环丙津 | 22936-86-3

• 物质功能分类: 化学农药原药 - 除草剂 - 三氮苯类除草剂
• 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: 环丙津
• 中文别名: 环草津
• 英文名称: cyprazine
• 英文别名: 2-chloro-4-isopropylamino-6-cyclopropylamino-1,3,5-triazine；6-chloro-4-N-cyclopropyl-2-N-propan-2-yl-1,3,5-triazine-2,4-diamine
• CAS: 22936-86-3
• 化学式: C₉H₁₄ClN₅
• 分子量: 227.697
• InChiKey: OOHIAOSLOGDBCE-UHFFFAOYSA-N

物化性质

• 熔点：
  167°C
• 沸点：
  366°C (rough estimate)
• 密度：
  1.2385 (rough estimate)
• 颜色/状态：
  WHITE CRYSTALS
• 气味：
  ODORLESS
• 闪点：
  325 °F (OPEN CUP)
• 溶解度：
  31570.0 ppm in acetonitrile at 25 °C; 15470.0 ppm in toluene at 25 °C; 7280.0 ppm in benzene at 25 °C; 2230.0 ppm in carbon tetrachloride at 25 °C; 10.0 ppm in n-hexane at 25 °C; 233429.0 ppm in dimethylformamide at 25 °C; 190710.0 ppm in acetic acid @ 25 °C; 142430.0 ppm in acetone @ 25 °C; 94290.0 ppm in ethyl acetate @ 25 °C; 73820.0 ppm in chloroform @ 25 °C; 52860.0 ppm in ethanol @ 25 °C
• 蒸汽压力：
  3X10-7 mm Hg @ 20 °C
• 稳定性/保质期：
  燃烧会产生有毒的氮氧化物和氯化物气体。
• 分解：
  When heated to decomposition it emits /hydrogen chloride and nitrogen oxides/.
• 腐蚀性：
  NONCORROSIVE UNDER NORMAL USE CONDITIONS
• 保留指数：
  1838.9;1835.1;1833.9

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  62.7
• 氢给体数：
  2
• 氢受体数：
  5

ADMET

代谢

CYPRAZINE迅速在耐受玉米、高粱和甘蔗的叶子中被代谢成水溶性化合物，而在易感大麦中代谢较慢，通过谷胱甘肽或γ-谷氨酰半胱氨酸取代2-氯基团。产生的硫醚结合物是在处理6小时后存在的水溶性代谢物中含量最丰富的。

CYPRAZINE WAS RAPIDLY METABOLIZED TO WATER SOL CMPD IN LEAVES OF TOLERANT CORN, SORGHUM, & SUGAR CANE & MORE SLOWLY IN SUSCEPTIBLE BARLEY, BY DISPLACEMENT OF 2-CHLORO GROUP BY GLUTATHIONE OR GAMMA-GLUTAMYLCYSTEINE. THE RESULTING SULFIDE CONJUGATES WERE AMONG THE MOST ABUNDANT WATER SOL METABOLITES PRESENT 6 HR AFTER TREATMENT.

来源:Hazardous Substances Data Bank (HSDB)

代谢

氯三嗪类化合物与植物酶反应，这些酶负责它们的共轭作用，按GS-13529、阿特拉津、环丙津、丙帕津和西玛津的顺序递减，这与它们的水溶性或分配系数无关。显然，C4和C6位置上的完整烷氨基取代基是共轭作用的优选结构，因为当侧链烷基团中的一个被移除时，大部分酶活性丧失。

CHLOROTRIAZINES REACTED /WITH A PLANT ENZYME RESPONSIBLE FOR THEIR CONJUGATION/ IN THE DECREASING ORDER OF GS-13529, ATRAZINE, CYPROZINE, PROPAZINE, & SIMAZINE WITH NO CORRELATION TO THEIR WATER SOLUBILITY OR PARTITION COEFFICIENTS. APPARENTLY, INTACT ALKYLAMINO SUBSTITUENTS @ BOTH C4 & C6 POSITIONS ARE PREFERRED STRUCTURES FOR CONJUGATION SINCE MOST OF THE ENZYME ACTIVITY WAS LOST WHEN ONE OF THE SIDE CHAIN ALKYL GROUPS WAS REMOVED.

来源:Hazardous Substances Data Bank (HSDB)

代谢

在玉米中，观察到叶面施用的赛普罗辛迅速结合，但在3周的过程中急剧下降。在那时，羟基衍生物的浓度增加到与结合物相同的水平。

IN CORN, RAPID CONJUGATION OF FOLIARLY APPLIED CYPROZINE ... WAS OBSERVED, BUT DECR DRASTICALLY IN COURSE OF 3 WK. AT THAT TIME THE INCR HYDROXY DERIVATIVES REACHED CONCN OF THE CONJUGATES.

