CS208667B2 - Herbicide means and method of making the active substances - Google Patents
Herbicide means and method of making the active substances Download PDFInfo
- Publication number
- CS208667B2 CS208667B2 CS795106A CS510679A CS208667B2 CS 208667 B2 CS208667 B2 CS 208667B2 CS 795106 A CS795106 A CS 795106A CS 510679 A CS510679 A CS 510679A CS 208667 B2 CS208667 B2 CS 208667B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- trifluoromethyl
- compound
- plants
- active ingredient
- selectivity
- Prior art date
Links
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 13
- 239000004009 herbicide Substances 0.000 title abstract description 5
- 239000013543 active substance Substances 0.000 title description 8
- 238000004519 manufacturing process Methods 0.000 title 1
- 229920000742 Cotton Polymers 0.000 claims abstract description 8
- 240000008042 Zea mays Species 0.000 claims abstract description 7
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims abstract description 7
- 235000013339 cereals Nutrition 0.000 claims abstract description 6
- 244000068988 Glycine max Species 0.000 claims abstract description 5
- 235000010469 Glycine max Nutrition 0.000 claims abstract description 5
- 241000196324 Embryophyta Species 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 26
- -1 3-trifluoromethyl-4-ethylphenyl Chemical group 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 8
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 6
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims description 5
- 235000009973 maize Nutrition 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- NIDVHKJHHDBQGG-UHFFFAOYSA-N 1-ethyl-4-isocyanato-2-(trifluoromethyl)benzene Chemical compound FC(C=1C=C(C=CC1CC)N=C=O)(F)F NIDVHKJHHDBQGG-UHFFFAOYSA-N 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 244000299507 Gossypium hirsutum Species 0.000 claims 1
- 239000012050 conventional carrier Substances 0.000 claims 1
- 244000045561 useful plants Species 0.000 claims 1
- 241000219146 Gossypium Species 0.000 abstract description 6
- 239000000463 material Substances 0.000 abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 abstract description 2
- 235000005822 corn Nutrition 0.000 abstract description 2
- MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 38
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000004480 active ingredient Substances 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 9
- 238000011282 treatment Methods 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000005533 Fluometuron Substances 0.000 description 7
- 244000038559 crop plants Species 0.000 description 7
- RZILCCPWPBTYDO-UHFFFAOYSA-N fluometuron Chemical compound CN(C)C(=O)NC1=CC=CC(C(F)(F)F)=C1 RZILCCPWPBTYDO-UHFFFAOYSA-N 0.000 description 7
- 239000012263 liquid product Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- QWCSPEJQIACNGS-UHFFFAOYSA-N 4-ethyl-3-(trifluoromethyl)aniline Chemical compound CCC1=CC=C(N)C=C1C(F)(F)F QWCSPEJQIACNGS-UHFFFAOYSA-N 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- 239000000654 additive Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 235000013877 carbamide Nutrition 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- OXLCJYGDSPAMQS-UHFFFAOYSA-N 1-[4-ethyl-3-(trifluoromethyl)phenyl]-1,3-dimethylurea Chemical compound FC(C=1C=C(C=CC1CC)N(C(=O)NC)C)(F)F OXLCJYGDSPAMQS-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 241000209140 Triticum Species 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- 150000003672 ureas Chemical class 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 241000219198 Brassica Species 0.000 description 2
- 235000006463 Brassica alba Nutrition 0.000 description 2
- 235000003351 Brassica cretica Nutrition 0.000 description 2
- 244000140786 Brassica hirta Species 0.000 description 2
- 235000003343 Brassica rupestris Nutrition 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 240000006694 Stellaria media Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000003849 aromatic solvent Substances 0.000 description 2
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 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
- 239000000975 dye Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000005461 lubrication Methods 0.000 description 2
- 235000010460 mustard Nutrition 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000004546 suspension concentrate Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 1
- LGXVIGDEPROXKC-UHFFFAOYSA-N 1,1-dichloroethene Chemical compound ClC(Cl)=C LGXVIGDEPROXKC-UHFFFAOYSA-N 0.000 description 1
