CS196225B2 - Herbicide and method of producing the active constituents - Google Patents
Herbicide and method of producing the active constituents Download PDFInfo
- Publication number
- CS196225B2 CS196225B2 CS778042A CS804277A CS196225B2 CS 196225 B2 CS196225 B2 CS 196225B2 CS 778042 A CS778042 A CS 778042A CS 804277 A CS804277 A CS 804277A CS 196225 B2 CS196225 B2 CS 196225B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- align
- acid
- compounds
- weeds
- acid catalyst
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 14
- 230000002363 herbicidal effect Effects 0.000 title claims description 13
- 239000004009 herbicide Substances 0.000 title abstract description 3
- 239000000470 constituent Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- 239000004480 active ingredient Substances 0.000 claims description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 13
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 12
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 11
- 239000003377 acid catalyst Substances 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 239000003849 aromatic solvent Substances 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 239000002798 polar solvent Substances 0.000 claims description 3
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical class NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 claims description 2
- NOJINLLSGYWYMM-UHFFFAOYSA-N 3-phenyl-1,3,5-oxadiazinan-4-one Chemical class O=C1NCOCN1C1=CC=CC=C1 NOJINLLSGYWYMM-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000005489 p-toluenesulfonic acid group Chemical group 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 abstract description 30
- 240000008042 Zea mays Species 0.000 abstract description 16
- 235000002017 Zea mays subsp mays Nutrition 0.000 abstract description 13
- 235000010469 Glycine max Nutrition 0.000 abstract description 10
- 235000021307 Triticum Nutrition 0.000 abstract description 10
- 244000299507 Gossypium hirsutum Species 0.000 abstract description 9
- 229920000742 Cotton Polymers 0.000 abstract description 8
- 240000007594 Oryza sativa Species 0.000 abstract description 8
- 235000007164 Oryza sativa Nutrition 0.000 abstract description 8
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 abstract description 8
- 235000005822 corn Nutrition 0.000 abstract description 8
- 244000068988 Glycine max Species 0.000 abstract description 7
- 244000105624 Arachis hypogaea Species 0.000 abstract description 6
- 230000006378 damage Effects 0.000 abstract description 6
- 235000009566 rice Nutrition 0.000 abstract description 6
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 abstract description 5
- 235000009973 maize Nutrition 0.000 abstract description 5
- 235000010777 Arachis hypogaea Nutrition 0.000 abstract description 3
- 244000098338 Triticum aestivum Species 0.000 abstract description 3
- 125000001309 chloro group Chemical group Cl* 0.000 abstract description 2
- 125000001153 fluoro group Chemical group F* 0.000 abstract description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 2
- 235000003276 Apios tuberosa Nutrition 0.000 abstract 1
- 235000010744 Arachis villosulicarpa Nutrition 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 239000013543 active substance Substances 0.000 description 12
- 241000209140 Triticum Species 0.000 description 9
- -1 polyoxymethylene Polymers 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 8
- 239000000654 additive Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 229930040373 Paraformaldehyde Natural products 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- 235000006463 Brassica alba Nutrition 0.000 description 5
- 244000140786 Brassica hirta Species 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000004495 emulsifiable concentrate Substances 0.000 description 5
