CN115088711A - Spreading agent for water-surface floating type pesticide composition and pesticide composition containing same - Google Patents
Spreading agent for water-surface floating type pesticide composition and pesticide composition containing same Download PDFInfo
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- CN115088711A CN115088711A CN202210564540.7A CN202210564540A CN115088711A CN 115088711 A CN115088711 A CN 115088711A CN 202210564540 A CN202210564540 A CN 202210564540A CN 115088711 A CN115088711 A CN 115088711A
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- agricultural chemical
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- 239000000203 mixture Substances 0.000 title claims abstract description 93
- 239000000575 pesticide Substances 0.000 title claims abstract description 27
- 238000003892 spreading Methods 0.000 title abstract description 49
- 239000003795 chemical substances by application Substances 0.000 title abstract description 34
- 150000001875 compounds Chemical class 0.000 claims abstract description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 39
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 33
- 239000004480 active ingredient Substances 0.000 claims abstract description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 32
- 230000000361 pesticidal effect Effects 0.000 claims abstract description 23
- 239000003905 agrochemical Substances 0.000 claims description 68
- 239000004606 Fillers/Extenders Substances 0.000 claims description 13
- 230000015572 biosynthetic process Effects 0.000 description 65
- 238000003786 synthesis reaction Methods 0.000 description 65
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 38
- -1 acetylene alcohols Chemical class 0.000 description 34
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 27
- 239000000843 powder Substances 0.000 description 25
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 18
- 239000003054 catalyst Substances 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 150000002009 diols Chemical class 0.000 description 10
- 239000008187 granular material Substances 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 125000006353 oxyethylene group Chemical group 0.000 description 9
- 238000012644 addition polymerization Methods 0.000 description 8
- 238000011156 evaluation Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000002994 raw material Substances 0.000 description 8
- 230000032683 aging Effects 0.000 description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- DWANEFRJKWXRSG-UHFFFAOYSA-N 1,2-tetradecanediol Chemical compound CCCCCCCCCCCCC(O)CO DWANEFRJKWXRSG-UHFFFAOYSA-N 0.000 description 4
- CHAMQQHQVVMXDS-UHFFFAOYSA-N 2-ethyl-4-methylhexane-1,3-diol Chemical compound CCC(C)C(O)C(CC)CO CHAMQQHQVVMXDS-UHFFFAOYSA-N 0.000 description 4
- SDQROPCSKIYYAV-UHFFFAOYSA-N 2-methyloctane-1,8-diol Chemical compound OCC(C)CCCCCCO SDQROPCSKIYYAV-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- HFEJHAAIJZXXRE-UHFFFAOYSA-N cafenstrole Chemical compound CCN(CC)C(=O)N1C=NC(S(=O)(=O)C=2C(=CC(C)=CC=2C)C)=N1 HFEJHAAIJZXXRE-UHFFFAOYSA-N 0.000 description 4
- 239000004927 clay Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 150000007514 bases Chemical class 0.000 description 3
- 239000000440 bentonite Substances 0.000 description 3
- 229910000278 bentonite Inorganic materials 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000007799 cork Substances 0.000 description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 238000001125 extrusion Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 230000001788 irregular Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 125000005702 oxyalkylene group Chemical group 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 239000004576 sand Substances 0.000 description 3
- RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 239000005662 Paraffin oil Substances 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- YLPGTOIOYRQOHV-UHFFFAOYSA-N Pretilachlor Chemical compound CCCOCCN(C(=O)CCl)C1=C(CC)C=CC=C1CC YLPGTOIOYRQOHV-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- XMQFTWRPUQYINF-UHFFFAOYSA-N bensulfuron-methyl Chemical group COC(=O)C1=CC=CC=C1CS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 XMQFTWRPUQYINF-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910052570 clay Inorganic materials 0.000 description 2
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 description 2
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- GHLKSLMMWAKNBM-UHFFFAOYSA-N dodecane-1,12-diol Chemical compound OCCCCCCCCCCCCO GHLKSLMMWAKNBM-UHFFFAOYSA-N 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 150000002484 inorganic compounds Chemical class 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- 239000004005 microsphere Substances 0.000 description 2
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- KOFLVDBWRHFSAB-UHFFFAOYSA-N 1,2,4,5-tetrahydro-1-(phenylmethyl)-5,9b(1',2')-benzeno-9bh-benz(g)indol-3(3ah)-one Chemical compound C1C(C=2C3=CC=CC=2)C2=CC=CC=C2C23C1C(=O)CN2CC1=CC=CC=C1 KOFLVDBWRHFSAB-UHFFFAOYSA-N 0.000 description 1
- BTOOAFQCTJZDRC-UHFFFAOYSA-N 1,2-hexadecanediol Chemical compound CCCCCCCCCCCCCCC(O)CO BTOOAFQCTJZDRC-UHFFFAOYSA-N 0.000 description 1
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 239000005472 Bensulfuron methyl Substances 0.000 description 1
- NNYRZQHKCHEXSD-UHFFFAOYSA-N Daimuron Chemical compound C1=CC(C)=CC=C1NC(=O)NC(C)(C)C1=CC=CC=C1 NNYRZQHKCHEXSD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004373 Pullulan Substances 0.000 description 1
- 229920001218 Pullulan Polymers 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- INSRQEMEVAMETL-UHFFFAOYSA-N decane-1,1-diol Chemical compound CCCCCCCCCC(O)O INSRQEMEVAMETL-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- GTZOYNFRVVHLDZ-UHFFFAOYSA-N dodecane-1,1-diol Chemical compound CCCCCCCCCCCC(O)O GTZOYNFRVVHLDZ-UHFFFAOYSA-N 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 238000005188 flotation Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- MHIBEGOZTWERHF-UHFFFAOYSA-N heptane-1,1-diol Chemical compound CCCCCCC(O)O MHIBEGOZTWERHF-UHFFFAOYSA-N 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000000411 inducer Substances 0.000 description 1
- 239000000077 insect repellent Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- FVXBCDWMKCEPCL-UHFFFAOYSA-N nonane-1,1-diol Chemical compound CCCCCCCCC(O)O FVXBCDWMKCEPCL-UHFFFAOYSA-N 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000010451 perlite Substances 0.000 description 1
- 235000019362 perlite Nutrition 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000019423 pullulan Nutrition 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- CQTBQILMJBCTRS-UHFFFAOYSA-N tetradecane-1,1-diol Chemical compound CCCCCCCCCCCCCC(O)O CQTBQILMJBCTRS-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- ZUDWINGCBFUXNG-UHFFFAOYSA-N tridecane-1,1-diol Chemical compound CCCCCCCCCCCCC(O)O ZUDWINGCBFUXNG-UHFFFAOYSA-N 0.000 description 1
- GRXOWOKLKIZFNP-UHFFFAOYSA-N undecane-1,1-diol Chemical compound CCCCCCCCCCC(O)O GRXOWOKLKIZFNP-UHFFFAOYSA-N 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
Images
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
-
- 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
- A01N25/12—Powders or granules
- A01N25/14—Powders or granules wettable
Landscapes
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The present invention relates to a spreading agent for a water-surface floating type pesticidal composition and a pesticidal composition comprising the same. An object of the present invention is to provide: a spreading agent for a water-surface floating pesticide composition, which can give a granular pesticide composition prepared by using a pesticide active ingredient in combination with the pesticide active ingredient and which has excellent spreading properties when applied to water and can disintegrate the whole composition on the water surface. The spreading agent for the water-surface floating type pesticide composition of the invention contains HO-R 1 ‑O‑G 1 A compound represented by the formula (wherein R is 1 Is an alkylene group having 6 to 14 carbon atoms, G 1 Is- (R) 5 O) s -a group having a valence of 2 as indicated,R 5 is an alkylene group having 2 or 3 carbon atoms, s is an integer of 1 to 10, and s is 2 or more, - (R) 5 O) s R in (A-C) 5 Optionally all the same or different. ).
