JPS625432B2 - - Google Patents

Info

Publication number

JPS625432B2

JPS625432B2 JP9159383A JP9159383A JPS625432B2 JP S625432 B2 JPS625432 B2 JP S625432B2 JP 9159383 A JP9159383 A JP 9159383A JP 9159383 A JP9159383 A JP 9159383A JP S625432 B2 JPS625432 B2 JP S625432B2

Authority

JP

Japan

Prior art keywords

formula

atom

group

general formula

benzene

Prior art date

1983-05-26

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

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• 230000002363 herbicidal effect Effects 0.000 claims description 9
• 125000005843 halogen group Chemical group 0.000 claims description 7
• 125000000217 alkyl group Chemical group 0.000 claims description 6
• 239000004009 herbicide Substances 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• AKZWRTCWNXHHFR-PDIZUQLASA-N [(3S)-oxolan-3-yl] N-[(2S,3S)-4-[(5S)-5-benzyl-3-[(2R)-2-carbamoyloxy-2,3-dihydro-1H-inden-1-yl]-4-oxo-3H-pyrrol-5-yl]-3-hydroxy-1-phenylbutan-2-yl]carbamate Chemical compound NC(=O)O[C@@H]1Cc2ccccc2C1C1C=N[C@](C[C@H](O)[C@H](Cc2ccccc2)NC(=O)O[C@H]2CCOC2)(Cc2ccccc2)C1=O AKZWRTCWNXHHFR-PDIZUQLASA-N 0.000 claims description 5
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
• 229910052717 sulfur Inorganic materials 0.000 claims description 5
• 125000004434 sulfur atom Chemical group 0.000 claims description 5
• 239000004480 active ingredient Substances 0.000 claims description 4
• 125000004997 halocarbonyl group Chemical group 0.000 claims 3
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
• 150000003927 aminopyridines Chemical class 0.000 claims 1
• 150000004657 carbamic acid derivatives Chemical class 0.000 claims 1
• 150000004780 naphthols Chemical class 0.000 claims 1
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 40
• 150000001875 compounds Chemical class 0.000 description 12
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
• 241000196324 Embryophyta Species 0.000 description 8
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• 238000006243 chemical reaction Methods 0.000 description 6
• 238000003359 percent control normalization Methods 0.000 description 6
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
• 239000000243 solution Substances 0.000 description 6
• 241000209094 Oryza Species 0.000 description 5
• 235000007164 Oryza sativa Nutrition 0.000 description 5
• -1 calcium hydroxide Chemical class 0.000 description 5
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
• 235000009566 rice Nutrition 0.000 description 5
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
• 239000003795 chemical substances by application Substances 0.000 description 4
• 238000002844 melting Methods 0.000 description 4
• 230000008018 melting Effects 0.000 description 4
• 238000003756 stirring Methods 0.000 description 4
• 244000025254 Cannabis sativa Species 0.000 description 3
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
• 238000004440 column chromatography Methods 0.000 description 3
• 230000006378 damage Effects 0.000 description 3
• 229910000027 potassium carbonate Inorganic materials 0.000 description 3
• 235000011181 potassium carbonates Nutrition 0.000 description 3
• 239000011541 reaction mixture Substances 0.000 description 3
• 238000010992 reflux Methods 0.000 description 3
• 239000000741 silica gel Substances 0.000 description 3
• 229910002027 silica gel Inorganic materials 0.000 description 3
• JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 2
• QTKZLRUCDNUBGM-UHFFFAOYSA-N 2h-pyridin-1-yl carbamate Chemical class NC(=O)ON1CC=CC=C1 QTKZLRUCDNUBGM-UHFFFAOYSA-N 0.000 description 2
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
• YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
• 239000007810 chemical reaction solvent Substances 0.000 description 2
• 239000013078 crystal Substances 0.000 description 2
• 230000000694 effects Effects 0.000 description 2
• 238000000921 elemental analysis Methods 0.000 description 2
• GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 2
• 239000002994 raw material Substances 0.000 description 2
• 229920006395 saturated elastomer Polymers 0.000 description 2
• 239000011780 sodium chloride Substances 0.000 description 2
