Flurprimidol 调嘧醇 呋嘧醇 氟嘧醇

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呋嘧醇

调嘧醇,其他名称Cutless,EL-500,性质和作用原药为无色结晶体,注意事项调嘧醇是新型植物生长抑制剂,使用技术尚不成熟,在使用前,要做好用药条件试验后再推广使用。

CAS编码:[56425-91-3
IUPAC名称: (RS)-2-methyl-1-pyrimidin-5-yl-1-(4-trifluoromethoxyphenyl)propan-1-ol
英文通用名称: flurprimidol
中文通用名称: 呋嘧醇
英文商品名称: Cutless; EL-500
中文商品名称: 调嘧醇
英文化学名称: α-(1-methylethyl)-α-[4-(trifluoromethoxy)phenyl]-5-pyrimidinemethanol
中文化学名称:
分子式: C15H15F3N2O2

性质:
白色结晶,熔点94~96℃。在水中的溶解度(pH值4~10)为120~140mg/L,易溶于丙酮、氯仿、二氯甲烷等有机溶剂中。大鼠急性经口LD50709mg/kg,家兔急性经皮LD50>500mg/kg。制剂有50%可湿性粉剂和1%颗粒剂。植物生长调节剂。由对溴苯基三氟甲基醚转化为格氏试剂,并与丁腈反应,产物再与5-溴代嘧啶反应生成。可使植株高度降低,诱发分蘖,增进根生长,提高水稻抗倒伏能力,用量0.45kg/ha。

调嘧醇 - 药品简介
(一)性质和作用原药为无色结晶体,其水溶液遇光分解。大鼠急性经口LD50709毫克/公斤,小鼠急性经口LD50602毫克/公斤,兔急性经皮LD50大于500毫克/公斤,接触皮肤呈轻微的红斑,无内吸毒性,对兔眼睛引起暂时的角膜混虫、中等巩膜炎、轻微的结膜炎。Ames
试验表明调嘧醇无致突变作用。对鸟低毒,对鱼毒性较低,鲤鱼LC50(48小时)13.29毫克/升,蓝鳃太阳鱼LC50(48小时)17.2毫克/升,虹鳟鱼LC50(48小时)18.3毫克/升。50%可湿性粉剂大鼠急性经口LD50大于500毫克/公斤,兔经皮LD50大于2000毫克/公斤,吸入LC50大于2.37毫克/升。调嘧醇属嘧啶醇类植物生长调节剂,是赤霉素合成抑制剂。最大抑制作用在性繁殖阶段,对水稻具生根和抗倒伏作用,在分蘖期施用,主要通过根吸收,然后转移至水稻植株顶部,使植株高度降低,诱发分蘖,增进根的生长。在抽穗前施药提高水稻的抗倒伏能力,不会延迟抽穗或影响水稻产量。可改善冷季和暖季草坪的质量,也可注射树干减缓生长和减少观赏植物的修剪次数,调节株型更具观赏价值。
(二)制剂50%可湿性粉剂。
(三)使用方法
1.草坪可使禾本科草皮、结缕草、狗牙根、黑麦草、剪股颖、早熟禾、鸭茅、梯牧草降低高度,减少修剪次数,每公顷用50%可湿性粉剂1—3公斤(有效成分0.5—1.5公斤),夏末,加水750升喷雾处理(即亩用67—200克,加水50升处理)。早熟禾混合草皮以调嘧醇每公顷有效成分0.84公斤加0.07公斤伏草胺桶混施药可减少早熟禾混合草皮生长,与未处理对照相比,效果达72%。
2.树干涂抹或注射2年火炬松和湿地松喷于叶面或涂于树皮,每公顷用有效成分0.5—2公斤,能减缓生长降低高度。
3.水稻抗倒伏水稻分蘖盛期施用50%可湿性粉剂每公顷1—2公斤(有效成分0.5—1公斤)加水750升,均匀喷雾,可增进根生长,促分蘖,降低植株高度,提高抗倒伏能力。
(四)注意事项调嘧醇是新型植物生长抑制剂,使用技术尚不成熟,在使用前,要做好用药条件试验后再推广使用。

 

 

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flurprimidol
Plant growth regulator
pyrimidinyl carbinol

