專(zhuān)利名稱(chēng)：苯基磺酰脲，其制備方法及其用作除草劑和植物生長(zhǎng)調(diào)節(jié)劑的制作方法
已知一些苯基磺酰脲具有除草和調(diào)節(jié)植物生長(zhǎng)的性質(zhì)；參見(jiàn)US-A-4,786,314，US-A-4,927,453和WO89/10921?？墒窃谝恍┣闆r下上述苯基磺酰脲在應(yīng)用上存在一些缺點(diǎn)，例如殘效高或?qū)χ匾淖魑镞x擇性差。
現(xiàn)已發(fā)現(xiàn)在苯環(huán)上具有一定基團(tuán)的苯基磺酰脲可有效地用作除草劑或植物生長(zhǎng)調(diào)節(jié)劑。本發(fā)明涉及式(I)的化合物或其鹽， 其中R1為CO-Q-R8，R2和R3各自獨(dú)立的為H或(C1-C4)烷基，R4為H，未取代或被一或多個(gè)下組包括的基團(tuán)取代的(C1-C8)烷基，上述取代基團(tuán)由鹵素、(C1-C4)烷氧基、(C1-C4)烷硫基、(C1-C4)烷基亞磺?；?C1-C4)烷基磺?；?、[(C1-C4)烷氧基]羰基和CN組成，或?yàn)槲幢蝗〈虮灰恢炼鄠€(gè)鹵原子取代的(C3-C6)鏈烯基，或?yàn)槲幢蝗〈虮灰恢炼鄠€(gè)鹵原子取代的(C3-C6)鏈炔基，或?yàn)榱u基，(C1-C4)烷氧基，[(C1-C4)烷基]羰基或(C1-C4)烷基磺?；笕齻€(gè)基團(tuán)各自未被取代或在烷基部分被一至多個(gè)鹵原子或被(C1-C4)烷氧基或(C1-C4)烷硫基取代，或?yàn)楸交酋；渲斜交俏幢蝗〈騼?yōu)選被一至多個(gè)下述基團(tuán)取代，取代基由鹵素、CN、NO2、(C1-C4)烷基、(C1-C4)鹵代烷基和(C1-C4)烷氧基組成，和R5為(C1-C4)烷基磺酰基或(C3-C6)鏈烯基磺?；髢蓚€(gè)基團(tuán)各自未被取代或被一至多個(gè)鹵原子或被(C1-C4)烷氧基或(C1-C4)烷硫基取代的，或?yàn)楸交酋；虮交驶髢蓚€(gè)基團(tuán)的苯基各自未被取代或優(yōu)選被一或多個(gè)下述基團(tuán)取代，上述取代基由鹵素、CN、NO2、(C1-C4)烷基、(C1-C4)鹵代烷基和(C1-C4)烷氧基組成，或?yàn)閱?或二-[(C1-C4)烷基]氨基磺酰基或[(C1-C6)烷基]羰基，后三個(gè)基團(tuán)各自未被取代或被一或多個(gè)下述基團(tuán)取代，上述取代基由鹵素、(C1-C4)烷氧基、(C1-C4)烷硫基、(C1-C4)烷基亞磺?；?C1-C4)烷基磺?；?、[(C1-C4)烷基]羰基、[(C1-C4)烷氧基]羰基和CN組成，或?yàn)榧柞；?，?CO-CO-R’的基團(tuán)其中R’＝H，OH，(C1-C4)烷氧基或(C1-C4)烷基，或?yàn)閇(C3-C6)環(huán)烷基]羰基，[(C2-C6)鏈烯基]羰基或[(C2-C6)鏈炔基]羰基，后三個(gè)基團(tuán)各自未被取代或被一或多個(gè)鹵原子取代，或?yàn)橄率降幕鶊F(tuán) 或R4和R5一起為式(-CH2)mB-或-B1-(CH2)ml-B-的鏈，上述鏈?zhǔn)俏幢蝗〈虮灰粋€(gè)或多個(gè)，優(yōu)選直至四個(gè)(C1-C3)烷基取代和m為3或4或m1為2或3，和W為氧或硫原子(即O或S)，B和B1各自獨(dú)立為SO2或CO，Q為O，S或-NR13-，T為O或S，R6為H，(C1-C4)烷基，(C1-C4)烷氧基，[(C1-C4)烷基]羰基或[(C1-C4)烷氧基]羰基，后四個(gè)基團(tuán)各自未被取代或在烷基部分被一至多個(gè)鹵原子取代，或?yàn)辂u素，NO2或CN，R7為H或CH3，R8為H，(C1-C4)烷基，(C3-C4)鏈烯基或(C3-C4)鏈炔基，后三個(gè)基團(tuán)各自未被取代或被一或多個(gè)由鹵素、(C1-C4)烷氧基、(C1-C4)烷硫基、[(C1-C4)烷基]羰基和[(C1-C4)烷氧基]羰基組成的一組基團(tuán)取代，R9為(C1-C4)烷基，(C3-C4)鏈烯基或(C3-C4)鏈炔基，后三個(gè)基團(tuán)各自未被取代或被一或多個(gè)由鹵素、(C1-C4)烷氧基、(C1-C4)烷硫基、[(C1-C4)烷基]羰基和[(C1-C4)烷氧基]羰基組成的一組基團(tuán)取代，R10和R11各自獨(dú)立地為H，(C1-C4)烷基，(C3-C4)鏈烯基或(C3-C4)鏈炔基，后三個(gè)基團(tuán)各自未被取代或被一或多個(gè)由鹵素、(C1-C4)烷氧基、(C1-C4)烷硫基、[(C1-C4)烷基]羰基和[(C1-C4)烷氧基]羰基組成的一組基團(tuán)取代，R12基團(tuán)與氮原子一起為5或6元雜環(huán)，上述雜環(huán)在可能的氧化態(tài)中可含有一個(gè)其它N，O和S雜原子，且是未被取代或被(C1-C4)烷基或氧基取代，或被苯環(huán)稠和，R13為H，(C1-C4)烷基，(C3-C4)鏈烯基或(C3-C4)鏈炔基，后三個(gè)基團(tuán)各自未被取代或被一或多個(gè)由鹵素、(C1-C4)烷氧基、(C1-C4)烷硫基組成的一組基團(tuán)取代，A為下式的基團(tuán) X和Y基團(tuán)之一是氫，鹵素，(C1-C3)烷基或(C1-C3)烷氧基，后兩個(gè)基團(tuán)是未被取代或被鹵素單取代或多取代或被(C1-C3)烷氧基單取代，和X和Y基團(tuán)的另一個(gè)是氫，(C1-C3)烷基，(C1-C3)烷氧基或(C1-C3)烷硫基，后三個(gè)含有烷基的基團(tuán)是未被取代或被鹵原子單或多取代或被(C1-C3)烷氧基或(C1-C3)烷硫基單取代或二取代，或?yàn)槭絅R14R15的基團(tuán)，(C3-C6)環(huán)烷基，(C2-C4)鏈烯基，(C2-C4)鏈炔基，(C3-C4)鏈烯氧基，(C3-C4)鏈炔氧基，Z為CH或N，R14和R15各自彼此獨(dú)立地為H，(C1-C3)烷基，(C3-C4)鏈烯基，X1為CH3、OCH3、OC2H5或OCHF2，Y1為-O-或-CH2-X2為CH3、C2H5或CH2CF3Y2為OCH3、OC2H5、SCH3、SCH2CH3、CH3或C2H5，X3為CH3或OCH3，Y3為H或CH3，X4為CH3、OCH3、OC2H5、CH2OCH3或Cl，Y4為CH3、OCH3、OC2H5或Cl和Y5為CH3、C2H5、OCH3或Cl。在式(I)和下文中，烷基、烷氧基、鹵代烷基、烷基氨基和烷硫基以及相應(yīng)的不飽和和/或取代的基團(tuán)在碳架中各自可為直鏈和支鏈的基團(tuán)。單獨(dú)的烷基或作為如烷氧基、鹵代烷基等的組成的烷基是甲基、乙基、正或異丙基、正-、異-、叔-或2-丁基；鏈烯基或鏈炔基具有相應(yīng)于烷基可能的不飽和基團(tuán)的定義，如2-丙烯基、2-或3-丁烯基、2-丙炔基、2-或3-丁炔基。鹵素為氟、氯、溴或碘；鹵代烷基是被一或多個(gè)鹵原子取代的烷基；鹵代烷基的實(shí)例為CF3、CHF2和CH2CF3。取代苯基優(yōu)選為被一或多個(gè)，優(yōu)選1，2或3個(gè)下組基團(tuán)取代的苯基，上組取代基團(tuán)由鹵素，如F、Cl、Br和I，優(yōu)選F、Cl和Br，以及烷基、鹵代烷基、烷氧基、鹵代烷氧基、羥基、氨基、硝基、氰基、烷氧羰基、烷基羰基、甲酰基、氨基甲?；?、單-和二烷基氨基羰基、單-和二烷基氨基、烷基亞磺?；屯榛酋；M成，且對(duì)于含有碳原子的基團(tuán)，上述含有一至四個(gè)碳原子、特別1或2碳原子的基團(tuán)是優(yōu)選的。在此一般優(yōu)選的取代基為由鹵素，例如氟和氯、C1-C4-烷基、優(yōu)選甲基或乙基，C1-C4-鹵代烷基、優(yōu)選三氟甲基，C1-C4-烷氧基、優(yōu)選甲氧基或乙氧基，C1-C4-鹵代烷氧基，硝基和氰基組成的一組基團(tuán)。
在需要時(shí)可被苯稠和和含有氮原子(例如，在N(R12)2的情況下)的5-或6-元雜環(huán)可以是飽和，不飽和或雜芳基，例如借助氮原子連接并選自下組的基團(tuán)，上述基團(tuán)由吡咯烷基、哌啶基、吡唑基、嗎啉基、吲哚基、喹啉基、嘧啶基、三唑基、噁唑基、吡啶基、嘧啶基、噠嗪基、吡嗪基、噻唑基、噁唑基、吡咯基、咪唑基和苯并惡唑基。
本發(fā)明還涉及式(I)化合物的各種異構(gòu)體，及其混合物。如在式(I)未具體指明的含有一或多個(gè)不對(duì)稱(chēng)碳原子或雙鍵的式(I)化合物。式(I)包括通過(guò)具體空間構(gòu)型確定的所有可能的立體異構(gòu)體，如對(duì)映體、非對(duì)映體、E和Z異構(gòu)體，上述所有的異構(gòu)體都可通過(guò)常規(guī)方法從立體異構(gòu)體的混合物或通過(guò)立體選擇性反應(yīng)結(jié)合應(yīng)用立體化學(xué)純的起始物而制備。
式(I)化合物可形成鹽，其中-SO2-NH-基的氫原子被適于農(nóng)用的陽(yáng)離子置換。例如上述鹽是金屬鹽、特別是堿金屬鹽或堿土金屬鹽、特別是鈉和鉀鹽、或銨鹽或與有機(jī)胺形成的鹽。
特別令人感興趣的是根據(jù)本發(fā)明的式(I)化合物或其鹽其中R4為H，未取代或被一或多個(gè)下組包括的基團(tuán)取代的(C1-C4)烷基，上述取代基團(tuán)由鹵素、(C1-C4)烷氧基、(C1-C4)烷硫基、(C1-C4)烷基磺?；(C1-C4)烷氧基]羰基和CN組成，或?yàn)?C3-C4)鏈烯基、(C3-C4)鏈炔基、羥基，(C1-C4)烷氧基，[(C1-C4)烷基]羰基或(C1-C4)烷基磺?；?，后五個(gè)基團(tuán)各自未被取代或在烷基部分被一至多個(gè)鹵原子取代，或?yàn)楸交酋；?，其中苯基是未被取代或被一或多個(gè)下述基團(tuán)取代的，取代基由鹵素、(C1-C4)烷基和(C1-C4)烷氧基組成，和R5為(C1-C4)烷基磺酰基、(C1-C4)鹵代烷基磺?；?、苯基磺?；虮交驶髢蓚€(gè)基團(tuán)中的苯基各自未被取代或被一至多個(gè)選自鹵原子、(C1-C4)烷基和(C1-C4)烷氧基的基團(tuán)取代，或?yàn)閱?或二-[(C1-C4)烷基]氨基磺?；?，未被取代或被一或多個(gè)鹵原子或(C1-C4)烷氧基或(C1-C4)烷硫基取代的[(C1-C6)烷基]羰基，或?yàn)榧柞；?、OHC-CO-、2-氧-(C3-C5)鏈烷?；?、[(C1-C4)烷氧基]草酰基、[(C3-C6)環(huán)烷基]羰基，[(C2-C4)鏈烯基]羰基或[(C2-C4)鏈炔基]羰基、或?yàn)橄率降幕鶊F(tuán) W為O或SR6為H、(C1-C4)烷基、(C1-C4)鹵代烷基、(C1-C4)烷氧基、(C1-C4)鹵代烷氧基或鹵素，R8各自為未被取代或被一或多個(gè)鹵原子取代的(C1-C4)烷基，或?yàn)?C3-C4)鏈烯基或(C3-C4)鏈炔基，R9為H、未被取代或被一或多個(gè)鹵原子或被(C1-C4)烷氧基、(C1-C4)烷硫基、[(C1-C4)烷氧基]羰基和[(C1-C4)烷基]羰基取代的(C1-C4)烷基，R10和R11各自獨(dú)立地為H、未被取代或被一或多個(gè)鹵原子取代的(C1-C4)烷基、或?yàn)?C3-C4)鏈烯基或(C3-C4)鏈炔基、其中R10和R11至少一個(gè)不是氫，R12基團(tuán)與氮原子一起為5或6元雜環(huán)，上述雜環(huán)在不同的氧化態(tài)中可含有一個(gè)其它N，O和S雜原子，且是未被取代或被(C1-C4)烷基或氧基取代，R13為H，未被取代或被一或多個(gè)由鹵素原子取代的(C1-C4)烷基、或?yàn)?C3-C4)鏈烯基或(C3-C4)鏈炔基。
優(yōu)選的式(I)化合物及其鹽是其中W為氧原子和A為下式的基團(tuán)的式(I)化合物 其中X、Y和Z如上述定義。特別優(yōu)選的式(I)化合物或其鹽，其中R4為H、(C1-C4)烷基、羥基或(C1-C4)烷氧基，R5為(C1-C4)烷基磺?；HO、未被取代或被一或多個(gè)鹵原子取代的[(C1-C4)烷基]羰基、或?yàn)閇(C1-C4)烷氧基]草?；(C3-C6)環(huán)烷基]羰基或下式的基團(tuán) 其中W，T和R9至R12如上面式(I)中的定義，R6為H、(C1-C3)烷基、(C1-C3)烷氧基或鹵素，A為下式的基團(tuán) Z為CH或N，優(yōu)選為CH，和X和Y基團(tuán)之一為鹵素、(C1-C2)烷基、(C1-C2)烷氧基、OCF2H、CF3或OCH2CF3和X和Y的另一個(gè)為(C1-C2)烷基、(C1-C2)烷氧基或(C1-C2)鹵代烷氧基。
鑒于便于制備或具有較好的生物活性的原因，其中基團(tuán)-CR2R3-NR4R5相對(duì)于R1基團(tuán)為鄰位或?qū)ξ换蛳鄬?duì)于磺基為鄰位的根據(jù)本發(fā)明的式(II)化合物及其鹽是特別令人感興趣的；-CR2R3-NR4R5基優(yōu)選的位置是R1基的對(duì)位。
本發(fā)明還涉及制備式(I)化合物及其鹽的方法，其中包括a)式(II)的化合物與式(III)雜環(huán)氨基甲酸酯反應(yīng) R*-O-CO-NR7-A(III)其中R*是必要時(shí)被取代的苯基或(C1-C4)烷基，或b)式(IV)的苯基磺?；被姿狨ヅc式(V)的氨基雜環(huán)反應(yīng) H-NR7-A(V)或c)式(VI)的磺酰基異氰酸酯與式(V)H-NR7-A的氨基雜 或d)在一個(gè)單釜反應(yīng)(Eintopfreaktion)中，首先在堿存在下使式(V)H-NR7-A的氨基雜環(huán)化物與光氣反應(yīng)，然后反應(yīng)的中間體與式(II)的苯基磺酰胺反應(yīng)，或e)在堿存在下式(VII)的磺酰氯與其中M＝NH4、Na或K的氰酸酯M-OCN以及式(V)H-NR7-A的氨基雜環(huán)化物反 f)在堿存在下上述式(II)的磺酰胺與式(V’)的(硫代)異氰酸酯反應(yīng)W＝C＝N-A(V’)，在式(II)-(VII)和(V’)中的基團(tuán)R1-R7、A或W如在式(I)中的定義，在方法a)-e)中，最初獲得的是W＝O的式(I)化合物。
式(II)化合物和式(III)化合物的反應(yīng)優(yōu)選在堿催化下，在惰性有機(jī)溶劑，例如二氯甲烷、乙腈、二噁烷或THF存在下，在0℃和溶劑沸點(diǎn)之間進(jìn)行。使用的堿的實(shí)例為有機(jī)胺堿，如特別是R*＝(取代)苯基(參見(jiàn)EP-A-44 807)時(shí)，堿為1，8-二氮雜二環(huán)[5.4.0]十一-7-烯(DBU)，或特別是R*＝烷基(參見(jiàn)EP-A-166 516)時(shí)，堿為三甲基銨或三乙基銨。式(II)的磺酰胺是新化合物。其和其制備方法也是本發(fā)明的主題。以其中R2＝R3＝H和Q＝O的式(II)化合物為例，對(duì)其可能的制備方法在下面進(jìn)行了詳細(xì)的描述，且只要作一點(diǎn)改動(dòng)就可將上述方法用于其中R2和R3不是氫和/或Q不是O的化合物的制備。
采用文獻(xiàn)中已知的相似方法，以取代和未取代的甲基氨基苯磺酸(VIII)作為起始物(參見(jiàn)德國(guó)專(zhuān)利48 583,242頁(yè))時(shí)，最初通過(guò)重氮化作用和按Sandmeyer反應(yīng)用KCN/CuCN將其轉(zhuǎn)化成腈(IX)，將腈皂化，通過(guò)羧基的酯化作用和將磺基轉(zhuǎn)化成叔丁基-保護(hù)的磺酰胺基后得到作為中間體的磺酰胺(X)(見(jiàn)

圖1)。
圖1 此外，以取代或未取代的甲基硝基苯甲酸(XI)作為起始物，通過(guò)酯化作用、硝基的還原、重氮化作用和與SO2/CuCl偶聯(lián)(見(jiàn)H.Meerwein等人，Chem.Ber.90，841-1178(1957))和用叔丁基胺氨解可獲得式(X)的磺酰胺(見(jiàn)圖2)。
圖2 同樣磺酰胺(X)的制備可以取代或未取代的甲基硝基苯胺(XII)作為起始物。通過(guò)重氮化作用和與KCN/CuCN偶聯(lián)得到相應(yīng)的腈，其可通過(guò)氰基的水解并酯化成硝基苯甲酸酯(XIII)。然后可將圖2中所述的硝基轉(zhuǎn)化成叔丁基氨基磺?；?見(jiàn)圖3)。
圖3 為了制備式(II)的磺酰胺，可在式(X)化合物的側(cè)鏈進(jìn)行鹵化作用得到(XIV)，然后用胺或疊氮化物取代(XIV)上的鹵原子，接著還原得到芐基胺(XV’)，再對(duì)氨基官能化并通過(guò)已知的相似方法(例如用CF3COOH)除去叔丁基保護(hù)基得到磺酰胺(II’)(見(jiàn)圖4)。
圖4 類(lèi)似地，該方法步驟還可用于制備其它式(II)化合物，其中在最后一步中使用式(XV)化合物式(III)氨基甲酸酯可通過(guò)描述在南非專(zhuān)利申請(qǐng)82/5671和82/5045或EP-A-70 804(US-A-4,480101)或RD275056中的方法制備。
式(IV)化合物與氨基雜環(huán)(V)的反應(yīng)優(yōu)選在如二噁烷、乙腈或四氫呋喃的惰性的、質(zhì)子惰性溶劑中，在0℃至溶劑的沸點(diǎn)之間的溫度下進(jìn)行。所需的起始物(V)是文獻(xiàn)中已知的或可通過(guò)文獻(xiàn)中已知的方法制備的。式(IV)的苯基磺酰基氨基甲酸酯可通過(guò)類(lèi)似于US-A-4,684,393或US-A-4,743,290的方法獲得。
式(VI)的苯基磺?；惽杷狨タ赏ㄟ^(guò)類(lèi)似于US-A-4,481,029的方法制備并可與氨基雜環(huán)(V)反應(yīng)。
根據(jù)方法d)的式(V)化合物的光氣化作用優(yōu)選在如空間位阻的有機(jī)胺堿，例如三乙胺的存在下進(jìn)行。根據(jù)方法d)與式(II)化合物隨后進(jìn)行的反應(yīng)可通過(guò)類(lèi)似于已知的方法進(jìn)行(參見(jiàn)EP-A-232067)。
式(VII)的磺酰氯可通過(guò)常規(guī)方法從相應(yīng)的磺酸獲得，例如，在如乙腈和/或環(huán)丁砜的惰性溶劑中或不在溶劑中通過(guò)加熱至回流使鉀鹽與磷酰氯或亞硫酰氯反應(yīng)得到(參見(jiàn)Houben-Weyl-Klamann，“Methoden der organischen Chemie”，[有機(jī)化學(xué)方法]，第四版，E XI/2卷，1067-1073頁(yè)，ThiemeVerlag，Stuttgart，1985)。
通過(guò)類(lèi)似于化合物(XI)的反應(yīng)，相應(yīng)的磺酸可從適當(dāng)?shù)南趸衔铽@得。
可選擇地，在個(gè)別的情況下，磺酰氯(VII)可通過(guò)適當(dāng)取代的苯甲酸酯的磺化作用(+氯化作用)或氯磺化作用制備；氯磺化作用是采用Houben-Weyl-Klamann，“Methoden der organischenChemie”，[有機(jī)化學(xué)方法]，第四版，E XI/2卷，1067頁(yè)，ThiemeVerlag，Stuttgart，1985)；Houben-Weyl-Muller，“Methoden derorganischen Chemie”，[有機(jī)化學(xué)方法]，第四版，XI卷，563頁(yè)，Thieme Verlag，Stuttgart，1955)的類(lèi)似方法；磺化作用是采用Houben-Weyl-Klamann，“Methoden der organischenChemie”，[有機(jī)化學(xué)方法]，第四版，E XI/2卷，1055頁(yè)，ThiemeVerlag，Stuttgart，1985)；Houben-Weyl-Muller，“Methoden derorganischen Chemie”，[有機(jī)化學(xué)方法]，第四版，IX卷，435頁(yè)，Thieme Verlag，Stuttgart，1955)的類(lèi)似方法。
采用文獻(xiàn)中的已知方法(EP-A-232067，EP-A-166516)可獲得式(V’)的(硫代)異氰酸酯。(硫代)異氰酸酯(V’)與化合物(II)的反應(yīng)在-10℃至100℃，優(yōu)選20至200℃下，在諸如丙酮或乙腈的惰性的質(zhì)子惰性溶劑中，在適合的堿，例如N(C2H5)3或K2CO3的存在下進(jìn)行。
優(yōu)選于諸如水、甲醇或丙酮的惰性極性溶劑中，在0-100℃下制備式(I)化合物的鹽。根據(jù)本發(fā)明，適合制備鹽的堿的實(shí)例為堿金屬碳酸鹽，如碳酸鉀，堿金屬氫氧化物和堿土金屬氫氧化物，例如NaOH或KOH，或氨或乙醇胺。
在上述方法中所指的“惰性溶劑”為各種在各自的反應(yīng)條件下惰性的溶劑，但其不需要在所有的反應(yīng)條件下呈惰性。
根據(jù)本發(fā)明的式(I)化合物對(duì)多種經(jīng)濟(jì)上重要的單子葉和雙子葉有害植物具有極好的除草活性。本活性物質(zhì)還對(duì)從根莖、砧木根或其它多年生器官萌生的而且難于防治的多年生雜草具有有效的作用。在本文中，無(wú)論活性物質(zhì)在播種前、苗前或苗后使用都可以。
