CN1332604A - 手性咪唑类杀真菌组合物以及它们的使用方法 - Google Patents
手性咪唑类杀真菌组合物以及它们的使用方法 Download PDFInfo
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- CN1332604A CN1332604A CN99815247A CN99815247A CN1332604A CN 1332604 A CN1332604 A CN 1332604A CN 99815247 A CN99815247 A CN 99815247A CN 99815247 A CN99815247 A CN 99815247A CN 1332604 A CN1332604 A CN 1332604A
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- AWZOLILCOUMRDG-UHFFFAOYSA-N edifenphos Chemical compound C=1C=CC=CC=1SP(=O)(OCC)SC1=CC=CC=C1 AWZOLILCOUMRDG-UHFFFAOYSA-N 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
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- UZCGKGPEKUCDTF-UHFFFAOYSA-N fluazinam Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1NC1=NC=C(C(F)(F)F)C=C1Cl UZCGKGPEKUCDTF-UHFFFAOYSA-N 0.000 description 1
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- FQKUGOMFVDPBIZ-UHFFFAOYSA-N flusilazole Chemical compound C=1C=C(F)C=CC=1[Si](C=1C=CC(F)=CC=1)(C)CN1C=NC=N1 FQKUGOMFVDPBIZ-UHFFFAOYSA-N 0.000 description 1
- PTCGDEVVHUXTMP-UHFFFAOYSA-N flutolanil Chemical compound CC(C)OC1=CC=CC(NC(=O)C=2C(=CC=CC=2)C(F)(F)F)=C1 PTCGDEVVHUXTMP-UHFFFAOYSA-N 0.000 description 1
- HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical compound C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 description 1
- VUERQRKTYBIULR-UHFFFAOYSA-N fosetyl Chemical compound CCOP(O)=O VUERQRKTYBIULR-UHFFFAOYSA-N 0.000 description 1
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- UYJUZNLFJAWNEZ-UHFFFAOYSA-N fuberidazole Chemical compound C1=COC(C=2NC3=CC=CC=C3N=2)=C1 UYJUZNLFJAWNEZ-UHFFFAOYSA-N 0.000 description 1
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- 239000008103 glucose Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
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- 239000010440 gypsum Substances 0.000 description 1
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- 230000002363 herbicidal effect Effects 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
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- 229910052740 iodine Inorganic materials 0.000 description 1
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- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- WPOOICLZIIBUBM-UHFFFAOYSA-H iron;iron(3+);methyl-dioxido-oxo-$l^{5}-arsane Chemical compound [Fe].[Fe+3].[Fe+3].C[As]([O-])([O-])=O.C[As]([O-])([O-])=O.C[As]([O-])([O-])=O WPOOICLZIIBUBM-UHFFFAOYSA-H 0.000 description 1
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- UFHLMYOGRXOCSL-UHFFFAOYSA-N isoprothiolane Chemical compound CC(C)OC(=O)C(C(=O)OC(C)C)=C1SCCS1 UFHLMYOGRXOCSL-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- ZOTBXTZVPHCKPN-HTXNQAPBSA-N kresoxim-methyl Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=CC=C1C ZOTBXTZVPHCKPN-HTXNQAPBSA-N 0.000 description 1
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- 239000006210 lotion Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 1
- 229920000940 maneb Polymers 0.000 description 1
