US 5,965,490 AGranted

N-([1,2,4]triazoloazinyl)benzenesulfonamide and pyridinesulfonamide compounds and their use as herbicides

AssigneeDow AgroSciences LLC

InventorsTimothy C. Johnson, Robert J. Ehr, William A. Kleschick, Mark A. Pobanz, Richard K. Mann, John C. Van Heertum

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Abstract

N-(Triazoloazinyl)arylsulfonamide compounds, such as 2,6-dimethoxy-N-(8-chloro-5-methoxy[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)be nzenesulfonamide, 2-methoxy-4-(trifluoromethyl)-N-(5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimi din-2-yl)pyridine-3-sulfonamide, and 2-methoxy-6-methoxycarbonyl-N-(5,8-dimethoxy[1,2,4]triazolo[1,5-a]pyridin- 2-yl)benzenesulfonamide were prepared from appropriately substituted 2-amino[1,2,4]triazolo[1,5-c]pyrimidine and 2-amino[1,2,4]triazolo[1,5-a]pyridine compounds and appropriately substituted benzenesulfonyl chloride and pyridine-3-sulfonyl chloride compounds. The compounds were found to be useful as herbicides.

Claims34

Dependent claims

An N-(triazoloazinyl)arylsulfonamide compound of the formula:

##STR13## wherein X represents C--Y;
W represents O(C.sub.1 -C.sub.3 alkyl), Cl, Br, F, or H;
Y represents H, OCH.sub.3, F, Cl, Br, I, or CH.sub.3 optionally substituted with up to three fluorine atoms;
Z represents O(C.sub.1 -C.sub.3 alkyl), H, F, Cl, Br, I, S(C.sub.1 -C.sub.3 alkyl), or CH.sub.3 optionally substituted with up to three fluorine atoms;
with the proviso that at least one of W and Z represents O(C.sub.1 -C.sub.3 alkyl);
Q represents C--H or N;
A represents F, Cl, Br, or I, or CO.sub.2 (C.sub.1 -C.sub.4 alkyl) or represents C.sub.1 -C.sub.3 alkyl, O(C.sub.1 -C.sub.4 alkyl), O(C.sub.3 -C.sub.4 alkenyl), O(C.sub.3 -C.sub.4 alkynyl), or S(C.sub.1 -C.sub.3 alkyl) each optionally substituted with one O(C.sub.1 -C.sub.3 alkyl), S(C.sub.1 -C.sub.3 alkyl), chloro, bromo, or cyano substituent or with up to the maximum possible number of fluorine atoms, or represents a 2-methyl-1,3-dioxolan-2-yl moiety, and, when Q represents N, H;
B represents H, F, Cl, Br, I, NO.sub.2, CN, CO.sub.2 (C.sub.1 -C.sub.4 alkyl), NH(C.sub.1 -C.sub.3 alkyl), or N(C.sub.1 -C.sub.3 alkyl).sub.2 or represents O(C.sub.1 -C.sub.4 alkyl), O(C.sub.3 -C.sub.4 alkenyl), O(C.sub.3 -C.sub.4 alkynyl), C.sub.1 -C.sub.3 alkyl, S(C.sub.1 -C.sub.3 alkyl), SO(C.sub.1 -C.sub.3 alkyl), SO.sub.2 (C.sub.1 -C.sub.3 alkyl), S(C.sub.3 -C.sub.4 alkenyl), SO(C.sub.3 -C.sub.4 alkenyl), SO.sub.2 (C.sub.3 -C.sub.4 alkenyl), S(C.sub.3 -C.sub.4 alkynyl), SO(C.sub.3 -C.sub.4 alkynyl), or SO.sub.2 (C.sub.3 -C.sub.4 alkynyl) each optionally substituted with one O(C.sub.1 -C.sub.3 alkyl), S(C.sub.1 -C.sub.3 alkyl), chloro, bromo, or cyano substituent or with up to the maximum possible number of fluorine atoms;
with the proviso that A and B do not simultaneously represent H;
D represents H, F, Cl, Br, I, C.sub.1 -C.sub.3 alkyl, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 F, CHF.sub.2, or CF.sub.3 ;
or B and D together represent a fragment of the formula O--CH.sub.2 --O, optionally substituted with one or two F or CH.sub.3 ;
T represents H, SO.sub.2 R, C(O)R, C(O)OR, C(O)NR'.sub.2, or CH.sub.2 CH.sub.2 C (O) OR;
R represents C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, or C.sub.3 -C.sub.4 alkynyl each optionally possessing up to two chloro, bromo, O(C.sub.1 -C.sub.4)alkyl, or phenyl substituents and up to the maximum possible number of fluoro substituents;
and
R' represents H, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, or C.sub.3 -C.sub.4 alkynyl;
and, when T represents H, the agriculturally acceptable salts thereof.

