Dicamba is a white solid dissolved in a liquid carrier. The carrier is water emulsifiable. The primary hazard is the threat to the environment. Immediate steps should be taken to limit its spread to the environment. Since it is a liquid it can easily penetrate the soil and contaminate groundwater and nearby streams. It can cause illness by inhalation, skin absorption and/or ingestion. It is used as a herbicide.
The oral absorption of dicamba has been quantified in urinary excretion studies ... A mixture of (14)C-labeled dicamba (98% pure) and technical dicamba /was administered/ to Charles River CD rats by a single gavage dose in peanut oil (0.1 and 0.9 g/kg), via diet (10-20,000 ppm) for 24 hr, or by a single sc injection in peanut oil (0.1 g/kg). Following gavage or subcutaneous exposure, approximately 93% and 96% of the administered (14)C-dicamba, respectively, was excreted unmetabolized in the urine within 24 hr of dosing. With dietary exposure, urinary and fecal excretion approached 96% and 4% of the rate of intake. Dicamba was excreted unchanged in the urine (20% was conjugated with glucuronic acid). Similarly, following a single oral dose of 100 mg/kg of (14)Cdicamba (99% pure) in rats, mice, rabbits, and dogs, 67-83% of the radioactivity was eliminated in the urine as parent compound within 48 hr. About 1% of the administered dose was metabolized to 3,6-dichlorosalicylic acid (3,6-DCSA or 3,6-dichloro-2-hydroxybenzoic acid) and another 1% to an unidentified metabolite.
While there are no studies available to evaluate the estimated dermal permeability coefficient for dicamba, the estimated first-order dermal absorption rate in humans can be compared to the first order dermal absorption rate determined in rats ... In this study, both dicamba and 3,5-dichloro isomer were dissolved in acetone and applied to shaved skin (6 sq cm, 0.8, or 4.1 mg/sq cm), and covered with plastic film. The highest blood concentrations of dicamba and isomer were found at 1 and 9 hr, respectively ... The disappearance of both chemicals from the blood followed first order kinetics, and findings for combined exposure were similar to that for the individual chemicals. The half-times in blood were 0.4 hr for dicamba and 3.6 hr for the isomer, suggesting that dermal absorption was the rate limiting step in urinary elimination of the isomer. As estimated from urinary excretion, 14.1 and 7.5% of the applied dermal doses of dicamba and isomer were absorbed. The absorption rates through the skin were 0.0029/ hr for dicamba and 0.0012/ hr for the isomer. /Dicamba, 3,5-dichloro isomer/
... There are two major plant metabolites 3,6-dichloro-5-hydroxybenzoic acid (5-OH dicamba) and 3,6-dichlorosalicylic acid (DCSA), which are structurally similar to the parent compound ...
Metabolism of dicamba by wheat (Var gaines) and bluegrass (Var newport) plants yielded 3 metabolites. GLC, infrared and mass spectrometry were used to identify the major (90%) metabolite as 5-hydroxy-2-methoxy-3,6-dichlorobenzoic acid. After hydrolysis by beta glucosidase, one of minor (5%) residues was ... dicamba. Second minor (5%) metabolite was ... 3,6-dichlorobenzoic acid. The data indicated that 5-hydroxy-dicamba and 3,6-dichlorogentisic acid were major metbolites in young barley plants treated with dicamba.
