DE2637007A1 - ISOXAZOLYL (THIONO) (THIOL) -PHOSPHOR (PHOSPHON) -SAEESESTERS OR. -ESTERAMIDES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS INSECTICIDES - Google Patents
ISOXAZOLYL (THIONO) (THIOL) -PHOSPHOR (PHOSPHON) -SAEESESTERS OR. -ESTERAMIDES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS INSECTICIDESInfo
- Publication number
- DE2637007A1 DE2637007A1 DE19762637007 DE2637007A DE2637007A1 DE 2637007 A1 DE2637007 A1 DE 2637007A1 DE 19762637007 DE19762637007 DE 19762637007 DE 2637007 A DE2637007 A DE 2637007A DE 2637007 A1 DE2637007 A1 DE 2637007A1
- Authority
- DE
- Germany
- Prior art keywords
- spp
- tert
- butyl
- thiono
- iso
- 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.)
- Pending
Links
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- 238000002360 preparation method Methods 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
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- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
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- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
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- 229910017052 cobalt Inorganic materials 0.000 description 1
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- 239000000470 constituent Substances 0.000 description 1
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- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
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- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000002012 dioxanes Chemical class 0.000 description 1
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- 238000005538 encapsulation Methods 0.000 description 1
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- JRVYNNNVVQCNTG-UHFFFAOYSA-N ethoxy-(6-sulfanylidenecyclohexa-2,4-dien-1-yl)phosphinic acid Chemical compound CCOP(O)(=O)C1C=CC=CC1=S JRVYNNNVVQCNTG-UHFFFAOYSA-N 0.000 description 1
- VUYNTIDSHCJIKF-UHFFFAOYSA-N ethyl 4,4-dimethyl-3-oxopentanoate Chemical compound CCOC(=O)CC(=O)C(C)(C)C VUYNTIDSHCJIKF-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
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- 238000010438 heat treatment Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
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- 229910052742 iron Inorganic materials 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical class [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N methyl iso-propyl ketone Natural products CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
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- 239000011733 molybdenum Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
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- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
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- 239000011701 zinc Substances 0.000 description 1
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Classifications
-
- 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
- C07F9/6527—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and oxygen atoms as the only ring hetero atoms
- C07F9/653—Five-membered rings
-
- 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
- A01N57/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having alternatively specified atoms bound to the phosphorus atom and not covered by a single one of groups A01N57/10, A01N57/18, A01N57/26, A01N57/34
- A01N57/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having alternatively specified atoms bound to the phosphorus atom and not covered by a single one of groups A01N57/10, A01N57/18, A01N57/26, A01N57/34 containing heterocyclic radicals
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Biochemistry (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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
Zentralbereich Patente, Marken und LizenzenCentral area of patents, trademarks and licenses
5090 Leverkusen, Bayerwerk Hu/AB5090 Leverkusen, Bayerwerk Hu / AB
Isoxazolyl(thiono) (thiol)-phosphor(phosphon)-säureester bzw. -esteramide, Verfahren zu ihrer Herstellung und ihre Verwendung als InsektizideIsoxazolyl (thiono) (thiol) phosphorus (phosphonic) acid ester or esteramides, processes for their preparation and their use as insecticides
Die vorliegende Erfindung betrifft neue Isoxazolyl(thiono)-(thiol)-phosphor(phosphon)-säureester bzw. -esteramide, welche insektizide Eigenschaften haben und ein Verfahren zu ihrer Herstellung.The present invention relates to new isoxazolyl (thiono) (thiol) phosphorus (phosphonic) acid esters or ester amides, which have insecticidal properties and a process for their preparation.
Es ist bereits bekannt, daß 0,0-Dialkyl-O-isoxazolylthionophosphorsäureester, z.B. 0,0-Diäthyl-0-^3-methyl-isoxazol(5)yl7-thionophosphorsäureester, insektizide Eigenschaften besizten (vergleiche Deutsche Patentschrift 910 652).It is already known that 0,0-dialkyl-O-isoxazolylthionophosphoric acid ester, e.g. 0,0-diethyl-0- ^ 3-methyl-isoxazol (5) yl7-thionophosphoric acid ester, possessed insecticidal properties (see German Patent 910 652).
Es wurde nun gefunden, daß die neuen Isoxazolyl(thiono)(thiol)-phosphor(phosphon)-säureester bzw. -esteramide der FormelIt has now been found that the new isoxazolyl (thiono) (thiol) phosphorus (phosphonic) acid esters or ester amides of the formula
5 /OR1 5 / OR 1
AO-P \ 2 AO-P \ 2
Le A 17 393Le A 17 393
809808/0155809808/0155
in welcher ^f in which ^ f
R für Wasserstoff, Halogen, Alkyl oder Alkylthio,R for hydrogen, halogen, alkyl or alkylthio,
R1 für Alkyl,R 1 for alkyl,
R für Alkyl, Alkoxy, Alkylthio, Monoalkylamino oder Phenyl undR for alkyl, alkoxy, alkylthio, monoalkylamino or phenyl and
X für Sauerstoff oder Schwefel stehen,X stand for oxygen or sulfur,
sich durch eine starke insektizide Wirksamkeit auszeichnen.are characterized by a strong insecticidal effectiveness.
Weiterhin wurde gefunden, daß die neuen Isoxazolyl(thiono)-(thiol)-phosphor(phosphon)-säureester bzw. -esteramide der Formel (I) erhalten werden, wenn man 3-tert.-Butyl-5-hydroxyisoxazolderivate der FormelIt has also been found that the new isoxazolyl (thiono) - (thiol) -phosphorus (phosphonic) acid esters or ester amides of the formula (I) are obtained by using 3-tert-butyl-5-hydroxyisoxazole derivatives the formula
OHOH
in welcherin which
R die oben angegebene Bedeutung hat, gegebenenfalls in Gegen wart eines Säureakzeptors oder gegebenenfalls in Form der . Alkali-, Erdalkali- oder Ammoniumsalze mit (Thiono)(Thiol)-Phosphor(phosphon)-säureester- oder -esteramidhalogeniden der Formel R has the meaning given above, optionally in the presence of an acid acceptor or optionally in the form of . Alkali, alkaline earth or ammonium salts with (thiono) (thiol) phosphorus (phosphonic) acid ester or ester amide halides of the formula
ΪOR1 ΪOR 1
Ϊ/ORΪ / OR
Hai-p; P (in)Hai-p; P (in)
Le A 17 393 - 2 -Le A 17 393 - 2 -
809808/0166809808/0166
in welcherin which
1 2
R ,R und x die oben angegebene Bedeutung haben und1 2
R, R and x have the meaning given above and
Hai für Halogen, vorzugsweise Chlor, steht,Hai represents halogen, preferably chlorine,
gegebenenfalls in Gegenwart eines Lösungs- oder Verdünnungsmittels umsetzt.optionally in the presence of a solvent or diluent implements.
Überraschenderweise zeigen die erfindungsgemäßen Isoxazolyl-(thiono)(thiol)-phosphor(phosphon)-säureester bzw. -esteramide eine bessere insektizide Wirkung als der vorbekannte 0,0-Diäthyl-O-[3-methyl-isoxazol(5)yi]-thionophosphorsäureester analoger Konstitution und gleicher Wirkungsrichtung. Die Stoffe vorliegender Erfindung stellen somit eine echte Bereicherung der Technik dar.The isoxazolyl (thiono) (thiol) phosphorus (phosphonic) acid esters according to the invention surprisingly show or ester amides have a better insecticidal effect than the previously known 0,0-diethyl-O- [3-methyl-isoxazol (5) yi] -thionophosphoric acid ester analogous constitution and the same direction of action. The fabrics of the present invention are therefore a real asset of technology.