- 238000013507 mapping Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- CIFWZNRJIBNXRE-UHFFFAOYSA-N mepanipyrim Chemical compound CC#CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 CIFWZNRJIBNXRE-UHFFFAOYSA-N 0.000 description 1
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- CIEXPHRYOLIQQD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-2-furoylalaninate Chemical compound CC=1C=CC=C(C)C=1N(C(C)C(=O)OC)C(=O)C1=CC=CO1 CIEXPHRYOLIQQD-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 230000002371 mycocidal effect Effects 0.000 description 1
- BLCKKNLGFULNRC-UHFFFAOYSA-L n,n-dimethylcarbamodithioate;nickel(2+) Chemical compound [Ni+2].CN(C)C([S-])=S.CN(C)C([S-])=S BLCKKNLGFULNRC-UHFFFAOYSA-L 0.000 description 1
- HZDIJTXDRLNTIS-DAXSKMNVSA-N n-[[(z)-but-2-enoxy]methyl]-2-chloro-n-(2,6-diethylphenyl)acetamide Chemical compound CCC1=CC=CC(CC)=C1N(COC\C=C/C)C(=O)CCl HZDIJTXDRLNTIS-DAXSKMNVSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- OGYFATSSENRIKG-UHFFFAOYSA-N pencycuron Chemical compound C1=CC(Cl)=CC=C1CN(C(=O)NC=1C=CC=CC=1)C1CCCC1 OGYFATSSENRIKG-UHFFFAOYSA-N 0.000 description 1
- WBTYBAGIHOISOQ-UHFFFAOYSA-N pent-4-en-1-yl 2-[(2-furylmethyl)(imidazol-1-ylcarbonyl)amino]butanoate Chemical compound C1=CN=CN1C(=O)N(C(CC)C(=O)OCCCC=C)CC1=CC=CO1 WBTYBAGIHOISOQ-UHFFFAOYSA-N 0.000 description 1
- WUHLVXDDBHWHLQ-UHFFFAOYSA-N pentazole Chemical class N=1N=NNN=1 WUHLVXDDBHWHLQ-UHFFFAOYSA-N 0.000 description 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- YEBIHIICWDDQOL-YBHNRIQQSA-N polyoxin Polymers O[C@@H]1[C@H](O)[C@@H](C(C=O)N)O[C@H]1N1C(=O)NC(=O)C(C(O)=O)=C1 YEBIHIICWDDQOL-YBHNRIQQSA-N 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000001965 potato dextrose agar Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- WHHIPMZEDGBUCC-UHFFFAOYSA-N probenazole Chemical compound C1=CC=C2C(OCC=C)=NS(=O)(=O)C2=C1 WHHIPMZEDGBUCC-UHFFFAOYSA-N 0.000 description 1
- TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical class CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 1
- KKMLIVYBGSAJPM-UHFFFAOYSA-L propineb Chemical compound [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- YRRBXJLFCBCKNW-UHFFFAOYSA-N prothiocarb Chemical compound CCSC(=O)NCCCN(C)C YRRBXJLFCBCKNW-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 description 1
- XRJLAOUDSILTFT-UHFFFAOYSA-N pyroquilon Chemical compound O=C1CCC2=CC=CC3=C2N1CC3 XRJLAOUDSILTFT-UHFFFAOYSA-N 0.000 description 1
- 229960002132 pyrrolnitrin Drugs 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- WXXVQWSDMOAHHV-UHFFFAOYSA-N quinoline-7-carboxylic acid Chemical compound C1=CC=NC2=CC(C(=O)O)=CC=C21 WXXVQWSDMOAHHV-UHFFFAOYSA-N 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- HCJLVWUMMKIQIM-UHFFFAOYSA-M sodium;2,3,4,5,6-pentachlorophenolate Chemical compound [Na+].[O-]C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl HCJLVWUMMKIQIM-UHFFFAOYSA-M 0.000 description 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 235000020354 squash Nutrition 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- ROZUQUDEWZIBHV-UHFFFAOYSA-N tecloftalam Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(=O)NC1=CC=CC(Cl)=C1Cl ROZUQUDEWZIBHV-UHFFFAOYSA-N 0.000 description 1
