JPS6361281B2 - - Google Patents
Info
- Publication number
- JPS6361281B2 JPS6361281B2 JP59161024A JP16102484A JPS6361281B2 JP S6361281 B2 JPS6361281 B2 JP S6361281B2 JP 59161024 A JP59161024 A JP 59161024A JP 16102484 A JP16102484 A JP 16102484A JP S6361281 B2 JPS6361281 B2 JP S6361281B2
- Authority
- JP
- Japan
- Prior art keywords
- emulsion
- polyoxyethylene
- phenyl
- ether
- present
- 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.)
- Expired
Links
- 239000000839 emulsion Substances 0.000 claims description 29
- 239000003905 agrochemical Substances 0.000 claims description 11
- 230000001804 emulsifying effect Effects 0.000 claims description 9
- 238000003860 storage Methods 0.000 claims description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
- 239000000575 pesticide Substances 0.000 claims description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000005504 styryl group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- -1 naphtha Chemical compound 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 10
- 238000001556 precipitation Methods 0.000 description 10
- 239000013078 crystal Substances 0.000 description 8
- 239000003995 emulsifying agent Substances 0.000 description 8
- 239000003945 anionic surfactant Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 6
- 238000009472 formulation Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002736 nonionic surfactant Substances 0.000 description 5
- 239000004359 castor oil Substances 0.000 description 4
- 235000019438 castor oil Nutrition 0.000 description 4
- 238000004040 coloring Methods 0.000 description 4
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- ZNOLGFHPUIJIMJ-UHFFFAOYSA-N fenitrothion Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C(C)=C1 ZNOLGFHPUIJIMJ-UHFFFAOYSA-N 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- SCKHCCSZFPSHGR-UHFFFAOYSA-N cyanophos Chemical compound COP(=S)(OC)OC1=CC=C(C#N)C=C1 SCKHCCSZFPSHGR-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 229940088679 drug related substance Drugs 0.000 description 2
- GSGDTSDELPUTKU-UHFFFAOYSA-N nonoxybenzene Chemical compound CCCCCCCCCOC1=CC=CC=C1 GSGDTSDELPUTKU-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- SBNFWQZLDJGRLK-RTWAWAEBSA-N (1R)-trans-phenothrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 SBNFWQZLDJGRLK-RTWAWAEBSA-N 0.000 description 1
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- VTONZKDPQTYHLV-UHFFFAOYSA-N (3-methylphenyl) carbamate Chemical compound CC1=CC=CC(OC(N)=O)=C1 VTONZKDPQTYHLV-UHFFFAOYSA-N 0.000 description 1
