CN114158553A - Novel pesticide preparation and preparation method thereof - Google Patents

Abstract

The invention provides a novel pesticide preparation and a preparation method thereof, and the components of the pesticide preparation comprise a pesticide active ingredient and calixarene, wherein the pesticide active ingredient has an aromatic ring and forms bonding with the calixarene, so that the pesticide preparation has the advantage of being capable of solubilizing. The dosage of organic reagent in the pesticide preparation is greatly reduced, and the toxicity in organisms and soil can be reduced.

Description

Novel pesticide preparation and preparation method thereof

Technical Field

The invention belongs to the technical field of pesticides, and particularly relates to a pesticide preparation (pesticide composition) and a preparation method thereof.

Background

Because the original pesticide has the problems of poor water solubility, unstable environment, low bioavailability and the like, the original pesticide needs to be added with an auxiliary agent to form a pesticide preparation for use in practical application. The traditional formulation still accounts for the main part of the existing pesticide auxiliary agents in China. The novel pesticide formulation is continuously developed in recent years, and particularly, the proportion of a suspending agent and water dispersible granules is higher than that of some traditional formulations such as granules, water aqua and the like. Although the formulations can increase the water solubility of the original pesticide and enhance the pesticide effect, a large amount of organic solvents are used in the formulation processing and use to pollute the environment, and the like, so that the environmental safety is not negligibly damaged. How to improve the effective utilization rate of the pesticide and realize the reduction and the synergism of the pesticide becomes a problem which needs to be solved urgently, and has important research significance.

Disclosure of Invention

The invention aims to overcome the defects of the prior art and provide a novel pesticide preparation and a preparation method thereof, and the solubilization of the pesticide is realized through the inclusion of azo series calixarene and the pesticide.

More specifically, the first aspect of the present invention relates to a pesticidal formulation containing a pesticidal active ingredient and a calixarene of azo series.

The second aspect of the present invention relates to the above-mentioned pesticide preparation, wherein the calixarene of the azo series is represented by the following general formula:

R₂independently a hydrogen atom or a saturated or unsaturated, substituted or unsubstituted hydrocarbon group, R₁Are inorganic acid groups or organic acid groups as hydrophilic groups and their corresponding acid salts.

A third aspect of the present invention relates to the above-mentioned pesticidal formulation, wherein the hydrophilic moiety of the calixarene is an inorganic group including a sulfonic acid group, a phosphonic acid group, an amino group and the corresponding acid salt thereof, and the like.

The fourth aspect of the present invention relates to the above-mentioned pesticide preparation, wherein the hydrophilic portion of the calixarene is an organic acid group including a carboxyl group, a polyethylene glycol and a taurine group and the corresponding acid salt thereof, and the like.

A fifth aspect of the present invention relates to the above-mentioned pesticide preparation, wherein the pesticidal active ingredient comprises a herbicide, a plant growth regulator, a fungicide or an insecticide.

The sixth aspect of the present invention relates to the above-mentioned pesticide preparation, wherein the pesticide active ingredient comprises a herbicide, a plant growth regulator, a fungicide or an insecticide having at least one aromatic ring and four aromatic rings or less.

A seventh aspect of the present invention relates to a method for producing the above-mentioned pesticidal formulation, which comprises a step of mixing a dissolved pesticidal active ingredient and calixarene.

The pesticide preparation has good water solubility by bonding the calixarene and the pesticide active ingredient.

The pesticide preparation of the present invention is characterized in that the pesticide preparation contains a pesticide active ingredient and an azo series calixarene.

The pesticidal active ingredient contained in the pesticidal formulation of the present invention is not particularly limited as long as it can form a bond with an azo series calixarene. Useful pesticidal active ingredients are herbicides, plant growth regulators, bactericides or insecticides and the like, including geometric isomers, optical isomers and the like thereof. Preferred components are those having aromatic rings and a clathrate bond constant in the order of 3 to 7.

Active substance

Examples of herbicides and plant growth regulators are the known active substances which act as inhibitors of: acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthase, hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, and are described, for example, in Weed Research 26(1986) 441-.

More specifically, examples include the following active substances (compounds are described under "common names" according to the international organization for standardization (ISO) or under their chemical names or code numbers). In addition, the examples always encompass all application forms such as acids, salts and esters, and isomers, including variations such as stereoisomers and optical isomers. Examples of at least one application form and/or variant are given below:

acetochlor, acibenzolar-S-methyl, aclonifen-sodium, aclonifen, fenoxycarb, methomyl, metolcarb-K, aminopyralid, mesoxyfen, ammonium sulfamate, cyprodinil, anilofos, asulam, atrazine, oxadiazon, tetrazolsulfuron, azifop-N, beflubutamid, benazolin, benazolidone, flurtamone, flumetsulam, bensulfuron-methyl, bentazone, bensulfuron-methyl, benzobicyclon, benzobicyclopyrone, pyrazathion, bialaphos, bispyribac-sodium, bispyribac-methyl, bromacibenzoxim, bromacibenzol, carfentrazone, benazolin, fenthiuron, fenflurazone, fenphos, bencarb, concomitantly with bensulfuron, bromosulfuron, buminafos, tralkoxydim, butachlor, butafenacil, butachlor, dimethenamid, butoxycyclon, terbufen, cafenstrole, carfentrazone-ethyl, ethyl triazosulfuron, metoclopramide, mefenpyr, pyraclofen-ethyl, butylpyrachlor, chlorobromon, cloropham, varparvax-sodium, oatmeal, clofluoren, methylchlorofluoren, chlorphenamine, chlorimuron, ethylchlorimuron, chlormequat, cumquat ether, chlorophthalimide (chlorophthaleimide), dimethylchlorophthalic acid, chlorotoluron, chlorsulfuron, indolone, etholone, simetryn, cinosulfuron, clethodim, clodinafop-ethyl, pyridaphylzine, clomazone, isoxaflutole, clofenpropyzamide, clomeprop, dichlormid, penam, metosulam, cuaminosulfan, metosulam, bensulfuron-methyl, bensulfuron-methyl, bensulfuron-methyl, bensulfuron-methyl, benoxanil-methyl, benoxanil, benfurbenfurbenfurin, benfurin, benfurbenoxanil, benoxanil, cyprodinil, oxamate, tembotrione, thiopyrad, cyhaloron, cyhalofop-butyl, mefenpyr, cyproteron, tricyclodecane, 2,4-D, 2,4-DB, triflusuron, dalapon, butyryl hydrazine, dazomet, norflurazon, desmetryn, danshino-benzole (DTP), dodine, dicamba, dichlobenil, 2, 4-dichlopropionic acid, dichlorvon (diclofop), diclofop (diclofomethyl), diclofop-P-methyl, diclosulam, alachlor, acetomethenamine, cumarone, paraquat, diflufenican, diflufenzopyr, naftate, furazolon, dimeglunide, dimethenamid, isoethachlor, dimethenamid, pyrazone, pyraclonil, thiflufen-ethyl, metol, thiflufen-ethyl, meton, metoclopramide, thiflufen-ethyl, thiflufen, fenfluridone, bensulfuron-ethyl, benazol-methyl, benazol, benazolidone, benazol, benazolin, benazolidone, benazolin, benazolidone, benazolin, benone, benazolin, benone, benazolin, thiuron, benazolin, benone, thiuron, benazol, Dinotefuran, dinonyl ruthenate, diphenoyl-amine, ipratropium, diquat dibromide, fluroxypyr, diuron, DNOC, metribuzin, endothal, EPTC, dicamba, fluazifop, ethametsulfuron, metsulfuron-methyl, ethephon, thifensulfuron-methyl, oxazasulfuron, ethoxyfurazon, lactofen-ethyl, ethoxysulfuron, ethoxybenclamide, F-5331 namely N- [ 2-chloro-4-fluoro-5- [4- (3-fluoropropyl) -4, 5-dihydro-5-oxo-1H-tetrazol-1-yl ] phenyl ] -ethanesulfonamide, F-7967 namely 3- [ 7-chloro-5-fluoro-2- (trifluoromethyl) -1H-benzimidazol-4-yl ] -1-methyl-6- (trifluoromethyl) pyrimidine-2, 4- (1H,3H) -dione, 2,4, 5-aldicacid, fenoxaprop-P-ethyl, isoxaprop-P-ethyl, tebuconazole, fensulfuron-methyl, imazalil-M-isopropyl, imazalil-M-methyl, flazasulfuron, florasulam, fluazifop-butyl, isoprox-p-ethyl, fluoroketosulfuron-methyl, fluoropyrosulfuron-methyl, flumethazine, flufenacet, flupyridaphron-ethyl, flurazofam, flumetsulam, flumetol, flumetsulam, fururon, trifluofen, fluoroglycofen-ethyl, fluridofen-ethyl, tebufenon, trifluofen-ethyl, fluridofen-ethyl, tebufenon, tebufenofen-ethyl, tebufenon, tebuf, Flubenconazole, primisulfuron-methyl, fluoropropionic acid, flupyrsulfuron-methyl, flufenamic, carboxyfluoren-butyl, fluazinone, flurochloridone, fluroxypyr-meptyl, flurprimidol, flurtamone, oxazine oxalate, oxazine methyl ester, flufenacet, fomesafen, foramsulfuron, forchlorfenuron, clomiphos, furyloxyfen, glufosinate-ammonium, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate-isopropylammonium, H-9201 i.e.O- (2, 4-dimethyl-6-nitrophenyl) -O-ethyl-isopropylafosfamide, halosafen, halosulfuron-methyl, haloxyfop-P, halosulfuron-methyl, haloxyfen-methyl, haloxyfop-P, halosulfuron-P-methyl, halosulfuron-methyl, haloxyfop-P, haloxyfop, halosulfuron-P, haloxyfop, haloxynil, fluroxypwherein, Haloxyfop-ethoxyethyl ester, haloxyfop-P-ethoxyethyl ester, haloxyfop-methyl ester, haloxyfop-P-methyl ester, hexazinone, HW-02 i.e. 1- (dimethoxyphosphoryl) -ethyl- (2, 4-dichlorophenoxy) acetate, imazamox-methyl ester, imazethapyr-ammonium, imazapic, imazapyr-isopropylammonium, imazaquin-ammonium, imazethapyr-ammonium, imadazomethoa, trinexazole, indamine, triazineone, indol-3-ylacetic acid (IAA), 4-indol-3-ylbutanoic acid (IBA), iodosulfuron-methyl-sodium, thienylsulfone, thionine, imazachlor-methyl ester, imazapyr-P, imazapyr ester, imazapyr-P, imazapyr, imazapic acid, imazapyr, imazapic acid, imazapic acid, imazapic, Thiophenesulfone-sodium, iobenonitrile, ebecarbazone, butanamide, isodonalin, isoproturon, isolocuron, isometamifop, isoxaflutole, isoxadifen, KUH-043 i.e. 3- ({5- (difluoromethyl) -1-methyl-3- (trifluoromethyl) -1H-pyrazol-4-yl ] methyl } sulfonyl) -5, 5-dimethyl-4, 5-dihydro-1, 2-oxazole, tetramine, ketospiradox, lactofen, cyclamenine, linuron, maleohydrazide, MCPA, MCPB-methyl (MCPB-methyl), MCPB-ethyl (MCPB-ethyl) and MCPB-sodium, 2-methyl-4-chloropentyloxypropionic acid sodium, isoproturon, clomazone, isoxadifenoxide, isoxaflutole, isoxate, isoxadifen, isoxae, isoxadifen-methyl-4-methyl-4-chloropentyloxypropionic acid, and MCPB-methyl-4-methyl-4-methyl-4-methyl-p-, 2-methyl-4-chloropentyloxypropionic acid-butyl ester, 2-methyl-4-chloropentyloxypropionic acid-P-dimethylammonium, 2-methyl-4-chloropentyloxypropionic acid-P-2-ethylhexyl ester, 2-methyl-4-chloropentyloxypropionic acid-P-potassium, mefenacet, fluorosulfonamide, mepiquat chloride, mesosulfuron-methyl, mesotrione, methabenzthiazuron, metam, metamitron, metazachlor, diether clopyrazosulfuron, imazalil, methisulfuron, isoxathiuron, tralkoxydim, meton, 1-methylcyclopropaneon, metolachlor, metolachlorethamine, metolachlor, methimazole, methimazone, metosulfuron, metosulam, 1-methyl cyclopropane, metosulam, and a, metosulam, and a, metosulam, and a, metosulam, and, Methyl isothiocyanate, metoxuron, bromuron, metolachlor, S-metolachlor, metoxuron, metribuzin, metsulfuron-methyl, molinate, heptanolachlor, monourea dihydrosulfate, monosulfuron-methyl ester, metoxuron, MT128, i.e. 6-chloro-N- [ (2E) -3-chloroprop-2-en-1-yl ] -5-methyl-N-phenylpyridazin-3-amine, MT-5950, i.e. N- [ 3-chloro-4- (1-methylethyl) -phenyl ] -2-methylpentane amide, NGGC-011, napropamide, alachlor, imazamox, NC310, i.e. 4- (2, 4-dichlorobenzoyl) -1-methyl-5-benzyloxy pyrazole-amide, Bensulfuron-methyl, nicosulfuron, diclofen, asulam, benazolin, benfuresate, aclonifen, sodium nitrophenolate (isomer mixture), trifluoromethoxyfen, pelargonic acid, dacrofury, prosulfocarb, oxadiargyl, oxasulfuron, oxadiargyl, oxyfluorfen, paclobutrazol, paraquat dichloride, pelargonic acid (nonanic acid), pendimethalin, pendalin, penoxsulam, metolachlor, pentoxydim, bentazoxyfen, dimethenan, phenmedipham-ethyl, phenmedipham, flupyrazam, pinoxaden, pyraclonil, pyriphenop, pyripyrophylloton-butypro, pretilachlor, methylfluuron-methyl, metrafenone-methyl, probenazole, flumetsulam, propiconazole, propaquizamide, propaquizachlor, pyraclonil, calcium cyhalonil, propaquinone, propaquinol, bensulam, clorac, and other, etc, Jasmone, prometryn, propaferin, propanil, propaquizafop, anilazine, propisochlor, prosulfuron sodium, primisulfuron-methyl, pentyne, methidathion, prosulfocarb, prosulfuron, propyzamide, pyraclonil, ethacricet-ethyl, pyrasul-fonole, pyraclostrobin, pyrazosulfuron-ethyl, pyribambenez, propyribac-methyl, pyribencarb, pyridate, pyribenbac-methyl, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, imazaquin, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-methyl, quizalofop-P-ethyl, quinoxalin, pyrithion, pyrimethanil, pyriminobac-methyl, pyrithion, pyriminobac-methyl, pyriminostrobin, pyributhiziram, pyriminostrobin, pyrithion-P-methyl, pyrithion-methyl, pyributhiziram, pyribensulfuron-methyl, pyribensulfuron-ethyl, pyribenazol, pyribensulfuron-methyl, pyribenazol, pyribensulfuron-P-ethyl, pyribenazol, pyribenazolin, pyribenazol, pyribenazolin, pyribenazol, pyribenazolin-P-ethyl, pyribenazolin-ethyl, pyribenazolin, pyribenzoxim, pyribenazolin, pyribenzoxim, pyribenazolin, pyribenzoxim, pyribenazolin, pyribenzoxim, pyribenazolin, pyribenzoxim, pyribenazolin, pyribenazol, Sebutyn, sethoxydim, siduron, simazine, simetryn, SN-106279 methyl- (2R) -2- ({7- [ 2-chloro-4- (trifluoromethyl) phenoxy ] -2-naphthyl } oxy) propionate, sulcotrione, diclocyn (CDEC), methylsulfonylmethylamine, sulfosulfuron, methylsulfuron acid, N- (phosphonomethyl) glycine trimethylsulfonium salt (glyphosate-trimethylsulfonium salt), sulfosulfuron, SW-065, SYN-523, SYP-249 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl-5- [ 2-chloro-4- (trifluoromethyl) phenyl ] -2-nitrobenzoate, SYP-300, 1- [7-fluoro-3-oxo-4- (prop-2-yn-1-yl) -3,4-dihydro-2H-1, 4-benzoxazin-6-yl ] -3-propyl-2-thioimidazoline-4, 5-dione (1- [7-fluoro-3-oxo-4- (prop-

2-yn-1-yl) -3, 4-dihydroxy-2H-1, 4-benzoxadin-6-yl ] -3-propyl-2-thioxoimidazolidin-4,5-dione), grazing amine, tebuthiuron, tetrachloronitrobenzene, tefurazone, tembotrione, norflurazone, terbufos, tebuthizalin, terbufagin, terbutol, terbuthylacet, terbuthylazine, terbutryn, methoxyfenacet, fluthiacet, thifensulfuron-methyl, thiadiazoliding, tebuconazole, ketoureafophen, ketoureafungen methyl, thifensulfuron-methyl, methasulfosulfuron, prosulfocarb, penoxsulam, topramezone, tralkoxydim, metribuzin, triasulfuron, triaziflam, triafenamidofen, triasulfuron, tribenuron, metosulam, chlorsulfuron, triclopyr, clorac, etc, Trifloxysulfuron sodium, trifluralin, triflusulfuron-methyl, triton, trinexapac-ethyl, triflusulfuron-methyl, tstedof, uniconazole-P, mefenpyr, ZJ-0862, i.e. 3, 4-dichloro-N- {2- [4, 6-dimethoxypyrimidin-2-yl) oxy ] benzyl } aniline

Examples of herbicides that can be used in the present invention are given below in each of the action mechanism categories.

acetyl-CoA carboxylase (ACCase) inhibitors

Aryloxy phenoxy propionic acid ACCase inhibitors: clodinafop-propargyl, cyhalofop-butyl, diclofop-methyl, fenoxaprop-ethyl and fluazifop-p-butyl

haloxyfop-R-methyl, propaquizafop-p-ethyl, fenoxaprop-p-ethyl, metamifop

Cyclohexanedione ACCase inhibitors: graminis, tralkoxydim, clethodim, cycloxydim, clethodim, sethoxydim, pyrodim, tralkoxydim

Phenylpyrazoline ACCase inhibitors: pinoxaden.

Acetolactate synthase (ALS) inhibitors

Sulfonylurea ALS inhibitors: amidosulfuron, azimsulfuron, methylbenzsulfuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, sulfometuron-methyl, ethametsulfuron, ethoxysulfuron, flazasulfuron, fluzasulfuron, foramsulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron, mesosulfuron, metsulfuron-methyl, nicosulfuron, epoxysulfuron, methylprimisulfuron, pyrazosulfuron, rimsulfuron, sulfosulfuron, thifensulfuron-methyl, triasulfuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron, sulfosulfuron, TH547, NC620, and

imidazolinone (ALS) inhibitors: imazapic, imazamox, imazapic, imazapyr, imazaquin, imazapic

Triazolopyrimidine ALS inhibitors: cloransulam-methyl, diclosulam, florasulam, flumetsulam, metosulam, penoxsulam

Pyrimidinyl salicylic acid ALS inhibitors: bispyribac-sodium, pyribenzoxim, pyrithiobac-sodium, pyriminobac-sodium, pyrithiobac-sodium

Triazolinone ALS inhibitors: sodium fluorosulfuron, propoxycarbazone, ketoureidofenthiuron.