Description
The present application is a divisional application of chinese patent application entitled "a spreading agent for a water surface floating type agricultural chemical composition and an agricultural chemical composition comprising the same" on the application date of 2021, 5/17/2021, application number of 202110534005.2.
Technical Field
The present invention relates to: a granular pesticidal composition to be applied to a water surface of agricultural land and a spreading agent for a water-surface floating pesticidal composition, which contains a pesticidal active ingredient (pesticidal active ingredient) together with the pesticidal active ingredient, and spreads the pesticidal active ingredient sufficiently on the water surface.
Background
For example, in order to obtain a sufficient effect of an agricultural chemical sprayed on a paddy field, that is, in order to disperse the sprayed agricultural chemical over the entire paddy field without localized presence, an agricultural chemical (agricultural chemical composition) having a granular form using an agricultural chemical active ingredient in combination with a spreading agent is widely used. The spreading agent is required to have long spreading distance and high spreading speed after being contacted with water.
Patent document 2 discloses a spreading agent for a water-surface floating type agricultural chemical composition, which comprises: selected from (RCOO) m X(OH) n (R is an aliphatic hydrocarbon group having 6 to 9 carbon atoms, X is a residue obtained by removing all hydroxyl groups from a 1 to 4-valent aliphatic hydroxyl compound having 2 to 8 carbon atoms, m is an integer of 1 to 3, n is 0 or an integer of 1 to 3, and an integer satisfying 1. ltoreq. m + n. ltoreq.4) and at least one or more of phosphate ester salts and sulfate ester salts thereof.
Patent document 4 discloses a water-surface-floating pesticide granular composition containing: a pesticide active ingredient; HO- (A) 1 -O) m -X 1 -(O-A 2 ) n -OH(X 1 A saturated hydrocarbon group having 6 to 14 carbon atoms and a valence of 2 1 And A 2 Each represents an alkylene group having 2 to 4 carbon atoms, and m and n each represent an integer. m and n are any one of integers of 1 to 7 in total, and when m is an integer of 2 or more, each A 1 The same or different, each A is an integer of 2 or more 2 The same or different) are selected from the group consisting of chain diol derivatives; condensed phosphoric acid or a salt thereof; and, a flotation aid and an extender.
Patent document 5 discloses a spreading agent for a water-floating agricultural chemical composition, which is characterized by comprising: r 1 COO-(AO) n -R 2 (R 1 : a C6-9 linear alkyl group or a C6-9 branched alkyl group, AO: oxyalkylene group having 2 carbon atoms, n: an integer of 3 to 4, R 2 : a C1-2 linear alkyl group. ) Ester compounds are shown.
Documents of the prior art
Patent document
Patent document 1: japanese laid-open patent publication No. 6-336403
Patent document 2: japanese patent laid-open publication No. 2003-238307
Patent document 3: japanese patent laid-open No. 2007-39344
Patent document 4: japanese patent laid-open publication No. 2009-114102
Patent document 5: japanese patent laid-open publication No. 2018-100261
Disclosure of Invention
Problems to be solved by the invention
An object of the present invention is to provide: a spreading agent for a water-floating agricultural chemical composition, which contains an agricultural chemical active ingredient together with the agricultural chemical active ingredient, for example, is suitable for providing a granular agricultural chemical composition and is used as an additive capable of sufficiently spreading the agricultural chemical active ingredient on the water surface of agricultural land. Another object of the present invention is to provide: a water-floating agricultural chemical composition which is applied to the water surface of agricultural land and has excellent spreadability of an agricultural chemical active ingredient on the water surface after application.
Means for solving the problems
The inventors of the present invention conducted extensive studies and found that: when a granular product prepared by using a combination of an agricultural chemical active ingredient and a specific diol compound is sprayed on water, the agricultural chemical active ingredient spreads sufficiently.
The present invention is as follows.
The spreading agent for a water-floating agricultural chemical composition of the present invention is characterized by containing a compound represented by the following general formula (1).
HO-R 1 -O-G 1 -H (1)
(in the formula, R 1 Is an alkylene group having 6 to 14 carbon atoms, G 1 Is- (R) 5 O) s -a group having a valence of 2, R 5 Is an alkylene group having 2 or 3 carbon atoms, s is an integer of 1 to 10, and s is 2 or more, - (R) 5 O) s R in (A-C) 5 Optionally all the same or different. )
The spreading agent for a water-floating agricultural chemical composition of the present invention may further contain a compound represented by the following general formula (2).
