CN1192737A - 苄基羟基胺及制备其的中间产物 - Google Patents
苄基羟基胺及制备其的中间产物 Download PDFInfo
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- CN1192737A CN1192737A CN96196204A CN96196204A CN1192737A CN 1192737 A CN1192737 A CN 1192737A CN 96196204 A CN96196204 A CN 96196204A CN 96196204 A CN96196204 A CN 96196204A CN 1192737 A CN1192737 A CN 1192737A
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- China
- Prior art keywords
- group
- alkyl
- alkoxy
- formula
- carbonyl
- Prior art date
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- LVCDXCQFSONNDO-UHFFFAOYSA-N n-benzylhydroxylamine Chemical class ONCC1=CC=CC=C1 LVCDXCQFSONNDO-UHFFFAOYSA-N 0.000 title claims abstract description 35
- 239000000543 intermediate Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 114
- 239000001257 hydrogen Substances 0.000 claims abstract description 71
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 71
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 48
- 150000002367 halogens Chemical class 0.000 claims abstract description 48
- 125000001424 substituent group Chemical group 0.000 claims abstract description 45
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 32
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 28
- 150000003839 salts Chemical class 0.000 claims abstract description 24
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 20
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 14
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims abstract description 14
- 239000004009 herbicide Substances 0.000 claims abstract description 11
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 11
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims abstract description 10
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- 230000035613 defoliation Effects 0.000 claims abstract description 7
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 3
- -1 C1-C6-Alkylsulfinyl radical Chemical class 0.000 claims description 319
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 112
- 238000000034 method Methods 0.000 claims description 72
- 239000000203 mixture Substances 0.000 claims description 48
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 47
- 150000003254 radicals Chemical class 0.000 claims description 47
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 40
- 230000008569 process Effects 0.000 claims description 35
- 150000002431 hydrogen Chemical class 0.000 claims description 34
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 32
- 239000000460 chlorine Substances 0.000 claims description 32
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 20
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 20
- 239000001301 oxygen Substances 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 238000001035 drying Methods 0.000 claims description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 230000002363 herbicidal effect Effects 0.000 claims description 16
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 239000011593 sulfur Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- 125000004434 sulfur atom Chemical group 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- 150000001448 anilines Chemical class 0.000 claims description 6
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- 230000012010 growth Effects 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 claims description 3
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 150000002828 nitro derivatives Chemical class 0.000 claims description 3
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical class NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 239000000126 substance Substances 0.000 claims 5
- 239000004094 surface-active agent Substances 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 230000008635 plant growth Effects 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 1
- 125000006193 alkinyl group Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
- 238000006243 chemical reaction Methods 0.000 description 46
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- 239000002585 base Substances 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- 241000196324 Embryophyta Species 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 239000013543 active substance Substances 0.000 description 24
- 239000002904 solvent Substances 0.000 description 23
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
- 238000009835 boiling Methods 0.000 description 20
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 19
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- 229910052783 alkali metal Inorganic materials 0.000 description 18
- 239000002253 acid Substances 0.000 description 17
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 15
- 239000003921 oil Substances 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- 125000001931 aliphatic group Chemical group 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 239000007858 starting material Substances 0.000 description 14
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 13
- 150000004292 cyclic ethers Chemical class 0.000 description 13
- 239000003085 diluting agent Substances 0.000 description 13
- 239000003960 organic solvent Substances 0.000 description 13
- 239000008096 xylene Substances 0.000 description 13
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 235000019198 oils Nutrition 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 229910000104 sodium hydride Inorganic materials 0.000 description 12
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 10
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 10
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- 239000012312 sodium hydride Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 9
- 229940093499 ethyl acetate Drugs 0.000 description 9
- 235000019439 ethyl acetate Nutrition 0.000 description 9
- 150000007530 organic bases Chemical class 0.000 description 9
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 7
- 230000002378 acidificating effect Effects 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 7
- 150000001340 alkali metals Chemical class 0.000 description 7
- 125000003277 amino group Chemical group 0.000 description 7
- 150000001491 aromatic compounds Chemical class 0.000 description 7
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 7
- 239000012442 inert solvent Substances 0.000 description 7
- 239000002798 polar solvent Substances 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 7
- 241000219146 Gossypium Species 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 6
- 150000008041 alkali metal carbonates Chemical class 0.000 description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
- 239000004359 castor oil Substances 0.000 description 6
- 235000019438 castor oil Nutrition 0.000 description 6
- 229960004132 diethyl ether Drugs 0.000 description 6
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 229940052303 ethers for general anesthesia Drugs 0.000 description 6
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 235000011181 potassium carbonates Nutrition 0.000 description 6
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 5
- 150000008046 alkali metal hydrides Chemical class 0.000 description 5
- 125000000304 alkynyl group Chemical group 0.000 description 5
- 239000000010 aprotic solvent Substances 0.000 description 5
- 235000013877 carbamide Nutrition 0.000 description 5
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 5
- 239000003638 chemical reducing agent Substances 0.000 description 5
- 150000008282 halocarbons Chemical class 0.000 description 5
