IL31301A - N-tritylimidazolium salts,their preparation and their use for combating fungi - Google Patents

N-tritylimidazolium salts,their preparation and their use for combating fungi

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Publication number
IL31301A
IL31301A IL6831301A IL3130168A IL31301A IL 31301 A IL31301 A IL 31301A IL 6831301 A IL6831301 A IL 6831301A IL 3130168 A IL3130168 A IL 3130168A IL 31301 A IL31301 A IL 31301A
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Israel
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compound
formula
acid
active
process according
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IL6831301A
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IL31301A0 (en
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Bayer Ag
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Priority claimed from DE19681670977 external-priority patent/DE1670977C3/en
Application filed by Bayer Ag filed Critical Bayer Ag
Publication of IL31301A0 publication Critical patent/IL31301A0/en
Publication of IL31301A publication Critical patent/IL31301A/en

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    • 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
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Description

H-iERiroiMlDAZOLlUM SALTS, THEIR PREPARATION AKD SfiEIR UB FOR GOKBATOTG FMGI FARBEMI'ABfllM BAYER AKOTtf&ESEL'. SC AFT 31301/2 The present invention relates to certain new B-tritySradazolium salts, to a process for their production and to their use as fungicides.
It is already known that certain H-tritylimidazoles exhibit fungicidal properties (compare U.S. Patent Specification 3 321 366).
The invention provides the N-tritylimidazoliura salts of the formula in which R is hydrogen, halogen, nitro, cyano, methyl, alkoxy, alkylthio or lower haloalkyl, and Y is an equivalent of an inorganic or organic acid.
The invention also provides a process for the production of N-tritylimidazolium salts of the formula (l) in w hich a tritylimidazole of the formula in which R has the same meaning as in formula (1), is reacted with an inorganic or an organic acid.
It is very surprising that the H-tritylimidazolium salts of the invention exhibit a considerably greater fungicidal activity than the corresponding tritylimidazole bases.
The reaction according to the invention is illustrated 31301/2 by the following equation:- In the above formulae, R is preferably hydrogen, fluorine, chlorine, bromine, nitro, cyano, methyl, alkoxy, alkylmoroap 0 , with, in each, case, 1 to 3 carbon atoms in the alkyl radical or lower haloalkyl with 1 to 3 carbon atoms and 1 to 5 halogen atoms, which are preferably chlorine or fluorine atoms.
Some of the basic tritylimidazole compounds are known, for example, the unsubstituted tritylimidazole. Others, which are new, are the subject of Israel Patent No. 31302.
• ,· ,, The N-tritylimidazoles of the formula (2) are obtained in particular' favourable manner when the appropriate trityl-halide; is reacted with' imidazole in a polar inert organic solvent, such as acetonitrile , dimethyl formarnide or nitromethane , at a temperature of from 0 to 100°0 in the-; resence of an acid binder, such as t.riethylamlne or pyridine. t Tr'ityl chloride is already, known. Some of the tnono- substituted tritylhalid.es are known. The .new. tritylhalides can be prepared in the same manner a3 the known ones .
The preparation of the monosubstituted trityl chlorides may be carried. out as follows: The Grignard compound of the monosubstituted benzene is prepared. The phenylmagnesium bromide so obtained is then -reacted with benzophenone. The organometallic complex compound obtained is subjected to hydrolysis, the appropriate alcohol being formed (compare J. Org. Chem.2> 392 (194-2)).
The chloride may be easily prepared from the alcohol, when the alcohol is reacted with anhydrous hydrogen chloride or with thionyl chloride. The hydroxyl group is replaced by chlorine (compare J. Org. Chem 2> 392 (1942)).
The acid used as starting material for the process according to the invention is an inorganic monobasic or poly-basie acid, or an organic aliphatic mono- or poly-carboxy-lic acid which may be saturated or unsaturated, or an aromatic mono- or poly-carboxylic acid. These organic acids may be substituted, preferably by hydroxyl groups.
It is preferable to use acids which are not phytotoxic. As ie known, some very specific organic acids have a phytotoxic activity. These include the substituted phenoxyacetic acids, phenoxypropionic acids and phenoxybutyric acids, such as 2,4-dichlorophenoxyacetic acid and 2-methyl-4-chloro-phenoxy propionic acid.
Particularly suitable acids are, for example, those in List (a) below :- Hydrochloric acid, hydrofluoric acid, sulphuric acid, phosphoric acid, acetic acid, lactic acid, malonic acid, succinic acid, maleic acid citric acid, tartaric acid, malic acid, benzoic acid and salicylic acid.
The reaction according to the invention may be carried out in the presence of solvents, which term includes mere diluents.
