CA1109878A - Imidazolinyl benzoic acids esters and salts - Google Patents
Imidazolinyl benzoic acids esters and saltsInfo
- Publication number
- CA1109878A CA1109878A CA307,740A CA307740A CA1109878A CA 1109878 A CA1109878 A CA 1109878A CA 307740 A CA307740 A CA 307740A CA 1109878 A CA1109878 A CA 1109878A
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- alkyl
- oxo
- imidazolin
- isopropyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 18
- VSGNJFMJPJJRTQ-UHFFFAOYSA-N 2-(4,5-dihydroimidazol-1-yl)benzoic acid Chemical class OC(=O)C1=CC=CC=C1N1C=NCC1 VSGNJFMJPJJRTQ-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 68
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 47
- -1 cyclohexenylmethyl Chemical group 0.000 claims abstract description 38
- 241000196324 Embryophyta Species 0.000 claims abstract description 37
- 239000000203 mixture Substances 0.000 claims abstract description 36
- 239000001257 hydrogen Substances 0.000 claims abstract description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 29
- 238000000034 method Methods 0.000 claims abstract description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 24
- 239000002253 acid Substances 0.000 claims abstract description 22
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 20
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 18
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 17
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 17
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 16
- 230000003287 optical effect Effects 0.000 claims abstract description 15
- 238000002360 preparation method Methods 0.000 claims abstract description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 12
- 150000001768 cations Chemical class 0.000 claims abstract description 12
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 11
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 10
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 9
- 150000002367 halogens Chemical class 0.000 claims abstract description 9
- 239000002689 soil Substances 0.000 claims abstract description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 8
- 210000000056 organ Anatomy 0.000 claims abstract description 8
- 230000001902 propagating effect Effects 0.000 claims abstract description 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 7
- 125000002541 furyl group Chemical group 0.000 claims abstract description 7
- 125000005059 halophenyl group Chemical group 0.000 claims abstract description 7
- 150000002431 hydrogen Chemical group 0.000 claims abstract 14
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract 12
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims abstract 4
- 239000000460 chlorine Chemical group 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 13
- GCFBDIVEVTXDJZ-UHFFFAOYSA-N pyrrolo[3,4-e]benzimidazole-2,4-dione Chemical compound O=C1C2=NC(=O)N=C2C2=CN=CC2=C1 GCFBDIVEVTXDJZ-UHFFFAOYSA-N 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 125000002636 imidazolinyl group Chemical group 0.000 claims description 6
- 239000011734 sodium Chemical class 0.000 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- 239000003586 protic polar solvent Substances 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims description 4
- 239000011261 inert gas Substances 0.000 claims description 4
- 150000008046 alkali metal hydrides Chemical class 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 2
- RCVABMZVLZNJAG-UHFFFAOYSA-N 2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)benzoic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=CC=CC=C1C(O)=O RCVABMZVLZNJAG-UHFFFAOYSA-N 0.000 claims 14
- DYUWOEUKAVJUDA-UHFFFAOYSA-N 3-methyl-4-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)benzoic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=CC=C(C(O)=O)C=C1C DYUWOEUKAVJUDA-UHFFFAOYSA-N 0.000 claims 3
- DICZSROBUFDHMN-UHFFFAOYSA-N 4-methyl-3-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)benzoic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=CC(C(O)=O)=CC=C1C DICZSROBUFDHMN-UHFFFAOYSA-N 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- GGCPXJNERJTHHL-UHFFFAOYSA-N 2-(4-ethyl-4-methyl-5-oxo-1h-imidazol-2-yl)benzoic acid Chemical compound O=C1C(CC)(C)NC(C=2C(=CC=CC=2)C(O)=O)=N1 GGCPXJNERJTHHL-UHFFFAOYSA-N 0.000 claims 1
- VRCWMVAZCHCQOK-UHFFFAOYSA-N 2-chloro-6-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)benzoic acid Chemical compound O=C1C(C(C)C)(C)NC(C=2C(=C(Cl)C=CC=2)C(O)=O)=N1 VRCWMVAZCHCQOK-UHFFFAOYSA-N 0.000 claims 1
