IL42401A - Antibiotic substances b-41,their production and their use as insecticides and acaricides - Google Patents
Antibiotic substances b-41,their production and their use as insecticides and acaricidesInfo
- Publication number
- IL42401A IL42401A IL42401A IL4240173A IL42401A IL 42401 A IL42401 A IL 42401A IL 42401 A IL42401 A IL 42401A IL 4240173 A IL4240173 A IL 4240173A IL 42401 A IL42401 A IL 42401A
- Authority
- IL
- Israel
- Prior art keywords
- formula
- hydrogen atom
- methyl group
- group
- bond
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
- C07G11/00—Antibiotics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/01—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing oxygen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Wood Science & Technology (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- Genetics & Genomics (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Compounds Of Unknown Constitution (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Claims (11)
1. A compound having the formula wherein R, represents a hydrogen atom or a methyl group; R2 represents a methyl grou "or when 1 is hydrogen Rg may also represent a pyrroyloxymethyl group of the formula ; R_ represents a methyl group or an ethyl group? R^ and ^ are each a hydrogen atom, or, when Rg anc Rj are. each a methyl group, A may also represent a group of CH3 the formula -0C0CH-(CH2)j-CH-- in which case R^ is a hydroxy group; Rg and R^ together represent a C-0 bond, but when R^ , and R^ are each a. methyl group and R^ and R^.are each hydrogen, then Rg and R^ may also be each a hydrogen atom.
2. The compound of formula I in Claim 1, wherein R1 is a hydrogen atom, is a methyl group, R^ is a methyl group, R^ and R^ are each a hydrogen atom and Rg and R^ together represent a C-0 bond. - 20 » 42401/2
3. The compound of formula I in. Claim 1, wherein is a hydrogen atom, g is a methyl group, R.. is an ethyl group, R^ and Rpj are each a hydrogen atom and Rg and R^ together represent a 0-0 bond .
4. The compound of formula I in Claim 1 , wherein R^ is a methyl group, Rg is a methyl group, ^ is a methyl group, R^ and R,. are each a hydrogen atom and Rg and R^ together represent a C-0 bond.
5. The compound of formula I in Claim 1, wherein is a methyl group, Rg is a methyl group, R^ is an ethyl group, R^ and Rj are each a hydrogen atom and Rg and R^ together represent a C-0 bond.
6. The compound of formula I in Claim 1, wherein 1 is a hydrogen atom, 2 is the pyrroyloxymethyl group, R^ is a methyl group, R^ and Bp. are each a hydrogen atom and Rg and R^ together represent a C-0 bond.
7. The compound of formula I in Claim 1 , wherein R1 is a hydrogen atom, R2 is the pyrroyloxyme hyl group, R^ is an ethyl group, R^ and R-. are each a hydrogen atom and Rg and ^ together represent a C-0 bond.
8. A compound according to Claim 1 having the formula 42401/2 .,,
9. An antibiotic substance B-^l-Ag-. effective against harmful insects, said substance being a colorless amorphous powder form which is difficultly soluble in water and easily soluble in n-hexane, benzene, acetone, ethanol and chloroform and has the formula I in Claim 1 , in which R^ is a hydrogen atom, R5 is a methyl group, R., is a' methyl group, RA is a group of the formula _oco-CH-(C*i ) -CH » R5 iS ^^νοχ^ ' and Rg and R^ together represent a C-0 bond*; said substance . has a molecular -formula of C^gK^gO^ Q, a compositio of 71.75%Tcarbon and 8.26% hydrogen and the following ■ properties; molecular weights of 672.1 obtained by an osmometric method. in acetone and of 672 according 20 1 mass spectrum; a specific rotatory power of (° D ° · ' '\ +5*-° obtained with the concentration of a sample of 5 mg./2 ml. and the length of a layer of 10 cm. in acetone; no p a at a pK ranging from 2 to 12; absorption maximum in the ultraviolet region of the spectrum at 24-5 ιημ; characteristic absorption bands j in the infrared region shown in Fig. 11; nuclear . 1 magnetic resonance spectrum in (CD^^CO shown in I Fig. 20; main peaks of the mass spectrum 672, 181, j 153 and.151 obtained under the conditions of 75 eV j at ionization room temperature of 2o6eC. and a sample temperature of 120-190°C; and the following color reactions according to a thin layer chromatography, ■ yellow to iodine/chloroform, negative to ninhydrin, reddish purple to sulfuric acid and yellow to potassium permanganate.
