DD202374A5 - Herbizide mittel - Google Patents
Herbizide mittel Download PDFInfo
- Publication number
- DD202374A5 DD202374A5 DD82237349A DD23734982A DD202374A5 DD 202374 A5 DD202374 A5 DD 202374A5 DD 82237349 A DD82237349 A DD 82237349A DD 23734982 A DD23734982 A DD 23734982A DD 202374 A5 DD202374 A5 DD 202374A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- group
- isocyanate
- propane
- chloropropyl
- compounds
- Prior art date
Links
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 21
- 239000004009 herbicide Substances 0.000 title claims abstract description 12
- 241000196324 Embryophyta Species 0.000 claims abstract description 36
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 33
- 238000002360 preparation method Methods 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 16
- 230000008569 process Effects 0.000 claims description 14
- 239000004094 surface-active agent Substances 0.000 claims description 6
- NQPJDJVGBDHCAD-UHFFFAOYSA-N 1,3-diazinan-2-one Chemical class OC1=NCCCN1 NQPJDJVGBDHCAD-UHFFFAOYSA-N 0.000 claims description 5
- 239000004606 Fillers/Extenders Substances 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- -1 alpha-naphthyl group Chemical group 0.000 abstract description 27
- 239000003795 chemical substances by application Substances 0.000 abstract description 7
- 239000004480 active ingredient Substances 0.000 abstract description 3
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- 229910052736 halogen Inorganic materials 0.000 abstract description 2
- 150000002367 halogens Chemical class 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 description 62
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 9
- 239000008187 granular material Substances 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 240000007594 Oryza sativa Species 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000853 adhesive Substances 0.000 description 6
- 230000001070 adhesive effect Effects 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 235000007164 Oryza sativa Nutrition 0.000 description 5
- 231100000674 Phytotoxicity Toxicity 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 235000009566 rice Nutrition 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 244000058871 Echinochloa crus-galli Species 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 235000011999 Panicum crusgalli Nutrition 0.000 description 4
- 239000004372 Polyvinyl alcohol Substances 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 239000003905 agrochemical Substances 0.000 description 4
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000004927 clay Substances 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 229920002451 polyvinyl alcohol Polymers 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 231100000419 toxicity Toxicity 0.000 description 4
- 230000001988 toxicity Effects 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- SMPFVGOGVVEABT-XWHIBYANSA-N 3-[[(4r,5r,6r)-4-benzyl-5-hydroxy-3-[[3-[(z)-n'-hydroxycarbamimidoyl]phenyl]methyl]-2-oxo-6-(2-phenylethyl)-1,3-diazinan-1-yl]methyl]-n'-hydroxybenzenecarboximidamide Chemical class O\N=C(/N)C1=CC=CC(CN2C(N(CC=3C=C(C=CC=3)C(\N)=N\O)[C@H](CC=3C=CC=CC=3)[C@H](O)[C@H]2CCC=2C=CC=CC=2)=O)=C1 SMPFVGOGVVEABT-XWHIBYANSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 244000285790 Cyperus iria Species 0.000 description 3
- 241000759199 Eleocharis acicularis Species 0.000 description 3