Photosynthesis inhibitor (photosystem II)

Triazine type: ametryn, atrazine, cyanazine, diuron, isovaleryl, prometon, prometryn, simazine, simetryn, terbuthylazine, and atrazine

Triazinone type: hexazinone, metamitron, metribuzin

Triazolinone types: amicarbazone

Uracil types: herbicidal pyribendin, lenacil and terbacil

Pyridazinone type: chlorphenamine maleate

Phenyl carbamate type: benzicao and bendiocide

Urea type: chlorsulfuron, chlortoluron, chlorsulfuron, oxazolone, diuron, sikone, fenuron, fluometuron, isoproturon, clomazone, linuron, methabenzthiazuron, bromuron, metoxuron, monolinuron, glufosinate, cycluron, tebuthiuron

Amide type: propanil and vegetable weedicide

Nitrile type: bromophenol oxime, companion agricultural, iodobenzonitrile

Benzothiadiazine (benzothiazine) type: mexican pine

Phenylpyridazines of the type: da Cao Te, Da Cao Zhi.

Bipyridinium type: diquat and paraquat.

Protoporphyrinogen Oxidase (PPO) inhibitors

Diphenyl ether type: acifluorfen, bifenox, metoxyfen, fluoroglycofen, fomesafen,

halosafen, lactofen, oxyfluorfen, metoxyfen

Phenyl pyrazole type: isopropidium and pyraflufen-ethyl

N-phenylphthalimide type: indoxyl, fluoroelenic acid, flumioxazin

Thiadiazole type: oxazine oxalic acid methyl ester and thiadiazolidino

Oxadiazole type: oxadiazon and oxadiargyl

Triazolinone types: azadirachtin, carfentrazone-ethyl, methylsulfonylmethylamine

Oxazolidinedione type: pentoxazone

Pyrimidinedione type: bifenarimuron-methyl and butafenacil

And (3) the other: pyraclonil, flumetsulam and fluazifop-butyl.

Carotenoid biosynthesis inhibitors

PDS inhibitors

Pyridazinone type: dacaomi (D.Don)

Pyridine carboxamide type: diflufenican and picolinafen

And (3) the other: beflubutamid, fluazinone, fluorochloridone, flurtamone

2.4-HPPD inhibitors

Types of triones: mesotrione, sulcotrione, benzobicyclon, terfuratone

Isoxazole (Isoxazole) type: isoxaclomefone, isoxaflutole

Pyrazole type: bicotrione, pyraclostrobin and benzoxyfen

3. Inhibitors with unknown targets

Triazole type: "Fujiangqiang" for killing weeds

Isoxazolone type: clomazone

Diphenyl ether type: aclonifen.

EPSP synthase inhibitors

Glycine type: glyphosate and glyphosate trimethyl sulfate.

Type of phosphinic acid: glufosinate-ammonium, bialaphos.

Inhibitors of DHP biosynthesis

Carbamate type: huangcaoling.

Dinitroaniline type: flumetsulam, butralin, dimethomorph, butafluazin, oryzalin, pendimethalin, trifluralin

Types of phosphoramides: methylaminophosphor and butafosinate

Pyridine type: fluroxypyr and thiabendazole

Type of benzamide: propyzamide, grazing amine and propanil.

Mitotic/microtubule formation inhibitors

Carbamate type: chlorpropham, propham, and Carbamine.

Ultra-long chain fatty acid biosynthesis inhibitor

Chloroacetamide type: acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, metazachlor, metolachlor, dimethenamid, pretilachlor, propyzamide, propisochlor, methoxyfenacet

Types of acetamide: bifenacet, napropamide

Type of oxyacetamide: flufenacet and mefenacet

Tetrazolinone types: tebuconazole

And (3) the other: anilofos, cafenstrole, mepiquat chloride.

Cellulose biosynthesis inhibitor

Nitrile type: dichlobenil and Cyhalofop-p-butyl

Type of benzamide: isooxazamide

Triazole carboxamide type: flubenconazole

Type of quinoline carboxylic acid: quinclorac.

Uncoupling agents

Dinitrophenol type: DNOC, dinol, dinonyl rutinate.

Fatty acid elongation inhibitors (non-ACCase inhibition)

Thiocarbamates: butachlor (buthylate), mefenamate, prosulfocarb, EPTC, esprocarb, dichlord, prosulfocarb, dichlorvos, and the like

Type of dithiophosphate: phosphorus ground

Benzofuran type: fulvic acid and ethofumesate

Chlorocarbonic acid (chlorocarbonic acid) type: TCA, dalapon and sodium tetrafluoropropionate.

Auxin type herbicides

Phenoxy carboxylic acid types: chlorantraniliprole, 2,4-D, 2,4-DB, mechlorhydrite, MCPA, MCPB, MCPP

Benzoic acid type: dicamba, 2,3,6-TBA

Pyridine carboxylic acid type: clopyralid, fluroxypyr, picloram, triclopyr, quinclorac

And (3) the other: benazolin.

Auxin transport inhibitors

Naphthalate (Naptalamate) type: grass inhibition

Semicarbazone type: diflufenzopyr sodium salt.

Others (mechanism of action unknown)

Aryl amino propionic acid type: fluoro methyl ester and fluoro isopropyl ester of wheat straw

Pyrazolium type: yeyankuo

Type of organic arsenic: DSMA, MSMA

And (3) the other: bromobutyrolac, clofluoren, cinmethylin, prosulfuron, chlorsulfuron, meturon, metsulfuron-methyl, ethoxybencarb, clodinafop-methyl, clethodim, metam-sodium, propanil, oleic acid, pelargonic acid, pyributicarb.

Preferred herbicides include those comprising more than one aromatic ring, less than four aromatic rings, capable of forming some bond with the clathrate, or salts thereof. Preferred examples include mefenacet, fomesafen, oxyfluorfen and the like.

The pesticidal active ingredient contained in the sustained-release pesticide formulation of the present invention is not particularly limited, and examples of the fungicide include the following:

(1) ergosterol biosynthesis inhibitors, such as aldimorph, penconazole, bitertanol, bromuconazole, cyproconazole, chlorotriazolol, difenoconazole, diniconazole, dodecamorph acetate, epoxiconazole, etaconazole, fenarimol, fenbuconazole, fenhexamid, fenpropidin, fenpropimorph, fluquinconazole, flurprimidol, flusilazole, flutriafol, furconazole, furilazole, hexaconazole, imazalil, imibenconazole, metconazole, myclobutanil, naftifine, nuarimol, oxpoconazole, paclobutrazol, pefurazoate, penconazole, fenbuconazole, prochloraz, propiconazole, prothioconazole, pennywort, pyriproxyfen, simeconazole, spiroxazole, tebuconazole, bitrex, fentebufen, triadimefon, triadimenol, tridemorph, triflumizole, pyrad, flutriafolpet, fluazid, fluazinam, trifloxystrobin, triflumizole, trifluralin, thiuracilostazol, trifluralin, thiuracilostazol, thiuracil, Triticonazole, uniconazole, precision uniconazole, clenbuterol, voriconazole, 1- (4-chlorophenyl) -2- (1H-1,2, 4-triazol-1-yl) cycloheptanol, 1- (2, 2-dimethyl-2, 3-dihydro-1H-inden-1-yl) -1H-imidazole-5-carboxylic acid methyl ester, N' - {5- (difluoromethyl) -2-methyl-4- [3- (trimethylsilyl) propoxy ] phenyl } -N-ethyl-N-methylimide

Formamide, N-ethyl-N-methyl-N' - { 2-methyl-5- (trifluoromethyl) -4- [3- (trimethylsilyl) propoxy ] phenyl } imide formamide, O- [1- (4-methoxyphenoxy) -3, 3-dimethylbut-2-yl ] 1H-imidazole-1-carbothioic acid ester.

(2) Respiratory chain complex I or II inhibitors, for example Bixafen, boscalid, carboxin, fluomepanide, fluropyramid, flutolanil, fluxapyroxad, furametpyr, fenpyrazamine, isopyrazam (mixture of cis-epimeric racemate 1RS,4SR,9RS and trans-epimeric racemate 1RS,4SR,9SR), isopyrazam (trans-epimeric enantiomer 1R,4S,9S), isopyrazam (trans-epimeric enantiomer 1S,4R,9R), isopyrazam (cis-epimeric racemate 1RS,4SR,9RS), isopyrazam (cis-epimeric enantiomer 1R,4S,9R), isopyrazam (cis-epimeric 1S,4R,9S), mefenacet, carboxin, penthiopyrad, sedaxane, thifluzamide, 1-methyl-N- [2- (1,1,2, 2-tetrafluoroethoxy) phenyl ] -3- (trifluoromethyl) -1H-pyrazole-4-carboxamide, 3- (difluoromethyl) -1-methyl-N- [2- (1,1,2, 2-tetrafluoroethoxy) phenyl ] -1H-pyrazole-4-carboxamide, 3- (difluoromethyl) -N- [ 4-fluoro-2- (1,1,2,3,3, 3-hexafluoropropoxy) phenyl ] -1-methyl-1H-pyrazole-4-carboxamide, fluazinam, carboxin, fluazinam, and a, N- [1- (2, 4-dichlorophenyl) -1-methoxypropan-2-yl ] -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, 5, 8-difluoro-N- [2- (2-fluoro-4- { [4- (trifluoromethyl) pyridin-2-yl ] oxy } phenyl) ethyl ] quinazolin-4-amine, N- [9- (dichloromethylene) -1,2,3, 4-tetrahydro-1, 4-methanonaphthalen-5-yl ] -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, methods of making and using the same, N- [ (1S,4R) -9- (dichloromethylene) -1,2,3, 4-tetrahydro-1, 4-methanonaphthalen-5-yl ] -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, N- [ (1R,4S) -9- (dichloromethylene) -1,2,3, 4-tetrahydro-1, 4-methanonaphthalen-5-yl ] -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide.

