TW202346271A - 除草化合物 - Google Patents
除草化合物 Download PDFInfo
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- TW202346271A TW202346271A TW112102342A TW112102342A TW202346271A TW 202346271 A TW202346271 A TW 202346271A TW 112102342 A TW112102342 A TW 112102342A TW 112102342 A TW112102342 A TW 112102342A TW 202346271 A TW202346271 A TW 202346271A
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- TW
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- Prior art keywords
- nhso
- alkyl
- chme
- hydrogen
- och
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 192
- 230000002363 herbicidal effect Effects 0.000 title claims description 17
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 239000000460 chlorine Substances 0.000 claims description 188
- 239000001257 hydrogen Substances 0.000 claims description 97
- 229910052739 hydrogen Inorganic materials 0.000 claims description 97
- 239000000203 mixture Substances 0.000 claims description 84
- -1 C 1 -C 4 alkoxy Chemical group 0.000 claims description 74
- 229910052760 oxygen Inorganic materials 0.000 claims description 51
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 43
- 239000001301 oxygen Substances 0.000 claims description 43
- 229910052717 sulfur Inorganic materials 0.000 claims description 41
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 38
- 239000011593 sulfur Substances 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 229910052801 chlorine Inorganic materials 0.000 claims description 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
- 229910052736 halogen Inorganic materials 0.000 claims description 25
- 150000002367 halogens Chemical class 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 21
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 18
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 17
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 16
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 11
- 150000001721 carbon Chemical group 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 239000011737 fluorine Substances 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- 150000001336 alkenes Chemical class 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 125000006833 (C1-C5) alkylene group Chemical group 0.000 claims description 3
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- 150000001204 N-oxides Chemical class 0.000 claims description 2
- 239000012872 agrochemical composition Substances 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 14
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 239000004009 herbicide Substances 0.000 abstract description 20
- 239000000575 pesticide Substances 0.000 abstract description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 180
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 64
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 60
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- 238000006243 chemical reaction Methods 0.000 description 33
- 241000196324 Embryophyta Species 0.000 description 32
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- 239000004480 active ingredient Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 239000002904 solvent Substances 0.000 description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 22
- 239000003921 oil Substances 0.000 description 20
- 235000019198 oils Nutrition 0.000 description 20
- 239000007787 solid Substances 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 238000009472 formulation Methods 0.000 description 14
- 239000003112 inhibitor Substances 0.000 description 14
- 239000002671 adjuvant Substances 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 125000001309 chloro group Chemical group Cl* 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 12
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- 239000002253 acid Substances 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 8
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 239000005531 Flufenacet Substances 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 240000008042 Zea mays Species 0.000 description 7
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 7
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 235000005822 corn Nutrition 0.000 description 7
- 244000038559 crop plants Species 0.000 description 7
- IANUJLZYFUDJIH-UHFFFAOYSA-N flufenacet Chemical compound C=1C=C(F)C=CC=1N(C(C)C)C(=O)COC1=NN=C(C(F)(F)F)S1 IANUJLZYFUDJIH-UHFFFAOYSA-N 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- 241001542006 Amaranthus palmeri Species 0.000 description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
- 150000002430 hydrocarbons Chemical group 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 150000003573 thiols Chemical class 0.000 description 6
- 235000013311 vegetables Nutrition 0.000 description 6
- XEJNEDVTJPXRSM-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-5-methyl-4,5-dihydro-1H-pyrazole-3,5-dicarboxylic acid Chemical compound OC(=O)C1(C)CC(C(O)=O)=NN1C1=CC=C(Cl)C=C1Cl XEJNEDVTJPXRSM-UHFFFAOYSA-N 0.000 description 5
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- 235000004977 Brassica sinapistrum Nutrition 0.000 description 5
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- 244000058871 Echinochloa crus-galli Species 0.000 description 5
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- 239000002202 Polyethylene glycol Substances 0.000 description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 235000012211 aluminium silicate Nutrition 0.000 description 5
- 125000001246 bromo group Chemical group Br* 0.000 description 5
- ICJSJAJWTWPSBD-UHFFFAOYSA-N cloquintocet Chemical compound C1=CN=C2C(OCC(=O)O)=CC=C(Cl)C2=C1 ICJSJAJWTWPSBD-UHFFFAOYSA-N 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 238000010353 genetic engineering Methods 0.000 description 5
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 5
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- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- PMNLUUOXGOOLSP-UHFFFAOYSA-M 2-sulfanylpropanoate Chemical compound CC(S)C([O-])=O PMNLUUOXGOOLSP-UHFFFAOYSA-M 0.000 description 4
- 240000006122 Chenopodium album Species 0.000 description 4
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- 108020004705 Codon Proteins 0.000 description 4
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- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
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- PYCINWWWERDNKE-UHFFFAOYSA-N 1-(2-chloro-6-propylimidazo[1,2-b]pyridazin-3-yl)sulfonyl-3-(4,6-dimethoxypyrimidin-2-yl)urea Chemical compound N12N=C(CCC)C=CC2=NC(Cl)=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 PYCINWWWERDNKE-UHFFFAOYSA-N 0.000 description 3
- KPSTXQYTZBZXMM-UHFFFAOYSA-N 2-[8-chloro-4-(4-methoxyphenyl)-3-oxoquinoxaline-2-carbonyl]cyclohexane-1,3-dione Chemical compound C1=CC(OC)=CC=C1N1C(=O)C(C(=O)C2C(CCCC2=O)=O)=NC2=C(Cl)C=CC=C21 KPSTXQYTZBZXMM-UHFFFAOYSA-N 0.000 description 3
- MONMFXREYOKQTI-UHFFFAOYSA-M 2-bromopropanoate Chemical compound CC(Br)C([O-])=O MONMFXREYOKQTI-UHFFFAOYSA-M 0.000 description 3
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- KPUREKXXPHOJQT-UHFFFAOYSA-N mesotrione Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O KPUREKXXPHOJQT-UHFFFAOYSA-N 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- XHFGWHUWQXTGAT-UHFFFAOYSA-N n-methylpropan-2-amine Chemical compound CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
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- GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 2
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- 229940037312 stearamide Drugs 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- PZTAGFCBNDBBFZ-UHFFFAOYSA-N tert-butyl 2-(hydroxymethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1CO PZTAGFCBNDBBFZ-UHFFFAOYSA-N 0.000 description 1
- DRDVJQOGFWAVLH-UHFFFAOYSA-N tert-butyl n-hydroxycarbamate Chemical compound CC(C)(C)OC(=O)NO DRDVJQOGFWAVLH-UHFFFAOYSA-N 0.000 description 1
- QQDYOLJZDUADHV-CJNGLKHVSA-N tetflupyrolimet Chemical compound FC1=C(C=CC=C1)NC(=O)[C@H]1C(N(C[C@@H]1C1=CC(=CC=C1)C(F)(F)F)C)=O QQDYOLJZDUADHV-CJNGLKHVSA-N 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- SZWHXXNVLACKBV-UHFFFAOYSA-N tetraethylphosphanium Chemical compound CC[P+](CC)(CC)CC SZWHXXNVLACKBV-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- RTONGXWQCWZDSR-UHFFFAOYSA-N tetrahydrofuran-2-ylmethyl 2-[(4-amino-3,5-dichloro-6-fluoropyridin-2-yl)oxy]propanoate Chemical compound CC(C(OCC1OCCC1)=O)OC(N=C(C(Cl)=C1N)F)=C1Cl RTONGXWQCWZDSR-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- BXYHVFRRNNWPMB-UHFFFAOYSA-N tetramethylphosphanium Chemical compound C[P+](C)(C)C BXYHVFRRNNWPMB-UHFFFAOYSA-N 0.000 description 1
- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
- XOGCTUKDUDAZKA-UHFFFAOYSA-N tetrapropylphosphanium Chemical compound CCC[P+](CCC)(CCC)CCC XOGCTUKDUDAZKA-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 229960002178 thiamazole Drugs 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- XDQXIEKWEFUDFK-UHFFFAOYSA-N tributylsulfanium Chemical compound CCCC[S+](CCCC)CCCC XDQXIEKWEFUDFK-UHFFFAOYSA-N 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- 229960002415 trichloroethylene Drugs 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- WCZKTXKOKMXREO-UHFFFAOYSA-N triethylsulfanium Chemical compound CC[S+](CC)CC WCZKTXKOKMXREO-UHFFFAOYSA-N 0.000 description 1
- AZHZOGYUMMIAOF-UHFFFAOYSA-N trifludimoxazin Chemical compound O=C1N(C)C(=S)N(C)C(=O)N1C(C(=C1)F)=CC2=C1OC(F)(F)C(=O)N2CC#C AZHZOGYUMMIAOF-UHFFFAOYSA-N 0.000 description 1
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- NRZWQKGABZFFKE-UHFFFAOYSA-N trimethylsulfonium Chemical compound C[S+](C)C NRZWQKGABZFFKE-UHFFFAOYSA-N 0.000 description 1
- YRYSAWZMIRQUBO-UHFFFAOYSA-N trimethylsulfoxonium Chemical compound C[S+](C)(C)=O YRYSAWZMIRQUBO-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- QFKMMXYLAPZKIB-UHFFFAOYSA-N undecan-1-amine Chemical compound CCCCCCCCCCCN QFKMMXYLAPZKIB-UHFFFAOYSA-N 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000004565 water dispersible tablet Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000012991 xanthate Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/30—Only oxygen atoms
- C07D251/32—Cyanuric acid; Isocyanuric acid
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
- A01N43/68—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms with two or three nitrogen atoms directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P13/00—Herbicides; Algicides
Abstract
可用作殺有害生物劑、尤其是除草劑的具有式 (I) 的化合物或其農藝學上可接受的鹽:其中取代基係如在請求項1中所定義的。
Description
本發明關於具有除草活性的三𠯤衍生物,以及用於製備此類衍生物之方法和中間體。本發明進一步延伸到包含此類衍生物的除草組成物,並且延伸到此類化合物和組成物在有用植物的作物中用於控制不希望的植物生長之用途,特別是用於控制雜草之用途。
WO 2019/121543、WO 2021/018664和WO 2021/259224均揭露了與本發明的除草化合物類似的除草化合物。
本發明基於以下發現:如在本文所定義的具有式 (I) 的三𠯤衍生物展現了出人意料地良好的除草活性。因此,根據本發明,提供了一種具有式 (I) 的化合物或其農藝學上可接受的鹽:
(I)
其中
X
1、X
2和X
3各自獨立地選自氧和硫;
Y係C-H或氮;
B係O、S、或NR
5;
D係(CR
6R
7)
n;
m係從0至2的整數;
n係從1至4的整數;
R
1係氫或C
1-C
6烷基;
R
2係氫、胺基、C
1-C
6烷基、C
3-C
6烯基或C
3-C
6炔基;
R
3係氫、鹵素、C
1-C
4烷基、C
1-C
4鹵代烷基、C
1-C
4烷氧基、C
1-C
4鹵代烷氧基、C
1-C
4烷硫基或C
1-C
4烷基磺醯基;
R
4係氫、鹵素、氰基、硝基、胺基羰基、胺基硫代羰基、C
1-C
4烷基、C
1-C
4鹵代烷基、C
1-C
4烷氧基、C
1-C
4鹵代烷氧基或C
1-C
4烷基磺醯基;
R
5係氫、羥基、C
1-C
6烷基或C
1-C
4烷氧基;
R
6和R
7各自獨立地選自氫、鹵素、C
1-C
6烷基、C
1-C
6鹵代烷基、羥基、C
1-C
4烷氧基、C
1-C
4烷氧基羰基或CH
2OR
12;前提係R
6和R
7在同一碳原子上不皆為羥基;
或者,在同一碳原子或不同碳原子上的兩個基團R
6和R
7一起形成C
1-C
5伸烷基鏈,該鏈含有0、1或2個氧原子,被1-3個基團R
15取代;
或者,在同一碳原子上的兩個基團R
6和R
7與它們所附接的碳一起形成C
2烯烴;
R
8係OR
9、SR
9或NR
10R
11;
R
9係氫、C
1-C
10烷基、C
1-C
10鹵代烷基、C
3-C
6烯基、C
3-C
6鹵代烯基、C
3-C
6炔基、C
1-C
4烷氧基C
1-C
6烷基、C
1-C
4鹵代烷氧基C
1-C
6烷基、C
6-C
10芳基C
1-C
3烷基、被1-4個基團R
13取代的C
6-C
10芳基C
1-C
3烷基、雜芳基C
1-C
3烷基或被1-3個基團R
13取代的雜芳基C
1-C
3烷基;
R
10係氫、C
1-C
6烷基或SO
2R
14;
R
11係氫或C
1-C
6烷基;或者
R
10和R
11與它們所附接的氮一起形成3員至6員雜環基環,該雜環基環視需要含有氧原子;
R
12係氫、C
1-C
4烷基或C
1-C
4烷基羰基;
R
13各自獨立地選自鹵素、C
1-C
4烷基、C
1-C
4鹵代烷基、C
1-C
4烷氧基、C
1-C
4鹵代烷氧基、氰基和C
1-C
4烷基磺醯基;
R
14係C
1-C
4烷基、C
1-C
4鹵代烷基或C
1-C
4烷基(C
1-C
4烷基)胺基;
R
15各自獨立地選自氫、鹵素、C
1-C
4烷基和C
1-C
4鹵代烷基;
R
16和R
17獨立地選自氫、鹵素、C
1-C
6烷基、C
1-C
6鹵代烷基、C
1-C
4烷氧基和CH
2OR
12;
或者,兩個基團R
16和R
17一起形成C
2-C
5伸烷基鏈,該伸烷基鏈含有0、1或2個氧原子,被1-3個基團R
15取代;
或者,兩個基團R
16和R
17與它們所附接的碳一起形成C
2烯烴;
或其鹽或N-氧化物。
根據本發明之第二方面,提供了一種農用化學組成物,其包含除草有效量的具有式 (I) 的化合物和農用化學上可接受的稀釋劑或載劑。這樣一種農業組成物可以進一步包含至少一種另外的活性成分。
根據本發明之第三方面,提供了一種用於控制或預防不希望的植物生長之方法,其中將除草有效量的具有式 (I) 的化合物或包含這種化合物作為活性成分的組成物施用至該植物、其部分或其場所。
根據本發明之第四方面,提供了具有式 (I) 的化合物作為除草劑之用途。
根據本發明之第五方面,提供了一種用於製備具有式 (I) 的化合物之方法。
