CN117560993A - Liquid compositions comprising neonicotinoids - Google Patents
Liquid compositions comprising neonicotinoids Download PDFInfo
- Publication number
- CN117560993A CN117560993A CN202280023738.2A CN202280023738A CN117560993A CN 117560993 A CN117560993 A CN 117560993A CN 202280023738 A CN202280023738 A CN 202280023738A CN 117560993 A CN117560993 A CN 117560993A
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- Prior art keywords
- composition
- liquid
- surfactant
- amide solvent
- low polarity
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- 239000007788 liquid Substances 0.000 title claims abstract description 153
- 238000000034 method Methods 0.000 claims abstract description 34
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- 239000002904 solvent Substances 0.000 claims description 76
- 239000002917 insecticide Substances 0.000 claims description 71
- 239000012872 agrochemical composition Substances 0.000 claims description 61
- 150000001408 amides Chemical class 0.000 claims description 53
- 239000004094 surface-active agent Substances 0.000 claims description 48
- WCXDHFDTOYPNIE-RIYZIHGNSA-N (E)-acetamiprid Chemical compound N#C/N=C(\C)N(C)CC1=CC=C(Cl)N=C1 WCXDHFDTOYPNIE-RIYZIHGNSA-N 0.000 claims description 31
- 239000005875 Acetamiprid Substances 0.000 claims description 31
- 241000196324 Embryophyta Species 0.000 claims description 29
- -1 polyoxyethylene monooleate Polymers 0.000 claims description 28
- 239000000575 pesticide Substances 0.000 claims description 27
- 239000004495 emulsifiable concentrate Substances 0.000 claims description 20
- BNXZHVUCNYMNOS-UHFFFAOYSA-N 1-butylpyrrolidin-2-one Chemical compound CCCCN1CCCC1=O BNXZHVUCNYMNOS-UHFFFAOYSA-N 0.000 claims description 17
- 239000004530 micro-emulsion Substances 0.000 claims description 17
- 239000000463 material Substances 0.000 claims description 15
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 13
- 239000005907 Indoxacarb Substances 0.000 claims description 11
- VBCVPMMZEGZULK-NRFANRHFSA-N indoxacarb Chemical compound C([C@@]1(OC2)C(=O)OC)C3=CC(Cl)=CC=C3C1=NN2C(=O)N(C(=O)OC)C1=CC=C(OC(F)(F)F)C=C1 VBCVPMMZEGZULK-NRFANRHFSA-N 0.000 claims description 11
- GCKZANITAMOIAR-XWVCPFKXSA-N dsstox_cid_14566 Chemical compound [O-]C(=O)C1=CC=CC=C1.C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H]([NH2+]C)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 GCKZANITAMOIAR-XWVCPFKXSA-N 0.000 claims description 9
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- ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical compound CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 claims description 6
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- 125000000217 alkyl group Chemical group 0.000 claims description 6
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 claims description 6
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims description 6
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- ZXQYGBMAQZUVMI-RDDWSQKMSA-N (1S)-cis-(alphaR)-cyhalothrin Chemical compound CC1(C)[C@H](\C=C(/Cl)C(F)(F)F)[C@@H]1C(=O)O[C@@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-RDDWSQKMSA-N 0.000 claims description 5
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- ZOCSXAVNDGMNBV-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile Chemical compound NC1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ZOCSXAVNDGMNBV-UHFFFAOYSA-N 0.000 claims description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 4
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- ZXQYGBMAQZUVMI-UNOMPAQXSA-N cyhalothrin Chemical compound CC1(C)C(\C=C(/Cl)C(F)(F)F)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-UNOMPAQXSA-N 0.000 claims description 4
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- YWTYJOPNNQFBPC-UHFFFAOYSA-N imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 claims description 4
- PGOOBECODWQEAB-UHFFFAOYSA-N (E)-clothianidin Chemical compound [O-][N+](=O)\N=C(/NC)NCC1=CN=C(Cl)S1 PGOOBECODWQEAB-UHFFFAOYSA-N 0.000 claims description 3
- CFRPSFYHXJZSBI-DHZHZOJOSA-N (E)-nitenpyram Chemical compound [O-][N+](=O)/C=C(\NC)N(CC)CC1=CC=C(Cl)N=C1 CFRPSFYHXJZSBI-DHZHZOJOSA-N 0.000 claims description 3
- HOKKPVIRMVDYPB-UVTDQMKNSA-N (Z)-thiacloprid Chemical compound C1=NC(Cl)=CC=C1CN1C(=N/C#N)/SCC1 HOKKPVIRMVDYPB-UVTDQMKNSA-N 0.000 claims description 3
- AZSNMRSAGSSBNP-UHFFFAOYSA-N 22,23-dihydroavermectin B1a Natural products C1CC(C)C(C(C)CC)OC21OC(CC=C(C)C(OC1OC(C)C(OC3OC(C)C(O)C(OC)C3)C(OC)C1)C(C)C=CC=C1C3(C(C(=O)O4)C=C(C)C(O)C3OC1)O)CC4C2 AZSNMRSAGSSBNP-UHFFFAOYSA-N 0.000 claims description 3
- QMEQBOSUJUOXMX-UHFFFAOYSA-N 2h-oxadiazine Chemical compound N1OC=CC=N1 QMEQBOSUJUOXMX-UHFFFAOYSA-N 0.000 claims description 3
- OEDUIFSDODUDRK-UHFFFAOYSA-N 5-phenyl-1h-pyrazole Chemical compound N1N=CC=C1C1=CC=CC=C1 OEDUIFSDODUDRK-UHFFFAOYSA-N 0.000 claims description 3
- SPBDXSGPUHCETR-JFUDTMANSA-N 8883yp2r6d Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O[C@@H]([C@@H](C)CC4)C(C)C)O3)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1C[C@H](C)[C@@H]([C@@H](C)CC)O[C@@]21O[C@H](C\C=C(C)\[C@@H](O[C@@H]1O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C1)[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\1)O)C[C@H]4C2 SPBDXSGPUHCETR-JFUDTMANSA-N 0.000 claims description 3
- 239000005874 Bifenthrin Substances 0.000 claims description 3
- 239000005888 Clothianidin Substances 0.000 claims description 3
- FNELVJVBIYMIMC-UHFFFAOYSA-N Ethiprole Chemical compound N1=C(C#N)C(S(=O)CC)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl FNELVJVBIYMIMC-UHFFFAOYSA-N 0.000 claims description 3
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- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 3
- 239000005940 Thiacloprid Substances 0.000 claims description 3
- 239000005941 Thiamethoxam Substances 0.000 claims description 3
- YASYVMFAVPKPKE-UHFFFAOYSA-N acephate Chemical compound COP(=O)(SC)NC(C)=O YASYVMFAVPKPKE-UHFFFAOYSA-N 0.000 claims description 3
- RRZXIRBKKLTSOM-XPNPUAGNSA-N avermectin B1a Chemical compound C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 RRZXIRBKKLTSOM-XPNPUAGNSA-N 0.000 claims description 3
- OMFRMAHOUUJSGP-IRHGGOMRSA-N bifenthrin Chemical compound C1=CC=C(C=2C=CC=CC=2)C(C)=C1COC(=O)[C@@H]1[C@H](\C=C(/Cl)C(F)(F)F)C1(C)C OMFRMAHOUUJSGP-IRHGGOMRSA-N 0.000 claims description 3
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- KRTSDMXIXPKRQR-AATRIKPKSA-N monocrotophos Chemical compound CNC(=O)\C=C(/C)OP(=O)(OC)OC KRTSDMXIXPKRQR-AATRIKPKSA-N 0.000 claims description 3
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- 239000002728 pyrethroid Substances 0.000 claims description 3
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical group O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 3
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 claims description 3
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- XUNYDVLIZWUPAW-UHFFFAOYSA-N (4-chlorophenyl) n-(4-methylphenyl)sulfonylcarbamate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)OC1=CC=C(Cl)C=C1 XUNYDVLIZWUPAW-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/86—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Detergent Compositions (AREA)
- Fats And Perfumes (AREA)
Abstract
Disclosed herein are stable liquid agrochemical compositions. Also disclosed are methods of preparing the liquid agrochemical compositions, the use of the liquid compositions for controlling pests, and methods of controlling pests using the liquid agrochemical compositions.
