Application of N-(1-ethynylcyclohexyl)amide of O,O-diethyl-phosphoric acid as a growth stimulant for vegetable crops

Aplicação da amida N-(1-etinilciclohexil) do ácido O,O-dietilfosfórico como estimulante do crescimento de culturas hortícolas

Abstract

This paper examines the effect of N-(1-ethynylcyclohexyl)amide O,O-diethylphosphoric acid (BA-4) on seed germination, growth and yield of the agricultural crops (carrot, beetroot, potato). As a result, seed germination in the concentrations of 0.001 and 0.0001% of BA-4 has increased by 7.0 and 19.0%, compared to the control. The results of the laboratory studies have shown that the treatment of with the BA-4 (0.0001% solution) has increased the seed germination energy by 11.0 and 17.0%, respectively. The HAU standard (0.06%) has increased the germination energy by 9.0% and germination by 10.0%. The results of the laboratory studies have shown that the use of BA-4 for treating the tubers has increased the number of awakened buds by 43.0% (0.001%) and 60.0% (0.0001%), compared to the control. When using BA-4 in the concentration of 0.001%, the carrot yield has increased by 3.5 t/ha or 15.9%, and in the concentration of 0.0001% - by 5.0 t/ha or 22.7%. When beetroot seeds were treated with the BA-4 preparation at a 0.0001% concentration, the yield increase compared to the control was 6.3 t/ha or 24.2%. The potato yield has increased from the use of BA-4 in concentration of 0.001% by 4.3 t/ha or 18.9%, compared to the control; in the concentration of 0.0001% - by 7.3 t/ha or 32.2%. The achieved results of increasing the yield of BA-4 are an effective stimulation of plant growth and development, contribute to an increase in the yield and ensure the compliance with the agricultural crop indicators.

Keywords:
plant growth regulator; potato; carrot; beetroot; agricultural crop yield

Resumo

Este trabalho examina o efeito da amida N-(1-etinilciclo-hexil) do ácido O,O-dietilfosfórico (BA-4) na germinação, crescimento e rendimento de sementes de culturas agrícolas (cenoura, beterraba, batata). Como resultado, a germinação das sementes nas concentrações de 0,001% e 0,0001% de BA-4 aumentou 7,0% e 19,0%, em relação ao controle. Os resultados dos estudos laboratoriais mostraram que o tratamento com o BA-4 (solução a 0,0001%) aumentou a energia de germinação das sementes em 11,0% e 17,0%, respectivamente. O padrão HAU (0,06%) aumentou a energia germinativa em 9,0% e a germinação em 10,0%. Os resultados dos estudos laboratoriais mostraram que o uso de BA-4 para o tratamento dos tubérculos aumentou o número de gemas ativadas em 43,0% (0,001%) e 60,0% (0,0001%), em comparação com o controle. Ao utilizar BA-4 na concentração de 0,001%, o rendimento da cenoura aumentou 3,5 t/ha ou 15,9%, e na concentração de 0,0001% - 5,0 t/ha ou 22,7%. Quando as sementes de beterraba foram tratadas com o preparado BA-4 na concentração de 0,0001%, o aumento de produtividade em relação ao controle foi de 6,3 t/ha ou 24,2%. O rendimento da batata aumentou a partir do uso de BA-4 na concentração de 0,001% em 4,3 t/ha ou 18,9%, em relação ao controle; na concentração de 0,0001% - em 7,3 t/ha ou 32,2%. Os resultados obtidos no aumento da produtividade do BA-4 são um estímulo efetivo ao crescimento e desenvolvimento das plantas, contribuindo para o aumento da produtividade e garantindo o cumprimento dos indicadores das culturas agrícolas.

Palavras-chave:
regulador de crescimento vegetal; batata; cenoura; beterraba; rendimento das culturas agrícolas

1. Introduction

Plant growth regulators (PGR) are a type of pesticide, which controls the growth and development of plants, increases their resistance to diseases, drought, salinity and frost, optimizes the absorption of fertilizers, increases crop yields and improves the quality of the products (Feng et al., 2023). They are produced either from natural resources or from synthetic substances (Kumari et al., 2018), which have found a wide application in agriculture (Small and Degenhardt, 2018), horticulture (Kondo et al., 2022) and other areas.

The use of plant growth regulators in agriculture based on pesticides, antidotes, seed dressings, bactericides, insecticides, acaricides, nematicides and zoocides is known.

The disadvantage of using plant growth regulators is that usually for their use it is necessary to take into account the fact, that each of them is created to stimulate the growth, development and increase the productivity of certain crops at appropriate doses, times and methods of application. At the same time, the work on the preparation of seed material is unsatisfactory. Due to financial difficulties, the costs of seed processing have been reduced to a minimum (Melnikov et al., 1995).

The closest in technical essence to the declared object is heteroauxin, which is a sodium or potassium salt of β-indoleacetic acid (Melnikov and Baskakov, 1962).

The use of growth accelerators in agro-industry can play a key role in ensuring the sustainable development of the food sector. Certain plant growth stimulants are known to be effective in crop production within the agro-industrial complex (Kolbin and Ikrina, 2005; Muromshev, 1987).

