JPH07502028A - ピリミジニル‐またはトリアジニル‐オキシ‐(または‐チオ)‐アルデヒド誘導体、それらの製造方法および除草剤または植物生長調整剤としての用途 - Google Patents
ピリミジニル‐またはトリアジニル‐オキシ‐(または‐チオ)‐アルデヒド誘導体、それらの製造方法および除草剤または植物生長調整剤としての用途Info
- Publication number
- JPH07502028A JPH07502028A JP5510545A JP51054593A JPH07502028A JP H07502028 A JPH07502028 A JP H07502028A JP 5510545 A JP5510545 A JP 5510545A JP 51054593 A JP51054593 A JP 51054593A JP H07502028 A JPH07502028 A JP H07502028A
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- formula
- phenyl
- substituted
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000004009 herbicide Substances 0.000 title claims description 9
- 239000005648 plant growth regulator Substances 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 103
- 150000001875 compounds Chemical class 0.000 claims description 90
- 229910052739 hydrogen Inorganic materials 0.000 claims description 72
- 239000001257 hydrogen Substances 0.000 claims description 70
- -1 aminocarbonylamino, aminothiocarbonyl Chemical group 0.000 claims description 52
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- 239000000126 substance Substances 0.000 claims description 42
- 150000002431 hydrogen Chemical class 0.000 claims description 39
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 28
- 150000002367 halogens Chemical class 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 28
- 229910052736 halogen Inorganic materials 0.000 claims description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 21
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 20
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 20
- 238000009472 formulation Methods 0.000 claims description 18
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 239000002689 soil Substances 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 11
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 11
- 230000002363 herbicidal effect Effects 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 10
- 239000011734 sodium Substances 0.000 claims description 10
- 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 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 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 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 229910052708 sodium Inorganic materials 0.000 claims description 9
- 230000012010 growth Effects 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000001188 haloalkyl group Chemical group 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 5
- 125000004450 alkenylene group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 4
- 125000005046 dihydronaphthyl group Chemical group 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000004465 cycloalkenyloxy group Chemical group 0.000 claims description 2
- 229910052753 mercury Inorganic materials 0.000 claims description 2
- 238000003541 multi-stage reaction Methods 0.000 claims description 2
- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical compound Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 7
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 6
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 5
- 125000004043 oxo group Chemical group O=* 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- 101150033450 NUF2 gene Proteins 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims 1
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 claims 1
- NFGODEMQGQNUKK-UHFFFAOYSA-M [6-(diethylamino)-9-(2-octadecoxycarbonylphenyl)xanthen-3-ylidene]-diethylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCCOC(=O)C1=CC=CC=C1C1=C2C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C21 NFGODEMQGQNUKK-UHFFFAOYSA-M 0.000 claims 1
- 125000003302 alkenyloxy group Chemical group 0.000 claims 1
- 125000005133 alkynyloxy group Chemical group 0.000 claims 1
- 125000005605 benzo group Chemical group 0.000 claims 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000004965 chloroalkyl group Chemical group 0.000 claims 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000004665 trialkylsilyl group Chemical group 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 46
- 229910052799 carbon Inorganic materials 0.000 description 25
- 239000013543 active substance Substances 0.000 description 23
- 239000000843 powder Substances 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 239000008187 granular material Substances 0.000 description 15
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
- 238000011282 treatment Methods 0.000 description 12
- 239000000839 emulsion Substances 0.000 description 11
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 8
- 230000006378 damage Effects 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical class CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 238000005469 granulation Methods 0.000 description 6
- 230000003179 granulation Effects 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 240000006694 Stellaria media Species 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 5
- 241000894007 species Species 0.000 description 5
- 239000004562 water dispersible granule Substances 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 241000234653 Cyperus Species 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 230000035784 germination Effects 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 229920000151 polyglycol Polymers 0.000 description 4
- 239000010695 polyglycol Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 3
- WMLPCIHUFDKWJU-UHFFFAOYSA-N Cinosulfuron Chemical compound COCCOC1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC)=NC(OC)=N1 WMLPCIHUFDKWJU-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 241000220261 Sinapis Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 239000000084 colloidal system Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 150000002191 fatty alcohols Chemical class 0.000 description 3
