CH689421A5 - Zwischenprodukte für Oximäther. - Google Patents

Zwischenprodukte für Oximäther. Download PDF

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Publication number
CH689421A5
CH689421A5 CH01208/91A CH120891A CH689421A5 CH 689421 A5 CH689421 A5 CH 689421A5 CH 01208/91 A CH01208/91 A CH 01208/91A CH 120891 A CH120891 A CH 120891A CH 689421 A5 CH689421 A5 CH 689421A5
Authority
CH
Switzerland
Prior art keywords
alkyl
formula
compounds
methyl
phenyl
Prior art date
Application number
CH01208/91A
Other languages
English (en)
Inventor
Hans Peter Dr Isenring
Original Assignee
Novartis Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Novartis Ag filed Critical Novartis Ag
Priority to CH01208/91A priority Critical patent/CH689421A5/de
Priority to PH42549A priority patent/PH11991042549B1/en
Priority to NZ238346A priority patent/NZ238346A/en
Priority to DK98115073T priority patent/DK0893434T3/da
Priority to IL9834191A priority patent/IL98341A/en
Priority to DE59109146T priority patent/DE59109146D1/de
Priority to EP91109035A priority patent/EP0460575B1/de
Priority to DE59108191T priority patent/DE59108191D1/de
Priority to AT95112791T priority patent/ATE182880T1/de
Priority to CA002043733A priority patent/CA2043733C/en
Priority to EP98115073A priority patent/EP0893434B1/de
Priority to ES91109035T priority patent/ES2091834T3/es
Priority to AT91109035T priority patent/ATE143003T1/de
Priority to ES98115073T priority patent/ES2192722T3/es
Priority to ES95112791T priority patent/ES2137421T3/es
Priority to DK95112791T priority patent/DK0694529T3/da
Priority to DK91109035.5T priority patent/DK0460575T3/da
Priority to AT98115073T priority patent/ATE233236T1/de
Priority to PT97848A priority patent/PT97848B/pt
Priority to EP95112791A priority patent/EP0694529B1/de
Priority to EP95112790A priority patent/EP0703215A1/de
Priority to AR91319853A priority patent/AR247725A1/es
Priority to SG1996001100A priority patent/SG42939A1/en
Priority to DE59109247T priority patent/DE59109247D1/de
Priority to PL91290533A priority patent/PL168218B1/pl
Priority to HU0000906A priority patent/HU0000906D0/hu
Priority to BR919102305A priority patent/BR9102305A/pt
Priority to HU871/91A priority patent/HU218303B/hu
Priority to IE20010092A priority patent/IE83646B1/en
Priority to IE189991A priority patent/IE80848B1/en
Priority to SK1688-91A priority patent/SK278282B6/sk
Priority to KR1019910009225A priority patent/KR0172948B1/ko
Priority to CS911688A priority patent/CZ279709B6/cs
Priority to AU78167/91A priority patent/AU633735C/en
Priority to IE970618A priority patent/IE83213B1/en
Priority to SU914895703A priority patent/RU2077527C1/ru
Priority to JP3160979A priority patent/JP3000240B2/ja
Priority to LVP-93-420A priority patent/LV10609B/en
Priority to US08/114,991 priority patent/US6407100B1/en
Priority to MD94-0259A priority patent/MD1025C2/ro
Priority to US08/483,727 priority patent/US6355634B1/en
Priority to IL11848696A priority patent/IL118486A0/xx
Priority to GR960402334T priority patent/GR3021080T3/el
Priority to HK98104803A priority patent/HK1005721A1/xx
Publication of CH689421A5 publication Critical patent/CH689421A5/de
Priority to GR990402732T priority patent/GR3031643T3/el
Priority to LU90620C priority patent/LU90620I2/fr
Priority to NL350004C priority patent/NL350004I2/nl

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    • 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
    • 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
    • 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
    • A01N37/44—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 nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/50—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 nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
    • 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
    • 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
    • A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
    • A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
    • A01N43/30—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
    • C07C251/60—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/11—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound oxygen atoms bound to the same saturated acyclic carbon skeleton
    • C07C255/13—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound oxygen atoms bound to the same saturated acyclic carbon skeleton containing cyano groups and etherified hydroxy groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/63—Carboxylic acid nitriles containing cyano groups and nitrogen atoms further bound to other hetero atoms, other than oxygen atoms of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C255/64—Carboxylic acid nitriles containing cyano groups and nitrogen atoms further bound to other hetero atoms, other than oxygen atoms of nitro or nitroso groups, bound to the same carbon skeleton with the nitrogen atoms further bound to oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/56—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • 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
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/53—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
    • C07D279/12—1,4-Thiazines; Hydrogenated 1,4-thiazines not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans 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 carbon atoms of the hetero ring
    • C07D307/83—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans 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 carbon atoms of the hetero ring
    • C07D307/84—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
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    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings 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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    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
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    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/58—Radicals substituted by nitrogen atoms
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    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring 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 atoms of the carbocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring 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 atoms of the carbocyclic ring
    • C07D317/64—Oxygen atoms
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    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
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    • C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
    • C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
    • C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D319/18—Ethylenedioxybenzenes, not substituted on the hetero ring
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Description


