NO130107B - - Google Patents
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- NO130107B NO130107B NO00165916A NO16591666A NO130107B NO 130107 B NO130107 B NO 130107B NO 00165916 A NO00165916 A NO 00165916A NO 16591666 A NO16591666 A NO 16591666A NO 130107 B NO130107 B NO 130107B
- Authority
- NO
- Norway
- Prior art keywords
- pyrazinyl
- phosphorothioate
- diethyl
- soil
- tomato
- Prior art date
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- -1 phosphate ester Chemical class 0.000 claims description 11
- 241000244206 Nematoda Species 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 14
- 239000002689 soil Substances 0.000 description 14
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 14
- 240000003768 Solanum lycopersicum Species 0.000 description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 11
- HUTNOYOBQPAKIA-UHFFFAOYSA-N 1h-pyrazin-2-one Chemical compound OC1=CN=CC=N1 HUTNOYOBQPAKIA-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 241000196324 Embryophyta Species 0.000 description 7
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 230000001069 nematicidal effect Effects 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 235000013601 eggs Nutrition 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 235000013339 cereals Nutrition 0.000 description 3
- 239000000428 dust Substances 0.000 description 3
- 239000003337 fertilizer Substances 0.000 description 3
- 230000009545 invasion Effects 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 238000003892 spreading Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- FFOPEPMHKILNIT-UHFFFAOYSA-N Isopropyl butyrate Chemical compound CCCC(=O)OC(C)C FFOPEPMHKILNIT-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- KTXXEFQDZCVEQJ-UHFFFAOYSA-N dihydroxy-pyrazin-2-yloxy-sulfanylidene-$l^{5}-phosphane Chemical class OP(O)(=S)OC1=CN=CC=N1 KTXXEFQDZCVEQJ-UHFFFAOYSA-N 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000024121 nodulation Effects 0.000 description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 description 1
- WOYWLLHHWAMFCB-UHFFFAOYSA-N 2-ethylhexyl acetate Chemical compound CCCCC(CC)COC(C)=O WOYWLLHHWAMFCB-UHFFFAOYSA-N 0.000 description 1
- QPHGZSXJSJIEQN-UHFFFAOYSA-N 5,6-dimethyl-1h-pyrazin-2-one Chemical compound CC1=NC=C(O)N=C1C QPHGZSXJSJIEQN-UHFFFAOYSA-N 0.000 description 1
- SKZXVUPFUHQWKS-UHFFFAOYSA-N 6-chloro-1h-pyrazin-2-one Chemical compound OC1=CN=CC(Cl)=N1 SKZXVUPFUHQWKS-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical class OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 239000008365 aqueous carrier Substances 0.000 description 1
- 238000010936 aqueous wash Methods 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- ZDCHZHDOCCIZIY-UHFFFAOYSA-N phthalic acid;propane-1,2,3-triol Chemical class OCC(O)CO.OC(=O)C1=CC=CC=C1C(O)=O ZDCHZHDOCCIZIY-UHFFFAOYSA-N 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
- B65D33/00—Details of, or accessories for, sacks or bags
- B65D33/16—End- or aperture-closing arrangements or devices
- B65D33/25—Riveting; Dovetailing; Screwing; using press buttons or slide fasteners
- B65D33/2508—Riveting; Dovetailing; Screwing; using press buttons or slide fasteners using slide fasteners with interlocking members having a substantially uniform section throughout the length of the fastener; Sliders therefor
- B65D33/2516—Riveting; Dovetailing; Screwing; using press buttons or slide fasteners using slide fasteners with interlocking members having a substantially uniform section throughout the length of the fastener; Sliders therefor comprising tamper-indicating means, e.g. located within the fastener
- B65D33/2533—Riveting; Dovetailing; Screwing; using press buttons or slide fasteners using slide fasteners with interlocking members having a substantially uniform section throughout the length of the fastener; Sliders therefor comprising tamper-indicating means, e.g. located within the fastener the slide fastener being located between the product compartment and the tamper indicating means
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
- B65D31/00—Bags or like containers made of paper and having structural provision for thickness of contents
- B65D31/04—Bags or like containers made of paper and having structural provision for thickness of contents with multiple walls
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
- B65D33/00—Details of, or accessories for, sacks or bags
- B65D33/16—End- or aperture-closing arrangements or devices
Landscapes
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Bag Frames (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Laminated Bodies (AREA)
Description
Middel til bekjempelse av nematoder. Means for combating nematodes.