It is known that the use of phosphorus-containing compounds is of practical importance as activators of the plant life processes. It has been established that the nature of the substitution at the nitrogen atom of phosphonopiperidoles has a significant effect on the activity of the phosphorus-containing compounds of the the piperidine series; unsubstituted phosphonopiperidoles are less active than their N-alkyl analogues (Nifantiev, 1971; Dzhiembaev, 2003).

PGR play an important role in managing plant growth and development. They stimulate metabolic processes and promote more efficient absorption of nutrients, which improves the condition of plants and increases the crop yields. However, their mechanisms of action on stimulating plant growth are different. Plant growth regulators are an important component in agriculture (Gianfagna, 1995).

They improve plant growth and health by stimulating the natural processes in small amounts rather than directly controlling the plant growth (Colla and Rouphael, 2015).

Plant growth regulators are used in small doses and contain fewer impurities, compared to the conventional fertilizers (Gupta and Van Staden, 2021).

Therefore, the risk of toxicity and hazard to humans and the environment remains minimal (Kisvarga et al., 2022). PGRs have significant market potential and play a key role in increasing global crop production by helping to reduce the impact of environmental stress and improve the crop yields. Their use has become an integral part of modern agriculture, contributing to its sustainable development. Thanks to PGRs, the crop yields can be increased by 10-15 million tons annually (Rademacher, 2015).

In addition, PGRs can reduce the need for excessive use of fertilizers and pesticides, which helps to preserve the environment (Shah et al., 2023).

The agricultural progress, being a part of the modern model of agriculture, forces us to look for innovative methods of intensifying agricultural production and improving the quality indicators, while reducing the negative impact on the environment (Zhumanova et al., 2024; Baitasheva et al., 2024).

Indole-3-acetic acid (IAA) is a heterocyclic monocarboxylic acid compound and is the predominant natural auxin. Its structure was identified in 1934. After that, agrochemists have developed a large number of derivatives around the indole skeleton and assessed their auxin activity (Li et al., 2025; Lavy and Estelle, 2016; Teale et al., 2006; Woodward and Bartel, 2005; Zhang et al., 2022).

Comparison with other well-known representatives of this class, such as amidophosphates (Hong-wu et al., 2002), alkylphosphonates (Nadiveedhi et al., 2021), phosphorus-based regulators (Zhang et al., 2023), and phosphonate esters (Zhang et al., 2024), suggests that the unique structural features of BA-4 may contribute to its enhanced biological activity.

2. Materials and Methods

2.1. The laboratory experiment

The optimal growth-activating concentrations of the new compound were determined in the laboratory conditions: the effect of the preparation on the germination energy and viability of carrot and seeds and on the awakening of potato tuber buds. The concentration of the preparation varied from 1.0 up to 0.0001%. The optimal active concentrations of the preparation were further studied on the growth, development and yield of crops in the field conditions.

Carrot and seeds were soaked in freshly prepared solutions of the BA-4. Carrot and beet seeds soaked in water served as a control; a 0.06% solution of HAU (heteroauxin) was used as a standard. The seeds were germinated in Petri dishes in a thermostat, there were six replicates (repetitions). The sprouted seeds of carrots and were counted in 2 periods: the first - 5 days after the treatment (to determine the germination energy), the second - after 10 days (to determine the seed germination). The effect of the preparation on bud awakening was studied on the potato tubers. For potatoes, seeds soaked in the Extrasol solution (10.0%) served as a standard. The potato tubers were sprouted in boxes in wet sawdust, 20 tubers were sprouted in each repetition, the repetition was sixfold. The awakened buds were counted after 10 and 15 days (Miedema, 1973).

2.2. The field experiment

The established optimal concentrations of the preparation were further studied in the field for their effect on the growth, development and yield of crops. To conduct the study in the field, the seeds were treated with freshly prepared solutions of the BA-4; untreated seeds served as a control, while seeds treated with the HAU solution (0.06%) served as a standard in the experiments with carrot, beetroot and the trubers soaked in a 10.0% Extrasol solution served as a standard in the experiments with potato (Figure 1).

Figure 1
Field layout of the experiment.

The achieved technical outcome included an increase in the yield of agricultural crops (carrot, beetroot and potato), promotion of their subsequent growth and development, as well as a marked decrease in both crop loss and toxicity. Throughout the growing season, biometric assessments were performed on 20 typical plants, focusing on parameters such as plant height, leaf number, and fruit weight. Field productivity was evaluated separately for each experimental plot. Statistical analysis of the efficiency indicators was conducted using the analysis of variance method, following the methodology proposed by B. A. Dospekhov (Dospehov, 1985). Modifications in plant morphology were observed as a result of seed treatment (Nurmahanova et al., 2024; Starič et al., 2020). Census plots for carrot and beetroot, each measuring 10 m², for potatoes 25 m² were established in four replications. In the experiments, the phenological observations were carried out for each variant, taking into account the sowing date, single and mass shoots, the beginning of the formation of 2-3 and 6-8 leaves (Alexander, 2020; Bierhuizen, 1981; University of Idaho Extension, 2019). Work has been carried out to control the influence of a chemical substance that affects the growth and development of plants on the activity of using carrot and beetroot as growth accelerators in the agro-industrial complex. N-(1-ethynylcyclohexyl)amide of O,O-diethylphosphoric acid with the code BA-4 and the following formula was proposed as a growth stimulator for carrot and beetroot for the technical result.

