JPH0617284B2 - Microbicide - Google Patents
MicrobicideInfo
- Publication number
- JPH0617284B2 JPH0617284B2 JP61186222A JP18622286A JPH0617284B2 JP H0617284 B2 JPH0617284 B2 JP H0617284B2 JP 61186222 A JP61186222 A JP 61186222A JP 18622286 A JP18622286 A JP 18622286A JP H0617284 B2 JPH0617284 B2 JP H0617284B2
- Authority
- JP
- Japan
- Prior art keywords
- parts
- compound
- ethylhexyl
- bis
- succinate
- 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 - Lifetime
Links
Description
【発明の詳細な説明】 本発明は、３−ヨード−２−プロピニル ブチル カー
バメート、３−ブロモ−2,3−ジヨード−２−プロペニ
ル エチル カーボナート、2,3,3−トリヨードアリル
アルコール及びパラ−クロロフェニル−３−ヨードプロ
プロパルギル ホルマールからなる群(A)から選ばれた
１以上の化合物に１，４−ビス−（２−エチルヘキシ
ル）−スルホ−コハク酸ナトリウム(B)を配合したこと
を特徴とする殺微生物剤に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention provides 3-iodo-2-propynyl butyl carbamate, 3-bromo-2,3-diiodo-2-propenyl ethyl carbonate, 2,3,3-triiodoallyl alcohol and para- It is characterized in that sodium 1,4-bis- (2-ethylhexyl) -sulfo-succinate (B) is blended with one or more compounds selected from the group (A) consisting of chlorophenyl-3-iodopropargyl formal. The present invention relates to a microbicide.
微生物による汚染又は被害は医薬品、食品、農業分野の
みならず、木材、繊維、皮革、塗料、建材、ゴム、プラ
スチック等の分野も含まれ、多岐にわたつている。Contamination or damage by microorganisms is not limited to the fields of medicine, food and agriculture, but includes fields of wood, textiles, leather, paints, building materials, rubber, plastics, etc.
木材、繊維、皮革、塗料、建材、ゴム等の分野で、特に
被害をおよぼす微生物類は、オオウズラタケ、ワタグサ
レタケ、カワラタケ、ヒイロタケ、ナミダタケ等の腐朽
菌やオフイオストマ（Ophiostoma）属、エンドコニデイ
オホラ（Endoconidiophora）属の変色菌及びペニシリウ
ム（Penicillium）属、アスペルギルス（Aspergillus）
属、リゾプス（Rhizopus）属、トリコデルマ（Trichode
rma）属等のカビ類で一般に他分野で問題とされる細菌
やその他の微生物類に比べ、薬剤感受性が低い。したが
って、これ等の微生物からの被害をふせぐ為には、強力
な殺微生物剤を、比較的高濃度で使用しなければならな
い。又、長期間にわたつて、高い効果が持続するものが
要求されるので、有効成分は、揮散や溶脱がなく、且
つ、水、熱、紫外線などにより分解されない耐候性を有
していることが必要である。In the fields of wood, textiles, leather, paints, building materials, rubber, etc., the microorganisms that are particularly damaging are rot fungi such as Pleurotus ostreatus, Pleurotus cornucopiae, Pleurotus cornucopiae, Pleurotus cornucopiae, Pleurotus cornucopiae, Ophiostoma (Ophiostoma) genus, Endoconidiophora ) Discoloring fungi and genus Penicillium, Aspergillus
Genus, Rhizopus, Trichoderma
The drug sensitivity is lower than that of bacteria and other microorganisms which are generally problematic in other fields in molds such as the genus rma). Therefore, in order to prevent damage from these microorganisms, powerful microbicides must be used in relatively high concentrations. Further, since it is required to have a high effect over a long period of time, the active ingredient should have weather resistance such that it does not volatilize or leach out, and is not decomposed by water, heat, ultraviolet rays or the like. is necessary.
又、これ等の性能の外、安全衛生上又は、環境汚染防止
上の配慮も重要である。In addition to these performances, it is also important to consider safety and hygiene or prevent environmental pollution.
