Carbamate-based solvents for agrochemical applications

Abstract

This invention relates to a composition comprising a. at least one specific carbamate-based solvent according to formula (I); and b. at least one agrochemical active ingredient. Furthermore, this invention relates to the use of such carbamate according to formula (I) as a solvent or dispersant for at least one agrochemical active ingredient, or to its use as a solvent in agrochemical formulations and corresponding methods of use.

Description

Technical Field

[0001] This invention relates to a composition comprising a. at least one urethane-based solvent according to formula (I); and b. at least one agrochemical active ingredient. Furthermore, this invention relates to the use of such urethane according to formula (I) as a solvent or dispersant for at least one agrochemical active ingredient, or to its use as a solvent in agrochemical formulations. Background Technology

[0002] In agricultural applications, a wide variety of agents are used, such as for crop protection, fertilization, and plant stimulation. Many agrochemical compositions used are in liquid form and are provided as solutions or dispersions of the active ingredient in the liquid phase (e.g., suspensions or emulsions). Therefore, solvent-based formulations are widely used in agrochemical applications. While many different solvents are used, in many cases, solvent mixtures need to be tailored to the intended use and the active ingredient. Furthermore, many known and suitable solvents have drawbacks in terms of toxicity and sustainability.

[0003] One type of solvent widely used in agrochemical applications is fatty acid dialkylamides. However, while they have many advantageous properties, they are primarily made from palm kernel and coconut oil, making them cost-intensive and exhibiting phytotoxicity to some plants.

[0004] In view of the above, there is a continued need for alternative solvents, which are preferably cost-effective, have low phytotoxicity, and provide good solubility properties.

[0005] This invention fulfills this need. Surprisingly, the inventors have discovered that certain urethane-based solvents meet these requirements and can be used as alternatives to other known solvents, such as fatty acid dialkylamides, especially in agrochemical applications and compositions.

[0006] These carbamate-based solvents exhibit good availability and solubility for a wide variety of agrochemical actives, are non-phytotoxic, and are readily formulated. It has been further found that the use of such carbamate-based solvents can help improve the performance and stability of (agrochemical) compositions containing agrochemical actives. Summary of the Invention

[0007] Therefore, in a first aspect, the present invention relates to a composition comprising

[0008] a. At least one urethane-based solvent according to formula (I)

[0009] (R 1 R2 )NC(=O)OR 3 (I)

[0010] in

[0011] R 1 and R 2 Each is independently a straight-chain or branched C1-C4 alkyl group; and

[0012] R 3 Is it a straight or branched C1-C? 10 Alkyl, R 4 -OC(=O)-R 5 Or R 4 -OR 5 ,

[0013] R 4 Is it a straight or branched C1-C? 10 -alkylene; and

[0014] R 5 It is a straight-chain or branched C1-C8 alkyl group, preferably a straight-chain or branched C1-C4 alkyl group;

[0015] The premise is that if R 3 Is it a straight or branched C1-C? 10 Alkyl group, then R 1 and R 2 Each of the following is independently a C1-C3 alkyl group, preferably methyl or ethyl, more preferably methyl; and

[0016] b. At least one agrochemical active ingredient, wherein preferably the at least one agrochemical active ingredient is not a carbamate-based solvent according to formula (I).

[0017] In various embodiments, if R 3 Is it a straight or branched C1-C? 10 Alkyl group, then R 1 and R 2 Each is independently methyl or ethyl, preferably methyl.

[0018] In various embodiments, R 1 and R 2 They are the same and preferably methyl.

[0019] In which R 3 It is R 4 -OC(=O)-R 5 Or R 4 -OR 5 In the embodiments, R 4 Preferably, it is (CH2). m(R)CH-(CH2) n Or (CH2) o -CH(R), wherein m, n and o are independent integers from 1 to 8, preferably from 1 to 4, and R is a C1-C4 alkyl, preferably methyl or ethyl.

[0020] In various embodiments,

[0021] (1) R 3 It is R 4 -OR 5 , where R 4 It is CH2-CH2, CH2-CH2-CH2, CH2-CH(R) or CH(R)-CH2, wherein R is methyl or ethyl, preferably methyl, and / or R 5 It is methyl, ethyl, propyl, or butyl; or

[0022] (2) R 3 It is R 4 -OC(=O)-R 5 , where R 4 It is CH2-CH2, CH2-CH2-CH2 or CH2-CH(R), where R is methyl or ethyl, preferably methyl, and / or R 5 It is methyl, ethyl, propyl, or butyl.

[0023] In some embodiments, R 1 and R 2 It is methyl, R 3 It is R 4 -OR 5 R 4 It is CH2-CH2, CH2-CH2-CH2, CH2-CH(CH3) or CH(CH3)-CH2, and R 5 It is methyl or butyl.

[0024] In some embodiments, R 1 and R 2 It is methyl, R 3 It is R 4 -OC(=O)-R 5 R 4 It is CH2-CH2 or CH2-CH(CH3), and R 5 It is a methyl group.

[0025] In various embodiments, R 3 Is it a straight or branched C1-C? 10 Alkyl, R 3Preferably, it is a straight-chain or branched C2-C9 alkyl group, such as a C2-C8 alkyl group, more preferably ethyl, propyl, butyl or 2-ethylhexyl, and most preferably ethyl, n-propyl or n-butyl.

[0026] Particularly preferred is that the urethane-based solvent is selected from at least one compound from the following list:

[0027]

[0028] In various embodiments, at least one agricultural chemical active ingredient is selected from the group consisting of: pest control agents, fungicides, insecticides, nematicides, herbicides, safeners, nitrification inhibitors, urease inhibitors, plant growth regulators, micronutrients, biopesticides, and / or growth regulators. Mixtures of any one or more of the foregoing substances are also included.

[0029] In various embodiments, the at least one agrochemically active ingredient is selected from the group consisting of: azoxystrobin, tebuconazole, ethoxyflufenoxam, oxadiazon, cyclohexidine, prothioconazole, fluthiamethoxam, imidacloprid, difenoconazole, pyraclostrobin, and mixtures thereof, more preferably azoxystrobin, prothioconazole, ethoxyflufenoxam, difenoconazole, tebuconazole, and mixtures thereof.

[0030] In various embodiments, the composition comprises at least one additional compound selected from the group consisting of: cosolvents, dispersants, auxiliaries, surfactants, thickeners, wetting agents, antioxidants, colorants, fragrances, defoamers, anti-caking agents, emulsifiers, and mixtures thereof.

[0031] Preferably,

[0032] - At least one cosolvent is selected from fatty acid methyl esters, aromatic hydrocarbons, 2-ethylhexanol esters, dimethyl fatty amides, dimethyl alkyl amides, fatty alcohols, glycols, alkyl esters, lactates, alkylpyrrolidones, paraffin mineral oils, vegetable oils, lactones, carbonates, urethanes, alkylamides, ketones, phosphate esters, aldehydes, ethers, acetals, and mixtures thereof, other than urethane-based solvents having formula (I); and / or

[0033] - The emulsifier is selected from nonionic or anionic surfactants and mixtures thereof, optionally...

[0034] Castor oil ethoxylates, fatty acid alkoxylates, alcohol alkoxylates, alkylamine alkoxylates, polyether copolymers, sorbitol ethoxylates, aromatic alcohol alkoxylates, alkylbenzene sulfonates or (dioctyl) sulfosuccinates.

[0035] In various embodiments, the composition comprises

[0036] a. At least one urethane-based solvent according to formula (I), in an amount of 1 to 99 wt.-%, preferably 5 to 90 wt.-%, more preferably 10 to 70 wt.-%, such as about 45 wt.-%, about 50 wt.-%, about 55 wt.-%, about 60 wt.-%, or about 63 wt.-%.

[0037] b. At least one agrochemical active ingredient, in an amount of 1 to 50 wt.-%, preferably 10 to 40 wt.-%, more preferably 15 to 30 wt.-%, such as about 20 wt.-% or about 25 wt.-%; and, optionally,

[0038] c. At least one additional compound, preferably selected from cosolvents, surfactants, auxiliaries and / or emulsifiers, in an amount of 0 to 90 wt.-%, preferably 0.1 to 70 wt.-%, more preferably 1 to 50 wt.-%; and / or

[0039] d. Water, preferably added to 100 wt.%;

[0040] Each is based on the total weight of the composition.

[0041] In a preferred embodiment, the composition according to the invention is an agricultural chemical composition.

[0042] In another aspect, the present invention relates to the use of carbamates according to formula (I) as solvents or dispersants for at least one agrochemically active ingredient.

[0043] In another aspect, the present invention relates to the use of carbamates according to formula (I) as solvents in agrochemical formulations (such as concentrates, including emulsion concentrates, suspension concentrates, and dispersion concentrates). In preferred embodiments, carbamates are able to maintain or improve the emulsion / suspension / dispersion stability of emulsion / suspension / dispersion concentrates or emulsion / suspension / dispersion formulations, preferably compared to other solvents such as N,N-dimethyldecanoic acid, alkyl esters such as 2-ethylhexyl acetate, and aromatic solvents such as naphtha (available under the trade name Solvesso™).

[0044] The use of the compositions disclosed herein for controlling pests in plants also constitutes part of this invention, including applying the compositions of the invention to said plants, to the soil in which they grow, or to their seeds.

[0045] The present invention also covers methods of using the carbamates disclosed herein as solvents for agricultural chemically active substances and methods of using the compositions described herein for controlling pests in plants, including applying the compositions of the present invention to said plants, to the soil in which they grow, or to their seeds.

[0046] In yet another embodiment, the present invention relates to compounds 3-methoxypropyl-N,N-dimethylcarbamate and / or 2-acetylpropyl-N,N-dimethylcarbamate and methods for their synthesis.

[0047] These and other aspects, embodiments, features, and advantages of the invention will become apparent to those skilled in the art from the following detailed description and claims. Each feature from one aspect of the invention can be used in any other aspect of the invention. Furthermore, the examples contained herein are intended to describe and illustrate the invention, but are not intended to limit it. In particular, the invention is not limited to these examples. Attached Figure Description

[0048] Figure 1 The water-soluble 2-methoxyethyl-N,N-dimethylcarbamate (compound D) and N,N-dimethylcarbamate acetylethyl ester (compound G) are shown to have improved solution properties compared to 2-hydroxyethyl N,N-dimethylcarbamate (L).

[0049] Figure 2 Hydrophobic n-butyl-N,N-dimethylcarbamate (CAS: 7304-97-4) (compound C) and n-propyl-N,N-dimethylcarbamate (compound B) are shown to have solution properties similar to or improved upon those of N,N-dimethyldecanoamide (compound M). Detailed Implementation

[0050] Unless otherwise expressly stated, all technical and scientific terms used herein have the meanings commonly understood in the art.

[0051] Unless the context clearly indicates otherwise, the singular form “a / an” also includes the corresponding plural form.

[0052] As used herein, “at least one” means one or more, i.e., one, two, three, four, five, six, seven, eight, nine, or more of the mentioned substances. Similarly, as used herein, “one or more” refers to at least one and includes one, two, three, four, five, six, seven, eight, nine, or more. With respect to a given substance, this term does not refer to the total number of molecules, but rather to the type of substance. Thus, “at least one urethane-based solvent” means, for example, that one type of urethane-based solvent or two or more different types of urethane-based solvents may be present. Regarding quantity, this term refers to the total amount of the mentioned substances.

[0053] Unless otherwise defined, a value for which no decimal places are specified here refers to a complete value for which one decimal place is specified, i.e., 99% means 99.0%.

[0054] Unless otherwise explicitly stated, all percentages given herein relating to compositions or formulations refer to weight % (wt.-%) relative to the total weight of the corresponding composition or formulation. Numerical ranges specified in the “x to y” format include the specified values. If multiple preferred numerical ranges are specified in this format, it should be understood that all ranges resulting from combining different endpoints are also included.

[0055] The numerical terms “about,” “approximately,” or “approx.” refer to a change of ±10%, preferably ±5%, relative to a given numerical value.

