JPS6333305A - Insecticidal and acaricidal composition - Google Patents
Insecticidal and acaricidal compositionInfo
- Publication number
- JPS6333305A JPS6333305A JP61176379A JP17637986A JPS6333305A JP S6333305 A JPS6333305 A JP S6333305A JP 61176379 A JP61176379 A JP 61176379A JP 17637986 A JP17637986 A JP 17637986A JP S6333305 A JPS6333305 A JP S6333305A
- Authority
- JP
- Japan
- Prior art keywords
- glycol
- group
- parts
- active ingredient
- average molecular
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 29
- 230000000895 acaricidal effect Effects 0.000 title claims abstract description 7
- 230000000749 insecticidal effect Effects 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- 239000004480 active ingredient Substances 0.000 claims abstract description 24
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000002202 Polyethylene glycol Substances 0.000 claims abstract description 17
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 17
- 229920001451 polypropylene glycol Polymers 0.000 claims abstract description 16
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000005995 Aluminium silicate Substances 0.000 claims abstract description 14
- 235000012211 aluminium silicate Nutrition 0.000 claims abstract description 14
- 239000004927 clay Substances 0.000 claims abstract description 14
- 239000007787 solid Substances 0.000 claims abstract description 13
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 12
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 235000011187 glycerol Nutrition 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims abstract description 3
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 3
- -1 polyglycerin Chemical compound 0.000 claims description 23
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 9
- CZMAXQOXGAWNDO-UHFFFAOYSA-N propane-1,1,2-triol Chemical compound CC(O)C(O)O CZMAXQOXGAWNDO-UHFFFAOYSA-N 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 229910052903 pyrophyllite Inorganic materials 0.000 claims description 2
- 239000003381 stabilizer Substances 0.000 abstract description 9
- 239000002917 insecticide Substances 0.000 abstract description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract description 2
- 239000005977 Ethylene Substances 0.000 abstract description 2
- 239000000642 acaricide Substances 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Chemical group C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract 1
- 238000012423 maintenance Methods 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- 238000002156 mixing Methods 0.000 abstract 1
- 239000000843 powder Substances 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 7
- 239000000454 talc Substances 0.000 description 6
- 229910052623 talc Inorganic materials 0.000 description 6
- 238000009472 formulation Methods 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
- 239000003905 agrochemical Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 2
- ZRPAUEVGEGEPFQ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2 ZRPAUEVGEGEPFQ-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000008262 pumice Substances 0.000 description 2
- 230000004083 survival effect Effects 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241001414720 Cicadellidae Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241001556089 Nilaparvata lugens Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 125000003302 alkenyloxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 229910052586 apatite Inorganic materials 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 239000011230 binding agent Substances 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
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
- 238000003869 coulometry Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical group O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 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
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- QPPQHRDVPBTVEV-UHFFFAOYSA-N isopropyl dihydrogen phosphate Chemical compound CC(C)OP(O)(O)=O QPPQHRDVPBTVEV-UHFFFAOYSA-N 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000010721 machine oil Substances 0.000 description 1
- 239000011419 magnesium lime Substances 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229910052625 palygorskite Chemical group 0.000 description 1
- VSIIXMUUUJUKCM-UHFFFAOYSA-D pentacalcium;fluoride;triphosphate Chemical compound [F-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O VSIIXMUUUJUKCM-UHFFFAOYSA-D 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 244000045561 useful plants Species 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
Abstract
Description
【発明の詳細な説明】
〈産業上の利用分野〉
本発明は、一段式（１）
〔式中、Ｘは基−ＣＨ＝または窒素原子を表わし、Ｙは
酸素原子またはメチレン基を表わｔＲｌは水素原子また
は弗素原子を表わし、Ｒ２はメチル基を表わし、島はメ
チル基もしくはエチニル基を表わすか、またはＲ２とＲ
８とでエチレン基を形成していてもよい。Ｒ４はメチル
基またはＲ換フェニル基を表わす。〕で示される化合物
を有効成分とする固型製剤の、安定かつ高い生物効力を
保持する組成物に関するものである。Detailed Description of the Invention <Industrial Application Field> The present invention provides a one-stage formula (1) [wherein, X represents a group -CH= or a nitrogen atom, and Y represents an oxygen atom or a methylene group; represents a hydrogen atom or a fluorine atom, R2 represents a methyl group, island represents a methyl group or an ethynyl group, or R2 and R
8 may form an ethylene group. R4 represents a methyl group or an R-substituted phenyl group. ] The present invention relates to a solid formulation containing a compound shown in the following as an active ingredient, which maintains stable and high biological efficacy.
