Uracil substituted phenyl sulfamoyl carboxamides

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

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C514S277000, C514S385000, C514S381000, C514S408000, C546S001000, C546S290000, C546S329000, C548S250000, C548S262200, C548S300100

Reexamination Certificate

active

06689773

ABSTRACT:

Weeds cause tremendous global economic losses by reducing crop yields and lowering crop quality. Worldwide, agronomic crops must compete with hundreds of weed species.
In spite of the commercial herbicides available today, damage to crops caused by weeds still occurs. Accordingly, there is ongoing research to create more effective and/or more selective herbicidal agents.
In WO 98/06706 are disclosed the use of certain p-trifluoromethylphenyl uracils, their method of production and their use as herbicides. In addition, WO 96/08151 discloses herbicidal aryl uracils and arylthiouracils in which the aryl ring is an optionally substituted phenyl group. In neither disclosure, however is there mentioned a sulfamoyl carboxamide group substituent.
Therefore, it was an object of the present invention to provide novel 3-phenyluracils which are highly effective for the control of undesirable plant species. The object also extends to providing novel compounds which act as desiccants/defoliants.
It was also an object of the present invention to provide a method for the control of undesirable plant species and compositions useful therefor.
It is an advantage of the present invention that the method for the control of undesirable plant species may be employed in the presence of a crop.
It was a further object of the present invention to provide a process for the preparation of herbicidal phenylsulfamoyl carboxamides and an intermediate compound useful therefor.
These and other objects and advantages of the present invention will become more apparent from the detailed description thereof set forth below.
We have found that this object is achieved in accordance with the invention by the novel uracil substituted phenylsulfamoyl carboxamides of the formula I
wherein the variables have the following meanings:
A oxygen or sulfur;
X
1
hydrogen, halogen or C
1
-C
4
-alkyl;
X
2
hydrogen, cyano, CS—NH
2
, halogen, C
1
-C
4
-alkyl or C
1
-C
4
-haloalkyl;
X
3
hydrogen, cyano, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy-alkyl, C
3
-C
7
-cycloalkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl or optionally substituted benzyl;
R
1
and R
2
independently of one another hydrogen, halogen, OR
48
, C
1
-C
10
-alkyl, C
2
-C
10
-alkenyl, C
3
-C
10
-alkynyl, C
3
-C
7
-cycloalkyl, phenyl, benzyl or C
5
-C
7
-cycloalkenyl, whereas each of the last-mentioned 7 groups can be substituted with any combination of one to six halogen atoms, one to three C
1
-C
6
-alkoxy groups, one or two C
1
-C
8
-haloalkoxy groups, one or two cyano groups, one or two C
3
-C
7
-cycloalkyl groups, one or two C(O)R
49
groups, one or two CO—OR
50
groups, one or two CO—SR
51
groups, one or two CO—NR
52
R
53
groups, one to three OR
54
groups, one to three SR
54
groups, one optionally substituted four to 10-membered monocyclic or fused bicyclic heterocyclic ring, one or two optionally substituted phenyl groups or one or two optionally substituted benzyl groups,
or R
1
and R
2
together with the atom to which they are attached form a 3- to 7-membered heterocyclic ring;
Q is selected from
wherein
A
1
to A
17
are each independently oxygen or sulfur;
R
3
, R
4
, R
7
, R
8
, R
11
, R
12
, R
18
, R
19
, R
27
, R
29
, R
32
, R
33
, R
38
, R
39
, R
44
, R
45
, R
46
and R
47
are each independently hydrogen, cyano, amino, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-haloalkoxy, C
3
-C
7
-cycloalkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-haloalkenyl, C
3
-C
6
-alkynyl, benzyl, OR
55
, C
1
-C
3
-cyanoalkyl, or
R
3
and R
4
, R
7
and R
8
, R
11
and R
12
, R
18
and R
19
or R
46
and R
47
may be taken together with the atoms to which they are attached to represent a four- to seven-membered ring, optionally interrupted by oxygen, sulfur or nitrogen and optionally substituted with one or more halogen or C
1
-C
