DE2419623A1 - 0-TRIAZOLYL- (THIONO) -PHOSPHORUS (PHOSPHONE) ACID ESTER OR. -ESTERAMIDE, THE PROCESS FOR THEIR MANUFACTURING AND THEIR USE AS INSECTICIDE, ACARICIDE AND NEMATICIDE - Google Patents
0-TRIAZOLYL- (THIONO) -PHOSPHORUS (PHOSPHONE) ACID ESTER OR. -ESTERAMIDE, THE PROCESS FOR THEIR MANUFACTURING AND THEIR USE AS INSECTICIDE, ACARICIDE AND NEMATICIDEInfo
- Publication number
- DE2419623A1 DE2419623A1 DE2419623A DE2419623A DE2419623A1 DE 2419623 A1 DE2419623 A1 DE 2419623A1 DE 2419623 A DE2419623 A DE 2419623A DE 2419623 A DE2419623 A DE 2419623A DE 2419623 A1 DE2419623 A1 DE 2419623A1
- Authority
- DE
- Germany
- Prior art keywords
- thiono
- phosphorus
- lea
- triazolyl
- formula
- 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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- MVEKXQBZICSLMC-UHFFFAOYSA-N butan-2-yl ethoxy hydrogen phosphate Chemical compound C(C)OOP(OC(C)CC)(O)=O MVEKXQBZICSLMC-UHFFFAOYSA-N 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 208000031513 cyst Diseases 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 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
- 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
- 239000003085 diluting agent Substances 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- YYJNOYZRYGDPNH-MFKUBSTISA-N fenpyroximate Chemical compound C=1C=C(C(=O)OC(C)(C)C)C=CC=1CO/N=C/C=1C(C)=NN(C)C=1OC1=CC=CC=C1 YYJNOYZRYGDPNH-MFKUBSTISA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 235000020044 madeira Nutrition 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 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
- 238000002156 mixing Methods 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil 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
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000003531 protein hydrolysate 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
- 230000035484 reaction time Effects 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
- 241000894007 species Species 0.000 description 1
- 238000005507 spraying 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
- 239000011593 sulfur Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003580 thiophosphoric acid esters Chemical class 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
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
- C07F9/6515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having three nitrogen atoms as the only ring hetero atoms
- C07F9/6518—Five-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
Zentralbereich Patente, Marken und LizenzenCentral area of patents, trademarks and licenses
509 Leverkusen, Bayerwerk509 Leverkusen, Bayerwerk
Hu/Zl IaHu / Zl Ia
0-Triazolyl-(thiono)-phosphor(phosphon)-säureester bzw. -esteramide, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Insektizide, Akarizide und Nematizide0-triazolyl (thiono) phosphorus (phosphonic) acid esters or ester amides, Process for their production and their use as insecticides, acaricides and nematicides
Die vorliegende Erfindung betrifft neue O-Triazolyl-(thiono)-phosphor(phosphon)-säureester bzw. -esteramide, ein Verfahren zu ihrer Herstellung sowie ihre Verwendung als Insektizide, Akarizide und Nematozide.·The present invention relates to new O-triazolyl (thiono) phosphorus (phosphonic) acid esters or esteramides, a process for their production and their use as insecticides, Acaricides and nematocides.
Es ist bereits bekannt, daß 0,0-Dimethyl-O-/3-methylpyrazol(5) y 17-und 0,0-Diäthyl-0-/l-isopropyl-5-methylmercapto-(i ,2,4)-triazol(3)yl_7-thiono-phosphorsäureester insektizide und akarizide Eigenschaften besitzen (vgl. die US-PS 2 754 244 und die DT-OS 2 259 960).It is already known that 0,0-dimethyl-O- / 3-methylpyrazole (5) y 17- and 0,0-diethyl-0- / 1-isopropyl-5-methylmercapto- (i, 2,4) -triazol (3) yl-7-thionophosphoric acid ester Have insecticidal and acaricidal properties (cf. US Pat. No. 2,754,244 and US Pat DT-OS 2 259 960).
Es wurde gefunden, daß die neuen O-Triazolyl-(thiono)-phosphor-(phosphon)-säureester-bzw.-esteramide der FormelIt has been found that the new O-triazolyl (thiono) phosphorus (phosphonic) acid esters or ester amides the formula
in welcherin which
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κ*κ *
R Alkyl mit 1 "bis 6,R alkyl with 1 "to 6,
R' Alkyl, Alkylamino oder Alkoxy mit. jeweils 1 bis 6R 'is alkyl, alkylamino or alkoxy with. 1 to 6 each
Kohlenstoffatomen oder Phenyl/ R!' Alkenyl mit 1 bis 6 Kohlenstoffatomen und X ein Sauerstoff- oder Schwefelatom bedeuten,Carbon atoms or phenyl / R ! 'Alkenyl with 1 to 6 carbon atoms and X is an oxygen or sulfur atom,
starke insektizide, akarizide und nematizide Eigenschaften besitzen.strong insecticidal, acaricidal and nematicidal properties own.
Weiterhin wurde gefunden,» daß die neuen O-Triazolyl-(thiono)-phosphor(phosphon)-säureester bzw. -esteramide der Konstitution (i) erhalten werden, wenn man (Thiono)Phosphor(phosphon) säureester- bzw. -esteraißidhalogenide der FormelIt was also found that »the new O-triazolyl (thiono) phosphorus (phosphonic) acid esters or ester amides of constitution (i) are obtained if (thiono) phosphorus (phosphon) acid ester or ester aiside halides of the formula
in welcherin which
/ P-HaI/ P-HaI
X, R und R' die oben angegebene Bedeutung besitzen und Hai ein Halogen-, vorzugsweise Chloratom bedeutet,X, R and R 'have the meaning given above and Hal is a halogen, preferably chlorine atom,
mit 1-Phenyl-3-hydroxy-5-alkenylmercapto-triazolderivaten der Formelwith 1-phenyl-3-hydroxy-5-alkenylmercapto-triazole derivatives of formula
in welcherin which
R1' die oben angegebene Bedeutung besitzt,R 1 'has the meaning given above,
in Gegenwart von Säureakzeptoren oder in Form der entsprechenden Alkali-, Erdalkali- oder Ammoniumsalze umsetzt.in the presence of acid acceptors or in the form of the corresponding alkali, alkaline earth or ammonium salts.
