Benzobicyclon
(Synonyms: 苯并双环酮) 目录号 : GC38599
Benzobicyclon 是一种促除草剂，抑制植物中 4-羟苯丙酮酸二加氧酶 (4-HPPD) 的活性，导致植物漂白和死亡。
Cas No.:156963-66-5
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
Benzobicyclon is a pro-herbicide, which acts as an inhibitor of 4-hydroxyphenylpyruvate dioxygenase (4-HPPD) in plant, and leads to bleaching and death[1].
[1]. Williams KL, et al. Hydrolytic Activation Kinetics of the Herbicide Benzobicyclon in Simulated Aquatic Systems. J Agric Food Chem. 2016 Jun 22;64(24):4838-44.
| Cas No. | 156963-66-5 | SDF | |
| 别名 | 苯并双环酮 | ||
| Canonical SMILES | O=C1C2CC(C(SC3=CC=CC=C3)=C1C(C4=CC=C(C=C4Cl)S(=O)(C)=O)=O)CC2 | ||
| 分子式 | C22H19ClO4S2 | 分子量 | 446.97 |
| 溶解度 | DMSO : 16.67 mg/mL (37.30 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 | 2.2373 mL | 11.1864 mL | 22.3729 mL |
| 5 mM | 0.4475 mL | 2.2373 mL | 4.4746 mL |
| 10 mM | 0.2237 mL | 1.1186 mL | 2.2373 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。
Aqueous Photolysis of Benzobicyclon Hydrolysate
J Agric Food Chem 2018 Jun 6;66(22):5462-5472.PMID:29754487DOI:10.1021/acs.jafc.8b01012.
Benzobicyclon [3-(2-chloro-4-(methylsulfonyl)benzoyl)-2-phenylthiobicyclo[3.2.1]oct-2-en-4-one] is a pro-herbicide used against resistant weeds in California rice fields. Persistence of its active product, Benzobicyclon hydrolysate, is of concern. As an acidic herbicide, the neutral species photolyzed faster than the more predominant anionic species ( t1/2 = 1 and 320 h, respectively; natural sunlight), from a >10-fold difference in the quantum yield. Dissolved organic matter in natural waters reduced direct photolysis and increased indirect photolysis compared to high-purity water. Light attenuation appears significant in rice field water and can slow photolysis. These results, used in the pesticides in flooded applications model with other experimental properties, indicate that a floodwater hold time of 20 days could be sufficient for dissipation of the majority of initial aqueous Benzobicyclon hydrolysate prior to release. However, soil recalcitrance of both compounds will keep aqueous Benzobicyclon hydrolysate levels constant months after Benzobicyclon application.
Adsorption-desorption behavior of Benzobicyclon hydrolysate in different agricultural soils in China
Ecotoxicol Environ Saf 2020 Oct 1;202:110915.PMID:32800250DOI:10.1016/j.ecoenv.2020.110915.
Benzobicyclon is a systemic herbicide that was officially registered in China in 2018. The environmental behaviors of Benzobicyclon hydrolysate (BH), the main metabolite and active product of Benzobicyclon, remain poorly understood in paddy fields. Here, agricultural soil samples were collected from paddy fields in Jiangxi (Ferralsols), Shandong (Alisols), Hebei (Luvisols), Heilongjiang (Phaeozems), Zhejiang (Anthrosols), Sichuan (Gleysols), Hainan (Plinthosols), and Hubei (Lixisols) across China. The equilibrium oscillation method was used to study the adsorption-desorption behaviors of BH in the eight soils. The relationships between BH adsorption and soil physicochemical properties, environmental factors (temperature and initial solution pH), and other external conditions (addition of humic acid, biochar, and metal ions) were quantified. The adsorption-desorption parameters of BH in all soils were well fitted by the Freundlich model. The adsorption constant of BH varied between 0.066 and 4.728. The BH adsorption capacity decreased in the following order: Phaeozems > Alisols > Ferralsols > Lixisols > Plinthosols > Anthrosols > Luvisols > Gleysols. The Freundlich adsorption and desorption constants of BH were linearly positively correlated with soil clay content (R2 = 0.711 and 0.709; P = 0.009 and 0.009, respectively), organic carbon content (R2 = 0.684 and 0.672; P = 0.011 and 0.013, respectively), and organic matter content (R2 = 0.698 and 0.683; P = 0.010 and 0.011, respectively); however, their linear relationships with soil cation exchange capacity were not significant (R2 = 0.192 and 0.192; P = 0.278 and 0.278, respectively). The adsorption and desorption constants of BH had negative, albeit not significant, correlations with soil pH (R2 = 0.104 and 0.100; P = 0.437 and 0.445, respectively). The adsorption of BH by soil occurred spontaneously and was mainly based on physical adsorption. Either low or high temperature reduced the ability of the soil to adsorb BH. The addition of humic acid to the soil increased BH adsorption, while the addition of biochar increased the solution pH, resulting in decreased BH adsorption. Cation type and ionic strength also had strong effects on BH adsorption. With the exception of Phaeozems, BH exhibited intermediate or high mobility in the agricultural soils and thus poses risks to surface water and groundwater.
