IE46471B1 - Novel oxime derivatives and their preparation - Google Patents

Novel oxime derivatives and their preparation

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Publication number
IE46471B1
IE46471B1 IE429/78A IE42978A IE46471B1 IE 46471 B1 IE46471 B1 IE 46471B1 IE 429/78 A IE429/78 A IE 429/78A IE 42978 A IE42978 A IE 42978A IE 46471 B1 IE46471 B1 IE 46471B1
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IE
Ireland
Prior art keywords
formula
oxime
compound
atom
group
Prior art date
Application number
IE429/78A
Other versions
IE780429L (en
Original Assignee
Ciba Geigy Ag
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Filing date
Publication date
Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag
Publication of IE780429L publication Critical patent/IE780429L/en
Publication of IE46471B1 publication Critical patent/IE46471B1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
    • 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
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen
    • A01N35/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen containing a carbon-to-nitrogen double bond
    • 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
    • A01N37/34—Nitriles
    • 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
    • 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
    • A01N37/52—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 groups, e.g. carboxylic acid amidines
    • 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
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/04—Sulfonic acids; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/04—Sulfonic acids; Derivatives thereof
    • A01N41/06—Sulfonic acid amides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
    • C07C259/02—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by halogen 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
    • C07D307/02—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
    • C07D307/02—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
    • C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • C07D307/56—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 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Environmental Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Toxicology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Furan Compounds (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Cultivation Of Plants (AREA)

Abstract

Novel compositions which are suitable in agriculture for crop protection contain, together with suitable carrier material, at least one active ingredient from the series comprising oxime ethers, oxime esters or oxime carbamates, the active substance having the formula I in which the substituents are as defined in Claim 1. The compositions can be used advantageously for crop protection. Such compositions have antidote properties for protecting plants against aggressive agrochemicals and, besides, have other plant-regulating and pesticidal properties.

Description

This invention relates to novel oxime derivatives and their preparation.
According to the invention there are provided compounds of the general formula I wherein represents a chlorine atom or a trifluoromethyl or nitro group, R^ represents a hydrogen or chlorine atom or a cyano group, R3 represents a hydrogen atom or a methyl group, R^ represents an amido, methoxycarbonyl, ethoxy-. carbonyl or cyano group, and X represents a hydrogen or chlorine atom or a cyano or a methyl group.
Preferred are those compounds of the formula I wherein R^ represents a methoxycarbonyl group.
The compounds of the formula I have a plant growth regulating action which in the case of high applied amounts of 6 kg per hectare and more can shift the plant growth regulating action in the direction of a herbicidal action.
The compounds of the formula I may be prepared by processes known per se (Organic Reactions 1953, Vol. 7, pages 343 and 373, Journal f. prakt. Chemie 66, page 353; Liebigs Ann 250, 165) namely by etherifying an oxime of the formula II R (wherein R , R2 and X are as defined above) or an oxime 10 salt thereof with a halide of the formula III Hal-CH-R. (Ill) I 4 *3 (wherein R3 and R^ are as defined above and Hal represents a halogen, preferably chlorine or bromine, atom).
The etherification of substituted α-oximino compound 15 is effected advantageously with the compounds in the form of their salts, particularly in the form of their alkali metal salts or ammonium salts as is shown in the following selected example CH„ oximealkaneearboxylic acid esters of the formula I (in the above diagram Hal denotes halogen, especially Cl or Br).
Suitable as solvents for obtaining the compounds of 5 the formula I are essentially all representatives which behave inertly under the conditions of the reaction.
For example, hydrocarbons, particularly however polar solvents, such as acetonitrile, dioxane, Cellosolve or DMF, but also ketones, such as methyl ethyl ketone, acetone, etc. Solvents containing hydroxyl groups are excluded. (Cellosolve is a Registered Trade Mark).
The temperatures are generally in the range of -10°C to about 150°C, preferably between 20° and 120°C.
As agents for splitting off hydrogen halide when a 15 free oxime of formula II is used, it is possible to use bases such as tert, amines (triethylamine, triethylenediamine, piperidine, etc.). Also a suspension of sodium carbonate in the anhydrous reaction medium suffices in some cases. 6 4 71 - 5 Oximes are present in two stereoisomeric forms, the syn-form and anti-form. The compounds of the formula X can be present in either of these forms in the pure state or as mixtures of both. By compounds of the formula I are accordingly meant, within the scope of the present specification, both stereoisomeric forms on their own, or as mixtures with each other in any reciprocal quantitative ratio.
The compounds of the formula I may be prepared by processes analogous to the following although the products of Examples 1 and 2 are not in accordance with the present invention.
Example 1 33.6 g (0.2 mol) of phenylglyoxylonitrile-oxime sodium salt and 25 g (0.22 mol) of chloroacetic acid methyl ester in 200 ml of acetonitrile are held for 3 hours at 60-70°C with thorough stirring, in which time the suspension becomes greatly refined. After a further few hours, filtration is performed; the residue is subsequently washed with acetonitrile, and the combined filtrates are concentrated in vacuo to leave an oily residue, which becomes solid after about 24 hours, m.p. 68-70°C; Recrystallised from isopropanol: m.p. 71-72°C.
. C-C=N N-0-CH2-C00CH Example 2 Production of a-Cyanobenzylidene-amino-oxacetamide 845 g (5 mols) of benz-acetonitrileoxime as Na salt is suspended in 2.5 litres of acetonitrile, and there is slowly added in the presence of catalytic amounts of KI, with stirring, 468 g (5 mols) of chloroacetamide. The reaction mixture is refluxed for 12 hours; it is then cooled and subsequently allowed to flow into about 12 litres of water. While'the salts present are dissolving, the final product precipitates in crystalline form: 882 g (= 86.8% of theory), m.p. 128-129°C (from ethanol).
The following compounds were prepared in this manner. 6 4 7 1 n-o-q Comp. No.RiR2 X Q 1 -Cl -Cl -CN -ch2-co-nh2 2 -Cl -Cl -CN -ch2~cooch3 3 -Cl -Cl -CN -CH(CH3)-COOCH3 4 -Cl -CN -CN -CH2-COOCH3 5 -Cl -CN -CN -CH(CH3)-COOCH3 6 -cf3 -Cl -CN -CH(CH3)-COOCH3 7 -Cl -CN -ch2-cooc2h5 8 -no2 H -CN -CH(CH3)-COOCH3 9 -Cl -Cl -Cl -CH2-CN 10 -Cl -Cl -Cl -CH2-COOCH3 11 -Cl -Cl -Cl -CH(CH3)-COOCH3 12 -Cl -Cl -CH3 -CH2-COOCH3 13 -Cl -Cl -°Η3 -CH(CH )-COOCH 3 3 14 -Cl -Cl H -CH -COOCH3 15 -Cl -Cl H -CH(CH3)-C00CH3 16 -CF3 -Cl H -CH2-COOCH3 17 -CF3 -Cl H -CH(CH3)-COOCH3 6 4 71

