EP0394324A1 - o-CARBOMETHOXYSULFONYLUREE HERBICIDE - Google Patents
o-CARBOMETHOXYSULFONYLUREE HERBICIDEInfo
- Publication number
- EP0394324A1 EP0394324A1 EP89900719A EP89900719A EP0394324A1 EP 0394324 A1 EP0394324 A1 EP 0394324A1 EP 89900719 A EP89900719 A EP 89900719A EP 89900719 A EP89900719 A EP 89900719A EP 0394324 A1 EP0394324 A1 EP 0394324A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- methyl
- amino
- iii
- methoxy
- compound
- 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.)
- Pending
Links
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 7
- 241000196324 Embryophyta Species 0.000 claims abstract description 23
- 239000000203 mixture Substances 0.000 claims description 21
- RSMUVYRMZCOLBH-UHFFFAOYSA-N metsulfuron methyl Chemical compound COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 RSMUVYRMZCOLBH-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 239000003085 diluting agent Substances 0.000 claims description 8
- 240000003133 Elaeis guineensis Species 0.000 claims description 4
- 235000001950 Elaeis guineensis Nutrition 0.000 claims description 4
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 claims description 4
- 239000004009 herbicide Substances 0.000 claims description 4
- 239000000575 pesticide Substances 0.000 claims description 3
- 240000007154 Coffea arabica Species 0.000 claims description 2
- 241000218631 Coniferophyta Species 0.000 claims description 2
- 240000008790 Musa x paradisiaca Species 0.000 claims description 2
- 235000018290 Musa x paradisiaca Nutrition 0.000 claims description 2
- 235000016213 coffee Nutrition 0.000 claims description 2
- 235000013353 coffee beverage Nutrition 0.000 claims description 2
- 230000000295 complement effect Effects 0.000 claims 2
- ZEKANFGSDXODPD-UHFFFAOYSA-N glyphosate-isopropylammonium Chemical group CC(C)N.OC(=O)CNCP(O)(O)=O ZEKANFGSDXODPD-UHFFFAOYSA-N 0.000 claims 1
- -1 methyl 2 - [[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl) amino] carbonyl] amino] sulfonyl] benzoate compound Chemical class 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 description 27
- 239000008187 granular material Substances 0.000 description 13
- 239000004615 ingredient Substances 0.000 description 10
- 238000009472 formulation Methods 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 229960000892 attapulgite Drugs 0.000 description 6
- 229910052625 palygorskite Inorganic materials 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 239000008188 pellet Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 238000005507 spraying Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000004563 wettable powder Substances 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 2
- YIVXMZJTEQBPQO-UHFFFAOYSA-N 2,4-DB Chemical compound OC(=O)CCCOC1=CC=C(Cl)C=C1Cl YIVXMZJTEQBPQO-UHFFFAOYSA-N 0.000 description 2
- 239000002794 2,4-DB Substances 0.000 description 2
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 2
- IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 description 2
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 2
- 240000000230 Chromolaena odorata Species 0.000 description 2
- 241001503024 Dicranopteris linearis Species 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical class CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 244000048459 Euphorbia cyathophora Species 0.000 description 2
- CAWXEEYDBZRFPE-UHFFFAOYSA-N Hexazinone Chemical compound O=C1N(C)C(N(C)C)=NC(=O)N1C1CCCCC1 CAWXEEYDBZRFPE-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
- 240000007171 Imperata cylindrica Species 0.000 description 2
- 240000006550 Lantana camara Species 0.000 description 2
- 240000005338 Melastoma malabathricum Species 0.000 description 2
- 241000572126 Nephrolepis biserrata Species 0.000 description 2
- 241001285515 Spermacoce alata Species 0.000 description 2
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
- 238000005054 agglomeration Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- SDIXRDNYIMOKSG-UHFFFAOYSA-L disodium methyl arsenate Chemical compound [Na+].[Na+].C[As]([O-])([O-])=O SDIXRDNYIMOKSG-UHFFFAOYSA-L 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000005243 fluidization Methods 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-O isopropylaminium Chemical compound CC(C)[NH3+] JJWLVOIRVHMVIS-UHFFFAOYSA-O 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 231100001184 nonphytotoxic Toxicity 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000012053 oil suspension Substances 0.000 description 2