下面具體但非限定性地述及了根據(jù)本發(fā)明化合物可以防治的一些代表性的單子葉和雙子葉雜草的譜系。
活性物質(zhì)對(duì)其能有效發(fā)揮作用的雜草的實(shí)例為單子葉雜草一年生中的燕麥、黑麥草、看麥娘、虉草、稗、馬唐、狗尾草以及莎草屬和多年生冰草、狗牙根、白茅和蜀黍?qū)?，以及多年生莎草屬?br> 對(duì)雙子葉雜草能發(fā)揮作用的是，例如一年生的豬殃殃、堇菜、婆婆納、野芝麻、繁縷、莧、白芥、牽牛、母菊、麻和黃花稔屬，和多年生的旋花、薊、酸模和蒿屬。
根據(jù)本發(fā)明的活性物質(zhì)防治水稻生長(zhǎng)條件下的雜草非常有效，上述雜草如慈菇、澤瀉、荸薺、藨草和莎草屬。
如果在萌發(fā)前將根據(jù)本發(fā)明化合物施用到土壤表面，則或是能完全防止雜草幼苗萌發(fā)，或是雜草生長(zhǎng)到子葉階段后生長(zhǎng)停止且最終在三至四周后，雜草全部死亡。
如果將活性物質(zhì)在苗后施用到植物的綠色部分，在處理后短期內(nèi)植物生長(zhǎng)馬上停止且雜草植物停留在施藥時(shí)的生長(zhǎng)期，或一段時(shí)間后完全死亡，因此以這種方式將對(duì)作物有害的雜草競(jìng)爭(zhēng)及早、持繼地加以消除。
盡管對(duì)單子葉和雙子葉雜草具有極好所除草活性，根據(jù)本發(fā)明的化合物完全不損害經(jīng)濟(jì)作物或其損害很小，經(jīng)濟(jì)作物如小麥、大麥、黑麥、水稻、玉米、甜菜、棉花和大豆。根據(jù)上述原因，本發(fā)明的化合物非常適合在農(nóng)作物中選擇性地防治有害植物生長(zhǎng)。
另外，根據(jù)本發(fā)明的物質(zhì)對(duì)作物存在明顯的調(diào)節(jié)植物生長(zhǎng)的性質(zhì)。它們介入代謝的調(diào)節(jié)并因此可用來(lái)有針對(duì)性地影響植物中含有的物質(zhì)，和方便收獲，例如通過(guò)最初的干燥和生長(zhǎng)緊密。而且，它們可在不殺死植物的情況下，系統(tǒng)的防治和抑制不需要的植物生長(zhǎng)。在許多單子葉和雙子葉作物中，抑制植物生長(zhǎng)具有很大作用，這是因?yàn)檫@樣能減少或完全防止倒伏。
根據(jù)本發(fā)明的化合物可用于常規(guī)的制劑形式，如可濕性粉劑、可乳化濃縮物、可噴霧溶液、粉劑或顆粒劑。因此本發(fā)明還涉及含有式(I)化合物的除草和植物生長(zhǎng)調(diào)節(jié)組合物。
根據(jù)預(yù)定的生物和/或物理化學(xué)參數(shù)，可以多種方式配制式(I)化合物。因此可能的制劑為可濕性粉劑(WP)、水溶性粉劑(SP)、水溶性濃縮物、可乳化濃縮液(EC)、乳液(EW)如水包油型和油包水型乳液、可噴霧溶液、濃懸浮液(SC)、油基或水基分散液、油混溶液劑、膠囊懸浮液(CS)、粉劑(DP)、種子包衣劑、散播和土壤施用顆粒劑、微膠囊形式的顆粒劑(GR)、噴灑顆粒劑、包覆顆粒劑和吸收顆粒劑、水分散顆粒劑(WG)、水溶顆粒劑(SG)、ULV制劑、微膠囊和蠟劑。
上述單獨(dú)的制劑類(lèi)型原則上是已知的且描述在Winnacker-Kuchler，“Chemische Technologie”[化學(xué)技術(shù)]，7卷C.HauserVerlag Munich，第4版，1986；Wade van Valkenburg，“Pesticide Formulation”，Marcel Dekker N.Y.1973；K.Martens，“Spary Drying”手冊(cè)，第3版，1979，G.Goodwin Ltd.London。
制劑中所需要的助劑如惰性材料、表面活性劑、溶劑和其它添加劑也是已知的并描述在例如(Watkins，“Handbook ofInsecticide Dust Diluents and Carriers”，第二版，Darland Books，Caldwell N.J.，H.v.Olphen，“Introduction to Clay ColloidChemistry”，第二版，J.Wiley & Sons，N.Y.；C.Marsden，“Solvents Guide”，第二版，Interscience，N.Y.1963；McCutcheon’s“Detergents and Emulsifiers Annual”，MC Publ.Corp.，Ridgewood N.J.；Sisley and Wood，“Encyclopedia of SurfaceActive Agents”，Chem.Publ.Co.Inc.，N.Y.1964；Schonfeldt，“Grenzflchenaktive thylenoxidaddukte”[表面活性的環(huán)氧乙烷加成物]，Wiss.Verlagsgesell.，Stuttgart 1976；Winnacker-Küchler，“Chemische Technologie”[化學(xué)技術(shù)]，Volume 7，C.Hauser VerlagMunich，第4版，1986。
與其它已知農(nóng)藥活性成分如殺蟲(chóng)劑、殺螨劑、除草劑、殺菌基的組合物，以及與安全劑、肥料和/或生長(zhǎng)調(diào)節(jié)劑的組合物也可以上述制劑為基礎(chǔ)制備，例如以現(xiàn)用制劑或桶混合物的形式。
可濕性粉劑是能均勻分散于水中的制劑，且除了活性物質(zhì)外，其中還含有一些離子和/或非離子型表面活性劑(濕潤(rùn)劑，分散劑)，例如聚乙氧基化烷基酚、聚乙氧基化脂肪醇、聚乙氧基化脂肪胺、脂肪醇聚乙二醇醚硫酸鹽、烷基磺酸鹽、烷基苯磺酸鹽、木質(zhì)素磺酸鈉、2，2’-二萘基甲烷-6，6’-二磺酸鈉、二丁基萘磺酸鈉，或油?；?jīng)濟(jì)牛酯酸鈉(OleoylmethyltaurinsauresNatrium)，以及稀釋劑或惰性物質(zhì)。可濕性粉劑的制備是通過(guò)精細(xì)研磨除草活性物質(zhì)，例如在常規(guī)的設(shè)備如錘磨、吹磨和氣流磨中研磨，并在同時(shí)或隨后將其與制劑助劑混合。
可乳化濃縮液的制備是通過(guò)在添加一種或多種離子型和/或非離子型表面活性劑的條件下將活性物質(zhì)溶于有機(jī)溶劑中，有機(jī)溶劑例如丁醇、環(huán)己酮、二甲基甲酰胺、二甲苯和高沸點(diǎn)的芳香化合物或烴類(lèi)或有機(jī)溶劑的混合物。可使用的乳化劑的實(shí)例為烷基芳基磺酸鈣鹽如十二烷基苯磺酸鈣、或非離子型乳化劑，如脂肪酸聚乙二醇酯、烷基芳基聚乙二醇醚、脂肪醇聚乙二醇醚、環(huán)氧丙烷/環(huán)氧乙烷縮合產(chǎn)物、烷基聚醚、脫水山梨醇酯、如脫水山梨醇脂肪酸酯或“聚氧乙烯脫水山梨醇酯，諸如聚氧乙烯脫水山梨醇脂肪酸酯。
粉劑的制備是通過(guò)將活性物質(zhì)與細(xì)分離的固體物質(zhì)研磨而制備，固體物質(zhì)例如滑石或天然粘土，如高嶺土、膨潤(rùn)土、葉蠟石或硅藻土。
濃懸浮劑是以水或油為基礎(chǔ)的。它們的制備是例如通過(guò)借取常規(guī)的球磨濕磨和必要時(shí)加入上述其它類(lèi)型制劑中使用的表面活性劑來(lái)進(jìn)行的。
乳液，例如水包油型乳液(EW)的制備例如通過(guò)攪拌器、膠體磨和/或靜電磨的方式，使用含水的有機(jī)溶劑和如果需要的表面活性劑來(lái)制備，表面活性劑如上述其它類(lèi)型制劑中使用的表面活性劑。
顆粒劑的生產(chǎn)或是通過(guò)將活性物質(zhì)噴布在吸收性、造粒惰性材料上，或是借助于粘合劑將活性物質(zhì)的濃縮物涂敷在載體的表面，制備，載體如砂土、高嶺土和造粒惰性材料，粘合劑例如聚乙烯醇、聚丙烯酸鈉或礦物油。也可按常規(guī)的生產(chǎn)肥料顆粒的方法將活性物質(zhì)造粒，如果需要可為與肥料的混合物。
水分散顆粒劑通常是通過(guò)常規(guī)的方法制備，如噴霧干燥、流化床造粒、平板(Teller)造粒、用高速混合器混合和不需要固體惰性載體的擠壓。對(duì)于平板、流化床、擠壓器和噴布顆粒的制備，可參見(jiàn)“Spary Drying Handbook”第3版，1979，G.GoodwinLtd.，”London；J.E.Browning，“Agglomeration”，Chemical andEngineering 1967，147等頁(yè)；“Perry’s Chemical Engineer’sHandbook””，第5版，McGraw-Hill，New York 1973，8-57頁(yè)。
對(duì)于作物保護(hù)組合物制劑的詳細(xì)內(nèi)容例如參見(jiàn)G.C.Klingman，“Weed Control sa a Science”，John Wiley和Sons，Inc.，New York，1961，81-96頁(yè)和J.D.Freyer，S.A.Evans，“Weed ControlHandbook”，第5版，Blackweel ScientificPublications，Oxford，1968，101-103頁(yè)。
本農(nóng)用化學(xué)制劑通常含有0.1至99％重量和特別含有0.1至95％重量的式(I)活性物質(zhì)。活性物質(zhì)在可濕性粉劑中的濃度例如為大約10至90％重量；100％重量的剩余物由常規(guī)的制劑成分組成。在可乳化濃縮液的情況下，活性物質(zhì)的濃度可為大約1至90％重量，優(yōu)選5至80％重量。粉劑的制劑形式中含有1至30％重量，通常優(yōu)選5-20％重量的活性物質(zhì)，可噴霧液劑含有大約0.05至80，優(yōu)選2至50％重量的活性成分。在水分散顆粒劑的情況下活性物質(zhì)的含量部分的依賴(lài)于活性化合物為液體或固體和使用的造粒助劑、填料等。在水分散顆粒劑的情況下活性物質(zhì)的含量為例如1至95％重量，優(yōu)選10至80％重量。
另外，已述及的活性物質(zhì)的制劑如果適合可含有在各種情況下常規(guī)使用的粘著劑、濕潤(rùn)劑、分散劑、乳化劑、滲透劑、防腐劑、防凍劑、溶劑、填料、載體和著色劑、防泡劑、蒸發(fā)抑制劑和PH和粘度調(diào)節(jié)劑。
在混合制劑或桶混合物中的本發(fā)明活性物質(zhì)的混用組合物中可使用，例如描述在如Weed Research 26，441-445(1986)或“ThePesticide Manual”，第9版，The British Crop ProtectionCouncil，1990/91，Bracknell，England，和其中所引文獻(xiàn)描述的已知活性物質(zhì)?？膳c式(I)化合物混用的文獻(xiàn)中已知的除草劑的實(shí)例為下述活性物質(zhì)(注意化合物或是以其根據(jù)國(guó)際標(biāo)準(zhǔn)化組織(ISO)提供的通用名給出或是以化學(xué)名給出，如果需要還連帶通用編碼)乙草胺、三氟羧草醚、苯草醚、氟草醚酯，即[[[1-[5-[2-氯-4-(三氟甲基)苯氧基]-2-硝基苯基]-2-甲氧基亞乙基]氨基]氧]乙酸及其甲基酯、甲草胺、枯殺達(dá)、莠滅津、amidosulfuron、amitrol、AMS，即氨基磺酸銨、莎稗磷、黃草靈、莠去津、azimsulfurone(DPX-A8947)、疊氮津、燕麥靈、BAS516H，即5-氟-2-苯基-4H-3，1-苯并惡嗪-4-酮、草除靈、氟草胺、呋草黃、芐嘧磺隆、地散磷、滅草松、吡草酮、benzofluor、新燕靈、噻草隆、雙丙氨酰膦、甲羧除草醚、除草定、溴丁酰草胺、殺草全、溴苯腈、bromuron、buminafos、busoxinone、丁草胺、草胺磷、丁烯草胺、草噻醚、地樂(lè)胺、丁草特、cafenstrole(CH-900)、卡草胺、碘草酮(ICI-A0051)、草毒死，即2-氯-N，N-二-2-丙烯基乙酰胺、草克死，即2-氯烯丙基二乙基二硫代氨基甲酸酯、氟硝醚、草滅平、chlorazifop-butyl、Chlormesulon(ICI-A0051)、氯溴隆、氟草靈、伐克草、氯甲丹、殺草敏、氯嘧磺隆、草枯醚、綠麥隆、枯草隆、氯苯胺靈、綠磺隆、敵草索、草克樂(lè)、惡庚草烷、醚磺隆、烯草酮、clodinafop及其酯衍生物(例如clodinafop-propargyl)、廣滅靈、稗草胺、Cloproxydim、clopyralid、cumyluron(JC 940)、氰草津、環(huán)莠特、cyclosulfamuron(AC 104)、噻草酮、環(huán)莠隆、cyhalofop及其酯衍生物(例如丁基酯，DEH-112)、對(duì)草快、環(huán)草津、環(huán)唑草胺、daimuron、2，4-滴丁酸、茅草枯、異苯敵草、敵草凈、燕麥敵、麥草畏、敵草腈、2，4-滴丙酸、禾草靈、及其酯如甲基禾草靈、安塔、枯莠隆、野燕枯、吡氟草胺、dimefuron、克草胺、戊草津、dimethenamide(SAN-582H)、敵苯達(dá)松、dimethipin、dimetrasulfuron、敵樂(lè)胺、地樂(lè)散、地樂(lè)硝酚、雙苯酰草胺、殺草凈、敵草快、氟硫草定、敵草隆、二硝甲酚、草止津、氟草酮，即5-氰基-1-(1，1-二甲基乙基)-N-甲基-1H-吡唑-4-甲酰胺、草藻滅、撲草滅、禾草畏、丁氟硝草、ethametsulfuron-methyl、噻二唑隆、乙嗪草酮、唑啶草、F5231，即N-[2-氯-4-氟-5-[4-(3-氟丙基)-4，5-二氫-5-氧-1H-四唑-1-基]苯基]乙烷磺酰胺、ethoxyfen及其酯(例如乙基酯，HN-252)、etobenzanid(HW52)、2，4，5-滴丙酸、fenoxan、噁唑禾草靈和高噁唑禾草靈及其酯，例如fenoxaprop-P-ethyl和fenoxaprop-ethyl、fenoxydim、黃草隆、甲氟燕靈、啶嘧磺隆、吡氟禾草靈和精吡氟禾草靈及其酯，例如fluazifop-butyl和fluazifop-P-butyl、氟消草、flumetsulam、伏草隆、flumiclorac及其酯(例如苯基酯，S-23031)、flumioxazin(S-482)、flumipropyn、flupoxam(KNW-739)、fluorodifen、fluoroglycofen-ethyl、氟胺磺隆(UBIC-4243)、氟草同、fluroehloridone、fluroxypyr、flurtamone、氟磺胺草醚、膦銨素、氟呋草醚、草胺膦、草甘膦、halosaten、halosulfuron及其酯(例如甲基酯，NC-319)、吡氟乙草靈及其酯、吡氟氯禾靈(＝R-haloxyfop)及其酯、環(huán)嗪酮、咪草酯、滅草煙、滅草喹、及其鹽如銨鹽、imazethamethapyr、咪草胺、imazosulfuron、碘苯腈、丁環(huán)隆、異樂(lè)靈、異丙隆、異噁隆、異惡草胺、isoxapyrifop、卡草靈、克闊樂(lè)、環(huán)草定、利谷隆、二甲四氯、二甲四氯丁酸、二甲四氯丙酸、苯噻草胺、氟草磺、苯嗪草、吡草胺、噻唑隆、威百畝、滅草定、去草酮、methyldymron、metabenzuron、methobenzuron、秀谷隆、丙草胺、metosulam(XRD 511)、甲氧隆、賽克津、甲黃隆、抑草丹、禾草特、殺草利、二氫硫酸單脲、綠谷隆、滅草隆、MT128，即6-氯-N-(3-氯-2-丙烯基)-5-甲基-N-苯基-3-噠嗪胺(pyridazinamin)、MT 5959，即N-[3-氯-4-(1-甲基乙基)-苯基]-2-甲基戊酰胺、草萘胺、抑草生、NC310，即4-(2，4-二氯苯甲酰基)-1-甲基-5-芐基氧吡唑、草不隆、煙嘧磺隆、吡氯草胺、nitralin、除草醚、nitroflurofen、norflurazon、orbencarb、磺禾靈、惡霜靈(RP-020630)、惡草靈、氟消草醚、對(duì)草快、克草猛、胺硝草、氟草磺胺、敵克草、二苯乙草、毒莠定、哌草磷、piributicarb、pirifenop-butyl、丙草胺、氟嘧磺隆、環(huán)氰津、prodiamine、卡樂(lè)施、丙草止津、2，4，5-涕、撲草凈、metryn、撲草胺、敵稗、喔草酯及其酯、撲滅津、苯胺靈、propisoehlor、拿草特、prosulfalin、殺草丹、prosulfuron(CGA-152005)、廣草胺、pyrazolinate、殺草敏、吡嘧磺隆、芐草唑、達(dá)草酯、pyrithiobac(KIH-2031)、pyroxofop及其酯(即炔丙基酯)、二氯喹啉酸、喹草酸、quinofop及其酯衍生物、喹禾靈和quizalofop及其酯衍生物、即quizalofop-ethyl、quizalofop-P-tefuryl和-ethyl、renriduron、rimsulfuron(DPX-E 9636)、S275，即2-[4-氯-2-氟-5-(2-丙炔氧基)-苯基]4，5，6，7-私氫-2H-吲唑、密草通、烯禾定、環(huán)莠隆、西馬津、西草凈、氟萘草酯、即2-[[7-[2-氯-4-(三氟甲基)-苯氧基]-2-萘基]氧]丙酸及其甲基酯、sulfentrazon(FMC-97385，f-6285)、sultazuron、嘧磺隆、sulfosate(ICI-A0224)、三氟醋酸、tebutam(GCP-5544)、丁唑隆、特草定、牙根靈、猛殺草、甲氧去草凈、特丁津、去草凈、TFH450，即N，N-二乙基-3-[(2-乙基-6-甲基苯基)-磺?；鵠-1H-1，2，4-三唑-1-甲酰胺、thenylchlor(NSK-850)、噻唑隆、thizopyr(Mon-13200)、thidiazimin(SN-124085)、嘧黃隆、殺草丹、丁草威、肟草酮、野麥畏、triasulfuron、triazofenamide、teibenuron-methyl、定草酯、tridiphane、草達(dá)津、氟樂(lè)靈、醚苯黃隆及其酯(例如甲基酯，DPX-66037)、三甲隆、tsitodef、滅草猛、WL 110547，即5-苯氧基-1-[3-(三氟甲基)-苯基]-1H-四唑、UBH-509、D-489、LS82-556、KPP-300、NC-324、NC-330、KH-218、DPX-N8189、SC-0774、DOWCO-535、DK-8910、V-53482、PP-600、MBH-001、KIH-9201、ET-751、KIH-6127和KIH-2023。
在使用時(shí)如果需要可以常規(guī)方式將市售形式的制劑稀釋?zhuān)缬盟♂尶蓾裥苑蹌?、可乳化濃縮液、分散和水分散顆粒劑，粉劑、用于土壤施用和撒播的顆粒劑以及可噴霧液劑，在使用前通常不需要用其它惰性物質(zhì)稀釋。
式(I)化合物的所需施用劑量可根據(jù)外部條件如溫度、濕度、和使用除草劑的性質(zhì)而變化。使用劑量可在很寬的范圍內(nèi)變化，例如0.001至10.0kg/ha或更多的活性物質(zhì)；可是優(yōu)選0.005至5kg/ha。A.化學(xué)實(shí)施例縮寫(xiě)除非另外指明，百分比和量比指的是重量。
i.v.＝在減壓條件下h＝小時(shí)實(shí)施例A1N-叔丁基-5-溴甲基-2-甲氧基羰基苯磺酰胺將在420ml四氯甲烷中的54.8g(192mmol)的N-叔丁基-2-甲氧羰基-5-甲基苯磺酰胺在氮保護(hù)氣下在加入36g(202mmol)的N-溴琥珀酰亞胺和0.5g的偶氮二異丁腈(AIBN)之后，在用日光燈照射的同時(shí)加熱回流6-8小時(shí)。然后過(guò)濾溶液，并依次用亞硫酸氫鈉溶液、碳酸氫鈉溶液和水沖洗，用Na2SO4充分干燥并蒸發(fā)至干i.v.。從二異丙基醚/乙酸乙酯結(jié)晶剩余物，得到41.9g(57％)的N-叔丁基-5-溴甲基-2-甲氧基羰基苯磺酰胺，F(xiàn)p.88-90℃。
實(shí)施例A2N-叔丁基-5-疊氮基甲基-2-甲氧基羰基苯磺酰胺將25.5g(70mmol)的N-叔丁基-5-溴甲基-2-甲氧基羰基苯磺酰胺和5.9g(90mmol)的疊氮化鈉在240ml乙醇中的溶液加熱回流6小時(shí)。然后將溶液蒸發(fā)至干并用水/乙酸乙酯提取剩余物。用二異丙醚浸提粗產(chǎn)物，得到16.6g(72.5％)的N-叔丁基-5-疊氮基甲基-2-甲氧基羰基苯磺酰胺，F(xiàn)p.63-65℃。
實(shí)施例A3N-叔丁基-5-氨基甲基-2-甲氧基羰基苯磺酰胺將16.3g(50mmol)的N-叔丁基-5-疊氮基甲基-2-甲氧基羰基苯磺酰胺溶于300ml甲醇中并經(jīng)Pd/C(5％)氫化。將混合物過(guò)濾并蒸發(fā)至干。將獲得所粗產(chǎn)物通過(guò)硅膠粒洗脫純化，用乙酸乙酯/甲醇4∶1作為洗脫液。獲得粘稠油狀的11.2g(74％)N-叔丁基-5-氨基甲基-2-甲氧基羰基苯磺酰胺。
1H NMR(100MHz，CDCl3)δ＝1,25(s，9H，C(CH3)3)，1,80 (bs，2H，NH2)，3,95(s，3H，OCH3)，4,00(s，2H，Ar-CH2)，6,20(bs，1H，SO2NH)，7,58(dd，1H，Ar-H)，7,80(d，1H，Ar-H)，8,10(dd，1H，Ar-H).
