CN114853647B - 一种含硫醚(亚砜)取代的联苯类化合物及其应用 - Google Patents
一种含硫醚(亚砜)取代的联苯类化合物及其应用 Download PDFInfo
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- CN114853647B CN114853647B CN202210098352.XA CN202210098352A CN114853647B CN 114853647 B CN114853647 B CN 114853647B CN 202210098352 A CN202210098352 A CN 202210098352A CN 114853647 B CN114853647 B CN 114853647B
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- C07C323/01—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton
- C07C323/09—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton having sulfur atoms of thio groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
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- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/04—Sulfonic acids; Derivatives thereof
- A01N41/08—Sulfonic acid halides; alpha-Hydroxy-sulfonic acids; Amino-sulfonic acids; Thiosulfonic acids; Derivatives thereof
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- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
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Abstract
本发明属农用杀虫杀螨剂领域。具体地涉及一种含硫醚(亚砜)取代的联苯类化合物及其应用。结构如通式I所示:
Description
技术领域
本发明属农用杀虫杀螨剂领域,具体地涉及一种含硫醚(亚砜)取代的联苯类化合物及其应用。
背景技术
专利CN105541682A中公开了如下通式化合物及具体化合物KC1(化合物编号1)、KC2(化合物编号2)和KC3(化合物编号3),具有一定的杀螨活性:
现有技术中如本发明通式I所示的化合物及其杀虫杀螨活性未见报道。并且,同现有技术相比,本发明化合物具有更高的杀虫及杀螨活性。
发明内容
本发明的目的在于提供一种杀虫杀螨效果更好的含硫醚(亚砜)取代的联苯类化合物,它可应用于农业、林业及卫生领域中防治害虫害螨。
本发明的技术方案如下:
一种含硫醚(亚砜)取代的联苯类化合物,如通式I所示:
通式I中:
R1选自氢或卤素;
R2、R3各自独立地选自氢、氰基、环丙基、C1-C3烷基或卤代C1-C3烷基;
m、n各自独立地选自0或1。
在一种可能的实现方式中,通式I中,
R1选自氢、氟、氯或溴;
R2、R3各自独立地选自氢、氰基、环丙基、甲基、乙基、正丙基、异丙基、-CF3、-CHF2、-CH2F、-CH2CF3、-CH2CHF2或-CH2CH2F;
m、n各自独立地选自0或1。
在一种可能的实现方式中,通式I中,
R1选自氟;
R2、R3各自独立地选自氢、氰基、环丙基、甲基、乙基、正丙基、异丙基、-CF3、-CHF2、-CH2F、-CH2CF3、-CH2CHF2或-CH2CH2F;
m、n各自独立地选自0或1。
