CN112313215B - 尿嘧啶化合物及含有它的有害节肢动物防除组合物 - Google Patents
尿嘧啶化合物及含有它的有害节肢动物防除组合物 Download PDFInfo
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- 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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- 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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- 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
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- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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Abstract
本发明提供一种对有害节肢动物具有优异的防除效力的、式(A)所示的化合物。
Description
技术领域
本专利申请基于日本专利申请2018-128122号(2018年7月5日申请)主张巴黎公约上的优先权及利益,并引用于此,由此将上述申请中记载的全部内容纳入本说明书中。
本发明涉及尿嘧啶化合物及其有害节肢动物防除组合物。
背景技术
迄今为止,出于防除有害节肢动物的目的,研究过各种各样的化合物,并供于实用(参照非专利文献1)。专利文献1中,作为枯萎剂记载有式(B)所示的化合物(以下记作化合物B):
[化1]
现有技术文献
专利文献
专利文献1:美国专利第7109148号说明书
非专利文献
非专利文献1:The Pesticide Manual-17th edition(BCPC刊)ISBN 978-1-901396-88-1
发明内容
发明所要解决的问题
本发明的课题在于,提供一种对植物病害具有优异的防除效力的化合物。
用于解决问题的手段
本发明人对上述课题进行了研究,结果发现,下述式(A)所示的化合物对有害节肢动物具有优异的防除效力,从而完成了本发明。
本发明如下所示。
[1]一种化合物(以下记作化合物A),其由式(A)表示:
[化2]
[2]一种组合物(以下记作本发明组合物),其含有[1]中记载的化合物和非活性载体。
[3]一种有害节肢动物的防除方法(以下记作本发明防除方法),其将[1]中记载的化合物的有效量施用于有害节肢动物或有害节肢动物的栖息场所。
发明效果
根据本发明,可以防除有害节肢动物。
具体实施方式
本发明的组合物含有化合物A和非活性载体。本发明的组合物通常如下制成,即,将化合物A与固体载体、液体载体等非活性载体混合,并根据需要添加表面活性剂、其他的制剂用辅助剂,制成乳剂、油剂、粉剂、粒剂、可湿性粉剂(日文原文:水和剤)、粒型可湿性粉剂(日文原文:顆粒水和剤)、流动剂(日文原文:フロアブル剤)、干流动剂(日文原文:ドライフロアブル剤)、微胶囊剂等制剂。
本发明的组合物通常含有0.0001~95重量%的化合物A。
作为制成制剂时使用的固体载体,例如可以举出粘土类(高岭土、硅藻土、膨润土、酸性白土等)、干式二氧化硅、湿式二氧化硅、滑石、陶瓷、其他无机矿物(绢云母、石英、硫、活性炭、碳酸钙等)、化学肥料(硫酸铵、磷酸铵、硝酸铵、尿素、氯化铵等)等的微粉末及粒状物等、以及合成树脂(聚丙烯、聚丙烯腈、聚甲基丙烯酸甲酯、聚对苯二甲酸乙二醇酯等聚酯树脂、尼龙-6、尼龙-11、尼龙-66等尼龙树脂、聚酰胺树脂、聚氯乙烯、聚偏二氯乙烯、氯乙烯-丙烯共聚物等)。
作为液体载体,例如可以举出水、醇类(甲醇、乙醇等)、酮类(丙酮、甲乙酮等)、芳香族烃类(甲苯、二甲苯等)、脂肪族烃类(己烷、环己烷等)、酯类(乙酸乙酯、乙酸丁酯等)、腈类(乙腈等)、醚类(二异丙醚、二乙二醇二甲醚等)、酰胺类(N,N-二甲基甲酰胺等)、亚砜类(二甲亚砜等)、以及植物油(大豆油、棉籽油等)。
作为表面活性剂,例如可以举出聚氧乙烯烷基醚、聚氧乙烯烷基芳基醚、聚乙二醇脂肪酸酯等非离子表面活性剂、以及烷基磺酸盐、烷基苯磺酸盐、烷基硫酸盐等阴离子表面活性剂。
