Adjuvants

Abstract

The present invention relates to compositions comprising certain (biological performance improving) alcohol alkoxylate adjuvants and agrochemicals; and to the use of these adjuvants for improving the biological properties of agrochemicals.

Description

[0001] This application is a divisional application of Chinese invention patent application No. 201780077421.6 entitled "Adjuvant", which was filed on December 11, 2017, and has a priority date of December 15, 2016.

[0002] This invention relates to compositions comprising certain alcohol alkoxylate adjuvants (for improving biological performance) and agrochemicals; and to the use of these adjuvants for improving the biological performance of agrochemicals.

[0003] It is known that adjuvants can improve the biological properties of agrochemicals, and certain alcohol alkoxylates can act as such adjuvants. This invention relates to a class of alcohol alkoxylates that were previously unknown as adjuvants and unexpectedly perform better than other known adjuvants.

[0004] The adjuvant of this invention has the structure RO-[R1O]. m -[R2O] n -H where R is C 16 To C 18 (C) 16-18 That is, from C 16 To C 18 The adjuvant is a straight-chain or branched alkyl or alkenyl group, where R1 is isopropyl, R2 is ethyl, m is from 1 to 15, and n is from 1 to 25. This means that each R1O represents a propylene oxide [PO] unit, and each R2O represents an ethylene oxide [EO] unit. This adjuvant can be present in formulations along with agrochemicals.

[0005] Therefore, in one aspect, the present invention provides a composition comprising:

[0006] (i) Compounds having formula (I)

[0007] RO-[PO] m -[EO] n -H (I)

[0008] Where R is C 16-18 Straight-chain or branched alkyl or alkenyl groups, where m is from 1 to 15 and n is from 1 to 25; and

[0009] (ii) Agricultural chemicals.

[0010] Appropriately, the carbon chain of R is such that it is C 16 and C 18 Blends.

[0011] In one respect, R is preferably C 16 To C 18 Straight-chain alkyl; more preferably, it is C16 and C 18 Blends.

[0012] In another respect, R is preferably oleylene.

[0013] m is preferably from 2 to 10; more preferably from 4 to 9; and even more preferably from 4 to 6.

[0014] n is preferably from 2 to 20; more preferably from 4 to 15; and even more preferably from 4 to 12.

[0015] Preferably, m is the average number of PO cells.

[0016] Preferably, n is the average number of EO units.

[0017] The terms “agricultural chemicals” and “agricultural chemical active ingredients” are used interchangeably herein and include herbicides, insecticides, nematicides, molluscicides, fungicides, plant growth regulators, and safety agents; preferably herbicides, insecticides, and fungicides; and more preferably fungicides and herbicides.

[0018] Agricultural chemicals selected from those given below, or salts of such agricultural chemicals, are applicable to this invention.

[0019] Suitable herbicides include: cyclopyrid, flupyrfluthrin, mesotrione, flusulfanilamide, styraclostrobin, chlorpyrifos, amitraz, propargite, pyrimethanil, chlorpyrifos, tetrachloronitrobenzene, methyl thiophanate, dicofol M, 2,4-D, MCPA, 2-methyl-4-chloropropionic acid, clodinafop-propargyl, cyhalofop-butyl, quizalofop-p-ethyl, haloxyfop-p-ethyl, quizalofop-p-ethyl, indole-3-ylacetic acid, 1-naphthacetic acid, isoxaflutole, cyhalofop-p-ethyl, dimethyl dichlorvos, benomyl, furazolidone, dicofol, dichlorvos, imazolidone, fluzolon, fenfluramide, betaine, acetochlor, metolachlor, succinate, thiamethoxam, quizalofop-p-ethyl, clethodim, cyclodim, clethodim, dexamethasone, pendimethalin, terbufloxacin, methyl carboxylic acid Herbicides including oxyfluorfen, flufenoxuron, quizalofop-P-ethyl, S-metolachlor, glyphosate, glufosinate, paraquat, diquat, ethoxysulfuron, bromonazine, iodobenzonitrile, methyl imidacloprid, metribuzin, metribuzin, imidacloprid, methamidophos, propyzamide, flumethrin, chlorpyrifos, amodosulfuron, and chlorsulfuron. Nicosulfuron, sulfadiazine, fensulfuron, fensulfuron-methyl, chlorpyrifos, chlorpyrifos, clethodim, atrazine, simazine, cyanazine, atrazine, pyrazosulfuron, terbufos, terbufos, sulfadiazine, isoproturon, linuron, felsulfuron, chlorpyrifos, methoxyfenozide, iodosulfuron-methyl, mesosulfuron-methyl, pyrfluthrin, fluthiamethoxam, flusulfanilamide, chlorpyrifos, chlorpyrifos, XDE-848 Rinskor, and fluchloropyridine ester.

