HU188126B - Herbicide compositions containing heterocylic phenyl etheres as activa substances and process for preparing the active substances - Google Patents
Herbicide compositions containing heterocylic phenyl etheres as activa substances and process for preparing the active substances Download PDFInfo
- Publication number
- HU188126B HU188126B HU80830A HU83080A HU188126B HU 188126 B HU188126 B HU 188126B HU 80830 A HU80830 A HU 80830A HU 83080 A HU83080 A HU 83080A HU 188126 B HU188126 B HU 188126B
- Authority
- HU
- Hungary
- Prior art keywords
- alkyl
- formula
- oxygen
- halogen
- hydrogen
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 26
- 230000002363 herbicidal effect Effects 0.000 title claims description 6
- 239000004009 herbicide Substances 0.000 title abstract description 3
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000013543 active substance Substances 0.000 title description 2
- 239000000126 substance Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 11
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- -1 alkali metal cation Chemical class 0.000 claims description 20
- 239000004480 active ingredient Substances 0.000 claims description 19
- 239000000460 chlorine Substances 0.000 claims description 18
- 239000001301 oxygen Substances 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 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 claims description 8
- 229910052708 sodium Inorganic materials 0.000 claims description 8
- 239000011734 sodium Substances 0.000 claims description 8
- 150000002367 halogens Chemical group 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000011593 sulfur Chemical group 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 239000000080 wetting agent Substances 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
- 206010029897 Obsessive thoughts Diseases 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000002270 dispersing agent Substances 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 239000003995 emulsifying agent Substances 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 2
- 238000009736 wetting Methods 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- UCIGDPVPVGGSGB-UHFFFAOYSA-N 4-(1H-indol-2-yloxy)phenol Chemical class C1=CC(O)=CC=C1OC1=CC2=CC=CC=C2N1 UCIGDPVPVGGSGB-UHFFFAOYSA-N 0.000 claims 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 3
- 101100072620 Streptomyces griseus ind2 gene Proteins 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004966 cyanoalkyl group Chemical group 0.000 abstract 1
- 150000002923 oximes Chemical class 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 238000009472 formulation Methods 0.000 description 10
- 241000196324 Embryophyta Species 0.000 description 8
- 239000008187 granular material Substances 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 5
- 239000004495 emulsifiable concentrate Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 244000000626 Daucus carota Species 0.000 description 3
- 235000002767 Daucus carota Nutrition 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000000227 grinding Methods 0.000 description 3
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical class CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 2