Verwendet man beispielsweise 3-tert.-Butyl-4-iso-propyl-5-hydroxy-isoxazol und O-Äthylthionophenylphosphonsäureesterchlorid als Ausgangsmaterialien, so kann der Reaktionsablauf durch das folgende Formelschema wiedergegeben werden: If, for example, 3-tert-butyl-4-iso-propyl-5-hydroxy-isoxazole and O-ethylthionophenylphosphonic acid ester chloride are used as starting materials, the course of the reaction can be represented by the following equation :
V0YV 0 Y
OH f, /OC9H1- SäureakzeptorOH f, / OC 9 H 1 - acid acceptor
+ Cl-P Ζ2 5 + Cl-P Ζ 2 5
tert.-C4H9^ ^C3H7-ISO \j) " HC1 tert. -C 4 H 9 ^ ^ C 3 H 7 -ISO \ j) " HC1
/1 ^c/ 1 ^ c
tert.-C/tert.-C /
Die zu verwendenden Ausgangsstoffe sind durch die Formeln (II) und (III) eindeutig definiert. Vorzugsweise stehen darin jedochThe starting materials to be used are clearly defined by the formulas (II) and (III). Preferably, however, it says
Le A 17 393 - 3 - Le A 17 393 - 3 -
809808/0155809808/0155
2637Q072637Q07
R für Wasserstoff, Chlor oder Alkylthio mit 1 bis 4, insbesondere lkjs 3, Kohlenstoffatomen,R stands for hydrogen, chlorine or alkylthio with 1 to 4, in particular lkj s 3, carbon atoms,
R für geradkettiges oder verzweigtes Alkyl mit 1 bis 6, insbesondere 1 bis 4, Kohlenstoffatomen,R for straight-chain or branched alkyl having 1 to 6, in particular 1 to 4, carbon atoms,
R für geradkettiges oder verzweigtes Alkoxy bzw. Alkylthio oder Monoalkylamino mitjelbjs 6, insbesondere 1 bis 4, Kohlenstoffatomen oder geradkettiges oder verzweigtes Alkyl mit 1 bis 4, insbesondere 1 bis 3, Kohlenstoffatomen undR stands for straight-chain or branched alkoxy or alkylthio or monoalkylamino with 6, in particular 1 to 4, Carbon atoms or straight or branched chain Alkyl having 1 to 4, in particular 1 to 3, carbon atoms and
X für Schwefel.X for sulfur.
Die als Ausgangsprodukte benötigten 3-tert.-Butyl-5-hydroxyisoxazolderivate (II) können nach literaturbekannten Verfahren hergestellt werden, indem man Hydroxylammoniumchlorid mit Pivaloylessigsäureesterderivaten gegebenenfalls in Gegenwart von Alkoholat umsetzt.The 3-tert-butyl-5-hydroxyisoxazole derivatives required as starting materials (II) can be prepared by processes known from the literature by using hydroxylammonium chloride Pivaloylessigsäureesterderivaten converts optionally in the presence of alcoholate.
Als Beispiele hierfür seien im einzelnen genannt: 4-Chlor-, 4-Methylthio-, 4-Äthylthio-, 4-n-Propylthio- und 4-iso-Propylthio-3-tert.-butyl-5-hydroxy-isoxazol und 3-tert.-Butyl-5-hydroxy-isoxazol. Examples include: 4-chloro, 4-methylthio, 4-ethylthio, 4-n-propylthio and 4-iso-propylthio-3-tert-butyl-5-hydroxy-isoxazole and 3-tert-butyl-5-hydroxy-isoxazole.
Die weiterhin als Ausgangsmaterialien benötigten (Thiono)(Thiol)· Phosphor(phosphon)-säureester- bzw. -esteramidhalogenide (III) sind bekannt und können nach literaturbekannten Verfahren hergestellt werden. Als Beispiele dafür seien im einzelnen genannt: 0,0-Dimethyl-, O,O-Diäthyl-, 0,0-Di-n-propyl-, 0,0-Di-isobutyl-, 0,0-Di-n-butyl-, 0,0-Di-iso-butyl-, 0,0-Di-sec.-butyl-, O-Methyl-0-äthyl-, O-Methyl-0-n-propyl-, O-Methyl-0-isopropyl-, O-Methyl-0-n-butyl-, O-Methyl-0-iso-butyl-, O-Methyl-0-sec.-butyl-, O-Äthyl-0-n-propyl-, O-Äthyl-0-iso-propyl-,The (thiono) (thiol) phosphorus (phosphonic) acid ester or ester amide halides (III) also required as starting materials are known and can be prepared by processes known from the literature. As B e ispiele it may be mentioned are: 0,0-dimethyl, O, O-diethyl, 0,0-di-n-propyl, 0,0-di-isobutyl, 0,0-di- n-butyl-, 0,0-di-iso-butyl-, 0,0-di-sec-butyl-, O-methyl-0-ethyl-, O-methyl-0-n-propyl-, O- Methyl-0-isopropyl-, O-methyl-0-n-butyl-, O-methyl-0-iso-butyl-, O-methyl-0-sec-butyl-, O-ethyl-0-n-propyl -, O-ethyl-0-iso-propyl-,
IM A 17 393 - 4 - IM A 17 393 - 4 -
809808/0155809808/0155
O-Äthyl-O-n-butyl-, O-Äthyl-0-sec.-butyl-, O-Äthyl-O-isobutyl-, O-n-Propyl-0-butyl- bzw. O-iso-Propyl-0-butyl (thiono)-phosphorsäurediesterchlorid, fernerO-ethyl-O-n-butyl-, O-ethyl-0-sec.-butyl-, O-ethyl-O-isobutyl-, O-n-propyl-0-butyl or O-iso-propyl-0-butyl (thiono) phosphoric acid diester chloride, further
O,S-Dimethyl-, O,S-Diäthyl-, 0,S-Di-n-propyl-, 0,S-Di-isopropyl-, O,S-Di-n-butyl-, 0,S-Di-iso-butyl-, O-Äthyl-Snpropyl-, O-Äthyl-S-iso-propyl-, O-Äthyl-Sn-butyl-, O-Äthyl-S-sec.-butyl-, O-n-Propyl-S-äthyl-, O-n-Propyl-S-iso-propyl-, O-n-Butyl-S-n-propyl- und O-sec.-Butyl-S-äthyl (thiono)thiolphosphorsäurediesterchlorid, außerdem O-Methyl-, O-Äthyl-, O-n-Propyl-, O-iso-Propyl-, O-n-Butyl-, O-iso-Butyl-, O-sec.-Butylmethan- bzw. -äthan-, -n-propan- und -iso-propan-(thiono)phosphorsäureesterchlorid und O-Methyl-N-methyl-, O-Methyl-N-äthyl-, O-Methyl-N-n-propyl-, O-Methyl-N-iso-propyl-, O-Äthyl-N-methyl-, O-Äthyl-N-äthyl-, O-Äthyl-N-n-propyl-, O-Äthyl-N-iso-propyl-, O-n-Propyl-N-methyl-, O-n-Propyl-N-äthyl-, O-n-Propyl-N-n-propyl-, O-n-Propyl-N-iso-propyl-, O-iso-Propyl-N-methyl-, O-iso-Propyl-N-äthyl-, O-iso-Propyl-N-n-propyl-, O-iso-Propyl-N-iso-propyl-, O-n-Butyl-N-methyl-, O-n-Butyl-N-äthyl-, O-n-Butyl-N-n-propyl-, O-n-Butyl-N-iso-propyl-, O-iso-Butyl-N-methyl-, O-iso-Butyl-N-äthyl-, O-iso-Butyl-N-n-propyl-, O-iso-Butyl-N-iso-propyl-, O-sec.-Butyl-N-methyl-, O-sec.-Butyl-N-äthyl-, O-sec.-Butyl-N-n-propyl- und O-sec.-Butyl-N-iso-propylthiondphosphorsäuremonoesteramidchlorid. O, S-dimethyl-, O, S-diethyl-, 0, S-di-n-propyl-, 0, S-di-isopropyl-, O, S-di-n-butyl-, 0, S-di-iso-butyl-, O-ethyl-snpropyl-, O-ethyl-S-iso-propyl-, O-ethyl-Sn-butyl-, O-ethyl-S-sec.-butyl-, O-n-propyl-S-ethyl-, O-n-propyl-S-iso-propyl-, O-n-Butyl-S-n-propyl- and O-sec.-Butyl-S-ethyl (thiono) thiolphosphoric acid diester chloride, also O-methyl, O-ethyl, O-n-propyl, O-iso-propyl, O-n-butyl, O-iso-butyl, O-sec-butyl methane or ethane, n-propane and -iso-propan (thiono) phosphoric acid ester chloride and O-methyl-N-methyl-, O-methyl-N-ethyl-, O-methyl-N-n-propyl-, O-methyl-N-iso-propyl-, O-ethyl-N-methyl-, O-ethyl-N-ethyl-, O-ethyl-N-n-propyl-, O-ethyl-N-iso-propyl-, O-n-propyl-N-methyl-, O-n-propyl-N-ethyl-, O-n-propyl-N-n-propyl-, O-n-propyl-N-iso-propyl-, O-iso-propyl-N-methyl-, O-iso-propyl-N-ethyl-, O-iso-propyl-N-n-propyl-, O-iso-propyl-N-iso-propyl-, O-n-Butyl-N-methyl-, O-n-Butyl-N-ethyl-, O-n-Butyl-N-n-propyl-, O-n-butyl-N-iso-propyl-, O-iso-butyl-N-methyl-, O-iso-butyl-N-ethyl-, O-iso-butyl-N-n-propyl-, O-iso-butyl-N-iso-propyl-, O-sec-butyl-N-methyl-, O-sec-butyl-N-ethyl-, O-sec-butyl-N-n-propyl- and O-sec-butyl-N-iso-propylthione phosphoric acid monoester amide chloride.
