TWI647216B - 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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- TWI647216B TWI647216B TW103127173A TW103127173A TWI647216B TW I647216 B TWI647216 B TW I647216B TW 103127173 A TW103127173 A TW 103127173A TW 103127173 A TW103127173 A TW 103127173A TW I647216 B TWI647216 B TW I647216B
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
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，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(或殘效性)，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、鹵素原子，R3表示氫原子、三氟乙醯基、五氟丙醯基、七氟丁烯基，R4~R9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)C2~C6烯基、(依情形經1個或以上之鹵素原子取代的)C2~C6炔基、(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烷氧基取代的)苯基，a表示3~5，且b表示0~2。
式(I)中，較佳係：R1表示氯原子、溴原子，R4~R9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~C4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)C2~C4烯基、(依情形經1個或以上之鹵素原子取代的)C2~C4炔基、(依情形經1個或以上之鹵素原子取代的)C1~C4烷氧基(C2~C4)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烷氧基取代的)苯基，a表示4。
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。
基本身或基之部分中所稱「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。
「烯基」意指直鏈狀或支鏈狀，且分子內具有1個或2個以上之雙鍵的不飽和烴基，且並未限定，但例如可列舉乙烯基、1-丙烯基、2-丙烯基、2-丁烯基、2-甲基-2-丙烯基、3-甲基-2-丁烯基、1,1-二甲基-2-丙烯基等作為具體例，係於各自指定的碳原子數的範圍內選擇。
「炔基」意指直鏈狀或支鏈狀，且分子內具有1個或2個以上之三鍵的不飽和烴基，且並未限定，但例如可列舉乙炔基、1-炔丙基、2-炔丙基、1-丁炔基、2-丁炔基、3-丁炔基、1,1-二甲基-2-炔丙基等作為具體例，係於各自指定的碳原子數的範圍內選擇。
「烷基」、「環烷基」、「烯基」、「炔基」、「烷氧基」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。
因應取代基之種類及鍵結樣式，式(I)之化合物可呈立體異構物存在。例如，若存有1個或以上之不對稱取代的碳原子時，此種立體異構物可為鏡像異構物及非鏡像異構物。立體異構物可由製造中獲得的混合物，藉由慣用之分離法，例如藉由層析分離步驟而獲得。立體異構物亦可藉由立體選擇反應之使用、光學活性起始材料及/或輔助劑之採用而製造。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立體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。本發明所提供的式(I)之化合物，例如可自式(II)所示的化合物，藉由以下之製法(A)、(B)、(C)之任一者而製造，或在製法(A)、(B)、(C)之任一者之後藉由製法(D)而製造：
一種式(I)之化合物之製造方法，其特徵為使前述式(II)之化合物與下式(III)所示的化合物於鹼存在下反應。
(式中X表示鹵素原子、甲苯磺酸酯、甲磺酸酯。)