These include especially the chlorinated hydrocarbons such as chlorobenzene and carbon tetrachloride; ethers, such as diethyl ether, dioxamiahd tetrahydrofuran; nitriles, such use strongly polar solvents which dissolve both reaction components as completely as possible. Aqueous diluents are less suitable since losses may occur because of hydrolytic splitting up of the N-trityl compound.
The reaction temperatures can be varied within a fairly wide range. In general, the reaction is carried out at from -10 to 60°C, preferably from 0 to 50°C.
When carrying out the reaction, about one mde of acid is normally used for each mole of imidazole. The reactants are suitably mixed in a solvent which, after the reaction, is evaporated off wholly or in part. It is often expedient to add ether to promote crystallisation.
The active compounds of the invention exhibit a strong fungitoxic activity. Because of their low toxicity to warmblooded animals they are suitable for the control of undesired fungus growth. Their good compatibility with higher plants permits their use as plant protection agents against fungal plant diseases.
The active compounds are particularly suitable- for the control of phytopathogenic fungi on above-the-soil parts of plants as well as against phytopathogenic fungi which attack the plants from the soil.
The active compounds exhibit a particularly high fungicidal potency against powdery mildew fungi from the family of the Erysiphaceae, for example against the fungi of the genera Erysiphe . Oidium and Podosphaera. The active compounds can, however, also be used with good results for the control of other phytopathogenic fungi, for example fungi which cause diseases in rice and ornamental plants.
The active compounds show a good activity against Piricularia oryzae. Pellicularia sasakii and Cochllobols miyabeanus . .cinerescens, a fungus which attacks carnations from the soil, is also inhibited.
The active compounds are distinguished by a high effectiveness in very low concentrations and by a good compatibility with plants. For this reason, dosages higher than necessary for the fungicidal effect can be accepted readily.
The active compounds according to the present invention can be converted into the usual formulations, such as solutions, emulsions, suspensions, powders, pastes and granulates. These may be produced in known manner, for example by mixing the active compounds with extenders, that is, liquid or solid diluents or carriers, optionally with the use of surface-active agents, that is, emulsifying agents and/or dispersing agents. In the case of the use of water as an extender, organic solvents can, for example, also be used as auxiliary solvents.
As liquid diluents or carriers, there are preferably used aromatic hydrocarbons, such as xylenes or benzene, chlorinated aromatic hydrocarbons, such as chlorobenzenes, paraffins, such as mineral oil fractions, alcohols, such as methanol or butanol, or strongly polar solvents, such as dimethyl formamide or dimethyl sulphoxide , . as well as water.
As solid diluents or carriers, there are preferably used ground natural minerals, such as kaolins, clays, talc or chalk, or ground synthetic minerals, such as highly-dispersed silicic acid or silicates.
Preferred examples of emulsifying agents include non- ionic and anionic emulsifiers, such as polyoxyethylene-fatty acid esters, polyoxyethylene-fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkyl sulphonates and aryl sul- phonates; and preferred examples of dispersing agents include lignin, sulphite waste liquors and methyl cellulose. and organic fungicides and/or insecticides.
The formulations contain, in general, from 0.1 to 95, preferably from 0.5 to 90 per cent by weight of active compound.
The active compounds may be used as such or in the fcrrn of their formulations or of the application forms prepared therefrom, such as ready-to-use solutions, emulsions, suspensions, powders, pastes and granulates. Application may be effected in the usual manner, for example by spraying, squirting, watering or scattering.
The concentrations for actual application may vary within very wide ranges. * Normally, they are from 0.00001 to 2%, preferably from 0.0001 to Vf. If the active compounds are applied acoording to special methods, for example according to the ultra-low-volume method, the concentrates may have concentrations of active compound from 10 to 80$, preferably from 20 to 60 .
The invention provides a fungicidal composition containing as active ingredient a compound of the formula (1) in admixture with a solid diluent or carrier or in admixture with a liquid diluent or carrier containing a surface-active agent .
The invention also provides a method of combating fungi which comprises applying to the fungus or to a fungus habitat a compound of the formula (l) alone or in the form of a composition containing as active ingredient a compound of the formula (l) in admixture with a solid or liquid dilua± or carrier.