本発明者等は、殺微生物剤について、長年に亘つて鋭意
検討を行い、微生物の細胞膜構造の一部になつている呼
吸酵素蛋白への障害作用を有する３−ヨード−２−プロ
ピニル ブチル カーバメート、３−ブロモ−2,3−ジ
ヨード−２−プロペニル エチル カーボナート、2,3,
3−トリヨードアリルアルコール及びパラ−クロロフェ
ニル−３−ヨードプロパルギル ホルマールからなる群
(A)から選ばれた１以上の化合物に、安価で、それ自体
殺微生物力を殆んど有しない1,4−ビス−（２−エチル
ヘキシル）−スルホ−コハク酸ナトリウム(B)を配合し
たことにより、協力作用により効力が増強され、殺微生
物剤の処理する成分量を減らすことができ、経済性、安
全衛生上等からも有利であること及び耐候性も改善され
るため、長期間にわたる残効性も期待できることを見出
して、本発明を完成した。The present inventors have conducted extensive studies on microbicides for many years, and have 3-iodo-2-propynyl butyl carbamate, which has a damaging effect on respiratory enzyme proteins that are part of the cell membrane structure of microorganisms, 3-bromo-2,3-diiodo-2-propenyl ethyl carbonate, 2,3,
Group consisting of 3-triiodoallyl alcohol and para-chlorophenyl-3-iodopropargyl formal
To one or more compounds selected from (A), 1,4-bis- (2-ethylhexyl) -sulfo-sodium succinate (B), which is inexpensive and has almost no microbicidal activity per se, is blended. As a result, the synergistic effect enhances the efficacy, the amount of the components to be treated by the microbicide can be reduced, and it is advantageous from the economical point of view, safety and hygiene, and the weather resistance is improved. The present invention has been completed by finding that residual effect can also be expected.
本発明の有効成分の１つであるＡ群の化合物、即ち、３
−ヨード−２−プロピニル ブチル カーバメート(A-
1)、３−ブロモ−2,3−ジヨード−２−プロペニル エ
チル カーボナート(A-2)、2,3,3−トリヨードアリルア
ルコール(A-3)及びパラ−クロロフェニル−３−ヨード
プロパルギル ホルマール(A-4)は、それぞれ、次式で
示され、 変色菌、腐朽菌、カビ等の防除剤として公知である。A group A compound which is one of the active ingredients of the present invention, that is, 3
-Iodo-2-propynyl butyl carbamate (A-
1), 3-bromo-2,3-diiodo-2-propenyl ethyl carbonate (A-2), 2,3,3-triiodoallyl alcohol (A-3) and para-chlorophenyl-3-iodopropargyl formal ( A-4) are respectively represented by the following equations, It is publicly known as a control agent for discoloring bacteria, rotting bacteria, mold and the like.
本発明のもう一方の有効成分である1,4−ビス−（２−
エチルヘキシル）−スルホ−コハク酸ナトリウム(B)
は、次式で示され、 医薬、化粧品、繊維、写真等の分野で、浸潤剤、分散剤
として公知であるが、殺微生物力を殆んど有しない。The other active ingredient of the present invention, 1,4-bis- (2-
Ethylhexyl) -sodium sulfo-succinate (B)
Is given by It is known as a wetting agent and a dispersant in the fields of medicine, cosmetics, fibers, photography, etc., but it has almost no microbicidal activity.
また毒性も低く、且つ、前記のＡ群の化合物に比し、安
価で製造される為、本発明の殺微生物剤は、安全衛生上
又は環境汚染防止上から見ても有用であり、又、経済的
でもある。Further, the toxicity is low, and since it is manufactured at a lower cost than the above-mentioned compounds of Group A, the microbicide of the present invention is useful from the viewpoint of safety and hygiene or prevention of environmental pollution. It is also economical.