Foreliggende oppfinnelse vedrører eti middel som er virksomt til bekjempelse av nematoder. The present invention relates to an agent which is effective in combating nematodes.
Den aktive bestanddel i midlet er 0,0-dialkyl-o- (2-pyrazinyl) -f osf ortrionater, The active ingredient in the agent is 0,0-dialkyl-o-(2-pyrazinyl)-phosphorthrionate,
som representeres av følgende generelle which is represented by the following general
hvor R og R' er lavere alkylradikaler som methyl, ethyl, propyl og butyl, og X, Y og Z representerer hydrogen eller halogen eller fenyl- eller lavere alkylradikaler. De ovennevnte forbindelser kan lett fremstilles ved å la dialkylfosforkloridtioat av formelen hvor R og R' har den ovenfor angitte betydning, reagere med et hydroksypyrazin eller alkalimetallsalt herav av formelen where R and R' are lower alkyl radicals such as methyl, ethyl, propyl and butyl, and X, Y and Z represent hydrogen or halogen or phenyl or lower alkyl radicals. The above-mentioned compounds can be easily prepared by reacting dialkylphosphorus chloride thioate of the formula where R and R' have the above meaning with a hydroxypyrazine or alkali metal salt thereof of the formula
hvor X, Y og Z har den ovenfor angitte betydning, og A er hydrogen eller alkali-metall, i et inert oppløsningsmiddel. where X, Y and Z have the meaning given above, and A is hydrogen or alkali metal, in an inert solvent.
Reaksjonen kan utføres ved tempera-turer innenfor området av fra 10 til 100° The reaction can be carried out at temperatures within the range of from 10 to 100°
C og fortrinnsvis mellom 20 og 60° C. C and preferably between 20 and 60° C.
Når det frie hydroksypyrazin anvendes, utføres reaksjonen fortrinsvis i nær-vær av en hydrogenkloridakseptor, som al-kalimetall- og jordalkalimetallkarbonater. Ved fremstillingen av o,o-dietyl-o-(5,6-dietyl-2-pyrazinyl)-fosfortioat, kan reaksjonen f. eks. illustreres som følger: When the free hydroxypyrazine is used, the reaction is preferably carried out in the presence of a hydrogen chloride acceptor, such as alkali metal and alkaline earth metal carbonates. In the production of o,o-diethyl-o-(5,6-diethyl-2-pyrazinyl)-phosphorothioate, the reaction can e.g. is illustrated as follows:
Skikkete inerte oppløsningsmidler for reaksjonen omfatter vann, dimetylformamid, dioksan, N-metyl-2-pyrrolidon, ace-tonitril, benzen, toluen, xylen, de lavere alifatiske enverdige alkoholer, ketoner som aceton, metyletylketon, metyl-isobutylke-ton og cykloheksanon, og alifatiske estere som etylacetat, 2-etylheksylacetat, metyl-j propionat, etylbutyrat og isopropylbutyrat. Suitable inert solvents for the reaction include water, dimethylformamide, dioxane, N-methyl-2-pyrrolidone, acetonitrile, benzene, toluene, xylene, the lower aliphatic monohydric alcohols, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone, and aliphatic esters such as ethyl acetate, 2-ethylhexyl acetate, methyl propionate, ethyl butyrate and isopropyl butyrate.
Hydroksypyrazinene som anvendes ved The hydroxypyrazines used in
foreliggende fremgangsmåte, fremstilles lett ved reaksjon av a-aminokarboksylsyre-amider med 1,2-dikarbonylforbindelser i henhold til de fremgangsmåter som er be-skrevet i «Journal of the American Che-mical Society» 74, 1580—4 (1952). Reaksjonen av glycinamid med diacetyl for å dan-ne 2-hydroksy-5,6-dimetylpyrazin kan illustreres som følger: present method, is easily prepared by reaction of α-aminocarboxylic acid amides with 1,2-dicarbonyl compounds according to the methods described in "Journal of the American Chemical Society" 74, 1580-4 (1952). The reaction of glycinamide with diacetyl to form 2-hydroxy-5,6-dimethylpyrazine can be illustrated as follows:
Alkalimetallsaltene av hydroksypyrazinene kan fremstilles ved reaksjon av hy-droksypyrazinet med et alkalimetallhy-droksyd i vann efterfulgt av utfelning med etanol. The alkali metal salts of the hydroxypyrazines can be prepared by reaction of the hydroxypyrazine with an alkali metal hydroxide in water followed by precipitation with ethanol.
