AU2019101540A4

AU2019101540A4 - Use of Schiff Base Derivative from Dehydroabietylamine and (Substituted) Benzaldehyde

Info

Publication number: AU2019101540A4
Application number: AU2019101540A
Authority: AU
Inventors: Xiaoping Rao; Shibin SHANG; Zhanqian Song; Ji Xu; Zhaolan ZHAI
Original assignee: Institute of Chemical Industry of Forest Products of CAF
Current assignee: Institute of Chemical Industry of Forest Products of CAF
Priority date: 2019-09-30
Filing date: 2019-12-09
Publication date: 2020-01-23
Anticipated expiration: 2027-12-09
Also published as: CN110625720B; CN110625720A

Abstract

Abstract The present invention discloses the use of a Schiff base derivative from dehydroabietylamine and (substituted) benzaldehyde for wood preservation. The Schiff base derivative from dehydroabietylamine and (substituted) benzaldehyde according to the present invention can effectively inhibit Botrytis cinerea, Fusarium solani, Fusarium graminearum, Fusarium oxysporum, Alternaria brassicicola, Coriolus versicolor and the like, and therefore, can be used directly in the wood preservation or can be used in the manufacture of a wood preservative. The Schiff base derivative from dehydroabietylamine and (substituted) benzaldehyde has such advantages as wide source of raw materials, low cost, being natural, non-toxic and renewable. *u 50 20-+ 10 Botrytis cinerea Y 8 0 •I .1 1 . 0 20 40 60 80 100 Concentration C /gg/mL

Description

Use of Schiff Base Derivative from Dehydroabietylamine and (Substituted) Benzaldehyde

Technical Field

The present invention relates to the use of a Schiff base derivative from dehydroabietylamine and (substituted) benzaldehyde, and belongs to the field of wood preservation.

Background

Wood, as a renewable biomass material, has the characteristics such as being non-toxic, pollution-free, aesthetically pleasing and easy to process. It has been widely used in construction and decoration materials, and is a green natural product which is favored by people. However, the wood is rich in cellulose that provides nutrients for wood-decaying fungi under the conditions of appropriate temperature and humidity, which makes the wood susceptible to decay by the invasion of insects and fungi, leading to a shortened service life of the wood, and loss in terms of economic value and use value of the wood. Therefore, preservative treatment of wood is an important way and means to prolong the service life of wood, improve the level of wood utilization and save wood resources. Hence, the research and development of technologies such as wood preservation have been receiving wide attention.

In the prior art, there are many types of wood preservatives, but they generally have relatively high toxicity, and therefore, will cause serious environmental pollution and safety problems, and even cause poisoning of human and livestock, while preserving the wood, which limits their application. In contrast, natural wood preservatives have the advantages such as lower toxicity, less pollution, uniform dispersion in wood, not easy to lose, recyclability of bioactive substances, and good preservative and antimicrobial performance. Therefore, the research of natural wood preservatives is of great significance to improve the safety and environmental friendliness of wood products.

Summary

The present invention provides the use of a Schiff base derivative from dehydroabietylamine and (substituted) benzaldehyde for effectively inhibiting Botrytis cinerea, Fusarium solani, Fusarium graminearum, Fusarium oxysporum, Alternaria brassicicola, Coriolus versicolor and the like, and thus for wood preservation. The Schiff base derivative from dehydroabietylamine and (substituted) benzaldehyde is prepared from rosin which is a renewable resource, and therefore, has the advantages such as being natural, non-toxic and renewable.

The present invention solves the above technical problems by the following technical solutions.

The present invention provides the use of a Schiff base derivative from dehydroabietylamine and (substituted) benzaldehyde for wood preservation.

Microbial inhibitors are highly selective for species, and the same product has significantly different inhibitory effects on different species. As a result of intensive studies, the applicant found that the Schiff base derivative from dehydroabietylamine and (substituted) benzaldehyde can effectively inhibit Botrytis cinerea, Fusarium solani, Fusarium graminearum, Fusarium oxysporum, Alternaria brassicicola, Coriolus versicolor and the like, and therefore can be used for wood preservation.

