JPS6113704B2 - - Google Patents
Info
- Publication number
- JPS6113704B2 JPS6113704B2 JP2302778A JP2302778A JPS6113704B2 JP S6113704 B2 JPS6113704 B2 JP S6113704B2 JP 2302778 A JP2302778 A JP 2302778A JP 2302778 A JP2302778 A JP 2302778A JP S6113704 B2 JPS6113704 B2 JP S6113704B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- atom
- chain
- branched
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 230000002363 herbicidal effect Effects 0.000 claims description 33
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 29
- 239000004009 herbicide Substances 0.000 claims description 27
- 229910052717 sulfur Inorganic materials 0.000 claims description 26
- 125000004434 sulfur atom Chemical group 0.000 claims description 26
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 25
- 125000005843 halogen group Chemical group 0.000 claims description 23
- 125000002947 alkylene group Chemical group 0.000 claims description 22
- SQBHGDSDVWCPHN-UHFFFAOYSA-N 1-methyl-3-phenylurea Chemical class CNC(=O)NC1=CC=CC=C1 SQBHGDSDVWCPHN-UHFFFAOYSA-N 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000004414 alkyl thio group Chemical group 0.000 claims description 13
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 4
- AAVSQBMWOCNSDL-UHFFFAOYSA-N 1-hydroxy-3-phenylurea Chemical class ONC(=O)NC1=CC=CC=C1 AAVSQBMWOCNSDL-UHFFFAOYSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- XGEGHDBEHXKFPX-NJFSPNSNSA-N methylurea Chemical class [14CH3]NC(N)=O XGEGHDBEHXKFPX-NJFSPNSNSA-N 0.000 claims description 3
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical class O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 claims description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
- NNEWRFHYQPTQKR-UHFFFAOYSA-N 1-methoxy-1-methyl-3-phenylurea Chemical class CON(C)C(=O)NC1=CC=CC=C1 NNEWRFHYQPTQKR-UHFFFAOYSA-N 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 claims description 2
- 238000007069 methylation reaction Methods 0.000 claims description 2
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- VMESOKCXSYNAKD-UHFFFAOYSA-N n,n-dimethylhydroxylamine Chemical compound CN(C)O VMESOKCXSYNAKD-UHFFFAOYSA-N 0.000 claims 1
- GRRYSIXDUIAUGY-UHFFFAOYSA-N n-methylcarbamoyl chloride Chemical compound CNC(Cl)=O GRRYSIXDUIAUGY-UHFFFAOYSA-N 0.000 claims 1
- -1 propylthio group Chemical group 0.000 description 59
- 150000001875 compounds Chemical class 0.000 description 47
- 241000196324 Embryophyta Species 0.000 description 37
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000000126 substance Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 235000019441 ethanol Nutrition 0.000 description 10
- 239000002689 soil Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 8
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- 240000007594 Oryza sativa Species 0.000 description 7
- 235000007164 Oryza sativa Nutrition 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- 235000005733 Raphanus sativus var niger Nutrition 0.000 description 7
- 240000001970 Raphanus sativus var. sativus Species 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 235000009566 rice Nutrition 0.000 description 7
- 244000068988 Glycine max Species 0.000 description 6
- 235000010469 Glycine max Nutrition 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 241000209140 Triticum Species 0.000 description 6
- 235000021307 Triticum Nutrition 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 5
- 244000058871 Echinochloa crus-galli Species 0.000 description 5
- 231100000674 Phytotoxicity Toxicity 0.000 description 5
- 235000021536 Sugar beet Nutrition 0.000 description 5
