CS38891A2 - New benzin oxazole derivatives, method of their production,their application and respective herbicides - Google Patents

Info

Publication number

CS38891A2

CS38891A2 CS91388A CS38891A CS38891A2 CS 38891 A2 CS38891 A2 CS 38891A2 CS 91388 A CS91388 A CS 91388A CS 38891 A CS38891 A CS 38891A CS 38891 A2 CS38891 A2 CS 38891A2

Authority

CS

Czechoslovakia

Prior art keywords

compound

cpi

group

formula

mixture

Prior art date

1990-02-16

Links

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• 238000000034 method Methods 0.000 title claims abstract description 10
• 239000004009 herbicide Substances 0.000 title claims description 34
• -1 benzin oxazole derivatives Chemical class 0.000 title description 59
• 238000004519 manufacturing process Methods 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 288
• 239000000203 mixture Substances 0.000 claims abstract description 155
• 238000002360 preparation method Methods 0.000 claims abstract description 58
• 125000003118 aryl group Chemical group 0.000 claims abstract description 18
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 14
• 125000000304 alkynyl group Chemical group 0.000 claims abstract description 14
• 230000002363 herbicidal effect Effects 0.000 claims abstract description 14
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 12
• 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 12
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
• 150000002367 halogens Chemical class 0.000 claims abstract description 9
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 5
• 150000001768 cations Chemical class 0.000 claims abstract description 5
• 125000005017 substituted alkenyl group Chemical group 0.000 claims abstract 2
• 238000006243 chemical reaction Methods 0.000 claims description 27
• 229910052739 hydrogen Inorganic materials 0.000 claims description 23
• 239000001257 hydrogen Substances 0.000 claims description 22
• 150000002148 esters Chemical class 0.000 claims description 18
• 150000003839 salts Chemical class 0.000 claims description 18
• 229910052757 nitrogen Inorganic materials 0.000 claims description 17
• 125000004432 carbon atom Chemical group C* 0.000 claims description 16
• 239000002253 acid Substances 0.000 claims description 14
• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims description 12
• 150000001408 amides Chemical class 0.000 claims description 12
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
• 150000002431 hydrogen Chemical class 0.000 claims description 8
• 229910052760 oxygen Inorganic materials 0.000 claims description 7
• 125000001424 substituent group Chemical group 0.000 claims description 7
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
• 125000004429 atom Chemical group 0.000 claims description 5
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
• 239000003085 diluting agent Substances 0.000 claims description 5
• 239000001301 oxygen Substances 0.000 claims description 5
• 125000003368 amide group Chemical group 0.000 claims description 4
• 230000015572 biosynthetic process Effects 0.000 claims description 4
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical class NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 3
• 150000008316 benzisoxazoles Chemical class 0.000 claims description 3
• 230000012010 growth Effects 0.000 claims description 3
• 230000003647 oxidation Effects 0.000 claims description 3
• 238000007254 oxidation reaction Methods 0.000 claims description 3
• 125000004076 pyridyl group Chemical group 0.000 claims description 3
• 230000001476 alcoholic effect Effects 0.000 claims description 2
• 230000029936 alkylation Effects 0.000 claims description 2
• 238000005804 alkylation reaction Methods 0.000 claims description 2
• 230000032050 esterification Effects 0.000 claims description 2
• 238000005886 esterification reaction Methods 0.000 claims description 2
• 230000007062 hydrolysis Effects 0.000 claims description 2
• 238000006460 hydrolysis reaction Methods 0.000 claims description 2
• 150000002825 nitriles Chemical class 0.000 claims description 2
• 125000003107 substituted aryl group Chemical group 0.000 claims description 2
• 229940124530 sulfonamide Drugs 0.000 claims description 2
• 150000003456 sulfonamides Chemical class 0.000 claims description 2
• 150000001298 alcohols Chemical class 0.000 claims 1
• 230000018044 dehydration Effects 0.000 claims 1
• 238000006297 dehydration reaction Methods 0.000 claims 1
• AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims 1
• 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
• 125000004430 oxygen atom Chemical group O* 0.000 claims 1
• 125000003226 pyrazolyl group Chemical group 0.000 claims 1
• 150000001450 anions Chemical class 0.000 abstract description 2
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
• 125000006355 carbonyl methylene group Chemical group [H]C([H])([*:2])C([*:1])=O 0.000 abstract 1
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 296
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 117
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 117
• 239000000243 solution Substances 0.000 description 110
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 106
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 82
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 80
