JP2001508458A - 3−ヘテロシクリル−置換ベンゾイル誘導体 - Google Patents
3−ヘテロシクリル−置換ベンゾイル誘導体Info
- Publication number
- JP2001508458A JP2001508458A JP53362098A JP53362098A JP2001508458A JP 2001508458 A JP2001508458 A JP 2001508458A JP 53362098 A JP53362098 A JP 53362098A JP 53362098 A JP53362098 A JP 53362098A JP 2001508458 A JP2001508458 A JP 2001508458A
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- compounds
- substituted
- hydrogen
- alkoxy
- 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
- 125000003236 benzoyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 title claims abstract description 55
- -1 NR 9 Inorganic materials 0.000 claims abstract description 610
- 239000001257 hydrogen Substances 0.000 claims abstract description 159
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 159
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 100
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 97
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 72
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 59
- 239000000203 mixture Substances 0.000 claims abstract description 55
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 45
- 150000002367 halogens Chemical class 0.000 claims abstract description 44
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 36
- 238000000034 method Methods 0.000 claims abstract description 30
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 24
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 125000004995 haloalkylthio group Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 595
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 98
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 57
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 37
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 36
- 239000001301 oxygen Substances 0.000 claims description 36
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 21
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 17
- 230000002363 herbicidal effect Effects 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 14
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 11
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 239000004009 herbicide Substances 0.000 claims description 11
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 9
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 8
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 8
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 150000001721 carbon Chemical group 0.000 claims description 6
- 229940095102 methyl benzoate Drugs 0.000 claims description 6
- CPLDIWZIQNXJME-UHFFFAOYSA-N CC1=NN(C)C(O)=C1C(=O)C1=CC=C(S(C)(=O)=O)C(C=2CC(ON=2)C#N)=C1Cl Chemical compound CC1=NN(C)C(O)=C1C(=O)C1=CC=C(S(C)(=O)=O)C(C=2CC(ON=2)C#N)=C1Cl CPLDIWZIQNXJME-UHFFFAOYSA-N 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 230000007062 hydrolysis Effects 0.000 claims description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 5
- 238000006467 substitution reaction Methods 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 5
- PXVQWKUYBMZLRB-UHFFFAOYSA-N CC1=NN(C)C(O)=C1C(=O)C1=CC=C(S(C)(=O)=O)C(C=2SCCN=2)=C1Cl Chemical compound CC1=NN(C)C(O)=C1C(=O)C1=CC=C(S(C)(=O)=O)C(C=2SCCN=2)=C1Cl PXVQWKUYBMZLRB-UHFFFAOYSA-N 0.000 claims description 4
- 230000036961 partial effect Effects 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 3
- 238000006462 rearrangement reaction Methods 0.000 claims description 3
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims description 2
- 125000005605 benzo group Chemical class 0.000 claims description 2
- 239000012752 auxiliary agent Substances 0.000 claims 2
- 239000011814 protection agent Substances 0.000 claims 2
- 150000001555 benzenes Chemical class 0.000 claims 1
- 230000000269 nucleophilic effect Effects 0.000 claims 1
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 abstract description 7