(3) Respiratory chain complex III inhibitors, for example ametoctradin, amisulbrom, azoxystrobin, cyazofamid, dimoxystrobin, enestroburin, famoxadone, fenamidone, fenoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyribencarb, triclopyr, trifloxystrobin, (2E) -2- (2- { [6- (3-chloro-2-methylphenoxy) -5-fluoropyrimidin-4-yl ] oxy } phenyl) -2- (methoxyimino) -N-methylacetamide, (2E) -2- (methoxyimino) -N-methyl-2- (2- { [ ({ (1E) -1- [3- (trifluoromethyl) phenyl ] ethylidene } amino) oxy ] methyl } phenyl) acetamide, (2E) -2- (methoxyimino) -N-methyl-2- {2- [ (E) - ({1- [3- (trifluoromethyl) phenyl ] ethoxy } imino) methyl ] phenyl } acetamide, (2E) -2- {2- [ ({ [ (1E) -1- (3- { [ (E) -1-fluoro-2-phenylvinyl ] oxy } phenyl) ethylidene ] amino } oxy) methyl ] phenyl } -2- (methoxyimino) -N-methylacetamide, (2E) -2- {2- [ ({ [ (2E,3E) -4- (2, 6-dichlorophenyl) but-3-en-2-ylidene ] amino } oxy) methyl ] phenyl } -2- (methoxyimino) -N-methylacetamide ) -N-methylacetamide, 2-chloro-N- (1,1, 3-trimethyl-2, 3-dihydro-1H-inden-4-yl) pyridine-3-carboxamide, 5-methoxy-2-methyl-4- (2- { [ ({ (1E) -1- [3- (trifluoromethyl) phenyl ] ethylidene } amino) oxy ] methyl } phenyl) -2, 4-dihydro-3H-1, 2, 4-triazol-3-one, (2E) -2- {2- [ ({ cyclopropyl [ (4-methoxyphenyl) imino ] methyl } sulfanyl) methyl ] phenyl } -3-methoxyprop-2-enoic acid methyl ester, and, N- (3-ethyl-3, 5, 5-trimethylcyclohexyl) -3- (formylamino) -2-hydroxybenzamide, 2- {2- [ (2, 5-dimethylphenoxy) methyl ] phenyl } -2-methoxy-N-methylacetamide, (2R) -2- {2- [ (2, 5-dimethylphenoxy) methyl ] phenyl } -2-methoxy-N-methylacetamide.

(4) Mitotic and cell-division inhibitors, for example benomyl, carbendazim, benzimidazole, diethofencarb, ethaboxam, fluopicolide, fuberidazole, pencycuron, thiabendazole, thiophanate, zoxamide, 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4, 6-trifluorophenyl) [1,2,4] triazolo [1,5-a ] pyrimidine, 3-chloro-5- (6-chloropyridin-3-yl) -6-methyl-4- (2,4, 6-trifluorophenyl) pyridazine.

(5) Compounds capable of having a multi-part (multi-molity) action, such as bordeaux mixture, captafol, captan, chlorothalonil, copper hydroxide, copper naphthenate, copper oxide, copper oxychloride, copper sulfate, sulfanilamide, dithianon, dodine free base, ferbam, flutriafol, folpet, biguanidinium, bisguanidinium acetate, bisguanidinium octylamine, bisguanidinium octyphenylsulfonate, bisguanidinium triacetate, mancopper, mancozeb, maneb, metiram, zineb, oxine-copper, propamidine, propineb, sulfur and sulfur preparations containing calcium polysulfides, thiram, tolylfluanide, zineb, ziram.

(6) Compounds capable of inducing host defenses, such as benzothiadiazole, isotianil, probenazole, tiadinil.

(7) Amino acid and/or protein biosynthesis inhibitors, such as, for example, amitocin, blasticidin, cyprodinil, kasugamycin monohydrate hydrochloride, mepanipyrim, pyrimethanil, 3- (5-fluoro-3, 3,4, 4-tetramethyl-3, 4-dihydroisoquinolin-1-yl) quinoline.

(8) ATP production inhibitors, for example triphenyltin acetate, triphenyltin chloride, fentin chloride, silthiopham.

(9) Cell wall synthesis inhibitors, such as benthiavalicarb-isopropyl, dimethomorph, flumorph, iprovalicarb, mandipropamid, polyoxin (polyoxin), polyoxin (polyoxorim), validamycin A, valifenalate.

(10) Lipids and membrane synthesis inhibitors, such as biphenyl, dicyclopentadienyl, clonidine, edifenphos, hymexazol, iodopropynyl butylmethylamine acid ester (iodocarb), iprobenfos, isoprothiolane, propamocarb hydrochloride, propamocarb, pyrazophos, pentachloronitrobenzene, tetrachloronitrobenzene, tolclofos-methyl.

(11) Melanin biosynthesis inhibitors such as cyprodinil, diclorocyanide, cyanamide, tetrachlorophthalide, pyroquilon, tricyclazole, 2,2, 2-trifluoroethyl { 3-methyl-1- [ (4-methylbenzoyl) amino ] butan-2-yl } carbamate.

(12) Inhibitors of nucleic acid synthesis, for example benalaxyl, benalaxyl-M (chiralaxyl), bupirimate, pyrimethanil, and, pyrimethanil, and their, pyrimethanil, and their, pyrimethanil, and their salts, and their, and their derivatives, and their salts, and their derivatives,

clozylacon, dimetachlor, diethylstilbestrol, furalaxyl, hymexazol, metalaxyl, efficient frost (degummed frost), furosemide, oxadixyl and quinconazole.

(13) Signal transduction inhibitors, for example ethiprole, fenpiclonil, fludioxonil, iprodione, procymidone, phenoxyquinoline, vinclozolin.

(14) Compounds capable of acting as uncouplers, such as binapacryl, dinocap, azozone, fluazinam, demodex.

