JPH0536439B2 - - Google Patents

Info

Publication number

JPH0536439B2

JPH0536439B2 JP62056250A JP5625087A JPH0536439B2 JP H0536439 B2 JPH0536439 B2 JP H0536439B2 JP 62056250 A JP62056250 A JP 62056250A JP 5625087 A JP5625087 A JP 5625087A JP H0536439 B2 JPH0536439 B2 JP H0536439B2

Authority

JP

Japan

Prior art keywords

group

formula

compound

salt

reaction

Prior art date

1986-03-20

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 - Lifetime

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• 150000001875 compounds Chemical class 0.000 claims description 212
• 150000003839 salts Chemical class 0.000 claims description 98
• 125000000623 heterocyclic group Chemical group 0.000 claims description 55
• 125000000217 alkyl group Chemical group 0.000 claims description 36
• 125000005843 halogen group Chemical group 0.000 claims description 28
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 28
• 230000002363 herbicidal effect Effects 0.000 claims description 27
• 125000003545 alkoxy group Chemical group 0.000 claims description 24
• 229910052717 sulfur Inorganic materials 0.000 claims description 19
• 125000001424 substituent group Chemical group 0.000 claims description 18
• 239000004009 herbicide Substances 0.000 claims description 15
• 229910052799 carbon Inorganic materials 0.000 claims description 11
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
• 125000003277 amino group Chemical group 0.000 claims description 9
• 125000004429 atom Chemical group 0.000 claims description 7
• 238000004519 manufacturing process Methods 0.000 claims description 7
• 229910052760 oxygen Inorganic materials 0.000 claims description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
• 239000001257 hydrogen Substances 0.000 claims description 3
• 229910052739 hydrogen Inorganic materials 0.000 claims description 3
• -1 heterocyclic sulfonylurea derivative Chemical class 0.000 description 209
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 136
• 238000006243 chemical reaction Methods 0.000 description 111
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 98
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 93
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 80
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 67
• 125000004432 carbon atom Chemical group C* 0.000 description 63
• 239000013078 crystal Substances 0.000 description 63
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 61
• 238000003756 stirring Methods 0.000 description 57
• 239000000243 solution Substances 0.000 description 50
• 238000001816 cooling Methods 0.000 description 42
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 40
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
• 239000000203 mixture Substances 0.000 description 39
• 238000001914 filtration Methods 0.000 description 38
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 35
• 238000000034 method Methods 0.000 description 34
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
• 238000010898 silica gel chromatography Methods 0.000 description 30
• 238000010992 reflux Methods 0.000 description 26
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 24
• 239000002244 precipitate Substances 0.000 description 23
• 239000002904 solvent Substances 0.000 description 22
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
• 125000002252 acyl group Chemical group 0.000 description 20
• 239000002585 base Substances 0.000 description 20
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 20
• 239000003795 chemical substances by application Substances 0.000 description 19
• 239000005457 ice water Substances 0.000 description 19
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 18
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
• 239000003480 eluent Substances 0.000 description 17
• 239000003921 oil Substances 0.000 description 17
• 240000007594 Oryza sativa Species 0.000 description 16
• 235000007164 Oryza sativa Nutrition 0.000 description 16
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 16
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 16
• 235000009566 rice Nutrition 0.000 description 16
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
• 239000010410 layer Substances 0.000 description 15
• JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 14
• 239000000460 chlorine Substances 0.000 description 14
• KJYKABTWCXRMTA-UHFFFAOYSA-N phenyl n-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamate Chemical compound COC1=NC(C)=NC(NC(=O)OC=2C=CC=CC=2)=N1 KJYKABTWCXRMTA-UHFFFAOYSA-N 0.000 description 14
• 125000004434 sulfur atom Chemical group 0.000 description 14
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 14
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 13
• 241000196324 Embryophyta Species 0.000 description 13
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