13 more elements

A composition comprising an herbicidal amount of an N-(triazoloazinyl)arylsulfonamide compound of the formula:

##STR14## wherein X represents C--Y;
W represents O(C.sub.1 -C.sub.3 alkyl), Cl, Br, F, or H;
Y represents H, OCH.sub.3, F, Cl, Br, I, or CH.sub.3 optionally substituted with up to three fluorine atoms;
Z represents O(C.sub.1 -C.sub.3 alkyl), H, F, Cl, Br, I, S(C.sub.1 -C.sub.3 alkyl), or CH.sub.3 optionally substituted with up to three fluorine atoms;
with the proviso that at least one of W and Z represents O(C.sub.1 -C.sub.3 alkyl);
Q represents C--H or N;
A represents F, Cl, Br, or I, or CO.sub.2 (C.sub.1 -C.sub.4 alkyl) or represents C.sub.1 -C.sub.3 alkyl, O(C.sub.1 -C.sub.4 alkyl), O(C.sub.3 -C.sub.4 alkenyl), O(C.sub.3 -C.sub.4 alkynyl), or S(C.sub.1 -C.sub.3 alkyl) each optionally substituted with one O(C.sub.1 -C.sub.3 alkyl), S(C.sub.1 -C.sub.3 alkyl), chloro, bromo, or cyano substituent or with up to the maximum possible number of fluorine atoms, or represents a 2-methyl-1,3-dioxolan-2-yl moiety, and, when Q represents N, H;
B represents H, F, Cl, Br, I, NO.sub.2, CN, CO.sub.2 (C.sub.1 -C.sub.4 alkyl), NH(C.sub.1 -C.sub.3 alkyl), or N(C.sub.1 -C.sub.3 alkyl).sub.2 or represents O(C.sub.1 -C.sub.4 alkyl), O(C.sub.3 -C.sub.4 alkenyl), O(C.sub.3 -C.sub.4 alkynyl), C.sub.1 -C.sub.3 alkyl, S(C.sub.1 -C.sub.3 alkyl), SO(C.sub.1 -C.sub.3 alkyl), SO.sub.2 (C.sub.1 -C.sub.3 alkyl), S(C.sub.3 -C.sub.4 alkenyl), SO(C.sub.3 -C.sub.4 alkenyl), SO.sub.2 (C.sub.3 -C.sub.4 alkenyl), S(C.sub.3 -C.sub.4 alkynyl), SO(C.sub.3 -C.sub.4 alkynyl), or SO.sub.2 (C.sub.3 -C.sub.4 alkynyl) each optionally substituted with one O(C.sub.1 -C.sub.3 alkyl), S(C.sub.1 -C.sub.3 alkyl), chloro, bromo, or cyano substituent or with up to the maximum possible number of fluorine atoms;
with the proviso that A and B do not simultaneously represent H;
D represents H, F, Cl, Br, I, C.sub.1 -C.sub.3 alkyl, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 F, CHF.sub.2, or CF.sub.3 ;
or B and D together represent a fragment of the formula O--CH.sub.2 --O, optionally substituted with one or two F or CH.sub.3 ;
T represents H, SO.sub.2 R, C(O)R, C(O)OR, C(O)NR'.sub.2, or CH.sub.2 CH.sub.2 C(O)OR;
R represents C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, or C.sub.3 -C.sub.4 alkynyl each optionally possessing up to two chloro, bromo, O(C.sub.1 -C.sub.4)alkyl, or phenyl substituents and up to the maximum possible number of fluoro substituents;
and
R' represents H, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, or C.sub.3 -C.sub.4 alkynyl;
and, when T represents H, the agriculturally acceptable salts thereof in admixture with an agriculturally acceptable adjuvant or carrier.

