Pyrethrins are extensively metabolized, the residues of the parent compound in feces and urine representing only 10%. Six metabolites were identified and two major metabolic pathways were suggested, the first involving oxidation of the double-bond and/or the methyl groups and the second involving hydrolysis of the ester bond. Pyrethrins I are metabolized mainly through oxidative processes, while pyrethrins II are metabolized through a combination of hydrolytic and oxidative processes.
... Within 48 hr of oral admin of (14)C-pyrethrin II to rats, 53% of the (14)C was recovered as exhaled carbon dioxide ... . The ... (14)C recovered from urine ... /was/ 7% ... some of the orally admin material is excreted in feces, at least partially in metabolized form. Three compounds have been isolated from urine & identified by NMR & mass spectra. All three are produced by ... pyrethrin I & II. All three are the result of oxidation of ... the acid & alcoholic moieties leaving the main structure of the molecule intact.
The oral administration of radio-labelled pyrethrin I, or pyrethrin II, to rats produced several urinary metabolites. Each contained a trans-2-carboxyprop-1-enyl side chain resulting from oxidation of the chrysanthemate isobutenyl group or hydrolysis of the pyrethrate methoxy-carbonyl group. Also, the cis-2',4'-pentadienyl side chain of pyrethrin I and pyrethrin II was oxidized at the penta-2,4-dienyl group to give a cis-4',5'-dihydroxypent-2'-enyl group, a 4' conjugate of this diol, or a trans-2',5'-dihydroxypent-3'-enyl group.
The 2-methylpropenyl group of (S)-bioallethrin (A) and the pentadienyl group of pyrethrin II are selectively oxidized by m-chloroperoxybenzoic acid in dichloromethane to yield the 7,8-epoxide (1) from A and a mixture of the 8',9'- and 10',11'-epoxides (7 and 8) from pyrethrin II. These epoxides are hydrated in aqueous acid to the corresponding diols and other hydroxy derivatives produced by opening of the cycloprophyl ring or migration of the adjacent double bond. The epoxy and hydroxy derivatives are identified by two dimensional NMR techniques. Mouse liver enzymes do not detectably hydrate epoxide 1 but quickly hydrate epoxides 7 and 8 without migration of the double bond. HPLC analyses of the microsomal metabolites of pyrethrins I and II identify the 10',11'-diols as major metabolites and the 8',9'-diols as minor products.
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 after potential produce 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 calcium channels and Ca2+, Mg2+-ATPase. (T10, T18, L857)
Pyrethrins 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. (L857, A560)
来源:Toxin and Toxin Target Database (T3DB)
毒理性
致癌性证据
癌症分类：有致癌性的提示性证据，但不足以评估对人类致癌的可能性/除虫菊酯/
Cancer Classification: Suggestive Evidence of Carcinogenicity but Not Sufficient to Assess Human Carcinogenic Potential /Pyrethrins/
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).
来源:Toxin and Toxin Target Database (T3DB)
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).
Pyrethrins are absorbed from the gastrointestinal tract following oral administration. Studies in male rats receiving 3 mg/kg orally resulted in almost complete absorption and metabolism within 100 hours. No pyrethrin was observed in urine, although substantial quantities of metabolites were present. In feces, small quantities of the parent pyrethrin were observed, again accompanied by metabolites.
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
拟除虫菊酯或其代谢物未被已知储存在体内或在乳汁中排出...
The pyrethrins or their metabolites are not known to be stored in the body or to be excreted in the milk...
Following a single oral pyrethrin II dose to rats, 53% of the admin dose appeared as CO2 & 7% appeared in urine. After an equivalent dose of pyrethrin I, 0.3% could be accounted for as CO2 & 46% of the dose was eliminated in urine.
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。
Thieno-pyrimidine compounds having fungicidal activity
申请人：Brewster Kirkland William
公开号：US20070093498A1
公开（公告）日：2007-04-26
The present invention relates to thieno[2,3-d]-pyrimidine compounds having fungicidal activity.
本发明涉及具有杀真菌活性的噻吩[2,3-d]-嘧啶化合物。
Novel insecticides
申请人：Syngenta Participations AG
公开号：EP2540718A1
公开（公告）日：2013-01-02
Compounds of formula I
wherein the substituents are as defined in claim 1, and the agrochemically acceptable salts and all stereoisomers and tautomeric forms of the compounds of formula I can be used as insecticides and can be prepared in a manner known per se.
Molecules having pesticidal utility, and intermediates, compositions, and processes, related thereto
申请人：Dow AgroSciences LLC
公开号：US20180279612A1
公开（公告）日：2018-10-04
This disclosure relates to the field of molecules having pesticidal utility against pests in Phyla Arthropoda, Mollusca, and Nematoda, processes to produce such molecules, intermediates used in such processes, pesticidal compositions containing such molecules, and processes of using such pesticidal compositions against such pests. These pesticidal compositions may be used, for example, as acaricides, insecticides, miticides, molluscicides, and nematicides. This document discloses molecules having the following formula (“Formula One”).
ANTHELMINTIC COMPOUNDS AND COMPOSITIONS AND METHOD OF USING THEREOF
申请人：Meng Charles Q.
公开号：US20140142114A1
公开（公告）日：2014-05-22
The present invention relates to novel anthelmintic compounds of formula (I) below:
wherein
Y and Z are independently a bicyclic carbocyclic or a bicyclic heterocyclic group, or one of Y or Z is a bicyclic carbocyclic or a bicyclic heterocyclic group and the other of Y or Z is alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, heterocyclyl or heteroaryl, and variables X
1
, X
2
, X
3
, X
4
, X
5
, X
6
, X
7
and X
8
are as defined herein. The invention also provides for veterinary compositions comprising the anthelmintic compounds of the invention, and their uses for the treatment and prevention of parasitic infections in animals.