- 125000004414 alkyl thio group Chemical group 0.000 abstract description 5
- 239000000543 intermediate Substances 0.000 abstract description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 abstract description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract description 2
- 125000004663 dialkyl amino group Chemical group 0.000 abstract description 2
- 125000001188 haloalkyl group Chemical group 0.000 abstract description 2
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 abstract 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 156
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 100
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 49
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 42
- 239000000460 chlorine Substances 0.000 description 37
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 35
- 229910052801 chlorine Inorganic materials 0.000 description 34
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 33
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 26
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 26
- 239000002904 solvent Substances 0.000 description 22
- 229910052794 bromium Inorganic materials 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- 239000002253 acid Substances 0.000 description 18
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 18
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 17
- 241000196324 Embryophyta Species 0.000 description 17
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 17
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 16
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 14
- 239000013543 active substance Substances 0.000 description 13
- 239000002585 base Substances 0.000 description 13
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 13
- 125000006124 n-propyl sulfonyl group Chemical group 0.000 description 13
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 12
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 11
- 239000011737 fluorine Substances 0.000 description 11
- 229910052731 fluorine Inorganic materials 0.000 description 11
- 239000010410 layer Substances 0.000 description 11
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 11
- 125000006126 n-butyl sulfonyl group Chemical group 0.000 description 11
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 11
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 9
- 150000002825 nitriles Chemical class 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
- 235000010233 benzoic acid Nutrition 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- 239000012141 concentrate Substances 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- 239000011630 iodine Substances 0.000 description 7
- 229910052740 iodine Inorganic materials 0.000 description 7
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 7
- 230000002829 reductive effect Effects 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 231100000331 toxic Toxicity 0.000 description 7
- 230000002588 toxic effect Effects 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- 239000005711 Benzoic acid Substances 0.000 description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 6
- 239000004359 castor oil Substances 0.000 description 6
- 235000019438 castor oil Nutrition 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 6
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 235000013312 flour Nutrition 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000001632 sodium acetate Substances 0.000 description 5
- 235000017281 sodium acetate Nutrition 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 229910052727 yttrium Inorganic materials 0.000 description 5
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 241000209140 Triticum Species 0.000 description 4
- 235000021307 Triticum Nutrition 0.000 description 4