The above-mentioned Schiff base derivative from dehydroabietylamine and (substituted) benzaldehyde can be directly used for the wood preservation, and can also be used for preparing a wood preservative.

In order to improve the preservative effect, the Schiff base derivative from dehydroabietylamine and (substituted) benzaldehyde is used at a concentration of 11.25-180 pg/mL. Through a large number of studies, the applicant found that the concentration of the Schiff base derivative from dehydroabietylamine and (substituted) benzaldehyde is often not simply proportional to the microbial inhibitory effect. As the concentration increases, the microbial inhibition rate will first increase, then decrease, and finally increase again.

2019101540 09 Dec 2019

The above-mentioned Schiff base derivative from dehydroabietylamine and (substituted) benzaldehyde has the following structural formula:

ensure the effect of wood preservation, preferably, R2 is

The above-mentioned different Schiff base derivatives from dehydroabietylamine and (substituted) benzaldehyde can also be used for inhibiting specific pathogenic firngi to be suitable for the requirements of different situations, wherein the Schiff base derivative from dehydroabietylamine and (substituted) benzaldehyde, in which R2 is

is used for inhibiting Botrytis cinerea and Fusarium graminearum; the Schiff base derivative from dehydroabietylamine and (substituted) benzaldehyde, in which R2 is

HjCO

or

is used for inhibiting Botrytis cinerea, Fusarium solani,

Alternaria brassicicola, Fusarium graminearum and Fusarium oxysporum; the Schiff base

OH derivative from dehydroabietylamine and (substituted) benzaldehyde, in which R2 is , is used for inhibiting Botrytis cinerea, Alternaria brassicicola and Fusarium graminearum’, the

Schiff base derivative from dehydroabietylamine and (substituted) benzaldehyde, in which R2

is used for inhibiting Botrytis cinerea and Alternaria brassicicola’, the Schiff base derivative from dehydroabietylamine and (substituted) benzaldehyde, in which R2 is

, is used for inhibiting Botrytis cinerea and Alternaria brassicicola’, and the Schiff

2019101540 09 Dec 2019 base derivative from dehydroabietylamine and (substituted) benzaldehyde, in which R₂ is

, is used for inhibiting Botrytis cinerea and Fusarium graminearum.

In order to further improve the effect of wood preservation, in the structural formula of the above-mentioned Schiff base derivative from dehydroabietylamine and (substituted)

OH

and more preferably, . The Schiff base derivative from benzaldehyde, further preferably, R₂ is OH o₂nhTV , F

OH „ · ci

R₂ is dehydroabietylamine and (substituted) benzaldehyde, in which R₂ is

Cl

, has 100% inhibition rate against both Botrytis cinerea and Alternaria brassicicola. The Schiff base derivative from dehydroabietylamine and (substituted) benzaldehyde, in which R₂ is

, has 100% inhibition rate against Fusarium solani and Alternaria brassicicola.

The Schiff base derivative from dehydroabietylamine and (substituted) benzaldehyde, in which

, also achieves 100% inhibition rate against some pathogenic fungi. Even more preferably, R₂ is

Taking in consideration of both cost and microbial inhibition efficiency, it is preferable that the Schiff base derivative from dehydroabietylamine and (substituted) benzaldehyde, in which R₂ is

OH

, is used at a concentration of 11.25±2 pg/mL. The Schiff base derivative from dehydroabietylamine and (substituted) benzaldehyde, in which R₂ is F' is used at a concentration of 22.5±2 pg/mL. The Schiff base derivative from dehydroabietylamine and (substituted) benzaldehyde, in which R2 is , j_{s use}j _at _a concentration of 11.25±2 pg/mL. The Schiff base derivative from dehydroabietylamine and / \__ (substituted) benzaldehyde, in which R₂ is , is used at a concentration of 45±2 pg/mL. In other words, the substitution position and type of halogen atom on the benzene ring have an influence on the optimal concentration of microbial inhibitory activity. The abovementioned Schiff base derivative from dehydroabietylamine and (substituted) benzaldehyde can be directly used for the wood preservation after being diluted, and also can be used as an active ingredient for preparing a wood preservative after being formulated with other substances.

