JP2009530289A - 農業用分散剤として有用なポリエーテルアミンのコームポリマー誘導体 - Google Patents
農業用分散剤として有用なポリエーテルアミンのコームポリマー誘導体 Download PDFInfo
- Publication number
- JP2009530289A JP2009530289A JP2009500459A JP2009500459A JP2009530289A JP 2009530289 A JP2009530289 A JP 2009530289A JP 2009500459 A JP2009500459 A JP 2009500459A JP 2009500459 A JP2009500459 A JP 2009500459A JP 2009530289 A JP2009530289 A JP 2009530289A
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- JP
- Japan
- Prior art keywords
- composition
- dispersant
- succinic anhydride
- water
- pesticide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000002270 dispersing agent Substances 0.000 title claims abstract description 84
- 150000001412 amines Chemical class 0.000 title claims abstract description 44
- 239000004721 Polyphenylene oxide Substances 0.000 title claims description 16
- 229920000570 polyether Polymers 0.000 title claims description 16
- 229920000642 polymer Polymers 0.000 title description 4
- 239000000203 mixture Substances 0.000 claims abstract description 71
- 239000011347 resin Substances 0.000 claims abstract description 46
- 229920005989 resin Polymers 0.000 claims abstract description 46
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims abstract description 32
- 229940014800 succinic anhydride Drugs 0.000 claims abstract description 32
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 31
- 238000000034 method Methods 0.000 claims description 37
- 239000000575 pesticide Substances 0.000 claims description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 29
- 229920000147 Styrene maleic anhydride Polymers 0.000 claims description 12
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 11
- 239000000047 product Substances 0.000 claims description 10
- 239000000080 wetting agent Substances 0.000 claims description 9
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 8
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 7
- 239000002917 insecticide Substances 0.000 claims description 7
- 229920005575 poly(amic acid) Polymers 0.000 claims description 7
- 239000000178 monomer Substances 0.000 claims description 6
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 5
- 239000012530 fluid Substances 0.000 claims description 5
- 239000004009 herbicide Substances 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- 239000003429 antifungal agent Substances 0.000 claims description 4
- 229940121375 antifungal agent Drugs 0.000 claims description 4
- 230000002363 herbicidal effect Effects 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 238000005507 spraying Methods 0.000 claims description 3
- 239000000375 suspending agent Substances 0.000 claims description 3
- 239000012872 agrochemical composition Substances 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- 239000002518 antifoaming agent Substances 0.000 claims 3
- 239000002577 cryoprotective agent Substances 0.000 claims 3
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 claims 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 238000009472 formulation Methods 0.000 abstract description 19
- 239000004546 suspension concentrate Substances 0.000 abstract description 3