来源:Hazardous Substances Data Bank (HSDB)

代谢

在大鼠中给予单次口服剂量的（14）碳标记的氯氮平后，鉴定出四种尿液代谢物：2-羟基-4,6-二氨基-S-三嗪；2-氯-4,6-二氨基-S-三嗪；2-羟基-4-氨基-6-异丙氨基-S-三嗪；以及2-氯-4-氨基-6-异丙氨基-S-三嗪。

IN RATS ADMIN SINGLE ORAL DOSES OF (14)CARBON LABELED CYPRAZINE, FOUR URINARY METABOLITES WERE IDENTIFIED: 2-HYDROXY-4,6-DIAMINO-S-TRIAZINE; 2-CHLORO-4,6-DIAMINO-S-TRIAZINE; 2-HYDROXY-4-AMINO-6-ISOPROPYLAMINO-S-TRIAZINE; & 2-CHLORO-4-AMINO-6-ISOPROPYLAMINO-S-TRIAZINE.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 医疗监测

初步医疗检查以检测中枢神经系统、肝脏、心脏、肾脏、肺和皮肤的慢性疾病，以及内分泌或免疫系统的紊乱，应该……/保护/易感个体。……定期对内部器官、皮肤和眼睛进行医疗检查，以避免慢性职业中毒。如果需要，应包括实验室测试和贴片测试。/除草剂/

Preliminary medical exam to detect chronic diseases of CNS, liver, heart, kidneys, lung & skin, as well as endocrinological or immunological disturbances, should ... /protect/ susceptible individuals. ... Periodical medical exam of internal organs, skin & eyes is important to avoid chronic occupational intoxications. It should include lab tests & patch tests if necessary. /Herbicides/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

亚急性毒性（口服摄入）：A. 技术材料 (1) 白化大鼠 90 天，4 至 50 毫克/千克/天，无有害影响。 (2) 比格犬 90 天，2.5 毫克/千克/天，无有害影响；12.5 毫克/千克/天，雄性比格犬体重增长受抑制；雌性比格犬不受影响。 (3) 比格犬 18 天，50 毫克/千克/天，频繁呕吐和腹泻；小肠充血。

SUBACUTE TOXICITY (ORAL INGESTION): A. TECHNICAL MATERIAL (1) ALBINO RATS 90 DAYS, 4 TO 50 MG/KG/DAY, NO DELETERIOUS EFFECTS. (2) BEAGLE DOGS, 90 DAYS, 2.5 MG/KG/DAY, NO DELETERIOUS EFFECTS; 12.5 MG/KG/DAY, DEPRESSED WT GAIN IN MALE BEAGLES; FEMALE BEAGLES NOT AFFECTED. (3) BEAGLE DOGS 18 DAYS, 50 MG/KG/DAY, FREQUENT VOMITING & DIARRHEA; HYPEREMIA OF SMALL INTESTINE.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

A. 皮肤 (1) 可乳化浓缩物 (1磅活性成分/加仑) 荷兰带状兔 (荷兰带状品系) 在单次24小时期间暴露于未稀释的乳化浓缩物，剂量为1.0-4.0毫升/公斤，对兔皮肤有中等刺激性。14天后皮肤恢复正常。 B. 眼睛 (1) 可乳化浓缩物 (1磅活性成分/加仑)。未稀释的乳化浓缩物对兔眼（新西兰品系）有轻度刺激性。刺激症状在单次暴露后5-7天内消失。 C. 吸入 (1) 可乳化浓缩物 (1磅活性成分/加仑)。将大鼠单次暴露于1小时的乳化浓缩物气溶胶（用二甲苯稀释）@浓度为1.8和7.78毫克乳化浓缩物/升空气，暴露后14天进行尸检得到以下信息：1.78毫克/升 - 尸检未观察到药理或毒理迹象。7.78毫克/升 - 10只大鼠中有3只肺部含有许多小脓肿。

A. SKIN (1) EMULSIFIABLE CONCENTRATE (1 LB AI/GAL) FEMALE RABBITS (DUTCH BELTED STRAIN) WERE EXPOSED FOR SINGLE 24 HR PERIOD TO UNDILUTED EMULSIFIABLE CONCENTRATE DOSES OF 1.0-4.0 ML/KG WERE MODERATELY IRRITATING TO RABBIT SKIN. SKIN WAS NORMAL @ END OF 14 DAYS. B. EYES (1) EMULSIFIABLE CONCENTRATE (1 LB AI/GAL). UNDILUTED EMULSIFIABLE CONCENTRATE WAS FOUND TO BE MILDLY IRRITATING TO RABBIT EYES (NEW ZEALAND STRAIN). SIGNS OF IRRITATION DISAPPEARED IN 5-7 DAYS FOLLOWING A SINGLE EXPOSURE. C. INHALATION (1) EMULSIFIABLE CONCENTRATE (1 LB AI/GAL). SINGLE 1 HR EXPOSURE OF RATS TO AEROSOLS OF THE EMULSIFIABLE CONCENTRATION (DILUTED WITH XYLENE) @ CONCN OF 1.8 & 7.78 MG EMULSIFIABLE CONCENTRATION /l OF AIR YIELDED FOLLOWING INFORMATION ON AUTOPSY 14 DAYS POST EXPOSURE: 1.78 MG/l- NO PHARMACOLOGICAL OR TOXICOLOGICAL SIGNS WERE OBSERVED ON AUTOPSY. 7.78 MG/L- 3 OUT OF 10 RATS HAD LUNGS CONTAINING NUMEROUS SMALL ABSCESSES.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