- 241000209504 Poaceae Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 230000009931 harmful effect Effects 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 229920005610 lignin Polymers 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000001117 oleyl group Polymers [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- JOXBFDPBVQGJOJ-UHFFFAOYSA-N 2,5-dichloro-1,3-benzoxazole Chemical compound ClC1=CC=C2OC(Cl)=NC2=C1 JOXBFDPBVQGJOJ-UHFFFAOYSA-N 0.000 description 1
- AJHZQRKIEBTEHH-UHFFFAOYSA-N 2-[4-[(6-chloro-1,3-benzothiazol-2-yl)oxy]phenoxy]propanoyl chloride Chemical compound C1=CC(OC(C)C(Cl)=O)=CC=C1OC1=NC2=CC=C(Cl)C=C2S1 AJHZQRKIEBTEHH-UHFFFAOYSA-N 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- GJBZOXPETBHOBL-UHFFFAOYSA-N 2-hydroxy-2-methyl-3-oxopentanoic acid Chemical compound CCC(=O)C(C)(O)C(O)=O GJBZOXPETBHOBL-UHFFFAOYSA-N 0.000 description 1
- SKOJDOXPRSFZMQ-UHFFFAOYSA-N 4-(1,3-benzothiazol-2-yloxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=NC2=CC=CC=C2S1 SKOJDOXPRSFZMQ-UHFFFAOYSA-N 0.000 description 1
- 241000209136 Agropyron Species 0.000 description 1
- 241000743985 Alopecurus Species 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 241000339490 Brachyachne Species 0.000 description 1
- 101100459917 Caenorhabditis elegans cnd-1 gene Proteins 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 244000052363 Cynodon dactylon Species 0.000 description 1
- 241000192043 Echinochloa Species 0.000 description 1
- 241000380130 Ehrharta erecta Species 0.000 description 1
- 241000508725 Elymus repens Species 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- IJMWOMHMDSDKGK-UHFFFAOYSA-N Isopropyl propionate Chemical compound CCC(=O)OC(C)C IJMWOMHMDSDKGK-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000209082 Lolium Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 239000006004 Quartz sand Substances 0.000 description 1
- 235000005775 Setaria Nutrition 0.000 description 1
- 241000232088 Setaria <nematode> Species 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 240000002439 Sorghum halepense Species 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 235000021186 dishes Nutrition 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052622 kaolinite Inorganic materials 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- FJUODKRZBACLQE-UHFFFAOYSA-N methyl 2-hydroxy-4-(4-hydroxyphenoxy)-3-oxopentanoate Chemical compound COC(=O)C(O)C(=O)C(C)OC1=CC=C(O)C=C1 FJUODKRZBACLQE-UHFFFAOYSA-N 0.000 description 1
- MKIJJIMOAABWGF-UHFFFAOYSA-N methyl 2-sulfanylacetate Chemical compound COC(=O)CS MKIJJIMOAABWGF-UHFFFAOYSA-N 0.000 description 1
- DWRXXMBKVSZQFV-UHFFFAOYSA-N methyl 3-oxo-2-sulfanylpentanoate Chemical compound CCC(=O)C(S)C(=O)OC DWRXXMBKVSZQFV-UHFFFAOYSA-N 0.000 description 1
- HUKZXLFXWLXYLG-UHFFFAOYSA-N methyl 4-[4-[(6-chloro-1,3-benzothiazol-2-yl)oxy]phenoxy]-3-oxo-2-sulfanylpentanoate Chemical compound C1=CC(OC(C)C(=O)C(S)C(=O)OC)=CC=C1OC1=NC2=CC=C(Cl)C=C2S1 HUKZXLFXWLXYLG-UHFFFAOYSA-N 0.000 description 1
- BVVGSKMVXMRYOH-UHFFFAOYSA-N methyl 4-bromo-2-hydroxy-2-methyl-3-oxopentanoate Chemical compound COC(=O)C(C)(O)C(=O)C(C)Br BVVGSKMVXMRYOH-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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 in position 2
-
- 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
- A01N43/52—1,3-Diazoles; Hydrogenated 1,3-diazoles condensed with carbocyclic rings, e.g. benzimidazoles