  
 



  Die vorliegende Erfindung betrifft Zwischenprodukte für Oximäther der allgemeinen Formel 
EMI1.1
 
 



  worin
 R1 C1-4-Alkyl bedeutet,
 (Y-X) C1-2-alkyl-ON= bedeutet und
 Z für eine Aldimino- oder Ketiminogruppe steht, und zwar insbesondere für eine Gruppe 
EMI1.2
 
 



  worin 
 R2 Wasserstoff, C1-4-Alkyl, C1-4-Halogenalkyl, C3-6-Cycloalkyl, C2-4-Alkenyl, C2-4-Alkinyl, C1-2-Alkoxymethyl, C1-2-Alkylthiomethyl, C1-4-Alkylsulfonyl, C1-3-Alkoxy, C1-3-Alkylthio oder Cyano und 
 R3 C1-6-Alkyl, Aryl-C1-4-alkyl, Heteroaryl-C1-4-alkyl, C2-12-Alkenyl, Aryl-C2-4-alkenyl, Aryloxy-C1-4-alkyl, Heteroaryloxy-C1-4-alkyl, Heteroaryl-C2-4-alkenyl, C3-6-Cycloalkyl, Aryl, Heteroaryl, C2-5-Alkanoyl, Aroyl oder Heteroaroyl bedeuten, oder
 R2 und R3 zusammen mit dem Kohlenstoffatom, an das sie gebunden sind, einen gegebenenfalls substituierten, gegebenenfalls ein Sauerstoffatom, Schwefelatom und/oder Stickstoffatom enthaltenden vier- bis siebengliedrigen gesättigten oder ungesättigten Ring bilden, der zudem einen gegebenenfalls substituierten ankondensierten Benzolring aufweisen kann. 



  Die Verbindungen der Formel I, worin (Y-X) ausserdem CH2=, C1-2-Alkylthio-C= bedeuten können, entsprechend dem EP-B 460 575, besitzen fungizide Eigenschaften und eignen sich als fungizide Wirkstoffe, insbesondere zur Verwendung in der Landwirtschaft und im Gartenbau. 



  In der obigen Formel 1 und im folgenden können sämtliche Gruppen "Alkyl" und "Alkenyl", als solche oder als Teil grösserer Gruppen, z.B. Heteroarylalkyl, je nach Anzahl der Kohlenstoffatome geradkettig oder verzweigt sein. Zudem können die Alkenylgruppen eine oder mehrere Doppelbindungen aufweisen. Halogen als Substituent bedeutet Fluor, Chlor, Brom oder Jod, wobei Fluor, Chlor und Brom bevorzugt sind. Eine Halogenalkylgruppe kann einen oder mehrere gleiche oder verschiedene Halogensubstituenten aufweisen. Unter Aryl ist insbesondere Phenyl, Naphthyl, Phenanthryl oder Fluorenyl zu verstehen. Heteroaryl bedeutet eine heterocyclische Gruppe mit aromatischem Charakter und 1-3 Heteroatomen N, O und/oder S. Bevorzugt sind Triazol oder andere Fünfringe und Sechsringe mit 1-2 Heteroatomen, die ihrerseits zusätzlich einen oder zwei ankondensierte Benzolringe besitzen können. 



  Als Beispiele, die keine limitierende Bedeutung besitzen, die aber vereinfachend im folgenden als "Gruppe Het*" bezeichnet werden sollen, seien Pyrrolyl, Pyridyl, Furyl, Thienyl, Isoxazolyl, Thiazolyl, Pyrazinyl, Pyridazinyl, Imidazolyl, Pyrimidinyl oder Triazolyl, oder eine solche Gruppe mit ankondensiertem Benzol, z.B. Chinolinyl, Chinoxalinyl, Benzofuryl, Benzothienyl oder Dibenzofuryl genannt. Sinngemäss gilt dies auch für "Aryl" oder "Heteroaryl" als Teil einer grösseren Gruppe, z.B. Aralkyl bzw. Heteroarylalkyl. Die Aryl- und Heteroarylgruppen können jeweils einen oder mehrere der folgenden Substituenten aufweisen: 