[0020] Suitable fungicides include: pyraclostrobin, dimethomorph, azoxystrobin, oxadiazon, fenpyroxen, metalaxyl, oxadixyl, fenoxystrobin, azoxystrobin, cyprodanil, carbendazim, thiabendazole, dimethomorph, vinclozolin, iprodione, dithiocarbamate, imazalil, prochloraz, fluquinazole, flutriafol, fenbendazole, azaconazole, bifenthrin, furazolidone, ciprofloxacin, difenoconazole, hexaconazole, paclobutrazol, propiconazole, tebuconazole, triadimefon, and sterilizing agents. Tridecimorphazole, thiram, tridecimorph, benzyl benzoate, mancozeb, mancozeb, chlorothalonil, thiram, zinc thiram, captan, chlorpyrifos, fluazinam, fluamide, metalaxyl, ethirimol sulfonate, ethamythromycin, azoxystrobin, fluazinam, oxadiazon, fenoxystrobin, prothioconazole, fluazinam hydroxylamine, bifenpyraclostrobin, fluazinam, prothioconazole, azoxystrobin ester, chlorfluazon, benzo[a]fluoroquinolones, and xemium.

[0021] Suitable insecticides include: thiamethoxam, imidacloprid, acetamiprid, thiamethoxam, dinotefuran, acetamiprid, fipronil, abamectin, emamectin, heptamethrin, emamectin benzoate, oxadiazon, carbaryl, fenoxycarb, isoprocarb, pirimicarb, propoxur, methomyl, sulfadiazine, chlorpromazine, endosulfan, heptachlor, tebufenozide, chlorfenapyr, ethoxysulfuron, methyl pyrimiphos, aldicarb, methomyl, cypermethrin, bio-allethrin, deltamethrin, lambda-cyhalothrin, deltamethrin, cypermethrin, fenvalerate, propargite, permethrin, fenpyroxenon, fenvalerate, nematicide, flupyrflufenoxam, fluoxastrobin, inscalis, rynaxypyr, brofenoxam, flonicamid, and spinosad.

[0022] Suitable plant growth regulators include paclobutrazol, ethyl anti-loosening ester, and 1-methylcyclopropene.

[0023] Suitable safeners include glyphosate, quinacrine, glyphosate nitrile, dichloropropeneamine, ethyl glyphosate, glyphosate nitrile, glyphosate nitrile, fluroxypyr, pyrazosulfuron, MG-191, naphthalenecarboxylic anhydride, and glyphosate nitrile.