[0056] It should be understood that the term "comprising" is not limiting. For the purposes of this invention, the term "consisting of" is considered a preferred embodiment of the term "made up of". If a group is defined below as including at least a certain number of embodiments, it means that it also includes a group that preferably consists only of those embodiments.

[0057] Furthermore, the terms “first,” “second,” “third,” or “a.,” “b.,” “c.,” “d.,” “(1),” “(2),” etc., used in the specification and claims are used to distinguish similar elements and are not necessarily used to describe a sequential or chronological order. It should be understood that such terms are interchangeable where appropriate, and the embodiments of the invention described herein can be operated in orders other than those described or shown herein. In cases where the terms “first,” “second,” “third,” or “a.,” “b.,” “c.,” “d.,” “(1),” “(2),” etc., relate to steps of a method or use or measurement, there is no temporal or time interval coherence between these steps unless otherwise indicated in this application as stated above or below; that is, these steps may be performed simultaneously or there may be time intervals of seconds, minutes, hours, days, weeks, months, or even years between such steps.

[0058] It should be understood that the present invention is not limited to the specific methods, schemes, reagents, etc., described herein, as these can vary. It should also be understood that the terminology used herein is for the purpose of describing specific embodiments only and is not intended to limit the scope of the invention, which will be limited only by the appended claims.

[0059] In a first aspect, the present invention relates to a composition comprising

[0060] a. At least one urethane-based solvent according to formula (I)

[0061] (R 1 R 2 )NC(=O)OR 3 (I)

[0062] in

[0063] R 1 and R 2 They are C1-C4 alkyl groups that are either straight-chain or branched, and are independent of each other;

[0064] R 3 Is it a straight or branched C1-C? 10 Alkyl, R 4 -OC(=O)-R 5 Or R 4 -OR 5 ;

[0065] R 4 Is it a straight or branched C1-C? 10 -alkylene; and

[0066] R 5It is a straight-chain or branched C1-C8 alkyl group, preferably a straight-chain or branched C1-C4 alkyl group;

[0067] The premise is that if R 3 Is it a straight or branched C1-C? 10 Alkyl group, then R 1 and R 2 Each of the following is independently a C1-C3 alkyl group, preferably methyl or ethyl, most preferably methyl; and

[0068] b. At least one agricultural chemical active ingredient.

[0069] The urethane-based solvent (a.) according to the invention is a urethane having formula (I), which is preferably derived from the reaction of a carbonate and an amine. The preparation of urethanes is well known in the art.

[0070] As used herein, "solvent" in relation to the compositions of the present invention refers to a compound that is liquid under standard conditions (20°C, 1013 mbar) and suitable for dissolving at least one active ingredient as described herein. Therefore, it is preferable that at least one active ingredient as described below has a solubility in the solvent of at least 1 g / 100 mL, preferably 1 g / 10 mL (at 20°C).

[0071] As used herein, the term "liquid" refers to compounds and compositions that are liquid under standard conditions (20°C, 1013 mbar).

[0072] In various embodiments, R of equation (I) 1 and / or R 2 It is a C1-C3 alkyl group, preferably methyl or ethyl, and most preferably methyl. Particularly preferred is R. 1 and R 2 They are the same. In such embodiments, both can be methyl. In various embodiments, R of formula (I) 1 and R 2 Methyl carbamates are preferred.

[0073] In various embodiments of the present invention, if R 3 It is R 4 -OC(=O)-R 5 Or R 4 -OR 5 ,

[0074] Then R 4 It could be (CH2) m CH(R)-(CH2) n Or (CH2) o-CH(R), where m, n, and o are independent integers from 1 to 8, preferably integers from 1 to 4, more preferably integers of 1, 2, or 3. In such embodiments, R is a C1-C4 alkyl group, more preferably methyl, ethyl, or propyl, more preferably methyl or ethyl, and most preferably methyl. In such embodiments, R 4 Therefore, it could be CH(CH3)-(CH2) n Or (CH2) o -CH(CH3). In all these embodiments, R 4 It involves attaching the -O- group of the carbamate to -OC(=O)-R. 5 or -OR 5 The divalent group.

[0075] In some preferred embodiments,

[0076] (1) R 3 It is R 4 -OR 5 , where R 4 It is CH2-CH2, CH2-CH2-CH2, CH2-CH(R) or CH(R)-CH2, wherein R is methyl or ethyl, preferably methyl, and / or R 5 It is methyl, ethyl, propyl, or butyl, preferably methyl or butyl; or

[0077] (2) R 3 It is R 4 -OC(=O)-R 5 , where R 4 It is CH2-CH2, CH2-CH2-CH2 or CH2-CH(R), where R is methyl or ethyl, preferably methyl, and / or R 5 It is methyl, ethyl, propyl or butyl, preferably methyl.

[0078] R is particularly preferred. 1 and R 2 It is methyl, R 3 It is R 4 -OR 5 And R 4 It is CH2-CH2, CH2-CH2-CH2, CH2-CH(CH3) or CH(CH3)-CH2, and R 5 It is methyl or butyl.

[0079] In various other preferred embodiments, it is preferred that R 1 and R 2 It is methyl, R 3 It is R 4 -OC(=O)-R 5 R4 It is CH2-CH2 or CH2-CH(CH3), and R 5 It is a methyl group.

[0080] In various other preferred embodiments, if R has a carbamate-based solvent of formula (I) 3 Is it a straight or branched C1-C? 10 Alkyl group, then R 3 It is a straight-chain or branched C2-C9 alkyl group, such as a C2-C8 alkyl group, preferably ethyl, propyl, butyl, or 2-ethylhexyl, such as ethyl, n-propyl, or n-butyl. In a preferred embodiment, R 3 It is ethyl, n-propyl, n-butyl, or 2-ethylhexyl, and R 1 and R 2 Preferably, it is methyl or ethyl, with methyl being the most preferred.

[0081] In various embodiments, if R 3 Is it a straight or branched C1-C? 10 Alkyl group, then R 1 and R 2 Each is independently methyl or ethyl, preferably methyl. In various embodiments, if R 3 If it is a straight-chain or branched C6 or C8 alkyl group, then R 1 and R 2 It's not n-propyl.

[0082] In various embodiments, the urethane-based solvent is any of the compounds shown in Table 1 below.

[0083] Table 1: Carbamate-based solvent compounds according to the present invention.

[0084]

[0085] In some preferred embodiments, the urethane-based solvent is a solvent having the formula... 2-Methoxyethyl-N,N-dimethylcarbamate.

[0086] In some other preferred embodiments, the carbamate-based solvent is having the formula n-Butyl-N,N-dimethylcarbamate.

[0087] In other preferred embodiments, the carbamate-based solvent is a solvent having the formula... n-propyl-N,N-dimethylcarbamate.

[0088] In another preferred embodiment, the carbamate-based solvent is a solvent having the formula... Ethyl-N,N-dimethylcarbamate.

[0089] In various embodiments, the urethane-based solvent is water-soluble.

[0090] In various other embodiments, the urethane-based solvent is hydrophobic. A preferred example of such a hydrophobic urethane-based solvent is n-butyl-N,N-dimethylurethane (compound 9 in Table 1). This solvent is particularly suitable for emulsion formulations or emulsion concentrates. In particular, it has been found that this solvent is preferably suitable for improving the stability of emulsion formulations / emulsion concentrates compared to other solvents not according to the invention.

[0091] All carbamates disclosed herein can be produced by synthetic methods well known to those skilled in the art, including methods using alcohols, amines, chloroformates, phosgene, and carbonates as starting materials. More specifically, the carbamates of the present invention can be produced by a phosgene-based method comprising the steps of: combining a corresponding monohydric alcohol with phosgene to produce the corresponding chloroformate, and in a second step by adding the corresponding (alkyl)amine to produce the carbamate. Alternatively, carbamates can also be produced by a carbonate-based method using an amine and a cyclic carbonate (such as propylene carbonate), followed by conversion of the terminal hydroxyl group to the corresponding ester by reaction with an acid or anhydride. The latter method is also exemplarily described in EP 2327302 A1. These procedures are disclosed in more detail in the examples. The exemplary methods can be applied more generally to the synthesis of all carbamates disclosed herein.

[0092] As used in the context of this invention, an emulsion (formulation) is preferably a finely dispersed or distributed mixture of immiscible liquids. The emulsion can be o / w or w / o. Emulsions and their preparation are well known to those skilled in the art.

[0093] In this context, "emulsion concentrate" refers to a concentrated emulsion formulation / composition that can be diluted by the end user to prepare a ready-to-use composition (emulsion) for spraying plants. Similarly, the term "suspension concentrate" and the more general term "dispersion concentrate" refer to the corresponding suspension and dispersion formulations and compositions, respectively.

[0094] The compositions of the present invention further contain one or more agrochemically active substances (b.).

[0095] This agricultural chemical is typically different from carbamate (a.), and in particular not from carbamate according to formula (I). This means that the agricultural chemical and the carbamate used as a solvent are chemically different compounds, particularly to the extent that the agricultural chemical does not conform to carbamate according to formula (I). In various embodiments, the agricultural chemical is also not a carbamate excluded by the restrictive provisions concerning carbamate (a.). In various embodiments, the agricultural chemical is therefore not a carbamate according to formula (I), wherein

[0096] R 1 and R 2 They are C1-C4 alkyl groups that are either straight-chain or branched, and are independent of each other;

[0097] R 3 Is it a straight or branched C1-C? 10 Alkyl, R 4 -OC(=O)-R 5 Or R 4 -OR 5 ,

[0098] R 4 Is it a straight or branched C1-C? 10 -alkylene; and

[0099] R 5 It is a straight-chain or branched C1-C8-alkyl group.

[0100] In various embodiments, the agricultural chemical active ingredient is not a carbamate at all.

[0101] The term "agricultural active chemical" refers to a substance that imparts the desired biological activity to a composition. Typically, agricultural active chemicals are pest control agents. Agricultural active chemicals are typically selected from fungicides, insecticides, nematicides, herbicides, safeners, nitrification inhibitors, urease inhibitors, plant growth regulators, micronutrients, biopesticides, and / or growth regulators. In one embodiment, the agricultural active chemical is an insecticide. In another embodiment, the agricultural active chemical is a herbicide. In still another embodiment, the agricultural active chemical is a fungicide.

[0102] Pesticides are generally chemical or biological agents (such as pest-killing active ingredients, compounds, compositions, viruses, bacteria, antimicrobial agents, or disinfectants) that prevent, disable, kill, or otherwise thwart pests through their effects. Target pests can include insects, plant pathogens, weeds, mollusks, birds, mammals, fish, nematodes (roundworms), and microorganisms that damage property, cause disturbances, spread diseases, or act as vectors for diseases. The term "pesticide" also includes plant growth regulators that alter the expected growth, flowering, or reproductive rate of plants; defoliants that cause leaves or other foliage to fall off the plant, generally promoting harvest; desiccants that promote the drying of living tissues, such as unwanted above-ground parts of plants; plant activators that activate plant physiological functions to defend against certain pests; safeners that reduce the unwanted herbicidal effects of pesticides on crop plants; and plant growth promoters that affect plant physiological functions, such as enhancing plant growth, biomass, yield, or any other quality parameter of the harvestable product of the crop plant.

[0103] The following list of pest control agents suitable for use in the compositions of this invention is intended to illustrate possible combinations but is not limiting:

[0104] A) Respiratory depressants

[0105] -in Q o Complex III inhibitors at the site: azoxystrobin, fenoxystrobin, eugenol, fenoxystrobin, fenoxystrobin, flufenoxystrobin, flupyraclostrobin, fenoxystrobin, mandestrobin, fenoxystrobin, fenoxystrobin, pyraclostrobin, pyraclostrobin, pyraclostrobin, pyraclostrobin, pyraclostrobin, pyraclostrobin, pyraclostrobin, chlorpyrifos, oxadixyl, imidacloprid, pyrimethanil, pyraclostrobin, tetrazoxystrobin;

[0106] -in Q i Complex III inhibitors at the site: cyazofamid, indoximetris, fenpicoxamid, pyridabenamide, pyridabenamide;

[0107] - Complex II inhibitors: [List of inhibitors follows, including: methyl methacrylate, benzyl methoxyfenozide, bifenthiophanate-methyl, cyazofamid, methyl methacrylate, methyl methacrylate, fluopyram, fluopyram, fluopyram, methyl methacrylate, pyraclostrobin, methyl methacrylate, oxychloride, fluopyram, pyraclostrobin, fluopyram, bifenthiazolinone, fluopyram, methyl methacrylate, thifluzamide, inpyrfluxam, pyrapropoyne, fluopyram, isoflucypram, triflupyridine]

[0108] - Other respiratory inhibitors: diflumetorim; nitrophenyl derivatives: fenvalerate, fenvalerate, fenvalerate, fluazinam, nitrofenoxam; ferimzone; organometallic compounds: triphenyltin salts, such as triphenyltin acetate, triphenyltin chloride, or triphenyltin hydroxide; silthiamethoxam;

[0109] - The quinone-extraquinone inhibitor stigmatellin binds to azoxystrobin (ametoctradin).

