5-phenyl substituted isoxazole compounds as growth regulators and methods of use thereof

Abstract

The application provides application of a compound of formula (I) as a plant growth regulator, wherein definitions of X, R1, R2 and n are as defined in the description. The compound of formula (I) has good plant growth regulation effect and has wide application prospect.

Description

Technical Field

[0001] This invention relates to the field of pesticides, specifically to 5-phenyl-substituted isoxazole compounds as growth regulators and methods of application thereof. Background Technology

[0002] With the development of science and technology and agricultural modernization, plant growth regulators are widely used in crop production, especially in controlling plant growth and development, where they play a crucial role. Both domestically and internationally, the use of plant growth regulators to control plant growth and development has been recognized as one of the main measures for achieving crop stress resistance and yield increase in the 21st century.

[0003] Numerous studies have shown that plant growth regulators can regulate the synthesis of nucleic acids, proteins, and enzymes within plants, playing a regulatory and controlling role in different stages of plant growth and development, such as germination, rooting, cell elongation, organ differentiation, flower bud differentiation, flowering, fruiting, leaf fall, and dormancy. In recent years, the research and development of plant growth regulators has progressed rapidly, and they have been widely applied in agricultural, forestry, and horticultural crop production. They have played a significant role, particularly in regulating plant growth and nutrient formation and distribution, promoting individual growth and development, enhancing crop resistance, increasing crop yield, improving product quality, and enhancing planting efficiency. Furthermore, the use of plant growth regulators can also improve fertilizer utilization efficiency and labor productivity, making it a technology with broad application prospects.

[0004] Isoxazole compounds, as a class of heterocyclic compounds with good biological activity and potential medicinal value, have long attracted attention and research. Some 5-phenyl-substituted isoxazole compounds are commonly used as herbicide safeners. For example, patent CN1133038A discloses that ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate can be used as a herbicide safener; patent CN102227162A discloses a combination of ethyl 5-phenyl-2-isoxazolin-3-carboxylate and a herbicide, which can reduce the damage of herbicides to crops. No existing technical literature records or suggests that 5-phenyl-substituted isoxazole compounds possess plant growth regulating activity. Summary of the Invention

[0005] Extensive research in our laboratory has revealed that the 5-phenyl-substituted isoxazole compounds represented by formula (I) possess excellent plant growth regulatory activities.

[0006] Specifically, this invention provides the application of compounds with the structure shown in formula (I) as plant growth regulators.

[0007]

[0008] Wherein, X can be the same or different, and is selected from one of the following: optionally substituted alkyl, optionally substituted alkoxy, cyano, ester, nitro, amino, amide, halogen and haloalkyl;

[0009] R1 is selected from one of hydrogen, optionally substituted alkyl, optionally substituted alkoxy-alkyl, optionally substituted cycloalkyl, optionally substituted heterocyclic and optionally substituted aryl;

[0010] R2 is selected from hydrogen or optionally substituted alkyl groups;

[0011] n is a natural number selected from 0 to 5, with 0, 1, 2 and 3 being particularly preferred.

[0012] The present invention provides a method for treating seeds or plants by applying a compound containing the compound shown in formula (I) of the present invention to the seeds or plants.

[0013] The present invention also provides a medicated fertilizer that promotes plant health, comprising the compound represented by formula (I) of the present invention and conventional fertilizer.

[0014] A medicated fertilizer for regulating plant growth contains the compound represented by formula (I) of this invention and conventional fertilizers.

[0015] Beneficial effects of the invention

[0016] The plant growth regulator of this invention can promote plant growth and development, increase crop and vegetable yields, and exhibit excellent plant growth regulation effects. Detailed Implementation

[0017] The endpoints and any values ​​of the ranges disclosed herein are not limited to the precise ranges or values, and these ranges or values ​​should be understood to include values ​​close to these ranges or values. For numerical ranges, the endpoint values ​​of the various ranges, the endpoint values ​​of the various ranges and individual point values, and individual point values ​​can be combined with each other to obtain one or more new numerical ranges, which should be considered as specifically disclosed herein.

