IL104752A - Imidazopyrrolo-pyridinediones useful as intermediates for the preparation of herbicidal nicotinic acids, esters and salts - Google Patents
Imidazopyrrolo-pyridinediones useful as intermediates for the preparation of herbicidal nicotinic acids, esters and saltsInfo
- Publication number
- IL104752A IL104752A IL10475288A IL10475288A IL104752A IL 104752 A IL104752 A IL 104752A IL 10475288 A IL10475288 A IL 10475288A IL 10475288 A IL10475288 A IL 10475288A IL 104752 A IL104752 A IL 104752A
- Authority
- IL
- Israel
- Prior art keywords
- optionally substituted
- halogens
- methyl
- phenyl
- alkyl
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 5
- 238000002360 preparation method Methods 0.000 title abstract description 49
- 150000002148 esters Chemical class 0.000 title abstract description 10
- 239000000543 intermediate Substances 0.000 title abstract description 4
- 235000001968 nicotinic acid Nutrition 0.000 title description 25
- 230000002363 herbicidal effect Effects 0.000 title description 12
- 150000002814 niacins Chemical class 0.000 title description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 38
- 150000002367 halogens Chemical class 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- 125000003282 alkyl amino group Chemical group 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 7
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000005208 trialkylammonium group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 4
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000000466 oxiranyl group Chemical group 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 239000004009 herbicide Substances 0.000 abstract description 8
- DIABIDLZBNRSPR-UHFFFAOYSA-N 2-carbamoylpyridine-3-carboxylic acid Chemical class NC(=O)C1=NC=CC=C1C(O)=O DIABIDLZBNRSPR-UHFFFAOYSA-N 0.000 abstract 1
- CHIPPOYVYLAENM-UHFFFAOYSA-N 2-imidazolidin-2-ylpyridine-3-carboxylic acid Chemical class OC(=O)C1=CC=CN=C1C1NCCN1 CHIPPOYVYLAENM-UHFFFAOYSA-N 0.000 abstract 1
- TXTSUZLKJKLIQY-UHFFFAOYSA-N acetamide;1h-pyrrolo[3,2-b]pyridine Chemical class CC(N)=O.C1=CC=C2NC=CC2=N1 TXTSUZLKJKLIQY-UHFFFAOYSA-N 0.000 abstract 1
- 150000005255 pyrrolopyridines Chemical class 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 74
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 72
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 239000000203 mixture Substances 0.000 description 45
- 238000006243 chemical reaction Methods 0.000 description 38
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
- 239000000047 product Substances 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 28
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 27
- 229940073584 methylene chloride Drugs 0.000 description 24
- 239000011664 nicotinic acid Substances 0.000 description 23
- -1 benzyloxy, furyl Chemical group 0.000 description 21
- 239000007787 solid Substances 0.000 description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000003921 oil Substances 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 238000000034 method Methods 0.000 description 15
- 241000196324 Embryophyta Species 0.000 description 14
- 238000010992 reflux Methods 0.000 description 14
- 239000000741 silica gel Substances 0.000 description 14
- 229910002027 silica gel Inorganic materials 0.000 description 14
- YNBADRVTZLEFNH-UHFFFAOYSA-N methyl nicotinate Chemical compound COC(=O)C1=CC=CN=C1 YNBADRVTZLEFNH-UHFFFAOYSA-N 0.000 description 13
