RU2455297C2 - N-[4-(2-furyl)-2-butyl]-n-2,4-dichlorophenylurea, exhibiting multifunctional plant morphogenesis regulator and crop immunomodulator properties - Google Patents

Abstract

FIELD: chemistry.

SUBSTANCE: present invention relates to an agent which is a chemical compound N-[4-(2-furyl)-2-butyl]-N-2,4-dichlorophenylurea of formula

which exhibits multifunctional growth-regulating and immunomodulating activity.

EFFECT: obtaining a highly effective, low-toxicity, environmentally safe agent having complex positive action on plant morphogenesis and immunomodulation with the aim of increasing productivity of crops.

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Description

The invention relates to the field of agriculture and to the chemistry of biologically active substances, namely to a new chemical compound of the formula

possessing high growth-regulating and immunomodulating activity.

The inventive object of formula I by chemical structure is disubstituted asymmetric urea containing heterocyclic (furylalkyl) and aromatic (dichlorophenyl) substituents. Analogues in the structure of the claimed object I are substituted urea, which currently represent the most numerous class of pesticidal agents. (List of pesticides and agrochemicals approved for use on the territory of the Russian Federation // Appendix to the journal “Protection and Quarantine of Plants." - 2000. - N3. - P.303), including those containing heterocyclic substituents of various series. However, urea, containing the furan cycle are still poorly studied, possibly due to the lack of available methods for their synthesis until recently, while natural phytohormones with cytokinin activity, i.e., intensifying cell division, increase which reduce the resistance of plants to diseases are N, N'-diphenylurea (1) and 6-furfuriladenin (2), or kinetin:

Thus, the combination of two biologically active fragments (furan and urea) in a chemical compound molecule can be very promising when modeling the structure of a highly effective synthetic plant growth and development regulator.

A synthetic analogue of the claimed biological activity object is 2- (5R-Aminomethylfuryl-2) -1,3-dioxolanes (3), exhibiting growth-regulating and anti-stress activity (RF patent No. 2288230, IPC C07D 407/04); and its derivatives (4) as growth regulators of fruits and vegetables (French application No. 2666963, IPC A01N 43/02, 43/08); salts of 1-phenyl-3- (1,2,4-triazol-4-yl) urea (5) with cytokinin activity (RF patent No. 1732651, IPC C07D 249/08):

,

,

R ¹ = H, alkyl;

R ² = H, Me ⁺ , N (CH ₃ ) ₂

alkyl, cycloalkyl.

A common structural element with the proposed technical solution is the presence of a furan cycle (compounds 3, 4), however, the latter do not belong to the class of heterocyclic derivatives of urea. Compound 5 contains an isourea fragment, however, the heterocyclic part of the molecule is represented by a triazole rather than a furan ring. Compounds 3-5 do not have immunomodulatory activity.

Among the substituted ureas that have pesticidal activity and are approved for use on the territory of the Russian Federation, the analogue of the claimed technical solution is the drug monuron - N, N-dimethyl-N'-4-chlorophenylurea (6) (Pesticides: Reference book / V.I. Martynenko, V.K.Promonenkov et al. M .: Agropromizdat, 1992, - S.368, 205, 216).

Compound 6 does not have a growth-regulating effect, being a herbicide with a consumption rate of 4 kg / ha. The closest in structure and biological effect to the claimed object is the previously synthesized by us di-N, N '- [4- (2-furyl) -2-butyl] urea (II), which exhibits growth-regulating and immunomodulating activity (RF patent No. 2349590, IPC C07 / D 307/52, 407/12, A01N 49/08).

The claimed compound I differs from the known bioregulator II by the presence of a 2,4-dichlorophenyl substituent in the urea fragment, while prototype II is a disubstituted furylbutyl carbamide. The existing differences in the structure of compounds I and II lead to the appearance of the claimed compound I morphogenetic and immunomodulatory activity exceeding that of prototype II.

The technical objectives of this invention are:

- the search for new biologically active compounds of the aryl (heteryl) class of substituted urea exhibiting growth-regulating activity against various crops at a low consumption rate;

- the search for effective immunomodulators that increase the resistance of crops to a wide range of phytopathogens of fungal and viral etiology in connection with the problem of multiresistance of microorganisms to modern pesticidal agents;

- expanding the range of highly effective low-toxic, environmentally friendly products with a comprehensive positive effect on plant morphogenesis and immunomodulation in order to increase agricultural productivity.