(15) Other compounds, for example, benthiavalicarb, besoxazine, carbachol, carvone, chlorfenapyr, clofendone (chlazafenone), thiabendazole, cyflufenamid, cymoxanil, boscalid, dazomet, prochloraz, dichlorophen, pyridaben, difenzoquat methyl sulfate, diphenylamine, ecoate, fenpyrazamine, flutolanil, fluocinonide, flusulfamide, fluvalinate, fluthianil, fosetyl-aluminum, fosetyl-calcium, sodium fosinate, hexachlorobenzene, interphenomycin, sulbencarb, methyl isothiocyanate, metrafenone, milomycin, polymamycin, thiram, phthalein, octopirox, oxamyl, pentachlorophenol and salts thereof, phenothrin, phosphorous acid and salts thereof, propamocarb ethylphosphonate, nonproprione-sodium, propoxymine, pyrimorph, (2E) -3- (4-tert-butyl) -3- (2-4-tert-butyl-pyridyl) -4- (4-chloro-pyridyl) -1-4-butyl-4-pyridyl) -1-chloro-phenyl-4-phenyl-N-2-N-2-N-2-N-2-N-2-N-2-N-2-N-2-N-2-N-2-N-2-N -yl) prop-2-en-1-one, (2Z) -3- (4-tert-butylphenyl) -3- (2-chloropyridin-4-yl) -1- (morpholin-4-yl) prop-2-en-1-one, nitropyrrolidin, isobutoxyquinoline, biscumylphthalate, methanesulfonamide, imidazoxazine, trichlamide, cyanamide, (3S,6S,7R,8R) -8-benzyl-3- [ ({3- [ (isobutyryloxy) methoxy ] -4-methoxypyridin-2-yl } carbonyl) amino ] -6-methyl-4, 9-dioxo-1, 5-dioxonon-7-yl-2-methylpropionate, salts of these compounds, and their use in the preparation of pharmaceutical compositions, 1- (4- {4- [ (5R) -5- (2, 6-difluorophenyl) -4, 5-dihydro-1, 2-oxazol-3-yl ] -1, 3-thiazol-2-yl } piperidin-1-yl) -2- [ 5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl ] ethanone, 1- (4- {4- [ (5S) -5- (2, 6-difluorophenyl) -4, 5-dihydro-1, 2-oxazol-3-yl ] -1, 3-thiazol-2-yl } piperidin-1-yl) -2- [ 5-methyl-3- (trifluoromethyl) -1H-pyrazol- 1-yl ] ethanone, 1- (4- {4- [5- (2, 6-difluorophenyl) -4, 5-dihydro-1, 2-oxazol-3-yl ] -1, 3-thiazol-2-yl } piperidin-1-yl) -2- [ 5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl ] ethanone, 1- (4-methoxyphenoxy) -3, 3-dimethylbutan-2-yl-1H-imidazole-1-carboxylate, 2,3,5, 6-tetrachloro-4- (methylsulfonyl) pyridine, 2, 3-dibutyl-6-chlorothieno [2,3-d ] pyrimidin-4 (3H) -one, 2, 6-dimethyl-1H, 5H- [1,4] -dithiino [2,3-c:5,6-c' ] dipyrrole-1, 3,5,7(2H,6H) -tetraone, 2- [ 5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl ] -1- (4- {4- [ (5R) -5-phenyl-4, 5-dihydro-1, 2-oxazol-3-yl ] -1,3-1, 3-thiazol-2-yl } piperidin-1-yl) ethanone, 2- [ 5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl ] -1- (4- {4- [ (5S) -5-phenyl-4, 5-dihydro-1, 2-oxazol-3-yl ] -1, 3-thiazol-2-yl } piperidin-1-yl) ethanone, 2- [ 5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl ] -1- (4- {4- [ 5-phenyl-4, 5-dihydro-1, 2-oxazol-3-yl ] -1, 3-thiazol-2-yl } piperidin-1-yl) ethanone, 2-butoxy-6-iodo-3-propyl-4H-chromen-4-one, c-t, 2-chloro-5- [ 2-chloro-1- (2, 6-difluoro-4-methoxyphenyl) -4-methyl-1H-imidazol-5-yl ] pyridine, 2-phenylphenol and salts thereof, 3- (4,4, 5-trifluoro-3, 3-dimethyl-3, 4-dihydroisoquinolin-1-yl) quinoline, 3,4, 5-trichloropyridine-2, 6-dicarbonitrile, 3- [5- (4-chlorophenyl) -2, 3-dimethyl-1, 2-oxazolidin-3-yl ] pyridine, 3-chloro-5- (4-chlorophenyl) -4- (2, 6-difluorophenyl) -6-methylpyridazine, 4- (4-chlorophenyl) -5- (2, 6-difluorophenyl) -3, 6-dimethylpyridazine, 5-amino-1, 3, 4-thiadiazole-2-thiol, 5-chloro-N '-phenyl-N' - (prop-2-yn-1-yl) thiophene (thiophenone) -2-sulfonylhydrazide, 5-fluoro-2- [ (4-fluorobenzyl) oxy ] pyrimidin-4-amine, 5-fluoro-2- [ (4-methylbenzyl) oxy ] pyrimidin-4-amine, 5-methyl-6-octyl [1,2,4] triazolo [1,5-a ] pyrimidin-7-amine, and pharmaceutically acceptable salts thereof, (2Z) -3-amino-2-cyano-3-phenylprop-2-enoic acid ethyl ester, N' - (4- { [3- (4-chlorobenzyl) -1,2, 4-thiadiazol-5-yl ] oxy } -2, 5-dimethylphenyl) -N-ethyl-N-methylimidamide carboxamide, N- (4-chlorobenzyl) -3- [ 3-methoxy-4- (prop-2-yn-1-yloxy) phenyl ] propionamide, N- [ (4-chlorophenyl) (cyano) methyl ] -3- [ 3-methoxy-4- (prop-2-yn-1-yloxy) phenyl ] propionamide, and salts thereof, N- [ (5-bromo-3-chloropyridin-2-yl) methyl ] -2, 4-dichloropyridine-3-carboxamide, N- [1- (5-bromo-3-chloropyridin-2-yl) ethyl ] -2-fluoro-4-iodopyridine-3-carboxamide, N- { (E) - [ (cyclopropylmethoxy) imino ] [6- (difluoromethoxy) -2, 3-difluorophenyl ] methyl } -2-phenylacetamide, N- { (Z) - [ (cyclopropylmethoxy) imino ] [6- (difluoromethoxy) -2, 3-difluorophenyl ] methyl } -2-phenylacetamide, N' - {4- [ (3-tert-butyl-4-cyano-1, 2-thiazol-5-yl) oxy ] -2-chloro-5-methylphenyl } -N-ethyl-N-methylimidamide carboxamide, N-methyl-2- (1- { [ 5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl ] acetyl } piperidin-4-yl) -N- (1,2,3, 4-tetrahydronaphthalen-1-yl) -1, 3-thiazole-4-carboxamide, N-methyl-2- (1- { [ 5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl ] acetyl } piperidin-4-yl) -N- [ (1R) -1,2,3, 4-tetrahydronaphthalen-1-yl ] -1, 3-thiazole-4-carboxamide, N-methyl-2- (1- { [ 5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl ] acetyl } piperidin-4-yl) -N- [ (1S) -1,2,3, 4-tetrahydronaphthalen-1-yl ] -1, 3-thiazole-4-carboxamide, pentyl {6- [ ({ [ (1-methyl-1H-tetrazol-5-yl) (phenyl) methylene ] amino } oxy) methyl ] pyridine-2- -carbamate, phenazine-1-carboxylic acid, quinolin-8-ol sulfate (2:1), tert-butyl {6- [ ({ [ (1-methyl-1H-tetrazol-5-yl) (phenyl) methylidene ] amino } oxy) methyl ] pyridin-2-yl } carbamate.

(16) Still other compounds, for example 1-methyl-3- (trifluoromethyl) -N- [2' - (trifluoromethyl) biphenyl-2-yl ] -1H-pyrazole-4-carboxamide, N- (4' -chlorobiphenyl-2-yl) -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, N- (2',4' -dichlorobiphenyl-2-yl) -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, 3- (difluoromethyl) -1-methyl-N- [4' - (trifluoromethyl) biphenyl-2-yl ] -1H-pyrazole-4-carboxamide, n- (2',5' -difluorobiphenyl-2-yl) -1-methyl-3- (trifluoromethyl) -1H-pyrazole-4-carboxamide, 3- (difluoromethyl) -1-methyl-N- [4' - (prop-1-yn-1-yl) biphenyl-2-yl ] -1H-pyrazole-4-carboxamide, 5-fluoro-1, 3-dimethyl-N- [4' - (prop-1-yn-1-yl) biphenyl-2-yl ] -1H-pyrazole-4-carboxamide, 2-chloro-N- [4' - (prop-1-yn-1-yl) biphenyl-2-yl ] pyridine-3- Carboxamide, 3- (difluoromethyl) -N- [4'-3, 3-dimethylbut-1-yn-1-yl) -biphenyl-2-yl ] -1-methyl-1H-pyrazole-4-carboxamide, N- [4' - (3, 3-dimethylbut-1-yn-1-yl) biphenyl-2-yl ] -5-fluoro-1, 3-dimethyl-1H-pyrazole-4-carboxamide, 3- (difluoromethyl) -N- (4 '-ethynylbiphenyl-2-yl) -1-methyl-1H-pyrazole-4-carboxamide, N- (4' -ethynylbiphenyl-2-yl) -5-fluoro -1, 3-dimethyl-1H-pyrazole-4-carboxamide, 2-chloro-N- (4 '-ethynylbiphenyl-2-yl) pyridine-3-carboxamide, 2-chloro-N- [4' - (3, 3-dimethylbut-1-yn-1-yl) biphenyl-2-yl ] pyridine-3-carboxamide, 4- (difluoromethyl) -2-methyl-N- [4'- (trifluoromethyl) biphenyl-2-yl ] -1, 3-thiazole-5-carboxamide, 5-fluoro-N- [4' - (3-hydroxy-3-methylbut-1-yn-1-yl) biphenyl-2-yl ] -1, 3-dimethyl-1H-pyrazole-4-carboxamide, 2-chloro-N- [4' - (3-hydroxy-3-methylbut-1-yn-1-yl) biphenyl-2-yl ] pyridine-3-carboxamide, 3- (difluoromethyl) -N- [4' - (3-methoxy-3-methylbut-1-yn-1-yl) -biphenyl-2-yl ] -1-methyl-1H-pyrazole-4-carboxamide, 5-fluoro-N- [4' - (3-methoxy-3-methylbut-1-yn-1-yl) biphenyl-2-yl ] -1, 3-dimethyl-1H-pyrazole-4-carboxamide, 2-chloro-N- [4' - (3-methoxy-3-methylbut-1-yn-1-yl) biphenyl-2-yl ] pyridine-3-carboxamide, (5-bromo-2-methoxy-4-methylpyridin-3-yl) (2,3, 4-trimethoxy-6-methylphenyl) methanone, N- [2- (4- { [3- (4-chlorophenyl) prop-2-yn-1-yl ] oxy } -3-methoxyphenyl) ethyl ] -N2- (methylsulfonyl) valinamide, 4-oxo-4- [ (2-phenylethyl) amino ] butyric acid, N-dimethylformamide, N-dimethylformamide, N, or N, is a salt, N, or N, each of a salt, N, each of 3, N, or N, each of a salt, in the salt, each of a salt of a compound, or N, in a compound, in a salt, or N, or a salt, or N, in a salt, or N, in a salt, or a salt, in a salt, or a salt, in a salt, or a salt, in a salt, or a salt, in a salt, or a salt, in a salt, or a salt, in a salt, or a salt, But-3-yn-1-yl {6- [ ({ [ (Z) - (1-methyl-1H-tetrazol-5-yl) (phenyl) methylidene ] amino } oxy) methyl ] pyridin-2-yl } carbamate.

The compounds classified into the above (1) to (16) may form a salt with a suitable base or acid as long as the functional group is acceptable.

Examples of the pesticide as the pesticidal active ingredient of the present invention include the following. The active ingredients described "by name" are known or described, for example, in Pesticide Manual ("The Pesticide Manual", 14 th edition, British Crop Protection Council 2006) or can be searched on The Internet (for example http:// www.alanwood.net/pesticides).