- XQTLDIFVVHJORV-UHFFFAOYSA-N tecnazene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl XQTLDIFVVHJORV-UHFFFAOYSA-N 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical group COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01C—PLANTING; SOWING; FERTILISING
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Abstract
本发明提供了手性杀真菌剂以及含有手性杀真菌剂的组合物。还提供了本发明组合物用于抑制真菌包括植物病原真菌生长的使用方法。使用单一异构体处理特定的植物种类和杀特定真菌可使之选择性地抑制真菌生长并减少杀真菌剂的植物药害。
Description
发明技术领域
本发明涉及手性杀真菌组合物，以及使用手性杀真菌组合物抑制并治疗植物的，包括植物种子以及植物产品和作物上的真菌病害的使用方法。
发明背景
杀真菌剂具有保护所需植物免受真菌病害的重要商业价值。然而，杀真菌剂对已施用药剂的植物以及有益生物具有毒性。因此，理想的是使杀真菌剂的杀菌效果达到最大同时使之对植物的有害作用降至最低。
不同化学结构，作用机理，和优选施用方式的各种化合物都可应用作为杀真菌剂。用作杀真菌剂的典型化合物包括氯苯及其相关化合物，醌类，二羧酰亚胺，以及系统杀真菌剂包括磺酰胺类，苯并咪唑类，托布津类系统的杀菌剂，氨基嘧啶类，哌嗪类，吡啶类，咪唑类和三唑类。这些和其它杀真菌化合物公开于R.J.Cremlyn，农药(Agrochemicals)，157-216页，John Wiley & Sons，New York，NY(1991)。
杀真菌剂1-[2-(2，4-二氯苯基)-2-(丙烯氧基)乙基]-1H-咪唑，称为烯菌灵，属于咪唑类杀真菌剂。例如用于控制黄瓜、葫芦科蔬菜和观赏植物上的白粉菌，以及种薯上的镰刀菌属真菌。还用于拌种控制禾谷类病害如镰刀菌和长蠕孢属真菌引起的病害。烯菌灵还可作用于储藏病害，例如柑橘类水果，仁果类水果，香蕉和种薯上的青霉属、盘圆孢属、拟茎点霉属和茎点霉属真菌引起的病害。而且，烯菌灵对抗苯并咪唑类的植物病原真菌菌株具有杀菌活性(农药手册(The PesticideManual)，Datix International Ltd.，Bungay，Suffolk，The Bath Press，Bath，1995)。
目前使用的烯菌灵是其外消旋形式，以及至今没有使用烯菌灵单一对映异构体作为杀真菌剂的报道也没有这方面应用的建议。而且仍然需要更高效的杀真菌剂并且同时改进杀真菌毒性和植物毒性之间的平衡。另外还需要降低与应用杀真菌剂相关的费用。本发明的目的包括上述这些目的，以及其它重要目的。
发明概述
本发明的一个实施方案提供了抑制植物上的真菌生长的方法包括将杀真菌有效量的1-[2-(2，4-二氯苯基)-2-(丙烯氧基)乙基]-1H-咪唑的(S)-对映异构体，其中基本上不含(R)-对映异构体，施用至植物生长的环境中。
在本发明的另一个实施方案中杀真菌组合物包括基本上不含(R)-对映异构体的1-[2-(2，4-二氯苯基)-2-(丙烯氧基)乙基]-1H-咪唑的(S)-对映异构体和农业上可接受的载体。
在特定的优选实施方案中，以杀真菌组合物中活性成分总重量计，杀真菌组合物中(S)对映异构体的量至少约占1-[2-(2，4-二氯苯基)-2-(丙烯氧基)乙基]-1H-咪唑的90重量％。
本发明提供了防治和/或抑制与植物有关的真菌生长的有效方法。此处使用的“与...有关”的真菌包括植物或植物体内、植物种子、作物或植物产品上的真菌。影响植物生长、发育或繁殖的那些真菌也包括在内。本发明还提供了新的和有效的用于预防和控制植物、种子、农产品等的真菌病害的杀真菌组合物。下面将对本发明的这些以及其它方面进行更详细的描述。
本发明的目的在于手性杀真菌组合物，以及手性杀真菌组合物用于预防和治疗植物(包括植物种子和植物产品和作物)的真菌病害的使用方法。在一些优选实施方案中，手性杀真菌组合物包括1-[2-(2，4-二氯苯基)-2-(丙烯氧基)乙基]-1H-咪唑，以及换言之也称为烯菌灵。
优选实施方案详述
根据本发明，提供了结构式(I)的手性杀真菌化合物：
其中：R1，R2和R3各自独立地代表H，F，Cl，Br，I，OH，SH，NH2，或NO2；
R4是C1-C6烷基，C1-C6链烯基，C1-C6炔基，或烯丙基及其农业上可接受的盐，其中富含有(S)-对映异构体并优选基本上不含(R)-对映异构体。
本发明还提供了组合物其中以组合物中活性成分总重量计，含有至少约70％重量(这种情况下也可用摩尔百分数表示)的(S)-对映异构体。本发明组合物中优选含有至少约80％重量的(S)-对映异构体。更优选含有至少约85％重量的(S)-对映异构体。还更优选本发明组合物中含有至少约90％，甚至更优选至少约95％，以及仍然更优选至少约99％的(S)-对映异构体。此处使用的“活性成分”是指杀真菌活性化合物以及还可以包括本领域已知的一种或多种其它杀真菌的化合物或其它活性化合物。优选R1，R2和R3中至少一个是卤素，优选Cl。另外优选苯基部分是2，4-二氯苯基。R4优选烯丙基。在本发明的较优选实施方案中，化合物是(S)-1-[2-(2，4-二氯苯基)-2-(丙烯氧基)乙基]-1H-咪唑，也称作(S)-烯菌灵。
烯菌灵的(R)-和(S)-对映异构体是通过立体有择合成方法分别由(R)-2-氯-1-(2′，4′-二氯苯基)-1-乙醇和(S)-2-氯-1-(2′，4′-二氯苯基)-1-乙醇合成。这些化合物的对映异构体的纯度是通过手性衍生作用和卤代醇中间体的气相色谱(GC)分析确定的。Mosher酰氯(α-甲氧基-α-三氟甲基苯乙酰氯)是公知的手性衍生试剂。这种试剂已成功地应用于大量醇和胺的衍生和手性分析。当使用酰氯进行衍生时可获得两种对映异构体形式并不需要任何其它试剂。即使在恶劣的酸度、碱度和温度条件下，Mosher酰氯对外消旋化也具有显著的稳定性。使用Mosher酰氯进行手性分析的另一优点是它们固有的挥发性，使得可通过气相色谱法分析更小分子量的衍生物。已将Mosher酰氯作为衍生剂用在二异松蒎基氯硼烷(DIPCl)对2，2′，4′-三氯乙酰苯的还原产物进行手性分析。Brown等，有机化学学报(J.Org.Chem.)，1988，53，2916。衍生作用后，在Supelcowax玻璃毛细管气相色谱(GC)柱上分析非对映的Mosher酯以直接确定对映异构体过剩量。
本发明还提供了抑制植物上或植物体内的一种或多种真菌的方法。这种方法包括将杀真菌有效量的本发明组合物施用至植物的生长环境中。此处使用的对真菌生长的“抑制”定义为包括预防真菌生长、阻止生长、减缓生长和/或杀灭一种或多种真菌。因此，本发明杀真菌方法包括预防、保护、防病、系统的和根除处理。此处使用的术语“植物”包括种子、幼苗、灌木和树木。该术语还包括已经收获的水果和蔬菜，即摘后的水果，谷物和蔬菜。
