CA1232269A - 1,2,4-triazole¬1,5-a|pyrimidine-2-sulfonamides substitues et composes et methodes pour lutter contre les mauvaises herbes et empecher la nitrification de l'azote ammoniacal dans le sol - Google Patents

1,2,4-triazole¬1,5-a|pyrimidine-2-sulfonamides substitues et composes et methodes pour lutter contre les mauvaises herbes et empecher la nitrification de l'azote ammoniacal dans le sol

Info

Publication number: CA1232269A
Authority: CA; Canada
Prior art keywords: methyl; pyrimidine; triazolo; sulfonyl; owe
Prior art date: 1983-11-14
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.): Expired

Application number

CA000527878A

Other languages

English (en)

Inventor

Norman R. Pearson

William A. Kleschick

Richard W. Meikle

Mark J. Costales

William T. Monte

Robert J Ehr

Ben C. Gerwick, Iii

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Dow Chemical Co

Original Assignee

Dow Chemical Co

Priority date (The priority date 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 date listed.)

1983-11-14

Filing date

1987-01-21

Publication date

1988-02-02

1984-11-13 Priority claimed from CA000467616A external-priority patent/CA1231708A/fr

1987-01-21 Application filed by Dow Chemical Co filed Critical Dow Chemical Co

1987-01-21 Priority to CA000527878A priority Critical patent/CA1232269A/fr

1988-02-02 Application granted granted Critical

1988-02-02 Publication of CA1232269A publication Critical patent/CA1232269A/fr

Status Expired legal-status Critical Current

Links

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229910052739 hydrogen Inorganic materials 0.000 claims abstract description 38
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SRNKZYRMFBGSGE-UHFFFAOYSA-N [1,2,4]triazolo[1,5-a]pyrimidine Chemical class N1=CC=CN2N=CN=C21 SRNKZYRMFBGSGE-UHFFFAOYSA-N 0.000 abstract description 2
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MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
PDQRIMRBJSQRSL-UHFFFAOYSA-N di(propan-2-yl)carbamothioic s-acid Chemical compound CC(C)N(C(C)C)C(S)=O PDQRIMRBJSQRSL-UHFFFAOYSA-N 0.000 description 1
125000004472 dialkylaminosulfonyl group Chemical group 0.000 description 1
229910000388 diammonium phosphate Inorganic materials 0.000 description 1
NZZIMKJIVMHWJC-UHFFFAOYSA-N dibenzoylmethane Chemical compound C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 description 1
RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
239000002283 diesel fuel Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
LRBPFPZTIZSOGG-UHFFFAOYSA-N dimethyl 2-methylpropanedioate Chemical compound COC(=O)C(C)C(=O)OC LRBPFPZTIZSOGG-UHFFFAOYSA-N 0.000 description 1
BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 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
RZMWTGFSAMRLQH-UHFFFAOYSA-L disodium;2,2-dihexyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCC RZMWTGFSAMRLQH-UHFFFAOYSA-L 0.000 description 1
238000004821 distillation Methods 0.000 description 1
ODCCJTMPMUFERV-UHFFFAOYSA-N ditert-butyl carbonate Chemical compound CC(C)(C)OC(=O)OC(C)(C)C ODCCJTMPMUFERV-UHFFFAOYSA-N 0.000 description 1
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000000428 dust Substances 0.000 description 1
238000010410 dusting Methods 0.000 description 1
150000002084 enol ethers Chemical class 0.000 description 1
150000002085 enols Chemical group 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
239000004210 ether based solvent Substances 0.000 description 1
VBIMAPYCCBGZMD-UHFFFAOYSA-N ethyl 2-[(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)sulfonylamino]-3-(trifluoromethyl)benzoate Chemical compound CCOC(=O)C1=CC=CC(C(F)(F)F)=C1NS(=O)(=O)C1=NN2C=CC(C)=NC2=N1 VBIMAPYCCBGZMD-UHFFFAOYSA-N 0.000 description 1