[0024] Suitablely, the agrochemicals are selected from flupyradifon, mesotrione, cyclopyralid, flusulfanilamide, styraclostrobin, diflubenzuron, amitraz, propargite, pyrimethanil, clodinafop-methyl, tetrachloronitrobenzene, methyl parathion, dicofol M, 2,4-D, MCPA, 2-methyl-4-chloropropionic acid, clodinafop-propargyl, cyhalofop-butyl, quizalofop-p-ethyl, pyrifluquinazon, quizalofop-p-ethyl, indole-3-ylacetic acid, 1-naphthaleneacetic acid, isoxaflutole, cyhalofop-p-ethyl, dimethyl diflubenzuron, benomyl, furazolidone, dicofol, diflubenzuron, imazolidone, fluzolon, fenfluramide, betaine, acetochlor, metolachlor, propachlor, thifensulfuron-methyl, quizalofop-p-ethyl, butyrazanol, clethodim, cyclohexane. , ... Cyprodanil, carbendazim, thiabendazole, dimethomorph, vinclozolin, iprodione, dithiocarbamate, imazalil, propiconazole, fluquinazole, flutriafol, fenbendazole, azaconazole, bifenthrin, furazolidone, cyclophosphamide, difenoconazole, hexaconazole, paclobutrazol, propiconazole, tebuconazole, triadimefon, tebuconazole, butylmorpholine, tridemorpholine, benzyl benzoate, mancozeb, mancozeb, chlorothalonil, thiram, zinc thiram, captan, captan, fentanyl, fluazinam, fluoxastrobin, metalaxyl, ethirimol sulfonate, ethamazol, azoxystrobin, fluazinam, fluazinam, oxadiazon, fenoxystrobin, prothioconazole, thiamethoxam, imidacloprid, acetamiprid Thiamethoxam, fipronil, acetamiprid, fipronil, abamectin, emamectin, oxadiazon, carbaryl, phenoxycarb, isoprocarb, pirimicarb, propoxur, methomyl, sulfadiazine, chlorpromazine, endosulfan, heptachlor, tebufenozide, chlorfenapyr, ethoxysulfuron, methyl pyrimiphos, aldicarb, methomyl, cypermethrin, bio-allethrin, deltamethrin, lambda-cyhalothrin, deltamethrin, cypermethrin, fenvalerate, cypermethrin, permethrin, deltamethrin, paclobutrazol, 1-methylcyclopropene, chlorpyrifos, chlorpyrifos, dichloropropeneamine, ethyl chlorpyrifos, chlorpyrifos, chlorpyrifos, fluroxypyr, pyrazosulfuron, MG-191, naphthalenecarboxylic anhydride, and chlorpyrifos.

[0025] Preferred active ingredients for agrochemicals are selected from flusulfanilamide (appropriately as a sodium salt), mesotrione, nicosulfuron, cyclopyridaben, pyraclostrobin, flutriafol, benzovindiflubenzuron, and broflanilide.

[0026] More preferably, the agrochemical is flusulfanilamide (appropriately as a sodium salt), mesotrione, nicosulfuron, or cyclophosphamide.

[0027] Different editions of the Pesticide Manual (particularly the 14th and 15th editions) also disclose details of agrochemicals, any of which may be suitably used in this invention.

[0028] Suitable, the compositions of the present invention may include one or more of the agrochemicals described above.

[0029] Generally, any agrochemical active ingredient will be present at a concentration from about 0.000001% to about 90% w / w, preferably from about 0.001% to about 90% w / w. The agrochemical compositions of the present invention can be in the form of ready-to-use formulations or in the form of concentrates suitable for further dilution by the end user, and the concentrations of the agrochemical and the compounds having formula (I) will be adjusted accordingly. When in concentrated form, the compositions of the present invention typically contain from 5% to 90% w / w, more preferably from 5% to 75% w / w, and even more preferably from 10% to 50% w / w of the total composition of the agrochemical. The ready-to-use compositions of the present invention will typically contain from 0.000001% to 1% w / w, more preferably from 0.000001% to 0.5% w / w, and even more preferably from 0.001% to 0.1% w / w of the total composition of the agrochemical.

[0030] Typically, compounds having formula (I) will have a concentration of from about 0.0005% to about 90% w / w, preferably from about 0.01% to about 90% w / w, of the total composition. When in concentrated form, the compositions of the present invention typically contain compounds having formula (I) of from 1% to 80% w / w, preferably from 5% to 60% w / w, more preferably from 5% w / w to 40% w / w, and even more preferably from 5% w / w to 20% w / w of the total composition. The ready-to-use compositions of the present invention typically contain compounds having formula (I) of from about 0.0005% to about 2% w / w, more preferably from about 0.01% to about 1% w / w, and even more preferably from 0.05% w / w to 0.5% w / w of the total composition. If, due to various values ​​of m and n, a particular individual compound having formula (I) exists together with blends of other compounds having formula (I), then these concentration ranges for that individual compound can be changed such that the lower limit is reduced by a factor of 10 and the upper limit by a factor of 2.

