IL92341A - 2-) Benzoyl- (2, (3,) (4-trimethyl) (1,3-cyclohexanediones and their use as herbicides - Google Patents
2-) Benzoyl- (2, (3,) (4-trimethyl) (1,3-cyclohexanediones and their use as herbicides Download PDFInfo
- Publication number
- IL92341A IL92341A IL9234189A IL9234189A IL92341A IL 92341 A IL92341 A IL 92341A IL 9234189 A IL9234189 A IL 9234189A IL 9234189 A IL9234189 A IL 9234189A IL 92341 A IL92341 A IL 92341A
- Authority
- IL
- Israel
- Prior art keywords
- hydrogen
- methyl
- alkyl
- bromine
- ethyl
- Prior art date
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- -1 2-(2',3',4'-trisubstituted benzoyl)-1,3-cyclohexanediones Chemical class 0.000 title description 43
- 239000004009 herbicide Substances 0.000 title description 15
- 239000001257 hydrogen Substances 0.000 claims abstract description 133
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 133
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 112
- 150000001875 compounds Chemical class 0.000 claims abstract description 62
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 43
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 35
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 32
- 229910052794 bromium Chemical group 0.000 claims abstract description 32
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 30
- 239000000460 chlorine Substances 0.000 claims abstract description 23
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 23
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000001301 oxygen Substances 0.000 claims abstract description 21
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 21
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 17
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 13
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 8
- 150000002367 halogens Chemical class 0.000 claims abstract description 8
- 229910052717 sulfur Chemical group 0.000 claims abstract description 8
- 239000011593 sulfur Chemical group 0.000 claims abstract description 8
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract description 5
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract 2
- 150000002431 hydrogen Chemical group 0.000 claims description 90
- 239000000203 mixture Substances 0.000 claims description 51
- 125000000217 alkyl group Chemical group 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 40
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- 125000001246 bromo group Chemical group Br* 0.000 claims 15
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 3
- JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical group C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 claims 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 12
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 abstract description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 65
- 238000006243 chemical reaction Methods 0.000 description 64
- 239000003921 oil Substances 0.000 description 58
- 235000019198 oils Nutrition 0.000 description 58
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
- 239000000243 solution Substances 0.000 description 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 31
- 239000002585 base Substances 0.000 description 28
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 23
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 21
- 239000002904 solvent Substances 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- 235000010233 benzoic acid Nutrition 0.000 description 17
- 239000002253 acid Substances 0.000 description 16
- 238000007796 conventional method Methods 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- 241000196324 Embryophyta Species 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000005711 Benzoic acid Substances 0.000 description 13
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 13
- 239000000543 intermediate Substances 0.000 description 13