- 241000209510 Liliopsida Species 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 240000000178 Monochoria vaginalis Species 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 241001408202 Sagittaria pygmaea Species 0.000 description 3
- 244000085269 Scirpus juncoides Species 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 230000002140 halogenating effect Effects 0.000 description 3
- 239000003701 inert diluent Substances 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 244000082735 tidal marsh flat sedge Species 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- XEFUJGURFLOFAN-UHFFFAOYSA-N 1,3-dichloro-5-isocyanatobenzene Chemical compound ClC1=CC(Cl)=CC(N=C=O)=C1 XEFUJGURFLOFAN-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- SUVCZZADQDCIEQ-UHFFFAOYSA-N 1-isocyanato-2-methoxybenzene Chemical compound COC1=CC=CC=C1N=C=O SUVCZZADQDCIEQ-UHFFFAOYSA-N 0.000 description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- GZYBSURBYCLNSM-UHFFFAOYSA-N 3-anilinopropan-1-ol Chemical compound OCCCNC1=CC=CC=C1 GZYBSURBYCLNSM-UHFFFAOYSA-N 0.000 description 2
- 244000056139 Brassica cretica Species 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 244000283628 Elatine triandra Species 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 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 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 244000155504 Rotala indica Species 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
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- 238000010790 dilution Methods 0.000 description 2
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- 229940113088 dimethylacetamide Drugs 0.000 description 2
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
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- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- RHDOKCOTTDTSJA-UHFFFAOYSA-N n-(3-chloropropyl)-3-(trifluoromethyl)aniline Chemical compound FC(F)(F)C1=CC=CC(NCCCCl)=C1 RHDOKCOTTDTSJA-UHFFFAOYSA-N 0.000 description 2
- IVIHOASIIBQWPU-UHFFFAOYSA-N n-phenyl-n'-[3-(trifluoromethyl)phenyl]propane-1,3-diamine Chemical compound FC(F)(F)C1=CC=CC(NCCCNC=2C=CC=CC=2)=C1 IVIHOASIIBQWPU-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
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- 125000001424 substituent group Chemical group 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
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- 229910052623 talc Inorganic materials 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 1
- RDUIJJYNVCVETK-UHFFFAOYSA-N 1,2,4-trichloro-5-isocyanatobenzene Chemical compound ClC1=CC(Cl)=C(N=C=O)C=C1Cl RDUIJJYNVCVETK-UHFFFAOYSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- PEQMJVGRHNZPAM-UHFFFAOYSA-N 1,4-dichloro-2-isocyanatobenzene Chemical compound ClC1=CC=C(Cl)C(N=C=O)=C1 PEQMJVGRHNZPAM-UHFFFAOYSA-N 0.000 description 1
- XZDGRFYWAXMRKD-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)-3-phenyl-1,3-diazinan-2-one Chemical compound ClC1=CC(Cl)=CC(N2C(N(CCC2)C=2C=CC=CC=2)=O)=C1 XZDGRFYWAXMRKD-UHFFFAOYSA-N 0.000 description 1
- JASTZOAHAWBRLM-UHFFFAOYSA-N 1-(3-isocyanatophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(N=C=O)=C1 JASTZOAHAWBRLM-UHFFFAOYSA-N 0.000 description 1
- SPVZFPMAGSKRCE-UHFFFAOYSA-N 1-[3-(3-anilinopropylamino)phenyl]ethanone Chemical compound CC(=O)C1=CC=CC(NCCCNC=2C=CC=CC=2)=C1 SPVZFPMAGSKRCE-UHFFFAOYSA-N 0.000 description 1