本发明组合物用于抑制真菌，包括植物病原真菌生长。令人惊奇地且没有料想到地发现使用目的化合物的(S)-对映异构体获得增加的抗真菌生长作用，在某些情况下比预期高两倍，这种情况只有在用同样数量的较高活性的异构体替代较低活性的异构体时产生。例如，在葡萄糖琼脂板上测定对构巢曲霉的杀菌活性时，使用0.5微克(μg)的单一的(S)-对映异构体在与使用5μg的(R)-对映异构体时观察到的抑菌圈相等的直径圈中可以抑制真菌生长。因此，需要十倍数量的(R)-对映异构体才能获得同样程度的(S)-对映异构体抑制构巢曲霉生长的效果。
作为上述化合物抗植物病原真菌活性的实例，烯菌灵的(S)-对映异构体当使用量为38.4ppm时对白粉菌(Erysiphe graminis)的杀菌率为86.6％，类似(R)-对映异构体在使用量为58ppm时的杀菌率仅为23.3％。在使用量为76.8ppm时，(S)-对映异构体对白粉菌的杀菌率为99.3％，然而需要使用131.2ppm的外消旋物才能获得99.6％的杀菌率。
目前还没有使用烯菌灵单一对映异构体抗植物病原真菌的报道。另外也没有引起并且意识到使用单一对映异构体的技术必要性。而且，人们不会想到根据目前使用的烯菌灵，减少或完全去除外消旋物中的(R)-对映异构体部分可以解决下述问题，即提供最高活性的杀菌剂同时减少与使用没有杀菌效果或勉强有些效果的化合物相关的不必要的费用。到目前为止还没有烯菌灵的(S)-对映异构体或富含(S)-对映异构体的外消旋物商业应用的报道。
因此本发明提供了新的控制真菌的方法，包括将杀真菌有效量的结构式(I)化合物或含有该化合物的组合物施用至植物，植物的种子，植物或种子的周围环境，或已收获的水果或谷物或蔬菜。本发明化合物可直接应用于农业目的，但更合适的是使用载体或稀释剂制成组合物。因此本发明提供了杀真菌组合物包括结构式(I)化合物和可接受的载体或稀释剂。本发明某些实施方案中，上述组合物包括固体和液体制剂，其中包括0.0001％至20％重量的结构式(I)化合物。更优选该组合物包括0.001％至2.0％的结构式(I)化合物。还进一步优选本发明组合物包括0.001％至2.0％，更优选0.005％至2.0％的结构式(I)化合物。
本发明组合物可通过许多方式施用，包括本领域技术人员公知的那些方式。例如，可将组合物制剂或未制剂化的组合物直接施用至植物叶面，种子，植物正在生长或将要种植的介质中，或已采收的水果或蔬菜上。该组合物可通过喷雾，喷粉，或以乳油或糊剂施用，或通过蒸气熏蒸或以颗粒剂包括缓释颗粒剂方式施用。可将组合物施用至植物的任何部分，包括叶片，茎，枝条或根，或根周围的土壤中。另一方面，可将组合物施用至播种前的种子，或土壤，稻田水，或水培系统中。也可将组合物注射到植物中或使用电动喷雾技术或其它低容量方法喷雾蔬菜，或通过地面或空中灌溉系统施用。
当植物叶面施用时，本发明化合物可在每公顷中施用，例如约1.0g至约5kg，优选约10g至约1kg，更优选约20g至约0.4kg活性成分。
当用于拌种时，本发明化合物可在每公斤种子中施用，例如约0.0001g至约10g，优选0.005g至8g，更优选约0.005g至约4g活性成分(即结构式(I)化合物)。
用于抗植物病原真菌时，本发明组合物使用可喷粉的粉剂或颗粒剂形式，其中包括活性成分和固体稀释剂或载体，例如填料如高岭土、膨润土、硅藻土、白云石、碳酸钙、滑石、镁氧粉、漂白土、石膏、硅藻土和陶土。上述颗粒可预先制成适于土壤应用的颗粒剂而并不需要进一步处理。例如可通过将活性成分混入填料块中或使用活性成分预处理的填料块而制成颗粒剂。用于拌种的组合物可包括试剂，例如矿物油以增进组合物与种子的粘着性。另一方面，可使用有机溶剂，例如N-甲基吡咯烷酮、丙二醇或N，N-二甲基甲酰胺将活性成分制成拌种剂。本发明组合物可使用水分散性粉剂或水分散性颗粒剂形式并可包括湿润或分散剂以有利于其在液体中分散。上述粉剂或颗粒剂还可包括本领域技术人员公知的填料和悬浮剂。
本发明组合物可制成可溶性粉剂或颗粒剂，或极性溶剂溶液。可溶性粉剂是将活性成分与水溶性盐如碳酸氢钠、碳酸钠、硫酸镁或多糖混合，并加入湿润剂或分散剂以增进水分散性和/或溶解性而制成。然后将混合物研磨成细粉。类似地也可将组合物造粒制成水溶性颗粒剂。可将活性成分溶解在极性溶剂如酮、醇和乙二醇醚中制备溶液制剂。上述溶液可任选含有一种或多种表面活性剂以增进在含水介质中的溶解或悬浮并防止在喷雾罐中产生结晶。
通过将所有活性成分溶解在任选含有湿润剂或乳化剂的有机溶剂中，然后把混合物加入水中来制备可乳化的浓缩物或乳剂，其中任选含有湿润剂或乳化剂。适合的有机溶剂包括芳烃溶剂如烷基苯和烷基萘，酮如环己酮和甲基环己酮，氯化烃如氯苯和三氯乙烷，以及醇如苄醇、糠醇、丁醇和乙二醇醚。
不溶或难溶固体的浓缩水悬浮剂可通过球磨或粉磨将其与分散剂研磨制备，并含有悬浮剂以减少固体沉降。通过喷雾施用的组合物可采用气雾剂形式，其中借助推进剂的压力将制剂装入容器中。作为推进剂，氟三氯甲烷或二氯二氟甲烷是适合的。
如需要，本发明组合物可使用烟剂，通过将干燥的活性成分与烟火混合物混合制成适于在封闭空间内产生含化合物的烟雾组合物。还有另一种选择是，可以将本发明化合物制成微胶囊化制剂，或制成可生物降解的聚合物形式的制剂，由此活性物质可缓慢、控制释放。
通过加入适合的添加剂，例如增进吸收、展布、粘着力和已处理表面的耐雨水性的添加剂，可以使不同组合物更好地适应各种施用方式。本领域已知的适合的添加剂包括可增进各种制剂生物活性的添加剂。这些添加剂包括表面活性剂，可增进经制剂处理表面的湿润性能和固着性，以及活性物质的吸收和流动性。其它适合的添加剂包括油基喷雾添加剂，例如某些矿物油和天然植物油，例如豆油和菜籽油。上述以及其它添加剂可与其它助剂混合使用。
本发明化合物可与肥料，例如含氮、钾或磷肥料混合使用。例如含一种或多种肥料的组合物可以是颗粒剂形式，并且这种颗粒剂可适当含有至多约25％重量的活性成分。
本领域技术人员可以理解水分散性粉剂，浓缩乳剂和浓缩悬浮剂可含有一种或多种表面活性剂，它们的功能是作为湿润剂、分散剂、乳化剂、和/或悬浮剂。这些表面活性剂可以是阳离子、阴离子或非离子表面活性剂。适合的阳离子表面活性剂包括季铵盐化合物，例如十六烷基三甲基溴化铵。适合的阴离子表面活性剂包括皂类，脂族硫酸单酯盐，例如月桂基硫酸钠，以及磺化芳烃化合物盐，例如十二烷基苯磺酸钠、木素磺酸、丁基萘磺酸的钠、钙或铵盐，或二异丙基-和三异丙基萘磺酸钠的混合物。适合的非离子表面活性剂包括环氧乙烷与脂族醇如十八烷或十六烷醇，或与烷基酚如辛基-或壬基酚和辛基甲酚的缩合产物。其它适合的非离子表面活性剂包括由长链脂肪酸衍生的偏酯，以及己糖醇酐、烷基葡萄糖苷、多糖、和卵磷脂，以及上述偏酯与环氧乙烷缩合产物。适合的悬浮剂包括亲水的胶体如聚乙烯吡咯烷酮和羧甲基纤维素钠，以及膨胀粘土如膨润土和硅镁土。