- 239000003701 inert diluent Substances 0.000 description 5
- 150000007529 inorganic bases Chemical class 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 5
- 229910000105 potassium hydride Inorganic materials 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- 241000335053 Beta vulgaris Species 0.000 description 4
- 240000002791 Brassica napus Species 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- 241000371652 Curvularia clavata Species 0.000 description 4
- 235000010469 Glycine max Nutrition 0.000 description 4
- 244000068988 Glycine max Species 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 235000002595 Solanum tuberosum Nutrition 0.000 description 4
- 244000061456 Solanum tuberosum Species 0.000 description 4
- 241000209140 Triticum Species 0.000 description 4
- 235000021307 Triticum Nutrition 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 230000001276 controlling effect Effects 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910052987 metal hydride Inorganic materials 0.000 description 4
- 150000004681 metal hydrides Chemical class 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- 239000006072 paste Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 125000005537 sulfoxonium group Chemical group 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- 235000006463 Brassica alba Nutrition 0.000 description 3
- 244000140786 Brassica hirta Species 0.000 description 3
- 235000011293 Brassica napus Nutrition 0.000 description 3
- 240000007154 Coffea arabica Species 0.000 description 3
- 235000004341 Gossypium herbaceum Nutrition 0.000 description 3
- 240000002024 Gossypium herbaceum Species 0.000 description 3
- 235000003222 Helianthus annuus Nutrition 0.000 description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 244000061457 Solanum nigrum Species 0.000 description 3
- 240000005592 Veronica officinalis Species 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 229910001413 alkali metal ion Inorganic materials 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 125000005237 alkyleneamino group Chemical group 0.000 description 3
- 238000005576 amination reaction Methods 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- NNTOJPXOCKCMKR-UHFFFAOYSA-N boron;pyridine Chemical class [B].C1=CC=NC=C1 NNTOJPXOCKCMKR-UHFFFAOYSA-N 0.000 description 3
- 150000001733 carboxylic acid esters Chemical class 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
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- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
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- 125000005843 halogen group Chemical group 0.000 description 1
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- 125000006343 heptafluoro propyl group Chemical group 0.000 description 1
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- YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical compound OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
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- 238000005984 hydrogenation reaction Methods 0.000 description 1
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- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
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- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 159000000014 iron salts Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
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- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 1
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- 239000004571 lime Substances 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
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- 239000000395 magnesium oxide Substances 0.000 description 1
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- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 125000002960 margaryl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
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- 229940102396 methyl bromide Drugs 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- OIRDBPQYVWXNSJ-UHFFFAOYSA-N methyl trifluoromethansulfonate Chemical compound COS(=O)(=O)C(F)(F)F OIRDBPQYVWXNSJ-UHFFFAOYSA-N 0.000 description 1
- OKHRRIGNGQFVEE-UHFFFAOYSA-N methyl(diphenyl)silicon Chemical compound C=1C=CC=CC=1[Si](C)C1=CC=CC=C1 OKHRRIGNGQFVEE-UHFFFAOYSA-N 0.000 description 1
- 239000012022 methylating agents Substances 0.000 description 1
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- 230000011987 methylation Effects 0.000 description 1
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- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
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- 125000001477 organic nitrogen group Chemical group 0.000 description 1
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- 150000002924 oxiranes Chemical class 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 125000000913 palmityl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
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- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
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- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
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- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 230000001737 promoting effect Effects 0.000 description 1
- 125000006238 prop-1-en-1-yl group Chemical group [H]\C(*)=C(/[H])C([H])([H])[H] 0.000 description 1
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- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical class C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
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- 230000001105 regulatory effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
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- 239000000600 sorbitol Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- OKQKDCXVLPGWPO-UHFFFAOYSA-N sulfanylidenephosphane Chemical compound S=P OKQKDCXVLPGWPO-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
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- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000005987 sulfurization reaction Methods 0.000 description 1
- NBNBICNWNFQDDD-UHFFFAOYSA-N sulfuryl dibromide Chemical compound BrS(Br)(=O)=O NBNBICNWNFQDDD-UHFFFAOYSA-N 0.000 description 1
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- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 125000005304 thiadiazolidinyl group Chemical group 0.000 description 1
- 125000005305 thiadiazolinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 150000007970 thio esters Chemical group 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002827 triflate group Chemical class FC(S(=O)(=O)O*)(F)F 0.000 description 1
- 150000008648 triflates Chemical class 0.000 description 1
- 235000018322 upland cotton Nutrition 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical compound C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
-
- 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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C239/00—Compounds containing nitrogen-to-halogen bonds; Hydroxylamino compounds or ethers or esters thereof
- C07C239/08—Hydroxylamino compounds or their ethers or esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C239/00—Compounds containing nitrogen-to-halogen bonds; Hydroxylamino compounds or ethers or esters thereof
- C07C239/08—Hydroxylamino compounds or their ethers or esters
