嘧霉胺 | 53112-28-0

• 物质功能分类: 化学农药原药 - 杀菌剂 - 其他杀菌剂
• 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: 嘧霉胺
• 中文别名: 嘧螨醚；棉胺宁；2-苯胺-4,6-二甲基嘧啶；N-(4,6-二甲基嘧啶-2-基)苯胺；4,6-二甲基-N-苯基-2-嘧啶胺；施佳乐；N－(4,6-二甲基嘧啶-2-基) 苯胺；二甲基嘧啶胺
• 英文名称: Pyrimethanil
• 英文别名: 4,6-dimethyl-N-phenylpyrimidin-2-amine
• CAS: 53112-28-0
• 化学式: C₁₂H₁₃N₃
• mdl: MFCD00172113
• 分子量: 199.255
• InChiKey: ZLIBICFPKPWGIZ-UHFFFAOYSA-N

物化性质

• 熔点：
  96°C
• 沸点：
  362.8±45.0 °C(Predicted)
• 密度：
  1.15
• 溶解度：
  二甲基亚砜：130 mg/mL（652.45 mM）
• 物理描述：
  Solid
• 颜色/状态：
  Colorless crystals
• 蒸汽压力：
  1.65X10-5 mm Hg @ 25 °C
• 稳定性/保质期：
  如果按照规格使用和储存，则不会分解，没有已知的危险反应。
• 解离常数：
  pKa (conjugate acid)= 3.52
• 碰撞截面：
  142.95 Ų [M+H]+ [CCS Type: TW]
• 保留指数：
  1762.4

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  37.8
• 氢给体数：
  1
• 氢受体数：
  3

ADMET

代谢

代谢涉及氧化成羟基衍生物然后进行结合。...在水果上发生的代谢很少。

Metabolism involves oxidation to hydroxylated derivatives followed by conjugation. ... Little metabolism occurs on fruit.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

癌症分类：C组可能的人类致癌物

Cancer Classification: Group C Possible Human Carcinogen

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌物分类

对人类无致癌性（未列入国际癌症研究机构IARC清单）。

No indication of carcinogenicity to humans (not listed by IARC).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 副作用

职业性肝毒素 - 第二性肝毒素：在职业环境中的毒性效应潜力是基于人类摄入或动物实验的中毒案例。

Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.

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

毒理性

• 人类毒性摘录

碱性彗星试验用于评估农民在正常条件下使用选定农药进行1天喷洒前后单核白细胞的DNA损伤。收集了两个血液样本，一个在喷洒当天上午（S0），第二个在喷洒后次日早上（S1）。在这里，我们评估了这两个采样时间之间DNA损伤水平的变化。根据暴露情况，形成了四组农民：(a) 各种杀菌剂-杀虫剂混合物（包括百菌清；第1组，n = 8），(b) 杀草剂异丙隆（第2组，n = 11），(c) 杀菌剂三唑（第3组，n = 14），和(d) 杀菌剂（百菌清）-杀虫剂混合物（第4组，n = 8）。观察到S1时，第1组和第4组（暴露于相似农药）的DNA损伤水平增加。这种增加与S0和S1之间喷洒的区域以及在这1天期间使用的喷洒罐数量有关。对于这两组，没有观察到对细胞活力或血液学参数的影响。当每组作为一个整体观察时，没有观察到喷洒后次日DNA损伤水平有统计学上的显著变化。然而，一些农民在暴露后DNA损伤显著增加，而其他农民损伤减少。在这两组中，观察到S1时中性粒细胞显著减少，第3组观察到红细胞减少。与此同时，这两组观察到淋巴细胞的活力显著下降。1天的喷洒期似乎足以显著改变单核白细胞的DNA损伤水平，但这一变化与农药相关暴露参数的相关性取决于所涉及的农药种类。