- MXDMRWOMPWYOBI-UHFFFAOYSA-N 1,3-dimethyl-1-[3-(trifluoromethyl)phenyl]urea Chemical compound CNC(=O)N(C)C1=CC=CC(C(F)(F)F)=C1 MXDMRWOMPWYOBI-UHFFFAOYSA-N 0.000 description 1
- YYZSSTIQGXZVMR-UHFFFAOYSA-N 1-[4-butyl-3-(trifluoromethyl)phenyl]-1-methylurea Chemical compound FC(C=1C=C(C=CC1CCCC)N(C(=O)N)C)(F)F YYZSSTIQGXZVMR-UHFFFAOYSA-N 0.000 description 1
- NLMURJDGDBEMAB-UHFFFAOYSA-N 3,3,3-trifluoropropylbenzene Chemical compound FC(F)(F)CCC1=CC=CC=C1 NLMURJDGDBEMAB-UHFFFAOYSA-N 0.000 description 1
- ZNRBAXFJYZDATD-UHFFFAOYSA-N 3-[4-ethyl-3-(trifluoromethyl)phenyl]-1,1-dimethylurea Chemical compound CCC1=C(C=C(NC(=O)N(C)C)C=C1)C(F)(F)F ZNRBAXFJYZDATD-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 235000007320 Avena fatua Nutrition 0.000 description 1
- 241000209764 Avena fatua Species 0.000 description 1
- 235000011371 Brassica hirta Nutrition 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000005494 Chlorotoluron Substances 0.000 description 1
- 206010011878 Deafness Diseases 0.000 description 1
- 244000152970 Digitaria sanguinalis Species 0.000 description 1
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
- 241001057636 Dracaena deremensis Species 0.000 description 1
- 239000001692 EU approved anti-caking agent Substances 0.000 description 1
- 244000058871 Echinochloa crus-galli Species 0.000 description 1
- OEIVANZXKKUBNP-UHFFFAOYSA-N FC(CCC1=CC=C(C=C1)[N+](=O)[O-])(F)F Chemical compound FC(CCC1=CC=C(C=C1)[N+](=O)[O-])(F)F OEIVANZXKKUBNP-UHFFFAOYSA-N 0.000 description 1
- 244000060234 Gmelina philippensis Species 0.000 description 1
- 240000000047 Gossypium barbadense Species 0.000 description 1
- 235000009429 Gossypium barbadense Nutrition 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 244000061458 Solanum melongena Species 0.000 description 1
- 235000002597 Solanum melongena Nutrition 0.000 description 1
- 244000061457 Solanum nigrum Species 0.000 description 1
- 235000002594 Solanum nigrum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 235000007244 Zea mays Nutrition 0.000 description 1
- YSVZGWAJIHWNQK-UHFFFAOYSA-N [3-(hydroxymethyl)-2-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1CC2C(CO)C(CO)C1C2 YSVZGWAJIHWNQK-UHFFFAOYSA-N 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 125000002252 acyl group Chemical group 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
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 238000004458 analytical method Methods 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
- 230000004071 biological effect Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- JXCGFZXSOMJFOA-UHFFFAOYSA-N chlorotoluron Chemical compound CN(C)C(=O)NC1=CC=C(C)C(Cl)=C1 JXCGFZXSOMJFOA-UHFFFAOYSA-N 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 230000001747 exhibiting effect Effects 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
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 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 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000008268 mayonnaise Substances 0.000 description 1
- 235000010746 mayonnaise Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 150000002828 nitro derivatives Chemical class 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
- 229940005483 opioid analgesics Drugs 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 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
- 239000012266 salt solution Substances 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/23—Preparation of halogenated hydrocarbons by dehalogenation
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
- C07C265/12—Derivatives of isocyanic acid having isocyanate groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/30—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by halogen atoms, or by nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Agronomy & Crop Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7822885A FR2435464A1 (fr) | 1978-07-25 | 1978-07-25 | Nouvelle phenyluree substituee herbicide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS208667B2 true CS208667B2 (en) | 1981-09-15 |
Family
ID=9211510
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS795106A CS208667B2 (en) | 1978-07-25 | 1979-07-20 | Herbicide means and method of making the active substances |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP0016132A1 (pt) |
| JP (1) | JPS55500454A (pt) |
| AU (1) | AU4913279A (pt) |
| CS (1) | CS208667B2 (pt) |
| DD (1) | DD145053A5 (pt) |
| DK (1) | DK122780A (pt) |
| ES (1) | ES8202790A1 (pt) |
| FR (1) | FR2435464A1 (pt) |
| GB (1) | GB2027699A (pt) |
| GR (1) | GR69974B (pt) |
| IL (1) | IL57758A0 (pt) |
