CN1368965A - 异噁唑啉衍生物和含此为有效成分的除草剂 - Google Patents
异噁唑啉衍生物和含此为有效成分的除草剂 Download PDFInfo
- Publication number
- CN1368965A CN1368965A CN00811393A CN00811393A CN1368965A CN 1368965 A CN1368965 A CN 1368965A CN 00811393 A CN00811393 A CN 00811393A CN 00811393 A CN00811393 A CN 00811393A CN 1368965 A CN1368965 A CN 1368965A
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- Prior art keywords
- alkyl
- group
- halogen atom
- alkoxyl group
- substituted
- Prior art date
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- Granted
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- 150000002547 isoxazolines Chemical class 0.000 title claims abstract description 17
- 239000004009 herbicide Substances 0.000 title abstract description 3
- 239000004480 active ingredient Substances 0.000 title abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 12
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 10
- -1 aminocarboxyl Chemical group 0.000 claims description 48
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 48
- 125000003545 alkoxy group Chemical group 0.000 claims description 32
- 125000005843 halogen group Chemical group 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 125000004414 alkyl thio group Chemical group 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000003282 alkyl amino group Chemical group 0.000 claims description 9
- 239000000470 constituent Substances 0.000 claims description 9
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 8
- 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 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 4
- 150000001336 alkenes Chemical class 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 2
- 125000004691 alkyl thio carbonyl group Chemical group 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 2
- 230000002363 herbicidal effect Effects 0.000 abstract description 43
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 3
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 113
- 125000001309 chloro group Chemical group Cl* 0.000 description 87
- 238000006243 chemical reaction Methods 0.000 description 40
- 125000001246 bromo group Chemical group Br* 0.000 description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 34
- 238000002360 preparation method Methods 0.000 description 31
- 239000002904 solvent Substances 0.000 description 26
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 21
- 125000000217 alkyl group Chemical group 0.000 description 15
- 239000004563 wettable powder Substances 0.000 description 15
- 238000009472 formulation Methods 0.000 description 14
- 239000002689 soil Substances 0.000 description 14
- 241000196324 Embryophyta Species 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 238000001035 drying Methods 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 230000006837 decompression Effects 0.000 description 9
- 231100000572 poisoning Toxicity 0.000 description 9
- 230000000607 poisoning effect Effects 0.000 description 9
- 238000010992 reflux Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000009331 sowing Methods 0.000 description 8
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 7
- 239000003513 alkali Substances 0.000 description 7
- 150000003568 thioethers Chemical class 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 244000058871 Echinochloa crus-galli Species 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 150000002170 ethers Chemical class 0.000 description 6
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000004033 plastic Substances 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- 240000007594 Oryza sativa Species 0.000 description 5
- 235000007164 Oryza sativa Nutrition 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 235000009566 rice Nutrition 0.000 description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
- 241001597008 Nomeidae Species 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 4
- 150000001555 benzenes Chemical class 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 235000019241 carbon black Nutrition 0.000 description 4
- 239000006229 carbon black Substances 0.000 description 4
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 description 4
- 229940117389 dichlorobenzene Drugs 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 150000005826 halohydrocarbons Chemical class 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 4
- 150000003462 sulfoxides Chemical class 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000254158 Lampyridae Species 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 3
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 3
- 239000000920 calcium hydroxide Substances 0.000 description 3
- 235000011116 calcium hydroxide Nutrition 0.000 description 3
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 238000003810 ethyl acetate extraction Methods 0.000 description 3
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- RRDQTXGFURAKDI-UHFFFAOYSA-N formaldehyde;naphthalene-2-sulfonic acid Chemical compound O=C.C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 RRDQTXGFURAKDI-UHFFFAOYSA-N 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 229920002114 octoxynol-9 Polymers 0.000 description 3
- 235000015320 potassium carbonate Nutrition 0.000 description 3
- 238000010298 pulverizing process Methods 0.000 description 3
- 238000007670 refining Methods 0.000 description 3
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 150000003457 sulfones Chemical class 0.000 description 3
- 125000003396 thiol group Chemical class [H]S* 0.000 description 3
- PBZUAIHRZUBBAJ-IWQZZHSRSA-N (2z)-2-hydroxyiminoacetic acid Chemical compound O\N=C/C(O)=O PBZUAIHRZUBBAJ-IWQZZHSRSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- XNMQEEKYCVKGBD-UHFFFAOYSA-N 2-butyne Chemical compound CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 2
- CAJGZJFXRJOICD-UHFFFAOYSA-N 3-chloro-5-ethyl-5-methyl-4h-1,2-oxazole Chemical compound CCC1(C)CC(Cl)=NO1 CAJGZJFXRJOICD-UHFFFAOYSA-N 0.000 description 2
- ZILNEOWOIBARRD-UHFFFAOYSA-N 5-methyl-4,5-dihydro-1,2-oxazole Chemical compound CC1CC=NO1 ZILNEOWOIBARRD-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 240000006122 Chenopodium album Species 0.000 description 2
- 235000009344 Chenopodium album Nutrition 0.000 description 2
- 244000285790 Cyperus iria Species 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 235000003990 Monochoria hastata Nutrition 0.000 description 2
- 240000000178 Monochoria vaginalis Species 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 244000292697 Polygonum aviculare Species 0.000 description 2
- 235000006386 Polygonum aviculare Nutrition 0.000 description 2
- 244000139819 Schoenoplectus juncoides Species 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- 229910052728 basic metal Inorganic materials 0.000 description 2
- 150000003818 basic metals Chemical class 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 238000009395 breeding Methods 0.000 description 2
- 230000001488 breeding effect Effects 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 235000012204 lemonade/lime carbonate Nutrition 0.000 description 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 2
- 239000000347 magnesium hydroxide Substances 0.000 description 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 2
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
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- 239000004202 carbamide Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
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- 229940126214 compound 3 Drugs 0.000 description 1
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- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
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- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
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- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
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- 229910052740 iodine Inorganic materials 0.000 description 1
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- 125000003971 isoxazolinyl group Chemical group 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
- 229920005610 lignin Polymers 0.000 description 1
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 229910001512 metal fluoride Inorganic materials 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- OPUAWDUYWRUIIL-UHFFFAOYSA-N methanedisulfonic acid Chemical compound OS(=O)(=O)CS(O)(=O)=O OPUAWDUYWRUIIL-UHFFFAOYSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
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- 235000009736 ragweed Nutrition 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 229960004249 sodium acetate Drugs 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/20—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings condensed with carbocyclic rings or ring systems
Abstract
本发明的异噁唑啉衍生物如通式[1]所示,式中,Q表示基团-S(O)n-(CR5R6)m-,n表示0~2的整数,m表示1~3的整数,R5和R6表示氢原子、氰基、烷氧羰基或C1~C6烷基等;R1和R2表示氢原子、可以被取代的烷基、烷氧羰基或可以被取代的苯基等;R3和R4表示氢原子、可以被取代的烷基或C3~C8环烷基等;Y表示氢原子、烷氧羰基、羧基、链烯基、可以被取代的烷基或可以被取代的苯基。本发明的除草剂含有该异噁唑啉衍生物作物有效成分。
Description
技术领域
本发明涉及新颖的异噁唑啉衍生物和含其为有效成分的除草剂。
背景技术
异噁唑啉衍生物具有除草活性,例如特开平8-225548号公报说明书、特开平9-328477号说明书和特开平9-328483号说明书中已有报道,但是,上述公报说明书记载的化合物多数在异噁唑啉环的5位上具有氯甲基,本发明的异噁唑啉衍生物尚属未知。
对有用作物所施用的除草剂,期望是在土壤或者茎叶上施用后,低药量下就显示充分的除草效果,而且是对作物·杂草具有高的选择性的药物。就此方面来说,目前的公报说明书中所记载的化合物还难以说可以满足要求。
发明的公开
本发明人等鉴于目前状况,在对除草效果和作物·杂草间选择性进行探讨的结果,发现新颖的异噁唑啉衍生物具有优良的除草效果和作物·杂草选择性,从而完成了本发明。
即,本发明提供了
式中,Q表示基团-S(O)n-(CR5R6)m-,n表示0~2的整数,m表示1~3的整数,R5和R6彼此独立表示氢原子、氰基、烷氧羰基或C1~C6烷基;
R1和R2表示氢原子、〔可以被C3~C8环烷基、C1~C6烷氧基、C1~C6烷基羰基、C1~C6烷硫基、C1~C6烷基亚磺酰基、C1~C6烷基磺酰基、C1~C6烷氨基、二(C1~C6烷基)氨基、羟基、氰基、C1~C6烷氧羰基、C1~C6烷基氨基羰基、二(C1~C6烷基)氨基羰基、(C1~C6烷硫基)羰基、羧基、(可以被取代的)苄氧基、(可以被取代的)苯氧基或(可以被取代的)苯基取代的〕C1~C8烷基、C3~C8环烷基、C1~C6烷氧羰基、C1~C6烷基氨基羰基、二(C1~C6烷基)氨基羰基、或(C1~C6烷硫基羰基、羧基或可以被取代的)苯基,或者R1和R2也可以与结合了上述基团的碳原子共同形成C3~C7螺环;
R3和R4表示氢原子、(可以被相同或不同的1~3个卤素原子、C3~C8环烷基或C1~C6烷氧基取代的)C1~C8烷基或C3~C8环烷基,R3和R4也可以与结合了上述基团的碳原子共同形成C3~C7螺环,或者R1、R2、R3和R4也可以与结合了上述基团的碳原子共同形成5~8员环;
Y表示氢原子、C1~C6烷氧羰基、羧基、C2~C6链烯基、〔可以被相同或不同的1~3个卤素原子、C1~C6烷氧基、C2~C6烯氧基、C2~C6炔氧基、(可以被取代的)苄氧基、C1~C6烷氧羰基、羧基、羟基或甲酰基取代的〕C1~C10烷基或(被1~5个相同或不同的R7取代的)苯基;
R7表示氢原子、〔可以被相同或不同的1~3个卤素原子、C1~C6烷氧基、羟基、C1~C6烷硫基、C1~C6烷基亚磺酰基、C1~C6烷基磺酰基、C1~C6烷基氨基、二(C1~C6)烷基氨基、氰基或(可以被取代的)苯氧基取代的〕C1~C6烷基、(可以被相同或不同的1~3个卤素原子、C1~C6烷氧基、C2~C6链烯基、C2~C6炔基、C1~C6烷氧羰基、C1~C6烷基羰基、C3~C8环烷基取代的)C1~C6烷氧基、C2~C6链烯基、C3~C8环烷氧基、(可以被相同或不同的1~3个卤素原子或C1~C6烷氧基取代的)C1~C6烷硫基、(可以被相同或不同的1~3个卤素原子或~C6烷氧基取代的)C1~C6烷基亚磺酰基、(可以被相同或不同的1~3个卤素原子或C1~C6烷氧基取代的)C1~C6烷基磺酰基、(可以被取代的)苄氧基、(可以被C1~C6烷基、C1~C6烷基磺酰基、C1~C6烷基羰基(C1~C6烷基)或C1~C6烷基磺酰基(C1~C6烷基)取代的)氨基、二(C1~C6烷基)氨基、卤素原子、氰基、硝基、C1~C6烷氧羰基、C3~C8环烷氧羰基、羧基、C2~C6烯氧羰基、C2~C6炔氧羰基、(可以被取代的)苄氧羰基、(可以被取代的)苯氧羰基或者C1~C6烷基羰氧基。
2.含有1记载的异噁唑啉衍生物或其盐作为有效成分的除草剂。实施发明的最佳方式
在本说明书中,所用用语的定义如下:
卤素原子是指氟原子、氯原子、溴原子或碘原子。
烷基,如果没有特别限定的话,指碳原子数1~10的直链或支链烷基,例如可举出甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、异戊基、新戊基、正己基、异己基、3,3-二甲丁基、庚基或辛基等。
环烷基是指碳原子数3~8的环烷基,例如可举出环丙基、环丁基、环戊基或环己基等。
烷氧基是指烷基部分具有以上含义的(烷基)-O-基团,例如可举出甲氧基或乙氧基等。
烷硫基、烷基亚磺酰基和烷基磺酰基是指烷基部分具有以上含义的(烷基)-S-基团、(烷基)-SO-基团、(烷基)-SO2-基团,例如可举出甲硫基、乙硫基、甲基亚磺酰基、甲磺酰基或乙基磺酰基等。
链烯基指碳原子数2~6的直链或支链的烯基,例如可举出乙烯基、1-丙烯基、2-丙烯基、异丙烯基、1-丁烯基、2-丁烯基、3-丁烯基或2-戊烯基等。
炔基是指碳原子数2~6的直链或支链的炔基,例如可举出乙炔基、2-丙炔基、2-丁炔基、3-丁炔基等。
烯氧基和炔氧基是指烯基或炔基部分具有以上含义的(烯基)-O-基团、(炔基)-O-基团,例如可举出2-丙烯氧基、2-丙炔氧基等。
烷基氨基和二烷基氨基是指烷基部分具有以上含义的(烷基)-NH-基团,(烷基)2N-基团,例如可举出甲氨基、乙氨基、二甲氨基等。
烷基羰基、(烷硫基)羰基、烷氧羰基、烷基氨基羰基和二烷基氨基羰基是指烷基、烷硫基、烷氧基、烷基氨基或二烷基氨基部分具有以上含义的烷基-CO-基团、(烷硫基)-CO-基团、烷氧基-CO-基团、烷基氨基-CO-基团和二烷基氨基-CO-基团,例如可举出乙酰基、甲硫基羰基、乙氧羰基、甲氧羰基、甲基氨基羰基、二甲基氨基羰基等。
烷基氨基羰基氨基、二烷基氨基羰基氨基和烷氧羰基氨基是指烷基氨基羰基、二烷基氨基羰基或烷氧羰基部分具有以上含义的(烷基氨基羰基)-NH-基团、(二烷基氨基羰基)-NH-基团和(烷氧羰基)-NH-基团,例如可举出甲基氨基羰基氨基、二甲氨基羰基氨基、甲氧羰基氨基等。
可以被取代的苯基可举出苯环上具有1~5个卤素原子、C1~C6烷基或C1~C6烷氧基等取代基的苯基。
可以被取代的苯氧基可举出苯环上具有1~5个卤素原子、C1~C6烷基或C1~C6烷氧基等取代基的苯氧基。
可以被取代的苄氧基可举出苯环或苯甲基位置上具有1~7个卤素原子、C1~C6烷基或C1~C6烷氧基等取代基的苄氧基。
可以被取代的苯氧羰基可举出苯环上具有1~5个卤素原子、C1~C6烷基或C1~C6烷氧基等取代基的苯氧羰基。
盐是指通式〔1〕表示的化合物中存在羧基、磺酰基羟基或氨基的情况下,上述基团与金属、有机碱、有机酸或无机酸所成的盐。作为金属可以举出钠或钾等碱金属或者镁或钙等碱土金属;作为有机碱可以举出三乙胺或二异丙胺等;作为有机酸可以举出醋酸、草酸、马来酸或对甲苯磺酸等;无机酸可以举出盐酸、硫酸或硝酸等。
上述通式〔1〕中,优选的化合物是R1和R2为碳1~3的烷基或碳1~3的烷氧基烷基、R3和R4是氢原子或碳1~3的烷基、Q是基团-S(O)n-(CR5R6)m-、R5和R6是氢原子或碳1~3的烷基、n是2、m是1、Y是(可以被取代的)苯基或碳2~10的烷基的化合物。
以下,通式〔1〕表示的本发明化合物的代表性化合物例如表1~表24所记载,不过本发明化合物并非限于此。化合物号参见以后的记载。
本说明书中,以下简写分别表示如下含义。
Me : 甲基 Et : 乙基
Pr : 正丙基 Pr-i : 异丙基
Pr-c : 环丙基 Bu : 正丁基
Bu-i : 异丁基 Bu-s : 仲丁基
Bu-t : 叔丁基 Bu-c : 环丁基
Pen : 正戊基 Hex : 正己基
Pen-c : 环戊基 Hex-c : 环己基
Ph : 苯基 Bn : 苄基
表2
化合物号 | R1 | R2 | R3 | R4 | Q | Y | 熔点(℃)或折射率(n D 20) |
1-211-221-231-241-251-261-271-281-291-301-311-321-331-341-351-361-371-381-391-401-411-421-431-441-45 | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | HHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHH | SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SCH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2 | Ph(3-Bu-i)Ph(4-Bu-i)Ph(2-Bu-s)Ph(3-Bu-s)Ph(4-Bu-s)Ph(2-Bu-t)Ph(3-Bu-t)Ph(4-Bu-t)Ph(2-Hex)Ph(3-Hex)Ph(4-Hex)Ph(2-F)Ph(3-F)Ph(4-F)Ph(2-Br)Ph(3-Br)Ph(4-Br)Ph(2,6-F2)Ph(2,6-F2)Ph(2-OMe)Ph(3-OMe)Ph(4-OMe)Ph(2-OEt)Ph(3-OEt)Ph(4-OEt) | 102-103105-105.5138-138.577-7877-80110-11194-9589-90122-12476-79 |
表3
化合物号 | R1 | R2 | R3 | R4 | Q | Y | 熔点(℃)或折射率(nD 20) |
1-461-471-481-491-501-511-521-531-541-551-561-571-581-591-601-611-621-631-641-651-661-671-681-691-70 | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | HHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHH | SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2 | Ph(2-OPr)Ph(3-OPr)Ph(4-OPr)Ph(2-OPr-i)Ph(3-OPr-i)Ph(4-OPr-i)Ph(2-OHex)Ph(3-OHex)Ph(4-OHex)Ph(2-OCHF2)Ph(3-OCHF2)Ph(4-OCHF2)Ph(2-OCF3)Ph(3-OCF3)Ph(4-OCF3)Ph(2-OCH2CH2OMe)Ph(3-OCH2CH2OMe)Ph(4-OCH2CH2OMe)Ph(2-SMe)Ph(3-SMe)Ph(4-SMe)Ph(2-SEt)Ph(3-SEt)Ph(4-SEt)Ph(2-SPr) | 67-6873-7480-8151-531.49282-84 |
表4
化合物号 | R1 | R2 | R3 | R4 | Q | Y | 熔点(℃)或折射率(nD 20) |
1-711-721-731-741-751-761-771-781-791-801-811-821-831-841-851-861-871-881-891-901-911-921-931-941-95 | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | HHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHH | SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2 | Ph(3-SPr)Ph(4-SPr)Ph(2-SBu)Ph(3-SBu)Ph(4-SBu)Ph(2-SHex)Ph(3-SHex)Ph(4-SHex)Ph(2-SCHF2)Ph(3-SCHF2)Ph(4-SCHF2)Ph(2-SCH2CH2OMe)Ph(3-SCH2CH2OMe)Ph(4-SCH2CH2OMe)Ph(2-SOMe)Ph(3-SOMe)Ph(4-SOMe)Ph(2-SOEt)Ph(3-SOEt)Ph(4-SOEt)Ph(2-SOPr)Ph(3-SOPr)Ph(4-SOPr)Ph(2-SOBu)Ph(3-SOBu) |
表5
化合物号 | R1 | R2 | R3 | R4 | Q | Y | 熔点(℃)或折射率(nD 20) |
1-961-971-981-991-1001-1011-1021-1031-1041-1051-1061-1071-1081-1091-1101-1111-1121-1131-1141-1151-1161-1171-1181-1191-120 | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | HHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHH | SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2 | Ph(4-SOBu)Ph(2-SOHex)Ph(3-SOHex)Ph(4-SOHex)Ph(2-SOCH2CF3)Ph(3-SOCH2CF3)Ph(4-SOCH2CF3)Ph(2-SOCH2CH2OMe)Ph(3-SOCH2CH2OMe)Ph(4-SOCH2CH2OMe)Ph(2-SO2Me)Ph(3-SO2Me)Ph(4-SO2Me)Ph(2-SO2Et)Ph(3-SO2Et)Ph(4-SO2Et)Ph(2-SO2Pr)Ph(3-SO2Pr)Ph(4-SO2Pr)Ph(2-SO2Bu)Ph(3-SO2Bu)Ph(4-SO2Bu)Ph(2-SO2Hex)Ph(3-SO2Hex)Ph(4-SO2Hex) | 97-98 |
表6
化合物号 | R1 | R2 | R3 | R4 | Q | Y | 熔点(℃)或折射率(nD 20) |
1-1211-1221-1231-1241-1251-1261-1271-1281-1291-1301-1311-1321-1331-1341-1351-1361-1371-1381-1391-1401-1411-1421-1431-1441-145 | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | HHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHH | SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2 | Ph(2-SO2CH2CH2OMe)Ph(3-SO2CH2CH2OMe)Ph(4-SO2CH2CH2OMe)Ph(2-SO2CH2CF3)Ph(3-SO2CH2CF3)Ph(4-SO2CH2CF3)Ph(2-CH2OPh)Ph(3-CH2OPh)Ph(4-CH2OPh)Ph(2-CH2OPh(2-Cl))Ph(3-CH2OPh(3-Me))Ph(4-CH2OPh(4-OMe))Ph(2-NHMe)Ph(3-NHMe)Ph(4-NHMe)Ph(2-N(Me)2)Ph(3-N(Me)2)Ph(4-N(Me)2)Ph(2-CN)Ph(3-CN)Ph(4-CN)Ph(2-NO2)Ph(3-NO2)Ph(4-NO2)Ph(2-CO2Me) | 120-122102-10397-98 |
表7
化合物号 | R1 | R2 | R3 | R4 | Q | Y | 熔点(℃)或折射率(nD 20) |
1-1461-1471-1481-1491-1501-1511-1521-1531-1541-1551-1561-1571-1581-1591-1601-1611-1621-1631-1641-1651-1661-1671-1681-1691-170 | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | HHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHH | SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2 | Ph(3-CO2Me)Ph(4-CO2Me)Ph(2-NHSO2Me)Ph(3-NHSO2Me)Ph(4-NHSO2Me)Ph(2-NHCH2COMe)Ph(3-NHCH2COMe)Ph(4-NHCH2COMe)Ph(2-NHCH2SO2Me)Ph(3-NHCH2SO2Me)Ph(4-NHCH2SO2Me)Ph(2-CF3)Ph(3-CF3)Ph(4-CF3)Ph(2-CH2OMe)Ph(3-CH2OMe)Ph(4-CH2OMe)Ph(2-CH2OH)Ph(3-CH2OH)Ph(4-CH2OH)Ph(2-CH2SMe)Ph(3-CH2SMe)Ph(4-CH2SMe)Ph(2-CH2SOMe)Ph(3-CH2SOMe) | 1.5009103-1041.5352 |
表8
化合物号 | R1 | R2 | R3 | R4 | Q | Y | 熔点(℃)或折射率(nD 20) |
1-1711-1721-1731-1741-1751-1761-1771-1781-1791-1801-1811-1821-1831-1841-1851-1861-1871-1881-1891-1901-1911-1921-1931-1941-195 | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeEtEtEtEtEtEtEtEt | HHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHH | SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2 | Ph(4-CH2SOMe)Ph(2-CH2SO2Me)Ph(3-CH2SO2Me)Ph(4-CH2SO2Me)Ph(2-CH2NHMe)Ph(3-CH2NHMe)Ph(4-CH2NHMe)Ph(2-CH2N(Me)2)Ph(3-CH2N(Me)2)Ph(4-CH2N(Me)2)Ph(2-CH2CN)Ph(3-CH2CN)Ph(4-CH2CN)Ph(2-F,3-Cl)Ph(2,6-Me2)Ph(2-OEt,3-Me)Ph(2-F,3-Me)PhPh(2-F)Ph(3-F)Ph(4-F)Ph(2-Cl)Ph(3-Cl)Ph(4-Cl)Ph(2-Br) | 128-130110-1121.523191-9238-3965-6758-5975-781.547267-6893-941.5289 |
表9
化合物号 | R1 | R2 | R3 | R4 | Q | Y | 熔点(℃)或折射率(nD 20) |
1-1961-1971-1981-1991-2001-2011-2021-2031-2041-2051-2061-2071-2081-2091-2101-2111-2121-2131-2141-2151-2161-2171-2181-2191-220 | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | EtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEt | HHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHH | SO2CH2SO2CH2SCH2SOCH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2 | Ph(3-Br)Ph(4-Br)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2-Me)Ph(3-Me)Ph(4-Me)Ph(2-Et)Ph(3-Et)Ph(4-Et)Ph(2-Pr)Ph(3-Pr)Ph(4-Pr)Ph(2-Pr-i)Ph(3-Pr-i)Ph(4-Pr-i)Ph(2-Bu)Ph(3-Bu)Ph(4-Bu)Ph(2-Bu-i)Ph(3-Bu-i)Ph(4-Bu-i)Ph(2-Bu-s)Ph(3-Bu-s) | 51-52<3064-651.537141-4243-44 |
表10
化合物号 | R1 | R2 | R3 | R4 | Q | Y | 熔点(℃)或折射率(nD 20) |
1-2211-2221-2231-2241-2251-2261-2271-2281-2291-2301-2311-2321-2331-2341-2351-2361-2371-2381-2391-2401-2411-2421-2431-2441-245 | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | EtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEt | HHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHH | SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CHXSO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2 | Ph(4-Bu-s)Ph(2-Bu-t)Ph(3-Bu-t)Ph(4-Bu-t)Ph(2-Hex)Ph(3-Hex)Ph(4-Hex)Ph(2-OMe)Ph(3-OMe)Ph(4-OMe)Ph(2-OEt)Ph(3-OEt)Ph(4-OEt)Ph(2-OPr)Ph(3-OPr)Ph(4-OPr)Ph(2-OPr-i)Ph(3-OPr-i)Ph(4-OPr-i)Ph(2-OHex)Ph(3-OHex)Ph(4-OHex)Ph(2-OCHF2)Ph(3-OCHF2)Ph(4-OCHF2) | 不可测定1.521972-74 |
表11
化合物号 | R1 | R2 | R3 | R4 | Q | Y | 熔点(℃)或折射率(nD 20) |
1-2461-2471-2481-2491-2501-2511-2521-2531-2541-2551-2561-2571-2581-2591-2601-2611-2621-2631-2641-2651-2661-2671-2681-2691-270 | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | EtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEt | HHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHH | SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2 | Ph(2-OCF3)Ph(3-OCF3)Ph(4-OCF3)Ph(2-OCH2CH2OMe)Ph(3-OCH2CH2OMe)Ph(4-OCH2CH2OMe)Ph(2-SMe)Ph(3-SMe)Ph(4-SMe)Ph(2-SEt)Ph(3-SEt)Ph(4-SEt)Ph(2-SPr)Ph(3-SPr)Ph(4-SPr)Ph(2-SBu)Ph(3-SBu)Ph(4-SBu)Ph(2-SHex)Ph(3-SHex)Ph(4-SHex)Ph(2-SCHF2)Ph(3-SCHF2)Ph(4-SCHF2)Ph(2-SCH2CH2OMe) |
表12
化合物号 | R1 | R2 | R3 | R4 | Q | Y | 熔点(℃)或折射率(nD 20) |
1-2711-2721-2731-2741-2751-2761-2771-2781-2791-2801-2811-2821-2831-2841-2851-2861-2871-2881-2891-2901-2911-2921-2931-2941-295 | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | EtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEt | HHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHH | SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2 | Ph(3-SCH2CH2OMe)Ph(4-SCH2CH2OMe)Ph(2-SOMe)Ph(3-SOMe)Ph(4-SOMe)Ph(2-SOEt)Ph(3-SOEt)Ph(4-SOEt)Ph(2-SOPr)Ph(3-SOPr)Ph(4-SOPr)Ph(2-SOBu)Ph(3-SOBu)Ph(4-SOBu)Ph(2-SOHex)Ph(3-SOHex)Ph(4-SOHex)Ph(2-SOCH2CF3)Ph(3-SOCH2CF3)Ph(4-SOCH2CF3)Ph(2-SOCH2CH2OMe)Ph(3-SOCH2CH2OMe)Ph(4-SOCH2CH2OMe)Ph(2-SO2Me)Ph(3-SO2Me) |
表13
化合物号 | R1 | R2 | R3 | R4 | Q | Y | 熔点(℃)或折射率(nD 20) |
1-2961-2971-2981-2991-3001-3011-3021-3031-3041-3051-3061-3071-3081-3091-3101-3111-3121-3131-3141-3151-3161-3171-3181-3191-320 | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | EtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEt | HHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHH | SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2 | Ph(4-SO2Me)Ph(2-SO2Et)Ph(3-SO2Et)Ph(4-SO2Et)Ph(2-SO2Pr)Ph(3-SO2Pr)Ph(4-SO2Pr)Ph(2-SO2Bu)Ph(3-SO2Bu)Ph(4-SO2Bu)Ph(2-SO2Hex)Ph(3-SO2Hex)Ph(4-SO2Hex)Ph(2-SO2CH2CF3)Ph(3-SO2CH2CF3)Ph(4-SO2CH2CF3)Ph(2-SO2CH2CH2OMe)Ph(3-SO2CH2CH2OMe)Ph(4-SO2CH2CH2OMe)Ph(2-OBn)Ph(3-OBn)Ph(4-OBn)Ph(2-OBn(2-Cl))Ph(2-OBn(3-Me))Ph(2-OBn(4-OMe)) |
表14
化合物号 | R1 | R2 | R3 | R4 | Q | Y | 熔点(℃)或折射率(nD 20) |
1-3211-3221-3231-3241-3251-3261-3271-3281-3291-3301-3311-3321-3331-3341-3351-3361-3371-3381-3391-3401-3411-3421-3431-3441-345 | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | EtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEt | HHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHH | SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2 | Ph(2-NHMe)Ph(3-NHMe)Ph(4-NHMe)Ph(2-N(Me)2)Ph(3-N(Me)2)Ph(4-N(Me)2)Ph(2-CN)Ph(3-CN)Ph(4-CN)Ph(2-NO2)Ph(3-NO2)Ph(4-NO2)Ph(2-CO2Me)Ph(3-CO2Me)Ph(4-CO2Me)Ph(2-CF3)Ph(3-CF3)Ph(4-CF3)Ph(2-CH2OMe)Ph(3-CH2OMe)Ph(4-CH2OMe)Ph(2-CH2OH)Ph(3-CH2OH)Ph(4-CH2OH)Ph(2-CH2SMe) | 83-8487-89115-1171.51521.5021 |
表15
化合物号 | R1 | R2 | R3 | R4 | Q | Y | 熔点(℃)或折射率(nD 20) |
1-3461-3471-3481-3491-3501-3511-3521-3531-3541-3551-3561-3571-3581-3591-3601-3611-3621-3631-3641-3651-3661-3671-3681-3691-370 | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeEtEtMeMeMeMeMeMe | EtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtPrPrPr-iPr-iMeMe | HHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHH | SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SOCH2SO2CH2SOCH2SO2CH2SOCH2SO2CH2SO2CH(Me)SO2CH(Me) | Ph(3-CH2SMe)Ph(4-CH2SMe)Ph(2-CH2SOMe)Ph(3-CH2SOMe)Ph(4-CH2SOMe)Ph(2-CH2SO2Me)Ph(3-CH2SO2Me)Ph(4-CH2SO2Me)Ph(2-CH2NHMe)Ph(3-CH2NHMe)Ph(4-CH2NHMe)Ph(2-CH2N(Me)2)Ph(3-CH2N(Me)2)Ph(4-CH2N(Me)2)Ph(2-CH2CN)Ph(3-CH2CN)Ph(4-CH2CN)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)PhPh(2,6-F2) | 63-6587-8944-4761-631.531962-63 |
表16
化合物号 | R1 | R2 | R3 | R4 | Q | Y | 熔点(℃)或折射率(nD 20) |
1-3711-3721-3731-3741-3751-3761-3771-3781-3791-3801-3811-3821-3831-3841-3851-3861-3871-3881-3891-3901-3911-3921-3931-3941-395 | MeMeMeMeMeMeMeMeMe | EtEtMeMeEtEtBnPr-cCH2Pr-c | HHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHH | SO2CH(Me)SO2CH(Me)SO2C(Me)2SO2C(Me)2SO2C(Me)2SO2C(Me)2SO2CH2SO2CH2SO2CH2SO2CH2SCH2SO2CH2SO2CH2SO2CH2SO2CH2SCH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SCH2SOCH2SO2CH2SCH2 | PhPh(2,6-F2)PhPh(2,6-F2)PhPh(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2) | 111-11349-51137-13893-95115-115.5113-114118-1201.55291.5342138-1391.51673-7580-84129-1311.5279 |
-(CH2)2--(CH2)3--(CH2)3--(CH2)4--(CH2)5- | |||||||
HHHHMeMeMeMeMeMeMe | -(CH2)3--(CH2)4--(CH2)4--(CH2)5- | ||||||
CH2CO2MeCH2CO2EtCH2CNCH2OHCH2OHCH2OHCH2OMe | HHHHHHH |
表17
化合物号 | R1 | R2 | R3 | R4 | Q | Y | 熔点(℃)或折射率(nD 20) |
1-3961-3971-3981-3991-4001-4011-4021-4031-4041-4051-4061-4071-4081-4091-4101-4111-4121-4131-4141-4151-4161-4171-4181-4191-420 | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | CH2OMeCH2OMeCH2OPh(2,6-Cl2)CH2OPh(2,6-Cl2)CH2OPh(2,6-Cl2)CH2OBn(2,6-F2)CH2SMeCH2SEtCH2SPrCH2SPr-iCH2SOMeCH2SOEtCH2SOPrCH2SOPr-iCH2NHMeCH2NHEtCH2NHEtCH2NHPrCH2NHPr-iCH2N(Me)2Bn(2-Me)Bn(3-OMe)Bn(4-Cl)CO2HCO2Me | HHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHH | SOCH2SO2CH2SCH2SOCH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SCH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SCH2SCH2 | Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2) | 1.5293105-1061.57151.56741.54611.52571.5268107-10875-76 |
表18
化合物号 | R1 | R2 | R3 | R4 | Q | Y | 熔点(℃)或折射率(nD 20) |
1-4211-4221-4231-4241-4251-4261-4271-4281-4291-4301-4311-4321-4331-4341-4351-4361-4371-4381-4391-4401-4411-4421-4431-4441-445 | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | CO2MeCO2MeCO2EtCO2PrCO2Pr-iCOSMeCOSEtCOSPrCOSPr-iCONHMeCONHEtCONHPrCONHPr-iCON(Me)2CON(Me)2CON(Me)2CON(Et)(Me)CON(Et)2CON(Pr)2PhPh(2-Me)Ph(3-OMe)Ph(4-Cl)Ph(4-Cl)Me | HHHHHHHHHHHHHHHHHHHHHHHHMe | HHHHHHHHHHHHHHHHHHHHHHHHMe | SOCH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SCH2SOCH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SOCH2SO2CH2SOCH2 | Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2) | 56-59115-1161.54231.54091.52361.5788100-101 |
表19
化合物号 | R1 | R2 | R3 | R4 | Q | Y | 熔点(℃)或折射率(nD 20) |
1-4461-4471-4481-4491-4501-4511-4521-4531-4541-4551-4561-4571-4581-4591-4601-4611-4621-4631-4641-4651-4661-4671-4681-4691-470 | MeHHMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | MeHHMeMeMeMeEtEtEtEtEtEtMeMeMeMeMeMeMeMeEtEtEtMe | MeMeMeHHHHHHHHHHHHHHHHHHHHHH | MeMeMeHHHHHHHHHHHHHHHHHHHHHH | SO2CH2SOCH2SO2CH2SO2CH(CO2Me)SO2CH(CN)SO2(CH2)2SO2(CH2)3SO2CH(CO2Me)SO2CH(CN)SO2(CH2)2SO2(CH2)2SO2(CH2)3SO2(CH2)3SO2CH2SO2CH2SO2CH2SCH2SO2CH2SO2CH2SO2CH2SO2CH2SCH2SO2CH2SCH2SO2CH2 | Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)PhPhPh(2,6-F2)CF3CH2CF3CH2OHCH2OHCH2OMeCH2OHexCH2OCH2CH=CH2CH2OBnCO2HCH2CO2MeCH2CO2MeCH2CO2Me | 63-641.51611.50881.48521.4919 |
表20
化合物号 | R1 | R2 | R3 | R4 | Q | Y | 熔点(℃)或折射率(nD 20) |
1-4711-4721-4731-4741-4751-4761-4771-4781-4791-4801-4811-4821-4831-4841-4851-4861-4871-4881-4891-4901-4911-4921-4931-4941-495 | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | MeMeMeMeEtEtEtEtEtEtEtEtEtEtEtEtMeMeMeMeMeMe | HHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHH | SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SCH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2 | CH2CO2HCH2OHCH2CHOCH=CH2CF3CH2CF3CH2OHCH2OHCH2OMeCH2OHexCH2OCH2CH=CH2CH2OBnCH2CO2MeCH2CO2HexCH2OHCH2CHOPh(2,3-Cl2)Ph(2,4-Cl2)Ph(2,5-Cl2)Ph(2,6-Cl2)Ph(3,4-Cl2)Ph(3,5-Cl2)Ph(2,6-F2)Ph(2-Cl,6-F)Ph(2,6-F2) | 1.5088128-129122-123123-124153-154121-122103-10495-97108-1091.5183 |
-(CH2)4- | |||||||
MeMe | HMe |
表21
化合物号 | R1 | R2 | R3 | R4 | Q | Y | 熔点(℃)或折射率(nD 20) |
1-4961-4971-4981-4991-5001-5011-5021-5031-5041-5051-5061-5071-5081-5091-5101-5111-5121-5131-5141-5151-5161-5171-5181-5191-520 | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeHHPr-c | HMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | MeHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHH | SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2 | Ph(2,6-F2)Ph(3,4-F2)Ph(2,5-F2)Ph(2-F,6-NO2)Ph(2,4,6-F3)Ph(2,3,6-F3)Ph(2,6-Et2)Ph(2-NO2,3-CO2Me)Ph(2,3-F2)Ph(2,4-F2)Ph(3,5-F2)Ph(2,3,4-F3)Ph(2,3,5-F3)Ph(3,4,5-F3)Ph(2,4,5-F3)Ph(2,4-Me2)Ph(2,5-Me2)Ph(3,4-Me2)Ph(2-F,5-CF3)Ph(2-F,3-CF3)Ph(2-F,4-Br)Ph(2-SO2CF3)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2) | 64-65109-110107-108146-14787-88136-13850-53112-114124-125104-105139-140100-103105-107150-151124-1261.542165-6662-6595-97109-111123-12580-8165-6697-9995-96 |
-(CH2)5--(CH2)6- | |||||||
Pr-c | H |
表22
化合物号 | R1 | R2 | R3 | R4 | Q | Y | 熔点(℃)或折射率(nD 20) |
1-5211-5221-5231-5241-5251-5261-5271-5281-5291-5301-5311-5321-5331-5341-5351-5361-5371-5381-5391-5401-5411-5421-5431-5441-545 | MeMeMeMeMeMeMeMeMeMeMeMeHMeMeMeMeMeMeMeMeMeMeMeMe | MeMeMeMeMeMeMeMeMeMeMeHHMeMeMeMeMeMeMeMeMeMeMeMe | HHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHH | SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2 | Ph(2-I)Ph(2,3-Me2)Ph(3,5-Me2)Ph(3,5-OMe2)Ph(2-Et,6-Me)Ph(2-OEt,6-F)Ph(2-F,6-CF3)Ph(2-F,4-CF3)Ph(2,4,6-Me3)Ph(2-OMe,5-NO2)Ph(2,3,4,5,6-F5)Ph(2,6-F2)Ph(2,6-F2)Ph(2-F,6-OMe)Ph(2,6-OMe2)Ph(2,6-OEt2)Ph(2-Me,3-NO2)Ph(2-Cl,4-F)Ph(4-Cl,2-NO2)Ph(5-Me,2-NO2)Ph(4-F,3-CF3)Ph(3-F,5-CF3)Ph(3,5-(CF3)2)Ph(2,5-(CF3)2)Ph(3,5-Br2) | 70-72123-12497-98125-1261.54141.525189-90124-125119-120125-126113-114126-127125-126125-127165-16785-88109-11192-93136-137124-12599-10187-89130-132100-103115-116 |
表23
化合物号 | R1 | R2 | R3 | R4 | Q | Y | 熔点(℃)或折射率(nD 20) |
1-5461-5471-5481-5491-5501-5511-5521-5531-5541-5551-5561-5571-5581-5591-5601-5611-5621-5631-5641-5651-5661-5671-5681-5691-570 | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | MeMeMeMeMeMeMeMeMeMe | HHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHH | SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2 | Ph(3,5-(NO2)2)Ph(2,3,5,6-(Me)4)Ph(2-F,6-1)Ph(2-NH2,6-F)Ph(2,6-F2,3-Me)Ph(4-F,2-CF3)Ph(2-NH2)Ph(2-Br,6-F)Ph(2,6-Br2)Ph(2-F,6-CO2Me)Ph(2,6-F2)Ph(2-F,6-NMe2)Ph(2-F,6-NEt2)Ph(2-OCH2C≡CH)Ph(2-Cl,6-Me)Ph(2-Cl,6-OCHF2)Ph(2-OCHF2)Ph(2-Cl,6-OMe)Ph(2-Cl,6-OEt)Ph(2-Cl,6-OPr-n)Ph(2-Cl,6-OPr-i)Ph(2-Cl,6-OCH2CF3)Ph(2-OBu-n)Ph(2-F,6-OPr-n)Ph(2-F,6-OPr-i) | 162-163128-130137-138118-121118-11950-51107-109126-127158-160103-10586-87108-11090-92110-11398-10083-841.5215128-12965-6766-681.540292-9550-5174-76.51.5139 |
-(CH2)5- | |||||||
MeMeMeMeMePr-cMeMeMeMeMeMeMeMe | HHHHHHHHHHHHHH |
表24
化合物号 | R1 | R2 | R3 | R4 | Q | Y | 熔点(℃)或折射率(nD 20) |
1-5711-5721-5731-5741-5751-5761-5771-5781-5791-5801-5811-5821-5831-5841-5851-5861-5871-5881-5891-5901-5911-5921-5931-5941-595 | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | HHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHH | SO2CH2SO2CH2SO2CH2SO2CH2SO2CH(Me)SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH(Me)SCH(Me)SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2 | Ph(2-F,6-OBu-n)Ph(2-Cl,6-OBu-i)Ph(2-F,6-OCHF2)Ph(2-Cl,6-OBu-n)Ph(2-CF3)Ph(2-F,6-OCH2C≡CH)Ph(2-OCH2CO2Me)Ph(2-OCH2CO2Et)Ph(2-O(CH2)2OMe)Ph(2-O(CH2)2OEt)PhPhPh(2-Me,6-MeO)Ph(2-Me,3-Pr-i,6-MeO)Ph(2-OEt,6-CF3)Ph(2-CH2OEt)Ph(2-OCOMe)Ph(2-OCH2Ph)Ph(2-OCH2CH=CH2)Ph(2-Cl,6-OCH2CH-CH)Ph(2-Cl,6-OCH2C≡CH)Ph(2-CO2H)Ph(2-CO2Et)Ph(2-CO2Pr-n)Ph(2-CO2Pr-i) | 74-7592-941.496165-671.4965102-105110-11192-931.50891.4991120-12159-6092-93108-10988-891.531887-89120-12371-73不可测定108-111182-1841.53321.52941.5252 |
表25
化合物号 | R1 | R2 | R3 | R4 | Q | Y | 熔点(℃)或折射率(nD 20) |