- TVFWYUWNQVRQRG-UHFFFAOYSA-N 2,3,4-tris(2-phenylethenyl)phenol Chemical compound C=1C=CC=CC=1C=CC1=C(C=CC=2C=CC=CC=2)C(O)=CC=C1C=CC1=CC=CC=C1 TVFWYUWNQVRQRG-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- CWWMLCAWYADJOM-UHFFFAOYSA-N 6-chloro-3-(diethoxyphosphorylsulfanylmethyl)-1,3-benzoxazol-2-one Chemical compound C1=C(Cl)C=C2OC(=O)N(CSP(=O)(OCC)OCC)C2=C1 CWWMLCAWYADJOM-UHFFFAOYSA-N 0.000 description 1
- OINRITJYJJEHRI-UHFFFAOYSA-N CCOC(C(C(C)(C)[S+]=P([O-])(O)S)C(OCC)=O)=O Chemical compound CCOC(C(C(C)(C)[S+]=P([O-])(O)S)C(OCC)=O)=O OINRITJYJJEHRI-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 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
- PNVJTZOFSHSLTO-UHFFFAOYSA-N Fenthion Chemical compound COP(=S)(OC)OC1=CC=C(SC)C(C)=C1 PNVJTZOFSHSLTO-UHFFFAOYSA-N 0.000 description 1
- 239000005949 Malathion Substances 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- VQXSOUPNOZTNAI-UHFFFAOYSA-N Pyrethrin I Natural products CC(=CC1CC1C(=O)OC2CC(=O)C(=C2C)CC=C/C=C)C VQXSOUPNOZTNAI-UHFFFAOYSA-N 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- JXSJBGJIGXNWCI-UHFFFAOYSA-N diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate Chemical compound CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC JXSJBGJIGXNWCI-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 229960000878 docusate sodium Drugs 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- AWZOLILCOUMRDG-UHFFFAOYSA-N edifenphos Chemical compound C=1C=CC=CC=1SP(=O)(OCC)SC1=CC=CC=C1 AWZOLILCOUMRDG-UHFFFAOYSA-N 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229960000453 malathion Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- LLLFASISUZUJEQ-UHFFFAOYSA-N orbencarb Chemical compound CCN(CC)C(=O)SCC1=CC=CC=C1Cl LLLFASISUZUJEQ-UHFFFAOYSA-N 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 1
- 229960000490 permethrin Drugs 0.000 description 1
- 229960003536 phenothrin Drugs 0.000 description 1
- IOUNQDKNJZEDEP-UHFFFAOYSA-N phosalone Chemical compound C1=C(Cl)C=C2OC(=O)N(CSP(=S)(OCC)OCC)C2=C1 IOUNQDKNJZEDEP-UHFFFAOYSA-N 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 1
- VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical compound CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VJFUPGQZSXIULQ-XIGJTORUSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 229940114926 stearate Drugs 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
農薬乳剤は一般に水に難溶の農薬成分（有効成
分）をキシレン、ナフサ、メタノール、ケロシン
等の有機溶剤に希釈して得た有機溶剤溶液（以下
原液と称する）、この原液を農薬散布時に水に乳
化させるための補助剤即ち乳化剤を加えて調整し
たものである。乳化剤の選定に際しては農薬原体
の化学的、物理的特性を考慮して、乳剤の保存時
に原体の分解や乳剤の外観の変化（着色、結晶の
析出等）を生じさせないことが大切である。
また、乳化剤は散布液を調整する際に用いられ
る希釈水の水質（温度、硬度等）や、薬剤の効力
を高めるための散布液の浸透力、展着力等の物理
性及びエマルジヨンの濃度等を充分に考慮して選
定されるが、乳化剤は通常非イオン性界面活性剤
と陰イオン性界面活性剤とを配合して調整され
る。これ等農薬製剤用の乳化剤として、通常次の
ような化合物が挙げられる。非イオン性界面活性
剤の例としてはポリオキシエチレン〔エチレンオ
キサイドモル数（以下EOと略）４〜20モル〕ノ
ニルフエニルエーテル、ポリオキシエチレン
（EO10〜50モル）キヤスターオイルエーテル、ポ
リオキシエチレン（EO10〜30モル）スチリルフ
エニルエーテル又はこれ等のホルマリン縮合物、
ポリオキシエチレン（EO10〜50モル）ソルビタ
ンアルキレート（ラウレート、ステアレート、オ
レート等）等である。
陰イオン性界面活性剤の例としてはドデシルベ
ンゼンスルホン酸塩（ナトリウム塩、カルシウム
塩および各種アミン塩等）、ジオクチルスルホサ
クシネート（ナトリウム塩、カルシウム塩等）等
が挙げられる。
非イオン性界面活性剤は乳剤の基本的な乳化力
の付与（特にポリオキシエチレンスチリルフエニ
ルエーテル系、ポリオキシエチレンキヤスターオ
イルエーテル系界面活性剤）と乳液の物理性の向
上（特にポリオキシエチレンノニルフエニルエー
テル系界面活性剤）に関与している。
一方、陰イオン性界面活性剤は乳剤の所要
HLBを適切に調節し乳液の安定化に寄与してい
る。
しかし陰イオン性界面活性剤の多用は農薬原体
の分解や乳剤の外観の変化の原因となる場合があ
ることが知られており、このため特に化学的に不
安定な有機りん農薬の乳剤等では安定剤の併用が
行われている。例えば特公昭48−43860号公報、
同55−37967号公報及び特開昭54−98334号公報等
がある。
しかしながら農薬成分によつては乳化剤の選定
だけでは充分な乳化性能が得られない場合が多
く、その解決方法が求められてきた。
本発明者等は農薬乳化剤中に下記一般式で表わ
されるアリル誘導体のエチレンオキサイド又はプ
ロピレンオキサイド附加物を乳剤中に0.5〜５％
添加することにより乳剤保存中における外観の変
化即ち結晶の析出や乳剤表面に発生する“おり”
の生成を防止し、また着色等を防止する効果があ
ること及び農薬のエマルジヨンの安定を強く促進
することを見出して本発明を完成させたものであ
る。
即ち本発明は
一般式
式中、R1は水素原子、フエニル基、スチリル
基を示し、R2は水素原子又はメチル基を示し、
ｎは１〜３の整数、ｍは１又は２の整数を示す。
で表わされるアリル誘導体のエチレンオキサイド
又はプロピレンオキサイド附加物の一種又は二種
以上を乳剤中に0.5〜５％添加することを特徴と
する、乳剤保存中の外観の変化（着色、結晶の析
出等）を防止し且つ乳化性能を向上させた保存性
及び乳化性良好な農薬乳剤の製法に関するもので
ある。
本発明の上記一般式で表わされるアリル誘導体
のエトキシレートとしては例えばフエニルセロソ
ルブ、Ｏ―フエニルフエノールプロポキシレート
（PO2モル）、ジスチリルフエノール―エトキシレ
ート（EO2モル）、トリスチリルフエノールエト
キシレート（EO3モル）などが挙げられるがこれ
等に限定されるものではない。また、本発明に係
る農薬としては有機りん剤；例えば３―ジエトキ
シホスホリルチオメチル―６―クロルベンズオキ
サゾロン（ホサロン）、ジメチルジカルベトキシ
エチルジチオホスフエート（マラチオン）、ジメ
チル―Ｐ―シアノフエニルチオホスフエート（サ
イアノツクス）、ジメチル（３―メチル―４―ニ
トロフエニル）チオホスフエート（フエニトロチ
オン）、Ｏ―Ｏ―ジメチル―Ｏ―〔３―メチル―
４―（メチルチオ）フエニル〕チオフオスフエー
ト（フエンチオン）、Ｏ―エチル―Ｓ，Ｓ―ジフ
エニルジチオフオスフエート（エジフエンホス）、
カーバメート剤；例えば２―セコンダリ―ブチル
フエニル―Ｎ―メチルカーバメート（バツサ）、
１―ナフチル―Ｎ―メチルカーバメート
（NAC）、Ｓ―（２―クロルベンジル）Ｎ，Ｎ―
ジエチルチオカーバメート（オルゾベンカープ）、
３―メトキシカルボニルアミノフエニル―Ｎ―
（3′―メチルフエニル）カーバメート（フエンメ
デイフアム）、ピレスロイド剤；例えばピレスリ
ン、フエノスリン、パーメスリン、フエンバレレ
ート等が挙げられるが、これ等に限定されるもの
ではない。
製剤化に際して使用される乳化剤は通常の農薬
乳剤に使用されるものであり、非イオン性界面活
性剤ではポリオキシエチレン（EO10〜30モル）
スチリル（又はベンジル）フエニル（又はフエニ
ルフエニル）エーテル、ポリオキシエチレン
（EO10〜50モル）キヤスターオイルエーテル、ポ
リオキシエチレン脂肪酸エステル、ポリオキシエ
チレンソルビタンアルキレート等が挙げられる。
陰イオン性界面活性剤としてはドデシルベンゼ
ンスルホン酸カルシウム塩や各種アミン類の塩が
代表的なものとして挙げられる。これ等界面活性
剤が最適の自然乳化性、乳化安定性をもたらすよ
うに配合される。
本発明の化学物質の添加量は乳剤中0.5〜５％
で充分であり、目的に応じて適切な使用率が選ば
れる。又、必要に応じて安定剤との併用も可能で
ある。
本発明の化学物質が結晶析出や“おり”の生成
を防止する機構は明らかではないが非イオン性界
面活性剤と陰イオン性界面活性剤及び農薬原体と
の分子間に介在して相互の親和力溶解力等に影響
を与え、また一部は乳剤表面に配向して原体と陰
イオン性界面活性剤及び空気中の水分等に起因す
る“おり”の発生を防止することが考えられる。
有機りん乳剤中にブチルアルコール、アミルア
ルコール、シクロヘキサノール等のアルコール類
を添加することにより、乳化安定性を向上させる
製法が特公昭46−6438号公報に述べられている
が、一般にかかる低級アルコール類の添加は特に
加水分解しやすく有機りん系の原体に対しては好
ましいものとはいえない。また、かかる乳剤は長
期保存中に着色や沈殿を生ずることが多々認めら
れる。
一方、本発明の物質は構造中にエーテル結合を
有するアリル誘導体のエトキシレートであり、全
く新規の発明といえる。
次に本発明による実施例をあげる。
実施例
結晶の析出、着色の防止効果
下記処方サイアノツクス乳剤を50℃恒温器中に
保存し結晶の析出、着色等の有無を肉眼観察し
た。
