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    • 10. 发明授权
    • Process for preparing substituted N-carbamoyl-Tetrazolinones
    • 取代的N-氨基甲酰基 - 四唑啉酮的制备方法
    • US5686392A
    • 1997-11-11
    • US595088
    • 1996-02-01
    • Uwe StelzerWolfgang GauKarl-Julius Reubke
    • Uwe StelzerWolfgang GauKarl-Julius Reubke
    • A01N47/38B01J31/02C07D257/04
    • C07D257/04
    • The herbicidally active substituted N-carbamoyl-tetrazolinones of the formula (I) ##STR1## in which R.sup.1 represents, inter alia, an (optionally substituted) phenyl radical, R.sup.2 represents, inter alia, an alkyl radical, and R.sup.3 represents, inter alia, a cycloalkyl radical, are obtained in very good yields and at high purity--i.e. free from the isomeric O-carbamoyloxytetrazoles (Ia)--by reacting tetrazolinones of the formula (II) with carbamoyl halides of the formula (III) (X=halogen) ##STR2## in the presence of an acid acceptor and in the presence of a diluent, at temperatures of between 0.degree. C. and 200.degree. C., and either isomerizing the O-carbamoylation product of the formula (Ia), which is formed under these circumstances as a byproduct, into the desired product of the formula (I) by heating, or else converting it by hydrolysis or alcoholysis into water-soluble, and thus readily separable, components (variable (a)). Three variants (b), (c) and (d) which are closely related to this process (a) are also described: Process variant (b) proceeds in analogy with (a) but via the (novel, isolated) metal salts (IIa) of the tetrazolinones (II). In variant (c), the isomer (Ia) is isomerized thermally, either in pure isolated form or mixed with (I), while, in variant (d), the (Ia) isomer is removed from (I)/(Ia) mixtures by means of hydrolysis or alcoholysis. The novel intermediates (Ia) and (IIa) also belong, as such, to the subject-matter of the invention.
    • 式(I)的除草活性的取代的N-氨基甲酰基 - 四唑啉酮,其中R 1特别是(任选取代的)苯基,R 2特别包括, 烷基,和R3代表环烷基,以非常好的产率和高纯度获得,即 通过使式(II)的四唑啉酮与式(III)的氨基甲酰基卤化物(X =卤素)在酸受体的存在下反应而不存在异构O-氨基甲酰氧基四唑(Ia) 稀释剂,在0℃至200℃的温度下,将在这些情况下作为副产物形成的式(Ia)的O-氨基甲酰基化产物异构化为所需的式(I ),或者通过水解或醇解将其转化为水溶性的,因此易于分离的组分(可变(a))。 还描述了与该方法(a)密切相关的三个变体(b),(c)和(d):方法变体(b)类似于(a)进行,但通过(新颖的,分离的)金属盐 IIa)四唑啉酮(II)。 在变体(c)中,异构体(Ia)以纯分离形式或与(I)混合而异构化,而在变体(d)中,(Ia)异构体从(I)/(Ia) 混合物通过水解或醇解。 新颖的中间体(Ia)和(IIa)也属于本发明的主题。