CN1149211C - 苯甲酰衍生物,其制法及其作为除草剂和植物生长调节剂的用途 - Google Patents
苯甲酰衍生物,其制法及其作为除草剂和植物生长调节剂的用途 Download PDFInfo
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- CN1149211C CN1149211C CNB998105945A CN99810594A CN1149211C CN 1149211 C CN1149211 C CN 1149211C CN B998105945 A CNB998105945 A CN B998105945A CN 99810594 A CN99810594 A CN 99810594A CN 1149211 C CN1149211 C CN 1149211C
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- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 title claims abstract description 21
- 239000005648 plant growth regulator Substances 0.000 title abstract description 5
- 239000004009 herbicide Substances 0.000 title abstract description 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 40
- -1 methoxyl group Chemical group 0.000 claims description 298
- 150000001875 compounds Chemical class 0.000 claims description 132
- 229910052760 oxygen Inorganic materials 0.000 claims description 96
- 239000001301 oxygen Substances 0.000 claims description 90
- 229910052736 halogen Inorganic materials 0.000 claims description 89
- 229910052739 hydrogen Inorganic materials 0.000 claims description 74
- 239000000203 mixture Substances 0.000 claims description 62
- 239000001257 hydrogen Substances 0.000 claims description 57
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 54
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 53
- 125000000217 alkyl group Chemical group 0.000 claims description 49
- 150000002367 halogens Chemical class 0.000 claims description 48
- 125000001072 heteroaryl group Chemical group 0.000 claims description 45
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 42
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
- 239000005864 Sulphur Chemical group 0.000 claims description 25
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 22
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 150000001721 carbon Chemical group 0.000 claims description 17
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 14
- 238000009472 formulation Methods 0.000 claims description 13
- 230000012010 growth Effects 0.000 claims description 12
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
- 244000038559 crop plants Species 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 230000002363 herbicidal effect Effects 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 21
- 238000002360 preparation method Methods 0.000 abstract description 15
- OILAIQUEIWYQPH-UHFFFAOYSA-N cyclohexane-1,2-dione Chemical group O=C1CCCCC1=O OILAIQUEIWYQPH-UHFFFAOYSA-N 0.000 abstract description 3
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical group C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 abstract description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical group C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 description 569
- 239000002585 base Substances 0.000 description 271
- 241000196324 Embryophyta Species 0.000 description 69
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 49
- 125000003545 alkoxy group Chemical group 0.000 description 43
- 125000003118 aryl group Chemical group 0.000 description 43
- 238000006243 chemical reaction Methods 0.000 description 39
- 125000000753 cycloalkyl group Chemical group 0.000 description 36
- 239000003795 chemical substances by application Substances 0.000 description 33
- 238000005160 1H NMR spectroscopy Methods 0.000 description 31
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 28
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 28
- 239000000178 monomer Substances 0.000 description 26
- 125000004076 pyridyl group Chemical group 0.000 description 26
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 26
- 229920002554 vinyl polymer Polymers 0.000 description 26
- 239000013543 active substance Substances 0.000 description 25
- 125000000304 alkynyl group Chemical group 0.000 description 25
- 125000002769 thiazolinyl group Chemical group 0.000 description 25
- 230000000694 effects Effects 0.000 description 24
- 239000000126 substance Substances 0.000 description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 23
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 21
- 150000002148 esters Chemical class 0.000 description 20
- 150000003216 pyrazines Chemical class 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 239000000741 silica gel Substances 0.000 description 18
- 229910002027 silica gel Inorganic materials 0.000 description 18
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 17
- 125000002521 alkyl halide group Chemical group 0.000 description 17
- 150000002431 hydrogen Chemical class 0.000 description 17
- 244000025254 Cannabis sativa Species 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 125000004414 alkyl thio group Chemical group 0.000 description 15
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 15
- 238000002156 mixing Methods 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 239000002253 acid Substances 0.000 description 14
- 239000013078 crystal Substances 0.000 description 14
- 239000005077 polysulfide Substances 0.000 description 14
- 229920001021 polysulfide Polymers 0.000 description 14
- 150000008117 polysulfides Polymers 0.000 description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 14
- 150000001345 alkine derivatives Chemical class 0.000 description 13
- 125000000623 heterocyclic group Chemical group 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- 229920006395 saturated elastomer Polymers 0.000 description 13
- 150000001336 alkenes Chemical class 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 125000005842 heteroatom Chemical group 0.000 description 11
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 description 11
- 239000002245 particle Substances 0.000 description 11
- 108090000623 proteins and genes Proteins 0.000 description 11
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 description 10
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 10
- 125000005133 alkynyloxy group Chemical group 0.000 description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 10
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- 239000004563 wettable powder Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- 239000012141 concentrate Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 8
- 125000005108 alkenylthio group Chemical group 0.000 description 8
- 125000003282 alkyl amino group Chemical group 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 125000005357 cycloalkylalkynyl group Chemical group 0.000 description 8
- 125000005312 heteroarylalkynyl group Chemical group 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 8
- 239000002689 soil Substances 0.000 description 8
- 238000009333 weeding Methods 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 7
- 240000007594 Oryza sativa Species 0.000 description 7
- 235000007164 Oryza sativa Nutrition 0.000 description 7
- 125000005018 aryl alkenyl group Chemical group 0.000 description 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 7
- 235000009566 rice Nutrition 0.000 description 7
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 description 6
- 125000005129 aryl carbonyl group Chemical group 0.000 description 6
- 238000006555 catalytic reaction Methods 0.000 description 6
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 6
- 230000006378 damage Effects 0.000 description 6
- 244000037671 genetically modified crops Species 0.000 description 6
- 230000002650 habitual effect Effects 0.000 description 6
- 125000000262 haloalkenyl group Chemical group 0.000 description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 description 6
- 239000000575 pesticide Substances 0.000 description 6
- 230000008635 plant growth Effects 0.000 description 6
- BACHBFVBHLGWSL-JTQLQIEISA-N rac-diclofop methyl Natural products C1=CC(O[C@@H](C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-JTQLQIEISA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
- 235000007340 Hordeum vulgare Nutrition 0.000 description 5
- 240000005979 Hordeum vulgare Species 0.000 description 5
- 229910004298 SiO 2 Inorganic materials 0.000 description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 5
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000010410 dusting Methods 0.000 description 5
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- 150000004702 methyl esters Chemical class 0.000 description 5
- 235000019260 propionic acid Nutrition 0.000 description 5
- 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 5
- 239000007921 spray Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 5
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- 235000007319 Avena orientalis Nutrition 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical group CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 4
- RMFGNMMNUZWCRZ-UHFFFAOYSA-N Humulone Natural products CC(C)CC(=O)C1=C(O)C(O)(CC=C(C)C)C(O)=C(CC=C(C)C)C1=O RMFGNMMNUZWCRZ-UHFFFAOYSA-N 0.000 description 4
- SENJXOPIZNYLHU-IUCAKERBSA-N Leu-Arg Chemical compound CC(C)C[C@H](N)C(=O)N[C@H](C(O)=O)CCCN=C(N)N SENJXOPIZNYLHU-IUCAKERBSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
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- 125000004171 alkoxy aryl group Chemical group 0.000 description 4
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- 239000007762 w/o emulsion Substances 0.000 description 1
- 239000004552 water soluble powder Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 description 1
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- C07D335/10—Dibenzothiopyrans; Hydrogenated dibenzothiopyrans
- C07D335/12—Thioxanthenes
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Abstract
本发明涉及式(I)的苯甲酰衍生物,其制法及其作为除草剂和植物生长调节剂的用途。在该式(I)中,R1、R2、R3、R4及R5为不同的有机基团,Q为异噻唑、异噁唑、环己二酮或β-酮腈残基且A、B、E及X为含一或多个原子的二价单元。
Description
本发明系关于除草剂和植物生长调节剂的技术领域,尤其是在有用植物的栽培中供选择性地控制阔叶杂草及杂草的除草剂。
从许多刊物已知部分苯甲酰衍生物具有除草剂性质,EP-A 0 712 853及EP-A 0 841 335揭示稠合的苯甲酰衍生物,其在稠合环体系的α位置上带有一个烷基。
EP-A 0 629 623、EP-A 0 810 227及EP-A 0 819 691揭示稠合的苯甲酰衍生物,其在稠合环体系的α位置经一个烷氧基取代,WO97/23135揭示稠合的苯甲酰衍生物,其在稠合环体系的α位置上带有一个选自烷基、烯基、炔基、烷氧基及烷氧亚氨基的基团,WO 98/29406揭示稠合的苯甲酰衍生物,其在稠合环体系的α位置上带有一或两个选自烷基、烷氧亚氨基、烷氧基、烷硫基及二取代氨基的基团,在此,最后提到的三种基团也可以环状形式存在,所以环烷氧基、环烷硫基或环烷氨基可存在于稠合环体系的α位置,此外,WO 98/29406提到一种稠合的苯甲酰衍生物,其中一个(2-四氢呋喃基)甲氧基存在于上述的α位置。
而且,从不同的刊物已知苯甲酰环己二酮类作为对羟基苯基丙酮酸双加氧酶抑制剂的除草剂是建立在与苯甲酰异噁唑类相同的活性机制上,见农药科学杂志(J.Pesticide Sci.)21,473-478(1996),杂草科学(Weed Science)45,601-609(1997),农药科学(Pesticide Science)50,83-84,(1997)及Pesticide Outlook,29-32,(December 1996),此外,从Pesticide Science 50,83-84,(1997)已知式(A)的苯甲酰异噁唑在某些情形下可重排而得到式(B)的苯甲酰基-3-氧代丙腈。
但是,实施从这些刊物已知的苯甲酰衍生物的用途时常伴随着缺点,例如,已知化合物的除草或植物生长调节活性并非都足够,或当除草活性足够时,发现会不希望地伤害有用的植物。
本发明的目的是提供可克服现有技术已知缺点的除草剂和植物生长调节性化合物。
此目的经由式(I)的苯甲酰衍生物而实现,
其中
Q为式(II)、(III)或(IV)的基
R1、R2、R3彼此独立地为氢、羟基、硫基、氨基、氰基、硝基、卤素或未经取代或经取代的烃基,其还可含或不含一或多个选自氧、硫、氮、氟、氯、溴及碘的相同或不同的杂原子;
R4为氢、氰基、烷基、烯基、炔基、环烷基、烷氧羰基、苯基,其中六种最后提到的基团为未经取代或经一或多个选自卤素、硝基、氰基、烷基、环烷基、烯基、炔基、烷氧基及烷硫基的相同或不同的基团取代;
R5为杂芳基、杂环基或芳基,它们为未经取代或经相同或不同的基团单-或多取代,或为选自-O-N=CRlRm、-P(=O)(ORi)(Rj)、-P(=O)(ORi)(ORk)或下式的基团
或如果E为一个键且l为0时,R5也可为羟基,A为选自O、S、SO、SO2、NRa、CHRa、CRaRb的二价单元;
B为含一至四个碳原子的链,其为饱和或含一或多个重键且其为未经取代或经烷基、卤烷基、烷氧基、卤烷氧基或未经取代或经烷基-、卤烷基-、烷氧基-、卤烷氧基-、卤素-、氰基-或硝基-取代的苯基取代;
E为一个键、一-至六-元链,其为饱和或含一或多个重键且其由选自C、CRc、CRcRd、N、NRc、S、SO、SO2、O及CO的二价单元构成;
X为选自O、S及NRe的二价单元;
R6为烷硫基、卤烷硫基、烷亚磺酰基、卤烷亚磺酰基、烷磺酰基、卤烷磺酰基、氰基、氰氧基、氰硫基、卤素或ORf;
Y为选自O、S、NH、N-烷基或CHR7的二价单元;
R7为氢、四氢吡喃-3-基、四氢吡喃-4-基、四氢噻喃-3-基、烷基、环烷基、烷氧基、烷氧基烷基、烷基羰基、烷氧羰基、烷硫基、苯基,其中八种最后提到的基团的烃基部分为未经取代或经一或多个选自卤素、烷硫基及烷氧基的相同或不同的基团取代;或
连结至共同碳原子的两个R7基形成选自OCH2CH2O、OCH2CH2CH2O、SCH2CH2S及SCH2CH2CH2S的链,此链为未经取代或经一至四个甲基取代;
或
连结至直接相邻的碳原子的两个R7基形成一个键或与携带它们的碳原子形成未经取代或经取代的3-至6-元环;
Z为一个键、选自O、S、SO、SO2、NH、N-烷基或CHR7的二价单元,其中Y及Z不能同时为含氧、氮或硫原子作为链单元的二价单元;
G1-G2为选自OCR9、SCR9及NR10COR11的二价单元,其中进行连接至环体系以使此二价单元的碳原子在各情形下是经由双键连接至环体系的碳原子;
R8为氢、烷基或烷氧羰基;
R9为氢、烷基、环烷基、卤烷基或卤环烷基;
R10为氢、烷基、烯基、炔基、环烷基、苯基、苄基,其中六种最后提到的基团为未经取代或经一或多个选自卤素、氰基、硝基及烷氧基的相同或不同的的基团取代;
R11为氢、甲酰基、烷基、卤烷基、烷氧基烷基或L-R12基;
L为选自SO2、CO、CHRgCO或CRgRh的二价单元;
R12为烷基、卤烷基、烷氧基、卤烷氧基、烷氨基、二烷氨基、环烷基或为苯基,其为未经取代或经一或多个选自氰基、硝基、烷基、烷氧基、卤烷基及卤烷氧基的相同或不同的的基团取代;
Ra及Rb彼此独立地为氢、卤素、氰基、硝基、甲酰基、烷基、环烷基、烯基、炔基、烷基羰基及烷基磺酰基,其中六种最后提到的基团的烃基部分为未经取代或经一或多个选自卤素、硝基、氰基、烷基、环烷基、烯基、炔基、烷氧基及烷硫基的相同或不同的基团取代;
Rc及Rd彼此独立地为氢、卤素、硝基、氰基、烷基、卤烷基、环烷基、烯基、卤烯基、炔基、卤炔基、烷氧基、卤烷氧基、烷硫基、卤烷硫基、烷基羰基、卤烷基羰基、烷氧羰基、卤烷氧羰基、氨基羰基、烷氨基羰基、二烷氨基羰基、卤烷基羰基氨基、烷基羰基-N-烷氨基、烷基磺酰基、烷基亚磺酰基、烷基磺酰基氨基、卤烷基磺酰基、卤烷基亚磺酰基、烷基磺酰基氨基及烷基磺酰基-N-烷氨基;
Re为氢、甲酰基、烷基、环烷基、烯基、炔基、烷基羰基及烷基磺酰基,其中六种最后提到的基团的烃基部分为未经取代或经一或多个选自卤素、硝基、氰基、烷基、环烷基、烯基、炔基、烷氧基及烷硫基的相同或不同的基团取代;
Rf为氢、烷基、卤烷基、烷氧基烷基、甲酰基、烷基羰基、烷氧羰基、烷氨基羰基、二烷氨基羰基、烷基磺酰基、卤烷基磺酰基、苯甲酰基或苯基磺酰基,其中两种最后提到的基团的芳族部分为未经取代或经一或多个选自烷基、卤烷基、烷氧基、卤烷氧基、卤素、氰基及硝基的相同或不同的基团取代;
Rg及Rh彼此独立地为氢或烷基;
Ri及Rk彼此独立地为氢或Rj;
