PT96606A - Processo para a preparacao de derivados de sulfonilureia substituidos herbicidamente activos e de composicoes herbicidas que os contem - Google Patents
Processo para a preparacao de derivados de sulfonilureia substituidos herbicidamente activos e de composicoes herbicidas que os contem Download PDFInfo
- Publication number
- PT96606A PT96606A PT96606A PT9660691A PT96606A PT 96606 A PT96606 A PT 96606A PT 96606 A PT96606 A PT 96606A PT 9660691 A PT9660691 A PT 9660691A PT 96606 A PT96606 A PT 96606A
- Authority
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- Portugal
- Prior art keywords
- active ingredient
- alkyl
- general formula
- formula
- compound
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 74
- 238000002360 preparation method Methods 0.000 title claims description 38
- 238000000034 method Methods 0.000 title claims description 29
- 230000002363 herbicidal effect Effects 0.000 title claims description 18
- 230000008569 process Effects 0.000 title claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 83
- 239000004480 active ingredient Substances 0.000 claims description 68
- 241000196324 Embryophyta Species 0.000 claims description 46
- -1 alkali metal salt Chemical class 0.000 claims description 41
- 239000000729 antidote Substances 0.000 claims description 38
- 239000002689 soil Substances 0.000 claims description 25
- 239000003795 chemical substances by application Substances 0.000 claims description 17
- 239000004563 wettable powder Substances 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 9
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 239000008187 granular material Substances 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical group 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- YRMLFORXOOIJDR-UHFFFAOYSA-N Dichlormid Chemical compound ClC(Cl)C(=O)N(CC=C)CC=C YRMLFORXOOIJDR-UHFFFAOYSA-N 0.000 claims description 6
- OHXLAOJLJWLEIP-UHFFFAOYSA-N 2-(dichloromethyl)-2-methyl-1,3-dioxolane Chemical compound ClC(Cl)C1(C)OCCO1 OHXLAOJLJWLEIP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 150000005005 aminopyrimidines Chemical class 0.000 claims description 5
- QQOWHRYOXYEMTL-UHFFFAOYSA-N triazin-4-amine Chemical class N=C1C=CN=NN1 QQOWHRYOXYEMTL-UHFFFAOYSA-N 0.000 claims description 5
- WFVUIONFJOAYPK-SDNWHVSQSA-N (z)-n-(1,3-dioxolan-2-ylmethoxy)benzenecarboximidoyl cyanide Chemical compound C=1C=CC=CC=1C(/C#N)=N/OCC1OCCO1 WFVUIONFJOAYPK-SDNWHVSQSA-N 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 238000001704 evaporation Methods 0.000 claims description 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 3
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 2
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 150000002540 isothiocyanates Chemical class 0.000 claims description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- HFFXLYHRNRKAPM-UHFFFAOYSA-N 2,4,5-trichloro-n-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C(=CC(Cl)=C(Cl)C=2)Cl)=N1 HFFXLYHRNRKAPM-UHFFFAOYSA-N 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 1
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
- 101150047265 COR2 gene Proteins 0.000 claims 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 1
- 101100467189 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) QCR2 gene Proteins 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 239000000843 powder Substances 0.000 description 21
- 238000011282 treatment Methods 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- 239000004546 suspension concentrate Substances 0.000 description 14
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 13
- 238000012360 testing method Methods 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000002270 dispersing agent Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000004094 surface-active agent Substances 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 240000008042 Zea mays Species 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- JYIMWRSJCRRYNK-UHFFFAOYSA-N dialuminum;disodium;oxygen(2-);silicon(4+);hydrate Chemical compound O.[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[Na+].[Na+].[Al+3].[Al+3].[Si+4] JYIMWRSJCRRYNK-UHFFFAOYSA-N 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229940100389 Sulfonylurea Drugs 0.000 description 8
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 241000209140 Triticum Species 0.000 description 7
- 235000021307 Triticum Nutrition 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 238000009331 sowing Methods 0.000 description 7