• 125000004414 alkyl thio group Chemical group 0.000 description 13
• 239000008187 granular material Substances 0.000 description 13
• 150000002430 hydrocarbons Chemical group 0.000 description 13
• 229910052757 nitrogen Inorganic materials 0.000 description 13
• 229940124530 sulfonamide Drugs 0.000 description 13
• RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 13
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 12
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
• 125000003118 aryl group Chemical group 0.000 description 12
• 229910052801 chlorine Inorganic materials 0.000 description 12
• 239000012156 elution solvent Substances 0.000 description 12
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
• 239000000126 substance Substances 0.000 description 12
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 11
• 235000011114 ammonium hydroxide Nutrition 0.000 description 11
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 10
• 239000002253 acid Substances 0.000 description 10
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
• 239000000843 powder Substances 0.000 description 10
• 239000012312 sodium hydride Substances 0.000 description 10
• 229910000104 sodium hydride Inorganic materials 0.000 description 10
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 9
• 229910052794 bromium Inorganic materials 0.000 description 9
• 125000004122 cyclic group Chemical group 0.000 description 9
• 239000000706 filtrate Substances 0.000 description 9
• 125000004430 oxygen atom Chemical group O* 0.000 description 9
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 8
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 8
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
• 230000002378 acidificating effect Effects 0.000 description 8
• 125000003342 alkenyl group Chemical group 0.000 description 8
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 8
• 125000003282 alkyl amino group Chemical group 0.000 description 8
• 239000011737 fluorine Substances 0.000 description 8
• 229910052731 fluorine Inorganic materials 0.000 description 8
• 238000009472 formulation Methods 0.000 description 8
• 230000035484 reaction time Effects 0.000 description 8
• 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 description 7
• 244000301850 Cupressus sempervirens Species 0.000 description 7
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 7
• 239000012141 concentrate Substances 0.000 description 7
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
• YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 7
• XBLVHTDFJBKJLG-UHFFFAOYSA-N Ethyl nicotinate Chemical compound CCOC(=O)C1=CC=CN=C1 XBLVHTDFJBKJLG-UHFFFAOYSA-N 0.000 description 6
• 231100000674 Phytotoxicity Toxicity 0.000 description 6
• 230000002411 adverse Effects 0.000 description 6
• 125000000304 alkynyl group Chemical group 0.000 description 6
• 238000001035 drying Methods 0.000 description 6
• DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 6
• 230000002140 halogenating effect Effects 0.000 description 6
• 150000002391 heterocyclic compounds Chemical class 0.000 description 6
• 229910000027 potassium carbonate Inorganic materials 0.000 description 6
• 239000002689 soil Substances 0.000 description 6
• 239000007787 solid Substances 0.000 description 6
• 244000025254 Cannabis sativa Species 0.000 description 5
• 244000068988 Glycine max Species 0.000 description 5
• 235000010469 Glycine max Nutrition 0.000 description 5
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 5
• 241000209140 Triticum Species 0.000 description 5
• 235000021307 Triticum Nutrition 0.000 description 5
• 125000005137 alkenylsulfonyl group Chemical group 0.000 description 5
• 125000005108 alkenylthio group Chemical group 0.000 description 5
• 125000004644 alkyl sulfinyl group Chemical group 0.000 description 5
• 229910021529 ammonia Inorganic materials 0.000 description 5
• 125000003710 aryl alkyl group Chemical group 0.000 description 5
• 125000005135 aryl sulfinyl group Chemical group 0.000 description 5
• 239000000440 bentonite Substances 0.000 description 5
• 229910000278 bentonite Inorganic materials 0.000 description 5
• SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 5
• 125000004093 cyano group Chemical group *C#N 0.000 description 5
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
• YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 5
• 239000000839 emulsion Substances 0.000 description 5
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
• 150000007522 mineralic acids Chemical class 0.000 description 5
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
• 150000007524 organic acids Chemical class 0.000 description 5
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
• 239000002994 raw material Substances 0.000 description 5
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 5
