磺乐灵 | 4726-14-1

• 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 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 磺乐灵
• 中文别名: 甲磺乐灵
• 英文名称: nitralin
• 英文别名: N-bis-(n-propyl)-2,6-dinitro-4-methylsulfonylaniline；Caswell No. 578；4-methylsulfonyl-2,6-dinitro-N,N-dipropylaniline
• CAS: 4726-14-1
• 化学式: C₁₃H₁₉N₃O₆S
• 分子量: 345.376
• InChiKey: UMKANAFDOQQUKE-UHFFFAOYSA-N

物化性质

• 熔点：
  151-152℃
• 沸点：
  507.2±50.0 °C(Predicted)
• 密度：
  1.3809 (rough estimate)
• 物理描述：
  Nitralin is a light yellow to orange solid with a mild odor. Sinks in water. (USCG, 1999)
• 颜色/状态：
  GOLDEN-ORANGE CRYSTALLINE SOLID
• 气味：
  MILD CHEMICAL ODOR
• 溶解度：
  SOLUBILITY @ 22 °C: 0.6 MG/L IN WATER; 360 G/L IN ACETONE; 330 G/L IN DIMETHYLSULFOXIDE; POORLY SOL IN COMMON HYDROCARBON AND AROMATIC SOLVENTS AND IN COMMON ALCOHOLS
• 蒸汽压力：
  9.3X10-9 mm Hg at 20 °C; 3.3X10-8 mm Hg at 30 °C
• 稳定性/保质期：

  燃烧会产生有毒的氮氧化物和氮氧化合气体。

• 自燃温度：
  435 °F (USCG, 1999)
• 腐蚀性：
  Noncorrosive
• 保留指数：
  2447;2411.8;2423.2;2407.4

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  137
• 氢给体数：
  0
• 氢受体数：
  7

ADMET

代谢

PLANAVIN 以 5 PPM 的浓度通过饲料给了一头插有导管的泌乳期奶牛喂食了 4 天。通过电子亲和力 & 硫火焰光度气相色谱分析，在牛奶、尿液或粪便中没有检测到 PLANAVIN 或可能的含硫代谢物。硫检测器显示，这种除草剂在新鲜瘤胃液中迅速（15分钟）分解，产生了三种含硫的代谢物，但代谢物尚未明确鉴定。

PLANAVIN WAS FED TO A CATHETERIZED LACTATING COW AT 5 PPM IN THE FEED RATION FOR 4 DAYS. PLANAVIN OR POSSIBLE SULFUR-CONTAINING METABOLITES WERE NOT DETECTED IN MILK, URINE OR FECES BY ELECTRON AFFINITY & SULFUR-FLAME PHOTOMETRIC GAS CHROMATOGRAPHIC ANALYSIS. THE SULFUR DETECTOR SHOWED THAT THE HERBICIDE RAPIDLY (15 MIN) DECOMPOSED IN FRESH RUMEN FLUID WITH PRODUCTION OF THREE SULFUR-CONTAINING /SRP: METABOLITES NOT DEFINATELY IDENTIFIED/.

来源:Hazardous Substances Data Bank (HSDB)

代谢

植物代谢物是2,6-二硝基-4-甲磺酰基-N-丙基苯胺，2,6-二硝基-4-甲基磺酰苯胺和2,6-二硝基-4-甲磺酰基苯酚。

Plant metabolites are 2,6-dinitro-4-methylsulfonyl-N-propylaniline, 2,6-dinitro-4-methyl-sulphonylaniline /and/ 2,6-dinitro-4-methylsulfonylphenol.