Description
Technical Field
The present disclosure relates to liquid agrochemical compositions comprising a neonicotinoid insecticide, methods of making the liquid agrochemical compositions, the use of the liquid compositions for controlling pests, and methods of controlling pests using the liquid agrochemical compositions.
Background
The neonicotinoid pesticide has a unique action mechanism. Unlike pesticides, which evaporate or disperse soon after application, neonicotinoid insecticides are systemic pesticides. They are less toxic than organic phosphates and carbamates, which provide similar broad spectrum control over many crop-damaging insects. Neonicotinoid insecticides paralyze insects by blocking pathways in the insect central nervous system that transmit nerve impulses. Neonicotinoid insecticides are used to control a wide variety of insects. Typical neonicotinoid insecticides are imidacloprid, acetamiprid, clothianidin, dinotefuran, nitenpyram, thiacloprid and thiamethoxam.
Acetamiprid is a neonicotinoid pesticide used for foliar spray and seed treatment. Acetamiprid is slightly soluble in water and therefore its liquid formulations often exhibit stability problems. Suspension Concentrate (SC), emulsifiable Concentrate (EC) and Microemulsion (ME) formulations of acetamiprid are known to have stability problems. Emulsifiable concentrates are stable liquid, homogeneous liquid formulations comprising an insecticidal active ingredient, a solvent and an emulsifier. When diluted with water, they form an emulsion upon dilution in water. The stable suspension contains the active ingredient in a continuous phase with water and is intended to be diluted with water before use. The microemulsion comprises the active ingredient, oil and water and may be applied directly or after dilution in water.
Suspension Concentrate (SC) formulations comprising acetamiprid are known to be prone to rapid formation of crystals, gelation, caking and sedimentation. Emulsifiable Concentrate (EC) formulations comprising acetamiprid are known to crystallize and cause nozzle clogging upon dilution with water. Microemulsions (ME) containing acetamiprid also face stability problems and require large amounts of surfactants to achieve thermodynamic stability. These problems are further exacerbated when formulators attempt to achieve high loadings of active ingredient in acetamiprid liquid formulations alone or in combination with other active ingredients that can withstand extreme temperatures, especially low temperatures.
There is a need to develop stable agrochemical compositions comprising neonicotinoid insecticides which do not present stability problems and are stable at low temperatures.
The purpose of the disclosure is as follows:
it is an object of the present disclosure to provide stable liquid agrochemical compositions comprising a neonicotinoid insecticide.
It is another object of the present disclosure to provide stable liquid agrochemical compositions comprising high load neonicotinoid insecticides alone or in combination with additional pesticides.
It is a further object of the present disclosure to provide stable liquid agrochemical compositions capable of withstanding low temperatures comprising high loadings of neonicotinoid insecticides alone or in combination with additional pesticides.
It is a further object of the present disclosure to provide a method of preparing a liquid agrochemical composition comprising a high load neonicotinoid insecticide alone or in combination with an additional pesticide.
Disclosure of Invention
In one aspect, the present disclosure provides a liquid agrochemical composition comprising:
(a) At least one neonicotinoid insecticide;
(b) At least one low polarity amide solvent; and
(c) At least one surfactant having an HLB value of from about 10 to about 18.
In another aspect, the present disclosure provides a liquid agrochemical composition comprising:
(a) At least one neonicotinoid insecticide;
(b) At least one low polarity amide solvent;
(c) At least one surfactant having an HLB value of from 10 to about 18; and
(d) An additional insecticide.
In yet another aspect, the present disclosure provides a method of preparing a liquid agrochemical composition, wherein the method comprises: at least one neonicotinoid insecticide is combined with at least one low polarity amide solvent and at least one surfactant having an HLB value of from about 10 to about 18.
In another aspect, the present disclosure provides a use of a liquid agrochemical composition for controlling pests, the liquid agrochemical composition comprising:
(a) At least one neonicotinoid insecticide;
(b) At least one low polarity amide solvent; and
(c) At least one surfactant having an HLB value of from about 10 to about 18.
In another aspect, the present disclosure provides the use of a liquid agrochemical composition to control pests by application to plants or to the locus where plants are growing or are to be planted or to plant propagation material or locus where plants are suitable.
In another aspect, the present disclosure provides a method of controlling pests, the method comprising applying to a plant or to a locus where the plant is growing or is to be grown or to plant propagation material or locus where it is suitable, a liquid agrochemical composition comprising:
(a) At least one neonicotinoid insecticide;
(b) At least one low polarity amide solvent; and
(c) At least one surfactant having an HLB value of from about 10 to about 18.
In another aspect, the present disclosure provides a kit comprising a plurality of components, each of which may comprise at least one or more ingredients of a liquid composition according to the present disclosure.
Other features and advantages of the present disclosure will become apparent from the following detailed description, which illustrates by way of example the most preferred features of the present disclosure, which should not be construed to limit the scope of the disclosure described herein.
Detailed Description
For purposes of the following detailed description, it is to be understood that the present disclosure may assume various alternative variations, except where expressly specified to the contrary. Furthermore, all numbers expressing, for example, quantities of materials/ingredients used in the specification are to be understood as being modified in all instances by the term "about" except in any operating example, or unless otherwise indicated.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure belongs. If ambiguous, the text (including definitions) controls.
Recitation of ranges of values herein are merely intended to serve as a shorthand method of referring individually to each separate value falling within the range, unless otherwise indicated herein, and each separate value is incorporated into the specification as if it were individually recited herein. All endpoints of the ranges are inclusive of the range and independently combinable. As used herein, unless the context clearly indicates otherwise, all numbers or ranges of numbers include integers within such ranges as well as values or fractions of integers within the range. Thus, for example, reference to a range of 90% -100% includes 91%, 92%, 93%, 94%, 95%, 97%, etc., as well as 91.1%, 91.2%, 91.3%, 91.4%, 91.5%, etc., 92.1%, 92.2%, 92.3%, 92.4%, 92.5%, etc., and the like. All methods described herein can be performed in the proper order unless otherwise indicated herein or otherwise clearly contradicted by context.