如本文使用的,術語「鹵素(halogen或halo)」係指氟(fluorine,fluoro)、氯(chlorine,chloro)、溴(bromine,bromo)或碘(iodine,iodo),較佳的是氟、氯或溴。
如本文使用的,氰基意指-CN基團。
如本文使用的,羥基意指-OH基團。
如本文使用的,硝基意指-NO
2基團。
如本文使用的,胺基意指-NH
2基團。
如本文使用的,術語「C
1-C
10烷基」係指僅由碳原子和氫原子組成的直鏈的或支鏈的烴鏈基團,該烴鏈基團不含不飽和度、具有從一至十個碳原子、並且藉由單鍵附接至分子的其餘部分。C
1-C
6烷基、C
1-C
4烷基和C
1-C
2烷基應相應地解釋。C
1-C
10烷基的實例包括但不限於甲基(Me)、乙基(Et)、正丙基、1-甲基乙基(異丙基)、正丁基和1-二甲基乙基(三級丁基)。
如本文使用的,術語「C
1-C
4烷氧基」係指具有式-OR
a的基團,其中R
a係如上一般定義的C
1-C
4烷基基團。C
1-C
3烷氧基應相應地解釋。C
1-4烷氧基的實例包括但不限於甲氧基、乙氧基、丙氧基、異丙氧基和三級丁氧基。
如本文使用的,術語「C
1-C
10鹵代烷基」係指如上一般定義的C
1-C
10烷基基團,其被一個或多個相同或不同的鹵素原子取代。C
1-C
6鹵代烷基和C
1-C
4鹵代烷基應相應地解釋。C
1-C
10鹵代烷基的實例包括但不限於氯甲基、氟甲基、氟乙基、二氟甲基、三氟甲基和2,2,2-三氟乙基。
如本文使用的,術語「C
2-C
6烯基」係指僅由碳原子和氫原子組成的直鏈或支鏈的烴鏈基團,該烴鏈基團含有至少一個可以具有 (
E)- 或 (
Z)-組態的雙鍵,具有從二至六個碳原子,藉由單鍵附接至分子的其餘部分。C
3-C
6烯基和C
2-C
4烯基應相應地解釋。C
2-C
6烯基的實例包括但不限於丙-1-烯基、烯丙基(丙-2-烯基)和丁-1-烯基。
如本文使用的,術語「C
2-C
6鹵代烯基」係指被一個或多個相同的或不同的鹵素原子取代的如上一般定義的C
2-C
6烯基基團。C
3-C
6鹵代烯基和C
2-C
4鹵代烯基應相應地解釋。C
2-C
6鹵代烯基的實例包括但不限於氯乙烯、氟乙烯、1,1-二氟乙烯、1,1-二氯乙烯和1,1,2-三氯乙烯。
如本文使用的,術語「C
2-C
6炔基」係指僅由碳原子和氫原子組成的直鏈或支鏈的烴鏈基團,該烴鏈基團包含至少一個三鍵,具有從二至六個碳原子,並且藉由單鍵附接至分子的其餘部分。C
3-C
6炔基和C
2-C
4炔基應相應地解釋。C
2-C
6炔基的實例包括但不限於丙-1-炔基、炔丙基(丙-2-炔基)和丁-1-炔基。
如本文使用的,術語「C
1-C
4鹵代烷氧基」係指被一個或多個相同的或不同的鹵素原子取代的如上所定義的C
1-C
4烷氧基基團。C
1-C
3鹵代烷氧基應相應地解釋。C
1-C
4鹵代烷氧基的實例包括但不限於氟甲氧基、二氟甲氧基、氟乙氧基、三氟甲氧基和三氟乙氧基。
如本文使用的,術語「C
1-C
4鹵代烷氧基C
1-C
6烷基」係指具有式R
b-O-R
a-的基團,其中R
b係如上一般定義的C
1-C
4鹵代烷基基團,並且R
a係如上一般定義的C
1-C
6伸烷基基團。
如本文使用的,術語「C
1-C
4烷氧基C
1-C
6烷基」係指具有式R
b-O-R
a-的基團,其中R
b係如上一般定義的C
1-C
4烷基基團,並且R
a係如上一般定義的C
1-C
6伸烷基基團。
如本文使用的,術語「C
1-C
4烷基羰基」係指具有式-C(O)R
a的基團,其中R
a係如上一般定義的C
1-C
4烷基基團。C
1-C
2烷基羰基應相應地解釋。
如本文使用的,術語「C
1-C
4烷氧基羰基」係指具有式-C(O)OR
a的基團,其中R
a係如上一般定義的C
1-C
4烷基基團。
如本文使用的,術語「胺基羰基」係指具有式-C(O)NH
2的基團。
如本文使用的,術語「胺基硫代羰基」係指具有式-C(S)NH
2的基團。
如本文使用的,術語「C
1-C
4烷硫基」係指具有式-SRa的基團,其中Ra係如上一般定義的C
1-C
4烷基基團。
如本文使用的,術語「C
1-C
4烷基磺醯基」係指具有式-S(O)
2R
a的基團,其中Ra係如上一般定義的C
1-C
4烷基基團。術語「C
1-C
3烷基磺醯基」和「C
1-C
2烷基磺醯基」應相應地解釋。C
1-C
6烷基磺醯基的實例包括但不限於甲基磺醯基。
如本文使用的,術語「C
6-C
10芳基」係指僅由碳原子和氫原子組成的6員至10員芳香族環系統,該芳香族環系統可以是單環的、二環的或三環的。此類環系統的實例包括苯基、萘基或茚基。
如本文使用的,術語「C
6-C
10芳基C
1-C
3烷基」係指如上一般定義的芳基部分,該芳基部分藉由如上所定義的C
1-C
3伸烷基連接基附接至分子的其餘部分。如本文使用的,術語「C
1-C
4烷基(C
1-C
4烷基)胺基」係指具有式R
a(R
b)NH-的基團,其中R
a和R
b均為如上一般定義的C
1-C
4烷基基團。
如本文使用的,除非另外明確說明,術語「雜芳基」係指包含1、2、3或4個單獨地選自氮、氧和硫的雜原子的5員或6員單環芳香族環。該雜芳基基團可以經碳原子或雜原子鍵合至分子的其餘部分。雜芳基的實例包括呋喃基、吡咯基、咪唑基、噻吩基、吡唑基、噻唑基、異噻唑基、㗁唑基、異㗁唑基、三唑基、四唑基、吡𠯤基、嗒𠯤基、嘧啶基或吡啶基。
如本文使用的,除非另外明確說明,術語「雜環基」或「雜環的」係指包含1、2或3個單獨地選自氮、氧和硫的雜原子的穩定的4員至6員非芳香族單環基團。該雜環基基團可以經由碳原子或雜原子鍵合至分子的其餘部分。雜環基的實例包括但不限於吡咯啉基、吡咯啶基、四氫呋喃基、四氫噻吩基、四氫噻喃基、哌啶基、哌𠯤基、四氫哌喃基、二氫異㗁唑基、二氧戊環基、𠰌啉基或δ-內醯胺基(δ-lactamyl)。
在具有式 (I) 的化合物中一個或多個可能的不對稱碳原子的存在意味著該化合物能以手性異構物形式存在,即鏡像異構物或非鏡像異構物的形式。作為圍繞單鍵的受限旋轉的結果,還可能存在阻轉異構物。式 (I) 旨在包括所有那些可能的異構物形式及其混合物。本發明包括具有式 (I) 的化合物的所有那些可能的異構物形式及其混合物。同樣地,式 (I) 旨在包括所有可能的互變異構物(包括內醯胺-內醯亞胺互變異構和酮-烯醇互變異構)(當存在時)。本發明包括具有式 (I) 的化合物的所有可能的互變異構物形式。類似地,在存在雙取代烯烴的情況下,該等能以
E或
Z形式或作為任何比例的二者的混合物而存在。本發明包括具有式 (I) 的化合物的所有該等可能的異構物形式及其混合物。
具有式 (I) 的化合物通常以農藝學上可接受的鹽、兩性離子或農藝學上可接受的兩性離子鹽的形式提供。本發明涵蓋所有此類農藝學上可接受的鹽、兩性離子及其全部比例的混合物。
本發明之合適的農藝學上可接受的鹽可以具有以下陽離子,該陽離子包括但不限於金屬、胺的共軛酸和有機陽離子。合適的金屬的實例包括鋁、鈣、銫、銅、鋰、鎂、錳、鉀、鈉、鐵和鋅。合適的胺的實例包括烯丙胺、氨、戊胺、精胺酸、苯乙苄胺、苄星青黴素(benzathine)、丁烯基-2-胺、丁胺、丁基乙醇胺、環己胺、癸胺、二戊胺、二丁胺、二乙醇胺、二乙胺、二乙三胺、二庚胺、二己胺、二異戊胺、二異丙胺、二甲胺、二辛胺、二丙醇胺、二炔丙胺、二丙胺、十二胺、乙醇胺、乙胺、乙基丁胺、乙二胺、乙基庚胺、乙基辛胺、乙基丙醇胺、十七胺、庚胺、十六胺、己烯基-2-胺、己胺、己基庚胺、己基辛胺、組胺酸、吲哚啉、異戊胺、異丁醇胺、異丁胺、異丙醇胺、異丙胺、離胺酸、葡甲胺、甲氧基乙胺、甲胺、甲基丁胺、甲基乙胺、甲基己胺、甲基異丙胺、甲基壬胺、甲基十八胺、甲基十五胺、𠰌啉、N,N-二乙基乙醇胺、N-甲基哌𠯤、壬胺、十八胺、辛胺、油胺、十五胺、戊烯基-2-胺、苯氧基乙胺、甲基吡啶、哌𠯤、哌啶、丙醇胺、丙胺、丙二胺、吡啶、吡咯啶、二級丁胺、硬脂醯胺、牛脂胺、十四胺、三丁胺、十三胺、三甲胺、三庚胺、三己胺、三異丁胺、三異癸胺、三異丙胺、三甲胺、三戊胺、三丙胺、三(羥甲基)胺基甲烷和十一胺。合適的有機陽離子的實例包括苄基三丁基銨、苄基三甲基銨、苄基三苯基鏻、膽鹼、四丁基銨、四丁基鏻、四乙基銨、四乙基鏻、四甲基銨、四甲基鏻、四丙基銨、四丙基鏻、三丁基鋶、三丁基氧化鋶、三乙基鋶、三乙基氧化鋶、三甲基鋶、三甲基氧化鋶、三丙基鋶和三丙基氧化鋶。
以下清單提供了關於根據本發明之具有式 (I) 的化合物的取代基X
1、X
2、X
3、Y、B、D、m、n、R
1、R
2、R
3、R
4、R
5、R
6、R
7、R
8、R
9、R
10、R
11、R
12、R
13、R
14、R
15、R
16和R
17的定義,包括較佳的定義。對於該等取代基中的任何一個,以下給出的任何定義都可以結合以下或在本文檔中的其他地方給出的任何其他取代基的任何定義。
X
1係氧或硫。較佳的是,X
1係硫。
X
2係氧或硫。較佳的是,X
2係氧。
X
3係氧或硫。較佳的是,X
3係氧。
Y係C-H或氮。較佳的是,Y係C-H。
B係O、S或NR
5。較佳的是,B係O、NH或NMe。更佳的是,B係O或NH。
m係從0至2的整數。較佳的是,m係0或2,更佳的是,m係0。
n係從1至4的整數。較佳的是,n係從1至2的整數,更佳的是,n係2。
R
1係氫或C
1-C
6烷基。較佳的是,R
1為氫或C
1-C
4烷基。更佳的是,R
1係C
1-C
2烷基,並且最佳的是,R
1係甲基。
R
2係氫、胺基、C
1-C
6烷基、C
3-C
6烯基或C
3-C
6炔基。較佳的是,R
2係氫、C
1-C
4烷基或C
3-C
4炔基。更佳的是,R
2係C
1-C
2烷基,並且最佳的是,R
2係甲基。
R
3係氫、鹵素、C
1-C
4烷基、C
1-C
4鹵代烷基、C
1-C
4烷氧基、C
1-C
4鹵代烷氧基、C
1-C
4烷硫基或C
1-C
4烷基磺醯基。較佳的是,R
3係氫、氯、或氟。更佳的是,R
3係氫或氟。還更佳的是,R
3係氟。
R
4係氫、鹵素、氰基、硝基、胺基羰基、胺基硫代羰基、C
1-C
4烷基、C
1-C
4鹵代烷基、C
1-C
4烷氧基、C
1-C
4鹵代烷氧基或C
1-C
4烷基磺醯基。較佳的是,R
4係氫、氯、溴、氰基或胺基硫代羰基。更佳的是,R
4係氯、溴或氰基,並且最佳的是,R
4係氯。
R
5係氫、羥基、C
1-C
6烷基或C
1-C
4烷氧基。較佳的是,R
5係氫或C
1-C
4烷基。更佳的是,R
5係氫或C
1-C
2烷基。甚至更佳的是,R
5係氫或甲基。在一組實施方式中,R
5係氫。
R
6和R
7各自獨立地選自氫、鹵素、C
1-C
6烷基、C
1-C
6鹵代烷基、羥基、C
1-C
4烷氧基、C
1-C
4烷氧基羰基和CH
2OR
12;前提係R
6和R
7在同一碳原子上不皆為羥基;
或者,在同一碳原子或不同碳原子上的兩個基團R
6和R
7一起形成C
1-C
5伸烷基鏈,該鏈含有0、1或2個氧原子,被1-3個基團R
15取代;
或者,在同一碳原子上的兩個基團R
6和R
7與它們所附接的碳一起形成C
2烯烴。較佳的是,R
6和R
7各自獨立地選自氫、鹵素、C
1-C
4烷基和C
1-C
4烷氧基羰基。更佳的是,R
6和R
7各自獨立地選自氫、鹵素和C
1-C
2烷基。最佳的是,R
6和R
7各自獨立地選自氫、氯和甲基。在一個實施方式中,R
6和R
7均是氫。
R
8係OR
9、SR
9或NR
10R
11。較佳的是,R
8係OR
9。在一個實施方式中,R
8係甲氧基。
R
9係氫、C
1-C
10烷基、C
1-C
10鹵代烷基、C
3-C
6烯基、C
3-C
6鹵代烯基、C
3-C
6炔基、C
1-C
4烷氧基C
1-C
6烷基、C
1-C
4鹵代烷氧基C
1-C
6烷基、C
6-C
10芳基C
1-C
3烷基、被1-4個基團R
13取代的C
6-C
10芳基C
1-C
3烷基、雜芳基C
1-C
3烷基或被1-3個基團R
13取代的雜芳基C
1-C
3烷基。較佳的是,R
9選自氫、C
1-C
4烷基、C
1-C
4鹵代烷基、C
1-C
2烷氧基C
1-C
2烷基、苯基C
1-C
2烷基和被1-2個基團R
13取代的苯基C
1-C
2烷基。更佳的是,R
9係氫、C
1-C
4烷基、C
1-C
2烷氧基C
1-C
2烷基或苯基C
1-C
2烷基。還更佳的是,R
9係氫、C
1-C
4烷基或苯基C
1-C
2烷基。甚至更佳的是,R
9係C
1-C
3烷基。在特別較佳的實施方式中,R
9係甲基。
R
10係氫、C
1-C
6烷基或SO
2R
14。較佳的是,R
10係氫或SO
2R
14。更佳的是,R
10係SO
2R
14。
R
11係氫或C
1-C
6烷基。較佳的是,R
11為氫。
R
12係氫、C
1-C
4烷基或C
1-C
4烷基羰基。較佳的是,R
12係氫、C
1-C
2烷基或C
1-C
2烷基羰基。更佳的是,R
12係氫或甲基。
R
13各自獨立地選自鹵素、C
1-C
4烷基、C
1-C
4鹵代烷基、C
1-C
4烷氧基、C
1-C
4鹵代烷氧基、氰基和C
1-C
4烷基磺醯基。較佳的是,R
13選自鹵素、C
1-C
4烷基、C
1-C
4鹵代烷基、C
1-C
4烷氧基、C
1-C
4鹵代烷氧基、氰基和C
1-C
4烷基磺醯基。
R
14係C
1-C
4烷基、C
1-C
4鹵代烷基或C
1-C
4烷基(C
1-C
4烷基)胺基。較佳的是,R
14係C
1-C
4烷基或C
1-C
4烷基(C
1-C
4烷基)胺基。更佳的是,R
14係甲基或異丙基(甲基)胺基。
R
15各自獨立地選自氫、鹵素、C
1-C
4烷基和C
1-C
4鹵代烷基。較佳的是,R
15各自獨立地選自氫、鹵素和C
1-C
2烷基。更佳的是,R
15各自獨立地選自氫和甲基。最佳的是,R
15係氫。
R
16和R
17獨立地選自氫、鹵素、C
1-C
6烷基、C
1-C
6鹵代烷基、C
1-C
4烷氧基和CH
2OR
12。較佳的是,R
16和R
17獨立地選自氫、C
1-C
4烷基和C
1-C
2烷氧基。更佳的是,R
16和R
17獨立地選自氫和C
1-C
2烷基。最佳的是,R
16和R
17獨立地選自氫和甲基。
一個亞組的較佳的化合物係以下化合物,在該化合物中
X
1係硫;
X
2係氧或硫;
X
3係氧;
Y係C-H;
B係O或NH;
m係0;
n係1或2;
R
1係C
1-C
2烷基;
R
2係C
1-C
2烷基;
R
3選自氫、氯和氟;
R
4選自氯、溴和氰基;
R
6和R
7各自獨立地選自氫、鹵素和C
1-C
2烷基;
R
8係OR
9;
R
9選自氫、C
1-C
4烷基、C
1-C
2烷氧基C
1-C
2烷基和苯基C
1-C
2烷基;
R
16和R
17獨立地選自氫和C
1-C
2烷基。
一個亞組的更佳的化合物係以下化合物,在該化合物中
X
1係硫;
X
2係氧;
X
3係氧;
B係NH;
m係0;
n係2;
Y係C-H;
R
1係甲基;
R
2係甲基;
R
3選自氫和氟;
R
4係氯;
R
6和R
7各自獨立地選自氫和甲基;
R
8係OR
9;
R
9選自氫、C
1-C
4烷基和苯基C
1-C
2烷基;
R
16和R
17獨立地選自氫和甲基。
第二亞組的更佳的化合物係以下化合物,在該化合物中
X
1係硫;
X
2係氧;
X
3係氧;
B係O;
m係0;
n係2;
Y係C-H;
R
1係甲基;
R
2係甲基;
R
3選自氫和氟;
R
4係氯;
R
6和R
7各自獨立地選自氫和甲基;
R
8係OR
9;
R
9選自氫、C
1-C
4烷基和苯基C
1-C
2烷基;
R
16和R
17獨立地選自氫和甲基。
在一組較佳的實施方式中,X
1係硫;
X
2係氧;
X
3係氧;
B係O或NH;
m係0;
n係2;
Y係C-H;
R
1係甲基;
R
2係甲基;
R
3係氟;
R
4係氯;
R
6和R
7均是氫;
R
8係甲氧基;
R
16和R
17各自獨立地選自氫和甲基。
實例的表
下表1揭露了1230種具體的具有式 (I) 的化合物,分別標示為化合物1-1至1-1230,其中X
1係硫,X
2和X
3係氧,R
1和R
2係甲基,R
4係氯,R
16和R
17係氫,並且Y係C-H。
化合物編號 | m | R 3 | B | D | R 8 |
1-1 | 0 | H | O | CH 2 | OH |
1-2 | 0 | H | O | CH 2 | OMe |
1-3 | 0 | H | O | CH 2 | OEt |
1-4 | 0 | H | O | CH 2 | OCH 2Ph |
1-5 | 0 | H | O | CH 2 | NH 2 |
1-6 | 0 | H | O | CH 2 | NHEt |
1-7 | 0 | H | O | CH 2 | NHSO 2Me |
1-8 | 0 | H | O | CH 2 | NHSO 2NMe 2 |
1-9 | 0 | H | O | CH 2 | NHSO 2N(Me)(CHMe 2) |
1-10 | 0 | F | O | CH 2 | OH |
1-11 | 0 | F | O | CH 2 | OMe |
1-12 | 0 | F | O | CH 2 | OEt |
1-13 | 0 | F | O | CH 2 | OCH 2Ph |
1-14 | 0 | F | O | CH 2 | NH 2 |
1-15 | 0 | F | O | CH 2 | NHEt |
1-16 | 0 | F | O | CH 2 | NHSO 2Me |
1-17 | 0 | F | O | CH 2 | NHSO 2NMe 2 |
1-18 | 0 | F | O | CH 2 | NHSO 2N(Me)(CHMe 2) |
1-19 | 0 | Cl | O | CH 2 | OH |
1-20 | 0 | Cl | O | CH 2 | OMe |
1-21 | 0 | Cl | O | CH 2 | OEt |
1-22 | 0 | Cl | O | CH 2 | OCH 2Ph |
1-23 | 0 | Cl | O | CH 2 | NH 2 |
1-24 | 0 | Cl | O | CH 2 | NHEt |
1-25 | 0 | Cl | O | CH 2 | NHSO 2Me |
1-26 | 0 | Cl | O | CH 2 | NHSO 2NMe 2 |
1-27 | 0 | Cl | O | CH 2 | NHSO 2N(Me)(CHMe 2) |
1-28 | 0 | H | NH | CH 2 | OH |
1-29 | 0 | H | NH | CH 2 | OMe |
1-30 | 0 | H | NH | CH 2 | OEt |
1-31 | 0 | H | NH | CH 2 | OCH 2Ph |
1-32 | 0 | H | NH | CH 2 | NH 2 |
1-33 | 0 | H | NH | CH 2 | NHEt |
1-34 | 0 | H | NH | CH 2 | NHSO 2Me |
1-35 | 0 | H | NH | CH 2 | NHSO 2NMe 2 |
1-36 | 0 | H | NH | CH 2 | NHSO 2N(Me)(CHMe 2) |
1-37 | 0 | F | NH | CH 2 | OH |
1-38 | 0 | F | NH | CH 2 | OMe |
1-39 | 0 | F | NH | CH 2 | OEt |
1-40 | 0 | F | NH | CH 2 | OCH 2Ph |
1-41 | 0 | F | NH | CH 2 | NH 2 |
1-42 | 0 | F | NH | CH 2 | NHEt |
1-43 | 0 | F | NH | CH 2 | NHSO 2Me |
1-44 | 0 | F | NH | CH 2 | NHSO 2NMe 2 |
1-45 | 0 | F | NH | CH 2 | NHSO 2N(Me)(CHMe 2) |
1-46 | 0 | Cl | NH | CH 2 | OH |
1-47 | 0 | Cl | NH | CH 2 | OMe |
1-48 | 0 | Cl | NH | CH 2 | OEt |
1-49 | 0 | Cl | NH | CH 2 | OCH 2Ph |
1-50 | 0 | Cl | NH | CH 2 | NH 2 |
1-51 | 0 | Cl | NH | CH 2 | NHEt |
1-52 | 0 | Cl | NH | CH 2 | NHSO 2Me |
1-53 | 0 | Cl | NH | CH 2 | NHSO 2NMe 2 |
1-54 | 0 | Cl | NH | CH 2 | NHSO 2N(Me)(CHMe 2) |
1-55 | 0 | H | O | CHMe | OH |
1-56 | 0 | H | O | CHMe | OMe |
1-57 | 0 | H | O | CHMe | OEt |
1-58 | 0 | H | O | CHMe | OCH 2Ph |
1-59 | 0 | H | O | CHMe | NH 2 |
1-60 | 0 | H | O | CHMe | NHEt |
1-61 | 0 | H | O | CHMe | NHSO 2Me |
1-62 | 0 | H | O | CHMe | NHSO 2NMe 2 |
1-63 | 0 | H | O | CHMe | NHSO 2N(Me)(CHMe 2) |
1-64 | 0 | F | O | CHMe | OH |
1-65 | 0 | F | O | CHMe | OMe |
1-66 | 0 | F | O | CHMe | OEt |
1-67 | 0 | F | O | CHMe | OCH 2Ph |
1-68 | 0 | F | O | CHMe | NH 2 |
1-69 | 0 | F | O | CHMe | NHEt |
1-70 | 0 | F | O | CHMe | NHSO 2Me |
1-71 | 0 | F | O | CHMe | NHSO 2NMe 2 |
1-72 | 0 | F | O | CHMe | NHSO 2N(Me)(CHMe 2) |
1-73 | 0 | Cl | O | CHMe | OH |
1-74 | 0 | Cl | O | CHMe | OMe |
1-75 | 0 | Cl | O | CHMe | OEt |
1-76 | 0 | Cl | O | CHMe | OCH 2Ph |
1-77 | 0 | Cl | O | CHMe | NH 2 |
1-78 | 0 | Cl | O | CHMe | NHEt |
1-79 | 0 | Cl | O | CHMe | NHSO 2Me |
1-80 | 0 | Cl | O | CHMe | NHSO 2NMe 2 |
1-81 | 0 | Cl | O | CHMe | NHSO 2N(Me)(CHMe 2) |
1-82 | 0 | H | NH | CHMe | OH |
1-83 | 0 | H | NH | CHMe | OMe |
1-84 | 0 | H | NH | CHMe | OEt |
1-85 | 0 | H | NH | CHMe | OCH 2Ph |
1-86 | 0 | H | NH | CHMe | NH 2 |
1-87 | 0 | H | NH | CHMe | NHEt |
1-88 | 0 | H | NH | CHMe | NHSO 2Me |
1-89 | 0 | H | NH | CHMe | NHSO 2NMe 2 |
1-90 | 0 | H | NH | CHMe | NHSO 2N(Me)(CHMe 2) |
1-91 | 0 | F | NH | CHMe | OH |
1-92 | 0 | F | NH | CHMe | OMe |
1-93 | 0 | F | NH | CHMe | OEt |
1-94 | 0 | F | NH | CHMe | OCH 2Ph |
1-95 | 0 | F | NH | CHMe | NH 2 |
1-96 | 0 | F | NH | CHMe | NHEt |
1-97 | 0 | F | NH | CHMe | NHSO 2Me |
1-98 | 0 | F | NH | CHMe | NHSO 2NMe 2 |
1-99 | 0 | F | NH | CHMe | NHSO 2N(Me)(CHMe 2) |
1-100 | 0 | Cl | NH | CHMe | OH |
1-101 | 0 | Cl | NH | CHMe | OMe |
1-102 | 0 | Cl | NH | CHMe | OEt |
1-103 | 0 | Cl | NH | CHMe | OCH 2Ph |
1-104 | 0 | Cl | NH | CHMe | NH 2 |
1-105 | 0 | Cl | NH | CHMe | NHEt |
1-106 | 0 | Cl | NH | CHMe | NHSO 2Me |
1-107 | 0 | Cl | NH | CHMe | NHSO 2NMe 2 |
1-108 | 0 | Cl | NH | CHMe | NHSO 2N(Me)(CHMe 2) |
1-109 | 0 | H | O | CHEt | OH |
1-110 | 0 | H | O | CHEt | OMe |
1-111 | 0 | H | O | CHEt | OEt |
1-112 | 0 | H | O | CHEt | OCH 2Ph |
1-113 | 0 | H | O | CHEt | NHSO 2Me |
1-114 | 0 | H | O | CHEt | NHSO 2N(Me)(CHMe 2) |
1-115 | 0 | F | O | CHEt | OH |
1-116 | 0 | F | O | CHEt | OMe |
1-117 | 0 | F | O | CHEt | OEt |
1-118 | 0 | F | O | CHEt | OCH 2Ph |
1-119 | 0 | F | O | CHEt | NHSO 2Me |
1-120 | 0 | F | O | CHEt | NHSO 2N(Me)(CHMe 2) |
1-121 | 0 | H | NH | CHEt | OH |
1-122 | 0 | H | NH | CHEt | OMe |
1-123 | 0 | H | NH | CHEt | OEt |
1-124 | 0 | H | NH | CHEt | OCH 2Ph |
1-125 | 0 | H | NH | CHEt | NHSO 2Me |
1-126 | 0 | H | NH | CHEt | NHSO 2N(Me)(CHMe 2) |
1-127 | 0 | F | NH | CHEt | OH |
1-128 | 0 | F | NH | CHEt | OMe |
1-129 | 0 | F | NH | CHEt | OEt |
1-130 | 0 | F | NH | CHEt | OCH 2Ph |
1-131 | 0 | F | NH | CHEt | NHSO 2Me |
1-132 | 0 | F | NH | CHEt | NHSO 2N(Me)(CHMe 2) |
1-133 | 0 | H | O | C(Me) 2 | OH |
1-134 | 0 | H | O | C(Me) 2 | OMe |
1-135 | 0 | H | O | C(Me) 2 | OEt |
1-136 | 0 | H | O | C(Me) 2 | OCH 2Ph |
1-137 | 0 | H | O | C(Me) 2 | NH 2 |
1-138 | 0 | H | O | C(Me) 2 | NHEt |
1-139 | 0 | H | O | C(Me) 2 | NHSO 2Me |
1-140 | 0 | H | O | C(Me) 2 | NHSO 2NMe 2 |
1-141 | 0 | H | O | C(Me) 2 | NHSO 2N(Me)(CHMe 2) |
1-142 | 0 | F | O | C(Me) 2 | OH |
1-143 | 0 | F | O | C(Me) 2 | OMe |
1-144 | 0 | F | O | C(Me) 2 | OEt |
1-145 | 0 | F | O | C(Me) 2 | OCH 2Ph |
1-146 | 0 | F | O | C(Me) 2 | NH 2 |
1-147 | 0 | F | O | C(Me) 2 | NHEt |
1-148 | 0 | F | O | C(Me) 2 | NHSO 2Me |
1-149 | 0 | F | O | C(Me) 2 | NHSO 2NMe 2 |
1-150 | 0 | F | O | C(Me) 2 | NHSO 2N(Me)(CHMe 2) |
1-151 | 0 | Cl | O | C(Me) 2 | OH |
1-152 | 0 | Cl | O | C(Me) 2 | OMe |