[0018] The following provides a detailed description of specific embodiments of the present invention. It should be understood that the specific embodiments described herein are for illustrative and explanatory purposes only and are not intended to limit the scope of the invention.

[0019] The term "plant growth regulator" refers to substances that can delay or accelerate seed germination, delay or accelerate plant growth, or promote healthy plant growth and increase plant yield. Specific functions include: preventing or delaying seed germination, promoting or stimulating seed reproduction, and regulating plant growth.

[0020] The term "halogen" in this invention refers to fluorine, chlorine, bromine, and iodine.

[0021] The term "alkyl" (and in other groups containing alkyl, such as the alkyl portion of an alkoxy group, the alkyl portion of an arylalkyl group) in each case generally means a straight-chain or branched alkyl group having 1-20 carbon atoms, often 1-6 carbon atoms, preferably 1-4 carbon atoms, and especially 1-3 carbon atoms. Examples of C1-C4 alkyl groups are methyl, ethyl, n-propyl, isopropyl, n-butyl, 1-methylpropyl (sec-butyl), 2-methylpropyl (isobutyl), and 1,1-dimethylethyl (tert-butyl). Examples of C1-C6 alkyl groups, in addition to those mentioned for C1-C4 alkyl groups, include n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, or 1-ethyl-2-methylpropyl. Examples of C1-C10 alkyl groups, in addition to those mentioned for C1-C6 alkyl groups, include n-heptyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 1-ethylhexyl, 2-ethylhexyl, 1,2-dimethylhexyl, 1-propylpentyl, 2-propylpentyl, nonyl, decyl, 2-propylheptyl, and 3-propylheptyl, but are not limited thereto. The term "alkoxy" in this invention refers to an -OR group, where R is an alkyl group as defined above, typically having 1-6 carbon atoms, preferably 1-4 carbon atoms, and especially a straight-chain or branched alkyl group with 1-3 carbon atoms. Examples include methoxy, ethoxy, propoxy, or 2-propoxy, n-butoxy, isobutoxy, or tert-butoxy, but are not limited thereto.

[0022] In this invention, the term "amide group" refers to a group containing "-NHCO-" or "-CONHCO-". Examples of such amide groups include, but are not limited to, -NHCOCH3, -NHCOH, -NHCOCH2CH3, -NHCOCH2CH2CH3, -NHCOCH(CH3)2, -N(COCH3)2, -CONH2, -CON(CH3)2, -CONHCH3, -CONHCH2CH3, -CON(CH2CH3)2, -CONHCH(CH3)2, -CONHCH2CH2CH3, -CONHCH2CH2CH2CH3, phthalimide, succinimide, glutarimide, maleimide, etc.

[0023] The term "ester group" in this invention refers to a group containing "-COO-", such as -COOCH3, -COOCH2CH3, -COOCH(CH3)2, -COOCH2CH2CH3, -COOCH2CH2CH2CH3, but not limited thereto.

[0024] The term "halogenated alkyl" in this invention refers to a partially or fully halogenated alkyl group, wherein the alkyl group has the meaning of the above-described alkyl group, wherein the halogen atom is in particular fluorine, chlorine and / or bromine, i.e., for example, chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2-chloro-2-fluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-1,1,2-trifluoroethyl, 2-chloro-2,2 -Difluoroethyl, 2-bromo-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, 1,1,2,2-tetrafluoroethyl, 1,1,2,2-tetrachloroethyl, pentafluoroethyl, 2,2,3,3-tetrafluoro-1-propyl, 1,1,2,3,3,3-hexafluoro-1-propyl, 1,1,1,3,3,3-hexafluoro-2-propyl, heptafluoro-1-propyl, heptafluoro-2-propyl, 2,2,3,3,4,4,4-heptafluoro-1-butyl or nonafluoro-1-butyl, etc., but not limited to these.

[0025] In this invention, the term "cycloalkyl" refers to a monocyclic monovalent hydrocarbon group of three to eight carbon atoms, which may be saturated or contain a double bond. Cycloalkyl groups may be unsubstituted or substituted with one or two substituents independently selected from alkyl, halogen, alkoxy, hydroxy, or cyano groups, but are not limited thereto. Examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-cyanocyclopropyl-1-yl, 1-cyanomethylcyclopropyl-1-yl, 3-fluorocyclohexyl, etc. When a cycloalkyl group contains a double bond, it may be referred to herein as a cycloalkenyl group.