• SKFNUROCOVAKFR-UHFFFAOYSA-N 2-chloroimidazo[1,2-a]pyridine-3-sulfonyl chloride Chemical compound C1=CC=CN2C(S(Cl)(=O)=O)=C(Cl)N=C21 SKFNUROCOVAKFR-UHFFFAOYSA-N 0.000 description 4
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 4
• RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 4
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
• 240000005979 Hordeum vulgare Species 0.000 description 4
• 235000007340 Hordeum vulgare Nutrition 0.000 description 4
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
• 241001076438 Oxya japonica Species 0.000 description 4
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
• 240000008042 Zea mays Species 0.000 description 4
• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 4
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 4
• 125000004423 acyloxy group Chemical group 0.000 description 4
• 125000003302 alkenyloxy group Chemical group 0.000 description 4
• 125000005136 alkenylsulfinyl group Chemical group 0.000 description 4
• VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 4
• 239000007864 aqueous solution Substances 0.000 description 4
• 125000005140 aralkylsulfonyl group Chemical group 0.000 description 4
• 125000005099 aryl alkyl carbonyl group Chemical group 0.000 description 4
• 125000004659 aryl alkyl thio group Chemical group 0.000 description 4
• 125000002102 aryl alkyloxo group Chemical group 0.000 description 4
• 125000005129 aryl carbonyl group Chemical group 0.000 description 4
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 4
• 125000004391 aryl sulfonyl group Chemical group 0.000 description 4
• 125000005110 aryl thio group Chemical group 0.000 description 4
• 125000004104 aryloxy group Chemical group 0.000 description 4
• 150000001721 carbon Chemical group 0.000 description 4
• 239000004927 clay Substances 0.000 description 4
• 235000005822 corn Nutrition 0.000 description 4
• 238000000354 decomposition reaction Methods 0.000 description 4
• 239000012954 diazonium Substances 0.000 description 4
• 150000001989 diazonium salts Chemical class 0.000 description 4
• 150000002170 ethers Chemical class 0.000 description 4
• OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 4
• 235000013312 flour Nutrition 0.000 description 4
• 239000000417 fungicide Substances 0.000 description 4
• 150000008282 halocarbons Chemical class 0.000 description 4
• 125000005842 heteroatom Chemical group 0.000 description 4
• 239000002198 insoluble material Substances 0.000 description 4
• 239000007788 liquid Substances 0.000 description 4
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
• LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
• 239000007800 oxidant agent Substances 0.000 description 4
• NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
• 238000001953 recrystallisation Methods 0.000 description 4
• 125000006413 ring segment Chemical group 0.000 description 4
• 229910000029 sodium carbonate Inorganic materials 0.000 description 4
• 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 4
• 150000003456 sulfonamides Chemical class 0.000 description 4
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
• 238000005406 washing Methods 0.000 description 4
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 3
• KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 3
• LBCREEUWXFNSAC-UHFFFAOYSA-N 2-(chloromethyl)imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC(CCl)=CN21 LBCREEUWXFNSAC-UHFFFAOYSA-N 0.000 description 3
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
• LVFRCHIUUKWBLR-UHFFFAOYSA-N 4,6-dimethoxypyrimidin-2-amine Chemical compound COC1=CC(OC)=NC(N)=N1 LVFRCHIUUKWBLR-UHFFFAOYSA-N 0.000 description 3
• 241000251468 Actinopterygii Species 0.000 description 3
• QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
• ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
• NAGRVUXEKKZNHT-UHFFFAOYSA-N Imazosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2N3C=CC=CC3=NC=2Cl)=N1 NAGRVUXEKKZNHT-UHFFFAOYSA-N 0.000 description 3
• 241000124008 Mammalia Species 0.000 description 3
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
• 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
• 235000011684 Sorghum saccharatum Nutrition 0.000 description 3
• 244000062793 Sorghum vulgare Species 0.000 description 3
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
• 125000004442 acylamino group Chemical group 0.000 description 3
• 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 3
• 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
• 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 3
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• XHMVOKRMSDGGNG-UHFFFAOYSA-N ethyl 3-methyl-7-sulfamoylpyrazolo[5,1-b][1,3]thiazole-6-carboxylate Chemical compound CC1=CSC2=C(S(N)(=O)=O)C(C(=O)OCC)=NN21 XHMVOKRMSDGGNG-UHFFFAOYSA-N 0.000 description 1
