JPS6111202B2 - - Google Patents
Info
- Publication number
- JPS6111202B2 JPS6111202B2 JP11933677A JP11933677A JPS6111202B2 JP S6111202 B2 JPS6111202 B2 JP S6111202B2 JP 11933677 A JP11933677 A JP 11933677A JP 11933677 A JP11933677 A JP 11933677A JP S6111202 B2 JPS6111202 B2 JP S6111202B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- captan
- parts
- mixed
- structural formula
- 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
- 230000000887 hydrating effect Effects 0.000 claims description 7
- 230000000087 stabilizing effect Effects 0.000 claims description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- -1 alkaline earth metal salt Chemical class 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- UPTVJAJPBGIRLZ-UHFFFAOYSA-N 2-(trichloromethylsulfanyl)-3a,4,5,7a-tetrahydroisoindole-1,3-dione Chemical compound C1CC=CC2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C21 UPTVJAJPBGIRLZ-UHFFFAOYSA-N 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 229940126062 Compound A Drugs 0.000 description 15
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 15
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 10
- 239000005745 Captan Substances 0.000 description 10
- 229940117949 captan Drugs 0.000 description 10
- 240000008067 Cucumis sativus Species 0.000 description 5
- 241000221785 Erysiphales Species 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- 238000009472 formulation Methods 0.000 description 3
- 241000222199 Colletotrichum Species 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000008186 active pharmaceutical agent Substances 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 229940088679 drug related substance Drugs 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- 235000009849 Cucumis sativus Nutrition 0.000 description 1
- 241000317981 Podosphaera fuliginea Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
本発明は構造式
であらわされるS−ノルマル−ブチルS′−パラ−
ターシヤリ−ブチルベンジルN−3ピリジルジチ
オカ−ボイミデート(以下化合物Aと略記する)
と構造式
であらわされるN−トリクロロメチルチオテトラ
ヒドロフタルイミド(キヤプタンと略記する)と
の混合水和剤において、化合物Aの分解を防止
し、その品質を長期間安定に保持する方法に関す
るものである。
化合物Aは果樹、蔬菜類のうどんこ病に卓効を
有する殺菌剤であるが、抗菌スペクトルが狭く抗
菌スペクトルの広いキヤプタンとの混合剤の製剤
が望まれるが、キヤプタンと混合すると化合物A
〓〓〓
は非常に不安定になり実用に供し得ない。
本発明者らは該混合水和剤における化合物Aの
安定化について種々研究を重ねた結果、炭酸、リ
ン酸、ホウ酸、ケイ酸等弱酸のアルカリもしくは
アルカリ土類金属塩またはカルシウムもしくはマ
グネシウムの酸化物または水酸化物の一種または
二種以上を配合することによりキヤプタンの安定
性を損なうことなく化合物Aの分解を長期にわた
り防止し安定化の目的を達し得ることを見出し、
本発明を完成するに至つた。
本発明におけるこれら添加剤の添加量は2〜5
%の範囲で充分であるが、必らずしもこれに限定
されるものではない。
以下実施例をあげて本発明の方法および効果を
詳細に説明するが、本発明の内容はこれらに限定
されるものではない。
なお、部は重量部をあらわす。
実施例 1
化合物A原体6部、キヤプタン原体67部、添加
剤5部、ハイマールT−450(松本油脂製界面
活性剤)5部、トクシールGu−N(徳山曹達
製ホワイトカーボン)17部を混合したのち微粉砕
して化合物A・キヤプタン(5%+60%)混合水
和剤を得る。この水和剤を密栓付ガラス瓶に入れ
て40℃の恒温器中に1ケ月間保存したのち、化合
物A、キヤプタンの含量を分析し初期含量に対す
る残存率を求めた。得られた結果を第一表に示
す。
The present invention is based on the structural formula S-normal-butyl S'-para-
Tertiary-butylbenzyl N-3 pyridyl dithiocarboimidate (hereinafter abbreviated as compound A)
and structural formula The present invention relates to a method for preventing the decomposition of compound A and stably maintaining its quality for a long period of time in a mixed hydrating powder with N-trichloromethylthiotetrahydrophthalimide (abbreviated as captan) represented by the formula. Compound A is a fungicide that is highly effective against powdery mildew on fruit trees and vegetables. However, it is desired to formulate a mixture with Captan, which has a narrow antibacterial spectrum and a broad antibacterial spectrum. However, when mixed with Captan, Compound A
〓〓〓
becomes extremely unstable and cannot be put to practical use. As a result of various studies conducted by the present inventors regarding the stabilization of Compound A in the mixed wettable powder, we found that the oxidation of alkali or alkaline earth metal salts of weak acids such as carbonic acid, phosphoric acid, boric acid, and silicic acid, or of calcium or magnesium. They have discovered that by blending one or more compounds or hydroxides, it is possible to prevent the decomposition of Compound A over a long period of time without impairing the stability of Captan, thereby achieving the purpose of stabilization.
