HU190668B - Herbicide compositions containing sulfonyl-urea- or sulfonyl-isourea- derivatives as active agents and process for producing the active agents - Google Patents
Herbicide compositions containing sulfonyl-urea- or sulfonyl-isourea- derivatives as active agents and process for producing the active agents Download PDFInfo
- Publication number
- HU190668B HU190668B HU801806A HU180680A HU190668B HU 190668 B HU190668 B HU 190668B HU 801806 A HU801806 A HU 801806A HU 180680 A HU180680 A HU 180680A HU 190668 B HU190668 B HU 190668B
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- HU
- Hungary
- Prior art keywords
- methyl
- hydrogen
- cwhen
- formula
- methoxy
- Prior art date
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- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 8
- 239000000203 mixture Substances 0.000 title claims description 66
- 238000000034 method Methods 0.000 title claims description 12
- 230000008569 process Effects 0.000 title claims description 5
- 239000013543 active substance Substances 0.000 title claims description 4
- 239000004009 herbicide Substances 0.000 title description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 465
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 84
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 41
- 238000002360 preparation method Methods 0.000 claims abstract description 24
- 150000002540 isothiocyanates Chemical class 0.000 claims abstract description 6
- 229940100389 Sulfonylurea Drugs 0.000 claims abstract description 5
- -1 methoxy, ethoxy Chemical group 0.000 claims description 120
- 229910052739 hydrogen Inorganic materials 0.000 claims description 96
- 239000001257 hydrogen Substances 0.000 claims description 94
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 69
- 229910052757 nitrogen Inorganic materials 0.000 claims description 63
- 239000004480 active ingredient Substances 0.000 claims description 35
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 33
- 239000000460 chlorine Substances 0.000 claims description 33
- 229910052801 chlorine Inorganic materials 0.000 claims description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 26
- 239000007787 solid Substances 0.000 claims description 24
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 24
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 22
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 15
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 15
- 229910052794 bromium Inorganic materials 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- 239000007788 liquid Substances 0.000 claims description 14
- 229910052717 sulfur Chemical group 0.000 claims description 14
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 239000011593 sulfur Chemical group 0.000 claims description 13
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 12
- 239000011737 fluorine Chemical group 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 11
- 125000001246 bromo group Chemical group Br* 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 239000004094 surface-active agent Substances 0.000 claims description 11
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 239000003085 diluting agent Substances 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 238000009472 formulation Methods 0.000 claims description 8
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 7
- 206010029897 Obsessive thoughts Diseases 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- 229960000892 attapulgite Drugs 0.000 claims description 6
- 150000001805 chlorine compounds Chemical class 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 229910052625 palygorskite Inorganic materials 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 4
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims description 4
- RKZXQQPEDGMHBJ-LIGJGSPWSA-N [(2s,3r,4r,5r)-2,3,4,5,6-pentakis[[(z)-octadec-9-enoyl]oxy]hexyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC RKZXQQPEDGMHBJ-LIGJGSPWSA-N 0.000 claims description 4
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims description 4
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims description 3
- 229940077388 benzenesulfonate Drugs 0.000 claims description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- 229910052721 tungsten Inorganic materials 0.000 claims description 2