[0110] B) Sterol biosynthesis inhibitors (SBI fungicides)

[0111] -C14 demethylase inhibitors: Triazoles: azaconazole, bifenthrin, furazolidone, cyclohexazole, difenoconazole, tebuconazole, R-tebuconazole, flutriafol, cyproconazole, fluquinazole, flusilazole, fenbendazole, hexaconazole, imidacloprid, tebuconazole, cyproconazole, oximazole, paclobutrazol, tebuconazole, propiconazole, prothioconazole, silfluconazole, tebuconazole, flufenoxuron, triadimefon, triadimefon, tebuconazole, tebuconazole, fluopyram, ipfentrifluconazole, chlorfluazuron; Imidazoles: imazalil, pefurazoate, prochloraz, triflumizol; Pyrimidines, pyridines, piperazines: chlorfenapyr, pyridaben, pyrazosulfanilamide;

[0112] -δ14-reductase inhibitors: aldimorph, dodemorph, dodemorph-acetate, butylmorph, isotridecylmorph, benzyl benzoate, piperazine, spirocycline;

[0113] -3-Ketoreductase inhibitors: Cyclopyridamole, Ambroxol;

[0114] - Other sterol biosynthesis inhibitors: chlorfenapyrazole.

[0115] C) Nucleic acid synthesis inhibitors

[0116] -RNA polymerase I inhibitors: Benalaxyl, benalaxyl-M, kiralaxyl, metalaxyl, furazolidone, oxazyl;

[0117] Other nucleic acid synthesis inhibitors: oxamyl, octathione, oxaquinoline, ethirimol sulfonate, 5-fluorocytosine, isoprofenquinoline, and fluopyram.

[0118] D) Inhibitors of cell division and cytoskeleton

[0119] - Microtubule polymerization inhibitors: benomyl, carbendazim, thiabendazole, methyl thiophanate, pyridachlometyl.

[0120] Other cell division inhibitors: ethoxysulfuron, thiamethoxam, pendimethalin, fluopyram, benomyl, benzoyl sulfide, pyraclostrobin, cyazofamid, fluopyram.

[0121] E) Inhibitors of amino acid and protein synthesis

[0122] - Methionine synthesis inhibitors: mepanipyrim, pyrimethanil;

[0123] - Protein synthesis inhibitors: methimazole, kasugamycin, kasugamycin hydrochloride hydrate, midomycin, streptomycin, oxytetracycline.

[0124] F) Signal transduction inhibitors

[0125] -MAP / histidine kinase inhibitors: fluoxetine, iprodione, procymidone, vinclozolin, fludioxonil;

[0126] -Mechanism unknown: Fluorophenoxyquinoline, propoxyiodoquinoline.

[0127] G) Lipid and membrane synthesis inhibitors

[0128] - Phospholipid biosynthesis inhibitors: edifenphos, iprobenfos, pyraclostrobin, isoprothiolane.

[0129] -Lipid peroxidation: dicloran, quintozene, tecnazene, tolclofos-methyl, biphenyl, chloroneb, etridiazole.

[0130] - Compounds and fatty acids that affect cell membrane permeability: cymoxanil;

[0131] -Oxidized sterol-binding protein inhibitors: fluoxapiprolin and fluoxapiprolin.

[0132] H) Inhibitors with multi-site action

[0133] -Inorganic active substances: Bordeaux mixture, copper, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur;

[0134] -Thio- and dithiocarbamates: ferbam, mancozeb, mancozeb, metam, metiram, propineb, thiram, zineb, ziram.

[0135] - Organochlorine compounds: Dichlorophenoxyacetic acid, Chlorothalonil, Captan, Chlorpyrifos, Captan, Dichlorophenol, Hexachlorobenzene, Pentachlorophenol and its salts, Phenylphthalide, Para-methyl thiophanate;

[0136] -Guinea and others: Guanidine, dextrin, dextrin free base, biguanide salt, biguanide acetate, biguanide octylamine, biguanide octylamine triacetate, biguanide trioctylbenzene sulfonate, dithiazolinone, fluoxetine, sulfadiazine, miticide.

[0137] I) Cell wall synthesis inhibitors

[0138] - Dextran synthesis inhibitors: buprofen, polyoxin B;

[0139] - Melanin synthesis inhibitors: quinolones, tricyclazole, cyclopropionamide, dicyclomet, isoprothiolane, trifluoperoxynil;

[0140] - Cellulose synthase inhibitors: dimethomorph, flumethomorph, dimethomorph, buprofen, benzimidazole, valamid, valamid.

[0141] J) Plant defense inducers

[0142] - Araratine-type benzene-S-methyl, allylbenzol, isothiazamine, tiadinil, prohexadione-calcium; Phosphonates: tris(ethylphosphonic acid), aluminum tris(ethylphosphonate), phosphorous acid and its salts, calcium phosphonate, potassium phosphonate, potassium bicarbonate or sodium bicarbonate, dichlorobenzothiazole.

[0143] K) Unknown mode of action

[0144] - Bronitrofurazone, Cyclofenac, Cymoxanil, Dazomet, Imazalil, Diclofenac, Pyridaben, Wild Bean Blight, Wild Bean Blight Methyl Sulfate, Diphenylamine, Seed Coating Ester, Amifenpyroxime, Flumetover, Flumetylsulforim, Sulfocarb, Fluthiazolinone, Hypersensitive Protein, Chlorpyrifos, Phthalosporin, Quinoline Copper, Seboctylamine, Isobutylethoxyquinoline, Leaf Blight, Imidazin, Pyridaben, Thiamethoxam, Bromhexanil, Aminopyrifen, Flufenoxadiazam.

[0145] L) Biological pest control agents

[0146] L1) Microbial agents with antifungal, antibacterial, antiviral, and / or plant defense activator activities: Powdery mildew parasiticus, Aspergillus flavus, Bacillus buddingus, Bacillus hygroscopicus, Bacillus amyloliquefaciens, Bacillus amyloliquefaciens subsp. plantarum (also known as Bacillus bellelesi), Bacillus megaterium, Bacillus mohaiweiii, Bacillus mycosis fungiformis, Bacillus pumilus, Bacillus simplex, Bacillus halophyte, Bacillus subtilis, Bacillus amyloliquefaciens var. subtilisi, Bacillus bellelesi, Candida oligosacchari, Candida saitoana, Clavibactermegia ichiganensis (bacteriophage), Shield mold, Cryptococcus parasiticus, Cryptococcus albus, Dilophosphora alopecuri, Fusarium oxysporum, Clonecrophys rosea f. catenulate (also known as Gliocladium) (catenulatum), pink bromoxynil, antibiotic lysinophil, mycolytic bromoxynil, drupocytosaccharomyces, microdochium dimerum, microsporum, Muscodor albus, Bacillus vesicularis, epiphytic Bacillus, polymyxa, pantothecin, Penicillium barometz, *Pseudomonas* species, *Pseudomonas leucosus*, *Pseudozyma flocculosa*, *Pichia aberrant*, *Pythium oligandrum*, *Sphaerodes mycoparasitica*, *Streptomyces glaucum*, *Streptomyces lidiflorus*, *Streptomyces purpureus*, *Trichoderma asperelloides*, *Trichoderma spp.*, *Trichoderma pellucida*, *Trichoderma galbana*, *T. harmatum*, *Trichoderma harzianum*, *T. polysporum*, *T. streptococcus*. stromaticum), Trichoderma virens, Trichoderma viride, Typhula phacorrhiza, Odman's sclerotium, Verticillium dahliae, and small zucchini yellow mosaic virus (non-virulent strain).

[0147] L2) Biochemical pest control agents with antifungal, antibacterial, antiviral and / or plant defense activator activities: hypersensitive protein, Polygonum cuspidatum extract.

[0148] L3) Microbial biocides with insecticidal, acaricidal, snailicidal, and / or nematode-killing activities: *Agrobacterium radiata*, *Bacillus cereus*, *Bacillus stolonifer*, *Bacillus thuringiensis*, *Bacillus thuringiensis* subsp. *catella*, *Bacillus thuringiensis* subsp. *israelina*, *Bacillus thuringiensis* subsp. *wax borer*, *Bacillus thuringiensis* subsp. *kulstaq*, *Bacillus thuringiensis* subsp. *tenaclerosa*, *Beauveria bassiana*, *Beauveria bassiana*, *Burkholderia* species, *Chromobacterium subtsugae*, codling moth granulovirus, *pseudocodling moth granulovirus*, *Flavobacterium* species, *Bollworm nucleopolyhedrovirus*, *Cornus maculatus* nucleopolyhedrovirus, *Cornus maculatus* monochroa nucleopolyhedrovirus, *Heterobacter bacteriophages*, *Cyclophorus rosenbergii*, *Lecanicillium*. *L. longisporum*, *L. muscarium*, *Metarhizium anisopliae*, *Metarhizium anisopliae microsporum*, *Metarhizium anisopliae locust*, *Nomura leishmania*, *Paecilomyces rosenbergii*, *Paecilomyces lilacinus*, *Bacillus japonicus*, *Bacillus pastoris* species, *Paecilomyces szawa*, *Paecilomyces punctata*, *P. ramosa*, *P. thornea*, *P. usgae*, *Pseudomonas fluorescens*, *Grey-winged noctuid moth nucleopolyhedrovirus*, *Skirmiceia skeletalina*, *Skirmiceia skeletalina*, *Skirmiceia skeletalina*, *Streptomyces flavus*, *Streptomyces flavus*.

[0149] L4) Biochemical pest control agents with insecticidal, acaricidal, snail-killing, pheromone-based, and / or nematicidal activities: L-carvone, citral, (E,Z)-7,9-dodecadien-1-yl acetate, ethyl formate, (E,Z)-2,4-decadienoic acid ethyl ester (pear ester), (Z,Z,E)-7,11,13-hexadecanetrienal, heptyl butyrate, isopropyl myristate, lavender ester, cis-jasmone, 2-methyl-1-butanol, methyl eugenol, methyl jasmone, (E,Z)-2,13-octadecadien-1-ol, acetic acid (E,Z) -2,13-octadecadien-1-ol ester, (E,Z)-3,13-octadecadien-1-ol, (R)-1-octen-3-ol, termite pheromone, (E,Z,Z)-3,8,11-tetradecadienyl acetate, (Z,E)-9,12-tetradecadien-1-ol acetate, (Z)-7-tetradecen-2-one, (Z)-9-tetradecen-1-ol acetate, (Z)-11-tetradecenal, (Z)-11-tetradecen-1-ol, Chenopodium ambrosiodes extract, neem oil, Quilay extract.

[0150] L5) Microbial pest control agents with plant stress reduction, plant growth regulator, plant growth promotion and / or yield increase activities: Azotobacter agalactiae, Azotobacter brasiliensis, Azotobacter lipophila, Azotobacter iridozoensis, Azotobacter high-salt, Slow-growing rhizobia species, Slow-growing rhizobia ehrlich, Slow-growing rhizobia soybean, Slow-growing rhizobia lilyensis, Slow-growing lupin rhizobia, Delfordia acidophila, Arbuscular mycorrhizal fungi, Mesophytic rhizobia species, Rhizobia pea biotype, Rhizobia pea clover biotype, Rhizobia pea broad bean biotype, Tropical rhizobia, Rhizobia spp. alfalfa.

