CN1481369A - 取代的苯基尿嘧啶类化合物 - Google Patents
取代的苯基尿嘧啶类化合物 Download PDFInfo
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- CN1481369A CN1481369A CNA018209467A CN01820946A CN1481369A CN 1481369 A CN1481369 A CN 1481369A CN A018209467 A CNA018209467 A CN A018209467A CN 01820946 A CN01820946 A CN 01820946A CN 1481369 A CN1481369 A CN 1481369A
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- Prior art keywords
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- methyl
- amino
- fluorine
- chlorine
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- 150000001875 compounds Chemical class 0.000 title claims description 133
- -1 cyano, carboxy, carbamoyl Chemical group 0.000 claims abstract description 553
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 73
- 239000001257 hydrogen Substances 0.000 claims abstract description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 47
- 238000000034 method Methods 0.000 claims abstract description 36
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 34
- 150000002367 halogens Chemical group 0.000 claims abstract description 34
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 27
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 17
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 17
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 15
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 12
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- 150000002431 hydrogen Chemical group 0.000 claims abstract 25
- 239000000460 chlorine Substances 0.000 claims description 145
- 229910052801 chlorine Inorganic materials 0.000 claims description 138
- 239000011737 fluorine Substances 0.000 claims description 134
- 229910052731 fluorine Inorganic materials 0.000 claims description 134
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 118
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 117
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 63
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 46
- 239000002585 base Substances 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 36
- 238000006243 chemical reaction Methods 0.000 claims description 32
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 29
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 29
- 229910052794 bromium Inorganic materials 0.000 claims description 29
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 28
- 238000002360 preparation method Methods 0.000 claims description 27
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 18
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 17
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 17
- 125000006011 chloroethoxy group Chemical group 0.000 claims description 16
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 239000000463 material Substances 0.000 claims description 15
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 14
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 14
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 14
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 14
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 12
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 12
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 12
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- JSLZUBLGGPEVQN-DIPNUNPCSA-N (2r)-4-methyl-2-propan-2-yl-2-[2-[4-[4-[2-(3,4,5-trimethoxyphenyl)ethyl]piperazin-1-yl]butoxy]phenyl]-1,4-benzothiazin-3-one Chemical compound COC1=C(OC)C(OC)=CC(CCN2CCN(CCCCOC=3C(=CC=CC=3)[C@@]3(C(N(C)C4=CC=CC=C4S3)=O)C(C)C)CC2)=C1 JSLZUBLGGPEVQN-DIPNUNPCSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 10
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 10
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 10
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 10
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 10
- 229950001891 iprotiazem Drugs 0.000 claims description 10
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000001544 thienyl group Chemical group 0.000 claims description 10
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 9
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 8
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 8
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 claims description 8
- 125000001352 cyclobutyloxy group Chemical group C1(CCC1)O* 0.000 claims description 8
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 8
- 239000011630 iodine Substances 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 6
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 claims description 6
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 claims description 6
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 6
- 125000002757 morpholinyl group Chemical group 0.000 claims description 6
- 125000004193 piperazinyl group Chemical group 0.000 claims description 6
- 125000005936 piperidyl group Chemical group 0.000 claims description 6
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 6
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- 229920002554 vinyl polymer Polymers 0.000 claims description 6
- 229930045534 Me ester-Cyclohexaneundecanoic acid Natural products 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 230000002363 herbicidal effect Effects 0.000 claims description 5
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- ILNIKVGUHSUIEQ-UHFFFAOYSA-N (4-bromo-3-methylphenyl)carbamic acid Chemical compound CC1=CC(NC(O)=O)=CC=C1Br ILNIKVGUHSUIEQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 4
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 4
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 4
- ZRNSSRODJSSVEJ-UHFFFAOYSA-N 2-methylpentacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(C)C ZRNSSRODJSSVEJ-UHFFFAOYSA-N 0.000 claims description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- HXELGNKCCDGMMN-UHFFFAOYSA-N [F].[Cl] Chemical compound [F].[Cl] HXELGNKCCDGMMN-UHFFFAOYSA-N 0.000 claims description 4
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 4
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 4
