When exposed to bromopropylate, spider mites (tetranychus urticae kock) & house flies (Musca domestica l) metabolized this material to bromine analogs of benzilic acid, benzhydrol, benzophenone, & benzoic acid.
Bromopropylate was metabolized by rat liver preparations, especially by the microsomal & the nuclear supernatant fractions. The limiting reaction was the cleavage of the ester linkage by carboxylesterases. The main metabolite was p-bromobenzoic acid.
Only the parent compound was detected in the adipose tissue and the milk of a cow which had received 0.33 mg/kg/day of 14C-labelled bromopropylate for 5 days. Most of the activity found in the feces was the parent compound as shown by analysis of the first post-treatment day sample which contained 92% parent compound, the remainder being unidentified metabolites. The majority of activity in urine consisted of 4,4'-dibromobenzilic acid and a more polar unidentified metabolite. Other possible metabolites, 4,4'-dibromobenzohydrol, 4,4'-dibromobenzophenone and 4-bromobenzoic acid were not found. In the feces of rats administered bromopropylate 60% of activity was parent compound and 20% 4,4'-dibromobenzilic acid.
The structures of 8 metabolites were identified from urine and feces, covering 80% and 72% of the dose for males and females, respectively. ...It is concluded that bromopropylate was metabolized preferentially by cleavage of the isopropyl ester and to a minor extent by oxidation reactions attacking the phenyl ring and the isopropyl group. The primary product formed after ester cleavage, the benzilic acid, was subject to subsequent conjugation reactions, leading to a variety of amino acid conjugates, or was excreted as such. Metabolites formed after oxidation were 3-hydroxy-benzilate and a propylene glycol derivative of the parent compound.
The metabolic profile of bromopropylate was investigated in urine, feces, and tissue extracts from male and female rats. The study involved single oral administration at a low (0.5 mg/kg bw) and high dose level (100 mg/kg bw), and repeated oral administration at the low dose level. ...In the urine pools, representing 1.7-26.4% of the administered dose, there were 7 distinct metabolite fractions. The metabolite pattern did not significantly differ between the dose levels or dose regimen. However, a pronounced sex difference was observed: the benzilic acid was a minor fraction (10-14%) in males but the major fraction (65-72%) in females. The metabolite pattern in feces did not significantly differ between dose levels, dose regimen and, in contrast to urine, between the sexes. The urinary and fecal metabolic patterns differed qualitatively: there was a non-polar fraction in the feces, corresponding to unchanged bromopropylate, which represented 14-54% of the total fecal radioactivity. The metabolite pattern in liver tissue was not sex-dependent and rather simple with the two major fractions corresponding to bromopropylate and the benzilic acid. The pattern in kidney tissue was also not sex-dependent. It contained only one major fraction accounting for at least 80% of the radioactivity in kidneys and corresponding to the benzilic acid. The benzilic acid accounted for at least 70% and 40% of the radioactivity in male and female lung tissue, respectively. The fat tissue contained unchanged bromopropylate as a major component representing 40% and 80% of the radioactivity for males and females, respectively. Thus, within the tested dose range the metabolism of bromopropylate in the rat was independent of dose level and dose regimen. However, a pronounced sex difference was observed in all groups. The benzilic acid was a minor metabolite in males (approximately 6% of the dose) and the major metabolite in females (approximately 23% of the dose). This parallels the sex difference observed for the route of excretion. The dominant compound in kidney and lung tissue was the benzilic acid, in fat tissue the unchanged bromopropylate, and in liver tissue both were present in substantial amounts.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
副作用
职业性肝毒素 - 第二性肝毒素:在职业环境中的毒性效应潜力是基于人类摄入或动物实验的中毒案例。
Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/
Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/
Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist respirations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Activated charcoal is not effective ... . Do not attempt to neutralize because of exothermic reaction. Cover skin burns with dry, sterile dressings after decontamination ... . /Organic acids and related compounds/
Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Early intubation, at the first sign of upper airway obstruction, may be necessary. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organic acids and related compounds/
One cow received 0.33 mg/kg/day of 14C-labelled bromopropylate in the diet for five days. After a further 13 days without treatment the animal was killed. In the 20 days 94.9% of the administered activity was recovered, 0.96% in the milk, 20.5% in the urine and 73.4% in the feces. No activity was detectable in tissues other than adipose tissue which contained 0.06-0.17 ppm at the time of autopsy
Two male and two female rats were each administered by gavage 1.6 mg 14C-labelled bromopropylate. Expired CO2, urine and feces were collected for the next 120 hours in periods of 24 hours following which blood and other tissues were taken for analysis. Less than 0.2% of activity was found in respired CO2. In males, 90% of activity was found in feces and 6% in urine while in females 55% appeared in feces and 33% in urine. About 75% activity was eliminated in 48 hours but after 120 hours 2.6% (males) and 1.5% (females) of the administered dose remained in tissues, mainly kidneys, liver and fat.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
Bromopropylate在动物体内会迅速有效地被消除。
Bromopropylate is rapidly and efficiently eliminated in animals.