- 239000012074 organic phase Substances 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 244000075850 Avena orientalis Species 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 229960003512 nicotinic acid Drugs 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- 235000007319 Avena orientalis Nutrition 0.000 description 8
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 8
- 150000004702 methyl esters Chemical class 0.000 description 8
- 241001049165 Caria Species 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 241001290610 Abildgaardia Species 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 101000978836 Rattus norvegicus Glycoprotein endo-alpha-1,2-mannosidase Proteins 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 239000002243 precursor Substances 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- 238000007792 addition Methods 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 229940093499 ethyl acetate Drugs 0.000 description 5
- 235000019439 ethyl acetate Nutrition 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000012038 nucleophile Substances 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000012258 stirred mixture Substances 0.000 description 4
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 description 3
- NUPJIGQFXCQJBK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)-5-(methoxymethyl)nicotinic acid Chemical compound OC(=O)C1=CC(COC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 NUPJIGQFXCQJBK-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 229940086542 triethylamine Drugs 0.000 description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 2
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
- VZAWCLCJGSBATP-UHFFFAOYSA-N 1-cycloundecyl-1,2-diazacycloundecane Chemical compound C1CCCCCCCCCC1N1NCCCCCCCCC1 VZAWCLCJGSBATP-UHFFFAOYSA-N 0.000 description 2
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- CGMJIXLCLAOYLR-UHFFFAOYSA-N 2-(4,5-dihydro-1h-imidazol-2-yl)pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1C1=NCCN1 CGMJIXLCLAOYLR-UHFFFAOYSA-N 0.000 description 2
- PPHNKKGTJWJULK-UHFFFAOYSA-N 2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)-5-thiophen-2-ylpyridine-3-carboxylic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC=C(C=2SC=CC=2)C=C1C(O)=O PPHNKKGTJWJULK-UHFFFAOYSA-N 0.000 description 2
- JJMDTERTPNYIGZ-UHFFFAOYSA-N 2-cyclohexylacetaldehyde Chemical compound O=CCC1CCCCC1 JJMDTERTPNYIGZ-UHFFFAOYSA-N 0.000 description 2
- JLJSCLYUDCQETH-UHFFFAOYSA-N 3-(chloromethyl)furo[3,4-b]pyridine-5,7-dione Chemical compound ClCC1=CN=C2C(=O)OC(=O)C2=C1 JLJSCLYUDCQETH-UHFFFAOYSA-N 0.000 description 2
- JFAMDMZZOQJYDN-UHFFFAOYSA-N 5-(hydroxymethyl)-6-methylpyridine-2,3-dicarboxylic acid Chemical compound CC1=NC(C(O)=O)=C(C(O)=O)C=C1CO JFAMDMZZOQJYDN-UHFFFAOYSA-N 0.000 description 2
- TZBODSUSRFGUPV-UHFFFAOYSA-N 5-acetylpyridine-2,3-dicarboxylic acid Chemical compound CC(=O)C1=CN=C(C(O)=O)C(C(O)=O)=C1 TZBODSUSRFGUPV-UHFFFAOYSA-N 0.000 description 2
- HQDBPGQEZCFJTL-UHFFFAOYSA-N 5-cyclohexyl-2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)pyridine-3-carboxylic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC=C(C2CCCCC2)C=C1C(O)=O HQDBPGQEZCFJTL-UHFFFAOYSA-N 0.000 description 2
- KTMPCKPDVKBKBU-UHFFFAOYSA-N 5-cyclohexylpyridine-2,3-dicarboxylic acid Chemical compound N1=C(C(O)=O)C(C(=O)O)=CC(C2CCCCC2)=C1 KTMPCKPDVKBKBU-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 240000001592 Amaranthus caudatus Species 0.000 description 2
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 2
- 244000036975 Ambrosia artemisiifolia Species 0.000 description 2