As used herein, "a," "an," "the," and "at least one" do not denote a limitation of quantity and are intended to cover both the singular and the plural, unless the context clearly indicates otherwise. For example, "an element" has the same meaning as "at least one element" unless the context clearly indicates otherwise. As used herein, the terms "first," "second," and the like are not intended to denote any particular order, but rather merely for convenience to denote multiple layers, for example. As used herein, the terms "comprising," "including," "having," "containing," "involving," and the like are to be construed as open-ended, i.e., to mean including but not limited to, unless otherwise noted. As used herein, "about" or "approximately" includes the specified values and means within an acceptable deviation of the specified values, which is determined by one of ordinary skill in the art in view of the measurement in question and the specified amount of error associated with the measurement (i.e., limitations of the measurement system). For example, "about" may mean within one or more standard deviations, or within a range of ±10% or ±5% of the specified value. The use of any and all examples, or exemplary language (e.g., "such as") provided herein, is intended merely to better illuminate the invention and does not pose a limitation on the scope of the invention unless otherwise claimed. No language in the specification should be construed as indicating any non-claimed element as essential to the practice of the invention as used herein.
In any aspect or embodiment described below, the phrase "comprising" may be replaced by the phrase "consisting of … …" or "consisting essentially of … …" or "consisting essentially of … …". In these aspects or embodiments, the described compositions comprise or consist of or consist essentially of the specific components recited therein, excluding other ingredients or excipients specifically recited therein.
While the disclosure has been described with reference to exemplary embodiments, it will be understood by those skilled in the art that various changes may be made and equivalents may be substituted for elements thereof without departing from the scope of the disclosure. In addition, many modifications may be made to adapt a particular situation or material to the teachings of the invention without departing from the essential scope thereof. Therefore, it is intended that the invention not be limited to the particular embodiment disclosed as the best mode contemplated for carrying out this invention, but that the invention will include all embodiments falling within the scope of the appended claims. The invention encompasses any combination of the above-described elements in all possible variations thereof unless otherwise indicated herein or otherwise clearly contradicted by context.
"alkyl" means a straight or branched chain saturated aliphatic hydrocarbon having the specified number of carbon atoms, specifically 1 to 12 carbon atoms, more specifically 1 to 6 carbon atoms. Alkyl groups include, for example, groups having 1 to 50 carbon atoms (C 1 To C 50 Alkyl).
"alkylene" means a straight or branched, saturated divalent aliphatic hydrocarbon group (e.g., methylene (-CH) 2 (-) or propylene (- (CH) 2 )3-))。
As used throughout this disclosure, neonicotinoid insecticides or other active ingredients include their salts, esters, ethers, isomers, and polymorphs including solvates and hydrates. Salts include those which retain the biological effectiveness and properties of the active ingredient and are not biologically or otherwise undesirable, and include derivatives of the disclosed compounds wherein the parent compound is modified by preparing inorganic and organic, non-toxic acid or base addition salts thereof. Salts can be synthesized from the parent compound by conventional chemical methods. "solvate" means a pesticide or agriculturally acceptable salt thereof in which a molecule of a suitable solvent is incorporated into the lattice. Suitable solvents are physiologically tolerable at the doses administered. Examples of suitable solvents are ethanol, water, and the like. When water is the solvent, the molecule is referred to as a "hydrate". The formation of solvates will vary depending on the compound and the solvate. In general, solvates are formed by dissolving the compound in an appropriate solvent and isolating the solvate by cooling or using an antisolvent. The solvates are typically dried or azeotroped at ambient conditions. In one aspect, the solvate is a hydrate.
The term "plant" refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, leaves, and fruits. The term plant includes transgenic plants and non-transgenic plants.
The term "locus" as used herein refers to the vicinity, region or site of plant growth, plant propagation material in which plants are sown (e.g., placed in soil), and/or plant propagation material in which plants are to be sown.
The term "plant propagation material" refers to reproductive parts of plants, such as seeds, nutritional materials, such as cuttings or tubers, roots, fruits, tubers, bulbs, rhizomes, and other parts of plants, germinated plants and/or seedlings, which are transplanted after germination or after emergence from soil. These seedlings may be protected by a complete or partial soaking process/system prior to transplantation.
As used herein, an "effective amount" is an amount of an active ingredient (such as a combination disclosed) that has an adverse effect on the insect and/or that prevents diseases caused by the insect in the plant. Adverse effects may include killing the insect (insecticidal), preventing insect growth, blocking biosynthetic pathways, or combinations thereof.
As used herein, "agriculturally acceptable salt" means a salt that has been accepted for agricultural or horticultural use.
Low temperature stability is a critical requirement for liquid agrochemical formulations (such as EC and ME) because they often need to be used in low temperature areas or exposed to low temperatures. In cold climates, precipitation of active substances at low temperatures or freezing of such liquid formulations can lead to practical difficulties in handling the product and to low biological efficacy. Stability, particularly low temperature stability, is of great concern when liquid formulations are exposed to low temperatures, i.e., from about 20 ℃ to about-10 ℃.
Surprisingly, the inventors of the present disclosure have found that liquid agrochemical compositions of stable neonicotinoid insecticides, alone or in combination with additional pesticides, can be obtained by incorporating a low polarity amide solvent and a surfactant having an HLB value of from about 10 to about 18. The inventors have also found that by combining a low polarity amide solvent with a surfactant having an HLB value of 10-18, a high loading of a neonicotinoid insecticide in a liquid agrochemical composition is possible. The highly loaded compositions thus obtained were found to be able to withstand extremely low temperatures and to remain fairly stable throughout storage and during application after dilution with water.
Accordingly, one embodiment of the present disclosure provides a liquid agrochemical composition comprising:
(a) At least one of the class of the neonicotinoid insecticides,
(b) At least one low polarity amide solvent, and
(c) At least one surfactant having an HLB value of from 10 to 18.
According to another embodiment, the liquid agrochemical composition is stable at low temperatures.
In another embodiment, the term "low polarity amide solvent" is meant to include N-C 2-8 Alkyl pyrrolidone group and polarity value of 0.350.
In another embodiment, the term "low polarity amide solvent" is meant to include N-C 2-8 Alkyl pyrrolidone and polarity values lower than the rickettsia (Reichardt) polarity scale (E T N ) 0.340 solvent.
As used throughout this specification, the term "low temperature" refers to a temperature range of 20 ℃ to about-10 ℃.
According to one embodiment, the liquid agrochemical composition is stable at temperatures below 20 ℃.
According to another embodiment, the liquid agrochemical composition is stable at temperatures below 10 ℃.
According to yet another embodiment, the liquid agrochemical composition is stable at temperatures below 5 ℃.
According to yet another embodiment, the liquid agrochemical composition is stable at temperatures below 0 ℃.
According to yet another embodiment, the liquid agrochemical composition is stable at temperatures below-5 ℃.
According to one embodiment, the liquid agrochemical composition comprises at least one neonicotinoid insecticide.
According to another embodiment, the neonicotinoid insecticide is selected from the group consisting of: acetamiprid, clothianidin, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, and combinations thereof.
According to yet another embodiment, the neonicotinoid insecticide comprises imidacloprid.
According to a preferred embodiment, the neonicotinoid insecticide comprises acetamiprid.
According to one embodiment, the liquid agrochemical composition comprises from about 0.1% w/w to about 90% w/w of the neonicotinoid insecticide, based on the total weight of the liquid composition.
According to another embodiment, the liquid agrochemical composition comprises from about 10% w/w to about 80% w/w of the neonicotinoid insecticide, based on the total weight of the liquid composition.
In a preferred embodiment, the liquid agrochemical composition comprises from about 20% w/w to about 70% w/w of the neonicotinoid insecticide, based on the total weight of the liquid composition.
According to one embodiment, the liquid agrochemical composition comprises at least one low polarity amide solvent.
According to another embodiment, the low polarity amide solvent comprises N-C 2-8 Alkyl pyrrolidone groups.
