特丁津 | 5915-41-3

• 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 - 有机杂环化合物 - 三嗪类
• 中文名称: 特丁津
• 中文别名: N2-特-丁基-6-氯-N4-乙某-1．3．5-三嗪-2,4-二胺；6-氯-N-(1,1-二甲乙基)-N’-乙基-1,3,5-三嗪-2,4-二胺；2-氯-4-特丁氨基-6-乙氨基-1,3,5-三嗪；草净津；N2-特-丁基-6-氯-N4-乙某-1,3,5-三嗪-2,4-二胺
• 英文名称: terbuthylazine
• 英文别名: 2-N-tert-butyl-6-chloro-4-N-ethyl-1,3,5-triazine-2,4-diamine
• CAS: 5915-41-3
• 化学式: C₉H₁₆ClN₅
• mdl: MFCD00055513
• 分子量: 229.713
• InChiKey: FZXISNSWEXTPMF-UHFFFAOYSA-N

物化性质

• 熔点：
  178°C
• 沸点：
  368.7°C (rough estimate)
• 密度：
  1.1880
• 闪点：
  11 °C
• 溶解度：
  DMF：30mg/mL； DMSO：30mg/mL；乙醇：1mg/mL
• LogP：
  3.210
• 颜色/状态：
  Colorless powder
• 气味：
  Rancid, putrid
• 蒸汽压力：
  0.09 mPa (6.75X10-7 mm Hg) at 25 °C
• 大气OH速率常数：
  1.10e-11 cm3/molecule*sec
• 稳定性/保质期：

  在常温常压下保持稳定

• 分解：
  When heated to decomposition it emits very toxic fumes of /hydrogen chloride and nitrogen oxides/.
• 腐蚀性：
  Non-corrosive
• 解离常数：
  pKa = 2.0; very weak base
• 碰撞截面：
  153.48 Ų [M+H]+ [CCS Type: TW]
• 保留指数：
  1728;1755;1754;1761.6;1747.6;1755.8

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  62.7
• 氢给体数：
  2
• 氢受体数：
  5

ADMET

代谢

大鼠对特丁津的代谢与其他氯代-s-三嗪类除草剂相似。主要的代谢途径是氯基的水解以及一元或二元脱烷基化。一个或两个脱烷基化胺基的羟基化也可能发生。

Metabolism of terbuthylazine in rats is similar to other chloro-s-triazine herbicides. The major routes of metabolism are hydrolysis of the chlorine moiety and mono- or didealkylation. Hydroxylation of one or both of the dealkylated amine groups may also occur.

来源:Hazardous Substances Data Bank (HSDB)

代谢

尿液和粪便中分别含有高达25种和15种已识别的代谢物，其中大多数是极性的。三嗪环的降解没有发生。在所有三嗪中都常见的两种脱氯和脱烷基化/羟基化代谢物，即氨基三唑和氨基三唑，在粪便中含量较低。

Urine and feces contained up to 25 and 15 identified metabolites, respectively, most of which were polar. Degradation of the triazine ring did not occur. Ammeline and ammelide, 2 dechlorinated and dealkylated/hydroxylated metabolites common to all triazines, were identified in low amounts in the feces.

来源:Hazardous Substances Data Bank (HSDB)

代谢

在哺乳动物中，口服给药后，会迅速形成一个去乙基代谢物，随后是由 tert-丁基部分的一个甲基氧化产生的产物的结合物。所有这些物质都会被迅速排出体外。

In mammals, following oral administration, ...a de-ethyl metabolite forms rapidly, followed by conjugates of products formed by oxidation of one methyl group of the tert-butyl moiety. All are rapidly excreted.