Das Verfahren zur Herstellung der erfindungsgemäßen Verbindungen wird bevorzugt unter Mitverwendung geeigneter Lösungs- und Verdünnungsmittel durchgeführt. Als solche kommen praktisch alle inerten organischen Solventien infrage. Hierzu gehören insbesondere aliphatische und aromatische, gegebenenfalls chlorierte Kohlenwasserstoffe, wie Benzol, Toluol, Xylol, Benzin, Methylenchlorid, Chloroform, Tetrachlorkohlenstoff, Chlorbenzol, oder Äther, z.B. Diäthyl- und Dibutyläther, Dioxane, ferner Ketone, beispielsweise Aceton, Methyläthyl-, Methylisopropyl- und Methylisobutylketon, außerdem Nitrile, wie Aceto- und Proplonitril. The process for the preparation of the compounds according to the invention is preferably carried out using suitable solvents and diluents. Practically all inert organic solvents can be used as such. These include, in particular, aliphatic and aromatic, optionally chlorinated hydrocarbons, such as benzene, toluene, xylene, gasoline, methylene chloride, chloroform, carbon tetrachloride, chlorobenzene, or ethers, e.g. diethyl and dibutyl ethers, dioxanes, and also ketones, e.g. acetone, methyl ethyl, methyl isopropyl and methyl isobutyl ketone, as well as nitriles such as aceto- and proponitrile.
*· A 17 393 * A 17 393
Als Säureakzeptoren können alle üblichen Säurebindemittel Verwendung finden. Besonders bewährt haben sich Alkalicarbonate und -alkoholate, wie Natrium- und Kaliumcarbonat, -methylat bzw. -äthylat und Kalium-tert.-butylat, ferner aliphatische, aromatische oder heterocyclische Amine, beispielsweise Triäthylamin, Trimethylamin, Dirnethylanilin, Dirnethylbenzylamin und Pyridin.All customary acid binders can be used as acid acceptors Find. Alkali carbonates and alcoholates, such as sodium and potassium carbonate and methylate, have proven particularly useful or ethylate and potassium tert-butylate, also aliphatic, aromatic or heterocyclic amines, for example triethylamine, Trimethylamine, dirnethylaniline, dirnethylbenzylamine and pyridine.
Die Reaktionstemperatur kann innerhalb eines größeren Bereichs c variiert werden. Im allgemeinen arbeitet man zwischen O und 10O0C, vorzugsweise bei Io bis 600C.The reaction temperature can be varied within a relatively wide range c. In general, the reaction is preferably carried out at between O and 10O 0 C, wherein Io 0 to 60 C.
Die Umsetzung läßt man im allgemeinen bei Normaldruck ablaufen.The reaction is generally allowed to proceed under normal pressure.
Zur Durchführung des Verfahrens setzt man die Ausgangsstoffe meist in äquimolarem Verhältnis ein. Ein Überschuß der einen oder anderen Komponente bringt keine wesentlichen Vorteile. Die Reaktionspartner werden meist in einem der oben angeführten Lösungsmittel in Gegenwart eines Säureakzeptor vereinigt und bei erhöhter Temperatur zur Vervollständigung der Reaktion eine oder mehrere Stunden gerührt. Nach dem Abkühlen versetzt man die Mischung mit einem organischen Lösungsmittel, z.B. Toluol, und arbeitet die organische Phase in üblicher Weise durch.Waschen, Trocknen und Abdestillieren des Lösungsmittels auf.The starting materials are used to carry out the process mostly in an equimolar ratio. An excess of one or the other component has no significant advantages. The reactants are usually combined in one of the solvents listed above in the presence of an acid acceptor and at an elevated temperature to complete the reaction stirred for one or more hours. After cooling, the mixture is mixed with an organic solvent, e.g. toluene, and the organic phase works in the usual way. Washing, drying and distilling off the Solvent.
Die neuen Verbindungen fallen in Form von ölen an, die sich meist nicht unzersetzt destillieren lassen, jedoch durch sogenanntes "Andestillieren", d.h. durch längeres Erhitzen unter vermindertem Druck auf mäßig erhöhte Temperaturen von den letzten flüchtigen Anteilen befreit und auf diese Weise gereinigt werden können. Zu ihrer Charakterisierung dient der Brechungsindex.The new compounds are obtained in the form of oils, which usually not allowed to distill undecomposed, but by so-called "partial distillation", i.e. by heating under for a longer period of time freed from the last volatile constituents under reduced pressure to moderately elevated temperatures and purified in this way can be. The refractive index is used to characterize them.
Wie bereits mehrfach erwähnt, zeichnen sich die erfindungsgemäßen IsoxazolylCthionoKthiolJ-phosphoriphosphonJ-säure-As already mentioned several times, the isoxazolylCthionoKthiolJ-phosphoriphosphonicJ-acid-
Le A 17 393Le A 17 393
8Ο98Οδ/θΊ558Ο98Οδ / θΊ55
©OPV© OPV
2637QQ72637QQ7
ester bzw. -esteramide durch eine hervorragende insektizide Wirksamkeit aus. Sie wirken gegen Pflanzen-, Hygiene- und Vorratsschädlinge und auf dem veterinär-medizinischen Sektor gegen Ektoparasiten. Sie besitzen bei geringer Phytotoxizität sowohl eine gute Wirkung gegen saugende als auch fressende Insekten.esters or ester amides are characterized by their excellent insecticidal effectiveness. They work against plant, hygiene and Storage pests and in the veterinary-medical sector against ectoparasites. They have low phytotoxicity a good effect against sucking as well as eating insects.