• 239000007787 solid Substances 0.000 description 72
• 101150059231 CPI1 gene Proteins 0.000 description 67
• 125000001309 chloro group Chemical group Cl* 0.000 description 63
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 54
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 53
• 239000011541 reaction mixture Substances 0.000 description 52
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 51
• 101100138673 Arabidopsis thaliana NPF3.1 gene Proteins 0.000 description 50
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
• 239000000460 chlorine Substances 0.000 description 44
• 239000012267 brine Substances 0.000 description 42
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 42
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 40
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 38
• 239000000377 silicon dioxide Substances 0.000 description 37
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 34
• 239000012259 ether extract Substances 0.000 description 34
• 238000012746 preparative thin layer chromatography Methods 0.000 description 31
• 239000003921 oil Substances 0.000 description 30
• 239000013256 coordination polymer Substances 0.000 description 29
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
• 238000001816 cooling Methods 0.000 description 27
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 26
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
• 238000010992 reflux Methods 0.000 description 23
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 22
• 239000002585 base Substances 0.000 description 22
• 239000007858 starting material Substances 0.000 description 22
• 239000002244 precipitate Substances 0.000 description 20
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
• 235000019439 ethyl acetate Nutrition 0.000 description 18
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
• 239000002904 solvent Substances 0.000 description 16
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 14
• 239000004480 active ingredient Substances 0.000 description 14
• 241000196324 Embryophyta Species 0.000 description 13
• 229960001760 dimethyl sulfoxide Drugs 0.000 description 13
• 239000000706 filtrate Substances 0.000 description 13
• 238000003756 stirring Methods 0.000 description 13
• 239000000725 suspension Substances 0.000 description 13
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 12
• 239000000463 material Substances 0.000 description 12
• 238000005406 washing Methods 0.000 description 12
• 239000007864 aqueous solution Substances 0.000 description 11
• 239000003960 organic solvent Substances 0.000 description 11
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
• 235000017557 sodium bicarbonate Nutrition 0.000 description 11
• 239000000126 substance Substances 0.000 description 11
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 11
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 10
• 230000003197 catalytic effect Effects 0.000 description 10
• 239000000284 extract Substances 0.000 description 10
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
• 101100515517 Arabidopsis thaliana XI-I gene Proteins 0.000 description 9
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 9
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
• 235000011054 acetic acid Nutrition 0.000 description 9
• 229960000583 acetic acid Drugs 0.000 description 9
• 235000011089 carbon dioxide Nutrition 0.000 description 9
• 239000004094 surface-active agent Substances 0.000 description 9
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 8
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
• 235000019341 magnesium sulphate Nutrition 0.000 description 8
• 239000011591 potassium Substances 0.000 description 8
• 229910000027 potassium carbonate Inorganic materials 0.000 description 8
• 238000005507 spraying Methods 0.000 description 8
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
• 229940086542 triethylamine Drugs 0.000 description 8
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
• 229910052801 chlorine Inorganic materials 0.000 description 7
• 239000012141 concentrate Substances 0.000 description 7
• 125000004093 cyano group Chemical group *C#N 0.000 description 7
• 229910052700 potassium Inorganic materials 0.000 description 7
• 239000000741 silica gel Substances 0.000 description 7
• 229910002027 silica gel Inorganic materials 0.000 description 7
• 239000011734 sodium Substances 0.000 description 7
• 229910000104 sodium hydride Inorganic materials 0.000 description 7
• 239000012312 sodium hydride Substances 0.000 description 7
• 238000004809 thin layer chromatography Methods 0.000 description 7
• VNDWQCSOSCCWIP-UHFFFAOYSA-N 2-tert-butyl-9-fluoro-1,6-dihydrobenzo[h]imidazo[4,5-f]isoquinolin-7-one Chemical compound C1=2C=CNC(=O)C=2C2=CC(F)=CC=C2C2=C1NC(C(C)(C)C)=N2 VNDWQCSOSCCWIP-UHFFFAOYSA-N 0.000 description 6
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
• KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 6
• 101150041968 CDC13 gene Proteins 0.000 description 6
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
• 150000001263 acyl chlorides Chemical class 0.000 description 6
• 229910002092 carbon dioxide Inorganic materials 0.000 description 6
• 238000001914 filtration Methods 0.000 description 6
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
• 229910052794 bromium Inorganic materials 0.000 description 5