来源:Hazardous Substances Data Bank (HSDB)

代谢

/Terbutylethylazine/ 在玉米、高粱和甘蔗的叶片中迅速代谢成水溶性化合物，而在易感的大麦中代谢较慢，通过谷胱甘肽或γ-谷氨酰半胱氨酸取代2-氯基团。

/Terbutylethylazine/ was rapidly metabolized to water soluble compounds in the leaves of corn, sorghum, and sugar cane and more slowly in susceptible barley, by displacement of the 2-chloro group with glutathione or gamma-glutamylcysteine.

来源:Hazardous Substances Data Bank (HSDB)

代谢

除草剂（包括莠去津以及另外三种三嗪类除草剂，特丁津、氨甲基三嗪和特丁腈）的代谢已经在体外在大鼠、猪和人的肝脏微粒体中进行了研究。所有三种物种的主要一相反应是N-单脱烷基化、对异丙基或叔丁基基团的羟基化以及底物的亚磺酰化。尽管所有物种都产生了相同类型的代谢物，但在代谢物比例上存在物种特异性的差异。随后的研究表明，细胞色素P450 1A2是人类肝脏微粒体中参与S-三嗪代谢的主要一相酶。/三嗪类除草剂/

The metabolism of atrazine (and three other triazine herbicides, terbuthylazine, ametryne, and tebutryne) has been investigated in vitro in liver microsomes from rats, pigs, and humans. The principal phase-1 reactions in all three species were N-monodealkylation, hydroxylation of the isopropyl or tert-butyl moiety and sulfoxidation of the substrate. Although all species produced the same type of metabolites, there were spiecies specific differences in the metabolite ratios. Subsequent studies have shown that cytochrome P450 1A2 is the major phase-1 enzyme involved in the metabolism of s-triazine in human liver micrsomes. /Triazine herbicides/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

癌症分类：D组 不可归入人类致癌性类别

Cancer Classification: Group D Not Classifiable as to Human Carcinogenicity

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 毒性数据

LC50 (大鼠) > 3,510 毫克/立方米/4小时

LC50 (rat) > 3,510 mg/m3/4h

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

毒理性

• 解毒与急救

皮肤去污。皮肤污染应立即用肥皂和水清洗处理。眼睛污染应立即用大量清水长时间冲洗。如果皮肤或眼睛刺激持续存在，应立即获得医疗注意。/其他除草剂/

Skin decontamination. Skin contamination should be treated promptly by washing with soap and water. Contamination of the eyes should be treated immediately by prolonged flushing of the eyes with large amounts of clean water. If dermal or ocular irritation persists, medical attention should be obtained without delay. /Other herbicides/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

胃肠道去污染。摄入这些除草剂后可能会出现呕吐和腹泻，这是由于它们的刺激性特性。管理取决于：（1）摄入量的最佳估计，（2）摄入后经过的时间，（3）受试者的临床状况。活性炭可能有效于限制刺激性效果并减少大部分或所有这些除草剂的吸收。氢氧化铝抗酸剂可能有助于中和更酸性物质的刺激性作用。如果肠道有声音且自发腹泻尚未开始，应给予山梨醇以诱导泻药。脱水和电解质紊乱可能严重到需要口服或静脉输液。 ... 如果摄入了大量除草剂，并且患者在摄入后一小时内就诊，应考虑胃肠道去污染。如果摄入的除草剂量较小，如果已经发生了有效的呕吐，或者如果治疗延迟，通过口腔给予活性炭和山梨醇。 /其他除草剂/

Gastrointestinal decontamination. Ingestions of these herbicides are likely to be followed by vomiting and diarrhea due to their irritant properties. Management depends on: (1) the best estimate of the quantity ingested, (2) time elapsed since ingestion, and (3) the clinical status of the subject. Activated charcoal is probably effective in limiting irritant effects and reducing absorption of most or all of these herbicides. Aluminum hydroxide antacids may be useful in neutralizing the irritant actions of more acidic agents. Sorbitol should be given to induce catharsis if bowel sounds are present and if spontaneous diarrhea has not already commenced. Dehydration and electrolyte disturbances may be severe enough to require oral or intravenous fluids. ... If large amounts of herbicide have been ingested and the patient is seen within an hour of the ingestion, gastrointestinal decontamination should be considered ... . If the amount of ingested herbicides was small, if effective emesis has already occurred, or if treatment is delayed, administer activated charcoal and sorbitol by mouth. /Other herbicides/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