使用含水分散液或乳剂形式的组合物通常以含高比例活性成分的浓缩液形式供应，浓缩液在使用前用水稀释。这些浓缩液应优选可耐长期储藏，以及储藏后可用水稀释形成可在足够长的时间内保持均匀的含水制剂从而使之可用常规喷雾装置施用。通常浓缩液可含有至多95％，适合的1％-85％，例如1％-25％或25％-60％重量的活性成分。稀释形成含水制剂后，根据使用目的不同这些制剂可含有各种剂量的活性成分，可以施用含0.0001％-20％，例如0.001％-2％重量活性成分的含水制剂。
含结构式(I)化合物的本发明组合物可与土壤、泥煤或其它根部介质混合用以保护植物免受种传、土传或叶部真菌病害的侵染。
本发明组合物可含有其它生物活性化合物。可与本发明化合物混合使用的适合的生物活性化合物包括那些类似的或互补杀真菌活性化合物或植物生长调节物质、除草剂或杀虫剂。当组合物中含有其它杀真菌化合物时，组合物将具有更广谱的活性或比单一的结构式(I)化合物更高的(固有)杀菌活性。某些情况下，一种或多种其它杀菌剂对结构式(I)化合物具有增效杀菌活性。可用于本发明组合物中的其它杀真菌化合物包括(R，S)-1-氨基丙基膦酸；(R，S)-4-(4-氯苯基)-2-苯基-2-(1，2，4-三唑-1-基甲基)丁腈；(Z)-N-丁-2-烯氧基甲基-2-氯-2′，6′-二乙基乙酰苯胺；1-(2-氰-2-甲氧基亚氨乙酰基)-3-乙基脲；4-(2，2-二氟-1，3-苯并二氧戊环-4-基)吡咯-3-腈；4-溴-2-氰基-N，N-二甲基-6-三氟甲基苯并咪唑-1-氨磺酰；5-乙基-5，8-二氢-8-氧代(1，3)-二氧戊环-(4，5-g)喹啉-7-羧酸；α-[N-(3-氯-2，6-二甲苯基)-2-甲氧基乙酰氨基]-γ-丁内酯；N-(2-甲氧基-5-吡啶)-环丙烷甲酰胺；棉铃威；aldimorph氨丙膦酸；敌菌灵；氧环唑；醚菌酯；苯霜灵；苯菌灵；联苯三唑醇；乐杀螨；联苯三唑醇；灭瘟素；糠菌唑；乙嘧酚磺酸酯，丁烯草胺，丁硫啶，敌菌丹，克菌丹，多菌灵，多菌灵盐酸盐，萎锈灵，灭螨猛，氯代苄噻酮(chlorbenzthiazone)，地茂散，百菌清，乙菌利(chlorozolinate)，clozylacon，含铜化合物如王铜，羟基喹啉铜，硫酸铜，树脂酸铜，以及波尔多液；放线菌酮；霜脲氰；环丙唑醇；酯菌胺；咪菌威；二-2-吡啶基二硫化物1，1′-二氧化物；抑菌灵；二氯萘醌；苄氯三唑醇；哒菌清；氯硝胺；二癸基二甲基氯化铵；乙霉威；恶醚唑；O，O-二-异丙基-5-苄基硫代磷酸酯；dimefluazole；dimetconazole烯酰吗啉；甲菌定；烯唑醇；敌螨普；吡菌硫；灭菌磷；二噻农；吗菌灵；多果定；多果定；克瘟散；氧唑菌；乙环唑；乙菌定；促长啉；(Z)-N-苄基-N-([甲基(甲基-硫代亚乙基氨基-氧代羰基)氨基]硫代)-β-丙氨酸乙酯；氯唑灵；地可松；菌拿灵；异嘧菌醇；腈苯唑；呋菌胺；拌种咯；苯锈啶；丁苯吗啉；薯瘟锡；毒菌锡；福美铁；嘧菌腙；氟啶胺；氟恶菌；氟酰亚胺；喹唑菌酮；氟硅唑；氟酰胺；粉唑醇；灭菌丹；麦穗宁；呋氨丙灵；呋醚唑；双胍辛醋酸盐；己唑醇；土菌消；土菌消；腈嘧菌酯；酰胺唑；环戊唑醇；异稻瘟净；异丙定；异丙烯基丁基氨基甲酸盐；富士一号；春雷霉素；代森锰锌；代森锰；嘧菌胺；丙氧灭绣胺；甲霜灵；环戊唑菌；甲呋菌胺；代森联；代森联；噻菌胺；腈菌唑；甲胂铁铵；福美镍；异丙消；氟苯嘧啶醇；甲呋酰胺；有机汞化合物；恶霜灵；喹菌酮；氧化萎锈灵；稻瘟酯；戊菌唑；戊菌隆；叶枯净；藻菌磷(乙磷铝)；磷酸；四氯苯酞；多氧霉素；二硫代森联；噻菌灵；丙氯灵；杀菌利；百维灵；百维灵单盐酸盐；丙环唑；甲基代森锌；丙酸；胺丙威；比锈灵；定菌磷；啶斑肟；二甲嘧菌胺；咯喹酮；氯吡呋醚；硝吡咯菌素；季铵化合物；唑喹菌酮；灭螨猛；五氯硝基苯；吡咪唑菌(rabenazole)；五氯酚钠；链霉素；硫；叉氨苯酰胺；戊唑醇；叶枯酞；四氯硝基苯；氟醚唑；涕必灵；噻菌腈；溴氟唑；2-(氰硫基甲硫基)苯并噻唑；甲基托布津；福美双；timibenconazole；甲基立枯磷；对甲抑菌灵；1，1′-亚氨基二(八亚甲基)双胍三乙酸盐；三唑酮；唑菌醇；叶锈特；唑菌嗪；三环唑；十三吗啉；嗪氨灵；氟菌唑；戊叉唑菌；井冈霉素；威百亩；烯菌酮；氟苄酰胺；代森锌；和福美锌。
以下实施例仅用于解释本发明，无论如何并不应理解为本发明范围的限制。这些实施例及其类似实施例，使本领域技术人员更清楚地理解本发明内容和随后的权利要求书。
实施例
实施例1外消旋烯菌灵的合成
2-溴-2′，4′-二氯乙酰苯：将25g(0.1322mol)的2′，4′-二氯乙酰苯放入装有磁力搅棒、回流冷凝器和滴液漏斗的三口圆底烧瓶中。加入无水醚(30ml)和AlCl3(0.20g)。将瓶口塞好并在冰浴中冷却至0℃。逐滴(速率约为0.5ml/min)加入Br2(21.13g，0.1322mol)。加入Br2的操作完成后，减压条件下除去HBr和溶剂。通过在橙色油状产物上吹送氮气流除去残留的HBr。将获得的油状产物放于高真空中直至冒泡全部停止。获得的产物是粘稠的橙色的油，冰箱储藏时固化。产率：35.72g(100％)；TLC：95％正己烷/5％丙酮，Rf＝0.35。
2-(1H-咪唑)-2′，4′-二氯乙酰苯：将2-溴-2′，4′-二氯乙酰苯(35.72g；0.1322mol)溶解在250ml的无水醚中。将上述溶液过滤至1升圆底烧瓶中以去除溴化反应中残留的不溶的铝盐。加入咪唑(17.70g，0.26mol)，并在室温下搅拌溶液4小时。搅拌4小时后，在圆底烧瓶底部形成不溶的橙色油。加入乙醇(85ml)，并将溶液搅拌过夜。过滤溶液去除粉红色的固体副产物，用少量醚洗副产物并干燥(5.50g)。合并的洗液和滤液用400ml的10％NaOH处理。分离各相并用150ml醚萃取水相。合并有机相。将合并的醚层在冷藏箱中冷却过夜，将过滤获得的固体用无水醚洗并干燥。产率：13.50g(40％)；m.p.61-64℃。1-(2′，4′-二氯苯基)-2-(1H-咪唑)-1-乙醇：
(a)将2-(1H-咪唑)-2′，4′-二氯乙酰苯(8g，31.36mmol)和甲醇(100ml)放入装有磁力搅拌棒的250ml圆底烧瓶中。加入NaBH4(1.20g，31.72mmol)，在室温下将溶液搅拌45分钟。再加入0.30g NaBH4并再将溶液搅拌3小时。将获得的溶液在醚和水(300ml，1∶1)之间分配，分离醚层并将其放于冷藏箱过夜。通过过滤获得相应的晶体，并用无水醚洗。然后将产物在减压条件下干燥，获得白色固体。产率：7g(87％)；m.p.129-132℃。
(b)1-(2′，4′-二氯苯基)-2-(1H-咪唑)-1-乙醇的另一种制备方法如下。将由硼氢化钠还原2，2′，4′-三氯乙酰苯(购自Aldrich Chemical)制备的4g(17.74mmol)的(±)-2-氯-(2′，4′-二氯苯基)-1-乙醇，和5.00g(73.44mmol)的咪唑溶解在含有15ml的干燥2-丁酮的100ml的装有磁力搅棒和回流冷凝器的圆底烧瓶中。加入4g K2CO3和催化量的NaI并将溶液在氮气中回流36小时。在室温下冷却后，将反应混合物过滤。向滤液中加入醚并将所得溶液用50ml水洗而分层。每次用50ml醚萃取水层3次。将醚萃取物与先前的有机相合并，然后用无水MgSO4充分干燥。过滤去除MgSO4后，将滤液浓缩获得黄色油状物。粗产物经色谱法(CH2Cl2∶CH3OH/95∶5)获得3.59g纯化的淡黄色结晶(78.7％产率)。1-(β-烯丙氧基-β-2′，4′-二氯苯基乙基)咪唑(烯菌灵)：