- C07C239/10—Hydroxylamino compounds or their ethers or esters having nitrogen atoms of hydroxylamino groups further bound to carbon atoms of unsubstituted hydrocarbon radicals or of hydrocarbon radicals substituted by halogen atoms or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C239/00—Compounds containing nitrogen-to-halogen bonds; Hydroxylamino compounds or ethers or esters thereof
- C07C239/08—Hydroxylamino compounds or their ethers or esters
- C07C239/20—Hydroxylamino compounds or their ethers or esters having oxygen atoms of hydroxylamino groups etherified
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Abstract
苄基羟基胺Ⅰ其中X=-N(R7)-O-;Y=O,S;R1=卤素、CN、NO2、CF3;R2=氢、卤素;R3=氢、NH2、CH3;R4=氢、卤素、C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷硫基、C1-C6-烷基亚硫酰基或C1-C6-烷基磺酰基;R5=氢、卤素、C1-C6-烷基;R6=氢、C1-C6-烷基、C1-C6-卤代烷基、C3-C6-环烷基、C2-C6-链烯基;R8=氢、C1-C6-烷基、C3-C8-环烷基、C1-C6-卤代烷基、C3-C6-链烯基或C3-C6-炔基,最后提及的5个基团中的每个基团可有1—3个取代基与其结合,和其中R3、R7和/或R8=氢的化合物Ⅰ的盐,用作除草剂,并用于植物的干燥/脱叶。
Description
本发明涉及新的通式I的苄基羟基胺:式中变量具有下面的含义:
X是-N(R7)-O-,它可通过氧或氮与R8键合;
Y是氧或硫;
R1是卤素、氰基、硝基或三氟代甲基;
R2是氢或卤素;
R3是氢、氨基或甲基;
R4是氢、卤素、C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷硫基、C1-C6-烷基亚硫酰基或C1-C6-烷基磺酰基;
R5是氢、卤素或C1-C6-烷基;
R6是氢、C1-C6-烷基、C1-C6-卤代烷基、C3-C6-环烷基或C2-C6-链烯基;
R7是氢、C1-C6-烷基、C3-C8-环烷基、C1-C6-卤代烷基、C3-C6-链烯基、C3-C6-炔基、(C1-C6-烷基)羰基、(C3-C6-链烯基)羰基、(C3-C6-炔基)羰基、(C1-C6-烷氧基)羰基、(C2-C6-链烯基氧基)羰基、(C2-C6-炔基氧基)羰基、(C1-C6-烷硫基)羰基、C1-C6-烷基磺酰基、C1-C6-烷基氨基甲酰基,最后提及的14个基团中每个基团可任选地有1-3个取代基与其结合,这些取代基各选自于由下列基团组成的组中:
-硝基、氰基、卤素、C3-C8-环烷基、羟基、C1-C6-烷氧基、C3-C8-环烷氧基、C3-C6-链烯基氧基、C3-C6-炔基氧基、C1-C6-烷氧基-C1-C6-烷氧基、C1-C6-烷硫基、(C1-C6-烷基)羰基、(C1-C6-烷基)羰基氧基、C1-C6-烷基亚硫酰基、C1-C6-烷基磺酰基、C1-C6-亚烷基氨氧基、C1-C6-烷基氨基甲酰基,
-苯基、苯氧基或苯磺酰基,其中这些苯环可以是未被取代的或带有1-3个取代基,这些取代基在每种情况下都选自于由卤素、硝基、氰基、C1-C6-烷基、C1-C6-烷氧基和C1-C6-卤代烷基组成的组中。
-一个具有1-3个杂原子的3-7元杂环基或杂环氧基团,这些杂原子选自于由2个氧原子、2个硫原子和3个氮原子组成的组中,该杂环可以是饱和、部分或完全未饱和或是芳族的,并且如果需要的话,有1-3个取代基与其结合,这些取代基在每种情况下都选自于由卤素、硝基、氰基、C1-C6-烷基、C1-C6-烷氧基、C1-C6-卤代烷基和(C1-C6-烷基)羰基组成的组中,
-一个-CO-Z1R9、-OCO-Z1R9、或者-N(R9)R10基团,或者
R7是C3-C8-环烷基羰基、苯基羰基、苯磺酰基或苯基氨基甲酰基,这4个基团可以未被取代,或有1-3个取代基与其结合,在每种情况下这些取代基选自于由卤素、硝基、氰基、C1-C6-烷基、C1-C6-烷氧基和C1-C6-卤代烷基组成的组中;
R8是氢、C1-C6-烷基、C3-C8-环烷基、C1-C6-卤代烷基、C3-C6-链烯基或C3-C6-炔基,任选地,最后提及的5个基团中的每个基团可以有1-3个取代基与其结合,在每种情况下这些取代基都选自于由以下基团组成的组中:
-硝基、氰基、卤素、C3-C8-环烷基、羟基、C1-C6-烷氧基、C3-C8-环烷氧基、C3-C6-链烯基氧基、C3-C6-炔基氧基、C1-C6-烷氧基-C1-C6-烷氧基、C1-C6-烷硫基、C1-C6-烷基亚硫酰基、C1-C6-烷基磺酰基、C1-C6-亚烷基氨氧基,
-苯基、苯氧基或苯磺酰基,其中这些苯环可以未被取代或有1-3个取代基与其结合,在每种情况下这些取代基都选自于由硝基、氰基、卤素、C1-C6-烷基、C1-C6-烷氧基和C1-C6-卤代烷基组成的组中,
-一个具有1-3个杂原子的3-7元杂环基团或杂环氧基团,这些杂原子选自于由2个氧原子、2个硫原子和3个氮原子组成的组中,该杂环可以是饱和、部分或完全未饱和或是芳族的,并且如果需要的话,有1-3个取代基与其结合,在每种情况下这些取代基都选自于由卤素、硝基、氰基、C1-C6-烷基、C1-C6-烷氧基、C1-C6-卤代烷基和(C1-C6-烷基)羰基组成的组中,
-一个-CO-Z2R11、-OCO-Z2R11、或者-N(R11)R12基团,
Z1是一个化学键、氧、硫或-N(R10)-;
Z2是一个化学键、氧、硫或-N(R12)-;
R9、R11相互独立地是氢、C1-C6-烷基、C1-C6-卤代烷基、C3-C8-环烷基、C3-C6-链烯基、C3-C6-炔基、C1-C6-烷氧基-C1-C6-烷基、(C1-C6-烷氧基)羰基-C1-C6-烷基、苯基或苯基-C1-C6-烷基,苯基和苯基烷基的苯环可以未被取代或有1-3个取代基与其结合,在每种情况下这些取代基都选自于由硝基、氰基、卤素、C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷氧基或(C1-C6-烷基)羰基组成的组中,或者
Z1和R9和/或Z2和R11在每种情况下共同为一个通过氮结合的3-7元杂环,并且该杂环具有1-3个杂原子,这些杂原子选自于由2个氧原子、2个硫原子和3个氮原子组成的组中,该杂环可以是饱和、部分或完全未饱和或是芳族的,并且如果需要的话,有1-3个取代基与其结合,在每种情况下这些取代基都选自于由硝基、氰基、卤素、C1-C6-烷基、C1-C6-卤代烷基和C1-C6-烷氧基组成的组中;
R10、R12相互独立地是氢、羟基、C1-C6-烷基、C3-C8-环烷基、或C1-C6-烷氧基,
以及其中R3、R7和/或R8是氢的那些化合物I在农业上有用的盐。
而且,本发明还涉及到
-化合物I作为除草剂或在植物干燥和/或脱叶方面的应用,
-除草组合物和植物干燥和/或脱叶的组合物,这些组合物含有作为活性组分的化合物I,
-使用化合物I控制不希望的植物生长和对植物干燥和/脱叶的方法,
-使用化合物I制备除草组合物和植物干燥和/或脱叶的组合物的方法,以及
-化学式IV、V、XIII、XVI、XVII、XIX和XXIII的新的中间产物,化合物I能够由它们制得。
WO 93/06090和EP-A 408 382已描述了某些作为除草剂和用于植物干燥和/或脱叶的3-苯基尿嘧啶,它们因适当选择一些取代基而不同于本发明的化合物I,主要不同之处在于苯环有一个亚氨基甲基而不是取代基-CH(R6)-X-R8与其结合。
Rb特别是肟基甲基或氧基亚氨基甲基。
最后,DE-A 42 37 920公开了某些3-芳基尿嘧啶,特别是具有下述化学式III的化合物式中
Rc是氢、C1-C4-烷基、C1-C4-卤代烷基、C3/C4-链烯基或C3/C4-炔基;
Rd和Re是氢、C1-C8-烷基、C3-C7-环烷基或C3-C7-环烷基-C1-C4-烷基;
Rf是氢、C1-C5-烷基、C1-C4-烷氧基-C1-C4-烷基、C3-C8-环烷基、C3-C8-环烷基-C1-C4-烷基、C1-C5-卤代烷基、C2-C5-链烯基、C2-C5-炔基、未取代或取代的芳基或苄基,或是一个酮、酯或硫代酯基团,以及
R5是氢、卤素或C1-C4-烷基都适用于控制杂草。
但是,已知化合物的除草特性并不总是完全令人满意的。因此,本发明的一个目的是提供新的特别具有除草活性的化合物,用该化合物比到目前为止可能采用的化合物更能够使不希望的植物得到更好的目标控制。
另一个目的是提供新的具有干燥/脱叶作用的化合物。
因此,我们已看到这一目的可以通过化学式I的苄基羟基胺及其除草作用实现。
而且,已发现含有化合物I的除草组合物,并且该组合物具有非常好的除草作用。并且,已经发现制备这些组合物的方法和使用化合物I控制不希望的植物生长的方法。
而且,已经发现化合物I还适用于植物部分脱叶和干燥,合适的植物是作物植物如棉花、马铃薯、油菜、向日葵、大豆或蚕豆,特别是棉花。在这方面,已发现用于植物干燥和/或脱叶的组合物、制备这些组合物的方法,以及用化合物I为植物干燥和/或脱叶的方法。
取决于其取代类型,化学式I的化合物可以得到一个或更多的手性中心,在这一情况下它们以对映体或非对映体混合物的形式存在。本发明涉及纯的对映体或非对映体,还涉及它们的混合物。
如果R3、R7和/或R8是氢,苄基羟基胺I能够以其在农业上可用的盐的形式存在,该盐的种类通常并不关键。通常,合适的盐是与游离化合物I相比不会不利于影响除草作用的那些碱的盐。
特别合适的碱式盐是碱金属盐,优选的是钠盐和钾盐,碱土金属盐,优选的是钙盐和镁盐,过渡金属盐,优选的是锌盐和铁盐,以及铵盐,如果需要的话,其铵离子可带有1-4个C1-C4-烷基或羟基-C1-C4-烷基取代基和/或一个苯基或苄基取代基,优选的是二异丙基铵盐、四甲基铵盐、四丁基铵盐、三甲基苄基铵-和三甲基(2-羟乙基)铵盐,还有鏻盐、锍盐,如优选地是三(C1-C4-烷基)锍盐和氧化锍盐,如优选地是三(C1-C4-烷基)氧化锍盐。
上面提到的取代基R4-R12的有机部分或作为苯环或杂环上残基的有机部分是该组的各个成员的单个列举的集合术语。所有的碳链,即所有的烷基、卤代烷基、烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、烷基羰基、烷氧基羰基、链烯基、链烯基氧基、链烯基羰基、炔基、炔基氧基、炔基羰基和亚烷基氨基氧基部分可以是直链或支链的。除非另外指出,卤化的取代基优选地有1-5个相同的或不同的卤素原子与它们结合。在每种情况下卤素是氟、氯、溴或碘。
其它意义的例子是
-C1-C4-烷基和(C1-C6-烷基)羰基、(C1-C6-烷基)羰基氧基、C1-C6-烷基氨基甲酰基、C1-C6-烷氧基-C1-C6-烷基和(C1-C6-烷氧基)羰基-C1-C6-烷基的烷基部分:甲基、乙基、n-丙基、1-甲基乙基、n-丁基、1-甲基-丙基、2-甲基丙基、1,1-二甲基乙基、n-戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、2,2-二甲基-丙基、1-乙基丙基、1,1-二甲基丙基、1,2-二甲基-丙基、n-己基、1-甲基戊基、2-甲基戊基、3-甲基戊基、4-甲基戊基、1,1-二甲基丁基、1,2-二甲基丁基、1,3-二甲基丁基、2,2-二甲基丁基、2,3-二甲基丁基、3,3-二甲基丁基、1-乙基丁基、2-乙基丁基、1,1,2-三甲基丙基、1,2,2-三甲基丙基、1-乙基-1-甲基丙基或1-乙基-2-甲基丙基;
-C1-C6-卤代烷基:一个如上面提到的C1-C6-烷基,它部分或全部被氟、氯、溴和/或碘取代,如氯甲基、二氯甲基、、三氯甲基、氟甲基、二氟甲基、三氟甲基、一氯一氟甲基、二氯一氟甲基、一氯二氟甲基、2-氟乙基、2-氯乙基、2-溴乙基、2-碘乙基、2,2-二氟乙基、2,2,2-三氟乙基、2-氯-2-氟乙基、2-氯-2,2-二氟乙基、2,2二氯-2-氟乙基、2,2,2-三氯乙基、五氟乙基、2-氟丙基、3-氟丙基、2,2-二氟丙基、2,3-二氟丙基、2-氯丙基、3-氯丙基、2,3-二氯丙基、2-溴丙基、3-溴丙基、3,3,3-三氟丙基、3,3,3-三氯丙基、2,2,3,3,3-五氟丙基、七氟丙基、1-(氟代甲基)-2-氟乙基、1-(氯代甲基)-2-氯乙基、1-(溴代甲基)-2-溴乙基、4-氟丁基、4-氯丁基、4-溴丁基、九氟丁基、5-氟戊基、5-氯戊基、5-溴戊基、5-碘戊基、十一氟代戊基、6-氟己基、6-氯己基、6-溴己基、6-碘己基或十二氟代己基;
-苯基-C1-C6-烷基:如苄基、1-苯乙基、2-苯乙基、1-苯基丙-1-基、2-苯基丙-1-基、3-苯基丙-1-基、1-苯基丁-1-基、2-苯基丁-1-基、3-苯基丁-1-基、4-苯基丁-1-基、1-苯基丁-2-基、2-苯基丁-2-基、3-苯基丁-2-基、3-苯基丁-2-基、4-苯基丁-2-基、1-(苯甲基)乙-1-基、1-(苯甲基)-1-(甲基)-乙-1-基或1-(苯甲基)丙-1-基,优选的是苄基、2-苯乙基或2-苯基-己-6-基;
-C3-C6-链烯基和C3-C6-链烯基氧基和(C3-C6-链烯基)羰基的链烯基部分:丙-1-烯-1-基、丙-2-烯-1-基、1-甲基乙烯基、n-丁烯-1-基、n-丁烯-2-基、n-丁烯-3-基、1-甲基丙-1-烯-1-基、2-甲基丙-1-烯-1-基、1-甲基丙-2-烯-1-基或2-甲基丙-2-烯-1-基、n-戊烯-1-基、n-戊烯-2-基、n-戊烯-3-基、n-戊烯-4-基、1-甲基丁-1-烯-1-基、2-甲基-丁-1-烯-1-基、3-甲基丁-1-烯-1-基、1-甲基丁-2-烯-1-基、2-甲基丁-2-烯-1-基、3-甲基丁-2-烯-1-基、1-甲基丁-3-烯-1-基、2-甲基丁-3-烯-1-基、3-甲基丁-3-烯-1-基、1,1-二甲基丙-2-烯-1-基、1,2-二甲基丙-1-烯-1-基、1,2-二甲基丙-2-烯-1-基、1-乙基丙-1-烯-2-基、1-乙基丙-2-烯-1-基、n-己-1-烯-1-基、n-己-2-烯-1-基、n-己-3-烯-1-基、n-己-4-烯-1-基、n-己-5-烯-1-基、1-甲基戊-1-烯-1-基、2-甲基戊-1-烯-1-基、3-甲基戊-1-烯-1-基、4-甲基戊-1-烯-1-基、1-甲基戊-2-烯-1-基、2-甲基戊-2-烯-1-基、3-甲基戊-2-烯-1-基、4-甲基戊-2-烯-1-基、1-甲基戊-3-烯-1-基、2-甲基戊-3-烯-1-基、3-甲基戊-3-烯-1-基、4-甲基戊-3-烯-1-基、1-甲基戊-4-烯-1-基、2-甲基戊-4-烯-1-基、3-甲基戊-4-烯-1-基、4-甲基戊4-烯-1-基、1,1-二甲基丁-2-烯-1-基、1,1-二甲基丁-3-烯-1-基、1,2-二甲基丁-1-烯-1-基、1,2-二甲基丁-2-烯-1-基、1,2-二甲基丁-3-烯-1-基、1,3-二甲基丁-1-烯-1-基、1,3-二甲基丁-2-烯-1-基、1,3-二甲基丁-3-烯-1-基、2,2-二甲基丁-3-烯-1-基、2,3-二甲基丁-1-烯-1-基、2,3-二甲基丁-2-烯-1-基、2,3-二甲基丁-3-烯-1-基、3,3-二甲基丁-1-烯-1-基、3,3-二甲基丁-2-烯-1-基、1-乙基丁-1-烯-1-基、1-乙基丁-2-烯-1-基、1-乙基丁-3-烯-1-基、2-乙基丁-1-烯-1-基、2-乙基丁-2-烯-1-基、2-乙基丁-3-烯-1-基、1,1,2-三甲基丙-2-烯-1-基、1-乙基-1-甲基丙-2-烯-1-基、1-乙基-2-甲基丙-1-烯-1-基或1-乙基-2-甲基丙-2-烯-1-基;
-C3-C6-炔基和C3-C6-炔基氧基和(C3-C6-炔基)羰基的炔基部分:丙-1-炔-1-基、丙-2-炔-1-基、丁-1-炔-1-基、丁-1-炔-3-基、丁-1-炔-4-基、丁-2-炔-1-基、戊-1-炔-1-基、n-戊-1-炔-3-基、n-戊-1-炔-4-基、n-戊-1-炔-5-基、n-戊-2-炔-1-基、n-戊-2-炔-4-基、n-戊-2-炔-5-基、3-甲基丁-1-炔-3-基、3-甲基丁-1-炔-4-基、n-己-1-炔-1-基、n-己-1-炔-3-基、n-己-1-炔-4-基、n-己-1-炔-5-基、n-己-1-炔-6-基、n-己-2-炔-1-基、n-己-2-炔-4-基、n-己-2-炔-5-基、n-己-2-炔-6-基、n-己-3-炔-1-基、n-己-3-炔-2-基、3-甲基戊-1-炔-1-基、3-甲基戊1-炔-3-基、3-甲基戊-1-炔-4-基、3-甲基戊-1-炔-5-基、4-甲基戊-1-炔-1-基、4-甲基戊-2-炔-4-基或4-甲基戊-2-炔-5-基;
-C2-C6-链烯基和(C2-C6-链烯基氧基)羰基的链烯基部分:乙烯基或提到的C3-C6-链烯基的基团之一;
-(C2-C6-炔基氧基)羰基的炔基部分:乙炔基或提到的C3-C6-炔基的基团之一;
-C1-C6-烷氧基和C1-C6-烷氧基-C1-C6-烷基、(C1-C6-烷氧基)羰基和(C1-C6-烷氧基)羰基-C1-C6-烷基的烷氧基部分:甲氧基、乙氧基、n-丙氧基、1-甲基乙氧基、n-丁氧基、1-甲基丙氧基、2-甲基丙氧基或1,1-二甲基乙氧基、n-戊氧基、1-甲基丁氧基、2-甲基丁氧基、3-甲基丁氧基、1,1-二甲基丙氧基、1,2-二甲基丙氧基、2,2-二甲基丙氧基、1-乙基丙氧基、n-己氧基、1-甲基戊氧基、2-甲基戊氧基、3-甲基戊氧基、4-甲基戊氧基、1,1-二甲基丁氧基、1,2-二甲基丁氧基、1,3-二甲基丁氧基、2,2-二甲基丁氧基、2,3-二甲基丁氧基、3,3-二甲基丁氧基、1-乙基丁氧基、2-乙基丁氧基、1,1,2-三甲基丙氧基、1,2,2-三甲基丙氧基、1-乙基-1-甲基丙氧基或1-乙基-2-甲基丙氧基;