- WTFAGPBUAGFMQX-UHFFFAOYSA-N 1-[2-[2-(2-aminopropoxy)propoxy]propoxy]propan-2-amine Chemical compound CC(N)COCC(C)OCC(C)OCC(C)N WTFAGPBUAGFMQX-UHFFFAOYSA-N 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 150000008064 anhydrides Chemical class 0.000 description 8
- -1 ethylene Chemical class 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 150000001336 alkenes Chemical class 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- 241000238631 Hexapoda Species 0.000 description 3
- 239000005802 Mancozeb Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 230000000843 anti-fungal effect Effects 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 150000003949 imides Chemical class 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- SXYOAESUCSYJNZ-UHFFFAOYSA-L zinc;bis(6-methylheptoxy)-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [Zn+2].CC(C)CCCCCOP([S-])(=S)OCCCCCC(C)C.CC(C)CCCCCOP([S-])(=S)OCCCCCC(C)C SXYOAESUCSYJNZ-UHFFFAOYSA-L 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 229930188620 butyrolactone Natural products 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000002538 fungal effect Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 229940102213 injectable suspension Drugs 0.000 description 2
- 235000021073 macronutrients Nutrition 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000011785 micronutrient Substances 0.000 description 2
- 235000013369 micronutrients Nutrition 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 239000005648 plant growth regulator Substances 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 2
- 239000001384 succinic acid Substances 0.000 description 2
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 1
- HNBUVWSTMWNESI-OLGQORCHSA-N (Z)-2-methylbut-2-enedioic acid 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O.OC(=O)C(/C)=C\C(O)=O HNBUVWSTMWNESI-OLGQORCHSA-N 0.000 description 1
- ZZXUZKXVROWEIF-UHFFFAOYSA-N 1,2-butylene carbonate Chemical compound CCC1COC(=O)O1 ZZXUZKXVROWEIF-UHFFFAOYSA-N 0.000 description 1
- HQSMEHLVLOGBCK-UHFFFAOYSA-N 1-ethenylsulfinylethene Chemical compound C=CS(=O)C=C HQSMEHLVLOGBCK-UHFFFAOYSA-N 0.000 description 1
- AXGOOCLYBPQWNG-UHFFFAOYSA-N 3-ethylfuran-2,5-dione Chemical compound CCC1=CC(=O)OC1=O AXGOOCLYBPQWNG-UHFFFAOYSA-N 0.000 description 1
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000005745 Captan Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000007798 antifreeze agent Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229940117949 captan Drugs 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
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- 230000003750 conditioning effect Effects 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- WOLATMHLPFJRGC-UHFFFAOYSA-N furan-2,5-dione;styrene Chemical compound O=C1OC(=O)C=C1.C=CC1=CC=CC=C1 WOLATMHLPFJRGC-UHFFFAOYSA-N 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- KETWBQOXTBGBBN-UHFFFAOYSA-N hex-1-enylbenzene Chemical compound CCCCC=CC1=CC=CC=C1 KETWBQOXTBGBBN-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 230000003050 macronutrient Effects 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- YBEFXFBAXWUBNQ-UHFFFAOYSA-N