CN117105908B - 一种双酰胺杀虫剂及应用 - Google Patents
一种双酰胺杀虫剂及应用 Download PDFInfo
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- CN117105908B CN117105908B CN202311373056.7A CN202311373056A CN117105908B CN 117105908 B CN117105908 B CN 117105908B CN 202311373056 A CN202311373056 A CN 202311373056A CN 117105908 B CN117105908 B CN 117105908B
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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Abstract
本发明公开一种式I化合物和其盐及立体异构体,其中,R1选自羟基、硝基、卤代(C1‑C6)烷氧基和(C1‑C6)烷磺酸基中一种,R2选自卤素和(C1‑C6)烷磺酸基中一种。本发明化合物具有优异的杀虫效果,杀虫起效快,杀虫时效长。
Description
技术领域
本发明涉及农药领域,具体涉及一种双酰类化合物或其盐类为有效成分的农业用杀虫剂或者动物用的外部或内部寄生虫防除剂、及它们的使用方法。
背景技术
双酰胺类杀虫剂作用于昆虫体内的鱼尼丁受体抑制剂,能使害虫过度的释放肌体细胞中的钙离子,由于释放的钙离子浓度持续上升会引发害虫体内的“肌肉”收缩,从而导致害虫受体的衰弱、麻痹直至害虫的瘫痪死亡。
双酰类杀虫剂具有如下优点:对蜜蜂的毒性很低,对水生生物的毒性也很低,在正常的用量下,双酰胺类杀虫剂对非靶标昆虫、对高等动物基本上都是无毒的,防治广谱,几乎对所有的鳞翅目类害虫都有优良的活性。
现在在使用的双虫酰胺类杀虫剂有很多,其中氯虫苯甲酰胺:又名“康宽”,它是在氟苯虫酰胺之后开发出来的第二个双酰胺类杀虫剂。其不仅保留了双酰胺类杀虫原有的优点,更重要的是改变了原来对鱼类及水生生物毒性大的缺点,使得氯虫苯甲酰胺迅速的成为杀虫剂市场的主流品种。但是由于长期性连续性的使用,其抗药性的问题相对其它双酰胺类的品种则显得更加突出。双酰胺类杀虫剂的优点非常突出,但是其缺点也是不容忽视的。根据使用的实际情况来看,在农作物的一个生长周期后其抗性就会明显增加,两年以上的抗性可以达到几十倍。因此,需要研究杀虫效果更优异双酰胺类杀虫剂。
发明内容
本发明提供一种具有优异的杀虫活性的双酰胺杀虫剂,与现有的双酰胺类杀虫剂相比具有使用浓度更低,起效时间更短,持效时间更长的优势。
本发明公开了一种式I 化合物和其盐及立体异构体,
其中,R1选自羟基、硝基、卤代(C1-C6)烷氧基和(C1-C6)烷磺酸基中一种,R2选自卤素和(C1-C6)烷磺酸基中一种。
本发明还提供了一种杀虫剂组合物,其含有本发明的式I 化合物和其盐及立体异构体作为有效成分。
本发明还提供一种防治植物害虫的方法,将本发明化合物或含有本发明化合物的组合物或含有本发明化合物组合物的制剂施用于植物上。
有益效果
本发明的化合物或其盐类不仅具有优异的杀虫效果,同时,与现有的双酰胺类杀虫剂相比具有使用浓度更低,起效时间更快,持效时间更长的优势。
具体实施方式