[0031] The compositions of the present invention may involve concentrates designed for addition to a farmer’s water spray can, or they may be applied directly without further dilution.

[0032] Preferably, the composition is selected from SC (suspension concentrate); SL ​​(soluble liquid); EC (emulsifiable concentrate); DC (dispersible concentrate); WG (water-dispersible granules); SG (soluble granules); EW (aqueous emulsion); SE (suspension emulsion); CS (capsule suspension); and OD (oil dispersion).

[0033] Furthermore, the adjuvant systems described herein can be designed for addition to formulations of agrochemicals (e.g., by mixing with water in a farmer's spray can).

[0034] Therefore, in another aspect, the present invention relates to the use of compounds having formula (I) for improving the biological properties of agrochemicals.

[0035] The compositions of the present invention may include other components well known to those skilled in the art, such as dispersants, surfactants, emulsifiers, solvents, polymers, defoamers, antimicrobial agents, colorants, and fragrances. Standard formulation disclosures disclose such formulation components suitable for use with the present invention (e.g., *Chemistry and Technology of Agrochemical Formulations*, edited by Alan Knowles, published by Kluwer Academic Publishers, Netherlands, 1998; and *Adjuvants and Additives*: 2006, edited by Alan Knowles, Agrow Report DS256, published by Informa UK Ltd, December 2006). These compositions may also contain other components for improving formulation compatibility; for example, water-soluble growth promoters and viscosity reducers, as discussed in WO 12052545, which are suitable for use with the alcohol alkoxylate adjuvants of the present invention.

[0036] The compositions of the present invention may include other adjuvants. Suitable adjuvants are known to those skilled in the art, examples of which are given in Hazen, Weed Technology, 2000, 14, 773-784, “Adjuvants – terminology, classification and chemistry”. Examples are surfactants (e.g., nonionic, anionic, cationic, or amphoteric), wetting agents, spreading agents, adhesives, humectants, and penetrants. Further examples of suitable adjuvants are mineral oils, vegetable oils, fatty acid esters, esters of aliphatic or aromatic dicarboxylic acids, alcohol ethoxylates, alkylphenol ethoxylates, alkylamine ethoxylates, triglyceride ethoxylates, fatty acid ethoxylates, fatty acid ester ethoxylates, sorbitol fatty acid ester ethoxylates, alkyl polyglycosides, and silicone-based adjuvants. Preferred suitable adjuvants are surfactants that provide improved wetting properties or improved spray retention properties.

[0037] The following examples demonstrate the effects of the adjuvants of the present invention on biological performance; the adjuvants used are listed together with the comparative adjuvants in Table A. Other comparative adjuvants used are the commercial adjuvants ATPLUS® 411 F (mineral oil adjuvant); Turbocharge® (oil-adjuvant blend); Tween® 20 (polyoxyethylene sorbitan laurate adjuvant); and adjuvant tris(2-ethylhexyl) phosphate [TEHP].

[0038] Table A

[0039]

[0040] In one aspect of the invention, adjuvant 1 is preferred; in an alternative aspect, adjuvant 2 is preferred; and in another alternative aspect, adjuvant 5 is preferred.

[0041] Example 1

[0042] The efficacy of adjuvant 1 as an adjuvant for the herbicide nicosulfuron was tested in a greenhouse against four weed species. Nicosulfuron was added to a spray can as a standard WG (water-dispersible granules) formulation.

[0043] Nicosulfuron was sprayed onto plants at a rate of 30 g and 60 g of pest control per hectare using a laboratory track sprayer (delivering the aqueous spray composition at a rate of 200 liters per hectare) without adjuvants. Spray tests were also conducted using nicosulfuron with adjuvants 1, 3, 4, or the commercially available canned adjuvant Atplus 411F®. Adjuvants were added to the spray solution at a rate of 0.2% v / v, and adjuvants other than Atplus 411F® were added at a rate of 0.5% v / v. The weed species and their growth stages at the time of spraying were Abutilon (growth stage 13), Cheal (growth stages 13-14), Digitaria (growth stages 13-21), and Setiu (growth stages 14-21).

