clethodim | 99129-21-2

• 物质功能分类: 化学农药原药 - 除草剂 - 其他除草剂
• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: clethodim
• 英文别名: 2-{(E)-1-[(E)-3-chloroallyloxyimino]propyl}-5-[2-(ethylthio)propyl]-3-hydroxy-2-cyclohexen-1-one；(E,E)-2-[1-[[(3-chloro-2-propenyl)oxy]-imino]-propyl]-5-[2-(ethylthio)propyl]-3-hydroxy-2-cyclohexen-1-one；Clethodim；2-[(E)-N-[(E)-3-chloroprop-2-enoxy]-C-ethylcarbonimidoyl]-5-(2-ethylsulfanylpropyl)-3-hydroxycyclohex-2-en-1-one
• CAS: 99129-21-2
• 化学式: C₁₇H₂₆ClNO₃S
• 分子量: 359.917
• InChiKey: SILSDTWXNBZOGF-KUZBFYBWSA-N

物化性质

• 熔点：
  <25 °C
• 沸点：
  472.6±55.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少量，超声），乙酸乙酯（少量），甲醇（少量）
• 颜色/状态：
  Clear amber liquid
• 闪点：
  162 °F (72 °C) (Closed cup) /Select Max Herbicide/
• 蒸汽压力：
  2.66X10-9 mm Hg at 25 °C (est)
• 亨利常数：
  Henry's Law constant = 1.16X10-11 atm-cu m/mol at 25 °C (est)
• 稳定性/保质期：
  Unstable at extreme pH's, temperature and upon exposure to UV light. /Select Max Herbicide/

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  5

ADMET

代谢

一只哺乳期的山羊在苜蓿饲料中接受了（丙基-1-(14)C）-克草畏，剂量为每天每千克体重1.16毫克，分为三个等量的每日剂量，每个剂量为14.2毫克，连续三天，然后在第四天给予一个单独的剂量14.2毫克，总共10剂。一只母山羊作为对照。在最后一次给药后4小时宰杀了处理过的山羊。/ ... 收集了后肢和前肢肌肉、腹膜和皮下脂肪、肝脏、肾脏、心脏和血液，以允许代谢物的鉴定。主要的尿液代谢物是克草畏亚砜，占总尿液碳14的67%。其他尿液中放射性标记的成分被鉴定为克草畏（3-27%）和去甲基亚砜（12-18%）、S-甲基（7-13%）、亚胺亚砜（1.5-2.8%）、磺酰（1.5-2.2%）和5-羟基亚砜（0-3%）。在牛奶中，约一半的碳14可以被有机溶剂提取，并以克草畏、克草畏亚砜和克草畏去甲基亚砜的形式存在；另一半的碳14是水溶性的，被证明是（14）C-乳糖。在血液和组织中，最大可提取的放射性碳残留物占放射性标记的77-95%，被鉴定为克草畏和亚砜、去甲基亚砜、亚胺亚砜、磺酰和5-羟基磺酰。山羊的拟议代谢途径与大鼠的拟议代谢途径基本相同。

... A lactating goat received (propyl-1-(14)C)-clethodim / at 1.16 mg/kg bw per day in alfalfa diet, in three equal daily doses of 14.2 mg for three days and then a single dose of 14.2 mg on the fourth day, for a total of 10 doses. One female goat served as control. The treated goat was sacrificed 4 hrs after the final dose. / ... hind- and forequarter muscle, peritoneal and subcutaneous fat, liver, kidneys, heart and blood were collected to allow characterization of metabolites. The major urinary metabolite was clethodim sulfoxide, which accounted for 67% of the urinary radiocarbon. Other urinary radiolabelled components were identified as clethodim (3-27%) and demethyl sulfoxide (12-18%), S-methyl (7-13%), imine sulfoxide (1.5-2.8%), sulfone (1.5-2.2%) and 5-hydroxy sulfoxide (0-3%). In the milk, about half of the radiocarbon could be extracted into organic solvents and occurred in clethodim, clethodim sulfoxide and clethodim demethyl sulfoxide; the other half of the radiocarbon was water soluble and was shown to be (14)C-lactose. In blood and tissues, the maximal extractable radiocarbon residues accounted for 77-95% of the radiolabel and were identified as clethodim and the sulfoxide, demethyl sulfoxide, imine sulfoxide, sulfone and 5-hydroxy sulfone. The proposed metabolic pathway in goats was essentially the same as that proposed for rats.