为使本发明实施例的目的、技术方案和优点更加清楚,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作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。除非另有其它明确表示,否则在整个说明书和权利要求书中,术语“包括”或其变换如“包含”或“包括有”等等将被理解为包括所陈述的成分或步骤,而并未排除其它物质成分或步骤。
另外,为了更好的说明本发明,在下文的具体实施方式中给出了众多的具体细节。
本领域技术人员应当理解,没有某些具体细节,本发明同样可以实施。在一些实施例中,对于本领域技术人员熟知的原料、方法、手段等未作详细描述,以便于凸显本发明的主旨。
本文所用的术语“烷基”(以及在包含烷基的其它基团,例如烷氧基的烷基结构部分,卤代烷基的烷基部分、烷硫基的烷基部分)在每种情况下表示通常具有1-20个碳原子,优选1-6个碳原子(C1-C6),烷基的示例如甲基、乙基、正丙基、异丙基、正丁基、1-甲基丙基(仲丁基)、2-甲基丙基(异丁基)、1,1-二甲基乙基(叔丁基)、正戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、2,2-二甲基丙基、1-乙基丙基、1,1-二甲基丙基、1,2-二甲基丙基、己基、1-甲基戊基、2-甲基戊基、3-甲基戊基、4-甲基戊基、1,1-二甲基丁基、1,2-二甲基丁基、1,3-二甲基丁基、2,2-二甲基丁基、2,3-二甲基丁基、3,3-二甲基丁基、1-乙基丁基、2-乙基丁基、1,1,2-三甲基丙基、1,2,2-三甲基丙基、1-乙基-1-甲基丙基或1-乙基-2-甲基丙基,但不限于此。
本发明“C1-C6烷氧基”示例有:甲氧基,乙氧基,正丙氧基等,但不限于此。
本发明“C1-C6烷磺酸基”示例有:甲磺酸基,乙磺酸基,丙磺酸基等,但不限于此。
本发明的“卤素”是指氟、氯、溴和碘。
本发明首先提供一种式I 化合物和其盐及立体异构体,
其中,R1选自羟基、硝基、卤代(C1-C6)烷氧基和(C1-C6)烷磺酸基中一种,R2选自卤素和(C1-C6)烷磺酸基中一种。
优选地,一些实施方案中,R1独立地选自硝基、氟取代的(C1-C6)烷氧基。
特别优选地,一些实施方案中,R1独立地选自硝基、二氟甲氧基和三氟甲氧基。
优选地,一些实施方案中,R2独立地选自氯、乙基磺酸基。
本发明式I化合物,特别优选下列化合物:
,/>,,/>。
本发明制备式I化合物的方法,可采取如下合成路线:
。
其中式I、式II和式III化合物的合成方法可以参照专利CN101072767A公开的方法制备得到。
本发明还提供一种杀虫剂组合物,本发明的式I 化合物和其盐及立体异构体作为有效成分。
含有本发明的通式I所表示的化合物或其盐类作为有效成分的农业用杀虫剂组合物,适合防除对水稻、果树、蔬菜、其他作物及花卉类 造成灾害的各种农林、园艺、贮粮害虫、卫生害虫或者线虫类等害虫。
所述的害虫包括如下例举的害虫,但不限于此。
绿刺蛾、桥夜蛾、柑橘凤蝶、莎草粘虫、美国白蛾、亚洲玉米螟、东方粘虫、衣蛾、尖翅小卷蛾、大螟、甘薯麦蛾、黄刺蛾、棉铃虫、黄地老虎、甘蔗黄螟、小菜蛾、稻纵卷叶野螟、甜菜夜蛾、二化螟、棉红铃虫、稻绿椿、黑条红椿象、褐圆介壳虫、稻褐蝽、大青叶蝉、二条斑黑尾叶蝉 、苹果木虱、桑木虱、长尾粉蚧、绿盲蝽、甘蓝蚜、大豆蚜、玉米蚜柳 、豆蚜、臭蝽、柑桔木虱 、桔蚜、柑橘粉虱、桃蚜、苹木虱、苹果蚜虫、苹果叶蝉、苹果蚜、合欢双条天牛、绿豆象、甘薯小象、紫苜蓿叶象、稻象甲、稻水象甲、菜豆象、黄星天牛、小猿叶虫、斑喙丽金龟、面粉甲虫、甜菜跳甲、大绿丽金龟、淡色库蚊、甜菜潜叶蝇、南美斑潜蝇、家蝇、稻秆蝇、中华按蚊、白纹伊蚊、三叶斑潜蝇、美洲斑潜蝇、东方果实蝇、蜜柑大实蝇、、南方稻草螽、蝼蛄、小稻蝗、稻蓟马、稻管蓟马、黄蓟马、山楂叶螨、家白蚁、黑胸大蠊、德国小蠊、猫栉头蚤、鸡蚤、草莓芽线虫、水稻干尖线虫、穿刺短体线虫、北方根结线虫、南方根瘤线虫、福寿螺、非洲大蜗牛、番茄潜叶蛾、微小牛蜱、血红扇头蜱、鸡皮刺螨、犬栉头蚤、猫栉头蚤、人蚤、牛血虱、驴血虱、羊虱、阴虱、肺虫、鞭虫、结节虫、绦虫、犬复孔绦虫、多头绦虫、日本血吸虫、疟原虫、肠内肉孢子虫、弓形虫等。但不限于此。