[0026] The term "heterocycle" in this invention refers to a saturated or partially unsaturated carbon ring containing one to four heteroatoms selected from nitrogen, oxygen, and sulfur as ring members. Such a ring does not contain adjacent oxygen atoms, adjacent sulfur atoms, or adjacent oxygen and sulfur atoms within the ring. Preferred examples are aziridine, aziridine butane, pyrrolidine, piperidine, morpholine, piperazine, homopiperazine, tetrahydrofuran, dioxane, 2,5-diazabicyclo[2,2,1]heptane, and 3,7-diazabicyclo[3,3,0]octane, and more preferably aziridine, aziridine butane, pyrrolidine, piperidine, morpholine, piperazine, homopiperazine, 2,5-diazabicyclo[2,2,1]heptane, and 3,7-diazabicyclo[3,3,0]octane.

[0027] In this invention, "aryl" refers to a monovalent monocyclic or bicyclic aromatic hydrocarbon group with 6 to 10 ring atoms, such as phenyl or naphthyl, especially phenyl, but not limited thereto.

[0028] The term "heteroaryl" in this invention refers to an aromatic ring system containing at least one heteroatom selected from nitrogen, oxygen, and sulfur, and preferably at most three heteroatoms as ring members. The heteroaryl ring does not contain adjacent oxygen atoms, adjacent sulfur atoms, or adjacent oxygen and sulfur atoms within the ring. Preferred examples include, but are not limited to, pyrrolidine, piperidine, piperazine, morpholine, pyridine, pyrimidine, pyrazine, pyridazine, pyrrole, pyrazole, imidazole, triazole, isoxazole, oxazole, isothiazole, thiazole, tetrazolium, furan, and thiophene, etc.

[0029] The term "optional substitution" means that the relevant group may or may not be substituted by a substituent. When a group is described as optionally substituted, it is preferable to have 1-5 optional substituents, more preferably 1-3 optional substituents, and even more preferably 1 or 2 optional substituents. When a group is described as optionally substituted, and the optional substitution of the group involves more than one substituent, the more than one substituent can be the same or different. The substituent can be alkyl, halogen, cyano, nitro, aryl, cycloalkyl, heterocyclic, amide, ester, etc., but is not limited thereto.

[0030] The term "pesticide-acceptable salt" refers to a pharmaceutically acceptable organic or inorganic salt of the compounds of the present invention. Exemplary acid addition salts include, but are not limited to, salts of inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid, and phosphoric acid, or salts of organic acids such as methanesulfonic acid, p-toluenesulfonic acid, lactic acid, malic acid, tartaric acid, acetic acid, trifluoroacetic acid, citric acid, succinic acid, fumaric acid, maleic acid, and salicylic acid; exemplary base addition salts include, but are not limited to, salts of inorganic bases such as lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, magnesium hydroxide, and ammonium hydroxide monohydrate, or salts of organic bases such as pyridine, piperidine, and triethylamine.

