1-(4-クロロフェノキシ)-3,3-ジメチル-1-(1H-1,2,4-トリアゾール-1-イル)-2-ブタノール
トリアジメノール · 2-(4-クロロフェノキシ)-1-tert-ブチル-2-(1H-1,2,4-トリアゾール-1-イル)エタノール · 1-(4-クロロフェノキシ)-3,3-ジメチル-1-(1H-1,2,4-トリアゾール-1-イル)-2-ブタノール · 1-(1H-1,2,4-トリアゾール-1-イル)-1-(4-クロロフェノキシ)-3,3-ジメチル-2-ブタノール · ベイタン · トリアジメノール標準品 · CS_N-11129-250MG_トリアジメノール · Β-(4-CHLOROPHENOXY)-Α-(1,1-DIMETHYLETHYL)-1H-1,2,4-TRIAZOLE-1-ETHANOL(MIXTURE OF DIASTEREOMERS) (トリアジメノール)
識別子と物理属性
| CAS No. | 55219-65-3 |
|---|---|
| 分子式 | C14H18ClN3O2 |
| 平均分子量 | 295.76 g/mol |
| 単同位体質量 | 295.1087545 g/mol |
| SMILES | CC(C)(C)C(O)C(Oc1ccc(Cl)cc1)n1cncn1 |
| InChIKey | BAZVSMNPJJMILC-UHFFFAOYSA-N |
| PubChem CID | 41368 |
| ChEMBL | CHEMBL520275 |
| ChEBI | CHEBI:9666 |
| EC No. | 259-537-6 |
| DTXSID | DTXSID0032493 |
| 現地名 | 1-(4-クロロフェノキシ)-3,3-ジメチル-1-(1H-1,2,4-トリアゾール-1-イル)-2-ブタノール |
化学・物理的性質
| XLogP | 3.1 |
|---|---|
| 極性表面積 | 60.2 |
| 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 | 5 |
| 重原子数 | 20 |
| 形式電荷 | 0 |
| 複雑度 | 303 |
| LogP（分配係数） | log Kow = 2.90 |
| 臭い | Slight non-specific odor |
| 密度 | 1.22 g/cu cm1.2990 (rough estimate) |
| Color/Form | Colorless crystalline solid |
| 溶解度 | Soluble in alcohol, ketonesIn water, 120 mg/L at 20 °CDMSO（微量）、メタノール（微量）A：62mg・l-1 (20℃)B：33mg・l-1(20℃) |
| Decomposition | When heated to decomposition it emits toxic vapors of /Nitrogen oxides and Chlorides/. |
| 融点 | 118-130 °C112-117° |
| 蒸気圧 | 3.1X10-10 mm Hg at 20 °CA 6 x l0-7 Pa (20 °C)B 4 x l0-7 Pa (20 °C) |
| Physical Description | Solid with a mild non-specific odor[Merck Index] Formulated as emulsifiable, soluble, and flowable concentrates and wettable powder[Reference #1] |
| Kovats Retention Index | 2078.62087.9207620842095208821042065.32063.12064.62069.92079.62062.620502066.72061.92077.120232051.8 |
| Collision Cross Section | 172.08 Ų [M+H]+177.62 Ų [M+Na]+178.1 Ų [M+HCOO]- |
| Other Experimental Properties | Diastereoisomer A(1RS, 2SR) and diastereoisomer B(1RS, 2RS) ratio of A:B is 7:3Diastereoisomer A: MP = 138.2 °CVP = 6X10-4 mPa at 20 °CSG/Density = 1.237 g/cu cm at 22 °CKow (logP) = 3.08 at 25 °CHenry's Law constant = 3X10-6 Pa cu m mol-1 at 20 °Csolubility = 62 mg/L in water at 20 °CDiastereoisomer B: MP = 133.5 °CVP = 4X10-4 mPa at 20 °CSG/Density = 1.299 g/cu cm at 22 °CKow (logP) = 3.28 at 25 °CHenry's Law constant = 4X10-6 Pa cu m mol-1 at 20 °Csolubility = 33 mg/L in water at 20 °C |
| 沸点 | 465.4±55.0 °C(Predicted) |
| 屈折率 | 1.5270 (estimate) |
| 引火点 | 2 °C |
| 貯蔵条件 | 2-8°C |
| pKa（酸解離定数） | 13.29±0.20(Predicted) |
| 外観・状態 | Solid |
| 色 | ホワイトからオフホワイト |
| Merck | 13,9667 |
| BRN | 616470 |
| ヘンリー定数 | 7.6×106 mol/(m3Pa) at 25℃, HSDB (2015) |
| InChI | 1S/C14H18ClN3O2/c1-14(2,3)12(19)13(18-9-16-8-17-18)20-11-6-4-10(15)5-7-11/h4-9,12-13,19H,1-3H3 |
| InChIKey | BAZVSMNPJJMILC-UHFFFAOYSA-N |
| SMILES | CC(C)(C)C(O)C(Oc1ccc(Cl)cc1)n2cncn2 |
| LogP（分配係数） | 2.900 |
| CAS データベース | 55219-65-3(CAS DataBase Reference) |
| NISTの化学物質情報 | Triadimenol(55219-65-3) |
| EPAの化学物質情報 | Triadimenol (55219-65-3) |
安全性と法規制