The technical result is to increase the total, early and commercial productivity of vegetable, grain and forage crops, as well as a significant reduction in the degree of development and prevalence of the main fungal and viral diseases caused by phytopathogens.

To solve these problems, a new chemical compound of the class of N-furylalkyl-N'-arylcarbamides was obtained, namely: N- [4- (2-furyl-2-butyl)] - N'-2,4-dichlorophenylurea of the formula I

Positive plant morphogenesis, manifested as a result of pre-sowing treatment of seeds of agricultural crops (vegetables, grains, fodder) with an aqueous solution of drug I at a concentration of 3.2 · 10 ^-4 -3.2 · 10 ^-5 mol / l (consumption rate 50 mg / ha ) is multifunctional, causing positive changes in the structure of both the root system and the aerial parts of plants (Tables 1-6), phenological signs (early germination, acceleration of the passage of phases of organogenesis (Tables 5, 6), improvement of qualitative (Tables 2, 3, 4) and an increase in quantitative indicators yields (Tables 3, 4) and seed productivity (Tables 7), including an increase in protein, cereal gluten (Tables 10, 11), weight of fruits and tubers (Tables 2-4), total and commodity yield.

A comparative analysis of the biological effects of the claimed object I and prototype (reference) II shows that at the same concentration of drugs, the activity of compound I exceeds that of prototype II, as well as the widely used standard bioregulators. In addition, the claimed drug has a biostimulating effect on a wider range of vegetable crops, including, in contrast to drug II, root crops (potatoes, etc., tables 4, 7).

The immunomodulatory activity of the claimed drug I as well as prototype II, is versatile, covering a wide range of pathogens and crops. However, the degree of influence of the drug I on the processes of cellular metabolism and the formation of plant immunity is deeper, as a result of which the claimed object is superior to prototype II in terms of the effectiveness of bioprotective and immunomodulating effects (Tables 7, 8, 9, 11).

A compound of formula I having growth-regulating and immunomodulating activity is not described in the literature. The inventive object is a synthetically accessible compound and can be obtained by a known preparatively convenient method by the interaction of a primary amine with an arylisocyanate [TP Vishnyakova, IA Golubeva, EV Glebova. Substituted urea, methods of synthesis and scope // Uspekhi khimii. - 1985. - T.54. issue 3, - S.429-448].

The invention is illustrated by examples of specific performance.

Example 1. Synthesis of N- [4- (2-furyl-2-butyl) -N'-2,4-dichlorophenylurea (I)

To a solution of 13.9 g (0.1 mol) of 4- (2-furyl) -2-aminobutane obtained by the method [a.w. USSR No. 1204617, IPC C07D 207/08. A method of obtaining derivatives of 3- (2'-pyrrolidyl) propanols. / I.N. Klochkova, M.V. Noritsina, O.Yu.Rasstegaev, O.A. Anisimova. Application 33709963, prior. from 01/09/84. Publ. BI - 1986. - N2. - C.20] in 120 ml of absolute dioxane, 18.8 g (0.1 mol) of 2,4-dichlorophenyl isocyanate are added dropwise with constant stirring. The reaction mixture is maintained at a temperature of 60-80 ° C for 1.5-2 hours. Monitoring the progress of the reaction is carried out by thin layer chromatography. At the end of the reaction, the solvent was distilled off under reduced pressure, and the residue was recrystallized from ethanol. Get I in the form of colorless crystals, t _PL 151-152 ° C. Yield 31.1 g (95%).

Found,%: C55.10; H 4.92; N, 8.50: Cl, 21.48. C7H3ONCl2. Calculated,%: C 55.04; H 4.89; N, 8.56; Cl 21.48.

The following characteristic bands (ν, cm -1) are present in the IR spectrum of compound I: 3310 (ν NH); 3000, 3080 (ν = CH); 2960, 2880, 2840 (ν CH2, CH3); 1620 (ν СО); 1600 (ν C = C); 1450, 1380 (δ CH2, CH3); 860, 820, 730 (δ = CH). The electronic spectrum of compound I contains two absorption bands with maxima of 247 nm (log ε 4.40), 290 nm (log ε 2.26).