- 240000008042 Zea mays Species 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 4
- 150000003863 ammonium salts Chemical class 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
- 150000002191 fatty alcohols Chemical class 0.000 description 4
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 4
- 125000001072 heteroaryl group Chemical group 0.000 description 4
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- 239000006187 pill Substances 0.000 description 4
- 229920000151 polyglycol Polymers 0.000 description 4
- 239000010695 polyglycol Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- HKPUZZOQHBYMPZ-UHFFFAOYSA-N 1-$l^{1}-sulfanylpropane Chemical compound CCC[S] HKPUZZOQHBYMPZ-UHFFFAOYSA-N 0.000 description 3
- ZSHNSXSONOHWNB-UHFFFAOYSA-N 1-(2-chloro-3-methyl-4-methylsulfanylphenyl)ethanone Chemical compound CSC1=CC=C(C(C)=O)C(Cl)=C1C ZSHNSXSONOHWNB-UHFFFAOYSA-N 0.000 description 3
- NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical class CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- WTNMMKJWWSEFNO-UHFFFAOYSA-N CC(C)[S] Chemical compound CC(C)[S] WTNMMKJWWSEFNO-UHFFFAOYSA-N 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 3
- 244000299507 Gossypium hirsutum Species 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- 240000007594 Oryza sativa Species 0.000 description 3
- 238000000297 Sandmeyer reaction Methods 0.000 description 3
- 239000005708 Sodium hypochlorite Substances 0.000 description 3
- 235000002595 Solanum tuberosum Nutrition 0.000 description 3
- 244000061456 Solanum tuberosum Species 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- 150000008041 alkali metal carbonates Chemical class 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 3
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
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- JWHOQZUREKYPBY-UHFFFAOYSA-N rubonic acid Natural products CC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CCC(=O)C(C)(C)C5CC(=O)C34C)C2C1)C(=O)O JWHOQZUREKYPBY-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
- C07D411/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D411/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/20—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings condensed with carbocyclic rings or ring systems
-
- 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
- C07D403/12—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 chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
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Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.一般式I で表され、式中 R1、R2が水素、ニトロ、ハロゲン、シアノ、C1−C6アルキル、C1−C6ハ ロアルキル、C1−C6アルコキシ、C1−C6ハロアルコキシ、C1−C6アルキル チオ、C1−C6ハロアルキルチオ、C1−C6アルキルスルフィニル、C1−C6ハ ロアルキルスルフィニル、C1−C6アルキルスルホニルまたはC1−C6ハロアル キルスルホニル、 R3が水素、ハロゲンまたはC1−C6アルキル、 R4、R5が水素、ハロゲン、シアノ、ニトロ、C1−C4アルキル、C1−C4ア ルコキシ−C1−C4アルキル、ジ(C1−C4アルコキシ)−C1−C4アルキル、 ジ(C1−C4アルキル)−アミノ−C1−C4アルキル、[2,2−ジ(C1−C4 アルキル)−1−ヒドラジノ]−C1−C4アルキル、C1−C6アルキルイミノオ キシ−C1−C4アルキル、C1−C4アルコキシカルボニル−C1−C4アルキル、 C1−C4アルキルチオ−C1−C4アルキル、C1−C4ハロアルキル、C1−C4シ アノアルキル、C3−C8シクロアルキル、C1−C4アルコキシ、C1−C4アルコ キシ−C2−C4アルコキシ、C1−C4ハロアルコキシ、ヒドロキシル、C1−C4 アルキルカルボニルオキシ、C1−C4アルキルチオ、C1−C4ハロアルキルチオ 、ジ(C1−C4アルキル)アミノ、COR6、フェニルまたはベンジルを意味し 、最後に挙げた2個の基が完全または部分的にハロゲン化されていてもよく、お よび/または1個〜3個の以下の基、すなわちニトロ、シアノ、C1−C4アルキ ル、C1 −C4ハロアルキル、C1−C4アルコキシまたはC1−C4ハロアルコキシを有し てもよく、或いは R4およびR5が共同で、C1−C4アルキルによりモノ置換ないしテトラ置換さ れてもよく、および/または酸素により、またはC1−C4アルキル置換されてい てもよい窒素により中断されてもよいC2−C6アルカンジイル鎖を形成するか、 または R4およびR5が対応の炭素原子と共にカルボニルまたはチオカルボニル基を形 成し、 R6が水素、C1−C4アルキル、C1−C4ハロアルキル、C1−C4アルコキシ 、C1−C4アルコキシ−C2−C4アルコキシ、C1−C4ハロアルコキシ、C3− C6アルケニルオキシ、C3−C6アルキニルオキシまたはNR7R8、 R7が水素またはC1−C4アルキル、 R8がC1−C4アルキル、 XがO、S、NR9、COまたはCR10R11、 YがO、S、NR12、COまたはCR13R14、 R9、R12が水素またはC1−C4アルキル、 R10、R11、R13、R14が水素、C1−C4アルキル、C1−C4ハロアルキル、 C1−C4アルコキシカルボニル、C1−C4ハロアルコキシカルボニルまたはCO NR7R8をそれぞれ意味し、或いは R4およびR9、またはR4およびR10、またはR5およびR12、またはR5およ びR13が共同で、C1−C4アルキルによりモノ置換ないしテトラ置換されていて もよく、および/または酸素により、またはC1−C4アルキル置換されていても