Three groups of three beef calves were each fed diets containing 0, 5 and 50 ppm bromopropylate. Fat biopsies were taken after 2 and 8 weeks of feeding and 1 animal from each group was killed after 4 and 6 weeks. After 10 weeks feeding the remaining animal which had been fed on the 5 ppm diet was killed; the one on 50 ppm was maintained on control diet for a further 2 weeks before it was killed. After 4, 6 and 10 weeks the 5 ppm diet produced respectively levels of 1.5, 1.5 and 2.8 ppm of bromopropylate in the fat. The 50 ppm diet produced fat levels of 7.3 ppm after four, and 8.0 ppm after 6 weeks. After 2 weeks on control diet the concentration of bromopropylate in fat had fallen to 0.3 ppm. Muscle tissue contained low residues of unchanged bromopropylate while liver and kidneys also contained 4,4'-dibromobenzilic acid during the feeding period.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
溴丙酸酯在大鼠体内的吸收、分布和消除进行了评估。[U-14C]苯基溴丙酸酯以单次口服剂量0.5 mg/kg体重(在无效应水平)或100 mg/kg体重(产生一定的药理/毒理效应)给予每组5只雄性和5只雌性大鼠(Sprague-Dawley Crl: CD [SD] BR)。在低剂量水平上,另一组额外接受了14次连续每日剂量0.5 mg/kg体重的非标记化合物(>95%纯度)给药,随后给予单次标记化合物的剂量。在所有三种给药方案下,给药终止后168小时内放射性活性的总回收率达到了90%及以上。大部分剂量通过粪便排出(雄性:85.3-89.3%,雌性:52.5-63.7%)。较少的放射性活性通过尿液排出(雄性:2.3-3%,雌性:21.8-28.7%)。放射性活性的排泄在96小时内基本完成,与剂量水平或预处理无关。没有放射性活性以CO2形式呼出。在低剂量后168小时,组织中溴丙酸酯的浓度较低,最高值在肝脏(雄性或雌性为0.05微克溴丙酸酯当量/克组织)和腹部脂肪(雄性或雌性为0.02或0.03微克溴丙酸酯当量/克组织)。在高剂量下,组织残留模式相似,放射性活性在腹部脂肪中最高(相当于雄性或雌性为3.3或8.7微克/克)。非标记化合物的预处理并没有显著改变168小时后组织残留物,与单次给药的动物相比。得出结论,排泄速率较快,且与剂量水平和预处理无关。消除途径依赖于性别。在给药后168小时观察到低组织残留水平。
The absorption, distribution and elimination of bromopropylate were evaluated in rats. [U-14C]phenyl bromopropylate was given orally at single doses of 0.5 mg/kg bw (at a no-effect level) or 100 mg/kg bw (to produce some pharmacological/toxicological effect) to groups of 5 male and 5 female rats (Sprague-Dawley Crl: CD [SD] BR). At the low dose level an additional group received 14 consecutive daily doses of 0.5 mg/kg bw non-labelled compound (>95% pure) followed by a single dose with radiolabelled compound. Under all three dosing regimens the total recoveries of radioactivity within 168 hr past termination of dosing were 90% and higher. Most of the dose was eliminated in feces (males: 85.3-89.3%, females: 52.5- 63.7%). Lower amounts of radioactivity were excreted in the urine (males: 2.3-3%, females: 21.8-28.7%). Excretion of radioactivity was essentially complete within 96 hr independent of dose level or pretreatment. No radioactivity was expired in CO2. At the low-dose after 168 hr, tissue concentrations were low with highest values in liver (0.05 ug equivalents of bromopropylate/g tissue in male or female) and abdominal fat (0.02 or 0.03 ug equivalents of bromopropylate/g tissue in male or female). At the high dose, the tissue residue pattern was similar, with highest concentration of radioactivity in the abdominal fat (equivalent to 3.3 or 8.7 ug/g in male or female). Pre-treatment with the non-radiolabelled compound did not significantly alter tissue residues at 168 hr post-dose over those animals receiving a single administration. It was concluded that excretion rates were fast, and independent of dose level and pretreatment. The routes of elimination were sex-dependent. The low tissue residue levels were observed at 168 hr after administration.
1.周国泰,化学危险品安全技术全书,化学工业出版社,1997 2.国家环保局有毒化学品管理办公室、北京化工研究院合编,化学品毒性法规环境数据手册,中国环境科学出版社.1992 3.Canadian Centre for Occupational Health and Safety,CHEMINFO Database.1998 4.Canadian Centre for Occupational Health and Safety, RTECS Database, 1989
[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.
Compounds of the formula (I) wherein the substituents are as defined in claim 1, useful as a pesticides, especially fungicides.
式(I)的化合物,其中取代基如权利要求1所定义,作为杀虫剂特别是杀菌剂有用。
[EN] INSECTICIDAL TRIAZINONE DERIVATIVES<br/>[FR] DÉRIVÉS DE TRIAZINONE INSECTICIDES
申请人:SYNGENTA PARTICIPATIONS AG
公开号:WO2013079350A1
公开(公告)日:2013-06-06
Compounds of the formula (I) or (I'), wherein the substituents are as defined in claim 1, are useful as pesticides.
式(I)或(I')的化合物,其中取代基如权利要求1所定义的那样,可用作杀虫剂。
THIENYLPYRIDYLCARBOXAMIDES
申请人:Dunkel Ralf
公开号:US20110105564A1
公开(公告)日:2011-05-05
Novel thienylpyridylcarboxamides of the formula (I)
The present application is also directed to a plurality of processes for preparing these compounds and their use for controlling unwanted microorganisms, and also novel intermediates and their preparation.