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    • 4. 发明授权
    • Process for the preparation of a triazolinone herbicide
    • 制备三唑啉酮除草剂的方法
    • US06268506B1
    • 2001-07-31
    • US09688406
    • 2000-10-16
    • Gerard A. CrispinoJaidev S. Goudar
    • Gerard A. CrispinoJaidev S. Goudar
    • C07D24912
    • C07D249/12
    • 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.
    • 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。
    • 6. 发明授权
    • Process for the preparation of a triazolinone herbicide
    • 制备三唑啉酮除草剂的方法
    • US6077959A
    • 2000-06-20
    • US172157
    • 1998-10-14
    • Gerard A. CrispinoJaidev S. Goudar
    • Gerard A. CrispinoJaidev S. Goudar
    • C07D249/12
    • C07D249/12
    • 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.
    • 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。
    • 7. 发明授权
    • Method of preparing aryl triazolinones with trialkyl orthoacetates
    • 用三烷基原乙酸酯制备芳基三唑啉酮的方法
    • US5543541A
    • 1996-08-06
    • US416560
    • 1995-04-04
    • Jaidev S. Goudar
    • Jaidev S. Goudar
    • C07D249/12C07C243/22
    • C07D249/12
    • 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.
    • 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。
    • 9. 发明授权
    • Process to prepare aryltriazolinones and novel intermediates thereto
    • 制备芳基三唑啉酮及其新型中间体的方法
    • US06992221B2
    • 2006-01-31
    • US10341012
    • 2003-01-13
    • Jaidev S. Goudar
    • Jaidev S. Goudar
    • C07C243/18C07C243/22
    • C07C257/22C07D249/12
    • 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.
    • 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。
    • 10. 发明授权
    • Process for the preparation of a triazolinone herbicide
    • 制备三唑啉酮除草剂的方法
    • US06194583B1
    • 2001-02-27
    • US09525394
    • 2000-03-15
    • Gerard A. CrispinoJaidev S. Goudar
    • Gerard A. CrispinoJaidev S. Goudar
    • C07D24912
    • C07D249/12
    • 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.
    • 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。