n-methylmethanamine;propan-1-amine Chemical compound CNC.CCCN YBEFXFBAXWUBNQ-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000003090 pesticide formulation Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003440 styrenes Chemical group 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical group O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- MBBWTVUFIXOUBE-UHFFFAOYSA-L zinc;dicarbamodithioate Chemical compound [Zn+2].NC([S-])=S.NC([S-])=S MBBWTVUFIXOUBE-UHFFFAOYSA-L 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F257/00—Macromolecular compounds obtained by polymerising monomers on to polymers of aromatic monomers as defined in group C08F12/00
- C08F257/02—Macromolecular compounds obtained by polymerising monomers on to polymers of aromatic monomers as defined in group C08F12/00 on to polymers of styrene or alkyl-substituted styrenes
-
- 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
- A01N25/08—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 solids as carriers or diluents
- A01N25/10—Macromolecular compounds
-
- 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
-
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Abstract
Description
本発明は現代の分散剤の前記に考察された不利及び/又は欠点に対処する。新規発明分散剤は、典型的には低価格で、製造が容易で、多数の適用により有効である。より大量の固形物がより容易に分散され、より長い棚寿命をもち、それにより製造業者に経費節減をもたらすことができるような、農業用化学薬品のためのより良い分散剤が必要である。
JEFFAMINE(R)アミンのようなアミンと反応された、樹脂を含有する無水琥珀酸から誘導される分散剤により、高い固形物、低い粘度をもつ、農薬の安定な分散物を製造することができる。JEFFAMINEはHuntsman Corporationの登録商標である。
を有する。
第1部
ブチロラクトン(20.9部)及びSMA−1000(10.4部)の溶液を乾燥雰囲気下、45Cで12時間、物質を混合することにより調製した。この溶液に、JEFFAMINE(R)507アミン(89.5部)を15分間、連続して撹拌しながら添加して、アミンとSMAの反応生成物を形成し、それは分散剤と呼ぶことができる。抗カビ・真菌剤のマンコゼブ(亜鉛塩とのマンガン・エチレンビス(ジチオカルバメート)(ポリマー性)錯体)を含有する調合物をTERWET(R)1004アルファオレフィンスルホネート界面活性剤(1部)(TERWETはHuntsman Petrochemical Corporationの登録商標である)、分散剤(3部)、エチレングリコール(4部)、水(36部)及びマンコゼブ(56部)から製造した。これを手動で混合し、薄い、注入可能な懸濁物をもたらした。
第1部に対して、前記と同様なブレンドを、Dispersant 8321−100Cの代りに分散剤MORWER(R)D−425を使用して、同様な方法により製造した。生成物は注入不可能なペーストであった。
Dispersant 8321−100Cの有用性を更に示すために、以下:水(40部)、TERWET(R)1004界面活性剤(1部)、エチレングリコール(5部)及びマンコゼブ(54部)のような、分散剤を含有しないブレンドを調製した。Dispersant 8321−100Cの欠乏のために、生成物は流動しないであろうペーストであり、混合が非常に困難であった。
コームポリマーの分散剤を、57部のPIBSA(OLOA(R)15500無灰分散剤中間体の名でChevron Oroniteから市販)を43部のJEFFAMINE(R)XTJ−506アミンと反応させることにより、PIBSA及びJEFFAMINE(R)XTJ−506アミンから調製した。反応は、2成分を合わせ、混合物を60℃に加熱しながら、激しく混合することにより実施した。次に反応生成物を100部のプロピレングリコールで希釈すると、重量に基づいて50%の有効な分散剤を含有するブレンドを与えた。
本実施例において、本発明の分散剤を使用して、多数の農業用組成物を調製した。必要とされる多数の特定のサンプルの調製を促進するために、各有効物質の作業ストック懸濁物を調製し、3〜4ミクロンの平均粒度が達成するまで粉砕した。このストック懸濁物は工業的有効物質(48部)、湿潤化剤(1部)及び水(49.75部)からなった。後に添加するために1.25重量部の分散剤のための「余裕(room)」を残した。各ストック懸濁物を8部分の125グラムに分割した。研究中、各分散剤を有効物質の重量に基づいて1.56グラムの分散剤を使用するように懸濁物の準サンプルの1つに添加した。分散剤を高剪断(ローター−ステーター)ミキサーの使用により取り入れた。1つのサンプルは対照としての使用のために分散剤で処置しなかった。ガム又は粘土のような更なる懸濁安定剤は研究されている系に添加しなかった。各最終懸濁物の粘度を、Brookfield DVII+粘土計及び適当なスピンドロウ(LV−1、LV−2又はLV−3)を使用して測定した。分散剤の効果を測定するために、分散剤を含む対応するサンプルに、分散剤を含まないサンプルの粘度を比較した。データは、本発明の分散剤が生成された農業用組成物に粘度減少を提供することを示す。
Claims (48)
- 少なくとも1種の無水琥珀酸含有樹脂及び少なくとも1種のアミンの反応生成物を含んでなる水溶性分散剤、並びに
少なくとも1種の非水溶性農薬:
を含んでなる農業用組成物。 - 農薬が流体中に懸濁される、請求項1の組成物。
- 少なくとも1種の無水琥珀酸含有樹脂が、無水ポリイソブテニル琥珀酸、スチレン無水マレイン酸、それらの誘導体及びそれらの組み合わせ物:よりなる群から選択される、請求項1の組成物。
