CN113614079A - 杂环酰胺化合物的结晶及其制造方法 - Google Patents
杂环酰胺化合物的结晶及其制造方法 Download PDFInfo
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- CN113614079A CN113614079A CN202080020669.0A CN202080020669A CN113614079A CN 113614079 A CN113614079 A CN 113614079A CN 202080020669 A CN202080020669 A CN 202080020669A CN 113614079 A CN113614079 A CN 113614079A
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Abstract
本发明的课题是杂环酰胺化合物的结晶及其制造方法。解决手段是阐明了式(1)所示的、作为具有作为除草剂有用的活性的化合物的杂环酰胺化合物具有新的结晶。
Description
技术领域
本发明涉及3-[(异丙基磺酰基)甲基]-N-(5-甲基-1,3,4-二唑-2-基)-5-(三氟甲基)-[1,2,4]三唑并[4,3-a]吡啶-8-甲酰胺[以下,简称为化合物(1)]的新的结晶和调制该结晶的方法。
背景技术
化学化合物的固体状态能够为非晶性(即,原子的距离没有长程有序)或结晶性(即,原子以有序的反射图案排列)。此外迄今不能够预测化学化合物的固体状态能够存在的晶形的熔点或溶解度等物理化学特性。此外迄今难以预测化合物的固体状态能以非晶性或结晶性存在。
另一方面,本发明所包含的化合物(1)作为作为除草剂有用的杂环酰胺化合物之一是已知的(例如,参照专利文献1~专利文献4)。
现有技术文献
专利文献
专利文献1:国际公开第2014/192936号
专利文献2:日本特开2016-153397号公报
专利文献3:日本特开2017-025054号公报
专利文献4:日本特开2019-019118号公报
发明内容
发明所要解决的课题
一般而言迄今不能制造化合物的特定的结晶、此外不能预测所得的结晶的熔点/水溶解度等物理特性。
本发明的目的是提供化合物(1)的新的结晶及其制造法。
用于解决课题的手段
本发明人等进行了深入研究,结果发现了化合物(1)具有新的结晶。即,本发明涉及下述〔1〕~〔4〕所记载的化合物(1)的结晶(以下,简称为本发明结晶)、下述〔5〕~〔8〕所记载的包含本发明结晶的组合物(以下,简称为本发明组合物)、下述〔9〕~〔10〕所记载的使用了本发明结晶的杂草的防除方法。
〔1〕
式(1)所示的杂环酰胺化合物的结晶,在采用Cu-Kα射线的粉末X射线衍射中,在衍射角2θ=7.29°±0.2、12.62°±0.2、14.13°±0.2、17.51°±0.2、18.64°±0.2、19.03°±0.2、20.56°±0.2、20.89°±0.2、21.76°±0.2、23.37°±0.2、25.41°±0.2、27.70°±0.2和30.34°±0.2具有峰。
〔2〕
式(1)所示的杂环酰胺化合物的结晶,在采用Cu-Kα射线的粉末X射线衍射中,在衍射角2θ=7.29°±0.1、12.62°±0.1、14.13°±0.1、17.51°±0.1、18.64°±0.1、19.03°±0.1、20.56°±0.1、20.89°±0.1、21.76°±0.1、23.37°±0.1、25.41°±0.1、27.70°±0.1、30.34°±0.1具有峰。
〔3〕
式(1)所示的杂环酰胺化合物的结晶,在采用Cu-Kα射线的粉末X射线衍射中,在衍射角2θ=7.29°、12.62°、14.13°、17.51°、18.64°、19.03°、20.56°、20.89°、21.76°、23.37°、25.41°、27.70°、30.34°具有峰。
〔4〕
根据上述〔1〕~〔3〕中任一项所述的杂环酰胺化合物的结晶,在采用Cu-Kα射线的粉末X射线衍射中,显示与本申请附图的图1实质上相同的衍射曲线。
〔5〕
一种农药组合物,其含有上述〔1〕~〔3〕中任一项所述的结晶。
〔6〕
一种除草剂组合物,其含有上述〔1〕~〔3〕中任一项所述的结晶。
〔7〕
一种悬浮状组合物,其含有上述〔1〕~〔3〕中任一项所述的结晶和分散介质。
〔8〕
一种水性悬浮状组合物,其含有上述〔1〕~〔3〕中任一项所述的结晶、表面活性剂和作为分散介质的水。
〔9〕
一种杂草的防除方法,其包含应用对防除杂草有效的量的上述〔5〕~〔8〕中任一项所述的组合物的工序。
〔10〕
根据上述〔9〕所述的杂草的防除方法,其包含将对防除杂草有效的量的上述〔5〕~〔8〕中任一项所述的组合物进行茎叶散布的工序。
发明的效果
根据本发明,可以再现性好地获得化合物(1)的结晶。
附图说明
图1为本发明结晶的粉末X射线衍射图
图2为本发明结晶的差示扫描量热测定图
图3为参考例1中的、化合物(1)的非晶体的粉末X射线衍射图
图4为参考例1中的、化合物(1)的非晶体的差示扫描量热测定图
具体实施方式
以下显示本发明结晶的粉末X射线衍射峰。
2θ=7.29°、12.62°、14.13°、17.51°、18.64°、19.03°、20.56°、20.89°、21.76°、23.37°、25.41°、27.70°、30.34°。
此外,作为粉末X射线衍射峰的误差,通常为±0.2,根据情况而能够取±0.1,因此考虑了误差的本发明结晶的峰值通常为2θ=7.29°±0.2、12.62°±0.2、14.13°±0.2、17.51°±0.2、18.64°±0.2、19.03°±0.2、20.56°±0.2、20.89°±0.2、21.76°±0.2、23.37°±0.2、25.41°±0.2、27.70°±0.2、30.34°±0.2,根据情况而为2θ=7.29°±0.1、12.62°±0.1、14.13°±0.1、17.51°±0.1、18.64°±0.1、19.03°±0.1、20.56°±0.1、20.89°±0.1、21.76°±0.1、23.37°±0.1、25.41°±0.1、27.70°±0.1、30.34°±0.1。
上述所示的粉末X射线衍射峰的测定条件如下所述。
〔粉末X射线衍射〕
装置:X’PERT-PRO MPD(スペクトリス株式会社制)
测定法:透射法
X射线:Cu-Kα
电压:45kV
电流:40mA
取样间隔:0.0070deg
数据范围:2θ=5~40deg
本发明结晶的熔点为216~218℃,在差示扫描量热测定中未观察到与熔点相比低温区域的吸热峰。
上述所示的熔点测定中的差示扫描量热测定的条件如下所述。
[差示扫描量热测定条件]
装置:DSC-60(株式会社岛津制作所制)
升温:20℃-(10℃/min)-450℃
气氛:氮气
对照:Al2O3
容器:SUS制
取样:1秒
接下来,以下说明本发明结晶的制造方法。
通过将化合物(1)加温而溶解于溶剂并将所得的溶液缓慢冷却使其结晶化的方法、或从所得的溶液将溶剂蒸馏除去使其结晶化的方法来获得本发明结晶。作为所使用的溶剂,只要是相对于化合物(1)为非活性的溶剂即可,可以使用例如,二乙基醚、甲基-叔丁基醚、四氢呋喃、二甲氧基甲烷、二乙氧基甲烷、1,2-二甲氧基乙烷、乙二醇二甲基醚、乙二醇二乙基醚、乙二醇二丁基醚、二甘醇二甲基醚、二甘醇二乙基醚、二甘醇二丁基醚、三甘醇二甲基醚、1,4-二烷等醚系溶剂、甲醇、乙醇、1-丙醇、2-丙醇、1-丁醇、2-丁醇、异丁醇、2-甲基-2-丙醇、甲基溶纤剂、乙基溶纤剂、异丙基溶纤剂、二甘醇单甲基醚、二甘醇单乙基醚、二甘醇单丁基醚、环己醇、苄基醇等醇系溶剂、正戊烷、正己烷、环己烷、甲基环己烷、正庚烷、正辛烷、正癸烷等脂肪族烃系溶剂、苯、甲苯、二甲苯、氯苯、邻二氯苯、间二氯苯、对二氯苯、硝基苯、四氢萘等芳香族烃系溶剂、乙腈、丙腈等腈系溶剂、乙酸甲酯、乙酸乙酯、乙酸丁酯、丙酸乙酯等酯系溶剂、二氯甲烷、氯仿、四氯化碳、1,2-二氯乙烷、1,1,2-三氯乙烷等卤代烃系溶剂、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基吡咯烷酮等酰胺系溶剂、1,3-二甲基咪唑烷酮、N,N,N’,N’-四甲基脲等脲系溶剂、二甲亚砜、环丁砜等含硫系极性溶剂、吡啶、2-皮考啉、3-皮考啉、4-皮考啉、5-乙基-2-皮考啉等吡啶系溶剂、丙酮、甲基乙基酮、二乙基酮、甲基异丁基酮等酮系溶剂、水等,这些溶剂可以单独使用或混合使用2种以上。这些溶剂中,优选为醚系溶剂、芳香族烃系溶剂、酯系溶剂、卤代烃系溶剂、酰胺系溶剂,进一步更优选为1,4-二烷、甲苯、乙酸乙酯、1,2-二氯乙烷、N,N-二甲基甲酰胺。
所使用的溶剂的使用量相对于化合物(1)的1重量份,通常为0.5~50重量份,优选为1~30重量份。
使化合物(1)溶解于溶剂的温度通常为30~150℃,优选为30~100℃。
进行冷却的速度通常为0.1~80℃/小时,优选为1~60℃/小时,随时可以在上述范围内变更为任意的冷却速度。
取出析出了的结晶时的溶液的温度通常为-30~50℃,优选为-20~30℃。
晶析所需要的时间通常为0.1~100小时,优选为1~50小时。
此外,在将溶剂蒸馏除去的情况下,可以通过在大气压下加热直到溶剂的沸点以上来蒸馏除去。此外通过调节容器内的减压度,可以在直到减压下的溶剂沸点为止的任意温度下将溶剂蒸馏除去。
本发明结晶与化合物(1)的非晶体相比,例如化学稳定性、光稳定性、吸湿性、悬浮性、过滤性等那样的特性、残留溶剂的除去性等制造上的特性优异。
接下来,对本发明组合物详细地说明。
在本发明组合物为水性悬浮状农药组合物的情况下,作为可以使用的分散介质,可以使用水或本发明结晶难以溶解的有机液体。作为该有机液体,可举出例如乙二醇、二甘醇、丙二醇、双丙甘醇和异丙醇等醇类、丁基溶纤剂等醚、环己酮等酮、γ-丁内酯等酯、N-甲基吡咯烷酮和N-辛基吡咯烷酮等酸酰胺、二甲苯、烷基苯、苯基二甲苯基乙烷和烷基萘等芳香族烃、机械油、正链烷烃、异链烷烃和环烷烃等脂肪族烃、煤油等芳香族烃与脂肪族烃的混合物、豆油、亚麻籽油、菜籽油、椰油、棉籽油和蓖麻油等油脂。
本发明结晶的含量相对于本发明组合物100重量份,通常为0.1~50重量份,更优选为1~30重量份。
此外,除了本发明结晶以外,还可以进一步含有1种以上公知的农药,例如除草剂、安全剂、杀虫剂、杀螨剂、杀线虫剂、抗病毒剂、植物生长调节剂、杀菌剂、增效剂、引诱剂和驱避剂等,在该情况下可以显示更优异的防除效果。作为公知的农药,特别优选的是除草剂、安全剂、杀菌剂、杀线虫剂和杀虫剂。具体而言,如果例示其通用名则如下所述,但不一定仅限定于此。
除草剂:4-CPA、4-CPA的盐(4-CPA-salts)、4-CPB、4-CPP、2,4-D(2,4-PA)、2,4-D的盐(2,4-D-salts)、2,4-D的酯(2,4-D-esters)、3,4-DA、2,4-DB、2,4-DB的盐(2,4-DB-salts)、2,4-DB的酯(2,4-DB-esters)、3,4-DB、2,4-DEB、2,4-DEP、3,4-DP、2,4,5-T、2,4,5-T的盐(2,4,5-T-salts)、2,4,5-T的酯(2,4,5-T-esters)、2,4,5-TB、2,3,6-TBA(TCBA)、2,3,6-TBA的盐(2,3,6-TBA-salts)、乙草胺(acetochlor)、三氟羧草醚(acifluorfen)、三氟羧草醚甲酯(acifluorfen-methyl)、三氟羧草醚钠盐(acifluorfen-sodium)、苯草醚(aclonifen)、丙烯醛(acrolein)、甲草胺(alachlor)、二丙烯草胺(allidochlor、CDAA)、禾草灭(alloxydim)、禾草灭钠盐(alloxydim-sodium)、烯丙醇(allylalchol)、五氯戊酮酸(alorac)、特津酮(ametridione)、莠灭净(ametryn)、特草嗪酮(amibuzin)、氨唑草酮(amicarbazone)、先甲草胺(amidochlor)、酰嘧磺隆(amidosulfuron)、氯丙嘧啶酸(aminocyclopyrachlor)、氯丙嘧啶酸甲酯(aminocyclopyrachlor-methyl)、氯丙嘧啶酸钾盐(aminocyclopyrachlor-potassium)、氯氨吡啶酸(aminopyralid)、氯氨吡啶酸的盐(aminopyralid-salts)、胺草磷(amiprophos)、甲基胺草磷(amiprophos-methyl)、杀草强(amitrole、aminotriazole、ATA)、氨基磺酸铵(ammonium