ammonium hydroxide.
The novel compounds of the formula I may be obtained in the preparation as mixtures of stereoisomers (E/Z isomers, diastereomers, enantiomers), which can be separated into the individuAl components in a conventional manner, for example by crystallization or chromatography. Both the individual isomers and mixtures thereof can be used as fungicides, acaricides, nematocides Or insecticides and are embraced by the present invention.
The stated alkyl radicals are preferably of 1-10 carbon atoms, are substituted or unsubstituted and are, for example, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, pentyl, pent-l-yl, pent-2-yi, pent-3-yl, 2-methylbut-l-yl, 2methylbut-2-yl, 2-methylbut-3-yl, 3-methylbut-l-yl, 2,2dimethylprop-l-yl, hexyl, hex-1-yl, hex-2-yl, hex-3.-yl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methyl- Spentyl, 1, 1-dimethylbutyl, 1 ,2-dimethylbutyl, 1,3dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1, 2-trimethylpropyl, 1,2, 2-trimethylpropyl, l-ethyl-l-methylpropyl, 1-ethyl-2-methylpropyl, heptyl, hept-l.-yl, hept- 2yhept-3-yl, hept-4-yl, 1-methyihexyl, 2-methylhexyl, 3-methylhexyl, 4-methyihexyl, 5-methyihexyl, 1-ethylpentyl,'2-ethylpentyl, 3-ethylpentyl, 1-propylbutyl, 1isopropylbutyl, octyl, oct-1-yl, oct-2-yl, oct-3-yl, oct- 4*l e h l e t l e h l e p y 3 m t y h p y 4 4y-methylheptyl 2-methylheptyl, 3-methylheptyl, 4tyhexyl, 2-ethylhexyl, 3-ethyihexyl, 4-ethylhexyl, 1propylpentyl, 2-propylpentyl, nonyl, non-l-yl, non-2-yl, non-3-yl, non-4-yl, non-5-yl, 1-methyloctyl, 2-methyloctyl, 3-methyloctyl, 4-methyloctyl, 5-methyloctyl, 6methyloctyl, 7-methyloctyl, 4-methyl-2-propylpentyl, decyl, dec-l-yl, dec-2-yl, dec-3-yl, dec-4-yl, 1-ethyloctyl, 2-ethyloctyl, 3-ethyloctyl, 4-ethyloctyl, 6-ethyloctyl or 2-propylheptyl.
I
I
I
11 0050/43411 The stated alkenyl radicals are preferably of 2-10 carbon atoms, are unsubstituted or substituted and are, for example, 5 ethenyl, propenyl, 1-propenyl, 2propenyl, butenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1methyl-2-propenyl, 2-methyl-2-propenyl, pentenyl, 1pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl- 2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1.*1-dimethyl-2-propenyl, 1 ,2-dimethyl-2-propenyl, 1ethyl-2-propenyl, hexenyl, 1-hexenyl, 2-hexenyl, 3hexenyl, 4-hexenyl, 5-hexenyl, l-methyl-2-pentenyl, 2methyl-2 -pentenyl, 3-methyl-2-pentenyl, 4-methyl-2pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4methyl-4-pentenyl, 1, l-dimethyl-2-butenyl, 1, 1-dimethyl- 3-butenyl, 1, 2-dimethyl-2-butenyl, 1, 2-dimethyl-3butenyl, 3-dimethyl-2-butenyl, 1, 3-dimethyl-3-butenyl, 2-dimethyl-3-butenyl, 2 ,3-dimethyl-2-butenyl, 2,3dimethyl-3-butenyl, 3, 3-dimethyl-2-butenyl, 1-ethyl-2butenyl, 1-ethyl-3-butenyl, 2-ethyl-2-butenyl, 2-ethyl- 3-butenyl, 2-trimethyl-2-propenyl, 1-ethyl-i-methyl- 2-propenyl, heptenyl, octenyl, nonenyl or decenyl.
The stated alkynyl radicals are preferabyl of 2- 10 carbon atoms, are substituted or unsubstituted and are, f*Or example, ethyinyl, propynyl, 1-propynyl, 2propynyl, butynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1methyl-2-propynyl, pentynyl, 1-pentynyl, 2-pentynyl, 3- CA pentynyl, 4-.pentynyl, l-methyl-2-butynyl, 1-methyl-3butynyl, 2-methyl-3-butynyl, 1, 1-dimethyl-2-methyl-2- *pentynyl, hexynyl, l-methyl-3-pentynyl, 1-methyl-4pentynyl, 1-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3methyl-4-pentynyl, 4-methyl-2-pentynyl, 1 ,1-dimethyl-2butynyl, 1, 1-dimethyl-3-butynyl, 1, 2-dimethyl-3-butynyl, 2 ,2-dimethyl -3-butynyl, 1-ethyl-2-butynyl, l-ethyl-3butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl, heptynyl, octynyl, nonynyl, or decynyl.
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, cyclodecyl, bornanyl, norbonanyl, dicyclohexyl, bicyclo- [3.3.0]octyl, bicyclo[3.2.1]octyl, bicyclo[2.2.2Joctyl or bicyclo[3.3 ]nonyl.
The stated cycloalkenyl radicals are preferably of 3-10 carbon atoms, are unsubstituted or substituted and are, for example, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, cyclononenyl, cyclodecenyl, bornenyl, norbonenyl, bicyclo[3. 3.0)octenyl, bicyclo[3.2. 1]octenyl, bicyclo[2.2.2]octenyl or bicyclo[3.3.ljnonenyl.
The stated cycloalkynyl radicals Are preferably of 6-10 carbon atoms, are unsubstituted or substituted and are, for example, cyclohexyne, cycloheptyne, cyclooctyne, cyclononyne, cyclodecyne, cycloundecyne ozr cyclododecyne.
The stated haloalkyl radicals are preferably of 1-4 carbon atoms, are unsubstituted or substituted and are, for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethayl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-f luoroethyl, 2-f luoroethyl, 2, 2-difluoroethyl, 2,2, 2-trif luoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2, 2-dif luoroethyl, 2, 2-dichloro-2-f luoro- 30 ethyl, 2,2,2-trichloroethyl or pentafluoroethyl.
The stated aryl1 radicals are preferably of 6, or 14 carbon atoms, are unsubstituted or substituted and are, for example, phenyl, naphthyl, 1-naphthyl, 2naphthyl, anthracenyl, 1-anthracenyl, 2-anthracenyl or 9anthracenyl.
The stated hetaryl radicals preferably have 5-14 ring atoms, including 1-4 hetero atoms selected from the 1 p.
13 O.Z. 0050/43411 group consisting of N, 0 and S, are unsubstituted or substituted and are, for example, furyl, 2-furyl, 3furyl, thienyl, 2-thienyl, 3-thienyl, pyrrolyl, 1pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, isoxazolyl, 3isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, isothiazolyl, 3isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, pyrazolyl, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, oxazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, thiazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, imidazolyl, Iimidazolyl, 2-imidazolyl, 4-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-oxatriazolyl, pyridyl, 2-pyridyl, 3-pyridyl, 4pyridyl, pyridazinyl, 3-pyridazinyl, 4-pyridazinyl, pyrimidinyl, 2-pyrimidinyl, 4-pyrimidinyl, pyrazinyl, 2-pyrazinyl, 3-pyrazinyl, 1,2 ,4-trizInyl, 1,3,5-triazinyl or 1,2,4,5-tetrazinyl.
Adjacent substituents of the heteroaromatics may be condensed to form an aromatic or heteroaromatic ring, so that hetaryl also includes fused ring systems, eg.
benzofuranyl, isobenzofuranyl, 1-benzothienyl, 2-benzothienyl, indolyl, isoindolyl, benzisoxazolyl, benzoxazol, benzisothiazolyl, benzothiazolyl, 2-benzothiazolyl, 4benzothiazolyl, 5-benzothiazolyl, 6-benzothiazolyl, 7- 2* 5 benzothiazolyl, indazolyl, benzimidazolyl1, benzofuranyl, dibenz'ofuranyl, dibenzothienyl,, acridinyl, *phenanthridinyl, carbazolyl, quinolyl, isiquinolyl, phthalazinyl, quinazolinyl, quinoxalinyl, cinnolinyl, 1, 5-naphthyridinyl, 1, 6-naphthyridinyl, 1, 7-naphthyridinyl, 1, 8-naphthyridinyl, pteridinyl, pyrrolopyridinyl, pyrrolopyridazinyl, pyrrolopyriznidinyl, pyrrolopyrazinyl, pyrrolotriazinyl, furopyridinyl, furopyridazinyl, furopyrimidinyl, furopyrazinyl, furotriazinyl, thienopyridinyl, thienopyridazinyl, thienopyrimidinyl, thienopyraz inyl, thienotriazinyl, imidazopyridinyl, imidazopyridazinyl, imidazopyrimidinyl, imidazopyrazinyl, pyrazolopyridinyl, pyrazolopyridazinyl, pyrazolopyrimidinyl, 14 0. Z. 0050/43411 pyrazolopyrazinyl, isoxazolopyridinyl, isoxazolopyridazinyl, isoxazolopyrimidinyl, isoxazolopyrazinyl, oxazolopyridinyl, oxazolopyridazinyl, oxazolopyrimidinyl, oxazolopyrazinyl, thiazolopyridinyl, thiazolopyridazinyl, thiazolopyrimidinyl, thiazolopyrazinyl, isothiazolopyridinyl, isothiazolopyridazinyl, isothiazolopyrimidinyl, isothiazolopyrazinyl, triazolopyridinyl, triazolopyridazinyl, triazolopyrimidinyl or triazolopyrazinyl.
The stated heterocyclyl radicals preferably have 3-15 ring atoms, including 1-4 hetero atoms selected from the group consisting of N, 0 and S, are saturated or have parallel unsaturated bonds, are unsubstituted or substituted and aire, for example, 2-tetrc-hydrofuranyl, cxiranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3tetrahydrothienyl, z-pyrroiidinyl, 3-pyrrolidinyl, 3isoxazolidinyl, 4-isoxazolidinyl, 4-isothiazolidinyl, 3pyrazolidinyl., 4-pyrazolidinyl, 5-pyrazolidinyl, 2- **oxazolidiny., 4-oxazolidinyl, 5-oxazolidinyl, 2- 4thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2imidazcolidinyl, 4-imidazolidinyl, 1, 2,4-oxadiazolidin-3yl, 1,2 ,4-oxadiazolidin-5-yl, 1,2 ,4-thiadiazolidin-3-yl, l,2,4-thiadiazo.Lidin-5-yl, 1,2,4-triazolidin-3-yl, 1,3,4oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 1,3,4triazolidin-2-yl, 2, 3-dihydrofur-2-yl, 2, 3-dihydrofur-3yl, 2,5-dihydrofur-2-yl, 2,5-dihydrofur-3-yl, 2,3- V dihydro fur-3-yl, 2, 3-dihydrothien-2-yl, 2, 3-dihydrothien- 3-yl, 2, 5-dihydrothien-2-yl, 2, 5-dihydrothien-2-yl, 2,4pyrrolin-2-yl, 2,3-pyrrolin-3-yl, 2,5-pyrrolin-2-yl, pyrrolin-3-yl, 2, 3-isoxazolin-3-yl, 3,4-isoxazolin-3-yl, 4,5-isoxazolin-2-yl, 2,3-isoxazolin-4-yl, 3,4-isoxazoli- *4-yl, 4,5-isoxazolin-5-yl, 2,3-isothiazolin-3-yl, 3,4isothiazolin-3-yl, 4,5-isothiazolii-3-yl, 2,3isothiazolin-4-yl, 3,4-isothiazolin-4-yl, isOt-hiazolin-4-yl, 2,3-isothiazolin-5-yl, 3,4isothiazolin-5-yl, 4,5-isothiazolin-5-yl, 2,3dihyciropyrazol-3-yl, 2, 3-dihydropyrazol-4-yl, 2,3- 3,4-dihydropyrazol-1-yl, 3,4- 15 O.Z. 0050/4341.1 dihydropyrazol-2-yl, 3,4-dihydropyrazol-4-yi, 3,4- 4 ,5-dihydropyrazol-1-yl, dihydropyrazol-3-yl, 4 ,5-dihydropyrazol-4,-yl, 2, 3-dihydrooxazol-2-yl, 2, 3-dihydrooxazol-3-yl, 2, 3-dihydrooxazol-4-yl, 2, 3-dihydrooxazol- 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3 ,4-dihydrooxazol-4-yl, 3 ,4-dihydrooxazol-5-yl, 3,4dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-ciihydrooxazol-4-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 3-tetrahydropyridazinyl, 4-tetrahydropyridazinyl, 2tetrahydropyrimidinyl, 4-tetrahydropyrimidinyl, hydropyrimidinyl, 2-tetrahydropyrazinyl, 1,3, hydrotriazin-2-yl, 1,2 4 4-tetrahydrotriazin-3-yl, 1,3dihydrooxazin-2-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, 2-yl, 2H-1,4-benzothiazin-3-yl, 2H-1,4-benzoxazin-3-yl, 1, 3-dihydrooxazin-2-yl, 1, 3-dithidii-2-y1, N-morpholinyl or dihydroguinazolinyl.
Expressly included are -those heterocyclic radicals which carry further functional groups, for example oxo or thioxo groups, so that the heterocycly! radicals also include cyclic esters, thioeste:.:s or amides or thio analogs thereof, for example pyrrolidonyl, piperidonyl, 1-azacycloheptan-2-onyl, imidazolidinonyl, dikato- V piperazinyl or thiopyrrolidonyl.
The novel compounds cf~r be prepared, for eixample, by the following processes: For example, the phenol 1 (EP 251 082) can be reacted with the corresponding~ alkylating agents under alkaline conditions (for example, alkali metal carbonates in dipolar aprotic solvents, such as dimethylformamide, N-methylpyrrolidone, tetramethylurea, dimethylpropyleneurea, dimethylsulf oxide, sulfolane, etc.) to give the novel compounds 2 (Scheme 1) 16 O.Z. 0050/43411 Scheme 1 X Y B-0 X Y
OR
2 R1O2C HO X Y X Y X OR2 0 2
F
0 la lb :The hetarylation of the phenol 1 is known (EP 242 081) bu the alkylation of 1, in particular with unreac- S. tive alkylating agents, to give the ethers 2 presents 5 problems since the cyclization of 1 to la or lb is the only detectable reaction in some cases (Scheme This formation of byproducts can be suppressed if relatively highly concentrated solutions are employed to increase the reaction rate of the bimolecular reaction between the o" 10 phenol 1 and alkylating agent Hal-B (Hal Cl, Br or I) to give the active ingredients 2, and the reaction is carried out in the presence of catalytic amounts of iodine salts (eg. Nal or KI) in, for example, the abovementioned dipolar aprotic solvents in order to activate unreactive alkylating agents (Hal Cl or Br).
The active ingredients 2 are obtained in a similar manner by reacting the phenol 1 with alcohols under the conditions of the Mitsunobu reaction (Synthesis 1981, 1).
Furthermore, the phenylacetates 3 can be reacted 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 RIO2 R O OH RIO2 OR 2 2 O 3 4 2 Moreover, the ketoesters 5 can be subjected to a Wittig reaction with (C6H 5 3
P+-CH
2
-O-R
2 -Cl to give the novel compounds 2 (Scheme 3).
Scheme 3 Y X Y
B
RI0 2 C R'02 OR 2 The chemical literature describes many methods 10 for the synthesis of the a-ketoesters 5 (cf. for example L. Weinstock et al., Synthetic Communications 11 (1981), :943-946; J. March, Advanced Organic Chemistry, 3rd Edition (1985), J. Wiley Sons; R. Larock, Comprehensive Organic Transformations, 1st Edition 1989, VCH Publishers; M. Fieser, Reagents for Organic Synthesis, J. Wiley Sons); the synthesis of the ketoesters 5 starting from benzaldehyde 6 via a cyanohydrin route (EP 422 597), starting from ortho-haloaromatics 7 (Hal Cl, Br or I) via a Grignard route (EP 253 213) starting from benzoates 18 0. Z. 0050/43411 8 via a Punimerer rearrangement Amer. Chem. Soc. 1966, 5498; Synthesis 1982, 41) starting from acetophenones 9 via an oxidation/ es teri fication (Synthetic Communications 21 (1991), 2045; J. Prakt. Chem. 45 (1892), 377) or starting from benzoyl cyanides 10 (Tetrahedron Lett.
1980, 3539; Scheme 4) is mentioned here merely by way of example.
Scheme~ 4 x Y
CHO
2
C
*0
C
0* C
C*
C.
CC CC C C
CC..
S C p.
Y
x Y x Y NC'~ 'v Furthermore, the novel1 compounds 2 ars~ obtainable from the phenylacetates 3 via enamine formation to give 19 O.Z. 0050/43411 11, hydrolysis of the enamine to give the formyl derivative 4 (cf. Scheme 2) and alkylation of the formyl derivative (similarly to DE 40 25 892) (Scheme Scheme X Y N(Alkyl) 2 R'0 2
C
R10 2
C
OH
X Y ooooQ 0 *C *o oo o o oe oooo o ft
B
NO0
OR
2
RIO
2
C
2 Moreover, the enol ethers 2 can be prepared by eliminating an alcohol R 2 -OH from the acetals 12 Chem.
Soc. Chem. Commun. 1980, 838; Chem. Lett. (1976), 796) and can be obtained from the acrylates 13 by successive reaction with bromine, an alcoholate R 2 -O-M (M Li, Na, 10 K, Mg) and a protic acid, eg. NaHSO, Chem. Soc. 1958, 153) (similarly to EP 431 328; Scheme 6).
20 O.Z. 0050/43411 Scheme 6 X Y X Y X Y
SOR
2
OR
R'O
2 C OR 2
RIO
2 C/ RiO 2
C
12 2 13 Moreover, the propargyl ether 14 is a useful intermediate for the synthesis of the novel compounds and 16. For example, the reaction of 14 with aldehyde oximes R 10 -CH=NOH in the presence of NaOCl solution gives the isoxazole 15, and the reaction of 14 with aryl or hetaryl halides (Hal I or Br) in the presence of a Pd catalyst gives the acetylene 16 (Scheme 7).
Scheme 7 N' OR 10 OR Ar
Y
0R OR 2 10 The Examples which follow illustrate the preparation of the novel compounds.
EXAMPLE 1 Methyl (benzoylmethoxy) -phenyl) -B-methoxyacrylate (Table 3, No. 18) A mixture of 2.1 g (10 mmol) of methyl a-(2hydroxyphenyl)-B-methoxyacrylate (EP 251 082), 2.0 g mmol) of phenacyl bromide and 1.5 g (11 mmol) of K 2
CO
3 in ml of dimethylformamide is stirred overnight at room temperature. An additional 0.6 g of phenacyl bromide and 0.5 g of K 2
CO
3 are then added.