Rj为烷基、烯基、卤烷基、卤烯基、苯基、苄基,其中这六种上述基团为未经取代或经一或多个选自卤素、氰基、硝基、(C1-C4)-烷基、(C1-C4)-烷氧基、卤代-(C1-C4)-烷基或卤代-(C1-C4)-烷氧基的相同或不同的基团取代;
Rl及Rm彼此独立地为氢或烷基、烯基、炔基、卤烷基、卤烯基或卤炔基,它们经一或多个相同或不同的Rl基团取代;或
Rl及Rm与和其连接的碳原子形成3-、4-、5-、6-、7-或8-元饱和或部分不饱和的环,其可含或不含一至三个选自氧、硫及氮的杂原子且其为未经取代或经一或多个相同或不同的Rl基团取代;
l为0或1;
m为0、1或2;
n为0、1、2或3;
v为1或2;
w为0、1、2、3或4;
其条件是
a)上述定义不包括化合物4-[2-四氢呋喃基]甲氧基-5,8-二甲基-6-[(2,6-二氧代环己基)羰基]-1,2,3,4-四氢-1λ6-硫色烯-1,1-二酮,且
b)如果E为亚甲基,且在G1-G2中的G1为硫,在R5中,芳基不是苯基。
决定于外部情形,例如溶剂及pH,大量根据本发明的式(I)化合物可存在不同的互变异构性结构。
在Q为其中R6为羟基的式(II)基的情形下,可能有下列的互变异构性结构:
在Q为式(IV)基的情形下,可能有下列的互变异构性结构:
这些互变异构性结构也包括在式(I)内。
决定于取代基的类型,式(I)化合物含的酸性质子可经由与碱反应去除,合适的碱为例如碱金属例如锂、钠及钾、碱土金属例如钙及镁、氨及有机胺类,此种盐类也形成本发明主题的一部分。
烃基为直链,支链或环状且饱和、部分饱和、不饱和或芳族基,例如烷基、烯基、炔基、环烷基、环烯基、环炔基或芳基,此定义也包括组合名称,例如环烷基烯基、环炔基烷基及芳基炔基,如果此烃基另外含杂原子,这些杂原子可原则上位于,也就是化学结构容许的烃基的任何位置。
在式(I)及全部后续的化学式中,链形式的含碳基的基,例如烷基、烷氧基、卤烷基、卤烷氧基、烷氨基及烷硫基,及碳链中相对应的不饱和及/或经取代的基,例如烯基及炔基,在各情形下可为直链或支链,除非特别说明,在这些基团中优选为低碳数结构,例如含1至6个碳原子,或在不饱和基的情形下,含2至4个碳原子,烷基,即使在组合定义例如烷氧基、卤烷基等中为例如甲基、乙基、正-或异丙基、正-、异-、叔-或仲丁基、戊基、己基例如正己基、异己基及1,3-二甲丁基、庚基例如正庚基、1-甲基己基及1,4-二甲基戊基;烯基及炔基具有相对应于烷基且可能的不饱和基的定义,烯基为例如烯丙基、1-甲基丙-2-烯-1-基、2-甲基丙-2-烯-1-基、丁-2-烯-1-基、丁-3-烯-1-基、1-甲基-丁-3-烯-1-基及1-甲基-丁-2-烯-1-基;炔基为例如炔丙基、丁-2-炔-1-基、丁-3-炔-1-基、1-甲基丁-3-炔-1-基,重键可位于不饱和基的任何位置。
环烷基为含三至八个碳原子的碳环饱和环体系,例如环丙基、环戊基或环己基,同样地,环烯基为含三至八个碳环原子的单环烯基,例如环丙烯基、环丁烯基、环戊烯基及环己烯基,其中双键可位于任何位置,在组合基团的情形下,例如环烷基烯基,第一次提到的基团可位于第二次提到的基团的任何位置。
在双取代的氨基情形下,例如二烷氨基,这两个基可相同或不同。
卤素为氟、氯、溴或碘,卤烷基、-烯基及-炔基分别为部分或完全经卤素取代的烷基、烯基或炔基,优选经氟、氯及/或溴取代,尤其是经氟或氯取代,例如CF3、CHF2、CH2F、CF3CF2、CH2FCHCl、CCl3、CHCl2、CH2CH2Cl;卤烷氧基为例如OCF3、OCHF2、OCH2F、CF3CF2O、OCH2CF3及OCH2CH2Cl;此相对应地适用于卤烯基及其他经卤素取代的基。
所称的杂环基是指三-至六-元饱和或部分不饱和的单-或多环杂环,其中含一至三个选自氧、氮及硫的杂原子,连接可出现在杂环的化学上可能的任何位置,实例为环氧乙烷基、3-四氢呋喃基、2-四氢噻吩基、3-四氢噻吩基、1-吡咯烷基、2-吡咯烷基、3-吡咯烷基、3-异噁唑烷基、4-异噁唑烷基、5-异噁唑烷基、3-异噻唑烷基、4-异噻唑烷基、5-异噻唑烷基、1-吡唑烷基、3-吡唑烷基、4-吡唑烷基、5-吡唑烷基、2-噁唑烷基、4-噁唑烷基、5-噁唑烷基、2-噻唑烷基、4-噻唑烷基、5-噻唑烷基、2-咪唑烷基、4-咪唑烷基、1,2,4-噁二唑烷-3-基、1,2,4-噁二唑烷-5-基、1,2,4-噻二唑烷-3-基、1,2,4-噻二唑烷-5-基、1,2,4-三唑烷-3-基、1,3,4-噁唑烷-2-基、1,3,4-噻二唑烷-2-基、1,3,4-三唑烷-2-基、2,3-二氢呋喃-2-基、2,3-二氢呋喃-3-基、2,3-二氢呋喃-4-基、2,3-二氢呋喃-5-基、2,5-二氢呋喃-2-基、2,5-二氢呋喃-3-基、2,3-二氢噻吩-2-基、2,3-二氢噻吩-3-基、2,3-二氢噻吩-4-基、2,3-二氢噻吩-5-基、2,5-二氢噻吩-2-基、2,5-二氢噻吩-3-基、2,3-二氢吡咯-2-基、2,3-二氢吡咯-3-基、2,3-二氢吡咯-4-基、2,3-二氢吡咯-5-基、2,5-二氢吡咯-2-基、2,5-二氢吡咯-3-基、2,3-二氢异噁唑-3-基、2,3-二氢异噁唑-4-基、2,3-二氢异噁唑-5-基、4,5-二氢异噁唑-3-基、4,5-二氢异噁唑-4-基、4,5-二氢异噁唑-5-基、2,5-二氢异噻唑-3-基、2,5-二氢异噻唑-4-基、2,5-二氢异噻唑-5-基、2,3-二氢异吡唑-3-基、2,3-二氢异吡唑-4-基、2,3-二氢异吡唑-5-基、4,5-二氢异吡唑-3-基、4,5-二氢异吡唑-4-基、4,5-二氢异吡唑-5-基、2,5-二氢异吡唑-3-基、2,5-二氢异吡唑-4-基、2,5-二氢异吡唑-5-基、2,3-二氢噁唑-3-基、2,3-二氢噁唑-4-基、2,3-二氢噁唑-5-基、4,5-二氢噁唑-3-基、4,5-二氢噁唑-4-基、4,5-二氢噁唑-5-基、2,5-二氢噁唑-3-基、2,5-二氢噁唑-4-基、2,5-二氢噁唑-5-基、2,3-二氢噻唑-2-基、2,3-二氢噻唑-4-基、2,3-二氢噻唑-5-基、4,5-二氢噻唑-2-基、4,5-二氢噻唑-4-基、4,5-二氢噻唑-5-基、2,5-二氢噻唑-2-基、2,5-二氢噻唑-4-基、2,5-二氢噻唑-5-基、2,3-二氢咪唑-2-基、2,3-二氢咪唑-4-基、2,3-二氢咪唑-5-基、4,5-二氢咪唑-2-基、4,5-二氢咪唑-4-基、4,5-二氢咪唑-5-基、2,5-二氢咪唑-2-基、2,5-二氢咪唑-4-基、2,5-二氢咪唑-5-基、1-吗啉基、2-吗啉基、3-吗啉基、1-哌啶基、2-哌啶基、3-哌啶基、4-哌啶基、3-四氢哒嗪基、4-四氢塔嗪基、2-四氢嘧啶基、4-四氢嘧啶基、5-四氢嘧啶基、2-四氢吡嗪基、1,3,5-四氢三嗪-2-基、1,2,4-四氢三嗪-3-基、1,3-二氢噁嗪-2-基、1,3-二噻烷-2-基、2-四氢吡喃基、1,3-二氧戊环-2-基、3,4,5,6-四氢吡啶-2-基、4H-1,3-噻嗪-2-基、4H-3,1-苯并噻嗪-2-基、1,3-二噻烷-2-基、1,1-二氧代-2,3,4,5-四氢噻吩-2-基、2H-1,4-苯并噻嗪-3-基、2H-1,4-苯并噁嗪-3-基、1,3-二氢噁嗪-2-基。
芳基为芳族单-或多环烃基,例如苯基、萘基、联苯基及菲基,连接可出现在化学上可能的芳基上的任何位置。
杂芳基为芳族单-、二-或三环基团,其除了碳环原子以外,还含一至四个氮原子或一至三个氮原子及一个氧或一个硫原子或一个氧或一个硫原子,连接可出现在化学上可能的芳基上的任何位置,5-元杂芳基实例为2-吡咯基、3-吡咯基、1-吡唑基、3-吡唑基、4-吡唑基、5-吡唑基、2-咪唑基、4-咪唑基、1,2,4-三唑-3-基、1,3,4-三唑-2-基、2-呋喃基、3-呋喃基、2-噻吩基、3-噻吩基、2-吡咯基、3-吡咯基、3-异噁唑基、4-异噁唑基、5-异噁唑基、3-异噻唑基、4-异噻唑基、5-异噻唑基、3-吡唑基、4-吡唑基、5-吡唑基、2-噁唑基、4-噁唑基、5-噁唑基、2-噻唑基、4-噻唑基、5-噻唑基、2-咪唑基、1,2,4-噁二唑-3-基、1,2,4-噁二唑-5-基、1,2,4-噻二唑-3-基、1,2,4-噻二唑-5-基、1,2,4-三唑-3-基、1,3,4-噁二唑-2-基、1,3,4-噻二唑-2-基、1,3,4-三唑-2-基,6-元杂芳基实例为2-吡啶基、3-吡啶基、4-吡啶基、2-哒嗪基、4-哒嗪基、2-嘧啶基、4-嘧啶基、5-嘧啶基、2-吡嗪基、1,3,5-三嗪-2-基、1,2,4-三嗪-3-基及1,2,4,5-四嗪-3-基,稠合的5-元杂芳基实例为苯并噻唑-2-基及苯并噁唑-2-基,稠合的6-元杂芳基实例为喹啉、异喹啉、喹唑啉及喹喔啉。
二价单元的定义是指饱和可经由单、双/或三键产生,因此二价单元“0”为经由两个单键连接的氧原子,二价单元“CRc”为经由一个单键及一个双键连接并含一个Rc基的碳原子,二价单元“C”为经由一个单键及一个三键连接的碳原子,如果存在一个不对称的二价单元,也就是说如果允许两种可能的连接,在各情形下连接此单元及其余分子的两种可能都包括在式I内。
决定于取代基的类型及连接,式(I)化合物可作为立体异构体存在,如果例如存在一或多个烯基,此可形成非对映异构体,如果例如存在一或多个非对称性碳原子,此可形成对映异构体及非对映异构体,经由惯用的分离方法,可从制备的混合物得到立体异构体,例如层析分离法,也可使用光学活性的起始物质及/或辅剂,通过使用立体选择性反应制备立体异构体,本发明也关于式(I)所包括但是没有特别定义的全部的立体异构体及其混合物。
所称的“部分或全部卤化”是指基团中的部分或全部的氢原子被上述相同或不同的卤原子取代。
如果一个基团经多取代,应当理解当组合不同的取代基时,必须注意到构成化学化合物的一般性原则,也就是说不形成本领域技术人员已知的在化学上不稳定或不可能的化合物。
其他有价值的式(I)化合物为其中
R1、R2、R3彼此独立地为氢、烷基、烯基、炔基、环烷基、环烯基、环烷基烷基、环烷基烯基、环烷基炔基、芳基、芳基烷基、芳基烯基、芳基炔基、杂芳基、杂芳基烷基、杂芳基烯基、杂芳基炔基、杂环基、杂环基烷基、杂环基烯基、杂环基炔基、羟基、烷氧基、烯氧基、炔氧基、环烷氧基、环烷基烷氧基、环烷基烯氧基、环烷基炔氧基、环烯氧基、芳氧基、芳基烷氧基、芳基烯氧基、芳基炔氧基、杂芳氧基、杂芳基烷氧基、杂芳基烯氧基、杂芳基炔氧基、杂环氧基、杂环烷氧基、杂环烯氧基、杂环炔氧基、硫基、烷硫基、烯硫基、炔硫基、环烷硫基、环烷基烷硫基、环烷基烯硫基、环烷基炔硫基、环烯基硫基、芳硫基、芳基烷硫基、芳基烯硫基、芳基炔硫基、杂芳基硫基、杂芳基烷硫基、杂芳基烯硫基、杂芳基炔硫基、杂环基硫基、杂环基烷硫基、杂环基烯硫基、杂环基炔硫基、氨基、未经取代或经取代的单-或二烷氨基、未经取代或经取代的单-或二芳氨基、未经取代或经取代的单-或二杂芳氨基、未经取代或经取代的N-烷基-N-芳基氨基、未经取代或经取代的N-烷基-N-杂芳基氨基、烯基氨基、炔基氨基、环烷基氨基、环烯基氨基、杂环烷基氨基、杂环烯基氨基、烷基磺酰基、烯基磺酰基、炔基磺酰基、环烷基磺酰基、环烷基烷基磺酰基、环烷基烯基磺酰基、环烷基炔基磺酰基、芳基磺酰基、芳基烷基磺酰基、芳基烯基磺酰基、芳基炔基磺酰基、杂芳基磺酰基、杂芳基烷基磺酰基、杂芳基烯基磺酰基、杂芳基炔基磺酰基、杂环基磺酰基、杂环基烷基磺酰基、杂环基烯基磺酰基、杂环基炔基磺酰基、烷基亚磺酰基、烯基亚磺酰基、炔基亚磺酰基、环烷基亚磺酰基、环烷基烷基亚磺酰基、环烷基烯基亚磺酰基、环烷基炔基亚磺酰基、芳基亚磺酰基、芳基烷基亚磺酰基、芳基烯基亚磺酰基、芳基炔基亚磺酰基、杂芳基亚磺酰基、杂芳基烷基亚磺酰基、杂芳基烯基亚磺酰基、杂芳基炔基亚磺酰基、杂环基亚磺酰基、芳基烷基亚磺酰基、杂环基烯基亚磺酰基、杂环基炔基亚磺酰基、氨基磺酰基、未经取代或经取代的单-或二烷氨基磺酰基、未经取代或经取代的单-或二芳氨基磺酰基、未经取代或经取代的单-或二杂芳氨基磺酰基、未经取代或经取代的N-烷基-N-芳基氨基磺酰基、未经取代或经取代的N-烷基-N-杂芳基氨基磺酰基、烷基磺酰氧基、烯基磺酰氧基、炔基磺酰氧基、环烷基磺酰氧基、环烷基烷基磺酰氧基、环烷基烯基磺酰氧基、环烷基炔基磺酰氧基、芳期磺酰氧基、芳基烷基磺酰氧基、芳基烯基磺酰氧基、芳基炔基磺酰氧基、杂芳基磺酰氧基、杂芳基烷基磺酰氧基、杂芳基烯基磺酰氧基、杂芳基炔基磺酰氧基、杂环基磺酰氧基、杂环基烷基磺酰氧基、杂环基烯基磺酰氧基、杂环基炔基磺酰氧基、烷基磺酰氨基、烯基磺酰氨基、炔基磺酰氨基、环烷基磺酰氨基、环烷基烷基磺酰氨基、环烷基烯基磺酰氨基、环烷基炔基磺酰氨基、芳基磺酰氨基、芳基烷基磺酰氨基、芳基烯基磺酰氨基、芳基炔基磺酰氨基、杂芳基磺酰氨基、杂芳基烷基磺酰氨基、杂芳基烯基磺酰氨基、杂芳基炔基磺酰氨基、烷基磺酰基-N-烷氨基、烯基磺酰基-N-烷氨基、炔基磺酰基-N-烷氨基、环烷基磺酰基-N-烷氨基、环烷基烷基磺酰基-N-烷氨基、环烷基烯基磺酰基-N-烷氨基、环烷基炔基磺酰基-N-烷氨基、芳基磺酰基-N-烷氨基、杂芳基磺酰基-N-烷氨基、芳基烷基磺酰基-N-烷氨基、杂芳基烷基磺酰基-N-烷氨基、芳基烯基磺酰氨基、杂芳基烯基磺酰氨基、芳基炔基磺酰基-N-烷氨基、杂芳基炔基磺酰基-N-烷氨基、杂环基磺酰基-N-烷氨基、杂环基烷基磺酰氨基、杂环基烯基磺酰基-N-烷氨基、杂环基炔基磺酰基-N-烷氨基、烷基羰基、烯基羰基、炔基羰基、环烷基羰基、环烷基烷基羰基、环烷基烯基羰基、环烷基炔基羰基、芳基羰基、芳基烷基羰基、芳基烯基羰基、芳基炔基羰基、杂芳基羰基、杂芳基烷基羰基、杂芳基烯基、杂芳基炔基羰基、杂环基羰基、杂环基烷基羰基、杂环基烯基、杂环基炔基羰基、羧基、烷氧羰基、烯氧羰基、炔氧羰基、环烷氧羰基、环烷基烷氧羰基、环烷基烯氧羰基、环烷基炔氧羰基、芳氧羰基、芳基烷氧羰基、芳基烯氧羰基、芳基炔氧羰基、杂芳氧羰基、杂芳基烷氧羰基、杂芳基烯氧羰基、杂芳基炔氧羰基、杂环氧羰基、杂环基烷氧羰基、杂环基烯氧羰基、杂环基炔氧羰基、氨基羰基、未经取代或经取代的单-或二烷基氨基羰基、未经取代或经取代的单-或二芳基氨基羰基、未经取代或经取代的单-或二杂芳基氨基羰基、未经取代或经取代的N-烷基-N-芳基氨基羰基、未经取代或经取代的N-烷基-N-杂芳基氨基羰基、未经取代或经取代的烷基羰基氨基、未经取代或经取代的烷基羰基-N-烷基氨基、未经取代或经取代的芳基羰基氨基、未经取代或经取代的芳基羰基-N-芳基氨基、未经取代或经取代的杂芳基羰基氨基、未经取代或经取代的杂芳基羰基-N-杂芳基氨基、未经取代或经取代的烷基羰基-N-芳基氨基、未经取代或经取代的芳基羰基-N-烷基氨基、未经取代或经取代的烷基羰基-N-杂芳基氨基、未经取代或经取代的杂芳基羰基-N-烷基氨基、烷氧羰基氨基、烯氧羰基氨基、炔氧羰基氨基、环烷氧羰基氨基、环烷基烷氧羰基氨基、环烷基烯氧羰基氨基、环烷基炔氧羰基氨基、芳氧羰基氨基、芳基烷氧羰基氨基、芳基烯氧羰基氨基、芳基炔氧羰基氨基、杂芳氧羰基氨基、杂芳基烷氧羰基氨基、杂芳基烯氧羰基氨基、杂芳基炔氧羰基氨基、杂环基氧羰基氨基、杂环基烷氧羰基氨基、杂环基烯氧羰基氨基、杂环基炔氧羰基氨基、烷氧羰基-N-烷基氨基、烯氧羰基-N-烷基氨基、炔氧羰基-N-烷基氨基、环烷氧羰基-N-烷基氨基、环烷基烷氧羰基-N-烷基氨基、环烷基烯氧羰基-N-烷基氨基、环烷基炔氧羰基-N-烷基氨基、芳氧羰基-N-烷基氨基、芳基烷氧羰基-N-烷基氨基、芳基烯氧羰基-N-烷基氨基、芳基炔氧羰基-N-烷基氨基、杂芳基烷氧羰基-N-烷基氨基、杂芳基烯氧羰基-N-烷基氨基、杂芳基炔氧羰基-N-烷基氨基、杂环基烷氧羰基-N-烷基氨基、杂环基烯氧羰基-N-烷基氨基、杂环基炔氧羰基-N-烷基氨基、甲酰基、卤素、卤烷基、卤烯基、卤炔基、卤烷氧基、卤烯氧基、卤炔氧基、卤烷硫基、卤烯硫基、卤炔硫基、卤烷氨基、卤烯氨基、卤炔氨基、卤烷磺酰基、卤烯磺酰基、卤炔磺酰基、卤烷亚磺酰基、卤烯亚磺酰基、卤炔亚磺酰基、卤烷基羰基、卤烯基羰基、卤炔基羰基、卤烷氧羰基、卤烯氧羰基、卤炔氧羰基、卤烷氨基羰基、卤烯氨基羰基、卤炔氨基羰基、卤烷氧羰基氨基、卤烯氧羰基氨基、卤炔氧羰基氨基、烷氧基烷氧基、芳基烷氧基烷氧基、氰基、硝基或选自烷基-NH-N=CH-、芳基-(CH2)n-NH-N=CH-、烷氧基-N=CH-、芳基-(CH2)n-O-N=CH-、烷基-NH-NH-CO-及芳烷基-NH-NH-CO-;且
R5为杂芳基、杂环基或芳基,它们各为未经取代或经选自下列的相同或不同的基单-或多取代,包括烷基、烯基、炔基、环烷基、环烯基、环烷基烷基、环烷基烯基、环烷基炔基、芳基、芳基烷基、芳基烯基、芳基炔基、杂芳基、杂芳基烷基、杂芳基烯基、杂芳基炔基、杂环基、杂环基烷基、杂环基烯基、杂环基炔基、羟基、烷氧基、烯氧基、炔氧基、环烷氧基、环烷基烷氧基、环烷基烯氧基、环烷基炔氧基、环烯氧基、芳氧基、芳基烷氧基、芳基烯氧基、芳基炔氧基、杂芳氧基、杂芳基烷氧基、杂芳基烯氧基、杂芳基炔氧基、杂环氧基、杂环烷氧基、杂环烯氧基、杂环炔氧基、硫基、烷硫基、烯硫基、炔硫基、环烷硫基、环烷基烷硫基、环烷基烯硫基、环烷基炔硫基、环烯基硫基、芳硫基、芳基烷硫基、芳基烯硫基、芳基炔硫基、杂芳基硫基、杂芳基烷硫基、杂芳基烯硫基、杂芳基炔硫基、杂环基硫基、杂环基烷硫基、杂环基烯硫基、杂环基炔硫基、氨基、未经取代或经取代的单-或二烷氨基、未经取代或经取代的单-或二芳氨基、未经取代或经取代的单-或二杂芳氨基、未经取代或经取代的N-烷基-N-芳基氨基、未经取代或经取代的N-烷基-N-杂芳基氨基、烯基氨基、炔基氨基、环烷基氨基、环烯基氨基、杂环烷基氨基、杂环烯基氨基、烷基磺酰基、烯基磺酰基、炔基磺酰基、环烷基磺酰基、环烷基烷基磺酰基、环烷基烯基磺酰基、环烷基炔基磺酰基、芳基磺酰基、芳基烷基磺酰基、芳基烯基磺酰基、芳基炔基磺酰基、杂芳基磺酰基、杂芳基烷基磺酰基、杂芳基烯基磺酰基、杂芳基炔基磺酰基、杂环基磺酰基、杂环基烷基磺酰基、杂环基烯基磺酰基、杂环基炔基磺酰基、烷基亚磺酰基、烯基亚磺酰基、炔基亚磺酰基、环烷基亚磺酰基、环烷基烷基亚磺酰基、环烷基烯基亚磺酰基、环烷基炔基亚磺酰基、芳基亚磺酰基、芳基烷基亚磺酰基、芳基烯基亚磺酰基、芳基炔基亚磺酰基、杂芳基亚磺酰基、杂芳基烷基亚磺酰基、杂芳基烯基亚磺酰基、杂芳基炔基亚磺酰基、杂环基亚磺酰基、芳基烷基亚磺酰基、杂环基烯基亚磺酰基、杂环基炔基亚磺酰基、氨基磺酰基、未经取代或经取代的单-或二烷氨基磺酰基、未经取代或经取代的单-或二芳氨基磺酰基、未经取代或经取代的单-或二杂芳氨基磺酰基、未经取代或经取代的N-烷基-N-芳基氨基磺酰基、未经取代或经取代的N-烷基-N-杂芳基氨基磺酰基、烷基磺酰氧基、烯基磺酰氧基、炔基磺酰氧基、环烷基磺酰氧基、环烷基烷基磺酰氧基、环烷基烯基磺酰氧基、环烷基炔基磺酰氧基、芳基磺酰氧基、芳基烷基磺酰氧基、芳基烯基磺酰氧基、芳期炔基磺酰氧基、杂芳基磺酰氧基、杂芳基烷基磺酰氧基、杂芳基烯基磺酰氧基、杂芳基炔基磺酰氧基、杂环基磺酰氧基、杂环基烷基磺酰氧基、杂环基烯基磺酰氧基、杂环基炔基磺酰氧基、烷基磺酰氨基、烯基磺酰氨基、炔基磺酰氨基、环烷基磺酰氨基、环烷基烷基磺酰氨基、环烷基烯基磺酰氨基、环烷基炔基磺酰氨基、芳基磺酰氨基、芳基烷基磺酰氨基、芳基烯基磺酰氨基、芳基炔基磺酰氨基、杂芳基磺酰氨基、杂芳基烷基磺酰氨基、杂芳基烯基磺酰氨基、杂芳基炔基磺酰氨基、烷基磺酰基-N-烷氨基、烯基磺酰基-N-烷氨基、炔基磺酰基-N-烷氨基、环烷基磺酰基-N-烷氨基、环烷基烷基磺酰基-N-烷氨基、环烷基烯基磺酰基-N-烷氨基、环烷基炔基磺酰基-N-烷氨基、芳基磺酰基-N-烷氨基、杂芳基磺酰基-N-烷氨基、芳基烷基磺酰基-N-烷氨基、杂芳基烷基磺酰基-N-烷氨基、芳基烯基磺酰基-N-烷氨基、杂芳基烯基磺酰基-N-烷氨基、芳基炔基磺酰基-N-烷氨基、杂芳基炔基磺酰基-N-烷氨基、杂环基磺酰基-N-烷氨基、杂环基烷基磺酰基-N-烷氨基、杂环基烯基磺酰基-N-烷氨基、杂环基炔基磺酰基-N-烷氨基、烷基羰基、烯基羰基、炔基羰基、环烷基羰基、环烷基烷基羰基、环烷基烯基羰基、环烷基炔基羰基、芳基羰基、芳基烷基羰基、芳基烯基羰基、芳基炔基羰基、杂芳基羰基、杂芳基烷基羰基、杂芳基烯基、杂芳基炔基羰基、杂环基羰基、杂环基烷基羰基、杂环基烯基、杂环基炔基羰基、羧基、烷氧羰基、烯氧羰基、炔氧羰基、环烷氧羰基、环烷基烷氧羰基、环烷基烯氧羰基、环烷基炔氧羰基、芳氧羰基、芳基烷氧羰基、芳基烯氧羰基、芳基炔氧羰基、杂芳氧羰基、杂芳基烷氧羰基、杂芳基烯氧羰基、杂芳基炔氧羰基、杂环氧羰基、杂环基烷氧羰基、杂环基烯氧羰基、杂环基炔氧羰基、氨基羰基、未经取代或经取代的单-或二烷基氨基羰基、未经取代或经取代的单-二芳基氨基羰基、未经取代或经取代的单-或二杂芳基氨基羰基、未经取代或经取代的N-烷基-N-芳基氨基羰基、未经取代或经取代的N-烷基-N-杂芳基氨基羰基、未经取代或经取代的烷基羰基氨基、未经取代或经取代的烷基羰基-N-烷基氨基、未经取代或经取代的芳基羰基氨基、未经取代或经取代的芳基羰基-N-芳基氨基、未经取代或经取代的杂芳基羰基氨基、未经取代或经取代的杂芳基羰基-N-杂芳基氨基、未经取代或经取代的烷基羰基-N-芳基氨基、未经取代或经取代的芳基羰基-N-烷基氨基、未经取代或经取代的烷基羰基-N-杂芳基氨基、未经取代或经取代的杂芳基羰基-N-烷基氨基、烷氧羰基氨基、烯氧羰基氨基、炔氧羰基氨基、环烷氧羰基氨基、环烷基烷氧羰基氨基、环烷基烯氧羰基氨基、环烷基炔氧羰基氨基、芳氧羰基氨基、芳基烷氧羰基氨基、芳基烯氧羰基氨基、芳基炔氧羰基氨基、杂芳氧羰基氨基、杂芳基烷氧羰基氨基、杂芳基烯氧羰基氨基、杂芳基炔氧羰基氨基、杂环氧羰基氨基、杂环基烷氧羰基氨基、杂环基烯氧羰基氨基、杂环基炔氧羰基氨基、烷氧羰基-N-烷基氨基、烯氧羰基-N-烷基氨基、炔氧羰基-N-烷基氨基、环烷氧羰基-N-烷基氨基、环烷基烷氧羰基-N-烷基氨基、环烷基烯氧羰基-N-烷基氨基、环烷基炔氧羰基-N-烷基氨基、芳氧羰基-N-烷基氨基、芳基烷氧羰基-N-烷基氨基、芳基烯氧羰基-N-烷基氨基、芳基炔氧羰基-N-烷基氨基、杂芳基烷氧羰基-N-烷基氨基、杂芳基烯氧羰基-N-烷基氨基、杂芳基炔氧羰基-N-烷基氨基、杂环基烷氧羰基-N-烷基氨基、杂环基烯氧羰基-N-烷基氨基、杂环基炔氧羰基-N-烷基氨基、甲酰基、卤素、卤烷基、卤烯基、卤炔基、卤烷氧基、卤烯氧基、卤炔氧基、卤烷硫基、卤烯硫基、卤炔硫基、卤烷氨基、卤烯氨基、卤炔氨基、卤烷磺酰基、卤烯磺酰基、卤炔磺酰基、卤烷亚磺酰基、卤烯亚磺酰基、卤炔亚磺酰基、卤烷基羰基、卤烯基羰基、卤炔基羰基、卤烷氧羰基、卤烯氧羰基、卤炔氧羰基、卤烷氨基羰基、卤烯氨基羰基、卤炔氨基羰基、卤烷氧羰基氨基、卤烯氧羰基氨基、卤炔氧羰基氨基、烷氧基烷氧基、芳基烷氧基烷氧基、氰基、硝基或选自烷基-NH-N=CH-、芳基-(CH2)n-NH-N=CH-、烷氧基-N=CH-、芳基-(CH2)n-O-N=CH-、烷基-NH-NH-CO-及芳烷基-NH-NH-CO-;或为选自-O-N=CRlRm、-P(=O)(ORi)(Rj)、-P(=O)(ORi)(ORk)或下式的基
或如果E为一个键且l为0时,R5也可为羟基。
特别有价值的式(I)化合物为其中
R1、R2、R3彼此独立地为氢、卤素、硝基、氰基、烷基、环烷基、烯基、炔基、烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、烷基磺酰氧基、烷基磺酰氨基、烷基磺酰基-N-烷氨基、苯基、苄基,其中最后提到的十三种基团为未经取代或经一或多个选自卤素、硝基、氰基、烷基、卤烷基、环烷基、烯基、炔基、烷氧基、卤烷氧基及烷硫基的相同或不同基取代;
R4为氢、氰基、烷基、烯基、炔基、环烷基,其中四种最后提到的基团为未经取代或经一或多个选自卤素、硝基、氰基、烷基、环烷基、炔基、烷氧基及烷硫基的相同或不同的基团取代;
R5为苯基、三-、五-或六-元杂芳基,其可含至多三个选自氮、氧及硫的杂原子,或为三-至六-元饱和、部分饱和或不饱和的杂环基,其可含至多四个选自氮、氧及硫的杂原子,它们各为未经取代或经选自下列的相同或不同的基单-或多取代,包括卤素、硝基、氰基、甲酰基、氨基、苯基、苄基、(C1-C6)-烷基、(C2-C6)-烯基、(C2-C6)-炔基、(C3-C6)-环烷基、(C1-C6)-烷氧基、(C1-C6)-烷氨基、二-(C1-C6)-烷氨基、(C1-C6)-烷氧羰基、(C1-C6)-烷氨基羰基、二-(C1-C6)-烷氨基羰基、(C1-C6)-烷基羰基、(C1-C6)-烷基羰基氨基、(C1-C6)-烷基羰基-(C1-C6)-烷氨基、(C1-C6)-烷基羰基-二-(C1-C6)-烷基氨基、(C1-C6)-烷基硫基、(C1-C6)-烷基亚磺酰基、(C1-C6)-烷基磺酰基、(C1-C6)-烷基磺酰基氨基、(C1-C6)-烷基磺酰基-(C1-C6)-烷基氨基、(C1-C6)-烷基磺酰基-二-(C1-C6)-烷基氨基,其中22种最后提到的基团为未经取代或经一或多个选自卤素、硝基、氰基、(C1-C6)-烷基、(C3-C6)-环烷基、(C2-C6)-烯基、(C2-C6)-炔基、(C1-C6)-烷氧基、(C1-C6)-烷硫基或三-至六-元饱和、部分饱和或不饱和且含至多四个选自氮、氧及硫的杂原子的杂环基的相同或不同的基团取代;或为选自-O-N=CRlRm、-P(=O)(ORi)(Rj)、-P(=O)(ORi)(ORk)或下式的基团
或如果E为一个键且l为0时,R5也可为羟基;
A为选自S、SO、SO2及NRa的二价单元;
B为含一或两个碳原子的链,其为饱和或含一个双键且其为未经取代或经烷基、卤烷基、烷氧基或卤烷氧基取代;
E为一个键、CRcRd、NRc、S、SO、SO2、O及OO;
R6为(C1-C6)-烷硫基、(C1-C6)-烷亚磺酰基、(C1-C6)-烷磺酰基、氰基、氰氧基、氰硫基、卤素或ORf;
Y为选自O、S、N-(C1-C6)-烷基或CHR7的二价单元;
R7为氢、(C1-C6)-烷基、(C3-C8)-环烷基、(C1-C6)-烷氧基、(C1-C6)-烷氧基-(C1-C6)-烷基、(C1-C6)-烷羰基、(C1-C6)-烷氧羰基、(C1-C6)-烷硫基、苯基,其中八种最后提到的基团的烃基部分为未经取代或经一或多个选自卤素、(C1-C3)-烷硫基及(C1-C3)-烷氧基的相同或不同的基团取代;
Z为一个键、CH2或CHR7;
R8为氢、(C1-C6)-烷基或(C1-C6)-烷氧羰基;
R9为氢、(C1-C6)-烷基、(C3-C8)-环烷基或卤代-(C1-C6)-烷基;
R10为氢、(C1-C6)-烷基、(C2-C6)-烯基、(C1-C6)-炔基、(C3-C8)-环烷基、苯基、苄基,其中六种最后提到的基团为未经取代或经一或多个选自卤素、氰基、硝基及(C1-C6)-烷氧基的相同或不同的基团取代;
R11为氢、甲酰基、(C1-C6)-烷基、卤代-(C1-C6)-烷基、(C1-C6)-烷氧基-(C1-C6)-烷基或L-R12基;
L为选自SO2、CO及CHRgCO的二价单元;
R12为(C1-C6)-烷基、卤代-(C1-C6)-烷基或为苯基,其为未经取代或经一或多个选自氰基、硝基、(C1-C3)-烷基、(C1-C3)-烷氧基、卤代-(C1-C3)-烷基及卤代-(C1-C3)-烷氧基的相同或不同的基团取代;
Ra为氢、卤素、氰基、硝基、甲酰基、(C1-C6)-烷基、(C3-C8)-环烷基、(C2-C6)-烯基、(C2-C6)-炔基、(C1-C6)-烷基羰基及(C1-C6)-烷基磺酰基,其中六种最后提到的基团的烃基部分为未经取代或经一或多个选自卤素、硝基、氰基、(C1-C6)-烷基、(C3-C8)-环烷基、(C2-C6)-烯基、(C2-C6)-炔基、(C1-C6)-烷氧基及(C1-C6)-烷硫基的相同或不同的基团取代;
Rc及Rd彼此独立地为氢、卤素、硝基、氰基、(C1-C6)-烷基、卤代-(C1-C6)-烷基、(C3-C8)-环烷基、(C2-C6)-烯基、卤代-(C2-C6)-烯基、(C2-C6)-炔基、卤代-(C2-C6)-炔基、(C1-C6)-烷氧基、卤代-(C1-C6)-烷氧基、(C1-C6)-烷硫基、卤代-(C1-C6)-烷硫基、(C1-C6)-烷基羰基、卤代-(C1-C6)-烷基羰基、(C1-C6)-烷氧羰基、卤代-(C1-C6)-烷氧羰基、氨基羰基、(C1-C6)-烷基羰基及(C1-C6)-烷基磺酰基;
Re为氢、甲酰基、(C1-C6)-烷基、(C3-C8)-环烷基、(C2-C6)-烯基、(C2-C6)-炔基、(C1-C6)-烷基羰基及(C1-C6)-烷基磺酰基,其中六种最后提到的基团的烃基部分为未经取代或经一或多个选自卤素、硝基、氰基、(C1-C6)-烷基、环烷基、(C2-C6)-烯基、(C2-C6)-(C1-C6)-炔基、(C1-C6)-烷氧基及(C1-C6)-烷硫基的相同或不同的基团取代;
Rf为氢、(C1-C6)-烷基、卤代-(C1-C6)-烷基、(C1-C6)-烷基羰基、(C1-C6)-烷氧羰基、(C1-C6)-烷基磺酰基、卤代-(C1-C6)-烷基磺酰基、苯甲酰基或苯基磺酰基,其中两种最后提到的基团的芳族部分为未经取代或经一或多个选自(C1-C6)-烷基、卤代-(C1-C6)-烷基、(C1-C6)-烷氧基、卤代-(C1-C6)-烷氧基、卤素、氰基及硝基的相同或不同的基团取代;
Rg及Rh彼此独立地为氢或(C1-C6)-烷基;且
w为0、1、2或3。
优选的式I化合物为其中