- 240000008042 Zea mays Species 0.000 description 5
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 5
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 5
- 235000005822 corn Nutrition 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 231100000053 low toxicity Toxicity 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 230000029553 photosynthesis Effects 0.000 description 5
- 238000010672 photosynthesis Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 241000219146 Gossypium Species 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 150000001448 anilines Chemical class 0.000 description 4
- 239000004927 clay Substances 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 230000007480 spreading Effects 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 244000025254 Cannabis sativa Species 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
- 240000003173 Drymaria cordata Species 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 235000013312 flour Nutrition 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- CTSLUCNDVMMDHG-UHFFFAOYSA-N 5-bromo-3-(butan-2-yl)-6-methylpyrimidine-2,4(1H,3H)-dione Chemical compound CCC(C)N1C(=O)NC(C)=C(Br)C1=O CTSLUCNDVMMDHG-UHFFFAOYSA-N 0.000 description 2
- 241000254032 Acrididae Species 0.000 description 2
- 240000001592 Amaranthus caudatus Species 0.000 description 2
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 244000301850 Cupressus sempervirens Species 0.000 description 2
- 239000005510 Diuron Substances 0.000 description 2
- 244000020551 Helianthus annuus Species 0.000 description 2
- 235000003222 Helianthus annuus Nutrition 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 240000001549 Ipomoea eriocarpa Species 0.000 description 2
- 235000005146 Ipomoea eriocarpa Nutrition 0.000 description 2
- 229920001732 Lignosulfonate Polymers 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- 244000234609 Portulaca oleracea Species 0.000 description 2
- 235000001855 Portulaca oleracea Nutrition 0.000 description 2
- 241000208422 Rhododendron Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
- 229920002472 Starch Polymers 0.000 description 2
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
- 244000078534 Vaccinium myrtillus Species 0.000 description 2
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 2
- 239000003048 aphrodisiac agent Substances 0.000 description 2
- 230000002509 aphrodisiac effect Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 230000000887 hydrating effect Effects 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 244000144972 livestock Species 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 1
- IXJJELULBDAIMY-UHFFFAOYSA-N 1,2,5,6-tetrahydrotriazine Chemical compound C1CC=NNN1 IXJJELULBDAIMY-UHFFFAOYSA-N 0.000 description 1
- OWNQIBZZHGAEDS-UHFFFAOYSA-N 1,2-dichloro-4-[3-(3-isocyanatophenoxy)propyl]benzene Chemical compound C1=C(Cl)C(Cl)=CC=C1CCCOC1=CC=CC(N=C=O)=C1 OWNQIBZZHGAEDS-UHFFFAOYSA-N 0.000 description 1
- 125000004815 1,2-dimethylethylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([*:2])C([H])([H])[H] 0.000 description 1
- XXRBJMPVYKNDPG-UHFFFAOYSA-N 1-(3-bromopropyl)-4-methylbenzene Chemical compound CC1=CC=C(CCCBr)C=C1 XXRBJMPVYKNDPG-UHFFFAOYSA-N 0.000 description 1
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- IGXOYZTVJZZSNS-UHFFFAOYSA-N 1-isocyanato-3-(3-phenylpropoxy)benzene Chemical compound O=C=NC1=CC=CC(OCCCC=2C=CC=CC=2)=C1 IGXOYZTVJZZSNS-UHFFFAOYSA-N 0.000 description 1