よい窒素原子により中断されてもよいC2−C6アルカンジイル鎖を形成し、 R15が下式II で表され、 R16がC1−C6アルキル、 ZがHまたはSO2R17、 R17がC1−C4アルキル、C1−C4ハロアルキル、フェニル、または部分的 または完全にハロゲン化され、および/またはニトロ、シアノ、C1−C4アルキ ル、C1−C4ハロアルキル、C1−C4アルコキシもしくはC1−C4ハロアルコキ シのうちの1〜3個の基を有するフェニル、 R18が水素またはC1−C6アルキルを意味し、4位で結合するピラゾールを 意味し、 XおよびYが同時に硫黄を意味することはない、3−ヘテロシクリル置換ベン ゾイル誘導体であって、 4−[2−クロロ−3−(4,5−ジヒドロイソオキサゾール−3−イル)− 4−メチルスルホニルベンゾイル]−1−エチル−5−ヒドロキシ−1H−ピラ ゾール、4−[2−クロロ−3−(4,5−ジヒドロイソオキサゾール−3−イ ル)−4−メチルスルホニルベンゾイル]−1,3−ジメチル−5−ヒドロキシ −1H−ピラゾール、4−[2−クロロ−3−(5−シアノ−4,5−ジヒドロ イソオキサゾール−3−イル)−4−メチルスルホニルベンゾイル]−1,3− ジメチル−5−ヒドロキシ−1H−ピラゾール、4−[2−クロロ−3−(4, 5−ジヒドロチアゾール−2−イル)−4−メチルスルホニルベンゾイル]−1 ,3−ジメチル−5−ヒドロキシ−1H−ピラゾール、および4−[2−クロロ −3−(チアゾリン−4,5−ジオン−2−イル)−4−メチルスルホニルベン ゾイル]−1,3−ジメチル−5−ヒドロキシ−1H−ピラゾール以外の3−ヘ テロシクリル置換ベンゾイル誘導体、またはその農業上使用可能な塩。 2.一般式Iで表され、 R1、R2が水素、ニトロ、ハロゲン、シアノ、C1−C6アルキル、C1−C6ハ ロアルキル、C1−C6アルコキシ、C1−C6ハロアルコキシ、C1−C6アルキル チオ、C1−C6ハロアルキルチオ、C1−C6アルキルスルフィニル、C1−C6ハ ロアルキルスルフィニル、C1−C6アルキルスルホニルまたはC1−C6ハロアル キルスルホニル、 R3が水素、ハロゲンまたはC1−C6アルキル、 R4、R5が水素、ハロゲン、シアノ、ニトロ、C1−C4アルキル、C1−C4ア ルコキシ−C1−C4アルキル、ジ(C1−C4アルコキシ)−C1−C4アルキル、 ジ(C1−C4アルキル)−アミノ−C1−C4アルキル、[2,2−ジ(C1−C4 アルキル)−1−ヒドラジノ]−C1−C4アルキル、C1−C6アルキルイミノオ キシ−C1−C4アルキル、C1−C4アルコキシカルボニル−C1−C4アルキル、 C1−C4アルキルチオ−C1−C4アルキル、C1−C4ハロアルキル、C1−C4シ アノアルキル、C3−C8シクロアルキル、C1−C4アルコキシ、C1−C4アルコ キシ−C2−C4アルコキシ、C1−C4ハロアルコキシ、C1−C4アルキルチオ、 C1−C4ハロアルキルチオ、ジ(C1−C4アルキル)アミノ、COR6、フェニ ルまたはベンジルを意味し、最後に挙げた2個の基は完全または部分的にハロゲ ン化されていてもよく、および/または1個〜3個の以下の基、すなわちニトロ 、シアノ、C1−C4アルキル、C1−C4ハロアルキル、C1−C4アルコキシまた はC1−C4ハロアルコキシを有してもよく、或いは R4およびR5が共同で、C1−C4アルキルによりモノ置換ないしテトラ置換さ れてもよく、および/または酸素により、またはC1−C4アルキル置換されてい てもよい窒素により中断されてもよいC2−C6アルカンジイル鎖を形成するか、 または R4およびR5が対応の炭素原子と共にカルボニルまたはチオカルボニル基を形 成し、 R6が、C1−C4アルキル、C1−C4ハロアルキル、C1−C4アルコキシ、C1 −C4アルコキシ−C2−C4アルコキシ、C1−C4ハロアルコキ シ、C3−C6アルケニルオキシ、C3−C6アルキニルオキシまたはNR7R8、 R7が水素またはC1−C4アルキル、 R8がC1−C4アルキル、 XがO、S、NR9、COまたはCR10R11、 YがO、S、NR12、COまたはCR13R14、 R9、R12が水素またはC1−C4アルキル、 R10、R11、R13、R14が水素、C1−C4アルキル、C1−C4ハロアルキル、 C1−C4アルコキシカルボニル、C1−C4ハロアルコキシカルボニルまたはCO NR7R8をそれぞれ意味し、或いは R4およびR9、またはR4およびR10、またはR5およびR12、またはR5およ びR13が共同で、C1−C4アルキルによりモノ置換ないしテトラ置換されていて もよく、および/または酸素により、またはC1−C4アルキル置換されていても よい窒素原子により中断されてもよいC2−C6アルカンジイル鎖を形成し、 R15が下式II で表され、 R16がC1−C6アルキル、 ZがHまたはSO2R17、 R17がC1−C4アルキル、C1−C4ハロアルキル、フェニル、または部分的 または完全にハロゲン化され、および/またはニトロ、シアノ、C1−C4アルキ ル、C1−C4ハロアルキル、C1−C4アルコキシもしくはC1−C4ハロアルコキ シのうちの1〜3個の基を有するフェニル、 R18が水素またはC1−C6アルキルを意味し、4位で結合するピラゾール を意味し、 XおよびYが同時に酸素または硫黄を意味することはない3−ヘテロシクリル 置換ベンゾイル誘導体であって、 4−[2−クロロ−3−(4,5−ジヒドロイソオキサゾール−3−イル)− 4−メチルスルホニルベンゾイル]−1−エチル−5−ヒドロキシ−1H−ピラ ゾール、4−[2−クロロ−3−(4,5−ジヒドロイソオキサゾール−3−イ ル)−4−メチルスルホニルベンゾイル]−1,3−ジメチル−5−ヒドロキシ −1H−ピラゾール、4−[2−クロロ−3−(5−シアノ−4,5−ジヒドロ イソオキサゾール−3−イル)−4−メチルスルホニルベンゾイル]−1,3− ジメチル−5−ヒドロキシ−1H−ピラゾール、4−[2−クロロ−3−(4, 5−ジヒドロチアゾール−2−イル)−4−メチルスルホニルベンゾイル]−1 ,3−ジメチル−5−ヒドロキシ−1H−ピラゾール、および4−[2−クロロ −3−(チアゾリン−4,5−ジオン−2−イル)−4−メチルスルホニルベン ゾイル]−1,3−ジメチル−5−ヒドロキシ−1H−ピラゾール以外の3−ヘ テロシクリル置換ベンゾイル誘導体、またはその農業上使用可能な塩。 3.R3が水素を示すことを特徴とする、請求項1または2に記載の式Iの3− ヘテロシクリル置換ベンゾイル誘導体。 4.R1、R2が、ニトロ、ハロゲン、シアノ、C1−C6アルキル、C1−C6ハロ アルキル、C1−C6アルコキシ、C1−C6ハロアルコキシ、C1−C6アルキルチ オ、C1−C6ハロアルキルチオ、C1−C6アルキルスルフィニル、C1−C6ハロ アルキルスルフィニル、C1−C6アルキルスルホニルまたはC1−C6ハロアルキ ルスルホニルを意味することを特徴とする、請求項1〜3のいずれかに記載の式 Iの3−ヘテロシクリル置換ベンゾイル誘導体。 5. ZがSO2R17を意味することを特徴とする、請求項1〜4のいずれかに 記載の式Iの3−ヘテロシクリル置換ベンゾイル誘導体。 6.Zが水素を意味することを特徴とする、請求項1〜4のいずれかに記載の式 Iの3−ヘテロシクリル置換ベンゾイル誘導体。 7.Xが酸素を、YがCR13R14を意味することを特徴とする、請求項1〜4ま たは6に記載の式Iの3−ヘテロシクリル置換ベンゾイル誘導体。 8.R4が、ハロゲン、ニトロ、C1−C4アルキル、C1−C4アルコキシ−C1− C4アルキル、C1−C4アルコキシカルボニル−C1−C4アルキル、C1−C4ア ルキルチオ−C1−C4アルキル、C1−C4ハロアルキル、C1−C4シアノアルキ ル、C3−C8シクロアルキル、C1−C4アルコキシ、C1−C4アルコキシ−C2 −C4アルコキシ、C1−C4ハロアルコキシ、C1−C4アルキルチオ、C1−C4 ハロアルキルチオ、ジ(C1−C4アルキル)アミノ、COR6、フェニルまたは ベンジルを意味し、最後に挙げた2個の基は完全または部分的にハロゲン化され ていてもよく、および/または1個〜3個の以下の基、すなわちニトロ、シアノ 、C1−C4アルキル、C1−C4ハロアルキル、C1−C4アルコキシまたはC1− C4ハロアルコキシを有してもよく、或いは R5が水素またはC1−C4アルキルを意味するか、或いは R4およびR5が共同で、C1−C4アルキルによりモノ置換ないしテトラ置換さ れてもよく、および/または酸素により、またはC1−C4アルキル置換されてい てもよい窒素により中断されてもよいC2−C6アルカンジイル鎖を形成するか、 または R5およびR13が共同で、C1−C4アルキルによりモノ置換ないしテトラ置換 されていてもよく、および/または酸素により、またはC1−C4アルキル置換さ れていてもよい窒素原子により中断されてもよいC2−C6アルカンジイル鎖を形 成することを特徴とする、請求項1〜4、6、7のいずれかに記載の式Iの3− ヘテロシクリル置換ベンゾイル誘導体。 