来源:Hazardous Substances Data Bank (HSDB)

代谢

两组各八只白来航蛋鸡每天通过胶囊服用(cyclohexene-4,6-(14)C)-clethodim，剂量为2.1或51.3毫克/千克体重，连续五天。在最后一次给药后大约4小时宰杀蛋鸡，并收集组织进行分析。在组织和鸡蛋中鉴定出两种主要代谢物，clethodim磺酮和clethodim亚砜。clethodim磺酮占组织放射性标签水平的57%，而clethodim亚砜占10-31%。clethodim亚砜是蛋白(26-82%)和蛋黄(25-37%)中的主要代谢物；亲本clethodim在组织和鸡蛋中的检出量显著较少。鸡的代谢途径与在大鼠和山羊中观察到的不同，被认为是更简单的，因为在鸡中没有检测到亚胺、5-羟基或S-甲基类似物。

Two groups of eight white Leghorn laying hens were given daily doses of (cyclohexene-4,6-(14)C)-clethodim at 2.1 or 51.3 mg/kg bw per day by capsule for five consecutive days. The hens were sacrificed about 4 hrs after the final dose, and tissues were collected for analysis. Two major metabolites, clethodim sulfone and clethodim sulfoxide, were identified in tissues and eggs. Clethodim sulfone accounted for up to 57% of tissue levels of radiolabel, whereas clethodim sulfoxide accounted for 10-31%. Clethodim sulfoxide was the principal metabolite in egg white (26-82%) and yolk (25-37%); parent clethodim was detected in significantly smaller amounts in both tissues and eggs. The proposed metabolic pathway in chickens was different from and considered to be simpler than that observed in rats and goats, since none of the imine, 5-hydroxy or S-methyl analogues was detected in chickens.

来源:Hazardous Substances Data Bank (HSDB)

代谢

一组雄性大鼠（Crl:CD(SD)BR）单次口服给予450 mg/kg体重的放射性标记化合物，以确保有足够大量的标记代谢物。收集尿液和粪便，并分析原化合物及其代谢物。所有剂量组中雄性和雌性的代谢轮廓非常相似。确定了九种尿液代谢物并进行表征。主要代谢物是克草畏亚砜（占给药剂量的65-75%），还有少量的是亚胺亚砜（6-13%）、磺酰亚胺（1-3%）、5-羟基亚砜/磺酰亚胺（0.5-1.5%）和恶唑磺酰亚胺（0-5%）。主要的粪便代谢物，占放射性标记的1%以上，被确认为克草畏亚砜和亚胺亚砜。少量的（占给药剂量<1%）尿液和粪便代谢物是恶唑磺酰亚胺、去甲基亚砜和芳香磺酰亚胺。其他少量的粪便代谢物是克草畏磺酰亚胺、三酮亚砜和C-烯烃。原克草畏约占给药剂量的1%。

... A group of male rats /Crl:CD(SD)BR/ were given a single oral dose of 450 mg/kg bw radiolabeled compound to ensure a sufficiently large quantity of labeled metabolites. Urine and feces were collected and analyzed for the parent compound and its metabolites. The metabolic profiles of males and females in all dose groups were remarkably similar. Nine urinary metabolites were identified and characterized. The major metabolite was clethodim sulfoxide (representing 65-75% of the administered dose), and smaller amounts were found of the imine sulfoxide (6-13%), the sulfone (1-3%), the 5-hydroxy sulfoxide/sulfone (0.5-1.5%) and the oxazole sulfone (0-5%). The primary fecal metabolites, which accounted for more than 1% of the radiolabel, were identified as clethodim sulfoxide and the imine sulfoxide. Minor (present as < 1% of the dose) urinary and fecal metabolites were the oxazole sulfoxide, the demethyl sulfoxide and the aromatic sulfone. Other minor fecal metabolites were clethodim sulfone, the trione sulfoxide and c-olefins. Parent clethodim accounted for about 1% of the administered dose.

