CN117486766A - 一种酰胺类杀菌剂化合物及其应用 - Google Patents
一种酰胺类杀菌剂化合物及其应用 Download PDFInfo
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- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
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Abstract
本发明公开一种式I化合物及其立体异构体和其盐,I,其中,R选自H、卤素、C1‑C4烷基和C1‑C4卤代烷基。本发明化合物具有较优异的杀菌效果。
Description
技术领域
本发明属于农用杀菌剂领域,具体涉及一种结构新颖的酰胺类杀菌剂。本发明还涉及含有本发明化合物的组合物及其应用。
背景技术
酰胺类杀菌剂是一类效低毒的新型类杀菌剂,具有药效好,防治时间长,能水稻提高结实率的特点。该类杀菌剂具有强内吸传导及长持效性,其对由半知菌、担子菌引起的如纹枯病、黑粉病、立枯病等具有较为良好的防效。酰胺类杀菌剂一般是通过抑制病原真菌体内线粒体呼吸链复合酶II(琥珀酸-泛醌氧化还原酶,succinate-ubiquinoneoxidoreductase)的活性,从而使电子无法从琥珀酸转移至泛醌,造成菌体ATP无法正常合成,最终导致菌体因能量匮乏而死亡。
目前酰胺类杀菌剂已经成为研究开发的热点。不断有毒性更小、对环境更安全酰胺类化合物被研究开发出来。
发明内容
本发明公开了一种新型的酰胺类化合物其具有优异的杀菌、活性,可用于农作物的杀菌剂。
具体的,本发明公开了一种式I 化合物及其立体异构体和其盐,
I,
其中,R选自H、卤素、C1-C4烷基和C1-C4卤代烷基。
本发明还提供一种制备式I 化合物及其立体异构体和其盐的方法,其包括式II和酰酰化试剂反应后得到的酰化产物与式III化合物进行反应制备得到式I化合物,其合成路线如下:
,其中,选自H、卤素、C1-C4烷基和C1-C4卤代烷基。
本发明还公开了一种组合物,所述组合物含有本发明的化合物。
本发明的化合物或本发明组合物在防治植物病害中具有较好的应用。
有益效果
本发明化合物相对现有的酰胺类化合物表现出更加优异的杀菌效果。
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。
当本发明的化合物能以互变异构体的形式存在时,在适用时,上文和下文中的所
述化合物应理解为也包括相应的互变异构形式,即使这些互变异构形式未在每种情况中明确提及。
若本发明所述式I化合物具有可以被离子化的官能团,则它们还可以以其农用盐或其混合物形式使用。
本发明中卤素通常是氟、氯、溴或碘,优选氟、溴或氯。相应地,这也适用于与其它结构结合的卤素,比如卤代烷基。卤代烷基优选具有 1 到 6 个碳原子的链长,更优选具有1 到4个碳原子的链长。C1-C4卤代烷基示例,例如氟甲基、二氟甲基、三氟甲基、氯甲基、二氯甲基、三氯甲基、2,2,2-三氟乙基、2-氟乙基、2-氯乙基、五氟乙基、1,1-二氟-2,2,2-三氯乙基、2,2,3,3-四氟乙基和2,2,2-三氯乙基;优选氟甲基、二氟甲基、三氟甲基、三氯甲基、二氟氯甲基和二氯氟甲基。
C1-C6表示含有1至6个碳原子。取代基定义中出现的烷基可以是直链或支链的,并且是例如甲基、乙基、正丙基、 正丁基、正戊基、正己基、异丙基、正丁基、仲丁基、异丁基或叔丁基。烷氧基衍生自所提及的烷基。烷氧基是例如甲氧基、乙氧基、丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基和叔丁氧基;优选甲氧基和乙氧基。
