Dodemorph 十二环吗啉

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十二环吗啉

CAS号:1593-77-7
英文名称:Dodemorph
化学名称:N-环十二烷基-2,6-二甲基吗啉;4-cyclododecyl-2,6-dimethylmorpholine
其他名称:吗菌灵
分子式:C18H35NO
分子量:281.48

理化性质:原药顺反异构体比例为60%:40%,黄色液体,相对密度约0.93。水中溶解度<100 mg/kg.,氯仿中>1000,乙醇中50,丙酮中57,乙酸乙酯中185(g/l, 20 ℃),不溶于碱性溶剂。在密闭容器中存放可稳定一年以上,其分解产物易燃。
毒性:40%液剂对大鼠急性经口LD504.5mg/kg。
作用特点及用途:麦角甾醇生物合成抑制剂, 内吸性杀菌剂,对植物有治疗和保护作用。可防治黄瓜及其他作物的白粉病等。
剂型:40%液剂
生产方法:由相应二醇闭环制得。
生产情况:江苏飞翔化工股份有限公司

 

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dodemorph
Fungicide
FRAC 5, G2; morpholine: morpholine

  dodemorph

NOMENCLATURE
dodemorph
Common name dodemorph (BSI, E-ISO); dodémorphe ((m) F-ISO)
IUPAC name 4-cyclododecyl-2,6-dimethylmorpholine
Chemical Abstracts name 4-cyclododecyl-2,6-dimethylmorpholine
CAS RN [1593-77-7]; dodemorph was originally reported in the literature with an incorrect structure [35842-17-2] EEC no. 216-474-9

dodemorph acetate
Common name dodemorph acetate (BSI, E-ISO); acétate de dodémorphe (F-ISO)
IUPAC name 4-cyclododecyl-2,6-dimethylmorpholinium acetate
CAS RN [31717-87-0] Development codes BAS 238F (BASF)

PHYSICAL CHEMISTRY
dodemorph
Composition Dodemorph contains cis- (c. 60% m/m) and trans- (c. 40%) isomers. Mol. wt. 281.5 M.f. C18H35NO Form The trans- isomer is a colourless oil. The cis- isomer is a colourless solid, with characteristic odour. M.p. 71 ºC B.p. c. 190 ºC/1 mmHg V.p. cis- isomer: 0.48 mPa (20 ºC) KOW logP = 4.14 (pH 7) Solubility cis- isomer: In water <100 mg/kg. In chloroform >1000, ethanol 50, acetone 57, ethyl acetate 185 (all in g/l, 20 ºC). Stability Stable to heat, light and water. pKa 8.08

dodemorph acetate
Composition Dodemorph acetate contains cis- (c. 50-60% m/m) and trans- (c. 50-40%) isomers; tech. has a nominal content of 96% a.i. Mol. wt. 341.5 M.f. C20H39NO3 Form Colourless solid; (tech., viscous yellow liquid). M.p. 63-64 ºC; cis- isomer 72 ºC B.p. 315 °C/101.3 kPa V.p. 12 mPa (25 ºC, gas saturation method) KOW logP = 2.52 (pH 5), 4.23 (pH 9) Henry 0.008 Pa m3 mol-1 (calc.) S.g./density c. 0.93 Solubility In water 736 (pH 5), 520 (pH 7), 2.29 (pH 9) (all in mg/l, 25 ºC). In benzene, chloroform >1000, cyclohexane 846, ethyl acetate 205, ethanol 66, acetone 22 (all in g/kg, 20 ºC). Stability Stable in unopened containers for >1 y. Stable at 50 ºC for ³2 y. Stable in neutral, moderate alkaline or acidic media. F.p. Forms flammable decomposition products at high temperature

COMMERCIALISATION
History Fungicidal properties of morpholines with large groups attached to the nitrogen described by K. H. König et al. (Angew. Chem., 1965, 77, 327); those of dodemorph by J. Kradel & E. H. Pommer (Proc. Br. Insectic. Fungic. Conf., 4th, 1967, 1, 170). Dodemorph acetate introduced in Germany (1968) by BASF AG. Patents DE 1198125 Manufacturers BASF

APPLICATIONS
dodemorph acetate
Biochemistry Steroid reduction (ergosterol biosynthesis) inhibitor. Mode of action Dodemorph acetate is a systemic fungicide with protective and curative action. Absorbed through the leaves and roots, with translocation. Uses Control of powdery mildews on roses and other ornamentals (outdoors and under glass). Applied at 100 g/100 l (1-2 kg/ha). Phytotoxicity Cinerarias, begonias, and some varieties of rose may be injured. Formulation types EC. Selected products: 'Meltatox' (BASF)

OTHER PRODUCTS
dodemorph acetate
'F238' (BASF); 'Mehltaumittel' (BASF) Discontinued products: 'Milban' * (Grace-Sierra)

ANALYSIS
Product analysis by potentiometric titration with perchloric acid in glacial acetic acid. Residues in crops analysed by glc.

MAMMALIAN TOXICOLOGY
dodemorph
Toxicity class WHO (a.i.) U EC classification Xi; R36/37/38| N; R51, R53

dodemorph acetate
Oral Acute oral LD50 for male rats 3944, female rats 2465 mg/kg. Skin and eye Acute percutaneous LD50 for rats >4000 mg/kg (for 42.6% EC formulation). Skin irritant and severe eye irritant (rabbits). Inhalation LC50 (4 h) for rats 5 mg/l air (for EC formulation). EC classification (Xi; R34, R41| R43| R51, R53)

ECOTOXICOLOGY
dodemorph acetate
Fish LC50 (96 h) for rainbow trout 2.2, guppies c. 40 mg/l. Daphnia LC50 (48 h) 1.8 mg/l. Algae ErC50 (72 h) for Selenastrum capricornutum 1.1 mg/l. Bees Non-toxic to bees; LD50 (oral) >138.8 µg/bee; (contact) >100 µg/bee. Worms LC50 14 d >1000 mg/kg.

ENVIRONMENTAL FATE
Soil/Environment In soil, after 100 d, 23% non-extractable residues, 18% mineralisation and no relevant metabolites were found; DT50 26-73 d. High adsorption, no risk of leaching;Koc 4200-48 000.