9.R4がC1−C4アルキル、C1−C4ハロアルキル、C1−C4アルコ キシカルボニル、またはCONR7R8、 R5が水素またはC1−C4アルキルを意味するか、或いは R4およびR5が共同で、C1−C4アルキルによりモノ置換ないしテトラ置換さ れてもよく、および/または酸素により、またはC1−C4アルキル置換されてい てもよい窒素により中断されてもよいC2−C6アルカンジイル鎖を形成するか、 または R5およびR13が共同で、C1−C4アルキルによりモノ置換ないしテトラ置換 されていてもよく、および/または酸素により、またはC1−C4アルキル置換さ れていてもよい窒素原子により中断されてもよいC2−C6アルカンジイル鎖を形 成することを特徴とする、請求項1〜4、6〜8のいずれかに記載の式Iの3− ヘテロシクリル置換ベンゾイル誘導体。 10. R4およびR5が水素を意味することを特徴とする、請求項1〜4、6、 7のいずれかに記載の式Iの3−ヘテロシクリル置換ベンゾイル誘導体。 11. R18が水素を意味することを特徴とする、請求項1〜4、6、7、10 のいずれかに記載の式Iの3−ヘテロシクリル置換ベンゾイル誘導体。 12. 4−[2−クロロ−3−(4,5−ジヒドロイソオキサゾール−3−イ ル)−4−メチルスルホニルベンゾイル]−1−メチル−5−ヒドロキシ−1H −ピラゾール。 13. 4−[2−クロロ−3−(4,5−ジヒドロイソオキサゾール−3−イ ル)−4−メチルスルホニルベンゾイル]−1−メチル−5−ヒドロキシ−1H −ピラゾールの農業上有用な塩。 14. XがS、NR9、COまたはCR10R11を意味するか、或いは YがO、S、NR12またはCOを意味することを特徴とする、請求項1〜4、 6のいずれかに記載の式Iの3−ヘテロシクリル置換ベンゾイル誘導体。 15. R18が水素を意味することを特徴とする、請求項1〜4、6、14のい ずれかに記載の式Iの3−ヘテロシクリル置換ベンゾイル誘導体。 16. R4がハロゲン、シアノ、ニトロ、C1−C4アルキル、C1−C4アルコ キシ−C1−C4アルキル、C1−C4アルコキシカルボニル−C1−C4アルキル、 C1−C4アルキルチオ−C1−C4アルキル、C1−C4ハロアルキル、C1−C4シ アノアルキル、C3−C8シクロアルキル、C1−C4アルコキシ、C1−C4アルコ キシ−C2−C4アルコキシ、C1−C4ハロアルコキシ、C1−C4アルキルチオ、 C1−C4ハロアルキルチオ、ジ(C1−C4アルキル)アミノ、COR6、フェニ ルまたはベンジルを意味し、最後に挙げた2個の基は完全または部分的にハロゲ ン化されていてもよく、および/または1個〜3個の以下の基、すなわちニトロ 、シアノ、C1−C4アルキル、C1−C4ハロアルキル、C1−C4アルコキシまた はC1−C4ハロアルコキシを有してもよく、 R5が水素またはC1−C4アルキルを意味するか、または R4およびR5が共同で、C1−C4アルキルによりモノ置換ないしテトラ置換さ れてもよく、および/または酸素により、またはC1−C4アルキル置換されてい てもよい窒素により中断されてもよいC2−C6アルカンジイル鎖を形成するか、 または R4およびR9、またはR4およびR10、またはR5およびR12、またはR5およ びR13が共同で、C1−C4アルキルによりモノ置換ないしテトラ置換されてもよ く、および/または酸素により、またはC1−C4アルキル置換されていてもよい 窒素により中断されてもよいC2−C6アルカンジイル鎖を形成し、 R18がC1−C6アルキルを意味することを特徴とする、請求項1〜4、6、1 4のいずれかに記載の式Iの3−ヘテロシクリル置換ベンゾイル誘導体。 17. 式IIで表され、式中Z=H、R16およびR18が請求項1における定義 と同様の意味を有するピラゾール を、活性化カルボン酸IIIαまたはカルボン酸IIIβ (上記式中R1〜R5、XおよびYは請求項1と同様の意味を有し、L1は求核的 に着脱可能な脱離基を意味する)でアシル化し、得られたアシル化生成物を触媒 の存在下または不存在下に転位反応に付し、生成物Iを得(Z=H)、必要に応 じて、式Iの、Z=SO2R17を意味する場合の3−ヘテロシクリル置換ベンゾ イル誘導体を得るために、前記生成物を、下式V で表され、式中R17が請求項1と同様の意味を有し、L2が求核的に着脱可能な 脱離基を意味する化合物と反応させることを特徴とする、請求項1に記載の式I の3−ヘテロシクリル置換ベンゾイル誘導体の製造法。 18.式IIIで表され、式中 R19がヒドロキシルまたは加水分解により除去可能な基を意味し、 R1〜R5、XおよびYが請求項1〜16において定義された意味を有する、 2−クロロ−3−(4,5−ジヒドロイソオキサゾール−3−イル)−4−メ チルスルホニル安息香酸メチル、2−クロロ−3−(4,5−ジヒドロオキサゾ ール−2−イル)−4−メチルスルホニル安息香酸メチル、および2,4−ジク ロロ−3−(5−メチルカルボニルオキシ−4,5−ジヒドロイソオキサゾール −3−イル)安息香酸メチル以外の、3−ヘテロシクリル置換安息香酸誘導体。 19. R1〜R5、XおよびYが請求項2〜16により定義された意味を有する 、請求項18に記載の式IIIの3−ヘテロシクリル置換安息香酸誘導体。 20.R19がハロゲン、ヒドロキシルまたはC1−C6アルコキシを意味すること を特徴とする、請求項18または19に記載の式IIIの3−ヘテロシクリル置 換安息香酸誘導体。 21. 除草有効量の、請求項1〜16のいずれかに記載の少なくとも1種類の 式Iの3−ヘテロシクリル置換ベンゾイル誘導体またはIの農業上有用な塩と、 農作物保護剤の調製に慣用の助剤とを含む組成物。 22. 除草有効量の、請求項1〜16のいずれかに記載の少なくとも1種類の 式Iの3−ヘテロシクリル置換ベンゾイル誘導体またはIの農業上有用な塩と、 農作物保護剤の調製に慣用の助剤とを混合することを特徴とする、請求項21に 記載の組成物の製造法。 23. 除草有効量の、請求項1〜16のいずれかに記載の少なくとも1種類の 式Iの3−ヘテロシクリル置換ベンゾイル誘導体またはIの農業上有用な塩を、 植物、その生息環境、および/または種子に作用させることを特徴とする、望ま しくない植生の制御方法。 24. 請求項1〜16のいずれかに記載の3−ヘテロシクリル置換ベンゾイル 誘導体またはその農業上有用な塩の、除草剤としての使用法。
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002538188A (ja) * | 1999-03-05 | 2002-11-12 | ビーエーエスエフ アクチェンゲゼルシャフト | 3−複素環置換されたベンゾイル誘導体および補助剤を含有する除草剤混合物 |
JP2009263395A (ja) * | 1997-10-30 | 2009-11-12 | Nippon Soda Co Ltd | 新規なベンゾイルピラゾール化合物及び除草剤 |
WO2013137398A1 (ja) | 2012-03-16 | 2013-09-19 | 日本ゼオン株式会社 | 開環メタセシス重合体水素化物の製造方法及び樹脂組成物 |
Families Citing this family (72)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TR199901667T2 (xx) * | 1997-01-17 | 1999-10-21 | Basf Aktiengesellschaft | 3-Heterosiklil-ikame edilmi� benzoil t�revleri |
WO1999054328A1 (fr) * | 1998-04-22 | 1999-10-28 | Nippon Soda Co., Ltd. | Nouveau composes de benzoylpyrazole et herbicide |
DE19852095A1 (de) * | 1998-11-12 | 2000-05-18 | Basf Ag | Verfahren zur Herstellung von 2-Alkyl-3-(4,5-dihydroisoxazol-3-yl)-acylbenzolen |
EA009301B1 (ru) * | 1998-05-11 | 2007-12-28 | Басф Акциенгезельшафт | Способ получения производных тиоэфиров и его применение |
TR200003752T2 (tr) | 1998-06-16 | 2001-06-21 | Basf Aktiengesellschaft | Sinerjik etkili herbisit karışımlar |