- 少なくとも1種の無水琥珀酸含有樹脂が少なくとも1種のアクリル酸又はアクリル酸誘導体を含んでなる、請求項1の組成物。
- 少なくとも1種の無水琥珀酸含有樹脂が、メチルアクリレート、アクリロニトリル、それらの誘導体及びそれらの組み合わせ物:よりなる群から選択されるモノマーの生成物を含んでなる、請求項1の組成物。
- 少なくとも1種のアミンがポリエーテルモノアミンを含んでなる、請求項1の組成物。
- 少なくとも1種のアミンがジメチルアミノプロピルアミンを含んでなる、請求項1の組成物。
- 更に水を含んでなる、請求項1の組成物。
- 更に湿潤化剤を含んでなる、請求項1の組成物。
- 農薬が殺虫剤、除草剤又は抗カビ・真菌剤である、請求項1の組成物。
- 分散剤が約5,000〜約20,000の分子量を有する、請求項1の組成物。
- 分散剤がアミド酸又はポリアミド酸反応生成物である、請求項1の組成物。
- 組成物が約0.5%〜約4%の分散剤を含んでなる、請求項1の組成物。
- 約10%〜約50%の農薬、約0.5%〜約4%の分散剤、0〜約3%の湿潤化剤、0〜約10%の凍結防止剤、0〜約10%の沈殿防止剤、0〜約1%の消泡剤及び残りの水を含有する、請求項1の組成物。
- 少なくとも1種の無水琥珀酸含有樹脂及び少なくとも1種のアミンの反応生成物を含んでなる第1の成分を提供し、
少なくとも1種の農薬を含んでなる第2の成分を提供し、そして
第1の成分及び第2の成分を接触させる工程:
を含んでなる工程により生成される農業用組成物。 - 第1の成分及び第2の成分を接触させる工程が第1の成分及び第2の成分を液体の連続相中で接触させる工程を含んでなる、請求項15の組成物。
- 少なくとも1種の無水琥珀酸含有樹脂及び少なくとも1種のアミンの反応生成物を含んでなる水溶性分散剤を、少なくとも1種の非水溶性農薬と混合して、組成物を形成する工程:を含んでなる、分散された農薬組成物を製造する方法。
- 農薬が流体中に懸濁される、請求項17の方法。
- 無水琥珀酸含有樹脂が無水ポリイソブテニル琥珀酸、スチレン無水マレイン酸、それらの誘導体及びそれらの組み合わせ物:よりなる群から選択される、請求項17の方法。
- 無水琥珀酸含有樹脂が少なくとも1種のアクリル酸を含んでなる、請求項17の方法。
- 無水琥珀酸含有樹脂がメチルアクリレート、アクリロニトリル、それらの誘導体及びそれらの組み合わせ物:よりなる群から選択されるモノマーの生成物を含んでなる、請求項17の方法。
- 少なくとも1種のアミンがポリエーテルモノアミンを含んでなる、請求項17の方法。
- アミンがジメチルアミノプロピルアミンを含んでなる、請求項17の方法。
- 組成物が更に水を含んでなる、請求項17の方法。
- 組成物が更に湿潤化剤を含んでなる、請求項17の方法。
- 農薬が殺虫剤、除草剤又は抗カビ・真菌剤である、請求項17の方法。
- 分散剤が約5,000〜約20,000の分子量を有する、請求項17の方法。
- 分散剤がアミド酸又はポリアミド酸反応生成物である、請求項17の方法。
- 組成物が約0.5%〜約4%の分散剤を含んでなる、請求項17の方法。
- 組成物が約10%〜約50%の農薬、約0.5%〜約4%の分散剤、0〜約3%の湿潤化剤、0〜約10%の凍結防止剤、0〜約10%の沈殿防止剤、0〜約1%の消泡剤及び残りの水を含んでなる、請求項17の方法。
- 少なくとも1種の無水琥珀酸含有樹脂及び少なくとも1種のアミンの反応生成物を含んでなる水溶性分散剤並びに少なくとも1種の非水溶性農薬を含んでなる濃厚組成物を、水で希釈して、組成物水溶液を形成し、そして基体(substrate)に組成物水溶液を適用する工程:を含んでなる、基体を処理する方法。
- 組成物が噴霧により適用される、請求項31の方法。
- 農薬が流体中に懸濁される、請求項31の方法。
- 無水琥珀酸含有樹脂が無水ポリイソブテニル琥珀酸、スチレン無水マレイン酸、それらの誘導体及びそれらの組み合わせ物:よりなる群から選択される、請求項31の方法。
- 無水琥珀酸含有樹脂が少なくとも1種のアクリル酸を含んでなる、請求項31の方法。
- 無水琥珀酸含有樹脂がメチルアクリレート、アクリロニトリル、それらの誘導体及びそれらの組み合わせ物:よりなる群から選択されるモノマーの生成物を含んでなる、請求項31の方法。
- 少なくとも1種のアミンがポリエーテルモノアミンを含んでなる、請求項31の方法。
- アミンがジメチルアミノプロピルアミンを含んでなる、請求項31の方法。
- 組成物が更に水を含んでなる、請求項31の方法。
- 組成物が更に湿潤化剤を含んでなる、請求項31の方法。
- 農薬が殺虫剤、除草剤又は抗カビ・真菌剤である、請求項31の方法。
- 分散剤が約5,000〜約20,000の分子量を有する、請求項31の方法。
- 分散剤がアミド酸又はポリアミド酸反応生成物である、請求項31の方法。
- アミド酸反応生成物が中和されたカルボン酸基を含んでなる、請求項43の方法。
- ポリアミド酸反応生成物が少なくとも1個の中和されたカルボン酸基を含んでなる、請求項43の方法。
- ポリアミド酸反応生成物が中和されたカルボン酸基を含んでなる、請求項43の方法。
- 組成物が約0.5%〜約4%の分散剤を含んでなる、請求項31の方法。
- 組成物が約10%〜約50%の農薬、約0.5%〜約4%の分散剤、0〜約3%の湿潤化剤、0〜約10%の凍結防止剤、0〜約10%の沈殿防止剤、0〜約1%の消泡剤及び残りの水を含んでなる、請求項31の方法。
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WO2007109051A2 (en) | 2007-09-27 |
AU2007227608A1 (en) | 2007-09-27 |
CN101431899A (zh) | 2009-05-13 |
CN101431899B (zh) | 2012-11-28 |
EP1996024A4 (en) | 2013-12-11 |
MX2008011697A (es) | 2009-01-26 |
AU2007227608B2 (en) | 2012-08-16 |
CA2644698A1 (en) | 2007-09-27 |
US8247353B2 (en) | 2012-08-21 |
CA2644698C (en) | 2014-06-03 |
EP1996024B1 (en) | 2018-08-22 |
US8420573B2 (en) | 2013-04-16 |
US20070244216A1 (en) | 2007-10-18 |
JP5315231B2 (ja) | 2013-10-16 |
WO2007109051A3 (en) | 2007-12-13 |
US20120264610A1 (en) | 2012-10-18 |
ES2691549T3 (es) | 2018-11-27 |
EP1996024A2 (en) | 2008-12-03 |
PL1996024T3 (pl) | 2019-01-31 |
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