10. An- antibiotic substance B-41-B^ effective against harmful insects, said substance bein a -29- 42401 / 3 ethanol and chloroform and has the formula I in Claim 1 , i ethyl is substance has a molecular formula of a composition of 68,006 carbon and 8·32# hydrogen and the following properties; a melting point of 176-178°C ; molecular weights of 629o5 obtained by an osmometric method in acetone and of 686 according to mass spectrum; a specific rotatory power of (° D = obtained with the concentration of a sample of 5 mg./2 ml. and. the length of a layer of 10 cm. in acetone; no pKa at a pH ranging from 2 to 12; absorption maximum in the ultraviolet region of the spectrum at 2 5 πιμ; characteristic absorption bands in the infrared region shown in Fig. 14; nuclear magnetic resonance spectrum in (CD^^CO shown in Fig. 23; main peaks of the mass spectrum .686, 414, 195, .167, 151 and 125 obtained under the conditions of 75 eV at ionization room temperature of · 200eC. and a sample temperature of 120-i90°C; and the following color reactions according to a thin layer chromatography", yellow to iodine/chloroform, negative to ninhydrin, reddish purple to sulfuric acid and yellow to potassium permanganate.
11. A process for producing antibiotic substances B-41-Aj, B-41-A2, B-41-Aj, B-41-A^, B-41-B- B-41-B2, B-41-B^, B-41-C^ and B-41-C2 which comprises cultur-ing a B-41-producing strain belongin to the genus Streptomyces-= and then recovering, either singly or ■ in the form of mixtures , said antibiotic .substances from the fermentation broth.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP47057058A JPS4914624A (en) | 1972-06-08 | 1972-06-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL42401A0 IL42401A0 (en) | 1973-07-30 |
| IL42401A true IL42401A (en) | 1976-02-29 |
Family
ID=13044830
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL42401A IL42401A (en) | 1972-06-08 | 1973-05-30 | Antibiotic substances b-41,their production and their use as insecticides and acaricides |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS4914624A (en) |
| BR (1) | BR7304308D0 (en) |
| CH (2) | CH585789A5 (en) |
| DE (1) | DE2329486C2 (en) |
| ES (1) | ES415591A1 (en) |
| FR (1) | FR2187778B1 (en) |
| GB (1) | GB1390336A (en) |
| IL (1) | IL42401A (en) |
| IT (1) | IT986430B (en) |
| SU (2) | SU588926A3 (en) |
| ZA (1) | ZA733857B (en) |
Families Citing this family (77)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5858164B2 (en) * | 1975-09-06 | 1983-12-23 | イシカワジマハリマジユウコウギヨウ カブシキガイシヤ | Chisel Souchi |
| SE434277B (en) * | 1976-04-19 | 1984-07-16 | Merck & Co Inc | SET TO MAKE NEW ANTIHELMINTICALLY EFFECTIVE ASSOCIATIONS BY CULTIVATING STREPTOMYCS AVERMITILIS |
| US4093629A (en) * | 1977-04-11 | 1978-06-06 | Merck & Co., Inc. | Derivatives of antibiotic substance milbemycin and processes therefor |
| NZ186851A (en) * | 1977-04-11 | 1984-12-14 | Merck & Co Inc | Glycosyloxy derivatives of milbemycin and parasiticidal compositions |