来源:Hazardous Substances Data Bank (HSDB)

代谢

(14)C-Nitralin 以 150 mg/kg 的剂量口服给予大鼠。给药后 0-72 小时内，放射性物质定量地（199.8%）分布。其中大部分在尿液和粪便中均匀分布；1.5% 在尸体皮肤和肠道中找到。尿液代谢物的结构分析表明，代谢过程通过一系列复杂的多步骤生物转化进行，涉及硝基团还原、侧链氧化和去除，随后形成多种杂环结构。一个主要的代谢物是 7-氨基-2-乙基-5-甲基磺酰基-1-丙基苯并咪唑；这仅占摄入放射性的 3-4%，是产量为 5 种代谢物中的一种。还鉴定出了另外七种代谢物，其中没有一种来自 Nitralin 的单步生物转化。后者的简单代谢物在将 Nitralin 与用于微生物诱变活性测试的大鼠肝脏酶一起培养时被检测到。在好氧条件下观察到两条途径（硝基还原和 N-脱烷基化），但在厌氧条件下，前者大大占优势。

(14)C-Nitralin was dosed orally to rats 150 mg/kg). The radioactivity was quantitatively (199.8%) between 0-72 hr after dosing. Most of this was distributed equally between the urine and feces; 1.5% was found in the carcass skin and intestines. Structural analysis of the urinary metabolites showed that the metabolism proceeded via a complex multistep series of biotransformations involving nitro-group reduction side-chain oxidation and removal and the subsequent formation of a variety of heterocyclic ring structures. A major metabolite was 7-amino-2-ethyl-5-methylsulfonyl-1-propylbenzimidazole; this accounted for only 3-4% of the ingested radioactivity and was 1 of 5 metabolites produced in this yield. Seven other metabolites were identified none of which was derived from single-step biotransformation of nitralin. The latter simpler metabolites were detected on the incubation of nitralin with rat liver enzymes of the type used in microbial mutagenicity testing. Two pathways nitro-reduction and N-dealkylation) were observed under aerobic conditions but the former greatly predominated under anaerobic conditions.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 副作用

皮肤致敏剂 - 一种可以诱导皮肤产生过敏反应的制剂。

Skin Sensitizer - An agent that can induce an allergic reaction in the skin.

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

毒理性

• 人类毒性摘录

一位50岁的工厂工人出现了瘙痒性鳞状红斑，被发现对4-甲磺酰-2,6-二硝基-N,N-二丙基苯胺（DNA-硝基萘）敏感；还检测到了对二硝基氯苯的交叉敏感性。...

A pruritic scaly erythema developed in a 50-yr-old factory worker who was found to be sensitive to 4-methylsulfonyl-2,6-dinitro-N,N-dipropyianiline (DNA-nitralin); cross-sensitivity to dinitrochlorobenzene was also detected. ...

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

在大鼠和狗的两年喂养试验中，“无影响”水平为每千克饮食2000毫克。

IN 2-YEAR FEEDING TRIALS 'NO EFFECT' LEVELS FOR RATS AND DOGS WAS 2000 MG/KG DIET.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

AT.../10-4摩尔硝雷灵/净磷吸收/在分离的线粒体中/高粱和玉米中减少了超过50%。在大豆中，硝雷灵@ 10-6摩尔浓度下的磷吸收减少了同样的程度。

AT.../10-4 MOLAR NITRALIN/ NET PHOSPHORUS UPTAKE /IN ISOLATED MITOCHONDRIA/ WAS REDUCED BY MORE THAN 50% IN SORGHUM & CORN. PHOSPHORUS UPTAKE IN SOYBEAN WAS REDUCED BY SAME MAGNITUDE WITH.../NITRALIN/ CONCN @ 10-6 MOLAR.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

一些轻微的症状，如轻度流涎和腹泻，是在给实验室动物喂食过量时引起的。

A FEW SIGNS SUCH AS MILD SALIVATION & DIARRHEA HAVE BEEN ELICITED BY FEEDING LABORATORY ANIMALS EXCESSIVE AMOUNTS.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

NITRALIN不通过植物叶片吸收，因此不是一种苗后除草剂。植物种子或根部的吸收是通过水的吸胀作用介导的。

NITRALIN IS NOT ABSORBED BY PLANT FOLIAGE & THEREFORE IS NOT A POSTEMERGENCE HERBICIDE. ABSORPTION BY SEED OR ROOTS OF PLANTS IS MEDIATED BY IMBIBITION OF WATER.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