-C1-C6-烷硫基和(C1-C6-烷硫基)羰基的烷硫基部分:甲硫基、乙硫基、n-丙硫基、1-甲基乙硫基、n-丁硫基、1-甲基丙硫基、2-甲基丙硫基、1,1-二甲基乙硫基、n-戊硫基、1-甲基丁硫基、2-甲基丁硫基、3-甲基丁硫基、2,2-二甲基丙硫基、1-乙基丙硫基、n-己硫基、1,1-二甲基丙硫基、1,2-二甲基丙硫基、1-甲基戊硫基、2-甲基戊硫基、3-甲基戊硫基、4-甲基戊硫基、1,1-二甲基丁硫基、1,2-二甲基丁硫基、1,3-二甲基丁硫基、2,2-二甲基丁硫基、2,3-二甲基丁硫基、3,3-二甲基丁硫基、1-乙基丁硫基、2-乙基丁硫基、1,1,2-三甲基丙硫基、1,2,2-三甲基丙硫基、1-乙基-1-甲基丙硫基或1-乙基-2-甲基丙硫基;
-C1-C6-烷基亚硫酰基:甲基亚硫酰基、乙基亚硫酰基、n-丙基亚硫酰基、1-甲基乙基亚硫酰基、n-丁基亚硫酰基、1-甲基丙基亚硫酰基、2-甲基丙基亚硫酰基、1,1-二甲基乙基亚硫酰基、n-戊基亚硫酰基、1-甲基丁基亚硫酰基、2-甲基丁基亚硫酰基、3-甲基丁基亚硫酰基、2,2-二甲基丙基亚硫酰基、1-乙基丙基亚硫酰基、1,1-二甲基丙基亚硫酰基、1,2-二甲基丙基亚硫酰基、n-己基亚硫酰基、1-甲基戊基亚硫酰基、2-甲基戊基亚硫酰基、3-甲基戊基亚硫酰基、4-甲基戊基亚硫酰基、1,1-二甲基丁基亚硫酰基、1,2-二甲基丁基亚硫酰基、1,3-二甲基丁基亚硫酰基、2,2-二甲基丁基亚硫酰基、2,3-二甲基丁基亚硫酰基、3,3-二甲基丁基亚硫酰基、1-乙基丁基亚硫酰基、2-乙基丁基亚硫酰基、1,1,2-三甲基丙基亚硫酰基、1,2,2-三甲基丙基亚硫酰基、1-乙基-1-甲基丙基亚硫酰基或1-乙基-2-甲基丙基亚硫酰基;
-C1-C6-烷基磺酰基:甲基磺酰基、乙基磺酰基、n-丙基磺酰基、1-甲基乙基磺酰基、n-丁基磺酰基1-甲基丙基磺酰基、2-甲基丙基磺酰基、1,1-二甲基乙基磺酰基、n-戊基磺酰基、1-甲基丁基磺酰基、2-甲基丁基磺酰基、3-甲基丁基磺酰基、2,2-二甲基丙基磺酰基、1-乙基丙基磺酰基、1,1-二甲基丙基磺酰基、1,2-二甲基丙基磺酰基、n-己基磺酰基、1-甲基戊基磺酰基、2-甲基戊基磺酰基、3-甲基戊基磺酰基、4-甲基戊基磺酰基、1,1-二甲基丁基磺酰基、1,2-二甲基丁基磺酰基、1,3-二甲基丁基磺酰基、2,2-二甲基丁基磺酰基、2,3-二甲基丁基磺酰基、3,3-二甲基丁基磺酰基、1-乙基丁基磺酰基、2-乙基丁基磺酰基、1,1,2-三甲基丙基磺酰基、1,2,2-三甲基丙基磺酰基、1-乙基-1-甲基丙基磺酰基或1-乙基-2-甲基丙基磺酰基;
-C1-C6-亚烷基氨氧基:异乙炔氨氧基(Acetylidenaminoxy)、1-亚丙基氨氧基、2-亚丙基氨氧基、1-亚丁基氨氧基、2-亚丁基氨氧基或2-亚己基氨氧基;
-C3-C6-环烷基:环丙基、环丁基、环戊基或环己基;
-C3-C8-环烷基:环丙基、环丁基、环戊基、环己基、环庚基或环辛基;
-C3-C8-环烷氧基:环丙氧基、环丁氧基、环戊氧基、环己氧基、环庚氧基或环辛氧基;
3-7元杂环的例子是环氧乙基、氮杂环丙烯基(Aziridiny),氧杂环丁基(Oxetanyl)、四氢呋喃基、四氢噻吩基、吡咯烷基、异噁唑烷基、异噻唑烷基、吡唑烷基、噁唑烷基、噻唑烷基、咪唑烷基、如1,3-二氧戊环-2-基和1,3-二氧戊环-4-基之类的二氧戊环基、如1,3-二噁烷-2-基和1,3-二噁烷-4-基之类的二噁烷基、如1,3-二噻烷-2-基之类的二噻烷基,还有1,2,4-噁二唑烷基、1,3,4-噁二唑烷基、1,2,4-噻二唑烷基、1,3,4-噻二唑烷基、1,2,4-***烷基、1,3,4-***烷基、2,3-二氢呋喃基、2,5-二氢呋喃基、2,3-二氢噻吩基、2,5-二氢噻吩基、2,3-吡咯啉基、2,5-吡咯啉基、2,3-异噁唑啉基、3,4-异噁唑啉基、4,5-异噁唑啉基、2,3-异噻唑啉基、3,4-异噻唑啉基、4,5-异噻唑啉基、2,3-二氢吡唑基、3,4-二氢吡唑基、4,5-二氢吡唑基、2,3-二氢噁唑基、3,4-二氢噁唑基、哌啶基、四氢哒嗪基、四氢嘧啶基、四氢吡嗪基、1,3,5-四氢三嗪基和1,2,4-四氢三嗪基,
以及下列杂芳族化合物:
如2-呋喃基和3-呋喃基之类的呋喃基、如2-噻吩基和3-噻吩基的之类噻吩基、如2-吡咯基和3-吡咯基之类的吡咯基、如3-异噁唑基、4-异噁唑基和5-异噁唑基之类的异噁唑基、如3-异噻唑基、4-异噻唑基和5-异噻唑基之类的异噻唑基、如3-吡唑基、4-吡唑基和5-吡唑基之类的吡唑基、如2-噁唑基、4-噁唑基和5-噁唑基之类的噁唑基、如2-噻唑基、4-噻唑基和5-噻唑基之类的噻唑基、如2-咪唑基和4-咪唑基之类的咪唑基、如1,2,4-噁二唑-3-基、1,2,4-噁二唑-5-基和1,3,4-噁二唑-2-基之类的噁二唑基、如1,2,4-噻二唑-3-基、1,2,4-噻二唑-5-基和1,3,4-噻二唑-2-基之类的噻二唑基、如1,2,4-***-1-基、1,2,4-***-3-基和1,2,4-***-4-基之类的***基、如2-吡啶基、3-吡啶基和4-吡啶基之类的吡啶基、如3-哒嗪基和4-哒嗪基之类的哒嗪基、如2-嘧啶基、4-嘧啶基和5-嘧啶基之类的嘧啶基,还有2-吡嗪基、1,3,5-三嗪-2-基和1,2,4-三嗪-3-基,特别是吡啶基、嘧啶基、呋喃基和噻吩基。
所有的苯基和杂环环优选地是未取代的或带有一个卤素、甲基、三氟代甲基或甲氧基取代基。
关于本发明化学式I的化合物用作除草剂和/或作为具有脱叶/干燥作用的化合物,这些变量在每种情况下单独地或结合起来优选地具有以下含义:
X是通过氧与R8结合的-N(R7)-O-;
X是通过氮与R8结合的-O-N(R7)-;
Y是氧;
R1是卤素或氰基;
R2是氢、氟或氯;
R3是氨基或甲基;
R4是C1-C6-烷基、C1-C6-卤代烷基或C1-C6-烷基磺酰基,特别优选地是C1-C4-卤代烷基,特别是三氟甲基、一氯二氟甲基或五氟乙基;
R5是氢或卤素;
R6是氢或C1-C4-烷基,特别优选的是氢;
R7是氢、C1-C6-烷基、C3-C8-环烷基、C1-C6-卤代烷基、C3-C6-链烯基、C3-C6-炔基、(C1-C6-烷基)羰基、(C3-C6-链烯基)羰基、(C3-C6-炔基)羰基、(C1-C6-烷氧基)羰基、(C2-C6-链烯基氧基)羰基、(C2-C6-炔基氧基)羰基、(C1-C6-烷硫基)羰基、C1-C6-烷基氨基甲酰基,如果需要的话,上述13个基团的每一个基团有1个或2个取代基与其结合是可能的,在每种情况下这些取代基都选自于由下列基团组成的组中:
-硝基、氰基、卤素、C3-C8-环烷基、羟基、C1-C6-烷氧基、C3-C8-环烷氧基、C3-C6-链烯基氧基、C3-C6-炔基氧基、C1-C6-烷氧基-C1-C6-烷氧基、C1-C6-烷硫基、C1-C6-烷基亚硫酰基、C1-C6-烷基磺酰基、C1-C6-亚烷基氨基,
-一个-CO-Z1R9、-OCO-Z1R9或者-N(R9)R10基团,
R8是氢、C1-C6-烷基、C3-C8-环烷基、C1-C6-卤代烷基、C3-C6-链烯基或C3-C6-炔基,如果需要的话,上述5个基团的每一个基团有1个或2个取代基与其结合,在每种情况下这些取代基都选自于由以下基团组成的组中:
-硝基、氰基、卤素、C3-C8-环烷基、羟基、C1-C6-烷氧基、C3-C8-环烷氧基、C3-C6-链烯基氧基、C3-C6-炔基氧基、C1-C6-烷氧基-C1-C6-烷氧基、C1-C6-烷硫基、C1-C6-烷基亚硫酰基、C1-C6-烷基磺酰基、C1-C6-亚烷基氨氧基,
-一个-CO-Z2R11、-OCO-Z2R11或者-N(R11)R12基团,
Z1是一个化学键、氧、硫或-N(R10)-;
Z2是一个化学键、氧、硫或-N(R12)-;
R9、R11各自独立是氢、C1-C6-烷基、C3-C8-环烷基、C3-C6-链烯基、C3-C6-炔基、C1-C6-烷氧基-C1-C6-烷基或(C1-C6-烷氧基)羰基-C1-C6-烷基;或者
Z1和R9和/或Z2和R11在每种情况下共同代表通过氮结合的具有1-3个杂原子的3-7元杂环,该杂原子选自于由2个氧原子、2个硫原子和3个氮原子组成的组中,该杂环可以是饱和、部分或完全未饱和或是芳族的,并且如果需要的话,可有1-3个取代基与其结合,在每种情况下这些取代基都选自于由硝基、氰基、卤素、C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷氧基组成的组中;
R10、R12各自独立地是氢或C1-C6-烷基。
R7特别优选地是:
氢、C1-C6-烷基、C3-C8-环烷基、C1-C6-卤代烷基、C3-C6-链烯基、C3-C6-炔基、(C1-C6-烷基)羰基、(C3-C6-链烯基)羰基、(C3-C6-炔基)羰基、(C1-C6-烷氧基)羰基或C1-C6-烷基氨基甲酰基,上述10个基团的每一个基团还可带有一个以下的取代基:硝基、氰基、卤素、C3-C8-环烷基、羟基、C1-C6-烷氧基、C3-C8-环烷氧基、C3-C6-链烯基氧基、C3-C6-炔基氧基、C1-C6-烷氧基-C1-C6-烷氧基、C1-C6-烷硫基、C1-C6-烷基亚磺酰基、C1-C6-烷基磺酰基、C1-C6-亚烷基氨氧基、-CO-Z1R9、-OCO-Z1R9或-N(R9)R10基团。
R8特别优选地是:
氢、C1-C6-烷基、C3-C8-环烷基、C1-C6-卤代烷基、C3-C6-链烯基或C3-C6-炔基,最后提及的5个基团的每一个基团还可带有一个下列的取代基:硝基、氰基、卤素、C3-C8-环烷基、羟基、C1-C6-烷氧基、C3-C8-环烷氧基、C3-C6-链烯基氧基、C3-C6-炔基氧基、C1-C6-烷氧基-C1-C6-烷氧基、C1-C6-烷硫基、C1-C6-烷基亚硫酰基、C1-C6-烷基磺酰基、C1-C6-亚烷基氨氧基、-CO-Z2R11、-OCO-Z2R11或-N(R11)R12基团。
更特别优选的是化合物Ia(I式中X=-NH-O-、Y=氧、R1=氯、R2=氟、R3=氨基、R4=三氟代甲基,并且R5、R6=氢),该化合物列在下面的表1中:表1序号 R8Ia.01 HIa.02 CH3Ia.03 C2H5Ia.04 n-C3H7Ia.05 i-C3H7Ia.06 n-C4H9Ia.07 i-C4H9Ia.08 s-C4H9Ia.09 叔-C4H9Ia.10 环丙基Ia.11 环丁基Ia.12 环戊基Ia.13 环己基Ia.14 环庚基Ia.15 环辛基Ia.16 CH2CNIa.17 CH2CH2CNIa.18 CH(CH3)CNIa.19 C(CH3)2CNIa.20 C(CH3)2CH2CNIa.21 CH2ClIa.22 CH2CH2ClIa.23 CH(CH3)CH2ClIa.24 CH2CF3Ia.25 CHCl2Ia.26 CF2ClIa.27 CF3Ia.28 C2F5Ia.29 CF2HIa.30 CH2-CH=CH2Ia.31 CH(CH3)CH=CH2Ia.32 CH2-CH=CH-CH3Ia.33 CH2-CCHIa.34 CH(CH3)C≡CHIa.35 C(CH3)2C≡CHIa.36 CH2-COOHIa.37 CH2-CO-OCH3Ia.38 CH2-CO-OC2H5Ia.39 CH2-CO-O-(n-C3H7)Ia.40 CH2-CO-O-(i-C3H7)Ia.41 CH(CH3)-CO-OCH3Ia.42 CH(CH3)-CO-OC2H5Ia.43 CH(CH3)-CO-O-(n-C3H7)Ia.44 CH(CH3)-CO-O-(i-C3H7)Ia.45 CH2-COO-(CH2)2-OCH3Ia.46 CH2-COO-(CH2)2-OCH3Ia.47 CH(CH3)-COO-(CH2)2-OCH3Ia.48 CH(CH3)-COO-(CH2)2-OC2H5Ia.49 CH2-CONH2Ia.50 CH2-CONHCH3Ia.51 CH2-CONHC2H5Ia.52 CH2-CON(CH3)2Ia.53 CH(CH3)-CONH2Ia.54 CH(CH3)-CONHCH3Ia.55 CH(CH3)-CONH-环丙基Ia.56 CH(CH3)-CONHC2H5Ia.57 CH(CH3)-CON(CH3)2Ia.58 CH2-SCH3Ia.59 (CH2)2-SCH3Ia.60 (CH2)2-SC2H5Ia.61 (CH2)2-SO-CH3Ia.62 (CH2)2-SO2-CH3Ia.63 (CH2)2-环丙基Ia.64 (CH2)2-环戊基Ia.65 (CH2)2-O-N=C(CH3)2Ia.66 (CH2)3-O-N=C(CH3)2Ia.67 (CH2)2-NO2Ia.68 (CH2)2-NH2Ia.69 (CH2)2-NHCH3Ia.70 (CH2)2-NH(CH3)2Ia.71 CH2-OCH3Ia.72 CH(CH3)-OCH3Ia.73 CH(CH3)-OC2H5Ia.74 CH(CH3)CH2-OCH3Ia.75 (CH2)2OHIa.76 CH2-OC2H5Ia.77 CH2CO-O-(4-乙酰氧基四氢呋喃基)Ia.78 CH2-OCOCH3Ia.79 CH2-OCOC2H5Ia.80 CH2-C6H5Ia.81 (CH2)2-C6H5Ia.82 CH2-(4-Cl-C6H4)Ia.83 CH2-(4-CF3-C6H4)Ia.84 CH2-(3-NO2-C6H4)
其它非常特别优选的化学式I的苄基羟基胺是下列的化合物:
另外更:
另外更特别优选的化合物是化合物Ii(I式中Y=氧、R1=氯、R2=氟、R3=氨基、R4=三氟甲基、R5、R6=氢、R8=甲基),该化合物列在下面的表2中:表2序号 R7Ii.01 CH3Ii.02 C2H5Ii.03 n-C3H7Ii.04 i-C3H7Ii.05 n-C4H9Ii.06 i-C4H9Ii.07 s-C4H9Ii.08 叔-C4H9Ii.09 环丙基Ii.10 环丁基Ii.11 环戊基Ii.12 环己基Ii.13 环庚基Ii.14 环辛基Ii.15 CH2CNIi.16 CH2CH2CNIi.17 CH(CH3)CNIi.18 C(CH3)2CNIi.19 C(CH3)2CH2CNIi.20 CH2ClIi.21 CH2CH2ClIi.22 CH(CH3)CH2ClIi.23 CH2CF3Ii.24 CH2-CH=CH2Ii.25 CH(CH3)CH=CH2Ii.26 CH2-CH=CH-CH3Ii.27 CH2-CCHIi.28 CH(CH3)C≡CHIi.29 C(CH3)2C≡CHIi.30 CH2-COOHIi.31 CH2-CO-OCH3Ii.32 CH2-CO-OC2H5Ii.33 CH2-CO-O-(n-C3H7)Ii.34 CH2-CO-O-(i-C3H7)Ii.35 CH(CH3)-CO-OCH3Ii.36 CH(CH3)-CO-OC2H5Ii.37 CH(CH3)-CO-O-(n-C3H7)Ii.38 CH(CH3)-CO-O-(i-C3H7)Ii.39 CH2-COO-(CH2)2-OCH3Ii.40 CH2-COO-(CH2)2-OCH3Ii.41 CH(CH3)-COO-(CH2)2-OCH3Ii.42 CH(CH3)-COO-(CH2)2-OC2H5Ii.43 CH2-CONH2Ii.44 CH2-CONHCH3Ii.45 CH2-CONHC2H5Ii.46 CH2-CON(CH3)2Ii.47 CH(CH3)-CONH2Ii.48 CH(CH3)-CONHCH3Ii.49 CH(CH3)-CONHC2H5Ii.50 CH(CH3)-CON(CH3)2Ii.51 CH2-SCH3Ii.52 (CH2)2-SCH3Ii.53 (CH2)2-SC2H5Ii.54 (CH2)2-SO-CH3Ii.55 CH(CH3)-SO2-CH3Ii.56 (CH2)2-SO2-CH3Ii.57 (CH2)2-环丙基Ii.58 (CH2)2-环戊基Ii.59 (CH2)2-O-N=C(CH3)2Ii.60 (CH2)3-O-N=C(CH3)2Ii.61 (CH2)2-NO2Ii.62 (CH2)2-NH2Ii.63 (CH2)2-NHCH3Ii.64 (CH2)2-NH(CH3)2Ii.65 CH2-OCH3Ii.66 CH(CH3)-OCH3Ii.67 CH(CH3)-OC2H5Ii.68 CH(CH3)CH2-OCH3Ii.69 (CH2)2OHIi.70 CH2-OC2H5Ii.71 CH2CO-O-(4-乙酰氧基四氢呋喃-3-基)Ii.72 CH2-OCOCH3Ii.73 CH2-OCOC2H5Ii.74 CH2-C6H5Ii.75 (CH2)2-C6H5Ii.76 COOHIi.77 CO-O-CH3Ii.78 CO-O-C2H5Ii.79 CO-O-(n-C3H7)Ii.80 CO-O-(i-C3H7)Ii.81 CO-O-(n-C4H9)Ii.82 CO-O-(i-C4H9)Ii.83 CO-O-(s-C4H9)Ii.84 CO-O-(叔-C4H9)Ii.85 COO-环丙基Ii.86 COO-环丁基Ii.87 COO-环戊基Ii.88 COO-环己基Ii.89 COO-环庚基Ii.90 COO-环辛基Ii.91 COO-CH2CNIi.92 COO-CH2CH2CNIi.93 COO-CH(CH3)CNIi.94 COO-C(CH3)2CNIi.95 COO-C(CH3)2CH2CNIi.96 COO-CH2ClIi.97 COO-CH2CH2ClIi.98 COO-CH(CH3)CH2ClIi.99 COO-CH2CF3Ii.100 COO-CHCl2Ii.101 COO-CF2ClIi.102 COO-CF3Ii.103 COO-C2F5Ii.104 