IE41140B1 - Fungicidal n-substituted furoic amide derivatives - Google Patents
Fungicidal n-substituted furoic amide derivativesInfo
- Publication number
- IE41140B1 IE41140B1 IE708/75A IE70875A IE41140B1 IE 41140 B1 IE41140 B1 IE 41140B1 IE 708/75 A IE708/75 A IE 708/75A IE 70875 A IE70875 A IE 70875A IE 41140 B1 IE41140 B1 IE 41140B1
- Authority
- IE
- Ireland
- Prior art keywords
- formula
- acid
- prepared
- compound
- reacting
- Prior art date
Links
Classifications
-
- 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
- C07D213/60—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 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/30—Halogen atoms or nitro 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
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no 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
- C07D307/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/06—Six-membered rings
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pyridine Compounds (AREA)
- Pyrane Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
1448810 Furan derivatives CIBA-GEIGY AG 1 April 1975 [2 April 1974 10 Feb 1975] 13332/75 Heading C2C The invention comprises compounds of the Formula (I) in which R is H or methyl. They may be prepared by (a) acylating a compound of Formula (II) with furan (2)-carboxylic acid or an acid halide, anhydride or ester thereof, or (b) reacting a compound of Formula (III) with either an α-halopropionic acid methyl ester in the presence of an alkali metal carbonate, or with butyl lithium or sodium hydride to give the corresponding alkali metal salt, followed by reaction with an α-halopropionic acid methyl ester. The enantiomeric D-form of the compound of Formula (I) may be prepared by reacting the racemic compound of Formula (IV) in known manner with a nitrogen-containing optically active base to give the corresponding salt followed by fractional crystallization and liberation of the acid of Formula IV which is enriched with the optical D-antipode. The D- form of the ester of Formula (II) may then be prepared in conventional manner from the D form of the acid of Formula (IV), followed by acylation as in step (a) above, to give the D- form of the compound of Formula (I). The D- form of the acid of Formula (IV) may also be prepared by replacing the hydroxy group in L(+) lactic acid by halogen and reacting this product with 2,6-dimethylaniline or 2,3,6-trimethylaniline with reversal of the configuration. The compounds of Formula (II) may be prepared by reacting 2,6-dimethylaniline or 2,3,6- trimethylaniline with 2-bromopropionic acid methyl ester. The compounds of Formula (I) are used in fungicidal compositions.
[GB1448810A]
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH457274A CH590608A5 (en) | 1974-04-02 | 1974-04-02 | N-Furoyl-N-aryl-alanine esters - prepd. e.g. by reacting N-aryl-alanine esters with 2-furoic acid or its derivs. |
CH159175A CH603041A5 (en) | 1974-04-02 | 1975-02-10 | N-Furoyl-N-aryl-alanine esters |
Publications (2)
Publication Number | Publication Date |
---|---|
IE41140L IE41140L (en) | 1975-10-02 |
IE41140B1 true IE41140B1 (en) | 1979-10-24 |
Family
ID=25688094
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IE709/75A IE41777B1 (en) | 1974-04-02 | 1975-04-02 | Fungicidal agents |
IE708/75A IE41140B1 (en) | 1974-04-02 | 1975-04-02 | Fungicidal n-substituted furoic amide derivatives |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IE709/75A IE41777B1 (en) | 1974-04-02 | 1975-04-02 | Fungicidal agents |