一種式(I)之化合物之製造方法，其特徵為使前述式(II)之化合物與下式(IV)所示的化合物脫水縮合，作成希夫鹼(Schiff base)後，使其與還原劑反應。
一種式(I)之化合物之製造方法，其特徵為使前述式(II)之化合物與下式(V)所示的化合物反應而作成醯胺後，鹵化，接著使其與還原劑反應。
(式中Y表示羥基、烷氧基、鹵素原子。)
一種式(I)之化合物之製造方法，其特徵為於式(I)之化合物中R3不含有氫原子的情形，在製法(A)、(B)、(C)任一者之實施後，進行全氟醯胺化反應。
製法(A)、(B)、(C)任一者所使用的式(II)之化合物可依據WO93/10100及WO94/08999所記載的方法，由四氫-2H-吡喃-2-亞基乙腈或5-氯戊醯氯而合成。
於製法(A)作為另一種起始原料所使用的式(III)之化合物，其本身係已知之化合物，或者可與已知之化合物同樣地合成(例如，參照日本特開2011-173838、日本特表2000-504733、J.Org.Chem.1984，49，431-435、日本特表2011-506349)。
(II)之化合物與(III)之化合物之反應，其本身可參考周知之反應條件來實施(例如，參照WO94/08999)。
作為進行反應之際所使用的鹼，較佳可於至少1當量之適當鹼存在下，依情形，於適當溶劑之存在下處理。鹼可為無機鹼，例如：鹼金屬碳酸鹽或氫氧化物或金屬氫化物；或者有機鹼，例如：第三級胺或金屬烷氧化物。就適當無機鹼之例而言，可列舉碳酸鈉、氫氧化鈉或氫氧化鉀、氫化鈉，而且就適當有機鹼而言，可列舉三烷基胺，例如：三甲基胺及三乙基胺；吡啶或其他胺鹼，例如：4-N,N-二甲基胺基吡啶、N,N-二甲基苯胺、1,4-二氮雜雙環[2.2.2]辛烷、1,8-二氮雜雙環[5.4.0]十一碳-7-烯。此等通常係相對於式(II)之化合物，可於0.01~5倍莫耳之範圍內使用。
就該溶劑而言，例如，可列舉二乙基醚、四氫呋喃、二烷等之醚類；N,N-二甲基甲醯胺、二甲亞碸等之雙極性非質子溶劑類；苯、甲苯、二甲苯等之芳香族烴類；乙腈等之腈類，彼等之混合溶劑等。
又，因應必要可使用觸媒，就此種觸媒而言，並未限定，但例如可列舉氯化四甲基銨、溴化四甲基銨、氯化四乙基銨、溴化四乙基銨、氯化四丁基銨、溴化四丁基銨、氯化三甲基苯甲基銨、溴化三甲基苯甲基銨、氯化三乙基苯甲基銨、溴化三乙基苯甲基銨、氯化十六基三甲基銨、氯化三辛基甲基苯甲基銨、硫酸氫四丁基銨、四乙基銨、p-甲苯磺酸鹽、四丙基氫氧化銨、三甲基苯甲基氫氧化銨等之第4級銨鹽或5-冠-5、18-冠-6、苯并-15-冠-5、二苯并-18-冠-6、二環己烷并-18-冠-6等之冠醚類。
式(III)之化合物相對於式(II)之化合物之使用比例，並未特別限制，但一般而言，相對於式(II)之化合物1莫耳，期望在0.5~2莫耳，尤其1~1.2莫耳之範圍內來使用式(III)之化合物。
反應溫度可因應使用的起始原料之種類或觸媒之種類等而變換，但通常，為使用的溶劑之沸點以下的溫度，較佳可作成0~110℃之範圍內。
反應時間係依起始原料之種類或反應條件而異，但通常為0.5~72小時左右。
於製法(B)，作為另一種起始原料所使用的式(IV)之化合物係已有販售，或可藉由文獻(例如，日本特開2012-180338)及其引用的文獻所記載的周知方法而容易地製造。
為了使縮合(II)之化合物與(IV)之化合物之際所使用的希夫鹼生成的適當條件，係依存於起始物質
及所生成的化合物之性質，亦即溶解度、反應性、安定性等。此種條件亦有必要各別選擇，但例如可藉由文獻(日本特開平5-148240)及其引用的文獻所記載的周知縮合方法而容易地製造。
就使用的酸而言，只要為布忍斯特酸或路易士酸，可無特別限制地使用。例如，可適合使用硫酸、鹽酸、p-甲苯磺酸等。酸型之離子交換樹脂、酸性白土、異種多重酸(heteropoly acid)等之固體酸；及/或除水劑，例如硫酸鈉(或鎂)，或分子篩，例如molecular sieve。酸量並未特別限制，但宜為使用的羰基化合物、1級胺化合物及2級胺化合物之化學計量以下。又因應必要，為了促進反應，亦可藉由共沸蒸餾自反應混合物去除反應水。
就該溶劑而言，例如，可列舉二乙基醚、四氫呋喃、二烷等之醚類；N,N-二甲基甲醯胺、二甲亞碸等之雙極性非質子溶劑類；甲苯、二甲苯等之芳香族烴類；乙腈等之腈類；氯仿、四氯化碳、二氯甲烷等之鹵化烴類；彼等之混合溶劑等。
就希夫鹼還原時之溶劑而言，只要不顯著抑制反應者即可，可列舉二乙基醚、二烷、四氫呋喃(THF)等之醚類；甲醇、乙醇、丙醇、2-丙醇等之醇類等。就還原劑而言，並未特別限定，可使用一般的還原劑。具體而言可列舉硼烷THF錯合物、氫化硼鈉、氫化氰基硼鈉、氫化硼鋰、氫化鋰鋁等，此等中尤以氫化硼鈉為較佳。使用的還原劑之量，只要相對於希夫鹼為1當量以