Dialkylfosforkloridtioatene som anvendes ved foreliggende fremgangsmåte kan fremstilles ved å la to mol ekvivalenter av en dialkylditiofosforsyre eller et alkalimetallsalt herav reagere med tre mol ekvivalenter av klor ved en temperatur av 0— 60° C. The dialkylphosphoric chloride thioates used in the present process can be prepared by allowing two mole equivalents of a dialkyldithiophosphoric acid or an alkali metal salt thereof to react with three mole equivalents of chlorine at a temperature of 0-60°C.
De følgende eksempler skal tjene til ytterligere å klargjøre oppfinnelsen. The following examples shall serve to further clarify the invention.
Eksempel 1. Example 1.
o,o-dietyl-o- (2-pyrazinyl) -f osf ortioat o,o-diethyl-o-(2-pyrazinyl)-phosphorthioate
Analyse: Analysis:
Beregnet: 12,48 pst. P. 11,29 pst. N. Funnet: 12,48 pst. P. 11,34 pst. N. Calculated: 12.48 percent P. 11.29 percent N. Found: 12.48 percent P. 11.34 percent N.
Eksempel 2. Example 2.
Eksempel 1 ble gjentatt under anvendelse av 175 ml av metylisobutylketon som oppløsningsmiddel i stedenfor N-metyl-2-Til et slam av 11,8 g (0,1 mol) av natriumsaltet av 2-hydroksypyrazin i 150 ml N-metyl-2-pyrrolidon, ble tilsatt under om-røring 18,9 g (0,1 mol) o,o-dietyl-fosfor-klortioat. Blandingens temperatur steg straks til 50° C og omrøringen ble fortsatt ved 40° C i 3 timer. Reaksjonsblandingen ble filtrert og utfelningen ble vasket med en liten del N-metyl-2-pyrrolidon. De for-ente filtrater ble konsentrert for å fjerne oppløsningsmidlet og den resulterende rest ble oppløst i 100 ml toluen. Toluenoppløs-ningen ble vasket med 10 pst.'s vandig natriumkarbonat og derpå med mettet na-triumkloridoppløsning til nøytralitet. Efter tørkning over vannfritt magnesiumsulfat ble toluenoppløsningen konsentrert i va-kuum og resten ble filtrert gjennom et Hyflo-magnesiumsulfatlag for å gi 19,9 g (73 pst. av teorien) av produktet, en klar ravfarvet væske med en brytningsindeks n^<5> 1.5131. Example 1 was repeated using 175 ml of methyl isobutyl ketone as solvent in place of N-methyl-2-To a slurry of 11.8 g (0.1 mol) of the sodium salt of 2-hydroxypyrazine in 150 ml of N-methyl-2- pyrrolidone, 18.9 g (0.1 mol) of o,o-diethyl phosphorous chlorothioate were added with stirring. The temperature of the mixture immediately rose to 50° C. and stirring was continued at 40° C. for 3 hours. The reaction mixture was filtered and the precipitate was washed with a small portion of N-methyl-2-pyrrolidone. The combined filtrates were concentrated to remove the solvent and the resulting residue was dissolved in 100 ml of toluene. The toluene solution was washed with 10% aqueous sodium carbonate and then with saturated sodium chloride solution to neutrality. After drying over anhydrous magnesium sulfate, the toluene solution was concentrated in vacuo and the residue was filtered through a pad of Hyflo magnesium sulfate to give 19.9 g (73 percent of theory) of the product, a clear amber liquid with a refractive index n^<5> 1.5131.
pyrrolidon. Ketonoppløsningsmidlet ble ikke erstattet med toluen før de vandige vaskninger. Utbyttet av produktet var 23,1 g (85 pst. av teorien). pyrrolidone. The ketone solvent was not replaced with toluene before the aqueous washes. The yield of the product was 23.1 g (85 percent of theory).
Fosfatesterne i de eksempler som er oppført i den følgende tabell, ble fremstilt i henhold til fremgangsmåten efter eksempel 1 under anvendelse av ekvimolare mengder av dialkylfosforkloridtioatet og alkalimetallsaltet av hydroksypyrazin. The phosphate esters in the examples listed in the following table were prepared according to the method of example 1 using equimolar amounts of the dialkyl phosphorous chloride thioate and the alkali metal salt of hydroxypyrazine.