- RMECPWUFFIWWBC-UHFFFAOYSA-N 1-[3-(3-chloropropylamino)phenyl]ethanone Chemical compound CC(=O)C1=CC=CC(NCCCCl)=C1 RMECPWUFFIWWBC-UHFFFAOYSA-N 0.000 description 1
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- HHIRBXHEYVDUAM-UHFFFAOYSA-N 1-chloro-3-isocyanatobenzene Chemical compound ClC1=CC=CC(N=C=O)=C1 HHIRBXHEYVDUAM-UHFFFAOYSA-N 0.000 description 1
- ADAKRBAJFHTIEW-UHFFFAOYSA-N 1-chloro-4-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1 ADAKRBAJFHTIEW-UHFFFAOYSA-N 0.000 description 1
- RIKWVZGZRYDACA-UHFFFAOYSA-N 1-fluoro-3-isocyanatobenzene Chemical compound FC1=CC=CC(N=C=O)=C1 RIKWVZGZRYDACA-UHFFFAOYSA-N 0.000 description 1
- GZWGTVZRRFPVAS-UHFFFAOYSA-N 1-isocyanato-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1N=C=O GZWGTVZRRFPVAS-UHFFFAOYSA-N 0.000 description 1
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- DZSGDHNHQAJZCO-UHFFFAOYSA-N 1-isocyanato-3,5-dimethylbenzene Chemical compound CC1=CC(C)=CC(N=C=O)=C1 DZSGDHNHQAJZCO-UHFFFAOYSA-N 0.000 description 1
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- CPPGZWWUPFWALU-UHFFFAOYSA-N 1-isocyanato-3-methylbenzene Chemical compound CC1=CC=CC(N=C=O)=C1 CPPGZWWUPFWALU-UHFFFAOYSA-N 0.000 description 1
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- PJVRNNRZWASOIT-UHFFFAOYSA-N 1-isocyanato-4-propan-2-ylbenzene Chemical compound CC(C)C1=CC=C(N=C=O)C=C1 PJVRNNRZWASOIT-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
- DEGUTTXNZWYLKV-UHFFFAOYSA-N 1-methyl-3-phenyl-1,3-diazinan-2-one Chemical compound O=C1N(C)CCCN1C1=CC=CC=C1 DEGUTTXNZWYLKV-UHFFFAOYSA-N 0.000 description 1
- VFMOVKIZQPSTJS-UHFFFAOYSA-N 2,4,5-trichloro-n-(3-chloropropyl)aniline Chemical compound ClCCCNC1=CC(Cl)=C(Cl)C=C1Cl VFMOVKIZQPSTJS-UHFFFAOYSA-N 0.000 description 1
- AWWVBIIJHFTNKW-UHFFFAOYSA-N 2,5-dichloro-n-(3-chloropropyl)aniline Chemical compound ClCCCNC1=CC(Cl)=CC=C1Cl AWWVBIIJHFTNKW-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- HCWZJEXQULSHSD-UHFFFAOYSA-N 2-chloro-4-isocyanato-1-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(N=C=O)C=C1Cl HCWZJEXQULSHSD-UHFFFAOYSA-N 0.000 description 1
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- 239000003380 propellant Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms directly attached in position 2
- C07D239/10—Oxygen or sulfur atoms
-
- 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
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56023122A JPS57139069A (en) | 1981-02-20 | 1981-02-20 | Substituted tetrahydropyrimidinone derivative, its preparation and herbicide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD202374A5 true DD202374A5 (de) | 1983-09-14 |
Family
ID=12101692
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD82237349A DD202374A5 (de) | 1981-02-20 | 1982-02-11 | Herbizide mittel |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4402731A (pt) |
| EP (1) | EP0058868B1 (pt) |
| JP (1) | JPS57139069A (pt) |
| KR (1) | KR830009051A (pt) |
| AR (1) | AR228768A1 (pt) |
| AT (1) | ATE7027T1 (pt) |
| AU (1) | AU548087B2 (pt) |
| BR (1) | BR8200916A (pt) |
| CA (1) | CA1166250A (pt) |
| CS (1) | CS231991B2 (pt) |
| DD (1) | DD202374A5 (pt) |
| DE (1) | DE3260098D1 (pt) |
| DK (1) | DK74182A (pt) |
| ES (1) | ES8307003A1 (pt) |
| GR (1) | GR75868B (pt) |
| HU (1) | HU187447B (pt) |
| IL (1) | IL65039A (pt) |
| PH (1) | PH17047A (pt) |
| PL (1) | PL235150A1 (pt) |
| PT (1) | PT74412B (pt) |
| TR (1) | TR20938A (pt) |
