氨氟灵 | 29091-05-2

• 物质功能分类: 分析化学 - 标准品 - 农残、兽药及化肥类
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 氨氟灵
• 中文别名: 3-二乙基氨基-2,4-二硝基-6-三氟甲基苯胺；N3,N3-二乙基-2,4-二硝基-6-三氟甲基间苯二胺；敌乐胺；氨磺乐灵
• 英文名称: dinitramine
• 英文别名: N1,N1-diethyl-2,6-dinitro-4-trifluoromethyl-m-phenylenediamine；Caswell No. 335C；3-N,3-N-diethyl-2,4-dinitro-6-(trifluoromethyl)benzene-1,3-diamine
• CAS: 29091-05-2
• 化学式: C₁₁H₁₃F₃N₄O₄
• mdl: MFCD00144149
• 分子量: 322.244
• InChiKey: OFDYMSKSGFSLLM-UHFFFAOYSA-N

物化性质

• 熔点：
  98-99°C
• 沸点：
  409.1±45.0 °C(Predicted)
• 密度：
  1.4291 (estimate)
• 颜色/状态：
  Yellow crystals
• 溶解度：
  In acetone 1040, chloroform 670, benzene 473, xylene 227, ethanol 107, hexane 14 (all in g/L at 20 °C).
• 蒸汽压力：
  3.6X10-6 mm Hg at 25 °C
• 稳定性/保质期：
  常温常压下稳定
• 腐蚀性：
  Non-corrosive, except to polyvinyl plastic tubing.
• 解离常数：
  pKa = -7.18 (est)
• 保留指数：
  1817.8;1796.9

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  9

ADMET

代谢

N,N-二取代烷基氨基组（包括二硝胺）的脱烷基反应在鱼类中发生...

Dealkylation of the N,N-disubstituted alkylamino group /including dinitramine/ occurs in fish. ...

来源:Hazardous Substances Data Bank (HSDB)

代谢

/Dinitramine/在肝脏微粒体中通过侧链氧化和胺脱烷基化迅速代谢，产生多种极性和非极性代谢物，这些代谢物在粪便和尿液中等量排出。

... /Dinitramine is/ rapidly metabolized in liver microsomes by side-chain oxidation and amine-dealkylation to yield a variety of polar and non-polar metabolites which are excreted equally in feces and urine.

来源:Hazardous Substances Data Bank (HSDB)

代谢

使用的土壤真菌被鉴定为烟曲霉（Aspergillus fumigatus）、尖孢镰刀菌（Fusarium oxysporum）和拟青霉（Paecilomyces sp.）。当这些生物在培养中暴露于二硝基胺时，三种真菌都能降解除草剂。观察到定量差异。确定了四种代谢物，分别为单脱烷基和双脱烷基二硝基胺、乙基苯并咪唑和脱烷基苯并咪唑。烟曲霉的粗细胞提取物也能脱烷基化二硝基胺。放射性标记的二硝基胺（14C标记的氟、三氟甲基和环标记）被掺入阿纳海姆粉砂壤土中。八个月的分析期间发现存在三种化合物。可能还形成了多达十种其他未鉴定出的代谢物。二硝基胺在甲醇和水中迅速发生光解，半衰期为10分钟。使用质谱分析确定了四种化合物。

Soil fungi used were identified as Aspergillus fumigatus, Fusarium oxysporum and Paecilomyces sp. When these organisms were exposed in culture to dinitramine, all three degraded the herbicide. Quantitative differences were observed. Four metabolites were identified as the mono- and di-dealkylated dinitramine, the ethyl-benzimidazole, and the dealkylated benzimidazole. Crude cell extracts of aspergillus fumigatus also dealkylated dinitramine. Radioactive dinitramine (14)CF3 and (14)C-ring-labeled) was incorporated into Anaheim silty loam soil. Analyses over an eight month period revealed the presence of /three compounds/. Perhaps as many as ten other unidentified metabolites were also formed. Dinitramine underwent rapid photolytic decomposition in methanol and water with a 10 min half-life. Mass spectrum analyses were used to identify /four compounds/.