- OBGFMRSXJROQDT-UHFFFAOYSA-N 1-methoxy-1-methylurea Chemical compound CON(C)C(N)=O OBGFMRSXJROQDT-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- 125000004806 1-methylethylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000004816 2,2-dimethylethylene group Chemical group [H]C([H])([H])C([*:2])(C([H])([H])[H])C([H])([H])[*:1] 0.000 description 1
- YIVXMZJTEQBPQO-UHFFFAOYSA-N 2,4-DB Chemical compound OC(=O)CCCOC1=CC=C(Cl)C=C1Cl YIVXMZJTEQBPQO-UHFFFAOYSA-N 0.000 description 1
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 1
- HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-N 0.000 description 1
- QXXIZJPWGJDHKR-UHFFFAOYSA-N 2,6-dinitro-n-propyl-4-(trifluoromethyl)aniline Chemical compound CCCNC1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O QXXIZJPWGJDHKR-UHFFFAOYSA-N 0.000 description 1
- OWZPCEFYPSAJFR-UHFFFAOYSA-N 2-(butan-2-yl)-4,6-dinitrophenol Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O OWZPCEFYPSAJFR-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- HXDLWJWIAHWIKI-UHFFFAOYSA-N 2-hydroxyethyl acetate Chemical compound CC(=O)OCCO HXDLWJWIAHWIKI-UHFFFAOYSA-N 0.000 description 1
- 125000004807 2-methylethylene group Chemical group [H]C([H])([H])C([H])([*:2])C([H])([H])[*:1] 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- TVHCLUNXRJSPGX-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-1,1-dimethylurea;3-(3,4-dichlorophenyl)-1-methoxy-1-methylurea Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1.CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 TVHCLUNXRJSPGX-UHFFFAOYSA-N 0.000 description 1
- BKRFNKBPFZWDPA-UHFFFAOYSA-N 3-(4-phenylbutoxy)aniline Chemical compound NC1=CC=CC(OCCCCC=2C=CC=CC=2)=C1 BKRFNKBPFZWDPA-UHFFFAOYSA-N 0.000 description 1
- ILOZECIQNMSVCK-UHFFFAOYSA-N 4-methyl-n,n-dipropylaniline Chemical compound CCCN(CCC)C1=CC=C(C)C=C1 ILOZECIQNMSVCK-UHFFFAOYSA-N 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- MYRZHMIBRIKWDO-UHFFFAOYSA-N 4h-triazin-5-one Chemical compound O=C1CN=NN=C1 MYRZHMIBRIKWDO-UHFFFAOYSA-N 0.000 description 1
- MDOQZDIZLVBOMT-UHFFFAOYSA-N 5-bromo-3-butan-2-yl-1h-pyrimidine-2,4-dione Chemical compound CCC(C)N1C(=O)NC=C(Br)C1=O MDOQZDIZLVBOMT-UHFFFAOYSA-N 0.000 description 1
- DFGKGUXTPFWHIX-UHFFFAOYSA-N 6-[2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]acetyl]-3H-1,3-benzoxazol-2-one Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)C1=CC2=C(NC(O2)=O)C=C1 DFGKGUXTPFWHIX-UHFFFAOYSA-N 0.000 description 1
- NMKIWDGUSGQUQO-UHFFFAOYSA-N 6-tert-butyl-3-methylsulfanyl-3h-1,2,4-triazin-4-amine Chemical compound CSC1N=NC(C(C)(C)C)=CN1N NMKIWDGUSGQUQO-UHFFFAOYSA-N 0.000 description 1
- 241001311476 Abies veitchii Species 0.000 description 1
- 244000045410 Aegopodium podagraria Species 0.000 description 1
- 235000007237 Aegopodium podagraria Nutrition 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000208841 Ambrosia trifida Species 0.000 description 1
- 241000208173 Apiaceae Species 0.000 description 1
- 241000209763 Avena sativa Species 0.000 description 1
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Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (24)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2302778A JPS54115347A (en) | 1978-02-28 | 1978-02-28 | Substituted-phenylurea deriavtive, its preparation and herbicide containing the same |
| US05/952,775 US4309212A (en) | 1977-10-26 | 1978-10-19 | Herbicidal compositions and methods employing urea derivatives |
| MX787486U MX5191E (es) | 1977-10-26 | 1978-10-25 | Procedimiento para la preparacion de derivados de n'-fenil-n-metilurea |
| CH1101278A CH641770A5 (de) | 1977-10-26 | 1978-10-25 | Harnstoffderivate. |
| AU41058/78A AU522936B2 (en) | 1977-10-26 | 1978-10-25 | Urea derivatives |
| GB7841843A GB2010244B (en) | 1977-10-26 | 1978-10-25 | Urea derivatives |