来源:Hazardous Substances Data Bank (HSDB)

代谢

拟除虫菊酯类农药的代谢途径在大鼠体内被提出...推测一旦拟除虫菊酯类农药被吸收，它可以通过以下途径进行代谢：被氧化成拟除虫菊酯亚砜（主要过程）；通过硫正离子中间体转化为S-甲基；在肟的N-O键处断裂生成亚胺；或者在5位上发生羟基化。

The proposed metabolic pathways for clethodim in rats ... is postulated that once clethodim has been absorbed it can be: oxidized to clethodim sulfoxide (dominant process); converted to the S-methyl via a sulfonium cation intermediate; cleaved at the oxime N-O bond to generate imine or hydroxylated at the 5 position.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 立即急救：确保已经进行了充分的中毒物质清洗。如果患者停止呼吸，立即开始人工呼吸，最好使用需求阀复苏器、气囊面罩装置或口袋面罩，按训练操作。如有必要，进行心肺复苏。立即用缓慢流动的水冲洗受污染的眼睛。不要催吐。如果患者呕吐，让患者身体前倾或置于左侧卧位（如果可能的话，头部向下）以保持呼吸道畅通，防止误吸。保持患者安静，维持正常体温。寻求医疗救助。 /毒物A和B/

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 基本治疗：建立专利气道（如有需要，使用口咽或鼻咽气道）。如有必要，进行吸痰。观察呼吸不足的迹象，如有需要，协助通气。通过非循环呼吸面罩以10至15升/分钟的速度给予氧气。监测肺水肿，如有必要，进行治疗……。监测休克，如有必要，进行治疗……。预防癫痫发作，如有必要，进行治疗……。对于眼睛污染，立即用水冲洗眼睛。在运输过程中，用0.9%的生理盐水（NS）连续冲洗每只眼睛……。不要使用催吐剂。对于摄入，如果患者能吞咽、有强烈的呕吐反射且不流口水，则用水冲洗口腔，并给予5毫升/千克，最多200毫升的水进行稀释……。在去污后，用干性无菌敷料覆盖皮肤烧伤……。/毒药A和B/

/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 高级治疗：对于无意识、严重肺水肿或严重呼吸困难的病人，考虑进行口咽或鼻咽气管插管以控制气道。使用气囊面罩装置的正压通气技术可能有益。考虑使用药物治疗肺水肿……。对于严重的支气管痉挛，考虑给予β激动剂，如沙丁胺醇……。监测心率和必要时治疗心律失常……。开始静脉输注D5W /SRP: "保持开放"，最小流量/。如果出现低血容量的迹象，使用0.9%的生理盐水（NS）或乳酸林格氏液。对于伴有低血容量迹象的低血压，谨慎给予液体。注意液体过载的迹象……。使用地西泮或劳拉西泮治疗癫痫……。使用丙美卡因氢氯化物协助眼部冲洗……。 /Poisons A and B/

/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

实验室动物：急性暴露/五只雌性Crl:CD (SD)BR大鼠每组接受5-羟基磺酰氯或技术级氯噻菌胺作为单一口服剂量，1.4 g/kg体重。没有观察到毒性临床体征，接受5-羟基磺酰氯处理的所有动物在给药后14天的观察期内存活。接受氯噻菌胺处理的五只大鼠均表现出明显的毒性迹象，包括流涎、活动减少、倒下、过度活跃、震颤、腹泻、脱水以及鼻、眼、口腔和肛门生殖器分泌物，且在给药后三天内全部死亡。

/LABORATORY ANIMALS: Acute Exposure/ Groups of five female Crl:CD (SD)BR rats received the 5-hydroxy sulfone of clethodim or technical-grade clethodim as a single oral dose of 1.4 g/kg bw. There were no clinical signs of toxicity, and all animals treated with the 5-hydroxy sulfone survived the 14-day observation period after dosing. All five rats treated with clethodim showed overt signs of toxicity, noted as salivation, decreased motor activity, collapse, hyperactivity, tremors, diarrhea, dehydration and nasal, ocular, oral and anogenital discharge, and all died within three days of dosing.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

