The trans-isomers as Resmethrin are metabolized mainly through hydrolysis of ester linkage with subsequent oxidation and/or conjugation of component alcohol and acid moieties. 1/3 of acid-derived metab of (+)-trans-resmethrin admin to rats were characterized and among them cis-hydroxymethyl chrysanthemumic acid and cis-chrysanthemum dicarboxylic acid were identified. (+)-cis-resmethrin yielded trans isomers of acids.
Resmethrin isomers were metabolized in microsome-NADPH systems to the extent of 95 to 98%. The extent to which trans- and cis-isomers were metabolized differed. In the presence of NADPH, ester cleavage was much greater with tetraethylpyrophosphate-treated microsomes. An oxidative ester cleavage seemed to be most important with (-)-cis-resmethrin. In the latter case, alcohol moieties released include unstable compounds and protein-bound metabolites. Seventeen precent of the initial radiocarbon appeared in 11 ester metabolites (not identified) of (+)-trans-resmethrin. These were recovered only with tetraethylpyrophosphate-treated microsomes fortified with NADPH. Oxidized chrysanthemic acid derivatives (VIII to XXII and XXVI) were comparatively stable. The metabolites IV and VII were major products only in the presence of NADPH and the supernatant fraction. Compounds II, III, V and VI were not isolated.
Some degradative products of the resmethrins are 5-benzyl-3-furoic acid, chrysanthemic acid, the intermediary alcohol and aldehyde oxidation products, and conjugates of each of these acids. The isobutenyl moiety is oxidized products, and conjugates of each of these acids. The isobutenyl moiety is oxidized at either the cis-or trans-methyl group in (+)-cis-resmethrin, but only at the trans-methyl group in (+)-trans-resmethrin. An unanticipated metabolic pathway involves epimerization at C-3 of the cyclopropane ring. Some metabolites of (+)-trans-resmethrin are more toxic than the parent compound.
When four resmethrin isomers ([1R,trans]-, [1S,trans]-, [1R,cis]-, and [1S,cis]-) were incubated with mouse and rat microsomes in 50 mmol/L tris-HCl buffer (pH 7.4) at 37 °C for 1 hr, microsomal esterases readily cleaved the trans- but not the cis-isomers. The ester linkage also appeared to undergo oxidative cleavage when esterase attack was minimal. Ester metabolites were detected in significant amounts only with [1R,cis]-resmethrin in which case oxidation had occurred at isobutenyl moiety, with or without oxidation at the benzylfuryl methyl group. Most of the in vitro metabolites were identical with those in the excreta of rats given resmethrin orally. The preferred site of oxidation in the isobutenyl moiety varies with the resmethrin isomer and microsomal source. Mouse microsomes predominantly oxidized the trans-methyl group of both [1R,trans]- and [1S,trans]- resmethrin, the selectivity, however, being the greatest with [1S,trans]-resmethrin. Rat microsomes were relatively nonselective in attacking the isobutenyl methyl groups of [1R,trans]-resmethrin.
Following ingestion, pyrethriods are hydrolysed by various digestive enzymes in the gastro-intestinal tract. However, a small portion of the insecticidally active compounds or its derivatives are absorbed, as shown by their toxicity and their effect on the liver. Pyrethriods may also be absorbed following inhalation or dermal contact. They are rapidly distributed to most tissues, particularly to those with a high lipid content, and are concentrated in central and peripheral nervous tissues. Pyrethriods or their metabolites are not known to be stored in the body or to be excreted in the milk, but no study of the matter has employed modern methods. The major metabolic pathways for pyrethriods are hydrolysis of the central ester bond, oxidative attacks at several sites, and conjugation reactions, to produce a complex array of primary and secondary water-soluble metabolites that undergo urinary excretion. Metabolism is believed to involve nonspecific microsomal carboxyesterases and microsomal mixed function oxidases, which are located in nearly all tissue types, with particularly high activities in the liver. Metabolites are excreted in the urine and faeces. (L857, L889)
Both type I and type II pyrethroids exert their effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. They appear to bind to the membrane lipid phase in the immediate vicinity of the sodium channel, thus modifying the channel kinetics. This blocks the closing of the sodium gates in the nerves, and thus prolongs the return of the membrane potential to its resting state. The repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential produces effects quite similar to those produced by DDT, leading to hyperactivity of the nervous system which can result in paralysis and/or death. Other mechanisms of action of pyrethroids include antagonism of gamma-aminobutyric acid (GABA)-mediated inhibition, modulation of nicotinic cholinergic transmission, enhancement of noradrenaline release, and actions on calcium ions. They also inhibit calium channels and Ca2+, Mg2+-ATPase. (T10, T18, L857)
来源:Toxin and Toxin Target Database (T3DB)
毒理性
致癌性证据
癌症分类：可能对人类致癌
Cancer Classification: Likely to be Carcinogenic to Humans
来源:Hazardous Substances Data Bank (HSDB)
毒理性
致癌物分类
对人类不具有致癌性（未被国际癌症研究机构IARC列名）。
No indication of carcinogenicity to humans (not listed by IARC).
