Imidacloprid 吡虫啉

吡虫啉

吡虫啉是烟碱类超高效杀虫剂，具有广谱、高效、低毒、低残留，害虫不易产生抗性，对人、畜、植物和天敌安全等特点，并有触杀、胃毒和内吸等多重作用。害虫接触药剂后，中枢神经正常传导受阻，使其麻痹死亡。产品速效性好，药后1天即有较高的防效，残留期长达25天左右。药效和温度呈正相关，温度高，杀虫效果好。主要用于防治刺吸式口器害虫。

产品性能：
玉金刚一次拌种一季有效防治玉米整个生育期蚜虫等地下害虫的危害，具有提高发芽率，促根壮苗，防虫防病有独特功效，对玉米粗缩病效果显著，提高作物产量20%以上。

使用技术和方法：
1、用农贝得吡虫啉种子处理可分散粉剂10克兑水30-40 克搅拌，再加入10毫升赠品助剂稀释均匀。
2、将准备好的4-5斤玉米种子倒在盆内淋上药液，翻拌均匀，使每粒种子都粘上药液，阴晾一个小时即可播种。　理化性质
【通用名称】吡虫啉（英文：imidacloprid 俄文：Каптана）
其它名称 在我国的商品名称很多，如海正吡虫啉、一遍净、蚜虱净、大功臣、康复多、必林等。
【化学名称】1－（6－氯吡啶－3－吡啶基甲基）－N－硝基亚咪唑烷－2－基胺
【分 子 式】C9H10ClN5O2
【分 子 量】255.7
【理化性质】无色晶体，有微弱气味，熔点143.8℃（晶体形式1）136.4℃（形式2），蒸气压0.2μPa（20℃），密度1.543（20℃），KowlogP=0.57（22℃），溶解度水0.51g/L（20℃），二氯甲烷50-100，异丙醇1-2，甲苯0.5-1，正己烷<0.1（g/L），20℃），pH5-11稳定。　
【毒 性】大鼠急性经口LD50为1260mg/kg,急性经皮LD50>1000mg/kg。对兔眼睛和皮肤无刺激作用。
【防治对象】主要用于防治水稻、小麦、棉花等作物上的刺吸式口器害虫，如蚜虫、叶蝉、蓟马、白粉虱及马铃薯甲虫和麦秆蝇等。 蚜虫
【制 剂】 70% WS, 10% WP, 25% WP, 12.5% SL，2.5%WP
剂型 2.1%胶饵，2．5%和10%可湿性粉剂，5%乳油，20%浓可溶性粉剂。
【毒性】 低毒。

作用特点
吡虫啉是硝基亚甲基类内吸杀虫剂，是烟酸乙酰胆碱酯酶受体的作用体，干扰害虫运动神经系统使化学信号传递失灵，无交互抗性问题。用于防治刺吸式口器害虫及其抗性品系。吡虫啉是新一代氯代尼古丁杀虫剂，具有广谱、高效、低毒、低残留，害虫不易产生抗性，对人、畜、植物和天敌安全等特点，并有触杀、胃毒和内吸多重药效。害虫接触药剂后，中枢神经正常传导受阻，使其麻痹死亡。速效性好，药后1天即有较高的防效，残留期长达25天左右。药效和温度呈正相关，温度高，杀虫效果好。主要用于防治刺吸式口器害虫。
防治对象和使用方法

主要用于防治刺吸式口器害虫，如蚜虫、飞虱、粉虱、叶蝉、蓟马；对鞘翅目、双翅目和鳞翅目的某些害虫，如稻象甲、稻负泥虫、稻螟虫、潜叶蛾等也有效。但对线虫和红蜘蛛无效。可用于水稻、小麦、玉米、棉花、马铃薯、蔬菜、甜菜、果树等作物。由于它的优良内吸性，特别适于用种子处理和撒颗粒剂方式施药。一般亩用有效成分3~10克，兑水喷雾或拌种。安全间隔期20天。施药时注意防护，防止接触皮肤和吸入药粉、药液，用药后要及时用清水洗洁暴露部位。不要与碱性农药混用。不宜在强阳光下喷雾，以免降低药效。
防治绣线菊蚜、苹果瘤蚜、桃蚜、梨木虱、卷叶蛾、粉虱、斑潜蝇等害虫，可用10%吡虫啉4000～6000倍液喷雾，或用5%吡虫啉乳油2000～3000倍液喷雾。 防治蟑螂：可以选择神农2.1%灭蟑螂胶饵
最近几年的连续使用，造成了很高的抗性，在水稻上国家已经禁止使用。