According to another embodiment, the present disclosure provides a liquid composition comprising:
(a) At least one of the class of the neonicotinoid insecticides,
(b) At least one low polarity amide solvent, wherein the low polarity amide solvent comprises N-C 2-8 Alkyl pyrrolidone, and
(c) At least one surfactant having an HLB value of from 10 to about 18.
According to yet another embodiment, the low polarity amide solvent is selected from the group consisting of: n-butylpyrrolidone (NBP), n-octylpyrrolidone, and n-ethylpyrrolidone (NEP).
According to yet another embodiment, the low polarity amide solvent is selected from the group consisting of: n-butylpyrrolidone (NBP) and n-ethylpyrrolidone (NEP).
According to yet another embodiment of the present disclosure, the low polarity amide solvent is n-butyl pyrrolidone (NBP).
According to one embodiment, the liquid agrochemical composition comprises from about 1% w/w to about 90% w/w of the low polarity amide solvent, based on the total weight of the liquid composition.
According to one embodiment, the liquid agrochemical composition comprises from about 10% w/w to about 80% w/w of the low polarity amide solvent, based on the total weight of the liquid composition.
In a preferred embodiment, the liquid agrochemical composition comprises from about 20% w/w to about 75% w/w of the low polarity amide solvent, based on the total weight of the liquid composition.
According to one embodiment, the liquid agrochemical composition comprises at least one surfactant having an HLB ranging from about 10 to about 18.
According to another embodiment, the liquid agrochemical composition comprises at least one surfactant having an HLB ranging from about 10 to about 18 selected from the group consisting of: sorbitan derivatives and ethylene oxide-propylene oxide (EO/PO) block copolymers.
According to one embodiment of the present disclosure, the sorbitan derivative is selected from the group consisting of sorbitan esters and ethoxylated sorbitan esters having an HLB ranging from about 10 to about 18.
According to another embodiment, the sorbitan derivative is selected from the group consisting of: polyoxyethylene monooleate, polyoxyethylene monostearate, polyoxyethylene monolaurate, polyoxyethylene sorbitan monopalmitate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan tristearate, polyoxyethylene sorbitan monooleate and polyoxyethylene sorbitan trioleate.
According to yet another embodiment, the ethoxylated sorbitan ester is polyoxyethylene sorbitan monooleate.
According to yet another embodiment, the EO/PO block copolymer having an HLB ranging from 10 to 18 is selected from the group consisting of: block copolymers of ethylene oxide, propylene oxide and propylene glycol, ethylene oxide, methyl-, ethylene oxide polymers and butyl EO/PO block polymers.
According to one embodiment, the liquid agrochemical composition comprises from about 0.01% w/w to about 50% w/w of a surfactant having an HLB in the range of from about 10 to about 18, based on the total weight of the liquid composition.
According to another embodiment, the liquid agrochemical composition comprises from about 0.1% w/w to about 40% w/w of a surfactant having an HLB in the range of from about 10 to about 18, based on the total weight of the liquid composition.
According to yet another embodiment, the liquid agrochemical composition comprises from about 0.5% w/w to about 30% w/w of a surfactant having an HLB in the range of 10-18, based on the total weight of the liquid composition.
According to one embodiment, the liquid agrochemical composition may be formulated as emulsifiable concentrates, soluble liquids, microemulsions, suspension concentrates, suspoemulsions and oil dispersions.
According to one embodiment, a liquid agrochemical composition comprises:
(a) At least one of the class of the neonicotinoid insecticides,
(b) At least one of the pesticides is used in combination with a pesticide,
(c) At least one low polarity amide solvent, and
(d) At least one surfactant having an HLB value of from about 10 to about 18.
According to one embodiment, the liquid agrochemical composition comprises a further pesticide.
According to one embodiment, the liquid agrochemical composition comprises one or more pesticides selected from the group consisting of oxadiazine pesticides, avermectin pesticides, thiophosphamide pesticides, phenylpyrazole pesticides, benzoylurea pesticides, pyrethroid pesticides, salts, esters, optically active isomers and combinations thereof.
According to one embodiment, the liquid agrochemical composition comprises one or more pesticides selected from the group consisting of: oxadiazine insecticides such as indoxacarb (indoxacarb); avermectins insecticides such as avermectin (abamectin), doramectin (doramectin), emamectin (emamectin), eprinomectin (epidomycin), ivermectin (ivermectin) and selamectin (selamectin); thiophosphamide insecticides such as acephate (acephate), methamidophos (methamidophos), monocrotophos (monocrotophos); phenylpyrazole insecticides such as fluofos (flupyrazofos), pyraclostrobin (pyraclofos), pyrrocarb (pyrolan), ethiprole (ethiprole), fipronil (fipronil), and fipronil (fifipronil); pyridylpyrazole insecticides such as chlorantraniliprole, cyantraniliprole, cyclobrimonide, tetrachlorethamide, tetrazolamide; benzoyl urea-type insecticides such as lufenuron (lufenuron), novaluron (novaluron), diflubenzuron (dibenzuron), chlorfluazuron (chlorfluazuron); pyrethroid insecticides such as bifenthrin (bifenthrin), cyhalothrin (cyfluthrin), lambda-cyhalothrin (beta-cyfluthrin), cyhalothrin (cyhalothrin), lambda-cyhalothrin (gamma-cyhalothrin), lambda-cyhalothrin (lambda-cyhalothrin), cypermethrin (cypermethrin), cis-cyhalothrin (alpha-cypermethrin), beta-cypermethrin (beta-cypermethrin), beta-cypermethrin (theta-cypermethrin), beta-cypermethrin (cyphenothrin), deltamethrin (deltamethrin), dimefluthrin (dimefluthrin), fenvalerate (fenvalerate) and transfluthrin (transfluthrin).
According to another embodiment, the liquid agrochemical composition comprises from about 1% w/w to about 90% w/w of a neonicotinoid insecticide, from 1% w/w to about 40% w/w of an additional insecticide, from about 20% w/w to about 90% w/w of a low polarity amide solvent, and from about 0.1% w/w to about 10% w/w of a surfactant having an HLB value in the range of from 10 to about 18.
According to yet another embodiment, the liquid agrochemical composition comprises about 1% to 90% w/w acetamiprid, 1% to 40% w/w emamectin benzoate, about 20% to 90% w/w of a low polarity amide solvent comprising n-butyl pyrrolidone, and about 0.1% to 10% w/w of a surfactant having an HLB value in the range of 10-18.
According to yet another embodiment, the liquid agrochemical composition comprises about 1% to 90% w/w acetamiprid, 1% to 40% w/w indoxacarb, about 20% to 90% w/w of a low polarity amide solvent comprising n-butyl pyrrolidone, and about 0.1% to 10% w/w of a surfactant having an HLB value in the range of 10 to about 18.
According to one embodiment, the liquid agrochemical composition may further comprise one or more additional solvents.
According to another embodiment, the additional solvent is selected from the group consisting of: a non-polar water-immiscible solvent or a polar aprotic water-miscible organic solvent.
According to yet another embodiment, the additional solvent in the liquid composition is selected from polar and non-polar water-immiscible solvents, substituted or unsubstituted aromatic or aliphatic hydrocarbons and alkyl esters of vegetable oils or mixtures thereof.