21 O.Z. 0050/43411 Stirring is carried out for 6 hours at room temperature the reaction mixture is diluted with water and the aqueous phase is extracted three times with methyl tert-butyl ether. The organic phase is dried over MgSO 4 and evaporated down. The residue is purified by column chromatography using hexane/ethyl acetate mixtures. 1.7 g of the title compound are obtained as a colorless solid (mp. 76 0
C).
1 H-NMR (CDCI 3 S in ppm): 7.95 broad, 2 H, aromatic); 7.5 4 H, 3 x aromatic, 1 x vinyl); 7.25 2 H, aromatic); 7.0 1 H, J 8 Hz, aromatic); 6,9 1 H, J 8 Hz, aromatic); 5.2 2 H, O-CH 2 3.8 3 H, O-CH a 3.65 3 H, O-CHa) EXAMPLE 2 Methyl *-phenylpyrrolidon-3-yl)-oxy)-phenyl)-Bmethoxyacrylate (Table 3, No. 16) a) 2-((N-Phenylpyrrolidon-3-yl)-oxy)-benzaldehyde 3.2 g (0.13 mol) of sodium hydride are added to 20 14.8 g (0.12 mol) of salicylaldehyde in 100 ml of dimethylformamide with gentle cooling. After evolution of gas has ceased, 29 g (0.12 mol) of 3-bromo-N-phenylpyrrolidone (prepared similarly to J. Med. Chem. (1987), 1995) are added and stirring is carried out overnight at room temperature. Thereafter, the reaction mixture is diluted with water and the aqueous phase is extracted three times with methyl tert-butyl ether. The combined organic phases are dried over MgSO 4 and evapora- S) ted down. The residue is purified by column chromatog- 30 raphy. 12.8 g of the title compound are obtained as a pale yellow solid.
'H-NMR (CDC13; 6 in ppm): 10.5 1 H, CHO); 7.0-8.0 9 H, aromatic); 5.15 (t, 1 H, J 8 Hz, O-CH); 3.9 2 H, N-CH 2 2.7 1 H, CHHB); 2.4 1 H, CHAH) b) Methyl 2-((N-Phenylpyrrolidon-3-yl)-oxy)-phenylglyoxylate 22 O.Z. 0050/43411 A mixture of 12.8 g (45 mmol) of the aldehyde from Example 2a in 100 ml of methylene chloride and 5 g (100 mmol) of sodium cyanide and 5 g (94 mmol) of ammonium chloride in 100 ml of water is 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 MgSO 4 and 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 is carried out overnight at room temperature and the reaction mixture is then evaporated down under reduced pressure.
The residue is taken up in 100 ml of water and heated at 100 0 C for 30 minutes, a viscous oil separating out. The water is decanted and the residue is taken up in methylene chloride. The organic phase is dried over MgSO, and evaporated down.
The residue is taken up in 100 ml of methylene chloride, and a solution of 0.3 g of KBr, 0.7 g of 20 NaH 2
PO
4
.H
2 0 and 0.9 g of Na 2
HPO
4 .2H 2 0 in 100 ml of water is added. 0.2 g of tetramethylpiperidine N-oxide is then added, followed by 40 ml of chlorine bleach (contains 12.5% of active C12) while stirring vigorously. Stirring is continued for 1 hour at room temperature, the aqueous phase is separated off, a further 40 ml of chlorine bleach are added and stirring is continued for a further hour. The organic phase is then separated off, extracted once with water, dried over MgSO, and evaporated down. The residue is purified by column chromatography. 6.4 g (42%) **30 of the title compound are obtained as a beige solid (mp. 110 0
C).
1 H-NMR (CDC13; 6 in ppm): 7.9 broad, 1 H, aromatic); 7.7 2 H, J 8 Hz, aromatic); 7.6 broad, 1 H, aromatic); 7.4 2 H, J 8 Hz, aromatic); 7.3 1 H, J 8 Hz, aromatic); 7- 7.25 2 H, aromatic); 5.15 1 H, J 8 Hz, O-CH); 1 H, N-CHHB); 3.85 1 H, N-CHHB); 3.85 3 I It 23 O.Z. 0050/43411 H, -0-CH 3 2.65 1 H, -CHjHB); 2.3 1 H, -CHAHB) c) Methyl a-(2-((N-phenylpyrrolidon-3-yl)-oxy)-phenyl)- J-methoxyacrylate (Table 3, No. 16) g (11 mmol) of methoxymethyltriphenylphosphonium chloride in 1 g (9 mmol) of potassium tertbutylate in 50 ml of tetrahydrofuran are stirred for minutes at room temperature. The mixture is then cooled to -20°C, 2 g (5.9 mmol) of the ketoester from Example 2b are added and the mixture is slowly allowed to warm up to room temperature. Stirring is continued for 2 hours at room temperature, the reaction mixture is diluted with water and the aqueous phase is extracted three times wi'h methyl tert-butyl ether. The combined organic phases are dried over MgSO 4 and evaporated down. The residue is purified by column chromatography using hexane/ethyl acetate mixtures. 1.4 g of the trans-isomer of the title compound are obtained as a pale yellow oil.
'H-NMR (CDC13; 6 in ppm): 7.7 broad, 1 H, aromatic); 7.5 1 H, vinyl); 6.9 :20 7.45 8 H, aromatic); 4.95 1 H, J 8 Hz, O-CH); 3.7 4.0 2 H, N-CH 2 3.8 3 H, O-CH 3 3.7 3 H, O-CH 3 2.45 1 H, -CHHB); 2.25 1 H, -CHjiH) V. EXAMPLE 3 Methyl a-(2-(3-(meta-methylphenyl)-prop-2-ynyloxy)phenyl)-B-methoxyacrylate (Table 3, No. 6) a) Methyl 2-(prop-2-ynyloxy)-phenylacetate 13 g (0.54 mol) of sodium hydride are added a little at a time to 75 g (0.45 mol) of methyl orthohydroxyphenylacetate in 500 ml of dimethylformamide.
Gentle cooling is 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. Stirring is carried out overnight at room temperature, after which the reaction mixture is diluted with 1 1 of water and the aqueous phase is extracted three times with methyl tertbutyl ether. The combined organic phases are dried over MgSO 4 and evaporated down. The residue is distilled.
I 24 O.Z. 0050/43411 71.6 g of the title compound are obtained as a pale yellow liquid (bp. (0.3 mbar.) 98-100°C).
1H-NMR (CDC13; 6 in ppm): 7.25 2 H, aromatic); 7.0 2 H, aromatic); 4.7 (d, 1 H, J about 1 Hz, O-CH 2 3.7 1 H, O-CH3), 3.65 (s, 2 H, CH 2 2.5 1 H, J about 1 Hz, =CH) b) Methyl a-(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 slow and then vigorous occurs. Once the evolution of gas has ceased, the reaction mixture is diluted with water and the aqueous phase is extracted twice with methyl tert-butyl ether. These organic phases are discarded. The aqueous phase is then acidified and is extracted three times with methyl tert-butyl ether.
The combined phases are filtered under suction with a silica gel and evaporated down.
.20 The residue is taken up in 200 ml of acetone, and 14 g (0.1 mol) of K 2
CO
3 and 11 g (0.09 mol) of dimethyl sulfate are added. Stirring is carried out for 4 hours at room temperature, after which the reaction mixture is evaporated down. The residue is taken up in methylene chloride. The organic phase is washed with dilute ammonia and water, dried over MgSO, and evaporated down. The residue is purified by column chromatography using hexane/ethyl acetate mixtures. 11 g of the transisomer of the title compound are obtained as a pale :30 yellow solid.
'H-NMR (CDCl 3 6 in ppm): 1 H, vinyl), 7.25 2 H, aromatic); 7.05 2 H, aromatic); 4.65 2 H, J about 1 Hz, 0-CH2); 3.8 3 H, O-CH 3 3.7 3 H, O-CH 3 2.5 1 H, J about 1 Hz, =CH) c) Methyl a-(2-(3-(meta-methylphenyl)-prop-2-ynyloxy)phenyl-B-methoxyacrylate (Table 3, No. 6) I
I_
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-iodotoluene, 2 g (20 mmol) of triethylamine, 0.3 g of triphenylphosphine, 20 mg of Cul and 60 mg of palladium(II) acetate in 20 ml of dimethylformamide is stirred for one hour at 70 0 C. Thereafter, the reaction mixture is diluted with water and the aqueous phase is extracted three times with methyl tert-butyl ether. The combined organic phases are dried over MgSO 4 and evaporated down. The residue is purified by col.umn chromatography using hexane/ethyl acetate mixtures. 0.9 g of the title compound is obtained as a crystalline solid (mp. 76"C).
'H-NMR (CDC1 3 6 in ppm): 1 H, vinyl); 6.9-7.4 8 H, aromatic); 4.9 (s, 2 H, O-CH 2 3.8 3 H, O-CH 3 3.7 3 H, O-CHF); 3 H, CH 3 EXAMPLE 4 Methyl a-(2-((3-para-methylphenyliosxazol-5-yl)-methoxy)phenyl)-B-methoxyacrylate (Table 3, No. 13) 20 50 ml of chlorine bleach (contains 12.5% of active C12) is added to a solution of 2 g (8.1 mmol) of the propargyl ether from Example 3 b and 1.7 g (12.5 mmol) of p-methylbenzaldehyde oxime in 30 ml of methylene chloride. Stirring is carried out for 30 minutes at room temperature, the phases are separated and the aqueous phase is extracted three times with methylene chloride.
The combined organic phases are extracted once with water, dried over MgSO 4 and evaporated down. The residue crystallizes and is stirred thoroughly with methyl tert- 30 butyl ether/hexane. 1.9 g of the trans-isomers of the title compound are obtained as a pale yellow solid (mp. 82°C).
H-NMR (CDCl 3 6 in ppm): 7.7 2 H, J 8 Hz, aromatic); 7.55 1 H, vinyl); 7.25 4 H, aromatic); 7.05 2 H, aromatic); 6.6 (s, 1 H, isoxazol); 5.2 2 H, O-CH 2 3.85 (s 3 H, O-CH 3 3.7 3 H, O-CH 3 2.4 3 H, CH 3 c 26 O.Z. 0050/43411 The compounds stated in the Tables below can be prepared in a similar manner.
ASF Aktiengesellsch~aft 900 05/31 920400 O.Z. 0050/43411 Table 1
H
3
CO
2
C
In Table 1, B may have the following meanings: x
CH
2 -C(=N-OCH 3 -a x III: M C. CC
C
C. C 4.e S C
S
IV:
x CH2-CH(-OCH O m x
-CH
2
-CH(-O-CH
2 -Cg~ x
-CH
2 -C(=O)-NWaO *BASF Aktiengesellschaft 920400 O.Z. 0050/43411 28 x VIII:
-CH
2
-C(=O)-N(CH
3 Qmar x VII:
CH
2 C(0)N(
HCH
3 )Ca
O
xx X: N m
I:
0 XII: NX 000
XIII:
l BASF &N~ktiengesellochaft 900 05/31 920400 O.Z. 0050/43411
XIV:
XV:
XVI:
XVII:
XVIIZ:
CH
2
CH
2
XIX:
it B3.SF Aktiengai~ellachaft 900 05/31 920400 O.Z. 0050/43411
XX:
XXI:
V
C
*CC.
XXII:
m
XXIII.:
H
CH
2
N,
0 BASF Aktiengesellschaft 900 ~.05/31 920400 O.Z. 0050/43411 In Table 1 the compounds given below have for example the following meanings: 1/1.2: 0 H
H
3
CO
2 CN.
H
I1/1.11: VII/l. 66 X/l. 160:
H
3
CO
2
C'
and XXII/l .66:
H
3
CO
2
C
'..I(BASF Aktiengesellschaft 900 05/31 920400 O.Z. 0050/43411 32 to XXIII) X, may have the fol- For each of the groups B (I lowing meaning Table 1
H
3
CO
2
C
10
H
3
S
5 5555
S
No. Xm 1 4-C -C 6
H
2 2-F 3 3-F 4 4-F 2, 4-F 2 6 2, 4, 6-F 3 7 23456F 8 2,3-F 2 9 2-Cl 10 3-Cl 11 4-Cl 12 2,3-Cl 2 13 2,4-Cl 2 14 2,5-Cl 2 2,6-Cl12 16 3 ,4-C12 17 3,5-C12 18 2,3,4-Cl 3 19 2,3,5-Cli 2,3,6-Cl 3 21 2,4,5-Cll 22 21,4,6-Cl 3 23 3,4,5-Cl 3 '1 BASF Aktiengesellscha~ft 900 05/31 920400 O.Z. 0050/43411 e No. Xm 24 2,3,4,6-C1 4 [2,3,5,6-C1 4 26 2,3,4,5,6-Cl 27 2-Br 28 3-Br 29 4-Br 2,4-Br 2 31 2,5-Br 2 32 2,6-Br 2 33 2,4,6-Br3 34 2,3,4,5,6-Br5 2-1 36 3-1 37 4-1 38 2,4-12 39 2-Cl, 3-F 2-Cl, 4-F 41 2-Cl, 42 2-Cl, 6-F 43 2-Cl, 3-Br 44 2-Cl, 4-Br 2-Cl, 46 2-Cl, 6-Br 47 2-Br, 3-Cl 48 2-Br, 4-Cl 49 2-Br, 50 2-Br, 3-F 51 2-Br, 4-F 52 2-Br, 53 2-Br, 6-F 54 2-F, 3-Cl 2-F, 4-Cl 56 2-F, 57 3-Cl, 4-F 58 3-Cl, 59 3-Cl, 4-Br 4 BASF Akctiengesellschaft 900 05/31 920400 O.Z. 0050/43411 S 0 tvw*6 No. Xm 3-Cl, 61 3-F, 4-Cl 62 3-F, 4-Br 63 3-Br, 4-Cl 64 3-Br, 4-F 2,6-Cl 2 4-Br 66 2-CH 3 67 3-CH 3 68 4-CH 3 69 2, 3- (CH 3 2 2, 4- (CH 3 2 71 2, 5- (CH 3 2 72 2, 6- (CH 3 2 73 3, 4- (CH 3 2 74 3, 5- (CH 3 2 2, 3 (CH 3 3 76 2, 3 (CH 3 3 77 2 ,3 (CH 3 3 78 2, 4,5- (CH 3 3 79 2 6- (CH 3 3 3, 4,5-(CI) 3 81 2 ,3, 4 6- (CH 3 4 82 2, 3, 5,6- (CH 3 4 83 2,3, 4, 5,6- (CH 3 84 2-C1-HS 85 3-C.-Hr 86 4-C 2
)H
87 2,4- (C 2
H-
5 2 88 2,6- (C 2
H
5 2 89 3 5- (C 2
H
5 2 2,4,6- (C 2 1 5 3 91 2-n-C.IH 7 92 3-n-C 3
H
7 93 1 4-ri-C 3
H
7 94J2--i-C 3
H-
7 3-i-C 3
H
7 I fit U
C
OC**
*U C C C~, BASF Aktiengesellschaft 900 920400 o.z. 0050/43411
SS
S.
S
S
No. Xm 96 4-i-C 3
H
7 97 2, 4- (i-C3117) 2 98 2, 6- (i-C 3 H7) 2 99 3 (i-C3H7) 2 100 2, 4,6- (i-C3H7) 3 101 2-S-C 4
H
9 102 3-S-C 4
H
9 103 4-S-C 4
H
9 104 2-t-C 4 H9 105 3-t-C 4 H9 106 4-t.-C 4 H9 107 2 (t-C 4 H9) 2 108 2, 4- (t-C 4
H
9 109 2, 5- (t-C 4
H
9 2 112 2,46- (t-C 4
H
9 113 4-n-C 9 Hj 9 115 4-n-C 1 5
H
3 1 116 4- 3-tetramethylbutyl) 117 4- 4-trimethyipropyl) 118 2-t-C 4 H9, 4-CH 3 119 2-t-C 4
H
9 5-CH 3 120 2, 6- (t-C4H9) 2, 4-CH3 121 2-CH3, 4-t-C 4 H9 122 2-CH 3 6-t-C 4
H
9 123 2-CH-i, 4-i-C3H 7 124 2-CH 3 5-i-CIH 7 125 3-CH 3 4-i-C 3
H
7 126 2-i-C 3
H
7 5-CH- 3 127 2,4-(t-C 4
H
9 2 6-i-C.IH 7 18 2-allyl 129 3-allyl 130 4-allyl 131 2-allyl, 6-CHj 0 ~BASF Aktiengesellslchaft 900 05/31 920400 O.Z. 0050/43411 Ve No. X, 132 2-c~Yc1o-C6H11 133 3-CYClo-C6Hil 134 4-cyclO-C6II 135 2,4-(CYCl-C6Hll)2, 6-CH3.
136 2-C-I, 4-CYC1o-C6HII 137 2-CH 2
-C
6
H
138 3-CH 2
-C
6
H
139 4-CH- 2
-C
6
H
140 2-CH 2
-C
6
H
5 4-CH 3 141 2-CH 3 4-CH 2
-C
6
H
143 3CH 145 4- (2-i-C 3
H-
7
-C
6
H
4 146 4-C 6
H
5 2,6-(CH3)2 147 2-C1, 4-C 6
H-I
148 2-Br, 4-C 6
H
149 2-CbH 5 4-C1 150 2-C 6
H
5 4-Br 151 2-CH 2
C
6
H
5 4-C1 152 2-CH 2
C
6 H_ 4-B'r 153 2-Cl, 4-CH- 2
C
6 '154 2-Br, 4-CH 2
C
6 Hr, 155 2-CYClo-C6H11i, 4-Cl 156 2-CYClo-C6H 1 1, 4-Br 157 2-Cl, 4-CYCIO-C6H1I 158 2-Br, 4-CYC10-C 6 Hjj 159 2-OCH- 3 160 3-OCH- 3 161 4-0CM 3 162 2-0C 2
H
163 3-0-C 2
H
164 4-0-C 2
H
165 166 3-0-n-C-;H 7 167 4-0-n-C 3
H
7 .11 J. BASF Aktiengesellschaft 900 05/31 920400 O.Z. 0050/43411 No. X 168 2-O-i-C 3 H7 169 3-O-i- 3 H7 170 4-O-i-C 3 1 7 171 2-O-n- 6
H
1 3 172 3'-O-n-C 6
H
1 3 173 4-O-n-C 6
H
1 3 174 2-O-n-CBH 1 7 175 3-O-n-C 8 H1 7 176 4-O-n-C 8
H
1 7 177 2-O-H 2 6
H-
178 3-O-CH 2
C
6
H
179 4-O-CH 2
C
6
H
180 2-0- (CH 2 3 0 6
H
5 181 3-0- (CH 2 3
C
6 Hr, 182 4-0- (OH 2 306H-5 183 2, 4- (OCH 3 2 184 2-CF 3 185 3-CF 3 186 4-CF 3 187 188 189 4-OCF3 190 3-OCH 2
CHF
2 191 2-NO 2 192 3-NO 2 193 4-NO 2 194 2-ON 195 3-ON 196 4-ON 197 2-CHI, 3-Cl 198 2-OH 3 4-Cl 199 2-OH 3 5-01 200 2-CH3, 6-01 201 2-CHI, 3-F 202 2-OH 3 4-F 2 03 2-OH 3 m "I BASF Aktiengesellschaft 900 05/31 920400 O.Z. 0050/43411 00..