The present invention has now been completed. The amount of these additives added in the present invention is 2 to 5
% range is sufficient, but is not necessarily limited to this range. The method and effects of the present invention will be explained in detail below with reference to Examples, but the content of the present invention is not limited thereto. Note that parts represent parts by weight. Example 1 6 parts of Compound A raw material, 67 parts of Captan raw material, 5 parts of additives, 5 parts of Hymar T-450 (surfactant manufactured by Matsumoto Yushi), and 17 parts of Toxil Gu-N (white carbon manufactured by Tokuyama Soda). After mixing, the mixture is pulverized to obtain a compound A/captan (5%+60%) mixed wettable powder. This hydrating powder was placed in a glass bottle with a stopper and stored in a thermostat at 40°C for one month, and then the contents of Compound A and Captan were analyzed to determine the residual rate relative to the initial content. The results obtained are shown in Table 1.
【表】【table】
【表】
第一表に示したとおり、本発明による化合物A
の安定化効果は著しいことがわかる。
またこれら上記処方による各製剤品について次
のような方法でキユウリうどんこ病および炭そ病
に対する防除効果を検討した。
キユウリうどんこ病防除効果試験
直径9cmの素焼鉢に栽培したキユウリ(品種:
加賀節成)が3〜4葉期に達した時各供試製剤を
水で希釈し1鉢当り10mlの割合で散布した。散布
2日後にウリ類うどんこ病菌(Sphaerotheca
fuliginea)の胞子液を噴霧接種した。さらに14日
後発病状態を下記の6段階にわけて調査し発病数
を下式により算出した。[Table] As shown in Table 1, Compound A according to the present invention
It can be seen that the stabilizing effect of is remarkable. Furthermore, the control effects of each of the above-mentioned formulations on cucumber powdery mildew and anthracnose were examined using the following method. Kiyu cucumber powdery mildew control efficacy test Ki cucumber grown in clay pots with a diameter of 9 cm (variety:
When the plants (Kaga Setsei) reached the 3-4 leaf stage, each test preparation was diluted with water and sprayed at a rate of 10 ml per pot. Two days after spraying, cucurbit powdery mildew fungus (Sphaerotheca
fuliginea) was inoculated by spraying. Furthermore, the state of disease onset after 14 days was investigated in the following 6 stages, and the number of disease onsets was calculated using the following formula.
【表】
キユウリ炭そ病防除効果試験
直径9cmの素焼鉢に栽培したキユウリ(品種:
相模半日)が3〜4葉期に達した時、各供試薬剤
を水で希釈し1鉢当り10mlの割合で散布した。散
布1日後キユウリ炭そ病菌(Colletotrichum
〓〓〓〓
lagenarium)の胞子液を噴霧接種した。さらに
7日後発病状態を上記のごとく6段階にわけて調
査し、発病度を上記式により算出した。結果を第
二表に示す。
希釈培率はいずれの試験においても製剤品の
5000倍である。したがつて有効成分濃度は(化合
物A10ppm+キヤプタン120ppm)である。[Table] Anthracnose control effect test on cucumbers (variety:
When the plants (Sagami half-day) reached the 3-4 leaf stage, each test chemical was diluted with water and sprayed at a rate of 10 ml per pot. One day after spraying, Colletotrichum bacterium (Colletotrichum)
〓〓〓〓
The spore liquid of Lagenarium was inoculated by spraying. Furthermore, the state of onset of disease after 7 days was investigated in 6 stages as described above, and the severity of disease was calculated using the above formula. The results are shown in Table 2. The dilution rate was
It is 5000 times more. Therefore, the active ingredient concentration is (10 ppm of compound A + 120 ppm of captan).
【表】【table】
【表】
第二表に示したとおり本発明による水和剤は40
℃1ケ月保存後でも生物効果の低下はみられず安
定化効果が著しいことがわかる。
実施例 2
化合物A原体6部、キヤプタン原体67部、添加
剤0.5〜10部、ハイマールT−450(前記)5部、
残部をトクシールGu−N(前記)で混合したの
ち微粉砕して化合物A・キヤプタン(5%+60
%)混合水和剤を得る。この水和剤を密栓付ガラ
ス瓶に入れて40℃恒温器中に1ケ月保存したのち
化合物A、キヤプタンの含量を分析し初期含量に
対する残存率を求めた。得られた結果を第三表に
示す。[Table] As shown in Table 2, the hydrating agent according to the present invention has 40
Even after storage at ℃ for 1 month, no decrease in biological effects was observed, indicating a remarkable stabilizing effect. Example 2 6 parts of Compound A drug substance, 67 parts of Captan drug substance, 0.5 to 10 parts of additives, 5 parts of Hymar T-450 (above),
The remainder was mixed with Tokusil Gu-N (above) and finely pulverized to form Compound A Captan (5% + 60%).
%) to obtain a mixed hydrating agent. This hydrating powder was placed in a glass bottle with a stopper and stored in a thermostat at 40° C. for one month, and then the contents of Compound A and Captan were analyzed to determine the residual percentage relative to the initial content. The results obtained are shown in Table 3.