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Ãœberraschenderweise besitzen die erfindungsgemäßen O-Triazo-IyI-(thiono)-phosphor(phosphorsäureester bzw. -esteramide eine bessere insektizide, auch bodeninsektizide, akarizide und nematizide Wirkung als vorbekannte Verbhdungen analoger Konstitution und gleicher Wirkungsrichtung. Sie wirken dabei nicht nur gegen pflanzenschädigende Insekten und Milben, sondern auch gegen Hygiene- und Vorratsschädlinge sowie auf dem veterinär-medizinischen Sektor gegen Ektoparasiten, z.B. parasitierende Fliegenlarven. Die erfindungsgemäßen Stoffe stellen somit eine echte Bereicherung der Technik dar. â– Surprisingly, the O-triazo-IyI- (thiono) -phosphorus (phosphoric acid esters) according to the invention or esteramides have a better insecticidal, also soil insecticidal, acaricidal and nematicidal effect than previously known compounds Constitution and the same direction of action. They not only work against plant-damaging insects and mites, but also also against hygiene and storage pests and in the veterinary-medical sector against ectoparasites, e.g. parasitic fly larvae. The substances according to the invention thus represent a real asset to technology. â–
Verwendet man beispielsweise 0,0-Dimethylthionophosphorsäurediesterchlorid und 1-Phenyl-3-hydroxy-5-allylmercapto—triazol.(1,2,4) als Ausgangsmaterialien, so kann der Reaktionsverlauf durch das folgende Formelschema wiedergegeben werden: If, for example, 0,0-dimethylthionophosphoric acid diester chloride and 1-phenyl-3-hydroxy-5-allylmercapto-triazole (1,2,4) are used as starting materials, the course of the reaction can be represented by the following equation:
SCH2-CH=CH2 s SCH2-CH=CHSCH 2 -CH = CH 2 s SCH 2 -CH = CH
mittel u V-/medium u V- /
- KCl - KCl
Die zu verwendenden Ausgangsstoffe sind durch die Formeln (II) und (III) eindeutig allgemein definiert. Vorzugsweise stehen darin jedochThe starting materials to be used are clearly and generally defined by the formulas (II) and (III). Preferably are in it, however
R für geradkettiges oder verzweigtes Alkyl mit 1 bis 5, insbesondere 1 bis 4,R for straight-chain or branched alkyl with 1 to 5, especially 1 to 4,
R1 *r geradkettiges oder verzweigtes Alkyl, Alkoxy oder Monoalkylamino mit jeweils 1 bis 5, insbesondere 1 bis 4 Kohlenstoffatomen oder für PhenylR 1 * r straight-chain or branched alkyl, alkoxy or monoalkylamino each with 1 to 5, in particular 1 to 4 carbon atoms or for phenyl
R1' für Alkenyl mit 1 bis 5 insbesondere 1 bis 4 Kohlenstoffatomen , undR 1 'for alkenyl having 1 to 5, in particular 1 to 4 carbon atoms, and
X für SchwefelX for sulfur
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Die als Ausgangsstoffe zu verwendenden (Thiono)Phosphor(phosphon)-säureester- bzw.-esteramidhalogenide (II) sind aus der Literatur bekannt und können nach üblichen Verfahren - auch großtechnisch - hergestellt werden.The (thiono) phosphorus (phosphonic) acid ester to be used as starting materials or ester amide halides (II) are known from the literature and can - also large-scale - to be produced.
Als Beispiele seien im einzelnen genannt:Examples are:
0,0-Dimethyl-, 0,O-Diäthyl-, 0,0-Di-n-propyl-, 0,0-Di-isopropyl-, 0,0-Di-n-butyl-, 0,0-Di-iso-butyl-, O,O-Di-tert.-butyl-, O-Äthyl-0-n-propyl-, O-Äthyl-0-iso-propyl-, O-Äthyl-O-sec.-butyl-phosphorsäureesterchlorid, sowie O-Methyl-, O-Äthyl-, O-n-Propyl-, O-iso-Propyl-, O-n-Butyl-, O-sec.-Butyl, O-iso-Butyl- oder O-tert.-Butylmethan- bzw. -äthan-, -n-propan-, -iso-propan-, -n-butan-, -iso-butan-, -see.-butan-, -tert.- butan- oder -phenyl-phosphonsäureesterchlorid, ferner O-Methyl-N-methyl-, O-Methyl-N-äthyl-, 0-Methyl-N-n-propyl-, O-Methyl-N-iso-propyl-, O-Methyl-N-n-butyl-, O-Äthyl-N-methyl-, O-Äthyl-N-äthyl-, O-Äthyl-N-n-propyl, 0-Äthyl-N-iso-propyl-, O-Äthyl-N-n-butyl-, O-Äthyl-N-secbutyl-, O-n-Propyl-N-methyl-, O-n-Propyl-N-äthyl-, O-n-Propyl-N-n-propyl-, O-n-Propyl-N-iso-propyl-, O-n-Propyl-N-n-butyl-, O-iso-Propyl-N-äthyl-, O-iso-Propyl-N-n-propyl-, O-n-Butyl-N-äthyl-, 0-tert.-Butyl-N-äthylphosphorsäureesteramidchlorid sowie jeweils die entsprechenden Thionoanalogen.0,0-dimethyl-, 0,0-diethyl-, 0,0-di-n-propyl-, 0,0-di-isopropyl-, 0,0-di-n-butyl-, 0,0-di-iso-butyl-, O, O-di-tert-butyl-, O-ethyl-0-n-propyl-, O-ethyl-0-iso-propyl-, O-ethyl-O-sec-butyl-phosphoric acid ester chloride, as well as O-methyl-, O-ethyl-, O-n-propyl-, O-iso-propyl-, O-n-butyl-, O-sec.-butyl, O-iso-butyl or O-tert-butyl methane or -ethane, -n-propane, -iso-propane, -n-butane, -iso-butane, -see.-butane, -tert.- butane or -phenyl-phosphonic acid ester chloride, also O-methyl-N-methyl-, O-methyl-N-ethyl-, 0-methyl-N-n-propyl-, O-methyl-N-iso-propyl-, O-methyl-N-n-butyl-, O-ethyl-N-methyl-, O-ethyl-N-ethyl-, O-ethyl-N-n-propyl, 0-ethyl-N-iso-propyl-, O-ethyl-N-n-butyl-, O-ethyl-N-secbutyl-, O-n-propyl-N-methyl-, O-n-propyl-N-ethyl-, O-n-propyl-N-n-propyl-, O-n-Propyl-N-iso-propyl-, O-n-Propyl-N-n-butyl-, O-iso-propyl-N-ethyl, O-iso-propyl-N-n-propyl, O-n-butyl-N-ethyl, 0-tert-butyl-N-ethylphosphoric acid ester amide chloride as well as the corresponding thiono analogues in each case.
Die zum Teil neuen i-Phenyl-J-hydroxy^-alkenylmercaptotriazole der Formel (III) können nach prinzipiell bekannten Verfahren hergestellt werden. Beispielsweise setzt man Halogenkohlensäurealkylester mit Kaliumrhodanid und anschließend mit Phenylhydrazon zu dem Zwischenprodukt der FormelThe partly new i-phenyl-J-hydroxy ^ -alkenylmercaptotriazoles of the formula (III) can be prepared by processes which are known in principle. For example, halogenated carbonic acid alkyl esters are used with potassium rhodanide and then with phenylhydrazone to give the intermediate of the formula
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um, woraus dann durch Reaktion mit den entsprechenden Halogen alkenen in Gegenwart von Alkoholaten die gewünschten Hydroxytriazole (III) hergestellt werden können.um, from which then by reaction with the appropriate halogen alkenes in the presence of alcoholates, the desired hydroxytriazoles (III) can be prepared.
Als Beispiele für verfahrensgemäß umzusetzende Triazolderivate (III) seien im einzelnen genannt: 1-Phenyl-3-hydroxy-5-allylmercapto-, -5- t>uten(2' )yl-mercapto-, -5-/2'-niethyl-propen-(2') yl-mercaptqT-triazol (1,2,4).Specific examples of triazole derivatives (III) to be reacted according to the process include: 1-phenyl-3-hydroxy-5-allylmercapto-, -5- t> uten (2 ') yl-mercapto-, -5- / 2'-niethyl-propen- (2') yl-mercaptqT-triazole (1,2,4).
Das Herstellungsverfahren wird bevorzugt unter Mitverwendung geeigneter Lösungs- und Verdünnungsmittel durchgeführt. Als solche kommen praktisch alle inerten organischen Solventien in Frage. 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, Dioxan,· ferner Ketone, beispielsweise Aceton, Methyläthyl-, Methylisopropyl- und Methylisobutylketon, außerdem Nitrile, wie Aceto- und Propionitril.The production process is preferably carried out using suitable solvents and diluents. as practically all inert organic solvents can be used. 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, dioxane, furthermore ketones, e.g. acetone, Methyl ethyl, methyl isopropyl and methyl isobutyl ketone, as well Nitriles such as aceto- and propionitrile.
