ZA200509284B - Insecticidal composition - Google Patents
Insecticidal composition Download PDFInfo
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- ZA200509284B ZA200509284B ZA200509284A ZA200509284A ZA200509284B ZA 200509284 B ZA200509284 B ZA 200509284B ZA 200509284 A ZA200509284 A ZA 200509284A ZA 200509284 A ZA200509284 A ZA 200509284A ZA 200509284 B ZA200509284 B ZA 200509284B
- Authority
- ZA
- South Africa
- Prior art keywords
- surfactant
- insecticidal composition
- solvent
- weight
- composition according
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 27
- 230000000749 insecticidal effect Effects 0.000 title claims description 17
- -1 chloronicotinyl compound Chemical class 0.000 claims description 25
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 24
- 239000004094 surface-active agent Substances 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 16
- 239000007788 liquid Substances 0.000 claims description 13
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 10
- 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 8
- 239000005875 Acetamiprid Substances 0.000 claims description 8
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 8
- 239000004359 castor oil Substances 0.000 claims description 6
- 235000019438 castor oil Nutrition 0.000 claims description 6
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 5
- 229920001400 block copolymer Polymers 0.000 claims description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000012046 mixed solvent Substances 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 239000005906 Imidacloprid Substances 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- YWTYJOPNNQFBPC-UHFFFAOYSA-N imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 description 3
- 229940056881 imidacloprid Drugs 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical class CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 1
- TVFWYUWNQVRQRG-UHFFFAOYSA-N 2,3,4-tris(2-phenylethenyl)phenol Chemical compound C=1C=CC=CC=1C=CC1=C(C=CC=2C=CC=CC=2)C(O)=CC=C1C=CC1=CC=CC=C1 TVFWYUWNQVRQRG-UHFFFAOYSA-N 0.000 description 1
- DYBIGIADVHIODH-UHFFFAOYSA-N 2-nonylphenol;oxirane Chemical compound C1CO1.CCCCCCCCCC1=CC=CC=C1O DYBIGIADVHIODH-UHFFFAOYSA-N 0.000 description 1
- FOGYNLXERPKEGN-UHFFFAOYSA-N 3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfopropyl)phenoxy]propane-1-sulfonic acid Chemical class COC1=CC=CC(CC(CS(O)(=O)=O)OC=2C(=CC(CCCS(O)(=O)=O)=CC=2)OC)=C1O FOGYNLXERPKEGN-UHFFFAOYSA-N 0.000 description 1
- 244000208060 Lawsonia inermis Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- HWQXBVHZYDELQG-UHFFFAOYSA-L disodium 2,2-bis(6-methylheptyl)-3-sulfobutanedioate Chemical compound C(CCCCC(C)C)C(C(C(=O)[O-])S(=O)(=O)O)(C(=O)[O-])CCCCCC(C)C.[Na+].[Na+] HWQXBVHZYDELQG-UHFFFAOYSA-L 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical class NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
op 19h
INSECTICIDAL COMPOSITION
The present invention relates to a water-soluble solution which evenly dissolves in water and exhibites excellent insecticidal activity, and particularly relates to a water-soluble solution containing as its active ingredient a chloronicotinyl compound such as acetamiprid.
Although emulsions, wettable powders, flowable agents, or the like can be raised among agricultural chemical formulations as examples of formulations that are to be diluted with water before spraying, a method for formulation of a water-soluble agent in which an active ingredient is dissolved in a polar solvent which readily dissolves in water is preferred due to easy handling thereof. As a water-soluble agent containing a chloronicotinyl compound as a bioactive ingredient, Japanese
Laid-Open Patent Application No. Hei 8-92091, for example, discloses a formulation in which a chloronicotinyl insecticide such as imidacloprid is formulated with a solvent such as ethanol, butanol, glycerol, hydrocarbons, polyethylene glycol,
N-methylpyrrolidone, or the like in a concentrated solution which is to be diluted before application, and more specifically discloses a water-soluble concentrated (SL) formulation using imidacloprid with a natural emulsifier based on an alkylaryl polyglycol ether or sodium diisooctyl sulfosuccinate as a surfactant, and dimethyl sulfoxide and isopropanol as polar solvents.
Moreover, Published Japanese Translation No. 2001-50665 of PCT International Publication discloses as a formulation of a compound having insecticidal activity a water-soluble agent using a nonyl phenol ethylene oxide concentrated solution, and a concentrated solution of N-methylpyrrolidone or tristyryl phenol ethylene oxide, 70% W/W solution of calcium dodecylbenzene sulfonate, N-methylpyrrolidone, and Solvesso.
However, the above-mentioned compositions are insufficiently stable at low temperature and have problems with the handling thereof in a state of concentrated solution, and the activity thereof is also insufficient.
The present invention has as its object to provide a water-soluble solution of chloronicotinyl insecticide which puts less burden on the environment and has excellent effects.
As a result of conducting extensive studies to solve the aforementioned problems, the inventors of the present invention found that the aforementioned problems could be solved by using an organic solvent which is a mixed solvent containing dimethyl sulfoxide and either dimethylacetamide or y-butyrolactone, and additionally by combining a particular surfactant, thereby leading to completion of the present invention.
Specifically, the present invention relates to the following:
[1] a liquid insecticidal composition characterized by comprising: (1) a chloronicotinyl compound; (2) a solvent comprsing dimethyl sulfoxide and either dimethylacetamide or y-butyrolactone; and (3) a surfactant;
[2] a liquid insecticidal composition according to [1] characterized in that the surfactant is a castor oil surfactant or a propylene oxide / ethylene oxide block copolymer surfactant;
[3] a liquid insecticidal composition according to [1] or [2] characterized in that the chloronicotinyl compound is acetamiprid;
[4] a liquid insecticidal composition according to any one of
[1] to [3] characterized in that the chloronicotinyl compound (1) is contained in an amount of 1.5 to 40% by weight, the solvent (2) is contained in an amount of 59.9 to 98.4% by weight, and the surfactant (3) is contained in an amount of 0.1 to 10% by weight;
[5] a liquid insecticidal composition according to any one of
[1] to [4] characterized in that the weight ratio of dimethyl sulfoxide to either dimethylacetamide or y-butyrolactone in the solvent is in the range of 10:90 to 90:10; and
[6] a liquid insecticidal composition according to any one of
[1] to [5] characterized in that the solvent comprises 2 to 40% by weight of N-methylpyrrolidone relative to the whole solvent.
The chloronicotinyl compound to be used in the present invention is not particularly limited, provided that it has a chloronicotinyl group or exhibits similar bioactivity, and the following compounds can be specifically raised as examples.
— CH, 7 \ _ 7 / lo] CH7—N__-NH Ci CH—N_ NH,
SA GE
~N
NO, N—NO,
CH, a a Hon SS = CH, cl NO
Sno, 2 » I
OC. H o— crn i A ee
N= S—CH—CH,
N
Neen ~
NO, CH,
C.Hs 7 \ A. TR /
Cl CH;—N.__NH cl CH; ——N NHCH,
CTL TTY
~
CN N—NO,
o—0 Hon S oi Hon s
SAEs SEER Sa
Nen N—NO, ( re o— Hone NH a— Horn N(CH,),
N= hy N=
CH_
NO, CH—NO, cr a—{ Hn NH o— Horn N(CH;), = " \
CH
“No, N——NO, re
Gt MN eo Hcnni—c—on, o— cnn N—CH,
I TTY fa SY
CN ~
NO,
i ro oi H—ctn—g—non, c— NN cH—n N—CH
N= 1 _ 2 Ne” 3
CH_ N I
NC,
Ss NH S HENNA
Y a
CH N N
NO,
NO,
H,C N._ NH S CH —N._ _NH 4
NO,
Among them, acetamiprid is particularly preferable.
The solvent usable in the present invention is a mixed solvent containing dimethyl sulfoxide and at least one selected from the group consisting of dimethylacetamide and y-butyrolactone. Although the mixing ratio thereof is not particularly limited, provided that it is within a range which enables the chloronicotinyl compound to be dissolved, it is specifically preferable that the ratio by weight of dimethyl sulfoxide to at least one selected from the group consisting of dimethylacetamide and y-butyrolactone be in a range of 10:90 to 90:10. Although other solvents such as ethanol, butanol, benzyl alcohol, glycerol, hydrocarbons, propylene glycol, polyethylene glycol, N-methylpyrrolidone, or the like may be optionally added, if needed, N-methylpyrrolidone is preferably used to improve the stability of the chloronicotinyl compound at low temperature. Although the content of
N-methylpyrrolidone is not particularly limited, it is preferably within a range of 2 to 40% by weight of the whole solvent in view of handling convenience.
Specific examples of the surfactant usable in the present invention include ionic or nonionic emulsions, dispersants, wetting agents, and mixtures thereof. Particular examples thereof include salts of polyacrylic acid, salts of lignosulfonic acid, salts of phenolsulfonic acid or naphthalenesulfonic acid, condensed polymers of ethylene oxide and fatty alcohol or fatty acid, fatty acid ester, or fatty acid amino, substituted phenols (particularly alkylphenol or arylphenol), sulfosuccinate ester, taurine derivatives (particularly alkyltaurate), phosphoric esters of condensed polymers of alcohol or phenol and ethylene oxide, esters of fatty acid and polyol, sulfates, derivatives having a functional group of sulfonate or phosphate of the above-mentioned compound, and the like. Preferable examples thereof include castor oil surfactants, and propylene oxide / ethylene oxide block copolymer surfactants.
Although the mixing ratio of the chloronicotinyl compound, the solvent and the surfactant in the liquid insecticidal composition of the present invention is not particularly limited, it is specifically preferable that the chloronicotinyl compound be contained in an amount of 1.5 to 40% by weight, the solvent be contained in an amount of 59.9 to 98.4% by weight, and the surfactant be contained in an amount of 0.1 to 10% by weight.