The invention also provides crops protected from damage by fungi by being grown in areas in which immediately prior to and/or during the time of growing a compound of the formula (1) was applied alone or in admixture with a solid or illustrated by the following Examples A-G. ' s Example A Podosphaera test (powdery mildew of apples) [Protective i Solvent: 4.7 parts by weight acetone Emulsifier: 0.3 t>art by weight alkylaryl polyglycol ether Water: 95.0 parts by weight The amount of active compound required for the desired concentration of the active compound in the spray liquid is mixed with the stated amount of solvent, and the concentrate is diluted with the stated amount of water which contains the stated additions.
Young apple seedlings in the 4-6 leaf stage are sprayed with the spray liquid until dripping wet. The plants remain in a greenhouse for 24 hours at 20°C and at a relative atmospheric humidity of 70%. They are then inoculated by dusting with conidia of the apple powdeiymildew causative organism (Podosphaera leucotricha Salm. ) and placed in a greenhouse at a temperature of 21-23°C and at a relative atmospheric humidity of about 70%.
Ten days after the inoculation, the infestation of the seedlings is determined as a percentage of the untreated but also inoculated control plants. 0% means no infestation; 100% means that the infestation is exactly as great as in the case of the control plants.
The active compounds, the concentrations of the active compounds and the results can be seen from the following Tables 1 and 2: Table 1 Podo8phaera test (protective) Infestation as a percentage of the infestation of the un¬ Active compound treated control with a concentration of active compound (in ) of 0.0031 0.00156 known: Active compounds according to the invention:-according to formula (1) in which R is H and Y has the following meanin :- Table 1 (Contd) Podosphaera test (protective) Infestation as a percentage Active compound of the infestation of the untreated control with a concentration of active compound (in ) of 0.0031 0.00156 COOH CHOH 50 41 CHOH COO*9 CH^COO Θ (11) 56 55 COOH CHp .CH5 (14) - 53 C 1OO © Example B Example A was repeated using the compounds and obtaining the results given in Table 2.
Table 2 Podosphaera test (Protective) Infestation as a percentage of the infestation of the un¬ Active compound treated control with a coneen tration of active compound (in ) of 0.0031 0.00156 Active compounds according to Formula (l). R and Y having the following meaning: Y R O5 o-P ( 27 ) CH H Θ COO m-F (28) 16 CHOH COO Θ I CHOH P-F (30) 21 18 σοοΘ - 12 - •31301/2 Table 2 (Coritd) Podosphaera teat (Protective Infestation as a percentage- Active compound of the infestation of. the untreated control with a concen-r tration of active compound (in #)of 0.0031 0.00156 R -CI (33) Example C Example Λ Was repeated using the compounds given in Table 3. below,, and the results were compared with those obtained when using the corresponding free bases which are compounds according to Israel Patent 31302.
TABLE 3 Podosphaera test (Protective Active Compound Infestation as a 'percentage of the infestation of the untreated . . ; control with a concentration of active compound (in ) of ' ; 0,00156 0,00178 Compound according to Israel Patent No. 31302 TABLE 3 (cont ... ) Podosphgra test (Protective Active Compound Infestation as a percentage of the infestation of the untreated control with a concentration of active compound (in f>) of 0.00156/° 0.0017876 Compound according to Israel. Patent No. 31302 TABLE 3 (cont...) Podosphaera test (Protective Active Compound Infestation as a percentage of the infestation .of the Untreated control with a concentration of ■Example D Erysiphe test Solvent: 4.7 parte by weight acetone Emulsifier: 0.3 part by weight alkylaryi polyglycol ether Water: parts by weight The amount of the active compound required for the desired concentration in the spray liquid ie mixed with the stated amount of the solvent, and the concentrate is diluted with the stated amount of water containing the stated additions.
Young cucumber plants (Delikatess variety) with about three foliage leaves are sprayed with the spray liquid until dripping wet. The cucumber plants remain in a greenhouse for After 12 days, the infestation of the cucumber plants is' determined as a percentage of the untreated but also inoc ulated control plants. 0$ means no infestation; lOQfi that the infestation is exactly ns great as in the case of the control plants.
The active compounds, the concentrations of the active compounds and the results can be seen from the following Table 3 Erysiphe test Infestation as a percentage of the infestation of the Active compound untreated control with concentration of active compound (in i>) of 0.00019. known: Active compounds according to the invention:-according to Formula (l) in which R is H and Y has the following meaning:- 01 Θ (6) 15 OH 0 OH -CH-COO® ^ 3 Table 7> (Oontd) Brysiphe test Active compound Infestation as a percentage of the infestation of the untreated control with concentration of active compound (in o) i 0.00019 a- o ooi 8 COOH I CHOH 10 I (9) CHOH coo CH-C00H I 2 Λ HO-C-000 Θ (10) 10 I C^-COOH θΗ,σοο Θ (11) 20 COOH I Example # Example jc was repeated using the compounds and obtaining the results given in Table Table & Ery8iphe test Infestation as a percentage of the infestation of the Active compound untreated control with concentration of active compound (in ) of 0.00019 Active . compounds according to Formula (l), R and Y having the following meaning: Y R CHOH o-F (27) σοοθ OH, I 3 m-F (28) CHOH I Θ COO CH I 3 p-F (30) 10 CHOH COO© Θ 01 m-Cl (33) CHOH m-Cl (34) I COO Example ji Mycelium growth test Nutrient medium used: parts by weight agar-agar Proportion of solvent to nutrient medium: 2 parts by weight acetone 100 parts by weight agar nutrient medium.