Eksempel 7. Example 7.
o,o-dietyl-o-(6-klor-2-pyrazinyl) fosfortioat o,o-diethyl-o-(6-chloro-2-pyrazinyl) phosphorothioate
Til et slam av 13,5 g (0,1 mol) 6-klor-2-hydroksypyrazin og 10,6 g (0,1 mol) natriumkarbonat i 175 ml dimetylformamid, ble tilsatt under omrøring 18,9 g o,o-dietyl-fos-forkloridtioat. Blandingen ble opphetet ved 40—45° C i en periode av 3 timer. 22,6 gl To a slurry of 13.5 g (0.1 mol) of 6-chloro-2-hydroxypyrazine and 10.6 g (0.1 mol) of sodium carbonate in 175 ml of dimethylformamide, 18.9 g of o,o-diethyl -phos-for chloride thioate. The mixture was heated at 40-45° C. for a period of 3 hours. 22.6 gl
(80 pst. av teorien) av fosfatesteren ble utvunnet fra reaksjonsblandingen ved den fremgangsmåte som er angitt i eksempel 1. Produktet var en klar oransje-farvet (80 percent of theory) of the phosphate ester was recovered from the reaction mixture by the procedure set forth in Example 1. The product was a clear orange-colored
25 væske med en brytningsindeks nD 1.5187. 25 liquid with a refractive index nD 1.5187.
Analyse: Analysis:
Fosfatestrene i eksemplene som er opp-ført i den følgende tabell, ble fremstilt i henhold til fremgangsmåten efter eksempel 7 under anvendelse av ekvimolare mengder av dialkylfosforkloridtioat, hydroksypyrazin og natriumkarbonat. The phosphate esters in the examples listed in the following table were prepared according to the method according to example 7 using equimolar amounts of dialkyl phosphorus chloride thioate, hydroxypyrazine and sodium carbonate.
Andre typiske nematodicide forbindelser er: 0,0-dimetyl-O- (2-pyrazinyl) - Other typical nematocidal compounds are: 0,0-dimethyl-O-(2-pyrazinyl)-
fosfortioat phosphorothioate
0,0-dibutyl-O- (2-pyrazinyl) -fosfortioat 0,0-dibutyl-O- (6-klor-2-pyrazinyl) - 0,0-dibutyl-O-(2-pyrazinyl)-phosphorothioate 0,0-dibutyl-O-(6-chloro-2-pyrazinyl)-
fosfortioat phosphorothioate
0,0-dietyl-O- (5-fenyl-2-pyrazinyl) - 0,0-diethyl-O-(5-phenyl-2-pyrazinyl)-
fosfortioat phosphorothioate
0,0-dietyl-O- (5,6-dif enyl-2-pyrazinyl) - 0,0-diethyl-O-(5,6-diphenyl-2-pyrazinyl)-
fosfortioat phosphorothioate
0,0-dimetyl-0-(5,6-difenyl-2-pyrazinyl)-fosfortioat 0,0-dimethyl-0-(5,6-diphenyl-2-pyrazinyl)-phosphorothioate
0,0-dietyl-O- (6-brom-2-pyrazinyl) - 0,0-diethyl-O-(6-bromo-2-pyrazinyl)-
fosfortioat phosphorothioate
0,0-dietyl-O- (3-f enyl-2-pyrazinyl) - 0,0-diethyl-O-(3-phenyl-2-pyrazinyl)-
fosfortioat phosphorothioate
0,0-dietyl-0-(5,6-dietyl-2-pyrazinyl)-fosfortioat 0,0-diethyl-0-(5,6-diethyl-2-pyrazinyl)-phosphorothioate
0,0-dietyl-O-(3-klor-5,6-dimetyl-2-pyrazinyl) -fosfortioat 0,0-dietyl-O-(3-etyl-5,6-diklor-2-pyrazinyl) -fosfortioat 0,0-dimetyl-0-(5,6-dietyl-2-pyrazinyl)-fosfortioat 0,0-diethyl-O-(3-chloro-5,6-dimethyl-2-pyrazinyl)-phosphorothioate 0,0-diethyl-O-(3-ethyl-5,6-dichloro-2-pyrazinyl)-phosphorothioate 0,0-dimethyl-0-(5,6-diethyl-2-pyrazinyl)-phosphorothioate
0,0-dimetyl-O- (3-isopropyl-2-pyrazinyl) - 0,0-dimethyl-O-(3-isopropyl-2-pyrazinyl)-
fosfortioat phosphorothioate
0,0-dimetyl-O- (6-klor-2-pyrazinyl) - 0,0-dimethyl-O-(6-chloro-2-pyrazinyl)-
fosfortioat phosphorothioate
0,0-diisopropyl-O-(5-etyl-2-pyrazinyl)-fosfortioat 0,0-diisopropyl-O-(5-ethyl-2-pyrazinyl)-phosphorothioate
0,0-dipropyl-0-(3-fenyl-2-pyrazinyl)-fosfortioat 0,0-dipropyl-0-(3-phenyl-2-pyrazinyl)-phosphorothioate
0,0-dibutyl-O-(3,5,6-trimetyl-2-pyrazinyl)-fosfortioat 0,0-dibutyl-O-(3,5,6-trimethyl-2-pyrazinyl)-phosphorothioate