作为其他的制剂用辅助剂,例如可以举出固着剂、分散剂、着色剂及稳定剂等,具体而言例如可以举出酪蛋白、明胶、糖类(淀粉、阿拉伯胶、纤维素衍生物、海藻酸等)、木质素衍生物、膨润土、合成水溶性高分子(聚乙烯醇、聚乙烯基吡咯烷酮、聚丙烯酸类等)、酸式磷酸异丙酯、2,6-二叔丁基-4-甲基苯酚、BHA(2-叔丁基-4-甲氧基苯酚与3-叔丁基-4-甲氧基苯酚的混合物)。
作为化合物A具有效力的有害节肢动物,例如可以举出以下的例子。
半翅目(Hemiptera):灰飞虱(Laodelphax striatellus)、褐飞虱(Nilaparvatalugens)、白背飞虱(Sogatella furcifera)、玉米花翅飞虱(Peregrinus maidis)、古北飞虱(Javesella pellucida)、甘蔗扁角飞虱(Perkinsiella saccharicida)、Tagosodesorizicolus等飞虱科(Delphacidae);黑尾叶蝉(Nephotettix cincticeps)、二点黑尾叶蝉(Nephotettix virescens)、二条斑黑尾叶蝉(Nephotettix nigropictus)、电光叶蝉(Recilia dorsalis)、小贯小绿叶蝉(Empoasca onukii)、马铃薯小绿叶蝉(Empoascafabae)、玉米黄翅叶蝉(Dalbulus maidis)、白翅褐脉叶蝉(Cofana spectra)等叶蝉科(Cicadellidae);吹泡虫(Mahanarva posticata)、甘蔗沫蝉(Mahanarva fimbriolata)等沫蝉科(Cercopidae);甜菜蚜(Aphis fabae)、大豆蚜(Aphis glycines)、棉蚜(Aphisgossypii)、苹果蚜(Aphis pomi)、绣线菊蚜(Aphis spiraecola)、桃蚜(Myzus persicae)、李短尾蚜(Brachycaudus helichrysi)、甘蓝蚜(Brevicoryne brassicae)、玫瑰苹果蚜(Dysaphis plantaginea)、菜缢管蚜(Lipaphis erysimi)、马铃薯长管蚜(Macrosiphumeuphorbiae)、茄沟无网蚜(Aulacorthum solani)、莴苣蚜(Nasonovia ribisnigri)、禾谷缢管蚜(Rhopalosiphum padi)、玉米蚜(Rhopalosiphum maidis)、橘蚜(Toxopteracitricida)、桃粉大尾蚜(Hyalopterus pruni)、高粱蚜(Melanaphis sacchari)、黑腹四脉绵蚜(Tetraneura nigriabdominalis)、甘蔗绵蚜(Ceratovacuna lanigera)、甘蔗绵蚜(Eriosoma lanigerum)等蚜科(Aphididae);葡萄根瘤蚜(Daktulosphaira vitifoliae)、美核桃根瘤蚜(Phylloxera devastatrix)、美核桃叶根瘤蚜(Phylloxera notabilis)、南方长山核桃叶根瘤蚜(Phylloxera russellae)等根瘤蚜科(Phylloxeridae);铁杉球蚜(Adelges tsugae)、冷杉球蚜(Adelges piceae)、冷杉球蚜(Aphrastasia pectinatae)等球蚜科(Adelgidae);稻黑蝽(Scotinophara lurida)、马来亚稻黑蝽(Scotinopharacoarctata)、黑须稻绿(Nezara antennata)、北二星蝽(Eysarcoris aeneus)、大刺白星蝽(Eysarcoris lewisi)、广二星蝽(Eysarcoris ventralis)、拟二星蝽(Eysarcorisannamita)、茶翅蝽(Halyomorpha halys)、稻绿蝽(Nezara viridula)、褐蝽象(Euschistusheros)、红带蝽象(Piezodorus guildinii)、稻蝽象(Oebalus pugnax)、椿虫(Dichelopsmelacanthus)等蝽科(Pentatomidae);掘地褐蝽(Scaptocoris castanea)等土蝽科(Cydnidae);点蜂缘蝽(Riptortus pedestris)、中稻缘蝽(Leptocorisa chinensis)、大稻缘蝽(Leptocorisa acuta)等蛛缘蝽科(Alydidae);稻棘缘蝽(Cletus punctiger)、叶足缘蝽(Leptoglossus australis)等缘蝽科(Coreidae);甘蔗长蝽(Cavereliussaccharivorus)、葫芦长蝽(Togo hemipterus)、麦长蝽(Blissus