Als Säureakzeptoren können alle üblichen Säurebindemittel Verwendung finden. Besonders bewährt haben sich Alkalicarbonate und -alkoholate, wie Natrium- und Kaliumcarbonat, -methylat bzw. -äthylat, ferner aliphatische, aromatische oder heterocyclische Amine, beispielsweise Triäthyl- und Trimethylamin, Dimethylanilin,■Dimethylbenzylamin und Pyridin.All customary acid binders can be used as acid acceptors. Alkali carbonates have proven particularly useful and alcoholates, such as sodium and potassium carbonate, methylate or ethylate, and also aliphatic, aromatic or heterocyclic ones Amines, for example triethylamine and trimethylamine, dimethylaniline, ■dimethylbenzylamine and pyridine.
Die Reaktionstemperatur kann innerhalb eines größeren Bereiches variiert werden. Im allgemeinen arbeitet man zwischen 0 und 120, vorzugsweise bei 30 bis 85° C1 The reaction temperature can be varied within a relatively wide range. In general, the reaction is preferably carried out between 0 and 120, wherein 30 to 85 ° C for 1
Zur Durchführung des Verfahrens setzt man die Ausgangskomponenten im allgemeinen in äquimolaren Mengen ein. Ein Überschuß der einen oder anderen Reaktionskomponente bringt keineTo carry out the process, the starting components are generally employed in equimolar amounts. An excess one or the other reaction component does not bring any
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wesentlichen Vorteile. Die Umsetzung wird bevorzugt in einem der angeführten Lösungsmittel in Gegenwart eines Säureakzeptors bei der angegebenen Temperatur unter Rühren durchgeführt und nach ein- bis mehrstündiger Reaktionsdauer meist bei erhöhten Temperaturen der Ansatz in üblicher Weise aufgearbeitet. Im allgemeinen gießt man das Reaktionsgemisch in Wasser, nimmt es in einem organischen Lösungsmittel, z.B. Methylenchlorid, auf, wäscht und trocknet die organische Phase und destilliert das Lösungsmittel unter vermindertem Druck ab.substantial advantages. The reaction is preferably carried out in one of the solvents listed in the presence of an acid acceptor carried out at the specified temperature with stirring and after one to several hours of reaction time usually at increased Temperatures of the batch worked up in the usual way. In general, the reaction mixture is poured into water and taken it in an organic solvent, e.g. methylene chloride, washes and dries the organic phase and distilled the solvent from under reduced pressure.
Die neuen Verbindungen fallen oft in Form von Ölen an, die sich meist nicht unzersetzt destillieren lassen, jedoch durch sogenanntes "Andestillieren", d.h. 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. Einige Verbindungen fallen in kristalliner Form mit scharfem Schmelzpunkt an.The new compounds are often obtained in the form of oils, which can usually not be distilled without decomposition, but using what is known as something "Incipient distillation", i.e. prolonged heating under reduced pressure to moderately elevated temperatures from the last volatile components and can be cleaned in this way. The refractive index is used to characterize them. Some compounds are obtained in crystalline form with a sharp melting point.
Wie bereits mehrfach erwähnt, zeichnen sich die erfindungsgemäßen O-Triazol-(thiono)-phosphor(phosphon)-säureester bzw. -esteramide (I) durch eine hervorragende insektizide, auch bodeninsektizide, akarizide und nematizide Wirksamkeit aus. Sie wirken nicht nur gegen Pflanzen-, Hygiene- und Vorratsschädlinge, sondern auch auf dem veterinärmedizinischen Sektor gegen tierische Parasiten (Ektoparasiten), wie parasitierende Fliegenlarven und besitzen bei geringer Phytotoxizität sowohl eine gute Wirkung gegen saugende als auch fressende Insekten sowie Milben.As already mentioned several times, the O-triazole (thiono) phosphorus (phosphonic) acid esters according to the invention or -esteramide (I) is characterized by an excellent insecticidal, also soil insecticidal, acaricidal and nematicidal effectiveness. They are not only effective against plant, hygiene and stored product pests, but also in the veterinary sector against animal parasites (ectoparasites) such as parasitic fly larvae and possess both low phytotoxicity a good effect against sucking as well as eating insects and mites.
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.
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Zu den saugenden Insekten gehören im wesentlichen Blattläuse
(Aphidae) wie die grüne Pfirsichblattlaus (Myzus persicae),
die schwarze Bohnen- (Doralis fabae), Hafer- (Rhopalosiphum
padi), Erbsen- (Macrosiphum pisi) und Kartoffellaus (Macrosiphum solanifolii), ferner die Johannisbeergallen- (Cryptomyzus
korschelti), mehlige Apfel- (Sappaphis mali), mehlige Pflaumen-(Hyalopterus
arundinis) und schwarze Kirschenblattlaus (Myzus cerasi), außerdem Schild- und Schmierläuse (Coccina), z.B. die
Efeuschild- (Aspidiotus hederae) und Napfschildlaus (Lecanium hesperidum) sowie die Schmierlaus (Pseudococcus maritimus);
Blasenfüße (Thysanoptera) wie Hercinothrips femoralis und
Wanzen, beispielweeise die Rüben- (Piesma quadrata), Baumwoll-(Dysdercus
intermedius), Bett- (Cimex lectularius), Raub-(Rhodnius prolixus) und Chagaswanze (Triatoma infestans),
ferner Zikaden, wie Euscelis bilobatus und Nephotettix bipunctatus.
The sucking insects mainly include aphids
(Aphidae) such as the green peach aphid (Myzus persicae),
the black bean (Doralis fabae), oat (Rhopalosiphum
padi), pea (Macrosiphum pisi) and potato mouse (Macrosiphum solanifolii), also the currant gall (Cryptomyzus korschelti), floury apple (Sappaphis mali), floury plum (Hyalopterus arundinis) and black cherry aphid (Myzus cerasi), as well as shield - and mealybugs (Coccina), for example the ivy shield louse (Aspidiotus hederae) and cup scale louse (Lecanium hesperidum) as well as the mealybug (Pseudococcus maritimus);
Bladder feet (Thysanoptera) such as Hercinothrips femoralis and
Bed bugs, for example beet bugs (Piesma quadrata), cotton bugs (Dysdercus intermedius), bed bugs (Cimex lectularius), predatory bugs (Rhodnius prolixus) and chagas bugs (Triatoma infestans),
also cicadas such as Euscelis bilobatus and Nephotettix bipunctatus.