- 239000003337 fertilizer Substances 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000000417 fungicide Substances 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 230000000887 hydrating effect Effects 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 238000001694 spray drying Methods 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 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 3
- 239000004546 suspension concentrate Substances 0.000 description 3
- GOCUAJYOYBLQRH-UHFFFAOYSA-N 2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl GOCUAJYOYBLQRH-UHFFFAOYSA-N 0.000 description 2
- WUZNHSBFPPFULJ-UHFFFAOYSA-N 2-[[4-chloro-6-(cyclopropylamino)-1,3,5-triazin-2-yl]amino]-2-methylpropanenitrile Chemical compound N#CC(C)(C)NC1=NC(Cl)=NC(NC2CC2)=N1 WUZNHSBFPPFULJ-UHFFFAOYSA-N 0.000 description 2
- WVQBLGZPHOPPFO-UHFFFAOYSA-N 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(C(C)COC)C(=O)CCl WVQBLGZPHOPPFO-UHFFFAOYSA-N 0.000 description 2
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
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- 235000003343 Brassica rupestris Nutrition 0.000 description 2
- OEYOMNZEMCPTKN-UHFFFAOYSA-N Butamifos Chemical compound CCC(C)NP(=S)(OCC)OC1=CC(C)=CC=C1[N+]([O-])=O OEYOMNZEMCPTKN-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- NLYNUTMZTCLNOO-UHFFFAOYSA-N Chlorbromuron Chemical compound CON(C)C(=O)NC1=CC=C(Br)C(Cl)=C1 NLYNUTMZTCLNOO-UHFFFAOYSA-N 0.000 description 2
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- NPOJQCVWMSKXDN-UHFFFAOYSA-N Dacthal Chemical group COC(=O)C1=C(Cl)C(Cl)=C(C(=O)OC)C(Cl)=C1Cl NPOJQCVWMSKXDN-UHFFFAOYSA-N 0.000 description 2
- 239000005508 Dimethachlor Substances 0.000 description 2
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- RXCPQSJAVKGONC-UHFFFAOYSA-N Flumetsulam Chemical compound N1=C2N=C(C)C=CN2N=C1S(=O)(=O)NC1=C(F)C=CC=C1F RXCPQSJAVKGONC-UHFFFAOYSA-N 0.000 description 2
- 241000209082 Lolium Species 0.000 description 2
- BWPYBAJTDILQPY-UHFFFAOYSA-N Methoxyphenone Chemical compound C1=C(C)C(OC)=CC=C1C(=O)C1=CC=CC(C)=C1 BWPYBAJTDILQPY-UHFFFAOYSA-N 0.000 description 2
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- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
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- GINJFDRNADDBIN-FXQIFTODSA-N bilanafos Chemical compound OC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](N)CCP(C)(O)=O GINJFDRNADDBIN-FXQIFTODSA-N 0.000 description 2
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- 238000009835 boiling Methods 0.000 description 2
- WYKYKTKDBLFHCY-UHFFFAOYSA-N chloridazon Chemical compound O=C1C(Cl)=C(N)C=NN1C1=CC=CC=C1 WYKYKTKDBLFHCY-UHFFFAOYSA-N 0.000 description 2