leucopterus)等长蝽科(Lygaeidae);赤须盲蝽(Trigonotylus caelestialium)、赤条纤盲蝽(Stenotusrubrovittatus)、二刺狭盲蝽(Stenodema calcarata)、美国牧草盲蝽(Lygus lineolaris)等盲蝽科(Miridae);温室粉虱(Trialeurodes vaporariorum)、烟粉虱(Bemisia tabaci)、柑橘粉虱(Dialeurodes citri)、黑刺粉虱(Aleurocanthus spiniferus)、山茶花黑刺粉虱(Aleurocanthus camelliae)、柃木裸粉虱(Pealius euryae)等粉虱科(Aleyrodidae);茶长本圆蚧(Abgrallaspis cyanophylli)、红圆蚧(Aonidiella aurantii)、梨圆蚧(Diaspidiotus perniciosus)、桑白蚧(Pseudaulacaspis pentagona)、矢尖盾蚧(Unaspisyanonensis)、柑桔尖盾蚧(Unaspis citri)等盾蚧科(Diaspididae);红蜡蚧(Ceroplastesrubens)等蚧科(Coccidae);吹绵蚧(Icerya purchasi)、银毛吹绵蚧(Iceryaseychellarum)等绵蚧科(Margarodidae);石蒜绵粉蚧(Phenacoccus solani)、扶桑绵粉蚧(Phenacoccus solenopsis)、日本臀纹粉蚧(Planococcus kraunhiae)、长尾粉蚧(Pseudococcus comstocki)、橘臀纹粉蚧(Planococcus citri)、柑栖粉蚧(Pseudococcuscalceolariae)、拟长尾粉蚧(Pseudococcus longispinus)、水稻粉红粉蚧(Brevenniarehi)等粉蚧科(Pseudococcidae);柑橘木虱(Diaphorina citri)、非洲木虱(Triozaerytreae)、欧洲梨木虱(Cacopsylla pyrisuga)、中国梨木虱(Cacopsylla chinensis)、马铃薯木虱(Bactericera cockerelli)、梨木虱(Cacopsylla pyricola)等木虱科(Psyllidae);悬铃木方翅网蝽(Corythucha ciliata)、菊方翅网蝽(Corythuchamarmorata)、梨冠网蝽(Stephanitis nashi)、杜鹃网蝽(Stephanitis pyrioides)等网蝽科(Tingidae);温带臭虫(Cimex lectularius)等臭虫科(Cimicidae);巨蝉(GiantCicada)(Quesada gigas)等蝉科(Cicadidae)及骚扰锥蝽(Triatoma infestans)等锥蝽属(Triatoma spp.)。
鳞翅目(Lepidoptera):二化螟(Chilo suppressalis)、台湾稻螟(Chilopolychrysus)、稻白螟(Scirpophaga innotata)、三化螟(Scirpophaga incertulas)、稻螟(Rupela albina)、稻纵卷叶螟(Cnaphalocrocis medinalis)、宽纹刷须野螟(Marasmiapatnalis)、稻显纹纵卷叶螟(Marasmia exigua)、棉卷叶螟(Notarcha derogata)、亚洲玉米螟(Ostrinia furnacalis)、欧洲玉米螟(Ostrinia nubilalis)、菜螟(Hellulaundalis)、葡萄切叶野螟(Herpetogramma luctuosale)、蓝草螟蛾(Pediasiateterrellus)、稻三点螟(Nymphula depunctalis)、甘蔗螟(Diatraea saccharalis)等草螟科(Crambidae);小玉米螟(Elasmopalpus lignosellus)、印度谷蛾(Plodiainterpunctella)、皮暗斑螟(Euzophera batangensis)等螟蛾科(Pyralidae);斜纹夜蛾(Spodoptera litura)、甜菜夜蛾(Spodoptera exigua)、粘虫(Mythimna separata)、甘蓝夜蛾(Mamestra brassicae)、大螟(Sesamia inferens)、灰翅夜蛾(Spodopteramauritia)、稻螟蛉(Naranga aenescens)、草地夜蛾(Spodoptera frugiperda)、莎草粘虫(Spodoptera exempta)、小地老虎(Agrotis ipsilon)、黑点银纹夜蛾(Autographanigrisigna)、金斑夜蛾(Plusia festucae)、黄豆银纹夜蛾(Chrysodeixis includens)、粉纹夜蛾属(Trichoplusia spp.)