COO-CF2HIi.105 COO-CH2-CH=CH2Ii.106 COO-CH(CH3)CH=CH2Ii.107 COO-CH2-CH=CH-CH3Ii.108 COO-CH2-C≡CHIi.109 COO-CH(CH3)C≡CHIi.110 COO-C(CH3)2C≡CHIi.111 COO-CH2-COOHIi.112 COO-CH2-CO-OCH3Ii.113 COO-CH2-CO-OC2H5Ii.114 COO-CH2-CO-O-(n-C3H7)Ii.115 COO-CH2-CO-O-(i-C3H7)Ii.116 COO-CH(CH3)-CO-OCH3Ii.117 COO-CH(CH3)-CO-OC2H5Ii.118 COO-CH(CH3)-CO-O-(n-C3H7)Ii.119 COO-CH(CH3)-CO-O-(i-C3H7)Ii.120 COO-CH2-COO-(CH2)2-OCH3Ii.121 COO-CH2-COO-(CH2)2-OCH3Ii.122 COO-CH(CH3)-COO-(CH2)2-OCH3Ii.123 COO-CH(CH3)-COO-(CH2)2-OC2H5Ii.124 COO-CH2-CONH2Ii.125 COO-CH2-CONHCH3Ii.126 COO-CH2-CONHC2H5Ii.127 COO-CH2-CON(CH3)2Ii.128 COO-CH(CH3)-CONH2Ii.129 COO-CH(CH3)-CONHCH3Ii.130 COO-CH(CH3)-CONHC2H5Ii.131 COO-CH(CH3)-CON(CH3)2Ii.132 COO-CH2-SCH3Ii.133 COO-(CH2)2-SCH3Ii.134 COO-(CH2)2-SC2H5Ii.135 COO-(CH2)2-SO-CH3Ii.136 COO-(CH2)2-SO2-CH3Ii.137 COO-(CH2)2-SO-CH3Ii.138 COO-(CH2)2-环丙基Ii.139 COO-(CH2)2-环戊基Ii.140 COO-(CH2)2-O-N=C(CH3)2Ii.141 COO-(CH2)3-O-N=C(CH3)2Ii.142 COO-(CH2)2-NO2Ii.143 COO-(CH2)2-NH2Ii.144 COO-(CH2)2-NHCH3Ii.145 COO-(CH2)2-NH(CH3)2Ii.146 COO-CH2-OCH3Ii.147 COO-CH(CH3)-OCH3Ii.148 COO-CH(CH3)-OC2H5Ii.149 COO-CH(CH3)CH2-OCH3Ii.150 COO-(CH2)2OHIi.151 COO-CH2-OC2H5Ii.152 COO-CH2CO-O-(4-乙酰氧基四氢呋喃-3-基)Ii.153 COO-CH2-OCOCH3Ii.154 COO-CH2-OCOC2H5Ii.155 COO-CH2-C6H5Ii.156 COO-(CH2)2-C6H5Ii.157 COO-CH2-(4-Cl-C6H4)Ii.158 COO-CH2-(4-CF3-C6H4)Ii.159 COO-CH2-(3-NO2-C6H4)Ii.160 CHOIi.161 CO-CH3Ii.162 CO-C2H5Ii.163 CO-(n-C3H7)Ii.164 CO-(i-C3H7)Ii.165 CO-(n-C4H9)Ii.166 CO-(i-C4H9)Ii.167 CO-(s-C4H9)Ii.168 CO-(叔-C4H9)Ii.169 CO-环丙基Ii.170 CO-环丁基Ii.171 CO-环戊基Ii.172 CO-环己基Ii.173 CO-环庚基Ii.174 CO-环辛基Ii.175 CO-CH2CNIi.176 CO-CH2CH2CNIi.177 CO-CH(CH3)CNIi.178 CO-C(CH3)2CNIi.179 CO-C(CH3)2CH2CNIi.180 CO-CH2ClIi.181 CO-CH2CH2ClIi.182 CO-CH(CH3)CH2ClIi.183 CO-CH2CF3Ii.184 CO-CHCl2Ii.185 CO-CF2ClIi.186 CO-CF3Ii.187 CO-C2F5Ii.188 CO-CF2HIi.189 CO-CH2-CH=CH2Ii.190 CO-CH(CH3)CH=CH2Ii.191 CO-CH2-CH=CH-CH3Ii.192 CO-CH2-C≡CHIi.193 CO-CH(CH3)C≡CHIi.194 CO-C(CH3)2C≡CHIi.195 CO-CH2-COOHIi.196 CO-CH2-CO-OCH3Ii.197 CO-CH2-CO-OC2H5Ii.198 CO-CH2-CO-O-(n-C3H7)Ii.199 CO-CH2-CO-O-(i-C3H7)Ii.200 CO-CH(CH3)-CO-OCH3Ii.201 CO-CH(CH3)-CO-OC2H5Ii.202 CO-CH(CH3)-CO-O-(n-C3H7)Ii.203 CO-CH(CH3)-CO-O-(i-C3H7)Ii.204 CO-CH2-COO-(CH2)2-OCH3Ii.205 CO-CH2-COO-(CH2)2-OCH3Ii.206 CO-CH(CH3)-COO-(CH2)2-OCH3Ii.207 CO-CH(CH3)-COO-(CH2)2-OC2H5Ii.208 CO-CH2-CONH2Ii.209 CO-CH2-CONHCH3Ii.210 CO-CH2-CONHC2H5Ii.211 CO-CH2-CON(CH3)2Ii.212 CO-CH(CH3)-CONH2Ii.213 CO-CH(CH3)-CONHCH3Ii.214 CO-CH(CH3)-CONHC2H5Ii.215 CO-CH(CH3)-CON(CH3)2Ii.216 CO-CH2-SCH3Ii.217 CO-(CH2)2-SCH3Ii.218 CO-(CH2)2-SC2H5Ii.219 CO-(CH2)2-SO-CH3Ii.220 CO-(CH2)2-SO2-CH3Ii.221 CO-(CH2)2-SO-CH3Ii.222 CO-(CH2)2-环丙基Ii.223 CO-(CH2)2-环戊基Ii.224 CO-(CH2)2-O-N=C(CH3)2Ii.225 CO-(CH2)3-O-N=C(CH3)2Ii.226 CO-(CH2)2-NO2Ii.227 CO-(CH2)2-NH2Ii.228 CO-(CH2)2-NHCH3Ii.229 CO-(CH2)2-NH(CH3)2Ii.230 CO-CH2-OCH3Ii.231 CO-CH(CH3)-OCH3Ii.232 CO-CH(CH3)-OC2H5Ii.233 CO-CH(CH3)CH2-OCH3Ii.234 CO-(CH2)2OHIi.235 CO-CH2-OC2H5Ii.236 CO-CH2CO-O-(4-乙酰氧基四氢呋喃-3-基)Ii.237 CO-CH2-OCOCH3Ii.238 CO-CH2-OCOC2H5Ii.239 CO-CH2-C6H5Ii.240 CO-(CH2)2-C6H5Ii.241 CO-CH2-(4-Cl-C6H4)Ii.242 CO-CH2-(4-CF3-C6H4)Ii.243 CO-CH2-(3-NO2-C6H4)
更特别优选的苄基羟基胺I还是以下的化合物:
-化合物Ik.98-Ik.243,它们与相应的化合物Ii.01-Ii.243不同只是R1是氰基:
-化合物In.01-In.243,它们与相应的化合物Ii.01-Ii.243不同只是R3是甲基:
-化合物Io.01-Io.243,它们与相应的化合物Ii.01-Ii.243不同只是R1是氰基,而R3是甲基:
-化合物Ip.01-Ip.243,它们与相应的化合物Ii.01-Ii.243不同只是R2是氢、并且R3是甲基:
另外非常特别优选的化合物Ir(I式中Y=氧、R1=氯、R3=甲基、R4=三氟代甲基、R5和R6=氢、)列在下表3中:表3
序号 | R2 | R7 | R8 |
Ir.01 | F | CH3 | H |
Ir.02 | F | C2H5 | H |
Ir.03 | F | CH(CH3)2 | H |
Ir.04 | F | CH3 | CH3 |
Ir.05 | F | C2H5 | CH3 |
Ir.06 | F | CO-CH3 | H |
Ir.07 | F | CO-CH3 | CH3 |
Ir.08 | F | CO-OCH3 | H |
Ir.09 | F | CO-OCH3 | CH3 |
序号 | R2 | R7 | R8 | |
Ir.10 | F | CO-OC2H5 | H | |
Ir.11 | F | CO-OC2H5 | CH3 | |
Ir.12 | F | CO-CH2-CO-OC2H5 | H | |
Ir.13 | F | CO-CH2-CO-OC2H5 | CH3 | |
Ir.14 | F | SO2-CH3 | H | |
Ir.15 | F | SO2-CH3 | CH3 | |
Ir.16 | F | CH2-CO-OCH3 | H | |
Ir.17 | F | CH2-CO-OCH3 | CH3 | |
Ir.18 | F | CH2-CH=C(Cl)-CO-OCH3 | H | |
Ir.19 | F | CH2-CH=C(Cl)-CO-OCH3 | CH3 | |
Ir.20 | F | CO-CH2-CO-OCH2-CH=CH2 | H | |
Ir.21 | F | CO-CH2-CO-OCH2-CH=CH2 | CH3 | |
Ir.22 | F | CO-CH2-CO-NH-CH3 | H | |
Ir.23 | F | CO-CH2-CO-N(CH3)-CH2-CO-OCH3 | H | |
Ir.24 | H | CH3 | H | |
Ir.25 | H | C2H5 | H | |
Ir.26 | H | CH(CH3)2 | H | |
Ir.27 | H | CH3 | CH3 | |
Ir.28 | H | C2H5 | CH3 | |
Ir.29 | H | CO-CH3 | H | |
Ir.30 | H | CO-CH3 | CH3 | |
Ir.31 | H | CO-OCH3 | H | |
Ir.32 | H | CO-OCH3 | CH3 | |
Ir.33 | H | CO-OC2H5 | H | |
Ir.34 | H | CO-OC2H5 | CH3 | |
Ir.35 | H | CO-CH2-CO-OC2H5 | H | |
Ir.36 | H | CO-CH2-CO-OC2H5 | CH3 | |
Ir.37 | H | SO2-CH3 | H | |
Ir.38 | H | SO2-CH3 | CH3 | |
Ir.39 | H | CH2-CO-OCH3 | H | |
Ir.40 | H | CH2-CO-OCH3 | CH3 | |
Ir.41 | H | CH2-CH=C(Cl)-CO-OCH3 | H | |
Ir.42 | H | CH2-CH=C(Cl)-CO-OCH3 | CH3 | |
Ir.43 | H | CO-CH2-CO-OCH2-CH=CH2 | H | |
Ir.44 | H | CO-CH2-CO-OCH2-CH=CH2 | CH3 | |
Ir.45 | H | CO-CH2-CO-NH-CH3 | H | |
Ir.46 | H | CO-CH2-CO-N(CH3)-CH2-CO-OCH3 | H |
最后,非常特别优选的苄基羟基胺I还是下列化合物:
-化合物It.0-It.46,它们与相应的化合物Ir.01-Ir.46不同只是R3是氨基:
化学式I的苄基羟基胺能够通过不同的方法获得,例如通过下列方法中的一种方法获得:
方法A)
在碱存在下,化学式IV的烯胺酯或化学式V的烯胺羧酸酯被环化:
L1是低分子量烷基,优选地是C1-C4-烷基,或苯基。
一般说来,该环化作用是在一种非质子传递惰性有机溶剂或稀释剂中进行,例如在诸如1,2-二甲氧基乙烷、四氢呋喃和二噁烷之类的脂族醚或环醚中进行,在如苯和甲苯之类的芳香化合物中进行,或者在如二甲基甲酰胺和二甲亚砜的极性溶剂中进行。极性溶剂与如n-己烷之类的一种烃的混合物也是合适的。取决于原料化合物,水也可能作为稀释剂。
优选地,合适的碱是碱金属醇化物,特别是醇化钠、碱金属氢氧化物,特别是氢氧化钠和氢氧化钾、碱金属碳酸盐,尤其是碳酸钠和碳酸钾、和金属氢化物,尤其是氢化钠。当使用氢化钠作为碱时,已证明在脂族醚或环醚中,在二甲基甲酰胺或在二甲亚砜中实施该方法是有利的。
以IV或V的量计,0.5-2倍摩尔量的碱对于成功地实施该方法通常是足够的。
一般地,反应温度是(-78)℃至所述反应混合物的沸点,特别是从(-60℃)至60℃。
如果化学式IV或V中的R3是氢,该方法的产物以金属盐得到,而该金属对应于所使用碱的阳离子。这种盐可采用本身已知的方法进行分离和纯化,或者如果需要的话,可以用酸将这种盐转化为其中R3=氢的游离化合物I。
方法B)
合适的甲基化剂实例是卤代甲烷,优选的是氯代甲烷、碘代甲烷或溴代甲烷以及硫酸二甲酯、甲烷磺酸酯(甲磺酸甲酯)、甲基苯磺酸酯、甲烷-对-甲苯基磺酸酯(甲苯磺酸甲酯)、甲烷-对-溴苯磺酸酯(对溴苯磺酸甲酯)、三氟甲磺酸甲酯(methyltriflate)和重氮甲烷。
一般说来,该方法是在一种惰性有机溶剂中进行的,例如在诸如低级醇之类的一种质子传递溶剂中,优选地在乙醇(如果需要以一种与水的混合物的形式)中进行,或者在一种非质子传递溶剂中,如在一种脂族醚或环醚中,优选地在1,2-二甲氧基乙烷、四氢呋喃和二噁烷中进行,在一种脂族酮中,优选地在丙酮中进行,在一种酰胺中,优选地在二甲基甲酰胺中进行,在一种亚砜中,优选地在二甲亚砜中进行,在一种如四甲基脲和1,3-二甲基四氢2(1H)-嘧啶酮之类的脲中进行,在一种如乙酸乙酯之类的羧酸酯中进行,或者在一种如二氯甲烷和氯苯的卤代脂族烃或芳族烃中进行。
合适的碱是无机碱,例如诸如碳酸钠和碳酸钾之类的碳酸盐、如碳酸氢钠和碳酸氢钾之类的碳酸氢盐,或者如氢化钠和氢化钾之类的碱金属氢化物,和有机碱,例如诸如三乙胺、吡啶和N,N-二乙基苯胺之类的胺,或者如甲醇钠、乙醇钠和叔丁醇钾之类的碱金属醇化物。
在每种情况下以原料化合物的量为基,碱和甲基化剂的量优选地是0.5-2倍摩尔量。
通常,反应温度是从0℃直到反应混合物的沸点,优选地是0-60℃。
一种优选方法的方案包括化学式I盐的甲基化,该盐是根据方法A)环化IV(R3=H)或V(R3=H),不用从反应混合物中分离所获得的,该反应混合物还含有过量的碱,如氢化钠、乙醇钠或碳酸钠。
如果它们不能在碱性条件下直接通过如方法A)所描述的环化进行制备,那些其中R3是氢的化合物I的盐还能够用一种本来已知的方法从方法A)的产物获得。为此,例如用其中R3是氢的苄基羟基胺I处理一种无机或有机碱的含水溶液。该盐通常在如20-25℃这样的温度下就能足够迅速地生成。
在20-25℃下将苄基羟基胺I(R3=氢)溶解在氢氧化钠水溶液中制备其钠盐是特别有利的,其中所使用的苄基羟基胺与氢氧化钠的量大致是等当量的。然后例如可以通过用合适的惰性溶剂进行沉淀或通过溶剂蒸发将苄基羟基胺的盐分离。
其金属离子不是一种碱金属离子的苄基羟基胺I(R3=H)的盐通常能够通过相应的碱金属盐在含水溶液中复分解进行制备。能够用这种方法制备的化合物例如是不溶于水的苄基羟基胺金属盐。
方法C)
至今已证明特别有用的一种胺化剂是2,4-二硝基苯氧基胺,但是例如羟胺-O-磺酸(HOSA)也可以使用,它作为一种胺化剂在文献中已公开(例如,参见,E.Hofer等人,Synthesis 1983,466;W.Friedrichsen等人,Heterocycles 20(1983)1271;H.Hart等人,Tetrahedron Lett.25(1984)2073;B.Vercek等人,Monat sh.Chem.114(1983)789;G.Sosnousky等人,Z.Naturforsch.38(1983)884;R.S.Atkinson等人,J.Chem.Soc.PerkinTrans.1987,2787)。
胺化作用可以用一种本来已知的方法进行(例如参见,T.Sheradsky,Tetrahedron Lett.1968,1909;M.P.Wentland等人,J.Med.Chem.27(1984)1103以及,特别是EP-A 240 194,EP-A 476 697,EP-A 517 181和WO95/06641,这些文献说明了尿嘧啶的胺化作用)。
该反应一般是在一种极性溶剂中进行的,如在二甲基甲酰胺、N-甲基吡咯烷酮、二甲亚砜中进行,或在乙酸乙酯中进行,乙酸乙酯已被证明是迄今为止特别合适的。
合适碱的实例是如碳酸钾之类的碱金属碳酸盐、如甲醇钠和叔丁醇钾之类的碱金属醇化物,或者如氢化钠之类的碱金属氢化物。
在每种情况下,碱和胺化剂的量优选地是以原料化合物的量为基准计为0.5-2倍摩尔量。
取决于R7和R8的含义,以一种本来已知的方法保护这些取代基不胺化可能是必要的。如果R7或R8是氢,这种保护受到特别推荐。
方法D)
这种硫化作用通常在一种惰性溶剂或稀释剂中进行,例如在一种如甲苯或二甲苯之类的芳族烃中进行,在一种如***、1,2-二甲氧基乙烷和四氢呋喃之类的醚中进行,或在如吡啶之类的有机胺中进行。
作为硫化剂特别合适的是硫化磷(V)和2,4-双(4-甲氧基苯基)-1,3,2,4-二噻二磷庚烷(dithiadiphosphetan)-2,4-二硫酮(“Lawesson试剂”)
通常,以被硫化的原料化合物为基准计1-5倍摩尔量足以基本完成该反应。
反应温度通常地为20-200℃,优选地是从40℃到反应混合物的沸点。
方法E)
其中R7是氢的化学式I苄基羟基胺在碱存在下烷基化或酰化:
烷基化例如可以用卤化物进行,优选地是氯化物或溴化物、硫酸酯、磺酸酯,优选地是甲烷磺酸酯(甲磺酸酯)、苯磺酸酯、对-甲苯磺酸酯(甲苯磺酸酯)、对溴苯磺酸酯(对溴苯磺酸酯)、三氟甲磺酸酯(triflat)或一种未取代或取代的烷烃、环烷烃、卤代烷烃、烯烃或炔烃的二唑化合物。
合适的酰化剂是,如酰基卤,特别是酰基氯,酸酐、异氰酸酯类和取代或未取代烷烃-、环烷烃-、烯烃-、炔烃-或苯基羧酸的磺酰氯。另外,如果该方法是在如羰基二咪唑和二环己基碳化二亚胺之类的缩合剂存在下进行,那么这些游离酸或它们的酐是合适的。
该方法通常是在惰性有机溶剂中进行的,优选地在一种非质子传递溶剂中进行,例如诸如1,2-二甲氧基乙烷、四氢呋喃和二噁烷之类的脂族醚或环醚,一种如丙酮之类的脂族酮,一种如二甲基甲酰胺之类的酰胺,一种如二甲基亚砜之类的亚砜,一种如四甲基脲之类的脲和1,3-二甲基四氢-2(1H)-嘧啶酮,一种如乙酸乙酯之类的羧酸酯,一种如二氯甲烷和氯苯之类的卤代脂族烃或芳族烃。
合适的碱是无机碱。如碳酸钠和碳酸钾之类的碱金属碳酸盐,如碳酸氢钠和碳酸氢钾之类的碱金属碳酸氢盐,或者如氢化钠和氢化钾之类的碱金属氢化物,还可以是有机碱,如三乙基胺、吡啶和N,N-二乙基苯胺之类的胺,或者是如甲醇钠、乙醇钠和叔丁醇钾之类的碱金属醇化物。
以其中R7=氢的化学式I化合物的量为基准计,碱和烷基化剂的量优选地是0.5-2倍摩尔量。
通常,反应温度是从0℃到反应混合物的沸点,特别推荐0-60℃。
在其中R3=氢的原料化合物情况下可能出现与配向性相关的问题能够采用本身已知的方法予以避免(使用2当量碱,引入保护基团等)。
方法F)
合适的还原剂实例是如甲硼烷配合物之类的氢化物,如甲硼烷-二甲硫或甲硼烷-吡啶配合物,还有如三乙基硅烷和二苯基甲基硅烷之类的硅烷,或者分子氢(同时使用如炭上铂之类的催化剂)。
如果使用氢,建议在酸性条件下进行该反应,如以有机或无机酸作为溶剂。
氢的压力通常是从大气压到约10巴的过压。
通常,该还原反应是在(-5)至+50℃下成功进行的。
还原剂的量并不关键。该方法能够用以VII的量为基准计较少量的还原剂进行,也可以用过量还原剂,至多约15倍摩尔量。优选地,使用以肟基化合物VII为基准计0.5-2倍摩尔量的还原剂。
方法G)
进行这种裂解使用质子酸作为催化剂是很合适的。通常,以化合物VIII的量为基准计0.5-2倍摩尔量的酸将是足够的。合适的酸的实例是如乙酸之类的有机酸和如硫酸和盐酸之类的无机酸。
该反应能够直接在酸或在如甲苯之类的惰性溶剂中进行。
有利地在一种如羟胺和甲胲之类肟的存在下进行这种裂解,在这种情况下,以化合物VIII的量为基准计肟的使用量是约等摩尔量或过量至多20倍摩尔量。
通常,反应温度推荐为从0℃到反应混合物的沸点。
一般说来,在一种惰性溶剂/稀释剂中与所希望的亚烷基氨基氢氧化物HO-N=C(Ra,Rb)进行反应。如果IX以苄基卤(IXa)使用,在如三乙胺之类的有机碱或如碳酸钠和碳酸钾之类的无机碱存在下实施该方法是较为合适的。相反地,如果用苄醇(IXb)作为原料,需要如碳化二咪唑之类的缩合辅助剂。
合适的溶剂实例是如甲苯和二甲苯之类的芳族化合物、如乙酸乙酯之类的酯、如***和四氢呋喃之类的醚、如二氯甲烷之类的卤代脂族化合物或如吡啶和二甲基甲酰胺之类的碱性溶剂。
化合物IX和亚烷基氨基氢氧化物按约化学计算量使用是合适的,或者进行本方法时一种反应物或另一种反应物使用量至多过量约10摩尔%。
通常,该反应是从0℃至反应混合物沸点的温度下进行的。
方法H)
该方法优选地在如碳化二咪唑之类的缩合助剂存在下进行,碳化二咪唑的量通常是以IXa的量为基准计为0.5-2倍摩尔量。
通常,该反应是在一种惰性有机溶剂中进行的,例如像甲苯和二甲苯之类的烃、如乙酯乙酸之类的酯或如***和四氢呋喃之类的醚。
IXa和Xa以接近化学计算量使用是合适的,或一种或另一种反应剂使用稍过量,至多约10摩尔%。
通常,反应温度推荐为从0℃至反应混合物的沸点。
方法K)
卤化作用通常是在一种惰性有机溶剂或稀释剂中进行的。对于氯化作用和溴化作用例如是如乙酸之类的脂族羧酸,或如二氯甲烷、氯仿和四氯化碳之类的卤代脂族碳氢化合物。对于碘化作用特别优选低沸点的脂族羧酸,如乙酸。
特别合适的氯化剂和溴化剂是元素氯和溴,要不然是磺酰氯或磺酰溴,其反应温度优选地是0-60℃,更优选地是10-30℃。
如果需要的话,氯化作用和溴化作用可以在一种酸结合剂的存在下进行,特别优选的酸结合剂是乙酸钠和叔胺如三乙胺、二甲苯胺和吡啶。
特别优选的碘化剂是元素碘,在这种情况下反应温度是从约0℃到110℃,优选地是10-30℃。
该碘化作用特别有利地是在如发烟硝酸之类的无机酸的存在下进行的。
卤化剂的量不是关键的;通常使用等摩尔量的卤化剂,或以原料化合物(式中R5=氢的I)为基准计卤化剂过量至多约200摩尔%。
例如在反应后可以用饱和的亚硫酸氢钠水溶液除去过量碘。
方法L)
L2是卤素或较低级的烷基磺酸酯、较低级卤代烷基磺酸酯或苯磺酸酯,它们可以被取代。
通常,该方法是在惰性有机溶剂中进行的,合适的溶剂特别是非质子传递溶剂,如脂族醚或环醚,优选地是如1,2-二甲氧基乙烷、四氢呋喃和二噁烷,优选地如丙酮之类的脂族酮,优选地如二甲基甲酰胺之类的酰胺,优选地如二甲亚砜之类的亚砜如四甲基脲之类的脲和1,3-二甲基四氢-2(1H)-嘧啶酮,如乙酸乙酯之类的羧酸酯,或者如二氯甲烷和氯苯之类的卤代脂族烃或芳族烃。
合适的碱是无机碱,如碱金属碳酸盐,尤其是碳酸钠和碳酸钾之类的碳酸盐,如碱金属碳酸氢盐,尤其是碳酸氢钠和碳酸氢钾之类的碳酸氢盐,或者是如氢化钠和氢化钾之类的碱金属氢化物,而且还有有机碱,如三乙胺、吡啶和N,N-二乙基苯胺之类的胺,或者是如甲醇钠、乙醇钠和叔丁醇钾之类的碱金属醇化物。
通常在每种情况下碱和烷基化剂XI的量以X的量为基准计为0.5-2倍摩尔量。
通常,该反应是在(-78)℃到反应混合物沸点下进行的,特别是在(-60℃)至60℃进行的。
XII XIII IV
该方法优选地是在惰性溶剂或稀释剂中在基本无水的条件下进行的,特别优选地是在酸性或碱性催化剂存在下进行的。
合适的溶剂或稀释剂特别是可与水形成共沸混合物的有机溶剂,例如诸如苯、甲苯和二甲苯之类的芳族化合物,如二氯甲烷、氯仿、四氯化碳和氯苯之类的卤代烃,如1,2-二甲氧基乙烷、四氢呋喃和二噁烷之类的脂族醚或环醚或环己烷,还有如甲醇和乙醇之类的醇。
优选地合适的酸性催化剂是强无机酸如硫酸和盐酸,如正磷酸和多磷酸之类的含磷的酸,如对甲苯磺酸之类的有机酸,和如“Amberlyst 15”(由Fluka生产)之类的酸性阳离子交换剂。
合适的碱性催化剂是,例如诸如氢化钠之类的金属氢化物,以及特别优选地如甲醇钠和乙醇钠之类的金属醇化物。
XIII和β-酮酯XII以大致化学计算量使用是合适的,或该方法以一种组分或另一种组分稍过量至多约10摩尔%进行实施。
以原料化合物中的一种化合物的量为基准计,0.5-2倍摩尔量的催化剂通常是足够的。
通常,该反应是在60-120℃下进行的,优选地在反应混合物的沸点下进行,以迅速除去生成的水。
XIV XIII IVL3是C1-C4-烷基或苯基。
该反应能够例如在一种可与水混溶的惰性有机溶剂中进行,例如在诸如1,2-二甲氧基乙烷、四氢呋喃和二噁烷之类的脂族醚或环醚,或一种较低的醇,特别是乙醇中进行,该反应温度通常是50-100℃,优选地是反应混合物的沸点。
但是,该反应还可在一种如苯、甲苯和二甲苯之类的芳族稀释剂中进行,在这种情况下加入一种如盐酸和对甲苯磺酸之类的酸性催化剂,或加入一种碱,例如诸如甲醇钠和乙醇钠之类的碱金属醇化物是可取的。在这个方案中,反应温度通常也是50-100℃,但优选的是60-80℃。
关于量的比例问题,方法M)所给出的资料在这里也是适用的。
XV XVI IV
该反应在一种基本无水的非质子传递的有机溶剂或稀释剂存在的下进行是合适的,例如象***、1,2-二甲氧基乙烷、四氢呋喃和二噁烷之类的脂族醚或环醚,如n-己烷、苯、甲苯和二甲苯之类的脂族或芳族烃,如二氯甲烷、氯仿、四氯化碳、1,2-二氯乙烷之类的卤代脂族烃和氯苯,如二甲基甲酰胺、六甲基磷酸三酰胺和二甲亚砜之类的非质子传递极性溶剂,或它们的混合物。
如果需要,该方法还可以在以下化合物存在下进行,如氢化钠和氢化钾之类的金属氢化物碱,如甲醇钠、乙醇钠和叔丁醇钾之类的碱金属醇化物或碱土金属醇化物,或如三乙胺和吡啶之类的有机叔胺碱,这些有机碱可同时起溶剂的作用。
原料化合物以化学计算量使用,或者一种组分或另一种组分稍微过量至多约10摩尔%是合适的。若该方法在有一种有机碱而没有溶剂的情况下实施时,建议使用大大过量的有机碱。
反应温度(-80℃)至50℃,特别是(-60)至30℃通常是足够的。
在一个特别优选的实例中,根据方法A)使用过量的碱将生成的烯胺酯IV直接转化(即“就地”)为相应的所希望的产物I。能够通过如结晶和色谱法之类的通常分离方法除去任何的副产物(如在R3=氢的化合物情况下,C-烷基化产物)。
P):
XV XVII IV
L4是C1-C4-烷基或苯基。
该反应有利地在一种非质子传递的极性溶剂或稀释剂中进行,如二甲基甲酰胺、2-丁酮、二甲亚砜和乙腈,宜在碱存在下进行,例如碱金属醇化物或碱土金属醇化物,尤其是如甲醇钠之类的链烷醇钠,一种碱金属碳酸盐或碱土金属碳酸盐,尤其是碳酸钠,或如氢化锂和氢化钠之类的碱金属氢化物。
以XV或XVII的量为基准计,0.5-2倍摩尔量的碱通常是足够的。
该反应温度通常是80-180℃,优选的是反应混合物的沸点。
至于原料化合物的比率,可以参照方法M)所给出的资料。
在一个特别优选的实例中,使用醇化钠作为碱,在反应过程中生成的醇连续不断被蒸馏掉。以这种方法制备的烯胺酯IV可以无需由该反应混合物分离而按照方法A)进行环化,得到相应的苄基羟基胺I的盐。
XVIII XIX IV
该反应有利地是在一种基本无水的非质子传递有机溶剂或稀释剂中进行的,例如象***、1,2-二甲氧基乙烷、四氢呋喃和二噁烷之类的脂族醚或环醚,如n-己烷、苯、甲苯和二甲苯之类的脂族烃或芳族烃,如二氯甲烷、氯仿、四氯化碳、1,2-二氯乙烷之类的卤代脂族烃和氯苯,如二甲基甲酰胺、六甲基磷酸三酰胺和二甲亚砜之类的非质子传递的极性溶剂,或在它们的混合物存在下进行。
如果需要的话,该方法还可以在以下碱存在的情况下进行,如氢化钠和氢化钾之类的金属氢化物,如甲醇钠、乙醇钠和叔丁醇钾之类的碱金属醇化物或碱土金属醇化物,或如三乙胺和吡啶之类的有机氮碱,该有机碱可以同时起到溶剂的作用。
以化学计算量使用原料化合物或以过量至多约20摩尔%的量使用这些组分中的一种组分是合适的。如果该方法是在有一种有机碱而没有溶剂的情况下进行的,则使用较大过量的有机碱是有利的。
反应温度通常为(-80℃)至150℃,优选地是(-30℃)至所述反应混合物的沸点。
化学式V的烯胺羧酸酯也是新的;它们也能通过本来已知的方法制备,例如可按照下述反应方案R)由一种化学式XV的苯胺衍生物制备:
XX与XIX的反应优选地是在一种无水惰性非质子传递溶剂中进行的,例如在如二氯甲烷、氯仿、四氯化碳和氯苯之类的卤代烃中,在如苯、甲苯和二甲苯之类的芳族烃中,在一种如***、丁醚、1,2-二甲氧基乙烷、四氢呋喃和二噁烷之类的脂族醚或环醚中进行。
该反应(XX与XIX的反应)的反应温度通常是约70-140℃,特别是100-120℃。
XII与XIX的反应是一种氨基分解反应,它通常是在无溶剂的情况下[例如可参看,J.Soc.Dyes Col.,42,81(1926),Ber.64,970(1931);Org.Synth.,Coll.Vol.IV,80(1963)和J.Am.Chem.Soc.70,2402(1948)]或在一种惰性无水溶剂/稀释剂中进行的,尤其在一种非质子传递溶剂中进行,例如在一种如甲苯和二甲苯之类的芳族化合物中,或者在一种如氯苯之类的卤代芳族化合物中进行。
建议在一种碱性催化剂存在下,例如一种高沸点胺[例如参见,Helv.Chim.Acta 11,779(1928)和U.S.2,416,738]或吡啶存在下实施该方法。
该反应温度优选地是约20-160℃。
在所有情况下以大致化学计算量使用原料化合物是有利的,否则一种或另外一种组分以稍微过量至多约10摩尔%的量实施该方法。如果该方法是在一种碱性催化剂存在下进行的,以其中一种原料的量为基准计0.5-2倍摩尔量的催化剂通常是足够的。
胺HN(R3)-COOL1与所生成的化学式XXI化合物的后续反应有利地是在一种基本无水的溶剂/稀释剂中在大气压下进行的,特别优选地是在一种酸性催化剂存在下进行的。
为了制备其中R3=氨基的烯胺羧酸酯V,建议使用带有一个已保护氨基的化合物XXII(如一种腙)。
合适的溶剂/稀释剂特别是能够与水混合得到一种共沸混合物的有机液体,例如如苯、甲苯和二甲苯之类的芳族化合物,或如四氯化碳和氯苯之类的卤代烃。
合适的催化剂特别是如硫酸之类的强无机酸,如对甲苯磺酸之类的有机酸、如正磷酸和多磷酸之类的含磷的酸,或如“Amberlyst 15”(由Fluka生产)之类的酸性阳离子交换剂。
反应温度通常为约70-150℃;但是,为了迅速除去反应生成的水,该方法有利地是在所述反应混合物沸点下进行的。
化学式XIII、XVI、XVII和XXI的化合物也都是新的。它们也可以用一种本来已知的方法制备,特别有利地是由化学式XIX的化合物制备:S):化学式XIX化合物“光气化作用”和用氨水解该方法产物XVI(衍生物):
该方法可在一种基本无水的惰性溶剂/稀释剂中或在没有溶剂的情况下进行的。优选地采用光气或氯甲酸三氯甲基酯将该氨基转化为异氰酸酯基团。
合适的溶剂/稀释剂特别是非质子传递的有机溶剂,例如象甲苯和二甲苯之类的芳族化合物,如二氯甲烷、氯仿、1,2-二氯乙烷和氯苯之类的卤代烃,如1,2-二甲氧基乙烷、四氢呋喃和二噁烷之类的脂族醚或环醚,如乙酸乙酯之类的酯,和它们的混合物。
取决于所使用的苯胺衍生物XIX,可能有利的是加入一种如三乙基胺之类的碱,加入量例如是以XIX的量为基准计为0.5-2倍摩尔数。
异氰酸苯酯XVI通常是在50℃至该反应混合物沸点的温度下生成的;它们能够接着与氨或与可反应的氨的衍生物反应得到苯基脲衍生物XIII。
T):与碱金属氰酸盐的反应
M+是当量金属离子,特别是碱金属离子,如钠和钾离子。
该反应通常在一种惰性溶剂/稀释剂中进行,例如在如甲苯和二甲苯之类的芳族烃中,在如四氢呋喃和二噁烷之类的脂族醚或环醚中,在如甲醇和乙醇之类的较低级的醇中,在水中,或在它们的混合物中进行。
氰酸盐的量不是关键的;但是,完成反应需要至少等摩尔量的苯胺化合物XIX和氰酸盐;但是,氰酸盐过量至多约100摩尔%可能也是有利的。
反应温度通常为0℃至反应混合物的沸点。
L5是卤素,优选地是氯或溴、C1-C4-烷氧基或苯氧基。
合适的溶剂/稀释剂例如是,如甲苯和二甲苯之类的芳族烃,如二氯甲烷、氯仿、1,2-二氯乙烷和氯苯之类的卤代烃,如1,2-二甲氧基乙烷、四氢呋喃和二噁烷之类的脂族醚或环醚,如乙酸乙酯之类的酯,如甲醇和乙醇之类的醇或水。一种有机溶剂和水的混合物也是合适的。
该方法优选地是在一种碱的存在下进行的,例如在如氢氧化钠、碳酸钠、甲醇钠和乙醇钠之类的碱金属氢氧化物、碱金属碳酸盐或碱金属醇化物,或如吡啶和三乙基胺之类的叔胺存在下进行的。
如果需要的话,也可以加入一种催化剂,例如如三氯化锑之类的路易斯酸。
以大致化学计算量使用原料化合物和碱是有利的,但是一种组分或其它的组分也可以过量至多约100摩尔%。
催化剂的量以使用的苯胺化合物XIX的量为基准计通常是1-50摩尔%,优选地是2-30摩尔%。
该反应在从(-40)℃至反应混合物的沸点的温度下通常可成功地实施。
XXIV XVII(X=-NH-O-)
化学式XXIII的硝基化合物也是新的。它们能够通过本来已知的方法合成得到,例如通过使相应的苄胺硝化合成得到。
化学式VII、X、XI、XII、XIV、XV、XVIII、XIX和XXIV的化合物都是已知的或能够采用本来已知的方法合成得到的(例如参见,WO 92/02088和DE-A 42 37 920)。
除非另外指出,所有上述方法在大气压下,或在所述反应混合物的固有压力下进行都是合适的。
取决于目标化合物的取代类型,改变单个反应步骤的顺序以不生成或少量生成某种副产物是可取的。
通常通过本来已知的方法处理该反应混合物,例如通过除去溶剂,使残余物分配在水与一种合适的有机溶剂的混合物中,然后处理该有机相以得到产物。
化学式I的苄基羟基胺可以含有一个或更多的手性中心,除非调整该合成方法以得到一种特定的异构体,通常都是以对映体或非对映体混合物的形式得到该苄基羟基胺。如果希望的话,可以采用为此惯用的方法分离该混合物,例如通过结晶或用旋光吸附物色谱分离得到基本纯的异构体。纯的旋光异构体还可以例如由相应的旋光原料物质制备。
可采用本来已知的方法将其中R3、R7、或R8是氢的苄基羟基胺转化成其盐,优选地是它们的碱金属盐。
其金属离子不是碱金属离子的I的盐可采用惯用的方法通过相应碱金属盐的复分解反应制备出来,铵、鏻、锍和氧化锍盐可以用氨、氢氧化鏻氢氧化锍或氧化锍氢氧化物制备得到。
化合物I及其农业上有用的盐适合作为除草剂,它们可以是异构体混合物的形式和纯异构体的形式。包含I的除草组合物在控制非耕地的植物方面非常有效,特别是在高施用量的情况下。它们可以在作物如小麦、稻、玉米、大豆和棉花中防治阔叶杂草和禾草,而不对作物造成明显的伤害。这种效果特别是出现在低施用量的情况下。
考虑到施用方法的多样性,化合物I或含有它的组合物也可以用于许多其它作物,用于消灭莠草。适合的作物的实例是下列作物:洋葱、凤梨、花生、芦笋、甜菜(Beta vulgaris spp.altissima)、芜菁甜菜(Beta vulgaris spp.rapa)、Brassica napus var.napus、Brassica napus var.napobrassica、蔓菁(Brassica rapa var.silvestris)、茶、红花、美洲山核桃、柠檬、甜橙、小果咖啡(中果咖啡、大果咖啡)、黄瓜、狗牙根、胡萝卜、油棕、欧洲草莓、大豆、陆地棉、(鸡脚棉、草棉、Gossypium vitifolium)、向日葵、巴西橡胶、大麦、啤酒花、甘蓝、核桃、兵豆、亚麻、蕃茄、苹果属、木薯、紫花苜蓿、芭蕉属、烟草(黄花烟草)、油橄榄、稻、雪豆、菜豆、欧洲云杉、松属、豌豆、欧洲甜樱桃、桃、西洋梨、红醋栗、蓖麻、甘蔗、黑麦、马铃薯、芦黍(蜀黍)、可可、红车轴草、普通小麦、硬粒小麦、蚕豆、葡萄、玉米。