Nitralin作为(14)C-环标记的化合物，已经在修改田间条件下种植的大豆、花生、豌豆和胡萝卜中进行了研究，其中除草剂以0.6、0.75和1.0磅/英亩的量分别掺入土壤。在大豆中，整株植物含有相当于0.02 ppm的Nitralin。种子中的Nitralin含量小于0.01 ppm。同样，花生和豌豆的整株植物部分含有相当于0.03 ppm的Nitralin，其中种子的含量范围与大豆相似。胡萝卜在大豆初始掺入研究后的11周，在温室条件下种植...。种植后6周，收获胡萝卜，并将根部分为皮和核心进行分析。根部含有0.006 ppm的Nitralin，其中78%和22%的放射性分别存在于皮和核心中。

Nitralin, as the (14)C-ring-labeled cmpd, has been studied in soybeans, peanuts, peas, and carrots grown under modified field conditions in which the herbicide was soil incorporated at 0.6, 0.75, and 1.0 lb/acre, respectively. In soybeans, the whole plant contained 0.02 ppm equivalents of nitralin. The seeds contained less than 0.01 ppm equivalents of nitralin. Similarly, whole plant parts from peanuts and peas contained an equivalent of 0.03 ppm equivalents of nitralin, with the seeds in a range similar to that of soybeans. Carrots were grown...under greenhouse conditions 11 wk after the initial incorporation study with soybeans. Six wk after planting, carrots were harvested and the roots were divided into peel and cores for analysis. The roots contained 0.006 ppm equivalents of nitralin with 78 and 22% of the radioactivity residing in the peel and cores, respectively.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

(14)C-环标记的硝哒嗪被喂给大鼠后，迅速被排出，其中52%的放射性物质出现在尿液中，47%出现在粪便中。在代谢笼中进行的实验中没有观察到(14)CO2。观察到了多种代谢产物。根西奶牛在其饲料中添加了50 ppm的硝哒嗪。检查牛奶未发现硝哒嗪或其降解产物4-甲磺酰-2,6-二硝基-N-丙基苯胺、4-甲磺酰-2,6-二硝基酚和4-甲磺酰-2,6-二硝基苯胺的残留。各种组织、粪便和尿液的检测也未发现硝哒嗪或4-甲磺酰-2,6-二硝基酚的残留。

(14)C-ring-labeled nitralin fed to rats was rapidly excreted, with 52% of the radioactivity being in the urine and 47% in the feces. No (14)CO2 was observed in an expt run in a metabolism cage. Multiple metabolic products were observed. Guernsey cows were fed nitralin at 50 ppm in their ration. Exam of milk revealed no detectable residues of nitralin or its degradation products 4-methylsulfonyl-2,6-dinitro-N-propylaniline, 4-methylsulfonyl-2,6-dinitrophenol and 4-methylsulfonyl-2,6-dinitroaniline. Analyses of various tissues, feces, and urine showed no detectable residues of nitralin or 4-methylsulfonyl-2,-6-dinitrophenol.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险品标志：
  N
• 安全说明：
  S60,S61
• 危险类别码：
  R50
• WGK Germany：
  2
• 危险品运输编号：
  UN 3077 9/PG 3

制备方法与用途

类别：农药
毒性分级：中毒
急性毒性：口服-大鼠 LD50: 2000 毫克/公斤；口服-小鼠 LD50: 2000 毫克/公斤
可燃性危险特性：燃烧时产生有毒氮氧化物和氮氧化合气体
储运特性：应存放在通风、低温、干燥的库房中，并与食品原料分开存储和运输
灭火剂：干粉、泡沫、砂土

反应信息

• 作为反应物：
  描述：

  戊炔草胺 、 maleic acid monohydrazide 、 3-氨基-1,2,4-三氮唑 、 monosodium methanearsonate 、 Disodium methylarsonate 、 双苯酰草胺 、 、 地乐灵 、 磺乐灵 、 、 4-氨基-3,5,6-三氯吡啶羧酸 、 2,3-二氯-1,4-萘醌 、 敌灭生 、 、 、 百草枯 、 、 、 异恶草酮 、 N-(1-ethylpropyl)-3,4-dimethyl-2,6-dinitrobenzamide 、 氟草敏 、 生成 2-氯-N,N-二烯丙基乙酰胺
  参考文献：
  名称：

