TWI647219B - 經取代之吡唑吡唑衍生物及其作爲除草劑的用途 - Google Patents
經取代之吡唑吡唑衍生物及其作爲除草劑的用途 Download PDFInfo
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- TWI647219B TWI647219B TW103127424A TW103127424A TWI647219B TW I647219 B TWI647219 B TW I647219B TW 103127424 A TW103127424 A TW 103127424A TW 103127424 A TW103127424 A TW 103127424A TW I647219 B TWI647219 B TW I647219B
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Abstract
本發明之課題係提供可有效果地防治實用上成為問題之較高葉齡的重要雜草的化合物。
本發明之解決手段係揭示可解決上述課題的特定吡唑吡唑衍生物。
Description
本發明係關於經取代之吡唑吡唑衍生物及該化合物作為除草劑的利用。
近年來，對於農作物之栽培，使用許多的除草劑而有助於農作業之省力化或農作物之生產性提升。於旱田‧水稻栽培已有許多除草劑被實用化。
然而，雜草之種類繁多，又各種雜草的發芽及生長時期不同，再者，多年生雜草的發生為長期的。因此以一次除草劑噴灑來防治所有雜草是非常困難的。
水稻的初中期單次處理劑在稗草(稻稗(Echinochloa oryzicola)、野稗(Echinochloa crus-galli var.crus-galli)、台灣野稗(Echinochloa crus-galli var.formosensis)、細葉旱稗(Echinochloa crus-galli var.praticola)、長毛野稗(Echinochloa crus-galli var.caudata)之總稱)至2~3葉期為止的處理顯示為有效的，可以一次之處理而防治主要雜草(參考非專利文獻1)。然而，對於已實用化的初中期單次處理劑，要防治稗草已生長至3.5葉期以上的時期之雜草係非常困難的，對稗草之3葉期時的防治及3.5葉期時的防治於技術上有很大的隔絶。
再者歷經長期的除草效果之維持(殘效性)，於農藥噴灑的減低、作業的省力化、成本削減的面向上成為重要的，被視為是初中期單次處理劑所必要的性能。
又，近年來ALS(乙醯乳酸合成酶(acetolactate synthase))抑制劑廣泛普及，對ALS抑制劑有抵抗性的雜草成為問題。尤其，對多年生的野慈菇(Sagittaria trifolia)或矮慈菇(Sagittaria pygmaea)之抗ALS抑制劑性生物型具有充分的效果的除草劑少。又，就近年成為問題的雜草而言，多年生中可列舉野荸薺(Eleocharis kuroguwai)、扁秆藨草(Scirpus planiculmis)、三江藨草(Scirpus nipponicus)等，一年生中可列舉合萌(Aeschynomene indica)、千金子(Leptochloa chinensis)、疣草(Murdannia keisak)等，對此等難防治雜草具有充分效果的除草劑少。
另一方面，許多吡唑衍生物被廣泛使用作為除草劑而實用化，例如，4-(2,4-二氯苯甲醯基)-1,3-二甲基-5-吡唑基p-甲苯磺酸酯(一般名：「吡唑特(pyrazolate)」)、2-[4-(2,4-二氯苯甲醯基)-1,3-二甲基吡唑-5-基氧基]苯乙酮(一般名：「普芬草(pyrazoxyfen)」)、2-[4-(2,4-二氯-m-甲苯甲醯基(toluoyl))-1,3-二甲基吡唑-5-基氧基]-4’-甲基苯乙酮(一般名：「吡草酮(benzofenap)」)等，但任一者之單劑皆於日本註冊上對稗草的適用範圍係至1.5葉期為止，此等之吡唑衍生物係對廣範圍的雜草為有效，但對高葉齡的稗草的效果未必充分。