[0151] O) Insecticides from categories O.1 to O.31

[0152] 0.1 Acetylcholinesterase (AChE) inhibitors: Aldicarb, fenvalerate, carbofuran, thiamethoxam, carbofuran, methyl ethyl sulfonate, carbaryl, carbamate, carbofuran, ethyl thiocarb, methyl ethyl sulfonate, chlorpyrifos, furazolidone, isoprocarb, methomyl, methomyl, chlorpyrifos, fenpyroxen, propoxur, thiamethoxam, thiophanate-methyl, chlorpyrifos, chlorpyrifos, chlorpyrifos, chlorpyrifos, chlorpyrifos, chlorpyrifos, phosmet, phosmet, dimethoate, dichlorvos, acephate, methyl chlorpyrifos, chlorpyrifos, chlorpyrifos, chlorpyrifos, chlorpyrifos, chlorpyrifos, chlorpyrifos, chlorpyrifos-S-methyl, diazinon, dichlorvos / DDVP, phosmet, dimethoate, methyl chlorpyrifos, acephate, chlorpyrifos, chlorpyrifos, chlorpyrifos, chlorpyrifos-S-methyl, diazinon, dichlorvos / DDVP, chlorpyrifos, dimethoate, methyl chlorpyrifos, chlorpyrifos, chlorpyrifos-S-methyl, diazinon, dichlorvos / DDVP, dimethoate, dimethoate, chlorpyrifos, chlorpyrifos-S-methyl, dimethoate ... Phosphate, EPN, Ethiophos, Promethazine, Valdex, Benzophos, Fenitrothion, Fenthion, Thiazolium Phosphate, Heptenphos, Cypermethrin, Isopropylamine Phosphate, O-(Methoxyaminothio-phosphoryl)salicylic acid isopropyl ester, Isoxazolium Phosphate, Malathion, Phosphamidon, Methamidophos, Phosphamidon, Phosphamidon, Dibromophos, Omethoate, Sulfonate, Parathion, Methyl Parathion, Indomethacin, Phosphamidon, Phosphamidon, Phosphamidon, Phosphamidon, Phosphamidon, Phosphamidon, Phosphamidon, Phosphamidon, Phosphamidon, Phosphamidon, Pyrazophos, Pyridazin, Pyrazophos, Pyrazophos, Pyrazidazine, Pyrazidazine, Pyrazidazine, Butylpyrimidine Phosphate, Dithion, Terbufos, Insecticidal, Ethiophos, Triazophos, Trichlorfon, Phosphamidon.

[0153] O.2 GABA-gated chloride channel antagonists: endosulfan, chlordane; acetamiprid, fipronil, butenpyram, pyrafluprole, pyriprole.

[0154] O.3 Sodium channel modulators: Flufenoxuron, Allethrin, D-cis-trans Allethrin, D-trans Allethrin, Bifenthrin, κ-Bifenthrin, Bioallethrin, Bioallethrin S-cyclopentenyl, Biobenzylfuran, Cypermethrin, Cypermethrin, β-Cypermethrin, Trifluralin, λ-Cypermethrin, γ-Cypermethrin, Cypermethrin, α-Cypermethrin, β-Cypermethrin, θ-Cypermethrin, ζ-Cypermethrin, Phenoxycyanide, Delanolyl, Alkenyl Cypermethrin, cypermethrin, fenvalerate, cypermethrin, fenvalerate, flufenoxuron, flufenoxuron, flufenoxuron, cypermethrin, bromoflufenoxuron, heptamethrin, imidacloprid, chlorfluphenoxy ...

[0155] 0.4 Nicotinic acetylcholine receptor (nAChR) agonists: acetamiprid, thiamethoxam, cyclopyridamole, dinotefuran, imidacloprid, acetamiprid, thiamethoxam; nicotine; flupyridine, flupyrflufenoxuron, trifluralin, dithiazolinium, flupyridine.

[0156] O.5 Nicotinic acetylcholine receptor allosteric activators: spinosad, ethyl spinosad.

[0157] O.6 Chloride channel activators: abamectin, emamectin benzoate, ivermectin, repiperazine, mibamectin.

[0158] O.7 Juvenile hormone mimics: acetamiprid, acetamiprid, acetamiprid; phenoxycarb, fenvalerate.

[0159] O.8 Various non-specific (multi-site) inhibitors: bromomethane and other alkyl halides; trichloronitromethane, sulfonyl fluoride, borax, tartaric acid.

[0160] O.9 Regulators of TRPV channels in string organs: Biprofen, Pymetrozine, Flufenoxuron.

[0161] O.10 Mite growth inhibitors: Tetradifon, Thiamethoxam, Fludex; Etoxazole.

[0162] O.11 Microbial disruptors of the insect midgut membrane: Bacillus thuringiensis, B. sphaericus, and their insecticidal proteins: Bacillus thuringiensis subsp. israelensis, B. sphaericus, B. thuringiensis subsp. aizawai, B. thuringiensis subsp. kurstaki, B. thuringiensis subsp. tenebrionis, Bt crop proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34 / 35Ab1.

[0163] O.12 Mitochondrial ATP synthase inhibitors: bufenozide; triazole tin, tricyclic tin, fenbutatin, dicofol, trichlorfon.

[0164] O.13 Oxidative phosphorylation decoupling agents via proton gradient interference: chlorfenapyr, DNOC, fipronil.

[0165] O.14 Nicotinic acetylcholine receptor (nAChR) channel blockers: chlorpyrifos, fenitrothion, chlorpyrifos ring, chlorpyrifos.

[0166] O.15 Chitosan biosynthesis inhibitors type 0: bis(triflufenican), flufenoxuron, diflubenzuron, flucyclobenzuron, flufenoxuron, flufenoxuron, lufenuron, flufenoxuron, polyfluorourea, flubenzuron, and chlorfenapyr.

[0167] O.16 Chitin biosynthesis inhibitor type 1: thiamethoxam.

[0168] O.17 Ecdyskin interference agent: cyromazine.

[0169] O.18 Ecdysone receptor agonists: methoxyfenozide, fenbufenozide, chlorfenapyr, furazolidone, cyclofenozide.

[0170] O.19 Octopus amine receptor agonist: Dimethicone.

[0171] O.20 Inhibitors of electron transport in mitochondrial complex III: flufenoxuron, cypermethrin, pyrimethanil, bifenazate.

[0172] O.21 Inhibitors of electron transport in mitochondrial complex I: quinclorac, azoxystrobin, pyrimethanil, pyridaben, pyridaben, acetamiprid, rotenone.

[0173] 0.22 Voltage-dependent sodium channel blockers: indoxacarb, cyfluthrin.

[0174] 0.23 Acetyl-CoA carboxylase inhibitors: Spirodiclofen, Spirodiclofen, Spirodiclofen, Spirodiclofen, Spirodiclofen, Spirodiclofen diester, Spirodiclofen (spidoxamat).

[0175] O.24 Inhibitors of electron transport in mitochondrial complex IV: aluminum phosphide, calcium phosphide, phosphine, zinc phosphide, cyanide.

[0176] O.25 Inhibitors of electron transport in mitochondrial complex II: pyridaben, fenflurfen, etoxazole, pyrazolylaniline.

[0177] O.26 Rianotinamide receptor modulators: chlorantraniliprole, bromocyanamide, cyclobromocyanamide, flubendiamide, fluchlorantraniliprole; tetrachlorantraniliprole; tetrazolium acetonitrile; thiocyanate; chlorfluazuron.

[0178] O.27 String organ modulator: flunitrazepam.

[0179] O.28 GABA-gated chloride channel allosteric modulators: brofenoxam, chlorfenapyr, isoxazolidinamide.

[0180] O.29 Calcium-activated potassium channel regulator: Flufenoxuron (acynonapyr).

[0181] O.30 Flumetoquin, an inhibitor of electron transport in mitochondrial complex III at the Qi site.

[0182] 0.31 Insecticidal compounds with unknown or uncertain modes of action: aflonana, azadirachtin, sulfadiazine, benzalkonium chloride, bromopropylate, fenpyroximate, cryolite, cyprodinil, dichlorvos, trichlorfon, fenproxetil, pyrimethanil, fometoquin, flufenoxolaner, flupyradifurone, fluopyram, flurranazine, metaldehyde, oxadiazon, piperonyl butyl ether, trifluralin, fenpyroximate, trifluralin, umifoxolaner, based on Bacillus thuringiensis. The active ingredient of firmus (Votivo); trifluimidinamide; chlorpyrifos; saloran, loteranan; benzpyrimoxan; tigolaner; oxazolidinamide; cyclobutrifluram; indox; flufenoxuron; trifluimidinamide.

[0183] P) Herbicides from categories P1 to P15

[0184] P1) Inhibitors of lipid biosynthesis:

[0185] -ACC- Herbicides: haloxyfop-methyl, haloxyfop-sodium, butylbenzyl, clethodim, clodinafop-methyl, clodinafop-propargyl, thiamethoxam, cyhalofop-propargyl, cyhalofop-propargyl, haloxyf ...;

[0186] - Non-ACC herbicides: benfuresate, butylate, cycloate, cogon grass, piperazine, EPTC, pendimethalin, ethoxyfuran, tetrafluoropropionic acid, molinate, orbencarb, pebulate, bensulfanilamide, TCA, quizalofop-p-ethyl, gentamicin, and vernolate.

[0187] P2) ALS inhibitors:

[0188] - Sulfonylureas: Acrylsulfuron-methyl, Tetraazolidone, Benzosulfuron-methyl, Benzosulfuron-methyl, Chlorpyrisulfuron-methyl, Chlorpyrisulfuron, Greensulfuron, Ethersulfuron-methyl, Ciprosulfuron-methyl, Aminosulfuron-methyl, Aminosulfuron-methyl, Ethoxysulfuron-methyl, Pyrisulfuron-methyl, Flupyrsulfuron-methyl, Flupyrsulfuron-methyl, Flupyrsulfuron-methyl, Sodium Flupyrsulfuron-methyl, Formamidesulfuron-methyl, Chlorpyrsulfuron-methyl, Chlorpyrsulfuron-methyl, Azoxypyrsulfuron-methyl, Methyliosulfuron-methyl, Methyliosulfuron-methyl, Iosulfuron-methyl, Iosulfuron-methyl, Disulfuron-methyl Metazosulfuron, mesosulfuronic acid, mesosulfuron, nicosulfuron, pyrimethanil, epoximsulfuron, flumethanil, flumethanil, promethazine, flusulfuron, pyrimethanil, pyrimethanil, sulfonylsulfuron, mesosulfuron, mesosulfuron, sulfonylsulfuron, thifensulfuron, thifensulfuron, benzylsulfuron, benzylsulfuron, trifluridinesulfuron, flumethanil, flumethanil, and triflumethanil;

[0189] -Imidazolinones: imidacloprid, imidacloprid methyl methoxyfenozide, methyl imidacloprid, imidacloprid, imidacloprid nicotinic acid, imidacloprid quinolinic acid, and imidacloprid;

[0190] - Triazolopyrimidine herbicides, and sulfonyl aniline herbicides: chlorpyrifos, chlorpyrifos, dichlorpyrifos, pyrimisulfuron, diflubenzuron, sulfadiazine, penoxsulam, pyrimisulfan, and pyrimisulfan;

[0191] -Pyrimidinyl benzoate esters: bispyribac-sodium, bispyribac-sodium, pyrimidinoxime, cyclopyrimidin, pyrimidin acid, pyrimidin, pyrimidin thiophanate-methyl, pyrimidin thiophanate-sodium;

[0192] -Sulfonylaminocarbonyl-triazolone herbicides: fluoxetine, fluoxetine-sodium, propanil, propanil-sodium, thiazosulfuron acid, and thiazosulfuron;

[0193] - and fluroxypyr.

