Studies on the effect of phthalimido methyl-O,O-dimethyl-phosphorodithioate (Imidan) and its possible metabolites on the growth of rice plant

Phthalimido methyl-O,O-dimethyl phosphorodithioate (Imidan)과 그의 대사물질(代謝物質)이 수도(水稻) 생육(生育)에 미치는 영향(影響)에 관(關)한 연구(硏究)

This experiment was conducted to investigate the effet of phthalimido-methyl-O,O-dimethyl-phosphorodithioate (Imidan) known as an acaricide and its possible metabolic products on the growth of plant, when sprayed on the leaves of rice plant. The results are summarized as follows. 1) Possible metabolic products of Imidan, the following compounds were synthesized or recrystallized for the present experiment a) N-Hydroxymethyl phthalimidem b) Phthalimide c) Phthalamidic acid d) Phthalic acid e) Anthranilic acid f) p-Amino benzoic acid g) p-Hydroxy benzoic acid h) Benzoic acid 2) Among the above materials, a), c), d), e), and Imidan were dissolved in a buffer solution respectively to be 10 and 20 p.p.m. and tested with the wheat coleoptile straight growth method. According to the results, Imidan inhibited the growth of coleoptile in both 10 and 20 p.p.m., whereas the others showed much better growth than the control, especially phthalamidic acid in 10 p.p.m. It appears that Imidan itself inhibits the coleoptile growth, whereas the metabolites derived from Imidan through various metabolisms, including hydrolysis in plant tissues show growth-regulating activity. (refer: Table 1, Fig. 1) 3) 20, 100 and 200 p.p.m. solutions of Imidall emulsion in xylene f·ere prepared. The lengths of shoot and root of rice seeds germinated on the re-respective media were measured after 12 days. The data showed that root was much more elongated in Imidan 20 p.p.m., whereas shoot in Imidan 100 p.p.m., respectively, than in the xylene control. An interesting finding was that xylene used as solvent had a tendency to inhibit seriously the root growth of rice seed. (refer: Table 2,5). 4) The emulsions of concentrations in 10, 25, 50 and 100 p.p.m's of control, Imidan, N-hydroxy methyl phthalimide, anthranilic acid, and phthalmide, respectively, were sprayed twice on the rice plant on pot. After a certain period of time lengths of rice culms were measured, showing that plots treated with Imidan and N-hydroxy methyl phthalimide exhibited much more growth than those of control and the others. 5) Loaves and stems of rice plant were sampled and extracted with dried acetone at the intervals of 3-, 5-, 7-, and 14 days after treated with Imidan 250 p.p.m. emulsion. This sample extracted with acetone was purified by means of prechromatographic purification method with acetonitrile and paperchromatographed to detect the following metabolic products. Imidan (Rf: 0.97-0,98), N-hydroxy-methyl phthalimide (Rf: 0.87) phthalimide (Rf: 0.86-0.87), phthalamidic acid (Rf: 0.13-0.14), phthalic acid (Rf: 0.02-0.03), benzoic acid (Rf: 0.42-0.43), p-amino benzoic acid or p-hydroxy benzoic acid (Rf: 0.08-0.09), and unidentified compounds (Rf: 0.73, 0.59, 0.33, 0.23. 0.07). In addition, in the early stages, such as 3- and 5 days nonhydrolyzed Imidan and its first hydrolytic product, N-hydroxymethyl phthalimide were detected in relatively large amounts, whereas in the last stages of 7- and 14 days due to further decomposition, the afore-mentioned two materials were reduced in the amount and p-hthalic, phthalamidic, benzoic, and p-Hydroxy benzoic, or p-Amino benzoic acids were detected in a considerably large amount. It is, therefore, believed that most of Imidan applied to the leaves of rice plant may be decomposed within almost 14 days. In the light of above observations it is considered that Imidan itself is not involved in plant growth regulating activity, whereas various phthaloyl derivatives produced in the course of metabolism (namelr, enzymic action) in plant tissues may have such effect.