〈従来の技術〉
通常、農薬は、有効成分を容易にかつ効率よく散布して
農薬の効力を最大限に発揮させるために穏々の剤型に製
剤されて使用されている。<Prior Art> Pesticides are usually formulated into mild dosage forms in order to easily and efficiently disperse the active ingredients and maximize the effectiveness of the pesticide.
すなわち、有効成分を適当な不活性担体に、要するなら
補助剤と一緒に、適当な割合に配合して、溶解、分散、
懸濁、混合、含浸、造粒、吸着もしくは付着させ適宜の
剤型、たとえば懸濁液、乳剤、水和剤、粒剤、粉剤等に
製剤される。That is, the active ingredient is blended with a suitable inert carrier, together with adjuvants if necessary, in an appropriate ratio, dissolved, dispersed,
The ingredients are suspended, mixed, impregnated, granulated, adsorbed or adhered to form an appropriate dosage form, such as a suspension, emulsion, wettable powder, granule, or powder.
水和剤、粒剤、粉剤等の固形製剤に使用することのでき
る固体の不活性担体としては、通常物エキス抽出後の残
量等の植物性粉末；カオリナイト群、モンモリロナイト
群あるいはアタパルジャイト群で代表されるクレー類、
タルク、雲母、葉ロウ石、軽石、バーミキュライト、石
こう、炭酸カルシウム、ドロマイト、けいそう土、マグ
ネシウム石灰、りん灰石、ゼオライト、無水ケイ酸、合
成ケイ酸カルシウム等の無機鉱物性粉末；硫安、燐安、
硝安、尿素、塩安等の化学肥料、堆肥等をあげることが
でき、これらの−Ｕもしくは二環以上を混合して使用さ
れる。Solid inert carriers that can be used in solid preparations such as wettable powders, granules, and powders include vegetable powders such as those remaining after extract extraction; kaolinite group, montmorillonite group, or attapulgite group; Represented clays,
Inorganic mineral powders such as talc, mica, phyllite, pumice, vermiculite, gypsum, calcium carbonate, dolomite, diatomaceous earth, magnesium lime, apatite, zeolite, silicic anhydride, synthetic calcium silicate; ammonium sulfate, phosphorus Cheap,
Chemical fertilizers such as ammonium nitrate, urea, and ammonium chloride, compost, etc. can be mentioned, and -U or two or more rings of these are used as a mixture.
〈発明が解決しようとする問題点〉
農薬に含有する有効成分の経時変化は、農薬の効力低下
、効果の好ましくない変動および分解生成物による予期
せぬ薬害等を生じさせ、農薬の品質を著しく低下させる
原因となる。そのため農薬の使用薬量もしくは使用回数
を増加させるとか、または有用植物体への二次的被害を
防止するための新たな処置を施さねばならず、余計な経
費と労力が必要となる。さらに農薬をその不安定性のゆ
えに長期間貯蔵することができない場合、工業規模での
量産にも不適である。<Problems to be solved by the invention> Changes in the active ingredients contained in agricultural chemicals over time can cause a decrease in the efficacy of the agricultural chemicals, undesirable fluctuations in effectiveness, unexpected chemical damage due to decomposition products, etc., and can significantly deteriorate the quality of the agricultural chemicals. This causes a decrease in the amount of water. Therefore, it is necessary to increase the amount or frequency of use of pesticides, or to take new measures to prevent secondary damage to useful plants, which requires extra expense and labor. Furthermore, if pesticides cannot be stored for long periods of time due to their instability, they are also unsuitable for mass production on an industrial scale.