- INFDPOAKFNIJBF-UHFFFAOYSA-N paraquat Chemical compound C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 INFDPOAKFNIJBF-UHFFFAOYSA-N 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 229910052903 pyrophyllite Inorganic materials 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000001488 sodium phosphate Substances 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- NDUPDOJHUQKPAG-UHFFFAOYSA-M 2,2-Dichloropropanoate Chemical compound CC(Cl)(Cl)C([O-])=O NDUPDOJHUQKPAG-UHFFFAOYSA-M 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- WSSAMLJXFBGUJI-UHFFFAOYSA-N 2-(phosphonomethylamino)acetic acid Chemical compound OC(=O)CNCP(O)(O)=O.OC(=O)CNCP(O)(O)=O WSSAMLJXFBGUJI-UHFFFAOYSA-N 0.000 description 1
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 1
- NXFQWRWXEYTOTK-UHFFFAOYSA-N 2-methyl-4-amino-6-methoxy-s-triazine Chemical compound COC1=NC(C)=NC(N)=N1 NXFQWRWXEYTOTK-UHFFFAOYSA-N 0.000 description 1
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 1
- CDOUZKKFHVEKRI-UHFFFAOYSA-N 3-bromo-n-[(prop-2-enoylamino)methyl]propanamide Chemical compound BrCCC(=O)NCNC(=O)C=C CDOUZKKFHVEKRI-UHFFFAOYSA-N 0.000 description 1
- RHPUJHQBPORFGV-UHFFFAOYSA-N 4-chloro-2-methylphenol Chemical compound CC1=CC(Cl)=CC=C1O RHPUJHQBPORFGV-UHFFFAOYSA-N 0.000 description 1
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241001563787 Calopogonium Species 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 241000770293 Cenchrus pedicellatus Species 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 241001655719 Clidemia Species 0.000 description 1
- 244000033714 Clidemia hirta Species 0.000 description 1
- 235000014277 Clidemia hirta Nutrition 0.000 description 1
- NDUPDOJHUQKPAG-UHFFFAOYSA-N Dalapon Chemical compound CC(Cl)(Cl)C(O)=O NDUPDOJHUQKPAG-UHFFFAOYSA-N 0.000 description 1
- 239000005510 Diuron Substances 0.000 description 1
- 239000005561 Glufosinate Substances 0.000 description 1
- 239000005562 Glyphosate Substances 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000005584 Metsulfuron-methyl Substances 0.000 description 1
- 241001440840 Mikania micrantha Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000005595 Picloram Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 239000004965 Silica aerogel Substances 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 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
- 229940100389 Sulfonylurea Drugs 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- 239000005627 Triclopyr Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 241001148683 Zostera marina Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 208000014347 autosomal dominant hyaline body myopathy Diseases 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 229940097068 glyphosate Drugs 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- HVQWYKPSNHGIDD-UHFFFAOYSA-N methyl 2-isocyanatosulfonylbenzoate Chemical compound COC(=O)C1=CC=CC=C1S(=O)(=O)N=C=O HVQWYKPSNHGIDD-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- JITOKQVGRJSHHA-UHFFFAOYSA-M monosodium methyl arsenate Chemical compound [Na+].C[As](O)([O-])=O JITOKQVGRJSHHA-UHFFFAOYSA-M 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 235000020030 perry Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- NQQVFXUMIDALNH-UHFFFAOYSA-N picloram Chemical compound NC1=C(Cl)C(Cl)=NC(C(O)=O)=C1Cl NQQVFXUMIDALNH-UHFFFAOYSA-N 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910002029 synthetic silica gel Inorganic materials 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- NRZWQKGABZFFKE-UHFFFAOYSA-N trimethylsulfonium Chemical class C[S+](C)C NRZWQKGABZFFKE-UHFFFAOYSA-N 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene 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
- 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<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
Definitions
- This invention pertains to the use of the compound of Formula I and its agriculturally suitable salts for broad spectrum weed control in plantation crops.
- the compound is methyl 2-[H[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]amino]-sulfonyl]benzoate.
- Useful formulations of the compound of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly.
- Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare.
- High strength compositions are primarily used as intermediates for further formulation.
