CN1390838A - 吡喃酮类化合物及其用途 - Google Patents
吡喃酮类化合物及其用途 Download PDFInfo
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- CN1390838A CN1390838A CN02122421A CN02122421A CN1390838A CN 1390838 A CN1390838 A CN 1390838A CN 02122421 A CN02122421 A CN 02122421A CN 02122421 A CN02122421 A CN 02122421A CN 1390838 A CN1390838 A CN 1390838A
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
- C07D309/38—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms one oxygen atom in position 2 or 4, e.g. pyrones
-
- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
- A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
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- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrane Compounds (AREA)
Abstract
式(1)的吡喃酮化合物,其中R代表三氟甲基、氢原子或甲基,对于控制害虫具有良好的效果。
Description
技术领域
本发明涉及吡喃酮类化合物及其农药用途。
背景技术
JP 51-19126 A公开了某些吡喃酮类化合物具有杀昆虫/杀螨活性。然而,这些化合物的控制害虫效果尚不能令人满意。
发明内容
本发明提供下式(1)化合物:其中:R代表三氟甲基、氢原子或甲基;含有上述化合物作为活性成分的杀虫组合物和控制害虫的方法,所述方法包括:把上述化合物施用于害虫或害虫居留的地方。
本发明化合物具有良好的杀虫活性。
下面说明本发明化合物的制备方法。
通常在缩合剂(如二环己基碳二亚胺)和4-二甲氨基吡啶的存在下,在溶剂中进行该反应。
反应所用的溶剂例子包括:脂肪烃类例如己烷、庚烷、辛烷和壬烷;芳烃类例如甲苯、二甲苯和1,3,5-三甲苯;卤代烃类例如氯苯、二氯苯和三氟甲苯;醚类例如二异丙基醚、1,4-二氧六环、四氢呋喃、乙二醇二甲基醚和二乙二醇二甲基醚;酰胺类例如N,N-二甲基甲酰胺和N,N-二甲基乙酰胺;含硫溶剂例如二甲亚砜和环丁砜;以及这些溶剂的混合物。
在上述反应中,基于1摩尔式(2)化合物,式(3)化合物的用量为0.7-1.5摩尔。
基于1摩尔式(2)化合物,缩合剂的用量为1-5摩尔,4-二甲氨基吡啶的用量为0.01-1摩尔。
反应温度通常为0-100℃,反应时间取决于反应温度,通常为1-48小时。
反应结束后,可以把反应混合物进行例如过滤、用酸性水洗涤滤液,干燥后浓缩,任选地纯化,例如用色谱纯化,得到被分离的本发明化合物产品。
本发明显示控制效果的害虫例子包括下列节肢动物:
半翅目害虫:飞虱科(植物跳虫)[例如Laodelphax striatellus(棕色小植物跳虫)、稻褐飞虱(棕色植物跳虫)和白背飞虱(白色背部的稻类植物跳虫)、Deltocephalidae(leafhoppers)[例如:黑尾叶蝉、二点黑尾叶蝉和Recilia dorsalis]、蚜科(蚜虫)、臭虫、粉虱科(粉虱)、鳞片、网蝽科(网蝽)和木虱科(suckers);
