JPS6379802A - Agricultural chemical composition containing cyclodextrin - Google Patents
Agricultural chemical composition containing cyclodextrinInfo
- Publication number
- JPS6379802A JPS6379802A JP22542486A JP22542486A JPS6379802A JP S6379802 A JPS6379802 A JP S6379802A JP 22542486 A JP22542486 A JP 22542486A JP 22542486 A JP22542486 A JP 22542486A JP S6379802 A JPS6379802 A JP S6379802A
- Authority
- JP
- Japan
- Prior art keywords
- cyclodextrin
- parts
- active ingredient
- agricultural chemical
- role name
- 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.)
- Pending
Links
- 229920000858 Cyclodextrin Polymers 0.000 title claims abstract description 60
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 239000000203 mixture Substances 0.000 title claims abstract description 20
- 239000003905 agrochemical Substances 0.000 title claims abstract description 13
- 239000001116 FEMA 4028 Substances 0.000 claims abstract description 34
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 claims abstract description 34
- 235000011175 beta-cyclodextrine Nutrition 0.000 claims abstract description 34
- 229960004853 betadex Drugs 0.000 claims abstract description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000000428 dust Substances 0.000 claims abstract description 6
- 239000008187 granular material Substances 0.000 claims abstract description 6
- 239000004563 wettable powder Substances 0.000 claims abstract description 5
- 239000000725 suspension Substances 0.000 claims abstract description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 22
- 239000000843 powder Substances 0.000 claims description 16
- 239000012868 active agrochemical ingredient Substances 0.000 claims description 9
- 239000012872 agrochemical composition Substances 0.000 claims description 5
- 230000000391 smoking effect Effects 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 abstract description 22
- 238000009472 formulation Methods 0.000 abstract description 8
- 238000002156 mixing Methods 0.000 abstract description 6
- 239000002552 dosage form Substances 0.000 abstract description 4
- 239000002917 insecticide Substances 0.000 abstract description 4
- 239000005746 Carboxin Substances 0.000 abstract description 3
- GYSSRZJIHXQEHQ-UHFFFAOYSA-N carboxin Chemical compound S1CCOC(C)=C1C(=O)NC1=CC=CC=C1 GYSSRZJIHXQEHQ-UHFFFAOYSA-N 0.000 abstract description 3
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 abstract description 3
- 239000004009 herbicide Substances 0.000 abstract description 3
- DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 abstract description 3
- -1 beta-cyclodextrin Chemical compound 0.000 abstract description 2
- 230000004071 biological effect Effects 0.000 abstract description 2
- 230000002363 herbicidal effect Effects 0.000 abstract description 2
- 238000007796 conventional method Methods 0.000 abstract 1
- 239000002316 fumigant Substances 0.000 abstract 1
- 230000002070 germicidal effect Effects 0.000 abstract 1
- 230000005764 inhibitory process Effects 0.000 abstract 1
- 230000000052 comparative effect Effects 0.000 description 19
- 230000002262 irrigation Effects 0.000 description 16
- 238000003973 irrigation Methods 0.000 description 16
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 11
- 235000012239 silicon dioxide Nutrition 0.000 description 11
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 10
- 239000004927 clay Substances 0.000 description 10
- QPPQHRDVPBTVEV-UHFFFAOYSA-N isopropyl dihydrogen phosphate Chemical compound CC(C)OP(O)(O)=O QPPQHRDVPBTVEV-UHFFFAOYSA-N 0.000 description 6
- 229910000019 calcium carbonate Inorganic materials 0.000 description 5
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 5
- 239000000575 pesticide Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- PNVJTZOFSHSLTO-UHFFFAOYSA-N Fenthion Chemical compound COP(=S)(OC)OC1=CC=C(SC)C(C)=C1 PNVJTZOFSHSLTO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- GUVLYNGULCJVDO-UHFFFAOYSA-N EPTC Chemical compound CCCN(CCC)C(=O)SCC GUVLYNGULCJVDO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003899 bactericide agent Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000010721 machine oil Substances 0.000 description 2
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 2
- VOEYXMAFNDNNED-UHFFFAOYSA-N metolcarb Chemical compound CNC(=O)OC1=CC=CC(C)=C1 VOEYXMAFNDNNED-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- QXJKBPAVAHBARF-BETUJISGSA-N procymidone Chemical compound O=C([C@]1(C)C[C@@]1(C1=O)C)N1C1=CC(Cl)=CC(Cl)=C1 QXJKBPAVAHBARF-BETUJISGSA-N 0.000 description 2
- 239000002728 pyrethroid Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 238000002137 ultrasound extraction Methods 0.000 description 2
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 2
- ZCVAOQKBXKSDMS-AQYZNVCMSA-N (+)-trans-allethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-AQYZNVCMSA-N 0.000 description 1
- OVANCIHPSBMNEN-UHFFFAOYSA-N (2,2-dimethyl-3h-1-benzofuran-7-yl)methylcarbamic acid Chemical compound C1=CC(CNC(O)=O)=C2OC(C)(C)CC2=C1 OVANCIHPSBMNEN-UHFFFAOYSA-N 0.000 description 1
- FMTFEIJHMMQUJI-NJAFHUGGSA-N 102130-98-3 Natural products CC=CCC1=C(C)[C@H](CC1=O)OC(=O)[C@@H]1[C@@H](C=C(C)C)C1(C)C FMTFEIJHMMQUJI-NJAFHUGGSA-N 0.000 description 1
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 description 1
