氟吡磺隆 | 412928-75-7

• 物质功能分类: 化学农药原药 - 除草剂 - 磺酰脲类除草剂
• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 氟吡磺隆
• 英文名称: flucetosulfuron
• 英文别名: N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]-carbonyl]-2-[2-fluoro-1-(methoxymethylcarbonyloxy)propyl]-3-pyridinesulfonamide；[1-[3-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]pyridin-2-yl]-2-fluoropropyl] 2-methoxyacetate
• CAS: 412928-75-7
• 化学式: C₁₈H₂₂FN₅O₈S
• 分子量: 487.466
• InChiKey: FICWGWVVIRLNRB-UHFFFAOYSA-N

物化性质

• 熔点：
  178–182°C
• 密度：
  1.417±0.06 g/cm3(Predicted)
• 溶解度：
  Solubility in organic solvents (g/l at 20 °C) Acetone 22.9 Ethyl acetate 11.7 Dichloromethane 113.0 Dimethylformamide 265.0 Dimethylsulfoxide 211.7 n‐Hexane 0.006 Methanol 3.8

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  176
• 氢给体数：
  2
• 氢受体数：
  12

制备方法与用途

概述

氟吡磺隆是一种磺酰脲类除草剂，作为乙酰乳酸合成酶（ALS）抑制剂，主要用于水稻田的土壤或茎叶处理。它通过被植物的根、茎和叶吸收，在体内抑制乙酰乳酸合成酶，从而阻碍支链氨基酸如缬氨酸、亮氨酸、异亮氨酸的生物合成，破坏蛋白质的合成，并干扰DNA的合成及细胞分裂与生长，最终导致植物死亡。氟吡磺隆对禾本科杂草、阔叶杂草和莎草科杂草均有较好的防除效果，尤其对稗草、扁秆藨草、野慈姑、丁香蓼、莎草等的防效可达90%左右；但在实际使用中，对双穗雀稗、千金子和眼子菜等防除效果较差。

毒性

氟吡磺隆属于磺酰胺类除草剂，同样通过抑制乙酰乳酸合成酶（ALS），阻止支链氨基酸如缬氨酸、异亮氨酸、亮氨酸的生物合成，最终破坏蛋白质的合成，并干扰DNA的合成及细胞分裂与生长。该除草剂可以通过植物的根、茎和叶吸收，其叶片传输速度比草甘膦更快。药害症状包括生长停止、叶片失绿以及顶端分生组织死亡，植株通常在2-3周后死亡。

反应信息

• 作为反应物：
  描述：

  氟吡磺隆 在 sodium hydroxide 作用下， 以 乙腈 为溶剂， 以89%的产率得到threo-N-(4,6-dimethoxypyrimidin-2-ylcarbamoyl)-2-(2-fluoro-1-hydroxypropyl)pyridine-3-sulfonamide
  参考文献：
  名称：

  In Vitro Metabolism of Flucetosulfuron by Human Liver Microsomes

  摘要：

  To investigate herbicide metabolism, human liver microsomes were incubated with threo- and erythro-isomers of flucetosulfuron. Each isomer produced one metabolite; the metabolites were unambiguously identified as enzymatic hydrolysis products by using liquid chromatography-tandem mass spectrometry (LC-MS/MS). These metabolites were synthesized, producing white solids characterized using LC-MS/MS and nuclear magnetic resonance spectroscopy (H-1 and C-13). Using specific esterase inhibitors and activators, carboxylesterases and cholinesterases were demonstrated to be involved in flucetosulfuron metabolism. Under optimized metabolic conditions, the kinetic parameters for metabolite formation from threo-flucetosulfuron and erythro-flucetosulfuron were: V-max, 151.41 and 134.38 nmol/min/mg protein, respectively; K-m, 2957.37 and 2798.53 mu M, respectively; and CLint, 51.20 and 48.02 mu L/min/mg microsomes respectively. No significant kinetic differences were observed between the two isomers. These results indicated that the primary metabolic pathway for both flucetosulfuron isomers in human liver microsomes involves hydrolysis, catalyzed by carboxylesterase and cholinesterase.

  DOI：

  10.1021/jf4048836
• 作为产物：
  描述：

  N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]-carbonyl]-2-[2-fluoro-1-(methoxymethylcarbonyloxy)propyl]-3-pyridinesulfonamide 在 Capcell pak C₁₈ UG₁₂₀ column 作用下， 以 乙腈 为溶剂， 反应 1.5h， 生成 氟吡磺隆
  参考文献：
  名称：

  In Vitro Metabolism of Flucetosulfuron by Human Liver Microsomes

  摘要：

  To investigate herbicide metabolism, human liver microsomes were incubated with threo- and erythro-isomers of flucetosulfuron. Each isomer produced one metabolite; the metabolites were unambiguously identified as enzymatic hydrolysis products by using liquid chromatography-tandem mass spectrometry (LC-MS/MS). These metabolites were synthesized, producing white solids characterized using LC-MS/MS and nuclear magnetic resonance spectroscopy (H-1 and C-13). Using specific esterase inhibitors and activators, carboxylesterases and cholinesterases were demonstrated to be involved in flucetosulfuron metabolism. Under optimized metabolic conditions, the kinetic parameters for metabolite formation from threo-flucetosulfuron and erythro-flucetosulfuron were: V-max, 151.41 and 134.38 nmol/min/mg protein, respectively; K-m, 2957.37 and 2798.53 mu M, respectively; and CLint, 51.20 and 48.02 mu L/min/mg microsomes respectively. No significant kinetic differences were observed between the two isomers. These results indicated that the primary metabolic pathway for both flucetosulfuron isomers in human liver microsomes involves hydrolysis, catalyzed by carboxylesterase and cholinesterase.