来源:Hazardous Substances Data Bank (HSDB)

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的程度。... 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，并给予静脉输注...生理盐水、林格溶液或林格乳酸盐，以恢复细胞外液体积和电解质。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 ... 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)

毒理性

• 解毒与急救

支持性措施通常足以成功管理对这些除草剂的过度暴露...。如果尽管有良好的支持性护理，患者的状况仍然恶化，应怀疑有其他替代或额外的有毒物质的作用。/其他除草剂/

Supportive measures are ordinarily sufficient for successful management of excessive exposures to these herbicides ... . If the patient's condition deteriorates in spite of good supportive care, the operation of an alternative or additional toxicant should be suspected. /Other herbicides/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

迹象和症状：可能会引起刺激。这些除草剂不会解开氧化磷酸化或生成变性血红蛋白。/氟硝基甲苯胺化合物/

/SIGNS AND SYMPTOMS/ May be irritating. These herbicides do not uncouple oxidative phosphorylation or generate methemoglobin. /Fluorodinitrotoluidine cmpd/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

选择性土壤除草剂，通过根系和茎叶吸收，很少转移到茎和叶，但稍微多转移到根部。

Selective soil-herbicide, absorbed by the roots and shoots, with very little translocation to the stems and leaves, and slightly more to the roots.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险品标志：
  Xn,N
• 安全说明：
  S36/37,S60,S61
• 危险类别码：
  R50/53,R21
• WGK Germany：
  3
• 海关编码：
  2921519011
• 危险品运输编号：
  UN 3077

制备方法与用途

化学性质
这是一种亮黄色固体，熔点为95-100℃。

用途
主要用于森林除草。

类别
属于农药类。

毒性分级
被归为中毒级别。

急性毒性
大鼠口服LD50值为3000毫克/公斤。

可燃性危险特性
燃烧时会生成有毒的氮氧化物和氟化物气体。

储运特性
应存放在通风、低温且干燥的库房内，并与食品原料分开储存和运输。

灭火剂
可用干粉、泡沫或砂土进行扑灭。

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  3-氯-N,N-二乙基-2,6-二硝基-4-(三氟甲基)苯胺	N,N-Diethyl-3-chloro-2,6-dinitro-4-trifluoromethylanilin	36438-51-4	C11H11ClF3N3O4	341.674

反应信息

• 作为反应物：
  描述：

  二硫化碳 、 氨氟灵 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以55%的产率得到7-diethylamino-6-nitro-4-trifluormethyl-2-benzothiazolinethione
  参考文献：
  名称：

  Rasheed, Khalid; Warkentin, James D., Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 1597 - 1600

  摘要：

  DOI：
• 作为产物：
  描述：

  3-氯-N,N-二乙基-2,6-二硝基-4-(三氟甲基)苯胺 在 氨 作用下， 以 1,4-二氧六环 为溶剂， 反应 40.0h， 生成 氨氟灵
  参考文献：
  名称：

  Synthesis and evaluation of oryzalin analogs against Toxoplasma gondii

  摘要：

  The synthesis and evaluation of 20 dinitroanilines and related compounds against the obligate intracellular parasite Toxoplasma gondii is reported. Using in vitro cultures of parasites in human fibroblasts, we determined that most of these compounds selectively disrupted Toxoplasma microtubules, and several displayed sub-micromolar potency against the parasite. The most potent compound was N(1),N(1)-dipropyl-2,6-dinitro-4-(trifluoromethyl)-1,3-benzenediamine (18b), which displayed an IC(50) value of 36 nM against intracellular T. gondii. Based on these data and another recent report [Ma, C.; Tran, J.; Gu, F.; Ochoa, R.; Li, C.; Sept, D.; Werbovetz, K.; Morrissette, N. Antimicrob. Agents Chemother. 2010, 54, 1453], an antimitotic structure-activity relationship for dinitroanilines versus Toxoplasma is presented. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.07.003

文献信息

• [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。
• 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] NOVEL HERBICIDES<br/>[FR] NOUVEAUX HERBICIDES
  申请人：SYNGENTA LTD

  公开号：WO2009015877A1

  公开（公告）日：2009-02-05

  Bicyclic dione compounds, and derivatives thereof, which are suitable for use as herbicides. formula (I)

  双环二酮化合物及其衍生物，适用于用作除草剂。公式（I）