The primary pathway of metabolism for Dimethenamid-P /in Kfm:WIST rats/ was through glutathione conjugation. The resulting metabolites were products of the breakdown of the glutathione conjugate via 1) the mercapturic acid pathway, 2) to a cysteine conjugate followed by oxidation to the thiolactic acid conjugate and then by further oxidation to the sulfoxide of this conjugate or 3) to the mercaptan which was further modified by S-methylation and succeeding alterations. Additional pathways included the direct modification of the parent compound by demethylation and the oxidation of the methyl groups on the thiophene ring. Dechlorination of the compound and oxidation of the sulfur in the thiophene ring also occurred. Glucuronide and/or sulfate conjugates of metabolites were recovered from the urine, feces and bile.
Five CD rats/sex/group were dosed orally by gavage with 1 or 100 mg/kg of (14C) Dimethenamid-P (radiochemical purity: 98%, specific activity: 50.56 mCi/mmole). The purity of the unlabeled test material was not reported. Urine and feces were collected daily for 3 days. The urine and feces from the individual animals in the respective groups were pooled over the 3 day period in order to analyze for the presence of the plant metabolites, Dimethenamid-P sulfonate, Dimethenamid-P sulfoxide of thioglycolic acid, and Dimethenamid-P thioglycolic acid, in the excretory products. Isolation and purification of these metabolites by thin layer chromatography revealed that Dimethenamid-P sulfonate comprised 0.025 and 0.03% of the urine radiolabel and 0.016 and 0.02% of the fecal radiolabel in the 1 and 100 mg/kg group animals, respectively. The sulfoxide of thioglycolic acid derivative comprised 0.007 and 002% of the radiolabel recovered in the urine of the 1 and 100 mg/kg group animals, respectively. The Dimethenamid-P thioglycolic acid derivative was not recovered in any of the samples.
IDENTIFICATION AND USE: Dimethenamid-P belongs to the chemical family of chloroacetamides and is used as a pre-emergent or early post-emergent herbicide with a broad spectrum of activity against most annual grasses and some important broad leaf weeds. It is taken up through the coleoptiles (grass seedlings) or the roots and emerging shoots (dicotyledonous seedlings) and reduces cell division and plant growth. HUMAN STUDIES: There are no data available. ANIMAL STUDIES: Dimethenamid-P is practically non-irritant to the eyes of rabbits. Three rabbits treated dermally with dimethenamid-P developed slight erythema with no edema and two rabbits developed erythema with no edema. Dimethenamid-P was a skin sensitizer when tested in guinea pigs. The following clinical symptoms of acute dimethenamid-P intoxication in laboratory animals were observed after oral intake: decreased activity, lacrimation, excessive salivation, yellow ano-genital staining, black and/or brown staining on the snout, oral area, buccal area and/or extremities, lethargy, decreased food consumption and decreased fecal volume. After long-term oral treatment, the signs of toxicity observed in rats, mice and dogs were overall similar with the liver as the target organ. The effects observed typically included the increase in one or more serum liver enzymes and changes in cholesterol levels. Increased liver weights were observed in all three species. Histologically, hepatocyte hypertrophy was observed in rats and hepatocyte vacuolation and dilatation of liver sinusoids occurred in dogs. In rat developmental studies, the fetuses in the 150 and 300 mg/kg groups exhibited delayed ossification of the skeleton which was likely related to maternal toxicity. No genotoxic activity was observed in an assay for the induction of unscheduled DNA synthesis in primary cultures of rat hepatocytes exposed for 18-20 hr to dimethenamid-P at concentrations of up to 125 ug/mL. The results of the in vitro as well as the in vivo studies demonstrated, that dimethenamid-P has no mutagenic or clastogenic potential.
