Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Reexamination Certificate
2003-03-11
2004-12-14
Clardy, S. Mark (Department: 1616)
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
C504S363000
Reexamination Certificate
active
06831041
ABSTRACT:
Oil suspension concentrates based on a cyclohexenone oxime ether lithium salt and their use as crop protection compositions.
The present invention relates to oil suspension concentrates based on 2-{1-[2-(4-chlorophenoxy)propoxyimino]butyl}-3-hydroxy-5-(tetrahydrothiopyran-3-yl)cyclohex-2-enone lithium salt and certain formulation auxiliaries, and to the use of the oil suspension concentrates as crop protection compositions, in particular as rice herbicides.
In addition to the optimization of the properties of an active compound, it is particularly important, with a view to an industrial production and use of these active compounds, to develop an efficient crop protection composition. By formulating the active compound appropriately, an optimum balance of in some cases opposed properties such as biological activity, toxicity, possible effects on the environment and costs has to be found.
In addition, the formulation has a considerable effect on the stability of a crop protection composition. This is particularly important in cases where, owing to instabilities of the active compounds or unfavorable storage conditions, the relevant requirements that a crop protection composition has to meet are particularly high.
Suspension concentrates, for example, are of great practical importance. They are liquid heterogeneous formulations of solid active compound in a liquid phase. In addition to general advantages of liquid formulations with respect to handling and meterability, for example under ULV (ultra low volume) conditions, suspension concentrates additionally frequently have good biological activity combined with relatively low phytotoxicity. Aqueous suspension concentrates are typical. However, individual cases of oily suspension concentrates have also been described, but there is the problem that many active compounds and active compound salts are soluble in the oily phase which is usually used.
Thus, WO 00/35288 describes the formulation of glyphosates or glufosinates together with cyclohexenone oxime ethers as oil suspension concentrates. In addition to the free acids, salts of the cyclohexenone oxime ethers are also considered here. However, in experiments these have been found to be unsuitable, owing to insufficient stability, as shown by the formulation of the lithium salt of 2-{1-[2-(3-chloroallyloxy)iminopropyl]-butyl}-3-hydroxy-5-(tetrahydropyran-3-yl)cyclohex-2-enone together with calcium glyphosate.
EP 0 313 317 describes oily suspension concentrates of certain sulfonylurea derivatives which can also be used in the form of their alkali metal, alkaline earth metal or ammonium salts. Vegetable oils, especially corn oil, and surfactants capable of emulsifying the vegetable oils in water are used. Similar oil-based suspension concentrates are described in U.S. Pat. No. 5,411,932. Here, too, vegetable oils, in particular corn oil and rapeseed oil, and additionally also mineral oils, and also surfactants are used for formulating a certain sulfonamide, i.e. nicosulfuron, or a salt thereof. The stability of the liquid sulfonylurea formulations, which is insufficient per se, is improved by adding urea.
Cyclohexenone oxime ethers and their metal salts are generally known useful crop protection agents. They are held in high esteem, especially as grass herbicides. The cyclohexenone oxime ether of formula (Ia) below and metal salts thereof (WO 97/20807) have been found to be particularly suitable herbicidally active compounds:
However, it is already known from EP-A 266 068 that herbicides from the substance class of the cyclohexenone oxime ethers tend to decompose. Particularly critical in this respect is the storage of corresponding crop protection formulations at elevated temperatures for a prolonged period of time. This also applies to the cyclohexenone oxime ethers of the formula (Ia) mentioned, including their metal salts.
In view of these problems, DE 195 10 887 describes storage-stable solid formulations which, in addition to a cyclohexenone oxime ether or a salt thereof, comprise certain water-soluble basic salts, in particular certain borates, phosphates, silicates, sulfites, citrates, acetates and carbonates. These are water-soluble compositions, preferably in the form of powders or granules.
For formulating certain cyclohexenone oxime ether metal salts, WO 97/20807 describes, in addition to solid formulations, also a large number of liquid formulations which are customarily employed in the area of crop protection. In this context, inert auxiliaries, such as oils, lower alcohols and strongly polar solvents, in particular water, and customary surfactants are mentioned as being substantially suitable for the formulations referred to in this publication. However, many of these auxiliaries cause, in a corresponding formulation, a rapid decomposition of the active compound.
It is an object of the present invention to provide stable liquid formulations of the cyclohexenone oxime ether of the formula (Ia) having good biological performance.
We have found that this object is achieved in the present invention by oil suspension concentrates of the corresponding lithium salt which are based on certain carboxylic esters and/or selected surfactants from the group of the sulfonates and the modified carboxylic acids.
Accordingly, the present invention provides, in particular, oil suspension concentrates comprising
(a1) 2-{1-[2-(4-chlorophenoxy)propoxyimino]butyl}-3-hydroxy-5-(tetrahydrothiopyran-3-yl)cyclohex-2-enone lithium salt of the formula (I)
and
at least one component selected from the group consisting of
(b1) at least one mono- and/or dicarboxylic ester of the formula (IIa) or (IIb)
R
1
—CO—OR
2
(IIa)
R
3
—O—CO-A
1
—CO—O—R
4
(IIb)
where R
1
is a straight-chain or branched saturated or unsaturated aliphatic radical having 6 to 30 carbons, R
2
is straight-chain or branched C
1
-C
8
-alkyl or C
3
-C
10
-cycloalkyl, A
1
is straight-chain or branched C
2
-C
6
-alkylene or C
3
-C
10
-cycloalkylene and R
3
, R
4
independently of one another are a straight-chain or branched saturated or unsaturated aliphatic radical having 1 to 24 carbons;
(c1) at least one anionic surfactant of the formula III
R
5
—SO
3
-1
M(
n+
) (III)
where M is a mono- or divalent cation (n=1 or 2) and R
5
is a straight-chain or branched aliphatic or heteroaliphatic radical having 6 to 30 carbons or a (C
6
-C
30
-alkyl)aryl radical, and
(c2) at least one nonionic surfactant of the formula (IV)
[R
6
—CO—(EO)
x
-]
y
A
2
(IV)
where R
6
is a straight-chain or branched saturated or unsaturated—optionally mono- or dihydroxylated—aliphatic radical having 8 to 30 carbons, the sum of all x being from zero to 100, y is from 1 to 7, A
2
is hydroxyl or C
1
-C
4
-alkyloxy if y is 1, or A
2
is derived from a C
3
-C
7
-polyol if y is from 2 to 7.
Accordingly, the present invention relates to liquid heterogeneous active compound-comprising formulations. They comprise solid active compound which is dispersed in an oily phase.
Oil suspension concentrates according to the invention are based on an active compound component (a) and a formulation component (F). If required, further additives may be present.
The proportion of the active component (a) in the oil suspension concentrate can be varied. It is typically in a range of from 1 to 70% by weight, preferably in a range of from 5 to 50 and in particular in a range of from 5 to 30% by weight.
In general, the stated quantities refer, unless indicated otherwise, to the total weight of the oil suspension concentrate. According to the invention, the term “substantially” generally denotes a percentage of at least 90%, preferably at least 95% and in particular at least 98%.
Terms such as alkyl, alkoxy, etc. include straight-chain and branched hydrocarbon groups, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, n-octyl, 2-ethylhexyl, n-nonyl, isononyl, n-decyl, isodecyl, n-undecyl, isoundecyl, n-do
Berghaus Rainer
Kober Reiner
Kröhl Thomas
Maywald Volker
Ziegler Hans
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