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    • 1. 发明授权
    • Process for the preparation of strobilurin intermediates
    • 制备嗜球果伞素中间体的方法
    • US06664422B1
    • 2003-12-16
    • US09857391
    • 2001-08-13
    • Rudolf WaditschatkaRené ZurflühEdward KelsallHugo ZieglerLinhua Wang
    • Rudolf WaditschatkaRené ZurflühEdward KelsallHugo ZieglerLinhua Wang
    • C07C24900
    • C07C249/08C07C45/00C07C49/233C07C251/48
    • The present invention relates to a novel improved process and intermediates for the process of preparing the oxime intermediates of formula (II) wherein R1 is hydrogen, fluoro or chloro, and R2 is methyl, ethyl, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy, cyano, fluoro, chloro or bromo. The novel process comprises diazotizing an aniline of formula (VI) reacting the resulting diazonium salt with isopropenylacetate of formula (X) and reacting the resulting ketone of formula (XI) with an organic nitrite in the presence of hydrogene chloride, and methylating the resulting ketooxime of formula (VIII) with a methylating agent and reacting the resulting O-methyl ketooxime of formula (IX) with hydroxylamine. The compounds of formula (II) are intermediates for highly active fungicides from the class of the strobilurins.
    • 本发明涉及制备式(II)的肟中间体的方法和中间体,其中R1是氢,氟或氯,R2是甲基,乙基,甲氧基,乙氧基,三氟甲基,三氟甲氧基,氰基, 氟,氯或溴。 该新方法包括使式(Ⅵ)的苯胺重氮化,使得到的重氮盐与式(X)的异丙烯基乙酸酯反应,并使所得的式(Ⅺ)酮与有机亚硝酸酯在氯化氢存在下反应,并使所得酮肟甲基化 (VIII)与甲基化剂反应,并使所得的式(IX)的O-甲基酮肟与羟胺反应。 式(II)化合物是来自嗜球果伞素类的高活性杀真菌剂的中间体。
    • 3. 发明授权
    • Phenyl-methoxyimino-glyoxylic acid derivatives as pesticides
    • 苯甲氧基亚氨基 - 乙醛酸衍生物作为农药
    • US06372787B1
    • 2002-04-16
    • US09671421
    • 2000-09-27
    • Hugo ZieglerRené Zurflüh
    • Hugo ZieglerRené Zurflüh
    • C07C22940
    • C07C251/58A01N37/50C07C251/48C07C251/86C07C251/88C07C2601/02
    • Compounds of formula I wherein A is a group OCHR4 or N═CR4; Y is O or NH, R1 is C1-C6-alkyl; R2 is C1-C6-alkyl or C1-C6-alkyl substituted by 1 to 5 fluorine atoms; R3 is C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, C2-C6-alkenyl, C2-C6-alkenyloxy, C2-C6-alkinyl, C2-C6-alkinyloxy, C1-C6-alkoxycarbonyl, CN or halogen, aryl, hetaryl, heterocyclyl, aryloxy, hetaryloxy or heterocyclyloxy, whereby the above-mentioned groups, with the exception of CN and halogen, may be substituted by the same or different substituents; R4 is methyl, ethyl or cyclopropyl; R6 is hydrogen or methyl; have microbicidal, insecticidal and acaricidal activity, and may be used to control plant-pathogenic fungi, acarids and insects in agriculture and in the field of hygiene.
    • 式I的化合物,其中A是基团OCHR 4或N = CR 4; Y是O或NH,R 1是C 1 -C 6烷基; R 2是被1至5个氟原子取代的C 1 -C 6烷基或C 1 -C 6烷基; R 3是 C 1 -C 6 - 烷基,C 1 -C 6 - 烷氧基,C 3 -C 6 - 环烷基,C 3 -C 6 - 环烷氧基,C 2 -C 6 - 烯基,C 2 -C 6 - 烯氧基,C 2 -C 6 - C 6 - 烷氧基羰基,CN或卤素,芳基,杂芳基,杂环基,芳氧基,杂芳氧基或杂环氧基,其中除CN和卤素以外的上述基团可以被相同或不同的取代基取代; R4是甲基,乙基 或环丙基; R 6为氢或甲基;具有杀菌,杀虫和杀螨活性,可用于控制农业和卫生领域的植物病原真菌,螨虫和昆虫。
    • 4. 发明授权
    • Process for the preparation of pesticides
    • 农药制备工艺
    • US06646151B1
    • 2003-11-11
    • US09670147
    • 2000-09-26
    • Saleem FarooqStephan TrahHugo ZieglerRené Zurflüh
    • Saleem FarooqStephan TrahHugo ZieglerRené Zurflüh
    • C07C24904
    • C07C249/12C07C251/48C07C251/60
    • The invention relates to a process for the preparation of compounds of the formula or, if appropriate, a tautomer thereof, in each case in the free form or in salt form, in which A, X, Y, Z, R2, R3, R4, R5, R7, R9 and n are as defined in claim 1 and the C═N double bond marked with E has the E configuration, which comprises a1) reacting either a compound of the formula (II) mentioned above with a compound of the formula (III) mentioned above, in which X1 is a leaving group, or a2) a compound of the formula (IV) mentioned above, if appropriate in the presence of a base, with a compound of the formula (V) mentioned above, or b1) reacting a compound of the formula (VI) mentioned above with a compound of the formula R7—A—X2 (VII), in which X2 is a leaving group, and either further reacting the compound thus obtainable, of the formula (IV), for example according to method a2), or b2) reacting it with hydroxylamine or a salt thereof, if appropriate in the presence of a basic or acid catalyst, and further reacting the compound thus obtainable, of the formula (II), for example according to method a1), or c) reacting a compound of the formula (VIII), mentioned above with a C1-C6alkyl nitrite and further reacting the compound thus obtainable, of the formula (VI), for example according to method b), the E isomers of the compounds of the formulae (II), (IV) and (VI), a process for their preparation and their use for the preparation of compounds of the formula (I).