Example 2. Field trials of growth-regulating action of N- [4- (2-furyl-2-butyl)] - N'-2,4-dichlorophenylurea (DCBFM) I

The experiments were conducted on spring wheat of the Albidum 188 variety, Kustovoy cucumbers, Nevsky potatoes, Novichok tomatoes, and Zaikevich alfalfa.

Field experiments on wheat were laid in the Volgograd region from 2005 to 2007, on cucumbers - in the conditions of the Samara region from 2004 to 2006, on tomatoes - in the Engels district of the Saratov region from 2005 to 2007, on potatoes - in the conditions of the Arkadak district of the Saratov region in 2006-2008, on alfalfa - in the conditions of the Ershov experimental station in the Saratov region in 2006-2008.

Bookmarking experiments, harvesting and recording yields were carried out in accordance with Gosstandart [Methodology of state variety testing of crops. M. - 1985. - issue 2 - S.286].

Before sowing, seeds and tubers of plants were treated by soaking in a solution of DCBFM with an active substance concentration of 3 · 10 ^-4 % or 3 · 10 ^-3 %, which corresponds to 3.2 · 10 ^-5 and 3.2 · 10 ^-4 molar concentrations [ Belik V.F., Krotova R.A. Seed quality, methods for their pre-sowing preparation // Sat. open-field vegetable growing. - M .: Kolos - 1984. P.108].

Water served as a control in the experiments, an aqueous solution of succinic acid with a concentration of 2 · 10 ^-3 % (in experiments with alfalfa) and a solution of a multipurpose stimulator of protective reactions, plant growth and development — immunocytophyte of the same concentration were taken as a standard [Kulnev A.I. ., Sokolova E.A. Multipurpose stimulants of protective reactions, growth and development of plants. Pushchino: ONTI PNC RAS. - 1997. - 100 p.) In experiments with vegetables and crops.

Tomatoes were planted in seedlings in open ground 45 days after sowing seeds.

Wheat, alfalfa, cucumbers and potatoes were sown and planted directly into the soil with soaked and then dried seeds and tubers.

As a reference standard (prototype), an aqueous solution of N, N'-butylfurylurea (II) was used [Klochkova I.N., Suslova T.A. et al. Pat. RF №2349590, IPC C07D 307/52, C07D 407/12] at a concentration of 3 · 10 ^-3 -3 · 10 ^-4 %.

The repetition of the experiments is 4-fold. The sizes of accounting plots for all crops are 25 m ² , the protection zone is 1.5 m ² .

For accounting, 10 plants were taken from each repetition.

The experiments were laid on chernozem soils.

Spring wheat was placed on a layer of perennial grasses, which, after removing the last mowing, was treated with disk implements in two directions to a depth of 8-10 cm, after which fertilizers were applied. In spring, when the soil ripened, it was buried.

Soil preparation for vegetables and alfalfa included peeling, autumn plowing to a depth of 25-30 cm, spring harrowing, double cultivation. Potatoes were planted using the comb method.

Phosphate-potassium fertilizers were applied to wheat, which were applied for chill, part of the phosphorus was applied during sowing. Nitrogen was introduced in the form of ammonium nitrate fractionally: 50% of the dose - before the start of the growing season, and the rest in two dressings.

Before planting tomato seedlings, fertilizers were applied (superphosphate at a rate of 4 kg / ha, potassium chloride at a rate of 2 kg / ha), and ammonia nitrate was added during cultivation (at a rate of 1.5 kg / ha).

In the same way, fertilizers were applied under the cucumbers.

Ammonium nitrate, double superphosphate, potassium chloride and ammonium phosphate (2: 3: 3: 3) were used as fertilizers on potatoes.

Winter wheat was chosen as the predecessor of alfalfa. In autumn, full mineral fertilizer N60P80K80 was added under plowing. During the growing season, after each mowing, top dressing was applied (total N45P90K90).

During the vegetation period of wheat, vegetative irrigation was carried out: one at the end of tillering, the second into trumping, the third at heading. The irrigation rate was 1800-3400 m ² / ha.

6-10 seasonal irrigation was carried out on tomatoes and cucumbers, 4 irrigation on potatoes.

Alfalfa was grown under irrigation conditions.

The test results are presented in table.1-7.

From tables 1, 2, 3, 4 it can be seen that pre-sowing treatment of DCBFM seed material in the form of solutions with a concentration of 3.2 · 10 ^-5 and 3.2 · 10 ^-4 mol / l (M) contributed to an increase in yield in various crops by compared with the control of 12-100%.