H-G 2 -O-R 2 -O-G 3 -H (2)
(in the formula, R 2 Is C6-14 alkylene, G 2 Is- (OR) 7 ) t -a group having a valence of 2, R 7 Is an alkylene group having 2 OR 3 carbon atoms, t is an integer of 1 to 10, and when t is 2 OR more, - (OR) 7 ) t R in (a-C) 7 Optionally all of the same or different, G 3 Is- (R) 9 O) u -a group having a valence of 2, R 9 Is a carbon atomAn alkylene group having a number of 2 or 3, u is an integer of 1 to 10, and u is 2 or more, - (R) 9 O) u R in (A-C) 9 Optionally all the same or different. )
The water-surface floating type agricultural chemical composition of the present invention is characterized by containing: an agricultural chemical active ingredient, and the above-mentioned spreader for a water-surface floating agricultural chemical composition of the present invention.
The water-surface floating type pesticidal composition of the present invention may further contain an extender.
ADVANTAGEOUS EFFECTS OF INVENTION
According to the present invention, if a granulated product (water-surface floating agricultural chemical composition) prepared by using a combination of a spreading agent for a water-surface floating agricultural chemical composition and an agricultural chemical active ingredient is sprayed on water, an effect of spreading the agricultural chemical active ingredient sufficiently can be obtained. Therefore, the water-surface floating type pesticidal composition of the present invention is useful for application to agricultural land having a water surface. In addition, the spreading agent for a water-surface-floating pesticide composition of the present invention is excellent in the granulation property of the pesticide active ingredient, and therefore, the granular water-floating pesticide composition can be easily applied to water surfaces.
Drawings
FIG. 1 is a schematic view of a container used for evaluating the spreadability of a pesticide composition in [ example ].
FIG. 2 is a schematic diagram illustrating the evaluation of the spreadability of the pesticide composition in [ example ].
Fig. 3 is a schematic view illustrating how the agricultural chemical composition is put on the water surface in evaluating the spreadability of the agricultural chemical composition in [ example ].
Detailed Description
The spreading agent for a water-surface floating agricultural chemical composition of the present invention contains a compound represented by the following general formula (1) (hereinafter, referred to as "diol compound (a)").
HO-R 1 -O-G 1 -H (1)
(in the formula, R 1 Is C6-14 alkylene, G 1 Is- (R) 5 O) s -a group having a valence of 2, R 5 Is of carbon number 2 or 3Alkylene, s is an integer of 1 to 10, and s is 2 or more, - (R) 5 O) s R in (A-C) 5 Optionally all the same or different. )
In the above general formula (1), the alkylene group R 1 The structure of (b) is not particularly limited, and may be linear or branched. R 1 The alkylene group in (1) has 6 to 14 carbon atoms, preferably 8 to 12 carbon atoms, and more preferably 8 to 9 carbon atoms. Alkylene radical R from the viewpoint of surface spreadability 1 Preferably a branched alkylene group having 8 to 12 carbon atoms. Preferred R 1 Specific examples of (3) are as follows.
In the above general formula (1), G is the structure 1 Alkylene of (A) to (B) 5 Is an alkylene group having 2 or 3 carbon atoms, that is, an ethylene group or a linear or branched propylene group. Thus, G 1 Containing oxyethylene (-C) 2 H 4 O-) or oxypropylene (-C) 3 H 6 O-)。
In the diol compound (A), s, which is the total number of oxyethylene groups or oxypropylene groups, is 1 to 10, preferably 2 to 8, and more preferably 3 to 8. When s is 2 or more, - (R) 5 O) S R in (A-C) 5 When both oxyethylene groups and oxypropylene groups are contained, these groups may be bonded to each other regularly or irregularly.
The diol compound (a) contained in the spreading agent for a water-surface floating type agricultural chemical composition of the present invention may be 1 kind or 2 or more kinds.
The method for producing the diol compound (a) is not particularly limited. A preferred production method is a method including the following steps (hereinafter referred to as "reaction steps"): reacting a C6-14 chain diol with at least one selected from the group consisting of ethylene oxide and propylene oxide in the presence of a catalyst. The following describes the production method.
Examples of the chain diol include straight chain alkanediols such as hexanediol, heptanediol, octanediol, nonanediol, decanediol, undecanediol, dodecanediol, tridecanediol, and tetradecanediol; branched alkanediols such as 2-butyl-2-ethyl-1, 3-propanediol, 2, 4-diethyl-1, 3-pentanediol and 2-methyl-1, 8-octanediol. The chain diol used in the reaction step may be only 1 kind or 2 or more kinds.
In the reaction step, a catalyst is used. The catalyst is not particularly limited, and a basic compound is preferred in terms of efficiently obtaining a desired product. The basic compound may be either an inorganic compound or an organic compound, and examples of the inorganic compound include potassium hydroxide, sodium hydroxide, lithium hydroxide, potassium carbonate, sodium carbonate, lithium carbonate, and the like. Examples of the organic compound include CH 3 ONa、C 2 H 5 ONa、CH 3 OLi、C 2 H 5 OLi、CH 3 OK、C 2 H 5 OK, etc. The amount of the catalyst to be used is preferably 0.1 to 10 millimolar equivalents based on 1 mole of the chain diol.
The above reaction step is carried out as follows: in a pressure reactor such as an autoclave, the temperature of the reaction system is preferably 100 to 170 ℃, more preferably 130 to 150 ℃, and the raw materials are stirred and pushed. To form a diol compound having a desired structure, ethylene oxide or propylene oxide may be added while changing the order, ratio, etc.
The above production method may further include a purification step, if necessary, after the reaction step. The purification step may include conventionally known operations such as chromatographic separation and concentration, which are carried out in the synthesis of general organic compounds.
The spreading agent for a water-surface floating type agricultural chemical composition of the present invention may further contain a compound represented by the following general formula (2) (hereinafter, referred to as "diol compound (B)") in order to improve the spreading property.
