TWI827660B - 聯吡啶化合物及其用途 - Google Patents
聯吡啶化合物及其用途 Download PDFInfo
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- TWI827660B TWI827660B TW108131889A TW108131889A TWI827660B TW I827660 B TWI827660 B TW I827660B TW 108131889 A TW108131889 A TW 108131889A TW 108131889 A TW108131889 A TW 108131889A TW I827660 B TWI827660 B TW I827660B
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- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
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- Plural Heterocyclic Compounds (AREA)
Abstract
本發明係提供一種對植物病害具有優異的防除效力之化合物。下述式(A)所示之化合物係對植物病害具有優異的防除效力。
Description
本申請係主張於2018年9月13日所申請之日本國專利申請第2018-171185號的優先權及其利益者,藉由參照其全部內容而引入於本申請中。
本發明係關於聯吡啶化合物及其用途。
先前,為了防除植物病害已開發出各種化合物,並供應於實用(參照非專利文獻1)。
[非專利文獻1]The Pesticide Manual - 17th edition (BCPC刊) ISBN 978-1-901396-88-1
本發明係以提供一種對植物病害具有優異的防除效力之化合物為課題。
本發明係如下所述。
[1]一種下述式(A)所示之化合物(以下,亦記載為化合物A)
[2]一種組成物,該組成物含有[1]所記載之化合物、及不活性載體。
[3]一種植物病害之防除方法,該防除方法係藉由對植物或土壤以有效量的[1]所記載之化合物進行處理。
藉由本發明可防除植物病害。
本發明之組成物係含有化合物A及不活性載體。本發明之組成物通常係將化合物A與固體載體、液體載體等不活性載體混合,並且因應所需添加界面活性劑、其他製劑用補助劑,而製劑化成乳劑、油劑、粉劑、粒劑、水和劑、顆粒水和劑、懸浮劑(Flowable)、乾懸浮劑、微膠囊劑等。
本發明之組成物通常含有0.0001至95重量%的化合物A。
製劑化時所使用的固體載體可列舉例如:黏土類(高嶺土、矽藻土、皂土、酸性白土等)、乾式氧化矽、溼式氧化矽、滑石、陶瓷、其他無機礦物(絹雲母、石英、硫黃、活性碳、碳酸鈣等)、化學肥料(硫酸銨、磷酸銨、硝酸銨、尿素、氯化銨等)等微粉末及粒狀物等、以及合成樹脂(聚丙烯、聚丙烯腈、
聚甲基丙烯酸甲酯、聚對苯二甲酸乙二酯等聚酯樹脂、尼龍-6、尼龍-11、尼龍-66等尼龍樹脂、聚醯胺樹脂、聚氯乙烯、聚偏二氯乙烯、氯乙烯-丙烯共聚物等)。
液體載體可列舉例如:水、醇類(甲醇、乙醇等)、酮類(丙酮、甲基乙基酮等)、芳香族烴類(甲苯、二甲苯等)、脂肪族烴類(己烷、環己烷等)、酯類(乙酸乙酯、乙酸丁酯等)、腈類(乙腈等)、醚類(二異丙基醚、二乙二醇二甲基醚等)、醯胺類(N,N-二甲基甲醯胺等)、亞碸類(二甲亞碸等)、及植物油(大豆油、棉籽油等)。
界面活性劑可列舉例如: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離子界面活性劑、及烷基磺酸鹽、烷基苯磺酸鹽、烷基硫酸鹽等陰離子界面活性劑。
其他製劑用補助劑可舉出固著劑、分散劑、著色劑及穩定劑等,具體的而言,可列舉例如:酪蛋白、明膠、糖類(澱粉、阿拉伯膠、纖維素衍生物、海藻酸等)、木質素衍生物、皂土、合成水溶性高分子(聚乙烯醇、聚乙烯吡咯烷酮、聚丙烯酸類等)、酸性磷酸異丙酯、2,6-二-第三丁基-4-甲苯酚、BHA(2-第三丁基-4-甲氧苯酚及3-第三丁基-4-甲氧苯酚之混合物)。
化合物A係對植物病原性微生物具有效力。源自植物病原性微生物之植物病害可舉出下列者。括弧內表示引起該病害之病原性微生物的學名。
水稻之稻熱病(Magnaporthe grisea)、胡麻葉枯病(Cochliobolus miyabeanus)、紋枯病(Rhizoctonia solani)、稻苗徒長病(Gibberella fujikuroi)、黃化萎縮病(Sclerophthora macrospora);小麥之白粉病(Blumeria graminis)、赤黴病(Fusarium graminearum、Fusarium avenaceum、Fusarium culmorum、Microdochium nivale)、黃銹病(Puccinia striiformis)、黑銹病(Puccinia graminis)、赤銹病(Puccinia recondita)、紅色雪腐病(Microdochium nivale、Microdochium majus)、雪腐小球菌核病(Typhula incarnata、Typhula ishikariensis)、裸黑穗病(Ustilago tritici)、腥黑穗