在一种可能的实现方式中,通式I中,
R1选自氟;
R2、R3选自-CF3;
m、n各自独立地选自0或1。
一种用于制备上述含硫醚(亚砜)取代的联苯类化合物的中间体化合物,所述中间体化合物如通式II所示:
通式II中:
R1选自氢或卤素。
一种用于制备上述含硫醚(亚砜)取代的联苯类化合物的中间体化合物,所述中间体化合物如通式III所示:
通式III中:
R1选自氢或卤素。
一种用于制备上述通式II化合物或通式III化合物的中间体化合物,所述中间体化合物如通式IV所示:
通式IV中:
R1选自氢或卤素。
上述通式I化合物、通式II化合物、通式III化合物及通式IV化合物的定义中,卤素是指氟、氯、溴或碘;烷基是指直链或支链烷基,例如甲基、乙基、正丙基、异丙基或不同的丁基异构体;卤代烷基是指直链或支链烷基,在这些烷基上的氢原子可部分或全部被卤素所取代,例如-CF3、-CHF2、-CH2F、-CH2CF3、-CH2CHF2或-CH2CH2F等。
本发明部分通式I化合物如表1~表10所示,但本发明绝非仅限于这些化合物。
表1
通式I中,当R1 = F且R2 = R3时,R2或R3为不同的取代基以及m、n为不同的数值见表1,代表化合物编号为1.1-1.39。
表2:通式I中,当R1 = H且R2 = R3时,R2或R3为不同的取代基以及m、n为不同的数值与表1一致,代表化合物编号为2.1-2.39,依次对应表1的1.1-1.39。
表3:通式I中,当R1 = Cl且R2 = R3时,R2或R3为不同的取代基以及m、n为不同的数值与表1一致,代表化合物编号为3.1-3.39,依次对应表1的1.1-1.39。
表4:通式I中,当R1 = Br且R2 = R3时,R2或R3为不同的取代基以及m、n为不同的数值与表1一致,代表化合物编号为4.1-4.39,依次对应表1的1.1-1.39。
表5:通式I中,当R1 = I且R2 = R3时,R2或R3为不同的取代基以及m、n为不同的数值与表1一致,代表化合物编号为5.1-5.39,依次对应表1的1.1-1.39。
通式I中,当R1 = F,R2= -CF3时,R3为不同的取代基以及m、n为不同的数值见表6,代表化合物编号为6.1-6.36。
表6
表7:通式I中,当R1 = H,R2= -CF3时,R3为不同的取代基以及m、n为不同的数值与表1一致,代表化合物编号为7.1-7.36,依次对应表6的6.1-6.36。
表8:通式I中,当R1 = Cl,R2= -CF3时,R3为不同的取代基以及m、n为不同的数值与表1一致,代表化合物编号为8.1-8.36,依次对应表6的6.1-6.36。
表9:通式I中,当R1 = Br,R2= -CF3时,R3为不同的取代基以及m、n为不同的数值与表1一致,代表化合物编号为9.1-9.36,依次对应表6的6.1-6.36。
表10:通式I中,当R1 = I,R2= -CF3时,R3为不同的取代基以及m、n为不同的数值与表1一致,代表化合物编号为10.1-10.36,依次对应表6的6.1-6.36。
本发明部分通式II化合物如表11所示,但本发明绝非仅限于这些化合物。
表11
。
本发明部分通式III化合物如表12所示,但本发明绝非仅限于这些化合物。
表12
。
本发明部分通式IV化合物如表13所示,但本发明绝非仅限于这些化合物。
表13
。
本发明的通式I化合物、通式II化合物、通式III化合物及通式IV化合物可按照以下方案制备,除另有注明外,式中各基团的定义同前。
方案一:用于制备m=n=0的通式I化合物及通式II化合物、通式III化合物以及通式IV化合物:
通式VII化合物与亚硝酸钠、一种或多种酸、碘化钾反应可制得通式VI化合物。酸可以是无机酸或有机酸,例如盐酸、氢溴酸、硫酸、磷酸、甲酸、乙酸、丙酸、丁酸、戊酸、三氟乙酸、草酸、丙二酸或甲磺酸等。反应溶剂可为水、氯仿、二氯甲烷、四氯化碳、己烷、苯、甲苯、乙酸乙酯、DMF、四氢呋喃或二氧六环等。反应通常在0-100°C的温度下进行。反应时间通常在0.5-48小时。
通式VII化合物可通过购买获得。