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 claims 43
- 239000004476 plant protection product Substances 0.000 claims 23
- ASLVVDVJYDCLPC-UHFFFAOYSA-N 2-sulfamoylbenzenesulfonic acid Chemical compound NS(=O)(=O)C1=CC=CC=C1S(O)(=O)=O ASLVVDVJYDCLPC-UHFFFAOYSA-N 0.000 claims 2
- UJPMYEOUBPIPHQ-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical compound CC(F)(F)F UJPMYEOUBPIPHQ-UHFFFAOYSA-N 0.000 claims 1
- RGTVXXNMOGHRAY-WDSKDSINSA-N Cys-Arg Chemical compound SC[C@H](N)C(=O)N[C@H](C(O)=O)CCCN=C(N)N RGTVXXNMOGHRAY-WDSKDSINSA-N 0.000 claims 1
- IMIDOCRTMDIQIJ-UHFFFAOYSA-N aminocarb Chemical compound CNC(=O)OC1=CC=C(N(C)C)C(C)=C1 IMIDOCRTMDIQIJ-UHFFFAOYSA-N 0.000 claims 1
- VJDZMZAZDFKMSV-UHFFFAOYSA-N benzene-1,2-disulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1S(N)(=O)=O VJDZMZAZDFKMSV-UHFFFAOYSA-N 0.000 claims 1
- WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 1
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims 1
- 239000000575 pesticide Substances 0.000 claims 1
- 239000011814 protection agent Substances 0.000 claims 1
- 239000003223 protective agent Substances 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 150000003456 sulfonamides Chemical class 0.000 abstract description 23
- 229940124530 sulfonamide Drugs 0.000 abstract description 17
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract description 13
- 239000012948 isocyanate Substances 0.000 abstract description 12
- 150000002513 isocyanates Chemical class 0.000 abstract description 7
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 abstract description 6
- 229910052736 halogen Inorganic materials 0.000 abstract description 4
- 150000002367 halogens Chemical class 0.000 abstract description 4
- 239000000543 intermediate Substances 0.000 abstract description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 abstract description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 abstract 1
- 125000004438 haloalkoxy group Chemical group 0.000 abstract 1
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 abstract 1
- CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 abstract 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
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- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 1
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- 230000002378 acidificating effect Effects 0.000 description 1
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- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
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- 238000005576 amination reaction Methods 0.000 description 1
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- UYJXRRSPUVSSMN-UHFFFAOYSA-P ammonium sulfide Chemical compound [NH4+].[NH4+].[S-2] UYJXRRSPUVSSMN-UHFFFAOYSA-P 0.000 description 1
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- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
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- OTKPPUXRIADSGD-PPRNARJGSA-N avoparcina Chemical compound O([C@@H]1C2=CC=C(C(=C2)Cl)OC=2C=C3C=C(C=2O[C@H]2C([C@@H](O)[C@H](O)[C@@H](CO)O2)O[C@@H]2O[C@@H](C)[C@H](O)[C@H](N)C2)OC2=CC=C(C=C2)[C@@H](O)[C@H](C(N[C@H](C(=O)N[C@H]3C(=O)N[C@H]2C(=O)N[C@@H]1C(N[C@@H](C1=CC(O)=CC(O)=C1C=1C(O)=CC=C2C=1)C(O)=O)=O)C=1C=CC(O)=CC=1)=O)NC(=O)[C@H](NC)C=1C=CC(O[C@H]2[C@@H]([C@H](O)[C@@H](O)[C@H](C)O2)O)=CC=1)[C@H]1C[C@@H](N)[C@@H](O)[C@H](C)O1 OTKPPUXRIADSGD-PPRNARJGSA-N 0.000 description 1
- MCOQHIWZJUDQIC-UHFFFAOYSA-N barban Chemical compound ClCC#CCOC(=O)NC1=CC=CC(Cl)=C1 MCOQHIWZJUDQIC-UHFFFAOYSA-N 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
- 150000008331 benzenesulfonamides Chemical class 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
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- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 1
- BFXLJWUGRPGMFU-UHFFFAOYSA-N dipropoxyphosphinothioyl n,n-diethylcarbamodithioate;sulfane Chemical compound S.CCCOP(=S)(OCCC)SC(=S)N(CC)CC BFXLJWUGRPGMFU-UHFFFAOYSA-N 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
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- 239000007789 gas Substances 0.000 description 1
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 1
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- 208000006278 hypochromic anemia Diseases 0.000 description 1