Aus diesem Grunde können die erfindungsgemäßen Verbindungen mit Erfolg im Pflanzenschutz sowie auf dem Hygiene-, Vorratsschutz- und Veterinärsektor als Schädlingsbekämpfungsmittel eingesetzt werden.For this reason, the compounds according to the invention can be used successfully as pesticides in crop protection and in the hygiene, stored product protection and veterinary sectors can be used.
Die Wirkstoffe eignen sich bei guter Pflanzenverträglichkeit und gUnstiger WarmblUtertoxizität zur Bekämpfung von tierischen Schädlingen, insbesondere Insekten,The active ingredients are suitable if they are well tolerated by plants and inexpensive warm-blooded toxicity for combating animal Pests, especially insects,
die in der Landwirtschaft, in Forsten, im Vorrats- und Materialschutz sowie auf dem Hygienesektor vorkommen. Sie sind gegen normal sensible und resistente Arten sowie gegen alle oder einzelne Entwicklungsstadien wirksam. Zu den oben erwähnten Schädlingen gehören:those in agriculture, in forests, in the protection of stocks and materials as well as in the hygiene sector. They are against normally sensitive and resistant species as well as against all or individual stages of development effective. The pests mentioned above include:
Aus der Ordnung der Isopoda z. B. Oniscus asellus, Armadillidium vulgäre, Porcellio scaber.From the order of the Isopoda, for. B. Oniscus asellus, Armadillidium vulgare, Porcellio scaber.
Aus der Ordnung der Diplopoda z. B. Blaniulus guttulatus.From the order of the Diplopoda, for. B. Blaniulus guttulatus.
Aue der Ordnung der Chilopoda z. B. Geophllus carpophagus, Scutigera spec. Aue of the order of the Chilopoda z. B. Geophllus carpophagus, Scutigera spec.
Aua der Ordnung der Symphyla z. B. Scutigerella Immaculata.Aua of the order of the Symphyla z. B. Scutigerella Immaculata.
Aus der Ordnung der Thysanura z. B. Lepiema saccharine. From the order of the Thysanura z. B. Lepiema saccharine.
Aue der Ordnung der Collembola z. B. Onychiurus armatus. Aue of the order of the Collembola z. B. Onychiurus armatus.
Aus der Ordnung der Orthoptera z. B. Blatta orientalis, Feriplaneta americana, Leucophaea mader«·, Blattella germanica, Aoheta doaeeticue, Gryllotalpa spp., Locust« migratoria e&gratorioidee, Melanoplus differentialie, Schietocerca From the order of the Orthoptera z. B. Blatta orientalis, Feriplaneta americana, Leucophaea mader ", Blattella germanica, Aoheta doaeeticue, Gryllotalpa spp., Locust" migratoria e & gratorioidee, Melanoplus differentialie, Schietocerca
Lf> » Π 313 - 7 - Lf> »Π 313 - 7 -
809808/0166809808/0166
Aus der Ordnung der Dermaptera z. B. Forficula auricularia. From the order of the Dermaptera, for. B. Forficula auricularia.
Aus der Ordnung der Isoptera z. B. Reticulitermes spp.. From the order of the Isoptera, for. B. Reticulitermes spp ..
Aus der Ordnung der Anoplura z. B. Phylloxera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp,, Linognathus spp.From the order of the Anoplura, e.g. B. Phylloxera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp, Linognathus spp.
Aus der Ordnung der Mallophaga z.B. Trichodectes spp., DamalineaFrom the order of the Mallophaga, e.g. Trichodectes spp., Damalinea
Aus der Ordnung der Thysanoptera z.B. Hercinothrips femoralis, Thrips tabaci. v From the order of the Thysanoptera, for example Hercinothrips femoralis and Thrips tabaci. v
Aus der Ordnung der Heteroptera z.B. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.From the order of the Heteroptera e.g. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.
Aus der Ordnung der Homoptera z.B. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Erio.soma lanigerum, Hyalopterus arundinis, Macrosiphunl avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus,. Nilaparvata lugens, Aonldiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp..Phorodon humuli, Rhopalosiphum brassicae from the order of Homoptera, for example Aleurodes, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii brassicae Brevicoryne, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Erio.soma lanigerum, Hyalopterus arundinis, Macrosiphunl avenae, Myzus spp., Padi , Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Leca nium corni, Saissetia oleae, Laodelphax striatellus ,. Nilaparvata lugens, Aonldiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp ..
blancardella, Hyponomeuta padella, Plutella maculipennis,blancardella, Hyponomeuta padella, Plutella maculipennis,
Laphygma exigua, Marnestra brassicae, Panolia fl«mme·, Laphygma exigua, Marnestra brassicae, Panolia fl «mme ·,
nubilalis, Epheetia kuehniella, Qalleria atllontlla,nubilalis, Epheetia kuehniella, Qalleria atllontlla,
La A 17 393 " . - · - La A 17 393 ". - · -
iQ$«oi/oiiiiQ $ «oi / oiii
-Vv-Vv
copycopy
Rhizopertha dominica, Bruchidius obtectus, Acanthoscelidee obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotaraa decemlineata, Fhaedon cochleariae, Diabrotica spp., Paylliodes chrysocephala, Epilachna varivestia, Atomaria spp., Oryzaephllus surinamensis, Anthonomus spp., Sitophilua spp., Otiorrhynchus aulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogodern» spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Nlptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotea spp., Conoderua spp·, Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica.Rhizopertha dominica, Bruchidius obtectus, Acanthoscelidee obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotaraa decemlineata, Fhaedon cochleariae, Diabrotica spp., Paylliodes chrysocephala, Epilachna varivestia, Atomaria spp., Oryzaephllus surinamensis, Anthonomus spp., Sitophilua spp., Otiorrhynchus aulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogodern »spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Nlptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotea spp., Conoderua spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica.
Aus der Ordnung der Hymenoptera ζ. B. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa app. Aus der Ordnung der Diptera z.B. Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa. From the order of the Hymenoptera ζ. B. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa app. From the order of the Diptera, for example, Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella spp., Phorbia spp., Phorbia spp., Phorbia spp ., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa.
Aus der Ordnung der Siphonaptera z.B. Xenopsylla cheopis, Ceratophyllus spp..From the order of the Siphonaptera e.g. Xenopsylla cheopis, Ceratophyllus spp ..
Aus der Ordnung der Arachnida z.B. Scorpio maurus, Latrodectus mactans.From the order of the Arachnida, e.g. Scorpio maurus, Latrodectus mactans.
Die Anwendung der erfindungsgemäßen Wirkstoffe erfolgt in Form ihrer handelsüblichen Formulierungen und/oder den aus diesen Formulierungen bereiteten Anwendungsformen.The active compounds according to the invention are used in the form of their commercially available formulations and / or from use forms prepared for these formulations.
Der Wirkstoffgehalt der aus den handelsüblichen Formulierungen bereiteten Anwendungsformen kann in weiten Bereichen variieren. Die Wirkstoffkonzentration der Anwendungsformen kann von 0,0000001 bis zu 100 Gew.-# Wirkstoff, vorzugsweise zwischen 0,01 und 10 Gew.-# liegen.The active ingredient content of the use forms prepared from the commercially available formulations can vary within wide limits. The active ingredient concentration of the use forms can be from 0.0000001 to 100 wt .- # active ingredient, preferably between 0.01 and 10 wt. # Are.
