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(R)-α-cyano-3-phenoxybenzyl trans-3-(2,2-dichlorovinyl)-2,2-dimethyl-cycloprpanecarboxylate | 67375-30-8

中文名称
——
中文别名
——
英文名称
(R)-α-cyano-3-phenoxybenzyl trans-3-(2,2-dichlorovinyl)-2,2-dimethyl-cycloprpanecarboxylate
英文别名
(R)-α-cyano-3-phenoxybenayl-trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylate;trans-αR-cypermethrin;(R)-theta-CYP;(R)-theta-cypermethrin;(1S,3S)-(R)-Cyano(3-phenoxyphenyl)methyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate;[(R)-cyano-(3-phenoxyphenyl)methyl] 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
(R)-α-cyano-3-phenoxybenzyl trans-3-(2,2-dichlorovinyl)-2,2-dimethyl-cycloprpanecarboxylate化学式
CAS
67375-30-8
化学式
C22H19Cl2NO3
mdl
——
分子量
416.304
InChiKey
KAATUXNTWXVJKI-FDYSRKEFSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 熔点:
    78-81°C
  • 沸点:
    200°C (rough estimate)
  • 密度:
    1.12
  • 闪点:
    100 °C
  • 溶解度:
    可溶于氯仿(少许)、甲醇(少许)
  • 颜色/状态:
    Viscous yellowish brown semisolid mass.
  • 蒸汽压力:
    1.73X10-5 mm Hg @ 20 °C
  • 稳定性/保质期:
    Very stable in neutral and acidic media. Hydrolyzed in strongly alkaline media. Thermally stable up to 220 °C. Field data indicate that in practice it is stable to air and light.

计算性质

  • 辛醇/水分配系数(LogP):
    6
  • 重原子数:
    28
  • 可旋转键数:
    7
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.27
  • 拓扑面积:
    59.3
  • 氢给体数:
    0
  • 氢受体数:
    4