DE59906974D1 (de) * | 1998-12-04 | 2003-10-16 | Basf Ag | 3-(heterocyclyl)-substituierte benzoylpyrazole |
SK7482001A3 (en) | 1998-12-04 | 2001-12-03 | Basf Ag | 3-(heterocyclyl)-benzoylpyrazole-derivatives |
DE19914140A1 (de) * | 1999-03-27 | 2000-09-28 | Bayer Ag | Substituierte Benzoylpyrazole |
AU3329800A (en) * | 1999-03-29 | 2000-10-16 | Nippon Soda Co., Ltd. | Process for the preparation of (e)-3-(1-propenyl)isoxazoline |
EP1174409A4 (en) * | 1999-04-28 | 2003-05-02 | Nippon Soda Co | NOVEL BICYCLOHEPTENE DERIVATIVES AND THEIR PREPARATION PROCESS |
AR024845A1 (es) | 1999-08-06 | 2002-10-30 | Basf Ag | Derivados de 1-cicloalquilpirazolil-benzoilo y sus sales, procedimiento para obtener dichos derivados, las composiciones herbicidas que los contienen y supreparacion, el procedimiento para controlar el crecimiento de plantas indeseadas con dichos derivados y el uso de dichos derivados como herbicida |
DE19946853A1 (de) | 1999-09-30 | 2001-04-05 | Bayer Ag | Substituierte Arylketone |
HUP0204356A3 (en) * | 1999-12-02 | 2004-12-28 | Basf Ag | Herbicidal cyclopropyl-anellated 3-(4,5-dihydroisoxazol-3-yl)-substituted benzoylpyrazole-derivatives, preparation and use thereof and the novel intermediates |
US6613719B1 (en) * | 1999-12-02 | 2003-09-02 | Basf Aktiengesellschaft | 3-(4,5-dihydroisoxazol-3-yl)-substituted benzoylpyrazoles |
MXPA02004860A (es) * | 1999-12-22 | 2003-10-14 | Basf Ag | 3-(4,5-dihdroisoxazol-5-il) benzoilpirazoles. |
CN1509285A (zh) | 2000-01-17 | 2004-06-30 | 被取代的芳基酮类 | |
US6388135B1 (en) | 2000-06-30 | 2002-05-14 | Basf Aktiengesellschaft | Preparation of 4-bromoaniline derivatives |
DK1301469T3 (da) | 2000-07-17 | 2006-10-23 | Basf Ag | Fremstilling af 4-thioalkylbrombenzenderivater |
CA2444723C (en) | 2001-04-27 | 2010-09-28 | Syngenta Participations Ag | Herbicidal composition |
DE10136449A1 (de) * | 2001-05-09 | 2002-11-14 | Bayer Ag | Substituierte Arylketone |
MXPA03010120A (es) | 2001-05-09 | 2004-03-10 | Bayer Cropscience Ag | Arilcetonas substituidas. |
DE10138577A1 (de) * | 2001-05-21 | 2002-11-28 | Bayer Ag | Substituierte Benzoylpyrazole |
DE10142334A1 (de) * | 2001-08-30 | 2003-03-20 | Bayer Cropscience Ag | Herbizide auf Basis von substituierten Arylketonen |
DE10142333A1 (de) * | 2001-08-30 | 2003-03-20 | Bayer Cropscience Ag | Herbizide Mischungen auf Basis von substituierten Arylketonen |
DE10142336A1 (de) | 2001-08-30 | 2003-03-20 | Bayer Cropscience Ag | Selektive Herbizide enthaltend ein Tetrazolinon-Derivat |
DE10146591A1 (de) * | 2001-09-21 | 2003-04-10 | Bayer Cropscience Ag | Herbizide auf Basis von substituierten Thien-3-yl-sulfonylamino(thio)carbonyl-triazolin(thi)onen |
DE10206792A1 (de) | 2002-02-19 | 2003-08-28 | Bayer Cropscience Ag | Substituierte Arylketone |
DE10209645A1 (de) * | 2002-03-05 | 2003-09-18 | Bayer Cropscience Ag | Substituierte Arylketone |
EP1496745B1 (de) * | 2002-04-10 | 2011-01-26 | Basf Se | Verfahren zur erhöhung der widerstandskraft von pflanzen gegen die phytotoxizität von agrochemikalien |
AU2003276043A1 (en) | 2002-06-17 | 2003-12-31 | Merck & Co., Inc. | 1-((5-aryl-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylates and 1-((5-aryl-1,2,4-oxadiazol-3-yl)benzyl)pyrrolidine-3-carboxylates as edg receptor agonists |
KR101006675B1 (ko) * | 2002-07-22 | 2011-01-10 | 바스프 에스이 | 상승작용적 제초제 혼합물 |
EP1917857A1 (en) | 2002-07-24 | 2008-05-07 | Basf Se | Synergistically acting herbicidal mixtures |
DE602004002099T2 (de) * | 2003-03-13 | 2006-12-21 | Basf Ag | Herbizide zusammensetzung, die einen safener enthält |
DE102004010813A1 (de) | 2004-03-05 | 2005-11-10 | Bayer Cropscience Ag | Neue Herbizide auf Basis von substituierten Thien-3-yl-sulfonylamino(thio)carbonyltriazolin(thi)onen und 4-HPPD-Hemmstoffen |
US20070060478A1 (en) | 2005-09-13 | 2007-03-15 | Basf Aktiengesellschaft | Herbicidal mixtures comprising a safener |