  Halogen, C1-4-Alkyl, C1-4-Halogenalkyl, Aryl-C1-4-alkyl, Aryloxy-C1-4-alkyl, C2-4-Alkenyl, Aryl-C2-4-alkenyl, C2-4-Alkinyl, C3-6-Cycloalkyl, Aryl, C1-4-Alkoxy, C1-4-Halogenalkoxy, Aryl-C1-4-alkoxy, C1-4-Alkylthio, Aryloxy, Cyano, Nitro, C2-4-Halogenalkenyl, C2-4-Halogenalkinyl, C2-4-Alkenyloxy, C2-4-Halogenalkenyloxy, C3-4-Alkinyloxy, C3-4-Halogenalkinyloxy, Cyclopropylmethoxy, Cyclopropyl (gegebenenfalls ein- bis dreifach substituiert durch Halogen und/oder Methyl), Cyanomethoxy (-OCH2CN), C1-4-Alkoxymethyl, C1-4-Alkylthiomethyl, C1-4-Alkylsulfinylmethyl, C1-4-Alkyl sulfonylmethyl, Arylthio, Thiocyanato, C1-4-Alkoxyiminomethyl, C1-4-Alkanoyloxy, C1-4-Alkoxycarbonyl; 



  sowie auch einen Heteroarylrest, einen Heteroaryl-C1-4-alkylrest, einen HeteroaryIoxy-C1-4-alkylrest, einen Heteroaryl-C2-4-alkenylrest, einen Heteroaryl-C1-4-alkoxyrest oder einen Heteroaryloxyrest; wobei hierin unter dem Begriff Heteroaryl ein Vertreter der obengenannten "Gruppe Het*" zu verstehen ist. 



  Fast alle der für Aryl- und Heteroarylgruppen vorgenannten Substituenten können ein- bis zweimal auftreten, bevorzugt einmal, mit Ausnahme von C1-4-Alkyl, das bis zu vierfach als Substituent in Frage kommt, und Halogen, das bis zu dreifach, im Falle von Fluor auch bis zu fünffach vorkommen kann. 



  Der bevorzugte Arylrest ist Phenyl, gleichgültig, ob er allein oder als Teil eines anderen Substituenten in Erscheinung tritt. Aroyl ist demgemäss bevorzugt Benzoyl. 



  C2-Alkanoyl bedeutet Acetyl. Unter Halogenalkyl sind Alkylgruppen zu verstehen, die bis zu sechsfach gleich oder verschieden durch F, Cl, Br und/oder J substituiert sind. Beispiele von Halogenalkylgruppen allein oder als Teil eines anderen Substituenten (wie Halogenalkoxy) sind CH2Cl, CHCl2, CCl3, CHBr2, CH2CH2Cl, CHCI-CHCl2, CF2Cl, CH2J, CF3, C2F5, CF2-CF2Cl, CHF2, CH2F, CF2CHFCF3. 



  Bevorzugt sind Trifluormethyl, Difluormethoxy und Trifluormethoxy. 



  Zudem können die Arylgruppen (insbesondere Phenyl) einen ein oder zwei Sauerstoffatome aufweisenden fünf-, sechs- oder siebengliedrigen gesättigten oder ungesättigten Ring tragen, der gegebenenfalls ein- oder mehrfach mit Methyl, Methoxy, Phenyl, Halogen, Cyano oder Oxo (C=O) substituiert sein kann. Beispiele solcher Gruppen sind 5-Benzofuryl, 6-Benzodioxanyl und 5-(1,3-Benzodioxolyl). 



  Im Falle, dass R2 und R3 zusammen mit dem Kohlenstoffatom, an das sie gebunden sind, einen gegebenenfalls substituierten Ring bilden, wie dieser oben näher beschrieben ist, kommen als Substituenten des Ringes 
EMI4.1
 
 



  insbesondere C1-6-Alkyl oder gegebenenfalls substituiertes Phenyl in Frage. Auch der allfällig vorhandene ankondensierte Benzolring kann substituiert sein. Als Substituenten der Phenylgruppe bzw. des Benzolrings selber kommen die oben im Zusammenhang mit der Arylgruppe genannten in Betracht. 