The processing of Novichok tomatoes with a solution of DHFBM at a concentration of 3.2 · 10 ^-5 M, when the plant productivity increased by 2 times compared with the control, was especially effective. Under the influence of the treatment, the mass of the 1st fruit practically did not change, but their number from the 1st plant doubled, which gave a high total yield from the plot.

The use of DHBFM for growing cucumbers and potatoes also had a significant positive effect on crop productivity. The increase in the yield of cucumbers and potatoes in the variant with DCBFM was 40 and 50%, respectively, the number of fruits from the 1st plant and the weight of one fruit increased significantly.

The use of DCBFM in the cultivation of alfalfa also led to an increase in the yield of green mass, an average of 12% in relation to the control.

An important indicator of vegetable crops is their ability to produce early marketable products. The treatment of seeds of tomatoes and cucumbers with DHBPM positively affected this symptom. Under the influence of DCBFM treatment, field germination increased in cucumbers and tomatoes and fruit ripening occurred 2-8 days earlier than in the control (Tables 5, 6).

The use of DHBFM had a positive effect on the seed productivity of tomatoes. The seed yield compared to the control increased by 48%, and in relation to the standard and the standard by 45% and 35%, respectively (Table 7).

Example 3. The study of DCBFM as an inducer of resistance to fungal infections in various crops.

In the field, the degree of development and prevalence of the main fungal diseases was taken into account for all cultures: powdery mildew on cucumbers; on tomatoes - apical rot and late blight; on potato - late blight; on alfalfa - mycoplasmosis ("witch's broom"), on wheat - brown rust [Phytosanitary examination of crops. / M.: FGNU, Rosinformagroteh, Ministry of Agriculture of the Russian Federation. - 2002. - 134.p.].

Statistical processing of the results was carried out according to the method [Armor B.A. The technique of experimental work. M .: Kolos. - 1985. - 111.c.].

The results are illustrated in table 8-12. From table 8 it is seen that pre-sowing seed treatment with solutions of DHBPM reduced the development and prevalence of the main fungal infections characteristic of these crops.

So, under the influence of processing, the degree of powdery mildew in cucumbers significantly decreased - by 12.5% and 22.7%, respectively. The variant with a concentration of DCBFM 3.2 · 10 ^-5 M was close in this indicator to the standard.

A significant effect from the treatment of DHBFM was obtained on tomatoes. Under the influence of the drug, the prevalence of vertebral decay significantly decreased - 2 times compared with the control.

Plants treated with DHBPM in both concentrations were not affected by late blight.

The drug DCBFM reduced the development of late blight in potatoes. The degree of disease development in the treated plants was twice lower than in the control samples and 3 times lower relative to the standard.

The effect of treating alfalfa seeds with DHBPM was slightly lower than in vegetables. However, the prevalence of plants by mycoplasmosis decreased significantly enough.

Under the influence of treatment with DHBFM, the prevalence of wheat by brown rust has significantly decreased. The effect of the treatment was observed at all stages of plant development (table 9).

The reduction in the degree of development and prevalence of major plant diseases under the influence of treatment with solutions of DHBPM can be attributed to environmentally friendly, resource-saving technologies for cultivating crops.

The use of small doses of the drug is cost-effective, does not harm the environment, eliminates the use of pesticides, allows you to get environmentally friendly products.

Example 4. The effect of DHBPM on the biochemical processes of cellular metabolism of wheat Albidum 188.

In the leaves of Albidum 188 wheat plants obtained from treated seeds, the dynamics of dry matter accumulation was determined [Guidelines for the determination of chemicals for assessing the quality of fodder plants / All-Union Research Institute of Plant Production named after N.I. Vavilova. Leningrad. 1976 - S. 93]. As can be seen from table 10, in the variant with the preparation DHBPM at a concentration of 3.2 · 10 ^-4 M more dry matter accumulated at all stages of plant development than in the control and standard, which indicates the intensification of photosynthetic processes in the leaves under the action of the preparation.

A number of chemical indicators were also determined in wheat grain — protein, gluten and gluten content [Methodological recommendations for assessing grain quality / M .: VASKHNIL. Scientific Grain Quality Advice. 1977 - 172 p.].

