JP3897698B2 - 置換アリールケトン類 - Google Patents
置換アリールケトン類 Download PDFInfo
- Publication number
- JP3897698B2 JP3897698B2 JP2002587416A JP2002587416A JP3897698B2 JP 3897698 B2 JP3897698 B2 JP 3897698B2 JP 2002587416 A JP2002587416 A JP 2002587416A JP 2002587416 A JP2002587416 A JP 2002587416A JP 3897698 B2 JP3897698 B2 JP 3897698B2
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- case
- ethyl
- chlorine
- cyano
- 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.)
- Expired - Fee Related
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- -1 Substituted aryl ketones Chemical class 0.000 title description 622
- 150000001875 compounds Chemical class 0.000 claims description 88
- 238000000034 method Methods 0.000 claims description 40
- 239000000203 mixture Substances 0.000 claims description 27
- 230000002363 herbicidal effect Effects 0.000 claims description 5
- 239000004067 bulking agent Substances 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 83
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 68
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 67
- 239000001257 hydrogen Substances 0.000 description 53
- 229910052739 hydrogen Inorganic materials 0.000 description 53
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 39
- 125000004432 carbon atom Chemical group C* 0.000 description 37
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 36
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 33
- 229910052736 halogen Inorganic materials 0.000 description 33
- 150000002367 halogens Chemical group 0.000 description 33
- 150000002431 hydrogen Chemical class 0.000 description 33
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 33
- 125000000217 alkyl group Chemical group 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 239000000460 chlorine Substances 0.000 description 24
- 229910052801 chlorine Inorganic materials 0.000 description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 23
- 125000003545 alkoxy group Chemical group 0.000 description 22
- 125000004414 alkyl thio group Chemical group 0.000 description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 20
- 230000008569 process Effects 0.000 description 20
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 19
- 229910052794 bromium Inorganic materials 0.000 description 19
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 19
- 239000002994 raw material Substances 0.000 description 19
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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 17
- 238000006243 chemical reaction Methods 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N Vilsmeier-Haack reagent Natural products CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 14
- 125000003118 aryl group Chemical group 0.000 description 14
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 125000000547 substituted alkyl group Chemical group 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 240000008042 Zea mays Species 0.000 description 12
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 12
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 12
- 125000000753 cycloalkyl group Chemical group 0.000 description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 12
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 11
- 235000005822 corn Nutrition 0.000 description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 10