  Falls in den Verbindungen der Formel 1 asymmetrische Kohlenstoffatome vorliegen, treten die Verbindungen in optisch aktiver Form auf. Allein aufgrund des Vorhandenseins der aliphatischen bzw. Imino-Doppelbindung X=C und der Imino-Doppelbindung der Aldimino- oder Ketiminogruppe Z treten die Verbindungen auf jeden Fall in der [E]- oder [Z]-Form auf. Ferner kann Atropisomerie auftreten. Die Formell soll all diese möglichen isomeren Formen sowie deren Gemische, z.B. racemische Gemische und beliebige [E/Z]-Gemische, umfassen. 



  Bei den Verbindungen der Formel I bedeutet R1 vorzugsweise Methyl; und unabhängig davon (Y-X) vorzugsweise Methylen, Methylthiomethylen (CH-SCH3) oder Methoxyimino (N-OCH3); besonders bevorzugt sind Verbindungen, worin R, Methoxyimino darstellt. 



  In der Gruppe (R2)(R3)C=N- ist R2 vorzugsweise Wasserstoff, C1-4-Alkyl (insbesondere Methyl oder Äthyl), C1-4-Halogenalkyl (insbesondere Trifluormethyl) oder C3-6-Cycloalkyl (insbesondere Cyclopropyl) und R3 ist vorzugsweise gegebenenfalls substituiertes Phenyl, Naphthyl (insbesondere  beta -Naphthyl) oder Benzyl, wobei allfällige Substituenten vorzugsweise bis drei gleiche oder verschiedene Halogenatome (insbesondere Fluor, Chlor und/oder Brom), C1-4-Alkylgruppen (insbesondere Methyl), C1-4-Halogenalkylgruppen (insbesondere Trifluormethyl), C1-4-Halogenalkoxygruppen (insbesondere Trifluor methoxy) und Alkylendioxy (insbesondere 3,4-Methylendioxy) sind, oder Heteroaryl, insbesondere gegebenenfalls mit bis zwei Methylgruppen substituiertes Furyl, gegebenenfalls mit Chlor oder Methyl substituiertes Thienyl, Pyridyl oder Benzofuryl. 



  Falls R3 Heteroaryl bedeutet, ist R2 vorzugsweise Methyl. 



  Weitere Vertreter von Verbindungen der Formel I sind:
 diejenigen Verbindungen der Formel 1, in denen R, Methyl, (Y-Z) CH2, Z eine Gruppe (R2)(R3)C=N-, R2 Methyl und R3 3-Trifluormethyl-benzyl, 4-Chlor-3trifluormethyl-benzyl, Phenyl, 3-Chlorphenyl, 3,5-Dichlorphenyl, 2-Fluor-5-methylphenyl, 3-Trifluormethoxyphenyl oder 5-Chlor-2-thienyl bedeuten; 



  Das Verfahren zur Herstellung der Verbindungen der Formel 1 ist dadurch gekennzeichnet, dass man ein Oxim Z-OH, insbesondere ein Oxim der allgemeinen Formel 
EMI5.1
 
 



  worin R2 und R3 die oben angegebenen Bedeutungen besitzen, mit einem Benzylalkoholderivat der allgemeinen Formel 
EMI5.2
 
 



  worin R1 und Y-X die oben angegebenen Bedeutungen besitzen und U eine Abgangsgruppe bedeutet, zur Reaktion bringt. 



  Bei dieser Reaktion handelt es sich um eine nucleophile Substitution, die unter den diesbezüglich üblichen Reaktionsbedingungen durchgeführt werden kann. Unter der im Benzylalkoholderivat der Formel III vorhandenen Abgangsgruppe U ist vorzugsweise Chlor, Brom, Jod, Mesyloxy, Benzolsulfonyloxy oder Tosyloxy zu  verstehen. Die Umsetzung erfolgt zweckmässigerweise in einem inerten organischen Verdünnungsmittel, wie einem cyclischen Äther, z.B. Tetrahydrofuran oder Dioxan, Aceton, Dimethylformamid oder Dimethylsulfoxid, in Gegenwart einer Base, wie Natriumhydrid, Natrium- oder Kaliumcarbonat, eines tertiären Amins, z.B. eines Trialkylamins, insbesondere Diazabicyclononan oder Diazabicycloundecan, oder Silberoxid, bei Temperaturen zwischen -20 DEG C und 80 DEG C, vorzugsweise im Temperaturbereich von 0 DEG C bis 20 DEG C. 