通式VI化合物与联硼酸频哪醇酯在适宜的溶剂中、适宜的碱、适宜的钯催化剂存在下,温度从-10℃到溶剂沸点下反应0.5-48小时可制得通式V化合物。适宜的溶剂可选自水、二氯甲烷、氯仿、四氯化碳、己烷、苯、甲苯、乙腈、四氢呋喃、1, 4二氧六环、DMF或DMSO等。适宜的碱包括碱金属如锂、钠或钾的氢化物如氢化钠、氢化钾,碱金属如锂、钠或钾的氢氧化物如氢氧化钠、氢氧化钾,还可以是碱金属锂、钠、钾或铯的碳酸盐如碳酸钠、碳酸铯,也可以是有机碱如三乙胺、叔丁醇钠或叔丁醇钾等。适宜的钯催化剂可为四(三苯基膦)钯、[1, 1’-双(二苯基膦基)二茂铁]二氯化钯等。某些情况下,还可以加入适宜的配体如1,1’-双(二苯基膦基)二茂铁、三苯基膦、三叔丁基膦等。
通式V化合物与磺化试剂反应可制得通式IV化合物。反应通常在0-200℃(例如190℃、170℃、150℃、130℃、110℃、100℃、90℃、80℃、70℃、60℃、50℃、30℃)的温度下进行。反应时间通常在0.5-48小时。磺化试剂可为氯磺酸、发烟硫酸、浓硫酸、三氧化硫或一氯化硫等。通式V化合物与磺化试剂的加料摩尔比为1:1-100(例如1:1-90、1:1-80、1:1-70、1:1-60、1:1-50、1:1-40、1:1-30、1:1-20、1:1-10、1:1-8、1:1-6、1:1-4、1:1-3、1:1-2)。
通式IV化合物与还原试剂反应可制得通式II化合物或通式III化合物。反应通常在在0-150℃(例如140℃、130℃、120℃、110℃、100℃、90℃、80℃、70℃、60℃、50℃、30℃)下进行。反应时间通常在0.5-48小时。还原试剂可为红磷、锌、铁、铜、镍或者红磷、锌、铁、铜、镍以任意比例混合的混合物;通式IV化合物与还原试剂的加料摩尔比为1:1-30(例如1:1-25、1:1-20、1:1-10、1:1-9、1:1-8、1:1-7、1:1-6、1:1-5、1:1-4、1:1-3、1:1-2)。反应可加入适量的甲酸、乙酸、三氟乙酸、盐酸、硫酸或硝酸等有机酸或无机酸;通式IV化合物与酸的加料摩尔比为1:1-100(例如1:1-90、1:1-80、1:1-70、1:1-60、1:1-50、1:1-40、1:1-30、1:1-20、1:1-10、1:1-9、1:1-8、1:1-7、1:1-6、1:1-5、1:1-4、1:1-3、1:1-2)。
通式III化合物经常规酸性水解或碱性水解可制得通式II化合物。
通式II化合物或通式III化合物与卤代试剂或磺酸酯在适宜的溶剂中、适宜的碱存在下,可制得通式I-1化合物。卤代试剂可为三氟碘乙烷、碘甲烷或碘乙烷等,磺酸酯可为甲磺酸2, 2, 2-三氟乙酯、苯磺酸2, 2, 2-三氟乙酯或2, 2, 2-三氟对甲苯磺酸乙酯等;通式II化合物或通式III化合物与卤代试剂的加料摩尔比为1:1-100(例如1:1-90、1:1-80、1:1-70、1:1-60、1:1-50、1:1-40、1:1-30、1:1-20、1:1-10、1:1-9、1:1-8、1:1-7、1:1-6、1:1-5、1:1-4、1:1-3、1:1-2)。适宜的碱可相同或不同的为三甲胺、三乙胺、吡啶、DBU、4-二甲氨基吡啶、N, N-二异丙基乙胺等有机碱,氢化钠、氢化钾等碱金属氢化物,氢氧化钠、氢氧化钾等碱金属氢氧化物,氢氧化钙等碱土类金属氢氧化物,碳酸钠、碳酸钾等碱金属碳酸盐,碳酸氢钠等碱金属碳酸氢盐,甲醇钠、乙醇钠、乙醇钾、叔丁醇钾、叔丁醇钠等金属醇盐;通式II化合物或通式III化合物与碱的加料摩尔比为1:1-20(例如1:1-18、1:1-16、1:1-14、1:1-12、1:1-10、1:1-9、1:1-8、1:1-7、1:1-6、1:1-5、1:1-4、1:1-3、1:1-2)。适宜的溶剂可相同或不同的为苯、甲苯、二甲苯等芳烃类,丙酮、甲乙酮、甲基异丁基酮等酮类,氯仿、二氯甲烷等卤代烃类,乙酸甲酯、乙酸乙酯等酯类,四氢呋喃、二噁烷、二乙醚、1, 2-二甲氧基乙烷、1, 4-二氧六环等醚类,水、乙腈、N, N-二甲基甲酰胺、N-甲基吡咯烷酮、二甲基亚砜等极性溶剂类或上述溶剂的混合溶剂。反应通常在0℃到溶剂沸点下进行。反应时间通常在0.5-48小时。