| NZ188459A (en) * | 1977-10-03 | 1982-09-07 | Merck & Co Inc | Derivatives of c-076 compounds and pesticidal compositions |
| PH15982A (en) * | 1977-10-03 | 1983-05-18 | Merck & Co Inc | Selective hydrogenation producta of c-076 compounds and derivatives thereof |
| PH16612A (en) * | 1977-12-19 | 1983-11-28 | Merck & Co Inc | 13-halo and 13-deoxy derivatives of c-076 compounds |
| JPS5632481A (en) * | 1979-08-23 | 1981-04-01 | Sankyo Co Ltd | Antibiotic b-41d, its preparation, and acaricide and anthelminthic agent and repellent containing the same as active constituent |
| JPS57139012A (en) * | 1981-02-23 | 1982-08-27 | Sankyo Co Ltd | Anthelmintic composition |
| DE3372693D1 (en) * | 1982-07-22 | 1987-09-03 | Ici Plc | Methods and compositions of combating pests |
| JPS60141293A (en) * | 1983-12-28 | 1985-07-26 | Kitasato Inst:The | Novel carcinostatic antibiotic substance 81-484 and its production |
| US5169956A (en) * | 1984-06-05 | 1992-12-08 | American Cyanamid Company | Macrolide antibiotic compounds |
| AT396250B (en) * | 1984-09-14 | 1993-07-26 | American Cyanamid Co | METHOD FOR PRODUCING NEW ANTIBIOTICALLY ACTIVE CONNECTIONS |
| GB8606120D0 (en) * | 1986-03-12 | 1986-04-16 | Glaxo Group Ltd | Process |
| EP0254583B1 (en) * | 1986-07-24 | 1994-09-07 | Beecham Group Plc | Parasiticidal milbemycin derivatives, a process for their production, and compositions containing the same |
| US4831016A (en) * | 1986-10-31 | 1989-05-16 | Merck & Co., Inc. | Reduced avermectin derivatives |
| EP0319142B1 (en) * | 1987-11-03 | 1994-04-06 | Beecham Group Plc | Intermediates for the preparation of anthelmintic macrolide antibiotics |
| GB8804440D0 (en) * | 1988-02-25 | 1988-03-23 | Pfizer Ltd | Antiparasitic agents |
| GB8815967D0 (en) * | 1988-07-05 | 1988-08-10 | Pfizer Ltd | Antiparasitic agents |
| GB8917064D0 (en) * | 1989-07-26 | 1989-09-13 | Pfizer Ltd | Antiparasitic agent |
| US5290804A (en) * | 1991-05-01 | 1994-03-01 | Merck & Co., Inc. | Anthelmintic milbemycin analogs of novel microorganisms |
| GB9205007D0 (en) * | 1992-03-07 | 1992-04-22 | Pfizer Ltd | Antiparasitic agents |
| JP2952265B2 (en) * | 1993-11-29 | 1999-09-20 | 井筒屋化学産業株式会社 | Composition and method for preventing pine wilt |
| DE19613972A1 (en) * | 1996-04-09 | 1997-10-16 | Bayer Ag | Injection formulations of avermectins and milbemycins based on castor oil |
| ES2359973T3 (en) | 1998-03-19 | 2011-05-30 | MERCK SHARP & DOHME CORP. | LIQUID POLYMER COMPOSITIONS FOR THE CONTROLLED RELEASE OF BIOACTIVE SUBSTANCES. |
| GB9825402D0 (en) | 1998-11-19 | 1999-01-13 | Pfizer Ltd | Antiparasitic formulations |
| NZ531787A (en) | 2001-09-17 | 2006-12-22 | Lilly Co Eli | Pesticidal formulations for controlling pests in domestic animals |
| US7671034B2 (en) | 2003-12-19 | 2010-03-02 | Merial Limited | Stabilized formulation of ivermectin feed premix with an extended shelf life |