1-153 | 0 | Cl | O | C(Me) 2 | OEt |
1-154 | 0 | Cl | O | C(Me) 2 | OCH 2Ph |
1-155 | 0 | Cl | O | C(Me) 2 | NH 2 |
1-156 | 0 | Cl | O | C(Me) 2 | NHEt |
1-157 | 0 | Cl | O | C(Me) 2 | NHSO 2Me |
1-158 | 0 | Cl | O | C(Me) 2 | NHSO 2NMe 2 |
1-159 | 0 | Cl | O | C(Me) 2 | NHSO 2N(Me)(CHMe 2) |
1-160 | 0 | H | NH | C(Me) 2 | OH |
1-161 | 0 | H | NH | C(Me) 2 | OMe |
1-162 | 0 | H | NH | C(Me) 2 | OEt |
1-163 | 0 | H | NH | C(Me) 2 | OCH 2Ph |
1-164 | 0 | H | NH | C(Me) 2 | NH 2 |
1-165 | 0 | H | NH | C(Me) 2 | NHEt |
1-166 | 0 | H | NH | C(Me) 2 | NHSO 2Me |
1-167 | 0 | H | NH | C(Me) 2 | NHSO 2NMe 2 |
1-168 | 0 | H | NH | C(Me) 2 | NHSO 2N(Me)(CHMe 2) |
1-169 | 0 | F | NH | C(Me) 2 | OH |
1-170 | 0 | F | NH | C(Me) 2 | OMe |
1-171 | 0 | F | NH | C(Me) 2 | OEt |
1-172 | 0 | F | NH | C(Me) 2 | OCH 2Ph |
1-173 | 0 | F | NH | C(Me) 2 | NH 2 |
1-174 | 0 | F | NH | C(Me) 2 | NHEt |
1-175 | 0 | F | NH | C(Me) 2 | NHSO 2Me |
1-176 | 0 | F | NH | C(Me) 2 | NHSO 2NMe 2 |
1-177 | 0 | F | NH | C(Me) 2 | NHSO 2N(Me)(CHMe 2) |
1-178 | 0 | Cl | NH | C(Me) 2 | OH |
1-179 | 0 | Cl | NH | C(Me) 2 | OMe |
1-180 | 0 | Cl | NH | C(Me) 2 | OEt |
1-181 | 0 | Cl | NH | C(Me) 2 | OCH 2Ph |
1-182 | 0 | Cl | NH | C(Me) 2 | NH 2 |
1-183 | 0 | Cl | NH | C(Me) 2 | NHEt |
1-184 | 0 | Cl | NH | C(Me) 2 | NHSO 2Me |
1-185 | 0 | Cl | NH | C(Me) 2 | NHSO 2NMe 2 |
1-186 | 0 | Cl | NH | C(Me) 2 | NHSO 2N(Me)(CHMe 2) |
1-187 | 0 | H | O | C(CH 2CH 2) | OH |
1-188 | 0 | H | O | C(CH 2CH 2) | OMe |
1-189 | 0 | H | O | C(CH 2CH 2) | OEt |
1-190 | 0 | H | O | C(CH 2CH 2) | OCH 2Ph |
1-191 | 0 | H | O | C(CH 2CH 2) | NHSO 2Me |
1-192 | 0 | H | O | C(CH 2CH 2) | NHSO 2N(Me)(CHMe 2) |
1-193 | 0 | F | O | C(CH 2CH 2) | OH |
1-194 | 0 | F | O | C(CH 2CH 2) | OMe |
1-195 | 0 | F | O | C(CH 2CH 2) | OEt |
1-196 | 0 | F | O | C(CH 2CH 2) | OCH 2Ph |
1-197 | 0 | F | O | C(CH 2CH 2) | NHSO 2Me |
1-198 | 0 | F | O | C(CH 2CH 2) | NHSO 2N(Me)(CHMe 2) |
1-199 | 0 | H | NH | C(CH 2CH 2) | OH |
1-200 | 0 | H | NH | C(CH 2CH 2) | OMe |
1-201 | 0 | H | NH | C(CH 2CH 2) | OEt |
1-202 | 0 | H | NH | C(CH 2CH 2) | OCH 2Ph |
1-203 | 0 | H | NH | C(CH 2CH 2) | NHSO 2Me |
1-204 | 0 | H | NH | C(CH 2CH 2) | NHSO 2N(Me)(CHMe 2) |
1-205 | 0 | F | NH | C(CH 2CH 2) | OH |
1-206 | 0 | F | NH | C(CH 2CH 2) | OMe |
1-207 | 0 | F | NH | C(CH 2CH 2) | OEt |
1-208 | 0 | F | NH | C(CH 2CH 2) | OCH 2Ph |
1-209 | 0 | F | NH | C(CH 2CH 2) | NHSO 2Me |
1-210 | 0 | F | NH | C(CH 2CH 2) | NHSO 2N(Me)(CHMe 2) |
1-211 | 0 | H | O | C(CH 2CH 2OCH 2CH 2) | OH |
1-212 | 0 | H | O | C(CH 2CH 2OCH 2CH 2) | OMe |
1-213 | 0 | H | O | C(CH 2CH 2OCH 2CH 2) | OEt |
1-214 | 0 | H | O | C(CH 2CH 2OCH 2CH 2) | OCH 2Ph |
1-215 | 0 | H | O | C(CH 2CH 2OCH 2CH 2) | NHSO 2Me |
1-216 | 0 | H | O | C(CH 2CH 2OCH 2CH 2) | NHSO 2N(Me)(CHMe 2) |
1-217 | 0 | F | O | C(CH 2CH 2OCH 2CH 2) | OH |
1-218 | 0 | F | O | C(CH 2CH 2OCH 2CH 2) | OMe |
1-219 | 0 | F | O | C(CH 2CH 2OCH 2CH 2) | OEt |
1-220 | 0 | F | O | C(CH 2CH 2OCH 2CH 2) | OCH 2Ph |
1-221 | 0 | F | O | C(CH 2CH 2OCH 2CH 2) | NHSO 2Me |
1-222 | 0 | F | O | C(CH 2CH 2OCH 2CH 2) | NHSO 2N(Me)(CHMe 2) |
1-223 | 0 | H | NH | C(CH 2CH 2OCH 2CH 2) | OH |
1-224 | 0 | H | NH | C(CH 2CH 2OCH 2CH 2) | OMe |
1-225 | 0 | H | NH | C(CH 2CH 2OCH 2CH 2) | OEt |
1-226 | 0 | H | NH | C(CH 2CH 2OCH 2CH 2) | OCH 2Ph |
1-227 | 0 | H | NH | C(CH 2CH 2OCH 2CH 2) | NHSO 2Me |
1-228 | 0 | H | NH | C(CH 2CH 2OCH 2CH 2) | NHSO 2N(Me)(CHMe 2) |
1-229 | 0 | F | NH | C(CH 2CH 2OCH 2CH 2) | OH |
1-230 | 0 | F | NH | C(CH 2CH 2OCH 2CH 2) | OMe |
1-231 | 0 | F | NH | C(CH 2CH 2OCH 2CH 2) | OEt |
1-232 | 0 | F | NH | C(CH 2CH 2OCH 2CH 2) | OCH 2Ph |
1-233 | 0 | F | NH | C(CH 2CH 2OCH 2CH 2) | NHSO 2Me |
1-234 | 0 | F | NH | C(CH 2CH 2OCH 2CH 2) | NHSO 2N(Me)(CHMe 2) |
1-235 | 0 | H | O | CH 2CH 2 | OH |
1-236 | 0 | H | O | CH 2CH 2 | OMe |
1-237 | 0 | H | O | CH 2CH 2 | OEt |
1-238 | 0 | H | O | CH 2CH 2 | OCH 2Ph |
1-239 | 0 | H | O | CH 2CH 2 | NH 2 |
1-240 | 0 | H | O | CH 2CH 2 | NHEt |
1-241 | 0 | H | O | CH 2CH 2 | NHSO 2Me |
1-242 | 0 | H | O | CH 2CH 2 | NHSO 2NMe 2 |
1-243 | 0 | H | O | CH 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-244 | 0 | F | O | CH 2CH 2 | OH |
1-245 | 0 | F | O | CH 2CH 2 | OMe |
1-246 | 0 | F | O | CH 2CH 2 | OEt |
1-247 | 0 | F | O | CH 2CH 2 | OCH 2Ph |
1-248 | 0 | F | O | CH 2CH 2 | NH 2 |
1-249 | 0 | F | O | CH 2CH 2 | NHEt |
1-250 | 0 | F | O | CH 2CH 2 | NHSO 2Me |
1-251 | 0 | F | O | CH 2CH 2 | NHSO 2NMe 2 |
1-252 | 0 | F | O | CH 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-253 | 0 | Cl | O | CH 2CH 2 | OH |
1-254 | 0 | Cl | O | CH 2CH 2 | OMe |
1-255 | 0 | Cl | O | CH 2CH 2 | OEt |
1-256 | 0 | Cl | O | CH 2CH 2 | OCH 2Ph |
1-257 | 0 | Cl | O | CH 2CH 2 | NH 2 |
1-258 | 0 | Cl | O | CH 2CH 2 | NHEt |
1-259 | 0 | Cl | O | CH 2CH 2 | NHSO 2Me |
1-260 | 0 | Cl | O | CH 2CH 2 | NHSO 2NMe 2 |
1-261 | 0 | Cl | O | CH 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-262 | 0 | H | NH | CH 2CH 2 | OH |
1-263 | 0 | H | NH | CH 2CH 2 | OMe |
1-264 | 0 | H | NH | CH 2CH 2 | OEt |
1-265 | 0 | H | NH | CH 2CH 2 | OCH 2Ph |
1-266 | 0 | H | NH | CH 2CH 2 | NH 2 |
1-267 | 0 | H | NH | CH 2CH 2 | NHEt |
1-268 | 0 | H | NH | CH 2CH 2 | NHSO 2Me |
1-269 | 0 | H | NH | CH 2CH 2 | NHSO 2NMe 2 |
1-270 | 0 | H | NH | CH 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-271 | 0 | F | NH | CH 2CH 2 | OH |
1-272 | 0 | F | NH | CH 2CH 2 | OMe |
1-273 | 0 | F | NH | CH 2CH 2 | OEt |
1-274 | 0 | F | NH | CH 2CH 2 | OCH 2Ph |
1-275 | 0 | F | NH | CH 2CH 2 | NH 2 |
1-276 | 0 | F | NH | CH 2CH 2 | NHEt |
1-277 | 0 | F | NH | CH 2CH 2 | NHSO 2Me |
1-278 | 0 | F | NH | CH 2CH 2 | NHSO 2NMe 2 |
1-279 | 0 | F | NH | CH 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-280 | 0 | Cl | NH | CH 2CH 2 | OH |
1-281 | 0 | Cl | NH | CH 2CH 2 | OMe |
1-282 | 0 | Cl | NH | CH 2CH 2 | OEt |
1-283 | 0 | Cl | NH | CH 2CH 2 | OCH 2Ph |
1-284 | 0 | Cl | NH | CH 2CH 2 | NH 2 |
1-285 | 0 | Cl | NH | CH 2CH 2 | NHEt |
1-286 | 0 | Cl | NH | CH 2CH 2 | NHSO 2Me |
1-287 | 0 | Cl | NH | CH 2CH 2 | NHSO 2NMe 2 |
1-288 | 0 | Cl | NH | CH 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-289 | 0 | H | O | CHMeCH 2 | OH |
1-290 | 0 | H | O | CHMeCH 2 | OMe |
1-291 | 0 | H | O | CHMeCH 2 | OEt |
1-292 | 0 | H | O | CHMeCH 2 | OCH 2Ph |
1-293 | 0 | H | O | CHMeCH 2 | NH 2 |
1-294 | 0 | H | O | CHMeCH 2 | NHEt |
1-295 | 0 | H | O | CHMeCH 2 | NHSO 2Me |
1-296 | 0 | H | O | CHMeCH 2 | NHSO 2NMe 2 |
1-297 | 0 | H | O | CHMeCH 2 | NHSO 2N(Me)(CHMe 2) |
1-298 | 0 | F | O | CHMeCH 2 | OH |
1-299 | 0 | F | O | CHMeCH 2 | OMe |
1-300 | 0 | F | O | CHMeCH 2 | OEt |
1-301 | 0 | F | O | CHMeCH 2 | OCH 2Ph |
1-302 | 0 | F | O | CHMeCH 2 | NH 2 |
1-303 | 0 | F | O | CHMeCH 2 | NHEt |
1-304 | 0 | F | O | CHMeCH 2 | NHSO 2Me |
1-305 | 0 | F | O | CHMeCH 2 | NHSO 2NMe 2 |
1-306 | 0 | F | O | CHMeCH 2 | NHSO 2N(Me)(CHMe 2) |
1-307 | 0 | Cl | O | CHMeCH 2 | OH |
1-308 | 0 | Cl | O | CHMeCH 2 | OMe |
1-309 | 0 | Cl | O | CHMeCH 2 | OEt |
1-310 | 0 | Cl | O | CHMeCH 2 | OCH 2Ph |
1-311 | 0 | Cl | O | CHMeCH 2 | NH 2 |
1-312 | 0 | Cl | O | CHMeCH 2 | NHEt |
1-313 | 0 | Cl | O | CHMeCH 2 | NHSO 2Me |
1-314 | 0 | Cl | O | CHMeCH 2 | NHSO 2NMe 2 |
1-315 | 0 | Cl | O | CHMeCH 2 | NHSO 2N(Me)(CHMe 2) |
1-316 | 0 | H | NH | CHMeCH 2 | OH |
1-317 | 0 | H | NH | CHMeCH 2 | OMe |
1-318 | 0 | H | NH | CHMeCH 2 | OEt |
1-319 | 0 | H | NH | CHMeCH 2 | OCH 2Ph |
1-320 | 0 | H | NH | CHMeCH 2 | NH 2 |
1-321 | 0 | H | NH | CHMeCH 2 | NHEt |
1-322 | 0 | H | NH | CHMeCH 2 | NHSO 2Me |
1-323 | 0 | H | NH | CHMeCH 2 | NHSO 2NMe 2 |
1-324 | 0 | H | NH | CHMeCH 2 | NHSO 2N(Me)(CHMe 2) |
1-325 | 0 | F | NH | CHMeCH 2 | OH |
1-326 | 0 | F | NH | CHMeCH 2 | OMe |
1-327 | 0 | F | NH | CHMeCH 2 | OEt |
1-328 | 0 | F | NH | CHMeCH 2 | OCH 2Ph |
1-329 | 0 | F | NH | CHMeCH 2 | NH 2 |
1-330 | 0 | F | NH | CHMeCH 2 | NHEt |
1-331 | 0 | F | NH | CHMeCH 2 | NHSO 2Me |
1-332 | 0 | F | NH | CHMeCH 2 | NHSO 2NMe 2 |
1-333 | 0 | F | NH | CHMeCH 2 | NHSO 2N(Me)(CHMe 2) |
1-334 | 0 | Cl | NH | CHMeCH 2 | OH |
1-335 | 0 | Cl | NH | CHMeCH 2 | OMe |
1-336 | 0 | Cl | NH | CHMeCH 2 | OEt |
1-337 | 0 | Cl | NH | CHMeCH 2 | OCH 2Ph |
1-338 | 0 | Cl | NH | CHMeCH 2 | NH 2 |
1-339 | 0 | Cl | NH | CHMeCH 2 | NHEt |
1-340 | 0 | Cl | NH | CHMeCH 2 | NHSO 2Me |
1-341 | 0 | Cl | NH | CHMeCH 2 | NHSO 2NMe 2 |
1-342 | 0 | Cl | NH | CHMeCH 2 | NHSO 2N(Me)(CHMe 2) |
1-343 | 0 | H | O | CHEtCH 2 | OH |
1-344 | 0 | H | O | CHEtCH 2 | OMe |
1-345 | 0 | H | O | CHEtCH 2 | OEt |
1-346 | 0 | H | O | CHEtCH 2 | OCH 2Ph |
1-347 | 0 | H | O | CHEtCH 2 | NHSO 2Me |
1-348 | 0 | H | O | CHEtCH 2 | NHSO 2N(Me)(CHMe 2) |
1-349 | 0 | F | O | CHEtCH 2 | OH |
1-350 | 0 | F | O | CHEtCH 2 | OMe |
1-351 | 0 | F | O | CHEtCH 2 | OEt |
1-352 | 0 | F | O | CHEtCH 2 | OCH 2Ph |
1-353 | 0 | F | O | CHEtCH 2 | NHSO 2Me |
1-354 | 0 | F | O | CHEtCH 2 | NHSO 2N(Me)(CHMe 2) |
1-355 | 0 | H | NH | CHEtCH 2 | OH |
1-356 | 0 | H | NH | CHEtCH 2 | OMe |
1-357 | 0 | H | NH | CHEtCH 2 | OEt |
1-358 | 0 | H | NH | CHEtCH 2 | OCH 2Ph |
1-359 | 0 | H | NH | CHEtCH 2 | NHSO 2Me |
1-360 | 0 | H | NH | CHEtCH 2 | NHSO 2N(Me)(CHMe 2) |
1-361 | 0 | F | NH | CHEtCH 2 | OH |
1-362 | 0 | F | NH | CHEtCH 2 | OMe |
1-363 | 0 | F | NH | CHEtCH 2 | OEt |
1-364 | 0 | F | NH | CHEtCH 2 | OCH 2Ph |
1-365 | 0 | F | NH | CHEtCH 2 | NHSO 2Me |
1-366 | 0 | F | NH | CHEtCH 2 | NHSO 2N(Me)(CHMe 2) |
1-367 | 0 | H | O | CH 2CHMe | OH |
1-368 | 0 | H | O | CH 2CHMe | OMe |
1-369 | 0 | H | O | CH 2CHMe | OEt |
1-370 | 0 | H | O | CH 2CHMe | OCH 2Ph |
1-371 | 0 | H | O | CH 2CHMe | NH 2 |
1-372 | 0 | H | O | CH 2CHMe | NHEt |
1-373 | 0 | H | O | CH 2CHMe | NHSO 2Me |
1-374 | 0 | H | O | CH 2CHMe | NHSO 2NMe 2 |
1-375 | 0 | H | O | CH 2CHMe | NHSO 2N(Me)(CHMe 2) |
1-376 | 0 | F | O | CH 2CHMe | OH |
1-377 | 0 | F | O | CH 2CHMe | OMe |
1-378 | 0 | F | O | CH 2CHMe | OEt |
1-379 | 0 | F | O | CH 2CHMe | OCH 2Ph |
1-380 | 0 | F | O | CH 2CHMe | NH 2 |
1-381 | 0 | F | O | CH 2CHMe | NHEt |
1-382 | 0 | F | O | CH 2CHMe | NHSO 2Me |
1-383 | 0 | F | O | CH 2CHMe | NHSO 2NMe 2 |
1-384 | 0 | F | O | CH 2CHMe | NHSO 2N(Me)(CHMe 2) |
1-385 | 0 | Cl | O | CH 2CHMe | OH |
1-386 | 0 | Cl | O | CH 2CHMe | OMe |
1-387 | 0 | Cl | O | CH 2CHMe | OEt |
1-388 | 0 | Cl | O | CH 2CHMe | OCH 2Ph |
1-389 | 0 | Cl | O | CH 2CHMe | NH 2 |
1-390 | 0 | Cl | O | CH 2CHMe | NHEt |
1-391 | 0 | Cl | O | CH 2CHMe | NHSO 2Me |
1-392 | 0 | Cl | O | CH 2CHMe | NHSO 2NMe 2 |
1-393 | 0 | Cl | O | CH 2CHMe | NHSO 2N(Me)(CHMe 2) |
1-394 | 0 | H | NH | CH 2CHMe | OH |
1-395 | 0 | H | NH | CH 2CHMe | OMe |
1-396 | 0 | H | NH | CH 2CHMe | OEt |
1-397 | 0 | H | NH | CH 2CHMe | OCH 2Ph |
1-398 | 0 | H | NH | CH 2CHMe | NH 2 |
1-399 | 0 | H | NH | CH 2CHMe | NHEt |
1-400 | 0 | H | NH | CH 2CHMe | NHSO 2Me |
1-401 | 0 | H | NH | CH 2CHMe | NHSO 2NMe 2 |
1-402 | 0 | H | NH | CH 2CHMe | NHSO 2N(Me)(CHMe 2) |
1-403 | 0 | F | NH | CH 2CHMe | OH |
1-404 | 0 | F | NH | CH 2CHMe | OMe |
1-405 | 0 | F | NH | CH 2CHMe | OEt |
1-406 | 0 | F | NH | CH 2CHMe | OCH 2Ph |
1-407 | 0 | F | NH | CH 2CHMe | NH 2 |
1-408 | 0 | F | NH | CH 2CHMe | NHEt |
1-409 | 0 | F | NH | CH 2CHMe | NHSO 2Me |
1-410 | 0 | F | NH | CH 2CHMe | NHSO 2NMe 2 |
1-411 | 0 | F | NH | CH 2CHMe | NHSO 2N(Me)(CHMe 2) |
1-412 | 0 | Cl | NH | CH 2CHMe | OH |
1-413 | 0 | Cl | NH | CH 2CHMe | OMe |
1-414 | 0 | Cl | NH | CH 2CHMe | OEt |
1-415 | 0 | Cl | NH | CH 2CHMe | OCH 2Ph |
1-416 | 0 | Cl | NH | CH 2CHMe | NH 2 |
1-417 | 0 | Cl | NH | CH 2CHMe | NHEt |
1-418 | 0 | Cl | NH | CH 2CHMe | NHSO 2Me |
1-419 | 0 | Cl | NH | CH 2CHMe | NHSO 2NMe 2 |
1-420 | 0 | Cl | NH | CH 2CHMe | NHSO 2N(Me)(CHMe 2) |
1-421 | 0 | H | O | CHMeCHMe | OH |
1-422 | 0 | H | O | CHMeCHMe | OMe |
1-423 | 0 | H | O | CHMeCHMe | OEt |
1-424 | 0 | H | O | CHMeCHMe | OCH 2Ph |
1-425 | 0 | H | O | CHMeCHMe | NHSO 2Me |
1-426 | 0 | H | O | CHMeCHMe | NHSO 2N(Me)(CHMe 2) |
1-427 | 0 | F | O | CHMeCHMe | OH |
1-428 | 0 | F | O | CHMeCHMe | OMe |
1-429 | 0 | F | O | CHMeCHMe | OEt |
1-430 | 0 | F | O | CHMeCHMe | OCH 2Ph |
1-431 | 0 | F | O | CHMeCHMe | NHSO 2Me |
1-432 | 0 | F | O | CHMeCHMe | NHSO 2N(Me)(CHMe 2) |
1-433 | 0 | H | NH | CHMeCHMe | OH |
1-434 | 0 | H | NH | CHMeCHMe | OMe |
1-435 | 0 | H | NH | CHMeCHMe | OEt |
1-436 | 0 | H | NH | CHMeCHMe | OCH 2Ph |
1-437 | 0 | H | NH | CHMeCHMe | NHSO 2Me |
1-438 | 0 | H | NH | CHMeCHMe | NHSO 2N(Me)(CHMe 2) |
1-439 | 0 | F | NH | CHMeCHMe | OH |
1-440 | 0 | F | NH | CHMeCHMe | OMe |
