Haloxyfop
(Synonyms: 吡氟氯禾灵) 目录号 : GC64300
Haloxyfop 是一种芳氯氧苯氧丙酸除草剂 (herbicide)，广泛应用于阔叶作物的野草。Haloxyfop 对玉米幼苗叶绿体中乙酰辅酶 A 羧化酶 (EC 6.4.1.2) 的抑制作的 IC50 为 0.5 μM，而对豌豆中该酶无影响。
Cas No.:69806-34-4
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
Haloxyfop is an aryloxyphenoxypropionic acid herbicide and is widely used in grass weeds in broad-leaf crops[2]. Haloxyfop inhibits the acetyl coenzyme A carboxylase (EC 6.4.1.2) from corn seedling chloroplasts with an IC50 of 0.5 μM, but has no effect on this enzyme in pea[2].
[1]. Urairat Koesukwiwat, et al. Method Development and Validation for Total Haloxyfop Analysis in Infant Formulas and Related Ingredient Matrices Using Liquid Chromatography-Tandem Mass Spectrometry. Anal Bioanal Chem
[2]. J D Burton, et al. Inhibition of Plant Acetyl-Coenzyme A Carboxylase by the Herbicides Sethoxydim and Haloxyfop. Biochem Biophys Res Commun
| Cas No. | 69806-34-4 | SDF | Download SDF |
| 别名 | 吡氟氯禾灵 | ||
| 分子式 | C15H11ClF3NO4 | 分子量 | 361.7 |
| 溶解度 | DMSO : 100 mg/mL (276.47 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 | 2.7647 mL | 13.8236 mL | 27.6472 mL |
| 5 mM | 0.5529 mL | 2.7647 mL | 5.5294 mL |
| 10 mM | 0.2765 mL | 1.3824 mL | 2.7647 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。
Haloxyfop determination by gas chromatography/tandem mass spectrometry in eggs
Rapid Commun Mass Spectrom 2020 Oct 15;34(19):e8895.PMID:32662916DOI:10.1002/rcm.8895.
Rationale: Haloxyfop is a pre/post-emergence herbicide with known organ toxicities and teratogenic effects in mammals. The European Union Commission on Food Safety has an established maximum residue limit of 10 μg/kg in all agricultural products including eggs. A sensitive highly specific method would be of value in determination of Haloxyfop residues in foodstuffs such as eggs. Methods: The Michigan State University Veterinary Diagnostic Lab (MSU VDL) developed a method for the extraction of Haloxyfop from eggs based on popular QuEChERS (quick, easy, cheap, effective, rugged, and safe) methodologies, essentially providing acetonitrile extracts following treatment with high ionic strength additives. Extracts derivatized with trimethylsilyl (TMS) groups were examined by gas chromatography/tandem mass spectrometry using developed multiple reaction monitoring (MRM) methodology. Results: The MSU VDL received eggs from chickens exposed to 760 μg/kg Haloxyfop in flaxseed. Haloxyfop-TMS m/z 374→73 MRM setting enabled quantitation across the 1-50 ppb range in comparison with an ibuprofen MRM transition as internal standard. Conclusions: The determined limit of quantitation was 2.5 ng/g, and the method successfully identified Haloxyfop residues in five of six batches of the chicken eggs, with nonzero values ranging from 2.7 to 14.5 ng/g. These values were consistent with flaxseed incorporation into the diet at 4-7% and known excretion into eggs at 2-3% of daily Haloxyfop exposure, and establish the utility of the method in identifying regulatory noncompliance and adulteration of food sources.
Molecular characteristics of the first case of haloxyfop-resistant Poa annua
Sci Rep 2020 Mar 6;10(1):4231.PMID:32144361DOI:10.1038/s41598-020-61104-0.
Haloxyfop is one of two acetyl-coenzyme A carboxylase (ACCase) inhibitors that is recommended for controlling Poa annua. We have characterised a population of P. annua that had developed resistance to Haloxyfop. This resistant population was found to be almost 20 times less sensitive to Haloxyfop than a susceptible population based on percentage survival of individuals in two dose-response experiments. However, the haloxyfop-resistant population was still susceptible to clethodim. Pre-treatment of resistant individuals with a cytochrome P450 inhibitor, malathion, did not change the sensitivity level of the resistant plants to Haloxyfop, suggesting that a non-target site mechanism of resistance involving enhanced metabolism, was not responsible for this resistance in P. annua. Gene sequencing showed that a target site mutation at position 2041, which replaced isoleucine with threonine in the carboxyltransferase (CT) domain of the ACCase enzyme, was associated with resistance to Haloxyfop in the resistant population. An evaluation of the 3-D structure of the CT domain suggested that, unlike Asn-2041, which is the most common mutation at this position reported to date, Thr-2041 does not change the conformational structure of the CT domain. This is the first study investigating the molecular mechanism involved with Haloxyfop resistance in P. annua.