H-G 2 -O-R 2 -O-G 3 -H (2)
(in the formula, R 2 Is an alkylene group having 6 to 14 carbon atoms, G 2 Is- (OR) 7 ) t -a group having a valence of 2, R 7 Is an alkylene group having 2 OR 3 carbon atoms, t is an integer of 1 to 10, and when t is 2 OR more, - (OR) 7 ) t R in (A-C) 7 Optionally all of the same or different, G 3 Is- (R) 9 O) u -a group having a valence of 2, R 9 Is an alkylene group having 2 or 3 carbon atoms, u is an integer of 1 to 10, and u is 2 or more, - (R) 9 O) u R in (A-C) 9 Optionally all the same or different. )
In the above general formula (2), the alkylene group R 2 The structure of (b) is not particularly limited, and may be linear or branched. R is 2 The alkylene group in (1) has 6 to 14 carbon atoms, preferably 8 to 12 carbon atoms. Alkylene radical R from the viewpoint of surface spreadability 2 A branched alkylene group having 8 to 12 carbon atoms is preferred. Preferred R 2 Specific examples of (3) are as follows.
In the above general formula (2), G is the structure 2 Alkylene of (A) to (B) 7 Is an alkylene group having 2 or 3 carbon atoms, that is, an ethylene group or a linear or branched propylene group. Thus, G 2 Containing oxyethylene groups (-OC) 2 H 4 -) or oxypropylene (-OC) 3 H 6 -)。
In the diol compound (B), t, which is the total number of oxyethylene groups or oxypropylene groups, is 1 to 10, preferably 2 to 6, and more preferably 3 to 5. When t is 2 OR more, - (OR) 7 ) t R in (A-C) 7 When both oxyethylene groups and oxypropylene groups are contained, these groups may be bonded regularly or irregularly.
In the above general formula (2), G is the structure 3 Alkylene of (A) to (B) 9 The alkylene group having 2 or 3 carbon atoms is an ethylene group or a linear or branched propylene group. Thus, G 3 Containing oxyethylene (-C) 2 H 4 O-) or oxypropylene (-C) 3 H 6 O-)。
In the diol compound (B), u, which is the total number of oxyethylene groups or oxypropylene groups, is 1 to 10, preferably 2 to 6, and more preferably 3 to 5. When u is 2 or more, - (R) 9 O) u R in (A-C) 9 When both oxyethylene and oxypropylene groups are contained, which may be the same or different, these groups are regularly or irregularly linked and bonded.
The method for producing the diol compound (B) is not particularly limited. A preferred production method is a production method including the steps of: reacting a C6-14 chain diol with at least one selected from the group consisting of ethylene oxide and propylene oxide in the presence of a catalyst comprising a basic compound. In this case, the amount of the catalyst to be used is preferably 10 to 100 mmol equivalent, more preferably 15 to 50 mmol equivalent, based on 1 mol of the chain diol.
When the above diol compound (B) is contained in the spreading agent for a water-floating agricultural chemical composition of the present invention, the content ratio of the diol compound (a) to the diol compound (B) is preferably 40 to 99% by mass and 1 to 60% by mass, more preferably 60 to 98% by mass and 2 to 40% by mass, and still more preferably 80 to 98% by mass and 2 to 20% by mass, respectively, when the total of these components is 100% by mass.
The spreading agent for a water-surface floating type agricultural chemical composition of the present invention may further contain other components such as a binder, a disintegration accelerator, a dispersant, an emulsifier, a liquid medium (water, glycol, paraffin oil, etc.), a stabilizer, and the like, as required.
The spreading agent for a water-surface-floating agricultural chemical composition of the present invention is applied to the water surface of agricultural land and is suitable as a raw material for producing a granular water-surface-floating agricultural chemical composition having excellent spreadability of an agricultural active ingredient on the water surface after application.
The water-surface floating type agricultural chemical composition of the present invention is characterized by containing: an agricultural chemical active ingredient, and the above-mentioned spreading agent of the present invention.
The pesticidal active ingredient is not particularly limited as long as the activity is not impaired in the coexistence with water. Examples thereof include herbicides, insecticides, acaricides, nematicides, antiviral agents, plant growth regulators, bactericides, inducers, and insect repellents. These pesticidal active ingredients may be both water-soluble and water-insoluble. The pesticide active ingredient contained in the water-surface floating type pesticide composition of the present invention may be only 1 kind, or 2 or more kinds.
The content ratio of the above-mentioned pesticidal active ingredient and the spreading agent is not particularly limited.
The water-surface floating type pesticidal composition of the present invention may further contain other components such as an extender, a binder, a disintegration accelerator, a dispersant, an emulsifier, a liquid medium (water, glycol, paraffin oil, etc.), a stabilizer, and the like.
The water-surface floating type agricultural chemical composition of the present invention preferably contains an extender as another component. As extenders, it is possible to use: powders or particles of clay, silica, talc, clay, diatomaceous earth, silica, bentonite, calcium carbonate, barium sulfate, titanium dioxide, starch, lactose, potassium chloride, urea, hollow glass, white carbon, wood powder, cork powder, expandable white sand, microspheres, carboxymethylcellulose, and the like.
When the water-surface floating type agricultural chemical composition of the present invention contains an extender, the content ratios of the agricultural chemical active ingredient, the above-mentioned spreading agent of the present invention (the total amount of the above-mentioned diol compound (a), or the total amount of the diol compound (a) and the diol compound (B)) and the extender are preferably 0.1 to 80 mass%, 0.1 to 10 mass%, and 10 to 97 mass%, more preferably 0.2 to 70 mass%, 0.5 to 8 mass%, and 20 to 95 mass%, respectively, when the total amount of these components is 100 mass%.
The water-surface floating type agricultural chemical composition of the present invention may be a mixture (hereinafter referred to as "1 st agricultural chemical composition") having no shape in which the respective components are mixed as they are, or a granular molded article (granulated product) obtained by using the 1 st agricultural chemical composition. In the case of granules, the granules may or may not contain a liquid medium.
When the water-surface floating type agricultural chemical composition of the present invention is applied to the water surface of agricultural land, the composition is preferably a granulated product.
The water-surface floating type agricultural chemical composition of the present invention can be applied by manual application, mechanical application, or transfer application, as in the case of ordinary agricultural chemical granules, but it may be applied by so-called frame application in which the composition is applied from a ridge, a bank, or the like, or may be applied by wrapping the composition on water-soluble paper and applying the composition from the ridge, the bank, or the like. The water-soluble paper used for application is a film or sheet having solubility or dispersibility in water, and examples thereof include: a film or sheet formed from polyvinyl alcohol or a derivative thereof, pullulan, a sodium salt of carboxymethyl cellulose, polyethylene oxide or a derivative thereof, and the like, and among these, a film or sheet formed from polyvinyl alcohol or a derivative thereof is preferable.