0,0-dibutyl-O- (6-brom-2-pyrazinyl) - 0,0-dibutyl-O-(6-bromo-2-pyrazinyl)-
fosfortioat phosphorothioate
0,0-diisopropyl-O- (2-pyrazinyl) - 0,0-diisopropyl-O-(2-pyrazinyl)-
fosfortioat phosphorothioate
0,0-diisopropyl-O- (5-metyl-2-pyrazinyl) - 0,0-diisopropyl-O-(5-methyl-2-pyrazinyl)-
fosfortioat. phosphorothioate.
Når fosfortioatesterene anvendes som nematodicide preparater, kan de påføres jorden alene eller de kan fremstilles som korn for påføring med en vanlig gjødnings-middelspredeinnretning, som er emulger-bart konsentrat eller fuktbart pulver for påføring med spredningsinnretningen, som When the phosphorus thioesters are used as nematocidal preparations, they can be applied to the soil alone or they can be prepared as grains for application with a conventional fertilizer spreading device, which is an emulsifiable concentrate or wettable powder for application with the spreading device, which
et støv for påføring med en vanlig for-støvningsinnretning eller adsorberes på a dust for application with a conventional atomizing device or adsorbed onto
aktivt kullstoff for påføring på frø. Da esterene har relativt lave damptrykk, kan de fremstilles i form av emulgerbare kon-sentrater som er skikket for tilsetning til overrislingsvann eller lignende. activated carbon for seed application. As the esters have relatively low vapor pressures, they can be produced in the form of emulsifiable concentrates which are suitable for addition to sprinkler water or the like.
Det er en fordel ved foreliggende oppfinnelse at de nematodicide forbindelser som er angitt ovenfor, er effektive når de It is an advantage of the present invention that the nematicidal compounds indicated above are effective when they
anvendes i fortynnete konsentrasjoner. Det used in diluted concentrations. The
er derfor å foretrekke å innføre forbindelsene i forskjellige slags skikkete inerte faste eller flytende bæremidler eller for-tynningsmidler. Slike preparater kan fremstilles enten som en suspensjon i et pas-sende ikke-oppløsningsmiddel, eller som et støvformet produkt. En suspensjon eller dispersjon av den nematodicide forbindelse i et ikke-oppløsningsmiddel som f. eks. it is therefore preferable to introduce the compounds in various kinds of suitable inert solid or liquid carriers or diluents. Such preparations can be prepared either as a suspension in a suitable non-solvent, or as a powdered product. A suspension or dispersion of the nematicidal compound in a non-solvent such as e.g.
vann, kan fremstilles for direkte tilføring til infisert jord. Alternativt kan en fremstilt suspensjon av forbindelsen modifise-res ved at den tilsettes små mengder, van- water, can be prepared for direct application to infected soil. Alternatively, a prepared suspension of the compound can be modified by adding small amounts,
ligvis fra ca. 1 til 5 deler, av et i handelen tilgjengelig dispergerings- eller overflate-aktivt middel pr. 100 deler av den nematodicide forbindelse. Eksempler på overflate-aktive forbindelser er: natriumsaltet av polymerisert propylnaftylensulfonsyre, en alkylarylpolyeteralkohol og en modifisert ftalsyreglycerolalkydharpiks. probably from approx. 1 to 5 parts, of a commercially available dispersing or surface-active agent per 100 parts of the nematocidal compound. Examples of surface-active compounds are: the sodium salt of polymerized propylene sulfonic acid, an alkyl aryl polyether alcohol and a modified phthalic acid glycerol alkyd resin.
