Oxadixyl 恶霜灵

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恶霜灵

CAS号: 77732-09-3
英文名称:oxadixyl
化学名称: 2-甲氧基-n-(2-氧代-1,3-噁唑烷-3-′基)乙酰胺-n-(2′,6′-二甲基苯)
其他名称:杀毒矾,噁酰胺;噁唑烷酮,sandofan;metoxazon;metidaxyl;san-371-f;m-10797
分子式:C14H18N2O4
分子量:278.4

理化性质:无色晶体。熔点104~105℃,蒸气压3.3Mpa(20℃),溶解性(25℃):水3.4克/公斤,乙醇50克/公斤,甲醇112克/公斤。二甲基亚砜39.0%,丙酮34.4%,二甲苯1.7%。其水溶液在ph值5~9(<70℃)情况下稳定。

毒性ld50(mg/kg):大白鼠急性经口3380(雄)、1860(雌),小白鼠急性经口1860(雄)、2150(雌),雄大白鼠急性经皮大于2000。对兔眼睛和皮肤物刺激作用,对豚鼠皮肤无过敏性。

作用特点及用途:农用杀菌剂。对霜霉目病源菌具有很高的防效,有保护和治疗作用,持效期长。用于防治霜霉目病原菌如烟草、黄瓜、葡萄、蔬莱的霜霉病、疫病等,并能兼治多种继发性病害如褐斑病、黑腐病等。具体病害如烟草黑胫病、番茄晚疫病、黄瓜霜霉病、茄子绵疫病、辣椒疫病、马铃薯晚疫病、白菜霜霉病、葡萄霜霉病。

田间试验表明,以250mg/l使用,持效期9~10天,对病害的治疗作用达3天以上;以500mg/l防治葡萄霜霉病,持效期16天以上,8mg/l为2天,30~120mg/l为7~11天。与代森锰锌混合,其防效高于与灭菌丹、铜制剂混用,

剂型:制剂FG、WG、WP。单剂如:25%可湿性粉剂。混剂如:本品+敌菌丹+氯氟氰菊酯,本品+苯氟磺胺,本品士丙森锌,本品+敌菌丹,本品+灭菌丹,本品+霜脲氰+代森锰锌,本品+霜脲氰+氢氯化铜,本品+氧氯化铜+硫酸铜十灭菌丹,本品+氧氯化铜+硫酸铜+代森锰锌,本品+亚乙基双基双(二硫代氨基甲酸)锌氨合物(聚亚乙基秋兰姆二硫化物)等,如64%恶霜·锰锌可湿性粉剂(杀毒矾)。

生产方法:2,6-二甲基苯胺经重氮化、还原制得2,6-二甲基苯肼。由2,6-二甲基苯肼与氯代甲酸溴丙酯在吡啶-苯溶剂中,进行环化缩合反应,得3-(2,6-二甲基苯胺基)噁唑烷-2-酮,最后与甲氧基乙酰氯反应制得。

生产情况:江苏省江阴农药厂;西安近代农药科技股份公司,日月化工有限公司
 

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oxadixyl
Fungicide
FRAC 4, A1; phenylamide: oxazolidinone

  oxadixyl

NOMENCLATURE
Common name oxadixyl (BSI, draft E-ISO, draft F-ISO)
IUPAC name 2-methoxy-N-(2-oxo-1,3-oxazolidin-3-yl)aceto-2',6'-xylidide
Chemical Abstracts name N-(2,6-dimethylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl)acetamide
CAS RN [77732-09-3] Development codes SAN 371F (Sandoz)

PHYSICAL CHEMISTRY
Mol. wt. 278.3 M.f. C14H18N2O4 Form Colourless, odourless crystals. M.p. 104-105 ºC V.p. 0.0033 mPa (20 ºC) KOW logP = 0.65-0.8 (22-24 ºC) Henry 2.70 ´ 10-7 Pa m3 mol-1 (calc.) S.g./density Bulk density 0.5 kg/l Solubility In water 3.4 g/kg (25 ºC). In acetone 344, dimethyl sulfoxide 390, methanol 112, ethanol 50, xylene 17, diethyl ether 6 (all in g/kg, 25 ºC). Stability Stable under normal conditions, and when stored at 70 ºC for 2-4 weeks. A 20 ppm solution of the a.i. is stable in aqueous buffer solutions of pH 5, 7 and 9 at room temperature, DT50 c. 4 y.