鳞翅目昆虫:Pyralidae[例如:二化螟(rice stem borer)、稻纵卷叶虫(rice leafroller)和Plodia interpunctella(印度谷螟)]、夜蛾科[例如Spodoptera litura(烟草切根虫)、东方粘虫(稻粘虫)、Mamestra brassicae(甘蓝夜蛾)、Plusiinae、含有黄地老虎(芜菁切根虫)和小地老虎(黑色切根虫)的Agrotis spp.、Helicoverpa spp.和Heliothis spp.]、粉蝶科[例如菜粉蝶]、卷叶蛾科[例如Adoxophyes spp.]、果蛀蛾科、潜蛾科、毒蛾科、巢蛾科[例如小菜蛾]、弄蝶科[例如直纹稻苞虫]、谷蛾科[例如Tineatranslucens(网衣蛾)和幕衣蛾(webbing clothes moth)];
双翅目害虫:库蚊属[例如,库蚊属pipiens pallens和三带喙库蚊]、伊蚊属[例如埃及伊蚊(黄热蚊)和白纹伊蚊]、按蚊属[例如按蚊属sinensis]、摇蚊科(蠓)、蝇科[例如蝇属domestica(家蝇)、厩腐蝇(伪家蝇)和黄腹厩蝇(小家蝇)]、丽蝇科、麻蝇科、花蝇科[例如Delia platura(谷种蛆)和Delia antiqua(洋葱蛆)]、实蝇科(果蝇)、果蝇科(蜂蝇)、毛蠓科(沙蝇)、虻科、蚋科(墨蚊)、螫蝇科(厩螫蝇)、蚤蝇科和蠓科(咬蠓(biding midges));
鞘翅目害虫:玉米根虫[例如玉米幼芽根叶虫甲(西方玉米根虫)和十一星爪叶甲(南方玉米根虫)]、金龟科[例如大绿丽金龟和Anomalarufocuprea]、象虫科(象鼻虫)[例如玉米象(玉米象鼻虫)和美洲稻象甲(米汤象鼻虫)、皮蠹科[例如Authrenus verbasci和Attagenusunicolor japonicus]、拟步行虫科(拟步甲)[例如黄粉甲(大黄粉虫幼体)和直拟谷盗(红色面粉甲虫)、叶甲总科(金花虫)[例如稻负泥虫(稻叶甲虫)、曲条跳甲(斑纹跳蚤甲虫)和黄守瓜(葫芦叶甲虫)、番死虫科、瓢虫科(瓢虫)[例如Epilachna vigintioctopunctata]、Lyctidae(powderpost甲虫)、长蠹科、天牛总科和隐翅虫科[例如隐翅虫属fuscipes];
网翅目害虫:德国小蠊(德国蟑螂)、烟色大蠊(棕灰色蟑螂)、美洲蜚蠊(美国蟑螂)、褐色大蠊(褐色蟑螂)和东方蜚蠊等;
缨翅目害虫:蓟马科[例如棕黄蓟马、苜宿蓟马(西方花蓟马)和Thrips hawaiiensis(花蓟马)];
膜翅目害虫:蚁科(蚂蚁)、胡蜂科[例如大黄蜂和长腿黄蜂];肿腿蜂科和叶蜂科(锯蜂)[例如日本芜情叶蜂(卷心菜锯蜂)];
直翅目害虫:蝼蛄科(蝼蛄)和蝗科(蝗虫);
蚤目害虫:犬属栉头蚤属(犬蚤)、猫属栉头蚤属(猫蚤)和Pulexirritans(人蚤);
虱目害虫:humanus corporis、Pediculus capitis和阴虱(蟹虱);
等翅目害虫:Reticulitermes speratus和家白蚁;
螨目害虫:叶螨科(蜘蛛螨)[例如红叶螨(深红色蜘蛛螨)、棉叶螨(二点蜘蛛螨)、神泽叶螨(Kanzawa蜘蛛螨)、柑桔全爪螨(柑橘属果树红螨)和苹果全爪螨(欧洲红螨)]、硬蜱科[例如牛蜱属microplus和血蜱属longiconis]、螨科[例如腐食酪螨(copra mite)和椭圆嗜粉螨]、刺皮螨科[例如美洲家刺皮螨(美洲家尘埃螨)和Dermatophagoides ptrenyssnus]、食甜螨科[例如隐秘食甜螨、家食甜螨和Glycyphagus destructor]、肉食螨总科[例如马六甲肉食螨和Cheyletus fortis]、似虱螨科、Chortoglyphus spp.和Haplochthonius spp.;
等脚目害虫:木虱[例如鼠妇和Porcellionides pruinosus]和pill-bugs[例如平甲虫]。