GKFONISULMGIJK-UHFFFAOYSA-N ethyl 2-benzylsulfanyl-7-methyl-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate Chemical compound N=1N2C(C)=C(C(=O)OCC)C=NC2=NC=1SCC1=CC=CC=C1 GKFONISULMGIJK-UHFFFAOYSA-N 0.000 description 1
ZTXQGDFNJJSAQP-UHFFFAOYSA-N ethyl 2-chlorosulfonyl-7-methyl-[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate Chemical compound CC1=C(C(=O)OCC)C=NC2=NC(S(Cl)(=O)=O)=NN21 ZTXQGDFNJJSAQP-UHFFFAOYSA-N 0.000 description 1
JHZPNBKZPAWCJD-UHFFFAOYSA-N ethyl 2-oxocyclopentane-1-carboxylate Chemical compound CCOC(=O)C1CCCC1=O JHZPNBKZPAWCJD-UHFFFAOYSA-N 0.000 description 1
QGIRUMFKKJUEAN-UHFFFAOYSA-N ethyl 3,4-dimethyl-2-[(7-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)sulfonylamino]benzoate Chemical compound CCOC(=O)C1=CC=C(C)C(C)=C1NS(=O)(=O)C1=NN2C(C)=CC=NC2=N1 QGIRUMFKKJUEAN-UHFFFAOYSA-N 0.000 description 1
SBDGTUVBAHVKEA-UHFFFAOYSA-N ethyl 3-chloro-2-[(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)sulfonylamino]benzoate Chemical compound CCOC(=O)C1=CC=CC(Cl)=C1NS(=O)(=O)C1=NN2C(C)=CC(C)=NC2=N1 SBDGTUVBAHVKEA-UHFFFAOYSA-N 0.000 description 1
FGHMIWPYUOCIEU-UHFFFAOYSA-N ethyl 3-fluoro-2-[(6-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)sulfonylamino]benzoate Chemical compound CCOC(=O)C1=CC=CC(F)=C1NS(=O)(=O)C1=NN2C=C(C)C=NC2=N1 FGHMIWPYUOCIEU-UHFFFAOYSA-N 0.000 description 1
QWOCMRCMTRZZBS-UHFFFAOYSA-N ethyl 3-methyl-2-[(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)sulfonylamino]benzoate Chemical compound CCOC(=O)C1=CC=CC(C)=C1NS(=O)(=O)C1=NN2C=CC(C)=NC2=N1 QWOCMRCMTRZZBS-UHFFFAOYSA-N 0.000 description 1
KAJPFWOJMWDBIM-UHFFFAOYSA-N ethyl 3-methyl-2-[(7-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)sulfonylamino]benzoate Chemical compound CCOC(=O)C1=CC=CC(C)=C1NS(=O)(=O)C1=NN2C(C)=CC=NC2=N1 KAJPFWOJMWDBIM-UHFFFAOYSA-N 0.000 description 1
ZOBDLEVQBHRGBL-UHFFFAOYSA-N ethyl 4-chloro-3-methyl-2-[(6-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)sulfonylamino]benzoate Chemical compound CCOC(=O)C1=CC=C(Cl)C(C)=C1NS(=O)(=O)C1=NN2C=C(C)C=NC2=N1 ZOBDLEVQBHRGBL-UHFFFAOYSA-N 0.000 description 1
XDHWYQRLMSOZOP-UHFFFAOYSA-N ethyl 5-ethoxy-3-oxopent-4-enoate Chemical compound CCOC=CC(=O)CC(=O)OCC XDHWYQRLMSOZOP-UHFFFAOYSA-N 0.000 description 1
JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
RZILCCPWPBTYDO-UHFFFAOYSA-N fluometuron Chemical compound CN(C)C(=O)NC1=CC=CC(C(F)(F)F)=C1 RZILCCPWPBTYDO-UHFFFAOYSA-N 0.000 description 1
239000012634 fragment Substances 0.000 description 1
239000000295 fuel oil Substances 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
230000008570 general process Effects 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000003292 glue Substances 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 1
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
229910052737 gold Inorganic materials 0.000 description 1
239000010931 gold Substances 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
125000004692 haloalkylcarbonyl group Chemical group 0.000 description 1
150000002366 halogen compounds Chemical group 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
QAMFBRUWYYMMGJ-UHFFFAOYSA-N hexafluoroacetylacetone Chemical compound FC(F)(F)C(=O)CC(=O)C(F)(F)F QAMFBRUWYYMMGJ-UHFFFAOYSA-N 0.000 description 1
229940088597 hormone Drugs 0.000 description 1
239000005556 hormone Substances 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
230000003993 interaction Effects 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
239000003621 irrigation water Substances 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
239000010410 layer Substances 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
239000004571 lime Substances 0.000 description 1
239000012035 limiting reagent Substances 0.000 description 1
235000014666 liquid concentrate Nutrition 0.000 description 1
DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000005358 mercaptoalkyl group Chemical group 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