2.3. Synthesis, structure and determination of the BA-4 preparation

The chemical structures of the active compound BA-4 were determined by the nuclear magnetic resonance (NMR) analysis. ¹H NMR and ¹³C NMR spectra were obtained in Chloroform-d, using a Bruker AVANCE III 600 spectrometer (Bruker Corporation, Germany) at 600 MHz for the ¹H NMR spectra and 125 MHz for the ¹³C NMR spectra, using Chloroform-d as an internal standard. The IR spectra were recorded on a Bruker ALPHA Fourier spectrometer in the range of 400-4000 cm^-1. The samples were analyzed as a pellet in KBr. The microwave synthesis was performed in a MAS-II Plus microwave reactor (Sineo, China). The X-ray structural data were obtained on a Bruker D8 QUEST automatic diffractometer with a PHOTON II CCD detector [graphite monochromator, λ(MoK_α) = 0.71073 Å, ω-scanning] (Bruker Corporation, Germany). The melting points were determined on a Boetius apparatus. The elemental analysis was performed on a Carlo Erba EA 1108 apparatus (Kuandykova et al., 2023).

N-(1-ethynylcyclohexyl)amide of O,O-diethylphosphoric acid (3). 0.01 mol (1.10 g, 0.92 mL) of diethyl phosphite (2), 0.02 mol (3.08 g, 2.11 mL) of tetrachloride carbon, 0.015 mol (1.52 g, 1.08 mL) of triethylamine, and 0.01 mol of 1-ethynyl-1-aminocyclohexane (1) was placed in a 25 mL open flat-bottomed flask. The reaction was carried out in a MAS-II Plus microwave reactor for 3-5 min. The reaction progress was monitored by the TLC in the benzene-ethanol 10:1 system, Rf = 0.69. After cooling, the solvent was evaporated on a rotary evaporator, the resulting amidophosphate (3) was recrystallized from petroleum ether (40-70 °C). The yield: 2.35 g (91%), white powder, m.p. 50-51°С. The active compound has been a white crystal, which has been easily soluble in water (white powder, m.p. 50-51 °C). The IR spectrum, ν, cm^-1: 3175 (NH), 3229 (≡CH), 2107 (C≡C), 1209 (P=O), 1031 (P-O-C). ¹H NMR (400 MHz, Chloroform-d) δ 4.15–4.08 (m, 4H), 2.93 (d, J = 7.2 Hz, ¹H), 2.40 (s, ¹H), 2.02 (d, J = 5.9 Hz, 2H), 1.62 (dd, J = 20.8, 9.3 Hz, 7H), 1.34 (t, J = 7.1 Hz, 6H). ¹³C NMR (101 MHz, Chloroform-d) δ 51.93 (s, C-1); 39.80 (d, C-2,6); 23.25 (s, C-3,5); 24.21 (d, C-4); 87.44 (d, C-7); 73.48 (s, C-8); 62.59 (s, C-9,11); 61.14 (s, C-10,12). ³¹Р NMR, δ, ppm: 8.00. Anal. Calc. for С₁₂Н₂₂NO₃P, %: С, 55.59; Н, 8.49; N, 5.40; P, 11.96. Found., %: С 55.23; Н 8.53; N 5.66; P 11.54 (Figure 2).

Figure 2
N-(1-ethynylcyclohexyl)amide of O,O-diethylphosphoric acid (3).

3. Results

3.1. Effect of BA-4 on the germination energy and germination capacity of carrot and beetroot seeds and on awakening of the potato tuber buds

3.1.1. Study of the effect of the preparation on the germination energy and germination capacity of carrot and beetroot seeds

The results of the laboratory studies have shown that seed treatment with the preparation with the concentrations of 0.001 and 0.0001%, conventionally called BA-4, increases the germination energy of carrot seeds by 19.0 and 24.0%, compared to the control. Germination of carrot seeds when treated with BA-4 in the concentrations of 0.001 and 0.0001%, increases by 7.0 and 19.0%, compared to the control. The treatment of carrot seeds with the 0.06% solution of HAU (heteroauxin) increases the germination energy by 13.0% and seed germination by 12.0%, compared to the control. The data presented in Table 1 show that the treatment of beetroot seeds in the BA-4 solution of the concentration of 0.001%, increases the germination energy of seeds by 5.0%, germination by 10.0%, in the concentration of 0.0001% - by 11.0 and 17.0%, respectively. The HAU standard (0.06%) increases the germination energy by 9.0% and germination by 10.0%.

Table 1
The effect of a new preparation on the germination energy and seed viability of carrots and beetroot.