静脉输液。如果由于呕吐和腹泻已经出现了严重的脱水和电解质流失，监测血液电解质和液体平衡，并给予葡萄糖、生理盐水、林格溶液或林格乳酸盐的静脉输注，以恢复细胞外液容量和电解质。一旦能够保留液体，随即给予口服营养。/其他除草剂/

Intravenous fluids. If serious dehydration and electrolyte depletion have occurred as a result of vomiting and diarrhea, monitor blood electrolytes and fluid balance and administer intravenous infusions of glucose, normal saline, Ringer's solution, or Ringer's lactate to restore extracellular fluid volume and electrolytes. Follow this with oral nutrients as soon as fluids can be retained. /Other herbicides/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

在大鼠代谢研究中，给Wistar大鼠口服了（14）C-特丁津（3.6毫克）。特丁津迅速（50%在16-17小时内排出）且完全代谢，并未在组织中积累。在雄性大鼠中，放射性物质在尿液和粪便中均匀排泄，但在雌性大鼠中，约66%的放射性标记物通过尿液排出。

In a rat metabolism study, (14)C-terbuthylazine (3.6 mg) was administered orally to Wistar rats. Terbuthylazine was rapidly (50% excreted by 16-17 hrs) and completely metabolized and did not accumulate in tissues. Radioactivity was excreted equally in urine and feces in males, but in females about 66% of the radiolabel was excreted in the urine.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

在哺乳动物中，口服给药后，72-84%在24小时内通过尿液和粪便排出，几乎所有的在48小时内排出。

In mammals, following oral administration, 72-84% is eliminated in the urine and feces within 24 hr, and almost all within 48 hr.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

特丁津（TBA）是一种在玉米种植中广泛使用的除草剂。本文评估了将头发中的TBA作为暴露生物标志物的测量方法。五只Sprague Dawley大鼠连续三天通过胃管给药TBA，然后剃掉背部毛发并分析TBA。此外，在应用季结束时，收集了10名玉米农民、9名农村居民和6名城市居民的头发样本。通过溶剂提取后的液相色谱-三重四极杆质谱法检测头发中的TBA。所有大鼠样本中的TBA均可量化，平均浓度为0.92（±0.26）ng/mg，对应的掺入率为0.12%。所有农民样本中的TBA均可量化（中位数：0.67 ng/mg），75%的农村居民样本中可量化（0.01 ng/mg），而城市居民样本中均未检测到（<0.01 ng/mg），各组之间存在统计学差异（P<0.01）。我们的结果表明TBA会掺入头发中，并促使进一步研究头发TBA作为累积暴露潜在生物标志物的使用。

Terbuthylazine (TBA) is an herbicide widely used in corn cultivation. Herein we evaluate the measurement of hair TBA as biomarkers of exposure. Five Sprague Dawley rats were gavaged with TBA for 3 days, and then the back hair was shaved and analyzed for TBA. In addition, head hair samples from 10 corn farmers, 9 rural residents, and 6 urban residents were collected at the end of the application season. Hair TBA was detected by liquid chromatography triple quadrupole mass spectrometry after solvent extraction. TBA was quantifiable in all rat samples with a mean concentration of 0.92 (+ or - 0.26)ng/mg, which corresponds to a 0.12% incorporation rate. TBA was quantifiable in all farmer samples (median: 0.67 ng/mg), in 75% of rural resident samples (0.01ng/mg) and in none of the urban resident samples (<0.01 ng/mg), with a statistical difference among groups (P<0.01). Our results suggest that TBA is incorporated in hair and prompt further investigation on the use of hair TBA as a potential biomarker of cumulative exposure.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险品标志：
  Xn,F,T
• 安全说明：
  S16,S24,S36,S45,S7
• 危险类别码：
  R11
• WGK Germany：
  2
• 危险品运输编号：
  UN1230 3/PG 2
• 包装等级：
  I; II; III
• 危险类别：
  6.1
• 储存条件：
  常温下，应避光存放于阴凉干燥处，并密封保存。