The effect of DHBPM on these indicators is presented in table 11. Under the influence of processing, the protein content increased by 18% compared to the control and exceeded this indicator in relation to the standard and standard by 11% and 8.5%, respectively. The amount of gluten in grain is directly dependent on the total amount of protein, which is confirmed by our data. The quality of gluten in all variants of the experiment in terms of the index of IDK was “satisfactory weak” and there was no significant effect of the preparation DHBPM on this indicator.

Example 5. Laboratory studies of the growth-regulating action of DHBPM to assess the activity of the peroxidase enzyme.

In laboratory conditions, seeds and tubers were germinated, treated by soaking in appropriate solutions. The seeds of wheat, cucumber, tomatoes and alfalfa were germinated in wet rolls of filter paper in a thermostat at 24-25 ° C until sprouts 15-20 mm long appeared [Large practical workshop on plant physiology / Govrilenko V.F., Ladygina M.E., Handobina L.M. / M .: Higher. school - 1975. - 391 p.].

Treated potato tubers were placed in a wet peat sand substrate prepared in a 1: 1 ratio and germinated in an incubator at 24-25 ° C.

The resulting sprouts were separated from seeds and tubers and triturated with cold 0.2 M acetate buffer (pH = 4.7) in a ratio of 1:10. The suspension was infused in the refrigerator for 12 hours, then centrifuged at 1200 g. The activity of the peroxidase enzyme was determined in the supernatant by the method [Suslova TA, Khorosheva TM To the question of biochemical aspects of alfalfa resistance to mycoplasmosis // Plant Protection: Sat. scientific works. Saratov. Ed. SHI. - 1993. - S.111-119].

The effect of DCBFM was determined in relation to water, standard and standard (prototype).

The results of the studies indicate that the treatment of seeds with DCBFM solutions, especially at a concentration of 3.2 · 10 ^-4 M, significantly increased the activity of the peroxidase enzyme in seedlings (Table 12).

Oxidases, as you know, are the basis of enzyme systems that catalyze redox processes in the cell. It is likely that the drug of formula I is able to interact with peroxidase as a low molecular weight bioregulator to form its own effective enzymatic system in which the enzymatic activity of peroxidase exceeds that with the participation of natural flavin coenzymes. The consequence of this is the intensification of metabolic processes, which leads to positive changes in the morphogenetic and immune properties of plant cells.

Thus, according to the results of many years of laboratory and field studies of the preparation DHBPM (I), we can conclude that it has high biological activity.

The drug has multifunctional regulatory properties, which is probably due to the intensification of cellular metabolism processes under the influence of the drug. The consequence of this is a positive morphogenesis of plant cells at different stages of plant development, and in practical terms - an increase in the total and marketable productivity of vegetables, grains and fodder crops, and, consequently, an increase in their profitability.

Data on the prevalence and degree of inhibition of the development of major fungal infections in plants also indicate the protective properties of DCBFM in relation to a wide range of plant pathogens of fungal etiology.

The detected morphogenetic and immunomodulating activity of the preparation of the formula I exceeds that of the known biostimulants (standards) and analogue in structure (prototype, standard) II.

The proposed compound of formula I is used only for pre-sowing seed treatment in low concentration (3.2 · 10 ^-4 -3.2 · 10 ^-5 mol / l) of aqueous solutions at a rate of 50 mg / ha. The compound is stable in aqueous solutions, colorless, odorless, low toxic (LD50 is 1450 mg / kg animal weight (outbred white mice)). The new drug expands the arsenal of highly effective growth regulators that increase disease resistance and exhibit morphogenetic activity at the same time.

The discovered positive effect of the preparation of formula I on the intensification of growth processes, qualitative and quantitative indicators of yield, seed productivity and increased resistance to a number of diseases of the fungal and viral etiology of the most important grain, vegetable and fodder crops of open and protected soil suggests the possibility of using the compound of formula I in agricultural production as a growth regulator and immunomodulator.