.00.
0 00 No. }Xm 204 }2-CH 3 6-F 205 12--CH 3 3-Br 206 2-CH 3 4-Br 207 2-Gil 3 208 2-C-I> 6-Br 209 2-Cl, 3-CH 3 210 2-C1, 4-CH 3 211 2-Cl, 5-CH 3 212 2-F, 3-CH 3 213 2-F, 4-CH 3 214 2-F, 5-CH 3 215 2-Br, 3-CH 3 216 2-Br, 4-CH 3 217 2-Br, 5-C- 3 218 3-C- 3 4-Cl 219 3-CR 3 220 3-CH 3 4-F 221 3-CR 3 222 3-CH 3 4-Br 223 3-CH 3 224 3-F, 4-CH 3 225 3-Cl, 4-CH 3 226 3-Br, 4-CH 3 227 2-Cl, 4, 5- (CH 3 2 228 2-Br, 4, 5- (CH 3 2 229 2-Cl, 3, 5- (CH 3 2 230 2-Br, 3, 5- (Cl)2 231 2, 6-Cl 2 4-CR 3 32 2,6-F 2 4-CH 3 233 2,6-Br 2 4-CR 3 234 2,4-Br- 2 6-CR 3 235 2,4-F 2 6-CH 3 23 6 2,4-Br 2 6-CH 3 237 2, 6- (C-I 3 4-F 238 2, 6- (CH) 2, 4-Cl 239 12,6-CRI):, 4-Br 11 BASF Aktiengesellschaft 900 05/31 920400 O.Z. 0050/43411 No.
H
240 3, 5- (CH4) 2 4-F 241 3, 5- (CI) 2 4-Cl 242 3, 5- (CH3 4-Br 243 2, 3,6- (CH3)3, 4-F 244 2, 3,6- (CHj) 3 4-Cl 245 2, 3,6- (CH 3 3 4-Br 246 2, 4- (CH 3 6-F 247 2, 4- (CHI), 6-Cl 248 2, 4- (CHi-) 2 6-Br 249 2-i-C 3
H
7 4-Cl, 5-CH 3 250 2-Cl, 4-NO 2 251 2-NO2, 4-Cl 252 2-OCH 3 5-NO 2 253 2,4-Cl 2 5-NO 2 254 2,4-Cl 2 6-NO 2 255 2,6-Cl 2 4-NOn) 256 2,6-Br 2 4-NO 2 257 2,6-J 2 4-NO 2 258 2-CH 3 5-i-C3H- 7 4-Cl 259 2-CO 2
CH-
3 260 3-CO 2
CH
3 261 4-CO-CH- 3 262 2-CC_(C 2
H
5 263 3-CO 2
,(C
2
H
5 264 4-CO2 (C 2 265 2-CO:: (n-CIH 7 266 3-C02)(n-C 3
H
7 267 4-CO- (n-C 3 7 268 2-CO2(i-C3H 7 269 3-C0 2 (i-C 3
H
7 270 4-C0 2 (i-C1-1 7 271 2-CO2 (n-C 6
H
1 3 272 3-CO 2
(T-C
6
H
1 -f) t273 4-CO 2 1(n-C 6 H-yI) 274 2-CHn-OC~i- 275 13-CH 2
-OCHI
tr BASF Aktiengesellschaft 900 05/31 920400 O.Z. 0050/43411
S.
S
No.
XM
276 4-CH- 2 -OCH3 277 2-CH 2 O(C2Hs) 278 3-CH 2 279 4-CH- 2 0(C2H5) 280 2-CH 2 0 (n-C 3
H
7 281 3-CH 2 0 (n-C 3
H
7 282 4-CH 2 O(n-C 3 H-7) 283 2-CH-{ 2 (i-C3H 7 284 3-CH 2 0O(i-C 3
H
7 285 4-CH 2 0O(i-C3H 7 286 2-CHO 287 3-C-b 288 4-CHO 289 2-CO-CH3 290 3-CO-CH- 3 291 4-CO-CH 3 292 2-CO-CH 2
-CH
3 293 3-CO-CH 2
-CH
3 294 4-CO-CH 2
-CH
3 295 2-CO-CH- 2
-CH,,-CH
3 296 3-CO-CH 2
-CH
2 -CH3 297 4-CO-CH 2
-CH
2
-CH-I
298 2-CO-CH (CH3) -CH3 299 3-CO-CH (CH3) -CH3 300 4-CO-C-I(CH 3
-CH
3 301 2-Me-4-CHO 302 2-Me-4-CH 3
-CO
303 2-Me-4-C- 3
-CH
2
-CO
304 2-Me-4-CH 3
-CH
2
I-CH
2
-CO
305 2-Me-4-CH-3-CH(CH 3
)-CO
306 2,5-Me 2 -4-CHO 307 2, 5-Me 2 -4-CH 3
-CO
308 2, 5-Me 2 -4-CH--CH 2
-C-CO
310 2, 5-Me 2 -4-CH3-CH 2
-CH
2
)-CO
311 2-Cl-4-CHO It ASF Aktiengesellschaft 920400 OZ.00/31 O.Z. 0050/43411 S* 312 2-Cl-4-CH3-CO 313 2-Cl-4-CH 3
-CH
2
-CO
314 2-C1-4-CH 3 -CH (CH3) -CO 315 2,5-C1 2 -4-CHO 316 2, 5-C1 2 -4-CH 3
-CO
317 2, 5-C1 2 -4-CH 3
-CH
2
-CO
318 2, 5-C1 2 -4-CH 3
-CH
2
-CH
2
-CO
319 2, 5-C1 2 -4-CH 3
CH(CH
3
)-CO
320 2-C(=NOCH- 3 )-CH3 321 3-C (=NOCH 3
-CH
3 322 4-C (=NOCH 3 -CHi 323 2-C (=NOC 2
H
5
-CH
3 324 3-C (=NOC 2
H
5
-CH
3 325 4-C (=NOC 2
H
5
-CH
3 326 2-C (=NO-n-C 3
H
7
-CH
3 327 3-C (=NO-n-C 3
H
7
-CH-
3 328 4-C (=NO-n-C 3 H7) -CH 3 329 2-C (=NO-i-C 3
H
7
-CH
3 330 3-C (=NO-i-C 3
H
7
-CH
3 331 4-C (=NO-i-C 3 H7) -CH 3 332 2-C (=NO-allyl) -CH3 333 3-C(=NO-a1ly1)-CH3 334 4-C(=NO-allyl)-CH3 335 2-C (=NO-trans-chloroallyl) -CH3 336 3-C (=NO-trans-chloroa11y1) -CH3 337 4-C C=NO-trans-chloroally1) -CH3 338 2-C (=NO-propargyl) -CH3 339 3-C (=NO-propargy1) -CH 3 340 4-C (=NO-propargyl) -C- 3 341 2-C (=NO-n-C 4
H-
9
-CH
3 342 3-C (=NO-n-C 4 H9) -CH 3 343 4-C (=NO-n-C 4 Hj) -CH.1 344 2-C (=NO-CHZ-C 6 Hr,) -CH 3 345 3-C (=NO-C- 2
-C
6
H
5
-CH
3 346 4-C (=NO-CH 2 -CHS,) -CH 3 347 2-CH-i-4-CH=NOCH3 1 t BASF A~ktiengesellochiaft 920400 42 o.Z. 0050/43411 a a a. a No. Xm 348 2-CHi-4-CH=NOC 2 349 2-CH 3 4-CH=NO-n-C 3 H7 350 2-CH 3 -4-CH=NO-i-C3H7 351 2-CH 3 4-CH=NO-allyl 352 2-CH3-4-CH=NO- (trans-chioroallyl) 353 2-CH 3 -4-CH=No-propargyl 354 2-CH 3 -4-CH=NO-n-C 4
H
9 355 2-CH 3 -4-CH=NO-CH 2 356 2-CH-i-4- (CHj-C=NOCH 3 357 2-CH 3
(CH
3
-C=NOC
2
H
5 358 2-CH.
3
(CH
3 -C=NO-n-C 3
H
7 359 2-CH, 3
(CH
3 -C=NO-i-C 3
H
7 360 2-CH 3
(CH
3 -C=NO-allyl) 361 2-CH 3
(CH
3 -C=NO-trans-chloroallyl) 362 2-CH 3
(CH
3 -C=NO-propargyl) 363 2-CH 3
(CH
3 -C=NO-n-C 4 H9i) 364 2-CH3I-4- (CH 3
-C=NO-CH
2 -C6H 5 365 2-CH 3
(C
2
H
5
-C=NO-CH
3 366 2-CH 3 4- (C 2
H
5
-C=NO-C
2
H
5 367 12-CH-4- (C 2
H
5 -C=NO-n-C 3
H
7 368 2-CH 3 4- (C 2
H
5 -C=NO-i-CIH- 7 369 2-CH-3-4- (C 2
H
5 -C=NO-allyl) 370 2-CH3-4- (C 2
H
5 -C=NO-trans-chloroallyl) 371 2-CHj--4- (C 2 Hr-C=NO-propargyl) 372 2-CH3-4- (C 2
H
5 -C=NO-fl-C4H 9 373 2-CHW-4- (C2HW-C=NO-CH2,-CcH 374 2, 5- (Cl- 3 2 -4 -(CH 3 -C=NOCH31) 375 2, 5- (Cl- 3 2
(C
3
-C=NOC
2 H-{j 376 2, 5- (CH3) 2-4- (CH 3 -C=NO-n-C 3 H7) 377 2, 5- (CI) 2-4- (CH 3 -C=NO-i-C 3 H7) 378 2, (CHi-C=NO-a11yl) 379 2, 5- (CH- 3 2 (CH--C=NO-transchloroal1y1) 380 2, 5- (CHI) 2-4- (CH-C=NO-propary1) 381 2, 5- (CH 3 2 (CH-j-C=NO-n-C 4 H9) 382 12, 5- (CI ,4 C.-=OC CH 383 2-C~c, A, I It BASF Aktiengesellschaft 920400 920400 O.Z. 0050/43411
II
S.
S
0000 No. X 384 3-C6H5 385 C(H 386 2-(2'-F-C6H4) 387 2- (3 '-F-C 6 14) 388 2- (4 '-F-C 6
H
4 389 3- (2 '-F-C 6
H
4 390 3- (3 '-F-C 6
H
4 391 3- (4 '-F-C 6
H
4 392 4- (2 '-F-C 6
H
4 393 4- (3 '-F-C 6
H
4 394 4- (4 '-F-C 6
H
4 395 2- (2 '-Cl-C 6
H
4 396 2- (3 '-C1-C 6 1 4 397 2- (4 '-Cl-C6H 4 398 3- (2 '-C-C 6
H
4 399 3- (3 '-Cl-C 6
H
4 400 3- (4 6
H
4 401 4- (2 '-C1-C 6
H
4 402 4- (3 '-Cl-C 6
H
4 403 4- (4 '-Cl-'C 6
H
4 405 2- (2 '-CH 3
-C
6
H
4 406 2- (3 '-CH 3
-C
6
H
4 407 (4 '-CH- 3
-C
6 H4) 408 3- (2 '-CH 3
-C
6
H
4 409 3- (3 '-CH 3
-C
6
H
4 410 3- (4'-CH- 3 -C6H4) 411 4- (2 '-CH 3 -C6H 4 412 4- (3 '-CH 3
-C
6
H
4 413 4- (4 '--CH 3
-C
6
H
4 414 2- (2 '-CH 3
-CO-C
6
H
4 415 2- (3 '-CH 3
-CO-C
6
H-
4 416 2- (4 '-CH- 3
-CO-C
6
H
4 417 3- -CH 3
-CO-C
6
H
4 418 3- (3 '-CH 3
-CO-C
6
H
4 419 3- (4 '-CH 3
CO-C
6
H
4 420 14- (2 '-CHv-CO-C(-i4) It BRSF Akttiengesellsch~aft 900 05/31 920400 O.Z. OnSO/43411 C 6*
C
5* 6 t S C *5 5 9
S
.5.5
S
SC s
C.
.9*S
C
55..
No. X, 421 4- (3 '-CHj-C(D-C 6
H
4 422 4- (4 '-CH- 3
-CD-C
6
H
4 423 2- (2'-(CH 3 -'C(=NOallyl) )-C 6
H
4 424 2- (=NOallyl) -C6H4) 425 2- (4'-(CH 3 -C (=NOallyl))-C6H4) 426 3- (2'-(CH 3 -C (=NOallyi) )-C 6
H
4 427 3- (3'-(CY 3 -C (=NOaJlyl))-C 6
H
4 4- 3- (4'(CH 3 -C (=NOallyj) -C 6
H
4 429 4- (2'-(CH3-C (=Noallyl) )-C 6
H
4 430 4- (=NOalyl) -C6H-4) 431 4-(4W- (CH 3 -C (=NOallyl))-C6H4) 432 2- (2'--CH 3
O
2
C-C
6
H
4 433 2- (3 '-CH 3
O
2
C-C
6
H
4 434 2- k4 '-CH 3 2
C-C
6 435 3- (2 '-CH 3
O
2
C-C
6
H
4 436 3- (3 '-CH 3
O
2
C-C
6 4 437 (4'-CI- 3 0 2
C-C
6
H
4 438 4- -CH 3
O
2
C-C
6
H
4 439 4- (3 '-CH 3
O
2
C-C
6
H
4 440 14- (4'-CH 3
O
2
C-C
6
H
4 441 2- (2 '-CH- 3 0-C 6
H
4 442 2- (3 '-CH- 3 0-C 6
H
4 443 2- (4'-CH 3
O-C
6
H
4 444 3- (2'-C-hO-C6H 4 445 3- (3 '-CH 3
O-C
6
H
4 446 3- (4 '-CH 3 0-C 6
H
4 447 4- (2 '-CH 3
O-C
6
H
4 448 4- (3 '-CH 3
O-C
6
H
4 449 4- (4 '-CH 3
O-C
6
H
4 450 '-0 2
N-C
6
H
4 451 2- (3'-0 2
N-C
6
H
4 452 2- (4 '-0 2
N-C
6
H
4 453 3- (2 '-0 2
N-C
6
H
4 454 3- (3 '-0 2
N-C
6
H
4 455 3-(4 '0,:N-CbH4) 456 4- (2'b-O-N-C6H 4 1 BASF Aktiengoel11chaft 900 05/31 920400 O.Z. 0050/43411 No. Xm 457 4- (3 '-0 2
N-C
6 H4) 458 4- (4 '-0 2
N-C
6
H
4 459 2- (2 1-NC-C 6 H4) 460 2- (3'-NC-C6H 4 461 2- (4'-NC-C6H 4 462 3- (2 '-NC-C 6
H
4 463 3- (3 '-NC-C 6
H
4 464 3- (4'--NC-C 6
H
4 465 4- (2'-NC-C 6
H
4 466 4- (3'-NC-C 6
H
4 467 4- (4'-NC-C 6
H
4 468 2- (2 '-CF 3
-C
6
H
4 469 2-(3 '-CFI-C 6
H
4 470 2- (4'-CFI-C 6
H
4 471 3- (2 '-CF-i-C6H 4 472 3- (3 '-CF 3
-C
6
H
4 .11, 3 (4'-CF 3 -c6H4) 474 4- (2 '-CF 3
-C
6
H
4 475 4- (3 '-CF 3
-C
6
H
4 476 4- (4 '-CF 3
-C
6
H
4 477 2-O-C 6
H
475 3-O-C 6 476 4-O-C 6
H-
478 2-O-(2'-F-C6H4) 479 2-0- (3 '-F-C 6
H
4 480 2-0- (4'-F-C 6
H
4 481 3-0- (2 '-F-C 6
H
4 482 3-0- (3 '-F-C 6
H
4 483 3-0- (4'-F-C 6
H
4 484 4-0- (2'-F-C 6
H
4 485 4-0- (3'-F-C6H- 4 486 4-0- (4'-F-C 6
H
4 487 2-0- (2 '-C1-C 6
H
4 488 2-0-(3 '-Cl-C 6
H
4 489 2-0- (4 '-Cl-CrH 4 490 (2 1 -Cl-C-.H 4 le BASF iktionoesellachaft 900 05/31 920400 O.Z. 0050/43411 No. 491 3-0- (3 '-C-C 6
H
4 492 3-0- (4'-Cl-C 6
H
4 493 3-0- (4'-Cl-C 6 H4) 494 4-0- (2 '-Cl-C 6
H
4 495 4-0- (3 '-C1-C 6
H
4 496 4-0- (4 '-Cl-C 6
H
4 497 2-0- (2'-CH 3
-C
6
H
4 498 2-0- (3 '-CH3I-C 6
H
4 499 2-0- (4 '-CH 3
-C
6
H
4 500 3-0- (2 '-CH 3
-C
6
H
4 501 3-0- (3 6
H
4 502 '-CH 3
C
6
H
4 503 4-0- (2 '-CH 3
-C
6
H
4 504 4-0- (3 '-CH 3
-C
6
H
4 505 4-0- -CH 3
-C
6
H
4 506 2-0- (2 '-CH 3
-CO-C
6
H
4 507 2-0- (3 '-CH 3
-CO-C
6
H
4 508 2-0- (4 '-CH 3 -C0-C 6
H
4 509 3-0- (2 '-CH 3 -C0-C 6
H
4 510 3-0- (3 '-CH 3
-CO-C
6
H
4 511 3 (4 -CH 3 -C0-C 6H 4 512 4-0- (2 '-CH 3 -C0-C 6
H
4 513 4-0- (3 '-CH- 3 -C0-C 6 -iA) 514 4-0- (4'-CH 3 -CO-C6H 4 515 2-0- (2-(CH3-C (=N~allyl) -C 6
H
4 516 (3'(CH3-C (=N~allyl) -6H4) 517 2-0- (4-(CH 3 -C (=NOallyl) -C 6 11 4 518 3-0- (2-(CH3-C (=NOallyl) -C 6
H
4 519 3-0- (2-(CH- 3 -C (=lallyl) -C 6
H-
4 520 3-0-1 -(CH3-C (=Noal1y1) )-C 6
H
4 521 4-0-(2'-(CH3-C(=N~al1yl) )-C 6
H
4 522 4-0- (3-(CH 3 -C (=NOallyl) )-C 6
H
4 523 4-0-C(4'(CHI-C (=N~a11y1) )-C 6
H
4 524 2-0- (2 '-CH.10C-C 6
H
4 525 2-0- (3 '-C-I 3 0;-'C-C 6
H
4 526 2-0- (4 '-C~i-h0C-C 6
H
4 BASF Aktiengesellschaft 900 05/31 920400 O.Z. 0050/43411 No. Xm 527 3-0- (2 '-CH 3
O
2
C-C
6
H
4 528 3-0- (3 '-CH 3 0 2
C-C
6
H-
4 529 3-0- (4 '-CH 3
O
2
C-C
6
H
4 530 4-0- (2 '-CH 3 0, 2
C-C
6
H
4 531 4-0- (3 '-CH 3 0 2
C-C
6
H
4 532 4-0- (4 '-CH 3 0 2
'C-C
6
H
4 533 2-0- (2 '-CH 3 0-C 6
H
4 534 2-0- -CH 3 O-C6H 4 535 2-0- (4 '-CH 3
O-C
6
H
4 536 3-0- (2 '-CH 3
O-C
6
H
4 537 3-0- (3 3 0-COW 4 538 3-0- (4'-CH 3
O-C
6
H
4 539 4-0- (2 '-CH 3 0-C 6
H
4 540 4-0- (3'-CH 3
O-C
6
H
4 541 4-0- (4 '-CH 3
O-C
6
H
4 542 2-0- -0 2
N-C
6
H
4 543 2-0- (3 '-0 2
N-C
6
H
4 544 2-0- (4'-0 2
N-C
6
H
4 545 3-0- (2'-0 2
N-C
6
H
4 546 3-0- (3 '-0 2
N-C
6
H
4 547 3-0-1(4'-0 2
N-C
6
H
4 548 4-0- (2'-02N-C6H 4 549 4-0- (3 '-0 2
N-C
6
H
4 550 4-0- (4'-0 2
N-C
6
H
4 551 2-0- -NC-C6I- 4 552 2-0- (3'-NC-C 6
H
4 553 2-0- (4'-NC-C 6
H
4 554 3-0- (2 '-NC-C 6
H
4 555 3-0- (3'-NCC 6
H
4 556 3-0- (4'-NC-C 6
H
4 557 4-0- (2 '-NC-C 6
H-
4 558 4-0- (3'-NC-C 6
H
4 559 4-0-(4'-NC _C 6
H
4 560 2-0- (2 '-CF 3
-C
6
H
4 561 2-0- (3 '-CFI-C 6
H
4 562 12-0- (4 '-CF 3
-C
6
H
4 t BASF Aktiengesellschaft 900 05/31 920400 o.Z. 0050/43411 'No. x 563 3-0- (2 '-CF 3
-C
6 H4) 564 3-0-(3 '-CF 3 -C6H 4 565 3-0- (4'-CF 3
-C
6
H
4 566 4-0- (2 '-CF 3
-C
6
H
4 567 4-0- (3 '-CF 3
-C
6
H
4 568 4-0- (4 '-CF 3 1-C 6
H
4 569 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-pyridinyl-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-pyrirnidinyl-3' 586 4-pyrimidinyl-4' 587 2-pyzazolyl-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
S.