- YHSJKUNHKAONQP-UHFFFAOYSA-N 3-chloro-2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)benzoic acid Chemical compound O=C1C(C(C)C)(C)NC(C=2C(=CC=CC=2Cl)C(O)=O)=N1 YHSJKUNHKAONQP-UHFFFAOYSA-N 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 229940083542 sodium Drugs 0.000 claims 1
- 235000015424 sodium Nutrition 0.000 claims 1
- JOTLWQUUMCNABN-UHFFFAOYSA-N n-(4,5-dihydroimidazol-1-yl)benzamide Chemical class C=1C=CC=CC=1C(=O)NN1CCN=C1 JOTLWQUUMCNABN-UHFFFAOYSA-N 0.000 abstract description 4
- 235000013350 formula milk Nutrition 0.000 description 33
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- QWKWVHKVAFMGCQ-UHFFFAOYSA-N 4,5-dihydroimidazol-1-yl benzoate Chemical class C=1C=CC=CC=1C(=O)ON1CCN=C1 QWKWVHKVAFMGCQ-UHFFFAOYSA-N 0.000 description 11
- 230000002363 herbicidal effect Effects 0.000 description 11
- 235000017168 chlorine Nutrition 0.000 description 10
- 229940060038 chlorine Drugs 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- 229940022682 acetone Drugs 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 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 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 244000075634 Cyperus rotundus Species 0.000 description 4
- 240000006394 Sorghum bicolor Species 0.000 description 4
- 241000209140 Triticum Species 0.000 description 4
- 235000021307 Triticum Nutrition 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000004009 herbicide Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 241001290610 Abildgaardia Species 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 235000007320 Avena fatua Nutrition 0.000 description 3
- 244000075850 Avena orientalis Species 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 244000025254 Cannabis sativa Species 0.000 description 3
- 241000722731 Carex Species 0.000 description 3
- 240000005979 Hordeum vulgare Species 0.000 description 3
- 235000007340 Hordeum vulgare Nutrition 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 239000003570 air Substances 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 3
- 229940050390 benzoate Drugs 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- IRZIRPLBWVYQDJ-UHFFFAOYSA-N 3-methyl-3-propan-2-ylimidazo[1,2-b]isoindole-2,5-dione Chemical compound C1=CC=C2C3=NC(=O)C(C(C)C)(C)N3C(=O)C2=C1 IRZIRPLBWVYQDJ-UHFFFAOYSA-N 0.000 description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
- 240000006995 Abutilon theophrasti Species 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 244000237956 Amaranthus retroflexus Species 0.000 description 2
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 2
- 244000036975 Ambrosia artemisiifolia Species 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- 235000002848 Cyperus flabelliformis Nutrition 0.000 description 2
- 240000001505 Cyperus odoratus Species 0.000 description 2
- 241001110525 Cyperus strigosus Species 0.000 description 2
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- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 2
- 244000058871 Echinochloa crus-galli Species 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 244000299507 Gossypium hirsutum Species 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
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- 240000007594 Oryza sativa Species 0.000 description 2
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- 240000006410 Sida spinosa Species 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 235000007230 Sorghum bicolor Nutrition 0.000 description 2
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
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- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229960000892 attapulgite Drugs 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000009969 flowable effect Effects 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- BMFVGAAISNGQNM-UHFFFAOYSA-N isopentylamine Chemical compound CC(C)CCN BMFVGAAISNGQNM-UHFFFAOYSA-N 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 229910000103 lithium hydride Inorganic materials 0.000 description 2
- 230000036244 malformation Effects 0.000 description 2
- XHFGWHUWQXTGAT-UHFFFAOYSA-N n-methylpropan-2-amine Chemical compound CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 2
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- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