Pesticide emulsion is generally an organic solvent solution (hereinafter referred to as stock solution) obtained by diluting a pesticide ingredient (active ingredient) that is poorly soluble in water in an organic solvent such as xylene, naphtha, methanol, or kerosene. It is prepared by adding an auxiliary agent, that is, an emulsifier, to emulsify the liquid. When selecting an emulsifier, it is important to consider the chemical and physical properties of the pesticide active ingredient so that it does not cause decomposition of the active ingredient or change in the appearance of the emulsion (coloring, precipitation of crystals, etc.) during storage of the emulsion. . In addition, emulsifiers are used to adjust the water quality (temperature, hardness, etc.) of the dilution water used when preparing the spray solution, physical properties such as penetration power and spreading power of the spray solution to increase the efficacy of the drug, and concentration of the emulsion. Although the emulsifier is selected with due consideration, it is usually prepared by blending a nonionic surfactant and an anionic surfactant. As emulsifiers for these agricultural chemical formulations, the following compounds are usually mentioned. Examples of nonionic surfactants include polyoxyethylene [4 to 20 moles of ethylene oxide (hereinafter abbreviated as EO)] nonylphenyl ether, polyoxyethylene (10 to 50 moles of EO) castor oil ether, polyoxy Ethylene (EO10-30 mol) styryl phenyl ether or formalin condensate thereof,
These include polyoxyethylene (EO10-50 mol), sorbitan alkylate (laurate, stearate, oleate, etc.). Examples of anionic surfactants include dodecylbenzenesulfonate (sodium salt, calcium salt, various amine salts, etc.), dioctyl sulfosuccinate (sodium salt, calcium salt, etc.), and the like. Nonionic surfactants provide basic emulsifying power to emulsions (especially polyoxyethylene styrylphenyl ether and polyoxyethylene castor oil ether surfactants) and improve the physical properties of emulsions (especially polyoxyethylene castor oil ether surfactants). (ethylene nonyl phenyl ether surfactants). On the other hand, anionic surfactants are required for emulsions.
It appropriately regulates HLB and contributes to the stabilization of emulsion. However, it is known that excessive use of anionic surfactants may cause decomposition of the agricultural chemical substance or change in the appearance of the emulsion. Stabilizers are used in combination. For example, Special Publication No. 48-43860,
There are Japanese Patent Publications No. 55-37967 and Japanese Unexamined Patent Publication No. 54-98334. However, depending on the agricultural chemical component, it is often not possible to obtain sufficient emulsifying performance simply by selecting an emulsifier, and a solution to this problem has been sought. The present inventors added ethylene oxide or propylene oxide adducts of allyl derivatives represented by the following general formula to agricultural chemical emulsifiers in an amount of 0.5 to 5%.