• 239000002689 soil Substances 0.000 description 2
• 239000007787 solid Substances 0.000 description 2
• 239000000126 substance Substances 0.000 description 2
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
• RYSVVUSXJOEDJY-UHFFFAOYSA-N (6-methylpyridin-2-yl) N-methylcarbamate Chemical compound CNC(=O)OC1=NC(=CC=C1)C RYSVVUSXJOEDJY-UHFFFAOYSA-N 0.000 description 1
• SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
• MAKFMOSBBNKPMS-UHFFFAOYSA-N 2,3-dichloropyridine Chemical compound ClC1=CC=CN=C1Cl MAKFMOSBBNKPMS-UHFFFAOYSA-N 0.000 description 1
• VPGPNOQDNGMIKA-UHFFFAOYSA-N 6-chloro-n-methylpyridin-2-amine Chemical compound CNC1=CC=CC(Cl)=N1 VPGPNOQDNGMIKA-UHFFFAOYSA-N 0.000 description 1
• LLLALLARMSBOTR-UHFFFAOYSA-N CNC1=CC=C(C)C(C)=N1 Chemical compound CNC1=CC=C(C)C(C)=N1 LLLALLARMSBOTR-UHFFFAOYSA-N 0.000 description 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
• JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
• 150000001298 alcohols Chemical class 0.000 description 1
• 239000003513 alkali Substances 0.000 description 1
• 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
• 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
• 230000000844 anti-bacterial effect Effects 0.000 description 1
• 239000007864 aqueous solution Substances 0.000 description 1
• 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
• 125000003118 aryl group Chemical group 0.000 description 1
• 229950011260 betanaphthol Drugs 0.000 description 1
• AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
• 239000000920 calcium hydroxide Substances 0.000 description 1
• 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
• 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
• 239000000460 chlorine Substances 0.000 description 1
• 229910052801 chlorine Inorganic materials 0.000 description 1
• 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
• HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 1
• 229940079593 drug Drugs 0.000 description 1
• 239000003814 drug Substances 0.000 description 1
• 150000002170 ethers Chemical class 0.000 description 1
• 238000011156 evaluation Methods 0.000 description 1
• 238000001914 filtration Methods 0.000 description 1
• 150000008282 halocarbons Chemical class 0.000 description 1
• 230000000887 hydrating effect Effects 0.000 description 1
• 150000004679 hydroxides Chemical class 0.000 description 1
• 150000002576 ketones Chemical class 0.000 description 1
• 229910052987 metal hydride Inorganic materials 0.000 description 1
• 150000004681 metal hydrides Chemical class 0.000 description 1
• 238000000034 method Methods 0.000 description 1
• 239000000203 mixture Substances 0.000 description 1
• 230000009526 moderate injury Effects 0.000 description 1
• FDKUOSVCAQGJIN-UHFFFAOYSA-N n-methyl-n-(6-methylpyridin-2-yl)carbamoyl chloride Chemical compound ClC(=O)N(C)C1=CC=CC(C)=N1 FDKUOSVCAQGJIN-UHFFFAOYSA-N 0.000 description 1
• SVEUVITYHIHZQE-UHFFFAOYSA-N n-methylpyridin-2-amine Chemical compound CNC1=CC=CC=N1 SVEUVITYHIHZQE-UHFFFAOYSA-N 0.000 description 1
• 239000002798 polar solvent Substances 0.000 description 1
• 229910052573 porcelain Inorganic materials 0.000 description 1
• 239000011736 potassium bicarbonate Substances 0.000 description 1
• 235000015497 potassium bicarbonate Nutrition 0.000 description 1
• 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
• TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
• 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
• 150000003222 pyridines Chemical class 0.000 description 1
• 230000035484 reaction time Effects 0.000 description 1
• 230000009528 severe injury Effects 0.000 description 1
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
• 235000017557 sodium bicarbonate Nutrition 0.000 description 1
• 229910000029 sodium carbonate Inorganic materials 0.000 description 1
• 235000017550 sodium carbonate Nutrition 0.000 description 1
• 239000002344 surface layer Substances 0.000 description 1
• 150000003512 tertiary amines Chemical class 0.000 description 1
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
• 238000009333 weeding Methods 0.000 description 1
• 239000008096 xylene Substances 0.000 description 1

Cited By (2)