CN116589414A - 一种含氟苯基喹唑啉类化合物及其用途 - Google Patents
一种含氟苯基喹唑啉类化合物及其用途 Download PDFInfo
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- -1 phenyl quinazoline compound Chemical class 0.000 title claims abstract description 19
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- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 9
- 239000011737 fluorine Substances 0.000 title claims abstract description 9
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- HVFQJWGYVXKLTE-UHFFFAOYSA-N 3,5-bis(trifluoromethyl)benzoic acid Chemical compound OC(=O)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 HVFQJWGYVXKLTE-UHFFFAOYSA-N 0.000 description 1
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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
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/94—Nitrogen atoms
-
- 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
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- 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
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Abstract
本发明提供了一种含氟苯基喹唑啉类化合物,结构如通式Ⅰ所示:,式中R1为:
Description
技术领域 本发明属于农用杀螨剂领域,涉及一种含氟苯基喹唑啉类化合物及其用途。
背景技术 农业上病虫害导致作物减产及品质下降,目前其防治技术主要依赖化学农药。喹唑啉类化合物具有生物活性,在抗病毒、杀虫、杀螨、抑菌、除草等方面均有应用。例如,化合物1能抑制玉米大斑病菌;化合物2,商品名氟喹唑,用作农用杀菌剂,用于防治小麦、水稻、甜菜、油菜、豆科作物、葡萄和苹果等的菌害;化合物3,商品名喹螨醚,用作农业杀螨剂。
本发明合成了一种含氟苯基喹唑啉类化合物,在现有技术中,如本发明所述的通式I化合物及其用作农林业杀螨剂未见公开。
发明内容 本发明的目的在于提供一种结构新颖、高效、安全的杀螨剂,它可用于农业常见的螨害的有效防治。
本发明的技术方案如下:
本发明提供了一种含氟苯基喹唑啉类化合物,结构如通式Ⅰ所示:
式中R1为:/>
本发明通式Ⅰ化合物可由如下方法制备,反应式中各基团定义同前。
通式Ⅰ化合物及其中间体的具体制法见本发明合成实例。
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:
本发明将喹唑啉结构与三氟甲基氟苯结构相结合,设计并制备了一种结构新颖的2-苯基喹唑啉氨(醚)类化合物,含氟基团增加了脂溶性和渗透性,显著提高了其内吸传导作用,从而提高了其药效,具有优异的杀螨活性,可以有效防止害螨。本发明化合物合成原料易得,合成工艺简单,无需高温高压和特殊设备,生产中产生“三废”少,收率较高,生产成本低。本发明化合物为氮杂环类氨(醚)类化合物,生物降解性好,环境污染小,是具有良好产业化前景的新型环保型杀螨剂,具有作为创制性杀螨剂新品种产业化的前景和商品化的潜力。