- 125000006311 cyclobutyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000006312 cyclopentyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000006317 cyclopropyl amino group Chemical group 0.000 claims description 4
- 125000003963 dichloro group Chemical group Cl* 0.000 claims description 4
- 125000006003 dichloroethyl group Chemical group 0.000 claims description 4
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 4
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000006006 difluoroethoxy group Chemical group 0.000 claims description 4
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
- 125000006627 ethoxycarbonylamino group Chemical group 0.000 claims description 4
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052742 iron Inorganic materials 0.000 claims description 4
- 125000006629 isopropoxycarbonylamino group Chemical group 0.000 claims description 4
- 125000006229 isopropoxyethyl group Chemical group [H]C([H])([H])C([H])(OC([H])([H])C([H])([H])*)C([H])([H])[H] 0.000 claims description 4
- 125000006626 methoxycarbonylamino group Chemical group 0.000 claims description 4
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
- NBVXSUQYWXRMNV-UHFFFAOYSA-N monofluoromethane Natural products FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims description 4
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 4
- 125000006324 propenyl amino group Chemical group 0.000 claims description 4
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000006337 tetrafluoro ethyl group Chemical group 0.000 claims description 4
- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 4
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 4
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 4
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 4
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 4
- AYFMPMKATOGAGY-UHFFFAOYSA-N 1-bromo-4-isocyanato-2-methylbenzene Chemical compound CC1=CC(N=C=O)=CC=C1Br AYFMPMKATOGAGY-UHFFFAOYSA-N 0.000 claims description 3
- RGHJWZADAWEIFE-UHFFFAOYSA-N 4-amino-2-methylbenzonitrile Chemical compound CC1=CC(N)=CC=C1C#N RGHJWZADAWEIFE-UHFFFAOYSA-N 0.000 claims description 3
- MMEGELSFOYDPQW-UHFFFAOYSA-N 4-bromo-3-methylaniline Chemical compound CC1=CC(N)=CC=C1Br MMEGELSFOYDPQW-UHFFFAOYSA-N 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- 239000005864 Sulphur Chemical group 0.000 claims description 3
- 150000003863 ammonium salts Chemical class 0.000 claims description 3
- 239000010941 cobalt Substances 0.000 claims description 3
- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 2
- 159000000007 calcium salts Chemical class 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000006202 diisopropylaminoethyl group Chemical group [H]C([H])([H])C([H])(N(C([H])([H])C([H])([H])*)C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- MDQRDWAGHRLBPA-UHFFFAOYSA-N fluoroamine Chemical compound FN MDQRDWAGHRLBPA-UHFFFAOYSA-N 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims description 2
- 230000002140 halogenating effect Effects 0.000 claims description 2
- 159000000003 magnesium salts Chemical class 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000001103 potassium chloride Substances 0.000 claims description 2
- 235000011164 potassium chloride Nutrition 0.000 claims description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 2
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims 5
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract 2
- 125000006193 alkinyl group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 239000013067 intermediate product Substances 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 description 74
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 20
- 230000000694 effects Effects 0.000 description 17
- 244000025254 Cannabis sativa Species 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 241000209149 Zea Species 0.000 description 14
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 13
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 13
- 235000005822 corn Nutrition 0.000 description 13
- 239000002689 soil Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 11
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- 241000219146 Gossypium Species 0.000 description 9
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 235000010469 Glycine max Nutrition 0.000 description 6
- 244000068988 Glycine max Species 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
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- 125000004432 carbon atom Chemical group C* 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 230000012010 growth Effects 0.000 description 6
- 238000003306 harvesting Methods 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 108090000623 proteins and genes Proteins 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 230000009261 transgenic effect Effects 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- 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 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 230000006837 decompression Effects 0.000 description 5
- 239000000975 dye Substances 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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- 239000002243 precursor Substances 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
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- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
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- WQKGAJDYBZOFSR-UHFFFAOYSA-N potassium;propan-2-olate Chemical compound [K+].CC(C)[O-] WQKGAJDYBZOFSR-UHFFFAOYSA-N 0.000 description 1
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- 230000001737 promoting effect Effects 0.000 description 1
- MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 1
- OYJMHAFVOZPIOY-UHFFFAOYSA-N propan-2-yl 2-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]benzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1 OYJMHAFVOZPIOY-UHFFFAOYSA-N 0.000 description 1
- FKLQIONHGSFYJY-UHFFFAOYSA-N propan-2-yl 5-[4-bromo-1-methyl-5-(trifluoromethyl)pyrazol-3-yl]-2-chloro-4-fluorobenzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(C=2C(=C(N(C)N=2)C(F)(F)F)Br)=C1F FKLQIONHGSFYJY-UHFFFAOYSA-N 0.000 description 1