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- 125000001424 substituent group Chemical group 0.000 description 2
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- 231100000167 toxic agent Toxicity 0.000 description 2
- 239000003440 toxic substance Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- LAFRKWDMWGHGPG-UHFFFAOYSA-N 1,3-dioxoisoindole-2-carboxamide Chemical compound C1=CC=C2C(=O)N(C(=O)N)C(=O)C2=C1 LAFRKWDMWGHGPG-UHFFFAOYSA-N 0.000 description 1
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 1
- JPZYXGPCHFZBHO-UHFFFAOYSA-N 1-aminopentadecane Chemical compound CCCCCCCCCCCCCCCN JPZYXGPCHFZBHO-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- RCDZKMLNHXMMRK-UHFFFAOYSA-N 2-(4-cyclohexyl-4-methyl-5-oxo-1h-imidazol-2-yl)-n-prop-2-ynylbenzamide Chemical compound N=1C(=O)C(C)(C2CCCCC2)NC=1C1=CC=CC=C1C(=O)NCC#C RCDZKMLNHXMMRK-UHFFFAOYSA-N 0.000 description 1
- LBYMITLEVJXAQI-UHFFFAOYSA-N 2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)-n,n-diphenylbenzamide Chemical compound O=C1C(C(C)C)(C)NC(C=2C(=CC=CC=2)C(=O)N(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 LBYMITLEVJXAQI-UHFFFAOYSA-N 0.000 description 1
- IWQONEPXLXVQOB-UHFFFAOYSA-N 2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)-n-propan-2-ylbenzamide Chemical compound CC(C)NC(=O)C1=CC=CC=C1C1=NC(C)(C(C)C)C(=O)N1 IWQONEPXLXVQOB-UHFFFAOYSA-N 0.000 description 1
- LJDSTRZHPWMDPG-UHFFFAOYSA-N 2-(butylamino)ethanol Chemical compound CCCCNCCO LJDSTRZHPWMDPG-UHFFFAOYSA-N 0.000 description 1
- GXJQMKFJQFGQKV-KHPPLWFESA-N 2-[methyl-[(z)-octadec-9-enoyl]amino]ethanesulfonic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)N(C)CCS(O)(=O)=O GXJQMKFJQFGQKV-KHPPLWFESA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- IIFFFBSAXDNJHX-UHFFFAOYSA-N 2-methyl-n,n-bis(2-methylpropyl)propan-1-amine Chemical compound CC(C)CN(CC(C)C)CC(C)C IIFFFBSAXDNJHX-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
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- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
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- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BQTTUSNEYLQOEW-UHFFFAOYSA-N prop-2-ynyl 2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)benzoate Chemical compound O=C1C(C(C)C)(C)NC(C=2C(=CC=CC=2)C(=O)OCC#C)=N1 BQTTUSNEYLQOEW-UHFFFAOYSA-N 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
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- 235000009736 ragweed Nutrition 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- IZWPGJFSBABFGL-GMFCBQQYSA-M sodium;2-[methyl-[(z)-octadec-9-enoyl]amino]ethanesulfonate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC(=O)N(C)CCS([O-])(=O)=O IZWPGJFSBABFGL-GMFCBQQYSA-M 0.000 description 1
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- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- QFKMMXYLAPZKIB-UHFFFAOYSA-N undecan-1-amine Chemical compound CCCCCCCCCCCN QFKMMXYLAPZKIB-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
-
- 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
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/70—One oxygen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US82245877A | 1977-08-08 | 1977-08-08 | |
| US822,458 | 1977-08-08 | ||
| US822,459 | 1977-08-08 | ||
| US05/822,459 US4122275A (en) | 1977-08-08 | 1977-08-08 | Imidazolinyl benzamides as herbicidal agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1109878A true CA1109878A (en) | 1981-09-29 |
Family
ID=27124643
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA307,740A Expired CA1109878A (en) | 1977-08-08 | 1978-07-20 | Imidazolinyl benzoic acids esters and salts |
Country Status (24)
| Country | Link |
|---|---|
| JP (1) | JPS5464637A (en, 2012) |
| AR (1) | AR222973A1 (en, 2012) |
| AT (1) | AT364571B (en, 2012) |
| AU (1) | AU518293B2 (en, 2012) |
| BG (1) | BG32411A3 (en, 2012) |
| BR (1) | BR7805062A (en, 2012) |
| CA (1) | CA1109878A (en, 2012) |
| CH (1) | CH639957A5 (en, 2012) |
| CS (1) | CS204033B2 (en, 2012) |
| DD (1) | DD138595A5 (en, 2012) |
| DE (1) | DE2833274A1 (en, 2012) |
| DK (1) | DK157927C (en, 2012) |
| ES (2) | ES472433A1 (en, 2012) |
| FR (1) | FR2400018A1 (en, 2012) |
| GB (1) | GB2004537B (en, 2012) |
| GR (1) | GR72789B (en, 2012) |
| HU (1) | HU181841B (en, 2012) |
| IL (1) | IL55064A (en, 2012) |
| IT (1) | IT1107482B (en, 2012) |
| NL (1) | NL7808228A (en, 2012) |