The amount of active compound required for the desired concentration of active compound in the nutrient medium is mixed with the stated amount of solvent. The concentrate is thoroughly mixed, in the stated proportion with the liquid nutrient medium (which has been cooled to 42°C). and is then poured into Petri dishes of 9 cm diameter. Control dishes to which the preparation has not been added are also set up.
Vfhen the nutrient medium has cooled and solidified, the dishes are inoculated with the species of fungi stated in the Table and incubated at about 21°C.
Evaluation is carried out after 4-10 days, dependent upon the speed of growth of the fungi.. When evaluation is carried out the radial growth of the mycelium on the treated nutrient media is compared with the growth on the control nutrient media. In the evaluation of the fungus growth, the following characteristic values are used:- 0 no fungus growth 1 very strong inhibition of growth 2 medium inhibition of growth 3 slight inhibition of growth 4 growth equal to that of untreated control.
The active compounds, their concentrations and the results obtained can be seen from the following Table 5:- Table J$ 6 Mycelium growth test Concentration of active Piricularia Active compounds compound oryzae known: Active compounds according to the invention:- according to Formula (1)» in which R is H and Y has the following meaning:- Θ CI (6) 10 t-i Table % (Contd) Mycelium growth test Fungi Active compounds Concentration of Piricularia Phia active compound oryzae cine COOH CHOH I CHOH (9) 10 1 Θ COO CH -C00H H0-C-C00 9 (10) 10 CH2-C00H The process of the invention is illustrated by the following Examples 1-4.
Example 1 N-triphenylmethylimidazolium lactate 31 g N-tritylimidazole are dissolved in acetonitrile by heating; lOg (0.11 mole) d, 1-lactic acid are then added.
The residue after the solvent has been distilled off is made to crystallise by covering with a layer of ether; the crystalline product is washed with ether and dried.
Yield: 40 g of colourless crystalline powder of m.p. 170-180°C.
Example 2 N-triphenylmethylimldazolium chloride 31 g N-tritylimidazole are dissolved in 400 ml carbon tetrachloride, and hydrogen chloride is then introduced at room temperature. The hydrochloride precipitated after some time and is filtered off with suction. It is recrystallised from acetone/ether (1:1).
Yield: 33 g of colourless crystals of m.p. 141°C.
Example 3 1-( p-ch orophenylbisphenylmethylimidazolium chloride g l-(p-chlorophenylbisphenylmethyl)-imidazole are dissolved in 250 ml carbon tetrachloride. Hydrogen chloride is introduced at room temperature until about 1.5 equivalents of hydrogen chloride are taken up. The hydrochloride precipitates and, after being left to stand for two hours, is filtered off with suction, washed with carbon tetrachloride and dried.
Yield: 22 g of colourless crystalline powder of m.p. 128-130°C.
In analogous manner, the following substances accordin σοοΗ ΗΟΗ Η 174-180 ΪΗΟΗ (9) σοο Θ CH^COO (11) Η 231 ΟΗ- CH II (13) Η 158-160 CH I Θ CH=CH-COO σοοΗ I I ?Η2 _ (14) Η 188-189 σοο COOH I CH »Η (trans) Η 200-206 000 Θ <8) Example 4 The following compounds were prepared in analogous manner. m.p. 0 01θ o-Ol (26) 159 0¾ CHOH o-P (27) 120 I Θ 000 OH, OHOH P-Cl (32) 90 000 Θ σι ® m-01 (33) 153 to 155 OH, I m-Cl (34) 80 to 90 OHOH 000 Θ Preparation of starting materials, l-(p-chlorophenylbisphenyl methyl)-imidazole:- - - 13.6 g (0.2 mole) imidazole are dissolved in 200 ml of dry acetonitrile, and a solution of 31.4 g (0.1 mole) p-chlorophenylbisphenylmethyl chloride in 50 ml dimethyl form-amide is added. Heating at 80°C is effected for 3 hours, followed by clarification with activated charcoal distillation of the solvent and removal of the imidazole hydrochloride by digestion of the residue with water. After drying, recrystall-isation from light petroleum is effected.
Yield: 31 g of colourless crystalline powder of .p. 139-140°C Preparation of the p-chlorophenylbisphenylmethyl chloride required as starting material :- 205 g bromobenzene and 29 g magnesium are reacted in 1 1 of ether to give phenyl magnesium bromide and to this there are added dropwise 216 g of p-chlorobenzophenone dissolved in 1 1 of benzene, and stirring is effected for 24 hours.
Hydrolysis is then carried out with dilute hydrochloric acid, the solvent layer is taken off, and drying and distillation are then effected. 306 g p-chlorophenylbisphenylcarbinol are obtained. This is taken up in 1 1 of benzene, 50 g calcium chloride are added, and hydrogen chloride is introduced into the solution until saturation. The oily product obtained after removal of the solvent crystallises after some time. By vigorous suction filtration, 220 g p-chlorophenylbisphenylmethyl chloride of m.p, 88°C are obtained. 31301/2