Ved fremstillingen av pulverformete eller støvformete produkter kan den nematodicide forbindelse blandes med et findelt inert kornformet material som bæremiddel på hvilken som helst vanlig måte. Nyttige bæremidler omfatter kaolin, bentonit, tal-kum, pimpsten, kiselsyre, kalk, tremel, ful-lerjord, aktivert kull, benkull og lignende. Følgende eksempler skal ytterligere tjene til å klargjøre oppfinnelsen. In the manufacture of powdered or dusted products, the nematicidal compound can be mixed with a finely divided inert granular material as a carrier in any conventional manner. Useful carriers include kaolin, bentonite, talc, pumice, silicic acid, lime, wood flour, fuller's earth, activated charcoal, bone charcoal and the like. The following examples shall further serve to clarify the invention.
Eksempel 10. Example 10.
Fire ml alikvote deler av pyrazinylfosfortioatene i vann ved konsentrasjoner av Four ml aliquots of the pyrazinyl phosphorothioates in water at concentrations of
0,1, 0,01 og 0,001 pst. ble anbrakt i ampul-ler. Til hver ampulle ble tilsatt 100 An-guillula nematoder. Ampullene ble rotert i 20 timer og deretter ble det foretatt døde-lighetstellinger, som er oppført i tabell 1 0.1, 0.01 and 0.001 percent were placed in ampoules. 100 An-guillula nematodes were added to each ampoule. The ampoules were rotated for 20 hours and then mortality counts were made, which are listed in Table 1
Eksempel 11. Example 11.
Pyrazinylfosfortioatene ble blandet omhyggelig i jorden enten som et kornformet produkt eller i et vandig bæremiddel i mengder ikke overskridende 22,7 kg av den aktive bestanddel pr. 4,05 mål. Efter at forbindelsene var iblandet i jorden, ble der tilsatt under ytterligere blanding en alikvot del av ålormlarver (caconema), egg og rotknutevev. Den behandlete infiserte jord ble derpå anbrakt i blomsterpotter i et drivhus med 27° C. Den følgende dag ble en tomatfrøplante anbrakt i hver blom-sterpotte. Efter henstand i en periode av 45 dager ble tomatplanterøttene vasket fri for jord og vurdert i henhold til de tilstede-værende ålormrotknuter. Den følgende rot-knute-indeks ble anvendt: 0 = fullstendig fravær av rotknuter, 1 = 1—10 rotknuter og 2 = alvorlig rotknutedannelse. De opp-nådde resultater er vist i tabell 2. The pyrazinyl phosphorothioates were carefully mixed into the soil either as a granular product or in an aqueous carrier in quantities not exceeding 22.7 kg of the active ingredient per 4.05 goals. After the compounds had been mixed into the soil, an aliquot of eelworm larvae (caconema), eggs and root nodule tissue were added during further mixing. The treated infected soil was then placed in flower pots in a greenhouse at 27° C. The following day, a tomato seedling was placed in each flower pot. After standing for a period of 45 days, the tomato plant roots were washed free of soil and assessed according to the presence of eelworm root nodules. The following root nodule index was used: 0 = complete absence of root nodules, 1 = 1-10 root nodules and 2 = severe root nodule formation. The results achieved are shown in table 2.
Eksempel 12. Example 12.
Jordflater av en størrelse av 9,2 dm<2 >som inneholdt ålormegg og larver ble behandlet med 0,0-dietyl-O-(2-pyrazinyl)-fosfortioat absorbert på 30—60 maskers kornformet «Celite» (saltvanns diatomé-jord) i en mengde av 2,3 kg og 4,5 kg av fosfortioat pr. 4,05 mål. Kornene ble inn-arbeidet i jorden med et håndlukeredskap for mest mulig å komme nær en vanlig be-handling i praksis. Tomatfrøplanter ble straks plantet. Soil surfaces of a size of 9.2 dm<2 >containing eelworm eggs and larvae were treated with 0,0-diethyl-O-(2-pyrazinyl)-phosphorothioate absorbed on 30-60 mesh granular "Celite" (saline diatomaceous earth ) in an amount of 2.3 kg and 4.5 kg of phosphorothioate per 4.05 goals. The grains were worked into the soil with a hand weeding tool to get as close as possible to a normal treatment in practice. Tomato seedlings were immediately planted.
