Propaquizafop 喔草酯

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喔草酯

CAS号: 111479-05-1
英文名称: propaquizafop
化学名称:2-异亚丙基氨基氧乙基(R)-2-(4-(6-氯喹喔啉-2-基氧)苯氧基)丙酸酯; (4-((6-chloro-2-quinoxalinyl)oxy)phenoxy)-propanoicaci2-(((1-methylethy;
其他名称:恶草酸
分子式:C22H22ClN3O5
分子量:443.88

理化性质 :纯品为无色晶体,熔点66.3℃,相对密度1.30,蒸气压4.4×10-7mPa(25℃)、1.3×10-7mPa(20℃)。分配系数KowlogP=4.78(25℃)。Henry常数9.2×10-8Pa m3 mol-1。水中溶解度(25℃)0.63mg/L;其他溶剂中溶解度(g/L.25℃):丙酮730,乙醇59,甲苯630,正乙烷37。稳定性:室温下,密闭容器中稳定≥2a,25℃、pH5和pH7时对水解稳定,对光稳定。

毒 性 :大鼠急性经口LD50>5000mg/kg,小鼠急性经口LD503009mg/kg。大鼠急性经皮LD50>2000mg/kg,大鼠急性吸入LC50(4h)2.5mg/L空气。对兔皮肤无刺激性,对兔眼有轻微刺激性,无诱变性,无致畸和胚胎毒性。大、小鼠2年喂养试验无作用剂量为1.5mg/kg.d,狗1年喂养试验无作用剂量为20mg/kg.d。ADI值0.015mg/kg。饲喂LC50野鸭(10d)与山齿鹑(14d)>6593mg/kg.鱼毒LC50(96h,mg/L):虹鳟1.2、鲤鱼0.19、大翻车鱼0.34。蜜蜂LD50(48h)>20μg/只(经口),>200μg/只(接触)。蚯蚓LD50(14d)>1000mg/kg土壤。

作用特点及杀草谱:乙酰辅酶A羧化酶(ACCase)抑制剂,一种苗后选择性苯氧羧酸类除草剂,茎叶处理后能很快被禾本科杂草的叶子吸收导整个植株,积累于植物分生组织,抑制植物体内乙酰辅酶A羧化酶,导致脂肪酸合成受阻而杀死杂草。可迅速被植株的叶和根吸收,并转移至整个植株。苗后施药4d后,敏感的禾本科杂草停止生长,施药后7~12d,植株组织发黄或着红色,在经3~7d后枯死。从施药到杂草死亡一般需10~20d。适宜作物包括大豆、棉花、油菜、甜菜、马铃薯、花生和蔬菜等,主要用于防除众多的一年生和多年生禾本科杂草如阿拉伯高粱、匍匐冰草、狗牙根等。即使在较底温度时也有效。

剂型:10%乳油

生产方法:邻硝基-对氯苯胺用氯代乙酰氯酰化后,在钯催化下加氢还原,还原产物经环合、氯化,制得2,6-二氯代喹喔啉,然后与对苯二酚反应,生成物与相应的对甲苯磺酸酯反应,即制得产品。

生产情况:汽巴-嘉基公司开发的广谱内吸除草剂。国内生产企业:南通嘉禾化工有限公司;无锡禾美农化科技有限公司

 

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propaquizafop
Herbicide
HRAC A WSSA 1; aryloxyphenoxypropionate

  propaquizafop

NOMENCLATURE
Common name propaquizafop (BSI, draft E-ISO, (m) draft F-ISO)
IUPAC name 2-isopropylideneamino-oxyethyl (R)-2-[4-(6-chloroquinoxalin-2-yloxy)phenoxy]propionate
Chemical Abstracts name (R)-2-[[(1-methylethylidene)amino]oxy]ethyl 2-[4-[(6-chloro-2-quinoxalinyl)oxy]phenoxy]propanoate
CAS RN [111479-05-1] Development codes Ro 17-3664/000 (Dr Maag); CGA 233 380 (Ciba)

PHYSICAL CHEMISTRY
Composition (R)- isomer. Mol. wt. 443.9 M.f. C22H22ClN3O5 Form Off-white powder; tech. is an orange to brown mixture of fine powder and granular material. M.p. 66.3 °C B.p. decomp. 260 °C V.p. 4.4 ´ 10-7 mPa (25 ºC, OECD 104; EEC A.4) KOW logP = 4.78 (25 ºC) Henry 9.2 ´ 10-8 Pa m3 mol-1 (20 °C, calc.) S.g./density 1.30 (20 ºC) Solubility In water 0.63 g/m3 (20 ºC, pH 6.8).In acetone, dichloromethane, ethyl acetate and toluene >500, n-hexane 11, methanol 76, n-octanol 30 (all in g/l, 25 ºC). Stability Stable ³2 y in closed container at room temperature. Hydrolytic DT50 10.5 d (pH 5), 32.0 d (pH 7), 12.9 h (pH 9) (all at 25 °C). Stable to u.v. light. pKa -2.3 (est.)