  Flurprimidol

NOMENCLATURE
Common name flurprimidol (BSI, draft E-ISO, (m) draft F-ISO, ANSI)
IUPAC name (RS)-2-methyl-1-pyrimidin-5-yl-1-(4-trifluoromethoxyphenyl)propan-1-ol
Chemical Abstracts name a-(1-methylethyl)-a-[4-(trifluoromethoxy)phenyl]-5-pyrimidinemethanol
CAS RN [56425-91-3] unstated stereochemistry Development codes EL-500 (Lilly)

PHYSICAL CHEMISTRY
Mol. wt. 312.3 M.f. C15H15F3N2O2 Form Colourless crystals. M.p. 93.5-97 ºC B.p. 264 ºC V.p. 4.85 ´ 10-2 mPa (25 °C) KOW logP = 3.34 (pH 7, 20 ºC) S.g./density 1.34 (24 ºC) Solubility In water 114 (distilled), 104 (pH 5), 114 (pH 7), 102 (pH 9) (all in mg/l, 20 ºC) (OECD 105). In hexane 1.26, toluene 144, dichloromethane 1810, methanol 1990, acetone 1530, ethyl acetate 1200 (all in g/l). Stability After 5 d at pH 4, 7 and 9 (50 ºC), <10% hydrolysis had occurred. Stable for at least 14 mo at room temperature. Photolytically decomposed in water, DT50 c. 3 h.

COMMERCIALISATION
History Plant growth regulator reported by G. E. Brown et al. (Abstr. Weed Sci. Soc. Am., No. 84, 1981). Introduced in USA (1989) by Eli Lilly & Co. (agrochemical interests now Dow AgroSciences). Rights acquired by SePRO Corp. in 2001. Patents US 4002628 Manufacturers SePRO

APPLICATIONS
Biochemistry Gibberellin synthesis inhibitor. Mode of action Plant growth regulator, absorbed by the leaves and roots, with translocation in the xylem and phloem. Reduces internode elongation. Uses Used to decrease the rate of growth in a wide range of mono- and dicotyledonous species, including perennial turf grasses, ornamental cover species, herbaceous and woody ornamentals, and deciduous and coniferous trees. Application rate for turf grasses is 0.125-1 lb/a; foliar rates for bedding plants are 2-80 ppm, for flowering and foliage plants 5-30 ppm, for woody ornamentals 100-200 ppm. Formulation types EC; SC; WP. Selected products: 'Cutless' (Sepro)

OTHER PRODUCTS
'Greenfield' (Sepro); 'Topflor' (Sepro)

ANALYSIS
Product analysis by glc with FID, or by hplc with u.v. detection. Residues in water or soils determined by glc with ECD, or by gc-ms (S. D. West in Comp. Anal. Profiles, Chapt. 9; S. D. West & B. S. Rutherford, J. Assoc. Off. Anal. Chem., 1986, 69, 572).

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for male rats 914, female rats 709, male mice 602, female mice 702 mg/kg. Skin and eye Acute percutaneous LD50 for rabbits >5000 mg/kg. Slight to moderate irritant to skin and eyes (rabbits). Not a skin sensitiser (guinea pigs). Inhalation LC50 (4 h) for rats >5 mg/l. NOEL (1 y) for dogs 7 mg/kg b.w. daily; (2 y) for rats 4, mice 1.4 mg/kg b.w. daily. ADI Not used on food crops. Other No teratogenic effects observed at doses of 200 mg/kg daily (rats) or 45 mg/kg daily (rabbits). Negative in Ames, DNA repair, primary rat hepatocyte and other in vitro assays. Toxicity class WHO (a.i.) III

ECOTOXICOLOGY
Birds Acute oral LD50 for quail and mallard ducks >2000 mg/kg. Dietary LC50 (5 d) for quail 560, mallard ducks 1800 mg/kg diet. Fish LC50 (96 h) for bluegill sunfish 17.2, rainbow trout 18.3 ppm. Daphnia LC50 (48 h) 11.8 ppm. Algae EC50 for Selenastrum capricornutum 0.84 mg/l. Bees LD50 (contact, 48 h) >100 mg/bee.

ENVIRONMENTAL FATE
Animals In mammals, the skin forms a significant barrier to absorption. Following oral administration, excretion follows in the urine and faeces within 48 hours, and more than 30 metabolites have been identified. No accumulation potential. Soil/Environment Degradation in soil under aerobic conditions leads to more than 30 metabolites. Soil Kd 1.7 on sandy loam.