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1. 发明授权

US4036956A O,S,N-tri-aliphatic hydrocarbon-thionothiolphosphoric acid ester amides and pesticidal composition and method 失效
标题翻译： O，S，N-三脂族烃硫代硫代磷酸酯酰胺和杀虫剂组成及方法
公开(公告)号：US4036956A
公开(公告)日：1977-07-19
申请号：US545658
申请日：1975-01-30
申请人： Claus Stolzer , Bernhard Homeyer , Ingeborg Hammann , Gunter Unterstenhofer
发明人： Claus Stolzer , Bernhard Homeyer , Ingeborg Hammann , Gunter Unterstenhofer
IPC分类号： C07F9/24 , A01N9/36 , C07F9/22
CPC分类号： C07F9/24
摘要： O,S,N-tri-aliphatic hydrocarbon-thionothiolphosphoric acid ester amides of the general formula ##STR1## in which R, R.sup.1 and R.sup.2, which may be the same or different, each is an alkyl, alkenyl or alkynyl radical with up to 6 carbon atoms, optionally substituted with at least one halo, phenyl, cyano, alkoxy, alkylmercapto, phenylmercapto or naphthylmercapto radical, the mercapto radicals being optionally chloro- or cyano-substituted,Which possess nematocidal, insecticidal, acaridical, fungicidal and mammalian-repellent properties.
摘要翻译： O，S，N-三脂族烃硫代硫代磷酸酯酰胺，其中R，R 1和R 2可以相同或不同，各自为烷基，烯基或炔基具有至多6个碳原子，任选被至少一个卤素，苯基，氰基，烷氧基，烷基巯基，苯巯基或萘基巯基自由基取代，巯基任选被氯代或氰基取代，其具有无毒的杀虫剂，杀虫剂，杀菌剂，马马里兰特产。

2. 发明授权

US3979512A S-(amidocarbonyl)-methyl-O-alkyl-monothiophosphoric acid ester amides 失效
标题翻译： S-（酰氨基羰基） - 甲基-O-烷基 - 一硫代磷酸酯酰胺
公开(公告)号：US3979512A
公开(公告)日：1976-09-07
申请号：US561589
申请日：1975-03-24
申请人： Claus Stolzer , Ingeborg Hammann , Gunter Unterstenhofer
发明人： Claus Stolzer , Ingeborg Hammann , Gunter Unterstenhofer
IPC分类号： C07F9/6533 , C07D295/10
CPC分类号： C07F9/6533
摘要： S-(amidocarbonyl)-methyl-O-alkyl monothiophosphoric acid ester amides of the formula ##EQU1## in which R and R' each independently is alkyl of 1 to 6 carbon atoms,R" is alkyl or alkenyl of 1 to 6 carbon atoms optionally carrying at least one chlorine,C.sub.1 -c.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylmercapto or nitrile radical,R"' is hydrogen or acyl, with the proviso that R"' is not hydrogen if R" is unsubstituted alkyl, orR" and R"' conjointly with the nitrogen atom to which they are attached form a heterocyclic ring, which possess insecticidal and acaricidal properties.
摘要翻译：式R-OO的S-（酰氨基羰基） - 甲基-O-烷基一硫代磷酸酯酰胺ANGLE P ANGLE R“（I）R'-NHS-CH2-CN ANGLE PARALLEL OR”'其中R和R' 各自独立地是1至6个碳原子的烷基，R“是1至6个碳原子的烷基或烯基，任选地带有至少一个氯，C 1 -C 6烷氧基，C 1 -C 6烷基巯基或腈基，R”'是氢或酰基，条件是如果R“是未取代的烷基，R”'不是氢，或者R“和R”与它们所连接的氮原子并用，形成杂环，其具有杀虫活性和杀螨属性。