病(Tilletia caries、Tilletia controversa)、眼點病(Pseudocercosporella herpotrichoides)、葉枯病(Stagonospora nodorum)、黃斑病(Pyrenophoratritici-repentis)、立枯絲核菌引起之苗立枯病(Rhizoctonia solani)、立枯病(Gaeumannomyces graminis);大麥之白粉病(Blumeria graminis)、赤黴病(Fusarium graminearum、Fusarium avenaceum、Fusarium culmorum、Microdochium nivale)、黃銹病(Puccinia striiformis)、黑銹病(Puccinia graminis)、赤銹病(Puccinia hordei)、葉銹病(Puccinia hordei)、裸黑穗病(Ustilago nuda)、雲紋葉枯病(Rhynchosporium secalis)、網斑病(Pyrenophora teres)、斑點病(Cochliobolus sativus)、斑葉病(Pyrenophora graminea)、隔孢葉斑病(Ramularia collo-cygni)、立枯絲核菌引起之苗立枯病(Rhizoctonia solani);玉米之銹病(Puccinia sorghi)、南方銹病(Puccinia polysora)、大斑病(Setosphaeria turcica)、熱帶性銹病(Physopella zeae)、胡麻葉枯病(Cochliobolus heterostrophus)、炭疽病(Colletotrichum graminicola)、灰色葉斑病(Cercospora zeae-maydis)、褐斑病(Kabatiella zeae)、暗球腔菌葉斑病(Phaeosphaeria maydis)、Stenocarpella maydis、Stenocarpclla macrospora、鐮刀菌枯萎病(Fusarium graminearum、Fusarium verticilioides、Colletotrichum graminicola)、黑穗病(Ustilago maydis);棉花之炭疽病(Colletotrichum gossypii)、白斑病(Ramularia areola)、黑斑病(Alternaria macrospora、Alternaria gossypii)、根串珠黴(Thielaviopsis)屬菌引起之黑根腐(Black root rot)病(Thielaviopsis basicola);咖啡之銹病(Hemileia vastatrix)、葉斑病(Cercospora coffeicola);油菜籽之菌核病(Sclerotinia sclerotiorum)、黑斑病(Alternaria brassicae)、根腐病(Phoma lingam);甘蔗之銹病(Puccinia melanocephela、Puccinia kuehnii);向日葵銹病(Puccinia helianthi)、露菌病(Plasmopara halstedii);柑橘類之黑點病(Diaporthe citri)、瘡痂病(Elsinoe fawcetti)、果實腐敗病(Penicillium digitatum、Penicillium italicum)、疫病(Phytophthora parasitica、Phytophthora citrophthora);蘋果之花腐病(Monilinia mali)、腐爛病(Valsa ceratosperma)、白粉病
(Podosphaera leucotricha)、斑點落葉病(Alternaria alternata apple pathotype)、黑星病(Venturia inaequalis)、炭疽病(Glomerella cingulata)、褐斑病(Diplocarpon mali)、輪紋病(Botryosphaeria berengeriana)、疫病(Phytophtora cactorum);梨子之黑星病(Venturia nashicola、Venturia pirina)、黑斑病(Alternaria altemata Japanese pear pathotype)、赤星病(Gymnosporangium haraeanum);桃子之褐腐病(Monilinia fructicola)、黑星病(Cladosporium carpophilum)、果實腐敗病(Phomopsis sp.);葡萄之黑痘病(Elsinoe ampelina)、晚腐病(Glomerella cingulata)、白粉病(Uncinula necator)、銹病(Phakopsora ampelopsidis)、黑腐病(Guignardia bidwellii)、露菌病(Plasmopara viticola);柿子之炭疽病(Gloeosporium kaki)、落葉病(Cercospora kaki、Mycosphaerella nawae);瓜類之炭疽病(Colletotrichum lagenarium)、白粉病(Sphaerotheca fuliginea)、蔓枯病(Didymella bryoniae)、褐斑病(Corynespora cassiicola)、蔓割病(Fusarium oxysporum)、露菌病(Pseudoperonospora cubensis)、疫病(Phytophthora sp.)、苗立枯病(Pythium sp.);番茄之輪紋病(Alternaria solani)、葉黴病(Cladosporium fulvum)、黑黴病(Pseudocercospora fuligena)、疫病(Phytophthora infestans)、白粉病(Leveillula taurica);茄子之褐紋病(Phomopsis vexans)、白粉病(Erysiphe cichoracearum);十字花科蔬菜之黑斑病(Alternaria japonica)、白斑病(Cercosporella brassicae)、根瘤病(Plasmodiophora brassicae)、露菌病(Peronospora parasitica);蔥之銹病(Puccinia allii);大豆之紫斑病(Cereosporakikuchii)、黑痘病(Elsinoe glycines)、黑點病(Diaporthe phaseolorum var.sojae)、銹病(Phakopsora pachyrhizi)、褐色輪紋病(Corynespora cassiicola)、炭疽病(Colletotrichum glycines、Colletotrichum truncatum)、葉腐病(Rhizoctonia solani)、褐紋病(Septoria glycines)、斑點病(Cercospora sojina)、菌核病(Sclerotinia sclerotiorum)、白粉病(Microsphaera diffusa)、疫黴根腐病(Phytophthora sojae)、露菌病(Peronospora manshurica)、猝死病(Fusarium virguliforme);四季豆之菌核病