Influence of the herbicide haloxyfop-R-methyl on bacterial diversity in rhizosphere soil of Spartina alterniflora
Ecotoxicol Environ Saf 2020 May;194:110366.PMID:32126413DOI:10.1016/j.ecoenv.2020.110366.
Haloxyfop-R-methyl (Haloxyfop) can efficiently control Spartina alterniflora in coastal ecosystems, but its effect on soil microbial communities is not known. In the present study, the impact of the Haloxyfop on rhizosphere soil bacterial communities of S. alterniflora over the dissipation process of the herbicide has been studied in a coastal wetland. The response of the bacterial community in the rhizoplane (iron plaque) of S. alterniflora subjected to Haloxyfop treatment was also investigated. Results showed that the persistence of Haloxyfop in the rhizosphere soil followed an exponential decay with a half-life of 2.6-4.9 days, and almost all of the Haloxyfop dissipated on Day 30. The diversity of rhizosphere soil bacteria was decreased at the early stages (Days 1, 3 & 7) and recovered at late stages (Days 15 & 30) of the Haloxyfop treatment. Application of Haloxyfop treatment increased the relative abundance of the genera Pseudomonas, Acinetobacter, Pontibacter, Shewanella and Aeromonas. Strains isolated from these genera can degrade herbicides efficiently, which possibly played a role in the degradation of Haloxyfop. The rhizoplane bacterial diversity was reduced on Day 15 while being vastly enhanced on Day 30. Soil variables, including the electric conductivity, redox potential, and soil moisture, along with the soil Haloxyfop residue, jointly shape the bacterial community in rhizosphere soil.
Haloxyfop Inhibition of the Pyruvate and the alpha-Ketoglutarate Dehydrogenase Complexes of Corn (Zea mays L.) and Soybean (Glycine max [L.] Merr.)
Plant Physiol 1988 Jun;87(2):334-40.PMID:16666143DOI:10.1104/pp.87.2.334.
The grass-specific herbicide Haloxyfop, ((+/-)-2-[4-((3-chloro-5-(trifluoromethyl)-2-pyridinyl)oxy)-phenoxy] propionic acid) has been shown to inhibit lipid synthesis and respiration, to cause the accumulation of amino acids, and not to affect cellular sugar or ATP levels. Thus studies were carried out with enzyme activities from corn (Zea mays L.) (Haloxyfop sensitive) and soybean (Glycine max [L.] Merr.) (Haloxyfop tolerant) to locate the possible inhibition sites among the glycolytic and tricarboxylic acid (TCA) cycle enzymes. Following along the oxidative metabolism pathway of sugars, the pyruvate dehydrogenase complex (PDC) was the first enzyme among the glycolytic enzymes that demonstrated noticeable inhibition by 1 millimolar Haloxyfop. Kinetic studies with corn and soybean PDC from both purified etioplasts and mitochondria gave K(i) values of from 1 to 10 millimolar. Haloxyfop also inhibited the activity of the TCA cycle enzyme, the alpha-ketoglutarate dehydrogenase complex (alpha-KGDC) which carries out the same reaction as PDC except for the substitution of alpha-ketoglutarate for pyruvate as one of the substrates. The K(i) values were somewhat lower in this case (near 1 millimolar). The relatively high K(i) values for both enzyme complexes would indicate that these may not be the herbicidal sites of inhibition, but it is possible that the herbicide could be concentrated in compartments and/or the substrate concentrations may be well below optimal. Likewise little difference was seen in the Haloxyfop inhibition of the enzyme activities from the sensitive species, corn, and from the tolerant species, soybean, so the selectivity of the herbicide is not evident from these results. The inhibition of the PDC and alpha-KGDC as the mode of action of Haloxyfop is, however, consistent with the observed physiological effects of the herbicide, and these are the only enzymic activities so far found to be sensitive to Haloxyfop.
Environmental behavior of the chiral herbicide Haloxyfop. 1. Rapid and preferential interconversion of the enantiomers in soil
J Agric Food Chem 2015 Mar 18;63(10):2583-90.PMID:25742319DOI:10.1021/jf505241t.
Haloxyfop-methyl is a chiral herbicide that was first introduced as racemate and later replaced by "haloxyfop-P-methyl", mainly consisting of the R-enantiomer, which carries the herbicidal activity. We studied the ester cleavage of haloxyfop-methyl and further degradation and chiral inversion of the acid enantiomers in three different soils using enantioselective gas chromatography-mass spectrometry. Our results confirm the rapid ester hydrolysis of haloxyfop-methyl with half-lives of a few hours and indicate that hydrolysis is weakly enantioselective. Further degradation of Haloxyfop was slower with half-lives of several days. In all three soils, S-haloxyfop was rapidly converted to R-haloxyfop. In sterile soil, no degradation and no inversion were observed, indicating that both processes are biologically mediated. In soil where 50% of the water had been replaced by deuterium oxide, significant H-D exchange in Haloxyfop was observed, pointing to a reaction mechanism involving abstraction of the proton at the chiral center of the molecule.