For the technologies not mentioned in the present invention, reference is made to the prior art.

The Schiff base derivative from dehydroabietylamine and (substituted) benzaldehyde according to the present invention can effectively inhibit Botrytis cinerea, Fusarium solani, Fusarium graminearum, Fusarium oxysporum, Alternaria brassicicola, Coriolus versicolor and the like. Therefore, the Schiff base derivative from dehydroabietylamine and (substituted) benzaldehyde according to the present invention can be directly used for the wood preservation or for the preparation of a wood preservative. The Schiff base derivative from dehydroabietylamine and (substituted) benzaldehyde has such advantages as wide source of raw materials, low cost, being natural, non-toxic and renewable.

Brief Description of the Drawings

FIG. 1 is a graph showing the inhibitory activity of the Schiff base derivative from dehydroabietylamine and (substituted) benzaldehyde against Botrytis cinerea at different concentrations;

FIG. 2 is a graph showing the inhibitory activity of the Schiff base derivative from dehydroabietylamine and (substituted) benzaldehyde against Fusarium solani at different concentrations;

FIG. 3 is a graph showing the inhibitoiy activity of the Schiff base derivative from dehydroabietylamine and (substituted) benzaldehyde against Fusarium graminearum at different concentrations;

FIG. 4 is a graph showing the inhibitoiy activity of the Schiff base derivative from dehydroabietylamine and (substituted) benzaldehyde against A Itemaria brassicicola at different concentrations;

FIG. 5 is a graph showing the inhibitoiy activity of the Schiff base derivative from dehydroabietylamine and (substituted) benzaldehyde against Fusarium oxysporum at different concentrations; and

FIG. 6 is a graph showing the inhibitory activity of the Schiff base derivative from dehydroabietylamine and (substituted) benzaldehyde against Coriolus versicolor at different concentrations.

Detailed Description of the Embodiments

In order to better understand the present invention, the content of the present invention is further clarified below with reference to the examples, but the content of the present invention is not limited to the following examples.

1. Samples: Schiff base derivatives from dehydroabietylamine and (substituted) benzaldehyde, having the following structural formula: +Ή₂ΝCH-R_{2 For conven}i_ence, the samples of the Schiff base derivatives from dehydroabietylamine and (substituted) benzaldehyde were numbered according to R₂, as shown in Table 1 below.

Table 1. Numbering of the Schiff base derivatives from dehydroabietylamine and (substituted) benzaldehyde.

2019101540 09 Dec 2019

Sample No.	r₂
1
2	Η,ΟΟ-θ-
3	pH
4	OH
5	OH
6	F
7
8	_____^a-Q-_____
9	_____^F3^C A A

2. Pathogenic fungi: The representative pathogenic fungi that are liable to cause wood decay were selected, including Botrytis cinerea (CGMCC 3.3790), Fusarium solani (CGMCC 3.2889), Fusarium graminearum (CGMCC3.4733), Fusarium oxysporum (CGMCC 3.3633), Altemaria brassicicola (CGMCC 3.7805) and Coriolus versicolor (CFCC5336). The above 6 tested plant pathogenic fungi were provided by China General Microbiological Culture Collection Center and China Forestry Culture Collection Center.

3. Other reagents. Anhydrous ethanol, dextrose, agar and actidione were all analytically pure.

4. Preparation of culture medium:

Preparation of Potato Dextrose Agar (PDA) Medium: 200 g of potatoes were accurately weighed, washed and peeled. Subsequently, the potatoes were cut into small pieces and poured into 1000 ml of boiling distilled water (at 100°C) and cooked, while stirring continuously to prevent sticking to the pan. After the potatoes were cooked until they were crushed by gentle pressing, the potato residue was filtered off to obtain the potato filtrate. After that, the potato filtrate was heated to boiling with a low heat, 20 g of dextrose was added, and the mixture was stirred until the dextrose was completely dissolved. Subsequently, 18 g of agar was added and stirred to prevent sticking to the pan, and then, the heat was reduced. When the liquid was clear and transparent, the heat was turned off to obtain the PDA medium.