- NSWAMPCUPHPTTC-UHFFFAOYSA-N chlorimuron-ethyl Chemical group CCOC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(Cl)=CC(OC)=N1 NSWAMPCUPHPTTC-UHFFFAOYSA-N 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- KIEDNEWSYUYDSN-UHFFFAOYSA-N clomazone Chemical compound O=C1C(C)(C)CON1CC1=CC=CC=C1Cl KIEDNEWSYUYDSN-UHFFFAOYSA-N 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 description 2
- 125000004802 cyanophenyl group Chemical group 0.000 description 2
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 description 2
- SCCDDNKJYDZXMM-UHFFFAOYSA-N dimethachlor Chemical compound COCCN(C(=O)CCl)C1=C(C)C=CC=C1C SCCDDNKJYDZXMM-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
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Classifications
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- A61K49/1824—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes particles, e.g. uncoated or non-functionalised microparticles or nanoparticles coated or functionalised microparticles or nanoparticles coated or functionalised nanoparticles
- A61K49/1827—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes particles, e.g. uncoated or non-functionalised microparticles or nanoparticles coated or functionalised microparticles or nanoparticles coated or functionalised nanoparticles having a (super)(para)magnetic core, being a solid MRI-active material, e.g. magnetite, or composed of a plurality of MRI-active, organic agents, e.g. Gd-chelates, or nuclei, e.g. Eu3+, encapsulated or entrapped in the core of the coated or functionalised nanoparticle
- A61K49/1851—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes particles, e.g. uncoated or non-functionalised microparticles or nanoparticles coated or functionalised microparticles or nanoparticles coated or functionalised nanoparticles having a (super)(para)magnetic core, being a solid MRI-active material, e.g. magnetite, or composed of a plurality of MRI-active, organic agents, e.g. Gd-chelates, or nuclei, e.g. Eu3+, encapsulated or entrapped in the core of the coated or functionalised nanoparticle having a (super)(para)magnetic core coated or functionalised with an organic macromolecular compound, i.e. oligomeric, polymeric, dendrimeric organic molecule
- A61K49/1863—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes particles, e.g. uncoated or non-functionalised microparticles or nanoparticles coated or functionalised microparticles or nanoparticles coated or functionalised nanoparticles having a (super)(para)magnetic core, being a solid MRI-active material, e.g. magnetite, or composed of a plurality of MRI-active, organic agents, e.g. Gd-chelates, or nuclei, e.g. Eu3+, encapsulated or entrapped in the core of the coated or functionalised nanoparticle having a (super)(para)magnetic core coated or functionalised with an organic macromolecular compound, i.e. oligomeric, polymeric, dendrimeric organic molecule the organic macromolecular compound being a polysaccharide or derivative thereof, e.g. chitosan, chitin, cellulose, pectin, starch