Claims (9)

1. CLAIMS 1. D-trltylimidazoliuH salts of the formula in which R is hydrogeny halogen, nitro, cyano, methyl, alkoxy, or alkylthio of 1 to 3 carbon atoms iri.the alky1 group or lower haloalkyl, and Y is an equivalent of an inorganic or organic acid.
2. Compounds according to Claim 1, imhich R is hydrogen, fluorine, chlorine, bromine, nitro, cyano, methyl, alkoxy or alkylthio with 1 to 3 carbon atoms or lower haloalkyl with 1 to 3 carbon atoms and 1 to 5 ; halogen atoms and Y is the equivalent of a monobasic or pol basic inorganic acid or an aliphatic or polycarboxylic acid which may be unsaturated, or an aromatic mono or polycarboxylic acid, which organic acid equivalent may be substituted by one or more hydroxyl groups. 3· 4. 5· The compound of the formula 6. The compound of the formula. 7. The compound of the formula 8. compound of the formula Th© compotuad. of the formula The compound of the formula Ths compound of the formula Th© compound of th© formula 17. The compound of the formula The compound of the formula 9?.» Sh© compound of the formula The compound of the formula 21. Δ process for th© production of compounds of the formula (l) in which a tritylimidazole of the formula in which R has the same meaning as in claim 1, is reacted with an inorganic or organic acid. 22. A process according to claim 21 in which the reaction is carried out at -10 to 60°C„ 2
3. A process according to Claim 2.2 in which the reaction is carried out at 0 to 50°C. 2
4. A process according to any of Claims 21 to 23 in which the reaction is carried out in the presence of an inert solvent. 2
5. A process according to Claim 24 in which tie solvent is a strongly polar solvent, 2
6. A process according to any of Claims 21 to 25 in which approximately equimolar quantities of the reactants are used. 2
7. A process according to any of Claims 21 to 26 in which the acid is one of those hereinbefore mentioned in ^ist (a). 2
8. A process for the production of compounds of the formula (l) substantially as described herein with reference to the Examples. 2
9. Fungicidal compositions containing as active ingredient a compound according to Claim 1 in admixture with a solid diluent or carrier or in admixture with a liquid diluent or carrier containing a surface->active agent. 30. Compositions according to Claim 29 containing from 0.1 to 5$ by weight of the active compound. 31. A method of combating fungi which comprises applying to the fungus or to a fungus habitat a compound according to Claim 1 alone or in tie form of a composition according to Claims 29 or 30. - 20 - i \ 31301/2 32, A method according to Claim 31 in \hlch a composition is used containing from 0.00001 to 2cfi and preferably from 0.0001 to 1$ by weight of the active compound. 33· A method according to Claim 1 in which tie compound is in a concentration of from 10 to QOe, by weight, and is applied according to the ultra-low-volume method. 34. A method according to any of Claims 31 to 33 in which the compound is one of those mentioned in any of Examples A to E. 35· Crops protected from carnage by fungi by being grown in areas in which immediately prior to and/or during the time of the growing a compound according to Claims 1 was applied alone or in admixture with a solid or liquid diluent or carrier. PC/rb
IL6831301A 1968-01-29 1968-12-20 N-tritylimidazolium salts,their preparation and their use for combating fungi IL31301A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19681670977 DE1670977C3 (en) 1968-01-29 1968-01-29 N-trityl imidazolium salts