13 more elements

A method of controlling undesirable vegetation which comprises applying to the vegetation or to the locus thereof an herbicidally effective amount of an N-(triazoloazinyl)arylsulfonamide compound of the formula:

##STR15## wherein X represents C--Y;
W represents O(C.sub.1 -C.sub.3 alkyl), Cl, Br, F, or H;
Y represents H, OCH.sub.3, F, Cl, Br, I, or CH.sub.3 optionally substituted with up to three fluorine atoms;
Z represents O(C.sub.1 -C.sub.3 alkyl), H, F, Cl, Br, I, S(C.sub.1 -C.sub.3 alkyl), or CH.sub.3 optionally substituted with up to three fluorine atoms;
with the proviso that at least one of W and Z represents O(C.sub.1 -C.sub.3 alkyl);
Q represents C--H or N;
A represents F, Cl, Br, or I, or CO.sub.2 (C.sub.1 -C.sub.4 alkyl) or represents C.sub.1 -C.sub.3 alkyl, O(C.sub.1 -C.sub.4 alkyl), O(C.sub.3 -C.sub.4 alkenyl), O(C.sub.3 -C.sub.4 alkynyl), or S(C.sub.1 -C.sub.3 alkyl) each optionally substituted with one O(C.sub.1 -C.sub.3 alkyl), S(C.sub.1 -C.sub.3 alkyl), chloro, bromo, or cyano substituent or with up to the maximum possible number of fluorine atoms, or represents a 2-methyl-1,3-dioxolan-2-yl moiety, and, when Q represents N, H;
B represents H, F, Cl, Br, I, NO.sub.2, CN, CO.sub.2 (C.sub.1 -C.sub.4 alkyl), NH(C.sub.1 -C.sub.3 alkyl), or N(C.sub.1 -C.sub.3 alkyl).sub.2 or represents O(C.sub.1 -C.sub.4 alkyl), O(C.sub.3 -C.sub.4 alkenyl), O(C.sub.3 -C.sub.4 alkynyl), C.sub.1 -C.sub.3 alkyl, S(C.sub.1 -C.sub.3 alkyl), SO(C.sub.1 -C.sub.3 alkyl), SO.sub.2 (C.sub.1 -C.sub.3 alkyl), S(C.sub.3 -C.sub.4 alkenyl), SO(C.sub.3 -C.sub.4 alkenyl), SO.sub.2 (C.sub.3 -C.sub.4 alkenyl), S(C.sub.3 -C.sub.4 alkynyl), SO(C.sub.3 -C.sub.4 alkynyl), or SO.sub.2 (C.sub.3 -C.sub.4 alkynyl) each optionally substituted with one O(C.sub.1 -C.sub.3 alkyl), S(C.sub.1 -C.sub.3 alkyl), chloro, bromo, or cyano substituent or with up to the maximum possible number of fluorine atoms;
with the proviso that A and B do not simultaneously represent H;
D represents H, F, Cl, Br, I, C.sub.1 -C.sub.3 alkyl, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 F, CHF.sub.2, or CF.sub.3 ;
or B and D together represent a fragment of the formula O--CH.sub.2 --O, optionally substituted with one or two F or CH.sub.3 ;
T represents H, SO.sub.2 R, C(O)R, C(O)OR, C(O)NR'.sub.2, or CH.sub.2 CH.sub.2 C (O) OR;
R represents C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, or C.sub.3 -C.sub.4 alkynyl each optionally possessing up to two chloro, bromo, O(C.sub.1 -C.sub.4)alkyl, or phenyl substituents and up to the maximum possible number of fluoro substituents;
and
R' represents H, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, or C.sub.3 -C.sub.4 alkynyl;
and, when T represents H, the agriculturally acceptable salts thereof.

13 more elements

Dependencies are inferred from the claim text.

Facts

Application: 09/127,384Filed 31 Jul 1998 · division
Priority: 23 Sep 1997
Granted: 12 Oct 1999
Term ends: Not estimatedThe source records don’t support an estimate.

Classification7 codes

A01N 43/90
Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds: having two or more relevant hetero rings,…
A01N 47/24
Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof: containing the groups [IMAGE cpc-sch-A01N-0944.gif], [IMAGE…
C07D 333/66
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,…:…
C07D 471/04
In which the condensed system contains two hetero rings: ortho-condensed systems