制备方法与用途

生物活性

Terbuthylazine 是一种乙酰乳酸合酶 (ALS) 抑制剂，属于选择性除草剂。

用途

• 用于防除大多数杂草
• 芽前施用适用于多种作物，也可选择性地防除柑橘、玉米和葡萄园中的杂草。
• 在高粱田中推荐使用剂量为 1.2～1.8 kg AI/ha。

类别

农药

毒性分级

中毒

急性毒性

• 口服 - 大鼠 LD50: 1845 毫克/公斤
• 吸入 - 大鼠 LC50: >3510 毫克/立方米（4小时）

可燃性危险特性

燃烧会产生有毒氯化物和氮氧化物气体。

储运特性

库房应保持通风、低温和干燥；与食品原料分开储存和运输。

灭火剂

干粉、泡沫或砂土。

反应信息

• 作为反应物：
  描述：

  特丁津 在 immobilized layer of TiO₂/chitosan 作用下， 反应 1.33h， 生成 氰尿酸
  参考文献：
  名称：

  Photocatalytic degradation of the herbicide terbuthylazine: Preparation, characterization and photoactivity of the immobilized thin layer of TiO2/chitosan

  摘要：

  The aim of this study was to immobilize a photocatalytic TiO2 layer on a suitable support material for potential use in a variety of photoreactor designs. The immobilized TiO2/chitosan thin film was used for the photocatalytic treatment of a triazine herbicide, terbuthylazine as representative agrochemical pollutant in the wastewater. The method of preparation was based on the use of a chitosan as binder and glass fiber woven roving material as a support. The employed method was found to be very simple, low cost and quite effective. Several methods of the photocatalyst characterization, such as FE-SEM/EDX, AAS, ICP-MS, TOC and nitrogen adsorption/desorption at 77K were employed to correlate structural and morphological properties of immobilized TiO2-chitosan/glass fiber woven roving and its photocatalytic properties under UV irradiation. Reaction was performed in a self-constructed batch mode and annular type of the photoreactor. Comparison of thermal, photolytic and photocatalytical degradation of treated terbuthylazine at different reaction conditions was performed in order to get more insight into the photocatalytic performance and reaction mechanism. It was observed that there is no decay in photocatalytic efficiency over a long period of reaction time using for the photocatalytic degradation of terbuthylazine. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2015.04.021
• 作为产物：
  描述：

  2-(叔丁基氨基)-4,6-二氯-1,3,5-三嗪 、 乙胺 在 sodium hydroxide 作用下， 以 水 为溶剂， 生成 特丁津
  参考文献：
  名称：

  一种多釜串联三嗪类除草剂连续生产方法

  摘要：

  本发明涉及一种多釜串联三嗪类除草剂连续生产方法，计量好的三聚氯氰溶液经过预冷后与烷胺基R1在混合器混合后进入一段反应釜，并连续出料经过换热器后与碱在混合器中中和进入一段中和釜，完成一段反应后经过连续分水器、换热器后与烷胺基R2在混合器混合后进入二段反应釜，连续出料经过换热器后与碱在混合器中混合进入二段中和釜，中和后经连续分层器分出水相后脱除溶剂干燥得到三嗪类产品。该生产方法具有产能高，生产稳定性好，效率高，产品质量高等特点，特别适合于现有生产企业进行技术改造，且改造费用较低、基本不添加新的反应设备，技术易于为现有企业掌握。

  公开号：

  CN109627225B

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。

表征谱图