- 125000003282 alkyl amino group Chemical group 0.000 description 10
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 10
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 10
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 10
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 239000011737 fluorine Substances 0.000 description 10
- 229910052731 fluorine Inorganic materials 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- 229910052708 sodium Inorganic materials 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
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 9
- 244000038559 crop plants Species 0.000 description 9
- 239000003085 diluting agent Substances 0.000 description 9
- 239000001301 oxygen Substances 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- 239000002689 soil Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 125000004663 dialkyl amino group Chemical group 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 108090000623 proteins and genes Proteins 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 7
- 241000220259 Raphanus Species 0.000 description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 7
- 125000003710 aryl alkyl group Chemical group 0.000 description 7
- 125000004104 aryloxy group Chemical group 0.000 description 7
- 125000000480 butynyl group Chemical class [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000003995 emulsifying agent Substances 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 239000004009 herbicide Substances 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 125000002568 propynyl group Chemical class [*]C#CC([H])([H])[H] 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 235000010469 Glycine max Nutrition 0.000 description 6
- 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 125000003302 alkenyloxy group Chemical group 0.000 description 6
- 125000000304 alkynyl group Chemical group 0.000 description 6
- 125000005133 alkynyloxy group Chemical group 0.000 description 6
- 125000005110 aryl thio group Chemical group 0.000 description 6
- 125000004369 butenyl group Chemical class C(=CCC)* 0.000 description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 6
- 125000004093 cyano group Chemical group *C#N 0.000 description 6
- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 description 6
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 6
- 230000006378 damage Effects 0.000 description 6
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 238000003306 harvesting Methods 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 238000012360 testing method Methods 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
- 244000068988 Glycine max Species 0.000 description 5
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 239000003086 colorant Substances 0.000 description 5
- WQJONRMBVKFKOB-UHFFFAOYSA-N cyanatosulfanyl cyanate Chemical compound N#COSOC#N WQJONRMBVKFKOB-UHFFFAOYSA-N 0.000 description 5
- 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 description 5
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 5
- 235000013399 edible fruits Nutrition 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 125000004368 propenyl group Chemical class C(=CC)* 0.000 description 5
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 description 4