R1、R2、R3彼此独立地为为氢、卤素、硝基、氰基、(C1-C6)-烷基、(C3-C8)-环烷基、(C2-C6)-烯基、(C2-C6)-炔基、(C1-C6)-烷氧基、(C1-C6)-烷硫基、(C1-C6)-烷基亚磺酰基、(C1-C6)-烷基磺酰基、(C1-C6)-烷基磺酰氧基、(C1-C6)-烷基磺酰氨基、(C1-C6)-烷基磺酰基-N-(C1-C6)-烷氨基、苯基、苄基,其中最后提到的十三种基为未经取代或经一或多个选自卤素、硝基、氰基、(C1-C3)-烷基、卤代-(C1-C3)-烷基、环丙基、(C2-C4)-烯基、(R2-C4)-炔基、(C1-C3)-烷氧基、卤代-(C1-C3)-烷氧基及烷硫基的相同或不同的基团取代;
R4为(C1-C4)烷基、氢、氰基、(C2-C4)-烯基、(C2-C4)-炔基、(C3-C6)-环烷基,其中三种最后提到的基团为未经取代或经一或多个选自卤素、氰基、(C1-C3)-烷氧基、(C1-C3)-烷硫基的相同或不同的基团取代,且第一个提到的基团为未经取代或经一或多个选自卤素、氰基、(C3-C6)-环烷基、(C1-C3)-烷氧基、(C1-C3)-烷硫基的相同或不同的基团取代;
R5为苯基、三-、五-或六-元杂芳基,其可含至多三个选自氮、氧及硫的杂原子,或为三-至六-元饱和、部分饱和或不饱和的杂环基,其可含至多四个选自氮、氧及硫的杂原子,它们各为未经取代或经选自下列的相同或不同的基团单-或多取代,包括卤素、硝基、氰基、甲酰基、氨基、苯基、苄基、(C1-C4)烷基、(C2-C4)-烯基、(C2-C4)-炔基、(C3-C6)-环烷基、(C1-C4)烷氧基、(C1-C4)烷氨基、二-(C1-C4)烷氨基、(C1-C4)烷氧羰基、(C1-C4)烷氨基羰基、二-(C1-C4)烷氨基羰基、(C1-C4)烷基羰基、(C1-C4)烷基羰基氨基、(C1-C4)烷基硫基、(C1-C4)烷基亚磺酰基、(C1-C4)烷基磺酰基;或为选自-O-N=CRlRm、-P(=O)(ORi)(Rj)、-P(=O)(ORi)(ORk)或下式的基团
或如果E为一个键且l为0时,R5也可为羟基;
A为选自S、SO及SO2的二价单元;
B为含一或两个碳原子的链,其为饱和或含一个双链且其为未经取代或经一或两个相同或不同的选自(C1-C3)-烷基、卤代-(C1-C3)-烷基、(C1-C3)-烷氧基或卤代-(C1-C3)-烷氧基的基团取代;
E为一个键、CRcRd、SO2及CO;
R6为(C1-C3)-烷硫基、(C1-C3)-烷磺酰基、氰基、氰氧基、氰硫基、卤素或ORf;
Y为选自O及CHR7的二价单元;
R7为氢、(C1-C6)-烷基、(C3-C8)-环烷基、(C1-C6)-烷氧基-(C1-C6)-烷基、(C1-C6)-烷羰基、(C1-C6)-烷氧羰基、苯基,其中六种最后提到的基团为未经取代或经一或多个相同或不同的卤素原子取代;
R9为(C1-C6)-烷基、(C3-C6)-环烷基或卤代-(C1-C6)-烷基;
R10为(C1-C6)-烷基、(C2-C6)-烯基、(C2-C6)-炔基、(C3-C8)-环烷基、苯基或苄基;
R11为氢、(C1-C6)-烷基或L-R12基;
Rc及Rd彼此独立地为氢,(C1-C3)-烷基、卤代-(C1-C3)烷基、(C2-C6)-烯基、卤代-(C2-C6)-烯基、(C2-C6)-炔基、卤代-(C2-C6)-炔基、(C1-C3)烷氧基、卤代-(C1-C3)烷氧基、(C1-C3)烷硫基、卤代-(C1-C3)烷硫基及(C1-C3)-烷基羰基;
Rf为氢、(C1-C6)-烷基、(C1-C6)-烷基羰基、(C1-C6)-烷氧羰基、(C1-C6)-烷基磺酰基、苯甲酰基或苯基磺酰基,其中两种最后提到的基团的芳族部分为未经取代或经一或多个选自(C1-C6)-烷基、卤代-(C1-C6)-烷基、(C1-C6)-烷氧基、卤代-(C1-C6)-烷氧基、卤素、氰基及硝基的相同或不同的基团取代;
w为0、1或2。
也优选式I化合物,其中Q为式(II)或(III)的基团
特别优选式I化合物,其中
R1及R2彼此独立地为氢、(C1-C4)烷基、卤素或硝基;
R3及R4为氢;
A为SO2;
B为CH2-CH2;
E为一个键或选自CH2、CO及SO2的二价单元;
R6为ORf;
Y为CHR7;
Z为CHR7;
G1-G2为选自OCR9及NR10COR11的二价单元;
R7为氢或(C1-C6)-烷基;
R8为氢;
R9为(C3-C6)-环烷基;
R10为(C1-C3)烷基;
R11为氢或L-R12基;
L为选自SO2、CO及CH2CO的二价单元;
R12为苯基,其未经取代或经一或多个选自卤素、氰基、硝基、(C1-C6)-烷基、(C1-C6)-烷氧基、(C1-C6)-卤烷基及(C1-C6)-卤烷氧基的相同或不同的基团取代;
Re为氢、甲酰基、(C1-C6)-烷基、(C2-C6)-烯基、(C2-C6)-炔基、(C1-C6)-烷基羰基及(C1-C6)-烷基磺酰基;
Rf为氢、(C1-C6)-烷基磺酰基、苯甲酰基、苯基磺酰基、其中两种最后提到的基团为未经取代或经一或多个选自(C1-C6)-烷基、(C1-C6)-卤烷基、(C1-C6)-烷氧基、(C1-C6)-卤烷氧基、卤素、氰基及硝基的相同或不同的基团取代;且
v为1。
非常特别优选式I化合物,其中Q为式(II)的基团
非常特别优选的式I化合物也可为其中
R5为苯基、三-、五-或六元杂芳基,其可含至多三个选自氮、氧及硫的杂原子,或为三-至六-元、部分饱和或不饱和的杂环基,其可含一、二、三或四个选自氮、氧及硫的杂原子,它们各为未经取代或经选自下列的相同或不同的基团单-或多取代,包括卤素、硝基、氰基、甲酰基、氨基、苯基、苄基、(C1-C4)烷基、(C2-C4)-烯基、(C2-C4)-炔基、(C3-C6)-环烷基、(C1-C4)烷氧基、(C1-C4)烷氨基、二-(C1-C4)烷氨基、(C1-C4)烷氧羰基、(C1-C4)烷氨基羰基、二-(C1-C4)烷氨基羰基、(C1-C4)烷基羰基、(C1-C4)烷基羰基氨基、(C1-C4)烷基硫基、(C1-C4)烷基亚磺酰基、(C1-C4)烷基磺酰基。
决定于取代基的定义,根据本发明的化合物可根据一或多个下列流程中陈述的方法例如从已知或可用已知方法制备的式(Ia)化合物制备。
流程1说明式(Ic)化合物与乙二醇的酸催化反应,得到式(Id)化合物,随后与正丁基锂或镁、二氧化碳反应,且随后用酸处理后得到式(Ie)化合物,其中R为OH,此反应为已知,例如从有机化学杂志(J.Org.Chem.)55,773(1990)已知,经由惯用的酯化反应,可将此化合物转化成式(Ie)的对应酯类,其中R为烷氧基,在下列全部的化学式中,除非特别说明,取代基相同于式(I)中所提的定义。
流程1:
R为烷氧基的式(Ie)化合物可根据流程2经由多个反应在苯并稠合的羰基上官能基化,此反应为已知,例如从Houben-Weyl,有机化学方法(“Methoden der organischen Chemie”),volume 7,paRf 2b,Georg-Thieme Verlag,StuttgaRf,1965。
流程2
2.1 与还原剂例如NaBH4反应,形成式(If)化合物,其中X为氧且R4为氢。
2.2 与格利雅试剂反应,形成式(If)化合物,其中X为氧且R4为烷基、烯基、炔基、环烷基或苯基。
2.3 与Me3SiCN或Me3SiCF3反应,形成式(If)化合物,其中X为氧且R4为CN或CF3。
2.4 在氯化铵存在下与碱金属氰化物反应,形成式(If)化合物,其中X为NH且R4为CN。
2.5 在醋酸铵存在下与NaBH3CN反应,形成式(If)化合物,其中X为NH且R4为氢。
2.6 与P4S10反应,且随后与格利雅试剂反应,形成式(If)化合物,其中X为硫且R4为烷基、烯基、炔基、环烷基或苯基。
2.7 与H2N-E-R5反应,且随后还原,形成式(Ig)化合物,其中(X)1为NH且R4为氢。
2.8 与H2N-E-R5反应,且随后与格利雅试剂反应,形成式(Ig)化合物,其中(X)1为NH且R4为CN。
2.9 与H2N-E-R5及KCN反应,同样形成式(Ig)化合物,其中(X)1为NH且R4为CN。
2.10 在LiCN存在下,在THF中与(RiO)(RkO)(O=)PCN反应,形成式(Ig)化合物,其中l为0且E为一个键,R4为CN且R5为P(=O)(ORi)(ORk)。
如流程3中说明,式(Ig)化合物也可得自式(If)化合物,其中R为烷氧基,此反应为已知,例如从药物化学杂志(J.Med.Chem.)28,1817,(1985),四面体通讯(Tetrahedron Lett.)1699,(1986)及斯堪的纳维亚化学学报(Acta Chem.Scand.)B32,452(1978)已知。
流程3:
3.1 与氯化剂例如亚硫酰氯反应,且随后与式HNRa-E-R5的胺反应,形成式(Ig)化合物,其中(X)1为NRa且R4为氢。
3.2 与氯化剂例如亚硫酰氯反应,且随后与式HO-E-R5的醇反应,形成式(Ig)化合物,其中(X)1为氧且R4为氢。
3.3 与氯化剂例如亚硫酰氯反应,且随后与式HS-E-R5的硫醇反应,形成式(Ig)化合物,其中(X)1为硫且R4为氢。
3.4 与卤化物、三氟甲基磺酸盐或甲基磺酸盐反应,形成式(Ig)化合物,其中(X)1为氧且R4为氢。
3.5 在脱水剂例如DCC存在下,与羧酸反应,形成式(Ig)化合物,其中(X)1为氧,E为CO且R4为氢。
3.6 与氯化剂例如CCl4/PPh3反应,且随后与P(ORi)3反应,形成式(Ig)化合物,其中l为0且E为一个键,R4为氢且R5为P(=O)(ORi)(ORk)。
3.7 与氯化剂例如CCl4/PPh3反应,且随后与NaCN在溶剂例如DMF或DMSO中反应,形成式(Ig)化合物,其中R5为氰基,其可经由本领域技术人员已知的衍生化作用而反应,得到式(Ig)化合物,其中R5为-COOH、-COOR、-COCl、-CH=NOH或-CHO,起始自这些最后提到的化合物(Ig),可经由本领域技术人员已知的方法,制备根据本发明的式(I)化合物,其中R5为杂芳基或杂环基,其各经由碳原子连接。
3.8 与氯化剂例如CCl4/PPh3反应,且随后与氮环原子带有氢原子的杂芳族化合物或杂环碱性催化反应,形成式(Ig)化合物,其中l为0且E为一个键,R4为氢且R5为经由氮原子连接的杂芳基或杂环基。
3.9 与氯化剂例如草酰氯或CCl4/PPh3反应,且随后与化合物HO-N=RkRl在碱例如NaH存在下,在合适的溶剂例如THF、DMF或DMSO中反应,形成式(Ig)化合物,其中(X)1-E一起代表一个键,R4为氢且R5为-O-N=RkRl。
陈述在流程4的式(Ig)化合物与式(IIa)化合物的反应得到式Ia’化合物,其中Q为式(II)的基,为此,式(Ig)化合物在脱水剂例如DCC存在下或转化成其酰基氯后,与式(IIa)化合物经碱催化反应,且随后用氰化物源处理,这些方法揭示在例如EP-A 0 369 803及EP-B 0 283 261中,在这些化学式及下列化学式中,R为烷氧基。
流程4:
在流程5中说明的式(Ig)化合物与式(IIIa)羟基吡唑的反应得到根据本发明的化合物,其中Q为式(III)的基且G1-G2为NR10OCR11,为此,式(Ig)化合物在脱水剂例如DCC存在下或转化成其酰基氯后,与式(IIIa)经碱催化反应,且随后用氰化物源处理,这些方法揭示在例如EP-A 0 369803,经由已知的反应例如酯化、烷基化或酰化,将R11基引入吡唑环上。
流程5
在流程6中说明的式(Ig)化合物与β-酮酯的反应,且随后酸分解后得到式(Ih)化合物,经由与原羧酸酯或羧酰胺缩醛的反应,将其转化成式(Ii)化合物,其中L1为离去基团例如乙氧基或N,N-二甲氨基,最后,经由与羟基胺的碱催化反应,得到根据本发明的化合物(Ib’),其中Q为式(III)的基且G1-G2为OCR9。
流程6
在流程7中说明的式(Ig)化合物在镁、有机镁化合物或有机锂化合物存在下,与可经由例如根据合成通讯(Synth.Commun.)17,1207(1987)的方法制备的卤素取代的异噻唑反应,得到根据本发明的化合物(Ib″),其中Q为式(III)的基且G1-G2为SCR9。
流程7
在流程8中说明的其中R为氯的式(Ig)化合物与式(IVa)β-酮腈的碱催化反应,得到根据本发明的化合物(Ic),其中Q为式(IVI)的基,此反应是例如类似于EP-A 0 213 892及EP-A 0 496 631的方法进行。
流程8:
在流程9中说明的式(Ia’)化合物与卤化剂例如草酰氯或草酰溴的反应,形成根据本发明的式(Ia″)化合物,其可经由与亲核剂例如碱金属氰化物、碱金属氰酸盐、碱金属硫代氰酸盐、烷基硫醇及硫酚反应,如果适当时用碱催化,将其转化成根据本发明的其他式(Ia)化合物,此反应揭示在例如合成(Synthesis)12,1287(1992)。
流程9
其中A为硫的式(If)化合物可根据流程10使用合适的氧化剂例如过氧醋酸、过氧化氢、间氯过苯甲酸及过氧单硫酸钾氧化,得到相对应的化合物,其中决定于氧化剂的用量,A为SO或SO2,此反应为已知,例如从J.Org.Chem.53,532(1988)已知,且也可适用在本文提到的其他化合物。
流程10:
本发明也提供式(Ig)化合物
其中
R为(C1-C6)-烷基,
R4为氢,
R5为COOH、COOR、COCl、CH=NOH、CHO,
E为一个键,
l为0,
且R1、R2、R3、A及B具有在式(I)中的定义。
根据本发明的式(I)化合物对广谱的具有重要经济性的单子叶及双子叶有害植物具有极佳的除草活性,该活性化合物对从地下茎、根茎或其他多年生器官发芽且难于控制的多年生杂草也可有效地作用,在本案中是否在播种前、发芽前或发芽后使用该物质并不重要。具体而言,能列举出部分代表性的单子叶及双子叶杂草实例,可用根据本发明的化合物加以控制,但并不表示仅限于所列举的物种。
该活性物质可有效作用的杂草种类的实例为:单子叶杂草类如一年生草类如燕麦、毒麦属、看麦娘属、虉草属、稗属、马唐属、狗尾草属及莎草属,及多年生草类如冰草属、狗牙根属、白茅属及高粱属、及多年生的莎草属。在双子叶杂草类的情形下,作用范围可延伸至例如一年生的猪殃殃属、堇菜属、婆婆纳属、野芝麻属、繁缕属、苋属、欧白芥属、番薯属、母菊属、苘麻属及黄花稔属,及多年生草类如旋花属、蓟属、如酸模属及蒿属。
根据本发明的活性成份对于发生在稻米成长的特定情形下的杂草也有杰出的控制效果,例如稗属、慈姑属、泽泻属、荸荠属、藨草属及莎草属。
如果在发芽前先将根据本发明的化合物施加于土壤表面上,则可完全防止杂草幼苗的发芽,或者是杂草成长至子叶阶段后停止成长,最后经过三至四周后完全死亡。
如果活性化合物是在发芽后施加至植物的绿色部分时,处理后极短时间内成长也将彻底停止,杂草植物保持在施加时的成长阶段,或者是经一段时间后完全死亡,所以在这种方法中由于杂草的竞争所造成的对作物植物的伤害,可在极早阶段及以持久的方式将其消除。
虽然根据本发明的化合物对单子叶及双子叶杂草有极佳的除草活性,其对具有重要经济性的作物例如小麦、大麦、裸麦、稻米、玉米、甜菜、棉花及大豆等所造成的伤害只达可忽略的程度或根本不会造成伤害。基于这些理由,本发明化合物非常适于在农业上有用植物或观赏植物的种植中供选择性地控制不需要的植物生长。
由于其除草及植物生长调节的性质,此活性化合物也可在已知或仍在发展的基因工程改变的植物中用于供控制有害的植物,转基因的植物通常具有特别有利的性质,例如耐某种农药,尤其是某种除草剂,耐植物病或植物病的致病微生物,例如某种昆虫或微生物例如真菌、细菌或病毒,其他特定的性质涉及例如数量、品质、储存稳定性、收成产物的组成及特定的成份,因此,已知转基因的植物具有增加淀粉含量或改良淀粉品质或具有不同脂肪酸组成的收成产物。
优选根据本发明的式(I)化合物或其盐类在有用及观赏植物的重要经济性的转基因作物上的用途,例如在谷类例如小麦、大麦、裸麦、燕麦、黍、稻米、木薯及玉米、或在甜菜、棉花、大豆、油菜籽、马铃薯、番茄、豌豆及其他蔬菜,式(I)化合物优选在这样的有用植物的栽培中作为除草剂,其对除草剂或经由基因工程使对除草剂的植物毒性效应具有抵抗性。
与已知植物相比较具有改进特性的新植物的常规繁殖方法包括,例如,传统的育种方法和产生变种。另外,具有改进特性的新植物可以通过基因工程方法繁殖(参见,例如,EP-A-0 221 044,EP-A 0 131 624)。
例如,已公开的几种情况是
-对作物进行基因工程改造以改进植物中的淀粉合成(例如WO92/11376,WO 92/14827,WO 91/19806),
-抗草铵膦类(参见例如EP-A-0 242 236,EP-A-242 246)或草甘膦类(WO 92/00377)或磺酰脲类除草剂(EP-A 0 257 993,US-A 5013659)的转基因作物,
-可产生苏云金芽孢杆菌毒素(Bt毒素)的转基因作物,例如棉花,这可以使该植物产生对某些害虫的抗性(EP-A 0 142 924,EP-A0 193259),
-具有改进脂肪酸组成的转基因作物(WO 91/13972)。
原则上已知的很多分子生物学技术都可应用于生产新的具有改进特性的转基因植物;参见,例如,Sambrook等,1989,分子克隆,试验手册,第2版,Cold Spring Harbor Laboratory Press,Cold SpringHarbor,NY;或Winnacker“Gene und Klone”(基因与克隆),VCHWeinheim,第2版,1996或Christou,“Trends in Plant Science”(植物科学趋势)1(1996)第423-431页。
为进行这种基因工程操作,可以将核酸分子导入质粒中,这使得可以通过DNA序列重组方法发生基因突变或序列改变。使用上述标准方法可以例如,交换碱基,缺失部分序列或插入天然或合成序列。为互相连接DNA片段,可以将连接物或衔接物连接到片段上。
例如可以通过表达至少一个相应的反义-RNA,有义-RNA以获得共抑作用,或通过表达至少一个相应的特异性裂解上述基因产物的转录物的构建核酶来制备具有降低基因产物活性的植物细胞。
为此目的既可以使用包括基因产物的全部编码序列的DNA分子,该分子包括可能存在的侧翼序列,还可以使用仅包括部分编码序列的DNA分子,但这些部分必须足够长以在细胞中可获得反义效果。还可以使用与基因产物的编码序列具有高度同源性但并不完全相同的DNA序列。
当植物中的核酸分子进行表达时,可将合成的蛋白质定位于植物细胞中的任意希望区室。然而,为实现特定区室中的定位,例如,可以将编码区与DNA序列连接以确保在特定区室的定位。这种序列对于本领域技术人员来说是已知的(参见,例如,Braun等,EMBO J.11(1992),3219-3227;Wolter等,Proc.Natl.Acad.Sci.USA 85(1988),846-850;Sonnewald等,植物杂志(Plant J.)1(1991),95-106)。
使用已知技术可使转基因植物细胞再生成整个植物。原则上转基因植物可以是任意种类的所需植物,即,可以是单子叶和双子叶植物。
以这种方式通过同源(=天然)基因或基因序列的超量表达,抑制或阻止或异源(=外源)基因或基因序列的表达,可以获得具有改进特性的转基因植物。
根据本发明的化合物可优选用在转基因作物,其可耐受包括磺酰基脲、草铵膦-铵或草甘膦-异丙铵及类似活性化合物的除草剂。
当根据本发明的活性化合物用在转基因的作物时,除了对抗可在其他作物时观察到的有害植物的效应外,经常还包括对于相应的转基因作物特异性的效应,例如改良或特别广效地控制杂草,可供使用的改变的使用量,优选与转基因的作物可耐受的除草剂有良好的组合性,以及对转基因的作物的生长及收成产生影响。
本发明因此也提供根据本发明的化合物作为除草剂用于转基因的作物中控制有害的植物的用途。
而且,根据本发明的物质对作物可展现杰出的生长调节性质,它们以调节的方式参与植物本身的代谢,因此可供专注于植物成份控制及供促进收获使用,例如通过刺激干燥及生长抑制。而且它们也适于供一般地控制及抑制不需要的植物生长,同时不会对植物造成伤害。植物成长的抑制在大量单子叶及双子叶作物中占有很重要的角色,因为其可降低或完全预防倒伏。
根据本发明的化合物可以惯用的配制物形式使用,例如可湿性的粉末、可乳化的浓缩物、可喷洒的溶液、喷粉剂或颗粒,因此本发明也提供含式(I)化合物的除草剂及植物生长调节剂组合物。
式(I)化合物可用许多不同方式配制,这取决于给定的生物及/或化学-物理参数,合适的配制选择实例为:可湿性的粉末(WP)、水溶性粉末(SP)、水溶性浓缩物、可乳化的浓缩物(EC)、乳液(EW)如水包油及油包水乳液、可喷洒的溶液、悬浮浓缩物(SC)、主要是油或水的分散液、可和油混合的溶液、胶囊悬浮液(CS)、喷粉剂(DP)、拌种剂、供撒施及土壤应用的颗粒、微细颗粒形式的颗粒、喷洒式颗粒、涂覆的颗粒及吸附的颗粒(GR)、可分散于水的颗粒(WG)、可溶于水的颗粒(SG)、ULV配制物、微胶囊及蜡。
原则上各个这些配制物都为已知且经揭示,例如在:Winnacker-Kuecheler,“Chemische Technologie″[化学工艺],第7册,C.HauserVerlag Munich,第4版,1986,Wade van Valkenburg,″PesticideFormulations″,Marcel Dekker,纽约,1973;K.MaRfens,″Spray Drying″Handbook,第3版,1979,G.Goodwin Ltd.伦敦。
所需要的配制助剂如惰性物质、表面活性剂、溶剂及其他添加剂也已知且经揭示,例如在:Watkins,″Handbook of Insecticide DustDiluents and Carriers″,第2版,Darland Books,Caldwell纽约,H.v.Olphen,″Introduction to Clay Colloid Chemistry″;第2版,J.Wiley & Sons,纽约;C.Marsden,″Solvents Guide″;第2版,Interscience,纽约,1963;McCutcheon’s″Detergents and Emulsifiers Annual″,MCPubl.Corp.,Ridgewood N.J.;Sisley and Wood,″Encyclopedia ofSurface Active Agents″,Chem.Publ.Co.Inc.,纽约1964;Schoenfeldt,″Grenzflaechenaktive Aethylenoxidaddukte″,Wiss.Verlagsgesell.,StuttgaRf 1976;Winnacker-Kuechler,″Chemische Technologie″,第7册,C.Hauser Verlag Munich,第4版1986。
以这些配制物为基础,也可制备含其他农药活性物质的组合物,例如杀虫剂、杀螨剂、除草剂及杀真菌剂,以及安全剂、肥料及/或生长调节剂,例如即可使用或桶混的形式。
制备可湿性的粉末,其能均匀地分散于水中,其除了活性物质外,还包含离子性及/或非离子性表面活性剂(润湿剂、分散剂),例如聚乙氧基化烷基酚类、聚乙氧基化脂肪醇类、聚乙氧化脂肪胺类、脂肪醇聚乙二醇醚硫酸酯、烷基磺酸盐、烷基苯磺酸盐、木质磺酸钠、2,2’-二萘甲烷-6,6’-二磺酸钠、二丁基萘磺酸钠或油酰甲基牛磺酸钠及稀释剂或惰性物质。制备可湿性的粉末时,需将除草性活性物质磨成细粉,例如在惯用的设备如锤磨机、鼓风磨机及喷气磨机中,并且同时或随后与配制助剂混合。
制备可乳化的浓缩物是将活性物质溶于有机溶剂中如丁醇、环己酮、二甲基甲酰胺、二甲苯或其他较高沸点的芳族化合物或烃或有机溶剂的混合物,此外还加入一或多种离子性及(或)非离子性表面活性剂(乳化剂)。可用的乳化剂的实例为:烷芳基磺酸钙例如十二烷基苯磺酸钙、或非离子性乳化剂如脂肪酸聚乙二醇酯类、烷芳基聚乙二醇醚类、脂肪醇聚乙二醇醚类、环氧丙烷/环氧乙烷缩合产物、烷基聚醚类、脱水山梨糖醇酯类如脱水山梨糖醇脂肪酸酯类或聚氧乙烯脱水山梨糖醇酯类如聚氧乙烯脱水山梨糖醇脂肪酸酯类。
喷粉剂的制得是通过磨碎活性物质及微细分布的固体物质如滑石、天然粘土如高岭土、膨润土或叶蜡石、或硅藻土而达成。
悬浮浓缩物可主要是含油或水,它们的制备可用如商业化供应的珠研磨机进行湿研磨,必要时可加入上述已经提到的表面活性剂,例如在其他配制方式的情形下所用者。
乳液例如水包油乳液(EW)的制备可通过如搅拌器、胶体研磨机及(或)静态混合器使用含水有机溶剂,必要时可加入上述已经提到的表面活性剂,例如在其他配制方式的情形下所用者。
颗粒的制备可将活性物质喷洒于吸附性、颗粒化的惰性物质上,或通过粘合剂如聚乙烯醇、聚丙烯酸钠或其他矿物油将活性物质浓缩物施加于载体的表面上例如沙、高岭土或颗粒化的惰性物质,合适的活性物质也可根据惯用于制备肥料颗粒的方法将其颗粒化,必要时可为肥料混合物的形式。
可分散于水的颗粒通常是根据惯用的方式制备,例如喷雾干燥法、流化床粒化法、圆盘粒化法、使用高速搅拌器的混合法、及没有固体惰性物质的挤出法。
对于圆盘、流化床、挤压机及喷雾制颗粒、实例方法见“Spray-DryingHandbook”第三版,1979,G.Goodwin Ltd.,London;J.E.Browning,″Agglomeration″,Chemical and Engineering 1967,pages 147 ff;″Perry’s Chemical Engineer’s Handbook″,第5版,McGraw-Hill,NewYork 1973,pp.8-57。
配制植物保护产品的更详细说明,见例如G.C.Klingman,″WeedControl as a Science″,John Wiley and Sons Inc.,New York,1961,81-96页及J.D.Freyer,S.A.Evans,″Weed Control Handbook″,第5版,Blackwell Scientific Publications,Oxford,1968,101-103页。
该农业化学配制物通常含0.1至99重量%,尤其是0.1至95重量%的式I活性物质,在可湿性粉末中,活性物质浓度为例如约10至90重量%,100重量%中剩下者包含惯用的配制成份,在可乳化的浓缩物的情形下,活性物质浓度可为约1至90重量%,5至80重量%较佳。喷粉剂形式的配制物含1至30重量%的活性物质,在大多情形下5至20重量%较佳。可喷洒的溶液约含0.05至80重量%的活性物质,2至50重量%较佳。在可分散于水的颗粒的情形下,活性物质的含量部分决定于该活性物质是固体还是液体形式及使用何种粒化辅助剂、填料等。在可分散于水的颗粒的情形下,活性物质的含量为例如1至95重量%,10至80%重量%较佳。
此外上述活性物质配制物必要时可包含于各情形下惯用的粘着剂、润湿剂、分散剂、乳化剂、渗透剂、防腐剂、抗冻剂、溶剂、填充剂、载体、着色剂、抗泡沫剂、蒸发抑制剂、pH及粘度调节剂。
可与根据本发明的活性物质组合使用(为混合好的制剂或者是在桶混形式)组合配对为,如:在“杂草研究”(Weed Research)26,441-445(1986)”或者是“农药手册”,第11版,英国作物保护委员会及皇家化学协会,1997及其中所载的文献中所说明的已知活性物质。可由上述文献得知且可与根据本发明的式I化合物合并使用的已知除草剂的实例列于下文(注意:下列化合物或者为根据国际标准组织(ISO)的通用名,或者为化学名,有的则带有常用的编号):