Omtrent fire uker efter behandlingen og derefter hver uke ble en tomatplante løftet opp og røttene undersøkt med hen-syn til ålormrotknuter. Ingen rotknuter ble funnet på noen av plantene fra jord-stykkene som var behandlet med 0,0-dietyl-0-(2-pyrazinyl)-fosfortioat, skjønt planter fra ikke-behandlete jordstykker var utsatt for en alvorlig rotknutedannelse. Approximately four weeks after the treatment and then every week, a tomato plant was lifted up and the roots examined for eelworm root nodules. No root nodules were found on any of the plants from the plots treated with 0,0-diethyl-0-(2-pyrazinyl)-phosphorothioate, although plants from untreated plots were subject to severe root nodulation.
De arter korn som ble anvendt ved dette forsøk, kan påføres jorden med hvil-ke som helst vanlige gjødningsmiddelspre-deapparater. Resultatene av forsøket viser at et kornformet preparat av fosfortioatet kan iblandes i jorden med tilstrekkelig jevnhet ved hjelp av mekanisk utstyr så at man får en utmerket bekjempelse av ålorm. The types of grain that were used in this experiment can be applied to the soil with any common fertilizer spreader. The results of the experiment show that a granular preparation of the phosphorus thioate can be mixed into the soil with sufficient uniformity by means of mechanical equipment so that an excellent control of eelworms is obtained.
Eksempel 13. Example 13.
I IN
Jord i løkdyrkingskrukker med en dia-meter av 20 cm ble infisert med ålormlarver og egg, og påsprøytet med en vandig emulsjon av 0,0-dietyl-O-(2-pyrazinyl)-fosfortioat 24 timer før plantingen av ti tomatfrøplanter i hver krukke. Konsentra-sjonen av fosfortioatet var 0,5 pst. og til-føringsmengden var 325 liter væske pr. 4,05 mål. Dette svarer til 1,65 kg 0,0-dietyl-0-(2-pyrazinyl)-fosfortioat pr. 4,05 mål. Dess-uten ble enkelte av krukkene tilført en ytterligere ekvivalent påsprøytning direkte over tomatfrøplantene en uke efter den første sprøytepåføring. Soil in onion-growing pots with a diameter of 20 cm was infested with eelworm larvae and eggs, and sprayed with an aqueous emulsion of 0,0-diethyl-O-(2-pyrazinyl)-phosphorothioate 24 hours before the planting of ten tomato seedlings in each pot . The concentration of the phosphorothioate was 0.5 per cent and the supply quantity was 325 liters of liquid per 4.05 goals. This corresponds to 1.65 kg of 0,0-diethyl-0-(2-pyrazinyl)-phosphorothioate per 4.05 goals. In addition, some of the pots were given a further equivalent spraying directly over the tomato seedlings one week after the first spraying.
Prosenttallet for planter som dukket opp efter 17 dager, prosenttallet av planter i vekst (stand) efter 40 dager og middels-høyden efter 25 dager ble målt og resultatene er angitt i tabell 3. The percentage of plants that emerged after 17 days, the percentage of plants in growth (stand) after 40 days and the average height after 25 days were measured and the results are shown in table 3.
52 dager efter plantningen av tomatfrøene ble der utført en avsluttende tel-ling av planter i vekst og sammenlignende prøver av friskhetstilstanden eller kraft ble foretatt når røttene av tomatplantene ble undersøkt. Resultatene er oppført i tabell 4. 52 days after planting the tomato seeds, a final count of growing plants was carried out and comparative samples of the state of freshness or vigor were carried out when the roots of the tomato plants were examined. The results are listed in Table 4.
Det er alminnelig kjent at en sterk invasjon av ålorm i røttene til frøplanter vil drepe dem eller svekke dem så snart at de i alt vesentlig blir verdiløse. Det frem-går av resultatene av dette forsøk at der oppnåes en utmerket beskyttelse av tomatplanter. It is common knowledge that a strong infestation of eelworms in the roots of seedlings will kill them or weaken them as soon as they become essentially worthless. It appears from the results of this experiment that an excellent protection of tomato plants is achieved.
Eksempel 14. Example 14.
