GB926234A - Phosphonic and thiophosphonic acid esters - Google Patents
Phosphonic and thiophosphonic acid estersInfo
- Publication number
- GB926234A GB926234A GB10946/60A GB1094660A GB926234A GB 926234 A GB926234 A GB 926234A GB 10946/60 A GB10946/60 A GB 10946/60A GB 1094660 A GB1094660 A GB 1094660A GB 926234 A GB926234 A GB 926234A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carbon atoms
- alkyl
- radical
- radical containing
- grouping
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000002253 acid Substances 0.000 title abstract 3
- 150000002148 esters Chemical class 0.000 title abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 19
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- -1 thioketo compound Chemical class 0.000 abstract 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 230000000749 insecticidal effect Effects 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 229930194542 Keto Natural products 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 238000007865 diluting Methods 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 239000003995 emulsifying agent Substances 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 125000000468 ketone group Chemical group 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 1
- 229920000151 polyglycol Polymers 0.000 abstract 1
- 239000010695 polyglycol Substances 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing heterocyclic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4018—Esters of cycloaliphatic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4078—Esters with unsaturated acyclic alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/650905—Six-membered rings having the nitrogen atoms in the positions 1 and 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/6512—Six-membered rings having the nitrogen atoms in positions 1 and 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having three nitrogen atoms as the only ring hetero atoms
- C07F9/6518—Five-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention comprises phosphonic and thiophosphonic acid esters of the general formula:-(R1)(R2O)P(X)YA wherein R1 is an unsubstituted or substituted phenyl radical, an alkyl radical containing up to 8 carbon atoms, an alkenyl radical, an ethoxyvinyl radical or a cycloalkyl radical, R2 is an alkyl radical containing up to 4 carbon atoms, X and Y stand for oxygen or sulphur atoms and A stands for the grouping (a):-C(R4)=CH-R3 wherein R4 is an alkyl or alkoxy radical containing up to 4 carbon atoms and R3 is a cyano or alkyl-carbonyl group, the alkyl radical of which contains up to 4 carbon atoms, or when R4 is an alkoxy radical containing up to 4 carbon atoms R3 may also stand for an aminocarbonyl or alkoxycarbonyl group, the alkoxy radical of which contains up to 4 carbon atoms; or for the grouping: (b):- <FORM:0926234/IV(a)/1> wherein R5 is an alkyl radical containing up to 4 carbon atoms, R6 is an alkyl radical containing up to 4 carbon atoms or an alkylmercapto radical containing up to 4 carbon atoms, or the grouping:-(c): <FORM:0926234/IV(a)/2> wherein R7 is a hydrogen atom or an alkyl radical containing up to 4 carbon atoms and R8 is a hydrogen atom, an alkyl radical containing up to 4 carbon atoms or a phenyl radical,; or the grouping:-(d): <FORM:0926234/IV(a)/3> wherein R9 and R10 are alkyl radicals containing up to 4 carbon atoms. They may be obtained by reacting an appropriate enolisable keto or thioketo compound with an appropriate O-alkyl thionophosphonic acid halide or phosphonic acid halide. The reaction is preferably carried out with the alkali metal salts of the enolic compounds or by using the enolic compounds in the presence of alkali metal hydroxides, preferably in an inert organic solvent at room temperature or at slightly elevated temperature. Several examples are given typical products being:- <FORM:0926234/IV(a)/4> The products have insecticidal properties (see Group VI).ALSO:An insecticidal composition