Bei den beißenden Insekten wären vor allem zu nennen Schmetterlingsraupen
(Lepidoptera) Vie die Kohlschabe (Plutella maculipennis), der Schwammspinner (Lymantria dispar), Goldafter
(Euproctis chrysorrhoea) und Ringelspinner (Malacosoma neustria),
weiterhin die Kohl- (Mamestra brassicae) und die Saateule (Agrotis segetum), der große Kohlweißling (Pieris brassicae),
kleine Prostspanner (Cheimatobia brumata), Eichenwickler (Tortrix viridana), der Heer- (Laphygma frugiperda) und aegyptische
Baumwöllwurm (Prodenia litura), ferner die Gespinst-(Hyponomeuta
padella), Mehl- (Ephestia kühniella ) und große
Wachsmotte (Galleria mellonella),Among the biting insects, butterfly caterpillars (Lepidoptera) should be mentioned above all: the cabbage moth (Plutella maculipennis), the gypsy moth (Lymantria dispar), and gold juicers
(Euproctis chrysorrhoea) and ring moth (Malacosoma neustria), furthermore the cabbage (Mamestra brassicae) and the seed owl (Agrotis segetum), the large cabbage white butterfly (Pieris brassicae), small prostitutes (Cheimatobia brumata), oak moth (Tortrix viridana), the large cabbage white butterfly (Pieris brassicae) - (Laphygma frugiperda) and Egyptian cottonworm (Prodenia litura), also the web (Hyponomeuta padella), flour (Ephestia kühniella) and large ones
Wax moth (Galleria mellonella),
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Weiterhin zählen zu den beißenden Insekten Käfer (Coleoptera) z.B. Korn- (Sitophilus granarius = Calandra granaria), Kartoffel- (Leptinotarsa decemlineata), Ampfer- (Gastrophysa viridula), Meerrettichblatt- (Phaedon cochleariae), Rapsglanz-(Meligethes aeneus), Himbeer- (Byturus tomentosus), Speisebohnen- (Bruchidius = Acanthoscelides obtectus), Speck-(Dermestes frischi), Khapra- (Trogoderma granarium), rotbrauner Reismehl- (Tribolium castaneum), Mais- (Calandra oder Sitophilus zeamais), Brot- (Stegobium paniceum), gemeiner Mehl- (Tenebrio molitor) und Getreideplattkäfer (Oryzaephilus surinamensis), aber auch im Boden lebende Arten z. B. Drahtwürmer (Agriotes spec.) und Engerlinge (Melolontha melolontha); Schaben wie die Deutsche (ELattella germanica), Amerikanische (Periplaneta americana), Madeira- (Leucophaea oder Rhyparobia maderae), Orientalische (Blatta'orientalis), Riesen- (Blaberus giganteus) und schwarze Riesenschabe (Blaberus fuscus) sowie Henschoutedenia flexivitta; ferner Orthopteren z.B. das Heimchen (Gryllus domesticus); Termiten wie die Erdtermite (Reticulitermes flavipes) und Hymenopteren wie Ameisen, beispielsweise die Wiesenameise (Lasius niger).Furthermore, the biting insects include beetles (Coleoptera) e.g. grain (Sitophilus granarius = Calandra granaria), Potato (Leptinotarsa decemlineata), dock (Gastrophysa viridula), horseradish leaf (Phaedon cochleariae), rapeseed (Meligethes aeneus), raspberry (Byturus tomentosus), table bean (Bruchidius = Acanthoscelides obtectus), Bacon (Dermestes frischi), khapra (Trogoderma granarium), red-brown rice flour (Tribolium castaneum), corn (Calandra or Sitophilus zeamais), bread (Stegobium paniceum), common flour (Tenebrio molitor) and grain beetle (Oryzaephilus surinamensis), but also species living in the ground such. B. wireworms (Agriotes spec.) And white grubs (Melolontha melolontha); Cockroaches like that German (ELattella germanica), American (Periplaneta americana), Madeira (Leucophaea or Rhyparobia maderae), Oriental (Blatta'orientalis), giant (Blaberus giganteus) and giant black cockroach (Blaberus fuscus) and Henschoutedenia flexivitta; furthermore orthoptera e.g. the cricket (Gryllus domesticus); Termites such as the terrestrial termites (Reticulitermes flavipes) and Hymenoptera such as ants, for example the Meadow ant (Lasius niger).
Die Dipteren umfassen im wesentlichen Fliegen wie die Tau-(Drosophila melanogaster), Mittelmeerfrucht- (Ceratitis capitata), Stuben- (Musca domestica), kleine Stuben- (Fannia canicularis), Glanz- (Phormia regina) und Schmeißfliege (Calliphora erythrocephala) sowie den Wadenstecher (Stomoxys calcitrans); ferner Mücken, z.B. Stechmücken wie die Gelbfieber- (Aedes aegypti), Haus- (Culex pipiens) und Malariamücke (Anopheles stephensi)o The Diptera essentially include flies such as the dew (Drosophila melanogaster), Mediterranean fruit (Ceratitis capitata), room (Musca domestica), small room (Fannia canicularis), glossy (Phormia regina) and blowfly (Calliphora erythrocephala) as well the calf stick (Stomoxys calcitrans); also mosquitoes, e.g. mosquitoes such as the yellow fever (Aedes aegypti), house mosquito (Culex pipiens) and malaria mosquito (Anopheles stephensi) etc.
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Zu den Milben (Acari) zählen besonders die Spinnmilben (Tetranychidae) wie die Bohnen- (Tetranychus telarius = Tetranychus althaeae oder Tetranychus urticae) und die Obstbaumspinnmilbe (Paratetranychus pilosus = Panonychus ulmi), Gallmilben, z.B. die Johannisbeergallmilbe (Eriophyes ribis) und Tarsonemiden beispielsweise die Triebspitzenmilbe (Hemitarsonemus latus) und Cyclamenmilbe (Tarsonemus pallidus); schließlich Zecken wie die Lederzecke (Ornithodorus moubata).The mites (Acari) include especially the spider mites (Tetranychidae) such as the bean (Tetranychus telarius = Tetranychus althaeae or Tetranychus urticae) and the fruit tree spider mite (Paratetranychus pilosus = Panonychus ulmi), Gall mites, e.g. the currant gall mite (Eriophyes ribis) and tarsonemids, for example the shoot tip mite (Hemitarsonemus latus) and cyclamen mite (Tarsonemus pallidus); finally ticks like the leather tick (Ornithodorus moubata).
Bei der Anwendung gegen Hygiene- und Vorratsschädlinge, besonders Fliegen und Mücken, zeichnen sich die Verfahrensprodukte außerdem·durch eine hervorragende Residualwirkung auf Holz und Ton sowie eine gute Alkalistabilität auf gekalkten Unterlagen aus.When used against hygiene and storage pests, especially flies and mosquitoes, the process products are also characterized by an excellent residual effect on wood and clay as well as good alkali stability on limed substrates.
Die erfindungsgemäßen Wirkstoffe haben bei geringer Warmblütertoxizität starke nematizide Eigenschaften und können deshalb zur Bekämpfung von Nematoden, insbesondere phytopathogenen Nematoden verwendet werden. Dazu gehören im wesentlichen Blattnematoden (Arphelenchoides), wie das Chrysanthemumälchen (A. ritzemabosi), das Erdbeerälchen (A. fragariae), das Reisälchen (A. oryzae); Stengelnematöden (Ditylenchus), wie das Stockälchen (D. Dipsaci); Würzelgallennematoden (Meloldogyne), wie M. arenaria und M. incognita; zystenbildende Nematoden (Heterodera), wie die Kartoffelnematode (H. rostochiensis), die Rübennematode (H. schachtii); sowie freilebende Würzelnematöden z.B. der Gattungen Pra- -tylenchus, Paratylenchus, Rotylenchus, Xiphinema und Radopholus. The active ingredients according to the invention have low toxicity to warm-blooded animals strong nematicidal properties and can therefore be used to control nematodes, especially phytopathogenic Nematodes are used. These essentially include leaf nematodes (Arphelenchoides), such as the chrysanthemum males (A. ritzemabosi), the strawberry elbow (A. fragariae), the rice elbow (A. oryzae); Stem nematodes (Ditylenchus), like the little stick (D. Dipsaci); Root-knot nematodes (Meloldogyne) such as M. arenaria and M. incognita; cyst-forming nematodes (Heterodera), such as the potato nematode (H. rostochiensis), the beet nematode (H. schachtii); as well as free-living root nematodes e.g. of the genera Pra- -tylenchus, Paratylenchus, Rotylenchus, Xiphinema and Radopholus.