- 235000007320 Avena fatua Nutrition 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- 241000335053 Beta vulgaris Species 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 2
- 244000075634 Cyperus rotundus Species 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 101100295741 Gallus gallus COR4 gene Proteins 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- 244000098338 Triticum aestivum Species 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 2
- 150000008046 alkali metal hydrides Chemical class 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 2
- HUMHYXGDUOGHTG-HEZXSMHISA-N alpha-D-GalpNAc-(1->3)-[alpha-L-Fucp-(1->2)]-D-Galp Chemical compound O[C@H]1[C@H](O)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](O[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](O)[C@@H](CO)OC1O HUMHYXGDUOGHTG-HEZXSMHISA-N 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 229960000892 attapulgite Drugs 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- PSTYFNYTPMECBG-UHFFFAOYSA-N dimethyl 6-chloro-5-(2-chloroethyl)pyridine-2,3-dicarboxylate Chemical compound COC(=O)C1=CC(CCCl)=C(Cl)N=C1C(=O)OC PSTYFNYTPMECBG-UHFFFAOYSA-N 0.000 description 2
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 2
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- 239000004094 surface-active agent Substances 0.000 description 1
- FBWNMEQMRUMQSO-UHFFFAOYSA-N tergitol NP-9 Chemical compound CCCCCCCCCC1=CC=C(OCCOCCOCCOCCOCCOCCOCCOCCOCCO)C=C1 FBWNMEQMRUMQSO-UHFFFAOYSA-N 0.000 description 1
- 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
- 230000000007 visual effect Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed systems contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- 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
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13999687A | 1987-12-31 | 1987-12-31 | |
| IL88663A IL88663A0 (en) | 1987-12-31 | 1988-12-12 | Novel 5(and/or 6)substituted 2-(2-(imidazolin-2-yl)nicotinic acids,esters and salts,useful as herbicidal agents and novel intermediates for the preparation of said nicotinic acids,esters and salts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL104752A true IL104752A (en) | 1994-05-30 |
Family
ID=22489255
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL10475288A IL104752A (en) | 1987-12-31 | 1988-12-12 | Imidazopyrrolo-pyridinediones useful as intermediates for the preparation of herbicidal nicotinic acids, esters and salts |
| IL10475188A IL104751A (en) | 1987-12-31 | 1988-12-12 | Substituted pyrrolopyridine acetonitriles and acetamides and carbamoyl nicotinic acids, esters and salts useful as intermediates for the preparation of herbicidal nicotinic acids, esters and salts |
| IL88663A IL88663A0 (en) | 1987-12-31 | 1988-12-12 | Novel 5(and/or 6)substituted 2-(2-(imidazolin-2-yl)nicotinic acids,esters and salts,useful as herbicidal agents and novel intermediates for the preparation of said nicotinic acids,esters and salts |
| IL104751A IL104751A0 (en) | 1987-12-31 | 1993-02-16 | Novel 5(and/or 6)substituted 2-(2-imidazolin-2-yl)nicotinic acids,esters and salts,useful as herbicidal agents and novel intermediates for the preparation of said nicotinic acis,esters and salts |
| IL104752A IL104752A0 (en) | 1987-12-31 | 1993-02-16 | Novel 5(and/or 6)substituted 2-(2-imidazolin-2-yl)nicotinic acids,esters and salts,useful as herbicidal agents and novel intermediates for the preparation of said nicotinic acids,esters and salts |