- 239000000080 wetting agent Substances 0.000 description 7
- ZAWPDPLWGKAAHU-UHFFFAOYSA-N 2,2-dichloro-n-[2-oxo-2-(prop-2-enylamino)ethyl]-n-prop-2-enylacetamide Chemical compound ClC(Cl)C(=O)N(CC=C)CC(=O)NCC=C ZAWPDPLWGKAAHU-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 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 6
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 6
- 239000007844 bleaching agent Substances 0.000 description 6
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- 244000062793 Sorghum vulgare Species 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 5
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 5
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- 229940082509 xanthan gum Drugs 0.000 description 5
- GXJQMKFJQFGQKV-KHPPLWFESA-N 2-[methyl-[(z)-octadec-9-enoyl]amino]ethanesulfonic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)N(C)CCS(O)(=O)=O GXJQMKFJQFGQKV-KHPPLWFESA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
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- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 4
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- 239000011734 sodium Substances 0.000 description 4
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- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 4
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- 239000008096 xylene Substances 0.000 description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 3
- LPVPNRSVMLNXGQ-UHFFFAOYSA-N 1-(azepan-1-yl)-2,2-dichloroethanone Chemical compound ClC(Cl)C(=O)N1CCCCCC1 LPVPNRSVMLNXGQ-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- 235000011684 Sorghum saccharatum Nutrition 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 3
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- 238000010521 absorption reaction Methods 0.000 description 3
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- 229910000278 bentonite Inorganic materials 0.000 description 3
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- 230000015572 biosynthetic process Effects 0.000 description 3
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- 150000002431 hydrogen Chemical class 0.000 description 3
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- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 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 description 3
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- WJXVCCKOBJRWSL-UHFFFAOYSA-N methyl 2-[[(4,6-dimethylpyrimidin-2-yl)-(ethoxymethyl)carbamoyl]sulfamoyl]benzoate Chemical compound CC1=NC(=NC(=C1)C)N(C(NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC)=O)COCC WJXVCCKOBJRWSL-UHFFFAOYSA-N 0.000 description 1
- XNKPPHVFIILXEZ-UHFFFAOYSA-N methyl 2-[[(4,6-dimethylpyrimidin-2-yl)-(methoxymethyl)carbamoyl]sulfamoyl]benzoate Chemical compound CC1=NC(=NC(=C1)C)N(C(NS(=O)(=O)C1=C(C=CC=C1)C(=O)OC)=O)COC XNKPPHVFIILXEZ-UHFFFAOYSA-N 0.000 description 1
- HUNUAFNLLYVTQD-UHFFFAOYSA-N methyl 2-chlorosulfonylbenzoate Chemical compound COC(=O)C1=CC=CC=C1S(Cl)(=O)=O HUNUAFNLLYVTQD-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- JUFCMLAEKIUFPT-UHFFFAOYSA-N n-(ethoxymethyl)-4-methoxy-6-methyl-1,3,5-triazin-2-amine Chemical compound CCOCNC1=NC(C)=NC(OC)=N1 JUFCMLAEKIUFPT-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 229940042880 natural phospholipid Drugs 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000002888 oleic acid derivatives Chemical class 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 239000010451 perlite Substances 0.000 description 1
- 235000019362 perlite Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001522 polyglycol ester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- HYOJDTOWSCGXBK-UHFFFAOYSA-N sodium;(2-chlorophenyl)sulfonylazanide Chemical compound [Na+].[NH-]S(=O)(=O)C1=CC=CC=C1Cl HYOJDTOWSCGXBK-UHFFFAOYSA-N 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- WZHRJGWXUCLILI-UHFFFAOYSA-N sulfonylcarbamic acid Chemical class OC(=O)N=S(=O)=O WZHRJGWXUCLILI-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D521/00—Heterocyclic compounds containing unspecified hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU90600A HU206024B (en) | 1990-01-31 | 1990-01-31 | Herbicidal compositions comprising substituted sulfonylurea derivatives and optionally antidote, as well as process for producing the active ingredients |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PT96606A true PT96606A (pt) | 1991-10-15 |
Family
ID=10950375