このように有効成分についての経時変化の有無およびそ
の防止方法は農薬の種類の如何を問わず、常に検討され
なければならない重要な課題である、
一般式（１）で示される化合物は、特開和６１−７６４
６２号、特開昭６０−１８８８０４号、特開昭５９−１
０８７８８号各公報等に記載されており、殺虫、殺ダニ
剤として有用なものであるが、これらの化合物は、固体
担体により分解を受は易く、特に汎用されるカオリンク
レー、セリサイト、タルクおよびパイロフィライトを固
体担体とする場合は分解が著しく、シたがって経時変化
が非常に大きいという欠点を有していた。In this way, whether or not active ingredients change over time and how to prevent them are important issues that must always be considered, regardless of the type of pesticide. Japanese 61-764
No. 62, JP-A-60-188804, JP-A-59-1
No. 08788, etc., and are useful as insecticides and acaricides, but these compounds are easily decomposed by solid carriers, and are particularly useful for commonly used kaolin clay, sericite, talc, and When pyrophyllite is used as a solid carrier, it has the disadvantage that it decomposes significantly and therefore changes over time.
〈問題点を解決するための手段〉
木発明者らは、一般式中で示される化合物の安定な固型
製剤を得るため種々研究を重ねた結果、安定化剤として
、グリセリン、ポリグリセリン、エチレングリコール、
ポリエチレングリコール、プロピレングリコール、ポリ
プロピレングリコール、ポリオキシエチレンオキシプロ
ピレングリコールおよびポリオキシエチレンオキシプロ
ピレンオキシブチレングリコールから選ばれた１１以と
を用いることにより、所期の目的を達成することができ
ることを確認し、本発明を完成した。<Means for solving the problem> As a result of various studies to obtain a stable solid preparation of the compound represented by the general formula, the inventors discovered that glycerin, polyglycerin, and ethylene were used as stabilizers. glycol,
Confirm that the intended purpose can be achieved by using 11 or more selected from polyethylene glycol, propylene glycol, polypropylene glycol, polyoxyethylene oxypropylene glycol, and polyoxyethylene oxypropylene oxybutylene glycol, The invention has been completed.
すなわち、本発明は、一般式（１）で示される化合物を
有効成分とする固型製剤中に、上記の安定化剤から選ば
れた１種以上を含有する安定でかつ高い生物効力を保持
する殺虫、殺ダニ組成物である。That is, the present invention provides a solid preparation containing the compound represented by general formula (1) as an active ingredient, which contains one or more stabilizers selected from the above stabilizers and maintains stable and high biological efficacy. It is an insecticidal and acaricidal composition.
一般式ＣＩ）で示される化合物中、へが表わす置換フェ
ニル基の誼換基としては、たとえばハロゲン原子、低級
アルキル基、トリフルオロメチルｉ、低級アルコキシル
基、低級アルケニルオキシ基、ハロゲン置換低級アルコ
キシル基等をあげることができ、化合物の見体例として
は、たとえば下記（第１表）の化合物をあげることがで
きるが、本発明はもちろんこれらに限定されるものでは
なく、またこれらの化合物の光学活性体も含まれるもの
である。In the compound represented by the general formula CI), examples of substituents for the substituted phenyl group represented by H include a halogen atom, a lower alkyl group, trifluoromethyl i, a lower alkoxyl group, a lower alkenyloxy group, and a halogen-substituted lower alkoxyl group. Examples of compounds include the compounds shown below (Table 1), but the present invention is of course not limited to these, and the optical activity of these compounds It also includes the body.
第 １ 表
これらの化合物は、２種以上を混合して用いてもよく、
また他の薬剤、たとえば有機リン剤、カーバメート剤、
ピレスロイド剤等を混合して用いてもよい。Table 1 These compounds may be used in combination of two or more,
Also, other drugs such as organophosphorus agents, carbamate agents,
A mixture of pyrethroids and the like may be used.