实验室动物：急性暴露/五只雌性Crl:CD(SD)BR大鼠单次口服给予1.4克/千克体重的克草畏亚胺砜。一只动物在给药后4小时活动减少，第二天死亡。/亚胺砜/

/LABORATORY ANIMALS: Acute Exposure/ Five female Crl:CD(SD)BR rats were given a single oral dose of 1.4 g/kg bw of the imine sulfone of clethodim. One animal had decreased motor activity 4 hrs after dosing and was dead the next day. /imine sulfone/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

一只泌乳的山羊每天通过苜蓿饲料接受1.16毫克/千克体重的(丙基-1-(14)C)-克利索迪姆，分为三次等量的14.2毫克，连续三天，然后在第四天给予单一剂量的14.2毫克，共计10剂。一只母山羊作为对照组。在最后一次给药后4小时处死了处理过的山羊。克利索迪姆迅速被吸收：首次给药后第一小时内达到血液放射性碳浓度的高峰（0.273 ppm）。尿液回收的放射性标签的平均量代表给药量的56%，粪便中为34%。牛奶、血液和组织中发现的放射性标签总量少于给药量的1%...组织中含量为0.37%，血液中为0.22%。在肝脏和肾脏中检测到最高的残留组织浓度。

A single lactating goat received (propyl-1-(14)C)-clethodim at 1.16 mg/kg bw per day in alfalfa diet, in three equal daily doses of 14.2 mg for three days and then a single dose of 14.2 mg on the fourth day, for a total of 10 doses. One female goat served as control. The treated goat was sacrificed 4 hrs after the final dose. Clethodim was rapidly absorbed: the peak blood radiocarbon concentration (0.273 ppm) was achieved within the first hour after the initial dose. The mean amount of radiolabel recovered in the urine represented 56% of the administered dose and that in the feces, 34%. The total amount of radiolabel found in the milk, blood and tissues represented less than 1% of the amount administered. ... The tissues contained 0.37% and the blood, 0.22% of the dose. The highest residual tissue concentrations were detected in the liver and kidney.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

8-10只白来亨鸡一组，连续五天分别给予0、2.1或51.3毫克/千克体重的(cyclohexene-4,6-(14)C)-clethodim，并在最后一次给药后大约4小时处死。放射性分析显示，低剂量的78%和高剂量的85%的放射性物质通过粪便排出；低剂量的1.9%和高剂量的4.2%在组织中找到。放射性同位素在组织中的分布按浓度递减顺序为：消化道>肾脏>肝脏。在蛋中，低剂量的0.1%和高剂量的0.3%被发现；在蛋白中的水平最高，壳中次之，蛋黄中最低。

Groups of 8-10 white Leghorn laying hens were given (cyclohexene-4,6-(14)C)-clethodim at 0, 2.1 or 51.3 mg/kg bw per day for five consecutive days and were sacrificed about 4 hrs after the final treatment. Radioanalysis showed that 78% of the low dose and 85% of the high dose of administered radioactivity was excreted in the feces; 1.9% of the low dose and 4.2% of the high dose were found in the tissues. The radiolabel was distributed in the tissues in the following order of decreasing concentration: gastrointestinal tract > kidney > liver. In eggs, 0.1% of the low dose and 0.3% of the high dose were found; the levels were highest in egg whites, intermediate in shells and lowest in yolks.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