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT96606A PT96606A (pt) | 1990-01-31 | 1991-01-30 | Processo para a preparacao de derivados de sulfonilureia substituidos herbicidamente activos e de composicoes herbicidas que os contem |
Country Status (29)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4121185B2 (ja) | 1998-06-12 | 2008-07-23 | 新電元工業株式会社 | 電子回路装置 |
| DE10218704B4 (de) * | 2002-04-26 | 2006-11-30 | Bayer Cropscience Gmbh | Halosulfonylbenzoesäurehalogenide, Verfahren zu deren Herstellung und deren Verwendung zur Herstellung von substituierten Phenylsulfonylharnstoffen |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4371391A (en) * | 1980-09-15 | 1983-02-01 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| US4343649A (en) * | 1980-11-17 | 1982-08-10 | E. I. Du Pont De Nemours And Company | Herbicide antidotes |
| US4545811A (en) * | 1981-08-06 | 1985-10-08 | Ciba-Geigy Corporation | N-Phenylsulfonyl-N'-triazinyl-ureas |
| US4579584A (en) * | 1981-10-13 | 1986-04-01 | Ciba-Geigy Corporation | N-phenylsulfonyl-N'-triazinylureas |
| MA19680A1 (fr) * | 1982-01-11 | 1983-10-01 | Novartis Ag | N- arylsulfonyl - n' - pyrimidinylurees. |
| JPS58126872A (ja) * | 1982-01-22 | 1983-07-28 | Nippon Tokushu Noyaku Seizo Kk | 置換フエニルスルホニルウレア誘導体、その製法及び除草剤 |
| EP0098569A3 (de) * | 1982-07-08 | 1984-12-19 | Hoechst Aktiengesellschaft | Neue heterocyclisch substituierte Sulfonylharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung in der Landwirtschaft |
| BR8304878A (pt) * | 1982-09-10 | 1984-04-24 | Du Pont | Composto e processo para sua preparacao:composicao adequada e processo para controlar o crescimento de vegetacao indesejada |
| DE3481031D1 (de) * | 1983-04-12 | 1990-02-22 | Ciba Geigy Ag | Herbizides mittel. |
| EP0147365A3 (de) * | 1983-11-03 | 1985-10-09 | Ciba-Geigy Ag | Herbizides Mittel |
| US4685961A (en) * | 1984-02-14 | 1987-08-11 | Ciba-Geigy Corporation | Herbicidal sulfonylureas |
| DE3420769A1 (de) * | 1984-06-04 | 1985-12-05 | Bayer Ag, 5090 Leverkusen | Substituierte phenylsulfonylharnstoffe |
| US4645527A (en) * | 1984-12-14 | 1987-02-24 | E. I. Du Pont De Nemours And Company | Herbicidal antidotes |
| EP0190105A3 (de) * | 1985-01-31 | 1988-10-26 | Ciba-Geigy Ag | Herbizides Mittel |
| HU201445B (en) * | 1987-05-28 | 1990-11-28 | Eszakmagyar Vegyimuevek | Herbicide composition containing sulfonyl-urea derivative as active component and glycinamide derivative as antidotum |
-
1990
- 1990-01-31 HU HU90600A patent/HU206024B/hu not_active IP Right Cessation
-
1991
- 1991-01-25 ZA ZA91583A patent/ZA91583B/xx unknown
- 1991-01-28 YU YU36391A patent/YU36391A/sh unknown
- 1991-01-28 CS CS91188A patent/CS18891A2/cs unknown
- 1991-01-29 NO NO91910327A patent/NO910327L/no unknown
- 1991-01-29 GR GR910100041A patent/GR910100041A/el unknown
- 1991-01-29 GB GB9101825A patent/GB2241699A/en not_active Withdrawn
- 1991-01-30 BR BR919100399A patent/BR9100399A/pt unknown
- 1991-01-30 IE IE032191A patent/IE910321A1/en unknown
- 1991-01-30 BE BE9100088A patent/BE1005348A3/fr not_active IP Right Cessation
- 1991-01-30 DK DK016091A patent/DK16091A/da not_active Application Discontinuation
- 1991-01-30 AU AU70082/91A patent/AU638533B2/en not_active Ceased
- 1991-01-30 PT PT96606A patent/PT96606A/pt not_active Application Discontinuation
- 1991-01-30 CA CA002035319A patent/CA2035319A1/en not_active Abandoned
- 1991-01-30 IT ITTO910059A patent/IT1245018B/it active IP Right Grant
- 1991-01-30 SE SE9100289A patent/SE9100289L/xx not_active Application Discontinuation
- 1991-01-31 DE DE4102905A patent/DE4102905A1/de not_active Withdrawn
- 1991-01-31 FR FR9101082A patent/FR2658193A1/fr active Pending
- 1991-01-31 IN IN66/MAS/91A patent/IN171736B/en unknown
- 1991-01-31 JP JP3098310A patent/JPH069577A/ja active Pending
- 1991-01-31 LU LU87884A patent/LU87884A1/de unknown
- 1991-01-31 NL NL9100166A patent/NL9100166A/nl unknown
- 1991-01-31 NZ NZ236977A patent/NZ236977A/en unknown
- 1991-01-31 CN CN91100563A patent/CN1053786A/zh active Pending
- 1991-01-31 FI FI910456A patent/FI910456A7/fi not_active Application Discontinuation
- 1991-01-31 KR KR1019910001821A patent/KR950013855B1/ko not_active Expired - Lifetime
- 1991-01-31 PL PL91293799A patent/PL293799A1/xx unknown
- 1991-01-31 ES ES9100250A patent/ES2033200B1/es not_active Expired - Fee Related
- 1991-01-31 PL PL91288905A patent/PL288905A1/xx unknown
- 1991-02-22 IL IL9197342A patent/IL97342A0/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BB1A | Laying open of patent application |
Effective date: 19910618 |
|
| FC3A | Refusal |
Effective date: 19970507 |