Triacontanol

Triacontanol is a plant growth regulator and an animal medicine. Kabal was first isolated from alfalfa in 1933. In 1974, Khanma et al. identified a linear fatty alcohol - 1-triacontanol [CH3(CH2)28CH2OH] from green tea, which was later called "triacontanol". alcohol". In 1975, S.K. Ries discovered triacontanol in the crude extract of alfalfa leaves. This product is often combined with higher fatty acids to form esters and is commonly found in insect wax or plant wax. It is generally extracted from beeswax, bran wax or cane wax, also known as beeswax alcohol.

Customs commodity number: 2905199010; CAS number: 593-50-0

In 1978, the research group of Professor Guo Qizhen of Xiamen University successfully obtained triacontanol crystals from beeswax in China. In 1987, 32 units including the Fujian Academy of Agricultural Sciences and Xiamen University collaborated to study the yield-increasing effects and physiological effects of triacontanol on jasmine and gourd. Both results have reached the international leading level. Then, new areas of application of triacontanol on seaweed were studied. Until 1993, the project "Research on the Application of Plant Growth Regulator Triacontanol Milk Powder on Kelp and Porphyry" passed the appraisal of scientific and technological achievements, and the results reached the international leading level. In 1996, he won the second prize of the National Science and Technology Progress Award. The yield-increasing effect of triacontanol has been affirmed and confirmed. ?

?Based on many years of research results in my country, the use of this product requires attention to methods and conditions. For example, pesticide application concentration must be tested and determined according to different crop varieties, development stages, growth conditions, etc. Otherwise, there is often no yield increase effect, or even yield reduction. The quality of triacontanol is also very important. The product contains higher even-numbered fatty alcohol impurities such as octacosanol that have not been separated and removed. Their presence has an inhibitory effect on the activity of triacontanol. According to the regulations of relevant departments, the content of triacontanol in the product should be ≥95%, and the content of octacosanol should be ≤5%. ?

Toxicity and Residue Status

Triacontanol mostly exists in the form of esters in the waxes of various plants and insects. No toxic effects have been found on humans, animals and beneficial organisms.

At the ninth meeting of my country’s Eighth National Pesticide Registration Review Committee in 2018, the maximum residue limit of triacontanol was exempted in accordance with the “Regulations on Pesticide Registration Information” and other relevant regulations.

According to the U.S. Federal Register, the U.S. Environmental Protection Agency issued a notification on August 16, 2017, exempting 1-Triacontanol from the maximum residue limit in food. It is understood that this exemption application was submitted by CH Biotech R&D, Co., LTD in accordance with the requirements of the US Federal Food, Drug and Cosmetic Act. The US Environmental Protection Agency has conducted a risk assessment on triacontanol in terms of its toxicity, carcinogenicity and other aspects. It was finally concluded that triacontanol has no impact on the health of the general population, infants and children and is therefore exempt from the maximum residue limit requirements for triacontanol in food when used in accordance with label instructions and correct operating practices.

Industrial synthesis

Industrially, dodecanedioic acid is used as raw material, using the alkyl zinc chloride method, or from hexadecene through metathesis reaction and zirconium hydrogenation reaction. This product is synthesized. Beeswax contains more triacontanol. To extract triacontanol from beeswax, it is first heated and extracted with alcohol, then saponified with sodium hydroxide, and then the unsaponifiable product is dissolved in hot amyl alcohol and concentrated hydrochloric acid solution, and then cooled to precipitate triacontanol-based triacontanol. Solid, select a suitable solvent for step-by-step crystallization and activated carbon decolorization to obtain a white scaly crystal product.

Domestic registration status

Since the original drug of triacontanol is almost insoluble in water, the dosage form is one of the important factors that determine the efficacy of the drug. Ries studied triacontanol and first used emulsions. After dissolving the original drug in an organic solvent, a certain amount of emulsifier was added, and then diluted with water to a certain concentration for use. However, the disadvantage of emulsions is that they have poor dispersion and are prone to lactation and precipitation. Later, foreign countries successively proposed acetone dosage forms and colloidal dosage forms of triacontanol, but they were not developed because of the influence of emulsifiers or particle dispersion problems that affected the efficacy.

Domestic units such as Xiamen University and Fujian Academy of Agricultural Sciences have cooperated to develop triacontanol milk powder using CD molecular coating technology, which has made significant progress in triacontanol dosage forms. It has the advantages of stable effects, no deterioration during long-term storage, and convenient storage and transportation. . The application of triacontanol has been developed.

In the 1980s in China, it had a wide application area and was rare among plant growth regulators. Later, due to deviations in promotion, the market shrank. In recent years, it has begun to be promoted again in China. At present, domestic promotion is mainly carried out by Sichuan Guoguang. Currently, it is mostly used to increase the production of mushrooms, resist viruses in vegetables, and increase the production and color of fruit trees such as winter jujubes.

The current domestic registration situation is as follows (as of October 17, 2019)

Currently, there are 17 product registrations for triacontanol***, among which, the technical product registration companies are 2, 15 preparation products, including 6 microemulsion products, 2 wettable powder products, 1 soluble agent, 1 soluble powder, 1 suspending agent, 2 water emulsions, 1 emulsifiable concentrate, water dispersible 1 granule.