本発明において、ポリエチレングリコールとしては、ジ
エチレングリコール（分子ｔ １０６）をはじめそれ以
上の平均分子量のものが用いられ、平均分子量が６００
までの４ｅリエチレングリコールが室温で液状を呈する
ので本組成物の製造上有利である。ポリプロピレングリ
コールは、ジプロピレングリコール（分子１１３４）を
はじめ、それ以上の平均分子−のものが用いられ、平均
分子量が４０００までのポリプロピレングリコールが粘
度が低いことから本組成物の製造上有利である。また、
ポリオキシエチレンオキシプロピレングリコール、ポリ
オキシエチレンオキシブチレングリコールおよびポリオ
キシプロピレンオキシブチレングリコールは、各々平均
分子ｆｉ１０００以上のものが一般的に用いられ、同様
の理由で室温で液状を呈するものが好ましい。これらの
うち、ポリエチレングリコールおよびポリプロピレング
リコールは本組成吻の裂ａ面および経済・住の点からイ
利であるつ
本発明の１狙成物は、有効成分としての一般式（１）で
示される化合物を厘量比で０．１〜４０部、安定化剤と
しての前述のグリセリン、ポリグリセリン、エチレング
リコール、ポリエチレングリコール、プロピレングリコ
ール、ポリプロピレングリコール◇を０．１〜８０部、
好ましくは０．５〜１０部、残部の一体担体を含有する
が、必要に応じて暮々の界面活性剤、結合剤、安定剤、
マシン油、流動パラフィン、動植物油等の製剤補助剤を
併用することもできる。In the present invention, as the polyethylene glycol, polyethylene glycol having an average molecular weight of 600 or more is used, including diethylene glycol (molecule t 106).
The above 4e-lyethylene glycols are liquid at room temperature, which is advantageous in the production of the present composition. The polypropylene glycol used is dipropylene glycol (molecular weight 1134) or higher average molecular weight, and polypropylene glycol having an average molecular weight of up to 4000 is advantageous in the production of the present composition because of its low viscosity. Also,
Polyoxyethylene oxypropylene glycol, polyoxyethylene oxybutylene glycol, and polyoxypropylene oxybutylene glycol each having an average molecular fi of 1000 or more are generally used, and for the same reason, those that are liquid at room temperature are preferred. Among these, polyethylene glycol and polypropylene glycol are advantageous from the aspect of the present composition and from the viewpoint of economy and housing.One target product of the present invention is represented by the general formula (1) as an active ingredient. 0.1 to 40 parts of the compound, 0.1 to 80 parts of the above-mentioned glycerin, polyglycerin, ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol ◇ as a stabilizer,
It preferably contains 0.5 to 10 parts and the remainder is an integral carrier, but if necessary, it may contain a surfactant, a binder, a stabilizer,
Formulation aids such as machine oil, liquid paraffin, animal and vegetable oils can also be used in combination.
〈実施例〉
以下、実施例、比較例および試験例をあげ、本発明をさ
らに詳細に説明するが、本発明はこれらに限定されるも
のではない。<Examples> Hereinafter, the present invention will be explained in more detail by referring to Examples, Comparative Examples, and Test Examples, but the present invention is not limited thereto.
なお、有効成分としての一般式（１）で示される化合物
は、前記の化合物番号で示し、また部は電量部を表わす
。The compound represented by the general formula (1) as an active ingredient is shown by the above-mentioned compound number, and parts represent coulometric parts.
実施例１
化合物（ｔ） ０．５部、ＰＡＰ（安定剤エイソプロピ
ルアシドホスフェート）Ｏ−ａＳ、ホワイトカーボン２
部、カオリンクレー９６．２部に各々ポリエチレングリ
コール（平均分子量２００）またはポリプロピレングリ
コール（平均分子ｆｆ１２０００）１部を加え、混合機
中で均一に混合し、有効成分が０，５％の各々の粉剤を
得ろう
実施例２
化合物（２） ０．５部、ＰＡＰ（前記）０．８部、ホ
ワイトカーボン１部、カオリンクレーまたはタルク９７
．２部に各々ポリエチレングリコール（平均分子ｔ２０
０ ）またはポリプロピレングリコール（平均分子量２
０００）１部を加え、混合機中で均一に混合し、有効成
分が０．５％の各々の粉剤を得る。Example 1 Compound (t) 0.5 part, PAP (stabilizer isopropyl acid phosphate) O-aS, white carbon 2
1 part of polyethylene glycol (average molecular weight 200) or polypropylene glycol (average molecular weight FF 12000) was added to 96.2 parts of kaolin clay and mixed uniformly in a mixer to form each powder containing 0.5% of the active ingredient. Example 2 Compound (2) 0.5 parts, PAP (above) 0.8 parts, white carbon 1 part, kaolin clay or talc 97
．． Two parts each contain polyethylene glycol (average molecular t20
0 ) or polypropylene glycol (average molecular weight 2
000) and mixed uniformly in a mixer to obtain respective powders containing 0.5% of active ingredient.