种子处理使用方法（以600克/升/48%悬浮剂/悬浮种衣剂为例）　〈一〉：大粒作物
1. 花生： 40毫升兑水100-150毫升包衣30-40斤种子（1亩地种子）。.
2. 玉米：40毫升兑水100 -150毫升包衣10-16斤种子（2-3亩地种子）。
3. 小麦：40毫升兑水300-400 毫升包衣30-40斤种子（1亩地种子）。
4. 大豆：40毫升兑水20-30毫升包衣8-12斤种子（1亩地种子）。
5. 棉花：10毫升兑水50毫升包衣3斤种子（1亩地种子）
6. 其他豆类：豌豆、豇豆、菜豆、四季豆等40毫升兑水20-50毫升包衣一亩地种子。
7. 水稻：浸种10毫升每亩种量，露白后播种，尽量控制水量。

〈二〉：小粒作物
油菜、芝麻、菜籽等用40毫升兑水10-20毫升包衣2-3斤种子。
〈三〉：地下结果、块茎类作物
土豆、姜、大蒜、山药等一般用40毫升兑水3-4斤分别包衣1亩地种子。
〈四〉:移栽类作物
红薯、烟草及芹菜、葱、黄瓜、番茄、辣椒等蔬菜类作物

使用方法：
1，带营养土移栽的
40毫升，拌碎土30斤充分和营养土搅拌均匀。
2，不带营养土移栽的
40毫升水以漫过作物根部为标准。移栽前浸泡2-4小时后用剩余的水兑碎土搅拌成稀泥，再蘸根移栽。

注意事项
1、 本品不可与碱性农药或物质混用。
2、 使用过程中不可污染养蜂、养蚕场所及相关水源。
3、 适期用药，收获前两周禁止用药。
4、 如不慎食用，立即催吐并及时送医院治疗

imidacloprid
Insecticide
IRAC 4A; neonicotinoid

NOMENCLATURE
Common name imidacloprid (BSI, draft E-ISO); imidaclopride ((m) F-ISO)
IUPAC name 1-(6-chloro-3-pyridylmethyl)-N-nitroimidazolidin-2-ylideneamine
Chemical Abstracts name 1-[(6-chloro-3-pyridinyl)methyl]-N-nitro-2-imidazolidinimine
CAS RN [138261-41-3]; [105827-78-9] former number Development codes BAY NTN 33 893 (Bayer)

PHYSICAL CHEMISTRY
Mol. wt. 255.7 M.f. C9H10ClN5O2 Form Colourless crystals, with a weak characteristic odour. M.p. 144 °C V.p. 4 ´ 10-7 mPa (20 °C); 9 ´ 10-7 mPa (25 °C) KOW logP = 0.57 (21 ºC) Henry 2 ´ 10-10 Pa m3 mol-1 (20 °C, calc.) S.g./density 1.54 (23 ºC) Solubility In water 0.61 g/l (20 ºC). In dichloromethane 67, isopropanol 2.3, toluene 0.69 (all in g/l, 20 ºC); in n-hexane <0.1 g/l, (ambient temperature). Stability Stable to hydrolysis at pH 5-11.

COMMERCIALISATION
History Insecticide reported by A. Elbert et al. (Proc. Br. Crop Prot. Conf. - Pests Dis., 1990, 1, 21). Introduced in 1991 by Bayer AG and Nihon Tokushu Noyaku Seizo KK. Patents EP 0192060 Manufacturers Aimco; Bayer CropScience; Hesenta; Jiangsu Yangnong; Sharda; Tide