sulfamate、AMS)、莎稗磷(anilofos)、疏草隆(anisuron)、磺草灵(asulam)、磺草灵的盐(asulam-salts)、阿特拉通(atraton)、莠去津(atrazine)、唑啶草酮(azafenidin)、四唑嘧磺隆(azimsulfuron)、叠氮津(aziprotryne、azyprotryn)、燕麦灵(barban、CBN)、1BCPC、氟丁酰草胺(beflubutamid)、精氟丁酰草胺(beflubutamid-M)、草除灵酸(benazolin)、草除灵(benazolin-ethyl)、草除灵酸的盐(benazolin-salts)、苯唑磺隆(bencarbazone)、乙丁氟灵(benfluralin、benefin)、呋草黄(benfuresate)、苄嘧磺隆酸(bensulfuron)、苄嘧磺隆(bensulfuron-methyl)、地散磷(bensulide、SAP)、灭草松(bentazon、bentazone)、灭草松钠(bentazone-sodium)、苯草灭(bentranil)、苯草多克死(benzadox)、苯草多克死铵(benzadox-ammonium)、双苯嘧草酮(benzfendizone)、苄草胺(benzipram)、双环磺草酮(benzobicyclon)、吡草酮(benzofenap)、氟草黄(benzofluor)、新燕灵酸(benzoylprop)、新燕灵(benzoylprop-ethyl)、苯噻隆(benzthiazuron)、氟吡草酮(bicyclopyrone)、甲羧除草醚(bifenox)、双丙氨膦酸(bilanafos、bialaphos)、双丙氨膦(bilanafos-sodium)、乐杀螨(binapacryl)、双草醚酸(bispyribac)、双草醚(bispyribac-sodium)、ビクスロゾン(bixlozone)十水四硼酸钠(borax)、除草定(bromacil)、除草定的盐(bromacil-salts)、糠草腈(bromobonil)、溴丁酰草胺(bromobutide)、溴酚肟(bromofenoxim)、ブロモピラゾン(bromopyrazon)、溴苯腈(bromoxynil)、溴苯腈钾盐(bromoxynil-potassium)、溴苯腈的酯(bromoxynil-esters)、丁草胺(butachlor)、氟丙嘧草酯(butafenacil)、抑草磷(butamifos)、丁烯草胺(butenachlor)、双丁乐灵(butralin、butraline)、丁噻咪草酮(buthidazole)、丁噻隆(buthiuron)、丁苯草酮(butroxydim)、炔草隆(buturon)、丁草敌(butylate)、唑草胺(cafenstrole)、氰氨化钙(calcium cyanamide)、克草胺酯(cambendichlor)、氯酸钙(calcium chlorate)、除草隆(carbasulam)、双酰草胺(carbetamide)、特噁唑威(carboxazole)、唑草酸(carfentrazone)、唑草酯(carfentrazone-ethyl)、CDEA、CEPC、甲氧除草醚(chlomethoxyfen、chlomethoxynil)、草灭喂(chloramben)、草灭喂的盐(chloramben-salts)、草灭畏甲酯(chloramben-methyl)、草灭畏甲胺盐(chloramben-methylammonium)、丁酰草胺(chloranocryl、dicryl)、ク炔禾灵酸(chlorazifop)、炔禾灵(chlorazifop-propargyl)、可乐津(chlorazine)、氯溴隆(chlorbromuron)、氯炔灵(chlorbufam、BIPC)、氯特龙(chloreturon)、伐草克(chlorfenac、fenac)、伐草克的盐(chlorfenac-salts)、燕麦酸(chlorfenprop)、燕麦酯(chlorfenprop-methyl)、氟脒杀(chlorflurazole)、整形酸(chlorflurenol)、整形醇(chlorflurenol-methyl)、氯草敏(chloridazon、PAC、pyrazon)、氯嘧磺隆酸(chlorimuron)、氯嘧磺隆(chlorimuron-ethyl)、氯乙灵(chlornidine)、草枯醚(chlornitrofen、CNP)、氯乙酸(chloroacetic acid、monochloroacetic acid)、氯乙酸钠(sodium chloroacetate、SMA)、绿麦隆(chlorotoluron)、枯草隆(chloroxuron)、羟敌草腈(chloroxynil)、草败死(chlorprocarb)、氯酞亚胺(chlorphtalim)、氯苯胺灵(chlorpropham、IPC)、氯磺隆(chlorsulfuron)、氯酞酸(chlorthal、TCTP)、氯酞酸的酯(chlorthal-esters)、氯硫酰草胺(chlorthiamid、DCBN)、吲哚酮草酯(cinidon-ethyl)、环庚草醚(cinmethylin)、醚磺隆(cinosulfuron)、咯草隆(cisanilide)、氯酰草膦(clacyfos)、烯草酮(clethodim)、碘氯啶酯(cliodinate)、炔草酸(clodinafop)、炔草酯(clodinafop-propargyl)、草丙酸(clofop)、草丙酯(clofop-isobutyl)、异草酮(clomazone)、氯甲酰草胺(clomeprop)、调果酸(cloprop)、环己烯草酮(cloproxydim)、二氯吡啶酸(clopyralid)、二氯吡啶酸甲酯(clopyralid-methyl)、二氯吡啶酸的盐(clopyralid-salts)、氯酯磺草胺酸(cloransulam)、氯酯磺草胺(cloransulam-methyl)、硫酸铜(2价)(copper sulfate)、CPMF、CPPC、醚草敏(credazine)、甲酚(cresol)、苄草隆(cumyluron)、氰草净(cyanatryn)、氨腈(cyanamide)、氰草津(cyanazine)、环草敌(cycloate)、シクロピラニル(cyclopyranil)、シクロピリモレート(cyclopyrimorate)、环丙嘧磺隆(cyclosulfamuron)、噻草酮(cycloxydim)、环莠隆(cycluron、COMU)、氰氟草酯酸(cyhalofop)、氰氟草酯(cyhalofop-butyl)、牧草快(cyperquat)、牧草快氯化物(cyperquat-chloride)、环丙津(cyprazine)、三环噻草胺(cyprazole)、环酰草胺(cypromid)、杀草隆(daimuron、dymron)、茅草枯(dalapon)、茅草枯的盐(dalapon-salts)、棉隆(dazomet)、棉隆钠盐(dazomet-sodium)、异丁草胺(delachlor)、甜菜安(desmedipham)、敌草净(desmetryn)、燕麦敌(di-allate)、麦草畏(dicamba、MDBA)、麦草畏的盐(dicamba-salts)、麦草畏的酯(dicamba-esters)、敌草腈(dichlobenil、DBN)、ジクロラウレア(dichloraurea、DCU)、苄胺灵(dichlormate)、邻二氯苯(o-dichlorobenzene、DCB)、2,4-滴丙酸(dichlorprop)、2,4-滴丙酸的盐(dichlorprop-salts)、2,4-滴丙酸的酯(dichlorprop-esters)、精2,4-滴丙酸(dichlorprop-P)、精2,4-滴丙酸的盐(dichlorprop-P-salts)、精2,4-滴丙酸的酯(dichlorprop-P-esters)、禾草灵酸(diclofop)、禾草灵(diclofop-methyl)、精禾草灵酸(diclofop-P)、精禾草灵(diclofop-P-methyl)、双氯磺草胺(diclosulam)、二乙除草双(diethamquat)、二氯化二乙除草双(diethamquat dichloride)、乙酰甲草胺酸(diethatyl)、乙酰甲草胺(diethatyl-ethyl)、戊味禾草灵(difenopenten)、戊味禾草灵乙酯(difenopenten-ethyl)、枯莠隆(difenoxuron)、野燕枯(difenzoquat)、野燕枯甲基硫酸酯(difenzoquat metilsulfate)、吡氟酰草胺(diflufenican)、氟吡草腙(diflufenzopyr)、氟吡草腙钠盐(diflufenzopyr-sodium)、唑隆(dimefuron)、哌草丹(dimepiperate)、二甲草胺(dimethachlor)、异戊乙净(dimethametryn)、二甲吩草胺(dimethenamid)、精二甲吩草胺(dimethenamid-p)、敌灭生(dimexano)、草哒酮(dimidazon)、二甲基二硫醚(dimethyl disulfide)、氨氟灵(dinitramine)、地乐特(dinofenate)、丙硝酚(dinoprop)、戊硝酚(dinosam)、地乐酚(dinoseb、DNBP)、地乐酚的盐(dinoseb-salts)、地乐酚的酯(dinoseb-esters)、特乐酚(dinoterb)、特乐酚的盐(dinoterb-salts)、特乐酚的酯(dinoterb-esters)、双苯酰草胺(diphenamid)、地乐灵(dipropalin)、异丙净(dipropetryn)、敌草快(diquqt)、敌草快二溴化物(diquqt dibromide)、赛松(disul、2,4-PS)、赛松钠(disul-sodium)、氟硫草定(dithiopyr)、敌草隆(diuron、DCMU)、DMPA、DNOC、DNOC的盐(DNOC-salts)、EBEP、甘草津(eglinazine)、甘草津乙酯(eglinazine-ethyl)、茵多酸(endothal)、茵多酸的盐(endothal-salts)、三唑磺(epronaz)、EPTC、抑草蓬(erbon)、戊草丹(esprocarb)、克草胺(ethachlor)、乙丁烯氟灵(ethalfluralin)、胺苯磺隆(ethametsulfuron)、胺苯磺隆酸(ethametsulfuron-methyl)、杀草胺(ethaprochlor)、磺噻隆(ethidimuron)、硫草敌(ethiolate)、乙嗪草酮(ethiozin)、乙氧呋草黄(ethofumesate)、氟乳醚酸(ethoxyfen)、氯氟草醚乙酯(ethoxyfen-ethyl)、乙氧磺隆(ethoxysulfuron)、硝草酚(etinofen)、乙胺草醚(etnipromid)、乙氧苯草胺(etobenzanid)、EXD、酰苯磺威(fenasulam)、2,4,5-涕丙酸(fenoprop、2,4,5-TP、silvex)、2,4,5-涕丙酸的盐(fenoprop-salts)、2,4,5-涕丙酸的酯(fenoprop-esters)、唑禾草灵酸(fenoxaprop)、唑禾草灵(fenoxaprop-ethyl)、精唑禾草灵酸(fenoxaprop-p)、精唑禾草灵(fenoxaprop-p-ethyl)、苯磺唑草(fenoxasulfone)、酚醌草酮(fenquinotrione)、三氯苯氧乙醇(fenteracol)、噻唑禾草灵酸(fenthiaprop)、噻唑禾草灵(fenthiaprop-ethyl)、四唑酰草胺(fentrazamide)、硫酸铁(2价)(ferrous sulfate)、非草隆(fenuron)、非草隆TCA(fenuron-TCA)、麦草氟(flamprop)、麦草氟的酯(flamprop-esters)、精麦草氟(flamprop-M)、精麦草氟的酯(flamprop-M-esters)、啶嘧磺隆(flazasulfuron)、双氟磺草胺(florasulam)、氯氟吡啶酸(florpyrauxifen)、氯氟吡啶酯(florpyrauxifen-benzyl)、吡氟禾草灵(fluazifop)、吡氟禾草灵的酯(fluazifop-esters)、精吡氟禾草灵(fluazifop-P)、精吡氟禾草灵的酯(fluazifop-p-esters)、异丙吡草酯(fluazolate)、氟唑磺隆酸(flucarbazone)、氟唑磺隆(flucarbazone-sodium)、氟吡磺隆(flucetosulfuron)、氯乙氟灵(fluchloralin)、氟噻草胺(flufenacet)、吡氟酰草胺(flufenican)、氟哒嗪草酸(flufenpyr)、氟哒嗪草酯(flufenpyr-ethyl)、唑嘧磺草胺(flumetsulam)、氟默嗪(flumezin)、氟胺草酸(flumiclorac)、氟胺草酯(flumiclorac-pentyl)、丙炔氟草胺(flumioxazin)、炔草胺(flumipropyn)、氟草隆(fluometuron)、三氟硝草醚(fluorodifen)、乙羧氟草醚酸(fluoroglycofen)、乙羧氟草醚(fluoroglycofen-ethyl)、唑啶草(fluoromidine)、氟除草醚(fluoronitrofen、CFNP)、氟硫隆(fluothiuron)、氟胺草唑(flupoxam)、氟丙嘧草酯(flupropacil)、四氟丙酸(flupropanate、tetrapion)、四氟丙酸钠(flupropanate-sodium)、氟啶嘧磺隆酸(flupyrsulfuron)、氟啶嘧磺隆(flupyrsulfuron-methyl)、氟啶嘧磺隆钠脱甲基酸(flupyrsulfuron-sodium)、氟啶嘧磺隆钠盐(flupyrsulfuron-methyl-sodium)、氟啶草酮(fluridone)、氟咯草酮(flurochloridone)、氯氟吡氧乙酸(fluroxypyr)、氯氟吡氧乙酸的酯(fluroxypyr-esters)、呋草酮(flurtamone)、嗪草酸(fluthiacet)、嗪草酸甲酯(fluthiacet-methyl)、氟磺胺草醚(fomesafen)、氟磺胺草醚钠盐(fomesafen-sodium)、甲酰胺磺隆(foramsulfuron)、杀木膦(fosamine)、杀木膦铵(fosamine-ammonium)、