作为本发明的杀虫组合物的任意剂型,可列举出粉剂、颗粒剂、可湿性粉剂、丸剂、片 剂、巨丸剂、胶囊剂、其他含有本发明的化合物的成型品等固体制备物;用于动物皮肤或体腔中的液体制剂(例如,浇泼剂、滴剂);乳剂等水溶性或油性的液体制备物、胶悬剂等混悬状制备物;软膏剂、凝胶等半固体制备物等。固体制备物主要可用于口服给药、或者利用水等进行稀释而用于经皮给药、又或者可用于环境处理。固体制备物可通过将本发明的化合物与适当的赋形剂一起混合而制成 所需的形状,从而进行制备,必要时还可加入辅助剂。作为适当的赋形剂,例如可例示出碳 酸盐、碳酸氢盐、磷酸盐、氧化铝、二氧化硅、黏土、糖、纤维素、经粉碎的谷物、淀粉等。
其中,胶悬剂、乳剂等可直接经皮给药或在稀释后经皮给药,或者在不危害环境的情况 下方便地进行给药。
本发明化合物或组合物适合在动物的皮肤上应用的液体制剂,可通过浇泼、平敷、擦揉、喷雾、散布而进行给药,或者通过浸渍(浸渍、入浴或洗涤)或涂布而进行给药。这些液体制剂可以以与注射用 液体制剂相同的方式进行制备。
将本发明的化合物或组合物外部或内部寄生虫防除剂用作属于人或除人以外的哺乳类或鸟类的动物的药物时,有效成分的最佳量(有效量)会根据治疗或预防的区别、感染寄生虫的种类、 感染的类型和程度、剂型等而改变,但一般而言,在口服给药的情况下,有效成分的最佳量 (有效量)为每天约0.0001至10000mg/kg体重的范围。在非口服给药的情况下,有效成分的最佳量(有效量)为每天约0.0001至10000mg/kg体重的范围,可一次性给药或分次给药。
本发明的外部或内部寄生虫防除剂中的有效成分的浓度通常为0.001~100质量%,优选为0.001~99质量%,进一步优选为0.005~20质量%左右。
本发明的内部寄生虫防除剂可以是直接给药的组合物,也可以是在使用时在稀释成适当浓度后进行使用的高浓度组合物。
此外,为了增强或补充本发明的外部或内部寄生虫防除剂的效果,也可以同时使用现有的内部寄生虫防除剂。同时进行使用时,可以是在给药前混合两种以上的有效成分而得到的制剂,也可以将两种以上的不同的制剂分开进行给药。
由于本发明的化合物对给水田作物、旱田作物、果树、蔬菜、其他作物及花卉等造成灾害的所述害虫具有显著的防除效果,因此通过根据预测产生害虫的时期,在害虫产生前或确认到害虫产生时施用于育苗设施、水 田、旱田、果树、蔬菜、其他作物、花卉等的种子、水田水、茎叶或土壤等栽培载体等,能够发挥本发明的农业园艺用杀虫剂的所期望的效果。
以下将通过实施例对本发明进行详细描述。
以下实施例中,在没有特别说明的情况下,所用原料均采用市售品。
其中,反应物和产物的含量(纯度)通过液相色谱(Agilent HPLC 1260)测得。
反应的转化率和选择性通过以下公式计算:
转化率=(原料投入摩尔量-产物中残留的原料摩尔量)/原料投入摩尔量×100%。
选择性=目标产物的实际摩尔量/目标产物的理论摩尔量×100%
实施例1:3-溴-1-(3-氯吡啶基)-N-(2-甲基-6-(甲基氨基甲酰)-4-硝基苯基)-1H-吡唑-5-甲酰胺的制备(化合物PPN-01)
1.1 2-氨基-5-硝基-N,3-二甲氨基苯甲酰胺的制备