- HNMBOGGRDXLHPW-UHFFFAOYSA-N CC(C)C([S+]=P(N)([O-])O)=O Chemical compound CC(C)C([S+]=P(N)([O-])O)=O HNMBOGGRDXLHPW-UHFFFAOYSA-N 0.000 description 1
- DCWFTDIAKJXMOZ-UHFFFAOYSA-N CNC(=O)C=COP(O)(O)=O Chemical compound CNC(=O)C=COP(O)(O)=O DCWFTDIAKJXMOZ-UHFFFAOYSA-N 0.000 description 1
- 239000005947 Dimethoate Substances 0.000 description 1
- FSAVDKDHPDSCTO-WQLSENKSSA-N [(z)-2-chloro-1-(2,4-dichlorophenyl)ethenyl] diethyl phosphate Chemical compound CCOP(=O)(OCC)O\C(=C/Cl)C1=CC=C(Cl)C=C1Cl FSAVDKDHPDSCTO-WQLSENKSSA-N 0.000 description 1
- YASYVMFAVPKPKE-UHFFFAOYSA-N acephate Chemical compound COP(=O)(SC)NC(C)=O YASYVMFAVPKPKE-UHFFFAOYSA-N 0.000 description 1
- 238000003811 acetone extraction Methods 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 description 1
- 229940024113 allethrin Drugs 0.000 description 1
- HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 description 1
- 229940043377 alpha-cyclodextrin Drugs 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- XEGGRYVFLWGFHI-UHFFFAOYSA-N bendiocarb Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)O2 XEGGRYVFLWGFHI-UHFFFAOYSA-N 0.000 description 1
- HKPHPIREJKHECO-UHFFFAOYSA-N butachlor Chemical compound CCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC HKPHPIREJKHECO-UHFFFAOYSA-N 0.000 description 1
- 239000000073 carbamate insecticide Substances 0.000 description 1
- 229960005286 carbaryl Drugs 0.000 description 1
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000004148 curcumin Substances 0.000 description 1
- 229940097362 cyclodextrins Drugs 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- NAGJZTKCGNOGPW-UHFFFAOYSA-K dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [O-]P([O-])([S-])=S NAGJZTKCGNOGPW-UHFFFAOYSA-K 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- KQTVWCSONPJJPE-UHFFFAOYSA-N etridiazole Chemical compound CCOC1=NC(C(Cl)(Cl)Cl)=NS1 KQTVWCSONPJJPE-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- DIRFUJHNVNOBMY-UHFFFAOYSA-N fenobucarb Chemical compound CCC(C)C1=CC=CC=C1OC(=O)NC DIRFUJHNVNOBMY-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- GNDPAVKYAUIVEB-NTEUORMPSA-N furonazide Chemical compound C=1C=COC=1C(/C)=N/NC(=O)C1=CC=NC=C1 GNDPAVKYAUIVEB-NTEUORMPSA-N 0.000 description 1
- 229950001880 furonazide Drugs 0.000 description 1
- 238000010413 gardening Methods 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- QBSJMKIUCUGGNG-UHFFFAOYSA-N isoprocarb Chemical compound CNC(=O)OC1=CC=CC=C1C(C)C QBSJMKIUCUGGNG-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- KRTSDMXIXPKRQR-AATRIKPKSA-N monocrotophos Chemical compound CNC(=O)\C=C(/C)OP(=O)(OC)OC KRTSDMXIXPKRQR-AATRIKPKSA-N 0.000 description 1
- NKUXJZGXSINEMP-UHFFFAOYSA-N n-propan-2-yl-1,3,5-triazin-2-amine Chemical compound CC(C)NC1=NC=NC=N1 NKUXJZGXSINEMP-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- XAMUDJHXFNRLCY-UHFFFAOYSA-N phenthoate Chemical compound CCOC(=O)C(SP(=S)(OC)OC)C1=CC=CC=C1 XAMUDJHXFNRLCY-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- QXJKBPAVAHBARF-UHFFFAOYSA-N procymidone Chemical compound O=C1C2(C)CC2(C)C(=O)N1C1=CC(Cl)=CC(Cl)=C1 QXJKBPAVAHBARF-UHFFFAOYSA-N 0.000 description 1
- PWYIUEFFPNVCMW-UHFFFAOYSA-N propaphos Chemical compound CCCOP(=O)(OCCC)OC1=CC=C(SC)C=C1 PWYIUEFFPNVCMW-UHFFFAOYSA-N 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000008279 sol Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- 238000010977 unit operation Methods 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は２５℃における水溶解度が１０ ｐｐｍ以上や
農薬活性成分にサイクロデキストリンを添加したことを
特徴とする農薬組成物に関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an agrochemical composition characterized by having a water solubility at 25° C. of 10 ppm or more and containing cyclodextrin as an agrochemical active ingredient.
農薬活性成分は、粉剤、水利剤、粉剤、乳剤、ゾル剤、
燻煙剤等、種々の剤型に製剤し、より高い活性を発現し
、残効性に富み、使用者が使用しやすく安全であるよう
に、かつ環境条件の悪化を少なくするようにされている
。また、その製剤が使用時まで安定である必要がある。Pesticide active ingredients include powders, irrigation agents, powders, emulsions, sol preparations,
They are formulated into various dosage forms, such as smoking agents, to express higher activity, have a long residual effect, be easy to use for users, and be safe, while minimizing the deterioration of environmental conditions. There is. Additionally, the formulation must be stable until use.
それらの活性成分が生体上で活性を発現するには、成分
が溶解し、活性点に到達する必要がある。その丸めには
、通常、１Ｎ！解度上昇、付着性上昇の目的で界面活性
剤等の添加が行われている。In order for these active ingredients to exhibit activity on living organisms, they must be dissolved and reach the active site. The rounding is usually 1N! Surfactants and the like are added for the purpose of increasing solubility and adhesion.
近年農薬活性成分をサイクロデキストリンに包接化させ
ることにより解決する手法が提案されている。In recent years, a method has been proposed to solve this problem by clathrating pesticide active ingredients into cyclodextrin.
例えば、特開昭５１−９５１３５号には有機リン系良薬
上β−サイクロデキストリンを包接化させ不快刺戟臭の
減少、特開昭５８−１３４００４号には農薬活性成分と
β−サイクロデキストリンを包接化させ付着性、固層性
の改善、特開昭４９−１３４８４４号、同５９−５！！
４０１号等には農薬活性成分とβ−サイクロデキストリ
ンとの包接化により揮散抑制、特開昭４９−７１１５５
号、同５５−１４９２０３号及び同５５−１４９２０２
号にはピレスロイド系化合物とβ−サイクロデキストリ
ンを包接化させ熱や光に対する安定性を改善し残効性を
向上させる等、種々の目的でβ−サイクロデキス） Ｉ
Ｊンの使用が試みられている。For example, in JP-A No. 51-95135, an organophosphorus drug is included with β-cyclodextrin to reduce unpleasant irritating odor, and in JP-A-58-134004, an agrochemical active ingredient and β-cyclodextrin are included. Improvement of adhesion and solidification by contacting, JP-A-49-134844, JP-A-59-5! !