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Die erfindungsgemäßen Wirkstoffe können in die üblichen Formulierungen übergeführt werden, wie Lösungen, Emulsionen, Suspensionen, Pulver, Pasten und Granulate. Diese werden in bekannter Weise hergestellt, z.B. 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, Benzol oder Alkylnaphthaline, chlorierte Aromaten oder chlorierte aliphatische Kohlenwasserstoffe, wie Chlorbenzole, Chloräthylene oder Methylenchlorid,The active compounds according to the invention can be used in the customary formulations such as solutions, emulsions, suspensions, powders, pastes and granulates. These are in produced in a known way, e.g. by mixing the active ingredients with extenders, i.e. liquid solvents, liquefied gases under pressure and / or solid carriers, optionally with the use of surface-active substances Agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. In case of Using water as an extender, organic solvents, for example, can also be used as auxiliary solvents. The main liquid solvents that can be used are: aromatics, such as xylene, toluene, benzene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or Methylene chloride,
aliphatische Kohlenwasserstoffe, wie Cyclohexan oder Paraffine, z.B. Erdölfraktionen, Alkohole, wie Butanol oder Glycol sowie deren Äther und Ester, Ketone, wie Aceton, Methyläthylketon, Methylisobutylketon oder Cyclohexanon, stark polare Lösungsmittel, wie Dimethylformamid und Dimethylsulfoxid, sowie Wasser; mit verflüssigten gasförmigen Streckmitteln oder Trägerstoffen sind solche Flüssigkeiten gemeint, welche bei normaler Temperatur und unter Normaldruck gasförmig sind, z.B. Aerosol-Treibgase, wie Halogenkohlenwasserstoffe, z.B. Freon; 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 Emulgier- und/oder schaumerzeugende Mittel: nichtionogene und anionische Emulgatoren, wie PoIyoxyäthylen-Fettsäure-Ester, Polyoxyäthylen-Fettalkohol-Äther, z.B. Alkylaryl-polyglykol-äther, Alkylsulfonate, Alkylsulfate, Arylsulfonate sowie Eiweißhydrolysate; als Dispergiermittel: z.B. Lignin, Sulfitablaugen und Methylcellulose. Die erfindungsgemäßen Wirkstoffe können in den Formulierungen in Mischung mit anderen bekannten Wirkstoffen vorliegen.aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. petroleum fractions, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strong polar solvents such as dimethylformamide and dimethyl sulfoxide, and water; with liquefied gaseous extenders or carrier substances are meant liquids which are gaseous at normal temperature and under normal pressure are, for example, aerosol propellants such as halogenated hydrocarbons, e.g., freon; as solid carriers: natural Powdered rock, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic ones Ground rock, such as finely divided silica, aluminum oxide and silicates; as an emulsifier and / or foam generator Medium: non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, Polyoxyethylene fatty alcohol ether, e.g. alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, Aryl sulfonates and protein hydrolysates; as dispersants: e.g. lignin, sulphite waste liquors and methyl cellulose. The active compounds according to the invention can be used in the formulations present in a mixture with other known active ingredients.
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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 %.
Die Wirkstoffe können als solche, in Form ihrer Formulierungen oder in den daraus "bereiteten Anwendung s for men, wie gebrauchsfertige Lösungen, Emulsionen, Schäume, Suspensionen, Pulver, Pasten, lösliche Pulver, Stäubmittel und Granulate angewendet werden. Die Anwendung geschieht in üblicher Weise, z.B. durch Verspritzen, Versprühen, Vernebeln, Verstäuben, Verstreuen, Verräuchern, Vergasen, Gießen, Beizen oder Inkrustieren. The active ingredients can be used as such, in the form of their formulations or in the applications prepared therefrom, such as ready-to-use solutions, emulsions, foams, suspensions, powders, pastes, soluble powders, dusts and granules be applied. It is used in the usual way, e.g. by spraying, atomizing, atomizing, dusting, Scattering, smoking, gasifying, pouring, pickling or encrusting.
Die Wirkstoffkonzentrationen in den anwendungsfertigen Zubereitungen können in größeren Bereichen variiert werden. Im allgemeinen liegen sie zwischen 0,0001 und 10 %, vorzugsweise zwischen 0,01 und 1 %. The active ingredient concentrations in the ready-to-use preparations can be varied over a wide range. In general, they are between 0.0001 and 10 %, preferably between 0.01 and 1 %.
Die Wirkstoffe können auch mit gutem Erfolg im Ultra-Low-Volume-Verfahren (ULV) verwendet werden, wo es möglich ist, Formulierungen bis zu 95 % oder sogar den 100 %-igen Wirkstoff allein auszubringen.The active ingredients can also be used with good success in the ultra-low-volume process (ULV), where it is possible to apply formulations of up to 95% or even the 100% active ingredient alone.
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In den folgenden Anwendungsbeispielen A bis D wurden die erfindungsgemäßen Wirkstoffe hinsichtlich ihrer Wirksamkeit gegen eine Reihe von Pflanzenschädlingen im Vergleich zu dem 0,0-Dimethyl-0-/3-methyl-pyrazol(5)yl/thionophosphorsäureester (A) und dem 0,0-Diäthyl-0-/l-isopropyl-5-methylmercapto(1,2,4) - tr iazol (3 )yl/-thiophosphorsäureester (B) getestet. Die neuen geprüften Substanzen werden in den verschiedenen Tests durch die jeweils in Klammer gesetzte Ziffer bezeichnet, die den fortlaufenden Nummern der Herstellungsbeispiele entspricht.In the following application examples A to D, the invention Active ingredients in terms of their effectiveness against a number of plant pests compared to the 0,0-dimethyl-0- / 3-methyl-pyrazol (5) yl / thionophosphoric acid ester (A) and the 0,0-diethyl-0- / l-isopropyl-5-methylmercapto (1,2,4) - triazol (3) yl / thiophosphoric acid ester (B) tested. The new substances tested are indicated in the various tests by the number in brackets which corresponds to the consecutive numbers of the production examples.
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Beispiel δExample δ
Plutella-TestPlutella 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 stated amount 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) taufeucht und besetzt sie mit Raupen der Kohlschabe (Plutella maculipennis).Cabbage leaves are sprayed with the active compound preparation (Brassica oleracea) becomes dewy and populates them with caterpillars of the cabbage moth (Plutella maculipennis).
Nach den angegebenen Zeiten wird der Abtötungsgrad in % bestimmt. Dabei bedeutet 100 %, daß alle Raupen getötet wurden, während 0 % angibt, daß keine Raupen getötet wurden.After the specified times, the degree of destruction is determined in % . 100 % means that all of the caterpillars have been killed, while 0 % indicates that no caterpillars have been killed.
Wirkstoffe, Wirkstoffkonzentrationen, Auswertungszeiten und Resultate gehen aus der nachfolgenden Tabelle 1 hervor:Active ingredients, active ingredient concentrations, evaluation times and The results are shown in Table 1 below:
LeA 15 632LeA 15 632
50 9 8 45/102250 9 8 45/1022
Tabelle 1
(Plutella - Test) Table 1
(Plutella test)
Wirkstoff Wirkstoffkon- AbtötungsgradActive ingredient active ingredient killing degree
zentration in % in % nachcentering in% in%
3 Tagen3 days
(A) 0,1 0(A) 0.1 0
0,1 1000.1 100
0,1 1000.1 100
0,1 - 1000.1-100
(1O) 0,1 100 (1O) 0.1 100
^ 0,1 100^ 0.1 100
0,1 1000.1 100
0,1 1000.1 100
0,1 1000.1 100
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iSiS
Myzus-Test (Kontakt-Wirkung)Myzus test (contact effect)
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 werden Kohlpflanzen (Brassica oleracea), welche stark von der Pfirsichblattlaus (Myzus persicae) befallen sind, tropfnaß besprüht.Cabbage plants (Brassica oleracea), which are strongly dependent on the peach aphid (Myzus persicae) are infected, sprayed to runoff.
Nach den angegebenen Zeiten wird der Abtötungsgrad in % bestimmt. Dabei bedeutet 100 %, daß alle Blattläuse abgetötet wurden, 0 % bedeutet, daß keine Blattläuse abgetötet wurden.After the specified times, the degree of destruction is determined in % . 100 % means that all aphids have been killed, 0 % means that none of the aphids have been killed.