500ml四口瓶中加入0.1mol6-硝基-8-甲基-2H-3,1-苯并噁嗪-2.4(1H)二酮,乙腈100ml,加入乙酸0.12mol,降温至0-5度,开始滴加40%甲胺水溶液0.11mol,保温反应2h,接着加入100ml水,继续搅拌30min后,过滤,得到黄色固体,收率80%。
1.2:5-溴-2-(3-氯-吡啶-2-基)-2H-吡唑-3-甲酸的制备
1.2.1:3.4.5-三溴-1H-吡唑的合成
将34克吡唑溶解在100g水中,并与337 .2g的48%溴化氢溶液一起装入1000ml反应器中。 在2小时内在0℃下滴加170g的30%过氧化氢。反应温度控制在0℃-20℃。反应后,将产物以固体沉淀,然后用10%亚硫酸钠淬灭反应混合物。过滤和干燥后,获得142g高纯度(97%, LC面积)的3 ,4-二溴-1H-吡唑和3 ,4 ,5-三溴-1H-吡唑的混合物(3,4-二溴-1H-吡唑与3,4,5-三溴-1H-吡唑的比率=9:1,LC面积)。
1.2.2:3.5-二溴-1H-吡唑的合成
将100克3 ,4 ,5-三溴-1H-吡唑和3 ,4 ,-二溴-1H-吡唑的混合物(3 ,4-二溴-1H-吡唑与3,4,5-三溴-1H-吡唑的比率=9:1,LC面积)、在500mL水中的111g的Na2SO3在160℃-180℃ 下反应4小时以完成反应。反应完成后,用甲基异丁基酮(MIBK)萃取反应混合物,并在40℃-45℃下真空浓缩,以获得呈固体的3.5-二溴-1H-吡唑。
1.2.3:2-(3.5-二溴-1H-吡唑-1-基)-3-氯吡啶的合成
将11 .5克3-溴-1H-吡唑和14 .7g的40%NaOH溶液在甲苯的存在下在150℃-160℃ 的温度下反应。在回流温度下通过共沸蒸馏去除水,以产生相应的3-溴-1H-吡唑钠盐。然 后,添加甲苯和13 .5g的2 ,3-二氯吡啶并使混合物在150℃-160℃下反应。反应后,用水淬灭 反应混合物,并分离有机层。然后用水洗涤有机层,并在40℃-45℃下真空浓缩,以获得呈固体的2-(3.5-二溴-1H-吡唑-1-基)-3-氯吡啶。
1.2.4:3-溴-1-(3-氯吡啶-2-基)-1H-吡唑-5-甲酸甲脂的合成
将32克2-(3.5-二溴-1H-吡唑-1-基)-3-氯吡啶溶解在THF中,然后在0℃下添加iPr2NMgCl(原位MeMgCl和iPr2NH),以产生相应的2-(3-溴-1H-吡唑-1-基) -3-氯吡啶镁盐。在2 .5小时后,在6小时内在室温下滴加52 .0g的DMC。反应温度控制在20℃-40℃。反应后,在 减压下蒸馏出THF和DMC,并然后用水淬灭反应混合物。接下来,添加甲苯。分离和浓缩后,获 得36 .7g高纯度(90%,LC面积)的3-溴-1-(3-氯吡啶-2-基)-1H-吡唑-5-甲酸甲脂。
1.3:3-溴-1-(3-氯吡啶基)-N-(2-甲基-6-(甲基氨基甲酰)-4-硝基苯基)-1H-吡唑-5-甲酰胺的制备
3-溴-1-(3-氯-2-吡啶基)-1H-吡唑-5-羧酸(95%,0.1mol)和2-氨基-5-硝基-N,3-二甲氨基甲酰胺0.1mol在乙腈溶剂中混合物加入3-甲基吡啶0.3mol,将混合物降温至-5度,开始滴加0.2mol甲磺酸,在该温度下搅拌反应1h,然后,滴加20ml水,冷却至0度,持续1h,过滤混合物,用20ml+10ml水洗涤产物,得到白色化合物,收率60%。
核磁数据表征如下:
1H NMR (500 MHz, DMSO) δ 10.62 (s, 1H , H-1), 8.54 (d, 1H, H-2), 8.49(t, 1H,H-3), 8.27 (d,J= 2.3 Hz, 1H, H-4), 8.18 (dd,J= 8.0, 1.1 Hz, 1H, H-5),8.13 (d,J= 2.4 Hz, 1H, H-6), 7.61(dd,J=4.7 Hz, 1H, H-7), 7.44 (s, 1H, H-8),2.69 (d,J= 4.6 Hz, 3H, H-9), 2.30 (s, 3H, H-10)。