(a)将1-(2′4′-二氯苯基)-2-(1H-咪唑)-1-乙醇(5g，19.45mmol)溶解在含有83ml无水THF的装有磁力搅棒并封有橡胶隔片的250ml圆底烧瓶中。向烧瓶中吹送氮气，加入NaH(0.52g，21.67mmol)。立即用橡胶隔片塞好烧瓶。将与出口管相连的针经隔片引入烧瓶，以排出氢气。约30分钟后，当氢气的排放减弱时，通过注射器向正在搅拌的溶液中缓慢加入2.10ml(2.94g，24.3mmol)烯丙基溴。将溶液在室温下搅拌过夜，然后倒入100ml水中并用醚萃取。再用100ml水洗橙色醚层并分液。用无水MgSO4干燥醚层，过滤，蒸发获得粘稠金黄色的油状物烯菌灵自由碱。产率：5g(87％)；TLC：丙酮，Rf＝0.50。
(b)(±)-1-(β-烯丙氧基-β-(2′，4′-二氯苯基乙基))咪唑的另一种制备方法如下。将0.17g(0.66mmol)的(±)-α-(2′4′-二氯苯基)-1H-咪唑-1-乙醇溶解在含7ml干燥的二噁烷的25ml圆底烧瓶中。在氮气氛下边搅拌边向溶液中加入氢化钠(0.1g；4.2mmol)和0.1gNaCl。将混合物加热至35℃并加入0.5ml烯丙基氯。再过5分钟后，将混合物加热至50℃并再加入0.5ml烯丙基氯。通过TLC监控反应过程，当反应完成后，将混合物冷却，然后用水猝灭反应。将全部内容物用100ml醚萃取3次，合并的醚萃取液用饱和的NaHCO3溶液洗，并用无水MgSO4干燥有机层。去除干燥剂后，浓缩滤液，获得黄色油状粗产物。用色谱法纯化(CH2Cl2∶CH3OH/95∶5)后获得淡褐色粘稠的油状物并随后固化的(±)烯菌灵(0.159g)；产率：81％。
实施例2(R)-(-)-烯菌灵的合成
(R)-2-氯-(2′，4′-二氯苯基)-1-乙醇：在氮气下，-25℃(干冰，CCl4)下向含16g(49.90mmol)(-)-DIP-Cl的30ml无水THF溶液中加入10g(44.74mmol)2，2′，4′-三氯乙酰苯。将瓶口塞好并在-25℃下搅拌约7小时，然后室温过夜。在真空下去除THF，并在高真空室温过夜条件下去除(+)-α-蒎烯。将所得的粘稠的无色油溶解在200ml无水醚中，并冷却至0℃。向滤液中加入二乙醇胺(10.50g，0.10mol)，并在室温下继续搅拌3小时。过滤转移获得的白色固体并用无水醚洗。将无色溶液蒸发至干燥产生粘稠的无色油。将上述油用硅胶闪色谱法分析，首先用己烷去除(+)-α-蒎烯。用93％己烷/7％丙酮从柱上洗脱产物获得11.30g白色固体。该固体在0℃由己烷中结晶。产率：5.75g(57％)；TLC：95％己烷/5％丙酮，Rf＝0.10。
(R)-2-碘-(2′，4′-二氯苯基)-1-乙醇：将(R)-2-氯-(2′，4′-二氯苯基)-1-乙醇(1.95g，8.65mmol)溶解在60ml无水丙酮(4A分子筛)中。然后向溶液中加入NaI(7g，46.70mmol)并将溶液在氮气下回流3小时。冷却至室温时，将溶液倒入160ml己烷/乙酸乙酯(3∶1)中，并过滤去除过量的已沉淀的NaI。真空蒸发滤液至干燥，用醚处理并由固体NaI中倾析剩余物。当去除醚后，获得白色固体产物。产率：2.40g(88％)。(R)-α-(2′，4′-二氯苯基)-1H-咪唑-1-乙醇：
(a)将2.40g(7.57mmol)(R)-2-碘-(2′，4′-二氯苯基)-1-乙醇用约6ml三乙胺和咪唑(2.50g，36.7mmol)处理。将溶液在氮气下加热，并且氮气流流速足够快以使三乙胺由反应混合物中蒸发。当几乎所有三乙胺蒸发后，将反应混合物在95-100℃加热约6小时。冷却后，将黄色粘稠剩余物在水和醚中分配。由水层分离出醚层并用水洗醚层。然后将醚层蒸发至干燥，将所得剩余物放在高真空下以去除残留的挥发性物质。获得高粘性的黄色油状产物。产率：1.61g(83％)；[α]D 23＝-67.7。(c＝16.1，MeOH)。
(b)(R)-对映异构体也可使用实施例1制备类似物质的外消旋形式所述的类似方法(b)由(R)-2-氯-(2′，4′-二氯苯基)-1-乙醇制备。(R)-(-)-1-(β-烯丙氧基-β-2′，4′-二氯苯基乙基)咪唑：
(a)将2.05g(7.97mmol)的(R)-α-(2′，4′-二氯苯基)-1H-咪唑-1-乙醇溶解在含有40ml无水THF的装有磁力搅棒并封有橡胶隔片的250ml圆底烧瓶中。将溶液用氮气吹洗，并向搅拌着的溶液中加入0.21g(8.75mmol)的NaH。30分钟后，室温氮气下向正在搅拌的溶液中加入1.10g(9.09mmol)烯丙基溴。将塞好瓶口并在室温下搅拌24小时。然后，加入120ml水，并用醚萃取溶液。用饱和盐水洗醚层，用无水MgSO4干燥醚层，过滤，蒸发获得1.96g粘稠的金黄色油状的粗(R)-(-)-烯菌灵(粗产物产率：83％)。将上述油溶解在约30ml醚中，向正在搅拌的溶液中加入含0.65g(6.63mmol)H2SO4的5ml水溶液。真空下去除溶剂获得2.61g高粘度，红色油状物。硫酸盐经过硅胶色谱纯化，首先用丙酮洗脱，然后用丙酮/甲醇(2∶1)洗脱，获得1.90g盐。[α]D 23＝-56.6°(c＝7.6，MeOH)。将盐转化为它的游离碱形式，并用硅胶色谱纯化，获得0.95g(R)-(-)-烯菌灵。[α]D 23＝-77.9°(c＝9.5，MeOH)。
(b)(R)-(-)-对映异构体也可与实施例1制备外消旋物所述方法(b)的类似方式由(R)-α-(2′，4′-二氯苯基)-1H-咪唑-1-乙醇制备获得。
实施例3(S)-(+)-烯菌灵的合成
(S)-2-氯-(2′，4′-二氯苯基)-1-乙醇：在氮气下，-25℃(干冰，CCl4)下向含16g(49.90mmol)(+)-DIP-Cl的30ml无水THF溶液中分批加入10g(44.74mmol)2，2′，4′-三氯乙酰苯。将塞好瓶口并在-25℃下搅拌约7小时，然后保持在室温氮气下2天。加入100ml 10％HCl，用醚萃取溶液。用100ml水洗醚层，然后真空浓缩。将所得无色油放在高度真空下7小时，边搅拌边去除(-)-α-蒎烯。将油溶解在250ml醚中，并冷却至0℃。向溶液中加入二乙醇胺(10.50g，0.10mol)，并在0℃下继续搅拌10分钟。移去冰浴并将溶液在室温下搅拌2.5小时。过滤溶液，用醚洗固体。当除去醚后，获得15.50g稍微粘稠的黄色油状物。将上述油用硅胶色谱纯化，首先用己烷洗脱去除α-蒎烯，然后用己烷/丙酮(93％/7％)洗脱出白色固体产物醇。该固体在0℃在己烷中结晶，获得纯化的针状的白色结晶状固体的卤代醇。产率：4.80g(43％)。
(S)-2-碘-(2′，4′-二氯苯基)-1-乙醇：将(S)-2-氯-(2′，4′-二氯苯基)-1-乙醇(4g，17.74mmol)溶解在100ml无水丙酮(4A分子筛)中。用氮气吹洗溶液，然后向溶液中加入NaI(12.75g，85.10mmol)并将溶液在氮气下回流3.5小时。冷却至室温时，将溶液边搅拌边倒入约320ml己烷/乙酸乙酯(3∶1)中。然后将溶液过滤去除过量的已沉淀的NaI。真空蒸发滤液至干燥获得黄色油状物。倾析出油状物，用醚处理剩余物，并由固体NaI中倾析醚冲洗液。合并醚溶液并蒸发至干燥。去除醚后，获得黄色结晶状固体产物。产率：4.70g(84％)。(S)-α-(2′，4′-二氯苯基)-1H-咪唑-1-乙醇：