1-441 | 0 | F | NH | CHMeCHMe | OEt |
1-442 | 0 | F | NH | CHMeCHMe | OCH 2Ph |
1-443 | 0 | F | NH | CHMeCHMe | NHSO 2Me |
1-444 | 0 | F | NH | CHMeCHMe | NHSO 2N(Me)(CHMe 2) |
1-445 | 0 | H | O | CMe 2CH 2 | OH |
1-446 | 0 | H | O | CMe 2CH 2 | OMe |
1-447 | 0 | H | O | CMe 2CH 2 | OEt |
1-448 | 0 | H | O | CMe 2CH 2 | OCH 2Ph |
1-449 | 0 | H | O | CMe 2CH 2 | NH 2 |
1-450 | 0 | H | O | CMe 2CH 2 | NHEt |
1-451 | 0 | H | O | CMe 2CH 2 | NHSO 2Me |
1-452 | 0 | H | O | CMe 2CH 2 | NHSO 2NMe 2 |
1-453 | 0 | H | O | CMe 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-454 | 0 | F | O | CMe 2CH 2 | OH |
1-455 | 0 | F | O | CMe 2CH 2 | OMe |
1-456 | 0 | F | O | CMe 2CH 2 | OEt |
1-457 | 0 | F | O | CMe 2CH 2 | OCH 2Ph |
1-458 | 0 | F | O | CMe 2CH 2 | NH 2 |
1-459 | 0 | F | O | CMe 2CH 2 | NHEt |
1-460 | 0 | F | O | CMe 2CH 2 | NHSO 2Me |
1-461 | 0 | F | O | CMe 2CH 2 | NHSO 2NMe 2 |
1-462 | 0 | F | O | CMe 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-463 | 0 | Cl | O | CMe 2CH 2 | OH |
1-464 | 0 | Cl | O | CMe 2CH 2 | OMe |
1-465 | 0 | Cl | O | CMe 2CH 2 | OEt |
1-466 | 0 | Cl | O | CMe 2CH 2 | OCH 2Ph |
1-467 | 0 | Cl | O | CMe 2CH 2 | NH 2 |
1-468 | 0 | Cl | O | CMe 2CH 2 | NHEt |
1-469 | 0 | Cl | O | CMe 2CH 2 | NHSO 2Me |
1-470 | 0 | Cl | O | CMe 2CH 2 | NHSO 2NMe 2 |
1-471 | 0 | Cl | O | CMe 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-472 | 0 | H | NH | CMe 2CH 2 | OH |
1-473 | 0 | H | NH | CMe 2CH 2 | OMe |
1-474 | 0 | H | NH | CMe 2CH 2 | OEt |
1-475 | 0 | H | NH | CMe 2CH 2 | OCH 2Ph |
1-476 | 0 | H | NH | CMe 2CH 2 | NH 2 |
1-477 | 0 | H | NH | CMe 2CH 2 | NHEt |
1-478 | 0 | H | NH | CMe 2CH 2 | NHSO 2Me |
1-479 | 0 | H | NH | CMe 2CH 2 | NHSO 2NMe 2 |
1-480 | 0 | H | NH | CMe 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-481 | 0 | F | NH | CMe 2CH 2 | OH |
1-482 | 0 | F | NH | CMe 2CH 2 | OMe |
1-483 | 0 | F | NH | CMe 2CH 2 | OEt |
1-484 | 0 | F | NH | CMe 2CH 2 | OCH 2Ph |
1-485 | 0 | F | NH | CMe 2CH 2 | NH 2 |
1-486 | 0 | F | NH | CMe 2CH 2 | NHEt |
1-487 | 0 | F | NH | CMe 2CH 2 | NHSO 2Me |
1-488 | 0 | F | NH | CMe 2CH 2 | NHSO 2NMe 2 |
1-489 | 0 | F | NH | CMe 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-490 | 0 | Cl | NH | CMe 2CH 2 | OH |
1-491 | 0 | Cl | NH | CMe 2CH 2 | OMe |
1-492 | 0 | Cl | NH | CMe 2CH 2 | OEt |
1-493 | 0 | Cl | NH | CMe 2CH 2 | OCH 2Ph |
1-494 | 0 | Cl | NH | CMe 2CH 2 | NH 2 |
1-495 | 0 | Cl | NH | CMe 2CH 2 | NHEt |
1-496 | 0 | Cl | NH | CMe 2CH 2 | NHSO 2Me |
1-497 | 0 | Cl | NH | CMe 2CH 2 | NHSO 2NMe 2 |
1-498 | 0 | Cl | NH | CMe 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-499 | 0 | H | O | CH 2CMe 2 | OH |
1-500 | 0 | H | O | CH 2CMe 2 | OMe |
1-501 | 0 | H | O | CH 2CMe 2 | OEt |
1-502 | 0 | H | O | CH 2CMe 2 | OCH 2Ph |
1-503 | 0 | H | O | CH 2CMe 2 | NH 2 |
1-504 | 0 | H | O | CH 2CMe 2 | NHEt |
1-505 | 0 | H | O | CH 2CMe 2 | NHSO 2Me |
1-506 | 0 | H | O | CH 2CMe 2 | NHSO 2NMe 2 |
1-507 | 0 | H | O | CH 2CMe 2 | NHSO 2N(Me)(CHMe 2) |
1-508 | 0 | F | O | CH 2CMe 2 | OH |
1-509 | 0 | F | O | CH 2CMe 2 | OMe |
1-510 | 0 | F | O | CH 2CMe 2 | OEt |
1-511 | 0 | F | O | CH 2CMe 2 | OCH 2Ph |
1-512 | 0 | F | O | CH 2CMe 2 | NH 2 |
1-513 | 0 | F | O | CH 2CMe 2 | NHEt |
1-514 | 0 | F | O | CH 2CMe 2 | NHSO 2Me |
1-515 | 0 | F | O | CH 2CMe 2 | NHSO 2NMe 2 |
1-516 | 0 | F | O | CH 2CMe 2 | NHSO 2N(Me)(CHMe 2) |
1-517 | 0 | Cl | O | CH 2CMe 2 | OH |
1-518 | 0 | Cl | O | CH 2CMe 2 | OMe |
1-519 | 0 | Cl | O | CH 2CMe 2 | OEt |
1-520 | 0 | Cl | O | CH 2CMe 2 | OCH 2Ph |
1-521 | 0 | Cl | O | CH 2CMe 2 | NH 2 |
1-522 | 0 | Cl | O | CH 2CMe 2 | NHEt |
1-523 | 0 | Cl | O | CH 2CMe 2 | NHSO 2Me |
1-524 | 0 | Cl | O | CH 2CMe 2 | NHSO 2NMe 2 |
1-525 | 0 | Cl | O | CH 2CMe 2 | NHSO 2N(Me)(CHMe 2) |
1-526 | 0 | H | NH | CH 2CMe 2 | OH |
1-527 | 0 | H | NH | CH 2CMe 2 | OMe |
1-528 | 0 | H | NH | CH 2CMe 2 | OEt |
1-529 | 0 | H | NH | CH 2CMe 2 | OCH 2Ph |
1-530 | 0 | H | NH | CH 2CMe 2 | NH 2 |
1-531 | 0 | H | NH | CH 2CMe 2 | NHEt |
1-532 | 0 | H | NH | CH 2CMe 2 | NHSO 2Me |
1-533 | 0 | H | NH | CH 2CMe 2 | NHSO 2NMe 2 |
1-534 | 0 | H | NH | CH 2CMe 2 | NHSO 2N(Me)(CHMe 2) |
1-535 | 0 | F | NH | CH 2CMe 2 | OH |
1-536 | 0 | F | NH | CH 2CMe 2 | OMe |
1-537 | 0 | F | NH | CH 2CMe 2 | OEt |
1-538 | 0 | F | NH | CH 2CMe 2 | OCH 2Ph |
1-539 | 0 | F | NH | CH 2CMe 2 | NH 2 |
1-540 | 0 | F | NH | CH 2CMe 2 | NHEt |
1-541 | 0 | F | NH | CH 2CMe 2 | NHSO 2Me |
1-542 | 0 | F | NH | CH 2CMe 2 | NHSO 2NMe 2 |
1-543 | 0 | F | NH | CH 2CMe 2 | NHSO 2N(Me)(CHMe 2) |
1-544 | 0 | Cl | NH | CH 2CMe 2 | OH |
1-545 | 0 | Cl | NH | CH 2CMe 2 | OMe |
1-546 | 0 | Cl | NH | CH 2CMe 2 | OEt |
1-547 | 0 | Cl | NH | CH 2CMe 2 | OCH 2Ph |
1-548 | 0 | Cl | NH | CH 2CMe 2 | NH 2 |
1-549 | 0 | Cl | NH | CH 2CMe 2 | NHEt |
1-550 | 0 | Cl | NH | CH 2CMe 2 | NHSO 2Me |
1-551 | 0 | Cl | NH | CH 2CMe 2 | NHSO 2NMe 2 |
1-552 | 0 | Cl | NH | CH 2CMe 2 | NHSO 2N(Me)(CHMe 2) |
1-553 | 0 | H | O | CH 2CHCl | OH |
1-554 | 0 | H | O | CH 2CHCl | OMe |
1-555 | 0 | H | O | CH 2CHCl | OEt |
1-556 | 0 | H | O | CH 2CHCl | OCH 2Ph |
1-557 | 0 | H | O | CH 2CHCl | NHSO 2Me |
1-558 | 0 | H | O | CH 2CHCl | NHSO 2N(Me)(CHMe 2) |
1-559 | 0 | F | O | CH 2CHCl | OH |
1-560 | 0 | F | O | CH 2CHCl | OMe |
1-561 | 0 | F | O | CH 2CHCl | OEt |
1-562 | 0 | F | O | CH 2CHCl | OCH 2Ph |
1-563 | 0 | F | O | CH 2CHCl | NHSO 2Me |
1-564 | 0 | F | O | CH 2CHCl | NHSO 2N(Me)(CHMe 2) |
1-565 | 0 | H | NH | CH 2CHCl | OH |
1-566 | 0 | H | NH | CH 2CHCl | OMe |
1-567 | 0 | H | NH | CH 2CHCl | OEt |
1-568 | 0 | H | NH | CH 2CHCl | OCH 2Ph |
1-569 | 0 | H | NH | CH 2CHCl | NHSO 2Me |
1-570 | 0 | H | NH | CH 2CHCl | NHSO 2N(Me)(CHMe 2) |
1-571 | 0 | F | NH | CH 2CHCl | OH |
1-572 | 0 | F | NH | CH 2CHCl | OMe |
1-573 | 0 | F | NH | CH 2CHCl | OEt |
1-574 | 0 | F | NH | CH 2CHCl | OCH 2Ph |
1-575 | 0 | F | NH | CH 2CHCl | NHSO 2Me |
1-576 | 0 | F | NH | CH 2CHCl | NHSO 2N(Me)(CHMe 2) |
1-577 | 0 | H | O | C(CH 2CH 2)CH 2 | OH |
1-578 | 0 | H | O | C(CH 2CH 2)CH 2 | OMe |
1-579 | 0 | H | O | C(CH 2CH 2)CH 2 | OEt |
1-580 | 0 | H | O | C(CH 2CH 2)CH 2 | OCH 2Ph |
1-581 | 0 | H | O | C(CH 2CH 2)CH 2 | NHSO 2Me |
1-582 | 0 | H | O | C(CH 2CH 2)CH 2 | NHSO 2N(Me)(CHMe 2) |
1-583 | 0 | F | O | C(CH 2CH 2)CH 2 | OH |
1-584 | 0 | F | O | C(CH 2CH 2)CH 2 | OMe |
1-585 | 0 | F | O | C(CH 2CH 2)CH 2 | OEt |
1-586 | 0 | F | O | C(CH 2CH 2)CH 2 | OCH 2Ph |
1-587 | 0 | F | O | C(CH 2CH 2)CH 2 | NHSO 2Me |
1-588 | 0 | F | O | C(CH 2CH 2)CH 2 | NHSO 2N(Me)(CHMe 2) |
1-589 | 0 | H | NH | C(CH 2CH 2)CH 2 | OH |
1-590 | 0 | H | NH | C(CH 2CH 2)CH 2 | OMe |
1-591 | 0 | H | NH | C(CH 2CH 2)CH 2 | OEt |
1-592 | 0 | H | NH | C(CH 2CH 2)CH 2 | OCH 2Ph |
1-593 | 0 | H | NH | C(CH 2CH 2)CH 2 | NHSO 2Me |
1-594 | 0 | H | NH | C(CH 2CH 2)CH 2 | NHSO 2N(Me)(CHMe 2) |
1-595 | 0 | F | NH | C(CH 2CH 2)CH 2 | OH |
1-596 | 0 | F | NH | C(CH 2CH 2)CH 2 | OMe |
1-597 | 0 | F | NH | C(CH 2CH 2)CH 2 | OEt |
1-598 | 0 | F | NH | C(CH 2CH 2)CH 2 | OCH 2Ph |
1-599 | 0 | F | NH | C(CH 2CH 2)CH 2 | NHSO 2Me |
1-600 | 0 | F | NH | C(CH 2CH 2)CH 2 | NHSO 2N(Me)(CHMe 2) |
1-601 | 0 | H | O | CH 2C(CH 2CH 2) | OH |
1-602 | 0 | H | O | CH 2C(CH 2CH 2) | OMe |
1-603 | 0 | H | O | CH 2C(CH 2CH 2) | OEt |
1-604 | 0 | H | O | CH 2C(CH 2CH 2) | OCH 2Ph |
1-605 | 0 | H | O | CH 2C(CH 2CH 2) | NHSO 2Me |
1-606 | 0 | H | O | CH 2C(CH 2CH 2) | NHSO 2N(Me)(CHMe 2) |
1-607 | 0 | F | O | CH 2C(CH 2CH 2) | OH |
1-608 | 0 | F | O | CH 2C(CH 2CH 2) | OMe |
1-609 | 0 | F | O | CH 2C(CH 2CH 2) | OEt |
1-610 | 0 | F | O | CH 2C(CH 2CH 2) | OCH 2Ph |
1-611 | 0 | F | O | CH 2C(CH 2CH 2) | NHSO 2Me |
1-612 | 0 | F | O | CH 2C(CH 2CH 2) | NHSO 2N(Me)(CHMe 2) |
1-613 | 0 | H | NH | CH 2C(CH 2CH 2) | OH |
1-614 | 0 | H | NH | CH 2C(CH 2CH 2) | OMe |
1-615 | 0 | H | NH | CH 2C(CH 2CH 2) | OEt |
1-616 | 0 | H | NH | CH 2C(CH 2CH 2) | OCH 2Ph |
1-617 | 0 | H | NH | CH 2C(CH 2CH 2) | NHSO 2Me |
1-618 | 0 | H | NH | CH 2C(CH 2CH 2) | NHSO 2N(Me)(CHMe 2) |
1-619 | 0 | F | NH | CH 2C(CH 2CH 2) | OH |
1-620 | 0 | F | NH | CH 2C(CH 2CH 2) | OMe |
1-621 | 0 | F | NH | CH 2C(CH 2CH 2) | OEt |
1-622 | 0 | F | NH | CH 2C(CH 2CH 2) | OCH 2Ph |
1-623 | 0 | F | NH | CH 2C(CH 2CH 2) | NHSO 2Me |
1-624 | 0 | F | NH | CH 2C(CH 2CH 2) | NHSO 2N(Me)(CHMe 2) |
1-625 | 0 | H | O | CH(CH 2)CH | OH |
1-626 | 0 | H | O | CH(CH 2)CH | OMe |
1-627 | 0 | H | O | CH(CH 2)CH | OEt |
1-628 | 0 | H | O | CH(CH 2)CH | OCH 2Ph |
1-629 | 0 | H | O | CH(CH 2)CH | NHSO 2Me |
1-630 | 0 | H | O | CH(CH 2)CH | NHSO 2N(Me)(CHMe 2) |
1-631 | 0 | F | O | CH(CH 2)CH | OH |
1-632 | 0 | F | O | CH(CH 2)CH | OMe |
1-633 | 0 | F | O | CH(CH 2)CH | OEt |
1-634 | 0 | F | O | CH(CH 2)CH | OCH 2Ph |
1-635 | 0 | F | O | CH(CH 2)CH | NHSO 2Me |
1-636 | 0 | F | O | CH(CH 2)CH | NHSO 2N(Me)(CHMe 2) |
1-637 | 0 | H | NH | CH(CH 2)CH | OH |
1-638 | 0 | H | NH | CH(CH 2)CH | OMe |
1-639 | 0 | H | NH | CH(CH 2)CH | OEt |
1-640 | 0 | H | NH | CH(CH 2)CH | OCH 2Ph |
1-641 | 0 | H | NH | CH(CH 2)CH | NHSO 2Me |
1-642 | 0 | H | NH | CH(CH 2)CH | NHSO 2N(Me)(CHMe 2) |
1-643 | 0 | F | NH | CH(CH 2)CH | OH |
1-644 | 0 | F | NH | CH(CH 2)CH | OMe |
1-645 | 0 | F | NH | CH(CH 2)CH | OEt |
1-646 | 0 | F | NH | CH(CH 2)CH | OCH 2Ph |
1-647 | 0 | F | NH | CH(CH 2)CH | NHSO 2Me |
1-648 | 0 | F | NH | CH(CH 2)CH | NHSO 2N(Me)(CHMe 2) |
1-649 | 0 | H | O | CH 2CH 2CH 2 | OH |
1-650 | 0 | H | O | CH 2CH 2CH 2 | OMe |
1-651 | 0 | H | O | CH 2CH 2CH 2 | OEt |
1-652 | 0 | H | O | CH 2CH 2CH 2 | OCH 2Ph |
1-653 | 0 | H | O | CH 2CH 2CH 2 | NH 2 |
1-654 | 0 | H | O | CH 2CH 2CH 2 | NHEt |
1-655 | 0 | H | O | CH 2CH 2CH 2 | NHSO 2Me |
1-656 | 0 | H | O | CH 2CH 2CH 2 | NHSO 2NMe 2 |
1-657 | 0 | H | O | CH 2CH 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-658 | 0 | F | O | CH 2CH 2CH 2 | OH |
1-659 | 0 | F | O | CH 2CH 2CH 2 | OMe |
1-660 | 0 | F | O | CH 2CH 2CH 2 | OEt |
1-661 | 0 | F | O | CH 2CH 2CH 2 | OCH 2Ph |
1-662 | 0 | F | O | CH 2CH 2CH 2 | NH 2 |
1-663 | 0 | F | O | CH 2CH 2CH 2 | NHEt |
1-664 | 0 | F | O | CH 2CH 2CH 2 | NHSO 2Me |
1-665 | 0 | F | O | CH 2CH 2CH 2 | NHSO 2NMe 2 |
1-666 | 0 | F | O | CH 2CH 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-667 | 0 | Cl | O | CH 2CH 2CH 2 | OH |
1-668 | 0 | Cl | O | CH 2CH 2CH 2 | OMe |
1-669 | 0 | Cl | O | CH 2CH 2CH 2 | OEt |
1-670 | 0 | Cl | O | CH 2CH 2CH 2 | OCH 2Ph |
1-671 | 0 | Cl | O | CH 2CH 2CH 2 | NH 2 |
1-672 | 0 | Cl | O | CH 2CH 2CH 2 | NHEt |
1-673 | 0 | Cl | O | CH 2CH 2CH 2 | NHSO 2Me |
1-674 | 0 | Cl | O | CH 2CH 2CH 2 | NHSO 2NMe 2 |
1-675 | 0 | Cl | O | CH 2CH 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-676 | 0 | H | NH | CH 2CH 2CH 2 | OH |
1-677 | 0 | H | NH | CH 2CH 2CH 2 | OMe |
1-678 | 0 | H | NH | CH 2CH 2CH 2 | OEt |
1-679 | 0 | H | NH | CH 2CH 2CH 2 | OCH 2Ph |
1-680 | 0 | H | NH | CH 2CH 2CH 2 | NH 2 |
1-681 | 0 | H | NH | CH 2CH 2CH 2 | NHEt |
1-682 | 0 | H | NH | CH 2CH 2CH 2 | NHSO 2Me |
1-683 | 0 | H | NH | CH 2CH 2CH 2 | NHSO 2NMe 2 |
1-684 | 0 | H | NH | CH 2CH 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-685 | 0 | F | NH | CH 2CH 2CH 2 | OH |
1-686 | 0 | F | NH | CH 2CH 2CH 2 | OMe |
1-687 | 0 | F | NH | CH 2CH 2CH 2 | OEt |
1-688 | 0 | F | NH | CH 2CH 2CH 2 | OCH 2Ph |
1-689 | 0 | F | NH | CH 2CH 2CH 2 | NH 2 |
1-690 | 0 | F | NH | CH 2CH 2CH 2 | NHEt |
1-691 | 0 | F | NH | CH 2CH 2CH 2 | NHSO 2Me |
1-692 | 0 | F | NH | CH 2CH 2CH 2 | NHSO 2NMe 2 |
1-693 | 0 | F | NH | CH 2CH 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-694 | 0 | Cl | NH | CH 2CH 2CH 2 | OH |
1-695 | 0 | Cl | NH | CH 2CH 2CH 2 | OMe |
1-696 | 0 | Cl | NH | CH 2CH 2CH 2 | OEt |
1-697 | 0 | Cl | NH | CH 2CH 2CH 2 | OCH 2Ph |
1-698 | 0 | Cl | NH | CH 2CH 2CH 2 | NH 2 |
1-699 | 0 | Cl | NH | CH 2CH 2CH 2 | NHEt |
1-700 | 0 | Cl | NH | CH 2CH 2CH 2 | NHSO 2Me |
1-701 | 0 | Cl | NH | CH 2CH 2CH 2 | NHSO 2NMe 2 |
1-702 | 0 | Cl | NH | CH 2CH 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-703 | 0 | H | O | CHMeCH 2CH 2 | OH |
1-704 | 0 | H | O | CHMeCH 2CH 2 | OMe |
1-705 | 0 | H | O | CHMeCH 2CH 2 | OEt |
1-706 | 0 | H | O | CHMeCH 2CH 2 | OCH 2Ph |
1-707 | 0 | H | O | CHMeCH 2CH 2 | NHSO 2Me |
1-708 | 0 | H | O | CHMeCH 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-709 | 0 | F | O | CHMeCH 2CH 2 | OH |
1-710 | 0 | F | O | CHMeCH 2CH 2 | OMe |
1-711 | 0 | F | O | CHMeCH 2CH 2 | OEt |
1-712 | 0 | F | O | CHMeCH 2CH 2 | OCH 2Ph |
1-713 | 0 | F | O | CHMeCH 2CH 2 | NHSO 2Me |
1-714 | 0 | F | O | CHMeCH 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-715 | 0 | H | NH | CHMeCH 2CH 2 | OH |