According to one embodiment, the liquid composition comprises a further polar solvent selected from the group consisting of: cyclohexanone; dibasic esters such as, but not limited to, dimethyl 2-methylglutarate, and dibasic ester mixtures consisting of dimethyl glutarate, dimethyl succinate and dimethyl adipate; glycol ethers and polyalkylene diglycol ethers such as, but not limited to, dipropylene glycol methyl ether; alkylene carbonates such as, but not limited to, propylene carbonate; 5- (dimethylamino) -2-methyl-5-oxopentanoic acid methyl ester; ketones such as, but not limited to, cyclopentanone and cyclohexanone; the water-miscible polar aprotic solvents include, for example, alkyl lactate, isopropyl lactate, alkyl carbonate, polyethylene glycol alkyl ether, monopropylene glycol, polypropylene glycol and polypropylene glycol alkyl ether, or mixtures thereof.
According to one embodiment, the additional solvent in the liquid composition is a fatty acid ester solvent, such as C prepared from vegetable oil 6- C 14 Fatty acid esters.
According to one embodiment, the additional solvent in the liquid composition is selected from one or more of the following: aromatic hydrocarbons derived from benzene, such as toluene, xylene, mesitylene, diisopropylbenzene and its higher homologs, indanes and naphthalene derivatives, such as 1-methylnaphthalene, 2-methylnaphthalene; c (C) 5 -C 12 Aliphatic hydrocarbons (linear, branched or cyclic) such as pentane, hexane, cyclohexane, octane, 2-ethyl hexane, decane; c (C) 4 -C 10 Fatty alcohols (straight or branched) such as butan-1-ol, hexanol, 2-ethylbutanol, heptanol, octanol, 2-octanol, and 2-ethylhexanol; and aromatic alcohols such as benzyl alcohol.
According to one embodiment, the solvent in the liquid composition is selected from mineral oils.
According to one embodiment, the solvent in the liquid composition is selected from water-miscible polar aprotic solvents including, for example, alkyl lactate, isopropyl lactate, alkyl carbonate, polyethylene glycol alkyl ether, monopropylene glycol, polypropylene glycol and polypropylene glycol alkyl ether, or mixtures thereof.
According to one embodiment, the liquid composition comprises about 1% w/w to about 99% w/w of the additional solvent based on the total weight of the liquid composition.
According to another embodiment, the liquid composition comprises about 10% w/w to about 90% w/w of the additional solvent based on the total weight of the liquid composition.
According to another embodiment, the additional solvent comprises water.
According to a preferred embodiment of the present disclosure, the liquid composition comprises from about 30% w/w to about 80% w/w solvent based on the total weight of the liquid composition.
According to one embodiment, the liquid composition may comprise one or more adjuvants selected from the group consisting of: surfactants (emulsifiers), crop oils, fertilizers, dispersants, compatibilizers, defoamers, biocides, antioxidants, flavoring agents and spray colorants (dyes).
According to one embodiment, the liquid composition comprises an antioxidant selected from the group consisting of: butyl Hydroxy Anisole (BHA), butyl Hydroxy Toluene (BHT), tertiary Butyl Hydroquinone (TBHQ) and Propyl Gallate (PG) and mixtures thereof.
According to another embodiment, the liquid composition comprises an antifoaming agent selected from the group consisting of: silicone-based compounds, alcohols, glycol ethers, mineral spirits, acetylene glycol, polysiloxanes, organosiloxanes, siloxane glycols, reaction products of silica and organosiloxane polymers, polydimethylsiloxanes or polyalkylene glycols alone or in combination.
According to one embodiment, the liquid composition optionally comprises from about 0.1% w/w to about 40% w/w of one or more adjuvants, based on the total weight of the emulsifiable concentrate composition.
According to one embodiment, the liquid composition optionally comprises from about 0.5% w/w to about 30% w/w of one or more adjuvants, based on the total weight of the emulsifiable concentrate composition.
According to one embodiment, the liquid composition comprises from about 0.1% w/w to about 90% w/w of the neonicotinoid insecticide, from 0.01% w/w to about 90% w/w of the low polarity amide solvent, from about 0.01% w/w to about 50% w/w of the surfactant having an HLB value of from about 10 to about 18, based on the total weight of the liquid composition.
According to another embodiment, the liquid composition comprises from about 1% w/w to about 40% w/w of the neonicotinoid insecticide, from 10% w/w to about 80% w/w of the low polarity amide solvent, from about 0.01% w/w to about 30% w/w of the surfactant having an HLB value of from about 10 to about 18, based on the total weight of the liquid composition.
According to another embodiment, the liquid composition comprises from about 1% w/w to about 40% w/w of the neonicotinoid insecticide, from 20% w/w to about 75% w/w of the low polarity amide solvent, from about 0.01% w/w to about 20% w/w of the surfactant having an HLB value of from about 10 to about 18, based on the total weight of the liquid composition.
According to another embodiment of the present invention, the liquid composition comprises from about 0.1% w/w to about 90% w/w acetamiprid, from 0.01% w/w to about 90% w/w of a low polarity amide solvent comprising n-butyl pyrrolidone, from about 0.01% w/w to about 50% w/w of a surfactant comprising polyoxyethylene sorbitan monooleate, having an HLB value in the range of from about 10 to about 18, based on the total weight of the liquid composition.
The liquid agrochemical composition described in any of the embodiments of the present specification may be a Microemulsion (ME) unless the context requires otherwise.
The liquid agrochemical composition described in any of the embodiments of the present specification may be a Soluble Liquid (SL) unless the context requires otherwise.
The liquid agrochemical composition described in any of the embodiments of the present specification may be an Emulsifiable Concentrate (EC) unless the context requires otherwise.
In one embodiment, the present disclosure provides a method of preparing a liquid agrochemical composition, wherein the method comprises: at least one neonicotinoid insecticide is combined with at least one low polarity amide solvent and at least one surfactant having an HLB value of from about 10 to about 18.
In one embodiment, the present disclosure provides a method of preparing a soluble liquid agrochemical composition, wherein the method comprises:
combining at least one neonicotinoid insecticide with at least one low polarity amide solvent to obtain a mixture;
combining water and a surfactant having an HLB value ranging from about 10 to about 18 with the mixture; and
a mixture of at least one neonicotinoid insecticide, at least one low polarity amide solvent, water and a surfactant is homogenized to obtain a soluble liquid agrochemical composition.
In one embodiment, the present disclosure provides a method of preparing an emulsifiable concentrate agrochemical composition, wherein the method comprises:
combining at least one neonicotinoid insecticide with at least one low polarity amide solvent to obtain a mixture;
combining water and a surfactant having an HLB value ranging from about 10 to about 18 with the mixture; and
a mixture of at least one neonicotinoid insecticide, at least one low polarity amide solvent, water and a surfactant is homogenized to obtain an emulsifiable concentrate agrochemical composition.
In one embodiment, the present disclosure provides a method of preparing a microemulsion agrochemical composition, wherein the method comprises:
Combining water and at least one neonicotinoid insecticide to obtain a mixture;
combining a surfactant having an HLB value within the range of from about 10 to about 18 with the mixture; and homogenizing the mixture of at least one neonicotinoid insecticide, at least one low polarity amide solvent, water and surfactant to obtain a microemulsion agrochemical composition.
In another embodiment, the method of combining at least one neonicotinoid insecticide with at least one low polarity amide solvent to obtain a mixture involves agitation.
In yet another embodiment, the method of combining at least one neonicotinoid insecticide with water to obtain a mixture involves stirring.
In yet another embodiment, the method of combining at least one neonicotinoid insecticide, water, and at least one low polarity amide solvent to obtain a mixture involves stirring.