S No. Xm 599 3-iloxazolyl-3' 600 3-iqoxazolyl-4' 601 602 4-i~oxazolyl-J' 603 4-isoxazolyl-4' 604 605 12-isothiazolyl-31 606 2-isothiazolyl.-4' 607 608 3-isothiazolyl-3' 609 3-isothiazolyl-40 610 61. :4-isothiazolyl-3' 62.2 4-isothiazolyl-4' 613 614 2-iinidazolyl-1' 615 2-imidazolyl-2' 616 2-imidlazol.yl-4' 617 3-imidazolyl-1' 618 3-imidazolyl-2' 619 3-imidazolyl-4' 620 4-iznidazolyl-1' 621 4-imnidazolyl-21 622 4-imidazolyl-4' 623 2-oxazolyl-2' 624 2-oxazolyl-4' 625 626 3-oxazolyl-2' 627 3-oxazolyl-41 628 3-oxazolyl-S, 629 4-oxazolyl-21 630 4-oxazolyl-4' 631 4-oxazolyl-51 632 2-thiazolyl-2' 633 2-thiazoly1-4' 634 00 A1A, tI BASF Aktiengeaellachaft 900 05/31 920400 O.Z. 0050/43411 No. X, 635 3-thiazolyl-2' 636 3-thiazolyl-4' 637 638 4-thiazolyl-2' 639 4-thiazolyl-4' 640
S
SS
S S BJ ShF A1ktiengeuelluchaft 900 05/31 920400 O.Z. 0050/43411 Table 2
H
3
CO
2
C
10
CH
3
S
S
S
S
No. A 1 pyrrolyl-3 2 N-CH 3 -pyrrolyl-3 3 N-C 6
H
5 -pyrrolyl-3 4 N- (4 '-CH 3
-C
6
H
4 -pyrrolyl-3 N- (3 '-CH 3
-C
6
H-
4 -pyrrolyl-3 6 N- (2 '-CH 3
-C
6
H
4 -pyrrolyl-3 7 N- (4 '-CH3O-C 6
H
4 -pyrrolyl-3 8 N- (3 '-CH 3
O-C
6
H
4 -pyrrolyl-3 9 N- (2 '-CH3O-C 6
H
4 -pyrrolyl-3 N- (4 '-N0 2
-C
6
H
4 -pyrrolyl-3 11 N- (3'-N2-C 6
H
4 -pyrrolyl-3 12 N- (2 '-N 2
-C
6
H
4 -pyrrolyl-3 13 N- (4'-CN-C 6
H
4 -pyrrolyl-3 14 N- (3 1 -CN-C 6
H
4 -pyrrolyl-3 15 N- (2 '-CN-C 6
H
4 -pyrrolyl-3 16 N- (4 '-C1-C6H 4 -pyrrolyl-3 17 N- (3 '-C1-C 6
H
4 -pyrrolyl-3 18 N- (2 '-C1-C 6
H
4 -pyrrolyl-3 19 pyrrolyl-2 N-CH -pyrrolyl-2 21 N-CtH-pyrroly1-2 22 N- 4 -CH t-CbH 4 -pyrroly1-2 23 N- i-C 6
H
4 -pyrrolyl-2 24 N- (2 '-CH j-C 6
H
4 -pyrrolyl-2 IN- (4 '-CiO-C 6
H-
4 -pyrrolyl-2 BASF Akctiengesellschaft 900 .05 31 920400 O.Z. 005L,43411 No. A 26 N- (3 '-CH- 3 0-C 6 H4) -pyrrolyl-2 27 N- (2 '-CH 3
O-C
6 H4 -pyrrolyl-2 28 N- (4 '-N0 2
,-C
6
H
4 -pyrrolyl-2 29 N- (3 '-NO -C6H 4 -pyrrolyl-2 N- (2 '-N-C 6
H-
4 -pyrrolyl-2 32 N- (4 '-CN-C 6
H
4 -pyrrolyl-2 32 N- (3 '-CN-C 6
H
4 -pyrrolyl-2 33 N- (2 '-CN-C 6
H
4 -pyrrolyl-2 34 N- (4 '-Cl-C 6
H
4 -pyrrolyl-2 N- (3 '-Cl-C 6
H
4 -pyrrolyl-2 37 N (uyl2 C1CH)yrll 37 5u-2-uy- 38 5-C6H5-furyl-2 39 5-(4-IC 6 H 4)fry -fry- 5- (4'1 -CIH3-C 6
H
4 -f uryl-2 41 5- (3 '-CHI-C 6
H
4 -f uryl-2 42 5- (2 '-CH3-C 6 4 -furyl-2 43 5- (4 '-CH 3
O-C
6
H
4 -f uryl-2 44 5- 3 0-C 6
H
4 -furyl-2 5- (2'-CI-1-C 6
H
4 uryl-2 47 5- (4 '-N0 2
-C
6
H
4 -furyl-2 47 5- (3 '-NO 2 -C6H 4 -furyl-2 48 5- (2'-N-C 6 1- 4 -f uryl-2 49 5- (34'-CN-C 6
H
4 -f uryl-2 5- (3 '-CN-C 6
H
4 -furyl-2 52 5- -CN-C 6
H
4 -f uryl-2 52 5- (4'-Cl-C 6
H
4 -furyl.-2 53 5- (3 '-Cl-C 6
H
4 -f uryl-2 54 5 (-C-C 6
H
4 uy- 4-CrH5-f uryl-2 56 4 -C(4 -CH 5 -C6ry-fry 57 4- (4 '-CHI-C 6
H-
4 -f uryl-2 58 4- (3'-CH-j-C 6
H
4 -f ury1-2 59 4- (2 '-CH3-C 6
H
4 -f uryl-2 4- (4 '-CH iO-CPH 4 -furyl-2 0.
00 0000 ol BASF' 2Utngeaellachaft 900 05/31 920400 O.Z. 0050/43411 No. A 62 4- (2 '-CH 3 C6-4 -furyl-2 63 4- (4 '-N02,-CEH4) -furyl-2 64 4- (3 '-NO 2 -C6H4 -furyl-2 4- (2 '-N0 2
,-C
6
H
4 -f uryl-2 66 4 (4 '-CN-C 6
H
4 -f uryl-2 67 4- (3 :I\N- 6
H
4 -furyl-2 68 4 (2 '-,CN-C 6
H
4 furyl1-2 69 4- (4 '-Cl-C 6
H
4 -f uryl-2 4- (3 1 -C 6
H
4 -f uryl-2 71 4- (2 '-C1-C 6
H
4 -f uryl-2 72 thienyl-2 73 5-CH 3 -thienyl-2 74 5-C,H5-thienyl-2 5- (4'-CH3-C 6
H
4 -thienyl-2 76 5- (3 '-CH-1-C 6
H
4 -thienyl-2 77 5- (2 '-CH 3
-C
6
H
4 -thienyl-2 78 5- -CH 1 0-C 6
H-
4 -thienyl-2 79 5- (3 '-CHIO-C 6
H-
4 -thienyl-2 5- (2 '-CH 3 O-C6H4 -thienyl-2 81 5- (4 '-N0 2
-C
6
H
4 -thienyl-2 82 5- (3 '-NO-2-C 6
H
4 -thienyl-2 83 5- -N0 2
_-C
6
H
4 -thienyl-2 84 5- (4'-CN-CbH4) -thienyl-2 5- (3'-CN-C 6
H
4 -th-ienyl-2 86 5- (2 '-CN-C 6
H
4 -thienyl-2 87 5-(4 '-C1-C 6
H
4 -thienyl-2 88 5- (3 C1-C 6
H-
4 -thienyl-2 89 5- (2 '-Cl-C 6
H
4 -thienyl-2 90 4-CH 3 -thienyl-2 91 4-CbHr,thienyl-2 92 4- (4 '-CI-b-C 6
H
4 -thienyl-2 93 4- (3'1 -CH 3
-C
6
H
4 -thienyl-2 94 4- (2 '-CHI-C 6
H
4 -thienyl-2 4-4 W-CI-{1-C 6
H-
4 -thienyl-2 96 4- (3 '-CH tO-C 6
H
4 -thienyl-2 97 4- (2 '-CHIO-C6H 4 -thienyl-2
S
55 S S
S
S
S S S BASF Aktiengesellschaft 920400 O.z. 0050/434.11 No. A 98 4- (4 '-NO2-C6H4i) -thienyl-2 900 4- (2'-N0 2
'-C
6 H4) -thienyl-2 101 4- (4'-N2-C 6
H
4 -thienyl-2 102 (3 '-CN-C 6
H
4 -thienyl-2 103 4- (2 '-CN-C 6
H
4 -thieriyl-2 104 4- (4'-C1-C 6
H
4 -thienyl-2 105 4- (3 '-C1-C 6
H
4 106 4- (2 '-C1-C 6
H-
4 -thienyl-2 107 thienyl-3 108 5-CHI-thienyl-3 109 5-CH 5 -thienyl-3 ilo 5- (4 '-CH 3
-C
6
H
4 -thienyl-3 ill 5- (3 ICH3:C6H 4 thieflyl-3 112 5- (2 '-CI-C 6
H
4 -thienyl-3 113 5- (4 '-CH 3 0-C 6
H
4 -thienyl-3 114 5- (3 '-CH 3
O-C
6
H
4 -thienyl-3 115 5- (2 '-CH 3
O-C
6
H
4 -thienyl-3 116 5- (4 '-N0 2
-C
6
H
4 -thienyl-3 117 5- (3 '-N0 2
,-C
6
H
4 -thienyl-3 118 5- (2 '-N0 2
-C
6
H
4 -thienyl-3 119 5- (4 -CN-CEH4) -thienyl-3 120 5- (3 '-CN-C 6
H-
4 -thienyl-3 121 5- (2'-CN-C 6
H
4 -thienyl-3 122 5- (4 '-C1-C 6
H
4 -thienyl-3 123 5- (3 '-C1-C 6
H-
4 -thienyl-3 124 5- -C1-C 6 H4 -thienyl-3 125 pyrazolyl-4 126 N-CWi-pyrazolyl-4 127 N-C,.H,-pyrazolyl-4 128 N- (4 '-CH j-C 6
H
4 -pyrazolyl-4 129 N- (3'-CH- 3
-C
6
H
4 -pyrazolyl-4 130 N- (2'-CHI-C 6
H
4 -pyrazolyl-4 131 N-4 '-CH iO-CtH 4 -pyrazolyl-4 132 N- (3 -CR 4 -pyrazoly1-4 133 N- (2 '-CH 40-C,H4 -pyrazolyl-4 C
C
C. C
CC
GC CC C C a an.
C
CC a a.
CCCC
CCC.
C
CC..
1 BASF' Aktiengeellscha~ft 900 05/31 920400 O.Z. 0050/43411 No. A 134 N- (4'-NO2-C6H-4) -pyrazolyl.-4 135 N- (3'-N0 2
-C
6
H
4 -pyrazolyl-4 136 N- (2 '-N0 2
,-C
6
H
4 -pyrazolyl-4 137 N- (4 '-CN-C 6 H4 -pyrazolyl-4 138 N- (3 '-CN;-C 6
H
4 -pyrazolyl-4 139 N- (2 '-CN-C 6
H
4 -pyrazolyl-4 140 N- (4 '-C1-C 6
H
4 -pyrazolyl-4 141 N- (3 '-C1-C 6
H
4 -pyrazolyl-4 142 N- (2 '-C1-C 6 1- 4 -pyrazolyl-4 143 3-CH 3 -N-methylpyrazolyl-4 144 3-C 6
H
5 -N-methylpyrazolyl-4 145 3- (4 '-CH.1-C 6
H
4 -N-rethylpyrazolyl-4 146 3- (3 '-CH-A-C 6
H
4 -N-methylpyrazolyl-4 147 3- (2 '-CH-I-C 6
H
4 -N-methylpyrazolyl-4 148 3- (4 '-CH 3
O-C
6
H
4 -N-rethylpyrazolyl-4 149 3- (3 '-CH.
3
O-C
6
H
4 -N-methylpyrazolyl-4 150 3- (2 '-CH 3
O-C
6
H
4 -N-methylpyrazolyl-4 151 3- (4 6
H
4 -N-methylpyrazolyl-4 152 3- (3 '-N0 2
-C
6
H
4 -N-methylpyrazolyl-4 153 3- (2 6
H-
4 -N-methylpyrazolyl-4 154 3 (4 '-CN-C 6
H
4 -N-rnethylpyrazolyl-4 155 3- (3'-CN-C 6
H
4 -N-methylpyrazolyl--4 156 3- (2 '-CN-C 6
H-
4 -N-methylpyrazolyl-4 157 3- (4 '-Cl-C 6
H
4 -N-methylpyrazolyl-4 158 3- (3 '-C1-C 6
H
4 -N-methylpyrazolyl-4 159 3- (2 '-C1-C 6
H
4 -N-rnethylpyra zolyl-4 160 161 3-CHi-isoxazoly1-5 162 3-C,,H,-isoxazo1y1-5 163 3- (4 '-CI--C 6
H
4 164 3- (3 '-CH 3
-C
6
H-
4 165 3- (2 '-CI-C 6
H
4 166 3- (4 '-CHIO-C 6 1 4 167 3- (3'-CH jO-ChH 4 168 3- (2 '-CHWO-C 6
H
4 169 3-(4'-NO -C 6
H
4 0 0**000 0O 0* 0*Se** 0 9* 0 0 0* 0 0000 0* 06 00 0
S
0*0 0 S~ 90 0 BASF Aktiengesa11schaft 920400 90400o.z. 0050/43411 0* 0000 00 0000 ~0 0 No.- A 170 3- (3 '-NOL-C6H4) 171 3- (2'--N0 2
-C
6
H-
4 172 3- (4 -CN-C 6 H-4) 173 3- (3 '-CN-C 6
H
4 174 3- (2 '-CN-C 6
H
4 175 3- (4 -C1-C 6 4 176 3- (3 '-C1-C 6
H
4 177 3- (2 '-C1-C 6
H-
4 178 179 3--CWi-4-chloroisoxazolyl-5 180 3-Cf.H 5 -4-chloroisoxazoly1-5 181 3- (4 '-CH 3
-C
6
H
4 182 3- -CH 3
-C
6
H
4 183 3- -CH 3
-C
6
H
4 184 3- (4 '-CH 3
O-C
6
H
4 185 3- (3 '-CH 3
O-C
6
H
4 186 3- (2 '-CHIO-CAH) -4-chloroisoxazoly1-5 187 3- (4 '-N0 2
-C
6
H
4 188 3- (3 '-N0 2
-C
6
H
4 189 3- (2 '-N0 2
-C
6
H
4 190 3- (4 '-CN-C 6
H
4 -4-chloroisoxazoly1-5 191 3- (3 '-CN-C 6
H
4 192 3- (2 '-CN-C 6
H
4 193 3- (4 '-C1-C 6
H-
4 194 3- (3 '-C1-C 6
H
4 195 3- Cl C 6
H
4 196 isoxazolyl-3 197 5-CHt-isoxazoly1-3' 198 5-CiH,,-isoxazolyl-3 199 5- (4 '-CH,-C6H 4 -isoxazoly1-3 200 5- (3 '-CHI-C 6
H
4 -isoxazolyl-3 201 5- (2 '-CH 3
-C
6 H) -isoxazoly1-3 202 5- (4 '-CH-iO-C 6
H-
4 -isoxazoly1-3 203 5- (3 '-CIHO1-CH 4 -isoxazolyl-3 204 5- (2'-CH-iO-C 6
H
4 -isoxazoly1-3 205 5- (4 -NO' -C1- 4 -isoxazolyl-3 00 0 0* 00 BA~SF Aktiengeaellachaft 920400 0. Z. 0050/43411,
C.