  Als Alternative kann die Umsetzung unter Phasentransferkatalyse in einem organischen Lösungsmittel, wie beispielsweise Methylenchlorid, in Gegenwart einer wässrigen basischen Lösung, z.B. Natriumhydroxidlösung, sowie eines Phasentransferkatalysators, wie beispielsweise Tetrabutylammoniumhydrogensulfat, bei Raumtemperatur erfolgen [siehe beispielsweise W.E. Keller, "Phasen-Transfer Reactions", Fluka-Compendium Vol. I und II, Georg Thieme Verlag, Stuttgart (1986/1987), in dem insbesondere Chemistry Letters 1980, Seiten 869-870, erwähnt ist]. 



  Die Isolierung und Reinigung der so hergestellten Verbindungen der Formel I kann nach an sich bekannten Methoden erfolgen. Ebenfalls nach an sich bekannten Methoden können allfällig erhaltene Isomerengemische, z.B. E/Z-Isomerengemische, in die reinen Isomeren aufgetrennt werden, beispielsweise durch Chromatographie oder fraktionierte Kristallisation. 



  Die als Ausgangsmaterialien im erfindungsgemässen Verfahren verwendeten Oxime Z-OH, z.B. der Formel II, sind entweder bekannt oder können nach an sich bekannten Methoden hergestellt werden, beispielsweise durch Umsetzung der entsprechenden Carbonylverbindung R2R3C=O mit Hydroxylaminhydrochlorid in Gegenwart einer Base, z.B. Natrium- oder Kaliumhydroxid oder Pyridin, Weitere Methoden finden sich in Houben-Weyl, "Methoden der Organischen Chemie", Band X/4, Seiten 3-308 (1968) ("Herstellung und Umwandlung von Oximen"). 



  Ebenfalls sind die Ausgangsmaterialien der Formel lll, d.h. die  alpha -(2-UCH2-phenyl)-acrylsäure-alkylester der Formel lIIa, die  alpha -(2-UCH2-phenyl)- beta -(C1-2-alkylthio) -acrylsäure-alkylester der Formel Illb sowie die 2-(2-UCH2-phenyl)-glyoxylsäure-alkylester -O-(C1-2-alkyl)oxim der Formel lllc 
EMI7.1
 
 



  entweder bekannt, oder sie können nach an sich bekannten Methoden hergestellt werden. So ist in der europäischen Patentpublikation (EP) 348 766 die Herstellung von  alpha -(2-Brommethyl-phenyl)-acrylsäure-methylester, in der EP 310 954 und in Angew. Chem. 71, 349-365 (1959) die Herstellung von  alpha -(2-Brommethyl-phenyl)- beta -methylthio-acrylsäure-methylester und in der EP 363 818 und wiederum in Angew. Chem. 71, 349-365 (1959) die Herstellung von 2-(2Brommethyl-phenyl)-glyoxylsäure-methylester-O-methyloxim beschrieben. 



  Die noch neuen Verbindungen der Formel lllc bilden den Gegenstand vorliegender Erfindung. Die Verbindung der Formel lllc worin R, Methyl, U Brom und C1-2-Alkyl Methyl bedeuten ist aus EP-A 254 426 bekannt. 



  Zur Herstellung eines  alpha -(2-Brommethyl-phenyl)- beta -methylthio-acrylsäure-C1-4-alkylesters kann man auch eine von dem  der EP 310 954 beschriebenen Verfahren abweichende Synthese verwenden, die als erste Stufe die Bromierung des entsprechenden 3-(4-Brom-benzolsulfonyloxy)-2-(o-tolyl) -acrylsäure-C1-4-alkylesters mit N-Bromsuccinimid zum 3-(4-Brom-benzolsulfonyloxy)-2-(2-brommethyl-phenyl)        -acrylsäure-C1-4-alkylester und als zweite Stufe die Umsetzung des letztgenannten Esters mit Natriummethanthiolat zum gewünschten Endprodukt umfasst. Das Ausgangsmaterial 3-(4-Brom-benzolsulfonyloxy)-2-(otolyl)-acrylsäure-methylester ist beispielsweise in der EP 310 954 beschrieben. 



  Die Verbindungen der Formel I besitzen fungizide Wirkung und können dementsprechend zur Bekämpfung bzw. Verhütung von Pilzbefall in der Landwirtschaft,  im Gartenbau sowie im Holzschutz Verwendung finden. Sie eignen sich insbesondere zur Hemmung des Wachstums oder zur Vernichtung von phytopathogenen Pilzen auf Pflanzenteilen, z.B. Blättern, Stengeln, Wurzeln, Knollen, Früchten oder Blüten, und auf Saatgut sowie von im Erdboden auftretenden Schadpilzen. Ferner können mit den Verbindungen der Formel I holzabbauende und holzverfärbende Pilze bekämpft werden. Die Verbindungen der Formel I sind beispielsweise wirksam bei der Bekämpfung von Pilzen der Klassen Deuteromycetes, Ascomycetes, Basidiomycetes und Phycomycetes. 