4
-alkyl groups;
R
5
, R
6
, R
9
, R
10
, R
15
, R
16
, R
20
, R
21
, R
30
, R
31
, R
35
, R
36
, R
41
, R
42
, and R
43
are each independently hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
3
-C
7
-cycloalkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-haloalkenyl, C
3
-C
6
-alkynyl, OR
56
, S(O)
n
R
57
, O—SO
2
—R
57
, NR
58
R
59
or
R
5
and R
6
, R
9
and R
10
, R
15
and R
16
, R
20
and R
21
or R
30
and R
31
may be taken together with the atoms to which they are attached to represent a four- to seven membered ring optionally substituted with one or more halogen or C
1
-C
4
-alkyl groups;
R
13
, R
14
, R
22
, R
23
, R
25
and R
26
are each independently hydrogen, halogen or C
1
-C
6
-alkyl;
R
17
, R
28
, R
34
, R
37
or R
40
are each independently hydrogen, halogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
3
-C
7
-cycloalkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-haloalkenyl, C
3
-C
6
-alkynyl, OR
60
or SR
61
;
R
24
is hydrogen, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
2
-C
4
-alkenyl, C
3
-C
4
-alkynyl, C
1
-C
4
-haloalkoxy or amino;
R
48
, R
49
, R
50
, R
51
, R
52
, R
53
, R
54
, R
55
, R
56
, R
57
, R
58
, R
59
, R
60
and R
61
are independently of one another hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
3
-C
7
-cycloalkyl, C
2
-C
6
-alkenyl, C
3
-C
6
-alkynyl, optionally substituted phenyl or optionally substituted benzyl;
n is zero, 1 or 2;
and the agriculturally useful salts of the compounds I.
Furthermore, the invention relates to
the use of the compounds I as herbicides and/or for the desiccation/defoliation of plants,
herbicidal compositions and compositions for the desiccation/defoliation of plants which comprise compounds I as active substances,
processes for preparing the compounds I and herbicidal compositions and compositions for the desiccation/defoliation of plants using the compounds I,
methods for controlling undesirable vegetation and for the desiccation/defoliation of plants using the compounds I, and
novel intermediates of the formula II.
wherein Q, X
1
and X
2
are as defined hereinabove, with the proviso that Q must be other than Q
21
.
Preferred compounds of the formulae I and II can be seen from the sub-claims and from the description which follows.
Depending on the substitution pattern, the compounds of the formula I can contain one or more chiral centers, in which case they exist in the form of enantiomer or diastereomer mixtures. This invention provides both the pure enantiomers or diasteromers and mixtures thereof.
Agriculturally useful salts are in particular the salts of those cations and the acid addition salts of those acids whose cations and anions, respectively, do not adversely affect the herbicidal activity of the compounds I. Suitable cations are therefore in particular the ions of the alkali metals, preferably sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and the ammonium ion, which may carry one to four C
1
-C
4
-alkyl substituents, and/or one phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, and furthermore phosphonium ions, sulfonium ions, preferably tri(C
1
-C
4
-alkyl)sulfonium and sulfoxonium ions, preferably tri(C
1
-C
4
-alkyl)sulfoxonium.
Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogensulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, hydrogencarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of C
1
-C
4
-alkanoic acids, preferably formate, acetate, propionate and butyrate.
The organic moieties mentioned for the substituents X
3
and R
1
to R
61
or as radicals on phenyl or heterocyclic rings are collective terms for individual enumerations of each of the group members, as is the meaning halogen. All carbon chains, ie. all alkyl, haloalkyl, alkenyl, alkynyl and phenylalkyl moieties can be straight-chain or branched.
The terms haloalkyl, haloalkoxy and haloalkenyl as used in the specification and claims designate an alkyl group, an alkoxy group or an alkenyl group substituted with one or more halogen atoms, respectively. The halogen atoms may be the same or different.
Halogenated substituents preferably have

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