Publications (2)

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IL31301A0 IL31301A0 (en) 1969-02-27
IL31301A true IL31301A (en) 1972-07-26

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IL6831301A IL31301A (en) 1968-01-29 1968-12-20 N-tritylimidazolium salts,their preparation and their use for combating fungi

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JP (1) JPS4825188B1 (en)
AT (2) AT300458B (en)
BE (1) BE727489A (en)
BR (1) BR6804399D0 (en)
CH (1) CH511561A (en)
CS (1) CS153028B2 (en)
ES (1) ES362951A1 (en)
FR (1) FR1599525A (en)
GB (2) GB1261880A (en)
IL (1) IL31301A (en)
PL (2) PL82141B1 (en)
SU (1) SU400093A3 (en)

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SU400093A3 (en) 1973-10-03
JPS4825188B1 (en) 1973-07-26
IL31301A0 (en) 1969-02-27
BR6804399D0 (en) 1973-02-22
AT300458B (en) 1972-07-25
FR1599525A (en) 1970-07-15
BE727489A (en) 1969-07-28
CH511561A (en) 1971-08-31
PL82141B1 (en) 1975-10-31
AT283354B (en) 1970-08-10
GB1260211A (en) 1972-01-12
ES362951A1 (en) 1970-11-16
GB1261880A (en) 1972-01-26
CS153028B2 (en) 1974-02-22
PL76031B1 (en) 1975-02-28

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