本发明首先公开了一种式I 化合物及其立体异构体和其盐,
I,
其中,R选自H、卤素、C1-C4烷基和C1-C4卤代烷基。
优选地的技术方案中,R为卤代甲基,优选氟甲基、二氟甲基和三氟甲基。
本发明中特别优选的化合物为:。
在本说明书中,如果在化学名称和化学结构间存在任何差异,结构是占优的。一般地,本发明的化合物可以通过本发明所描述的方法制备得到,除非有进一步的说明。下面的合成方案和实施例用于进一步举例说明本发明的内容。
本发明式I化合物通过下列合成方案合成得到:
,其中,R选自H、卤素、C1-C4烷基和C1-C4卤代烷基。
式II化合物与酰化试剂反应后形成的酰氯化合物与式III化合物合成制备得到式I化合物,所述的酰化试剂选自氯化亚砜、草酰氯;反应优选在溶剂中进行,所述的溶剂包括芳烃,例如苯、二甲苯、甲苯等;氯代烃,例如氯代苯、氯乙烯、三氯甲烷、二氯甲烷,反应温度为20-80℃,反应优选在碱存在的条件下进行,所述的碱为三乙胺,吡啶,碳酸钾,碳酸钠等,但不限于此。
所属领域的技术人员将认识到:本发明所描述的化学反应可以用来合适地制备许多本发明的其他化合物,且用于制备本发明的化合物的其它方法都被认为是在本发明的范围之内。例如,根据本发明那些非例证的化合物的合成可以成功地被所属领域的技术人员通过修饰方法完成,如适当的保护干扰基团,通过利用其他已知的试剂(除了本发明所描述的),或将反应条件做一些常规的修改。另外,本发明所公开的反应或已知的反应条件也公认地适用于本发明其他化合物的制备。
本发明还提供一种组合物,包含本发明式I化合物和至少一种助剂,所述助剂选自表面活性剂、固体稀释剂和液体稀释剂。
本发明所述的化合物或组合物在防治植物病害中的应用。
本发明的化合物一般可用作组合物即制剂中杀菌剂的活性成分,通常还包括农药学上可接受的表面活性剂和载体。载体可以是固体载体或液体载体。
所述的固体载体包括天然的或合成的粘土和硅酸盐,例如天然硅石和硅藻土;硅酸镁,例如滑石;硅酸铝镁,例如高岭石、高岭土、蒙脱土和云母;白炭黑、碳酸钙、轻质碳酸钙;硫酸钙;石灰石;硫酸钠;铵盐,如硫酸铵、六甲撑二胺和尿素等。
所述的液体载体包括水和有机溶剂,当用水做溶剂或稀释剂时,有机溶剂也能用做辅助剂或防冻添加剂。有用的液化的气态填充剂或载体是那些在标准温度及标准压力下为气态的液体,例如气溶胶推进剂,如卤代烃,以及丁烷、丙烷、氮气和二氧化碳等等。所述的合适的有机溶剂包括芳烃,例如苯、二甲苯、甲苯等;氯代烃,例如氯代苯、氯乙烯、三氯甲烷、二氯甲烷等;脂肪烃,例如石油馏分、环己烷、轻质矿物油;醇类,例如异丙醇、丁醇、乙二醇、丙三醇和环己醇等;以及它们的醚和酯;酮类,例如丙酮、环己酮以及二甲基甲酰胺和N-甲基-吡咯烷酮,植物油,例如大豆油、菜籽油和棉籽油等等,但不限于此。
合适的表面活性剂(佐剂、乳化剂、分散剂、保护性胶体、润湿剂和粘合剂)包括所有常见的离子和非离子物质,例如乙氧基化的壬基酚、直链或支链醇的聚亚烷基二醇醚、烷基酚与环氧乙烷和/或环氧丙烷的反应产物、脂肪酸胺与环氧乙烷和/或环氧丙烷的反应产物,以及脂肪酸酯、烷基磺酸盐、烷基硫酸盐、烷基醚硫酸盐、烷基醚磷酸盐、芳基硫酸盐、乙氧基化的芳基烷基酚(如三苯乙烯基-苯酚-乙氧基化物),以及乙氧基化的和丙氧基化的芳基烷基酚如硫酸化和磷酸化的芳基烷基酚-乙氧基化物和-乙氧基和-丙氧基化物。如果所述活性成分之一和/或所述惰性载体之一不溶于水且施用在水中进行时,则表面活性剂的存在是必要的。
