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    Process for the preparation of a triazolinone herbicide
    2.
    发明授权
    Process for the preparation of a triazolinone herbicide 失效
    制备三唑啉酮除草剂的方法

    公开(公告)号：US06268506B1

    公开(公告)日：2001-07-31

    申请号：US09688406

    申请日：2000-10-16

    申请人： Gerard A. Crispino ,  Jaidev S. Goudar

    发明人： Gerard A. Crispino ,  Jaidev S. Goudar

    IPC分类号： C07D24912

    CPC分类号： C07D249/12

    摘要： A process for preparing an alkyl &agr;-2-chloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl]-2,4-substituted-benzene-propanoate herbicide, by reacting an alkyl &agr;-acetyl-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl]-2,4-disubstituted-benzene-propanoate, Intermediate D, first with sodium hypochlorite, then with a base, and recovering the herbicide. Intermediate D is prepared by reacting a 1-(2,4-disubstituted-5-halophenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazole, Intermediate B, with an alkyl alkanoate in the presence of a palladium catalyst and a tertiary amine. Intermediate B is prepared by reacting a 1-(2,4-disubstituted-phenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazole with a halogenating agent in the presence of an acid. The 2,4-substituents are independently selected from halo, alkyl, cycloalkyl, alkoxy, nitro, or hetercyclyl.

    摘要翻译： 制备α-2-氯-5- [4-（二氟甲基）-4,5-二氢-3-甲基-5-氧代-1H-1,2,4-三唑-1-基] - 通过α-烷基α-乙酰基-5- [4-（二氟甲基）-4,5-二氢-3-甲基-5-氧代-1H-1,2,4-三唑并[ 三唑-1-基] -2,4-二取代 - 苯 - 丙酸酯，中间体D，首先用次氯酸钠，然后与碱反应，并回收除草剂。 中间体D通过使1-（2,4-二取代-5-卤代苯基）-4-二氟甲基-4,5-二氢-3-甲基-5-氧代-1H-1,2,4-三唑，中间体 B与烷基链烷酸酯在钯催化剂和叔胺的存在下反应。 中间体B通过使1-（2,4-二取代 - 苯基）-4-二氟甲基-4,5-二氢-3-甲基-5-氧代-1H-1,2,4-三唑与卤化剂 在酸的存在下。 2,4-取代基独立地选自卤素，烷基，环烷基，烷氧基，硝基或杂环基。

    Process for the preparation of a triazolinone herbicide
    4.
    发明授权
    Process for the preparation of a triazolinone herbicide 失效
    制备三唑啉酮除草剂的方法

    公开(公告)号：US6077959A

    公开(公告)日：2000-06-20

    申请号：US172157

    申请日：1998-10-14

    申请人： Gerard A. Crispino ,  Jaidev S. Goudar

    发明人： Gerard A. Crispino ,  Jaidev S. Goudar

    IPC分类号： C07D249/12

    CPC分类号： C07D249/12

    摘要： A process for preparing an alkyl .alpha.-2-chloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl]-2,4-substituted-benzene-propanoate herbicide, by reacting an alkyl .alpha.-acetyl-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl]-2,4-disubstituted-benzene-propanoate, Intermediate D, first with sodium hypochlorite, then with a base, and recovering the herbicide. Intermediate D is prepared by reacting a 1-(2, 4-disubstituted-5-halophenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazole, Intermediate B, with an alkyl alkanoate in the presence of a palladium catalyst and a tertiary amine. Intermediate B is prepared by reacting a 1-(2,4-disubstituted-phenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazole with a halogenating agent in the presence of an acid. The 2,4-substituents are independently selected from halo, alkyl, cycloalkyl, alkoxy, nitro, or hetercyclyl.

    摘要翻译： 制备α-2-氯-5- [4-（二氟甲基）-4,5-二氢-3-甲基-5-氧代-1H-1,2,4-三唑-1-基] - 通过使α-乙酰基-5- [4-（二氟甲基）-4,5-二氢-3-甲基-5-氧代-1H-1,2,4-苯并二氮杂- 三唑-1-基] -2,4-二取代 - 苯 - 丙酸酯，中间体D，首先用次氯酸钠，然后与碱反应，并回收除草剂。 中间体D通过1-（2,4-二取代-5-卤代苯基）-4-二氟甲基-4,5-二氢-3-甲基-5-氧代-1H-1,2,4-三唑，中间体 B与烷基链烷酸酯在钯催化剂和叔胺的存在下反应。 中间体B通过使1-（2,4-二取代 - 苯基）-4-二氟甲基-4,5-二氢-3-甲基-5-氧代-1H-1,2,4-三唑与卤化剂 在酸的存在下。 2,4-取代基独立地选自卤素，烷基，环烷基，烷氧基，硝基或杂环基。

    Method of preparing aryl triazolinones with trialkyl orthoacetates
    6.
    发明授权
    Method of preparing aryl triazolinones with trialkyl orthoacetates 失效
    用三烷基原乙酸酯制备芳基三唑啉酮的方法

    公开(公告)号：US5543541A

    公开(公告)日：1996-08-06

    申请号：US416560

    申请日：1995-04-04

    申请人： Jaidev S. Goudar

    发明人： Jaidev S. Goudar

    IPC分类号： C07D249/12 ,  C07C243/22

    CPC分类号： C07D249/12

    摘要： A method for preparing an alkoxyethylidene-substituted aryl hydrazine having the formula ##STR1## and thereafter cyclizing the same with a cyanate salt under mildly acidic conditions in the presence of an organic solvent, optionally in the presence of a cyclization-aiding amount of water, to form an aryl triazolinone of the formula ##STR2## wherein X is independently hydrogen, halogen, lower alkyl, lower alkoxy, nitro, hydroxy, --NHSO.sub.2 R.sup.1, --NR.sup.1 SO.sub.2 R.sup.1, or --N(SO.sub.2 R.sup.1).sub.2, where R.sup.1 is lower alkyl; R is lower alkyl, and each R is the same; and n is an integer of from 1-3, which triazolinones am useful as intermediates for preparing herbicides.