- 239000000945 filler Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- 240000006694 Stellaria media Species 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 235000020232 peanut Nutrition 0.000 description 4
- 229920006324 polyoxymethylene Polymers 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- 240000002245 Acer pensylvanicum Species 0.000 description 3
- 235000006760 Acer pensylvanicum Nutrition 0.000 description 3
- 241000219312 Chenopodium Species 0.000 description 3
- 244000260524 Chrysanthemum balsamita Species 0.000 description 3
- 235000005633 Chrysanthemum balsamita Nutrition 0.000 description 3
- 235000017896 Digitaria Nutrition 0.000 description 3
- 241001303487 Digitaria <clam> Species 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 241000209082 Lolium Species 0.000 description 3
- 244000061458 Solanum melongena Species 0.000 description 3
- 235000007244 Zea mays Nutrition 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 244000038559 crop plants Species 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 230000035515 penetration Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- ILIKVSYOPGBFMA-UHFFFAOYSA-N 3-(3-chloro-4-propan-2-ylphenyl)-5-methyl-1,3,5-oxadiazinan-4-one Chemical compound C1=C(Cl)C(C(C)C)=CC=C1N1C(=O)N(C)COC1 ILIKVSYOPGBFMA-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 235000017060 Arachis glabrata Nutrition 0.000 description 2
- 235000018262 Arachis monticola Nutrition 0.000 description 2
- 235000011371 Brassica hirta Nutrition 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 208000003643 Callosities Diseases 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 244000058871 Echinochloa crus-galli Species 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 244000060234 Gmelina philippensis Species 0.000 description 2
- 206010020649 Hyperkeratosis Diseases 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 235000011999 Panicum crusgalli Nutrition 0.000 description 2
- 235000017016 Setaria faberi Nutrition 0.000 description 2
- 241001355178 Setaria faberi Species 0.000 description 2
- 235000002597 Solanum melongena Nutrition 0.000 description 2
- 244000061457 Solanum nigrum Species 0.000 description 2
- 235000002594 Solanum nigrum Nutrition 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 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 2
- 229920002866 paraformaldehyde Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000004546 suspension concentrate Substances 0.000 description 2
- 239000013008 thixotropic agent Substances 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- LYBCPJIYBPKTHI-UHFFFAOYSA-N 1,3,5-oxadiazinan-4-one Chemical class O=C1NCOCN1 LYBCPJIYBPKTHI-UHFFFAOYSA-N 0.000 description 1
- ZEICXCURVJGGCD-UHFFFAOYSA-N 1-(3-bromo-4-propan-2-ylphenyl)-3-methylurea Chemical compound CNC(=O)NC1=CC=C(C(C)C)C(Br)=C1 ZEICXCURVJGGCD-UHFFFAOYSA-N 0.000 description 1
- ZHFNUPJVYVQVLI-UHFFFAOYSA-N 2,3-dihydrooxadiazin-4-one Chemical compound O=C1NNOC=C1 ZHFNUPJVYVQVLI-UHFFFAOYSA-N 0.000 description 1
- WNLWIJRZMFZDNR-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-5-methyl-1,3,5-oxadiazinan-4-one Chemical compound O=C1N(C)COCN1C1=CC=C(Cl)C(Cl)=C1 WNLWIJRZMFZDNR-UHFFFAOYSA-N 0.000 description 1
- OWRGNAYEQMFUKQ-UHFFFAOYSA-N 3-(3-chloro-4-propan-2-ylphenyl)-1,1-dimethylurea Chemical compound CC(C)C1=CC=C(NC(=O)N(C)C)C=C1Cl OWRGNAYEQMFUKQ-UHFFFAOYSA-N 0.000 description 1
- 235000003911 Arachis Nutrition 0.000 description 1
- 244000075850 Avena orientalis Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 206010011878 Deafness Diseases 0.000 description 1
- 239000001692 EU approved anti-caking agent Substances 0.000 description 1
- 240000000047 Gossypium barbadense Species 0.000 description 1
- 235000009429 Gossypium barbadense Nutrition 0.000 description 1
- 235000009432 Gossypium hirsutum Nutrition 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 244000100545 Lolium multiflorum Species 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 241000723553 Pieris oleracea Species 0.000 description 1