Country Status (31)
Country | Link |
---|---|
JP (3) | JPS6042202B2 (en) |
AR (2) | AR205189A1 (en) |
AT (2) | AT343407B (en) |
AU (1) | AU465906B2 (en) |
BG (2) | BG26356A3 (en) |
CA (2) | CA1050546A (en) |
CH (1) | CH603041A5 (en) |
CS (2) | CS183789B2 (en) |
DD (3) | DD124733A5 (en) |
DE (2) | DE2560591C2 (en) |
DK (2) | DK141168B (en) |
EG (2) | EG12263A (en) |
ES (2) | ES436174A1 (en) |
FI (2) | FI750921A (en) |
FR (2) | FR2265747B1 (en) |
GB (2) | GB1498199A (en) |
HU (2) | HU172935B (en) |
IE (2) | IE41777B1 (en) |
IL (2) | IL46988A (en) |
IT (2) | IT1049394B (en) |
LU (2) | LU72174A1 (en) |
NL (2) | NL7503755A (en) |
NO (2) | NO141340C (en) |
OA (2) | OA04916A (en) |
PH (2) | PH11792A (en) |
PL (2) | PL98627B1 (en) |
RO (3) | RO73181A (en) |
SE (2) | SE419218B (en) |
SU (4) | SU743561A3 (en) |
TR (2) | TR18508A (en) |
YU (2) | YU39026B (en) |
Families Citing this family (37)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5845433B2 (en) * | 1975-02-10 | 1983-10-08 | チバ・ガイギ− アクチエンゲゼルシヤフト | 2↓-Production method of furancarboxylic acid anilides |
US4147792A (en) * | 1977-02-04 | 1979-04-03 | Ciba-Geigy Corporation | Fungicidal compositions |
CH629939A5 (en) * | 1977-03-29 | 1982-05-28 | Ciba Geigy Ag | MICROBICIDAL AGENT. |
DE2724785A1 (en) * | 1977-05-27 | 1978-12-14 | Schering Ag | FURANCARBONIC ANILIDES, FUNGICIDALS CONTAINING THESE COMPOUNDS AND THE PROCESS FOR THEIR PREPARATION |
BG28977A3 (en) | 1978-02-02 | 1980-08-15 | Montedison Spa | Fungicide means and method for fungus fighting |
CH637368A5 (en) * | 1978-10-27 | 1983-07-29 | Ciba Geigy Ag | ANILINE DERIVATIVES AND Pesticides Manufactured From Them. |
EP0010673B1 (en) * | 1978-10-31 | 1982-01-27 | Bayer Ag | Substituted n-propargyl anilines, process for their preparation and their use as fungicides |
CH641760A5 (en) * | 1978-11-27 | 1984-03-15 | Ciba Geigy Ag | PEST CONTROL. |
CH639940A5 (en) * | 1978-12-05 | 1983-12-15 | Ciba Geigy Ag | Substituted N-alkoxycarbonylethyl-N-acylanilines, microbicides containing them, and process for the preparation of the compounds |
DE2948734A1 (en) * | 1978-12-07 | 1980-06-19 | Ciba Geigy Ag | PEST CONTROL |
DE2940189A1 (en) * | 1979-10-04 | 1981-04-16 | Basf Ag, 6700 Ludwigshafen | ISOXAZOLYLCARBONIC ACID ANILIDE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS FUNGICIDES |
MA19111A1 (en) * | 1979-10-26 | 1981-12-31 | Ciba Geigy Ag | HOMOSERIN DERIVATIVES, PROCESS FOR THEIR PREPARATION AND THEIR USE AS MICROBICIDES |
DE3013908A1 (en) * | 1980-04-11 | 1981-10-22 | Basf Ag, 6700 Ludwigshafen | 2- (N-ARYL-, N-ISOXAZOLYLCARBONYL) -AMINOBUTYROLACTONE, METHOD FOR THE PRODUCTION THEREOF AND FUNGICIDES CONTAINING THEM |
MA19215A1 (en) * | 1980-07-25 | 1982-04-01 | Ciba Geigy Ag | NOVEL ARYLAMINE DERIVATIVES, PROCESS FOR THEIR MANUFACTURE AND USE AS MICROBICIDES. |
DE3030736A1 (en) | 1980-08-14 | 1982-03-25 | Basf Ag, 6700 Ludwigshafen | N-DISUBSTITUTED ANILINE DERIVATIVES, THEIR PRODUCTION, THEIR USE AS MICROBICIDES AND AGENTS THEREFOR |
EP0061836B1 (en) * | 1981-03-19 | 1986-12-30 | Imperial Chemical Industries Plc | Amide derivatives, processes for preparing them, their use as fungicides and pesticidal compositions containing them |
DE3133418A1 (en) * | 1981-08-24 | 1983-03-10 | Basf Ag, 6700 Ludwigshafen | THIAZOLYL AND ISOTHIAZOLYLCARBONIC ACID ANILIDES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS FUNGICIDES |