APPLICATIONS
Biochemistry Acts as an antagonist by binding to postsynaptic nicotinic receptors in the insect central nervous system. Mode of action Systemic insecticide with translaminar activity and with contact and stomach action. Readily taken up by the plant and further distributed acropetally, with good root-systemic action. Uses Control of sucking insects, including rice-, leaf- and planthoppers, aphids, thrips and whitefly. Also effective against soil insects, termites and some species of biting insects, such as rice water weevil and Colorado beetle. Has no effect on nematodes and spider mites. Used as a seed dressing, as soil treatment and as foliar treatment in different crops, e.g. rice, cotton, cereals, maize, sugar beet, potatoes, vegetables, citrus fruit, pome fruit and stone fruit. Applied at 25-100 g/ha for foliar application, and 50-175 g/100 kg seed for most seed treatments, and 350-700 g/100 kg cotton seed. Also used to controls fleas in dogs and cats. Formulation types DP; FS; GR; SC; SL; WG; WP; WS. Selected products: 'Admire' (USA, Japan) (Bayer CropScience); 'Confidor' (Bayer CropScience); 'Conidor' (Korea) (Bayer CropScience); 'Gaucho' (Bayer CropScience); 'Midas' (Devidayal); 'Mogambo' (Crop Health); 'Tiddo' (Tide); 'Winner' (Brazil) (Bayer CropScience); mixtures: 'Amistar Admire' (+ azoxystrobin) (Bayer CropScience); 'Baytan C' (+ triadimenol+ fuberidazole) (seed treatment) (Bayer CropScience); 'Baytan Secur' (+ triadimenol+ fuberidazole) (seed treatment) (Bayer CropScience); 'Carrena' (+ carpropamid) (Bayer CropScience); 'Chinook' (+ beta-cyfluthrin) (Makhteshim-Agan, Bayer CropScience); 'Conidan' (+ tebufenozide) (Korea) (Bayer CropScience); 'Gaucho Bl? (+ anthraquinone+ bitertanol) (Bayer CropScience); 'Gaucho M' (+ pencycuron+ thiram) (Bayer CropScience); 'Gaucho T' (+ thiram) (West Africa) (Bayer CropScience); 'Imprimo' (+ tefluthrin) (Bayer CropScience); 'Leverage' (+ cyfluthrin) (USA) (Makhteshim-Agan, Bayer CropScience); 'Monceren G' (+ pencycuron) (Germany) (Bayer CropScience); 'Prestige' (+ pencycuron) (Bayer CropScience); 'Traffic' (+ tefluthrin) (Bayer CropScience); 'Win Admire' (+ carpropamid) (Bayer CropScience)

OTHER PRODUCTS
'Advantage' (flea control) (Bayer CropScience); 'Agrofidor' (Chemvet); 'Bilogic' (Netherlands) (Bayer CropScience); 'Commando' (Vapco); 'Hachikusan' (Japan; termiticide) (Nihon Bayer); 'Intercept' (Scotts, Scotts UK); 'Lizetan' (Bayer CropScience); 'Merit' (USA, Japan) (Bayer CropScience); 'Premise' (USA, Japan; termiticide) (Bayer CropScience); 'Provado' (Bayer CropScience); 'Vaplex' (Vapco) mixtures: 'Beam Admire' (+ tricyclazole) (Japan) (Nihon Bayer); 'Cereline Secur' (+ triadimenol+ bitertanol+ fuberidazole) (UK) (Bayer CropScience); 'Cereline Secur' (+ triadimenol+ fuberidazole) (seed treatment) (Bayer CropScience); 'Confidor Supra' (+ cyfluthrin) (Makhteshim-Agan, Bayer CropScience); 'Confidor Ultra' (+ beta-cyfluthrin) (Makhteshim-Agan, Bayer CropScience); 'Gaucho Orge' (+ tebuconazole+ triazoxide) (seed treatment, France, Belgium) (Bayer CropScience); 'Gaucho Rx 246 FS' (+ tebuconazole) (seed treatment, Sudan, Ethiopia, Latin America) (Bayer CropScience); 'Gaucho XT' (+ metalaxyl+ tebuconazole) (Gustafson); 'Legend' (+ cyfluthrin) (Makhteshim-Agan, Bayer CropScience); 'Manta Plus' (+ triadimenol+ fuberidazole+ imazalil) (Germany) (Bayer CropScience); 'Monceren Admire' (+ pencycuron) (Bayer CropScience); 'Monceren Star' (+ pencycuron) (Bayer CropScience); 'Montur' (+ tefluthrin) (Bayer CropScience); 'Raxil Secur' (+ tebuconazole+ triazoxide) (seed treatment, UK) (Bayer CropScience); 'Sibutol Secur' (+ bitertanol+ fuberidazole) (UK) (Bayer CropScience); 'Vget Admire' (+ tiadinil) (Nihon Nohyaku) Discontinued products: 'Premier' * (Brazil) (Bayer) mixtures: 'Ferial Bl? * (+ anthraquinone+ bitertanol) (Bayer); 'Ferial Orge' * (+ tebuconazole+ triazoxide) (seed treatment, France) (Bayer); 'Poncho' * (+ beta-cyfluthrin) (Bayer); 'Taifun' * (+ methamidophos) (Turkey) (Bayer)