    摘要翻译： 制备具有式（B）的烷氧基​​亚乙基取代的芳基肼的方法，然后在有机溶剂的存在下，在温和的酸性条件下，在任选地存在环化助剂量的情况下，用氰酸盐将其环化 的水，以形成下式的芳基三唑啉酮：其中X独立地为氢，卤素，低级烷基，低级烷氧基，硝基，羟基，-NHSO 2 R 1，-NR 1 SO 2 R 1或-N（SO 2 R 1）2，其中 R1是低级烷基; R是低级烷基，每个R相同; 并且n是1-3的整数，其中三唑啉酮可用作制备除草剂的中间体。

    Process to prepare aryltriazolinones and novel intermediates thereto
    8.
    发明授权
    Process to prepare aryltriazolinones and novel intermediates thereto 有权
    制备芳基三唑啉酮及其新型中间体的方法

    公开(公告)号：US06992221B2

    公开(公告)日：2006-01-31

    申请号：US10341012

    申请日：2003-01-13

    申请人： Jaidev S. Goudar

    发明人： Jaidev S. Goudar

    IPC分类号： C07C243/18 ,  C07C243/22

    CPC分类号： C07C257/22 ,  C07D249/12

    摘要： A process is described for preparing 1-aryltriazolinones of formula I useful in the production of commercial herbicides: by (i) carbonylating an amidrazone of formula (A) with one or more carbonylating agent, or by (ii) condensing a hydrazonoyl derivative of formula (A) with one or more ring-forming agent, wherein formula (A) is where W, X, Y, Z, and R1 are fully described herein. Preferred are those where W is halogen or —NHR where R is hydrogen or haloalkyl; X and Y are independently selected from hydrogen, chloro, or fluoro; Z is hydrogen, bromo, iodo, nitro, amino, or methylsulfonylamino; and R1 is methyl. Certain compounds of formula (A) are novel compositions of matter. The process as described herein has utility in providing compounds of formula I in unexpectedly high yield and purity.

    摘要翻译： 描述了用于制备商业除草剂的式I的1-芳基三唑啉酮的方法：通过（i）用一种或多种羰基化剂羰基化式（A）的氨基腙，或通过（ii）将式 （A）与一种或多种成环剂，其中式（A）是本文完整描述的W，X，Y，Z和R 1。 其中W是卤素或-NHR，其中R是氢或卤代烷基; X和Y独立地选自氢，氯或氟; Z是氢，溴，碘，硝基，氨基或甲基磺酰基氨基; R 1是甲基。 某些式（A）化合物是物质的新型组合物。 本文所述的方法可用于以令人满意的高产率和纯度提供式I化合物。

    Process for the preparation of a triazolinone herbicide
    9.
    发明授权
    Process for the preparation of a triazolinone herbicide 失效
    制备三唑啉酮除草剂的方法

    公开(公告)号：US06194583B1

    公开(公告)日：2001-02-27

    申请号：US09525394

    申请日：2000-03-15

    申请人： Gerard A. Crispino ,  Jaidev S. Goudar

    发明人： Gerard A. Crispino ,  Jaidev S. Goudar

    IPC分类号： C07D24912

    CPC分类号： C07D249/12

    摘要： A process for preparing an alkyl &agr;-2-chloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl]-2,4-substituted-benzene-propanoate herbicide, by reacting an alkyl &agr;-acetyl-5-[4-(difluoromethyl)4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl]-2,4-disubstituted-benzene-propanoate, Intermediate D, first with sodium hypochlorite, then with a base, and recovering the herbicide. Intermediate D is prepared by reacting a 1-(2, 4-disubstituted-5-halophenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazole, Intermediate B, with an alkyl alkanoate in the presence of a palladium catalyst and a tertiary amine. Intermediate B is prepared by reacting a 1-(2,4-disubstituted-phenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazole with a halogenating agent in the presence of an acid. The 2,4-substituents are independently selected from halo, alkyl, cycloalkyl, alkoxy, nitro, or hetercyclyl.

    摘要翻译： 制备α-2-氯-5- [4-（二氟甲基）-4,5-二氢-3-甲基-5-氧代-1H-1,2,4-三唑-1-基] - 通过α-乙酰基-5- [4-（二氟甲基）-4,5-二氢-3-甲基-5-氧代-1H-1,2,4-三唑的烷基酯的制备将2,4-取代的苯丙酸酯除草剂 -1-基] -2,4-二取代 - 苯 - 丙酸酯，中间体D，首先用次氯酸钠，然后与碱反应，并回收除草剂。 中间体D通过1-（2,4-二取代-5-卤代苯基）-4-二氟甲基-4,5-二氢-3-甲基-5-氧代-1H-1,2,4-三唑，中间体 B与烷基链烷酸酯在钯催化剂和叔胺的存在下反应。 中间体B通过使1-（2,4-二取代 - 苯基）-4-二氟甲基-4,5-二氢-3-甲基-5-氧代-1H-1,2,4-三唑与卤化剂 在酸的存在下。 2,4-取代基独立地选自卤素，烷基，环烷基，烷氧基，硝基或杂环基。