Crl:CD(SD)BR大鼠，不分性别，单次口服给予[丙基-1-(14)C]-clethodim剂量为4.4或468 mg/kg体重，或者每日给予未标记的测试物质4.5 mg/kg体重，连续14天，然后在单次放射性标记剂量4.8 mg/kg体重处理之前。消除是快速的：处理后48小时内排出了94-98%的给药剂量。主要排泄途径是尿液（87-93%），较小比例的放射性物质以粪便形式排出（9-17%）。以二氧化碳形式呼出的放射性物质的平均量占给药剂量的0.5-1%。尽管所有组的消除模式相似，但单次低剂量4.4 mg/kg体重处理的大鼠（40小时内消除98%）的消除速度比单次高剂量468 mg/kg体重处理的大鼠（50小时内消除98%）略快。对于连续低剂量给药的大鼠，无论雌雄，消除速率没有差异。治疗7天后，从器官和组织中回收的放射性标签总量不到给药剂量的1%。残留组织浓度最高的是肾上腺、肾脏和肝脏。当以给药剂量的比例表示时，组织分布中没有显著的剂量相关或性别特异性差异，也没有生物积累的证据。

Male and female Crl:CD(SD)BR rats were given single oral doses of [propyl-1-(14)C]-clethodim at 4.4 or 468 mg/kg bw or unlabelled test material at 4.5 mg/kg bw per day for 14 consecutive days before treatment with a single radiolabeled dose of 4.8 mg/kg bw. Elimination was rapid: 94-98% of the administered dose was excreted within 48 hrs after treatment. The principal route of excretion was the urine (87-93%), and a smaller percentage (9-17%) of the radioactivity was eliminated in the feces. The mean amount of radioactivity excreted in expired air as carbon dioxide represented 0.5-1% of the administered dose. Although the elimination patterns were similar in all groups, the rate of elimination was somewhat faster in animals that were administered the single low dose of 4.4 mg/kg bw (98% eliminated within 40 hrs) than in those given the single high dose of 468 mg/kg bw (98% within 50 hrs). No differences in elimination rate were seen for animals of either sex administered repeated low doses of clethodim. Seven days after treatment, the total amount of radiolabel recovered from organs and tissues was less than 1% of the administered dose. The highest residual tissue concentrations were found in the adrenals, kidney and liver. There were no significant dose-related or sex-specific differences in tissue distribution, when expressed as a proportion of the dose administered, and there was no evidence of bioaccumulation.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 安全说明：
  S22,S24/25
• WGK Germany：
  3
• 海关编码：
  2914700090
• 危险品运输编号：
  UN3082 (environmentally haz-ardous substances, liquid, n. o. s.)

制备方法与用途

简介

烯草酮（Clethodim）的中文商品名是收乐通、赛乐特。该除草剂最初由Kincade RT等在1987年布莱顿植保会议上报道其除草活性，由美国Chevron Chemical公司首先开发。烯草酮是一种环己烯酮类低毒除草剂，大鼠急性经口LD₅₀为1630 mg/kg（雄性）、1360 mg/kg（雌性），小鼠为2570 mg/kg（雄性）、2430 mg/kg（雌性）。

作用

主要适用于大豆、亚麻、烟草、西瓜等多种作物的农田除草，有效防除稗草等30余种禾本科杂草。该除草剂是内吸传导型茎叶处理剂，经叶片吸收后传导至分生组织和根部，破坏细胞分裂并抑制植物生长，导致植株在施药1～3周内褪绿坏死、枯萎死亡。烯草酮在土壤中的半衰期为3～26天，对后茬作物无影响。其作用机制与稀禾啶、精吡氟禾草灵、精喹禾灵等类似，均为乙酰辅酶A羧化酶（ACCase）抑制剂。

作用机理

烯草酮是一种ACCase抑制剂，为内吸传导型茎叶处理除草剂。经茎叶处理后，快速被叶片吸收并传导到分生组织，在敏感植物中抑制支链脂肪酸和黄酮类化合物的生物合成，破坏细胞分裂，导致植株生长延缓。施药1～3周后，植株褪绿坏死、枯萎死亡。

使用对象

烯草酮适用于大豆、油菜、烟草、棉花、花生、亚麻等阔叶田作物，可有效防除稗草、硬草、马唐、野燕麦、看麦娘、狗尾草、牛筋草、早熟禾等多种禾本科杂草。作为一种新型旱田苗后除草剂，烯草酮具有优良的选择性，能迅速被禾本科杂草茎叶吸收并传导至茎尖及分生组织，抑制其活性，破坏细胞分裂，最终导致杂草死亡。

毒性

大鼠急性经口LD₅₀为1360～1630 mg/kg，兔急性经皮LD₅₀>5000 mg/kg，大鼠急性吸入LC₅₀>3.9 mg/L（42小时）。对眼睛和皮肤有轻微刺激性。小鼠经口无作用剂量每天为625 mg/kg体重，动物试验未见致畸、致癌、致突变作用。对鱼类、鸟类低毒。虹鳟鱼LC₅₀为67 mg/L （96小时），蓝鳃鱼LC₅₀>120 mg/L，水蚤LC₅₀>120 mg/L（48小时）。鹌鹑LD₅₀>2000 mg/kg，对蜜蜂安全。

生产方法

在氢氧化钠存在下，由相应的烯酮与丙二酸二乙酰缩合、环合，制得5-烷基环己二酮-3-羧酸酯。再经水解、脱羧后，与丙酰氯反应生成3-丙酰氧基-5-烷基环己烯酮。将产物溶于二氯甲烷中，在三氯化铝存在下进行异构化反应，生成2-丙酰基-3-羟基-5-烷基环己酮。最后与H₂NOCH₂CH=CHCl反应，合成烯草酮。

反应信息

• 作为反应物：
  描述：

  clethodim 以 水 为溶剂， 生成
  参考文献：
  名称：

  水和有机溶剂中除草剂草胺定的互变异构和EZ平衡：核磁共振和理论研究

  摘要：

  除草剂杀虫菊酯可以不同的互变异构形式存在，也可以作为E - Z异构体存在。以前的工作已经对互变异构问题进行了一些探讨，并始终指出E形式是唯一的一种稳定形式。在这项工作中，通过溶液中的质子核磁共振（1 H NMR），碳13核磁共振（13 C NMR）和相关光谱（COSY）实验研究了来昔定的互变异构平衡。四种溶剂（CDCl 3，丙酮d 6，二甲基亚砜（DMSO）d 6和D 2O）。已经确定了主要的互变异构物种，并且已经从头孢噻肟的氯烯丙基的氢的积分中计算出了平衡常数。E-酮烯胺是CDCl 3中唯一可检测的互变异构体。在丙酮d 6和DMSO d 6中观察到了E-酮烯胺和E-二酮烯胺互变异构体的混合物（比例分别为8:92和53:47）。在水中，最丰富的中性互变异构体是E-酮烯胺，E-二酮烯胺和Z-酮烯胺（互变异构比为66:20:14）。标识E和Z据报道互变异构体。当考虑特定的乙二胺-溶剂氢键时，热

  DOI：

  10.1002/poc.4108
• 作为产物：
  描述：

  2,4-庚二烯-6-酮 在 盐酸 、 4-二甲氨基吡啶 、 sodium methylate 、 溶剂黄146 、 三乙胺 、 丙二酸二甲酯 作用下， 以 水 、 甲苯 、 Petroleum ether 为溶剂， 反应 29.25h， 生成 clethodim
  参考文献：
  名称：

  一种合成烯草酮的方法

  摘要：

  本发明提出了一种合成烯草酮的方法，包括3,5‑庚二烯‑2‑酮(式II)与乙硫醇进行亲核加成制得烯草酮中间体6‑乙硫基‑3‑庚烯‑2‑酮(式III)；式III再与丙二酸二甲酯、丙酰氯反应经中间体IV制得(±)‑3‑[丙酰氧基]‑5‑[2‑(乙硫基)丙基]‑6‑[甲氧甲酰基]环己‑2‑烯酮(式V)；式V再经过重排、水解、脱羧反应制得(±)‑2‑[丙酰基]‑3‑[羟基]‑5‑[2‑(乙硫基)丙基]环己‑2‑烯酮(式VIII)；式VIII再与氯代烯丙氧胺反应制得烯草酮(式I)，本发明采用中间体3,5‑庚二烯‑2‑酮(式II)制备烯草酮的方法为首次提出，通过本方法制备的烯草酮(式I)总体收率高，产品质量好，并且本方法生产成本低，环境污染小，适合大规模生产。

  公开号：

  CN107162945A

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。