、烟芽夜蛾(Heliothis virescens)等实夜蛾属(Heliothisspp.)、棉铃虫(Helicoverpa armigera)、谷实夜蛾(Helicoverpa zea)等铃夜蛾属(Helicoverpa spp.)、黎豆夜蛾(Anticarsia gemmatalis)、棉叶波纹夜蛾(Alabamaargillacea)、啤酒花藤蛀虫(Hop vine borer)(Hydraecia immanis)等夜蛾科(Noctuidae);菜粉蝶(Pieris rapae)等粉蝶科(Pieridae);梨小食心虫(Grapholitamolesta)、沙果小食心虫(Grapholita dimorpha)、大豆食心虫(Leguminivoraglycinivorella)、日豆小卷蛾(Matsumuraeses azukivora)、苹果小卷叶蛾(Adoxophyesorana fasciata)、茶小卷叶蛾(Adoxophyes honmai)、茶长卷蛾(Homona magnanima)、苹果黄卷蛾(Archips fuscocupreanus)、苹果小卷蛾(Cydia pomonella)、黄螟(Tetramoeraschistaceana)、菜豆小卷蛾(Bean Shoot Borer)(Epinotia aporema)、绒花小卷蛾(Citrus fruit borer)(Ecdytolopha aurantiana)等卷蛾科(Tortricidae);茶细蛾(Caloptilia theivora)、金纹细蛾(Phyllonorycter ringoniella)等细蛾科(Gracillariidae);桃柱果蛾(Carposina sasakii)等果蛀蛾科(Carposinidae);咖啡潜叶蛾(Leucoptera coffeella)、桃潜叶蛾(Lyonetia clerkella)、银纹潜叶蛾(Lyonetiaprunifoliella)等潜蛾科(Lyonetiidae);舞毒蛾(Lymantria dispar)等毒蛾属(Lymantria spp.)、茶毒蛾(Euproctis pseudoconspersa)等黄毒蛾属(Euproctis spp.)等毒蛾科(Lymantriidae);小菜蛾(Plutella xylostella)等菜蛾科(Plutellidae);桃枝麦蛾(Anarsia lineatella)、甘薯阳麦蛾(Helcystogramma triannulella)、红铃麦蛾(Pectinophora gossypiella)、马铃薯麦蛾(Phthorimaea operculella)、番茄麦蛾(Tutaabsoluta)等麦蛾科(Gelechiidae);美国白蛾(Hyphantria cunea)等灯蛾科(Arctiidae);甘蔗大螟(Telchin licus)等蝶蛾科(Castniidae);芳香木蠹蛾(Cossus insularis)等木蠹蛾科(Cossidae);大造桥虫(Ascotis selenaria)等尺蛾科(Geometridae);丽绿刺蛾(Parasa lepida)等刺蛾科(Limacodidae);柿展足蛾(Stathmopoda masinissa)等展足蛾科(Stathmopodidae);鬼脸天蛾(Acherontia lachesis)等天蛾科(Sphingidae);Nokonaferalis、苹果透翅蛾(Synanthedon hector)、苹果透翅蛾(Synanthedon tenuis)等透翅蛾科(Sesiidae);直纹稻弄蝶(Parnara guttata)等弄蝶科(Hesperiidae)、衣蛾(Tineatranslucens)、幕谷蛾(Tineola bisselliella)等谷蛾科(Tinedae)。
缨翅目(Thysanoptera):西花蓟马(Frankliniella occidentalis)、棕榈蓟马(Thrips palmi)、茶黄硬蓟马(Scirtothrips dorsalis)、烟蓟马(Thrips tabaci)、花蓟马(Frankliniella intonsa)、稻蓟马(Stenchaetothrips biformis)、美洲棘蓟马(Echinothrips americanus)等蓟马科(Thripidae);稻管蓟马(Haplothrips aculeatus)等管蓟马科(Phlaeothripidae)。