	Carrot		Beetroot
Experiment variants	Germination energy (%)	Germination (%)	Germination energy (%)	Germination (%)
Control without the treatment	51.0 ± 0	72.0 ± 0.08	56.0 ± 0.02	78.0 ± 0.03
BA-4 1.0%	-	-	-	-
BA-4 0.1%	53.0 ± 0.26	73.0 ± 0.07	57.0 ± 0.02	81.0 ± 0.04
BA-4 0.01%	56.0 ± 0.13	77.0 ± 0.05	59.0 ± 0.03	86.0 ± 0.02
BA-4 0.001%	70.0 ± 0.09	79.0 ± 0.02	61.0 ± 0.01	88.0 ± 0.03
BA-4 0.0001%	75.0 ± 0.05	91.0 ± 0.04	67.0 ± 0.03	95.0 ± 0.05
1HAU 0.06% (standard)	64.0 ± 0.04	84.0 ± 0.04	65.0 ± 0.03	88.0 ± 0.03

• ¹
  HAU = heteroauxin.

3.1.2. Study of the effect of the preparation on the awakening of the potato tuber buds

The results of the laboratory studies have shown that the treatment of the tubers with BA-4 in the concentration of 0.001% increases the number of the awakened buds, compared to the control by 43.0%; the treatment of the tubers BA-4 in the concentration of 0.0001% increases the number of the awakened buds by 60.0%., compared to the control.

It should be noted that the increase in the number of the awakened buds occurs due to the awakening of the lateral and stem end parts of the tubers, which in the control variant (as usual) have remained unawakened. When potato tubers have been treated with the standard preparation Extrasol in the concentration of 10%, the number of the awakened buds has been by 17.0% higher than in the control (Table 2).

Table 2
The effect of the preparation on the germination of the potato tuber eyes.

	Including
Experiment variants	terminal	lateral	Stem end	Number of sprouted buds	Percentage to control
Control without the treatment	3.0 ± 0.02	0	0	3.0 ± 0.01	100 ± 0.02
BA-4 1.0%	0	0	0	0	0
BA-4 0.1%	3.0 ± 0.01	0	0	3.0 ± 0.01	100 ± 0.01
BA-4 0.01%	3.0 ± 0.03	0	0.7 ± 0.01	3.7 ± 0.02	123 ± 0.02
BA-4 0.001%	3.2 ± 0.01	0	1.1 ± 0.01	4.3 ± 0.01	143 ± 0.02
BA-4 0.0001%	3.2 ± 0.01	0.6 ± 0	1.0 ± 0.01	4.8 ± 0.01	160 ± 0.02
Extrasol (standard), 10%	3.0 ± 0.01	0	0.5	3.5 ± 0.01	117 ± 0.01

3.2. The effect of the BA-4 on the growth, development and yield of carrot

The effect of the BA-4 preparation during the pre-sowing treatment of carrot seeds on the growth, development and yield was tested in field conditions. The results of phenological observations show that in the experiments where carrot seeds have been soaked in the solutions of the 0.001% and 0.0001% concentrations of the BA-4 preparation, sprouted 3 and 6 days earlier, compared to the control. When treating seeds with the Extrasol standard, shoots have appeared 1 day earlier, compared to the control experiment. The phase of 2-4 and 6-8 true leaves when treated with the preparation in the concentration of 0.001% has occurred 3 days earlier; when treated in the concentration of 0.0001% - 6 days earlier (Table 3).

Table 3
Intensity of the emergence of seedlings and the development phases of carrots under the effect of the treatment with BA-4 in the field conditions.

Experiment variants		Seedling		2-4 leaf phase	6-8 leaf phase
	Primary		Massive
Control without the treatment	07.06		12.06	22.06	04.07
BA-4 0.001%	05.06		09.06	19.06	01.07
BA-4 0.0001%	03.06		06.06	16.06	28.06
HAU 0.06% (standard)	06.06		11.06	21.06	03.07

The pre-sowing seed treatment with the optimal concentrations increases the density of carrot plants. The data presented in Table 4 indicate that seed treatment with BA-4 in the concentration of 0.001% increases the density of plants by 14.3%, and in the concentration of 0.0001% - by 21.4%. Soaking in the HAU ​​solution (0.06%) increases the density of plants by 7.1%.

Table 4
The effect of BA-4 on the density of carrot plants in the field conditions.

Experiment variants Number of plants per 1 m2 Readings in %
Control without the treatment	70.0 ± 0.01	100.0 ± 0.01
BA-4 0.001%	80.0 ± 0.02	114.3 ± 0.2
BA-4 0.0001%	85.0 ± 0.01	121.4 ± 0.2
HAU 0.06% (standard)	75.0 ± 0.01	107.1 ± 0.02

It follows that the pre-sowing treatment of carrot seeds with BA-4 in the optimal concentration increases the density of standing, i.e. the field germination of carrot plants. The treatment of carrot seeds with the preparation in the optimal concentration has a significant effect on the growth and development of carrot plants: from the data presented in Table 5 it follows that the height of the plants grown from seeds treated with the preparation on the day of recording when using BA-4 has been higher, compared to the control on the 30^th, 45^th and 60^th day by 1.7, 3.2 and 1.4 cm in the concentration of 0.001%; and in the concentration of 0.0001% - by 2.2, 5.0 and 2.9 cm, respectively. The use of the standard leads to an insignificant increase in the plant height. The number of leaves on one plant grown from the seeds, treated with BA-4 in the concentration of 0.001%, have increased, compared to the control on the 30^th, 45^th and 60^th day by 0.7, 1.6 and 0.9 pcs; in the concentration of 0.0001% - by 1.1, 2.4 and 2.0 pcs, respectively. When treating the seeds with the standard in the concentration of 0.06%, the increase in the number of leaves has made up 0.4, 1.1 and 1.9 pcs, compared to the control.