ADMET

代谢
...基本上,除虫菊素和丙烯菊酯主要通过氧化酸部分中的异丁烯基侧链和醇部分中的不饱和侧链以及酯水解来分解,而在其他拟除虫菊酯中,酯水解占主导地位。/除虫菊素和拟除虫菊酯/
The metabolic pathways for the breakdown of the pyrethroids vary little between mammalian species but vary somewhat with structure. ... Essentially, pyrethrum and allethrin are broken down mainly by oxidation of the isobutenyl side chain of the acid moiety and of the unsaturated side chain of the alcohol moiety with ester hydrolysis playing and important part, whereas for the other pyrethroids ester hydrolysis predominates. /Pyrethrum and pyrethroids/
来源:Hazardous Substances Data Bank (HSDB)
代谢
哺乳动物对拟除虫菊酯的相对抗性几乎完全归因于它们能够迅速将拟除虫菊酯水解为其不活跃的酸和醇成分,因为直接注射到哺乳动物的中央神经系统会导致与昆虫中看到的相似易感性。恒温生物的一些额外抗性也可以归因于拟除虫菊酯的作用负温度系数,这意味着在哺乳动物体温下毒性较低,但主要效果是代谢性的。拟除虫菊酯的代谢消除非常迅速,这意味着通过静脉注射的毒性很高,通过较慢的口服吸收毒性适中,而通过皮肤吸收的毒性通常很低。/拟除虫菊酯/
The relative resistance of mammals to the pyrethroids is almost wholly attributable to their ability to hydrolyze the pyrethroids rapidly to their inactive acid & alcohol components, since direct injection into the mammalian CNS leads to a susceptibility similar to that seen in insects. Some additional resistance of homeothermic organisms can also be attributed to the negative temperature coefficient of action of the pyrethroids, which are thus less toxic at mammalian body temperatures, but the major effect is metabolic. Metabolic disposal of the pyrethroids is very rapid, which means that toxicity is high by the iv route, moderate by slower oral absorption, & often unmeasureably low by dermal absorption. /Pyrethroids/
来源:Hazardous Substances Data Bank (HSDB)
代谢
最快的水解和氧化攻击发生在具有反式取代基的初级醇酯上。对于所有的次级醇酯和初级醇顺式取代的环丙烷甲酸酯,氧化攻击是主要的。/拟除虫菊酯/
FASTEST BREAKDOWN IS SEEN WITH PRIMARY ALCOHOL ESTERS OF TRANS-SUBSTITUTED ACIDS SINCE THEY UNDERGO RAPID HYDROLYTIC & OXIDATIVE ATTACK. FOR ALL SECONDARY ALCOHOL ESTERS & FOR PRIMARY ALCOHOL CIS-SUBSTITUTED CYCLOPROPANECARBOXYLATES, OXIDATIVE ATTACK IS PREDOMINANT. /PYRETHROIDS/
来源:Hazardous Substances Data Bank (HSDB)
代谢
拟除虫菊酯在摄入后据报道会在胃肠道中被灭活。在动物体内,拟除虫菊酯会迅速代谢成水溶性、无活性的化合物。
Pyrethrins are reportedly inactivated in the GI tract following ingestion. In animals, pyrethrins are rapidly metabolized to water soluble, inactive compounds. /Pyrethrins/
来源:Hazardous Substances Data Bank (HSDB)
代谢
拟除虫菊酯通常通过哺乳动物的酯水解、氧化和结合进行代谢,并且没有在组织中积累的趋势。在环境中,拟除虫菊酯在土壤和植物中相当迅速地降解。分子上各个位点的酯水解和氧化是主要的降解过程。
Synthetic pyrethroids are generally metabolized in mammals through ester hydrolysis, oxidation, and conjugation, and there is no tendency to accumulate in tissues. In the environment, synthetic pyrethroids are fairly rapidly degraded in soil and in plants. Ester hydrolysis and oxidation at various sites on the molecule are the major degradation processes. /Synthetic pyrethroids/
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 毒性总结
标识:Alpha-氯菊酯是一种高活性的拟除虫菊酯类杀虫剂,对农业和畜牧业中遇到的广泛害虫有效。它以乳油、超低容量制剂、悬浮剂形式提供,并与其他杀虫剂混合使用。技术产品是一种结晶性粉末,易溶于丙酮、环己酮和二甲苯,但在水中的溶解性较低。它在酸性和中性条件下稳定。人类暴露:一般来说,如果按照良好的农业实践使用Alpha-氯菊酯,普通人群的暴露是可以忽略的。通过良好的工作实践、卫生措施和安全预防措施,使用Alpha-氯菊酯对职业暴露的人来说不太可能构成危险。面部感觉的出现是暴露的迹象。在这种情况下,应审查工作实践。动物研究:Alpha-氯菊酯对啮齿动物的急性口服毒性为中等至高。急性口服暴露会导致与中枢神经系统活动相关的临床体征。技术Alpha-氯菊酯被报告为对兔皮肤有轻微刺激性。某些配方会导致严重的眼部刺激。在豚鼠中,Alpha-氯菊酯引起皮肤感觉神经末梢的刺激。在大鼠的口服研究中,Alpha-氯菊酯通过坐骨神经和腓肠神经的病理学改变、轴突退化和β-半乳糖苷酶活性增加而引起神经毒性。目前还没有关于长期毒性、生殖毒性、致畸性、免疫毒性和致癌性的数据。根据现有的Alpha-氯菊酯数据,可以得出结论,这种化合物在沙门氏菌、大肠杆菌和酿酒酵母的测试中,以及在大鼠肝细胞体内和体外诱导染色体畸变和产生DNA单链损伤的测试中都是非致突变性的。Alpha-氯菊酯对水生无脊椎动物、鱼类和蜜蜂高度有毒。