- the formulations broadly, contain about 0.1% to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 1% to 99.9% solid or liquid diluent(s). More specifically, they will contain these ingredients in the following approximate proportions:
- Active ingredient plus at least one of a Surfactant or a Diluent equals 100 weight percent.
- Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are sometimes desirable, and are achieved by incorporation into the formulation or by tank mixing.
- Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed * , Dorland Books, Caldwell, New Jersey, but other solids, either mined or manufactured, may be used. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts.
- Typical liquid diluents and solvents are described in Marsden, “Solvents Guide,” 2nd Ed., Interscience, New York, 1950. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0oC.
- compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Patent 3,060,084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See
- the ingredients are blended, coarsely hammermilled and then air-milled to produce particles essentially all below 10 microns in diameter.
- the product is reblended before packaging.
- the ingredients are blended, hammer-milled and then moistened with about 12% water.
- the mixture is extruded as cylinders about 3 mm diameter which are cut to produce pellets about 3 mm long. These may be used directly after drying, or the dried pellets may be crushed to pass a U.S.S. No. 20 sieve (0.84 mm openings).
- the granules held on a U.S.S. No. 40 sieve (0.42 mm openings) may be packaged for use and the fines recycled.
- Example 6 The active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a double cone blender. After spraying of the solution has been completed, the blender is allowed to run for a short period and then the granules are packaged.
- Example 6 The active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a double cone blender. After spraying of the solution has been completed, the blender is allowed to run for a short period and then the granules are packaged.
- Methyl 2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)- amino]carbonyl]amino]sulfonyl]benzoate 40% polyacrylic acid thickener 0.3% dodecylphenol polyethylene glycol ether 0.5% disodium phosphate 1% monosodium phosphate 0.5% polyvinyl alcohol 1.0% water 56.7%
- the ingredients are blended and ground together in a sand mill to produce particles essentially all under 5 microns in size.
- the ingredients are combined and ground together in a sand mill to produce particles essentially all below 5 microns.
- the product can be used directly, extended with oils, or emulsified in water.
- the ingredients are blended and ground in a hammer-mill to produce a material essentially all passing a U.S.S. No. 50 screen (0.3 mm opening).
- the concentrate may be formulated further if necessary.
- the ingredients are thoroughly blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in size.
- the material is reblended and then packaged.
- the active ingredient is blended with attapulgite and then passed through a hammer-mill to produce particles substantially all below 200 microns.
- the ground concentrate is then blended with powdered pyrophyllite until homogeneous.
- the compound of this invention can be specially formulated with diluents and/or carriers and/or other pesticides for application to plantation crops.
- the following list exemplifies some of the herbicides suitable for use in mixtures.
- Common Name Chemical Name dalapon 2,2-dichloropropionic acid diuron 3-(3,4-dichlorophenyl)-1,1-dimethylurea
- 2,4-DB 4-(2,4-dichlorophenoxy) butyric acid imazapyr- 2-(4-isopropyl-4-methyl-5-oxo-2-imida ⁇ isopropyl- zolin-2-yl)nicotinie acid with iso ⁇ ammonium propyl amine (1:1) picloram 4-amino-3,5,6-trichloropicolinic acid
- the compound employed in the method of the present invention is an active herbicide for selective broadleaf and grass weed control with safety to plantation crops such as coffee, cocoa, oil palm, rubber, banana, citrus and certain conifers.
- Compound I can be applied as a preemergence or postemergence treatment using techniques of banding, directed sprays or broadcast applications.
- the compound of this invention is used at 0.5 to 500 g/ha with a preferred rate range of 1 to 250 g/ha rate.
- One skilled in the art can select the proper rates for a given situation.
- the compound of this invention may be used in combination with other pesticides. It is particularly useful in combination with broadleaf herbicides used in plantation crops including: triazine, triazole, uracil, urea, amide, carbamate, bipyridylium, phenoxys, sulfonylurea and imidazolinone types.
- broadleaf herbicides used in plantation crops including: triazine, triazole, uracil, urea, amide, carbamate, bipyridylium, phenoxys, sulfonylurea and imidazolinone types.
- the preferred mixture for use in plantation crops includes glyphosate and its agriculturally suitable salts.