3. 发明授权

US3993717A S-(alkoxycarbonyl)-alkyl-thiophosphoric acid ester amides 失效
标题翻译： S-（烷氧基羰基） - 烷基 - 硫代磷酸酯酰胺
公开(公告)号：US3993717A
公开(公告)日：1976-11-23
申请号：US386673
申请日：1973-08-08
申请人： Claus Stolzer , Wolfgang Behrenz , Ingeborg Hammann
发明人： Claus Stolzer , Wolfgang Behrenz , Ingeborg Hammann
IPC分类号： A01N57/28 , C07F9/24 , A01N9/36
CPC分类号： C07F9/24
摘要： S-(alkoxycarbonyl)-alkyl-thiophosphoric acid ester amides of the general formula ##EQU1## in which R, R' and R" each independently is alkyl of 1 to 10 carbon atoms or lower alkenyl,Y is hydrogen or lower alkyl,Y' is hydrogen, lower alkyl or --CH.sub.2 --CO--OR", andX is oxygen or sulfur,Which possess insecticidal and acaricidal properties.
摘要翻译：通式为R-OX的S-（烷氧基羰基） - 烷基 - 硫代磷酸酯酰胺，其中R，R'和R “各自独立地是1至10个碳原子的烷基或低级烯基，Y是氢或低级烷基，Y'是氢，低级烷基或-CH 2 -CO-OR”，X是氧或硫，其中无毒物和杀虫剂性质。

4. 发明授权

US4229580A Preparation of 1-azolyl-3,3-dimethyl-1-phenoxy-butan-2-ones 失效
标题翻译： 1-噻唑基-3,3-二甲基-1-苯氧基 - 丁-2-酮的制备
公开(公告)号：US4229580A
公开(公告)日：1980-10-21
申请号：US885053
申请日：1978-03-09
申请人： Hermann Arold , Hans-Ludwig Elbe , Eckart Kranz , Wolfgang Kramer , Jorg Stetter , Claus Stolzer , Rudolf Thomas
发明人： Hermann Arold , Hans-Ludwig Elbe , Eckart Kranz , Wolfgang Kramer , Jorg Stetter , Claus Stolzer , Rudolf Thomas
IPC分类号： A01N43/50 , A01N43/836 , C07D233/60 , C07D249/08 , C07D521/00
CPC分类号： C07D231/12 , C07D233/56 , C07D249/08
摘要： In the reaction of 1-chloro-3,3-dimethylbutan-2-one with a phenol to form an ether-ketone, halogenating it to form a halogenoether-ketone and reacting it with imidazole or 1,2,4-triazole to form a 1-azolyl-3,3-dimethyl-1-phenoxybutan-2-one of the formula ##STR1## in which X is N or CH,n is an integer from 0 to 4, andY each independently is halogen, phenyl, phenoxy, nitro, alkyl, alkoxy or cycloalkyl,the improvement which comprises effecting all steps successively in an aromatic hydrocarbon or chlorinated aliphatic or aromatic hydrocarbon as solvent without intermediate isolation. The products are obtained in high yield.
摘要翻译：在1-氯-3,3-二甲基丁-2-酮与苯酚反应形成醚 - 酮的反应中，将其卤化形成卤代醚 - 酮并与咪唑或1,2,4-三唑反应形成其中X为N或CH，n为0至4的整数，并且Y各自独立地为卤素，苯基，环烷基，环烷基，苯氧基，硝基，烷基，烷氧基或环烷基，其改进包括在芳族烃或氯化脂族或芳族烃作为溶剂中连续进行所有步骤而不中间分离。以高产率获得产品。