C. CC
C
*CCC
C
No. A 206 5- (3 '-N0 2
-C
6
H
4 -isoxazolyl-3 207 5- (2 '-N0 2
-C
6
H
4 -isoxazolyl-3 208 5- (4 1 -CN-C 6 H4) -isoxazolyl-3 209 5- (3 '-CN-C 6
H
4 -isoxazolyl-3 210 5- (2 '-CN-C 6
H
4 -isoxazolvl-3 211 5- (4'-Cl-C 6
H
4 -isoxazolyl-3 212 5- (3 '-C1-C 6
H
4 -isoxazolyl-3 213 5- (2 '-C1-C 6
H
4 )-isoxazolyl-3 214 215 3-CH 3 216 3-C 6
H
5 217 3- (4 '-CH.1-C 6
H
4 218 3- (3 '-CH 3
-C
6
H
4 219 3- (2 '-CH 3 -C6H 4 1220 3- (4 '-CH 3
O-C
6
H
4 221 3- (3 '-CH' 4
-C
6
H
4 222 3- (2 '-CH 3
O-C
6
H
4 223 3- (4 '-N0 2
-C
6
H
4 224 3- N0 2
!-C
6
H-
4 225 3- -N0 2
-C
6
H
4 226 3-(4'-CN-C 6
H
4 227 3- (3 '-CN-C 6
H
4 -i 228 3- (2 '-CN-C 6 H4) 22343 2-C-xazo)y-4stizo 235 2- (4 '-CHl-C 6
H
4 -oazolyl- 236 2- (3 '-Cl--C 6
H-
4 -ioazolyl- 237 2-2CH3-xaC 6 Hl 4 oaly4 238 2- (4 1 -CH.-C 6
H-
4 -oxazoy-4 239 2- (3 '-CI-OC6H 4 -oxazolyl-4 240 2- (2 '-CHO-CbH4) -oxazoly1-4 241 (4 -NO. -C6H 4 -oxazolyl-4 4 BASF XkJtiengeaellacbhaft 920400 O.2Z. 0050/4~3411 S S
S.
S. S *5*S S. *S
*SSS
S. No. A 242 2- (3 '-N0 2
-C
6
H
4 -oxazolyl-4 243 2- (2 '-NO---C6H 4 -oxazolyl-4 244 2- (4 '-CN-C6H-4 -oxazolyl-4 245 2- (3 '-CN-C 6
H
4 -oxazoly1-4 246 2- (2 '-CN-C 6
H
4 -oxazolyl-4 247 2- (4 '-Cl-C 6 1- 4 -oxazolyl-4 248 2-1(3 '-C1-C 6
H
4 -oxazolyl-4 249 2- (2 '-C1-C 6
H
4 -oxazolyl-4 250 thiazolyl-4 251 2-CH 3 -thiazolyl-4 252 2-C 6
H
5 -thiazolyl-4 253 2- (4 '-CH 3
-C
6
H
4 -thiazolyl-4 254 2- (3 '-CH 3
-C
6
H
4 -thiazolyl-4 255 2- -CH 3
-C
6
H
4 -thiazolyl-4 256 2- (4 '-CH 3
O-C
6
H
4 -thiazolyl-4 267 2- (3 '-CH 3
O-C
6
H
4 -thiazolyl-4 258 2- (2 '-CH- 3 0-C 6
H
4 -thiazolyl-4 259 2- (4 6
H
4 -thiazolyl-4 260 2- (3 '-N02-C6H 4 -thiazolyl-4 261. 2- (2'-NO -C 6 1- 4 -thiazolyl-4 262 2- (4'-CN-C 6
H
4 -thiazolyl- 4 263 2- (3 '-CN-C6H 4 -thiazolyl-4 264 2- (2'-CN-C 6
H
4 -thiazolyl-4 265 2- (4 '-Cl-C6H- 4 -thiazolyl-4 266 2- (3 '-CiL-C 6
H
4 -thiazolyl-4 27 2- (2 '-Cl-C6H4 -thiazolyl-4 268 N-CH 3 -1,2,4-tr4iazolyl-5 269 3-CI--N-CH 3 -1,2,4-triazolyl-5 270 3-C6H 5
-N-CH
3 -1 272. 3-(4 '-CH 3
-C
6
H
4
-N-CH
3 -1,2,4-triazoll-5 272 3- (3 '-CHI-C 6
H
4
-N-CH
3 -1 273 3- (2 '-CH-CEH- 4 2, 274 3- (4 '-CH O-C 6
H-
4 -N-CI-1, 2, 275 13-(3 '-CI{-C 6
H
4
-N-CH
3 2, 276 13- (2'-CH 4
O-C
6
H
4
-N-CH
3 2, 277 j3- (4 -NO-C6H 4 -N-CH-4-1, 2, 4-,.riazoly1-5 BkSP Aktiengeaellnchaft 900 05/31 920400 O.Z. 0050/43411
C
C
*.CC
No. A 278 3- (3 6
H
4 -N-CH3-1 279 3- (2 '-N02-C6H4) -N-CH 3 2,4-triazolyl-5 280 3- (4'-CN-C6H-4) -N-CH3-1,2, 281 3- (3'-CN-C 6
H
4 -N-CHI-1, 2, 282 3- (2 '-CN-C 6
H
4
-N-CH
3 -1 283 3- (4'-Cl-C 6 H4) -N-CH 3 284 3- (3 '-Cl-C 6
H
4 -N-CHI-1,2, 285 3- -Cl-C 6
H
4
)-N-CH
3 -1 286 1,3,4-oxadiazolyl-2 287 5-CH 3 3, 4-oxadiazolyl-2 288 5-C 6
H
5 3 4 -oxadiazolyl-2 289 5- (4'-CH 3
-C
6
H
4 3, 4-oxadiazolyl-2 290 5- (3'-CH3-C 6
H
4 3, 4-oxa.cdiazoly1-2 291 5- (2'-CH3-C 6
H
4 -1,3,4-oxadiazolyl-2 292 5- (4 '-CH3O-C 6
H
4 -1,3,4-oxadiazolyl-.2 293 5- (3'-CH 3
O-C
6
H
4 3, 4-oxadiazolyl-2 294 5- (2 '-CH 3
O-C
6
H
4 3, 4-oxadiazolyl-2 295 5- (4 '-N0 2
,-C
6
H
4 4-oxadiazolyl-2 296 5- (3 '-N02-C6H- 4 -1,3,4-oxadiazolyl-2 297 5- (2 '-N02-CCH- 4 3, 4-oxadiazolyl -2 298 5- (4'-CN-C 6
H
4 3, 4-oxadiazolyl-2 299 5- (3'-CN-C6H 4 3,4-oxadiazolyl-2 300 5- (2'-CN-C6H4) 4-oxadiazolyl-2 301 5- (4'-Cl-CrH4) l,3, 4-oxadiazolyl-2 302 5-(3'-C1-C6H4) 1,3, 4-oxadiazolyl-2 303 5- (2 '-C-C 6
H
4 3, 4-oxadiazolyl-2 304 1,2 ,-oxadiazolyl 3 305 5-C-1, 2, 4-oxadiazolyl-3 306 5-Ch-l, 2, 4-oxadiazolyl-3 307 5- (4'-CH3-C 6 H4 4 4-oxadiazolyl-3 308 5- (3 '-CH 3
-C
6
H
4 4-oxadiazolyl-3 309 5- (2'-CH.1-C 6
H
4 -1,2,4-oxadiazolyl-3 310 5- 4 1 -C~i-O-C6H- 4 4-oxadiazolyl-3 311 5- (3 '-CH3O-C 6
H
4 2, 4-oxadiazolyl-3 312 5- (2 '-Cl-I-0-CH 4 4-oxadiazolyl-3 313 15-(4'I-NO2-C 6
H
4 4-oxadiazolyl-3 B EASF Aktiengesellaclaft 920400e o.z. 0050/43411 No. A 314 5- (3'-N 2
C
6
H-
4 -1,2,4-oxadiazolyl-3 315 5- (2'-N0 2
-C
6
H-
4 -1,2,4-oxadiazolyl-3 316 5- (4'-CN-C 6
H
4 2, 4-oxadiazolyl-3 317 5- (3'-CN-C 6
H
4 4-oxadiazolyl-3 318 5- (2'-CN-C 6
H
4 4--oxadiazolyl-3 319 (4'-Cl-C 6
H
4 -1,2,4-oxadia..-,.Lyl-3 320 5- (3'-Cl-C 6
H
4 -1,2,4-oxadiazolyl-3 321 5- 1Cl C 6
H
4 -1,2,4-oxadiazolyl-3 322 1,2,4-oxadiazolyl-5 323 3-CH 3 -1,2,4-oxadiazolyl-5 324 3-C6H5-1 325 3- (4'-CHI-C 6
H-
4 -1,2,4-oxadiazolyl-5 326 3- (3'-CH3-C 6
H
4 -1,2,4-oxadiazolyl-5 327 13- (2 '-CHI-C 6 4 328 3- (4 '-CHIO-C 6
H
4 329 3- (3'-CH~iO-C 6
H
4 330 (2 '-CH0-C 6
H
4 332 3- (3'-NO 2
-C
6
H
4 -1,2,4-oxadiazolyl-5 333 3- (2'-N0 2
-C
6
H
4 -1,2,4-oxadiazolyl-5 334 3- (4'-CN-C 6
H
4 -1,2,4-oxadiazolyl-5 335 3- (3'-CN-C 6
H
4 -1,2,4-oxadiazolyl-5 336 3- (2'-CN-C 6
H
4 -1,2,4-oxadiazolyl-5 337 3- (4'-Cl-C 6
H
4 -1,2,4-oxadiazolyl-5 338 3- (3'-Cl-C 6
H-
4 -1,2,4-oxadiazolyl-5 339 3- (2 '-Cl-C 6
H
4 340 1,2, 4-thiadiazolyl-3 341 5-CH3-1 ,2 ,4-thiadiazolyl-3 342 5-Ci.Hr,-1, 2,4-thiadiazolyl-3 343 5- (4'-CH-i-C 6
H
4 -1,2,4-thiadiazolyl-3 344 -C 6
H
4 -1,2,4-thiadiazolyl-3 345 5- (2'-CHi-C 6
H
4 -1,2,4-thiadiazoly1-3 346 5-WC-0CH)-,,4tidaoy- 347 5- (3'-CH O-CE 4 4-thiadiazolyl-3 348 5- (2'-CH 3
O-C
6
H
4 -1,2,4-thiadiazolyl-3 349 15-(4'-NO: -C6H-1,, 4-thiadiazolyl-3 BASF Aktiengesellschaft 900 OZ.05/31 920400 O.Z. 0050/43411 0 *5
S
000.
No. A 350 5- (3 '-NO 2
-C
6
H
4 2, 4-thiadiazoiyl-3 351 5- (2 '-N0 2
-C
6
H
4 4-thiadiazolyl-3 352 5- (4'-CN-C 6
H
4 4-thiadiazolyl-3 353 5- (3 '-CN-C 6
H
4 2, 4-thiadiazolyl-3 354 5- (2 "-CN-C 6
H
4 4-thiadiazolyl-3 355 5- (4 -C1-C 6
H
4 2, 4-thiadiazolyl-3 356 5- (3 '-C1-C 6
H
4 2, 4-thiadiazolyl-3 357 5- (2 '-Cl-C 6
H
4 2, 4-thiadiazolyl-3 358 1,3, 4-thiadiazolyl-2 359 5-CHI-1, 3, 4-thiadiazolyl-2 360 5-C 6
H
5 -1 4-thiadiazolyl-2 361 5- (4 '-CH3-C 6
H
4 3, 4-thiadiazolyl-2 362 5-(3 '-CH 3
-C
6
H
4 3 4--thiadiazolyl-2 363 5- (2 '-C-1 3
-C
6
H
4 3 4-thiadiazolyl-2 364 5- (4'-CH 3 0-C 6
H
4 -1,3,4-thiadiazolyl-2 365 5- (3'-CH 3 0-C 6
H-
4 3,4-thiadiazolyl-2 366 5- (2'-CH 3
O-C
6
H
4 -1,3,4-thiadiazolyl-2 367 5- (4'-N0 2
,-C
6
H
4 -1,3,4-thiadiazolyl-2 368 5- (3'-NO 2
-C
6
H
4 -1 3,4-thiadiazolyl-2 369 5- (2 '-N0 2
-C
6
H
4 -1,3,4-thiadiazolyl-2 370 5- (4 '-CN-C 6
H
4 3, 4-thiadiazolyl-2 371 5- (3 '-CN-C 6
H
4 3, 4-thiadiazolyl-2 372 5- (2 '-CN-C 6
H
4 3, 4-thiadiazolyl-2 373 5- (4'-Cl-C 6
H
4 3, 4-thiadiazolyl-2 374 5- (3 '-C1-C 6
H-
4 3,4-thiadiazolyl-2 375 5- (2 '-Cl-C 6
H
4 3,4-thiadiazolyl-2 376 pyridinyl-2 377 pyridinyl-4 378 pyridazinyl-3 379 pyridazinyl-4 380 pyridazinyl-2 381 pyrirnidinyl-4 382 383 pyrimidinyl-2 L 384 pyridinyl-3 1 9ASF K.ktiengesellachaft 920400 O.Z. 0050/43411 Table 3 .c Ar.
IR( cm 1 or No. Compound IR(c- rmp NH-NMR( ppm 1 3.8 3 H); 3.65 3
H)
H3CO 2
~CH
3 v "6.6 I 3.9 3 H); 3.65 (s3 H) 2
OCH
3
CI
3 S 104 H3CO2C 113 ci 6.6 I 3.9 3 H); 3.7 3 H) 4 0 0 H3CO 2
C
0%
H
3 CH3 0 CH H3CO 2 CH3 BASF AktJiengesellachafte 920400 O.Z. 0050/43411
A
No. Compound IR cm- )or m IH-NMR( ppm m 0 01 3 76 H3CO 2 C CH 3 l1 3
C
2 853
CH
3 7.5 I 3.8 H);
CH
3 3.7 3 H)
H
3
CO
2 C CH3 6.55 I 3.9 3 H); O~o
CH
3 3.7 3 H) 9 H3CO 2 C 0
CH
I 3.8 H); 1o z, 0*N3. 3 H) Z!%0 H3CO2C
-~CU
3 I BASF 2Aktiongese11achaft 920400 O.Z. 0050/43411 4.
C. C *g.
C.
*444 96** No. Compound IR cm- 1 )or m 1 H-NMR( ppm )fi 11 01N H H3C2C ON.CH 6 H3N2 CH 3 67 0 0, N 13 H3C 2 C 0 H3 823 0 0 14 H 3
CO
2 CZ CH3 125
CH
3 __127 slo NNN H3CO2 CH3CI #4 4 C BASF Aktiengeoellachaft No. Compound 16
H
3 CO2C Ci 17 [Z 0~~~C
:H
3
C
2 C- Cl 19 H3C O22C 19 0 920400 o.z. 0050/43411 I f IBASF'Aktiengesellochaft 920400 O.Z. 0050/43411 No. CompoundIR cm- )or m No. Copound H-NMR( ppm) 21 0I 91
H
3
C
2 C NCH 3 1 3.75 H); 3.65 3 H) 22
N
H3CO 2 C CH3 23 098 7,55 11H); 3.8 3 H); 3.65 3 H) 2 4 0 3 O 2 O .4'
H
3 CO z(C N CH 3 N '12 BASF Aktiengesellachaft 900 05/31 920400 O.Z. 0050/43411 IR cm- )or No. Compound IH-NNIR( ppm )p es,. N- CH22 isomers (approx. 3 26 0 ~7.5 (2 s, 1 3.8 (2 s,3 H); 26i 0 CH3j 3.65 (2 s, 3H) H3CO2C
CH
3 CH3
H
3 C I 27 74 cl 2811
H
3
CO
2 C 0CH 3
N-
7.55 1 3.8 3 H); 3.7 3 H) 29 C
H
3
CO
2 C CH3 1 3.75 3 H); 3.65 3 H) H 0 300 -S BASF'Aktiengesellochaft 920400 O.Z. 0050/43411 c n No. Compound IR( cm 1 )ormp 1 -NMR ppm 7.45 1 3.8 3 H); 3.65 3 H)
H
3
CO
2 C
CH
3 I 3.85 3H); 3.65 3
H)
3 x \H 3
C
2
C
0- CH 3 33 0I0,Y 123
H
3
CO
2
CH%%N
"Cl 7.45 I Hi); 3.75 3 H); 3.6 3 H) l1 3
CO
2 C H Ci 7.55 3.85 (s,3 H); 3.7 3H) 0I%1 96 0
O-N
H
3
CO
2 C
.CH
I3ASPF ltienqese11rochaft 9200 oz00/4:& 920400 O.Z. 0050/43411 No. CompoundIR cm-1 )or m No. Comound ll-NMR( ppm) 36 0 0129 38S 3.6 Ns 3 H) H3CO 2 C CH3 (S );38(s CH3 CH CH3H) 11H); 3. 3 H); 3.65(s, 3H) l13O III /C
H
3
CO
2 C BAsF 'Aktienoesellachaft 920400 O.Z. 0050/43411 V..so.
0 a.
BASF Aktiengesellschiaft 920400 O.Z. 0050/43411 BASF 'Aktiengese11schaft 900 0~/31 920400 O.Z. OC")0/43411 a BASFAktiengesellschaft 920400 O.Z. 0050/43411 9* 9 9.
ft 9 99*9 9 BASF-Aktiengesellschaft 920400 O.z. 0050/43411 t
C
I S S PS. S
P
S.
*P*S
S
S I' I ASF Aktiengesellschaft 900 05/31 920400 O.Z. 0050/43411 BASF 'Aktiengesellachaft 920400 O.Z. 0050/43411 ~~v1 BASF 'Aktiengesellschaft 920400 o.Z. OO5O/4 411 0 BASF'Aktiengesellschaft 920400 O.Z. 0050/43411.
78 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 suspensions), dispersions, emulsions, oil dispersions, pastes, dusts, broadcasting agents, or granules by spraying, atomizing, dusting, broadcasting or watering. The forms of application 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 dispersants; if water is used as solvent, it is also possible to employ other organic solvents as auxiliary solvents. Suitable auxiliaries for this purpose are solvents such as aromdtics xylene), chlorinated aromatics chlorobenzenes), paraffins crude oil fractions), alcohols methanol, butanol), ketones cyclohexanone), amines ethanolamine, dimethylformamide), and water; carriers such as ground natural minerals kaolins, aluminas, talc and chalk) and ground synthetic minerals highly disperse silica and silicates); emulsifiers such as nonionic and anionic emulsifiers 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, naphthalenesulfonic acid and dibutylnaphthalenesulfonic acid, and of fatty acids, clkyl and alkylaryl sulfonates, and alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated r 'BASF'Aktiengesellschaft 920400 o.z. 0050/43411 79 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 isooctylphenol, 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 polyoxypropylene, 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, 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 o 25 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.
a.