乙草胺;三氟羧草醚;苯草醚;AKH 7088,即[[[1-[5-[2-氯-4-(三氟甲基)苯氧基]2-硝基苯基]-2-甲氧基亚乙基]氨基]氧基]乙酸及其甲基酯;甲草胺;禾草灭;莠灭净;酰嘧磺隆;杀草强;AMS,即氨基磺酸铵盐;莎稗磷;磺草灵;莠去津;azimsulfuron(DPX-A8947);aziprotryn;barban;BAS 516H,即5-氟-2-苯基-4H-3,1-苯并噁嗪-4-酮;草除灵;乙丁氟灵;呋草黄;苄嘧黄隆;地散磷;灭草松;吡草酮;benzofluor;新燕灵;苯噻隆;双丙氨酰膦,bifenox,除草定;溴丁酰草胺;溴酚肟;溴苯腈;bromuron;丁环草磷;羟草酮;丁草胺;抑草灵;丁烯草胺;buthidazole;双丁乐灵;butylate;cafenstrole(CH-900);苄草胺;磺草酮(ICI-A0051);CDAA,即2-氯-N,N-二-2-丙烯基乙酰胺;CDEC,即二乙基二硫代氨基甲酸2-氯烯丙基酯;甲氧除草醚;灭草平;炔乐灵,chlormesulan(ICI-A0051);绿秀隆;稗蓼灵;伐草克;正形素;杀草敏;氯嘧黄隆;草枯醚;绿麦隆;枯草隆;氯苯胺灵;绿黄隆;氯酞酸;草克乐;环庚草醚;醚黄隆;炔草酸及其酯,例如炔草酸炔丙酯;异噁草酮;稗草胺;cloproxydim;二氯吡啶酸;cumyluron(JC 940);氰草津;灭草特;环丙嘧磺隆(AC 104);噻草酮;环莠隆;氰氟草酯及其酯衍生物(例如丁酯,DEH-112);牧草快;环丙津;三环赛草胺;daimuron;2,4-滴丁酸;茅草枯;甜菜安;敌草净;燕麦敌;麦草畏;敌草腈;2,4-滴丙酸;禾草灵和它的酯例如禾草灵甲酯;乙酰甲草胺;枯莠隆;双苯唑快;丁噁隆;二甲草胺;二甲丙乙净;二甲酚甲胺(SAN-582H);dimethazone,异噁草酮;噻节因;dimetrasulfuron,氨基乙氟灵;地乐酚,特乐酚;双苯酰草胺;异丙净;敌草快;氟硫草定,敌草隆;二硝酚;甘草津;EL77,即5-氰基-1-(1,1-二甲基乙基)-N-甲基-1H-吡唑-4-甲酰胺;茵多杀;扑草灭;禾草畏;乙丁烯氟灵;胺苯磺隆;赛黄隆;乙嗪草酮;乙呋草黄;F5231,即N-[2-氯-4-氟-5-[4-(3-氟丙基)-4,5-二氢-5-氧代-1H-四唑-1-基]-苯基]乙磺酰胺;ethoxyfen及其酯(例如乙酯,HN-252);乙氧苯草胺(HW 52);2,4,5-涕丙酸;fenoxan,噁唑禾草灵和高噁唑禾草灵及其酯,例如高噁唑禾草灵乙酯和噁唑禾草灵乙酯;fenoxydim;非草隆;麦草伏甲酯;啶嘧黄隆;吡氟禾草灵和精吡氟禾草灵及其酯;例如吡氟禾草灵丁酯及精吡氟禾草灵丁酯;氯乙氟灵;唑嘧磺草胺;伏草隆;氟烯草酸及其酯(例如戊酯,S-23031);丙炔氟草胺(S-482);flumipropyn;胺草唑(KNW-739);三氟硝草醚;乙羧氟草醚乙酯;flupropacil(UBIC-4243);fluridone;氟咯草酮;氟草烟,呋草酮,氟黄胺草醚;蔓草磷;氟呋草醚;草铵膦;草甘膦;halosafen;氯吡嘧磺隆及其酯,例如甲酯,NC-319);吡氟氯禾灵及其酯;精吡氟氯禾灵(=R-haloxyfop)及其酯;环嗪酮;咪草酯;灭草烟;灭草喹及盐如铵盐;imazethamethapyr;咪草烟;唑吡嘧磺隆;碘苯腈;丁脒胺;异丙乐灵;异丙隆;异噁隆;异噁草胺;噁草醚;隆草特;乳氟禾草灵;环草定;利谷隆;2甲4氯;2甲4氯丁酸;2甲4氯丙酸;苯噻草胺;伏草胺;苯嗪草酮;吡草胺;甲基苯噻隆;威百亩;灭杀唑;甲氧苯酮;甲基杀草隆;metabenzuron;吡喃隆;秀谷隆;异丙甲草胺;磺草唑胺(XRD 511);甲氧隆;嗪草酮;甲黄隆;抑芽丹;草达灭;庚草利;monocarbamidedihydrogensulfate;绿谷隆;灭草隆;MT 128,即6-氯-N-(3-氯-2-丙烯基)-5-甲基-N-苯基-3-哒嗪胺;MT 5950,即,N-[3-氯4(1-甲基乙基)苯基]-2-甲基戊酰胺;萘丙胺;萘氧丙草胺;萘草胺;NC 310,即4-(2,4-二氯苯甲酰基)-1-甲基-5-苄氧基吡唑;草不隆;烟嘧黄隆;吡氯草胺;磺乐灵;除草醚;nitrofluorfen;哒草伏;坪草丹;安磺灵;oxadiargyl(RP-020630);噁草酮;乙氧氟草醚;百草枯;克草猛;二甲戊乐灵;黄草伏;棉胺宁;甜菜宁;毒莠定;哌草磷;piributicarb;pirifenop-butyl;丙草胺;氟嘧黄隆甲酯;环丙青津;氨基丙氟灵;环丙氟灵;甘扑津;扑灭通;扑草净;毒草胺;敌稗;喔草酯及其酯;扑灭津;苯胺灵;异丙草胺;戊炔草胺;prosulfalin;苄草丹;氟磺隆(CGA-152005);丙炔草胺;pyrazolinate;杀草敏;吡嘧黄隆;苄草唑;哒草特;pyrithiobac(KIH-2031);pyroxofop及其酯(例如炔丙酯);二氯喹啉酸;喹草酸;quinofop及其酯衍生物、喹禾灵及精喹禾灵及其酯,例如喹禾灵乙酯;精喹禾糖酯及乙酯;renriduron;砜嘧磺隆(DPX-E 9636);S275,即,2-[4-氯-2-氟-5-(2-丙炔基氧基)苯基]-4,5,6,7-四氢-2H-吲唑;仲丁通;稀禾定;环草隆;西玛津;西草净;SN 106279,即2-[[7-[2-氯-4-(三氟甲基)苯氧基]-2-萘基]氧基]丙酸及其甲基酯;甲磺草胺(FMC-97285,F-6285);sulfazuron;嘧黄隆;草甘膦(ICI-A0224);三氯醋酸;牧草胺(GCP-5544);特丁噻草隆;特草定;特草克;特丁草胺;特丁通;特丁津;特丁净;TFH 450,即,N,N-二乙基-3-[(2-乙基-6-甲基苯基)磺酰基]-1H-1,2,4-三唑-1-甲酰胺;噻吩草胺(NSK-850);thiazopyr(Mon-13200);thidiazimin(SN-24085);thifensulfuron-methyl;噻氟隆;杀草丹;仲草丹;肟草酮;野燕畏(阿畏达);醚苯黄隆;triazofenamide;苯黄隆;绿草定;灭草环;草达津;氟乐灵;氟胺磺隆及其酯;(例如甲酯,DPX-66037);三甲异脲;tsitodef;灭草猛;WL 110547,即5-苯氧基-1-[3-(三氟甲基)苯基]-1H-四唑;UBH-509;D-489;LS 82-556;KPP-300;NC-324;NC-330;KH-218;DPX-N8189;SC-0774;DOWCO-535;DK-8910;V-53482;PP-600;MBH-001;KIH-9201;ET-751;KIH-6127和KIH-2023。
使用时,商业化供应形式的配制物必要时可依照惯用的方法将其稀释,例如在可湿性的粉末、可乳化的浓缩剂、分散液及水分散性的颗粒的情形下用水稀释,供土壤应用或撒播的喷粉剂或颗粒形式的产物及可喷雾的溶液,使用前通常不需要以惰性物质进一步将其稀释。
式(I)化合物所需的使用量随着外界情形而变化例如温度、湿度及所用除草剂的本性,其可在很大的范围内变化,例如介于0.001至10.0公斤/公顷或更多的活性物质,但优选为介于0.005至5公斤/公顷。
A.化学实施例
1.制备4-{[3-氯-5-(三氟甲基)-2-吡啶基]氧基}-5,8-二甲基-6-[(2,6-二氧代环己基)羰基]-1,2,3,4-四氢-1λ6-硫色烯-1,1-二酮
步骤1:3-[(2,5-二甲基苯基)硫基]丙酸
将90克(2.25摩尔)的氢氧化钠溶解在500毫升水中,在10℃冷却下加入147.59克的2,5-二甲基硫酚,持续冷却并在低于25℃下加入180.1克(1.18摩尔)的3-溴丙酸,将混合物在室温下再搅拌4小时,然后用乙醚(3×500毫升)清洗,用1摩尔浓度HCl将水溶液酸化,过滤沉淀的产物并用水清洗。
产量:205.88克(92%理论值)
无色晶体,熔点:97-98℃ Rf=0.56(硅胶/醋酸乙酯)1H NMR(CDCl3):δ2.3(s,3H),2.34(s,3H),2.68(t,2H),3.1(t,2H),6.9(d,1H),7.06-7.14(2H)
步骤2:5,8-二甲基-4-二氢苯并噻喃酮
在-10℃下,将100克(0.48摩尔)的3-[(2,5-二甲基苯基)硫基]丙酸溶解在2200毫升浓硫酸中,将反应溶液在室温下搅拌1小时,然后倒入碎冰中,将水溶液用乙醚/己烷混合物(1∶9)(6×500毫升)萃取,合并的有机层经由MgSO4干燥,用旋转蒸发器完全浓缩。
产量:56.63克(62%理论值)
黄色油:Rf=0.63(硅胶/醋酸乙酯)
1H NMR(CDCl3):δ2.3(s,3H),2.6(s,3H),2.97(m,2H),3.2(m,2H),6.9-7.1(2H)
步骤3:6-溴-5,8-二甲基-4-二氢苯并噻喃酮
将66.5克(0.35摩尔)的5,8-二甲基-4-二氢苯并噻喃酮及118克(0.87摩尔)的氯化铝一起溶解或悬浮在600毫升二氯甲烷中,搅拌15分钟后,缓慢逐滴加入62.2克(0.39摩尔)的溴,随后将反应混合物在回流下沸腾10分钟,将仍温热的反应混合物倒入在碎冰中的220毫升浓盐酸中,将混合物搅拌10分钟,将二氯甲烷层分离并用乙醚(3×300毫升)萃取水层,合并的有机层用水清洗,经由MgSO4干并用旋转蒸发器浓缩。
产量:58.4克(62%理论值)
棕色晶体,熔点:87-88℃(经层析纯化后)
Rf=0.78(硅胶/醋酸乙酯)
1H NMR(CDCl3):δ2.3(s,3H),2.6(s,3H),3.0(m,2H),3.2(m,2H),7.45(2H)
步骤4:6-溴-5,8-二甲基螺[硫色满-4,2’-[1,3]二氧戊环]
将58.4克(0.22摩尔)的6-溴-5,8-二甲基-4-二氢苯并噻喃酮溶解在380毫升原甲酸三甲酯中,掺混555克(8.9摩尔)的乙二醇及0.2克的对甲苯磺酸单水合物并在80℃下搅拌过夜,随后使混合物冷却,用500毫升乙醚稀释,并用1摩尔浓度氢氧化钠水溶液及饱和的NaCl溶液的1∶1混合物(2×500毫升)及随后用饱和的NaCl溶液(300毫升)清洗,将有机层经由MgSO4干燥并用旋转蒸发器浓缩,将残留物溶解在50毫升庚烷/乙醚(9∶1)并存在放在冷处,吸滤过夜沉淀的晶体,用冷的庚烷清洗并干燥。
产量:46.38克(68%理论值)
棕色晶体:熔点:97℃;Rf=0.75(硅胶/醋酸乙酯)
1H NMR(CDCl3):δ2.2(s,3H),2.3(m,2H),2.4(s,3H),3.0(m,2H),4.15(m,2H),4.3(m,2H),7.3(s,1H)
步骤5:5,8-二甲基-4-氧代-6-硫色满羧酸
将46.38克(0.15摩尔)的6-溴-5,8-二甲基螺[硫色满-4,2’-[1,3]二氧戊环]溶解在500毫升四氢呋喃中并冷却至-65℃,随后缓慢逐滴加入80毫升(0.2摩尔)的2.5摩尔浓度在己烷中的正丁基锂,使温度不超过-55℃,将混合物再搅拌1小时,在每次少量下加入90克的干冰,随后使溶液温热至室温,加入500毫升的己烷并吸滤沉淀物,将沉淀物溶解在500毫升水中并用浓盐酸使其成为强酸性,将混合物在回流下沸腾1小时后使之冷却,吸滤沉淀的产物。
产量:26.18克(75%理论值)
无色晶体,熔点:146-198℃
1H NMR(Me2SO-d6):δ2.2(s,3H),2.5(s,3H),2.9(m,2H),3.3(m,2H),7.6(s,1H)
步骤6:5,8-二甲基-4-氧代-6-硫色满羧酸甲酯
将26.17克(0.11摩尔)的5,8-二甲基-4-氧代-6-硫色满羧酸溶解在500毫升甲醇中,掺混3毫升的浓硫酸并在回流下沸腾,在规律间隔下,另加入总量为每次3毫升的浓硫酸,直到3天后经由薄层层析(SiO2,醋酸乙酯)不再检测到起始物质,使混合物冷却,用旋转蒸发器去除甲醇,将残留物溶解在400毫升醋酸乙酯中,用饱和的NaCl溶液(2×100毫升)及饱和的NaHCO3溶液(2×100毫升)清洗混合物,经由MgSO4干燥并用旋转蒸发器浓缩。
产量:24.96克(90%理论值)
棕色油:Rf=0.7(硅胶/醋酸乙酯)
1H NMR(CDCl3):δ2.2(s,3H),2.6(s,3H),3.0(m,2H),3.2(m,2H),3.85(s,3H),7.6(s,1H)
步骤7:5,8-二甲基-4-羟基-6-硫色满羧酸甲酯
将10.40克(0.04摩尔)的5,8-二甲基-4-氧代-6-硫色满羧酸甲酯溶解在200毫升乙醇中,分批掺混0.89克(0.023摩尔)的硼氢化钠,随后将混合物在室温下再搅拌1小时,然后用旋转蒸发器浓缩,将残留物溶解在200毫升醋酸乙酯中,用饱和的NaCl溶液(2×100毫升)清洗,经由MgSO4干燥并用旋转蒸发器浓缩。
产量:10.3克(98%理论值)
棕色油,Rf=0.6(硅胶/醋酸乙酯)
1H NMR(CDCl3):δ1,8(m,1H),2.2(s,3H),2.5(m,1H),2.6(s,3H),2.8(s,1H),3.3(m,1H),3.85(s,3H),5.1(s,br,1H),7.6(s,1H)
步骤8:5,8-二甲基-4-羟基-1,1-二氧代-1,2,3,4-四氢-1λ6-硫色烯-6-羧酸甲酯
将10克(0.04摩尔)的5,8-二甲基-4-羟基-6-硫色满羧酸甲酯及4.9克(0.06摩尔)的醋酸钠一起加入200毫升甲醇中,将混合物冷却至0℃并缓慢掺混41.4克(0.07摩尔)的OXONE_(过氧单硫酸钾)在200毫升水中的溶液,在添加期间将反应温度保持低于6℃,随后将混合物在室温下搅拌4小时,然后用120毫升的水稀释,用二氯甲烷(3×200毫升)萃取混合物,将萃取液经由MgSO4干燥并用旋转蒸发器浓缩。
产量:10.6克(94%理论值)
无色晶体:熔点135-136℃;Rf=0.55(硅胶/醋酸乙酯)
1H NMR(CDCl3):δ2.5(m,2H),2.6(s,3H),2.7(s,3H),3.2(s,1H),3.9(m,1H),3.9(s,3H),5.1(m,1H),7.55(s,1H)
步骤9:4-{[3-氯-5-(三氟甲基)-2-吡啶基]氧基}-5,8-二甲基-1,1-二氧代-1,2,3,4-四氢-1λ6-硫色烯-6-羧酸甲酯
将0.48克(1.7毫摩尔)的5,8-二甲基-4-羟基-1,1-二氧代-1,2,3,4-四氢-1λ6-硫色烯-6-羧酸甲酯及0.4克(1.9毫摩尔)的2,5-二氯-3-(三氟甲基)-吡啶溶解在20毫升四氢呋喃中,随后掺混0.21克(1.9毫摩尔)的叔丁醇钾,将混合物搅拌3小时且随后用旋转蒸发器浓缩,将残留物溶解在100亳升醋酸乙酯中,用饱和的NaCl溶液(2×20毫升)清洗,经由MgSO4干燥并用旋转蒸发器浓缩,经由层析法(硅胶,醋酸乙酯∶庚烷=1∶3)纯化残留物。
产量:0.64克(80%理论值)
黄色晶体:Rf=0.71(硅胶/醋酸乙酯)
1H NMR(CDCl3):δ2.35(s,3H),2.8(m,2H),2.8(s,3H),3.25(s,1H),3.8(m,1H),3.9(s,3H),6.6(m,1H),7.7(s,1H),7.95(m,1H),8.4(m,1H)
步骤10:4-{[3-氯-5-(三氟甲基)-2-吡啶基]氧基}-5.8-二甲基-1,1-二氧代-1,2,3,4-四氢-1λ6-硫色烯-6-羧酸
将0.62克(1.3毫摩尔)的5,8-二甲基-4-羟基-1,1-二氧代-1,2,3,4-四氢-1λ6-硫色烯-6-羧酸甲酯溶解在10毫升四氢呋喃中,随后掺混在5毫升水中的0.17克(4毫摩尔)氢氧化钠,将混合物在回流下沸腾3小时,随后用旋转蒸发器将四氢呋喃去除,用5摩尔浓度HCl使残留物成为酸性,随后用醋酸乙酯萃取混合物,将萃取液经由MgSO4干燥并用旋转蒸发器浓缩。
产量:0.56克(93%理论值)
无色晶体:Rf=0.25(硅胶/醋酸乙酯)
1H NMR(CDCl3):δ2.35(s,3H),2.8(m,2H),2.8(s,3H),3.25(s,1H),3.8(m,1H),6.6(m,1H),7.9(s,1H),7.95(m,1H),8.4(m,1H)
步骤11:4-{[3-氯-5-(三氟甲基)-2-吡啶基]氧基}-5,8-二甲基-1,1-二氧代-1,2,3,4-四氢-1λ6-硫色烯-6-羧酸-3-氧代-1-环己烯酯
将在30毫升二氯甲烷中的0.56克(1.2毫摩尔)的4-{[3-氯-5-(三氟甲基)-2-吡啶基]氧基}-5,8-二甲基-1,1-二氧代-1,2,3,4-四氢-1λ6-硫色烯-6-羧酸掺混2滴的N,N-二甲基甲酰胺及0.48克(3.8毫摩尔)的草酰氯,将混合物在回流下沸腾3.5小时,随后用旋转蒸发器将溶剂去除,将残留物溶解在100毫升的二氯甲烷中,在0℃下掺混0.15克(1.4毫摩尔)的环己二酮及0.22克(3.7毫摩尔)的三乙胺,将混合物在室温下搅拌4小时,随后用旋转蒸发器浓缩,经由层析法(硅胶,醋酸乙酯:己烷=1∶1)纯化残留物。
产量:0.39克(58%理论值)
无色晶体:Rf=0.69(硅胶/醋酸乙酯)
1H NMR(CDCl3):δ2.1(m,2H),2.4(s,3H),2.45(m,2H),2.65(m,2H),2.8(m,2H),2.8(s,3H),3.25(s,1H),3.8(m,1H),6.0(s,1H),6.7(m,1H),7.85(s,1H),7.95(m,1H),8.4(m,1H)
步骤12:4-{[3-氯-5-(三氟甲基)-2-吡啶基]氧基}-5,8-二甲基-6-[(2,6-二氧代环己基)羰基]-1,2,3,4-四氢-1λ6-硫色烯-1,1-二酮
将0.31克(0.57毫摩尔)的4-{[3-氯-5-(三氟甲基)-2-吡啶基]氧基}-5,8-二甲基-1,1-二氧代-1,2,3,4-四氢-1λ6-硫色烯-6-羧酸-3-氧代-1-环己烯酯、1滴的丙酮合氰化氢及0.1克(1毫摩尔)的三乙胺溶解在15毫升的乙腈中,将混合物在室温下搅拌过液,随后用旋转蒸发器将混合物浓缩,将残留物掺混5毫升的水并用5摩尔浓度的HCl酸化,吸滤沉淀的产物并干燥。
产量:0.27克(87%理论值)
无色晶体:熔点:128-132℃;Rf=0.37(硅胶/醋酸乙酯)
1H NMR(CDCl3):δ2.0(m,2H),2.0(s,3H),2.4(m,2H),2.8(m,2H),2.8(m,2H),2.8(s,3H),3.25(s,1H),3.8(m,1H),6.6(m,1H),7.0(s,1H),7.9(m,1H),8.4(m,1H)
2.制备6-[(2,6-二氧代环己基)羰基]-5,8-二甲基-4-(2-嘧啶氧基)-1,2,3,4-四氢-1λ6-硫色烯-1,1-二酮
将0.38克(0.86毫摩尔)的5,8-二甲基-4-(2-嘧啶氧基)-1,1-二氧代-1,2,3,4-四氢-1λ6-硫色烯-6-羧酸-3-氧代-1-环己烯酯、1滴的丙酮合氰化氢及0.1克(1毫摩尔)的三乙胺溶解在15毫升的乙腈中,将混合物在室温下搅拌过液,随后用旋转蒸发器将混合物浓缩,将残留物掺混5毫升的水并且用5摩尔浓度的HCl酸化,吸滤沉淀的产物并干燥。
产量:0.28克(74%理论值)
米黄色晶体:熔点:96-99℃;Rf=0.1(硅胶/醋酸乙酯)
1H NMR(CDCl3):δ2.0(m,2H),2.05(s,3H),2.55(m,4H),2.75(s,3H),2.8(m,2H),3.2(m,1H),3.9(m,1H),6.4(m,1H),7.0(s,1H),7.05(t,2H),8.6(d,2H)
3.制备6-[(2,6-二氧代环己基)羰基]-4-苯甲酰氧基-5,8-二甲基-1,2,3,4-四氢-1λ6-硫色烯-1,1-二酮
步骤1:4-苯甲酰氧基-5,8-二甲基-1,1-二氧代-1,2,3,4-四氢-1λ6-硫色烯-6-羧酸
将1.0克(4.1毫摩尔)的5,8-二甲基-4-羟基-1,1-二氧代-1,2,3,4-四氢-1λ6-硫色烯-6-羧酸、0.58克(4.1毫摩尔)的苯甲酰氯及一刮勺尖的N,N-4-二甲氨基吡啶在10毫升吡啶中搅拌过液,随后将混合物倒入在碎冰中的5摩尔浓度HCl中并用醋酸乙酯萃取,将有机层用1摩尔浓度HCl(2×20毫升)及饱和的NaCl溶液(2×40毫升)清洗,经由MgSO4干燥并用旋转蒸发器浓缩。
产量:0.81克(52%理论值)
无色晶体:Rf=0.1(硅胶/醋酸乙酯)
1H NMR(CDCl3):δ2.4(s,3H),2.7(m,2H),2.8(s,3H),3.2(s,1H),3.9(m,1H),6.4(s,1H),7.4(m,2H),7.6(m,1H),7.8(s,1H),8.0(m,2H)
步骤2:4-苯甲酰氧基-5,8-二甲基-1,1-二氧代-1,2,3,4-四氢-1λ6-硫色烯-6-羧酸-3-氧代-1-环己烯酯
将在30毫升二氯甲烷中的0.80克(2.1毫摩尔)的4-苯甲酰氧基-5,8-二甲基-1,1-二氧代-1,2,3,4-四氢-1λ6-硫色烯-6-羧酸掺混2滴的N,N-二甲基甲酰胺及1.69克(13.3毫摩尔)的草酰氯,使混合物在回流下沸腾3.5小时,随后用旋转蒸发器将溶剂去除,将残留物溶解在100亳升的二氯甲烷中,在0℃下掺混0.25克(2.2毫摩尔)的环己二酮及0.44克(7.4毫摩尔)的三乙胺,将混合物在室温下搅拌4小时,随后用旋转蒸发器浓缩,经由层析法(硅胶,醋酸乙酯∶己烷=1∶1)纯化残留物。
产量:0.37克(25%理论值)
无色晶体:Rf=0.7(硅胶/醋酸乙酯)
1H NMR(CDCl3):δ2.1(m,2H),2.4(s,3H),2.45(m,2H),2.65(m,2H),2.8(m,2H),2.8(s,3H),3.35(s,1H),3.8(m,1H),6.0(s,1H),6.2(m,1H),7.45(m,2H),7.6(m,1H),7.8(s,1H),8.0(m,2H)
步骤3:6-[(2,6-二氧代环己基)羰基]-4-苯甲酰氧基-5,8-二甲基-1,2,3,4-四氢-1λ6-硫色烯-1,1-二酮
将0.37克(0.79毫摩尔)的4-苯甲酰氧基-5,8-二甲基-1,1-二氧代-1,2,3,4-四氢-1λ6-硫色烯-6-羧酸-3-氧代-1-环己烯酯、1滴的丙酮合氰化氢及0.14克(1.4毫摩尔)的三乙胺溶解在15毫升的乙腈中,将混合物在室温下搅拌过夜,随后用旋转蒸发器将混合物浓缩,将残留物掺混5毫升的水并用5摩尔浓度的HCl酸化,吸滤沉淀的产物并干燥。
产量:0.27克(73%理论值)
无色晶体:Rf=0.1(硅胶/醋酸乙酯)
1H NMR(CDCl3):δ2.0(m,2H),2.05(s,3H),2.4(m,4H),2.8(s,3H),2.8(m,2H),3.3(s,1H),3.9(m,1H),6.4(m,1H),7.0(s,1H),7.4(m,2H),7.6(m,1H),8.0(m,2H)
下表列出的实例是经由上述的方法制备,或可得自类似于上述的方法。
在下表中的缩写其意义如下:
Bz=苯甲酰基 Me=甲基 Et=乙基
Ph=苯基 Pr=丙基 c=环
i=异 d=二重峰 m=多重峰
q=五重峰 s=单峰 m.p.=熔点
Rt=保留时间
表1:其中取代基及下标定义如下的式(1)化合物:
A=SO2 B=CH2-CH2 R3=H
R4=H R6=OH Q=式(II)的基
Y=CH2 Z=CH2 w=0
v=1
表1a:表1化合物的前体
表1b:表1a化合物的前体
表1c:表1b化合物的前体
表2:其中取代基及下标定义如下的式(I)化合物:
A=SO2 B=CH2-CH2 E=键
R1=CH3 R2=CH3 R3=H
R7=RA,RB (X)I=O Y=CH2
Z=CH2 v =1 Q=式(II)
No. | RA | RB | Rc | RD | RE |
14 | H | H | Bz | H | H |
15 | H | Me | Bz | H | H |
16 | Me | Me | Bz | H | H |
17 | H | H | PhC(O)CH2 | H | H |
18 | H | Me | PhC(O)CH2 | H | H |
19 | Me | Me | PhC(O)CH2 | H | H |
20 | H | H | 4-Me-PhC(O) | H | H |
21 | H | Me | 4-Me-PhC(O) | H | H |
22 | Me | Me | 4-Me-PhC(O) | H | H |
23 | H | H | MeSO2 | H | H |
24 | H | Me | MeSO2 | H | H |
25 | Me | Me | MeSO2 | H | H |
26 | H | H | EtSO2 | H | H |
27 | H | Me | EtSO2 | H | H |
28 | Me | Me | EtSO2 | H | H |
29 | H | H | PrSO2 | H | H |
No. | RA | RB | Rc | RD | RE |
30 | H | Me | PrSO2 | H | H |
31 | Me | Me | PrSO2 | H | H |
32 | H | H | PhSO2 | H | H |
33 | H | Me | PhSO2 | H | H |
34 | Me | Me | PhSO2 | H | H |
35 | H | H | 4-Me-PhSO2 | H | H |
36 | H | Me | 4-Me-PhSO2 | H | H |
37 | Me | Me | 4-Me-PhSO2 | H | H |
38 | H | H | Bz | H | NO2 |
39 | H | Me | Bz | H | NO2 |
40 | Me | Me | Bz | H | NO2 |
41 | H | H | PhC(O)CH2 | H | NO2 |
42 | H | Me | PhC(O)CH2 | H | NO2 |
43 | Me | Me | PhC(O)CH2 | H | NO2 |
44 | H | H | 4-Me-PhC(O) | H | NO2 |
45 | H | Me | 4-Me-PhC(O) | H | NO2 |
46 | Me | Me | 4-Me-PhC(O) | H | NO2 |
47 | H | H | MeSO2 | H | NO2 |
48 | H | Me | MeSO2 | H | NO2 |
49 | Me | Me | MeSO2 | H | NO2 |
5O | H | H | EtSO2 | H | NO2 |
51 | H | Me | EtSO2 | H | NO2 |
52 | Me | Me | EtSO2 | H | NO2 |
53 | H | H | PrSO2 | H | NO2 |
54 | H | Me | PrSO2 | H | NO2 |
55 | Me | Me | PrSO2 | H | NO2 |
56 | H | H | PhSO2 | H | NO2 |
57 | H | Me | PhSO2 | H | NO2 |
58 | Me | Me | PhSO2 | H | NO2 |
59 | H | H | 4-Me-PhSO2 | H | NO2 |
60 | H | Me | 4-Me-PhSO2 | H | NO2 |
61 | Me | Me | 4-Me-PhSO2 | H | NO2 |
62 | H | H | Bz | H | CN |
63 | H | Me | Rz | H | CN |
64 | Me | Me | Bz | H | CN |
65 | H | H | PhC(O)CH2 | H | CN |
No. | RA | RB | Rc | RD | RE |
66 | H | Me | PhC(O)CH2 | H | CN |
67 | Me | Me | PhC(O)CH2 | H | CN |
68 | H | H | 4-Me-PhC(O) | H | CN |
69 | H | Me | 4-Me-PhC(O) | H | CN |
70 | Me | Me | 4-Me-PhC(O) | H | CN |
71 | H | H | MeSO2 | H | CN |
72 | H | Me | MeSO2 | H | CN |
73 | Me | Me | MeSO2 | H | CN |
74 | H | H | EtSO2 | H | CN |
75 | H | Me | EtSO2 | H | CN |
76 | Me | Me | EtSO2 | H | CN |
77 | H | H | PrSO2 | H | CN |
78 | H | Me | PrSO2 | H | CN |
79 | Me | Me | PrSO2 | H | CN |
80 | H | H | PhSO2 | H | CN |
81 | H | Me | PhSO2 | H | CN |
82 | Me | Me | PhSO2 | H | CN |
83 | H | H | 4-Me-PhSO2 | H | CN |
84 | H | Me | 4-Me-PhSO2 | H | CN |
85 | Me | Me | 4-Me-PhSO2 | H | CN |
86 | H | H | Bz | Cl | H |
87 | H | Me | Bz | Cl | H |
88 | Me | Me | Bz | Cl | H |
89 | H | H | PhC(O)CH2 | Cl | H |
90 | H | Me | PhC(O)CH2 | Cl | H |
91 | Me | Me | PhC(O)CH2 | Cl | H |
92 | H | H | 4-Me-PhC(O) | Cl | H |
93 | H | Me | 4-Me-PhC(O) | Cl | H |
94 | Me | Me | 4-Me-PhC(O) | Cl | H |
95 | H | H | MeSO2 | Cl | H |
96 | H | Me | MeSO2 | Cl | H |
97 | Me | Me | MeSO2 | Cl | H |
98 | H | H | EtSO2 | Cl | H |
99 | H | Me | EtSO2 | Cl | H |
100 | Me | Me | EtSO2 | Cl | H |
101 | H | H | PrSO2 | Cl | H |
No. | RA | RB | Rc | RD | RE |
102 | H | Me | PrSO2 | Cl | H |
103 | Me | Me | PrSO2 | Cl | H |
104 | H | H | PhSO2 | Cl | H |
105 | H | Me | PhSO2 | Cl | H |
106 | Me | Me | PhSO2 | Cl | H |
107 | H | H | 4-Me-PhSO2 | Cl | H |
108 | H | Me | 4-Me-PhSO2 | Cl | H |
109 | Me | Me | 4-Me-PhSO2 | Cl | H |
110 | H | H | Bz | Cl | CF3 |
111 | H | Me | Bz | Cl | CF3 |
112 | Me | Me | Bz | Cl | CF3 |
113 | H | H | PhC(O)CH2 | Cl | CF3 |
114 | H | Me | PhC(O)CH2 | Cl | CF3 |
115 | Me | Me | PhC(O)CH2 | Cl | CF3 |
116 | H | H | 4-Me-PhC(O) | Cl | CF3 |
117 | H | Me | 4-Me-PhC(O) | Cl | CF3 |
118 | Me | Me | 4-Me-PhC(O) | Cl | CF3 |