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- 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
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- A—HUMAN NECESSITIES
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
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- A61K41/0052—Thermotherapy; Hyperthermia; Magnetic induction; Induction heating therapy
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
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- 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
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Abstract
Description
Claims (11)
- 1.一般式(I) ▲数式、化学式、表等があります▼I 〔上式中、 XはOまたはSを意味し、 YおよびZはNまたはCHを意味するが、その際両方の基YおよびZが同時にC Hであることはなく、 RaおよびRbは互いに無関係に水素、アルキル、アルコキシ、アルキルチオ、 ハロゲン、ハロアルコキシ、ハロアルキル、アミノ、アルキルアミノまたはジア ルキルアミノを意味し、 Aは式(A1)ないし(A9) ▲数式、化学式、表等があります▼(A1)▲数式、化学式、表等があります▼ (A2)▲数式、化学式、表等があります▼(A3)▲数式、化学式、表等があ ります▼(A4)▲数式、化学式、表等があります▼(A5)▲数式、化学式、 表等があります▼(A6)▲数式、化学式、表等があります▼(A7)▲数式、 化学式、表等があります▼(A8)▲数式、化学式、表等があります▼(A9) で表される基を意味し、 X1,X2,X3およびX4は互いに無関係にOまたはSを意味し、R1は式 ▲数式、化学式、表等があります▼または▲数式、化学式、表等があります▼で 表される脂肪族または芳香脂肪族基を意味し、R2は水素またはトリアルキルシ リルを意味し、R3はアルキル、アルケニル、アルキニル、アルコキシ、アルケ ニルオキシ、アルキニルオキシ、アルキルチオ(ここで上記の7種の基は互いに 無関係に、未置換であるかまたはアルコキシ、アルキルチオ、アミノ、アルキル アミノ、ジアルキルアミノ、ニトロ、シアノ、ハロゲン、フェニルおよび置換フ ェニルよりなる群から選択された基によってモノ−またはポリ置換されている) を意味するか、アルキルカルボニル、アリールカルボニル、置換アリールカルボ ニル、ヒドロキシ、式NR′R′′(ここにR′およびR′′は互いに無関係に 水素、アルキル、ベンジルまたはフェニルを表す)で表される基、またはアミノ カルボニル、アミノカルボニルアミノ、アミノチオカルボニル、アミノチオカル ボニルアミノ、または シクロアルキル、シクロアルケニル、シクロアルケニルオキシまたはフェニル( ここで上記の4種の基は、互いに無関係に、未置換であるかまたはアルキル、ア ルコキシ、アルキルチオ、アミノ、アルキルアミノ、ジアルキルアミノ、ニトロ 、ハロゲン、シアノ、フェニルおよび置換フェニルよりなる群から選択された基 によってモノ−またはポリ置換されている)を意味し、 R4およびR5は互いに無関係に水素、アルキル、アルケニル、アルキニル、シ クロアルキル、フェニル、置換フェニル、ベンジル、アルキルカルボニルまたは アリールカルボニルを意味し、その際両方の基は同時に水素であることはなく、 または、 R4およびR5は結合されたN−原子と一緒で3−ないし7員の複素環を意味し 、これはN−原子のほかに更にN,OおよびSよりなる群から選択されたその他 のヘテロ原子を含有してもよく、そして1個またはそれ以上のアルキル基または 1個のオキソ基によって置換されていてもよく、R6およびR7は互いに無関係 に水素、アルキル、アルケニル、アルキニル、シクロアルキル、フェニル、置換 フェニル、ベンジル、アルキルカルボニルまたはアリールカルボニルを意味する か、またはR6およびR7は結合された基−X1−CH−X2−と一緒で4−な いし8員の複素環を意味し、これは2種のヘテロ原子のほかに更にN,0および Sよなりる群から選択された他のヘテロ原子を有してもよくそして1個またはそ れ以上のアルキル基によって置換されていてもよく、R8は水素、アルキル、ア ルケニル、アルキニル、シクロアルキル、フェニル、置換フェニル、ベンジル、 アルキルカルボニルまたはアリールカルボニルを意味し、 R9およびR10は互いに無関係に水素、アルキル、アルケニル、アルキニル、 シクロアルキル、フェニル、置換フェニル、ベンジル、アルキルカルボニルまた はアリールカルボニルを意味するか、またはR9およびR10は結合されたN− 原子と一緒で3−ないし7員の複素環を意味し、これは更にN,OおよびSより なる群から選択された他のヘテロ原子を有してもよく、そして1個またはそれ以 上のアルキル基または1個のオキソ基によって置換されていてもよく、 R11およびR12は互いに無関係にヒドロキシ、アルキル、アルコキシ、フェ ニル、置換フェニル、フェノキシまたは置換フェノキシを意味し、R13は水素 またはアルキルを意味し、R14は水素、ハロゲン、アルキル(これは未置換で あるかまたはハロゲン、ヒドロキシ、アルコキシ、アルキルチオ、フェニルまた は置換フェニルよりなる群から選択された1個またはそれ以上の基によって置換 されている)またはヒドロキシ、シアノ、シクロアルキル、アリールを意味し、 その際アリールおよび/またはシクロアルキルは未置換かまたは置換されており 、 R15およびR16は互いに無関係に水素またはアルキルを意味するかまたはR 15およびR16は結合されたC−原子と一緒で3−ないし8員の環を意味し、 これは1個の酸素原子を有してもよくそして1個またはそれ以上のアルキルによ って置換されていてもよく、 R17は水素またはアルキルを意味し、R18はR19と無関係に水素またはア ルキルを意味し、R19はR18と無関係にアルキル、アリールまたは置換アリ ールを意味するかまたは R18およびR19は結合されたアルケニレン基と一緒で3−ないし8員の環を 意味し、これは1個の酸素原子を有してもよくそして1個またはそれ以上のアル キル基によって置換されていてもよく、M+は陽イオンの当量を意味し、そして nは数0ないし1を意味する〕 で表される化合物。