[0031] The term "conventional fertilizers" in this invention refers to: nitrogen fertilizers including ammonium bicarbonate, ammonium chloride, ammonium sulfate, ammonia water, urea, ammonium nitrate, sodium nitrate, calcium nitrate, calcium cyanamide, etc.; phosphate fertilizers including phosphoric acid, superphosphate, triple superphosphate, calcium magnesium phosphate, dicalcium phosphate, calcium magnesium phosphate potassium fertilizer, defluorinated phosphate fertilizer, calcium metaphosphate, phosphate rock powder, bone meal, bird droppings phosphate fertilizer, phosphate fertilizer, calcium sodium phosphate, etc.; potassium fertilizers including potassium chloride, potassium sulfate, potassium carbonate, potassium magnesium fertilizer, potassium magnesium sulfate fertilizer, potassium calcium fertilizer, kiln ash potassium fertilizer, etc.; calcium fertilizers including lime, etc.; magnesium fertilizers including magnesium sulfate, magnesium nitrate, etc.; sulfur fertilizers including gypsum, sulfur, etc.; zinc fertilizers including zinc sulfate, zinc oxide, zinc chloride, etc.; and boron fertilizers including borax, boric acid, boron mud, and sulforaphane. Boron fertilizers include: polyboron, boron-containing fertilizers, active boron, and boron-enriched fertilizers; molybdenum fertilizers include ammonium molybdate, sodium molybdate, and molybdenum trioxide; manganese fertilizers include manganese sulfate; iron fertilizers include ferrous sulfate; copper fertilizers include copper sulfate; chlorine fertilizers; silicon fertilizers; rare earth fertilizers; microbial fertilizers including agricultural microbial agents, rhizobium fertilizers, nitrogen-fixing bacteria fertilizers, antibiotic fertilizers, phosphorus bacteria fertilizers, silicate bacteria fertilizers, photosynthetic bacteria agents, and bio-organic fertilizers; organic fertilizers including human excrement, manure, livestock excrement, poultry manure, compost, biogas fermentation tank fertilizer, compost, straw fertilizer, oilseed cake fertilizer, green manure, wood ash, miscellaneous soil fertilizer, and peat; foliar fertilizers and water-soluble fertilizers; pesticide fertilizers including herbicide fertilizers, insecticide fertilizers, and fungicide fertilizers; and compound fertilizers.

[0032] This invention provides the use of compounds of formula (I) or pesticide-acceptable salts thereof as plant growth regulators.

[0033]

[0034] Wherein, X can be the same or different, and is selected from one of the following: optionally substituted alkyl, optionally substituted alkoxy, cyano, ester, nitro, amino, amide, halogen and haloalkyl;

[0035] R1 is selected from one of hydrogen, optionally substituted alkyl, optionally substituted alkoxy-alkyl, optionally substituted cycloalkyl, optionally substituted heterocyclic, optionally substituted aryl, and optionally substituted heteroaryl.

[0036] R2 is selected from hydrogen or optionally substituted alkyl groups;

[0037] n is a natural number selected from 0 to 5, with 0, 1, 2 and 3 being particularly preferred.

[0038] Preferably, X is selected from one of the following: optionally substituted C1-C6 alkyl groups, optionally substituted C1-C6 alkoxy groups, cyano groups, ester groups, nitro groups, amino groups, amide groups, halogens, and halogenated C1-C6 alkyl groups; particularly preferred are -CH3, -C2H5, -C3H7, -C4H9, and -C5H. 11 -C6H 13, -OCH3, -OC2H5, -OC3H7, -OC4H9, -OC5H 11 -OC6H 13 , -COO(CH3), -COO(C2H5), -COO(C3H7), -COO(C4H9), -COO(C5H 11 -COO(C6H) 13 One of the following is present: -NO2, -CN, -NH2, -NHCH3, -NHCH2CH3, -N(CH3)2, -CO(NH2), -CO NHCH3, -CO NHCH2CH3, -CO N(CH3)2, -F, -Cl, -Br, -I, -CF3, -CHF2, and CH2F;

[0039] Preferably, R1 is selected from hydrogen, optionally substituted C1-C6 alkyl groups, optionally substituted C1-C6 alkoxy-C1-C6 alkyl groups, optionally substituted C3-C8 cycloalkyl groups, optionally substituted heterocyclic groups, and... One of them, particularly preferred are -CH3, -C2H5, -C3H7, -C4H9, and -C5H. 11 -C6H 13 , -CH2OCH3, -CH2OC2H5, -CH2OC3H7, -CH2OC4H9, -CH2CH2OCH3, -CH2CH2OC2H5, -CH2CH2O C3H7, -CH2 CH2OC4H9, -C3H6OCH3, -C3H6O C2H5, -C3H6O C3H7, -C4H8OCH3, -C4H8OC2H5, -C5H 10 O CH3、 One of them, wherein n is selected from natural numbers from 0 to 5, with 0, 1, 2 and 3 being particularly preferred.