IDENTIFICATION AND USE: Dicamba is a crystalline solid, white (reference grade) or brown (technical grade). It is a growth regulating herbicide. It controls broadleaf weeds in asparagus, corn (field, silage, popcorn), grass seed crops, grain sorghum, noncropland, pastures, rangeland, reduced-tillage, fallow, small grains not underseeded to legumes, sugarcane, turf, between cropping; brush and vines in pastures, industrial areas, noncropland, rangeland; perennial broadleaf weeds with spot treatments and ropewick applications. HUMAN STUDIES: Dicamba is moderately toxic by ingestion and slightly toxic by inhalation or dermal exposure. Symptoms of poisoning with dicamba include loss of appetite (anorexia), vomiting, muscle weakness, slowed heart rate, shortness of breath, central nervous system effects (victim may become excited or depressed), benzoic acid in the urine, incontinence, cyanosis (bluing of the skin and gums), and exhaustion following repeated muscle spasms. In addition to these symptoms, inhalation can cause irritation of the linings of the nasal passages and the lungs, and loss of voice. Most individuals who have survived severe poisoning from dicamba have recovered within 2 to 3 days with no permanent effects. Dicamba is capable of inducing DNA damage since it significantly increases the unwinding rate for liver DNA in vivo and also induces unscheduled DNA synthesis in human peripheral blood lymphocytes in vitro in the presence of exogenous metabolic activation. Furthermore, dicamba causes a very slight increase in sister chromatid exchange frequency in human peripheral blood lymphocytes in vitro. ANIMAL STUDIES: In rabbits, dose-related dermal irritation was observed. Desquamation was seen predominantly in the 1000 mg/kg/day group while moderate erythema, moderate edema and atonia were observed exclusively in the 1000 mg/kg/day group. Technical dicamba was fed in diet to rats (60/sex/group) at 0, 50, 250 or 2500 ppm in the diet for 115 to 118 weeks. Brain ventricular dilatation associated with pituitary anterior adenomas were observed in females at >/= 250 ppm. Adrenal enlargement was increased at >/= 250 ppm in both sexes. Increased macroscopic lesions in liver at >/= 250 ppm (males) and lesions in lymph nodes at 2500 ppm (males) were observed. There were increased malignant lymphomas in females at >/= 250 ppm, increased parafollicular cell carcinoma, and adenoma, as well as increased follicular adenoma and carcinomas in treated males, primarily at 2500 ppm, but could be extended down to the lower doses. Chronic treatment of adult and newborn rats with less than 0.04xLD50 of dicamba caused disorder of oxidative phosphorylation and focal necrosis in the heart. Similar changes were observed in rat embryos of dams exposed to the pesticide. In a rat developmental study, no treatment-related fetotoxicity or developmental effects were observed at any dose level based on assessments of numbers of pregnancies, implantation and resorption sites, and viable and dead fetuses, as well as litter weights and external, skeletal and visceral fetal examinations. Dicamba was negative in the Ames test with Salmonella typhimurium TA98, TA100, TA1535, TA1537 and TA102 with or without activation. ECOTOXICITY STUDIES: In fish, dicamba exposure could result in histological lesions, plasma vitellogenin increases, changes in sex hormone levels, and alterations of hormone-related gene expression. Dicamba induced primary DNA breaks in amphibians. Dicamba significantly increased lady beetle mortality and reduced their body weight. Plants exposed to sublethal levels of dicamba may produce fewer floral resources and be less frequently visited by pollinators.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
致癌性证据
癌症分类：D组 不可归类为人类致癌性
Cancer Classification: Group D Not Classifiable as to Human Carcinogenicity
来源:Hazardous Substances Data Bank (HSDB)
毒理性
致癌物分类
对人类无致癌性（未列入国际癌症研究机构IARC清单）。
No indication of carcinogenicity to humans (not listed by IARC).
In oral, dermal, and inhaled routes of exposure, dicamba has a low acute toxicity. Dicamba may have irritating or corrosive effects on the skin and eyes. The EPA has identified dicamba as a developmental toxin in the Toxics Release Inventory. (L2156)
来源:Toxin and Toxin Target Database (T3DB)
毒理性
暴露途径
这种物质可以通过摄入被身体吸收。
The substance can be absorbed into the body by ingestion.
来源:ILO-WHO International Chemical Safety Cards (ICSCs)
Toxicokinetics and recovery studies of dicamba dimethyl amine salt (DDAS) were conducted to obtain more information about its toxicity and tissue retention in farm animals. The minimum oral toxic dose level of DDAS was determined as 1400 mg/kg body weight. In the toxicokinetic study, blood DDAS concentration of 55.6 +/- 0.59 ug/mL (mean +/- standard error) was detected at 0.08 hr, which peaked to 102.3 +/- 5.03 ug/mL at 0.25 hr, and declined to a minimum of 4.1 +/- 0.06 ug/mL at 36 hr. In recovery studies, DDAS concentration in urine began to increase significantly (P < 0.05) from 12 hr, peaked at 24 hr and declined from 48 hr onwards. Maximum excretion through feces was at 24 hr and was complete by 144 hr. The residual level in tissues decreased significantly (P < 0.05) on day 7 as compared to day 4. In histopathological studies, cellular alterations in lungs, liver, kidney, adrenal gland and spleen were found. DDAS persists in the body for a shorter period and its major excretory route is through urine. DDAS has lower affinity to accumulate in tissues, and intensity of cellular alterations is not severe after single-dose oral administration. /Dicamba dimethyl amine salt/
In a plasma pharmacokinetic study, five groups of 4 male and 4 female Wistar rats received diets containing the equivalent of 50, 100, 200, 400, or 800 mg/kg dicamba/day for 90 days (Lot No. 52103810, 87.2% a.i.) . On study days 29, 63, and 91, dietary supplementation of dicamba was stopped and rats in each group received an equivalent gavage dose of (14)C-dicamba (Lot No. 787-0102, >99% a.i., universally labeled in the phenyl group). Blood samples were drawn 0.5, 1, 2, 4, 6, 8, 12, 24, and 48 hr after treatment and the plasma radioactivity determined. Absorption of the radiolabeled test material was rapid, with peak plasma concentrations found within 2 hr of treatment. Absorption was not saturated, even at the highest dose, as indicated by increasing plasma concentrations with dose. However, the increase in plasma concentration was disproportionate from dose as shown by the >/= 2-fold increase in AUC from one dose group to the next at doses > 100 mg/kg. Elimination of radiolabel from the plasma was tri-phasic, with the terminal-phase consistent between doses. However, the initial elimination phase increased with dose, particularly in the 400 and 800 mg/kg dose groups and is consistent with excretion saturation. No significant treatment-related differences between the sexes or time of radiolabel administration were found.