No. 401, etc., suppresses volatilization by inclusion of agricultural chemical active ingredients and β-cyclodextrin, JP-A-49-71155
No. 55-149203 and No. 55-149202
The number contains β-cyclodextrin (β-cyclodextrin) for various purposes, such as inclusion of pyrethroid compounds and β-cyclodextrin to improve stability against heat and light and increase residual efficacy.
Attempts have been made to use J.
しかしながら従来の技術は、農薬活性成分とβ−サイク
ロデキストリンを包接化させ、その包接体を単離し使用
し、しかも包接化するには農薬活性成分とサイクロデキ
ストリンを単に混合したのみでは包接化は行なわれず、
サイクロデキス） ＩＪンと一定量の水及び農薬活性成
分を混合し、機械的又は熱的な力を加えることにより包
接化が行なわれる。However, the conventional technology involves clathrating the pesticide active ingredient and β-cyclodextrin, and then isolating and using the clathrate. No contact was made;
Inclusion is carried out by mixing IJ (cyclodextrin) with a certain amount of water and an agricultural chemical active ingredient, and applying mechanical or thermal force.
以上の如く包接体を得るには混合、ｒ過、乾燥等の単位
操作を必要とし、包接体濃度とじて農薬活性成分がサイ
クロデキストリンと等モル以下の場合が多く高濃度粉末
が得にくく、又現状ではサイクロデキストリンが高価格
である事等の問題点がある。As mentioned above, in order to obtain the clathrate, unit operations such as mixing, filtration, and drying are required, and the concentration of the clathrate is often less than the equimolar amount of the pesticide active ingredient as the cyclodextrin, making it difficult to obtain a highly concentrated powder. Also, there are currently problems such as the high cost of cyclodextrin.
本発明者等はこれらの課題を解決すべく鋭意研究を重ね
た結果、農薬活性成分１重量部に対してサイクロデキス
トリン１１′−１１０重量部を配合することにより包接
体を調製したと同様の水溶解度上昇、揮散性抑制、光に
対する安定性が改善され、生物活性の上昇及び残効性の
改善がはかられることをみいだして本発明を完成させた
。As a result of extensive research to solve these problems, the present inventors have found that a similar clathrate was prepared by blending 11'-110 parts by weight of cyclodextrin with 1 part by weight of the agricultural chemical active ingredient. The present invention was completed by discovering that water solubility is increased, volatility is suppressed, stability against light is improved, biological activity is increased, and residual effectiveness is improved.
本発明は製剤中では何ら包接化されておらず、単にサイ
クロデキス） ＩＪンは担体の一部にすぎない。サイク
ロデキストリンと農薬活性成分の配合割合において、サ
イクロデキストリンは有効成分の水溶解度の程度に応じ
て存在していれば良く、通常は農薬活性成分を完全に包
接化させるに必要な量より少なくて良い。In the present invention, there is no inclusion in the preparation, and the cyclodextrin is merely a part of the carrier. Regarding the blending ratio of cyclodextrin and agrochemical active ingredient, it is sufficient that the cyclodextrin is present depending on the degree of water solubility of the active ingredient, and usually the amount is less than that required to completely clathrate the agrochemical active ingredient. good.
本発明の農薬組成物は檎々の剤型により使用され、環境
中の水等により包接化が行なわれ所期の目的を達するも
のである。The agrochemical composition of the present invention is used in the desired dosage form and is clathrated with water in the environment to achieve the intended purpose.
本発明で使用できる農薬活性成分としては、２５℃にお
ける水溶解度が１０ ｐｐｍ以上であれば良く、例えば
下記に示す農薬活性成分を例示することができる。The agrochemical active ingredient that can be used in the present invention may have a water solubility of 10 ppm or more at 25°C, and examples thereof include the agrochemical active ingredients shown below.
殺虫剤として
０．０−ジエチル ５−２−エチルチオエチル ホスホ
ロジチオエート（−役名エチルチオメトン）、０，０−
ジメチル Ｓ−フタルイミドメチル ホスホロジチオエ
ート（−役名ＰＭＰ）、Ｓ−２，５−ジヒドロ−５−メ
トキシ−２−オキソ−１，３，４−チアジアゾル−５−
イルメチル０，０−ジメチルホスホロジチオニー ト（
−役名ＤＭＴＰ）、０．Ｓ−ジメチルアセチルホスホロ
アミドチオエート（−役名アセフヱート）、２−クロロ
−１−（２，４−ジクロロフェニル）ビニルジエチルホ
スフェ−）（−ｆｆ名ｃＶＰ）、Ｑ−４−シフ／フェニ
ル０−エチルフェニルホスホノチオエート（−役名ＣＹ
Ｐ）、０．Ｏ−ジエチル０−２−イソプロピル−６−メ
チルピリミジン−４−イルホスホロチオエート（−役名
ダイアジノン）、Ｏ，ｏ−ジメチル０−４−メチルチオ
−ｍ−トリルホスホロチオエート（−役名ＭＰＰ）、Ｓ
−１，２−ビス（エトキシカルボニル）エチル０，０−
ジメチルホスホロジチオエート（−役名マラソン）、Ｓ
−α−エトキシカルボニルベンジルｏ、ｏ−ジメチルホ
スホロジチオエート（−役名ＰＡＰ）、４−（メチルチ
オ）フヱニル ジプロピルホスフェート（−役名プロバ
ホス）、Ｓ−４，６−ジアミツー１，５゜５−トリアジ
ン−２−イルメチル０，０−ジメチルホスホロジチオエ
ート（−役名メナゾン）、２−メトキシ−４Ｈ−ベンゾ
−１，５，２−ジオキサホスホリン２−サルファイド（
−役名すリ千オン）、ジメチル（Ｄ−１−メチル−２−
（メチルカルバモイル）ビニルホスフェ−）（−ｆｆ名
モノクロトホス）、０．０−ジメチルＳ−メチルカルバ