1-5961-5971-5981-5991-6001-6011-6021-6031-6041-6051-6061-6071-6081-6091-6101-6111-6121-6131-6141-6151-6161-6171-6181-6191-620 | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeEtMeMeMe | HHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHH | SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2 | Ph(2-CO2Bu-n)Ph(2-CO2Bu-s)Ph(2-CO2Bu-i)Ph(2-CO2CH2CH-CH2)Ph(2-CO2CH2C≡CH)Ph(2-CO2Pen-c)Ph(2-OEt,6-Me)Ph(2-OPr-n,6-Me)Ph(2-OPr-i,6-Me)Ph(2-OBu-n,6-Me)Ph(2-Me,6-OCH2CH-CH)Ph(2-Me,6-OCH2C≡CH)Ph(2-OCH2Pr-c)Ph(2-OPen-c)Ph(2-OHex-c)Ph(2-CO2CH2Ph)Ph(2-CO2CH2Ph(2-Cl))Ph(2-CO2CH2Ph(3-Cl))Ph(2-CO2CH2Ph(4-Cl))Ph(2-CH2OBu-n)Ph(2,3,6-Me3)Ph(2,3,6-Me3)Ph(2-Cl,6-CO2Me)Ph(2-Cl,6-CO2Et)Ph(2-Cl,6-CO2Pr-n) | 1.52621.522364-65不可测定90-9178-79不可测定不可测定1.5364不可测定不可测定不可测定1.53791.54091.539996-971.56311.56611.564242-4397-9968-70136-137108-10976-77 |
表26
化合物号 | R1 | R2 | R3 | R4 | Q | Y | 熔点(℃)或折射率(nD 20) |
1-6211-6221-6231-6241-6251-6261-6271-6281-6291-6301-6311-6321-6331-6341-6351-6361-6371-6381-6391-6401-6411-6421-6431-6441-645 | MeMeMeMeMeMeMeMeHHHMeMeMeMeMeMeMeMeMeMeMeMeMeMe | MeMeMeMeMeMeMeMeCON(Et)2CON(Et)2CON(Et)2MeMeMeMeMeMeMeMeMeMeMeMeMeMe | HHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHH | SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SCH2SOCH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2 | Ph(2-Cl,6-CO2Pr-i)Ph(2-Cl,6-CO2Bu-n)Ph(2-Cl,6-CO2Bu-s)Ph(2-Cl,6-CO2Bu-i)Ph(2-Cl,6-CO2CH2Ph)Ph(2-Cl,6-CO2Ph(2-Cl))Ph(2-Cl,6-CO2CHPh(3-Cl)Ph(2-Cl,6-CO2CHPh(4-Cl))Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2-Cl,5-OMe)Ph(2-Cl,5-OEt)Ph(2-Cl,5-OPr-n)Ph(2-Cl,5-OPr-i)Ph(2-Cl,5-OBu-n)Ph(2-Cl,5-OCH2CH-CH2)Ph(2-Cl,5-OCH2C≡CH)Ph(2-Et,6-OMe)Ph(2-Cl,6-CO2H)Ph(2-F,6-CO2H)Ph(2-F,6-CO2Et)Ph(2-F,6-CO2Pr-n)Ph(2-F,6-CO2Pr-i)Ph(2-F,6-CO2Bu-n) | 114-11594-9594-9799-100121-122111-11282-83111-1121.53721.53741.512292-93114-11595-9664-6587-8866-6791-9278-79176-176.5176-17767-6855-5692-9394-95 |
表27
化合物号 | R1 | R2 | R3 | R4 | Q | Y | 熔点(℃)或折射率(nD 20) |
1-6461-6471-6481-6491-6501-6511-6521-6531-6541-6551-6561-6571-6581-6591-6601-6611-6621-6631-6641-6651-6661-6671-6681-6691-670 | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | MeMeMeMeMeMeEtMeMeMeMeMeMeMeEtMeEtMeEtMeEtMeMeMeEt | HHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHH | SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2 | Ph(2-F,6-CO2Bu-s)Ph(2-F,6-CO2Bu-i)Ph(2-F,6-CO2CH2Ph)Ph(2-F,6-CO2CH2Ph(2-Cl))Ph(2-F,6-CO2CH2Ph(3-Cl))Ph(2-F,6-CO2CH2Ph(4-Cl))Ph(2,3,5,6-(Me)4)Ph(2-OEt,6-Et)Ph(2-OPr-n,6-Et)Ph(2-OPr-i,6-Et)Ph(2-OBu-n,6-Et)Ph(2-OCH2Ch=Ch2,6-Et)Ph(2-OCH2C≡CH,6-Et)Ph(2,3,5,6-F4)Ph(2,3,5,6-F4)Ph(2-CO2Me,3-Me)Ph(2-CO2Me,3-Me)Ph(2-CO2Et,3-Me)Ph(2-CO2Et,3-Me)Ph(2-CO2Bu-i,3-Me)Ph(2-CO2Bu-i,3-Me)Ph(2,5-Me2,6-OMe)Ph(2,5-Me2,6-OEt)Ph(2,5-Me2,6-OPr-n)Ph(2,3,5,6-(Me)4) | 49-5086-87191-19289-9089-90108-10994-9588-901.53211.531243-451.5451.5489129-131110-11259-611.52921.5192117-1181.530975-76 |
表28
化合物号 | R1 | R2 | R3 | R4 | Q | Y | 熔点(℃)或折射率(nD 20) |
1-6711-6721-6731-6741-6751-6761-6771-6781-6791-6801-6811-6821-6831-6841-6851-6861-6871-6881-6891-6901-6911-6921-6931-6941-695 | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | MeMeMeMeMeMeMeMeMeCH2CO2HCH2COEtCH2COMeCH2CON(Et)2CH2CON(Me)2CH2CONHEtCH2CONHMeCH2COSEtCH2COSMeCH2OPhCH2OPh(2-Me)CH2OPh(2-OMe)CH2OPh(3-Me)CH2OPh(3-OMe)CH2OPh(4-Me)CH2OPh(4-OMe) | HHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHH | SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SCH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2 | Ph(2,3,5-(Me)3,6-OMe)Ph(2,3,5-(Me)3,6-OEt)Ph(2,3,5-(Me)3,6-OPr-n)Ph(2,3,5-(Me)3,6-OPr-i)Ph(2,5-(Me)2,3,6-Cl2)Ph(2,5-(Me)2,3,6-Br2)Ph(2,3,6-(Me)3,5-Cl)Ph(2,3,6-(Me)3,5-Br)PhPh(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2) | 1.5521 |
表29
化合物号 | R1 | R2 | R3 | R4 | Q | Y | 熔点(℃)或折射率(nD 20) |
1-6961-6971-6981-6991-7001-7011-7021-7031-7041-7051-7061-7071-7081-7091-7101-7111-7121-7131-7141-7151-7161-7171-7181-7191-720 | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | CH2SO2EtCH2SO2MeEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEt | HHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHH | SO2CH2SO2CH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SOxCH2 | Ph(2,6-F2)Ph(2,6-F2)Ph(2,3,4,5,6-(Me)5)Ph(2,3,5-(Me)3)PH(2,3,5-(Me)3,6-OCHCP)Ph(2,3,5-(Me)3,6-OCHF2)Ph(2,3,5-(Me)3,6-OEt)Ph(2,3,5-(Me)3,6-OMe)Ph(2,3,5-(Me)3,6-OPr-i)Ph(2,3,5-(Me)3,6-OPr-n)Ph(2,3,6-(Me)3,5-Br)Ph(2,3,6-(Me)3,5-Cl)Ph(2,3,6-(Me)3,5-F)Ph(2,3,6-(Me)3,5-I)Ph(2,5-(Me)2,3,6-Br2)Ph(2,5-(Me)2,3,6-Cl2)Ph(2,3,4,5,6-(Me)5)Ph(2,3,5-(Me)3)Ph(2,3,5-(Me)3,6-OCH2CP)Ph(2,3,5-(Me)3,6-OCHF2)Ph(2,3,5-(Me)3,6-OEt)Ph(2,3,5-(Me)3,6-OMe)Ph(2,3,5-(Me)3,6-OPr-i)Ph(2,3,5-(Me)3,6-OPr-n)Ph(2,3,6(Me)3,5-Br) |
表30
化合物号 | R1 | R2 | R3 | R4 | Q | Y | 熔点(℃)或折射率(nD 20) |
1-7211-7221-7231-7241-7251-7261-7271-7281-7291-7301-7311-7321-7331-7341-7351-7361-7371-7381-7391-7401-7411-7421-7431-7441-745 | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | EtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtEtMeMeMeMeMeMe | HHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHH | SO2CH2SO2CH2SO2CHxSO2CH2SO2CH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SCH2SCH2SCH2SCH2SCH2SCH2 | Ph(2,3,6-(Me)3,5-Cl)Ph(2,3,6-(Me)3,5-F)Ph(2,3,6-(Me)3,5-I)Ph(2,5-(Me)2,3,6-Br2)Ph(2,5-(Me)2,3,6-Cl2)Ph(2,3,4,5,6-(Me)5)Ph(2,3,5-(Me)3)Ph(2,3,5-(Me)3,6-OCH2CP)Ph(2,3,5-(Me)3,6-OCHF2)Ph(2,3,5-(Me)3,6-OEt)Ph(2,3,5-(Me)3,6-OMe)Ph(2,3,5-(Me)3,6-OP-i)Ph(2,3,5-(Me)3,6-OPr-n)Ph(2,3,6-(Me)3,5-Br)Ph(2,3,6-(Me)3,5-Cl)Ph(2,3,6-(Me)3,5-F)Ph(2,3,6-(Me)3,5-I)Ph(2,5-(Me)2,3,6-Br2)Ph(2,5-(Me)2,3,6-Cl2)Ph(2,3,4,5,6-(Me)5)Ph(2,3,5-(Me)3)Ph(2,3,5-(Me)3,6-OCH2CP)Ph(2,3,5-(Me)3,6-OCHF2)Ph(2,3,5-(Me)3,6-OEt)Ph(2,3,5-(Me)3,6-OMe) |
表31
化合物号 | R1 | R2 | R3 | R4 | Q | Y | 熔点(℃)或折射率(nD 20) |
1-7461-7471-7481-7491-7501-7511-7521-7531-7541-7551-7561-7571-7581-7591-7601-7611-7621-7631-7641-7651-7661-7671-7681-7691-770 | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | HHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHH | SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2 | Ph(2,3,5-(Me)3,6-OPr-i)Ph(2,3,5-(Me)3,6-OPr-n)Ph(2,3,5,6-(Me)4)Ph(2,3,6-(Me)3,5-Br)Ph(2,3,6-(Me)3,5-Cl)Ph(2,3,6-(Me)3,5-F)Ph(2,3,6-(Me)3,5-I)Ph(2,3-Me2)Ph(2,4-Me2)Ph(2,5-(Me)2,3,6-Br2)Ph(2,5-(Me)2,3,6-Cl2)Ph(2,5-Me2)Ph(2,6-Me2)Ph(2-Br)Ph(2-Bu)Ph(2-Bu-i)Ph(2-Bu-s)Ph(2-Bu-t)Ph(2-CF3)Ph(2-Cl)Ph(2-Et)Ph(2-F)Ph(2-Hex)Ph(2-Me)Ph(2-OCF3) |
表32
化合物号 | R1 | R2 | R3 | R4 | Q | Y | 熔点(℃)或折射率(nD 20) |
1-7711-7721-7731-7741-7751-7761-7771-7781-7791-7801-7811-7821-7831-7841-7851-7861-7871-7881-7891-7901-7911-7921-7931-7941-795 | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | HHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHH | SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2 | Ph(2-OCHF2)Ph(2-OEt)Ph(2-OHex)Ph(2-OMe)Ph(2-OPr)Ph(2-OPr-i)Ph(2-Pr)Ph(2-Pr-i)Ph(3,4-Me2)Ph(3,5-Me2)Ph(3-Br)Ph(3-Bu)Ph(3-Bu-i)Ph(3-Bu-s)Ph(3-Bu-t)Ph(3-CF3)Ph(3-Cl)Ph(3-Et)Ph(3-F)Ph(3-Hex)Ph(3-Me)Ph(3-OCF3)Ph(3-OCHF2)Ph(3-OEt)Ph(3-OHex) |
表33
化合物号 | R1 | R2 | R3 | R4 | Q | Y | 熔点(℃)或折射率(nD 20) |
1-7961-7971-7981-7991-8001-8011-8021-8031-8041-8051-8061-8071-8081-8091-8101-8111-8121-8131-8141-8151-8161-8171-8181-8191-820 | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | HHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHH | SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2SCH2 | Ph(3-OMe)Ph(3-OPr)Ph(3-OPr-i)Ph(3-Pr)Ph(3-Pr-i)Ph(4-Br)Ph(4-Bu)Ph(4-Bu-i)Ph(4-Bu-s)Ph(4-Bu-t)Ph(4-CF3)Ph(4-Cl)Ph(4-Et)Ph(4-F)Ph(4-Hex)Ph(4-Me)Ph(4-OCF3)Ph(4-OCHF2)Ph(4-OEt)Ph(4-OHex)Ph(4-OMe)Ph(4-OPr)Ph(4-OPr-i)Ph(4-Pr)Ph(4-Pr-i) |
表34
化合物号 | R1 | R2 | R3 | R4 | Q | Y | 熔点(℃)或折射率(nD 20) |
