Buprofezin 噻嗪酮

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噻嗪酮

理化性质及简介
噻嗪酮(扑虱灵)
通用名称:噻嗪酮
英文通用名称:buprofezin
化学名称:2-特丁基亚氨基-3-异丙基-5-苯基-1,3,5-噻二嗪-4-酮;
分 子 式:C16H23N3OS
分子量:305.4
理化性质:
外观 白色晶体(工业品为白色至浅黄色晶状粉末)。
熔点:104.5-105.5℃。
蒸气压:1.25mPa(25℃)。
密度:1.18(20℃)。
溶解性:水中为9mg/L(20℃),氯仿中520g/L,苯中370g/L,甲苯中320g/L,丙酮中240g/L,乙醇中80g/L,己烷中20g/L(均为25℃)。
稳定性:对酸和碱稳定,对光和热稳定。
制剂:25%乳油;25%可湿性粉剂;40%胶悬剂.

制法
1.特丁基异硫氰酸酯的制备
将74.1g叔丁醇,600ml水,95.1g硫氰酸铵混合后,升温到75°C,冷凝器有回流时,在30MIN内将200ml30%盐酸滴加到反应液中,然后升温到85°C,保温5H。反应液降温至30°C,静置,分出水层,油层水洗,得到103g,减压收集80°C/16kPa馏分98.5g
2.N-特丁基-N`-异丙基硫脲的制备
将24.8g特丁基异硫氰酸酯和70ml甲苯混合后,反应液冷却到10°C,搅拌下将13.1g异丙胺滴加到反应液中,反应温度不超过20°C,在室温下搅拌2H滤,用甲苯洗涤,干燥
3.N,N-甲基-苯基甲酰胺的制备
将85.6g N-甲基苯胺,56.0g(85%含量)甲酸,150ml甲苯升温回流3~4H共沸脱水,使回流液透明为止。减压下尽可能把过量的甲苯,甲酸蒸出,得粗品110g,减压收集110~113°C/0.8~0.9kPa,馏分98g
4.N,N-氯甲基-苯基氨基甲酰氯的制备
将76.8g N,N-甲基-苯基甲酰胺,500ml四氯化碳在搅拌的情况下通入氯气,并控制反应温度在15MIN出现回流,,通氯气1H至100g。蒸出四氯化碳,得到粗品油状物108g
工业采用 N-甲基苯胺与光气,氯气反应制造N,N-氯甲基-苯基氨基甲酰氯
5.噻嗪酮的合成
将11.5g N,N-氯甲基-苯基氨基甲酰氯溶于10ml甲苯溶液,滴加到由氢氧化钠,甲苯,和9.0g N-特丁基-N`-异丙基硫脲组成的反应中,控制反应温度不超过25°C,然后在室温下搅拌3H,静置,分出水层。有机相减压脱除甲苯,残留物加甲醇60ml冷却到-5~0°C,抽滤,得到干燥产物10.8g

作用特点
是一种杂环类昆虫几丁质合成抑制剂,破坏昆虫的新生表皮形成,干扰昆虫的正常生长发育,引起害虫死亡。具触杀、胃毒作用强,具渗透性。不杀成虫,但可减少产卵并阻碍卵孵化。
药效慢,药后3-7天才能达到药剂高峰。

主要应用
应用:本品为对鞘翅目、部分同翅目以及蜱螨目具有持效性杀幼虫活性的杀虫剂。可有效地防治水稻上的大叶蝉科、飞虱科;马铃薯上的大叶蝉科;柑桔、棉花和蔬菜上的粉虱科;柑桔上的蚧科、盾蚧料和粉蚧科。
适用作物:水稻、果树、茶树、蔬菜
防治对象:
本品对同翅目的飞虱、叶蝉、粉虱及介壳虫类害虫有特效。
施药技术:
●水稻害虫:稻飞虱、叶蝉类,每亩用25%可湿性粉剂20~30g兑水50~75公斤喷雾。
●果树害虫:柑桔矢尖蚧、黑刺粉虱等用25%WP1500~2000倍液喷雾。
●茶树害虫:茶小绿叶蝉用25%可湿粉750~1500倍液喷雾。
●蔬菜害虫:白粉虱等用25%可湿粉1500~2000倍液喷雾。
注意事项:
●本品不可用毒土法。
●药液不能直接与白菜、萝卜接触,否则会出现褐斑及绿叶白化等药害症状。
分析方法:气相色谱法

剂型:
噻嗪酮 10%EC
噻嗪酮 25%WP
噻嗪酮 50%SC
噻嗪酮 70%WDG

残留标准
蔬菜:2005年1月17日,美国公布了两项关于修改噻嗪酮残留限量的法规。法规涉及的产品包括部分水果和蔬菜。法规分别对以下食品内或表面的杀虫剂噻嗪酮(Bruprofezin)制定如下限量:莴苣头:5.0ppm;莴苣叶:13.0ppm;蔬菜、蔬菜用葫芦9组:0.50ppm;水果、柑橘10组:2.5ppm;柑橘的干果肉7.5ppm;柑橘油:80ppm。
茶叶:欧盟对噻嗪酮残留的最大限量定为0.05mg/kg,中国对噻嗪酮残留的最大残留限量为10mg/kg。

 

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buprofezin
Insecticide, acaricide
IRAC 16