呋氧草醚(furyloxyfen)、草铵膦(glufosinate)、草铵膦的盐(glufosinate-salts)、精草铵膦(glufosinate-P)、精草铵膦的盐(glufosinate-P-salts)、草甘膦(glyphosate)、草甘膦的盐(glyphosate-salts)、氟氯吡啶酸(halauxifen)、氟氯吡啶酯(halauxifen-methyl)、卤索芬(halosafen)、氯吡嘧磺隆酸(halosulfuron)、氯吡嘧磺隆(halosulfuron-methyl)、卤草定(haloxydine)、氟吡禾灵(haloxyfop)、氟吡禾灵钠盐(haloxyfop-sodium)、氟吡禾灵的酯(haloxyfop-esters)、高效氟吡禾灵(haloxyfop-P)、高效氟吡禾灵的酯(haloxyfop-p-esters)、除莠霉素(herbimycin)、六氯丙酮(hexachloroacetone、HCA)、环嗪酮(hexazinone)、咪草酸(imazamethabenz)、咪草酸甲酯(imazamethabenz-methyl)、甲氧咪草烟(imazamox)、甲氧咪草烟铵盐(imazamox-ammonium)、甲咪唑烟酸(imazapic)、甲咪唑烟酸铵盐(imazapic-ammonium)、咪唑烟酸(imazapyr)、咪唑烟酸异丙基铵(imazapyr-isopropylammonium)、咪唑喹啉酸(imazaquin)、咪唑喹啉酸甲酯(imazaquin-methyl)、咪唑喹啉酸的盐(imazaquin-salts)、咪唑乙烟酸(imazethapyr)、咪唑乙烟酸铵盐(imazethapyr-ammonium)、唑吡嘧磺隆(imazosulfuron)、茚草酮(indanofan)、茚嗪氟草胺(indaziflam)、碘草腈(iodobonil)、甲基碘磺隆酸(iodosulfuron)、甲基碘磺隆酸钠盐(iodosulfuron-sodium)、甲基碘磺隆(iodosulfuron-methyl)、甲基碘磺隆钠盐(iodosulfuron-methyl-sodium)、碘磺隆(iofensulfuron)、碘磺隆钠盐(iofensulfuron-sodium)、碘苯腈(ioxynil)、碘苯腈的盐(ioxynil-salts)、碘苯腈的酯(ioxynil-esters)、抑草津(ipazine)、三唑酰草胺(ipfencarbazone)、丙草定(iprymidam)、丁咪酰胺(isocarbamid)、异草定(isocil、isoprocil)、丁嗪草酮(isomethiozin)、异草完隆(isonoruron)、异丙灵(isopolinate)、异丙乐灵(isopropalin)、异丙隆(isoproturon)、异隆(isouron)、异酰草胺(isoxaben)、氯草酮(isoxachlortole)、异唑草酮(isoxaflutole)、异草醚(isoxapyrifop)、特胺灵(karbutilate)、克螺多(ketospiradox)、克螺多钾盐(ketospiradox-potassium)、乳氟禾草灵(lactofen)、ランコトリオン(lancotrione)、ランコトリオンナトリウム(lancotrione-sodium)、环草定(lenacil)、利谷隆(linuron)、MCPA、MCPA的盐(MCPA-salts)、MCPA的酯(MCPA-esters)、MCPB、MCPB的盐(MCPB-salts)、MCPB的酯(MCPB-esters)、2甲4氯丙酸(mecoprop、MCPP)、2甲4氯丙酸的盐(mecoprop-salts)、2甲4氯丙酸的酯(mecoprop-esters)、精2甲4氯丙酸P(mecoprop-P)、精2甲4氯丙酸的盐(mecoprop-P-salts)、精2甲4氯丙酸的酯(mecoprop-P-esters)、地乐施(medinoterb)、地乐施乙酸酯(medinoterb actate)、苯噻酰草胺(mefenacet)、氟磺酰草胺(mefluidide)、氟磺酰草胺的盐(mefluidide-salts)、灭莠津(mesoprazine)、二磺隆酸(mesosulfuron)、甲基二磺隆(mesosulfuron-methyl)、甲基磺草酮(mesotrione)、威百亩(metam、carbam)、威百亩的盐(metam-salts)、唑酰草胺(metamifop)、苯嗪草酮(metamitron)、吡唑草胺(metazachlor)、双醚氯吡嘧磺隆(metazosulfuron)、二甲哒草伏(metflurazon)、甲基苯噻隆(methabenzthiazuron、methibenzuron)、氟烯硝草(methalpropalin)、灭草唑(methazole)、甲硫苯威(methiobencarb)、灭草脲(methiuron)、醚草酮(methometon)、甲氧丙净(methoprotryne、methoprotryn)、苯草酮(methoxyphenone)、甲硫嘧磺隆(methiopyrisulfuron)、甲硫唑草啉(methiozolin)、叠氮基甲烷(methyl azide)、溴甲烷(methyl bromide)、甲基杀草隆(methyl dymron)、碘甲烷(methyl iodide)、异硫氰酸甲酯(methyl isothiocyanate)、吡喃隆(metobenzuron)、溴谷隆(metobromuron)、异丙甲草胺(metolachlor)、精异丙甲草胺(S-metolachlor)、磺草唑胺(metosulam)、甲氧隆(metoxuron)、嗪草酮(metribuzin)、甲磺隆酸(metsulfuron)、甲磺隆(metsulfuron-methyl)、禾草敌(molinate)、庚酰草胺(monalide)、特唑隆(monisouron)、绿谷隆(monolinuron)、单嘧磺隆(monosulfuron)、单嘧磺隆甲酯(monosulfuron-methyl)、灭草隆(monuron、CMU)、灭草隆TCA(monuron-TCA)、伐草快(morfamquat)、伐草快二氯化物(morfamquat dichloride)、萘丙胺(naproanilide)、敌草胺(napropamide)、R-左旋敌草胺(napropamide-M)、萘草胺(naptalam、NPA)、萘草胺钠盐(naptalam-sodium)、草不隆(neburon)、烟嘧磺隆(nicosulfuron)、氟氯草胺(nipyraclofen)、甲磺乐灵(nitralin)、除草醚(nitrofen、NIP、niclofen)、三氟甲草醚(nitrofluorfen)、氟草敏(norflurazon)、草完隆(noruron、norea)、OCH、油酸(oleic acid)、坪草丹(orbencarb)、嘧苯胺磺隆(orthosulfamuron)、氨磺乐灵(oryzalin)、丙炔草酮(oxadiargyl)、草酮(oxadiazon)、草哒松(oxapyrazon)、草哒松的盐(oxapyrazon-salts)、环氧嘧磺隆(oxasulfuron)、嗪草酮(oxaziclomefone)、乙氧氟草醚(oxyfluorfen)、对氟隆(parafluron)、百草枯(paraquat)、百草枯二氯化物(paraquat dichloride)、百草枯二甲基硫酸酯(paraquat dimetilsulfate)、克草敌(pebulate)、壬酸(pelargonic acid、nonanoic acid)、二甲戊灵(pendimethalin)、五氟磺草胺(penoxsulam)、五氯苯酚(pentachlorophenol)、五氯苯酚钠(sodium pentachlorophenoxide)、五氯苯酚月桂酸酯(pentachlorophenyl laurate)、甲氯酰草胺(pentanochlor、solan、CMMP)、环戊草酮(pentoxazone)、黄草伏(perfluidone)、烯草胺(pethoxamid)、棉胺宁(phenisopham)、甜菜宁(phenmedipham)、甜菜宁乙酯(phenmedipham-ethyl)、酰草隆(phenobenzuron)、氨氯吡啶酸(picloram)、氨氯吡啶酸的盐(picloram-salts)、氨氯吡啶酸的酯(picloram-esters)、氟吡酰草胺(picolinafen)、唑啉草酯(pinoxaden)、哌草磷(piperophos)、叠氮钾(potassium azide)、氰酸钾(potassium cyanate)、丙草胺(pretilachlor)、氟嘧磺隆酸(primisulfuron)、氟嘧磺隆(primisulfuron-methyl)、环丙腈津(procyazine)、氨氟乐灵(prodiamine)、氟唑草胺(profluazol)、环丙氟灵(profluralin)、环苯草酮(profoxydim)、甘扑津(proglinazine)、甘扑津乙酯(proglinazine-ethyl)、扑灭通(prometon)、扑草净(prometryn、prometryne)、毒草胺(propachlor)、敌稗(propanil、DCPA)、草酸(propaquizafop)、扑灭津(propazine)、苯胺灵(propham)、异丙草胺(propisochlor)、丙苯磺酸(propoxycarbazone)、丙苯磺隆(propoxycarbazone-sodium)、丙嗪嘧磺隆(propyrisulfuron)、炔苯酰草胺(propyzamide、pronamide)、甲硫磺乐灵(prosulfalin)、苄草丹(prosulfocarb)、氟磺隆(prosulfuron)、扑灭生(proxan、IPX)、扑灭生钠盐(proxan-sodium)、丙炔草胺(prynachlor)、比达农(pydanon)、双唑草腈(pyraclonil)、吡草醚酸(pyraflufen)、吡草醚(pyraflufen-ethyl)、磺酰草吡唑(pyrasulfotole)、吡唑特(pyrazolynate、pyrazolate)、吡嘧磺隆酸(pyrazosulfuron)、吡嘧磺隆(pyrazosulfuron-ethyl)、苄草唑(pyrazoxyfen)、异丙酯草醚(pyribambenz-isopropyl)、丙酯草醚(pyribambenz-propyl)、嘧啶肟草醚(pyribenzoxim)、稗草丹(pyributicarb)、三氯吡啶醇(pyriclor)、哒嗪醇(pyridafol)、哒草特(pyridate)、环酯草醚(pyriftalid)、嘧草醚酸(pyriminobac)、嘧草醚(pyriminobac-methyl)、嘧氯磺草胺(pyrimisulfan)、嘧草硫醚酸(pyrithiobac)、嘧草硫醚(pyrithiobac-sodium)、派罗克杀草砜(pyroxasulfone)、啶磺草胺(pyroxsulam)、二氯喹啉酸(quinclorac)、二氯喹啉酸二甲基铵(quinclorac-dimethylammonium)、二氯喹啉酸甲酯(quinclorac-methyl)、氯甲喹啉酸(quinmerac)、灭藻醌(quinoclamine、ACN)、克藻胺(quinonamid)、喹禾灵酸(quizalofop)、喹禾灵酸的酯(quizalofop-esters)、精喹禾灵酸(quizalofop-P)、精喹禾灵酸的酯(quizalofop-P-esters)、硫氰苯胺(rhodethanil)、砜嘧磺隆(rimsulfuron)、苯嘧磺草胺(saflufenacil)、另丁津(sebuthylazine)、仲丁通(secbumeton)、烯禾啶(sethoxydim)、环草隆(siduron)、西玛津(simazine、CAT)、西玛通(simeton)、西草净(simetryn、simetryne)、叠氮化钠(sodium azide)、氯酸钠(sodium chlorate)、磺草酮(sulcotrione)、菜草畏(sulfallate、CDEC)、甲磺草胺(sulfentrazone)、甲嘧磺隆酸(sulfometuron)、甲嘧磺隆(sulfometuron-methyl)、磺酰磺隆(sulfosulfuron)、硫酸(sulfuric acid)、吖庚磺酯(sulglycapin)、swep(MCC)、稗草烯(tavron)、TCA(trichloroacetic