[0044] Each spray test was repeated three times. Herbicide efficacy was visually assessed and expressed as the percentage of leaf area killed. Samples were evaluated at a 21-day post-application timeframe. The results shown in Table 1 below are the mean average for both ratios of nicosulfuron, three replicates, and four weed species.

[0045] Table 1

[0046] Average percentage kill results of nicosulfuron with different adjuvants

[0047]

[0048] The results showed that adjuvant 1 was an effective adjuvant for nicosulfuron and was at least as effective as the commercially available canned adjuvant Atplus411F®. Adjuvant 1 demonstrated better efficacy for nicosulfuron compared to the comparative alkoxylated adjuvants adjuvant 3 and adjuvant 4.

[0049] Example 2

[0050] The efficacy of adjuvant 1 as an adjuvant for the herbicide mesotrione was tested in a greenhouse against four weed species. Mesotrione was added to the spray can as a standard SC (suspension concentrate) formulation.

[0051] Using a laboratory track sprayer (delivering the aqueous spray composition at a rate of 200 liters / ha), nicosulfuron was sprayed onto plants at rates of 30 g and 60 g of pest control per hectare (without adjuvants). Spray tests were also conducted using nicosulfuron with adjuvants 1, 3, 4, or the well-known adjuvant Tween® 20. Adjuvants were added to the spray solution at a rate of 0.2% v / v, except for Tween® 20, which was added at a rate of 0.5% v / v. The four weed species tested were Polygonum cuspidatum (POLCO; growth stages 13–15), Plantago asiatica (BRAPL; growth stages 13–21), Commelina communis (COMBE; growth stages 12–13), and Digitaria sanguinalis (DIGSA; growth stages 13–14).

[0052] Each spray test was repeated three times. Herbicide efficacy was visually assessed and expressed as the percentage of leaf area killed. Samples were evaluated at a 21-day post-application timeframe. The results shown in Table 2 below are the average values ​​for both ratios of mesotrione, three replicates, and four weed species.

[0053] Table 2

[0054] Average percentage kill results of nicosulfuron with different adjuvants

[0055]

[0056] The results showed that adjuvant 1 was an effective adjuvant for mesotrione and was almost as effective as the known adjuvant Tween®20. Compared with the comparative alkoxylated adjuvants adjuvant 3 and adjuvant 4, adjuvant 1 showed better efficacy for mesotrione.

[0057] Example 3

[0058] The efficacy of adjuvant 1 as an adjuvant for the herbicide clodinafop-propargyl was tested in a greenhouse against four weed species. Clodinafop-propargyl was added to the spray can as a standard EC (emulsifiable concentrate) formulation.

[0059] Using a laboratory track sprayer (delivering the aqueous spray composition at a rate of 200 liters / ha), herbicides were sprayed onto plants at a rate of 7.5 g and 15 g of the herbicide per hectare (without adjuvants). Spray tests were also conducted using herbicides with adjuvants 1, 3, 4, or the standard adjuvant tri(2-ethylhexyl) phosphate. The adjuvants were added to the spray solution at a rate of 0.2% v / v. The weed species and their growth stages at the time of spraying were: Alomy (growth stage 12-13), Avefa (growth stage 12-13), Lolpe (growth stage 13), and Setvi (growth stage 12-13). Each spray test was repeated three times. The efficacy of the herbicide was visually assessed and expressed as the percentage of leaf area killed. Samples were evaluated at a time point of 21 days post-application. The results shown in Table 3 below are the average values ​​for two ratios of clopyralid, three replicates, and four weed species.

[0060] The results showed that adjuvant 1 was an effective adjuvant for clodinafop-propargyl and was almost as effective as the standard adjuvant tri(2-ethylhexyl) phosphate (which is a very effective adjuvant for clodinafop-propargyl). Compared with the comparative alkoxylated adjuvants adjuvant 3 and adjuvant 4, adjuvant 1 showed better efficacy for clodinafop-propargyl.