Family Applications After (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL10475188A IL104751A (en) | 1987-12-31 | 1988-12-12 | Substituted pyrrolopyridine acetonitriles and acetamides and carbamoyl nicotinic acids, esters and salts useful as intermediates for the preparation of herbicidal nicotinic acids, esters and salts |
| IL88663A IL88663A0 (en) | 1987-12-31 | 1988-12-12 | Novel 5(and/or 6)substituted 2-(2-(imidazolin-2-yl)nicotinic acids,esters and salts,useful as herbicidal agents and novel intermediates for the preparation of said nicotinic acids,esters and salts |
| IL104751A IL104751A0 (en) | 1987-12-31 | 1993-02-16 | Novel 5(and/or 6)substituted 2-(2-imidazolin-2-yl)nicotinic acids,esters and salts,useful as herbicidal agents and novel intermediates for the preparation of said nicotinic acis,esters and salts |
| IL104752A IL104752A0 (en) | 1987-12-31 | 1993-02-16 | Novel 5(and/or 6)substituted 2-(2-imidazolin-2-yl)nicotinic acids,esters and salts,useful as herbicidal agents and novel intermediates for the preparation of said nicotinic acids,esters and salts |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP0322616A3 (da) |
| JP (1) | JPH02779A (da) |
| KR (1) | KR970005304B1 (da) |
| AU (2) | AU612750B2 (da) |
| BR (1) | BR8806959A (da) |
| CA (1) | CA1337423C (da) |
| DK (3) | DK733188A (da) |
| HU (1) | HU205832B (da) |
| IE (1) | IE81168B1 (da) |
| IL (5) | IL104752A (da) |
| ZA (1) | ZA889728B (da) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5062881A (en) * | 1989-12-20 | 1991-11-05 | American Cyanamid Company | 2-(1-substituted-2-imidazolin-2-yl)benzoic and nicotinic acids and a method for their preparation |
| ATE166350T1 (de) * | 1989-12-27 | 1998-06-15 | American Cyanamid Co | Alkylester von 5-heterocyclische-pyridin-2,3- dicarbonsäuren und 5-heterocyclische-2-(2- imidazolin-2-yl)pyridinen und verfahren zu ihrer herstellung |
| KR920003063B1 (ko) * | 1990-02-28 | 1992-04-13 | 재단법인 한국화학연구소 | 신규한2-(2-이미다졸린-2-일)-3-(아미노옥소아세틸)-피리딘유도체와그염 |
| WO1992009577A1 (en) * | 1990-11-22 | 1992-06-11 | Janssen Pharmaceutica N.V. | Isonicotinic acid derivatives and related spiro compounds with herbicidal action |
| US5215568A (en) * | 1991-10-31 | 1993-06-01 | American Cyanamid Company | Oxime derivatives of formylpyridyl imidazolinones, the herbicidal use and methods for the preparation thereof |
| EP0623281A1 (en) * | 1993-04-28 | 1994-11-09 | American Cyanamid Company | Herbicidal extruded granular compositions |
| DE4343922A1 (de) * | 1993-12-22 | 1995-06-29 | Basf Ag | Pyridin-2,3-dicarbonsäureimide, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwuchses |
| KR100246964B1 (ko) * | 1996-11-28 | 2000-03-15 | 윤종용 | 반도체 스피너장비 |
| CN102245578B (zh) * | 2008-11-13 | 2015-01-07 | 巴斯夫欧洲公司 | 制备5-氯甲基-2,3-吡啶二甲酸酐的方法 |
| CN102245577B (zh) * | 2008-11-13 | 2014-03-26 | 巴斯夫欧洲公司 | 2-[(1-氰基丙基)氨基甲酰基]-5-氯甲基烟酸及其在制备除草咪唑啉酮中的用途 |
| WO2010055042A1 (en) * | 2008-11-13 | 2010-05-20 | Basf Se | 2-[(1-cyanopropyl)carbamoyl]-5-methoxymethyl nicotinic acids and the use thereof in manufacturing herbicidal imidazolinones |
| EP2365965B1 (en) | 2008-11-13 | 2019-01-09 | Basf Se | Process for manufacturing substituted 3-pyridylmethyl ammonium bromides |
| TWI506019B (zh) | 2008-12-08 | 2015-11-01 | Basf Se | 製造經取代５－甲氧基甲基吡啶－２，３－二羧酸衍生物之方法 |
| ES2670677T3 (es) | 2008-12-09 | 2018-05-31 | Basf Se | Procedimiento de fabricación de anhídrido 5-clorometil-2,3-dicarboxílico |
| EP3782985A1 (en) | 2019-08-19 | 2021-02-24 | BASF Agrochemical Products B.V. | Process for manufacturing 5-methoxymethylpyridine-2,3-dicarboxylic acid derivatives |