モイルメチル ホスホロジチオエート（−役名ジメトエ
ート）等の有機リン系殺虫剤、ｍ−）リルメチルカーパ
メート（−役名ＭＴＭＣ）、２−イソプロピルフェニル
メチルカーバメート（−役名ＭＩ ＰＣ）、３，４−キ
シリルメチルカーバメート（−役名ＭＰＭＣ）、 ２−
５ｅｃ−プチルフェニルメチルカーバメー） （−役名
ＢＰＭＣ）、１−ナフチルメチルカーバメート（−役名
ＮＡＣ）、２−インプロポキシフヱニル メチルカーバ
メート（−役名ＰＨＣ）、２，２−ジメチル−１，３−
ベンゾジオキソール−４−イルメチルカーバメート（−
役名ペンジオカルブ）、２，３−ジヒドロ−２，２−ジ
メチルベンゾフラン−７−イルメチルカーバメート（−
役名力ルポフラン）等のカーバメート系殺虫剤、（Ｉｎ
３）−３−アリル−２−メチル−４−オキソシクロベン
ト−２−工二ル（Ｉｎ２）−シス−トランス−２，２−
ジメチル−３−（２−メチルプロペ−１−エニル）シク
ロプロバンカーポキシレート（−役名アレスリン）、（
Ｒ８）−α−シアノ−３−フェノキシベンジル（Ｉｎ２
）−シス−トランス−５−（２゜２−ジクロロビニル）
−１，１−ジメチルシクロプロバンカーポキシレート（
−役名サイバーメスリン）等のピレスロイド系殺虫剤。As an insecticide, 0.0-diethyl 5-2-ethylthioethyl phosphorodithioate (- role name: ethylthiometone), 0,0-
Dimethyl S-phthalimidomethyl phosphorodithioate (-position name PMP), S-2,5-dihydro-5-methoxy-2-oxo-1,3,4-thiadiazole-5-
ylmethyl 0,0-dimethylphosphorodithionite (
- role name DMTP), 0. S-dimethylacetylphosphoramidothioate (-role name acephate), 2-chloro-1-(2,4-dichlorophenyl)vinyl diethyl phosphate) (-ff name cVP), Q-4-Schiff/phenyl 0- Ethyl phenylphosphonothioate (-role name CY
P), 0. O-diethyl 0-2-isopropyl-6-methylpyrimidin-4-yl phosphorothioate (- role name diazinon), O,o-dimethyl 0-4-methylthio-m-tolyl phosphorothioate (- role name MPP), S
-1,2-bis(ethoxycarbonyl)ethyl0,0-
Dimethyl phosphorodithioate (- role name Marathon), S
-α-Ethoxycarbonylbenzyl o,o-dimethylphosphorodithioate (-position name PAP), 4-(methylthio)phenyl dipropyl phosphate (-position name probaphos), S-4,6-diamito-1,5゜5-triazine -2-ylmethyl 0,0-dimethylphosphorodithioate (- role name Menazone), 2-methoxy-4H-benzo-1,5,2-dioxaphosphorine 2-sulfide (
- role name Suli Senion), dimethyl (D-1-methyl-2-
Organophosphorus insecticides such as (methylcarbamoyl)vinylphosphate) (-ff name monocrotophos), 0.0-dimethyl S-methylcarbamoylmethyl phosphorodithioate (-functional name dimethoate), m-)lyl methyl carpamate (- role name MTMC), 2-isopropylphenyl methyl carbamate (- role name MI PC), 3,4-xylyl methyl carbamate (- role name MPMC), 2-
5ec-butylphenylmethylcarbamate) (-role name BPMC), 1-naphthylmethylcarbamate (-role name NAC), 2-impropoxyphenyl methylcarbamate (-role name PHC), 2,2-dimethyl-1,3-
Benzodioxol-4-yl methyl carbamate (-
Pendiocarb), 2,3-dihydro-2,2-dimethylbenzofuran-7-ylmethylcarbamate (-
Carbamate insecticides such as Lupofuran), (In
3) -3-Allyl-2-methyl-4-oxocyclobent-2-endyl(In2)-cis-trans-2,2-
Dimethyl-3-(2-methylprop-1-enyl)cycloprobancarpoxylate (-role name allethrin), (
R8)-α-cyano-3-phenoxybenzyl (In2
)-cis-trans-5-(2°2-dichlorovinyl)
-1,1-dimethylcycloproban carpoxylate (
-Pyrethroid insecticides such as Cybermethrin.
殺菌剤としては
５．６−シヒドロー２−メチル−１，４−オキサチイン
−３−カーボキシアニリド（−役名カルボキシン）、５
−エトキシ−３−トリクロロメチル−１，２，４−チア
ジアゾール（−役名工クロメゾール）、１，２，５．６
−チトラハイドロー ４ Ｈ−ピロロ−（Ｒｅ Ｌ ’
−１−Ｊ ） −キノリ７−４−オン（−役名ビロキロ
ン）、メチルベンズイミダゾール−２−イルカ−バメー
ト（−役名力ルベンダゾール）等の殺菌剤。As a bactericidal agent, 5.6-sihydro-2-methyl-1,4-oxathiin-3-carboxyanilide (-character name: carboxin), 5
-Ethoxy-3-trichloromethyl-1,2,4-thiadiazole (-Yakumeko Clomezole), 1,2,5.6
-Chitrahydro 4H-pyrrolo-(Re L'
-1-J) -Bactericidal agents such as -quinolin-7-4-one (-pronounced viloxilon) and methylbenzimidazole-2-ylbamate (-pronounced "rubendazole").
除草剤としては
Ｓ−エチルＮ、Ｎ−へキサメチレンチオカーバメート（
−役名モリネート）、Ｓ−エチルジプロピル（チオカー
バメート）（−役名ＥＰＴＣ）、２−クロロ−２ｚ／−
ジエチル−Ｎ−メトキシメチルアセトアニリド（−役名
アラクロール）、Ｎ−ブトキシメチル−２−クロロ−７
，／−ジエチルアセトアニリド（−役名ブタクロール）
、３−イソプロピル（１Ｈ）−２，１，Ｓ −ベンゾチ
アジン−４（ＡＨ）−オン２，２−ジオキサイド（−役
名ヘンタゾン）、２−１０ロー４−エチルアミノ−６−
イソプロビルアミノ−１，３，５−トリアジン（−役名
アドラジン）等の除草剤。As a herbicide, S-ethyl N, N-hexamethylene thiocarbamate (
- role name molinate), S-ethyldipropyl (thiocarbamate) (- role name EPTC), 2-chloro-2z/-
Diethyl-N-methoxymethylacetanilide (-character name alachlor), N-butoxymethyl-2-chloro-7
,/-diethylacetanilide (-role name butachlor)
, 3-isopropyl(1H)-2,1,S-benzothiazin-4(AH)-one 2,2-dioxide (-role name hentazone), 2-10rho 4-ethylamino-6-
Herbicides such as isopropylamino-1,3,5-triazine (-adrazine).