AWIJRPNMLHPLNC-UHFFFAOYSA-N methanethioic s-acid Chemical class SC=O AWIJRPNMLHPLNC-UHFFFAOYSA-N 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
MBIYSZXWCHDXFQ-UHFFFAOYSA-N methyl 2-[(6-chloro-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)sulfonylamino]-3-methylbenzoate Chemical compound COC(=O)C1=CC=CC(C)=C1NS(=O)(=O)C1=NN2C=C(Cl)C=NC2=N1 MBIYSZXWCHDXFQ-UHFFFAOYSA-N 0.000 description 1
WYJPYXQXMGODTR-UHFFFAOYSA-N methyl 2-[(6-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)sulfonylamino]-3-(trifluoromethyl)benzoate Chemical compound COC(=O)C1=CC=CC(C(F)(F)F)=C1NS(=O)(=O)C1=NN2C=C(C)C=NC2=N1 WYJPYXQXMGODTR-UHFFFAOYSA-N 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
MSXSZFYRADEEJA-UHFFFAOYSA-N methyl 2-amino-3-chlorobenzoate Chemical compound COC(=O)C1=CC=CC(Cl)=C1N MSXSZFYRADEEJA-UHFFFAOYSA-N 0.000 description 1
SXQHVYMOFKXKPG-UHFFFAOYSA-N methyl 2-amino-4-chloro-3-methylbenzoate Chemical compound COC(=O)C1=CC=C(Cl)C(C)=C1N SXQHVYMOFKXKPG-UHFFFAOYSA-N 0.000 description 1
IDHGNWHVRRKTEK-UHFFFAOYSA-N methyl 3,4-dimethyl-2-[(6-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)sulfonylamino]benzoate Chemical compound COC(=O)C1=CC=C(C)C(C)=C1NS(=O)(=O)C1=NN2C=C(C)C=NC2=N1 IDHGNWHVRRKTEK-UHFFFAOYSA-N 0.000 description 1
YPEMWWHAEVJGIS-UHFFFAOYSA-N methyl 3-amino-2,4-dichlorobenzoate Chemical compound COC(=O)C1=CC=C(Cl)C(N)=C1Cl YPEMWWHAEVJGIS-UHFFFAOYSA-N 0.000 description 1
YLKYUQIJIVDUAP-UHFFFAOYSA-N methyl 3-amino-2-bromo-4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C(N)=C1Br YLKYUQIJIVDUAP-UHFFFAOYSA-N 0.000 description 1
YFQITNUODSHJBJ-UHFFFAOYSA-N methyl 3-chloro-2-[(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)sulfonylamino]benzoate Chemical compound COC(=O)C1=CC=CC(Cl)=C1NS(=O)(=O)C1=NN2C=CC(C)=NC2=N1 YFQITNUODSHJBJ-UHFFFAOYSA-N 0.000 description 1
KYSCBBAGAOWBDD-UHFFFAOYSA-N methyl 3-chloro-2-[(7-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)sulfonylamino]benzoate Chemical compound COC(=O)C1=CC=CC(Cl)=C1NS(=O)(=O)C1=NN2C(C)=CC=NC2=N1 KYSCBBAGAOWBDD-UHFFFAOYSA-N 0.000 description 1
XPSCZRUYGVKBQI-UHFFFAOYSA-N methyl 3-fluoro-2-[(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)sulfonylamino]benzoate Chemical compound COC(=O)C1=CC=CC(F)=C1NS(=O)(=O)C1=NN2C=CC(C)=NC2=N1 XPSCZRUYGVKBQI-UHFFFAOYSA-N 0.000 description 1
KCZCSLQLQMBWLE-UHFFFAOYSA-N methyl 3-fluoro-2-[(7-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)sulfonylamino]benzoate Chemical compound COC(=O)C1=CC=CC(F)=C1NS(=O)(=O)C1=NN2C(C)=CC=NC2=N1 KCZCSLQLQMBWLE-UHFFFAOYSA-N 0.000 description 1
SSMRXJOGRTYEIB-UHFFFAOYSA-N methyl 3-methyl-2-[(6-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)sulfonylamino]benzoate Chemical compound COC(=O)C1=CC=CC(C)=C1NS(=O)(=O)C1=NN2C=C(C)C=NC2=N1 SSMRXJOGRTYEIB-UHFFFAOYSA-N 0.000 description 1
CLJNWSLEVSJEIJ-UHFFFAOYSA-N methyl 4-chloro-3-methyl-2-[(6-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)sulfonylamino]benzoate Chemical compound COC(=O)C1=CC=C(Cl)C(C)=C1NS(=O)(=O)C1=NN2C=C(C)C=NC2=N1 CLJNWSLEVSJEIJ-UHFFFAOYSA-N 0.000 description 1
229940102398 methyl anthranilate Drugs 0.000 description 1
229940095102 methyl benzoate Drugs 0.000 description 1
DDCYYCUMAFYDDU-UHFFFAOYSA-N methyl thiohypochlorite Chemical compound CSCl DDCYYCUMAFYDDU-UHFFFAOYSA-N 0.000 description 1
XBCXJKGHPABGSD-UHFFFAOYSA-N methyluracil Natural products CN1C=CC(=O)NC1=O XBCXJKGHPABGSD-UHFFFAOYSA-N 0.000 description 1
FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 description 1
244000005700 microbiome Species 0.000 description 1
XBMFYHVVXRCKLE-UHFFFAOYSA-N n-(2,3-dichloro-6-methylphenyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide Chemical compound CC1=CC=C(Cl)C(Cl)=C1NS(=O)(=O)C1=NN2C(C)=CC=NC2=N1 XBMFYHVVXRCKLE-UHFFFAOYSA-N 0.000 description 1