In a pharmacokinetic study, two groups of 3 male Wistar rats were given a single 200 mg/kg gavage dose of (14)C-dicamba (Lot No. 787-0102, > 99% a.i., universally labeled in the phenyl group). One group of rats was pretreated with a 150 mg/kg IP dose of probenecid , a known competitive inhibitor of renal anion transport, 30 min prior to dicamba dosing. Blood samples were drawn 0.5, 1, 2, 4, 6, 8, 12, 24, and 48 hr after gavage treatment and the plasma radioactivity determined. The time to peak plasma concentration in rats treated with (14)C-dicamba occurred within 0.5 hr while peak plasma concentration was reached at 1.0 hr in the probenecid/dicamba rats. However, pretreatment with probenecid increased plasma AUC by a factor of 1.54. Although the terminal phase of elimination remained relatively the same, the initial and intermediate elimination phases were increased by a factor of two. These data suggest that both dicamba and probenecid act as inhibitors of renal anion transport.
Dicamba is rapidly and extensively absorbed following oral exposure and rapidly excreted predominantly as unmetabolized compound in the urine. Oral studies in rats indicate that there are no significant pharmacokinetic differences in the free acid and amine salt forms of dicamba. Dermal absorption of dicamba has been demonstrated but is less well studied than oral absorption.
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
Degradation of benomyl, picloram, and dicamba in a conical apparatus by zero-valent iron powder
摘要：
Reduction of some pesticides (benomyl, picloram, and dicamba) was studied in an aerobic batch conical pilot system to investigate the disappearance of these pesticides on contact with iron powder (20 g/l, 325-mesh). Aqueous buffered solutions of the compounds were added to the system followed by zero-valent iron powder (ZVIP), and the decline in the pesticide concentrations was monitored over time. HPLC analyses show a complete disappearance of picloram (1.20 mg/l) after 20 min of reaction. Benomyl (1.00 mg/l) and dicamba (1.25 mg/l) disappear after 25 and 40 min, respectively. The t(50) values ranged From 3 to 5.5 min, and were about slightly less than the t(1/2) values reported when the log of the relative HPLC peak area was plotted versus time, where the relative peak area was calculated by dividing the measured peak area by the initial peak area. Pathways for the degradation of the studied pesticides by ZVIP are proposed. (C) 2001 Elsevier Science Ltd. All rights reserved.
[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] 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.
HERBICIDAL AND FUNGICIDAL 5-OXY-SUBSTITUTED 3-PHENYLISOXAZOLINE-5-CARBOXAMIDES AND 5-OXY-SUBSTITUTED 3-PHENYLISOXAZOLINE-5-THIOAMIDES
申请人：BAYER CROPSCIENCE AG
公开号：US20150245616A1
公开（公告）日：2015-09-03
Herbicidally and fungicidally active 5-oxy-substituted 3-phenylisoxazoline-5-carboxamides and 5-oxy-substituted 3-phenylisoxazoline-5-thioamides of the formula (I) are described.
In this formula (I), X, X
2
to X
6
, R
1
to R
4
are radicals such as hydrogen, halogen and organic radicals such as substituted alkyl. A is a bond or a divalent unit. Y is a chalcogen.
[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.