本发明式I化合物及其盐在防治有害螨时,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、微乳剂或可湿性粉剂等。
应该明确的是,在本发明的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
下列合成实例及生测结果可用来进一步说明本发明,但并不意味着限制本发明。
合成实例:
实例1.化合物Ⅰa的制备:
(1)3,5-双三氟甲基苯甲酰氯的合成
取25.8g(0.1mol)3,5-双三氟甲基苯甲酸加入100mL单口烧瓶中,在室温下加入50mL二氯乙烷作溶剂,然后再加入20mL氯化亚砜,在回流状态下反应5h,待反应完毕后,60℃减压蒸馏,除去多余的溶剂和未反应的氯化亚砜,得到棕色液体3,5-双三氟甲基苯甲酰氯。
(2)邻氨基苯甲酰胺的合成
将15.7g(0.1mol)靛红酸酐加入到500mL三口烧瓶中,然后加入100mL水作溶剂,室温搅拌下缓慢滴加21.87g(0.5mol)80%的氨水,在滴加过程中放出大量热,控制滴加速度使温度不超过40℃,在反应液中固体逐渐溶解,而后又慢慢析出大量固体,反应3~4h后,TLC监测反应完毕,抽滤,固体用清水洗涤两次,除去残留的氨水,烘干,得到灰色固体,收率81%。
(3)N-(2-氨基甲酰基苯基)-3,5-双三氟甲基苯甲酰胺的合成
向500mL三口烧瓶中加入27.7g(0.1mol)3,5-双三氟甲基苯甲酰氯,然后加入200mL乙腈作溶剂,室温搅拌下加入13.6g(0.1mol)邻氨基苯甲酰胺和13.8g(0.1mol)无水碳酸钾,控制温度保持45℃左右反应5h,期间产生大量固体,TLC监测反应完毕后将反应液减压蒸馏,得到的固体用水洗涤,抽滤,得到该中间体N-(2-氨基甲酰基苯基)-3,5-双三氟甲基苯甲酰胺。
(4)中间体2-(3,5-双三氟甲基苯基)喹唑啉-4(3H)酮的合成
称取37.6g(0.1mol)N-(2-氨基甲酰基苯基)-3,5-双三氟甲基苯甲酰胺于250mL三口烧瓶中,加入100g乙醇作溶剂,继续加入6g(0.15mol)NaOH,升温至回流,反应4h,TLC监测反应完毕,将反应液倒入1L冰水中,随后向溶液中滴加稀盐酸,滴加过程中不断析出固体,用pH试纸检测溶液呈弱酸性后停止滴加,抽滤,用清水洗涤滤饼三次,烘干,得到白色固体产物2-(3,5-双三氟甲基苯基)喹唑啉-4(3H)酮。
(5)中间体4-氯-2-(3,5-双三氟甲基苯基)喹唑啉的合成
取35.8g(0.1mol)2-(3,5-双三氟甲基苯基)喹唑啉-4(3H)酮于500mL三口烧瓶中,加入200g二氧六环作溶剂,再加入15.3g(0.1mol)三氯氧磷,升温至回流,随着反应的进行,固体逐渐溶解,反应12h后,TLC监测反应完毕,经过减压蒸馏除去多余的二氧六环与三氯氧磷。加水,用乙酸乙酯萃取两次,分液,有机相减压蒸馏,得到棕色固体产物4-氯-2-(3,5-双三氟甲基苯基)喹唑啉。
(6)化合物Ⅰa的合成
在干燥的100mL三口烧瓶中,首先加入3.77g(0.01mol)4-氯-2-(3,5-双三氟甲基苯基)喹唑啉,再加入20mL乙腈作为溶剂,再加入1.66g(0.012mol)无水碳酸钾作缚酸剂,最后加入异丙胺0.012mol,控制温度40℃反应2~3h,TLC监测显示完全反应,将反应液冷却至室温,加入50mL水,用50mL乙酸乙酯萃取2次,合并有机相,减压蒸馏,粗品经过柱层析进行纯化,得到目标化合物Ⅰa,收率91%。
其他目标化合物Ⅰb~Ⅰe与Ⅰa的制备相似。
目标化合物的核磁数据:
Ⅰa:1H NMR(500MHz,DMSO-d6)δ(ppm):8.90(d,2H),8.30(d,J=8.3Hz,1H),8.13–8.07(m,2H),7.73(d,J=4.0Hz,2H),7.47(m,J=8.6,4.3Hz,1H),4.57(m,J=6.6Hz,1H),1.33(d,J=6.4Hz,6H)。13C NMR(101MHz,DMSO-d6)δ(ppm):159.46,156.48,149.83,141.67,133.26,130.99,130.66,130.34,128.34,128.02,127.98,126.32,125.20,123.47,122.49,114.58,42.99,22.18。