[0194] P3) Photosynthesis inhibitors:

[0195] Ampicillin, a photosystem II inhibitor, is a triazine herbicide, including chlortriazine, triazinone, triazinedione, methylthiotriazine, and pyridazinones such as atrazine, atrazine, chlormequat chloride, cyhalothrin, diquat, isoamyl acetate, cyclomethazine, cyprodinil, propargite, propargite, propargite, simazine, propargite, terbufos, terbufos, terbufos, and trietazin; arylurea, such as chlorobromopropylate, chlormequat chloride, fenflurazole, oxazolone, diuron, fenflurazole, isoproturon, isoxaflutole, linuron, benzoxazine, methylbenzylthiamethoxam, pyranolol, methoxyfenozide, and chlormequat chloride. Herbicides such as chlorpyrifos, cycloribonucleo, terbuprofen, thiamethoxam, and thiamethoxam; carbamate esters such as karbutilat, betaine, and betaine-ethyl; nitrile herbicides such as bromophenol oxime, bromobenzonitrile and its salts and esters, iodobenzonitrile and its salts and esters; uracils such as chlorpyrifos, cycloribonucleo, and terbuprofen, as well as thiamethoxam and thiamethoxam-sodium, pyridafol, pyridafol, succinate, and propargite; and photosystem I inhibitors such as diquat, diquat-dibromochlor, paraquat, paraquat-dichloride, and paraquat-dimethyl sulfate.

[0196] P4) Protoporphyrinogen-IX oxidase inhibitor:

[0197] Trifluralin, trifluralin sodium, pyrazosulfuron, benzalkonium chloride, pyrazosulfuron, methoxyfenozide, flupropargyl, pyrazosulfuron, pyrazosulfuron, methoxyfenozide, chlorimide, indole-methyl, cyprofenozide, isopyram, flupyridazine, flupyridazine ethyl ester, flupyrazosulfuron, flupyrimidine, propyzoxystrobin, ethoxysulfuron, methoxysulfuron, methyl propyzoxystrobin, flusulfanilamide, flunisulfuron, propyzoxystrobin, ethoxysulfuron, cyclopentoxane, flupyrazosulfuron, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, mesosulfuron, mesosulfuron, thiamethoxam, flupyrazosulfuron, trifluralin, flupyrazosulfuron.

[0198] P5) Bleaching agents and herbicides:

[0199] -PDS inhibitors: flubutyrazole, pyrifluquinazon, fluroxypyr, flurochloridone, furazolidone, dapoxetine, flupyroxypyr, pyrimisulfuron;

[0200] -HPPD inhibitors: benzobicyclon, benzofenap, flupyrazole, isoxaflutole, fenquinoline, isoxaflutole, mesotrione, oxotrione, pyrazolynate, pyrazoxyfen, sulfadiazine, tefuryltrione, pyrazosulfuron, pyrazosulfuron, benzopyrazole, bipyrazone, fenpyrazone, cypyrafluone, tripyrasulfone, benquitrione, dioxaflutole;

[0201] - Bleaching agents, unknown targets: aclofen, chlorpyrifos, flumeturon, bixlozone.

[0202] P6) EPSP synthase inhibitors:

[0203] Glyphosate, glyphosate-isopropylammonium, glyphosate-potassium, and glyphosate-trimethyl sulfide (glyphosate).

[0204] P7) Glutamine synthase inhibitors: Bisammoniazoline (bisammoniazoline), bisammoniazoline-sodium, glufosinate, glufosinate-ammonia and glufosinate-ammonia.

[0205] P8) DHP synthase inhibitor: asulam.

[0206] P9) Mitosis inhibitors:

[0207] -K1 group: Dinitroaniline herbicides: fluroxypyr, sec-butylpyr, dichlorophenoxypyr, etalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine, and trifluralin; Phosphoramides: acephate, acephate-methyl, and butamiphos; Benzoic acid herbicides: chlorthal, methyl chlorphthalate; Pyridines: fluthion and thiamethoxam; Benzamides: propyzamide and tebutam.

[0208] -K2 group: diclofenac, chlorfenapyr, basil, basil-isopropyl fluoride, basil-methyl fluoride, refined basil-isopropyl fluoride, refined basil-methyl fluoride and chlorfenapyr.

[0209] P10) VLCFA inhibitors:

[0210] - Chloracetamides: acetochlor, alachlor, acetaminophen, butachlor, dimethachlor, dimethenamid, dimethenamid, pyrazochlor, metolachlor, metolachlor-S, pethoxamid, pretilachlor, propisochlor, and thenylchlor.

[0211] -O-acetanilides: fluthiamethoxam and bensulfamethoxam;

[0212] - Acetanilides: diphenamid, naphthylpropane, dichlorvos, and dichlorvos;

[0213] -Tetrazolinones: fentrazamide;

[0214] Other herbicides: anilofos, cafenstrole, fenoxasulfone, ipfencarbazone, piperphos, pyroxasulfone, dimethosulfuron, and isoxazoline.

[0215] P11) Cellulose biosynthesis inhibitors: chlorthiamid, dichlobenil, flumetsulam, indazine-flumetsulam, isoxaben, triazine-flumetsulam.

[0216] P12) Decoupled herbicides: dinoterb, dinoterb, and DNOC and their salts.

[0217] P13) Plant growth regulator herbicides:

[0218] 2,4-D and its salts and esters, such as clacyfos, 2,4-DB and its salts and esters, aminocyclopyrachlor and its salts and esters, aminopyralid and its salts, such as aminopyralid-dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benzolin, chloramben and its salts and esters, clonprop, clopyralid and its salts and esters, dicamba and its salts and esters, dicamba and its salts and esters, 2,4-D propionic acid (dic... Flopyrauxifen and its salts and esters, 2,4-D-propionic acid and its salts and esters, flopyrauxifen, fluroxypyr, flopyroxypyr, flopyroxyisopropyl butyroxyl chloroxypyr, halauxifen and its salts and esters; MCPA and its salts and esters, MCPA-thioethyl ester, MCPB and its salts and esters, mecoprop and its salts and esters, flopyrauxifen and its salts and esters, florpyrauxifen and its salts and esters, florpyrauxifen and its salts and esters, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridinecarboxylic acid.

[0219] P14) Plant auxin transport inhibitors: diflufenzopyr, diflufenzopyr-sodium, naptalam, and naptalam-sodium.

[0220] P15) Other herbicides: bromobutyroxyfen, chlorfluazuron, chlorfenapyr, cyclohexane, bensulfuron, cyclopyrimorate and its salts and esters, malathion, dazomet, fenthion methyl sulfate, thiamethoxam, DSMA, chlorfluazuron, chlorfluazuron and its salts, ethoxybenzamide, chlorfluazuron, chlorfluazuron butyl ester, furazolidone, phosmet, phosmetammonium, indicarb, maleic hydrazine, flusulfuron, methyl thiophanate, methyl azide, methyl bromide, methyl chlorfluazuron, methyl iodide, MSMA, oleic acid, oxadiazon, nonanoic acid, barnyardgrass, cyhalothrin, tetraflufenoxam, cyhalothrin.

[0221] Q) Safety agent

[0222] (quinoline-8-oxy)acetic acid, 1-phenyl-5-haloalkyl-1H-1,2,4-triazol-3-carboxylic acid, 1-phenyl-4,5-dihydro-5-alkyl-1H-pyrazole-3,5-dicarboxylic acid, 4,5-dihydro-5,5-diaryl-3-isoxazolecarboxylic acid, dichloroacetamide, α-oxime-phenylacetonitrile, acetophenone oxime, 4,6-dihalo-2-phenylpyrimidine, N-[[4-(aminocarbonyl)phenyl]sulfonyl]-2-benzamide, 1,8-naphthalenedicarboxylic anhydride, 2-halo-4-(haloalkyl)-5-thiazolic acid, thiophosphates and N-alkyl-O-phenylcarbamates and their agriculturally acceptable salts and their agriculturally acceptable derivatives, such as amides, esters and thioesters, provided that they have an acid group.

[0223] In a preferred embodiment, the composition comprises at least one agrochemical active ingredient selected from the group consisting of herbicides, fungicides and insecticides, and / or at least one plant growth regulator or any combination of two or more of the foregoing.

[0224] In various embodiments, the agricultural chemical actives used according to the present invention are selected from the group consisting of triazole, ethoxyflufenoxam, cytosine, fluthiamethoxam, neonicotinoids, or mixtures thereof.

[0225] In various embodiments, the at least one agrochemically active ingredient is selected from the group consisting of: azoxystrobin, tebuconazole, ethoxyflufenoxam, oxadiazon, cyclohexidine, prothioconazole, fluthiamethoxam, imidacloprid, difenoconazole, pyraclostrobin, and mixtures thereof, preferably azoxystrobin, prothioconazole, ethoxyflufenoxam, difenoconazole, tebuconazole, and mixtures thereof.

[0226] The composition may contain at least one additional compound selected from the group consisting of: cosolvents, dispersants, auxiliaries, surfactants, thickeners, wetting agents, antioxidants, colorants, fragrances, defoamers, anti-caking agents, emulsifiers, and mixtures thereof.

[0227] Preferably, at least one cosolvent is selected from fatty acid methyl esters, aromatic hydrocarbons, 2-ethylhexanol esters, dimethyl fatty amides, dimethyl alkyl amides, fatty alcohols, glycols, alkyl esters, lactates, aromatic esters, alkylpyrrolidones, paraffin mineral oils, vegetable oils, lactones, carbonates, urethanes, alkylamides, ketones, phosphate esters, aldehydes, ethers, acetals, and mixtures thereof, which are different from urethane-based solvents having formula (I).

[0228] In various embodiments, the at least one co-solvent is selected from C 12 -C 18 Fatty acid methyl esters, aromatic hydrocarbons, or mixtures thereof.

[0229] In various embodiments, the at least one additional compound is an emulsifier and / or a surfactant. Suitable compounds include nonionic and anionic surfactants and mixtures thereof. Nonionic surfactants include, for example:

[0230] -2 to 30 mol of ethylene oxide and / or 0 to 5 mol of propylene oxide are added to the straight-chain C14. 8-22 fatty alcohols, C 12-22 Products on fatty acids and alkylphenols containing 8 to 15 carbon atoms;

[0231] -1 to 30 mol of the C-value of the addition product of ethylene oxide to glycerol 12 / 18 Fatty acid monoesters and diesters;

[0232] - Glyceryl monoesters and diesters of saturated and unsaturated fatty acids containing 6 to 22 carbon atoms, as well as sorbitol monoesters and diesters and their ethylene oxide addition products;

[0233] -15 to 60 mol of ethylene oxide addition products on castor oil and / or hydrogenated castor oil;

[0234] - Polyol esters, and especially polyglycerol esters, such as polyglycerol polyricinoleate, polyglycerol poly-12-hydroxystearate, or polyglycerol dimer isostearate. Mixtures of compounds from several of these categories are also suitable;

[0235] -2 to 15 mol of ethylene oxide addition products on castor oil and / or hydrogenated castor oil;

[0236] -Based on straight chain, branched chain, unsaturated or saturated C 6 / 22 Esters of fatty acids, ricinoleic acid and 12-hydroxystearic acid and glycerol, polyglycerol, pentaerythritol, dipentaerythritol, sugar alcohols (e.g., sorbitol), alkyl glucosides (e.g., methyl glucoside, butyl glucoside, lauryl glucoside) and polyglucosides (e.g., cellulose);

[0237] - Mono-, di- and trialkyl phosphates and mono-, di- and / or tri-PEG-alkyl phosphates and their salts;

[0238] - Lanolin;

[0239] - Polysiloxane / polyalkyl polyether copolymers and their derivatives;

[0240] - A mixture of pentaerythritol, fatty acids, citric acid, and fatty alcohols and / or C 6-22 Fatty acids, methyl glucose, and polyols are preferably mixed esters of glycerol or polyglycerol;

[0241] - Polyalkylene glycol.