Table 3 The effect of treatment with DHBFM on the productivity of cucumber cultivar Kustova (average for 2005-2007) Experience Options The number of fruits from the 1st plant, pcs. The mass of fruits from the 1st plant, kg Mass of the 1st fetus, g Productivity kg / m ² % increase The control 32 2.5 81 9,4 - DHBPM (I), 3.2 · 10 ^-5 M 36 3.0 91 13,2 40 DHBFM (I), 3.2 · 10 ^-4 M 38 3.2 90 14.8 57 Standard (prototype) (II), 10 ^-3 % 32 2.6 92 13.6 42 Standard (prototype) (II), 10 ^-4 % 34 2,8 94 13.8 53 Standard 42 4.0 102 15.4 64 NDS 0.5 2.0 0.5 7.5 3.4 -

Table 4 The effect of treatment with DHBFM on the productivity of Nevsky potato (average for 2004-2006) Experience Options The number of tubers from the 1st plant, pcs. The mass of tubers from the 1st plant, kg The mass of the 1st tuber, kg Productivity c / ha % increase The control 10 1,5 0.13 70 - DHBFM (I), 3.2 · 10 ^-4 M eighteen 2.2 0.16 105 fifty Standard (prototype) (II), 10 ^-4 % 13 1,5 0.10 94 34 Standard 12 1.9 0.12 92 31 NDS 0.5 1.8 0.3 0.02 8.5 -

Table 8 The effect of treatment with DCBFM on resistance to fungal infections in different crops (average over the years of the study) Culture, typical diseases Cucumbers Tomatoes Potatoes Alfalfa The degree of damage by powdery mildew,% * ** The degree of late blight,% Mycoplasmosis affection,% Experience Options The control 43.5 4.8 12.5 25 42.3 DHBPM (I), 3.2 · 10 ^-5 M 20.8 2,8 0 10 33.5 DHBFM (I), 3.2 · 10 ^-4 M 31,0 2.1 0 13 38.4 Standard (prototype) (II), 10 ^-4 % 44.0 4.4 10.5 36.0 41.5 Standard (prototype) (II), 10 ^-3 % 49.0 4.6 15.0 32,0 39.0 Standard 15,5 1.9 0 24 42.3 NDS 0.5 5,0 0.1 - 4.2 1.8 * - the prevalence of vertex rot,% ** - prevalence of late blight,%

Table 9 The effect of treatment with DHBFM on the resistance of brown varieties of Albidum 188 to brown rust (average for 2005-2007) Experience Options Prevalence,% Tillering phase Earing phase The control 10.0 12.0 DHBFM (I), 3.2 · 10 ^-4 M 5.9 7.0 Standard (prototype) (II), 10 ^-5 % 6.4 8.9 Standard 7.0 8.1 NDS 0.5 2.7 1.8

Table 10 The effect of treatment with DCBFM on the dynamics of dry matter synthesis in wheat leaves Albidum 188 (average for 2005-2007) Experience Options The amount of dry matter in the leaves,% Tillering Pounding Heading Milk-wax ripeness The control 4.1 7.5 9.9 10,4 DHBFM (I), 3.2 · 10 ^-4 M 5,6 10.5 10.6 10.8 Standard (prototype) (II), 10 ^-5 % 5,0 8.4 8.8 9.3 Standard 4,5 9.2 10.0 10.6 NDS 0.5 0.3 0.2 0.5 0.2

Table 11 The effect of treatment with DCBFM on the protein and gluten content in wheat grain Albidum 188 (average for 2005-2007) Experience Options The protein content,% Gluten content,% Gluten quality, units Idk The control 10.5 24.6 87.5 DHBFM (I), 3.2 · 10 ^-4 M 12,4 28.6 83.0 Standard (prototype) (II), 10 ^-5 % 11.5 28.3 82.0 Standard 11,2 28,2 85.0 NDS 0.5 0.4 2.0 2.5

Table 12 The effect of the preparation DHBPM on the activity of the enzyme peroxidase (unit / 100 g of crude substance) in plant seedlings (average over the years of the study) Culture Lucerne, Zaikevich variety Cucumbers, Kustovoi variety Tomatoes, grade Novichok Potatoes, grade Nevsky Wheat, grade Albidum Experience Options The control 500 80 fifty 3700 185 DHBPM (I), 3.2 · 10 ^-5 M 800 89 120 6000 660 DHBFM (I), 3.2 · 10 ^-4 M 900 105 200 6900 720 Standard (prototype) (II), 10 ^-4 % 700 86 110 4000 219 Standard (prototype) (II), 10 ^-3 % 800 98 140 4600 244 Standard 625 92 120 5000 665 NDS 0.5 9.1 2,3 7.4 12.6 9,4

Claims (1)

An agent having the property of a plant morphogenesis regulator and an immunomodulator of agricultural structures, which is an N- [4- (2-furyl) -2-butyl] -N'-2,4-dichlorophenylurea compound of the formula