又，專利文獻1所記載的實施例4.73之化合物的1-(3-氯-4,5,6,7-四氫吡唑并[1,5-a]吡啶-2-基)-5-[甲基(丙-2-炔基)胺基]吡唑-4-甲腈(一般名：「雙唑草腈(pyraclonil)」，商品名pyraclon)係對廣範圍的雜草為有效，但對高葉齡之稗草的效果並不充分，於日本之註冊上的本劑單劑之對稗草的適用範圍係至1.5葉期為止。
專利文獻1 WO94/08999
非專利文獻1 水田雜草之生態及其防治-水稻作之雜草與除草劑解說-159頁
本發明之目的係提供具有廣範圍的殺草譜(weeding spectrum)，可防治實用上成為問題之更高葉齡的重要雜草，且對水稻等作物不會產生藥害的除草劑組成物。
本發明者們為了達成前述目的，不斷專心研究的結果，發現具有特定化學構造的吡唑吡唑衍生物係
經歷長期間具有寬廣的殺草譜的同時，對高葉齡之重要雜草呈現優異的除草效力，另一方面，對栽培作物具有充分的安全性，基於如此見識而完成本發明。據此，本發明係提供下述式(I)所示的化合物之吡唑吡唑衍生物。
上式中，R1表示鹵素原子，R2表示氰基、硝基，R3表示氫原子、三氟乙醯基、五氟丙醯基、七氟丁烯基，R4~R6可相同或相異，表示氫原子、鹵素原子、(依情形經1個或以上之鹵素原子取代的)C1~C6烷基、(依情形經1個或以上之鹵素原子取代的)C3~C6環烷基、(依情形經1個或以上之鹵素原子取代的)C1~C6烷氧基(C1~C6)烷基、或者(依情形經1個或以上之鹵素原子、硝基、氰基、(依情形經1個或以上之鹵素原子取代的)C1~C4烷基或C1~C4烷氧基所取代的)苯基，a表示3~5，且b表示0~2，(惟，R1為氯原子、R2為氰基、R3~R6為氫原子、b為1所表示的化合物除外)。
式(I)中，較佳係：R1表示氯原子、溴原子，R4~R6可相同或相異，表示氫原子、鹵素原子、(依情形經1個或以上之鹵素原子取代的)C1~C6烷基、C3~C6環烷基、C3~C6烷氧基(C1~C6)烷基、苯基，且a表示4。
式(I)中，更佳係：R1表示氯原子，R2表示氰基，R4~R6可相同或相異，表示氫原子、鹵素原子、(依情形經1個或以上之鹵素原子取代的)C1~C6烷基，且b表示1。
於本說明書，如各取代基前面的「Ca~Cb」之記載，各自意指該基中碳原子存有a個~b個。
「鹵素原子」係包含氟、氯、溴及碘原子。
「烷基」可為直鏈狀或支鏈狀，並未限定，但可列舉例如，甲基、乙基、正-或異-丙基、正-、異-、二級-或三級-丁基、正-戊基、正-己基等，係於各自指定的碳原子數的範圍內選擇。
「烷氧基」意指烷基部分具有上述意義的烷基-O-基，並未限定，但例如可列舉甲氧基、乙氧基、正-或異-丙氧基、正-、異-、二級-或三級-丁氧基等，係於各自指定的碳原子數的範圍內選擇。
「環烷基」並未限定，但包含環丙基、環丁基、環戊基、環己基等，係於各自指定的碳原子數的範圍內選擇。
「烷基」、「烷氧基」、「環烷基」此等基所含的氫原子之至少1個可經鹵素原子取代，例如列舉烷基為例時，雖未限定，但可為氯甲基、二氯甲基、三氟甲基、氯乙基、二氯乙基、三氟乙基、四氟丙基、溴乙基、溴丙基、氯丁基、氯己基、全氟己基，係於各自指定的碳原子數的範圍內選擇。
前述之基或部分經鹵素原子多取代、或苯基經鹵素原子、硝基、氰基、(依情形經1個或以上之鹵素原子取代的)C1~C4烷基或C1~C4烷氧基多取代的情形，此基可以多於1個的相同或相異的鹵素原子及/或取代基取代。
又，幾何異構物存在的情形，包含順式體及反式體。又本發明亦關於包含於式(I)所示的化合物但未具體定義的全部幾何異構物及彼等之混合物。
於以下列舉的全部式，取代基及記號，除非另有定義，具有與式(I)定義者相同意義。依據本發明所提供的式(I)之化合物中R3為氫原子者可藉由式(II)所示的化合物之烷基化反應而簡便地合成，
R3不含氫原子的化合物可接著藉由式(III)之全氟醯胺化反應而合成：
式(II)之化合物係依據WO93/10100及WO94/08999所記載的方法，可藉由四氫-2H-吡喃-2-亞基乙腈或5-氯戊醯氯而合成。
式(II)之化合物之烷基化反應，其本身可參考周知反應條件而合成(例如，WO94/08999)。依情形，可以所謂將胺基保護、烷基化、脫保護的流程進行。