[0242] The addition products of ethylene oxide and / or propylene oxide to fatty alcohols, fatty acids, alkylphenols, glycerol mono- and diesters of fatty acids, and dehydrated sorbitol mono- and diesters of fatty acids, or to castor oil, are known and commercially available products. They are homologues, and their average degree of alkoxylation corresponds to the ratio between the amount of ethylene oxide and / or propylene oxide undergoing the addition reaction and the amount of substrate. The C10 of the addition product of ethylene oxide to glycerol... 12 / 18 Fatty acid monoesters and diesters are known as lipid layer enhancers for use in cosmetic formulations. Preferred emulsifiers are described in more detail below:

[0243] In various embodiments, the emulsifier or surfactant may be a metaglycerol ester. Typical examples of suitable metaglycerol esters are glyceryl monohydroxystearate, glyceryl dihydroxystearate, glyceryl monoisostearate, glyceryl diisostearate, glyceryl monooleate, glyceryl dioleate, glyceryl monorictoside, glyceryl dirictoside, glyceryl monolinoleate, glyceryl dilinoleate, glyceryl monolinoleate, glyceryl dilinoleate, glyceryl monoethanoate, glyceryl diethanoate, glyceryl monoethanoate, glyceryl diethanoate, glyceryl monotarate, glyceryl ditaranoate, glyceryl monocitrate, glyceryl dicitrate, glyceryl monomalate, glyceryl dimalate, and industrial mixtures thereof, which may still contain a small amount of triglycerides from the production process. Addition products of 1 to 30, and preferably 5 to 10 mol, of ethylene oxide onto the aforementioned metaglycerol esters are also suitable.

[0244] In various embodiments, the emulsifier or surfactant may be a sorbitol ester. Suitable sorbitol esters are sorbitol monoisostearate, sorbitol sesquiisostearate, sorbitol diisostearate, sorbitol triisostearate, sorbitol monooleate, sorbitol sesquioleate, sorbitol dioleate, sorbitol trioleate, sorbitol monoerucate, sorbitol sesquierucate, sorbitol dierucate, sorbitol trierucate, sorbitol monoricinoleate, sorbitol sesquirucate, sorbitol trierucate, sorbitol monoricinoleate, sorbitol sesquirucate, sorbitol diricinoleate, sorbitol triricinoleate, and sorbitol monoricinoleate. Sorbitol monohydroxystearate, sorbitol sesquihydroxystearate, sorbitol dihydroxystearate, sorbitol trihydroxystearate, sorbitol monotartrate, sorbitol sesquitartrate, sorbitol ditartrate, sorbitol tritartrate, sorbitol monocitrate, sorbitol sesquicitrate, sorbitol dicitrate, sorbitol tricitrate, sorbitol monomaleate, sorbitol sesquimaleate, sorbitol dimaleate, sorbitol trimaleate, and industrial mixtures thereof. Addition products of 1 to 30, and preferably 5 to 10 mol, of ethylene oxide onto the mentioned sorbitol esters are also suitable.

[0245] In various embodiments, the emulsifier or surfactant may be an alkyl (alkenyl) oligoglycoside. Alkyl or alkenyl oligoglycosides, also representing preferred emulsifiers, may be derived from aldoses or ketoses containing 5 or 6 carbon atoms, preferably glucose. Therefore, preferred alkyl and / or alkenyl oligoglycosides are alkyl or alkenyl oligoglucosides. These materials are also commonly referred to as "alkyl polyglycosides" (APGs). The alkyl (alkenyl) oligoglycosides according to the invention conform to formula (II):

[0246] R a O[G] p (II)

[0247] Where R aIt is an alkyl or alkenyl group having 6 to 22 carbon atoms, G is a sugar unit having 5 or 6 carbon atoms, and p is a number from 1 to 10. The exponent p in general formula (III) indicates the degree of oligomerization (DP degree), i.e., the distribution of monoglycosides and oligoglycosides, and is a number from 1 to 10. However, p in a given compound must always be an integer, and most importantly, a value from 1 to 6 can be assumed. The value p of a particular alkyl oligoglycoside is a calculated value determined by analysis, which is mostly a fraction. Alkyl (alkenyl) oligoglycosides with an average degree of oligomerization p of 1.1 to 3.0 are preferred. From an application perspective, alkyl (alkenyl) oligoglycosides with an oligomerization degree below 1.7, and more particularly between 1.2 and 1.4, are preferred. Alkyl or alkenyl R a It can be derived from primary alcohols containing 4 to 22, preferably 8 to 16, carbon atoms. Typical examples are butanol, hexanol, octanol, decanol, undecanool, lauryl alcohol, myristol, cetyl alcohol, palmitol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, trans-9-octadecenol, phellandrene, arachidonicol, eicosenoyl alcohol, betaine alcohol, guarana alcohol, and industrial mixtures thereof, such as those formed, for example, in the hydrogenation of industrial fatty acid methyl esters or in the hydrogenation of aldehydes derived from Roelen carbonyl synthesis. Preferred are hydrogenated C8-C based on a DP of 1 to 3. 16 Alkyl oligoglucosides of coconut oil alcohols. Also suitable are alkoxylated products of alkyl oligoglucosides, such as 1 to 10 moles of ethylene oxide and / or 1 to 5 moles of propylene oxide with DP at a C8-C ratio between 1.2 and 1.4. 10 Or C 12 -C 18 Adducts of alkyl oligoglucosides.

[0248] In various embodiments, the emulsifier or surfactant is an alkoxylated vegetable oil. Suitable emulsifiers are castor oil, rapeseed oil, or soybean oil (Agnique CSO 35, Agnique SBO 10, Agnique SBO 60) ethoxylated with 3 to 80 moles of ethylene oxide.

[0249] In various embodiments, the emulsifier or surfactant is an alkoxylated copolymer. A typical copolymer is C 2-22 Ethoxylated and propoxylated block and / or random polymers of straight-chain or branched alcohols.

[0250] In various embodiments, the emulsifier may be a hybrid emulsifier. Typical anionic emulsifiers are, for example, alkylbenzene sulfonates such as dodecylbenzene sulfonates (e.g., Agnique® ABS 60 C or 65 C), dioctyl sulfosuccinate, or anionic polymers such as polyacrylates. Other suitable emulsifiers are zwitterionic surfactants. Zwitterionic surfactants are surface-active compounds that contain at least one quaternary ammonium group and at least one carboxyl group and one sulfonate group in their molecule. Particularly suitable zwitterionic surfactants are so-called betaines, such as N-alkyl-N,N-dimethylglycinate ammonium (e.g., cocoalkyldimethylglycinate ammonium), N-acylaminopropyl-N,N-dimethylglycinate ammonium (e.g., cocoamidepropyldimethylglycinate ammonium), and 2-alkyl-3-carboxymethyl-3-hydroxyethyl imidazoline (which contains 8 to 18 carbon atoms in the alkyl or acyl group), as well as cocoamideethylhydroxyethylcarboxymethylglycinate. Fatty acid amide derivatives known by the CTFA name of cocamidopropyl betaine are particularly preferred. Amphoteric surfactants are also suitable emulsifiers. Amphoteric surfactants are surface-active compounds, and their molecules contain C2... 8 / 18 In addition to the alkyl or acyl group, it contains at least one free amino group and at least one -COOH- or -SO3H- group and is capable of forming an inner salt. Examples of suitable amphoteric surfactants are N-alkylglycine, N-alkylpropionic acid, N-alkylaminobutyric acid, N-alkyliminodipropionic acid, N-hydroxyethyl-N-alkylamidopropylglycine, N-alkyltaurine, N-alkylsarcosine, 2-alkylaminopropionic acid, and alkylaminoacetic acid (which contain about 8 to 18 carbon atoms in the alkyl group). Particularly preferred amphoteric surfactants are N-cocoalkylaminopropionate, cocoylaminoethylaminopropionate, and C... 12 / 18 Acylsarcosine.

[0251] In a preferred embodiment, the emulsifier or surfactant is selected from nonionic or anionic surfactants and mixtures thereof, optionally castor oil ethoxylates, fatty acid alkoxylates, alcohol alkoxylates, alkylamine alkoxylates, polyether copolymers, sorbitol ethoxylates, aromatic alcohol alkoxylates, alkylbenzene sulfonates or (dioctyl) sulfosuccinates or mixtures thereof.

[0252] In various embodiments, at least one emulsifier or surfactant is castor oil ethoxylate or alkylbenzene sulfonate or a mixture thereof.

[0253] In addition to these essential components, formulations / mixtures may further contain adjuvants commonly used in agricultural chemical formulations. The choice of these adjuvants depends on the specific application, the type of formulation, or the active ingredient. Examples of suitable adjuvants include surfactants (such as solubilizers, protective colloids, wetting agents, and thickeners), retainers, wetting agents, spreading agents, absorption enhancers, penetrants, spray drift control agents, crystallization inhibitors, organic and inorganic thickeners, bactericides, antifreeze agents, defoamers, optionally colorants and binders (e.g., for seed treatment) or conventional adjuvants used in bait formulations (e.g., attractants, feedants, bittering substances).

[0254] In various embodiments, the composition comprises at least one urethane-based solvent according to formula (I) in an amount of 1 to 99 wt.-%, preferably 5 to 90 wt.-%, more preferably 10 to 70 wt.-%, even more preferably 20 to 70 wt.-% or 30 to 70 wt.-% (e.g., 35 to 65 wt.-%). In various embodiments, this amount may be about 45 wt.-%, about 48 wt.-%, about 50 wt.-%, about 55 wt.-%, about 60 wt.-%, or about 63 wt.-% relative to the total weight of the composition.

[0255] In various embodiments, the composition comprises at least one agrochemical active ingredient in an amount of 1 to 50 wt.-%, preferably 5 to 45 wt.-%, more preferably 10 to 40 wt.-%, or 15 to 35 wt.-%, such as about 15, about 18, about 20, about 22, about 25, about 28, about 30, or about 32 wt.-%, relative to the total weight of the composition.

[0256] In various embodiments, the composition comprises

[0257] a. At least one urethane-based solvent according to formula (I), in an amount of 1 to 99 wt.-%, preferably 5 to 90 wt.-%, more preferably 10 to 70 wt.-%, even more preferably 20 to 70 wt.-% or 30 to 70 wt.-% (e.g., 35 to 65 wt.-%). In various embodiments, this amount may be about 45 wt.-%, about 48 wt.-%, about 50 wt.-%, about 55 wt.-%, about 60 wt.-%, or about 63 wt.-%.

[0258] b. At least one agrochemical active ingredient, in an amount of 1 to 50 wt.-%, preferably 5 to 45 wt.-%, more preferably 10 to 40 wt.-% or 15 to 35 wt.-%, for example, in an amount of about 15, about 18, about 20, about 22, about 25, about 28, about 30 or about 32 wt.-%; and optionally,

[0259] c. At least one additional compound, preferably selected from cosolvents, surfactants, auxiliaries and / or emulsifiers and / or surfactants and / or auxiliaries, in an amount of 0 to 90 wt.-%, preferably 0.1 to 70 wt.-%, more preferably 1 to 50 wt.-%, for example 1 to 40 wt.-% or 1 to 30 wt.-%; and / or, optionally,

[0260] d. Water, preferably added to 100 wt.%;

[0261] Each is based on the total weight of the composition.

[0262] In the context of this invention, the phrase "add to 100 wt.-%" means that the composition can be made up with water to achieve a total volume of 100 wt.-%

[0263] Preferably, the composition according to the invention is an agricultural chemical composition.

[0264] In the context of this invention, "agricultural chemicals" or "agricultural chemical compositions" preferably refers to chemical products used in industrial agriculture.

[0265] In a second aspect, the present invention relates to the use of carbamates according to formula (I) in agrochemicals as solvents or dispersants for at least one active ingredient, preferably an agrochemical active ingredient.

[0266] Preferably, the urethane ester is a urethane-based solvent according to formula (I) as described above. Preferably, the urethane ester is an aprotic solvent.

[0267] The present invention also relates to the use of carbamates according to formula (I) as solvents in agrochemical formulations (such as concentrates, emulsion concentrates, suspension concentrates or dispersion concentrates, especially emulsion concentrates).

[0268] In various embodiments, the carbamate preferably improves the stability of the concentrate or formulation (such as an emulsion concentrate or emulsion formulation) compared to other solvents not according to the invention (such as alkyl esters, including 2-ethylhexyl acetate). In various embodiments, the carbamate according to the invention is (hydrophobic) N,N-dimethylcarbamate n-butyl ester.

