N-([1,2,4]triazoloazinyl)thiophenesulfonamide...

Details N-([1,2,4]triazoloazinyl)thiophenesulfonamide... N-([1,2,4]triazoloazinyl)thiophenesulfonamide...

2002-12-19

2003-11-11

Ford, John M. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C544S263000

Reexamination Certificate

active

06645918

ABSTRACT:

BACKGROUND OF THE INVENTION
The present invention relates to substituted thiophenesulfonamide compounds, to herbicidal compositions containing the compounds, and to the utility of the compounds for the control of unwanted vegetation.
The control of unwanted vegetation by means of chemical agents, i.e., herbicides, is an important aspect of modern agriculture and land management. While many chemicals that are useful for the control of unwanted vegetation are known, new compounds that are more effective generally, are more effective for specific plant species, are less damaging to desirable vegetation, are safer to man or the environment, are less expensive to use, or have other advantageous attributes are desirable.
Many substituted benzenesulfonamide compounds are known and certain of them are known to possess herbicidal activity. For example, certain N-([1,2,4]triazolo[1,5-a]pyrimidin-2-yl)benzenesulfonamide compounds and their herbicidal utility were disclosed in U.S. Pat. No. 4,638,075 and certain N-([1,2,4]triazolo[1,3,5]triazin-2-yl)benzenesulfonamide compounds were disclosed in U.S. Pat. No. 4,685,958. In addition, certain N-([1,2,4]triazolo[1,5-c]pyrimidin-2-yl)benzenesulfonamide, N-([1,2,4]triazolo[1,5-c]pyrimidin-2-yl)pyridinesulfonamide, N-([1,2,4]triazolo[1,5-a]pyridin-2-yl)benzenesulfonamide, and N-([1,2,4]triazolo[1,5-a]pyridin-2-yl)pyridinesulfonamide compounds were disclosed in U.S. Pat. No. 5,858,924. Certain N-phenyl arylsulfonamide compounds are also known and are known to possess herbicidal activity. For example, certain N-(substituted phenyl)[1,2,4]triazolo[1,5-c]pyrimidin-2-sulfonamide compounds were disclosed in U.S. Pat. No. 5,163,995 and certain N-(substituted phenyl)[1,2,4]triazolo[1,5-a]pyridin-2-sulfonamide compounds were disclosed in U.S. Pat. No. 5,571,775.
SUMMARY OF THE INVENTION
It has now been found that a class of novel N-(triazoloazinyl)thiophenesulfonamide compounds comprising N-([1,2,4]triazolo[1,5-c]pyrimidin-2-yl)thiophenesulfonamide, N-([1,2,4]triazolo[1,5-a]pyrimidin-2-yl)thiophenesulfonamide, and N-([1,2,4]triazolo[1,5-a]pyridin-2-yl)thiophenesulfonamide compounds are potent herbicides for the control of unwanted vegetation by either preemergence or post-emergence application. The invention includes N-(triazoloazinyl)thiophenesulfonamide compounds of Formula I:
wherein
X represents CH or
Y represents CZ or N with the proviso that X and Y are not both N;
W represents H or OR with the proviso that when Y is CZ, then W is H;
Z represents R, OR or halo;
D and E represent S or CB with the proviso that one of D or E is S;
A and B independently represent H, halo, CF
3
, R, OR′ or CO
2
R″;
T represents H, SO
2
R″, C(O)R″, C(O)OR″, C(O)NR″
2
, or CH
2
CH
2
C(O)OR″;
R represents CH
3
or CH
2
CH
3
;
R′ represents C
1
-C
4
alkyl, C
3
-C
4
alkenyl, or C
3
-C
4
alkynyl each optionally possessing up to two chloro, bromo or O(C
1
-C
4
)alkyl substituents or up to the maximum possible number of fluoro substituents;
R″ represents H or C
1
-C
4
alkyl;
and, when T represents H, the agriculturally acceptable salts thereof.
Compounds wherein A represents OR′ or B represents CO
2
R″ when D represents S and T represents H are among the preferred compounds of the invention.
The invention further includes compositions containing herbicidal amounts of compounds of Formula I in combination with one or more agriculturally acceptable adjuvants or carriers and the use of the compounds of Formula I as herbicides. The use of suitable compounds of the invention to achieve total vegetation control is generally preferred. Both grassy and broadleaf weeds can be controlled. Post-emergence application of the compounds to undesirable vegetation is generally preferred.
