CA1135703A - 4,5-dichloroimidazole derivatives, processes for their preparation and their use as herbicides - Google Patents
4,5-dichloroimidazole derivatives, processes for their preparation and their use as herbicidesInfo
- Publication number
- CA1135703A CA1135703A CA000343849A CA343849A CA1135703A CA 1135703 A CA1135703 A CA 1135703A CA 000343849 A CA000343849 A CA 000343849A CA 343849 A CA343849 A CA 343849A CA 1135703 A CA1135703 A CA 1135703A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- hydrogen
- chlorine
- imidazole
- dichloro
- 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
- 238000000034 method Methods 0.000 title claims description 135
- QAJJXHRQPLATMK-UHFFFAOYSA-N 4,5-dichloro-1h-imidazole Chemical class ClC=1N=CNC=1Cl QAJJXHRQPLATMK-UHFFFAOYSA-N 0.000 title claims description 30
- 239000004009 herbicide Substances 0.000 title abstract description 8
- 238000002360 preparation method Methods 0.000 title description 17
- 239000000460 chlorine Chemical group 0.000 claims abstract description 131
- 150000001875 compounds Chemical class 0.000 claims abstract description 105
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 54
- 239000001257 hydrogen Substances 0.000 claims abstract description 48
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 48
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 44
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 31
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 31
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 31
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 11
- 239000001301 oxygen Substances 0.000 claims abstract description 11
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000011630 iodine Chemical group 0.000 claims abstract description 10
- 229910052740 iodine Chemical group 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- 125000001424 substituent group Chemical group 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 150000002367 halogens Chemical class 0.000 claims abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 4
- 239000011593 sulfur Substances 0.000 claims abstract 4
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract 2
- 241000196324 Embryophyta Species 0.000 claims description 25
- -1 4,5-Dichloroimidazole compound Chemical class 0.000 claims description 23
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
- KVHFHTYQBHRHLJ-UHFFFAOYSA-N 2-(2-bromo-1-chloroethenyl)-4,5-dichloro-1H-imidazole Chemical compound ClC=1N=C(NC1Cl)C(=CBr)Cl KVHFHTYQBHRHLJ-UHFFFAOYSA-N 0.000 claims description 6
- ZUIUGNQZTRYYDZ-UHFFFAOYSA-N 4,5-dichloro-2-(1-chloroethenyl)-1h-imidazole Chemical compound ClC(=C)C1=NC(Cl)=C(Cl)N1 ZUIUGNQZTRYYDZ-UHFFFAOYSA-N 0.000 claims description 6
- LEVGHAATMPSLMN-UHFFFAOYSA-N 4,5-dichloro-2-(1,2-dichloroethenyl)-1H-imidazole Chemical compound ClC=1N=C(NC1Cl)C(=CCl)Cl LEVGHAATMPSLMN-UHFFFAOYSA-N 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- HOHUJKXBTNXMSZ-UHFFFAOYSA-N 4,5-dichloro-2-(2,2-dichloroethenyl)-1h-imidazole Chemical compound ClC(Cl)=CC1=NC(Cl)=C(Cl)N1 HOHUJKXBTNXMSZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 2
- 229910052727 yttrium Inorganic materials 0.000 claims description 2
- 101150009274 nhr-1 gene Proteins 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 79
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 48
- 238000006243 chemical reaction Methods 0.000 description 47
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 45
- 239000000203 mixture Substances 0.000 description 43
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 39
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 37
- 239000003795 chemical substances by application Substances 0.000 description 35
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 32
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 239000003085 diluting agent Substances 0.000 description 27
- 239000000243 solution Substances 0.000 description 27
- 239000007795 chemical reaction product Substances 0.000 description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
- 238000002844 melting Methods 0.000 description 23
- 230000008018 melting Effects 0.000 description 23
- 238000001816 cooling Methods 0.000 description 22