In yet another embodiment, wherein the liquid agrochemical composition comprises at least one neonicotinoid insecticide and an additional pesticide, the method comprises combining the at least one neonicotinoid insecticide and the additional pesticide with at least one low polarity amide solvent. According to one embodiment, the homogenizing comprises particle size reduction.
According to another embodiment, the particle size reduction is achieved by applying shear to a mixture of the active ingredient, the low polarity amide solvent and the surfactant having an HLB in the range of 10-18 and optionally other adjuvants. Suitable devices for applying shear include any high shear device, such as high shear mixers (such as Ultra-Turrax devices), as well as dissolvers, static mixers (e.g., systems with mixing nozzles), bead mills, vibratory mills, stirred bead mills, colloid mills, cone mills, circulating mills (stirred ball mills with pin milling systems), disc mills, annular chamber mills, double cone mills, sprocket dispersers or homogenizers, and other homogenizers.
According to one embodiment, the liquid composition is intended to be diluted with water (or a water-based liquid) to form a corresponding end use agrochemical formulation, typically a spray formulation.
According to one embodiment, the liquid composition has a pH in the range of 5-7.
According to one embodiment, the liquid composition does not change by more than 20% in pH between 24 hours and 28 days at 54 ℃.
According to one embodiment of the invention, the liquid composition does not change by more than 10% in pH between 24 hours and 28 days at 54 ℃.
According to one embodiment of the invention, the liquid composition does not change by more than 5% in pH between 24 hours and 28 days at 54 ℃.
According to one embodiment, the liquid composition provides a formulation that allows the active compound to be absorbed by the plant/target organism.
According to one embodiment, the liquid composition is used as a source of active agrochemical ingredients and is diluted to form an end use formulation, typically a spray formulation.
In one embodiment, dilution with 1 to 10,000 times, particularly 10 to 1,000 times the total weight of the composition, of water may be performed to form a spray formulation.
In one embodiment, the agrochemical active concentration in the diluted composition may be in the range of about 0.001wt.% to about 1wt.% of the total spray formulation.
In one embodiment, the spray formulation may be prepared by simple dilution of a liquid agrochemical composition.
In another embodiment, spray formulations may be prepared by combining the individual components used to prepare the liquid agrochemical composition with water.
Typically, such end use mixing is performed in a tank of sprayed formulation, or alternatively in a storage tank for filling a spray tank. Such mixtures and blends are commonly referred to as tank mixes and tank blends.
According to another embodiment, there is provided a method of controlling pests, the method comprising applying to a plant or to a locus where the plant is growing or is to be grown or to plant propagation material or a locus where it is suitable, a liquid composition comprising:
(a) At least one neonicotinoid insecticide;
(b) At least one low polarity amide solvent; and
(c) At least one surfactant having an HLB value of from 10 to 18.
According to another embodiment, a method of controlling pests includes applying a liquid composition comprising acetamiprid.
According to another embodiment of the present invention, a method of controlling pests comprises applying a liquid composition comprising acetamiprid and an additional pesticide.
Examples of crops that can use the compositions of the present invention include, but are not limited to, corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, buckwheat, beet, rapeseed, sunflower, sugarcane, tobacco, and the like; vegetables: eggplant vegetables such as eggplant, tomato, sweet pepper, potato, etc., melon vegetables such as cucumber, pumpkin, zucchini, watermelon, melon, pumpkin, etc., cruciferous vegetables such as radish, white radish, horseradish, kohlrabi, cabbage, mustard, broccoli, cauliflower, etc., compositic vegetables such as burdock, crown wormwood, artichoke, lettuce, etc., liliaceous vegetables such as green onion, garlic, and asparagus, sub-micaceous vegetables such as carrot, parsley, celery, parsnip, etc., chenopodiaceae vegetables such as spinach, lettuce, etc., labiatae vegetables such as bust, peppermint, basil, etc., strawberry, sweet potato, yam, taro, etc., flowers, foliage plants, turf grass, fruit: pome fruits such as apples, pears, quince, etc., stone fruits such as peaches, plums, nectarines, plums, cherries, apricots, plums, etc., citrus fruits such as oranges, lemons, fogs, grapefruits, etc., nuts such as chestnuts, walnuts, hazelnuts, almonds, pistachios, cashews, hawaii nuts, etc., berries such as blueberries, cranberries, blackberries, raspberries, etc., grapes, persimmons, olives, plums, bananas, coffee, date palm, coconuts, etc., trees other than fruit trees; tea tree, mulberry, flowering plant, tree such as chinese wax, birch, dogwood, eucalyptus, ginkgo, clove, maple, oak, poplar, koku, cercis, sweetgum, syringa, zelkova, japanese arborvitae, fir, hemlock, pine, spruce, and taxus northeast, etc.
In one embodiment, pests to be controlled by the compositions of the present invention include, but are not limited to, mealybugs (Planococcus citri) and Panonychus citri (panoneichus citri).
According to one embodiment, a kit comprising a liquid composition contains a plurality of components, each of which may comprise at least one or more of the ingredients of the liquid composition.
The compositions described throughout this disclosure have insecticidal activity and are stable. It has been found that the combination of a low polarity amide solvent and a surfactant having an HLB in the range of about 10 to about 18 provides excellent stability over time and at various temperatures, even when the liquid composition is subjected to shear forces (e.g., upon mixing). Moreover, the liquid compositions obtained have excellent suspension, dispersibility, very low or no sedimentation and little particle degradation.
All features described in this disclosure may be combined with any other aspect or any embodiment in any combination.
These and other advantages of the present disclosure may become more apparent from the examples described below. These examples are provided only as illustrations of the present disclosure and are not intended to be construed as limiting the present disclosure.
All of the listed tests and physical properties have been determined at atmospheric pressure and room temperature (i.e., 25 ℃) unless otherwise indicated herein or unless otherwise indicated in the test methods and procedures referenced.
Examples
Example 1: acetamiprid 200g/L Soluble Liquid (SL) (working example)
200g/L acetamiprid soluble liquid compositions were prepared using the materials in Table 1.
TABLE 1
654.5g of n-butylpyrrolidone were charged into a mixing vessel, followed by 200g of acetamiprid and mixing until dissolved. Water was added to the same mixing vessel to obtain a mixture. 43g of polyoxyethylene sorbitan monooleate and 2g of a silicone defoamer were added to the mixture and homogenized for about 5 minutes to give a soluble liquid formulation.
Stability data
The composition of example-1 was subjected to physicochemical studies under different test conditions such as ambient temperature (room temperature) test and at low temperature. The composition of example-1 was subjected to a low temperature test after 7 days at 0 ℃, the sample was kept in an oven for 2 weeks at 54 ℃ and for 8 weeks at 40 ℃ to accelerate thermal stability (AHS) for oven stability. Cryogenic studies were performed according to CIPAC method No. 39.3, wherein the composition was maintained at 0 ℃ for 1h, and then the volume of any isolated solid or oily material was recorded. Storage was continued for 7 days at 0 ℃, any solid material was settled by centrifugation and its volume was recorded. The composition of example-1 remained as a clear pale yellow liquid under all four stability conditions. The density of the composition is maintained at about 1 and the degradation of activity is maintained within acceptable limits. The permanent foam in the composition remains within an acceptable range. And the pH of the composition was found to be around 7 under all conditions.