式(III)之全氟醯胺化反應，其本身可藉由周知反應條件及其引用的文獻所記載的周知方法而容易地製造(例如日本特開2005-154420)。
依據本發明所提供的式(I)之化合物係如由後述的試驗例1~3所記載的除草活性試驗之結果所示，具有優異的除草效果，有用於作為除草劑。
本發明之式(I)之化合物係對多種農耕地雜草及非農耕地雜草具有活性。就栽培植物而言，例如可列
舉稻、小麥、大麥、玉米、燕麥、高粱等之禾本科植物；大豆、棉、甜菜、向日癸、油菜子等之闊葉作物之外，果樹、果菜類或根菜類、葉菜類等之蔬菜、草坪等，可使用於彼等之栽培。
本發明之化合物係對下列列舉水田中成為問題的各種雜草，於注水(flooding)或未注水的狀態下的土壤處理、土壤混和處理及莖葉處理之任一處理方法皆具有除草效力。以下例示該雜草，但並未限定於此等例。
就可藉由本發明之式(I)之化合物而防治的水田雜草而言，例如，可列舉窄葉澤瀉(Alisma canaliculatum)、野慈菇(Sagittaria trifolia)、矮慈菇(Sagittaria pygmaea)等之澤瀉科雜草；異花莎草(Cyperus difformis)、水莎草(Cyperus serotinus)、螢藺(Scirpus juncoides)、野荸薺(Eleocharis kuroguwai)、扁秆藨草(Scirpus planiculmis)、三江藨草(Scirpus nipponicus)等之莎草科雜草；陌上草(Lindernia procumbens)、北美母草杜比亞亞種(Lindernia dubia subsp.dubia)、美洲母草(Lindernia dubia)等之玄參科雜草；鴨舌草(Monochoria vaginalis)、雨久花(Monochoria korsakowii)等之雨久花科雜草；異匙葉藻(Potamogeton distinctus)等之眼子菜科雜草；節節菜(Rotala indica)、多花水莧(Ammannia multiflora)等之千屈菜科雜草；狼把草(Bidens tripartita)、大狼把草(Bidens frondosa)等之菊科雜草；合萌(Aeschynomene indica)等之豆科雜草；疣草(Murdannia keisak)等之鴨跖草科雜草；稻稗(Echinochloa
oryzicola)、野稗(Echinochloa crus-galli var.crus-galli)、台灣野稗(Echinochloa crus-galli var.formosensis)、細葉旱稗(Echinochloa crus-galli var.praticola)、長毛野稗(Echinochloa crus-galli var.caudata)、千金子(Leptochloa chinensis)、假稻(Leersia japonica)、雙穗雀稗(Paspalum distichum)、蓉草(Leersia oryzoides)等之禾本科雜草等。
又，就旱田、非農耕地而言，對下列列舉成為問題的各種雜草，於土壤處理、土壤混和處理及莖葉處理之任一者之處理方法皆具有除草效力。以下例示該雜草，但並未限定於此等例。
可列舉龍葵(Solanum nigrum)、曼陀羅花(Datura stramonium)等之茄科雜草；苘麻(Abutilon avicennae)、刺金午時花(Sida spinosa)等之錦葵科雜草；紫花牽牛(Ipomoea purpurea)等之旋花科雜草；凹頭莧(Amaranthuslividus)等之莧科雜草；蒼耳(Xanthium strumarium)、豬草(Ambrosia artemisiifolia)、粗毛牛膝菊(Galinsoga ciliata)、絲路薊(Cirsium arvense)、歐洲黃菀(Senecio vulgaris)、一年蓬(Stenactis annuus)等之菊科雜草；葶藶(Rorippa indica)、新疆白芥(Sinapis arvensis)、薺(Capsella bursa-pastoris)等之十字花科雜草；睫穗蓼(Persicaria longiseta)、卷莖蓼(Fallopia convolvulus)等之蓼科雜草；馬齒莧(Portulaca oleracea)等之馬齒莧科雜草；藜(Chenopodium album)、小葉灰藋(Chenopodium ficifolium)、地膚子(Kochia scoparia)等之藜科雜草；繁縷(Stellaria media)等之石竹科雜草；阿拉伯婆婆納
