Tridemorph 十三吗啉

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十三吗啉;
CAS号: 24602-86-6
英文名称: Tridemorph
化学名称:2,6-二甲基十三烷基吗啉; 2,6-dimethyl-4-tridecyl-morpholin
其他名称:三得芬; 克啉菌;异十三吗啉;卡拉西内酯,克力星;
分子式: C19H39NO
分子量: 297.52

理化性质:纯品为无色油状液体,略有氨味。b.p.134℃/66.65Pa、 130~131℃/22.7Pa,蒸气压 1.27×10-2Pa (20℃)。能溶于丙酮、氯仿、苯、乙醇等有机溶剂,常温下在水中溶解度为0.01%。常温下贮存稳定。

毒性:中毒。口服- 大鼠 LD50: 650 毫克/公斤; 口服- 小鼠 LD50: 1560 毫克/ 公斤。无致突变和致癌现象发生。

作用特点及用途:吗啉类杀菌剂,兼有保护、治疗和内吸作用,残效长,对作物无药害,抑菌谱比较广,对担子菌、子囊菌和半知菌引起的多种植物病害有效,其作物机制为抑制麦角甾醇的生物合成。用于防治大麦、小麦的白粉病,小麦叶锈病、条锈病,黄瓜、马铃薯、橡胶、豌豆的白粉病。以及茶叶茶饼病等病害的防治,也用于橡胶树红根病的防治。

剂型:60%、 75%十三吗啉乳油,86% OL,10%膏剂。混剂如十三吗啉+多菌灵+代森锰、十三吗啉+丙环唑等。

生产方法:由[CH3CH(OH)CH2]2NC13H27在200℃、辛醇和三氧化二铝存在下,脱水、关环反应制得。

生产情况:上虞奥复托化工有限公司;江苏飞翔化工股份有限公司;南通维立科化工有限公司(600t/a);青岛博尔生物化学有限公司;绍兴市巨富化工有限公司;浙江世佳科技有限公司;陕西美邦农药有限公司;辽宁省化工研究院

价格:十三吗啉原药价格12万元/吨

 

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tridemorph
Fungicide
FRAC 5, G2; morpholine: morpholine

  tridemorph

NOMENCLATURE
Common name tridemorph (BSI, E-ISO); tridémorphe ((m) F-ISO) for a reaction mixture (see below)
IUPAC name 4-alkyl-2,6-dimethylmorpholine; for original definition, 2,6-dimethyl-4-tridecylmorpholine
Chemical Abstracts name for original structure/main component, 2,6-dimethyl-4-tridecylmorpholine
CAS RN [81412-43-3] new definition; [24602-86-6] 4-tridecyl- component EEC no. 246-347-3 (for 4-tridecyl- component) Development codes BASF 220 F

PHYSICAL CHEMISTRY
Composition Originally thought to consist only of tridecyl (C13) isomers, the reaction mixture has now been shown to comprise C11 to C14 homologues containing 60-70% of 4-tridecyl isomers, 0.2% C9 and C15 homologues and 5% of 2,5-dimethyl isomers. Mol. wt. 297.5 (approx.) M.f. C19H39NO (approx.) Form Yellow, oily liquid, with a slight amine-like odour. B.p. 134 ºC/0.4 mmHg (tech.) V.p. 12 mPa (20 °C) KOW logP = 4.20 (pH 7, 22 °C) Henry 3.2 Pa m3 mol-1 (calc.) S.g./density 0.86 (tech.) (20 °C) Solubility In water 1.1 mg/l (pH 7, 20 ºC). Miscible with ethanol, acetone, ethyl acetate, cyclohexane, diethyl ether, benzene, chloroform, olive oil. Stability Stable £50 ºC. On u.v. irradiation of an aqueous solution containing 20 mg/kg, 50% hydrolysis occurs in 16.5 h. pKa 6.50 (20 ºC), base F.p. 142 °C (Pensky-Martens)

COMMERCIALISATION
History Fungicide reported by J. Kradel et al. (Proc. Br. Insectic. Fungic. Conf., 5th, 1969, 1, 16) and by E. H. Pommer et al. (ibid., 1969, 2, 347). Introduced in Germany (1969) by BASF AG. Patents DE 1164152 Manufacturers BASF