上即可，但較佳為1.5~100當量之範圍，更佳為1.5~10當量之範圍。關於還原劑之添加方法並未特別限定，可不使還原劑溶解於溶劑，可一次添加，亦可逐次少量添加。還原劑之添加係依所欲，可於氮、氬等之惰性氣體環境下實施。反應溫度只要由-20℃~120℃之範圍選擇即可，較佳為0℃~室溫之範圍。反應時間依反應規模、反應溫度等而不一，但只要於1小時~24小時之範圍內依據通常方法來單離即可，因應必要可藉由結晶、蒸餾、管柱層析法等之方法來純化。
又，式(II)之化合物與式(IV)之化合物之反應，亦可使用能以一階段進行式(I)之化合物合成的還原胺化反應。可藉由文獻(例如，J.Org.Chem.1996，61，3849-3862、J.Am.Chem.Soc.1971，93，2897、Tetrahedron 2004，60，7899)及其引用的文獻所記載的周知方法而容易地製造。
作為於製法(C)之另一種起始原料所使用的式(V)之化合物係已有販售、或可以原本周知之方法而製造(例如，參照日本特表2003-509403)。
於製法(C)藉由(II)之化合物與(V)之化合物之反應所生成的醯胺化合物，可以下述條件而合成。羧酸與胺的縮合反應可藉由例如：Org.Synth.，I 82(1941)、日本特開昭61-15867而合成，醯氯與胺的反應可藉由例如：日本特開昭61-15867而合成，酯與胺的反應可藉由例如：J.Org.Chem.1963，28，2915而合成。
就生成的醯胺化合物之鹵化，接著與還原劑之方法而言，可以原本周知之方法而製造(例如，參照日本特開2001-72676)。
於製法(D)，全氟醯胺化反應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，參照日本特開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(Amaranthus
lividus)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)、决明(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 ha1epense)、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-(環丙基甲基胺基)吡唑-4-甲腈之製法(化合物1)
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(100g)溶於N,N-二甲基甲醯胺(400ml)，添加氫氧化鈉(16.8g)、溴化四丁基銨(觸媒量)並進行攪拌。於其中緩緩滴加氯甲基環丙烷(37.9g)，並於50℃進行反應2日。反應結束後，添加水，將析出的固體以乙酸乙酯洗淨，獲得目的物(75g)。
實施例2. 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-(環丙基甲基)-2,2,2-三氟乙醯胺之製法(化合物2)
將1-(3-氯-4,5,6,7-四氫吡唑并[1,5-a]吡啶-2-基)-5-(環丙基甲基胺基)吡唑-4-甲腈(3.5g)溶於乙腈(10ml)，攪拌後，於其中緩緩滴加三氟乙酸酐(11.6g)。於50℃攪拌1日，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(3.5g)。
實施例3. 1-(3-氯-4,5,6,7-四氫吡唑并[1,5-a]吡啶-2-基)-5-(環丙基甲基胺基)吡唑-4-甲腈之製法(化合物1其他方法)
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(5.3g)溶於乙腈(20ml)，攪拌後，於其中緩緩滴加環丙烷羧酸氯(2.5g)，進行3小時回流。反應結束後，將反應液降至室溫，添加水，將析出的固體依序以己烷、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)環丙烷甲醯胺(3.8g)。
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)環丙烷甲醯胺(1.6g)溶於甲苯(10ml)，添加五氯化磷(1.25g)，並進行2小時回流。追加五氯化磷(0.13g)後，再進行1小時回流，於室溫進行攪拌1日。將反應液置入冰水，以氯仿提取，以0.1eq.
