IL146103A - Aqueous pesticide containing a diguanidinium alkybenzenesulfonate derivative - Google Patents
Aqueous pesticide containing a diguanidinium alkybenzenesulfonate derivativeInfo
- Publication number
- IL146103A IL146103A IL146103A IL14610301A IL146103A IL 146103 A IL146103 A IL 146103A IL 146103 A IL146103 A IL 146103A IL 14610301 A IL14610301 A IL 14610301A IL 146103 A IL146103 A IL 146103A
- Authority
- IL
- Israel
- Prior art keywords
- aqueous suspension
- alkyl group
- pesticide preparation
- surfactant
- parts
- Prior art date
Links
- 239000000575 pesticide Substances 0.000 title claims description 111
- 238000002360 preparation method Methods 0.000 claims description 80
- 239000007900 aqueous suspension Substances 0.000 claims description 68
- 239000000725 suspension Substances 0.000 claims description 50
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 34
- 239000002245 particle Substances 0.000 claims description 32
- 150000003904 phospholipids Chemical class 0.000 claims description 29
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 28
- 229910052740 iodine Inorganic materials 0.000 claims description 28
- 239000011630 iodine Substances 0.000 claims description 28
- 239000004094 surface-active agent Substances 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 23
- 102000004169 proteins and genes Human genes 0.000 claims description 17
- 108090000623 proteins and genes Proteins 0.000 claims description 17
- 239000007983 Tris buffer Substances 0.000 claims description 14
- 229940077388 benzenesulfonate Drugs 0.000 claims description 14
- RONFGUROBZGJKP-UHFFFAOYSA-N iminoctadine Chemical compound NC(N)=NCCCCCCCCNCCCCCCCCN=C(N)N RONFGUROBZGJKP-UHFFFAOYSA-N 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims description 5
- 238000007561 laser diffraction method Methods 0.000 claims 1
- 238000000790 scattering method Methods 0.000 claims 1
- 239000004615 ingredient Substances 0.000 description 40
- 238000003860 storage Methods 0.000 description 32
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 30
- -1 alkylbenzene sulfonate Chemical class 0.000 description 28
- 238000012360 testing method Methods 0.000 description 24
- 235000018102 proteins Nutrition 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 15
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 11
- XAYMVFWOJIOUTA-UHFFFAOYSA-N 2-[8-[8-(diaminomethylideneamino)octylamino]octyl]guanidine;2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O.NC(N)=NCCCCCCCCNCCCCCCCCN=C(N)N XAYMVFWOJIOUTA-UHFFFAOYSA-N 0.000 description 9
- 239000008240 homogeneous mixture Substances 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical class CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 8
- 229940070765 laurate Drugs 0.000 description 8
- 238000011084 recovery Methods 0.000 description 8
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 7
- 239000002736 nonionic surfactant Substances 0.000 description 7
- 102000011632 Caseins Human genes 0.000 description 6
- 108010076119 Caseins Proteins 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical class C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 5
- 229940099578 hydrogenated soybean lecithin Drugs 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 150000005215 alkyl ethers Chemical class 0.000 description 4
- 239000007798 antifreeze agent Substances 0.000 description 4
- 239000005018 casein Substances 0.000 description 4
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 4
- 235000021240 caseins Nutrition 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 230000007774 longterm Effects 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 102000002322 Egg Proteins Human genes 0.000 description 3
- 108010000912 Egg Proteins Proteins 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- MMQZBEXYFLXHEN-UHFFFAOYSA-N OCC(O)CO.OCC(O)CO.OCC(O)CO.OCC(O)CO.OCC(O)CO.OCC(O)CO.CCCCCCCCCCCCCCCCCC(O)=O Chemical compound OCC(O)CO.OCC(O)CO.OCC(O)CO.OCC(O)CO.OCC(O)CO.OCC(O)CO.CCCCCCCCCCCCCCCCCC(O)=O MMQZBEXYFLXHEN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000003945 anionic surfactant Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 229940083466 soybean lecithin Drugs 0.000 description 3
- 238000013112 stability test Methods 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical class CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-UHFFFAOYSA-N 0.000 description 2
- FDCJDKXCCYFOCV-UHFFFAOYSA-N 1-hexadecoxyhexadecane Chemical class CCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCC FDCJDKXCCYFOCV-UHFFFAOYSA-N 0.000 description 2
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
- OADIZUFHUPTFAG-UHFFFAOYSA-N 2-[2-(2-ethylhexoxy)ethoxy]ethanol Chemical compound CCCCC(CC)COCCOCCO OADIZUFHUPTFAG-UHFFFAOYSA-N 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000005210 alkyl ammonium group Chemical group 0.000 description 2
- 150000008051 alkyl sulfates Chemical class 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 210000002969 egg yolk Anatomy 0.000 description 2
- 235000013345 egg yolk Nutrition 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 230000009969 flowable effect Effects 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 239000002563 ionic surfactant Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229940080237 sodium caseinate Drugs 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 230000008023 solidification Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- JQWAHKMIYCERGA-UHFFFAOYSA-N (2-nonanoyloxy-3-octadeca-9,12-dienoyloxypropoxy)-[2-(trimethylazaniumyl)ethyl]phosphinate Chemical compound CCCCCCCCC(=O)OC(COP([O-])(=O)CC[N+](C)(C)C)COC(=O)CCCCCCCC=CCC=CCCCCC JQWAHKMIYCERGA-UHFFFAOYSA-N 0.000 description 1
- CUVLMZNMSPJDON-UHFFFAOYSA-N 1-(1-butoxypropan-2-yloxy)propan-2-ol Chemical compound CCCCOCC(C)OCC(C)O CUVLMZNMSPJDON-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- OHJYHAOODFPJOD-UHFFFAOYSA-N 2-(2-ethylhexoxy)ethanol Chemical compound CCCCC(CC)COCCO OHJYHAOODFPJOD-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
- QCVGEOXPDFCNHA-UHFFFAOYSA-N 5,5-dimethyl-2,4-dioxo-1,3-oxazolidine-3-carboxamide Chemical compound CC1(C)OC(=O)N(C(N)=O)C1=O QCVGEOXPDFCNHA-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- 108010082495 Dietary Plant Proteins Proteins 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 102000014171 Milk Proteins Human genes 0.000 description 1