The addition of this additive may cause changes in the appearance of the emulsion during storage, such as precipitation of crystals and "staining" that occurs on the surface of the emulsion.
The present invention was completed based on the discovery that it has the effect of preventing the formation of agrochemicals and discoloration, and that it strongly promotes the stability of emulsions of agricultural chemicals. That is, the present invention has the general formula In the formula, R 1 represents a hydrogen atom, a phenyl group, or a styryl group, and R 2 represents a hydrogen atom or a methyl group,
n represents an integer of 1 to 3, and m represents an integer of 1 or 2. Changes in appearance during storage of emulsion (coloring, precipitation of crystals, etc.) characterized by adding 0.5 to 5% of one or more ethylene oxide or propylene oxide additives of the allyl derivative represented by The present invention relates to a method for producing an agrochemical emulsion with good storage stability and emulsifying property, which prevents the above and improves emulsifying performance. Ethoxylates of allyl derivatives represented by the above general formula of the present invention include, for example, phenyl cellosolve, O-phenylphenol propoxylate (2 moles of PO), distyrylphenol ethoxylate (2 moles of EO), tristyrylphenol ethoxylate (2 moles of EO), Examples include, but are not limited to, EO3 mol). In addition, the agricultural chemicals according to the present invention include organophosphorus agents; for example, 3-diethoxyphosphorylthiomethyl-6-chlorobenzoxazolone (phosalone), dimethyldicarbethoxyethyldithiophosphate (malathion), dimethyl-P-cyanophenylene ruthiophosphate (Cyanox), dimethyl (3-methyl-4-nitrophenyl) thiophosphate (fenitrothion), O-O-dimethyl-O-[3-methyl-
4-(Methylthio)phenyl]thiophosphate (Fenthion), O-ethyl-S,S-diphenyldithiophosphate (Edifuenphos),
Carbamate agents; for example, 2-secondary-butylphenyl-N-methyl carbamate (Batusa),
1-naphthyl-N-methylcarbamate (NAC), S-(2-chlorobenzyl)N,N-
diethylthiocarbamate (orzobencarp),
3-methoxycarbonylaminophenyl-N-
Examples include, but are not limited to, (3'-methylphenyl) carbamate (fuemedifum), pyrethroids; examples include pyrethrin, phenothrin, permethrin, and fuenvalerate. The emulsifier used in formulation is the one used in ordinary pesticide emulsions, and the nonionic surfactant is polyoxyethylene (EO 10 to 30 moles).
Examples include styryl (or benzyl) phenyl (or phenyl phenyl) ether, polyoxyethylene (EO 10 to 50 moles) castor oil ether, polyoxyethylene fatty acid ester, polyoxyethylene sorbitan alkylate, and the like. Typical anionic surfactants include dodecylbenzenesulfonic acid calcium salt and salts of various amines. These surfactants are blended to provide optimal natural emulsifying properties and emulsion stability. The amount of the chemical substance added in the present invention is 0.5 to 5% in the emulsion.
is sufficient, and an appropriate usage rate is selected depending on the purpose. Further, it is also possible to use a stabilizer in combination, if necessary. Although the mechanism by which the chemical substance of the present invention prevents crystal precipitation and the formation of "caste" is not clear, it is possible that nonionic surfactants, anionic surfactants, and agricultural chemical substances interact with each other by intervening between their molecules. It is thought that it affects the affinity and solvency, and that some of it is oriented on the surface of the emulsion to prevent the formation of "cage" caused by the drug substance, the anionic surfactant, and moisture in the air. Japanese Patent Publication No. 46-6438 describes a manufacturing method for improving emulsion stability by adding alcohols such as butyl alcohol, amyl alcohol, and cyclohexanol to organic phosphorus emulsions; however, such lower alcohols are generally used. The addition of is not preferable especially for organophosphorus drug substances which are easily hydrolyzed. Furthermore, it is often observed that such emulsions undergo discoloration and precipitation during long-term storage. On the other hand, the substance of the present invention is an ethoxylate of an allyl derivative having an ether bond in its structure, and can be said to be a completely new invention. Next, examples according to the present invention will be given. Example: Effect of preventing crystal precipitation and coloring A cyanox emulsion with the following formulation was stored in a thermostat at 50° C., and the presence or absence of crystal precipitation, coloring, etc. was visually observed.