- PVSGXWMWNRGTKE-UHFFFAOYSA-N 5-methyl-2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]pyridine-3-carboxylic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC=C(C)C=C1C(O)=O PVSGXWMWNRGTKE-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 0 Cc1c(*)[n](*)nc1* Chemical compound Cc1c(*)[n](*)nc1* 0.000 description 4
- 239000005562 Glyphosate Substances 0.000 description 4
- 240000007594 Oryza sativa Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 241000209140 Triticum Species 0.000 description 4
- 235000021307 Triticum Nutrition 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 4
- 125000005195 alkyl amino carbonyloxy group Chemical group 0.000 description 4
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 4
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 125000005129 aryl carbonyl group Chemical group 0.000 description 4
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 4
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 4
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 235000011181 potassium carbonates Nutrition 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 4
- JGHCFFKOPIXERS-UHFFFAOYSA-N 2,4-dichloro-3-(2-chloroethoxy)benzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C(OCCCl)=C1Cl JGHCFFKOPIXERS-UHFFFAOYSA-N 0.000 description 3
- IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 description 3
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical class O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- GXGJIOMUZAGVEH-UHFFFAOYSA-N Chamazulene Chemical group CCC1=CC=C(C)C2=CC=C(C)C2=C1 GXGJIOMUZAGVEH-UHFFFAOYSA-N 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 235000002595 Solanum tuberosum Nutrition 0.000 description 3
- 244000061456 Solanum tuberosum Species 0.000 description 3
- 229940100389 Sulfonylurea Drugs 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Chemical class C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000004659 aryl alkyl thio group Chemical group 0.000 description 3
- 125000005199 aryl carbonyloxy group Chemical group 0.000 description 3
- 125000002618 bicyclic heterocycle group Chemical group 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 235000013339 cereals Nutrition 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 230000007123 defense Effects 0.000 description 3
- 239000012024 dehydrating agents Substances 0.000 description 3
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 3
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 3
- 125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 125000002534 ethynyl group Chemical class [H]C#C* 0.000 description 3
- 125000002541 furyl group Chemical group 0.000 description 3
- 229940097068 glyphosate Drugs 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000005981 pentynyl group Chemical class 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 125000000168 pyrrolyl group Chemical group 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 239000010902 straw Substances 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 3
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 3
- 125000000391 vinyl group Chemical class [H]C([*])=C([H])[H] 0.000 description 3
- NYHLMHAKWBUZDY-QMMMGPOBSA-N (2s)-2-[2-chloro-5-[2-chloro-4-(trifluoromethyl)phenoxy]benzoyl]oxypropanoic acid Chemical compound C1=C(Cl)C(C(=O)O[C@@H](C)C(O)=O)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 NYHLMHAKWBUZDY-QMMMGPOBSA-N 0.000 description 2