(a)将4.70g(14.83mmol)(S)-2-碘-(2′，4′-二氯苯基)-1-乙醇和5g(73.44mmol)咪唑加入11ml三乙胺中。将溶液在氮气下回流，并且氮气流流速足够快以使三乙胺由反应混合物中蒸发。当几乎所有三乙胺蒸发后，将反应混合物在95-100℃氮气下加热约8小时。冷却后的溶液在水和醚中分配，并去除水层。用水洗醚层并分液。然后将醚层蒸发至干燥，将所得剩余物溶解在40ml甲醇中。真空下去除甲醇，获得高粘性的淡黄色油状产物。产率：3.50g(92％)；[α]D 23＝+68.6°(c＝14，MeOH)。
(b)(S)-对映异构体也可使用实施例1制备外消旋物所述的(b)的类似方法由(S)-α-氯-(2′，4′-二氯苯基)-1-乙醇制备。(S)-(+)-1-(β-烯丙氧基-β-2′，4′-二氯苯基乙基)咪唑：
(a)将2.93g(11.40mmol)的(S)-α-(2′4′-二氯苯基)-1H-咪唑-1-乙醇溶解在含有50ml无水THF的装有磁力搅棒并封有橡胶隔片的250ml圆底烧瓶中。将溶液用氮气吹洗，并在氮气下向搅拌着的溶液中加入0.30g(12.50mmol)的NaH。30分钟后，室温氮气下向正在搅拌的溶液中加入1ml(15.56mmol)烯丙基溴。塞好瓶口并在室温下搅拌24小时。然后，加入约120ml水，并用醚萃取溶液。用饱和盐水洗醚层，用无水MgSO4干燥醚层，过滤，蒸发获得2.55g粘稠的金黄色油状的粗(S)-(+)-烯菌灵(粗产物产率：75％)，[α]D 23＝+69.6°(c＝10.2，MeOH)。在上述油中加入12ml水，然后向正在搅拌的溶液中加入含0.84g(8.58mmol)H2SO4的5ml水溶液。然后高度真空下并微加热去除水。剩余物经过硅胶色谱纯化，首先用丙酮洗脱以去除少量的极性杂质，然后用丙酮/甲醇(3∶1)洗脱，获得2.30g淡黄色半固体硫酸盐。[α]D 23＝+59.8°(c＝9.2，MeOH)。将盐转化为它的游离碱形式，并用硅胶色谱纯化，获得1.37g(S)-(+)-烯菌灵。[α]D 23＝+81.0°(c＝13.7，MeOH)。
(b)(S)-(+)-对映异构体也可与实施例1制备类似的外消旋物所述方法(b)的类似方式由(S)-α-(2′，4′-二氯苯基)-1H-咪唑-1-乙醇制备获得。
实施例4烯菌灵合成过程中制备的卤代醇中间体的手性GC分析
将15mg纯卤代醇中间体样品溶解在含5滴无水吡啶的400μl无水THF的Reacti-Vial中。在上述溶液中加入20mg(R)-(-)-α-甲氧基-α-三氟甲基苯基乙酰氯，搅拌溶液。几乎立即形成大量吡啶盐酸盐沉淀。将溶液保持室温过夜。将10％NaOH(1ml)加入溶液，用醚萃取溶液。丢弃水相并用水洗有机相(醚层)。浓缩醚层，获得约30mg高粘度无色油状物。将油溶解在甲醇中，用水稀释至50ml，用于随后的GC分析。GC柱：Supelcowax10熔凝硅石毛细管柱，15m，0.53mmI.D.，1.0μM；
条件：200℃等温；产物非对映酯的保留时间：(R，R)＝16.93分钟，(S，R)＝15.42分钟。
在上述条件下注入Mosher酸空白对照(上述方法但没有卤代醇)。在色谱中没有观察到峰。发现未衍生的卤代醇的保留时间为3.66分钟。测定的卤代醇的(R)对映异构体允许误差为99.0％，以及发现(S)-对映异构体允许误差至少为99.9％，没有检测到可统计量的(R)-对映异构体。这些卤代醇的光学纯度值与文献中报道的数值一致。Brown等，有机化学学报(J.Org.Chem.)，1988，53，2916。实施例5(R)-1-[2-(2，4-二氯苯基)-2-(丙烯氧基)乙基]-1H-咪唑(烯菌灵)的效果对构巢曲霉的杀菌活性
根据标准稀释方法制备外消旋和单一对映异构体的烯菌灵丙酮溶液。每一溶液以5微升(μl)等份点在预先用构巢曲霉接种物处理的10cm马铃薯葡萄糖琼脂板的中心。在未处理板(对照)上，接种物在3天内长成菌落。引入计算杀菌剂的抑菌率，观察抑菌圈，根据使用的杀菌化合物(即外消旋物或单一对映异构体)的浓度和同一性产生不同大小的抑菌圈。结果列于表1中。
表1
| 抑菌圈直径(cm) | |||||
| 异构体 | 50μg | 5μg | 0.5μg | 0.05μg | 0.005μg |
| (R，S) | 6.0-6.5 | 3.5-4.0 | 2.0-2.5 | 0 | 0 |
| (R) | 4.0-4.5 | 2.5-3.0 | 1.0-1.5 | 0 | 0 |
| (S) | 6.0-6.5 | 4.0 | 2.5-3.0 | 0 | 0 |
根据上述的抑菌圈大小，(S)对映异构体在给定浓度下效果是同样浓度的(R)-对映异构体的10倍。
实施例61-[2-(2，4-二氯苯基)-2-(丙烯氧基)乙基]-1H-咪唑的外消旋物和单一对映异构体对小麦上的白粉菌(Erysiphe graminis)的杀菌效果
将测试化合物制成在水中含有5％丙酮和0.25％TritonX-155TM表面活性剂的混合物，浓度列于表2。用指定浓度的测试化合物喷雾小麦，使用手动喷雾器并要求叶片被全部润湿。每个浓度喷雾三株植物。将植物干燥2小时，然后用真菌无性繁殖体悬浮液喷雾植物以接种禾白粉菌(Erysiphe graminis f.sp.graminis)。将接种后的植物培育在适于真菌生长的条件下。未喷雾的、接种的植物作为对照以观察未进行防治的真菌病害发展情况。
当真菌病害产生症状时，确定处理后的植物的病害控制百分率。还确定对照植物的病害组织百分率。病害控制率采用0-100％的分级水平评价。结果表示在表2中。未处理的对照植物的病害组织约占总植物组织的90％。
还测定ED50(获得50％杀菌率所需的估算浓度)和ED90(获得90％杀菌率所需的估算浓度)，并表示在表3中。
表2
| 外消旋物和单一对映异构体对白粉菌的控制 | ||
| 化合物 | 使用浓度，ppm | 控制百分率 |
| (R)-对映异构体 | 116 | 80 |
| 58 | 23.3 | |
| 29 | 0 | |
| 14.5 | 0 | |
| 7.25 | 0 | |
| 外消旋物 | 131.2 | 99.6 |
| 65.6 | 98.6 | |
| 32.8 | 73.3 | |
| 16.4 | 60 | |
| 8.2 | 40 | |
| (S)-对映异构体 | 153.6 | 100 |
| 76.8 | 99.3 | |
| 38.4 | 86.6 | |
| 19.2 | 60 | |
| 9.6 | 26.6 | |
表3
| 单一异构体和外消旋物对植物病原菌的杀菌效果 | ||||||
| Pi | Po | Bc | Eg | Pr | ||
| (R)-异构体 | ||||||
| ED50(ppm) | 50 | 8 | 43 | 81 | 39 | |
| ED90(ppm) | 407 | 70 | 72 | 137 | 109 | |
