Solid mixtures based on sulfonylureas and adjuvants

Details Solid mixtures based on sulfonylureas and adjuvants Solid mixtures based on sulfonylureas and adjuvants

1999-09-21

2001-06-05

Clardy, S. Mark (Department: 1616)

Plant protecting and regulating compositions

Plant growth regulating compositions

Plural active ingredients

C504S134000, C504S136000, C504S231000, C504S239000

Reexamination Certificate

active

06242382

ABSTRACT:

This application is a 371 of PCT/EP98/01441 filed Mar. 12, 1998.
The present invention relates to solid mixture ased on sulfonylureas and adjuvants.
Sulfonylureas (referred to as “SU” hereinafter) are a group of highly active herbicides which are employed in many fields of crop protection.
Due to the mechanism of active ingredient uptake via the leaf, the action of SU can be improved by adding surfactants such as wetters to the spray mixture (cf. Green et al.,ANPP, Seiziéme conference du columa—Journées internationales sur la lutte contre les mauvaises herbes 1995, pp. 469-474; “DPX-KG 691—A new surfactant for sulfonyl urea herbicides”).
Wetters which are described in the literature as being particularly suitable are, inter alia, oil adjuvants (Nalejewa et al., Weed Technol. 1995, 9, pp. 689-695) or alcohol ethoxylates (see above, and Dunne et al., Weed Science 1994, 42, pp. 82-85; Green, Weed Technol. 1993, 7, pp. 633-640). In agricultural practice, these substances are added to the spray mixture by the practitioner in the form of tank mix additives. The mixture of SU herbicide and surfactant is prepared in the spray tank only a short time before use.
An example of a commercially available product is a double pack with the trade name CATO® (Du Pont de Nemours), which is composed of 25% strength water-dispersible granules of the active ingredient rimsulfuron (component A) and a separately packaged wetter (component B) composed of a mixture of 2-butoxyethanol, polyethoxylated tallowamine and nonylphenyl polyethylene glycol ether. For use, the two components are mixed in the spray tank as described above.
It would be desirable, under practice conditions, to be able to employ readymixes which already comprise an activity-enhancing wetter so as to avoid the problem of mixing immediately prior to use. This would allow logistical problems and mixing errors to be avoided when making the spray mixture. Furthermore, readymixes are generally advantageous from the point of view of application when designing and disposing of the packaging.
It is furthermore known from the literature that formulations which comprise sulfonylureas are problematic as regards the stability of the active ingredients, since the active ingredient may undergo decomposition under unfavorable conditions in the course of time. This means that the desired herbicidal action is lost. The tendency to decomposition is also a problem with a view to the registration requirements since, for registration, the stability of crop protection agents in formulations must meet certain requirements.
JP-A 62/084004 describes the use of calcium carbonate and sodium tripolyphosphate for stabilizing SU-comprising formulations.
JP-A 63/023806 describes how the problem can be solved by using specific carriers and vegetable oils for the preparation of solid SU-comprising formulations. JP-A 08/104603 describes similar effects when using epoxydized natural oils. A shared feature of the two applications mentioned above is the incorporation of vegetable oils in the solid formulation so as to utilize the activity-enhancing effects of these substances, which act as adjuvants, in addition to an improved stability.
When incorporating vegetable oils into liquid formulations (as a rule suspension concentrates), similar effects are exploited (cf. EP-A 313317 and EP-A 554015).
It is also known from the prior art that alcohol alkoxylates together with sulfonylureas can be employed as tank mix additives.
It is an object of the present invention to provide solid formulations with sulfonylureas as active ingredients which already comprise adjuvants in the solid formulation and which are superior to solid formulations known to date.
We have found that this object is achieved according to the invention by solid mixtures which comprise
a) a sulfonylurea and
b) an adjuvant from the group of the alkyl ethers of copolymers of C