JPH0326906U (en) * | 1989-07-26 | 1991-03-19 | ||
DE4011172A1 (en) * | 1990-04-06 | 1991-10-10 | Degussa | COMPOUNDS FOR CONTROLLING PLANT DISEASES |
DE4304172A1 (en) | 1993-02-12 | 1994-08-25 | Bayer Ag | Fungicidal active ingredient combinations |
US5723491A (en) * | 1994-07-11 | 1998-03-03 | Novartis Corporation | Fungicidal composition and method of controlling fungus infestation |
DE4429014A1 (en) | 1994-08-16 | 1996-02-22 | Basf Ag | Process for the preparation of cyclic amines |
AR011515A1 (en) * | 1996-12-25 | 2000-08-30 | Agrogene Ltd | DERIVED FROM AMINOBUTIRIC ACID FOR THE PROTECTION OF PLANTS FROM FUNGAL DISEASES AND A METHOD TO PROTECT A CROP AGAINST FUNGAL DISEASES, FOR EXAMPLE, TOMATOES AND POTATOES AGAINST LATE, EARLY MILK, VINEYARD ELVIO, AND |
DE10347090A1 (en) | 2003-10-10 | 2005-05-04 | Bayer Cropscience Ag | Synergistic fungicidal drug combinations |
DE10349501A1 (en) | 2003-10-23 | 2005-05-25 | Bayer Cropscience Ag | Synergistic fungicidal drug combinations |
DE102004049761A1 (en) | 2004-10-12 | 2006-04-13 | Bayer Cropscience Ag | Fungicidal drug combinations |
DE102005026482A1 (en) | 2005-06-09 | 2006-12-14 | Bayer Cropscience Ag | Active substance combination, useful e.g. for combating unwanted phytopathogenic fungus, comprises herbicides e.g. glyphosate and active substances e.g. strobilurin, triazoles, valinamide and carboxamide |
CA2916460C (en) | 2005-06-09 | 2017-10-03 | Klaus Stenzel | Combinations comprising prothioconazole and gulfosinate |
DE102006023263A1 (en) | 2006-05-18 | 2007-11-22 | Bayer Cropscience Ag | Synergistic drug combinations |
JP2010503642A (en) | 2006-09-18 | 2010-02-04 | ビーエーエスエフ ソシエタス・ヨーロピア | Ternary pesticide mixture |
CN101605461A (en) | 2007-02-06 | 2009-12-16 | 巴斯夫欧洲公司 | Pesticide combination |
EP2000028A1 (en) | 2007-06-06 | 2008-12-10 | Bayer CropScience Aktiengesellschaft | Fungicidal active agent compounds |
EP2000030A1 (en) | 2007-06-06 | 2008-12-10 | Bayer CropScience AG | Fungicidal active agent compounds |
DE102007045920B4 (en) | 2007-09-26 | 2018-07-05 | Bayer Intellectual Property Gmbh | Synergistic drug combinations |
IN2012DN01345A (en) | 2009-07-16 | 2015-06-05 | Bayer Cropscience Ag | |
EP2910126A1 (en) | 2015-05-05 | 2015-08-26 | Bayer CropScience AG | Active compound combinations having insecticidal properties |
CN115557887A (en) * | 2022-11-10 | 2023-01-03 | 南京林业大学 | Synthesis of trifluoromethyl pyridine derivative based on Ugi reaction and biological activity research of trifluoromethyl pyridine derivative |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3959481A (en) * | 1969-02-13 | 1976-05-25 | Uniroyal | Method of protecting plants from fungal diseases using furan-3-carboxamide derivatives |
JPS5345364A (en) * | 1976-10-06 | 1978-04-24 | Daiahoiru Kk | Device for controlling extrusion molding die bolt |
-
1975
- 1975-01-01 AR AR258203A patent/AR205189A1/en active
- 1975-02-10 CH CH159175A patent/CH603041A5/en not_active IP Right Cessation
- 1975-03-26 FR FR7509484A patent/FR2265747B1/fr not_active Expired
- 1975-03-26 SE SE7503517A patent/SE419218B/en not_active IP Right Cessation
- 1975-03-26 DK DK135875AA patent/DK141168B/en not_active IP Right Cessation
- 1975-03-26 FI FI750921A patent/FI750921A/fi not_active Application Discontinuation
- 1975-03-26 NO NO751084A patent/NO141340C/en unknown
- 1975-03-26 FR FR7509485A patent/FR2265748B1/fr not_active Expired
- 1975-03-26 NO NO751086A patent/NO142714C/en unknown