119 | H | H | MeSO2 | Cl | CF3 |
120 | H | Me | MeSO2 | Cl | CF3 |
121 | Me | Me | MeSO2 | Cl | CF3 |
122 | H | H | EtSO2 | Cl | CF3 |
123 | H | Me | EtSO2 | Cl | CF3 |
124 | Me | Me | EtSO2 | Cl | CF3 |
125 | H | H | PrSO2 | Cl | CF3 |
126 | H | Me | PrSO2 | Cl | CF3 |
127 | Me | Me | PrSO2 | Cl | CF3 |
128 | H | H | PhSO2 | Cl | CF3 |
129 | H | Me | PhSO2 | Cl | CF3 |
130 | Me | Me | PhSO2 | Cl | CF3 |
131 | H | H | 4-Me-PhSO2 | Cl | CF3 |
132 | H | Me | 4-Me-PhSO2 | Cl | CF3 |
133 | Me | Me | 4-Me-PhSO2 | Cl | CF3 |
134 | H | H | Bz | H | CF3 |
135 | H | Me | Bz | H | CF3 |
136 | Me | Me | Bz | H | CF3 |
137 | H | H | PhC(O)CH2 | H | CF3 |
No. | RA | RB | Rc | RD | RE |
138 | H | Me | PhC(O)CH2 | H | CF3 |
139 | Me | Me | PhC(O)CH2 | H | CF3 |
140 | H | H | 4-Me-PhC(O) | H | CF3 |
141 | H | Me | 4-Me-PhC(O) | H | CF3 |
142 | Me | Me | 4-Me-PhC(O) | H | CF3 |
143 | H | H | MeSO2 | H | CF3 |
144 | H | Me | MeSO2 | H | CF3 |
145 | Me | Me | MeSO2 | H | CF3 |
146 | H | H | EtSO2 | H | CF3 |
147 | H | Me | EtSO2 | H | CF3 |
148 | Me | Me | EtSO2 | H | CF3 |
149 | H | H | PrSO2 | H | CF3 |
150 | H | Me | PrSO2 | H | CF3 |
151 | Me | Me | PrSO2 | H | CF3 |
152 | H | H | PhSO2 | H | CF3 |
153 | H | Me | PhSO2 | H | CF3 |
154 | Me | Me | PhSO2 | H | CF3 |
155 | H | H | 4-Me-PhSO2 | H | CF3 |
156 | H | Me | 4-Me-PhSO2 | H | CF3 |
157 | Me | Me | 4-Me-PhSO2 | H | CF3 |
表3:其中取代基及下标定义如下的式(I)化合物:
A=SO2 B=CH2-CH2 R1=CH3
Q=式(III),其中G1-G2为NR10COR11
No. | R8 | R10 | R11 | RD | RE |
158 | H | Et | Bz | H | H |
159 | Me | Me | Bz | H | H |
160 | H | Et | 4-Me-PhC(O) | H | H |
161 | Me | Me | 4-Me-PhC(O) | H | H |
162 | H | Et | MeSO2 | H | H |
163 | Me | Me | MeSO2 | H | H |
164 | H | Et | EtSO2 | H | H |
165 | Me | Me | EtSO2 | H | H |
166 | H | Et | PrSO2 | H | H |
167 | Me | Me | PrSO2 | H | H |
168 | H | Et | PhSO2 | H | H |
169 | Me | Me | PhSO2 | H | H |
170 | H | Et | 4-Me-PhSO2 | H | H |
171 | Me | Me | 4-Me-PhSO2 | H | H |
172 | H | Et | Bz | H | NO2 |
173 | Me | Me | Bz | H | NO2 |
174 | H | Et | 4-Me-PhC(O) | H | NO2 |
175 | Me | Me | 4-Me-PhC(O) | H | NO2 |
176 | H | Et | MeSO2 | H | NO2 |
No. | R8 | R10 | R11 | RD | RE |
177 | Me | Me | MeSO2 | H | NO2 |
178 | H | Et | EtSO2 | H | NO2 |
179 | Me | Me | EtSO2 | H | NO2 |
180 | H | Et | PrSO2 | H | NO2 |
181 | Me | Me | PrSO2 | H | NO2 |
182 | H | Et | PhSO2 | H | NO2 |
183 | Me | Me | PhSO2 | H | NO2 |
184 | H | Et | 4-Me-PhSO2 | H | NO2 |
185 | Me | Me | 4-Me-PhSO2 | H | NO2 |
186 | H | Et | Bz | H | CN |
187 | Me | Me | Bz | H | CN |
188 | H | Et | 4-Me-PhC(O) | H | CN |
189 | Me | Me | 4-Me-PhC(O) | H | CN |
190 | H | Et | MeSO2 | H | CN |
191 | Me | Me | MeSO2 | H | CN |
192 | H | Et | EtSO2 | H | CN |
193 | Me | Me | EtSO2 | H | CN |
194 | H | Et | PrSO2 | H | CN |
195 | Me | Me | PrSO2 | H | CN |
196 | H | Et | PhSO2 | H | CN |
197 | Me | Me | PhSO2 | H | CN |
198 | H | Et | 4-Me-PhSO2 | H | CN |
199 | Me | Me | 4-Me-PhSO2 | H | CN |
200 | H | Et | Bz | Cl | H |
201 | Me | Me | Bz | Cl | H |
202 | H | Et | 4-Me-PhC(O) | Cl | H |
203 | Me | Me | 4-Me-PhC(O) | Cl | H |
204 | H | Et | MeSO2 | Cl | H |
205 | Me | Me | MeSO2 | Cl | H |
206 | H | Et | EtSO2 | Cl | H |
207 | Me | Me | EtSO2 | Cl | H |
208 | H | Et | PrSO2 | Cl | H |
209 | Me | Me | PrSO2 | Cl | H |
210 | H | Et | PhSO2 | Cl | H |
211 | Me | Me | PhSO2 | Cl | H |
212 | H | Et | 4-Me-PhSO2 | Cl | H |
No. | R8 | R10 | R11 | RD | RE |
213 | Me | Me | 4-Me-PhSO2 | Cl | H |
214 | H | Et | Bz | Cl | CF3 |
215 | Me | Me | Bz | Cl | CF3 |
216 | H | Et | 4-Me-PhC(O) | Cl | CF3 |
217 | Me | Me | 4-Me-PhC(O) | Cl | CF3 |
218 | H | Et | MeSO2 | Cl | CF3 |
219 | Me | Me | MeSO2 | Cl | CF3 |
220 | H | Et | EtSO2 | Cl | CF3 |
221 | Me | Me | EtSO2 | Cl | CF3 |
222 | H | Et | PrSO2 | Cl | CF3 |
223 | Me | Me | PrSO2 | Cl | CF3 |
224 | H | Et | PhSO2 | Cl | CF3 |
225 | Me | Me | PhSO2 | Cl | CF3 |
226 | H | Et | 4-Me-PhSO2 | Cl | CF3 |
227 | Me | Me | 4-Me-PhSO2 | Cl | CF3 |
228 | H | Et | Bz | H | CF3 |
229 | Me | Me | Bz | H | CF3 |
230 | H | Et | 4-Me-PhC(O) | H | CF3 |
231 | Me | Me | 4-Me-PhC(O) | H | CF3 |
232 | H | Et | MeSO2 | H | CF3 |
233 | Me | Me | MeSO2 | H | CF3 |
234 | H | Et | EtSO2 | H | CF3 |
235 | Me | Me | EtSO2 | H | CF3 |
236 | H | Et | PrSO2 | H | CF3 |
237 | Me | Me | PrSO2 | H | CF3 |
238 | H | Et | PhSO2 | H | CF3 |
239 | Me | Me | PhSO2 | H | CF3 |
240 | H | Et | 4-Me-PhSO2 | H | CF3 |
241 | Me | Me | 4-Me-PhSO2 | H | CF3 |
表4:其中取代基及下标定义如下的式(I)化合物:
A=SO2 B=CH2-CH2 R3=H
E=键 Q=式(III),其中G1-G2为OCR9
R9=c-Pr
No. | R1 | R2 | RD | RE |
242 | H | H | H | H |
243 | Me | H | H | H |
244 | Me | Me | H | H |
245 | Cl | H | H | H |
246 | Cl | Me | H | H |
247 | Cl | Cl | H | H |
248 | Me | Cl | H | H |
249 | H | H | H | NO2 |
250 | Me | H | H | NO2 |
251 | Me | Me | H | NO2 |
252 | Cl | H | H | NO2 |
253 | Cl | Me | H | NO2 |
254 | Cl | Cl | H | NO2 |
255 | Me | Cl | H | NO2 |
256 | H | H | H | CN |
257 | Me | H | H | CN |
258 | Me | Me | H | CN |
No. | R1 | R2 | RD | RE |
259 | Cl | H | H | CN |
260 | Cl | Me | H | CN |
261 | Cl | Cl | H | CN |
262 | Me | Cl | H | CN |
263 | H | H | Cl | H |
264 | Me | H | Cl | H |
265 | Me | Me | Cl | H |
266 | Cl | H | Cl | H |
267 | Cl | Me | Cl | H |
268 | Cl | Cl | Cl | H |
269 | Me | Cl | Cl | H |
270 | H | H | Cl | CF3 |
271 | Me | H | Cl | CF3 |
272 | Me | Me | Cl | CF3 |
273 | Cl | H | Cl | CF3 |
274 | Cl | Me | Cl | CF3 |
275 | Cl | Cl | Cl | CF3 |
276 | Me | Cl | Cl | CF3 |
277 | H | H | H | CF3 |
278 | Me | H | H | CF3 |
279 | Me | Me | H | CF3 |
280 | Cl | H | H | CF3 |
281 | Cl | Me | H | CF3 |
282 | Cl | Cl | H | CF3 |
283 | Me | Cl | H | CF3 |
表5:其中取代基及下标定义如下的式(I)化合物:
A=SO2 B=CH2-CH2 R3=H
E=键 Q=式(III)其中G1-G2为SCR9
R9=c-Pr
No. | R1 | R2 | RD | RE |
284 | H | H | H | H |
285 | Me | H | H | H |
286 | Me | Me | H | H |
287 | Cl | H | H | H |
288 | Cl | Me | H | H |
289 | Cl | Cl | H | H |
290 | Me | Cl | H | H |
291 | H | H | H | NO2 |
292 | Me | H | H | NO2 |
293 | Me | Me | H | NO2 |
294 | Cl | H | H | NO2 |
295 | Cl | Me | H | NO2 |
296 | Cl | Cl | H | NO2 |
297 | Me | Cl | H | NO2 |
298 | H | H | H | CN |
299 | Me | H | H | CN |
300 | Me | Me | H | CN |
301 | Cl | H | H | CN |
No. | R1 | R2 | RD | RE |
302 | Cl | Me | H | CN |
303 | Cl | Cl | H | CN |
304 | Me | Cl | H | CN |
305 | H | H | Cl | H |
306 | Me | H | Cl | H |
307 | Me | Me | Cl | H |
308 | Cl | H | Cl | H |
309 | Cl | Me | Cl | H |
310 | Cl | Cl | Cl | H |
311 | Me | Cl | Cl | H |
312 | H | H | Cl | CF3 |
313 | Me | H | Cl | CF3 |
314 | Me | Me | Cl | CF3 |
315 | Cl | H | Cl | CF3 |
316 | Cl | Me | Cl | CF3 |
317 | Cl | Cl | Cl | CF3 |
318 | Me | Cl | Cl | CF3 |
319 | H | H | H | CF3 |
320 | Me | H | H | CF3 |
321 | Me | Me | H | CF3 |
322 | Cl | H | H | CF3 |
323 | Cl | Me | H | CF3 |
324 | Cl | Cl | H | CF3 |
325 | Me | Cl | H | CF3 |
表6:其中取代基及下标定义如下的式(I)化合物:
A=SO2 B=CH2-CH2 R3=H
R4=H
(X)I=O
E=键 Q=式(IV) R9=c-Pr
No. | R1 | R2 | RD | RE |
326 | H | H | H | H |
327 | Me | H | H | H |
328 | Me | Me | H | H |
329 | Cl | H | H | H |
330 | Cl | Me | H | H |
331 | Cl | Cl | H | H |
332 | Me | Cl | H | H |
333 | H | H | H | NO2 |
334 | Me | H | H | NO2 |
335 | Me | Me | H | NO2 |
336 | Cl | H | H | NO2 |
337 | Cl | Me | H | NO2 |
338 | Cl | Cl | H | NO2 |
339 | Me | Cl | H | NO2 |
340 | H | H | H | CN |
341 | Me | H | H | CN |
342 | Me | Me | H | CN |
343 | Cl | H | H | CN |
No. | R1 | R2 | RD | RE |
344 | Cl | Me | H | CN |
345 | Cl | Cl | H | CN |
346 | Me | Cl | H | CN |
347 | H | H | Cl | H |
348 | Me | H | Cl | H |
349 | Me | Me | Cl | H |
350 | Cl | H | Cl | H |
351 | Cl | Me | Cl | H |
352 | Cl | Cl | Cl | H |
353 | Me | Cl | Cl | H |
354 | H | H | Cl | CF3 |
355 | Me | H | Cl | CF3 |
356 | Me | Me | Cl | CF3 |
357 | Cl | H | Cl | CF3 |
358 | Cl | Me | Cl | CF3 |
359 | Cl | Cl | Cl | CF3 |
360 | Me | Cl | Cl | CF3 |
361 | H | H | H | CF3 |
362 | Me | H | H | CF3 |
363 | Me | Me | H | CF3 |
364 | Cl | H | H | CF3 |
365 | Cl | Me | H | CF3 |
366 | Cl | Cl | H | CF3 |
367 | Me | Cl | H | CF3 |
表7:其中取代基及下标定义如下的式(I)化合物:
A=SO2 E=键 R1=Me
R2=Me R3=H R4=H
R7=RA,RB (X)I=O Y=CH2
Z=CH2 V=1
No. | RA | RB | R1 | R2 | B | RD | RE |
368 | H | H | H | H | CH2CH2 | H | H |
369 | Me | H | H | H | CH2CH2 | H | H |
370 | Me | Me | H | H | CH2CH2 | H | H |
371 | H | H | Me | H | CH2CH2 | H | H |
372 | Me | H | Me | H | CH2CH2 | H | H |
373 | Me | Me | Me | H | CH2CH2 | H | H |
374 | H | H | Cl | H | CH2CH2 | H | H |
375 | Me | H | Cl | H | CH2CH2 | H | H |
376 | Me | Me | Cl | H | CH2CH2 | H | H |
377 | H | H | H | Me | CH2CH2 | H | H |
378 | Me | H | H | Me | CH2CH2 | H | H |
379 | Me | Me | H | Me | CH2CH2 | H | H |
380 | H | H | Me | Me | CH2CH2 | H | H |
381 | Me | H | Me | Me | CH2CH2 | H | H |
382 | Me | Me | Me | Me | CH2CH2 | H | H |
383 | H | H | Me | Cl | CH2CH2 | H | H |
384 | Me | H | Me | Cl | CH2CH2 | H | H |
No. | RA | RB | R1 | R2 | B | RD | RE |
385 | Me | Me | Me | Cl | CH2CH2 | H | H |
386 | H | H | Cl | Me | CH2CH2 | H | H |
387 | Me | H | Cl | Me | CH2CH2 | H | H |
388 | Me | Me | Cl | Me | CH2CH2 | H | H |
389 | H | H | H | Cl | CH2CH2 | H | H |
390 | Me | H | H | Cl | CH2CH2 | H | H |
391 | Me | Me | H | Cl | CH2CH2 | H | H |
392 | H | H | Cl | Cl | CH2CH2 | H | H |
393 | Me | H | Cl | Cl | CH2CH2 | H | H |
394 | Me | Me | Cl | Cl | CH2CH2 | H | H |
395 | H | H | H | H | CH2CH2 | H | NO2 |
396 | Me | H | H | H | CH2CH2 | H | NO2 |
397 | Me | Me | H | H | CH2CH2 | H | NO2 |
398 | H | H | Me | H | CH2CH2 | H | NO2 |
399 | Me | H | Me | H | CH2CH2 | H | NO2 |
400 | Me | Me | Me | H | CH2CH2 | H | NO2 |
401 | H | H | Cl | H | CH2CH2 | H | NO2 |
402 | Me | H | Cl | H | CH2CH2 | H | NO2 |
403 | Me | Me | Cl | H | CH2CH2 | H | NO2 |
404 | H | H | H | Me | CH2CH2 | H | NO2 |
405 | Me | H | H | Me | CH2CH2 | H | NO2 |
406 | Me | Me | H | Me | CH2CH2 | H | NO2 |
407 | H | H | Me | Me | CH2CH2 | H | NO2 |
408 | Me | H | Me | Me | CH2CH2 | H | NO2 |
409 | Me | Me | Me | Me | CH2CH2 | H | NO2 |
410 | H | H | Me | Cl | CH2CH2 | H | NO2 |
411 | Me | H | Me | Cl | CH2CH2 | H | NO2 |
412 | Me | Me | Me | Cl | CH2CH2 | H | NO2 |
413 | H | H | Cl | Me | CH2CH2 | H | NO2 |
414 | Me | H | Cl | Me | CH2CH2 | H | NO2 |
415 | Me | Me | Cl | Me | CH2CH2 | H | NO2 |
416 | H | H | H | Cl | CH2CH2 | H | NO2 |
417 | Me | H | H | Cl | CH2CH2 | H | NO2 |
418 | Me | Me | H | Cl | CH2CH2 | H | NO2 |
419 | H | H | Cl | Cl | CH2CH2 | H | NO2 |
420 | Me | H | Cl | Cl | CH2CH2 | H | NO2 |
No. | RA | RB | R1 | R2 | B | RD | RE |
421 | Me | Me | Cl | Cl | CH2CH2 | H | NO2 |
422 | H | H | H | H | CH2CH2 | H | CN |
423 | Me | H | H | H | CH2CH2 | H | CN |
424 | Me | Me | H | H | CH2CH2 | H | CN |
425 | H | H | Me | H | CH2CH2 | H | CN |
426 | Me | H | Me | H | CH2CH2 | H | CN |
427 | Me | Me | Me | H | CH2CH2 | H | CN |
428 | H | H | Cl | H | CH2CH2 | H | CN |
429 | Me | H | Cl | H | CH2CH2 | H | CN |
430 | Me | Me | Cl | H | CH2CH2 | H | CN |
431 | H | H | H | Me | CH2CH2 | H | CN |
432 | Me | H | H | Me | CH2CH2 | H | CN |
433 | Me | Me | H | Me | CH2CH2 | H | CN |
434 | H | H | Me | Me | CH2CH2 | H | CN |
435 | Me | H | Me | Me | CH2CH2 | H | CN |
436 | Me | Me | Me | Me | CH2CH2 | H | CN |
437 | H | H | Me | Cl | CH2CH2 | H | CN |
438 | Me | H | Me | Cl | CH2CH2 | H | CN |
439 | Me | Me | Me | Cl | CH2CH2 | H | CN |
440 | H | H | Cl | Me | CH2CH2 | H | CN |
441 | Me | H | Cl | Me | CH2CH2 | H | CN |
442 | Me | Me | Cl | Me | CH2CH2 | H | CN |
443 | H | H | H | Cl | CH2CH2 | H | CN |
444 | Me | H | H | Cl | CH2CH2 | H | CN |
445 | Me | Me | H | Cl | CH2CH2 | H | CN |
446 | H | H | Cl | Cl | CH2CH2 | H | CN |
447 | Me | H | Cl | Cl | CH2CH2 | H | CN |
448 | Me | Me | Cl | Cl | CH2CH2 | H | CN |
449 | H | H | H | H | CH2CH2 | Cl | H |
450 | Me | H | H | H | CH2CH2 | Cl | H |
451 | Me | Me | H | H | CH2CH2 | Cl | H |
452 | H | H | Me | H | CH2CH2 | Cl | H |
453 | Me | H | Me | H | CH2CH2 | Cl | H |
454 | Me | Me | Me | H | CH2CH2 | Cl | H |
455 | H | H | Cl | H | CH2CH2 | Cl | H |
456 | Me | H | Cl | H | CH2CH2 | Cl | H |
No. | RA | RB | R1 | R2 | B | RD | RE |
457 | Me | Me | Cl | H | CH2CH2 | Cl | H |
458 | H | H | H | Me | CH2CH2 | Cl | H |
459 | Me | H | H | Me | CH2CH2 | Cl | H |
460 | Me | Me | H | Me | CH2CH2 | Cl | H |
461 | H | H | Me | Me | CH2CH2 | Cl | H |
462 | Me | H | Me | Me | CH2CH2 | Cl | H |
463 | Me | Me | Me | Me | CH2CH2 | Cl | H |
464 | H | H | Me | Cl | CH2CH2 | Cl | H |
465 | Me | H | Me | Cl | CH2CH2 | Cl | H |
466 | Me | Me | Me | Cl | CH2CH2 | Cl | H |
467 | H | H | Cl | Me | CH2CH2 | Cl | H |
468 | Me | H | Cl | Me | CH2CH2 | Cl | H |
469 | Me | Me | Cl | Me | CH2CH2 | Cl | H |
470 | H | H | H | Cl | CH2CH2 | Cl | H |
471 | Me | H | H | Cl | CH2CH2 | Cl | H |