- 108010011756 Milk Proteins Proteins 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 108010009736 Protein Hydrolysates Proteins 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 108010046377 Whey Proteins Proteins 0.000 description 1
- 102000007544 Whey Proteins Human genes 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 235000021120 animal protein Nutrition 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001351 cycling effect Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- AOLMPVPUFVWGPN-UHFFFAOYSA-N diazanium;1-dodecoxydodecane;sulfate Chemical compound [NH4+].[NH4+].[O-]S([O-])(=O)=O.CCCCCCCCCCCCOCCCCCCCCCCCC AOLMPVPUFVWGPN-UHFFFAOYSA-N 0.000 description 1
- KSNWDIGDTRPVGZ-UHFFFAOYSA-N dodecanoic acid;propane-1,2,3-triol Chemical compound OCC(O)CO.OCC(O)CO.OCC(O)CO.OCC(O)CO.OCC(O)CO.OCC(O)CO.OCC(O)CO.OCC(O)CO.OCC(O)CO.OCC(O)CO.CCCCCCCCCCCC(O)=O KSNWDIGDTRPVGZ-UHFFFAOYSA-N 0.000 description 1
- SYELZBGXAIXKHU-UHFFFAOYSA-N dodecyldimethylamine N-oxide Chemical compound CCCCCCCCCCCC[N+](C)(C)[O-] SYELZBGXAIXKHU-UHFFFAOYSA-N 0.000 description 1
- 235000014103 egg white Nutrition 0.000 description 1
- 210000000969 egg white Anatomy 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000413 hydrolysate Substances 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000021239 milk protein Nutrition 0.000 description 1
- 229940105132 myristate Drugs 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- VUWDAOLDXOYMIZ-UHFFFAOYSA-N nonadecan-1-amine;hydrochloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCCC[NH3+] VUWDAOLDXOYMIZ-UHFFFAOYSA-N 0.000 description 1
- RXDBYIXFAFDTHT-UHFFFAOYSA-N o-dodecylhydroxylamine Chemical compound CCCCCCCCCCCCON RXDBYIXFAFDTHT-UHFFFAOYSA-N 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 235000020183 skimmed milk Nutrition 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical group OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical group 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 235000021119 whey protein Nutrition 0.000 description 1
- 235000008939 whole milk Nutrition 0.000 description 1
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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/22—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing ingredients stabilising the active ingredients
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
-
- 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
- A01N47/42—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 containing —N=CX2 groups, e.g. isothiourea
- A01N47/44—Guanidine; Derivatives thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Toxicology (AREA)
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
AN AQUEOUS PESTICIDE CONTAINING A DIGUANIDINIUM ALKYBENZENESULFONATE DERIVATIVE TECHNICAL FIELD The present invention relates to a pesticide preparation of the aqueous suspension type (hereinafter referred to as an aqueous suspension pesticide preparation) which contains 1,1'- iminiodi (octamethylene) diguanidinium tris (alkylbenzenesulfonate) as an active pesticide ingredient, the pesticide preparation having excellent stability even under fluctuating low temperature conditions.
BACKGROUND ART 1, 1' -Iminiodi (octamethylene) diguanidinium tris (alkylbenzenesulfonate) , which is the active pesticide ingredient of the preparation according to the present invention, is known (Japanese Examined Patent Application, Second Publication No. Hei 2-7564; U.S. Patent No. 4,659,739) as an excellent fungicide for agricultural and horticultural use. Among variants thereof, a C10 to C13 1,1'-iminiodi (octamethylene) diguanidinium tris (alkylbenzenesulfonate) (melting point: 92 to 96°C), which contains as the major component a Ci2 component of an alkyl chain of an alkylbenzene sulfonate, is called i inoctadine tris ( albesilate) , and they have already been put into practical use as bread-spectrum fungicides.
A pesticide proper, which is in the form of a solid at ordinary temperatures, may typically be processed into an aqueous suspension pesticide preparation by blending a water-soluble or water-suspendible synthetic polymer compound, an anionic surfactant, a nonionic surfactant, etc., therewith.
When the pesticide proper has a melting point of from 30 to 100 °C, however, there arises a problem in that if a suspension preparation which is a suspension of the pesticide proper is put under a condition in which the temperature fluctuates largely, the suspension breaks while crystals develop due to the melting or solidification of the solid pesticide proper which has been dispersed. In the case of an emulsified aqueous suspension prepared by dissolving the pesticide proper in a commonly used water-insoluble organic solvent and emulsifying in water, on the other hand, there arises another problem in that the emulsion breaks while crystals are precipitated because the pesticide proper crystallizes in fine liquid droplets dispersed in water.
According to a conventional known method of processing the pesticide proper into a preparation, it was difficult to process the pesticide into a stable aqueous suspension preparation because of severe crystal precipitation of 1,1'-iminiodi (octamethylene) diguanidinium tris (alkvlbenzenesulfonate) , which is the active pesticide ingredient used in the present invention. In the aqueous suspension thus obtained, the suspension breaks due to solidification or crystallization of the active pesticide ingredient. It was difficult to emulsify the active pesticide ingredient because the active pesticide ingredient has very poor solubility in commonly used water-insoluble organic solvents.
To solve these problems, the present inventors developed an aqueous suspension pesticide preparation which includes (a) a 1, 1' -iminiodi (octamethylene) diguanidinium tris (alkyl-benzenesulfonate) ; (b) a compound represented by the general formula (1) : R-O- (CH2CH20)n-H (wherein R represents an alkyl group or alkenyl group having 8 to 18 carbon atoms and n represents an integer of 0 to 4) as a suspension stabilizer, or a phospholipid; (c) a surfactant having a C6 - C2o alkyl or alkenyl group; and (e) water, as described in Japanese Unexamined Patent Application, First Publication No. Hei 8-225402 (U.S. Patent No. 5,728,734).