Le A 17 393 - 9 - Le A 17 393 - 9 -
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26370Q726370Q7
Die Anwendung geschieht in einer den Anwendungsformen angepaßten üblichen Weise.They are used in a customary manner adapted to the use forms.
Bei der Anwendung gegen Hygiene- und Vorratsschädlinge zeichnen sich die Wirkstoffe durch eine hervorragende Residualwirkung auf Holz und Ton sowie durch eine gute Alkalistabilität auf gekalkten Unterlagen aus.When used against hygiene and stored product pests, the active ingredients are characterized by an excellent residual effect on wood and clay as well as good alkali stability on limed substrates.
Die Wirkstoffe können in die üblichen Formulierungen übergeführt werden, wie Lösungen, Emulsionen, Spritzpulver, Suspensionen, Pulver, Stäubemittel, Schäume, Pasten, lösliche Pulver, Granulate, Aerosole, Suspensions-Emulsionskonzentrate, Saatgutpuder, Wirkstoff-imprägnierte Natur- und synthetische Stoffe, Feinstverkapselungen in polymeren Stoffen und in HUllmassen für Saatgut, ferner in Formulierungen mit Brennsätzen, wie Räucherpatronen, -dosen, -spiralen u.a. sowie ULV-KaIt- und Wannnebe4--Formulierungen. .The active ingredients can be converted into the usual formulations, such as solutions, emulsions, wettable powders, suspensions, Powders, dusts, foams, pastes, soluble powders, granulates, aerosols, suspension emulsion concentrates, seed powders, Active ingredient-impregnated natural and synthetic materials, Finest encapsulation in polymeric materials and in casing compounds for Seeds, also in formulations with burning charges, such as smoking cartridges, cans, coils, etc. as well as ULV-KaIt- and Wannnebe4 formulations. .
Diese Formulierungen werden in bekannter Weise hergestellt, z.3. durch Vermischen der Wirkstoffe mit Streckmitteln, also flüssigen Lösungsmitteln, unter Druck stehenden verflüssigten Gasen und/oder festen Trägerstoffen, gegebenenfalls unter Verwendung von oberflächenaktiven Mitteln, also Emulgiermitteln und/oder Dispergiermitteln und/oder schaumerzeugenden Mitteln, Im Falle der Benutzung von Wasser als Streckmittel können z.B. ' auch organische Lösungsmittel als Hilfslösungsmittel verwendet werden. Als flüssige Lösungsmittel kommen im wesentlichen infrage: Aromaten, wie Xylol, Toluol, oder Alky!naphthaline, chlorierte Aromaten oder chlorierte aliphatische Kohlenwasserstoffe, wie Chlorbenzole, Chloräthylene oder Methylenchlorid, . aliphatische Kohlenwasserstoffe, wie Cyclohexan oder Paraffine, z.B. Erdölfraktionen, Alkohole, wie Butanol oder GlycolThese formulations are prepared in a known manner, e.g. by mixing the active ingredients with extenders, that is liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using of surface-active agents, i.e. emulsifiers and / or dispersants and / or foam-generating agents, If water is used as an extender, organic solvents, for example, can also be used as auxiliary solvents will. The main liquid solvents that can be used are: Aromatics such as xylene, toluene, or alkyl naphthalenes, chlorinated Aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride. aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. petroleum fractions, alcohols such as butanol or glycol
Le A 17 393 - 10 - Le A 17 393 - 10 -
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/ . 73 263 7QQ 7-/. 73 263 7QQ 7-
sowie deren Äther und Ester, Ketone, wie Aceton, Methyläthy!keton, Methylisobutylketon oder Cyclohexanon, stark polare Lösungsmittel, wie Dimethylformamid und Dimethylsulfoxid, sowie Wasser; mit verflüssigten gasförmigen Streckmitteln oder Trägerstoff.en sind solche Flüssigkeiten gemeint, welche bei normaler Temperatur und unter Normaldruck gasförmig sind, z.B. Aerosol-Treibgase, wie Halogenkohlenwas-( serstoffe sowie Butan, Propan, Stickstoff und Kohlendioxid; als feste Trägerstoffe: natürliche Gesteinsmehle, wie Kaoline, Tonerden," Talkum, Kreide, Quarz, Attapulgit, Montmorillonit oder Diatomeenerde und synthetische Gesteinsmehle, wie hochdisperse Kieselsäure, Aluminiumoxid und Silikate; als feste Trägerstoffe für Granulate: gebrochene und fraktionierte natürliche Gesteine wie Calcit, Marmor, Bims, Sepiolith, Dolomit sowie synthetische Granulate aus anorganischen und organischen Mehlen sowie Granulate aus organischem Material wie Sägemehle, Kokosnußschalen, Maiskolben und Tabakstengel; als Emulgier- und/oder schaumerzeugende Mittel: nichtionogene und anionische Emulgatoren, wie Polyoxyäthylen-Fettsäure-Ester, Polyoxyäthylen-Fettalkohol-Äther, z.B. Alkylaryl-polyglykol-äther, Alkylsulfonate, Alkylsulfate, Arylsulfonate sowie Eiwelßhydrolysate; als Dispergiermittel: z.B. Lignin, Sulfitablaugen und Methylcellulose. and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water; by liquefied gaseous extenders or Trägerstoff.en are meant liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as Halogenkohlenwas- (bons as well as butane, propane, nitrogen and carbon dioxide; as solid carriers, ground natural minerals, such as Kaolins, clays, "talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock flour, such as finely divided silica, aluminum oxide and silicates; as solid carriers for granulates: broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well synthetic granules made from inorganic and organic flours and granules made from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; as emulsifiers and / or foam-producing agents: nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. alkylaryl -polyglycol ether , Alkylsulphonates, alkylsulphates, arylsulphonates and protein hydrolysates; as dispersants: e.g. lignin, sulphite waste liquors and methyl cellulose.
Es können in den Formulierungen Haftmittel wie Carboxymethylcellulose, natürliche und synthetische pulverige, körnige oder latexförmige Polymere verwendet werden, wie Gummiarabicum, Polyvinylalkohol, Polyvinylacetat, Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices , such as gum arabic, polyvinyl alcohol, polyvinyl acetate, can be used in the formulations,
Es können Farbstoffe wie anorganische Pigmente, z.B. Eisen oxid, Titanoxid, Ferrocyanblau und organische Farbstoffe, Dyes such as inorganic pigments, e.g. iron oxide, titanium oxide, ferrocyan blue and organic dyes,
Le A 17 393 - 11 - Le A 17 393 - 11 -
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copycopy
1lf 26370Q7 1lf 26370Q7
wie Alizarin-, Azo-Metallphthalocyaninfarbstoffe und Spurennährstoffe wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink verwendet werden.such as alizarin, azo-metal phthalocyanine dyes, and Trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
Die Formulierungen enthalten im allgemeinen zwischen 0,1 und 95 Gewichtsprozent Wirkstoff, vorzugsweise zwischen 0,5 und 90 %. The formulations generally contain between 0.1 and 95 percent by weight of active ingredient, preferably between 0.5 and 90 %.