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-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
- BQZXUHDXIARLEO-UHFFFAOYSA-N tribenuron Chemical compound COC1=NC(C)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 BQZXUHDXIARLEO-UHFFFAOYSA-N 0.000 description 1
- RYVBINGWVJJDPU-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC RYVBINGWVJJDPU-UHFFFAOYSA-M 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
- HNJXPTMEWIVQQM-UHFFFAOYSA-M triethyl(hexadecyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](CC)(CC)CC HNJXPTMEWIVQQM-UHFFFAOYSA-M 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 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
- AKTQJCBOGPBERP-UHFFFAOYSA-N triflusulfuron Chemical compound FC(F)(F)COC1=NC(N(C)C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C(O)=O)=N1 AKTQJCBOGPBERP-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having 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
- 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
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D261/12—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
A1は、単結合を表すか、あるいはO(酸素)、S(硫黄)、SOまたはSO2を表し;
A2は、アルカンジイル(アルキレン)、アルケンジイルまたはアルキンジイルを表し;
Qは、O(酸素)またはS(硫黄)を表し;
R1は、水素を表すか、あるいは各場合で置換されていても良いアルキル、アルコキシ、アルキルチオ、アルキルスルフィニル、アルキルスルホニル、アルキルアミノ、ジアルキルアミノ、アルケニル、アルキニル、シクロアルキル、シクロアルキルアルキル、アリールまたはアリールアルキルを表すか、あるいは−C(Q)−R2の基を表し;
R2は、水素、アミノ、シアノアミノ、ニトロアミノ、ヒドロキシアミノ、ヒドラジノを表すか、あるいは各場合で置換されていても良いアルキル、アルキルカルボニル、アルコキシ、アルコキシカルボニル、アルキルチオ、アルキルアミノ、ジアルキルアミノ、アルコキシアミノ、N−アルキル−アルコキシアミノ、アルキルヒドラジノ、ジアルキルヒドラジノ、アルケニル、アルケニルオキシ、アルケニルアミノ、アルケニルオキシアミノ、アルキニル、アルキニルオキシ、アルキニルアミノ、シクロアルキル、シクロアルキルオキシ、シクロアルキルアミノ、シクロアルキルアルキル、シクロアルキルアルコキシ、シクロアルキルアルキルアミノ、アリール、アリールカルボニル、アリールオキシ、アリールオキシカルボニル、アリールチオ、アリールアミノ、アリールヒドラジノ、アリールアルキル、アリールアルコキシ、アリールアルキルチオ、アリールアルキルアミノ、複素環、複素環オキシ、複素環チオ、複素環アミノ、複素環アルキル、複素環アルコキシ、複素環アルキルチオまたは複素環アルキルアミノを表し;
Xは、水素、ニトロ、シアノ、カルボキシル、カルバモイル、チオカルバモイル、ハロゲンを表すか、あるいは各場合で置換されていても良いアルキル、アルコキシ、アルキルチオ、アルキルスルフィニル、アルキルスルホニル、アルキルアミノ、ジアルキルアミノまたはジアルキルアミノスルホニルを表し;
Yは、水素、ニトロ、シアノ、カルボキシル、カルバモイル、チオカルバモイル、ハロゲンを表すか、あるいは各場合で置換されていても良いアルキル、アルコキシ、アルキルチオ、アルキルスルフィニル、アルキルスルホニル、アルキルアミノ、ジアルキルアミノまたはジアルキルアミノスルホニルを表し;
Zは、下記の基のいずれかを表し;
mは0〜6の数字を表し;
R3は、水素、ハロゲンを表すか、あるいは各場合で置換されていても良いアルキル、アルキルチオまたはアリールを表すか、あるいはmが2を表す場合に、第2の基R3と一体となって、酸素またはアルカンジイル(アルキレン)を表しても良く;
R4は、ヒドロキシル、ホルミルオキシ、ハロゲンを表すか、あるいは各場合で置換されていても良いアルコキシ、アルキルチオ、アルキルスルフィニル、アルキルスルホニル、アルキルカルボニルオキシ、アルコキシカルボニルオキシ、アルキルアミノカルボニルオキシ、アルキルスルホニルオキシ、アルケニルオキシ、アルキニルオキシ、アリールオキシ、アリールチオ、アリールスルフィニル、アリールスルホニル、アリールカルボニルオキシ、アリールカルボニルアルコキシ、アリールスルホニルオキシ、アリールアルコキシ、アリールアルキルチオ、アリールアルキルスルフィニルまたはアリールアルキルスルホニルを表し;
R5は、水素、シアノ、カルバモイル、チオカルバモイル、ハロゲンを表すか、あるいは各場合で置換されていても良いアルキル、アルコキシ、アルキルチオ、アルキルスルフィニル、アルキルスルホニル、アルコキシカルボニルまたはシクロアルキルを表し;
R6は、水素を表すか、あるいは各場合で置換されていても良いアルキル、アルケニル、アルキニル、シクロアルキル、シクロアルキルアルキル、アリールまたはアリールアルキルを表し;
R7は、ヒドロキシル、ホルミルオキシを表すか、あるいは各場合で置換されていても良いアルコキシ、アルキルカルボニルオキシ、アルコキシカルボニルオキシ、アルキルアミノカルボニルオキシ、アルキルスルホニルオキシ、アルケニルオキシ、アルキニルオキシ、アリールアルコキシ、アリールカルボニルオキシ、アリールカルボニルアルコキシまたはアリールスルホニルオキシを表し;
R8は、水素、シアノ、カルバモイル、チオカルバモイル、ハロゲンを表すか、あるいは各場合で置換されていても良いアルキル、アルキルカルボニル、アルコキシ、アルコキシカルボニル、アルキルチオ、アルキルスルフィニルまたはアルキルスルホニルを表し;
R9は、水素を表すか、あるいは各場合で置換されていても良いアルキルまたはシクロアルキルを表し;
R10は、水素を表すか、あるいは各場合で置換されていても良いアルキルまたはシクロアルキルを表し;
R11は、水素、シアノ、カルバモイル、ハロゲンを表すか、あるいは各場合で置換されていても良いアルキル、アルコキシ、アルコキシカルボニル、アルキルチオ、アルキルスルフィニルまたはアルキルスルホニルを表す。
(a)適切であれば1以上の反応補助剤存在下に、そして適切であれば1以上の希釈剤存在下に、下記一般式(II)のアミノ化合物:
QおよびR2は上記で定義の通りであり;
Q1は、ハロゲン、アルコキシ、アルキルチオ、アリールオキシまたはアリールチオを表し;好ましくは塩素、臭素、メトキシ、エトキシ、メチルチオ、エチルチオ、フェニルオキシまたはフェニルチオを表す。]と反応させるか、
または適切であれば、相当するイソ(チオ)シアネートと反応させる場合に;あるいは
(b)適切であれば脱水剤存在下に、そして適切であれば1以上の反応補助剤存在下に、そして適切であれば1以上の希釈剤存在下に、下記一般式(IV)のカルボン酸:
(c)適切であれば1以上の反応補助剤存在下に、そして適切であれば1以上の希釈剤存在下に、下記一般式(Ia)の置換ベンゾイルケトン:
(d)適切であれば1以上の反応補助剤存在下に、そして適切であれば1以上の希釈剤存在下に、下記一般式(VI)のアリールケトン:
A1、A2、Q、R1、X、YおよびZは上記で定義の通りであり;
Q2は、ハロゲン、アルコキシ、アルキルチオ、アリールオキシまたはアリールチオを表し、好ましくは塩素、臭素、メトキシ、エトキシ、メチルチオ、エチルチオ、フェニルオキシまたはフェニルチオを表す。]、
または適切であれば相当するイソ(チオ)シアネートを、下記一般式(VII)の化合物:
本発明による方法(a)、(b)、(c)または(d)を実施した後に、得られた一般式(I)の化合物について、適切であって置換基の定義の範囲内である場合に、一般式(I)の他の化合物への変換を行う通常の方法に従って、後段階反応(例えば、置換、酸化もしくは還元反応)を行う。
A1、A2、X、YおよびZは上記で定義の通りであり;
X1は、ハロゲン(好ましくは、フッ素、塩素、臭素もしくはヨウ素、特には塩素もしくは臭素)を表す。]を、アンモニアまたは下記一般式(IX)のアミノ化合物:
(α)適切であればアセトニトリルもしくはエタノールなどの希釈剤存在下に、0℃〜100℃の温度で、下記一般式(X)のイソ(チオ)シアネート:
A1、A2、Q、XおよびYは上記で定義の通りであり;
Rは、水素、アルカリ金属もしくはアルカリ土類金属等価物(好ましくはナトリウムもしくはカリウム)またはアルキル(好ましくは、C1〜C4−アルキル、特にはメチルまたはエチル)を表す。]を、下記一般式(VII)の化合物:
(β)適切であれば炭酸カリウムもしくはトリエチルアミンなどの1以上の反応補助剤存在下に、適切であればアセトニトリルもしくはN,N−ジメチルホルムアミドなどの1以上の希釈剤存在下に、0℃〜100℃の温度で、下記一般式(XI)のアミノ化合物:
A1、A2、R1、XおよびYは上記で定義の通りであり;
Rは、水素、アルカリ金属もしくはアルカリ土類金属等価物(好ましくはナトリウムもしくはカリウム)またはアルキル(好ましくは、C1〜C4−アルキル、特にはメチルまたはエチル)を表す。]を、下記一般式(III)の(チオ)オキソ化合物:
QおよびR2は上記で定義の通りであり;
Q1は、ハロゲン、アルコキシ、アルキルチオ、アリールオキシまたはアリールチオ、好ましくは塩素、臭素、メトキシ、エトキシ、メチルチオ、エチルチオ、フェニルオキシまたはフェニルチオを表す。]、または
適切であれば、相当するイソ(チオ)シアネートと反応させる場合に得られる。
臭化テトラブチルアンモニウム、塩化テトラブチルアンモニウム、塩化テトラオクチルアンモニウム、硫酸水素テトラブチルアンモニウム、塩化メチル−トリオクチルアンモニウム、塩化ヘキサデシル−トリメチルアンモニウム、臭化ヘキサデシル−トリエチルアンモニウム、塩化ベンジル−トリメチルアンモニウム、塩化ベンジル−トリエチルアンモニウム、水酸化ベンジル−トリメチルアンモニウム、水酸化ベンジル−トリエチルアンモニウム、塩化ベンジル−トリブチルアンモニウム、臭化ベンジル−トリブチルアンモニウム、臭化テトラブチルホスホニウム、塩化テトラブチルホスホニウム、臭化トリブチル−ヘキサデシルホスホニウム、塩化ブチル−トリフェニルホスホニウム、臭化エチル−トリオクチルホスホニウム、臭化テトラフェニルホスホニウムがある。
(実施例1)
[3−(2−アミノエトキシ)−2,4−ジクロロ−フェニル−(1−エチル−5−ヒドロキシ−1H−ピラゾール−4−イル)−メタノン1.0g(2.9mmol)および炭酸カリウム0.8g(5.8mmol)のアセトニトリル(6mL)懸濁液に、塩化アセチル0.28g(3.6mmol)を加え、反応混合物を室温(約20℃)で24時間撹拌する。溶媒を減圧下に除去し、残留物を少量の水に溶かす。得られた水溶液を塩化メチレンで洗浄し、次に塩酸で酸性とし、酢酸エチルで抽出する。有機相を飽和塩化ナトリウム水溶液で洗浄し、硫酸ナトリウムで脱水し、濾過する。濾液から、溶媒を減圧下に注意深く留去する。
[3−(2−アミノ−エトキシ)−2,4−ジクロロ−フェニル−(1−エチル−5−ヒドロキシ−1H−ピラゾール−4−イル)−メタノン0.5g(1.45mmol)のメタノール(10mL)懸濁液に、メチルイソシアネート0.24g(3.3mmol)を加え、反応混合物を24時間還流下に沸騰加熱する。水および酢酸エチルを加え、有機相を分液し、飽和塩化ナトリウム水溶液で洗浄し、硫酸ナトリウムで脱水し、濾過する。濾液から、溶媒を減圧下に注意深く留去する。
最初に、アセトニトリル50mLに、1,3−シクロヘキサンジオン0.7g(6.25mmol)およびN−(3−カルボキシル−2,6−ジクロロ−ベンジル)−N′−イソプロピル−チオ尿素2.0g(6.25mmol)を加える。ジシクロヘキシルカルボジイミド1.5g(7.25mmol)を加え、混合物を室温(約20℃)で15時間撹拌する。トリエチルアミン0.7g(7mmol)および2−ヒドロキシ−2−メチル−プロピオニトリル0.7g(8mmol)を加え、混合物を室温でさらに15時間撹拌する。混合物を1M炭酸カリウム水溶液50mLとともに撹拌し、吸引濾過し、濾液を塩酸を用いるpH4の酸性とする。混合物を塩化メチレン各30mLで3回抽出し、合わせた有機相を硫酸マグネシウムで脱水し、濾過する。溶媒を減圧下に除去する。
1−ブロモ−4−(ブロモメチル)−ベンゼン0.25g(1.0mmol)および1,8−ジアザビシクロ−(5.4.0)−ウンデク−7−エン(DBU)0.15g(0.5mmol)を、N−(2−(2,6−ジクロロ−3−[(1−エチル−5−ヒドロキシ−1H−ピラゾール−4−イル)−カルボニル]−フェノキシ}−エチル)−アセトアミド0.193g(0.5mmol)のトルエン(6mL)溶液に加え、反応混合物を還流沸騰下に9時間加熱する。上清のトルエン相を傾斜法で除去し、残った油状残留物を移動相として塩化メチレン/メタノール(9:1)を用いるカラムクロマトグラフィーによって分離する。
(実施例(II−1))
(実施例(IV−1))
(実施例A)
発芽前試験
溶媒:アセトン5重量部;
乳化剤:アルキルアリールポリグリコールエーテル1重量部。
100%=完全破壊。
発芽後試験
溶媒:アセトン5重量部;
乳化剤:アルキルアリールポリグリコールエーテル1重量部。
100%=完全破壊。
Claims (3)
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DE10136449A DE10136449A1 (de) | 2001-05-09 | 2001-07-26 | Substituierte Arylketone |
PCT/EP2002/004701 WO2002090336A1 (de) | 2001-05-09 | 2002-04-29 | Substituierte arylketone |
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EP (1) | EP1387831A1 (ja) |