實(shí)施例A4N-叔丁基-5-乙酰氨基甲基-2-甲氧基羰基苯磺酰胺將0.63g(8mmol)的乙酰氯溶于10ml二氯甲烷中并滴加到冷卻到0℃的、2.01g(6.7mmol)N-叔丁基-5-氨基甲基-2-甲氧基羰基苯磺酰胺和0.93ml(6.7mmol)三乙胺的30ml二氯甲烷溶液中，在室溫下攪拌混合物2小時(shí)。用水洗滌反應(yīng)溶液，干燥并蒸發(fā)至干i.v.。獲得粘稠油狀的2.1g(91％)的N-叔丁基-5-乙酰氨基甲基-2-甲氧基羰基苯磺酰胺。
1H NMR(100MHz，CDCl3)δ＝1,25(s，9H，C(CH3)3)，2,05(s，3H，COCH3)，3,95(s，3H，OCH3)，4,50(s，2H，Ar-CH2)，6,15(s，1H，SO2NH)，6,38(bt，1H，NH)，7,47(dd，1H，Ar-H)，7,75(d，1H，Ar-H)，7,95(dd，1H，Ar-H).
實(shí)施例A55-乙酰氨基甲基-2-甲氧基羰基苯磺酰胺將2.09g(6.1mmol)N-叔丁基-5-乙酰氨基甲基-2-甲氧基羰基苯磺酰胺的25ml三氟乙酸溶液在室溫下攪拌14小時(shí)，然后蒸發(fā)至干。從乙酸乙酯中結(jié)晶剩余物，得到1.33g(76％)的5-乙酰氨基甲基-2-甲氧基羰基苯磺酰胺，F(xiàn)p.173-175℃。
實(shí)施例A6N-[4，6-(二甲氧基嘧啶-2-基)氨基羰基]-5-乙酰氨基甲基-2-甲氧基羰基苯磺酰胺將0.69g(4.54mmol)的1，8-二氮雜二環(huán)[5.4.0]十一-7-烯(DBU)在0℃加入到1.3g(4.54mmol)的5-乙酰氨基甲基-2-甲氧羰基苯磺酰胺和1.25g(4.54mmol)的N-(4，6-二甲氧基嘧啶-2-基)苯基氨基甲酸酯的20ml乙腈懸浮液中。在室溫下2小時(shí)后，用水和乙醚稀釋混合物，用鹽酸酸化到pH 1-2，過(guò)濾出所得沉淀并干燥。獲得1.32g(62％)的N-[4，6-(二甲氧基嘧啶-2-基)氨基羰基]-5-乙酰氨基甲基-2-甲氧基羰基苯磺酰胺，mp.149-150℃。
采用實(shí)施例A1-A6的類(lèi)似方法，可獲得例示于下述表1-4中的式(I)化合物(W＝O，A＝嘧啶基或三嗪基)。在表中Fp.＝熔點(diǎn)℃Vb＝化合物號(hào)＝實(shí)施例號(hào)Me＝甲基＝CH3Et＝乙基Bu＝n-Bu＝n-丁基＝n-C4H9Ph＝苯基表1 Vb. R1R4R5R7X YZ Fp.℃1CO2CH3H CHO H OCH3OCH3CH 124-1252″ ″″H OCH3CH3CH3″ ″″H CH3CH3CH4″ ″″H CH3OC2H5CH5″ ″″H OCH3OCH3N6″ ″″H OCH3CH3N7″ ″″H OCH3Cl CH8″ ″″H OCF2H CH3CH9″ ″″H OCF2H OCF2H CH10 ″ ″″H OCH3Br CH11 ″ ″″H OCH3OC2H5CH12 ″ ″″H OCH3SCH3CH13 ″ ″″H OCH3OC2H5N14 ″ ″″H OCH3OC3H7CH15 ″ ″″H CH3Cl CH16 ″ ″″H Cl OC2H5CH17 ″ ″″H OC2H5OC2H5CH18 ″ ″″H C2H5OCH3CH19 ″ ″″H CF3OCH3CH20 ″ ″″H OCH2CF3CH3CH21 ″ ″″H OCH2CF3OCH3CH22 ″ ″″H OCH2CF3OCH2CF3CH23 ″ ″″H OCH2CF3OCH3NVb. R1R4R5R7X Y ZFp.C24″″″ H OCH3CH(OCH3)2CH25″″″ CH3OCH3OCH3CH26″″″ CH3OCH3CH3N27″H COCH3H OCH3OCH3CH 149-15028″″″ H OCH3CH3CH29″″″ H CH3CH3CH30″″″ H CH3OC2H5CH31″″″ H OCH3OCH3N32″″″ H OCH3CH3N33″″″ H OCH3Cl CH34″″″ H OCF2H CH3CH35″″″ H OCF2H OCF2H CH36″″″ H OCH3Br CH37″″″ H OCH3OC2H5CH38″″″ H OCH3SCH3CH39″″″ H OCH3OC2H5N40″″″ H OCH3OC3H7CH41″″″ H CH3Cl CH42″″″ H Cl OC2H5CH43″″″ H OC2H5OC2H5CH44″″″ H C2H5OCH3CH45″″″ H CF3OCH3CH46″″″ H OCH2CF3CH3CH47″″″ H OCH2CF3OCH3CH48″″″ H OCH2CF3OCH2CF3CH49″″″ H OCH2CF3OCH3N50″″″ H OCH3CH(OCH3)2CH51″″″ CH3OCH3OCH3CH52″″″ CH3OCH3CH3N53″CH3CHO H OCH3OCH3CH 171-17554″″″ H OCH3CH3CH 135-14055″″″ H CH3CH3CH 123-12656″″″ H CH3OC2H5CH57″″″ H OCH3OCH3N58″″″ H OCH3CH3N 105Vb. R1R4R5R7X YZFp.C59″″″ H OCH3Cl CH 125-13060″″″ H OCF2H CH3CH61″″″ H OCF2H OCF2H CH62″″″ H OCH3Br CH63″″″ H OCH3OC2H5CH64″″″ H OCH3SCH3CH65″″″ H OCH3OC2H5N66″″″ H OCH3OC3H7CH67″″″ H CH3Cl CH68″″″ H Cl OC2H5CH69″″″ H OC2H5OC2H5CH70″″″ H C2H5OCH3CH71″″″ H CF3OCH3CH72″″″ H OCH2CF3CH3CH73″″″ H OCH2CF3OCH3CH74″″″ H OCH2CF3OCH2CF3CH75″″″ H OCH2CF3OCH3N76″″″ H OCH3CH(OCH3)2CH77″″″ CH3OCH3OCH3CH78″″″ CH3OCH3CH3N79″CH3COCH3H OCH3OCH2CH 146-14980″″″ H OCH3CH3CH81″″″ H CH3CH3CH82″″″ H CH3OC2H5CH83″″″ H OCH3OCH3N84″″″ H OCH3CH3N85″″″ H OCH3Cl CH86″″″ H OCF2H CH3CH87″″″ H OCF2H OCF2H CH88″″″ H OCH3Br CH89″″″ H OCH3OC2H5CH90″″″ H OCH3SCH3CH91″″″ H OCH3OC2H5N92″″″ H OCH3OC3H7CH93″″″ H CH3ClCHVb. R1R4R5R7X YZ Fp.℃94″″″ H Cl OC2H5CH95″″″ H OC2H5OC2H5CH96″″″ H C2H5OCH3CH97″″″ H CF3OCH3CH98″″″ H OCH2CF3CH3CH99″″″ H OCH2CF3OCH3CH100 ″″″ H OCH2CF3OCH2CF3CH101 ″″″ H OCH2CF3OCH3N102 ″″″ H OCH3CH(OCH3)2CH103 ″″″ CH3OCH3OCH3CH104 ″″″ CH3OCH3CH3N105 ″HSO2CH3H OCH3OCH3CH 192-194106 ″″″ H OCH3CH3CH107 ″″″ H CH3CH3CH108 ″″″ H OCH3OCH3N109 ″″″ H OCH3CH3N110 ″″″ H OC2H5NHCH3N111 ″″″ CH3OCH3OCH3CH112 ″″″ CH3OCH3CH3N113 ″CH3SO2CH3H OCH3OCH3CH 107-109114 ″″″ H OCH3CH3CH115 ″″″ H CH3CH3CH116 ″″″ H OCH3OCH3N117 ″″″ H OCH3CH3N118 ″″″ H OC2H5NHCH3N119 ″″″ CH3OCH3OCH3CH120 ″″″ CH3OCH3CH3N121 ″OHCHO H OCH3OCH3CH122 ″″″ H OCH3CH3CH123 ″″″ H CH3CH3CH124 ″″″ H OCH3OCH3N125 ″″″ H OCH3CH3N126 ″″″ H OC2H5NHCH3N127 ″″″ CH3OCH3OCH3CH128 ″″″ CH3OCH3CH3NVb.R1R4R5R7X Y ZFp.℃129″OCH3CHO HOCH3OCH3CH 142-145130″″″ HOCH3CH3CH131″″″ HCH3CH3CH132″″″ HOCH3OCH3N133″″″ HOCH3CH3N134″″″ HOC2H5NHCH3N135″″″ CH3OCH3OCH3CH136″″″ CH3OCH3CH3N137″OHCOCH3HOCH3OCH3CH138″″″ HOCH3CH3CH139″″″ HCH3CH3CH140″″″ HOCH3OCH3N141″″″ HOCH3CH3N142″″″ HOC2H5NHCH3N143″″″ CH3OCH3OCH3CH144″″″ CH3OCH3CH3N145″OCH3COCH3HOCH3OCH3CH 195-196146″″″ HOCH3CH3 CH147″″″ HCH3CH3CH148″″″ HOCH3OCH3N149″″″ HOCH3CH3N150″″″ HOC2H5NHCH3N151″″″ CH3OCH3OCH3CH152″″″ CH3OCH3CH3N153″H COC2H5HOCH3OCH3CH 150-152154″″″ HOCH3CH3CH155″″″ HOCH3OCH3N156″″″ HOCH3CH3N157″ CH3″ HOCH3OCH3CH158″″″ HOCH3CH3CH159″″″ HOCH3OCH3N160″″″ HOCH3CH3N161″H COCH2OCH3HOCH3OCH3CH162″″″ HOCH3CH3CH163″″″ HOCH3OCH3NVb.R1R4R5R7X Y Z Fp.℃164″″″HOCH3CH3N165″CH3″ HOCH3OCH3CH166″″″HOCH3CH3CH167″″″HOCH3OCH3N168″″″HOCH3CH3N169″H COCO2C2H5HOCH3OCH3CH170″″″HOCH3CH3CH171″″″HOCH3OCH3N172″″″HOCH3CH3N173″CH3″ HOCH3OCH3CH174″″″HOCH3CH3CH175″″″HOCH3OCH3N176″″″HOCH3CH3N177″H COCF3HOCH3OCH3CH 158178″″″HOCH3CH3CH179″″″HOCH3OCH3N180″″″HOCH3CH3N181″CH3″HOCH3OCH3CH 144-147182″″″HOCH3CH3CH183″″″HOCH3OCH3N184″″″HOCH3CH3N185″H COOCH3HOCH3OCH3CH 160-161186″″″HOCH3CH3CH187″″″HOCH3OCH3N188″″″HOCH3CH3N189″CH3″HOCH3OCH3CH 157-159190″″″HOCH3CH3CH191″″″HOCH3OCH3N192″″″HOCH3CH3N193″H CONHC2H5HOCH3OCH3CH194″″″HOCH3CH3CH195″″″HOCH3OCH3N196″″″HOCH3CH3N197″CH3″HOCH3OCH3CH198″″″HOCH3CH3CHVb.R1R4R5R7X Y Z Fp.℃199″″″ HOCH3OCH3N200″″″ HOCH3CH3N201″H CSNHC2H5HOCH3OCH3CH202″″″ HOCH3CH3CH203″″″ HOCH3OCH3N204″″″ HOCH3CH3N205″CH3″ HOCH3OCH3CH206″″″ HOCH3CH3CH207″″″ HOCH3OCH3N208″″″ HOCH3CH3N209″H SO2NHCH3HOCH3OCH3CH210″″″ HOCH3CH3CH211″″″ HOCH3OCH3N212″″″ HOCH3CH3N213″ CH3″ HOCH3OCH3CH 171-173214″″″ HOCH3CH3CH215″″″ HOCH3OCH3N216″″″ HOCH3CH3N217″H SO2N(CH3)2HOCH3OCH3CH 162218″″″ HOCH3CH3CH219″″″ HOCH3OCH3N220″″″ HOCH3CH3N221″ CH3″ HOCH3OCH3CH 127-129222″″″ HOCH3CH3CH223″″″ HOCH3OCH3N224″″″ HOCH3CH3N225″-CH2CH2CH2CO- HOCH3OCH3CH226″ ″ HOCH3CH3CH227″ ″ HOCH3OCH3N228″ ″ HOCH3CH3N229″-CH2CH2CH2SO2- HOCH3OCH3CH230″ ″ HOCH3CH3CH231″ ″ HOCH3OCH3N232″ ″ HOCH3CH3N233″-CH2CH2CH2CH2CO- HOCH3OCH3CHVb.R1R4R5R7X Y ZFp.℃234″ ″ HOCH3CH3CH235″ ″ HOCH3OCH3N236″ ″ HOCH3CH3N237″-CH2CH2CH2CH2SO2- H OCH3OCH3CH238″ ″ HOCH3CH3CH239″ ″ HOCH3OCH3N240″ ″ HOCH3CH3N241″-CH2CH2OCH2CH2- HOCH3OCH3CH242″ ″ HOCH3CH3CH243″ ″ HOCH3OCH3N244″ ″ HOCH3CH3N245″H COC3H7HOCH3OCH3CH246″″ ″ HOCH3CH3CH247″″ ″ HOCH3OCH3N248″″ ″ HOCH3CH3N249″CH3″ HOCH3OCH3CH250″″ ″ HOCH3CH3CH251″″ ″ HOCH3OCH3N252″″ ″ HOCH3CH3N253″H COCH2ClHOCH3OCH3CH 144-145254″″ ″ HOCH3CH3CH255″″ ″ HOCH3OCH3N256″″ ″ HOCH3CH3N257″CH3″ HOCH3OCH3CH 138-140258″″ ″ HOCH3CH3CH259″″ ″ HOCH3OCH3N260″″ ″ HOCH3CH3N261″H COCHCl2HOCH3OCH3CH262″″ ″ HOCH3CH3CH263″″ ″ HOCH3OCH3N264″″ ″ HOCH3CH3N265″CH3″ HOCH3OCH3CH266″″ ″ HOCH3CH3CH267″″ ″ HOCH3OCH3N268″″ ″ HOCH3CH3NVb.R1R4R5R7X Y Z Fp.℃269″H COCCl3HOCH3OCH3CH270″″ ″ HOCH3CH3CH271″″ ″ HOCH3OCH3N272″″ ″ HOCH3CH3N273″CH3″ HOCH3OCH3CH274″″ ″ HOCH3CH3CH275″″ ″ HOCH3OCH3N276″″ ″ HOCH3CH3N277″H COCH＝CH2HOCH3OCH3CH278″″ ″ HOCH3CH3CH279″″ ″ HOCH3OCH3N280″″ ″ HOCH3CH3N281″CH3″ HOCH3OCH3CH282″″ ″ HOCH3CH3CH283″″ ″ HOCH3OCH3N284″″ ″ HOCH3CH3N285″H COC＝CHHOCH3OCH3CH286″″ ″ HOCH3CH3CH287″″ ″ HOCH3OCH3N288″″ ″ HOCH3CH3N289″CH3″ HOCH3OCH3CH290″″ ″ HOCH3CH3CH291″″ ″ HOCH3OCH3N292″″ ″ HOCH3CH3N293″H COC6H5HOCH3OCH3CH294″″ ″ HOCH3CH3CH295″″ ″ HOCH3OCH3N296″″ ″ HOCH3CH3N297″CH3″ HOCH3OCH3CH298″″ ″ HOCH3CH3CH299″″ ″ HOCH3OCH3N300″″ ″ HOCH3CH3N301″SO2C6H5SO2C6H5HOCH3OCH3CH302″″ ″ HOCH3CH3CH303″″ ″ HOCH3OCH3NVb.R1R4R5R7X Y Z Fp.℃304″″ ″ HOCH3CH3N305″SO2CH3SO2CH3HOCH3OCH3CH306″″ ″ HOCH3CH3CH307″″ ″ HOCH3OCH3N308″″ ″ HOCH3CH3N309″HCOCH2Br HOCH3OCH3CH310″″ ″ HOCH3CH3N311″CH3″ HOCH3OCH3CH312″″ ″ HOCH3CH3N313″HCOCH2F HOCH3OCH3CH314″″ ″ HOCH3CH3N315″CH3″ HOCH3OCH3CH316″″ ″ HOCH3CH3N317″HCOCH2C＝CH HOCH3OCH3CH318″″ ″ HOCH3CH3N319″CH3″ HOCH3OCH3CH320″″ ″ HOCH3CH3N321″HCOCO2CH3HOCH3OCH3CH322″″ ″ HOCH3CH3N323″CH3″ HOCH3OCH3CH324″″ ″ HOCH3CH3N325″HCO2C2H5HOCH3OCH3CH326″″ ″ HOCH3CH3N327″CH3″ HOCH3OCH3CH328″″ ″ HOCH3CH3N329″HCOSCH3HOCH3OCH3CH330″″ ″ HOCH3CH3N331″CH3″ HOCH3OCH3CH332″″ ″ HOCH3CH3N333″HCSOCH3HOCH3OCH3CH334″″ ″ HOCH3CH3N335″CH3″ HOCH3OCH3CH336″″ ″ HOCH3CH3N337″HCSSCH3HOCH3OCH3CH338″″ ″ HOCH3CH3NVb. R1R4R5R7X Y Z Fp.℃339 ″CH3″ H OCH3OCH3CH340 ″″″ H OCH3CH3N341 ″H COCH(CH3)2H OCH3OCH3CH342 ″″″ H OCH3CH3N343 ″CH3″ H OCH3OCH3CH344 ″″″ H OCH3CH3N345 ″H COC(CH3)3H OCH3OCH3CH346 ″″″ H OCH3CH3N347 ″CH3″ H OCH3OCH3CH348 ″″″ H OCH3CH3N349 ″H CO-環(huán)丙基H OCH3OCH3CH350 ″″″ H OCH3CH3N351 ″CH3″ H OCH3OCH3CH352 ″″″ H OCH3CH3N353 ″H CO環(huán)丁基 H OCH3OCH3CH354 ″″″ H OCH3CH3N355 ″CH3″ H OCH3OCH3CH356 ″″″ H OCH3CH3N357 ″H CO-環(huán)戊基H OCH3OCH3CH358 ″″″ H OCH3CH3N359 ″CH3″ H OCH3OCH3CH360 ″″″ H OCH3CH3N361 ″H CO-環(huán)己基H OCH3OCH3CH362 ″″″ H OCH3CH3N363 ″CH3″ H OCH3OCH3CH364 ″″″ H OCH3CH3N365 ″H CONHCH2CH2Cl H OCH3OCH3CH366 ″″″ H OCH3CH3N367 ″CH3″ H OCH3OCH3CH368 ″″″ H OCH3CH3N369 ″H CSNHCH2CH2Cl H OCH3OCH3CH370 ″″″ H OCH3CH3N371 ″CH3″ H OCH3OCH3CH372 ″″″ H OCH3CH3N373 ″H CONH-n-C4H9H OCH3OCH3CHVb.R1R4R5R7XY Z Fp.