CN114656402B - 一种含氟烟酰脲类化合物及其用途 - Google Patents
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
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- 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
Abstract
本发明提供了一种含氟烟酰脲类化合物，结构如通式Ⅰ所示：式中R为：
Description
技术领域 本发明属于农药中杀虫杀螨剂的领域，涉及一种含氟烟酰脲化合物及其作为杀虫杀螨剂的用途，用于农业或林业的害虫害螨的防治。
背景技术 农业上害虫害螨危害农作物的生长，导致减产及品质下降。目前对害虫害螨的防治主要依赖化学农药，由于大量频繁使用杀虫杀螨剂，害虫害螨对其均产生了严重的抗药性，导致用药量越来越大，防效越来越低，持效期缩短，农残升高等一系列问题。新的不同作用机制的杀虫杀螨剂的开发及应用，是解决有害生物抗性的有效手段。氟啶虫酰胺是一种新型含氟吡啶酰胺类昆虫生长调节剂，它可以通过阻碍害虫吮吸作用进行杀虫，对蚜虫及小菜蛾等有良好的防治作用。
本发明化合物与上述氟啶虫酰胺在结构上都含有三氟甲基吡啶环，但在现有技术中如本发明所述的通式Ⅰ化合物及其用作农业杀虫杀螨剂未见公开。
发明内容 本发明的目的在于提供一种结构新颖，合成方法简便、安全高效的杀虫杀螨剂，它可用于农业或林业害虫害螨的防治。
本发明的技术方案如下：
一种含氟烟酰脲类化合物，结构如通式Ⅰ所示：
式中R为：
本发明通式Ⅰ化合物可由如下方法制备：
式中R同上。
4-三氟甲基-3-吡啶甲酰基异氰酸酯与胺类化合物反应生成通式Ⅰ化合物，具体制备方法见本发明合成实施例。表1列出了通式Ⅰ化合物的结构与外观。
表1通式Ⅰ化合物结构及外观
本发明的优点和积极效果：
本发明化合物(通式Ⅰ)作为农业杀虫杀螨剂，具有结构新颖、制备简便、虫螨兼治的优点。本发明化合物对小菜蛾及朱砂叶螨抑杀效果显著，可以达到对农林业害虫害螨兼治的优异效果。本发明化合物对小菜蛾有优良杀灭活性，除Ⅰ-6外在100mg/L浓度下均达到100％；其中Ⅰ-1、Ⅰ-3、Ⅰ-4对小菜蛾的杀灭效果优异，在50mg/L浓度下杀灭率达到100％，特别是Ⅰ-3杀灭效果突出，在20mg/L浓度下杀灭率达到80％以上。本发明化合物对朱砂叶螨有优异抑杀效果，在100mg/L浓度下均达到100％；其中I-1、I-2、I-3、I-4在10mg/L低浓度下达到100％，对朱砂叶螨杀灭效果优于商品化的嘧螨酯，特别是Ⅰ-3、I-4杀灭效果突出，在1mg/L超低浓度下达100％。本发明化合物为含氟吡啶酰脲类化合物，具有生物活性高、对有益生物低毒性、易降解、环境相容性好的特点，特别适用于目前普遍存在的抗药性农业害虫害螨的治理，作为兼具杀虫杀螨农药新品种具有很好的开发及应用前景。
本发明化合物在于防治农业害虫或者螨害，可单独使用，也可与其它活性物质组合使用，以提高产品的综合性能。
本发明还包括以通式Ⅰ化合物为活性组分的杀虫杀螨组合物，其中活性组分在组合物的重量百分含量为1～99％。该杀虫杀螨组合物还包括农业或林业上可接受的载体。
应该明确的是，在本发明的权利要求的限定范围内，可进行各种变动或改动。
具体实施方式
下列合成实例、生测试验结果可用来进一步说明本发明，但不意味着限制本发明。
合成实例
实例1、化合物Ⅰ-2的制备：
(1)中间体4-三氟甲基烟碱酰异氰酸酯的合成：
向装有搅拌磁子的250mL单口烧瓶中加入100g 1,2-二氯乙烷作溶剂，再加入25.4g(0.20mol)草酰氯，加热搅拌均匀，加装干燥管及碱吸收装置。称取4-三氟甲基烟酰胺19.0g(0.10mol)，搅拌下分批次加入至烧瓶中。加毕，升温至回流。TLC(展开剂V(石油醚):V(乙酸乙酯)＝1:2)监测反应，回流3h后，待原料4-三氟甲基烟酰胺完全反应完后，降至室温。减压蒸馏除去溶剂及未反应完全的草酰氯，得浅棕色透明液体，加入20g乙腈配置成48.5g含量为38.1％的4-三氟甲基烟碱酰异氰酸酯-乙腈溶液，密封于样品瓶中冷藏备用。
(2)化合物Ⅰ-2的合成：
向装有搅拌磁子的100mL三口烧瓶中加入20g乙腈作溶剂，再加入3.11g(0.0095mol)2,5-二氯-4-(1,1,2,3,3,3-六氟丙氧基)苯胺，搅拌均匀。将烧瓶内溶液加热至60℃，向其中缓慢滴加5.67g上步配制成的4-三氟甲基烟碱酰异氰酸酯乙腈溶液(4-三氟甲基烟碱酰异氰酸酯量为0.10mol)。滴加完毕后，继续加热至回流，TLC(展开剂V(石油醚):V(乙酸乙酯)＝7:1)监测反应进度。待加热回流反应1h后，TLC检测反应体系中2,5-二氯-4-(1,1,2,3,3,3-六氟丙氧基)苯胺反应完毕后降至室温。向烧瓶中缓慢添加50mL去离子水，烧瓶中出现大量白色固体。继续搅拌15min。抽滤，用去离子水洗涤滤饼三次，烘干，得白色粉末状固体4.19g。柱色谱层析得白色固体。