IDENTIFICATION: Alpha-cypermethrin is a highly active pyrethroid insecticide, effective against a wide range of pests encountered in agriculture and animal husbandry. It is supplied as emulsifiable concentrate, ultra-low-volume formulation, suspension concentrate and in mixtures with other insecticides. The technical product is a crystalline powder with good solubility in acetone, cyclohexanone and xylene, but its solubility in water is low. It is stable under acidic and neutral conditions. HUMAN EXPOSURE: Exposure of the general population to alpha-cypermethrin is negligible, provided its use follows good agricultural practice. With good work practices, hygiene measures, and safety precautions, the use of alpha-cypermethrin is unlikely to present a hazard to those occupationally exposed to it. The occurrence of "facial sensations" is an indication of exposure. Under these circumstances work practices should be reviewed. ANIMAL STUDIES: Alpha-cypermethrin has moderate to high acute oral toxicity to rodents. Acute oral exposure results in clinical signs associated with central nervous system activity. Technical alpha-cypermetrhrin has been reported to be minimally irritating to rabbit skin. Some formulations cause severe eye irritations. In guinea-pigs, alpha-cypermethrin caused stimulation of sensory nerve-endings in the skin. An oral study in rats demonstrated that alpha-cypermethrin induces neurotoxicity due to histopathological alterations of the tibial and sciatic nerves, axonal degeneration and increased beta-galactosidase activity. No data are available on long-term toxicity, reproductive toxicity, teratogenicity, immunotoxicity, or carcinogenicity. From the available data on alpha-cypermethrin, it can be concluded that this compound is non-mutagenic in tests with Salmonella typhimurium, Escherichia coli and Saccharomyces cerevisiae, and in vivo and in vitro tests with rat liver cells for the induction of chromosome aberration and production of DNA single-strand damage. Alpha-cypermethrin is highly toxic to aquatic invertebrates, fish, and bees.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 副作用
神经毒素 - 其他中枢神经系统神经毒素
Neurotoxin - Other CNS neurotoxin
来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
毒理性
  • 毒性数据
LC50(大鼠)> 400 mg/m³/4h
LC50 (rat) > 400 mg/m3/4h
来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
毒理性
  • 相互作用
拟除虫菊酯类农药解毒……在苍蝇中很重要,可能因添加增效剂……如有机磷或氨基甲酸酯……而延迟……以确保致死效果。……拟除虫菊酯类农药
/Pyrethroid/ detoxification ... important in flies, may be delayed by the addition of synergists ... organophosphates or carbamates ... to guarantee a lethal effect. ... /Pyrethroid/
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 相互作用
增效醚通过抑制负责在节肢动物体内代谢除虫菊酯的水解酶,从而增强除虫菊酯的杀虫活性。当增效醚与除虫菊酯联合使用时,后者的杀虫活性可增强2-12倍。
Piperonyl butoxide potentiates /insecticidal activity/ of pyrethrins by inhibiting the hydrolytic enzymes responsible for pyrethrins' metab in arthropods. When piperonyl butoxide is combined with pyrethrins, the insecticidal activity of the latter drug is increased 2-12 times /Pyrethrins/
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
1. 对赛百灵(作为1:1顺/反混合物)和顺赛百灵(构成顺赛百灵的两个灾难对映体之一)的排泄研究分别在每个剂量水平上对两名志愿者进行了研究。这些研究包括:(a)单次口服顺赛百灵剂量为0.25毫克、0.50毫克和0.75毫克,随后在相同的水平上重复口服顺赛百灵剂量,每天一次,连续五天;(b)重复口服赛百灵剂量为0.25毫克、0.75毫克和1.5毫克,每天一次,连续五天;以及(c)在手臂上单次涂抹25毫克赛百灵。在给药前后监测尿液中自由和结合的3-(2,2-二氯乙烯基)-2,2-二甲基环丙烷羧酸。2. 单次口服顺赛百灵的代谢和排泄速率与顺赛百灵相似,平均而言,约43%的剂量在首次24小时尿液中以环丙烷羧酸的形式排出。当顺赛百灵作为重复口服剂量给药时,尿液中代谢物排泄量没有增加。受试者在给药后的后续24小时周期内,平均将剂量的49%以环丙烷羧酸的形式排出。3. 当赛百灵作为重复口服剂量给药时,尿液中环丙烷羧酸的排泄量没有增加。受试者在给药后的后续24小时周期内,平均将反式异构体剂量的72%和顺式异构体剂量的45%分别排出。4. 大约0.1%的涂抹皮肤剂量25毫克赛百灵在72小时内以尿液中环丙烷羧酸的形式排出。从这样的尿液排泄数据中无法得出赛百灵及其代谢物在皮肤或其他器官中的浓度,或存在其他代谢或排泄途径的可能性。