acid)、TCA的盐(TCA-salts)、TCAエタジル(TCA-ethadyl)、牧草胺(tebutam、butam)、丁噻隆(tebuthiuron)、特糠酯酮(tefuryltrione)、环磺酮(tembotrione)、吡喃草酮(tepraloxydim)、特草定(terbacil)、特草灵(terbucarb、terbutol、MPMC)、特丁草胺(terbuchlor)、特丁通(terbumeton)、特丁津(terbuthylazine)、特丁净(terbutryn)、テトフルピロリメット(tetflupyrolimet)、四氟隆(tetrafluron)、噻吩草胺(thenylchlor)、噻氟隆(thiazafluron)、噻唑烟酸(thiazopyr)、噻二唑草胺(thidiazimin)、噻苯隆(thidiazuron)、噻酮磺隆酸(thiencarbazone)、噻酮磺隆(thiencarbazone-methyl)、噻吩磺隆酸(thifensulfuron)、噻吩磺隆(thifensulfuron-methyl)、禾草丹(thiobencarb、benthiocarb)、氟嘧硫草酯(tiafenacil)、仲草丹(tiocarbazil)、嘧草胺(tioclorim)、トルピラレート(tolpyralate)、苯吡唑草酮(topramezone)、三甲苯草酮(tralkoxydim)、氟酮磺草胺(triafamone)、野麦畏(triallate、tri-allate)、醚苯磺隆(triasulfuron)、三嗪氟草胺(triaziflam)、苯磺隆酸(tribenuron)、苯磺隆(tribenuron-methyl)、杀草畏(tricamba)、三氯吡氧乙酸(triclopyr)、三氯吡氧乙酸的盐(triclopyr-salts)、三氯吡氧乙酸的酯(triclopyr-esters)、灭草环(tridiphane)、草达津(trietazine)、三氟啶磺隆(trifloxysulfuron)、三氟啶磺隆钠盐(trifloxysulfuron-sodium)、トリフルディモキサジン(trifludimoxadin)、氟乐灵(trifluralin)、氟胺磺隆酸(triflusulfuron)、氟胺磺隆(triflusulfuron-methyl)、トリホップ(trifop)、トリホップメチル(trifop-methyl)、三氟禾草肟(trifopsime)、三羟基三嗪(trihydroxytriazine、cyanuric acid)、三甲异脲(trimeturon)、茚草酰(tripropindan)、草达克(tritac)、三氟甲磺隆(tritosulfuron)、灭草敌(vernolate)、二甲苯草胺(xylachlor)、ジメスルファゼット(dimesulfazet)、6-{(二氟甲基)硫基}-N2,N4-二异丙基-1,3,5-三嗪-2,4-二胺(CAS 103427-73-2)、(R)-2-[{7-(2-氯-4-(三氟甲基)苯氧基)萘-2-基}氧基]丙酸甲酯(CAS 103055-25-0)、丙烷-2-酮O-(12H-二苯并[d,g][1,3]二氧杂环辛三烯-6-羰基)肟(CAS503819-68-9)、[{(2-(N-甲基甲基磺酰胺)-2-氧代乙基)氨基}甲基]膦酸(CAS 98565-18-5)、2-[{2-(4-((6-氯喹喔啉-2-基)氧基)苯氧基)丙酰基}氧基]-3-甲基-3-丁烯酸乙酯(CAS 1191932-79-2)、2-(3,7-二氯喹啉-8-羰基)-3-羟基-2-环己烯-1-酮(CAS 1350901-36-8)、O-(2,4-二甲基-6-硝基苯基)O-甲基异丙基硫代磷酰胺(CAS 189517-75-7)、5-[N-{(4,6-二甲基嘧啶-2-基)氨基甲酰基}氨磺酰基]-1-(吡啶-2-基)-1H-吡唑-4-甲酸甲酯(CAS 104770-29-8)、4-[2-氯-3-{(3,5-二甲基-1H-吡唑-1-基)甲基}-4-(甲基磺酰)苯甲酰]-1,3-二甲基-1H-吡唑-5-基1,3-二甲基-1H-吡唑-4-甲酸酯(CAS 1911613-97-2)、4-[2-氯-4-(甲基磺酰)-3-{(2,2,2-三氟乙氧基)甲基}苯甲酰]-1-乙基-1H-吡唑-5-基1,3-二甲基-1H-吡唑-4-甲酸酯(CAS 1992017-55-6)、1-{2-氯-3-(3-环丙基-5-羟基-1-甲基-1H-吡唑-4-羰基)-6-(三氟甲基)苯基}哌啶-2-酮(CAS 1855929-45-1)、1,3-二甲基-4-{2-(甲基磺酰)-4-(三氟甲基)苯甲酰}-1H-吡唑-5-基1,3-二甲基-1H-吡唑-4-甲酸酯(CAS 1622908-18-2)、2-[{3-(2-氯-4-氟-5-(3-甲基-2,6-二氧代-4-(三氟甲基)-3,6-二氢嘧啶-1(2H)-基)苯氧基)吡啶-2-基}氧基]乙酸乙酯(CAS 353292-31-6)、2-甲基-N-(5-甲基-1,3,4-二唑-2-基)-3-(甲基磺酰)-4-(三氟甲基)苯甲酰胺(CAS 1400904-50-8)、2-氯-N-(1-甲基-1H-四唑-5-基)-3-(甲硫基)-4-(三氟甲基)苯甲酰胺(CAS 1361139-71-0)、2-氯-N-(1-甲基-1H-四唑-5-基)-3-(甲基磺酰)-4-(三氟甲基)苯甲酰胺(CAS1361139-73-2)、4-(4-氟苯基)-6-(2-羟基-6-氧代-1-环己烯-1-羰基)-2-甲基-1,2,4-三嗪-3,5(2H、4H)-二酮(CAS 1353870-34-4)、F4050(试验名)、F9960(试验名)、OK-701(试验名)和SL-1201(试验名)等。
安全剂:解草嗪(benoxacor)、BPCMS(CSB)、喹氧乙酸(cloquintocet)、解草酯(cloquintocet-mexyl)、苄草隆(cumyluron)、解草胺腈(cyometrinil)、环丙磺酰胺(cyprosulfamide)、杀草隆(daimuron、dymron)、烯丙酰草胺(dichlormid)、二环酮(dicyclonon、diclonon)、增效磷(dietholate)、哌草丹(dimepiperate)、乙拌磷(disulphoton)、解草唑(fenchlorazole)、解草唑乙酯(fenchlorazole-ethyl)、解草啶(fenclorim)、解草胺(flurazole)、氟草肟(fluxofenim)、解草唑(furilazole)、ヘキシム(hexim)、双苯唑酸(isoxadifen)、双苯唑酯(isoxadifen-ethyl)、MCPA、2甲4氯丙酸(mecoprop)、吡唑解草酸(mefenpyr)、吡唑解草酯(mefenpyr-diethyl)、灭芬酯(mephenate)、メトカミフェン(metcamifen)、苯草酮(methoxyphenone)、1,8-萘二甲酸酐(naphthalic anhydride、NA)、辛二胺(octamethylene-diamine)、解草腈(oxabetrinil)、4-(二氯乙酰)-1-氧杂-4-氮杂螺[4.5]癸烷(AD67、MON4660)、4-羧基-3,4-二氢-2H-1-苯并吡喃-4-乙酸(CL304415)、2,2-二氯-N-[2-氧代-2-(丙烯基氨基)乙基]-N-2-丙烯基乙酰胺(DKA-24)、2-(二氯甲基)-2-甲基-1,3-二氧戊环(MG191)、2-丙烯基1-氧杂-4-氮杂螺[4,5]癸烷-4-二硫代甲酸酯(MG838)、(3-二氯乙酰-5-(2-呋喃基)-2,2-二甲基唑烷)(MON13900)、(N-烯丙基-N-[(1,3-二氧戊环-2-基)甲基]二氯乙酰胺(PPG-1292)、3-(二氯乙酰)-2,2-二甲基-1,3-唑烷(R28725)、3-(二氯乙酰)-2,2,5-三甲基-1,3-唑烷(R29148)和1-二氯乙酰氮杂环庚烷(TI-35)等。
杀菌剂:活化酯(acibenzolar-S-methyl)、八九十混酸(acypetacs)、艾敌吗啉(aldimorph)、烯丙醇(allyl alcohol)、唑嘧菌胺(ametoctradin)、アミノピリフェン(aminopyrifen)、吲唑磺菌胺(amisulbrom)、代森铵(amobam)、氨丙膦酸(ampropylfos)、敌菌灵(anilazine)、氧环唑(azaconazole)、氧化福美双(azithiram)、嘧菌酯(azoxystrobin)、多硫化钡(barium polysulfide)、苯霜灵(benalaxyl)、高效苯霜灵(benalaxyl-M)、麦锈灵(benodanil)、苯菌灵(benomyl)、醌肟腙(benquinox)、丙唑草隆(bentaluron)、苯噻菌胺酯(benthiavalicarb-isopropyl)、苯噻硫氰(benthiazole)、节烯酸(benzamacril)、抑菌啉(benzamorf)、苯并烯氟菌唑(benzovindiflupyr)、乐杀螨(binapacryl)、联苯(biphenyl)、联苯三唑醇(bitertanol)、联苯吡菌胺(bixafen)、灰瘟素(blasticidin-S)、波尔多液(bordeaux mixture)、烟酰胺(boscalid)、糠菌唑(bromoconazole)、乙嘧酚磺酸酯(bupirimate)、丁硫啶(buthiobate)、丁基胺(butylamine)、石硫合剂(calcium polysulfide)、敌菌丹(captafol)、克菌丹(captan)、吗菌威(carbamorph)、多菌灵(carbendazim)、萎锈灵(carboxin)、环丙酰菌胺(carpropamid)、香芹酮(carvone)、切欣特混合液(cheshunt mixture)、灭螨猛(chinomethionat)、灭瘟唑(chlobenthiazone)、双胺灵(chloraniformethane)、四氯苯醌(chloranil)、苯咪唑菌(chlorfenazole)、氯苯甲醚(chloroneb)、氯化苦(chloropicrin)、百菌清(chlorothalonil)、四氯喹啉(chlorquinox)、乙菌利(chlozolinate)、咪菌酮(climbazole)、乙酸铜(copper acetate)、碱式碳酸铜(copper carbonate,basic)、氢氧化铜(copper hydroxide)、环烷酸铜(copper naphthenate)、油酸铜(copper oleate)、王铜(copper oxychloride)、硫酸铜(copper sulfate)、碱式硫酸铜(copper sulfate、basic)、铬酸铜锌(copper zinc chromate)、丁香菌酯(coumoxystrobin)、甲酚(cresol)、硫杂灵(cufraneb)、福美铜氯(cuprobam)、氰霜唑(cyazofamid)、环菌胺(cyclafuramid)、放线菌酮(cycloheximide)、环氟苄酰胺(cyflufenamid)、霜脲氰(cymoxanil)、氰菌灵(cypendazole)、环丙唑醇(cyproconazole)、嘧菌环胺(cyprodinil)、酯菌胺(cyprofuram)、棉隆(dazomet)、咪菌威(debacarb)、癸磷锡(decafentin)、脱氢乙酸(dehydroacetic acid)、ジクロベンチアゾクス(dichlobentiazox)、苯氟磺胺(dichlofluanid)、二氯萘醌(dichlone)、双氯酚(dichlorophen)、菌核利(dichlozoline)、苄氯三唑醇(diclobutrazol)、双氯氰菌胺(diclocymet)、哒菌酮(diclomezine)、氯硝胺(dicloran)、乙霉威(diethofencarb)、苯醚甲环唑(difenoconazole)、氟嘧菌胺(diflumetorim)、二甲嘧酚(dimethirimol)、烯酰吗啉(dimethomorph)、醚菌胺(dimoxystrobin)、烯唑醇(diniconazole)、高效烯唑醇(diniconazole-M)、消螨通(dinobuton)、二硝巴豆酚酯(dinocap)、二硝巴豆酚酯-4(dinocap-4)、二硝巴豆酚酯-6(dinocap-6)、二硝酯(dinocton)、硝辛酯(dinosulfon)、硝丁酯(dinoterbon)、二苯基胺(diphenylamine)、ジピメチトロン(dipymetitrone)、吡菌硫(dipyrithione)、双硫仑(disulfiram)、灭菌磷(ditalimfos)、二氰蒽醌(dithianon)、4,6-二硝基邻甲酚(DNOC)、十二环吗啉(dodemorph)、多果定(dodine)、肼菌酮(drazoxolon)、敌瘟磷(edifenphos)、烯肟菌酯(enestrobin)、エノキサストロビン(enoxastrobin)、氟环唑(epoxiconazole)、噻唑菌胺(ethaboxam)、乙环唑(etaconazole)、代森硫(etem)、乙嘧酚(ethirimol)、乙氧喹啉(ethoxyquin)、土菌灵(etridiazole)、唑菌酮(famoxadone)、咪唑菌酮(fenamidone)、敌磺钠(fenaminosulf)、烯肟菌胺(fenaminstrobin)、咪菌腈(fenapanil)、氯苯嘧啶醇(fenarimol)、腈苯唑(fenbuconazole)、甲呋酰胺(fenfuram)、环酰菌胺(fenhexamid)、种衣酯(fenitropan)、稻瘟酰胺(fenoxanil)、拌种咯(fenpiclonil)、フェンピコキサミド(fenpicoxamid)、苯锈啶(fenpropidin)、丁苯吗啉(fenpropimorph)、胺苯吡菌酮(fenpyrazamine)、三苯锡(fentin)、福美铁(ferbam)、嘧菌腙(ferimzone)、吡啶菌酰胺(florylpicoxamid)、氟啶胺(fluazinam)、咯菌腈(fludioxonil)、氟菌螨酯(flufenoxystrobin)、氟茚唑菌胺(fluindapyr)、氟酰菌胺(flumetover)、氟吗啉(flumorph)、氟吡菌胺(fluopicolide)、氟醚菌酰胺(fluopimomide)、氟吡菌酰胺(fluopyram)、氟氯菌核利(fluoroimide)、三氟苯唑(fluotrimazole)、フルオキサピプロリン(fluoxapiprolin)、氟嘧菌酯(fluoxastrobin)、氟喹唑(fluquinconazole)、氟硅唑(flusilazole)、磺菌胺(flusulfamide)、氟酰胺(flutolanil)、氟噻菌净(flutianil)、粉唑醇(flutriafol)、氟唑菌酰胺(fluxapyroxad)、灭菌丹(folpet)、三乙膦酸铝(fosetyl-aluminium)、四氯苯酞(fthalide)、麦穗宁(fuberidazole)、呋霜灵(furalaxyl)、呋吡菌胺(furametpyr)、二甲呋酰胺(furcarbanil)、呋菌唑(furconazole)、呋醚唑(furconazole-cis)、拌种胺(furmecyclox)、呋菌隆(furophanate)、果绿啶(glyodin)、灰荑霉素(griseofulvin)、双胍辛盐(guazatine)、丙烯酸喹啉酯(halacrinate)、六氯苯(hexachlorobenzene)、己唑醇(hexaconazole)、环己硫磷(hexylthiofos)、8-羟基喹啉硫酸盐(8-hydroxyquinoline