Imazapyr 灭草烟

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灭草烟

灭草烟属于咪唑啉酮类除草剂,是侧链氨基酸合成抑制剂,是新型广谱除草剂。本品芽后施用对莎草科杂草、一年生和多年生单子叶杂草、阔叶杂草有卓越的除草活性。

中文名称:灭草烟;3-吡啶羧酸-2-[4,5-二氢-4-甲基-4-(1-甲基乙基)-5-氧-1H-咪唑-2-基]酯 2-(4-异丙基-4-甲 灭草烟结构式
基-5-氧代-2-咪唑啉-2-基)烟酸
英文名称:2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-3-Pyridinecarboxylic acid; 2-(4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1h-imidazol-2-yl)-3-pyridine; 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinic acid; imazapyr; Imazapyr acid
通用名:灭草烟( Imazapyr)
分子式: C13H15N3O3
分子量: 320.4
化学名称: 2-(4-异丙基-4-甲基-5-氧代-2-咪唑啉-2-基)烟酸
CAS登录号: 81334-34-1

毒 性
大鼠急性经口LD50>5000mg/kg,兔急性经皮LD50>2000mg(原药)imazapyr/kg,对兔皮肤中等刺激作用,对兔眼睛的刺激是可逆的。
鱼毒LC50(96H):虹鳟、鲇鱼>100mg/L。
产 品:
95% 原药 25% 可溶性液剂

理化性质
本品的异丙铵盐为无色固体,熔点128-130℃,蒸气压0.013mPa(60℃)。溶解度(15℃):水中9.74g/L、(25℃)11.3g/L,丙酮中6g/L,乙醇中72g/L,二氯甲烷中72g/L,二甲基酰胺中473g/L,二甲基亚砜中665g/L,甲醇中230g/L,甲苯中3g/L。 Kow1.3(imazapyr)。酸性,pKa 1.9,pKa 3.6。有腐蚀性。
稳定性:imazapyr在45℃可稳定3个月,在室温下可稳定2年,在pH5-9暗处水介质中是稳定的,贮存时不能高于45℃。本品溶液在模拟日光下酸被分解,水解DT50 6天(pH5-9),土壤中DT50 90-120天。不能在无衬里的容器中混合或贮存,因其有腐蚀性。与碱或酸和强氧化剂均能很好反应。

制备
由2,3-吡啶二羧酸与乙酸酐反应生成吡啶二酸酐,再与(CH3)2CHCCH3(CN)NH2反应,产物再经水解、关环而得。

除草特点
灭草烟是一种非选择性灭生性除草剂,能迅速为杂草的根、叶吸收,通过抑制支链氨基酸的生物合成而阻止杂草生长。是一种灭生性除草剂。在土壤中的持效期较长。 适用作物 林地、非耕地。 防治对象 可以防治多数一年生和多年生的单、双子叶杂草。

应 用
本品属于咪唑啉酮类除草剂,是侧链氨基酸合成抑制剂,是新型广谱除草剂。本品芽后施用对莎草科杂草、一年生和多年生单子叶杂草、阔叶杂草有卓越的除草活性。
冬季气温低,病虫害的活动与危害大都处于隐蔽与静止状态。在冬季施用化学农药,除了选择对路农药外,还注意如下六点。一是选择晴天高温时段用药。因为害虫在冬季温度高时,其取食量与呼吸强度大于阴冷天气,药液喷洒到虫体上,被带到体内的药物也多,有利于发挥毒杀作用。
二是适当增加药量。害虫的农药致死中量不是恒定的。在常温下的温度越低,害虫的致死中量越低,所以在冬季适当增加用药量是必要的,可防害虫食药后不能死亡。农民朋友可根据气温的高低来确定用药量,但一般不超过常规用药量的50%。冬季施用农药时要严格按稀释倍数加水,不可随意加大或减少水的用量。
三是合理选用适宜冬季施用的农药。一般情况下,胃毒剂和触杀剂受温度的影响小些,内吸剂和熏蒸剂受温度的影响大些。如敌杀死、敌敌畏、乐果、甲胺磷等低温会明显影响杀虫效果。而溴氰菊酯、辛硫磷、石硫合剂等农药,在较低温下施用仍能发挥较好杀虫效果。冬季低温时节使用除草剂,其显示效果的时间比高温时间施用要长得多,因此,用药后要耐心等待,只要药液喷到了位,一般不需要新喷药。
四要延长作物的安全间隔期。冬季施用农药,农药的降解速度变慢,农药在作物体内的残荐期也相对延长,冬季防治蔬菜作物的病虫害时,应特别注意延长农药的安全间隔期,确保人体健康。
五要注意每桶稀释的药溶液水。可增添一小包“药引子”或“植物油”剂15克,或酸性的物质等,作为粘着剂。但蔬菜上施药时不可添用。
芽前和芽后使用可防除一年生和多年生阔叶杂草,以及苔草和木本植物,工业区除草用量为0.25~2.5kg/ha,橡胶园除草用量为0.125~1.0kg/ha。