℃374″″ ″ H OCH3CH3N375″CH3″ H OCH3OCH3CH376″″ ″ H OCH3CH3N377″H CSNHCH3H OCH3OCH3CH378″″ ″ H OCH3CH3N379″CH3″ H OCH3OCH3CH380″″ ″ H OCH3CH3N381″H CSNHCH2CH＝CH2H OCH3OCH3CH382″″ ″ H OCH3CH3N383″CH3″ H OCH3OCH3CH384″″ ″ H OCH3CH3N385″CH3CSNHCH2COCH3H OCH3OCH3CH386″″ ″ H OCH3CH3N387″CH3CSNHCH2COC2H5H OCH3OCH3CH388″″ ″ H OCH3CH3N389″CH3CONHCH2COCH3H OCH3OCH3CH390″″ ″ H OCH3CH3N391″CH3CONHCH2COC2H5H OCH3OCH3CH392″″ ″ H OCH3CH3N393″-CONHCH2CO- H OCH3OCH3CH394″″ H OCH3CH3N395″H SO2CH2F H OCH3OCH3CH396″″ ″ H OCH3CH3N397″CH3″ H OCH3OCH3CH398″″ ″ H OCH3CH3N399″H SO2CF3H OCH3OCH3CH400″″ ″ H OCH3CH3N401″CH3″ H OCH3OCH3CH402″″ ″ H OCH3CH3N403″H SO2C2H5H OCH3OCH3CH404″″ ″ H OCH3CH3N405″CH3″ H OCH3OCH3CH406″″ ″ H OCH3CH3N407″H SO2-n-C3H7H OCH3OCH3CH408″″ ″ H OCH3CH3NVb.R1R4R5R7X Y Z Fp.℃409″CH3″ HOCH3OCH3CH410″″ ″ HOCH3CH3N411″OH COC2H5HOCH3OCH3CH412″″ ″ HOCH3CH3N413″OCH3″ HOCH3OCH3CH414″″ ″ HOCH3CH3N415″OH COCH2ClHOCH3OCH3CH416″″ ″ HOCH3CH3N417″OCH3″ HOCH3OCH3CH418″″ ″ HOCH3CH3N419″OH COCF3HOCH3OCH3CH420″″ ″ HOCH3CH3N421″OCH3″ HOCH3OCH3CH 159-161422″″ ″ HOCH3CH3N423″OH COCH2OCH3HOCH3OCH3CH424″″ ″ HOCH3CH3N425″OCH3″ HOCH3OCH3CH 130-131426″″ ″ HOCH3CH3N427″OH COCO2C2H5HOCH3OCH3CH428″″ ″ HOCH3CH3N429″OCH3″ HOCH3OCH3CH 158-159430″″ ″ HOCH3CH3N431″OH COOCH3HOCH3OCH3CH432″″ ″ HOCH3CH3N433″OCH3″ HOCH3OCH3CH 137-138434″″ ″ HOCH3CH3N435″OH Cyclopropyl HOCH3OCH3CH436″″ ″ HOCH3CH3N437″OCH3″ HOCH3OCH3CH 118-120438″″ ″ HOCH3CH3N439″OH COC6H5HOCH3OCH3CH440″″ ″ HOCH3CH3N441″OCH3″ HOCH3OCH3CH442″″ ″ HOCH3CH3N443″OH COCH(CH3)2HOCH3OCH3CHVb.R1R4R5R7X Y ZFp.℃444″″″ H OCH3CH3N445″OCH3″H OCH3OCH3CH 126-128446″″″H OCH3CH3N447″OHCOCH＝CH2H OCH3OCH3CH448″″″H OCH3CH3N449″OCH3″H OCH3OCH3CH450″″″H OCH3CH3N451″OHCOC＝CH H OCH3OCH3CH452″″″H OCH3CH3N453″OCH3″H OCH3OCH3CH454″″″H OCH3CH3N455″OHSO2CH3H OCH3OCH3CH456″″″H OCH3CH3N457″OCH3″H OCH3OCH3CH 146-148458″″″H OCH3CH3N459″OHSO2NHCH3H OCH3OCH3CH460″″″H OCH3CH3N461″OCH3″H OCH3OCH3CH 179-180462″″″H OCH3CH3N463″OHSO2N(CH3)2H OCH3OCH3CH464″″″H OCH3CH3N465″OCH3″H OCH3OCH3CH 179-180466″″″H OCH3CH3N467″C2H5CHO H OCH3OCH3CH 168-170468″″″H OCH3CH3N469″″COCH3H OCH3OCH3CH470″″″H OCH3CH3N471″″環(huán)丙基H OCH3OCH3CH472″″″H OCH3CH3N473″″COCH2Cl H OCH3OCH3CH474″″″H OCH3CH3N475″″COCF3H OCH3OCH3CH476″″″H OCH3CH3N477″″COOCH3H OCH3OCH3CH478″″″H OCH3CH3NVb.R1R4R5R7X Y Z Fp.℃479″ ″ COC6H5HOCH3OCH3CH480″ ″ ″HOCH3CH3N481″ ″ CONHC2H5HOCH3OCH3CH482″ ″ ″HOCH3CH3N483″ ″ CSNHC2H5HOCH3OCH3CH484″ ″ ″HOCH3CH3N485″ ″ SO2CH3HOCH3OCH3CH 154-155486″ ″ ″HOCH3CH3N487″ ″ SO2NHCH3HOCH3OCH3CH 150-152488″ ″ ″HOCH3CH3N489″ ″ SO2N(CH3)2HOCH3OCH3CH490″ ″ ″HOCH3CH3N491″ ″ SO2C6H5HOCH3OCH3CH492″ ″ ″HOCH3CH3N493CO2C2H5H CHO HOCH3OCH3CH494″ ″ ″HOCH3CH3N495″ ″ COCH3HOCH3OCH3CH496″ ″ ″HOCH3CH3N497″ ″ SO2CH3HOCH3OCH3CH498″ ″ ″HOCH3CH3N499″ CH3CHO HOCH3OCH3CH500″ ″ ″HOCH3CH3N501″ ″ COCH3HOCH3OCH3CH502″ ″ ″HOCH3CH3N503″ ″ SO2CH3HOCH3OCH3CH504″ ″ ″HOCH3CH3N505″ C2H5CHO HOCH3OCH3CH506″ ″ ″HOCH3CH3N507″ ″ COCH3HOCH3OCH3CH508″ ″ ″HOCH3CH3N509″ ″ SO2CH3HOCH3OCH3CH510″ ″ ″HOCH3CH3N511″ OH CHO HOCH3OCH3CH512″ ″ ″HOCH3CH3N513″ ″ COCH3HOCH3OCH3CHVb.R1R4R5R7XY Z Fp.℃514″″ ″ H OCH3CH3N515″ ″ SO2CH3H OCH3OCH3CH516″ ″ ″ H OCH3CH3N517″ OCH3CHO H OCH3OCH3CH518″ ″ ″ H OCH3CH3N519″ ″ COCH3H OCH3OCH3CH520″ ″ ″ H OCH3CH3N521CO2-n-BuH CHO H OCH3OCH3CH522CON(CH3)2CH3CHO H OCH3CH3N523CONHCH3H CHO H OCH3OCH3CH524COSCH3CH3COCH3H OCH3CH3N525CO2CH3n-BuCHOH OCH3OCH3CH526″ ″ ″ H OCH3CH3N527″ H ″ H OCH2CF3N(CH3)2N528″ CH3″ H ″ ″N529″ H COCH3H ″ ″″530″ CH3″ H ″ ″″531″ ″ SO2CH3H OCH3OCH3CH532″ ″ ″ H OCH3CH3N533CO2CH3 H OCH3OCH3CH534″ ″ H OCH3CH3N535CO2CH3CH3CHOH OCH3OCH3CH 鈉鹽236-238536CO2CH3H SO2CH3H OCH3OCH3CH 鈉鹽170-173537CO2CH3CH3SO2CH3H OCH3OCH3CH 鈉鹽191538CO2CH3OCH3CHOH OCH3OCH3CH 鈉鹽215-216539CO2CH3OCH3COCH3H OCH3OCH3CH 鈉鹽Vb.R1R4R5R7XY ZFp.℃540 CO2CH3H COOCH3H OCH3OCH3CH 鈉鹽203-205541 CO2CH3CH3SO2N(CH3)2H OCH3OCH3CH 鈉鹽122542 CO2CH3CH3CONHEt H OCH3OCH3CH 鈉鹽190-192543 CO2CH3CH3CONHEt H OCH3OCH3CH150-152544 CO2CH3CH3CONHEt H OCH3CH3N545 CO2CH3H CONHEt H OCH3OCH3CH546 CO2CH3H CONHEt H OCH3CH3N547 CO2CH3-CO-CH2CH2-CO- H OCH3OCH3CH220-221548 CO2CH3-CO-CH2CH2-CO- H OCH3OCH3N549 CO2CH3-CO-CH2CH2-CO- H OCH3CH3CH550 CO2CH3-CO-CH2CH2-CO- H OCH3CH3N551 CO2CH3-CO-CH2CH2-CO- H OCH3OCH3CH鈉鹽210-212552 CO2CH3OCH3COCF3H OCH3OCH3CH鈉鹽228-229553 CO2CH3OCH3COOCH3H OCH3OCH3CH鈉鹽184-185554 CO2CH3OCH3Cyclopropyl H OCH3OCH3CH鈉鹽216555 CO2CH3OCH3SO2CH3H OCH3OCH3CH 鈉鹽183-185556 CO2CH3C2H5CHO H OCH3OCH3CH鈉鹽237-239557 CO2CH3C2H5Cyclopropyl H OCH3OCH3CH鈉鹽178-180558 CO2CH3C2H5COCCl3H OCH3OCH3CH109-111559 CO2CH3C2H5COCCl3H OCH3OCH3CH鈉鹽174-176560 CO2CH3C2H5COCCl3H OCH3CH3N561 CO2CH3C2H5COCOOCH3H OCH3CH3N562 CO2CH3C2H5COCOOCH3H OCH3OCH3CH138-140563 CO2CH3C2H5COCH2OCH3H OCH3OCH3CH121-123Vb. R1R4R5R7X Y ZFp.℃564 CO2CH3C2H5COCH2OCH3H OCH3CH3N565 CO2CH3C2H5SO2CH3H OCH3OCH3CH 154-155566 CO2CH3C2H5SO2CH3H OCH3OCH3CH 鈉鹽161567 CO2CH3C2H5SO2NHCH3H OCH3OCH3CH 150-152568 CO2CH3C2H5SO2NHCH3H OCH3OCH3CH 鈉鹽165-168569 CO2CH3OC2H5SO2CH3H OCH3OCH3CH 163-164570 CO2CH3OC2H5SO2CH3H OCH3OCH3CH 鈉鹽166-168571 CO2CH3OC2H5CHO H OCH3OCH3CH 165-166572 CO2CH3OC2H5CHO H OCH3OCH3CH 鈉鹽207-208573 CO2CH3OCH3CONHPhH OCH3OCH3CH 178-179574 CO2CH3OCH3CONHEtH OCH3OCH3CH 155-157575 CO2CH3OCH3COCCl3H OCH3OCH3CH 165-168576 CO2CH3OCH3COCCl3H OCH3OCH3CH 鈉鹽100577 CO2CH3OCH3COCHCl2H OCH3OCH3CH 145-150578 CO2CH3OCH3COCHCl2H OCH3OCH3CH 鈉鹽235表2 Vb.R1R4R5R7X Y Z Fp.℃1 CO2CH3H CHO HOCH3OCH3CH 142-1442 ″″″HOCH3CH3CH3 ″″″HCH3CH3CH4 ″″″HCH3OC2H5CH5 ″″″HOCH3OCH3N6 ″″″HOCH3CH3N7 ″″″HOCH3Cl CH8 ″″″HOCF2H CH3CH9 ″″″HOCF2H OCF2H CH10″″″HOCH3Br CH11″″″HOCH3OC2H5CH12″″″HOCH3SCH3CH13″″″HOCH3OC2H5N14″″″HOCH3OC3H7CH15″″″HCH3Cl CH16″″″HCl OC2H5CH17″″″HOC2H5OC2H5CH18″″″HC2H5OCH3CH19″″″HCF3OCH3CH20″″″HOCH2CF3CH3CH21″″″HOCH2CF3OCH3CH22″″″HOCH2CF3OCH2CF3CH23″″″HOCH2CF3OCH3N24″″″HOCH3CH(OCH3)2CH25″″″CH3OCH3OCH3CHVb. R1R4R5R7X YZFp.℃26″″″ CH3OCH3CH3N27″H COCH3HOCH3OCH3CH 167-16928″″″ HOCH3CH3CH29″″″ HCH3CH3CH30″″″ HCH3OC2H5CH31″″″ HOCH3OCH3N32″″″ HOCH3CH3N33″″″ HOCH3Cl CH34″″″ HOCF2H CH3CH35″″″ HOCF2H OCF2H CH36″″″ HOCH3Br CH37″″″ HOCH3OC2H5CH38″″″ HOCH3SCH3CH39″″″ HOCH3OC2H5N40″″″ HOCH3OC3H7CH41″″″ HCH3Cl CH42″″″ HCl OC2H5CH43″″″ HOC2H5OC2H5CH44″″″ HC2H5OCH3CH45″″″ HCF3OCH3CH46″″″ HOCH2CF3CH3CH47″″″ HOCH2CF3OCH3CH48″″″ HOCH2CF3OCH2CF3CH49″″″ HOCH2CF3OCH3N50″″″ HOCH3 CH(OCH3)2CH51″″″ CH3OCH3OCH3CH52″″″ CH3OCH3CH3N53″CH3CHO HOCH3OCH3CH 160-16254″″″ HOCH3CH3CH55″″″ HCH3CH3CH56″″″ HCH3OC2H5CH57″″″ HOCH3OCH3N58″″″ HOCH3CH3N59″″″ HOCH3Cl CH60″″″ HOCF2H CH3CHVb. R1R4R5R7X Y ZFp.℃61″″″HOCF2HOCF2H CH62″″″HOCH3Br CH63″″″HOCH3OC2H5CH64″″″HOCH3SCH3CH65″″″HOCH3OC2H5N66″″″HOCH3OC3H7CH67″″″HCH3Cl CH68″″″HClOC2H5CH69″″″HOC2H5OC2H5CH70″″″HC2H5OCH3CH71″″″HCF3OCH3CH72″″″HOCH2CF3CH3CH73″″″HOCH2CF3OCH3CH74″″″HOCH2CF3OCH2CF3CH75″″″HOCH2CF3OCH3N76″″″HOCH3CH(OCH3)3CH77″″″CH3OCH3OCH3CH78″″″CH3OCH3CH3N79″CH3COCH3HOCH3OCH3CH 166-16880″″″HOCH3CH3CH81″″″HCH3CH3CH82″″″HCH3OC2H5CH83″″″HOCH3OCH3N84″″″HOCH3CH3N85″″″HOCH3Cl CH86″″″HOCF2HCH3CH87″″″HOCF2HOCF2H CH88″″″HOCH3Br CH89″″″HOCH3OC2H5CH90″″″HOCH3SCH3CH91″″″HOCH3OC2H5N92″″″HOCH3OC3H7CH93″″″HCH3Cl CH94″″″HClOC2H5CH95″″″HOC2H5OC2H5CHVb.R1R4R5R7X Y ZFp.℃96 ″″″ HC2H5OCH3CH97 ″″″ HCF3OCH3CH98 ″″″ HOCH2CF3CH3CH99 ″″″ HOCH2CF3OCH3CH100″″″ HOCH2CF3OCH2CF3CH101″″″ HOCH2CF3OCH3N102″″″ HOCH3CH(OCH3)2CH103″″″ CH3OCH3OCH3CH104″″″ CH3OCH3CH3N105″H SO2CH3HOCH3OCH3CH106″″″ HOCH3CH3CH107″″″ HCH3CH3CH108″″″ HOCH3OCH3N109″″″ HOCH3CH3N110″″″ HOC2H5NHCH3N111″″″ CH3OCH3OCH3CH112″″″ CH3OCH3CH3N113″CH3SO2CH3H OCH3OCH3CH114″″″ HOCH3CH3CH115″″″ HCH3CH3CH116″″″ HOCH3OCH3N117″″″ HOCH3CH3N118″″″ HOC2H5NHCH3N119″″″ CH3OCH3OCH3CH120″″″ CH3OCH3CH3N121″OHCHO HOCH3OCH3CH122″″″ HOCH3CH3CH123″″″ HCH3CH3CH124″″″ HOCH3OCH3N125″″″ HOCH3CH3N126″″″ HOC2H5NHCH3N127″″″ CH3OCH3OCH3CH128″″″ CH3OCH3CH3N129″OCH3CHO HOCH3OCH3CH130″″″ HOCH3CH3CHVb.R1R4R5R7XY ZFp.℃131″″″ HCH3CH3CH132″″″ HOCH3OCH3N133″″″ HOCH3CH3N134″″″ HOC2H5NHCH3N135″″″ CH3OCH3OCH3CH136″″″ CH3OCH3CH3N137″OHCOCH3HOCH3OCH3CH138″″″ HOCH3CH3CH139″″″ HCH3CH3CH140″″″ HOCH3OCH3N141″″″ HOCH3CH3N142″″″ HOC2H5NHCH3N143″″″ CH3OCH3OCH3CH144″″″ CH3OCH3CH3N145″OCH3COCH3HOCH3OCH3CH146″″″ HOCH3CH3CH147″″″ HCH3CH3CH148″″″ HOCH3OCH3N149″″″ HOCH3CH3N150″″″ HOC2H5NHCH3N151″″″ CH3OCH3OCH3CH152″″″ CH3OCH3CH3N153″H COC2H5HOCH3OCH3CH 196154″″″ HOCH3CH3CH155″″″ HOCH3OCH3N156″″″ HOCH3CH3N157″CH3″ HOCH3OCH3CH158″″″ HOCH3CH3CH159″″″ HOCH3OCH3N160″″″ HOCH3CH3N161″H COCH2OCH3HOCH3OCH3CH 192-195162″″″ HOCH3CH3CH163″″″ HOCH3OCH3N164″″″ HOCH3CH3N165″CH3″ HOCH3OCH3CHVb.R1R4R5R7X Y Z Fp.℃166″″″HOCH3CH3CH167″″″HOCH3OCH3N168″″″HOCH3CH3N169″H COCO2C2H5HOCH3OCH3CH 183-185170″″″HOCH3CH3CH171″″″HOCH3OCH3N172″″″HOCH3CH3N173″CH3″ HOCH3OCH3CH174″″″HOCH3CH3CH175″″″HOCH3OCH3N176″″″HOCH3CH3N177″H COCF3HOCH3OCH3CH 180-182178″″″HOCH3CH3CH179″″″HOCH3OCH3N180″″″HOCH3CH3N181″CH3″HOCH3OCH3CH 144-147182″″″HOCH3CH3CH183″″″HOCH3OCH3N184″″″HOCH3CH3N185″H COOCH3HOCH3OCH3CH 178-180186″″″HOCH3CH3CH187″″″HOCH3OCH3N188″″″HOCH3CH3N189″CH3″HOCH3OCH3CH190″″″HOCH3CH3CH191″″″HOCH3OCH3N192″″″HOCH3CH3N193″H CONHC2H5HOCH3OCH3CH194″″″HOCH3CH3CH195″″″HOCH3OCH3N196″″″HOCH3CH3N197″CH3″ HOCH3OCH3CH198″″″HOCH3CH3CH199″″″HOCH3OCH3N200″″″HOCH3CH3NVb.R1R4R5R7X Y ZFp.