1. Dose excretion studies with cypermethrin (as a 1:1 cis/trans mixture) and alphacypermethrin (one of the two disasteroisomer pairs which constitute cis-cypermethrin) were out with, in each case, two volunteers per dose level. The studies included (a) single oral alphacypermethrin doses of 0.25 mg, 0.50 mg and 0.75 mg followed by repeated alphacypermethrin doses at the same levels, daily for five days, (b) repeated oral cypermethrin doses of 0.25 mg, 0.75 mg and 1.5 mg daily for five days, and (c) a single dermal application of 25 mg cypermethrin to the forearm. Urine was monitored for the free and conjugated 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid before and after dosing. 2. Metabolism and rate of excretion of a single oral dose of alphacypermethrin was similar to that of cis cypermethrin, on average, 43% of the dose was excreted as the cyclopropanecarboxylic acid in the first 24 hr urine. There was no increase in urinary metabolite excretion when alphacypermethrin was administered as a repeated oral dose. Subjects excreted, on average, 49% of the dose as the cyclopropanecarboxylic acid in the subsequent 24 hr periods after dosing. 3. There was no increase in the urinary cyclopropanecarboxylic acid excretion when cypermethrin was administered as a repeated oral dose. Subjects excreted, on average, 72% of the trans isomer dose and 45% of the cis isomer dose respectively in the subsequent 24 hr periods after dosing. 4. Approximately 0.1% of the applied dermal dose of 25 mg cypermethrin was excreted within 72 hr as the urinary cyclopropanecarboxylic acid. No conclusions can be drawn from such urinary excretion data as to the concentration of cypermethrin and its metabolites in the skin or other organs, or the possibility of other routes of metabolism or excretion.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
/PYRETHROIDS/迅速渗透昆虫外壳,正如通过触杀LD50对美洲大蠊(蟑螂)的实验所显示的那样... /PYRETHROIDS/
/PYRETHROIDS/ READILY PENETRATE INSECT CUTICLE AS SHOWN BY TOPICAL LD50 TO PERIPLANETA (COCKROACH) ... /PYRETHROIDS/
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
当放射性拟除虫菊酯通过口服给予哺乳动物时,它会被动物的小肠吸收并分布到所有被检查的组织中。给予大鼠转位异构体的放射性排泄情况如下:剂量:500毫克/千克;间隔:20天;尿液:36%;粪便:64%;总计:100%。/拟除虫菊酯/
WHEN RADIOACTIVE PYRETHROID IS ADMIN ORALLY TO MAMMALS, IT IS ABSORBED FROM INTESTINAL TRACT OF THE ANIMALS & DISTRIBUTED IN EVERY TISSUE EXAMINED. EXCRETION OF RADIOACTIVITY IN RATS ADMIN TRANS-ISOMER: DOSAGE: 500 MG/KG; INTERVAL 20 DAYS; URINE 36%; FECES 64%; TOTAL 100%. /PYRETHROIDS/
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
拟除虫菊酯通过完整皮肤局部应用时可以被吸收。当动物接触到含有胡椒基丁氧基的拟除虫菊酯气溶胶时,这种混合物几乎没有或没有系统性吸收。/拟除虫菊酯/
Pyrethrins are absorbed through intact skin when applied topically. When animals were exposed to aerosols of pyrethrins with piperonyl butoxide being released into the air, little or none of the combination was systemically absorbed. /Pyrethrins/
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
尽管有限的吸收可能是某些拟除虫菊酯类低毒性的原因,但通过哺乳动物肝脏酶(酯水解和氧化)的快速生物降解可能是主要负责的因素。大多数拟除虫菊酯代谢物会迅速被肾脏至少部分排出。/拟除虫菊酯/
Although limited absorption may account for the low toxicity of some pyrethroids, rapid biodegradation by mammalian liver enzymes (ester hydrolysis and oxidation) is probably the major factor responsible. Most pyrethroid metabolites are promptly excreted, at least in part, by the kidney. /Pyrethroids/
来源:Hazardous Substances Data Bank (HSDB)