Table 5
The effect of BA-4 on the growth and development of carrot plants in the field conditions.

Experiment variants	Seedling
	30 days		45 days		60 days
	Plant height	Number of leaves	Plant height	Number of leaves	Plant height	Number of leaves
Control without the treatment	8.0 ± 0.01	5.1 ± 0.01	12.0 ± 0.02	6.2 ± 0.03	15.2 ± 0.02	7.1 ± 0.03
BA-4 0.001%	9.7 ± 0.02	5.8 ± 0.01	15.2 ± 0.02	7.8 ± .0.02	16.6 ± 0.03	8.0 ± 0.02
BA-4 0.0001%	10.2 ± 0.01	6.2 ± 0.01	17.0 ± 0.01	8.6 ± 0.02	18.1 ± 0.02	9.1 ± 0.02
HAU 0.06% (standard)	9.0 ± 0.02	5.5 ± 0.01	14.0 ± 0.02	7.3 ± 0.02	17.0 ± 0.02	8.0 ± 0.02

Thus, the plants grown from the seeds, treated with the optimal concentration of the preparation, have grown and developed significantly better, which, in turn, has a positive effect on the increase in the mass of carrot roots (Table 5).

Thus, the increase in the mass of the roots on the 30^th, 45^th and 60^th days of recording in the variant with the BA-4 preparation in the concentration of 0.001%, has been 11.2 ± 0.01, 18.2 ± 0.02 and 32.0 ± 0.02 grams, and in the concentration of 0.0001% - 13.6 ± 0.02, 20.0 ± 0.02 and 40.0 ± 0.03 grams. When using the HAU standard (0.06%), the increase in mass has been 10.5 ± 0.01, 17.3 ± 0.02, 30.1 ± 0.02 grams, in the control variant - 9.0 ± 0.01, 16.0 ± 0.02 and 28.0 ± 0.02 grams (Table 6).

Table 6
The dynamics of the growth of carrot root crops.

Weight of carrot fruits, g
Experiment variants	30 days	45 days	60 days
Control without the treatment	9.0 ± 0.01	16.0 ± 0.02	28.0 ± 0.02
BA-4 0.001%	11.2 ± 0.01	18.2 ± 0.02	32.0 ± 0.02
BA-4 0.0001%	13.6 ± 0.02	20.0 ± 0.02	40.0 ± 0.03
HAU 0.06% (standard)	10.5 ± 0.01	17.3 ± 0.02	30.1 ± 0.02

The data on the carrot root yield, presented in Table 7, indicate that the pre-sowing treatment of carrot seeds with BA-4 in the concentration of 0.001% increases the yield by 3.5 ± 0.01 t/ha or 15.9 ± 0.02%, compared to the control; and in the concentration of 0.0001% - by 5.0 ± 0.02 t/ha or 22.7 ± 0.03%. The treatment with the 0.06% solution of the GAU standard has led to an increase in yield by 1.2 ± 0.02 t/ha or 5.5 ± 0.01%, compared to the control.

Table 7
The effect of the preparation on the yield of carrots of the “Alau” variety.

Experiment variants	Carrot yield, t/ha	Gain to the control
		t/ha	%
Control, without the treatment	22.0 ± 0.03	-	-
BA-4 0.001%	25.5 ± 0.01	3.5 ± 0.01	15.9 ± 0.02
BA-4 0.0001%	27.0 ± 0.02	5.0 ± 0.02	22.7 ± 0.03
HAU 0.06% (standard)	23.2 ± 0.01	1.2 ± 0.02	5.5 ± 0.01

• Note: P, % - 4.5 НСР _0,05 т/га — 0.8.

3.3. The effect of the BA-4 on the growth, development and yield of beetroot

Phenological observations of the growth and development of beetroot plants have shown that the seeds, treated in the 0.001 and 0.0001% solutions have emerged 2 and 5 days earlier than the control (Table 8). The 2-4 and 6-8 leaf phases have also preceded the control variant: at 0.001% - by 2 days, at 0.0001% - by 5 days.

Table 8
The effect of the new preparation on the emergence and development phases of beetroot plants.

		Seedling
Experiment variants	Primary		Massive	2-4	6-8
				leaf phase	leaf phase
Control, without treatment	26.05		02.06	12.06	24.06
BA-4 0.001%	23.05		31.05	10.06	22.06
BA-4 0.0001%	21.05		28.05	07.06	19.06
HAU 0.06% (standard)	25.05		01.06	11.06	23.06

The pre-sowing treatment of beetroot seeds increases the plant density. The data, presented in Table 9, indicate that the treatment of beet seeds with BA-4 in the concentration of 0.001% increases the plant density by 31.3%, and in the concentration of 0.0001% - by 37.5%. Soaking in the HAU solution (0.06%) increases the plant density by 13.8%.

Table 9
The effect of the new preparation on plant density of beetroot.