Tomatfrø ble belagt med et aktivert kullstøv som inneholdt 50 pst. 0,0-dietyl- Tomato seeds were coated with an activated carbon dust containing 50 percent 0,0-diethyl-
0-(2-pyrazinyl)-fosfortioat i en mengde av 0,9 kg pr. 45 kg frø. 10 behandlete frø ble plantet i dyrkingskrukker med en diame-ter av 20 cm som inneholdt jord som var infisert med ålormlarver og egg. På lignende måte ble 10 ubehandlete tomatfrø-planter satt i den infiserte jord. Krukkene ble derpå overført til et drivhus med en temperatur av 27° C, hvor de forble så lenge forsøket varte. Resultatene er oppført i tabell 5. O-(2-pyrazinyl)-phosphorothioate in an amount of 0.9 kg per 45 kg of seeds. 10 treated seeds were planted in 20 cm diameter culture pots containing soil infested with eelworm larvae and eggs. In a similar manner, 10 untreated tomato seedlings were planted in the infected soil. The jars were then transferred to a greenhouse with a temperature of 27°C, where they remained for the duration of the experiment. The results are listed in Table 5.
Resultatene av de ubehandlete frø i den ovenfor anførte tabell viser at inva-sjonen av ålorm i tomatplanterøttene re-duserte antallet av planter i vekst drastisk. Skjønt der hadde funnet sted noen invasjon av ålorm i røttene av tomatplanter fra frø som var belagt med det aktiverte kullpreparat som inneholdt 0,0-dietyl-0-(2-pyrazinyl)-fosfortioat, så var denne invasjon meget liten og plantene viste en utmerket vekst ved slutten av forsøket. The results of the untreated seeds in the above-mentioned table show that the invasion of eelworms in the tomato plant roots drastically reduced the number of plants in growth. Although there had been some invasion of eelworms into the roots of tomato plants from seed coated with the activated carbon preparation containing 0,0-diethyl-0-(2-pyrazinyl)-phosphorothioate, this invasion was very slight and the plants showed a excellent growth at the end of the experiment.
De nematodicide forbindelser må anvendes i effektive mengder. Som bemerket The nematocidal compounds must be used in effective quantities. As noted
ovenfor, kan de påføres jorden på en ef-fektiv måte på forskjellige måter, som f. above, they can be applied to the soil in an effective way in different ways, such as
eks. i form av et støvformet produkt for e.g. in the form of a dust-shaped product for
tilføring ved hjelp av vanlige støvpåfør-ingsinnretninger, som en emulsjon for på-føring ved hjelp av spredningsinnretninger, application by means of conventional dust application devices, as an emulsion for application by means of spreading devices,
på kornformete produkter for påføring med on granular products for application with
en vanlig gjødningsmiddelspredeinnretning a common fertilizer spreader
eller absorbert på aktivert kullstoff for på-føring på frøene. Hvilken påføringsmetode or absorbed on activated carbon for application to the seeds. Which method of application
man enn anvender, så oppnåes der gode resultater ved å tilføre fosfortioatforbindel-sene i konsentrasjoner varierende fra ca. whichever is used, good results are achieved by adding the phosphorothioate compounds in concentrations varying from approx.
0,9 til ca. 23 kg pr. 4,05 mål. 0.9 to approx. 23 kg per 4.05 goals.
Claims (1)
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-
1966
- 1966-12-07 GB GB54744/66A patent/GB1125189A/en not_active Expired
- 1966-12-07 AT AT1128966A patent/AT268986B/en active
- 1966-12-08 SE SE16868/66A patent/SE314576B/xx unknown
- 1966-12-08 NO NO00165916A patent/NO130107B/no unknown
- 1966-12-09 FR FR86914A patent/FR1504276A/en not_active Expired
- 1966-12-09 US US607346A patent/US3473589A/en not_active Expired - Lifetime
- 1966-12-09 DK DK639866AA patent/DK120521B/en unknown
- 1966-12-09 NL NL6617372A patent/NL6617372A/xx unknown
- 1966-12-09 BE BE690947D patent/BE690947A/xx unknown
- 1966-12-09 LU LU52559D patent/LU52559A1/xx unknown
- 1966-12-10 FI FI663288A patent/FI51678C/en active
- 1966-12-12 CH CH1773366A patent/CH452430A/en unknown
Also Published As
Publication number | Publication date |
---|---|
CH452430A (en) | 1968-05-31 |
FI51678C (en) | 1977-03-10 |
BE690947A (en) | 1967-05-16 |
AT268986B (en) | 1969-02-25 |
US3473589A (en) | 1969-10-21 |
GB1125189A (en) | 1968-08-28 |
DK120521B (en) | 1971-06-07 |
NL6617372A (en) | 1967-06-12 |
FR1504276A (en) | 1967-12-01 |
FI51678B (en) | 1976-11-30 |
SE314576B (en) | 1969-09-08 |
LU52559A1 (en) | 1967-02-09 |
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