基本情報
- CAS
70630-17-0- 標準SMILES
COCC(=O)N(c1c(C)cccc1C)[C@H](C)C(=O)OC- InChIKey
ZQEIXNIJLIKNTD-GFCCVEGCSA-N- 分子式
- C15H21NO4
- 平均分子量
- 279.33 g/mol
- 単同位体質量
- 279.14705815
概要
Metalaxyl-M is a methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate that is the more active R-enantiomer of metalaxyl. A systemic fungicide, it is active against phytopathogens of the order Peronosporales and is used to conrtrol Pythium in a number of vegetable crops. It has a role as an agrochemical. It is a methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate, a D-alanine derivative, an acylamino acid fungicide and an anilide fungicide. It is functionally related to a D-alanine. It is an enantiomer of a (S)-metalaxyl.
名称と識別子
- 優先名称
- (R)-Metalaxyl
- IUPAC
- methyl (2R)-2-(N-(2-methoxyacetyl)-2,6-dimethylanilino)propanoate
- 現地名
- N-(2,6-ジメチルフェニル)-N-(メトキシアセチル)-D-アラニンメチル
- 英語名
- Metalaxyl-M
- 分子式
- C15H21NO4
- 分子量
- 279.33
名称と別名
Metalaxyl-MMefenoxam70630-17-0(-)-MetalaxylRidomil Gold(R)-MetalaxylMethyl N-(methoxyacetyl)-N-(2,6-xylyl)-D-alaninateF1Q54ONN4Hmethyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-D-alaninateDTXSID8032671D-Alanine, N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-, methyl esterDTXCID6012671
名称をさらに表示
(R)-2-[N-(2,6-ジメチルフェニル)-N-メトキシアセチルアミノ]プロパン酸メチルN-(2,6-ジメチルフェニル)-N-(メトキシアセチル)-D-アラニンメチル(R)-メタラキシル(R)-2-[N-(2,6-ジメチルフェニル)-N-(メトキシアセチル)アミノ]プロピオン酸メチルメフェノキサムN-(2-メトキシアセチル)-N-(2,6-ジメチルフェニル)-D-アラニンメチルメタラキシルMメタラキシル-M標準品メタラキシル‐M標準品メフェノキサムメタラキシル-Mメタラキシル-M標準物質メタラキシル-Mサブデューマックスメチル (2R)-2-[N-(2,6-ジメチルフェニル)-2-メトキシアセトアミド]プロパノアートリドミルゴールドメフェノキサム標準品METALAXIL-M(R)-2-{(2,6-Dimethylphenylmethoxy)acetylamino}-propionic acid methyl ester
物性
構造計算による物性
- XLogP
- 1.6
- 極性表面積
- 55.8 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 4
- 回転可能結合数
- 6
- 重原子数
- 20
- 形式電荷
- 0
- 複雑度
- 335
実験および物理化学的性質
Pesticides
Agrochemicals -> Pesticide active substances
Active substance -> EU Pesticides database: Approved
Environmental transformation -> Pesticides (parent, predecessor)
Collision Cross Section168.8 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID8032671]
物理化学的性質
- 融点
- -38.6 °C · -38.6°C
- 沸点
- 422.1 °C · 422.1°C (rough estimate)
- 比重(密度)
- 1.1083 · 1.1083 (rough estimate)
- 屈折率
- 1.513 · 1.5130 (estimate)
- 貯蔵温度
- 0 · 0-6°C
- 溶解性
- Chloroform (Slightly), Methanol (Slightly)
- 酸解離定数(Pka)
- 1.41 · 1.41±0.50(Predicted)
- 外見
- Viscous Liquid
- 色
- Colorless to light yellow
- Henry's Law Constant
- 2.8 · 2.8×104 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
- 主な用途
- 農業環境
- InChI
- 1S/C15H21NO4/c1-10-7-6-8-11(2)14(10)16(13(17)9-19-4)12(3)15(18)20-5/h6-8,12H,9H2,1-5H3/t12-/m1/s1
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
Danger
H302: Harmful if swallowed [Warning Acute toxicity, oral]
P264, P264+P265, P270, P280, P301+P317, P305+P354+P338, P317, P330, and P501 (click each P-code to see the statement)
Danger
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P264+P265, P270, P280, P301+P317, P305+P354+P338, P317, P330, and P501 (click each P-code to see the statement)
危険有害性情報
Regulatory Information
Regulation (EC) No 396/2005 (amended)
Mefenoxam is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)
02/64/EC, 2010/77/EU, Reg (EU) 2026/1353, Reg. (EU) 2015/1885, Reg. (EU) 2016/549, Reg. (EU) 2017/841, Reg. (EU) 2018/917, Reg. (EU) 2019/707, Reg. (EU) 2020/617, Reg. (EU) 2024/1718, Reg. (EU) No 540/2011
Metalaxyl-m: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazard Classes and Categories
Acute Tox. 4 (100%)
Acute toxicity - category 4
Acute Tox. 4 *
毒性情報
Treatment
Consider gastric lavage, as well was dilution with milk or water after ingestion. Administer charcoal as a slurry following ingestion; however, activated charcoal should not be given to patients ingesting strong acidic or basic caustic chemicals. In case of inhalation, move patient to fresh air. Monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. Irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. Following dermal exposure, remove contaminated clothing and wash exposed area thoroughly with soap and water. Treat dermal irritation or burns with standard topical therapy. Patients developing dermal hypersensitivity reactions may require treatment with systemic or topical corticosteroids or antihistamines. Administer symptomatic treatment as necessary. (T36)
化学と産業
薬理情報
Metabolism/Metabolites
Three major and one minor metabolic pathways are proposed. One pathway involves hydrolysis of the ether, followed by oxidation of the resulting alcohol, ester hydrolysis, or N-dealkylation of the ester chain. A second pathway involves oxidation of an aromatic methyl to the benzylic acid or ester hydrolysis. The third major pathway is ester hydrolysis, sometimes followed by benzylic acid formation. The minor pathway involves hydroxylation at the meta position of the phenyl ring. The majority of urinary metabolites are conjugated (glucuronide or sulfate) whereas fecal metabolites are mostly unconjugated. The major metabolite in urine & feces is N-(2,6-dimethylphenyl)-N-(hydroxyacetyl) alanine. Metalaxyl is excreted in urine and the feces. (L918)
用途と製造
UsesWidely used selective herbicide worldwide in corn, soybean and other crop cultures. Elevated concentrations of this herbicide and its degradation products have been detected in surface and groundwater. (A252)
Household ProductsInformation on 2 consumer products that contain Metalaxyl-M in the following categories is provided:
Use ClassificationEnvironmental transformation -> Pesticides (parent, predecessor)
応用分野
用途RNAポリメラーゼI阻害剤ブドウのべと病やジャガイモの疫病など卵菌類による病害に対して有効
説明Metalaxyl-M is the more active of the two enantiomers of the phenylamide fungicide metalaxyl; metalaxyl is currently registered in more than 80 countries with uses on more than 60 crops. 1996 Mefenoxam (metalaxyl-M) first registered for use in NYS. Metalaxyl-M is the first enantiomeric form of a fungicide introduced into the market. When used as seed-treatment, soil treatment or foliar application against fungi of the order Peronosporales, it provides the same excellent level of efficacy as metalaxyl but at half the application rate. Mefenoxam is more commonly used than metalaxyl in most pesticide products registered in NYS today.
関連反応
2 件
化合物ノート
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