℃201″ HCSNHC2H5HOCH3OCH3CH202″ ″ ″ HOCH3CH3CH203″ ″ ″ HOCH3OCH3N204″ ″ ″ HOCH3CH3N205″ CH3″ HOCH3OCH3CH206″ ″ ″ HOCH3CH3CH207″ ″ ″ HOCH3OCH3N208″ ″ ″ HOCH3CH3N209″ HSO2NHCH3HOCH3OCH3CH210″ ″ ″ HOCH3CH3CH211″ ″ ″ HOCH3OCH3N212″ ″ ″ HOCH3CH3N213″ CH3″ HOCH3OCH3CH214″ ″ ″ HOCH3CH3CH215″ ″ ″ HOCH3OCH3N216″ ″ ″ HOCH3CH3N217″ HSO2N(CH3)2HOCH3OCH3CH218″ ″ ″ HOCH3CH3CH219″ ″ ″ HOCH3OCH3N220″ ″ ″ HOCH3CH3N221″ CH3″ HOCH3OCH3CH222″ ″ ″ HOCH3CH3CH223″ ″ ″ HOCH3OCH3N224″ ″ ″ HOCH3CH3N225″-CH2CH2CH2CO-HOCH3OCH3CH226″ ″ HOCH3CH3CH227″ ″ HOCH3OCH3N228″ ″ HOCH3CH3N229″-CH2CH2CH2SO2- HOCH3OCH3CH230″ ″ HOCH3CH3CH231″ ″ HOCH3OCH3N232″ ″ HOCH3CH3N233″-CH2CH2CH2CH2CO-HOCH3OCH3CH234″ ″ HOCH3CH3CH235″ ″ HOCH3OCH3NVb.R1R4R5R7X Y ZFp.℃236″ ″ HOCH3CH3N237″-CH2CH2CH2CH2SO2- HOCH3OCH3CH238″ ″ HOCH3CH3CH239″ ″ HOCH3OCH3N240″ ″ HOCH3CH3N241″-CH2CH2OCH2CH2-HOCH3OCH3CH242″ ″ HOCH3CH3CH243″ ″ HOCH3OCH3N244″ ″ HOCH3CH3N245″HCOC3H7HOCH3OCH3CH246″″ ″ HOCH3CH3CH247″″ ″ HOCH3OCH3N248″″ ″ HOCH3CH3N249″CH3″ HOCH3OCH3CH250″″ ″ HOCH3CH3CH251″″ ″ HOCH3OCH3N252″″ ″ HOCH3CH3N253″HCOCH2Cl HOCH3OCH3CH 170-172254″″ ″ HOCH3CH3CH255″″ ″ HOCH3OCH3N256″″ ″ HOCH3CH3N257″CH3″ HOCH3OCH3CH258″″ ″ HOCH3CH3CH259″″ ″ HOCH3OCH3N260″″ ″ HOCH3CH3N261″HCOCHCl2HOCH3OCH3CH 158-160262″″ ″ HOCH3CH3CH263″″ ″ HOCH3OCH3N264″″ ″ HOCH3CH3N265″CH3″ HOCH3OCH3CH266″″ ″ HOCH3CH3CH267″″ ″ HOCH3OCH3N268″″ ″ HOCH3CH3N269″HCOCCl3HOCH3OCH3CH 194-196270″″ ″ HOCH3CH3CHVb.R1R4R5R7XY ZFp.℃271″″″ HOCH3OCH3N272″″″ HOCH3CH3N273″CH3″ HOCH3OCH3CH274″″″ HOCH3CH3CH275″″″ HOCH3OCH3N276″″″ HOCH3CH3N277″H COCH＝CH2HOCH3OCH3CH278″″″ HOCH3CH3CH279″″″ HOCH3OCH3N280″″″ HOCH3CH3N281″CH3″ HOCH3OCH3CH282″″″ HOCH3CH3CH283″″″ HOCH3OCH3N284″″″ HOCH3CH3N285″H COC＝CH HOCH3OCH3CH286″″″ HOCH3CH3CH287″″″ HOCH3OCH3N288″″″ HOCH3CH3N289″CH3″ HOCH3OCH3CH290″″″ HOCH3CH3CH291″″″ HOCH3OCH3N292″″″ HOCH3CH3N293″H COC6H5HOCH3OCH3CH294″″″ HOCH3CH3CH295″″″ HOCH3OCH3N296″″″ HOCH3CH3N297″CH3″ HOCH3OCH3CH298″″″ HOCH3CH3CH299″″″ HOCH3OCH3N300″″″ HOCH3CH3N301″SO2C6H5SO2C6H5HOCH3OCH3CH302″″″ HOCH3CH3CH303″″″ HOCH3OCH3N304″″″ HOCH3CH3N305″SO2CH3SO2CH3HOCH3OCH3CHVb.R1R4R5R7X Y ZFp.℃306″″″HOCH3CH3CH307″″″HOCH3OCH3N308″″″HOCH3CH3N309″H COCH2Br HOCH3OCH3CH310″″″HOCH3CH3N311″CH3″HOCH3OCH3CH312″″″HOCH3CH3N313″H COCH2F HOCH3OCH3CH314″″″HOCH3CH3N315″CH3″HOCH3OCH3CH316″″″HOCH3CH3N317″H COCH2C＝CH HOCH3OCH3CH318″″″HOCH3CH3N319″CH3″HOCH3OCH3CH320″″″HOCH3CH3N321″H COCO2CH3HOCH3OCH3CH322″″″HOCH3CH3N323″CH3″HOCH3OCH3CH324″″″HOCH3CH3N325″H CO2C2H5HOCH3OCH3CH326″″″HOCH3CH3N327″CH3″HOCH3OCH3CH328″″″HOCH3CH3N329″H COSCH3HOCH3OCH3CH330″″″HOCH3CH3N331″CH3″HOCH3OCH3CH332″″″HOCH3CH3N333″H CSOCH3HOCH3OCH3CH334″″″HOCH3CH3N335″CH3″HOCH3OCH3CH336″″″HOCH3CH3N337″H CSSCH3HOCH3OCH3CH338″″″HOCH3CH3N339″CH3″HOCH3OCH3CH340″″″HOCH3CH3NVb. R1R4R5R7X Y Z Fp.℃341 ″H COCH(CH3)2H OCH3OCH3CH 195-196342 ″″″ H OCH3CH3N343 ″CH3″ H OCH3OCH3CH344 ″″″ H OCH3CH3N345 ″H COC(CH3)3H OCH3OCH3CH346 ″″″ H OCH3CH3N347 ″CH3″ H OCH3OCH3CH348 ″″″ H OCH3CH3N349 ″H CO-環(huán)丙基 H OCH3OCH3CH 202-203350 ″″″ H OCH3CH3N351 ″CH3″ H OCH3OCH3CH352 ″″″ H OCH3CH3N353 ″H CO-環(huán)丁基 H OCH3OCH3CH354 ″″″ H OCH3CH3N355 ″CH3″ H OCH3OCH3CH356 ″″″ H OCH3CH3N357 ″H CO-環(huán)戊基 H OCH3OCH3CH358 ″″″ H OCH3CH3N359 ″CH3″ H OCH3OCH3CH360 ″″″ H OCH3CH3N361 ″H CO-環(huán)己基 H OCH3OCH3CH362 ″″″ H OCH3CH3N363 ″CH3″ H OCH3OCH3CH364 ″″″ H OCH3CH3N365 ″H CONHCH2CH2Cl H OCH3OCH3CH 178-182366 ″″″ H OCH3CH3N367 ″CH3″ H OCH3OCH3CH368 ″″″ H OCH3CH3N369 ″H CSNHCH2CH2Cl H OCH3OCH3CH370 ″″″ H OCH3CH3N371 ″CH3″ H OCH3OCH3CH372 ″″″ H OCH3CH3N373 ″H CONH-n-C4H9H OCH3OCH3CH 183-184374 ″″″ H OCH3CH3N375 ″CH3″ H OCH3OCH3CHVb.R1R4R5R7X Y ZFp.℃376″″″HOCH3CH3N377″H CSNHCH3HOCH3OCH3CH378″″″HOCH3CH3N379″CH3″HOCH3OCH3CH380″″″HOCH3CH3N381″H CSNHCH2CH＝CH2HOCH3OCH3CH382″″″HOCH3CH3N383″CH3″HOCH3OCH3CH384″″″HOCH3CH3N385″CH3CSNHCH2COCH3HOCH3OCH3CH386″″″HOCH3CH3N387″CH3CSNHCH2COC2H5HOCH3OCH3CH388″″″HOCH3CH3N389″CH3CONHCH2COCH3HOCH3OCH3CH390″″″HOCH3CH3N391″CH3CONHCH2COC2H5HOCH3OCH3CH392″″″HOCH3CH3N393″-CONHCH2CO-HOCH3OCH3CH394″″″HOCH3CH3N395″H SO2CH2FHOCH3OCH3CH396″″″HOCH3CH3N397″CH3″HOCH3OCH3CH398″″″HOCH3CH3N399″H SO2CF3HOCH3OCH3CH400″″″HOCH3CH3N401″CH3″HOCH3OCH3CH402″″″HOCH3CH3N403″H SO2C2H5HOCH3OCH3CH404″″″HOCH3CH3N405″CH3″HOCH3OCH3CH406″″″HOCH3CH3N407″H SO2-n-C3H7HOCH3OCH3CH408″″″HOCH3CH3N409″CH3″HOCH3OCH3CH410″″″HOCH3CH3NVb R1R4R5R7X Y Z Fp.℃411″OHCOC2H5H OCH3OCH3CH412″″″ H OCH3CH3N413″OCH3″ H OCH3OCH3CH414″″″ H OCH3CH3N415″OHCOCH2Cl H OCH3OCH3CH416″″″ H OCH3CH3N417″OCH3″ H OCH3OCH3CH418″″″ H OCH3CH3N419″OHCOCF3H OCH3OCH3CH420″″″ H OCH3CH3N421″OCH3″ H OCH3OCH3CH422″″″ H OCH3CH3N423″OHCOCH2OCH3H OCH3OCH3CH424″″″ H OCH3CH3N425″OCH3″ H OCH3OCH3CH426″″″ H OCH3CH3N427″OHCOCO2C2H5H OCH3OCH3CH428″″″ H OCH3CH3N429″OCH3″ H OCH3OCH3CH430″″″ H OCH3CH3N431″OHCOOCH3H OCH3OCH3CH432″″″ H OCH3CH3N433″OCH3″ H OCH3OCH3CH434″″″ H OCH3CH3N435″OH環(huán)丙基 H OCH3OCH3CH436″″″ H OCH3CH3N437″OCH3″ H OCH3OCH3CH438″″″ H OCH3CH3N439″OHCOC6H5H OCH3OCH3CH440″″″ H OCH3CH3N441″OCH3″ H OCH3OCH3CH442″″″ H OCH3CH3N443″OHCOCH(CH3)2H OCH3OCH3CH444″″″ H OCH3CH3N445″OCH3″ H OCH3OCH3CHVb R1R4R5R7X Y ZFp.℃446″″″ HOCH3CH3N447″OHCOCH＝CH2HOCH3OCH3CH448″″″ HOCH3CH3N449″OCH3″ HOCH3OCH3CH450″″″ HOCH3CH3N451″OHCOC＝CH HOCH3OCH3CH452″″″ HOCH3CH3N453″OCH3″ HOCH3OCH3CH454″″″ HOCH3CH3N455″OHSO2CH3HOCH3OCH3CH456″″″ HOCH3CH3N457″OCH3″ HOCH3OCH3CH458″″″ HOCH3CH3N459″OHSO2NHCH3HOCH3OCH3CH460″″″ HOCH3CH3N461″OCH3″ HOCH3OCH3CH462″″″ HOCH3CH3N463″OHSO2N(CH3)2H OCH3OCH3CH464″″″ HOCH3CH3N465″OCH3″ HOCH3OCH3CH466″″″ HOCH3CH3N467″C2H5CHO HOCH3OCH3CH468″″″ HOCH3CH3N469″″COCH3HOCH3OCH3CH470″″″ HOCH3CH3N471″″環(huán)丙基 HOCH3OCH3CH472″″″ HOCH3CH3N473″″COCH2Cl HOCH3OCH3CH474″″″ HOCH3CH3N475″″COCF3HOCH3OCH3CH476″″″ HOCH3CH3N477″″COOCH3HOCH3OCH3CH478″″″ HOCH3CH3N479″″COC6H5HOCH3OCH3CH480″″″ HOCH3CH3NVb.R1R4R5R7X Y ZFp.℃481″ ″CONHC2H5HOCH3OCH3CH482″ ″″ HOCH3CH3N483″ ″CSNHC2H5HOCH3OCH3CH484″ ″″ HOCH3CH3N485″ ″SO2CH3HOCH3OCH3CH486″ ″″ HOCH3CH3N487″ ″SO2NHCH3HOCH3OCH3CH488″ ″″ HOCH3CH3N489″ ″SO2N(CH3)2HOCH3OCH3CH490″ ″″ HOCH3CH3N491″ ″SO2C6H5HOCH3OCH3CH492″ ″″ HOCH3CH3N493CO2C2H5H CHO HOCH3OCH3CH494″ ″″ HOCH3CH3N495″ ″COCH3HOCH3OCH3CH496″ ″″ HOCH3CH3N497″ ″SO2CH3HOCH3OCH3CH498″ ″″ HOCH3CH3N499″ CH3CHOHOCH3OCH3CH500″ ″″ HOCH3CH3N501″ ″COCH3HOCH3OCH3CH502″ ″″ HOCH3CH3N503″ ″SO2CH3HOCH3OCH3CH504″ ″″ HOCH3CH3N505″ C2H5CHO HOCH3OCH3CH506″ ″″ HOCH3CH3N507″ ″COCH3HOCH3OCH3CH508″ ″″ HOCH3CH3N509″ ″SO2CH3HOCH3OCH3CH510″ ″″ HOCH3CH3N511″ OHCHOHOCH3OCH3CH512″ ″″ HOCH3CH3N513″ ″COCH3HOCH3OCH3CH514″ ″″ HOCH3CH3N515″ ″SO2CH3HOCH3OCH3CHVb.R1R4R5R7XY ZFp.℃516″″″ HOCH3CH3N517″OCH3CHOHOCH3OCH3CH518″″″ HOCH3CH3N519″″COCH3HOCH3OCH3CH520″″″ HOCH3CH3N521CO2-n-Bu H CHOH″OMeCH522CONMe2Me″ H″Me N523CONHMeH ″ H″OMeCH524COSMe MeCO-Me H″Me N525CO2Men-Bu CHOH″OMeCH526″n-Bu ″ H″Me N527″H ″ HOCH2CF3NMe2″528″Me″ H″″ ″529″H CO-Me H″″ ″530″Me″ H″″ ″531″″SO2CH3HOCH3OCH3CH532″″″ HOCH3CH3N533″ HOCH3OCH3CH534″ ″ HOCH3CH3N
表3 VbR1R4R5R7XY ZFp.℃1CO2CH3HCHOHOCH3OCH3CH2″ ″″HOCH3CH3CH3″ ″″HCH3CH3CH4″ ″″HCH3OC2H5CH5″ ″″HOCH3OCH3N6″ ″″HOCH3CH3N7″ ″″HOCH3ClCH8″ ″″HOCF2HCH3CH9″ ″″HOCF2HOCF2HCH10 ″ ″″HOCH3BrCH11 ″ ″″HOCH3OC2H5CH12 ″ ″″HOCH3SCH3CH13 ″ ″″HOCH3OC2H5N14 ″ ″″HOCH3OC3H7CH15 ″ ″″HCH3Cl CH16 ″ ″″HClOC2H5CH17 ″ ″″HOC2H5OC2H5CH18 ″ ″″HC2H5OCH3CH19 ″ ″″HCF3OCH3CH20 ″ ″″HOCH2CF3CH3CH21 ″ ″″HOCH2CF3OCH3CH22 ″ ″″HOCH2CF3OCH2CF3CH23 ″ ″″HOCH2CF3OCH3N24 ″ ″″HOCH3CH(OCH3)2CHVb. R1R4R5R7X Y ZFp.℃25″″″CH3OCH3OCH3CH26″″″CH3OCH3CH3N27″H COCH3HOCH3OCH3CH 198-20028″″″HOCH3CH3CH29″″″HCH3CH3CH30″″″HCH3OC2H5CH31″″″HOCH3OCH3N32″″″HOCH3CH3N33″″″HOCH3Cl CH34″″″HOCF2HCH3CH35″″″HOCF2HOCF2H CH36″″″HOCH3Br CH37″″″HOCH3OC2H5CH38″″″HOCH3SCH3CH39″″″HOCH3OC2H5N40″″″HOCH3OC3H7CH41″″″HCH3Cl CH42″″″HClOC2H5CH43″″″HOC2H5OC2H5CH44″″″HC2H5OCH3CH45″″″HCF3OCH3CH46″″″HOCH2CF3CH3CH47″″″HOCH2CF3OCH3CH48″″″HOCH2CF3OCH2CF3CH49″″″HOCH2CF3OCH3N50″″″HOCH3CH(OCH3)2CH51″″″CH3OCH3OCH3CH52″″″CH3OCH3CH3N53″CH3CHO HOCH3OCH3CH54″″″HOCH3CH3CH55″″″HCH3CH3CH56″″″HCH3OC2H5CH57″″″HOCH3OCH3N58″″″HOCH3CH3N59″″″HOCH3Cl CHVb. R1R4R5R7X Y ZFp.℃60″″″HOCF2HCH3CH61″″″HOCF2HOCF2H CH62″″″HOCH3Br CH63″″″HOCH3OC2H5CH64″″″HOCH3SCH3CH65″″″HOCH3OC2H5N66″″″HOCH3OC3H7CH67″″″HCH3Cl CH68″″″HClOC2H5CH69″″″HOC2H5OC2H5CH70″″″HC2H5OCH3CH71″″″HCF3OCH3CH72″″″HOCH2CF3CH3CH73″″″HOCH2CF3OCH3CH74″″″HOCH2CF3OCH2CF3CH75″″″HOCH2CF3OCH3N76″″″HOCH3CH(OCH3)2CH77″″″CH3OCH3OCH3CH78″″″CH3OCH3CH3N79″CH3COCH3HOCH3OCH3CH80″″″HOCH3CH3CH81″″″HCH3CH3CH82″″″HCH3OC2H5CH83″″″HOCH3OCH3N84″″″HOCH3CH3N85″″″HOCH3Cl CH86″″″HOCF2HCH3CH87″″″HOCF2HOCF2H CH88″″″HOCH3Br CH89″″″HOCH3OC2H5CH90″″″HOCH3SCH3CH91″″″HOCH3OC2H5N92″″″HOCH3OC3H7CH93″″″HCH3Cl CH94″″″HClOC2H5CHVb R1R4R5R7X Y ZFp.