氫氧化鈉水溶液洗淨後，以硫酸鈉乾燥，並減壓濃縮。將獲得的粗生成物以己烷洗淨後，於其中添加乙醇(10ml)及氫化硼鈉(190mg)，並於室溫進行反應1日。反應結束後，添加水並以乙酸乙酯提取，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=2：1)純化，獲得目的物(1.2g)。
實施例4. 1-(3-氯-4,5,6,7-四氫吡唑并[1,5-a]吡啶-2-基)-5-(1-環丙基乙基胺基)吡唑-4-甲腈之製法(化合物9)
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(20g)、p-甲苯磺酸一水合物(4.34g)溶於甲苯(100ml)，攪拌後，添加環丙基甲基酮(31.9g)並進行回流2日。反應所生成的水使用分子篩4A去除。反應結束後，於50℃以矽藻土過濾，及以乙酸乙酯洗淨後，將濾液以任意比例加以濃縮後，以矽膠管柱層析法(己烷/乙酸乙酯=1：2)純化。於獲得的黏稠化合物中添加乙醇(200ml)、氫化硼鈉(5.8g)，並於室溫進行反應1日。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=1：1)純化而獲得目的物(6.2g)。
實施例5. 1-(3-氯-4,5,6,7-四氫吡唑并[1,5-a]吡啶-2-基)-5-(二環丙基甲基胺基)吡唑-4-甲腈之製法(化合物10)
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(10g)、p-甲苯磺酸一水合物(2.2g)溶於甲苯(50ml)，攪拌後，添加環丙基甲基酮(8.8g)，並進行5.5小時回流。反應所生成的水使用分子篩4A去除。反應結束後，於50℃進行矽藻土過濾及以乙酸乙酯洗淨後，減壓餾除溶劑。於獲得的化合物中添加乙醇(40ml)、氫化硼鈉(1.5g)，並於室溫進行反應1日。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。將獲得的粗生成物以矽膠管柱層析法(己烷/乙酸乙酯=1：1)純化，而獲得目的物(2.1g)。
實施例6. 1-(3-氯-4,5,6,7-四氫吡唑并[1,5-4]吡啶-2-基)-5-((1-甲基環丙基)甲基胺基)吡唑-4-甲腈之製法(化合物4)
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(64.5g)溶於N,N-二甲基甲醯胺(250ml)，添加氫氧化鈉(24.5g)、溴化四丁基銨(1.8g)並進行攪拌。於其中緩緩滴加1-(溴甲基)-1-甲基環丙烷(44.0g)，並於70℃進行反應2日。反應結束後，添加水並以乙酸乙酯提取，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=1：1)純化，獲得目的物(50g)。
實施例7. 呈示上述反應所使用的1-(溴甲基)-1-甲基環丙烷之製造例。
將1-甲基環丙烷甲酸(100g)溶於四氫呋喃(1.311)，攪拌後，將氫化硼鈉(34g)分數次逐次少量添加。於其中
緩緩滴加三氟化硼二乙基醚錯合物(170g)，並於室溫進行3日攪拌。3日後將反應液注入冰水中，過濾分離析出的固體後，減壓餾除四氫呋喃並以二氯甲烷進行提取，以硫酸鈉進行乾燥。乾燥後，減壓餾除溶劑，並獲得(1-甲基環丙基)甲醇(70g)。
將獲得的(1-甲基環丙基)甲醇(70g)溶於二氯甲烷(1.511)，並進行攪拌。於其中添加四溴化碳(371g)，將反應液以冰浴冷卻，緩緩滴加溶於二氯甲烷(500ml)的三苯基膦(294g)，並於室溫進行反應2日。反應結束後餾除溶劑，添加N,N-二甲基甲醯胺(300ml)並進行減壓蒸餾，獲得目的物(72g)。
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。
式(I)之化合物 10重量份
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。
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4.84(WO94/08999記載)
對照劑4.129(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 (9)
- 一種下式(I)所示的化合物或其立體異構物，
- 如請求項1之化合物或其立體異構物，其中R1表示氯原子、或溴原子， R4~R9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~C4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C2~C4烯基、依情形經1個或以上之鹵素原子取代的C2~C4炔基、依情形經1個或以上之鹵素原子取代的C1~C4烷氧基-C2~C4烷基、或者依情形經下列所取代的苯基：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，且a表示4。
- 如請求項1或2之化合物或其立體異構物，其中該立體異構物係選自鏡像異構物及非鏡像異構物之至少1種。
- 一種如請求項1之化合物或其立體異構物之製造方法，其含有將下式(Ⅱ)所示的化合物作為起始原料而使用的步驟，
- 一種除草劑組成物，其含有如請求項1至3中任一項 之化合物或其立體異構物之至少1種的除草有效量。
- 如請求項5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至3中任一項之化合物或其立體異構物之至少1種的有效量或如請求項5或6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。
- 一種如請求項1至3中任一項之化合物或其立體異構物或如請求項5或6之除草劑組成物之用途，其係用於防治不需要的植物。
- 如請求項8之用途，其中如請求項1至3中任一項之化合物或其立體異構物係用於防治有用植物之農作物中不需要的植物。
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