1-716 | 0 | H | NH | CHMeCH 2CH 2 | OMe |
1-717 | 0 | H | NH | CHMeCH 2CH 2 | OEt |
1-718 | 0 | H | NH | CHMeCH 2CH 2 | OCH 2Ph |
1-719 | 0 | H | NH | CHMeCH 2CH 2 | NHSO 2Me |
1-720 | 0 | H | NH | CHMeCH 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-721 | 0 | F | NH | CHMeCH 2CH 2 | OH |
1-722 | 0 | F | NH | CHMeCH 2CH 2 | OMe |
1-723 | 0 | F | NH | CHMeCH 2CH 2 | OEt |
1-724 | 0 | F | NH | CHMeCH 2CH 2 | OCH 2Ph |
1-725 | 0 | F | NH | CHMeCH 2CH 2 | NHSO 2Me |
1-726 | 0 | F | NH | CHMeCH 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-727 | 0 | H | O | 1,3-環丁基 | OH |
1-728 | 0 | H | O | 1,3-環丁基 | OMe |
1-729 | 0 | H | O | 1,3-環丁基 | OEt |
1-730 | 0 | H | O | 1,3-環丁基 | OCH 2Ph |
1-731 | 0 | H | O | 1,3-環丁基 | NHSO 2Me |
1-732 | 0 | H | O | 1,3-環丁基 | NHSO 2N(Me)(CHMe 2) |
1-733 | 0 | F | O | 1,3-環丁基 | OH |
1-734 | 0 | F | O | 1,3-環丁基 | OMe |
1-735 | 0 | F | O | 1,3-環丁基 | OEt |
1-736 | 0 | F | O | 1,3-環丁基 | OCH 2Ph |
1-737 | 0 | F | O | 1,3-環丁基 | NHSO 2Me |
1-738 | 0 | F | O | 1,3-環丁基 | NHSO 2N(Me)(CHMe 2) |
1-739 | 0 | H | NH | 1,3-環丁基 | OH |
1-740 | 0 | H | NH | 1,3-環丁基 | OMe |
1-741 | 0 | H | NH | 1,3-環丁基 | OEt |
1-742 | 0 | H | NH | 1,3-環丁基 | OCH 2Ph |
1-743 | 0 | H | NH | 1,3-環丁基 | NHSO 2Me |
1-744 | 0 | H | NH | 1,3-環丁基 | NHSO 2N(Me)(CHMe 2) |
1-745 | 0 | F | NH | 1,3-環丁基 | OH |
1-746 | 0 | F | NH | 1,3-環丁基 | OMe |
1-747 | 0 | F | NH | 1,3-環丁基 | OEt |
1-748 | 0 | F | NH | 1,3-環丁基 | OCH 2Ph |
1-749 | 0 | F | NH | 1,3-環丁基 | NHSO 2Me |
1-750 | 0 | F | NH | 1,3-環丁基 | NHSO 2N(Me)(CHMe 2) |
1-751 | 0 | H | O | CH 2CH 2CH 2CH 2 | OH |
1-752 | 0 | H | O | CH 2CH 2CH 2CH 2 | OMe |
1-753 | 0 | H | O | CH 2CH 2CH 2CH 2 | OEt |
1-754 | 0 | H | O | CH 2CH 2CH 2CH 2 | OCH 2Ph |
1-755 | 0 | H | O | CH 2CH 2CH 2CH 2 | NHSO 2Me |
1-756 | 0 | H | O | CH 2CH 2CH 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-757 | 0 | F | O | CH 2CH 2CH 2CH 2 | OH |
1-758 | 0 | F | O | CH 2CH 2CH 2CH 2 | OMe |
1-759 | 0 | F | O | CH 2CH 2CH 2CH 2 | OEt |
1-760 | 0 | F | O | CH 2CH 2CH 2CH 2 | OCH 2Ph |
1-761 | 0 | F | O | CH 2CH 2CH 2CH 2 | NHSO 2Me |
1-762 | 0 | F | O | CH 2CH 2CH 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-763 | 0 | H | NH | CH 2CH 2CH 2CH 2 | OH |
1-764 | 0 | H | NH | CH 2CH 2CH 2CH 2 | OMe |
1-765 | 0 | H | NH | CH 2CH 2CH 2CH 2 | OEt |
1-766 | 0 | H | NH | CH 2CH 2CH 2CH 2 | OCH 2Ph |
1-767 | 0 | H | NH | CH 2CH 2CH 2CH 2 | NHSO 2Me |
1-768 | 0 | H | NH | CH 2CH 2CH 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-769 | 0 | F | NH | CH 2CH 2CH 2CH 2 | OH |
1-770 | 0 | F | NH | CH 2CH 2CH 2CH 2 | OMe |
1-771 | 0 | F | NH | CH 2CH 2CH 2CH 2 | OEt |
1-772 | 0 | F | NH | CH 2CH 2CH 2CH 2 | OCH 2Ph |
1-773 | 0 | F | NH | CH 2CH 2CH 2CH 2 | NHSO 2Me |
1-774 | 0 | F | NH | CH 2CH 2CH 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-775 | 0 | H | O | CHMeCH 2CH 2CH 2 | OH |
1-776 | 0 | H | O | CHMeCH 2CH 2CH 2 | OMe |
1-777 | 0 | H | O | CHMeCH 2CH 2CH 2 | OEt |
1-778 | 0 | H | O | CHMeCH 2CH 2CH 2 | OCH 2Ph |
1-779 | 0 | H | O | CHMeCH 2CH 2CH 2 | NHSO 2Me |
1-780 | 0 | H | O | CHMeCH 2CH 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-781 | 0 | F | O | CHMeCH 2CH 2CH 2 | OH |
1-782 | 0 | F | O | CHMeCH 2CH 2CH 2 | OMe |
1-783 | 0 | F | O | CHMeCH 2CH 2CH 2 | OEt |
1-784 | 0 | F | O | CHMeCH 2CH 2CH 2 | OCH 2Ph |
1-785 | 0 | F | O | CHMeCH 2CH 2CH 2 | NHSO 2Me |
1-786 | 0 | F | O | CHMeCH 2CH 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-787 | 0 | H | NH | CHMeCH 2CH 2CH 2 | OH |
1-788 | 0 | H | NH | CHMeCH 2CH 2CH 2 | OMe |
1-789 | 0 | H | NH | CHMeCH 2CH 2CH 2 | OEt |
1-790 | 0 | H | NH | CHMeCH 2CH 2CH 2 | OCH 2Ph |
1-791 | 0 | H | NH | CHMeCH 2CH 2CH 2 | NHSO 2Me |
1-792 | 0 | H | NH | CHMeCH 2CH 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-793 | 0 | F | NH | CHMeCH 2CH 2CH 2 | OH |
1-794 | 0 | F | NH | CHMeCH 2CH 2CH 2 | OMe |
1-795 | 0 | F | NH | CHMeCH 2CH 2CH 2 | OEt |
1-796 | 0 | F | NH | CHMeCH 2CH 2CH 2 | OCH 2Ph |
1-797 | 0 | F | NH | CHMeCH 2CH 2CH 2 | NHSO 2Me |
1-798 | 0 | F | NH | CHMeCH 2CH 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-799 | 1 | H | O | CH 2 | OH |
1-800 | 1 | H | O | CH 2 | OMe |
1-801 | 1 | H | O | CH 2 | OEt |
1-802 | 1 | H | O | CH 2 | OCH 2Ph |
1-803 | 1 | H | O | CH 2 | NHSO 2Me |
1-804 | 1 | H | O | CH 2 | NHSO 2N(Me)(CHMe 2) |
1-805 | 1 | F | O | CH 2 | OH |
1-806 | 1 | F | O | CH 2 | OMe |
1-807 | 1 | F | O | CH 2 | OEt |
1-808 | 1 | F | O | CH 2 | OCH 2Ph |
1-809 | 1 | F | O | CH 2 | NHSO 2Me |
1-810 | 1 | F | O | CH 2 | NHSO 2N(Me)(CHMe 2) |
1-811 | 1 | H | NH | CH 2 | OH |
1-812 | 1 | H | NH | CH 2 | OMe |
1-813 | 1 | H | NH | CH 2 | OEt |
1-814 | 1 | H | NH | CH 2 | OCH 2Ph |
1-815 | 1 | H | NH | CH 2 | NHSO 2Me |
1-816 | 1 | H | NH | CH 2 | NHSO 2N(Me)(CHMe 2) |
1-817 | 1 | F | NH | CH 2 | OH |
1-818 | 1 | F | NH | CH 2 | OMe |
1-819 | 1 | F | NH | CH 2 | OEt |
1-820 | 1 | F | NH | CH 2 | OCH 2Ph |
1-821 | 1 | F | NH | CH 2 | NHSO 2Me |
1-822 | 1 | F | NH | CH 2 | NHSO 2N(Me)(CHMe 2) |
1-823 | 1 | H | O | CHMe | OH |
1-824 | 1 | H | O | CHMe | OMe |
1-825 | 1 | H | O | CHMe | OEt |
1-826 | 1 | H | O | CHMe | OCH 2Ph |
1-827 | 1 | H | O | CHMe | NHSO 2Me |
1-828 | 1 | H | O | CHMe | NHSO 2N(Me)(CHMe 2) |
1-829 | 1 | F | O | CHMe | OH |
1-830 | 1 | F | O | CHMe | OMe |
1-831 | 1 | F | O | CHMe | OEt |
1-832 | 1 | F | O | CHMe | OCH 2Ph |
1-833 | 1 | F | O | CHMe | NHSO 2Me |
1-834 | 1 | F | O | CHMe | NHSO 2N(Me)(CHMe 2) |
1-835 | 1 | H | NH | CHMe | OH |
1-836 | 1 | H | NH | CHMe | OMe |
1-837 | 1 | H | NH | CHMe | OEt |
1-838 | 1 | H | NH | CHMe | OCH 2Ph |
1-839 | 1 | H | NH | CHMe | NHSO 2Me |
1-840 | 1 | H | NH | CHMe | NHSO 2N(Me)(CHMe 2) |
1-841 | 1 | F | NH | CHMe | OH |
1-842 | 1 | F | NH | CHMe | OMe |
1-843 | 1 | F | NH | CHMe | OEt |
1-844 | 1 | F | NH | CHMe | OCH 2Ph |
1-845 | 1 | F | NH | CHMe | NHSO 2Me |
1-846 | 1 | F | NH | CHMe | NHSO 2N(Me)(CHMe 2) |
1-847 | 1 | H | O | C(Me) 2 | OH |
1-848 | 1 | H | O | C(Me) 2 | OMe |
1-849 | 1 | H | O | C(Me) 2 | OEt |
1-850 | 1 | H | O | C(Me) 2 | OCH 2Ph |
1-851 | 1 | H | O | C(Me) 2 | NHSO 2Me |
1-852 | 1 | H | O | C(Me) 2 | NHSO 2N(Me)(CHMe 2) |
1-853 | 1 | F | O | C(Me) 2 | OH |
1-854 | 1 | F | O | C(Me) 2 | OMe |
1-855 | 1 | F | O | C(Me) 2 | OEt |
1-856 | 1 | F | O | C(Me) 2 | OCH 2Ph |
1-857 | 1 | F | O | C(Me) 2 | NHSO 2Me |
1-858 | 1 | F | O | C(Me) 2 | NHSO 2N(Me)(CHMe 2) |
1-859 | 1 | H | NH | C(Me) 2 | OH |
1-860 | 1 | H | NH | C(Me) 2 | OMe |
1-861 | 1 | H | NH | C(Me) 2 | OEt |
1-862 | 1 | H | NH | C(Me) 2 | OCH 2Ph |
1-863 | 1 | H | NH | C(Me) 2 | NHSO 2Me |
1-864 | 1 | H | NH | C(Me) 2 | NHSO 2N(Me)(CHMe 2) |
1-865 | 1 | F | NH | C(Me) 2 | OH |
1-866 | 1 | F | NH | C(Me) 2 | OMe |
1-867 | 1 | F | NH | C(Me) 2 | OEt |
1-868 | 1 | F | NH | C(Me) 2 | OCH 2Ph |
1-869 | 1 | F | NH | C(Me) 2 | NHSO 2Me |
1-870 | 1 | F | NH | C(Me) 2 | NHSO 2N(Me)(CHMe 2) |
1-871 | 1 | H | O | CH 2CH 2 | OH |
1-872 | 1 | H | O | CH 2CH 2 | OMe |
1-873 | 1 | H | O | CH 2CH 2 | OEt |
1-874 | 1 | H | O | CH 2CH 2 | OCH 2Ph |
1-875 | 1 | H | O | CH 2CH 2 | NHSO 2Me |
1-876 | 1 | H | O | CH 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-877 | 1 | F | O | CH 2CH 2 | OH |
1-878 | 1 | F | O | CH 2CH 2 | OMe |
1-879 | 1 | F | O | CH 2CH 2 | OEt |
1-880 | 1 | F | O | CH 2CH 2 | OCH 2Ph |
1-881 | 1 | F | O | CH 2CH 2 | NHSO 2Me |
1-882 | 1 | F | O | CH 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-883 | 1 | H | NH | CH 2CH 2 | OH |
1-884 | 1 | H | NH | CH 2CH 2 | OMe |
1-885 | 1 | H | NH | CH 2CH 2 | OEt |
1-886 | 1 | H | NH | CH 2CH 2 | OCH 2Ph |
1-887 | 1 | H | NH | CH 2CH 2 | NHSO 2Me |
1-888 | 1 | H | NH | CH 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-889 | 1 | F | NH | CH 2CH 2 | OH |
1-890 | 1 | F | NH | CH 2CH 2 | OMe |
1-891 | 1 | F | NH | CH 2CH 2 | OEt |
1-892 | 1 | F | NH | CH 2CH 2 | OCH 2Ph |
1-893 | 1 | F | NH | CH 2CH 2 | NHSO 2Me |
1-894 | 1 | F | NH | CH 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-895 | 1 | H | O | CHMeCH 2 | OH |
1-896 | 1 | H | O | CHMeCH 2 | OMe |
1-897 | 1 | H | O | CHMeCH 2 | OEt |
1-898 | 1 | H | O | CHMeCH 2 | OCH 2Ph |
1-899 | 1 | H | O | CHMeCH 2 | NHSO 2Me |
1-900 | 1 | H | O | CHMeCH 2 | NHSO 2N(Me)(CHMe 2) |
1-901 | 1 | F | O | CHMeCH 2 | OH |
1-902 | 1 | F | O | CHMeCH 2 | OMe |
1-903 | 1 | F | O | CHMeCH 2 | OEt |
1-904 | 1 | F | O | CHMeCH 2 | OCH 2Ph |
1-905 | 1 | F | O | CHMeCH 2 | NHSO 2Me |
1-906 | 1 | F | O | CHMeCH 2 | NHSO 2N(Me)(CHMe 2) |
1-907 | 1 | H | NH | CHMeCH 2 | OH |
1-908 | 1 | H | NH | CHMeCH 2 | OMe |
1-909 | 1 | H | NH | CHMeCH 2 | OEt |
1-910 | 1 | H | NH | CHMeCH 2 | OCH 2Ph |
1-911 | 1 | H | NH | CHMeCH 2 | NHSO 2Me |
1-912 | 1 | H | NH | CHMeCH 2 | NHSO 2N(Me)(CHMe 2) |
1-913 | 1 | F | NH | CHMeCH 2 | OH |
1-914 | 1 | F | NH | CHMeCH 2 | OMe |
1-915 | 1 | F | NH | CHMeCH 2 | OEt |
1-916 | 1 | F | NH | CHMeCH 2 | OCH 2Ph |
1-917 | 1 | F | NH | CHMeCH 2 | NHSO 2Me |
1-918 | 1 | F | NH | CHMeCH 2 | NHSO 2N(Me)(CHMe 2) |
1-919 | 1 | H | O | CH 2CHMe | OH |
1-920 | 1 | H | O | CH 2CHMe | OMe |
1-921 | 1 | H | O | CH 2CHMe | OEt |
1-922 | 1 | H | O | CH 2CHMe | OCH 2Ph |
1-923 | 1 | H | O | CH 2CHMe | NHSO 2Me |
1-924 | 1 | H | O | CH 2CHMe | NHSO 2N(Me)(CHMe 2) |
1-925 | 1 | F | O | CH 2CHMe | OH |
1-926 | 1 | F | O | CH 2CHMe | OMe |
1-927 | 1 | F | O | CH 2CHMe | OEt |
1-928 | 1 | F | O | CH 2CHMe | OCH 2Ph |
1-929 | 1 | F | O | CH 2CHMe | NHSO 2Me |
1-930 | 1 | F | O | CH 2CHMe | NHSO 2N(Me)(CHMe 2) |
1-931 | 1 | H | NH | CH 2CHMe | OH |
1-932 | 1 | H | NH | CH 2CHMe | OMe |
1-933 | 1 | H | NH | CH 2CHMe | OEt |
1-934 | 1 | H | NH | CH 2CHMe | OCH 2Ph |
1-935 | 1 | H | NH | CH 2CHMe | NHSO 2Me |
1-936 | 1 | H | NH | CH 2CHMe | NHSO 2N(Me)(CHMe 2) |
1-937 | 1 | F | NH | CH 2CHMe | OH |
1-938 | 1 | F | NH | CH 2CHMe | OMe |
1-939 | 1 | F | NH | CH 2CHMe | OEt |
1-940 | 1 | F | NH | CH 2CHMe | OCH 2Ph |
1-941 | 1 | F | NH | CH 2CHMe | NHSO 2Me |
1-942 | 1 | F | NH | CH 2CHMe | NHSO 2N(Me)(CHMe 2) |
1-943 | 1 | H | O | CMe 2CH 2 | OH |
1-944 | 1 | H | O | CMe 2CH 2 | OMe |
1-945 | 1 | H | O | CMe 2CH 2 | OEt |
1-946 | 1 | H | O | CMe 2CH 2 | OCH 2Ph |
1-947 | 1 | H | O | CMe 2CH 2 | NHSO 2Me |
1-948 | 1 | H | O | CMe 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-949 | 1 | F | O | CMe 2CH 2 | OH |
1-950 | 1 | F | O | CMe 2CH 2 | OMe |
1-951 | 1 | F | O | CMe 2CH 2 | OEt |
1-952 | 1 | F | O | CMe 2CH 2 | OCH 2Ph |
1-953 | 1 | F | O | CMe 2CH 2 | NHSO 2Me |
1-954 | 1 | F | O | CMe 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-955 | 1 | H | NH | CMe 2CH 2 | OH |
1-956 | 1 | H | NH | CMe 2CH 2 | OMe |
1-957 | 1 | H | NH | CMe 2CH 2 | OEt |
1-958 | 1 | H | NH | CMe 2CH 2 | OCH 2Ph |
1-959 | 1 | H | NH | CMe 2CH 2 | NHSO 2Me |
1-960 | 1 | H | NH | CMe 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-961 | 1 | F | NH | CMe 2CH 2 | OH |
1-962 | 1 | F | NH | CMe 2CH 2 | OMe |
1-963 | 1 | F | NH | CMe 2CH 2 | OEt |
1-964 | 1 | F | NH | CMe 2CH 2 | OCH 2Ph |
1-965 | 1 | F | NH | CMe 2CH 2 | NHSO 2Me |
1-966 | 1 | F | NH | CMe 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-967 | 1 | H | O | CH 2CMe 2 | OH |
1-968 | 1 | H | O | CH 2CMe 2 | OMe |
1-969 | 1 | H | O | CH 2CMe 2 | OEt |
1-970 | 1 | H | O | CH 2CMe 2 | OCH 2Ph |
1-971 | 1 | H | O | CH 2CMe 2 | NHSO 2Me |
1-972 | 1 | H | O | CH 2CMe 2 | NHSO 2N(Me)(CHMe 2) |
1-973 | 1 | F | O | CH 2CMe 2 | OH |
1-974 | 1 | F | O | CH 2CMe 2 | OMe |
1-975 | 1 | F | O | CH 2CMe 2 | OEt |
1-976 | 1 | F | O | CH 2CMe 2 | OCH 2Ph |
1-977 | 1 | F | O | CH 2CMe 2 | NHSO 2Me |
1-978 | 1 | F | O | CH 2CMe 2 | NHSO 2N(Me)(CHMe 2) |
1-979 | 1 | H | NH | CH 2CMe 2 | OH |
1-980 | 1 | H | NH | CH 2CMe 2 | OMe |
1-981 | 1 | H | NH | CH 2CMe 2 | OEt |
1-982 | 1 | H | NH | CH 2CMe 2 | OCH 2Ph |
1-983 | 1 | H | NH | CH 2CMe 2 | NHSO 2Me |
1-984 | 1 | H | NH | CH 2CMe 2 | NHSO 2N(Me)(CHMe 2) |
1-985 | 1 | F | NH | CH 2CMe 2 | OH |
1-986 | 1 | F | NH | CH 2CMe 2 | OMe |
1-987 | 1 | F | NH | CH 2CMe 2 | OEt |
1-988 | 1 | F | NH | CH 2CMe 2 | OCH 2Ph |
1-989 | 1 | F | NH | CH 2CMe 2 | NHSO 2Me |
1-990 | 1 | F | NH | CH 2CMe 2 | NHSO 2N(Me)(CHMe 2) |
1-991 | 1 | H | O | CH 2CH 2CH 2 | OH |
1-992 | 1 | H | O | CH 2CH 2CH 2 | OMe |
1-993 | 1 | H | O | CH 2CH 2CH 2 | OEt |
1-994 | 1 | H | O | CH 2CH 2CH 2 | OCH 2Ph |
1-995 | 1 | H | O | CH 2CH 2CH 2 | NHSO 2Me |
1-996 | 1 | H | O | CH 2CH 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-997 | 1 | F | O | CH 2CH 2CH 2 | OH |
1-998 | 1 | F | O | CH 2CH 2CH 2 | OMe |