| DE102004053964A1 (en) | 2004-11-09 | 2006-05-11 | Bayer Healthcare Ag | Remedy for demodicosis |
| US8362086B2 (en) | 2005-08-19 | 2013-01-29 | Merial Limited | Long acting injectable formulations |
| BRPI0714194A2 (en) | 2006-07-05 | 2012-12-25 | Aventis Agriculture | 1-aryl-5-alkylpyrazole derivatives, processes for making them and methods for their use |
| SI2639228T1 (en) | 2007-05-15 | 2017-03-31 | Merial, Inc. | Aryloazol-2-yl cyanoethylamino compounds, method of making and method of using thereof |
| EP3050874B1 (en) | 2008-11-14 | 2019-01-09 | Merial Inc. | Enantiomerially enriched aryloazol-2-yl cyanoethylamino paraciticidal compounds |
| NZ592865A (en) | 2008-11-19 | 2013-08-30 | Merial Ltd | Compositions comprising an aryl pyrazole and/or a formamidine, methods and uses thereof |
| EP2327410A1 (en) * | 2009-10-28 | 2011-06-01 | Consiglio Nazionale Delle Ricerche - Infm Istituto Nazionale Per La Fisica Della Materia | Avermectins and milbemycins for the treatment of flavivirus infections |
| NZ600252A (en) | 2009-12-04 | 2014-03-28 | Merial Ltd | Pesticidal bis-organosulfur compounds |
| ES2727588T3 (en) | 2009-12-17 | 2019-10-17 | Merial Inc | Antiparasitic dihydroazole compositions |
| UA108641C2 (en) | 2010-04-02 | 2015-05-25 | PARASITICID COMPOSITION CONTAINING FOUR ACTIVE AGENTS AND METHOD OF APPLICATION | |
| EP2640728B1 (en) | 2010-11-16 | 2016-09-07 | Merial, Inc. | Novel monensin derivatives for the treatment and prevention of protozoal infections |
| US20120329832A1 (en) | 2011-06-27 | 2012-12-27 | Jean Delaveau | Novel Insect-Repellent Coumarin Derivatives, Syntheses, and Methods of Use |
| AU2012275435B2 (en) | 2011-06-27 | 2016-07-21 | Boehringer Ingelheim Animal Health USA Inc. | Amido-pyridyl ether compounds and compositions and their use against parasites |
| LT3172964T (en) | 2011-09-12 | 2020-12-10 | Boehringer Ingelheim Animal Health USA Inc. | Parasiticidal compositions comprising an isoxazoline active agent, method and uses thereof |
| WO2013044118A2 (en) | 2011-09-23 | 2013-03-28 | Merial Limited | Indirect modeling of new repellent molecules active against insects, acarids, and other arthropods |
| US9173404B2 (en) | 2011-11-17 | 2015-11-03 | Merial, Inc. | Compositions comprising an aryl pyrazole and a substituted imidazole, methods and uses thereof |
| HU231098B1 (en) | 2012-02-06 | 2020-08-28 | Boehringer Ingelheim Animal Health USA Inc. | Parasiticidal oral veterinary compositions comprising systemically-acting active agents, methods and uses thereof |
| JO3626B1 (en) | 2012-02-23 | 2020-08-27 | Merial Inc | Topical formulations containing fipronil and permethrin and how to use them |
| CA3059936A1 (en) | 2012-04-20 | 2013-10-24 | Boehringer Ingelheim Animal Health USA Inc. | Parasiticidal compositions comprising benzimidazole derivatives, methods and uses thereof |
| HUE039915T2 (en) | 2012-11-20 | 2019-02-28 | Merial Inc | Anthelmintic compounds and compositions and method of their application |
