CN114766485A - 半刚性酰腙配体在除草剂中的应用及一种基于半刚性酰腙配体的复合除草剂 - Google Patents
半刚性酰腙配体在除草剂中的应用及一种基于半刚性酰腙配体的复合除草剂 Download PDFInfo
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Classifications
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- A—HUMAN NECESSITIES
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- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/46—N-acyl derivatives
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/46—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom rings with more than six members
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
- A01N59/02—Sulfur; Selenium; Tellurium; Compounds thereof
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- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
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Abstract
本发明属于化学农药技术领域,本发明提供了半刚性酰腙配体在除草剂中的应用及一种基于半刚性酰腙配体的复合除草剂。本发明的复合除草剂包括如下重量份的原料:半刚性酰腙配体30~50份,增效剂15~30份,分散剂1~10份,润湿剂1~10份,安全剂1~5份,水70~100份。本发明制备的复合除草剂具有成本低、水溶性好以及除草活性高等优点。
Description
技术领域
本发明涉及化学农药技术领域,尤其涉及半刚性酰腙配体在除草剂中的应用及一种基于半刚性酰腙配体的复合除草剂。
背景技术
杂草防治是保护现代农业生产的关键措施之一,化学除草剂的产生和发展大大加强了农业生产的保障,并提高了农业生产效益,目前,新型除草剂仍然是农药领域的热门研究课题。化学除草剂的优势在于可以选择性的杀死杂草而不伤害农作物,能够大大减轻劳动强度,节省人工,有效地控制杂草的滋生与蔓延,从而保护农业生产,提高农业经济效益。
酰腙类化合物是酰肼与醛或酮缩合而成的一类Schiff碱类化合物,分子结构中存在Schiff碱基和酰胺键等活性基团,所以其具有独特的消炎、杀菌、抗惊厥、抗肿瘤、抗糖尿病、抗结核病菌等生物活性,良好的非线性发光特性,以及与过渡金属或稀土金属等强的配位能力,在农药、医药、分析、催化和材料等方面具有广泛的应用。但是,目前尚未筛选出一种包含酰腙类化合物的具有高效、安全、经济等优点的除草剂。
因此,如何制备一种高效、安全、经济的除草剂成为了本领域技术人员亟需解决的问题。
发明内容
有鉴于此,本发明提供了半刚性酰腙配体在除草剂中的应用及一种基于半刚性酰腙配体的复合除草剂。本发明第一个目的是为半刚性酰腙配体的应用提供一种新的途径;第二个目的则是解决现有除草剂见效时间长、除草活性低的技术问题。
为了达到上述目的,本发明采用如下技术方案:
本发明提供了半刚性酰腙配体在除草剂中的应用,所述半刚性酰腙配体的结构式如下:
本发明还提供了一种基于半刚性酰腙配体的复合除草剂,包括如下重量份的原料:
半刚性酰腙配体30~50份,增效剂15~30份,分散剂1~10份,润湿剂1~10份,安全剂1~5份,水70~100份;
所述半刚性酰腙配体的结构式如下:
进一步的,所述增效剂为苯基磺酰脲、硫酸铵或氮酮。
进一步的,所述分散剂为聚羧酸钠盐或木质素磺酸盐。
进一步的,所述润湿剂为十二烷基苯磺酸钠、皂角粉或茶枯。
进一步的,所述安全剂为双苯噁唑酸、赤霉酸或解毒喹。
进一步的,所述复合除草剂的剂型为悬浮剂、微乳剂、水乳剂、乳油剂或水分散粒剂。
经由上述的技术方案可知,与现有技术相比,本发明的有益效果如下:
1、本发明所使用的原料为环境友好型,所制备的复合除草剂容易降解,对环境无污染;
2、本发明添加了增效剂,增效剂可以弱化或者抑制杂草对于复合除草剂的抗性,从而减缓药剂在杂草体内的代谢速度,增强复合除草剂的除草活性;本发明添加的润湿剂配合增效剂可提高药物的分散效果,从而令复合除草剂的成分保持稳定,有利于复合除草剂的释放及吸收;本发明所使用的安全剂,在不影响复合除草剂的除草活性的前提下,可选择性的保护农作物不受除草剂的危害;
3、较现有的复合除草剂,本发明制备的复合除草剂的成本更低,水溶性更好,除草活性更高。
具体实施方式
本发明提供了半刚性酰腙配体在除草剂中的应用,所述半刚性酰腙配体的结构式如下:
本发明还提供了一种基于半刚性酰腙配体的复合除草剂,包括如下重量份的原料:
半刚性酰腙配体30~50份,增效剂15~30份,分散剂1~10份,润湿剂1~10份,安全剂1~5份,水70~100份。
在本发明中,所述重量份的原料优选为:半刚性酰腙配体35~45份,增效剂18~27份,分散剂2~8份,润湿剂2~8份,安全剂2~4份,水75~90份。
在本发明中,所述重量份的原料进一步优选为:半刚性酰腙配体38~42份,增效剂20~25份,分散剂4~6份,润湿剂4~6份,安全剂3份,水80~88份。
在本发明中,所述半刚性酰腙配体的结构式如下:
在本发明中,所述半刚性酰腙配体的制备方法如下:
S1、在保护气体下,将甘氨酸乙酯盐酸盐、三乙胺、无水二氯甲烷和草酰氯单乙酯溶液混合后进行反应,得到3-((2-乙氧基-2-氧乙基)氨基)-3-氧代丙酸乙酯;
S2、将3-((2-乙氧基-2-氧乙基)氨基)-3-氧代丙酸乙酯、水合肼和乙醇混合后进行反应,得到2-肼基-N-(2-肼基-2-氧代乙基)-2-氧代乙酰胺;
S3、将2-肼基-N-(2-肼基-2-氧代乙基)-2-氧代乙酰胺、3-乙氧基-2-羟基苯甲醛和乙醇混合后进行反应,即得半刚性酰腙配体;
在步骤S1中,所述保护气体为氮气、氩气、氦气、氖气和二氧化碳中的一种,优选为氮气或氩气,进一步优选为氮气。
在本发明中,所述草酰氯单乙酯溶液的浓度为0.5~2mmol/mL,优选为1.0~1.8mmol/mL,进一步优选为1.2~1.5mmol/mL。
在本发明中,所述甘氨酸乙酯盐酸盐、三乙胺、无水二氯甲烷和草酰氯单乙酯溶液的质量体积比为(2.5~3.5)g:(7~10)mL:(90~110)mL:(15~30)mL,优选为(2.8~3.2)g:(8~9)ml:(95~100)ml:(20~25)ml。
在本发明中,所述步骤S1反应的温度为-5~2℃,优选为-4~1℃,进一步优选为-3~0℃;反应的时间为8~15h,优选为10~12h,进一步优选为11h;
在步骤S2中,在所述3-((2-乙氧基-2-氧乙基)氨基)-3-氧代丙酸乙酯、水合肼和乙醇的质量体积比为(1.5~3)g:(2~4)g:(30~60)mL,优选为(2~2.3)g:(2.5~3.5)g:(40~50)ml。
在本发明中,所述步骤S2反应的温度为70~90℃,优选为75~85℃,进一步优选为78~82℃;反应的时间为8~15h,优选为9~12h,进一步优选为10h;
在步骤S3中,所述2-肼基-N-(2-肼基-2-氧代乙基)-2-氧代乙酰胺、3-乙氧基-2-羟基苯甲醛和乙醇的质量体积比为(0.5~2)g:(1.5~3)g:(30~60)mL,优选为(0.8~1)g:(1.8~2.5)g:(40~50)ml。
在本发明中,所述步骤S3反应的温度为70~90℃,优选为75~85℃,进一步优选为78~82℃;反应的时间为6~12h,优选为8~10h,进一步优选为9h。
在本发明中,所述增效剂为苯基磺酰脲、硫酸铵或氮酮,优选为苯基磺酰脲或硫酸铵,进一步优选为硫酸铵。
在本发明中,所述分散剂为聚羧酸钠盐或木质素磺酸盐,优选为木质素磺酸盐,进一步优选为木质素磺酸钠或木质素磺酸钙。
在本发明中,所述润湿剂为十二烷基苯磺酸钠、皂角粉或茶枯,优选为十二烷基苯磺酸钠或皂角粉,进一步优选为皂角粉。
在本发明中,所述安全剂为双苯噁唑酸、赤霉酸或解毒喹,优选为双苯噁唑酸或赤霉酸,进一步优选为双苯噁唑酸。
在本发明中,所述复合除草剂的剂型为悬浮剂、微乳剂、水乳剂、乳油剂或水分散粒剂,优选为悬浮剂、水乳剂、乳油剂或水分散粒剂,进一步优选为悬浮剂、水乳剂或水分散粒剂。
下面将对本发明实施例中的技术方案进行清楚、完整地描述,显然,所描述的实施例仅仅是本发明一部分实施例,而不是全部的实施例。基于本发明中的实施例,本领域普通技术人员在没有做出创造性劳动前提下所获得的所有其他实施例,都属于本发明保护的范围。