実施例８ 化合物（４）１部、ＰＡＰ（前記）０．８部、ホ 。Example 8 1 part of compound (4), 0.8 part of PAP (above), e.
ワイドカーボン４部、カオリンクレー９２．７部に各々
ポリエチレングリコール（平均分子ｆｄ２００）または
ポリプロピレングリコール（平均分子量２０００）２部
を加え、混合機中で均一に混合し、有効成分が１％の各
々の粉剤を得る。Add 2 parts of polyethylene glycol (average molecular weight FD200) or polypropylene glycol (average molecular weight 2000) to 4 parts of wide carbon and 92.7 parts of kaolin clay, mix uniformly in a mixer, and mix each with an active ingredient content of 1%. Get the powder.
実右例４
化合物（５） ０．５部、ＦＡＩ’（前記）０．３部、
ホワイトカーボン２部、カオリンクレーもしくはタルク
９６．２部に各々ポリエチレングリコール（平均分子量
２０Ｇ）または〜１！リプロピレングリコール（平均分
子１１２０００）１部を加え、混合機中で均一に混合し
、有効成分が０．５％の各々の粉剤を得る。Actual Example 4 Compound (5) 0.5 part, FAI' (above) 0.3 part,
2 parts of white carbon, 96.2 parts of kaolin clay or talc, and polyethylene glycol (average molecular weight 20G) or ~1! Add 1 part of lipropylene glycol (average molecular weight 112,000) and mix uniformly in a mixer to obtain respective powders containing 0.5% of active ingredient.
実３例５
化合物（６） ０．５部、ＰＡＰ（前記）０．３部、ホ
ワイトカーボン１部、カオリンクレー９６．２部に各々
ポリエチレングリコール（平均分子９２００）またはポ
リプロピレングリコール（平均分子！ｊｔ２０００）１
部を加え、混合機中で均一に混合し、有効成分が０．５
％の各々の粉剤を得る。Practical Example 5 0.5 parts of compound (6), 0.3 parts of PAP (above), 1 part of white carbon, 96.2 parts of kaolin clay, and polyethylene glycol (average molecular weight: 9200) or polypropylene glycol (average molecular weight: jt2000), respectively. )1
% and mix uniformly in a mixer until the active ingredient is 0.5
% of each powder.
実施例６
化合物（１） 、 （２） 、 （！ｌ） 、 （４）
、 （５）または（６）各々１０３、ッ７．ボーア、
■２４９５Ｇ（東うえや（４、製の乳化剤）２部、サン
エキス■Ｐ−２０１（出画国策パルプ（株）裂の分散剤
）２部、ホワイトカーボン１５部、カオリンクレーまた
はけいそう土６６部に各々ポリエチレングリコール（平
均分子１２００）またはポリプロピレングリコール（平
均分子ｆｉ２０００）５部を加え、混合機中で均一に混
合し、有効成分が１０％の各々の水和剤を得る。Example 6 Compounds (1), (2), (!l), (4)
, (5) or (6) each 103, 7. Bohr,
■ 2 parts of 2495G (emulsifier manufactured by Higashiueya (4)), Sun Extract ■ 2 parts of P-201 (dispersant manufactured by Izuga Kokusaku Pulp Co., Ltd.), 15 parts of white carbon, kaolin clay or diatomaceous earth 66 5 parts of polyethylene glycol (average molecular weight 1200) or polypropylene glycol (average molecular weight fi 2000) are added to each part and mixed uniformly in a mixer to obtain each wettable powder containing 10% of the active ingredient.