℃95 ″″″ HOC2H5OC2H5CH96 ″″″ HC2H5OCH3CH97 ″″″ HCF3OCH3CH98 ″″″ HOCH2CF3CH3CH99 ″″″ HOCH2CF3OCH3CH100″″″ HOCH2CF3OCH2CF3CH101″″″ HOCH2CF3OCH3N102″″″ HOCH3CH(OCH3)2CH103″″″ CH3OCH3OCH3CH104″″″ CH3OCH3CH3N105″HSO2CH3HOCH3OCH3CH106″″″ HOCH3CH3CH107″″″ HCH3CH3CH108″″″ HOCH3OCH3N109″″″ HOCH3CH3N110″″″ HOC2H5NHCH3N111″″″ CH3OCH3OCH3CH112″″″ CH3OCH3CH3N113″CH3SO2CH3HOCH3OCH3CH114″″″ HOCH3CH3CH115″″″ HCH3CH3CH116″″″ HOCH3OCH3N117″″″ HOCH3CH3N118″″″ HOC2H5NHCH3N119″″″ CH3OCH3OCH3CH120″″″ CH3OCH3CH3N121″OHCHO HOCH3OCH3CH122″″″ HOCH3CH3CH123″″″ HCH3CH3CH124″″″ HOCH3OCH3N125″″″ HOCH3CH3N126″″″ HOC2H5NHCH3N127″″″ CH3OCH3OCH3CH128″″″ CH3OCH3CH3N129″OCH3CHO HOCH3OCH3CHVb.R1R4R5R7X Y ZFp.℃130″″″ HOCH3CH3CH131″″″ HCH3CH3CH132″″″ HOCH3OCH3N133″″″ HOCH3CH3N134″″″ HOC2H5NHCH3N135″″″ CH3OCH3OCH3CH136″″″ CH3OCH3CH3N137″OHCOCH3HOCH3OCH3CH138″″″ HOCH3CH3CH139″″″ HCH3CH3CH140″″″ HOCH3OCH3N141″″″ HOCH3CH3N142″″″ HOC2H5NHCH3N143″″″ CH3OCH3OCH3CH144″″″ CH3OCH3CH3N145″OCH3COCH3HOCH3OCH3CH146″″″ HOCH3CH3CH147″″″ HCH3CH3CH148″″″ HOCH3OCH3N149″″″ HOCH3CH3N150″″″ HOC2H5NHCH3N151″″″ CH3OCH3OCH3CH152″″″ CH3OCH3CH3N153″H COC2H5HOCH3OCH3CH154″″″ HOCH3CH3CH155″″″ HOCH3OCH3N156″″″ HOCH3CH3N157″CH3″ HOCH3OCH3CH158″″″ HOCH3CH3CH159″″″ HOCH3OCH3N160″″″ HOCH3CH3N161″H COCH2OCH3HOCH3OCH3CH162″″″ HOCH3CH3CH163″″″ HOCH3OCH3N164″″″ HOCH3CH3NVb.R1R4R5R7X Y ZFp.℃165″CH3″ HOCH3OCH3CH166″″″ HOCH3CH3CH167″″″ HOCH3OCH3N168″″″ HOCH3CH3N169″H COCO2C2H5H OCH3OCH3CH170″″″ HOCH3CH3CH171″″″ HOCH3OCH3N172″″″ HOCH3CH3N173″CH3″ HOCH3OCH3CH174″″″ HOCH3CH3CH175″″″ HOCH3OCH3N176″″″ HOCH3CH3N177″H COCF3HOCH3OCH3CH178″″″ HOCH3CH3CH179″″″ HOCH3OCH3N180″″″ HOCH3CH3N181″CH3″ HOCH3OCH3CH182″″″ HOCH3CH3CH183″″″ HOCH3OCH3N184″″″ HOCH3CH3N185″H COOCH3HOCH3OCH3CH186″″″ HOCH3CH3CH187″″″ HOCH3OCH3N188″″″ HOCH3CH3N189″CH3″ HOCH3OCH3CH190″″″ HOCH3CH3CH191″″″ HOCH3OCH3N192″″″ HOCH3CH3N193″HCONHC2H5HOCH3OCH3CH194″″″ HOCH3CH3CH195″″″ HOCH3OCH3N196″″″ HOCH3CH3N197″CH3″ HOCH3OCH3CH198″″″ HOCH3CH3CH199″″″ HOCH3OCH3NVb.R1R4R5R7X Y ZFp.℃200″″″ HOCH3CH3N201″H CSNHC2H5HOCH3OCH3CH202″″″ HOCH3CH3CH203″″″ HOCH3OCH3N204″″″ HOCH3CH3N205″CH3″ HOCH3OCH3CH206″″″ HOCH3CH3CH207″″″ HOCH3OCH3N208″″″ HOCH3CH3N209″H SO2NHCH3HOCH3OCH3CH210″″″ HOCH3CH3CH211″″″ HOCH3OCH3N212″″″ HOCH3CH3N213″CH3″ HOCH3OCH3CH214″″″ HOCH3CH3CH215″″″ HOCH3OCH3N216″″″ HOCH3CH3N217″H SO2N(CH3)2H OCH3OCH3CH218″″″ HOCH3CH3CH219″″″ HOCH3OCH3N220″″″ HOCH3CH3N221″CH3 ″ HOCH3OCH3CH222″″″ HOCH3CH3CH223″″″ HOCH3OCH3N224″″″ HOCH3CH3N225″ -CH2CH2CH2CO- HOCH3OCH3CH226″ ″HOCH3CH3CH227″ ″HOCH3OCH3N228″ ″HOCH3CH3N229″ -CH2CH2CH2SO2- HOCH3OCH3CH230″ ″HOCH3CH3CH231″ ″HOCH3OCH3N232″ ″HOCH3CH3N233″ -CH2CH2CH2CH2CO- HOCH3OCH3CH234″ ″HOCH3CH3CHVb.R1R4R5R7X Y ZFp.℃235″ ″ HOCH3OCH3N236″ ″ HOCH3CH3N237″-CH2CH2CH2CH2SO2-H OCH3OCH3CH238″ ″ HOCH3CH3CH239″ ″ HOCH3OCH3N240″ ″ HOCH3CH3N241″-CH2CH2OCH2CH2- HOCH3OCH3CH242″ ″ HOCH3CH3CH243″ ″ HOCH3OCH3N244″ ″ HOCH3CH3N245″H COC3H7HOCH3OCH3CH246″″″ HOCH3CH3CH247″″″ HOCH3OCH3N248″″″ HOCH3CH3N249″CH3″ HOCH3OCH3CH250″″″ HOCH3CH3CH251″″″ HOCH3OCH3N252″″″ HOCH3CH3N253″H COCH2ClHOCH3OCH3CH254″″″ HOCH3CH3CH255″″″ HOCH3OCH3N256″″″ HOCH3CH3N257″CH3″ HOCH3OCH3CH258″″″ HOCH3CH3CH259″″″ HOCH3OCH3N260″″″ HOCH3CH3N261″H COCHCl2HOCH3OCH3CH262″″″ HOCH3CH3CH263″″″ HOCH3OCH3N264″″″ HOCH3CH3N265″CH3″ HOCH3OCH3CH266″″″ HOCH3CH3CH267″″″ HOCH3OCH3N268″″″ HOCH3CH3N269″H COCCl3HOCH3OCH3CHVb.R1R4R5R7X Y ZFp.℃270″″ ″ HOCH3CH3CH271″″ ″ HOCH3OCH3N272″″ ″ HOCH3CH3N273″CH3″ HOCH3OCH3CH274″″ ″ HOCH3CH3CH275″″ ″ HOCH3OCH3N276″″ ″ HOCH3CH3N277″H COCH＝CH2HOCH3OCH3CH278″″ ″ HOCH3CH3CH279″″ ″ HOCH3OCH3N280″″ ″ HOCH3CH3N281″CH3″ HOCH3OCH3CH282″″ ″ HOCH3CH3CH283″″ ″ HOCH3OCH3N284″″ ″ HOCH3CH3N285″H COC＝CH HOCH3OCH3CH286″″ ″ HOCH3CH3CH287″″ ″ HOCH3OCH3N288″″ ″ HOCH3CH3N289″CH3″ HOCH3OCH3CH290″″ ″ HOCH3CH3CH291″″ ″ HOCH3OCH3N292″″ ″ HOCH3CH3N293″H COC6H5HOCH3OCH3CH294″″ ″ HOCH3CH3CH295″″ ″ HOCH3OCH3N296″″ ″ HOCH3CH3N297″CH3″ HOCH3OCH3CH298″″ ″ HOCH3CH3CH299″″ ″ HOCH3OCH3N300″″ ″ HOCH3CH3N301″SO2C6H5SO2C6H5HOCH3OCH3CH302″″ ″ HOCH3CH3CH303″″ ″ HOCH3OCH3N304″″ ″ HOCH3CH3NVb.R1R4R5R7X Y ZFp.℃305″SO2CH3SO2CH3HOCH3OCH3CH306″″ ″ HOCH3CH3CH307″″ ″ HOCH3OCH3N308″″ ″ HOCH3CH3N309″HCOCH2BrHOCH3OCH3CH310″″ ″ HOCH3CH3N311″CH3″ HOCH3OCH3CH312″″ ″ HOCH3CH3N313″HCOCH2F HOCH3OCH3CH314″″ ″ HOCH3CH3N315″CH3″ HOCH3OCH3CH316″″ ″ HOCH3CH3N317″HCOCH2C＝CH HOCH3OCH3CH318″″ ″ HOCH3CH3N319″CH3″ HOCH3OCH3CH320″″ ″ HOCH3CH3N321″HCOCO2CH3HOCH3OCH3CH322″″ ″ HOCH3CH3N323″CH3″ HOCH3OCH3CH324″″ ″ HOCH3CH3N325″HCO2C2H5HOCH3OCH3CH326″″ ″ HOCH3CH3N327″CH3″ HOCH3OCH3CH328″″ ″ HOCH3CH3N329″HCOSCH3HOCH3OCH3CH330″″ ″ HOCH3CH3N331″CH3″ HOCH3OCH3CH332″″ ″ HOCH3CH3N333″HCSOCH3HOCH3OCH3CH334″″ ″ HOCH3CH3N335″CH3″ HOCH3OCH3CH336″″ ″ HOCH3CH3N337″HCSSCH3HOCH3OCH3CH338″″ ″ HOCH3CH3N339″CH3″ HOCH3OCH3CHVb. R1R4R5R7X Y ZFp.℃340 ″″″ HOCH3CH3N341 ″H COCH(CH3)2HOCH3OCH3CH342 ″″″ HOCH3CH3N343 ″CH3″ HOCH3OCH3CH344 ″″″ HOCH3CH3N345 ″H COC(CH3)3HOCH3OCH3CH346 ″″″ HOCH3CH3N347 ″CH3″ HOCH3OCH3CH348 ″″″ HOCH3CH3N349 ″H CO-環(huán)丙基 HOCH3OCH3CH350 ″″″ HOCH3CH3N351 ″CH3″ HOCH3OCH3CH352 ″″″ HOCH3CH3N353 ″H CO-環(huán)丁基 HOCH3OCH3CH354 ″″″ HOCH3CH3N355 ″CH3″ HOCH3OCH3CH356 ″″″ HOCH3CH3N357 ″H CO-環(huán)戊基 HOCH3OCH3CH358 ″″″ HOCH3CH3N359 ″CH3″ HOCH3OCH3CH360 ″″″ HOCH3CH3N361 ″H CO-環(huán)己基 HOCH3OCH3CH362 ″″″ HOCH3CH3N363 ″CH3″ HOCH3OCH3CH364 ″″″ HOCH3CH3N365 ″H CONHCH2CH2ClHOCH3OCH3CH366 ″″″ HOCH3CH3N367 ″CH3″ HOCH3OCH3CH36B ″″″ HOCH3CH3N369 ″H CSNHCH2CH2ClHOCH3OCH3CH370 ″″″ HOCH3CH3N371 ″CH3″ HOCH3OCH3CH372 ″″″ HOCH3CH3N373 ″H CONH-n-C4H9HOCH3OCH3CH374 ″″″ HOCH3CH3NVb.R1R4R5R7X Y ZFp.℃375″CH3″ HOCH3OCH3CH376″″″ HOCH3CH3N377″H CSNHCH3HOCH3OCH3CH378″″″ HOCH3CH3N379″CH3″ HOCH3OCH3CH380″″″ HOCH3CH3N381″H CSNHCH2CH＝CH2HOCH3OCH3CH382″″″ HOCH3CH3N383″CH3″ HOCH3OCH3CH384″″″ HOCH3CH3N385″CH3CSNHCH2COCH3HOCH3OCH3CH386″″″ HOCH3CH3N387″CH3CSNHCH2COC2H5HOCH3OCH3CH388″″″ HOCH3CH3N389″CH3CONHCH2COCH3HOCH3OCH3CH390″″″ HOCH3CH3N391″CH3CONHCH2COC2H5HOCH3OCH3CH392″″″ HOCH3CH3N393″-CONHCH2CO- HOCH3OCH3CH394″″ HOCH3CH3N395″H SO2CH2F HOCH3OCH3CH396″″″ HOCH3CH3N397″CH3″ HOCH3OCH3CH398″″″ HOCH3CH3N399″H SO2CF3HOCH3OCH3CH400″″″ HOCH3CH3N401″CH3″ HOCH3OCH3CH402″″″ HOCH3CH3N403″H SO2C2H5HOCH3OCH3CH404″″″ HOCH3CH3N405″CH3″ HOCH3OCH3CH406″″″ HOCH3CH3N407″H SO2-n-C3H7HOCH3OCH3CH408″″″ HOCH3CH3N409″CH3″ HOCH3OCH3CHVb.R1R4R5R7X Y ZFp.℃410″″ ″HOCH3CH3N411″OH COC2H5HOCH3OCH3CH412″″ ″HOCH3CH3N413″OCH3″HOCH3OCH3CH414″″ ″HOCH3CH3N415″OH COCH2Cl HOCH3OCH3CH416″″ ″HOCH3CH3N417″OCH3″HOCH3OCH3CH418″″ ″HOCH3CH3N419″OH COCF3HOCH3OCH3CH420″″ ″HOCH3CH3N421″OCH3″HOCH3OCH3CH422″″ ″HOCH3CH3N423″OH COCH2OCH3HOCH3OCH3CH424″″ ″HOCH3CH3N425″OCH3″HOCH3OCH3CH426″″ ″HOCH3CH3N427″OH COCO2C2H5HOCH3OCH3CH428″″ ″HOCH3CH3N429″OCH3″HOCH3OCH3CH430″″ ″HOCH3CH3N431″OH COOCH3HOCH3OCH3CH432″″ ″HOCH3CH3N433″OCH3″HOCH3OCH3CH434″″ ″HOCH3CH3N435″OH 環(huán)丙基HOCH3OCH3CH436″″ ″HOCH3CH3N437″OCH3″HOCH3OCH3CH438″″ ″HOCH3CH3N439″OH COC6H5HOCH3OCH3CH440″″ ″HOCH3CH3N441″OCH3″HOCH3OCH3CH442″″ ″HOCH3CH3N443″OH COCH(CH3)2HOCH3OCH3CH444″″ ″HOCH3CH3NVb.R1R4R5R7X Y Z Fp.℃445″OCH3″H OCH3OCH3CH446″″″H OCH3CH3N447″OHCOCH＝CH2H OCH3OCH3CH448″″″H OCH3CH3N449″OCH3″H OCH3OCH3CH450″″″H OCH3CH3N451″OHCOC＝CH H OCH3OCH3CH452″″″H OCH3CH3N453″OCH3″H OCH3OCH3CH454 ″″H OCH3CH3N455″OHSO2CH3H OCH3OCH3CH456″″″H OCH3CH3N457″OCH3″H OCH3OCH3CH458″″″H OCH3CH3N459″OHSO2NHCH3H OCH3OCH3CH460″″″H OCH3CH3N461″OCH3″H OCH3OCH3CH462″″″H OCH3CH3N463″OHSO3N(CH3)2H OCH3OCH3CH464″″″H OCH3CH3N465″OCH3″H OCH3OCH3CH466″″″H OCH3CH3N467″C2H5CHO H OCH3OCH3CH468″″″H OCH3CH3N469″″COCH3H OCH3OCH3CH470″″″H OCH3CH3N471″″環(huán)丙基H OCH3OCH3CH472″″″H OCH3CH3N473″″COCH2Cl H OCH3OCH3CH474″″″H OCH3CH3N475″″COCF3H OCH3OCH3CH476″″″H OCH3CH3N477″″COOCH3H OCH3OCH3CH478″″″H OCH3CH3N479″″COC6H5H OCH3OCH3CHVb. R1R4R5R7X Y Z Fp.℃480″″″HOCH3CH3N481″″CONHC2H5HOCH3OCH3CH482″″″HOCH3CH3N483″″CSNHC2H5HOCH3OCH3CH484″″″HOCH3CH3N485″″SO2CH3HOCH3OCH3CH486″″″HOCH3CH3N487″″SO2NHCH3HOCH3OCH3CH488″″″HOCH3CH3N489″″SO2N(CH3)2HOCH3OCH3CH490″″″HOCH3CH3N491″″SO2C6H5HOCH3OCH3CH492″″″HOCH3CH3N493CO2C2H5HCHO HOCH3OCH3CH494″″″HOCH3CH3N495″″COCH3HOCH3OCH3CH496″″″HOCH3CH3N497″″SO2CH3HOCH3OCH3CH498″″″HOCH3CH3N499″CH3CHO HOCH3OCH3CH500″″″HOCH3CH3N501″″COCH3HOCH3OCH3CH502″″″HOCH3CH3N503″″SO2CH3HOCH3OCH3CH504″″″HOCH3CH3N505″C2H5CHOHOCH3OCH3CH506″″″HOCH3CH3N507″″COCH3HOCH3OCH3CH508″″″HOCH3CH3N509″″SO2CH3HOCH3OCH3CH510″″″HOCH3CH3N511″OHCHO HOCH3OCH3CH512″″″HOCH3CH3N513″″COCH3HOCH3OCH3CH514″″″HOCH3CH3NVb.R1R4R5R7X Y Z Fp.℃515″″ SO2CH3HOCH3OCH3CH516″″ ″ HOCH3CH3N517″OCH3CHO HOCH3OCH3CH518″″ ″ HOCH3CH3N519″″ COCH3HOCH3OCH3CH520″″ ″ HOCH3CH3N521COO-n-Bu H CHO H″ OMe CH522CONMe2Me ″ H″ Me N523CONHMeH ″ H″ OMe CH524COSMe Me CO-Me H″ Me N525COOMe n-Bu CHO H″ OMe CH526″″ ″ H″ Me N527″H ″ HOCH2CF3NMe2N528″Me ″ H″ ″ N529″H CO-Me H″ ″ N530″Me ″ H″ ″ N531″″ SO2CH3HOCH3OCH3CH532″″ ″ HOCH3CH3N533″ HOCH3OCH3CH534″ ″ HOCH3CH3N535CO2CH3H COCH3HOCH3OCH3CH Na-Salz270