(Veronica persica)等之玄參科雜草；鴨跖草(Commelina communis)等之鴨跖草科雜草；寶蓋草(Lamium amplexicaule)、圓齒野芝麻(Lamium purpureum)等之唇形花科雜草；小錦草(Euphorbia supina)、斑地錦(Euphorbia maculata)等之大戟科雜草；豬殃殃(Galium spurium)、豬殃殃艾知諾斯特孟變種(Galium spurium var.echinospermon)、東南茜草(Rubia argyi)等之茜草科雜草；紫花地丁(Viola mandshurica)等之菫菜科雜草；田菁(Sesbania exaltata)、決明(Cassia obfusitolia)等之豆科雜草等之闊葉雜草；野生高粱(Sorghum bicolor)、洋野黍(Panicum dichotomiflorum)、詹森草(Sorghum halepense)、野稗(Echinochloa crus-galli var.crus-galli)、升馬唐(Digitaria ciliaris)、野燕麥(Avena fatua)、牛筋草(Eleusine indica)、狗尾草(Setaria viridis)、看麥娘(Alopecurus aequalis)、早熟禾(Poa annua)等之禾本科雜草；香附子(Cyperus rotundus)等之莎草科雜草等。
再者，可將割草地、休耕地、樹園地、牧草地、草地、線路端、空地、林業地、或農道、畦畔、其他非農耕地發生的廣範圍之雜草加以去除。
而且本發明之式(I)之化合物，於水稻之直播栽培或移植栽培等之任意的栽培方法亦未顯示對水稻有成為問題的藥害。
本發明之式(I)之化合物可施用於植物發芽前及發芽後任一者，再者，亦可於播種前與土壤混和。
本發明之式(I)之化合物之投藥量可因應化合物之種類、對象植物種類、適用時期、適用場所、所欲效果之性質等而於廣範圍變化，但就大致的標準而言，作為每1公畝之活性化合物，可例示約0.01~100g，較佳為約0.1~10g之範圍內。
本發明之式(I)之化合物亦可單獨使用，但通常係依據通常方法，於式(I)之化合物摻合調配輔助劑(formulation aid)等，其並未限定，但較佳例如製劑化為粉劑、乳劑、油劑、助溶劑、懸浮乳劑(suspoemulsion)、微粒劑、噴霧劑、DL粉劑、微粒劑F、細粒劑F、粒劑、水合劑、顆粒水合劑、可流動劑、珍寶(Jumbo)劑、錠劑、糊劑、油性懸浮液、水溶劑、顆粒水溶劑、液劑、微膠囊劑等之任意劑型來使用。
就製劑化可使用的調配輔助劑而言，並未限定，但例如可列舉固體載體、液體載體、結合劑、增黏劑、界面活性劑、防凍劑、防腐劑等。
就固體載體而言，並未限定，但例如可列舉滑石、膨潤土、蒙脫石、黏土、高嶺土、碳酸鈣、碳酸鈉、碳酸氫鈉、芒硝、沸石、澱粉、酸性白土、矽藻土、白碳、蛭石、消石灰、植物性粉末、氧化鋁、活性碳、糖類、玻璃中空體、矽砂、硫酸銨、尿素等。
就液體載體而言，並未限定，但例如可列舉烴類(例如，煤油、礦物油等)；芳香族烴類(例如，甲苯、二甲苯、二甲基萘、苯基二甲苯基乙烷等)；氯化烴類(例如，氯仿、四氯化碳等)；醚類(例如，二烷、四氫呋喃
等)；酮類(例如，丙酮、環己酮、異佛酮等)；酯類(例如，乙酸乙酯、乙二醇乙酸酯、馬來酸二丁酯等)；醇類(例如，甲醇、正-己醇、乙二醇等)；極性溶劑類(例如，N,N-二甲基甲醯胺、二甲亞碸、N-甲基吡咯啶酮等)；水等。
就結合劑及增黏劑而言，並未限定，但例如可列舉糊精、羧甲基纖維素之鈉鹽、聚羧酸系高分子化合物、聚乙烯吡咯啶酮、聚乙烯醇、木質素磺酸鈉、木質素磺酸鈣、聚丙烯酸鈉、阿拉伯樹膠、褐藻酸鈉、甘露糖醇、山梨糖醇、膨潤土系礦物質、聚丙烯酸及其衍生物、白碳、天然糖類衍生物(例如，三仙膠、瓜爾膠等)等。
