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(3,4-ジエトキシフェニル)カルバミド酸イソプロピル

Diethofencarb

HCID 91742
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
87130-20-9
標準SMILES
CCOc1ccc(NC(=O)OC(C)C)cc1OCC
InChIKey
LNJNFVJKDJYTEU-UHFFFAOYSA-N
分子式
C14H21NO4
平均分子量
267.32 g/mol
単同位体質量
267.14705815

概要

Diethofencarb is a carbamate ester that is the isopropyl ester of (3,4-diethoxyphenyl)carbamic acid. A fungicide with strong activity against Botrytis cinerea and benzimidazole-resistant strains of Botryis spp. It has a role as an antifungal agrochemical. It is a carbamate ester, an aromatic ether and a carbanilate fungicide. It is functionally related to an aniline.

名称と識別子

優先名称
Diethofencarb
IUPAC
propan-2-yl N-(3,4-diethoxyphenyl)carbamate
現地名
(3,4-ジエトキシフェニル)カルバミド酸イソプロピル
英語名
Diethofencarb
分子式
C14H21NO4
分子量
267.32

名称と別名

Diethofencarb87130-20-9Isopropyl 3,4-diethoxycarbanilatePowmyl WPpropan-2-yl N-(3,4-diethoxyphenyl)carbamateDTXSID5037527Isopropyl N-(3,4-diethoxyphenyl)carbamate1-Methylethyl (3,4-diethoxyphenyl)carbamateIsopropyl 3,4-diethoxyphenylcarbamate421BLT77U4CHEBI:4520DTXCID3017527
名称をさらに表示
ジエトフェンカルブパウミルN-(3,4-ジエトキシフェニル)カルバミド酸イソプロピル3,4-ジエトキシフェニルカルバミド酸イソプロピル(3,4-ジエトキシフェニル)カルバミン酸イソプロピル(3,4-ジエトキシフェニル)カルバミド酸イソプロピルN-(3,4-ジエトキシフェニル)カルバミン酸イソプロピルイソプロピル3,4-ジエトキシカルバニラートジエトフェンカルブ標準品イソプロピル3,4ジエトキシカルバニラトプロパン-2-イル N-(3,4-ジエトキシフェニル)カルバマートs-165s-1605s32165powmylwpBiethofencarbDegarelix Impurity 11Diethofencarb PESTANAL
1-methylethyl N-(3,4-diethoxyphenyl)carbamateCarbamic acid, (3,4-diethoxyphenyl)-, 1-methylethyl esterisopropyl-3,4-diethoxycarbanilateRefChem:586957powmilDiethofenacarbDiethofencarb [ISO]Isopropyl (3,4-diethoxyphenyl)carbamate

物性

構造計算による物性補完中

XLogP
2.8
極性表面積
56.8 Ų
水素結合供与体数
1
水素結合受容体数
4
回転可能結合数
7
重原子数
19
形式電荷
0
複雑度
270

実験および物理化学的性質

Pesticides · 5 件

Fungicides

Active substance -> EU Pesticides database: Not approved

Fungicides

Environmental transformation -> Pesticides (parent, predecessor)

Pesticide (Diethofencarb) -> USDA PDB

LogP2.82
Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section171.9 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID5037527]

物理化学的性質

融点
101.3 ° · 101.3°
沸点
325.9 · 325.9±32.0 °C(Predicted)
比重(密度)
1.098 · 1.098±0.06 g/cm3(Predicted)
蒸気圧
8.4 x · 8.4 x 10-3 Pa (20 °C)
貯蔵温度
2 · 2-8°C
溶解性
クロロホルム(微量)、酢酸エチル(微量)
水溶解度
26.6 mg · 26.6 mg l-1 (20 °C)
酸解離定数(Pka)
12.75 · 12.75±0.70(Predicted)
色
淡いピンク~淡いピンク

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

Warning

H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)

Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory.

Warning

H319 (97%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

危険有害性情報

Regulatory Information · 3 件

Commission Regulation (EC) No 1490/2002

Diethofencarb is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

2011/26/EU, Reg. (EU) 2022/801, Reg. (EU) No 540/2011

Hazard Classes and Categories · 2 件

Eye Irrit. 2 (97%)

Eye Irrit. 2 (100%)

毒性情報

Treatment · 1 件

If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.