COMMERCIALISATION
History Systemic fungicide reported by U. Gisi et al. (Meded. Fac. Landbouwwet. Rijksuniv. Gent, 1983, 48, 541). Introduced by Sandoz AG (now Syngenta AG) and first marketed in 1984. Patents GB 2058059 Manufacturers Syngenta

APPLICATIONS
Biochemistry It is assumed that it inhibits protein synthesis in fungi, by interference with the synthesis of ribosomal RNA. Mode of action Systemic fungicide with curative and protective action. Rapidly absorbed by the leaves and roots, with translocation principally acropetally, but also basipetally and by translaminar movement. Exhibits a synergistic effect with contact fungicides. Uses In combination with contact fungicides, for control of Peronosporales, such as downy mildews, late blights, and rusts, in vines, maize, potatoes, tobacco, hops, sunflowers, citrus, fruit and vegetables, and as a seed dressing on cotton, peas and sunflowers. Application rates for foliar use, 200-300 g/ha. Formulation types FG; WG; WP. Selected products: 'Anchor' (Gustafson); mixtures: 'Pulsan' (+ cymoxanil+ mancozeb) (Syngenta); 'Sandofan' (+ mancozeb) (Syngenta)

OTHER PRODUCTS
'Blason' (Syngenta) mixtures: 'Apron Elite' (+ thiram+ carbendazim+ cymoxanil) (Syngenta); 'Recoil' (+ mancozeb) (Syngenta); 'Ripost' (+ cymoxanil+ mancozeb) (Syngenta); 'Wakil' (+ thiram+ carbendazim+ cymoxanil) (Syngenta); 'Sirdate P' (+ cymoxanil+ maneb) (Griffin); 'Sirdate S' (+ cymoxanil+ folpet) (DuPont); 'Trustan' (+ cymoxanil+ mancozeb) (DuPont)

ANALYSIS
By rp hplc with u.v. detection (CIPAC Handbook, 1995, G, 122-127) or by glc with TSD; details available from Syngenta.

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for male rats 3480, female rats 1860 mg/kg. Skin and eye Acute percutaneous LD50 for rats and rabbits >2000 mg/kg. Non-irritating to skin and eyes (rabbits), nor a skin sensitiser to guinea pigs. Inhalation LC50 (6 h) for male and female rats >5.6 mg/l air. NOEL (1 y) for dogs 500 mg/kg diet; (90 d and lifetime) for rats 250 mg/kg diet. Not teratogenic in rabbits (up to 200 mg/kg b.w. daily) or rats (up to 1000 mg/kg b.w. daily) and no significant effect on reproduction in rats (up to 1000 mg/kg diet). Other Acute i.p. LD50 for male rats 490, female rats 550 mg/kg. Not mutagenic in the Ames, micronucleus and other standard assays. Toxicity class WHO (a.i.) III; EPA (formulation) III EC classification (Xn; R22)

ECOTOXICOLOGY
Birds Acute oral LD50 for mallard ducks >2510 mg/kg. Dietary LC50 (8 d) for mallard ducks and Japanese quail >5620 mg/kg. Fish LC50 (96 h) for carp >300, rainbow trout >320, bluegill sunfish 360 mg/l. Does not bioaccumulate in fish. Daphnia LC50 (48 h) 530 mg/l. Algae IC50 for Scenedesmus subspicatus 46 mg/l. Bees LD50 (oral) >200 mg/bee; (contact) >100 mg/bee. Worms LD50 (14 d) for earthworms >1000 ppm (mg a.i./kg dry soil).

ENVIRONMENTAL FATE
Animals In rats, following oral administration, absorption is rapid and almost complete, with 81-92% eliminated within 144 hours, in the urine and faeces. Extensive metabolism occurs, mainly by hydrolysis at various points on the methoxyacetamide moiety, and oxidation of the methyl group on the phenyl ring to the corresponding alcohol. Similar metabolites are found in soil and in plants. Plants In plants, the major part (>94%) of the applied dosage remains unchanged. A maximum of 9% penetrates the leaf surface after 42 days, and c. 42% of this is metabolised. Soil/Environment In laboratory experiments, DT50 was 6-9 mo. However, in the field, DT50 values of 2-3 mo were observed. In soil, the main metabolite is oxadixyl acid.