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
- FROBCXTULYFHEJ-OAHLLOKOSA-N propaquizafop Chemical compound C1=CC(O[C@H](C)C(=O)OCCON=C(C)C)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 FROBCXTULYFHEJ-OAHLLOKOSA-N 0.000 description 1
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- BBKDWPHJZANJGB-IKJXHCRLSA-N quizalofop-P-tefuryl Chemical group O=C([C@H](OC=1C=CC(OC=2N=C3C=CC(Cl)=CC3=NC=2)=CC=1)C)OCC1CCCO1 BBKDWPHJZANJGB-IKJXHCRLSA-N 0.000 description 1
- BACHBFVBHLGWSL-JTQLQIEISA-N rac-diclofop methyl Natural products C1=CC(O[C@@H](C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-JTQLQIEISA-N 0.000 description 1
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- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
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- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
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- 238000002791 soaking Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
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- ZDXMLEQEMNLCQG-UHFFFAOYSA-N sulfometuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=CC(C)=N1 ZDXMLEQEMNLCQG-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
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- HOWHQWFXSLOJEF-MGZLOUMQSA-N systemin Chemical compound NCCCC[C@H](N)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(O)=O)C(=O)OC(=O)[C@@H]1CCCN1C(=O)[C@H]1N(C(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H]2N(CCC2)C(=O)[C@H]2N(CCC2)C(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](C)N)C(C)C)CCC1 HOWHQWFXSLOJEF-MGZLOUMQSA-N 0.000 description 1
- 108010050014 systemin Proteins 0.000 description 1
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- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- RJKCKKDSSSRYCB-UHFFFAOYSA-N tebutam Chemical compound CC(C)(C)C(=O)N(C(C)C)CC1=CC=CC=C1 RJKCKKDSSSRYCB-UHFFFAOYSA-N 0.000 description 1
- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- AHTPATJNIAFOLR-UHFFFAOYSA-N thifensulfuron-methyl Chemical group S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(C)N=2)=C1C(=O)OC AHTPATJNIAFOLR-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 description 1
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-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
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 241000228158 x Triticosecale Species 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/52—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
- C07C265/12—Derivatives of isocyanic acid having isocyanate groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
- C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明涉及新的式(I)所示取代的苯基尿嘧啶类化合物,其中,R1代表氢、氨基或分别任选被取代的烷基、链烯基或炔基,R2代表氰基、羧基、氨基甲酰基、硫代氨基甲酰基或分别任选被取代的烷基或烷氧基羰基,R3代表氢、卤素或任选被取代的烷基,R4代表氢、硝基、氰基、烷氧基或卤素,R5代表氰基、硫代氨基甲酰基、卤素或分别任选被取代的烷基或烷氧基,且R6代表经由N连接的任选被取代的含氮杂环基。本发明还涉及制备所述苯基尿嘧啶类化合物的方法,所述化合物作为植物处理剂的应用,以及制备所述化合物的中间产物和方法。
Description
本发明涉及新的取代的苯基尿嘧啶类化合物、其制备方法及其作为农作物处理剂、特别是除草剂的应用。
已知有一些取代的芳基尿嘧啶类化合物具有除草活性(参见EP-A-408382/US-A-5084084/US-A-5127935/US-A-5154755,EP-A-563384,EP-A-648749,US-A-4979982,US-A-5169430,WO-A-91/00278,WO-A-97/01541,WO-A-98/41093,WO-A-00/02866)。然而,迄今为止这些化合物没有体现出任何特别重要的价值。
因此,本发明提供了新的式(I)所示取代的苯基尿嘧啶类化合物
其中
R1代表氢、氨基或分别任选被取代的烷基、链烯基或炔基,
R2代表氰基、羧基、氨基甲酰基、硫代氨基甲酰基或分别任选被取代的烷基或烷氧基-羰基,
R3代表氢、卤素或任选被取代的烷基,
R4代表氢、硝基、氰基、烷氧基或卤素,
R5代表氰基、硫代氨基甲酰基、卤素或分别任选被取代的烷基或烷氧基,且
R6代表经由N连接的任选被取代的含氮杂环基,
包括通式(I)化合物的所有可能的互变异构形式以及通式(I)化合物的可能的盐或酸或碱加合物。
在这些定义中,烃链例如烷基或烷二基分别是直链或支链的,包括在与杂原子的组合例如烷氧基中的。
在上文和下文提及的式中存在的优选取代基或取代基的优选范围定义如下。
R1优选代表氢、氨基,任选被氰基、卤素或C1-C4-烷氧基取代的具有1-4个碳原子的烷基,或分别任选被卤素取代的分别具有2-4个碳原子的链烯基或炔基。
R2优选代表氰基、羧基、氨基甲酰基、硫代氨基甲酰基,或分别任选被氰基、卤素或C1-C4-烷氧基取代的分别具有1-4个碳原子的烷基或烷氧基-羰基。
R3优选代表氢、卤素或任选被卤素取代的具有1-4个碳原子的烷基。
R4优选代表氢、硝基、氰基、C1-C4-烷氧基或卤素。
R5优选代表氰基、硫代氨基甲酰基、卤素或分别任选被卤素取代的分别具有1-4个碳原子的烷基或烷氧基。
R6优选代表经由N连接的含有1-4个选自下列的杂原子的4-12元饱和或不饱和单环或二环杂环基:氮原子、氧原子、硫原子、-SO-、-SO2-、-CO-和/或-CS-,所述杂环基可任选被下列基团取代:硝基、羟基、巯基、氨基、氰基、羧基、氨基甲酰基、卤素、C1-C4-烷基、氰基-C1-C4-烷基、羧基-C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基-C1-C4-烷基、C1-C4-烷氧基-羰基-C1-C4-烷基、C1-C4-烷基-氨基羰基-C1-C4-烷基、二-(C1-C4-烷基)-氨基羰基-C1-C4-烷基、C1-C4-烷基-羰基、C1-C4-卤代烷基-羰基、C1-C4-烷氧基-C1-C4-烷基-羰基、C1-C4-烷氧基、氰基-C1-C4-烷氧基、C1-C4-卤代烷氧基、C1-C4-烷氧基-C1-C4-烷氧基、羧基-C1-C4-烷氧基、C1-C4-烷氧基-羰基-C1-C4-烷氧基、C1-C4-烷基氨基羰基-C1-C4-烷氧基、二-(C1-C4-烷基)-氨基羰基-C1-C4-烷氧基、C1-C4-烷氧基-羰基、C2-C4-链烯氧基、C2-C4-炔氧基、C1-C4-烷硫基、C1-C4-卤代烷硫基、C1-C4-烷基亚磺酰基、C1-C4-卤代烷基亚磺酰基、C1-C4-烷基磺酰基、C1-C4-卤代烷基磺酰基、C1-C4-烷基-羰基-氨基、C1-C4-烷氧基-羰基-氨基、C1-C4-烷基-磺酰基-氨基、C2-C4-链烯基、C2-C4-卤代链烯基、C2-C4-炔基、C2-C4-链烯氧基、C2-C4-卤代链烯氧基、C2-C4-炔氧基、C2-C4-链烯硫基、C2-C4-卤代链烯硫基、C2-C4-炔硫基、C2-C4-链烯基氨基、C2-C4-炔基氨基、(分别任选被卤素取代的)C3-C6-环烷基、C3-C6-环烷氧基、C3-C6-环烷硫基、C3-C6-环烷基氨基、C3-C6-环烷基-C1-C4-烷基、C3-C6-环烷基-C1-C4-烷氧基、C3-C6-环烷基-C1-C4-烷硫基、C3-C6-环烷基-C1-C4-烷基氨基、(分别任选被硝基、氰基、卤素、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基或C1-C4-卤代烷氧基取代的)苯基、吡啶基、苯氧基、苯硫基、苯基氨基、苄基、苄氧基、苄硫基或苄基氨基。
R1特别优选代表氢、氨基,或分别任选被氰基、氟、氯、甲氧基或乙氧基取代的甲基、乙基、正或异丙基,或分别任选被氟和/或氯取代的丙烯基、丁烯基、丙炔基或丁炔基。
R2特别优选代表氰基、羧基、氨基甲酰基、硫代氨基甲酰基,或分别任选被氰基、氟、氯、甲氧基或乙氧基取代的甲基、乙基、正或异丙基、甲氧基羰基、乙氧基羰基、正或异丙氧基羰基。
R3特别优选代表氢、氟、氯、溴,或分别任选被氟和/或氯取代的甲基、乙基、正或异丙基。
R4特别优选代表氢、甲氧基、乙氧基、硝基、氰基、氟、氯或溴。
R5特别优选代表氰基、硫代氨基甲酰基、氟、氯、溴,或分别任选被氟或氯取代的甲基、乙基、正或异丙基、甲氧基、乙氧基、正或异丙氧基。
R6特别优选代表经由N连接的饱和或不饱和单环或二环含氮杂环基,所述杂环基选自:吡咯基、吡咯烷基、吡唑基、咪唑基、异噁唑烷基、三唑基、哌啶基、吗啉基、硫代吗啉基、哌嗪基,并且所述杂环基可任选被下列基团取代:硝基、羟基、巯基、氨基、氰基、羧基、氨基甲酰基、氟、氯、溴、碘、甲基、乙基、正或异丙基、正丁基、异丁基、仲丁基或叔丁基、氰基甲基、氰基乙基、氰基正丙基、氰基异丙基、羧基甲基、羧基乙基、羧基正丙基、羧基异丙基、氟甲基、氯甲基、溴甲基、二氟甲基、二氯甲基、三氟甲基、三氯甲基、氟二氯甲基、氯二氟甲基、氟乙基、氯乙基、二氟乙基、二氯乙基、氯氟乙基、三氟乙基、三氯乙基、氟二氯乙基、氯二氟乙基、四氟乙基、氯三氟乙基、二氯二氟乙基、五氟乙基、甲氧基甲基、乙氧基甲基、正或异丙氧基甲基、甲氧基乙基、乙氧基乙基、正或异丙氧基乙基、甲氧基丙基、乙氧基丙基、甲氧基羰基甲基、乙氧基羰基甲基、正或异丙氧基羰基甲基、甲氧基羰基乙基、乙氧基羰基乙基、正或异丙氧基羰基乙基、甲氧基羰基丙基、乙氧基羰基丙基、甲基氨基羰基甲基、乙基氨基羰基甲基、正或异丙基氨基羰基甲基、甲基氨基羰基乙基、乙基氨基羰基乙基、正或异丙基氨基羰基乙基、二甲基氨基羰基甲基、二甲基氨基羰基乙基、乙酰基、丙酰基、正或异丁酰基、三氟乙酰基、氯乙酰基、二氯乙酰基、三氯乙酰基、甲氧基乙酰基、乙氧基乙酰基、甲氧基、乙氧基、正或异丙氧基、氰基甲氧基、氰基乙氧基、氰基正丙氧基、氰基异丙氧基、氟甲氧基、二氟甲氧基、三氟甲氧基、氟二氯甲氧基、氯二氟甲氧基、氟乙氧基、氯乙氧基、二氟乙氧基、二氯乙氧基、氯氟乙氧基、三氟乙氧基、三氯乙氧基、氟二氯乙氧基、氯二氟乙氧基、甲氧基甲氧基、乙氧基甲氧基、正或异丙氧基甲氧基、甲氧基乙氧基、乙氧基乙氧基、正或异丙氧基乙氧基、羧基甲氧基、羧基乙氧基、甲氧基羰基甲氧基、乙氧基羰基甲氧基、正或异丙氧基羰基甲氧基、甲氧基羰基乙氧基、乙氧基羰基乙氧基、正或异丙氧基羰基乙氧基、甲基氨基羰基甲氧基、乙基氨基羰基甲氧基、正或异丙基氨基羰基甲氧基、甲基氨基羰基乙氧基、乙基氨基羰基乙氧基、正或异丙基氨基羰基乙氧基、二甲基氨基羰基甲氧基、二甲基氨基羰基乙氧基、甲氧基羰基、乙氧基羰基、正或异丙氧基羰基、丙烯氧基、丁烯氧基、丙炔氧基、丁炔氧基、甲硫基、乙硫基、正或异丙硫基、二氟甲硫基、三氟甲硫基、氟二氯甲硫基、氯二氟甲硫基、甲基亚磺酰基、乙基亚磺酰基、正或异丙基亚磺酰基、三氟甲基亚磺酰基、甲基磺酰基、乙基磺酰基、正或异丙基磺酰基、三氟甲基磺酰基、(分别任选被氟、氯、甲氧基或乙氧基取代的)乙酰基氨基、丙酰基氨基、正或异丁酰基氨基、甲氧基羰基氨基、乙氧基羰基氨基、正或异丙氧基羰基氨基、(分别任选被氟和/或氯取代的)甲基磺酰基氨基、乙基磺酰基氨基、正或异丙基磺酰基氨基、(分别任选被氟和/或氯取代的)环丙基、环丁基、环戊基、环己基、环丙氧基、环丁氧基、环戊氧基、环己氧基、环丙硫基、环丁硫基、环戊硫基、环己硫基、环丙基氨基、环丁基氨基、环戊基氨基、环己基氨基、环丙基甲基、环丁基甲基、环戊基甲基、环己基甲基、环丙基甲氧基、环丁基甲氧基、环戊基甲氧基、环己基甲氧基、环丙基甲硫基、环丁基甲硫基、环戊基甲硫基、环己基甲硫基、环丙基甲基氨基、环丁基甲基氨基、环戊基甲基氨基、环己基甲基氨基、(分别任选被硝基、氰基、氟、氯、溴、甲基、乙基、正或异丙基、正丁基、异丁基、仲丁基或叔丁基、三氟甲基、甲氧基、乙氧基、正或异丙氧基、二氟甲氧基或三氟甲氧基取代的)苯基、吡啶基、苯氧基、苯硫基、苯基氨基、苄基、苄氧基、苄硫基或苄基氨基,