[0269] The compositions disclosed herein are generally used to control harmful organisms in plants, such as harmful fungi or insects. Such uses typically include applying the compositions of the invention to at least a portion of the plant, to the soil in which they grow, or to their seeds. Application can be carried out by any suitable and generally known means, such as spraying.

[0270] The same methods for using the compositions described herein to control harmful organisms (e.g., harmful fungi or insects) in plants are also intended to be covered by this invention. Such methods include applying the compositions of this invention to said plants, to the soil in which they grow, or to their seeds, for example by spraying.

[0271] In cases where the composition of the present invention is a concentrate, the use or method may further include the step of diluting the concentrate to a desired concentration using a suitable liquid medium (e.g., water). The concentrate may be, but is not limited to, an emulsion concentrate, a suspension concentrate, or a dispersion concentrate.

[0272] As used herein, the term "plant" is preferably understood to mean plants of economic importance and / or artificially cultivated plants. In some embodiments, the term may also be understood to mean plants that are not of economic importance or do not have significant economic importance. Plants are preferably selected from agricultural plants, afforestation plants, and horticultural (including ornamental) plants. The term also includes genetically modified plants.

[0273] As used herein, the term "plant" further includes all parts of a plant, such as germinating seeds, seedlings, propagules, herbaceous plants, and established woody plants, including all subsurface parts (such as roots) and above-ground parts.

[0274] In one embodiment, the plant is an agricultural plant. An "agricultural plant" is a plant whose parts (e.g., seeds) or all of which are harvested or cultivated on a commercial scale or used as a significant source of feed, food, fiber (e.g., cotton, flax), combustibles (e.g., wood, bioethanol, biodiesel, biomass), or other compounds. Preferred agricultural plants include, for example, cereals such as wheat, rye, barley, triticale, oats, corn, sorghum, or rice; sugar beets, such as sugar beets or feed beets; fruits such as pome fruits, drupes, or berries such as apples, pears, plums, peaches, apricots, cherries, strawberries, raspberries, blackberries, or gooseberries; legumes such as lentils, peas, alfalfa, or soybeans; oilseed plants such as rapeseed, oilseed rape, canola, flaxseed, mustard, olives, sunflowers, coconuts, cocoa beans, castor oil plants, oil palms, peanuts, or soybeans; and cucurbits such as… Pumpkin, cucumber, or melon; fiber plants such as cotton, flax, hemp, or jute; citrus fruits such as oranges, lemons, grapefruits, or tangerines; vegetables such as spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, melons, or peppers; laurel plants such as avocados, cinnamon, or camphor; energy and raw material plants such as corn, soybeans, canola, sugarcane, or oil palm; tobacco; nuts; coffee; tea; bananas; grapevines (table grapes and grape juice vines); hops; turf; natural rubber plants.

[0275] In another embodiment, the plant is a horticultural plant. The term "horticultural plant" should be understood as a plant commonly used in horticulture, such as in the cultivation of ornamental plants, vegetables, and / or fruits. Examples of ornamental plants are lawns, geraniums, geraniums, petunias, begonias, and lantern begonias. Examples of vegetables are potatoes, tomatoes, peppers, melons, cucumbers, cantaloupes, watermelons, garlic, onions, carrots, cabbage, green beans, peas, and lettuce, with a preference for tomatoes, onions, peas, and lettuce. Examples of fruits are apples, pears, cherries, strawberries, citrus fruits, peaches, apricots, and blueberries.

[0276] In another embodiment, the plant is an ornamental plant. "Ornamental plant" refers to plants commonly used in horticulture, such as in parks, gardens, and on balconies. Examples include lawns, geraniums, geraniums, petunias, begonias, and lantern begonias.

[0277] In another embodiment of the invention, the plant is an afforestation plant. The term "afforestation plant" should be understood as trees, and more specifically, for trees in reforestation or industrial planting. Industrial planting is commonly used for the commercial production of forest products such as timber, pulp, paper, rubber trees, Christmas trees, or saplings for horticultural purposes. Examples of afforestation plants are conifers, such as pine, especially species of the genus *Pinus*, fir and spruce, eucalyptus, tropical trees, such as teak, rubber trees, oil palm, willow (*Salix*), especially species of the genus *Salix*, poplar (*Populus trilobus*), especially species of the genus *Populus*, beech, especially species of the genus *Betula*, birch, oil palm, and oak.

[0278] The term "genetically modified plant" should be understood as a plant whose genetic material has been modified using recombinant DNA technology in a way that would not be easily obtained naturally through hybridization, mutation, or natural recombination. Typically, one or more genes are integrated into the genetic material of a genetically modified plant to improve certain plant characteristics. Such gene modifications also include, but are not limited to, targeted post-translational modifications of proteins, oligopeptides, or polypeptides, such as through glycosylation or polymer additions like isoprenelation, acetylation, or farnesylation of the moiety or PEGylation.

[0279] It also covers plants that have been modified through breeding, mutagenesis, or genetic engineering, for example, to tolerate the application of specific classes of herbicides through conventional breeding or genetic engineering methods. These herbicides include plant growth regulator herbicides such as dicamba or 2,4-D; bleaching herbicides such as hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors or phytoene desaturase (PDS) inhibitors; acetyllactone synthase (ALS) inhibitors such as sulfonylureas or imidazolinones; enolpyruvylshikimate-3-phosphate synthase (EPSPS) inhibitors such as glyphosate; glutamine synthase (GS) inhibitors such as glufosinate; protoporphyrinogen-IX oxidase inhibitors; lipid biosynthesis inhibitors such as acetyl-CoA carboxylase (ACCase) inhibitors; or oxynil (i.e., bromobenzonitrile or iodobenzonitrile) herbicides. In addition, plants have developed resistance to multiple classes of herbicides through repeated genetic modifications, such as resistance to both glyphosate and glufosinate, or resistance to both glyphosate and herbicides from another class, such as ALS inhibitors, HPPD inhibitors, auxin inhibitors, or ACCase inhibitors. These herbicide tolerance techniques are described, for example, in Pest Managem. Sci. 61, 2005, 246; 61, 2005, 258; 61, 2005, 277; 61, 2005, 269; 61, 2005, 286; 64, 2008, 326; 64, 2008, 332; Weed Sci. 57, 2009, 108; Austral. J. Agricult. Res. 58, 2007, 708; Science 316, 2007, 1185; and the references cited therein. Several cultivated plants have been made herbicide tolerant through conventional breeding methods (mutation), such as Clearfield. ® Summer rapeseed (canola rapeseed, BASF SE, Germany) is tolerant to imidazolinones (e.g., imazamox), or ExpressSun. ® Sunflowers (DuPont, Inc.) are tolerant to sulfonylureas (e.g., bensulfuron-methyl). Genetic engineering methods have been used to make cultivated plants such as soybeans, cotton, corn, sugar beets, and rapeseed tolerant to herbicides such as glyphosate and glufosinate, some of which are marketed under the trade name RoundupReady. ® (Glyphosate tolerance, Monsanto, USA) Cultivance ® (Imidazolinone tolerance, BASF Europe, Germany) and LibertyLink ®(Glufosinate tolerance, Bayer CropScience, Germany) is commercially available. Methods for producing such genetically modified plants are generally known to those skilled in the art and are described, for example, in the aforementioned publications.

[0280] Furthermore, this also covers plants that can synthesize one or more proteins using recombinant DNA technology to enhance their resistance or tolerance to bacterial, viral, or fungal pathogens. Examples of such proteins are so-called "pathogenesis-associated proteins" (PR proteins, see, for example, EP-A 392 225), plant disease resistance genes (e.g., potato varieties expressing resistance genes that act against Phytophthora infestans from the Mexican wild potato *Solanum bulbocastanum*), or T4-lysozymes (e.g., potato varieties capable of synthesizing these proteins with enhanced resistance to bacteria such as *Erwinia amylvora*). Methods for producing such genetically modified plants are generally known to those skilled in the art and are described, for example, in the aforementioned publications.

[0281] In addition, it also covers plants that are able to synthesize one or more proteins to improve plant productivity (e.g., biomass production, grain yield, starch content, oil content, or protein content) through the use of recombinant DNA technology, tolerance to drought, salinity, or other growth-limiting environmental factors, or tolerance to pests and pathogens such as fungi, bacteria, or viruses.

[0282] Furthermore, it also covers plants that have been modified or have new contents of substances through the use of recombinant DNA technology to improve human or animal nutrition, such as oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e.g., Nexera). ® Rapeseed, Dow Agro Sciences, Canada.

[0283] Furthermore, it also covers plants that have undergone altered or novel processes using recombinant DNA technology to particularly improve the production of raw materials, such as potatoes that produce increased amounts of amylopectin (e.g., Amflora). ® Potatoes, BASF Europe, Germany.

[0284] In further embodiments, the present invention relates to compounds 3-methoxypropyl-N,N-dimethylcarbamate and / or 2-acetylpropyl-N,N-dimethylcarbamate and methods for their synthesis. The structures of these two compounds are also shown in the table above as compounds 5 and 6, and they are used in examples as compounds F and H.

[0285] All embodiments and examples of the compositions described herein are applicable to the uses and methods disclosed herein, and vice versa.

[0286] The invention is further illustrated by the following examples. Example

[0287] Synthetic procedures for generating carbamate compounds

[0288] The following general procedures are used to produce the compounds tested in the following examples. These methods are generally known to those skilled in the art, and the corresponding methodological details can therefore be determined by those skilled in the art by means of conventional methods or their common general knowledge.

[0289] 1.) Phosgene-based (used in compounds A, B, C, D, E, F, and N)

[0290] a. Add a monohydric alcohol to phosgene to produce chloroformate.

[0291] b. Add dimethylamine to chloroformate to produce alkyl dimethyl carbamate.

[0292] Exemplary reaction scheme:

[0293]

[0294] 2.) Carbonate-based (see EP 2 327 302 A1; for the formation of compounds G, H, L and M)

[0295] a. Adding dimethylamine (compounds L and M) to cyclic carbonates (e.g., propylene carbonate); and

[0296] b. Optionally, the terminal hydroxyl group can be converted to an ester (e.g., by reaction with acetic anhydride or an acid) (compounds G and H)

[0297] Exemplary reaction scheme:

[0298]

[0299] Determination of maximum solubility of biocides

[0300] The maximum solubility of the biocidal agent in various solvents was determined at 21°C. In this study, a small amount of the active ingredient was added to 10 g of solvent in a 25 mL beaker with stirring using a magnetic stir bar. The dosage of the active ingredient was added to the solvent until no further dissolution was achieved, with stirring time of up to 2 hours between additions to allow for dissolution. The solubility was calculated according to the following equation:

[0301]

[0302] Determination of the solubility of solvent in water:

[0303] The water solubility of the solvent was determined according to a method based on CIPAC MT157.1 and OECD 105 by evaluating the amount of undissolved solvent in water after vigorous mixing and settling. In this study, different amounts of solvent and water were mixed in graduated cylinders or separatory funnels with glass stoppers under vigorous shaking, followed by settling for at least 30 minutes to allow for separation. For example, if undissolved solvent was observed after thoroughly mixing 0.1 g of solvent in 100 mL of water, the solvent had a water solubility equal to or less than 0.1% (≤1 g / L). This method can be repeated with different amounts of solvent and water to allow for the determination of the solvent's water solubility.

[0304] CIPAC D Water: Standard Water prepared in the laboratory using the standard formulation "MT 18.1.4" published by CIPAC. This water has a hardness of 342 ppm and a Ca:Mg ion mixture of 4:1 at pH 6-7.

[0305] Emulsion stability at room temperature (21°C) at 5% concentration

[0306] The dispersibility of an emulsion is tested by an effect known as blooming.

[0307] The emulsion was evaluated based on its spontaneous emulsification (referred to in the art as "self-emulsification") upon the addition of the concentrate to water, using a visual evaluation given on a scale of 1 to 5, where 1) Excellent, "emulsion cloud" does not settle to the bottom of the graduated cylinder; 2) Good, "emulsion cloud" but settles to the bottom of the graduated cylinder; 3) Okay, "poor emulsion cloud", larger droplets; 4) Poor, "no emulsion cloud", small "particles" are observed; 5) Very poor, no emulsion, oil and aqueous phases separate immediately.