- Test A The herbicidal properties of the subject compound were discovered in field tests conducted as described below. Test A
- the weed species Calopogonium caerulium (A), Mikania micrantha (B) and Pagpgl ⁇ m coniuoatum (C) ranged in height from 10-20 cm up to mature plants and were sprayed with Compound I or its mixtures with Compounds II and III, dissolved in a nonphytotoxic solvent containing a surfactant.
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- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Un composé de méthyl 2-[[[[(4-méthoxy-6-méthyl-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulfonyl]benzoate présente une forte activité herbicide et est particulièrement utile pour éliminer les mauvaises herbes dans des cultures agricoles.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12530287A | 1987-11-25 | 1987-11-25 | |
| US125302 | 1987-11-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0394324A1 true EP0394324A1 (fr) | 1990-10-31 |
Family
ID=22419087
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP89900719A Pending EP0394324A1 (fr) | 1987-11-25 | 1988-11-23 | o-CARBOMETHOXYSULFONYLUREE HERBICIDE |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0394324A1 (fr) |
| JP (1) | JPH03501479A (fr) |
| AU (1) | AU613136B2 (fr) |
| BR (1) | BR8807812A (fr) |
| OA (1) | OA09626A (fr) |
| WO (1) | WO1989004606A1 (fr) |
| ZA (1) | ZA888856B (fr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5599769A (en) * | 1990-11-13 | 1997-02-04 | Hoechst Aktiengesellschaft | Synergistic herbicidal compositions comprising glyphosate or glufosinate in combination with a sulfonylurea herbicide |
| TW361993B (en) * | 1996-02-02 | 1999-06-21 | Nissan Chemical Ind Ltd | Herbicidal composition |
| JP3270819B2 (ja) * | 1997-02-13 | 2002-04-02 | 北興化学工業株式会社 | 湛水下水田の直接散布用水性懸濁製剤 |
| CN114403140A (zh) * | 2022-01-20 | 2022-04-29 | 上海启赟新材料有限公司 | 一种增稠稳定剂及其制备农药油悬浮剂的方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US438113A (en) * | 1890-10-07 | Island | ||
| DE2419737C3 (de) * | 1974-04-24 | 1978-07-20 | Licentia Patent-Verwaltungs-Gmbh, 6000 Frankfurt | Vorrichtung zum Vereinzeln von hintereinander auf einem Band befestigten flachen Gegenständen |
| US4383113A (en) * | 1978-05-30 | 1983-05-10 | E. I. Du Pont De Nemours And Company | Agricultural sulfonamides |
| DE2909834A1 (de) * | 1979-03-13 | 1980-09-18 | Gao Ges Automation Org | Verpackungselement fuer blattgut |
| DE2926340A1 (de) * | 1979-06-29 | 1981-02-05 | Sia Schweizer Schmirgel & Schl | Anordnung von schleifblaettern auf unterlagen und dispenser zur aufnahme und abgabe derartig angeordneter schleifblaetter |
| US4379717A (en) * | 1981-02-13 | 1983-04-12 | E. I. Du Pont De Nemours And Company | Method of controlling weeds in conifers |
-
1988
- 1988-11-23 JP JP1500559A patent/JPH03501479A/ja active Pending
- 1988-11-23 EP EP89900719A patent/EP0394324A1/fr active Pending
- 1988-11-23 AU AU28203/89A patent/AU613136B2/en not_active Ceased
- 1988-11-23 BR BR888807812A patent/BR8807812A/pt unknown
- 1988-11-23 WO PCT/US1988/004099 patent/WO1989004606A1/fr not_active Ceased
- 1988-11-25 ZA ZA888856A patent/ZA888856B/xx unknown
-
1990
- 1990-05-25 OA OA59794A patent/OA09626A/en unknown
Non-Patent Citations (1)
| Title |
|---|
| See references of WO8904606A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| AU613136B2 (en) | 1991-07-25 |
| WO1989004606A1 (fr) | 1989-06-01 |
| AU2820389A (en) | 1989-06-14 |
| BR8807812A (pt) | 1990-09-25 |
| JPH03501479A (ja) | 1991-04-04 |
| OA09626A (en) | 1993-04-30 |
| ZA888856B (en) | 1990-07-25 |
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