(Sclerotinia sclerotiorum)、銹病(Uromyces appendiculatus)、角斑病(Phaeoisariopsis griseola)、炭疽病(Colletotrichum lindemuthianum);落花生之黑澀病(Cercospora personata)、褐斑病(Cercospora arachidicola)、白絹病(Sclerotium rolfsii);碗豆之白粉病(Erysiphe pisi);馬鈴薯之早疫病(Alternaria solani)、疫病(Phytophthora infestans)、粉紅腐爛病(Pink rot)(Phytophthora erythroseptica)、粉狀瘡痂病(Spongospora subterranean f.sp.subterranea)、半身萎凋病(Verticillium albo-atrum、Verticillium dahliae、Verticillium nigrescens);草莓之白粉病(Sphaerotheca humuli);茶網餅病(Exobasidium reticulatum)、白星病(Elsinoe leucospila)、輪斑病(Pestalotiopsis sp.)、炭疽病(Colletotrichum theae-sinensis);菸草之赤星病(Alternaria longipes)、炭疽病(Colletotrichum tabacum)、露菌病(Peronospora tabacina)、疫病(Phytophthora nicotianae);甜菜之褐斑病(Cercospora beticola)、葉腐病(Thanatephorus cucumeris)、根腐病(Thanatephorus cucumeris)、黑根病(Aphanomyces cochlioides)、銹病(Uromyces betae);玫瑰之黑星病(Diplocarpon rosae)、白粉病(Sphaerotheca pannosa);菊花之褐斑病(Septoria chrysanthemi-indici)、白銹病(Puccinia horiana);洋蔥之白斑葉枯病(Botrytis cinerea、Botrytis byssoidea、Botrytis squamosa)、灰色腐敗病(Botrytis allii)、小菌核性腐敗病(Botrytis squamosa);各種作物之菌核病(Sclerotinia sclerotiorum);蘿蔔黑斑病(Alternaria brassicicola);草坪之錢幣斑病(Sclerotinia homoeocarpa)、草坪之葉腐病及巨斑病(Rhizoctonia solani);以及香蕉之葉斑病(Mycosphaerella tijiensis、Mycosphaerella musicola)。
由麴菌(Aspergillus)屬、青黴菌(Penicillium)屬、鐮菌(Fusarium)屬、赤黴菌(Gibberella)屬、木黴菌(Tricoderma)屬、根串珠黴(Thielaviopsis)屬、根黴菌(Rhizopus)屬、毛黴(Mucor)屬、皮殼菌(Corticium)屬、桑胴枯病菌(Phoma)屬、立枯絲核菌(Rhizoctonia)屬、及二孢菌(Diplodia)屬菌等所引起之各種作物的種子病
害或生育初期病害。由多黏梭菌(Polymixa)屬或油壺菌(Olpidium)屬等為媒介之各種作物的病毒病。
水稻之苗立枯細菌病(Burkholderia plantarii);黃瓜之斑點細菌病(Pseudomonas syringae pv.lachrymans);茄子之青枯病(Ralstonia solanacearum),柑橘之潰瘍病(Xanthomonas citiri);大白菜之軟腐病(Erwinia carotovora)等。
本發明之植物病害的防除方法可列舉例如:莖葉散布、種子消毒等對植物體之處理;土壤處理等對植物栽培地之處理。
化合物A之處理量係每1000m2通常為1至10000g。化合物A製劑化成乳劑、水和劑、懸浮劑等時,通常,以使有效成分濃度成為0.01至10000ppm之方式用水稀釋後施用;粒劑、粉劑等時通常直接施用。
本發明之組成物係可使用作為旱田、水田、草坪、果樹園等之農耕地中的植物病害之防除劑。
以下,將本發明藉由製造例及試驗例更詳細地說明,惟,本發明並非僅限定於該等例者。
首先,顯示化合物A之製造例。
第1步驟
在氮環境下,100mL高壓釜中添加以美國專利第9850209號說明書所記載之方法製造出的6-氯-3-(乙磺醯基)吡啶-2-羧酸8.58g、甲醇25.3g、碳酸氫鉀6.98g,及5%Pd/碳0.22g,密閉後,在氫環境下反應45小時。將所得之混合物過濾,將過濾物依序以甲醇及水洗淨。在所得之水洗淨液中添加35%鹽酸進行中和。將所得之固體過濾,以水洗淨並乾燥後,獲得0.32g之下述式所示之中間物A。
中間物A:1H-NMR(DMSO-d6)δ(ppm):14.40(2H,s),8.72(2H,d),8.59(2H,d),3.61(4H,q),1.21(6H,t).