就界面活性劑而言，並未限定，但例如可列舉脂肪酸鹽、苯甲酸鹽、烷基磺基琥珀酸鹽、二烷基磺基琥珀酸鹽、聚羧酸鹽、烷基硫酸酯鹽、烷基硫酸鹽、烷基芳基硫酸鹽、烷基二甘醇醚硫酸鹽、醇硫酸酯鹽、烷基磺酸鹽、烷基芳基磺酸鹽、芳基磺酸鹽、木質素磺酸鹽、烷基二苯基醚二磺酸鹽、聚苯乙烯磺酸鹽、烷基磷酸酯鹽、烷基芳基磷酸鹽、苯乙烯基芳基磷酸鹽、聚氧伸乙基烷基醚硫酸酯鹽、聚氧伸乙基烷基芳基醚硫酸鹽、聚氧伸乙基烷基芳基醚硫酸酯鹽、聚氧伸乙基烷基醚磷酸鹽、聚氧伸乙基烷基芳基磷酸酯鹽、萘磺酸福馬林縮合物之鹽等之陰離子系界面活性劑及山梨醇酐脂肪酸酯、甘油脂肪酸酯、脂肪酸聚甘油、脂肪酸醇聚乙二醇醚、乙炔二醇、乙炔醇、氧伸烷基嵌段聚合物、聚氧伸乙基烷基醚、聚氧伸乙基烷基芳基醚、聚氧伸乙基苯
乙烯基芳基醚、聚氧基乙二醇烷基醚、聚氧伸乙基脂肪酸酯、聚氧伸乙基山梨醇酐脂肪酸酯、聚氧伸乙基甘油脂肪酸酯、聚氧伸乙基硬化蓖麻油、聚氧伸丙基脂肪酸酯等之非離子系之界面活性劑。
就防凍劑而言，並未限定，但例如可列舉乙二醇、二乙二醇及丙二醇、甘油等。
就防腐劑而言，並未限定，但例如可列舉苯甲酸、苯甲酸鈉、對羥基苯甲酸甲酯、對羥基苯甲酸丁酯、異丙基甲基酚、氯化苄烷銨(benzalkonium chloride)、鹽酸氯己啶(chlorhexidine hydrochloride)、過氧化氫水、葡糖酸氯己啶、水楊酸、水楊酸鈉、吡啶硫酮鋅(zinc pyrithione)、山梨酸、山梨酸鉀、去氫乙酸、去氫乙酸鈉、苯氧基乙醇、5-氯-2-甲基-4-異噻唑啉-3-酮、2-甲基-4-異噻唑啉-3-酮等之異噻唑啉衍生物、2-溴-2-硝基丙烷-1,3-二醇、及水楊酸衍生物。
因應使用目的等，以上所述固體載體、液體載體、結合劑、增黏劑、界面活性劑、防凍劑及防腐劑可各自單獨或適當組合來使用。
本發明之式(I)之化合物相對於本發明之除草劑組成物全體之摻合比例，可因應必要加減而未特別限制，但通常為0.01~90質量%左右，例如，作成粉劑或者粒劑的情形，0.1~50質量%左右為較佳，更佳為0.5~10質量%左右；作成乳劑、水合劑或者顆粒水合劑等的情形係0.1~90質量%左右為較佳，更佳為0.5~50質量%左右。
此等之製劑藉由因應必要稀釋為適當濃度而噴灑或直接施用於植物莖葉、土壤、水田之水面等，可供給於各種用途。
藉由以下之實施例以說明本發明。
實施例1. 1-(3-氯-4,5,6,7-四氫吡唑并[1,5-a]吡啶-2-基)-5-(2-甲基丙-2-烯基胺基)吡唑-4-甲腈之製法(化合物1)
於5-胺基-1-(3-氯-4,5,6,7-四氫吡唑并[1,5-a]吡啶-2-基)吡唑-4-甲腈(19.7g)中添加乙腈(75ml)，於其中緩緩滴加乙酸氯(5.8g)，並進行加熱回流5小時。反應結束後，於反應液中添加水，將析出的固體以乙酸乙酯洗淨，獲得N-(1-(3-氯-4,5,6,7-四氫吡唑并[1,5-a]吡啶-2-基)-4-氰基吡唑-5-基)乙醯胺(12g)。
將獲得的N-(1-(3-氯-4,5,6,7-四氫吡唑并[1,5-a]吡啶-2-基)-4-氰基吡唑-5-基)乙醯胺(2.5g)溶於乙腈(8ml)，添加碳酸鉀(1.3g)並進行攪拌。於其中，添加3-氯-2-甲基-1-丙烯(0.8g)，並進行加熱回流8小時。反應結束後，於反應液中添加水並以乙酸乙酯提取。以硫酸鈉乾燥後，減壓濃縮溶劑，將獲得的固體以矽膠管柱層析法(己烷/乙酸乙酯=1：1)純化。將純化的化合物(1.3g)溶於乙醇(3ml)，添加氫氧化鈉(0.14g)及水(1ml)，於室溫進行反應1日。反應結束後，於反應液中添加水，將析出的固體以異丙基醚洗淨，獲得目的物(0.8g)。
實施例2. 1-(3-氯-4,5,6,7-四氫吡唑并[1,5-a]吡啶-2-基)-5-(2-氯丙-2-烯基胺基)吡唑-4-甲腈之製法(化合物2)