COMMERCIALISATION
History Herbicide reported by P. F. Bocion et al. (Proc. 1987 Br. Crop Prot. Conf. - Weeds, 1, 55). Introduced by Dr R. Maag Ltd. (became Novartis Crop Protection AG). Sold to Makhteshim-Agan Industries in 2000. Patents EP 52798, US 4545807 Manufacturers Makhteshim-Agan

APPLICATIONS
Biochemistry Fatty acid synthesis inhibitor, by inhibition of acetyl CoA carboxylase (ACCase). Mode of action Systemic post-emergence herbicide. Absorbed by foliage and roots and translocated throughout the plant. Treated grasses cease growth within 3-4 days, show chlorosis of younger plant tissues, followed by a progressive collapse of the entire plant 10-20 days later. Uses Control of a wide range of annual and perennial grasses (including Sorghum halepense, Agropyron repens and Cynodon dactylon) in soya beans, cotton, sugar beet, potatoes, peanuts, peas, oilseed rape and vegetables, at 60-200 g/ha. Phytotoxicity Occasionally soya beans and peas may show some chlorotic and necrotic spots on treated leaves at higher dosage rates; this does not affect further vegetative growth or yield. Formulation types EC. Selected products: 'Agil' (Makhteshim-Agan); 'Claxon' (Makhteshim-Agan)

OTHER PRODUCTS
'Correct' (Makhteshim-Agan); 'Falcon' (Makhteshim-Agan); 'PQF 100' (Landgold); 'Satchmo' (GreenCrop); 'Shogun' (Makhteshim-Agan)

ANALYSIS
Product analysis by hplc. Residues determined by hplc or by gc with ECD.

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for rats >5000, mice 3009 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. Non-irritant to skin and eyes (rabbits). No allergic sensitisation in open epicutaneous test (guinea pigs); sensitising in maximisation test. Inhalation LC50 (4 h) for rats >2.5 mg/l air. NOEL (2 y) for rats and mice 1.5 mg/kg b.w. daily; (1 y) for dogs 20 mg/kg b.w. daily. ADI 0.015 mg/kg b.w. Other Not mutagenic, not teratogenic, no reproduction effects. Toxicity class WHO (a.i.) U EC classification (R43)

ECOTOXICOLOGY
Birds LD50 for bobwhite quail >2000, mallard ducks >2198 mg/kg. Dietary LC50 (5 d) for mallard ducks and bobwhite quail >6593 ppm. Fish LC50 (96 h) for rainbow trout 1.2, carp 0.19, bluegill sunfish 0.34 mg/l. Daphnia EC50 (48 h) >2.1 mg/l. Algae EC50 (96 h) for Selenastrum capricornutum >2.1 mg/l. Other aquatic spp. NOEC (7 d) for Lemna gibba 1.5 mg/l. Bees LD50 (48 h) (oral) >20 mg/bee; (contact) >200 mg/bee. Worms LC50 (14 d) >1000 mg/kg soil. Other beneficial spp. No risk to beneficial arthropods (e.g. Typhlodromus pyri and Aphidius rhopalosiphi) or to soil micro-organisms, at normal application rates.

ENVIRONMENTAL FATE
Animals After oral administration, propaquizafop was rapidly absorbed and excreted mainly in faeces and urine. Elimination half lives 15.6-27.2 hours. Extensively metabolised in rats; the major metabolite in faeces and urine was the propionic acid of the parent compound, which was further oxidised and degraded by cleavage. Propaquizafop and its metabolites do not accumulate in the body tissues. Plants Plants (soya bean, sugar beet and cotton) readily take up propaquizafop through roots and leaves. The parent compound is degraded by hydrolysis to the major metabolite, the propionic acid. Soil/Environment Laboratory and field studies in aerobic soils indicate that propaquizafop was rapidly degraded by soil microorganisms; DT50 (lab, 20 °C) in various soil types <3 days; DT50 for the major metabolite 7-39 days. DT50 (field) for parent and metabolites 15-26 days after spring application. Laboratory and field studies indicated that propaquizafop and its metabolites are unlikely to accumulate in the soil or leach to ground water. In aquatic systems (water/sediment) DT50 <1 day; DT50 for the major metabolite 27-39 days.