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/26—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2914300A DE2914300A1 (de) | 1979-04-09 | 1979-04-09 | Heterocyclische phenylether und diese enthaltende herbizide mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU188126B true HU188126B (en) | 1986-03-28 |
Family
ID=6067867
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU80830A HU188126B (en) | 1979-04-09 | 1980-04-08 | Herbicide compositions containing heterocylic phenyl etheres as activa substances and process for preparing the active substances |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4482373A (en, 2012) |
| JP (1) | JPS55141475A (en, 2012) |
| AR (1) | AR224262A1 (en, 2012) |
| AU (1) | AU536078B2 (en, 2012) |
| BE (1) | BE882705A (en, 2012) |
| BG (1) | BG31476A3 (en, 2012) |
| BR (1) | BR8002151A (en, 2012) |
| CA (1) | CA1148958A (en, 2012) |
| CH (1) | CH646160A5 (en, 2012) |
| DD (1) | DD149993A5 (en, 2012) |
| ES (1) | ES8107193A1 (en, 2012) |
| FR (1) | FR2453858A1 (en, 2012) |
| GB (1) | GB2046753B (en, 2012) |
| GR (1) | GR67685B (en, 2012) |
| HU (1) | HU188126B (en, 2012) |
| IL (1) | IL59782A (en, 2012) |
| IT (1) | IT1147343B (en, 2012) |
| KE (1) | KE3362A (en, 2012) |
| MA (1) | MA18807A1 (en, 2012) |
| NL (1) | NL8002060A (en, 2012) |
| PL (1) | PL223326A1 (en, 2012) |
| PT (1) | PT71068A (en, 2012) |
| SU (1) | SU963465A3 (en, 2012) |
| ZA (1) | ZA802065B (en, 2012) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GR67685B (en, 2012) * | 1979-04-09 | 1981-09-04 | Hoechst Ag | |
| DE3115152A1 (de) * | 1981-04-15 | 1982-12-02 | Hoechst Ag, 6000 Frankfurt | "heterocyclische phenylether und diese enthaltende herbizide mittel" |
| US4522647A (en) * | 1982-07-30 | 1985-06-11 | Zoecon Corporation | Substituted phenoxyalkanediones and their herbicidal method of use |
| DE3236730A1 (de) * | 1982-10-04 | 1984-04-05 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von benzoxazolyl- und benzthiazolyloxyphenoxypropionsaeurederivaten |
| JPS6092277A (ja) * | 1983-10-25 | 1985-05-23 | Nippon Tokushu Noyaku Seizo Kk | 置換フエノキシアルカンカルボン酸エステル，その製法及び除草剤 |
| GB8619236D0 (en) * | 1986-08-06 | 1986-09-17 | Ici Plc | Fungicides |
| EP0312064B1 (en) * | 1987-10-16 | 1994-05-04 | Kumiai Chemical Industry Co., Ltd. | Thiadiazabicyclononane derivatives and herbicidal compositions |
| US4954161A (en) * | 1989-01-09 | 1990-09-04 | American Cyanamid Company | Herbicidal composition and method for safening gramineous crops against heterocyclic phenyl ethers |
| AU6540490A (en) * | 1989-10-05 | 1991-04-28 | Hoechst Aktiengesellschaft | Herbicidal, heterocyclically substituted phenoxyalkane carboxylic acid derivatives and process for preparing them |
| DE69206299T2 (de) * | 1991-03-29 | 1996-03-28 | Tokuyama Corp | Cyanoketonderivat und dieses als Wirkstoff enthaltendes Herbizid. |
| JPH06179646A (ja) * | 1992-12-15 | 1994-06-28 | Tokuyama Soda Co Ltd | シアノケトン誘導体 |
| CN114478425B (zh) * | 2022-01-17 | 2024-03-22 | 安徽宁亿泰科技有限公司 | 一种芳氧苯氧丙酸酯除草剂的合成方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1009421B (de) * | 1954-09-20 | 1957-05-29 | Boehringer Sohn Ingelheim | Herbizide Mittel |
| GB1041982A (en) * | 1963-09-30 | 1966-09-07 | Boots Pure Drug Co Ltd | Herbicidal compounds and compositions |
| DE2223894C3 (de) * | 1972-05-17 | 1981-07-23 | Hoechst Ag, 6000 Frankfurt | Herbizide Mittel auf Basis von Phenoxycarbonsäurederivaten |
| DE2623558C2 (de) * | 1976-05-26 | 1984-12-06 | Hoechst Ag, 6230 Frankfurt | 2-[4'-Phenoxy-phenoxy]propionsäure-Derivate, Verfahren zu ihrer Herstellung und sie enthaltende herbizide Mittel |