本发明的有害节肢动物的防除方法中,将化合物A的有效量直接施用于有害节肢动物、并且/或者施用于有害节肢动物的栖息场所(植物或土壤)。
对于化合物A的施用量而言,在每10000m2中通常为1~10000g。在化合物A被制成乳剂、可湿性粉剂、流动剂等制剂的情况下,通常以使有效成分浓度为0.01~10000ppm的方式用水稀释后施用,粒剂、粉剂等通常直接施用。
另外,本发明的组合物可以作为旱田、水田、草坪、果树园等农耕地中的有害节肢动物的防除剂使用。
实施例
以下,利用制造例及试验例等对本发明进一步详细说明,然而本发明并不仅限定于这些例子。
给出化合物A的制造例。
向利用美国专利第6537948号说明书中记载的方法制造出的(3-{2-氯-4-氟-5-[3-甲基-2,6-二氧代-4-(三氟甲基)-1,2,3,6-四氢嘧啶-1-基]苯氧基}-2-吡啶基氧基)乙酸2.00g、二甲苯8.01g与三氟化硼乙醚络合物0.05g的混合物中,在50℃滴加40%重氮乙酸乙酯二甲苯溶液1.61g,搅拌4小时。向所得的混合物中再加入三氟化硼乙醚络合物0.05g及40%重氮乙酸乙酯二甲苯溶液1.94g,在50℃搅拌1小时。将所得的混合物自然冷却到室温为止后,加入10%硫酸水溶液,用乙酸乙酯进行萃取。用饱和碳酸氢钠溶液清洗所得的有机层,在减压下进行浓缩。对所得的残渣实施硅胶层析,得到1.01g的化合物A。
将化合物A的1H-NMR数据表示如下。
1H-NMR(CDCl3)δ(ppm):7.94-7.92(1H,m),7.37(1H,d,J=9.1Hz),7.33-7.30(1H,m),6.96-6.91(1H,m),6.89(1H,d,J=6.6Hz),6.29(1H,s),5.12-4.99(2H,m),4.63(2H,s),4.20(2H,q,J=7.1Hz),3.51(3H,s),1.27(3H,t,J=7.1Hz).
下面利用试验例来显示出化合物A对于有害节肢动物的效力。需要说明的是,份表示重量份。
试验例1
将聚氧乙烯烷基醚硫酸铵盐与湿式二氧化硅的混合物(重量比1:1)35份、化合物A20份、和水45份充分地混合。将所得的混合物用含有シンダイン(注册商标)0.03体积%的水稀释,制备出含有500ppm的化合物A的稀释液。向种植于容器中的卷心菜(Brassicaeoleracea)苗(第2~3片真叶展开期)的叶子以20mL/苗的比例散布该稀释液。其后,切取该苗的茎叶部,将该叶子放入铺设有滤纸的容器内。向其中投放5只小菜蛾2龄幼虫,在25℃静置5天后,计数生存虫数,利用下式求出死虫率,其结果为,死虫率为100%。
死虫率(%)=(1-生存虫数/5)×100
比较试验例1
取代化合物A而使用化合物B,依照试验例1进行试验,其结果是,死虫率为0%。
产业上的可利用性
化合物A对有害节肢动物显示出优异的防除效果。
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JP2001348376A (ja) * | 2000-06-07 | 2001-12-18 | Sumitomo Chem Co Ltd | ウラシル化合物およびその用途 |
WO2011137088A1 (en) * | 2010-04-27 | 2011-11-03 | E. I. Du Pont De Nemours And Company | Herbicidal uracils |
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JPH03287578A (ja) * | 1990-01-18 | 1991-12-18 | Nissan Chem Ind Ltd | ウラシル誘導体及び有害生物防除剤 |
JPH06510992A (ja) * | 1991-09-20 | 1994-12-08 | ビーエーエスエフ アクチェンゲゼルシャフト | 置換3−フェニルウラシル |
JP2001348376A (ja) * | 2000-06-07 | 2001-12-18 | Sumitomo Chem Co Ltd | ウラシル化合物およびその用途 |
WO2011137088A1 (en) * | 2010-04-27 | 2011-11-03 | E. I. Du Pont De Nemours And Company | Herbicidal uracils |
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