此外,化合物I也可以应用在这样的作物上,所述作物通过育种包括基因工程的方法,业已对除草剂的作用具有高抗性。
此外式I的苄基羟胺同样适合于植物的干燥和/脱叶。
作为干燥,它特别适合于干燥农作物如土豆、芸苔、向日葵和大豆的地上部分。因此使得这些重要农作物的完全机械化的收割是可能的。
由于短时的集中下落或对柑果、橄榄和其他种类的干果和核果来说在树木上的附着强度的降低使收割更容易在经济上是很有意义的。同样的机理,即促进植物果实或叶片与茎之间分离组织的形成同样对于很好地控制经济作物,特别是棉花的落叶是重要的。
此外,单个棉花作物成熟的时间间隔的缩短导致在收获之后高的纤维强度。
化合物I或含该化合物的制剂例如可以以可直接喷洒的水溶液、粉末、悬浮液、高浓度的水、油或其他悬浮液或分散液、乳液、油分散液、膏剂、撒粉剂、撒布用剂或颗粒的形式通过喷洒、喷雾、雾化、撒布或浇注使用。使用形式取决于应用目的;在任何情况下应该保证本发明的活性物质尽可能细的分散。
用于制备可直接喷雾溶液、乳剂、膏剂或油分散液的惰性助剂一般是中等至高沸点的石油馏分如煤油和柴油,煤焦油以及来源于植物和动物的油类,脂族、环状和芳族烃例如石蜡、四氢化萘、烷基化的萘和其衍生物,烷基化的苯和其衍生物,醇类如甲醇、乙醇、丙醇、丁醇和环己醇,酮如环己酮,强极性溶剂例如胺如N-甲基吡咯烷酮和水。
含水的使用形式是由乳油、悬浮液、膏剂、可湿性粉末或可以用水分散的颗粒通过添加水而制备的。为了制备乳液、膏剂或油分散液,该基质本身或其溶解在油或溶剂中,借助于润湿剂、粘附剂、分散剂或乳化剂在水中均化。然而同样可以由活性物质、润湿剂、粘附剂、分散剂或乳化剂和可能的话溶剂或油制备适合于用水稀释的浓缩物。
适合的表面活性物质是芳族磺酸例如木质素磺酸、苯酚磺酸、萘磺酸和二丁基萘磺酸以及脂肪酸的碱金属盐、碱土金属盐、铵盐,烷基磺酸盐和烷芳基磺酸盐,烷基-、十二烷基醚-和脂肪醇硫酸盐,以及硫酸化的十六烷基醇、十七烷基醇和十八烷基醇以及脂肪醇乙二醇醚的盐,磺化的萘和其衍生物与甲醛的缩合产物,萘或萘磺酸与苯酚和甲醛的缩合产物,聚氧乙烯辛基苯酚醚,乙氧基化异辛基-、辛基-或壬基苯酚,烷基苯基-、三丁基苯基聚乙二醇醚,烷芳基聚醚醇,异十三烷基醇、脂肪醇氧化乙烯缩合物,乙氧基化蓖麻油,聚氧乙烯或聚氧丙烯烷基醚,十二烷基醇聚乙二醇醚乙酸酯,山梨醇酯、木素亚硫酸盐废液或甲基纤维素。
粉剂、撒粉剂和撒布剂可以通过活性物质与固态载体的混合或混磨来制备。
颗粒剂例如包衣、浸渍和匀质颗粒可以通过将活性物质粘合在固态载体上来制备。固态载体是矿质土类如硅酸、硅胶、硅酸盐、滑石、高岭土、石灰石、石灰、白垩、红玄武土、黄土、陶土、白云石、硅藻土、硫酸钙和硫酸镁、氧化镁、磨细的塑料、肥料,如硫酸铵、磷酸铵、硝酸铵、尿素和植物产品如谷类作物粉末、树皮、木材和核桃壳粉,纤维素粉末或其他固态载体。
活性物质I在即可使用的制剂中的浓度可以在较宽的范围内变化。一般所使用的制剂包含约0.001~98重量%、优选0.01~95重量%的至少一种活性物质。活性物质的纯度是90~100%,优选95~100%(根据NMR-光谱)。
下面配制剂的实施例说明这种制剂的制备:
I、将20重量份的序号It.10的化合物溶解在一种混合物中,该混合物由80重量份的烷基化苯、10重量份的8~10摩尔氧化乙烯在1摩尔油酸-N-单乙醇酰胺上的加成产物、5重量份的十二烷基苯磺酸的钙盐和5重量份的40摩尔氧化乙烯在1摩尔蓖麻油上的加成产物组成。通过将溶液倾入100000重量份的水中并细分散得到一种水分散液,其包含0.02重量%的活性物质。
II、将20重量份的序号1.02的化合物溶解在一种混合物中,该混合物由40重量份的环己酮、30重量份的异丁醇、20重量份7摩尔氧化乙烯在1摩尔异辛基苯酚上的加成产物和10重量份的40摩尔氧化乙烯在1摩尔蓖麻油上的加成产物组成。通过将溶液倾入100000重量份的水中并细分散得到一种水分散液,其包含0.02重量%的活性物质。
III、将20重量份的序号1.03的化合物溶解在一种混合物中,该混合物由25重量份的环己酮、65重量份的沸点为210~280℃的石油馏分和10重量份的40摩尔氧化乙烯在1摩尔蓖麻油上的加成产物组成。通过将该溶液倾入100000重量份的水中并细分散得到一种水分散液,其包含0.02重量%的活性物质。
IV、将20重量份的序号1.05的化合物与3重量份的二异丁基萘-α-磺酸的钠盐、17重量份来自亚硫酸盐废液的木素磺酸的钠盐和60重量份的粉状硅胶均匀地混合,并在锤磨机中粉磨。通过该混合物在20000重量份水中的均匀分散得到一种喷洒混合物,其包含0.1重量%的活性物质。
V、将3重量份的序号1.04的活性物质与97重量分的细高岭土混合。按照这种方式得到一种撒粉剂,其包含3重量%的活性物质。
VI、将20重量份的序号1.16的活性物质与2重量份的十二烷基苯磺酸钙、8重量份的脂肪醇-聚乙二醇醚、2重量份的苯酚-尿素-甲醛缩合物的钠盐和68重量份的石蜡质的矿物油均匀地混合。得到一种稳定的油分散液。
VII、将1重量份的序号1.17的活性物质溶解在一种混合物中,该混合物由70重量份的环己酮、20重量份的乙氧基化的异辛基苯酚和10重量份的乙氧基化的蓖麻油组成。得到一种稳定的乳油。
VIII、将1重量份的序号1.18的活性物质溶解在一种混合物中,该混合物由80重量份的环己酮和20重量份的Uniperol_EL(=基于乙氧基化蓖麻油的非离子乳化剂)组成。得到一种稳定的乳油。
活性物质I或除草组合物的使用可以在苗前或苗后进行。如果这种活性物质对某种农作物是较不耐受的,那么可以采用这样喷洒技术,其中在喷洒设备的帮助下喷洒该除草剂,以便尽可能地不要喷洒到敏感性农作物的叶片上,同时活性物质到达生长于其下的的不希望的植物的叶片上或到达未覆盖的土表上(苗后直接处理、铺施)。
根据防治目标、季节、靶体植物和生长阶段的不同,活性物质的施用量是0.001~3.0,优选0.01~1.0kg/ha活性物质(a.s.)。
为了扩展作用谱和得到协同的效果,苄基羟胺I可以与众多的具有代表性的其他除草剂或生长调节活性物质混合和一起使用。例如可以作为混合组分的是1,2,4-噻二唑类、1,3,4-噻二唑类,酰胺类、氨基磷酸类和其衍生物,氨基***类,N-酰苯胺类、芳氧基-/杂芳基氧基链烷酸类和其衍生物、苯甲酸和其衍生物、苯并噻二嗪酮类、2-(杂芳酰基/芳酰基)-1,3-环己二酮类、杂芳基-芳基-酮类、苄基异噁唑烷酮类、间-CF3-苯基衍生物、氨基甲酸酯类、喹啉羧酸和其衍生物、氯乙酰苯胺类、环己-1,3-二酮衍生物、二嗪类、二氯丙酸和其衍生物、二氢苯并呋喃类、二氢呋喃-3-酮类、二硝基苯胺类、二硝基苯酚类、二苯基醚类、联吡啶类、卤代羧酸和其衍生物、脲类、3-苯基尿嘧啶类、咪唑类、咪唑啉酮类、N-苯基-3,4,5,6-四氢邻苯二甲酰亚胺类、噁二唑类、环氧乙烷类、苯酚类、芳氧基-和杂芳氧基苯氧基丙酸酯类、苯基乙酸和其衍生物、2-苯基丙酸和其衍生物、吡唑类、苯基吡唑类、哒嗪类、吡啶羧酸和其衍生物、嘧啶基醚类、磺酰胺类、磺酰脲类、三嗪类、三嗪酮类、***啉酮类、***甲酰胺类和尿嘧啶类。
此外,有利的是化合物I单独或与其他的除草剂一起与其他的作物保护剂混合使用,例如与灭害虫或植物病原真菌或细菌的制剂一起使用。此外,有意义的是与无机盐溶液的可混合性,采用这种方法来消除营养和微量元素的缺乏。同样可以加入无植物毒性的油和油的浓缩物。
制备实施例
实施例1
3-(4-氯-3-甲氧基氨基甲基苯基)-1-甲基-6-三氟甲基-1,2,3,4-四氢嘧啶-2,4-二酮(1.01号化合物)
将三乙基硅烷(1.9毫升)滴加到3-(4-氯-3-甲氧基亚氨基甲基苯基)-1-甲基-6-三氟甲基-1,2,3,4-四氢嘧啶-2,4-二酮(3.6克)在30毫升二氯甲烷和50毫升三氟乙酸混合物中的溶液里。该混合物在室温下搅拌20小时后蒸去溶剂。其残留物被收集到200毫升二氯甲烷中,之后每次用50毫升水洗涤有机相共四次,经硫酸钠干燥并最终将其浓缩。用二异丙醚和石油醚结晶得到标题化合物(熔点为83-85℃)。
实施例2
3-(4-氯-3-乙氧基氨基甲基苯基)-1-甲基-6-三氟甲基-1,2,3,4-四氢嘧啶-2,4-二酮(1.02号化合物)
甲硼烷-吡啶配合物(3毫升)和10%盐酸(30毫升)在0℃下相继滴加到3-(4-氯-3-乙氧基亚氨基甲基苯基)-1-甲基-6-三氟甲基-1,2,3,4-四氢嘧-2,4-二酮(3.8克)在40毫升乙醇中的溶液里。在16小时内,另加入12毫升甲硼烷-吡啶配合物。接着该溶液在回流温度下搅拌4小时,之后蒸去溶剂。其残留物被收集到200毫升的二氯甲烷中。每次用50毫升水洗涤有机相共洗两次,然后经硫酸钠干燥,并最终将其浓缩。这样得到一种油状的标题化合物。
实施例3
3-(3-[乙酰基(甲氧基氨基)甲基]-4-氯代苯基)-1-甲基-6-三氟甲基-1,2,3,4-四氢嘧啶-2,4-二酮(1.04号化合物)
将3-(4-氯-3-甲氧基氨基甲基苯基)-1-甲基-6-三氟甲基-1,2,3,4-四氢嘧啶-2,4-二酮(在30毫升四氢呋喃中有1.6克)滴加到氢化钠(在50毫升四氢呋喃中有0.17克)悬浮液中。一小时后,加入乙酰氯(在20毫升四氢呋喃中有0.4克)。该混合物在室温下搅拌20小时,接着用水(100毫升)处理。用2×100毫升二氯甲烷从水相中萃取所需要的产物。合并的有机相用水洗涤三次,经硫酸钠干燥并除去溶剂。硅胶色谱分离(洗脱液:二氯甲烷/乙酸乙酯=9∶1)和用石油醚结晶可得到标题化合物(熔点为160-161℃)。
实施例4
3-(3-[(甲氧基甲基氨基)甲基]-4-氯代苯基)-1-甲基-6-三氟甲基-1,2,3,4-四氢嘧啶-2,4-二酮(1.06号化合物)
将3-(3-溴代甲基)-4-氯-2-氟苯基)-1-甲基-6-三氟甲基-1,2,3,4-四氢嘧啶-2,4-二酮(0.005摩尔)加到甲氧基甲胺(0.06摩尔)、碳酸钾(0.012摩尔)和100毫升二甲基甲酰胺的混合物中。在室温下5小时后浓缩该反应溶液。其残留物用100毫升二氯甲烷处理,之后每次用30毫升水洗涤有机相共三次,然后经硫酸钠干燥并最终将其浓缩。通过加入石油醚由得到的油可获得所需要的目标产物。
实施例5
3-(3-[乙氧基羰基氨氧基甲基]-4-氯-6-氟代苯基)-1-氨基-6-三氟甲基-1,2,3,4-四氢嘧啶-2,4-二酮(It.10号化合物)
将0.9克羰基二咪唑加入1.8克3-(3-羟甲基-4-氯-6-氟苯基)-1-氨基-6-三氟甲基-1,2,3,4-四氢嘧啶-2,4-二酮在100毫升四氢呋喃中的溶液里。该反应混合物搅拌1小时后,加入0.58克N-乙氧基羰基羟基胺。接着该混合物在20℃下再搅拌14小时,之后蒸馏除去其溶剂。将其残留物收集到100毫升二氯甲烷中。用水洗涤得到的有机相,然后经硫酸钠干燥并最终浓缩。通过硅胶色谱法(洗脱液:二氯甲烷)纯化粗制产物。产量:0.2克。
除了上述的化合物,在下表4中列出了其它苄基羟基胺I,它们已经或能够通过相似方法进行制备:表4
序号 Y R1 R2 R3 R4 R5 R6 R7 R8 熔点[℃] |
1.01 O Cl H CH3 CF3 H H H CH3 83-851.02 O Cl H CH3 CF3 H H H C2H5 油1.03 O Cl H CH3 CF3 H H COOC2H5 CH3 油1.04 O Cl H CH3 CF3 H H COCH3 CH3 160-1611.05 O Cl F NH2 CF3 H H H CH3 63-671.06 O Cl H CH3 CF3 H H CH3 CH31.07 O Cl F NH2 CF3 H H CH3 H 153-1551.08 O Cl F NH2 CF3 H H COOCH3 CH3 112-1151.09 O Cl F NH2 CF3 H H COCH3 CH3 119-1211.10 O Cl F NH2 CF3 H H COCHCl2 CH3 122-1251.11 O Cl F NH2 CF3 H H CO-环丙基 CH3 85-891.12 O Cl F NH2 CF3 H H CH3 CH3 油1.13 O Cl F NH2 CF3 H H COCH2OCOCH3CH3 90-941.14 O Cl F NH2 CF3 H H COSCH3 CH3 113-1201.15 O Cl F NH2 CF3 H H COC2H5 CH3 133-1361.16 O Cl F NH2 CF3 H H COOC2H5 CH3 115-1171.17 O Cl F NH2 CF3 H H COCF3 CH3 162-1641.18 O Cl F NH2 CF3 H H CONH-C6H5 CH3 138-143 |
应用实施例(除草效果)
苄基羟基胺I的除草作用通过下述温室试验说明:
所用的栽培容器是塑料花盆,盆中装有腐殖质含量约为3.0%的壤砂土作为基质。根据不同的种类,分别播种不同试验植物的种子。
在苗前处理的情况下,在播种后,将悬浮或乳化于水中的活性化合物用分布性能良好的喷嘴直接施用。花盆稍微浇些水,以促使萌发和生长,然后,覆盖上透明塑料地膜,直到植物生根。如果不是受活性化合物影响的话,覆盖应会使试验植物均匀的萌发。
进行苗后处理时,先让试验植物长出,根据不同的生长形式,让其长到3至15cm高,此时方用悬浮或乳化于水中的活性化合物处理。对于这种目的,试验植物或是直接播种并在同一花盆中生长,或是先以秧苗分别生长,再在处理前几天,将它们移栽到试验花盆中。苗后处理的施用量是0.0156、0.0078、0.0039或0.0019kg/ha a.S.(活性物质)。
根据种类的不同,将植物放置在10-25℃或20-35℃下。试验期历经2至4周。在此期间,悉心照料植物,并评价它们对各处理的反应。
以0至100的等级进行评分。在此情况下,100是指没有植物出苗或至少完全毁灭地上部分,而0是指无伤害或生长正常。
在温室中使用的植物是由下列品种组成的:
拉丁名 | 德语名 | 中文 |
Abutilon theophrasti | Chinesischer Hanf | 苘麻 |
Galium aparine | Klettenlabkraut | 猪秧秧 |
Sinapis alba | WeiBer Senf | 欧白芥 |
Solanum nigrum | Schwarzer Nachtschatten | 龙葵 |
Veronica subspecies | Ehrenpreisarten | 婆婆纳 |
以每公顷0.0156或0.0078千克的活性组分施用量,1.03号化合物当苗后使用时对苘麻、龙葵和各种婆婆纳属品种表现出很好的除草作用。
以每公顷3.9或1.9克的活性组分施用量,It.10号化合物当苗后使用时对猪秧秧、欧白芥和龙葵表现出很好的除草作用。应用实施例(干燥/脱叶效果)
使用4叶(无子叶)棉花植物幼苗作为试验用植物,其在温室条件下生长(相对空气湿度50~70%;白天/夜晚温度27/20℃)。
使用活性物质(以喷射液计添加0.15重量%的脂肪醇烷氧基化物Plurafac LF 700)的含水处理液进行棉花植物幼苗的叶片处理至滴水点。使用的水量为1000升/ha(换算)。在13天之后测定叶子脱落的数目和脱叶的程度(%)。
未处理的对照植物无脱叶现象。
Claims (16)
1.一种化学式I的苄基羟基胺式中变量具有下面的含义:
X是-N(R7)-O-,它可通过氧或氮与R8结合;
Y是氧或硫;
R1是卤素、氰基、硝基或三氟甲基;
R2是氢或卤素;
R3是氢、氨基或甲基;
R4是氢、卤素、C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷硫基、C1-C6-烷基亚硫酰基或C1-C6-烷基磺酰基;
R5是氢、卤素或C1-C6-烷基;
R6是氢、C1-C6-烷基、C1-C6-卤代烷基、C3-C6-环烷基或C2-C6-链烯基;
R7是氢、C1-C6-烷基、C3-C8-环烷基、C1-C6-卤代烷基、C3-C6-链烯基、C3-C6-炔基、(C1-C6-烷基)羰基、(C3-C6-链烯基)羰基、(C3-C6-炔基)羰基、(C1-C6-烷氧基)羰基、(C2-C6-链烯基氧基)羰基、(C2-C6-炔基氧基)羰基、(C1-C6-烷硫基)羰基、C1-C6-烷基磺酰基、C1-C6-烷基氨基甲酰基,其中最后提及的14个基团的每一个可任选地带有1-3个取代基,这些取代基各选自于由下列基团组成的组中:
-硝基、氰基、卤素、C3-C8-环烷基、羟基、C1-C6-烷氧基、C3-C8-环烷氧基、C3-C6-链烯基氧基、C3-C6-炔基氧基、C1-C6-烷氧基-C1-C6-烷氧基、C1-C6-烷硫基、(C1-C6-烷基)羰基、(C1-C6-烷基)羰基氧基、C1-C6-烷基亚硫酰基、C1-C6-烷基磺酰基、C1-C6-亚烷基氨氧基、C1-C6-烷基氨基甲基,
-苯基、苯氧基或苯磺酰基,其中苯环可以是未被取代或带有1-3个取代基,这些取代基在每种情况下都选自于由卤素、硝基、氰基、C1-C6-烷基、C1-C6-烷氧基和C1-C6-卤代烷基组成的组中。
-一个具有1-3个杂原子的3-7元杂环或杂环氧基团,这些杂原子选自于由2个氧原子、2个硫原子和3个氮原子组成的组中,该杂环可以是饱和、部分或完全未饱和或是芳族的,并且如果需要的话,有1-3个取代基与其结合,这些取代基在每种情况下都选自于由卤素、硝基、氰基、C1-C6-烷基、C1-C6-烷氧基、C1-C6-卤代烷基和(C1-C6-烷基)羰基组成的组中,
-一个-CO-Z1R9、-OCO-Z1R9或者-N(R9)R10基团,或者