| MA (1) | MA18537A1 (pt) |
| OA (1) | OA06494A (pt) |
| PL (1) | PL217326A1 (pt) |
| PT (1) | PT69964A (pt) |
| WO (1) | WO1980000344A1 (pt) |
| ZA (1) | ZA793754B (pt) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1981002240A1 (fr) * | 1980-02-05 | 1981-08-20 | Rhone Poulenc Agrochimie | Melanges herbicides utilisables pour le coton |
| DE3314249A1 (de) * | 1983-04-20 | 1984-10-25 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von fluorierten phenylessigsaeureestern und neue fluorierte trichlorethylbenzole |
| US4467125A (en) * | 1983-06-10 | 1984-08-21 | Monsanto Company | Nitro-methyl or ethyl substituted benzotrifluoride |
| BR9305817A (pt) | 1992-01-29 | 1995-12-26 | Basf Ag | Carbamato intermediario derivados de hidroxilamina composto fungicida e processo para combater fungos |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL31574A0 (en) * | 1968-02-13 | 1969-04-30 | Ciba Ltd | Use of certain ureas for combating weeds |
-
1978
- 1978-07-25 FR FR7822885A patent/FR2435464A1/fr not_active Withdrawn
-
1979
- 1979-07-09 IL IL57758A patent/IL57758A0/xx unknown
- 1979-07-13 ES ES482473A patent/ES8202790A1/es not_active Expired
- 1979-07-20 CS CS795106A patent/CS208667B2/cs unknown
- 1979-07-23 ZA ZA00793754A patent/ZA793754B/xx unknown
- 1979-07-23 PT PT69964A patent/PT69964A/pt unknown
- 1979-07-23 GB GB7925650A patent/GB2027699A/en not_active Withdrawn
- 1979-07-23 AU AU49132/79A patent/AU4913279A/en not_active Abandoned
- 1979-07-24 JP JP50117379A patent/JPS55500454A/ja active Pending
- 1979-07-24 MA MA18734A patent/MA18537A1/fr unknown
- 1979-07-24 WO PCT/FR1979/000068 patent/WO1980000344A1/fr not_active Ceased
- 1979-07-24 PL PL21732679A patent/PL217326A1/xx unknown
- 1979-07-24 DD DD79214581A patent/DD145053A5/de unknown
- 1979-07-25 GR GR59691A patent/GR69974B/el unknown
-
1980
- 1980-03-11 EP EP79900847A patent/EP0016132A1/fr not_active Withdrawn
- 1980-03-21 DK DK122780A patent/DK122780A/da unknown
- 1980-03-25 OA OA57062A patent/OA06494A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU4913279A (en) | 1980-01-31 |
| PL217326A1 (pt) | 1980-07-01 |
| ES482473A0 (es) | 1981-02-16 |
| JPS55500454A (pt) | 1980-07-24 |
| DK122780A (da) | 1980-03-21 |
| ES8202790A1 (es) | 1981-02-16 |
| DD145053A5 (de) | 1980-11-19 |
| OA06494A (fr) | 1981-08-31 |
| MA18537A1 (fr) | 1980-04-01 |
| WO1980000344A1 (fr) | 1980-03-06 |
| ZA793754B (en) | 1980-07-30 |
| GR69974B (pt) | 1982-07-22 |
| FR2435464A1 (fr) | 1980-04-04 |
| PT69964A (fr) | 1979-08-01 |
| EP0016132A1 (fr) | 1980-10-01 |
| GB2027699A (en) | 1980-02-27 |
| IL57758A0 (en) | 1979-11-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0641316B1 (en) | Insecticidal phenylhydrazine derivatives | |
| JPH0623164B2 (ja) | 殺害虫剤としての作用を有するベンゾイル尿素化合物 | |
| MXPA96005256A (en) | Aminofenilsulfonilureas aciladas, procedures for its preparation and its use as herbicides and plan growth regulators | |
| DK149448B (da) | N-phenyl-n'-(2-chlor-6-fluorbenzoyl)-urinstoffer, insecticidt middel indeholdende mindst en saadan forbindelse samt deres anvendelse til bekaempelse af insekter | |
| CS235957B2 (en) | Herbicide and plant growth regulation agent and method of its efficient component production | |
| CA1172637A (en) | Aniline derivatives | |
| EP0103537B1 (de) | N-Arylsulfonyl-N'-triazolylharnstoffe | |
| US3917478A (en) | Herbicidal compositions and methods utilizing thiadiazolis ureas | |
| JPH0421672B2 (pt) | ||
| CS208667B2 (en) | Herbicide means and method of making the active substances | |
| US5486521A (en) | Pyrimidinyl aryl ketone oximes | |
| KR910006988B1 (ko) | 2-알콕시아미노설포닐벤젠-설포닐우레아의 제조방법 | |
| CA1166250A (en) | Substituted tetrahydropyrimidinone derivatives, process for their preparation and their use as herbicides | |
| JPS63201152A (ja) | シクロヘキサンジオン及びその製造方法並びに該化合物を含有する農薬組成物 | |
| GB2103610A (en) | Herbicidal compounds derived from N-sulphonyl-aryloxybenamides and the processes for their preparation and use | |
| JPS6348248A (ja) | ベンゾヒドロキサム酸誘導体 | |
| JPH0453863B2 (pt) | ||
| US4257805A (en) | Herbicidal (4-substituted-phenylamino)-3-(trifluoromethyl)phenyl)ureas | |
| KR930011780B1 (ko) | 3-옥시미노 디페닐에테르 유도체의 제조방법 | |
| US4155747A (en) | Derivatives of tetrahydro-1,3,5-oxadiazin-4-one and herbicidal compositions containing these derivatives | |
| JP2696252B2 (ja) | シクロヘキサンカルボン酸誘導体並びにそれを含有する除草剤及び植物生長調節剤 | |
| NZ202387A (en) | Herbicidal arylphenyl ether derivatives | |
| SK85096A3 (en) | Fluoropropylthiazoline derivatives and herbicides | |
| US4259506A (en) | New 3-ureido-(thio)-chromone derivatives | |
| US3867429A (en) | Alkynyloxy)alkyl and (alkenyloxy)alkyl carbamates |