二异丙基硫代氨基甲酸S-[(E)-2,3-二氯烯丙基]酯 | 17708-58-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代羰基化合物
• 中文名称: 二异丙基硫代氨基甲酸S-[(E)-2,3-二氯烯丙基]酯
• 英文名称: trans-2,3-dichloroallyl-diisopropylthiolcarbamate
• 英文别名: trans-Diallate；S-[(E)-2,3-dichloroprop-2-enyl] N,N-di(propan-2-yl)carbamothioate
• CAS: 17708-58-6
• 化学式: C₁₀H₁₇Cl₂NOS
• 分子量: 270.223
• InChiKey: SPANOECCGNXGNR-WEVVVXLNSA-N

物化性质

• 沸点：
  306.0±52.0 °C(Predicted)
• 密度：
  1.180±0.06 g/cm3(Predicted)
• 物理描述：
  Used as an herbicide.
• 颜色/状态：
  BROWN LIQUID
• 熔点：
  25.0 °C
• 闪点：
  96 C deg (open cup); 77 °C (closed cup)
• 溶解度：
  SOL IN WATER 14 PPM @ 25 °C
• 蒸汽压力：
  1.5X10-4 MM HG @ 25 °C
• 稳定性/保质期：
  INDEFINITELY STABLE; NOT SENSITIVE TO LIGHT OR HEAT
• 分解：
  DECOMP AT TEMP GREATER THAN 200 °C
• 腐蚀性：
  NONCORROSIVE
• 保留指数：
  1693.2

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  2

ADMET

代谢

鼠标肝微粒体代谢顺式和反式-(14)C=O-二醇酸盐，在NADPH依赖反应中，主要产生(14)CO2，在没有谷胱甘肽（GSH）的情况下，以及在GSH存在时产生(14)CO2和S-(二异丙基羧基)-GSH。给予任一异构体的老鼠除了排出(14)CO2（20%）外，还排出S-二异丙基羧基衍生物的巯基尿酸（62%）、半胱氨酸（7%）和巯基乙酸（1.5%）。这条途径似乎涉及亚磺氧化，亚磺酸盐与GSH和非酶促反应以及巯基尿酸的形成。

MOUSE HEPATIC MICROSOMES METABOLIZE CIS- & TRANS-(14)C=O-DIALLATE IN NADPH-DEPENDENT REACTION, YIELDING PRIMARILY (14)CO2 IN ABSENCE OF GLUTATHIONE (GSH) & (14)CO2 & S-(DIISOPROPYLCARBAMOYL)-GSH IN PRESENCE OF GSH. RATS ADMIN EITHER ISOMER EXCRETE S-DIISOPROPYLCARBAMOYL DERIV OF MERCAPTURIC ACID (62%), CYSTEINE (7%) & MERCAPTOACETIC ACID (1.5%) IN ADDN TO (14)CO2 (20%). PATHWAY APPEARS TO INVOLVE SULFOXIDATION, NONENZYMATIC REACTION OF SULFOXIDE WITH GSH & MERCAPTURIC ACID FORMATION.

来源:Hazardous Substances Data Bank (HSDB)

代谢

以口服方式处理多种促突变剂和含卤代烯基或卤代烷基取代基的致癌物的老鼠，会从敌草快中排出少量尿液中的2-卤代丙烯酸，例如2-氯丙烯酸和2,3-二氯丙烯酸。

RATS TREATED ORALLY WITH SEVERAL PROMUTAGENS & CARCINOGENS CONTAINING HALOALLYL OR HALOPROPYL SUBSTITUENTS EXCRETE SMALL AMT OF URINARY 2-HALOACRYLIC ACIDS SUCH AS 2-CHLOROACRYLIC ACID & 2,3-DICHLOROACRYLIC ACID FROM DIALLATE.

