Cycloxydim 噻草酮

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噻草酮

CAS登录号:99434-58-9
英文名称:cycloxydim
化学名称:(±)2-(1-(乙氧亚氨基)丁基)-3-羟基-5-噻烷-3-基环己-2-烯酮 ;(±)-2-(1-(ethoxyimino)butyl)-3-hydroxy-5-thian-3-ylcyclohex-2-enone
其他名称:草噻喃;Stratos;Focus;Laser;
分子式:C7H17NO3S
分子量:325.5

理化性质:纯品黄色固体(熔点以上深褐色). 密度:1.12(20℃),熔点:37~39℃ ,蒸气压:0.01mPa(20℃) ,溶解度(20℃);水85mg/kg,易溶于大多数有机溶剂。稳定性;30℃以上不稳定。

毒性LD50(mg/kg):大鼠急性经口LD50为3940。急性经皮LD50大于2000。原药对蜜蜂无诱变性。饲喂试验的无作用剂量:大鼠18个月100mg/kg饲料(7mg/(kg·d)),小鼠2a240mg/kg饲料(32mg/(kg·))。

作用特点及杀草谱:本品属烷基环己烯基酮类除草剂。是有丝分裂抑制剂。为选择性芽后除草剂,用于防除阔叶作物棉花、亚麻、油菜、马铃薯、大豆、甜莱、向日葵和蔬菜田中,防除一年生和多年生禾本科杂草,如野燕麦、鼠尾看麦娘、黑麦草、自生禾谷类、大剪股颖。以100~250g(a.i.)/ha剂量施用,可有效防除一年生禾本科杂草。施用时,外加 1~2L油/ha可增加防除效果。本品在土壤中,持效期2周内减少10%(20~22℃)。

剂型:20%乳油

生产方法:5-(噻烷-3-基)-环己-1,3-二酮与丁酰氯丁酰化后。再与乙氧基胺盐酸盐在乙醇中反应即得。

生产情况:巴斯夫公司1987年开发的除草剂。天津一方科技有限公司生产。

其他:专利到期

 

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cycloxydim
Herbicide
HRAC A WSSA 1; cyclohexanedione oxime

  Cycloxydim

NOMENCLATURE
Common name cycloxydim (BSI, draft E-ISO); cycloxydime ((f) draft F-ISO)
IUPAC name (?-2-[1-(ethoxyimino)butyl]-3-hydroxy-5-thian-3-ylcyclohex-2-enone
Chemical Abstracts name 2-[1-(ethoxyimino)butyl]-3-hydroxy-5-(tetrahydro-2H-thiopyran-3-yl)-2-cyclohexene-1-one; in an early publication, the tautomer 2-[1-(ethoxyamino)butylidene]-5-(tetrahydro-2H-thiopyran-3-yl)-1,3-cyclohexanedione was named
CAS RN [101205-02-1] cycloxydim; [99434-58-9] for tautomer Development codes BAS 517H (BASF)

PHYSICAL CHEMISTRY
Mol. wt. 325.5 M.f. C17H27NO3S Form Colourless, odourless crystals; (tech., yellow beige crystals, with a weak aromatic odour; dark brown oil above m.p.). M.p. c. 41 ºC V.p. 0.01 mPa (20 ºC) KOW logP = c. 1.36 (pH 7, 25 ºC). Henry 6.1 ´ 10-5 Pa m3 mol-1 (calc.) S.g./density 1.165 (20 ºC) Solubility In water 53 mg/l (pH 4.3, 20 ºC). In acetone, ethanol, dichloromethane, ethyl acetate, toluene >250 (all in g/l, 20 ºC). In n-hexane 29 g/kg (20 ºC). Stability Stable at room temperature for ³1 y; unstable above 30 ºC; decomposes c. 200 ºC. DT50 in argon atmosphere at 20 000 lux (simulated sunlight, 15-20 ºC) >192 h; in air at 80 000 lux (simulated sunlight, 20 ºC) 0.8 h. pKa c. 4.17 F.p. 89.5 ºC (tech.)

COMMERCIALISATION
History Herbicide reported by W. Zwick et al. (Proc. Br. Crop Prot. Conf. - Weeds, 1985, 1, 85) and by N. Meyer et al. (ibid., p. 93). Introduced by BASF AG; first marketed in France 1989. Patents EP 70370; EP 71707; US 4422864; DE 3121355 Manufacturers BASF

APPLICATIONS
Biochemistry Fatty acid synthesis inhibitor, by inhibition of acetyl CoA carboxylase (ACCase). Mitosis inhibitor. Mode of action Selective herbicide, absorbed rapidly by the foliage, with translocation both acropetally and basipetally. Uses Post-emergence control of annual and perennial grasses (except red fescue and Poa spp.) in broad-leaved crops (e.g. oilseed rape, beans, potatoes, brassicas, cotton, celery, fennel, beetroot, sugar beet, fodder beet, sunflowers, soya beans, flax, alfalfa, crucifers, alliums). Applied at 100-400 g/ha against annual grasses, 500-600 g/ha against Agropyron repens. Phytotoxicity Non-phytotoxic to all broad-leaved crops, when used as directed. Phytotoxic to graminaceous crops. Formulation types EC. Compatibility Should not be mixed with broad-leaved herbicides. Selected products: 'Focus' (BASF); 'Laser' (BASF); 'Stratos' (BASF)

OTHER PRODUCTS
'Valentia' (GreenCrop)

ANALYSIS
Product analysis by hplc. Residues analysed by derivatisation to glutaric acid derivatives and measurement by glc with S-FPD. Details available from BASF.

MAMMALIAN TOXICOLOGY
Reviews FAO/WHO 65, 67 (see part 2 of the Bibliography). Oral Acute oral LD50 for rats c. 5000 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. Non-irritating to skin and eyes (rabbits). Inhalation LC50 (4 h) for rats >5.28 mg/l. NOEL (18 mo) for rats 7 mg/kg b.w. daily; (2 y) for mice 32 mg/kg b.w. daily. ADI (JMPR) 0.07 mg/kg [1992]. Other Non-mutagenic, non-carcinogenic, non-teratogenic. Toxicity class WHO (a.i.) U; EPA (formulation) IV

ECOTOXICOLOGY
Birds Acute oral LD50 for quail >2000 mg/kg. Fish LC50 (96 h) for trout 220, bluegill sunfish >100 mg/l. Daphnia LC50 (48 h) 132 mg/l. Algae EC50 for Pseudokirchneriella subcapitata >100 mg/l. Other aquatic spp. EC50 for Lemna gibba >100 mg/l. Bees Non-toxic to bees; LD50 >100 mg/bee. Worms LC50 for Eisenia foetida >1000 mg/kg soil.

ENVIRONMENTAL FATE
Animals See Soil/Environment. Plants See Soil/Environment. Soil/Environment Rapidly broken down in plants, animals and in the soil by oxidation, conjugation, rearrangement, hydroxylation, and reductive ether-cleavage (Proc. Br. Crop Prot. Conf. - Pests Dis., 1988, 1, 335-341). DT50 (lab.) 0.5-12 d (20 ºC). Koc <10-183.