CS204033B2 - Herbicide means - Google Patents
Herbicide means Download PDFInfo
- Publication number
- CS204033B2 CS204033B2 CS785182A CS518278A CS204033B2 CS 204033 B2 CS204033 B2 CS 204033B2 CS 785182 A CS785182 A CS 785182A CS 518278 A CS518278 A CS 518278A CS 204033 B2 CS204033 B2 CS 204033B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- group
- alkyl
- carbon atoms
- methyl
- optionally substituted
- Prior art date
Links
- 230000002363 herbicidal effect Effects 0.000 title claims description 34
- 239000004009 herbicide Substances 0.000 title abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 51
- 239000000203 mixture Substances 0.000 claims abstract description 41
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 40
- 150000003839 salts Chemical class 0.000 claims abstract description 35
- -1 cyclohexenylmethyl Chemical group 0.000 claims abstract description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 32
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 32
- 239000001257 hydrogen Substances 0.000 claims abstract description 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 25
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 22
- 150000002367 halogens Chemical class 0.000 claims abstract description 21
- 239000002253 acid Substances 0.000 claims abstract description 20
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 20
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 19
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 19
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 18
- 150000001768 cations Chemical class 0.000 claims abstract description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 16
- 230000003287 optical effect Effects 0.000 claims abstract description 12
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 9
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 8
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 8
- 239000000460 chlorine Substances 0.000 claims abstract description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
- 125000002541 furyl group Chemical group 0.000 claims abstract description 6
- 125000005059 halophenyl group Chemical group 0.000 claims abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 57
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
- 239000004480 active ingredient Substances 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 18
- 239000011541 reaction mixture Substances 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 12
- 150000001721 carbon Chemical group 0.000 claims description 10
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims description 8
- 150000008046 alkali metal hydrides Chemical class 0.000 claims description 8
- 239000000010 aprotic solvent Substances 0.000 claims description 8
- 239000012298 atmosphere Substances 0.000 claims description 7
- 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 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 6
- 239000011261 inert gas Substances 0.000 claims description 5
- RCVABMZVLZNJAG-UHFFFAOYSA-N 2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)benzoic acid Chemical group N1C(=O)C(C(C)C)(C)N=C1C1=CC=CC=C1C(O)=O RCVABMZVLZNJAG-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 3
- 239000007789 gas Substances 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- XXZXLDWHTQEUKD-UHFFFAOYSA-N ethyl 2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)benzoate Chemical group CCOC(=O)C1=CC=CC=C1C1=NC(C)(C(C)C)C(=O)N1 XXZXLDWHTQEUKD-UHFFFAOYSA-N 0.000 claims 1
- HBEIBCGCAXFZAX-UHFFFAOYSA-N methyl 2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)benzoate Chemical group COC(=O)C1=CC=CC=C1C1=NC(C)(C(C)C)C(=O)N1 HBEIBCGCAXFZAX-UHFFFAOYSA-N 0.000 claims 1
- CPXCDEMFNPKOEF-UHFFFAOYSA-N methyl 3-methylbenzoate Chemical compound COC(=O)C1=CC=CC(C)=C1 CPXCDEMFNPKOEF-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 abstract description 11
- 230000000694 effects Effects 0.000 abstract description 9
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 125000001424 substituent group Chemical group 0.000 abstract description 2
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 description 26
- 239000000243 solution Substances 0.000 description 16
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 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 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 101000986989 Naja kaouthia Acidic phospholipase A2 CM-II Proteins 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 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
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 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 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 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 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 235000007320 Avena fatua Nutrition 0.000 description 3
- 241000209764 Avena fatua Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 239000005995 Aluminium silicate Substances 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
- 241000234653 Cyperus Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000209510 Liliopsida Species 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 229920001213 Polysorbate 20 Polymers 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
- 240000006394 Sorghum bicolor Species 0.000 description 2
- 235000007230 Sorghum bicolor Nutrition 0.000 description 2
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 2
- 244000062793 Sorghum vulgare Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 241001148683 Zostera marina Species 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 229960000892 attapulgite Drugs 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 241001233957 eudicotyledons Species 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000000227 grinding Methods 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
- 239000003921 oil Substances 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 229910052625 palygorskite Inorganic materials 0.000 description 2
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229920005552 sodium lignosulfonate Polymers 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000004094 surface-active agent Substances 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
- ANFXTILBDGTSEG-UHFFFAOYSA-N 1-methyl-4,5-dihydroimidazole Chemical compound CN1CCN=C1 ANFXTILBDGTSEG-UHFFFAOYSA-N 0.000 description 1
- HHCYLDWTHIPYMV-UHFFFAOYSA-N 2-(4,5-dihydro-1h-imidazol-2-yl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=NCCN1 HHCYLDWTHIPYMV-UHFFFAOYSA-N 0.000 description 1
- HQUZQJGGHDJRBK-UHFFFAOYSA-N 2-(4,5-dihydroimidazol-1-yl)benzamide Chemical class NC(=O)C1=CC=CC=C1N1C=NCC1 HQUZQJGGHDJRBK-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 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 1
- 101710187795 60S ribosomal protein L15 Proteins 0.000 description 1
- 241000219144 Abutilon Species 0.000 description 1
- 244000237956 Amaranthus retroflexus Species 0.000 description 1
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 1
- 244000036975 Ambrosia artemisiifolia Species 0.000 description 1
- 235000003133 Ambrosia artemisiifolia Nutrition 0.000 description 1
- 244000024671 Brassica kaber Species 0.000 description 1
- 235000014750 Brassica kaber Nutrition 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 description 1
- 101100386518 Caenorhabditis elegans dbl-1 gene Proteins 0.000 description 1
- 241000234646 Cyperaceae Species 0.000 description 1
- 244000099162 Cyperus alternifolius Species 0.000 description 1
- 244000075634 Cyperus rotundus Species 0.000 description 1
- 241001110525 Cyperus strigosus Species 0.000 description 1
- 240000008853 Datura stramonium Species 0.000 description 1
- 244000152970 Digitaria sanguinalis Species 0.000 description 1
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- XNPOFXIBHOVFFH-UHFFFAOYSA-N N-cyclohexyl-N'-(2-(4-morpholinyl)ethyl)carbodiimide Chemical compound C1CCCCC1N=C=NCCN1CCOCC1 XNPOFXIBHOVFFH-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 244000088461 Panicum crus-galli Species 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000533293 Sesbania emerus Species 0.000 description 1
- 240000003461 Setaria viridis Species 0.000 description 1
- 235000002248 Setaria viridis Nutrition 0.000 description 1
- 240000006410 Sida spinosa Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 235000007244 Zea mays Nutrition 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 1
- 208000006278 hypochromic anemia Diseases 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical class CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000008654 plant damage Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical group OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 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
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- NVZLBPXTJTXPDC-UHFFFAOYSA-N pyrrolo[3,4-e]benzimidazole Chemical compound C1=CC2=NC=NC2=C2C=NC=C21 NVZLBPXTJTXPDC-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002594 sorbent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US82245877A | 1977-08-08 | 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 |
|---|---|
| CS204033B2 true CS204033B2 (en) | 1981-03-31 |
Family
ID=27124643
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS785182A CS204033B2 (en) | 1977-08-08 | 1978-08-08 | Herbicide means |
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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