1-8211-8221-8231-8241-8251-8261-8271-8281-8291-8301-8311-8321-8331-8341-8351-8361-8371-8381-8391-8401-8411-8421-8431-8441-845 | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | HHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHH | SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2 | Ph(2,3,4,5,6-(Me)5)Ph(2,3,5-(Me)3)Ph(2,3,5-(Me)3,6-CH2CP)Ph(2,3,5-(Me)3,6-OCHF2)Ph(2,3,6-(Me)3,5-F)Ph(2,3,6-(Me)3,5-I)Ph(2,3,4,5,6-(Me)5)Ph(2,3,5-(Me)3)Ph(2,3,5-(Me)3,6-OCH2CP)Ph(2,3,5-(Me)3,6-OCHF2)Ph(2,3,5-(Me)3,6-OEt)Ph(2,3,5-(Me)3,6-OMe)Ph(2,3,5-(Me)3,6-OPr-i)Ph(2,3,5-(Me)3,6-OPr-n)Ph(2,3,5,6-(Me)4)Ph(2,3,6-(Me)3,5-Br)Ph(2,3,6-(Me)3,5-Cl)Ph(2,3,6-(Me)3,5-F)Ph(2,3,6-(Me)3,5-l)Ph(2,3-Me2)Ph(2,4-Me2)Ph(2,5-(Me)2,3,6-Br2)Ph(2,5-(Me)2,3,6-Cl2)Ph(2,5-Me2)Ph(2,6-Me2) |
表35
化合物号 | R1 | R2 | R3 | R4 | Q | Y | 熔点(℃)或折射率(nD 20) |
1-8461-8471-8481-8491-8501-8511-8521-8531-8541-8551-8561-8571-8581-8591-8601-8611-8621-8631-8641-8651-8661-8671-8681-8691-870 | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | HHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHH | SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2 | Ph(2-Br)Ph(2-Bu)Ph(2-Bu-i)Ph(2-Bu-s)Ph(2-Bu-t)Ph(2-CF3)Ph(2-Cl)Ph(2-Et)Ph(2-F)Ph(2-Hex)Ph(2-Me)Ph(2-OCF3)Ph(2-OCHF2)Ph(2-OEt)Ph(2-OHex)Ph(2-OMe)Ph(2-OPr)Ph(2-OPr-i)Ph(2-Pr)Ph(2-Pr-i)Ph(3,4-Me2)Ph(3,5-Me2)Ph(3-Br)Ph(3-Bu)Ph(3-Bu-i) |
表36
化合物号 | R1 | R2 | R3 | R4 | Q | Y | 熔点(℃)或折射率(nD 20) |
1-8711-8721-8731-8741-8751-8761-8771-8781-8791-8801-8811-8821-8831-8841-8851-8861-8871-8881-8891-8901-8911-8921-8931-8941-895 | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | HHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHH | SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2 | Ph(3-Bu-s)Ph(3-Bu-t)Ph(3-CF3)Ph(3-Cl)Ph(3-Et)Ph(3-F)Ph(3-Hex)Ph(3-Me)Ph(3-OCF3)Ph(3-OCHF2)Ph(3-OEt)Ph(3-OHex)Ph(3-OMe)Ph(3-OPr)Ph(3-OPr-i)Ph(3-Pr)Ph(3-Pr-i)Ph(4-Br)Ph(4-Bu)Ph(4-Bu-i)Ph(4-Bu-s)Ph(4-Bu-t)Ph(4-CF3)Ph(4-Cl)Ph(4-Et) |
表37
化合物号 | R1 | R2 | R3 | R4 | Q | Y | 熔点(℃)或折射率(nD 20) |
1-8961-8971-8981-8991-9001-9011-9021-9031-9041-9051-9061-9071-9081-9091-9101-9111-9121-9131-9141-9151-9161-9171-9181-9191-920 | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | HHHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHCH2Pr-cCH2CF3CH2OMeCH2Pr-cCH2CF3CH2OMeCH2Pr-cCH2CF3CH2OMePr-cPr-cPr-cH | SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SO2CH2SO2CH2SO2CH2SOCH2SOCH2SOCH2SCH2SCH2SCH2SCH2SOCH2SO2CH2SO2CH2 | Ph(4-F)Ph(4-Hex)Ph(4-Me)Ph(4-OCF3)Ph(4-OCHF2)Ph(4-OEt)Ph(4-OHex)Ph(4-OMe)Ph(4-OPr)Ph(4-OPr-i)Ph(4-Pr)Ph(4-Pr-i)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)Ph(2,6-F2)CH2OCH2C≡CH |
表38
化合物号 | R1 | R2 | R3 | R4 | Q | Y | 熔点(℃)或折射率(nD 20) |
1-9211-9221-9231-9241-9251-9261-9271-9281-9291-9301-9311-9321-9331-9341-9351-9361-9371-9381-9391-9401-941 | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | MeMeMeMeMeMeEtEtEtMeMeMeEtEtEtMeMeMeEtEtEt | HHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHHHHHHHH | SO2CH2SO2CH2SO2CH2SCH2SCH2SCH2SCH2SCH2SCH2SOCH2SOCH2SOCH2SOCH2SOCH2SOCH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2SO2CH2 | Ph(2-OC2H4CO2Me)Ph(2-OC2H4COMe)Ph(2-CO2Ph)Ph(2,3,5-(Me)3,6-F)Ph(2,3,5-(Me)3,6-Cl)Ph(2,3,5-(Me)3,6-Br)Ph(2,3,5-(Me)3,6-F)Ph(2,3,5-(Me)3,6-Cl)Ph(2,3,5-(Me)3,6-Br)Ph(2,3,5-(Me)3,6-F)Ph(2,3,5-(Me)3,6-Cl)Ph(2,3,5-(Me)3,6-Br)Ph(2,3,5-(Me)3,6-F)Ph(2,3,5-(Me)3,6-Cl)Ph(2,3,5-(Me)3,6-Br)Ph(2,3,5-(Me)3,6-F)Ph(2,3,5-(Me)3,6-Cl)Ph(2,3,5-(Me)3,6-Br)Ph(2,3,5-(Me)3,6-F)Ph(2,3,5-(Me)3,6-Cl)Ph(2,3,5-(Me)3,6-Br) |
通式〔1〕表示的本发明化合物可以按照以下所示制备方法制备,不过并非限于此。
式中,L表示卤素原子、对甲苯磺酰基之类的可以被C1~C4烷基取代的苯磺酰基或甲磺酰基之类的C1~C4烷基磺酰基等离去基团(优选氯原子),R1、R2、R3、R4、R5、R6、Y和m含义同前。
以下详细说明上述制备方法的各步骤。
(步骤1)
通式〔II〕表示的化合物,与通式〔III〕表示的巯基衍生物在适当溶剂中或无溶剂存在下(优选在适当溶剂中)、在碱的存在下反应,或者通式〔III〕表示的巯基衍生物的盐(在此指钠盐或者钾盐)在适当溶剂中反应,可以获得通式〔IV〕表示的目标硫醚衍生物。
在此作为溶剂例如有二乙醚、二甲氧基乙烷、二氧六环、或四氢呋喃(THF)等醚,二氯甲烷、氯仿、四氯化碳、二氯乙烷、氯代苯或二氯代苯等卤代烃,N,N-二甲基乙酰胺、N,N-二甲基甲酰胺(DMF)或N-甲基-2-吡咯烷酮等酰胺,二甲亚砜(DMSO)或环丁砜等硫化合物,苯、甲苯或二甲苯等芳香烃,甲醇、乙醇、丙醇、异丙醇、丁醇或叔丁醇等醇,丙酮或2-丁酮等酮,乙腈等腈,水或上述的混合物。
另外,碱如氢化钠等金属氢化合物,氨基钠或二异丙氨基锂等碱金属胺化物,吡啶、三乙胺或1,8-二氮杂二环〔5.4.0〕-7-十一烯等有机碱,氢氧化钠、氢氧化钾等碱金属氢氧化物,氢氧化钙或氢氧化镁等碱土金属氢氧化物,碳酸钠或碳酸钾等碱金属碳酸盐,碳酸氢钠或碳酸氢钾等碱金属碳酸氢盐等无机碱或者甲醇钠或叔丁醇钾等金属醇盐。
反应温度可以在0℃到反应体系的回流温度的任意温度下进行,优选10℃~100℃,反应因化合物而异,0.5~24小时结束。
(步骤2)
通式〔IV〕所示的硫醚衍生物的氧化反应是使通式〔IV〕所示的硫醚衍生物与氧化剂(例如间氯过苯甲酸、过氧甲酸或过氧乙酸等有机过氧化物,过氧化氢、高锰酸钾或高碘酸钠等无机过氧化物)在适当的溶剂中反应,可以获得通式〔V〕所示的亚砜衍生物。
在此作为溶剂例如有二氯甲烷、氯仿、二氯乙烷、四氯化碳、氯代苯或二氯代苯等卤代烃,二氧六环、四氢呋喃(THF)、二甲氧基乙烷或二乙醚等醚,N,N-二甲基乙酰胺、N,N-二甲基甲酰胺(DMF)或N-甲基-2-吡咯烷酮等酰胺,甲醇、乙醇、丙醇、异丙醇、丁醇或叔丁醇等醇,丙酮或2-丁酮等酮,乙腈等腈,醋酸,水或上述的混合物等。
反应温度可以在0℃到反应体系的回流温度的任意温度下进行,优选10℃~60℃,反应因化合物而异,1~72小时结束。
(步骤3)
通式〔V〕表示的亚砜衍生物与氧化剂(同步骤2所记载者)在适当的溶剂(同步骤2所记载者)中反应,可以获得通式〔VI〕所示的砜衍生物。
反应温度可以在0℃到反应体系的回流温度的任意温度下进行,优选10℃~60℃,反应因化合物而异,1~72小时结束。
(步骤4)
通式〔IV〕所示的硫醚衍生物的氧化反应中,采用适当量的氧化剂,可以无需分离出通式〔V〕所示的亚砜衍生物而获得通式〔VI〕所示的砜衍生物。
即,通式〔IV〕所示的硫醚衍生物与氧化剂(同步骤2所述)在适当溶剂(同步骤2所述)中反应,可以获得通式〔V〕所示的目标亚砜衍生物。
反应温度可以在0℃到反应体系的回流温度的任意温度下进行,优选10℃~60℃,反应因化合物而异,1~72小时结束。
通式〔II〕所示的化合物中,L表示卤素原子的化合物可以按照步骤5所示的方法合成。
式中,X1表示卤素原子(优选氯原子),R1、R2、R3和R4含义同前。
即,通式〔VIII〕所示的化合物与通式〔VII〕所示的烯烃衍生物在适当溶剂中或无溶剂存在下(优选在适当溶剂中)、在碱的存在下反应,可以获得通式〔IX〕和〔X〕表示的异噁唑啉化合物。应予说明,R3、R4二者为氢原子的情况下,优先获得通式〔IX〕表示的异噁唑啉化合物。
在此作为溶剂例如有乙二醇二甲醚、乙二醇二乙醚、二乙醚、二氧六环或四氢呋喃(THF)等醚,二氯乙烷、四氯化碳、氯代苯或二氯代苯等卤代烃,苯、甲苯或二甲苯等芳香烃,乙酸乙酯或乙酸丁酯等酯,水或上述的混合物等。
另外,碱如氢氧化钠、氢氧化钾等碱金属氢氧化物,氢氧化钙或氢氧化镁等碱土金属氢氧化物,碳酸钠或碳酸钾等碱金属碳酸盐,碳酸氢钠或碳酸氢钾等碱金属碳酸氢盐,醋酸钠或醋酸钾等碱金属醋酸盐,氟化钠或氟化钾等碱金属氟化物或吡啶、三乙胺或1,8-二氮杂二环〔5.4.0〕-7-十一烯等有机碱。
反应温度可以在0℃到反应体系的回流温度的任意温度下进行,优选10℃~80℃,反应因化合物而异,0.5~2小时结束。
上述制备方法中所用的制备中间体通式〔VII〕所示的化合物可以使用市售品,或者通过Wittig反应等公知反应合成。另外,通式〔VIII〕所示化合物例如可以通过《李比希化学年鉴》(Liebigs Annalen derChemie)985页(1989年)记载的方法进行合成。
<制备方法2>步骤6
式中X1、R1、R2、R3、R4、R5、R6、Y和m含义同前。R8表示C1~C4的烷基或苄基,优选表示甲基或乙基等低级烷基。Base同步骤1所示的碱。
制备方法1概述的通式〔IV〕所示的硫醚衍生物也可按以下方法获得。
即,从通式〔XI〕所示的化合物与通式〔XII〕所示的硫氢化钠水合物在适当的溶剂存在下或无溶剂存在下(优选在适当的溶剂中)、在碱(同步骤1中所记载者)的存在下(或者有时也可以添加雕白粉rongalit)反应的反应体系可以获得通式〔XIII〕所示的巯基衍生物的盐。该通式〔XIII〕所示的巯基盐无需分离与通式〔XIV〕所示的卤素衍生物反应,可以获得通式〔IV〕所示的硫醚衍生物。
在此作为溶剂例如有二氧六环、四氢呋喃(THF)等醚,二氯乙烷、四氯化碳、氯代苯或二氯代苯等卤代烃,N,N-二甲基乙酰胺、N,N-二甲基甲酰胺(DMF)或N-甲基-2-吡咯烷酮等酰胺,二甲亚砜或环丁砜等硫化合物,苯、甲苯、二甲苯等芳香烃,甲醇、乙醇、丙醇、异丙醇、丁醇或叔丁醇等醇,丙酮或2-丁酮等酮,乙腈等腈,水或上述的混合物等。
反应温度可以在0℃到反应体系的回流温度的任意温度下进行,优选10℃~100℃,反应因化合物而异,0.5~24小时结束。
另外通式〔XI〕所示的砜衍生物可以按照制备方法1中步骤1所示方法制备。此时通式〔III〕中基团-(CR5R6)m-Y表示烷基或苄基。
以下举出实施例具体说明本发明化合物的制备方法、制剂方法和用途。本发明化合物中间体的制备方法一并记载。
<实施例1>
3-苄硫基-5,5-二甲基-2-异噁唑啉(本发明化合物号1-679)的制备
氮气流下,向2.8g苄硫醇(22.5mmol)的50ml二甲基甲酰胺溶液中加入3.2g无水碳酸钾(23.2mmol)和3.0g 3-氯-5,5-二甲基-2-异噁唑啉(22.5mmol),100℃下搅拌2小时。反应终了后,将反应溶液注入水中,用乙酸乙酯萃取。有机层依次用水和食盐水洗,无水硫酸镁干燥。减压下蒸去溶剂,残渣用硅胶柱层析精制,得到3.1g 3-苄硫基-5,5-二甲基-2-异噁唑啉黄色油状物(收率62.0%),折射率nD 20=1.5521。
1H-NMR(CDCl3/TMS)δ(ppm):7.24-7.39(5H,m),4.26(2H,s),2.77(2H,s),1.40(6H,s)
<实施例2>
5-乙基-3-(2,6-二氟苄基亚磺酰基)-5-甲基-2-异噁唑啉(本发明化合物号1-199)的制备
冰冷却下,向4.1g 5-乙基-3-(2,6-二氟苄硫基)-5-甲基-2-异噁唑啉(15.0mmol)的50ml氯仿溶液中加入4.6g间氯过苯甲酸(70%)(18.8mmol),搅拌1小时,然后再在室温下搅拌12小时。反应终了后,将反应溶液注入水中,用氯仿萃取。有机相依次用亚硫酸氢钠水溶液、碳酸钾水溶液、水和食盐水洗,无水硫酸镁干燥。减压下蒸去溶剂,残渣用硅胶柱层析(溶剂系统,己烷-乙酸乙酯)精制,得到1.5g5-乙基-3-(2,6-二氟苄基亚磺酰基)-5-甲基-2-异噁唑啉白色粉末(收率34.8%)(熔点30℃以下)。
1H-NMR(CDCl3/TMS)δ(ppm):7.39-7.28(1H,m),7.03-6.94(2H,m),4.38(2H,s),3.04(2H,Abq,J=17.2,Δν=85.7Hz)+3.12(1H,s),1.75(2H,m),1.44(3H,s)+1.41(3H,s),0.97(3H,m)
<实施例3>
5-乙基-3-(2,6-二氟苄基磺酰基)-5-甲基-2-异噁唑啉(本发明化合物号1-200)的制备
冰冷却下,向0.8g 5-乙基-3-(2,6-二氟苄基亚磺酰基)-5-甲基-2-异噁唑啉(2.8mmol)的50ml氯仿溶液中加入1.0g间氯过苯甲酸(70%)(4.1mmol),搅拌1小时,然后再在室温下搅拌12小时。反应终了后,将反应溶液注入水中,用氯仿萃取。有机相依次用亚硫酸氢钠水溶液、碳酸钾水溶液、水和食盐水洗,无水硫酸镁干燥。减压下蒸去溶剂,残渣用硅胶柱层析(溶剂系统,己烷-乙酸乙酯)精制,得到0.6g 5-乙基-3-(2,6-二氟苄基磺酰基)-5-甲基-2-异噁唑啉白色粉末(收率75.0%)(熔点64~65℃)。
1H-NMR(CDCl3/TMS)δ(ppm):7.36-7.46(1H,m),6.98-7.04(2H,m),4.73(2H,s),3.04(2H,Abq,J=17.2,Δν=51.1Hz),1.77(2H,q),1.46(3H,s),0.97(3H,t)
<实施例4>
3-(2,6-二氟苄基磺酰基)-5,5-二甲基-2-异噁唑啉(本发明化合物号1-39)的制备
冰冷却下,向3.9g 3-(2,6-二氟苄硫基)-5,5-二甲基-2-异噁唑啉(15.2mmol)的50ml氯仿溶液中加入8.5g间氯过苯甲酸(70%)(34.5mmol),搅拌1小时,然后再在室温下搅拌12小时。反应终了后,将反应溶液注入水中,用氯仿萃取。有机相依次用亚硫酸氢钠水溶液、碳酸钾水溶液、水和食盐水洗,无水硫酸镁干燥。减压下蒸去溶剂,残渣用二异丙醚洗,得到3.4g 3-(2,6-二氟苄基磺酰基)-5,5-二甲基-2-异噁唑啉白色粉末(收率77.3%)(熔点110~111℃)。