【表】
〓〓〓〓
[Table] 〓〓〓〓
【表】
第三表に示したとおり配合する添加剤は2〜5
部の範囲で充分であり、これらは化合物Aの安定
化効果が著しいことがわかる。
またこれら上記処方による各製剤品について、
実施例1と同様の方法でキユウリうどんこ病およ
び炭そ病に対する防除効果を検討した。得られた
結果を第四表に示す。[Table] As shown in Table 3, the additives to be blended are 2 to 5.
It can be seen that the stabilizing effect of Compound A is remarkable. In addition, regarding each of the formulations based on the above formulations,
The control effect on cucumber powdery mildew and anthracnose was examined in the same manner as in Example 1. The results obtained are shown in Table 4.
【表】
第四表に示したとおり添加剤を2部以上配合し
た水和剤は40℃1ケ月後でも生物効果の低下はみ
られず安定化効果が著しいことがわかる。
〓〓〓〓
[Table] As shown in Table 4, it can be seen that the biological effects of hydrating powders containing two or more parts of additives do not decrease even after one month at 40°C, and the stabilizing effect is remarkable. 〓〓〓〓
Claims (1)
ターシヤリ−ブチルベンジルN−3ピリジルジチ
オカ−ボイミデートと 構造式 であらわされるN−トリクロロメチルチオテトラ
ヒドロフタルイミドとの混合水和剤において、弱
酸のアルカリもしくはアルカリ土類金属塩または
カルシウムもしくはマグネシウムの酸化物または
水酸化物の一種または二種以上を配合することを
特徴とするS−ノルマルブチルS′−パラターシヤ
リ−ブチルベンジルN−3ピリジルジチオカ−ボ
イミデートの安定化方法。[Claims] 1. Structural formula S-normal-butyl S'-para-
Tertiary-butylbenzyl N-3 pyridyl dithiocarboimidate and structural formula A mixed hydrating agent with N-trichloromethylthiotetrahydrophthalimide represented by is characterized by containing one or more of an alkali or alkaline earth metal salt of a weak acid or an oxide or hydroxide of calcium or magnesium. A method for stabilizing S-n-n-butyl S'-paratertiary-butylbenzyl N-3 pyridyldithioca-boimidate.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP11933677A JPS5452726A (en) | 1977-10-03 | 1977-10-03 | Stabilization of pesticide |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP11933677A JPS5452726A (en) | 1977-10-03 | 1977-10-03 | Stabilization of pesticide |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5452726A JPS5452726A (en) | 1979-04-25 |
JPS6111202B2 true JPS6111202B2 (en) | 1986-04-01 |
Family
ID=14758947
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP11933677A Granted JPS5452726A (en) | 1977-10-03 | 1977-10-03 | Stabilization of pesticide |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS5452726A (en) |
-
1977
- 1977-10-03 JP JP11933677A patent/JPS5452726A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS5452726A (en) | 1979-04-25 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JPH01157971A (en) | Stabilized isothiazolone composition | |
KR0149025B1 (en) | Concentrated aqueous solution of glutaraldehyde and 1,2-benzisothiazolin-3 one | |
RU2273637C2 (en) | Derivatives of mepiquate borate, methods for their preparing, electrochemical method for preparing n,n-dimethylpiperidinium, suspension concentrate possessing plant growth-regulating effect | |
NO144476B (en) | PRESSURE TO SELECT A SURFACE PRINT. | |
AU5808200A (en) | Solvates of pymetrozine | |
ES8604711A1 (en) | Pyridine, pyrazine and pyrimidine derivatives and their use as fungicides. | |
JPS6111202B2 (en) | ||
EP0141844B1 (en) | Fumigation methods and compositions | |
IE840495L (en) | Method of producing standardized iodophors | |
US4402853A (en) | Stable peroxide composition and method of preparation thereof | |
CN112868661B (en) | Bactericidal composition and application thereof | |
JPS60132908A (en) | Stabilized sterilizing composition based on phosethyl aluminum and copper compound | |
US3928606A (en) | Fungicidal composition containing diisopropyl 3-nitrophthalate and N-tridecyl-2,6-dimethylmorpholine | |
KR920003215B1 (en) | Oxygen generating agent | |
JPS6051102A (en) | Stabilized fungicidal composition | |
RU2025131C1 (en) | Solid disinfectant | |
US3814803A (en) | Stabilized pesticidal compositions containing alkyl dinitrophenyl esters | |
JP2627291B2 (en) | Stabilized insecticide / bactericidal pesticide composition | |
EP0988791B1 (en) | Method for reducing deflagration of azinphos-methyl | |
EP0337503B1 (en) | Fumigation methods and compositions | |
US1063313A (en) | Insecticide. | |
US2943014A (en) | Process for preparing sanitizing compositions | |
US10617136B2 (en) | Calcium oxide compound with high purity | |
JPH07118108A (en) | Flower-thinning agent for apple | |
JPH0789907A (en) | Solidification of didecyl dimenthylammonium chloride |