於冷卻至5℃的乙酸酐(33.7g)中緩緩滴加甲酸(18.4g)，於60℃進行攪拌2小時(反應液A)。另外，將5-胺基-1-(3-氯-4,5,6,7-四氫吡唑并[1,5-a]吡啶-2-基)吡唑-4-甲腈(26.3g)溶於乙腈(200ml)，並進行攪拌。於其中，緩緩滴加先前調製的反應液A，於室溫進行反應1日、於60℃進行反應4小時。之後，減壓濃縮溶劑，使用碳酸鉀水溶液中和，將析出的固體以水洗淨，乾燥後，獲得N-(1-(3-氯-4,5,6,7-四氫吡唑并[1,5-a]吡啶-2-基)-4-氰基吡唑-5-基)甲醯胺(28g)。
將獲得的N-(1-(3-氯-4,5,6,7-四氫吡唑并[1,5-a]吡啶-2-基)-4-氰基吡唑-5-基)甲醯胺(1.5g)溶於乙腈(5ml)，添加碳酸鉀(0.8g)，並進行攪拌。於其中，緩緩滴加2,3-二氯-1-丙烯(0.6g)，並於40℃進行反應3小時，反應結束後，於反應液中添加水並以乙酸乙酯提取。以硫酸鈉乾燥後，減壓濃縮溶劑，將粗生成物以矽膠管柱層析法(己烷/乙酸乙酯=1：1)純化，獲得N-(1-(3-氯-4,5,6,7-四氫吡唑并[1,5-a]吡啶-2-基)-4-氰基吡唑-5-基)-N-(2-氯丙-2-烯基)甲醯胺(1.73g)。
將獲得的N-(1-(3-氯-4,5,6,7-四氫吡唑并[1,5-a]吡啶-2-基)-4-氰基吡唑-5-基)-N-(2-氯丙-2-烯基)甲醯胺(1.73g)溶於乙醇(5ml)，添加10%鹽酸(6.9g)，並於室溫進行攪拌3小時。反應結束後，於反應液中添加水並濾取析出的固體，乾燥後，獲得目的物(4.1g)。
實施例3.(N-1-(3-氯-4,5,6,7-四氫吡唑并[1,5-a]吡啶-2-基)-4-氰基吡唑-5-基)-N-(2-氯丙-2-烯基)-2,2,2-三氟乙醯胺之製法(化合物3)
將1-(3-氯-4,5,6,7-四氫吡唑并[1,5-a]吡啶-2-基)-5-(2-氯丙-2-烯基)吡唑-4-甲腈(0.7g)溶於乙腈(5ml)，於其中緩緩滴加三氟乙酸酐(1.3g)。於40℃攪拌7日，於反應液中添加飽和碳酸氫鈉水溶液，並以乙酸乙酯提取。以硫酸鈉乾燥後，減壓餾除溶劑，將獲得的粗生成物以矽膠管柱層析法(己烷/乙酸乙酯=4：1)純化，獲得目的物(0.4g)。
起始材料的式(II)係依據WO93/10100及WO94/08999而合成。
以下表所列舉的實施例係與上述方法同樣地製造、或與上述方法同樣地獲得。
藉由將其混合並以鎚磨機進行微粉碎而獲得。
藉由將其混合，並將此混合物以鎚磨機進行微粉碎而獲得。
藉由將其混合，使用濕式粉碎機進行粉粹而獲得可流動劑。
藉由將其混合而獲得乳劑。
式(I)之化合物 5重量份
將其混合，添加水並混練後擠壓而造粒。之後藉由乾燥、整粒而獲得粒劑。
於1/10000公畝之盆中填充水田土壤，添加適量水及化學肥料並混練，將稗草、鴨舌草及螢藺之種子播種，維持水深3cm的注水狀態。
將依據製劑例所調製的表1所示之目的化合物(I)之水合劑以適量水加以稀釋，於稗草3.5葉期時移植2.0葉期之稻，使用吸量管以每公畝成為規定的藥量的方式作滴加處理。
然後於平均氣溫30℃之玻璃室中經30日管理後，調查彼等之除草效果。
除草效果之評價係與無處理區之狀態比較生長抑制率(%)，藥害之評價係與完全除草區的狀態比較生長抑制率(%)，而以下列11階段表示。
0(指數)：0%~小於10%(生長抑制率)、1：10%以上~小於20%、2：20%以上~小於30%、3：30%以上~小於40%、4：40%以上~小於50%、
5：50%以上~小於60%、6：60%以上~小於70%、7：70%以上~小於80%、8：80%以上~小於90%、9：90%以上~小於100%、10：100%
將其結果示於表2。
對照劑4.59(WO94/08999記載)
對照劑4.75(WO94/08999記載)
對照劑4.85、4.156(WO94/08999記載)
對照劑4.239(WO94/08999記載)
於1/6000公畝之盆中填充旱田土壤，將升馬唐、藜、反枝莧(Amaranthus retroflexus)之種子播種並覆土。
將依據製劑例所調製的表1所示的式(I)之化合物之水合劑以水稀釋成規定之藥量，於播種後雜草發生前以每公畝10公升的噴灑水量，於各土壤表層均一地噴霧處理。
然後於平均氣溫30℃之玻璃室管理30日後，調查彼等之除草效果。
除草效果之評價係與前述試驗例1同樣地進行。