1-999 | 1 | F | O | CH 2CH 2CH 2 | OEt |
1-1000 | 1 | F | O | CH 2CH 2CH 2 | OCH 2Ph |
1-1001 | 1 | F | O | CH 2CH 2CH 2 | NHSO 2Me |
1-1002 | 1 | F | O | CH 2CH 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-1003 | 1 | H | NH | CH 2CH 2CH 2 | OH |
1-1004 | 1 | H | NH | CH 2CH 2CH 2 | OMe |
1-1005 | 1 | H | NH | CH 2CH 2CH 2 | OEt |
1-1006 | 1 | H | NH | CH 2CH 2CH 2 | OCH 2Ph |
1-1007 | 1 | H | NH | CH 2CH 2CH 2 | NHSO 2Me |
1-1008 | 1 | H | NH | CH 2CH 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-1009 | 1 | F | NH | CH 2CH 2CH 2 | OH |
1-1010 | 1 | F | NH | CH 2CH 2CH 2 | OMe |
1-1011 | 1 | F | NH | CH 2CH 2CH 2 | OEt |
1-1012 | 1 | F | NH | CH 2CH 2CH 2 | OCH 2Ph |
1-1013 | 1 | F | NH | CH 2CH 2CH 2 | NHSO 2Me |
1-1014 | 1 | F | NH | CH 2CH 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-1015 | 2 | H | O | CH 2 | OH |
1-1016 | 2 | H | O | CH 2 | OMe |
1-1017 | 2 | H | O | CH 2 | OEt |
1-1018 | 2 | H | O | CH 2 | OCH 2Ph |
1-1019 | 2 | H | O | CH 2 | NHSO 2Me |
1-1020 | 2 | H | O | CH 2 | NHSO 2N(Me)(CHMe 2) |
1-1021 | 2 | F | O | CH 2 | OH |
1-1022 | 2 | F | O | CH 2 | OMe |
1-1023 | 2 | F | O | CH 2 | OEt |
1-1024 | 2 | F | O | CH 2 | OCH 2Ph |
1-1025 | 2 | F | O | CH 2 | NHSO 2Me |
1-1026 | 2 | F | O | CH 2 | NHSO 2N(Me)(CHMe 2) |
1-1027 | 2 | H | NH | CH 2 | OH |
1-1028 | 2 | H | NH | CH 2 | OMe |
1-1029 | 2 | H | NH | CH 2 | OEt |
1-1030 | 2 | H | NH | CH 2 | OCH 2Ph |
1-1031 | 2 | H | NH | CH 2 | NHSO 2Me |
1-1032 | 2 | H | NH | CH 2 | NHSO 2N(Me)(CHMe 2) |
1-1033 | 2 | F | NH | CH 2 | OH |
1-1034 | 2 | F | NH | CH 2 | OMe |
1-1035 | 2 | F | NH | CH 2 | OEt |
1-1036 | 2 | F | NH | CH 2 | OCH 2Ph |
1-1037 | 2 | F | NH | CH 2 | NHSO 2Me |
1-1038 | 2 | F | NH | CH 2 | NHSO 2N(Me)(CHMe 2) |
1-1039 | 2 | H | O | CHMe | OH |
1-1040 | 2 | H | O | CHMe | OMe |
1-1041 | 2 | H | O | CHMe | OEt |
1-1042 | 2 | H | O | CHMe | OCH 2Ph |
1-1043 | 2 | H | O | CHMe | NHSO 2Me |
1-1044 | 2 | H | O | CHMe | NHSO 2N(Me)(CHMe 2) |
1-1045 | 2 | F | O | CHMe | OH |
1-1046 | 2 | F | O | CHMe | OMe |
1-1047 | 2 | F | O | CHMe | OEt |
1-1048 | 2 | F | O | CHMe | OCH 2Ph |
1-1049 | 2 | F | O | CHMe | NHSO 2Me |
1-1050 | 2 | F | O | CHMe | NHSO 2N(Me)(CHMe 2) |
1-1051 | 2 | H | NH | CHMe | OH |
1-1052 | 2 | H | NH | CHMe | OMe |
1-1053 | 2 | H | NH | CHMe | OEt |
1-1054 | 2 | H | NH | CHMe | OCH 2Ph |
1-1055 | 2 | H | NH | CHMe | NHSO 2Me |
1-1056 | 2 | H | NH | CHMe | NHSO 2N(Me)(CHMe 2) |
1-1057 | 2 | F | NH | CHMe | OH |
1-1058 | 2 | F | NH | CHMe | OMe |
1-1059 | 2 | F | NH | CHMe | OEt |
1-1060 | 2 | F | NH | CHMe | OCH 2Ph |
1-1061 | 2 | F | NH | CHMe | NHSO 2Me |
1-1062 | 2 | F | NH | CHMe | NHSO 2N(Me)(CHMe 2) |
1-1063 | 2 | H | O | C(Me) 2 | OH |
1-1064 | 2 | H | O | C(Me) 2 | OMe |
1-1065 | 2 | H | O | C(Me) 2 | OEt |
1-1066 | 2 | H | O | C(Me) 2 | OCH 2Ph |
1-1067 | 2 | H | O | C(Me) 2 | NHSO 2Me |
1-1068 | 2 | H | O | C(Me) 2 | NHSO 2N(Me)(CHMe 2) |
1-1069 | 2 | F | O | C(Me) 2 | OH |
1-1070 | 2 | F | O | C(Me) 2 | OMe |
1-1071 | 2 | F | O | C(Me) 2 | OEt |
1-1072 | 2 | F | O | C(Me) 2 | OCH 2Ph |
1-1073 | 2 | F | O | C(Me) 2 | NHSO 2Me |
1-1074 | 2 | F | O | C(Me) 2 | NHSO 2N(Me)(CHMe 2) |
1-1075 | 2 | H | NH | C(Me) 2 | OH |
1-1076 | 2 | H | NH | C(Me) 2 | OMe |
1-1077 | 2 | H | NH | C(Me) 2 | OEt |
1-1078 | 2 | H | NH | C(Me) 2 | OCH 2Ph |
1-1079 | 2 | H | NH | C(Me) 2 | NHSO 2Me |
1-1080 | 2 | H | NH | C(Me) 2 | NHSO 2N(Me)(CHMe 2) |
1-1081 | 2 | F | NH | C(Me) 2 | OH |
1-1082 | 2 | F | NH | C(Me) 2 | OMe |
1-1083 | 2 | F | NH | C(Me) 2 | OEt |
1-1084 | 2 | F | NH | C(Me) 2 | OCH 2Ph |
1-1085 | 2 | F | NH | C(Me) 2 | NHSO 2Me |
1-1086 | 2 | F | NH | C(Me) 2 | NHSO 2N(Me)(CHMe 2) |
1-1087 | 2 | H | O | CH 2CH 2 | OH |
1-1088 | 2 | H | O | CH 2CH 2 | OMe |
1-1089 | 2 | H | O | CH 2CH 2 | OEt |
1-1090 | 2 | H | O | CH 2CH 2 | OCH 2Ph |
1-1091 | 2 | H | O | CH 2CH 2 | NHSO 2Me |
1-1092 | 2 | H | O | CH 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-1093 | 2 | F | O | CH 2CH 2 | OH |
1-1094 | 2 | F | O | CH 2CH 2 | OMe |
1-1095 | 2 | F | O | CH 2CH 2 | OEt |
1-1096 | 2 | F | O | CH 2CH 2 | OCH 2Ph |
1-1097 | 2 | F | O | CH 2CH 2 | NHSO 2Me |
1-1098 | 2 | F | O | CH 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-1099 | 2 | H | NH | CH 2CH 2 | OH |
1-1100 | 2 | H | NH | CH 2CH 2 | OMe |
1-1101 | 2 | H | NH | CH 2CH 2 | OEt |
1-1102 | 2 | H | NH | CH 2CH 2 | OCH 2Ph |
1-1103 | 2 | H | NH | CH 2CH 2 | NHSO 2Me |
1-1104 | 2 | H | NH | CH 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-1105 | 2 | F | NH | CH 2CH 2 | OH |
1-1106 | 2 | F | NH | CH 2CH 2 | OMe |
1-1107 | 2 | F | NH | CH 2CH 2 | OEt |
1-1108 | 2 | F | NH | CH 2CH 2 | OCH 2Ph |
1-1109 | 2 | F | NH | CH 2CH 2 | NHSO 2Me |
1-1110 | 2 | F | NH | CH 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-1111 | 2 | H | O | CHMeCH 2 | OH |
1-1112 | 2 | H | O | CHMeCH 2 | OMe |
1-1113 | 2 | H | O | CHMeCH 2 | OEt |
1-1114 | 2 | H | O | CHMeCH 2 | OCH 2Ph |
1-1115 | 2 | H | O | CHMeCH 2 | NHSO 2Me |
1-1116 | 2 | H | O | CHMeCH 2 | NHSO 2N(Me)(CHMe 2) |
1-1117 | 2 | F | O | CHMeCH 2 | OH |
1-1118 | 2 | F | O | CHMeCH 2 | OMe |
1-1119 | 2 | F | O | CHMeCH 2 | OEt |
1-1120 | 2 | F | O | CHMeCH 2 | OCH 2Ph |
1-1121 | 2 | F | O | CHMeCH 2 | NHSO 2Me |
1-1122 | 2 | F | O | CHMeCH 2 | NHSO 2N(Me)(CHMe 2) |
1-1123 | 2 | H | NH | CHMeCH 2 | OH |
1-1124 | 2 | H | NH | CHMeCH 2 | OMe |
1-1125 | 2 | H | NH | CHMeCH 2 | OEt |
1-1126 | 2 | H | NH | CHMeCH 2 | OCH 2Ph |
1-1127 | 2 | H | NH | CHMeCH 2 | NHSO 2Me |
1-1128 | 2 | H | NH | CHMeCH 2 | NHSO 2N(Me)(CHMe 2) |
1-1129 | 2 | F | NH | CHMeCH 2 | OH |
1-1130 | 2 | F | NH | CHMeCH 2 | OMe |
1-1131 | 2 | F | NH | CHMeCH 2 | OEt |
1-1132 | 2 | F | NH | CHMeCH 2 | OCH 2Ph |
1-1133 | 2 | F | NH | CHMeCH 2 | NHSO 2Me |
1-1134 | 2 | F | NH | CHMeCH 2 | NHSO 2N(Me)(CHMe 2) |
1-1135 | 2 | H | O | CH 2CHMe | OH |
1-1136 | 2 | H | O | CH 2CHMe | OMe |
1-1137 | 2 | H | O | CH 2CHMe | OEt |
1-1138 | 2 | H | O | CH 2CHMe | OCH 2Ph |
1-1139 | 2 | H | O | CH 2CHMe | NHSO 2Me |
1-1140 | 2 | H | O | CH 2CHMe | NHSO 2N(Me)(CHMe 2) |
1-1141 | 2 | F | O | CH 2CHMe | OH |
1-1142 | 2 | F | O | CH 2CHMe | OMe |
1-1143 | 2 | F | O | CH 2CHMe | OEt |
1-1144 | 2 | F | O | CH 2CHMe | OCH 2Ph |
1-1145 | 2 | F | O | CH 2CHMe | NHSO 2Me |
1-1146 | 2 | F | O | CH 2CHMe | NHSO 2N(Me)(CHMe 2) |
1-1147 | 2 | H | NH | CH 2CHMe | OH |
1-1148 | 2 | H | NH | CH 2CHMe | OMe |
1-1149 | 2 | H | NH | CH 2CHMe | OEt |
1-1150 | 2 | H | NH | CH 2CHMe | OCH 2Ph |
1-1151 | 2 | H | NH | CH 2CHMe | NHSO 2Me |
1-1152 | 2 | H | NH | CH 2CHMe | NHSO 2N(Me)(CHMe 2) |
1-1153 | 2 | F | NH | CH 2CHMe | OH |
1-1154 | 2 | F | NH | CH 2CHMe | OMe |
1-1155 | 2 | F | NH | CH 2CHMe | OEt |
1-1156 | 2 | F | NH | CH 2CHMe | OCH 2Ph |
1-1157 | 2 | F | NH | CH 2CHMe | NHSO 2Me |
1-1158 | 2 | F | NH | CH 2CHMe | NHSO 2N(Me)(CHMe 2) |
1-1159 | 2 | H | O | CMe 2CH 2 | OH |
1-1160 | 2 | H | O | CMe 2CH 2 | OMe |
1-1161 | 2 | H | O | CMe 2CH 2 | OEt |
1-1162 | 2 | H | O | CMe 2CH 2 | OCH 2Ph |
1-1163 | 2 | H | O | CMe 2CH 2 | NHSO 2Me |
1-1164 | 2 | H | O | CMe 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-1165 | 2 | F | O | CMe 2CH 2 | OH |
1-1166 | 2 | F | O | CMe 2CH 2 | OMe |
1-1167 | 2 | F | O | CMe 2CH 2 | OEt |
1-1168 | 2 | F | O | CMe 2CH 2 | OCH 2Ph |
1-1169 | 2 | F | O | CMe 2CH 2 | NHSO 2Me |
1-1170 | 2 | F | O | CMe 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-1171 | 2 | H | NH | CMe 2CH 2 | OH |
1-1172 | 2 | H | NH | CMe 2CH 2 | OMe |
1-1173 | 2 | H | NH | CMe 2CH 2 | OEt |
1-1174 | 2 | H | NH | CMe 2CH 2 | OCH 2Ph |
1-1175 | 2 | H | NH | CMe 2CH 2 | NHSO 2Me |
1-1176 | 2 | H | NH | CMe 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-1177 | 2 | F | NH | CMe 2CH 2 | OH |
1-1178 | 2 | F | NH | CMe 2CH 2 | OMe |
1-1179 | 2 | F | NH | CMe 2CH 2 | OEt |
1-1180 | 2 | F | NH | CMe 2CH 2 | OCH 2Ph |
1-1181 | 2 | F | NH | CMe 2CH 2 | NHSO 2Me |
1-1182 | 2 | F | NH | CMe 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-1183 | 2 | H | O | CH 2CMe 2 | OH |
1-1184 | 2 | H | O | CH 2CMe 2 | OMe |
1-1185 | 2 | H | O | CH 2CMe 2 | OEt |
1-1186 | 2 | H | O | CH 2CMe 2 | OCH 2Ph |
1-1187 | 2 | H | O | CH 2CMe 2 | NHSO 2Me |
1-1188 | 2 | H | O | CH 2CMe 2 | NHSO 2N(Me)(CHMe 2) |
1-1189 | 2 | F | O | CH 2CMe 2 | OH |
1-1190 | 2 | F | O | CH 2CMe 2 | OMe |
1-1191 | 2 | F | O | CH 2CMe 2 | OEt |
1-1192 | 2 | F | O | CH 2CMe 2 | OCH 2Ph |
1-1193 | 2 | F | O | CH 2CMe 2 | NHSO 2Me |
1-1194 | 2 | F | O | CH 2CMe 2 | NHSO 2N(Me)(CHMe 2) |
1-1195 | 2 | H | NH | CH 2CMe 2 | OH |
1-1196 | 2 | H | NH | CH 2CMe 2 | OMe |
1-1197 | 2 | H | NH | CH 2CMe 2 | OEt |
1-1198 | 2 | H | NH | CH 2CMe 2 | OCH 2Ph |
1-1199 | 2 | H | NH | CH 2CMe 2 | NHSO 2Me |
1-1200 | 2 | H | NH | CH 2CMe 2 | NHSO 2N(Me)(CHMe 2) |
1-1201 | 2 | F | NH | CH 2CMe 2 | OH |
1-1202 | 2 | F | NH | CH 2CMe 2 | OMe |
1-1203 | 2 | F | NH | CH 2CMe 2 | OEt |
1-1204 | 2 | F | NH | CH 2CMe 2 | OCH 2Ph |
1-1205 | 2 | F | NH | CH 2CMe 2 | NHSO 2Me |
1-1206 | 2 | F | NH | CH 2CMe 2 | NHSO 2N(Me)(CHMe 2) |
1-1207 | 2 | H | O | CH 2CH 2CH 2 | OH |
1-1208 | 2 | H | O | CH 2CH 2CH 2 | OMe |
1-1209 | 2 | H | O | CH 2CH 2CH 2 | OEt |
1-1210 | 2 | H | O | CH 2CH 2CH 2 | OCH 2Ph |
1-1211 | 2 | H | O | CH 2CH 2CH 2 | NHSO 2Me |
1-1212 | 2 | H | O | CH 2CH 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-1213 | 2 | F | O | CH 2CH 2CH 2 | OH |
1-1214 | 2 | F | O | CH 2CH 2CH 2 | OMe |
1-1215 | 2 | F | O | CH 2CH 2CH 2 | OEt |
1-1216 | 2 | F | O | CH 2CH 2CH 2 | OCH 2Ph |
1-1217 | 2 | F | O | CH 2CH 2CH 2 | NHSO 2Me |
1-1218 | 2 | F | O | CH 2CH 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-1219 | 2 | H | NH | CH 2CH 2CH 2 | OH |
1-1220 | 2 | H | NH | CH 2CH 2CH 2 | OMe |
1-1221 | 2 | H | NH | CH 2CH 2CH 2 | OEt |
1-1222 | 2 | H | NH | CH 2CH 2CH 2 | OCH 2Ph |
1-1223 | 2 | H | NH | CH 2CH 2CH 2 | NHSO 2Me |
1-1224 | 2 | H | NH | CH 2CH 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1-1225 | 2 | F | NH | CH 2CH 2CH 2 | OH |
1-1226 | 2 | F | NH | CH 2CH 2CH 2 | OMe |
1-1227 | 2 | F | NH | CH 2CH 2CH 2 | OEt |
1-1228 | 2 | F | NH | CH 2CH 2CH 2 | OCH 2Ph |
1-1229 | 2 | F | NH | CH 2CH 2CH 2 | NHSO 2Me |
1-1230 | 2 | F | NH | CH 2CH 2CH 2 | NHSO 2N(Me)(CHMe 2) |
1230種具有式 (I) 的化合物,其中X
1和X
2係硫,X
3係氧,R
1和R
2係甲基,R
4係氯,R
16和R
17係氫,並且Y係C-H,並且m、B、D、R
3和R
8的值係如表1中對於化合物1-1至1-1230給出的,被分別標示為化合物編號2-1至2-1230。
1230種具有式 (I) 的化合物,其中X
1係硫,X
2和X
3係氧,R
1和R
2係甲基,R
4係氯,R
16和R
17係氫,並且Y係N,並且m、B、D、R
3和R
8的值係如表1中對於化合物1-1至1-1230給出的,被分別標示為化合物編號3-1至3-1230。
1230種具有式 (I) 的化合物,其中X
1和X
2係硫,X
3係氧,R
1和R
2係甲基,R
4係氯,R
16和R
17係氫,並且Y係N,並且m、B、D、R
3和R
8的值係如表1中對於化合物1-1至1-1230給出的,被分別標示為化合物編號4-1至4-1230。
1230種具有式 (I) 的化合物,其中X
1係硫,X
2和X
3係氧,R
1和R
2係甲基,R
4係CN,R
16和R
17係氫,並且Y係N,並且m、B、D、R
3和R
8的值係如表1中對於化合物1-1至1-1230給出的,被分別標示為化合物編號5-1至5-1230。
1230種具有式 (I) 的化合物,其中X
1和X
2係硫,X
3係氧,R
1和R
2係甲基,R
4係CN,R
16和R
17係氫,並且Y係C-H,並且m、B、D、R
3和R
8的值係如表1中對於化合物1-1至1-1230給出的,被分別標示為化合物編號6-1至6-1230。
1230種具有式 (I) 的化合物,其中X
1係硫,X
2和X
3係氧,R
1和R
2係甲基,R
4係溴,R
16和R
17係氫,並且Y係N,並且m、B、D、R
3和R
8的值係如表1中對於化合物1-1至1-1230給出的,被分別標示為化合物編號7-1至7-1230。
1230種具有式 (I) 的化合物,其中X
1和X
2係硫,X
3係氧,R
1和R
2係甲基,R
4係溴,R
16和R
17係氫,並且Y係C-H,並且m、B、D、R
3和R
8的值係如表1中對於化合物1-1至1-1230給出的,被分別標示為化合物編號8-1至8-1230。
1230種具有式 (I) 的化合物,其中X
1係硫,X
2和X
3係氧,R
1和R
2係甲基,R
4係氯,R
16係氫,R
17係甲基,並且Y係C-H,並且m、B、D、R
3和R
8的值係如表1中對於化合物1-1至1-1230給出的,被分別標示為化合物編號9-1至9-1230。
1230種具有式 (I) 的化合物,其中X
1和X
2係硫,X
3係氧,R
1和R
2係甲基,R
4係氯,R
16係氫,R
17係甲基,並且Y係C-H,並且m、B、D、R
3和R
8的值係如表1中對於化合物1-1至1-1230給出的,被分別標示為化合物編號10-1至10-1230。
1230種具有式 (I) 的化合物,其中X
1係硫,X
2和X
3係氧,R
1和R
2係甲基,R
4係氯,R
16係氫,R
17係甲基,並且Y係N,並且m、B、D、R
3和R
8的值係如表1中對於化合物1-1至1-1230給出的,被分別標示為化合物編號11-1至11-1230。
1230種具有式 (I) 的化合物,其中X
1和X
2係硫,X
3係氧,R
1和R
2係甲基,R
4係氯,R
16係氫,R
17係甲基,並且Y係N,並且m、B、D、R
3和R
8的值係如表1中對於化合物1-1至1-1230給出的,被分別標示為化合物編號12-1至12-1230。
1230種具有式 (I) 的化合物,其中X
1係硫,X
2和X
3係氧,R
1和R
2係甲基,R
4係CN,R
16係氫,R
17係甲基,並且Y係N,並且m、B、D、R
3和R
8的值係如表1中對於化合物1-1至1-1230給出的,被分別標示為化合物編號13-1至13-1230。
1230種具有式 (I) 的化合物,其中X
1和X
2係硫,X
3係氧,R
1和R
2係甲基,R
4係CN,R
16係氫,R
17係甲基,並且Y係C-H,並且m、B、D、R
3和R
8的值係如表1中對於化合物1-1至1-1230給出的,被分別標示為化合物編號14-1至14-1230。
1230種具有式 (I) 的化合物,其中X
1係硫,X
2和X
3係氧,R
1和R
2係甲基,R
4係溴,R
16係氫,R
17係甲基,並且Y係N,並且m、B、D、R
3和R
8的值係如表1中對於化合物1-1至1-1230給出的,被分別標示為化合物編號15-1至15-1230。
1230種具有式 (I) 的化合物,其中X
1和X
2係硫,X
3係氧,R
1和R
2係甲基,R
4係溴,R
16係氫,R
17係甲基,並且Y係C-H,並且m、B、D、R
3和R
8的值係如表1中對於化合物1-1至1-1230給出的,被分別標示為化合物編號16-1至16-1230。
1230種具有式 (I) 的化合物,其中X
1係硫,X
2和X
3係氧,R
1和R
2係甲基,R
4係氯,R
16和R
17係甲基,並且Y係C-H,並且m、B、D、R
3和R
8的值係如表1中對於化合物1-1至1-1230給出的,被分別標示為化合物編號17-1至17-1230。
1230種具有式 (I) 的化合物,其中X
1和X
2係硫,X
3係氧,R
1和R
2係甲基,R
4係氯,R
16和R
17係甲基,並且Y係C-H,並且m、B、D、R