| GHS 分類 | DangerH302: Harmful if swallowed [Warning Acute toxicity, oral]H360: May damage fertility or the unborn child [Danger Reproductive toxicity]H362: May cause harm to breast-fed children [Reproductive toxicity, effects on or via lactation]H411: Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]P203, P260, P263, P264, P270, P273, P280, P301+P317, P318, P330, P391, P405, and P501 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for 0.9% (1 of 114) of reports. |
|---|---|
| 規制情報 | Hazard Traits - Reproductive ToxicityAuthoritative List - EC Annex VI CMRs - Cat. 1BReport - if used as a fragrance or flavor ingredientCommission Regulation (EC) No 1490/2002Triadimenol is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)2008/125, Reg. (EU) 2022/801, Reg. (EU) No 540/2011Triadimenol: Does not have an individual approval but may be used under an appropriate group standard |
| その他の安全情報 | IMAP assessments - 1H-1,2,4-Triazole-1-ethanol, .beta.-(4-chlorophenoxy)-.alpha.-(1,1-dimethylethyl)-: Human health tier I assessmentIMAP assessments - 1H-1,2,4-Triazole-1-ethanol, .beta.-(4-chlorophenoxy)-.alpha.-(1,1-dimethylethyl)-: Environment tier I assessment |
| 有害性の概要 | Commercial material is mixture of two diastereoisomers[Merck Index] Increased liver enzyme activity (ALT and AST) and histopathological liver changes observed in 13-week feeding study of rats at the three highest doses tested (500, 1,500, and 4,500 ppm)A 15-day dermal study of rabbits produced a NOAEL greater than highest tested dose (250 mg/kg/day)Teratogenic effects seen in tadpoles (branchial arches) and cultured rat embryos (cranial nerve and ganglia)No evidence of mutagenicity[HSDB] Not irritating to skin or eyes of rabbitsNot sensitizing to guinea pig skinNo adverse effects to reproductive performance observed in 2-generation study of ratsNo evidence of primary embryotoxic or teratogenic effects in rats or rabbits administered by gavage in the most sensitive stage of gestation |
用途
説明
Triadimenol is a metabolite of triadimefon , a broad-spectrum chiral triazole fungicide, that is formed by reduction of a carbonyl group to the corresponding alcohol. It is teratogenic, inducing cranial nerve and ganglia abnormalities in a rat post-implantation whole embryo culture model when used at concentrations ranging from 12.5 to 125 μM. In vivo, triadimenol induces embryotoxicity in rats and rabbits when administered orally at doses of 100 and 40 mg/kg, respectively. Embryonic exposure to triadimenol (3-3,000 μg/L) induces embryonic mortality as well as decreases fertility and increases the number of female offspring in medaka fish (O. latipes).
使用
Triadimenol is used for the control of powdery mildews, rusts and Rhynchosporium in cereals, and also as a seed treatment to control bunt, smut and other cereal diseases. It is also used on vines, hops, coffee, tomatoes, vegetables, fruit, tobacco, sugar cane, ornamentals and other crops, mainly against powdery mildews, rusts and various leaf spot diseases.