本発明の殺微生物剤が適用される微生物としては、木材
等に寄生して腐朽等させる微生物なら特に制限されない
が、好適には、オオウズラタケ、ワタグサレタケ、カワ
ラタケ、ヒイロタケ、ナミダタケ等の腐朽菌、オフイオ
ストマ（Ophiostoma）属、エンドコニデイオホラ（Endo
conidiophora）属の変色菌及びペニシリウム（Penicill
ium）属、アスペルギルス（Aspergillus）属、リゾプス
（Rhizopus）属、トリコデルマ（Trichoderma）属等の
カビ類である。The microorganism to which the microbicide of the present invention is applied is not particularly limited as long as it is a microorganism that rots by parasitizing wood and the like, but it is preferable that Pseudomonas edulis, Pleurotus cornucopiae, Pleurotus cornucopiae, Pleurotus ostreatus, Namitake mushroom, etc. Genus Ophiostoma, Endo
conidiophora genus discoloring fungus and Penicillium (Penicill)
genus, Aspergillus genus, Rhizopus genus, Trichoderma genus and the like.
本発明の有効成分は、担体および必要に応じて他の補助
剤と混合して、工業用防カビ・防腐として通常用いられ
る製剤形態、例えば油溶性剤、乳剤、ペースト剤、粉
剤、水和剤、エアゾール剤、塗料等に調製されて使用さ
れる。The active ingredient of the present invention is mixed with a carrier and, if necessary, other auxiliaries, and is in a formulation form usually used for industrial fungicides and preservatives, such as oil-soluble agents, emulsions, pastes, powders, wettable powders. It is prepared and used for aerosols, paints, etc.
適当な担体としてはクレー、タルク、ベントナイト、カ
オリン、無水硅酸、炭酸カルシウム、木粉等の不活性固
体担体；ケロシン、リグロイン、キシレン、メチルナフ
タリン、ジメチルホルムアミド、ジメチルスルホキシド
等の液体担体；窒素ガス、ジメチルエーテル、フロンガ
ス、塩化ビニル単量体等の気体担体があげられる。製剤
の性状を改善し、防腐防カビ効果を高めるために適宜使
用される補助剤としては、例えば陰イオン性、陽イオン
性、非イオン性の界面活性剤やメチルセルロース、酢酸
ビニル樹脂、アルギン酸ソーダ等の種々の高分子化合物
等があげられる。もちろん、２−（４−チアゾリル）ベ
ンツイミダゾール（サイアベンダゾール）、N,N−ジメ
チル−Ｎ′−（ジクロロフルオロメチルチオ）−Ｎ′−
フェニルスルフアミド（ジクロフルアニド）あるいはベ
ンツアニリド系等の他の防腐・防カビ剤と併用でき、そ
れにより一層の効果向上をはかることも可能である。Suitable carriers include clay, talc, bentonite, kaolin, silicic acid anhydride, calcium carbonate, wood powder, and other inert solid carriers; kerosene, ligroin, xylene, methylnaphthalene, dimethylformamide, dimethyl sulfoxide, and other liquid carriers; nitrogen gas. Examples of the gas carrier include dimethyl ether, chlorofluorocarbon, vinyl chloride monomer and the like. Examples of the auxiliaries that are appropriately used to improve the properties of the preparation and enhance the antiseptic / antifungal effect include, for example, anionic, cationic and nonionic surfactants, methyl cellulose, vinyl acetate resin, sodium alginate, etc. Various polymer compounds and the like. Of course, 2- (4-thiazolyl) benzimidazole (thiabendazole), N, N-dimethyl-N '-(dichlorofluoromethylthio) -N'-
It can be used in combination with other antiseptic / antifungal agents such as phenylsulfamide (diclofluanid) or benzanilide series, and it is possible to further improve the effect.
実際の使用に際しての本発明の有効成分の含量は、製剤
の形態に従い広い範囲にわたつて変化させ得るが、一般
には(A)群の化合物は、使用される木材に対して0.２〜
１５重量％、好ましくは0.５〜５重量％の範囲が適当で
あり、1,4−ビス−（２−エチルヘキシル）−スルホ−
コハク酸ナトリウム(B)は、(A)群の化合物に対して重量
比で、１：0.０３〜１0.０、好ましくは、１：0.５〜５
である。The content of the active ingredient of the present invention in actual use can be varied over a wide range depending on the form of the preparation, but in general, the compound of the (A) group is 0.2 to the wood used.