- 235000005775 Setaria Nutrition 0.000 description 1
- 241000232088 Setaria <nematode> Species 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 241000207763 Solanum Species 0.000 description 1
- 235000002634 Solanum Nutrition 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000007798 antifreeze agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000002563 ionic surfactant Substances 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000008268 mayonnaise Substances 0.000 description 1
- 235000010746 mayonnaise Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 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 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000013074 reference sample Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- AZXQLMRILCCVDW-UHFFFAOYSA-M sodium;5-propan-2-ylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(C(C)C)=CC=CC2=C1S([O-])(=O)=O AZXQLMRILCCVDW-UHFFFAOYSA-M 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000004552 water soluble powder Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- 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
- A01N43/88—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 six-membered rings with three ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
- C07D273/02—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having two nitrogen atoms and only one oxygen atom
- C07D273/04—Six-membered rings
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material 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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7637543A FR2372815A1 (fr) | 1976-12-06 | 1976-12-06 | Nouveaux derives de la tetrahydro oxadiazine-1,3,5 one-4 et compositions herbicides les contenant |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS196225B2 true CS196225B2 (en) | 1980-03-31 |
Family
ID=9181005
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS778042A CS196225B2 (en) | 1976-12-06 | 1977-12-02 | Herbicide and method of producing the active constituents |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US4155747A (xx) |
| JP (1) | JPS5371090A (xx) |
| AR (1) | AR216929A1 (xx) |
| AU (1) | AU3118777A (xx) |
| BE (1) | BE861546A (xx) |
| BG (1) | BG28553A3 (xx) |
| BR (1) | BR7708107A (xx) |
| CA (1) | CA1088532A (xx) |
| CS (1) | CS196225B2 (xx) |
| DD (1) | DD136794A5 (xx) |
| DE (1) | DE2754238A1 (xx) |
| DK (1) | DK541577A (xx) |
| EG (1) | EG12860A (xx) |
| ES (1) | ES464423A1 (xx) |
| FR (1) | FR2372815A1 (xx) |
| GB (1) | GB1545715A (xx) |
| GR (1) | GR61618B (xx) |
| IE (1) | IE46176B1 (xx) |
| LU (1) | LU78633A1 (xx) |
| NL (1) | NL7713439A (xx) |
| OA (1) | OA05812A (xx) |
| PL (1) | PL107652B1 (xx) |
| SE (1) | SE7713849L (xx) |
| SU (1) | SU659067A3 (xx) |
| TR (1) | TR19486A (xx) |
| ZA (1) | ZA777214B (xx) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0549645U (ja) * | 1991-11-30 | 1993-06-29 | 須田産業株式会社 | 手提げ付フィルムバッグ |
| TW240163B (en) * | 1992-07-22 | 1995-02-11 | Syngenta Participations Ag | Oxadiazine derivatives |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1450485A (fr) * | 1964-04-30 | 1966-06-24 | Rohm & Haas | Tétrahydro-1. 3. 5-oxa-4-diazinones |
-
1976
- 1976-12-06 FR FR7637543A patent/FR2372815A1/fr active Granted
-
1977
- 1977-11-15 US US05/851,795 patent/US4155747A/en not_active Expired - Lifetime
- 1977-11-24 ES ES464423A patent/ES464423A1/es not_active Expired
- 1977-11-30 OA OA56327A patent/OA05812A/xx unknown
- 1977-12-02 AU AU31187/77A patent/AU3118777A/en active Pending
- 1977-12-02 IE IE2447/77A patent/IE46176B1/en unknown
- 1977-12-02 CS CS778042A patent/CS196225B2/cs unknown
- 1977-12-02 CA CA292,282A patent/CA1088532A/en not_active Expired
- 1977-12-02 GB GB50408/77A patent/GB1545715A/en not_active Expired
- 1977-12-03 EG EG663/77A patent/EG12860A/xx active