【表】【table】
【表】
実施例
結晶の析出防止効果
下記処方フエニトロチオン高濃度乳剤を50℃恒
温器中に保存し結晶析出の有無を肉眼観察した。[Table] Example: Effect of preventing crystal precipitation A high-concentration fenitrothion emulsion with the following formulation was stored in a thermostat at 50°C, and the presence or absence of crystal precipitation was visually observed.
【表】【table】
【表】【table】
【表】
実施例
乳化性能試験
下記処方乳剤の1000倍エマルジヨンにおける初
期乳化性と１時間後の安定性を観察した。[Table] Example Emulsifying performance test The initial emulsifying property and stability after 1 hour of the emulsion with the following formulation in a 1000 times emulsion were observed.
【表】【table】
【表】
〜 〜
c；沈殿
以上の結果、本発明により製造した農薬乳剤
は、保存性に優れ、かつ乳化性の良好であること
がわかる。【table】 ~ ~
c: Precipitation The above results show that the agricultural chemical emulsion produced according to the present invention has excellent storage stability and good emulsifying properties.
Claims (1)
リル基を、R2は水素原子又はメチル基を、ｎは
１〜３の整数を、ｍは１〜２の整数をそれぞれ示
す。］ によつて表わされるアリル誘導体のエチレンオキ
サイド又はプロピレンオキサイド付加物の一種又
は二種以上を乳剤中に0.5〜５％添加することを
特徴とする保存性及び乳化性の良好な農薬乳剤の
製法。[Claims] 1. When producing a pesticide emulsion, the following general formula [However, in the formula, R 1 represents a hydrogen atom, a phenyl group, or a styryl group, R 2 represents a hydrogen atom or a methyl group, n represents an integer of 1 to 3, and m represents an integer of 1 to 2. ] A method for producing an agrochemical emulsion with good storage stability and emulsifying property, characterized by adding 0.5 to 5% of one or more adducts of ethylene oxide or propylene oxide of an allyl derivative represented by the following to the emulsion.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59161024A JPS6137702A (en) | 1984-07-31 | 1984-07-31 | Preparation of agricultural chemical emulsion having improved preservation quality and emulsifiablity |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59161024A JPS6137702A (en) | 1984-07-31 | 1984-07-31 | Preparation of agricultural chemical emulsion having improved preservation quality and emulsifiablity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6137702A JPS6137702A (en) | 1986-02-22 |
| JPS6361281B2 true JPS6361281B2 (en) | 1988-11-28 |
Family
ID=15727134
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59161024A Granted JPS6137702A (en) | 1984-07-31 | 1984-07-31 | Preparation of agricultural chemical emulsion having improved preservation quality and emulsifiablity |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6137702A (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5829606A (en) * | 1981-08-03 | 1983-02-21 | デゾヴアーグ・マテリアルシユツツ・ゲゼルシヤフト・ミツト・ベシュレンクテル・ハフツング | Wood antiseptic condensate and conservative agent for wood or wood material manufactured from said condensate and manufacture of wood antiseptic condensate |
-
1984
- 1984-07-31 JP JP59161024A patent/JPS6137702A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5829606A (en) * | 1981-08-03 | 1983-02-21 | デゾヴアーグ・マテリアルシユツツ・ゲゼルシヤフト・ミツト・ベシュレンクテル・ハフツング | Wood antiseptic condensate and conservative agent for wood or wood material manufactured from said condensate and manufacture of wood antiseptic condensate |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6137702A (en) | 1986-02-22 |
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