本発明で使用できるサイクロデキストリンとしては例え
ばα−サイクロデキストリン、β−サイクロデキストリ
ン、ｒ−サイクロデキストリン、メチルサイクロデキス
トリン、エチルサイクロデキストリン、ジメチルサイク
ロデキストリン、ヒドロキシプロピルサイクロデキスト
リン等を挙げることができる。Examples of the cyclodextrin that can be used in the present invention include α-cyclodextrin, β-cyclodextrin, r-cyclodextrin, methylcyclodextrin, ethylcyclodextrin, dimethylcyclodextrin, hydroxypropylcyclodextrin, and the like.
これらのサイクロデキストリンは単独で又は混合して使
用することができる。These cyclodextrins can be used alone or in combination.
サイクロデキストリンの配合割合は農薬活性成分１重量
部に対してα１乃至２０重量部の範囲から適宜選択すれ
ば良い。The blending ratio of cyclodextrin may be appropriately selected from the range α1 to 20 parts by weight per 1 part by weight of the agrochemical active ingredient.
本発明の農薬組成物は農薬製剤上の言渋に従って粉剤、
粉剤、水利剤、顆粒水利剤、懸濁剤、フローダスト又は
燻煙剤等の剤型に調整することができる。The agrochemical composition of the present invention is a powder,
It can be adjusted to a dosage form such as a powder, an irrigation agent, a granular irrigation agent, a suspension, a flow dust, or a smoke agent.
以下に本発明の実施例及び試験例を示すが本発明はこれ
らに限定されるものではない。Examples and test examples of the present invention are shown below, but the present invention is not limited thereto.
面部とあるのは重量部を示す。"Area part" indicates a part by weight.
実施例１
ＭＴＭＣ（−役名） ２５部β−
サイクロデキストリン ５部ＮＰＥ
−１ｏｏ （第−工業製薬製） ２部リグニン
スルホン酸カルシウム ４部含水珪酸（ト
クシールＮ、徳山曹達製） ２５部クレー
３９部以上をリボンブレンダー
で混合し、ジェットマイザーで粉砕し水利剤とする。Example 1 MTMC (- role name) 25 copies β-
Cyclodextrin 5 parts NPE
-1oo (manufactured by Dai-Kogyo Seiyaku) 2 parts calcium lignin sulfonate 4 parts hydrated silicic acid (Tokusil N, manufactured by Tokuyama Soda) 25 parts clay
Mix at least 39 parts with a ribbon blender and crush with a jet miser to make an irrigation agent.
実施例２
ＤＭＴＰ（−役名） ３６部β−
サイクロデキストリン ５６！ｆＩｌハ
イテノ一ル階８（第−工業製薬製） ２部リグニ
ンスルホン酸カルシウム ４部含水珪酸（
トクシールＮ） ２２部以上をリボンブ
レンダーで混合し、ジェットマイザーで粉砕し水利剤と
する。Example 2 DMTP (- role name) 36 parts β-
Cyclodextrin 56! fIl High Tenol 8 (manufactured by Dai-Kogyo Seiyaku) 2 parts calcium ligninsulfonate 4 parts hydrated silicic acid (
Tokusil N) Mix 22 parts or more with a ribbon blender and crush with a jet miser to make an irrigation agent.
実施例３
ＮＡＣ（−役名） ３６部β−サイク
ロデキストリン ２５部５Ｐ−５０２９
（東邦化学展） Ｓ部デモールＴ（花王
アトラス製） ２部クレー
２０部以上をリボンブレンダーで混合し
、スーパーミクロンミル（細組ミクロン製）で粉砕し水
利剤とする。Example 3 NAC (-role name) 36 parts β-cyclodextrin 25 parts 5P-5029
(Toho Chemical Exhibition) S part Demol T (manufactured by Kao Atlas) 2 parts clay
Mix 20 parts or more with a ribbon blender and grind with a Super Micron Mill (manufactured by Hosogumi Micron) to make an irrigation agent.
実施例４
ＢＰＭｃ（−役名） ２５部β
−サイクロデキストリン ２５部ＰＡ
Ｐ（イソプロピルリン酸） １３部含
水珪酸（トクシールＮ） ２部炭
酸カルシウム ３０部り、
４０．２部以上をリボン
ブレンダーで混合し、自由粉砕機（奈良機械製）で粉砕
し粉剤とする。Example 4 BPMc (- role name) 25 copies β
-Cyclodextrin 25 parts PA
P (isopropyl phosphoric acid) 13 parts hydrated silicic acid (Toxil N) 2 parts calcium carbonate 30 parts,
40.2 parts or more were mixed using a ribbon blender and ground using a free grinder (manufactured by Nara Kikai) to form a powder.
実施例５
ＰＭＰ（−役名） ３部β
−サイクロデキストリン １５部ＰＡ
Ｐ （インプロピルリン酸）０．３部含水珪酸（トクシ
ールＮ） ｓ部クレー
７１７部以上をリボンブレンダーで混合し
自由粉砕機で粉砕し粉剤とする。Example 5 PMP (- role name) 3 part β
-Cyclodextrin 15 parts PA
P (inpropyl phosphoric acid) 0.3 parts hydrated silicic acid (Toxil N) s part clay
At least 717 parts were mixed in a ribbon blender and ground in a free grinder to form a powder.
実施例６
ＭＰＰ（−役名） ３部β
−サイクロデキストリン ６部ＰＡ
Ｐ（イソプロピルリン酸）Ｑ、３部含水珪酸（トクシー
ルＮ） ｓ部クレー
８７．７部以上をリボンブレンダーで
混合し自由粉砕機で粉砕し粉剤とする。Example 6 MPP (- role name) 3 part β
-Cyclodextrin 6-part PA
P (isopropyl phosphoric acid) Q, 3 parts hydrated silicic acid (Toxil N) s part clay
87.7 parts or more were mixed in a ribbon blender and ground in a free grinder to form a powder.