ANALYSIS
Product analysis by rplc (AOAC Methods, 17th Ed., 997.12). Residues by hplc (CIPAC Handbook, 1998, H, 185; F-J. Placke & E. Weber, Pflanzenschutz-Nachrich. Bayer,93/2, 46, 109-182 (1993)). A method has been developed based on the presence of the 6-chloropyridinylmethylene moiety in all known plant and animal metabolites.

MAMMALIAN TOXICOLOGY
Reviews FAO/WHO 92, 94 (see part 2 of the Bibliography). Oral Acute oral LD50 for male and female rats c. 450 mg/kg. Skin and eye Acute percutaneous LD50 (24 h) for rats >5000 mg/kg. Non-irritating to eyes and skin (rabbits). Not a skin sensitiser. Inhalation LC50 (4 h) for rats >5323 mg/m3 dust, 69 mg/m3 air (aerosol). NOEL (2 y) for male rats 100, female rats 300, mice 330 mg/kg diet; (52 w) for dogs 500 mg/kg diet. ADI (JMPR) 0.06 mg/kg b.w. [2001] Other Not mutagenic or teratogenic. Toxicity class WHO (a.i.) II; EPA (formulation) II

ECOTOXICOLOGY
Birds Acute oral LD50 for Japanese quail 31, bobwhite quail 152 mg/kg. Dietary LC50 (5 d) for bobwhite quail 2225, mallard ducks >5000 mg/kg. Fish LC50 (96 h) for golden orfe 237, rainbow trout 211 mg/l. Daphnia LC50 (48 h) 85 mg/l. Algae ErC50 (72 h) for Pseudokirchneriella subcapitata >100 mg/l. Bees Harmful to honeybees by direct contact, but no problems expected when not sprayed into flowering crop or when used as a seed treatment. Worms LC50 for Eisenia foetida 10.7 mg/kg dry soil.

ENVIRONMENTAL FATE
Animals After oral administration of methylene-14C- and 4,5-imidazolidine-14C-labelled imidacloprid to rats, the radioactivity was quickly and almost completely absorbed from the gastro-intestinal tract and quickly eliminated (96% within 48 hours, mainly via the urine). Only c. 15% was eliminated as unchanged parent compound; the most important metabolic steps were hydroxylation at the imidazolidine ring, hydrolysis to 6-chloronicotinic acid, loss of the nitro group with formation of the guanidine and conjugation of the 6-chloronicotinic acid with glycine. All metabolites found in the edible organs and tissues of farm animals contained the 6-chloronicotinic acid moiety. Imidacloprid is also quickly largely eliminated from hens and goats. Plants Metabolism was investigated on rice (after soil treatment), maize (seed treatment), potatoes (granule or spray application), aubergines (granules) and tomatoes (spray treatment). In all cases, imidacloprid is metabolised by loss of the nitro group, hydroxylation at the imidazolidine ring, hydrolysis to 6-chloronicotinic acid and formation of conjugates; all metabolites contained the 6-chloropyridinylmethylene moiety. Soil/Environment In lab. studies, the most important metabolic steps were oxidation at the imidazolidine ring, reduction or loss of the nitro group, hydrolysis to 6-chloronicotinic acid and mineralisation; these processes were strongly accelerated by vegetation. Imidacloprid shows a medium adsorption to soil. Column leaching tests (with prior ageing) with a.i. and various formulations showed that imidacloprid and soil metabolites are to be classified as immobile; leaching into deeper soil layers is not to be expected if imidacloprid is used as recommended. Stable to hydrolysis under sterile conditions (under exclusion of light). Environmental DT50 c. 4 h (calc., based on tests of direct photolysis in aqueous solutions). Besides sunlight, the microbial activity of a water/sediment system is an important factor for the degradation of imidacloprid.