本发明的杀虫剂组合物含有本发明的化合物和惰性载体例如固体载体、液体载体、气体载体和/或饵类物质(毒饵物质)。本发明化合物可以浸渗于基质材料(例如多孔陶质板、非织物类布料、纸、蚊香基质中)。另外,本发明的杀虫剂组合物可以任选地含有表面活性剂或其它辅料从而用于配制成油状溶液、可乳化浓缩物、可湿性粉剂、流动性制剂、粒剂、粉尘、气溶胶、成雾剂、热熏剂、烟熏剂、毒饵、微囊制剂、ULV制剂、斑点制剂、倾倒制剂、香波制剂、片形制剂和树脂制剂等等。
在这些制剂中,本发明化合物的通常含量为0.01-95重量%。
所述制剂所用的固体载体例子包括:粘土的细粉或颗粒(例如高岭土、硅藻土、合成水合氧化硅、膨润土、Fubasami粘土、酸粘土)、滑石、陶瓷、肥料(例如硫酸铵、磷酸铵、硝酸铵、氯化铵、尿素)和其它无机材料(例如绢云母、石英、硫磺、活性碳、碳酸钙、水合氧化硅)。
液体载体的例子包括:水、醇(例如甲醇、乙醇)、酮类(例如丙酮、甲基乙基酮)、芳烃(例如甲苯、二甲苯、乙基苯和甲基萘)、脂肪烃(例如己烷、环己烷、煤油、汽油)、酯类(乙酸乙酯、乙酸丁酯)、腈类(例如乙腈、异丁基腈)、醚类(例如二异丙基醚、二氧六环)、酰胺类(例如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺)、卤代烃类(二氯甲烷、三氯乙烷、四氯化碳)、有机硫化合物(例如二甲亚砜)和植物油(例如豆油、棉籽油)。
气体载体的例子包括碳氟化合物、丁烷气体、LPG(液化石油汽)、二甲基醚和二氧化碳。
表面活性剂的例子包括:烷基硫酸盐、烷基磺酸盐、烷基芳基磺酸盐、烷基芳基醚、聚氧乙烯烷基芳基醚、聚乙二醇醚、多元醇酯和糖醇衍生物。
其它辅料的例子包括:粘附剂、分散剂和稳定剂,通常为酪蛋白、明胶、多糖(例如淀粉、阿拉伯胶、纤维素衍生物、海藻酸)、木质素衍生物、合成水溶性聚合物(例如聚乙烯醇、聚乙烯吡咯烷酮、聚丙烯酸)、PAP(酸异丙基磷酸酯)、BHT(2,6-二叔丁基-4-甲基苯酚)、BHT(2-叔丁基-4-甲氧基苯酚)、BHA(2-叔丁基-4-甲氧基苯酚和3-叔丁基-4-甲氧基苯酚的混合物)、植物油、矿物油、脂肪酸和脂肪酸酯。
毒饵的基质物质包括:饵成分(例如谷类粉末、植物油、糖、纤维素)、抗氧化剂(例如二丁基羟基甲苯、去甲二氢愈创木酸)、防腐剂(例如脱氢乙酸)、防止儿童和宠物误食的物质(例如:红辣椒粉)、害虫引诱调味剂(例如乳酪调味剂、洋葱调味剂和花生油)。
当应用本发明的杀虫剂组合物来控制农业和林业害虫时,本发明化合物的施用剂量通常为1-10000g/公顷。用水将可乳化浓缩物、可湿性粉末和可流动制剂稀释至10-10000ppm的浓度,然后应用它们。粒剂和粉尘通常按照制备剂型应用。这些制剂可以直接施用于害虫,或者施用于农作物植物使其免受害虫侵害。而且,可以将它们施用于土壤用于控制在土壤中生长的害虫。
当将本发明的杀虫剂组合物应用于卫生学领域时,用水将可乳化浓缩物、可湿性粉末和流动性制剂稀释至0.01-10000ppm浓度,然后将其施用于害虫或害虫居留之处。油溶液、气溶胶、烟熏剂和毒饵可以按照制备的剂型施用于害虫或害虫居留之处。如果是熏剂,则将其加热从而使活性成分挥发至害虫居留之处。本发明化合物的应用剂量通常为0.001-5g/m2面积或0.01-10g/m3空间。
可以把本发明组合物与下列物质联合应用:其它杀虫剂、杀螨剂、杀线虫剂、杀真菌剂、除草剂、植物生长调节剂、增效剂、肥料、土壤改良剂和动物食品等。
杀虫剂、杀螨剂和杀线虫剂的例子包括:有机磷化合物例如杀螟松、倍硫磷、二嗪农、毒死蜱、高灭磷、杀扑磷、乙拌磷、DDVP、硫灭克磷、杀螟腈、dioxabenzofos、乐果、稻丰散、马拉硫磷、敌百虫、保棉磷、久效磷和乙硫磷;氨基甲酸酯类化合物例如BPMC、benfracarb、残杀威、carbosulfan、甲萘威、灭多虫、杀虫丹、涕灭威、草氨酰和fenothiocarb;拟除虫菊酯类化合物例如依托菲诺西、杀灭菊酯、esfenvalerate、分朴葡酯、氯氰菊酯、扑灭司林、格林奈、溴氰菊酯、cycloprothrin、氯氟胺氰戊菊酯、bifenthrin、tralomethrin、silafluofen、d-苯氧司林、d-丙烯菊酯、cyphenothrin、d-灭虫菊、actinathrin、cyfluthrin、tefluthrin、transfluthrin、四甲司林、丙烯菊酯、prallethrin、empenthrin、imiprothrin和d-furamethrin;噻二嗪衍生物例如稻虱净;硝基咪唑烯类衍生物;环联硫甲胺衍生物例如杀螟丹、杀虫环和bensultap;新尼古丁类(neonicotinoid)化合物例如acetamiprid、thiamethoxam和thiacloprid;氯代烃类例如硫丹、γ-BHC和DDT;苯甲酰基苯脲类化合物例如chlorfluazuron、teflubenzuron和flufenoxuron;甲脒衍生物例如虫螨脒和克死螨;硫脲类衍生物例如diafenthiuron;苯基吡唑类化合物;metoxadiazone;溴螨酯;三氯杀螨砜;灭螨猛;克螨特;杀螨锡;hexythiazox;clofentezine;pyridaben;fenpyroximate;tebufenpyrad;多萘菌素络合物(四抗菌素、二活菌素和三活菌素);pyrimidifen;milbemectin;阿巴美丁;伊维菌素和印苦辣子素[AZAD]。
具体实施方式
实施例
本发明将通过制备实施例、制剂实施例和测试实施例作进一步举例说明,当然本发明无论在任何意义上均不限于这些实施例。
制备实施例如下。制备实施例1
将14.1g 4-羟基-6-甲基-2-吡喃酮悬浮于240ml甲苯中,然后往其中加入1.94g 4-二甲氨基吡啶、16.6g 4,4,4-三氟丁酸和21.9g二环己基碳二亚胺。将反应混合物室温搅拌1小时,然后继续在70℃下搅拌20小时。冷却至室温后过滤,用1%盐酸洗涤滤液两次,用饱和盐水洗涤一次。用无水硫酸钠干燥有机层,减压浓缩。残余物经过硅胶色谱得到5.38g 4-羟基-6-甲基-3-(4,4,4-三氟丁酰)-2-吡喃酮(此后称本发明化合物(A))。
熔点:104℃。1H-NMR(250MHz,CDCl3/TMS):δ(ppm)16.01(s,1H)、5.98(s,1H)、3.38(t,J=7.5Hz,2H)、2.62-2.42(m,2H)、2.30(s,3H)。制备实施例2
按照与制备实施例1相同的方式,从2.00g 4-羟基-6-甲基-2-吡喃酮、240mg 4-二甲氨基吡啶、2.48g 3-甲基-4,4,4-三氟丁酸、3.27g二环己基碳二亚胺和100ml甲苯制备得到0.46g 4-羟基-6-甲基-3-(3-三氟甲基丁酰基)-2-吡喃酮(下文被称为本发明化合物(B))。
熔点:69℃。1H-NMR(250MHz,CDCl3/TMS):δ(ppm)16.17(s,1H)、5.97(s,1H)、3.41(dd,J=18.3,4.1Hz,1H)、3.18(dd,J=18.3,8.6Hz,1H)、3.10-2.90(m,1H)、2.29(s,3H)、1.18(d,J=6.8Hz,3H)制备实施例3
按照与制备实施例1相同的方式,从1.58g 4-羟基-6-甲基-2-吡喃酮、220mg 4-二甲氨基吡啶、2.50g 3-三氟甲基-4,4,4-三氟丁酸、2.60g二环己基碳二亚胺和70ml甲苯制备得到0.17g 4-羟基-6-甲基-3-(3-三氟甲基丁酰基)-2-吡喃酮(下文被称为本发明化合物(C))。
熔点:73℃。1H-NMR(300MHz,CDCl3/TMS):δ(ppm)15.48(s,1H)、6.01(s,1H)、4.15-4.00(m,1H)、3.60(d,J=5.3Hz,2H)、2.32(s,3H)
下面描述制剂实施例,份数指重量份数。制剂实施例1
把10份本发明化合物(A)、(B)或(C)、17.5份聚氧乙烯烷基醚硫酸铵和17.5份二氧化硅与55份水在湿粉碎状态下混合得到各个制剂。制剂实施例2
把50份本发明化合物(A)、(B)或(C)、3份木质素磺酸钙、2份十二烷基硫酸钠和45份合成水合氧化硅充分粉碎并充分混合得到各个可湿性粉剂。制剂实施例3
将两份本发明化合物(A)、(B)或(C)、88份高岭土和10份滑石充分粉碎和混合得到各个粉末。制剂实施例4
将20份本发明化合物(A)、(B)或(C)、14份聚氧乙烯苯乙烯基苯基醚、6份十二烷基苯磺酸钙和60份二甲苯充分混合,得到各个可乳化浓缩物。制剂实施例5
将两份本发明化合物(A)、(B)或(C)、1份合成水合氧化硅、2份木质素磺酸钙、30份膨润土和65份高岭土充分粉碎和混合,用水捏合,然后制粒,干燥得到各种颗粒。制剂实施例6
将20份本发明化合物(A)、(B)或(C)、1.5份脱水山梨醇三油酸酯和28.5份含有2份聚乙烯醇的水溶液混合,用砂研磨机粉碎制备成直径为3μm或更小的颗粒。往其中加入40份含有0.05份黄原胶和0.1份硅酸铝镁的水溶液,然后将其与10份丙二醇混合得到20%的各个流动性制剂。制剂实施例7
将0.1(1/10)份本发明化合物(A)、(B)或(C)溶解于5份二甲苯和5份三氯乙烷中,然后将其与89.9份防臭煤油相混合得到各个0.1%的油溶液。制剂实施例8
将0.1份本发明化合物(A)、(B)或(C)、0.2份四甲司林和0.1份d-苯氧司林用10份三氯乙烷和59.6份除臭煤油溶解,把得到的溶液填充至气溶胶容器中。然后将该容器装上阀,并通过该阀将30份抛射剂(液化石油气)在加压下装入气溶胶容器,得到各个油基质气溶胶。制剂实施例9
将0.2份本发明化合物(A)、(B)或(C)、0.2份d-丙烯菊酯、0.2份d-苯氧司林、5份二甲苯、3.4份除臭煤油和1份Atmos300(乳化剂;Atlas Chemical Co.的商品)的混合物与50份纯净水填充到气溶胶容器中。然后将容器装上阀,通过该阀将40份抛射剂(液化石油气)在加压下装入气溶胶容器中得到各个水基质气溶胶。制剂实施例10
将0.3g本发明化合物(A)、(B)或(C)和0.3g d-丙烯菊酯溶解于20ml丙酮中,将制备得到的溶液与99.4g蚊香载体(Tabu粉末、Pyrethrum marc和木粉以4∶3∶3的比例得到的混合物)均匀地混合。加入120ml水后,将混合物充分捏合,铸模干燥后得到各个蚊香。制剂实施例11
把0.4g本发明化合物(A)、(B)或(C)和0.4g胡椒基丁醚溶解于丙酮中制备10毫升(10ml)溶液。将半毫升(0.5ml)获得的溶液用mosquito-mat(纸浆和棉绒混合物的压缩原纤维板:2.5cm×1.5cm×0.3cm)均匀地浸渗,得到各个mosquito-mats。制剂实施例12
把10mg本发明化合物(A)、(B)或(C)溶解于0.5ml丙酮中,将制备的溶液均匀地与5g固体饲料粉末混合(用于饲养的固体饲料粉末:由日本Kurea有限公司制备的CE-2)。然后经空气干燥除去丙酮得到各个0.5%的毒饵。制剂实施例13
用非织物布料浸渗含有本发明化合物(A)、(B)或(C)的丙酮溶液,使得本发明化合物的浓度为1g/1m2,将丙酮空气干燥后得到各个杀螨薄片。
下列测试实施例表明:本发明化合物作为活性成分能够用于控制有害的节肢动物。测试实施例1
将5.5cm直径的滤纸置于聚乙烯杯(直径5.5cm)底部。把按照制剂实施例1制备的测试化合物试剂稀释后获得0.7ml 500ppm的水稀释液,将其滴至滤纸上,往其中分散30mg蔗糖。将两只雄性德国蟑螂(Blattella germanica)放入带盖的聚乙烯杯中。经六天后,检测德国蟑螂的死亡数目。结果发现:本发明化合物(A)、(B)和(C)显示100%的死亡率。测试实施例2
将5.5cm直径的滤纸置于聚乙烯杯(直径5.5cm)底部。把按照制剂实施例1制备的测试化合物试剂稀释后获得0.7ml 500ppm的水稀释液,将其滴至滤纸上,往其中分散30mg蔗糖。将两只雌性家蝇(Muscadomestica)放入该带盖的杯中。经1天后,检测家蝇的死亡数目。结果发现:本发明化合物(A)、(B)和(C)显示100%的死亡率。
把本发明化合物(A)和参照化合物各自用丙酮稀释得到溶液(30g/l)。
用微注射器将丙酮溶液(0.5μl)施用于10只雌性家蝇(Muscadomestica)的后胸部区域(活性成分:约15μg/家蝇),然后将家蝇放入装上水和饲料的塑料杯中。经24小时后,检测死亡率(%)(三次重复值)。结果如下。
死亡率(%) | |
本发明化合物(A)参照化合物 | 1003.3 |
Claims (10)
1.式(1)的吡喃酮化合物,其中R代表三氟甲基、氢原子或甲基。
2.权利要求1的吡喃酮化合物,其中R代表三氟甲基。
3.权利要求1的吡喃酮化合物,其中R代表氢原子。
4.权利要求1的吡喃酮化合物,其中R代表甲基。
5.含有式(1)吡喃酮化合物和载体的杀虫剂组合物,其中R代表三氟甲基、氢原子或甲基。
6.权利要求5的杀虫剂组合物,其中R代表三氟甲基。
7.权利要求5的杀虫剂组合物,其中R代表氢原子。
8.权利要求5的杀虫剂组合物,其中R代表甲基。
9.控制害虫的方法,其包括:将有效量的式(1)吡喃酮化合物施用于害虫或害虫居留之处,其中R代表三氟甲基、氢原子或甲基。
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JP2001173728A JP2002363174A (ja) | 2001-06-08 | 2001-06-08 | ピロン化合物及びその用途 |
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JP (1) | JP2002363174A (zh) |
KR (1) | KR20020093570A (zh) |
CN (1) | CN1200936C (zh) |
AU (1) | AU780731B2 (zh) |
BR (1) | BR0202092A (zh) |
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CN104430352A (zh) * | 2014-12-31 | 2015-03-25 | 江阴苏利化学股份有限公司 | 一种含有吡喃酮的防治水稻二化螟的农药组合物的新应用 |
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CH514573A (de) | 1969-05-29 | 1971-10-31 | Lonza Ag | Verfahren zur Herstellung von 3-Halogenacetyl-6-halogenmethyl-2,4-dioxo-2,3-dihydro-4-H-pyran |
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CN104430352A (zh) * | 2014-12-31 | 2015-03-25 | 江阴苏利化学股份有限公司 | 一种含有吡喃酮的防治水稻二化螟的农药组合物的新应用 |
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KR20020093570A (ko) | 2002-12-16 |
ITTO20020476A1 (it) | 2003-12-09 |
ITTO20020476A0 (it) | 2002-06-07 |
US6509299B2 (en) | 2003-01-21 |
AU780731B2 (en) | 2005-04-14 |
ES2200689A1 (es) | 2004-03-01 |
US20020197294A1 (en) | 2002-12-26 |
CN1200936C (zh) | 2005-05-11 |
JP2002363174A (ja) | 2002-12-18 |
AU4244502A (en) | 2002-12-12 |
ES2200689B1 (es) | 2005-05-01 |
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