CN105294596B - 4‑羟基‑3‑苯甲酰基‑2‑烷基‑1,2‑苯并噻嗪‑1,1‑二氧化物衍生物 - Google Patents
4‑羟基‑3‑苯甲酰基‑2‑烷基‑1,2‑苯并噻嗪‑1,1‑二氧化物衍生物 Download PDFInfo
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Classifications
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/02—1,2-Thiazines; Hydrogenated 1,2-thiazines
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
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Abstract
本发明涉及一种4‑羟基‑3‑苯甲酰基‑2‑烷基‑1,2‑苯并噻嗪‑1,1‑二氧化物衍生物,结构通式为(I)。其中:R1代表:C1~C5的烷基;R2代表:2‑NO2,3‑NO2,4‑NO2,2‑Br‑4‑Br,2‑Cl‑3‑Cl,2‑Cl‑5‑Cl,2‑Cl‑4‑F,2‑Cl‑4‑Br,2‑F‑4‑Cl,2‑Br‑4‑F,2‑Br‑4‑Cl,2‑Cl‑4‑NO2,2‑Cl‑4‑CF3,4‑SO2Me。以糖精钠盐为原料,通过亲核反应,Gabriel‑Colman重排,脱羧,烷基化,缩合和Fries重排反应,合成得到了4‑羟基‑3‑苯甲酰基‑2‑烷基‑1,2‑苯并噻嗪‑1,1‑二氧化物类化合物,并且对该类化合物的除草活性进行了测试,其结果显示该类化合物具有较好的除草活性,是一类结构新颖、应用前景广阔的除草剂。
Description
技术领域
本发明涉及一种4-羟基-3-苯甲酰基-2-烷基-1,2-苯并噻嗪-1,1-二氧化物衍生物及应用,特别是4-羟基-3-苯甲酰基-2-烷基-1,2-苯并噻嗪-1,1-二氧化物衍生物在农业上除草方面的用途。
技术背景
4-羟基-3-苯甲酰基-2-烷基-1,2-苯并噻嗪-1,1-二氧化物属于磺酰胺类化合物。磺酰胺是一类非常重要的化合物。自1932年百浪多息被发现具有一定的抗菌作用,并于次年报告用百浪多息治疗由葡萄球菌引起败血症的病例后,随着研究的不断深入,磺酰胺类药物不仅在抗菌方面获得历史性的发展,该类化合物其它的生物活性也相继被发现,如除草活性、杀菌活性和杀虫活性等。近几年对磺胺类化合物的研究与开发越来越受到人们的重视,除已开发的商品化药剂外,报道的许多磺酰胺类衍生物显示了广泛的应用和发展前景。
发明内容
本发明的目的是提供了4-羟基-3-苯甲酰基-2-烷基-1,2-苯并噻嗪-1,1-二氧化物在除草方面的用途。通过以糖精钠盐为原料,通过亲核取代,Gabriel-Colman重排,脱羧,烷基化,缩合反应和Fries重排反应,合成得到了4-羟基-3-苯甲酰基-2-烷基-1,2-苯并噻嗪-1,1- 二氧化物类化合物,并且对该类化合物的除草活性进行了测试,其结果显示该类化合物具有较好的除草活性并且伴有白化现象,是一类结构新颖、应用前景广阔的除草剂。
本发明提供4-羟基-3-苯甲酰基-2-烷基-1,2-苯并噻嗪-1,1-二氧化物的结构通式为(I)。
其中:R1代表:C1~C5的烷基;R2代表:2-NO2,3-NO2,4-NO2,2-Br-4-Br,2-Cl-3-Cl,2-Cl-5-C1,2-Cl-4-F,2-Cl-4-Br,2-F-4-Cl,2-Br-4-F,2-Br-4-Cl,2-Cl-4-NO2,2-Cl-4-CF3, 4-SO2Me。
本发明涉及的化合物的制备方法是通过以糖精钠盐为原料,通过亲核取代,Gabriel-Colman重排,脱羧,烷基化,缩合反应和Fries重排反应,合成得到了4-羟基-3- 苯甲酰基-2-烷基-1,2-苯并噻嗪-1,1-二氧化物类化合物。
本发明涉及的化合物及其可以接受的盐在农业上用作除草剂。
本发明涉及的化合物及其在农业上可以接受的盐还可以作为有效成分与其他成分混合作为农药复合物,用做除草剂。
本发明提供了4-羟基-3-苯甲酰基-2-烷基-1,2-苯并噻嗪-1,1-二氧化物类化合物,并且对该类化合物的除草活性进行了测试,其结果显示该类化合物具有较好的除草活性,是一类结构新颖、应用前景广阔的除草剂。
具体实施方式
实施例1
将20.5g的糖精钠盐溶于200mL N,N-二甲基甲酰胺中,加入10.8g氯乙酸甲酯。反应体系回流搅拌4h,将反应体系加入600mL冰水中,有大量白色固体析出,抽滤,收集白色固体,用冰水洗涤3次,红外干燥,得到23.4g白色固体1。收率91.8%。熔点116~ 117℃。
