... Both free and conjugated 3-hydroxy-2,6-dichlorobenzamide were ... isolated as metabolites from apple ... leaves treated directly with 2,6-dichlorobenzamide. Free and conjugated 3-hydroxy-2,6-dichlorobenzamide have been detected chromatographically in wheat seedlings and kale (Brassica oleracea) plants after short-term (1-5 days) root and soil uptake studies with [(14)C]2,6-dichlorobenzamide.
Long-term soil uptake studies (14 weeks) with [(14)C]2,6-dichlorobenzamide showed that the major metabolites in leaves of young apple trees were 3- and 4-hydroxy-2,6-dichlorobenzamide in a ratio of 6:1. Approx 85% of the hydroxylated metabolites were conjugated as glycosides. ... It appears that plants are able to hydroxylate and conjugate ... 2,6-dichlorobenzamide and that hydroxylation at the 3 position ... is favored. A comparison of dichlobenil and 2,6-dichlorobenzamide metabolism after 5 days in root treated bean seedlings showed that 2,6-dichlorobenzamide was hydroxylated and conjugated much slower than dichlobenil.
来源:Hazardous Substances Data Bank (HSDB)
代谢
2,6-二氯苯甲酰胺在大豆中可能被代谢成2,6-二氯苯甲酸。/来自表格/
2,6-Dichlorobenzamide is metabolized to 2,6-dichlorobenzoic acid probably in phaseolus. /From table/
IDENTIFICATION AND USE: 2,6-Dichlorobenzamide (BAM) was formerly used as a pesticide. HUMAN STUDIES: There are no data available. ANIMAL STUDIES: BAM was given to rats (35/sex/dose) for 106 weeks at doses 0, 2.2, 3.6, 6.5, or 19 mg/kg/day in males; 0, 2.8, 4.7, 8.5, or 25 mg/kg/day in females. There was a statistically significant decrease in mean body weight gains in both males and females (10% and 20% less than controls, respectively, at week 52), and slightly increased severity of fat deposition in the livers of females. BAM produced an increased incidence of hepatoma in females. The carcinogenic potential of BAM appears to be less than or equal to that of dichlobenil. In a single dose study in which the group of mice was treated at 250 mg/kg, the mice displayed mild neurotoxic effects (lethargy and ataxia), the group treated at 500 mg/kg were severely affected (becoming comatose), and the groups treated at 1000 mg/kg and higher died in extremis. A mouse micronucleus assay using a single dose of BAM (250 mg/kg) was negative. BAM was negative for inducing repair of DNA damage as measured by unscheduled DNA synthesis (UDS), as determined by net nuclear silver grain count in primary rat hepatocytes, exposed up to cytotoxic doses (1000 ug/mL). BAM was negative for inducing reverse gene mutation in TA strains of Salmonella typhimurium with and without metabolic activation. ECOTOXICITY STUDIES: Short term experiments showed that BAM was moderately toxic to guppies Poecilia reticulata, rainbow trout Salmo gairdneri, daphnids Daphnia magna and the algae Chlorella pyrenoidosa and Scenedesmus pannonicus. In long term studies with daphnids concentrations up to 320 mg/L did not significantly alter survival and reproduction. An embryolarval test with rainbow trout, however, showed a significant reduction of survival and growth as well as a delay of yolk resorption at concentrations equal to or exceeding 18 mg/L. The accumulation of unchanged BAM in leaf tips and margins was reported to be the cause of leaf margin chlorosis.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
致癌性证据
癌症分类：D组 - 不能归类为人类致癌性。
Cancer classification: Group D-Not classifiable as to human carcinogenicity.
/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 as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on 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. /Organic acids and related compounds/
/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). 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 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. 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/
/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. 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. 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 (LR) if signs of hypovolemia are present. 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/
/In foliar and roots/ ... 2,6-dichlorobenzamide is readily absorbed and translocated in xylem with the transpiration stream /and/ ... accumulates ... in foliar tissues. Autoradiograms of apple leaves from seedlings and young trees show that translocated [(14)C]2,6-dichlorobenzamide is distributed throughout the leaf and tends to accumulate at the leaf margins after prolonged periods of root uptake.