Wirkstoffe, Wirkstoffkonzentrationen, Auswertungszeiten und Resultate gehen aus der nachfolgenden Tabelle 2 hervor:Active ingredients, active ingredient concentrations, evaluation times and The results are shown in Table 2 below:
LeA 15 632LeA 15 632
-15--15-
5 0 9845/10225 0 9845/1022
Tabelle 2
(Myzus- Test) Table 2
(Myzus test)
Wirkstoff Wirkstoffkonzen- AbtötungsgradActive ingredient active ingredient concentration degree of destruction
tration in % in % nach 1 Tagtration in% in% after 1 day
(A) 0,1 0(A) 0.1 0
(4) 0,1 100(4) 0.1 100
(2) 0,1 100(2) 0.1 100
(3) 0,1 100 (10) 0,1 100(3) 0.1 100 (10) 0.1 100
(8) 0,1 100 (7) 0,1 100(8) 0.1 100 (7) 0.1 100
(9) 0,1 100(9) 0.1 100
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Grenzkontrations-Test / Bodeninsekten Testinsekt: Phorbia antiqua-Maden im BodenBorder control test / soil insect test insect: Phorbia antiqua maggots in the soil
Lösungsmittel: 3 Gewichtsteile AcetonSolvent: 3 parts by weight of acetone
Emulgator: 1 Gewichtsteil AlkylarylpoIyglykolatherEmulsifier: 1 part by weight of alkylaryl polyglycol ethers
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit der angegebenen Menge Lösungsmittel, gibt die angegebene Menge Emulgator zu und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration. Die Wirkstoffzubereitung wird innig mit dem Boden vermischt. Dabei spielt die Konzentration des Wirkstoffes in der Zubereitung praktisch keine Rolle, entscheiden! ist allein die Wirkstoffgewichtsmenge pro Volumeneinheit Boden, welche in ppm angegeben wird (z.B. mg/l). Man füllt den Boden in Töpfe und läßt die Töpfe bei Raumtemperatur stehen. Nach 24 Stunden werden die Testtiere in den behandelten Boden gegeben und nach weiteren 48 Stunden wird der Wirkungsgrad des Wirkstoffes durch Auszählen der toten und lebenden Testinsekten in % bestimmt. Der Wirkungsgrad ist 100 %, wenn alle Testinsekten abgetötet worden sind, er ist 0 %, wenn noch genau so viele Testinsekten leben wie bei der Kontrolle.To produce an appropriate preparation of active ingredient, 1 part by weight of active ingredient is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration. The active ingredient preparation is intimately mixed with the soil. The concentration of the active ingredient in the preparation is practically irrelevant, it is up to you! is only the amount of active substance by weight per unit volume of soil, which is given in ppm (eg mg / l). The bottom is filled into pots and the pots are left to stand at room temperature. After 24 hours the test animals are placed in the treated soil and after a further 48 hours the degree of effectiveness of the active ingredient is determined in % by counting the dead and living test insects. The efficiency is 100 % if all test insects have been killed, it is 0 % if just as many test insects are still alive as in the control.
Wirkstoffe, Aufwandmengen und Resultate gehen aus der nachfolgenden Tabelle 3 hervor:Active ingredients, application rates and results are based on the following Table 3 shows:
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(Phorbia antiqua-Maden im Boden)(Phorbia antiqua maggots in the ground)
tration in ppmActive ingredient concentrations
tration in ppm
in % Degree of destruction
in %
LeA 15 632LeA 15 632
-18--18-
509845/10 22509845/10 22
Test mit parasitierenden FliegenlarvenTest with parasitic fly larvae
Lösungsmittel: 35 Gewichtsteile ÄthylenpolyglykolmonomethylätherSolvent: 35 parts by weight of ethylene polyglycol monomethyl ether
35 Gewichtsteile Nonylphenolpolyglykoläther35 parts by weight of nonylphenol polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 30 Gewichtsteile der' betreffenden aktiven Substanz mit der angegebenen Menge Lösungsmittel, das den oben genannten Anteil Emulgator enthält und verdünnt das so erhaltene Konzentrat mit Wasser auf die gewünschte Konzentration.To produce an appropriate preparation of the active substance, 30 parts by weight of the active substance in question are mixed with the specified amount of solvent which contains the above-mentioned portion of emulsifier and dilutes the resultant Concentrate with water to the desired concentration.
Etwa 20 Fliegenlarven (Lucilia cuprina) werden in ein Teströhrchen gebracht, welches ca. 2 cm Pferdemuskulatur enthält. Auf dieses Pferdefleisch werden 0,5 ml der Wirkstoffzubereitung gebracht. Nach 24 Stunden wird der Abtötungsgrad in % bestimmt. Dabei bedeuten 100 %, daß alle, und 0 %, daß keine Larven abgetötet worden sind.About 20 fly larvae (Lucilia cuprina) are placed in a test tube which contains approx. 2 cm of horse muscles. 0.5 ml of the active compound preparation are placed on this horse meat. The degree of destruction is determined in % after 24 hours. 100 % means that all larvae have been killed and 0% that none of the larvae have been killed.
Wirkstoffe, Wirkstoffkonzentrationen und Resultate gehenaus der nachfolgenden Tabelle 4 hervor:Active ingredients, active ingredient concentrations and results go out of the Table 4 below:
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toto
(Test mit parasit ierenden Fliegenlarven)(Test with parasitic fly larvae)
Wirkstoff Wirkstoffkonzen- Atitötungsgrad, in % Active ingredient active ingredient concentration degree of atitization, in %
tration in ppm (Lucilia cuprina res. )tration in ppm (Lucilia cuprina res.)
(4) 100 100(4) 100 100
30 10030 100
10 10010 100
(3) 100 , 100(3) 100, 100
100100
100100
3 <503 <50
LeA 15 632 -20- LeA 15 632 -20-
509845/1022509845/1022
CTCT
SCH, -C=CK..SCH, -C = CK ..
Zu einer Mischung aus 24,7 g (0,1 Mol) 1-Phenyl-3-hydroxy-5-Z2l-metbyl-propen(2)yl —mercaptoj-'b^iazoi (1,2,4) in 200 ecm Acetonitril fügt man 16 g Kaliumcarbonat und 19 g (0,1 Mol) 0,0-Diäthylthionophosphorsäurediesterchlorid, gießt nach 4 stündigem Rühren bei 80° C das Reaktionsgemisch in Wasser und nimmt es in Methylenchlorid auf. Die organische Phase wird gewaschen und getrocknet. Anschließend destilliert man das Lösungsmittel unter vermindertem Druck ab. Der Rückstand wird "andestilliert". Man erhält so 28 g (70 % der Theorie) 0,0-Diäthyl-0-/F-phenyl-5-( 2l -methyl-propen ( 2 )yl-mercapto") -tr iazol (3)yl7-thionophosphorsäureester mit dem Brechungsindex ^1 : 1,5593.To a mixture of 24.7 g (0.1 mol) of 1-phenyl-3-hydroxy-5-Z2 l -metbyl-propen (2) yl-mercaptoj-'b ^ iazoi (1,2,4) in 200 16 g of potassium carbonate and 19 g (0.1 mol) of 0,0-diethylthionophosphoric acid diester chloride are added to ecm acetonitrile, and after stirring for 4 hours at 80 ° C., the reaction mixture is poured into water and taken up in methylene chloride. The organic phase is washed and dried. The solvent is then distilled off under reduced pressure. The residue is "partially distilled". 28 g (70 % of theory) of 0,0-diethyl-O- / F-phenyl-5- (2 l -methyl-propen (2) yl-mercapto ") -triazol (3) yl7-thionophosphoric acid ester are obtained in this way with the refractive index ^ 1 : 1.5593.