472 | Me | Me | H | Cl | CH2CH2 | Cl | H |
473 | H | H | Cl | Cl | CH2CH2 | Cl | H |
474 | Me | H | Cl | Cl | CH2CH2 | Cl | H |
475 | Me | Me | Cl | Cl | CH2CH2 | Cl | H |
476 | H | H | H | H | CH2CH2 | Cl | CF3 |
477 | Me | H | H | H | CH2CH2 | Cl | CF3 |
478 | Me | Me | H | H | CH2CH2 | Cl | CF3 |
479 | H | H | Me | H | CH2CH2 | Cl | CF3 |
480 | Me | H | Me | H | CH2CH2 | Cl | CF3 |
481 | Me | Me | Me | H | CH2CH2 | Cl | CF3 |
482 | H | H | Cl | H | CH2CH2 | Cl | CF3 |
483 | Me | H | Cl | H | CH2CH2 | Cl | CF3 |
484 | Me | Me | Cl | H | CH2CH2 | Cl | CF3 |
485 | H | H | H | Me | CH2CH2 | Cl | CF3 |
486 | Me | H | H | Me | CH2CH2 | Cl | CF3 |
487 | Me | Me | H | Me | CH2CH2 | Cl | CF3 |
488 | H | H | Me | Me | CH2CH2 | Cl | CF3 |
489 | Me | H | Me | Me | CH2CH2 | Cl | CF3 |
490 | Me | Me | Me | Me | CH2CH2 | Cl | CF3 |
491 | H | H | Me | Cl | CH2CH2 | Cl | CF3 |
492 | Me | H | Me | Cl | CH2CH2 | Cl | CF3 |
No. | RA | RB | R1 | R2 | B | RD | RE |
493 | Me | Me | Me | Cl | CH2CH2 | Cl | CF3 |
494 | H | H | Cl | Me | CH2CH2 | Cl | CF3 |
495 | Me | H | Cl | Me | CH2CH2 | Cl | CF3 |
496 | Me | Me | Cl | Me | CH2CH2 | Cl | CF3 |
497 | H | H | H | Cl | CH2CH2 | Cl | CF3 |
498 | Me | H | H | Cl | CH2CH2 | Cl | CF3 |
499 | Me | Me | H | Cl | CH2CH2 | Cl | CF3 |
500 | H | H | Cl | Cl | CH2CH2 | Cl | CF3 |
501 | Me | H | Cl | Cl | CH2CH2 | Cl | CF3 |
502 | Me | Me | Cl | Cl | CH2CH2 | Cl | CF3 |
503 | H | H | H | H | CH2CH2 | H | CF3 |
504 | Me | H | H | H | CH2CH2 | H | CF3 |
505 | Me | Me | H | H | CH2CH2 | H | CF3 |
506 | H | H | Me | H | CH2CH2 | H | CF3 |
507 | Me | H | Me | H | CH2CH2 | H | CF3 |
508 | Me | Me | Me | H | CH2CH2 | H | CF3 |
509 | H | H | Cl | H | CH2CH2 | H | CF3 |
510 | Me | H | Cl | H | CH2CH2 | H | CF3 |
511 | Me | Me | Cl | H | CH2CH2 | H | CF3 |
512 | H | H | H | Me | CH2CH2 | H | CF3 |
513 | Me | H | H | Me | CH2CH2 | H | CF3 |
514 | Me | Me | H | Me | CH2CH2 | H | CF3 |
515 | H | H | Me | Me | CH2CH2 | H | CF3 |
516 | Me | H | Me | Me | CH2CH2 | H | CF3 |
517 | Me | Me | Me | Me | CH2CH2 | H | CF3 |
518 | H | H | Me | Cl | CH2CH2 | H | CF3 |
519 | Me | H | Me | Cl | CH2CH2 | H | CF3 |
520 | Me | Me | Me | Cl | CH2CH2 | H | CF3 |
521 | H | H | Cl | Me | CH2CH2 | H | CF3 |
522 | Me | H | Cl | Me | CH2CH2 | H | CF3 |
523 | Me | Me | Cl | Me | CH2CH2 | H | CF3 |
524 | H | H | H | Cl | CH2CH2 | H | CF3 |
525 | Me | H | H | Cl | CH2CH2 | H | CF3 |
526 | Me | Me | H | Cl | CH2CH2 | H | CF3 |
527 | H | H | Cl | Cl | CH2CH2 | H | CF3 |
528 | Me | H | Cl | Cl | CH2CH2 | H | CF3 |
No. | RA | RB | R1 | R2 | B | RD | RE |
529 | Me | Me | Cl | Cl | CH2CH2 | H | CF3 |
530 | H | H | H | H | CH2CH2CH2 | H | H |
531 | Me | H | H | H | CH2CH2CH2 | H | H |
532 | Me | Me | H | H | CH2CH2CH2 | H | H |
533 | H | H | Me | H | CH2CH2CH2 | H | H |
534 | Me | H | Me | H | CH2CH2CH2 | H | H |
535 | Me | Me | Me | H | CH2CH2CH2 | H | H |
536 | H | H | Cl | H | CH2CH2CH2 | H | H |
537 | Me | H | Cl | H | CH2CH2CH2 | H | H |
538 | Me | Me | Cl | H | CH2CH2CH2 | H | H |
539 | H | H | H | Me | CH2CH2CH2 | H | H |
540 | Me | H | H | Me | CH2CH2CH2 | H | H |
541 | Me | Me | H | Me | CH2CH2CH2 | H | H |
542 | H | H | Me | Me | CH2CH2CH2 | H | H |
543 | Me | H | Me | Me | CH2CH2CH2 | H | H |
544 | Me | Me | Me | Me | CH2CH2CH2 | H | H |
545 | H | H | Me | Cl | CH2CH2CH2 | H | H |
546 | Me | H | Me | Cl | CH2CH2CH2 | H | H |
547 | Me | Me | Me | Cl | CH2CH2CH2 | H | H |
548 | H | H | Cl | Me | CH2CH2CH2 | H | H |
550 | Me | H | Cl | Me | CH2CH2CH2 | H | H |
551 | Me | Me | Cl | Me | CH2CH2CH2 | H | H |
552 | H | H | H | Cl | CH2CH2CH2 | H | H |
553 | Me | H | H | Cl | CH2CH2CH2 | H | H |
554 | Me | Me | H | Cl | CH2CH2CH2 | H | H |
555 | H | H | Cl | Cl | CH2CH2CH2 | H | H |
556 | Me | H | Cl | Cl | CH2CH2CH2 | H | H |
557 | Me | Me | Cl | Cl | CH2CH2CH2 | H | H |
558 | H | H | H | H | CH2CH2CH2 | H | NO2 |
559 | Me | H | H | H | CH2CH2CH2 | H | NO2 |
560 | Me | Me | H | H | CH2CH2CH2 | H | NO2 |
561 | H | H | Me | H | CH2CH2CH2 | H | NO2 |
562 | Me | H | Me | H | CH2CH2CH2 | H | NO2 |
563 | Me | Me | Me | H | CH2CH2CH2 | H | NO2 |
564 | H | H | Cl | H | CH2CH2CH2 | H | NO2 |
565 | Me | H | Cl | H | CH2CH2CH2 | H | NO2 |
No. | RA | RB | R1 | R2 | B | RD | RE |
566 | Me | Me | Cl | H | CH2CH2CH2 | H | NO2 |
567 | H | H | H | Me | CH2CH2CH2 | H | NO2 |
568 | Me | H | H | Me | CH2CH2CH2 | H | NO2 |
569 | Me | Me | H | Me | CH2CH2CH2 | H | NO2 |
570 | H | H | Me | Me | CH2CH2CH2 | H | NO2 |
571 | Me | H | Me | Me | CH2CH2CH2 | H | NO2 |
572 | Me | Me | Me | Me | CH2CH2CH2 | H | NO2 |
573 | H | H | Me | Cl | CH2CH2CH2 | H | NO2 |
574 | Me | H | Me | Cl | CH2CH2CH2 | H | NO2 |
575 | Me | Me | Me | Cl | CH2CH2CH2 | H | NO2 |
576 | H | H | Cl | Me | CH2CH2CH2 | H | NO2 |
577 | Me | H | Cl | Me | CH2CH2CH2 | H | NO2 |
578 | Me | Me | Cl | Me | CH2CH2CH2 | H | NO2 |
579 | H | H | H | Cl | CH2CH2CH2 | H | NO2 |
580 | Me | H | H | Cl | CH2CH2CH2 | H | NO2 |
581 | Me | Me | H | Cl | CH2CH2CH2 | H | NO2 |
582 | H | H | Cl | Cl | CH2CH2CH2 | H | NO2 |
583 | Me | H | Cl | Cl | CH2CH2CH2 | H | NO2 |
584 | Me | Me | Cl | Cl | CH2CH2CH2 | H | NO2 |
585 | H | H | H | H | CH2CH2CH2 | Cl | H |
586 | Me | H | H | H | CH2CH2CH2 | Cl | H |
587 | Me | Me | H | H | CH2CH2CH2 | Cl | H |
588 | H | H | Me | H | CH2CH2CH2 | Cl | H |
589 | Me | H | Me | H | CH2CH2CH2 | Cl | H |
590 | Me | Me | Me | H | CH2CH2CH2 | Cl | H |
591 | H | H | Cl | H | CH2CH2CH2 | Cl | H |
592 | Me | H | Cl | H | CH2CH2CH2 | Cl | H |
593 | Me | Me | Cl | H | CH2CH2CH2 | Cl | H |
594 | H | H | H | Me | CH2CH2CH2 | Cl | H |
595 | Me | H | H | Me | CH2CH2CH2 | Cl | H |
596 | Me | Me | H | Me | CH2CH2CH2 | Cl | H |
597 | H | H | Me | Me | CH2CH2CH2 | Cl | H |
598 | Me | H | Me | Me | CH2CH2CH2 | Cl | H |
599 | Me | Me | Me | Me | CH2CH2CH2 | Cl | H |
600 | H | H | Me | Cl | CH2CH2CH2 | Cl | H |
601 | Me | H | Me | Cl | CH2CH2CH2 | Cl | H |
No. | RA | RB | R1 | R2 | B | RD | RE |
602 | Me | Me | Me | Cl | CH2CH2CH2 | Cl | H |
603 | H | H | Cl | Me | CH2CH2CH2 | Cl | H |
604 | Me | H | Cl | Me | CH2CH2CH2 | Cl | H |
605 | Me | Me | Cl | Me | CH2CH2CH2 | Cl | H |
606 | H | H | H | Cl | CH2CH2CH2 | Cl | H |
607 | Me | H | H | Cl | CH2CH2CH2 | Cl | H |
608 | Me | Me | H | Cl | CH2CH2CH2 | Cl | H |
609 | H | H | Cl | Cl | CH2CH2CH2 | Cl | H |
610 | Me | H | Cl | Cl | CH2CH2CH2 | Cl | H |
611 | Me | Me | Cl | Cl | CH2CH2CH2 | Cl | H |
612 | H | H | H | H | CH2CH2CH2 | Cl | CF3 |
613 | Me | H | H | H | CH2CH2CH2 | Cl | CF3 |
614 | Me | Me | H | H | CH2CH2CH2 | Cl | CF3 |
615 | H | H | Me | H | CH2CH2CH2 | Cl | CF3 |
616 | Me | H | Me | H | CH2CH2CH2 | Cl | CF3 |
617 | Me | Me | Me | H | CH2CH2CH2 | Cl | CF3 |
618 | H | H | Cl | H | CH2CH2CH2 | Cl | CF3 |
619 | Me | H | Cl | H | CH2CH2CH2 | Cl | CF3 |
620 | Me | Me | Cl | H | CH2CH2CH2 | Cl | CF3 |
621 | H | H | H | Me | CH2CH2CH2 | Cl | CF3 |
622 | Me | H | H | Me | CH2CH2CH2 | Cl | CF3 |
623 | Me | Me | H | Me | CH2CH2CH2 | Cl | CF3 |
624 | H | H | Me | Me | CH2CH2CH2 | Cl | CF3 |
625 | Me | H | Me | Me | CH2CH2CH2 | Cl | CF3 |
626 | Me | Me | Me | Me | CH2CH2CH2 | Cl | CF3 |
627 | H | H | Me | Cl | CH2CH2CH2 | Cl | CF3 |
628 | Me | H | Me | Cl | CH2CH2CH2 | Cl | CF3 |
629 | Me | Me | Me | Cl | CH2CH2CH2 | Cl | CF3 |
630 | H | H | Cl | Me | CH2CH2CH2 | Cl | CF3 |
631 | Me | H | Cl | Me | CH2CH2CH2 | Cl | CF3 |
632 | Me | Me | Cl | Me | CH2CH2CH2 | Cl | CF3 |
633 | H | H | H | Cl | CH2CH2CH2 | Cl | CF3 |
634 | Me | H | H | Cl | CH2CH2CH2 | Cl | CF3 |
635 | Me | Me | H | Cl | CH2CH2CH2 | Cl | CF3 |
636 | H | H | Cl | Cl | CH2CH2CH2 | Cl | CF3 |
637 | Me | H | Cl | Cl | CH2CH2CH2 | Cl | CF3 |
No. | RA | RB | R1 | R2 | B | RD | RE |
638 | Me | Me | Cl | Cl | CH2CH2CH2 | Cl | CF3 |
639 | H | H | H | H | CH2CH2CH2 | H | CF3 |
640 | Me | H | H | H | CH2CH2CH2 | H | CF3 |
641 | Me | Me | H | H | CH2CH2CH2 | H | CF3 |
642 | H | H | Me | H | CH2CH2CH2 | H | CF3 |
643 | Me | H | Me | H | CH2CH2CH2 | H | CF3 |
644 | Me | Me | Me | H | CH2CH2CH2 | H | CF3 |
645 | H | H | Cl | H | CH2CH2CH2 | H | CF3 |
646 | Me | H | Cl | H | CH2CH2CH2 | H | CF3 |
647 | Me | Me | Cl | H | CH2CH2CH2 | H | CF3 |
648 | H | H | H | Me | CH2CH2CH2 | H | CF3 |
649 | Me | H | H | Me | CH2CH2CH2 | H | CF3 |
650 | Me | Me | H | Me | CH2CH2CH2 | H | CF3 |
651 | H | H | Me | Me | CH2CH2CH2 | H | CF3 |
652 | Me | H | Me | Me | CH2CH2CH2 | H | CF3 |
653 | Me | Me | Me | Me | CH2CH2CH2 | H | CF3 |
654 | H | H | Me | Cl | CH2CH2CH2 | H | CF3 |
655 | Me | H | Me | Cl | CH2CH2CH2 | H | CF3 |
656 | Me | Me | Me | Cl | CH2CH2CH2 | H | CF3 |
657 | H | H | Cl | Me | CH2CH2CH2 | H | CF3 |
658 | Me | H | Cl | Me | CH2CH2CH2 | H | CF3 |
659 | Me | Me | Cl | Me | CH2CH2CH2 | H | CF3 |
660 | H | H | H | Cl | CH2CH2CH2 | H | CF3 |
661 | Me | H | H | Cl | CH2CH2CH2 | H | CF3 |
662 | Me | Me | H | Cl | CH2CH2CH2 | H | CF3 |
663 | H | H | Cl | Cl | CH2CH2CH2 | H | CF3 |
664 | Me | H | Cl | Cl | CH2CH2CH2 | H | CF3 |
665 | Me | Me | Cl | Cl | CH2CH2CH2 | H | CF3 |
表8:其中取代基及下标定义如下的式(I)化合物:
A=SO2 B=CH2CH2 R1=Me
R2=Me R3=H Q=式(II)的基
R6=OH Y=CH2 Z=CH2
v=1 w=0
No. | (X)I | E | R4 | R5 | 物理数据 |
666 | O | 键 | H | 苯基 | |
667 | O | 键 | H | 4-硝基苯基 | |
668 | O | 键 | H | 4-氯苯基 | |
669 | O | 键 | H | 3-吡啶基 | |
670 | O | 键 | H | 5-三氟甲基-2-吡啶基 | |
671 | O | 键 | H | 2-甲基-1-吡咯基 | |
672 | O | 键 | H | 4-甲基-2-噻吩基 | |
673 | O | 键 | H | 3-甲硫基-2-吡啶基 | |
674 | O | 键 | H | 5-甲氨基羰基-2- | |
675 | O | 键 | H | 1,2,3-噻二唑-4-基 | m.p.:192-196℃ |
676 | O | 键 | H | 4,6-二甲氧基-1,3,5-三嗪-2-基 | |
677 | S | 键 | H | 苯基 | |
678 | S | 键 | H | 4-硝基苯基 |
No. | (X)I | E | R4 | R5 | 物理数据 |
679 | S | 键 | H | 4-氯苯基 | |
680 | S | 键 | H | 2-吡啶基 | m.p.:212-215℃ |
681 | S | 键 | H | 5-硝基-2-吡啶基 | |
682 | S | 键 | H | 2-嘧啶基 | m.p.:270℃ |
683 | S | 键 | H | 4,6-二甲基-2-嘧啶基 | |
684 | S | 键 | H | 4,6-二甲氧基-2-嘧啶基 | |
685 | S | 键 | H | 2-吡嗪基 | |
686 | S | 键 | H | 1,2,3-噻二唑-4-基 | |
687 | S | 键 | H | 4,6-二甲氧基-1,3,5-三嗪-2-基 | |
688 | NH | 键 | H | 苯基 | |
689 | NH | 键 | H | 4-硝基苯基 | |
690 | NH | 键 | H | 4-氯苯基 | |
691 | NH | 键 | H | 吡啶基 | |
692 | NH | 键 | H | 5-硝基-2-吡啶基 | |
693 | NH | 键 | H | 2-嘧啶基 | |
694 | NH | 键 | H | 4,6-二甲基-2-嘧啶基 | |
695 | NH | 键 | H | 4,6-二甲氧基-2-嘧啶基 | |
696 | NH | 键 | H | 2-吡嗪基 | |
697 | NH | 键 | H | 1,2,3-噻二唑-4-基 | |
698 | NH | 键 | H | 4,6-二甲氧基-1,3,5-三嗪-2-基 | |
699 | NMe | 键 | H | 苯基 | |
700 | NMe | 键 | H | 4-硝基苯基 | |
701 | NMe | 键 | H | 4-氯苯基 | |
702 | NMe | 键 | H | 吡啶基 | |
703 | NMe | 键 | H | 5-硝基-2-吡啶基 | |
704 | NMe | 键 | H | 2-嘧啶基 | |
705 | NMe | 键 | H | 4,6-二甲基-2-嘧啶基 | |
706 | NMe | 键 | H | 4,6-二甲氧基-2-嘧啶基 |
No. | (X)I | E | R4 | R5 | 物理数据 |
707 | NMe | 键 | H | 2-吡嗪基 | |
708 | NMe | 键 | H | 1,2,3-噻二唑-4-基 | |
709 | NMe | 键 | H | 4,6-二甲氧基-1,3,5-三嗪-2-基 | |
710 | NCHO | 键 | H | 苯基 | |
711 | NCHO | 键 | H | 4-硝基苯基 | |
712 | NCHO | 键 | H | 4-氯苯基 | |
713 | NCHO | 键 | H | 吡啶基 | |
714 | NCHO | 键 | H | 5-硝基-2-吡啶基 | |
715 | NCHO | 键 | H | 2-嘧啶基 | |
716 | NCHO | 键 | H | 4.6-二甲基-2-嘧啶基 | |
717 | NCHO | 键 | H | 4,6-二甲氧基-2-嘧啶基 | |
718 | NCHO | 键 | H | 2-吡嗪基 | |
719 | NCHO | 键 | H | 1,2,3-噻二唑-4-基 | |
720 | NCHO | 键 | H | 4,6-二甲氧基-1,3,5-三嗪-2-基 | |
721 | O | CH2 | H | 2-氯-4-硝基-苯基 | |
722 | O | CH2 | H | 4-硝基苯基 | |
723 | O | CH2 | H | 4-氯苯基 | |
724 | O | CH2 | H | 吡啶基 | |
725 | O | CH2 | H | 5-硝基-2-吡啶基 | |
726 | O | CH2 | H | 2-嘧啶基 | |
727 | O | CH2 | H | 4,6-二甲基-2-嘧啶基 | |
728 | O | CH2 | H | 4,6-二甲氧基-2-嘧啶基 | |
729 | O | CH2 | H | 2-吡嗪基 | |
730 | O | CH2 | H | 1,2,3-噻二唑-4-基 | |
731 | O | CH2 | H | 4,6-二甲氧基-1,3,5-三嗪-2-基 | |
732 | S | CH2 | H | 苯基 | |
733 | S | CH2 | H | 4-硝基苯基 | |
734 | S | CH2 | H | 4-氯苯基 | |
735 | S | CH2 | H | 吡啶基 | |
736 | S | CH2 | H | 5-硝基-2-吡啶基 |
No. | (X)I | E | R4 | R5 | 物理数据 |
737 | S | CH2 | H | 2-嘧啶基 | |
738 | S | CH2 | H | 4,6-二甲基-2-嘧啶基 | |
739 | S | CH2 | H | 4,6-二甲氧基-2-嘧啶基 | |
740 | S | CH2 | H | 2-吡嗪基 | |
741 | S | CH2 | H | 1,2,3-噻二唑-4-基 | |
742 | S | CH2 | H | 4,6-二甲氧基-1,3,5-三嗪-2-基 | |
743 | NH | CH2 | H | 苯基 | |
744 | NH | CH2 | H | 4-硝基苯基 | |
745 | NH | CH2 | H | 4-氯苯基 | |
746 | NH | CH2 | H | 吡啶基 | |
747 | NH | CH2 | H | 5-硝基-2-吡啶基 | |
748 | NH | CH2 | H | 2-嘧啶基 | |
749 | NH | CH2 | H | 4,6-二甲基-2-嘧啶基 | |
750 | NH | CH2 | H | 4,6-二甲氧基-2-嘧啶基 | |
751 | NH | CH2 | H | 2-吡嗪基 | |
752 | NH | CH2 | H | 1,2,3-噻二唑-4-基 | |
753 | NH | CH2 | H | 4,6-二甲氧基-1,3,5-三嗪-2-基 | |
754 | NMe | CH2 | H | 苯基 | |
755 | NMe | CH2 | H | 4-硝基苯基 | |
756 | NMe | CH2 | H | 4-氯苯基 | |
757 | NMe | CH2 | H | 吡啶基 | |
758 | NMe | CH2 | H | 5-硝基-2-吡啶基 | |
759 | NMe | CH2 | H | 2-嘧啶基 | |
760 | NMe | CH2 | H | 4,6-二甲基-2-嘧啶基 | |
761 | NMe | CH2 | H | 4,6-二甲氧基-2-嘧啶基 | |
762 | NMe | CH2 | H | 2-吡嗪基 | |
763 | NMe | CH2 | H | 1,2,3-噻二唑-4-基 | |
764 | NMe | CH2 | H | 4,6-二甲氧基-1,3,5-三嗪-2-基 | |
765 | NCHO | CH2 | H | 苯基 | |