US20070123426A1 (en) * | 2005-11-25 | 2007-05-31 | Basf Aktiengesellschaft | Mixtures |
AR056889A1 (es) | 2005-12-15 | 2007-10-31 | Ishihara Sangyo Kaisha | Compuestos benzoilpirazol y herbicidas que los contienen |
BRPI0714656A2 (pt) | 2006-08-04 | 2013-05-07 | Basf Se | concentrado de composto ativo, uso de um concentrado de composto ativo, e, processo para combater vegetaÇço indesejada |
UA89599C2 (uk) * | 2006-08-04 | 2010-02-10 | Басф Се | Водний концентрат діючої речовини з гербіцидною дією та спосіб боротьби з небажаним ростом рослин |
US20100075853A1 (en) | 2006-11-27 | 2010-03-25 | Basf Se | Herbicidally active composition containing a monovalent salt of 4-[2-methyl-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoyl]-1-methyl-5-hydroxy-1h-pyrazole |
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DE102008037628A1 (de) | 2008-08-14 | 2010-02-18 | Bayer Crop Science Ag | Herbizid-Kombination mit Dimethoxytriazinyl-substituierten Difluormethansulfonylaniliden |
WO2011067184A1 (de) | 2009-12-01 | 2011-06-09 | Basf Se | 3- (4, 5 -dihydroisoxazol- 5 -yl) benzoylpyrazolverbindungen und ihre mischungen mit safenern |
AR088857A1 (es) | 2011-11-14 | 2014-07-10 | Basf Se | Compuestos de 1,2,5-oxadiazol sustituido y su uso como herbicidas |
CN104507925A (zh) | 2012-04-27 | 2015-04-08 | 巴斯夫欧洲公司 | 取代的n-(四唑-5-基)-和n-(三唑-5-基)吡啶-3-基羧酰胺化合物及其作为除草剂的用途 |
ES2694200T3 (es) | 2012-04-27 | 2018-12-19 | Basf Se | Compuestos de N-(tetrazol-5-il) y N-(triazol-5-il)arilcarboxamida sustituidos y su uso como herbicidas |
AU2014267561B2 (en) | 2013-05-15 | 2018-06-07 | Basf Se | Substituted N-(tetrazol-5-yl)- and N-(triazol-5-yl)arylcarboxamide compounds and their use as herbicides |
WO2014184058A1 (en) | 2013-05-15 | 2014-11-20 | Basf Se | Substituted 1,2,5-oxadiazole compounds and their use as herbicides |
WO2015007564A1 (en) | 2013-07-18 | 2015-01-22 | Basf Se | Substituted n-(1,2,4-triazol-3-yl)arylcarboxamide compounds and their use as herbicides |
WO2015052178A1 (en) | 2013-10-10 | 2015-04-16 | Basf Se | 1,2,5-oxadiazole compounds and their use as herbicides |
WO2015052173A1 (en) | 2013-10-10 | 2015-04-16 | Basf Se | Tetrazole and triazole compounds and their use as herbicides |
EP2907807A1 (en) | 2014-02-18 | 2015-08-19 | Basf Se | Benzamide compounds and their use as herbicides |
CN105557708B (zh) * | 2014-10-16 | 2018-05-15 | 江苏龙灯化学有限公司 | 一种除草组合物 |
CN104876920A (zh) * | 2015-05-06 | 2015-09-02 | 河南大学 | 异噁唑类化合物、中间体及其制备方法和应用 |
EP3331870B1 (de) * | 2015-08-07 | 2021-06-16 | Bayer CropScience Aktiengesellschaft | 2-(het)aryl-substituierte kondensierte heterocyclen-derivate als schädlingsbekämpfungsmittel |
MX2018007418A (es) | 2015-12-17 | 2018-08-15 | Basf Se | Compuestos de benzamida y sus usos como herbicidas. |
CN108203415A (zh) * | 2016-12-20 | 2018-06-26 | 海利尔药业集团股份有限公司 | 一种制备苯吡唑草酮的方法 |
WO2018219936A1 (en) | 2017-05-30 | 2018-12-06 | Basf Se | Benzamide compounds and their use as herbicides ii |
EP3630734A1 (en) | 2017-05-30 | 2020-04-08 | Basf Se | Benzamide compounds and their use as herbicides |
AR112112A1 (es) | 2017-06-20 | 2019-09-18 | Basf Se | Compuestos de benzamida y su uso como herbicidas |
WO2019016385A1 (en) | 2017-07-21 | 2019-01-24 | Basf Se | BENZAMIDE COMPOUNDS AND THEIR USE AS HERBICIDES |
EP3728243A1 (en) * | 2017-12-22 | 2020-10-28 | Bayer Aktiengesellschaft | Hydroxyisoxazolines and derivatives thereof |
WO2019122345A1 (en) | 2017-12-22 | 2019-06-27 | Basf Se | Benzamide compounds and their use as herbicides |
WO2019162308A1 (en) | 2018-02-21 | 2019-08-29 | Basf Se | Benzamide compounds and their use as herbicides |
WO2019162309A1 (en) | 2018-02-21 | 2019-08-29 | Basf Se | Benzamide compounds and their use as herbicides |
CA3109998A1 (en) | 2018-08-27 | 2020-03-05 | Basf Se | Aqueous compositions of topramezone |
CN112839513A (zh) | 2018-10-03 | 2021-05-25 | 巴斯夫欧洲公司 | 苯唑草酮微乳液组合物 |