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- 239000011777 magnesium Substances 0.000 description 1
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- 238000001819 mass spectrum Methods 0.000 description 1
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- 239000002184 metal Substances 0.000 description 1
- BACHBFVBHLGWSL-UHFFFAOYSA-N methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate Chemical compound C1=CC(OC(C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-UHFFFAOYSA-N 0.000 description 1
- UNSXBLRNWSMFQQ-UHFFFAOYSA-N methyl n'-[2-(diethylsulfamoyl)phenyl]sulfonyl-n-(4,6-dimethoxy-1,3,5-triazin-2-yl)carbamimidothioate Chemical compound CCN(CC)S(=O)(=O)C1=CC=CC=C1S(=O)(=O)\N=C(SC)\NC1=NC(OC)=NC(OC)=N1 UNSXBLRNWSMFQQ-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
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- 230000003020 moisturizing 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
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- IHYNKGRWCDKNEG-UHFFFAOYSA-N n-(4-bromophenyl)-2,6-dihydroxybenzamide Chemical compound OC1=CC=CC(O)=C1C(=O)NC1=CC=C(Br)C=C1 IHYNKGRWCDKNEG-UHFFFAOYSA-N 0.000 description 1
- FJYDLHMQVPRHCF-UHFFFAOYSA-N n-(oxomethylidene)-2-(2,2,2-trifluoroethylsulfonyl)benzenesulfonamide Chemical compound FC(F)(F)CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)N=C=O FJYDLHMQVPRHCF-UHFFFAOYSA-N 0.000 description 1
- BXXCVLBQEGJZLG-UHFFFAOYSA-N n-methyl-2-nitro-n-phenylmethoxybenzenesulfonamide Chemical compound C=1C=CC=C([N+]([O-])=O)C=1S(=O)(=O)N(C)OCC1=CC=CC=C1 BXXCVLBQEGJZLG-UHFFFAOYSA-N 0.000 description 1
- DLJPYODODWSDBI-UHFFFAOYSA-N n-methyl-2-nitrobenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC=C1[N+]([O-])=O DLJPYODODWSDBI-UHFFFAOYSA-N 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 235000020030 perry Nutrition 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 230000019612 pigmentation Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000011591 potassium Chemical group 0.000 description 1
- 229910052700 potassium Chemical group 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
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- 239000002516 radical scavenger Substances 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229910002029 synthetic silica gel Inorganic materials 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 210000002435 tendon Anatomy 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/65—N-sulfonylisocyanates
-
- 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
- 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
- A01N47/40—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides
- A01N47/42—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- 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
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines having three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D521/00—Heterocyclic compounds containing unspecified hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5915379A | 1979-07-20 | 1979-07-20 | |
| US13034280A | 1980-03-14 | 1980-03-14 | |
| US06/152,022 US4310346A (en) | 1980-03-14 | 1980-05-30 | N(Substituted phenylsulfonyl) N'(substituted cyumidin-2-yl) ureas |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU190668B true HU190668B (en) | 1986-10-28 |
Family
ID=27369593
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU801806A HU190668B (en) | 1979-07-20 | 1980-07-18 | Herbicide compositions containing sulfonyl-urea- or sulfonyl-isourea- derivatives as active agents and process for producing the active agents |
Country Status (16)
| Country | Link |
|---|---|
| EP (2) | EP0070041A3 (OSRAM) |
| AU (2) | AU536787B2 (OSRAM) |
| BR (1) | BR8004382A (OSRAM) |
| CA (1) | CA1144923A (OSRAM) |
| DE (1) | DE3067433D1 (OSRAM) |
| DK (1) | DK259280A (OSRAM) |
| ES (1) | ES8105274A1 (OSRAM) |
| GB (1) | GB2057429B (OSRAM) |
| GR (1) | GR69301B (OSRAM) |
| HU (1) | HU190668B (OSRAM) |
| IE (1) | IE50022B1 (OSRAM) |
| IL (1) | IL60631A (OSRAM) |
| NZ (1) | NZ194385A (OSRAM) |
| PH (1) | PH16406A (OSRAM) |
| PT (1) | PT71580B (OSRAM) |
| TR (1) | TR21772A (OSRAM) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4443243A (en) * | 1981-07-16 | 1984-04-17 | Ciba-Geigy Corporation | N-Phenylsulfonyl-N-triazinylureas |