/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/
/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). 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 0.9% saline (NS) 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 ... . /Poisons A and B/
来源:Hazardous Substances Data Bank (HSDB)
毒理性
解毒与急救
/SRP:/ 高级治疗：对于无意识、严重肺水肿或严重呼吸困难的病人，考虑进行口咽或鼻咽气管插管以控制气道。使用气囊面罩装置的正压通气技术可能有益。考虑使用药物治疗肺水肿……。对于严重的支气管痉挛，考虑给予β激动剂，如沙丁胺醇……。监测心率和必要时治疗心律失常……。开始静脉输注D5W /SRP: "保持开放"，最小流量/。如果出现低血容量的迹象，使用0.9%的生理盐水（NS）或乳酸林格氏液。对于伴有低血容量迹象的低血压，谨慎给予液体。注意液体过载的迹象……。使用地西泮或劳拉西泮治疗癫痫……。使用丙美卡因氢氯化物协助眼部冲洗……。 /Poisons A and B/
/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
/LABORATORY ANIMALS: Acute Exposure/ Dimethenamid-P (purity: 91.1%) was evaluated for acute eye irritation potential in six male young adult New Zealand White rabbits. Approximately 0.1 mL of undiluted dimethenamid-P was administered to one eye of each rabbit. The test substance was not washed from the eyes. Examination of the eyes was carried out 1, 24, 48 and 72 hr after the application of the test substance. ... All six rabbits exhibited slight conjunctival redness and/or chemosis and moderate to severe conjunctival discharge at 1 hr after exposure. The discharge and chemosis were not observed at 24 hr after treatment. Four animals were free of conjunctival redness by 24 hr and the remaining two animals were free by 48 hr. There were no corneal or iridial effects observed. ...
In the poultry metabolism study, three hens were dosed orally for 4 days with ((14)C)dimethenamid at levels equivalent to 167 ppm (approximately 17,000 x maximum theoretical dietary burden (MTDB) of 0.01 ppm). Total radioactive residues were 8.33 ppm in liver, 0.58 ppm in muscle, 0.29 ppm in fat, 0.30 ppm in egg whites and 0.62 ppm in egg yolks. The metabolism of ((14)C)dimethenamid in hens was extensive, with parent only being identified in fat (34.9% TRR). Other than parent in fat, no one compound appears to account for more than 10% of the TRR in any given tissue. Although only limited identification of (14)C-residues was achieved, the poultry metabolism study was deemed adequate because the dosing level was highly exaggerated compared to the MTDB and the extensive metabolism of dimethenamid resulted in numerous minor metabolites (<10% TRR).
In the ruminant metabolism study, a dairy goat was dosed orally for 4 days with ((14)C)dimethenamid at levels equivalent to 223 ppm (>10,000x the maximum theoretical dietary burden (MTDB) of 0.019 ppm). Total radioactive residues were 16.6 ppm in liver, 9.9 ppm in kidneys, 0.97 ppm in muscle and fat, and 0.98 ppm in milk. ((14)C)Dimethenamid was extensively metabolized and identification of metabolites was limited.
Kfm:WIST rats of both sexes were treated with (14)C Dimethenamid-P technical (specific radioactivity: 157 uCi/mg; radiochemical purity: 99.9%). The specific activity of the dosage preparations was adjusted by supplements of unlabeled Dimethenamid-P technical (purity: 99.8%). ... 6 animals/sex/group were dosed orally by gavage with 10 or 1000 mg/kg, by intravenously with 10 mg/kg of the radiolabeled test material or with 10 mg/kg/day for 14 days with unlabeled test material, followed by a single 10 mg/kg dose of radiolabeled test material. Urine and feces were collected at specified intervals up to 7 days post-dose. In addition, two groups of three animals/sex were dosed orally with 10 mg/kg of the radiolabeled test material. From one group of bile-cannulated rats, bile as well as urine and feces was collected at specified intervals up to 7 days post-dose. Carbon dioxide as well as urine and feces was collected up to 48 hours post-dose from the other group of animals. ... two of the 5 males in the 1000 mg/kg group died. ... For the animals treated with 10 mg/kg orally, 96 to 97% of the administered dose was absorbed (see study in which the bile duct was cannulated). Seventy five to 82% of the dose was recovered in the bile. Eighty to 82% of the administered dose was recovered via excretion within the first 24 hours post-dose. Excretion of the radiolabel in carbon dioxide was quite minimal. Excretion of the radiolabel in the urine was higher for the females than for the males when the animals were dosed at 10 mg/kg ((M) 31 to 35% vs. (F) 47 to 53%). Excretion in the feces was similarly greater for the males ((M) 56 to 62% vs. (F) 37 to 48%). The route or frequency of treatment did not particularly affect this ratio. When the animals were treated with 1000 mg/kg, there was no apparent sexual difference in the excretion profile (urine: 62 to 63%, feces: 26 to 30%). For the animals treated with 10 mg/kg, 55 to 70% of the administered dose was recovered within the first 24 hours. In contrast, only 17 to 19% of the administered dose was recovered within the first 24 hours post-dose from the animals treated with 1000 mg/kg. ...