• 238000003818 flash chromatography Methods 0.000 description 5
• 238000009472 formulation Methods 0.000 description 5
• 229910052740 iodine Inorganic materials 0.000 description 5
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
• 229920005989 resin Polymers 0.000 description 5
• 239000011347 resin Substances 0.000 description 5
• 239000007921 spray Substances 0.000 description 5
• 239000003381 stabilizer Substances 0.000 description 5
• CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 4
• WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 4
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
• IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
• 125000003545 alkoxy group Chemical group 0.000 description 4
• VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical group Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
• 125000001246 bromo group Chemical group Br* 0.000 description 4
• 239000003795 chemical substances by application Substances 0.000 description 4
• 238000004587 chromatography analysis Methods 0.000 description 4
• 239000012230 colorless oil Substances 0.000 description 4
• 238000004440 column chromatography Methods 0.000 description 4
• 238000000354 decomposition reaction Methods 0.000 description 4
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
• 239000006185 dispersion Substances 0.000 description 4
• 239000011737 fluorine Substances 0.000 description 4
• 229910052731 fluorine Inorganic materials 0.000 description 4
• 125000001153 fluoro group Chemical group F* 0.000 description 4
• 239000002917 insecticide Substances 0.000 description 4
• 238000002844 melting Methods 0.000 description 4
• 230000008018 melting Effects 0.000 description 4
• PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 4
• 150000002828 nitro derivatives Chemical class 0.000 description 4
• 229910052708 sodium Inorganic materials 0.000 description 4
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical group [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
• 239000010936 titanium Substances 0.000 description 4
• 238000001665 trituration Methods 0.000 description 4
• SQBFKIHOMAMLEJ-UHFFFAOYSA-N 2-[2-[2-[2-[bis(carboxymethyl)amino]-5-[hydroxy-(6-nitro-1,3-benzodioxol-5-yl)methyl]phenoxy]ethoxy]-n-(carboxymethyl)-4-methylanilino]acetic acid Chemical compound CC1=CC=C(N(CC(O)=O)CC(O)=O)C(OCCOC=2C(=CC=C(C=2)C(O)C=2C(=CC=3OCOC=3C=2)[N+]([O-])=O)N(CC(O)=O)CC(O)=O)=C1 SQBFKIHOMAMLEJ-UHFFFAOYSA-N 0.000 description 3
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
• WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
• 101100153505 Caenorhabditis elegans tni-1 gene Proteins 0.000 description 3
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
• 229910001854 alkali hydroxide Inorganic materials 0.000 description 3
• 229910052783 alkali metal Inorganic materials 0.000 description 3
• 229910000288 alkali metal carbonate Inorganic materials 0.000 description 3
• 150000008041 alkali metal carbonates Chemical class 0.000 description 3
• 239000000908 ammonium hydroxide Substances 0.000 description 3
• 239000011575 calcium Substances 0.000 description 3
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• 238000012512 characterization method Methods 0.000 description 3
• 229940126214 compound 3 Drugs 0.000 description 3
• BERDEBHAJNAUOM-UHFFFAOYSA-N copper(i) oxide Chemical compound [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 3
• 239000012043 crude product Substances 0.000 description 3
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
• 125000001188 haloalkyl group Chemical group 0.000 description 3
• 125000005843 halogen group Chemical group 0.000 description 3
• 150000004679 hydroxides Chemical class 0.000 description 3
• 150000002576 ketones Chemical class 0.000 description 3
• 230000002147 killing effect Effects 0.000 description 3
• 239000007788 liquid Substances 0.000 description 3
• 150000004702 methyl esters Chemical class 0.000 description 3
• 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 3
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
• 239000003208 petroleum Substances 0.000 description 3
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• 239000000047 product Substances 0.000 description 3
• 238000000746 purification Methods 0.000 description 3
• 241000894007 species Species 0.000 description 3
• RHUYHJGZWVXEHW-UHFFFAOYSA-N 1,1-Dimethyhydrazine Chemical compound CN(C)N RHUYHJGZWVXEHW-UHFFFAOYSA-N 0.000 description 2
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
• VPAGKEZJDCSVOW-UHFFFAOYSA-N 1-(5-fluoro-2-nitrophenyl)ethanone Chemical compound CC(=O)C1=CC(F)=CC=C1[N+]([O-])=O VPAGKEZJDCSVOW-UHFFFAOYSA-N 0.000 description 2
• YIVXMZJTEQBPQO-UHFFFAOYSA-N 2,4-DB Chemical compound OC(=O)CCCOC1=CC=C(Cl)C=C1Cl YIVXMZJTEQBPQO-UHFFFAOYSA-N 0.000 description 2
• 239000002794 2,4-DB Substances 0.000 description 2
• YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-UHFFFAOYSA-N 0.000 description 2
• WNTGYJSOUMFZEP-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 description 2
• HBALLWSUQCOFSN-UHFFFAOYSA-N 2-(5-hydroxy-1,2-benzoxazol-3-yl)acetic acid Chemical compound C1=C(O)C=C2C(CC(=O)O)=NOC2=C1 HBALLWSUQCOFSN-UHFFFAOYSA-N 0.000 description 2
• XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 2
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