In the case of producing the granulated product, the 1 st agricultural chemical composition may be processed by, for example, an extrusion molding machine, a screw type molding machine, a roll type molding machine, a plate type molding machine, or the like. The above-mentioned spreading agent of the present invention is excellent in the formability of the granulated product and the shape stability, and therefore, the obtained granular water-surface-floating agricultural chemical composition is easy to handle.
Examples
The present invention will be specifically described below with reference to examples. In the following description, "part" is based on mass unless otherwise specified.
1. Raw material of spreading agent for water-surface floating type pesticide composition
1-1. diol compound (A)
The compounds A-1 to A-25 and a-1 to a-4 obtained in the following synthetic examples 1 to 29 were used.
Synthesis example 1
160.3g (1 mol) of 2-butyl-2-ethyl-1, 3-propanediol was charged into an autoclave, and 0.3g (6 mmol equivalent to the raw material) of potassium hydroxide powder as a catalyst was added to the autoclave, and then the inside of the autoclave was sufficiently replaced with nitrogen. Then, while stirring them, 176g (4 moles) of ethylene oxide was introduced thereinto while maintaining the temperature of the reaction system at 130 to 150 ℃ to start the addition polymerization. Then, the mixture was aged at the same temperature for 1 hour to terminate the addition polymerization reaction. Thereafter, the catalyst of the reaction system was neutralized with phosphoric acid, and then, the reaction product was recovered by liquid chromatography separation. The obtained reaction product was analyzed by LC-MS, and as a result, it was found to be a compound represented by the following formula. Hereinafter, this compound is represented as A-1 (see Table 1).
ESI-MS：m/z＝337(M+H) +
Synthesis example 2
Compound a-2 (see table 1) was obtained by performing the same operation as in synthesis example 1, except that 4 moles of propylene oxide were used instead of 4 moles of ethylene oxide.
Synthesis example 3
Compound a-3 (see table 1) was obtained by performing the same operation as in synthesis example 1, except that a mixture of 2 moles of ethylene oxide and 2 moles of propylene oxide was used instead of 4 moles of ethylene oxide alone.
Synthesis example 4
160.3g (1 mol) of 2-butyl-2-ethyl-1, 3-propanediol was charged into an autoclave, 0.3g (6 mmol equivalent to the raw material) of potassium hydroxide powder as a catalyst was added, and the inside of the autoclave was sufficiently replaced with nitrogen. Then, the temperature of the reaction system was maintained at 130 to 150 ℃ while stirring them, 2 moles of ethylene oxide were introduced thereinto, and after aging at the same temperature for 1 hour, 2 moles of propylene oxide were introduced thereinto at 130 to 150 ℃ and aging at the same temperature for 1 hour was carried out to complete the addition polymerization. After completion of the reaction, the same operation as in Synthesis example 1 was carried out to obtain Compound A-4 (see Table 1).
Synthesis example 5
Compound a-5 (see table 1) was obtained by performing the same operation as in synthesis example 4, except that the order of ethylene oxide (2 moles) and propylene oxide (2 moles) introduced was reversed.
Synthesis example 6
Compound a-6 (see table 1) was obtained by performing the same operation as in synthesis example 1, except that the amount of ethylene oxide used was changed from 4 moles to 8 moles.
Synthesis example 7
Compound a-7 (see table 1) was obtained in the same manner as in synthesis example 1, except that 2, 4-diethyl-1, 3-pentanediol was used instead of 2-butyl-2-ethyl-1, 3-propanediol, and the amount of ethylene oxide used was changed from 4 moles to 6 moles.
Synthesis example 8
1 mol of 2, 4-diethyl-1, 3-pentanediol and 0.3g (6 mmol equivalent to the raw material) of potassium hydroxide powder as a catalyst were added, and then the inside of the autoclave was sufficiently replaced with nitrogen gas. Then, the temperature of the reaction system was maintained at 130 to 150 ℃ while stirring them, 1 mol of propylene oxide was injected, and after 1 hour of aging at the same temperature, 1 mol of ethylene oxide was injected at 130 to 150 ℃ and 1 hour of aging at the same temperature, thereby completing the addition polymerization. After completion of the reaction, the same operation as in Synthesis example 1 was carried out to obtain Compound A-8 (see Table 1).
Synthesis example 9
Compound a-9 (see table 1) was obtained by performing the same operation as in synthesis example 1, except that 2-methyl-1, 8-octanediol was used instead of 2-butyl-2-ethyl-1, 3-propanediol and the amount of ethylene oxide used was changed from 4 moles to 5 moles.
Synthesis example 10
Compound a-10 (see table 1) was obtained by performing the same operation as in synthesis example 1, except that 2-methyl-1, 8-octanediol was used instead of 2-butyl-2-ethyl-1, 3-propanediol and 7 moles of propylene oxide were used instead of 4 moles of ethylene oxide.
Synthesis example 11
Compound a-11 (see table 1) was obtained by performing the same operation as in synthesis example 1, except that the amount of ethylene oxide used was changed from 4 moles to 6 moles.
Synthesis example 12
Compound A-12 (see Table 1) was obtained by performing the same operation as in Synthesis example 1, except that 6 moles of propylene oxide were used instead of 4 moles of ethylene oxide
Synthesis example 13
Compound a-13 (see table 1) was obtained by the same operation as in synthesis example 1, except that 2-ethyl-1, 3-hexanediol was used instead of 2-butyl-2-ethyl-1, 3-propanediol, and the amount of ethylene oxide used was changed from 4 moles to 5 moles.
Synthesis example 14
Compound a-14 (see table 1) was obtained by performing the same operation as in synthesis example 1, except that 1, 8-octanediol was used instead of 2-butyl-2-ethyl-1, 3-propanediol and a mixture of 3 moles of ethylene oxide and 5 moles of propylene oxide was used instead of only 4 moles of ethylene oxide.