[0061] Table 3

[0062] Average percentage kill results of cyclohexane with different adjuvants

[0063]

[0064] Example 4

[0065] The efficacy of adjuvant 1 as an adjuvant for the herbicide flumetsulam (as sodium salt) was tested in a greenhouse against four weed species. Flumetsulam sodium salt was added to the spray can as a standard SL (soluble concentrate) formulation.

[0066] Using a laboratory track sprayer (delivering the aqueous spray composition at a rate of 200 liters / ha), flufenacet was sprayed onto plants at a rate of 60 g and 120 g of pest control per hectare (without adjuvants). Spray tests were also conducted using flufenacet with adjuvants 1, 3, 4, or the commercially available adjuvant Turbocharge®. Adjuvants were added to the spray solution at a rate of 0.2% v / v, while those other than Turbocharge® were added at a rate of 0.5% v / v. The weed species and their growth stages at the time of spraying were: cheal (growth stages 13–15), abutilon (growth stages 12–14), foxtail (setvi (growth stages 13–21), and dayflower (growth stages 12–13).

[0067] Each spray test was repeated three times. Herbicide efficacy was visually assessed and expressed as the percentage of leaf area killed. Samples were evaluated at a 21-day post-application timeframe. The results shown in Table 4 below are averages for both ratios of flufenacet, three replicates, and four weed species.

[0068] Table 4

[0069] Average percentage kill results of flusulfanil with different adjuvants

[0070]

[0071] Results demonstrated that adjuvant 1 was an effective adjuvant for flumetsulam, and at least as effective as the commercially available agrochemical adjuvant Turbocharge®. Adjuvant 1 showed better efficacy for flumetsulam compared to the comparative alkoxylated adjuvants 3 and 4.

[0072] Example 5

[0073] The efficacy of Adjuvant 2 as an adjuvant for the herbicide nicosulfuron was tested in a greenhouse against four weed species. Nicosulfuron was added to a spray can as a standard WG (water-dispersible granules) formulation.

[0074] Nicosulfuron was sprayed onto plants at rates of 30 g and 60 g of pest control per hectare (without adjuvants) using a laboratory track sprayer (delivering the aqueous spray composition at a rate of 200 liters per hectare). Spray tests were also conducted using nicosulfuron with adjuvant 2 or the commercially available canned adjuvant Atplus 411F®. These adjuvants were added to the spray solution at rates of 0.2% v / v or 0.5% v / v, respectively. The weed species were abutilon (Abutilon theophrasti), cheal (Chenopodium album), crabgrass (Digitaria sanguinalis), and foxtail (Setius spp.).

[0075] Each spray test was repeated three times. Herbicide efficacy was visually assessed and expressed as the percentage of leaf area killed. Samples were evaluated at a 21-day post-application timeframe. The results shown in Table 5 below are averages for both ratios of nicosulfuron, three replicates, and four weed species.

[0076] Table 5

[0077] Average percentage kill results of nicosulfuron with different adjuvants

[0078]

[0079] The results showed that adjuvant 2 was an effective adjuvant for nicosulfuron and was at least as effective as the commercially available canned adjuvant Atplus411F®.

[0080] Example 6

[0081] The efficacy of adjuvant 2 as an adjuvant for the herbicide mesotrione was tested in a greenhouse against four weed species. Mesotrione was added to the spray can as a standard SC (suspension concentrate) formulation.

[0082] Mesotrione was sprayed onto plants at rates of 30 g and 60 g per hectare of the herbicide (without adjuvants) using a laboratory track sprayer (delivering the aqueous spray composition at a rate of 200 liters per hectare). Spray tests were also conducted using mesotrione with adjuvant 2 or the well-known adjuvant Tween® 20. These adjuvants were added to the spray solution at rates of 0.2% v / v or 0.5% v / v, respectively. The four weed species were *Polygonum cuspidatum* (POLCO), *Plantago asiatica* (BRAPL), *Commelina communis* (COMBE), and *Digitaria sanguinalis* (DIGSA). Each spray test was repeated three times. The efficacy of the herbicide was visually assessed and expressed as the percentage of leaf area killed. Samples were evaluated at a 21-day post-application timeframe. The results shown in Table 6 below are the average values ​​for both rates of mesotrione, the three replicates, and the four weed species.