    • 本发明涉及一种制备式的化合物的方法,如果合适,其合适的是其互变异构体,其各自为游离形式或盐形式,其中A,X,Y,Z,R 2,R 3,R 4, R5,R7,R9和n如权利要求1中所定义,并且用E标记的C = N双键具有E构型,其包括a)使上述式(II)的化合物与式(II) III),其中X1是离去基团,ora2)如果合适的话,在碱的存在下,上述式(Ⅳ)的化合物与上述式(Ⅴ)的化合物相同,反应1)使 上述式(Ⅵ)化合物与式R7-A-X2(Ⅶ)化合物反应,其中X 2为离去基团,并进一步使由此得到的式(Ⅳ)化合物与 根据方法a2)的示例,orb2)如果合适,在碱性或酸性催化剂存在下,使其与羟胺或其盐反应,以及 进一步使由式(II)得到的化合物,例如按照方法a1)进行反应,或者使上述式(Ⅷ)化合物与亚硝酸C 1 -C 6烷基酯反应,并进一步使由此得到的化合物, 式(Ⅵ)化合物的方法,例如根据方法b),式(II),(Ⅳ)和(Ⅵ)化合物的E异构体,其制备方法及其制备方法 式(I)。
    • 10. 发明授权
    • O-benzyl oxime ether derivatives and their use as pesticides
    • US06211240B1
    • 2001-04-03
    • US08739388
    • 1996-10-29
    • René Zurflüh
    • René Zurflüh
    • A01N4342
    • C07D295/135A01N37/50A01N37/52C07C255/62C07C257/06C07C257/14C07C259/10C07C259/14C07C259/20C07C271/64C07C327/44C07C327/58C07C2601/02C07C2602/08C07C2602/10C07C2603/18C07D295/13C07F7/081
    • Compounds of the formula I in which Y is hydrogen, C1-C4alkyl, C1-C4alkoxy, OH, CN, NO2, Si(CH3)3, CF3 or halogen, Z is a group a) R1 is hydrogen, C1-C4alkyl, C2-C4alkenyl, C2-C4-alkynyl, C3-C6cycloalkyl, phenyl which is unsubstituted or at most trisubstituted by halogen, C1-C4alkyl, C1-C4alkoxy, C1-C4alkylthio, or benzyl which is unsubstituted or at most trisubstituted in the aromatic ring in the same manner; or is cyclopropylmethyl, C1-C4haloalkyl, C2-C5alkoxyalkyl, cyanomethyl, CO—R6, OH, NH2, C1-C4alkylamine or C1-C4alkoxycarbonyl-C1-C2alkyl; X is oxygen, sulfur or NR5; R2 is hydrogen, C1-C4alkyl, C2-C4alkenyl, C2-C4alkynyl, C3-C6cycloalkyl, C(O)R6, OH or C1-C4alkoxy, NH2 or C1-C4alkylamine; R5 is hydrogen, C1-C4alkyl, C2-C4alkenyl or C2-C4alkynyl; R6 is hydrogen, C114 C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C3-C6cycloalkyl, C1-C4alkoxycarbonyl or phenyl which is unsubstituted or at most trisubstituted; and in which R3 and R4 independently of one another are hydrogen, cyano, C1-C4alkyl, halo-C1-C4alkyl, C2-C4alkenyl, C2-C4alkynyl, C3-C6cycloalkyl, cyclopropylmethyl, C1-C4alkoxy, C2-C5alkoxyalkyl, C2-C4alkoxycarbonyl, C1-C4alkylthio, C2-C5-alkylthioalkyl; a ring having not more than 15 ring carbon atoms which can be polymembered and is unsubstituted or at most trisubstituted and has 0-3 hetero atoms N, O or S, it being possible for this ring to be bonded via an aliphatic bridge having not more than 4 carbon atoms and/or via either CO, oxygen or sulfur; or in which R3 and R4 together with the shared carbon atom are a ring or a polymembered ring system having not more than 15 ring carbon atoms which is unsubstituted or at most trisubstituted and has 0-3 hetero atoms N, O or S; are suitable for controlling and preventing attack by microorganisms of plants. They can be used in the form of commercially available formulated compositions.