3和R
8的值係如表1中對於化合物1-1至1-1230給出的,被分別標示為化合物編號18-1至18-1230。
1230種具有式 (I) 的化合物,其中X
1係硫,X
2和X
3係氧,R
1和R
2係甲基,R
4係氯,R
16和R
17係甲基,並且Y係N,並且m、B、D、R
3和R
8的值係如表1中對於化合物1-1至1-1230給出的,被分別標示為化合物編號19-1至19-1230。
1230種具有式 (I) 的化合物,其中X
1和X
2係硫,X
3係氧,R
1和R
2係甲基,R
4係氯,R
16和R
17係甲基,並且Y係N,並且m、B、D、R
3和R
8的值係如表1中對於化合物1-1至1-1230給出的,被分別標示為化合物編號20-1至20-1230。
1230種具有式 (I) 的化合物,其中X
1係硫,X
2和X
3係氧,R
1和R
2係甲基,R
4係CN,R
16和R
17係甲基,並且Y係N,並且m、B、D、R
3和R
8的值係如表1中對於化合物1-1至1-1230給出的,被分別標示為化合物編號21-1至21-1230。
1230種具有式 (I) 的化合物,其中X
1和X
2係硫,X
3係氧,R
1和R
2係甲基,R
4係CN,R
16和R
17係甲基,並且Y係C-H,並且m、B、D、R
3和R
8的值係如表1中對於化合物1-1至1-1230給出的,被分別標示為化合物編號22-1至22-1230。
1230種具有式 (I) 的化合物,其中X
1係硫,X
2和X
3係氧,R
1和R
2係甲基,R
4係溴,R
16和R
17係甲基,並且Y係N,並且m、B、D、R
3和R
8的值係如表1中對於化合物1-1至1-1230給出的,被分別標示為化合物編號23-1至23-1230。
1230種具有式 (I) 的化合物,其中X
1和X
2係硫,X
3係氧,R
1和R
2係甲基,R
4係溴,R
16和R
17係甲基,並且Y係C-H,並且m、B、D、R
3和R
8的值係如表1中對於化合物1-1至1-1230給出的,被分別標示為化合物編號24-1至24-1230。
本發明之化合物可以藉由有機化學領域的技術人員已知的技術製備。下文描述了用於生產具有式 (I) 的化合物的通用方法。除非在本文中另外說明,否則取代基m、X
1、X
2、X
3、Y、B、D、R
1、R
2、R
3、R
4、R
5、R
6、R
7、R
8、R
9、R
10、R
11、R
12、R
13、R
14、R
15、R
16和R
17係如上文所定義的。用於製備本發明之化合物的起始材料可以購買自通常的商品供應商或者可以藉由已知之方法製備。起始材料以及中間體可以在用於下一步驟之前,藉由先前技術之方法(如層析、結晶、蒸餾和過濾)進行純化。
可以由具有式 (A) 的化合物和具有式 (B) 的化合物製備具有式 (I) 的化合物,如在反應流程1中所示。
反應流程 1
例如,具有式 (A) 的化合物和具有式 (B) 的化合物的混合物可以在合適的溶劑(如甲苯)中用鹼(如三乙胺)和羰基轉移試劑(如光氣或羰基二咪唑)進行處理。具有式 (A) 的脲或硫脲係可獲得的或可以藉由文獻中眾所周知之方法製備。可以由具有式 (C) 的苯胺製備具有式 (B) 的化合物,如在反應流程2中所示。
反應流程 2
例如,具有式 (C) 的化合物可以在合適的溶劑(如甲苯)中用羰基或硫代羰基轉移試劑(如雙光氣、三光氣或硫光氣)進行處理。可以由具有式 (D) 的硝基化合物製備具有式 (C) 的苯胺,如在反應流程3中所示。
反應流程 3
例如,具有式 (D) 的化合物可以在合適的溶劑(如水和乙醇的混合物)中用還原劑(如鐵和氯化銨)進行處理。可以由具有式 (E) 的硫醇和具有式 (F) 的化合物(其中LG表示脫離基,例如鹵素原子,如氯原子)製備具有式 (D) 的硝基化合物(其中m = 0),如在反應流程4中所示。
反應流程 4
例如,具有式 (E) 的硝基化合物可以在鹼(如三乙胺)的存在下在合適的溶劑(如乙腈)中用具有式 (F) 的化合物進行處理。具有式 (E) 的硝基化合物係可獲得的或可以藉由文獻中眾所周知之方法製備。可以由具有式 (G) 的醇或胺和具有式 (H) 的酸製備具有式 (F) 的化合物,如在反應流程5中所示。
反應流程 5
例如,具有式 (H) 的酸可以在合適的溶劑(如二氯甲烷和二甲基甲醯胺)中用活化劑(如草醯氯)進行處理,並且所得中間體然後在鹼(如三乙胺)的存在下在合適的溶劑(如二氯甲烷)中用具有式 (G) 的醇或胺進行處理。具有式 (G) 的醇和胺以及具有式 (H) 的酸係可獲得的或可以藉由文獻中眾所周知之方法製備。可替代地,可以由具有式 (F) 的化合物和具有式 (J) 的硫醇製備具有式 (I-A) 的化合物(其係具有式 (I) 的化合物,其中m = 0),如在反應流程6中所示。
反應流程 6
例如,具有式 (J) 的硫醇可以在鹼(如三乙胺)的存在下在合適的溶劑(如乙腈)中用具有式 (F) 化合物進行處理。可以由具有式 (K) 的磺醯氯製備具有式 (J) 的硫醇,如在反應流程7中所示。
反應流程 7
例如,具有式 (K) 的磺醯氯可以在合適的溶劑(如水和乙酸的混合物)中用還原劑(如二氯化錫)進行處理。可以由具有式 (L) 的化合物製備具有式 (K) 的磺醯氯,如在反應流程8中所示。
反應流程 8
例如,具有式 (L) 的化合物可以用磺醯化劑(如氯磺酸)進行處理。可以由具有式 (A) 的化合物和具有式 (M) 的化合物製備具有式 (L) 的化合物,如在反應流程9中所示。
反應流程 9
例如,具有式 (A) 的化合物和具有式 (M) 的化合物的混合物可以在合適的溶劑(如甲苯)中用鹼(如三乙胺)和羰基轉移試劑(如光氣或羰基二咪唑)進行處理。可以由具有式 (N) 的苯胺製備具有式 (M) 的化合物,如在反應流程10中所示。
反應流程 10
例如,具有式 (N) 的化合物可以在合適的溶劑(如甲苯)中由羰基或硫代羰基轉移試劑(如雙光氣、三光氣或硫光氣)進行處理。具有式 (N) 的苯胺係可獲得的或可以藉由文獻中眾所周知之方法製備。還可以由具有式 (P) 的酸和具有式 (G) 的醇或胺製備具有式 (I) 的化合物,如在反應流程11中所示。
反應流程 11
例如,具有式 (P) 的酸可以在合適的溶劑(如二氯甲烷和二甲基甲醯胺)中用活化劑(如草醯氯)進行處理,並且所得中間體然後在鹼(如三乙胺)的存在下在合適的溶劑(如二氯甲烷)中用具有式 (G) 的醇或胺進行處理。可以由具有式 (Q) 的酯(其中R表示烷基或類似基團)製備具有式 (P) 的酸,如在反應流程12中所示。
反應流程 12
例如,具有式 (Q) 的化合物可以在合適的溶劑(如二㗁𠮿(dioxane))中用鹽酸進行處理。可以由具有式 (J) 的硫醇和具有式 (R) 的酯(其中LG表示脫離基,例如鹵素原子,如氯原子,並且R表示烷基或類似基團)製備具有式 (Q) 的酯(其中m = 0),如在反應流程13中所示。
反應流程 13
例如,具有式 (J) 的硫醇可以在合適的溶劑(如乙腈)中在鹼(如三乙胺)的存在下用具有式 (R) 的化合物進行處理。具有式 (R) 的酯係可獲得的或可以藉由文獻中眾所周知之方法製備。可以由具有式 (I-A) 的化合物(其係具有式 (I) 的化合物,其中m = 0)製備具有式 (I-B)的化合物(其係具有式 (I) 的化合物,其中m = 1或2),如在反應流程14中所示。
反應流程 14
例如,具有式 (I-A) 的化合物可以在合適的溶劑(如乙腈或二氯甲烷)中用氧化劑(例如過氧單磺酸鉀(oxone)或間氯過氧苯甲酸)進行處理。可以由具有式 (I-D) 的化合物(其係具有式 (I) 的化合物,其中R
8係OR
9)製備具有式 (I-C) 的化合物(其係具有式 (I) 的化合物,其中R
8係OH基團),如在反應流程15中所示。
反應流程 15
例如,具有式 (I-D) 的化合物可以在合適的溶劑(如二㗁𠮿)中用鹽酸進行處理。可以由具有式 (I-C) 的化合物製備具有式 (I-E)的化合物(其係具有式 (I) 的化合物,其中R
8係NR
10R
11),如在反應流程16中所示。
反應流程 16
例如,具有式 (I-C) 的化合物可以在合適的溶劑(如二氯甲烷)中用鹵化試劑(如草醯氯)進行處理以形成醯鹵,該醯鹵可以在鹼(如三乙胺)的存在下在合適的溶劑(如二氯甲烷)中用試劑HNR
10R
11進行處理。
熟悉該項技術者將認識到,經常可以改變進行以上所述之轉化的順序或以可替代的方式將它們組合以製備各種具有式 (I) 的化合物。單個反應中也可以組合多個步驟。預期所有此類變化在本發明之範圍之內。
技術人員還將意識到一些試劑將與如本文定義的取代基m、X
1、X
2、X
3、Y、B、D、R
1、R
2、R
3、R
4、R
5、R
6、R
7、R
8、R
9、R
10、R
11、R
12、R
13、R
14、R
15、R
16和R
17的某些值或組合不相容,並且任何附加的步驟,如保護和/或去保護步驟(實現所希望的轉化需要的)對於技術人員將是清楚的。
根據本發明之化合物可以按未經修飾的形式用作除草劑,但它們通常以多種方式使用配製佐劑(如載劑、溶劑和表面活性物質)被配製成組成物。該等配製物可以處於不同的實體形式,例如,處於以下形式:撒粉劑、凝膠、可濕性粉劑、水可分散性顆粒劑、水可分散性片劑、發泡顆粒、可乳化的濃縮物、微可乳化濃縮物、水包油乳劑、可流動油、水性分散體、油性分散體、懸乳劑、膠囊懸浮液、可乳化的顆粒劑、可溶性液體、水可溶性濃縮物(以水或水混溶性有機溶劑作為載劑)、浸漬的聚合物膜或處於已知的其他形式,例如從Manual on Development and Use of FAO and WHO Specifications for Pesticides[關於殺有害生物劑的FAO和WHO標準的發展和使用的手冊],聯合國,第1版,二次修訂(2010)中已知的。對於水溶性化合物,較佳的是可溶性液體、水溶性濃縮物或水溶性顆粒劑。此類配製物可以直接使用或者可以使用前稀釋再使用。可以用例如水、液體肥料、微量營養素、生物有機體、油或溶劑來進行稀釋。
可以藉由例如將活性成分與配製佐劑混合來製備該等配製物以便獲得處於精細分散固體、顆粒、溶液、分散體或乳液形式的組成物。該等活性成分還可以與其他佐劑(例如精細分散固體、礦物油、植物或動物來源的油、經修飾的植物或動物來源的油、有機溶劑、水、表面活性物質或其組合)來一起配製。
該等活性成分還可以被包含於非常精細的微膠囊中。微膠囊在多孔載劑中含有活性成分。這使得活性成分能夠以受控的量釋放(例如,緩慢釋放)到環境中。微膠囊通常具有從0.1至500微米的直徑。它們包含的活性成分的量按重量計係膠囊重量的約從25%至95%。該等活性成分可以處於整體性的固體的形式、處於固體或液體分散體中的精細顆粒的形式或處於適合溶液的形式。包囊的膜可以包含例如天然的或合成的橡膠、纖維素、苯乙烯/丁二烯共聚物、聚丙烯腈、聚丙烯酸酯、聚酯、聚醯胺、聚脲、聚胺酯或經化學修飾的聚合物以及澱粉黃原酸酯、或熟悉該項技術者已知的其他聚合物。可替代地,可以形成非常精細的微膠囊,其中活性成分在基礎物質的固體基質中是以精細分散顆粒的形式被包含的,但該等微膠囊本身未經包裹。
適合於製備根據本發明之組成物的配製佐劑本身係已知的。作為液體載劑可以使用:水、甲苯、二甲苯、石油醚、植物油、丙酮、甲基乙基酮、環己酮、酸酐、乙腈、乙醯苯、乙酸戊酯、2-丁酮、碳酸丁烯酯、氯苯、環己烷、環己醇、乙酸烷基酯、二丙酮醇、1,2-二氯丙烷、二乙醇胺、對-二乙基苯、二甘醇、松脂酸二乙二醇酯、二甘醇丁基醚、二甘醇乙基醚、二甘醇甲醚、
N,N-二甲基甲醯胺、二甲基亞碸、1,4-二㗁𠮿、二丙二醇、二丙二醇甲基醚、雙丙甘醇二苯甲酸酯、二丙二醇、烷基吡咯啶酮、乙酸乙酯、2-乙基己醇、碳酸乙烯酯、1,1,1-三氯乙烷、2-庚酮、α-蒎烯、d-薴烯、乳酸乙酯、乙二醇、乙二醇丁基醚、乙二醇甲基醚、γ-丁內酯、丙三醇、乙酸甘油酯、二乙酸甘油酯、三乙酸甘油酯、十六烷、己二醇、乙酸異戊基酯、乙酸異冰片基(bornyl)酯、異辛烷、異佛耳酮、異丙苯、肉豆蔻酸異丙酯、乳酸、月桂胺、亞異丙基丙酮、甲氧基丙醇、甲基異戊基酮、甲基異丁基酮、月桂酸甲酯、辛酸甲酯、油酸甲酯、二氯甲烷、間二甲苯、正己烷、正辛胺、十八烷酸、辛胺乙酸酯、油酸、油胺、鄰二甲苯、苯酚、聚乙二醇、丙酸、乳酸丙酯、碳酸丙烯酯、丙二醇、丙二醇甲基醚、對-二甲苯、甲苯、磷酸三乙酯、三乙二醇、二甲苯磺酸、石蠟、礦物油、三氯乙烯、全氯乙烯、乙酸乙酯、乙酸戊酯、乙酸丁酯、丙二醇甲基醚、二乙二醇甲基醚、甲醇、乙醇、異丙醇以及更高分子量的醇,例如戊醇、四氫呋喃醇、己醇、辛醇、乙二醇、丙二醇、甘油、
N-甲基-2-吡咯啶酮等。
合適的固體載劑係例如滑石、二氧化鈦、葉蠟石黏土、矽石、厄帖浦石黏土、矽藻土、石灰石、碳酸鈣、膨潤土、鈣蒙脫土、棉籽殼、小麥粉、大豆粉、浮石、木粉、經研磨的胡桃殼、木質素和類似的物質。
許多表面活性物質可以有利地用在固體和液體配製物兩者中,尤其是在使用前可被載劑稀釋的那些配製物中。表面活性物質可以是陰離子的、陽離子的、非離子的或聚合的並且它們可以用作乳化劑、濕潤劑或懸浮劑或用於其他目的。典型的表面活性物質包括例如烷基硫酸酯的鹽,如十二烷基硫酸二乙醇銨;烷基芳基磺酸酯的鹽,如十二烷基苯磺酸鈣;烷基酚/氧化烯加成產物,如乙氧基化壬基苯酚;醇/氧化烯加成產物,如乙氧基化十三烷醇;皂,如硬脂酸鈉;烷基萘磺酸酯的鹽,如二丁基萘磺酸鈉;磺基琥珀酸二烷基酯的鹽,如二(2-乙基己基)磺基琥珀酸鈉;山梨糖醇酯,如山梨糖醇油酸酯;季胺,如氯化十二烷基三甲基銨;脂肪酸的聚乙二醇酯,如聚乙二醇硬脂酸酯;環氧乙烷和環氧丙烷的嵌段共聚物;以及磷酸單烷基酯和二烷基酯的鹽;以及還有另外的物質,例如描述於:McCutcheon's Detergents and Emulsifiers Annual [麥卡琴清潔劑和乳化劑年鑒],MC出版公司(MC Publishing Corp.),裡奇伍德,新澤西州(Ridgewood New Jersey)(1981)。
可以用於殺有害生物配製物的另外的佐劑包括結晶抑制劑、黏度調節劑、懸浮劑、染料、抗氧化劑、發泡劑、光吸收劑、混合助劑、消泡劑、錯合劑、中和或改變pH的物質和緩衝液、腐蝕抑制劑、香料、濕潤劑、吸收增強劑、微量營養素、塑化劑、助流劑、潤滑劑、分散劑、增稠劑、防凍劑、殺微生物劑、以及液體和固體肥料。
根據本發明之組成物可以包括添加劑,該添加劑包括植物或動物來源的油、礦物油、此類油的烷基酯或此類油與油衍生物的混合物。在根據本發明之組成物中的油添加劑的量通常是基於該待施用的混合物的從0.01%到10%。例如,可以在噴霧混合物已經製備之後將該油添加劑以所希望的濃度添加到噴霧罐中。較佳的油添加劑包括礦物油或植物來源的油,例如菜籽油、橄欖油或葵花籽油;乳化的植物油;植物來源的油的烷基酯,例如甲基衍生物;或動物來源的油,如魚油或牛脂。較佳的油添加劑包括C
8-C
22脂肪酸的烷基酯,尤其是C
12-C
18脂肪酸的甲基衍生物,例如月桂酸、棕櫚酸以及油酸的甲基酯(分別為月桂酸甲酯、棕櫚酸甲酯和油酸甲酯)。許多油衍生物獲知於Compendium of Herbicide Adjuvants[除草劑佐劑綱要],第10版,南伊利諾大學,2010。
除草組成物總體上包含按重量計從0.1%至99%、尤其是按重量計從0.1%至95%的具有式 (I) 的化合物和按重量計從1%至99.9%的配製佐劑,該配製佐劑較佳的是包括按重量計從0至25%的表面活性物質。本發明組成物總體上包括按重量計從0.1%至99%、尤其是按重量計從0.1%至95%的本發明之化合物以及按重量計從1%至99.9%的配製佐劑,該配製佐劑較佳的是包括按重量計從0至25%的表面活性物質。而商業產品可以較佳的是被配製為濃縮物,最終使用者將通常使用稀釋配製物。
施用比率在寬範圍之內變化並且取決於土壤的性質、施用方法、作物植物、待控制的有害生物、主要氣候條件、以及受施用方法、施用時間以及目標作物支配的其他因素。一般來講,可以將化合物以從1 l/ha至2000 l/ha、尤其是從10 l/ha到1000 l/ha的比率施用。
較佳的配製物可以具有以下組成(重量%):
可乳化的濃縮物:
活性成分: 1%至95%,較佳的是60%至90%
表面活性劑: 1%至30%,較佳的是5%至20%
液體載劑: 1%至80%,較佳的是1%至35%
粉塵劑:
活性成分: 0.1%至10%,較佳的是0.1%至5%
固體載劑: 99.9%至90%,較佳的是99.9%至99%
懸浮液濃縮物:
活性成分: 5%至75%,較佳的是10%至50%
水: 94%至24%,較佳的是88%至30%
表面活性劑: 1%至40%,較佳的是2%至30%
可濕性粉劑:
活性成分: 0.5%至90%,較佳的是1%至80%
表面活性劑: 0.5%至20%,較佳的是1%至15%
固體載劑: 5%至95%,較佳的是15%至90%
顆粒劑:
活性成分: 0.1%至30%,較佳的是0.1%至15%
固體載劑: 99.5%至70%,較佳的是97%至85%
本發明之組成物可以進一步包含至少一種另外的殺有害生物劑。例如,根據本發明之化合物也可以與其他除草劑或植物生長調節劑組合使用。在較佳的實施方式中,該另外的殺有害生物劑係除草劑和/或除草劑安全劑。
本發明之化合物還可以與一種或多種額外的除草劑和/或植物生長調節劑混合使用。此類另外的除草劑或植物生長調節劑的實例包括乙草胺、三氟羧草醚(包括三氟羧草醚-鈉)、苯草醚、莠滅淨、胺唑草酮、氯胺吡啶酸、殺草強、莠去津、氟丁醯草胺-M、喹草酮(benquitrione)、苄嘧磺隆(包括苄嘧磺隆-甲基)、滅草松、二環哌喃酮、雙丙胺膦、雙唑草酮、雙草醚-鈉、比克羅腙(bixlozone)、除草定、溴苯腈、丁草胺、氟丙嘧草酯、唑草酮(包括唑草酮-乙基)、氯酯磺草胺(包括氯酯磺草胺-甲基)、氯嘧磺隆(包括氯嘧磺隆-乙基)、綠麥隆、氯磺隆、環庚草醚、氯醯草膦(clacyfos)、烯草酮、炔草酸(包括炔草酯)、異㗁草酮、二氯吡啶酸、環吡拉尼(cyclopyranil)、環吡瑞莫(cyclopyrimorate)、環丙嘧磺隆、氰氟草酯(包括氰氟草酯-丁基)、2,4-D(包括其膽鹼鹽和2-乙基己基酯)、2,4-DB、甜菜安、麥草畏(包括其鋁、胺基丙基、雙-胺基丙基甲基、膽鹼、二氯丙、二甘醇胺、二甲胺、二甲基銨、鉀鹽和鈉鹽)、雙氯磺草胺、吡氟醯草胺、氟吡草腙、二甲草胺、精二甲吩草胺、雙側氧基吡硫翁(dioxopyritrione)、二溴敵草快、敵草隆、依吡非那西爾(epyrifenacil)、乙丁烯氟靈、乙氧呋草黃、㗁唑禾草靈(包括精㗁唑禾草靈-乙基)、苯磺㗁唑草(fenoxasulfone)、苯唑氟草酮、芬奎崔頓(fenquinotrione)、四唑醯草胺、啶嘧磺隆、雙氟磺草胺、氯氟吡啶酯(florpyrauxifen)(包括氯氟吡啶酯-苄基)、吡氟禾草靈(包括精吡氟禾草靈-丁基)、氟酮磺隆(包括氟酮磺隆-鈉)、氟噻草胺、唑嘧磺草胺、丙炔氟草胺、氟草隆、氟磺胺草醚、氟啶嘧磺隆(包括氟啶嘧磺隆-甲基-鈉)、氟草煙(包括氯氟吡氧乙酸(fluroxypyr-meptyl))、氟黃胺草醚、甲醯胺磺隆、草銨膦(包括L-草銨膦和兩者的銨鹽)、草甘膦(包括其二銨、異丙基銨和鉀鹽)、氟氯吡啶酯(halauxifen)(包括氟氯吡啶酯-甲基)、氟吡甲禾靈(包括氟吡甲禾靈-甲基)、環𠯤酮、乙內醯脲啶(hydantocidin)、甲氧咪草煙(包括R-甲氧咪草煙)、甲咪唑菸酸、滅草煙、咪草煙、茚𠯤氟草胺、碘甲磺隆(包括碘甲磺隆-甲基-鈉)、碘芬磺隆(iofensulfuron)(包括碘芬磺隆-鈉)、碘苯腈、異丙隆、異㗁唑草酮、蘭柯三酮(lancotrione)、MCPA、MCPB、高二甲四氯丙酸(mecoprop-P)、甲基二磺隆(包括甲基二磺隆-甲基)、甲基磺草酮、苯𠯤草酮、吡草胺、異㗁噻草醚(methiozolin)、異丙甲草胺、磺草唑胺、𠯤草酮、甲磺隆、敵草胺、煙嘧磺隆、達草滅、㗁草酮、環氧嘧磺隆、乙氧氟草醚、二氯化百草枯、二甲戊樂靈、五氟磺草胺、苯敵草、毒莠定、唑啉草酯、丙草胺、氟嘧磺隆-甲基、撲草淨、敵稗、喔草酯、丙𠯤嘧磺隆(propyrisulfuron)、戊炔草胺、苄草丹、氟磺隆、雙唑草腈、吡草醚(pyraflufen)(包括吡草醚-乙基)、磺醯草吡唑、噠草特、環酯草醚、吡丙醚(pyrimisulfan)、吡咯磺隆(pyroxasulfone)、啶磺草胺、二氯喹啉酸、氯甲喹啉酸、喹禾靈(包括精喹禾靈-乙基和喹禾糠酯(quizalofop-P-tefuryl))、利米沙芬(rimisoxafen)、碸嘧磺隆、嘧啶肟草醚、烯禾啶、西瑪津、精異丙甲草胺、甲磺草胺、磺醯磺隆、丁噻隆、特呋三酮、環磺酮、特丁津、特丁淨、四氟絡草胺(tetflupyrolimet)、噻酮磺隆(thiencarbazone)、噻吩磺隆、氟嘧硫草酯(tiafenacil)、托比利特(tolpyralate)、苯吡唑草酮、三甲苯草酮、氟酮磺草胺(triafamone)、野麥畏、醚苯磺隆、苯磺隆(包括苯磺隆-甲基)、綠草定、三氟啶磺隆(包括三氟啶磺隆-鈉)、三氟草𠯤(trifludimoxazin)、氟樂靈、氟胺磺隆、三唑磺草酮、[(E)-[2-(三氟甲基)苯基]亞甲基胺基]2,6-雙[(4,6-二甲氧基嘧啶-2-基)氧基]苯甲酸酯、3-(2-氯-4-氟-5-(3-甲基-2,6-二側氧基-4-三氟甲基-3,6-二氫嘧啶-1(2H)-基)苯基)-5-甲基-4,5-二氫異㗁唑-5-甲酸乙酯、4-羥基-1-甲氧基-5-甲基-3-[4-(三氟甲基)-2-吡啶基]咪唑啶-2-酮、4-羥基-1,5-二甲基-3-[4-(三氟甲基)-2-吡啶基]咪唑啶-2-酮、5-乙氧基-4-羥基-1-甲基-3-[4-(三氟甲基)-2-吡啶基]咪唑啶-2-酮、4-羥基-1-甲基-3-[4-(三氟甲基)-2-吡啶基]咪唑啶-2-酮、4-羥基-1,5-二甲基-3-[1-甲基-5-(三氟甲基)吡唑-3-基]咪唑啶-2-酮、(4R)1-(5-三級丁基異㗁唑-3-基)-4-乙氧基-5-羥基-3-甲基-咪唑啶-2-酮、4-胺基-3-氯-5-氟-6-(7-氟-1H-吲哚-6-基)吡啶-2-甲酸(包括其農用化學上可接受的酯,例如,4-胺基-3-氯-5-氟-6-(7-氟-1H-吲哚-6-基)吡啶-2-甲酸甲酯、4-胺基-3-氯-5-氟-6-(7-氟-1H-吲哚-6-基)吡啶-2-甲酸丙-2-炔基酯和4-胺基-3-氯-5-氟-6-(7-氟-1H-吲哚-6-基)吡啶-2-甲酸氰甲酯)、3-乙基氫硫基-N-(1,3,4-㗁二唑-2-基)-5-(三氟甲基)-[1,2,4]三唑并[4,3-a]吡啶-8-甲醯胺、3-(異丙基氫硫基甲基)-N-(5-甲基-1,3,4-㗁二唑-2-基)-5-(三氟甲基)-[1,2,4]三唑并[4,3-a]吡啶-8-甲醯胺、3-(異丙基磺醯基甲基)-N-(5-甲基-1,3,4-㗁二唑-2-基)-5-(三氟甲基)-[1,2,4]三唑并[4,3-a]吡啶-8-甲醯胺、3-(乙基磺醯基甲基)-N-(5-甲基-1,3,4-㗁二唑-2-基)-5-(三氟甲基)-[1,2,4]三唑并[4,3-a]吡啶-8-甲醯胺、2-[[3-[[3-氯-5-氟-6-[3-甲基-2,6-二側氧基-4-(三氟甲基)嘧啶-1-基]-2-吡啶基]氧基]乙酸乙酯、6-氯-4-(2,7-二甲基-1-萘基)-5-羥基-2-甲基-嗒𠯤-3-酮、(2R)-2-[(4-胺基-3,5-二氯-6-氟-2-吡啶基)氧基]丙酸四氫呋喃-2-基甲基酯、(2R)-2-[(4-胺基-3,5-二氯-6-氟-2-吡啶基)氧基]丙酸、2-[(4-胺基-3,5-二氯-6-氟-2-吡啶基)氧基]丙酸四氫呋喃-2-基甲基酯、2-[(4-胺基-3,5-二氯-6-氟-2-吡啶基)氧基]丙酸、2-氟-N-(5-甲基-1,3,4-㗁二唑-2-基)-3-[(R)-丙基亞磺醯基]-4-(三氟甲基)苯甲醯胺、2-氟-N-(5-甲基-1,3,4-㗁二唑-2-基)-3-丙基亞磺醯基-4-(三氟甲基)苯甲醯胺、6-胺基-5-氯-2-(4-氯-2-氟-3-甲氧基-苯基)嘧啶-4-甲酸(2-氟苯基)甲基酯、6-胺基-5-氯-2-(4-氯-2-氟-3-甲氧基-苯基)嘧啶-4-甲酸、3-(3-氯苯基)-6-(5-羥基-1,3-二甲基-吡唑-4-羰基)-1,5-二甲基-喹唑啉-2,4-二酮、以及[4-[3-(3-氯苯基)-1,5-二甲基-2,4-二側氧基-喹唑啉-6-羰基]-2,5-二甲基-吡唑-3-基]N,N-二乙基胺基甲酸酯、2-[(E)-[2-氯-4-氟-5-[3-甲基-2,6-二側氧基-4-(三氟甲基)嘧啶-1-基]苯基]亞甲基胺基]氧基丙酸甲酯、以及(2R)-2-[(E)-[2-氯-4-氟-5-[3-甲基-2,6-二側氧基-4-(三氟甲基)嘧啶-1-基]苯基]亞甲基胺基]氧基丙酸甲酯。
具有式 (I) 的化合物的混合配伍物還可以呈酯或鹽的形式,如例如在以下文獻中所提到的:The Pesticide Manual [殺有害生物劑手冊], 第十四版, British Crop Protection Council [英國作物保護委員會], 2006。
具有式 (I) 的化合物還可以在與其他農用化學品(如殺真菌劑、殺線蟲劑或殺昆蟲劑)的混合物中使用,該等農用化學品的實例在殺有害生物劑手冊中給出。
具有式 (I) 的化合物與混合配伍物的混合比較佳的是係從1 : 100至1000 : 1。
該等混合物可以有利地用於以上提到的該等配製物中(在這種情況下「活性成分」涉及具有式 (I) 的化合物與混合配伍物的對應混合物)。
本發明之具有式 (I) 的化合物也可以與除草劑安全劑組合。較佳的組合為解草𠯤、解草酯(cloquintocet)(包括解毒喹)、環丙磺醯胺、二氯丙烯胺、解草唑(包括解草唑-乙基)、解草啶、氟草肟、解草㗁唑、雙苯㗁唑酸(包括雙苯㗁唑酸-乙基)、吡唑解草酸(mefenpyr)(包括吡唑解草酸-二乙基)、除草劑安全劑(metcamifen)和解草腈。
特別較佳的是具有式 (I) 的化合物與環丙磺醯胺、雙苯㗁唑酸(包括雙苯㗁唑酸-乙基)、解草酯(包括解草喹)和/或N-(2-甲氧基苯甲醯基)-4-[(甲基-胺基羰基)胺基]苯磺醯胺的混合物。
具有式 (I) 的化合物的該等安全劑還可以處於酯或鹽的形式,例如像在《殺有害生物劑手冊》(第14版(BCPC),2006)中所提及的。提及解草喹還適用於其鋰、鈉、鉀、鈣、鎂、鋁、鐵、銨、季銨、鋶或鏻鹽(如在WO 02/34048中揭露的),並且對解草唑-乙基的提及還適用於解草唑,等。
較佳的是,具有式 (I) 的化合物與安全劑的混合比係從100 : 1至1 : 10,尤其是從20 : 1至1 : 1。
該等混合物可有利地用於以上提到的配製物中(在這種情況下「活性成分」涉及具有式 (I) 的化合物與安全劑的對應混合物)。
本發明之具有式 (I) 的化合物作為除草劑係有用的。因此,本發明進一步包括用於控制不想要的植物之方法,包括向該植物或包含它們的場所施用有效量的本發明化合物或含有該化合物的除草組成物。‘控制’意指殺死、減少或延遲生長或預防或減少發芽。通常有待控制的植物係不想要的植物(雜草)。‘場所’意指植物在其中正生長或將生長的區域。
具有式 (I) 的化合物的施用比率可以在寬的限度內變化並且取決於土壤的性質、施用之方法(出苗前;出苗後;施用於種子溝;免耕法施用等)、作物植物、待控制的一種或多種雜草、當時的氣候條件和其他受施用方法、施用時間和目標作物支配的因素。根據本發明之具有式 (I) 的化合物通常以從10 g/ha至2000 g/ha,尤其是從50 g/ha到1000 g/ha的比率施用。較佳的範圍為10-200 g/ha。
通常藉由噴灑該組成物進行施用,典型地是藉由用於大面積的裝在拖拉機上的噴灑機,但是還可以使用其他方法如撒粉(針對粉末)、滴加或浸灌。
可以使用根據本發明之組成物的有用植物包括作物如穀物,例如大麥和小麥、棉花、油菜籽油菜、向日葵、玉米、稻、大豆、甜菜、甘蔗以及草皮。
作物植物還可以包括樹,如果樹、棕櫚樹、椰子樹或其他堅果。還包括藤本植物(如葡萄)、灌木果樹、果實植物和蔬菜。
作物應被理解為還包括藉由常規的育種方法或藉由基因工程已經賦予對除草劑或多種類別的除草劑(例如ALS-抑制劑、GS-抑制劑、EPSPS-抑制劑、PPO-抑制劑、ACC酶-抑制劑和HPPD-抑制劑)的耐受性的那些作物。藉由常規的育種方法已經賦予對咪唑啉酮(例如,甲氧咪草煙)的耐受性的作物的實例係Clearfield®夏季油菜(卡諾拉(canola))。藉由基因工程方法已經賦予對除草劑的耐受性的作物的實例包括例如具有草甘膦和草銨膦抗性的玉米品種,該等玉米品種在RoundupReady®和LibertyLink®商標名下是可商購的。
農作物還應理解為藉由基因工程方法已經賦予其對有害昆蟲有抗性的那些農作物,例如Bt玉米(對歐洲玉米螟有抗性)、Bt棉花(對棉鈴象鼻蟲有抗性)和還有Bt馬鈴薯(對科羅拉多甲蟲有抗性)。Bt玉米的實例係NK®的Bt 176玉米雜交體(先正達種子公司(Syngenta Seeds))。Bt毒素係由蘇雲金芽孢桿菌(