It is believed that this aqueous suspension pesticide preparation is an aqueous suspension pesticide preparation which has excellent stability and excellent safety for the environment and users, because it maintains a stable suspension state without separating and precipitating the active pesticide ingredient after long-term storage tests at 50°C, long-term storage tests at -5°C, and long-term storage tests for 12 weeks under conditions with severe fluctuations in temperature, specifically a long-term cycling storage test with a high temperature (50°C) for 3 days and a low temperature (-10°C) for 3 days.
However, it became apparent that the preparation has poor resistance to changes in temperature at low temperatures.
That is, in the winter in a cold district, the day and night-temperatures fluctuate between 5 and -10 °C, and the fluctuation continues cyclically from day to day; when the preparation was stored for a long period in this state in the winter, the viscosity of the preparation increased while the suspended state was maintained, or the preparation solidified into the form of a cream and did not recover a good flowable state until the temperature increased to about 20 °C in the spring. Even though the preparation returned to a flowable state, the suspension state degraded. As a result, microprecipitates of the active pesticide ingredient are produced in the suspension, thereby causing clogging of applicators, and thus making it difficult to spray the preparation .
As described above, it was difficult to say that the storage stability of the aqueous suspension pesticide preparation of 1, 1' -iminiodi (octamethylene) diguanidinium tris (alkylbenzenesulfonate) , which has previously been developed, is satisfactory in the winter when the temperature repeats cycles at low temperatures around 0°C.
DISCLOSURE OF INVENTION Accordingly, an object of the present invention is to provide an aqueous suspension pesticide preparation of 1,1'-iminiodi (octamethylene) diguanidinium tris (alkyl- benzenesulfonate) , which not only has excellent storage stability under storage conditions where the temperature changes drastically in a long cycle through the seasons, but also has excellent storage stability during storage in winter when the day and night short-cycle temperatures fluctuate between 5 and -10 °C.
The present inventors have intensively researched to solve the problems described above and have found that it is possible to prepare an aqueous suspension pesticide preparation having excellent storage stability, which can maintain a stable suspension state and inhibit production of microprecipitates of the active pesticide ingredient not only under storage conditions where the temperature changes drastically in a long cycle through the seasons, but also under storage conditions where the temperature changes within a range from 5 to -10 °C in a short cycle through day and night, by using a hydrogenated phospholipid having an iodine value of 20 or less as the phospholipid in the formulation described previously. Thus, the present invention has been completed.
To solve the problems described above, the present invention provides an aqueous suspension pesticide preparation which includes (a) a 1, 1' -iminiodi (octamethylene) diguanidinium tris (alkyl-benzenesulfonate) ; (b) a compound represented by the general formula (1) : R-O- (CH2CH20) n-H (wherein R represents a C - Cis alk l group and n represents an integer of 0 to 4); (c) a phospholipid; (d) a surfactant carrying an alkyl group having 6 to 20 carbon atoms; and (e) water; wherein the phospholipid (c) is a hydrogenated phospholipid having an iodine value of 20 or less.
BEST MODE FOR CARRYING OUT THE INVENTION Each constituent ingredient in the aqueous suspension pesticide preparation of the present invention will be described below.
The 1,1' -iminiodi (octamethylene) diguanidinium tris (alkylbenzenesulfonate) (a) used in the present invention is an active pesticide ingredient of the aqueous suspension - pesticide preparation (hereinafter referred to as an active pesticide ingredient (a) ) .
The alkylbenzenesulfonate, which constitutes the active pesticide ingredient (a) used in the present invention, is preferably benzene sulfonate having a Ci - C2o alkyl group, more preferably benzene sulfonate having a C4 - Ci8 alkyl group, and most preferably benzene sulfonate having a CIQ - C13 alkyl group, in view of prevention of pesticide injury and in view of pesticidal effects. All active pesticide ingredients (a) are substantially insoluble in water. The 1,1'- iminiodi (octamethylene) diguanidinium tris (alkylbenzenesulfonate) , which is a benzene sulfonate having a C10 - C13 alkyl group as an alkyl benzene sulfonate, is an active pesticide ingredient referred to as "iminoctadine tris (albesilate) ".
Next, the compound (b) represented by the general formula (1) will be described.
The compound (b) represented by the general formula (1) used in the present invention acts as a suspension stabilizer in the aqueous suspension pesticide preparation of the present invention .
The compound of the general formula (1) in which n is 0 is a C8 -Ci8 saturated aliphatic alcohol having no oxyethylene group in the molecule.
• The compound of the general formula (1) in which n is 1 is an alcohol in which ethylene glycol is bonded to a Ca -Ci8 saturated aliphatic alcohol via an ether bond, and is generally called a polyoxyethylene (1 mol) monoalkyl ether or simply called a polyoxyethylene (1 mol) alkyl ether. The alcohol of the general formula (1) in which n is 3 means an alcohol in which triethylene glycol is bonded to a saturated aliphatic alcohol via an ether bond, and is generally called a polyoxyethylene (3 mol) alkyl ether.
The Ca -Ci8 saturated aliphatic alcohol may be either a linear or branched one, but a linear one is preferable. It is preferable that the number of carbon atoms of the alkyl group be one which is almost the same as that of the alkyl group of alkylbenzene sulfonate which constitutes the active pesticide ingredient (a) . It is more preferable that the number of carbon atoms be from 10 to 13.
Examples of the saturated aliphatic alcohol represented by the general formula (1) include linear alkanols such as octanol, decyl alcohol, lauryl alcohol, cetyl alcohol and stearyl alcohol; branched alkyl alcohols such as 2-ethyl-hexyl alcohol and 2-ethyl-hexyl diglycol (also known as diethylene glycol mono-2-ethylhexyl ether) ; and polyoxyethylene alkyl ethers in which the number of repetition of the polyoxyethylene moieties is 1 to 4, such as polyoxyethylene (1 - 4 mol) lauryl ethers and polyoxyethylene (1 - 4 mol) cetyl ethers .
Next, the hydrogenated phospholipid (c) having an iodine value of 20 or less used in the present invention will be described.