来源:Hazardous Substances Data Bank (HSDB)

代谢

二异丙酸酯异构体的代谢通过它们的亚砜形式，在小鼠肝微粒体氧化酶系统中形成2-氯丙烯醛，并在小鼠和大鼠体内及其肝脏氧化酶的制备中形成2,3-二氯-2-丙烯-1-磺酸。

METABOLISM OF DIALLATE ISOMERS PROCEEDS VIA THEIR SULFOXIDES TO FORM 2-CHLOROACROLEIN IN MOUSE HEPATIC MICROSOMAL OXIDASE SYSTEM & 2,3-DICHLORO-2-PROPENE-1-SULFONIC ACID IN MICE & RATS IN VIVO & THEIR LIVER OXIDASE PREPN.

来源:Hazardous Substances Data Bank (HSDB)

代谢

双丙胺、三丙胺和磺胺酯的提出的代谢物通过高效液相色谱（HPLC）和气相色谱（GLC）顶空分析被鉴定和定量为氯代丙烯醛和氯代烯丙基硫醇。定量关系表明，硫代氨基甲酸盐在混合功能氧化酶系统单独作用下代谢激活产生氯代丙烯醛，而当谷胱甘肽/谷胱甘肽-S-转移酶系统存在时，中间的S-氧化产物被转化为氯代烯丙基硫醇，从而解毒。三种化合物的主要小鼠微体混合功能氧化酶代谢物通过高效液相色谱共相色谱被鉴定为相应的亚磺酸酯。结论是，致突变氯代丙烯醛的形成主要涉及双丙胺的亚磺化，随后是sigma键迁移重排-1,2-消除反应，以及三丙胺和磺胺酯的S-亚甲基羟基化，然后是其α-羟基中间体的分解。谷胱甘肽-S-转移酶催化的与谷胱甘肽的竞争性共轭作用将亚磺化的中间体从涉及氯代丙烯醛形成的激活转向氯代烯丙基硫醇释放的解毒。

The proposed metabolites of diallate, triallate, and sulfallate were identified and quantitated by HPLC and GLC headspace analysis as chloroacroleins and chloroallylthiols. The quantitative relationships indicate that the thiocarbamates yield chloroacroleins on metabolic activation with the mixed function oxidase system alone, while the intermediate S-oxidation products were detoxified on diversion to chloroallylthiols when the glutathione/glutathione-S-transferase system was also present. The major mouse microsomal mixed function oxidase metabolites of three compounds were identified by HPLC cochromatography as the corresponding sulfoxides. It was concluded that the formation of mutagenic chloroacroleins involves primarily sulfoxidation of diallate followed by sigmatropic rearrangement-1,2-elimination reactions and S-methylene hydroxylation of triallate and sulfallate and then decomposition of their alpha-hydroxy intermediates. Competing glutathione-S-transferase catalyzed conjugations with glutathione divert the sulfoxidized intermediates from activation involving chloroacrolein formation to detoxification on chloroallylthiol liberation.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

美国环保局健康与环境评估办公室的人类健康评估小组对敌草快进行了致癌性评估。根据他们的分析，敌草快的证据权重为C组，这是基于动物中的有限证据。在人类中没有可用数据。作为C组化学物质，敌草快被认为是一种可能的 human致癌物。

The Human Health Assessment Group in EPA's Office of Health and Environmental Assessment has evaluated diallate for carcinogenicity. According to their analysis, the weight-of-evidence for diallate is group C, which is based on limited evidence in animals. No data is available in human. As a group C chemical, diallate is considered to be a possible human carcinogen.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

没有关于人类的数据。动物致癌性证据有限。总体评估：第3组：该物质对人类致癌性无法分类。

No data are available in humans. Limited evidence of carcinogenicity in animals. OVERALL EVALUATION: Group 3: The agent is not classifiable as to its carcinogenicity to humans.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌物分类

国际癌症研究机构致癌物：敌草快

IARC Carcinogenic Agent:Diallate

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

国际癌症研究机构（IARC）致癌物分类：第3组：对其对人类的致癌性无法分类

IARC Carcinogenic Classes:Group 3: Not classifiable as to its carcinogenicity to humans

