磺酰脲类除草剂的合成及其除草活性

磺酰脲类除草剂具有用量低,活性高、选择性好、毒性小的优点。为开发和应用此类除草剂,我们合成了在氮原子上连正丁基的8个新的衍生物,并进行了室内药效测定。     

含嘧啶环的噻吩磺酰脲的合成和除草活性测定

从噻吩出发经4步反应合成了15种含嘧啶的噻吩磺酰脲N’-(4,6-二取代嘧啶-2-基)-2-噻吩磺酰脲,其中11种为未见文献报道的新化合物.其结构经红外光谱、~1H NMR谱和元素分析证实.初步生物活性试验表明,这类化合物具有较好的除草活性.     

磺酰脲类化合物除草活性的QSAR研究

采用密度泛函理论方法, 在B3LYP/6-31G(d)水平下, 计算了23种磺酰类化合物的分子极化率及分子骨架中各原子的Milliken电荷. 提出了一种新的QSAR建模方法, 并据此对其中18种化合物进行多元线性回归分析, 建立了除草活性的预测模型(R=0.96, R2=0.92, r2adj=0.88, F=26.26, q2=0.71, p<0.01, SE=0.36), 对剩余五种化合物进行预测, 结果吻合. 该模型从化合物的亲水性、分子几何特征的角度对如何提高磺酰脲类化合物的除草活性进行了分析, 并对提高化合物除草活性的方法做出预测: 提高苯环和嘧啶环取代基的亲水性, 增加N13周围的电子云密度, 为苯环接入较小的取代基团, 在嘧啶环上接入较大取代基团都可提高化合物的除草活性. 预测结果与3D-QSAR方法的预测结果一致.     

新磺酰脲类化合物的合成及除草活性

新磺酰脲类化合物的合成及除草活性;嘧啶;合成;除草剂     

N，N＇－硫代磷酰基芳酰胺基硫脲的合成及生物活性

Ｎ，Ｎ＇－硫代磷酰基芳酰胺基硫脲的合成及生物活性金桂玉，解敏雨，赵国锋（南开大学元素有机化学研究所天津３０００７１）关键词芳酰肼，硫代磷酰基异硫氰酸酯，硫代磷酰基芳酰胺基硫脲，合成，生物活性含（硫代）磷酰基的硫脲衍生物具有广泛生物活性，如杀虫［１，２...     

三氟甲基嘧啶磺酰脲的合成与除草活性

以三氟乙酰乙酸乙酯和盐酸胍为原料,经环合、氯化、甲氧基化、胺化反应合成了4种2-氨基-4-取代-6-三氟甲基嘧啶中间体(Ⅰa~Ⅰd),Ⅰ与邻甲氧羰基苯磺酰异氰酸酯亲核加成,合成了3种含不同取代嘧啶环的磺酰脲化合物(Ⅱb~Ⅱd)。其中2-氨基-4-二甲胺基-6-三氟甲基嘧啶(Ⅰd)和N[-2-(′4-二甲胺基-6-三氟甲基)嘧啶基]-2-甲氧羰基苯磺酰脲(Ⅱd)为新化合物,结构经1H NMR和MS表征。初步除草活性测定结果表明,N-[2-′(4-甲氧基-6-三氟甲基)嘧啶基]-2-甲氧羰基苯磺酰脲(Ⅱc)在浓度为200 ga.i./ha时对稗草和马唐的防效分别为70%和50%。     

苯环2-位不同酯基取代的磺酰脲类化合物的合成及其除草活性

以正在开发的磺酰脲类超高效除草剂NK94827[N'-(4'-甲基嘧啶-2'-基)-2-甲氧羰基苯磺酰脲]的基本结构为基础,设计合成了18个苯环2位不同酯基取代的的新型磺酰脲类化合物,产物结构均经¹HNMR及元素分析确证.经油菜平皿法和盆栽试验测试除草活性,所合成的部分磺酰脲化合物的除草活性高.     