将12.8g的化合物2溶于200mL甲醇中,加入5.4g的甲醇钠。反应体系回流搅拌4 h,将反应体系加入300mL冰水中,用300mL乙酸乙酯萃取水相2次,合并有机相,用 200mL水洗和饱和食盐水洗涤,再用无水硫酸镁干燥。旋蒸旋干溶剂后,将残余物经过硅胶柱层析分离(石油醚∶乙酸乙酯=9∶1)得到6.4g白色固体2。收率50.0%。熔点173~ 174℃。
将6.4g的化合物2溶于200mL的盐酸中,回流2h。TLC跟踪反应,反应结束后,将反应体系加入600mL冰水中,有白色固体析出。过滤,收集固体,干燥后得到3.2g淡黄色固体3。收率65.3%。熔点157~158℃。
将3.2g的化合物3溶于30mL的N,N-二甲基甲酰胺(DMF)中,依次加入5.3g的碳酸铯,2.3g的碘甲烷,室温搅拌过夜,TLC跟踪反应,反应结束后,将反应体系加入60 mL冰水中,用30mL乙酸乙酯萃取水相2次,合并有机相,用60mL水洗和饱和食盐水洗涤,再用无水硫酸镁干燥。旋蒸旋干溶剂后,将残余物经过硅胶柱层析分离(石油醚∶乙酸乙酯=9∶1)得到2.11g白色固体4。收率62.1%。熔点107-108℃。
将2.11g的化合物4溶于20mL的DMF中,冰浴冷却至0℃,加入0.6g的(60%) NaH,控温0℃搅拌5min。然后加入3.7g的苯甲酰氯,反应体系室温搅拌4h,TLC跟踪反应,反应结束后,将反应体系加入30mL冰水中,用30mL乙酸乙酯萃取水相2次,合并有机相,用20mL水洗和饱和食盐水洗涤,再用无水硫酸镁干燥。旋蒸旋干溶剂后的3.2 g淡黄色固体5,不经分离提纯直接用于下步反应。
将上步制得的3.2g固体5溶入40mL二氯甲烷中,分别加入2.1g的三乙胺,0.5g的氰化钾和0.5g的18-冠-6。反应体系室温搅拌72h之后,加入硫酸亚铁(2.0g)的1mol/L HCl溶液(40mL),搅拌10min。分液,有机相用饱和食盐水洗涤(40mL×2),用无水硫酸镁干燥。硅胶柱层析分离(洗脱剂∶二氯甲烷和1%冰乙酸,v/v),得到1.51g目标化合物I-1,淡黄色固体,收率41.6%。熔点226~228℃;
化合物I-2~I-17按照与I-1相似的方法合成,相关数据列于表1中。
表1
实施例2
用油菜平皿法、稗草小杯法对I-1~I-17化合物进行了除草活性测试。
油菜平皿法:直径6cm的培养皿中铺好一张直径5.6cm的滤纸,加入2mL一定浓度的供试化合物溶液,设置一个只加蒸馏水的空白对照,播种浸种4~6h的油菜种子粒15粒, 30℃下,黑箱培养了66h后测定胚根长度。通过黑暗条件下化合物对油菜胚根的生长抑制来检测化合物的除草活性。
稗草小杯法:通过光照条件下化合物对稗草幼苗株高的生长抑制来检测化合物的除草活性。在50mL的烧杯底部铺满一层大小一致的玻璃球,然后放一张与杯底大小一致的滤纸,加入配置好的一定浓度的待测化合物溶液5.5mL,并设置一个只加蒸馏水的空白对照。播种出芽一致的稗草种子10粒,在28℃的光室内培养60h,测定稗草幼苗地上长度,通过与空白对照计算出对稗草地上部分的抑制率。
化合物I-1~I-17的除草活性列于表2中。
表2化合物I-1~I-17的除草活性
实施例3
苗前盆栽法:塑料盒中装入(11×7.5×6)中装入100g沙土,用水湿润后,播种15颗发芽的种子于泥土下0.5cm深,喷洒待测化合物的溶液(100克/亩),设置一个不喷晒药剂的空白对照。温室下(温度25±1℃,12h光照条件),生长15d。幼苗收割后,从根苗分界处剪切后称重,与空白对照对比,计算抑制百分数。每个浓度设置三个重复,取平均值。
苗后盆栽法:把发芽的种子改成出苗后的种子,其他操作同苗前盆栽法。
化合物I-12,I-13,I-14,I-15I-16的盆栽除草活性列于表3中。
表3目标化合物I-12,I-13,I-14,I-15,I-16的盆栽除草活性
Claims (3)
1.一种4-羟基-3-苯甲酰基-2-烷基-1,2-苯并噻嗪-1,1-二氧化物衍生物,其特征在于其结构通式为(I):
其中:R1代表甲基;
R2代表:2-NO2,3-NO2,4-NO2,2-Br-4-Br,2-Cl-3-Cl,2-Cl-5-Cl,2-Cl-4-F,2-Cl-4-Br,2-F-4-Cl,2-Br-4-F,2-Br-4-Cl,2-Cl-4-NO2,2-Cl-4-CF3,4-SO2Me,2-NO2-4-Cl,2-NO2-4-Br。
2.权利要求1所述的4-羟基-3-苯甲酰基-2-烷基-1,2-苯并噻嗪-1,1-二氧化物衍生物及其可以接受的盐在农业上用作除草剂。
3.权利要求1所述的4-羟基-3-苯甲酰基-2-烷基-1,2-苯并噻嗪-1,1-二氧化物衍生物及其在农业上可以接受的盐作为有效成分与其他成分混合作为农药复合物用做除草剂。
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