Captan
(Synonyms: 克菌丹) 目录号 : GC47035
A fungicide
Cas No.:133-06-2
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Captan is a trichloromethyl sulfenyl fungicide that degrades into thiophosgene, a highly reactive compound that reacts with thiol and non-thiol proteins, in cells.1 It reduces radial growth of and starch depletion by A. fumigatus on the leaf surface of A. tenuis when used at a concentration of 50 μg/ml.2 Captan (50-1,000 mg/kg) increases the number of micronuclei and chromosomal aberrations in polychromatic erythrocytes in bone marrow in mice.3 It also induces chromosomal aberrations in spermatocytes and sperm head abnormalities in mice. Captan reduces survival of adult male and female alfalfa leafcutting bees (M. rotunda) when applied topically or administered in the diet at concentrations of 150-684 and 24.45-48.9 g/L, respectively.4
1.Long, J.W., and Siegel, M.R.Mechanism of action and fate of the fungicide chlorothalonil (2,4,5,6-tetrachloroisophthalonitrile) in biological systems. 2. In vitro reactionsChem. Biol. Interact.10(6)383-394(1975) 2.Kithubutheen, A.J., and Pugh, G.J.Effects of fungicides on Aspergillus fumigatusAntonie Van Leeuwenhoek45(2)303-312(1979) 3.Feng, J.Y., and Lin, B.Y.Cytogenetic effects of an agricultural antibiotic, captan, on mouse bone marrow and testicular cellsEnviron. Res.43(2)359-363(1987) 4.Huntzinger, C.I., James, R.R., Bosch, J., et al.Fungicide tests on adult alfalfa leafcutting bees (Hymenoptera: Megachilidae)J. Econ. Entomol.101(4)1088-1094(2008)
| Cas No. | 133-06-2 | SDF | |
| 别名 | 克菌丹 | ||
| Canonical SMILES | O=C1N(SC(Cl)(Cl)Cl)C(C2CC=CCC21)=O | ||
| 分子式 | C9H8Cl3NO2S | 分子量 | 300.6 |
| 溶解度 | DMSO : 50 mg/mL (166.34 mM; Need ultrasonic) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.3267 mL | 16.6334 mL | 33.2668 mL |
| 5 mM | 0.6653 mL | 3.3267 mL | 6.6534 mL |
| 10 mM | 0.3327 mL | 1.6633 mL | 3.3267 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Captan (Pesticides)
Food Saf (Tokyo) 2017 Jun 30;5(2):61-66.PMID:32231930DOI:10.14252/foodsafetyfscj.2017003s.
Food Safety Commission of Japan (FSCJ) conducted a risk assessment of Captan (CAS No. 133-06-2), a phthalimide fungicide, based on results from various studies. Major adverse effects of Captan were observed in suppressed body weight, and also in duodenal mucosal hyperplasia in mice. No adverse effect on fertility was detected. Increases in incidence of duodenal adenoma and adenocarcinoma were identified in mice. Negative results were however obtained from a gene mutation assay of the target in transgenic mice. No genotoxicity relevant to human health of Captan was recognized in spite of the positive results in vitro. Therefore, a genotoxic mechanism was unlikely involved in the tumor development, and it enabled us to establish a threshold in the assessment. In developmental toxicity studies, Captan, at the doses causing maternal toxicity, increased external alterations as well as skeletal and soft tissue alterations in the fetus of rabbits and hamsters. No captan-induced teratogenicity was detected in rats. Captan (parent compound only) was identified as the residue definition for dietary risk assessment in agricultural and livestock products. The lowest no-observed-adverse-effect level (NOAEL) obtained from all the studies was 10 mg/kg bw/day. FSCJ specified an acceptable daily intake (ADI) of 0.1 mg/kg bw/day by applying a safety factor of 100 to the NOAEL. The lowest NOAEL for potential adverse effects of a single oral administration of Captan was 30 mg/kg bw/day in a developmental toxicity study in rabbits. FSCJ specified an acute reference dose (ARfD) of 0.3 mg/kg bw, for women who are or may be pregnant, by applying a safety factor of 100 to the NOAEL. In addition, FSCJ specified an ARfD of 3 mg/kg bw, for general population, by applying a safety factor of 100 to the no-observed-effect level (NOEL) of 300 mg/kg bw obtained from a general pharmacology study in mice.
Captan exposure disrupts ovarian homeostasis and affects oocytes quality via mitochondrial dysfunction induced apoptosis
Chemosphere 2022 Jan;286(Pt 1):131625.PMID:34303901DOI:10.1016/j.chemosphere.2021.131625.
