Studies Of Pesticidal Properties Of Tosyl- P – Amino Phenol And – P –Nitro Phenol

H.D. Aliyu

摘要

The tosylated compounds of p-nitrophenol and p-aminophenol were characterized by NMR and IR spectroscopy and their physical properties determined. Both compounds are highly toxic with Lc50 less than 50.0μg/ml. their insecticidal and herbicidal activities of the compounds are promising. Introduction In the evolution of agriculture towards intensive monoculture, there has been a trend away from the traditional method of pest control such as crop rotation, stalk destruction, elimination of pest habitat and use of tolerant crop variety, to almost complete dependence on pesticides (1). In many part of the world, especially the third world countries, pest has become a major agricultural problem that threatens crops and farm animals. Although various techniques were employed on the combat against pest (9) The chemical method will continue to be the major method of pest and diseases control in agriculture world wide, in spite of its many disadvantages especially environmental pollution.Most pesticides are broad band toxicants; any selectivity they may have is derived from the manner in which they are used than for inherent properties. Although it is conceivable that those highly selective poisons could be developed for pest and a few examples are known, e.g Antu for rat [2]. They can however be grouped into two main classes, the contact or non-systematic pesticides and systematic pesticides.Agricultural products most be produced in such quantities, that will be enough for the food need of our ever increasing population, as well as, industrial raw material (2). For this reason there is the need for producing a chemical which is more effective on pest and less harmful to man, for preventing this undesirable elements, either by retarding their growth or eliminating them completely (3).Many derivatives of toluene suphoxy compound have been synthesized by many workers in pyridine (4,7). Since most known pesticides contains such groups as NO2, and SO3. This necessitated the synthesis of these compounds, and their activity against shrimps, bean weevil, rat, maize and bean seeds as reported in this work. Materials Methods The chemicals used are products of Andrich Chemical Company. The IR was run with peerkin-elmer 577 instrument, Nmr by nmr 317B. While the UV was run on sp 750 UV – Visible spectrometer. The SO3 were determined titrimetrically according to standard procedure (8).Synthesis of toluene-p-sulphonoxy-p-nitrophenol (A)40 ml of pyridine was added to p-nitrophenol in a 500ml conical flask. The mixture was cooled to 0 °C in an bath continuous swirling, and 40.60g of toluene-p-surphonic acid was added gently. The mixture was allowed to stand for six hours, with continuous swirling in the ice bath. 100ml of diethl ether was added as solvent and the part which contained the product, was separated from the aqueous layer using a separating funnel. 50ml of dilute hydrochloric acid was added to the organic layer in the separating funnel to remove the pyridine. This was repeated thrice until the odour of pyridine was no longer observed.Anhyfrous sodium sulphate was added as a drying agent to remove water molecules and the sulphate salt was filtered off and concentrated under vacuoo, leaving a brown solid 12.195% (mpt 90 °C )v max1580 (C=O aryl), 1360 (-SO3-C), 8500 (ph-NO2), H 1 nmr (CDCl3 + Tms) δ7.6 (4H,S aryl) 2.2 (CH3), λmax 458nm, SO3 27.38% (27.30%).Toluene-p-sulphonoxy-3-aminophenol (B)40ml of pyridine was added to 40g of 4-Aminophenol in a 500ml conical flask. The mixture was cooled to 0 °C in an ice bath with continuous swirling, and 62.82g of toluene-p-sulphonicc acid was added gently and treated as in the above procedure, resulting in a brown solid, 18.72% (m.p 82 °C ) v max (Nujol), 1570 (C=C, aryl), 3150 (Ph-NH), 1365 (SO3-C) 1 Hnmr (CDCl3 + TMS) δ: 7.4 (4H, S, aromatic), 2.2 (CH3), 6.2 (NH – aryl) λmax 445nm, SO3, 30.82% (30.42%).Lethal Dose20 brine shrimp eggs were added to the hatching chamber of a hatching vial and kept under

机译：对硝基苯酚和对氨基苯酚的甲苯磺酸化化合物通过NMR和IR光谱进行表征，并确定其物理性质。两种化合物均具有高毒性，Lc50低于50.0μg/ ml。这些化合物的杀虫和除草活性很有希望。引言在农业向集约化单一栽培的演变过程中，已出现了从传统的虫害控制方法（例如轮作，秸秆破坏，消除虫害栖息地和使用耐受性作物品种）到完全完全依赖农药的趋势（1 ）。在世界许多地方，尤其是第三世界国家，虫害已成为威胁农作物和农场动物的主要农业问题。尽管人们采用了多种技术来防治有害生物（9），但化学方法将继续成为全世界农业上控制病虫害的主要方法，尽管它有许多不利条件，尤其是对环境的污染。它们可能具有的任何选择性均源自其使用方式，而非固有性质。尽管可以想到可以开发出具有高度选择性的毒物用于害虫，并且已经知道了一些例子，例如大鼠的Antu [2]。但是，它们可以分为接触农药或非系统农药和系统农药两大类。农产品的生产量最大，足以满足我们不断增长的人口的食品需求以及工业原料。材料（2）。因此，需要生产一种对有害生物更有效，对人类危害较小的化学物质，以通过阻止其生长或完全消除它们来防止这种不良元素的产生（3）。由许多工人合成吡啶（4,7）。由于大多数已知的农药都含有诸如NO2和SO3之类的基团。正如这项工作所报道的，这需要合成这些化合物，以及它们对虾，豆象鼻虫，大鼠，玉米和豆类种子的活性。物料方法所用化学品是Andrich Chemical Company的产品。 IR用NMR 317B的peerkin-elmer 577仪器运行。当在sp 750 UV –可见光谱仪上运行UV时。根据标准程序（8）滴定确定SO3的含量。甲苯-对-磺酰氧基-对硝基苯酚（A）的合成在40 ml锥形烧瓶中，将40 ml吡啶加入对硝基苯酚中。在连续涡旋浴中将混合物冷却至0℃，并缓慢加入40.60g的甲苯-对-磺酸。将混合物静置六小时，在冰浴中连续涡旋。加入100ml的二乙醚作为溶剂，并使用分液漏斗将包含产物的部分与水层分离。将50ml的稀盐酸加入到分液漏斗中的有机层中以除去吡啶。重复三次，直到不再观察到吡啶的气味。加入无水硫酸钠作为干燥剂以除去水分子，将硫酸盐滤出并真空浓缩，得到褐色固体12.195％（mpt 90°C））v max1580（C = O芳基），1360（-SO3-C），8500（ph-NO2），H 1 nmr（CDCl3 + Tms）δ7.6（4H，S芳基）2.2（CH3），λmax458nm， SO3 27.38％（27.30％）。甲苯-对-磺酰氧基-3-氨基苯酚（B）将40ml吡啶加入到500ml锥形烧瓶中的40g 4-氨基苯酚中。将混合物在冰浴中连续涡旋冷却至0°C，然后缓慢加入62.82 g甲苯-对磺酸，并按上述步骤处理，得到褐色固体，为18.72％（mp 82°C ）v max（Nujol），1570（C = C，芳基），3150（Ph-NH），1365（SO3-C）1 Hnmr（CDCl3 + TMS）δ：7.4（4H，S，芳族），2.2（CH3 ），6.2（NH-芳基）λmax445nm，SO3，30.82％（30.42％）。致死剂量20盐水虾卵被添加到孵化瓶的孵化室中并保持在

Studies Of Pesticidal Properties Of Tosyl- P – Amino Phenol And – P –Nitro Phenol

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