  Besonders eignen sich die Verbindungen der Formel I zur Bekämpfung der folgenden Schaderreger:
 



  Echte Mehltaupilze (z.B. Erysiphe graminis, Erysiphe cichoracearum, Podosphaera leucotricha, Uncinula necator, Sphaerotheca spp.)
 Rostpilze (z.B. Puccinia tritici, Puccinia recondita, Puccinia hordei, Puccinia coronata, Puccinia striiformis, Puccinia arachidis, Hemileia vastatrix, Uromyces fabae)
 Schorfpilze (z.B. Venturia inaequalis)
 Cercospora spp. (z.B. Cercospora arachidicola, Cercospora beticola)
 Mycosphaereila spp. (z.B. Mycosphaerella fijiensis)
 Alternaria spp. (z.B. Alternaria brassicae, Alternaria mali)
 Septoria spp. (z.B. Septoria nodorum)
 Heminthosporium spp. (z.B. Helminthosporium teres, Heiminthosporium oryzea)
 Plasmopara spp. (z.B. Plasmopara viticola) 
 Pseudoperonospora spp. (z.B. Pseudoperonospora cubensis)
 Phytophthora spp. (z.B. Phytophthora infestans)
 Pseudocercosporella spp. (z.B. Pseudocercosporella herpotrichoides)
 Piricularia spp. (z.B.

   Piricularia oryzae) 



  Ferner wirken die Verbindungen der Formel I beispielsweise gegen Pilze der Gattungen Tilletia, Ustilago, Rhizoctonia, Verticillium, Fusarium, Pythium, Gaeumannomyces, Scierotinia, Monilia, Botrytis, Peronospora, Bremia, Gloeosporium, Cercosporidium, Penicillium, Ceratocystis, Rhynchosporium, Pyrenophora, Diaporthe, Ramularia und Leptosphaeria. Gewisse Vertreter der Verbindungen der Formel I besitzen zudem Wirkung gegen holzschädigende Pilze, wie beispielsweise der Gattungen Coniophora, Gloeophyllum, Poria, Merulius, Trametes, Aureobasidium, Sclerophoma und Trichoderma. 



  Die Verbindungen der Formel 1 zeichnen sich durch prophylaktische und kurative, vor allem aber durch deutliche systemische Wirkung aus. 



  Sie wirken gegen phytopathogene Pilze unter Gewächshausbedingungen bereits bei Konzentrationen von 0,5 mg bis 500 mg Wirkstoff pro Liter Spritzbrühe. Im Freiland werden vorteilhaft Dosierungen von 20 g bis 1 kg Wirkstoff der Formel I pro Hektar und Behandlung zur Anwendung gebracht. Zur Bekämpfung von samen- oder bodenbürtigen Pilzen im Beizverfahren werden mit Vorteil Dosierungen von 0,001 g bis 1,0 g Wirkstoff der Formell pro kg Samen verwendet. 



  Die nachstehenden Beispiele illustrieren die Erfindung. 


 I. Herstellung der Wirkstoffe der Formel I: 
 


 Beispiel 1 
 



  Zu einer Suspension von 0,24 g Natriumhydrid (55-60% in \l) in 20 ml Dimethylformamid tropft man unter Argonbegasung bei 5-10 DEG C 0,637g 2-(2-Brommethyl- phenyl)-acrylsäure-methylester sowie 0,5 g  3-Trifluormethyl-acetophenonoxim in 2 ml Dimethylformamid zu. Man rührt das Reaktionsgemisch weitere 30 Minuten. Nach beendeter Reaktion giesst man das Gemisch auf Wasser und extrahiert das wässrige Gemisch mit drei Portionen Äthylacetat. Die vereinigten organischen Phasen werden zweimal mit Wasser gewaschen, über wasserfreiem Natriumsulfat getrocknet und unter vermindertem Druck eingedampft. Das zurückbleibende \l wird dann an Kieselgel unter Verwendung von n-Hexan/Methylenchlorid (1:1) als Laufmittel chromatographisch gereinigt. 



  Auf diese Weise erhält man den 2-[ alpha - [(E/Z- alpha -methyl-3-trifluormethyl-benzyl)imino]oxyÜ-o-tolyl] -acrylsäure-methylester als farbloses \l. 