| ZA (1) | ZA821101B (pt) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2975456A (en) * | 1956-08-03 | 1961-03-21 | Gen Electric | Vacuum cleaning nozzle attachment for high pile rugs |
| JPS58140078A (ja) * | 1982-02-16 | 1983-08-19 | Nippon Tokushu Noyaku Seizo Kk | メチル置換テトラヒドロ−２−ピリミジノン誘導体、その製法、その中間体及び該中間体の製法、並びに除草剤 |
| DE3709574A1 (de) * | 1987-03-24 | 1988-10-06 | Bayer Ag | Substituierte triazolinone |
| DE19962923A1 (de) | 1999-12-24 | 2001-07-05 | Bayer Ag | Substituierte Benzoylcyclohexandione |
| CA2493458A1 (en) * | 2002-07-24 | 2004-01-29 | Ptc Therapeutics, Inc. | Ureido substituted benzoic acid compounds, their use for nonsense suppression and the treatment of diseases caused by such mutations |
| US9181261B2 (en) | 2012-05-22 | 2015-11-10 | Merck Sharp & Dohme Corp. | TrkA kinase inhibitors, compositions and methods thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3551425A (en) * | 1967-07-01 | 1970-12-29 | Basf Ag | Production of 2-oxohexahydropyrimidines |
| FR2194369B1 (pt) * | 1972-08-04 | 1980-04-25 | Roussel Uclaf | |
| IT1026907B (it) * | 1974-12-10 | 1978-10-20 | Snam Progetti | Procedimento per la sintesi di uree |
-
1981
- 1981-02-20 JP JP56023122A patent/JPS57139069A/ja active Pending
-
1982
- 1982-01-20 US US06/340,949 patent/US4402731A/en not_active Expired - Fee Related
- 1982-02-03 PH PH26823A patent/PH17047A/en unknown
- 1982-02-04 AU AU80184/82A patent/AU548087B2/en not_active Expired - Fee Related
- 1982-02-09 DE DE8282100905T patent/DE3260098D1/de not_active Expired
- 1982-02-09 EP EP82100905A patent/EP0058868B1/de not_active Expired
- 1982-02-09 AT AT82100905T patent/ATE7027T1/de not_active IP Right Cessation
- 1982-02-10 PT PT74412A patent/PT74412B/pt unknown
- 1982-02-11 DD DD82237349A patent/DD202374A5/de unknown
- 1982-02-17 IL IL65039A patent/IL65039A/xx unknown
- 1982-02-18 GR GR67347A patent/GR75868B/el unknown
- 1982-02-18 TR TR20938A patent/TR20938A/xx unknown
- 1982-02-19 CS CS821170A patent/CS231991B2/cs unknown
- 1982-02-19 AR AR288482A patent/AR228768A1/es active
- 1982-02-19 BR BR8200916A patent/BR8200916A/pt unknown
- 1982-02-19 DK DK74182A patent/DK74182A/da unknown
- 1982-02-19 PL PL23515082A patent/PL235150A1/xx unknown
- 1982-02-19 HU HU82513A patent/HU187447B/hu unknown
- 1982-02-19 ES ES509744A patent/ES8307003A1/es not_active Expired
- 1982-02-19 CA CA000396634A patent/CA1166250A/en not_active Expired
- 1982-02-19 ZA ZA821101A patent/ZA821101B/xx unknown
- 1982-02-20 KR KR1019820000751A patent/KR830009051A/ko unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US4402731A (en) | 1983-09-06 |
| IL65039A (en) | 1984-12-31 |
| EP0058868B1 (de) | 1984-04-11 |
| EP0058868A1 (de) | 1982-09-01 |
| HU187447B (en) | 1986-01-28 |
| GR75868B (pt) | 1984-08-02 |
| IL65039A0 (en) | 1982-04-30 |
| TR20938A (tr) | 1983-01-20 |
| BR8200916A (pt) | 1982-12-28 |
| JPS57139069A (en) | 1982-08-27 |
| AU548087B2 (en) | 1985-11-21 |
| ATE7027T1 (de) | 1984-04-15 |
| CA1166250A (en) | 1984-04-24 |
| PH17047A (en) | 1984-05-17 |
| DK74182A (da) | 1982-08-21 |
| CS117082A2 (en) | 1984-01-16 |
| KR830009051A (ko) | 1983-12-17 |
| DE3260098D1 (en) | 1984-05-17 |
| ES509744A0 (es) | 1983-06-16 |
| ES8307003A1 (es) | 1983-06-16 |
| ZA821101B (en) | 1983-01-26 |
| PT74412A (en) | 1982-03-01 |
| PT74412B (en) | 1983-07-08 |
| PL235150A1 (en) | 1983-04-11 |
| AR228768A1 (es) | 1983-04-15 |
| CS231991B2 (en) | 1985-01-16 |
| AU8018482A (en) | 1982-08-26 |
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