(1) Acetylcholinesterase (AChE) inhibitors, e.g. of the carbamate type, such as, for example, gossypol (II-1-1), aldicarb (II-1-2), bendiocarb (II-1-3), benfuracarb (II-1-4), carbosulfan (II-1-5), ketoprofen (II-1-6), carbaryl (II-1-7), carbofuran (II-1-8), carbosulfan (II-1-9), ethiofencarb (II-1-10), fenobucarb (II-1-11), varenidine (II-1-12), furamexane (II-1-13), isoprocarb (II-1-14), methiocarb (II-1-15), Methomyl (II-1-16), metolcarb (II-1-17), oxamyl (II-1-18), pirimicarb (II-1-19), propoxur (II-1-20), thiodicarb (II-1-21), monocarb (II-1-22), triazamate (II-1-23), trimethacarb (II-1-24), XMC (II-1-25), and methomyl (II-1-24)

Methiocarb (II-1-26); and organic phosphate types such as acephate (II-1-27), pirimiphos-methyl (II-1-28), oryphos-ethyl (II-1-29), oryphos-methyl (II-1-30), cadusafos (II-1-31), phosphorus oxychloride (II-1-32), chlorfenvinphos (II-1-33), chlormephos (II-1-34), chlorpyrifos (II-1-35), chlorpyrifos-methyl (II-1-36), coumaphos (II-1-37), cyanophos (II-1-38), oxydisulphonate (II-1-39), diazinon (II-1-40), dichlorvos/DDVP (II-1-41), chlorothalofop (II-1-42), dichlorphos (II-1-42), Dimethoate (II-1-43), methoprene (II-1-44), disulfoton (II-1-45), EPN (II-1-46), ethion (II-1-47), fenamiphos (II-1-48), vazaphos (II-1-49), fenamiphos (II-1-50), fenitrothion (II-1-51), fenthion (II-1-52), fosthiazate (II-1-53), heptenophos (II-1-54), imicyafos (II-1-55), isosaliphos (II-1-56), isopropyl O- (methoxyaminothiophosphoryl) salicylate (II-1-57), isoxazolaphos (II-1-58), Horse draws

Sulfur-phosphorus (II-1-59), aphis-killing (II-1-60), methamidophos (II-1-61), methidathion (II-1-62), metocloprid (II-1-63), monocrotophos (II-1-64), naled (II-1-65), omethoate (II-1-66), oxydol (II-1-67), parathion (II-1-68), methyl parathion (II-1-69), phenthoate (II-1-70), phorate (II-1-71), phoxim (II-1-72), phosmet (II-1-73), phosphamidon (II-1-74), phoxim (II-1-75), Chlorfenphos (II-1-76), profenofos (II-1-77), amicarbazone (II-1-78), profenofos (II-1-79), pyrazothion (II-1-80), pyridaphenthion (II-1-81), quinalphos (II-1-82), sulfotep (II-1-83), butylpyrimidine phosphine (II-1-84), disulfoton (II-1-85), terbufos (II-1-86), fenitrothion (II-1-87), methyl disulfate (II-1-88), triazophos (II-1-89), trichlorfon (II-1-90) and triazophos (II-1-91).

(2) GABA-controlled chloride channel antagonists, for example, cyclic diene organochlorine types such as chlordane (II-2-1), endosulfan (II-2-2); and phenylpyrazole types (fiprole types) such as ethiprole (II-2-3), fipronil (II-2-4).

(3) Sodium channel modulators/voltage-dependent sodium channel blockers, for example of the pyrethroid type, such as bifenthrin (II-3-1), allethrin (II-3-2), d-cis-trans allethrin (II-3-3), d-trans allethrin (II-3-4), bifenthrin (II-3-5), bioallethrin (II-3-6), bioallethrin S-cyclopentyl isomer (II-3-7), biocethofenprox (II-3-8), cycloprothrin (II-3-9), cyfluthrin (II-3-10), beta-cyfluthrin (II-3-11), cyfluthrin (II-3-12), Lambda-cyhalothrin (II-3-13), gamma-cyhalothrin (II-3-14), cypermethrin (II-3-15), alpha-cypermethrin (II-3-16), beta-cypermethrin (II-3-17), theta-cypermethrin (II-3-18), zeta-cypermethrin (II-3-19), cyphenothrin [ (1R) -trans isomer (] II-3-20), deltamethrin (II-3-21), empenthrin [ (EZ) - (1R) isomer (] II-3-22), esfenvalerate (II-3-23), ethofenprox (II-3-24), fenpropathrin (II-3-25), Fenvalerate (II-3-26), flucythrinate (II-3-27), flumethrin (II-3-28), tau-flumethrin (II-3-29), benzyl mite ether (II-3-30), imiprothrin (II-3-31), kadethrine (II-3-32), permethrin (II-3-33), phenothrin [ (1R) -trans isomer (] II-3-34), Dexpanthemum propargyl ester (II-3-35), pyrethrin (II-3-36), Mexican chrysanthemum (II-3-37), silafluofen (II-3-38), tefluthrin (II-3-39), tetramethrin (II-3-40), Tetramethrin [ (1R) -isomer (] II-3-41), tetrabromoethrin (II-3-42), transfluthrin (II-3-43); and DDT (II-3-44); and methoxy chloride (II-3-45).

(4) Nicotinic acetylcholine receptor (nAChR) antagonists, for example of the neonicotinoid type, such as acetamiprid (II-4-1), clothianidin (II-4-2), dinotefuran (II-4-3), imidacloprid (II-4-4), nitenpyram (II-4-5), thiacloprid (II-4-6), thiamethoxam (II-4-7); and nicotine (II-4-8).

(5) Nicotinic acetylcholine receptor (nAChR) allosteric activators, e.g., spinosyn types, such as spinetoram (II-5-1), spinosyn (II-5-2).

(6) Chlorine channel activators, for example of the avermectin/acaricidal type, such as avermectin (II-6-1), emamectin benzoate (II-6-2), lepimectin (II-6-3), milbemectin (II-6-4).

(7) Juvenile hormone analogs, for example juvenile hormone analog types such as hydroprene (II-7-1), methoprene (II-7-2), methoprene (II-7-3); and fenoxycarb (II-7-4); and pyriproxyfen (II-7-5).

(8) Other non-specific (multi-part) inhibitors, for example alkyl halides such as methyl bromide (II-8-1), other alkyl halides; and chloropicrin (II-8-2), sulfuryl fluoride (II-8-3); and borax (II-8-4); and antimony potassium tartrate (II-8-5).

(9) Selective antifeedants, such as pymetrozine (II-9-1); and flonicamid (II-9-2).

(10) Mite growth inhibitors such as clofentezine (II-10-1), hexythiazox (II-10-2), flutenzine (II-10-3); and etoxazole (II-10-4).

(11) Destructive microorganisms of insect digestive tract membranes, such as Bacillus thuringiensis subsp

(II-11-2), Bacillus thuringiensis subsp.aizawai (II-11-3), Bacillus thuringiensis subsp.kurstaki (II-11-4), Bacillus thuringiensis subsp.tenebriensis (II-11-5), BT crop protein: cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3Ab, Cry3Ab, Cry3Bb, Cry34/35Ab1 (II-11-6).

(12) Mitochondrial ATP synthase inhibitors, such as diafenthiuron (II-12-1); and organotin acaricides such as azocyclotin (II-12-2), tricyclotin (II-12-3), fenbutatin (II-12-4); and propargite (II-12-5); and Tetrachlorfenapyr sulfone (II-12-6).

(13) Oxidative phosphorylation uncouplers activated by blocking proton concentration gradients, such as chlorfenapyr (II-13-1), DNOC (II-13-2), fluben (II-13-3).

(14) Nicotinic acetylcholine receptor (nAChR) channel inhibitors, such as dimehypo (II-14-1), cartap (II-14-2), thiocyclam (II-14-3), bisultap (II-14-4).

(15) Chitin biosynthesis inhibitors of type 0, e.g. bistrifluron (II-15-1), chlorfluazuron (II-15-2),

Diflubenzuron (II-15-3), epoxiconazole (II-15-4), flufenoxuron (II-15-5), hexaflumuron (II-15-6), lufenuron (II-15-7), novaluron (II-15-8), noviflumuron (II-15-9), teflubenzuron (II-15-10) and triflumuron (II-15-11).

(16) Chitin biosynthesis inhibitors, type 1, such as buprofezin (II-16-1).

(17) Ecdysone interferons (Ecdysis disruptors), such as cyromazine (II-17-1).

(18) Ecdysone receptor antagonists such as chromafenozide (II-18-1), chromafenozide (II-18-2), methoxyfenozide (II-18-3), tebufenozide (II-18-4).

(19) Octopamine receptor antagonists, such as amitraz (II-19-1).

(20) Mitochondrial complex III electron transport inhibitors such as hydramethylnon (II-20-1); and acequinocyl (II-20-2); and fluacrypyrim (II-20-3).

(21) Mitochondrial complex I electron transport inhibitors, for example METI acaricides, such as fenazaquin (II-21-1), fenpyroximate (II-21-2), pyriminostrobin (II-21-3), pyridaben (II-21-4), tebufenpyrad (II-21-5), tolfenpyrad (II-21-6); and rotenone (derris) (II-21-7).

(22) Voltage-dependent sodium channel blockers, such as indoxacarb (II-22-1); and metaflumizone (II-22-2).

(23) acetyl-CoA carboxylases, for example tetronic acid, strong acid derivatives of muricid, such as spirodiclofen (II-23-1), spiromesifen (II-23-2) and spirotetramat (II-23-3).

(24) Mitochondrial complex IV electron transport inhibitors, for example phosphines, such as aluminum phosphide (II-24-1), calcium phosphide (II-24-2), phosphine (II-24-3), zinc phosphide (II-24-4); and cyanide (II-24-5).

(25) Mitochondrial complex II electron transport inhibitors, such as cyenopyrafen (II-25-1).