或代表一个下列基团:
其中用虚线表示的每个键是单键或双键,并且每个杂环优选仅携带任何所需组合的定义R7和/或R8的两个取代基,
Q代表氧或硫,
R7代表氢、羟基、巯基、氰基、氟、氯、溴、碘;代表分别任选被氟、氯、甲氧基、乙氧基、正或异丙氧基、甲硫基、乙硫基、正或异丙硫基、甲基亚磺酰基、乙基亚磺酰基、正或异丙基亚磺酰基、甲基磺酰基、乙基磺酰基、正或异丙基磺酰基取代的下列基团:甲基、乙基、正或异丙基、正丁基、异丁基、仲丁基或叔丁基、甲氧基、乙氧基、正或异丙氧基、正丁氧基、异丁氧基、仲丁氧基或叔丁氧基、甲硫基、乙硫基、正或异丙硫基、正丁硫基、异丁硫基、仲丁硫基或叔丁硫基、甲基亚磺酰基、乙基亚磺酰基、正或异丙基亚磺酰基、甲基磺酰基、乙基磺酰基、正或异丙基磺酰基;代表甲基氨基、乙基氨基、正或异丙基氨基、正丁基氨基、异丁基氨基、仲丁基氨基或叔丁基氨基、二甲基氨基、二乙基氨基、二正丙基氨基或二异丙基氨基;代表分别任选被氟和/或氯取代的乙烯基、丙烯基、丁烯基、乙炔基、丙炔基、丁炔基、丙烯氧基、丁烯氧基、丙烯硫基、丁烯硫基、丙烯基氨基或丁烯基氨基;代表分别任选被氟和/或氯取代的环丙基、环丁基、环戊基、环己基、环丙氧基、环丁氧基、环戊氧基、环己氧基、环丙硫基、环丁硫基、环戊硫基、环己硫基、环丙基氨基、环丁基氨基、环戊基氨基、环己基氨基、环丙基甲基、环丁基甲基、环戊基甲基、环己基甲基、环丙基甲氧基、环丁基甲氧基、环戊基甲氧基、环己基甲氧基、环丙基甲硫基、环丁基甲硫基、环戊基甲硫基、环己基甲硫基、环丙基甲基氨基、环丁基甲基氨基、环戊基甲基氨基或环己基甲基氨基;或代表分别任选被氟、氯、甲基、乙基、正或异丙基、正丁基、异丁基、仲丁基或叔丁基、甲氧基、乙氧基、正或异丙氧基取代的苯基、苯氧基、苯硫基、苯基氨基、苄基、苄氧基、苄硫基或苄基氨基,且
R8代表氢、羟基、氨基;代表分别任选被氟和/或氯、甲氧基或乙氧基取代的甲基、乙基、正或异丙基、正丁基、异丁基或仲丁基、甲氧基、乙氧基、正或异丙氧基、甲基氨基、乙基氨基或二甲基氨基;代表分别任选被氟和/或氯取代的乙烯基、丙烯基、乙炔基、丙炔基或丙烯氧基;代表分别任选被氟和/或氯取代的环丙基、环丁基、环戊基、环己基、环丙基甲基、环丁基甲基、环戊基甲基或环己基甲基;或代表分别任选被氟、氯、甲基、乙基、正或异丙基、正丁基、异丁基、仲丁基或叔丁基、甲氧基、乙氧基、正或异丙氧基取代的苯基或苄基。
R1非常特别优选代表氢、氨基或甲基。
R2非常特别优选代表氰基、羧基、氨基甲酰基、硫代氨基甲酰基;代表分别任选被氟和/或氯取代的甲基或乙基;或代表甲氧基羰基或乙氧基羰基。
R3非常特别优选代表氢、氟、氯、溴;或代表任选被氟和/或氯取代的甲基。
R4非常特别优选代表氢、氟或氯。
R5非常特别优选代表氰基、硫代氨基甲酰基、氯、溴;或代表分别任选被氟和/或氯取代的甲基或甲氧基。
R6非常特别优选代表经由N连接的饱和或不饱和单环或二环含氮杂环基,所述杂环基选自:吡咯基、吡咯烷基、吡唑基、咪唑基、异噁唑烷基、三唑基、哌啶基、吗啉基、硫代吗啉基、哌嗪基,并且所述杂环基可任选被下列基团取代:硝基、羟基、巯基、氨基、氰基、羧基、氨基甲酰基、氟、氯、溴、碘、甲基、乙基、正或异丙基、正丁基、异丁基、仲丁基或叔丁基、氰基甲基、氰基乙基、氰基正丙基、氰基异丙基、羧基甲基、羧基乙基、羧基正丙基、羧基异丙基、氟甲基、氯甲基、溴甲基、二氟甲基、二氯甲基、三氟甲基、三氯甲基、氟二氯甲基、氯二氟甲基、氟乙基、氯乙基、二氟乙基、二氯乙基、氯氟乙基、三氟乙基、三氯乙基、氟二氯乙基、氯二氟乙基、四氟乙基、氯三氟乙基、二氯二氟乙基、五氟乙基、甲氧基甲基、乙氧基甲基、正或异丙氧基甲基、甲氧基乙基、乙氧基乙基、正或异丙氧基乙基、甲氧基丙基、乙氧基丙基、甲氧基羰基甲基、乙氧基羰基甲基、正或异丙氧基羰基甲基、甲氧基羰基乙基、乙氧基羰基乙基、正或异丙氧基羰基乙基、甲氧基羰基丙基、乙氧基羰基丙基、甲基氨基羰基甲基、乙基氨基羰基甲基、正或异丙基氨基羰基甲基、甲基氨基羰基乙基、乙基氨基羰基乙基、正或异丙基氨基羰基乙基、二甲基氨基羰基甲基、二甲基氨基羰基乙基、甲氧基、乙氧基、正或异丙氧基、氰基甲氧基、氰基乙氧基、氰基正丙氧基、氰基异丙氧基、氟甲氧基、二氟甲氧基、三氟甲氧基、氟二氯甲氧基、氯二氟甲氧基、氟乙氧基、氯乙氧基、二氟乙氧基、二氯乙氧基、氯氟乙氧基、三氟乙氧基、三氯乙氧基、氟二氯乙氧基、氯二氟乙氧基、甲氧基甲氧基、乙氧基甲氧基、正或异丙氧基甲氧基、甲氧基乙氧基、乙氧基乙氧基、正或异丙氧基乙氧基、羧基甲氧基、羧基乙氧基、甲氧基羰基甲氧基、乙氧基羰基甲氧基、正或异丙氧基羰基甲氧基、甲氧基羰基乙氧基、乙氧基羰基乙氧基、正或异丙氧基羰基乙氧基、甲基氨基羰基甲氧基、乙基氨基羰基甲氧基、正或异丙基氨基羰基甲氧基、甲基氨基羰基乙氧基、乙基氨基羰基乙氧基、正或异丙基氨基羰基乙氧基、二甲基氨基羰基甲氧基、二甲基氨基羰基乙氧基、甲氧基羰基、乙氧基羰基、正或异丙氧基羰基、丙烯氧基、丁烯氧基、丙炔氧基、丁炔氧基、甲硫基、乙硫基、正或异丙硫基、二氟甲硫基、三氟甲硫基、氟二氯甲硫基、氯二氟甲硫基、甲基亚磺酰基、乙基亚磺酰基、正或异丙基亚磺酰基、三氟甲基亚磺酰基、甲基磺酰基、乙基磺酰基、正或异丙基磺酰基、三氟甲基磺酰基、(分别任选被氟、氯、甲氧基或乙氧基取代的)乙酰基氨基、丙酰基氨基、正或异丁酰基氨基、甲氧基羰基氨基、乙氧基羰基氨基、正或异丙氧基羰基氨基、(分别任选被氟和/或氯取代的)甲基磺酰基氨基、乙基磺酰基氨基、正或异丙基磺酰基氨基、(分别任选被氟和/或氯取代的)环丙基、环丁基、环戊基、环己基、环丙氧基、环丁氧基、环戊氧基、环己氧基、环丙硫基、环丁硫基、环戊硫基、环己硫基、环丙基氨基、环丁基氨基、环戊基氨基、环己基氨基、环丙基甲基、环丁基甲基、环戊基甲基、环己基甲基、环丙基甲氧基、环丁基甲氧基、环戊基甲氧基、环己基甲氧基、环丙基甲硫基、环丁基甲硫基、环戊基甲硫基、环己基甲硫基、环丙基甲基氨基、环丁基甲基氨基、环戊基甲基氨基、环己基甲基氨基、(分别任选被硝基、氰基、氟、氯、溴、甲基、乙基、正或异丙基、正丁基、异丁基、仲丁基或叔丁基、三氟甲基、甲氧基、乙氧基、正或异丙氧基、二氟甲氧基或三氟甲氧基取代的)苯基、吡啶基、苯氧基、苯硫基、苯基氨基、苄基、苄氧基、苄硫基或苄基氨基,
其中用虚线表示的每个键是单键或双键,并且每个杂环优选仅携带任何所需组合的定义R7和/或R8的两个取代基,
Q优选代表氧,
R7优选代表氢、羟基、巯基、氰基、氟、氯;代表分别任选被氟、氯、甲氧基、乙氧基、甲硫基或乙硫基取代的甲基或乙基、甲氧基、乙氧基或甲硫基;代表甲基氨基、乙基氨基、二甲基氨基或二乙基氨基;代表分别任选被氟和/或氯取代的环丙基、环丁基、环戊基、环己基、环丙氧基、环丁氧基、环戊氧基或环己氧基;或代表分别任选被氟、氯、甲基、乙基、甲氧基或乙氧基取代的苯基、苯氧基、苄基或苄氧基。
R8优选代表氢、羟基、氨基;代表分别任选被氟和/或氯、甲氧基或乙氧基取代的甲基或乙基、甲氧基、乙氧基、甲基氨基、乙基氨基或二甲基氨基;代表分别任选被氟和/或氯取代的环丙基、环丁基、环戊基、环己基、环丙基甲基、环丁基甲基、环戊基甲基或环己基甲基;或代表分别任选被氟、氯、甲基、乙基、甲氧基或乙氧基取代的苯基或苄基。
R2最优选代表分别任选被氟和/或氯取代的甲基、乙基;或代表甲氧基羰基或乙氧基羰基。
R3最优选代表氢、氟、氯;或代表任选被氟和/或氯取代的甲基。
R5最优选代表氰基、氯或溴。
R6最优选代表经由N连接的杂环基,所述杂环基选自:吡咯烷基、异噁唑烷基、哌啶基、吗啉基、硫代吗啉基、哌嗪基,并且所述杂环基可任选被下列基团取代:羟基、氨基、氟、氯、甲基、乙基、三氟甲基、甲硫基、乙硫基、甲基氨基、二甲基氨基、二乙基氨基、环丙基、环丁基、环戊基或环己基;
或代表一个下列基团R6特别优选代表下式所示基团
本发明还优选提供了式(I)化合物的钠盐、钾盐、镁盐、钙盐、铵盐、C1-C4-烷基铵盐、二-(C1-C4-烷基)-铵盐、三-(C1-C4-烷基)-铵盐、四-(C1-C4-烷基)-铵盐、三-(C1-C4-烷基)-锍盐、C5-或C6-环烷基-铵盐和二-(C1-C2-烷基)-苄基-铵盐,其中A1、A2、R1、R2、R3、R4、R5和R6分别如上所定义,或这些化合物与金属例如铜、铁、钴、镍的络合化合物(配位化合物)。
依据本发明,包含上述优选含义的组合的式(I)化合物是优选的。
依据本发明,包含上述特别优选含义的组合的式(I)化合物是特别优选的。
依据本发明,包含上述非常特别优选含义的组合的式(I)化合物是非常特别优选的。
依据本发明,包含上述最优选含义的组合的式(I)化合物是最优选的。
上述一般或优选的基团定义既适用于式(I)终产物,也相应地适用于在各种情况下其制备所需的原料或中间体。这些基团定义可按照需要彼此组合,即包括给定优选范围之间的组合。
定义如下的式(I)化合物是非常特别优选的一组化合物:其中
R1代表氢、氨基或甲基,
R2代表氰基或三氟甲基,
R3代表氢、氟、氯或甲基,
R4代表氢、氟或氯,
R5代表氰基、硫代氨基甲酰基、氯或溴,
Q代表氧,
R7代表氢、氯、溴、碘;代表分别任选被氟、氯、甲氧基、乙氧基、甲硫基、乙硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基或乙基磺酰基取代的甲基、乙基、正或异丙基、甲氧基、乙氧基、正或异丙氧基、甲硫基、乙硫基、正或异丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基、乙基磺酰基;代表甲基氨基、乙基氨基、正或异丙基氨基、二甲基氨基或二乙基氨基;代表分别任选被氟和/或氯取代的乙烯基、丙烯基、乙炔基、丙炔基、丙烯氧基、丙烯硫基或丙烯基氨基;代表任选被氟和/或氯取代的环丙基;或代表分别任选被氟、氯、甲基、乙基、甲氧基或乙氧基取代的苯基、苯氧基、苯硫基、苯基氨基、苄基、苄氧基、苄硫基或苄基氨基,且
R8代表氢、氨基;代表分别任选被氟和/或氯、甲氧基或乙氧基取代的甲基、乙基、正或异丙基、甲氧基、乙氧基、正或异丙氧基;代表任选被氟和/或氯取代的环丙基;或代表分别任选被氟、氯、甲基、乙基、甲氧基或乙氧基取代的苯基或苄基。
本发明新的通式(I)取代的苯基尿嘧啶类化合物具有令人感兴趣的生物性质。特别是,它们具有强的除草活性。
本发明新的通式(I)取代的苯基尿嘧啶类化合物是这样制得的:将通式(II)卤代甲基苯基尿嘧啶化合物
其中
R1、R2、R3、R4和R5分别如上所定义,且
X代表卤素,
与通式(III)氮杂环化合物反应
H-R6 (III)
其中
R6如上所定义,
任选在一种或多种反应辅助剂存在下,以及任选在一种或多种稀释剂存在下进行该反应,
并且任选,随后以常规方式-一般是通过亲电或亲核取代反应或氧化或还原反应或加成反应-将所得通式(I)化合物转化成在取代基定义范围内的其它通式(I)化合物。
可通过常规方法将通式(I)化合物转化成依据上述定义的其它通式(I)化合物,例如通过胺化或烷基化(例如R1:H→NH2,H→CH3)、与二氰或硫化氢反应(例如R5:Br→CN,CN→CSNH2,参见制备实施例)。
在本发明方法用于制备通式(I)化合物作为原料使用的卤代甲基-苯基尿嘧啶类化合物是通过式(II)一般性定义的。在通式(II)中,R1、R2、R3、R4和R5分别优选或特别具有在上文中描述本发明通式(I)化合物时所提及的关于R1、R2、R3、R4、R5和R6的优选、特别优选、非常特别优选或最优选的含义;X优选代表氟、氯、溴或碘,特别是氯或溴。
通式(II)原料化合物迄今为止没有在文献中公开过,它们作为新的物质也形成了本发明主题的一部分。
其中
R1、R2、R3、R4和R5分别如上所定义,
与卤化剂例如N-溴-琥珀酰亚胺或N-氯-琥珀酰亚胺在反应辅助剂例如2,2′-偶氮-二-(2-甲基-丙腈)-还命名为2,2′-偶氮异丁腈存在下,以及在稀释剂例如四氯化碳存在下于50℃-100℃的温度下反应(参见制备实施例)。
需要用作前体的通式(IV)甲基苯基尿嘧啶化合物迄今为止没有在文献中公开过,它们作为新的物质也形成了本发明主题的一部分。
新的通式(IV)甲基苯基尿嘧啶化合物是这样获得的:将通式(V)氨基链烯酸酯化合物
其中
R1、R2和R3分别如上所定义,且
R代表烷基、芳基或芳基烷基(优选为C1-C4-烷基、苯基或苄基,特别是甲基或乙基),
其中
R4和R5分别如上所定义,
或者与通式(VII)甲基苯基尿烷化合物(甲基苯基氨基甲酸酯化合物)于0℃-150℃温度下反应
其中
R4和R5分别如上所定义,且
R代表烷基、芳基或芳基烷基(优选为C1-C4-烷基、苯基或苄基,特别是甲基或乙基),
任选在反应辅助剂例如氢化钠存在下,以及任选在稀释剂例如N,N-二甲基甲酰胺存在下在0~150℃温度下进行该反应,
并且任选,随后可以以常规方式-一般是通过亲电或亲核取代反应-将所得通式(IV)化合物转化成在取代基定义范围内的其它通式(IV)化合物。
可通过常规方法将通式(IV)化合物转化成依据上述定义的其它通式(IV)化合物,例如通过胺化或烷基化(例如R1:H→NH2,H→CH3)、与二氰或硫化氢反应(例如R5:Br→CN,CN→CSNH2,参见制备实施例)。
需要用作前体的通式(V)氨基链烯酸酯是已知的和/或可通过自身已知的方法制得(参见J.Heterocycl.Chem.9(1972),513-522)。