JP (2) | JP3897698B2 (ja) |
CN (1) | CN1297543C (ja) |
BR (1) | BR0209537A (ja) |
CA (1) | CA2449187A1 (ja) |
MX (1) | MXPA03010120A (ja) |
PL (1) | PL365734A1 (ja) |
RU (1) | RU2302411C2 (ja) |
WO (1) | WO2002090336A1 (ja) |
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EP1140811B1 (en) * | 1998-12-21 | 2006-08-02 | Syngenta Participations AG | Novel herbicides |
DE10209645A1 (de) * | 2002-03-05 | 2003-09-18 | Bayer Cropscience Ag | Substituierte Arylketone |
US7217732B2 (en) * | 2002-06-19 | 2007-05-15 | Schering Corporation | Cannabinoid receptor agonists |
CA2531068A1 (en) | 2003-07-10 | 2005-01-27 | Achillion Pharmaceuticals, Inc. | Substituted arylthiourea derivatives useful as inhibitors of viral replication |
JP5122799B2 (ja) * | 2005-12-15 | 2013-01-16 | 石原産業株式会社 | ベンゾイルピラゾール系化合物及びそれらを含有する除草剤 |
AR056889A1 (es) * | 2005-12-15 | 2007-10-31 | Ishihara Sangyo Kaisha | Compuestos benzoilpirazol y herbicidas que los contienen |
JP5420169B2 (ja) * | 2006-12-27 | 2014-02-19 | 石原産業株式会社 | ベンゾイルピラゾール系化合物を含有する除草剤 |
JP5890831B2 (ja) * | 2010-07-21 | 2016-03-22 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングBayer Intellectual Property GmbH | (4−ハロゲンアルキル−3−チオベンゾイル)シクロヘキサンジオン類および除草剤としてのそれの使用 |
JP6470897B2 (ja) | 2012-06-29 | 2019-02-13 | 石原産業株式会社 | 除草効力が向上した除草組成物 |
US9950999B2 (en) | 2016-08-12 | 2018-04-24 | International Business Machines Corporation | Non-ionic low diffusing photo-acid generators |
CN112409226B (zh) * | 2019-08-23 | 2024-04-05 | 东莞市东阳光农药研发有限公司 | 取代的苯甲酰类化合物及其应用 |
CN112409263B (zh) * | 2019-08-23 | 2024-04-05 | 东莞市东阳光农药研发有限公司 | 取代的苯甲酰类化合物及其应用 |
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2002
- 2002-04-29 EP EP02730220A patent/EP1387831A1/de not_active Withdrawn
- 2002-04-29 JP JP2002587416A patent/JP3897698B2/ja not_active Expired - Fee Related
- 2002-04-29 US US10/477,031 patent/US7112554B2/en not_active Expired - Fee Related
- 2002-04-29 CN CNB028136853A patent/CN1297543C/zh not_active Expired - Fee Related
- 2002-04-29 WO PCT/EP2002/004701 patent/WO2002090336A1/de active Application Filing
- 2002-04-29 RU RU2003135789/04A patent/RU2302411C2/ru not_active IP Right Cessation
- 2002-04-29 MX MXPA03010120A patent/MXPA03010120A/es active IP Right Grant
- 2002-04-29 PL PL02365734A patent/PL365734A1/xx not_active Application Discontinuation
- 2002-04-29 BR BR0209537-8A patent/BR0209537A/pt not_active IP Right Cessation
- 2002-04-29 CA CA002449187A patent/CA2449187A1/en not_active Abandoned
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2006
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- 2006-10-17 JP JP2006282224A patent/JP2007084549A/ja active Pending
Also Published As
Publication number | Publication date |
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MXPA03010120A (es) | 2004-03-10 |
CN1297543C (zh) | 2007-01-31 |
RU2302411C2 (ru) | 2007-07-10 |
JP2004534028A (ja) | 2004-11-11 |
WO2002090336A1 (de) | 2002-11-14 |
US20040176253A1 (en) | 2004-09-09 |
CN1524075A (zh) | 2004-08-25 |
BR0209537A (pt) | 2004-03-09 |
RU2003135789A (ru) | 2005-05-20 |
US20060252647A1 (en) | 2006-11-09 |
EP1387831A1 (de) | 2004-02-11 |
PL365734A1 (en) | 2005-01-10 |
JP2007084549A (ja) | 2007-04-05 |
US7456133B2 (en) | 2008-11-25 |
CA2449187A1 (en) | 2002-11-14 |
US7112554B2 (en) | 2006-09-26 |
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