嘧啶基苯硫甲基磺酰脲化合物的合成及除草活性

４，６－二氯－２－嘧啶基苯硫甲基磺酰脲与甲醇钠反应，合成了１５个 见文献报道的标题化合物。它们的结构经ＩＲ，＾１ＨＮＭＲ，ＭＳ，元素分析证实。其中一类化合物具有较强除草活性。     

含有单取代嘧啶的新型磺酰脲类化合物的设计、合成及除草活性

为了寻找高效的磺酰脲类除草剂, 以商品化磺酰脲类除草剂为基础, 将单取代嘧啶结构引入到分子中, 合成了一系列新型磺酰脲类化合物, 并通过¹H NMR和高分辨质谱确定了其结构. 采用盆栽法和平皿法测试了所有化合物的除草活性以及部分化合物对油菜的IC₅₀值. 结果表明, 一些化合物具有一定的除草活性, 其中化合物7b和7d对油菜和反枝苋具有较好的抑制活性.     

含嘧啶环的苯基磺酰脲、吡唑磺酰脲的合成及生物活性

磺酰脲衍生物;除草活性;含嘧啶环的苯基磺酰脲、吡唑磺酰脲的合成及生物活性     

Synthesis and Herbicidal Activity of Novel Sulfonylureas Containing Thiadiazol Moiety

Thirteen novel sulfonylureas containing thiadiazole moiety were synthesized in a two-step reaction. Their structures were determined using IR, ^1H NMR, HRFTMS, and elemental analysis. Herbicidal activities of these compounds were determined in the green house bio-assay. The results show that four compounds among them exhibit some activity toward four tested herbs.     

Synthesis and Herbicidal Activity of Novel Sulfonylureas Containing 1,2,4-Triazolinone Moiety

A series of new sulfonylureas incorporating 1,2,4-triazolinone moiety was synthesized, which were further bio-assayed for the herbicidal activity against four herbs, representative of monocotyledons and dicotyledons. Some of them exhibited high potency to inhibit the growth of dicotyledons(Bassica napus and Amaranthus retroflexus) in the pot experiment. Compounds 9a and 9b also displayed an excellent herbicidal activity against Bassica napus at a concentration of 15 g/hectare, which were comparable with commercial triasulfuron.     

Design,Synthesis and Herbicidal Activity of Novel Sulfonylureas Containing Tetrahydrophthalimide Substructure

To develop novel sulfonylurea herbicides, a series of chlorsulfuron derivatives was designed and synthesized through introducing tetrahydrophthalimide substructure taken from protoporphyrinogen IX oxidase(PPO) inhibitors onto the critical 5-position of the classical benzene ring. The structures of title compounds were confirmed by infrared spectroscopy, ultraviolet spectroscopy, ¹H and ¹³C NMR spectrometry, mass spectrometry and elemental analysis. In addition, the crystal structure of compound II-5 was further determined by X-ray diffraction analysis. Bioassay results showed that individual compounds exhibited good herbicidal activities, especially compound II-8, which displayed 100% inhibition rate against Echinochloa crusgalli at 150 g/ha(1 ha=10⁴ m²) with the method of foliage spray in the pot experiment.     

含十五内酯环磺酰脲类化合物的合成

为模拟天然产物的结构, 以α-硝基环十二酮为原料, 通过与丙烯醛的Michael加成、扩环和引入磺酰脲的侧链, 合成了五个含十五内酯环的磺酰脲类化合物4. 它们的结构均通过¹H NMR, IR和元素分析确证. 生测结果表明它们均具有一定的除草活性. 其中以4c的活性最高, 对马唐和苘麻的LC₅₀分别为27.4和71.8 mg/L.     

Design,Synthesis and Herbicidal Activity of Novel Sulfonylureas Containing Triazole and Oxadiazole Moieties

Three novel series of 5-substituted sulfonylurea derivatives were designed and synthesized via introducing a triazole or oxadiazole ring at the 5th position of the benzene ring in classical sulfonylurea herbicides. All the target compounds were confirmed by means of ¹H nuclear magnetic resonance(NMR), ¹³C NMR and elemental analysis. The bioassay results show that the target compounds containing an oxadiazole ring at the 5th position display moderate to excellent herbicidal activities against Brassica campestris and Amaranthus retroflexus under soil treatment. Especially, compounds zdk20, zdk21 and zdk22 possess 98.6%, 96.5% and 94.5% inhibition rates, respectively, against Amaranthus retroflexus at a concentration of 75 g/ha(1 ha=1×10⁴ m²) under soil treatment, which approach to those of the commercial herbicide chlorsulfuron.