- 2.RaおよびRbが互いに無関係に水素、C1−C4−アルキル、C1−C4 −アルコキシ、C1−C4−アルキルチオ、ハロゲン、C1−C4−ハロアルコ キシ、C1−C4−ハロアルキル、C1−C4−アルキルアミノまたはジ−(C 1−C4−アルキル)アミノを意味することを特徴とする請求の範囲第1項によ る化合物。
- 3.R2が水素またはトリ−(C1−C4−アルキル)−シリルを意味し、R3 がC1−C4−アルキル、C2−C4−アルケニル、C2−C4−アルキニル、 C1−C4−アルコキシ、C2−C4−アルケニルオキシ、C2−C4−アルキ ニルオキシ、C1−C4−アルキルチオ(ここに上記の7種の基は互いに無関係 に、未置換であるかまたはC1−C4−アルコキシ、C1−C4−アルキルチオ 、アミノ、(C1−C4−アルキル)−アミノ、ジ−(C1−C4−アルキル) −アミノ、ニトロ、シアノ、ハロゲン、フェニルおよび置換フェニルよりなる群 から選択された基よってモノ−またはポリ置換されている)、または(C1−C 4−アルキル)−カルボニル、ベンゾイル、置換ベンゾイル、ヒドロキシ、式N R′R′′(ここにR′およびR′′は互いに無関係に水素、C1−C4−アル キル、ベンジルまたはフェニルを表す)で表される基、またはアミノカルボニル 、アミノカルボニルアミノ、アミノチオカルボニル、アミノチオカルボニルアミ ノまたはC2−C6−シクロアルキル、C5−C8−シクロアルケニル、C5− C8−シクロアルケニルオキシ、またはフェニル(ここに最後に挙げた4種の基 は、互いに無関係に、末置換であるかまたはC1−C4−アルキル、C1−C4 −アルコキシ、C1−C4−アルキルチオ、アミノ、(C1−C4−アルキル) ーアミノ、ジ−(C1−C4−アルキル)ーアミノ、ニトロ、ハロゲン、シアノ 、フェニルおよび置換フェニルよりなる群から選択された1種またはそれ以上の 基によってモノ−またはポリ置換されている)を意味し、 R4およびR5が互いに無関係に水素、C1−C4−アルキル、C2−C4−ア ルケニル、C2−C4−アルキニル、C3−C8−シクロアルキル、フェニル、 置換フェニル、ベンジル、(C1−C4−アルキル)ーカルボニルまたはベンゾ イルを意味するが、その際両方の基が同時に水素であることはなく、またはR4 およびR5が結合されたN−原子と一緒で5−ないし6員の複素環を意味し、こ れはN−原子のほかにN,OおよびSよりなる群から選択された1個または2個 の他のヘテロ原子を有してもよく、そして1個またはそれ以上のC1−C4−ア ルキル基および1個のオキソ基によって置換されていてもよく、R6およびR7 が互いに無関係に水素、C1−C4−アルキル、C2−C4−アルケニル、C2 −C4−アルキニル、C3−C8−シクロアルキル、フェニル、置換フェニル、 ベンジル、(C1−C4−アルキル)ーカルボニルまたはベンゾイルを意味する か、またはR6およびR7が結合された基−X1−CH−X2−と一緒で5−な いし6員の複素環を意味し、これは両方のヘテロ原子のほかにN,OおよびSよ りなる群から選択されたもう一つのヘテロ原子を有してもよく、そして1個また はそれ以上のC1−C4−アルキル基によって置換されていてもよく、R8が水 素、C1−C4−アルキル、C2−C4−アルケニル、C2−C4−アルキニル 、C2−C■−シクロアルキル、フェニル、置換フェニル、ベンジル、(C1− C4−アルキル)ーカルボニルまたはベンゾイルを意味し、 R9およびR10が互いに無関係に水素、C1−C4−アルキル、C2−C4− アルケニル、C2−C4−アルキニル、C2−C4−シクロアルキル、フェニル 、置換フェニル、ベンジル、(C1−C4−アルキル)ーカルボニルまたはベン ゾイルを意味するか、またはR9およびR10が結合されたN−原子と一緒で5 −ないし6員の複素環を意味し、これはN−原子のほかにN,OおよびSよりな る群から選択された1個または2個の他のヘテロ原子を有してもよく、そして1 個またはそれ以上のC1−C4−アルキル基および1個のオキソ基によって置換 されていてもよく、R11およびR12から互いに無関係にヒドロキシ、C1− C4−アルキル、C1−C4−アルコキシ、フェニル、置換フェニル、フェノキ シまたは置換フェノキシを意味し、 R13が水素またはC1−C4−アルキルを意味し、R14が水素、ハロゲン、 C1−C■−アルキル(これは未置換であるかまたはハロゲン、ヒドロキシ、C 1−C4−アルコキシ、C1−C4−アルキルチオ、フェニルまたは置換フェニ ルよりなる群から選択された1種またはそれ以上の基によって置換されている) またはC2−C■−シクロアルキル、C5−C■−シクロアルケニル(ここに最 後に挙げた2種の基は未置換であるかまたは1個またはそれ以上のC1−C4− アルキル基によって置換されている)を意味し、R15およびR16が互いに無 関係に水素またはC1−C■−アルキルを意味するかまたは R15およびR16が結合されたC−原子と一緒で5−ないし6員の環を意味し 、これは1個の酸素原子を有してもよく、そして1個またはそれ以上のC1−C 4−アルキル基によって置換されていてもよく、R17が水素またはC1−C4 −アルキルを意味し、R18がR19と無関係に水素またはC1−C4−アルキ ルを意味し、R19がR18と無関係にC1−C4−アルキル、フェニルまたは 置換フェニルを意味するかまたは R18およびR19が結合されたアルケニレン基と一緒で5−または6員の環を 意味し、これは1個の酸素原子を有してもよく、そして1個またはそれ以上のC l−C4−アルキル基によって置換されていてもよく、M+がナトリウムまたは カリウムの陽イオンを意味し、そしてnが数0または1を意味する、 ことを特徴とする請求の範囲第1項または第2項による化合物。