LKMONOAQBJCDAU-UHFFFAOYSA-N n-(2,3-dimethyl-6-nitrophenyl)-5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide Chemical compound N1=C2N=C(C)C=C(C)N2N=C1S(=O)(=O)NC1=C(C)C(C)=CC=C1[N+]([O-])=O LKMONOAQBJCDAU-UHFFFAOYSA-N 0.000 description 1
SSHJVILOSQYMEE-UHFFFAOYSA-N n-(2,3-dimethyl-6-nitrophenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide Chemical compound N1=C2N=C(C)C=CN2N=C1S(=O)(=O)NC1=C(C)C(C)=CC=C1[N+]([O-])=O SSHJVILOSQYMEE-UHFFFAOYSA-N 0.000 description 1
HCOWTGGHXWBBMP-UHFFFAOYSA-N n-(2,3-dimethyl-6-nitrophenyl)-6-methyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide Chemical compound N=1N2C=C(C)C=NC2=NC=1S(=O)(=O)NC1=C(C)C(C)=CC=C1[N+]([O-])=O HCOWTGGHXWBBMP-UHFFFAOYSA-N 0.000 description 1
VXZLWFLHPYVOCQ-UHFFFAOYSA-N n-(2,3-dimethyl-6-nitrophenyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide Chemical compound CC1=CC=C([N+]([O-])=O)C(NS(=O)(=O)C2=NN3C(C)=CC=NC3=N2)=C1C VXZLWFLHPYVOCQ-UHFFFAOYSA-N 0.000 description 1
UVSDJGHAQUEHJH-UHFFFAOYSA-N n-(2,6-dichloro-3-methylphenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide Chemical compound N1=C2N=C(C)C=CN2N=C1S(=O)(=O)NC1=C(Cl)C=CC(C)=C1Cl UVSDJGHAQUEHJH-UHFFFAOYSA-N 0.000 description 1
QLCCSEGKAFXPDF-UHFFFAOYSA-N n-(2,6-dichloro-3-methylphenyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide Chemical compound CC1=CC=C(Cl)C(NS(=O)(=O)C2=NN3C(C)=CC=NC3=N2)=C1Cl QLCCSEGKAFXPDF-UHFFFAOYSA-N 0.000 description 1
ZTQFPDJKZWJTKL-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-5-methoxy-[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide Chemical compound N1=C2N=C(OC)C=CN2N=C1S(=O)(=O)NC1=C(Cl)C=CC=C1Cl ZTQFPDJKZWJTKL-UHFFFAOYSA-N 0.000 description 1
DWKKEKNUJWWRQT-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-5-methyl-1,5,6,7-tetrahydro-[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide Chemical compound N=1C2=NC(C)CCN2NC=1S(=O)(=O)NC1=C(Cl)C=CC=C1Cl DWKKEKNUJWWRQT-UHFFFAOYSA-N 0.000 description 1
UCQSKNBNWBEZSA-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-n-[(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)sulfonyl]-2-methylpropanamide Chemical compound N1=C2N=C(C)C=C(C)N2N=C1S(=O)(=O)N(C(=O)C(C)C)C1=C(Cl)C=CC=C1Cl UCQSKNBNWBEZSA-UHFFFAOYSA-N 0.000 description 1
TUDPAYMNMVGVPY-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-n-[(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)sulfonyl]acetamide Chemical compound N1=C2N=C(C)C=C(C)N2N=C1S(=O)(=O)N(C(=O)C)C1=C(Cl)C=CC=C1Cl TUDPAYMNMVGVPY-UHFFFAOYSA-N 0.000 description 1
CSGIALKENNSPAB-UHFFFAOYSA-N n-(2,6-difluoro-3-methylphenyl)-5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide Chemical compound N1=C2N=C(C)C=C(C)N2N=C1S(=O)(=O)NC1=C(F)C=CC(C)=C1F CSGIALKENNSPAB-UHFFFAOYSA-N 0.000 description 1
CUOKYGZANBXFKR-UHFFFAOYSA-N n-(2,6-difluoro-3-methylphenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide Chemical compound N1=C2N=C(C)C=CN2N=C1S(=O)(=O)NC1=C(F)C=CC(C)=C1F CUOKYGZANBXFKR-UHFFFAOYSA-N 0.000 description 1
NASFODCLFWVHMR-UHFFFAOYSA-N n-(2,6-difluorophenyl)-6-methyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide Chemical compound N=1N2C=C(C)C=NC2=NC=1S(=O)(=O)NC1=C(F)C=CC=C1F NASFODCLFWVHMR-UHFFFAOYSA-N 0.000 description 1
WQWQDYNUDSJIBH-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide Chemical compound N1=C2N=C(C)C=C(C)N2N=C1S(=O)(=O)NC1=C(C)C=CC=C1C WQWQDYNUDSJIBH-UHFFFAOYSA-N 0.000 description 1
HRMCLXRQRDSPDM-UHFFFAOYSA-N n-(2-bromo-6-methylphenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide Chemical compound N1=C2N=C(C)C=CN2N=C1S(=O)(=O)NC1=C(C)C=CC=C1Br HRMCLXRQRDSPDM-UHFFFAOYSA-N 0.000 description 1
PTOKRGDNHREHEW-UHFFFAOYSA-N n-(2-bromo-6-methylphenyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide Chemical compound CC1=CC=CC(Br)=C1NS(=O)(=O)C1=NN2C(C)=CC=NC2=N1 PTOKRGDNHREHEW-UHFFFAOYSA-N 0.000 description 1