方案二:用于制备m=1或n=1及m=n=1的通式I化合物:
通式I-1化合物与氧化试剂反应可制得通式I-2化合物,通式I-2化合物与氧化试剂进一步反应可制得通式I-4化合物;同样地,通式I-1化合物与氧化试剂反应可制得通式I-3化合物,通式I-3化合物与氧化试剂进一步反应可制得通式I-4化合物。氧化试剂可为间氯过氧苯甲酸、双氧水或(偏)高碘酸钠等。反应溶剂可为水、甲醇、乙醇、乙醚、二氯甲烷、氯仿、四氯化碳、己烷、苯、甲苯、乙酸乙酯、DMF、四氢呋喃或二氧六环等。反应通常在0-100℃的温度下进行,优选在0-30℃进行。反应时间通常在10分钟-48小时。
本发明的通式I化合物展现出有效的杀虫效果。因此,本发明的通式I化合物可以用作杀虫剂。本发明的通式I化合物也对有毒的害虫展现出合适的防治效果,且对栽培的作物植物没有植物毒性。此外,本发明的化合物可用于防治多种害虫,例如有害的刺吸式昆虫、咀嚼式昆虫以及其他植物寄生害虫、储存谷物害虫、卫生害虫等,并且可用于消毒和杀灭它们。
这些有害的昆虫可举例说明如下:
作为昆虫,
甲虫(鞘翅目昆虫(Coleopteran)),例如绿豆象(Callosobruchus Chinensis)、玉米象(Sitophilus zeamais)、赤拟谷盗(Tribolium Castaneum)、马铃薯瓢虫(Epilachnavigintioctomaculata)、细胸叩甲(Agriotes ogurae fuscicollis)、多色异丽金龟(Anomala rufocuprea)、马铃薯叶甲(Leptinotarsa decemlineata)、叶甲属(Diabroticaspp.)、松墨天牛(Monochamus alternatus endai)、稻根象(Lissorhoptrusoryzophilus)、褐粉蠹(Lyctus bruneus);
鳞翅目(lepidopteran)害虫,例如,舞毒蛾(Lymantria dispar)、黄褐天幕毛虫(Malacosoma neustria)、菜粉蝶日本亚种(Pieris rapae crucivora)、斜纹夜蛾(Spodoptera litura)、甘蓝夜蛾(Mamestra brassicae)、二化螟(Chilo suppressalis)、欧洲玉米螟(Ostrinia nubilalis)、干果斑螟(Cadra cautella)、chyanokokakumonhamaki(Adoxophyes honmai)、苹果小卷蛾(Cydia pomonella)、黄地老虎(Agrotis segetum)、大蜡螟(Galleria mellonella)、菜蛾(Plutella xylostella)、烟芽夜蛾(Heliothisvirescens)、桔潜蛾(Phyllocnistis citrella);
半翅目(Hemipterous)害虫,例如,黑尾叶蝉(Nephotettix cincticeps)、褐飞虱(Nilaparvata lugens)、康氏粉蚧(Pseudococcus comstocki)、矢尖盾蚧(Unaspisyanonensis)、桃蚜(Myzus persicas)、苹果蚜(Aphis pomi)、棉蚜(Aphis gossypii)、萝卜蚜(Lipaphis erysimi)、梨冠网蝽(Stephanitis nashi)、绿椿属(Nezara spp.)、温室粉虱(Trialeurodes vaporariorum)、Pshylla spp.;
缨翅目(Thysanoptera)害虫,例如棕榈蓟马(Thrips palmi)、西方花蓟马(Franklinella occidentalis);
直翅目(orthopteran)害虫,例如非洲蝼蛄(Gryllotalpa Africana)、非洲飞蝗(Locusta migratoria);
蜚蠊目(blattarian)害虫,例如德国蠊(Blattella germanica)、美洲大蠊(Periplaneta americana)、黄胸散白蚁(Reticulitermes speratus)、家白蚁(Coptotermes formosanus);