- 4.R2が水素またはトリ−(C1−C2−アルキル)−シリルを意味し、R3 がC1−C4アルキル、C1−C4−アルコキシ(ここに上記の2種の基は互い に無関係に、末置換であるかまたはモノ−またはポリハロゲン化されているかま たはC1−C4−アルコキシ、C1−C4−アルキルチオ、アミノ、(C1−C 4−アルキル)−アミノ、ジ−(C1−C4−アルキル)−アミノ、ニトロ、シ アノ、フェニルおよび置換フェニルによって置換されている)を意味するか、ま たは、(C1−C4−アルキル)−カルボニル、ベンゾイル、置換ベンゾイル、 ヒドロキシ、式NR′R′′(ここにR′およびR′′は互いに無関係に水素、 C1−C4−アルキル、ベンジルまたはフェニルを表す)で表される基、または アミノカルボニル、アミノカルボニルアミノ、アミノチオカルボニル、アミノチ オカルボニルアミノ、シクロペンチル、シクロヘキシル、フェニルまたは置換フ ェニルを意味し、R4およびR5が互いに無関係に水素、C1−C4−アルキル 、シクロペンチル、シクロヘキシル、フェニル、置換フェニル、ベンジル、(C 1−C4−アルキル)−カルボニルまたはベンゾイルを意味するが、その際両方 の基が同時に水素であることはなく、または R4およびR5が結合されたN−原子と一緒で5−または6員の複素環を意味し 、それはN−原子のほかにNおよびOよりなる群から選択されたもう一つのヘテ ロ原子を有していてもよく、そして1個またはそれ以上のメチル基によって置換 されていてもよく、 R6およびR7が互いに無関係に水素、C1−C4−アルキル、C2−C4−ア ルケニル、C2−C4−アルキニル、シクロペンチル、シクロヘキシル、フェニ ル、置換フェニル、ベンジル、(C1−C4−アルキル)−カルボニルまたはベ ンゾイルを意味するかまたは R6およびR7は結合された基−X1−CH−X2−と一緒で5−ないし6員の 複素環を意味し、これは1個またはそれ以上のメチル基によって置換されていて もよく、R6が水素、C1−C4−アルキル、C2−C4−アルケニル、C2− C4−アルキニル、シクロペンチル、シクロヘキシル、フェニル、置換フェニル 、ベンジル、(C1−C4−アルキル)ーカルボニルまたはベンゾイルを意味し 、R9およびR10が互いに無関係に水素、C1−C4−アルキル、シクロペン チル、シクロヘキシル、フェニル、置換フェニル、ベンジル、(C1−C4−ア ルキル)ーカルボニルまたはベンゾイルを意味するかまたはR9およびR10が 結合されたN−原子と一緒で5−ないし6員の複素環を意味し、それはN−原子 のほかにNおよびOよりなる群から選択されたもう一つのヘテロ原子を有しても よく、そして1個またはそれ以上のメチル基によって置換されていてれよく、 R11およびR12が互いに無関係にヒドロキシ、C1−C2−アルキル、C1 −C4−アルコキシ、フェニル、置換フェニル、フェノキシまたは置換フェノキ シを意味し、そして R13が水素またはC1−C2−アルキルを意味する、ことを特徴とする請求の 範囲第1項〜第3項による化合物。
- 5.R1が式 ▲数式、化学式、表等があります▼ {上式中、 R14が水素、ハロゲン、C1−C6−アルキル(これは未置換であるかまたは ハロゲン、ヒドロキシ、C1−C4−アルコキシ、特にメトキシまたはエトキシ 、またはC1−C4−アルキルチオ、フェニルまたは置換フェニルよりなる群か ら選択された1種またはそれ以上の基によって置換されている)、またはC2− C4−シクロアルキル、C5−C■−シクロアルケニル(ここに最後に挙げた2 種の基は未置換であるかまたは1個またはそれ以上のC1−C4−アルキル基に よって置換されている)、またはヒドロキシ、シアノ、フェニル、チエニル、ナ フチルまたはジヒドロナフチル(ここに最後に挙げた4種の基は未置換であるか またはメチル、エチル、メトキシ、エトキシ、トリフルオロメチルまたはハロゲ ンによって置換されている)を意味し、 R15およびR16が互いに無関係に水素またはC1−C4−アルキルを意味す るか、または R16およびR1■が結合されているC−原子と一緒で5−または6員の環を意 味し、これは1個の酸素原子を有してもよくそして1個またはそれ以上のC1− C4−アルキル基によって置換されていてもよい}で表される脂肪族または芳香 脂肪族基であることを特徴とする請求の範囲第1項〜第4項のうちのいずれか一 つによる化合物。
- 6.請求の範囲第1項〜第5項のうちのいずれか一つによる式(I)で表される 化合物を製造する方法において、 a)Aが式(A1)の意味を有しそしてR2がHである場合において、式(II )で表される化合物を式(III)で表される化合物と反応せしめるか▲数式、 化学式、表等があります▼(II)▲数式、化学式、表等があります▼(III )(上記式(II)および(III)において、Ra,Rb,X,Y,Zおよび R1は式(I)において定義されたとおりであり、そしてNuf1は核離脱性基 を表す)、または b)Aが式(A1)の意味を有しそしてR2がHである場合において、式(IV )で表される化合物を式(V)で表される化合物と反応せしめるか▲数式、化学 式、表等があります▼(IV)▲数式、化学式、表等があります▼(V)(上記 式(IV)および(V)において、Ra,Rb,X,Y,ZおよびR1は式(I )において定義されたとおりであり、そしてNuf2は核離脱性基を表す)また は c)式(VI) ▲数式、化学式、表等があります▼(VI)(上式中、Ra,Rb,X,Y,Z およびR1は式(I)において定義されているとおりである)で表される化合物 を、 c1)A=(A2)そしてR2=Hである場合には、式H−(O)mNH−R2 (ここにnは式(A2)において定義されているとおりである)で表される化合 物と、c2)A=(A3)である場合には、式HNR4R6で表される化合物と 、c3)A=(A4)である場合には、式HX1−R6…R7−X2Hで表され る化合物と、c4)A=(A5)である場合には、まず式HNR9R10で表さ れる化合物と反応せしめてA=A6である式(I)の化合物を得、次いで式CI CH2X3R5の化合物と、c5)A=(A6)である場合には、式H−NR9 R10で表される化合物と、c6)A=(A7)である場合には、式MSO3H で表される化合物と、c7)A=(A8)である場合には、式HP(=O)R1 1R12で表される化合物と、そしてc8)A=(A9)である場合には、式H X4−CO−CH(SH)R13で表される化合物と、反応せしめるか、または d)c)において記載された式(VI)で表される化合物を、式HS−(CH2 )3−SHで表される化合物との反応、次いでアルキルリチウムおよびハロゲン 化トリアルキルケイ素との反応およびハロゲン化水銀との反応を包含する多段階 方法において式(I)(ここにA=(A2)そしてR2=トリアルキルシリル) で表される化合物に変換されることを特徴とする上記式(I)の化合物の製造方 法。
