BR-112020022243-B1 - Concentrated suspension in aqueous capsules, containing a herbicide plant protectant and a pesticide active substance, its use and production process, ZC formulation, and method for controlling unwanted plants in agricultural crops.

BR112020022243B1BR 112020022243 B1BR112020022243 B1BR 112020022243B1BR-112020022243-B1

Abstract

Aqueous capsule suspension concentrates containing a herbicide plant protectant and a pesticide active substance. The present invention relates to aqueous capsule suspension concentrates based on 2-[(2,4-dichlorophenyl)methyl]-4,4'-dimethyl-3-isoxazolidinone and mefenpyr-diethyl, to the production thereof and to mixtures thereof with suspension concentrates of other active ingredients, and to their use as an agrochemical formulation.

Inventors

Jens Krause
STEFFEN ZANTER
Arno RATSCHINSKI
Thomas Wilde
Thomas Auler

Assignees

BAYER AKTIENGESELLSCHAFT

Dates

Publication Date: 20260310
Application Date: 20190430
Priority Date: 20180503

Claims (10)

1. A capsule-based suspension concentrate, characterized in that it comprises: (A) a particulate dispersed phase (capsule) comprising: (a) a reaction product of at least one compound with isocyanate-reactive groups (a1) and a mixture of isocyanates (a2); (b) 2-[(2,4-dichlorophenyl)methyl]-4,4'-dimethyl-3-isoxazolidinone (DCPMI); (s) a plant protection agent (s), dissolved in a water-insoluble organic solvent (L), wherein the plant protection agent (s) is mefenpyr-diethyl; and (B)(d) a liquid aqueous phase; wherein the particles of the dispersed phase (A) have an average particle size between 1 and 50 μm.
2. Concentrate in suspension in capsules, according to claim 1, characterized in that it contains one or more additives (c).
3. Concentrate in suspension in capsules, according to claim 1 or 2, characterized in that it contains at least one protective colloid (c1).
4. Concentrated suspension in capsules, according to any one of claims 1 to 3, characterized in that it contains at least one non-encapsulated active ingredient (z).
5. Process for producing concentrated suspensions in capsules, as defined in any one of claims 1 to 4, characterized in that in: step (1), a phytoprotector (s), dissolved in a water-insoluble organic solvent (L), is mixed with the isocyanate mixture (a2) and, optionally, with an organic solvent and/or emulsifier, and an active ingredient (b), dissolved in a water-insoluble organic solvent (L), is added; the solution thus prepared is then, in step (2), emulsified in water which optionally contains a protective colloid (c1), optionally in a mixture with other additives (d), and the emulsion (E) thus prepared, in step (3), is mixed with isocyanate reactive groups (a1) and then, optionally, other additives (d) are added.
6. Formulation ZC, characterized in that it comprises a concentrate in suspension in capsules, as defined in any one of claims 1 to 4, and at least one concentrate in suspension (SC), comprising: - one or more active ingredients (z), - at least one or more thickeners (c), - one or more anionic emulsifiers (e1), and/or - one or more non-ionic emulsifiers (e2).
7. ZC formulation, according to claim 6, characterized in that it comprises at least one other plant protection agent.
8. Formulation ZC, according to claim 6 or 7, characterized in that the active ingredient (z) is selected from the group consisting of flufenaceto, prosulfocarb, pendimethalin, diflufenican, aclonifene, metribuzin, piroxasulfone, propoxycarbazone, thiencarbazone-methyl, fenoxaprop, bromoxynil, halauxifene-methyl, 2,4-D, MCPA.
9. Use of the concentrates in suspension in capsules, as defined in any one of claims 1 to 4, or a ZC, as defined in any one of claims 6 to 8, characterized by the fact that it is as a herbicide in cereals and rapeseed, and, in this context, through pre-emergence and post-emergence methods.
10. A method for controlling unwanted plants in agricultural crops, characterized in that the concentrate in suspension in capsules, as defined in any one of claims 1 to 4, or a ZC, as defined in any one of claims 6 to 8, is distributed on the plants or in the area where the plants grow.