R7是C3-C8-环烷基羰基、苯基羰基、苯磺酰基或苯基氨基甲酰基,这4个基团可以未被取代或有1-3个取代基与其结合,在每种情况下这些取代基都选自于由卤素、硝基、氰基、C1-C6-烷基、C1-C6-烷氧基和C1-C6-卤代烷基组成的组中;
R8是氢、C1-C6-烷基、C3-C8-环烷基、C1-C6-卤代烷基、C3-C6-链烯基或C3-C6-炔基,如果需要的话,最后提及的5个基团中每一个基团可以有1-3个取代基与其结合,在每种情况下这些取代基都选自于由以下基团组成的组中:
-硝基、氰基、卤素、C3-C8-环烷基、羟基、C1-C6-烷氧基、C3-C8-环烷氧基、C3-C6-链烯基氧基、C3-C6-炔基氧基、C1-C6-烷氧基-C1-C6-烷氧基、C1-C6-烷硫基、C1-C6-烷基亚硫酰基、C1-C6-烷基磺酰基、C1-C6-亚烷基氨氧基,
-苯基、苯氧基或苯磺酰基,其中苯环可以是未被取代或有1-3个取代基与其结合,在每种情况下这些取代基都选自于由硝基、氰基、卤素、C1-C6-烷基、C1-C6-烷氧基和C1-C6-卤代烷基组成的组中,
-一个具有1-3个杂原子的3-7元的杂环或杂环氧基团,这些杂原子选自于由2个氧原子、2个硫原子和3个氮原子组成的组中,该杂环可以是饱和、部分或完全未饱和或是芳族的,并且如果需要的话,有1-3个取代基与其结合,在每种情况下这些取代基都选自于由卤素、硝基、氰基、C1-C6-烷基、C1-C6-烷氧基、C1-C6-卤代烷基和(C1-C6-烷基)羰基组成的组中,
-一个-CO-Z2R11、-OCO-Z2R11或者-N(R11)R12基团,
Z1是一个化学键、氧、硫或-N(R10)-;
Z2是一个化学键、氧、硫或-N(R12)-;
R9、R11相互独立地是氢、C1-C6-烷基、C1-C6-卤代烷基、C3-C8-环烷基、C3-C6-链烯基、C3-C6-炔基、C1-C6-烷氧基-C1-C6-烷基、(C1-C6-烷氧基)羰基-C1-C6-烷基、苯基或苯基-C1-C6-烷基,苯基和苯基烷基的苯环可以是未被取代或有1-3个取代基与其结合,在每种情况下这些取代基都选自于由硝基、氰基、卤素、C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷氧基或(C1-C6-烷基)羰基组成的组中,或者
Z1和R9和/或Z2和R11在每种情况下共同为一个通过氮结合的并具有1-3个杂原子的3-7元杂环,这些杂原子选自于由2个氧原子、2个硫原子和3个氮原子组成的组中,该杂环可以是饱和、部分或完全未饱和或是芳族的,并且如果需要的话,有1-3个取代基与其结合,在每种情况下这些取代基都选自于由硝基、氰基、卤素、C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷氧基组成的组中;
R10、R12相互独立地是氢、羟基、C1-C6-烷基、C3-C8-环烷基或C1-C6-烷氧基,
或者是一种其中R3、R7和/或R8是氢的化合物I的在农业上可用的盐。
2.一种如权利要求1所述的化学式I苄基羟基胺,其中变量具有下述的含义:
Y是氧;
R1是卤素或氰基;
R2是氢、氟或氯;
R3是氨基或甲基;
R4是C1-C6-烷基、C1-C6-卤代烷基或C1-C6-烷基磺酰基;
R5是氢或卤素;
R6是氢或C1-C4-烷基;
R7是氢、C1-C6-烷基、C3-C8-环烷基、C1-C6-卤代烷基、C3-C6-链烯基、C3-C6-炔基、(C1-C6-烷基)羰基、(C3-C6-链烯基)羰基、(C3-C6-炔基)羰基、(C1-C6-烷氧基)羰基、(C2-C6-链烯基氧基)羰基、(C2-C6-炔基氧基)羰基、(C1-C6-烷硫基)羰基、C1-C6-烷基氨基甲酰基,最后提及的13个基团中每个基团可任选地有1或2个取代基与其结合,在每种情况下这些取代基都选自于由下列基团组成的组中:
-硝基、氰基、卤素、C3-C8-环烷基、羟基、C1-C6-烷氧基、C3-C8-环烷氧基、C3-C6-链烯基氧基、C3-C6-炔基氧基、C1-C6-烷氧基-C1-C6-烷氧基、C1-C6-烷硫基、C1-C6-烷基亚硫酰基、C1-C6-烷基磺酰基、C1-C6-亚烷基氨氧基,以及
-一个-CO-Z1R9、-OCO-Z1R9或者-N(R9)R10基团,
R8是氢、C1-C6-烷基、C3-C8-环烷基、C1-C6-卤代烷基、C3-C6-链烯基或C3-C6-炔基,最后提及的5个基团中每个基团任选地有1或2个取代基与其结合,在每种情况下这些取代基都选自于由以下基团组成的组中:
-硝基、氰基、卤素、C3-C8-环烷基、羟基、C1-C6-烷氧基、C3-C8-环烷氧基、C3-C6-链烯基氧基、C3-C6-炔基氧基、C1-C6-烷氧基-C1-C6-烷氧基、C1-C6-烷硫基、C1-C6-烷基亚硫酰基、C1-C6-烷基磺酰基、C1-C6-亚烷基氨氧基,以及
-一个-CO-Z2R11、-OCO-Z2R11或-N(R11)R12基团,
Z1是一个化学键、氧、硫或-N(R10)-;
Z2是一个化学键、氧、硫或-N(R12)-;
R9、R11相互独立地是氢、C1-C6-烷基、C3-C8-环烷基、C3-C6-链烯基、C3-C6-炔基、C1-C6-烷氧基-C1-C6-烷基或(C1-C6-烷氧基)羰基-C1-C6-烷基;或者
Z1和R9和/或Z2和R11在每种情况下共同为通过氮结合的并具有1-3个杂原子的3-7元杂环,这些杂原子选自于由2个氧原子、2个硫原子和3个氮原子组成的组中,该杂环可以是饱和,部分或完全未饱和或是芳族的,并且如果需要的话,有1-3个取代基与其结合,在每种情况下这些取代基都选自于由硝基、氰基、卤素、C1-C6-烷基、C1-C6-卤代烷基和C1-C6-烷氧基组成的组中;
R10、R12相互独立地是氢或C1-C6-烷基。
3.根据权利要求1所述的化学式I苄基羟基胺或化合物I的在农业上有用的盐作为除草剂,或用于植物干燥和/或脱叶的应用。
4.一种除草组合物,它含有除草有效量的至少一种如权利要求1所述的化学式I的苄基羟基胺或至少一种化合物I的在农业上有用的盐,和至少一种惰性液体和/或固体载体,并且如果需要的话,还有至少一种表面活性剂。
5.一种用于植物干燥和/或脱叶的组合物,该组合物含有干燥和/或脱叶有效量的至少一种如权利要求1所述的化学式I的苄基羟基胺或至少一种化合物I的在农业上有用的盐,和至少一种惰性液体和/或固体载体,并且如果需要还有至少一种表面活性剂。
6.一种制备具有除草作用的组合物的方法,该方法包括将除草有效量的至少一种如权利要求1所述的化学式I的苄基羟基胺或至少一种化合物I的在农业上有用的盐,与至少一种惰性液体和/或固体载体,并且如果需要还有至少一种表面活性剂混合起来。
7.一种制备具有干燥和/或脱叶作用的组合物的方法,该方法包括将干燥和/或脱叶有效量的至少一种如权利要求1所述的化学式I的苄基羟基胺或至少一种化合物I的在农业上有用的盐,与至少一种惰性液体和/或固体载体,并且如果需要还有至少一种表面活性剂混合起来。
8.一种控制不希望有的植物生长的方法,该方法包括让除草有效量的至少一种如权利要求1所要求的化学式I的苄基羟基胺或至少一种化合物I的在农业上有用的盐作用于植物、它们的生长环境或种子上。
9.一种对植物干燥和/或脱叶的方法,该方法包括让干燥和/或脱叶有效量的至少一种如权利要求1所要求的化学式I的苄基羟基胺或至少一种化合物I的在农业上有用的盐作用于植物上。
10.一种化学式IV的烯胺酯
式中L1是C1-C6-烷基或苯基,取代基R1-R8具有如权利要求1所给定的含义。
12.-种化学式XIII的苯基脲衍生物
式中取代基R1-R3和R6-R8具有如权利要求1所给定的含义。
13.一种化学式XVI的异氰酸苯基酯
式中取代基R1、R2和R6-R8具有如权利要求1所给定的含义。
14.一种化学式XVII的苯胺衍生物
式中L4是C1-C4-烷基或苯基,并且取代基R1、R2和R6-R8具有如权利要求1所给定的含义。
Applications Claiming Priority (4)
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DE19524617.9 | 1995-07-06 | ||
DE1995124617 DE19524617A1 (de) | 1995-07-06 | 1995-07-06 | Benzylhydroxylamine und Zwischenprodukte zu deren Herstellung |
DE1996116719 DE19616719A1 (de) | 1996-04-26 | 1996-04-26 | Benzylhydroxylamine und Zwischenprodukte zu deren Herstellung |
DE19616719.1 | 1996-04-26 |
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CN1192737A true CN1192737A (zh) | 1998-09-09 |
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US (1) | US6057269A (zh) |
EP (1) | EP0836594B1 (zh) |
JP (1) | JPH11508574A (zh) |
KR (1) | KR19990028722A (zh) |
CN (1) | CN1192737A (zh) |
AU (1) | AU6305696A (zh) |
BR (1) | BR9609306A (zh) |
CA (1) | CA2223111A1 (zh) |
CZ (1) | CZ2698A3 (zh) |
DE (1) | DE59606553D1 (zh) |
HU (1) | HUP9802434A2 (zh) |
IL (1) | IL122686A0 (zh) |
MX (1) | MX9800081A (zh) |
PL (1) | PL324524A1 (zh) |
TR (1) | TR199800010T1 (zh) |
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DE19528186A1 (de) | 1995-08-01 | 1997-02-06 | Bayer Ag | Substituierte Phenyluracile |
DE10051981A1 (de) | 2000-10-20 | 2002-05-02 | Bayer Ag | Substituierte Phenyluracile |
WO2003029226A1 (en) * | 2001-09-26 | 2003-04-10 | Basf Aktiengesellschaft | Heterocyclyl substituted phenoxyalkyl-, phenylthioalkyl-, phenylaminoalkyl- and phenylalkyl-sulfamoylcarboxamides |
US7767624B2 (en) * | 2002-07-23 | 2010-08-03 | Basf Aktiengesellschaft | 3-Heterocyclyl substituted benzoic acid derivatives |
CN101932325B (zh) * | 2007-11-30 | 2014-05-28 | 新联基因公司 | Ido抑制剂 |
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IT1201113B (it) * | 1986-01-10 | 1989-01-27 | Fmc Corp | Composti erbicidi |
AU627906B2 (en) * | 1989-07-14 | 1992-09-03 | Nissan Chemical Industries Ltd. | Uracil derivatives and herbicides containing the same as active ingredient |
DE4131038A1 (de) * | 1991-09-20 | 1993-04-01 | Basf Ag | Substituierte 3-phenylurazile |
DE4237920A1 (en) * | 1991-11-13 | 1993-05-19 | Ciba Geigy Ag | 3-Aryl-uracil derivs. - are effective against weeds, act as dessicants, and facilitate harvesting of cotton, potato or rape |
US5336663A (en) * | 1991-11-13 | 1994-08-09 | Ciba-Geigy Corporation | 3-aryluracil derivatives and their use for weed control |
DE4329537A1 (de) * | 1993-09-02 | 1995-03-09 | Basf Ag | Substituierte 1-Amino-3-phenyluracile |
US5486521A (en) * | 1994-03-21 | 1996-01-23 | Uniroyal Chemical Company, Inc. | Pyrimidinyl aryl ketone oximes |
-
1996
- 1996-06-27 PL PL96324524A patent/PL324524A1/xx unknown
- 1996-06-27 HU HU9802434A patent/HUP9802434A2/hu unknown
- 1996-06-27 AU AU63056/96A patent/AU6305696A/en not_active Abandoned
- 1996-06-27 KR KR1019980700020A patent/KR19990028722A/ko not_active Application Discontinuation
- 1996-06-27 IL IL12268696A patent/IL122686A0/xx unknown
- 1996-06-27 CA CA002223111A patent/CA2223111A1/en not_active Abandoned
- 1996-06-27 WO PCT/EP1996/002805 patent/WO1997002253A1/de not_active Application Discontinuation
- 1996-06-27 BR BR9609306A patent/BR9609306A/pt not_active Application Discontinuation
- 1996-06-27 DE DE59606553T patent/DE59606553D1/de not_active Expired - Fee Related
- 1996-06-27 JP JP9504786A patent/JPH11508574A/ja not_active Ceased
- 1996-06-27 US US08/973,780 patent/US6057269A/en not_active Expired - Fee Related
- 1996-06-27 TR TR1998/00010T patent/TR199800010T1/xx unknown
- 1996-06-27 CN CN96196204A patent/CN1192737A/zh active Pending
- 1996-06-27 EP EP96922038A patent/EP0836594B1/de not_active Expired - Lifetime
- 1996-06-27 CZ CZ9826A patent/CZ2698A3/cs unknown
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CN105682465A (zh) * | 2013-09-18 | 2016-06-15 | 瑞戴格作物保护公司 | 农业化学品 |
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DE59606553D1 (de) | 2001-04-12 |
US6057269A (en) | 2000-05-02 |
BR9609306A (pt) | 1999-06-15 |
WO1997002253A1 (de) | 1997-01-23 |
HUP9802434A2 (hu) | 1999-01-28 |
EP0836594B1 (de) | 2001-03-07 |
AU6305696A (en) | 1997-02-05 |
PL324524A1 (en) | 1998-06-08 |
CA2223111A1 (en) | 1997-01-23 |
TR199800010T1 (xx) | 1998-05-21 |
IL122686A0 (en) | 1998-08-16 |
JPH11508574A (ja) | 1999-07-27 |
CZ2698A3 (cs) | 1998-07-15 |
MX9800081A (es) | 1998-11-29 |
KR19990028722A (ko) | 1999-04-15 |
EP0836594A1 (de) | 1998-04-22 |
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