[0040] R2 is selected from hydrogen or C1-C6 alkyl groups, preferably hydrogen, methyl, ethyl, propyl or isopropyl.

[0041] The compound particularly preferred by this invention is:

[0042] The present invention also provides a composition of a growth regulator comprising a compound of formula (I) of the present invention and a pesticide adjuvant.

[0043] Preferably, the content of the compound of formula (I) of the present invention in the above-mentioned growth regulator composition is 1-99%.

[0044] Preferably, the pesticide adjuvants in the above-mentioned growth regulator composition include one or more of the following: solvent, cosolvent, emulsifier, wetting agent, penetrant, dispersant, stabilizer, antifreeze, preservative, defoamer, thickener, disintegrant, binder, filler / carrier, etc.

[0045] The solvent and co-solvent are selected from one or more of the following: vegetable oil or methylated vegetable oil (including sunflower oil, cottonseed oil, palm oil, peanut oil, castor oil, soybean oil, rapeseed oil, corn oil, etc.), naphtha, liquid paraffin oil, benzene, toluene, xylene, naphthalene, acetonitrile, acetone, dimethyl sulfoxide, methanol, ethanol, ethylene glycol, isopropanol, cyclohexanol, dichloromethane, chloroform, cyclohexanone, N-methylpyrrolidone, acetate, etc.

[0046] The emulsifier is selected from one or more of the following: fatty alcohol polyoxyethylene ether, nonylphenol polyoxyethylene ether, fatty amine polyoxyethylene ether, alkyl glycoside, castor oil polyoxyethylene ether, polyoxyethylene oleate, ethylene oxide / propylene oxide co-ether, polyglycerol fatty acid ester, calcium dodecylbenzene sulfonate, polyoxyethylene ether sulfate salt, polyoxyethylene ether phosphate salt, agricultural emulsion 601#, agricultural emulsion 602#, agricultural emulsion 603#, agricultural emulsion 604#, agricultural emulsion 401#, agricultural emulsion 402#, agricultural emulsion 33#, agricultural emulsion 34#, agricultural emulsion 1601#, agricultural emulsion 1602#, agricultural emulsion 700#, Span-20, Span-40, Span-60, Span-65, Span-80, Span-85, Tween-20, Tween-40, Tween-60, Tween-65, Tween-80, and Tween-85.

[0047] The wetting agent and penetrant are selected from one or more of the following: castor oil polyoxyethylene ether, calcium dodecylbenzene sulfonate, sodium α-alkenyl sulfonate, isomeric alcohol ether 1300 series, MOA series, penetrant JFC, emulsifier AEO, agricultural emulsion 600#, agricultural emulsion 400#, agricultural emulsion 33#, agricultural emulsion 34#, TX series, OP series, NP series, AC-1800 series, AC-1200 series, AN-1800 series, C8-C10 alkyl glycoside, C12-C14 alkyl glycoside, C8-C14 alkyl glycoside, fast T, dispersant NNO, and pull-apart powder BX.

[0048] The dispersant is selected from naphthalene or alkylnaphthalene formaldehyde condensate sulfonate, lignin sulfonate, phosphate salt, polyoxyethylene ether sulfate salt, sodium succinate diester sulfonate salt, polycarboxylate salt, fatty alcohol polyoxypropylene polyoxyethylene ether, polyoxyethylene polyether block copolymer, etc.

[0049] The stabilizer is selected from one or more of the following: phosphite, epichlorohydrin, epoxidized soybean oil, epoxidized linseed oil, BHA, BHT, etc.

[0050] The antifreeze is selected from one or more of urea, ethylene glycol, propylene glycol, glycerol, and polyethylene glycol.

[0051] The preservative is selected from one or more of sorbic acid, hydroquinone, benzoic acid, and p-hydroxybenzoic acid.

[0052] The defoamer is selected from one or more of the following: polyether surfactants, mineral oil, tributyl phosphate, propanol, butanol, polyethylene glycol fatty acid esters, and siloxane oils.

[0053] The thickener is selected from one or more of the following: starch, magnesium aluminum silicate, xanthan gum, agar, hydroxymethyl cellulose, hydroxypropyl methyl cellulose, organobentonite, diatomaceous earth, polyvinyl alcohol, etc.