双翅目(Dipterous)害虫,例如家蝇(Musca domestica)、埃及伊蚊(Aedesaegypti)、灰地种蝇(Delia platura)、淡色库蚊(Culex pipiens pallens)、中华按蚊(Anopheles sinensis)、三带喙库蚊(Culex tritaeniorhynchus)、三叶草斑潜蝇(Liriomyza trifolii)等。
此外,本发明还包括通式I化合物用于控制害螨的用途。尤其是,通式I化合物对下列科的重要品种有活性:叶螨科(二斑叶螨、朱砂叶螨、苹果全爪螨、柑橘全爪螨等)、瘿螨科、跗线螨科等。
此外,作为线虫,可以提及南方根结线虫(Meloidogyne incognita)、松材线虫(Bursaphelenchus xylophilus)、水稻干尖线虫(Aphelenchoides besseyi)、大豆异皮线虫(Heterodera glycines)、短体线虫属(Pratylenchus spp.)等。
在本发明中,对包括所有此类害虫在内的有害害虫具有杀虫效果的物质被称作杀虫剂。
当用作杀虫剂时,本发明的活性化合物可以常用制剂的形式制备。所述制剂形式可包括,例如,溶液剂、乳剂、可湿性粉剂、颗粒状可湿性粉剂、悬浮剂、粉剂(powder)、泡沫剂、膏剂、片剂、颗粒剂、气雾剂、经活性化合物浸渍的天然试剂、经活性化合物浸渍的合成试剂、微胶囊剂、种子包衣剂、装备有燃烧装置的制剂(所述燃烧装置可为烟筒和雾筒、罐和盘管等)以及ULV(冷雾剂、热雾剂)等。
这些制剂可用本身已知的方法制备。例如它们可通过将所述活性化合物与填充剂(即液体稀释剂或载体、液化气稀释剂或载体、固体稀释剂或载体)混合,以及任选地与表面活性剂(即乳化剂和/或分散剂和/或发泡剂)等混合而制备。
当使用水作为填充剂时,例如,可使用有机溶剂作为助溶剂。
所述液体稀释剂或载体可包括,例如,芳香烃(二甲苯、甲苯、烷基萘等)、氯代芳烃或氯代脂族烃(例如氯苯、氯乙烯、二氯甲烷等)、脂族烃(例如环己烷或石蜡(例如矿物油馏分))、醇(例如丁醇、乙二醇,及其醚或酯等)、酮(例如丙酮、甲基乙基酮、甲基异丁基酮、环己酮等)、强极性溶剂(例如二甲基甲酰胺、二甲亚砜)、水等。
所述液化气稀释剂或载体可包括在大气压力和温度下以气体形式存在的那些,例如,丙烷、氮气、二氧化碳,以及气溶胶喷射剂例如卤代烃。
固体稀释剂的实例可包括粉碎的天然矿物(例如高岭土、粘土、滑石、白垩、石英、绿坡缕石、蒙脱石或硅藻土等)以及粉碎的合成矿物(例如细分散的硅酸、氧化铝和硅酸盐等)等。
用于颗粒剂的固体载体的实例可包括粉碎并分级的岩石(例如方解石、大理石、浮石、海泡石和白云石)、合成的无机或有机粉末的颗粒、和有机材料(例如锯屑、椰壳、玉米穗轴和烟草茎等)的细小颗粒等。
乳化剂和/或发泡剂的实例可包括非离子及阴离子乳化剂[例如,聚氧乙烯脂肪酸酯、聚氧乙烯脂肪酸醇醚(如烷基芳基聚乙二醇醚)、烷基磺酸盐、烷基硫酸盐和芳基磺酸盐]以及白蛋白水解产物等。
分散剂包括木质素亚硫酸盐废液和甲基纤维素。
制剂(粉末剂、颗粒剂和乳剂)中也可使用粘合剂。粘合剂的实例可包括羧甲基纤维素、天然或合成的聚合物(例如阿拉伯树胶、聚乙烯醇和聚乙酸乙烯酯等)。
也可使用着色剂。着色剂的实例可包括无机颜料(例如氧化铁、氧化钛和普鲁士蓝等)、有机染料例如茜素染料、偶氮染料或金属酞菁染料;及微量元素,例如铁盐、锰盐、硼盐、铜盐、钴盐、钼盐或锌盐。
制剂可含有的上述活性组分的量为0.1至99重量%,优选地为0.5至90重量%。
本发明通式I化合物可作为与其他活性化合物(例如杀虫剂、毒饵剂、消毒剂、杀螨剂、杀线虫剂、杀真菌剂、生长调节剂、除草剂等)的混合物,以市售有用制剂的形式或者由其制剂制得的使用形式提供。所述杀虫剂可包括,例如,有机磷试剂、氨基甲酸盐试剂、羧酸盐试剂、氯化烃试剂、以及由微生物制得的杀虫物质等。
此外,本发明的通式I化合物可作为与一种增效剂的混合物存在。所述制剂和使用形式可包括商业上可用的那些。增效剂自身不必具有活性。更确切地,它是增强活性化合物活性的化合物。