塞普拉嗪、阿特拉嗪和西玛嗪在4种沙门氏菌测试株（TA98、TA100、TA1535和TA1538）中，在每块平板上最多100微克的浓度下，并且在存在阿罗氯诱导的S9的情况下，并未表现出致突变性。

CYPRAZINE, ATRAZINE & SIMAZINE WERE NOT MUTAGENIC IN 4 SALMONELLA TESTER STRAINS (TA98, TA100, TA1535, AND TA1538) AT UP 100 UG/PLATE IN PRESENCE OF AROCHLOR-INDUCED S9.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

/TRIAZINES/ ... 可能通过叶面吸收或土壤施用或两者兼而有之发挥活性。更广泛的活性似乎是通过土壤吸收发生的，而叶面活性化合物 ... 的活性往往仅限于简单的一年生植物，或者仅仅是对多年生植物的叶面杀灭。 /TRIAZINES/

/TRIAZINES/ ... MAY EXERT ACTIVITY VIA EITHER FOLIAR UPTAKE OR SOIL APPLICATION OR BOTH. BROADER ACTIVITY APPEARS TO OCCUR VIA SOIL UPTAKE, WHILE THE FOLIAR ACTIVE CMPD ... TEND TO BE LIMITED IN THEIR ACTIVITY TO THE SIMPLE ANNUALS OR MERELY TO FOLIAGE KILL OF PERENNIALS. /TRIAZINES/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

叶片和根部吸收在植物中都发生。化学物质向上运输，但不向下运输。

BOTH FOLIAR & ROOT ABSORPTION OCCUR /IN PLANTS/. ... CHEMICAL MOVES ACROPETALLY BUT NOT BASIPETALLY.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

实验大鼠单次口服给药(14)碳标记的氯丙嗪后，72小时内(14)碳标记的氯丙嗪的放射性物质97.6%被排出体外（其中72.7%通过尿液排出，24.9%通过粪便排出）。呼出的气体中，放射性二氧化碳（14）的检测量不到1%。在大鼠处死时，即给药后72小时，其体内还含有7.5%的放射性物质。

RATS ADMIN SINGLE ORAL DOSES OF (14)CARBON-LABELED CYPRAZINE EXCRETED 97.6% WITHIN 72 HR (72.7% IN URINE & 24.9% IN FECES). LESS THAN 1% OF RADIOACTIVITY WAS DETECTED IN EXPIRED AIR AS (14)CARBON DIOXIDE. RATS CONTAINED 7.5% OF RADIOACTIVITY @ SACRIFICE, 72 HR AFTER DOSING.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 海关编码：
  2933699011

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: 1200毫克/公斤
可燃性危险特性：燃烧产生有毒氮氧化物和氯化物气体
储运特性：库房通风低温干燥，与食品原料分开储运
灭火剂：干粉、泡沫、砂土
职业标准：TLV-TWA 5毫克/立方米

反应信息

• 作为反应物：
  描述：

  2-butoxycarbonylsulfenyl chloride 、 环丙津 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以29%的产率得到Butan-2-yl [[4-chloro-6-(propan-2-ylamino)-1,3,5-triazin-2-yl]-cyclopropylamino]sulfanylformate
  参考文献：
  名称：

  Pilgram, K. H.; Gale, Laird H., Journal of Heterocyclic Chemistry, 1988, vol. 25, p. 193 - 200

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4-二氯-6-异丙基氨基-1,3,5-三嗪 、 环丙胺 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 环丙津
  参考文献：
  名称：

  Selective NPY (Y5) antagonists (triazines)

  摘要：

  这项发明涉及选择性拮抗剂，用于NPY（Y5）受体的三嗪衍生物。该发明提供了一种包含本发明化合物的治疗有效量和药用可接受载体的药物组合物。该发明提供了一种由本发明化合物的治疗有效量和药用可接受载体组合而成的药物组合物。此外，该发明还提供了一种制备药物组合物的方法，包括将本发明化合物的治疗有效量与药用可接受载体组合。

  公开号：

  US06340683B1

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