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

国际癌症研究机构专著：第30卷：（1983年）杂项杀虫剂

IARC Monographs:Volume 30: (1983) Miscellaneous Pesticides

来源:International Agency for Research on Cancer (IARC)

吸收、分配和排泄

口服剂量大部分（88%）在48小时内消除。

ORAL DOSE LARGELY (88%) ELIMINATED IN 48 HR.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

在野燕麦中，主要的吸收是通过新生的鞘片。在幼苗发育的早期阶段，吸收量非常少。

IN WILD OAT, PRIMARY ABSORPTION IS THROUGH EMERGING COLEOPTILE. EXTREMELY MINOR UPTAKE AT EARLY STAGES OF SEEDLING DEVELOPMENT.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

... 野燕麦（Avena fatua L）、小麦（Triticum aestivum L Var Selkirk）、大麦（Hordeum vulgare L Vor Trail）、亚麻（Linum usitatissimum L Var Bolley）的根和鞘片对标记的二亚磷的碳吸收与转运进行了研究，并得出结论...吸收与移动的模式相似...

... UPTAKE & TRANSLOCATION OF (14)CARBON FROM LABELED DIALLATE BY ROOTS & COLEOPTILES OF WILD OAT (AVENA FATUA L), WHEAT (TRITICUM AESTIVUM L VAR SELKIRK), BARLEY (HORDEUM VULGARE L VOR TRAIL), FLAX (LINUM USITATISSIMUM L VAR BOLLEY), /WAS STUDIED/ & CONCLUDED ... PATTERN OF ... UPTAKE & MOVEMENT WAS SIMILAR ...

来源:Hazardous Substances Data Bank (HSDB)

反应信息

• 作为反应物：
  描述：

  二异丙基硫代氨基甲酸S-[(E)-2,3-二氯烯丙基]酯 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  [2,3] Sigmatropic rearrangement of -(3-chloroallyl) thiocarbamate sulfoxides followed by a 1,2-elimination reaction yielding unsaturated aldehydes and acid chlorides

  摘要：

  DOI：

  10.1016/s0040-4039(01)93566-x

文献信息

• Molecules having pesticidal utility, and intermediates, compositions, and processes, related thereto
  申请人：Dow AgroSciences LLC

  公开号：US20180279612A1

  公开（公告）日：2018-10-04

  This disclosure relates to the field of molecules having pesticidal utility against pests in Phyla Arthropoda, Mollusca, and Nematoda, processes to produce such molecules, intermediates used in such processes, pesticidal compositions containing such molecules, and processes of using such pesticidal compositions against such pests. These pesticidal compositions may be used, for example, as acaricides, insecticides, miticides, molluscicides, and nematicides. This document discloses molecules having the following formula (“Formula One”).

  这份披露涉及具有对节肢动物门、软体动物门和线虫门害虫具有杀虫效用的分子领域，用于生产此类分子的过程，用于此类过程的中间体，含有此类分子的杀虫组合物，以及使用此类杀虫组合物对抗此类害虫的过程。这些杀虫组合物可以用作螨虫剂、杀虫剂、螨虫剂、软体动物杀虫剂和线虫杀虫剂。本文件披露了具有以下式（“式一”）的分子。
• [EN] MOLECULES HAVING PESTICIDAL UTILITY, AND INTERMEDIATES, COMPOSITIONS, AND PROCESSES, RELATED THERETO<br/>[FR] MOLÉCULES PRÉSENTANT UNE UTILITÉ EN TANT QUE PESTICIDE, ET LEURS INTERMÉDIAIRES, COMPOSITIONS ET PROCÉDÉS
  申请人：DOW AGROSCIENCES LLC

  公开号：WO2017040194A1

  公开（公告）日：2017-03-09

  This disclosure relates to the field of molecules having pesticidal utility against pests in Phyla Arthropoda, Mollusca, and Nematoda, processes to produce such molecules, intermediates used in such processes, pesticidal compositions containing such molecules, and processes of using such pesticidal compositions aga inst such pests. These pesticidal compositions may be used, for example, as acaricides, insecticides, miticides, molluscicides, and nematicides. This document discloses molecules having the following formula ("Formula One").

  这份披露涉及具有对节肢动物门、软体动物门和线虫门害虫有用的分子领域，用于生产这种分子的过程，用于这种过程的中间体，含有这种分子的杀虫剂组合物，以及使用这种杀虫剂组合物对抗这些害虫的过程。这些杀虫剂组合物可以用作螨虫剂、杀虫剂、螨虫剂、软体动物杀虫剂和线虫杀虫剂。本文件披露了具有以下化学式（“化学式一”）的分子。
• MOLECULES HAVING PESTICIDAL UTILITY, AND INTERMEDIATES, COMPOSITIONS, AND PROCESSES, RELATED THERETO
  申请人：Dow AgroSciences LLC

  公开号：US20170210723A1

  公开（公告）日：2017-07-27

  This disclosure relates to the field of molecules having pesticidal utility against pests in Phyla Arthropoda, Mollusca, and Nematoda, processes to produce such molecules, intermediates used in such processes, compositions containing such molecules, and processes of using such molecules and compositions against such pests. These molecules and compositions may be used, for example, as acaricides, insecticides, miticides, molluscicides, and nematicides. This document discloses molecules having the following formula (“Formula One”).

  这份披露涉及具有对节肢动物门、软体动物门和线虫门害虫具有杀虫效用的分子领域，用于生产这种分子的过程，用于这种过程的中间体，含有这种分子的组合物，以及使用这种分子和组合物对抗这些害虫的过程。这些分子和组合物可以用作杀螨剂、杀虫剂、杀螨剂、杀软体动物剂和杀线虫剂。本文件披露了具有以下式（“式一”）的分子。
• Method for detecting uracil biosynthesis inhibitors and their use as herbicides
  申请人：——

  公开号：US20020058244A1

  公开（公告）日：2002-05-16

  This invention relates to a method for identifying compounds that specifically inhibit a metabolic target site or pathway in plants. Enzymes which are specifically affected by the method of the invention include plant pyrimidine biosynthetic pathway enzymes, and particularly the enzymes involved in the conversion of orotate to uridine-5′-monophosphate (UMP). Further, the invention relates to a method for control of undesirable monocotyledenous and dicotyledenous plant species.

  这项发明涉及一种识别特定抑制植物代谢靶点或途径的化合物的方法。受该发明方法特异影响的酶包括植物嘧啶生物合成途径酶，特别是参与将小嘌呤转化为尿苷-5'-磷酸（UMP）的酶。此外，该发明涉及一种控制不良单子叶和双子叶植物物种的方法。
• [DE] 2, 4, 6-PHENYLSUBSTITUIERTE CYCLISCHE KETOENOLE<br/>[EN] 2,4,6-PHENYL SUBSTITUTED CYCLIC KETOENOLS<br/>[FR] CETOENOLS CYCLIQUES SUBSTITUES PAR 2,4,6-PHENYLE
  申请人：BAYER CROPSCIENCE AG

  公开号：WO2004080962A1

  公开（公告）日：2004-09-23

  Die vorliegende Erfindung betrifft neue 2,4,6-phenylsubstituierte cyclische Ketoenole der Formel (I), in welcher W, X, Y und CKE die oben angegebene Bedeutung haben, mehrere Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel und/oder Herbizide. Ausserdem betrifft die Erfindung selektiv herbizide Mittel, die 2,4,6-phenylsubstituierte Ketoenole cyclische Ketoenole einerseits und eine die Kulturpflanzenverträglichkeit verbessernde Verbindung andererseits enthalten.

  本发明涉及新的2,4,6-苯基取代的环状酮烯醇化合物，其化学式为（I），其中，W、X、Y和CKE具有上述所述的含义，以及它们的制备方法和作为杀虫剂和/或除草剂的用途。此外，本发明涉及选择性除草剂，其包含一方面为2,4,6-苯基取代的酮烯醇环状酮烯醇，另一方面为改善作物耐受性的化合物。