Presence of the HPPD Inhibitor Sensitive 1 Gene and ALSS653N Mutation in Weedy Oryza sativa Sensitive to Benzobicyclon
Plants (Basel) 2020 Nov 14;9(11):1576.PMID:33202609DOI:10.3390/plants9111576.
Benzobicyclon has shown varying results in controlling weedy rice, including those with imidazolinone (IMI) resistance. Tolerance to Benzobicyclon in cultivated japonica rice, but not indica or aus-like cultivars, is conferred by a fully functional HPPD Inhibitor Sensitive 1 (HIS1) gene. Herein, a diagnostic Kompetitive Allele Specific PCR (KASP) assay was developed to predict the HIS1 genotype of weedy rice plants from 37 accessions and correlated to their response to Benzobicyclon in the field. Two-thirds of the 693 weedy rice plants screened were tolerant to Benzobicyclon (371 g ai ha-1, SC formulation) at 30 days after treatment (DAT). Thirty-four percent of plants were homozygous for the HIS1 allele and 98% of these plants exhibited field tolerance. However, the his1 genotype did not always correlate with field data. Only 52% of his1 plants were considered sensitive, indicating that the single nucleotide polymorphisms (SNPs) chosen in the KASP assay are not a reliable tool in predicting his1 homozygous plants. In an additional experiment, 86% of the 344 plants with at least one copy of the ALSS653N trait harbored a HIS1 allele, suggesting fields infested with IMI herbicide-resistant weedy rice are unlikely to be controlled with Benzobicyclon.
Hydrolytic Activation Kinetics of the Herbicide Benzobicyclon in Simulated Aquatic Systems
J Agric Food Chem 2016 Jun 22;64(24):4838-44.PMID:27248841DOI:10.1021/acs.jafc.6b00603.
Herbicide resistance is a growing concern for weeds in California rice fields. Benzobicyclon (BZB; 3-(2-chloro-4-(methylsulfonyl)benzoyl)-2-phenylthiobicyclo[3.2.1]oct-2-en-4-one) has proven successful against resistant rice field weeds in Asia. A pro-herbicide, BZB forms the active agent, Benzobicyclon hydrolysate (BH), in water; however, the transformation kinetics are not understood for aquatic systems, particularly flooded California rice fields. A quantitative experiment was performed to assess the primary mechanism and kinetics of BZB hydrolysis to BH. Complete conversion to BH was observed for all treatments. Basic conditions (pH 9) enhanced the reaction, with half-lives ranging from 5 to 28 h. Dissolved organic carbon (DOC) hindered transformation, which is consistent with other base-catalyzed hydrolysis reactions. BH was relatively hydrolytically stable, with 18% maximum loss after 5 days. Results indicate BZB is an efficient pro-herbicide under aqueous conditions such as those of a California rice field, although application may be best suited for fields with recirculating tailwater systems.
Residue Analysis of Benzobicyclon in Soil and Sediment Samples by Ultra High-Performance Liquid Chromatography-Tandem Mass Spectrometry
J AOAC Int 2016 Nov 1;99(6):1628-1635.PMID:27653995DOI:10.5740/jaoacint.16-0159.
A reliable and rapid method was developed to determine Benzobicyclon residue in different soil and sediment samples. After extraction via a modified quick, easy, cheap, effective, rugged, and safe method, samples were purified by SPE cleanup with HLB cartridges. Quantitative determination was performed by ultra-HPLC (UPLC)-tandem MS (MS/MS) in electrospray positive ionization and multiple reaction monitoring modes. When samples were fortified at concentrations of 5, 50, and 500 µg/L, recoveries of 80.2 to 114.5% were obtained, with the repeatability (intraday RSDr) and reproducibility (interday RSDR) <14.1 and <21.4%, respectively. The instrumental LODs and LOQs for matrix-matched standards and the method LOQs for sample test were 0.19-1.34 μg/L, 0.64-4.48 μg/L, and 0.32-2.24 μg/kg, respectively. The linear range was 5-1000 μg/L (R2 > 0.99). The established UPLC-MS/MS method was applied in the detection of Benzobicyclon in real soil samples, which were collected during the supervised field trial. Results showed that the maximum concentration of Benzobicyclon in the soil was 4.87 mg/kg and its degradation half-life (t0.5) was 6.7 days. Generally, the proposed method could be an effective tool for controlling and monitoring the risks posed by Benzobicyclon to human health and environmental safety.