CN116655541A - 一种含氟嘧啶胺类化合物及其用途 - Google Patents
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- -1 pyrimidine amine compound Chemical class 0.000 title abstract description 9
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title abstract description 8
- 229910052731 fluorine Inorganic materials 0.000 title abstract description 8
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- BWAFLSFSMHXWMF-UHFFFAOYSA-N 4-chloro-4,4-difluoro-3-oxobutanoic acid Chemical compound OC(=O)CC(=O)C(F)(F)Cl BWAFLSFSMHXWMF-UHFFFAOYSA-N 0.000 description 1
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- XPOLVIIHTDKJRY-UHFFFAOYSA-N acetic acid;methanimidamide Chemical compound NC=N.CC(O)=O XPOLVIIHTDKJRY-UHFFFAOYSA-N 0.000 description 1
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- CBDPWKVOPADMJC-UHFFFAOYSA-N ethyl 4,4-difluoro-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)C(F)F CBDPWKVOPADMJC-UHFFFAOYSA-N 0.000 description 1
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- CIFWZNRJIBNXRE-UHFFFAOYSA-N mepanipyrim Chemical compound CC#CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 CIFWZNRJIBNXRE-UHFFFAOYSA-N 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
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- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- YFGYUFNIOHWBOB-UHFFFAOYSA-N pirimicarb Chemical compound CN(C)C(=O)OC1=NC(N(C)C)=NC(C)=C1C YFGYUFNIOHWBOB-UHFFFAOYSA-N 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P7/00—Arthropodicides
- A01P7/02—Acaricides
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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
- C07D401/02—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 containing two hetero rings
- C07D401/12—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 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Environmental Sciences (AREA)
- Wood Science & Technology (AREA)
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- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Insects & Arthropods (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
本发明公开了一种含氟嘧啶胺类化合物，结构如通式I所示：其中Ar为：
Description
技术领域 本发明属于农药中杀螨剂领域，涉及一种含氟嘧啶胺类化合物及其用途。
背景技术 螨虫是一种农林业常见的害虫，危害蔬菜、棉花、果树等作物，造成粮食减产，对作物生长有巨大损害。因此，发明绿色低毒、高效、低残留、药效时间长的农药杀螨剂意义重大。螨虫具有体积小、繁殖快、适应性强、易产生抗药性等特点，是公认的难防治的有害生物群落。由于农业害螨容易产生抗药性，一些商品化杀螨剂因抗药性失去原有的高效性，逐渐不能满足现代农业对杀螨剂超高效、长持效及低公害的要求，需要不断进行高效杀螨剂新品种的研发。在农药领域，嘧啶类化合物具有杀虫、杀螨、杀菌、除草、植物生长调节等活性，如嘧啶类杀虫剂丁嘧硫磷(Tebupirimfos)、抗芽威(Pirimicarb)、嘧虫胺(Flufenerim)等，商品化的嘧啶类杀菌剂有嘧菌胺(Mepanioyrim)、氟嘧菌胺(Dflumetorim)、甲基嘧菌胺(yrimethanil)、环丙嘧菌胺(Cyprodinil)。在现有技术中，如本发明涉及的一种含氟嘧啶胺类化合物及其用作杀螨剂的应用未见公开。
发明内容 本发明的目的是提供一种结构新颖、使用安全、高效低毒的含氟嘧啶胺类化合物，其用作农作物杀螨剂，可用于农业或林业害螨的防治。
本发明的技术方案如下：
一种含氟嘧啶胺类化合物，结构如通式I所示：
其中Ar为：/>
本发明通式Ⅰ化合物可由如下反应制备：
式中Ar同上，具体制备方法见本发明实施例。
表1列出了通式Ⅰ化合物的结构和物理性质。