- 238000012360 testing method Methods 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 12
- 230000000875 corresponding effect Effects 0.000 description 12
- 239000002689 soil Substances 0.000 description 12
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 11
- 230000003197 catalytic effect Effects 0.000 description 11
- 238000009472 formulation Methods 0.000 description 11
- 229910000027 potassium carbonate Inorganic materials 0.000 description 11
- 229940093956 potassium carbonate Drugs 0.000 description 11
- 239000000376 reactant Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 239000007795 chemical reaction product Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000002270 dispersing agent Substances 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 230000007062 hydrolysis Effects 0.000 description 9
- 238000006460 hydrolysis reaction Methods 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 8
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 8
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000004566 IR spectroscopy Methods 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 6
- 238000004949 mass spectrometry Methods 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- XTIGGAHUZJWQMD-UHFFFAOYSA-N 1-chloro-2-methoxyethane Chemical compound COCCCl XTIGGAHUZJWQMD-UHFFFAOYSA-N 0.000 description 5
- XLDLRRGZWIEEHT-UHFFFAOYSA-N 3-hydroxy-4-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C(O)=C1 XLDLRRGZWIEEHT-UHFFFAOYSA-N 0.000 description 5
- 240000006995 Abutilon theophrasti Species 0.000 description 5
- 244000277285 Cassia obtusifolia Species 0.000 description 5
- 235000006719 Cassia obtusifolia Nutrition 0.000 description 5
- 244000100545 Lolium multiflorum Species 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 240000006394 Sorghum bicolor Species 0.000 description 5
- 241001141210 Urochloa platyphylla Species 0.000 description 5
- 125000005907 alkyl ester group Chemical group 0.000 description 5
- 229940050390 benzoate Drugs 0.000 description 5
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 5
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 5
- 239000000428 dust Substances 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 231100000208 phytotoxic Toxicity 0.000 description 5
- 230000000885 phytotoxic effect Effects 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
- 241000209764 Avena fatua Species 0.000 description 4
- 235000007320 Avena fatua Nutrition 0.000 description 4
- 235000014552 Cassia tora Nutrition 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
- 235000003403 Limnocharis flava Nutrition 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 235000006923 Sorghum x drummondii Nutrition 0.000 description 4
- 208000027418 Wounds and injury Diseases 0.000 description 4
- 241001506766 Xanthium Species 0.000 description 4
- 150000001559 benzoic acids Chemical class 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 150000001805 chlorine compounds Chemical class 0.000 description 4
- 230000006378 damage Effects 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 4
- 238000007429 general method Methods 0.000 description 4
- 208000014674 injury Diseases 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 231100000167 toxic agent Toxicity 0.000 description 4
- 239000003440 toxic substance Substances 0.000 description 4
- 238000009736 wetting Methods 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- 238000010626 work up procedure Methods 0.000 description 4
- MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 240000001592 Amaranthus caudatus Species 0.000 description 3
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 3
- 235000004535 Avena sterilis Nutrition 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 235000005853 Cyperus esculentus Nutrition 0.000 description 3