  DOI：

  10.1021/jf4048836

文献信息

• [EN] ACC INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE L'ACC ET UTILISATIONS ASSOCIÉES
  申请人：GILEAD APOLLO LLC

  公开号：WO2017075056A1

  公开（公告）日：2017-05-04

  The present invention provides compounds I and II useful as inhibitors of Acetyl CoA Carboxylase (ACC), compositions thereof, and methods of using the same.

  本发明提供了化合物I和II，这些化合物可用作乙酰辅酶A羧化酶（ACC）的抑制剂，以及它们的组合物和使用方法。
• [EN] 3-[(HYDRAZONO)METHYL]-N-(TETRAZOL-5-YL)-BENZAMIDE AND 3-[(HYDRAZONO)METHYL]-N-(1,3,4-OXADIAZOL-2-YL)-BENZAMIDE DERIVATIVES AS HERBICIDES<br/>[FR] DÉRIVÉS DE 3-[(HYDRAZONO))MÉTHYL]-N-(TÉTRAZOL-5-YL)-BENZAMIDE ET DE 3-[(HYDRAZONO)MÉTHYL]-N-(1,3,4-OXADIAZOL-2-YL)-BENZAMIDE UTILISÉS EN TANT QU'HERBICIDES
  申请人：SYNGENTA CROP PROTECTION AG

  公开号：WO2021013969A1

  公开（公告）日：2021-01-28

  The present invention related to compounds of Formula (I): or an agronomically acceptable salt thereof, wherein Q, R2, R3, R4, R5 and R6 are as described herein. The invention further relates to compositions comprising said compounds, to methods of controlling weeds using said compositions, and to the use of compounds of Formula (I) as a herbicide.

  本发明涉及以下式（I）的化合物或其农业上可接受的盐，其中Q、R2、R3、R4、R5和R6如本文所述。该发明还涉及包含所述化合物的组合物，使用这些组合物控制杂草的方法，以及将式（I）的化合物用作除草剂的用途。
• [EN] INSECTICIDAL TRIAZINONE DERIVATIVES<br/>[FR] DÉRIVÉS DE TRIAZINONE INSECTICIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2013079350A1

  公开（公告）日：2013-06-06

  Compounds of the formula (I) or (I'), wherein the substituents are as defined in claim 1, are useful as pesticides.

  式(I)或(I')的化合物，其中取代基如权利要求1所定义的那样，可用作杀虫剂。
• [EN] HERBICIDALLY ACTIVE HETEROARYL-S?BSTIT?TED CYCLIC DIONES OR DERIVATIVES THEREOF<br/>[FR] DIONES CYCLIQUES SUBSTITUÉES PAR HÉTÉROARYLE À ACTIVITÉ HERBICIDE OU DÉRIVÉS DE CELLES-CI
  申请人：SYNGENTA LTD

  公开号：WO2011012862A1

  公开（公告）日：2011-02-03

  The invention relates to a compound of formula (I), which is suitable for use as a herbicide wherein G is hydrogen or an agriculturally acceptable metal, sulfonium, ammonium or latentiating group; Q is a unsubstituted or substituted C3-C8 saturated or mono-unsaturated heterocyclyl containing at least one heteroatom selected from O, N and S, or Q is heteroaryl or substituted heteroaryl; m is 1, 2 or 3; and Het is an optionally substituted monocyclic or bicyclic heteroaromatic ring; and wherein the compound is optionally an agronomically acceptable salt thereof.

  该发明涉及一种化合物，其化学式为(I)，适用作为除草剂，其中G为氢或农业可接受的金属、磺酸盐、铵盐或潜伏基团；Q为未取代或取代的含有至少一个来自O、N和S的杂原子的饱和或单不饱和的C3-C8杂环烷基，或Q为杂芳基或取代的杂芳基；m为1、2或3；Het为可选择地取代的单环或双环杂芳环；且该化合物可选择地为其农学上可接受的盐。
• TRIAZOLE ACC INHIBITORS AND USES THEREOF
  申请人：Gilead Apollo, LLC

  公开号：US20170166584A1

  公开（公告）日：2017-06-15

  The present invention provides triazole compounds useful as inhibitors of Acetyl CoA Carboxylase (ACC), compositions thereof, and methods of using the same.

  本发明提供了三唑化合物，可用作乙酰辅酶A羧化酶（ACC）的抑制剂，以及其组合物和使用方法。