 

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imazapyr
Herbicide
HRAC B WSSA 2; imidazolinone

  Imazapyr

NOMENCLATURE
imazapyr
Common name imazapyr (BSI, ANSI, draft E-ISO, (m) draft F-ISO)
IUPAC name 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinic acid
Chemical Abstracts name (?-2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-3-pyridinecarboxylic acid
CAS RN [81334-34-1] unstated stereochemistry; [94795-74-1], [108224-78-8] former numbers Development codes AC 252 925; CL 252 925 (both Cyanamid)

imazapyr-isopropylammonium
CAS RN [81510-83-0] unstated stereochemistry

PHYSICAL CHEMISTRY
imazapyr
Mol. wt. 261.3 M.f. C13H15N3O3 Form White to tan powder, with a slight odour of acetic acid. M.p. 169-173 ºC V.p. <0.013 mPa (60 ºC) KOW logP = 0.11 (22 ºC, unstated pH) Solubility In water 9.74 g/l (15 ºC), 11.3 g/l (25 ºC). In acetone 3.39, dimethyl sulfoxide 47.1, hexane 0.00095, methanol 10.5, dichloromethane 8.72, toluene 0.180 (all in g/100 ml). Stability Stable for at least 2 years at 25 ºC, 1 year at 37 ºC, and 3 months at 45 ºC. Stable in aqueous media at pH 5 to pH 9 in the dark; avoid storage >45 ºC. In solution, the acid is decomposed in simulated sunlight; DT50 6 d at pH 5 to pH 9. pKa pKa1 1.9, pKa2 3.6, pKa3 11

imazapyr-isopropylammonium
Mol. wt. 320.4 M.f. C16H24N4O3 Form Colourless solid. M.p. 128-130 ºC.

COMMERCIALISATION
History Herbicide reported by P. L. Orwick et al. (Proc. South. Weed Sci. Soc. Annu. Mtg., 36th, 1983, p. 291). Introduced by American Cyanamid Co. (now BASF AG); first marketed in 1985. Manufacturers BASF

APPLICATIONS
Biochemistry Branched chain amino acid synthesis (ALS or AHAS) inhibitor. Thus causes disruption of protein synthesis, which leads to interference in DNA synthesis and cell growth. This results in chlorosis and tissue necrosis of new leaves. Mode of action Systemic, contact and residual herbicide, absorbed by the foliage and roots, with rapid translocation in the xylem and phloem to the meristematic regions, where it accumulates. Uses Imazapyr-isopropylammonium is used for pre- and post-emergence control of annual and perennial grasses, sedges and broad-leaved weeds, as well as many brush and deciduous tree species. Used in non-crop areas, such as industrial sites, railways, roads, drainage channels, etc., at 0.25-1.7 kg/ha; in forestry management, at 0.25-1.7 kg/ha; and in plantations of rubber trees and oil palms, at 0.125-1.0 kg/ha. Phytotoxicity Non-phytotoxic to conifers. Rubber trees and oil palms show good tolerance, though application onto foliage is not selective, and care should be taken to avoid contact of the spray with the foliage of oil palms and the leaves and young bark of rubber trees. Formulation types EC; GR; SL.