| DE3466986D1 (de) * | 1983-02-04 | 1987-12-03 | Ciba Geigy Ag | N-phenylsulfonyl-n'-pyrimidinyl- and -triazinylurea |
| EP0126711B1 (de) * | 1983-05-16 | 1989-08-02 | Ciba-Geigy Ag | Herbizid wirksame und pflanzenwuchsregulierende Pyrimidin-Derivate, deren Herstellung und Verwendung |
| AU575335B2 (en) * | 1983-08-05 | 1988-07-28 | E.I. Du Pont De Nemours And Company | Benzene sulfonamides |
| JPS60146878A (ja) * | 1984-01-10 | 1985-08-02 | Nippon Tokushu Noyaku Seizo Kk | スルホニルグアニジン誘導体，その製法及び除草剤 |
| JPS60166668A (ja) * | 1984-02-10 | 1985-08-29 | Nippon Tokushu Noyaku Seizo Kk | ２−アルコキシアミノスルホニルベンゼン−スルホニルウレア誘導体、その製法及び除草剤 |
| AU585761B2 (en) * | 1984-03-07 | 1989-06-22 | E.I. Du Pont De Nemours And Company | Herbicidal fluoroethoxy triazines |
| EP0158600B1 (de) * | 1984-04-11 | 1991-04-03 | Ciba-Geigy Ag | Verfahren zur selektiven Unkrautbekämpfung in Nutzpflanzenkulturen |
| DE3516616A1 (de) * | 1984-08-30 | 1986-03-13 | Bayer Ag, 5090 Leverkusen | Benzodisultame |
| CA1226862A (en) * | 1985-02-21 | 1987-09-15 | Donald J. Dumas | Herbicidal sulfonamides |
| US4678498A (en) * | 1985-06-12 | 1987-07-07 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| GB8719730D0 (en) * | 1987-08-20 | 1987-09-30 | Vickers Plc | Radiation sensitive compounds |
| DE4439675A1 (de) * | 1994-11-07 | 1996-05-09 | Hoechst Schering Agrevo Gmbh | N-Acyl-N-alkylaminophenylsulfonylharnstoffe mit Schwefelsubstituenten, Verfahren zur Herstellung und Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
| DE4439676A1 (de) * | 1994-11-07 | 1996-05-09 | Hoechst Schering Agrevo Gmbh | Schwefelsubstituierte Phenylsulfonylharnstoffe, Verfahren zu deren Herstellung und Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
| ZA974703B (en) * | 1996-05-30 | 1997-12-30 | Bayer Ag | Substituted sulfonylamino(thio)carbonyl compounds. |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| OA05625A (fr) * | 1976-04-07 | 1981-04-30 | Du Pont | N-(hétérocyclique aminocarbonyl) aryl sulfonamides herbicides, compositions les contenant et procédés les utilisant . |
| US4257802A (en) * | 1977-10-06 | 1981-03-24 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| DK168779A (da) * | 1978-05-30 | 1979-12-01 | Du Pont | Agrikulturelle carbaminidothioater |
-
1980
- 1980-06-17 DK DK259280A patent/DK259280A/da not_active Application Discontinuation
- 1980-07-15 BR BR8004382A patent/BR8004382A/pt unknown
- 1980-07-15 CA CA000356200A patent/CA1144923A/en not_active Expired
- 1980-07-18 HU HU801806A patent/HU190668B/hu unknown
- 1980-07-18 PT PT71580A patent/PT71580B/pt unknown
- 1980-07-18 AU AU60601/80A patent/AU536787B2/en not_active Ceased
- 1980-07-18 PH PH24308A patent/PH16406A/en unknown
- 1980-07-18 EP EP82107279A patent/EP0070041A3/en not_active Withdrawn
- 1980-07-18 DE DE8080302433T patent/DE3067433D1/de not_active Expired
- 1980-07-18 IL IL60631A patent/IL60631A/xx unknown
- 1980-07-18 IE IE1495/80A patent/IE50022B1/en unknown
- 1980-07-18 GB GB8023622A patent/GB2057429B/en not_active Expired
- 1980-07-18 EP EP80302433A patent/EP0023141B1/en not_active Expired
- 1980-07-18 NZ NZ194385A patent/NZ194385A/xx unknown
- 1980-07-18 TR TR21772A patent/TR21772A/xx unknown
- 1980-07-18 ES ES493524A patent/ES8105274A1/es not_active Expired
- 1980-07-19 GR GR62499A patent/GR69301B/el unknown
-
1984
- 1984-02-23 AU AU24898/84A patent/AU2489884A/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP0023141B1 (en) | 1984-04-11 |
| CA1144923A (en) | 1983-04-19 |
| GB2057429B (en) | 1983-07-20 |
| EP0023141A2 (en) | 1981-01-28 |
| GR69301B (OSRAM) | 1982-05-14 |
| AU536787B2 (en) | 1984-05-24 |
| PH16406A (en) | 1983-09-26 |
| TR21772A (tr) | 1985-07-01 |
| EP0023141A3 (en) | 1981-04-01 |
| PT71580B (en) | 1982-02-19 |
| BR8004382A (pt) | 1981-02-24 |
| PT71580A (en) | 1980-08-01 |
| IL60631A0 (en) | 1980-09-16 |
| DK259280A (da) | 1981-01-21 |
| EP0070041A3 (en) | 1983-04-13 |
| AU6060180A (en) | 1981-01-22 |
| GB2057429A (en) | 1981-04-01 |
| EP0070041A2 (en) | 1983-01-19 |
| IE801495L (en) | 1981-01-20 |
| IE50022B1 (en) | 1986-02-05 |
| NZ194385A (en) | 1982-12-07 |
| IL60631A (en) | 1986-03-31 |
| ES493524A0 (es) | 1981-06-01 |
| DE3067433D1 (en) | 1984-05-17 |
| ES8105274A1 (es) | 1981-06-01 |
| AU2489884A (en) | 1984-07-05 |
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