Health Effects · 1 件

化学と産業

薬理情報

Metabolism/MetabolitesThe carbamates are hydrolyzed enzymatically by the liver; degradation products are excreted by the kidneys and the liver. (L793)

用途と製造

UsesDiethofencarb is widely used as an insecticide or pesticide in homes, gardens and agricultural applications. It is a synthetic compound.
Use Classification · 2 件

Fungicides

Environmental transformation -> Pesticides (parent, predecessor)

応用分野 · 2 件

用途ジエトフェンカルブ試験用標準品。

使用Diethofencarb is a systemic carbamate fungicide with both protective and curative activities used for the control especially of benzimidazole-resistant strains of fungi, including Botrytis spp., Cercosporu spp. and Venturia spp. It is almost ineffective against benzimidazole- susceptible strains. It is used on vines, cucurbits, tomatoes, citrus, vegetables and other crops.

上流・下流製品情報

下流製品

(3,4-ジエトキシフェニル)カルバミド酸プロピル

補足説明

定義ChEBI: A carbamate ester that is the isopropyl ester of (3,4-diethoxyphenyl)carbamic acid. A fungicide with strong activity against Botrytis cinerea and benzimidazole-resistant strains of Botryis spp.

関連反応

3 件
反応記録を作成
HRID 365116 の反応式
HRID 365116生成物としてuspto-grants-1986_08
HRID 365118 の反応式
HRID 365118反応物としてuspto-grants-1986_08
HRID 806194 の反応式
HRID 806194反応物としてTest data from https://doi.org/10.1039/C8SC04228D

化合物ノート

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データベース識別子

CAS
87130-20-9
PubChem CID
91742
DTXSID
DTXSID5037527
ChEMBL
CHEMBL1079613、CHEMBL1880404
ChEBI
CHEBI:4520
UNII
421BLT77U4
EC Number
403-870-3、617-968-0
Nikkaji
J135.062E
Henry's Law Constant
1.2 · 1.2×101 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
主な用途
農業環境
InChI
InChI=1S/C14H21NO4/c1-5-17-12-8-7-11(9-13(12)18-6-2)15-14(16)19-10(3)4/h7-10H,5-6H2,1-4H3,(H,15,16)
InChIKey
LNJNFVJKDJYTEU-UHFFFAOYSA-N
SMILES
C(OC(C)C)(=O)NC1=CC=C(OCC)C(OCC)=C1
LogP
2.91 · 2.910
CAS データベース
87130 · 87130-20-9(CAS DataBase Reference)
EPAの化学物質情報
Carbamic acid, N-(3,4-diethoxyphenyl)-, 1-methylethyl ester (87130-20-9)

Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Chronically high (>10 years) exposure leads to neuropsychological consequences including disturbances in perception and visuo-motor processing (A15321).

Exposure RoutesInhalation (L793) ; oral (L793); dermal (L793)
Toxicity Summary · 1 件

Diethofencarb is a cholinesterase or acetylcholinesterase (AChE) inhibitor. Carbamates form unstable complexes with chlolinesterases by carbamoylation of the active sites of the enzymes. This inhibition is reversible. A cholinesterase inhibitor suppresses the action of acetylcholine esterase. Because of its essential function, chemicals that interfere with the action of acetylcholine esterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop.

Signs and Symptoms · 1 件

As with organophosphates, the signs and symptoms are based on excessive cholinergic stimulation. Unlike organophosphate poisoning, carbamate poisonings tend to be of shorter duration because the inhibition of nervous tissue acetylcholinesterase is reversible, and carbamates are more rapidly metabolized. Muscle weakness, dizziness, sweating and slight body discomfort are commonly reported early symptoms. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Contraction of the pupils with blurred vision, incoordination, muscle twitching and slurred speech have been reported. (L795)

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
RAIS Toxicity Values · 2 件

0.5

OPP

EPA Human Health Benchmarks for Pesticides · 5 件

Diethofencarb

0.5

3000

General Population

Human Health Benchmarks for Pesticides - 2021 Update

安全データ

wgk
2
rtecs
EZ4215700
毒性
LD50 in male and female rats (mg/kg): >5000, >5000 orally; >5000, >5000 dermally; LC50 (48 hrs) in carp: 13.5 mg/l; (3 hrs) in Daphnia pulex: >10 mg/l (Fujimura, review)
risk_code
36
hazard_code
Xi
safety_code
26
Hazard Classifications
Eye Irrit. 2
ストレージクラス
11 - Combustible Solids