Captan is a non-systematic fungicide widely used in agricultural production, and its residues have been found in the environment and daily diet. Previous studies confirmed that Captan exerts several toxic effects on tissues, but its effect on the mammalian female reproductive system is unclear. In current study, we reported that Captan affected mouse ovarian homeostasis and disrupted female hormone receptor expression, leading to impaired follicular development. Ovarian follicles from the Captan exposure group showed an increased level of inflammation, endoplasmic reticulum stress and apoptosis. In addition, Captan exposure disrupted oocyte development. Transcriptomic analysis indicated that Captan changed multiple genes expression in oocytes, including autophagy and apoptosis. Further molecular testing showed that Captan induced oxidative stress and mitochondrial dysfunction, as indicated by the increased level of reactive oxygen species, disrupted mitochondrial structure and distribution, and depolarized membrane potential. Furthermore, Captan triggered DNA damage, autophagy and early apoptosis, as shown by the enhanced levels of γ-H2AX, LC3, and Annexin-V and increased expression of related genes. Taken together, these results indicated that Captan exposure impairs ovarian homeostasis and subsequently affects oocyte development.
Genetic toxicology of folpet and Captan
Crit Rev Toxicol 2010 Jul;40(6):546-74.PMID:20569196DOI:10.3109/10408444.2010.481663.
Folpet and Captan are fungicides whose genotoxicity depends on their chemical reaction with thiols. Multiple mutagenicity tests have been conducted on these compounds due to their positive activity in vitro and their association with gastrointestinal tumors in mice. A review of the collective data shows that these compounds have in vitro mutagenic activity but are not genotoxic in vivo. This dichotomy is primarily due to the rapid degradation of folpet and Captan in the presence of thiol-rich matrices typically found in vivo. Genotoxicity has not been found in the duodenum, the mouse tumor target tissue. It is concluded that folpet like Captan presents an unlikely risk of genotoxic effects in humans.
An adverse outcome pathway for small intestinal tumors in mice involving chronic cytotoxicity and regenerative hyperplasia: a case study with hexavalent chromium, Captan, and folpet
Crit Rev Toxicol 2020 Sep;50(8):685-706.PMID:33146058DOI:10.1080/10408444.2020.1823934.
Small intestinal (SI) tumors are relatively uncommon outcomes in rodent cancer bioassays, and limited information regarding chemical-induced SI tumorigenesis has been reported in the published literature. Herein, we propose a cytotoxicity-mediated adverse outcome pathway (AOP) for SI tumors by leveraging extensive target species- and site-specific molecular, cellular, and histological mode of action (MOA) research for three reference chemicals, the fungicides Captan and folpet and the transition metal hexavalent chromium (Cr(VI)). The gut barrier functions through highly efficient homeostatic regulation of SI epithelial cell sloughing, regenerative proliferation, and repair, which involves the replacement of up to 1011 cells per day. This dynamic turnover in the SI provides a unique local environment for a cytotoxicity mediated AOP/MOA. Upon entering the duodenum, cytotoxicity to the villous epithelium is the molecular initiating event, as indicated by crypt elongation, villous atrophy/blunting, and other morphologic changes. Over time, the regenerative capacity of the gut epithelium to compensate declines as epithelial loss accelerates, especially at higher exposures. The first key event (KE), sustained regenerative crypt proliferation/hyperplasia, requires sufficient durations, likely exceeding 6 or 12 months, due to extensive repair capacity, to create more opportunities for the second KE, spontaneous mutation/transformation, ultimately leading to proximal SI tumors. Per OECD guidance, biological plausibility, essentiality, and empirical support were assessed using modified Bradford Hill considerations. The weight-of-evidence also included a lack of induced mutations in the duodenum after up to 90 days of Cr(VI) or Captan exposure. The extensive evidence for this AOP, along with the knowledge that human exposures are orders of magnitude below those associated with KEs in this AOP, supports its use for regulatory applications, including hazard identification and risk assessment.
Detection of Captan residues in apple juice using fluorescence spectroscopy combined with a genetic algorithm and support vector machines
Appl Opt 2022 Apr 20;61(12):3455-3462.PMID:35471442DOI:10.1364/AO.451831.
The Captan residues in apple juice were detected by fluorescence spectrometry, and the content level of Captan was predicted based on a genetic algorithm and support vector machines (GA-SVMs). According to the Captan concentration in apple juice, the experimental samples were divided into four levels, including no excess, slight excess, moderate excess, and severe excess. A GA was used to select the characteristic wavelength and optimize SVM parameters, and SVM was applied to train the classification model. 50 characteristic wavelength points were selected from the original fluorescence spectra, which contained 401 wavelength points, and the classification accuracy of the training set and test set is 99.02% and 100%, respectively, which is higher than the traditional PLS method. The results show that a GA can effectively select the feature wavelengths, and an SVM model can accurately predict the content level of Captan residues. A fast and non-destructive analysis method, combined with a GA and SVM based on fluorescence spectroscopy, was realized.