5. 发明授权

US4394309A Process for the preparation of N,N-dimethyl-N-(2-bromo-4-methylphenyl)-triazene 失效
标题翻译：制备N，N-二甲基-N-（2-溴-4-甲基苯基） - 三氮烯的方法
公开(公告)号：US4394309A
公开(公告)日：1983-07-19
申请号：US249247
申请日：1981-03-30
申请人： Claus Stolzer
发明人： Claus Stolzer
IPC分类号： C07C245/24 , C07C17/093 , C07C41/22 , C07C67/00 , C07C241/00 , C07C113/00 , C07C87/60 , C07C113/04
CPC分类号： C07C17/093 , C07C231/12 , C07C241/00
摘要： A process for the preparation of N,N-dimethyl-N'-(2-bromo-4-methyl-phenyl)-triazene of the formula ##STR1## comprising (a) reacting N-acetyl-p-toluidine of the formula ##STR2## with bromine at a temperature between about 0.degree. and 100.degree. C., to give the intermediate product of the formula ##STR3## (b) reacting the intermediate product with hydrochloric acid by either (i) adding a dilute solution of aqueous hydrochloric acid to the intermediate product in its reaction solution and heating the mixture to a temperature between about 50.degree. and 120.degree. C., or(ii) precipitating the intermediate product from its reaction solution by mixing with water and filtering off, and without purification or drying heating the precipitate with dilute aqueous hydrochloric acid to a temperature between about 50.degree. and 120.degree. C., thereby to form a solution of 2-bromo-4-methylaniline hydrochloride, (c) reacting the resulting aqueous solution with an alkali metal nitrite at a temperature between about -20.degree. and +30.degree. C., and (d) reacting the product with dimethylamine at a temperature between about 0.degree. and 50.degree. C.
摘要翻译：制备下式的N，N-二甲基-N' - （2-溴-4-甲基 - 苯基） - 三烯的方法，包括：（a）使下式的N-乙酰基 - 对甲苯胺，在约0℃至100℃的温度下加入溴，得到中间产物，其结构式如下：（b）使中间产物与盐酸反应，方法是（i）加入稀盐酸水溶液在其反应溶液中向中间产物加酸，并将混合物加热至约50至120℃的温度，或（ii）通过与水混合并过滤从而将其从反应溶液中沉淀出来，并且不经纯化或干燥，用稀盐酸水溶液将沉淀物加热至约50〜120℃，由此形成2-溴-4-甲基苯胺盐酸盐溶液，（c）使所得水溶液与碱金属亚硝酸盐在约-20℃的温度下 EG和+ 30℃，和（d）在约0℃至50℃的温度下使产物与二甲基胺反应。

6. 发明授权

US4013677A Preparation of 1,2,4-triazolyl-(1)-phenoxy-acyl-methanes 失效
标题翻译： 1,2,4-三唑基 - （1） - 苯氧基 - 甲基甲烷的制备
公开(公告)号：US4013677A
公开(公告)日：1977-03-22
申请号：US547429
申请日：1975-02-05
申请人： Claus Stolzer , Wolfgang Kramer , Karl Heinz Buchel , Werner Meiser
发明人： Claus Stolzer , Wolfgang Kramer , Karl Heinz Buchel , Werner Meiser
IPC分类号： A61K31/4196 , A61P31/10 , B01J23/00 , B01J27/00 , B01J31/00 , C07D249/08 , C07D521/00
CPC分类号： C07D231/12 , C07D233/56 , C07D249/08
摘要： A process for the preparation of a 1,2,4-triazolyl-(1)-phenoxy-acyl-methane of the formula ##STR1## in which R is alkyl or aryl,Each X independently is alkyl, halogen, alkoxycarbonyl, nitrile, phenyl or nitro, andn is an integer from 0 to 5,Comprising reacting a dihaloketone of the formula(Hal).sub.2 CH--CO--Rin whichHal is halogen, ##STR2## 1,2,4-TRIAZOLE AND WITH A PHENOL OF THE FORMULA T,0011 IN THE PRESENCE OF AN ACID-BINDING AGENT AND DILUENT, AT A TEMPERATURE OF ABOUT 0.degree. TO 150.degree. C. Advantageously the temperature is about 50.degree. to 90.degree. C and about 1 mole of the phenol, about 1 to 1.2 moles of the 1,2,4-triazole and about 2 to 3 moles of the acid-binding agent are used per mole of the dihaloketone.