实施例1~5及对比例1所使用的半刚性酰腙配体,其具体制备步骤如下:
S1、向装有搅拌棒和加料漏斗的250mL三颈烧瓶中,加入2.8g的甘氨酸乙酯盐酸盐,8.0mL的三乙胺和95mL的无水二氯甲烷。在冰水浴氩气(Ar)保护条件下,向该混合物体系中滴加20mL含有2.73g(0.02mol)草酰氯单乙酯的无水二氯甲烷溶液,滴加速度控制在半小时。将所得溶液在0℃下搅拌8h,并通过添加50mL的蒸馏水将反应淬灭。混合物用饱和碳酸氢钠水溶液洗涤,同时加入适量的蒸馏水进行分液萃取,有机层用无水硫酸钠干燥,并使用旋转蒸发仪浓缩,即得中间体3-(2-乙氧基-2-氧乙基)氨基)-3-氧代丙酸乙酯。
S2、将2g 3-((2-乙氧基-2-氧代乙基)氨基)-3-氧代丙酸乙酯,2.5g质量分数为80%的水合肼,以及40mL乙醇溶液中置于100mL的圆底烧瓶中。将混合物溶液在回流条件下搅拌,搅拌温度为78℃。反应10小时,然后冷却至室温。过滤分离粗产物,再用冷乙醇洗涤三次,得到白色固体2-肼基-N-(2-肼基-2-氧代乙基)-2-氧代乙酰胺。
S3、将1.8g的3-乙氧基-2-羟基苯甲醛和40mL乙醇加入到100mL的圆底烧瓶中,再加入0.8g的2-肼基-N-(2-肼基-2-氧代乙基)-2-氧代乙酰胺,然后将混合物体系在75℃条件下回流10小时。反应结束后冷却至室温,过滤出白色固体,再用冷甲醇洗涤3次,并在空气中干燥,即得半刚性酰腙配体。
经计算,步骤S1的转化率为65.2%,步骤S2的转化率为95.1%,步骤S3的转化率为88.3%。
实施例1
本实施例的复合除草剂,包括如下重量份的原料:
半刚性酰腙配体35份,硫酸铵20份,木质素磺酸钙3份,皂角粉4份,双苯噁唑酸2份,水80份。
实施例2
本实施例的复合除草剂,包括如下重量份的原料:
半刚性酰腙配体40份,苯基磺酰脲15份,木质素磺酸钠6份,茶枯5份,赤霉酸3份,水75份。
实施例3
本实施例的复合除草剂,包括如下重量份的原料:
半刚性酰腙配体30份,氮酮25份,木质素磺酸钙8份,十二烷基苯磺酸钠2份,解毒喹2份,水85份。
实施例4
本实施例的复合除草剂,包括如下重量份的原料:
半刚性酰腙配体45份,苯基磺酰脲25份,木质素磺酸钙3份,十二烷基苯磺酸钠4份,双苯噁唑酸3份,水95份。
实施例5
本实施例的复合除草剂,包括如下重量份的原料:
半刚性酰腙配体50份,硫酸铵15份,木质素磺酸钠2份,茶枯8份,解毒喹4份,水100份。
对比例1
本对比例与实施例1相比,未添加增效剂,其余原料及用量相同。
性能测试
将实施例1~5和对比例1制备的复合除草剂分别对水稻田进行喷洒(15kg/亩),观察喷洒后的稗草和马唐的生长情况,结果如表1所示。
表1复合除草剂的除草效果
由表1可知,本发明制备的复合除草剂对稗草的死亡率在97.1~98.6%之间,马唐的死亡率在96.5~97.9%之间,在3~5天之内即可见效;而对比例1对稗草的死亡率仅为75.9%,马唐的死亡率仅为72.8%,并且在20天的时候才能见效。由此表明,本发明制备的复合除草剂见效更快,除草效果更好。
本说明书中各个实施例采用递进的方式描述,每个实施例重点说明的都是与其他实施例的不同之处,各个实施例之间相同相似部分互相参见即可。
对所公开的实施例的上述说明,使本领域专业技术人员能够实现或使用本发明。对这些实施例的多种修改对本领域的专业技术人员来说将是显而易见的,本文中所定义的一般原理可以在不脱离本发明的精神或范围的情况下,在其它实施例中实现。因此,本发明将不会被限制于本文所示的这些实施例,而是要符合与本文所公开的原理和新颖特点相一致的最宽的范围。
Claims (7)
3.根据权利要求2所述的复合除草剂,其特征在于,所述增效剂为苯基磺酰脲、硫酸铵或氮酮。
4.根据权利要求2或3所述的复合除草剂,其特征在于,所述分散剂为聚羧酸钠盐或木质素磺酸盐。
5.根据权利要求4所述的复合除草剂,其特征在于,所述润湿剂为十二烷基苯磺酸钠、皂角粉或茶枯。
6.根据权利要求2、3或5所述的复合除草剂,其特征在于,所述安全剂为双苯噁唑酸、赤霉酸或解毒喹。
7.根据权利要求6所述的复合除草剂,其特征在于,所述复合除草剂的剂型为悬浮剂、微乳剂、水乳剂、乳油剂或水分散粒剂。
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