(28) Ryanodine receptor modulators, for example diamides, such as chlorantraniliprole (II-28-1), fulvenediamide (II-28-2).

(29) Other active substances with unknown or uncertain action mechanism, such as sulfadiazine (II-29-1), azadirachtin (II-29-2), benclothiaz (II-29-3), fenpyroximate (II-29-4), fenpyroximate (II-29-5), fenisobromolate (II-29-6), mefenmanam (II-29-7), cryolite (II-29-8), cyantranilide (cyazypyr) (II-29-9), cyflumetofen (II-29-10), dicofol (II-29-11), flufenzine (II-29-12), fluensulfone (II-29-13), pyrimethanil (II-29-14), butaronil (II-29-15), Fluopyram (II-29-16), furoxan (II-29-17), imidaclothiz (II-29-18), iprodione (II-29-19), meperfluthrin (II-29-20), pyridalyl (II-29-21), fluquindox (II-29-22), tefluthrin (II-29-23) and methyl iodide (II-29-24); other products derived from Bacillus firmus (Bacillus firmus), including those other than the strain CNCM I-1582, such as VoTivo and BioNem (II-29-25)

The solubility of the pesticidal active ingredient is not particularly limited, but is preferably slightly soluble in water or methanol (>1 mM).

Selective herbicidal effects between cultivated plants and weeds can be achieved by the pesticide formulations of the embodiments of the present invention. In this specification, weeds in the broad sense refer to any plant that grows in an undesirable place. For example, the pesticide preparation can be used for the following weeds and cultivated plants.

Genus of dicotyledonous weeds: mustard (Sinapis), shepherdspurse (Capsella), cress (Leipidium), mirabilis (Galium), chickweed (Stellaria), Chenopodium/Chenopodium (Chenopodium), Kochia (Kochia), nettle (Urtica), Adenophora/Ottelia/Senecio (Senecio), Chenopodium/Amaranthus (Amaranthus), Portulaca/sunflower (Portulaca), Ocimum (Xanthium), Pharbitidis (Ipomoea), Polygonum (Polygonum), ragulus (Ambrosia), Cirsium/Fusarium (Solanum), Sonchusa (Cirsium), Solanum/Solidago (Solanum)), Solanum (Solanum/Robinia), Polygonum (Polygonum), Solanum (Potentilla (Robinia), Solanum/Solanum (Rotunium), Solanum (Solanum/Rotunium), Solanum (Solarium (Solidago), Solanum/Robinia), Solanum (Solarium (Solidago), Sesamum indicum (Lamium), speranskia/avena canina (Veronica), stramonium (Datura), Viola (Viola), urtica (Galeopsis), poppy (Papaver), cornflower (Centaurea), achyranthes bidentata (galinoga), arthritic (Rotala), motherwort (Lindernia), Sesbania (Sesbania), white clover (pharifolium), Abutilon (Abutilon), Pharbitis (summertium), white mugwort (Matricaria), Artemisia (Artemisia), and the like.

Genus of dicotyledonous cultivated plants: cotton (Gossypium), soybean (Glycine), swiss beet/beet (Beta), carrot (Daucus), kidney bean/kidney bean (Phaseolus), pea (Pisum), eggplant/potato (Solanum), flax (Linum), sweet potato/trumpet flower (Ipomoea), broad bean/wild pea (Vicia), tobacco (Nicotiana), tomato (Lycopersicon), peanut (Arachis), rapeseed/cabbage/kohlrabi/cabbage (Brassica), ixeris sonchifolia (Lactuca), cucumber/melon (Cucumis), pumpkin (Cucurbita), etc.

Genus of monocotyledonous weeds: japanese barnyard grass (echinochloa), green bristlegrass/millet (Setaria), millet (Panicum), large crabgrass (Digitaria), sandCat's-Tail/timothy (phragmites), bluegrass/annual bluegrass (precocious grass (Poa)), fescue/small Festuca (fescue), goosegrass/switchgrass (cricke), toxylum (Lolium), kiskatsurada/flathead oat (brooms), common wild oat/oat (Avena), asian grass/sedge/rush/purple fringe (Cyperus), Sorghum (sorum), wheat (agrimony), bluegrass (agrimony (agrimonia), grassy (morinda), grassy/sargassum), etc. (sedge/sargassum), sargassum (sargassum), etc Arrowhead/trifoliate arrowhead (Sagittaria), chufa/water chestnut (Eleocharis), Scirpus/scitoi (Scirpus), Paspalum (Paspalum), duckbill (Ischaemum), glume snips (Agrostis), Alopecurus (Alopecurus), bermuda (Cynodon), dayflower (Commelina), Brachiaria (Brachiaria), moleplant (Leptochloa), etc.

Genus of monocotyledonous cultivated plants: rice (Oryza), maize/corn (Zea), wheat (Triticum), barley (Hordeum), common wild oat/oat (Avena), rye (Secale), Sorghum (Sorghum), millet (Panicum), sugarcane/waseobana (Saccharum), pineapple (Ananas), Asparagus (Asparagus), welsh onion/leek (Allium), etc.

The pesticide formulation of the present invention is not limited to use with these species of weeds, but is also applicable to other species of weeds.

An insecticide may be used as the pesticidal active ingredient contained in the pesticidal preparation of the present invention. The pesticidal formulation of one embodiment of the present invention exhibits an accurate control effect on harmful insects without causing chemical damage to cultivated plants. Furthermore, the pesticide formulation of the present invention can be used to control a wide variety of pests, such as harmful sap-sucking insects, chewing insects and other plant parasitic insects, and thus can be used to control and exterminate them.

Examples of such insects include the following.

Insecta includes:

coleopteran pests such as azure bean (Callosobruchus Chinensis), rice weevil (Sitophilus zeamais)), flour beetle (Tribolium castaneum), 28-star potato beetle (Epilachna virginiana), barley nematode (agrioticus bisporus), soybean beetle (soybean beetle), colorado potato beetle (leptinotara decemlineata), corn rootworm (Diabrotica spp)), yersinia funiculorum (Monochamus alternatus), rice weevil (lissorophyces sp), rice weevil (lissorophyces sp), and pink beetle (rice borer);

carp louse-type pests such as gypsy moth (Lymantria dispar), dried moth (Malacosia neustria)), cabbage butterfly (Pieri rapae cruvora), oriental armyworm (Spodoptera litura), cabbage looper (Mamestra brassicae), rice stem borer (Chilo supressalis), European corn borer (Ostrinia nubilalis), tropical fruit moth (Cadra cautala), tea leaf roller (Adenopsis), apple leaf roller (Cydia pomonella)), yellow cutworm (Agrocybe sempervirens (Agrocybe), large leaf roller (Gallothuria), tobacco leaf roller (Plutella), Plutella xylostella (Plutella xylostella), tobacco leaf (Heliotis virescens) and tobacco leaf (Heliothis virescens), tobacco leaf roller (Heliotis virescens);

hemipteran pests, such as black tail leafhopper (Nephotettix cincticeps), brown planthopper (Nilaparvata lugens), kang pink scale (kang pink scale) (Pseudococcus comstocki), arrowhead scale (Unaspis yanonensis)), peach aphid (Myzus persica)), apple yellow aphid (apple yellow aphid), cotton aphid (cotton aphid), mustard plant aphid (mustard aphid), pear reticulum bug (stephanis nashi), elephant (nezapra stinkbugs.), greenhouse pink plant (greenhouse aphids), and wood louse (xylaria);

pests of the order Thysanoptera, e.g. Thrips citrulli (Thrips palmi), Frankliniella occidentalis (Frankliniella occidentalis)

(Franklinella occidentalis))；

Orthoptera pests, such as mole cricket africana (Gryllotalpa africana), Locusta migratoria (Locusta migratoria);

pests of the order blattaria, such as german cockroaches (Blatella germanica), american cockroaches (american cockroaches), termites (Reticulitermes speratus), termites (coptotrmes formosanus);

diptera pests, such as common house flies (Musca domestica), yellow-fever mosquitoes (Aedes aegypti), soybean flies (Delia platura), Culex pipiens (Culex pipiens pallens), Anopheles chinensis (Anopheles sinensis), Aedes gibelii (Culex pipiens), Nephelus trifolius (Culex pipiens), and Liriomyza trifoliata (Liriomyza trifolii).

Further, examples of mites include Tetranychus cinnabarinus (Tetranychus cinannarinus), Tetranychus urticae (Tetranychus urticae), citrus red mites (pannychus citri), citrus rust mites (citrus rust (Aculops pelekassai)), dust mites (Tarsonemus spp.), and the like.

Further, examples of nematodes include, for example, sweetpotato root-knot nematodes (meloidogyneinica), pine wood nematodes (Bursaphelenchus xylophilus), strawberry curly-disease nematodes (strawberry curly-disease nematodes), soybean cyst nematodes (heterodera), root rot nematodes (Pratylenchus spp.), and the like.

The fungicide can be used as an agricultural chemical active ingredient contained in the agricultural chemical preparation of the present invention. The pesticide preparations are usually used as fungicides (fungicides) for a variety of plants which are attacked by Plasmodiophoromycetes (Plasmodiophoromycetes), Oomycetes (oomyces), Zygomycetes (zygomyycetes), Ascomycetes (Ascomycetes), Basidiomycetes (Basidiomycetes) and Deuteromycetes (Deuteromycetes). The pesticide preparation exhibits a particularly good control effect on plant pathogens such as Gibberella fujikuroi, Pyricularia oryzae, Cochliobacter uteri (Cochliobolus miyabenus), and the like.