本发明所述组合物可以以其制剂形式或由其制备的使用形式施用,所述使用形式例如气溶胶、胶囊悬浮剂、热雾浓缩剂、胶囊化的颗粒剂、细颗粒剂、用于种子处理的种衣剂、可撒粉的粉剂、可乳化的浓缩剂、水包油乳剂、油包水乳剂、大颗粒剂、微颗粒剂、油分散性粉末剂、油混溶性流动浓缩剂、油混溶性液体、气剂(在压力下)、产气产品、泡沫剂、糊剂、悬浮浓缩剂、悬乳浓缩剂、可溶性浓缩剂、混悬剂、可湿性粉剂、可溶性粉剂、粉剂和颗粒剂、水溶性和水分散性的颗粒剂或片剂、用于种子处理的水溶性或水分散性粉剂,可湿性粉剂、经活性物质浸渍的天然产物及合成物质,以及聚合物和种子包衣材料中的微胶囊。
本发明所述的制剂还可以含有其他组分,例如其他的杀菌剂、杀虫剂、除草剂、植物生长调节剂、引诱剂、杀螨剂、杀线虫剂、肥料、安全剂等能够与液体肥料或固体、粒状肥料载体比如硝酸铵、尿素等一起配制或与细砂或泥土混合。
本发明涉及所述化合物或包含所述化合物的组合物在农业或园林中用作杀菌剂剂的用途,用于控制或防止有用植物受到病害的侵害。
在本发明的范围内,有用植物包括以下植物种类:谷物(小麦、大麦、黑麦、燕麦、稻、玉米、高粱以及相关物种);甜菜(糖萝卜以及饲用甜菜);梨果、核果以及软水果(苹果、梨、李子、桃、扁桃、樱桃、草莓、覆盆子和黑莓);豆科植物(扁豆、宾豆、豌豆、大豆);油料作物(油菜、芥菜、橄榄、向日葵、椰子、蓖麻油植物、可可豆、落花生或大豆);瓜类植物(南瓜、黄瓜、甜瓜);纤维植物(棉花、亚麻、大麻、黄麻);柑橘属水果(桔子、柠檬、葡萄柚、柑橘);蔬菜(菠菜、莴苣、芦笋、甘蓝、胡萝卜、洋葱、番茄、马铃薯、红椒);月桂类植物(鳄梨、樟属、樟脑)或植物,例如烟草、坚果、咖啡、茄子、甘蔗、茶、胡椒、葡萄藤、啤酒花、香蕉以及天然橡胶植物,连同草皮、观赏和森林植物,例如花卉、灌木、阔叶树或常绿树,例如针叶树,以及植物繁殖材料。
本发明所述组合物的施用剂量根据天气条件、剂型、施用时机、施用方法、施用面积、目标作物等变化。
制备实施例
下面结合实施例对本发明进行进一步的说明,除非特别说明制备本发明的化合物所使用的原料、试剂等等均是可以商购的,或者可以通过本领域常规的方法制备得到。
实施例 1 N-(3-异丙氧基苯基)-2-甲砜基-4-(三氟甲基)苯甲酰胺(PPN-FL-01)的合成
在装有搅拌器、回流冷凝管和温度计的1000 mL反应瓶中,通入N2,加入100 mL二氯乙烷,0.1mol2-甲砜基-4-三氟甲基苯甲酸, 0.1gDMF,加热回流,开始滴加0.12mol氯化亚砜,滴加2h,HPLC分析检测2-甲砜基-4-三氟甲基苯甲酸<0.5%,反应完毕,加入吡啶0.2mol,加入100ml二氯乙烷,0度滴加间异丙氧基苯胺0.2mol,2h滴加完毕,缓慢升温至室温反应10h,HPLC检测反应完毕,加入乙酸乙酯200ml,加入100ml水,搅拌20min,静置分层,有机相脱溶,用乙酸乙酯结晶得到白色固体产品,含量98%,收率70%。
1H NMR (500 MHz, DMSO) δ 10.72 (s, 1H,H-1), 8.27 (m, 2H,H-2, H-2’),7.99 (d,J= 7.7 Hz, 1H,H-3), 7.33 (m, 1H,H-4), 7.25 (t,J= 8.1 Hz, 1H,H-5),7.18 (d,J= 8.0 Hz, 1H,H-6), 6.71 (dd,J= 8.1, 1.9 Hz, 1H,H-7), 4.63 – 4.52 (m,J = 6.0 Hz,1H,H-8), 3.47 (s, 3H,H-9), 1.28 (d,J= 6.0 Hz, 6H,H-10).