Mechanism of action and effects

Triacontanol is effective in many crops (rice, tomatoes, cucumbers, corn, soybeans, barley, wheat, carrots, sugar beets, beans, etc.) and some flowers. The growth and yield are promoted and improved to varying degrees. Laboratory analysis shows that its physiological effects are as follows:

(1) Promote cell division and cell elongation, and increase the fresh weight and number of plant cells. , increase the levels of reducing sugars, free amino acids, soluble nitrogen and reduced nitrogen in plants;

(2) Improve five enzymes in plants: polyphenol oxidase, 6-sulfate gluconate dehydrogenase, The activities of isocitrate dehydrogenase, starch phosphorylase and phosphopyruvate carboxylase promote the conversion of starch into sugar in the body;

(3) It can reduce the inhibition of photosynthesis by molecular oxygen. , enhance photosynthesis and the movement of photosynthetic products, etc.

Plants respond very quickly to triacontanol. After corn seedlings are treated with triacontanol, an increase in dry weight can be measured within 10 minutes; an increase in reducing sugar and free amino acid content can be observed in rice seedlings after 4 minutes of treatment. Such a rapid reaction is related to the rapid absorption and transport of triacontanol in plants. In terms of mechanism, it is speculated that it is related to its activation effect on enzymes and its impact on membrane properties, thus triggering a series of reaction processes.

The figure below is a study of five concentrations of triacontanol (tria) (10–0, 10–8, 10–7, 10–6 and 10–5?M) at 300 das. Effect of total anthraquinone glycoside content and sennoside content of coffee senna leaves (average of three replicates). Error bars (-) show se (Naeem et al., 2010).

In the cultivation of pine mushroom raw materials, adding 3 mg/kg triacontanol can produce mushrooms 3 days earlier than the control, increase the yield by 35.9%, and make the mushrooms larger, and can effectively inhibit the contamination of miscellaneous bacteria.

When using triacontanol on almond trees, the net photosynthetic rate was 1.0ppm>0.5ppm>0.3ppm>0.1 ppm>CK>3.0ppm, indicating that triacontanol promotes photosynthesis as agriculture increases , exhibiting inhibitory effects at high concentrations.

Effects of different concentrations of triacontanol (TA) in greenhouse potted strawberries on the photosynthetic characteristics of strawberries. The results show that TA treatment can significantly improve the photosynthesis of strawberries after 5 days. Compared with the control, strawberry The net photosynthetic rate (Pn) of leaves is promoted at low concentrations (≤0.1 g/L) and inhibited at high concentrations (≥1 g/L).

Differences from brassinolide

The effect of brassinolide foliar spraying on the chlorophyll content of leaves is less than triacontanol, but it maintains a higher chlorophyll level The time is relatively long. This shows that foliar spraying of triacontanol has an immediate effect on promoting chlorophyll content, while the promotion effect of brassinolide is relatively gentle, but the effect is long-lasting, which is more beneficial to delaying leaf aging.

Partial patents

Application technology

?The use of triacontanol is used in various crops. It is currently used in fields and orchards. , which is also commonly used in edible fungi.

Note: When the dosage of triacontanol is large or the purity is not high, it will lead to bent leaf sheaths and root deformities in the seedling stage, and in adult plants, young leaves will curl.

Tips: In production and application, triacontanol still has the problem of unstable effects. The reasons for its instability are as follows:

(1) Three kinds of substances in nature Decanol is ubiquitous, but the application amount is relatively small. The application method and the absorption and utilization rate in the plant will become the key to the effect.

(2) Many compounds widely found in nature, such as octacosanol and phthalate esters, can inhibit the effect of triacontanol. If the purity of triacontanol is increased to 99.79%, the interference of other components can be reduced and its effect can be significantly enhanced; in addition, avoid using containers or pipes made of polyvinyl chloride materials during application, because phthalate ester is This material is a bioplasticizer.

?(3) The water solubility of triacontanol is extremely low. An appropriate formula should be selected. Special attention should be paid to adding auxiliaries to the formula so as not to affect the activity of triacontanol.

Some foreign packaging

Some domestic packaging

Reference materials

1. Bittender, H.C.; Dilley, D.A.; Wert, V. and Ries, S.K.: Environmental Parameters Affecting Dark Response of Rice Seedlings (oryza sativa L) to Triacontanol. Plant Physiol. 61:851-854, 1978

2. M. Naeem , M. Masroor A. Khan & Moinuddin (2012) Triacontanol: a

potent plant growth regulator in agriculture, Journal of Plant Interactions, 7:2, 129-142

3. Li Ling, Xiao Langtao, Tan Weiming ? Modern plant growth regulator technical manual Beijing: Chemical Industry Press? 2018

4. Kong Qinghuan Wenlu Zhu Shourong Zhang Ping Liu Yanwen Wengliang, the yield-increasing effect of triacontanol in pine mushroom raw material cultivation , Jiangsu Agricultural Sciences, 2006, (6): 353-355