[0083] Table 6

[0084] Average percentage kill results of nicosulfuron with different adjuvants

[0085]

[0086] The results showed that adjuvant 2 was an effective adjuvant for mesotrione and was at least as effective as the well-known adjuvant Tween®20.

[0087] Example 7

[0088] The efficacy of adjuvant 2 as an adjuvant for the herbicide clodinafop-propargyl was tested in a greenhouse against four weed species. Clodinafop-propargyl was added to the spray can as a standard EC (emulsifiable concentrate) formulation.

[0089] Using a laboratory track sprayer (delivering the aqueous spray composition at a rate of 200 liters / ha), clodinafop-propargyl was sprayed onto plants at a rate of 7.5 g and 15 g of the pesticide per hectare (without adjuvant). Spray tests were also conducted using clodinafop-propargyl with adjuvant 2 or the standard adjuvant tris(2-ethylhexyl) phosphate. These adjuvants were added to the spray solution at a rate of 0.2% v / v. The weed species were Alomy, Avefa; perennial ryegrass (Lolpe), and Setvi (Setvi).

[0090] Each spray test was repeated three times. Herbicide efficacy was visually assessed and expressed as the percentage of leaf area killed. Samples were evaluated at a 21-day post-application timeframe. The results shown in Table 7 below are averages for two ratios of clodinafop-propargyl, three replicates, and four weed species.

[0091] The results showed that adjuvant 2 was an effective adjuvant for clodinafop-propargyl and was almost as effective as the standard adjuvant tri(2-ethylhexyl) phosphate (which is a very effective adjuvant for clodinafop-propargyl).

[0092] Table 7

[0093] Average percentage kill results of cyclohexane with different adjuvants

[0094]

[0095] Example 8

[0096] The efficacy of adjuvant 2 as an adjuvant for the herbicide flumetsulam (as sodium salt) was tested in a greenhouse against four weed species. Flumetsulam sodium salt was added to the spray can as a standard SL (soluble concentrate) formulation.

[0097] Using a laboratory track sprayer (delivering the aqueous spray composition at a rate of 200 liters / ha), flufenacet was sprayed onto plants at rates of 60 grams and 120 grams of pest control per hectare (without adjuvants). Spray tests were also conducted using flufenacet with adjuvant 2 or the commercially available agrochemical adjuvant Turbocharge®. These adjuvants were added to the spray solution at rates of 0.2% v / v or 0.5% v / v, respectively. The weed species were CHEAL, ABUTH, SETVI, and XANST.

[0098] Each spray test was repeated three times. Herbicide efficacy was visually assessed and expressed as the percentage of leaf area killed. Samples were evaluated at a 21-day post-application timeframe. The results shown in Table 8 below are averages for both ratios of flufenacet, three replicates, and four weed species.

[0099] Table 8

[0100] Average percentage kill results of flusulfanil with different adjuvants

[0101]

[0102] The results showed that adjuvant 2 was an effective adjuvant for flusulfanilamide and was almost as effective as the commercially available agrochemical adjuvant Turbocharge®.

[0103] Example 9

[0104] The efficacy of adjuvant 5 as an adjuvant for the herbicide nicosulfuron was tested in a greenhouse against four weed species. Nicosulfuron was added to the spray can as a standard SC (suspension concentrate) formulation.

[0105] Using a laboratory track sprayer (delivering the aqueous spray composition at a rate of 200 liters / ha), nicosulfuron was sprayed onto the plants at a rate of 30 or 60 grams of pest control per hectare (without adjuvants). Spray tests were also conducted using nicosulfuron with adjuvants 5, 6, or the well-known adjuvant Tween® 20. Adjuvants were added to the spray solution at a rate of 0.2% v / v, except for Tween® 20, which was added at a rate of 0.5% v / v. The four weed species tested were Polygonum cuspidatum (POLCO), Braplandia diffusa (BRAPL), Commelina communis (COMBE), and Digitaria sanguinalis (DIGSA).