- 1975-03-26 SE SE7503518A patent/SE418086B/en not_active IP Right Cessation
- 1975-03-26 FI FI750920A patent/FI63567C/en not_active IP Right Cessation
- 1975-03-26 DK DK135975AA patent/DK141995B/en not_active IP Right Cessation
- 1975-03-27 CA CA223,227A patent/CA1050546A/en not_active Expired
- 1975-03-27 CA CA223,222A patent/CA1050558A/en not_active Expired
- 1975-03-27 AU AU79640/75A patent/AU465906B2/en not_active Expired
- 1975-03-27 NL NL7503755A patent/NL7503755A/en not_active Application Discontinuation
- 1975-03-27 DE DE2560591A patent/DE2560591C2/de not_active Expired
- 1975-03-27 DE DE19752513732 patent/DE2513732A1/en active Granted
- 1975-03-27 NL NL7503754.A patent/NL160821C/en not_active IP Right Cessation
- 1975-03-28 IT IT21867/75A patent/IT1049394B/en active
- 1975-03-28 IT IT21855/75A patent/IT1048806B/en active
- 1975-03-31 OA OA55458A patent/OA04916A/en unknown
- 1975-03-31 OA OA55460A patent/OA04918A/en unknown
- 1975-03-31 PH PH16995A patent/PH11792A/en unknown
- 1975-03-31 PH PH16998A patent/PH13072A/en unknown
- 1975-04-01 RO RO7581867A patent/RO73181A/en unknown
- 1975-04-01 DD DD192060A patent/DD124733A5/xx unknown
- 1975-04-01 LU LU72174A patent/LU72174A1/xx unknown
- 1975-04-01 AT AT244875A patent/AT343407B/en not_active IP Right Cessation
- 1975-04-01 HU HU75CI00001563A patent/HU172935B/en not_active IP Right Cessation
- 1975-04-01 AR AR258204A patent/AR224602A1/en active
- 1975-04-01 YU YU00828/75A patent/YU39026B/en unknown
- 1975-04-01 IL IL46988A patent/IL46988A/en unknown
- 1975-04-01 DD DD185144A patent/DD118510A5/xx unknown
- 1975-04-01 IL IL46989A patent/IL46989A/en unknown
- 1975-04-01 AT AT244675A patent/AT345614B/en not_active IP Right Cessation
- 1975-04-01 HU HU75CI1564A patent/HU173317B/en unknown
- 1975-04-01 DD DD185147A patent/DD118785A5/xx unknown
- 1975-04-01 GB GB13349/75A patent/GB1498199A/en not_active Expired
- 1975-04-01 BG BG7529508A patent/BG26356A3/xx unknown
- 1975-04-01 BG BG7500029507A patent/BG24651A3/en unknown
- 1975-04-01 GB GB1333275A patent/GB1448810A/en not_active Expired
- 1975-04-01 ES ES436174A patent/ES436174A1/en not_active Expired
- 1975-04-01 LU LU72175A patent/LU72175A1/xx unknown
- 1975-04-01 YU YU827/75A patent/YU40259B/en unknown
- 1975-04-01 ES ES436175A patent/ES436175A1/en not_active Expired
- 1975-04-02 EG EG75195A patent/EG12263A/en active
- 1975-04-02 JP JP50040227A patent/JPS6042202B2/en not_active Expired
- 1975-04-02 SU SU752121601A patent/SU743561A3/en active
- 1975-04-02 EG EG194/75A patent/EG11640A/en active
- 1975-04-02 CS CS7500002240A patent/CS183789B2/en unknown
- 1975-04-02 IE IE709/75A patent/IE41777B1/en unknown
- 1975-04-02 TR TR18508A patent/TR18508A/en unknown
- 1975-04-02 TR TR18339A patent/TR18339A/en unknown
- 1975-04-02 JP JP4022675A patent/JPS5345364B2/ja not_active Expired
- 1975-04-02 RO RO106426A patent/RO84021B/en unknown
- 1975-04-02 PL PL1975179265A patent/PL98627B1/en unknown
- 1975-04-02 RO RO7581876A patent/RO79677A/en unknown
- 1975-04-02 IE IE708/75A patent/IE41140B1/en unknown
- 1975-04-02 SU SU752120455A patent/SU682096A3/en active
- 1975-04-02 CS CS7500002239A patent/CS183788B2/en unknown
- 1975-04-02 PL PL1975179266A patent/PL97786B1/en unknown
- 1975-11-05 SU SU752186207A patent/SU628812A3/en active
-
1976
- 1976-04-05 SU SU762342705A patent/SU626690A3/en active
-
1978
- 1978-01-12 JP JP232778A patent/JPS53135964A/en active Granted
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