contains, in conjunction with an inert solid or liquid diluent or carrier, a compound of the general formula (R1)(R2O)P(X)YA wherein R1 is an unsubstituted or substituted phenyl radical, an alkyl radical containing up to 8 carbon atoms, or an alkenyl, ethoxyvinyl or cycloalkyl radical, R2 is a C1-C4 alkyl radical, X and Y are oxygen or sulphur atoms and A stands for the grouping (a)-C(R4) = CH-R3 wherein R4 is an alkyl or alkoxy radical containing up to 4 carbon atoms and R3 is a cyano group or alkylcarbonyl group the alkyl radical of which contains up to 4 carbon atoms, or when R4 is an alkoxy radical containing up to 4 carbon atoms R3 may also stand for an aminocarbonyl or alkoxycarbonyl group, the alkoxy radical of which contains up to 4 carbon atoms; or for the grouping <FORM:0926234/VI/1> wherein R5 is a C1-C4 alkyl radical, R6 is a C1-C4 alkyl radical or an alkylmercapto radical containing up to 4 carbon atoms; or for the grouping <FORM:0926234/VI/2> wherein R7 is a hydrogen atoms or C1-C4 alkyl radical and R8 is a hydrogen atom, an alkyl radical containing up to 4 carbon atoms or a phenyl radical; or for the grouping <FORM:0926234/VI/3> wherein R9 and R10 are C1-C4 alkyl radicals (see Group IV (b)). A typical composition is obtained by mixing the compound <FORM:0926234/VI/4> with acetone, adding benzoyl hydroxy diphenyl polyglycol ether as emulsifier and then diluting with water.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF28060A DE1140580B (en) | 1959-03-28 | 1959-03-28 | Process for the preparation of thionophosphonic acid esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB926234A true GB926234A (en) | 1963-05-15 |
Family
ID=7092725
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB10946/60A Expired GB926234A (en) | 1959-03-28 | 1960-03-28 | Phosphonic and thiophosphonic acid esters |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3216894A (en) |
| BE (1) | BE589122A (en) |
| CH (1) | CH387004A (en) |
| DE (1) | DE1140580B (en) |
| GB (1) | GB926234A (en) |
| NL (2) | NL126404C (en) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1445758A1 (en) * | 1964-03-26 | 1969-02-13 | Bayer Ag | Process for the production of thiophosphorus (phosphonic, - phosphine) or dithiophosphorus (- phosphonic, - phosphine) acid esters |
| US3336314A (en) * | 1964-12-02 | 1967-08-15 | Mobil Oil Corp | O-quinolinyl s-alkyl-alkylphos-phonodithioates |
| US3880997A (en) * | 1965-05-26 | 1975-04-29 | Bayer Ag | Insecticidal and acaricidal phosphorous-containing esters of 2-hydroxyquinoxaline |
| US3384540A (en) * | 1965-07-14 | 1968-05-21 | Stauffer Chemical Co | Pesticidal compositions and methods containing phosphorous-containing esters of 2-thiomethyl mercapto pyrimidines |
| DE1567137C3 (en) * | 1965-08-20 | 1979-01-25 | Sankyo Co. Ltd., Tokio | Phosphoric isoxazolyester-based insecticidal agent |
| US3775057A (en) * | 1969-02-24 | 1973-11-27 | Petrolite Corp | Use as corrosion inhibitors, nitrogen-heterocyclic phosphonates |
| DE1912972A1 (en) * | 1969-03-14 | 1970-10-01 | Bayer Ag | Phosphorus, phosphonic or thionophosphorus (phosphonic) acid esters and process for their preparation |
| DE1917741B2 (en) * | 1969-04-05 | 1976-12-02 | Bayer Ag, 5090 Leverkusen | (THIONO) PHOSPHORUS (PHOSPHONE) -AEUREESTER OR -ESTERAMIDE, THE METHOD OF MANUFACTURING AND USING THEM |
| US3952098A (en) * | 1970-07-30 | 1976-04-20 | Bayer Aktiengesellschaft | Compositions and methods of combatting insects and acarids using pyrazolo-(thiono)-phosphoric(phosphonic) acid esters |
| DE2049692A1 (en) * | 1970-10-09 | 1972-04-13 | Farbenfabriken Bayer Ag, 5090 Leverkusen | Pyrazolo (thiono) phosphorus (phosphonic) acid esters, process for their preparation and their use as insecticides and acaricides |
| DE2150169A1 (en) * | 1970-10-22 | 1972-04-27 | Agripat Sa | New esters |
| DE2150098C3 (en) * | 1970-10-22 | 1981-05-07 | Agripat S.A., Basel | 1,2,4-Triazolyl-3-phosphoric acid esters, their preparation and pesticides containing them |
