AU652500B2 - Substituted indolinones useful as herbicidal agents - Google Patents
Substituted indolinones useful as herbicidal agents Download PDFInfo
- Publication number
- AU652500B2 AU652500B2 AU30464/92A AU3046492A AU652500B2 AU 652500 B2 AU652500 B2 AU 652500B2 AU 30464/92 A AU30464/92 A AU 30464/92A AU 3046492 A AU3046492 A AU 3046492A AU 652500 B2 AU652500 B2 AU 652500B2
- Authority
- AU
- Australia
- Prior art keywords
- cyclohexene
- indolin
- cyclopropane
- optionally substituted
- alkylthio
- 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.)
- Ceased
Links
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical class C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 title claims description 16
- 239000004009 herbicide Substances 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 51
- 241000196324 Embryophyta Species 0.000 claims description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- -1 amino, carboxy Chemical group 0.000 claims description 21
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 239000002689 soil Substances 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000004414 alkyl thio group Chemical group 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 14
- 235000007164 Oryza sativa Nutrition 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 235000009566 rice Nutrition 0.000 claims description 12
- 230000002363 herbicidal effect Effects 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 150000002367 halogens Chemical group 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 210000000056 organ Anatomy 0.000 claims description 6
- 230000001902 propagating effect Effects 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 4
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- LBBWIBWOPGDMAJ-UHFFFAOYSA-N spiro[1h-indole-3,1'-cyclopropane]-2-one Chemical compound O=C1NC2=CC=CC=C2C11CC1 LBBWIBWOPGDMAJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 241000209094 Oryza Species 0.000 claims 2
- QRBITCZXNIJCEA-UHFFFAOYSA-N 2-(1'-acetyl-5'-fluoro-2'-oxospiro[cyclopropane-1,3'-indole]-6'-yl)-4,5,6,7-tetrahydroisoindole-1,3-dione Chemical compound C12=CC(F)=C(N3C(C4=C(CCCC4)C3=O)=O)C=C2N(C(=O)C)C(=O)C21CC2 QRBITCZXNIJCEA-UHFFFAOYSA-N 0.000 claims 1
- RSRIOVYBCPYHCB-UHFFFAOYSA-N 2-(5-fluoro-2-oxospiro[1h-indole-3,1'-cyclopropane]-6-yl)-4,5,6,7-tetrahydroisoindole-1,3-dione Chemical compound C1=C(N2C(C3=C(CCCC3)C2=O)=O)C(F)=CC2=C1NC(=O)C21CC1 RSRIOVYBCPYHCB-UHFFFAOYSA-N 0.000 claims 1
- AFJWMGOTLUUGHF-UHFFFAOYSA-N 4,5,6,7-tetrahydroisoindole-1,3-dione Chemical compound C1CCCC2=C1C(=O)NC2=O AFJWMGOTLUUGHF-UHFFFAOYSA-N 0.000 claims 1
- CCAQCUJAADGTGQ-UHFFFAOYSA-N 4-[2-(methylamino)propyl]aniline Chemical compound CNC(C)CC1=CC=C(N)C=C1 CCAQCUJAADGTGQ-UHFFFAOYSA-N 0.000 claims 1
- VLXPZANTCYAKAR-UHFFFAOYSA-N O=C1NC2=CC(=CC=C2C12CC2)N2C(=O)C1=C(CCCC1)C2=O Chemical compound O=C1NC2=CC(=CC=C2C12CC2)N2C(=O)C1=C(CCCC1)C2=O VLXPZANTCYAKAR-UHFFFAOYSA-N 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 27
- 239000007787 solid Substances 0.000 description 25
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 240000007594 Oryza sativa Species 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 238000010992 reflux Methods 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 235000002096 Vicia faba var. equina Nutrition 0.000 description 9
- 240000008042 Zea mays Species 0.000 description 9
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 9
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 9
- 235000005822 corn Nutrition 0.000 description 9
- 235000005489 dwarf bean Nutrition 0.000 description 9