TABLE 2
Example 2: acetamiprid 120g/l + emamectin benzoate 15g/l ME (working example)
Acetamiprid 120g/l + emamectin benzoate 15g/l ME was prepared using the materials in table 3.
TABLE 3 Table 3
12.5g of propylene glycol was charged into a mixing vessel, and then 38.5g of butan-1-ol was added under shaking to obtain a mixture. 7g of butyl hydroxy anisole and water were added to the mixture and mixed for about 5 minutes. To the same mixture, 16g of emamectin benzoate and then 764.8g of n-butylpyrrolidone were added with continuous mixing. An additional 122.4g acetamiprid was added and mixed for about 30 minutes until completely dissolved. 8g of polyoxyethylene (20) sorbitan monooleate and 0.3g of an organosilicon defoamer were added and mixed to obtain a microemulsion.
Stability data
The composition of example-2 was subjected to physicochemical studies under different test conditions such as ambient temperature (room temperature) test and at low temperature. The composition of example-2 was subjected to a low temperature test after being held in a refrigerator at 0 ℃ for 7 days, the sample was held in an oven at 54 ℃ for 2 weeks and at 40 ℃ for 8 weeks, and oven stability was performed with accelerated thermal stability (AHS). The composition of example-2 remained a uniform and transparent liquid under all four stability conditions. The density of the composition was kept at 0.993 and the degradation of activity was kept within acceptable limits. The permanent foam in the composition remains within an acceptable range. And the pH of the composition was found to be around 6 under all conditions.
TABLE-4
Example 3: acetamiprid 146+indoxacarb 54 Emulsifiable Concentrate (EC)
Acetamiprid 146+ indoxacarb 54 Emulsifiable Concentrates (ECs) were prepared using the materials in table 5.
TABLE 5
Composition of the components | Quantity (g/l) |
Acetamiprid original drug | 149.00g |
Indoxacarb original drug | 56.84g |
N-butyl pyrrolidone | 350.00g |
Cyclohexanone | 360.00g |
Butyl EO.PO block polymers | 100.00g |
360g of cyclohexanone are charged into a mixing vessel. 350g of n-butylpyrrolidone are added to the same mixing vessel with continuous shaking. 56.84g indoxacarb and 149g acetamiprid were then added with continuous stirring to give a mixture. 100g of butyl EO. PO block polymer and the remaining 60g of cyclohexanone were added to the mixture and mixed for about 30 minutes to give an emulsifiable concentrate.
Stability data
Physicochemical studies were performed on the composition of example-3 under different test conditions, such as environmental (at room temperature) testing, low temperature testing after holding the composition of example-3 in a refrigerator for 7 days at 0 ℃, oven stability after holding the sample in an oven for 2 weeks at 54 ℃ and for 8 weeks at 40 ℃, to accelerate thermal stability (AHS). The composition of example-1 remained a uniform and transparent liquid under all four stability conditions. The density of the composition was kept at 1.02. Degradation of activity is kept within acceptable limits. The permanent foam in the composition remains within an acceptable range. And the pH of the composition was found to be around 5 under all conditions.
TABLE-6
Stability after dilution
The compositions of examples 1-3 were tested for dilution stability, wherein each composition was diluted with standard water to prepare 1% dilution aliquots. The stability of the diluted compositions was evaluated at different time intervals. Further evaluation was performed 24.5 hours after re-emulsifying the composition. This was repeated twice as well. The composition of example-1 remained a uniform and stable liquid throughout all of the above specified time intervals. Similarly, the compositions of examples-2 and-3 remained fairly stable without any significant cream or oil formation.
TABLE-7
Std.H 2 0A represents CIPAC standard water A with hardness of 20 ppm; standard H 2 0D represents CIPAC standard water D with a hardness of 342 ppm.
Screening for solvents and surfactants suitable for stabilizing liquid compositions at Low temperatures
Examples 4-7 are compositions of ME formulations of acetamiprid and emamectin benzoate. Various solvents and surfactants have been tried to prepare liquid compositions based on neonicotinoids that remain stable at low temperatures. The composition was subjected to dilution stability studies according to CIPAC 41.1, wherein the composition was diluted in water and left to stand for 24 hours, after which the number and properties of any separation materials were evaluated. The composition of example-4 was prepared using an anionic/nonionic surfactant mixture having an HLB value of 9.6. Upon dilution stability, 1ml of cream and some oil were observed after 0.5 hours. Therefore, it fails the test and cannot be considered for further stability testing. The composition of example-5 was prepared using dodecylbenzene sulfonate having an HLB of 8.6. BHA remains immiscible in the solvent. The composition failed to form an ME formulation and was therefore found to be unsuitable for low temperature testing. Similarly, the compositions of examples-6 and-7 were prepared using dimethyl sulfoxide (DMSO) and propylene carbonate, respectively. Both compositions showed crystallization in the dilution stability test, indicating that crystals formed when maintained at 0 ℃.
TABLE-8
* Ex=example
The compositions of examples 8-11 are EC compositions comprising acetamiprid and indoxacarb. The composition of example-8 was prepared using an anionic/nonionic surfactant mixture having an HLB value of 9.6. Similarly, the composition of example-9 was prepared using dodecylbenzene sulfonate having an HLB of 8.6. In both compositions, 1ml of oil and 2ml of cream were observed while maintaining dilution stability, and further stability testing was not considered. The compositions of examples-10 and-11 were prepared using dimethyl sulfoxide (DMSO) and propylene carbonate, respectively. Both compositions showed crystallization in the dilution stability test, indicating that crystals formed when maintained at 0 ℃.
Table-9
The compositions of examples 12-15 are SL compositions comprising acetamiprid and indoxacarb. The composition of example-12 was prepared using dodecylbenzene sulfonate having an HLB of 8.6. Similarly, the composition of example-13 was prepared using an anionic/nonionic mixture having an HLB value of 9.6. In both compositions, crystals were observed within 24 hours while maintaining dilution stability. The compositions of examples-14 and-15 were prepared using dimethyl sulfoxide (DMSO) and propylene carbonate, respectively. Both compositions showed crystallization in the dilution stability test, indicating that crystals formed when maintained at 0 ℃.
Table-10
Research on field application
Crop: sweet orange
Test 1 site: leno dard, south africa Lin Bobo province
Test 2 site: mu Yi North south Africa
The compositions of examples-2 and-3 were evaluated for their effectiveness in controlling mealy bugs in citrus. Mealybugs can cause physical damage and appearance damage to citrus fruits, making them unsuitable for export. The composition of example-2 was tested at a dose rate of 54 ml. The composition of example-3 was tested at a dose rate of 36 ml. The effectiveness of the composition was studied against untreated controls. The number of mealy bugs on 25 citrus fruits sampled per block was counted at different time intervals (i.e. 7DAT (days after treatment), 14DAT and 21 DAT). For the compositions of examples-2 and-3, the study was conducted at two different sites (test 1 and test 2). The compositions of example-2 and example-3 were found to control more than 96% mealy bugs at both doses and successfully protected the crop.
Table-11
The compositions of examples-2 and-3 were evaluated for their effectiveness in controlling red spider mites (red mites) on citrus. Red spider mites (p.ulmi) are one of the common pests of citrus and cause damage to old leaves and fruits. The composition of example-2 was tested at a dose rate of 54 ml. The composition of example-3 was tested at a dose rate of 36 ml. The effectiveness of the composition was studied against untreated controls. The number of mites on 30 leaf samples per plot and the control percentage of red spider mites were counted at different time intervals (i.e. 7DAT (days after treatment), 14DAT and 21 DAT). For the compositions of examples-2 and-3, the study was conducted at two different sites (test 1 and test 2). The compositions of example-2 and example-3 were found to control over 90% of the spider mites and successfully protect the crop in both doses and in both trials.