The hydrogenated phospholipid (c) having an iodine value of 20 or less used in the present invention acts as a suspension stabilizer in the aqueous suspension pesticide preparation of the present invention.
The hydrogenated phospholipid is obtained by hydrogenating lecithin produced from oil seeds (such as soybean and rapeseed) or from animal lipids (such as egg yolk) until the iodine value reaches 20 or less, thereby converting almost all of the unsaturated fatty acid moieties of the phospholipids into saturated fatty acids. The hydrogenated phospholipid having an iodine value of 10 or less is a material which is particularly preferably used in the present invention.
Among these hydrogenated phospholipids, hydrogenated soybean lecithin is particularly preferable in view of cost and because the quality thereof does not greatly vary even though it is made from a natural product.
The hydrogenated phospholipid (c) having an iodine value of 20 or less used in the present invention, especially a hydrogenated lecithin and a water-soluble protein have been widely used in the fields of cosmetics and foods, and it has already been confirmed that they are very safe to the environment and to humans. With respect to the compound represented by the general formula (1) used in the present invention, the safety of the aqueous suspension pesticide preparation can be enhanced by selecting and using ingredients used in the fields of cosmetics and foods. Both of these types of ingredients function as suspension stabilizers in the aqueous suspension pesticide preparation of the active pesticide ingredient.
Next, the surfactant (d) having a C6 - C2o alkyl group used in the' present invention will be described.
The surfactant (d) having a C6 - C2o alkyl group used in the present invention may be either an ionic surfactant or nonionic surfactant. The alkyl group, which is a part of the surfactant, may be either a linear or branched group, but a linear group is preferable. It is preferable that the number of carbon atoms of the alkyl group which is a part of the surfactant be one which is very similar to that of the alkyl group of the alkylbenzene sulfonate which constitutes the active pesticide ingredient (a) . An alkyl group having 10 to 18 carbon atoms is preferable, and an alkyl group having 10 to 13 carbon atoms is more preferable.
It is preferable that the number of carbon atoms of the alkyl group of the compound (b) represented by the general formula (1) used in the present invention and the alkyl group, which constitutes the surfactant having a Ce - C20 alkyl group, be those which are very similar to those of the alkyl group of the alkylbenzene sulfonate which constitutes the active pesticide ingredient (a) . An alkyl group having 10 to 13 carbon atoms is particularly preferable.
Since the raw material used in the surfactant (d) having a C6 - C2o alkyl group is generally made from natural products and the number of carbon atoms of the alkyl group has a distribution range, a surfactant having a Ce - C2o alkyl group can be used as long as it has a C10 - Ci8 alkyl group within a preferable distribution range.
The surfactant (d) having a C6 - C20 alkyl group used in the present invention is roughly classified into (d-1) nonionic surfactants of the polyalkylene oxide type, (d-2) nonionic surfactants of the fatty acid ester type, (d-3) anionic surfactants,
Examples of the nonionic surfactant (d-1) of the polyalkylene oxide type include polyoxyalkylene alkyl ethers such as polyoxyethylene (20 mol) lauryl ether and polyoxyethylene (15 mol) cetyl ether; and polyoxyalkylene alkylamino ethers such as polyoxyethylene (12 mol) laurylamino ether .
Examples of the nonionic surfactant of fatty acid ester type (d-2) include polyglycerin saturated fatty acid esters such as decaglycerin laurate, decaglycerin myristate and hexaglycerin stearate; polyalkylene glycol saturated fatty acid esters such as polyethylene glycol (average molecular weight: 600) laurate; and polyoxyalkylene polypropylene glycol saturated fatty acid esters such as polyoxyethylene polypropylene glycol block copolymer stearate.
Examples of the anionic surfactant (d-3) include alkyl sulfates such as sodium lauryl sulfate; and polyoxyalkylene alkyl sulfates such as polyoxyethylene (20 mol) lauryl ether sulfate ammonium salt.
Examples of the cationic surfactant (d-4) include alkylammonium salts such as cetyltrimethylammonium chloride; and polyoxyalkylene alkylammonium salts such as polyoxyethylene (10 mol) stearylmethylammonium chloride.
Examples of the ampholytic surfactant (d-5) include alkylbetaines such as lauryldimethylammoniobetaine ; and alkylamine oxides such as lauryldimethylamine oxide.
Among these surfactants, polyglycerin saturated fatty acid esters described above as examples of nonionic surfactant of fatty acid ester type (d-2) are particularly preferred because of excellent stability at low temperatures of the aqueous suspension pesticide preparation.
Use of the water-soluble protein (f) in the aqueous suspension pesticide preparation makes it possible to impart excellent storage stability. Examples of the water-soluble protein (f) include milk protein, vegetable protein, animal protein, or protein preparations made of these proteins, for example, one or more kinds selected from skim milk, whole milk powder, lactoalbumin hydrolysate, casein, alkali metal salt of casein (e.g., sodium caseinate), whey protein, soybean powder, fish powder, gelatin, egg white powder, and egg yolk powder. Among these water-soluble proteins, sodium caseinate is particularly preferred.
The amount of the active pesticide ingredient (a) in the aqueous suspension pesticide preparation of the present invention is preferably within a range from 1 to 45% by weight, and is particularly preferably from 5 to 40% by weight. The amount of the compound (b) represented by the general formula (1) in the aqueous suspension pesticide preparation of the present invention is preferably within a range from 0.5 to 10% by weight, and is particularly preferably from 1 to 8% by weight. The amount of the hydrogenated phospholipid (c) having an iodine value of 20 or less in the aqueous suspension pesticide preparation of the present invention is preferably within a range from 0.5 to 10% by weight, and is particularly preferably from 1 to 8% by weight. The amount of the surfactant (d) having a C6 - C2o alkyl group in the aqueous suspension pesticide preparation of the present invention is preferably within a range from 0.5 to 10% by weight, and is particularly preferably from 1 to 8% by weight. The amount of water (e) in the aqueous suspension pesticide preparation of the present invention is preferably within a range 25 to 97.5% by weight, and is particularly preferably from 36 to 92% by weight. When using the water-soluble protein (f) in combination in the aqueous suspension pesticide preparation of the present invention, the total amount of the hydrogenated phospholipid and the water-soluble protein is preferably within a range from 0.5 to 10% by weight, and is particularly preferably from 1 to 8% by weight.
The mixing ratio of the active pesticide ingredient (a) to the compound (b) represented by the general formula (1) in the aqueous suspension pesticide preparation is preferably within a range from 0.1:1 to 90:1, and is particularly preferably from 0.6:1 to 40:1. The mixing ratio of the active pesticide ingredient (a) to the hydrogenated phospholipid (c) having an iodine value of 20 or less in the aqueous suspension pesticide preparation is preferably within a range from 0.1:1 to 90:1, and is particularly preferably from 0.6:1 to 40:1. The mixing ratio of the active pesticide ingredient (a) to the surfactant (d) having a C6 - C2o alkyl group in the aqueous suspension pesticide preparation is preferably within a range from 0.1:1 to 90:1, and is particularly preferably from 0.6:1 to 40:1.
In the case in which the water-soluble protein (f) is mixed with the aqueous suspension pesticide preparation, the mixing ratio of the active pesticide ingredient (a) to the total of the hydrogenated phospholipid (c) having an iodine value of 20 or less and the water-soluble protein (f) is preferably within a range from 0.1:1 to 90:1, and is particularly preferably from 0.6:1 to 40:1. The mixing ratio of the hydrogenated phospholipid (c) having an iodine value of 20 or less to the water-soluble protein (f) is preferably within a range from 1:0.1 to 1:10.
As long as the effects of the present invention are not impaired, the aqueous suspension pesticide preparation of the present invention may further contain other arbitrary ingredients, and examples of the other arbitrary ingredient include antifreeze agents, preservatives, and pH adjustors.
Examples of the antifreeze agent include water-soluble organic solvents such as ethylene glycol, propylene glycol or propylene glycol monomethyl ether; and urea. When using the antifreeze agent, the antifreeze agent is preferably used in place of water in an amount within a range from about 1/50 to 1/4 of the amount of water (e) in the aqueous suspension pesticide preparation.
In the preparation of the aqueous suspension pesticide preparation, it is necessary to sufficiently mix the respective ingredients. Although the surfactant (d) having a Cs - C2o alkyl group is usually added at one time, a portion thereof can be added to the active pesticide ingredient (a) , the compound (b) represented by the general formula (1) and the hydrogenated phospholipid (c) having an iodine value of 20 or less, and then the rest can be added to water (e) .
Although the mixing sequence is not specifically limited, it is preferable that the compound (b) represented by the general formula' (1) and the hydrogenated phospholipid (c) having an iodine value of 20 or less and, if necessary, the water-soluble protein (f) be mixed, and then the active pesticide ingredient (a) and the surfactant (d) having a Ce - C2o alkyl group be added, in order to easily prepare a homogeneous mixture.
In the case of mixing the active pesticide ingredient (a) , the compound (b) represented by the general formula (1), the hydrogenated phospholipid (c) having an iodine value of 20 or less and the surfactant (d) having a C6 - C2o alkyl group, it is not preferable that water (e) be simultaneously added and mixed. In the case of mixing the active pesticide ingredient (a) , the compound (b) represented by the general formula (1), the hydrogenated phospholipid (c) having an iodine value of 20 or less and the surfactant (d) having a C6 - C2o alkyl group, it is preferable that they be mixed by properly heating. In that case, since coloration occurs when treated at high temperature, the treatment temperature is preferably 80°C or lower, and is particularly preferably within a range from 50 to 70°C.
As the method of adding water to form a suspension, a conventionally known method can be used. Examples thereof include a method (1) of adding water to a previously prepared mixture of the active pesticide. ingredient (a) , the compound (b) represented by the general formula (1), the hydrogenated phospholipid (c) having an iodine value of 20 or less and the surfactant (d) having a C6 - C2o alkyl group and, if necessary, the water-soluble protein (f) and stirring with a homomixer, and a method (2) of adding a previously prepared mixture of the active pesticide ingredient (a) , the compound (b) represented by the general formula (1), the hydrogenated phospholipid (c) having an iodine value of 20 or less and the rest of the surfactant (d) and, if necessary, the water-soluble protein (f) in water into which a portion of the surfactant has been dissolved.
The aqueous suspension pesticide preparation of the present invention can be further formed into fine particles by a high speed homogenizer or a high pressure emulsifying machine .
It is believed that suspension particles in the obtained aqueous suspension pesticide preparation of the present invention, which has stable water dispersibility, are formed by surrounding the active pesticide ingredient (a) with the ingredients (b) to (d) .
The average particle size of suspension particles in the aqueous suspension pesticide preparation of the present invention as measured by a laser diffraction and scattering type particle size analyzer is preferably within a range from 0.1 to 20 μπι, and is particularly preferably from 0.5 to 7 pm. The lower limit of the average particle size of suspension particles in the aqueous suspension pesticide preparation is not limited because the average particle size of 0.1 pm or less cannot be measured by the laser diffraction and scattering type particle size analyzer and dispersed particles having an average particle size of 0.1 pm or less can be used without any obstacles.
The viscosity of the aqueous suspension pesticide preparation of the present invention is preferably within a range from 50 to 5000 mPa · s . The greater the amounts (with respect to water) of the compound (b) represented by the general formula (1), the hydrogenated phospholipid (c) having an iodine value of 20 or less, the surfactant (d) having a C6 - C2o alkyl group, and the water-soluble protein (f) , which is optionally added, the higher the viscosity tends to become. Therefore, the inhibition effects against sedimentation of suspension particles due to the increased viscosity, in addition to the stabilization of the suspension particles, affect the stability of the suspension more advantageously. However, the viscosity of the aqueous suspension pesticide preparation of the present invention is preferably within a range from 100 to 1000 mPa · s in view of handling during application and easy dilution with water.
EXAMPLES The following Examples and Comparative Examples further illustrate the present invention in detail; however, the present invention is not limited by these Examples. In the following Examples and Comparative Examples, parts and percentages are by weight unless otherwise specified.