| NZ (1) | NZ187812A (en, 2012) |
| SE (1) | SE448729B (en, 2012) |
| UA (1) | UA6015A1 (en, 2012) |
| YU (2) | YU41316B (en, 2012) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3474020D1 (en) * | 1983-08-02 | 1988-10-20 | American Cyanamid Co | Imidazolidinones, and imidazolidinethiones, process for the preparation thereof, and use of said compounds as herbicidal agents |
| EP0133311A3 (en) * | 1983-08-02 | 1987-12-23 | American Cyanamid Company | Substituted imidazolinyl benzoic acids, esters and salts and use thereof as herbicidal agents |
| DE3340595A1 (de) * | 1983-11-10 | 1985-05-23 | Hoechst Ag, 6230 Frankfurt | Imidazolinone, verfahren zu ihrer herstellung und ihre verwendung im pflanzenschutz |
| DE3340594A1 (de) * | 1983-11-10 | 1985-05-23 | Hoechst Ag, 6230 Frankfurt | 2-arylsubstituierte imidazolinone, verfahren zu ihrer herstellung und ihre verwendung im pflanzenschutz |
| DE3345901A1 (de) * | 1983-12-20 | 1985-06-27 | Hoechst Ag, 6230 Frankfurt | 1-acylimidazolinone, verfahren zu ihrer herstellung und ihre verwendung in der landwirtschaft |
| ATE64597T1 (de) * | 1984-02-10 | 1991-07-15 | American Cyanamid Co | Regio und optische isomere von imidazolinyltoluols|ure, deren ester und salze, verfahren zu deren herstellung und deren anwendung als herbizide. |
| GB8507808D0 (en) * | 1985-03-26 | 1985-05-01 | Shell Int Research | Heterocyclic herbicides |
| US4726835A (en) * | 1985-12-02 | 1988-02-23 | Idemitsu Kosan Company Limited | Herbicidal and plant growth regulating imidazoline derivatives |
| EP0412577A1 (de) | 1986-05-09 | 1991-02-13 | Hoechst Aktiengesellschaft | Herbizide Mittel |
| US4895588A (en) * | 1987-07-01 | 1990-01-23 | Ciba-Geigy Corporation | Substituted imidazolones having herbicidal activity |
| DE3938564A1 (de) * | 1989-11-21 | 1991-05-23 | Hoechst Ag | Herbizide mittel |
| US5525578A (en) * | 1989-11-21 | 1996-06-11 | Hoechst Aktiengesellschaft | Herbicidal agents containing imidazole herbicide and ether sulfate surfactants |
| 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 |
| US8367669B2 (en) | 2005-06-15 | 2013-02-05 | Vanderbilt University | Inhibitors of hemeprotein-catalyzed lipid peroxidation |
| US9133212B1 (en) | 2005-06-15 | 2015-09-15 | Vanderbilt University | Inhibitors of hemeprotein-catalyzed lipid peroxidation |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1176660B (de) * | 1963-07-05 | 1964-08-27 | Beiersdorf & Co A G P | Verfahren zur Herstellung von triaryl-substituierten Imidazolinonen-4(5) |
| US3645965A (en) * | 1967-10-23 | 1972-02-29 | Sankyo Co | Stabilization of synthetic polymers with imidazolidine compounds |
| US3687971A (en) * | 1970-06-22 | 1972-08-29 | Merck & Co Inc | 4-(pyrrolyl)-salicylic acid derivatives |
-
1978
- 1978-07-03 IL IL55064A patent/IL55064A/xx active IP Right Grant
- 1978-07-07 AU AU37867/78A patent/AU518293B2/en not_active Expired
- 1978-07-07 GR GR56732A patent/GR72789B/el unknown
- 1978-07-10 NZ NZ187812A patent/NZ187812A/xx unknown
- 1978-07-17 AR AR272981A patent/AR222973A1/es active
- 1978-07-20 CA CA307,740A patent/CA1109878A/en not_active Expired
- 1978-07-24 YU YU1758/78A patent/YU41316B/xx unknown
- 1978-07-25 IT IT50457/78A patent/IT1107482B/it active Protection Beyond IP Right Term
- 1978-07-26 GB GB7831112A patent/GB2004537B/en not_active Expired
- 1978-07-28 DE DE19782833274 patent/DE2833274A1/de active Granted
- 1978-08-03 CH CH828978A patent/CH639957A5/de not_active IP Right Cessation
- 1978-08-04 NL NL787808228A patent/NL7808228A/xx unknown
- 1978-08-07 SE SE7808451A patent/SE448729B/sv not_active IP Right Cessation
- 1978-08-07 BR BR7805062A patent/BR7805062A/pt unknown
- 1978-08-07 DK DK348278A patent/DK157927C/da not_active IP Right Cessation
- 1978-08-07 BG BG040610A patent/BG32411A3/xx unknown
- 1978-08-08 ES ES472433A patent/ES472433A1/es not_active Expired
- 1978-08-08 DD DD78207175A patent/DD138595A5/xx not_active IP Right Cessation
- 1978-08-08 UA UA2646369A patent/UA6015A1/uk unknown
- 1978-08-08 CS CS785182A patent/CS204033B2/cs unknown
- 1978-08-08 JP JP9658178A patent/JPS5464637A/ja active Granted
- 1978-08-08 HU HU78AE540A patent/HU181841B/hu unknown
- 1978-08-08 FR FR7823383A patent/FR2400018A1/fr active Granted
- 1978-08-08 AT AT0577478A patent/AT364571B/de active
-
1979
- 1979-04-10 ES ES479467A patent/ES479467A1/es not_active Expired
-
1982
- 1982-10-07 YU YU2255/82A patent/YU40967B/xx unknown
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