所包括的市售可用形式的本发明通式I化合物的量可在宽范围内变化。
本发明的通式I化合物的实际使用浓度可,例如,在0.0000001至100重量%之间,优选在0.00001至1重量%之间。
本发明的通式I化合物可以根据适合于使用形式的任何常规方法使用。
当本发明的活性化合物用于抵抗卫生害虫和储藏害虫时,该化合物具有对于存在于石灰材料中的碱性物质而言有效的稳定性。此外,它在木材和土壤中展现出卓越的残留效率。
本发明的活性化合物具有低毒性,并且可以安全地用于温血动物。
应明确的是,在本发明的权利要求所限定的范围内,可进行各种变换和改动。
具体实施方式
以下具体实施例用来进一步说明本发明,但本发明绝非限于这些例子。(除另有注明外,所用原料均有市售)
合成实施例
按照上述记载的合成路线,采用不同的原料化合物,即可分别制备获得本发明通式I、通式II、通式III、通式IV所示化合物,进一步具体描述如下:
实施例1:化合物1.22的制备
(1)中间体4-氯-2-氟-1-碘苯(VI-1)的制备
称取4-氯-2-氟苯胺(VII-1) 5.00 g (34.35 mmol),加入200 mL水、35 mL浓盐酸,降温至0~5 ℃,搅拌30 min。向其中缓慢滴加亚硝酸钠2.40 g (34.79 mmol)的100 mL水溶液,在此过程中,维持反应温度不超过0~5 ℃。滴加完毕后,继续搅拌反应1 h。
向该重氮盐溶液中缓慢滴加碘化钾5.70 g (34.34 mmol)的100 mL水溶液,在此过程中,维持反应温度不超过0~5 ℃。滴加完毕后,撤去冰浴,室温下继续搅拌反应3 h。TLC监测反应完毕后,加入300 mL乙酸乙酯稀释,有机层依次用200 mL水、200 mL饱和食盐水洗涤,无水硫酸镁干燥、过滤、减压脱溶,残余物柱层析纯化后得5.70 g红褐色液体,即中间体VI-1。
(2)中间体4, 4'-二氯-2, 2'-二氟-1, 1'-联苯(V-1)的制备
称取中间体4-氯-2-氟-1-碘苯(VI-1) 5.00 g (19.54 mmol),联硼酸频哪醇酯7.44 g (29.31 mmol),碳酸铯12.74 g (39.08 mmol),[1, 1’-双(二苯基膦基)二茂铁]二氯化钯0.09 g (0.12 mmol),1, 1’-双(二苯基膦基)二茂铁0.06 g (0.10 mmol),加入100mL 1, 4-二氧六环,3 mL水,加热回流反应3 h。TLC监测反应完毕后,加入200 mL乙酸乙酯稀释,有机层依次用200 mL水、200 mL饱和食盐水洗涤,无水硫酸镁干燥、过滤、减压脱溶,残余物柱层析纯化后得2.00 g白色固体,即中间体V-1。
(3)中间体4, 4'-二氯-6, 6'-二氟-[1, 1'-联苯]-3, 3'-二磺酰二氯化物(III-1)的制备
向反应瓶中加入氯磺酸481.6 g (4.14 mol),冰水冷却至0~5 ℃;加入中间体4,4'-二氯-2, 2'-二氟-1, 1'-联苯(IV-1) 50 g (0.19 mol),在此过程中反应液温度不超过10 ℃。升温至25~30℃,保温反应3 h。TLC监测反应完毕后,将反应液缓慢倾入碎冰中,有固体析出,过滤;滤液用乙酸乙酯和水萃取,有机层经饱和食盐水洗涤、无水硫酸镁干燥、过滤、减压脱溶后,得到淡黄色固体,与滤饼合并,干燥后得56.0 g淡黄色固体,即中间体III-1。中间体III-1的核磁数据如下:
1H NMR (600 MHz, DMSO-d 6) δ 7.92 – 7.86 (m, 2H), 7.55 – 7.50 (m, 2H)。
(4)中间体4, 4'-二氯-6, 6'-二氟-[1, 1'-联苯]-3, 3'-二硫醇(II-1)的制备
向反应瓶中依次加入乙酸0.70 g (11.69 mmol)、中间体4, 4'-二氯-6, 6'-二氟-[1, 1'-联苯]-3, 3'-二磺酰二氯化物(IV-1) 0.39 g (0.86 mmol)、红磷0.16 g(5.16 mmol)、碘0.02 g (0.09 mmol)、乙酸酐0.35 g (3.44 mmol),升温至回流反应1 h。TLC监测反应完毕后,将反应液热过滤,母液浓缩,用100 mL乙酸乙酯和100 mL水萃取分层,有机层加入碳酸氢钠调节pH为6~7,有机层减压浓缩得到0.28 g黄色固体,即中间体III-1。