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• ZXDBTXLCCSXSBD-UHFFFAOYSA-N methyl 7-[(6-methoxycarbonyl-3-methylpyrazolo[5,1-b][1,3]thiazol-7-yl)disulfanyl]-3-methylpyrazolo[5,1-b][1,3]thiazole-6-carboxylate Chemical compound COC(=O)C1=NN2C(C)=CSC2=C1SSC1=C2SC=C(C)N2N=C1C(=O)OC ZXDBTXLCCSXSBD-UHFFFAOYSA-N 0.000 description 1
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• WQZYOSVPABMXDC-UHFFFAOYSA-N n-tert-butylimidazo[1,5-a]pyridine-1-sulfonamide Chemical compound C1=CC=CC2=C(S(=O)(=O)NC(C)(C)C)N=CN21 WQZYOSVPABMXDC-UHFFFAOYSA-N 0.000 description 1
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• QFBPKODDWQUXSN-UHFFFAOYSA-N o-ethyl 6-benzylimidazo[2,1-b][1,3]thiazole-5-carbothioate Chemical compound N1=C2SC=CN2C(C(=S)OCC)=C1CC1=CC=CC=C1 QFBPKODDWQUXSN-UHFFFAOYSA-N 0.000 description 1
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• QUWUMVASPVYULS-UHFFFAOYSA-N phenyl n-(4-chloro-6-methoxypyrimidin-2-yl)carbamate Chemical compound COC1=CC(Cl)=NC(NC(=O)OC=2C=CC=CC=2)=N1 QUWUMVASPVYULS-UHFFFAOYSA-N 0.000 description 1
• PWNZNGZTYONIEG-UHFFFAOYSA-N phenyl n-(4-methoxy-6-methylpyrimidin-2-yl)carbamate Chemical compound COC1=CC(C)=NC(NC(=O)OC=2C=CC=CC=2)=N1 PWNZNGZTYONIEG-UHFFFAOYSA-N 0.000 description 1
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• LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical compound N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 description 1
• GEYSRRWIBLWTRK-UHFFFAOYSA-N pyrazolo[5,1-b][1,3]thiazole Chemical compound S1C=CN2N=CC=C21 GEYSRRWIBLWTRK-UHFFFAOYSA-N 0.000 description 1
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• CLXNXKPFPIZSKE-UHFFFAOYSA-N pyridazine-3-sulfonamide Chemical compound NS(=O)(=O)C1=CC=CN=N1 CLXNXKPFPIZSKE-UHFFFAOYSA-N 0.000 description 1
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
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• 238000006462 rearrangement reaction Methods 0.000 description 1
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• 230000002940 repellent Effects 0.000 description 1
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• XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 1
• UIDLZBWWANSHHY-UHFFFAOYSA-N s-(5,7-dimethylpyrazolo[1,5-a]pyrimidin-2-yl) n,n-dimethylcarbamothioate Chemical compound N1=C(C)C=C(C)N2N=C(SC(=O)N(C)C)C=C21 UIDLZBWWANSHHY-UHFFFAOYSA-N 0.000 description 1
• 229920006395 saturated elastomer Polymers 0.000 description 1
• 239000000344 soap Substances 0.000 description 1
• URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
• QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
• RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
• 235000010265 sodium sulphite Nutrition 0.000 description 1
• QJDUDPQVDAASMV-UHFFFAOYSA-M sodium;ethanethiolate Chemical compound [Na+].CC[S-] QJDUDPQVDAASMV-UHFFFAOYSA-M 0.000 description 1
• 230000007480 spreading Effects 0.000 description 1
• 238000003892 spreading Methods 0.000 description 1
• 239000003381 stabilizer Substances 0.000 description 1
• 238000006467 substitution reaction Methods 0.000 description 1
• 150000005846 sugar alcohols Polymers 0.000 description 1
• 150000003460 sulfonic acids Chemical class 0.000 description 1
• 239000011593 sulfur Substances 0.000 description 1
• HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
• OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 1
• BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical class O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 description 1
• HFOWWBNMJUVIMH-UHFFFAOYSA-N sulfuryl diisothiocyanate Chemical class S=C=NS(=O)(=O)N=C=S HFOWWBNMJUVIMH-UHFFFAOYSA-N 0.000 description 1
• 239000000725 suspension Substances 0.000 description 1
• 238000003786 synthesis reaction Methods 0.000 description 1
• 239000000454 talc Substances 0.000 description 1
• 229910052623 talc Inorganic materials 0.000 description 1
• 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
• VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
• HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
• HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
• XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
• 125000003944 tolyl group Chemical group 0.000 description 1
• 231100000419 toxicity Toxicity 0.000 description 1
• 230000001988 toxicity Effects 0.000 description 1
• 125000001425 triazolyl group Chemical group 0.000 description 1
• IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
• 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
• 150000003672 ureas Chemical class 0.000 description 1
• 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 235000013311 vegetables Nutrition 0.000 description 1
• 239000004563 wettable powder Substances 0.000 description 1
• 239000000080 wetting agent Substances 0.000 description 1
• 239000002023 wood Substances 0.000 description 1
• 239000011592 zinc chloride Substances 0.000 description 1
• 235000005074 zinc chloride Nutrition 0.000 description 1