Description

[001] The present invention relates to aqueous capsule suspension concentrates based on 2-[(2,4-dichlorophenyl)methyl]-4,4'-dimethyl-3-isoxazolidinone and mefenpyr-diethyl, to the production thereof and to mixtures thereof with suspension concentrates of other active ingredients, and to their use as an agrochemical formulation. [002] Active ingredients can, in principle, be formulated in many different ways, and the properties of the active ingredients and the nature of the formulation can present problems in terms of the productability, stability, usefulness, and effectiveness of the formulations. Furthermore, particular formulations are more advantageous than others for economic and environmental reasons. [003] Due to their low and wide melting point range and amorphous structure, herbicidal plant protection products are not easy to formulate. Products on the market consist of organic dispersions, emulsion concentrates, and suspoemulsions, in which the low-melting-point active ingredient is in dissolved or emulsified form. The advantage is the rapid bioavailability of the plant protection product in dissolved form. The disadvantage is that such formulations cannot be mixed with aqueous formulations. Another disadvantage is that the plant protection product becomes bioavailable very quickly and, in some cases, is absorbed too early by the plant, so the protective effect may diminish if the active ingredient is absorbed later. A new variant described as the nearest state of the art is described in document WO 2017/144497 A1. The plant protection agent here is added to water in liquid form, crystallized, and used as a Suspension Concentrate (SC). The advantage of this SC is its miscibility with other Suspension Concentrates. A disadvantage is its miscibility with low-melting-point active ingredients in Suspension Concentrates, leading to formulation clumping. Another disadvantage compared to dissolved formulations is the lower initial bioavailability, since the particles in the concentrate must first be dissolved before being absorbed by the plant. [004] Herbicidal plant protection agents (e.g., mefenpyr-diethyl or cloquintoceto-mexilic) are frequently in the form of esterified acids which are available in their technical grade quality as a solidified melt with a melting range, which leads rapidly to agglomeration with low melting point active ingredients in finished formulations. [005] For certain active ingredients, a protectant is necessary to prevent damage to the agricultural crop. A new active ingredient on the market is the active ingredient 2-[(2,4-dichlorophenyl)methyl]-4,4'-dimethyl-3-isoxazolidinone (CAS number 81777-95-9 or IUPAC 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, hereinafter abbreviated to DCPMI). It is a chemical representative of clomazone (hereinafter abbreviated to CPMI, CAS 81777-89-1, IUPAC 2-(2-chlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one). Compared to clomazone, DCPMI has much lower water solubility (39.5 ppm instead of 1000 ppm) and a slightly lower vapor pressure (0.88 mPa compared to 19.2 mPa), and therefore the calculated Henry's Law (distribution of the active ingredient through the aqueous/gas phase) is at a similar level. Both active ingredients belong to the class of volatile active ingredients that can cause unwanted damage to neighboring crops. The low vapor pressure may also be associated with wide undesirable distribution, which should be avoided for reasons of human and environmental toxicology and for economic reasons. [006] DCPMI is used in herbicide compositions and mixtures or employed as a selective herbicide for grasses as described, for example, in documents WO-A 2015/127259 or WO-A 2012/148689. The nearest state of the art may be considered to be document WO 2018/024839 A1. [007] Therefore, it was an objective of the present invention to provide suitable encapsulation of low melting point active ingredients that is to reduce volatility by at least 70% (relative to the non-encapsulated active ingredient) and, simultaneously, lead to ideal release and action of the protector and ensure a storage-stable formulation in combination with other active ingredients. [008] Therefore, there is a need for new formulations in the form of aqueous dispersions containing a low-melting-point herbicidal phytoprotectant that has a melting temperature range that can be mixed with an active ingredient, preferably a low-melting-point active ingredient, without forming agglomerates and that have high targeted bioavailability of the phytoprotectant. [009] Furthermore, there is a need for formulations in which the phytoprotectant has been encapsulated on its own without active ingredient to ensure stable formulations in combination with low melting point active ingredient formulations. [010] Thus, it was an objective of the present invention to provide aqueous formulations comprising a phytoprotectant that does not form unwanted clumps. [011] Therefore, it was an ob