実施例７
ダイアジノン（−役名） ５ 部
ＧＡＮ（日本化薬製） １４５
部リアクトＣＡ１０１ （三洋化成製）
（１４５部以上の混合液を炭酸カルシウム粉砕粉（１４
〜３２メツシユ） ９（Ｌ６ 部にセメントミキサー
でインプレし均一とした後、β−サイクロデキス） Ｉ
Ｊン２．５部及び含水珪酸１部を混合した粉末を加えコ
ーティングして粒剤とする。Example 7 Diazinon (-role name) 5 part GAN (manufactured by Nippon Kayaku) 145
Part React CA101 (manufactured by Sanyo Chemical)
(Add 145 parts or more of the mixed solution to pulverized calcium carbonate powder (14 parts or more)
~32 meshes) 9 (After impregnating the L6 part with a cement mixer and making it uniform, β-cyclodextrin) I
A powder mixture of 2.5 parts of silicic acid and 1 part of hydrated silicic acid is added and coated to form granules.
実施例８
ＰＡＰ（−役名） ２０部β
−サイクロデキストリン ４０部含水
珪酸 １０部タルク
２２部ハイテノールＮｌ１Ｂ
５部リグニンスルホン酸カルシウ
ム ３部以上をリボンブレンダーで混合
し、自由粉砕機で粉砕後、アレキサンダー式乾式造粒機
０印−５０型ターボ工業製）で造粒し、１４Ｓ５２メツ
シユの航空散布用顆粒水利剤とする。Example 8 PAP (- role name) 20 copies β
-Cyclodextrin 40 parts Hydrous silicic acid 10 parts Talc
22 parts hightenol Nl1B
5 parts Calcium ligninsulfonate 3 parts or more are mixed in a ribbon blender, pulverized in a free pulverizer, and granulated in an Alexander type dry granulator 0 mark-50 (manufactured by Turbo Kogyo) to produce 14S52 mesh granules for aerial spraying. Use as an irrigation agent.
実施例９
ＤＭＴＰ（−役名） １５部β
−サイクロデキストリン １５部含水珪
酸 ６９．７部ＰＡＰ
（イソプロピルリン酸） （１３部以
上をリボンブレンダーで混合し、ジェットミルで粉砕し
てハウス園芸用フローダスト剤とする。Example 9 DMTP (- role name) 15 parts β
-Cyclodextrin 15 parts Hydrous silicic acid 69.7 parts PAP
(Isopropyl phosphoric acid) (Mix 13 parts or more with a ribbon blender and grind with a jet mill to make a flow dust agent for greenhouse gardening.
実施例１０
カルボキシン（−役名） １０部β
−サイクロデキストリン １０部農薬
用マシン油 ５５部メチル
ナフタレン ５部白灯油
１５部
ノイゲンＥＴ−１２０（第−工業裏薬製） ５部以
上を回転数１７００ｒｐｎｌのサンドグライダ−（五十
嵐機械製）で２時間湿式粉砕して、オイルベースの懸濁
剤とする。Example 10 Carboxin (-role name) 10 parts β
- Cyclodextrin 10 parts Machine oil for pesticides 55 parts Methylnaphthalene 5 parts White kerosene 15 parts Neugen ET-120 (manufactured by Dai-Kogyo Urayaku) 5 parts or more were mixed with a sand glider (manufactured by Igarashi Kikai) with a rotation speed of 1700 rpm for 2 hours. Wet grind into an oil-based suspension.
比較例１
実施例１のβ−サイクロデキス） ＩＪンにかえてクレ
ーを４４部とじ水利剤とする。Comparative Example 1 44 parts of clay was added instead of the β-cyclodextrin of Example 1 to prepare an irrigation agent.
比較例２
実施例２のβ−サイクロデキストリンにかえて含水珪酸
（トクシールＮ〕を５８部用いて、水和剤とする。Comparative Example 2 A hydrating agent was prepared by using 58 parts of hydrated silicic acid (Toxil N) in place of β-cyclodextrin in Example 2.
比較例３
実施例Ｓのβ−サイクロデキストリンにかえてクレーを
４５部とし、水利剤とする。Comparative Example 3 45 parts of clay was used in place of β-cyclodextrin in Example S to prepare an irrigation agent.
比較例４
実施例４のβ−サイクロデキストリンにかえてクレーを
６５．２部とし、粉剤とする。Comparative Example 4 In place of β-cyclodextrin in Example 4, 65.2 parts of clay was used to prepare a powder.
比較例５
実施例５のβ−サイクロデキストリンにかえてクレーを
９３．７９とし、粉剤とする。Comparative Example 5 The β-cyclodextrin of Example 5 was replaced with clay having a concentration of 93.79, and a powder was prepared.
比較例６
実施例６のβ−サイクロデキスト９７番こかえてクレー
を９五７部とし、粉剤とする。Comparative Example 6 957 parts of clay was added to β-cyclodext No. 97 of Example 6 to prepare a powder.
比較例７
実施例７のβ−サイクロデキストリンにかえて炭酸カル
シウム粉末２．５部を使用し粒剤とした。Comparative Example 7 In place of β-cyclodextrin in Example 7, 2.5 parts of calcium carbonate powder was used to prepare granules.
比較例８
実施例８のβ−サイクロデキストリンにかえてタルクを
６２部とじ航窒散布用水利剤とする。Comparative Example 8 In place of β-cyclodextrin in Example 8, 62 parts of talc was added to prepare an irrigation agent for spraying nitrogen.
比較例９
実施例９のβ−サイクロデキストリンにかえて含水珪酸
を８４．７部としハウス園芸用フローダスト剤とする。Comparative Example 9 In place of β-cyclodextrin in Example 9, 84.7 parts of hydrated silicic acid was used to prepare a flow dust agent for greenhouse horticulture.
比較例１０
実施例１０のβ−サイクロデキストリンにかえて農薬用
マシン油を６５部とし、オイルベースの懸濁剤とする。Comparative Example 10 In place of β-cyclodextrin in Example 10, 65 parts of agricultural machine oil was used to prepare an oil-based suspending agent.