Analog Beispiel 1 können die folgenden Verbindungen der FormelAnalogously to Example 1, the following compounds of the formula
hergestellt werden:getting produced:
LeA 15 652 _21- LeA 15 652 _21-
509845/1022509845/1022
Nr.Bexsplel R
No.
(Schmelzpunkt, Bre
chungsindex)Phys ically. Data:
(Melting point, bre
ching index)
nD22nd
n D
nD«22
n D
nD"21
n D
nD21
n D
nD22nd
n D
nD«22
n D
nD«22
n D
nD21
n D
nD«21
n D
Die Herstellung der als Ausgangsstoffe Verwendung findenden Hydroxytriazolderivate (III) kann z.B. in nachstehender Weise erfolgen: The hydroxytriazole derivatives (III) used as starting materials can be prepared, for example, in the following manner:
LeA LeA 15 15th 652652
-22--22-
509845/1022509845/1022
Zu einer Aufschlämmung von 96 g (1 Mol) getrocknetem Ealiumrhodanid in 500 ml Aceton fügt man 109 g Chlorkohlensäureäthylester, wobei die Reaktionstemperatur auf 30 bis 40 C gehalten wird. Die Reaktionsmischung wird über Macht gerührt und dann mit einer folgendermaßen bereiteten Phenylhydrazon-Lösung versetzt: 108 g Phenylhydrazin werden bei 40 bis 45 C in 200 ml Aceton gegeben, die Lösung wird drei Stunden gerührt und in Benzol gegossen. Nach dem Trocknen wird das Lösungsmittel abgedampft, und der Rückstand mit der obigen Reaktionsmischung vereinigt. Nach Rühren über Nacht wird die Lösung filtriert, das Lösungsmittel verdampft und der Rückstand in einer Mischung aus 800 ml Wasser und 100 ml Salzsäure 30 Minuten unter Rückfluß gekocht. Nach dem Abkühlen der Mischung wird der Niederschlag abgesaugt und aus Acetonitril umkristallisiert. Man erhält 48 g (25 % der Theorie) i-Phenyl-3-oxo-5-thio-triazolidin(1,2,4) mit dem Schmelzpunkt 235° C.109 g of ethyl chlorocarbonate are added to a suspension of 96 g (1 mol) of dried ealium rhodanide in 500 ml of acetone, the reaction temperature being kept at 30 to 40.degree. The reaction mixture is stirred over power and then treated with a phenylhydrazone solution prepared as follows: 108 g of phenylhydrazine are added to 200 ml of acetone at 40 to 45 ° C., the solution is stirred for three hours and poured into benzene. After drying, the solvent is evaporated and the residue is combined with the above reaction mixture. After stirring overnight, the solution is filtered, the solvent is evaporated and the residue is refluxed for 30 minutes in a mixture of 800 ml of water and 100 ml of hydrochloric acid. After the mixture has cooled, the precipitate is filtered off with suction and recrystallized from acetonitrile. 48 g (25 % of theory) of i-phenyl-3-oxo-5-thio-triazolidine (1,2,4) with a melting point of 235 ° C. are obtained.
S-CH2 -C=CH2 S-CH 2 -C = CH 2
Zu 97 g "(0,5 Mol) des wie unter a) beschriebenen gewonnenen Produktes in 400 ml Triäthylamin fügt man 0,5 Mol einer Natriummethylat-Lösung und anschließend bei 50 bis 60° C 46 g 1-Chlor-2-methyl-propen(2). Die Reaktionslösung wird 3 Stunden bei 70 bis 75° C gerührt, in Wasser gegossen, filtriert, der Rückstand getrocknet und aus Acetonitril umkristallisiert. Man erhält 75 g (61 % der Theorie) 1-Phenyl-3-hydro3cy-5-/5'-methylpropen(2)ylmercapto7-triazol(1,2,4) mit dem Schmelzpunkt 141° C.To 97 g "(0.5 mol) of the product obtained as described under a) in 400 ml of triethylamine is added 0.5 mol of a sodium methylate solution and then at 50 to 60 ° C 46 g of 1-chloro-2-methyl- propene (2). The reaction solution is stirred for 3 hours at 70 to 75 ° C., poured into water, filtered, the residue dried and recrystallized from acetonitrile to give 75 g (61 % of theory) 1-phenyl-3-hydro3cy- 5- / 5'-methylpropene (2) ylmercapto7-triazole (1,2,4) with a melting point of 141 ° C.
In analoger Weise können die Verbindungen folgender FormelnThe compounds of the following formulas can be used in an analogous manner
LeA 15 632 -23- LeA 15 632 -23-
509845/1022509845/1022
Κ_/S-CH2-CH=CH2 Κ_ / S-CH 2 -CH = CH 2
mit dem Schmelzpunkt 137° C undwith a melting point of 137 ° C and
-CHjj -CH=CE-CH3 -CHjj -CH = CE-CH 3
mit dem Schmelzpunkt 145 hergestellt werden.with a melting point of 145 can be produced.
LeA 15 632 LeA 15 632
-24--24-
509845/1022509845/1022
Claims (6)
R'' Alkenyl mit 1 bis 6 Kohlenstoffatomen und X ein Sauerstoff- oder Schwefelstoffatom bedeutet.Carbon atoms or phenyl
R ″ denotes alkenyl with 1 to 6 carbon atoms and X denotes an oxygen or sulfur atom.
Priority Applications (22)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2419623A DE2419623A1 (en) | 1974-04-24 | 1974-04-24 | 0-TRIAZOLYL- (THIONO) -PHOSPHORUS (PHOSPHONE) ACID ESTER OR. -ESTERAMIDE, THE PROCESS FOR THEIR MANUFACTURING AND THEIR USE AS INSECTICIDE, ACARICIDE AND NEMATICIDE |
| AU79787/75A AU482568B2 (en) | 1974-04-24 | 1975-04-03 | Novel [thiono] - phosphoric [phosphonic] acid esters and ester amides, their preperation and their use as insecticides, acaridides and nematicides |
| SU752121990A SU673142A3 (en) | 1974-04-24 | 1975-04-10 | Insecto-cariocide-nematocide agent |
| GB1543575A GB1454490A (en) | 1974-04-24 | 1975-04-15 | Thiono-phosphoric-phosphonic acid esters and ester amides their preparation and their use as insecticides acaricides and nema ticides |
| IL7547131A IL47131A (en) | 1974-04-24 | 1975-04-21 | 1,2,4-triazolyl phosphoric thionophosphoric phosphonic and thionophosphonic acid esters and ester amides their preparation and their use as insecticides acaricides and nematicides |
| BE155591A BE828162A (en) | 1974-04-24 | 1975-04-21 | NEW ESTERS AND ESTERAMIDES OF O-TRIAZOLYL- (THIONO-PHOSPHORIC (PHOSPHONIC) ACIDS, THEIR PREPARATION AND THEIR APPLICATION AS INSECTICIDES, |
| CH506875A CH576987A5 (en) | 1974-04-24 | 1975-04-21 | |
| NL7504712A NL7504712A (en) | 1974-04-24 | 1975-04-21 | PROCESS FOR PREPARING NEW O-TRIAZOLYL (THIONO) PHOSPHORIC (PHOSPHON) ACID ESTERS OR ESTERA MIDS, AND THEIR USE AS ACTIVE INGREDIENTS OF INSECTICIDE, ACARICIDE AND NEMA TOCIDE PREPARATIONS. |