WWBULYWJPMWXGR-UHFFFAOYSA-N n-(2-chloro-6-phenylphenyl)-5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide Chemical compound N1=C2N=C(C)C=C(C)N2N=C1S(=O)(=O)NC1=C(Cl)C=CC=C1C1=CC=CC=C1 WWBULYWJPMWXGR-UHFFFAOYSA-N 0.000 description 1
CXNZGRPMUSTVQS-UHFFFAOYSA-N n-(2-chloro-6-phenylphenyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide Chemical compound N=1N2C(C)=CC=NC2=NC=1S(=O)(=O)NC1=C(Cl)C=CC=C1C1=CC=CC=C1 CXNZGRPMUSTVQS-UHFFFAOYSA-N 0.000 description 1
DNLFVUOLXYKUSN-UHFFFAOYSA-N n-(2-fluoro-6-methylphenyl)-7-methyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide Chemical compound CC1=CC=CC(F)=C1NS(=O)(=O)C1=NN2C(C)=CC=NC2=N1 DNLFVUOLXYKUSN-UHFFFAOYSA-N 0.000 description 1
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230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
125000005646 oximino group Chemical group 0.000 description 1
VSXGXPNADZQTGQ-UHFFFAOYSA-N oxirane;phenol Chemical compound C1CO1.OC1=CC=CC=C1 VSXGXPNADZQTGQ-UHFFFAOYSA-N 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
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RGCLLPNLLBQHPF-HJWRWDBZSA-N phosphamidon Chemical compound CCN(CC)C(=O)C(\Cl)=C(/C)OP(=O)(OC)OC RGCLLPNLLBQHPF-HJWRWDBZSA-N 0.000 description 1
230000029553 photosynthesis Effects 0.000 description 1
238000010672 photosynthesis Methods 0.000 description 1
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LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
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150000003141 primary amines Chemical class 0.000 description 1
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LNOWBYZFRXLMKE-UHFFFAOYSA-N prop-2-enyl 3-methyl-2-[(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)sulfonylamino]benzoate Chemical compound N1=C2N=C(C)C=CN2N=C1S(=O)(=O)NC1=C(C)C=CC=C1C(=O)OCC=C LNOWBYZFRXLMKE-UHFFFAOYSA-N 0.000 description 1
NSSBZLSJSVGXNZ-UHFFFAOYSA-N prop-2-enyl 3-methyl-2-[(6-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)sulfonylamino]benzoate Chemical compound N=1N2C=C(C)C=NC2=NC=1S(=O)(=O)NC1=C(C)C=CC=C1C(=O)OCC=C NSSBZLSJSVGXNZ-UHFFFAOYSA-N 0.000 description 1
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LVFVNVZQRDKURW-UHFFFAOYSA-N propan-2-yl 3-chloro-2-[(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)sulfonylamino]benzoate Chemical compound CC(C)OC(=O)C1=CC=CC(Cl)=C1NS(=O)(=O)C1=NN2C(C)=CC(C)=NC2=N1 LVFVNVZQRDKURW-UHFFFAOYSA-N 0.000 description 1
CPWXETNJJZFIPT-UHFFFAOYSA-N propan-2-yl 3-chloro-2-[(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)sulfonylamino]benzoate Chemical compound CC(C)OC(=O)C1=CC=CC(Cl)=C1NS(=O)(=O)C1=NN2C=CC(C)=NC2=N1 CPWXETNJJZFIPT-UHFFFAOYSA-N 0.000 description 1
PFBLASRDPXHVQA-UHFFFAOYSA-N propan-2-yl 3-chloro-2-[(7-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)sulfonylamino]benzoate Chemical compound CC(C)OC(=O)C1=CC=CC(Cl)=C1NS(=O)(=O)C1=NN2C(C)=CC=NC2=N1 PFBLASRDPXHVQA-UHFFFAOYSA-N 0.000 description 1
VGHMXRKJEFPKEN-UHFFFAOYSA-N propan-2-yl 3-fluoro-2-[(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)sulfonylamino]benzoate Chemical compound CC(C)OC(=O)C1=CC=CC(F)=C1NS(=O)(=O)C1=NN2C=CC(C)=NC2=N1 VGHMXRKJEFPKEN-UHFFFAOYSA-N 0.000 description 1
HFOMVCLNVYBAQJ-UHFFFAOYSA-N propan-2-yl 3-fluoro-2-[(7-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)sulfonylamino]benzoate Chemical compound CC(C)OC(=O)C1=CC=CC(F)=C1NS(=O)(=O)C1=NN2C(C)=CC=NC2=N1 HFOMVCLNVYBAQJ-UHFFFAOYSA-N 0.000 description 1
RITDHRWNDQZSCY-UHFFFAOYSA-N propan-2-yl 3-methyl-2-[(6-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)sulfonylamino]benzoate Chemical compound CC(C)OC(=O)C1=CC=CC(C)=C1NS(=O)(=O)C1=NN2C=C(C)C=NC2=N1 RITDHRWNDQZSCY-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 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