The alkaline comet assay was used to assess DNA damage in mononuclear leukocytes of farmers before and after a 1-day spraying period with selected pesticides under usual conditions. Two blood samples were collected, one in the morning of the day of spraying (S0) and the second in the morning of the day after (S1). Here, we assessed variations in DNA damage levels between these two sampling times. Four groups of farmers were formed, according to exposure to: (a) various fungicide-insecticide mixtures (including chlorothalonil; group 1, n = 8), (b) the herbicide isoproturon (group 2, n = 11), (c) fungicide triazoles (group 3, n = 14), and (d) a fungicide (chlorothalonil)-insecticide mixture (group 4, n = 8). An increase in DNA damage levels was observed at S1 for groups 1 and 4, who were exposed to similar pesticides. This increase was correlated with area sprayed between S0 and S1 and with the number of spraying tanks used over this 1-day period. No effect was observed on cell viability or on hematological parameters for these two groups. No statistically significant modification of DNA damage level was observed the day after spraying for groups 2 and 3, when each was observed as a whole. However, some farmers presented significantly more DNA damage after exposure, and others presented less damage. In these two groups, a significant decrease of neutrophils was observed at S1, and a decrease of red blood cells was observed in group 3. In parallel, a significant loss of lymphocyte viability was observed in these two groups. A 1-day spraying period seems to be sufficient to significantly modify DNA damage levels in mononuclear leukocytes, but the correlation of this change with pesticide-related exposure parameters depends on the kind of pesticide concerned.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

在封闭系统中，当相对湿度大于或等于80%时，可能对敏感植物种类（例如茄科植物）产生植物毒性。

May be phytotoxic in closed systems at >/= 80% relative humidity on sensitive species (e.g. Solanaceae).

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

在大鼠中，该物质会被迅速吸收、代谢和排泄。在单次口服给药后，6-8小时内会有超过95%被排泄。

In the rat, rapidly absorbed, metabolized and excreted. Following single oral dose, > 95% excreted within 6-8 hours.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险品标志：
  N
• 安全说明：
  S60
• 危险类别码：
  R51/53
• WGK Germany：
  2
• 危险品运输编号：
  UN 3077
• 海关编码：
  2942000000
• 储存条件：
  密封，在0-6°C下保存

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: Pyrimethanil
Synonyms:

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

---

Section 3. Composition/information on ingredients.
Ingredient name: Pyrimethanil
CAS number: 53112-28-0

---

Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

---

Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

---

Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

---

Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

---

Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

---

Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C12H13N3
Molecular weight: 199.3

---

Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

嘧霉胺 介绍

嘧霉胺（Thiophanate-methyl）是一种广泛使用的杀菌剂，主要针对多种作物上的灰霉病、枯萎病以及果树黑星病、斑点落叶病等。

合成方法

嘧霉胺的合成主要有四种途径：

1. 以脲和乙酰丙酮为起始原料：通过两步反应得到目标化合物。
2. 以硫脲为起始原料，经过甲基化、氧化、取代及水解等一系列步骤制备。
3. 以硫脲为起始原料，经甲基化、取代和合环最终合成。
4. 以苯胺和氨基氰作为原料，通过加成反应、取代及合环完成合成。

物理化学性质

• 原药呈现白色结晶粉末状，熔点约为93.3℃。
• 在水中溶解度为0.121g/L（25℃），蒸汽压为2.2mPa。
• 油水分配系数(logP)在一定pH值范围内较为稳定。

生态和毒理学 人类毒性

• 对大鼠吸入LC50（4h）>1.98 mg/L，口服LD50无明确数据。
• 野鸭、山齿鹑及镜鲤等动物急性经口LD50和LC50均大于阈值；蜜蜂接触LD50 >100 μm/只。

生态学

• 对非靶标节肢动物影响较小，对水生生物（如水蚤）有较高毒性。
• 未显示致突变、畸变作用或遗传毒性。

应用与防治对象

• 作物：适用于韭菜、黄瓜、番茄、葡萄、草莓、豌豆等。
• 施用量：
  • 防治葡萄灰霉病（葡萄孢菌）：500~1,000 g/hm²；
  • 防治草莓灰霉病：800~1,000 g/hm²；
  • 防治黄瓜、韭菜灰霉病，施药量分别为40%嘧霉胺的80-95 mL/亩和50-75 mL/亩。
• 用途：
  • 观赏植物（如观赏菊花）：使用80%嘧霉胺1,000~2,000倍液喷雾；
  • 果树黑星病、斑点落叶病等。

化学性质

• 原药能溶于大多数有机溶剂，且在特定pH值下较为稳定。
• 在玻璃和塑料大棚内施用时需注意相对湿度大于80%并安装通风设备以避免某些作物出现叶斑问题。

反应信息

• 作为反应物：
  描述：

  嘧霉胺 在 pyridinium chlorochromate 作用下， 以 溶剂黄146 为溶剂， 反应 0.08h， 以79.4%的产率得到5-bromo-4,6-dimethyl-N-phenylpyrimidin-2-amine
  参考文献：
  名称：