acaricide로 알려진 phthalimidomethyl O,O-dimethyl phosphorodithioat (Imidan)을 수도(水稻)에 살포(撒布)했을 때 Imidan과 그 대사물질(代謝物質)이 식물(植物)의 생육(生育)에 미치는 영향(影響)을 연구(硏究)하기 위하여 본(本) 실험(實驗)을 하였으며 이의 결과(結果)를 요약(要約)해 보면 다음과 같다. (1) Imian의 대사물질(代謝物質)로 예상(豫想)되는 다음의 8가지 화합물(化合物)을 합성(合成) 또는 정제(精製)하여 공시약제(供試藥劑)로 사용(使用)하였다. (a) N-Hydroxy methyl phthalimide (b) Phalimide (c) Phthalamdic acid (d) Phthalic acid (e) Anthranilic acid (f) p-amino benzoic acid (g) p-hydroxu benzoic acid (h) Benzoic acid (2) 상기(上記) 물질중(物質中)에서 (a),(c),(d),(e)와 Imidan의 각(各) 10 ppm과 20 ppm 의 Buffer Solution 을 만들어 밀 종자(種子)를 가지고 coleoptile straight growth test를 해 본 결과(結果) Imidan 은 10 ppm 과 20 ppm에서 모두 control 보다 생장(生長)의 촉진효과(促進?果)를 보였으며 기중(其中) phthalamidic acid 10 ppm 이 가장 좋은 성적(成績)을 보였다. 이것으로 보아 Imidan 자체(自體)는 생장(生長) 억제(抑制)의 효과(?果)를f 보이나 이것이 일단(一但) 생체내(生體內)에서 가수분해(加水分解)를 비롯한 각종(各種) 대사작용(代謝作用)을 받으면 그 대사산물(代謝産物)이 식물생장(植物生長)을 촉진(促進)하는 효과(?果)를 보이는 것 같다. (Table 1, Fig. 1 참조(參照)) (3) xylene을 용매(溶媒)로 하여 Imidan 유제(乳劑)를 만들고 이것을 희석(稀釋)하여 20 ppm, 100 ppm 및 200 ppm 의 각(各) 농도(濃度) 유화액(乳化液)을 조제(調製)한 후 이것을 배지(培地)로 하여 수도종자(水稻種子)를 발아(發芽)시킨 후 12 일(日)에 shoot와 root의 길이를 측정(測定)하였다. 이의 결과(結果)를 보면 root는 Imidan 20 ppm에서, shoot 는 Imidan 100 ppm에서 모두 xylene만의 유제구(乳劑區)인 control 보다 좋은 효과(?果)를 보였으며 여기에서 흥미(興味)있는 것은 용매(溶媒)로 사용(使用)된 xylene은 수도종자(水稻種子) 뿌리의 발육(發育)에 심(甚)한 억제효과(抑制效果)를 보이는 것 같다. (Table 2, Table 5 참조(參照)) (4) 벼를 pot에 심고 2회(回)에 걸쳐 control, Imidan, N-hydroxy methyl phthalimide, anthranilic acid 및 phthalimide의 10, 25, 50, 100 ppm 농도(濃度)의 각(各) 유제(乳劑)를 살포하고 일정기간후(一定期間後) 생육상(生育相)을 조사(調査)하였더니 Imidan 구(區)와 N-hydroxy methyl phthalimide 구(區)가 control 보다 좋은 성적(成績)을 보였다. (5) Imidan 250 ppm 유제(乳劑)를 수도엽면(水稻葉面)에 살포(撒布)하고 3 일(日), 5 일(日), 7 일(日) 및 14일후(日後)에 일정량(一定量)의 엽경(葉莖)을 채취(採取)하여 acetone으로 추출(抽出)k고 acetonitrile을 가지고 prechromatographic piriication 을 거쳐 paper chromatography에 의(依)하여 다음과 같은 대사물질(代謝物質)을 검출(檢出)하였다. Imidan $(Rf:\;0.97{\sim}0.98)$, N-hydroxy methyl phthalimide (Rf: 0.87), phthalimide $(Rf:\;0.86{\sim}0.87)$, phthalamidic acid $(Rf:\;0.13{\sim}0.14)$, phthalic acid $(Rf:\;0.02{\sim}0.03)$, benzoic acid $(Rf:\;0.42{\sim}0.43)$ 및 p-amino benzoic acid 또는 p-hydroxy benzoic acid $(Rf:\;0.08{\sim}0.09)$와 Rf=0.73, 0.59, 0.33, 0.23, 0.07의 미지물질(未知物質)을 검출(檢出)하였다. 또한 3일(日), 5일(日) 등(等) 초기(初期)에서는 미분해(未分解)의 Imidan과 최초(最初)의 가수분해(加水分解) 산물(産物)인 N-hydroxy methyl phthalimide등(等)이 비교적(比較的) 다량(多量)으로 검출(檢出)되었으나 7일(日), 14일(日) 등(等) 후기(後期)에는 생체내(生體內)에서 더 많은 분해(分解)를 받아 상기(上記) 이성분(二成分)은 양(量)이 감소(減少)되고 phthalic acid, phthalamidic acid benzoic acid 및 p-hydroxy benzoic acid 또는 p-amino benzoic acid등(等)의 양(量)이 증가(增加)되는 것을 볼 수있었으며 도체상(稻體上)에 살포(撒布)된 Imidan 은 체내(體內)에 흡수(吸收)되어 14일(日)이 경과(經過)되면 대부분(大部分)이 분해(分解)를 받는 것으로 보여진다. 이상(以上)의 결과(結果)로 보아 Imidan은 자체(自體)로서는 식물생장(植物生長) 촉진작용(促進作用)이 없으나 식물체내(植物體內)에서 여러 가지 대사작용(代謝作用)(enzyme의 작용(作用))을 맡아서 각종(各種) phthaloyl 영향(影響)을 주는 것으로 생각(生覺)된다.