Ruthenium-Catalyzed Rearrangement of Aldoximes to Primary Amides in Water
作者：Rocío García-Álvarez、Alba E. Díaz-Álvarez、Javier Borge、Pascale Crochet、Victorio Cadierno
DOI：10.1021/om3006917
日期：2012.9.10
The rearrangement of aldoximes to primaryamides has been studied using the readily available arene-ruthenium(II) complex [RuCl2(η6-C6Me6)P(NMe2)3}] (5 mol %) as catalyst. Reactions proceeded cleanly in pure water at 100 °C without the assistance of any cocatalyst, affording the desired amides in high yields (70–90%) after short reaction times (1–7 h). The process was operative with both aromatic
excellent fungicidalactivities, and the position of the substituents played an important role in fungicidalactivities. Especially, compound 5n, exhibited better fungicidalactivities than the commercial fungicide flutolanil against two tested fungi Valsa mali and Sclerotinia sclerotiorum, with EC50 values of 3.44 and 2.63 mg/L, respectively. And it also displayed good in vivo fungicidalactivity against
Primary amides to amines or nitriles: a dual role by a single catalyst
作者：Hari S. Das、Shyamal Das、Kartick Dey、Bhagat Singh、Rahul K. Haridasan、Arpan Das、Jasimuddin Ahmed、Swadhin K. Mandal
DOI：10.1039/c9cc05856g
日期：——
of various primary amides to amines (25 examples). On simple modification of the reaction conditions such as in the presence of a catalytic amount of secondary amide, the same catalyst can transform the primary amides into intermediate nitrile compounds (16 examples) in excellent yields. This is the first example where such a controlled catalytic transformation of primary amides to amines or nitriles
Cobalt-Catalyzed Allylation of Amides with Styrenes Using DMSO as Both the Solvent and the α-Methylene Source
作者：Xu Zhang、Zhi Zhou、Huiying Xu、Xuefeng Xu、Xiyong Yu、Wei Yi
DOI：10.1021/acs.orglett.9b02462
日期：2019.9.20
An efficient synthesis of privileged allylic amines has been developed via cobalt-catalyzed allylation of amides with styrenes, in which DMSO was used as both the solvent and the α-methylene source. This transformation features high yields, and selectivity for the (E)-isomer of the linear product. Through the experimental and computational investigations, a sequential K2S2O8-mediated oxidative cou
通过将酰胺与苯乙烯进行钴催化的烯丙基化反应，已经开发了一种有效的特权烯丙基胺的合成方法，其中DMSO既用作溶剂，又用作α-亚甲基源。该转化具有高收率和对线性产物的（E）-异构体的选择性。通过实验和计算研究，还推导了顺序的K 2 S 2 O 8介导的氧化偶联/钴辅助的区域选择性烯烃插入/β-H消除/烯烃解离/氢化物转移过程。
An in-depth study of the biotransformation of nitriles into amides and/or acids using Rhodococcus rhodochrous AJ2701
作者：Otto Meth-Cohn、Mei-Xiang Wang
DOI：10.1039/a607977f
日期：——
A variety of aliphatic, aromatic and heterocyclic nitriles have been
readily hydrolysed into the corresponding amides and/or acids under very
mild conditions using Rhodococcus sp. AJ270. The
nitrile hydratase involved in this novel nitrile-hydrolysing
microorganism efficiently hydrates most nitriles tested, irrespective of
the electronic and steric effects of the substituents, to form the
amides. Conversion of amides into acids catalysed by the associated
amidase is rapid and efficient in most cases. Substrates bearing an
adjacent substituent (which may be an ortho
substituent on an aromatic nitrile, an adjacent heteroatom in a
heterocyclic ring or a geminal substituent in an
α,β-unsaturated nitrile) undergo slow hydrolysis of the
amides allowing efficient amide isolation. The scope, limitations and
reaction mechanism of this enzymatic process have been systematically
studied. A molecular size of >7 Å diameter and
the presence of functions capable of metal complexation near to the
nitrile inhibit hydrolysis.
多种脂肪族、芳香族和杂环腈类化合物在非常温和的条件下使用 Rhodococcus sp. AJ270 微生物可以被容易地水解成相应的酰胺和/或酸。这种新型腈水解微生物中涉及的腈水合酶高效地将大多数测试的腈化合物水合形成酰胺，不论取代基的电子和立体效应如何。在大多数情况下，与酰胺酶相关的酸催化反应迅速且高效。具有相邻取代基的底物（可能是芳香腈的邻位取代基，杂环中相邻的杂原子或α,β-不饱和腈中的二重取代基）的酰胺缓慢水解，从而允许高效分离酰胺。该酶促过程的应用范围、局限性和反应机制已被系统研究。分子直径大于7 Å 的大小以及在腈附近存在能够与金属络合的功能会抑制水解。
