Degradation of the sulfonylurea herbicides chlorsulfuron and triasulfuron in a high-organic-matter volcanic soil

The degradation rates of two sulfonylurea herbicides, chlorsulfuron and triasulfuron, were determined at two application rates, 15 and 30 g a.i. ha^–1, in a sandy loam soil of volcanic origin under controlled environment and field conditions. Residues were measured using a modified gas chromatographic (gc) determination method. Both herbicides degraded rapidly in the acidic soil (pH 5.7) with high organic matter levels (7.3% o.m.), generally according to first-order rate kinetics. The respective half-lives ranged from 22 to 38 d for chlorsulfuron and from 31 to 44 d for triasulfuron under five controlled temperature/soil moisture regimens, ranging from 10 to 30 °C and between 40% and 80% maximum water-holding capacity. Half-lives in the field were considerably shorter (13 d for chlorsulfuron and 12–13 d for triasulfuron). The degradation rates of the herbicides were influenced more by soil temperature than by soil moisture content. Bioassays using white mustard ( Sinapis alba L.) and forage sorghum [ Sorghum bicolor (L.) Moench] were also used to determine the persistence of phytotoxic residues of both herbicides in the field, and the results showed that the effects of chlorsulfuron disappeared within 8 weeks. Triasulfuron residues disappeared within 9 and 14 weeks for the 15 and 30 g a.i. ha^–1 rates respectively.     

70%醚苯磺隆水分散粒剂的反相高效液相色谱测定

本文叙述了采用反相高效液相色谱外标法,以甲醇-水为流动相,用C18柱和紫外检测器(240nm),测定70%醚苯磺隆水分散粒剂的含量的方法。结果表明:方法的标准偏差为:0.072,变异系数为:0.10%,平均回收率为99.86%。线性相关系数为:0.9991。     

Photodegradation of herbicide triasulfuron

Triasulfuron was degraded in aqueous solution by ultraviolet irradiation to yield 2-chloroethoxybenzene and (4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea. The reaction followed first-order kinetics. In sunlight, the reaction was slower and afforded these two photoproducts together with 2-amino-4-methoxy-6-methyltriazine and 2-(2-chloroethoxy)benzenesulfonamide. The latter compounds arise from hydrolytic cleavage of the sulfonylurea bridge of triasulfuron because of the acidity of the reaction medium due to the loss of sulfur dioxide. A mechanism which accounts for the formation of the photoproducts is proposed. © 1999 Society of Chemical Industry     

Characterization of a Spontaneous Rapeseed Mutant Tolerant to Sulfonylurea and Imidazolinone Herbicides

A spontaneous chlorsulfuron tolerant variant, RCS-5, was isolated from protoplast culture of rapeseed, Brassica napus L. The tolerance level of the mutant was due to mutation of a single dominant gene resulting in an alteration of the acetolactate synthase enzyme. Seedling growth bioassays applied in vitro or after seed-soaking treatment showed that the mutant was 250——500 more tolerant to chlorsulfuron than the sensitive control. Field tolerance was evaluated with commercial formulations of chlorsulfuron (Glean T), triasulfuron (Kéos), and metsulfuron methyl (Allié), and an imidazolinone imazamethabenz (Méganet). The results indicated that the mutant could tolerate a lower dose rate of sulfonylureas than the dose recommended for cereal culture. In contrast, the mutation provided a good protection against imazamethabenz. The possibility of using the protoplast-derived mutation in crop rotation and F1 hybrid seed purity assessment is also discussed. However, isolated lines of the mutant were found to be less productive and one week later than the sensitive parent.     

Comparison of sulfonylurea herbicide residue detection in soil by bioassay, enzyme-linked immunosorbent assay and hplc

The ability of bioassay, enzyme-linked immunosorbent assay (ELISA) and high-performance liquid chromatography (hplc) methods to detect sulfonylurea herbicides in soil was evaluated as part of a project studying the leaching and persistence of these herbicides in the alkaline soils of south-eastern Australia. Soil samples with known concentrations between 0.1 and 10 μg a.i. kg⁻¹ chlorsulfuron, metsulfuron-methyl or triasulfuron were prepared by an independent laboratory and supplied in coded bags to separate laboratories for testing. The accuracy of the results was analysed, and the merits of each method are discussed. Bioassay was suitable for measuring biologically active residues from 0.1 to 1.0 μg a.i. kg⁻¹. ELISA accurately measured residues in the range of 0.1–10 μg a.i. kg⁻¹, making it the most widely adaptable assay tested. It will be useful for measuring residues in sodic subsoils where bioassay plants grow poorly. There was good reproducibility between the bioassay and ELISA. The hplc technique used in this study was not as accurate as bioassay or ELISA at quantifying residues of 3.0–10 μg a.i. kg⁻¹ and could not detect residues at or below 1.0 μg a.i. kg⁻¹.     

绿磺隆、醚苯磺隆及其体外代谢物对乙酰乳酸合成酶的离体抑制作用

利用异源表达于酵母细胞中的小麦细胞色素P450cDNA(CYP71C6v1)研究了磺酰脲类除草剂绿磺隆、醚苯磺隆的代谢作用。结果表明,代谢产物5-羟基绿磺隆和5-羟基醚苯磺隆能够抑制乙酰乳酸合成酶(ALS酶)活性,且代谢产物与母体化合物绿磺隆、醚苯磺隆抑制ALS酶活性的IC50值差异小,但是代谢产物在茎叶喷雾小麦和菜豆时,均未表现出活性。绿磺隆及其代谢产物抑制小麦ALS酶活性的IC50值分别为7.1×10-9和7.9×10-9mol/L,抑制菜豆ALS酶活性的IC50分别为3.6×10-9和4.1×10-9mol/L;醚苯磺隆及其代谢产物抑制小麦ALS酶活性的IC50分别为4.6×10-9和5.3×10-9mol/L,抑制菜豆ALS酶活性的IC50分别为4.7×10-9和4.9×10-9mol/L。结果表明,在磺酰脲类分子苯环5位上进行结构改造,有可能得到高活性的化合物。