参照上述类似方法合成如表1所示化合物
表1 本发明实施例化合物
生物测定
1试验名称
本发明化合物对甜菜夜蛾毒力测试试验
2试验目的
以95%氯虫苯甲酰胺原药为对照药剂,通过触杀试验,测试本发明合物对甜菜夜蛾毒力测试,为后期最佳配方筛选提供依据。
3试验材料
3.1试验对象的选择
甜菜蛾幼虫
新鲜甘蓝叶片
3.2试验仪器设备
电子分析天平、三角瓶、Φ9cm*5cm透明塑料碗、烧杯、滤纸、剪刀、记号笔等
3.3 试验材料与药品
PPN-01(98%)、PPN-02(98%)、PPN-03(98%)、PPN-04(98%)、95%氯虫苯甲酰胺原药、丙酮(AC)、吐温80、水。
4试验设计
4.1药剂
4.1.1供试药剂制备
(1)1%PPN-01、1%PPN-02、1%PPN-03、1%PPN-04母液制备:用丙酮作溶剂制备。
(2)0.1%氯虫苯甲酰胺母液制备:用丙酮作溶剂制备。
(3)0.5%吐温80溶液制备:用水作溶剂制备,作为乳化剂溶液备用。
(4)供试药剂制备:用母液和0.5%吐温80溶液制备成需要的测试浓度。
4.1.2 药剂用量与处理编号
表2 试验药剂设计
处理组 | 处理编号 | 药剂 | 质量浓度ppm |
1 | P-01-100 | PPN-01 | 100 |
2 | P-01-50 | PPN-01 | 50 |
3 | P-02-100 | PPN-02 | 100 |
4 | P-02-50 | PPN-02 | 50 |
5 | P-03-100 | PPN-03 | 100 |
6 | P-03-50 | PPN-03 | 50 |
7 | P-04-100 | PPN-04 | 100 |
8 | P-04-40 | PPN-04 | 50 |
9 | L-100 | 氯虫苯甲酰胺 | 100 |
10 | L-50 | 氯虫苯甲酰胺 | 50 |
11 | CK | 清水 |
4.2试验方法
4.2.1试验方法
浸虫法。
4.2.2处理组设置
设4个处理,每个处理3个重复,对照清水CK。
4.2.3试虫准备
甜菜夜蛾幼虫。在科云平台购买甜菜夜蛾虫卵,实验室孵化后5d的幼虫。
4.2.4试验处理
在小碗中铺1张湿润滤纸,剪取等面积的甘蓝叶片洗净、晾干放入碗中。试虫用药液浸渍10s,滤纸吸干水分后放在碗中的甘蓝叶片上。每个处理3个重复。每个重复接入10头虫。再用保鲜膜封口,用针刺孔通气。
4.2.5施药时间和观察
2023年7月24日进行处理,1h、2h、6h、12h、24h后观察死虫率。
4.2.6调查方法
Abbott公式:
5实验结果与分析
表3 试验结果
由表3和结果可以看出本发明化合物杀虫效果起效时间快,杀虫效果持效也比较优异。
以上详细描述了本发明的优选实施方式,但是,本发明并不限于此。在本发明的技术构思范围内,可以对本发明的技术方案进行多种简单变型,包括各个技术特征以任何其它的合适方式进行组合,这些简单变型和组合同样应当视为本发明所公开的内容,均属于本发明的保护范围。
Claims (2)
1.式I 化合物和其盐及立体异构体,其特征在于,式I选自下列化合物:
。
2.一种杀虫剂组合物,其特征在于,其含有权利要求1所述式I 化合物和其盐及立体异构体作为有效成分。
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