In the present invention, the calixarene having an azo group is not particularly limited, but is preferably a calixarene represented by the following general formula:

R₂independently a hydrogen atom or a saturated or unsaturated, substituted or unsubstituted hydrocarbon group, R₁Is an inorganic acid group or an organic acid group as a hydrophilic group.

As the group having a hydrophilic moiety, a carboxyl group, a sulfonic acid group, a phosphonic acid group, an amino group and their corresponding acid salts are preferable. The calixarene n value is preferably 4,5, 6, 8. The azo series calixarenes form relatively stable bonds with pesticide active ingredients having more than one and less than four aromatic rings. The aromatic ring may contain a hetero atom or may be further substituted with a suitable substituent such as a halogen atom or the like. Specific examples of the aromatic ring include a benzene ring, a naphthalene ring, a pyrazole ring, a pyridine ring, a pyrrole ring, a quinoline ring, a toluidine ring, an indole ring, an imidazole ring and a pyrazine ring. Examples of the saturated or unsaturated hydrocarbon group include an alkyl group (cycloalkyl group, linear or branched alkyl group), an alkenyl group, an alkynyl group and an aryl group. Examples of substituents include halogen, atoms such as chlorine and bromine, phospho, sulfo, aldehyde, alkoxy, carbonyl, hydroxy, oxydialkyl, amino and ═ O. Examples of the above calixarenes include carboxyazo calix [4] arene, carboxyazo calix [5] arene, carboxyazo calix [6] arene, carboxyazo calix [8] arene, sulfoazo calix [4] arene, sulfoazo calix [5] arene, sulfoazo calix [6] arene, sulfoazo calix [8] arene, phosphonic acid azo calix [4] arene, phosphonic acid azo calix [5] arene, phosphonic acid azo calix [6] arene, phosphonic acid azo calix [8] arene, quaternary ammonium salt azo calix [4] arene, quaternary ammonium salt azo calix [5] arene, quaternary ammonium salt azo calix [6] arene, quaternary ammonium salt azo calix [8] arene, more preferably sulfoazo calix arene series, the molar ratio of calixarenes to the pesticide base being between 1 and 2.5. Furthermore, the calixarene is preferably used in the range of 0.01 to 10mol, particularly 1 to 3mol, per mol of the pesticidal active ingredient.

The pesticidal active ingredient is preferably a component which can be sparingly soluble (>1mM) in water or methanol.

The method for producing the pesticidal preparation of the present invention is not particularly limited, and a commonly used method for preparing an inclusion compound, including an ultrasonic method, an oscillation method, a grinding method, a freeze-drying method and the like, can heat the preparation, but the heating temperature needs to be controlled below the decomposition temperature of the pesticide.

The invention has the advantages and positive effects that:

the pesticide preparation of the present invention has the advantage of being capable of solubilization. The dosage of organic reagent in the pesticide preparation is greatly reduced, and the toxicity in organisms and soil can be reduced.

Detailed Description

The present invention is further illustrated by the following specific examples, which are intended to be illustrative, not limiting and are not intended to limit the scope of the invention.

In the following production examples, parts refer to molar parts.

Example 1

1.2 parts of sulfoazocalixarene (wherein R₂H, n is 4), 1 part hexaconazole Phosphate Buffered Saline (PBS) is placed in a reagent bottle to prepare 1mM PBS aqueous solution and shaken in a shaker overnight, and combined in a water bath at 40 ℃ for ultra-highSound for 2 hours.

Example 2

A Phosphate Buffered Saline (PBS) formulation was obtained by the same procedure as described in example 1, except that dimethomorph was used instead of hexaconazole in example 1, and sulfoazocalixarene was changed to 1.5 parts.

Example 3

A Phosphate Buffered Saline (PBS) formulation was obtained by the same procedure as described in example 1, except that hexaconazole in example 1 was replaced with quizalofop-p-ethyl, sulfoazocalixarene was changed to 1.5 parts, and the solution concentration was 0.5 mM.

Example 4

A Phosphate Buffered Saline (PBS) formulation was obtained by the same operation as described in example 1, except that sulfafurazone was used instead of hexaconazole in example 1, sulfoazocalixarene was changed to 2 parts, and the solution concentration was 0.5 mM.

Example 5

An aqueous solution preparation was obtained by the same operation as described in example 4, substituting ultrapure water for the PBS solution, and having a concentration of 0.5 mM.

Example 6

An aqueous solution formulation was obtained by the same operation as described in example 5, except that mefenacet was used in place of fomesafen in example 5, and the concentration of the solution was 0.5 mM.

Example 7

An aqueous solution formulation was obtained by the same operation as described in example 6, with the solution concentration changed to 1 mM.

Comparative example 1

A Phosphate Buffered Saline (PBS) formulation was obtained by the same procedure as described in example 1, except that calixarene was not added.

Comparative example 2

A Phosphate Buffered Saline (PBS) formulation was obtained by the same procedure as described in example 2, except that calixarene was not added.

Comparative example 3

A Phosphate Buffered Saline (PBS) formulation was obtained by the same procedure as described in example 3, except that calixarene was not added.

Comparative example 4

A Phosphate Buffered Saline (PBS) formulation was obtained by the same procedure as described in example 4, except that calixarene was not added.

Comparative example 5

An aqueous solution formulation was obtained by the same operation as described in example 5, except that no calixarene was added.

Comparative example 6

An aqueous solution formulation was obtained by the same operation as described in example 6, except that no calixarene was added.

Comparative example 7

An aqueous solution formulation was obtained by the same operation as described in example 7, except that no calixarene was added.

Test for verifying the influence of calixarene on the solubility of active ingredients in pesticides

Hexaconazole, dimethomorph, quizalofop-p-ethyl, fomesafen and mefenacet are respectively dissolved in methanol to prepare 10mM methanol solution, sulfoazo calix [4] arene (SAC4A) is used as a main body and rhodamine B (RhB) is used as a dye in a Phosphate Buffer Solution (PBS) system, and the bonding constant of pesticide molecules and calixarene is determined by IDA (dye fluorescence competitive titration method) and GDA (guest fluorescence competitive titration method), as shown in Table 1.

TABLE 1

Inclusion compound	Constant of bonding	Measurement method
			SAC4A-RhB	1.48*10^6±2.4*10^5	IDA
SAC4A-quizalofop-p-ethyl	1.76*10^5±1.48*10^4	IDA,GDA
			SAC 4A-Dimethomorph	2.10*10^5±1.36*10^4	IDA
SAC 4A-hexaconazole	3.51*10^5±4.33*10^3	IDA
			SAC 4A-mefenacet	1.26*10^5±3.46*10^4	GDA
SAC 4A-fomesafen	9.90*10^4±7.07*10^3	GDA

Table 1 shows the formation of the linkage of the pesticidal active ingredient to the sulfoazocalixarene.

The results of the dissolution test in water are shown in Table 2

TABLE 2

The aqueous formulations of examples 1 to 5 containing an inorganic acid or an organic acid group can exhibit stable solubilization properties. This is because calixarene is bonded to the pesticidal active ingredient to form an externally hydrophilic inclusion compound, whereby hydrophilicity is improved, and the pesticidal active ingredient is stably included in the calixarene. The host-guest inclusion ratio of the inclusion compound depends on the bonding constant of the pesticide and the calixarene. In contrast, in the comparative example, physical methods such as sonication, shaking, milling, etc. do not greatly affect the solubility of the drug.

These results show that the pesticidal formulation of the present invention has the advantage of being able to be solubilized. The dosage of organic reagent in the pesticide preparation is greatly reduced, and the toxicity in organisms and soil can be reduced.

The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various changes and modifications can be made without departing from the inventive concept, and these changes and modifications are all within the scope of the present invention.

Claims (9)

1. A pesticide formulation characterized by: the components comprise a pesticide active ingredient and calixarene, wherein the calixarene is represented by the following general formula:

in the formula: r₂Independently a hydrogen atom or a saturated or unsaturated, substituted or unsubstituted hydrocarbyl group;

R₁is an inorganic or organic acid group as a hydrophilic group;

n has a value of 4,5, 6 or 8;

the pesticide active ingredient has an aromatic ring forming a bond with the calixarene.

2. The pesticide formulation according to claim 1, characterized in that: the pesticide active ingredient is a compound or a composition with the effects of weeding or regulating the growth of plants or sterilizing or killing insects.

3. The pesticide formulation according to claim 2, characterized in that: the pesticide active ingredient is a compound with 1-4 aromatic rings.

4. A pesticide formulation according to claim 2 or 3, characterized in that: the pesticidal active ingredient is sparingly soluble in water or methanol.

5. The pesticide formulation according to claim 1, characterized in that: the R is₁Including substituted or unsubstituted carboxylic, sulfonic, phosphonic, amino acids, polyethylene glycol groups and their corresponding acid salts.

6. The pesticide formulation according to claim 5, characterized in that: the calixarene is one or a mixture of more than two of carboxyl azo calixarene or acid salt thereof, sulfo azo calixarene or acid salt thereof, phosphonic acid azo calixarene or acid salt thereof, quaternary ammonium salt azo calixarene, taurine azo calixarene or acid salt thereof, and polyethylene glycol azo calixarene or acid salt thereof.

7. The pesticide formulation according to claim 6, characterized in that: the calixarene is sulfoazo calixarene.

8. The pesticide formulation according to claim 1, characterized in that: the molar ratio of the calixarene to the pesticide active ingredient is 1-2.5.

9. The method for producing a pesticidal formulation according to any one of claims 1 to 8, characterized in that: mixing the pesticide active ingredient and the calixarene at room temperature or under heating.