表1化合物Ⅰ的结构和物理性质
本发明的优点和积极效果：
本发明含氟嘧啶胺类化合物，不仅结构新颖，而且有优异的杀螨活性(见表2)，药效显著高于对照的商品化特效杀螨剂炔螨特，特别适用于目前普遍存在的抗药性农业害虫害螨的治理，能够更好的应对螨虫抗药性问题。本发明化合物为氮杂环类化合物，具有生物降解性好、残留低、环境相容性好的优点。本发明化合物合成工艺简单、原料易得、中间体不需要精制、防治成本低、高效低毒，具有作为农用杀螨剂新品种的前景和商品化潜力。
本发明化合物用于防制作物螨害用途时，根据需要可以单独使用，也可以与其它杀虫杀螨剂等组合使用，以提高产品的综合功能。
本发明还包括以通式Ⅰ化合物作为活性组分的杀虫杀螨组合物，该组合物中还包括农业或林业上可以接受的载体。
本发明的组合物可以制剂的形式施用，通式Ⅰ化合物作为活性组分溶解或分散于载体或溶剂中，添加适当的表面活性剂配制成乳油、悬浮剂、微乳剂等。
应该明确的是，本发明权利要求所限定的范围内，可进行各种变换和改动。
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、式Ⅰa化合物的制备：
(1)2-氯-4,4-二氟乙酰乙酸乙酯的合成
将4,4-二氟乙酰乙酸乙酯(16.6g，0.1mol)、二氯甲烷60mL加入到250mL三口瓶中，在冰浴条件下缓慢滴加二氯亚砜(14.28g，0.12mol)，滴加完毕转移至25℃条件下反应12h，薄层色谱跟踪检测反应完成，减压蒸馏除去二氯甲烷和多余的二氯亚砜，得到白色油状物，产率89％。
(2)5-氯-6-二氟甲基嘧啶-4-醇的合成
将醋酸甲脒(10.4g，0.1mol)、甲醇钠(36g，0.2mol)、甲醇60mL加入到250mL三口瓶中，在冰浴条件下搅拌30min将醋酸游离出来，缓慢滴加2氯-4,4-二氟乙酰乙酸乙酯(20.0g，0.1mol)反应24h，薄层色谱跟踪检测反应完成，加入盐酸(20.0g，0.2mol)调节pH至酸性，不断搅拌使产物完全析出，减压抽滤，得到白色固体，烘干，产率72％。
(3)4,5-二氯-6-二氟甲基嘧啶的合成
将5-氯-6-二氟甲基嘧啶-4-醇(18.0g，0.1mol)、二氯亚砜50mL加入到250mL单口瓶中，滴加三滴DMF催化，回流反应4h，薄层色谱跟踪检测反应完成，减压蒸馏除去多余的二氯亚砜，得到红棕色油状物，产率94％。
(4)化合物Ⅰa的合成
将4,5-二氯-6-二氟甲基嘧啶(1.98g，0.01mol)、4-对甲苯氧基苄胺(2.13g，0.01mol)、碳酸钾(1.656g，0.012mol)、DMF30 mL加入到100mL三口瓶中，逐渐升温至80℃，反应3h，薄层色谱跟踪检测反应完成，降温至室温，缓慢加入25mL水，不断搅拌使产物充分析出，减压抽滤，得到白色固体，粗产物经柱层析(石油醚：乙酸乙酯＝12：1)纯化，得到目标化合物Ⅰa。
Ⅰb的制备方法与Ⅰa类似。
Ⅰa的1H NMR(500MHz,DMSO-d6)δ8.50(s,1H),8.47(d,J＝7.0Hz,1H),7.32(d,J＝8.1Hz,2H),7.18(d,J＝8.5Hz,2H),7.07(s,1H),6.98–6.91(m,2H),6.89(d,J＝8.5Hz,2H),4.64(d,J＝6.1Hz,2H),2.29(s,3H)；13C NMR(126MHz,DMSO-d6)δ157.80,156.45,155.36,154.53,134.24,132.63,132.61,129.90,128.82,118.19,115.67,112.35,109.20,107.42,105.56,45.80,20.49.
Ⅰb的1H NMR(500MHz,DMSO-d6)δ8.52(d,J＝16.5Hz,2H),8.40(d,J＝2.5Hz,1H),7.80(dd,J＝8.2,2.5Hz,1H),7.49–7.42(m,1H),7.06(t,J＝53.1Hz,1H),4.67(d,J＝6.1Hz,2H)；13C NMR(126MHz,DMSO-d6)δ157.85,155.61,153.90,150.33,149.25,136.06,132.68,122.46,110.19,107.54,46.12.
生物活性测试
实例2、杀螨活性测试
杀螨测试方法：以朱砂叶螨(Tetranychus cinnabarinus)为测试对象，采用喷雾法。将试验化合物用DMF溶解，配制成浓度为200mg/L的药液，然后用含10％ TW-20的水稀释至所需浓度(100mg/L、10mg/L)。取2片真叶菜豆苗，接种朱砂叶螨成螨数量为30头，用手持喷雾器进行整株喷雾处理，然后放入标准观察室，48h观察记录螨虫的死亡情况。以炔螨特(Propargite)为阳性对照，清水空白对照，每组试验药液设3次重复试验，1次空白试验，并计算朱砂叶螨的致死率。
致死率(％)＝(药剂处理死亡率-空白对照死亡率)/(1-空白对照死亡率)×100％
表2对朱砂叶螨的杀螨活性测试结果
由表2数据可见，本发明式Ⅰ化合物有优异的杀螨活性，在相同浓度下对朱砂叶螨成螨的杀螨活性显著优于常用的特效杀螨剂炔螨特。
Claims (3)
1.一种含氟嘧啶胺类化合物，结构如通式I所示：
其中Ar为：/>
2.根据权利要求1所述的一种含氟嘧啶胺类化合物的用途，其特征在于通式Ⅰ化合物用作农业或林业杀螨剂，防治农林业上害螨。
3.一种杀螨剂组合物，含有权利要求1所述的通式I化合物为活性组分和农业、林业上可接受的载体。
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| CN114516841A (zh) * | 2020-11-20 | 2022-05-20 | 湖南海利常德农药化工有限公司 | N-芳氧/硫苄基二氟甲基嘧啶胺类化合物及其制备方法与应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114516841A (zh) * | 2020-11-20 | 2022-05-20 | 湖南海利常德农药化工有限公司 | N-芳氧/硫苄基二氟甲基嘧啶胺类化合物及其制备方法与应用 |
| CN114516841B (zh) * | 2020-11-20 | 2024-02-27 | 湖南海利常德农药化工有限公司 | N-芳氧/硫苄基二氟甲基嘧啶胺类化合物及其制备方法与应用 |
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