比較例１１
キャブタン（−役名）（１１４０部
β−サイクロデキストリン ４０部ＮＰ
Ｅ−１００１部
リグニンスルホン酸カルシウム ３ｓ炭
酸カルシウム １６部以上をリボンブ
レンダーで均一に混合し自由粉砕機で粉砕し水利剤とす
る。Comparative Example 11 Cabtan (- role name) (1140 parts β-cyclodextrin 40 parts NP
E-100 1 part Calcium lignin sulfonate 3s Calcium carbonate 16 parts or more are mixed uniformly with a ribbon blender and crushed with a free crusher to obtain an irrigation agent.
比較例１２
比較例１１のβ−サイクロデキストリンにかえて炭酸カ
ルシウムを５６部とし、水利剤とするＯ
比較例１３
フサライド（−役名）（２） ｓｏ部β−サ
イクロデキストリン ２５部ＮＰＥ−
１００２部
デモールＴ ３部クレー
２０部以上をリボンブレンダー
で均一に混合し、ジェットマイザーで粉砕し、水利剤と
する。Comparative Example 12 56 parts of calcium carbonate was used in place of β-cyclodextrin in Comparative Example 11 to make an irrigation agent. Comparative Example 13 Fusaride (- role name) (2) so part β-cyclodextrin 25 parts NPE-
1002 parts Demol T 3 parts Clay
Mix at least 20 parts uniformly with a ribbon blender and crush with a jet miser to make an irrigation agent.
比較例１４
比較例１３のβ−サイクロデキストリンにかえてクレー
を４５部とじ水利剤とする。Comparative Example 14 In place of β-cyclodextrin in Comparative Example 13, 45 parts of clay was added to prepare an irrigation agent.
比較例１５
プロミドン（−役名）（３） ５．）部
β−サイクロデキストリン ２５部５
Ｐ−５０２９３部
リグニンスルホン酸カルシウム ２部ラ
ジオライト５ｚｏｏ（昭和化学製） ２０部以上
−Ｐ ＩＪポンプレンダ−で混合し、ジェットマイザー
で粉砕し水和剤とする。Comparative Example 15 Promidone (-role name) (3) 5. ) part β-cyclodextrin 25 parts 5
P-5029 3 parts Calcium lignin sulfonate 2 parts Radiolite 5zoo (manufactured by Showa Kagaku) 20 parts or more - P Mix with an IJ pump blender and crush with a jet mister to prepare a wettable powder.
注（１） キャブタン（−役名）；１．２．５． ６
−チトラハイドローＮ−（）ジクロロメチルチオ）フタ
ルイミド。Note (1) Cabtan (- role name); 1.2.5. 6
-Titrahydro N-()dichloromethylthio)phthalimide.
（２） フサライド（−役名）；’ｐ ５ｔ ’ｅ
７−チトラクロロフタリド
（３） プロシミドン（−役名）；Ｎ−（３，５−ジ
クロロフェニル）−１，２−ジメチルシクロプロパン−
１，２−ジカルボキシイミド
試験例１ 製剤中での農薬活性成分とサイクロデキスト
リンの状態
本発明実施例１乃至１０より得られた製剤及び各実施例
の農薬活性成分とサイクロデキストリンの飽和水溶液法
による包接体（活性成分として１ｏｏｍｔ）にアセトン
１０ｍ１ を加え１超音波抽出し、上澄液をＧＬＣ（ガ
スクロマトグラフィー）又はＨＰＬＣ（高速液体クロマ
トグラフィー）で回収率を求めた。その結果を第１表に
示すＯ
第 １ 表
実施例１乃至１０の製剤のアセトン抽出回収率はほぼ１
００％である。それに比べ飽和水溶液法で調製した完全
な包接体は若干アセトンで抽出されるが大半が抽出され
ない。このことは、実施例−１〜１０の製剤中ではβ−
サイクロデキストリンは単なるキャリヤーにすぎず包接
体は形成されてないことを示す。(2) Fusaride (-role name);'p 5t 'e
7-Titrachlorophthalide (3) Procymidone (-role name); N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-
1,2-Dicarboximide Test Example 1 Condition of agricultural chemical active ingredient and cyclodextrin in the formulation By saturated aqueous solution method of the formulations obtained from Examples 1 to 10 of the present invention and the agricultural chemical active ingredient and cyclodextrin of each example 10 ml of acetone was added to the clathrate (1 oomt as active ingredient) and subjected to ultrasonic extraction, and the recovery rate of the supernatant was determined by GLC (gas chromatography) or HPLC (high performance liquid chromatography). The results are shown in Table 1. Table 1 The acetone extraction recovery rates of the formulations of Examples 1 to 10 are approximately 1.
00%. In comparison, complete clathrates prepared by the saturated aqueous solution method are slightly extracted with acetone, but most are not. This means that in the formulations of Examples-1 to 10, β-
This shows that cyclodextrin is just a carrier and no clathrate is formed.
試験例２ 揮散性比較試験
本発明実施例及び比較例で得られる水利剤、顆粒水利剤
、懸濁剤は活性成分として１ｏｏｐｐｍとなるように水
で希釈し、希釈液１ ｍｌを直径９工のシャーレに均一
に塗布する。粉剤及び粒剤は活性成分として１００μｔ
になる量を水２ｒｎｌｌで湿らせた陽２Ｐ紙を敷いた
直径９ｃ１１のシャーレに均一に散布する。Test Example 2 Volatility Comparison Test The irrigation agents, granular irrigation agents, and suspension agents obtained in the Examples and Comparative Examples of the present invention were diluted with water to a concentration of 10ppm as the active ingredient, and 1 ml of the diluted solution was poured into a tube with a diameter of 9 mm. Apply evenly to the petri dish. Powders and granules contain 100μt as active ingredient
Spread the amount evenly on a Petri dish with a diameter of 9cm lined with positive 2P paper moistened with 2ml of water.
各シャーレを風乾後４０℃恒温器に保存し、所定日に取
り出してメタノール１０ｍｌを加え超音波抽出し、ＧＬ
Ｃ又はＨＰＬＣで残存率を求めた。After air-drying each petri dish, store it in a 40℃ incubator, take it out on the specified day, add 10ml of methanol, perform ultrasonic extraction, and GL
The residual rate was determined by C or HPLC.
結果を第２表に示す。The results are shown in Table 2.
第 ２ 表
比較例１１．１５及び１５で使用する活性成分の２５℃
に３ける水溶解度を以下に示す。Table 2 Comparative Examples 11.25°C of the active ingredients used in 15 and 15
The water solubility in 3 is shown below.