APPLICATIONS
Biochemistry Ergosterol biosynthesis inhibitor, by inhibition of steroid reduction (sterol-D14-reductase) and isomerisation (D8 to D7-isomerase). Mode of action Systemic fungicide with eradicant action. Absorbed by the leaves and roots, giving some protective action. Uses Control of Erysiphe graminis in cereals, Mycosphaerella spp. in bananas, Corticium salmonicolor and Exobasidium vexans in tea, and Oidium heveae in hevea. Mixed with carbendazim to extend spectrum of cereal diseases controlled. Phytotoxicity Scorch may occur on some winter wheat varieties under certain climatic conditions. Formulation types OL. Selected products: 'Calixin 86' (bananas) (BASF)

OTHER PRODUCTS
'Calixin' (BASF) mixtures: 'Opus Forte' (+ epoxiconazole) (BASF); 'Opus Plus' (+ epoxiconazole) (BASF); 'Rockett Ultra' (+ fenpropimorph) (BASF); 'Tango Duo' (+ epoxiconazole) (BASF); 'Granit TR' (+ bromuconazole) (Bayer CropScience) Discontinued products mixtures: 'BAS 46402F' * (+ fenpropimorph) (BASF); 'Cosmic' * (+ carbendazim+ maneb) (BASF); 'Gemini' * (+ fenpropimorph) (BASF); 'Meld' * (+ flusilazole) (BASF); 'Allicur' * (+ tebuconazole) (spray, UK) (Bayer); 'Alto Major' * (+ cyproconazole) (Novartis, Sandoz); 'Aurore' * (+ tebuconazole) (spray, France) (Bayer); 'Cerelux' * (+ flusilazole) (DuPont); 'Colt' * (+ triadimenol) (Bayer); 'Dipper' * (+ tebuconazole) (Bayer); 'Dorin' * (+ triadimenol) (Bayer); 'DUK 51' * (+ fenpropimorph+ flusilazole) (DuPont); 'Fusion' * (+ flusilazole) (DuPont); 'Gral' * (+ flusilazole) (DuPont); 'Joust' * (+ propiconazole) (Unicrop); 'Justice' * (+ fenpropimorph+ flusilazole) (DuPont); 'Moot' * (+ cyproconazole) (Novartis); 'Option' * (+ flusilazole) (DuPont); 'Tilt Turbo' * (+ propiconazole) (Ciba); 'Unison' * (+ fenbuconazole) (PBI)

ANALYSIS
Product analysis by acid-base titration. Residues in cereal straw and soil determined by colorimetry of a derivative or by gc-ms. Details available from BASF.

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for rats 480 mg/kg. Skin and eye Acute percutaneous LD50 for rats >4000 mg/kg. Skin irritant; not an eye irritant (rabbits). Inhalation LC50 (4 h) for rats 4.5 mg/l air. NOEL (2 y) for rats 30 mg/kg diet (c. 1.8 mg/kg daily), for dogs 50 ppm diet. ADI 0.016 mg/kg b.w. Toxicity class WHO (a.i.) II; EPA (formulation) III EC classification R61| Xn; R20/22| Xi; R38| N; R50, R53 (for 4-tridecyl- component)

ECOTOXICOLOGY
Birds LD50 for quail 1388, ducks >2000 mg/kg. Fish LC50 (96 h) for trout 3.4 mg/l. Daphnia LC50 (48 h) 1.3 mg/l. Algae EC50 (96 h) 0.28 mg/l. Bees LD50 (24 h) >200 mg/bee. Worms LC50 (14 d) for Eisenia foetida 880 mg/kg.

ENVIRONMENTAL FATE
Animals In rats, following oral administration, tridemorph is rapidly absorbed, and is almost completely eliminated within 2 days. Plants Residues in cereal grains at harvest are <0.05 mg/kg, mostly polar material. Metabolism proceeds via oxidation of the 4-alkyl side-chain and/or by opening of the morpholine ring. Soil/Environment DT50 (lab.) 20-50 d, (field) 14-34 d. Koc 2500-10 000.