| RS57469B1 (en) | 2013-01-31 | 2018-09-28 | Merial Inc | Method for treating and curing leishmaniosis using fexinindazole |
| AU2014342241B2 (en) | 2013-11-01 | 2017-09-14 | Boehringer Ingelheim Animal Health USA Inc. | Antiparasitic and pesticidal isoxazoline compounds |
| EP2886640A1 (en) | 2013-12-18 | 2015-06-24 | Riga Technical University | Process for isolation of milbemycins A3 and A4 |
| JP6682719B2 (en) | 2014-04-17 | 2020-04-15 | ベーリンガー インゲルハイム アニマル ヘルス ユーエスエイ インコーポレイテッド | Use of malononitrile compounds to protect animals from parasites |
| JP6616786B2 (en) | 2014-05-19 | 2019-12-04 | メリアル インコーポレイテッド | Anthelmintic compound |
| ES2895826T3 (en) | 2014-06-19 | 2022-02-22 | Boehringer Ingelheim Animal Health Usa Inc | Parasiticide compositions comprising indole derivatives, methods and uses thereof |
| ES2887302T3 (en) | 2014-10-31 | 2021-12-22 | Boehringer Ingelheim Animal Health Usa Inc | Parasiticidal compositions comprising fipronil |
| UY36570A (en) | 2015-02-26 | 2016-10-31 | Merial Inc | INJECTABLE FORMULATIONS OF PROLONGED ACTION THAT INCLUDE AN ISOXAZOLINE ACTIVE AGENT, METHODS AND USES OF THE SAME |
| EP3280413A1 (en) | 2015-04-08 | 2018-02-14 | Merial, Inc. | Extended release injectable formulations comprising an isoxazoline active agent, methods and uses thereof |
| RS62130B1 (en) | 2015-05-20 | 2021-08-31 | Boehringer Ingelheim Animal Health Usa Inc | Anthelmintic depsipeptide compounds |
| AU2016267047A1 (en) | 2015-05-27 | 2017-12-21 | Merial, Inc. | Compositions containing antimicrobial IgY antibodies, for treatment and prevention of disorders and diseases caused by oral health compromising (OHC) microorganisms |
| UY37137A (en) | 2016-02-24 | 2017-09-29 | Merial Inc | ANTIPARASITARY COMPOUNDS OF ISOXAZOLINE, INJECTABLE FORMULATIONS OF PROLONGED ACTION THAT INCLUDE THEM, METHODS AND USES OF THE SAME |
| WO2018039508A1 (en) | 2016-08-25 | 2018-03-01 | Merial, Inc. | Method for reducing unwanted effects in parasiticidal treatments |
| CA3040278A1 (en) | 2016-10-14 | 2018-04-19 | Boehringer Ingelheim Animal Health USA Inc. | Pesticidal and parasiticidal vinyl isoxazoline compounds |
| US11382949B2 (en) | 2016-11-16 | 2022-07-12 | Boehringer Ingelheim Animal Health USA Inc. | Anthelmintic depsipeptide compounds |
| UY37780A (en) | 2017-06-26 | 2019-01-31 | Merial Inc | COMPOSITIONS OF PARASITICIATED GRANULES WITH DOUBLE ACTIVE PRINCIPLE, ITS METHODS AND USES |
| EP3668866B1 (en) | 2017-08-14 | 2023-01-18 | Boehringer Ingelheim Animal Health USA Inc. | Pesticidal and parasiticidal pyrazole-isoxazoline compounds |
| WO2019152808A1 (en) | 2018-02-01 | 2019-08-08 | Yale University | Compositions and methods for inhibition of nuclear-penetrating antibodies |
| WO2019157241A1 (en) | 2018-02-08 | 2019-08-15 | Boehringer Ingelheim Animal Health USA Inc. | Parasiticidal compositions comprising eprinomectin and praziquantel, methods and uses thereof |