| 外消旋物 | ||||||
| ED50(ppm) | 31 | 14 | 38 | 12 | 17 | |
| ED90(ppm) | 149 | 44 | 65 | 47 | 34 | |
| (S)-异构体 | ||||||
| ED50(ppm) | 21 | 6 | 42 | 16 | 17 | |
| ED90(ppm) | 166 | 50 | 93 | 41 | 31 | |
关键词：
Pi致病疫霉(晚疫病)； 测试植物： 番茄
Po稻梨孢(稻瘟病)； 测试植物： 水稻
Bc灰葡萄孢(灰霉病)； 测试植物： 胡椒
Eg禾白粉菌(白粉病)； 测试植物： 小麦
Pr隐匿柄锈菌(叶锈病)； 测试植物： 小麦
结果显示(S)对映异构体的效果高于外消旋物或(R)异构体。除了上述那些内容以外，本发明还有各种改进，本领域技术人员根据前述内容可以显而易见地获得。这些改进也在附带的权利要求保护范围之内。
Claims (11)
1.抑制与植物相关的真菌生长的方法，该方法包括将杀真菌有效量的1-[2-(2，4-二氯苯基)-2-(丙烯氧基)乙基]-1H-咪唑的(S)-对映异构体，其中基本上不含(R)-对映异构体，施用至植物生长环境中。
2.权利要求1的方法，其中所述真菌是曲霉属、禾白粉菌属、青霉属、盘圆孢属、拟茎点霉属、镰刀菌属或茎点霉属。
3.权利要求1的方法，其中所述植物是水果，蔬菜或观赏植物。
4.权利要求3的方法，其中所述植物是水果或蔬菜。
5.权利要求1的方法，其中所述植物是禾本科植物。
6.权利要求5的方法，其中所述禾本科植物是谷类植物。
7.权利要求1的方法，其中所述植物是种子。
8.杀真菌组合物，该组合物包括基本上不含(R)-对映异构体的1-[2-(2，4-二氯苯基)-2-(丙烯氧基)乙基]-1H-咪唑的(S)-对映异构体和农业上可接受的载体。
9.权利要求8的组合物，其中以所说的组合物中含有的1-[2-(2，4-二氯苯基)-2-(丙烯氧基)乙基]-1H-咪唑的总量计，所述(S)-对映异构体的量至少约为90％。
10-杀真菌组合物，该组合物富含1-[2-(2，4-二氯苯基)-2-(丙烯氧基)乙基]-1H-咪唑的(S)-对映异构体。
11.权利要求10的组合物，其中所述富含至少约为75摩尔百分数。
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| CN100382801C (zh) * | 2006-03-14 | 2008-04-23 | 北京大学 | α-(2,4-二氯苯基)-1H-咪唑-1-乙醇在制备治疗肝炎的药物中的用途 |
| CN104610155A (zh) * | 2015-02-06 | 2015-05-13 | 临海市利民化工有限公司 | 一种抑霉唑的制备方法 |
| CN111134127A (zh) * | 2019-12-26 | 2020-05-12 | 武汉回盛生物科技股份有限公司 | 禽舍用恩康唑喷雾剂及其制备方法 |
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| US5976159A (en) * | 1995-02-24 | 1999-11-02 | Heartport, Inc. | Surgical clips and methods for tissue approximation |
| AU6762400A (en) * | 1999-08-12 | 2001-03-13 | Cor Therapeutics, Inc. | Inhibitors of factor xa |
| US7091353B2 (en) | 2000-12-27 | 2006-08-15 | Celgene Corporation | Isoindole-imide compounds, compositions, and uses thereof |
| US20040116016A1 (en) * | 2002-12-13 | 2004-06-17 | Yadollah Delaviz | Method for the addition of anti-microbial compounds to fiberglas insulation products |
| DE602005002236T2 (de) * | 2004-02-04 | 2008-05-15 | Janssen Pharmaceutica N.V. | Synergistische antifungale ddac-zusammensetzungen |
| NZ583584A (en) * | 2005-09-29 | 2010-05-28 | Janssen Pharmaceutica Nv | Synergistic antifungal combinations of imazalil and fosetyl-Al (aluminum tris(ethyl phosphite)) |
| JP2009535377A (ja) * | 2006-05-02 | 2009-10-01 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | イマザリルを含んでなる殺生物性組み合わせ |
| CN101647441B (zh) * | 2009-07-31 | 2012-10-03 | 深圳诺普信农化股份有限公司 | 一种含嘧菌酯的杀菌组合物及其应用 |
| CN110437154A (zh) * | 2019-09-10 | 2019-11-12 | 武汉川泰科技有限公司 | 一种恩康唑原料药的制备方法 |
| CN110845416A (zh) * | 2019-11-19 | 2020-02-28 | 武汉回盛生物科技股份有限公司 | 一种α,β-二芳基取代乙醇的O-烯丙基化方法 |
| CN115028586A (zh) * | 2022-06-27 | 2022-09-09 | 池州中瑞化工有限公司 | 一种手性（s）-抑霉唑的制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100382801C (zh) * | 2006-03-14 | 2008-04-23 | 北京大学 | α-(2,4-二氯苯基)-1H-咪唑-1-乙醇在制备治疗肝炎的药物中的用途 |
| CN104610155A (zh) * | 2015-02-06 | 2015-05-13 | 临海市利民化工有限公司 | 一种抑霉唑的制备方法 |
| CN111134127A (zh) * | 2019-12-26 | 2020-05-12 | 武汉回盛生物科技股份有限公司 | 禽舍用恩康唑喷雾剂及其制备方法 |
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| MXPA01006686A (es) | 2003-07-21 |
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