Kfm:WIST rats of both sexes were treated with (14)C Dimethenamid-P technical (specific radioactivity: 157 uCi/mg; radiochemical purity: 99.9%). The specific activity of the dosage preparations was adjusted by supplements of unlabeled Dimethenamid-P technical (purity: 99.8%). ... 3 rats/sex/group were dosed orally with 10 or 1000 mg/kg or intravenously with 10 mg/kg with the radiolabeled test material. Blood was collected periodically up to 7 days post-dose. ... One of the 3 males in both the 10 and 1000 mg/kg groups died. ... For the animals which were dosed orally, the peak blood levels were achieved only after 24 to 48 hours post-dose and were still quite elevated at 7 days post-dose. In the animals treated intravenously, peak levels were achieved more rapidly and were sustained throughout the 7 day period. ...
[EN] 3-[(HYDRAZONO)METHYL]-N-(TETRAZOL-5-YL)-BENZAMIDE AND 3-[(HYDRAZONO)METHYL]-N-(1,3,4-OXADIAZOL-2-YL)-BENZAMIDE DERIVATIVES AS HERBICIDES<br/>[FR] DÉRIVÉS DE 3-[(HYDRAZONO))MÉTHYL]-N-(TÉTRAZOL-5-YL)-BENZAMIDE ET DE 3-[(HYDRAZONO)MÉTHYL]-N-(1,3,4-OXADIAZOL-2-YL)-BENZAMIDE UTILISÉS EN TANT QU'HERBICIDES
申请人：SYNGENTA CROP PROTECTION AG
公开号：WO2021013969A1
公开（公告）日：2021-01-28
The present invention related to compounds of Formula (I): or an agronomically acceptable salt thereof, wherein Q, R2, R3, R4, R5 and R6 are as described herein. The invention further relates to compositions comprising said compounds, to methods of controlling weeds using said compositions, and to the use of compounds of Formula (I) as a herbicide.
[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。
[EN] HERBICIDALLY ACTIVE HETEROARYL-S?BSTIT?TED CYCLIC DIONES OR DERIVATIVES THEREOF<br/>[FR] DIONES CYCLIQUES SUBSTITUÉES PAR HÉTÉROARYLE À ACTIVITÉ HERBICIDE OU DÉRIVÉS DE CELLES-CI
申请人：SYNGENTA LTD
公开号：WO2011012862A1
公开（公告）日：2011-02-03
The invention relates to a compound of formula (I), which is suitable for use as a herbicide wherein G is hydrogen or an agriculturally acceptable metal, sulfonium, ammonium or latentiating group; Q is a unsubstituted or substituted C3-C8 saturated or mono-unsaturated heterocyclyl containing at least one heteroatom selected from O, N and S, or Q is heteroaryl or substituted heteroaryl; m is 1, 2 or 3; and Het is an optionally substituted monocyclic or bicyclic heteroaromatic ring; and wherein the compound is optionally an agronomically acceptable salt thereof.
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”).