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 22
- 239000002904 solvent Substances 0.000 description 22
- 239000007858 starting material Substances 0.000 description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 229960001701 chloroform Drugs 0.000 description 16
- 235000009518 sodium iodide Nutrition 0.000 description 15
- 238000000354 decomposition reaction Methods 0.000 description 14
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- PQAMFDRRWURCFQ-UHFFFAOYSA-N 2-ethyl-1h-imidazole Chemical compound CCC1=NC=CN1 PQAMFDRRWURCFQ-UHFFFAOYSA-N 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 12
- 239000013078 crystal Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 9
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- YZXNUSFREIVOLU-UHFFFAOYSA-N 1-(4,5-dichloro-1h-imidazol-2-yl)ethanone Chemical compound CC(=O)C1=NC(Cl)=C(Cl)N1 YZXNUSFREIVOLU-UHFFFAOYSA-N 0.000 description 8
- KONUFEDJPWAJFJ-UHFFFAOYSA-N 4,5-dichloro-2-ethynyl-1h-imidazole Chemical compound ClC=1N=C(C#C)NC=1Cl KONUFEDJPWAJFJ-UHFFFAOYSA-N 0.000 description 8
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 8
- 239000003638 chemical reducing agent Substances 0.000 description 8
- 230000002363 herbicidal effect Effects 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- NVIFVTYDZMXWGX-UHFFFAOYSA-N sodium metaborate Chemical compound [Na+].[O-]B=O NVIFVTYDZMXWGX-UHFFFAOYSA-N 0.000 description 8
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 8
- OHWPJJSEYPMDRU-UHFFFAOYSA-N 2,4,5-trichloro-2-(1,1-dichloroethyl)imidazole Chemical compound CC(Cl)(Cl)C1(Cl)N=C(Cl)C(Cl)=N1 OHWPJJSEYPMDRU-UHFFFAOYSA-N 0.000 description 7
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 230000006378 damage Effects 0.000 description 7
- 235000019253 formic acid Nutrition 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- SOSFZRABIFHKBM-UHFFFAOYSA-N 4,5-dichloro-2-(1,1,2,2,2-pentachloroethyl)-1h-imidazole Chemical compound ClC=1N=C(C(Cl)(Cl)C(Cl)(Cl)Cl)NC=1Cl SOSFZRABIFHKBM-UHFFFAOYSA-N 0.000 description 6
- SLMLSJACRDWSRP-UHFFFAOYSA-N 4,5-dichloro-2-(1-iodoethenyl)-1H-imidazole Chemical compound ClC=1N=C(NC1Cl)C(=C)I SLMLSJACRDWSRP-UHFFFAOYSA-N 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 229910000039 hydrogen halide Inorganic materials 0.000 description 6
- 239000012433 hydrogen halide Substances 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 229940086542 triethylamine Drugs 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- 239000004280 Sodium formate Substances 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 5
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 5
- 235000019254 sodium formate Nutrition 0.000 description 5
- 239000012258 stirred mixture Substances 0.000 description 5
- RZFUADWCPSIYQY-UHFFFAOYSA-N 4,5-dichloro-2-(1,1,2,2-tetrachloroethyl)-1h-imidazole Chemical compound ClC(Cl)C(Cl)(Cl)C1=NC(Cl)=C(Cl)N1 RZFUADWCPSIYQY-UHFFFAOYSA-N 0.000 description 4
- NWWRAMOWAAGQAH-UHFFFAOYSA-N 4,5-dichloro-2-(2,2,2-trichloroethyl)-1h-imidazole Chemical compound ClC=1N=C(CC(Cl)(Cl)Cl)NC=1Cl NWWRAMOWAAGQAH-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000005864 Sulphur Substances 0.000 description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229910001513 alkali metal bromide Inorganic materials 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-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
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 229910001616 alkaline earth metal bromide Inorganic materials 0.000 description 3
- 229910001619 alkaline earth metal iodide Inorganic materials 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 239000012320 chlorinating reagent Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
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- 229910052987 metal hydride Inorganic materials 0.000 description 3
- 150000004681 metal hydrides Chemical class 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- YKKDKYKWZFYLIM-UHFFFAOYSA-N 4,5-dichloro-n-ethyl-1h-imidazole-2-carboxamide Chemical compound CCNC(=O)C1=NC(Cl)=C(Cl)N1 YKKDKYKWZFYLIM-UHFFFAOYSA-N 0.000 description 2
- 235000005781 Avena Nutrition 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