 Beispiel 4 
 



  Zu einer Suspension von 0,78 g Natriumhydrid (80% in \l) in 20 ml Dimethylformamid werden unter Argonbegasung bei 0 DEG C 5 g 2-(2-Brommethylphenyl)-glyoxylsäure-methylester-O-methyloxim und 3,2 g  beta -Acetonaphthonoxim in 80 ml Dimethylformamid zugetropft, und das Reaktionsgemisch wird 4 Stunden bei 0 DEG C nachgerührt. Nach beendeter Reaktion wird das Gemisch mit gesättigter Ammoniumchloridlösung hydrolysiert und dreimal mit Diäthyläther extrahiert. Die vereinigten organischen Phasen werden über wasserfreiem Natriumsulfat getrocknet, und das Lösungsmittel wird abdestilliert. Das zurückbleibende \l wird an Kieselgel unter Verwendung von Diäthyläther/n-Hexan (1:1) als Laufmittel chromatographisch gereinigt, und das Produkt aus Methylenchlorid/Diäthyläther/n-Hexan kristallisiert. 



  Auf diese Weise erhält man das 2-[ alpha - [(1-[ beta -Naphthyl]-äthyl)imino]oxyÜ-o-tolyl] -glyoxylsäure-methylester-O-methyloxim als weisse Kristalle, Smp. 97-98 DEG C. 



  In gleicher Weise lassen sich, vorwiegend nach der Methode des Beispiels 4, folgende Methoximinoglyoxylsäure-Derivate gewinnen: 
EMI11.1
 
 
EMI12.1
 
 
EMI13.1
 
 
EMI14.1
 
 



   
EMI15.1
 
 
EMI16.1
 
 
EMI17.1
 
 


 Beispiele 133-141 
 



  Analog dem in Beispiel 1 ("Methode 1") beschriebenen Verfahren erhält man aus dem entsprechenden o-substituierten Benzylbromid der Formel III (U=Br) und dem entsprechenden Oxim der Formel II die in der nachfolgenden Tabelle 3 aufgeführten Verbindungen der Formel I 
EMI17.2
 
 
EMI18.1

Claims (2)

1. Verbindungen der allgemeinen Formel EMI19.1 worin R1 C1-4-Alkyl und U eine Abgangsgruppe bedeuten, mit der Massgabe, dass R1 und C1-2-Alkyl nicht gleichzeitig Methyl bedeuten wenn U für Brom steht.
2. Verbindungen gemäss Anspruch 1, dadurch gekennzeichnet, dass Abgangsgruppe U für Chlor, Brom, Jod, Mesyloxy, Benzolsulfonyloxy oder Tosyloxy steht.
CH01208/91A 1990-06-05 1991-04-23 Zwischenprodukte für Oximäther. CH689421A5 (de)

Priority Applications (47)