sulfate)、霉灵(hymexazol)、抑霉唑(imazalil)、亚胺唑(imibenconazole)、双胍辛烷基苯磺酸盐(iminoctadine-albesilate)、双胍辛胺乙酸盐(iminoctadine-triacetate)、インピルフルキサム(inpyrfluxam)、碘代丙炔基丁基氨基甲酸酯(iodocarb)、种菌唑(ipconazole)、イプフェントリフルコナゾール(ipfentrifluconazole)、イプフルフェノキン(ipflufenoquin)、异稻瘟净(iprobenfos)、异菌脲(iprodione)、缬霉威(iprovalicarb)、异丙噻菌胺(isofetamid)、イソフルシプラム(isoflucypram)、异噻菌胺(isotianil)、稻瘟灵(isoprothiolane)、吡唑萘菌胺(isopyrazam)、氯苯咪菌酮(isovaledione)、春雷霉素(kasugamycin)、醚菌酯(kresoxim-methyl)、昆布糖(laminarin)、代森锰铜(mancopper)、代森锰锌(mancozeb)、甲哌喹(mandestrobin)、双炔酰菌胺(mandipropamid)、代森锰(maneb)、邻酰胺(mebenil)、苯并威(mecarbinzid)、氯氟醚菌唑(mefentrifluconazole)、嘧菌胺(mepanipyrim)、灭锈胺(mepronil)、消螨多(meptyldinocap)、甲霜灵(metalaxyl)、高效甲霜灵(metalaxyl-M)、威百亩(metam)、间氯敌菌酮(metazoxolon)、叶菌唑(metconazole)、磺菌威(methasulfocarb)、呋菌胺(methfuroxam)、メチルテトラプロール(metyltetraprole)、代森联(metiram)、苯氧菌胺(metominostrobin)、苯菌酮(metrafenone)、噻菌胺(metsulfovax)、代森环(milneb)、腈菌唑(myclobutanil)、甲菌利(myclozolin)、代森钠(nabam)、萘替芬(naftifine)、那他霉素(natamycin)、有机镍(nickel bis(dimethyldithiocarbamate))、硫氰散(nitrostyrene)、酞菌酯(nitrothal-isopropyl)、氟苯嘧啶醇(nuarimol)、辛噻酮(octhilinone)、呋酰胺(ofurace)、肟醚菌胺(orysastrobin)、霜灵(oxadixyl)、氟噻唑吡乙酮(oxathiapiprolin)、喹啉铜(oxinecopper)、咪唑富马酸盐(oxpoconazole fumarate)、氧化萎锈灵(oxycarboxin)、稻瘟酯(pefurazoate)、戊菌唑(penconazole)、戊菌隆(pencycuron)、氟唑菌苯胺(penflufen)、五氯苯酚(pentachlorophenol)、吡噻菌胺(penthiopyrad)、邻苯基苯酚(2-phenylphenol)、氯瘟磷(phosdiphen)、四氯苯酞(phthalide)、四唑吡氨酯(picarbutrazox)、啶氧菌酯(picoxystrobin)、病花灵(piperalin)、代森福美锌(polycarbamate)、多抗霉素(polyoxins)、多氧霉素-D(polyoxorim)、叠氮钾(potassium azide)、碳酸氢钾(potassiumhydrogen carbonate)、烯丙苯噻唑(probenazole)、咪鲜胺(prochloraz)、腐霉利(procymidone)、霜霉威盐酸盐(propamocarb hydrochloride)、丙环唑(propiconazole)、丙森锌(propineb)、丙氧喹啉(proquinazid)、硫菌威(prothiocarb)、吡菌磷(pyrazophos)、吡菌苯威(pyribencarb)、啶斑肟(pyrifenox)、嘧霉胺(pyrimethanil)、嘧螨胺(pyriminostrobin)、咯喹酮(pyroquilon)、硫菌威(prothiocarb)、丙硫菌唑(prothioconazole)、氟唑菌酰羟胺(pydiflumetofen)、吡喃灵(pyracarbolid)、吡唑醚菌酯(pyraclostrobin)、唑胺菌酯(pyrametostrobin)、唑菌酯(pyraoxystrobin)、氟醚菌酰胺(pyrapropoyne)、联苯吡嗪菌胺(pyraziflumid)、ピリダクロメチル(pyridachlometyl)、啶菌腈(pyridinitril)、苯啶菌酮(pyriofenone)、啶菌唑(pyrisoxazole)、氯甲氧吡啶(pyroxychlor)、氯吡根呋醚(pyroxyfur)、喹菌盐(quinacetol-sulfate)、醌菌腙(quinazamid)、キンコナゾール(quinconazole)、苯氧喹啉(quinoxyfen)、キノフメリン(quinofumelin)、五氯硝基苯(quintozene)、吡咪唑(rabenzazole)、水杨苯胺(salicylanilide)、氟唑环菌胺(sedaxane)、硅噻菌胺(silthiofam)、硅氟唑(simeconazole)、碳酸氢钠(sodium hydrogen carbonate)、次氯酸钠(sodiumhypochlorite)、螺环菌胺(spiroxamine)、硫(sulfur)、戊唑醇(tebuconazole)、异丁乙氧喹啉(tebufloquin)、叶枯酞(tecloftalam)、四氯硝基苯(tecnazene)、福代硫(tecoram)、四氟醚唑(tetraconazole)、噻菌灵(thiabendazole)、噻二氟(thiadifluor)、噻菌腈(thicyofen)、噻氟菌胺(thifluzamide)、灭菌酞胺(thiochlorfenphim)、硫菌灵(thiophanate)、甲基硫菌灵(thiophanate-methyl)、福美双(thiram)、噻酰菌胺(tiadinil)、硫氰苯甲酰胺(tioxymid)、甲基立枯磷(tolclofos-methyl)、三氟甲氧威(tolprocarb)、甲苯氟磺胺(tolylfluanid)、三唑酮(triadimefon)、三唑醇(triadimenol)、威菌磷(triamiphos)、嘧菌醇(triarimol)、叶锈特(triazbutil)、咪唑嗪(triazoxide)、三丁基氧化锡(tributyltin oxide)、水杨菌胺(trichlamide)、氯啶菌酯(triclopyricarb)、三环唑(tricyclazole)、十三吗啉(tridemorph)、肟菌酯(trifloxystrobin)、氟菌唑(triflumizole)、嗪氨灵(triforine)、灭菌唑(triticonazole)、有效霉素(validamycin)、缬菌胺(valifenalate)、乙烯菌核利(vinclozolin)、氰菌胺(zarilamid)、环烷酸锌(zinc naphthenate)、氟苯醚酰胺(flubeneteram)、硫酸锌(zinc sulfate)、代森锌(zineb)、福美锌(ziram)、苯酰菌胺(zoxamide)、香菇菌丝体提取物(shiitake mycelium extract)和香菇子实体提取物(shiitake fruiting body extract)等。
杀线虫剂:涕灭砜威(aldoxycarb)、ベンクロチアズ(benclothiaz)、硫线磷(cadusafos)、二溴氯丙烷(DBCP)、除线磷(dichlofenthion)、多果定(DSP)、灭线磷(ethoprophos)、苯线磷(fenamiphos)、丰索磷(fensulfothion)、三氟咪啶酰胺(fluazaindolizine)、联氟砜(fluensulfone)、噻唑膦(fosthiazate)、丁硫环磷(fosthietan)、新烟磷(imicyafos)、イサミドホス(isamidofos)、氯唑磷(isazofos)、杀线威(oxamyl)、チオキサザフェン(thiaxazafen)、虫线磷(thionazin)、チオキサザフェン(tioxazafen)和シクロブトリフルラム(cyclobutrifluram)等。
杀虫剂:阿维菌素(abamectin)、乙酰甲胺磷(acephate)、灭螨醌(acequinocyl)、啶虫脒(acetamiprid)、氟丙菊酯(acrinathrin)、アシノナピル(acynonapyr)、双丙环虫酯(afidopyropen)、阿福拉纳(afoxolaner)、棉铃威(alanycarb)、涕灭威(aldicarb)、烯丙菊酯(allethrin)、顺式氯氰菊酯(alpha-cypermethrin)、α-硫丹(alpha-endosulfan)、磺胺螨酯(amidoflumet)、双甲脒(amitraz)、甲基吡磷(azamethiphos)、益棉磷(azinphos-ethyl)、保棉磷(azinphos-methyl)、三唑锡(azocyclotin)、苏云金芽孢杆菌(bacillusthuringiensis)、虫威(bendiocarb)、四氟苯菊酯(benfluthrin)、丙硫克百威(benfuracarb)、杀虫磺(bensultap)、苯螨特(benzoximate)、ベンズピリモキサン(benzpyrimoxan)、高效氟氯氰菊酯(beta-cyfluthrin)、高效氯氰菊酯(beta-cypermethrin)、联苯肼酯(bifenazate)、联苯菊酯(bifenthrin)、生物烯丙菊酯(bioallethrin)、生物苄呋菊酯(bioresmethrin)、双三氟虫脲(bistrifluron)、溴虫氟苯双酰胺(broflanilide)、溴螨酯(bromopropylate)、噻嗪酮(buprofezin)、丁酮威(butocarboxim)、甲萘威(carbaryl)、克百威(carbofuran)、丁硫克百威(carbosulfan)、杀螟丹(cartap)、灭螨猛(chinomethionat)、氯虫酰胺(chlorantraniliprole)、氯氧磷(chlorethxyfos)、虫螨腈(chlorfenapyr)、毒虫畏(chlorfenvinphos)、氟啶脲(chlorfluazuron)、氯甲硫磷(chlormephos)、乙酯杀螨醇(chlorobezilate)、右旋反式氯炔丙菊酯(chloroprallethrin)、毒死蜱(chlorpyrifos)、甲基毒死蜱(chlorpyrifos-methyl)、环虫酰肼(chromafenozide)、四螨嗪(clofentezine)、噻虫胺(clothianidin)、杀螟腈(cyanophos)、氰虫酰胺(cyantraniliprole)、环溴虫酰胺(cyclaniliprole)、乙氰菊酯(cycloprothrin)、腈吡螨酯(cyenopyrafen)、丁氟螨酯(cyflumetofen)、丁氟螨酯(cyflumetofen)、氟氯氰菊酯(cyfluthrin)、氯氟氰虫酰胺(cyhalodiamide)、氯氟氰菊酯(cyhalothrin)、三环锡(cyhexatine)、氯氰菊酯(cypermethrin)、苯醚氰菊酯(cyphenothrin)、灭蝇胺(cyromazine)、溴氰菊酯(deltamethrin)、噻虫嗪(diacloden)、丁醚脲(diafenthiuron)、二嗪磷(diazinon)、敌敌畏(dichlorvos)、ジクロロメゾチアズ(dicloromezotiaz)、三氯杀螨醇(dicofol)、遍地克(dienochlor)、氟螨嗪(diflovidazin)、除虫脲(diflubenzuron)、四氟甲醚菊酯(dimefluthrin)、乐果(dimethoate)、甲基毒虫畏(dimethylvinphos)、呋虫胺(dinotefuran)、苯虫醚(diofenolan)、乙拌磷(disulfoton)、4,6-二硝基邻甲酚(DNOC)、d-T-80-胺菊酯(d-tetramethrin)、甲氨基阿维菌素苯甲酸盐(emamectin-benzoate)、右旋烯炔菊酯(empenthrin)、硫丹(endosulfan)、苯硫膦(EPN)、ε-甲氧苄氟菊酯(epsilon-metofluthrin)、イプシロン-モムフルオロトリン(epsilon-momfluorothrin)、高氰戊菊酯(esfenvalerate)、乙硫苯威(ethiofencarb)、乙虫腈(ethiprole)、醚菊酯(etofenprox)、乙螨唑(etoxazole)、乙嘧硫磷(etrimfos)、非班太尔(Febantel)、喹螨醚(fenazaquin)、苯丁锡(fenbutatin