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LT100-TeSt für Dipteren
Testtiere: Aedes aepypti
Lösungsmittel: AcetonLT 100 -Test for Diptera
Test animals: Aedes aepypti
Solvent: acetone
2 Gewichtsteile Wirkstoff werden in 1 000 Volumenteilen Lösungsmittel aufgenommen. Die so erhaltene Lösung wird mit weiterem Lösungsmittel auf die gewünschten geringeren Konzentrationen verdünnt.2 parts by weight of active ingredient are dissolved in 1,000 parts by volume of solvent recorded. The solution obtained in this way is adjusted to the desired lower concentrations with further solvent diluted.
2,5 ml Wirkstofflösung werden in eine Petrischale pipettiert. Auf dem Boden der Petrischale befindet sich ein Filterpapier mit einem Durchmesser von etwa 9,5 cm. Die Petrischale bleibt so lange offen stehen, bis das Lösungsmittel vollständig verdunstet ist. Je nach Konzentration der Wirkstofflösung ist die Menge Wirkstoff pro m Filterpapier verschieden hoch. Anschließend gibt man etwa 25 Testtiere in die Petrischale und bedeckt sie mit einem Glasdeckel.2.5 ml of the active ingredient solution are pipetted into a Petri dish. A filter paper with a diameter of about 9.5 cm is located on the bottom of the Petri dish. The petri dish remains Stand open until the solvent has completely evaporated. Depending on the concentration of the active ingredient solution the amount of active ingredient per m of filter paper varies. Then about 25 test animals are placed in the Petri dish and covers them with a glass lid.
Der Zustand der Testtiere wird laufend kontrolliert. Es wird diejenige Zeit ermittelt, welche für eine 100 96ige Abtötung notwendig ist.The condition of the test animals is continuously monitored. It is determined that the time which is necessary for a 100 96ige killing.
Testtiere, Wirkstoffe, Wirkstoffkonzentrationen und Zeiten, bei denen eine 100 #ige Abtötung vorliegt, gehen aus der nach folgenden Tabelle 1 hervor: Test animals, active ingredients, active ingredient concentrations and times at which there is 100 % destruction are shown in Table 1 below:
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Tabelle 1Table 1
für Dipteren / Aedes aepypti)for Diptera / Aedes aepypti)
Wirkstoff Wirkstoffkonzentration der
Losung in %Active ingredient active ingredient concentration of the
Solution in%
inin
Minuten ( )Minutes ()
,0 f, , 0 f,
CH.CH.
f^-O-P- (OC2H5)f ^ -OP- (OC 2 H 5 )
(bekannt) 0,2(known) 0.2
120'120 '
0^-0-P-(OCH3)0 ^ -0-P- (OCH 3 )
tert.-C4H9 0,2tert-C 4 H 9 0.2
60"60 "
tert.-C4H9 tert-C 4 H 9
0-0-P- (OC2H5) 0,20-0-P- (OC 2 H 5 ) 0.2
60"60 "
tert.-Ctert-C
-0-P,-0-P,
4H9 0,2 4 H 9 0.2
60'60 '
tert.-tert.-
S -0-PS -0-P
^OC3H7-n 0,2^ OC 3 H 7 -n 0.2
60'60 '
tert.-C4H9 tert-C 4 H 9
0,20.2
60'60 '
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2637QQ72637QQ7
Tabelle 1 (Fortsetzung) Table 1 (continued)
für Dipteren /Aedes aepypti)for Diptera / Aedes aepypti)
Wirkstoff Wirkstoffkonzen- LTioo in tration der Minuten C) Losung in %Active ingredient active ingredient concentration LT ioo in tration of minutes C) solution in%
tert.-C4H9 0,2 tert-C 4 H 9 0.2
60'60 '
„ 0C-.H_-iso 7 "0C-.H_-iso 7
tert.-CfjHg 0,2 tert-CfjHg 0.2
60'60 '
S OC5H1. .0 „/ 2S OC 5 H 1 . .0 "/ 2
)-P ^SC3H7-I1 ) -P ^ SC 3 H 7 -I 1
tert.-C4H9 0,2 tert-C 4 H 9 0.2
60'60 '
NH-C3H7-isoNH-C 3 H 7 -iso
tert.-C4H9 tert-C 4 H 9
3H7-0,2 3 H 7 - 0.2
60! 60 !
0,20.2
60'60 '
tert-C4H9 tert -C 4 H 9
NH-C3H7-XSO 0,2 NH-C 3 H 7 -XSO 0.2
60"60 "
Le A 17 - 15 - Le A 17 - 15 -
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2637Q07 •7* 2637Q07 • 7 *
BeispielB
Mückenlarven-Test Example B.
Mosquito larva test
Testtiere: Aedes aepypti-LarvenTest animals: Aedes aepypti larvae
Lösungsmittel: 99 Gewichtsteile AcetonSolvent: 99 parts by weight acetone
Emulgator: 1 Gewichtsteil Benzylhydroxidiphenylpolygly-Emulsifier: 1 part by weight of Benzylhydroxidiphenylpolygly-
kolätherKoläther
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung löst man 2 Gewichtsteile Wirkstoff in 1000 Volumenteilen Lösungsmittel, das Emulgator in der oben angegebenen Menge enthält. Die so erhaltene Lösung wird mit Wasser auf die gewünschten geringeren Konzentrationen verdünnt.To produce an appropriate preparation of active ingredient, 2 parts by weight of active ingredient are dissolved in 1000 parts by volume Solvent containing the emulsifier in the amount specified above. The solution thus obtained is mixed with water diluted to the desired lower concentrations.
Man füllt die wässrigen Wirkstoffzubereitungen in Gläser und setzt anschließend etwa 25 Mückenlarven in jedes Glas ein.The aqueous active ingredient preparations are filled into glasses and about 25 mosquito larvae are then placed in each glass a.
Nach 24 Stunden wird die Abtötung in % bestimmt. Dabei bedeutet 100 %, daß alle Larven abgetötet wurden; 0 % bedeutet, daß keine Larven abgetötet wurden.The destruction in% is determined after 24 hours. 100% means that all larvae have been killed; 0 % means that none of the larvae have been killed.
Wirkstoffe, Wirkstoffkonzentrationen, Testtiere und Resultate gehen aus der nachfolgenden Tabelle 2 hervor:Active ingredients, active ingredient concentrations, test animals and The results are shown in Table 2 below:
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Tabelle 2Table 2
(Mückenlarven-Test / Aedes aepypti-Larven)(Mosquito larva test / Aedes aepypti larvae)
WirkstoffActive ingredient
Wirkstoffkon- Abtötungszentration der grad in % Lösung in ppmActive ingredient concentration concentration of the degree in% solution in ppm
0,10.1
(bekannt)(known)
tert.-C4H9 tert-C 4 H 9
0,10.1
100100
-0-P.-0-P.
tert.-C4H9 tert-C 4 H 9
0,10.1
9090
tert.-C4H9 tert-C 4 H 9
tert.tert.
Λ _ »/°C2H5 3H7" Λ _ »/ ° C 2 H 5 3 H 7"
CH.CH.
sOC3H7-n s OC 3 H 7 -n
0,10.1
0,10.1
100100
100100
tert.-Ctert-C
-0-P(OC2H5) 0,1-0-P (OC 2 H 5 ) 0.1
100100
Le A 17 393Le A 17 393
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Ζ»Ζ »
Tabelle 2 (Fortsetzimg) Table 2 (continued)
(Mickenlarven-Test / Aedes aepypti-Larven)(Mickenlarven-Test / Aedes aepypti-Larvae)
Wirkstoff Wirkstoffkon- AbtötungsgradActive ingredient active ingredient killing degree
zentration der grad in % Lösung in ppmconcentration of the degree in% solution in ppm
P (CCT )P (CCT)
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Beispiel c
Phaedon-Larven-Test Example c
Phaedon larvae test
Lösungsmittel: 3 Gewichtsteile Aceton Emulgator: 1 Gewichtsteil AlkylarylpolyglykolätherSolvent: 3 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit der angegebenen Menge Lösungsmittel und der angegebenen Menge Emulgator und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration. To produce an appropriate preparation of active ingredient, 1 part by weight of active ingredient is mixed with the specified Amount of solvent and the specified amount of emulsifier and dilute the concentrate with water to the desired concentration.