| CN112996788B (en) | 2018-07-09 | 2024-07-16 | 勃林格殷格翰动物保健美国公司 | Heterocyclic compounds that anthelmintic |
| WO2020112374A1 (en) | 2018-11-20 | 2020-06-04 | Boehringer Ingelheim Animal Health USA Inc. | Indazolylcyanoethylamino compound, compositions of same, method of making, and methods of using thereof |
| WO2020150032A1 (en) | 2019-01-16 | 2020-07-23 | Boehringer Ingelheim Animal Health USA Inc. | Topical compositions comprising a neonicotinoid and a macrocyclic lactone, methods and uses thereof |
| EP3930684A1 (en) | 2019-03-01 | 2022-01-05 | Boehringer Ingelheim Animal Health USA Inc. | Injectable clorsulon compositions, methods and uses thereof |
| AR118435A1 (en) | 2019-03-19 | 2021-10-06 | Boehringer Ingelheim Animal Health Usa Inc | AZA-BENZOTHIOPHENE AND AZA-BENZOFURAN COMPOUNDS AS ANTIHELMINTICS |
| US20220323421A1 (en) | 2019-07-22 | 2022-10-13 | Intervet Inc. | Soft Chewable Veterinary Dosage Form |
| PH12022553222A1 (en) | 2020-05-29 | 2024-02-12 | Boehringer Ingelheim Animal Health Usa Inc | Anthelmintic heterocyclic compounds |
| EP4262789A1 (en) | 2020-12-21 | 2023-10-25 | Boehringer Ingelheim Vetmedica GmbH | Parasiticidal collar comprising isoxazoline compounds |
| BR112023023856A2 (en) | 2021-05-14 | 2024-01-30 | Syngenta Crop Protection Ag | CONTROL OF INSECT PESTS, MITE AND NEMATODES |
| WO2023203038A1 (en) | 2022-04-19 | 2023-10-26 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
-
1972
- 1972-06-08 JP JP47057058A patent/JPS4914624A/ja active Pending
-
1973
- 1973-05-30 IL IL42401A patent/IL42401A/en unknown
- 1973-06-06 IT IT68686/73A patent/IT986430B/en active
- 1973-06-06 ES ES415591A patent/ES415591A1/en not_active Expired
- 1973-06-07 FR FR7320831A patent/FR2187778B1/fr not_active Expired
- 1973-06-07 CH CH826473A patent/CH585789A5/xx not_active IP Right Cessation
- 1973-06-07 CH CH930276A patent/CH585514A5/xx not_active IP Right Cessation
- 1973-06-07 ZA ZA00733857A patent/ZA733857B/en unknown
- 1973-06-08 GB GB2743773A patent/GB1390336A/en not_active Expired
- 1973-06-08 BR BR4308/73A patent/BR7304308D0/en not_active IP Right Cessation
- 1973-06-08 SU SU731931001A patent/SU588926A3/en active
- 1973-06-08 DE DE2329486A patent/DE2329486C2/en not_active Expired
-
1975
- 1975-08-20 SU SU752167200A patent/SU1360574A3/en active
Also Published As
| Publication number | Publication date |
|---|---|
| AU5663173A (en) | 1974-12-12 |
| ES415591A1 (en) | 1976-07-01 |
| FR2187778B1 (en) | 1976-06-11 |
| ZA733857B (en) | 1975-04-30 |
| GB1390336A (en) | 1975-04-09 |
| CH585789A5 (en) | 1977-03-15 |
| DE2329486A1 (en) | 1973-12-20 |
| SU1360574A3 (en) | 1987-12-15 |
| CH585514A5 (en) | 1977-03-15 |
| IT986430B (en) | 1975-01-30 |
| DE2329486C2 (en) | 1984-01-12 |
| SU588926A3 (en) | 1978-01-15 |
| FR2187778A1 (en) | 1974-01-18 |
| IL42401A0 (en) | 1973-07-30 |
| JPS4914624A (en) | 1974-02-08 |
| BR7304308D0 (en) | 1974-08-29 |
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