| TR18171A TR18171A (en) | 1974-04-24 | 1975-04-22 | 0-TRIAZOLIL (TIONO) -PHOSPHONIC ACID ESTERS AND ESTER AMIDES, A PROCEDURE FOR THE PREPARATION OF THESE AND THEIR USE AS INSECTIC, ACARAISID AND NEMATOSID |
| RO7582045A RO66670A (en) | 1974-04-24 | 1975-04-22 | PROCESS FOR OBTAINING ANY ESTERS, RESPECTIVELY, O-TRIAZOLYL (THINO) PHOSPHORIC ACID ESTERS (PHOSPHONIC) |
| DD185603A DD122319A5 (en) | 1974-04-24 | 1975-04-22 | |
| AT306875A AT330800B (en) | 1974-04-24 | 1975-04-22 | PROCESS FOR THE PRODUCTION OF NEW O-TRIAZOLYL- (THIONO) -PHOSPHORUS (PHOSPHONE) -AUCID ESTERS AND -ESTERAMIDES |
| LU72336A LU72336A1 (en) | 1974-04-24 | 1975-04-22 | |
| PL1975179886A PL93325B1 (en) | 1974-04-24 | 1975-04-23 | |
| ZA00752618A ZA752618B (en) | 1974-04-24 | 1975-04-23 | Novel(thiono)-phosphoric(phosphonic) acid esters and ester amides, their preparation and their use as insecticides acaricides and nematicides |
| JP50048729A JPS50148360A (en) | 1974-04-24 | 1975-04-23 | |
| BR3126/75D BR7502459A (en) | 1974-04-24 | 1975-04-23 | PROCESS TO PREPARE ESTERS OR STARCHES OF O-TRIAZOLYLIC ACID (THIONO) -Phosphoric (Phosphonic) Esters, as well as insecticidal, caracid and non-toxic compounds based on these |
| IE912/75A IE41334B1 (en) | 1974-04-24 | 1975-04-23 | Novel (thiono) - phosphoric (phosphonic) acid esters and ester amides their preparation and their use as insecticides acaricides and nematicides |
| DK174875A DK138231C (en) | 1974-04-24 | 1975-04-23 | INSECTICIDES, ACARICIDES AND NEMATODICIDES EFFICIENTS O-TRIAZOLYL- (THIONO) -PHOSPHOR (PHOSPHON)-ACID RESIDENTS OR -ESTERAMIDES FOR USE IN PLANT PROTECTION AND OTHER TECHNOLOGY |
| ES436876A ES436876A1 (en) | 1974-04-24 | 1975-04-23 | Thiono-phosphoric-phosphonic acid esters and ester amides their preparation and their use as insecticides acaricides and nema ticides |
| FR7512822A FR2268810B1 (en) | 1974-04-24 | 1975-04-24 | |
| HU75BA00003255A HU171548B (en) | 1974-04-24 | 1975-04-24 | Insecticide, acaricide and nematocide emulsions containing 0-triasolyl-bracket-thiono-phosphoric-bracket closed- and-bracket-thiono-phosphonic-bracket closed-acid-esters, and-ester-amides, and process for producing the active agents |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2419623A DE2419623A1 (en) | 1974-04-24 | 1974-04-24 | 0-TRIAZOLYL- (THIONO) -PHOSPHORUS (PHOSPHONE) ACID ESTER OR. -ESTERAMIDE, THE PROCESS FOR THEIR MANUFACTURING AND THEIR USE AS INSECTICIDE, ACARICIDE AND NEMATICIDE |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2419623A1 true DE2419623A1 (en) | 1975-11-06 |
Family
ID=5913715
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2419623A Pending DE2419623A1 (en) | 1974-04-24 | 1974-04-24 | 0-TRIAZOLYL- (THIONO) -PHOSPHORUS (PHOSPHONE) ACID ESTER OR. -ESTERAMIDE, THE PROCESS FOR THEIR MANUFACTURING AND THEIR USE AS INSECTICIDE, ACARICIDE AND NEMATICIDE |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS50148360A (en) |
| AT (1) | AT330800B (en) |
| BE (1) | BE828162A (en) |
| BR (1) | BR7502459A (en) |
| CH (1) | CH576987A5 (en) |
| DD (1) | DD122319A5 (en) |
| DE (1) | DE2419623A1 (en) |
| DK (1) | DK138231C (en) |
| ES (1) | ES436876A1 (en) |
| FR (1) | FR2268810B1 (en) |
| GB (1) | GB1454490A (en) |
| HU (1) | HU171548B (en) |
| IE (1) | IE41334B1 (en) |
| IL (1) | IL47131A (en) |
| LU (1) | LU72336A1 (en) |
| NL (1) | NL7504712A (en) |
| PL (1) | PL93325B1 (en) |
| RO (1) | RO66670A (en) |
| SU (1) | SU673142A3 (en) |
| TR (1) | TR18171A (en) |
| ZA (1) | ZA752618B (en) |
-
1974
- 1974-04-24 DE DE2419623A patent/DE2419623A1/en active Pending
-
1975
- 1975-04-10 SU SU752121990A patent/SU673142A3/en active
- 1975-04-15 GB GB1543575A patent/GB1454490A/en not_active Expired
- 1975-04-21 BE BE155591A patent/BE828162A/en unknown
- 1975-04-21 CH CH506875A patent/CH576987A5/xx not_active IP Right Cessation
- 1975-04-21 IL IL7547131A patent/IL47131A/en unknown
- 1975-04-21 NL NL7504712A patent/NL7504712A/en not_active Application Discontinuation
- 1975-04-22 AT AT306875A patent/AT330800B/en not_active IP Right Cessation
- 1975-04-22 LU LU72336A patent/LU72336A1/xx unknown
- 1975-04-22 RO RO7582045A patent/RO66670A/en unknown
- 1975-04-22 TR TR18171A patent/TR18171A/en unknown
- 1975-04-22 DD DD185603A patent/DD122319A5/xx unknown
- 1975-04-23 BR BR3126/75D patent/BR7502459A/en unknown
- 1975-04-23 JP JP50048729A patent/JPS50148360A/ja active Pending
- 1975-04-23 ES ES436876A patent/ES436876A1/en not_active Expired
- 1975-04-23 PL PL1975179886A patent/PL93325B1/pl unknown
- 1975-04-23 IE IE912/75A patent/IE41334B1/en unknown
- 1975-04-23 ZA ZA00752618A patent/ZA752618B/en unknown
- 1975-04-23 DK DK174875A patent/DK138231C/en active
- 1975-04-24 FR FR7512822A patent/FR2268810B1/fr not_active Expired
- 1975-04-24 HU HU75BA00003255A patent/HU171548B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL7504712A (en) | 1975-10-28 |
| PL93325B1 (en) | 1977-05-30 |
| IL47131A (en) | 1977-11-30 |
| ZA752618B (en) | 1976-04-28 |
| SU673142A3 (en) | 1979-07-05 |
| DK138231C (en) | 1979-01-15 |
| LU72336A1 (en) | 1976-03-17 |
| CH576987A5 (en) | 1976-06-30 |
| FR2268810B1 (en) | 1978-10-13 |
| ATA306875A (en) | 1975-10-15 |
| DD122319A5 (en) | 1976-10-05 |
| HU171548B (en) | 1978-02-28 |
| AT330800B (en) | 1976-07-26 |
| ES436876A1 (en) | 1976-12-01 |
| DK138231B (en) | 1978-07-31 |
| DK174875A (en) | 1975-10-25 |
| FR2268810A1 (en) | 1975-11-21 |
| GB1454490A (en) | 1976-11-03 |
| BE828162A (en) | 1975-10-21 |
| AU7978775A (en) | 1976-10-07 |
| IL47131A0 (en) | 1975-06-25 |
| IE41334L (en) | 1975-10-24 |
| JPS50148360A (en) | 1975-11-27 |
| IE41334B1 (en) | 1979-12-05 |
| RO66670A (en) | 1981-07-30 |
| BR7502459A (en) | 1976-03-09 |
| TR18171A (en) | 1976-11-01 |
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