| DE2628384C2 (de) * | 1976-06-24 | 1984-09-27 | Hoechst Ag, 6230 Frankfurt | 2-(4-Phenoxyphenoxy)- bzw. 2-(4-Benzylphenoxy)-propionsäurederivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Pflanzenbehandlungsmittel |
| DE2640730C2 (de) * | 1976-09-10 | 1983-08-25 | Hoechst Ag, 6230 Frankfurt | Benzoxazolyloxy- und Benzothiazolyloxy-phenoxy-Verbindungen und diese enthaltende herbizide Mittel |
| EP0005501B1 (de) * | 1978-05-20 | 1981-11-25 | Bayer Ag | Heteroaryl-oxyessigsäureamide, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide |
| DE2830066A1 (de) * | 1978-07-08 | 1980-01-17 | Hoechst Ag | 4-oxyphenoxyalkansaeurederivate und diese enthaltende herbizide mittel |
| GR67685B (en, 2012) * | 1979-04-09 | 1981-09-04 | Hoechst Ag |
-
1980
- 1980-04-02 GR GR61615A patent/GR67685B/el unknown
- 1980-04-02 ES ES490262A patent/ES8107193A1/es not_active Expired
- 1980-04-03 ZA ZA00802065A patent/ZA802065B/xx unknown
- 1980-04-03 CH CH264480A patent/CH646160A5/de not_active IP Right Cessation
- 1980-04-04 BG BG047244A patent/BG31476A3/xx unknown
- 1980-04-04 IT IT21222/80A patent/IT1147343B/it active
- 1980-04-07 DD DD80220248A patent/DD149993A5/de unknown
- 1980-04-07 AR AR280574A patent/AR224262A1/es active
- 1980-04-08 PL PL22332680A patent/PL223326A1/xx unknown
- 1980-04-08 JP JP4529580A patent/JPS55141475A/ja active Granted
- 1980-04-08 BR BR8002151A patent/BR8002151A/pt unknown
- 1980-04-08 HU HU80830A patent/HU188126B/hu unknown
- 1980-04-08 PT PT71068A patent/PT71068A/pt unknown
- 1980-04-08 NL NL8002060A patent/NL8002060A/nl not_active Application Discontinuation
- 1980-04-08 SU SU802903454A patent/SU963465A3/ru active
- 1980-04-08 IL IL59782A patent/IL59782A/xx unknown
- 1980-04-08 CA CA000349320A patent/CA1148958A/en not_active Expired
- 1980-04-09 BE BE0/200163A patent/BE882705A/fr not_active IP Right Cessation
- 1980-04-09 AU AU57276/80A patent/AU536078B2/en not_active Ceased
- 1980-04-09 FR FR8007941A patent/FR2453858A1/fr active Granted
- 1980-04-09 GB GB8011678A patent/GB2046753B/en not_active Expired
- 1980-04-09 MA MA19002A patent/MA18807A1/fr unknown
-
1983
- 1983-09-07 US US06/529,923 patent/US4482373A/en not_active Expired - Fee Related
-
1984
- 1984-01-11 KE KE3362A patent/KE3362A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US4482373A (en) | 1984-11-13 |
| ES490262A0 (es) | 1981-10-16 |
| GR67685B (en, 2012) | 1981-09-04 |
| JPH0140831B2 (en, 2012) | 1989-08-31 |
| CH646160A5 (de) | 1984-11-15 |
| PT71068A (en) | 1980-05-01 |
| BE882705A (fr) | 1980-10-09 |
| ZA802065B (en) | 1981-04-29 |
| IL59782A (en) | 1984-05-31 |
| BR8002151A (pt) | 1980-11-25 |
| DD149993A5 (de) | 1981-08-12 |
| PL223326A1 (en, 2012) | 1981-02-13 |
| MA18807A1 (fr) | 1980-12-31 |
| AR224262A1 (es) | 1981-11-13 |
| GB2046753B (en) | 1983-05-25 |
| AU536078B2 (en) | 1984-04-19 |
| BG31476A3 (en) | 1982-01-15 |
| IT1147343B (it) | 1986-11-19 |
| IL59782A0 (en) | 1980-06-30 |
| GB2046753A (en) | 1980-11-19 |
| FR2453858A1 (fr) | 1980-11-07 |
| FR2453858B1 (en, 2012) | 1983-08-12 |
| SU963465A3 (ru) | 1982-09-30 |
| JPS55141475A (en) | 1980-11-05 |
| ES8107193A1 (es) | 1981-10-16 |
| IT8021222A0 (it) | 1980-04-04 |
| CA1148958A (en) | 1983-06-28 |
| AU5727680A (en) | 1980-10-16 |
| KE3362A (en) | 1984-02-03 |
| NL8002060A (nl) | 1980-10-13 |
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