Example 1 Parts of iminoctadine tris (albesilate) , 3.7 parts of lauryl alcohol, 2 parts of hydrogenated soybean lecithin (Basis™ LP-20H, manufactured by Nisshin Oil Mills, Ltd., iodine value: 7.7), 0.5 parts of sodium casein, 4 parts of hexaglycerin stearate and 5 parts of ethylene glycol were mixed and heated to 70 °C to yield a homogeneous mixture. To the obtained mixture maintained at 50 °C was slowly added water while stirring to yield 100 parts of a suspension. This suspension was stirred in a homomixer at 3,000 rpm for 10 minutes to obtain an aqueous suspension pesticide preparation. The average particle size of the resulting aqueous suspension pesticide preparation was measured by using a laser diffraction and scattering type particle size analyzer. As a result, the average particle size was 4.4 m. The viscosity was measured by using a B-type viscometer (30 rpm/20°C) . As a result, the viscosity was 170 mPa · s .
Example 2 Parts of iminoctadine tris (albesilate) , 3.7 parts of lauryl alcohol, 2 parts of hydrogenated soybean lecithin (Basis™ LP-20H, manufactured by Nisshin Oil Mills, Ltd., iodine value: 6.7), 0.5 parts of lactoalbumin hydrolysate (manufactured by Wako Pure Chemical Ind. , Ltd.), 2 parts of decaglycerin laurate, 2 parts of decaglycerin stearate and 5 parts of ethylene glycol were mixed and heated to 70 QC to yield a homogeneous mixture. To the obtained mixture maintained at 50°C was slowly added water while stirring to yield 100 parts of a suspension. This suspension was stirred in a homomixer at 3,000 rpm for 10 minutes to obtain an aqueous suspension pesticide preparation.
In the same manner as in Example 1, the average particle size and the viscosity were measured. As a result, the average particle size was 5.2 μκι and the viscosity was 780 mPa · s .
Example 3 Parts of iminoctadine tris (albesilate) , 4 parts of lauryl alcohol, 2 parts of hydrogenated soybean lecithin (Basis™ LP-20H, manufactured by Nisshin Oil Mills, Ltd., iodine value: 7.7), 4 parts, of decaglycerine laurate and 5 parts of ethylene glycol were mixed and heated to 70 °C to yield a homogeneous mixture. To the obtained mixture maintained at 50°C was slowly added water while stirring to yield 100 parts of a suspension. This suspension was stirred in a homomixer at 3,000 rpm for 10 minutes to obtain an aqueous suspension pesticide preparation.
In the same manner as in Example 1, the average particle size and the viscosity were measured. As a result, the average particle size was 4.3 μπι and the viscosity was 190 mPa · s .
Example 4 Parts of iminoctadine tris (albesilate ) , 5 parts of dietylene glycol mono-2-ethyl hexyl ether, 2 parts of hydrogenated soybean lecithin (Basis™ LP-20H, manufactured by Nisshin Oil Mills, Ltd., iodine value: 7.7), 0.5 parts of sodium casein, 4 parts of hexaglycerin stearate and 5 parts of ethylene glycol were mixed and heated to 70 °C to yield a homogeneous mixture. To the obtained mixture maintained at 50 °C was slowly added water while stirring to yield 100 parts of a suspension. This suspension was stirred in a homomixer at 3,000 rpm for 10 minutes to obtain an aqueous suspension pesticide preparation.
In the same manner as in Example 1, the average particle size and the viscosity were measured. As a result, the average particle size was 3.5 um and the viscosity was 280 mPa · s .
Comparative Example 1 Parts of iminoctadine tris (albesilate) , 2 parts of lauryl alcohol, 2 parts of soybean lecithin (Basis™ LP-20, manufactured by Nisshin Oil Mills, Ltd., iodine value: 80), 2 parts of decaglycerol laurate, 2 parts of decaglycerin laurate , 1.5 parts of decaglycerin oleate and 5 parts of ethylene glycol were mixed and heated to 70°C to yield a homogeneous mixture. To the obtained mixture maintained at 50°C was slowly added water while stirring to yield 100 parts of a suspension. This suspension was stirred in a homomixer at 10,000 rpm for 10 minutes to obtain an aqueous suspension pesticide preparation.
In the same manner as in Example 1, the average particle size and the viscosity were measured. As a result, the average particle size was 3.2 um and the viscosity was 480 mPa · s .
Comparative Example 2 Parts of iminoctadine tris (albesilate) , 4 parts of lauryl alcohol, 2 parts of soybean lecithin (Basis™ LP-20, manufactured by Nisshin Oil Mills, Ltd., iodine value: 80), 4 parts of decaglycerin laurate and 5 parts of ethylene glycol were mixed and heated to 70°C to yield a homogeneous mixture. To the obtained mixture maintained at 50 °C was slowly added water while stirring to yield 100 parts of a suspension. This suspension was stirred in a homomixer at 10,000 rpm for 10 minutes to obtain an aqueous suspension pesticide preparation. In the same manner as in Example 1, the average particle size and the viscosity were measured. As a result, the average particle size was 4.4 μπι and the viscosity was 250 mPa · s .
Comparative Example 3 Parts of iminoctadine tris (albesilate) , 4 parts of lauryl alcohol, 2 parts of egg yolk lecithin (manufactured by Wako Pure Chemical Ind., Ltd., iodine value: 60), 4 parts of decaglycerin laurate and 5 parts of ethylene glycol were mixed and heated to 70 °C to yield a homogeneous mixture. To the obtained mixture maintained at 50°C was slowly added water while stirring to yield 100 parts of a suspension. This suspension was stirred in a homomixer at 10,000 rpm for 10 minutes to obtain an aqueous suspension pesticide preparation.
In the same manner as in Example 1, the average particle size and the viscosity were measured. As a result, the average particle size was 5.2 μπι and the viscosity was 340 mPa · s .