- 244000013123 dwarf bean Species 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 229910000104 sodium hydride Inorganic materials 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 230000003595 spectral effect Effects 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 125000003003 spiro group Chemical group 0.000 description 5
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 241000209140 Triticum Species 0.000 description 4
- 235000021307 Triticum Nutrition 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000000460 chlorine Chemical group 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 244000058871 Echinochloa crus-galli Species 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- MIELFXNMMLEQCI-UHFFFAOYSA-N 2-(2-fluoro-5-nitrophenyl)-4,5,6,7-tetrahydroisoindole-1,3-dione Chemical compound [O-][N+](=O)C1=CC=C(F)C(N2C(C3=C(CCCC3)C2=O)=O)=C1 MIELFXNMMLEQCI-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- OCOCBVKMMMIDLI-UHFFFAOYSA-N 6-amino-1,3-dihydroindol-2-one Chemical compound NC1=CC=C2CC(=O)NC2=C1 OCOCBVKMMMIDLI-UHFFFAOYSA-N 0.000 description 2
- 244000036975 Ambrosia artemisiifolia Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 230000009418 agronomic effect Effects 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- GLXVIYXAYZPDSM-UHFFFAOYSA-N ethyl 2-(2,4-dinitrophenyl)acetate Chemical group CCOC(=O)CC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O GLXVIYXAYZPDSM-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 208000014674 injury Diseases 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- GXQXQJUREOKWIW-UHFFFAOYSA-N methyl 2-(5-fluoro-2,4-dinitrophenyl)acetate Chemical compound COC(=O)CC1=CC(F)=C([N+]([O-])=O)C=C1[N+]([O-])=O GXQXQJUREOKWIW-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- HNTYWRJULQTORS-UHFFFAOYSA-N 1-benzyl-3-methylpiperazine-2,5-dione Chemical compound O=C1C(C)NC(=O)CN1CC1=CC=CC=C1 HNTYWRJULQTORS-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- KCNISYPADDTFDO-UHFFFAOYSA-N 2,4-dinitrophenylacetic acid Chemical compound OC(=O)CC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O KCNISYPADDTFDO-UHFFFAOYSA-N 0.000 description 1
- BIGLHELIVCJCNR-UHFFFAOYSA-N 2-(1-acetyl-5-fluoro-2-oxo-3h-indol-6-yl)-4,5,6,7-tetrahydroisoindole-1,3-dione Chemical compound C1=C2N(C(=O)C)C(=O)CC2=CC(F)=C1N(C1=O)C(=O)C2=C1CCCC2 BIGLHELIVCJCNR-UHFFFAOYSA-N 0.000 description 1
- LKODBUQTNRCAOF-UHFFFAOYSA-N 2-(5-amino-2-fluorophenyl)-4,5,6,7-tetrahydroisoindole-1,3-dione Chemical compound NC1=CC=C(F)C(N2C(C3=C(CCCC3)C2=O)=O)=C1 LKODBUQTNRCAOF-UHFFFAOYSA-N 0.000 description 1
- YXGRYWMASKMIPE-UHFFFAOYSA-N 2-(5-fluoro-2-oxo-1,3-dihydroindol-6-yl)-4,5,6,7-tetrahydroisoindole-1,3-dione Chemical compound FC1=CC=2CC(=O)NC=2C=C1N(C1=O)C(=O)C2=C1CCCC2 YXGRYWMASKMIPE-UHFFFAOYSA-N 0.000 description 1
- JGSIAOZAXBWRFO-UHFFFAOYSA-N 3-methylsulfanyl-1-phenyl-4,5-dihydrobenzo[g]indazole Chemical compound C1CC2=CC=CC=C2C2=C1C(SC)=NN2C1=CC=CC=C1 JGSIAOZAXBWRFO-UHFFFAOYSA-N 0.000 description 1
- ARQRWWOHJBWWKT-UHFFFAOYSA-N 6-amino-5-fluoro-1,3-dihydroindol-2-one Chemical compound C1=C(F)C(N)=CC2=C1CC(=O)N2 ARQRWWOHJBWWKT-UHFFFAOYSA-N 0.000 description 1
- 240000006995 Abutilon theophrasti Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 240000001592 Amaranthus caudatus Species 0.000 description 1
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 1
- 244000237956 Amaranthus retroflexus Species 0.000 description 1
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 1
- 235000004135 Amaranthus viridis Nutrition 0.000 description 1
- 235000003133 Ambrosia artemisiifolia Nutrition 0.000 description 1
- 102220582664 Astrocytic phosphoprotein PEA-15_N14R_mutation Human genes 0.000 description 1