- 241000103725 Cyperus esculentus var. esculentus Species 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 244000275012 Sesbania cannabina Species 0.000 description 3
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000003973 alkyl amines Chemical class 0.000 description 3
- 239000002168 alkylating agent Substances 0.000 description 3
- 229940100198 alkylating agent Drugs 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical class O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- NXYCTVGRJYPWOF-UHFFFAOYSA-N ethyl 2-bromo-3-hydroxy-4-nitrobenzoate Chemical compound CCOC(=O)C1=CC=C([N+]([O-])=O)C(O)=C1Br NXYCTVGRJYPWOF-UHFFFAOYSA-N 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 3
- 230000008707 rearrangement Effects 0.000 description 3
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 3
- GBNVXYXIRHSYEG-UHFFFAOYSA-N 1-chloro-2-ethylsulfanylethane Chemical compound CCSCCCl GBNVXYXIRHSYEG-UHFFFAOYSA-N 0.000 description 2
- MYFKLQFBFSHBPA-UHFFFAOYSA-N 1-chloro-2-methylsulfanylethane Chemical compound CSCCCl MYFKLQFBFSHBPA-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 244000058871 Echinochloa crus-galli Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- 241000533293 Sesbania emerus Species 0.000 description 2
- 240000003461 Setaria viridis Species 0.000 description 2
- 235000002248 Setaria viridis Nutrition 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- DOZWCONHUMHEPS-UHFFFAOYSA-N Tetramethylphloroglucin Natural products CC1(C)C(=O)CC(=O)C(C)(C)C1=O DOZWCONHUMHEPS-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 229910000318 alkali metal phosphate Inorganic materials 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000001351 alkyl iodides Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- GJQBHOAJJGIPRH-UHFFFAOYSA-N benzoyl cyanide Chemical compound N#CC(=O)C1=CC=CC=C1 GJQBHOAJJGIPRH-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 2
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 229940043279 diisopropylamine Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- MDSSLDOBFUPLGM-UHFFFAOYSA-N ethyl 2,4-dibromo-3-(2-methoxyethoxy)benzoate Chemical compound CCOC(=O)C1=CC=C(Br)C(OCCOC)=C1Br MDSSLDOBFUPLGM-UHFFFAOYSA-N 0.000 description 2
- WDRYGTBLAOZBAF-UHFFFAOYSA-N ethyl 2,4-dichloro-3-hydroxybenzoate Chemical compound CCOC(=O)C1=CC=C(Cl)C(O)=C1Cl WDRYGTBLAOZBAF-UHFFFAOYSA-N 0.000 description 2
- NOPMWCKLGHBWTM-UHFFFAOYSA-N ethyl 2-bromo-3-(2-methoxyethoxy)-4-nitrobenzoate Chemical compound CCOC(=O)C1=CC=C([N+]([O-])=O)C(OCCOC)=C1Br NOPMWCKLGHBWTM-UHFFFAOYSA-N 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- 150000004965 peroxy acids Chemical class 0.000 description 2
- 239000003444 phase transfer catalyst Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 229920000056 polyoxyethylene ether Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
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- NVGOPFQZYCNLDU-UHFFFAOYSA-N norflurazon Chemical compound O=C1C(Cl)=C(NC)C=NN1C1=CC=CC(C(F)(F)F)=C1 NVGOPFQZYCNLDU-UHFFFAOYSA-N 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- LCHWKMAWSZDQRD-UHFFFAOYSA-N silylformonitrile Chemical class [SiH3]C#N LCHWKMAWSZDQRD-UHFFFAOYSA-N 0.000 description 1
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- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
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- 235000012976 tarts Nutrition 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 125000005270 trialkylamine group Chemical group 0.000 description 1
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- 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
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
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Classifications
-
- 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
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
-
- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/10—Sulfones; Sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/59—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/24—Sulfones; Sulfoxides having sulfone or sulfoxide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/24—Halogenated derivatives
- C07C39/26—Halogenated derivatives monocyclic monohydroxylic containing halogen bound to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
- C07C65/03—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Pest Control & Pesticides (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Led Device Packages (AREA)
- Lubricants (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Liquid Crystal Substances (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/273,371 US4957538A (en) | 1988-11-18 | 1988-11-18 | Certain 2-(2',3',4'-trisubstituted benzoyl)-1,3-cyclohexanediones |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL92341A0 IL92341A0 (en) | 1990-07-26 |
| IL92341A true IL92341A (en) | 1994-10-21 |
Family
ID=23043626
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9234189A IL92341A (en) | 1988-11-18 | 1989-11-17 | 2-) Benzoyl- (2, (3,) (4-trimethyl) (1,3-cyclohexanediones and their use as herbicides |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4957538A (cs) |
| EP (1) | EP0444152B1 (cs) |
| JP (1) | JP2714479B2 (cs) |
| KR (1) | KR0143406B1 (cs) |
| CN (1) | CN1024187C (cs) |
| AT (1) | ATE123752T1 (cs) |
| AU (1) | AU635725B2 (cs) |
| BR (1) | BR8907772A (cs) |
| CA (1) | CA2003172C (cs) |
| CZ (1) | CZ283556B6 (cs) |
| DE (1) | DE68923088T2 (cs) |
| ES (1) | ES2073561T3 (cs) |
| HU (1) | HU206663B (cs) |
| IL (1) | IL92341A (cs) |
| MY (1) | MY104271A (cs) |
| PH (1) | PH26116A (cs) |
| PL (1) | PL159535B1 (cs) |
| RO (1) | RO110333B1 (cs) |
| RU (1) | RU2045512C1 (cs) |
| SK (1) | SK649089A3 (cs) |
| TR (1) | TR24909A (cs) |
| WO (1) | WO1990005712A1 (cs) |
| YU (1) | YU48303B (cs) |
| ZA (1) | ZA898781B (cs) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2739738B2 (ja) * | 1987-10-19 | 1998-04-15 | 日産化学工業株式会社 | 置換ベンゾイル誘導体および選択性除草剤 |
| US5041613A (en) * | 1989-08-28 | 1991-08-20 | Eastman Kodak Company | Organic compositions and their manufacture |
| US5092919A (en) * | 1991-01-15 | 1992-03-03 | Imperial Chemical Industries Plc | Certain 2-(2'-methyl-3',4'-trisubstituted benzoyl)-1,3-cyclohexanediones |
| ZM5092A1 (en) * | 1991-08-01 | 1994-04-25 | Ici America Inc | 2-(2-chloro-3ethoxy-4-ethylsulfonyl)-5-methyl-1,3-cyclohexanedione |
| US5152826A (en) * | 1991-10-16 | 1992-10-06 | Imperial Chemical Industries Plc | Certain substituted bis(2-benzoyl-3-oxo-cyclohexenyl) thioglycols |
| US6004903A (en) * | 1995-02-24 | 1999-12-21 | Basf Aktiengesellschaft | 2-Anylocyclohexanediones having improved herbicidal properties |
| DE19532311A1 (de) * | 1995-09-01 | 1997-03-06 | Basf Ag | Benzoylderivate |
| DE19700019A1 (de) | 1997-01-03 | 1998-07-09 | Basf Ag | Substituierte 2-Benzoyl-cyclohexan-1,3-dione |
| AU7427298A (en) * | 1997-03-14 | 1998-10-12 | Novartis Ag | Novel herbicides |
| WO1998042648A1 (en) * | 1997-03-24 | 1998-10-01 | Dow Agrosciences Llc | 2-benzoylcyclohexane-1,3-dione compounds and their use as herbicides |
| DE19846792A1 (de) * | 1998-10-10 | 2000-04-13 | Hoechst Schering Agrevo Gmbh | Benzoylcyclohexandione, Verfahren zur ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
| PL363949A1 (en) * | 2001-05-16 | 2004-11-29 | Bayer Cropscience Ag | Substituted benzoylcyclohexenones and their use as herbicidal agents |
| DE10144529A1 (de) | 2001-09-11 | 2003-03-27 | Bayer Cropscience Gmbh | 3-Aminocarbonyl substituierte Benzoylcyclohexandione |
| DE10209645A1 (de) * | 2002-03-05 | 2003-09-18 | Bayer Cropscience Ag | Substituierte Arylketone |
| CN1960967B (zh) * | 2004-06-03 | 2010-12-29 | 石原产业株式会社 | 三酮类化合物、其制造方法及含有该类化合物的除草剂 |