766 | NCHO | CH2 | H | 4-硝基苯基 |
No. | (X)I | E | R4 | R5 | 物理数据 |
767 | NCHO | CH2 | H | 4-氯苯基 | |
768 | NCHO | CH2 | H | 吡啶基 | |
769 | NCHO | CH2 | H | 5-硝基-2-吡啶基 | |
770 | NCHO | CH2 | H | 2-嘧啶基 | |
771 | NCHO | CH2 | H | 4,6-二甲基-2-嘧啶基 | |
772 | NCHO | CH2 | H | 4,6-二甲氧基-2-嘧啶基 | |
773 | NCHO | CH2 | H | 2-吡嗪基 | |
774 | NCHO | CH2 | H | 1,2,3-噻二唑-4-基 | |
775 | NCHO | CH2 | H | 4,6-二甲氧基-1,3,5-三嗪-2-基 | |
776 | O | C(O) | H | 3-二氟甲氧基苯基 | |
777 | O | C(O) | H | 4-硝基苯基 | |
778 | O | C(O) | H | 4-氯苯基 | |
779 | O | C(O) | H | 吡啶基 | |
780 | O | C(O) | H | 5-硝基-2-吡啶基 | |
781 | O | C(O) | H | 2-嘧啶基 | |
782 | O | C(O) | H | 4,6-二甲基-2-嘧啶基 | |
783 | O | C(O) | H | 4,6-二甲氧基-2-嘧啶基 | |
784 | O | C(O) | H | 2-吡嗪基 | |
785 | O | C(O) | H | 1,2,3-噻二唑-4-基 | |
786 | O | C(O) | H | 4,6-二甲氧基-1,3,5-三嗪-2-基 | |
787 | S | C(O) | H | 苯基 | |
788 | S | C(O) | H | 4-硝基苯基 | |
789 | S | C(O) | H | 4-氯苯基 | |
790 | S | C(O) | H | 吡啶基 | |
791 | S | C(O) | H | 5-硝基-2-吡啶基 | |
792 | S | C(O) | H | 2-嘧啶基 | |
793 | S | C(O) | H | 4,6-二甲基-2-嘧啶基 | |
794 | S | C(O) | H | 4,6-二甲氧基-2-嘧啶基 | |
795 | S | C(O) | H | 2-吡嗪基 | |
796 | S | C(O) | H | 1,2,3-噻二唑-4-基 |
No. | (X)I | E | R4 | R5 | 物理数据 |
797 | S | C(O) | H | 4,6-二甲氧基-1,3,5-三嗪-2-基 | |
798 | NH | C(O) | H | 苯基 | |
799 | NH | C(O) | H | 4-硝基苯基 | |
800 | NH | C(O) | H | 4-氯苯基 | |
801 | NH | C(O) | H | 吡啶基 | |
802 | NH | C(O) | H | 5-硝基-2-吡啶基 | |
803 | NH | C(O) | H | 2-嘧啶基 | |
804 | NH | C(O) | H | 4,6-二甲基-2-嘧啶基 | |
805 | NH | C(O) | H | 4,6-二甲氧基-2-嘧啶基 | |
806 | NH | C(O) | H | 2-吡嗪基 | |
807 | NH | C(O) | H | 1,2,3-噻二唑-4-基 | |
808 | NH | C(O) | H | 4,6-二甲氧基-1,3,5-三嗪-2-基 | |
809 | NMe | C(O) | H | 苯基 | |
810 | NMe | C(O) | H | 4-硝基苯基 | |
811 | NMe | C(O) | H | 4-氯苯基 | |
812 | NMe | C(O) | H | 吡啶基 | |
813 | NMe | C(O) | H | 5-硝基-2-吡啶基 | |
814 | NMe | C(O) | H | 2-嘧啶基 | |
815 | NMe | C(O) | H | 4,6-二甲基-2-嘧啶基 | |
816 | NMe | C(O) | H | 4,6-二甲氧基-2-嘧啶基 | |
817 | NMe | C(O) | H | 2-吡嗪基 | |
818 | NMe | C(O) | H | 1,2,3-噻二唑-4-基 | |
819 | NMe | C(O) | H | 4,6-二甲氧基-1,3,5-三嗪-2-基 | |
820 | NCHO | C(O) | H | 苯基 | |
821 | NCHO | C(O) | H | 4-硝基苯基 | |
822 | NCHO | C(O) | H | 4-氯苯基 | |
823 | NCHO | C(O) | H | 吡啶基 | |
824 | NCHO | C(O) | H | 5-硝基-2-吡啶基 | |
825 | NCHO | C(O) | H | 2-嘧啶基 | |
826 | NCHO | C(O) | H | 4,6-二甲基-2-嘧啶基 |
No. | (X)I | E | R4 | R5 | 物理数据 |
827 | NCHO | C(O) | H | 4,6-二甲氧基-2-嘧啶基 | |
828 | NCHO | C(O) | H | 2-吡嗪基 | |
829 | NCHO | C(O) | H | 1,2,3-噻二唑-4-基 | |
830 | NCHO | C(O) | H | 4,6-二甲氧基-1,3,5-三嗪-2-基 | |
831 | O | SO2 | H | 苯基 | |
832 | O | SO2 | H | 4-硝基苯基 | |
833 | O | SO2 | H | 4-氯苯基 | |
834 | O | SO2 | H | 吡啶基 | |
835 | O | SO2 | H | 5-硝基-2-吡啶基 | |
836 | O | SO2 | H | 2-嘧啶基 | |
837 | O | SO2 | H | 4,6-二甲基-2-嘧啶基 | |
838 | O | SO2 | H | 4,6-二甲氧基-2-嘧啶基 | |
839 | O | SO2 | H | 2-吡嗪基 | |
840 | O | SO2 | H | 1,2,3-噻二唑-4-基 | |
841 | O | SO2 | H | 4,6-二甲氧基-1,3,5-三嗪-2-基 | |
842 | NH | SO2 | H | 苯基 | |
843 | NH | SO2 | H | 4-硝基苯基 | |
844 | NH | SO2 | H | 4-氯苯基 | |
845 | NH | SO2 | H | 吡啶基 | |
846 | NH | SO2 | H | 5-硝基-2-吡啶基 | |
847 | NH | SO2 | H | 2-嘧啶基 | |
848 | NH | SO2 | H | 4,6-二甲基-2-嘧啶基 | |
849 | NH | SO2 | H | 4,6-二甲氧基-2-嘧啶基 | |
850 | NH | SO2 | H | 2-吡嗪基 | |
851 | NH | SO2 | H | 1,2,3-噻二唑-4-基 | |
852 | NH | SO2 | H | 4,6-二甲氧基-1,3,5-三嗪-2-基 | |
853 | NMe | SO2 | H | 苯基 | |
854 | NMe | SO2 | H | 4-硝基苯基 | |
855 | NMe | SO2 | H | 4-氯苯基 | |
856 | NMe | SO2 | H | 吡啶基 |
No. | (X)I | E | R4 | R5 | 物理数据 |
857 | NMe | SO2 | H | 5-硝基-2-吡啶基 | |
858 | NMe | SO2 | H | 2-嘧啶基 | |
859 | NMe | SO2 | H | 4,6-二甲基-2-嘧啶基 | |
860 | NMe | SO2 | H | 4,6-二甲氧基-2-嘧啶基 | |
861 | NMe | SO2 | H | 2-吡嗪基 | |
862 | NMe | SO2 | H | 1,2,3-噻二唑-4-基 | |
863 | NMe | SO2 | H | 4,6-二甲氧基-1,3,5-三嗪-2-基 | |
864 | O | CH2 | Me | 苯基 | |
865 | O | CH2 | Me | 4-硝基苯基 | |
866 | O | CH2 | Me | 4-氯苯基 | |
867 | O | CH2 | Me | 吡啶基 | |
868 | O | CH2 | Me | 5-硝基-2-吡啶基 | |
869 | O | CH2 | Me | 2-嘧啶基 | |
870 | O | CH2 | Me | 4,6-二甲基-2-嘧啶基 | |
871 | O | CH2 | Me | 4,6-二甲氧基-2-嘧啶基 | |
872 | O | CH2 | Me | 2-吡嗪基 | |
873 | O | CH2 | Me | 1,2,3-噻二唑-4-基 | |
874 | O | CH2 | Me | 4,6-二甲氧基-1,3,5-三嗪-2-基 | |
875 | S | CH2 | Me | 苯基 | |
876 | S | CH2 | Me | 4-硝基苯基 | |
877 | S | CH2 | Me | 4-氯苯基 | |
878 | S | CH2 | Me | 吡啶基 | |
879 | S | CH2 | Me | 5-硝基-2-吡啶基 | |
880 | S | CH2 | Me | 2-嘧啶基 | |
881 | S | CH2 | Me | 4,6-二甲基-2-嘧啶基 | |
882 | S | CH2 | Me | 4,6-二甲氧基-2-嘧啶基 | |
883 | S | CH2 | Me | 2-吡嗪基 | |
884 | S | CH2 | Me | 1,2,3-噻二唑-4-基 | |
885 | S | CH2 | Me | 4,6-二甲氧基-1,3,5-三嗪-2-基 | |
886 | NH | CH2 | Me | 苯基 |
No. | (X)I | E | R4 | R5 | 物理数据 |
887 | NH | CH2 | Me | 4-硝基苯基 | |
888 | NH | CH2 | Me | 4-氯苯基 | |
889 | NH | CH2 | Me | 吡啶基 | |
890 | NH | CH2 | Me | 5-硝基-2-吡啶基 | |
891 | NH | CH2 | Me | 2-嘧啶基 | |
892 | NH | CH2 | Me | 4,6-二甲基-2-嘧啶基 | |
893 | NH | CH2 | Me | 4,6-二甲氧基-2-嘧啶基 | |
894 | NH | CH2 | Me | 2-吡嗪基 | |
895 | NH | CH2 | Me | 1,2,3-噻二唑-4-基 | |
896 | NH | CH2 | Me | 4,6-二甲氧基-1,3,5-三嗪-2-基 | |
897 | NMe | CH2 | Me | 苯基 | |
898 | NMe | CH2 | Me | 4-硝基苯基 | |
899 | NMe | CH2 | Me | 4-氯苯基 | |
900 | NMe | CH2 | Me | 吡啶基 | |
901 | NMe | CH2 | Me | 5-硝基-2-吡啶基 | |
902 | NMe | CH2 | Me | 2-嘧啶基 | |
903 | NMe | CH2 | Me | 4,6-二甲基-2-嘧啶基 | |
904 | NMe | CH2 | Me | 4,6-二甲氧基-2-嘧啶基 | |
905 | NMe | CH2 | Me | 2-吡嗪基 | |
906 | NMe | CH2 | Me | 1,2,3-噻二唑-4-基 | |
907 | NMe | CH2 | Me | 4,6-二甲氧基-1,3,5-三嗪-2-基 | |
908 | NCHO | CH2 | Me | 苯基 | |
909 | NCHO | CH2 | Me | 4-硝基苯基 | |
910 | NCHO | CH2 | Me | 4-氯苯基 | |
911 | NCHO | CH2 | Me | 吡啶基 | |
912 | NCHO | CH2 | Me | 5-硝基-2-吡啶基 | |
913 | NCHO | CH2 | Me | 2-嘧啶基 | |
914 | NCHO | CH2 | Me | 4,6-二甲基-2-嘧啶基 | |
915 | NCHO | CH2 | Me | 4,6-二甲氧基-2-嘧啶基 | |
916 | NCHO | CH2 | Me | 2-吡嗪基 |
No. | (X)I | E | R4 | R5 | 物理数据 |
917 | NCHO | CH2 | Me | 1,2,3-噻二唑-4-基 | |
918 | NCHO | CH2 | Me | 4,6-二甲氧基-1,3,5-三嗪-2-基 | |
919 | O | C(O) | Me | 苯基 | |
920 | O | C(O) | Me | 4-硝基苯基 | |
921 | O | C(O) | Me | 4-氯苯基 | |
922 | O | C(O) | Me | 吡啶基 | |
923 | O | C(O) | Me | 5-硝基-2-吡啶基 | |
924 | O | C(O) | Me | 2-嘧啶基 | |
925 | O | C(O) | Me | 4,6-二甲基-2-嘧啶基 | |
926 | O | C(O) | Me | 4,6-二甲氧基-2-嘧啶基 | |
927 | O | C(O) | Me | 2-吡嗪基 | |
928 | O | C(O) | Me | 1,2,3-噻二唑-4-基 | |
929 | O | C(O) | Me | 4,6-二甲氧基-1,3,5-三嗪-2-基 | |
930 | S | C(O) | Me | 苯基 | |
931 | S | C(O) | Me | 4-硝基苯基 | |
932 | S | C(O) | Me | 4-氯苯基 | |
933 | S | C(O) | Me | 吡啶基 | |
934 | S | C(O) | Me | 5-硝基-2-吡啶基 | |
935 | S | C(O) | Me | 2-嘧啶基 | |
936 | S | C(O) | Me | 4,6-二甲基-2-嘧啶基 | |
937 | S | C(O) | Me | 4,6-二甲氧基-2-嘧啶基 | |
938 | S | C(O) | Me | 2-吡嗪基 | |
939 | S | C(O) | Me | 1,2,3-噻二唑-4-基 | |
940 | S | C(O) | Me | 4,6-二甲氧基-1,3,5-三嗪-2-基 | |
941 | NH | C(O) | Me | 苯基 | |
942 | NH | C(O) | Me | 4-硝基苯基 | |
943 | NH | C(O) | Me | 4-氯苯基 | |
944 | NH | C(O) | Me | 吡啶基 | |
945 | NH | C(O) | Me | 5-硝基-2-吡啶基 | |
946 | NH | C(O) | Me | 2-嘧啶基 |
No. | (X)I | E | R4 | R5 | 物理数据 |
947 | NH | C(O) | Me | 4,6-二甲基-2-嘧啶基 | |
948 | NH | C(O) | Me | 4,6-二甲氧基-2-嘧啶基 | |
949 | NH | C(O) | Me | 2-吡嗪基 | |
950 | NH | C(O) | Me | 1,2,3-噻二唑-4-基 | |
951 | NH | C(O) | Me | 4,6-二甲氧基-1,3,5-三嗪-2-基 | |
952 | NMe | C(O) | Me | 苯基 | |
953 | NMe | C(O) | Me | 4-硝基苯基 | |
954 | NMe | C(O) | Me | 4-氯苯基 | |
955 | NMe | C(O) | Me | 吡啶基 | |
956 | NMe | C(O) | Me | 5-硝基-2-吡啶基 | |
957 | NMe | C(O) | Me | 2-嘧啶基 | |
958 | NMe | C(O) | Me | 4,6-二甲基-2-嘧啶基 | |
959 | NMe | C(O) | Me | 4,6-二甲氧基-2-嘧啶基 | |
960 | NMe | C(O) | Me | 2-吡嗪基 | |
961 | NMe | C(O) | Me | 1,2,3-噻二唑-4-基 | |
962 | NMe | C(O) | Me | 4,6-二甲氧基-1,3,5-三嗪-2-基 | |
963 | NCHO | C(O) | Me | 苯基 | |
964 | NCHO | C(O) | Me | 4-硝基苯基 | |
965 | NCHO | C(O) | Me | 4-氯苯基 | |
966 | NCHO | C(O) | Me | 吡啶基 | |
967 | NCHO | C(O) | Me | 5-硝基-2-吡啶基 | |
968 | NCHO | C(O) | Me | 2-嘧啶基 | |
969 | NCHO | C(O) | Me | 4,6-二甲基-2-嘧啶基 | |
970 | NCHO | C(O) | Me | 4,6-二甲氧基-2-嘧啶基 | |
971 | NCHO | C(O) | Me | 2-吡嗪基 | |
972 | NCHO | C(O) | Me | 1,2,3-噻二唑-4-基 | |
973 | NCHO | C(O) | Me | 4,6-二甲氧基-1,3,5-三嗪-2-基 |
表9:其中取代基及下标定义如下的式(I)化合物:
A=SO2 E=键 R1=Me
R2=Me R3=H R4=H
Y=CH2 Z=CH2 v=1
w=0
No. | R6 | A | B |
974 | OBz | SO2 | CH2CH2 |
975 | SH | SO2 | CH2CH2 |
976 | SPh | SO2 | CH2CH2 |
977 | Cl | SO2 | CH2CH2 |
978 | OH | SO | CH2CH2 |
979 | SH | SO | CH2CH2 |
980 | SPh | SO | CH2CH2 |
981 | Cl | SO | CH2CH2 |
982 | OH | S | CH2CH2 |
983 | SH | S | CH2CH2 |
984 | SPh | S | CH2CH2 |
985 | Cl | S | CH2CH2 |
986 | OH | CH2 | CH2CH2 |
987 | SH | CH2 | CH2CH2 |
988 | SPh | CH2 | CH2CH2 |
989 | Cl | CH2 | CH2CH2 |
990 | OH | NSO2Me | CH2CH2 |
No. | R6 | A | B |
991 | SH | NSO2Me | CH2CH2 |
992 | SPh | NSO2Me | CH2CH2 |
993 | Cl | NSO2Me | CH2CH2 |
994 | OH | O | CH2CH2 |
995 | SH | O | CH2CH2 |
996 | SPh | O | CH2CH2 |
997 | Cl | O | CH2CH2 |
998 | OH | NH | CH2CH2 |
999 | SH | NH | CH2CH2 |
1000 | SPh | NH | CH2CH2 |
1001 | Cl | NH | CH2CH2 |
1002 | OH | SO2 | CH2CH2CH2 |
1003 | SH | SO2 | CH2CH2CH2 |
1004 | SPh | SO2 | CH2CH2CH2 |
1005 | Cl | SO2 | CH2CH2CH2 |
1006 | OH | SO | CH2CH2CH2 |
1007 | SH | SO | CH2CH2CH2 |
1008 | SPh | SO | CH2CH2CH2 |
1009 | Cl | SO | CH2CH2CH2 |
1010 | OH | S | CH2CH2CH2 |
1011 | SH | S | CH2CH2CH2 |
1012 | SPh | S | CH2CH2CH2 |
1013 | Cl | S | CH2CH2CH2 |
1014 | OH | CH2 | CH2CH2CH2 |
1015 | SH | CH2 | CH2CH2CH2 |
1016 | SPh | CH2 | CH2CH2CH2 |
1017 | Cl | CH2 | CH2CH2CH2 |
1018 | OH | NSO2Me | CH2CH2CH2 |
1019 | SH | NSO2Me | CH2CH2CH2 |
1020 | SPh | NSO2Me | CH2CH2CH2 |
1021 | Cl | NSO2Me | CH2CH2CH2 |
1022 | OH | O | CH2CH2CH2 |
1023 | SH | O | CH2CH2CH2 |
1024 | SPh | O | CH2CH2CH2 |
1025 | Cl | O | CH2CH2CH2 |
1026 | OH | NH | CH2CH2CH2 |
No. | R6 | A | B |
1027 | SH | NH | CH2CH2CH2 |
1028 | SPh | NH | CH2CH2CH2 |
1029 | Cl | NH | CH2CH2CH2 |
1030 | OH | SO2 | CH=CH |
1031 | SH | SO2 | CH=CH |
1032 | SPh | SO2 | CH=CH |
1033 | Cl | SO2 | CH=CH |
1034 | OH | SO | CH=CH |
1035 | SH | SO | CH=CH |
1036 | SPh | SO | CH=CH |
1037 | Cl | SO | CH=CH |
1038 | OH | S | CH=CH |
1039 | SH | S | CH=CH |
1040 | SPh | S | CH=CH |
1041 | Cl | S | CH=CH |
1042 | OH | CH2 | CH=CH |
1043 | SH | CH2 | CH=CH |
1044 | SPh | CH2 | CH=CH |
1045 | Cl | CH2 | CH=CH |
1046 | OH | NSO2Me | CH=CH |
1047 | SH | NSO2Me | CH=CH |
1048 | SPh | NSO2Me | CH=CH |
1049 | Cl | NSO2Me | CH=CH |
1050 | OH | O | CH=CH |
1051 | SH | O | CH=CH |
1052 | SPh | O | CH=CH |
1053 | Cl | O | CH=CH |
1054 | OH | NH | CH=CH |
1055 | SH | NH | CH=CH |
1056 | SPh | NH | CH=CH |
1057 | Cl | NH | CH=CH |
表10:其中取代基及下标定义如下的式(I)化合物:
A=SO2 B=CH2-CH2 R3=H
R4=H Y=CH2 Z=CH2
R7=RA,RB,RC,RD Q=式(II)的基
I=1 v=1
No. | RA,RB | Rc,RD | R1 | R2 | X | E | R5 | 物理数据 |
1058 | H,H | H,H | H | H | S | 键 | 2-吡啶基 | 1H NMR(CDCl3):δ2.1(m,2H),2.4(m,2H),2.7(m,2H),2.8(m,1H),3.05(m,1H),3.4(m,1H),3.9(m,1H),5,62(m,1H),7.1(m,1H),7.18(d,1H),7.65(m,1H),7.7(s,1H),7,95(m,1H),8.5(m,1H) |
1059 | H,H | H,H | Me | Me | S | 键 | 2-甲基-1,3,4-噻二唑-5-基 | 1H NMR(CDCl3):δ2.05(m,2H),2.35(s,3H),2.45(m,2H),2.7(m,2H),2.75(s,3H),2.8(s,3H),2.95(m,3H),3.45(m,1H),4.15(m,1H),5.7(m,1H),6.96(s,1H) |
1060 | H,H | H,H | H | H | S | 键 | 2-嘧啶基 | m.p.133℃ |
1061 | H,H | H,H | Me | Me | O | 键 | 3-氰基-2-吡啶基 | m.p.232-238℃ |
1062 | Me,Me | H,H | Me | Me | O | 键 | 3-氰基-2-吡啶基 | m.p.141-144℃ |
1063 | H,H | H,H | Me | Me | O | 键 | 3-硝基-2-苯基 | m.p.158℃ |
No. | RA,RB | RC,RD | R1 | R2 | X | E | R5 | 物理数据 |
1064 | Me,Me | H,H | Me | Me | O | 键 | 4,6-二甲氧基-2-嘧啶基 | m.p.133-136℃ |
1065 | H,H | Me,Me | Me | Me | O | 键 | 2-嘧啶基 | 1H NMR(CDCL3)δ1.3(m,2H),1.9(m,2H),2.05(s,3H),2.38(s,3H),2.8(m,4H),3.2(m,1H),3.9(m,1H),6.45(m,1H),6.98(s,1H),7.05(m,1H),8.6(m,1H) |
1066 | H,H | H,H | Me | Me | O | 键 | Ph | 1H NMR(CDCl3):δ1.95(s,3H),2.1(m,2H),2.6(m,4H),2.7(s,3H),2.7(m,2H),3.15(m,1H),3.5(m,1H),3.65(s,2H),6.1(m,1H),6.98(s,1H),7.3(m,5H) |
1067 | H,H | H,H | Me | Me | O | 键 | 3-氟-4-硝基苯基 | m.p.236-238℃ |
表11:其中取代基及下标定义如下的式(I)化合物:
A=SO2 B=CH2-CH2 R1=CH3
R2=CH3 R3=H R4=H
R11=H Q=式(III)的基
No. | R8 | R10 | X | E | R5 | 物理数据 |
1068 | Me | Me | O | 键 | 3-硝基-6-吡啶基 | m.p.149℃ |
1069 | Me | Me | O | 键 | 3-氟-4-硝基苯基 | m.p.159℃ |
1070 | Me | Me | O | 键 | 2-硝基苯基 | m.p.165℃ |
1071 | Me | Me | S | 键 | 2-嘧啶基 | 1H NMR(CDCl3):δ1.75(s,3H),2.1(s,3H),2.8(s,3H),2.8(m,1H),2.95(m,1H),3.4(m,1H),3.65(s,3H),4.2(m,1H),5.45(m,1H),7.1(t,1H),7.25(2,1H),8.6(d,2H) |
1072 | Me | Me | O | 键 | 2-嘧啶基 | 1H NMR(CDCl3):δ1.75(s,3H),2.12(s,3H),2.8(s,3H),2.82(m,2H),3.3(m,1H),3.95(m,1H),6.45(m,1H),7.05(t,1H),7.22(s,1H),7.32(s,1H),8.6(d,2H) |
1073 | Me | Me | O | 键 | 4,6-二甲基-2-嘧啶基 | 1H NMR(CDCl3):δ1.75(s,3H),2.12(s,3H),2.45(s,6H),2.8(s,3H),2.82(m.2H),3.25(m,1H),3.98(m,1H),6.45(m,1H),6.78(s,1H),7.2(s,1H),7.45(s,1H) |
1074 | H | Et | O | 键 | 1,4-二嗪基 | 1H NMR(CDCl3):δ1.45(t,3H),2.2(s,3H),2.85(s,3H),2.85(m,2H),3.3(m,1H),3.85(m,1H),4.05(quartet,2H),6.5(m,1H),7.35(s,1H),7.4(s,1H),8.15(m,1H),8.25(m,2H) |
1075 | H | Et | O | 键 | 2-嘧啶基 | 1H NMR(CDCl3):δ1.45(t,3H),2.25(s,3H),2.82(s,3H),2.85(m,2H),3.25(m,1H),3.95(m,1H),4.05(quartet,2H),6.45(m,1H),7.05(m,1H),7.35(s,1H),7.38(s,1H),8.6(m,2H) |