Comparative Example 4 Parts of iminoctadine tris (albesilate) , 5 parts of dipropylene glycol monobutyl ether, 2 parts of soybean lecithin (Basis™ LP-20, manufactured by Nisshin Oil Mills, Ltd., iodine value: 80), 4 parts of decaglycerin laurate and 5 parts of ethylene glycol were mixed and heated to 70°C to yield a homogeneous mixture. To the obtained mixture maintained at 50 °C was slowly added water while stirring to yield 100 parts of a suspension. This suspension was stirred in a homomixer at 3,000 rpm for 10 minutes to obtain an aqueous suspension pesticide preparation.
Immediately after preparation of the obtained aqueous suspension pesticide preparation, an average particle size and a viscosity were measured in the same manner as in Example 1. As a result, the average particle size was 10.8 μπι and the viscosity was 1090 mPa · s . However, after standing at 40°C for 3 days, an yellow viscous substance sedimented and was isolated. Therefore, the stable suspension state broke.
(Test Example 1) Storage test at high temperature conditions Each aqueous suspension pesticide preparation thus prepared was charged in a 500 ml glass bottle and was then allowed to stand in a temperature-controlled chamber at 50 °C for 12 weeks. Various tests were carried out. The results are shown in Table 1. After the completion of the storage, the suspension state of each sample was observed. After the sample was allowed to stand at 20°C for 24 hours, recovery of the suspension state was examined.
The test results are evaluated according to the following criteria . @: suspension state is very good and active pesticide ingredient is satisfactorily dispersed O: suspension state is very good and active pesticide ingredient is satisfactorily dispersed and, although slight water separation is observed in the upper layer, homogeneous suspension is easily achieved by shaking by hand Δ: suspension state is slightly poor and, although a portion of the suspension is deposited on the wall of the container, suspension is achieved by stirring with a stick χ ; suspension state is poor and nearly the entire suspension is in the form of a gel, while a portion thereof agglomerates but is not easily dispersed by stirring with a stick Samples, after standing for 12 weeks, were allowed to stand at 20°C for 24 hours and, after 500-fold dilution, it was determined by an optical microscope whether or hot cryst precipitates could be observed in the diluted solution.
Measurement of residue on sieve> Each sample, after standing for 12 weeks, was allowed to stand at 20°C for 24 hours, and 50 g of each sample was diluted with 1 L of water. The total amount of the resulting diluted solution was passed through a sieve having holes of 45 urn. Then, 1 L of water was poured onto the sieve, and the sieve was moved horizontally. This operation of washing with water was repeated five times. After washing with water, the amount of the residue on the sieve was measured and the crystal precipitation % was calculated by the following equation: Crystal precipitation (% by weight) = - . !^ !1?/0! ^????- ^ r~r x 100 ' r r (Amount of (a) + (b) + (c) + (d) + (f) in 50—; g of sample) where (a) denotes the weight of the active pesticide ingredient, (b) denotes the weight of a compound represented by the general formula (1), (c) denotes the weight of a hydrogenated phospholipid having an iodine value of 20 or less, (d) denotes the weight of a surfactant having a C6 to C2o alkyl group, and (f) denotes the weight of a water-soluble protein.
Table 1 (Test Example 2) Storage test under high temperature/low temperature cycle conditions Each aqueous suspension pesticide preparation thus prepared was charged in a 500 ml glass bottle, allowed to stand at a set temperature of 50°C for 3 days, cooled to -10°C from 50 °C over 12 hours, allowed to stand at a set temperature of -10°C for 3 days and heated to 50°C from -10°C over 12 hours (one cycle per week) , and then this cycle was repeated 12 times (12 weeks) and each sample was stored. In the same manner as in Test Example 1, the storage stability test, observation of presence or absence of crystal precipitates and measurement of residue on the sieve were carried out. The results are shown in Table 2.
After the completion of the storage test, the aqueous suspension pesticide preparation prepared in Comparative Example 3 was slightly deposited on the wall of the container at the upper portion of the liquid level in the form of a ring-shaped solid. After recovery at 20°C, water separation was observed in the upper layer. The amount of the residue on the sieve was 1% by weight.
Table 2 (Test Example 3) Storage test under conditions at low temperature Each aqueous suspension pesticide preparation thus prepared was charged in a 500 ml glass bottle and was then allowed to stand at a set temperature of -5°C for 12 weeks.
In the same manner as in Test Example 1, the storage stability test, observation of presence or absence of crystal precipitates and measurement of residue on the sieve were carried out. The results are shown in Table 3. The aqueous suspension pesticide preparation prepared in Example 3 was in a creamy solidified state after the completion of the storage test and, after recovery at 20 °C, it reverted to a suspension. In contrast, the aqueous suspension pesticide preparation prepared in Comparative Example 1 was partially in the viscous state after the completion of the storage test and, even after recovery at 20 °C, water separation was observed in the upper layer and clogging was caused by the residue on the sieve. The amount of the residue on the sieve was 2% by weight.
The aqueous suspension pesticide preparation prepared in Comparative Example 2 was in a creamy solidified state after the completion of the storage test and, even after recovery at 20°C, water separation was observed in the upper layer and clogging was caused by the residue on the sieve. The amount of the residue on the sieve was 2% by weight.
The aqueous suspension pesticide preparation prepared in Comparative Example 3 was in a creamy solidified state after the completion of the storage test and, even after recovery at °C, water separation was observed in the upper layer and clogging was caused by the residue on the sieve. The amount of the residue on the sieve was 3% by weight.
Table 3 creamy solidified state (Test Example 4) Storage test under low temperature cycle conditions Each aqueous suspension pesticide preparation thus prepared was charged in a 500 ml glass bottle, was allowed to stand at a set temperature of 5°C for 6 hours, was cooled to -10°C from 5°C over 6 hours, was allowed to stand at a set temperature of -10°C for 6 hours, and was heated to 5°C from -10°C over 6 hours (one cycle) , and then this cycle was repeated 84 times (12 weeks) and each sample was stored. In the same manner as in Test Example 1, the storage stability test, observation of presence or absence of crystal precipitates and measurement of residue on the sieve were carried out. The results are shown in Table 4.