- DPWHUBQOCVVHLP-UHFFFAOYSA-N C1=C2N(C(=O)C)C(=O)CC2=CC=C1N(C1=O)C(=O)C2=C1CCCC2 Chemical group C1=C2N(C(=O)C)C(=O)CC2=CC=C1N(C1=O)C(=O)C2=C1CCCC2 DPWHUBQOCVVHLP-UHFFFAOYSA-N 0.000 description 1
- 241000238154 Carcinus maenas Species 0.000 description 1
- 235000009344 Chenopodium album Nutrition 0.000 description 1
- 235000005484 Chenopodium berlandieri Nutrition 0.000 description 1
- 235000009332 Chenopodium rubrum Nutrition 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 235000017896 Digitaria Nutrition 0.000 description 1
- 241001303487 Digitaria <clam> Species 0.000 description 1
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 1
- 240000003176 Digitaria ciliaris Species 0.000 description 1
- 235000017898 Digitaria ciliaris Nutrition 0.000 description 1
- 235000005476 Digitaria cruciata Nutrition 0.000 description 1
- 235000006830 Digitaria didactyla Nutrition 0.000 description 1
- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 1
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
- 241000192043 Echinochloa Species 0.000 description 1
- 235000014716 Eleusine indica Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 240000001549 Ipomoea eriocarpa Species 0.000 description 1
- 235000005146 Ipomoea eriocarpa Nutrition 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- STECJAGHUSJQJN-USLFZFAMSA-N LSM-4015 Chemical compound C1([C@@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-USLFZFAMSA-N 0.000 description 1
- 101000941448 Lasioglossum laticeps Lasioglossin-2 Proteins 0.000 description 1
- WLLGXSLBOPFWQV-UHFFFAOYSA-N MGK 264 Chemical compound C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 240000003461 Setaria viridis Species 0.000 description 1
- 235000002248 Setaria viridis Nutrition 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 208000006278 hypochromic anemia Diseases 0.000 description 1
- 235000015250 liver sausages Nutrition 0.000 description 1
- 230000036244 malformation Effects 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- XJDQUPFWVIUWNZ-UHFFFAOYSA-N o-ethyl propanethioate Chemical compound CCOC(=S)CC XJDQUPFWVIUWNZ-UHFFFAOYSA-N 0.000 description 1
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
- 238000003359 percent control normalization Methods 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
- A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/815,674 US5252536A (en) | 1991-12-31 | 1991-12-31 | Substituted indolinones useful as herbicidal agents |
| US815674 | 1991-12-31 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU3046492A AU3046492A (en) | 1993-07-08 |
| AU652500B2 true AU652500B2 (en) | 1994-08-25 |
Family
ID=25218482
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU30464/92A Ceased AU652500B2 (en) | 1991-12-31 | 1992-12-30 | Substituted indolinones useful as herbicidal agents |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5252536A (Sortimente) |
| EP (1) | EP0549892A1 (Sortimente) |
| JP (1) | JPH05255246A (Sortimente) |
| AU (1) | AU652500B2 (Sortimente) |
| CA (1) | CA2086359A1 (Sortimente) |
| TW (1) | TW238240B (Sortimente) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5368685A (en) * | 1992-03-24 | 1994-11-29 | Hitachi, Ltd. | Dry etching apparatus and method |
| US5484763A (en) * | 1995-02-10 | 1996-01-16 | American Cyanamid Company | Substituted benzisoxazole and benzisothiazole herbicidal agents |
| US6545089B1 (en) * | 1997-09-04 | 2003-04-08 | General Electric Company | Impact modified carbonnate polymer composition having improved resistance to degradation and improved thermal stability |
| GB0302512D0 (en) * | 2003-02-03 | 2003-03-05 | Arrow Therapeutics Ltd | Compounds |
| GB0328908D0 (en) * | 2003-12-12 | 2004-01-14 | Syngenta Participations Ag | Chemical compounds |