除了化合物异氰酸3-甲基-4-溴-苯酯(参见GB-A-1503244)和化合物N-(4-溴-3-甲基-苯基)-氨基甲酸O-甲基酯和O-乙基酯(例如WO-A-96/19477)以外,需要用作前体的通式(VI)异氰酸甲基苯酯化合物或通式(VII)甲基苯基尿烷化合物迄今为止没有在文献中公开过,并且除了上述具体提及的化合物异氰酸4-溴-3-甲基-苯酯、N-(4-溴-3-甲基-苯基)-氨基甲酸O-甲基酯和O-乙基酯)以外,它们也可以作为新的物质形成本发明主题的一部分。特别优选的新化合物是异氰酸4-溴-2-氟-5-甲基-苯酯,异氰酸4-氰基-2-氟-5-甲基-苯酯,N-(4-溴-2-氟-5-甲基-苯基)-氨基甲酸O-甲基酯和O-乙基酯,和N-(4-氰基-2-氟-5-甲基-苯基)-氨基甲酸O-甲基酯和O-乙基酯。
其中
R4和R5分别如上所定义,
与光气在稀释剂例如氯苯存在下于-20℃-+150℃温度下反应(还参见EP-A-648749)。
其中
R4和R5分别如上所定义,
与通式(IX)氯羰基化合物于-20℃-+100℃温度下反应
RO-CO-Cl (IX)
其中
R如上所定义,
任选在酸性接受体例如吡啶存在下,以及任选在稀释剂例如二氯甲烷存在下进行该反应(参见制备实施例)。
除了化合物4-氨基-2-甲基-苄腈(参见US-A-4 191 775)和4-溴-3-甲基-苯胺(参见WO-A-98/50358)以外,需要用作前体的通式(VIII)甲苯胺衍生物迄今为止没有在文献中公开过,并且除了化合物4-氨基-2-甲基苄腈和4-溴-3-甲基-苯胺以外,它们作为新的物质也形成了本发明的一部分。特别优选的新化合物是4-溴-2-氟-5-甲基-苯胺和4-氰基-2-氟-5-甲基-苯胺(也命名为4-氨基-5-氟-2-甲基-苄腈)。
其中
R4如上所定义,
与溴化剂例如苄基三甲基三溴化铵于0℃-100℃温度下反应,任选在反应辅助剂例如碳酸钙存在下,任选在一种或多种稀释剂例如二氯甲烷和甲醇存在下进行该反应(参见制备实施例),并且任选,在120℃-180℃温度下用氰化剂例如氰化铜(I)处理所得4-溴-3-甲基-苯胺衍生物,任选在稀释剂例如N,N-二甲基甲酰胺存在下进行该反应。
式(III)提供了在制备通式(I)化合物的本发明方法中用作原料的氮杂环化合物的一般定义。在通式(III)中,R6优选具有在上文中描述本发明式(I)化合物时所提及的关于R6的优选、特别优选、非常特别优选或最优选的含义。
式(IX)和(X)化合物是已知的有机化学物质。在通式(X)中,R4优选具有在上文中描述本发明式(I)化合物时所提及的关于R4的优选、特别优选、非常特别优选或最优选的含义。
通式(III)原料是已知的有机化学物质。
优选使用一种或多种反应辅助剂来进行制备通式(I)化合物的本发明方法。适用于本发明方法的反应辅助剂一般是常规无机或有机碱或酸性接受体。它们优选包括碱金属或碱土金属乙酸盐、氨基化物、碳酸盐、碳酸氢盐、氢化物、氢氧化物或醇化物,例如乙酸钠、乙酸钾或乙酸钙,氨基锂、氨基钠、氨基钾或氨基钙,碳酸钠、碳酸钾或碳酸钙,碳酸氢钠、碳酸氢钾或碳酸氢钙,氢化锂、氢化钠、氢化钾或氢化钙,氢氧化锂、氢氧化钠、氢氧化钾或氢氧化钙,甲醇钠、乙醇钠、正丙醇钠、异丙醇钠、正丁醇钠、异丁醇钠、仲丁醇钠或叔丁醇钠,甲醇钾、乙醇钾、正丙醇钾、异丙醇钾、正丁醇钾、异丁醇钾、仲丁醇钾或叔丁醇钾;此外还有碱性有机氮化合物,例如三甲胺、三乙胺、三丙基胺、三丁基胺、乙基二异丙基胺、N,N-二甲基环己基胺、二环己基胺、乙基二环己基胺、N,N-二甲基苯胺、N,N-二甲基苄基胺、吡啶、2-甲基吡啶、3-甲基吡啶、4-甲基吡啶、2,4-二甲基吡啶、2,6-二甲基吡啶、3,4-二甲基吡啶和3,5-二甲基吡啶、5-乙基-2-甲基吡啶、4-二甲基氨基吡啶、N-甲基哌啶、1,4-二氮杂二环[2,2,2]辛烷(DABCO)、1,5-二氮杂二环[4,3,0]壬-5-烯(DBN)、或1,8-二氮杂二环[5,4,0]十一碳-7-烯(DBU)。
适用于本发明方法的其它合适的反应辅助剂是相转移催化剂。可提及的这样的催化剂的实例有:
四丁基溴化铵、四丁基氯化铵、四辛基氯化铵、四丁基硫酸氢铵、甲基三辛基氯化铵、十六烷基三甲基氯化铵、十六烷基三甲基溴化铵、苄基三甲基氯化铵、苄基三乙基氯化铵、苄基三甲基氢氧化铵、苄基三乙基氢氧化铵、苄基三丁基氯化铵、苄基三丁基溴化铵、四丁基溴化鏻、四丁基氯化鏻、三丁基十六烷基溴化鏻、丁基三苯基氯化鏻、乙基三辛基溴化鏻、四苯基溴化鏻。
制备通式(I)化合物的本发明方法优选使用一种或多种稀释剂来进行。除了水以外,适于进行本发明方法的稀释剂尤其是惰性有机溶剂。它们特别包括脂族、脂环族或芳族任选卤代的烃,例如汽油、苯、甲苯、二甲苯、氯苯、二氯苯、石油醚、己烷、环己烷、二氯甲烷、氯仿、四氯化碳;醚,例如乙醚、二异丙基醚、二氧杂环己烷、四氢呋喃或乙二醇二甲醚或乙二醇二乙醚;酮,例如丙酮、丁酮或甲基异丁基酮;腈,例如乙腈、丙腈或丁腈;酰胺,例如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基甲酰胺、N-甲基吡咯烷酮、或六甲基磷酰三胺;酯,例如乙酸甲酯或乙酸乙酯;亚砜,例如二甲亚砜;醇,例如甲醇、乙醇、正丙醇或异丙醇、乙二醇一甲醚、乙二醇一乙醚、二甘醇一甲醚、二甘醇一乙醚,它们与水或纯化水的混合物。
当进行本发明方法时,反应温度可以在较宽的范围内变化。本发明方法一般在0℃-150℃、优选10℃-120℃温度下进行。
本发明方法一般在常压下进行。然而,也可以在高压或减压条件下-一般是0.1巴-10巴压力下进行本发明方法。
为了进行本发明方法,原料一般以大约等摩尔量使用。然而,也可以以较大过量使用一种成分。反应一般在合适的稀释剂中在反应辅助剂存在下进行,并且一般将反应混合物在所需温度搅拌数小时。通过常规方法进行后处理(参见制备实施例)。
本发明活性化合物可用作脱叶剂、干燥剂、稻草杀死剂、和尤其是除草剂。所谓杂草,从最广义上来讲,应理解为在不需要它们的地方生长的所有植物。本发明化合物是起广谱除草剂的作用还是起选择性除草剂的作用基本上取决于其用量。
本发明活性化合物可用于杀灭例如下述植物:
以下各属的双子叶杂草:苘麻属、苋属、豕草属、Anoda、春黄菊属、Aphanes、滨藜属、雏菊属、鬼针草属、荠属、飞廉属、决明属、矢车菊属、藜属、蓟属、旋花属、曼陀罗属、金钱草属、刺酸模属、糖芥属、大戟属、鼬瓣花属、牛膝菊属、猪殃殃属、木槿属、番薯属、地肤属、夜芝麻属、独行菜属、母草属、母菊属、薄荷属、山靛属、羊鱼属(Mullugo)、勿忘草属、罂粟属、牵牛属、车前属、蓼属、马齿苋属、毛茛属、萝卜属、焊菜属、水松叶属、酸模属、猪毛菜属、千里光属、田菁属、黄花稔属、芸苔属、茄属、苦苣菜属、尖瓣花属、繁缕属、蒲公英属、遏蓝菜属、三叶草属、荨麻属、婆婆纳属、堇菜属、苍耳属。
以下各属的双子叶农作物:落花生属、甜菜属、芥属、黄瓜属、南瓜属、向日葵属、胡萝卜属、大豆属、棉属、番薯属、莴苣属、亚麻属、番茄属、烟草属、菜豆属、豌豆属、茄属、野豌豆属。
以下各属的单子叶杂草:山羊草属、冰草属、翦股颖属、看麦娘属、Apera、燕麦属、臂形草属、雀麦属、蒺藜草属、鸭跖草属、狗牙根属、莎草属、龙爪茅属、马唐属、稗属、荸荠属、蟀蟋草属、画眉草属、野黍属、羊茅属、飘拂草属、异蕊花属、白矛属、鸭嘴草属、千斤子属、毒麦属、雨久花属、黍属、雀稗属、鹃草属、梯牧草属、早熟禾属、筒轴茅属、慈菇属、厂草属、狗尾草属、蜀黍属。
以下各属的单子叶农作物:葱属、菠罗属、天门冬属、燕麦属、大麦属、稻属、黍属、甘蔗属、黑麦属、高梁属、黑小麦属、小麦属、玉蜀黍属。
然而,本发明活性化合物的应用决不限于这些属的植物,还可以以相同方式延伸到其它植物。
根据浓度,本发明活性化合物适于控制例如工业场地和铁路轨道,以及有和没有树木生长的道路和场院的所有杂草。同样,本发明活性化合物可用于控制多年生农作物例如森林、观赏林、果园、葡萄园、柑桔园、坚果园、香蕉林、咖啡园、茶叶种植园、橡胶种植园、油棕榈种植园、可可种植园、浆果种植园和蛇麻草田中的杂草,以及控制草坪和草地以及牧场中的杂草,和用于选择性地控制一年生长农作物中的杂草。
当用于土壤和上述植物地上部分时,本发明式(I)活性化合物具有强的除草活性和广的活性作用谱。在一定程度上,它们还适于在单子叶农作物和双子叶农作物中通过芽前和芽后法选择性地控制单子叶和双子叶农作物。
本发明活性化合物还可以以一定浓度或施用比例用于控制动物害虫和真菌或细菌植物疾病。任选,本发明活性化合物还可以用作合成其它活性化合物的中间体或前体。
本发明化合物可用于处理所有植物和植物的部分。在本文中,应当理解植物是指所有植物和植物群体,例如需要和不需要的野生植物或农作物(包括天然存在的农作物)。农作物可以是可通过下述方法获得的植物:常规繁殖法和优化方法,或生物技术和基因工程法,或这些方法的组合,包括转基因植物,和可以或不可以受植物繁殖证书保护的植物品种。应当理解,植物部分是指所有上述植物的土壤下面和土壤上面的部分以及植物器官,例如芽、叶、花和根,可提及的实例有叶、针叶、茎、树干、花、果实体、果实、种子、根、块茎和根茎。植物部分还包括收割的植物以及生长性和生殖性繁殖材料,例如秧苗、决茎、根茎、切块和种子。
用本发明活性化合物处理植物和植物部分可直接进行,或通过依据常规处理法作用于其环境、习生地或贮藏区域来进行,例如通过浸泡、喷雾、蒸发、雾化、洒、刷来施加活性化合物,对于繁殖材料、特别是对于种子,通过单层或多层包衣来施加活性化合物。
可将本发明活性化合物转化成常规制剂,例如溶液、乳剂、可润湿粉剂、悬浮剂、粉剂、撒粉剂、糊剂、可溶性粉剂、粒剂、悬浮剂-乳剂浓缩物、浸渗着活性化合物的天然和合成物质、和在聚合物中的微胶囊。
这些制剂可通过已知方法制得,例如通过将活性化合物与增容剂即液体溶剂和/或固体载体混合,并任选使用表面活性剂,即乳化剂和/或分散剂和/或泡沫形成剂来制得。
如果所用的增容剂是水,还可以使用有机溶剂作为辅助溶剂。大抵合适的液体溶剂有:芳族溶剂例如二甲苯、甲苯或烷基萘,氯代芳族烃和氯代脂族烃例如氯苯、氯乙烯或二氯甲烷,脂族烃例如环己烷或石蜡如石油馏分,矿物油和植物油,醇例如丁醇或二醇,及其醚和酯,酮例如丙酮、甲基乙基酮、甲基异丁基酮或环己酮,强极性溶剂例如二甲基甲酰胺和二甲亚砜,和水。
合适的固体载体有:例如铵盐和土地天然矿物,例如高岭土、粘土、滑石、白垩、石英、绿坡缕石、蒙脱石或硅藻土,和土地合成矿物例如高度分散的二氧化硅、矾土和硅酸盐;适用于粒剂的固体载体有:例如粉碎或分馏的天然岩石,例如方解石、大理石、浮石、海泡石和白云石,和合成的无机和有机粗粉颗粒以及有机物质的颗粒例如锯屑、椰壳、玉米棒碎块和烟草茎;合适的乳化剂和/或泡沫形成剂有:例如非离子和阴离子乳化剂,例如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇例如烷基芳基聚二醇醚、烷基磺酸盐、烷基硫酸盐、芳基磺酸盐和蛋白水解产物;合适的分散剂有:例如木素亚硫酸盐废液和甲基纤维素。
可在制剂中使用增粘剂例如羧甲基纤维素、天然及合成粉末、颗粒或胶乳形式的聚合物例如阿拉伯胶、聚乙烯醇和聚乙酸乙烯酯,以及天然磷脂例如脑磷脂和卵磷脂,与合成磷脂。其它合适的添加剂是矿物油和植物油。
还可以使用染料,例如无机色素如氧化铁、氧化钛、普鲁士蓝,和有机染料例如茜素染料、偶氮染料和金属酞菁染料,和微量营养素例如铁、锰、硼、铜、钴、钼和锌的盐。
制剂一般含有0.1-95%重量的活性化合物、优选0.5-90%重量的活性化合物。
为了控制杂草,本发明活性化合物(自身或在其制剂中)可以作为与已知除草剂和/或改善农作物相容性的物质(“安全剂”)的混合物使用,其中成品制剂或罐装混合物都是可行的。与包含一种或多种已知除草剂和安全剂的杂草杀灭剂的混合物也是可行的。
所述混合物的可能组分是已知的除草剂,例如:
乙草胺、三氟羧草醚、苯草醚、甲草胺、禾草灭、莠灭净、Amicarbazone、先甲草胺、酰嘧磺隆、莎稗磷、磺草灵、莠去津、唑啶炔草、四唑嘧磺隆、Beflubutamid、草除灵、呋草黄、苄嘧磺隆、苯达松、Benzfendizone、Benzobicyclon、吡草酮、新燕灵、双丙胺膦、治草醚、双草醚、溴丁酰草胺、溴酚肟、溴草腈、丁草胺、Butafenacil(-allyl)、丁氧环酮、苏达灭、苯酮唑、醌肟草、双酰草胺、氟酮唑草、甲氧除草醚、豆科畏、氯草敏、氯嘧磺隆、草枯醚、绿黄隆、绿麦隆、Cinidon(-ethyl)、环庚草醚、醚磺隆、Clefoxydim、烯草酮、炔草酸、异恶草松、氯甲酰草胺、二氯吡啶酸、Clopyrasulfuron(-methyl)、唑嘧磺胺盐、Cumyluron、氰乙酰肼、Cybutryne、草减特、环丙嘧磺隆、噻草酮、氰氟草酯、2,4-D、2,4-DB、甜菜安、燕麦敌、麦草畏、高2,4-滴丙酸、禾草灵、唑嘧磺胺、乙酰甲草胺、野燕枯、吡氟酰草胺、二氟吡隆、唑隆、哌草丹、二甲草胺、异戊净、二甲吩草胺、Dimexyflam、敌乐氨、草乃敌、杀草快、氟硫草定、敌草隆、香草隆、Epropodan、EPTC、戊草丹、乙丁烯氟灵、胺苯磺隆、唑啶草、Ethoxyfen、乙氧嘧黄隆、乙苯酰草、精恶唑禾草灵、Fentrazamide、麦草氟异丙酯、麦草氟异丙酯、麦草氟甲酯、啶嘧磺隆、Florasulam、精吡氟禾草灵、Fluazolate、Flucarbazone(-sodium)、Flufenacet、唑嘧磺草胺、氟烯草酸、丙炔氟草胺、Flumipropyn、唑嘧磺草胺、伏草隆、氟咯草酮、乙羧氟草醚、氟胺草唑、Flupropacil、Flurpyrsulfuron(-methyl、-sodium)、芴丁酯、氟啶草酮、氟草酸丁氧异丙酯和氟氯胺啶、氟嘧醇、呋草酮、达草氟、噻唑草酰胺、氟磺胺草醚、Foramsulfuron、草铵膦、草甘膦(-异丙基铵)、氟硝磺酰胺、氟吡乙禾灵、氟吡甲禾灵、环嗪酮、咪草酸、Imazamethapyr、咪草啶酸、Imazapic、咪唑烟酸、灭草喹、咪唑乙烟酸、唑吡嘧磺隆、Iodosulfuron(-methyl、-sodium)、碘苯腈、异丙乐灵、异丙隆、异恶隆、异恶酰草胺、Isoxachlortole、异恶氟草、异恶草醚、乳氟禾草灵、环草定、利农伦、MCPA、甲氯丙酸、苯噻酰草胺、Mesotrione、苯嗪草酮、吡唑草胺、唑隆、吡喃隆、秀谷隆、(α-)甲氧毒草安、磺草唑胺、甲氧隆、草克净、甲磺隆、禾草特、绿谷隆、萘丙胺、草萘胺、草不隆、烟嘧磺隆、达草减、坪草丹、氨磺乐灵、炔丙恶唑草、恶草酮、环丙氧黄隆、氯恶嗪草、氧氟吩、对草快、壬酸、喷达曼萨林、Pendralin、戊恶唑草、苯敌草、Picolinafen、哌草磷、丙草胺、氟嘧磺隆、Profluazol、扑草净、毒草安、敌稗、恶草酸、异丙草胺、Propoxcarbazone(-sodium)、炔苯酰草胺、苄草丹、氟磺隆、氟唑草酯、Pyrazogyl、吡唑特、吡嘧磺隆、苄草唑、嘧苯草肟、稗草丹、哒草特、Pyridatol、Pyriftalid、肟啶草、嘧草硫醚、二氯喹啉酸、氯甲喹啉酸、灭藻醌、精喹禾灵、喹禾糠酯、砜嘧磺隆、稀禾定、西玛津、西草净、磺草酮、甲磺草胺、甲嘧磺隆、草甘磷、乙黄黄隆、牧草胺、丁噻隆、醌肟草(Tepraloxydim)、特丁津、去草净、噻吩草胺、Thiafluamide、噻唑烟酸、噻二唑胺、噻吩磺隆、禾草丹、仲草丹、三甲苯草酮、野麦威、醚苯磺隆、苯磺隆、定草酯、灭草环、氟乐灵、Trifloxysulfuron、氟胺黄隆、Tritosulfuron。