| HU78SU994A HU177145B (en) | 1977-10-26 | 1978-10-25 | Herbicide and fungicide compositions containing n'-pheny |
| BG7841191A BG33731A3 (en) | 1977-10-26 | 1978-10-25 | Herbicide means and method for neuralization of weeds |
| FR7830348A FR2407201A1 (fr) | 1977-10-26 | 1978-10-25 | Procede de production de n'-phenyl-n-methyluree, nouveaux produits ainsi obtenus et leur utilisation comme agents fongicides |
| PL1978210522A PL118309B1 (en) | 1977-10-26 | 1978-10-26 | Herbicide |
| CA314,319A CA1108184A (en) | 1977-10-26 | 1978-10-26 | Urea derivatives, and their production and use |
| DD78208696A DD139711A5 (de) | 1977-10-26 | 1978-10-26 | Verfahren zur herstellung von n'-phenyl-n-methylharnstoff-derivaten |
| NL7810700A NL7810700A (nl) | 1977-10-26 | 1978-10-26 | Ureumderivaten, de bereidingswijze en toepassing daarvan. |
| IT69470/78A IT1160892B (it) | 1977-10-26 | 1978-10-26 | Derivati dell'urea particolarmente utili come erbicidi e fungicidi e procedimento per la loro preparazione |
| DK478078A DK478078A (da) | 1977-10-26 | 1978-10-26 | Urinstofderivater deres fremstilling og anvendelse |
| YU02504/78A YU250478A (en) | 1977-10-26 | 1978-10-26 | Process for obtaining new n'phenyl-n-methylcarbamide derivatives |
| BR7807054A BR7807054A (pt) | 1977-10-26 | 1978-10-26 | Composto,processo para sua preparacao,composicao herbicida processo para controle de ervas daninhas,processo para combate seletivo das ultimas,composicao fungicidas,e processo para controle de fungos |
| AR274239A AR229391A1 (es) | 1977-10-26 | 1978-10-26 | Derivados de n'-fenil-n-metilurea,el procedimiento para obtenerlos y composiciones herbicidas o fungicidas que contienen a dichos derivados como agente activo |
| ES474581A ES474581A1 (es) | 1977-10-26 | 1978-10-26 | Un procedimiento para la preparacion de nuevos derivados de n'-fenil-n-metilurea |
| CS786968A CS201516B2 (en) | 1977-10-26 | 1978-10-26 | Herbicide or fungicide means |
| DE19782846723 DE2846723A1 (de) | 1977-10-26 | 1978-10-26 | N'-phenyl-n-methylharnstoff-derivate |
| ES480717A ES480717A1 (es) | 1977-10-26 | 1979-05-18 | Un procedimiento para la preparacion de nuevos derivados de n-fenil-n-metilurea. |
| ES480718A ES480718A1 (es) | 1977-10-26 | 1979-05-18 | Un procedimiento para la preparacion de nuevos derivados de anilina. |
| US06/203,485 US4690709A (en) | 1977-10-26 | 1980-11-03 | Urea derivatives, and their use as herbicides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2302778A JPS54115347A (en) | 1978-02-28 | 1978-02-28 | Substituted-phenylurea deriavtive, its preparation and herbicide containing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS54115347A JPS54115347A (en) | 1979-09-07 |
| JPS6113704B2 true JPS6113704B2 (US08063081-20111122-C00044.png) | 1986-04-15 |
Family
ID=12098982
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2302778A Granted JPS54115347A (en) | 1977-10-26 | 1978-02-28 | Substituted-phenylurea deriavtive, its preparation and herbicide containing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS54115347A (US08063081-20111122-C00044.png) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63117808U (US08063081-20111122-C00044.png) * | 1987-01-20 | 1988-07-29 | ||
| JPH01118009U (US08063081-20111122-C00044.png) * | 1988-01-29 | 1989-08-09 |
-
1978
- 1978-02-28 JP JP2302778A patent/JPS54115347A/ja active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63117808U (US08063081-20111122-C00044.png) * | 1987-01-20 | 1988-07-29 | ||
| JPH01118009U (US08063081-20111122-C00044.png) * | 1988-01-29 | 1989-08-09 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS54115347A (en) | 1979-09-07 |