2
-C
4
-alkylene oxides.
Surprisingly, it has been found that, when using alkyl ethers of copolymers of C
2
-C
4
-alkylene oxides as wetters in SU-comprising solid-substance formulations, pronounced stabilization of the active ingredient occurs in comparison with other wetters. This effect is especially surprising because structurally related compounds such as fatty alcohol ethoxylates (see Comparison Examples 1 and 2) and ethylene oxide/propylene oxide block copolymers do not show this behavior, but, in contrast, even lead to degradation of the active ingredient. The advantageous effect can be observed especially when water-soluble inorganic salts such as ammonium sulfate are present in addition to herbicidally active ingredients. Stabilization becomes particularly pronounced when the wetter is employed at the concentration required for the biological action.
Storage-stable readymixes with good biological action can be obtained by mixing the SU with other active ingredients, alkyl ethers of copolymers of C
2
-C
4
-alkylene oxides and ammonium sulfate.
We have furthermore found processes for the preparation of the solid mixtures according to the invention and their use as crop protection products for controlling undesirable harmful plants.
Suitable as sulfonylurea a) are generally compounds with the structural unit
Preferred are SU of the following structures I:
where J has the following meanings:
where the substituents R to R
18
have the following meanings:
R: H or CH
3
;
R
1
: F, Cl, Br, NO
2
, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
3
-C
4
-cycloalkyl, C
2
-C
4
-haloalkenyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
2
-C
4
-alkoxyalkoxy, CO
2
R
12
, C(O)NR
13
R
14
, SO
2
NR
15
R
16
, S(O)
n
R
17
, C(O)R
18
, CH
2
CN or L;
R
2
: H, F, Cl, Br, CN, CH
3
, OCH
3
, SCH
3
, CF
3
or OCF
2
H;
R
3
: Cl, NO
2
, CO
2
CH
3
, CO
2
CH
2
CH
3
, SO
2
N(CH
3
)
2
, SO
2
CH
3
, SO
2
CH
2
CH
3
, OCH
3
, or OCH
2
CH
3
;
R
4
: C
1
-C
3
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
2
-C
4
-haloalkenyl, F, Cl, Br, NO
2
, CO
2
R
12
, C(O)NR
13
R
14
, SO
2
NR
15
R
16
, S(O)
n
R
l7
, C(O)R
18
or L;
R
5
: H, F, Cl, Br or CH
3
;
R
6
: C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
2
-C
4
-haloalkenyl, F, Cl, Br, CO
2
R
12
, C(O)NR
13
R
14
, SO
2
NR
15
R
16
, S(O)
n
R
l7
, C(O)R
18
or L;
R
7
: H, F, Cl, CH
3
or CF
3
;
R
8
: H, C
1
-C
4
-alkyl or pyridyl;
R
9
is C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, F, Cl, Br, NO
2
, CO
2
R
12
, SO
2
NR
15
R
16
, S(O)
n
R
17
, OCF
2
H, C(O)R
18
, C
2
-C
4
-haloalkenyl or L;
R
10
: H, Cl, F, Br, C
1
-C
4
-alkyl or C
1
-C
4
-alkoxy;
R
11
: H, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
2
-C
4
-alkoxy; haloalkenyl, F, Cl, Br, CO
2
R
12
, C(O)NR
13
R
14
, SO
2
NR
15
R
16
, S(O)
n
Rl
7
, C(O)R
18
or L;
R
12
: C
1
-C
4
-alkyl, unsubstituted or substituted by halogen, C
1
-C
4
-alkoxy or CN, allyl or propargyl;
R
13
: H, C
1
-C
4
-alkyl or C
1
-C
4
-alkoxy;
R
14
: C
1
-C
4
-alkyl;
R
15
: H, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, allyl or cyclopropyl;
R
16
: H or C
1
-C
4
-alkyl;
R
17
: C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, allyl or propargyl;
R
18
: C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl or C
3
-C
5
-cycloalkyl, unsubstituted or substituted by halogen;
n is 0.1 or 2;
L has the structure II
where
Rj is H or C
1
-C
3
-alkyl;
W is 0 or S;
X is H, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-haloalkyl, C
1
-C
4
-haloalkylthio, C
1
-C
4
-alkylthio, halogen, C
2
-C
5
-alkoxyalkyl, C
2
-C
5
-alkoxyalkoxy, amino, C
1
-C
3
-alkylamino or di(C
1
-C
3
-alkyl)amino;
Y is H, C
1
-C4-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-haloalkylthio, C
2
-C
5
-alkoxyalkyl, C
2
-C
5
-alkoxyalkoxy, amino, C
1
-C
3
-alkylamino, di(C
1
-C
3
-alkyl)-amino, C
3
-C
4
-alkenyloxy, C
3
-C
4
-alkanyloxy, C
2
-C
5
-alkylthioalkyl, C
2
-C
5
-alkylsulfinylalkyl, C
2
-C
5
-alkylsulfonylalkyl, C
1
-C
4
-haloalkyl, C
2
-C
4
-alkenyl, C
3
-C
5
-cycloalkyl, azido, fluorine or cyano;
Z is CH or N;
and the agriculturally useful salts thereof.
Some suitable SU together with their INN (International Nonproprietary Name) in accordance with Pesticide Manual may be mentioned below:
amidosulfuron;
azimsulfuron (N-[[(4,6-dimethoxy-2-

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