A suitable range is 15% by weight, preferably 0.5-5% by weight, 1,4-bis- (2-ethylhexyl) -sulfo-
The sodium succinate (B) is used in a weight ratio of 1: 0.03 to 10.0, preferably 1: 0.5 to 5 with respect to the compounds of the (A) group.
Is.
次に本発明の殺微生物剤の効果を試験例によつて説明す
る。Next, the effect of the microbicide of the present invention will be described with reference to test examples.
〔試験例１〕 ３−ブロモ−2,3−ジヨード−２−プロペニルエチルカ
ボナート(A-2)と1,4−ビス−（２−エチルヘキシル）−
スルホ−コハク酸ナトリウム(B)を使用し、表１に示し
た処方の薬液を試製し、厚さ５mm、幅２０mm、長さ４０
mmの木材片に、各々１１０±１０ｇ／ｍ2宛塗布した試
験片を、（社）日本木材保存協会規格第１号の防腐効力
試験方法により試験し、効力値を求め、その結果を表２
に示した。[Test Example 1] 3-Bromo-2,3-diiodo-2-propenylethyl carbonate (A-2) and 1,4-bis- (2-ethylhexyl)-
Using sodium sulfo-succinate (B), a drug solution having the formulation shown in Table 1 was trial-produced, and the thickness was 5 mm, the width was 20 mm, and the length was 40 mm.
Test pieces applied to 110 mm ± 10 g / m 2 of each piece of wood were tested by the antiseptic efficacy test method of Japan Wood Preservation Association Standard No. 1, and the efficacy value was determined, and the results are shown in Table 2.
It was shown to.
〔試験例２〕 パラ−クロロフェニル−３−ヨードプロパルギルホルマ
ール(A-4)と1,4−ビス−（２−エチルヘキシル）−スル
ホ−コハク酸ナトリウム(B)を使用し、表３に示した処
方の薬液を試製し、試験例１と同様に試験を行い、表４
に示す結果を得た。 [Test Example 2] Para-chlorophenyl-3-iodopropargyl formal (A-4) and 1,4-bis- (2-ethylhexyl) -sodium sulfo-succinate (B) were used, and the formulations shown in Table 3 were used. The chemical solution of No. 4 was trial-produced, and the same test as in Test Example 1 was conducted.
The results shown in are obtained.
〔試験例３〕 ３−ヨード−２−プロピニル ブチル カルバメート(A
-1)と1,4−ビス−（２−エチルヘキシル）−スルホ−コ
ハク酸ナトリウム(B)を使用し、表５に示した処方の薬
液を試製し、試験例１と同様に試験を行い、表６に示す
結果を得た。 [Test Example 3] 3-iodo-2-propynyl butyl carbamate (A
-1) and 1,4-bis- (2-ethylhexyl) -sulfo-sodium succinate (B) were used, trial formulations of the chemical solutions shown in Table 5 were carried out, and the same test as in Test Example 1 was conducted. The results shown in Table 6 were obtained.
〔試験例４〕 2,3,3−トリヨードアリルアルコール(A-3)と1,4−ビス
−（２−エチルヘキシル）−スルホ−コハク酸ナトリウ
ム(B)を使用し、表７に示した処方の薬液を試製し、試
験例１と同様に試験を行い、表８に示す結果を得た。 [Test Example 4] 2,3,3-triiodoallyl alcohol (A-3) and 1,4-bis- (2-ethylhexyl) -sodium sulfo-succinate (B) were used and shown in Table 7. A drug solution having a prescription was sampled and tested in the same manner as in Test Example 1, and the results shown in Table 8 were obtained.