- 7.式(VI) ▲数式、化学式、表等があります▼(VI)(上式中、Ra,Rb,X,Y,Z およびR1は請求の範囲第1項〜第5項のうちのいずれか一つによる式(I)に 定義されているとおりである)で表わされる化合物。
- 8.式(II)の化合物を式(III)の化合物と反応せしめるか、▲数式、化 学式、表等があります▼(II)▲数式、化学式、表等があります▼(III) (上記式(II)および(III)において、Ra,Rb,X,Y,ZおよびR 1は第7項による式(VI)に定義されているとおりであり、そしてNuf1は 核離脱性基を表す)または 式(IV)の化合物を式(V)の化合物と反応せしめる▲数式、化学式、表等が あります▼(IV)▲数式、化学式、表等があります▼(V)(上記式(IV) および(V)において、Ra,Rb,X,Y,ZおよびR1は式(VI)におい て定義されたとおりであり、そしてNuf2は核離脱性基を表す)ことを特徴と する第7項による式(VI)の化合物の製造方法。
- 9.請求の範囲第1項〜第5項のうちのいずれか一つによる式(I)の化合物お よび通常の調合助剤を含有することを特徴とする除草剤および植物生長調整剤。
- 10.請求の範囲第1項〜第5項のうちのいずれか一つによる式(I)の化合物 を除草剤または植物生長調整剤として使用する方法。
- 11.請求の範囲第1項〜第5項のうちのいずれか一つによる式(I)で表され る1種またはそれ以上の化合物を植物、植物の種子または植物が生育している土 壌の表面またはその中に適用することを特徴とする有害植物の防除または植物の 生長調整方法。
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-
1992
- 1992-06-08 CA CA002089148A patent/CA2089148C/en not_active Expired - Lifetime
- 1992-06-08 ES ES92911159T patent/ES2110500T3/es not_active Expired - Lifetime
- 1992-06-08 DE DE69223748T patent/DE69223748T2/de not_active Expired - Lifetime
- 1992-06-08 DE DE2001199064 patent/DE10199064I2/de active Active
- 1992-06-08 JP JP4510545A patent/JP2939336B2/ja not_active Expired - Lifetime
- 1992-06-08 WO PCT/JP1992/000735 patent/WO1992022586A1/ja active IP Right Grant
- 1992-06-08 DK DK92911159T patent/DK0543020T3/da active
- 1992-06-08 US US07/971,760 patent/US5424419A/en not_active Expired - Lifetime
- 1992-06-08 EP EP92911159A patent/EP0543020B1/en not_active Expired - Lifetime
- 1992-06-08 AU AU18846/92A patent/AU652060C/en not_active Ceased
- 1992-06-08 AT AT92911159T patent/ATE161546T1/de active
-
1993
- 1993-02-10 NO NO930465A patent/NO304351B1/no not_active IP Right Cessation
-
2002
- 2002-04-11 NL NL300087C patent/NL300087I1/nl unknown
- 2002-05-16 NO NO2002002C patent/NO2002002I2/no unknown
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2003
- 2003-01-24 LU LU91004C patent/LU91004I2/en unknown
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NO930465L (no) | 1993-04-06 |
DK0543020T3 (da) | 1998-08-31 |
DE69223748T2 (de) | 1998-04-23 |
US5424419A (en) | 1995-06-13 |
ES2110500T3 (es) | 1998-02-16 |
DE10199064I1 (de) | 2002-02-21 |
EP0543020A1 (en) | 1993-05-26 |
NO930465D0 (no) | 1993-02-10 |
ATE161546T1 (de) | 1998-01-15 |
NO304351B1 (no) | 1998-12-07 |
JP2939336B2 (ja) | 1999-08-25 |
CA2089148A1 (en) | 1992-12-12 |
EP0543020B1 (en) | 1997-12-29 |
CA2089148C (en) | 2003-08-05 |
DE69223748D1 (de) | 1998-02-05 |
WO1992022586A1 (en) | 1992-12-23 |
NL300087I1 (nl) | 2002-07-01 |
AU652060C (en) | 2004-04-22 |
DE10199064I2 (de) | 2004-07-12 |
AU1884692A (en) | 1993-01-12 |
LU91004I2 (en) | 2003-03-24 |
EP0543020A4 (en) | 1993-12-01 |
NO2002002I2 (no) | 2004-09-27 |
AU652060B2 (en) | 1994-08-11 |
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