DETAILED DESCRIPTION OF THE INVENTION
The N-(triazoloazinyl)thiophenesulfonamide compounds of the invention can generally be described as substituted N-([1,2,4]triazolo[1,5-c]pyrimidin-2-yl)thiophenesulfonamide, N-([1,2,4]triazolo[1,5-a]pyrimidin-2-yl)thiophenesulfonamide, and N-([1,2,4]triazolo[1,5-a]pyridin-2-yl)thiophenesulfonamide compounds. They can be characterized as substituted thiophenesulfonamide compounds possessing, on the amide nitrogen atom, a substituted [1,2,4]triazolo[1,5-c]pyrimidin-2-yl, a substituted [1,2,4]triazolo[1,5-a]pyrimidin-2-yl or a substituted [1,2,4]triazolo[1,5-a]pyridin-2-yl moiety.
The herbicidal compounds of the invention are N-(triazoloazinyl)thiophenesulfonamide compounds of generic Formula I:
Such compounds in which X represents N contain a substituted N-([1,2,4]triazolo[1,5-c]pyrimidin-2-yl) moiety, those in which Y represents N contain a substituted N-([1,2,4]triazolo[1,5-a]pyrimidin-2-yl) moiety and those in which X represents C—H and Y represents C—Z contain a substituted N-([1,2,4]triazolo[1,5-a]pyridin-2-yl) moiety. Compounds in which E represents S are 2-thiophenesulfonamide compounds and compounds in which D represents S are 3-thiophenesulfonamide compounds. The compounds are further characterized by possessing a methoxy or an ethoxy substituent adjacent to the bridgehead nitrogen in the 6-membered ring portion of the triazoloazine ring and by possessing at least one substituent (A) adjacent to the sulfonamide on the thiophene ring.
The compounds of the invention include compounds of Formula I wherein X is N or CH.
Compounds in which X is N are often preferred. However, compounds in which X is CH are sometimes preferred.
The compounds of the invention include compounds of Formula I wherein Y is N, provided that X is not also N, or CZ in which Z is methyl, ethyl, methoxy, ethoxy or halo. Compounds in which Y is CZ are often preferred. However, compounds in which Y is N are sometimes preferred. Compounds in which Z is methoxy are often preferred.
Compounds of the invention include compounds of Formula I wherein D and E represent S or CB, provided that one and only one of D or E is S. The thiophene-3-sulfonamides in which D represents S are usually preferred.
Compounds of the invention include compounds of Formula I wherein A and B independently represent H, halo, CF
3
, R, OR′ or CO
2
R″. A is preferably OR′ or CO
2
R″, and most preferably OR′.
Compounds of the invention include compounds of Formula I wherein W represents H or OR provided that when Y is CZ, W is H. When Y is N, W is preferably methoxy.
For compounds of the present invention, R can be CH
3
or CH
2
CH
3
. For OR, R is preferably CH
3
.
For compounds of the present invention, R′ can be C
1
-C
4
alkyl, C
3
-C
4
alkenyl, or C
3
-C
4
alkynyl each optionally possessing up to two chloro, bromo or O(C
1
-C
4
)alkyl substituents or up to the maximum possible number of fluoro substituents. For OR′, R′ is preferably C
1
-C
4
alkyl optionally possessing up to two chloro, bromo or O(C
1
-C
4
)alkyl substituents or up to the maximum possible number of fluoro substituents.
The compounds of Formula I include those wherein T represents hydrogen, an alkylsulfonyl group (SO
2
R″), an acyl group (C(O)R″), an alkoxycarbonyl group (C(O)OR″), an aminocarbonyl group (C(O)NR″
2
), or a 2-(alkoxycarbonyl) ethyl group (CH
2
CH
2
C(O)OR″). Such compounds wherein T represents hydrogen are preferred. The invention further includes the agriculturally acceptable salts of compounds of the Formula I wherein T represents hydrogen.
For compounds of the present invention, R″ can be H or C
1
-C
4
alkyl. R″ is preferably CH
3
or CH
2
CH
3
.
Compounds of Formula I which possess each possible combination of preferred, more preferred, most preferred, desirable, and special interest s

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