Table-12
Thus, the inventors of the present disclosure successfully stabilized various liquid compositions of neonicotinoid insecticides, alone and in combination with other pesticides, using low polarity amide solvents and surfactants having an HLB range of 10-18. The combination of the low polarity amide solvent and the surfactant having an HLB in the range of about 10 to about 18 successfully stabilizes the neonicotinoid insecticide in the composition and imparts low temperature stability to the composition. Stable liquid compositions also exhibit stability upon dilution. Liquid compositions have been found to be very effective in controlling pests. It should be understood that the present disclosure is not limited to the details of the above-described embodiments, which are described by way of example only.
Claims (19)
1. A liquid agrochemical composition comprising:
(d) At least one neonicotinoid insecticide;
(e) At least one low polarity amide solvent; and
(f) At least one surfactant having an HLB value within the range of from about 10 to about 18.
2. The liquid composition of claim 1, wherein the neonicotinoid insecticide is selected from the group consisting of: acetamiprid, clothianidin, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, and combinations thereof.
3. The liquid composition of claim 1, wherein the composition comprises from about 0.1% w/w to about 90% w/w of the neonicotinoid insecticide based on the total weight of the liquid composition.
4. The liquid composition of claim 1, wherein the low polarity amide solvent comprises N-C 2-8 Alkyl pyrrolidone groups.
5. The liquid composition of claim 1, wherein the composition comprises 0.01% w/w to about 90% w/w of the low polarity amide solvent based on the total weight of the liquid composition.
6. A liquid composition according to claim 1 and claim 3, wherein the low polarity amide solvent is selected from the group consisting of: n-butylpyrrolidone (NBP), n-octylpyrrolidone, and n-ethylpyrrolidone (NEP).
7. The liquid composition of claim 1, wherein the composition comprises from about 0.01% w/w to about 50% w/w of surfactant having an HLB value of from about 10 to about 18, based on the total weight of the liquid composition.
8. The liquid composition of claim 1, wherein the surfactant having an HLB value ranging from about 10 to about 18 is selected from the group consisting of: polyoxyethylene monooleate, polyoxyethylene monostearate, polyoxyethylene monolaurate, sodium oleate, triethanolamine oleate, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monopalmitate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan tristearate, polyoxyethylene sorbitan monooleate, polyoxyethylene sorbitan trioleate, block copolymers of ethylene oxide, propylene oxide, and block copolymers of propylene oxide and propylene glycol.
9. The liquid composition of claim 1, wherein the composition comprises from about 0.1% w/w to about 90% w/w neonicotinoid insecticide, from 0.01% w/w to about 90% w/w low polarity amide solvent, from about 0.01% w/w to about 50% w/w surfactant having an HLB value of from about 10 to about 18, based on the total weight of the liquid composition.
10. The liquid composition of claim 1, wherein the composition is in the form of an emulsifiable concentrate, a soluble liquid, a microemulsion, a suspension concentrate, a suspoemulsion, or an oil dispersion.
11. The liquid agrochemical composition of claim 1 further comprising an additional pesticide.
12. The liquid composition of claim 8, wherein the additional pesticide is selected from the group consisting of: oxadiazine insecticides, avermectin insecticides, thiophosphoramide insecticides, phenylpyrazole insecticides, diamide insecticides, benzoylurea insecticides, pyrethroid insecticides, salts, esters, optically active isomers thereof, and combinations thereof.
13. The liquid composition of claim 11, wherein the additional pesticide is selected from one or more of the group consisting of: indoxacarb, abamectin, emamectin benzoate, ivermectin, acephate, monocrotophos, diflufenican, pyraclostrobin, ethiprole, fipronil, chlorantraniliprole, cyantraniliprole, lufenuron, fluureide, diflubenzuron, bifenthrin, cyhalothrin, lambda-cyhalothrin, fenvalerate and transfluthrin.
14. A liquid agrochemical composition comprising about 1% w/w to 90% w/w acetamiprid, 1% w/w to 40% w/w emamectin benzoate, about 20% w/w to 90% w/w of a low polarity amide solvent comprising n-butyl pyrrolidone, and about 0.1% w/w to 10% w/w of a surfactant having an HLB value in the range of 10-18.
15. A liquid agrochemical composition comprising about 1% to 90% w/w acetamiprid, 1% to 40% w/w indoxacarb, about 20% to 90% w/w of a low polarity amide solvent comprising n-butyl pyrrolidone, and about 0.1% to 10% w/w of a surfactant having an HLB value in the range of 10 to about 18.
16. A method of preparing a liquid agrochemical composition, wherein the method comprises: at least one neonicotinoid insecticide is combined with at least one low polarity amide solvent and at least one surfactant having an HLB value of from about 10 to about 18.
17. A method of controlling pests, the method comprising applying to a plant or to a locus where the plant is growing or is to be planted or to plant propagation material or a locus where it is suitable, a liquid agrochemical composition comprising:
(a) At least one neonicotinoid insecticide;
(b) At least one low polarity amide solvent; and
(c) At least one surfactant having an HLB value of from about 10 to about 18.
18. Use of a liquid agrochemical composition for controlling pests, the liquid agrochemical composition comprising:
at least one neonicotinoid insecticide;
at least one low polarity amide solvent; and
at least one surfactant having an HLB value of from about 10 to about 18.
19. Use of a liquid agrochemical composition for controlling a pest selected from the group consisting of mealybugs and full-claw citrus mites, said liquid agrochemical composition comprising:
at least one neonicotinoid insecticide;
at least one low polarity amide solvent; and
at least one surfactant having an HLB value of from about 10 to about 18.
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IN202121010121 | 2021-03-10 | ||
IN202121010121 | 2021-03-10 | ||
PCT/EP2022/056258 WO2022189592A1 (en) | 2021-03-10 | 2022-03-10 | Liquid composition comprising a neonictonoid |
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CN (1) | CN117560993A (en) |
AR (1) | AR125069A1 (en) |
AU (1) | AU2022231890A1 (en) |
CO (1) | CO2023013308A2 (en) |
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CN105580830A (en) * | 2014-10-22 | 2016-05-18 | 陕西美邦农药有限公司 | Insecticidal composition containing ZJ3757 |
CN105638714A (en) * | 2014-11-13 | 2016-06-08 | 陕西美邦农药有限公司 | Insecticidal composition containing wufuchongzong |
DE102016210164A1 (en) * | 2016-06-08 | 2017-12-14 | Clariant International Ltd | Use of N-substituted pyrrolidones to promote the penetration of agrochemical active ingredients |
CN108782585A (en) * | 2017-04-28 | 2018-11-13 | 江苏龙灯化学有限公司 | A kind of water-dispersed composition containing avermectin and Acetamiprid |
CN110477000A (en) * | 2019-09-19 | 2019-11-22 | 山东省林业科学研究院 | A kind of liquid formulation for trunk injection and its preparation method and application of Japanese red pine limb portion pest |
CN111084190A (en) * | 2019-12-04 | 2020-05-01 | 河北威远生物化工有限公司 | Insecticidal composition containing emamectin benzoate B2a and application thereof |
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AR125069A1 (en) | 2023-06-07 |
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