キャブタン（−役名）＜［１５ｐｐｍ
フサライド（−役名） ２．４９ｐｐｍプロシミ
ドン（−役名） ムｓ ｐｐｍ第２表に示す
如く、本発明のサイクロデキストリンを添加した製剤は
、顕著に活性成分の揮散を抑制している。又２５℃にお
ける水ａｍ度が１０ ｐｐｍ以下の活性成分では、サイ
クロデキストリンを添加しても揮散抑制効果はみられな
いＯ
試験例５ 水溶解度試験
実施例１乃至１０及び比較例１乃至１６で得られた製剤
について、各々の活性成分の文献記載の水溶解度の１０
濃度となるように水で希釈し、２５℃で１日放置する。Cabtane (- role name) < [15 ppm Fusaride (- role name) 2.49 ppm Procymidone (- role name) Mus ppm As shown in Table 2, the formulation containing the cyclodextrin of the present invention significantly suppresses the volatilization of the active ingredient. are doing. In addition, for active ingredients with a water am content of 10 ppm or less at 25°C, no volatilization suppressing effect is observed even when cyclodextrin is added. 10 of the literature-described aqueous solubility of each active ingredient for the formulated formulations.
Dilute with water to the desired concentration and leave at 25°C for 1 day.
放置後上溌液１０ｄを液体クロマトディスク１３ＣＲ（
ゲルマンサイエンス社製）で濾過し、ｅ液にシクロメタ
ン１０ｍ１を加え抽出し、濃縮後ＧＬＣで溶解度を求め
た結果を第３表に示す。After standing, 10d of the supernatant liquid was transferred to a liquid chromato disk 13CR (
(manufactured by Gelman Science), 10 ml of cyclomethane was added to the e solution for extraction, and after concentration, the solubility was determined by GLC. Table 3 shows the results.
Claims (4)
活性成分にサイクロデキストリンを添加したことを特徴
とする農薬組成物。(1) An agrochemical composition characterized in that cyclodextrin is added to an agrochemical active ingredient having a water solubility of 10 ppm or more at 25°C.
ンである特許請求の範囲第１項記載の農薬組成物。(2) The agricultural chemical composition according to claim 1, wherein the cyclodextrin is β-cyclodextrin.
対し０．１〜２０重量部の割合で添加したことを特徴と
する特許請求の範囲第１又は２項記載の農薬組成物。(3) The agrochemical composition according to claim 1 or 2, characterized in that cyclodextrin is added at a ratio of 0.1 to 20 parts by weight per 1 part by weight of the agrochemical active ingredient.
剤、フローダスト又は燻煙剤である特許請求の範囲第１
項乃至第３項のいずれか１項記載の農薬組成物。(4) Claim 1, in which the composition is a powder, granule, wettable powder, wettable powder, suspension, flow dust, or smoking agent.
The agricultural chemical composition according to any one of Items 1 to 3.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22542486A JPS6379802A (en) | 1986-09-24 | 1986-09-24 | Agricultural chemical composition containing cyclodextrin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22542486A JPS6379802A (en) | 1986-09-24 | 1986-09-24 | Agricultural chemical composition containing cyclodextrin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6379802A true JPS6379802A (en) | 1988-04-09 |
Family
ID=16829154
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22542486A Pending JPS6379802A (en) | 1986-09-24 | 1986-09-24 | Agricultural chemical composition containing cyclodextrin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6379802A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5116825A (en) * | 1989-05-29 | 1992-05-26 | Roquette Freres | Phytosanitary composition, its process for preparation and its use for treating cryptogamic diseases |
| FR2677221A1 (en) * | 1991-06-10 | 1992-12-11 | Roquette Freres | Plant-protection composition, process for preparing it and its use, in particular for controlling weeds |
| AU657818B2 (en) * | 1992-11-25 | 1995-03-23 | Roquette Freres | Plant protection composition, process for its preparation and its use, in particular for controlling weeds |
| US5756484A (en) * | 1995-06-08 | 1998-05-26 | Roquette Freres | Pulverulent hydroxypropyl-β-cyclodextrin composition and process for its preparation |
| WO1999011596A1 (en) * | 1997-08-29 | 1999-03-11 | Meiji Seika Kaisha, Ltd. | Agricultural or horticultural preparation with light stability |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6233103A (en) * | 1985-08-07 | 1987-02-13 | Sankyo Co Ltd | Stable agricultural chemical composition |
| JPS62501771A (en) * | 1985-01-07 | 1987-07-16 | キノイン ギオギスゼル エス ベギエスゼチ テクメチク ギヤラ ア−ルテイ− | How to enhance the activity of plant protection agents by using cyclodextrins |
-
1986
- 1986-09-24 JP JP22542486A patent/JPS6379802A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62501771A (en) * | 1985-01-07 | 1987-07-16 | キノイン ギオギスゼル エス ベギエスゼチ テクメチク ギヤラ ア−ルテイ− | How to enhance the activity of plant protection agents by using cyclodextrins |
| JPS6233103A (en) * | 1985-08-07 | 1987-02-13 | Sankyo Co Ltd | Stable agricultural chemical composition |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5116825A (en) * | 1989-05-29 | 1992-05-26 | Roquette Freres | Phytosanitary composition, its process for preparation and its use for treating cryptogamic diseases |
| AU631850B2 (en) * | 1989-05-29 | 1992-12-10 | Roquette Freres | Phytosanitary composition, its process of preparation and its use for treating cryptogamic diseases |
| FR2677221A1 (en) * | 1991-06-10 | 1992-12-11 | Roquette Freres | Plant-protection composition, process for preparing it and its use, in particular for controlling weeds |
| AU657818B2 (en) * | 1992-11-25 | 1995-03-23 | Roquette Freres | Plant protection composition, process for its preparation and its use, in particular for controlling weeds |
| US5756484A (en) * | 1995-06-08 | 1998-05-26 | Roquette Freres | Pulverulent hydroxypropyl-β-cyclodextrin composition and process for its preparation |
| WO1999011596A1 (en) * | 1997-08-29 | 1999-03-11 | Meiji Seika Kaisha, Ltd. | Agricultural or horticultural preparation with light stability |
| US6242383B1 (en) * | 1997-08-29 | 2001-06-05 | Meiji Seika Kaisha, Ltd. | Agricultural or horticultural preparation with light stability |
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