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 L I BASF Aktiengesellschaft 920400 O.Z. 0050/43411 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 compound no. 3 from Table 3, 40 parts by weight of cyclohexanone, 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 parts by weight of compound no. 4 from Table 3, 25 parts by weight of cyclohexanol, parts by weight of a mineral oil fraction having a boiling point between 210 and 2800C, 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 compound no. 5 from Table 3, 3 parts by weight of the sodium salt of diisobutylnaphthalene-a-sulfonic acid, 10 parts by weight of the sodium salt of a lignin-sulfonic acid obtained S"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.
25 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 48 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 dodecylbenzenesulfonic acid, 8 parts by BASF'Aktiengesellschaft 920400 O.Z. 0050/43411 81 weight of a fatty alcohol polyglycol ether, 2 parts by weight of the sodium salt of a phenolsulfonic acid-ureaformaldehyde condensate and 68 parts by weight of a paraffinic 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 ingredients.
Application may be effected before or after infection of the 25 materials, plants or seed by the fungi.
The compounds I are particularly useful for controlling the Sfollowing plant diseases: Erysiphe graminis in cereals, Erysiphe cichoracearum and Sphaerotheca fuliginea in cucurbits, Podosphaera leucotricha in apples, Uncinula necator in vines, J: 35 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 barley, SBASF Aktiengesellchaft 920400 O.Z. 0050/43411 82 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 materials (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, rates 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 invention may also be present together with other active ingredients, for example herbicides, insecticides, growth regulators, other fungicides, or fertilizers.
o.
25 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 methyl 2 -(2-hydroxyphenyl)-3-methoxyacrylate disclosed in EP 251 082.
35 nUse Example 1 Action on Plasmopara viticola Leaves of potted vines of the Mller-Thurgau variety were sprayed with aqueous suspensions containing (dry basis) 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'Aktiengesellsrhaft 920400 O.Z. 0050/43411 83 Plasmopara viticola. The plants were first placed for 48 hours in a water vapor-saturated chamber at 24 0 C 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, 10, 11, 12, 13, 15, 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 than prior art comparative agent A 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 22 0 C in a high-humidity (90 95%) chamber. During this period the Sspores 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- 25 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 better fungicidal action than prior art comparative com- S 35 pound A

Claims (10)

1. A substituted acrylate of the formula I x Y B N OR 2 R'0 2 C where B is alkyl which is substituted by 1-4 identical or different substituents R 3 alkenyl which is substituted by 1-4 identical or different substituents R4, alkynyl which is substituted by 1-4 identical or different substituents cycloalkyl which is substituted by 1-4 identical or different substituents R 6 cycloalkenyl which is substituted by 1-4 identical or different substituents R cycloalkynyl which is substituted by 1-4 identical or different substituents R 8 or heterocyclyl which is substituted by 1-4 identical or different substituents R 9 15 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, cycioalkynyloximino, 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- 85 O.Z. 0050/43411 carbonyl, arylaniinocarbonyl, hetarylaminocarbonyl, heterocyclylaminocarbonyl, alkyithic, alkenylthio, alkynyithio, cycloalkylthio, arylthio, hetarylthio, heterocyclylthio, cycloalkenylthio, cycloalkynylthio, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, arylamino, hetarylamino, heterocyc lyl amino, cycloalkenyl- amino, cycloalkynylamino, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, het- arylcarbonyl, heterocyclylcarbonyl, cycloalkenylcarbonyl, cycloalkyny, carbonyl, alkylsulfoxyl, alkenylsulfoxyl, alkynylsulfioxy1, cycloalkylsulfoxyl, arylsulfoxyl, hetarylsulfoxyl, heterocyclylsulfoxyl, cycloe'.ikynyl- sulfoxyl, cycloalkenylsulfoxyl, alkylsulfonyl, alkenyl- sulfonyl, alkyiylsulfonyl, cycloalkySlsulfonyl, aryl- sulfonyl, hetarylsulfonyl, heterocyclylsulfonyl, cyc lo- alkenylsulfonyl, cycloalkynylsulfonyl, alkylsulfinyl, alkenylsulfinyl, alkynylsulfinyl, cycloalkylsulfinyl, *too*:arylsulfinyl, hetarylsulfinyl, heterocyclylsulfinyl, *.:cycloalkenylsulfinyl, cycloalkynylsulfinyl, alkyl- carbonyloxy, alkenylcarbonyloxy, alkynylcarbonyloxy, cycloalkylcarbonyloxy, tycloalkenylcarbonyloxy, cyclo- alkynyic arbonyloxy,, aryic arbonyloxy, hetaryic arbonyloxy, heterocyclylcarbonyloxy, alkylcarbonylamino, aJ2.teny1- .carbonylamino, alkynylcarbonylamino, cycloalkylcarbonyl- amino,' cycloalkenylcarbonylemino, cycloalkynylcarbonyl- a ino arylc arbonyl amino, hetarylc arbonyl amino, hetero- cyclylcarbonylamino, cycloalkylalkoxy, cycloalkenyl- alkoxy, cylcoalkynylalkoxy, arylalkoxy, hetarylalkoxy or heterocyc lylalkoxy, if X and Y are on adjacent carbon atoms, they may be condensed to form an v-uisubstituted or substituted aroma- tic or heteroaromatic, alicyclic or heterocyclic, par- tially or completely hydrogenated ring, R 1 and R 2 may be substituted and independently of one another are each alkyl, alkenyl, alkynyl, cycloalkyl or cyclvoalkenyl, R 3 and R 4 may be substituted by 1-4 identi- cal or different substituents R 10 and R 3 and R 4 are each 86 O.Z. 0050/43411 n itro, haloalkoxy, alkoxy, alkynyl, cycloalkyl, hetaryl, heterocyclyl, cycloalkenyl, cycoalkynyl, alkenyloxy, alkynyloxy, cycloalkoxy, hetaryloxy, heterocyclyloxy, cycloalkenyloxy, cycloalkynyloxy, alkoximino, alkenyl- oximino, alkynyloximino, cycloalkyloximino, cycloalkenyl- oximino, cycloalkynyloximino, aryloximino, hetaryIlox- imino, heterocyclyloximino, cycloalkyloxycarbonyl aryloxycarbonyl, hetaryloxycarbonyl, heterocyclyloxy- carbo-nyl, cycloalkenyloxycarbonyl, cycloalkynyloxy- carbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkenylaminocarbonyl, dialkenylam.4nocarbonyl, alkynyl- aminocarbonyl, dialkynylaminocarbonyl, cycloalkylamino- carbonyl, cycloalkenylaminocarbonyl, cycloalkynylamino- carbonyl, arylaminocarbonyl, hetarylaminocarbonyl, heterocyclylaminocarbonyl, alkyithic, alkenyithio, alkynyithic, cycloalkylthio, arylthio, hetarylthio, heterocyclylthio, cycloalkenylthio, cycloalkynylthio, alkylaiuino, alkenylamino, alkynylamino, cycloalkylamino, arylamino, hetarylamino, heterocyc lyl amino, cycloalkenyl- amino, cycloalkynylamino, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, het- arylcarbonyl, heterocyclylcarbonyl, cycloalkenylcarbonyl, *cycloalkynylcarbonyl, alkylsulfoxyl, alkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl, arylsulfoxy1, 25 hetarylsulfoxyl, heterocycly1sulfoxyl, cycloalkynyl- sulfoxyl, cycloalkenylsulfoxyl, alkylsulfonyl, alkenyl- sulfonyl, alkynylsulfonyl, cycloalkylsulfonyl, aryl- sulfonyl, hetarylsulfonyl, heterocyclylsulfonyl, cyclo- alkenylsulfonyl, cycloaJlkynylsulfonyl, alkylsulfinyl, alkenylsulfinyl, alkynylsulfinyl, cycloalkylsulfinyl, aryisulfinyl, hetarylsulfinyl, heterocyclylsulfinyl, cycloalkenylsulfinyl, cycloalkynylsulfinyl, alkyl- *:carbonyloxy, alkenylcarbonyloxy, alkynylcarbonyloxy, cycloalkylcarbonyloxy, cycloalkenylcarbonyloxy, cyclo- alkynylcarbonyloxy, arylcarbonyloxy, hetarylcarbonyloxy, heterocyclylcarbonyloxy, alkylcarbonylamino, alkenyl- carbonylatino, alkynylcarbonylamino, cycloalkylcarbonyl- 87 O.Z. 0050/43411 amino, cycloalkenylcarbonylamino, cycloalkynylcarbonyl- amino, arylcarbonylamino, hetarylcarbonylami- 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, aikenylox- iminoalkenyl, alkynyloximinoalkenyl, cycloalkoximino- alkenyl, cycloalkenyloximinoalkenyl, cycloalkynyloximino- alkenyl, aryloximinoalkenyl, hetaryloximinoalkenyl or heterocyclyloximinoalkenyl, R 5, R6, R 7 and R 8 may be substituted by 1-4 identical or different substituents R 10 and R 5 Rr, R 7 and Ra are each nitro, haloalkyl, alkyl, haloalkoxy, alkenyl, alkynyl, cycloalkyl, aryl, hetaryl, heterocyclyl, cycloalkenyl, cycloalkynyl, alkoxy, alkenyloxy, alkynyloxy, cyclo- alkoxy, aryloxy, hetaryloxy, heterocyclyloxy, cyclo- *leylxl .ylakyyoy *loiio leyoii alkenyloxyli, cycloalkylykoximino, alkenyloximino, cyc loalkynyloximino, 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, alkenyithic, alkynylthio, cycloalkylthio, arylthio, hetarylthio, heterocyclyithic, 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, c.,ycloalkylsulfoxy1, 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, heterocyc lylcarbon- yloxy, alkylcarbonylaiino, alkenylc arbonyl amino, alkynyl- carbonylamino, cycloalkylcarbonylamino, cycloalkenyl- carbonylamino, cycloalkynylcarbonylamino, arylcarbonyl- amino, hetarylcarbonylamino or heterocyclylcarbonylaiino, R9 may be substituted by 1-4 identical or different substituents R 10 and R 9 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, 6Y)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, cycloalkyithio, 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, hetaryl carbonyloxy, heterocyclylcarbon- yloxy, alkylcarbonylamino, alkenylc arbonyl amino, alkynyl- carbonylamino, cycloalkylcarbonylamino, cycloalkenyl- carbonjlamino, cycloalkynylcarbonylamino, arylcarbonyl- amino, hetarylcarbonylamino, heterocyclylcarbonylamino, cycloalkylaikoxy, cycloalkenylalkoxy, cycloalkynylalkoxy, arylalkoxy, hetarylalkoxy or heterocyclylalkoxy, R10 may be substituted by 1-4 identical or different substituents R" and R 10 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 cycloalkynylo 'ximino, aryloximino, hetaryloximino, hetero- cyclyloximino, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, cycloalkoxycarbonyl, aryloxycarbonyl, hetaryloxycarbonyl, heterocyclyloxycarbonyl, cyc lo- alkenyloxycarbonyl, cycloalkynyloxycarbonyl, alkyl- aminocarbonyl, dialkylaminocarbonyl, alkenylamino- carbonyl, dialkenylaminocarbonyl, alkynylazuinocarbonyl, dialkynylaminocarbonyl, cycloalkylaminocarbonyl, cyclo- alkenylaminocarbonyl, cycloalkynylaminocarbonyl, arylaminocarbonyl, hetarylaminocarbonyl, heterocyclylaminocarbonyl, alkylthio, alkenylthio, alkynyithia, cycloalkyithio, arylthio, hetarylthio, heterocyclylthio, cycloalkenylthio, cycloalkynylthio, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, arylamino, hetarylamino, heterocyciviamino, cycloalkenylamino, cycloalky'iylamino, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, hetarylcarbonyl, heterocyclylcarbonyl, cycloalkenylcarbonyl, cycloalkynylcarbonyl, alkylsuif ox- yl, alkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl, arylsulfoxyl, hetarylsulfoxyl, heterocyclylsulfoxyl, cycloalkynylsulfoxyl, cycloalkenylsulfoxyl, alkyl- :sulfonyl, alkenylsulfonyl, alkynylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, hetarylsulfonyl, hetecocyclylBUlfonyl, cycloalkenylsulfonyl, cylcoalkynylsulfonyl, alkylsulfinyl, alkenylsulfinyl, alkynylsulfinyl, cycloalkylsulfinyl, arylsulfinyl, hetarylsulfinyl, heterocyclylsulfinyl, cycloalkenyl- Sul f iyyl, cycloalkynylsulfinyl, alkylcarbonyloxy, alkenylcarbonyloxy, alkynyi~carbonyloxy, cycloalkylcarbon- yloxy, cycloalkenylcarbonyloxy, cycloalkynylcarbonyloxy, .Ape arylcarbonyloxy, hetarylcarbonyloxy, heterocyclylcarbon- yloxy, alkylcarbonylamino 1 alkenylcarbonylamino, alkynylN carbonylamino, cycloalkcitrbonylamino, cycloalkenyl- carbonylamino, cycloalkyty:Lcarbonylamino, arylcarbonyl- amino, hetarylcarbonylaminco, heterocyclylcarbonylamino, cycloalkylalkoxy, cycloalkenylalkoxy, cycloalkynylalkoxy, 91 0. Z. 0050/43411 arylalkoxy, hetarylalkoxy or heterocyclylalkoxy, R 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, cycloalkyiyloxy, 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, cycloallcylaminocarbonyl, cycloalkenylaminocarbonyl, cycloalkynylaminocarbonyl, arylaminocarbonyl, hetarylaminocarbonyl, heterocyclylaminocarbonyl, alkyl- :20 thio, alkenylthio, alkynylthio, cycloalkylthio, arylthio, hetarylthio, heterocyclylthio, cycloalkenylthio, cyclo- alkynylthio, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, arylamino, hetarylamino, heterocyclyl- amino, cyc loalkenyl amino, cyc loalkynyl amino, alkylcarbon- yl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, hetarylcarbonyl, heterocyclylcarbonyi, cycloalkenylcarbonyl, cycloalkynylcarbonyl, alkylsuif ox- yl, alkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl, V arylsulfoxyl, hetarylsulfoxyl, heterocyclylsulfoxyl, 30 cycloalkynylsulfoxyl, cycloalkenylsulfoxyl, alkylsulfonyl, alkenylaulfonyl, alkynylsulfonyl, 1.4C cycloalkylsulfonyl, arylsulfonyl, hetarylsulfonyl, :heterocyclylsulfonyl, cycloalkenyl'sulfonyl, cycloalkynylsulfonyl, alkylsulfinyl, alkenylsulfinyl, alkynylsulfinyl, cycloalkylsulfinyl, arylsulfinyl, hetarylsulfinyl, heterocyclylsUlfinyl, cycloalkenyl- sulfinyl, cycloalkynylsulfinyl, alkylcarbonyloxy, 92 O.Z. 0050/43411 alkenylcarbonyloxy, alkynylcarbonyloxy, cycloalkylcarbon- yloxy, cycloalkenylcarbonyloxy, cycloalkynyicarbonyloxy, arylcarbonyloxy, hetarylcarbonyloxy, heterocyclylcarbon- yioxy, alkylcarbonylamino, alkenylcarbonylamino, alkynyl- carbonylamino, cycloalkylcarbonylamina, 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 x Y R 3 mAikyl%% 0 R02 where R 1 R 2 R 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 x R 4 mAlkenyl,% 0 OR R'0 2 2 where R 1 R 2 X and Y have the meanings stated in *000 claim 1 and m is 1, 2, 3 or 4.
4. A substituted acrylate of the formula IV 93 O.Z. 0050/43411 OR2 where R R X and Y have the meanings stated in claim 1 and m is 1, 2, 3 or 4. A substituted acrylate of the formula V R 6 mCycloalkyk OR 2 2 1 0 00000* C* *CC* C 4 OC where R 1 R 2 R 6 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 x RWmCycloalkenyl VI 2 C OR 2 10 where R1, R R 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 RWmCycloalkiiiyl VII OR 2 2 C 94 O.Z. 0050/43411 where R 2 R X and Y have the meanings stated in claim 1 and mn is 1, 2, 3 or 4.
8. A substituted acrylate of the formula VIII x RmHeterocyclyl %%0,yVIII 2 OR 2 where R 1 R 2 R 9 X and Y have the meanings stated in claim 1 and mn is 1, 2, 3 or 4.