Mit der Wirkstoffzubereitung besprüht man Kohlblätter (Brassica oleracea) tropfnaß und besetzt sie mit Meerrettichblattkäfer-Larven (Phaedon Cochleariae).Cabbage leaves (Brassica oleracea) are sprayed to runoff with the preparation of active compound and are populated with mustard beetle larvae (Phaedon Cochleariae).
Nach den angegebenen Zeiten wird die Abtötung in % bestimmt. Dabei bedeutet 100 %, daß alle Käfer-Larven abgetötet wurden; 0 % bedeutet, daß keine Käfer-Larven abgetötet wurden.After the specified times, the destruction is determined in % . 100 % means that all beetle larvae have been killed; 0 % means that none of the beetle larvae have been killed.
Wirkstoffe, Wirkstoffkonzentrationen, Zeiten der Auswertung und Resultate gehen aus der nachfolgenden Tabelle 3 hervor:Active ingredients, active ingredient concentrations, times of evaluation and results are shown in Table 3 below:
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Tabelle 3Table 3
(Phaedon-Larven-Te st)(Phaedon larvae te st)
WirkstoffActive ingredient
Wirkstoffkonzentration in % AbtötungsgradActive ingredient concentration in% degree of destruction
in % nach 3 Tagenin% after 3 days
CH,CH,
(bekannt)(known)
Il IIl I
(CH3O) 2P-O-k ^ N(CH 3 O) 2 POk ^ N
C4H9-tert.C 4 H 9 tert.
0,1 0,010.1 0.01
0,1 0,01 100 00.1 0.01 100 0
100 100100 100
C4H9-tert.C 4 H 9 tert.
C4H9-tert.C 4 H 9 tert.
0,1 0,010.1 0.01
0,1 0,01 100 1000.1 0.01 100 100
100 100100 100
C2H5°\».nJ C 2 H 5 ° ". n y
.C4H9-tert.C 4 H 9 tert
0,1 0f01 100 1000.1 0 f 01 100 100
4H9-tert. 4 H 9 tert.
0,1 0,01 1OO 1000.1 0.01 100 100
Le A 17 393Le A 17 393
- 20 -- 20 -
809808/0155809808/0155
Tabelle 3 (Phaedon-Larven-Test) Table 3 (Phaedon larvae test)
(Fortsetzung)(Continuation)
zentration in %Active ingredient con
centering in%
0,010.1
0.01
in % nach 3 TagenDegree of destruction
in% after 3 days
ISO-C3H7O „
3ο
ISO-C 3 H 7 O "
3
IlS.
Il
0,010.1
0.01
100100
100
IsO-C3H7-NH C 2 H 5 ° ~ ^
IsO-C 3 H 7 -NH
Il0
Il
100100
100
Le A 17 393Le A 17 393
- 21 -- 21 -
109808/0155109808/0155
Herstellungsbeispiele ^ Production examples ^
Beispiel 1; tert.-CrH, Example 1; tert-CrH,
Zu einer Mischung von 14,1 g (o,l Mol) >tert.-Butyl-4-hydroxyisoxazol in 2oo ml Acetonitril und 14,5 g (o,lo5 Mol) Kaliumcarbonat werden bei 2o°C 18,8 g (o,l Mol) Ο,Ο-Diäthylthionophosphorsäurediesterchlorid getropft. Man erwärmt den Ansatz 3 Std. auf 5O°C, kühlt ihn dann ab und gießt das Reaktionsgemisch in 300 ml Toluol. Die Toluollösung wird mit gesättigter Natriumbicarbonatlösung und Wasser gewaschen, über Natriumsulfat getrocknet und dann eingeengt. Nach dem Andestillieren erhält man 2o g (68?έ der Theorie) 0,0-Diäthyl-0-[j5-tert.-butyl-isoxazol(5)y3-thionophosphorsäureester in Form eines braunen Öls mit dem Brechungsindex n^6:1,4695.18.8 g (o , l mol) Ο, Ο-diethylthionophosphoric acid diester chloride dripped. The batch is heated to 50 ° C. for 3 hours, then cooled and the reaction mixture is poured into 300 ml of toluene. The toluene solution is washed with saturated sodium bicarbonate solution and water, dried over sodium sulfate and then concentrated. After partial distillation, 20 g (68% of theory) of 0,0-diethyl-0- [j5-tert-butyl-isoxazole (5) y3- th ionophosphoric acid ester are obtained in the form of a brown oil with the refractive index n ^ 6 : 1.4695.
In analoger Weise können die folgenden Verbindungen der FormelThe following compounds of the formula
AAAA
η /ORη / OR
o-p( 2 op ( 2
R^R ^
(D(D
hergestellt werden:getting produced:
Bei- Ausbeute Brechungsspiel i 5 ( % der index: At- yield refraction clearance i 5 ( % of the index:
Nr. R R1 R^ X Theorie)No.RR 1 R ^ X theory)
2 H C2H5 SC3H7-n S 62 n^8:l,5oll2 HC 2 H 5 SC 3 H 7 -n S 62 n ^ 8 : 1.5 inch
3 H C2H5 OC2H5 0 48 n|8:l,442o3 HC 2 H 5 OC 2 H 5 0 48 n | 8 : 1,442o
Le A 17 393 - 22 -Le A 17 393 - 22 -
809808/0155809808/0155
2637QQ72637QQ7
spiel
Nr. Rat
game
No. R
(% der Brechungs-
Theorie ) index:yield
(% of refractive
Theory) index:
109808/0155109808/0155
I JI J
Die als Ausgangsmaterialien benötigten 3-tert.-Butyl-5-hyd.roxyisoxazolderivate (II) können z.B. wie im folgenden beschrieben hergestellt werden:The 3-tert-butyl-5-hydroxyisoxazole derivatives required as starting materials (II) can be produced e.g. as described below:
^OH RIB 4956^ OH RIB 4956
Zu einer Lösung von 108 g (2 Mol) Natriummethylat in 4oo ml Methanol werden unter Eiskühlung portionsweise 69,5 g (1 Mol) Hydroxylammoniumchlorid gefügt. Dann tropft man 172 g (1 Mol) Pivaloylessigsäureäthylester der Mischung zu und erwärmt sie 6 Std. auf 60 C. Anschließend wird die Reaktionslösung eingeengt und der Rückstand mit 200 ml Wasser aufgenommen. Nach Zugabe von konzentrierter Salzsäure bis pH y6 entsteht ein farbloser Niederschlag, der abgesaugt und getrocknet wird. Man erhält 120 g (85 % der Theorie) S-tert.-Butyl-S-hydroxy— isoxazol in Form farbloser Kristalle vom Schmelzpunkt 110°C.69.5 g (1 mol) of hydroxylammonium chloride are added in portions to a solution of 108 g (2 mol) of sodium methylate in 400 ml of methanol while cooling with ice. 172 g (1 mol) of ethyl pivaloylacetate are then added dropwise to the mixture and heated to 60 ° C. for 6 hours. The reaction solution is then concentrated and the residue is taken up in 200 ml of water. After adding concentrated hydrochloric acid to pH y 6, a colorless precipitate is formed, which is filtered off with suction and dried. 120 g (85% of theory) of S-tert-butyl-S-hydroxy-isoxazole are obtained in the form of colorless crystals with a melting point of 110.degree.