- 1977-12-05 SU SU772549602A patent/SU659067A3/ru active
- 1977-12-05 BG BG037952A patent/BG28553A3/xx unknown
- 1977-12-05 NL NL7713439A patent/NL7713439A/xx not_active Application Discontinuation
- 1977-12-05 PL PL1977202654A patent/PL107652B1/pl unknown
- 1977-12-05 LU LU78633A patent/LU78633A1/xx unknown
- 1977-12-05 GR GR54918A patent/GR61618B/el unknown
- 1977-12-05 ZA ZA00777214A patent/ZA777214B/xx unknown
- 1977-12-05 JP JP14598077A patent/JPS5371090A/ja active Pending
- 1977-12-05 DK DK541577A patent/DK541577A/da unknown
- 1977-12-05 AR AR270241A patent/AR216929A1/es active
- 1977-12-06 BE BE183203A patent/BE861546A/xx unknown
- 1977-12-06 DE DE19772754238 patent/DE2754238A1/de not_active Withdrawn
- 1977-12-06 DD DD77202435A patent/DD136794A5/xx unknown
- 1977-12-06 BR BR7708107A patent/BR7708107A/pt unknown
- 1977-12-06 SE SE7713849A patent/SE7713849L/xx not_active Application Discontinuation
- 1977-12-06 TR TR19486A patent/TR19486A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2754238A1 (de) | 1978-06-15 |
| DK541577A (da) | 1978-06-07 |
| BE861546A (fr) | 1978-06-06 |
| SU659067A3 (ru) | 1979-04-25 |
| US4155747A (en) | 1979-05-22 |
| AR216929A1 (es) | 1980-02-15 |
| ES464423A1 (es) | 1978-08-01 |
| IE46176B1 (en) | 1983-03-23 |
| TR19486A (tr) | 1979-04-17 |
| FR2372815A1 (fr) | 1978-06-30 |
| LU78633A1 (fr) | 1979-06-13 |
| DD136794A5 (de) | 1979-08-01 |
| BR7708107A (pt) | 1978-08-08 |
| SE7713849L (sv) | 1978-06-07 |
| CA1088532A (en) | 1980-10-28 |
| ZA777214B (en) | 1978-09-27 |
| GB1545715A (en) | 1979-05-16 |
| JPS5371090A (en) | 1978-06-24 |
| NL7713439A (nl) | 1978-06-08 |
| EG12860A (en) | 1981-03-31 |
| AU3118777A (en) | 1979-06-07 |
| PL202654A1 (pl) | 1978-10-23 |
| GR61618B (en) | 1978-12-04 |
| FR2372815B1 (xx) | 1979-04-06 |
| PL107652B1 (pl) | 1980-02-29 |
| BG28553A3 (bg) | 1980-05-15 |
| IE46176L (en) | 1978-06-06 |
| OA05812A (fr) | 1981-05-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4270946A (en) | N-Aryl,2-phenoxy nicotinamide compounds and the herbicidal use thereof | |
| US4278461A (en) | Herbicidal agents | |
| IE51408B1 (en) | New aniline derivatives | |
| US3238222A (en) | (n-3, 4-disubstituted phenyl-3 and/or omega methyl-2-pyrrolidinones and piperidones) | |
| EP0103537A2 (de) | N-Arylsulfonyl-N'-triazolylharnstoffe | |
| EP0300906B1 (en) | Novel 2-(substituted imino)-1,3,4-dihydrothiadiazoles | |
| PL170635B1 (pl) | Srodek chwastobójczy PL PL PL | |
| CZ244394A3 (en) | Herbicidal 1,2,4-oxadiazolecarboxylic acids amides, esters or halides | |
| US4867782A (en) | Novel herbicidal 2-sulfonyliminothiazolidines | |
| US4057417A (en) | 6-Sec.-butyl-1,2,4-triazin-5(4H)-one compounds and herbicidal compositions | |
| CS196225B2 (en) | Herbicide and method of producing the active constituents | |
| KR910006988B1 (ko) | 2-알콕시아미노설포닐벤젠-설포닐우레아의 제조방법 | |
| EP0196570B1 (en) | Benzoaxazine derivatives and herbicidal composition | |
| GB2103610A (en) | Herbicidal compounds derived from N-sulphonyl-aryloxybenamides and the processes for their preparation and use | |
| JPS63280060A (ja) | アルキル‐ｎ‐アリール‐テトラヒドロフタルイミド、それらの製造方法およびそれらの植物保護における用途 | |
| US4531966A (en) | Herbicide compositions | |
| KR920005411B1 (ko) | 치환된 테트라졸의 제법 | |
| AU647659B2 (en) | Iminothiazolines, their production and use as herbicides | |
| US4501605A (en) | Herbicidal heterocyclic compounds and compositions | |
| US4327218A (en) | N-Aryl, 2-phenoxy nicotinamide compounds and the herbicidal use thereof | |
| DK166495B1 (da) | Phenoxyphthalidderivater, en fremgangsmaade til fremstilling af saadanne forbindelser, herbicidpraeparater indeholdende saadanne forbindelser samt deres anvendelse ved bekaempelse af uoensket plantevaekst | |
| US5583092A (en) | Herbicidal [1,2,4] thiadiazoles | |
| CS207781B2 (en) | Herbicide means and method of making the active substances | |
| KR930011780B1 (ko) | 3-옥시미노 디페닐에테르 유도체의 제조방법 | |
| GB2027699A (en) | Substituted phenylurea |