4-甲氧甲苛苄基(R,S)顺、反-2,2-二甲基-3-异丁烯基环丙烷羧酸酯 | 34388-29-9

• 物质功能分类: 化学农药原药 - 杀虫剂 - 拟除虫菊脂杀虫剂
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 4-甲氧甲苛苄基(R,S)顺、反-2,2-二甲基-3-异丁烯基环丙烷羧酸酯
• 中文别名: 甲苄菊酯；甲醚菊酯；(1R,S)-顺、反式-2,2-二甲基-3-(2-甲基-1-丙烯基)环丙烷羧酸-4-(甲氧甲基)-苄基酯；2,2-二甲基-3-(2-甲基-1-丙烯基)-环丙烷羧酸4-(甲氧甲基)-苄基酯；对甲氧甲菊酯；4-甲氧甲基苄基菊酸酯
• 英文名称: Methothrin
• 英文别名: [4-(methoxymethyl)phenyl]methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate
• CAS: 34388-29-9
• 化学式: C₁₉H₂₆O₃
• mdl: MFCD01735827
• 分子量: 302.4
• InChiKey: GQNBIMLHUAWKHJ-UHFFFAOYSA-N

物化性质

• 沸点：
  403.44°C (rough estimate)
• 密度：
  1.1662 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.526
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  T
• 安全说明：
  S22,S36
• 危险类别码：
  R20/21/22,R36/37/38

制备方法与用途

毒性

大鼠急性经口LD₅₀ > 5000 mg/kg（4040 mg/kg），小鼠为2296 mg/kg（1747 mg/kg）。对豚鼠皮肤无刺激和致敏作用。大鼠经口最大无作用剂量为8.08 mg/kg（53.88 mg/kg），吸入安全浓度为9 mg/m³。动物体内无明显蓄积毒性，未见致突变作用。对鱼类高毒。

化学性质

工业品为(±)顺、反四种异构体的混合物，呈棕黄色油状液体。纯品为无色油状液体，沸点分别为142～144℃（2.666 Pa）、150～151℃（133.3 Pa）和350℃（1.01×10⁻⁵Pa），相对密度约为0.9，折射率n₂₀ᴰ为1.5132。能溶于乙醇、苯、甲苯等多种有机溶剂；难溶于水。常温下贮存稳定，对光不稳定，遇碱易分解。

用途

拟除虫菊酯类杀虫剂。具有沸点低、蒸气压高的特点，用于防治卫生害虫，可作为加工蚊香用，也是制造电热驱蚊片的主要原料。也可用1%甲醚菊酯煤油制剂，每立方米空间含药剂10 mL时，蚊子在8 min内全部击倒，24 h内死亡率达100%。

主要用于防治蚊蝇等害虫，常用来制作蚊香及电热驱蚊片，具有击倒速度快、驱避性能好、杀伤力强等特点。用于蚊香中一般含有效成分为0.35%，也可配制喷雾剂、气雾剂、熏蒸剂等。

属卫生杀虫剂，对蚊蝇等卫生害虫有良好的驱避性和较强的杀死能力。

生产方法

由菊酸钠与4-（甲氧甲基）苄氯在溶剂中成酯而得。中间体菊酸的制备：将甘氨酸加入氯化氢气体饱和无水乙醇中，加热回流至全溶，得甘氨酸乙酯盐酸盐。在亚硝酸钠水溶液中，加入2,5-二甲基-已-2,4-二烯（由丙酮与乙炔反应制得），滴加上述pH=1.0的甘氨酸乙酯盐酸盐的水溶液，反应温度为18-20℃，得重氮乙酸乙酯。加入沉淀铜催化剂和少量对甲苯酚，搅拌下回流至无氮气放出，收集114-121℃（3.33 kPa）馏分，制得菊酸乙酯。用氢氧化钠的乙醇溶液使之皂化，脱去乙醇，即为菊酸钠。

甲醚菊酯原油的有效成分含量≥85.0%，为棕红色透明液体。原料消耗定额：菊酸乙酯820 kg/t、4-（甲氧甲基）苄氯740 kg/t。

生产方法

1. 菊酸的制备 以丙酮和乙炔为基本原料，合成2,5-二甲基-2,4-己二烯，再在铜催化剂下与重氮乙酸酯成环，生成菊酸。

2. 4-（甲氧甲基）苄氯的制备 以对二甲苯为原料，经侧链氯化后制得对氯甲基苄氯，再进行醚化反应制得。

3. 甲醚菊酯的合成 由菊酸钠与4-（甲氧甲基）苄氯在溶剂中反应制得。操作过程是：将10 g菊酸乙酯，用氢氧化钠乙醇溶液皂化，脱去乙醇、水后，加极性非质子溶剂10 mL、4-（甲氧甲基）苄氯9 g、催化剂0.1 g，于85～90℃反应2 h。冷却，滤去氯化钠，减压蒸馏，得产品12.3 g (82%)，沸点为190℃/666.5 Pa，折射率n₂₀ᴰ为1.5150。

反应信息

• 作为产物：
  描述：

  菊甲酸 、 吡啶 、 (4-甲氧基甲基苯基)甲醇 、 氯化亚砜 以70%的产率得到
  参考文献：
  名称：

  GU, KEQUAN;ZOU, XINZHOU, INYUN XUASYUEH, 6,(1989) N, S. 22-25

  摘要：

  DOI：

文献信息

• Pesticidal composition and process for producing coated solid pesticides
  申请人：Syngenta Participations AG

  公开号：EP1454528A1

  公开（公告）日：2004-09-08

  The instant invention relates to a pesticidal composition and to a process for producing coated solid pesticides. Said pesticidal composition and process for the coating of a solid pesticide formulation with thermoplastic polymers comprise the steps of a) charging said solid pesticide formulation into the drum of a pan coater equipped with at least one spraying nozzle, with at least one gas inlet and with at least one gas outlet b) spraying a mixture of at least one solvent and at least one thermoplastic polymer emulsified therein through said spraying nozzle during the operation of the pan coater and simultaneously blowing a gas through said gas inlet into the drum. The process according to the instant invention enables the production of coated solid pesticides in a very simple process, without requiring any manual intervention during the operation, and yields coated solid pesticides with excellently uniform coating layers and having extraordinarily well controlled release property of active ingredients.

  该瞬时发明涉及一种杀虫剂组合物以及生产涂覆固体杀虫剂的方法。所述杀虫剂组合物和用热塑性聚合物对固体杀虫剂配方进行涂覆的方法包括以下步骤： a) 将固体杀虫剂配方装入配有至少一个喷雾喷嘴、至少一个气体进口和至少一个气体出口的盘式涂覆机的滚筒中 b) 在盘式涂覆机运行期间通过喷雾喷嘴喷洒至少一种溶剂和至少一种热塑性聚合物乳化的混合物，并同时通过气体进口向滚筒中吹气。 根据该瞬时发明的方法使得可以在非常简单的过程中生产涂覆的固体杀虫剂，无需在操作过程中进行任何手动干预，并且产生的涂覆固体杀虫剂具有优异的均匀涂层，并具有非常良好的活性成分释放性能。
• Electronic ID database and detection method for pesticide compounds in edible Agro-products based on GC-Q-Orbitrap
  申请人：CHINESE ACADEMY OF INSPECTION AND QUARANTINE

  公开号：US11181512B2

  公开（公告）日：2021-11-23

  Disclosed is an electronic ID database and detection method for pesticide compounds in edible agro-products based on GC-Q-Orbitrap. The electronic ID database includes a collection of various pesticide compounds electronic ID information and is sorted according to retention time in the electronic ID. The electronic ID contains pesticide compounds information, retention time, mass spectrum, fragment ions information and intelligent matching value. The detection method includes sample pretreatment procedures, setting GC-Q-Orbitrap operating conditions and screening procedures for pesticide residues in samples, wherein setting GC-Q-Orbitrap operating conditions includes setting suitable chromatography and mass spectrometry conditions. In pesticide residue screening procedures, firstly, the retention time is used to find out pesticide compounds in electronic ID database. If there is a match, the corresponding electronic ID information is extracted. Then the intelligent matching value is compared, if it is less than threshold value, the result is recorded and displayed, and the screening is completed.

  本发明公开了一种基于 GC-Q-Orbitrap 的食用农产品中农药化合物电子 ID 数据库和检测方法。电子标识数据库包括各种农药化合物电子标识信息的集合，并根据电子标识中的保留时间进行排序。电子 ID 包含农药化合物信息、保留时间、质谱、碎片离子信息和智能匹配值。检测方法包括样品前处理程序、GC-Q-Orbitrap 操作条件设置和样品中农药残留筛选程序，其中 GC-Q-Orbitrap 操作条件设置包括设置合适的色谱和质谱条件。在农药残留筛选程序中，首先利用保留时间在电子 ID 数据库中查找农药化合物。如果匹配，则提取相应的电子 ID 信息。然后比较智能匹配值，如果小于阈值，则记录并显示结果，完成筛选。
• GU, KEQUAN;ZOU, XINZHOU, INYUN XUASYUEH, 6,(1989) N, S. 22-25
  作者：GU, KEQUAN、ZOU, XINZHOU

  DOI：——

  日期：——
• ELECTRONIC ID DATABASE AND DETECTION METHOD FOR PESTICIDE COMPOUNDS IN EDIBLE AGRO-PRODUCTS BASED ON GC-Q-ORBITRAP
  申请人：CHINESE ACADEMY OF INSPECTION AND QUARANTINE

  公开号：US20210285921A1

  公开（公告）日：2021-09-16

  Disclosed is an electronic ID database and detection method for pesticide compounds in edible agro-products based on GC-Q-Orbitrap. The electronic ID database includes a collection of various pesticide compounds electronic ID information and is sorted according to retention time in the electronic ID. The electronic ID contains pesticide compounds information, retention time, mass spectrum, fragment ions information and intelligent matching value. The detection method includes sample pre-treatment procedures, setting GC-Q-Orbitrap operating conditions and screening procedures for pesticide residues in samples, wherein setting GC-Q-Orbitrap operating conditions includes setting suitable chromatography and mass spectrometry conditions. In pesticide residue screening procedures, firstly, the retention time is used to find out pesticide compounds in electronic ID database. If there is a match, the corresponding electronic ID information is extracted. Then the intelligent matching value is compared, if it is less than threshold value, the result is recorded and displayed, and the screening is completed.
• [EN] PESTICIDAL COMPOSITION AND PROCESS FOR PRODUCING COATED SOLID PESTICIDES<br/>[FR] COMPOSITION PESTICIDE ET PROCEDE DE PRODUCTION DE PESTICIDES SOLIDES ENROBES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2004077947A1

  公开（公告）日：2004-09-16

  The instant invention relates to a pesticidal composition and to a process for producing coated solid pesticides. Said pesticidal composition and process for the coating of a solid pesticide formulation with thermoplastic polymers comprise the steps of a) charging said solid pesticide formulation into the drum of a pan coater equipped with at least one spraying nozzle, with at least one gas inlet and with at least one gas outlet b) spraying a mixture of at least one solvent and at least one thermoplastic polymer emulsified therein through said spraying nozzle during the operation of the pan coater and simultaneously blowing a gas through said gas inlet into the drum. The process according to the instant invention enables the production of coated solid pesticides in a very simple process, without requiring any manual intervention during the operation, and yields coated solid pesticides with excellently uniform coating layers and having extraordinarily well controlled release property of active ingredients.