Plant protecting and regulating compositions – Plant growth regulating compositions
Reexamination Certificate
1999-08-04
2003-05-06
Qazi, Sabiha (Department: 1616)
Plant protecting and regulating compositions
Plant growth regulating compositions
C504S133000, C504S134000, C504S136000, C504S212000, C504S214000, C504S321000, C504S332000, C504S211000
Reexamination Certificate
active
06559098
ABSTRACT:
This application is a 371 of PCT/EP98/00413 filed on Feb. 4, 1998.
The present invention relates to solid mixtures based on sulfonylureas and adjuvants.
Sulfonylureas (termed “SU” hereinafter) are a group of highly active herbicides which are used widely in crop protection.
Due to the mechanism of active ingredient uptake via the leaf, it is possible to improve the activity of SU by adding surface-active substances such as wetters to the spray mixture (cf. Green et al.,ANPP, Seizieme conference du columa—Journees internationales sur la lutte contre les mauvaises herbes 1995, pp. 469-474; “DPX-KG 691—A new surfactant for sulfonylurea herbicides”).
Substances which are described in the literature as being particularly suitable wetters 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 a short time prior to use.
An example of a commercially available product is a twin pack with the trade name CATO® (Du Pont de Nemours), which is composed of water-dipersible granules in which the active ingredient rimsulfuron (component A) amounts to 25%, and of a wetter (component B) packaged separately and composed of a mixture of 2-butoxyethanol, polyethoxylated tallow amine and nonylphenyl polyethylene glycol ether. For use, the two components are mixed in the spray tank as described above.
Under practice conditions, it would be desirable to be able to employ finished formulations which already comprise an activity-enhancing wetter, so as to avoid mixing immediately prior to use, which is problematic. This would allow logistics problems and mixing errors to be avoided when making the spray mixture. Moreover, solid formulations are generally advantageous, from the point of view of application, as far as designing and disposing of the packaging is concerned.
The literature furthermore discloses that formulations which comprise sulfonlyureas are problematic with regard to active ingredient stability, since the active ingredient may undergo decomposition in the course of time when the conditions are unfavorable. If this happens, the desired herbicidal activity is lost. The tendency to decomposition is also a problem with regard to the registration requirements, since the stability of PS-type active ingredients in formulations must meet certain minimum requirements upon registration.
JP-A 62/084004 describes the use of calcium carbonate and sodium tripolyphosphate for stabilizing SU-containing formulations.
JP-A 63/023806 describes how this problem can be solved by using specific carriers and vegetable oils for the preparation of solid SU-containing formulations. JP-A 08/104603 describes similar effects when using epoxidized natural oils. The two applications mentioned above share the feature of incorporating vegetable oils into the solid formulation in order to exploit not only an improved stability, but also the activity-enhancing effects of these substances, which act as adjuvants.
Similar effects are exploited, (cf. EP-A 313317 and EP-A 554015) when incorporating vegetable oils into liquid formulations (as a rule, suspension concentrates.
It is also known from the prior art to use sulfate- or sulfonate-containing surfactants as wetters/adjuvants.
EP-A 378 895 and W092/12637 describe sulfate- or sulfonate-containing surfactants together with the active ingredient N-phosphonomethylglycine in solid formulations.
EP-A 413 267 describes the use of sulfate- or sulfonate-containing surfactants together with the active ingredients glufosinate-ammonium and fenoxaprop-ethyl.
It is an object of the present invention to provide solid formulations with sulfonylureas as active ingredients which comprise adjuvants in the solid formulation itself and which are superior to prior-art solid formulations.
We have found that this object is achieved by solid mixtures which comprise
a) a sulfonylurea and
b) an adjuvant from the group of the sulfate- or sulfonate-containing surfactants.
Surprisingly, it has been found that the use of sulfate- or sulfonate-containing surfactants as wetters in SU-containing solid formulations results in a pronounced stabilization of the active ingredient in comparison with other wetters (e.g. ethoxylated fatty amines or alcohol ethoxylates). This effect can be observed mainly when water-soluble inorganic salts, such as ammonium sulfate or potassium sulfate, are present in addition to herbicidally active ingredients. The stabilizing effect is particularly pronounced when the wetter is employed at the concentration required for the biological action.
Storage-stable finished formulations with good biological activity can be obtained by mixing the SU with other active ingredients, sulfate- or sulfonate-containing surfactants 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 compositions for controlling undesirable harmful plants.
Suitable sulfonylureas a) are generally compounds which have the structural unit
Preferred SU are those of the following structures I:
where J has the following meanings:
where the substituents R to R
18
have the following meanings:
R is H or CH
3
;
R
1
is 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
is H, F, Cl, Br, CN, CH
3
, OCH
3
, SCH
3
, CF
3
or OCF
2
H;
R
3
is 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
is 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
17
, C(O)R
18
or L;
R
5
is H, F, Cl, Br or CH
3
;
R
6
is 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
17
, C(O)R
18
or L;
R
7
is H, F, Cl, CH
3
or CF
3
;
R
8
is 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
is H, Cl, F, Br, C
1
-C
4
-alkyl or C
1
-C
4
-alkoxy;
R
11
is 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
R
17
, C(O)R
18
or L;
R
12
is C
1
-C
4
-alkyl, unsubstituted or substituted by halogen, C
1
-C
4
-alkoxy or CN, allyl or propargyl;
R
13
is H, C
1
-C
4
-alkyl or C
1
-C
4
-alkoxy;
R
14
is C
1
-C
4
-alkyl;
R
15
is H, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, allyl or cyclopropyl;
R
16
is H or C
1
-C
4
-alkyl;
R
17
is C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, allyl or propargyl;
R
18
is C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl or C
3
-C
5
-cycloalkyl, unsubstituted or substituted by halogen;
is 0, 1 or 2;
L has the structure II
where
R
j
is H or C
1
-C
3
-alkyl;
W is O 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
-C
4
-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 IN
Berghaus Rainer
Bratz Matthias
Jäger Karl-Friedrich
BASF - Aktiengesellschaft
Keil & Weinkauf
Qazi Sabiha
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