WO2020152200A1 (en) | 2019-01-25 | 2020-07-30 | Basf Se | Process for preparation of heteroarylketones |
CN110105349A (zh) * | 2019-04-29 | 2019-08-09 | 河北科技大学 | 苯唑草酮杂质的合成方法及其应用 |
CN117486870B (zh) * | 2023-11-03 | 2024-05-24 | 山东德浩化学有限公司 | 苯唑草酮衍生物及其用途 |
Family Cites Families (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5436648B2 (ja) * | 1974-03-28 | 1979-11-10 | ||
US4070536A (en) | 1975-06-19 | 1978-01-24 | Sankyo Company Limited | Process for the preparation of 4-benzoylpyrazole derivatives |
US4744815A (en) * | 1985-05-11 | 1988-05-17 | Nissan Chemical Industries, Ltd. | 4-benzoyl-1-alkyl (alkenyl) - pyrazoles, composition containing them, herbicidal method of using them, and intermediate in their preparation |
US5175299A (en) * | 1987-03-17 | 1992-12-29 | Nissan Chemical Industries, Ltd. | Benzoic acid derivatives useful as intermediates for the preparation of herbicidal 4-benzoylpyrazoles |
IL85659A (en) | 1987-03-17 | 1992-03-29 | Nissan Chemical Ind Ltd | 4-benzoylpyrazole derivatives,method for their preparation and herbicidal compositions containing them |
US4986845A (en) * | 1988-07-15 | 1991-01-22 | Nissan Chemical Industries Ltd. | Pyrazole derivatives and herbicides containing them |
JP3505195B2 (ja) * | 1992-07-09 | 2004-03-08 | バイエルクロップサイエンス株式会社 | テトラゾリノン類の水田用除草剤としての利用 |
CZ293254B6 (cs) * | 1995-02-24 | 2004-03-17 | Basf Aktiengesellschaft | Pyrazolylbenzoylový derivát, způsob jeho přípravy, herbicidní prostředek s jeho obsahem a způsob potírání nežádoucích rostlin |
AU2405897A (en) | 1996-04-26 | 1997-11-19 | Nippon Soda Co., Ltd. | Novel heterocycle-substituted benzene derivatives and herbicides |
AU3297397A (en) | 1996-06-06 | 1998-01-05 | E.I. Du Pont De Nemours And Company | Herbicidal pyridinyl and pyrazolylphenyl ketones |
US6165944A (en) * | 1997-01-17 | 2000-12-26 | Basf Aktiengesellschaft | 4-(3-heterocyclyl-1-benzoyl) pyrazoles and their use as herbicides |
TR199901667T2 (xx) * | 1997-01-17 | 1999-10-21 | Basf Aktiengesellschaft | 3-Heterosiklil-ikame edilmi� benzoil t�revleri |
JP4441003B2 (ja) | 1997-10-30 | 2010-03-31 | 日本曹達株式会社 | トウモロコシ用除草剤 |
EA009301B1 (ru) * | 1998-05-11 | 2007-12-28 | Басф Акциенгезельшафт | Способ получения производных тиоэфиров и его применение |
DE19852095A1 (de) * | 1998-11-12 | 2000-05-18 | Basf Ag | Verfahren zur Herstellung von 2-Alkyl-3-(4,5-dihydroisoxazol-3-yl)-acylbenzolen |
WO1999063823A1 (de) * | 1998-06-09 | 1999-12-16 | Basf Aktiengesellschaft | Herbizide mischung, enthaltend ein 3 heterocyclyl-substituiertes benzoylderivat |
SK7482001A3 (en) * | 1998-12-04 | 2001-12-03 | Basf Ag | 3-(heterocyclyl)-benzoylpyrazole-derivatives |
DE59906974D1 (de) * | 1998-12-04 | 2003-10-16 | Basf Ag | 3-(heterocyclyl)-substituierte benzoylpyrazole |
AR024845A1 (es) * | 1999-08-06 | 2002-10-30 | Basf Ag | Derivados de 1-cicloalquilpirazolil-benzoilo y sus sales, procedimiento para obtener dichos derivados, las composiciones herbicidas que los contienen y supreparacion, el procedimiento para controlar el crecimiento de plantas indeseadas con dichos derivados y el uso de dichos derivados como herbicida |
US6613719B1 (en) * | 1999-12-02 | 2003-09-02 | Basf Aktiengesellschaft | 3-(4,5-dihydroisoxazol-3-yl)-substituted benzoylpyrazoles |
MXPA02004860A (es) * | 1999-12-22 | 2003-10-14 | Basf Ag | 3-(4,5-dihdroisoxazol-5-il) benzoilpirazoles. |
-
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JP2009263395A (ja) * | 1997-10-30 | 2009-11-12 | Nippon Soda Co Ltd | 新規なベンゾイルピラゾール化合物及び除草剤 |
JP2002538188A (ja) * | 1999-03-05 | 2002-11-12 | ビーエーエスエフ アクチェンゲゼルシャフト | 3−複素環置換されたベンゾイル誘導体および補助剤を含有する除草剤混合物 |
JP4731693B2 (ja) * | 1999-03-05 | 2011-07-27 | ビーエーエスエフ ソシエタス・ヨーロピア | 3−複素環置換されたベンゾイル誘導体および補助剤を含有する除草剤混合物 |
WO2013137398A1 (ja) | 2012-03-16 | 2013-09-19 | 日本ゼオン株式会社 | 開環メタセシス重合体水素化物の製造方法及び樹脂組成物 |
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