安全信息

  • 危险等级:
    6.1(b)
  • 危险品标志:
    T
  • 安全说明:
    S36/37/39,S45,S60,S61
  • 危险类别码:
    R48/22,R25,R50/53,R37
  • WGK Germany:
    3
  • 危险品运输编号:
    UN 2811
  • RTECS号:
    GZ1250000
  • 包装等级:
    III
  • 危险类别:
    6.1(b)

SDS

SDS:49847e56bf69de7dac6ca57605b79ceb
查看

制备方法与用途

化学性质
纯品为白色至奶油色结晶,熔点80.5℃,相对密度1.12,在20℃时的蒸气压为170×10^-6帕。易溶于醇类、酮类及芳香烃类有机溶剂,如环己酮515g/L和二甲苯315g/L,在水中的溶解度约为5~10mg/L(即每升水中可溶解约0.01~0.2mg)。在酸性及中性条件下较为稳定,在强碱性环境下易水解,热稳定性良好。

用途
氯氰菊酯高效异构体具有触杀和胃毒作用,杀虫谱广,击倒速率快,生物活性高。主要用于防治棉花、蔬菜、果树、茶叶上的多种作物害虫及卫生害虫。例如:

  • 防治棉蚜:使用4.5%乳油336~666mL(有效成分15~30g)/hm²,兑水600~700L均匀喷雾。
  • 防治棉铃虫、棉红铃虫在二、三代卵孵盛期:使用4.5%乳油336~666mL(有效成分15~30g)/hm²,兑水750~900L均匀喷雾。
  • 防治菜蚜、菜青虫、小菜蛾:使用4.5%乳油200~560mL(有效成分9~25g)/hm²,兑水600~750L均匀喷雾。
  • 防治家蝇及蚊子:每平方米用4.5%可湿性粉剂0.2~0.4g(有效成分9~18mg),兑水250倍液喷雾。
  • 防治蟑螂:每平方米使用4.5%可湿性粉剂0.9g(有效成分40.5mg),兑水250~300倍液喷洒。

用途
广泛用于防治棉花、果树、大豆、蔬菜等作物上的鳞翅目、鞘翅目和双目害虫。

生产方法
以二氯菊酸(顺反比为3/7)作为起始原料,经顺反分离后得到含量大于93%,顺反比为8/2的顺式菊酸。通过醚醛-酰氯法合成顺式氯氰菊酯,含量达到82%。再经过差向异构化过程,获得高效顺氯氰菊酯,含量高达92%,或直接从8个异构体混合物中分离出α种,并实现β体转化为α体的差向异构体过程。这一过程省去了二氯菊酸立体选择合成中的顺反异构体分离步骤。

类别
农药

毒性分级
高毒

急性毒性
口服-大鼠LD₅₀:79毫克/公斤

可燃性危险特性
易燃;燃烧产生有毒的氯化物和氮氧化物气体

储运特性
库房应通风、低温干燥,与食品原料分开储存运输

灭火剂
干粉、泡沫、砂土

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
    氯氰菊酯 cypermethrine 52315-07-8 C22H19Cl2NO3 416.304

反应信息

  • 作为产物:
    参考文献:
    名称:
    乳酸菌对θ-氯氰菊酯的立体选择性降解的影响。
    摘要:
    这项研究的目的是探讨四种影响乳酸菌(LAB)上的立体选择性降解THETA氯氰菊酯(CYP),包括植物乳杆菌,干酪乳杆菌,德氏乳杆菌和嗜热链球菌。通过纤维素三(3,5-二甲基苯基氨基甲酸酯)手性固定相的高效液相色谱法开发了一种有效的介质中(±)θ- CYP分析方法。塞塔将氯氰菊酯掺入具有不同接种率的LAB培养基中,并在0、2、8、24、36、48、72、120、168和240小时取样。结果表明,LAB影响了theta CYP对映异构体的半衰期和对映体分数,这导致2种立体异构体之间的降解速率更接近,并且在4种LAB之间没有发现明显的差异。此外,θ- CYP的立体选择性降解与pH值密切相关。pH值越低(pH值分别为3、5、7和9),对映体分数就越低(从4.88至6.69)。在3、7和9的pH值下,对映体之间的半衰期存在显着差异。(-)- θ-氯氰菊酯的下降速度快于(+)- θ- CYP在3的pH
    DOI:
    10.1002/chir.22807
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    申请人:DAINIPPON INK AND CHEMICALS, INC.
    公开号:EP0955331A2
    公开(公告)日:1999-11-10
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  • PROCEDE DE LUTTE CONTRE LES ARTHROPODES RAVAGEURS DES CULTURES ET COMPOSITION UTILE POUR CE PROCEDE
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    公开号:EP1261255B1
    公开(公告)日:2007-06-06
  • INSECTICIDAL AND MITICIDAL MIXTURES OF BIFENTHRIN AND CYANO-PYRETHROIDS
    申请人:FMC CORPORATION
    公开号:EP1962592A2
    公开(公告)日:2008-09-03
  • US6190773B1
    申请人:——
    公开号:US6190773B1
    公开(公告)日:2001-02-20
  • [EN] INSECTICIDAL AND MITICIDAL MIXTURES OF BIFENTHRIN AND CYANO-PYRETHROIDS<br/>[FR] MELANGES INSECTICIDES ET ACARICIDES CONTENANT DE LA BIFENTHRINE ET DES CYANOPYRETHROIDES
    申请人:FMC CORP
    公开号:WO2007076028A2
    公开(公告)日:2007-07-05
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