実施例７
化合物（１） 、 （２） 、 （３） 、 （４）
、 （５）または（６）各々１部、軽石９４部に各々ポ
リエチレングリコール（平均分子１１２００）またはポ
リプロピレングリコール（平均分子［２０００）５部を
加え、均一に混合吸油し、有効成分が１％の各々の粒剤
を得ろう
比較例１
化合物（１） ０．５部、ＰＡＰ（前記）０．８部、ホ
ワイトカーボン１部、カオリンクレー９８．２部を混合
機中で均一に混合し、有効成分が０．５％の粉剤を得る
。Example 7 Compounds (1), (2), (3), (4)
, Add 1 part each of (5) or (6) and 5 parts of polyethylene glycol (average molecular weight: 11,200) or polypropylene glycol (average molecular weight: [2,000) to 94 parts of pumice, mix evenly, and absorb the oil to obtain a mixture containing 1% of the active ingredient. Comparative Example 1 To obtain each granule, 0.5 parts of compound (1), 0.8 parts of PAP (above), 1 part of white carbon, and 98.2 parts of kaolin clay were mixed uniformly in a mixer, and an effective A powder containing 0.5% of the ingredients is obtained.
比較例２
化合物（２） ０．５部、ＰＡＰ（前記）０．３部、ホ
ワイトカーボン１部に各々カオリンクレーまたはタルク
９８．２部を加え、混合機中で均一に混訃し、有効成分
が０．５％の各々の粉剤を得る。Comparative Example 2 98.2 parts of kaolin clay or talc were added to 0.5 parts of compound (2), 0.3 parts of PAP (above), and 1 part of white carbon, and the mixture was uniformly mixed in a mixer to remove the active ingredients. 0.5% of each powder is obtained.
比較例８
化合物（４）１部、ＰＡＰ （前記）０．８部、ホワイ
トカーボン２部、カオリンクレー９６．７部を混合機中
で均一に混合し、有効成分が１％の粉剤を得る。Comparative Example 8 1 part of compound (4), 0.8 parts of PAP (above), 2 parts of white carbon, and 96.7 parts of kaolin clay are uniformly mixed in a mixer to obtain a powder containing 1% of the active ingredient.
比較例４
化合物（５） ０．５部、ＰＡＰ （前記）０．８部、
ホワイトカーボン１部に各々カオリンクレーまたはタル
ク９８．２部を加え、混合機中で均一に混合し、汀効成
分が０．５％の各々の粉剤を得る。Comparative Example 4 Compound (5) 0.5 part, PAP (above) 0.8 part,
98.2 parts of kaolin clay or talc are added to 1 part of white carbon, and mixed uniformly in a mixer to obtain powders containing 0.5% of the detergent component.
比俊例５
化合物（６） ０．５部をアセトン１０部に溶解し、カ
オリンクレー９９．５部を加九たのちアセトンを蒸発さ
せ、有効成分が０．５％の粉剤を得る。Example 5: Dissolve 0.5 parts of compound (6) in 10 parts of acetone, add 99.5 parts of kaolin clay, and evaporate the acetone to obtain a powder containing 0.5% of the active ingredient.
試験例１
実施例１．２．３．４．５および比較例１．２．８．４
．５で得られ組成物について、加熱保存試験を行ない、
有効成分の分解率を測定した。Test Example 1 Example 1.2.3.4.5 and Comparative Example 1.2.8.4
．． A heating storage test was conducted on the composition obtained in step 5,
The decomposition rate of the active ingredient was measured.
結果を第２．３．４．５および６表に示す。The results are shown in Tables 2.3.4.5 and 6.
ｆｇ２表
＼、
、 ＼
第３表
第 ４ 表
第５表
第６表
上記の結果より、本発明の組成物は従来の処方よりも安
定性に優れていることが明らかである。fg2 Table \, , \ Table 3 Table 4 Table 5 Table 6 From the above results, it is clear that the composition of the present invention has better stability than conventional formulations.