表4 Vb. R1R4R5R7X Y ZFp.℃1CO2CH3H CHO HOCH3OCH3CH2″ ″″HOCH3CH3CH3″ ″″HCH3CH3CH4″ ″″HCH3OC2H5CH5″ ″″HOCH3OCH3N6″ ″″HOCH3CH3N7″ ″″HOCH3Cl CH8″ ″″HOCF2HCH3CH9″ ″″HOCF2HOCF2H CH10 ″ ″″HOCH3Br CH11 ″ ″″HOCH3OC2H5CH12 ″ ″″HOCH3SCH3CH13 ″ ″″HOCH3OC2H5N14 ″ ″″HOCH3OC3H7CH15 ″ ″″HCH3Cl CH16 ″ ″″HClOC2H5CH17 ″ ″″HOC2H5OC2H5CH18 ″ ″″HC2H5OCH3CH19 ″ ″″HCF3OCH3CH20 ″ ″″HOCH2CF3CH3CH21 ″ ″″HOCH2CF3OCH3CH22 ″ ″″HOCH2CF3OCH2CF3CH23 ″ ″″HOCH2CF3OCH3N24 ″ ″″HOCH3CH(OCH3)2CHVb. R1R4R5R7X YZFp.℃25″″″ CH3OCH3OCH3CH26″″″ CH3OCH3CH3N27″H COCH3HOCH3OCH3CH28″″″ HOCH3CH3CH29″″″ HCH3CH3CH30″″″ HCH3OC2H5CH31″″″ HOCH3OCH3N32″″″ HOCH3CH3N33″″″ HOCH3Cl CH34″″″ HOCF2HCH3CH35″″″ HOCF2HOCF2H CH36″″″ HOCH3Br CH37″″″ HOCH3OC2H5CH38″″″ HOCH3SCH3CH39″″″ HOCH3OC2H5N40″″″ HOCH3OC3H7CH41″″″ HCH3Cl CH42″″″ HClOC2H5CH43″″″ HOC2H5OC2H5CH44″″″ HC2H5OCH3CH45″″″ HCF3OCH3CH46″″″ HOCH2CF3CH3CH47″″″ HOCH2CF3OCH3CH48″″″ HOCH2CF3OCH2CF3CH49″″″ HOCH2CF3OCH3N50″″″ HOCH3CH(OCH3)2CH51″″″ CH3OCH3OCH3CH52″″″ CH3OCH3CH3N53″CH3CHO HOCH3OCH3CH 150-15154″″″ HOCH3CH3CH55″″″ HCH3CH3CH56″″″ HCH3OC2H5CH57″″″ HOCH3OCH3N58″″″ HOCH3CH3N59″″″ HOCH3Cl CHVb. R1R4R5R7X Y ZFp.℃60″″″HOCF2HCH3CH61″″″HOCF2HOCF2H CH62″″″HOCH3Br CH63″″″HOCH3OC2H5CH64″″″HOCH3SCH3CH65″″″HOCH3OC2H5N66″″″HOCH3OC3H7CH67″″″HCH3Cl CH68″″″HClOC2H5CH69″″″HOC2H5OC2H5CH70″″″HC2H5OCH3CH71″″″HCF3OCH3CH72″″″HOCH2CF3CH3CH73″″″HOCH2CF3OCH3CH74″″″HOCH2CF3OCH2CF3CH75″″″HOCH2CF3OCH3N76″″″HOCH3CH(OCH3)2CH77″″″CH3OCH3OCH3CH78″″″CH3OCH3CH3N79″CH3COCH3HOCH3OCH3CH80″″″HOCH3CH3CH81″″″HCH3CH3CH82″″″HCH3OC2H5CH83″″″HOCH3OCH3N84″″″HOCH3CH3N85″″″HOCH3Cl CH86″″″HOCF2HCH3CH87″″″HOCF2HOCF2H CH88″″″HOCH3Br CH89″″″HOCH3OC2H5CH90″″″HOCH3SCH3CH91″″″HOCH3OC2H5N92″″″HOCH3OC3H7CH93″″″HCH3Cl CH94″″″HClOC2H5CHVb.R1R4R5R7X Y Z Fp.℃95 ″″″ HOC2H5OC2H5CH96 ″″″ HC2H5OCH3CH97 ″″″ HCF3OCH3CH98 ″″″ HOCH2CF3CH3CH99 ″″″ HOCH2CF3OCH3CH100″″″ HOCH2CF3OCH2CF3CH101″″″ HOCH2CF3OCH3N102″″″ HOCH3CH(OCH3)2CH103″″″ CH3OCH3OCH3CH104″″″ CH3OCH3CH3N105″H SO2CH3HOCH3OCH3CH106″″″ HOCH3CH3CH107″″″ HCH3CH3CH108″″″ HOCH3OCH3N109″″″ HOCH3CH3N110″″″ HOC2H5NHCH3N111″″″ CH3OCH3OCH3CH112″″″ CH3OCH3CH3N113″CH3SO2CH3HOCH3OCH3CH114″″″ HOCH3CH3CH115″″″ HCH3CH3CH116″″″ HOCH3OCH3N117″″″ HOCH3CH3N118″″″ HOC2H5NHCH3N119″″″ CH3OCH3OCH3CH120″″″ CH3OCH3CH3N121″OHCHO HOCH3OCH3CH122″″″ HOCH3CH3CH123″″″ HCH3CH3CH124″″″ HOCH3OCH3N125″″″ HOCH3CH3N126″″″ HOC2H5NHCH3N127″″″ CH3OCH3OCH3CH128″″″ CH3OCH3CH3N129″OCH3CHO HOCH3OCH3CHVb.R1R4R5R7X Y Z Fp.℃130″″″ HOCH3CH3CH131″″″ HCH3CH3CH132″″″ HOCH3OCH3N133″″″ HOCH3CH3N134″″″ HOC2H5NHCH3N135″″″ CH3OCH3OCH3CH136″″″ CH3OCH3CH3N137″OHCOCH3HOCH3OCH3CH138″″″ HOCH3CH3CH139″″″ HCH3CH3CH140″″″ HOCH3OCH3N141″″″ HOCH3CH3N142″″″ HOC2H5NHCH3N143″″″ CH3OCH3OCH3CH144″″″ CH3OCH3CH3N145″OCH3COCH3HOCH3OCH3CH146″″″ HOCH3CH3CH147″″″ HCH3CH3CH148″″″ HOCH3OCH3N149″″″ HOCH3CH3N150″″″ HOC2H5NHCH3N151″″″ CH3OCH3OCH3CH152″″″ CH3OCH3CH3N153″H COC2H5HOCH3OCH3CH154″″″ HOCH3CH3CH155″″″ HOCH3OCH3N156″″″ HOCH3CH3N157″CH3″ HOCH3OCH3CH158″″″ HOCH3CH3CH159″″″ HOCH3OCH3N160″″″ HOCH3CH3N161″H COCH2OCH3H OCH3OCH3CH162″″″ HOCH3CH3CH163″″″ HOCH3OCH3N164″″″ HOCH3CH3NVb.R1R4R5R7X Y Z Fp.℃165″CH3″ HOCH3OCH3CH166″″″ HOCH3CH3CH167″″″ HOCH3OCH3N168″″″ HOCH3CH3N169″H COCO2C2H5HOCH3OCH3CH170″″″ HOCH3CH3CH171″″″ HOCH3OCH3N172″″″ HOCH3CH3N173″CH3″ HOCH3OCH3CH174″″″ HOCH3CH3CH175″″″ HOCH3OCH3N176″″″ HOCH3CH3N177″H COCF3HOCH3OCH3CH178″″″ HOCH3CH3CH179″″″ HOCH3OCH3N180″″″ HOCH3CH3N181″CH3″ HOCH3OCH3CH182″″″ HOCH3CH3CH183″″″ HOCH3OCH3N184″″″ HOCH3CH3N185″H COOCH3HOCH3OCH3CH186″″″ HOCH3CH3CH187″″″ HOCH3OCH3N188″″″ HOCH3CH3N189″CH3″ HOCH3OCH3CH190″″″ HOCH3CH3CH191″″″ HOCH3OCH3N192″″″ HOCH3CH3N193″H CONHC2H5HOCH3OCH3CH194″″″ HOCH3CH3CH195″″″ HOCH3OCH3N196″″″ HOCH3CH3N197″CH3″ HOCH3OCH3CH198″″″ HOCH3CH3CH199″″″ HOCH3OCH3NVb.R1R4R5R7X Y Z Fp.℃200″″″HOCH3CH3N201″H CSNHC2H5HOCH3OCH3CH202″″″HOCH3CH3CH203″″″HOCH3OCH3N204″″″HOCH3CH3N205″CH3″HOCH3OCH3CH206″″″HOCH3CH3CH207″″″HOCH3OCH3N208″″″HOCH3CH3N209″H SO2NHCH3HOCH3OCH3CH210″″″HOCH3CH3CH211″″″HOCH3OCH3N212″″″HOCH3CH3N213″CH3″HOCH3OCH3CH214″″″HOCH3CH3CH215″″″HOCH3OCH3N216″″″HOCH3CH3N217″H SO2N(CH3)2HOCH3OCH3CH218″″″HOCH3CH3CH219″″″HOCH3OCH3N220″″″HOCH3CH3N221″CH3″HOCH3OCH3CH222″″″HOCH3CH3CH223″″″HOCH3OCH3N224″″″HOCH3CH3N225″-CH2CH2CH2CO- HOCH3OCH3CH226″ ″HOCH3CH3CH227″ ″HOCH3OCH3N228″ ″HOCH3CH3N229″-CH2CH2CH2SO2- HOCH3OCH3CH230″ ″HOCH3CH3CH231″ ″HOCH3OCH3N232″ ″HOCH3CH3N233″-CH2CH2CH2CH2CO- HOCH3OCH3CH234″ ″H CH3CH3CHVb.R1R4R5R7X Y Z Fp.℃235″ ″ HOCH3OCH3N236″ ″ HOCH3CH3N237″-CH2CH2CH2CH2SO2-H OCH3OCH3CH238″ ″ HOCH3CH3CH239″ ″ HOCH3OCH3N240″ ″ HOCH3CH3N241″-CH2CH2OCH2CH2- HOCH3OCH3CH242″ ″ HOCH3CH3CH243″ ″ HOCH3OCH3N244″ ″ HOCH3CH3N245″H COC3H7HOCH3OCH3CH246″″″ HOCH3CH3CH247″″″ HOCH3OCH3N248″″″ HOCH3CH3N249″CH3″ HOCH3OCH3CH250″″″ HOCH3CH3CH251″″″ HOCH3OCH3N252″″″ HOCH3CH3N253″H COCH2Cl HOCH3OCH3CH254″″″ HOCH3CH3CH255″″″ HOCH3OCH3N256″″″ HOCH3CH3N257″CH3″ HOCH3OCH3CH258″″″ HOCH3CH3CH259″″″ HOCH3OCH3N260″″″ HOCH3CH3N261″H COCHCl2HOCH3OCH3CH262″″″ HOCH3CH3CH263″″″ HOCH3OCH3N264″″″ HOCH3CH3N265″CH3″ HOCH3OCH3CH266″″″ HOCH3CH3CH267″″″ HOCH3OCH3N268″″″ HOCH3CH3N269″H COCCl3HOCH3OCH3CHVb R1R4R5R7X Y ZFp℃270″″ ″ HOCH3CH3CH271″″ ″ HOCH3OCH3N272″″ ″ HOCH3CH3N273″CH3″ HOCH3OCH3CH274″″ ″ HOCH3CH3CH275″″ ″ HOCH3OCH3N276″″ ″ HOCH3CH3N277″H COCH＝CH2HOCH3OCH3CH278″″ ″ HOCH3CH3CH279″″ ″ HOCH3OCH3N280″″ ″ HOCH3CH3N281″CH3″ HOCH3OCH3CH282″″ ″ HOCH3CH3CH283″″ ″ HOCH3OCH3N284″″ ″ HOCH3CH3N285″H COC＝CHHOCH3OCH3CH286″″ ″ HOCH3CH3CH287″″ ″ HOCH3OCH3N288″″ ″ HOCH3CH3N289″CH3″ HOCH3OCH3CH290″″ ″ HOCH3CH3CH291″″ ″ HOCH3OCH3N292″″ ″ HOCH3CH3N293″H COC6H5HOCH3OCH3CH294″″ ″ HOCH3CH3CH295″″ ″ HOCH3OCH3N296″″ ″ HOCH3CH3N297″CH3″ HOCH3OCH3CH298″″ ″ HOCH3CH3CH299″″ ″ HOCH3OCH3N300″″ ″ HOCH3CH3N301″SO2C6H5SO2C6H5H OCH3OCH3CH302″″ ″ HOCH3CH3CH303″″ ″ HOCH3OCH3N304″″ ″ HOCH3CH3NVbR1R4R5R7X Y Z Fp.℃305″SO2CH3SO2CH3HOCH3OCH3CH306″″″HOCH3CH3CH307″″″HOCH3OCH3N308″″″HOCH3CH3N309″H COCH2Br HOCH3OCH3CH310″″″HOCH3CH3N311″CH3″HOCH3OCH3CH312″″″HOCH3CH3N313″H COCH2F HOCH3OCH3CH314″″″HOCH3CH3N315″CH3″HOCH3OCH3CH316″″″HOCH3CH3N317″H COCH2C＝CH HOCH3OCH3CH318″″″HOCH3CH3N319″CH3″HOCH3OCH3CH320″″″HOCH3CH3N321″H COCO2CH3HOCH3OCH3CH322″″″HOCH3CH3N323″CH3″HOCH3OCH3CH324″″″HOCH3CH3N325″H CO2C2H5HOCH3OCH3CH326″″″HOCH3CH3N327″CH3″HOCH3OCH3CH328″″″HOCH3CH3N329″H COSCH3HOCH3OCH3CH330″″″HOCH3CH3N331″CH3″HOCH3OCH3CH332″″″HOCH3CH3N333″H CSOCH3HOCH3OCH3CH334″″″HOCH3CH3N335″CH3″HOCH3OCH3CH336″″″HOCH3CH3N337″H CSSCH3HOCH3OCH3CH338″″″HOCH3CH3N339″CH3″HOCH3OCH3CHVb.R1R4R5R7X Y Z Fp.℃340″″″ HOCH3CH3N341″H COCH(CH3)2HOCH3OCH3CH342″″″ HOCH3CH3N343″CH3″ HOCH3OCH3CH344″″″ HOCH3CH3N345″H COC(CH3)3HOCH3OCH3CH346″″″ HOCH3CH3N347″CH3″ HOCH3OCH3CH348″″″ HOCH3CH3N349″H CO-環(huán)丙基 HOCH3OCH3CH350″″″ HOCH3CH3N351″CH3″ HOCH3OCH3CH352″″″ HOCH3CH3N353″H CO-環(huán)丁基 HOCH3OCH3CH354″″″ HOCH3CH3N355″CH3″ HOCH3OCH3CH356″″″ HOCH3CH3N357″H CO-環(huán)戊基 HOCH3OCH3CH358″″″ HOCH3CH3N359″CH3″ HOCH3OCH3CH360″″″ HOCH3CH3N361″H CO-環(huán)己基 HOCH3OCH3CH362″″″ HOCH3CH3N363″CH3″ HOCH3OCH3CH364″″″ HOCH3CH3N365″H CONHCH2CH2ClHOCH3OCH3CH366″″″ HOCH3CH3N367″CH3″ HOCH3OCH3CH368″″″ HOCH3CH3N369″H CSNHCH2CH2ClHOCH3OCH3CH370″″″ HOCH3CH3N371″CH3″ HOCH3OCH3CH372″″″ HOCH3CH3N373″H CONH-n-C4H9HOCH3OCH3CH374″″″ HOCH3CH3NVb.R1R4R5R7XY ZFp.℃375″CH3″ HOCH3OCH3CH376″″ ″ HOCH3CH3N377″HCSNHCH3HOCH3OCH3CH378″″ ″ HOCH3CH3N379″CH3″ HOCH3OCH3CH380″″ ″ HOCH3CH3N381″HCSNHCH2CH＝CH2HOCH3OCH3CH382″″ ″ HOCH3CH3N383″CH3″ HOCH3OCH3CH384″″ ″ HOCH3CH3N385″CH3CSNHCH2COCH3HOCH3OCH3CH386″″ ″ HOCH3CH3N387″CH3CSNHCH2COC2H5HOCH3OCH3CH388″″ ″ HOCH3CH3N389″CH3CONHCH2COCH3HOCH3OCH3CH390″″ ″ HOCH3CH3N391″CH3CONHCH2COC2H5HOCH3OCH3CH392″″ ″ HOCH3CH3N393″-CONHCH2CO- HOCH3OCH3CH394″″HOCH3CH3N395″HSO2CH2F HOCH3OCH3CH396″″ ″ HOCH3CH3N397″CH3″ HOCH3OCH3CH398″″ ″ HOCH3CH3N399″HSO2CF3HOCH3OCH3CH400″″ ″ HOCH3CH3N401″CH3″ HOCH3OCH3CH402″″ ″ HOCH3CH3N403″HSO2C2H5HOCH3OCH3CH404″″ ″ HOCH3CH3N405″CH3″ HOCH3OCH3CH406″″ ″ HOCH3CH3N407″HSO2-n-C3H7HOCH3OCH3CH408″″ ″ HOCH3CH3N409″CH3″ HOCH3OCH3CHVb.R1R4R5R7X Y ZFp℃410 ″″H OCH3CH3N411″OHCOC2H5H OCH3OCH3CH412″″″H OCH3CH3N413″OCH3″H OCH3OCH3CH414″″″H OCH3CH3N415″OHCOCH2Cl H OCH3OCH3CH416″″″H OCH3CH3N417″OCH3″H OCH3OCH3CH418″″″H OCH3CH3N419″OHCOCF3H OCH3OCH3CH420″″″H OCH3CH3N421″OCH3″H OCH3OCH3CH422″″″H OCH3CH3N423″OHCOCH2OCH3H OCH3OCH3CH424″″″H OCH3CH3N425″OCH3″H OCH3OCH3CH426″″″H OCH3CH3N427″OHCOCO2C2H5H OCH3OCH3CH428″″″H OCH3CH3N429″OCH3″H OCH3OCH3CH430″″″H OCH3CH3N431″OHCOOCH3H OCH3OCH3CH432″″″H OCH3CH3N433″OCH3″H OCH3OCH3CH434″″″H OCH3CH3N435″OH環(huán)丙基H OCH3OCH3CH436″″″H OCH3CH3N437″OCH3″H OCH3OCH3CH438″″″H OCH3CH3N439″OHCOC6H5H OCH3OCH3CH440″″″H OCH3CH3N441″OCH3″H OCH3OCH3CH442″″″H OCH3CH3N443″OHCOCH(CH3)2H OCH3OCH3CH444″″″H OCH3CH3NVb. R1R4R5R7X Y Z Fp.℃445 ″OCH3″ H OCH3OCH3CH446 ″″″ H OCH3CH3N447 ″OHCOCH＝CH2H OCH3OCH3CH448 ″″″ H OCH3CH3N449 ″OCH3″ H OCH3OCH3CH450 ″″″ H OCH3CH3N451 ″OHCOCH＝CH H OCH3OCH3CH452 ″″″ H OCH3CH3N453 ″OCH3″ H OCH3OCH3CH454 ″″″ H OCH3CH3N455 ″OHSO2CH3H OCH3OCH3CH456 ″″″ H OCH3CH3N457 ″OCH3″ H OCH3OCH3CH458 ″″″ H OCH3CH3N459 ″OHSO2NHCH3H OCH3OCH3CH460 ″″″ H OCH3CH3N461 ″OCH3″ H OCH3OCH3CH462 ″″″ H OCH3CH3N463 ″OHSO2N(CH3)2H OCH3OCH3CH464 ″″″ H OCH3CH3N465 ″OCH3″ H OCH3OCH3CH466 ″″″ H OCH3CH3N467 ″C2H5CHO H OCH3OCH3CH468 ″″″ H OCH3CH3N469 ″″COCH3H OCH3OCH3CH470 ″″″ H OCH3CH3N471 ″″環(huán)丙基 H OCH3OCH3CH472 ″″″ H OCH3CH3N473 ″″COCH2Cl H OCH3OCH3CH474 ″″″ H OCH3CH3N475 ″″COCF3H OCH3OCH3CH476 ″″″ H OCH3CH3N477 ″″COOCH3H OCH3OCH3CH478 ″″″ H OCH3CH3N479 ″″COC6H5H OCH3OCH3CHVb R1R4R5R7X Y ZFp℃480″ ″″HOCH3CH3N481″ ″CONHC2H5HOCH3OCH3CH482″ ″″HOCH3CH3N483″ ″CSNHC2H5HOCH3OCH3CH484″ ″″HOCH3CH3N485″ ″SO2CH3HOCH3OCH3CH486″ ″″HOCH3CH3N487″ ″SO2NHCH3HOCH3OCH3CH488″ ″″HOCH3CH3N489″ ″SO2N(CH3)2HOCH3OCH3CH490″ ″″HOCH3CH3N491″ ″SO2C6H5HOCH3OCH3CH492″ ″″HOCH3CH3N493CO2C2H5H CHO HOCH3OCH3CH494″ ″″HOCH3CH3N495″ ″COCH3HOCH3OCH3CH496″ ″″HOCH3CH3N497″ ″SO2CH3HOCH3OCH3CH498″ ″″HOCH3CH3N499″ CH3CHO HOCH3OCH3CH500″ ″″HOCH3CH3N501″ ″COCH3HOCH3OCH3CH502″ ″″HOCH3CH3N503″ ″SO2CH3HOCH3OCH3CH504″ ″″HOCH3CH3N505″ C2H5CHO HOCH3OCH3CH506″ ″″HOCH3CH3N507″ ″COCH3HOCH3OCH3CH508″ ″″HOCH3CH3N509″ ″SO2CH3HOCH3OCH3CH510″ ″″HOCH3CH3N511″ OHCHO HOCH3OCH3CH512″ ″″HOCH3CH3N513″ ″COCH3HOCH3OCH3CH514″ ″″HOCH3CH3NVb R1R4R5R7X Y ZFp℃515″″SO2CH3HOCH3OCH3CH516″″″ HOCH3CH3N517″OCH3CHO HOCH3OCH3CH518″″″ HOCH3CH3N519″″COCH3HOCH3OCH3CH520″″″ HOCH3CH3N521COO-n-Bu H CHO H″ OMeCH522CONMe2Me″ H″ Me N523CONHMeH ″ H″ OMeCH524CO-SMeMeCO-MeH″ Me N525CO-OMen-Bu CHO H″ OMeCH526″n-Bu ″ H″ Me N527″H ″ HOCH2CF3NMe2N528″Me″ H″ ″ N529″H CO-MeH″ ″ N530″Me″ H″ ″ N531″″SO2CH3HOCH3OCH3CH532″″″ HOCH3CH3N533CO2CH3 HOCH3OCH3CH534″ ″HOCH3CH3N