Application Number Priority Date Filing Date Title
CH01208/91A CH689421A5 (de) 1991-04-23 1991-04-23 Zwischenprodukte für Oximäther.
PH42549A PH11991042549B1 (de) 1990-06-05 1991-05-30
NZ238346A NZ238346A (en) 1990-06-05 1991-05-31 Aralkyl ethers of oximes and fungicidal compositions thereof
DE59109247T DE59109247D1 (de) 1990-06-05 1991-06-03 Zwischenprodukte für die Herstellung von Oximäthern
PT97848A PT97848B (pt) 1990-06-05 1991-06-03 Processo para a preparacao de compostos aromaticos, por exemplo eteres de oxima
DE59109146T DE59109146D1 (de) 1990-06-05 1991-06-03 Alkylthio-Oximäther-Derivate und deren Verwendung als Fungizide
EP91109035A EP0460575B1 (de) 1990-06-05 1991-06-03 Aromatische Verbindungen
DE59108191T DE59108191D1 (de) 1990-06-05 1991-06-03 Aromatische Verbindungen
AT95112791T ATE182880T1 (de) 1990-06-05 1991-06-03 Alkylthio-oximäther-derivate und deren verwendung als fungizide
CA002043733A CA2043733C (en) 1990-06-05 1991-06-03 Aromatic compounds
EP98115073A EP0893434B1 (de) 1990-06-05 1991-06-03 Zwischenprodukte für die Herstellung von Oximäthern
ES91109035T ES2091834T3 (es) 1990-06-05 1991-06-03 Compuestos aromaticos.
AT91109035T ATE143003T1 (de) 1990-06-05 1991-06-03 Aromatische verbindungen
ES98115073T ES2192722T3 (es) 1990-06-05 1991-06-03 Productos intermedios para la obtencion de oximeteres.
ES95112791T ES2137421T3 (es) 1990-06-05 1991-06-03 Compuestos aromaticos.
DK95112791T DK0694529T3 (da) 1990-06-05 1991-06-03 Alklthio-oximetherderivater samt deres anvendelse som fungicider
DK91109035.5T DK0460575T3 (da) 1990-06-05 1991-06-03 Aromatiske forbindelser
AT98115073T ATE233236T1 (de) 1990-06-05 1991-06-03 Zwischenprodukte für die herstellung von oximäthern
IL9834191A IL98341A (en) 1990-06-05 1991-06-03 Oxides sites, their preparation and use as fungicides
EP95112791A EP0694529B1 (de) 1990-06-05 1991-06-03 Alkylthio-Oximäther-Derivate und deren Verwendung als Fungizide
EP95112790A EP0703215A1 (de) 1990-06-05 1991-06-03 Aromatische Verbindungen
AR91319853A AR247725A1 (es) 1990-06-05 1991-06-03 Compuestos aromaticos procedimiento de preparacion de los mismos, composiciones que los contienen y metodo de aplicacion de los mismos
SG1996001100A SG42939A1 (en) 1990-06-05 1991-06-03 Aromatic compounds
DK98115073T DK0893434T3 (da) 1990-06-05 1991-06-03 Mellemprodukter til fremstilling af oximethere
SU914895703A RU2077527C1 (ru) 1990-06-05 1991-06-04 Оксимэфиры, способ их получения и фунгицидное средство
BR919102305A BR9102305A (pt) 1990-06-05 1991-06-04 Compostos;composicao fungicida,processo para a preparacao de compostos e emprego
CS911688A CZ279709B6 (cs) 1990-06-05 1991-06-04 Aromatické sloučeniny
HU871/91A HU218303B (en) 1990-06-05 1991-06-04 Substituted acrylic acid ester derivatives and fungicidal compositions comprising the same
IE20010092A IE83646B1 (en) 1990-06-05 1991-06-04 Intermediates for the preparation of oxime ethers
IE189991A IE80848B1 (en) 1990-06-05 1991-06-04 Aromatic compounds
SK1688-91A SK278282B6 (en) 1990-06-05 1991-06-04 Benzyloximeter derivatives and their manufacturing method, fungicidal agent containing these compounds as active substances as well as application of these compounds in the agriculture
KR1019910009225A KR0172948B1 (ko) 1990-06-05 1991-06-04 살진균 활성이 있는 방향족 화합물
PL91290533A PL168218B1 (pl) 1990-06-05 1991-06-04 Srodek grzybobójczy PL PL
IE970618A IE83213B1 (en) 1990-06-05 1991-06-04 Alkylthio-oximether Derivatives and their Use as Fungicides
HU0000906A HU0000906D0 (en) 1990-06-05 1991-06-04 Aromatic compounds
AU78167/91A AU633735C (en) 1990-06-05 1991-06-04 Aromatic compounds
JP3160979A JP3000240B2 (ja) 1990-06-05 1991-06-05 芳香族化合物
LVP-93-420A LV10609B (en) 1990-06-05 1993-05-25 Fungicidal oxyme ethers, process for preparing thereof, fungicidal compositions and method for controlling fungi
US08/114,991 US6407100B1 (en) 1990-06-05 1993-09-01 Fungicidal aromatic oximes
MD94-0259A MD1025C2 (ro) 1990-06-05 1994-07-11 Oximeteri, procedeu de obţinere a lor, agent fungicid şi procedeu de inhibare a fungilor fitopatogeni
US08/483,727 US6355634B1 (en) 1990-06-05 1995-06-07 Aromatic compounds
IL11848696A IL118486A0 (en) 1990-06-05 1996-05-30 Oxime ethers their preparation and their use as fungicides
GR960402334T GR3021080T3 (en) 1990-06-05 1996-09-19 Aromatic compounds
HK98104803A HK1005721A1 (en) 1990-06-05 1998-06-03 Aromatic compounds
GR990402732T GR3031643T3 (en) 1990-06-05 1999-10-27 Aromatic compounds
LU90620C LU90620I2 (fr) 1990-06-05 2000-08-05 Trifloxystrobine
NL350004C NL350004I2 (nl) 1990-06-05 2002-07-17 Aromatische verbindingen.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH01208/91A CH689421A5 (de) 1991-04-23 1991-04-23 Zwischenprodukte für Oximäther.

Publications (1)

Publication Number Publication Date
CH689421A5 true CH689421A5 (de) 1999-04-15

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CH01208/91A CH689421A5 (de) 1990-06-05 1991-04-23 Zwischenprodukte für Oximäther.

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Country Link
CH (1) CH689421A5 (de)

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