| CN118291167B (zh) * | 2023-01-03 | 2025-11-04 | 中国石油化工股份有限公司 | 一种溶剂脱沥青生产脱沥青油的方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR241812A1 (es) * | 1983-08-02 | 1992-12-30 | American Cyanamit Company | Nuevas hidroimidazo pirrolopirinas, o vinolinas, tieno-y furo¡2,3b¿ piridinas dihidrotieno-y furo ¡2,3b¿ piridinas, tieno-y furo ¡3,2b¿ piridinas tautomeros de las mismas. |
| EP0166907A3 (en) * | 1984-06-04 | 1988-09-14 | American Cyanamid Company | Herbicidal 2-(2-imidazolin-2-yl)-fluoroalkoxy-, alkenyloxy- and alkynyloxypyridines and quinolines |
| US4709036A (en) * | 1985-06-13 | 1987-11-24 | American Cyanamid Company | Process for the preparation of herbicidal 2-(4,4-disubstituted-5-oxo-2-imidazolin-2-yl)benzoic, nicotinic and quinoline-3-carboxylic acids, esters and salts |
| SU1560052A3 (ru) * | 1985-09-24 | 1990-04-23 | Шеринг Аг (Фирма) | Гербицидное средство |
| GB2192877A (en) * | 1986-07-22 | 1988-01-27 | Shell Int Research | Herbicidal imidazolinyl compounds |
| ES2076927T3 (es) * | 1986-07-28 | 1995-11-16 | American Cyanamid Co | Nuevos acidos 2-(2-imidazolin-2-il)nicotinicos 5(y/o 6) sustituidos, sus esteres y sus sales, utiles como agentes herbicidas y nuevos compuestos intermedios para la preparacion de dichos acidos nicotinicos, esteres y sales. |
| EP0296109A3 (de) * | 1987-06-18 | 1989-12-20 | Ciba-Geigy Ag | 2-(Imidazolin-2-yl)nicotinsäurederivate |
-
1988
- 1988-12-09 EP EP88120594A patent/EP0322616A3/en not_active Withdrawn
- 1988-12-12 IL IL10475288A patent/IL104752A/en not_active IP Right Cessation
- 1988-12-12 IL IL10475188A patent/IL104751A/en not_active IP Right Cessation
- 1988-12-12 IL IL88663A patent/IL88663A0/xx not_active IP Right Cessation
- 1988-12-28 JP JP63329496A patent/JPH02779A/ja active Pending
- 1988-12-29 CA CA000587213A patent/CA1337423C/en not_active Expired - Lifetime
- 1988-12-29 ZA ZA889728A patent/ZA889728B/xx unknown
- 1988-12-29 BR BR888806959A patent/BR8806959A/pt not_active Application Discontinuation
- 1988-12-30 AU AU27583/88A patent/AU612750B2/en not_active Expired
- 1988-12-30 HU HU886681A patent/HU205832B/hu not_active IP Right Cessation
- 1988-12-30 DK DK733188A patent/DK733188A/da not_active Application Discontinuation
- 1988-12-30 KR KR1019880018228A patent/KR970005304B1/ko not_active Expired - Fee Related
- 1988-12-30 IE IE389088A patent/IE81168B1/en not_active IP Right Cessation
-
1991
- 1991-05-21 AU AU77208/91A patent/AU7720891A/en not_active Abandoned
-
1993
- 1993-02-16 IL IL104751A patent/IL104751A0/xx unknown
- 1993-02-16 IL IL104752A patent/IL104752A0/xx unknown
- 1993-09-17 DK DK931041A patent/DK104193D0/da not_active Application Discontinuation
- 1993-09-17 DK DK931042A patent/DK104293D0/da not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0322616A2 (en) | 1989-07-05 |
| IE81168B1 (en) | 2000-05-31 |
| DK104193A (da) | 1993-09-17 |
| JPH02779A (ja) | 1990-01-05 |
| IL104751A (en) | 1994-05-30 |
| IL104751A0 (en) | 1993-06-10 |
| IL104752A0 (en) | 1993-06-10 |
| HUT49457A (en) | 1989-10-30 |
| DK733188A (da) | 1989-07-01 |
| DK104193D0 (da) | 1993-09-17 |
| AU612750B2 (en) | 1991-07-18 |
| IE883890L (en) | 1989-06-30 |
| IL88663A0 (en) | 1989-07-31 |
| EP0322616A3 (en) | 1989-10-18 |
| ZA889728B (en) | 1989-10-25 |
| KR890009928A (ko) | 1989-08-04 |
| HU205832B (en) | 1992-07-28 |
| KR970005304B1 (ko) | 1997-04-15 |
| DK104293A (da) | 1993-09-17 |
| DK733188D0 (da) | 1988-12-30 |
| CA1337423C (en) | 1995-10-24 |
| AU7720891A (en) | 1991-08-08 |
| AU2758388A (en) | 1989-07-06 |
| BR8806959A (pt) | 1989-08-29 |
| DK104293D0 (da) | 1993-09-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| KB | Patent renewed | ||
| RH1 | Patent not in force |