〔試験例５〕 ３−ブロモ−2,3−ジヨード−２−プロペニルエチルカ
ルボナート(A-2)と、1,4−ビス−（２−エチルヘキシ
ル）−スルホ−コハク酸ナトリウム(B)を使用し、表９
に示した処方の薬液を試製し、試験例１と同様に試験を
行い、表１０に示す結果を得た。 [Test Example 5] Using 3-bromo-2,3-diiodo-2-propenylethyl carbonate (A-2) and 1,4-bis- (2-ethylhexyl) -sulfo-succinate sodium (B) Table 9
A drug solution having the formulation shown in was prepared as a trial and tested in the same manner as in Test Example 1, and the results shown in Table 10 were obtained.
〔試験例６〕 パラ−クロロフェニル−３−ヨードプロパルギルホルマ
ール(A-4)と、1,4−ビス−（２−エチルヘキシル）−ス
ルホ−コハク酸ナトリウム(B)を使用し、表１１に示す
処方の薬液を試製し、試験例１と同様に試験を行い、得
られた結果を表１２に示した。 [Test Example 6] Para-chlorophenyl-3-iodopropargylformal (A-4) and 1,4-bis- (2-ethylhexyl) -sodium sulfo-succinate (B) were used, and the formulations shown in Table 11 were used. The chemical solution of (1) was trial-produced, and the same test as in Test Example 1 was conducted. The obtained results are shown in Table 12.
次に本発明の防カビ・防腐の若干の製剤例をあげるが、
配合量、補助剤の種類等は大幅に変えうるものであるこ
とは言うまでもない。（文中、単に部とあるのは全て重
量部をあらわす。） 製剤例１． 乳 剤 化合物Ａ−２ １０部及び化合物Ｂ １０部をジメチル
ホルムアミド４０部に溶解させ、キシレン５０部および
ポリオキシエチレンノニルフエニルエーテル１０部を加
えて十分に混合して乳剤を得る。この乳剤は用時適量の
水で希釈して処理すべき木質材料に塗布、浸漬もしくは
スプレー等の方法で使用される他、構造用合板、パーテ
イクルボード等の接着剤混入処理に適用できる。 Next, some formulation examples of antifungal and antiseptic of the present invention will be given.
It goes without saying that the amount of compounding, the type of auxiliary agent, etc. can be changed greatly. (In the text, all parts are simply parts by weight.) Formulation Example 1. Emulsion Compound A-2 (10 parts) and compound B (10 parts) are dissolved in dimethylformamide (40 parts), and xylene (50 parts) and polyoxyethylene nonylphenyl ether (10 parts) are added thereto and mixed sufficiently to obtain an emulsion. This emulsion is used by diluting it with an appropriate amount of water before use and applying it to a woody material to be treated by dipping, spraying, or the like, and can also be applied to the treatment of admixing an adhesive such as structural plywood or particle board.
製剤例２． 油溶性剤 化合物Ａ−２ １部及び化合物Ｂ１部をジメチルホルム
アミド２部に溶解し、ソルベントナフサ９６部を加え油
剤を得た。この油剤は処理すべき木質材料にスプレー、
塗布もしくは浸漬、注入等の方法で使用される。Formulation example 2. Oil-soluble agent Compound A-2 (1 part) and compound B (1 part) were dissolved in dimethylformamide (2 parts), and solvent naphtha (96 parts) was added to obtain an oil agent. This oil is sprayed on the wood material to be treated,
It is used by a method such as coating, dipping or pouring.
製剤例３． 粉 剤 化合物Ａ−２ ２部及び化合物Ｂ２部をアセトン１０部
に溶解し、クレー６８部、タルク３０部を加えて均一に
混合した後、アセトンを蒸発除去して粉剤を得た。Formulation example 3. Dusts 2 parts of compound A-2 and 2 parts of compound B were dissolved in 10 parts of acetone, 68 parts of clay and 30 parts of talc were added and uniformly mixed, and then acetone was removed by evaporation to obtain a powdered product.
製剤例４． 水和剤 化合物Ａ−４ ４０部及び化合物Ｂ２０部、クレー５６
部、ラウリルアルコールスルホン酸ソーダ３部およびポ
リビニルアルコール１部を混合機中で均一に混合し、ハ
ンマーミルで粉砕して水和剤を得た。Formulation example 4. Wettable powder 40 parts of compound A-4 and 20 parts of compound B, clay 56
Parts, 3 parts of sodium lauryl alcohol sulfonate and 1 part of polyvinyl alcohol were uniformly mixed in a mixer and pulverized with a hammer mill to obtain a wettable powder.