After the completion of the storage test, the aqueous suspension pesticide preparation prepared in Comparative Example 3 was in a creamy solidified state. After recovery at 20°C, it reverted to a good suspension. In contrast, the aqueous suspension pesticide preparations prepared in Comparative Examples 1, 2 and 3 were in a creamy solidified state after the completion of the storage test and, even after recovery at 20 °C, they did not revert to a good suspension. Therefore, clogging was caused by the residue on the sieve. Since it is difficult to pass the residue through the sieve at one time by one operation, filtration was carried out in three portions. The amount of the residue on the sieve was 12% by weight in Comparative Example 1, 9% by weight in Comparative Example 2, or 18% by weight in Comparative Example 3.
Table 4 creamy solidified state INDUSTRIAL APPLICABILITY The aqueous suspension pesticide preparation of the present invention not only has excellent storage stability under storage conditions where the temperature changes drastically in a long cycle through the seasons, but also excellent storage stability under storage conditions where the temperature changes within a range from 5 to -10 °C in a short cycle through day and night.
Claims (6)
1. An aqueous suspension pesticide preparation which includes (a) a 1, 1' -iminiodi (octamethylene) diguanidinium tris (alkyl-benzenesulfonate) ; (b) a compound represented by the general formula (1) : R-0- (CH2CH20)n-H (wherein R represents a Cs - Ci8 alkyl group and n represents an integer of 0 to 4); (c) a phospholipid; (d) a surfactant having a C6 - C20 alkyl group; and (e) water; wherein the phospholipid (c) is a hydrogenated phospholipid having an iodine value of 20 or less.
2. A pesticide preparation as claimed in claim 1, which further contains (f) a water-soluble protein.
3. An aqueous suspension pesticide preparation according to claim 1, wherein the alkyl-benzenesulfonate constituting the 1,1' -iminiodi (octamethylene) diguanidinium tris (alkyl-benzenesulfonate) (a) is benzene sulfonate having a Ci0 - Ci3 alkyl group and the compound (b) represented by the general formula (1) is a compound having a Ci0 - C13 alkyl group.
4. An aqueous suspension pesticide preparation according to claim 3, wherein the surfactant (d) is a surfactant having a Cio - Ci3 alkyl group.
5. An aqueous suspension pesticide preparation according to claim 1, wherein each of the alkyl group of the alkyl-benzenesulfonate constituting the 1,1'-iminiodi (octamethylene) diguanidinium tris (alkyl-benzenesulfonate) , the alkyl group of the compound represented by the general formula (1) , and the alkyl group constituting the surfactant is an alkyl group having the same number of carbon atoms.
6. An aqueous suspension pesticide preparation according to claim 1, wherein an average particle size of suspension particles in the aqueous suspension pesticide preparation as measured by a laser diffraction and scattering method of measuring the particle size is 20 μπι or less. For the Applicant WOLFF, BREGMAN AND GOLLER
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000330431 | 2000-10-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL146103A0 IL146103A0 (en) | 2002-07-25 |
| IL146103A true IL146103A (en) | 2006-10-31 |
Family
ID=18806954
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL146103A IL146103A (en) | 2000-10-30 | 2001-10-22 | Aqueous pesticide containing a diguanidinium alkybenzenesulfonate derivative |
Country Status (6)
| Country | Link |
|---|---|
| KR (1) | KR100764044B1 (en) |
| CN (1) | CN1212770C (en) |
| AU (1) | AU779666B2 (en) |
| BR (1) | BR0104887A (en) |
| IL (1) | IL146103A (en) |
| TW (1) | TWI241162B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2704566A1 (en) * | 2011-05-02 | 2014-03-12 | Basf Se | A method for enhancing the performance of a pesticide with guanidines |
| TWI789026B (en) | 2020-09-24 | 2023-01-01 | 南韓商Ｌｇ化學股份有限公司 | Water-soluble composition comprising lysophosphatidylethanolamine and having improved stability, and method for preparing the same |
| AU2021366966A1 (en) * | 2020-10-19 | 2023-03-02 | Oxiteno S.A. Indústria E Comércio | Composition, agrochemical formulation, methods for increasing water and nutrient availability and for improving pest control in plants and seeds, and uses of the composition and the agrochemical formulation |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5437825A (en) * | 1977-08-30 | 1979-03-20 | Kureha Chem Ind Co Ltd | Controlling agents for spray in a small amount effective against blast and injurious insects in the paddy field at the same time. |
| JPS63290803A (en) * | 1987-05-22 | 1988-11-28 | Sumitomo Chem Co Ltd | Stable solid agricultural chemical formulation |
| JPH02279607A (en) * | 1989-04-18 | 1990-11-15 | Dainippon Ink & Chem Inc | Aqueous suspension-like biocidal composition |
| FR2670085B1 (en) * | 1990-12-10 | 1996-12-13 | Rhone Poulenc Chimie | PHYTOSANITARY SUSPENSIONS. |
| JP3233251B2 (en) * | 1995-02-23 | 2001-11-26 | 大日本インキ化学工業株式会社 | Aqueous suspension type pesticide formulation |
-
2001
- 2001-10-15 AU AU79420/01A patent/AU779666B2/en not_active Expired
- 2001-10-22 IL IL146103A patent/IL146103A/en active IP Right Grant
- 2001-10-24 TW TW090126254A patent/TWI241162B/en not_active IP Right Cessation
- 2001-10-29 KR KR1020010066719A patent/KR100764044B1/en not_active Expired - Lifetime
- 2001-10-30 CN CNB011375795A patent/CN1212770C/en not_active Expired - Lifetime
- 2001-10-30 BR BR0104887-2A patent/BR0104887A/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| KR20020033542A (en) | 2002-05-07 |
| IL146103A0 (en) | 2002-07-25 |
| AU779666B2 (en) | 2005-02-03 |
| TWI241162B (en) | 2005-10-11 |
| CN1212770C (en) | 2005-08-03 |
| KR100764044B1 (en) | 2007-10-09 |
| CN1350788A (en) | 2002-05-29 |
| AU7942001A (en) | 2002-05-02 |
| BR0104887A (en) | 2002-09-10 |
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