[0054] The disintegrant is selected from one or more of sodium carboxymethyl starch, croscarmellose sodium, croscarmellose cellulose, modified starch, croscarmellose polyvinylpyrrolidone, magnesium aluminum silicate, sodium alginate, etc.

[0055] The binder is selected from one or more of starch, gelatin and gum arabic, povidone, sucrose, glucose, and dextrin.

[0056] The carrier and filler are selected from one or more of the following: bentonite, diatomaceous earth, silica, starch, magnesium stearate, attapulgite, zeolite, sepiolite, clay, kaolin, talc, and light calcium carbonate.

[0057] The above-described growth regulator compositions of the present invention can be prepared into conventional formulations in the field, such as aqueous solutions, suspensions, water-dispersible granules, powders, wettable powders, dispersible oil suspensions, soluble powders / granules, emulsifiable concentrates, granules, water emulsions, etc., but are not limited thereto.

[0058] This invention provides a method for treating seeds or plants by applying a compound containing the compound shown in formula (I) of this invention to the seeds or plants. Preferred methods include seed dressing or foliar spraying.

[0059] The compound of formula (I) of this invention can be used in combination with herbicides, fungicides, insecticides, plant growth regulators, etc., as needed.

[0060] The present invention also provides a medicated fertilizer that promotes plant health, comprising the compound represented by formula (I) of the present invention and conventional fertilizer.

[0061] The present invention also provides a medicated fertilizer for regulating plant growth, comprising the compound represented by formula (I) of the present invention and conventional fertilizer.

[0062] The present invention will be further described below with reference to the embodiments. Unless otherwise specified, the raw materials, reagents, etc. used to prepare the compounds of the present invention are commercially available or can be prepared by conventional methods in the art.

[0063] I. Preparation Examples

[0064] Example 1: Synthesis of Compound 1

[0065]

[0066] Referring to patent 202311335008.9, 100 ml of dichloroethane was taken, and 7.58 g of 2-chloro-2-(hydroxyimino)ethyl acetate, 5.22 g of styrene and 5.15 g of triethylamine were added. The mixture was reacted at 80 °C for 2 h. After the reaction was completed, water was added for extraction, and the organic layer was concentrated to remove the solvent, yielding 10.85 g of compound 1, with a yield of 98.9%.

[0067] 1H NMR (300MHz, CDCl3) δ7.28-7.45(m,5H), δ5.77-5.83(t,1H), δ4.34-4.41(q,2H),

[0068] δ3.60-3.71(q,1H), δ3.19-3.28(q,1H), δ1.37-1.42(t,3H)

[0069] Implementation of Section 2 Synthesis of Compound 7

[0070]

[0071] Referring to patent 202311335008.9, 200 ml of benzene was taken, and 12.68 g of ethyl 5-chloro-5-phenyl-4,5-dihydroisoxazole-3-carboxylate and 7.3 g of aluminum trichloride were added. The mixture was reacted at 70 °C for 1 h. After the reaction was completed, hydrochloric acid was added to quench the reaction. The organic layer was taken and concentrated to remove the solvent, yielding compound 7 at 14.46 g, with a yield of 97.9%.

[0072] 1H NMR (300MHz, DMSO) δ7.25-7.44 (m, 10H), δ4.19-4.26 (q, 2H), δ3.91 (s, 2H), δ1.21-1.26 (t, 3H).

[0073] The following compounds of the present invention were prepared according to Examples 1 and 2 (see Table 1).