製剤例５． 塗 料 化合物Ａ−２ １０部及び化合物Ｂ２０部を、パライト
粉２０部、ビニル樹脂１０部、松脂２５部およびキシレ
ン３５部を均一に混合して塗料を得た。Formulation example 5. Coating material 10 parts of compound A-2 and 20 parts of compound B were uniformly mixed with 20 parts of perlite powder, 10 parts of vinyl resin, 25 parts of pine resin and 35 parts of xylene to obtain a coating material.
製剤例６． エアゾール 化合物Ａ−２ １部及び化合物Ｂ１部、香料0.５部を脱
臭灯油４０部に溶解してエアゾール容器に充填し、バル
ブを装着した後、液化石油ガス５８部を加圧充填してエ
アゾールを得た。Formulation example 6. Aerosol Compound A-2 1 part and compound B 1 part, perfume 0.5 part is dissolved in 40 parts of deodorant kerosene and filled into an aerosol container, and after installing a valve, 58 parts of liquefied petroleum gas is pressurized and filled into the aerosol. Got
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.5 識別記号 庁内整理番号 ＦＩ 技術表示箇所 (Ａ０１Ｎ 41/04 31:04） (Ａ０１Ｎ 41/04 31:14） (Ａ０１Ｎ 47/06 41:04） ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 5 Identification code Office reference number FI technical display location (A01N 41/04 31:04) (A01N 41/04 31:14) (A01N 47/06 41: 04)
Claims (1)
ーバメート、３−ブロモ−２，３−ジヨード−２−プロ
ペニル エチル カーボナート及びパラ−クロロフェニ
ル−３−ヨードプロパルギル ホルマールからなる群
(A)から選ばれた１以上の化合物に１，４−ビス−（２
−エチルヘキシル）−スルホ−コハク酸ナトリウム(B)
を配合したことを特徴とする腐朽菌防除剤。1. A group consisting of 3-iodo-2-propynyl butyl carbamate, 3-bromo-2,3-diiodo-2-propenyl ethyl carbonate and para-chlorophenyl-3-iodopropargyl formal.
One or more compounds selected from (A) have 1,4-bis- (2
-Ethylhexyl) -sodium sulfo-succinate (B)
A rot fungus control agent characterized by being blended with.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61186222A JPH0617284B2 (en) | 1986-08-08 | 1986-08-08 | Microbicide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61186222A JPH0617284B2 (en) | 1986-08-08 | 1986-08-08 | Microbicide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6341405A JPS6341405A (en) | 1988-02-22 |
| JPH0617284B2 true JPH0617284B2 (en) | 1994-03-09 |
Family
ID=16184502
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61186222A Expired - Lifetime JPH0617284B2 (en) | 1986-08-08 | 1986-08-08 | Microbicide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0617284B2 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5035956A (en) * | 1989-08-09 | 1991-07-30 | Safer, Inc. | Lumber product protected by an anti-fungal composition |
| US5045366A (en) * | 1989-08-09 | 1991-09-03 | Safer, Inc. | Method for protecting wood from infestation with sapstain fungi and mold |
| US5736056A (en) * | 1995-04-28 | 1998-04-07 | Betzdearborn Inc. | Method for enhancing biocidal activity |
| US5607597A (en) * | 1995-04-28 | 1997-03-04 | Betzdearborn Inc. | Method for enhancing biocidal activity |
| JP4201165B2 (en) | 2001-09-04 | 2008-12-24 | 住化エンビロサイエンス株式会社 | Industrial mold prevention composition |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61254502A (en) * | 1985-05-02 | 1986-11-12 | Meiji Seika Kaisha Ltd | Fungicidal composition containing triiodoallyl alcohol |
-
1986
- 1986-08-08 JP JP61186222A patent/JPH0617284B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6341405A (en) | 1988-02-22 |
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