[0308] In the following examples, emulsifiable concentrates were prepared, and the resulting 5% w / w emulsions were evaluated for various water hardnesses at 21°C after 24 hours. Emulsion stability was determined by measuring changes in cream or sediment over time.

[0309] To measure emulsion stability, 5.0 mL of the emulsifiable concentrate was diluted in 95.0 mL of CIPAC D water in a 100 mL measuring cylinder. The stability of the resulting oil-in-water emulsion was evaluated after 1, 2, 4, and 24 hours. A highly stable emulsion did not form a cream or sediment after 24 hours, or had less than 1.5 mL of cream or sediment, and could be easily reemulsified without forming a cream or sediment after standing for 24 hours, wherein such reemulsified emulsions were evaluated 30 minutes after reemulsification. Both initial emulsification and reemulsification were achieved by gently inverting the emulsion 10 times. In the table below, Y (i.e., yes) indicates that at most 1.5 mL of cream or sediment was observed after 24 hours, while N (i.e., no) indicates that more than 1.5 mL of cream or sediment was observed after 24 hours.

[0310] Example 1: Solubility of active ingredients

[0311] The solubility of the active ingredients in various active substances was determined using the method described above. The results are shown in Table 2.

[0312] Table 2: Solubility of active ingredients, in w / w %

[0313]

[0314] A: Ethyl-N,N-dimethylcarbamate (CAS: 687-48-9); B: n-propyl-N,N-dimethylcarbamate (CAS: 6154-16-1).

[0315] C: n-Butyl-N,N-dimethylcarbamate (CAS: 7304-97-4); D: 2-Methoxyethyl-N,N-dimethylcarbamate (DMAMEC) (CAS: 50883-78-8);

[0316] E: Butoxyethyl-N,N-dimethylcarbamate (CAS: 98957-13-2); F: 3-Methoxypropyl-N,N-dimethylcarbamate;

[0317] G: 2-Acetylethyl-N,N-dimethylcarbamate (CAS: 98436-11-4), H: 2-Acetylpropyl-N,N-dimethylcarbamate;

[0318] I: Propylene carbonate; J: Propylene glycol; K: Dipropylene glycol monoethyl ether;

[0319] L: 2-Hydroxyethyl-N,N-dimethylcarbamate (CAS: 3694-86-8); M: 2-Hydroxypropyl-N,N-dimethylcarbamate (CAS: 37499-18-6)

[0320] Hydroxydimethylcarbamates (L and M) exhibit lower solubility than hydroxyl-terminated molecules (A to H). Furthermore, hydroxyl-terminated molecules (A to H) show increased solubility compared to market standards (I, J, and K). This is in Figure 1 This was confirmed in studies showing that water-soluble 2-methoxyethyl-N,N-dimethylcarbamate (compound D) and 2-acetylethyl-N,N-dimethylcarbamate (G) exhibited better solution properties than the structure-related uncapped analog 2-hydroxyethyl-N,N-dimethylcarbamate (L).

[0321] Example 2: Water solubility

[0322] The water solubility of various solvents was determined using the method described above. The results are shown in Table 3.

[0323] Table 3: Comparison of solvent properties based on urethane esters.

[0324]

[0325] A: Ethyl-N,N-dimethylcarbamate (CAS: 687-48-9); B: n-propyl-N,N-dimethylcarbamate (CAS: 6154-16-1); C: n-butyl-N,N-dimethylcarbamate (CAS: 7304-97-4); D: 2-methoxyethyl-N,N-dimethylcarbamate (DMAMEC) (CAS: 50883-78-8); G: 2-acetylethyl-N,N-dimethylcarbamate (CAS: 98436-11-4); I: propylene carbonate; J: propylene glycol (CAS 57-55-6); K: dipropylene glycol monoethyl ether (34590-94-8); N: 2-ethylhexyl-N,N-dimethylcarbamate (CAS: 20708-22-9); O: dimethyldecylamide (Agnique AMD) 10) (CAS: 14433-76-2).

[0326] exist Figure 2 In this study, hydrophobic n-butyl-N,N-dimethylcarbamate (CAS: 7304-97-4) (compound C) was shown to have similar solution properties to dimethyldecylamide (Agnique AMD 10) (compound O). The solubility of azoxystrobin, ethoxyflufenoxam, difenoconazole, oxadiazon, and fluthiamethoxam increased. The water solubility of n-butyl-N,N-dimethylcarbamate was 0.4%, while that of n-propyl-N,N-dimethylcarbamate was 1.7%.

[0327] The excellent solubility and low solubility (< 1 w / w %) of n-butyl-N,N-dimethylcarbamate (compound C) enable the formulation of stable emulsion concentrates. Furthermore, the low solubility of n-butyl-N,N-dimethylcarbamate (compound C) allows for the production of stable emulsions from emulsifiable concentrates under standard conditions when mixed with water (see Table 4).

[0328] Example 3: Emulsion (concentrate) formulations

[0329] An emulsion (concentrate) was formed as described above and evaluated. The results are shown in Table 4.

[0330] Table 4: Emulsion concentrates and emulsion formulations containing n-butyl-N,N-dimethylcarbamate (compound C).

[0331]

[0332] The emulsion was tested in water at 5 wt.-%. “Good stability” means that the emulsion / sediment level after 24 h is ≤1.5 mL (S = sediment, C = cream).

Claims

1. A composition comprising a. At least one urethane-based solvent according to formula (I) (R 1 R 2 )N-C(=O)O-R 3 (I) in R 1 and R 2 Each is independently a straight-chain or branched C1-C4 alkyl group; and R 3 Is it a straight or branched C1-C? 10 Alkyl, R 4 -OC(=O)-R 5 Or R 4 -OR 5 , R 4 Is it a straight or branched C1-C? 10 -alkylene; and R 5 It is a straight-chain or branched C1-C8 alkyl group, preferably a straight-chain or branched C1-C4 alkyl group; The premise is that if R 3 Is it a straight or branched C1-C? 10 Alkyl group, then R 1 and R 2 Each of the following is independently methyl or ethyl, preferably methyl; and b. At least one agrochemical active ingredient, wherein the at least one agrochemical active ingredient is not a carbamate-based solvent according to formula (I).

2. The composition according to claim 1, wherein, R 1 and R 2 They are the same and preferably methyl.

3. The composition according to claim 1 or 2, wherein, If R 3 It is R 4 -OC(=O)-R 5 Or R 4 -OR 5 Then R 4 It is (CH2) m (R)CH-(CH2) n Or (CH2) o -CH(R), wherein m, n and o are independent integers from 1 to 8, preferably from 1 to 4, and R is a C1-C4 alkyl, preferably methyl or ethyl.

4. The composition according to any one of claims 1 to 3, wherein, (1) R 3 It is R 4 -OR 5 , where R 4 It is CH2-CH2, CH2-CH2-CH2, CH2-CH(R) or CH(R)-CH2, wherein R is methyl or ethyl, preferably methyl, and / or R 5 It is methyl, ethyl, propyl, or butyl; or (2) R 3 It is R 4 -OC(=O)-R 5 , where R 4 It is CH2-CH2, CH2-CH2-CH2 or CH2-CH(R), where R is methyl or ethyl, preferably methyl, and / or R 5 It is methyl, ethyl, propyl, or butyl.

5. The composition according to any one of claims 1 to 4, wherein, R 1 and R 2 It is methyl, R 3 It is R 4 -OR 5 R 4 It is CH2-CH2, CH2-CH2-CH2, CH2-CH(CH3) or CH(CH3)-CH2, and R 5 It is methyl or butyl.

6. The composition according to any one of claims 1 to 4, wherein, R 1 and R 2 It is methyl, R 3 It is R 4 -OC(=O)-R 5 R 4 It is CH2-CH2 or CH2-CH(CH3), and R 5 It is a methyl group.

7. The composition according to claim 1 or 2, wherein, R 3 It is a straight-chain or branched C2-C8 alkyl group, preferably ethyl, propyl, butyl or 2-ethylhexyl, more preferably ethyl, n-propyl or n-butyl.

8. The composition according to any one of claims 1 to 7, wherein, The carbamate-based solvent is selected from at least one compound from the following list: 。 9. The composition according to any one of claims 1 to 8, wherein, The at least one agricultural chemical active substance is selected from the group consisting of herbicides, fungicides, insecticides, and combinations thereof.

10. The composition according to any one of claims 1 to 9, wherein, The at least one agrochemical active ingredient is selected from the group consisting of: azoxystrobin, tebuconazole, ethoxyflufenoxam, oxadiazon, cyclohexidine, prothioconazole, fluthiamethoxam, imidacloprid, difenoconazole, pyraclostrobin, and combinations thereof, preferably azoxystrobin, prothioconazole, ethoxyflufenoxam, difenoconazole, tebuconazole, and combinations thereof.

11. The composition according to any one of claims 1 to 10, wherein, The composition comprises at least one additional compound selected from the group consisting of: cosolvents, dispersants, auxiliaries, surfactants, thickeners, wetting agents, antioxidants, colorants, fragrances, defoamers, anti-caking agents, emulsifiers, and mixtures thereof.

12. The composition according to claim 11, wherein, - The at least one cosolvent is selected from fatty acid methyl esters, aromatic hydrocarbons, 2-ethylhexanol esters, dimethyl fatty amides, dimethyl alkyl amides, fatty alcohols, glycols, alkyl esters, lactates, alkylpyrrolidones, paraffin mineral oils, vegetable oils, lactones, carbonates, urethanes, alkylamides, ketones, phosphate esters, aldehydes, ethers, acetals, and mixtures thereof, which are different from urethane-based solvents having formula (I); and / or - The emulsifier is selected from nonionic or anionic surfactants and mixtures thereof, optionally... Castor oil ethoxylates, fatty acid alkoxylates, alcohol alkoxylates, alkylamine alkoxylates, polyether copolymers, sorbitol ethoxylates, aromatic alcohol alkoxylates, alkylbenzene sulfonates or (dioctyl) sulfosuccinates.

13. The composition according to any one of claims 1 to 12, wherein, The composition contains a. At least one urethane-based solvent according to formula (I), in an amount of 1 to 99 wt.-%, preferably 5 to 90 wt.-%, more preferably 10 to 70 wt.-%, such as about 45 wt.-%, about 50 wt.-%, about 55 wt.-%, about 60 wt.-%, or about 63 wt.-%; b. At least one agrochemical active ingredient, in an amount of 1 to 50 wt.-%, preferably 10 to 40 wt.-%, more preferably 15 to 30 wt.-%, such as about 20 wt.-% or about 25 wt.-%; and, optionally, c. At least one additional compound, preferably selected from cosolvents, surfactants, auxiliaries and / or emulsifiers, in an amount of 0 to 90 wt.-%, preferably 0.1 to 70 wt.-%, more preferably 1 to 50 wt.-%; and / or d. Water, preferably added to 100 wt.%; Each is based on the total weight of the composition.

14. The composition according to any one of claims 1 to 13, wherein, This composition is an agricultural chemical composition.

15. According to the uses of the carbamate of formula (I), (R 1 R 2 )N-C(=O)O-R 3 (I) in R 1 and R 2 Each is independently a straight-chain or branched C1-C4 alkyl group; and R 3 Is it a straight or branched C1-C? 10 Alkyl, R 4 -OC(=O)-R 5 Or R 4 -OR 5 , R 4 Is it a straight or branched C1-C? 10 -alkylene; and R 5 It is a straight-chain or branched C1-C8 alkyl group, preferably a straight-chain or branched C1-C4 alkyl group; The premise is that if R 3 Is it a straight or branched C1-C? 10 Alkyl group, then R 1 and R 2 Each of the components is independently a C1-C3 alkyl group, preferably methyl or ethyl, with methyl being the most preferred. This application is (1) As a solvent or dispersant for at least one agricultural chemical active ingredient, wherein the at least one agricultural chemical active ingredient is not a carbamate according to formula (I); or (2) Used as a solvent in agricultural chemical formulations, preferably for improving stability compared to other solvents.

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