[0074] Table 1 Compounds of the present invention

[0075]

[0076]

[0077] II. Formulation Examples

[0078] Example 1: 10% Compound 2 aqueous solution

[0079] Compound 210%

[0080] Calcium dodecylbenzenesulfonate (70% isobutanol solution) 6%, polyethylene glycol 2%

[0081] 1% p-hydroxybenzoic acid

[0082] Water replenished to 100%

[0083] Example 2: 15% Compound 3 Suspension Agent Compound 3 15%

[0084] Agricultural Milk 1602# 4%

[0085] Fast T 2%

[0086] 1% hydroxymethylcellulose

[0087] 1% epoxidized linseed oil

[0088] Propanol 0.8%

[0089] Water replenished to 100%

[0090] Implementation List 3: 30% Compound 1 water-dispersible granules Compound 1 30%

[0091] Agricultural Milk 603# 4%

[0092] Calcium dodecylbenzenesulfonate 2%

[0093] Sodium carboxymethyl starch 1.2%

[0094] 1% urea

[0095] Starch replenishment to 100%

[0096] Example 4: 20% Compound 7 Dispersible Oil Suspension

[0097] Compound 7 20%

[0098] Calcium dodecylbenzenesulfonate (70% isobutanol solution) 2%

[0099] Castor oil polyoxyethylene ether 2%

[0100] xanthan gum 3%

[0101] Methyl oleate replenishment to 100%

[0102] Example 5: 70% Compound 10 emulsifiable concentrate

[0103] Compound 1070%

[0104] Tween-205%

[0105] 1% castor oil polyoxyethylene ether

[0106] 4% acetone

[0107] Naphtha replenishment 100%

[0108] Example 6: 5% Compound 5 wettable powder

[0109] 55% of the compound

[0110] 5% calcium dodecylbenzenesulfonate

[0111] 1% of the powder can be pulled apart

[0112] 100% replenishment of silica.

[0113] III. Plant Life Tests

[0114] 1. Rooting promotion experiment

[0115] Preparation of reagents: Weigh a certain amount of compounds 1-11, dissolve them in acetone, and dilute with 0.1% Tween 80 aqueous solution for later use.

[0116] Soil preparation and sowing: Use soil with 3% organic matter content, pH 7, and good permeability. Sift and air-dry the soil, then fill pots to 4 / 5 full. Thoroughly moisten the soil by bottom watering. Sow wheat seeds evenly on the soil surface, cover with 1cm of soil, and then transfer to a greenhouse for cultivation at approximately 20℃. Supplement watering by bottom watering. After emergence, select seedlings with uniform growth for thinning and transplanting.

[0117] Application of pesticide: Wheat was treated by root irrigation, with 4 replicates for each treatment. A control group without pesticide was included. Root length was recorded after 7 days, and the rooting promotion rate was calculated.

[0118] Formula for calculating rooting promotion rate:

[0119] R = Rooting Promotion Rate

[0120] X1 = Length of the taproot or lateral roots of the plant treated with the pesticide

[0121] X0 = Length of the taproot or lateral roots of the blank control plant

[0122] Table 2. The promoting effect of isoxazole compounds on wheat rooting

[0123]

[0124] As shown in Table 2, the compounds of this invention have a good promoting effect on wheat rooting. Among them, compounds 1 and 7 showed excellent effects even at low concentrations.

[0125] 2. Germination promotion experiment

[0126] The experimental methods were based on the standards NY / T 2061.1-2011 Guidelines for Indoor Bioassay of Pesticides - Plant Growth Regulators - Part 1 Tests for Promoting / Inhibiting Seed Germination - Soaking Method and GB / T3543.4-1995 Procedures for the Inspection of Crop Seeds - Germination Test.

[0127] Seed pretreatment: Take corn seeds that have passed dormancy and perform initial selection with distilled water, then sterilize with saturated sodium hypochlorite solution for 0.5 hours, rinse thoroughly with running water and set aside.

[0128] Preparation of reagents: Weigh a certain amount of compounds 1-11, dissolve them in acetone, and dilute with 0.1% Tween 80 aqueous solution for later use.

[0129] Seed soaking: After detoxification, the seeds were soaked in the solution for 12 hours. A blank control treatment without the solution was also provided. After soaking, the seeds were rinsed 5 times with distilled water and dried with filter paper before use.

[0130] Germination experiment: Place three layers of qualitative filter paper on a germination dish, moisten the filter paper with distilled water, drain off excess water, place 25 corn seeds on the dish, and cover with another layer of moistened filter paper. Repeat each treatment four times. Transfer the dish to an artificial climate chamber and incubate at 25°C, keeping the filter paper moist. Observe and record the germination status of the corn after 7 days.