  Buprofezin

NOMENCLATURE
Common name buprofezin (BSI, draft E-ISO); buprofézine ((f) draft F-ISO)
IUPAC name 2-tert-butylimino-3-isopropyl-5-phenyl-1,3,5-thiadiazinan-4-one
Chemical Abstracts name 2-[(1,1-dimethylethyl)imino]tetrahydro-3-(1-methylethyl)-5-phenyl-4H-1,3,5-thiadiazin-4-one
CAS RN [69327-76-0] Development codes NNI-750 (Nihon Nohyaku)

PHYSICAL CHEMISTRY
Composition Tech. is 99.1%. Mol. wt. 305.4 M.f. C16H23N3OS Form White crystals; (tech., white or pale yellow crystalline powder). M.p. 104.5-105.5 ºC V.p. 1.25 mPa (25 ºC) KOW logP = 4.3 Henry 4.24 ´ 10-1 Pa m3 mol-1 (calc.) S.g./density 1.18 (20 °C) Solubility In water 0.9 mg/l (25 ºC). In chloroform 520, benzene 370, toluene 320, acetone 240, ethanol 80, hexane 20 (all in g/l, 25 ºC). Stability Stable in acidic and alkaline media. Stable to heat and light.

COMMERCIALISATION
History Insecticide reported by H. Kanno et al. (Proc. Br. Crop Prot. Conf. - Pests Dis., 1981, 1, 59). Introduced by Nihon Nohyaku Co., Ltd in 1984. Manufacturers Nihon Nohyaku

APPLICATIONS
Biochemistry Probable chitin synthesis and prostaglandin inhibitor. Hormone disturbing effect, leading to suppression of ecdysis. Mode of action Persistent insecticide and acaricide with contact and stomach action; not translocated in the plant. Inhibits moulting of nymphs and larvae, leading to death. Also suppresses oviposition by adults; treated insects lay sterile eggs. Uses Insecticide with persistent larvicidal action against Homoptera, some Coleoptera and also Acarina. Effective against Cicadellidae, Deltocephalinae (leafhoppers) and Delphacidae (planthoppers) in rice, at 50-250 g/ha; Cicadellidae (lady beetle) in potatoes; Aleyrodidae (whitefly) in citrus, cotton and vegetables, at 0.025-0.075 g/ha; Coccidae, Diaspididae (scale insects) and Pseudococcidae (mealybugs) in citrus and top fruit, at 25-50 g/hl; Tarsonemidae in vegetables, at 250-500 g/ha. Suitable for IPM programmes. Phytotoxicity Slightly phytotoxic to Chinese cabbage. Formulation types DP; GR; SC; WP. Selected products: 'Applaud' (Nihon Nohyaku); 'Maestro' (Cequisa); 'Profezon' (Vapco); 'Viappla' (Vipesco)

OTHER PRODUCTS
'Accolade' (Bayer CropScience); 'Geiser' (AFRASA) mixtures: 'Fuji-One Applaud Limber' (+ furametpyr+ isoprothiolane) (Nihon Nohyaku); 'Dadeci' (+ deltamethrin) (Bayer CropScience) Discontinued products mixtures: 'Karapp' * (+ lambda-cyhalothrin) (Zeneca)

ANALYSIS
Product by glc. Residues in soil and rice plants and water, by glc with ECD (M. Uchida et al., J. Pestic. Sci., 7, 397 (1982)); in crops, by glc with NPD (H. Nishizawa et al., J. AOAC International, 77, 1631 (1994)). Details from Nihon Nohyaku.

MAMMALIAN TOXICOLOGY
Reviews FAO/WHO 86 (see part 2 of the Bibliography). Oral Acute oral LD50 for male rats 2198, female rats 2355, male and female mice >10 000 mg/kg. Skin and eye Acute percutaneous LD50 for rats >5000 mg/kg. Mild skin irritant (guinea pigs); not irritating to skin and eyes (rabbits). Inhalation LC50 (4 h) for rats >4.57 mg/l air. NOEL for male rats 0.90, female rats 1.12 mg/kg daily. ADI (JMPR) 0.01 mg/kg [1999]. Other Non-carcinogenic, non-mutagenic. Toxicity class WHO (a.i.) U; EPA (formulation) III

ECOTOXICOLOGY
Fish LC50 (48 h) for carp 2.7, rainbow trout >1.4 mg/l. Daphnia LC50 (3 h) for D. pulex 50.6 mg/l. Bees No direct effect at 2000 mg/l (WP formulation). Other beneficial spp. No effect on various predators (Euseius stipulatus 250 mg/l; Phytoseiulus persimilis 500 mg/l; Cyrtorhinus lividipennis, Microvelia atrolineata 250 mg/l; Lycosa pseudoannulata 2000 mg/l) or parasites (Aphytis lingnanensis 125 mg/l; Cales noacki, Encarsia formosa, Paracentrobia andoi 250 mg/l; Ephedrus japonicus 1000 mg/l).

ENVIRONMENTAL FATE
Animals Low residues were found in nearly all ruminant and poultry tissues. Extensive metabolism was observed, with a large number of minor metabolites being produced Plants Limited metabolism in most plant species; minor metabolites indicate a pathway involving hydroxylation or oxidative loss of the tert-butyl group, followed by opening of the heterocyclic ring. Soil/Environment DT50 (25 °C) 104 d (flooded conditions, silty clay loam, o.c. 3.8%, pH >6.4), 80 d (upland conditions, sandy loam, o.c. 2.4%, pH 7.0) (J. Pestic. Sci., 11, 605-610 (1986)).