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- 239000004606 Fillers/Extenders Substances 0.000 description 2
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- 241000219146 Gossypium Species 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
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- 239000004480 active ingredient Substances 0.000 description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
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- 150000001447 alkali salts Chemical class 0.000 description 2
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- 239000007864 aqueous solution Substances 0.000 description 2
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- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
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- 239000012043 crude product Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 230000000382 dechlorinating effect Effects 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- 238000001914 filtration Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
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- 235000009973 maize Nutrition 0.000 description 2
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- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 2
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
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- 229920006395 saturated elastomer Polymers 0.000 description 2
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- 235000012239 silicon dioxide Nutrition 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/68—Halogen 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
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2901862.0 | 1979-01-18 | ||
| DE19792901862 DE2901862A1 (de) | 1979-01-18 | 1979-01-18 | 4,5-dichlorimidazol-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1135703A true CA1135703A (en) | 1982-11-16 |
Family
ID=6060864
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000343849A Expired CA1135703A (en) | 1979-01-18 | 1980-01-17 | 4,5-dichloroimidazole derivatives, processes for their preparation and their use as herbicides |
Country Status (15)
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1567084A1 (de) * | 1963-07-01 | 1970-10-15 | Shell Int Research | Mittel zur Bekaempfung unerwuenschten Pflanzenwuchses |
| DE1926206A1 (de) * | 1969-05-22 | 1970-11-26 | Bayer Ag | Verfahren zur Herstellung von Acylimidazolen |
| DE2610527A1 (de) * | 1976-03-12 | 1977-09-29 | Bayer Ag | 4,5-dichlorimidazol-2-carbonsaeurederivate, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide, fungizide und wachstumsregulatoren |
-
1979
- 1979-01-18 DE DE19792901862 patent/DE2901862A1/de not_active Withdrawn
-
1980
- 1980-01-10 EP EP80100105A patent/EP0013905B1/de not_active Expired
- 1980-01-10 AT AT80100105T patent/ATE966T1/de not_active IP Right Cessation
- 1980-01-10 PT PT70683A patent/PT70683A/pt unknown
- 1980-01-10 DE DE8080100105T patent/DE3060344D1/de not_active Expired
- 1980-01-15 IL IL59129A patent/IL59129A0/xx unknown
- 1980-01-16 DD DD80218486A patent/DD148582A5/de unknown
- 1980-01-17 BR BR8000295A patent/BR8000295A/pt unknown
- 1980-01-17 ZA ZA00800292A patent/ZA80292B/xx unknown
- 1980-01-17 PL PL22145380A patent/PL221453A1/xx unknown
- 1980-01-17 DK DK21080A patent/DK21080A/da unknown
- 1980-01-17 CA CA000343849A patent/CA1135703A/en not_active Expired
- 1980-01-17 ES ES487791A patent/ES487791A1/es not_active Expired
- 1980-01-17 AU AU54677/80A patent/AU5467780A/en not_active Abandoned
- 1980-01-18 CS CS80369A patent/CS209945B2/cs unknown
- 1980-01-18 JP JP372580A patent/JPS55100370A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP0013905B1 (de) | 1982-05-05 |
| IL59129A0 (en) | 1980-05-30 |
| CS209945B2 (en) | 1981-12-31 |
| PL221453A1 (enrdf_load_stackoverflow) | 1980-12-15 |
| JPS55100370A (en) | 1980-07-31 |
| DD148582A5 (de) | 1981-06-03 |
| ATE966T1 (de) | 1982-05-15 |
| EP0013905A1 (de) | 1980-08-06 |
| AU5467780A (en) | 1980-07-24 |
| ZA80292B (en) | 1981-01-28 |
| DK21080A (da) | 1980-07-19 |
| DE2901862A1 (de) | 1980-07-31 |
| ES487791A1 (es) | 1980-06-16 |
| BR8000295A (pt) | 1980-10-21 |
| DE3060344D1 (en) | 1982-06-24 |
| PT70683A (en) | 1980-02-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |