Sulphonyl urea and adjuvant based solid mixtures

Details Sulphonyl urea and adjuvant based solid mixtures Sulphonyl urea and adjuvant based solid mixtures

1999-07-13

2002-11-19

Qazi, Sabiha (Department: 1616)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S211000, C504S212000, C504S213000, C504S214000, C504S215000, C504S216000, C504S217000, C504S367000

Reexamination Certificate

active

06482772

ABSTRACT:

This application is a 371 of PCT/EP98/00201, filed on Jan. 29, 1998.
DESCRIPTION
The present invention relates to solid mixtures based on sulfonylureas and adjuvants.
Sulfonylureas (hereinafter referred to as “SUs”) are a group of highly active herbicides which are used widely in crop protection.
Since SUs are taken up through the leaves, SU activity can be improved by adding surfactants such as wetting agents to the spray liquor (cf. Green et al., ANPP, Seizième conférence du columa—Journees internationales sur la lutte contre les mauvaises herbes 1995, p. 469-474; “DPX-KG 691—A new surfactant for sulfonyl urea herbicides”).
Particularly suitable wetting agents described in the literature are, inter alia, oil adjuvants (Nalejewa et al., Weed Technol. 9 (1995), p. 689-695) or alcohol ethoxylates (see above and Dunne et al., Weed Science 42 (1994), p. 82-85; Green, Weed Technol. 7 (1993), P. 633-640). In agricultural practice, these substances are added by the farmer as tank mix additives to the spray liquor. The mixture of SU herbicide and surfactant is prepared in the spray tank just prior to use.
For example, a double pack is commercially available under the trade name CATO® (Du Pont de Nemours), comprising 25% strength water-dispersible granules of the active compound rimsulfuron (component A) and a wetting agent (component B) which is separately packed and comprises 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.
In practice, it would be desirable to be able to use ready-to-use formulations already comprising an activity-increasing wetting agent to avoid the problematic mixing immediately prior to use. In this way, it would be possible to avoid logistical problems and mixing mistakes when preparing the spray liquor. Furthermore, solid formulations are generally advantageous from a technical point of view when designing and disposing of the packaging. It is further known from the literature that SU formulations are problematic with respect to the stability of the active ingredients since, under unfavorable conditions, they may decompose over time with loss of the desired herbicidal activity. The tendency to decompose also causes problems with respect to the registration requirements, since the stability of active crop protection compounds in formulations has to meet certain minimum requirements for registration.
JP-A 62/084004 describes the use of calcium carbonate and sodium tripolyphosphate for stabilizing SU formulations.
JP-A 63/023806 claims to solve the problem by using specific carriers and vegetable oils for preparing solid SU formulations. JP-A 08/104603 describes similar effects when epoxydated natural oils are used. A common feature of these two applications is the incorporation of vegetable oils into the solid formulation to make use of the activity-enhancing properties of these adjuvants, in addition to achieving an improved stability.
Vegetable oils are incorporated into liquid formulations (generally suspension concentrates) to utilize similar effects (cf. EP-A 313317 and EP-A 554015).
It is also known from the prior art to use alkylpolyglucosides as wetting agents/adjuvants.
WO 95/2841 provides solid mixtures of an active compound and an alkylpolyglucoside adsorbed on a carrier.
EP-A 498 154 describes solid formulations of alkylpolyglycosides with the active compound N-phosphonomethylglycine.
It is an object of the present invention to provide SU solid formulations which include the adjuvant from the start and which are superior to the solid formulations of the prior art.
We have found that this object is achieved by solid mixtures comprising
a) a sulfonylurea and
b) an adjuvant from the group of the alkylpolyglycosides.
Surprisingly, it was found that the use of alkylpolyglycosides as wetting agents in SU solid formulations results in a pronounced stabilization of the active ingredient in comparison to other wetting agents (for example ethoxylated fatty amines or alcohol ethoxylates). This effect can be observed especially when water-soluble inorganic salts, such as ammonium sulfate, are present in addition to herbicidally active compounds. The stabilization is especially pronounced when the wetting agent is employed at the concentration required for biological activity.
Storage-stable ready-to-use formulations having good biological activity are obtainable by mixing the SU with other active compounds, alkylpolyglycosides and ammonium sulfate.
The invention further provides processes for preparing the solid mixtures according to the invention and their use as crop protection agents for controlling undesirable harmful plants.
Suitable sulfonylureas a) are generally compounds having the structural unit
Preference is given to SUs of the following structure I:
where J is:
 where the substituents R to R
18
are:
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
R17, 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
17
, 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
R16, S(O)
n
R
17
, 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
: 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 [sic], 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
: C
1
-C
4
-alkyl, with or without substitution 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, with or without substitution by halogen;
n is 0, 1 or 2;
L has the structure II
 where
R
j
: H or C
1
-C
3
-alkyl;
W: O or S;
X: 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: 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 [sic], 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: CH or N;
and agriculturally useful salts thereof.
Below, some suitable SUs are listed by their INN (International Nonproprietary Name) according to the Pesticide Manual:
ACC 322140;
Amidosulfuron;
Azimsulfuron (N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-1-methyl-4-(2-methyl-2H-tetrazol-5-yl)-1H-pyrazole-5-sulfonamide);
Bensulfuron-methyl (methyl 2-[[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]methyl]benzoate);
Ethyl 2-[[[[(4-chloro-6-methoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]benzoate (chlorimuron ethyl);
2-Chloro-N-[&ls

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