用类似方法可制得其它目标化合物。
本发明通式Ⅰ中的化合物核磁数据如下：
化合物Ⅰ-1：1H NMR(400MHz,Chloroform-d)δ：10.46(s,1H),9.70(s,1H),8.84(s,1H),8.77(d,J＝5.1Hz,1H),7.50(d,J＝5.1Hz,1H),7.16(t,J＝7.5Hz,1H),7.07(ddd,J＝7.3,5.9,1.7Hz,2H),2.57(q,J＝7.6Hz,2H),2.17(s,3H),1.16(t,J＝7.6Hz,3H)。
化合物Ⅰ-2:1H NMR(400MHz,Chloroform-d)δ：11.93(s,1H),10.94(s,1H),9.07(s,1H),9.01(d,J＝5.1Hz,1H),8.53(s,1H),7.91(q,J＝3.5,2.2Hz,1H),7.74(dd,J＝11.8,5.1Hz,1H),6.50(dq,J＝41.4,5.7Hz,1H)。
化合物Ⅰ-3：1H NMR(400MHz,Chloroform-d)δ：11.71(s,1H),10.42(s,1H),9.05(s,1H),9.01(d,J＝5.2Hz,1H),8.25(d,J＝8.7Hz,1H),7.92(d,J＝5.2Hz,1H),7.58–7.51(m,2H),2.39(s,3H)。
化合物Ⅰ-4：1H NMR(400MHz,Chloroform-d)δ：10.30(s,1H),10.06(s,1H),8.94(s,1H),8.85(d,J＝5.2Hz,1H),7.74(d,J＝2.1Hz,1H),7.60(d,J＝5.2Hz,1H),7.46(s,1H),2.39(s,3H)。
化合物Ⅰ-5：1H NMR(400MHz,Chloroform-d)δ：11.18(s,1H),8.96(s,1H),8.95(s,1H),7.87(d,J＝5.2Hz,1H),7.33(d,J＝8.1Hz,2H),7.18(d,J＝8.1Hz,2H),6.97–6.93(m,2H),6.92–6.88(m,2H),4.39(d,J＝6.0Hz,2H),2.28(s,3H)。
化合物Ⅰ-6：1H NMR(400MHz,Chloroform-d)δ：10.78(s,1H),8.91(s,1H),8.90(d,J＝5.1Hz,1H),8.68(t,J＝5.9Hz,1H),7.60(d,J＝5.2Hz,1H),7.43–7.25(m,2H),7.20–7.12(m,2H),4.32(d,J＝5.8Hz,2H),1.32(s,9H)。
生物活性测试
实例2、杀虫活性测定
(1)杀小菜蛾活性测定方法
具体实施方法如下：供测样品均为化合物与DMF配制成浓度为500mg/L的混合药液，再使用0.1％的吐温-80稀释成为不同浓度梯度的药液。将甘蓝叶片截取为大小形态均匀的圆片，浸润至配制成的梯度浓度的药液中15-20s后取出，每个浓度重复三次，晾干后将叶片置于培养皿内湿润的滤纸上。取30只成长状态相同的小菜蛾幼虫置于培养皿中，培养皿内温度控制于25℃，相对湿度控制于60％，光周期控制于L:D＝16:8，观察记录小菜蛾生长状态。培养时间为72h时，统计小菜蛾幼虫死亡数，结果为三组实验平均值。
表2通式Ⅰ化合物的杀小菜蛾活性测试结果
测试结果表明，本发明化合物对小菜蛾有优良杀灭活性，除Ⅰ-6外在100mg/L浓度下均达到100％；其中Ⅰ-1、Ⅰ-3、Ⅰ-4对小菜蛾的杀灭效果优异，在50mg/L浓度下杀灭率达到100％，特别是Ⅰ-3对小菜蛾的杀灭效果突出，在20mg/L浓度下杀灭率达到82％。
实例3、杀螨活性测定方法
对化合物进行杀螨活性测试，测试方法为喷雾法，测试所选用的对象为朱砂叶螨，具体操作方法为：
将配制成的500mg/L的药液使用0.1％的吐温-80稀释成不同浓度的待测样品，加入至Potter喷雾塔中，压力设置为1.47×105MPa。在直径5cm的圆形蚕豆叶片上接入30头成螨，每个浓度设置三组。再将接有成螨的叶片置于Potter喷雾塔中，喷洒1mL药液，喷雾处理后置于25℃恒温培养箱中培养48h，观察记录朱砂叶螨死亡数，按公式计算螨虫死亡率。
表3通式Ⅰ化合物的杀螨活性测试结果
测试结果表明，本发明化合物对朱砂叶螨有优良抑杀效果，在100mg/L浓度下均达到100％；其中I-1、I-2、I-3、I-4在10mg/L低浓度下达到100％，特别是Ⅰ-3、I-4对朱砂叶螨杀灭效果突出，抑杀效果良好，在1mg/L超低浓度下达100％。本发明化合物除I-5、I-6外，对朱砂叶螨杀灭效果优于嘧螨酯。
Claims (3)
1.一种含氟烟酰脲类化合物，结构如通式Ⅰ所示：
2.根据权利要求1所述的一种含氟烟酰脲类化合物的用途，其特征在于通式I化合物用作农业或林业杀虫杀螨剂，对农业害虫害螨有防治效果。
3.一种杀虫杀螨组合物，含有权利要求1所述的通式Ⅰ化合物为活性组分和农业或林业上可接受的载体。
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