Ⅰb:1H NMR(500MHz,DMSO-d6)δ(ppm):8.94(d,2H),8.54(t,J=5.5Hz,1H),8.25(d,J=8.2Hz,1H),8.18(s,1H),7.78(t,J=3.3Hz,2H),7.52(m,J=8.2,5.7,2.5Hz,1H),3.58(q,J=6.9,6.4Hz,2H),1.74(m,J=7.6Hz,2H),0.98(t,J=7.4Hz,3H)。13C NMR(101MHz,DMSO-d6)δ(ppm):160.31,156.50,149.81,141.62,133.42,131.40,131.07,130.75,128.44,128.06,128.02,126.59,125.22,123.23,122.51,114.65,43.04,22.11,12.00。
Ⅰc:1H NMR(500MHz,DMSO-d6)δ(ppm):8.97(d,J=14.6Hz,2H),8.62(s,1H),8.30(d,J=8.5Hz,1H),8.24(t,1H),7.82(m,J=17.0,9.0Hz,2H),7.58–7.47(m,1H),3.88–3.76(t,2H),3.71–3.64(m,2H),3.34(s,3H)。13C NMR(101MHz,DMSO-d6)δ(ppm):160.36,156.41,149.79,141.52,133.46,131.04,130.90,130.72,130.39,128.44,126.64,125.21,123.27,122.50,114.62,114.23,70.16,58.37,40.78。
Ⅰd:1H NMR(500MHz,DMSO-d6)δ(ppm):8.96(d,J=12.0Hz,2H),8.30(d,J=8.1Hz,1H),8.19–8.10(m,1H),8.04(m,J=6.8,4.9Hz,2H),7.74(d,J=8.4Hz,1H),6.75–6.48(m,1H),5.16–4.94(m,2H)。
Ⅰe:1H NMR(500MHz,DMSO-d6)δ(ppm):8.81(dd,2H),8.16(d,J=9.4Hz,1H),8.11–8.02(m,1H),7.91(m,J=16.8,8.3Hz,2H),7.65(t,J=7.4Hz,1H),6.87(m,J=51.8,5.3Hz,1H),5.18(d,J=13.6Hz,2H)。
生物活性测定:
实例2、式Ⅰ化合物杀二斑叶螨生物活性测试
对上述所合成的10个新化合物Ⅱ-5a~Ⅱ-5j进行杀螨生物活性测试,本试验参照NY/T1154.9-2008《农药室内生物测定试验准则杀虫剂》第9部分:喷雾法进行[94]。具体方法如下:按照试验设计将药剂配制成为系列浓度的稀释液,以0.1%吐温-80水为对照;取长势一致的辣椒苗盆栽,每株辣椒苗上接100头二斑叶螨成螨,在茎部涂抹凡士林,防止成螨逃逸;置于养虫室培养24h后,检查原始虫数,并放入养虫室培养。每个浓度3次重复。置于(26±1)℃、相对湿度70%~80%、光照16h:8h(L:D)条件下正常饲养。药前记录总虫数,药后24h、48h、72h记录残留二斑叶螨成螨数,计算死亡率和异常率。
死亡率(%)=死亡虫数/处理总虫数×100
异常率(%)=(生命活动异常数+死亡虫数)/处理总虫数×100
表2式Ⅰ化合物对二斑叶螨活性测试结果
由表2试验数据可见,式Ⅰ化合物对二斑叶螨有优良的杀灭活性,在250mg/L的施药浓度条件下,化合物Ⅰa、Ⅰc、Ⅰd、Ⅰe的杀灭率都能达到90%以上,其中Ⅰe能够高达100%;在100mg/L的施药浓度条件下,化合物Ⅰd达到90%以上,Ⅰe达到96%以上。
Claims (3)
1.一种含氟苯基喹唑啉类化合物,结构如通式Ⅰ所示:
式中R1为:/>
2.根据权利要求1所述的一种含氟苯基喹唑啉类化合物的用途,其特征在于通式I化合物用作农业或林业杀螨剂,对农林业害螨有防治效果。
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或林业上可接受的载体。
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