7. 发明授权

US4388465A Preparation of phenoxy-azolyl-butanone derivatives 失效
标题翻译：苯氧基 - 唑基 - 丁酮衍生物的制备
公开(公告)号：US4388465A
公开(公告)日：1983-06-14
申请号：US300071
申请日：1981-09-08
申请人： Hans-Ludwig Elbe , Hermann Arold , Eckart Kranz , Claus Stolzer
发明人： Hans-Ludwig Elbe , Hermann Arold , Eckart Kranz , Claus Stolzer
IPC分类号： A01N43/50 , A01N43/653 , C07D233/60 , C07D249/08 , C07D521/00
CPC分类号： C07D231/12 , C07D233/56 , C07D249/08
摘要： In the preparation of a phenoxy-azolyl-butanone derivative of the formula ##STR1## in which X is a halogen atom,Y is a hydrogen or halogen atom, andAz is an imidazolyl radical or a 1,2,4-triazolyl radical,wherein dichloropinacolin of the formulaCl.sub.2 CH--CO--C(CH.sub.3).sub.3is reacted with an azole of the formulaAz--Hand a phenol of the formula ##STR2## in the presence of an acid-binding agent, the improvement which comprises carrying out the reaction in the presence of a water-immiscible organic solvent at a temperature between about 40.degree. and 150.degree. C., adding to the solvent at a temperature between about 0.degree. and +80.degree. C. a mineral acid, thereby to precipitate the mineral acid salt of the phenoxy-azolyl-butanone derivative, and separating such salt. Surprisingly the product does not hydrolyze when standing in contact with the mineral acid solution. The product is a known fungicide.
摘要翻译：在制备其中X是卤素原子的式“IMAGE”的苯氧基 - 唑基 - 丁酮衍生物的制备中，Y是氢或卤素原子，并且Az是咪唑基或1,2,4-三唑基，其中式Cl2CH-CO-C（CH3）3的二氯青霉素与酸结合剂存在下与式为Az-H的唑和式“IMAGE”的苯酚反应，其改进包括进行在与水不混溶的有机溶剂的存在下在约40℃至150℃的温度下反应，在约0℃至+ 80℃的温度下加入无机酸，从而沉淀出苯氧基 - 唑基 - 丁酮衍生物的无机酸盐，并分离此盐。令人惊讶的是，当与无机酸溶液接触时，产物不会水解。该产品是已知的杀真菌剂。

8. 发明授权

US4219511A Preparation of O,O-diethyl-O-(1-phenyl-2-cyano-prop-1-enyl)-thionophosphoric acid ester 失效
标题翻译：制备O，O-二乙基-O-（1-苯基-2-氰基 - 丙-1-烯基） - 硫代磷酸酯
公开(公告)号：US4219511A
公开(公告)日：1980-08-26
申请号：US29815
申请日：1979-04-13
申请人： Hans-Jochem Riebel , Claus Stolzer
发明人： Hans-Jochem Riebel , Claus Stolzer
IPC分类号： A01N57/14 , C07F9/165 , C07F9/173
CPC分类号： C07F9/173
摘要： In the preparation of O,O-diethyl-O-(1-phenyl-2-cyano-prop-1-enyl)-thionophosphoric acid ester by reacting a benzoic acid ester with propionitrile in the presence of an alkali metal alcoholate and then reacting the reaction mixture with O,O-diethyl-thionophosphoric acid diester chloride, the improvement which comprises employing about 5 to 50 moles of the propionitrile per mole of benzoic acid ester, distilling off the alcohol obtained during the reaction of propionitrile, benzoic acid ester and alcoholate before the addition of the O,O-diethyl-thionophosphoric acid diester chloride, and maintaining the volume of the reaction mixture approximately constant by adding propionitrile during the distillation. Advantageously the alcoholate is sodium methylate, ethylate or tert.-butylate or potassium methylate, ethylate or tert.-butylate, the reaction is effected at about 80.degree. to 120.degree. C., about 5 to 25 moles of propionitrile are employed per mole of benzoic acid ester, about 1 to 1.3 moles of benzoic acid ester and about 1 to 1.15 moles of alkali metal alcoholate are employed per mole of O,O-diethyl-thionophosphoric acid diester chloride, and the benzoic acid ester is the methyl ester or ethyl ester.
摘要翻译：在制备O，O-二乙基-O-（1-苯基-2-氰基 - 丙-1-烯基） - 硫代磷酸酯时，通过苯甲酸酯与丙腈在碱金属醇化物存在下反应，与O，O-二乙基 - 硫代磷酸二酯氯化物的反应混合物，其改进包括使用约5至50摩尔丙腈/摩尔苯甲酸酯，蒸馏出丙腈，苯甲酸酯和在加入O，O-二乙基 - 硫代磷酸二酯氯化物之前加入醇化物，并且在蒸馏期间通过加入丙腈将反应混合物的体积保持在约恒定。有利地，醇化物是甲醇钠，乙酸乙酯或叔丁醇钠或甲醇钾，乙酸乙酯或叔丁醇钾，反应在约80℃至120℃下进行，每摩尔环己烷使用约5至25摩尔丙腈每摩尔O，O-二乙基 - 硫代磷酸二酯氯化物使用苯甲酸酯，约1至1.3摩尔苯甲酸酯和约1至1.15摩尔碱金属醇化物，苯甲酸酯是甲酯或乙酯酯。

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