其結果示於表3。
於1/6000公畝之盆中填充培養土，將升馬唐、藜、反枝莧之種子播種並覆土，於平均氣溫25℃之玻璃室中栽培。
於升馬唐生長成為1.0~2.0葉期的時期，將依據製劑例所調製的表1所示之目的化合物(I)之水合劑以水稀釋成規定之藥量，以每公畝15公升之噴灑水量於雜草上均一地噴霧處理。
然後於平均氣溫25℃之玻璃室中管理3週後，調查彼等之除草效果。
除草效果之評價係與前述試驗例1同樣地進行。
其結果示於表4。
依據本發明，因本發明之式(I)之化合物對不需要的植物具有優異的防治效果，故有用於作為有害植物防治劑。
Claims (8)
- 一種下式(I)所示的化合物，
- 如請求項1之化合物，其中R4、R5及R6可相同或相異，表示：(i)1個或以上之氫原子、(ii)1個或以上之鹵素原子、或者(iii)1個或以上之C1~C6烷基、1個或以上之C3~C6環烷基、1個或以上之C3~C6烷氧基-C1~C6烷基或1個或以上之苯基，此等依情形經1個或以上之鹵素原子取代，且a表示4。
- 如請求項1之化合物，其中R1表示氯原子，R2表示氰基，R4、R5及R6可相同或相異，表示：(i)1個或以上之氫原子、(ii)1個或以上之鹵素原子、或者(iii)1個或以上之C1~C6烷基，其依情形經1個或以上之鹵素原子取代，且b表示1。
- 一種除草劑組成物，其含有如請求項1、2或3中任一項之化合物之至少1者的除草有效量。
- 如請求項4之除草劑組成物，其進一步含有調配輔助 劑(formulation aid)。
- 一種防治不需要的植物之方法，其包含將如請求項1、2或3中任一項之化合物之至少1者的有效量施用於不需要的植物或不需要的植被的場所之步驟。
- 一種防治不需要的植物之方法，其包含將如請求項4或5之除草劑組成物施用於不需要的植物或不需要的植被的場所之步驟。
- 一種如請求項1、2或3中任一項之化合物之用途，其係用於製備防治不需要的植物用之除草劑組成物。
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| TW201632521A (zh) * | 2015-01-23 | 2016-09-16 | 協友股份有限公司 | 經取代之吡唑吡唑衍生物及其作爲除草劑的用途 |
| AR103473A1 (es) * | 2015-01-23 | 2017-05-10 | Kyoyu Agri Co Ltd | Derivado de pirazolilpirazol sustituido y su empleo como herbicida |
| TW201630908A (zh) | 2015-01-23 | 2016-09-01 | 協友股份有限公司 | 經取代之吡唑吡唑衍生物及其作爲除草劑的用途 |
| JP2016141627A (ja) * | 2015-01-30 | 2016-08-08 | 協友アグリ株式会社 | 除草剤組成物 |
| MX2018004622A (es) | 2015-10-14 | 2019-05-06 | First Quality Tissue Llc | Producto empaquetado y sistema y metodo para formar el mismo. |
| CN109400601B (zh) * | 2017-08-15 | 2021-09-14 | 海利尔药业集团股份有限公司 | 一种含吡唑基取代的吡唑衍生物及其制备和用途 |
| US11738927B2 (en) | 2018-06-21 | 2023-08-29 | First Quality Tissue, Llc | Bundled product and system and method for forming the same |
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| CN1087342A (zh) * | 1992-10-12 | 1994-06-01 | 先灵公司 | 新的取代的吡唑衍生物及其制备方法和作为除草剂的应用 |