[0131] Table 3. The promoting effect of isoxazole compounds on maize seed germination.

[0132]

[0133] As shown in Table 3, the compounds of the present invention have a good promoting effect on the germination of maize seeds.

[0134] 3. Promotes growth

[0135] The experimental method references the standard NY / T 2061.2-2011 Guidelines for Indoor Bioassay of Pesticides - Plant Growth Regulators - Part 2: Tests for Promoting / Inhibiting Plant Growth - Foliar Spray Method.

[0136] Preparation of reagents: Weigh a certain amount of compounds 1-11, dissolve them in acetone, and dilute with 0.1% Tween 80 aqueous solution for later use.

[0137] Soil preparation and sowing: Use soil with 3% organic matter content, pH 7, and good permeability. Sift and air-dry the soil, then fill pots to 4 / 5 full. Use bottom irrigation to thoroughly moisten the soil. Sow rice seeds evenly on the soil surface, cover with 1cm of soil, and then move to a greenhouse for cultivation at approximately 20℃. Water as needed (irrigate the pots from the top until saturated). Thin and transplant seedlings as appropriate after emergence.

[0138] Application: Spray the pesticide at the 3-4 leaf stage of the crop. Each treatment was replicated 4 times, and a control group without pesticide was included. After treatment, allow the pesticide solution to air dry naturally, then transfer the crop to a greenhouse for conventional cultivation. Replenish water as needed. Record the fresh weight of each treatment after 15 days and calculate the fresh weight promotion rate.

[0139] Formula for calculating fresh weight promotion rate:

[0140] R = Fresh weight promotion rate

[0141] X1 = Fresh weight of the plant treated with the pesticide

[0142] X0 = Fresh weight of blank control plants

[0143] Table 4. The promoting effect of isoxazole compounds on rice growth

[0144]

[0145]

[0146] As shown in Table 4, the compounds of this invention have a significant effect on promoting the growth of rice.

[0147] 4. Yield Increase Experiment

[0148] Preparation of reagents: Weigh a certain amount of compounds 1-11, dissolve them in acetone, and dilute them with a 0.1% Tween 80 aqueous solution for later use.

[0149] Experimental fields: Experimental fields for corn and wheat were selected in Zhengzhou, Henan Province, and experimental fields for rice were selected in Xinyang, Henan Province. The corn variety was Zhengdan 958, the rice variety was Zhengdao 19, and the wheat variety was Zhengmai 379.

[0150] Application of pesticides: When crops are at the 3-4 leaf stage, pesticides are sprayed at random sites with a treatment area of ​​50 square meters. A treatment without pesticides is set up as a blank control. Each treatment has 4 replicates. Field management is carried out for each treatment in the same way and at the same time. After harvest, the average yield of each treatment is recorded and calculated.

[0151] Table 5. Effects of isoxazole compounds on maize yield.

[0152]

[0153]

[0154] Table 6. Effects of isoxazole compounds on rice yield.

[0155]

[0156]

[0157] Table 7. Effects of isoxazole compounds on wheat yield.

[0158]

[0159] As can be seen from the data in Tables 5-7, the compounds of the present invention have a significant effect on increasing plant yield.

[0160] Although the present invention has been described in detail above with general descriptions and specific embodiments, modifications or improvements can be made to it, which will be obvious to those skilled in the art. Therefore, all such modifications or improvements made without departing from the spirit of the present invention fall within the scope of protection claimed by the present invention.

Claims

1. The application of compounds of formula (I) or their pesticide-acceptable salts as plant growth regulators, （I）。 2. A composition of a growth regulator comprising the compound of formula (I) as claimed in claim 1 or a pesticide-acceptable salt thereof and a pesticide adjuvant, wherein the content of the compound of formula (I) or a pesticide-acceptable salt thereof in the composition is 1-99%.

3. A medicated fertilizer for regulating plant growth, characterized in that, Contains a compound of formula (I) as claimed in claim 1 or a pesticide-acceptable salt thereof, or a composition as claimed in claim 2, as well as conventional fertilizers.

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