5. Activation of pathogenic fungi:

(1) Sterilization: The cleaned Petri dishes, inoculation needles, PDA medium and the like were put into an autoclave (HVE-50 autoclave, Hua Yue Enterprise Holdings Ltd.) and sterilized at 0.1 Mpa and 121 °C for 22 min.

(2) Preparation of plates: The sterilized medium and appliances were put into a clean bench (SW-CJ-1FD clean bench, Suzhou Antai Airtech Co., Ltd) and irradiated with UV light for 15 minutes, followed by turning off the UV light and blowing for 10 minutes The unsolidified medium was poured into empty dishes at about 20 mL per dish and placed horizontally, and then inoculated after being completely cooled and solidified. The dishes were marked with the name of inoculum and the date of inoculation.

(3) Inoculation: The mycelia of the pathogenic fungi stored in test tubes were picked out with the inoculation needles, and plated on the plates by streak method. Note that the agar should not be broken. After the inoculation was completed, the dishes were sealed with a parafilm to prevent the entry of foreign contaminants.

(4) Culture: The inoculated fungal plates were placed in an incubator (PQX-380D multisegment programmable artificial climate chamber (incubator), Ningbo Dongnan Instrument Co., Ltd.) at 28 C and incubated while protecting from light, until there were obvious colonies.

6. Determination of microbial inhibitory activity of each sample:

6.1 Preliminary determination of microbial inhibitory activity. The following procedures were performed for each sample.

mg of the sample was accurately weighed and made up to 10 mL with anhydrous ethanol to formulate a sample solution to be tested having a concentration of 3.6 mg/mT. The final concentration of the sample in each dish was set to 180 pg/mL. Anhydrous ethanol was used as a solvent control. An aqueous solution of actidione with the same concentration as the sample solution to be tested was used as a positive control. The PDA medium alone was used as a blank control. The inhibitory activity of the sample solution to be tested against the pathogenic fungi was determined by growth rate method.

In the clean bench, 9 mL of the sample solution to be tested was transferred with a sterilized pipette tip and filtered over a 0.22 pm sterile filter, and then mixed with 171 mL of PDA medium at 40 C under gentle shaking until homogeneous, to afford PDA medium containing the sample (180 pg/mL). 10 mL of the PDA medium containing the sample was poured into each of the dishes. After that, the dishes were rotated to evenly spread the medium, and marked, followed by cooling and solidifying the medium for future use. The same procedures as described above were performed for the solvent control and the positive control.

The obtained dishes were inoculated with the respective pathogenic fungi already activated. All of the pathogenic fungi were inoculated on the same day. After the inoculation, the dishes were placed in the incubator and incubated for 10 days, during which on Day 2, 4, 6, 8 and 10, the colony growth diameters of the pathogenic fungi were measured by cross method. The data were recorded and the results are shown in Table 2. The inhibition rate was calculated according to the following equation:

Inhibition rate (% IR)=[(Mean diameter of blank control group)-(Mean diameter of treatment group)]/(Mean diameter of blank control group) x 100%

Table 2. Preliminary determination of microbial inhibitory activity of Schiff base derivative from dehydroabietylamine and (substituted) benzaldehyde.