其它适于混合物的是已知的安全剂,例如
AD-67、BAS-145138、解草酮、喹氧乙酸、抑害腈、2,4-D、DKA-24、抑害胺、香草隆、解草唑、解草安、肟草安、解草呋、Furilazole、Isoxadifen(-ethyl)、MCPA、高2甲4氯丙酸盐、吡咯二酸二乙酯、MG-191、解草腈、PPG-1292、R-29148。
与其它已知活性化合物例如杀真菌剂、杀虫剂、杀螨剂、杀线虫剂、驱鸟剂、植物营养素、和改善土壤结构的活性剂的混合物也是可行的。
活性化合物可以以自身的形式使用、在其制剂中使用,或者在通过进一步稀释由其制得的使用剂型例如即用溶液、悬浮剂、乳剂、粉剂、糊剂和粒剂中使用。它们可通过常规方式例如通过灌溉、喷雾、雾化、或散射来使用。
本发明活性化合物可在植物发芽之前和之后施用。可在播种前将本发明活性化合物掺入到土壤中。
活性化合物的用量可在较宽的范围内变化。其用量基本上取决于所需效果的性质。其用量一般为1g-10kg活性化合物/公顷土壤面积、优选为5g-5kg/公顷。
如上所述,可依据本发明处理所有植物及其部分。在优选的实施方案中,处理野生植物种类和植物品种,或通过常规生物育种例如交叉或原型融合获得的植物及其部分。在另一优选的实施方案中,处理通过基因工程(如果适当的话与常规方法合用)获得的转基因植物和植物品种(基因改性生物体)及其部分。术语“部分”或“植物部分”已在上文中解释过。
特别优选地,依据本发明处理分别商购获得的或正在使用着的植物品种的作物。植物品种应理解为表示具有一些特征(“特性”),并且已通过常规育种、通过诱变或通过重组DNA技术获得的植物。它们可以是品种、生物属型或基因型。
根据植物种类或植物品种、它们的位置和生长条件(土壤、气候、生长周期、施加的营养),依据本发明进行的处理也可产生超叠加(“协同”)作用。因此,例如可降低施用比例和/或扩大活性谱和/或提高依据本发明使用的物质和组合物(还与其它农业化学活性化合物联合使用)的活性,更好的植物生长,提高对高温或低温的耐受,提高对干旱或水或土壤盐内容物的耐受,提高开花能力,更易于收割,加快成熟,更高的收获量,更好的质量和/或更高的收获产品营养值,更好的储藏稳定性和/或收获产品的可加工性,超过实际所预期的作用。
优选依据本发明处理的转基因植物或植物品种(即通过基因工程获得的那些)包括通过基因修饰接受赋予这些植物特别有用的特征(“特性”)的基因物质的所有植物。这样的特征的实例有更好的植物生长,提高对高温或低温的耐受,提高对干旱或水或土壤盐内容物的耐受,提高开花能力,更易于收割,加快成熟,更高的收获量,更好的质量和/或更高的收获产品营养值,更好的储藏稳定性和/或收获产品的可加工性。另外以及特别需要强调的这样的特征的实例有,更好的抗动物和微生物害虫例如昆虫、螨、致植物病的真菌、细菌和/或病毒的植物防护作用,以及提高植物对一些除草活性化合物的耐受力。可提及的转基因植物的实例是重要的农作物例如谷类植物(小麦、稻米)、玉米、大豆、马铃薯、棉花、油菜、以及果实植物(果实是苹果、梨、柑橘果实和葡萄),特别需要强调的是玉米、大豆、马铃薯、棉花和油菜。需要强调的特性尤其是提高通过在植物中形成的毒素来抗昆虫的植物防护作用,所述毒素特别是在植物中通过基因物质由苏云金芽孢杆菌形成的那些(例如通过基因CryIA(a)、CryIA(b)、CryIA(c)、CryIIA、CryIIIA、CryIIIB2、Cry9c、Cry2Ab、Cry3Bb和CryIF和它们的组合)(在下文中称为“Bt植物”)。还特别需要强调的特性是提高通过系统获得抗性(SAR)、系统素、植物抗毒素、elicitor和抗性基因以及相应表达的蛋白和毒素来抗真菌、细菌和毒素的植物防护作用。还特别需要强调的特性是提高植物对一些除草活性化合物例如咪唑啉酮类、磺酰脲类、草甘膦或phosphinotricin的耐受力(例如“PAT”基因)。赋予所需特性的基因也可以彼此组合存在于转基因植物中。可提及的“Bt植物”的实例有以下列商品名销售的玉米变种、棉花变种、大豆变种和马铃薯变种:YIELD GARD(例如玉米、棉花、大豆)、KnockOut(例如玉米)、StarLink(例如玉米)、Bollgard(棉花)、Nucotn(棉花)和NewLeaf(马铃薯)。可提及的耐受除草剂的植物的实例有以下列商品名销售的玉米变种、棉花变种和大豆变种:Roundup Ready(耐受草甘膦,例如玉米、棉花、大豆)、LibertyLink(耐受phosphinotricin,例如油菜)、IMI(耐受咪唑啉酮类)和STS(耐受磺酰脲类,例如玉米)。可提及的耐受除草剂的植物(对于除草剂耐受以常规方法育种的植物)包括以商品名Clearfield销售的变种(例如玉米)。当然,这些叙述也适用于具有这些基因特性或有待开发的基因特性的植物变种,这样的植物将在将来开发出来和/或销售。
可依据本发明用通式(I)化合物或本发明活性化合物的组合以特别有利的方式处理所列出的植物,这样除了良好地控制了杂草以外,还与植物品种的转基因植物产生了上述协同作用。上述关于活性化合物或混合物的优选范围也适用于这些植物的处理。特别需要强调的是,使用在本文中具体提及的化合物或混合物处理植物。
下述实施例举例说明了本发明活性化合物的制备和应用:
制备实施例
实施例1
将1.20g(1.63mMol)2-溴甲基-5-氟-4-(3-甲基-2,6-二氧代-4-三氟甲基-3,6-二氢-1(2H)-嘧啶基)-苄腈、0.15g(1.54mMol)4-甲基-2,4-二氢-3H-1,2,4-三唑-3-酮、0.45g(3.25mMol)碳酸钾和50ml乙腈的混合物加热至沸,回流18小时。然后使用旋转蒸发仪将该混合物减压浓缩,将残余物置于1N盐酸中,并用乙酸乙酯萃取。用硫酸钠将有机相干燥,过滤。将滤液减压浓缩,通过硅胶柱色谱纯化残余物,1.使用二氯甲烷的级分,2.使用乙酸乙酯的级分,3.使用甲醇的级分,通过浓缩从级分3中分离出产物。
获得了0.32g(理论的46%)5-氟-4-(3-甲基-2,6-二氧代-4-三氟甲基-3,6-二氢-1(2H)-嘧啶基)-2-[(4-甲基-5-氧代-4,5-二氢-1H-1,2,4-三唑-1-基)-甲基]-苄腈。
1H-NMR(DMSO-D6,δ):6.57ppm。
在表1中给出的logP值是依据EEC-Directive 79/831 AnnexV.A8通过HPLC(高效液相色谱法)使用反相柱(C18)测定的。温度:43℃。
(a)在酸性范围用于测定的流动相:0.1%磷酸水溶液,乙腈;10%乙腈-90%乙腈的线性梯度-相应的测定结果用a)标记在表1中。
(b)在中性范围用于测定的流动相:0.01M磷酸盐缓冲水溶液,乙腈;10%乙腈-90%乙腈的线性梯度-相应的测定结果用b)标记在表1中。
校准是用具有已知logP值(在两个连续链烷酮之间使用线性内推法通过保留时间测定logP值)的支链烷-2-酮(具有3-16个碳原子)进行的。
λ最大值是用UV光谱在200nm-400nm之间在最大色谱信号测定的。
式(II)原料:
将0.80g(2.44mMol)5-氟-2-甲基-4-(3-甲基-2,6-二氧代-4-三氟甲基-3,6-二氢-1(2H)-嘧啶基)-苄腈、0.52g(2.93mMol)N-溴琥珀酰亚胺、0.10g 2,2′-偶氮二异丁腈和50ml四氯化碳的混合物加热至沸,回流18小时,冷却至室温后,从分液漏斗中加到5%浓度的碳酸氢钠水溶液中。分离出水相,用二氯甲烷萃取2次。合并有机相,用硫酸钠干燥并过滤。将溶剂小心地从滤液中减压蒸馏出去。
获得了1.20g(理论的68%,含量为56%)2-溴甲基-5-氟-4-(3-甲基-2,6-二氧代-4-三氟甲基-3,6-二氢-1(2H)-嘧啶基)-苄腈。
1H-NMR(DMSO-D6,δ):4.68ppm。
按照类似于实施例(II-1)的方法,能够制得例如在下表2中所列出的通式(II)化合物。表2:式(II)化合物的实例
式(IV)原料:实施例(IV-1)
实施例编号 | R1 | R2 | R3 | R4 | R5 | X | 物理常数 |
II-2 | CH3 | CF3 | H | F | Br | Br | 1H-NMR(DMSO-D6,δ):4,75ppm |
II-3 | CH3 | CF3 | H | F | Br | Cl | |
II-4 | CH3 | CF3 | H | F | CN | Cl | |
II-5 | CH3 | CF3 | H | H | CN | Cl | |
II-6 | CH3 | CF3 | H | Cl | Cl | Cl | |
II-7 | CH3 | CF3 | H | H | CN | Br | |
II-8 | CH3 | CF3 | Cl | F | CN | Br | |
II-9 | CH3 | CF3 | CH3 | F | CN | Br |
在搅拌下,于室温(约20℃)将2.5g氢化钠加到14.5g(78mMol)3-氨基-4,4,4-三氟-巴豆酸乙酯和200ml N-甲基吡咯烷酮的混合物中,将该混合物在室温搅拌15分钟。然后加入14.3g(52mMol)氨基甲酸N-(4-溴-2-氟-5-甲基苯基)-O-乙基酯,将该反应混合物加热至沸,回流8小时,然后在室温搅拌12小时。将该混合物倒入300ml1N盐酸内,并通过抽滤分离出所得结晶产物。
获得了14.7g(理论的77%)3-(4-溴-2-氟-5-甲基-苯基)-6-三氟甲基-2,4(1H,3H)-嘧啶二酮,熔点为186℃。
实施例(IV-2)
(随后的反应)
将19.4g(53mMol)3-(4-溴-2-氟-5-甲基-苯基)-6-三氟甲基-2,4(1H,3H)-嘧啶二酮、8.0g(63mMol)硫酸二甲酯、11.0g(79mMol)碳酸钾和100ml丙酮的混合物在搅拌下加热回流15小时。然后将该混合物减压浓缩,将残余物置于乙酸乙酯中,用1N盐酸洗涤。用乙酸乙酯将水相再萃取一次。用水洗涤合并的有机相,用硫酸钠干燥,经由硅胶抽滤。将滤液减压浓缩,通过硅胶柱色谱纯化残余物,用氯仿/乙酸乙酯(Vol.:2∶1)-洗脱。
获得了10.0g(理论的50%)3-(4-溴-2-氟-5-甲基-苯基)-1-甲基-6-三氟甲基-2,4(1H,3H)-嘧啶二酮。
1H-NMR(DMSO-D6,δ):6.56ppm。
(随后的反应)
首先在氩气氛下将2.10g(5.5mMol)3-(4-溴-2-氟-5-甲基-苯基)-1-甲基-6-三氟甲基-2,4(1H,3H)-嘧啶二酮置于5ml N,N-二甲基甲酰胺中,使用分水器在160℃加热30分钟。在约70℃加入0.57g(6.3mMol)氰化铜(I),将该反应混合物在150℃搅拌5小时,在室温(约20℃)再搅拌18小时。然后将该混合物减压浓缩,并将残余物与1.34g氯化铁(III)和50ml水混合。用1N盐酸将该混合物酸化,然后在室温搅拌30分钟。用乙酸乙酯萃取该混合物,用水和饱和氯化钠水溶液洗涤有机相,用硫酸钠干燥并过滤。将滤液减压浓缩,用乙醚蒸煮残余物,通过抽滤分离出所得结晶产物。
获得了1.08g(理论的60%)5-氟-2-甲基-4-(3-甲基-2,6-二氧代-4-三氟甲基-3,6-二氢-1(2H)-嘧啶基)-苄腈,熔点为186℃。
1H-NMR(DMSO-D6,δ):6.60ppm。
式(VII)原料:
实施例(VII-1)
将15.0g(74mMol)4-溴-2-氟-5-甲基-苯胺、9.5g(88mMol)氯甲酸乙酯、11.6g吡啶和500ml二氯甲烷的混合物在室温(约20℃)搅拌2小时。再加入0.5ml氯甲酸乙酯,将该混合物再搅拌1小时。然后用1N盐酸洗涤该混合物,用硫酸钠干燥并过滤。将溶剂小心地从滤液中减压蒸馏出来。
获得了14.4g(理论的70%)氨基甲酸N-(4-溴-2-氟-5-甲基-苯基)-O-乙基酯,为油状残余物。
1H-NMR(DMSO-D6,δ):7.61+7.63ppm(d)。
式(VIII)原料:
实施例(VIII-1)
首先将13.5g(108mMol)2-氟-5-甲基-苯胺加到1升二氯甲烷与400ml甲醇的混合物中,并在搅拌下依次分批加入20g碳酸钙(粉末),连续地滴加44.6g(110mMol)苄基三甲基三溴化铵和250ml二氯甲烷/甲醇(Vol.:5∶2)的溶液。将该混合物搅拌直至橙色消失。然后将该混合物过滤,使用旋转蒸发仪将滤液减压浓缩,将残余物与200ml水混合,用甲基叔丁基醚反复萃取。用硫酸镁将合并的有机相干燥,并过滤。将滤液减压浓缩,使用环己烷将残余物结晶。
获得了12.0g(理论的55%)4-溴-2-氟-5-甲基-苯胺,熔点为57℃。
应用实施例:
实施例A
芽前测试
溶剂:5重量份的丙酮
乳化剂:1重量份的烷基芳基聚二醇醚
为了制备活性化合物的合适制剂,将1重量份的活性化合物与上述量的溶剂混合,加入上述量的乳化剂,并用水将该浓缩物稀释至所需浓度。
将测试植物的种子播种在标准土壤中。约24小时后,用上述活性化合物的制剂喷雾该土壤,以使得每单位面积上施加所需量的活性化合物。选择喷雾溶液的浓度,以使得每公顷施加上在1000升水中的所需量的活性化合物。
3周后,通过与未处理对照比较来评估以%损害表示的植物的受损程度。
数据表示:
0%=没有效果(与未处理的对照一样)
100%=完全破坏
在该测试中,例如制备实施例3、4、6、7、8、9、12、13、16、17、18和19的化合物表现出强的抗杂草活性,并且它们当中有某些化合物被农作物例如玉米良好地耐受。
实施例B
芽后测试
溶剂:5重量份的丙酮
乳化剂:1重量份的烷基芳基聚二醇醚
为了制备活性化合物的合适制剂,将1重量份的活性化合物与上述量的溶剂混合,加入上述量的乳化剂,并用水将该浓缩物稀释至所需浓度。
用上述活性化合物的制剂喷雾高5-15cm的测试植物,以使得每单位面积上施加所需量的活性化合物。选择喷雾溶液的浓度,以使得每公顷施加上在1000升水中的所需量的活性化合物。
3周后,通过与未处理对照比较来评估以%损害表示的植物的受损程度。
数据表示:
0%=没有效果(与未处理的对照一样)
100%=完全破坏