9. A compound of the formula IX x Y Ix OR 2 2 C wherc, R 1 R 2 X and Y have the meanings stated in claim 1. :*.Of 0.0.l *4 9S 95 O.Z. 0050/43411 A fungicide containing an inert carrier and a fungicidal amount of a substituted acrylate of the formula I X Y B 0 s O SOR 2 RIO 2 C where B is alkyl which is substituted by 1-4 identical or different substituents R 3 alkenyl which is substituted by 1-4 identical or different substituents R 4 alkynyl which is substituted by 1-4 identical or different substituents R 5 cycloalkyl which is substitu ad by 1-4 identical or different substituents R 6 cycloalkenyl which is substituted by 1-4 identical or different substituents cycloalkynyl which is substituted by 1-4 identical or different substituents R 8 or heterocyclyl which is substituted by 1-4 identical or different substituents R 9 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, :20 alkynyloxy, cycloalkoxy, aryloxy, hetaryloxy, hetero- cyclyloxy, cycloalkenyloxy, cycloalkynyloxy, alkoximino, Salkenyloximino, alkynyloximino, cycloalkyloximino, 1 cycloalkenyloximino, cycloalkynyloximino, aryloximino, hetaryloximino, heterocyclyloximino, alkoxycarbonyl, *25 alkenyloxycarbonyl, alkynyloxycarbonyl, cycloalkyloxy- ,I I. -96 O.Z. 0050/43411 carbonyl aryloxycarbonyl, hetaryloxycarbonyl, hetero- cyclyloxycarbonyl, cycloalkenyloxycarbonyl, cycloalkynyl- oxycarbonyl, alkyliLinocarbony1, dialkylaminocarbonyl, alkenylaminocarbonyl, dialkenylaminocarbonyl, alkynyl- aminocarbonyl, dialkynylaminocarbonyl, cycloalkylamino- carbonyl, cycloalkenylaminocarbonyl, cycloalkynylamino- carbonyl, arylaminocarbonyl, hetarylaminocarbonyl, heterocyclylaminocarbonyl, alkyithic, alkenylthio, alkynylthio, cycloalkylthio, arylthio.. hetarylthio, heterocyclylthio, cycloalkenylthio, cycloalkynylthio, alkylaiuino, alkenylamino, alkynylamino, cycloalkylamino, arylaniino, hetarylamino,, heterocyclylamino, cycloalkenyl- amino, cycloalkynylamino,. alkylcarbonyl,, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, het- arylcarbonyl, heterocyclylcarbonyl, cycloalkenylcarbonyl, cycloalkynylcarbonyl, alkylsulfoxyl, alkenylsulfoxyl, alkynylsulifoxy1, cycloalkylsulfoxyl, arylsulfoxyl, hetarylsulfoxyl, heterocyciylsulfoxyl, cycloalkynyl- sulfoxyl, cycloalkenylsulfoxyl, alkylsulfonyl, alkenyl- sulfonyl, alkynylsulfonyl, cycloalkylsulfonyl, aryl- sulfonyl, hetarylsulfonyl, heterocyclylsulfonyl, cyclo- alkenylsulfonyl, cycloalkynylsulfonyl, alkylsulfinyl, alkenylsulfinyl, alkynylsulfinyl, cycloalkylsulfinyl, arylsulfinyl, hetarylsulfinyl, heterocyclylsulfinyl, cycloa Ikenylsulfinyl, cycloalkynylsulfinyl, alkyl- ::carbonyloxy, alkenylcarbonyloxy, alkynylcarbonyloxy, cycloalkylcarbonyloxy, cycloalkenylcarbonyloxy, cyclo- alkynylcarbonyloxy, arylcarbonyloxy, hetarylcarbonyloxcy, heterocyclylcarbonyloxy, alkylcarbonylaiino, alkenyl- 30 carbonylamino, alkynylcarbonylamino, cycloalkylcarbonyl- amn, 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, R' and R 2 may be substituted and independently of one another are each alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl, R 3 and R 4 may be substituted by 1-4 identi- cal or different substituents R1 0 and R 3 and R 4 are each nitro, haloalkoxy, alkoxy, alkynyl; cycloalkyi, hetaryl, heterocyclyl, cycloalkenyl, cycloalkynyl, alkenyloxy, alkvnyloxy, cyc loalkoxy, hetaryloxy, heterocyc lyloxy, cycloalkenyloxy, cycloalkynyloxy, alkoximino, alkenyl- oximino, alkynyloximino, cycloalkyloximino, cycloalkenyl- oximino, cycloalkynyloximino, aryloximino, hetarylox- imino, heterocyclyloximino, cyc loalkoxycarbonyl aryloxycarbonyl, hetaryloxycarbonyl, heterocyclyloxy- carbonyl, cycloalkenyloxycarbo,.7yl, cycloalkyny"loxy- carbonyl, alkylaeminocarbonyl, dialkylaminocarbonyl, alkenylaminocarbonlyl, dialkenylaminocarbonyl, alkynyl- aminocarbonyl, dialkynylaminocarbonyl, cycloalkylamino- carbonyl, cycloalkenylaminocarbonyl, cyc loalkynyl amino- carbonyl, arylaminocarbonyl, hetarylaiinocarbonyl, ***:heterocyclylaminocarbonyl, alkylthio, alkenylthio, alkynylthio; cycloalkylthio, arylthio, hetarylthio, .:heterocyclylthio, cycloalkenylthio, cycloalkynylthio, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, arylamino, hetarylamino, heterocyc lyl amino, cycloalkenyl- :amino, cyc loalkynyl amino, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, het- arylcarbonyl, heterocyclylcarbonyl, cycloalkenylcarbonyl, VO...cycloalkynylcarbonyl, alkylsulfoxyl, alkenylsulfoxyl, .*30 alkynylsulfoxyl, cycloalkylsulfoxyl, arylsulfoxyl, hetarylsulfoxyl, heterocyclylsulfoxyl, cycloalkynyl- sulfoxyl, cycloalkenylsulfoxyl, alkylsulfonyk, 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, cyc loalkenylc arbonyl amino, cycloalkynylcarbonyl- amino, arylcarbonylamino, hetarylcarbonylamino, hetero- cyclylcarbonylamino, cycloalkylalkoxy, cycloalkenyl- alkoxy, cycloalkynylalkoxy, hetarylalkoxy, heterocyclyl- alkoxy, alkynylalkenyl, cycloalkylalkenyl, cycloalkenylalkenyl, cycloalkynylalkenyl, hetarylalkenyl, heterocyclylalkenyl, alkoxiimin'oalky1, alkenyloximinoalkyl, alkynyloximinoalkyl, cycloalkox- iminoalkyl, cycloalkenyloximinoalkyl, cycloalkynylox- iminoalkyl, aryloximinoalkyl, hetaryloximinoalkyl, heterocyclyloximinoalkyl, alkoximinoalkenyl, alkenylox- iminoalkenyl, alkynyloximinoalkenyl, cycloalkoximino- alkenyl, cycloalkenyloximinoalkenyl, cycloalkynyloximino- alkenyl, aryloximinoalkenyl, hetafTyloximinoalkenyll or heterocyclyloximinoalkenyl, R 5 R 7 and R 8 may be substituted by 1-4 identical or *5 7 .:dif ferent. substituents R10u, and R I R6, R' and Rj are each nitro, haloalkyl, alkyl, haloalkoxy, alkenyl, alkynyl, cycloalkyl, aryl, hetaryl, heterocyclyl, cycloalkenyl, cycloalkynyl, alkoxy, alkenyloxy, alkynyiloxy, cyclo- alkoxy, aryloxy, hetaxyloxy, hiterocyc lyloxy, cy,.lo1- alkenyloxyl, cycloalkynyloxy, alkoximino, alkenyloximino, alkynyloximino, cycloalkyloximino, cycloalkenyloximino, 30 cycloalkynyloximino, aryloximino, hataryloximino, hetero- cyclyloximino, cycloalkoxycarbonyl, aryloxycarbonyl, het- 4M~ aryloxycarbonyl, heterocyclyoxycarbonyl, cycloalkenyloxy- carbonyl, cycloalkynyloxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkenylaminocarbonyl, dialkenyl- aminocarbonyl, alkynylaminocarbonyl, dialkynylamino- carbonyl, cycloalkcylaminocarbonyl, cycloalkenylamino- carbonyl, cycloalkcynylaminocarbonyl, arylaminocarbonyl, 'II t 99 0050/43411 hetarylaminocarbonyl, heterocyclylaminocarbonyl, alkyl- thio, alkenylthio, alkynylthio, cycloalkylthio, a7-ylthio, hetaryithio, heterocyclylthio, cycloalkenylthio, cyclo- a1kynylthio, aikylamino, alkenylamino, alkynylamino, cyc loalkyl amino, arylamino, hetarylamino, heterocyclyl- amino, cycloalkenylanino, cycloalkynylamino, alkylcarbon- yl, alkenyi~carbonyl, alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, hetarylcarbonyl, heterocyclylcarbonyl, cycloalkenylcarbonyl, cycloalkynylcarbonyl, alkylsuif ox- J yl, alkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl, arylsulfoxyl, hetarylsulfoxyl, heterocyrclylsulfoxyl, cycloalkynylsulfoxyl, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, cycloalkyloulfonyl, arylsulfonyl, hetarylsulfonyl, heterocyclylsulfonyl, cycloalkeny-- sulfonyl, cycloalkynylsulfonyl, alkylsulfinyl, alkenyl- sulfinyl, alkynylsulfinyl, cycloalkylsulfinyl, aryl- sulfinyl, hetarylsulfinyl, 12eterocyclylsulfinyl, cyclo- alkenylsulfinyl, cycloalkynyisulfinyl, alkylcarbonyloxy, alkenylcarbonyloxy, alkyriylcarbonyloxy, cycloalkylcarbon- go yloxy, cycloalkenylcarbanyloxy, cycloalkynylcarbonyloxy, *0arycarbonyloxy, hetarylcarbonyloxy, heterocyclylcarbon- yloxy, alkylcarbonylaiaino, alkenylcarbonyl amino, alkynyl 0*carbonylamino, cyc lcalkylc arbonyl amino, cycJ.oalkenyl- carbon-k-mino, cycloalkynylcarbonylamino, arylcarbonyl- amino, ietarylcarbonyl amino or heterocyclylcarbonylaiino, R 9 may be substituted by 1-4 identical or different subst-ituents R1 0 and RO 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, alkoximinci, alkenyloximino, alkynyloximino, cycloal':loximino, cyclocoalkenyloximino, cycloalkyny.L'oximino, aryloximino, hetaryloximino, hetero- cyclyloximino, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarh7onyl, 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, alkenyithic, alkynylthio, cycloalkylthio, arylthio, hetarylthio, heterocyclylthio, cycloalkenylthio, cyclo- alkynylthio, alkylamino, alkenylainino, alkynylamino, cyc loalkyl amino, arylamino, hetarylamino, heterocyclyl- amino, cycloalkenylanin.;, cycloalkynylamino, alkylcarbon- yl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, hetarylcarbonyl, heterocyclylcarbony)., cycloalkenylcarbonyl, cycloalkynylcarbonyl, alkylsulfox- yl, alkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl, arylsulfoxyl, hetarylsulfoxyl, heterocyclylsulfoxyl, cycloalkynylsulfoxyl, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, cycloalkylsuJf'onyl, arylsulfonyl, hetarylsulfonyl, heterocyclylsulfonyl, cycloalkenyl- sulfonyl, cycloalkynylsulfonyl, alkylsulfinyl, alkenyl- sulfinyl, alkynylsulfinyl, cycloalkylsulfinyl, aryl- sulfinyl, hetarylsulfinyl, heterocyclylsulfinyl, cyclo- alkenylsulfinyl, cycloalkynylsulfinyl, alkylcarbonyloxy, alkenylcarbonyloxy, alkynylcarbonyloxy, cycloalkylcarbon- yloxy, cycloa±Jceny.lcarbonyloxy, cycloalicynylcarbonyloxy, arylc arbonyloxy, hetaryic arbonyloxy, heterocyc lyic arbon- yloxy, alkylcarbonylamino, alkenylcarbonylamino, alkynyl- cycloalkylcarbonylamino, cycloalkenyl- carbonylamino, cycloalkynylcarbonylamino, arylcarbonyl- amno hetarylcarbonylamino, heterocyclylcarbonylamino, cycloalkylalkoxy, cycloalkenylalkoxy, cycloalkynylalkoxy, arylalkoxy, hetarylalkoxy or heterocyclylalkoxy, R1 0 may be substituted by 1-4 identical or different substituents R' 1 and R1 0 is hydrogen, halogen, cyano, nitro, haloalkyl, alkyl, haloalkoxy, alkenyl, alkynyl. cycloalkyl, aryl, hetaryl, heterocyclyl, cycloalkenyl, 101 01 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- aniinocarbonyl, dialkylaminocarbonyl, alkenylamino- carbonyl, dialkenylaniinocarbonyl, alkynylarninocarbonyl, dialkynylaminocarbonyl, cycloalkylaminocarbonyl, cycloalkenylaminocarbonyl, cycloalkynylaniinocarbonyl, arylaminocarbonyl, hetarylaminocarbonyl, heterocyclylaminocarbonyl, alkylthio, alkenylthio, alkynylthio, cycloalkylthio, arylthio, hetarylthio, heterocyclylthio, cycloalkenylthio, cycloalkynyithic, alkylamino, alkenylamino, alkynylamino, cycloalkylaiino, arylamino, hetarylamino, heterocyclylamino, cycloalkenylamino, cycloalkynylamino, alkylcarbonyl, .*alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, *arylcarbonyl, hetarylcarbonyl, heterocyclylcarbonyl, cycloalkenylcarbonyl, cycloalkynylcarbonyl, alkylsuif ox- yl, alkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl, arylsulfoxyl, hetarylsulfoxyl, heterocyclylsulfoxyl, cycloalkynylsulfoxyl, cycloalkenylsulfoxyl, ::.alkylsulfonyl, alkenylsulfonyl, alkynylsulfony'l, cycloalkylsulfonyl, arylsulfonyl, hetarylsulfonyl, heterocyclylsulfonyl, cycloalkenylsulfonyl, ;30 cylcoalkynylsulfonyl, alkylsulfinyl, alkenylsulfinyl, alkynylsulfinyl, cycloalkylsulfinyl, arylsulfinyl, vp:hetarylsulfinyl, heterocyclylsulfinyl, cycloalkenyl- .*sulfinyl, cycloalkynylsulfinyl, alkylcarbonyloxy, alkenylcarbonyloxy, alkynylcarbonyloxy, cycloalkylcarbon- yloxy, cycloalkenylcarbonyloxy, cycloalkynylcarbonyloxy, aryic arbonyloxy, hetaryic arbo-nyloxy, heterocyc lyic arbon- yloxy, alkylcarbonylamino, alkenylc arbonyl amino, alkynyl- I I 102 O.Z. 0050/43411 carbonylamino, cycloalkylcarbonylamino, cycloalkenyl- carbonylamino, cyc loalkynylcarbonyl amino, ary'l-arbonyl- amino, hetarylcarbonylamino, heterocyclylcarbonylamino, cycloalkylalkoxy, cycloalkenylalkoxy, cycloalkynylalkoxy, arylalkoxy, hetarylalkoxy or heterocyclylalkoxy, R' 1 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, cyclealkenyloximino, 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, arylcabonyl hetarylcarbonyl, heterocyclylcarbonyl, cycloalkenylcarbonyl, cycloalkynylcarbonyl, alkylsulfox- yl, alkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxy1, *.:arylsulfoxyl, hetarylsulfoxyl, heterocyclylsulfoxyl, cycloalkynylsulf oxyl, cycloalkenylsulf oxyl alkylsulf onyl, alkenylsulfonyl, alkynylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, hetarylsulfonyl, heterocyclylsulfonyl, cycloalkenylsulfonyl, cycloalkynylsulfonyl, I 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 S" X Y :20 I B O OR 2 R O 2 C where B is alkyl which is substituted by 1-4 identical or different substituents R 3 alkenyl which is substituted by 1-4 identical or different substituents R 4 alkynyl 25 which is substituted by 1-4 identical or different substituents R 5 cycloalkyl which is substituted by 1-4 identical or different substituents R 6 cycloalkenyl which is substituted by 1-4 identical or different substituents R 7 cycloalkynyl which is substituted by 1-4 identical or different substituents R 8 or heterocyclyl which is I -104 O.Z. 0050/43411 substituted by 1-4 identical or different substituents R 9 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, cycloalko;,y, aryloxy, hetaryloxy, hetero- cyclyloxy, cycloalkenyloxy, cycloalkynyloxy, alkoximino, alkenyloximino, alkyriyloximino, cycloalkyloximino, cycloalkenyloximino, cycloalkynyloximino, aryloximino, hetaryloximino, heterocycyloximino, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, cycloalkyloxy- carbonyl aryloxycarbonyl, hetaryloxycarbonyl, hetero- cyclyloxycarbonyl, cycloalktuAyloxycarbonyl,, cycloalkynyl- oxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkenylaminocarbonyl, dialkenylaminocarbonyl, alkynyl- aminocarbonyl, dial kynyl aminoc arbonyl, cyc loalkyl amino carbonyl, cycloalkenylaminocarbonyl, cycloalkyn -lamino- carbonyl, arylaminocarbonyl, hetarylaminocarbonyl, heterocyclylaminocarbonyl, alkylthio, alkenylthio, alkynylthio, cycloalkylthio, arylthio, hetarylthio, heterocyclylthio, lycloalkenylthio, cycloalkynylthio, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, *arylamino, hetarylamino, heterocyclylamino, cycloalkenyl- amino, cycloalkynylamino, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, het- arylcatbonyl, heterocyclylcarbonyvl, cycloalkenylcarbonyl, *cycloalkynylcarbonyl, alkylsulfoxyl, alkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl, arylsulfoxyl, hetarylsulfoxyl, he-terocyclylsulfoxyl, cycloalkynyl- sulfoxyl, cycloalkenylsulfoxyl, alkylsulfonyl, alkenyl- sulfonyl, alkynylsulfonyl, cycloalkylsulfonyl, aryl- sulfonyl, hetarylsulfonyl, heterocyclylsulfonyl, cyclo- *.:alkenylsulfonyl, cycloalkynylsulfonyl, alkylsulfinyl, alkenylsulfinyl, alkynylsulfinyl, cycloalkylsulfinyl, 3rd arylsulfinyl, hetarylsulfinyl, heterocyclylsulfinyl, cycloalkenylsulfinyl, cycloalkynylsulfinyl, alkyl- carbonyloxy, alkenylcarbonyloxy, alkyn-ylcarbonyloxy, 105 05 0050/43411 cycloalkylcarbonyloxy, cycloalkenylcarbonyloxy, cyclo- alkynylcarbonyloxy, arylcarbortyloxy, hetarylcarbonyloxy, heterocyclylcarbonyloxy, alkylcarbonylamino, alkenyl- carbonylamino, alkynylcarbonylamino, cycloalkylcarbonyl- amino, cyc loalkenylcarbonyl amino, cycloalkynylcarbonyl- amino, arylc arbonyl amino, hetarylcarbonylamino, hetero- cyclylcarbonylamino, cycloalkylalkoxy, cycloalkenyl- alkoxy, cylcoalkynylalkoxy, arylalkoxy, hetarylalkoxy or heterocyc lylalkoxy, 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, R 1 and R 2 may be substituted and independently of one another are each alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl, R 3 and R 4 may be substituted by 1-4 identi- cal or different substituents R 10 and R 3 and R 4 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, alkylarinocarbonyl, dialkylaminocarbonyl, alkenylaminocarbonyl, dialkenylaminocarbonyl, alkynyl- aminocarbonyl, dialkynylaminocarbonyl, cycloalkylaniino- carbonyl, cycloalkenylaminocarbonyl, cyc loalkynyl amino- carbonyl, arylaminocarbonyl, hetarylaininocarbonyl, heterocyclylaminocarbonyl, alkylthio, alkenylthio, alkynylthio, cycloalkylthio, arylthio, hetarylthio, heterocyclylthio, cycloalkenylthio, cycloalkynylthio, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, arylamino, hetarylamino, heterocyclylamino, cycloalkenyl- amino, cyc loalkynyl amino, alkylcarbonyl, alkenylcarbonyl, 106 106 0050/43411 alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, het- arylcarbonyl, heterocyclylcarbonyl, cycloalkenylcarbonyl, cycloalkynylcarbonyl, alkylsulfoxyl, alkenylsulfoxyl, cycloalkyl sulfoxyl, 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, cycloalkynylf~ulfinyl, alkylcarbonyloxy, alkenylcarbonyloxy, alkynyicarbonyloxy, cycloalkylcarbon- yloxy, cycloalkenylcarbonyloxy, cycloalkynylcarbonyloxy, arylcarbonyloxy, hetarylcarbonyloxy, heterocyclylcarbon- yloxy, alkylcarbonylamino, alkenylcarbonylamino, alkynyl- carbonylamino, cycloalkylcarbonylamino, cycloalkenyl- carbonylamino, cycloalkynylcarbonylamino, arylcarbonyl- amino, hetarylc arbonyl amino, heterocyc lyl carbonyl amino, cycloalkylalkoxy, cycloalkenylalkoxy, cycloalkynylalkoxy, hetarylalkoxy, heterocyclylalkoxy, alkynylalkenyl, cyclo- alkylalkenyl, cycloalkenylalkenyl, cycloalkynylalkenyl, hetarylalkenyl, heterocyclylalkenyl, alkoximinoa'Lkyl, alkenyloximinoalkyl, alkynyloximinoalkyl, cycloalkox- iminoa.1kyl, .cycloalkenyloximinoalkyl, cycloalkynylox- iminoalkyl, aryloximinoalkyl, hetaryloximinoalkyl, .