| US9169219B2 (en) | 2012-02-21 | 2015-10-27 | Bayer Intellectual Property Gmbh | Herbicidally active 4-nitro-substituted N-(tetrazol-5-yl)-, N-(triazol-5-yl)-, and N-(1,3,4-0XADIAZOL-2-yl)aryl carboxylic acid amides |
| CN110776410B (zh) * | 2019-11-28 | 2020-08-21 | 东北农业大学 | 一种含肉桂酰基的三酮类化合物、制备方法及其应用 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0005709B1 (de) * | 1978-03-15 | 1981-12-09 | Ciba-Geigy Ag | Herbizid wirksame substituierte Diphenylätherderivate, diese als Wirkstoffe enthaltende herbizide Mittel und deren Verwendung |
| EP0090262B1 (en) * | 1982-03-25 | 1992-08-05 | Stauffer Chemical Company | Certain 2-(2-substituted benzoyl)-1,3-cyclohexanediones |
| US4780127A (en) * | 1982-03-25 | 1988-10-25 | Stauffer Chemical Company | Certain 2-(substituted benzoyl)-1,3-cyclohexanediones and their use as herbicides |
| US4797150A (en) * | 1986-06-09 | 1989-01-10 | Stauffer Chemical Company | Certain 2-(2-substituted benzoyl)-1,3,5-cyclohexanetriones |
| PH21446A (en) * | 1983-09-16 | 1987-10-20 | Stauffer Chemical Co | Certain 2-(2-substituted benzoyl)-1,3-cyclohexanediones |
| EP0137963B1 (en) * | 1983-09-16 | 1988-09-28 | Stauffer Chemical Company | Certain 2-(2-substituted benzoyl)-1,3-cyclohexanediones |
| US4918236A (en) * | 1986-06-09 | 1990-04-17 | Ici Americas Inc. | Certain substituted 3-(substituted oxy)-2-benzoyl-cyclohex-2-enones |
| NZ220338A (en) * | 1986-06-09 | 1989-09-27 | Stauffer Chemical Co | 2-benzoyl-1,3,5-cyclohexanetrione derivatives and herbicidal compositions |
| KR890003680A (ko) * | 1986-10-16 | 1989-04-17 | 죤 알.페넬 | 2-(2-치환 벤조일)-4-(치환)-1,3-시클로헥산디온 및 그 제조방법과 이를 이용한 조성물 및 식물체의 억제방법 |
| US4783213A (en) * | 1986-10-16 | 1988-11-08 | Stauffer Chemical Company | Certain 2-(2-substituted benzoyl)-4-(substituted oxy or substituted thio)-1,3-cyclohexanediones |
| US4925965A (en) * | 1987-11-19 | 1990-05-15 | Ici Americas Inc. | Certain 2-benzoyl-5-hydroxy-4,4,6,6-tetra-substituted-1,3-cyclohexanediones |
-
1988
- 1988-11-18 US US07/273,371 patent/US4957538A/en not_active Expired - Lifetime
-
1989
- 1989-11-10 TR TR89/0955A patent/TR24909A/xx unknown
- 1989-11-15 YU YU217589A patent/YU48303B/sh unknown
- 1989-11-15 MY MYPI89001590A patent/MY104271A/en unknown
- 1989-11-16 CZ CS896490A patent/CZ283556B6/cs not_active IP Right Cessation
- 1989-11-16 CA CA002003172A patent/CA2003172C/en not_active Expired - Fee Related
- 1989-11-16 SK SK6490-89A patent/SK649089A3/sk unknown
- 1989-11-17 DE DE68923088T patent/DE68923088T2/de not_active Expired - Fee Related
- 1989-11-17 RO RO147547A patent/RO110333B1/ro unknown
- 1989-11-17 RU SU894895472A patent/RU2045512C1/ru active
- 1989-11-17 PL PL1989282350A patent/PL159535B1/pl unknown
- 1989-11-17 PH PH39551A patent/PH26116A/en unknown
- 1989-11-17 KR KR1019900701550A patent/KR0143406B1/ko not_active Expired - Fee Related
- 1989-11-17 JP JP2501218A patent/JP2714479B2/ja not_active Expired - Lifetime
- 1989-11-17 ES ES90901166T patent/ES2073561T3/es not_active Expired - Lifetime
- 1989-11-17 IL IL9234189A patent/IL92341A/en not_active IP Right Cessation
- 1989-11-17 ZA ZA898781A patent/ZA898781B/xx unknown
- 1989-11-17 CN CN89108603A patent/CN1024187C/zh not_active Expired - Fee Related
- 1989-11-17 AU AU47433/90A patent/AU635725B2/en not_active Ceased
- 1989-11-17 BR BR898907772A patent/BR8907772A/pt not_active IP Right Cessation
- 1989-11-17 AT AT90901166T patent/ATE123752T1/de not_active IP Right Cessation
- 1989-11-17 HU HU90499A patent/HU206663B/hu not_active IP Right Cessation
- 1989-11-17 WO PCT/US1989/005056 patent/WO1990005712A1/en not_active Ceased
- 1989-11-17 EP EP90901166A patent/EP0444152B1/en not_active Expired - Lifetime
Also Published As
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Legal Events
| Date | Code | Title | Description |
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| KB | Patent renewed | ||
| KB | Patent renewed | ||
| HP | Change in proprietorship | ||
| RH1 | Patent not in force | ||
| HC | Change of name of proprietor(s) |