oxide)、杀螟硫磷(fenitrothion)、仲丁威(fenobucarb)、苯硫威(fenothiocarb)、苯氧威(fenoxycarb)、甲氰菊酯(fenpropathrin)、甲氰菊酯(fenpropathrin)、唑螨酯(fenpyroximate)、倍硫磷(fenthion)、氰戊菊酯(fenvalerate)、氟虫腈(fipronil)、フロメトキン(flometoquin)、氟啶虫酰胺(flonicamid)、嘧螨酯(fluacrypyrim)、啶蜱脲(fluazuron)、氟虫酰胺(flubendiamide)、氟环脲(flucycloxuron)、氟氰戊菊酯(flucythrinate)、嘧虫胺(flufenerim)、氟虫脲(flufenoxuron)、三氟醚菊酯(flufenprox)、丁烯氟虫腈(flufiprole)、フルヘキサホン(fluhexafon)、氟氯苯菊酯(flumethrin)、氟吡呋喃酮(flupyradifurone)、フルピリミン(flupyrimin)、氟氰虫酰胺(fluralaner)、氟胺氰菊酯(fluvalinate)、フルキサメタミド(fluxametamide)、地虫硫磷(fonophos)、伐虫脒(formetanate)、安硫磷(formothion)、呋线威(furathiocarb)、精高效氯氟氰菊酯(gamma-cyhalothrin)、苄螨醚(halfenprox)、氯虫酰肼(halofenozide)、七氟甲醚菊酯(heptafluthrin)、氟铃脲(hexaflumuron)、噻螨酮(hexythiazox)、氟蚁腙(hydramethylnon)、吡虫啉(imidacloprid)、炔咪菊酯(imiprothrin)、茚虫威(indoxacarb)、茚虫威-MP(indoxacarb-MP)、异唑虫酰胺(isocycloseram)、异柳磷(isofenphos)、异丙威(isoprocarb)、唑磷(isoxathion)、R-联苯菊酯(kappa-bifenthrin)、R-七氟菊酯(kappa-tefluthrin)、高效氯氟氰菊酯(lambda-cyhalothrin)、雷皮菌素(lepimectin)、虱螨脲(lufenuron)、马拉硫磷(malathion)、氯氟醚菊酯(meperfluthrin)、氰氟虫腙(metaflumizone)、速灭威(metalcarb)、四聚乙醛(metaldehyde)、虫螨畏(methacrifos)、甲胺磷(methamidophos)、杀扑磷(methidathion)、灭多威(methomyl)、烯虫酯(methoprene)、甲氧滴滴涕(methoxychlor)、甲氧虫酰肼(methoxyfenozide)、溴甲烷(methyl bromide)、甲氧苄氟菊酯(metofluthrin)、弥拜菌素(milbemectin)、モムフルオロトリン(momfluorothrin)、久效磷(monocrotophos)、诱虫烯(muscalure)、烯啶虫胺(nitenpyram)、氟酰脲(novaluron)、多氟脲(noviflumuron)、氧乐果(omethoate)、オキサゾスルフィル(oxazosulfyl)、亚砜磷(oxydemeton-methyl)、异亚砜磷(oxydeprofos)、对硫磷(parathion)、甲基对硫磷(parathion-methyl)、五氯苯酚(pentachlorophenol)、氯菊酯(permethrin)、苯醚菊酯(phenothrin)、稻丰散(phenthoate)、甲拌磷(phorate)、伏杀硫磷(phosalone)、亚胺硫磷(phosmet)、磷胺(phosphamidon)、辛硫磷(phoxim)、抗蚜威(pirimicarb)、甲基嘧啶磷(pirimiphos-methyl)、吡喹酮(Praziquantel)、丙溴磷(profenofos)、丙氟菊酯(profluthrin)、丙虫磷(propaphos)、快螨特(propargite)、丙硫磷(prothiofos)、氟苯醚菊酯(protrifenbute)、吡唑酰苯胺(pyflubumide)、吡蚜酮(pymetrozine)、吡唑硫磷(pyraclofos)、啶吡唑虫胺(pyrafluprole)、除虫菊素(pyrethrins)、哒螨灵(pyridaben)、啶虫醚(pyridalyl)、吡氟喹虫唑(pyrifluquinazon)、嘧螨醚(pyrimidifen)、吡啶氟虫腈(pyriprole)、吡丙醚(pyriproxyfen)、苄呋菊酯(resmethrin)、鱼藤酮(rotenone)、氟硅菊酯(silafluofen)、乙基多杀菌素(spinetoram)、多杀霉素(spinosad)、螺螨酯(spirodiclofen)、螺虫酯(spiromesifen)、甲氧哌啶乙酯(spiropidion)、螺虫乙酯(spirotetramat)、螺虫酯(spyromesifen)、治螟磷(sulfotep)、砜虫啶(sulfoxaflor)、硫丙磷(sulprofos)、τ-氟胺氰菊酯(tau-fluvalinate)、虫酰肼(tebfenozide)、吡螨胺(tebufenpyrad)、氟苯脲(teflubenzuron)、七氟菊酯(tefluthorin)、特丁硫磷(terbufos)、四氯虫酰胺(tetrachlorantraniliprole)、杀虫畏(tetrachlorvinphos)、胺菊酯(tetramethrin)、四氟醚菊酯(tetramethylfluthrin)、氟氰虫酰胺(tetraniliprole)、噻虫啉(thiacloprid)、噻虫嗪(thiamethoxam)、杀虫环(thiocyclam)、硫双威(thiodicarb)、久效威(thiofanox)、甲基乙拌磷(thiometon)、唑虫酰胺(tolfenpyrad)、四溴菊酯(tralomethrin)、四氟苯菊酯(transfluthrin)、唑蚜威(triazamate)、唑蚜威(triazuron)、敌百虫(trichlorfon)、三氟苯嘧啶(triflumezopyrim)、杀铃脲(triflumuron)、チクロピラゾフロル(tyclopyrazoflor)、蚜灭磷(vamidothion)、zeta-氯氰菊酯(zeta-cypermethrin)、フルペンチオフェノックス(flupentiofenox)和乙唑螨腈(cyetpyrafen)等。
在本发明组合物中,也可以根据需要加入表面活性剂。作为这些表面活性剂,可举出以下的(A)、(B)、(C)、(D)和(E)。
(A)非离子性表面活性剂:
(A-1)聚乙二醇型表面活性剂:例如,聚氧乙烯烷基(例如C8~18)醚、烷基萘酚的氧化乙烯加成物、聚氧乙烯(单或二)烷基(例如C8~12)苯基醚、聚氧乙烯(单或二)烷基(例如C8~12)苯基醚的甲醛缩合物、聚氧乙烯(单、二或三)苯基苯基醚、聚氧乙烯(单、二或三)苄基苯基醚、聚氧丙烯(单、二或三)苄基苯基醚、聚氧乙烯(单、二或三)苯乙烯基苯基醚、聚氧丙烯(单、二或三)苯乙烯基苯基醚、聚氧乙烯(单、二或三)苯乙烯基苯基醚的聚合物、聚氧乙烯聚氧丙烯(单、二或三)苯乙烯基苯基醚、聚氧乙烯聚氧丙烯嵌段聚合物、烷基(例如C8~18)聚氧乙烯聚氧丙烯嵌段聚合物醚、烷基(例如C8~12)苯基聚氧乙烯聚氧丙烯嵌段聚合物醚、聚氧乙烯双苯基醚、聚氧乙烯树脂酸酯、聚氧乙烯脂肪酸(例如C8~18)单酯、聚氧乙烯脂肪酸(例如C8~18)二酯、聚氧乙烯失水山梨糖醇(单、二或三)脂肪酸(例如C8~18)酯、甘油脂肪酸酯氧化乙烯加成物、蓖麻油氧化乙烯加成物、氢化蓖麻油氧化乙烯加成物、烷基(例如C8~18)胺氧化乙烯加成物和脂肪酸(例如C8~18)酰胺氧化乙烯加成物等。
(A-2)多元醇型表面活性剂:例如,甘油脂肪酸酯、聚甘油脂肪酸酯、季戊四醇脂肪酸酯、山梨糖醇脂肪酸(例如C8~18)酯、失水山梨糖醇(单、二或三)脂肪酸(例如C8~18)酯、蔗糖脂肪酸酯、多元醇烷基醚、烷基糖苷、烷基多糖苷和脂肪酸链烷醇酰胺等。
(A-3)炔系表面活性剂:例如,炔属二醇、炔属醇、炔属二醇的氧化乙烯加成物和炔属醇的氧化乙烯加成物等。
(B)阴离子性表面活性剂:
(B-1)羧酸型表面活性剂:例如,聚丙烯酸、聚甲基丙烯酸、聚马来酸、聚马来酸酐、马来酸或马来酸酐与烯烃(例如异丁烯和二异丁烯等)的共聚物、丙烯酸与衣康酸的共聚物、甲基丙烯酸与衣康酸的共聚物、马来酸或马来酸酐与苯乙烯的共聚物、丙烯酸与甲基丙烯酸的共聚物、丙烯酸与丙烯酸甲酯的共聚物、丙烯酸与乙酸乙烯酯的共聚物、丙烯酸与马来酸或马来酸酐的共聚物、聚氧乙烯烷基(例如C8~18)醚乙酸、N-甲基-脂肪酸(例如C8~18)肌氨酸酯、树脂酸和脂肪酸(例如C8~18)等羧酸、以及这些羧酸的盐。
(B-2)硫酸酯型表面活性剂:例如,烷基(例如C8~18)硫酸酯、聚氧乙烯烷基(例如C8~18)醚硫酸酯、聚氧乙烯(单或二)烷基(例如C8~12)苯基醚硫酸酯、聚氧乙烯(单或二)烷基(例如C8~12)苯基醚的聚合物的硫酸酯、聚氧乙烯(单、二或三)苯基苯基醚硫酸酯、聚氧乙烯(单、二或三)苄基苯基醚硫酸酯、聚氧乙烯(单、二或三)苯乙烯基苯基醚硫酸酯、聚氧乙烯(单、二或三)苯乙烯基苯基醚的聚合物的硫酸酯、聚氧乙烯聚氧丙烯嵌段聚合物的硫酸酯、硫酸化油、硫酸化脂肪酸酯、硫酸化脂肪酸和硫酸化烯烃等硫酸酯、以及这些硫酸酯的盐。
(B-3)磺酸型表面活性剂:例如,石蜡(例如C8~22)磺酸、烷基(例如C8~12)苯磺酸、烷基(例如C8~12)苯磺酸的甲醛缩合物、甲酚磺酸的甲醛缩合物、α-烯烃(例如C8~16)磺酸、二烷基(例如C8~12)磺基琥珀酸、木质素磺酸、聚氧乙烯(单或二)烷基(例如C8~12)苯基醚磺酸、聚氧乙烯烷基(例如C8~18)醚磺基琥珀酸半酯、萘磺酸、(单或二)烷基(例如C1~6)萘磺酸、萘磺酸的甲醛缩合物、(单或二)烷基(例如C1~6)萘磺酸的甲醛缩合物、杂酚油磺酸的甲醛缩合物、烷基(例如C8~12)二苯基醚二磺酸、イゲポンT(商品名)、聚苯乙烯磺酸和苯乙烯磺酸与甲基丙烯酸的共聚物等磺酸、以及这些磺酸的盐。
(B-4)磷酸酯型表面活性剂:例如,烷基(例如C8~12)磷酸酯、聚氧乙烯烷基(例如C8~18)醚磷酸酯、聚氧乙烯(单或二)烷基(例如C8~12)苯基醚磷酸酯、聚氧乙烯(单、二或三)烷基(例如C8~12)苯基醚的聚合物的磷酸酯、聚氧乙烯(单、二或三)苯基苯基醚磷酸酯、聚氧乙烯(单、二或三)苄基苯基醚磷酸酯、聚氧乙烯(单、二或三)苯乙烯基苯基醚磷酸酯、聚氧乙烯(单、二或三)苯乙烯基苯基醚的聚合物的磷酸酯、聚氧乙烯聚氧丙烯嵌段聚合物的磷酸酯、磷脂酰胆碱、磷脂酰乙醇亚胺和缩合磷酸(例如三聚磷酸等)等的磷酸酯、以及这些磷酸酯的盐。
作为上述(B-1)~(B-4)中的盐的抗衡离子,可举出碱金属(锂、钠和钾等)、碱土金属(钙和镁等)、铵和各种胺(例如烷基胺、环烷基胺和链烷醇胺等)等。
(C)阳离子性表面活性剂:
例如,烷基胺、烷基季铵盐、烷基胺的氧化乙烯加成物和烷基季铵盐的氧化乙烯加成物等。
(D)两性表面活性剂:
(D-1)甜菜碱型表面活性剂:可举出例如,烷基(例如C8~18)二甲基氨基乙酸甜菜碱、酰基(例如C8~18)氨基丙基二甲基氨基乙酸甜菜碱、烷基(例如C8~18)羟基磺基甜菜碱和2-烷基(例如C8~18)-N-羧基甲基-N-羟基乙基咪唑啉甜菜碱。
(D-2)氨基酸型表面活性剂:可举出例如,烷基(例如C8~18)氨基丙酸、烷基(例如C8~18)氨基二丙酸和N-酰基(例如C8~18)-N‘-羧基乙基-N‘-羟基乙基乙二胺。
(D-3)氧化胺型表面活性剂:可举出例如,烷基(例如C8~18)二甲基氧化胺和酰基(例如C8~18)氨基丙基二甲基氧化胺等。
(E)其它表面活性剂:
(E-1)硅系表面活性剂:可举出例如,聚氧乙烯/甲基聚硅氧烷共聚物、聚氧丙烯/甲基聚硅氧烷共聚物和聚(氧乙烯/氧丙烯)/甲基聚硅氧烷共聚物等。
(E-2)氟系表面活性剂:可举出例如,全氟烯基苯磺酸盐、全氟烷基磺酸盐、全氟烷基羧酸盐、全氟烯基聚氧乙烯醚、全氟烷基聚氧乙烯醚和全氟烷基三甲基铵盐等。
这些表面活性剂可以单独使用或混合使用2种以上,进行混合的情况下的比也可以自由选择。本发明组合物中的该表面活性剂的含量可以适当选择,但相对于本发明组合物100重量份优选为0.1~20重量份的范围。
在本发明组合物中,可以进一步含有各种辅助剂。作为可以使用的辅助剂,有增稠剂、有机溶剂、防冻剂、消泡剂、防菌防霉剂和着色剂等,可举出下述物质。
作为增稠剂,没有特别限制,可以使用有机、无机的天然物、合成品和半合成品,可以例示例如,黄原胶(黄原酸胶)、威兰胶和中性树胶等杂多糖类、聚乙烯醇、聚乙烯吡咯烷酮、聚丙烯酸、聚丙烯酸钠和聚丙烯酰胺等水溶性高分子化合物、甲基纤维素、羧基甲基纤维素、羧基乙基纤维素、羟基乙基纤维素和羟基丙基纤维素等纤维素衍生物、蒙脱石、皂石、锂蒙脱石、膨润土、合成锂皂石和合成蒙皂石等蒙皂石系粘土矿物等。这些增稠剂可以使用1种或混合2种以上,进行混合的情况下的比也可以自由选择。这些增稠剂可以直接添加,此外也可以添加预先分散于水而得的物质。此外,本发明组合物中的含量也可以自由选择。