实施例 2 N-(3-异丙氧基苯基)-2-甲砜基-4-(三氟甲基)苯甲酰胺的合成
在装有搅拌器、回流冷凝管和温度计的1000 mL反应瓶中,通入N2,加入100 mL二氯乙烷,0.1mol2-甲砜基-4-三氟甲基苯甲酸, 0.1gDMF,加热回流,开始滴加0.12mol草酰氯,滴加2h,HPLC分析检测2-甲砜基-4-三氟甲基苯甲酸<0.5%,反应完毕,加入吡啶0.2mol,加入100ml二氯乙烷,0度滴加间异丙氧基苯胺0.2mol,2h滴加完毕,缓慢升温至室温反应10h,HPLC检测反应完毕,加入乙酸乙酯200ml,加入100ml水,搅拌20min,静置分层,有机相脱溶,用乙酸乙酯结晶得到白色固体产品,含量98%,收率65%。
1H NMR (500 MHz, DMSO) δ 10.72 (s, 1H,H-1), 8.27 (m, 2H,H-2, H-2’),7.99 (d,J= 7.7 Hz, 1H,H-3), 7.33 (m, 1H,H-4), 7.25 (t,J= 8.1 Hz, 1H,H-5),7.18 (d,J= 8.0 Hz, 1H,H-6), 6.71 (dd,J= 8.1, 1.9 Hz, 1H,H-7), 4.63 – 4.52 (m,J = 6.0 Hz,1H,H-8), 3.47 (s, 3H,H-9), 1.28 (d,J= 6.0 Hz, 6H,H-10).
生物活性测定
1供试药剂制备
1.1试验材料与药品
PPN-FL-01(98.5%原药)、氟酰胺(98.5%)、丙酮(AC)、吐温80、水。
1.2 药剂的制备
(1)1%PPN-FL-01母液制备:用丙酮作溶剂制备。
(2)0.1%氟酰胺母液制备: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。
(5)CK为水空白对照。
2、PDA培养基制备:
(1)称量和熬煮:按培养基配方逐一称取去皮土豆700g。土豆切成小块放入锅中,加水3500ml,在加热器上加热至沸腾,维持20-30min,用可用2层纱布趁热在量杯上过滤,滤渣弃取。滤液补充水分到3500ml。
(2)加热溶解:把滤液放入锅中,加入葡萄糖70g,琼脂55g,然后小火加热,并用玻棒不断搅拌,以防琼脂糊底或溢出,待琼脂完全溶解后,再补充水分至所需量。
(3)分装:按实验要求,将配制的培养基分装入250ml三角锥形瓶(装100ml)和500ml三角锥形瓶(装300ml)。
(4)高压灭菌:121℃ 20min。
3、测试方法
将测试化合物制备成浓度为0.0155ppm、0.125ppm、0.50ppm采用生长速率法,将配制好的药剂取11.11ml加入冷却至50-60℃含100ml培养基的三角锥形瓶中,混合均匀,倒平板。待平板冷却后,在平板中间接入直径为6mm的菌饼,盖上皿盖,每个处理3次重复,置于湿度为65%,温度为25℃的培养箱培养。
4、调查时间和方法
药后3d,直径采用十字交叉法测量菌落直径,取平均值,计算各药剂处理对水稻纹枯病菌菌丝生长的抑制率。
5、数据分析和统计
化合物的活性以真菌生长抑制的形式进行表示 (0=无生长抑制,80%至 99%的等级意味着良好至非常良好的抑制,100%=完全抑制 )。
表1本发明化合物对对水稻纹枯病菌的防治效果数据。
由表1和结果可以看出本发明化合物在低浓度的情况下杀菌效果要明显优于氟酰胺。
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 (6)
1.一种式I 化合物及其立体异构体和其盐,
I,
其中,R选自H、卤素、C1-C4烷基和C1-C4卤代烷基。
2.根据权利要求1所述式I 化合物及其立体异构体和其盐,其特征在于,R为卤代甲基,优选氟甲基、二氟甲基和三氟甲基。
3.根据1或2所述的式I 化合物及其立体异构体和其盐,其特征在于,化合物为:
。
4.一种制备权利要求1-3任一项所述的式I 化合物及其立体异构体和其盐的方法,其特征在于,式II和式III化合物进行反应制备得到式I化合物,其合成路线如下:
,其中,R基团的定义如权利要求1-3所定义。
5.一种组合物,其特征在于,包含权利要求1-3任一项所述化合物。
6.权利要求1-3任一项所述的化合物或权利要求5所述的组合物在防治植物病害中的应用。
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