向反应瓶中加入0.28 g黄色固体(III-1)、10 mL四氢呋喃、甲醛次硫氢钠0.12 g(12.86 mmol),冰水浴冷却至0~5 ℃。滴加氢氧化钠水溶液(0.17 g溶于10 mL水中),滴加过程中,控制温度0~5℃。滴加完毕后,继续搅拌反应30 min。TLC监测反应完毕后,向反应混合物中加入20 mL水、20 mL乙酸乙酯,萃取分层,弃去有机相。向水相中滴加浓盐酸(0.44g,4.30 mmoL),滴加完毕后,继续搅拌30 min,不断有固体洗出;加入20 mL乙酸乙酯,萃取,有机相经无水硫酸镁干燥,减压下浓缩,得到白色固体0.17 g,即中间体II-1。
(5)化合物1.22的制备
向反应瓶中依次加入中间体4, 4'-二氯-6, 6'-二氟-[1, 1'-联苯]-3, 3'-二硫醇(II-1) 8.00 g (24.85 mmol),80 mL丙酮,碳酸钾11.48 g (54.67 mmol),甲醛次硫酸钠3.23 g (27.34 mmol),三氟碘乙烷11.48 g (54.67 mmol),将反应液升至50℃反应5 h。TLC监测反应完毕后,反应液浓缩,残余物柱层析纯化后得8.45 g白色固体,即目标化合物1.22。化合物1.22的核磁数据如下:
1H NMR (400 MHz, Chloroform-d) δ 7.65 – 7.61 (m, 2H), 7.36 – 7.32 (m,2H), 3.45 (q, 4H)。
实施例2:化合物1.23和1.24的制备
将0.30 g (0.62 mmol)化合物1.22溶于10 mL氯仿中,降温至0~5°C,加入0.12 g(0.70 mmol,85%纯度)间氯过氧苯甲酸,搅拌反应1 h。TLC监测反应完毕后,反应液依次用硫代硫酸钠水溶液和碳酸氢钠水溶液洗涤并用无水硫酸镁干燥、过滤、减压脱溶,残余物柱层析纯化后分别得到0.16 g化合物1.23(白色固体)和0.12 g化合物1.24(白色固体)。核磁数据如下:
化合物1.23:1H NMR (600 MHz, Chloroform-d) δ 7.98 (d, 1H), 7.68 (d,1H), 7.40 – 7.34 (m, 2H), 3.84 – 3.74 (m, 1H), 3.51 – 3.40 (m, 3H)。
化合物1.24:1H NMR (600 MHz, Chloroform-d) δ 8.05 – 8.00 (m, 2H), 7.41– 7.36 (m, 2H), 3.84 – 3.73 (m, 2H), 3.53 – 3.41 (m, 2H)。
参照以上实施例可以制备本发明通式I中其它化合物。
生物活性测定
实施例3:粘虫、小菜蛾的生物活性测定
用本发明化合物及对照化合物KC1、KC2、KC3对几种昆虫进行了杀虫活性测定实验。测定方法如下:
待测化合物用丙酮/甲醇(1:1)的混合溶剂溶解后,用含有0.1%(wt)吐温80的水稀释至所需的浓度。
以粘虫、小菜蛾为靶标,采用Airbrush喷雾法进行活性测定。
(1)杀粘虫的活性测定
测定方法:将玉米叶片剪成长2 cm的叶段,Airbrush喷雾处理的压力为10 psi(约合0.7 kg/cm2),每叶段正反面喷雾,喷液量为0.5 mL。阴干后每处理接入10头3龄幼虫,每处理3次重复。处理后放入25℃、相对湿度60~70%观察室内培养,药后3天后调查存活虫数,计算死亡率。
对粘虫的部分测试结果如下:
在500 mg/L剂量下,药后3天,化合物1.22、1.23、1.24对粘虫的致死率在90%以上,对照化合物KC1、KC2、KC3对粘虫的致死率均为0。
(2)杀小菜蛾的活性测定
测定方法:将甘蓝叶片用打孔器打成直径2 cm的叶碟,Airbrush喷雾处理的压力为10 psi(约合0.7 kg/cm2),每叶碟正反面喷雾,喷液量为0.5 mL。阴干后每处理接入10头3龄幼虫,每处理3次重复。处理后放入25℃、相对湿度60~70%观察室内培养,药后3天后调查存活虫数,计算死亡率。