B.制劑實(shí)施例a)粉劑的制備是通過(guò)混合10重量份的式(I)化合物和90重量份惰性物質(zhì)滑石并在錘磨中磨碎混合物。b)容易分散在水中的可濕性粉劑的制備是通過(guò)混合25重量份的式(I)化合物，64重量份惰性物質(zhì)含高嶺土石英，10重量份木質(zhì)素磺酸鉀和1重量份油?；谆；撬徕c作為濕潤(rùn)劑和分散劑，并在釘盤(pán)磨研磨混合物。c)容易分散在水中的濃懸浮液的制備是通過(guò)混合20重量份的式(I)化合物和6重量份的烷基酚聚乙二醇醚(riton X 207)，3重量份的異十三烷醇聚乙二醇醚(8EO)和71重量份石蠟礦物油(沸點(diǎn)范圍例如大約255至277℃)，并在球磨中研磨混合物至細(xì)度小于5微米。d)可乳化濃縮液的制備是通過(guò)混合15重量份的式(I)化合物，75重量份的環(huán)己烷溶劑和10重量份乙氧基化的壬基酚乳化劑。e)水分散顆粒劑的制備是通過(guò)混合75重量份 式(I)化合物10重量份 木質(zhì)素磺酸鈣5重量份十二烷基硫酸鈉3重量份聚乙烯醇和7重量份高嶺土，在針盤(pán)磨(stiftmhle)中研磨混合物并通過(guò)噴入作為成粒流體的水于流動(dòng)床上形成顆粒粉末。f)水分散性顆粒劑的制備還可通過(guò)在膠體磨中的勻化和預(yù)粉碎25重量份的式(I)化合物，5重量份2，2’-二萘基甲烷-6，6’-二磺酸鈉2重量份牛酰基甲基?；撬徕c(oleoylmethyltaurinsaures Natrium)1重量份聚乙烯醇17重量份碳酸鈣和50重量份水，然后在珠磨中研磨混合物用單物質(zhì)-噴嘴在噴霧塔中將所得懸浮液霧化，并干燥產(chǎn)品。C.生物實(shí)施例1.對(duì)雜草的苗前作用將單子葉和雙子葉雜草品種的種子或根莖放置于塑料盆中的沙質(zhì)沃土中并用土蓋上。然后將根據(jù)本發(fā)明式(I)化合物或其鹽作為可濕性粉劑或乳化濃縮液的水懸浮液或乳液，以600至800l水/ha的施用劑量，按不同劑量施用到覆蓋土的表面。
處理后，將盆放置在溫室中并保持雜草生長(zhǎng)的良好條件。試驗(yàn)期3至4周后，在供試植物萌發(fā)后，與未處理對(duì)照物比較，目測(cè)評(píng)價(jià)對(duì)植物的損害和對(duì)萌發(fā)的損害。如試驗(yàn)結(jié)果所示，根據(jù)本發(fā)明化合物對(duì)廣譜的禾本科雜草和雙子葉雜草具有好的苗前除草活性。例如表1中實(shí)施例1，27，53至55，58，59，79，105，113，129，145，153，177，181，185，189，213，217，221，253，257，421，425，429，433，437，445，457，461，465，467，485，487，535，至543，547，551至559，562，563，和565至578和表2中實(shí)施例1，27，53，79，153，161，169，177，181，185，253，261，269，341，349，365和373和表3中的實(shí)施例27和535和表4中的實(shí)施例53的化合物，以每公頃0.3Kg至0.005Kg活性物質(zhì)的劑量施用，對(duì)有害植物如田白芥、繁縷、珍珠菊和多花黑麥草具有好的苗前作用。2.對(duì)雜草的苗后作用將單子葉和雙子葉雜草品種的種子或根莖放置于塑料盆中的沙質(zhì)沃土中并用土蓋上并使之在良好條件的溫室中生長(zhǎng)。播種3周后，處理三葉期的的植物。將根據(jù)本發(fā)明式(I)化合物或其鹽作為可濕性粉劑或乳化濃縮液劑以不同的劑量，以600至800l水/ha施用劑量，施用到植物的綠色部分，其后在理想的生長(zhǎng)條件下，將供試植物放置在溫室中大約3至4周，與未處理對(duì)照物比較，目測(cè)評(píng)價(jià)制劑的活性。根據(jù)本發(fā)明制劑還對(duì)經(jīng)濟(jì)上重要的廣譜的禾本科雜草和雙子葉雜草具有好的苗后除草活性。例如表1中實(shí)施例1，27，53至55，58，59，79，105，113，129，145，153，177，181，185，189，213，217，221，253，257，421，425，429，433，437，445，457，461，465，467，485，487，535，至543，547，551至559，562，563，和565至578和表2中實(shí)施例1，27，53，79，153，161，169，177，181，185，253，261，269，341，349，365和373和表3中的實(shí)施例27和535和表4中的實(shí)施例53的化合物，以每公頃0.3Kg至0.005Kg活性物質(zhì)的劑量施用，對(duì)有害植物如田白芥、繁縷、珍珠菊和多花黑麥草具有好的苗后作用。3.作物的耐藥性在進(jìn)一步的溫室試驗(yàn)中，將許多種作物和雜草的種子放置于砂質(zhì)沃土中并用土覆蓋。
按照1.中所述方法立即處理一些盆，并把其余盆放在溫室中直到植物發(fā)育出二至三個(gè)真葉，然后如2.所述用不同劑量的根據(jù)本發(fā)明的式(I)化合物或其鹽進(jìn)行噴霧。
施藥并放置在溫室中四至五周后進(jìn)行目測(cè)評(píng)價(jià)，結(jié)果顯示甚至在高活性物質(zhì)使用劑量下，根據(jù)本發(fā)明化合物在苗前-和苗后-使用對(duì)雙子葉作物不會(huì)造成任何傷害，雙子葉作物如大豆、棉花、油菜、糖甜菜和土豆。而且，一些物質(zhì)甚至對(duì)禾本科作物無(wú)害，禾本科作物如大麥、小麥、黑麥、高粱、小米、玉米或水稻。因此，式(I)化合物或其鹽在防治農(nóng)作物中有害植物生長(zhǎng)時(shí)具有高度的選擇性。
權(quán)利要求
1.式(I)的化合物或其鹽， 其中R1為CO-Q-R8，R2和R3各自獨(dú)立為H或(C1-C4)烷基，R4為H，未取代或被一或多個(gè)下組包括的基團(tuán)取代的(C1-C8)烷基，上述取代基團(tuán)由鹵素、(C1-C4)烷氧基、(C1-C4)烷硫基、(C1-C4)烷基亞磺?；?、(C1-C4)烷基磺?；(C1-C4)烷氧基]羰基和CN組成，或?yàn)槲幢蝗〈虮灰恢炼鄠€(gè)鹵原子取代的(C3-C6)鏈烯基，或?yàn)槲幢蝗〈虮灰恢炼鄠€(gè)鹵原子取代的(C3-C6)鏈炔基，或?yàn)榱u基，(C1-C4)烷氧基，[(C1-C4)烷基]羰基或(C1-C4)烷基磺?；?，后三個(gè)基團(tuán)各自未被取代或在烷基部分被-或多個(gè)鹵原子或被(C1-C4)烷氧基或(C1-C4)烷硫基取代，或?yàn)楸交酋；?，其中苯基是未被取代或取代的，R5為(C1-C4)烷基磺?；?C3-C6)鏈烯基磺酰基，后兩個(gè)基團(tuán)各自未被取代或被一至多個(gè)鹵原子或被(C1-C4)烷氧基或(C1-C4)烷硫基取代的，或?yàn)楸交酋；虮交驶?，后兩個(gè)基團(tuán)的苯基各自未被取代或被取代，或?yàn)閱?或二-[(C1-C4)烷基]氨基磺?；騕(C1-C6)烷基]羰基，后三個(gè)基團(tuán)各自未被取代或被一或多個(gè)下述基團(tuán)取代，上述取代基由鹵素、(C1-C4)烷氧基、(C1-C4)烷硫基、(C1-C4)烷基亞磺?；?、(C1-C4)烷基磺酰基、[(C1-C4)烷基]羰基、[(C1-C4)烷氧基]羰基和CN組成，或?yàn)榧柞；?CO-CO-R’的基團(tuán)其中R’＝H，OH，(C1-C4)烷氧基或(C1-C4)烷基，或?yàn)閇(C3-C6)環(huán)烷基]羰基，[(C2-C6)鏈烯基]羰基或[(C2-C6)鏈炔基]羰基，后三個(gè)基團(tuán)各自未被取代或被一或多個(gè)鹵原子取代，或?yàn)橄率降幕鶊F(tuán) 或R4和R5一起為是(-CH2)mB-或-B1-(CH2)ml-B-，上述鏈?zhǔn)俏幢蝗〈虮灰粋€(gè)或多個(gè)(C1-C3)烷基取代和m為3或4或m1為2或3，和W為氧或硫原子，B和B1各自獨(dú)立為SO2或CO，Q為O，S或-NR13-，T為O或S，R6為H，(C1-C4)烷基，(C1-C4)烷氧基，[(C1-C4)烷基]羰基或[(C1-C4)烷氧基]羰基，后四個(gè)基團(tuán)各自未被取代或在烷基部分被一至多個(gè)鹵原子取代，或?yàn)辂u素，NO2或CN，R7為H或CH3，R8為H，(C1-C4)烷基，(C3-C4)鏈烯基或(C3-C4)鏈炔基，后三個(gè)基團(tuán)各自未被取代或被一或多個(gè)選自由鹵素、(C1-C4)烷氧基、(C1-C4)烷硫基、[(C1-C4)烷基]羰基和[(C1-C4)烷氧基]羰基組成的一組基團(tuán)取代，R9為(C1-C4)烷基，(C3-C4)鏈烯基或(C3-C4)鏈炔基，后三個(gè)基團(tuán)各自未被取代或被一或多個(gè)選自由鹵素、(C1-C4)烷氧基、(C1-C4)烷硫基、[(C1-C4)烷基]羰基和[(C1-C4)烷氧基]羰基組成的一組基團(tuán)取代，R10和R11各自獨(dú)立地為H，(C1-C4)烷基，(C3-C4)鏈烯基或(C3-C4)鏈炔基，后三個(gè)基團(tuán)各自未被取代或被一或多個(gè)由鹵素、(C1-C4)烷氧基、(C1-C4)烷硫基、[(C1-C4)烷基]羰基和[(C1-C4)烷氧基]羰基組成的一組基團(tuán)取代，R12基團(tuán)與氮原子一起為5或6元雜環(huán)，上述雜環(huán)在可能的氧化態(tài)中可含有一個(gè)其它N，O和S雜原子，且是未被取代或被(C1-C4)烷基或氧基取代，或被苯環(huán)稠和，R13為H，(C1-C4)烷基，(C3-C4)鏈烯基或(C3-C4)鏈炔基，后三個(gè)基團(tuán)各自未被取代或被一或多個(gè)由鹵素、(C1-C4)烷氧基、(C1-C4)烷硫基組成的一組基團(tuán)取代，A為下式的基團(tuán) X和Y基團(tuán)之一是氫，鹵素，(C1-C3)烷基或(C1-C3)烷氧基，后兩個(gè)基團(tuán)是未被取代或被鹵素單取代或多取代或被(C1-C3)烷氧基單取代，和X和Y基團(tuán)的另一個(gè)是氫，(C1-C3)烷基，(C1-C3)烷氧基或(C1-C3)烷硫基，后三個(gè)含有烷基的基團(tuán)是未被取代或被鹵原子單或多取代或被(C1-C3)烷氧基或(C1-C3)烷硫基單取代或二取代，或?yàn)槭絅R14R15的基團(tuán)，(C3-C6)環(huán)烷基，(C2-C4)鏈烯基，(C2-C4)鏈炔基，(C3-C4)鏈烯氧基，(C3-C4)鏈炔氧基，Z為CH或N，R14和R15各自彼此獨(dú)立地為H，(C1-C3)烷基，(C3-C4)鏈烯基，X1為CH3、OCH3、OC2H5或OCHF2，Y1為-O-或-CH2-X2為CH3、C2H5或CH2CF3Y2為OCH3、OC2H5、SCH3、SCH2CH3、CH3或C2H5X3為CH3或OCH3，Y3為H或CH3，X4為CH3、OCH3、OC2H5、CH2OCH3或Cl，Y4為CH3、OCH3、OC2H5或Cl和Y5為CH3、C2H5、OCH3或Cl。
2.根據(jù)權(quán)利要求1的化合物及其鹽，其中R4為H，未取代或被一或多個(gè)下組包括的基團(tuán)取代的(C1-C4)烷基，上述取代基團(tuán)由鹵素、(C1-C4)烷氧基、(C1-C4)烷硫基、(C1-C4)烷基磺?；(C1-C4)烷氧基]羰基和CN組成，或?yàn)?C3-C4)鏈烯基、(C3-C4)鏈炔基、羥基，(C1-C4)烷氧基，[(C1-C4)烷基]羰基或(C1-C4)烷基磺?；笪鍌€(gè)基團(tuán)各自未被取代或在烷基部分被一至多個(gè)鹵原子取代，或?yàn)楸交酋；?，其中苯基是未被取代或被一或多個(gè)下述基團(tuán)取代的，取代基由鹵素、(C1-C4)烷基和(C1-C4)烷氧基組成，和R5為(C1-C4)烷基磺?；?、(C1-C4)鹵代烷基磺?；?、苯基磺?；虮交驶?，后兩個(gè)基團(tuán)中的苯基各自未被取代或被一至多個(gè)選自鹵原子、(C1-C4)烷基和(C1-C4)烷氧基的基團(tuán)取代，或?yàn)閱?或二-[(C1-C4)烷基]氨基磺?；?，未被取代或被一或多個(gè)鹵原子或(C1-C4)烷氧基或(C1-C4)烷硫基取代的[(C1-C6)烷基]羰基，或?yàn)榧柞；?、OHC-CO-、2-氧-(C3-C5)鏈烷?；(C1-C4)烷氧基]草?；?、[(C3-C6)環(huán)烷基]羰基，[(C2-C4)鏈烯基]羰基或[(C2-C4)鏈炔基]羰基、或?yàn)橄率降幕鶊F(tuán) W為O或SR6為H、(C1-C4)烷基、(C1-C4)鹵代烷基、(C1-C4)烷氧基、(C1-C4)鹵代烷氧基或鹵素，R8各自為未被取代或被一或多個(gè)鹵原子取代的(C1-C4)烷基，或?yàn)?C3-C4)鏈烯基或(C3-C4)鏈炔基，R9為H、未被取代或被一或多個(gè)鹵原子或被(C1-C4)烷氧基、(C1-C4)烷硫基、[(C1-C4)烷氧基]羰基和[(C1-C4)烷基]羰基取代的(C1-C4)烷基，R10和R11各自獨(dú)立地為H、未被取代或被一或多個(gè)鹵原子取代的(C1-C4)烷基、或?yàn)?C3-C4)鏈烯基或(C3-C4)鏈炔基、其中R10和R11至少一個(gè)不是氫，R12基團(tuán)與氮原子一起為5或6元雜環(huán)，上述雜環(huán)在不同的氧化態(tài)中可含有一個(gè)其它N，O和S雜原子，且是未被取代或被(C1-C4)烷基或氧基取代，R13為H，未被取代或被一或多個(gè)由鹵素原子取代的(C1-C4)烷基、或?yàn)?C3-C4)鏈烯基或(C3-C4)鏈炔基。
3.根據(jù)權(quán)利要求1或2的化合物及其鹽，其中R4為H、(C1-C4)烷基、羥基或(C1-C4)烷氧基，R5為(C1-C4)烷基磺?；?、CHO、未被取代或被一或多個(gè)鹵原子取代的[(C1-C4)烷基]羰基、或?yàn)閇(C1-C4)烷氧基]草?；(C3-C6)環(huán)烷基]羰基或下式的基團(tuán) 其中W，T和R9至R12如上面式(I)中的定義，R6為H、(C1-C3)烷基、(C1-C3)烷氧基或鹵素，A為下式的基團(tuán) Z為CH或N，和X和Y基團(tuán)之一為鹵素、(C1-C2)烷基、(C1-C2)烷氧基、OCF2H、CF3或OCH2CF3和X和Y的另一個(gè)為(C1-C2)烷基、(C1-C2)烷氧基或(C1-C2)鹵代烷氧基。
4.根據(jù)權(quán)利要求1的式(I)化合物或其鹽的制備方法，其中包括a)式(II)的化合物與式(III)雜環(huán)氨基甲酸酯反應(yīng) R*-O-CO-NR7-A(III)其中R*是必要時(shí)被取代的苯基或(C1-C4)烷基，或b)式(IV)的苯基磺酰基氨基甲酸酯與式(V)的氨基雜環(huán)反應(yīng) H-NR7-A(V)或c)式(VI)的磺?；惽杷狨ヅc式(V)H-NR7-A的氨基雜環(huán)反應(yīng) 或d)在一個(gè)單釜反應(yīng)中，首先在堿存在下使式(V)H-NR7-A的氨基雜環(huán)化物與光氣反應(yīng)，然后反應(yīng)的中間體與式(II)的苯基磺酰胺反應(yīng)，或e)在堿存在下式(VII)的磺酰氯與其中M＝NH4、Na或K的氰酸酯M-OCN以及式(V)H-NR7-A的氨基雜環(huán)化物反應(yīng)， f)在堿存在下上述式(II)的磺酰胺與式(V’)的(硫代)異氰酸酯反應(yīng)W＝C＝N-A(V’)，在式(II)-(VII)和(V’)中的基團(tuán)R1-R7、A或W如在式(I)中的定義，在方法a)-e)中，最初獲得的是W＝O的式(I)化合物。
5.一種除草和植物生長(zhǎng)調(diào)節(jié)劑組合物，其中包含至少一種根據(jù)權(quán)利要求1至3的式(I)化合物或其鹽和植物保護(hù)中常用的制劑助劑。
6.一種防治有害植物或調(diào)節(jié)植物生長(zhǎng)的方法，其中包含施用有效量的至少一種根據(jù)權(quán)利要求1至3的式(I)化合物或其鹽于有害植物或植物、其植物種子或其生長(zhǎng)地。
7.根據(jù)權(quán)利要求1至3的式(I)化合物或其鹽作為除草劑或植物生長(zhǎng)調(diào)節(jié)劑的用途。
8.式(II)化合物 其中R1至R6如權(quán)利要求1中式(I)的定義。
9.根據(jù)權(quán)利要求8的式(II)化合物的制備方法，其中包含采用類(lèi)似于已知的方法使式(XV)化合物反應(yīng)以除去叔丁基保護(hù)基 式(XV)中R1至R6如式(II)中的定義。
全文摘要
權(quán)利要求1中定義的式(I)化合物及其鹽適合作為選擇性除草劑，見(jiàn)式(1)，其中R
文檔編號(hào)C07D417/12GK1135211SQ94194137
公開(kāi)日1996年11月6日 申請(qǐng)日期1994年10月12日 優(yōu)先權(quán)日1993年10月15日
發(fā)明者K·勞倫茲, L·威爾姆斯, K·保爾, H·比倫格 申請(qǐng)人:赫徹斯特-舍林農(nóng)業(yè)發(fā)展有限公司