  一些新的苯胺基嘧啶衍生物的合成和杀真菌作用评价

  摘要：

  合成了一系列新的苯胺基嘧啶和嘧啶并[4,5- c ] a庚因衍生物，以评估其体外抗真菌活性。N-乙酰苯胺基嘧啶衍生物7与参考杀真菌剂嘧菌胺2相比，对黑曲霉表现出相似的杀真菌活性。此外，与杀真菌剂2（12 h的2.5μg/ ml ）相比，它的破裂时间更短（9 h时为2.5μg/ ml）。溴化嘧啶衍生物5具有比氰基衍生物6和6-溴代烷基类似物4更高的杀真菌活性。熔融嘧啶基[4,5- c] a庚因衍生物10对黑曲霉的活性较低。研究了溴化铬酸吡啶鎓作为选择性溴化剂在嘧啶环而不是在侧链甲基上的新应用。

  DOI：

  10.1007/s00044-013-0535-2
• 作为产物：
  描述：

  4,6-二甲基-1-苯基嘧啶-2-硫酮 在 镍 sodium hydroxide 、 盐酸羟胺 、 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 2.0h， 生成 嘧霉胺
  参考文献：
  名称：

  Kashima, Choji; Katoh, Akira; Yokota, Yuko, Chemical and pharmaceutical bulletin, 1981, vol. 29, # 9, p. 2516 - 2519

  摘要：

  DOI：

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] BICYCLYL-SUBSTITUTED ISOTHIAZOLINE COMPOUNDS<br/>[FR] COMPOSÉS ISOTHIAZOLINE SUBSTITUÉS PAR UN BICYCLYLE
  申请人：BASF SE

  公开号：WO2014206910A1

  公开（公告）日：2014-12-31

  The present invention relates to bicyclyl-substituted isothiazoline compounds of formula (I) wherein the variables are as defined in the claims and description. The compounds are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes. The invention also relates to a method for controlling invertebrate pests by using these compounds and to plant propagation material and to an agricultural and a veterinary composition comprising said compounds.

  本发明涉及公式（I）中变量如索权和说明中所定义的自行车基取代异噻唑啉化合物。这些化合物对抗或控制无脊椎动物害虫，特别是节肢动物害虫和线虫方面具有用途。该发明还涉及一种通过使用这些化合物来控制无脊椎动物害虫的方法，以及包含所述化合物的植物繁殖材料、农业和兽医组合物。
• [EN] AZOLINE COMPOUNDS<br/>[FR] COMPOSÉS AZOLINE
  申请人：BASF SE

  公开号：WO2015128358A1

  公开（公告）日：2015-09-03

  The present invention relates to azoline compounds of formula (I) wherein A, B1, B2, B3, G1, G2, X1, R1, R3a, R3b, Rg1 and Rg2 are as defined in the claims and the description. The compounds are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes. The invention also relates to a method for controlling invertebrate pests by using these compounds and to plant propagation material and to an agricultural and a veterinary composition comprising said compounds.

  本发明涉及式（I）的噁唑啉化合物，其中A、B1、B2、B3、G1、G2、X1、R1、R3a、R3b、Rg1和Rg2如权利要求和描述中所定义。这些化合物对抗或控制无脊椎动物害虫，特别是节肢动物害虫和线虫方面具有用途。该发明还涉及一种利用这些化合物控制无脊椎动物害虫的方法，以及包括所述化合物的植物繁殖材料、农业和兽医组合物。
• [EN] SUBSTITUTED QUINAZOLINES AS FUNGICIDES<br/>[FR] QUINAZOLINES SUBSTITUÉES, UTILISÉES EN TANT QUE FONGICIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2010136475A1

  公开（公告）日：2010-12-02

  The present invention relates to a compound of formula (I) wherein wherein the substituents have the definitions as defined in claim 1or a salt or a N-oxide thereof, their use and methods for the control and/or prevention of microbial infection, particularly fungal infection, in plants and to processes for the preparation of these compounds.

  本发明涉及一种具有如下式（I）的化合物，其中取代基具有权利要求1中定义的定义，或其盐或N-氧化物，它们的用途以及用于控制和/或预防植物中微生物感染，特别是真菌感染的方法，以及制备这些化合物的方法。
• [EN] MICROBIOCIDAL OXADIAZOLE DERIVATIVES<br/>[FR] DÉRIVÉS D'OXADIAZOLE MICROBIOCIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2017157962A1

  公开（公告）日：2017-09-21

  Compounds of the formula (I) wherein the substituents are as defined in claim 1, useful as a pesticides, especially fungicides.

  式(I)的化合物，其中取代基如权利要求1所定义，作为杀虫剂特别是杀菌剂有用。