表12:其中取代基及下标定义如下的式(I)化合物:
A=SO2 B=CH2-CH2 E=键
R1=CH3 R2=CH3 R3=H
R4=H R6=OH Y=CH2
Z=CH2 Q=式(II)的基 I=0
v=1 w=0
No. | R5 | 物理数据 |
1076 | 1-吡唑基 | m.p.213-218℃ |
1077 | 1,2,3-三唑-2-基 | 1H NMR(CDCl3):δ1.8(s,3H),2.05(m,2H),2.42(m,2H),2.78(m,3H),2.8(s,3H),3.08(m,1H),3.2(m,1H),3.6(m,1H),6.15(m,1H),7.02(s,1H),7.65(s,2H) |
1078 | 1,2,3-三唑-1-基 | Rt=0.05(SiO2;醋酸乙酯) |
1079 | 3-甲基-吡唑-1-基 | |
1080 | 1,2,4-三唑-1-基 | Rt=0.04(SiO2;醋酸乙酯) |
1081 | 3-三氟甲基-吡唑-1-基 | Rt=0.33(SiO2;醋酸乙酯) |
1082 | 3,5-二甲基-吡唑-1-基 | m.p.176-181℃ |
1083 | 4-甲基-吡唑-1-基 | m.p.138-142℃ |
1084 | 4-溴-吡唑-1-基 | Rt=0.26(SiO2;醋酸乙酯) |
1085 | 1-吡咯基 | |
1086 | 1-咪唑基 | |
1087 | 2-硝基-咪唑-1-基 | |
1088 | 4-硝基-咪唑-1-基 | m.p.162-172℃ |
表13:其中取代基及下标定义如下的式(I)化合物:
A=SO2 B=CH2-CH2 R1=CH3
R2=CH3 R3=H R4=H
R4=c-Pr Q=式(III)的基,其中G1-G2为OCR9
No. | I | x | E | R5 | 物理数据 |
1101 | 1 | O | 键 | 1,4-二嗪基 | 1H NMR(CDCl3):δ1.2-1.4(m,4H),2.18(s,3H),2.61(m,1H),2.81(s,3H),2.85(m,2H),3.35(m,1H),3.85(m,1H),6.52(m,1H),7.35(s,1H),8.18(m,2H),8.25(m,2H) |
1102 | 1 | O | 键 | 4,6-二甲氧基-2-嘧啶基 | 1H NMR(CDCl3):δ1.2-1.4(m,4H),2.25(s,3H),2.45(m,1H),2.8(s,3H),2.8(m,1H),2.8-3.2(m,2H),3.3(m,1H),3.95(m,1H),3.95(s,6H),6.4(m,1H),7.3(s,1H),8.2(s,1H) |
1103 | 1 | O | 键 | 2-嘧啶基 | |
1104 | 0 | 键 | 1-吡唑基 | ||
1105 | 0 | 键 | 1,2,3-三唑-2-基 |
表14:其中取代基及下标定义如下的式(I)化合物:
A=SO2 B=CH2-CH2 R1=CH3
R2=CH3 R3=H R4=H
Q=式(IV)的基 R9=c-Pr
No. | I | x | E | R5 | 物理数据 |
1106 | 1 | O | 键 | 1,4-二嗪基 | 1H NMR(CDCl3):δ1.3(m,2H),1.42(m,2H),2.22(s,3H),2.38(m,1H),2.82(m,3H),3.3(m,1H),3.8(m,1H),6.5(m,1H),7.42(s,1H),8.2(m,1H),8.25(m,2H),8.25(s,1H) |
1107 | 1 | O | 键 | 2-嘧啶基 | |
1108 | 0 | 键 | 1-吡唑基 |
表15:其中取代基及下标定义如下的式(I)化合物:
A=SO2 B=CH2-CH2 E=键
R1=CH3 R2=CH3 R3=H
R4=H R6=OH Y=CH2
Z=CH2 Q=式(II)的基 I=0
V=1 w=0
No. | I | x | E | R5 | R11 |
1109 | 1 | O | 键 | 1,4-二嗪基 | Bz |
1110 | 1 | O | 键 | 1,4-二嗪基 | 4-Me-PhC(O) |
1111 | 1 | O | 键 | 1,4-二嗪基 | MeSO2 |
1112 | 1 | O | 键 | 1,4-二嗪基 | EtSO2 |
1113 | 1 | O | 键 | 1,4-二嗪基 | PrSO2 |
1114 | 1 | O | 键 | 1,4-二嗪基 | PhSO2 |
1115 | 1 | O | 键 | 1,4-二嗪基 | 4-Me-PhSO2 |
1116 | 1 | O | 键 | 2-嘧啶基 | Bz |
1117 | 1 | O | 键 | 2-嘧啶基 | 4-Me-PhC(O) |
1118 | 1 | O | 键 | 2-嘧啶基 | MeSO2 |
1119 | 1 | O | 键 | 2-嘧啶基 | EtSO2 |
1120 | 1 | O | 键 | 2-嘧啶基 | PrSO2 |
1121 | 1 | O | 键 | 2-嘧啶基 | PhSO2 |
No. | I | x | E | R5 | R11 |
1122 | 1 | O | 键 | 2-嘧啶基 | 4-Me-PhSO2 |
1123 | 0 | 键 | 1-吡唑基 | Bz | |
1124 | 0 | 键 | 1-吡唑基 | 4-Me-PhC(O) | |
1125 | 0 | 键 | 1-吡唑基 | MeSO2 | |
1126 | 0 | 键 | 1-吡唑基 | EtSO2 | |
1127 | 0 | 键 | 1-吡唑基 | PrSO2 | |
1128 | 0 | 键 | 1-吡唑基 | PhSO2 | |
1129 | 0 | 键 | 1-吡唑基 | 4-Me-PhSO2 |
表16:其中取代基及下标定义如下的式(I)化合物:
A=SO2 B=CH2-CH2 R1=CH3
R2=CH3 R3=H R4=H
R7=H Y=CH2 Z=CH2
Q=式(II)的基 v=1
No. | I | x | E | R5 | R6 |
1130 | 1 | O | 键 | 1,4-二嗪基 | MeS |
1131 | 1 | O | 键 | 1,4-二嗪基 | EtS |
1132 | 1 | O | 键 | 1,4-二嗪基 | PrS |
1133 | 1 | O | 键 | 1,4-二嗪基 | MeSO2 |
1134 | 1 | O | 键 | 1,4-二嗪基 | EtSO2 |
1135 | 1 | O | 键 | 2-嘧啶基 | MeS |
1136 | 1 | O | 键 | 2-嘧啶基 | EtS |
1137 | 1 | O | 键 | 2-嘧啶基 | PrS |
1138 | 1 | O | 键 | 2-嘧啶基 | MeSO2 |
1139 | 1 | O | 键 | 2-嘧啶基 | EtSO2 |
1140 | 0 | 键 | 1-吡唑基 | MeS | |
1141 | 0 | 键 | 1-吡唑基 | EtS | |
1142 | 0 | 键 | 1-吡唑基 | PrS | |
1143 | 0 | 键 | 1-吡唑基 | MeSO2 | |
1144 | 0 | 键 | 1-吡唑基 | EtSO2 |
表17:其中取代基及下标定义如下的式(I)化合物:
A=SO2 B=CH2 R3=H
R4=H R6=OH Y=CH2
Z=CH2 v=1 w=0
Q=式(II)的基
No. | R1 | R2 | I | x | E | R5 | 物理数据 |
1145 | Me | Me | 0 | 键 | 1-吡唑基 | 1H NMR(CDCl3):δ1.9(m,3H),2.05(m,2H),2.42(m,2H),2.65(s,3H),2.8(m,2H),3.65(m,1H),3.98(m,1H),6.25(m,1H),6.28(m,1H),7.1(s,1H),7.2(m,1H),7.59(m,1H) | |
1146 | Me | Me | 0 | 键 | 1,2,3-三唑-1-基 | ||
1147 | Me | Me | 1 | O | 键 | Ph | 1H NMR(CDCl3):δ2.05(m,2H),2.18(s,3H),2.42(m,2H),2.6(m,2H),2.8(m,2H),3.65(m,2H),4.58(s,2H),5.38(m,1H),7.01(s,1H),7.35(m,5H) |
1148 | Me | Me | 1 | O | 键 | 2-嘧啶基 | |
1149 | Me | Me | 1 | O | 键 | 1,4-二嗪基 | |
1150 | Me | Me | 1 | O | 键 | 3-氰基-2-吡啶基 | |
1151 | Me | H | 0 | 键 | 1-吡唑基 | ||
1152 | Me | H | 0 | 键 | 1,2,4-吡唑-1-基 | ||
1153 | Me | H | 1 | O | 键 | Ph | |
1154 | Me | H | 1 | O | 键 | 2-嘧啶基 | |
1155 | Me | H | 1 | O | 键 | 1,4-二嗪基 | |
1156 | Me | H | 1 | O | 键 | 3-氰基-2-吡啶基 | |
1157 | Me | Cl | 0 | 键 | 1-吡唑基 |
No. | R1 | R2 | I | x | E | R5 | 物理数据 |
1158 | Me | Cl | 0 | 键 | 1,2,4-吡唑-1-基 | ||
1159 | Me | Cl | 1 | O | 键 | Ph | |
1160 | Me | Cl | 1 | O | 键 | 2-嘧啶基 | |
1161 | Me | Cl | 1 | O | 键 | 1,4-二嗪基 | |
1162 | Me | Cl | 1 | O | 键 | 3-氰基-2-吡啶基 | |
1163 | Cl | Cl | 0 | 键 | 1-吡唑基 | ||
1164 | Cl | Cl | 0 | 键 | 1,2,4-吡唑-1-基 | ||
1165 | Cl | Cl | 1 | O | 键 | Ph | |
1166 | Cl | Cl | 1 | O | 键 | 2-嘧啶基 | |
1167 | Cl | Cl | 1 | O | 键 | 1,4-二嗪基 | |
1168 | Cl | Cl | 1 | O | 键 | 3-氰基-2-吡啶基 | |
1169 | Cl | H | 0 | 键 | 1-吡唑基 | ||
1170 | Cl | H | 0 | 键 | 1,2,4-吡唑-1-基 | ||
1171 | Cl | H | 1 | O | 键 | Ph | |
1172 | Cl | H | 1 | O | 键 | 2-嘧啶基 | |
1173 | Cl | H | 1 | O | 键 | 1,4-二嗪基 | |
1174 | Cl | H | 1 | O | 键 | 3-氰基-2-吡啶基 |
B配制实施例
1.喷粉剂
喷粉剂是得自混合10重量份式(1)化合物及作为惰性物质的90重量份滑石,并在锤磨机中将混合物磨成细粉。
2.可分散的粉剂
容易分散于水中的可湿性粉末是得自混合25重量份式(1)化合物、作为惰性物质的64重量份含高岭土的石英、10重量份木质素磺酸钾及作为湿润剂及分散剂的1重量份油酰基甲基牛磺酸钠,并在棒磨机中将混合物磨碎。
3.分散性浓缩剂
容易分散于水中的分散性浓缩剂是得自混合20重量份式(1)化合物、6重量份烷基苯酚聚乙二醇醚(_Triton X 207)、3重量份异十三醇聚乙二醇醚(8EO)及71重量份石蜡矿物油(沸点范围例如约255至约277℃),并在球磨机中将混合物磨成小于5微米的细粉。
4.可乳化性浓缩剂
可乳化性浓缩剂是得自15重量份式(1)化合物、作为溶剂的75重量份环己酮及作为乳化剂的10重量份乙氧基化壬基酚。
5.可分散于水中的颗粒剂
可分散于水中的颗粒剂是得自混合75重量份式(I)化合物、10重量组分木质素磺酸钙、5重量份月桂基硫酸钠、3重量份聚乙烯醇及7重量份高岭土,在棒磨机中将混合物磨碎,在流化床中用水作为粒化液体而将其粒化。
可分散于水中的颗粒剂也可得自在胶体研磨机中将25重量份式(I)化合物、5重量份2,2’-二萘基甲烷-6,6’-二磺酸钠、2重量份油酰甲基牛磺酸钠、1重量份聚乙烯醇、17重量份碳酸钙及50重量份水均匀化及预磨成细粉,随后在珠磨机中粉碎混合物并在喷雾塔中借助单物质喷嘴将所得的悬浮液雾化并干燥。
C.生物实施例
1.发芽前对杂草的活性
将单子叶或双子叶杂草类植物的种子置于纸板盆的砂质壤土中并用土覆盖,然后在每公倾1公斤或更少的活性物质的剂量下,将配制成可湿性粉末或悬浮浓缩物的根据本发明的化合物,以含水悬浮液或乳化液的形式施加在土壤表面上,水使用量为600至800升水/公顷(已换算)。处理后将盆子置放于温室中并保持在杂草的良好成长环境下,受测植物发芽后,经过3至4周的测试时间,与未经处理的对照组比较目视记录对植物所造成的伤害及对发芽的负面效应,在此,例如实例编号7及11的化合物对繁缕、野燕麦、多花黑麦草及狗尾草显示至少80%的活性,实例编号2、3、4、7、11及12的化合物对反枝苋、Sinapis arvensis及狗尾草显示至少90%的活性,实例编号1、2、6、7和的化合物对反枝苋及繁缕显示100%的活性。
2.发芽后对杂草的活性
将单子叶或双子叶杂草类植物的种子置于纸板盆的砂质土壤中并用土覆盖,置于良好成长环境下的温室中成长,播种后二至三周,受测植物在三叶阶段加以处理。在每公顷1公斤或更少的活性物质的剂量下(已换算过),将配制成可湿性粉末或悬浮浓缩物的根据本发明的化合物以600至800升水/公顷(已换算过)的水使用量喷洒于植物的绿色部位,当受测植物在温室中的最佳成长情形下保持约3至4周后,与未经处理的对照组比较,目视记录制剂的活性,在发芽后,根据本发明的化合物对重要经济性的广泛禾草类杂草及阔叶杂草具有良好的除草活性。例如实例编号3、9、10、11及12的化合物对Sinapis arvensis显示至少90%的活性,实例编号1、4、7及10的化合物对繁缕及狗尾草显示至少80%的活性,实例编号6及9的化合物对野燕麦及反枝苋显示至少80%的活性。
3.在稻田中对有害的植物的活性
将典型在稻田中的有害植物栽培在水稻情形下的温室内(水的高度为2-3公分),在每公顷1公斤或更少的活性物质的剂量下(已换算过),用根据本发明配制的化合物处理后,将测试植物于温室中置于最佳的生长情形下并在整个测试期间保持在这些情形下,约三周后,与未经处理的对照组比较,目视评定植物的伤害程度,根据本发明的化合物对有害的植物有非常良好的除草活性。例如实例编号2、4、7、11及12的化合物对碎米莎草及稗显示至少80%的活性。
4.作物的忍受度
在进一步的温室实验中,将多种作物及杂草置于砂质壤土中并用土覆盖,部分盆子立即以第1节所叙述的方式处理,剩下的其他盆子置于温室中直到植物长出二至三片真实叶子时,喷洒不同剂量根据本发明化学式(I)的物质,如第2节所述。施用和在温室中放置四至五周后目视评定,结果显示根据本发明的化合物在发芽前或后使用时,即使使用高剂量的活性物质,也不会对双子叶作物如大豆及甜菜造成任何伤害。而且部分物质也对禾本科作物如大麦、小麦及稻无害。部分式(I)化合物显现高选择性,且因此适合在农业作物中供控制不要的植物生长。
Claims (12)
1.一种式(I)的苯甲酰衍生物
其中
Q为式(II)、(III)或(IV)的基团
R1、R2彼此独立地为氢或(C1-C4)-烷基;
R3和R4为氢;
R5为苯基、含有1或2个氮原子作为环单元的6元杂芳基或含有2或3个氮原子作为环单元的5元杂芳基,其中上述苯基或杂芳基是未取代的或被1或2个选自下组的取代基取代:卤素、三氟甲基、甲氧基或氰基;
或,如果E是一个键且l是0,R5还可以是羟基,-O-N=CR1Rm、-P(=O)(ORi)(ORk);
R6是(C1-C4)烷基磺酰基或OH;
A是SO2;
B是CH2或CH2CH2;
E是一个键或CH2;
X是氧或硫;
Y和Z是CHR7;
R7、R8和R10相互独立地是氢或(C1-C4)-烷基;
G1-G2是选自下组的二价单元:OCR9、SCR9和NR10COR11,其中进行连接至环体系以使此二价单元的碳原子在各情形下是经双键连接至环体系的碳原子;
R9是(C3-C8)环烷基;
R11是氢;
Ri和Rk相互独立地是(C1-C4)烷基;
Rl和Rm相互独立地是(C1-C4)烷基;或
Rl和Rm与它们相连的碳原子一起形成5或6元饱和碳环;
l为0或1;
v是1;
w是0、1或2;
前提条件是:
如果E为亚甲基,且在G1-G2中的G1为硫,则R5不是苯基。
2.权利要求1的苯甲酰衍生物,其中
B是CH2CH2;
R6是OH;
G1-G2是OCR9或NR10COR11;
R8是氢;
R9是(C3-C6)环烷基;
R10是(C1-C3)烷基。
3.权利要求1或2的苯甲酰衍生物,其中Q是式(II)或(III)基团
5.一种除草剂组合物,其中含至少一种权利要求1的式(I)化合物。
6.权利要求5的除草剂组合物,其还含有配制助剂。
7.一种控制不想要的植物的方法,其中将有效量的至少一种权利要求1的式(I)化合物施加至植物或不想要的植物的生长区域。
8.一种控制不想要的植物的方法,其中将有效量的至少一种权利要求5的除草剂组合物施加至植物或不想要的植物的生长区域。
9.权利要求1的苯甲酰衍生物用于控制不想要的植物的用途。
10.权利要求5的除草剂组合物用于控制不想要的植物的用途。
11.权利要求9或10的用途,其中在有用植物的栽培中控制不想要的植物。
12.权利要求11的用途,其中有用的植物为转基因的有用的植物。
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DE19840337.2 | 1998-09-04 | ||
DE19840337A DE19840337A1 (de) | 1998-09-04 | 1998-09-04 | Benzoylderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
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CN1149211C true CN1149211C (zh) | 2004-05-12 |
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US (1) | US6297196B1 (zh) |
EP (1) | EP1109807A1 (zh) |
JP (1) | JP2002524459A (zh) |
KR (1) | KR20010085762A (zh) |
CN (1) | CN1149211C (zh) |
AR (1) | AR020376A1 (zh) |
AU (1) | AU752786B2 (zh) |
BR (1) | BR9913461A (zh) |
CA (1) | CA2343151A1 (zh) |
CO (1) | CO5210935A1 (zh) |
CZ (1) | CZ2001796A3 (zh) |
DE (1) | DE19840337A1 (zh) |
HU (1) | HUP0104201A3 (zh) |
ID (1) | ID29626A (zh) |
IL (1) | IL141374A0 (zh) |
MY (1) | MY130252A (zh) |
PL (1) | PL346496A1 (zh) |
RU (1) | RU2223271C2 (zh) |
SK (1) | SK2962001A3 (zh) |
TR (1) | TR200100695T2 (zh) |
TW (1) | TW585863B (zh) |
UA (1) | UA68395C2 (zh) |
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DE69938171T2 (de) | 1998-12-11 | 2008-05-29 | Daicel Chemical Industries, Ltd. | Verfahren zur herstellung von organischen verbindungen mit imid-katalysatoren |
DE19950943A1 (de) | 1999-10-22 | 2001-05-17 | Aventis Cropscience Gmbh | Synergistische herbizide Mittel enthaltend Herbizide aus der Gruppe der Hemmstoffe der Hydroxyphenylpyruvat-Dioxygenase |
WO2007079346A2 (en) * | 2005-12-30 | 2007-07-12 | Olsen Christopher J | Articulated wheel assemblies and vehicles therewith |
WO2008014430A1 (en) | 2006-07-27 | 2008-01-31 | Emisphere Technologies, Inc. | Arylsulfanyl compounds and compositions for delivering active agents |
US8334236B2 (en) | 2009-02-03 | 2012-12-18 | Kumiai Chemical Industry Co., Ltd. | Ring-fused 2-pyridone derivatives and herbicides |
CN103596945B (zh) | 2011-03-15 | 2016-04-13 | 拜耳知识产权有限责任公司 | N-(1,2,5-噁二唑-3-基)-、n-(四唑-5-基)-和n-(三唑-5-基)双环芳基-羧酰胺及其作为除草剂的用途 |
CN103992301B (zh) * | 2014-05-09 | 2016-01-13 | 上海大学 | 2-羟基-5-氧代-4-芳基-2-三氟甲基-3,4,5,6,7,8-六氢-2h-色烯-3-羧酸乙酯化合物的制备方法 |
JP2018524336A (ja) | 2015-07-01 | 2018-08-30 | シンジェンタ パーティシペーションズ アーゲー | 硫黄含有置換基を有する有害生物防除に活性な多環式誘導体 |
CN108026086B (zh) * | 2015-07-24 | 2021-02-19 | 拜耳作物科学股份公司 | 取代的呋喃并/噻吩并环烷基氨基-2-嘧啶衍生物及其用于防治不想要的植物生长的用途 |
CN107398300B (zh) * | 2017-07-24 | 2020-08-21 | 中国科学院化学研究所 | 芳香族酰胺芳环c-h键直接氨基化反应的方法 |
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WO1993018031A1 (en) * | 1992-03-03 | 1993-09-16 | Idemitsu Kosan Co., Ltd. | Pyrazole derivative |
CA2117413C (en) * | 1993-07-30 | 2006-11-21 | Neil Geach | Herbicidal isoxazole-4-yl-methanone derivatives |
HUT74306A (en) | 1993-11-09 | 1996-12-30 | Idemitsu Kosan Co | Pyrazole derivatives and herbicide containing the same |
GB9405229D0 (en) * | 1994-03-17 | 1994-04-27 | Rhone Poulenc Agriculture | Compositions of matter |
CA2193212A1 (en) * | 1994-06-27 | 1996-01-04 | Ichiro Nasuno | Herbicidal composition |
BR9607396A (pt) * | 1995-02-15 | 1998-06-30 | Idemitsu Kosan Co | Derivados de isoxazola |
BR9604847A (pt) | 1995-04-05 | 1998-06-16 | Idemitsu Kosan Co | Derivados de pirazol |
WO1997008164A1 (en) * | 1995-08-25 | 1997-03-06 | E.I. Du Pont De Nemours And Company | Bicyclic herbicides |
EP0970956A1 (en) * | 1995-10-04 | 2000-01-12 | Idemitsu Kosan Company Limited | Pyrazole derivatives |
WO1997013765A1 (fr) * | 1995-10-09 | 1997-04-17 | Idemitsu Kosan Co., Ltd. | Derives de 2-cyano-1,3-dione et herbicides dont ils constituent le principe actif |
WO1997023135A1 (fr) * | 1995-12-25 | 1997-07-03 | Idemitsu Kosan Co., Ltd. | Composition herbicide |
US6297198B1 (en) * | 1996-05-14 | 2001-10-02 | Syngenta Participations Ag | Isoxazole derivatives and their use as herbicides |
US6037312A (en) * | 1996-05-23 | 2000-03-14 | Idemitsu Kosan Co., Ltd. | Isoxazole derivatives |
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- 1999-08-26 WO PCT/EP1999/006259 patent/WO2000014087A1/de not_active Application Discontinuation
- 1999-08-26 CN CNB998105945A patent/CN1149211C/zh not_active Expired - Fee Related
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RU2223271C2 (ru) | 2004-02-10 |
EP1109807A1 (de) | 2001-06-27 |
BR9913461A (pt) | 2001-07-24 |
CO5210935A1 (es) | 2002-10-30 |
CZ2001796A3 (cs) | 2001-08-15 |
ID29626A (id) | 2001-09-06 |
DE19840337A1 (de) | 2000-03-09 |
HUP0104201A2 (hu) | 2002-03-28 |
HUP0104201A3 (en) | 2002-04-29 |
CA2343151A1 (en) | 2000-03-16 |
UA68395C2 (en) | 2004-08-16 |
PL346496A1 (en) | 2002-02-11 |
AR020376A1 (es) | 2002-05-08 |
WO2000014087A1 (de) | 2000-03-16 |
KR20010085762A (ko) | 2001-09-07 |
ZA200101563B (en) | 2002-05-10 |
SK2962001A3 (en) | 2001-11-06 |
IL141374A0 (en) | 2002-03-10 |
TW585863B (en) | 2004-05-01 |
MY130252A (en) | 2007-06-29 |
AU752786B2 (en) | 2002-10-03 |
AU5855199A (en) | 2000-03-27 |
TR200100695T2 (tr) | 2001-07-23 |
CN1317004A (zh) | 2001-10-10 |
US6297196B1 (en) | 2001-10-02 |
JP2002524459A (ja) | 2002-08-06 |
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