OXPUNWHFQLHHHF-UHFFFAOYSA-N pyridin-2-ylmethyl 3-methyl-2-[(6-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)sulfonylamino]benzoate Chemical compound N=1N2C=C(C)C=NC2=NC=1S(=O)(=O)NC1=C(C)C=CC=C1C(=O)OCC1=CC=CC=N1 OXPUNWHFQLHHHF-UHFFFAOYSA-N 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
229910052903 pyrophyllite Inorganic materials 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
BACHBFVBHLGWSL-JTQLQIEISA-N rac-diclofop methyl Natural products C1=CC(O[C@@H](C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-JTQLQIEISA-N 0.000 description 1
230000005855 radiation Effects 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
235000003499 redwood Nutrition 0.000 description 1
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210000003296 saliva Anatomy 0.000 description 1
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150000003335 secondary amines Chemical class 0.000 description 1
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238000007086 side reaction Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
KEAYESYHFKHZAL-IGMARMGPSA-N sodium-23 atom Chemical compound [23Na] KEAYESYHFKHZAL-IGMARMGPSA-N 0.000 description 1
MSGMXYUAWZYTFC-UHFFFAOYSA-N sodium;2,2,2-trifluoroethanolate Chemical compound [Na+].[O-]CC(F)(F)F MSGMXYUAWZYTFC-UHFFFAOYSA-N 0.000 description 1
KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
RTVVXRKGQRRXFJ-UHFFFAOYSA-N sodium;2-sulfobutanedioic acid Chemical compound [Na].OC(=O)CC(C(O)=O)S(O)(=O)=O RTVVXRKGQRRXFJ-UHFFFAOYSA-N 0.000 description 1
HSFQBFMEWSTNOW-UHFFFAOYSA-N sodium;carbanide Chemical group [CH3-].[Na+] HSFQBFMEWSTNOW-UHFFFAOYSA-N 0.000 description 1
239000013042 solid detergent Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000002195 soluble material Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
ZDXMLEQEMNLCQG-UHFFFAOYSA-N sulfometuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=CC(C)=N1 ZDXMLEQEMNLCQG-UHFFFAOYSA-N 0.000 description 1
150000008054 sulfonate salts Chemical class 0.000 description 1
150000003461 sulfonyl halides Chemical class 0.000 description 1
230000000153 supplemental effect Effects 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000003784 tall oil Substances 0.000 description 1
235000013616 tea Nutrition 0.000 description 1
AUHNQFOFWVWFTH-UHFFFAOYSA-N tert-butyl n-(2-fluorophenyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=CC=C1F AUHNQFOFWVWFTH-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000010998 test method Methods 0.000 description 1
150000007970 thio esters Chemical group 0.000 description 1
125000004001 thioalkyl group Chemical group 0.000 description 1
150000003568 thioethers Chemical group 0.000 description 1
229940034208 thyroxine Drugs 0.000 description 1
XUIIKFGFIJCVMT-UHFFFAOYSA-N thyroxine-binding globulin Natural products IC1=CC(CC([NH3+])C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 XUIIKFGFIJCVMT-UHFFFAOYSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
231100000167 toxic agent Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
239000003440 toxic substance Substances 0.000 description 1
239000003053 toxin Substances 0.000 description 1
231100000765 toxin Toxicity 0.000 description 1
KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Chemical class OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
238000000844 transformation Methods 0.000 description 1
POFDSYGXHVPQNX-UHFFFAOYSA-N triazolo[1,5-a]pyrimidine Chemical compound C1=CC=NC2=CN=NN21 POFDSYGXHVPQNX-UHFFFAOYSA-N 0.000 description 1
UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
239000010455 vermiculite Substances 0.000 description 1
229910052902 vermiculite Inorganic materials 0.000 description 1
235000019354 vermiculite Nutrition 0.000 description 1
235000020234 walnut Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000002023 wood Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
238000004383 yellowing Methods 0.000 description 1