Experiment variants Number of fruit crops, 1 m2 Percentage compared to control
Control, without treatment	16.0 ± 0.03	100.0 ± 0.02
BA-4 0.001%	21.0 ± 0.02	131.3 ± 0.01
BA-4 0.0001%	22.0 ± 0.02	137.5 ± 0.01
HAU 0.06% (standard)	18.2 ± 0.02	113.8 ± 0.02

The significant of treating beetroot seeds with the preparation solutions has persisted until the end of the growing season. This is evidenced by the results of the biometric measurements. Thus, the analysis of the data presented in Table 10 shows that the plants grown from the seeds treated with BA-4 in the concentrations of 0.001 and 0.0001% have been taller than the control plants (on the day of recording) by 3.0, 2.8, 4.6 cm and 6.2, 5.5, 5.8 cm; for the standard - by 2.0, 4.0 and 2.0 cm, respectively. The number of leaves on the 60^th day after the emergence has been greater for BA-4 (0.001 and 0.0001%) by 1.7-5.1 pcs.; for the standard - by 2.7 pcs.

Table 10
Changes in the growth and development of the beetroot plants after the seed treatment with the new preparation BA-4.

Experiment variants	Seedling
	30 days		45 days		60 days
	Plant height	Number of leaves	Plant height	Number of leaves	Plant height	Number of leaves
Control, without treatment	8.0 ± 0.01	5.2 ± 0.01	11.0 ± 0.01	8.6 ± 0.01	16.0 ± 0.02	9.3 ± 0.02
BA-4 0.001%	11.0 ± 0.02	7.1 ± 0.02	13.8 ± 0.02	9.0 ± 0.02	20.6 ± 0.01	11.0 ± 0.02
BA-4 0.0001%	14.2 ± 0.01	9.2 ± 0.02	16.5 ± 0.02	13.0 ± 0.02	21.8 ± 0.02	14.4 ± 0.02
HAU 0.06% (standard)	10.0 ± 0.01	6.3 ± 0.02	15.0 ± 0.02	10.3 ± 0.01	18.0 ± 0.02	12.0 ± 0.03

The weight of the roots from the seeds treated with the BA-4 on the 30^th, 45^th and 60^th days of recording has been greater than the control for the concentrations of 0.001 and 0.0001% by 1.8, 2.1, 9.6 and by 4.8, 6.3, 13.0 grams, respectively (Table 11).

Table 11
Dynamics of the increase in the weight of the beetroot roots from the seeds, treated with the new preparation.

Experiment variants	Weight of cucumber fruits, g.
	30 days	45 days	60 days
Control, without treatment	12.2 ± 0.01	22.6 ± 0.02	35.6 ± 0.01
BA-4 0.001%	14.0 ± 0.02	24.7 ± 0.01	45.2 ± 0.01
BA-4 0.0001%	17.0 ± 0.02	28.9 ± 0.02	48.6 ± 0.01
HAU 0.06% (standard)	13.2 ± 0.02	26.1 ± 0.01	40.0 ± 0.02

The BA-4 preparation has activated the growth and development of the beetroot plants when treating the seeds, which in turn has led to an increase in the yield of the root crops. Thus, the maximum increase to the control was obtained when treating seeds with BA-4 at a concentration of 0.0001% and amounted to 6.3 ± 0,02 t/ha or 24.2% (Table 12).

Table 12
The effect of the new BA-4 preparation on the yield of the root crops of the “Kyzyl kuren” variety.

Experiment variants	Red beets yield (ton/ha)	Growing control
		ton/ha	%
Control, without treatment	26.0 ± 0.01	-	-
BA-4 0.001%	31.0 ± 0.02	5.0 ± 0.03	19.2 ± 0.03
BA-4 0.0001%	32.3 ± 0.01	6.3 ± 0.02	24.2 ± 0.009
HAU 0.06% (standard)	28.6 ± 0.02	1.2 ± 0.03	6.2 ± 0.02

• Note: P (%): 4.5. НСР 0.05 (ton ha^-1): 0.8.

3.4. The effect of BA-4 on the growth, development and yield of potatoes

Phenological observations have shown that in the variants where the tubers have been treated with BA-4 in the concentration of 0.0001% before planting, the shoots have emerged 6 days earlier than the control; when treated with Extrasol (10%), the shoots have emerged 1 day earlier than in the control variant (Table 13). Thus, the preparation, stimulating the germination of the potato tubers, has accelerated the emergence of shoots 4-6 days earlier.

Table 13
The effect of the new preparation on the germination, growth and development of the potato plants.

Experiment variants	Seedling		Bud formation phase	Flowering phase
	Primary	massive
Control without the treatment	04.06	12.06	04.07	09.07
BA-4 0.001%	31.05	08.06	30.06	05.07
BA-4 0.0001%	29.05	06.06	28.06	03.07
Extrasol 10% (standard)	03.06	11.06	03.07	08.07

The plants grown from the treated tubers have grown and developed better, and have been noted for having a larger mass of potato foliage. Thus, from Table 14 it is evident that the mass of tops in the variant where the tubers have been treated with BA-4 before planting, from the beginning of the growing season has exceeded the mass of tops in the control variant: under the effect of the preparation in the concentration of 0.0001%, the mass of tops has been 130 g more than in the control variant at the first count, and 135 g more at the second count; in the Extrasol standard (10%) – by 17 and 30 g. The acceleration of the growth of the mass of the above-ground part of plants has been observed until the end of the growing season.