Synthesis example 15
Compound a-15 (see table 1) was obtained by performing the same operation as in synthesis example 1, except that 1, 9-nonanediol was used instead of 2-butyl-2-ethyl-1, 3-propanediol and the amount of ethylene oxide used was changed from 4 moles to 5 moles.
Synthesis example 16
Compound a-16 (see table 1) was obtained by performing the same operation as in synthesis example 1, except that the amount of ethylene oxide used was changed from 4 moles to 9 moles.
Synthesis example 17
Compound a-17 (see table 1) was obtained by performing the same operation as in synthesis example 4, except that the amount of ethylene oxide was changed to 4 moles and the amount of propylene oxide was changed to 5 moles.
Synthesis example 18
Compound a-18 (see table 1) was obtained by performing the same operation as in synthesis example 1, except that the amount of ethylene oxide used was changed from 4 moles to 1 mole.
Synthesis example 19
Compound a-19 (see table 1) was obtained by the same procedure as in synthesis example 1, except that 1, 10-decanediol was used instead of 2-butyl-2-ethyl-1, 3-propanediol and a mixture of 4 moles of ethylene oxide and 1 mole of propylene oxide was used instead of only 4 moles of ethylene oxide.
Synthesis example 20
Compound a-20 (see table 1) was obtained in the same manner as in synthesis example 1, except that 1, 12-dodecanediol was used instead of 2-butyl-2-ethyl-1, 3-propanediol and the amount of ethylene oxide used was changed from 4 moles to 8 moles.
Synthesis example 21
Compound a-21 (see table 1) was obtained by performing the same operation as in synthesis example 1, except that 1, 6-hexanediol was used instead of 2-butyl-2-ethyl-1, 3-propanediol.
Synthesis example 22
1 mol of 1, 10-decanediol and 0.3g (6 mmol equivalent based on the starting material) of potassium hydroxide powder as a catalyst were added, and then the inside of the autoclave was sufficiently replaced with nitrogen. Then, the temperature of the reaction system was maintained at 130 to 150 ℃ while stirring them, 5 moles of ethylene oxide was introduced, and after 1 hour of aging at the same temperature, 4 moles of propylene oxide were introduced at 130 to 150 ℃ and aged at the same temperature for 1 hour, thereby completing the addition polymerization. After completion of the reaction, the same operation as in Synthesis example 1 was carried out to obtain Compound A-22 (see Table 1).
Synthesis example 23
1 mol of 1, 2-tetradecanediol and 0.3g (6 mmol equivalent to the starting material) of potassium hydroxide powder as a catalyst were added, and then the inside of the autoclave was sufficiently replaced with nitrogen gas. Then, the temperature of the reaction system was maintained at 130 to 150 ℃ while stirring them, 2 moles of propylene oxide were added thereto, and after aging at the same temperature for 1 hour, 4 moles of ethylene oxide were added thereto at 130 to 150 ℃ and aging at the same temperature for 1 hour was carried out to complete the addition polymerization. After completion of the reaction, the same operation as in Synthesis example 1 was carried out to obtain Compound A-23 (see Table 1).
Synthesis example 24
Compound a-24 (see table 1) was obtained by performing the same operation as in synthesis example 1, except that 1, 2-tetradecanediol was used instead of 2-butyl-2-ethyl-1, 3-propanediol and the amount of ethylene oxide used was changed from 4 moles to 10 moles.
Synthesis example 25
Compound a-25 (see table 1) was obtained in the same manner as in synthesis example 1, except that 1, 6-hexanediol was used instead of 2-butyl-2-ethyl-1, 3-propanediol and 1 mol of propylene oxide was used instead of 4 mol of ethylene oxide.
Synthesis example 26
Compound a-1 (see table 1) was obtained by performing the same operation as in synthesis example 1, except that a mixture of 6 moles of ethylene oxide and 6 moles of propylene oxide was used instead of 4 moles of ethylene oxide alone.
Synthesis example 27
Compound a-2 (see table 1) was obtained by the same operation as in synthesis example 1, except that 2-ethyl-1, 3-hexanediol was used instead of 2-butyl-2-ethyl-1, 3-propanediol, and the amount of ethylene oxide used was changed from 4 moles to 14 moles.
Synthesis example 28
Compound a-3 (see table 1) was obtained in the same manner as in synthesis example 1, except that 1, 4-butanediol was used instead of 2-butyl-2-ethyl-1, 3-propanediol and the amount of ethylene oxide used was changed from 4 moles to 6 moles.
Synthesis example 29
Compound a-4 (see table 1) was obtained by performing the same operation as in synthesis example 1, except that 1, 2-hexadecanediol was used instead of 2-butyl-2-ethyl-1, 3-propanediol.
[ Table 1]
1-2. diol compound (B)
The compounds B-1 to B-4 obtained in the following synthetic examples 30 to 33 were used.
Synthesis example 30
160.3g (1 mol) of 2-butyl-2-ethyl-1, 3-propanediol was charged into an autoclave, and 0.9g (18 mmol equivalent to the raw material) of potassium hydroxide powder as a catalyst was added thereto, and then the inside of the autoclave was sufficiently replaced with nitrogen. Then, the reaction temperature was maintained at 130 to 150 ℃ with stirring, 176g (4 mol) of ethylene oxide was introduced thereinto under pressure to conduct addition polymerization, and the reaction mixture was aged at the same temperature for 1 hour to complete the addition polymerization. Then, the catalyst was neutralized with phosphoric acid, and the by-product was separated by liquid chromatography to obtain a diol compound B-1 represented by the following formula (see table 2).
Synthesis example 31
Diol compound B-2 (see table 2) was obtained in the same manner as in synthesis example 30, except that 2, 4-diethyl-1, 3-pentanediol was used instead of 2-butyl-2-ethyl-1, 3-propanediol and the amount of ethylene oxide used was changed from 4 moles to 6 moles.
Synthesis example 32
The same operation as in synthesis example 30 was carried out except for using 2-methyl-1, 8-octanediol instead of 2-butyl-2-ethyl-1, 3-propanediol and using 8 moles of propylene oxide instead of 4 moles of ethylene oxide, to obtain a diol compound B-3 (see table 2).