| US3880584A (en) * | 1971-08-19 | 1975-04-29 | Petrolite Corp | Use as corrosion inhibitors:acridine phosphoric compounds |
| US3888626A (en) * | 1971-08-19 | 1975-06-10 | Petrolite Corp | Use as corrosion inhibitors: phenanthridine phosphonic compounds |
| BE792449A (en) * | 1971-12-10 | 1973-06-08 | Ciba Geigy | TRIAZOLYL ESTERS OF OXYGENIC ACIDS OF PHOSPHORUS AND PESTICIDE PRODUCTS THAT CONTAIN |
| DE2343931A1 (en) * | 1973-08-31 | 1975-04-03 | Bayer Ag | PYRIMIDINE (4) -YL- (THIONO) - (THIOL) -PHOSPHORUS (PHOSPHONE) -AEUREESTER OR. -ESTERAMIDE, THE PROCESS FOR THEIR MANUFACTURING AND THEIR USE AS INSETICIDES AND ACARICIDES |
| US4035487A (en) * | 1973-09-10 | 1977-07-12 | Ciba-Geigy Corporation | Pesticidal 2-phenyl-1,2,3-triazolyl-(4) and-triazox-(1)-yl-(4) phosphate and thiosphosphate esters |
| DE2431848A1 (en) * | 1974-07-02 | 1976-01-22 | Bayer Ag | IMIDAZOLYL- (THIONO) -PHOSPHORUS (PHOSPHONE) -AEUREESTER OR. -ESTERAMIDE, THE PROCESS FOR THEIR MANUFACTURING AND THEIR USE AS INSECTICIDE, ACARICIDE AND NEMATICIDE |
| DE2440677A1 (en) * | 1974-08-24 | 1976-03-04 | Bayer Ag | PYRIMIDINYLTHIONOPHOSPHONIC ACID ESTERS, PROCESS FOR THEIR PRODUCTION AND USE AS INSECTICIDES, ACARICIDES AND NEMATICIDES |
| DE2523324A1 (en) * | 1975-05-27 | 1976-12-09 | Bayer Ag | PYRIMIDINE (4,6) DIYL-BIS- (THIONO) (THIOL) PHOSPHORUS (PHOSPHONE) ACID ESTER, PROCESS FOR THEIR PRODUCTION AND THEIR USE AS INSECTICIDES AND ACARICIDES |
| DE2619450A1 (en) * | 1976-05-03 | 1977-11-24 | Bayer Ag | DIPHOSPHORYLATED PYRIMIDINS, THE PROCESS FOR THEIR MANUFACTURING AND THEIR USE AS INSECTICIDES AND ACARICIDES |
| DE2622501A1 (en) * | 1976-05-20 | 1977-12-08 | Bayer Ag | SULFONYLOXYPYRIMIDINYL (THIONO) (THIOL) -PHOSPHORUS- (PHOSPHONE) -AEUREESTER OR. -ESTERAMIDE, METHOD OF MANUFACTURING AND USING THEY AS INSECTICIDES AND ACARICIDES |
| DE2639258A1 (en) * | 1976-09-01 | 1978-03-02 | Bayer Ag | TERT.-BUTYL-SUBSTITUTED PYRAZOLYL (THIONO) (THIOL) -PHOSPHOR (PHOSPHON) -ACIDESTERS OR. -ESTERAMIDES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS INSECTICIDES, ACARICIDES AND NEMATICIDES |
| DE2639433A1 (en) * | 1976-09-02 | 1978-03-09 | Bayer Ag | PYRIMIDINYL (THIONO) (THIOL) -PHOSPHOR (PHOSPHON) ACID ESTER, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS INSECTICIDES AND ACARICIDES |
| AU511744B2 (en) * | 1976-09-25 | 1980-09-04 | Bayer Aktiengesellschaft | Pyrimidin(5)yl-(thiono) (thiol) phosporic-(phosphonic) acid esters and ester-amides |
| DE2703310A1 (en) * | 1977-01-27 | 1978-08-03 | Bayer Ag | SUBSTITUTED PYRIMIDINYL (THIO) - PHOSPHOR (PHOSPHON) ACID ESTERS OR. -ESTERAMIDES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS INSECTICIDES, ACARICIDES AND NEMATICIDES |
| US4104375A (en) * | 1977-02-24 | 1978-08-01 | Stauffer Chemical Company | Isoxazole phosphates and phosphonates |
| DE2831165A1 (en) * | 1978-07-15 | 1980-01-24 | Bayer Ag | 2-CYCLOPROPYL-PYRIMIDINE (4) YL-THIONOPHOSPHONIC ACID ESTER, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS INSECTICIDES AND ACARICIDES |
| DE3729263A1 (en) * | 1987-09-02 | 1989-03-23 | Bayer Ag | THIONOPHOSPHONIC ACID ESTER |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE510817A (en) * | 1951-04-20 | 1900-01-01 | ||
| US2867646A (en) * | 1956-04-09 | 1959-01-06 | Shell Dev | Complex arylphosphonates |
| BE568698A (en) * | 1957-06-24 |
-
0
- BE BE589122D patent/BE589122A/xx unknown
- NL NL249896D patent/NL249896A/xx unknown
- NL NL126404D patent/NL126404C/xx active
-
1959
- 1959-03-28 DE DEF28060A patent/DE1140580B/en active Pending
-
1960
- 1960-03-24 CH CH332360A patent/CH387004A/en unknown
- 1960-03-25 US US17487A patent/US3216894A/en not_active Expired - Lifetime
- 1960-03-28 GB GB10946/60A patent/GB926234A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE589122A (en) | 1900-01-01 |
| CH387004A (en) | 1965-01-31 |
| NL126404C (en) | 1900-01-01 |
| DE1140580B (en) | 1962-12-06 |
| US3216894A (en) | 1965-11-09 |
| NL249896A (en) | 1900-01-01 |
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