Table 14
The effect of BA-4 on the growth and development of the above-ground part of the potato plants.

Experiment variants	Seedling
	Including			Including
	tops	stems	leaflets	tops	stems	leaflets
	on the 45 days after germination			on the 60 days after germination
Control without the treatment	250.0	95.0	155.0	320.0	120.0	200.0
BA-4 0.001%	361.0	111.0	250.0	412.0	131.0	281.0
BA-4 0.0001%	380.0	120.0	260.0	455.0	150.0	305.0
Extrasol 10% (standard)	26.0	106.0	161.0	350.0	127.0	223.0

The yield formation depends not only on the assimilation surface of the potato plants, but also on the formed number of the tubers. As can be seen from Table 15, the studied treatments has had a positive effect on the tuberization process. Thus, at the first determination date (on the 45^th day after the emergence), 6.1 ± 0.02 tubers per bush have been in the control variant, and 8.0 ± 0.05 tubers per bush have been in the variant with the BA-4 preparation in the concentration of 0.001%; in the concentration of 0.0001% - 9.1 ± 0.01 tubers, and 6.5 ± 0.01 tubers - in the variant with the standard. At the second determination date (on the 60^th day after the emergence), 7.0 ± 0.02 tubers per bush have been in the control, and 8.6 ± 0.02 tubers per bush have been in the variant with the BA-4 preparation in the concentration of 0.001%, and 11.5 ± 0.01 pieces of tubers in the concentration of 0.0001%, respectively; 8.3 ± 0.01 pieces of tubers - in the variant with the standard (Dzhiembaev et al., 2022).

Table 15
The effect of the new preparation on the potato tuber formation.

Experiment variants	The number of tubers per 1 bush, pcs.
	Total	More than 80 g	25-80 g	Less than 25 g	Total	More than 80 g	25-80 g	Less than 25 g
		on the 45th day after the germination				on the 60th day after the germination
Control without the treatment	6.1 ± 0.02	1.2 ± 0.02 3.8 ± 0.01		1.1 ± 0.01	7.0 ± 0.02	2.6 ± 0.01	2.2 ± 0.01 2.2 ± 0.01
BA-4 0.001%	8.0 ± 0.05	2.0 ± 0.05 5.0 ± 0.01		1.0 ± 0.05	8.6 ± 0.02	4.0 ± 0.02	3.1 ± 0.02 1.5 ± 0.01
BA-4 0.0001%	9.1 ± 0.01	3.0 ± 0.02 5.1 ± 0.01		0.9 ± 0.01	11.5 ± 0.01	5.0 ± 0.01	4.3 ± 0.01 2.2 ± 0.02
Extrasol 10% (standard)	6.5 ± 0.01	1.3 ± 0.01 4.0 ± 0.01		1.2 ± 0.01	8.3 ± 0.01	2.5 ± 0.02	3.0 ± 0.01 2.8 ± 0.01

The active growth and development of potatoes has had a positive effect on the process of tuberization, which ultimately has led to an increase in the potato yields (Table 16). The data in the Table show that the treatment of the tubers with BA-4 in the concentration of 0.001% increases the potato yield by 4.3 ± 0.01 t/ha or 18.9 ± 0.03%, compared with the control variant; and in the concentration of 0.0001% – by 7.3 ± 0.01 t/ha or 32.2 ± 0.02%. The treatment of the tubers with the Extrasol standard preparation (10.0%) increases the potato yield by 2.3 ± 0.02 t/ha or 10.1 ± 0.02%.

Table 16
The effect of the pre-treatment of the seeds with the new preparation on the yield of potatoes of the “Aksor” variety.

Experiment variants	Carrot yield, t/ha	Gain to the control
		t/ha	%
Control without the treatment	22.7 ± 0.01	-	-
BA-4 0.001%	27.0 ± 0.01	4.3 ± 0.01	18.9 ± 0.03
BA-4 0.0001%	30.0 ± 0.01	7.3 ± 0.01	32.2 ± 0.02
Extrasol 10.0% (srtandard)	25.0 ± 0.01	2.3 ± 0.02	10.1 ± 0.02

• Note: P,% - 4.1; НСР_0.05 т/га — 0.9.

4. Discussion

The study has found that the new BA-4 preparation has the pronounced plant growth stimulating properties. The pre-sowing treatment of the seed material in low concentrations (0.001 and 0.0001%) has a positive effect on the germination energy, seed germination, plant growth and development, as well as their final yield. The results of the experiments demonstrate that BA-4 in the concentration of 0.0001% has the greatest effect on the germination energy and germination of carrot and seeds, increasing the indicators by 19-24% and 11-17%, respectively. Compared to the control, the treatment with BA-4 has also increased the number of the awakened buds in potato tubers by 60%, which is a significant result. When compared with the reference preparation GAU (heteroauxin) and Extrasol, BA-4 has demonstrated higher efficiency in stimulating the growth and increasing the yield. Thus, the yield of carrot has increased by 22.7%, that of by 24.2%, and that of potato by 32.2%. At the same time, HAU has provided an increase in the carrot yield by only 5.5%, and Extrasol has increased the potato yield by 10.1%.