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CA000527878A 1983-11-14 1987-01-21 1,2,4-triazole¬1,5-a|pyrimidine-2-sulfonamides substitues et composes et methodes pour lutter contre les mauvaises herbes et empecher la nitrification de l'azote ammoniacal dans le sol Expired CA1232269A (fr)

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Application Number	Priority Date	Filing Date	Title
CA000527878A CA1232269A (fr)	1983-11-14	1987-01-21	1,2,4-triazole¬1,5-a\|pyrimidine-2-sulfonamides substitues et composes et methodes pour lutter contre les mauvaises herbes et empecher la nitrification de l'azote ammoniacal dans le sol

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US55175883A	1983-11-14	1983-11-14
US551,758		1983-11-14
CA000467616A CA1231708A (fr)	1983-11-14	1984-11-13	Derives de substitution de 1,2,4-triazolo- ¬1,5-a\|pyrimidine-2-sulfonamides; compositions et methodes pour eliminer la vegetation indesirable et empecher la nitrification de l'azote-ammonium dans le sol
CA000527878A CA1232269A (fr)	1983-11-14	1987-01-21	1,2,4-triazole¬1,5-a\|pyrimidine-2-sulfonamides substitues et composes et methodes pour lutter contre les mauvaises herbes et empecher la nitrification de l'azote ammoniacal dans le sol