作为有机溶剂,可举出例如乙二醇、二甘醇、丙二醇、双丙甘醇和异丙醇等醇类、丁基溶纤剂等醚、环己酮等酮、γ-丁内酯等酯、N-甲基吡咯烷酮和N-辛基吡咯烷酮等酸酰胺、二甲苯、烷基苯、苯基二甲苯基乙烷和烷基萘等芳香族烃、机械油、正链烷烃、异链烷烃和环烷烃等脂肪族烃、煤油等芳香族烃与脂肪族烃的混合物、豆油、亚麻籽油、菜籽油、椰油、棉籽油和蓖麻油等油脂。
作为防冻剂,可以使用例如乙二醇、二甘醇和丙二醇、甘油等。优选为丙二醇、甘油。此外,本发明组合物中的含量也可以自由选择。
可以进一步混配有机硅系乳液等消泡剂、防菌防霉剂和着色剂等。
本发明组合物的制造方法没有特别限定,可以通过在分散介质中加入上述各成分,利用搅拌机进行混合而获得。此外,根据需要,农药活性成分、表面活性剂和其它辅助剂可以分别单独或混合而利用干式和湿式粉碎机进行微粉碎。
干式粉碎可以用锤磨机、销棒粉碎机、喷射磨机、球磨机或辊磨机等进行。采用湿式粉碎的微粉碎可以利用在线磨机或珠磨机等湿式粉碎机进行。
本发明组合物作为水田用的除草剂,在灌水(日文:湛水)下的土壤处理和茎叶处理的任一处理方法中都可以使用。优选可以在采用茎叶处理的处理方法中使用。作为水田杂草,可举出例如,以千金子(chinese sprangletop、Leptochloa chinensis)、有芒千金子(bearded sprangletop、Leptochloa fascicularis)、稗(barnyard grass、Echinochloacrus-galli)、光头稗(junglerice、Echinochloa colonum)、水稗(late watergrass、Echinochloa oryzicola)、李氏禾(southern cutgrass、Leersia hexandra)、双穗雀稗(knotgrass、Paspalum distichum)、田间鸭嘴草(saramollagrass、Ischaemum rugosum)、筒轴茅(itchgrass、Rottboellia cochinchinensis)、宽叶臂形草(broadleafsignalgrass、Brachiaria platyphylla)、车前状臂形草(Alexandergrass、Brachiariaplantaginea)、马唐(large crabgrass、Digitaria sanguinalis)、龙爪茅(crowfootgrass、Dactyloctenium aegyptium)、牛筋草(goosegrass、Eleusine indica)、稻(redrice、Oryza sativa)、狗牙根(bermuda grass、Cynodon dactylon)、以及洋野黍(fallpanicum、Panicum dichotomiflorum)等为代表的禾本科(Gramineae)杂草、以黑慈姑(Eleocharis kuroguwai)、水虱草(globe fringerush、Fimbristylis miliacea)、萤蔺(japanese bulrush、Schoenoplectus juncoides)、三江蔗草(Schoenoplectusnipponicus)、水毛花(ricefield bulrush、Schoenoplectus mucronatus)、水莎草(Cyperus serotinus)、异型莎草(smallflower umbrella sedge、Cyperus difformis)、碎米莎草(rice flat sedge、Cyperus iria)、香附子(purple nutsedge、Cyperusrotundus)、油莎豆(yellow nutsedge、Cyperus esculentus)、以及海滨三棱草(cosmopolitan bulrush、Bolboschoenus martimus)等为代表的莎草科(Cyperaceae)杂草、以窄叶泽泻(water plantain、Alisma canaliculatum)、矮慈姑(pygmy arrowhead、Sagittaria pygmaea)、以及野慈姑(threeleaf arrowhead、Sagittaria trifolia)等为代表的泽泻科(Alismataceae)杂草、以疣草(asian spiderwort、Murdannia keisak)、以及饭包草(benghal dayflower、Commelina benghalensis)等为代表的鸭跖草科(Commelinaceae)杂草、以雨久花(heartleaf false pickerelweed、Monochoriakorsakowii)、鸭舌草(oval-leafed pondweed、Monochoria vaginalis)、沼生异蕊花(ducksalad、Heteranthera limosa)、以及凤眼蓝(water hyacinth、Eichhorniacrassipes)等为代表的雨久花科(Pontederiaceae)杂草、以三蕊沟繁缕(threestamenwaterwort、Elatine triandra)等为代表的沟繁缕科(Elatinaceae)杂草、以长叶水苋菜(redstem、Ammannia coccinea)、以及节节菜(indian toothcup、Rotala indica)等为代表的千屈菜科(Lythraceae)杂草、以假柳叶菜(Ludwigia epilobioides)、以及毛草龙(mexican primrose-willow、Ludwigia octovalvis)等为代表的柳叶菜科(Oenotheraceae)杂草、以虻眼(rushlike dopatrium、Dopatrium junceum)、白花水八角(Gratiola japonica)、石龙尾(dwarf ambulia、Limnophila sessiliflora)、陌上菜(prostrate false pimpernel、Lindernia pyxidaria)、以及北美母草(yellowseed falsepimpernel、Lindernia dubia)等为代表的玄参科(Scrophulariaceae)杂草、以喜旱莲子草(alligator weed、Alternanthera philoxeroides)、以及刺苋(spiny amaranth、Amaranthus spinosus)等为代表的苋科(Amaranthaceae)杂草、以水蓼(water pepper、Polygonum hydropiper)等为代表的蓼科(Polygonaceae)杂草、以尖瓣花(gooseweed、Sphenoclea zeylanica)等为代表的尖瓣花科(Sphenocleaceae)杂草、以合萌(indianjointvetch、Aeschynomene indica)、田菁(hemp sesbania、Sesbania exaltata)等为代表的豆科(Fabaceae)杂草、以大狼杷草(devil’s beggarticks、Bidens frondosa)、狼杷草(three-lobe beggarticks、Bidens tripartita)、鳢肠(false daisy、Ecliptaprostrata)、以及藿香蓟(goatweed、Ageratum conyzoides)等为代表的菊科(Asteraceae)杂草、以蕹菜(swamp morningglory、Ipomoea aquatica)等为代表的旋花科(Convolvulaceae)杂草、以南国田字草(water clover、Marsilea minuta)等为代表的苹科(Marsileaceae)杂草、以紫萍(common duckmeat、Spirodela polyrhiza)、以及稀脉浮萍(duckweed、Lemna paucicostata)等为代表的浮萍科(Lemnaceae)杂草、以及以眼子菜(roundleaf pondweed、Potamogeton distinctus)等为代表的眼子菜科(Potamogetonaceae)杂草等。
此外,本发明组合物作为旱田和果树园用的除草剂,在土壤处理、土壤混合处理和茎叶处理的任一处理方法中都可以使用。作为旱田杂草,可举出例如,以洋野黍(fallpanicum、Panicum dichotomiflorum)、野生高粱(shattercane、Sorgham bicolor)、石茅(johnson grass、Sorghum halepense)、稗(barnyard grass、Echinochloa crus-gallivar.crus-galli)、细叶旱稗(cockspur grass、Echinochloa crus-gallivar.praticola)、紫穗稗(japanese barnyard millet、Echinochloa utilis)、升马唐(southern crabgrass、Digitaria ciliaris)、两耳草(sourgrass、Digitariainsularis)、平枝马唐(jamaican crabgrass、Digitaria horizontalis)、野燕麦(wildoat、Avena fatua)、大穗看麦娘(blackgrass、Alopecurus myosuroides)、看麦娘(shortawn foxtail、Alopecurus aequalis)、阿披拉草(windgrass、Apera spica-venti)、旱雀麦(downy brome、Bromus tectorum)、多花黑麦草(italian ryegrass、Loliummultiflorum)、硬直黑麦草(rigid ryegrass、Lolium rigidum)、细虉草(littleseedcanarygrass、Phalaris minor)、早熟禾(annual bluegrass、Poa annua)、牛筋草(goosegrass、Eleusine indica)、狗尾草(green foxtail、Setaria viridis)、大狗尾草(giant foxtail、Setaria faberi)、信号草(signalgrass、Brachiaria decumbens)、以及蒺藜草(southern sandbur、Cenchrus echinatus)等为代表的禾本科(Poaceae)杂草、以香附子(purple nutsedge、Cyperus rotundus)等为代表的莎草科(Cyperaceae)杂草、以龙葵(black nightshade、Solanum nigrum)、以及曼陀罗(jimsonweed、Datura stramonium)等为代表的茄科(Solanaceae)杂草、以苘麻(velvetleaf、Abutilon theophrasti)、以及刺黄花稔(prickly sida、Sida spinosa)等为代表的锦葵科(Malvaceae)杂草、以圆叶牵牛(tall morning-glory、Ipomoea purpurea)、牵牛(ivyleaf morning-glory、Ipomoeahederacea)、以及打碗花(japanese bindweed、Calystegia hederacea)等为代表的旋花科(Convolvulaceae)杂草、以凹头苋(purple amaranth、Amaranthus lividus)、反枝苋(redroot pigweed、Amaranthus retroflexus)、长芒苋(palmer amaranth、Amaranthuspalmeri)、以及糙果苋(tall waterhemp、Amaranthus tuberculatus)等为代表的苋科(Amaranthaceae)杂草、以苍耳(common cocklebur、Xanthium strumarium)、豚草(commonragweed、Ambrosia artemisiifolia)、三裂叶豚草(giant ragweed、Ambrosia trifida)、加拿大飞蓬(horseweed、Conyza canadensis)、向日葵(common sunflower、Helianthusannuus)、同花母菊(pineappleweed、Matricaria matricarioides)、粗毛牛膝菊(hairygalinsoga、Galinsoga ciliata)、丝路蓟(canada thistle、Cirsium arvense)、欧洲千里光(common groundsel、Senecio vulgaris)、以及一年蓬(annual fleabane、Erigeronannuus)等为代表的菊科(Asteraceae)杂草、以蔊菜(variableleaf yellowcress、Rorippaindica)、野欧白芥(wild mustard、Sinapis arvensis)、以及荠(shepherd’s purse、Capsella bursa-pastoris)等为代表的十字花科(Brassicaceae)杂草、以长鬃蓼(oriental lady’s thumb、Persicaria longiseta)、以及卷茎蓼(wild buckwheat、Polygonum convolvulus)等为代表的蓼科(Polygonaceae)杂草、以马齿苋(commonpurslane、Portulaca