第2步驟
在亞硫醯氯1.39g、二甲苯49.72g、及N,N-二甲基甲醯胺0.04g之混合物中,以60℃添加3.79g的中間物A及二甲苯5.52g之混合物,以60℃攪拌5.5小時間。在所得之混合物中添加亞硫醯氯2.84g,以60℃攪拌7小時。使所得之混合物成為室溫後,減壓下進行濃縮。將所得之殘餘物添加至以美國專利第8426443號說明書所記載之方法製造出的2-胺基-4-(三氟甲磺醯基)酚4.20g及四氫呋喃12.54g之混合物中,接著,依序添加四氫呋喃35.10g及二甲苯34.11g,以60℃攪拌2小時。在所得之混合物中以60℃添加水24.94g、四氫呋喃19.36g及27%氫氧化鈉水溶液1.88g之混合物,調整成pH 5.3。將所得之混合物冷卻至5℃,將所得之結晶過濾。將過濾物依序以水、二甲苯及50%二甲苯/四氫呋喃溶液洗淨並乾燥後,獲得6.35g之下述式所示之中間物B。
中間物B:1H-NMR(DMSO-d6)δ(ppm):12.31(2H,br s),10.65(2H,s),8.90(2H,d),8.78(2H,d),8.61(2H,d),7.84(2H,dd),7.32(2H,d),3.67(4H,q),1.22(6H,t).
第3步驟
將3.08g之中間物B、二甲苯335g及p-甲苯磺酸一水和物33.71g之混合物在迴流下,使用迪安-斯塔克(Dean Stark)裝置一邊將生成之水排除至系統外一邊攪拌69小時。將所得之混合物冷卻至100℃後,添加至室溫的20%碳酸鉀水溶液92.5g,以80℃攪拌。過濾析出之固體,將過濾物依序以水及二甲苯洗淨並乾燥。將所得之固體以室溫溶解於N,N-二甲基甲醯胺1000g後,將水100g滴下。將所得之固體過濾,過濾物依序以N,N-二甲基甲醯胺及水洗淨並乾燥後,獲得0.83g之化合物A。
化合物A之1H-NMR數據如下所示。
1H-NMR(N,N-二甲基甲醯胺-d7)δ(ppm):9.11(2H,d),8.95(2H,d),8.93(2H,d),8.55(2H,d),8.46(2H,dd),4.04(4H,q),1.40(6H,m).
接著,顯示試驗例。
試驗例1
在塑膠罐中充塞土壤,並在此中播種番茄(品種:Patio),在溫室內栽培19天。將聚氧乙烯烷基醚硫酸銨鹽與溼式氧化矽之混合物(重量比1:1)35重量份、化合物A20重量份及水45重量份充分地混合。將所得之混合物以水稀釋後,調製成含有125ppm之化合物A的稀釋液。將此稀釋液以充分地附著於上述番茄葉面之方式進行散布。將散布後之番茄風乾,1天後噴霧接種含有番茄輪紋病菌(細胞色素b之第129號胺基酸殘基從苯丙胺酸置換成白胺酸之番茄輪紋病菌(Alternaria solani))胞子的水懸浮液。之後,將番茄在15℃多溼下靜置6天,調查病斑面積。結果,經化合物A處理之番茄中的病斑面積,係無處理之番茄中的病斑面積的0%。此外,所謂無處理意指沒有散布上述稀釋液。
化合物A係對植物病害顯示優異的防除效果。
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