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CA000467616A Division CA1231708A (fr)	1983-11-14	1984-11-13	Derives de substitution de 1,2,4-triazolo- ¬1,5-a\|pyrimidine-2-sulfonamides; compositions et methodes pour eliminer la vegetation indesirable et empecher la nitrification de l'azote-ammonium dans le sol

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Publication Number	Publication Date
CA1232269A true CA1232269A (fr)	1988-02-02

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CA000527878A Expired CA1232269A (fr)	1983-11-14	1987-01-21	1,2,4-triazole¬1,5-a\|pyrimidine-2-sulfonamides substitues et composes et methodes pour lutter contre les mauvaises herbes et empecher la nitrification de l'azote ammoniacal dans le sol

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CA (1)	CA1232269A (fr)

1987
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Publication	Publication Date	Title
CA1232276A (fr)	1988-02-02	1,2,4,-triazolo[1,5-a]pyrimidine-2-sulfonamides substitues et composes et methodes pour lutter contre les mauvaises herbes et empecher la nitrification de l'azote ammoniacal dans le sol
KR910000524B1 (ko)	1991-01-26	N-알릴설포닐-n'-피리미디닐우레아의 제조방법
KR900005370B1 (ko)	1990-07-28	설포닐 우레아의 제조방법
JP2598540B2 (ja)	1997-04-09	アルコキシ‐１，２，４‐トリアゾロ〔１，５‐ｃ〕ピリミジン‐２‐スルホンアミド，その製造法及び中間体
KR890002084B1 (ko)	1989-06-16	N-페닐설포닐-n'-피리미디닐-및-트리아지닐-우레아의 제조방법
JPS5989669A (ja)	1984-05-23	除草活性を有する尿素誘導体
CZ301369B6 (cs)	2010-02-03	Herbicidne aktivní deriváty 3-hydroxy-4-aryl-5-oxopyrazolinu
KR19990071559A (ko)	1999-09-27	N-1,2,4트리아졸로아지닐)벤젠설폰아미드및피리딘설폰아미드화합물및제초제로서의이들의용도
HU229494B1 (en)	2014-01-28	Uracil substituted phenyl sulfamoyl carboxamides
HK1001056A1 (en)	1998-05-22	1-((o-(cyclopropylcarbonyl)phenyl)sulfamoyl)-3-(4,6-dimethoxy-2-pyrimidinyl)urea and method for the preparation thereof
EP0972774A2 (fr)	2000-01-19	2-Benzylthio-8-amino(1,2,4)triazolo(1,5-a)pyridines
LT3731B (en)	1996-02-26	Sulphonylcarbamide derivatives, process for preparing thereof, intermediates, herbicidal and plant growth preventing composition, method of undesirable plants growth control
JPS6316383B2 (fr)	1988-04-08
JPH09508108A (ja)	1997-08-19	除草用アリールおよびヘテロアリールピリミジン
JPS58219179A (ja)	1983-12-20	新規スルホニル（チオ）尿素，その製造法，並びに除草および／又は生長調節用組成物
CA1211108A (fr)	1986-09-09	Ethers-oxydes phenyliques heterocycliques; preparation et agents herbicides renfermant ces composes
US4685958A (en)	1987-08-11	Sulfonamides derived from substituted 2-amino-1,2,4-triazolo[1,5-a]-1,3,5-triazines and compositions and methods of controlling undesired vegetation
JPS58219180A (ja)	1983-12-20	新規スルホニル尿素，および除草および／又は生長調節用組成物
JPH04234888A (ja)	1992-08-24	トリアゾリルスルホンアミドならびに除草性および植物生長阻害性組成物
US4290798A (en)	1981-09-22	Herbicidal compound and method of use
JPS61282365A (ja)	1986-12-12	１−アリ−ル−４−シアノ−５−ハロゲノピラゾ−ル類
AU686846B2 (en)	1998-02-12	N-pyridinyl(1,2,4)triazolo(1,5-c)pyrimidine-2-sulfonamide herbicides
HU185201B (en)	1984-12-28	Herbicide compositions containing quaternary amine salts as active substances and process for preparing the active cubstances
JPH03176475A (ja)	1991-07-31	環状尿素誘導体及び除草剤
HU186743B (en)	1985-09-30	Herbicide compositions containing alkane-carboxylic acid derivatives and process for preparing the active substances