Synthesis example 33
Diol compound B-4 (see table 2) was obtained in the same manner as in synthesis example 30, except that the amount of ethylene oxide used was changed from 4 moles to 10 moles.
[ Table 2]
TABLE 2
2. Preparation of spreading agent for water-surface floating type pesticide composition
Examples 1-1 to 1-31 and comparative examples 1-1 to 1-8
Using only the diol compound (a) obtained above or using the diol compounds (a) and (B), a spreading agent for a water-floating agricultural chemical composition was obtained (see table 3). The substances obtained in examples 1-1 to 1-31 were used as the water-surface floating type agricultural chemical composition spreaders C-1 to C-31, and the substances obtained in comparative examples 1-1 to 1-8 were used as the water-surface floating type agricultural chemical composition spreaders C-1 to C-8.
[ Table 3]
TABLE 3
3. Production and evaluation of Water surface Floating type pesticidal composition
The above-obtained spreading agent for a water-surface floating type agricultural chemical composition, the following agricultural chemical active ingredient and extender, and a small amount of water were used to produce a granular water-surface floating type agricultural chemical composition. Then, evaluation was performed assuming application to agricultural land having a water surface.
(pesticidal active ingredient)
Z-1: cafenstrole (cafenstrole)
Z-2: bensulfuron-methyl (Londax Power)
Z-3: weeding method (Daimuron)
Z-4: pretilachlor (Pretilachlor)
Z-5: diazinon (Diazinon)
Z-6: tricyclozole (Tricyclazole)
(extender)
J-1: clay powder
J-2: calcium carbonate powder
J-3: potassium chloride powder
J-4: talcum powder
J-5: bentonite powder
J-6: diatomaceous earth powder
J-7: lactose powder
J-8: starch powder
J-9: white carbon powder
J-10: hollow glass particle
J-11: wood flour
J-12: cork powder
J-13: foaming white sand powder
J-14: microspheres
J-15: carboxymethyl cellulose powder
Example 2-1
After 20 parts of cafenstrole (Z-1) and 31 parts of clay (J-1) and 10 parts of bentonite (J-5) are uniformly mixed with 35 parts of hollow glass (J-10), the mixture is thoroughly mixed with 4 parts of a spreader (C-1) and a small amount of water. Next, the resulting kneaded mixture was subjected to extrusion molding using a basket pelletizer (KAR-75, manufactured by Katsui chemical Co., Ltd.) equipped with a wire mesh having a pore diameter of 1.0 mm. Then, the molded product was dried in a thermostat at 50 ℃ to complete the granules into particles having a length of 2 to 4mm, thereby producing cylindrical granular water-surface floating-type pesticidal compositions (see table 4).
Both the water-surface floating type agricultural chemical composition immediately after production and 0.2g of the water-surface floating type agricultural chemical composition stored at 54 ℃ for 4 weeks were used as samples, and the samples were put into tap water (depth 2cm) stored in a container shown in fig. 1, and the spreading distance, spreading speed, spreadability, and disintegration state were evaluated by the following methods. The container 1 of fig. 1 is made of stainless steel having a longitudinal length of 20cm, a lateral length of 100cm, and a depth of 4cm, and is divided into two parts by a partition 3 having a length corresponding to 90cm from one end.
(1) Spreading distance
After the sample was put into the water at the x mark of fig. 2 and 3, the distance that the pellets floated on the water surface and moved within 2 minutes was measured (in the case of folding back at the Δ mark of fig. 2 and 3, 200cm was maximum). This operation was performed 5 times, and the average value of the distances was evaluated according to the following criteria.
(evaluation criteria)
Very good: over 170cm
O: 130cm or more and less than 170cm
X: below 130cm
(2) Speed of spreading
After the sample was put into the place marked by x in fig. 2 and 3, the time required for the granular material floating on the water surface to spread until marked by Δ was measured. The measurement was performed 5 times, and the development rate was calculated from the average value thereof according to the following calculation formula and evaluated according to the following criteria.
The spreading speed (cm/s) is 100 (cm)/required time(s)
(evaluation criteria)
Excellent: 6 cm/s or more
O: 4 cm/sec or more and less than 6 cm/sec
X: less than 4 cm/sec
(3) Spreading property
After the sample was put into the x mark of fig. 2 and 3, the appearance at the time of disintegration was visually observed and evaluated according to the following criteria.
(evaluation criteria)
Very excellent: spread with irregular movement and rotate sharply when the granules disintegrate
Excellent: spread with irregular movement and rotate when the granules are disintegrated
O: spread with irregular movement and not rotate when disintegrating
X: spread in straight line, and does not rotate during disintegration
(4) Disintegrating state
After the sample was put into the x mark of fig. 2 and 3, the appearance of the powder disintegrated and dispersed in water was visually observed from above, and evaluated according to the following criteria.
(evaluation criteria)
O: no powder aggregation and uniform dispersion on water surface
And (delta): some of the visible powder aggregates or some of the visible powder is unevenly distributed
X: most of the powder is visibly aggregated or the powder is visibly unevenly distributed
Examples 2-2 to 2-31 and comparative examples 2-1 to 2-16
Using the raw materials shown in tables 4 to 8, a cylindrical granular water-surface floating type agricultural chemical composition was produced by extrusion molding in the same manner as in example 2-1. Thereafter, various evaluations were performed. The results are also shown in tables 4 to 8.
[ Table 4]
TABLE 4
[ Table 5]
TABLE 5
[ Table 6]
TABLE 6
[ Table 7]
TABLE 7
[ Table 8]
TABLE 8
In tables 4 to 6, examples 2-1 to 2-31 are examples of the agricultural chemical composition containing the spreading agent for a water-surface floating type agricultural chemical composition containing the diol compound (a) of the present invention, and are good in all of the spreading distance, spreading speed, spreading property and disintegration state. Wherein, in particular, in examples 2-1 to 2-13, R in the above formula (1) is used 1 As an example of the diol compound (A) of the present invention, a compound which is an alkylene group having 8 or 9 carbon atoms and s is an integer of 2 to 8 has higher performance.
On the other hand, comparative examples 2-1 to 2-8 in tables 7 and 8 are examples of the agricultural chemical composition containing the spreading agent for a water-surface floating type agricultural chemical composition not containing the diol compound (a) of the present invention, and sufficient performance was not obtained.