In analoger Weise können die folgenden Verbindungen der FormelThe following compounds of the formula
I T (II)I T (II)
hergestellt werden:getting produced:
Ausbeuteyield
R . Physikal.Daten ^
CH^S teilkristallin 33 R. Physical.Data ^
CH ^ S partially crystalline 33
Le A 17 393 - 24 - Le A 17 393 - 24 -
iBSlOl/illliBSlOl / illl
Claims (6)
R , R und X die in Anspruch 1 angegebene Bedeutung1 2
R, R and X have the meaning given in claim 1
Hai für Halogen, vorzugsweise Chlor, steht,have and
Hai represents halogen, preferably chlorine,
Priority Applications (13)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19762637007 DE2637007A1 (en) | 1976-08-17 | 1976-08-17 | ISOXAZOLYL (THIONO) (THIOL) -PHOSPHOR (PHOSPHON) -SAEESESTERS OR. -ESTERAMIDES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS INSECTICIDES |
PT66913A PT66913B (en) | 1976-08-17 | 1977-08-12 | ISOXAZOLYL (THIONO) (THIOL) PHOSPHORIC ACID ESTERS AND ESTERAMIDES PROCESS FOR THEIR PREPARATION AND THEIR USE AS INSECTICIDES |
IL52735A IL52735A0 (en) | 1976-08-17 | 1977-08-15 | Novel esters and ester-amides of phosphoric and phosphonic acids and of their mono- and dithio-analogues their preparation and their use as insecticides |
JP9709377A JPS5323968A (en) | 1976-08-17 | 1977-08-15 | Novel isoxazolyl*thiono**thiol**phosphate *phosphonate* esters and esterramides and its use as insecticide |
FR7725045A FR2362153A1 (en) | 1976-08-17 | 1977-08-16 | O-Tert. butyl-isoxazolyl (thio)phosph(on)ate and corresp. amide cpds. - useful as insecticides with low toxicity for plants and mammals |
SE7709226A SE7709226L (en) | 1976-08-17 | 1977-08-16 | ISOXAZOLYL (TIONO) (TIOL) - PHOSPHORUS (PHOSPHON) - ACID ESTERS AND ESTERAMIDES USED AS INSECTICIDES AND METHODS OF PREPARING THE COMPOUNDS |
ZA00774940A ZA774940B (en) | 1976-08-17 | 1977-08-16 | Novel isoxazolyl(thiono)(thiol)-phosphoric(phosphonic)acid esters and esteramides and their use as insecticides |
ES461622A ES461622A1 (en) | 1976-08-17 | 1977-08-16 | Novel isoxazolyl*thiono**thiol**phosphate *phosphonate* esters and esterramides and its use as insecticide |
BR7705411A BR7705411A (en) | 1976-08-17 | 1977-08-16 | PROCESS FOR THE PREPARATION OF ESTERS OR STERAMIDES OF ISOXAZOLIL (TIONO) (TIOL) -Phosphoric (Phosphonic) Acids and Insecticide-Based Compounds |
DK364377A DK364377A (en) | 1976-08-17 | 1977-08-16 | ISOXAXOLYL- (THIONO) (THIOL) -PHOSPHOR (PHOSPHON)-ACID RESIDERS OR ESTERAMIDS PROCEDURE FOR THEIR PREPARATION AND USE AS INSECTICIDES |
NL7709038A NL7709038A (en) | 1976-08-17 | 1977-08-16 | ISOXAZOLYL (THIONO) (THIOL) -PHOSPHORUS (PHOSPHON) ACID ESTERS RESPECTIVELY ESTAMAMIDS, METHOD FOR PREPARING IT AND ITS USE AS INSECTICIDE. |
PL20029977A PL200299A1 (en) | 1976-08-17 | 1977-08-16 | INSECTOR AND METHOD OF ESTRAS PRODUCTION RELATIVE TO ESTRES OF ESTRES OF ISOXAZOLYLOSIC (THIONO / THIOLO) -PHOSPHORIC (PHOSPHONIC) ACIDS |
BE180226A BE857855A (en) | 1976-08-17 | 1977-08-17 | NEW ESTERS AND AMIDES OF ISOXAZOLYL ACID (THIONO) (THIOL) -PHOSPHORIC (PHOSPHONIC) ESTERS, THEIR METHOD OF PREPARATION AND APPLICATION |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19762637007 DE2637007A1 (en) | 1976-08-17 | 1976-08-17 | ISOXAZOLYL (THIONO) (THIOL) -PHOSPHOR (PHOSPHON) -SAEESESTERS OR. -ESTERAMIDES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS INSECTICIDES |
Publications (1)
Publication Number | Publication Date |
---|---|
DE2637007A1 true DE2637007A1 (en) | 1978-02-23 |
Family
ID=5985652
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19762637007 Pending DE2637007A1 (en) | 1976-08-17 | 1976-08-17 | ISOXAZOLYL (THIONO) (THIOL) -PHOSPHOR (PHOSPHON) -SAEESESTERS OR. -ESTERAMIDES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS INSECTICIDES |
Country Status (13)
Country | Link |
---|---|
JP (1) | JPS5323968A (en) |
BE (1) | BE857855A (en) |
BR (1) | BR7705411A (en) |
DE (1) | DE2637007A1 (en) |
DK (1) | DK364377A (en) |
ES (1) | ES461622A1 (en) |
FR (1) | FR2362153A1 (en) |
IL (1) | IL52735A0 (en) |
NL (1) | NL7709038A (en) |
PL (1) | PL200299A1 (en) |
PT (1) | PT66913B (en) |
SE (1) | SE7709226L (en) |
ZA (1) | ZA774940B (en) |
-
1976
- 1976-08-17 DE DE19762637007 patent/DE2637007A1/en active Pending
-
1977
- 1977-08-12 PT PT66913A patent/PT66913B/en unknown
- 1977-08-15 IL IL52735A patent/IL52735A0/en unknown
- 1977-08-15 JP JP9709377A patent/JPS5323968A/en active Pending
- 1977-08-16 ZA ZA00774940A patent/ZA774940B/en unknown
- 1977-08-16 ES ES461622A patent/ES461622A1/en not_active Expired
- 1977-08-16 NL NL7709038A patent/NL7709038A/en not_active Application Discontinuation
- 1977-08-16 SE SE7709226A patent/SE7709226L/en unknown
- 1977-08-16 FR FR7725045A patent/FR2362153A1/en not_active Withdrawn
- 1977-08-16 BR BR7705411A patent/BR7705411A/en unknown
- 1977-08-16 DK DK364377A patent/DK364377A/en unknown
- 1977-08-16 PL PL20029977A patent/PL200299A1/en unknown
- 1977-08-17 BE BE180226A patent/BE857855A/en unknown
Also Published As
Publication number | Publication date |
---|---|
ES461622A1 (en) | 1978-06-16 |
SE7709226L (en) | 1978-02-18 |
JPS5323968A (en) | 1978-03-06 |
IL52735A0 (en) | 1977-10-31 |
BR7705411A (en) | 1978-05-16 |
NL7709038A (en) | 1978-02-21 |
DK364377A (en) | 1978-02-18 |
BE857855A (en) | 1978-02-17 |
PL200299A1 (en) | 1978-04-10 |
PT66913A (en) | 1977-09-01 |
ZA774940B (en) | 1978-06-28 |
FR2362153A1 (en) | 1978-03-17 |
PT66913B (en) | 1979-02-02 |
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