Claims (7)

1. CLAIMS : - , (I) wherein R^ represents a chlorine atom or a trifluoromethyl or nitro group, R^ represents a hydrogen or chlorine atom or a cyano group, R 3 represents a hydrogen atom or a methyl group, R^ represents an amido, methoxycarbonyl, ethoxycarbonyl or cyano group, and X represents a hydrogen or chlorine atom or a cyano or a methyl group.
2. A compound according to Claim 1, wherein R 4 represents a methoxycarbonyl group.
3. A compound of the formula
4. A process for I as claimed in Claim 1 an oxime of the formula preparing a compound of which process comprises the formula etherifying II 4 6 4 71 ~ 9 - (wherein R , R 2 and X are as defined in Claim 1) or an oxime salt thereof with a halide of the formula ill Hal-CH-R. (Ill) I 4 R 3 5. (wherein and R^ are as defined in Claim 1 and Hal represents a halogen atom).
5. A process according to Claim 4, wherein an alkali metal or ammonium salt of a compound of the formula II is etherified with the halide of the formula III. 10
6. A process according to Claim 4 or 5, wherein, in the halide of the formula III, Hal represents a chlorine or bromine atom.
7. A compound according to Claim 1 prepared by the process claimed in any one of Claims 4 to 6. F.R. KELLY & CO., AGENTS FOR THE APPLICANTS.
IE429/78A 1977-03-02 1978-03-01 Novel oxime derivatives and their preparation IE46471B1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH260677A CH632130A5 (en) 1977-03-02 1977-03-02 Compositions on the basis of oxime ethers, oxime esters or oxime carbamates which are suitable in agriculture for crop protection

Publications (2)

Publication Number Publication Date
IE780429L IE780429L (en) 1978-09-02
IE46471B1 true IE46471B1 (en) 1983-06-29

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AT (1) AT370585B (en)
AU (1) AU515449B2 (en)
BE (1) BE864436A (en)
BG (1) BG30612A3 (en)
BR (1) BR7801252A (en)
CA (1) CA1149398A (en)
CH (1) CH632130A5 (en)
CS (1) CS223867B2 (en)
DD (2) DD146593A5 (en)
DE (1) DE2808317A1 (en)
DK (1) DK93378A (en)
EG (1) EG13159A (en)
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FI (1) FI780640A (en)
FR (1) FR2387945A1 (en)
GB (1) GB1601752A (en)
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AT370585B (en) 1983-04-11
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AR229079A1 (en) 1983-06-15
DE2808317C2 (en) 1991-05-08
DD146593A5 (en) 1981-02-18
AU515449B2 (en) 1981-04-02
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ATA145278A (en) 1982-09-15
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