| GB0328907D0 (en) * | 2003-12-12 | 2004-01-14 | Syngenta Participations Ag | Chemical compounds |
| US20060004154A1 (en) * | 2004-07-02 | 2006-01-05 | Derudder James L | Thermoplastic polycarbonate compositions, method of manufacture, and method of use thereof |
| ES2320955B1 (es) | 2007-03-02 | 2010-03-16 | Laboratorios Almirall S.A. | Nuevos derivados de 3-((1,2,4)triazolo(4,3-a)piridin-7-il)benzamida. |
| ES2329639B1 (es) | 2007-04-26 | 2010-09-23 | Laboratorios Almirall S.A. | Nuevos derivados de 4,8-difenilpoliazanaftaleno. |
| EP2108641A1 (en) | 2008-04-11 | 2009-10-14 | Laboratorios Almirall, S.A. | New substituted spiro[cycloalkyl-1,3'-indo]-2'(1'H)-one derivatives and their use as p38 mitogen-activated kinase inhibitors |
| EP2113503A1 (en) | 2008-04-28 | 2009-11-04 | Laboratorios Almirall, S.A. | New substituted indolin-2-one derivatives and their use as p39 mitogen-activated kinase inhibitors |
| CN102267935B (zh) * | 2011-06-14 | 2013-09-11 | 南开大学 | 一类吲哚满二酮衍生物及其制备方法和用途 |
| EA201600304A1 (ru) * | 2013-10-04 | 2016-09-30 | Байер Кропсайенс Акциенгезельшафт | Применение замещенных дигидрооксиндолилсульфонамидов или их солей для повышения толерантности растений к стрессу |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2159361A1 (de) * | 1971-11-30 | 1973-06-14 | Bayer Ag | Nitrofuranderivate, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| AU2356888A (en) * | 1987-10-09 | 1989-04-13 | Schering Aktiengesellschaft | Substituted azoles and azines, processes for their preparation and their use as herbicides |
| US5045105A (en) * | 1989-02-25 | 1991-09-03 | Basf Aktiengesellschaft | Use of derivatives of n-phenyl-3,4,5,6-tetrahydrophthalimide for the desiccation and abscission of plant organs |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4640707A (en) * | 1984-07-23 | 1987-02-03 | Sumitomo Chemical Company, Ltd. | Tetrahydrophthalimides and their herbicidal use |
| CA1326669C (en) * | 1987-01-14 | 1994-02-01 | Shell Canada Limited | Herbicidal oxoindanes and tetrahydronaphthalenes |
| DE3807295A1 (de) * | 1988-03-05 | 1989-09-14 | Basf Ag | Neue n-heteroaryl-tetrahydrophthalimidverbindungen |
| DE3924052A1 (de) * | 1989-07-21 | 1991-01-24 | Bayer Ag | N- (indol-6-yl)-heterocyclen |
| US5076835A (en) * | 1990-05-31 | 1991-12-31 | America Cyanamid Company | Aryloxyspiroalkylindolinone herbicides |
-
1991
- 1991-12-31 US US07/815,674 patent/US5252536A/en not_active Expired - Fee Related
-
1992
- 1992-11-26 EP EP92120159A patent/EP0549892A1/en not_active Withdrawn
- 1992-12-17 TW TW081110138A patent/TW238240B/zh active
- 1992-12-28 JP JP4358800A patent/JPH05255246A/ja active Pending
- 1992-12-29 CA CA002086359A patent/CA2086359A1/en not_active Abandoned
- 1992-12-30 AU AU30464/92A patent/AU652500B2/en not_active Ceased
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2159361A1 (de) * | 1971-11-30 | 1973-06-14 | Bayer Ag | Nitrofuranderivate, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| AU2356888A (en) * | 1987-10-09 | 1989-04-13 | Schering Aktiengesellschaft | Substituted azoles and azines, processes for their preparation and their use as herbicides |
| US5045105A (en) * | 1989-02-25 | 1991-09-03 | Basf Aktiengesellschaft | Use of derivatives of n-phenyl-3,4,5,6-tetrahydrophthalimide for the desiccation and abscission of plant organs |
Also Published As
| Publication number | Publication date |
|---|---|
| AU3046492A (en) | 1993-07-08 |
| JPH05255246A (ja) | 1993-10-05 |
| CA2086359A1 (en) | 1993-07-01 |
| EP0549892A1 (en) | 1993-07-07 |
| US5252536A (en) | 1993-10-12 |
| TW238240B (Sortimente) | 1995-01-11 |
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