  6-arylpyrimidines and herbicidal use

  摘要：

  一类6-芳基嘧啶类化合物可用于除草，其一般式为：##STR1##其中R.sup.2选自氢、卤素、取代或未取代的烷基、卤代烷基、多卤代烷基、卤代烯基、多卤代烯基、卤代炔基、多卤代炔基、烯基、炔基、烷氧基、烷硫基、烷氧羰基烷基、氰基、烷氧基烷基、烷氧羰基、环烷基、芳基烷基、烷基氨基、二烷基氨基或二烷基氨基羰基；R.sup.3为烷基、烯基、炔基或卤代烷基；R.sup.5为烷基、烯基、炔基、烯炔基或烷氧基烷基；R.sup.6为芳基（例如芳香环）；X为氧或硫。R.sup.2和R.sup.3可以形成融合环。

  公开号：

  US05397767A1
• 作为产物：
  描述：

  4-氯-3,5-二硝基苯基甲基砜 、 二正丙胺 以87%的产率得到
  参考文献：
  名称：

  ECKSTEIN Z.; EJMOCKI Z.; KAMINSKI J., PRZ. CHEM., 1979, 58, NO 7, 359-362

  摘要：

  DOI：

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。
• HYDRAZONYL GROUP-CONTAINING CONDENSED HETEROCYCLIC COMPOUND OR SALT THEREOF, AGRICULTURAL AND HORTICULTURAL INSECTICIDE COMPRISING THE COMPOUND, AND METHOD FOR USING THE INSECTICIDE
  申请人：Nihon Nohyaku Co., Ltd.

  公开号：US20190177319A1

  公开（公告）日：2019-06-13

  An object of the present invention is to develop and provide a novel agricultural and horticultural insecticide in view of the still immense damage caused by insect pests etc. and the emergence of insect pests resistant to existing insecticides in crop production in the fields of agriculture, horticulture and the like. Provided is a hydrazonyl group-containing condensed heterocyclic compound or a salt thereof, preferably a condensed heterocyclic compound represented by the general formula (1): wherein R 1 represents, for example, an alkyl group, R 2 represents, for example, a hydrogen atom, R 3 and R 4 each represent, for example, an alkyl group, a haloalkyl group or an acyl group, A 1 represents, for example, a nitrogen atom, A 2 represents, for example, N-Me or an oxygen atom, A 3 represents, for example, a carbon atom or a nitrogen atom, A 4 represents, for example, C—H, m represents, for example, 2, and n represents, for example, 1}, or a salt thereof; an agricultural and horticultural insecticide comprising the compound or a salt thereof as an active ingredient; and a method for using the insecticide.

  本发明的一个目的是开发并提供一种新型农艺和园艺杀虫剂，鉴于昆虫害虫等造成的损害仍然巨大，以及在农业、园艺等领域作物生产中出现的对现有杀虫剂具有抗性的昆虫害虫。 提供了一种含有肼酰基的稠合杂环化合物或其盐，优选为通式(1)表示的稠合杂环化合物： 其中R1代表例如烷基，R2代表例如氢原子，R3和R4各自代表例如烷基、卤代烷基或酰基，A1代表例如氮原子，A2代表例如N-Me或氧原子，A3代表例如碳原子或氮原子，A4代表例如C—H，m代表例如2，n代表例如1}，或其盐；一种包含该化合物或其盐作为活性成分的农艺和园艺杀虫剂；以及使用该杀虫剂的方法。
• [EN] MACROCYCLIC PICOLINAMIDES AS FUNGICIDES<br/>[FR] PICOLINAMIDES MACROCYCLIQUES À UTILISER EN TANT QUE FONGICIDES
  申请人：DOW AGROSCIENCES LLC

  公开号：WO2017116954A1

  公开（公告）日：2017-07-06

  The invention relates to macrocyclic picolinamides of Formula (I) and their use as fungicides.

  本发明涉及式(I)所示的大环吡啶酰胺及其作为杀菌剂的应用。

表征谱图