在该测试中,例如制备实施例2、3、4、5、6、7、8、9、10、11、12、13、16、17、18和19的化合物表现出强的抗杂草活性,并且它们当中有某些化合物被农作物例如玉米良好地耐受。
Claims (22)
2.权利要求1的式(I)化合物,其特征在于
R1代表氢、氨基,任选被氰基、卤素或C1-C4-烷氧基取代的具有1-4个碳原子的烷基,或分别任选被卤素取代的分别具有2-4个碳原子的链烯基或炔基,
R2代表氰基、羧基、氨基甲酰基、硫代氨基甲酰基,或分别任选被氰基、卤素或C1-C4-烷氧基取代的分别具有1-4个碳原子的烷基或烷氧基-羰基,
R3代表氢、卤素或任选被卤素取代的具有1-4个碳原子的烷基,
R4代表氢、硝基、氰基、C1-C4-烷氧基或卤素,
R5代表氰基、硫代氨基甲酰基、卤素或分别任选被卤素取代的分别具有1-4个碳原子的烷基或烷氧基,
R6代表经由N连接的含有1-4个选自下列的杂原子的4-12元饱和或不饱和单环或二环杂环基:氮原子、氧原子、硫原子、-SO-、-SO2-、-CO-和/或-CS-,所述杂环基可任选被下列基团取代:硝基、羟基、巯基、氨基、氰基、羧基、氨基甲酰基、卤素、C1-C4-烷基、氰基-C1-C4-烷基、羧基-C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基-C1-C4-烷基、C1-C4-烷氧基-羰基-C1-C4-烷基、C1-C4-烷基-氨基羰基-C1-C4-烷基、二-(C1-C4-烷基)-氨基羰基-C1-C4-烷基、C1-C4-烷基-羰基、C1-C4-卤代烷基-羰基、C1-C4-烷氧基-C1-C4-烷基-羰基、C1-C4-烷氧基、氰基-C1-C4-烷氧基、C1-C4-卤代烷氧基、C1-C4-烷氧基-C1-C4-烷氧基、羧基-C1-C4-烷氧基、C1-C4-烷氧基-羰基-C1-C4-烷氧基、C1-C4-烷基氨基羰基-C1-C4-烷氧基、二-(C1-C4-烷基)-氨基羰基-C1-C4-烷氧基、C2-C4-链烯氧基、C2-C4-炔氧基、C1-C4-烷硫基、C1-C4-卤代烷硫基、C1-C4-烷基亚磺酰基、C1-C4-卤代烷基亚磺酰基、C1-C4-烷基磺酰基、C1-C4-卤代烷基磺酰基、C1-C4-烷基-羰基-氨基、C1-C4-烷氧基-羰基-氨基、C1-C4-烷基-磺酰基-氨基、C2-C4-链烯基、C2-C4-卤代链烯基、C2-C4-炔基、C2-C4-链烯氧基、C2-C4-卤代链烯氧基、C2-C4-炔氧基、C2-C4-链烯硫基、C2-C4-卤代链烯硫基、C2-C4-炔硫基、C2-C4-链烯基氨基、C2-C4-炔基氨基、(分别任选被卤素取代的)C3-C6-环烷基、C3-C6-环烷氧基、C3-C6-环烷硫基、C3-C6-环烷基氨基、C3-C6-环烷基-C1-C4-烷基、C3-C6-环烷基-C1-C4-烷氧基、C3-C6-环烷基-C1-C4-烷硫基、C3-C6-环烷基-C1-C4-烷基氨基、(分别任选被硝基、氰基、卤素、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基或C1-C4-卤代烷氧基取代的)苯基、吡啶基、苯氧基、苯硫基、苯基氨基、苄基、苄氧基、苄硫基或苄基氨基。
3.权利要求1的式(I)化合物,其特征在于
R1代表氢、氨基,或分别任选被氰基、氟、氯、甲氧基或乙氧基取代的甲基、乙基、正或异丙基,或分别任选被氟和/或氯取代的丙烯基、丁烯基、丙炔基或丁炔基,
R2代表氰基、羧基、氨基甲酰基、硫代氨基甲酰基,或分别任选被氰基、氟、氯、甲氧基或乙氧基取代的甲基、乙基、正或异丙基、甲氧基羰基、乙氧基羰基、正或异丙氧基羰基,
R3代表氢、氟、氯、溴,或分别任选被氟和/或氯取代的甲基、乙基、正或异丙基,
R4代表氢、甲氧基、乙氧基、硝基、氰基、氟、氯或溴,
R5代表氰基、硫代氨基甲酰基、氟、氯、溴,或分别任选被氟或氯取代的甲基、乙基、正或异丙基、甲氧基、乙氧基、正或异丙氧基,
R6代表经由N连接的饱和或不饱和单环或二环含氮杂环基,所述杂环基选自:吡咯基、吡咯烷基、吡唑基、咪唑基、异噁唑烷基、三唑基、哌啶基、吗啉基、硫代吗啉基、哌嗪基,并且所述杂环基可任选被下列基团取代:硝基、羟基、巯基、氨基、氰基、羧基、氨基甲酰基、氟、氯、溴、碘、甲基、乙基、正或异丙基、正丁基、异丁基、仲丁基或叔丁基、氰基甲基、氰基乙基、氰基正丙基、氰基异丙基、羧基甲基、羧基乙基、羧基正丙基、羧基异丙基、氟甲基、氯甲基、溴甲基、二氟甲基、二氯甲基、三氟甲基、三氯甲基、氟二氯甲基、氯二氟甲基、氟乙基、氯乙基、二氟乙基、二氯乙基、氯氟乙基、三氟乙基、三氯乙基、氟二氯乙基、氯二氟乙基、四氟乙基、氯三氟乙基、二氯二氟乙基、五氟乙基、甲氧基甲基、乙氧基甲基、正或异丙氧基甲基、甲氧基乙基、乙氧基乙基、正或异丙氧基乙基、甲氧基丙基、乙氧基丙基、甲氧基羰基甲基、乙氧基羰基甲基、正或异丙氧基羰基甲基、甲氧基羰基乙基、乙氧基羰基乙基、正或异丙氧基羰基乙基、甲氧基羰基丙基、乙氧基羰基丙基、甲基氨基羰基甲基、乙基氨基羰基甲基、正或异丙基氨基羰基甲基、甲基氨基羰基乙基、乙基氨基羰基乙基、正或异丙基氨基羰基乙基、二甲基氨基羰基甲基、二甲基氨基羰基乙基、乙酰基、丙酰基、正或异丁酰基、三氟乙酰基、氯乙酰基、二氯乙酰基、三氯乙酰基、甲氧基乙酰基、乙氧基乙酰基、甲氧基、乙氧基、正或异丙氧基、氰基甲氧基、氰基乙氧基、氰基正丙氧基、氰基异丙氧基、氟甲氧基、二氟甲氧基、三氟甲氧基、氟二氯甲氧基、氯二氟甲氧基、氟乙氧基、氯乙氧基、二氟乙氧基、二氯乙氧基、氯氟乙氧基、三氟乙氧基、三氯乙氧基、氟二氯乙氧基、氯二氟乙氧基、甲氧基甲氧基、乙氧基甲氧基、正或异丙氧基甲氧基、甲氧基乙氧基、乙氧基乙氧基、正或异丙氧基乙氧基、羧基甲氧基、羧基乙氧基、甲氧基羰基甲氧基、乙氧基羰基甲氧基、正或异丙氧基羰基甲氧基、甲氧基羰基乙氧基、乙氧基羰基乙氧基、正或异丙氧基羰基乙氧基、甲基氨基羰基甲氧基、乙基氨基羰基甲氧基、正或异丙基氨基羰基甲氧基、甲基氨基羰基乙氧基、乙基氨基羰基乙氧基、正或异丙基氨基羰基乙氧基、二甲基氨基羰基甲氧基、二甲基氨基羰基乙氧基、甲氧基羰基、乙氧基羰基、正或异丙氧基羰基、丙烯氧基、丁烯氧基、丙炔氧基、丁炔氧基、甲硫基、乙硫基、正或异丙硫基、二氟甲硫基、三氟甲硫基、氟二氯甲硫基、氯二氟甲硫基、甲基亚磺酰基、乙基亚磺酰基、正或异丙基亚磺酰基、三氟甲基亚磺酰基、甲基磺酰基、乙基磺酰基、正或异丙基磺酰基、三氟甲基磺酰基、(分别任选被氟、氯、甲氧基或乙氧基取代的)乙酰基氨基、丙酰基氨基、正或异丁酰基氨基、甲氧基羰基氨基、乙氧基羰基氨基、正或异丙氧基羰基氨基、(分别任选被氟和/或氯取代的)甲基磺酰基氨基、乙基磺酰基氨基、正或异丙基磺酰基氨基、(分别任选被氟和/或氯取代的)环丙基、环丁基、环戊基、环己基、环丙氧基、环丁氧基、环戊氧基、环己氧基、环丙硫基、环丁硫基、环戊硫基、环己硫基、环丙基氨基、环丁基氨基、环戊基氨基、环己基氨基、环丙基甲基、环丁基甲基、环戊基甲基、环己基甲基、环丙基甲氧基、环丁基甲氧基、环戊基甲氧基、环己基甲氧基、环丙基甲硫基、环丁基甲硫基、环戊基甲硫基、环己基甲硫基、环丙基甲基氨基、环丁基甲基氨基、环戊基甲基氨基、环己基甲基氨基、(分别任选被硝基、氰基、氟、氯、溴、甲基、乙基、正或异丙基、正丁基、异丁基、仲丁基或叔丁基、三氟甲基、甲氧基、乙氧基、正或异丙氧基、二氟甲氧基或三氟甲氧基取代的)苯基、吡啶基、苯氧基、苯硫基、苯基氨基、苄基、苄氧基、苄硫基或苄基氨基,
或代表一个下列基团:
Q代表氧或硫,
R7代表氢、羟基、巯基、氰基、氟、氯、溴、碘;代表分别任选被氟、氯、甲氧基、乙氧基、正或异丙氧基、甲硫基、乙硫基、正或异丙硫基、甲基亚磺酰基、乙基亚磺酰基、正或异丙基亚磺酰基、甲基磺酰基、乙基磺酰基、正或异丙基磺酰基取代的下列基团:甲基、乙基、正或异丙基、正丁基、异丁基、仲丁基或叔丁基、甲氧基、乙氧基、正或异丙氧基、正丁氧基、异丁氧基、仲丁氧基或叔丁氧基、甲硫基、乙硫基、正或异丙硫基、正丁硫基、异丁硫基、仲丁硫基或叔丁硫基、甲基亚磺酰基、乙基亚磺酰基、正或异丙基亚磺酰基、甲基磺酰基、乙基磺酰基、正或异丙基磺酰基;代表甲基氨基、乙基氨基、正或异丙基氨基、正丁基氨基、异丁基氨基、仲丁基氨基或叔丁基氨基、二甲基氨基、二乙基氨基、二正丙基氨基或二异丙基氨基;代表分别任选被氟和/或氯取代的乙烯基、丙烯基、丁烯基、乙炔基、丙炔基、丁炔基、丙烯氧基、丁烯氧基、丙烯硫基、丁烯硫基、丙烯基氨基或丁烯基氨基;代表分别任选被氟和/或氯取代的环丙基、环丁基、环戊基、环己基、环丙氧基、环丁氧基、环戊氧基、环己氧基、环丙硫基、环丁硫基、环戊硫基、环己硫基、环丙基氨基、环丁基氨基、环戊基氨基、环己基氨基、环丙基甲基、环丁基甲基、环戊基甲基、环己基甲基、环丙基甲氧基、环丁基甲氧基、环戊基甲氧基、环己基甲氧基、环丙基甲硫基、环丁基甲硫基、环戊基甲硫基、环己基甲硫基、环丙基甲基氨基、环丁基甲基氨基、环戊基甲基氨基或环己基甲基氨基;或代表分别任选被氟、氯、甲基、乙基、正或异丙基、正丁基、异丁基、仲丁基或叔丁基、甲氧基、乙氧基、正或异丙氧基取代的苯基、苯氧基、苯硫基、苯基氨基、苄基、苄氧基、苄硫基或苄基氨基,且
R8代表氢、羟基、氨基;代表分别任选被氟和/或氯、甲氧基或乙氧基取代的甲基、乙基、正或异丙基、正丁基、异丁基或仲丁基、甲氧基、乙氧基、正或异丙氧基、甲基氨基、乙基氨基或二甲基氨基;代表分别任选被氟和/或氯取代的乙烯基、丙烯基、乙炔基、丙炔基或丙烯氧基;代表分别任选被氟和/或氯取代的环丙基、环丁基、环戊基、环己基、环丙基甲基、环丁基甲基、环戊基甲基或环己基甲基;或代表分别任选被氟、氯、甲基、乙基、正或异丙基、正丁基、异丁基、仲丁基或叔丁基、甲氧基、乙氧基、正或异丙氧基取代的苯基或苄基。
4.权利要求1的式(I)化合物,其特征在于
R1代表氢、氨基或甲基,
R2代表氰基、羧基、氨基甲酰基、硫代氨基甲酰基;代表分别任选被氟和/或氯取代的甲基或乙基;或代表甲氧基羰基或乙氧基羰基,
R3代表氢、氟、氯、溴;或代表任选被氟和/或氯取代的甲基,
R4代表氢、氟或氯,
R5代表氰基、硫代氨基甲酰基、氯、溴;或代表分别任选被氟和/或氯取代的甲基或甲氧基,
R6代表经由N连接的饱和或不饱和单环或二环含氮杂环基,所述杂环基选自:吡咯基、吡咯烷基、吡唑基、咪唑基、异噁唑烷基、三唑基、哌啶基、吗啉基、硫代吗啉基、哌嗪基,并且所述杂环基可任选被下列基团取代:硝基、羟基、巯基、氨基、氰基、羧基、氨基甲酰基、氟、氯、溴、碘、甲基、乙基、正或异丙基、正丁基、异丁基、仲丁基或叔丁基、氰基甲基、氰基乙基、氰基正丙基、氰基异丙基、羧基甲基、羧基乙基、羧基正丙基、羧基异丙基、氟甲基、氯甲基、溴甲基、二氟甲基、二氯甲基、三氟甲基、三氯甲基、氟二氯甲基、氯二氟甲基、氟乙基、氯乙基、二氟乙基、二氯乙基、氯氟乙基、三氟乙基、三氯乙基、氟二氯乙基、氯二氟乙基、四氟乙基、氯三氟乙基、二氯二氟乙基、五氟乙基、甲氧基甲基、乙氧基甲基、正或异丙氧基甲基、甲氧基乙基、乙氧基乙基、正或异丙氧基乙基、甲氧基丙基、乙氧基丙基、甲氧基羰基甲基、乙氧基羰基甲基、正或异丙氧基羰基甲基、甲氧基羰基乙基、乙氧基羰基乙基、正或异丙氧基羰基乙基、甲氧基羰基丙基、乙氧基羰基丙基、甲基氨基羰基甲基、乙基氨基羰基甲基、正或异丙基氨基羰基甲基、甲基氨基羰基乙基、乙基氨基羰基乙基、正或异丙基氨基羰基乙基、二甲基氨基羰基甲基、二甲基氨基羰基乙基、甲氧基、乙氧基、正或异丙氧基、氰基甲氧基、氰基乙氧基、氰基正丙氧基、氰基异丙氧基、氟甲氧基、二氟甲氧基、三氟甲氧基、氟二氯甲氧基、氯二氟甲氧基、氟乙氧基、氯乙氧基、二氟乙氧基、二氯乙氧基、氯氟乙氧基、三氟乙氧基、三氯乙氧基、氟二氯乙氧基、氯二氟乙氧基、甲氧基甲氧基、乙氧基甲氧基、正或异丙氧基甲氧基、甲氧基乙氧基、乙氧基乙氧基、正或异丙氧基乙氧基、羧基甲氧基、羧基乙氧基、甲氧基羰基甲氧基、乙氧基羰基甲氧基、正或异丙氧基羰基甲氧基、甲氧基羰基乙氧基、乙氧基羰基乙氧基、正或异丙氧基羰基乙氧基、甲基氨基羰基甲氧基、乙基氨基羰基甲氧基、正或异丙基氨基羰基甲氧基、甲基氨基羰基乙氧基、乙基氨基羰基乙氧基、正或异丙基氨基羰基乙氧基、二甲基氨基羰基甲氧基、二甲基氨基羰基乙氧基、丙烯氧基、丁烯氧基、丙炔氧基、丁炔氧基、甲硫基、乙硫基、正或异丙硫基、二氟甲硫基、三氟甲硫基、氟二氯甲硫基、氯二氟甲硫基、甲基亚磺酰基、乙基亚磺酰基、正或异丙基亚磺酰基、三氟甲基亚磺酰基、甲基磺酰基、乙基磺酰基、正或异丙基磺酰基、三氟甲基磺酰基、(分别任选被氟、氯、甲氧基或乙氧基取代的)乙酰基氨基、丙酰基氨基、正或异丁酰基氨基、甲氧基羰基氨基、乙氧基羰基氨基、正或异丙氧基羰基氨基、(分别任选被氟和/或氯取代的)甲基磺酰基氨基、乙基磺酰基氨基、正或异丙基磺酰基氨基、(分别任选被氟和/或氯取代的)环丙基、环丁基、环戊基、环己基、环丙氧基、环丁氧基、环戊氧基、环己氧基、环丙硫基、环丁硫基、环戊硫基、环己硫基、环丙基氨基、环丁基氨基、环戊基氨基、环己基氨基、环丙基甲基、环丁基甲基、环戊基甲基、环己基甲基、环丙基甲氧基、环丁基甲氧基、环戊基甲氧基、环己基甲氧基、环丙基甲硫基、环丁基甲硫基、环戊基甲硫基、环己基甲硫基、环丙基甲基氨基、环丁基甲基氨基、环戊基甲基氨基、环己基甲基氨基、(分别任选被硝基、氰基、氟、氯、溴、甲基、乙基、正或异丙基、正丁基、异丁基、仲丁基或叔丁基、三氟甲基、甲氧基、乙氧基、正或异丙氧基、二氟甲氧基或三氟甲氧基取代的)苯基、苯氧基、苯硫基、苯基氨基、苄基、苄氧基、苄硫基或苄基氨基,
或代表一个下列基团:
Q优选代表氧,
R7代表氢、羟基、巯基、氰基、氟、氯;代表分别任选被氟、氯、甲氧基、乙氧基、甲硫基或乙硫基取代的甲基或乙基、甲氧基、乙氧基或甲硫基;代表甲基氨基、乙基氨基、二甲基氨基或二乙基氨基;代表分别任选被氟和/或氯取代的环丙基、环丁基、环戊基、环己基、环丙氧基、环丁氧基、环戊氧基或环己氧基;或代表分别任选被氟、氯、甲基、乙基、甲氧基或乙氧基取代的苯基、苯氧基、苄基或苄氧基,和
R8代表氢、羟基、氨基;代表分别任选被氟和/或氯、甲氧基或乙氧基取代的甲基或乙基、甲氧基、乙氧基、甲基氨基、乙基氨基或二甲基氨基;代表分别任选被氟和/或氯取代的环丙基、环丁基、环戊基、环己基、环丙基甲基、环丁基甲基、环戊基甲基或环己基甲基;或代表分别任选被氟、氯、甲基、乙基、甲氧基或乙氧基取代的苯基或苄基。
5.权利要求1的式(I)化合物,其特征在于,
R2代表分别被氟和/或氯取代的甲基、乙基;或代表甲氧基羰基或乙氧基羰基,
R3代表氢、氟、氯;或代表任选被氟和/或氯取代的甲基,
R5代表氰基、氯或溴,和