Bacillus thuringiensis)土壤細菌天然形成的蛋白質。毒素或能夠合成此類毒素的轉基因植物的實例被描述在EP-A-451 878、EP-A-374 753、WO 93/07278、WO 95/34656、WO 03/052073和EP-A-427 529中。包含一個或多個編碼殺昆蟲抗性和表現一種或多種毒素的基因的轉基因植物的實例係KnockOut®(玉米)、Yield Gard®(玉米)、NuCOTIN33B®(棉花)、Bollgard®(棉花)、NewLeaf®(馬鈴薯)、NatureGard®以及Protexcta®。植物作物或其種子材料均可以是抗除草劑的並且同時係抗昆蟲攝食的(「疊加的」轉基因結果)。例如,種子可以具有表現殺昆蟲的Cry3蛋白的能力,而同時對草甘膦係耐受的。
作物還應被理解為包括藉由常規育種方法或基因工程獲得並且含有所謂輸出性狀(例如改進的儲存穩定性、更高的營養價值以及改進的香味)的那些作物。
其他有用的植物包括例如在高爾夫球場、草地、公園以及路旁的或者商業上種植用於草地的草皮草,以及觀賞植物,如花卉或灌木。
本發明之具有式 (I) 的化合物和組成物通常可以用於控制多種單子葉和雙子葉雜草物種。典型地可以被控制的單子葉物種的實例包括大穗看麥娘(
Alopecurus myosuroides)、野燕麥(
Avena fatua)、車前臂形草(
Brachiaria plantaginea)、旱雀麥(
Bromus tectorum)、油莎草(
Cyperus esculentus)、馬唐(
Digitaria sanguinalis)、稗草(
Echinochloa crus-galli)、多年生黑麥草(
Lolium perenn)、多花黑麥草(
Lolium multiflorum)、黍稷(
Panicum miliaceum )、一年生早熟禾( Poa annua )、狗尾草( Setaria viridis )、大狗尾草( Setaria faberi )和兩色蜀黍( Sorghum bicolor )。可以被控制的雙子葉物種的實例包括:苘麻(
Abutilon theophrasti)、反枝莧(
Amaranthus retroflexus)、鬼針草、藜草(
Chenopodium album)、白苞猩猩草、豬殃殃、牽牛花、地膚(
Kochia scoparia)、卷莖蓼(
Sinapis arvensis)、刺金午時花(
Sida spinosa)、新疆野生油菜(
Sinapis arvensis)、龍葵、繁縷(
Stellaria media)、波斯婆婆納(
Veronica persica)和蒼耳(
Xanthium strumarium)。
不想要的植物應被理解為還包括藉由進化、藉由常規的育種方法或藉由基因工程已經賦予對除草劑或多種類別的除草劑(例如ALS-抑制劑、GS-抑制劑、EPSPS-抑制劑、PPO-抑制劑、ACC酶-抑制劑和HPPD-抑制劑)的耐受性的那些雜草。實例包括已經進化而具有對於草甘膦和/或乙醯乳酸合酶(ALS)抑制除草劑的抗性的長芒莧(Amaranthus palmeri)。
本發明之化合物可以用於控制具有對於原紫質原氧化酶(PPO)抑制劑的抗性的不想要的植物或雜草之方法中。例如,由於PPX2L中的胺基酸取代,如在胺基酸R128(也稱為R98)和G399處發生的取代,或者PPX2L中在密碼子210(Δ210)處的密碼子(甘胺酸)缺失,長芒莧和糙果莧種群已經進化為抗PPO雜草,密碼子編號係基於NCBI參考序列DQ386114。本發明之化合物可以用於控制具有前面提及的密碼子或等價物處的突變或缺失的長芒莧和/或糙果莧之方法中,並且明顯的是嘗試用該等化合物控制具有可能出現的賦予對於PPO抑制劑的耐受性或抗性的其他突變的不想要的植物或雜草。
具有式 (I) 的化合物也可用於作物收穫前乾燥,例如但不限於馬鈴薯、大豆、向日葵和棉花。收穫前乾燥用於乾燥作物葉片,而不會對作物本身造成顯著損害,以幫助收穫。
本發明之化合物/組成物特別可用於非選擇性燃盡(burn-down)應用,並且因此也可用於控制自生自長(volunteer)或逃逸作物(escape crop)植物。
現在將藉由舉例更詳細地說明本發明之不同方面和實施方式。應當理解的是,在不偏離本發明範圍的情況下,可以對細節做出修改。
實施例
以下實施例用來說明但不限制本發明。
合成實施例 實施例 1 (3- 甲氧基 -3- 側氧基 - 丙基 )2-[2- 氯 -5-(3,5- 二甲基 -2,6- 二側氧基 -4- 硫酮基 -1,3,5- 三 𠯤 烷 -1- 基 )-4- 氟 - 苯基 ] 氫硫基丙酸酯(化合物 9-245 )的製備 步驟 1 :2-氯-4-氟-5-硝基-苯甲酸的合成
在0°C下將發煙硝酸(2.8 ml,43 mmol)添加至2-氯-4-氟-苯甲酸(5.0 g,29 mmol)在濃硫酸(20 ml)中的攪拌溶液中。將混合物攪拌20分鐘,然後將其小心地倒入冰水中。將所得混合物過濾,並且用乙腈清洗固體,以提供2-氯-4-氟-5-硝基-苯甲酸(6.4 g)。
1H NMR (400 MHz, CDCl
3) δ 8.6 (d,1H), 7.05 (d,1H), 5.9 (br s,1H) ppm。
步驟 2 :2-氯-4-氟-5-硝基-苯甲酸乙酯的合成
將草醯氯(0.88 ml,9.9 mmol)逐滴添加至2-氯-4-氟-5-硝基-苯甲酸(1.5 g,6.6 mmol)在二氯甲烷(15 ml)中的溶液中。將溶液攪拌15分鐘,然後添加二甲基甲醯胺(3滴)並持續攪拌,直至停止釋放氣體。添加乙醇(4 ml,67 mmol),並且將所得溶液攪拌17小時,然後在減壓下蒸發溶劑,以提供呈固體的2-氯-4-氟-5-硝基-苯甲酸乙酯(1.7 g)。
1H NMR (400 MHz, CDCl
3) δ 8.7 (d,1H), 7.5 (d,1H), 4.45 (q,2H), 1.45 (t, 3H) ppm。
步驟 3 :5-胺基-2-氯-4-氟-苯甲酸乙酯的合成
將二氯化錫水合物(4.7 g,24 mmol)添加至2-氯-4-氟-5-硝基-苯甲酸乙酯(2.1 g,8.1 mmol)在乙酸乙酯(21 ml)中的攪拌溶液中,然後將混合物在回流下加熱1.5小時,將其冷卻並且在減壓下蒸發溶劑。將殘餘物藉由管柱層析法純化,以提供5-胺基-2-氯-4-氟-苯甲酸乙酯(1.2 g)。
1H NMR (400 MHz, CDCl
3) δ 7.3 (d,1H), 7.1 (d,1H), 4.35 (q,2H), 3.35 (br s, 2H), 1.4 (t, 3H) ppm。
步驟 4 :2-氯-4-氟-5-異氰酸基-苯甲酸乙酯的合成
將雙光氣(0.8 ml,6.6 mmol)添加到5-胺基-2-氯-4-氟-苯甲酸乙酯(1.2 g,5.5 mmol)在乾燥甲苯(24 ml)中的攪拌溶液中。將所得混合物在回流下加熱2小時,將其冷卻並在減壓下濃縮,以提供2-氯-4-氟-5-異氰酸基-苯甲酸乙酯。
步驟 5 :2-氯-5-(3,5-二甲基-2,6-二側氧基-4-硫酮基-1,3,5-三𠯤烷-1-基)-4-氟-苯甲酸乙酯的合成
將1,3-二甲基硫脲(0.26 g,2.5 mmol)和三乙胺(0.37 ml,2.7 mmol)在甲苯(10 ml)中的溶液添加到2-氯-4-氟-5-異氰酸基-苯甲酸乙酯(500 mg,2.1 mmol)中,並將所得溶液加熱至回流。在15分鐘內分批添加羰基二咪唑(520 mg,3.1 mmol),並將所得溶液在回流下再加熱3小時,然後將其冷卻並在減壓下蒸發溶劑。將殘餘物藉由管柱層析法純化,以提供呈膠狀物的2-氯-5-(3,5-二甲基-2,6-二側氧基-4-硫酮基-1,3,5-三𠯤烷-1-基)-4-氟-苯甲酸乙酯(550 mg)。
1H NMR (400 MHz, CDCl
3) δ 7.95 (d,1H), 7.45 (d,1H), 4.4 (q,2H), 3.8 (s, 6H), 1.45 (t, 3H) ppm。
步驟 6 :2-氯-5-(3,5-二甲基-2,6-二側氧基-4-硫酮基-1,3,5-三𠯤烷-1-基)-4-氟-苯甲酸的合成
將濃硫酸(2.6 ml,45 mmol)添加至2-氯-5-(3,5-二甲基-2,6-二側氧基-4-硫酮基-1,3,5-三𠯤烷-1-基)-4-氟-苯甲酸乙酯(1.7 g,4.5 mmol)在冰乙酸(17 ml)中的攪拌溶液中。將混合物在110°C下加熱6小時,將其冷卻至環境溫度,並小心地倒入冰水中。將所得混合物過濾,並將固體乾燥,以提供2-氯-5-(3,5-二甲基-2,6-二側氧基-4-硫酮基-1,3,5-三𠯤烷-1-基)-4-氟-苯甲酸(1.5 g)。
1H NMR (400 MHz, DMSO-d
6) δ 8.15 (d,1H), 7.85 (d,1H), 3.6 (s, 6H), 3.35 (br s, 1H) ppm。
步驟 7 : N-[2-氯-5-(3,5-二甲基-2,6-二側氧基-4-硫酮基-1,3,5-三𠯤烷-1-基)-4-氟-苯基]胺基甲酸三級丁酯的合成
將二環己基碳二亞胺(0.64 g,3.0 mmol)在氯苯(6 ml)中的溶液逐滴添加到2-氯-5-(3,5-二甲基-2,6-二側氧基-4-硫酮基-1,3,5-三𠯤烷-1-基)-4-氟-苯甲酸(1.0 g,2.9 mmol)和
N-羥基胺基甲酸三級丁酯(0.37 g,2.7 mmol)在氯苯(6 ml)中的在-15°C下的攪拌溶液中。將所得混合物攪拌30分鐘,然後添加二氯化鈀三苯基膦錯合物(0.1 g,0.15 mmol)和碳酸銫(1.9 g,5.8 mmol),並且將混合物在85°C下加熱一小時。將混合物冷卻,用乙酸乙酯萃取,並且將有機相乾燥並蒸發,以留下殘餘物,將該殘餘物藉由管柱層析法純化,以提供
N-[2-氯-5-(3,5-二甲基-2,6-二側氧基-4-硫酮基-1,3,5-三𠯤烷-1-基)-4-氟-苯基]胺基甲酸三級丁酯(0.8 g)。
1H NMR (400 MHz, CDCl
3) δ 8.3 (d,1H), 7.3 (d,1H), 3.8 (s, 6H), 1.5 (s, 9H) ppm (未觀察到NH)。
步驟 8 :3-(5-胺基-4-氯-2-氟-苯基)-1,5-二甲基-6-硫酮基-1,3,5-三𠯤烷-2,4-二酮的合成
將
N-[2-氯-5-(3,5-二甲基-2,6-二側氧基-4-硫酮基-1,3,5-三𠯤烷-1-基)-4-氟-苯基]胺基甲酸三級丁酯(700 mg,1.7 mmol)和三氟乙酸(10.5 ml)的混合物在環境溫度下攪拌1小時,然後在減壓下濃縮。添加飽和碳酸氫鈉水溶液(30 ml),並將混合物用乙酸乙酯(2 × 80 ml)萃取。將合併的有機相經硫酸鈉乾燥、過濾並在減壓下蒸發,以提供呈白色固體的3-(5-胺基-4-氯-2-氟-苯基)-1,5-二甲基-6-硫酮基-1,3,5-三𠯤烷-2,4-二酮(500 mg)。
1H NMR (400 MHz, CDCl
3) δ 7.25 (d,1H), 6.7 (d,1H), 3.8 (s, 6H) ppm (未觀察到NH
2)。
步驟 9 :2-氯-5-(3,5-二甲基-2,6-二側氧基-4-硫酮基-1,3,5-三𠯤烷-1-基)-4-氟-苯磺醯氯的合成
將亞硝酸鈉(0.24 g,3.3 mmol)在水(12 ml)中的在0°C下的溶液逐滴添加到3-(5-胺基-4-氯-2-氟-苯基)-1,5-二甲基-6-硫酮基-1,3,5-三𠯤烷-2,4-二酮(0.9 g,2.8 mmol)和鹽酸(24 ml)在-5°C下的攪拌的混合物中,並且將所得混合物在0°C下攪拌15分鐘。將該混合物逐滴添加到氯化亞碸(12 ml)和水(48 ml)的攪拌的混合物中,在該混合物中,已在-5°C下添加有氯化銅 (I)(6 mg,0.06 mmol)。將所得混合物在0°C下攪拌30分鐘並在環境溫度下攪拌1小時,然後添加水(30 ml)和乙酸乙酯(90 ml)。分離相,並用乙酸乙酯(90 ml)萃取水相。將合併的有機相經硫酸鈉乾燥、過濾並在減壓下蒸發,以提供呈固體的2-氯-5-(3,5-二甲基-2,6-二側氧基-4-硫酮基-1,3,5-三𠯤烷-1-基)-4-氟-苯磺醯氯(1 g)。
1H NMR (400 MHz, CDCl
3) δ 8.2 (d,1H), 7.6 (d,1H), 3.8 (s, 6H) ppm。
步驟 10 :3-(4-氯-2-氟-5-氫硫基-苯基)-1,5-二甲基-6-硫酮基-1,3,5-三𠯤烷-2,4-二酮的合成
將三苯基膦(0.94 g,3.5 mmol)分批添加到2-氯-5-(3,5-二甲基-2,6-二側氧基-4-硫酮基-1,3,5-三𠯤烷-1-基)-4-氟-苯磺醯氯(0.5 g,1.0 mmol)在四氫呋喃(6 ml)中的攪拌溶液中。添加水(1 ml),並將所得混合物在環境溫度下攪拌18小時。添加水(20 ml)和乙酸乙酯(50 ml),並分離相。用乙酸乙酯(50 ml)萃取水相,並將合併的有機相經硫酸鈉乾燥、過濾並在減壓下蒸發,以留下殘餘物,將該殘餘物藉由管柱層析法純化,以提供呈固體的3-(4-氯-2-氟-5-氫硫基-苯基)-1,5-二甲基-6-硫酮基-1,3,5-三𠯤烷-2,4-二酮(264 mg)。
1H NMR (400 MHz, CDCl
3) δ 7.35 (m,2H), 3.9 (s,1H), 3.8 (s, 6H) ppm。
步驟 11 :(3-甲氧基-3-側氧基-丙基)2-[2-氯-5-(3,5-二甲基-2,6-二側氧基-4-硫酮基-1,3,5-三𠯤烷-1-基)-4-氟-苯基]氫硫基丙酸酯(化合物9-245)的合成
將(3-甲氧基-3-側氧基-丙基)2-溴丙酸酯(如在實施例2中所述製備;70 mg,0.29 mmol)添加到3-(4-氯-2-氟-5-氫硫基-苯基)-1,5-二甲基-6-硫酮基-1,3,5-三𠯤烷-2,4-二酮(90 mg,0.26 mmol)、碳酸銫(88 mg,0.27 mmol)和乙腈(1.8 ml)的攪拌的混合物中,並將所得混合物在環境溫度下攪拌2小時。添加乙酸乙酯(40 ml),並將所得混合物用水(2 × 10 ml)清洗、經硫酸鈉乾燥、過濾並蒸發,以留下殘餘物,將該殘餘物藉由管柱層析法純化,以提供呈油狀物的(3-甲氧基-3-側氧基-丙基)2-[2-氯-5-(3,5-二甲基-2,6-二側氧基-4-硫酮基-1,3,5-三𠯤烷-1-基)-4-氟-苯基]氫硫基丙酸酯(化合物9-245)(85 mg)。
1H NMR (400 MHz, CDCl
3) δ 7.55 (d,1H), 7.4 (d, 1H), 4.3 (m, 2H), 3.9 (m, 1H), 3.75 (s, 6H), 3.65 (s, 3H), 2.6 (m, 2H), 1.55 (d, 3H) ppm。
實施例 2 (3- 甲氧基 -3- 側氧基 - 丙基 )2- 溴丙酸酯的製備
將三乙胺(1.3 ml,9.1 mmol)和3-羥基丙酸甲酯(0.48 ml,5.0 mmol)逐滴添加到2-溴丙醯溴(0.49 ml,4.5 mmol)在乙腈(15 ml)中的在0°C下的攪拌溶液中。將所得混合物在0°C下攪拌1小時,然後在環境溫度下攪拌2小時。添加水(20 ml)和乙酸乙酯(60 ml),分離相,並用乙酸乙酯(60 ml)萃取水相。將合併的有機相經硫酸鈉乾燥、過濾並在減壓下蒸發,以留下油狀物,將該油狀物藉由管柱層析法純化,以提供呈油狀物的(3-甲氧基-3-側氧基-丙基)2-溴丙酸酯(440 mg)。
1H NMR (400 MHz, CDCl
3) δ 4.45 (m, 2H), 4.35 (m, 1H), 3.75 (s, 3H), 2.7 (t, 2H), 1.8 (d, 3H) ppm。
實施例 3 3-[2-[2- 氯 -5-(3,5- 二甲基 -2,6- 二側氧基 -4- 硫酮基 -1,3,5- 三 𠯤 烷 -1- 基 )-4- 氟 - 苯基 ] 氫硫基丙醯基胺基 ] 丙酸甲酯(化合物 9-272 )的製備 步驟 1 :3-(2-溴丙醯基胺基)丙酸甲酯的合成
將三乙胺(2.6 ml,9.1 mmol)和2-溴丙醯溴(0.97 ml,9.1 mmol)添加到(3-甲氧基-3-側氧基-丙基)氯化銨(1.42 g,10 mmol)在乙腈(30 ml)中的在0°C下的攪拌的混合物中。將所得混合物在0°C下攪拌1小時,然後在環境溫度下攪拌2小時。添加水(20 ml)和乙酸乙酯(60 ml),分離相,並用乙酸乙酯(60 ml)萃取水相。將合併的有機相經硫酸鈉乾燥、過濾並在減壓下蒸發,以留下油狀物,將該油狀物藉由管柱層析法純化,以提供呈固體的3-(2-溴丙醯基胺基)丙酸甲酯(560 mg)。
1H NMR (400 MHz, CDCl
3) δ 6.95 (br s, 1H), 4.4 (q, 1H), 3.75 (s, 3H), 3.55 (m, 2H), 2.6 (m, 2H), 1.85 (d, 3H) ppm。
步驟 2 :3-[2-[2-氯-5-(3,5-二甲基-2,6-二側氧基-4-硫酮基-1,3,5-三𠯤烷-1-基)-4-氟-苯基]氫硫基丙醯基胺基]丙酸甲酯(化合物9-272)的合成
將3-(2-溴丙醯基胺基)丙酸甲酯(78 mg,0.32 mmol)添加到3-(4-氯-2-氟-5-氫硫基-苯基)-1,5-二甲基-6-硫酮基-1,3,5-三𠯤烷-2,4-二酮(如在實施例1、步驟10中所述製備;100 mg,0.29 mmol)、碳酸銫(98 mg,0.30 mmol)和乙腈(2 ml)的攪拌的混合物中,並將所得混合物在環境溫度下攪拌2小時。添加乙酸乙酯(50 ml),並將所得混合物用水(2 × 20 ml)清洗、經硫酸鈉乾燥、過濾並蒸發,以留下殘餘物,將該殘餘物藉由管柱層析法純化,以提供呈固體的3-[2-[2-氯-5-(3,5-二甲基-2,6-二側氧基-4-硫酮基-1,3,5-三𠯤烷-1-基)-4-氟-苯基]氫硫基丙醯基胺基]丙酸甲酯(化合物9-272)(36 mg)。
1H NMR (400 MHz, CDCl
3) δ 7.35 (d, 1H), 7.25 (d, 1H), 7.0 (br m, 1H), 3.8 (m, 2H), 3.75 (s, 6H), 3.65 (s, 3H), 3.55 (m, 1H), 3.4 (m, 1H), 2.45 (m, 2H), 1.6 (d, 3H) ppm。
配製物實施例
可濕性粉劑 | a) | b) | c) |
活性成分 | 25% | 50% | 75% |
木質素磺酸鈉 | 5% | 5% | - |
月桂基硫酸鈉 | 3% | - | 5% |
二異丁基萘磺酸鈉 | - | 6% | 10% |
苯酚聚乙二醇醚 | - | 2% | - |
(7-8 mol的環氧乙烷) | |||
高度分散的矽酸 | 5% | 10% | 10% |
高嶺土 | 62% | 27% | - |
將該組合與該等佐劑充分混合並且將混合物在適當的研磨機中充分研磨,從而獲得了可以用水稀釋而給出所希望的濃度的懸浮液的可濕性粉劑。
可乳化濃縮物 | |
活性成分 | 10% |
辛基酚聚乙二醇醚 | 3% |
(4-5 mol的環氧乙烷) | |
十二烷基苯磺酸鈣 | 3% |
蓖麻油聚乙二醇醚(35 mol環氧乙烷) | 4% |
環己酮 | 30% |
二甲苯混合物 | 50% |
在植物保護中可以使用的具有任何所要求的稀釋的乳液可以藉由用水稀釋由這種濃縮物中獲得。
粉塵劑 | a) | b) | c) |
活性成分 | 5% | 6% | 4% |
滑石 | 95% | - | - |
高嶺土 | - | 94% | - |
礦物填料 | - | - | 96% |
藉由將該組合與載劑混合並且將混合物在適當的研磨機中研磨而獲得即用型粉塵劑。
擠出機顆粒劑 | |
活性成分 | 15% |
木質素磺酸鈉 | 2% |
羧甲基纖維素 | 1% |
高嶺土 | 82% |
將該組合與該等佐劑混合並且研磨,並且將混合物用水濕潤。將混合物擠出並且然後在空氣流中乾燥。
包衣顆粒劑 | |
活性成分 | 8% |
聚乙二醇(分子量200) | 3% |
高嶺土 | 89% |
將這種精細研磨的組合在混合器中均勻地施用於用聚乙二醇濕潤的高嶺土中。以此方式獲得無塵的包衣顆粒劑。
懸浮液濃縮物
活性成分 | 40% |
丙二醇 | 10% |
壬基酚聚乙二醇醚(15 mol的環氧乙烷) | 6% |
木質素磺酸鈉 | 10% |
羧甲基纖維素 | 1% |
矽油(處於在水中75%的乳液的形式) | 1% |
水 | 32% |
將精細地研磨的組合與佐劑緊密地混合,得到懸浮液濃縮物,從該懸浮液濃縮物可以藉由用水稀釋獲得具有任何所希望的稀釋度的懸浮液。
緩釋的膠囊懸浮液
將28份的組合與2份的芳香族溶劑以及7份的甲苯二異氰酸酯/聚甲烯(polymethylene)-聚苯基異氰酸酯-混合物(8 : 1)進行混合。將此混合物在1.2份的聚乙烯醇、0.05份的消泡劑以及51.6份的水的混合物中進行乳化直至達到所希望的粒度。向此乳液中添加在5.3份的水中的2.8份的1,6-己二胺混合物。將混合物攪拌直至聚合反應完成。
將獲得的膠囊懸浮液藉由添加0.25份的增稠劑以及3份的分散劑進行穩定。該膠囊懸浮液配製物包含28%的活性成分。該介質膠囊的直徑係8-15微米。
將所得配製物作為在適合於此目的的裝置中的水性懸浮液施用至種子上。
生物學實施例 出苗前生物學功效
將雜草和/或作物的種子播種在盆中的標準土壤中(長芒莧(
Amaranthus palmeri,AMAPA)、多年生黑麥草(
Lolium perenne,LOLPE)、白苞猩猩草(
Euphorbia heterophylla,EPHHL)、牽牛花(
Ipomoea hederacea,IPOHE)、大狗尾草(
Setaria faberi,SETFA)、稗草(
Echinochloa crus-galli,ECHCG))。在溫室中的受控條件(在24°C/19°C下,白天/夜晚;16小時光照)下培養一天之後,用如下得到的水性噴霧溶液噴灑植物:將工業活性成分在少量丙酮和稱為IF50(11.12% Emulsogen EL360 TM + 44.44% N-甲基吡咯啶酮 + 44.44% Dowanol DPM乙二醇醚)的特殊溶劑和乳化劑混合物中配製,以產生50 g/l溶液,然後使用0.2% Genapol XO80作為稀釋劑將其稀釋以得到所需最終劑量的測試化合物。
該等測試植物然後在溫室中的受控條件(在24°C/18°C下,白天/夜晚;15小時光照;50%濕度)下生長,並且每日澆水兩次。13天後,評估測試(100 = 對植物的完全損害;0 = 無植物損害)。結果在下表2中示出。
[ 表 2 ]
出苗後生物學功效
化合物 | 比率 ( g/ha ) | 物種 | |||||
AMAPA | LOLPE | EPHHL | IPOHE | SETFA | ECHCG | ||
9-245 | 250 | 100 | 80 | 100 | 90 | 100 | 80 |
9-272 | 250 | 100 | 90 | 100 | 100 | 100 | 80 |
雜草和/或作物的種子播種在盆中的標準土壤中(長芒莧(AMAPA)、藜草(
Chenopodium album,CHEAL)、白苞猩猩草(EPHHL)、牽牛花(IPOHE)、牛筋草(
Eleusine indica,ELEIN)、多年生黑麥草(LOLPE)、馬唐(
Digitaria sanguinalis,DIGSA)、大狗尾草(SETFA)、稗草(ECHCG))。在溫室中的受控條件(在24°C/19°C下,白天/夜晚;16小時光照)下培養14天之後,用如下得到的水性噴霧溶液噴灑植物:將技術活性成分在少量丙酮和稱為IF50(11.12% Emulsogen EL360 TM + 44.44% N-甲基吡咯啶酮 + 44.44% Dowanol DPM乙二醇醚)的特殊溶劑和乳化劑混合物中配製,以產生50 g/l溶液,然後使用0.2% Genapol XO80作為稀釋劑將其稀釋以得到所需最終劑量的測試化合物。
該等測試植物然後在溫室中的受控條件(在24°C/18°C下,白天/夜晚;15小時光照;50%濕度)下生長,並且每日澆水兩次。13天後,評估測試(100 = 對植物的完全損害;0 = 無植物損害)。結果在下表3中示出。
[ 表 3 ]
化合物 | 比率 ( g/ha ) | 物種 | ||||||||
AMAPA | CHEAL | EPHHL | IPOHE | ELEIN | LOLPE | DIGSA | SETFA | ECHCG | ||
9-245 | 250 | 100 | 100 | 90 | 100 | 80 | 100 | 30 | 40 | 70 |
9-272 | 250 | 80 | 90 | 90 | 100 | 80 | 100 | 70 | 90 | 40 |
無
無
無
Claims (15)
- 一種具有式 (I) 的化合物或其農藝學上可接受的鹽, (I) 其中 X 1、X 2和X 3各自獨立地選自氧和硫; Y係C-H或氮; B係O、S、或NR 5; D係(CR 6R 7) n; m係從0至2的整數; n係從1至4的整數; R 1係氫或C 1-C 6烷基; R 2係氫、胺基、C 1-C 6烷基、C 3-C 6烯基或C 3-C 6炔基; R 3係氫、鹵素、C 1-C 4烷基、C 1-C 4鹵代烷基、C 1-C 4烷氧基、C 1-C 4鹵代烷氧基、C 1-C 4烷硫基或C 1-C 4烷基磺醯基; R 4係氫、鹵素、氰基、硝基、胺基羰基、胺基硫代羰基、C 1-C 4烷基、C 1-C 4鹵代烷基、C 1-C 4烷氧基、C 1-C 4鹵代烷氧基或C 1-C 4烷基磺醯基; R 5係氫、羥基、C 1-C 6烷基或C 1-C 4烷氧基; R 6和R 7各自獨立地選自氫、鹵素、C 1-C 6烷基、C 1-C 6鹵代烷基、羥基、C 1-C 4烷氧基、C 1-C 4烷氧基羰基或CH 2OR 12;前提係R 6和R 7在同一碳原子上不皆為羥基; 或者,在同一碳原子或不同碳原子上的兩個基團R 6和R 7一起形成C 1-C 5伸烷基鏈,該鏈含有0、1或2個氧原子,被1-3個基團R 15取代; 或者,在同一碳原子上的兩個基團R 6和R 7與它們所附接的碳一起形成C 2烯烴; R 8係OR 9、SR 9或NR 10R 11; R 9係氫、C 1-C 10烷基、C 1-C 10鹵代烷基、C 3-C 6烯基、C 3-C 6鹵代烯基、C 3-C 6炔基、C 1-C 4烷氧基C 1-C 6烷基、C 1-C 4鹵代烷氧基C 1-C 6烷基、C 6-C 10芳基C 1-C 3烷基、被1-4個基團R 13取代的C 6-C 10芳基C 1-C 3烷基、雜芳基C 1-C 3烷基或被1-3個基團R 13取代的雜芳基C 1-C 3烷基; R 10係氫、C 1-C 6烷基或SO 2R 14; R 11係氫或C 1-C 6烷基;或者 R 10和R 11與它們所附接的氮一起形成3員至6員雜環基環,該雜環基環視需要含有氧原子; R 12係氫、C 1-C 4烷基或C 1-C 4烷基羰基; R 13各自獨立地選自鹵素、C 1-C 4烷基、C 1-C 4鹵代烷基、C 1-C 4烷氧基、C 1-C 4鹵代烷氧基、氰基和C 1-C 4烷基磺醯基; R 14係C 1-C 4烷基、C 1-C 4鹵代烷基或C 1-C 4烷基(C 1-C 4烷基)胺基; R 15各自獨立地選自氫、鹵素、C 1-C 4烷基和C 1-C 4鹵代烷基; R 16和R 17獨立地選自氫、鹵素、C 1-C 6烷基、C 1-C 6鹵代烷基、C 1-C 4烷氧基和CH 2OR 12; 或者,兩個基團R 16和R 17一起形成C 2-C 5伸烷基鏈,該伸烷基鏈含有0、1或2個氧原子,被1-3個基團R 15取代; 或者,兩個基團R 16和R 17與它們所附接的碳一起形成C 2烯烴; 或其鹽或N-氧化物。
- 如請求項1所述之化合物,其中,X 1係硫。
- 如請求項1或請求項2所述之化合物,其中,X 2係氧。
- 如請求項1或請求項2所述之化合物,其中,X 3係氧。
- 如請求項1或請求項2所述之化合物,其中,Y係C-H。
- 如請求項1或請求項2所述之化合物,其中,B係O、NH或NMe。
- 如請求項1或請求項2所述之化合物,其中,n係從1至2的整數。
- 如請求項7所述之化合物,其中,n係2。
- 如請求項1或請求項2所述之化合物,其中,R 1係氫或C 1-C 4烷基。
- 如請求項1或請求項2所述之化合物,其中,R 2係氫、C 1-C 4烷基或C 3-C 4炔基。
- 如請求項1或請求項2所述之化合物,其中,R 3係氫、氯或氟。
- 如請求項1或請求項2所述之化合物,其中,R 4係氫、氯、溴、氰基或胺基硫代羰基。
- 如請求項1或請求項2所述之化合物,其中,R 6和R 7各自獨立地選自氫、鹵素、C 1-C 4烷基和C 1-C 4烷氧基羰基。
- 一種農用化學組成物,其包含除草有效量的如請求項1至13中任一項所定義的具有式 (I) 的化合物、以及農用化學上可接受的稀釋劑或載劑。
- 一種控制或預防不希望的植物生長之方法,其中將除草有效量的如請求項1至13中任一項所定義的具有式 (I) 的化合物、或如請求項14所述之組成物施用至該植物、其部分或其場所。
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