1H-NMR(CDCl3/TMS)δ(ppm):7.35-7.45(1H,m),6.98-7.03(2H,m),4.72(2H,s),3.06(2H,s),1.51(6H,s)
<实施例5>
3-(2,6-二氟苄硫基)-5,5-二甲基-2-异噁唑啉(本发明化合物号1-38)的制备
冰冷却下,向5.0g 3-甲基磺酰基-5,5-二甲基-2-异噁唑啉(本发明化合物2-1)(28.2mmol)的50ml DMF溶液中加入4.5g硫氢化钠水合物(纯度70%,56.1mmol)、7.8g碳酸钾(56.4mmol)和8.7g Rongalit(56.5mmol),搅拌2小时。然后加入5.8g 2,6-二氟苄基苄基溴(28.0mmol),再在室温下搅拌12小时。反应终了后,将反应溶液注入水中,用乙酸乙酯萃取。有机相用食盐水洗,无水硫酸镁干燥。减压下蒸去溶剂,残渣用硅胶柱层析(溶剂系统,己烷-乙酸乙酯)精制,得到5.8g 3-(2,6-二氟苄硫基)-5,5-二甲基-2-异噁唑啉白色粉末(收率80.0%)(熔点77~80℃)。
1H-NMR(CDCl3/TMS)δ(ppm):7.20-7.28(1H,m),6.86-6.93(2H,m),4.35(2H,s),2.81(2H,s),1.43(6H,s)
<实施例6>
3-甲基磺酰基-5,5-二甲基-2-异噁唑啉(本发明化合物2-1)的制备
冰冷却下,向143.0g 3-氯-5,5-二甲基-2-异噁唑啉(1.07mmol)的500ml DMF溶液中滴加1.0kg甲硫醇钠的水溶液(含量15%,2.14摩尔),然后在室温下搅拌12小时。反应终了后,将反应溶液注入水中,用乙酸乙酯萃取。有机相用食盐水洗,无水硫酸镁干燥。减压下蒸去溶剂,得到115.0g 3-甲硫基-5,5-二甲基-2-异噁唑啉(收率74.1%)。该提取物(741.2mmol)溶于1L氯仿中,冰冷却下加入392.0g间氯过苯甲酸(纯度70%)(1.59摩尔),搅拌1小时,然后再在室温下搅拌12小时。反应终了后,滤去析出的间氯过苯甲酸,滤液依次用亚硫酸氢钠水溶液、水、碳酸氢钠水溶液和食盐水洗,无水硫酸镁干燥。减压下蒸去溶剂,残渣用二异丙醚洗,得到77.6g 3-甲基磺酰基-5,5-二甲基-2-异噁唑啉白色粉末(收率59.1%)(熔点82~84℃)。
1H-NMR(CDCl3/TMS)δ(ppm):3.26(3H,s),3.12(2H,s),1.516H,s)
(中间体的制备例)
<参考例1>
3-氯-5,5-二甲基-2-异噁唑啉(化合物IX)的制备
65-70℃下,向182.7g乙醛酸肟(2.05摩尔)的2L二甲氧基乙烷溶液中缓慢加入534.0g N-氯琥珀酰亚胺(4.0摩尔),然后加热回流1小时。冰冷却下加入1,440.0g碳酸氢钾(14.4摩尔)和10ml水,向反应溶液中加入360.0g 2-甲基丙烯(6.4摩尔),室温搅拌24小时。将反应溶液注入水中,用异丙基醚萃取。所得有机相依次用水和食盐水洗,用无水硫酸镁干燥。减压下蒸去溶剂,得到107.7g 3-氯-5,5-二甲基-2-异噁唑啉黄色粘稠液体(收率40.0%)。
1H-NMR(CDCl3/TMS)δ(ppm):2.93(2H,s),1.47(6H,s)
<参考例2>
3-氯-5-乙基-5-甲基-2-异噁唑啉(化合物IX)的制备
60℃下,向20.6g乙醛酸肟(231.7mmol)的500ml二甲氧基乙烷溶液中缓慢加入61.9g N-氯琥珀酰亚胺(463.4mmol)。加入结束后,加热回流10分钟。然后,在冰冷却下加入50ml 2-甲基-1-丁烯(463.4mmol)、98.9g碳酸氢钾(1622mmol)和10ml水,搅拌12小时。将反应溶液注入水中,用正己烷萃取。所得有机层依次用水和食盐水洗,用无水硫酸镁干燥。减压下蒸去溶剂,得到13.9g 3-氯-5-乙基-5-甲基-2-异噁唑啉淡黄色粘稠液体(收率40.6%)。
1H-NMR(CDCl3/TMS)δ(ppm):2.91(2H,Abq,J=17.0Δν=46.1Hz),1.73(2H,q),1.42(3H,s),0.96(3H,t)
以下所示为按照制备方法1和制备方法2所得的本发明化合物的物性值(1H-NMR(CDCl3/TMS)δ(ppm))。
本发明化合物1-6026.71-7.23(3H,m),4.84(2H,s),4.04(2H,q),2.81(2H,s),2.47(3H,s),1.43(6H,s)
本发明化合物1-6036.72-7.23(3H,m),4.85(2H,s),3.93(2H,t),2.82(2H,s),2.47(3H,s),1.83(2H,m),1.42(6H,s),1.04(3H,t)
本发明化合物1-6056.72-7.29(3H,m),4.85(2H,s),3.98(2H,t),2.81(2H,s),2.47(3H,s),1.80(2H,m),1.38(6H,s),0.97(3H,t)
本发明化合物1-6066.72-7.27(3H,m),6.05(1H,m),5.43(1H,d),5.29(1H,d),4.87(2H,s),4.57(2H,d),2.88(2H,s),2.48(3H,s),1.44(6H,s)
本发明化合物1-6076.92-7.30(3H,m),4.84(2H,s),4.74(2H,d),2.96(2H,s),2.52(1H,s),2.48(3H,s),1.46(6H,s)
本发明化合物1-2287.44-7.34(2H,m),7.02-6.92(2H,m),4.71(2H,s),3.86(3H,s),2.81(2H,Abq,J=17.4,Δν=54.2Hz),1.68(2H,q),1.36(3H,s),0.90(3H,t)
本发明化合物1-5907.28(1H,dd),7.08(1H,d),6.86(1H,d),6.05(1H,m),5.45(1H,d),5.32(1H,d),4.90(2H,s),4.63(2H,d),3.00(2H,s),1.47(6H,s)
本发明化合物1-5998.07(1H,d),7.47-7.56(3H,m),6.05(1H,m),5.42(1H,d),5.31(1H,d),5.31(2H,s),4.83(2H,d),2.94(2H,s),1.43(6H,s)
本发明的除草剂是以通式〔1〕所示的异噁唑啉衍生物或其盐为有效成分而制成的。
本发明化合物用作除草剂时,可以直接使用本发明化合物本身,也可以配合制剂中常用的载体、表面活性剂、分散剂或助剂等,以粉剂、可湿性粉剂、乳剂、微粒剂或颗粒剂等制剂使用。
制剂时使用的载体,例如滑石、膨润土、粘土、高岭土、硅藻土、白碳黑、蛭石、碳酸钙、消石灰、硅砂、硫铵、尿素等固体载体,异丙醇、二甲苯、环己烷、甲基萘等液体载体等。
表面活性剂和分散剂,例如烷基苯磺酸金属盐、二萘基甲烷二磺酸金属盐、醇硫酸酯金属盐、烷基芳基磺酸盐、木素磺酸盐、聚氧乙烯二醇醚、聚氧乙烯烷基芳基醚、聚氧乙烯脱水山梨醇单烷基醚等。助剂例如,羧甲基纤维素、聚乙二醇、阿拉伯胶等。使用时可以稀释到适当的浓度撒播或者直接施用。
本发明的除草剂可以茎叶撒播、土壤施用或者水面施用等方法使用。有效成分的配比可根据必要适当选择,粉剂或者粒剂时为0.01~10%(重量),优选0.05~5%(重量)范围内适当选择。另外,乳剂和可湿性粉剂的时候,在1~90%(重量),优选5~50%(重量)范围内选择。
本发明的除草剂的施用量因化合物的种类、对象杂草、发生倾向、环境条件以及使用的剂型等而异,如粉剂或者粒剂那样直接使用的时候,有效成分按每10公亩0.1g~5kg,优选1g~1kg范围内适当选择使用。以乳剂或者可湿性粉剂等液态使用的时候,0.1~50000ppm、优选在10~10000ppm范围内适当选择使用。
此外,本发明的化合物也可以与杀虫剂、杀菌剂、其他除草剂、植物生长调节剂、肥料等混用。
以下具体说明代表性的制剂例。化合物、添加剂的种类以及配比不限于此,可以在宽范围内变化。以下说明中,“份”表示重量份。
<制剂例1>可湿性粉剂
向10份化合物(1-5)中加入聚氧乙烯辛基苯基醚0.5份、β-萘磺酸甲醛缩合物钠盐0.5份、硅藻土20份、粘土69份混合粉碎,得到可湿性粉剂。
<制剂例2>可湿性粉剂
向10份化合物(1-5)中加入聚氧乙烯辛基苯基醚0.5份、β-萘磺酸甲醛缩合物钠盐0.5份、硅藻土20份、白碳黑5份、粘土64份混合粉碎,得到可湿性粉剂。
<制剂例3>可湿性粉剂
向10份化合物(1-5)中加入聚氧乙烯辛基苯基醚0.5份、β-萘磺酸甲醛缩合物钠盐0.5份、硅藻土20份、白碳黑5份、碳酸钙64份混合粉碎,得到可湿性粉剂。
<制剂例4>乳剂
向30份化合物(1-5)中加入二甲苯和异佛尔酮的等量混合物60份,加入10份表面活性剂聚氧乙烯脱水山梨醇烷基醚、聚氧乙烯烷基芳基醚聚合物和磺酸烷基芳基酯的混合物,充分搅拌,得到乳剂。
<制剂例5>颗粒剂
10份化合物(1-5)、80份滑石和膨润土1∶3比例混合的填充剂、5份白碳黑、5份表面活性剂聚氧乙烯脱水山梨醇烷基醚、聚氧乙烯烷基芳基醚聚合物和磺酸烷基芳基酯的混合物中加入10份水,充分捏合,成糊状,由直径0.7mm的筛孔挤出,干燥后切断成0.5~1mm的长度,得到颗粒剂。
以下举出试验例对本发明化合物的效果进行说明。
<试验例1>通过水田土壤处理的除草试验效果
100cm2的塑料制容器内填充水田土壤,耙平后,撒播稻田稗(Eo)种子,灌水深3cm。次日,将按照制剂例1制备的可湿性粉剂用水稀释,滴加到水面。施用量按每10公亩100g。然后在温室内养育,按表40基准考察处理后第21天的除草效果,如表41~表43所示。
表40
指数 | 除草效果(生长抑制程度)和药害 |
543210 | 90%以上抑制的除草效果、药害70%以上,不足90%的除草效果、药害50%以上,不足70%的除草效果、药害30%以上,不足50%的除草效果、药害10%以上,不足30%的除草效果、药害0%以上,不足10%的除草效果、药害 |
表41
化合物号 | 药量ai,g/10a | 除草效果Eo | 化合物号 | 药量ai,g/10a | 除草效果Eo |
1-11-21-31-41-51-61-71-81-321-331-341-351-381-391-401-411-421-431-461-491-551-561-581-591-1061-1391-1421-1451-1571-1581-1601-1841-1851-1861-1871-1881-1891-1901-1911-192 | 100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100 | 5555555555555555555555555555555555555555 | 1-1931-1941-1951-1981-1991-2001-2011-2021-2031-2281-2291-2301-3281-3291-3311-3361-3631-3641-3651-3661-3671-3681-3771-3781-3801-3811-3821-3831-3841-3861-3871-3881-3941-3961-3971-4011-4191-4561-457 | 100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100 | 555555555555555555555555555554555555555 |
表42
化合物号 | 药量ai,g/10a | 除草效果Eo | 化合物号 | 药量ai,g/10a | 除草效果Eo |
1-4871-4881-4891-4901-4911-4921-4931-4941-4951-4961-4971-4981-4991-5001-5011-5021-5031-5041-5051-5061-5071-5081-5091-5101-5111-5121-5131-5141-5151-5161-5171-5181-5191-5201-5211-5221-5231-5241-5251-526 | 100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100 | 5555555555555555555555555555555555555555 | 1-5271-5281-5291-5301-5311-5321-5331-5341-5351-5361-5371-5381-5391-5401-5411-5421-5431-5441-5451-5461-5471-5481-5491-5501-5511-5521-5531-5541-5551-5561-5591-5601-5611-5621-5631-5641-5651-5661-5671-568 | 100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100 | 5555555555555555555555555455555555555555 |
表43
化合物号 | 药量ai,g/10a | 除草效果Eo | 化合物号 | 药量ai,g/10a | 除草效果Eo |
1-5691-5701-5711-5721-5731-5741-5751-5761-5791-5801-5811-5831-5841-5851-5861-5881-5891-5901-5911-5931-5941-5951-5961-5971-5981-5991-6001-6011-602 | 100100100100100100100100100100100100100100100100100100100100100100100100100100100100100 | 55555555555555555555555555555 | 1-6031-6041-6051-6061-6071-6081-6091-6101-6121-6131-6141-6151-6161-6171-6181-6191-6201-6211-6221-6231-6241-6251-6261-6271-6282-22-282-29 | 100100100100100100100100100100100100100100100100100100100100100100100100100100100100 | 5555555555555555555555555555 |
<试验例2>旱田土壤处理的除草效果试验
80cm2的塑料容器内填充旱田土壤,撒播稗(Ec)、狗尾草(Se)种子,覆土。将按照制剂例1制备的可湿性粉剂用水稀释,滴加到水面。施用量按每10公亩100升的量用小型喷雾器喷洒,以达到每10公亩100g的量。然后在温室内养育,按表40基准考察处理后第21天的除草效果,如表44~表46所示。
表44
化合物号 | 药量ai,g/10a | 除草效果Ec Se | 化合物号 | 药量ai,g/10a | 除草效果Ec Se |
1-11-21-31-41-51-61-71-81-321-331-341-351-381-391-401-411-421-431-461-491-551-561-581-591-1061-1391-1421-1451-1571-1581-1601-1841-1851-1861-1871-1881-1891-1901-1911-192 | 100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100 | 5 55 55 55 55 55 55 55 55 55 55 55 54 45 55 55 55 45 55 55 55 55 55 55 55 55 55 55 55 55 55 55 45 55 55 55 55 55 55 55 5 | 1-1931-1941-1951-1981-1991-2001-2011-2021-2031-2281-2291-3281-3291-3311-3361-3631-3641-3661-3681-3781-3801-3811-3821-3831-3841-3871-3881-3941-3961-4871-4881-4891-4901-4911-4921-4931-4941-4951-4961-497 | 100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100 | 5 45 55 54 55 55 55 55 45 45 55 54 45 55 55 55 45 55 55 45 55 44 45 55 45 45 45 54 -4 55 55 45 55 45 55 55 45 55 55 45 5 |
表45
化合物号 | 药量ai,g/10a | 除草效果Ec Se | 化合物号 | 药量ai,g/10a | 除草效果Ec Se |