Industrial applicability
The above-mentioned spreading agent for a water-surface-floating agricultural chemical composition of the present invention is used in combination with an agricultural chemical active material, an extender and the like to form a water-surface-floating agricultural chemical composition, and is suitable for forming granules, for example. Further, if the granules are sprayed on agricultural land having a water surface, the active ingredients of agricultural chemicals can be spread sufficiently. Therefore, the water-surface floating type pesticidal composition of the present invention is useful for application to agricultural land having a water surface.
Claims (7)
1. A water-surface floating type pesticidal composition characterized by comprising: an agricultural chemical active ingredient, and a compound represented by the following general formula (1),
HO-R 1 -O-G 1 -H (1)
in the formula, R 1 Is an alkylene group having 6 to 14 carbon atoms, G 1 Is- (R) 5 O) s -a group having a valence of 2, R 5 Is an alkylene group having 2 or 3 carbon atoms, s is an integer of 1 to 10, and s is 2 or more, - (R) 5 O) s R in (A-C) 5 Optionally all the same or different.
2. The water-surface floating type pesticidal composition according to claim 1, wherein in the compound of the general formula (1), R is 1 Is an alkylene group having 8 to 12 carbon atoms.
3. The water-surface floating type pesticidal composition according to claim 1 or 2, wherein in the compound of the general formula (1), R 1 Is an alkylene group having 8 or 9 carbon atoms, and s is an integer of 2 to 8.
4. The water surface floating type pesticidal composition according to claim 1 or 2, further comprising a compound represented by the following general formula (2),
H-G 2 -O-R 2 -O-G 3 -H (2)
in the formula, R 2 Is an alkylene group having 6 to 14 carbon atoms, G 2 Is- (OR) 7 ) t -a group having a valence of 2, R 7 Is an alkylene group having 2 OR 3 carbon atoms, t is an integer of 1 to 10, and when t is 2 OR more, - (OR) 7 ) t R in (A-C) 7 Optionally all of the same or different, G 3 Is- (R) 9 O) u -a group having a valence of 2, R 9 Is an alkylene group having 2 or 3 carbon atoms, u is an integer of 1 to 10, and u is 2 or more, - (R) 9 O) u R in (A-C) 9 Optionally all the same or different.
5. The water-surface-floating pesticide composition according to claim 4, wherein the content ratio of the compound represented by the general formula (1) and the compound represented by the general formula (2) is 40 to 99% by mass and the content ratio of the compound represented by the general formula (2) is 1 to 60% by mass, based on 100% by mass of the total content of the compounds.
6. The water surface floating type pesticidal composition according to claim 1 or 2, which further contains an extender.
7. The water-surface-floating pesticide composition according to claim 6, wherein the content ratio of the pesticide active ingredient, the compound represented by the general formula (1), and the extender is 0.1 to 80% by mass, 0.1 to 10% by mass of the compound represented by the general formula (1), and 10 to 97% by mass of the extender, when the total content of these components is 100% by mass.
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| JP2020090052A JP6739129B1 (en) | 2020-05-22 | 2020-05-22 | Spreading agent for waterborne floating pesticide composition and pesticide composition containing the same |
| JP2020-090052 | 2020-05-22 | ||
| CN202110534005.2A CN113693061B (en) | 2020-05-22 | 2021-05-17 | Spreading agent for water-surface floating type pesticide composition and pesticide composition containing same |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007039344A (en) * | 2005-08-01 | 2007-02-15 | Takemoto Oil & Fat Co Ltd | Spreader for water surface-floating type agrochemical composition and water surface-floating type agrochemical composition |
| JP2009114102A (en) * | 2007-11-05 | 2009-05-28 | Sumitomo Chemical Co Ltd | Water surface-floating agrochemical granular composition, and pouched agrochemical formulation for paddy field treatment comprising the same |
| JP2009173575A (en) * | 2008-01-24 | 2009-08-06 | Sumitomo Chemical Co Ltd | Method for producing water surface-floating agrochemical granule |
| JP2010143849A (en) * | 2008-12-18 | 2010-07-01 | Takemoto Oil & Fat Co Ltd | Aqueous suspended agrochemical composition for paddy field |
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| US2407205A (en) * | 1943-02-11 | 1946-09-03 | Carbide & Carbon Chem Corp | Insect repellents |
| US3726910A (en) * | 1970-04-01 | 1973-04-10 | Dow Chemical Co | (((alkylthio)alkyl)thio)phenyl carbamates |
| JP4889283B2 (en) * | 2005-11-11 | 2012-03-07 | 株式会社Ａｄｅｋａ | Antibacterial composition and cosmetics and cleaning agents containing the same |
| JP4991220B2 (en) * | 2006-09-06 | 2012-08-01 | 三洋化成工業株式会社 | Antibacterial agent for cosmetics |
| JP5240501B2 (en) * | 2007-03-19 | 2013-07-17 | 株式会社リコー | Ink set, ink cartridge, ink jet recording method, and ink jet recording apparatus |
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007039344A (en) * | 2005-08-01 | 2007-02-15 | Takemoto Oil & Fat Co Ltd | Spreader for water surface-floating type agrochemical composition and water surface-floating type agrochemical composition |
| JP2009114102A (en) * | 2007-11-05 | 2009-05-28 | Sumitomo Chemical Co Ltd | Water surface-floating agrochemical granular composition, and pouched agrochemical formulation for paddy field treatment comprising the same |
| JP2009173575A (en) * | 2008-01-24 | 2009-08-06 | Sumitomo Chemical Co Ltd | Method for producing water surface-floating agrochemical granule |
| TW200938085A (en) * | 2008-01-24 | 2009-09-16 | Sumitomo Chemical Co | Method for manufacturing pesticide granules |
| JP2010143849A (en) * | 2008-12-18 | 2010-07-01 | Takemoto Oil & Fat Co Ltd | Aqueous suspended agrochemical composition for paddy field |
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| JP6739129B1 (en) | 2020-08-12 |
| JP2021183582A (en) | 2021-12-02 |
| CN113693061A (en) | 2021-11-26 |
| CN113693061B (en) | 2022-07-08 |
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