試験例２
直径７ｃＭ１、深さ７５１Ｉのプラスチックカップ植え
のイネ苗（２〜８葉期、約１０本／カップ）に、実施例
１（安定化剤がポリエチレングリコール（平均分子量が
２００）のもの）および実施例８（安定化剤がポリプロ
ピレングリコール（平均分子量が２０００）のもの）な
らびに比較例１および８で得られた粉剤５０ｑ（ｉｌｌ
ｓ／１０ａ相当）を散布した。これを金網かごで覆い、
Ｒ系ツマグロヨコバイ成虫またはトビイロウンカ成虫約
１５頭を放飼し、２４時間後に生死を調査した。さらに
所定日数後に上記供試虫を放飼し、２４時間後に生死を
調査した。Test Example 2 Rice seedlings (2-8 leaf stage, about 10 plants/cup) planted in plastic cups with a diameter of 7 cM1 and a depth of 751 I were treated with Example 1 (stabilizer was polyethylene glycol (average molecular weight 200)). and Example 8 (where the stabilizer is polypropylene glycol (average molecular weight: 2000)) and powders 50q (ill) obtained in Comparative Examples 1 and 8.
s/10a equivalent) was sprayed. Cover this with a wire mesh basket,
Approximately 15 R-series leafhopper adults or brown planthopper adults were released, and their survival and death were examined 24 hours later. Furthermore, after a predetermined number of days, the test insects were released, and 24 hours later, their survival and death were examined.
結果を第７および８表に示す。The results are shown in Tables 7 and 8.
【６１７表
箇８表
上記の結果より、本発明の組成物は、従来の処方に比べ
Ｕい殺虫効力を示すことが明らかである。From the above results, it is clear that the composition of the present invention exhibits greater insecticidal efficacy than conventional formulations.
〈発明の効果〉
本発明の殺虫、殺ダニ組成物は、従来の処方のものに比
し、有効成分の安定性に優れ、また高い生物効力を保持
し得る。<Effects of the Invention> The insecticidal and acaricidal compositions of the present invention have excellent stability of active ingredients and can maintain high biological efficacy compared to conventional formulations.
手続補正書（自発）
昭和６２年６月１２日
１、事件の表示
昭和６１年 特許願第 １７６８７９ 号２、発明の
名称
殺虫、殺ダニ組成物
３、補正をする者
事件との関係 特許出願人
住 所 大阪市東区北浜５丁目１５番地名称 （２０
９）住友化学工業株式会社代表者 森 英
雄
４、代理人
住 所 大阪市東区北浜５丁目１５番地６、補正の内
容
明細書第６頁第１２行目〜第１３行目に、「ポリオキシ
エチレンオキシプロピレングリコールおよび」とあるの
を［ポリオキシェチレンオ寝ノ
キシプロピレグリコール、ポリオキシエチレンオキシブ
チレングリコールおよび寸と訂正する。Procedural amendment (voluntary) June 12, 1985 1. Indication of the case 1988 Patent Application No. 176879 2. Name of the invention Insecticide, acaricidal composition 3. Person making the amendment Relationship to the case Patent applicant Address 5-15 Kitahama, Higashi-ku, Osaka Name (20
9) Sumitomo Chemical Co., Ltd. Representative: Hideo Mori 4, Agent address: 5-15-6 Kitahama, Higashi-ku, Osaka City, page 6, lines 12 to 13 of the statement of contents of the amendment, “Polyoxy ``Ethylene oxypropylene glycol and'' has been corrected to ``polyoxyethylene oxypropylene glycol, polyoxyethylene oxybutylene glycol, and polyoxyethylene oxybutylene glycol.''