对小菜蛾的部分测试结果如下:
在500 mg/L剂量下,药后3天,化合物1.22、1.23、1.24对小菜蛾的致死率在90%以上,对照化合物KC1、KC2、KC3对小菜蛾的致死率均为0。
实施例4:杀螨活性测定
用本发明化合物进行温室杀螨活性测定。测定的方法如下:
根据待测化合物的溶解性,用丙酮或二甲基亚砜溶解,并用0.1%的吐温80溶液配制所需浓度的待测溶液50 mL,丙酮或二甲基亚砜在溶液中的含量不超过10%。
取两片真叶菜豆苗,接种朱砂叶螨成螨并调查基数后,用手持喷雾器进行整株喷雾处理,每处理3次重复,处理后置于标准观察室,72小时后调查存活螨数,计算死亡率。
测试结果如下:
药液浓度为5 mg/L时,化合物1.22、1.23、1.24对朱砂叶螨的致死率在90%以上。
选取本发明化合物1.22、1.23、1.24与对照化合物进行朱砂叶螨杀螨活性平行比较试验(药后3天),测定方法同前所述;结果如表14所示:
表14 本发明化合物1.22、1.23、1.24及对照化合物对朱砂叶螨杀螨活性平行比较试验
通过本发明化合物1.22与对照化合物KC1的比较、本发明化合物1.23与对照化合物KC2的比较、本发明化合物1.24与对照化合物KC3的比较可知:本发明化合物相比现有技术而言,具有更高的杀螨活性。
本发明的发明人通过大量试验,在现有化合物分子骨架的基础上,通过将现有技术联苯结构上的甲基变为氯原子,从而获得了本发明通式I化合物。由实施例3和实施例4活性对比实验可知:相比现有技术而言,本发明化合物具有意想不到的更好的杀虫、杀螨活性。
在有机分子中,由于取代基的电负性、体积大小或空间构型的不同,整个分子在昆虫、螨虫和植物等生物体内的输导性能或与受体结合差异性会很大,表现出的生物活性差异也会很大,而分子的输导性能和与受体结合的合适性是不可预测的,需要大量的创造性劳动才能获知,因此,本发明具有实质性的特点和显著的进步。
Claims (10)
1.一种含硫醚(亚砜)取代的联苯类化合物,其特征在于:化合物如通式I所示:
通式I中:
R1选自卤素;
R2、R3各自独立地选自卤代C1-C3烷基;
m、n各自独立地选自0或1。
2.根据权利要求1所述的化合物,其特征在于:通式I中
R1选自氟、氯或溴;
R2、R3各自独立地选自-CF3、-CHF2、-CH2F、-CH2CF3、-CH2CHF2或-CH2CH2F;
m、n各自独立地选自0或1。
3.根据权利要求2所述的化合物,其特征在于:通式I中
R1选自氟;
R2、R3各自独立地选自-CF3、-CHF2、-CH2F、-CH2CF3、-CH2CHF2或-CH2CH2F;
m、n各自独立地选自0或1。
4.根据权利要求3所述的化合物,其特征在于:通式I中
R1选自氟;
R2、R3选自-CF3;
m、n各自独立地选自0或1。
5.一种化合物,所述化合物为制备如权利要求1-4中任一项所述含硫醚(亚砜)取代的联苯类化合物的中间体,其特征在于,所述化合物具有如下通式II所示结构:
通式II中:
R1选自卤素。
6.一种化合物,所述化合物为制备如权利要求1-4中任一项所述含硫醚(亚砜)取代的联苯类化合物的中间体,其特征在于,所述化合物具有如下通式III所示结构:
通式III中:
R1选自卤素。
7.一种化合物,所述化合物为制备如权利要求5或6所述化合物的中间体,其特征在于,所述化合物具有如下通式IV所示结构:
通式IV中:
R1选自卤素。
8.一种按照权利要求1-4中任一项所述的通式I化合物在农业、林业领域中用作杀虫剂或杀螨剂的用途。
9.一种杀虫杀螨组合物,其特征在于:组合物中含有权利要求1-4中任一项所述的通式I化合物和农业上可接受的载体,组合物中活性组分的重量百分含量为0.1-99%。
10.一种控制农业或林业害虫害螨的方法,其特征在于:将有效量的权利要求9所述的组合物施于需要控制的害虫害螨或其生长介质上。
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