imazapyr-isopropylammonium
Selected products: 'Arsenal' (BASF); 'Chopper' (BASF)

OTHER PRODUCTS
imazapyr
Mixtures: 'Lightning' (+ imazethapyr) (BASF); 'Midas' (+ MCPA-2-ethylhexyl+ imazapic) (BASF); 'OnDuty' (+ imazapic) (BASF); 'Sahara' (+ diuron) (BASF); 'Topsite' (+ diuron) (BASF)

imazapyr-isopropylammonium
'Calemba' (BASF); 'Stalker' (BASF); 'Parade' (Nomix-Chipman) mixtures: 'Onestep' (+ glyphosate-isopropylammonium) (BASF) Discontinued products: 'Assault' * (Cyanamid); 'Contain' * (Cyanamid)

ANALYSIS
Product by glc. Residues (1) in raspberries and bilberries, by glc; (2) in pine branches, leaves and on forest floors, by hplc. Details from BASF. (3) In soil, by hplc after extraction with ammonium bicarbonate and clean up (C. S. Helling & M. A. Doherty, Pestic. Sci., 45, 21-26 (1995)).

MAMMALIAN TOXICOLOGY
imazapyr
Oral Acute oral LD50 for male and female rats >5000, female mice >2000, male and female rabbits 4800 mg/kg. Skin and eye Acute percutaneous LD50 for male and female rabbits >2000, male and female rats >2000 mg/kg. Eye irritant; mild skin irritant (rabbits). No skin sensitisation (guinea pigs). Inhalation LC50 for male and female rats >5.1 mg/l air. NOEL (13 w) for rats 10 000 mg/kg b.w. (highest dose tested). No teratogenic or foetotoxic effects were observed at 1000 mg/kg b.w. in rats or 400 mg/kg b.w. in rabbits (highest doses tested). Other Acute i.p. LD50 for male rats 2500, female rats 2500-3200 mg/kg. Non-mutagenic, non-carcinogenic. Toxicity class WHO (a.i.) U; EPA (formulation) IV EC classification Xi; R36| R52, R53

imazapyr-isopropylammonium
Oral Acute oral LD50 >1130 mg/kg a.e. (as 226 g/kg formulation with surfactant). Skin and eye Acute percutaneous LD50 for mice >2000 mg tech./kg.

ECOTOXICOLOGY
imazapyr
Birds Acute oral LD50 for bobwhite quail and mallard ducks >2150 mg/kg. Dietary LC50 (8 d) for bobwhite quail and mallard ducks >5000 mg/kg. Fish LC50 (96 h) for rainbow trout, bluegill sunfish, and channel catfish >100 mg/l. Daphnia LC50 (48 h) >100 mg/l. Algae EC50 (120 h) for Selenastrum 71 mg/l, for Anabaena 11.7 mg/l, for Skeletonema 85.5 mg/l, for Navicula >59 mg/l. Bees Dermal LD50 for honeybees >100 mg/bee.

ENVIRONMENTAL FATE
Animals In rats, following oral administration, c. 87% of the dose was excreted in the urine and faeces within 24 hours. In muscle and fat tissues and blood, residual levels were <0.01 mg/kg at both 24 and 192 hours. Plants Following foliar application, residues in plants decline rapidly in the first 24 hours and are exuded from the roots into the soil. The major residue in plants is the parent compound. Soil/Environment Soil residual activity 6 months to 2 years in temperate climates, 3 to 6 months in tropical climates; the major residue is the parent compound; degradation is primarily due to soil microbial activity. In water DT50 7 days; degradation is due to photolysis. Bioaccumulation in the environment is highly unlikely.