[0106] Each spray test was repeated three times. Herbicide efficacy was visually assessed and expressed as the percentage of leaf area killed. Samples were evaluated at a 21-day post-application timeframe. The results shown in Table 9 below are the average values ​​for both ratios of nicosulfuron, three replicates, and four weed species.

[0107] Table 9

[0108] Average percentage kill results of nicosulfuron with different adjuvants

[0109]

[0110] The results showed that adjuvant 5 was an effective adjuvant for mesotrione and was more effective than the known adjuvant Tween®20. Adjuvant 5 also showed better efficacy for mesotrione compared to the control adjuvant 6.

[0111] Example 10

[0112] The efficacy of adjuvant 5 as an adjuvant for the herbicide clodinafop-propargyl was tested in a greenhouse against four weed species. Clodinafop-propargyl was added to the spray can as a standard EC (emulsifiable concentrate) formulation.

[0113] Using a laboratory track sprayer (delivering the aqueous spray composition at a rate of 200 liters / ha), clodinafop-propargyl was sprayed onto plants at a rate of 7.5 g or 15 g of the herbicide per hectare (without adjuvants). Spray tests were also conducted using clodinafop-propargyl with adjuvants 5, 6, or the standard adjuvant tri(2-ethylhexyl) phosphate. The adjuvants were added to the spray solution at a rate of 0.2% v / v. The weed species were Alomy, Avefa, Lolpe, and Setvi. Each spray test was repeated three times. The efficacy of the herbicide was visually assessed and expressed as the percentage of leaf area killed. Samples were evaluated at a 21-day post-application timeframe. The results shown in Table 10 below are the average values ​​for clodinafop-propargyl at both rates, in three replicates, and on the four weed species.

[0114] The results showed that adjuvant 5 was an effective adjuvant for clodinafop-propargyl and was almost as effective as the standard adjuvant tri(2-ethylhexyl) phosphate (which is a very effective adjuvant for clodinafop-propargyl). Compared with the control adjuvant 6, adjuvant 5 showed better efficacy for clodinafop-propargyl.

[0115] Table 10

[0116] Average percentage kill results of cyclohexane with different adjuvants

[0117]

[0118] Example 11

[0119] Adjuvant 1 was tested as an adjuvant for use in agricultural chemical compositions containing pyraclostrobin.

[0120] Two-week-old wheat plants were inoculated with the fungus *Syngonium vesicanthum*. Four days post-inoculation, the plants were sprayed with a diluted suspension concentrate of the fungicide pyraclostrobin (without adjuvant) at 2 bar using a laboratory tracked sprayer (delivering an aqueous spray composition at a rate of 200 liters / ha) and a flat fan nozzle (LU 90-01). The concentration of the fungicide was 6.5, 16, 40, or 100 mg per liter of spray solution. Spray tests were also performed using a diluted suspension concentrate of pyraclostrobin, additionally containing adjuvant 1, which was added to the spray solution at a rate of 0.1% v / v based on the volume of spray solution. Fourteen days post-infection, the leaves of the plants were visually assessed, and damage was expressed as a percentage of infected leaf area. Each spray test was repeated four times at the four application rates.

[0121] The results shown in Table 11 below are the average values ​​of pyraclostrobin at four ratios and four replicates.

[0122] Table 11

[0123] Average % infection rate of wheat plants under *Nepeta spp.* serotype after treatment with pyraclostrobin.

[0124]

[0125] As can be seen from Table 11, compared with the results obtained by pyraclostrobin SC without adjuvant, the inclusion of adjuvant 1 as an adjuvant of pyraclostrobin resulted in a significant reduction in the percentage of wheat husk spore infection.

Claims

1. Use of compounds having formula (I) for improving the biological properties of agrochemicals. RO-[PO] m -[IS] n -HER) in, R is C 16 To C 18 Straight-chain or branched alkyl or alkenyl, PO represents propylene oxide unit, EO represents ethylene oxide unit, m is from 4 to 9 and n is from 4 to 15.

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