The growth-stimulating effect of BA-4 may be associated with the activation of the metabolic processes in plants, improved absorption of nutrients, and increased stress resistance. These results are consistent with the previous studies in the field of plant growth regulators (Shah et al., 2021; Fahad et al., 2016), where similar compounds have shown a stimulating effect on the morphophysiological development of plants.

Based on the results obtained, it is possible to recommend the use of BA-4 in agriculture to increase the productivity of vegetable crops. Given its effectiveness even in low concentrations, the preparation may become a promising alternative to the traditional growth stimulants. Besides, its use reduces the need for agrochemicals, which contributes to the environmental sustainability of the agricultural production. Despite the positive results, a further study of the possible effect of BA-4 on the product quality, accumulation of the biologically active substances in plants, and its effect on soil microflora is required. The future studies may include a molecular analysis of the mechanisms of the BA-4 action, as well as its testing on other crops and under various agroclimatic conditions.

The results obtained confirm that BA-4 is an effective plant growth stimulant. The use of this compound can significantly increase crop yields and accelerate the growth of the agricultural crops. Plant growth regulators are chemical compounds, which act as mediators in the management of various phenological, physiological and metabolic processes in plants. They are synthesized by cells and regulate their functions by affecting the receptor proteins and activating the signaling pathways within the cells. Plant growth regulators help improve the biological functions of plants by ensuring water availability, optimal nutrient content and enzyme activity (Rademacher, 2015; Shah et al., 2021; Fahad et al., 2016). The pre-sowing treatment of the seed material in low concentrations (0.001 and 0.0001%) of N-(1-ethynylcyclohexyl)amide O,O-diethylphosphoric acid increases the germination energy of carrot seeds by 19.0 and 24.0%. The seed germination increases by 7.0 and 19.0% in the BA-4 concentrations of 0.001 and 0.0001%, compared to the control. The results of the laboratory studies have shown that the treatment of beetroot seeds in the BA-4 solution in the concentration of 0.001% increases the seed germination energy by 5.0%, germination - by 10.0%; in the concentration of 0.0001% - by 11.0 and 17.0%, respectively. The HAU standard (0.06%) increases the germination energy by 9.0% and germination by 10.0%. The results of the laboratory studies have shown that the use of BA-4 when treating the tubers with BA-4 in the concentration of 0.001% increases the number of the awakened buds by 43.0% compared to the control. Treating the tubers with BA-4 in the concentration of 0.0001% increases the number of the awakened buds by 60.0% compared to the control. When using BA-4 in the concentration of 0.001%, the carrot seed yield has increased by 3.5 t/ha or 15.9%, and in the concentration of 0.0001% - by 5.0 t/ha or 22.7%. The treatment with the 0.06% solution of the HAU standard has led to an increase in the yield by 1.2 t/ha or 5.5%, compared to the control. When treating beetroot seeds with BA-4 in the concentration of 0.0001%, it has been 6.3 t/ha or 24.2%. The potato yield has increased by 4.3 t/ha or 18.9%, compared to the control after using BA-4 in the concentration of 0.001%; ​​and in the concentration of 0.0001% - by 7.3 t/ha or 32.2%. Treating the tubers with the standard preparation Extrasol (10.0%) increases the potato yield by 2.3 t/ha (10.1%).

Result of laboratory and field studies N-(1-ethynylcyclohexyl)amide of O,O-diethylphosphoric acid (BA-4) was found to have pronounced plant growth-stimulating properties. It has been established that the optimal concentration for BA-4 is 0.0001%. When treating the carrot, and potato tubers with the specified preparation in the optimal doses, plant shoots have appeared 2-4 days earlier. The density of plant standing (the field germination) when treating the carrot seeds with BA-4 in the concentration of 0.0001% has increased by 21.4%. The pre-sowing treatment of the seeds with BA-4 in the concentration of 0.0001% has increased the density of plant standing by 37.5%. The studied preparation has a positive effect on the process of the potato tuber formation. At the first determination date (on the 45^th day after the emergence) 9.1 tubers per 1 bush have been in the variant with the BA-4 preparation in the concentration of 0.0001%; 11.5 tubers have been at the second determination date (on the 60^th day after emergence) in the variant with a similar concentration. The field tests have shown that the plants grown from the seeds and tubers, pre-soaked in the solutions of the tested synthetic preparation, conventionally called BA-4, have grown and developed better, which ultimately has led to an increase in the yield of the vegetable crops. Thus, the use of the BA-4 preparation in the optimal concentration of 0.0001% has led to an increase in the yield of carrots by 5.0 t/ha (22.7%), beetroots by 6.3 t/ha (24.2%) and potatoes by 7.3 t/ ha (32.2%).

Acknowledgements

This research has been funded by the Science Committee of the Ministry of Science and Higher Education of the Republic of Kazakhstan АР No. 19678514 “Synthesis, structure and biological properties of new effective domestic preparations as plant growth and development regulators”.

Data Availability Statement

All data generated or analyzed during this study are included in this published article.

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Edited by

• Editor:
  Takako Matsumura Tundisi

Publication Dates

• Publication in this collection
  29 Sept 2025
• Date of issue
  2025

History

• Received
  02 Apr 2025
• Accepted
  12 Aug 2025