Although the following provides a specific explanation of effects of the present invention through examples, the present invention is not limited to these examples.
Example 1 g of acetamiprid was dissolved in a mixed solvent containing 37.5 g of dimethylacetamide and 37.5 g of dimethyl sulfoxide, and 5 g of polyoxyethylene castor oil (HLB 11.7) was further dissolved in the mixture as a surfactant to obtain a uniform solution.
Example 2
20 g of acetamiprid was dissolved in a mixed solvent containing 37.5 g of y-butyrolactone and 37.5 g of dimethyl sulfoxide, and 5 g of polyoxyethylene hydrogenated castor oil (HLB 10.8) was further dissolved in the mixture as a surfactant to obtain a uniform solution.
Example 3 20 g of acetamiprid was dissolved in a mixed solvent containing 37.5 g of y-butyrolactone and 41.5 g of dimethyl sulfoxide, and 1 g of PO/EO block copolymer (HLB 12 to 18: manufactured by BASF under the name of Pluronic PE 6400) was further dissolved in the mixture as a surfactant to obtain a uniform solution.
Example 4 20 g of imidacloprid was dissolved in a mixed solvent containing 37.5 g of dimethylacetamide and 37.5 g of dimethyl sulfoxide, and 5 g of polyoxyethylene castor oil was further dissolved in the mixture as a surfactant to obtain a uniform solution.
Example 5 20 g of acetamiprid was dissolved in a mixed solvent containing 27.5 g of dimethylacetamide, 37.5 g of dimethyl
Claims (6)
1. A liquid insecticidal composition comprising: (1) a chloronicotinyl compound; (2) a solvent comprising dimethyl sulfoxide and either dimethylacetamide or y-butyrolactone; and (3) a surfactant.
2. A liquid insecticidal composition according to claim 1, wherein the surfactant is a castor oil surfactant or a propylene oxide / ethylene oxide block copolymer surfactant.
3. A liquid insecticidal composition according to claim 1 or 2, wherein the chloronicotinyl compound is acetamiprid.
4. A liquid insecticidal composition according to any one of claims 1 to 3, wherein the chloronicotinyl compound (1) is contained in an amount of 1.5 to 40% by weight, the solvent (2) is contained in an amount of 59.9 to 98.4% by weight, and the surfactant (3) is contained in an amount of 0.1 to 10% by weight.
5. A liquid insecticidal composition according to any one of claims 1 to 4, wherein the ratio of dimethyl sulfoxide to either dimethylacetamide or y-butyrolactone in the solvent is in a range of 10:90 to 90:10.
6. A liquid insecticidal composition according to any one of claims 1 to 5, wherein the solvent comprises 2 to 40% by weight of N-methylpyrrolidone relative to the whole solvent.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2003140022 | 2003-05-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200509284B true ZA200509284B (en) | 2007-03-28 |
Family
ID=36788717
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200509284A ZA200509284B (en) | 2003-05-19 | 2004-05-18 | Insecticidal composition |
Country Status (3)
| Country | Link |
|---|---|
| CN (1) | CN100435638C (en) |
| TN (1) | TNSN05289A1 (en) |
| ZA (1) | ZA200509284B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5092429B2 (en) * | 2007-01-31 | 2012-12-05 | 住友化学株式会社 | Pesticide solution containing hydrophobic agrochemical active compound |
| JP5125126B2 (en) * | 2007-01-31 | 2013-01-23 | 住友化学株式会社 | Pesticide solution containing hydrophobic agrochemical active compound |
| JP6765436B2 (en) * | 2016-03-17 | 2020-10-07 | ダウ グローバル テクノロジーズ エルエルシー | Emulsifying concentrate |
| CN108552168A (en) * | 2018-06-02 | 2018-09-21 | 允发化工（上海）有限公司 | A kind of high stability imidacloprid liquor |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1297681A (en) * | 1999-11-26 | 2001-06-06 | 王海玉 | Miticide composition of diesel oil and acetamiprid |
| CN1292223A (en) * | 2000-10-15 | 2001-04-25 | 张业生 | Pesticide composition containing acetamide |
| DE10118076A1 (en) * | 2001-04-11 | 2002-10-17 | Bayer Ag | Using fatty alcohol ethoxylate as penetration enhancer for neonicotinyl insecticide, useful for plant protection, are effective at very low concentration |
-
2004
- 2004-05-18 CN CNB2004800134265A patent/CN100435638C/en not_active Expired - Lifetime
- 2004-05-18 ZA ZA200509284A patent/ZA200509284B/en unknown
-
2005
- 2005-11-14 TN TNP2005000289A patent/TNSN05289A1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| TNSN05289A1 (en) | 2007-07-10 |
| CN100435638C (en) | 2008-11-26 |
| CN1791332A (en) | 2006-06-21 |
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