R6代表经由N连接的杂环基,所述杂环基选自:吡咯烷基、异噁唑烷基、哌啶基、吗啉基、硫代吗啉基、哌嗪基,并且所述杂环基可任选被下列基团取代:羟基、氨基、氟、氯、甲基、乙基、三氟甲基、甲硫基、乙硫基、甲基氨基、二甲基氨基、二乙基氨基、环丙基、环丁基、环戊基或环己基;
或代表一个下列基团
6.权利要求1的式(I)化合物,其特征在于,
R1代表氢、氨基或甲基,
R2代表氰基或三氟甲基,
R3代表氢、氟、氯或甲基,
R4代表氢、氟或氯,
R5代表氰基、硫代氨基甲酰基、氯或溴,
R6代表下式所示基团
Q代表氧,
R7代表氢、氯、溴、碘;代表分别任选被氟、氯、甲氧基、乙氧基、甲硫基、乙硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基或乙基磺酰基取代的甲基、乙基、正或异丙基、甲氧基、乙氧基、正或异丙氧基、甲硫基、乙硫基、正或异丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基、乙基磺酰基;代表甲基氨基、乙基氨基、正或异丙基氨基、二甲基氨基或二乙基氨基;代表分别任选被氟和/或氯取代的乙烯基、丙烯基、乙炔基、丙炔基、丙烯氧基、丙烯硫基或丙烯基氨基;代表任选被氟和/或氯取代的环丙基;或代表分别任选被氟、氯、甲基、乙基、甲氧基或乙氧基取代的苯基、苯氧基、苯硫基、苯基氨基、苄基、苄氧基、苄硫基或苄基氨基,且
R8代表氢、氨基;代表分别任选被氟和/或氯、甲氧基或乙氧基取代的甲基、乙基、正或异丙基、甲氧基、乙氧基、正或异丙氧基;代表任选被氟和/或氯取代的环丙基;或代表分别任选被氟、氯、甲基、乙基、甲氧基或乙氧基取代的苯基或苄基。
7.权利要求1-6任一项的式(I)化合物的钠盐、钾盐、镁盐、钙盐、铵盐、C1-C4-烷基铵盐、二-(C1-C4-烷基)-铵盐、三-(C1-C4-烷基)-铵盐、四-(C1-C4-烷基)-铵盐、三-(C1-C4-烷基)-锍盐、C5-或C6-环烷基-铵盐和二-(C1-C2-烷基)-苄基-铵盐,以及这些化合物与金属例如铜、铁、钴或镍的络合化合物。
8.制备权利要求1-7任一项的式(I)化合物的方法,其特征在于,
将通式(II)化合物
其中
R1、R2、R3、R4和R5分别如权利要求1-6任一项所定义,且
X代表卤素,
与通式(III)氮杂环化合物反应,
H-R6 (III)
其中
R6如权利要求1-6任一项所定义,
任选在一种或多种反应辅助剂存在下,以及任选在一种或多种稀释剂存在下进行该反应,
并且任选,随后以常规方式将所得通式(I)化合物转化成在取代基定义范围内的其它通式(I)化合物。
9.通式(II)化合物
其中
R1、R2、R3、R4和R5分别如权利要求1-6任一项所定义,且
X代表卤素。
10.制备权利要求9的式(II)化合物的方法,其特征在于将通式(IV)化合物
其中
R1、R2、R3、R4和R5分别如权利要求1-6任一项所定义,
与卤化剂于50℃-100℃的温度下反应,任选在反应辅助剂存在下,以及任选在稀释剂存在下进行该反应。
11.式(IV)化合物
其中
R1、R2、R3、R4和R5分别如权利要求1-6任一项所定义。
12.制备权利要求11的式(IV)化合物的方法,其特征在于
将通式(V)化合物
其中
R1、R2和R3分别如权利要求1-6任一项所定义,且
R代表烷基、芳基或芳基烷基,
与通式(VI)化合物
其中
R4和R5分别如权利要求1-6任一项所定义,
或者与通式(VII)化合物于0℃-150℃温度下反应
其中
R4和R5分别如权利要求1-6任一项所定义,且
R代表烷基、芳基或芳基烷基,
任选在反应辅助剂存在下,以及任选在稀释剂存在下进行该反应,
并且任选,随后以常规方式将所得通式(IV)化合物转化成在取代基定义范围内的其它通式(IV)化合物。
14.制备权利要求13的式(VI)化合物的方法,其特征在于
将通式(VIII)化合物
其中
R4和R5分别如权利要求1-6任一项所定义,
与光气在稀释剂存在下于-20℃-+150℃温度下反应。
15.式(VII)化合物
其中
R4和R5分别如权利要求1-6任一项所定义,且
R代表烷基、芳基或芳基烷基,
不包括化合物N-(4-溴-3-甲基-苯基)-氨基甲酸O-甲基酯和N-(4-溴-3-甲基-苯基)-氨基甲酸O-乙基酯。
19.农作物处理剂,其特征在于,所述组合物包含至少一种权利要求1的式(I)化合物和常规增容剂。
20.控制不需要的植物的方法,其特征在于,将至少一种权利要求1的式(I)化合物或权利要求19的试剂作用于不需要的植物和/或它们的栖息地。
21.权利要求1的式(I)化合物在控制不需要的植物中的应用。
22.制备除草组合物的方法,其特征在于,将权利要求1的式(I)化合物与增容剂和/或表面活性剂混合。
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DE10051981A DE10051981A1 (de) | 2000-10-20 | 2000-10-20 | Substituierte Phenyluracile |
DE10051981.4 | 2000-10-20 |
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US (1) | US6992044B1 (zh) |
EP (1) | EP1330443A1 (zh) |
JP (1) | JP2004531462A (zh) |
KR (1) | KR20030041166A (zh) |
CN (1) | CN1481369A (zh) |
AR (1) | AR030818A1 (zh) |
AU (2) | AU2002223604B2 (zh) |
BR (1) | BR0114746A (zh) |
CA (1) | CA2425884A1 (zh) |
DE (1) | DE10051981A1 (zh) |
MX (1) | MXPA03003426A (zh) |
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DE10223914A1 (de) * | 2002-05-29 | 2003-12-11 | Bayer Cropscience Ag | Substituierte Phenyluracile |
PE20120519A1 (es) * | 2009-03-24 | 2012-06-03 | Abbvie Bahamas Ltd | Proceso para preparar (e)-n-(4-(3-tertbutil-5-(2, 4-dioxo-3, 4-dihidropirimidin-1 (2h)-il)-2-metoxiestiril)fenil)metanosulfonamida |
CN105753853B (zh) | 2014-12-16 | 2020-08-04 | 沈阳中化农药化工研发有限公司 | 一种含异恶唑啉的脲嘧啶类化合物及其用途 |
CN110964001B (zh) * | 2018-09-29 | 2022-07-22 | 沈阳中化农药化工研发有限公司 | 一种甲基化制备含异恶唑啉脲嘧啶类化合物的方法 |
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CA1076114A (en) | 1975-02-10 | 1980-04-22 | Mitsubishi Chemical Industries Limited | 1,5-alkylene-3-aryl hydantoin derivatives |
US4191775A (en) | 1977-12-15 | 1980-03-04 | Imperial Chemical Industries Limited | Amide derivatives |
AU2328188A (en) * | 1987-09-23 | 1989-04-18 | Ciba-Geigy Ag | Heterocyclic compounds |
DE59007059D1 (de) | 1989-06-29 | 1994-10-13 | Ciba Geigy Ag | Heterocyclische verbindungen. |
US5084084A (en) | 1989-07-14 | 1992-01-28 | Nissan Chemical Industries Ltd. | Uracil derivatives and herbicides containing the same as active ingredient |
AU627906B2 (en) | 1989-07-14 | 1992-09-03 | Nissan Chemical Industries Ltd. | Uracil derivatives and herbicides containing the same as active ingredient |
US4979982A (en) | 1990-02-02 | 1990-12-25 | Uniroyal Chemical Company, Inc. | Herbicidal cinnamic ester uracils |
JP3089621B2 (ja) | 1990-12-17 | 2000-09-18 | 日産化学工業株式会社 | ウラシル誘導体 |
US5169430A (en) | 1991-08-09 | 1992-12-08 | Uniroyal Chemical Company, Inc. | Benzenesulfonamide derivatives and methods for their production |
US5798316A (en) * | 1992-08-26 | 1998-08-25 | Theodoridis; George | Herbicidal combinations containing 2- (4-heterocyclic-phenoxymethyl)phenoxy!alkanoates |
US5681794A (en) | 1993-08-18 | 1997-10-28 | Bayer Aktiengesellschaft | N-cyanoaryl-nitrogen heterocycles |
ES2110667T3 (es) | 1993-08-18 | 1998-02-16 | Bayer Ag | N-cianoaril-heterociclos nitrogenados. |
CN1175256A (zh) | 1994-12-22 | 1998-03-04 | 史密丝克莱恩比彻姆有限公司 | 四环螺环化合物,其制备方法及其作为5ht1d受体拮抗剂的应用 |
CA2225756C (en) | 1995-06-29 | 2008-09-09 | Bayer Aktiengesellschaft | Substituted cyanophenyl uracils |
DE19524617A1 (de) * | 1995-07-06 | 1997-01-09 | Basf Ag | Benzylhydroxylamine und Zwischenprodukte zu deren Herstellung |
KR19990028722A (ko) * | 1995-07-06 | 1999-04-15 | 스타르크, 카르크 | 벤질히드록실아민 및 그를 제조하는데 사용되는중간체 |
PL335697A1 (en) | 1997-03-14 | 2000-05-08 | Isk Americas Inc | Diaryl ethers and methods of obtaining them as well as herbicidal and dehumidifying compositions containing them |
TR199902590T2 (xx) | 1997-04-18 | 2000-06-21 | Smithkline Beecham P.L.C. | Birle�ik 5HT1A 5HT1B ve 5HT1D resept�r antagonist aktivitesi olan indol t�revleri. |
CN1314894A (zh) | 1998-07-09 | 2001-09-26 | 拜尔公司 | 取代的苯基尿嘧啶类化合物 |
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- 2001-10-08 EP EP01988711A patent/EP1330443A1/de not_active Withdrawn
- 2001-10-08 WO PCT/EP2001/011589 patent/WO2002034725A1/de not_active Application Discontinuation
- 2001-10-08 CA CA002425884A patent/CA2425884A1/en not_active Abandoned
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DE10051981A1 (de) | 2002-05-02 |
EP1330443A1 (de) | 2003-07-30 |
AR030818A1 (es) | 2003-09-03 |
WO2002034725A1 (de) | 2002-05-02 |
KR20030041166A (ko) | 2003-05-23 |
MXPA03003426A (es) | 2005-01-25 |
BR0114746A (pt) | 2004-02-10 |
JP2004531462A (ja) | 2004-10-14 |
PL360152A1 (en) | 2004-09-06 |
CA2425884A1 (en) | 2002-05-02 |
US6992044B1 (en) | 2006-01-31 |
RU2003114858A (ru) | 2004-11-10 |
AU2360402A (en) | 2002-05-06 |
AU2002223604B2 (en) | 2006-11-02 |
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