1-4981-4991-5001-5011-5021-5031-5041-5051-5061-5071-5081-5091-5101-5111-5121-5131-5141-5151-5161-5171-5181-5201-5211-5221-5231-5241-5251-5261-5271-5281-5291-5301-5311-5321-5341-5351-5361-5371-5381-539 | 100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100 | 5 55 55 55 55 55 55 55 55 55 55 55 55 55 55 55 55 55 55 55 55 45 55 55 55 55 55 55 55 55 55 55 55 55 45 55 55 55 55 55 5 | 1-5401-5411-5421-5431-5441-5451-5461-5471-5481-5491-5501-5511-5531-5541-5551-5561-5591-5601-5611-5621-5631-5641-5651-5661-5671-5681-5691-5701-5711-5721-5731-5741-5761-5801-5811-5831-5851-5861-5891-590 | 100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100 | 5 55 55 55 55 55 55 45 55 55 55 55 55 55 55 55 45 55 55 55 55 55 55 55 55 55 55 55 55 -5 55 55 55 55 -5 55 55 55 55 55 5 |
表46
化合物号 | 药量ai,g/10a | 除草效果Ec Se | 化合物号 | 药量ai,g/10a | 除草效果Ec Se |
1-5911-5931-5941-5951-5961-5971-5991-6001-6011-6021-6031-6041-6051-606 | 100100100100100100100100100100100100100100 | 5 55 45 45 55 55 45 55 -5 -5 55 55 55 45 5 | 1-6071-6081-6091-6101-6151-6161-6171-6181-6191-6201-6211-6222-29 | 100100100100100100100100100100100100100 | 5 55 55 55 55 55 -5 55 55 45 55 45 -5 5 |
<试验例3>通过旱田茎叶处理的除草效果试验
80cm2的塑料容器内填充旱田土壤,撒播稗(Ec)种子,覆土。温室内栽培2周后,将按照制剂例1制备的可湿性粉剂用水稀释,按每10公亩100升的施用量用小型喷雾器喷洒,以达到每10公亩100g有效成分的量。然后在温室内养育,按表40基准考察处理后第14天的除草效果,如表47、表48所示。
表47
化合物号 | 药量ai,g/10a | 除草效果Ec | 化合物号 | 药量ai,g/10a | 除草效果Ec |
1-11-21-31-41-51-61-71-81-321-351-391-401-431-461-491-551-561-581-591-1061-1391-1421-1451-1571-1581-1601-1841-1851-1861-1871-1881-1921-1931-1991-2001-2011-2021-2031-2291-336 | 100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100 | 5444544554555454555444455545554454454445 | 1-3631-3641-3661-3781-3801-3831-3971-4871-4881-4891-4901-4911-4921-4941-4951-4961-4971-4981-4991-5001-5011-5021-5031-5041-5051-5061-5071-5081-5091-5101-5111-5121-5131-5141-5151-5161-5171-5201-5211-522 | 100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100 | 4445444444444555555555455444445555555455 |
表48
化合物号 | 药量ai,g/10a | 除草效果Ec | 化合物号 | 药量ai,g/10a | 除草效果Ec |
1-5231-5241-5251-5261-5271-5281-5291-5301-5311-5321-5341-5351-5361-5371-5381-5391-5401-5411-5421-5431-5441-5451-5471-5481-5501-5531-5541-5551-5561-5591-5601-5611-562 | 100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100 | 555555555454445554445555555445444 | 1-5631-5641-5651-5661-5671-5681-5691-5701-5711-5721-5731-5741-5761-5811-5831-5841-5851-5861-5891-5901-5911-5931-5951-5991-6021-6031-6041-6061-6071-6081-6091-616 | 100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100100 | 44444555545454455544444444545555 |
<试验例4>通过水田土壤处理的作物选择性试验
100cm2的塑料制容器内填充水田土壤,耙平后,撒播稻田稗(Eo)种子,以2cm深度移植2叶水稻(0r),灌水深3cm。次日,将按照制剂例1制备的可湿性粉剂用水稀释,滴加到水面。施用量按每10公亩100g。然后在温室内养育,按表40基准考察处理后第21天的除草效果,如表49所示。
表49
化合物号 | 药量ai,g/10a | 药害除草效果Or Eo | 化合物号 | 药量ai,g/10a | 药害 除草效果Or Eo |
1-1451-1901-1981-2031-2281-2291-2301-3281-3311-3651-3671-3681-3771-3841-3861-3941-4011-4191-4561-4571-5031-5181-5191-5201-5491-5521-556 | 100100100100100100100100100100100100100100100100100100100100100100100100100100100 | 0 51 51 51 51 51 50 50 50 51 51 51 50 50 50 41 50 51 50 51 50 51 50 51 51 51 40 5 | 1-5741-5791-5801-5841-5881-5901-5941-5961-5971-5981-5991-6011-6051-6101-6121-6131-6141-6151-6201-6221-6231-6241-6251-6261-6271-6282-22-29 | 100100100100100100100100100100100100100100100100100100100100100100100100100100100100 | 1 51 51 51 51 51 51 51 51 51 51 51 51 51 50 50 50 51 51 51 51 51 51 50 51 50 50 51 5 |
<试验例5>通过水田土壤处理的生长期除草效果试验
100cm2的塑料制容器内填充水田土壤,耙平后,撒播鸭舌草(Mo)、萤蔺Scirpus juncoides Roxb.subsp.juncoides Roxb.(Sc)种子,灌水深3cm,培育杂草。鸭舌草生长至1叶、萤蔺生长至2叶时,将按照制剂例1制备的可湿性粉剂用水稀释,滴加到水面。施用量以有效成分每10公亩100g。然后在温室内养育,按表40基准考察处理后第30天的除草效果,如表51所示。对照化合物1和2如表50所示。
表50
表51
化合物号 | 药量ai,g/10a | 除草效果Mo Sc | |
1-81-391-491-581-1571-3821-5471-567比较1比较2 | 25252525252525252525 | 5554555511 | 4555545511 |
<试验例6>对旱田土壤处理对阔叶杂草除草效果的效果
80cm2的塑料容器内填充旱田土壤,撒播马蓼Polygonumlapathifolium L.subsp.nodosum(pers.)kitam.(Po)、藜(Ch)种子,覆土。将按照制剂例1制备的可湿性粉剂用水稀释,按每10公亩100升的施用量用小型喷雾器均匀喷洒到土壤表面,以达到每10公亩100g的量。然后在温室内养育,按表40基准考察处理后第30天的除草效果,结果如表52所示。对照化合物1和3如表50所示。
表52
化合物号 | 药量ai,g/10a | 除草效果Po Ch |
1-21-391-461-4981-4991-5001-5011-5231-5261-5321-5341-5551-573比较1比较3 | 252525252525252525252525252525 | - 44 55 45 55 45 45 55 55 55 55 55 45 50 01 0 |
工业实用性
通式(1)所示本发明化合物可以在从发芽前期直到生育期的长时间范围内以低剂量对各种旱田杂草发挥优良的除草效果,所述杂草例如稗、马唐、狗尾草、早熟禾、阿拉伯高粱、看麦娘、野燕麦等禾本科杂草,马蓼、绿苋、藜、苘麻、美洲黄花稔(Sida spinosa)、决明(Cassiaobtusifolia)、美洲豚草、牵牛等阔叶杂草,莎草、油莎草、水蜈蚣、具芒碎米莎草、碎米莎草等多年生和1年生莎草科杂草。
另外,本发明化合物可以在从发芽前期直到生育期的长时间范围内以低剂量对水田杂草如稻田稗、异型莎草、陌上菜等1年生杂草,水莎草、鸟芋荸荠(Eleocharis kuroguwai)、萤蔺(Scirpus juncoides Roxb.subsp.hotarui)等多年生杂草发挥防治作用。
另一方面,本发明的除草剂对作物的安全性高,其中特别对稻、小麦、大麦、玉米、高粱、大豆、棉花、甜菜、结缕草、果树等显示高的安全性。
Claims (4)
式中,Q表示基团-S(O)n-(CR5R6)m-,n表示0~2的整数,m表示1~3的整数,R5和R6彼此独立表示氢原子、氰基、烷氧羰基或C1~C6烷基;
R1和R2表示氢原子、〔可以被C3~C8环烷基、C1~C6烷氧基、C1~C6烷基羰基、C1~C6烷硫基、C1~C6烷基亚磺酰基、C1~C6烷基磺酰基、C1~C6烷氨基、二(C1~C6烷基)氨基、羟基、氰基、C1~C6烷氧羰基、C1~C6烷基氨基羰基、二(C1~C6烷基)氨基羰基、(C1~C6烷硫基)羰基、羧基、(可以被取代的)苄氧基、(可以被取代的)苯氧基或(可以被取代的)苯基取代的〕C1~C8烷基、C3~C8环烷基、C1~C6烷氧羰基、C1~C6烷基氨基羰基、二(C1~C6烷基)氨基羰基、或(C1~C6烷硫基羰基、羧基或可以被取代的)苯基,或者R1和R2也可以与结合了上述基团的碳原子共同形成C3~C7的螺环;
R3和R4表示氢原子、(可以被相同或不同的1~3个卤素原子、C3~C8环烷基或C1~C6烷氧基取代的)C1~C8烷基或C3~C8环烷基,R3和R4也可以与结合了上述基团的碳原子共同形成C3~C7的螺环,或者R1、R2、R3和R4也可以与结合了上述基团的碳原子共同形成5~8员环;
Y表示氢原子、C1~C6烷氧羰基、羧基、C2~C6链烯基、〔可以被相同或不同的1~3个卤素原子、C1~C6烷氧基、C2~C6烯氧基、C2~C6炔氧基、(可以被取代的)苄氧基、C1~C6烷氧羰基、羧基、羟基或甲酰基取代的〕C1~C10烷基或(被1~5个相同或不同的R7取代的)苯基;
R7表示氢原子、〔可以被相同或不同的1~3个卤素原子、C1~C6烷氧基、羟基、C1~C6烷硫基、C1~C6烷硫基、C1~C6烷基亚磺酰基、C1~C6烷基磺酰基、C1~C6烷基氨基、二(C1~C6)烷基氨基、氰基或(可以被取代的)苯氧基取代的〕C1~C6烷基、(可以被相同或不同的1~3个卤素原子、C1~C6烷氧基、C2~C6链烯基、C2~C6炔基、C1~C6烷氧羰基、C1~C6烷基羰基或C3~C8环烷基取代的)C1~C6烷氧基、C2~C6链烯基、C3~C8环烷氧基、(可以被相同或不同的1~3个卤素原子或C1~C6烷氧基取代的)C1~C6烷硫基、(可以被相同或不同的1~3个卤素原子或C1~C6烷氧基取代的)C1~C6烷基亚磺酰基、(可以被相同或不同的1~3个卤素原子或C1~C6烷氧基取代的)C1~C6烷基磺酰基、(可以被取代的)苄氧基、(可以被C1~C6烷基、C1~C6烷基磺酰基、C1~C6烷基羰基(C1~C6烷基)或C1~C6烷基磺酰基(C1~C6烷基)取代的)氨基、二(C1~C6烷基)氨基、卤素原子、氰基、硝基、C1~C6烷氧羰基、C3~C8环烷氧羰基、羧基、C2~C6烯氧羰基、C2~C6炔氧羰基、(可以被取代的)苄氧羰基、(可以被取代的)苯氧羰基或者C1~C6烷基羰氧基。
2.权利要求1所示的异噁唑啉衍生物及其盐,其中通式〔1〕中,
Q表示基团-S(O)n-(CR5R6)m-,n表示0~2的整数,m表示1,R5和R6表示氢原子;
R1和R2表示氢原子、(可以被C3~C8环烷基或C1~C6烷氧基取代的)C1~C8烷基或C3~C8环烷基,或者R1和R2也可以与结合了上述基团的碳原子共同形成C3~C7的螺环;
R3和R4表示氢原子或(可以被相同或不同的1~3个卤素原子、C3~C8环烷基或C1~C6烷氧基取代的)C1~C8烷基,R3和R4也可以与结合了上述基团的碳原子共同形成C3~C7的螺环,或者R1、R2、R3和R4也可以与结合了上述基团的碳原子共同形成5~8员环;
Y表示(被1~5个相同或不同的R7取代的)苯基;
R7表示氢原子、〔可以被相同或不同的1~3个卤素原子、C1~C6烷氧基、羟基、C1~C6烷硫基、C1~C6烷基亚磺酰基、C1~C6烷基磺酰基、C1~C6烷基氨基、C1~C6二烷基氨基、氰基或(可以被取代的)苯氧基取代的〕C1~C6烷基、(可以被相同或不同的1~3个卤素原子、C1~C6烷氧基、C2~C6链烯基、C2~C6炔基、C1~C6烷氧羰基、C1~C6烷基羰基或C3~C8环烷基取代的)C1~C6烷氧基、C3~C8环烷氧基或卤素原子。
3.权利要求1所示的异噁唑啉衍生物及其盐,其中通式〔1〕中,
Q表示基团-S(O)n-(CR5R6)m-,n表示0~2的整数,m表示1,R5和R6表示氢原子;
R1和R2表示C1~C8烷基;
R3和R4表示氢原子;
Y表示(被1~5个相同或不同的R7取代的)苯基;
R7表示氢原子、(可以被相同或不同的1~3个卤素原子或C1~C6烷氧基取代的)C1~C6烷基、(可以被相同或不同的1~3个卤素原子或C1~C6烷氧基取代的)C1~C6烷氧基或卤素原子。
4.含有权利要求1~3中任一项记载的异噁唑啉衍生物或其盐作为有效成分的除草剂。
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CN113929637B (zh) * | 2021-11-17 | 2024-02-06 | 山东大学 | 一种含硫基二氢异恶唑类化合物及其合成方法 |
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CZ2002461A3 (cs) | 2002-05-15 |
ATE318801T1 (de) | 2006-03-15 |
JP4299483B2 (ja) | 2009-07-22 |
ZA200200392B (en) | 2003-03-26 |
CZ301045B6 (cs) | 2009-10-21 |
KR20020027537A (ko) | 2002-04-13 |
CN1170825C (zh) | 2004-10-13 |
DE60026318D1 (de) | 2006-04-27 |
AU769834B2 (en) | 2004-02-05 |
AU6472500A (en) | 2001-03-13 |
RU2237664C2 (ru) | 2004-10-10 |
UA73520C2 (uk) | 2005-08-15 |
EP1203768A4 (en) | 2002-10-16 |
EP1203768A1 (en) | 2002-05-08 |
WO2001012613A1 (fr) | 2001-02-22 |
CA2380499C (en) | 2011-01-04 |
US6841519B1 (en) | 2005-01-11 |
BR0013251B1 (pt) | 2010-11-30 |
KR100602776B1 (ko) | 2006-07-20 |
HU230517B1 (hu) | 2016-10-28 |
BR0013251A (pt) | 2002-04-16 |
EP1203768B1 (en) | 2006-03-01 |
HUP0202799A3 (en) | 2005-05-30 |
CA2380499A1 (en) | 2001-02-22 |
DE60026318T2 (de) | 2006-08-10 |
IL147651A (en) | 2008-11-26 |
HUP0202799A2 (hu) | 2003-01-28 |
IL147651A0 (en) | 2002-08-14 |
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