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| DE3538731A1 (de) * | 1985-10-31 | 1987-05-07 | Bayer Ag | 1-aryl-4-nitro-pyrazole |
| IL103678A (en) * | 1991-11-13 | 1996-09-12 | Schering Ag | History of pyrazolylpyrazole, processes for their preparation and herbicidal preparations containing them |
| DE4435373A1 (de) * | 1994-09-22 | 1996-03-28 | Hoechst Schering Agrevo Gmbh | Substituierte Pyrazolyl-pyrazolderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Mittel mit herbizider Wirkung |
| DE19630555A1 (de) * | 1996-07-18 | 1998-01-22 | Hoechst Schering Agrevo Gmbh | Substituierte Pyrazolyl-pyrazolderivate |
| JP2005154420A (ja) | 2003-11-05 | 2005-06-16 | Toyo Kasei Kogyo Co Ltd | アルコキシ−５−（５−トリフルオロメチル−テトラゾール−１−イル）ベンズアルデヒドの製造方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1087342A (zh) * | 1992-10-12 | 1994-06-01 | 先灵公司 | 新的取代的吡唑衍生物及其制备方法和作为除草剂的应用 |
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| IL243614A0 (en) | 2016-02-29 |
| RU2016108486A3 (zh) | 2018-05-22 |
| EP3034503A4 (en) | 2017-03-15 |
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| JP2015036371A (ja) | 2015-02-23 |
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| CN105473589A (zh) | 2016-04-06 |
| RU2016108486A (ru) | 2017-09-15 |
| AU2014307435B2 (en) | 2018-03-22 |
| MX2016001144A (es) | 2016-04-29 |
| US9593122B2 (en) | 2017-03-14 |
| TW201536754A (zh) | 2015-10-01 |
| BR112016002384A2 (pt) | 2017-08-01 |
| UA116258C2 (uk) | 2018-02-26 |
| WO2015022924A1 (ja) | 2015-02-19 |
| CA2918240A1 (en) | 2015-02-19 |
| JP6128555B2 (ja) | 2017-05-17 |
| CN105473589B (zh) | 2018-05-08 |
| EP3034503A1 (en) | 2016-06-22 |
| RU2669394C2 (ru) | 2018-10-11 |
| US20160159807A1 (en) | 2016-06-09 |
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