Pyrethroid effects typically include rapid onset of aggressive behavior and increased sensitivity to external stimuli, followed by fine tremor, prostration with coarse whole body tremor, elevated body temperature, coma, and death. Paresthesia, severe corneal damage, hypotension and tachycardia, associated with anaphylaxis, can also occur following pyrethriod poisoning. (L857)
来源:Toxin and Toxin Target Database (T3DB)
毒理性
暴露途径
该物质可以通过吸入其气溶胶和通过吞食被吸收进人体。
The substance can be absorbed into the body by inhalation of its aerosol and by ingestion.
来源:ILO-WHO International Chemical Safety Cards (ICSCs)
The cis- & trans- isomers of the synthetic pyrethroid resmethrin, labeled with radiocarbon in either the alcohol or acid moiety, were individually admin orally to White Leghorn laying hens at 10 mg/kg. With each isomer & label position, >90% of the radiocarbon was eliminated in the excreta within 24 hr after the treatment. Radiocarbon residues in the egg white & yolk fractions were low, with peak levels observed 1 & 4-5 days after treatment in white & yolk, respectively. In birds sacrificed 12 hr after treatment, radiocarbon residues in tissues were low; the highest levels were found in the liver & kidney.
Resmethrin (insecticide) labeled with radiocarbon in either the acid or alcohol moiety & admin orally to lactating Jersey cows at 10 mg/kg was rapidly absorbed, metabolized, & excreted. The cis-isomer was eliminated primarily in the feces, but the trans-isomer was eliminated primarily in the urine. Tissue residues at 48 hr post-treatment were low (<1 ppm) except in liver & kidney which were generally higher with the alcohol labeled compounds. ...
Six days after admin of (14)C-resmethrin to rats at a dose of 1 mg/kg, 53-73% was accounted for in urine & feces. Low residue levels were observed in tissues. In urine, there were almost equal parts of free & conjugated metabolites.
When (14)C-[1RS,trans]-resmethrin labeled in the alcohol moiety was administered orally to Sprague-Dawley rats at 500 mg/kg, the radiocarbon was rapidly absorbed from the GI tract and it took 3 wk for the complete elimination of the radioactivity in the urine (36% of the dose) and feces (64%). A negligible amount (<0.1%) of the radiocarbon was expired as (14)CO2. The radiocarbon was not completely excreted, even after 2 wk, in rats given an iv dose of 50 mg/kg; notably, appreciable amounts of (14)C were found in feces.
来源:Hazardous Substances Data Bank (HSDB)
安全信息
危险等级：
9
危险品标志：
N,Xn
安全说明：
S60,S60/61,S61
危险类别码：
R22,R50/53
WGK Germany：
3
海关编码：
29321900
危险品运输编号：
3082
RTECS号：
GZ1310000
包装等级：
III
危险类别：
6.1(b)
制备方法与用途
概述
苄呋菊酯（resmethrin），又称FMC17370、NRDC104、NRDC119、OMS1206、OMS1800和SBPI382，商品名称包括Chrysron、Termout、灭虫菊。该杀虫剂的杀虫活性首次由M.Elliott等人报道，并先后被FMC Corp.、Penick Corp.和Sumitomo Chemical Co.,Ltd.等公司引入开发。苄呋菊酯为两个异构体的混合物，其中含有20%~30%（1RS）-顺式异构体和80%~70%（1RS）-反式异构体。工业品中两异构体总含量为84.5%。
[EN] ACC INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE L'ACC ET UTILISATIONS ASSOCIÉES
申请人：GILEAD APOLLO LLC
公开号：WO2017075056A1
公开（公告）日：2017-05-04
The present invention provides compounds I and II useful as inhibitors of Acetyl CoA Carboxylase (ACC), compositions thereof, and methods of using the same.
[EN] BICYCLYL-SUBSTITUTED ISOTHIAZOLINE COMPOUNDS<br/>[FR] COMPOSÉS ISOTHIAZOLINE SUBSTITUÉS PAR UN BICYCLYLE
申请人：BASF SE
公开号：WO2014206910A1
公开（公告）日：2014-12-31
The present invention relates to bicyclyl-substituted isothiazoline compounds of formula (I) wherein the variables are as defined in the claims and description. The compounds are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes. The invention also relates to a method for controlling invertebrate pests by using these compounds and to plant propagation material and to an agricultural and a veterinary composition comprising said compounds.
The present invention relates to azoline compounds of formula (I) wherein A, B1, B2, B3, G1, G2, X1, R1, R3a, R3b, Rg1 and Rg2 are as defined in the claims and the description. The compounds are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes. The invention also relates to a method for controlling invertebrate pests by using these compounds and to plant propagation material and to an agricultural and a veterinary composition comprising said compounds.