oleracea)等为代表的马齿苋科(Portulacaceae)杂草、以藜(lambsquarters、Chenopodium album)、小藜(figleaved goosefoot、Chenopodiumficifolium)、地肤(kochia、Kochia scoparia)、以及刺沙蓬(russian thistle、Salsolatragus)等为代表的藜科(Chenopodiaceae)杂草、以繁缕(common chickweed、Stellariamedia)等为代表的石竹科(Caryophyllaceae)杂草、以阿拉伯婆婆纳(persian speedwell、Veronica persica)等为代表的车前科(Plantaginaceae)杂草、以鸭跖草(asiaticdayflower、Commelina communis)、以及饭包草(benghal dayflowe、Commelinabenghalensis)等为代表的鸭跖草科(Commelinaceae)杂草、以宝盖草(henbit、Lamiumamplexicaule)、以及紫花野芝麻(purple deadnettle、Lamium purpureum)等为代表的唇形科(Lamiaceae)杂草、以白苞猩猩草(wild poinsettia、Euphorbia heterophylla)、以及斑地锦(spotted spurge、Euphorbia maculata)等为代表的大戟科(Euphorbiaceae)杂草、以拉拉藤(false cleavers、Galium spurium)、以及东南茜草(asian madder、Rubiaakane)等为代表的茜草科(Rubiaceae)杂草、以三色堇(pansy、Viola tricolor)等为代表的堇菜科(Violaceae)杂草、以虞美人(filed poppy、Papaver rhoeas)等为代表的罂粟科(Papaveraceae)杂草、以田菁(hemp sesbania、Sesbania exaltata)、以及钝叶番泻(sicklepod、Cassia obtusifolia)等为代表的豆科(Fabaceae)杂草、以及以酢浆草(creeping woodsorrel、Oxalis corniculata)等为代表的酢浆草科(Oxalidaceae)杂草等。
进一步,本发明组合物例如可以将在堤坝的坡面、河川用地、道路的路肩和坡面、铁道用地、公园绿地、运动场、停车场、机场、工场和储存设备等的工业设施用地、休耕地、或市区的空闲地等需要控制杂草的生长的非农耕地、或果园地、牧场地、草坪地、林业地等产生的广范围的杂草除草。作为该杂草,除了在旱田和果树园用杂草中所说明的以外,还可举出早熟禾(annual bluegrass、Poa annua)、药用蒲公英(dandelion、Taraxacumofficinale)、香丝草(hairy fleabane、Conyza bonariensis)、加拿大飞蓬(horseweed、Conyza canadensis)、苏门白酒草(guernsey fleabane、Conyza sumatrensis)、弯曲碎米荠(wavy bittercress、Cardamine flexuosa)、白车轴草(white clover、Trifoliumrepens)、天胡荽(lawn pennywort、Hydrocotyle sibthorpioides)、车前(Chineseplantain、Plantago asiatica)、短叶水蜈蚣(green kyllinga、Kyllinga brevifolia)、问荆(field horsetail、Equisetum arvense)等。
本发明组合物通过对有用植物、或想要使有用植物生长或已经生长的场所、或非农耕地,同时或分开作用,从而可以控制对有用植物不期望的植物的生长。另外,上述所谓有用植物,包含旱田作物或水田作物、园艺作物、草、果树等。
另外,本发明中所谓有用植物,具体而言,可以举出例如,玉米、稻、小麦、大麦、黑麦、燕麦、高粱、棉、大豆、花生、荞麦、甜菜、菜籽、向日葵、甘蔗和烟草等农作物类;茄科蔬菜(茄子、番茄、甜椒、辣椒、马铃薯等)、葫芦科蔬菜(黄瓜、南瓜、西葫芦、西瓜、甜瓜等)、十字花科蔬菜(萝卜、芜菁、辣根、擘蓝、白菜、甘蓝、芥菜、绿花菜、花椰菜等)、菊科蔬菜(牛蒡、茼蒿、菜蓟、莴苣等)、百合科蔬菜(葱、洋葱、大蒜、石刁柏)、伞形科蔬菜(胡萝卜、荷兰芹、旱芹、欧防风等)、藜科蔬菜(菠菜、甜菜等)、唇形科蔬菜(紫苏、薄荷、罗勒等)、草莓、番薯、日本薯蓣和芋等蔬菜类;梨果类(苹果、西洋梨、日本梨、木瓜、榅桲等)、核果类(桃、李、油桃、梅、欧洲甜樱桃、杏、欧洲李等)、柑橘类(温州蜜柑、甜橙、柠檬、酸橙、葡萄柚等)、坚果类(栗子、核桃、榛子、扁桃、阿月浑子、腰果、澳洲坚果等)、浆果类(越橘、红莓苔子、黑莓、覆盆子等)、葡萄、柿、橄榄、枇杷、香蕉、咖啡、海枣、椰子和油棕等果实类;茶、桑、街道树(梣、桦树、大花四照花、桉、银杏、欧丁香、槭、橡、杨、紫荆、枫、悬铃木、榉树、日本香柏、日本冷杉、日本铁杉、杜松、松树、云杉、红豆杉、榆、七叶树等)、珊瑚树、罗汉松、日本柳杉、日本扁柏、变叶木、冬青卫矛和光叶石楠等除果树以外的树木类;结缕草类(结缕草、沟叶结缕草等)、狗牙根类(狗牙根等)、剪股颖类(巨序剪股颖、西伯利亚剪股颖、细弱剪股颖等)、早熟禾类(草地早熟禾、普通早熟禾等)、羊茅类(苇状羊茅、细羊茅、匍匐紫羊茅等)、黑麦草类(多花黑麦草、黑麦草等)、鸭茅和梯牧草等草坪类;油棕和麻风树等油粮作物类;花卉类(蔷薇、香石竹、菊、洋桔梗、缕丝花、火石花、万寿菊、鼠尾草、矮牵牛、马鞭草、郁金香、紫菀、龙胆、百合、三色堇、仙客来、兰、铃兰、薰衣草、紫罗兰、羽衣甘蓝、报春花、一品红、唐菖蒲、卡特兰、雏菊、马鞭草、蕙兰、秋海棠等);观叶植物等,但不限定于此。
本发明组合物可以通过例如用原液或水稀释为50~5000倍左右,使用喷雾机等散布于作物、树木或其生长的土壤的方法;用原液或水稀释为2~100倍左右,从空中使用直升机等进行散布的方法来施用。
本发明组合物在与包含化合物(1)的非晶体的组合物相比的情况下,例如组合物中的化合物(1)未固化等的保存稳定性、流动性、除草效果等优异。特别是在本发明组合物为悬浮状制剂、水性悬浮状制剂的情况下变得更显著。
实施例
以下通过以本发明结晶的制造例作为实施例而具体地说明,从而进一步详细地说明本发明,但本发明不限定于此。
另外,各种测定条件如下所述。
[粉末X射线衍射测定条件]
装置:X’PERT-PRO MPD(スペクトリス株式会社制)
测定法:透射法
X射线:Cu-Kα
电压:45kV
电流:40mA
取样间隔:0.0070deg
数据范围:2θ=5~40deg
[差示扫描量热测定条件]
装置:DSC-60(株式会社岛津制作所制)
升温:20℃-(10℃/min)-450℃
气氛:氮气
对照:Al2O3
容器:SUS制
取样:1秒
[制造例1]:本发明结晶的制造其1
在3-[(异丙基磺酰基)甲基]-5-(三氟甲基)-[1,2,4]三唑并[4,3-a]吡啶-8-甲酸34.83g和1,2-二氯乙烷348.30g的混合溶液中,在加热回流下添加亚硫酰氯14.90g。在添加结束后,将该反应混合物在加热回流下搅拌4.5小时。在搅拌结束后,在减压下,在60℃下将溶剂80.62g蒸馏除去。在蒸馏除去结束后,在60℃下添加5-甲基-1,3,4-二唑-2-胺9.83g和1,2-二氯乙烷174.20g。在添加结束后,在减压下,在60℃下将该反应混合物的溶剂179.00g蒸馏除去。在蒸馏除去结束后,在60℃下添加1,2-二氯乙烷175.00g、乙酸钾2.51g和水175.00g,进行分液。将所得的水层利用1,2-二氯乙烷175.00g进行提取。将所得的有机层水洗后,在减压下,在70℃下将溶剂307.45g蒸馏除去。在蒸馏除去结束后,在所得的浆料中,在70℃下添加1,4-二烷209.00g。在添加结束后,将所得的浆料以1小时25℃的冷却速度冷却直到-2℃,在该温度下搅拌1小时后,进行了过滤。将所得的结晶在0℃下用乙酸乙酯105.00g洗涤后,在减压下干燥,从而获得了目标物质的结晶31.40g。
测定了所得的结晶的粉末X射线衍射,结果显示图1的衍射图案。
此外,实施了所得的结晶的差示扫描量热测定,结果显示图2的峰图案。
[制造例2]:本发明结晶的制造其2
在3-[(异丙基磺酰基)甲基]-5-(三氟甲基)-[1,2,4]三唑并[4,3-a]吡啶-8-甲酸9.93g和1,2-二氯乙烷99.3g的混合溶液中,在加热回流下添加亚硫酰氯4.10g。在添加结束后,将该反应混合物在加热回流下搅拌4小时。在搅拌结束后,在减压下,在60℃下将溶剂20.5g蒸馏除去。在蒸馏除去结束后,在60℃下添加5-甲基-1,3,4-二唑-2-胺2.80g和1,2-二氯乙烷49.7g。在添加结束后,在减压下,在60℃下将该反应混合物的溶剂66.5g蒸馏除去。在蒸馏除去结束后,在60℃下添加1,2-二氯乙烷66.5g。在添加结束后,在减压下,在60℃下将该反应混合物的溶剂56.6g蒸馏除去。在蒸馏除去结束后,在60℃下添加1,2-二氯乙烷56.6g、乙酸钾0.69g和水44.7g,进行分液。将所得的水层利用1,2-二氯乙烷39.7g进行提取。将所得的有机层水洗后,在减压下,在60℃下将溶剂69.5g蒸馏除去。在蒸馏除去结束后,在所得的浆料中,在60℃下添加N,N-二甲基甲酰胺9.93g。在添加结束后,将该混合溶液在85℃下搅拌而使结晶溶解。将该混合溶液冷却到60℃,在搅拌中添加目标物质的晶种(使用了在制造例1中获得的目标物质的结晶)5mg。在添加结束后,在60℃下继续搅拌,通过目视确认了结晶的析出后,以1小时30℃的冷却速度冷却直到-2℃。将所得的浆料在-2℃下搅拌3小时后,进行了过滤。将所得的结晶在0℃下用1,2-二氯乙烷9.93g洗涤后,在减压下干燥,从而获得了目标物质的结晶9.51g。
测定了所得的结晶的粉末X射线衍射,结果显示图1的衍射图案。
此外,实施了所得的结晶的差示扫描量热测定,结果显示图2的峰图案。
[制造例3]:本发明结晶的制造其3
工序1:3-[(异丙基磺酰基)甲基]-5-(三氟甲基)-[1,2,4]三唑并[4,3-a]吡啶-8-甲酰氯的合成
在3-[(异丙基磺酰基)甲基]-5-(三氟甲基)-[1,2,4]三唑并[4,3-a]吡啶-8-甲酸1.00g和甲苯10g的混合溶液中,在加热回流下添加亚硫酰氯0.43g。在添加结束后,将该反应混合物在加热回流下搅拌1小时。在搅拌结束后,在减压下将溶剂蒸馏除去,从而以浅褐色固体的形式获得了目标物质1.10g。
熔点:140~142℃
工序2:本发明结晶的制造
在3-[(异丙基磺酰基)甲基]-5-(三氟甲基)-[1,2,4]三唑并[4,3-a]吡啶-8-甲酰氯1.10g和甲苯10g的混合溶液中,在室温下添加5-甲基-1,3,4-二唑-2-胺0.285g。在添加结束后,将该反应混合物在加热回流下搅拌2小时。在搅拌结束后,将该反应混合物冷却直到室温。将所得的浆料在室温下搅拌1小时后,进行了过滤。将所得的结晶在室温下用甲苯5.0g洗涤后,在减压下干燥,从而获得了目标物质的结晶1.00g。
测定了所得的结晶的粉末X射线衍射,结果显示图1的衍射图案。
[制造例4]:本发明结晶的制造其4
工序1:3-[(异丙基磺酰基)甲基]-5-(三氟甲基)-[1,2,4]三唑并[4,3-a]吡啶-8-甲酰氯的合成
在3-[(异丙基磺酰基)甲基]-5-(三氟甲基)-[1,2,4]三唑并[4,3-a]吡啶-8-甲酸1.00g和1,2-二氯乙烷10g的混合溶液中,在加热回流下添加亚硫酰氯0.43g。在添加结束后,将该反应混合物在加热回流下搅拌4小时。在搅拌结束后,在减压下将溶剂蒸馏除去,从而以浅褐色固体的形式获得了目标物质1.08g。
工序2:本发明结晶的制造
在3-[(异丙基磺酰基)甲基]-5-(三氟甲基)-[1,2,4]三唑并[4,3-a]吡啶-8-甲酰氯1.08g和1,2-二氯乙烷10g的混合溶液中,在室温下添加5-甲基-1,3,4-二唑-2-胺0.285g。在添加结束后,将该反应混合物在加热回流下搅拌3小时。在搅拌结束后,将该反应混合物冷却直到室温。将所得的浆料在室温下搅拌1小时后,进行了过滤。将所得的结晶在室温下用1,2-二氯乙烷3.0g洗涤后,在减压下干燥,从而获得了目标物质的结晶0.484g。
测定了所得的结晶的粉末X射线衍射,结果显示图1的衍射图案。
[参考例1]:化合物(1)的非晶体的制造按照国际公开第2014/192936号的实施例中的合成例2的记载实施了制造。
在3-[(异丙基磺酰基)甲基]-5-(三氟甲基)-[1,2,4]三唑并[4,3-a]吡啶-8-甲酸200mg、5-甲基-1,3,4-二唑-2-胺67.8mg和N,N-二甲基甲酰胺5ml的混合溶液中,在室温下添加1-乙基-3-(3-二甲基氨基丙基)碳二亚胺盐酸盐131.1mg和1-羟基-7-氮杂苯并三唑93.2mg。在添加结束后,将该反应混合物在室温下搅拌24小时。在搅拌结束后,添加水使反应停止后,利用氯仿进行了提取(10ml×1次)。在将所得的有机层水洗后,用无水硫酸钠干燥,在减压下将溶剂蒸馏除去。将所得的残渣利用硅胶色谱{正己烷:乙酸乙酯:甲醇=50:50:0~0:100:0~0:80:20(体积比)}精制,获得了化合物(1)的非晶体204.4mg。
测定了所得的非晶体的粉末X射线衍射,结果显示图3的衍射图案。
此外,实施了所得的非晶体的差示扫描量热测定,结果显示图4的峰图案。
产业可利用性
根据本发明,能够制造化合物(1)的结晶。
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