以上that's all
Claims (4)
酸素原子またはメチレン基を表 わす。Ｒ＿１は水素原子または弗素原子を表わし、Ｒ＿
２はメチル基を表わし、Ｒ＿３はメチル基もしくはエチ
ニル基を表わすか、またはＲ＿２とＲ＿３とでエチレン
基を形成していてもよい。Ｒ＿４はメチル基または置換
フェニル基を表わす。〕 で示される化合物を有効成分とする固型製剤中に、グリ
セリン、ポリグリセリン、エチレングリコール、ポリエ
チレングリコール、プロピレングリコール、ポリプロピ
レングリコール、ポリオキシエチレンオキシプロピレン
グリコール、ポリオキシエチレンオキシブチレングリコ
ールおよびポリオキシエチレンオキシプロピレンオキシ
ブチレングリコールから選ばれた１種以上の化合物を含
有することを特徴とする殺虫、殺ダニ組成物、(1) General formula▲ Numerical formula, chemical formula, table, etc.▼ [In the formula, X represents a group -CH= or a nitrogen atom, and Y represents an oxygen atom or a methylene group. R_1 represents a hydrogen atom or a fluorine atom, R_1
2 represents a methyl group, R_3 represents a methyl group or an ethynyl group, or R_2 and R_3 may form an ethylene group. R_4 represents a methyl group or a substituted phenyl group. ] Glycerin, polyglycerin, ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, polyoxyethylene oxypropylene glycol, polyoxyethylene oxybutylene glycol, and polyoxyethylene are contained in solid preparations containing the compounds shown as active ingredients. Insecticidal and acaricidal compositions containing one or more compounds selected from oxypropylene oxybutylene glycol,
から６００の範囲である特許請求の範囲第１項記載の組
成物。(2) The average molecular weight of polyethylene glycol is 106
600.
４から４０００の範囲である特許請求の範囲第１項記載
の組成物。(3) The average molecular weight of polypropylene glycol is 13
4. The composition of claim 1 in the range of 4 to 4000.
イトまたはパイロフィライトである特許請求の範囲第１
項、第２項または第３項記載の組成物。(4) Claim 1, wherein the solid carrier of the solid preparation is kaolin clay, sericite or pyrophyllite.
The composition according to item 1, 2 or 3.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61176379A JPS6333305A (en) | 1986-07-25 | 1986-07-25 | Insecticidal and acaricidal composition |
| KR1019870008006A KR880001209A (en) | 1986-07-25 | 1987-07-23 | Pesticides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61176379A JPS6333305A (en) | 1986-07-25 | 1986-07-25 | Insecticidal and acaricidal composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6333305A true JPS6333305A (en) | 1988-02-13 |
Family
ID=16012607
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61176379A Pending JPS6333305A (en) | 1986-07-25 | 1986-07-25 | Insecticidal and acaricidal composition |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS6333305A (en) |
| KR (1) | KR880001209A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2645709A1 (en) * | 1989-04-18 | 1990-10-19 | Sumitomo Chemical Co | EMULSIFIABLE SOLID PESTICIDE COMPOSITIONS |
| US5912208A (en) * | 1991-10-31 | 1999-06-15 | Kao Corporation | Agricultural chemical composition |
| WO2001008481A1 (en) * | 1999-07-30 | 2001-02-08 | Clariant Gmbh | Pesticide preparations containing polyglycerin or polyglycerin derivatives |
| JP2008094749A (en) * | 2006-10-11 | 2008-04-24 | Nissan Chem Ind Ltd | Plant disease injury-control agent composition |
-
1986
- 1986-07-25 JP JP61176379A patent/JPS6333305A/en active Pending
-
1987
- 1987-07-23 KR KR1019870008006A patent/KR880001209A/en not_active Application Discontinuation
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2645709A1 (en) * | 1989-04-18 | 1990-10-19 | Sumitomo Chemical Co | EMULSIFIABLE SOLID PESTICIDE COMPOSITIONS |
| US5912208A (en) * | 1991-10-31 | 1999-06-15 | Kao Corporation | Agricultural chemical composition |
| WO2001008481A1 (en) * | 1999-07-30 | 2001-02-08 | Clariant Gmbh | Pesticide preparations containing polyglycerin or polyglycerin derivatives |
| JP2008094749A (en) * | 2006-10-11 | 2008-04-24 | Nissan Chem Ind Ltd | Plant disease injury-control agent composition |
Also Published As
| Publication number | Publication date |
|---|---|
| KR880001209A (en) | 1988-04-22 |
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