*eoycyoiinakl .loiioleyaknlx iinoalkenyl, alkynyloximinoalkenyl, cycloalkoximino- alkenyl, cycloalkenyloximinoalkenyl, cycloalkynyloximino- alkenyl, aryloximinoalkenyl, hetaryloximinoalkenyl or heterocyc lyloximinoalkenyl, R 5 R 6 R 7 and Ra may be substituted by 1-4 identical or *.:different substituents R 10 and R 5 R 6 A 7 and R 8 are each nitro, haloalkyl, alkyl, haloalkoxy, alkenyl, alkynyl, cycloalkyl, aryl, hetaryl, heterocyclyl, cycloalkenyl, cycloalkynyl, alkoxy, alkenyloxy, alkynyloxy, cyclo- alkoxy, aryloxy, hetaryloxy, heterocyclyloxy, cyclo- *1 107 O.Z. 0050/43411 dlkenyloxy, cycloalkynyloxy, alkoximino, alkenyloximino, alkynyloximino, cycloalkoximino, cycloalkenyloximino, cycloalkynyloximino, aryloximino, hetaryloxinino, hetero- cyclyloximino, cycloalkoxycarbonyl, aryloxycarbonyl, het- aryloxycarbonyl, heterocyclyoxycarbonyl, cycloalkenyloxy- carbonyl, cycloalkynyloxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkenylaminocarbonyl, dialkenyl- aniinocarbonyl, alkynylaminocarbonyl, dialkynylamino- carbontyl, cycloalkylaminocarbonyl, cycloalkenylanino- carbonyl, cycloalkynylaminocarbonyl,, arylaminocarbonyl, hetarylaminocarbonyl, heterocyclylaminocarbonyl, alkyl- thic, alkenylthio, alkynyithia, cycloalkylthio, arylthio, hetarylthio, heterocyclylthio, cycloalkenylthio, cyclo- alkynylthio, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, arylamino, hetarylamino, heterocyclyl- amino, cyc loalkenyl amino, cycloalkynylaniino, alkylcarbon- yl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, hetarylcarbonyl, heterocyclylcarbonyl, cycloalkenylcarbonyl, cycloalkynylcarbonyl, alkylsuif ox- yl, alkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl, *.:arylsulfoxyl, hetarylsulfoxyl, heterocyclylsulfoxyl, cycloalkynylsulfoxyl, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, hetarylsulfonyl, heterocyclylsulfonyl, cycloalkenyl- sulfonyl, cycloalkynylsulfonyl, alkylsulfinyl, alkenyl- sulfin'yl, alkynylsulfinyl, cycloalkylsulfinyl, aryl- sulfinyl, hetarylsulfinyl, heterocyclylsulfi4nyl, cyclo- alkenylsulfinyl, cycloalkynylsulfinyl, alkylcarbonyloxy, alkenylcarbonyloxy, alkynylcarbonyloxy, cycloalkylcarbon- yloxy, cycloalkenylcarbonyloxy, cycloalkynylcarbonyloxy, arylcarbonyloxy, hetarylcarbonyloxy, heterocyclylcarbon- yloxy, alkylcarbonylanino, alkenylcarbonylamino, alkynyl- .:carbonylamino, cycloalkylcarbonylamino, cycloalkenyl- carbonylamino, cycloalkynylcarbonylamino, arylcarbonyl- amino, hetarylcarbonylamino or heterocyc lylc arbonyl amino, Rmay be substituted by 1-4 identical or different substituents R 10 and R 9 is hydrogen, halogen, cyano, .I -108-- O.Z. 0050/43411 riitro, 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, aryloxk'mino, hetaryloximino, hetero- cyclyloximino, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxyxarbonyl, cycloalkoyycarbonyl, aryloxycarbonyl, hetaryloxycarbonyl., heterocyclyloxycarbonyl, cycloalkenyloxycarbonyl, cycloalkynyloxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkenylaminocarbonyl, dialkenylaminocarbonyl, alkynylamirnocarbonyl, dialkynylaminocarbonyl, cycloalkyla~ninocarbony1, cycloalkenylaininocarbonyl, cycloalkynylaminocarbonyl, arylaminocarbonyl, hetarylaminocarbonyl, heterocyclylaminocarbonyl, alkyl. thio, alkenylthio, alkynylthio, cycloalkylthio, arylthio, hetarylthio, heterocyclylthio, cycloalkenylthio, cyclo- alkyriylthio, alkylamino, alkenylemino, alkynylamino, cyc loalkylamino, arylamino, hetarylamino, heterocyc lyl- amino, cyclo&lkenylamino, cyc loalkynyl amino, alkylcarbon- yl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, hetarylcarbonyl, heterocyclylcarbonyl, cycloalkenylcarbonyl, cycloalkynylcarbonyl, alkylsuif ox- yl, alkenylsulfoxyl, alkynyls~ulfoxyl, cycloalkylsulfoxyl, arylsulfoxyl, hetarylsulfoxyl, heterocyclylsulfoxyl, cycloalkynljrlsulfoxy1, cycloalkenylsulfoxyl, alkylsulfonyl,, alkenylsulfonyl, alkynylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, hetarylsulfonyl, heterocyclylsulfonyl, cycloalkenylsulfonyl, cycloalkynylsulfoc~y1, alkylsulfinyl, alkenylsulfinyl, .*alkynylsulfinyl, cycloalkylsulfinyl, arylsulfinyl, hetarylsulfinyl, heterocyclylsulfinyl, cycloalkenyl- sulfinyl, cycloalkynylsulfinyl, alkylcarbonyloxy, alkenylcarbonyloxy, alkynylcarbonyloxy, cycloalkylcarbon- yloxy, cycloalkenylcarbonyloxy, cycloalkynylcarbonyloxy, 'S 109 O.Z. 0050/43411 aryic arbonyloxy, hetaryic arbonyloxy, heterocyc lyic arbon- yloxy, alkylcarbonylamino, alkenylc arbonyl amino, alkynyl- carbonylamino, cycloalkylcarbonylamino, cycloalkenyl- carbonylamino, cycloalkynylcarbonylamino, arylcarbonyl- amino, hetarylc arbonyl amino, heterocyclyicarbonylamino, cycloalkylalkoxyj, cycloalkenylalkoxy, cycloalkynylalkoxy, arylalkoxy, hetarylalkoxy or heterocyclylalkoxy, Rio may be substituted by 1-4 identical or different substituents Rill and Rio is hydrogen, halogen, cyano, nitro, haloalkyl, alkyl, haloalkoxy, alkenyl, alkynyl, cycloalkyl, aryl, hetaryl, heterocyclyl, cycloalkenyl, cycloalkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalk- oxy, aryloxy, hetarylox,.y, heterocyclyloxy, cycloalkenyl- oxy, cycloalkynyloxty, alkoximino, a'ikenyloximino, alkynyloximino, cyc loalkyloximino, cyclocoalkenyloximino, cycloalkynyloximino, aryloximino, hetaryloximino, hetero- cyclyloximino, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, cycloalkoxycarbonyl, aryloxycaxw'onyl, hetaryloxycarbonyl, heterocyclyloxycarbonyl, cycloalkenyloxycarbonyl, cycloalkynyloxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aleyaioabnl *.leyl-.ncabnl alkenylaminocarbonyl, dialkynyla:.inocarbonyl, 0. cylaklmncroy, ccoleyaioabnl iayylaminocarbonyl, hetarylaminocarbonyl, heterocyclylaminocarbonyl, alkyl- 0. thio, alkenyithic, alkynylthio, cycloalkylthio, arylthio, hetarylthio, heterocyclylthio, cycloalkenylthio, cyclo- 30 alkynylthio, alkylamino, alkenylamino, alkynylanino, *00 3 cycloalkylamino, arylamino, hetarylamino, heterocyclyl- a ino cyc loalkenyl amino, cyc loalkynyl amino, alikylcarbon- yl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, to., arylcarbonyl, hetarylcarbonyl, heterocyclylcarbonyl, cycloalkenylcarbonyl, cycloalkynylcarbonyl, alkylsuif ox- yl, alkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl, arylsulfoxyl, hetarylsulfoxyl, heterocyclyisulfoxyl, cycloalkynylsulfoxyl, cycloalkenylsulfoxyl,
111-1- tv -110 O.Z. 0050/43411 alkylsulfonyL, alkenylsulfonyl, alkynylsulfonyl, cycloalkylsulfonyl, airylsulfonyl, hetarylsulfonyl, heterocyclylsulfonyl, cycloalkenylsulfonyl, cycloalkynyisulfonyl, alkylsulfinyl, alkenylsulfinyl, alkynylsulfinyl, cycloalkylsulfinyl, arylsulfinyl, hetarylsulfinyl, heterocyclylsulfinyl, cycloalkenyl- sulfinyl, cycloalkynylsulfinyl, alkylcarbonyloxy, alkenylcarbonyloxy, alkyny'lcarbonyloxy, cycloalkylcarbon- yloxy, cycloalkenylcarbonyloxy, cycloalkynyicarbonyloxy, arylcarbonyloxy, hetarylcarbonyloxy, heterocyclylcarbon- yloxy, alkylcarbonylamino, alkenylcarbonyl amino, alkynyl- carbonylardino, cycloalkylcarbonylamino, cycloalkenyl- carbonylamino, cycloalkynylcarbonylamino, arylcarbonyl- amino, hetarylcarbonylamino, heterocyclylcarbonylamino, cycloalkylalkoxy, cycloalken-ylalkoxy, cycloalkynylalkoxy, arylalkoxy, hetarylalkoxy or heterocyclylalkoxy, R" may be substituted and is hydrogen, halogen, cyano, nitro, haloalkyl, alkyl, haloalkoxy, alkenyl, alkynyl, cycloalkyl, aryl, hetaryl, heterocyclyl, cycloalkenyl, cycloalkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalk- aryloxy, hetaryloxy, heterocyclyloxy, cycloalkenyl- oxy, cycloalkynyloxy, alkoximino, alkenyloximino, Calkynyloximino, cycloalkoximino, cycloalkenyloximino, cycloalkynyloximino, aryloximino, hetaryloximino, hetero- cyclyloximino, alkoxycarbonyl, alkenylcarbonyl, alkynyloxycarbonyl, cycloalkoxycarbonyl, aryloxycarbonyl, hetaryloxycarbonyl, heterocyclyloxycarbony1, cycloalkenyloxycarbonyl, cycloalkynyloxycarbonyl, alyaioabnl dilklmiocronl alkeylaminocarbonyl, dialkeylaminocarbonyl, alkenylami4nocarbonyl, dialkenylaminocarbonyl, cyalkylaminocarbonyl, diclalknylaminocarbonyl, cycloalkylaminocarbonyl, cylakylaminocarbonyl, hetairylaminocarbonyl, heterocyclylaniinocarbonyl, alkyl- thio, alkenylthio, alkynylthio, cycloalkylthio, arylthio, hetarylthio, heterocyclylthio, cycloalkenylthio, cyc alkynylthio, alkylamino, alkenylamino, alkynylamino, 111 C.Z. 0050/43411 cyc loalkyl amino, arylamino, hetaryl amino, heterocyc lyl- amino, cycloalkenylamino, cyc loalkynyl amino, alkylcarbon- yl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, hetary'Lcarbonyl, heterocyclylcarbonyl, cycloalkenylcarbonyl, cycloalky-nylcarbonyl, alkylsulfox- yl, alkenylsulfoxyl, alkynylsulfoxyl, cycloalkylsulfoxyl, arylsulfoxyl, hetarylsulfoxyl, hoterocyclylsulfoxyl, cycloalkynylsulfoxyl, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, cycloalkylsulfonyl, arylsulfonyl, hetarylsulfonyl, heterocyclylsulfonyl, cycloalkenyl- sulfonyl, cycloalkynylsulfonyl, alkylsulfinyl, alkenyl- sulfinyl, alkynylsulfinyl, cycloalkylsulfinyl, aryl- sulfinyl, hetarylsulfinyl, heterocyclylsulfinyl, cyclo- alkenylsulfinyl, cycloalkynylsulfinyl, alkyls-ulfinyl, alkenylsulfinyl, alkynylsulfinyl, cycloalkylsulfinyl, arylsulfinyl, hetarlsulfinyl, heterocyclylsulfinyl, cycloalkenylsulfinyl, cycloalkynylsuifinyl, alkyl- carbonyloxy, alkenylcarbonyloxy, alkynylcarbonylox-y, cycloalkylcarbonyloxy, cycloalkenylcarbonyloxy, cyclo- alkynylcarbonyloxy, arylcarbonyloxy, hetarylcarbonyloxy, alkylcarbonylaiino, alkenyl- carbonylamino, alkynylcarbonylamino, cycloalkylcarbonyl- amno cyc loalkenylc arbonyl amino, cycloalkynylcarbonyl- amno aryl carbonyl amino, hetarylcarbonyl amino, hetero- cyclylcarbonylamino, cycloalkylalkoxy, ~4*cycloalkenylalkoxy, cycloalkynylalkoxy, arylalkoxy, ~:'.hetarylalkoxy or heterocyclylalkoxy, or an acid addition product or base addition product of this compound. DATED this 22nd day of July 1993. BASF AKTIENGESELLSCHAFT 4 4 WATERMARK PATENT TRADEMARK ATTORNEYS "THE ATRIUM" 290 BURWCY3D ROAD HAwTHORN. VIC. 3122. ,BASF Aktiengjesellschaft 920400 OZ.05/41 O.Z. 0050/43411 Substituted acrylates and crop protection agents containing them ABSTRACT OF THE DISCLOSURE: Substituted acrylates ot the formula I Y 100 OR 2 R10 2 C **where: B is Substituted alkyl, substituted alkenyl, substituted alkynyl, substituted cycloalkyl, substituted cycloalkenyl, substi- tuted cycloalkynyl, or subst-ituted heterocyclyl, X and Y are identical or different and are hydrogen, halogen, cyano, nitro, haloalkyl. alkyl, haloal- 4Y~ koxy, alk~enyl, alkynyl, cycloalkyl, ary! hetaryl, heterocy- clyl, cycloalkenyl, cycloalkinyl, alkoxy, alkenyloxy, al)7hy-- nyloxy, cycloalkyloxy, aryloxy, heteryloxy, 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- ky'laininocarbonyl, alkenylaminocarbonyl, dialkenylaminocarbo- nyl, alkynylaminocarbonyl, dialkynylaminocarbonyl, cycloal- kllaminocarbonyl, cycloalkenylaminocarbonyl, cycloalkynyla- minocarbonyl, arylaminocarbonyl, hetarylaminocarbonyl, het- erocyclylaminocarbonyl, alkylthio, alkenylthio, alkynylthio, BASF Aktiengesae11Bchaft 920400 O.Z. 0050/43411 cycloalkylthio, arylthio, hetarylthio, heterocyclyithia, cy- cloalkenyithia, cycloalkynyl-jhio, alkylamino, alkenylamino, alkynylamiro, cycloalkylamino, arylamino, hetarylam--'no, bet- erocyclylamino, cycloalkenylanino, cycloalkynylamino, alkyl- carbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbo- nyl, arylcarbonyl, hetarylcarbonyl, heterocyclylcarbonyl, cycloalkenylcarbonyl, cycloalkynylcarbonyl, allcylsu1 foxyl, alkenylsulfoxyl, alkynylsuifoxyl, cycloalkylsulfoxyl, aiyl- si11foxyl, hetarylsulfoxyl, heterocyclylsulfoxyl, cycloalky- nylsulfoxyl, cycloalkenylsulfoxyl, alkylsulfonyl, alkenyl- sulfonyl, alkynylsulfonyl, cycloalkylsulfonyl, arylsiulfonyl, hetarylsulfonyl, heterocyclylsulfonyl, cycloalkeny) sulfornyl, cycloalkynylsulfonyl, aJ.kyl~ulfinyl, alkenylsulfinyl, alky- nylsulfinyl, cycloalkylsulfinyl, arylsulfinyl, hetarylsulfi- 15 nyl, heterocyclylsulfinyl, "--cloalkenylsulfinyl, cycloalky- nylsulfinyl, alkyJlcarbonyloxy, alkenylcarbonyloxy, alkynyl- carbonyloxy, cycloalkylcarbonyloxy, cycloalkenylcarbonylox-y, :cycloal. ,ynylcarbonyloxy, arylcarbonyloxy, hetarylcarbony- loxy, heterocyclylcarbonyloxy, alkylcarbonylamino, alkenyl- carbonylaminc, alkynylcarbonylamino, cycloalkylcarbonyla- mino, cycloalkenylcarbonylamino, cycloalkynylcarbonylamino, kynylalkyloxy, arylalkyloxy, hetarylalkyloxy or he-erocycly- lalkyloxy, and R 1 and RI- are alkyl, alkenyl, alkynyl, cycloalkyl or cy- c-loalkenyl, and acid addition products and base addition products of such compounds, and fungicides containing these 30 compounds.
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DE4313267A1 (en) * 1993-04-23 1994-10-27 Basf Ag Diaryl derivatives and their use as crop protection agents
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US6777491B1 (en) 1997-04-23 2004-08-17 Mitsui Chemicals, Inc. Multilayered article, vessel and resin composition based on polyethylene
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WO2003099793A1 (en) * 2002-05-24 2003-12-04 Takeda Pharmaceutical Company Limited 1,2-azole derivatives with hypoglycemic and hypolipidemic activity
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WO2016144936A1 (en) 2015-03-09 2016-09-15 Bristol-Myers Squibb Company Lactams as inhibitors of rock
US11919871B1 (en) * 2023-11-02 2024-03-05 King Faisal University 3-(3-chlorophenyl)-5-((2-isopropyl-5- methylphenoxy)methyl)-1,2,4-oxadiazole as an anti-cancer and antimicrobial compound

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0415569A2 (en) * 1989-09-01 1991-03-06 Zeneca Limited Agrochemical compositions
EP0178826B1 (en) * 1984-10-19 1991-12-18 Zeneca Limited Fungicides
EP0614607A1 (en) * 1993-03-11 1994-09-14 Zeneca Limited Herbicidal composition

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0178826B1 (en) * 1984-10-19 1991-12-18 Zeneca Limited Fungicides
EP0415569A2 (en) * 1989-09-01 1991-03-06 Zeneca Limited Agrochemical compositions
EP0614607A1 (en) * 1993-03-11 1994-09-14 Zeneca Limited Herbicidal composition

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