CA1221689A

CA1221689A - Herbicidal ortho-alkyl- and ortho-alkenyl-substituted benzenesulfonamides

Herbicidal ortho-alkyl- and ortho-alkenyl-substituted benzenesulfonamides

Info

Publication number: CA1221689A
Authority: CA; Canada
Prior art keywords: och3; loc; compound; och2ch3; locus
Prior art date: 1982-09-10
Legal status : Expired

Application number

CA000436293A

Other languages

English (en)

French (fr)

Inventor

Mark E. Thompson

Mary A. Hanagan

Current Assignee

EIDP Inc

Original Assignee

EI Du Pont de Nemours and Co

Priority date

1982-09-10

Filing date

1983-09-08

Publication date

1987-05-12

1983-09-08 Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co

1987-05-12 Application granted granted Critical

1987-05-12 Publication of CA1221689A publication Critical patent/CA1221689A/en

Status Expired legal-status Critical Current

Links

150000008331 benzenesulfonamides Chemical class 0.000 title abstract description 11
230000002363 herbicidal effect Effects 0.000 title abstract description 9
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 847
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 712
150000001875 compounds Chemical class 0.000 claims abstract description 103
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 59
101100054666 Streptomyces halstedii sch3 gene Chemical group 0.000 claims abstract description 37
229910052801 chlorine Inorganic materials 0.000 claims abstract description 32
229910052731 fluorine Inorganic materials 0.000 claims abstract description 26
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 25
150000003839 salts Chemical class 0.000 claims abstract description 25
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims abstract description 14
229910052794 bromium Inorganic materials 0.000 claims abstract description 12
229910052736 halogen Inorganic materials 0.000 claims abstract description 12
125000000217 alkyl group Chemical group 0.000 claims abstract description 10
239000001257 hydrogen Substances 0.000 claims abstract description 9
150000002367 halogens Chemical class 0.000 claims abstract description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims abstract description 5
125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims abstract description 4
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims abstract description 4
125000006519 CCH3 Chemical group 0.000 claims abstract description 4
RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 claims abstract description 4
229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 3
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 3
125000005133 alkynyloxy group Chemical group 0.000 claims abstract description 3
125000004429 atom Chemical group 0.000 claims abstract description 3
125000004773 chlorofluoromethyl group Chemical group [H]C(F)(Cl)* 0.000 claims abstract description 3
229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
125000005843 halogen group Chemical group 0.000 claims abstract 4
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract 3
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 2
125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims abstract 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 2
125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 claims abstract 2
238000000034 method Methods 0.000 claims description 74
238000006243 chemical reaction Methods 0.000 claims description 71
-1 OSO2C6H5R7 Chemical group 0.000 claims description 56
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 24
230000012010 growth Effects 0.000 claims description 15
238000002360 preparation method Methods 0.000 claims description 9
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
230000008569 process Effects 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
QSNJEJQUXVXZKE-UHFFFAOYSA-N 1-[[2-(2-methoxyethyl)phenyl]sulfonylsulfamoyl]-3-(4-methoxy-6-methylpyrimidin-2-yl)urea Chemical compound COCCC1=CC=CC=C1S(=O)(=O)NS(=O)(=O)NC(=O)NC1=NC(C)=CC(OC)=N1 QSNJEJQUXVXZKE-UHFFFAOYSA-N 0.000 claims 1
VXELKDAWRNBCDH-UHFFFAOYSA-N 2-[2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoylsulfamoyl]phenyl]ethyl 4-methylbenzenesulfonate Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)NS(=O)(=O)C=2C(=CC=CC=2)CCOS(=O)(=O)C=2C=CC(C)=CC=2)=N1 VXELKDAWRNBCDH-UHFFFAOYSA-N 0.000 claims 1
DSDCCJHGOXLAHC-UHFFFAOYSA-N 2-[2-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoylsulfamoyl]-6-sulfamoylphenyl]ethyl 4-methylbenzenesulfonate Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=C(C=CC=2)S(N)(=O)=O)CCOS(=O)(=O)C=2C=CC(C)=CC=2)=N1 DSDCCJHGOXLAHC-UHFFFAOYSA-N 0.000 claims 1
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
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238000011282 treatment Methods 0.000 description 29
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KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 23
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
239000002689 soil Substances 0.000 description 21
150000003456 sulfonamides Chemical class 0.000 description 21
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 20
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
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235000007340 Hordeum vulgare Nutrition 0.000 description 19
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