Botrytis cinerea

Sample Growth days of pathogenic fungus No. 2d 4d 6d 8dlOd

J 95.19 94.09 94.69 94.6992.45 % % % %% ₂ 93.27 95.91 95.71 93.4791.02 % % % %% ₃ 96.39 87.73 81.94 71.2265.38 % % % % % ___Fusarium solani__ Growth days of pathogenic fungus

2d	4d	6d	8d	lOd
68.52	77.44	84.52	84.20	79.60
%	%	%	%	%
88.89	95.11	94.29	94.20	91.00
%	%	%	%	%
86.11	81.58	72.14	65.20	50.60
%	%	%	%	%

2019101540 09 Dec 2019 ίο

4	100.0	100.0	100.0	100.0	100.0	88.89	76.69	69.52	64.40	51.80
	0%	0%	0%	0%	0%	%	%	%	%	%
5	98.56	93.41	85.92	76.53	70.41	53.70	54.51	52.38	42.20	24.20
	%	%	%	%	%	%	%	%	%	%
6	100.0	98.64	93.88	90.00	84.29	28.70	52.63	59.52	57.20	48.60
	0%	%	%	%	%	%	%	%	%	%
7	100.0	100.0	100.0	92.24	95.10	100.0	96.99	96.90	97.00	96.20
	0%	0%	0%	%	%	0%	%	%	%	%
8	100.0	100.0	97.14	97.14	95.10	100.0	100.0	100.0	100.0	100.0
	0%	0%	%	%	%	0%	0%	0%	0%	0%
9	96.15	94.55	94.29	89.39	88.78	67.59	72.93	79.05	77.60	76.00
	%	%	%	%	%	%	%	%	%	%
Positive	100.0	100.0	100.0	100.0	100.0	100.0	100.0	100.0	100.0	100.0
control	0%	0%	0%	0%	0%	0%	0%	0%	0%	0%
		Altemaria brassicicola			Fusarium eraminearum
Sample	Growth days of pathogenic fungus	Growth days of pathogenic fungus
No.	2d	4d	6d	8d	lOd	2d	4d	6d	8d	lOd
1	66.67	72.05	61.65	61.62	54.38	82.98	84.87	81.18	86.59	87.12
	%	%	%	%	%	%	%	%	%	%
2	89.58	90.83	90.27	89.25	86.88	87.23	84.87	82.80	83.91	81.29
	%	%	%	%	%	%	%	%	%	%
3	90.63	89.08	88.20	87.72	83.54	93.62	82.35	80.65	77.78	81.60
	%	%	%	%	%	%	%	%	%	%
4	100.0	100.0	100.0	100.0	100.0	91.49	85.71	72.58	68.58	66.87
	0%	0%	0%	0%	0%	%	%	%	%	%
5	95.83	95.63	93.51	94.74	94.79	38.30	31.93	24.73	25.67	24.23
	%	%	%	%	%	%	%	%	%	%
6	87.50	82.97	74.78	72.37	65.94	91.49	90.76	82.80	80.08	76.38
	%	%	%	%	%	%	%	%	%	%
7	100.0	93.45	92.04	90.79	86.25	100.0	89.92	89.25	92.34	91.41
	0%	%	%	%	%	0%	%	%	%	%
8	100.0	100.0	100.0	100.0	100.0	87.23	89.92	83.87	86.97	86.50
	0%	0%	0%	0%	0%	%	%	%	%	%
9	72.92	81.66	84.07	85.96	85.00	55.32	53.78	56.45	51.34	49.39
	%	%	%	%	%	%	%	%	%	%
Positive	100.0	100.0	100.0	100.0	100.0	100.0	100.0	100.0	100.0	100.0
control	0%	0%	0%	0%	0%	0%	0%	0%	0%	0%
		Fusarium oxysporum			Coriolus versicolor
Sample	Growth days of pathogenic fungus	Growth days of pathogenic fungus
No.	2d	4d	6d	8d	lOd	2d	4d	6d	8d	lOd
1	81.73	61.16	58.42	53.80	39.80	19.40	37.65	38.55	34.62	31.46
	%	%	%	%	%	%	%	%	%	%
2	80.77	80.58	83.68	84.60	81.60	53.73	69.41	71.37	67.16	63.17
	%	%	%	%	%	%	%	%	%	%
3	94.23	87.60	73.16	73.60	67.60	55.22	53.53	51.53	45.56	40.73

2019101540 09 Dec

%	%	%	%	%
80.77	51.24	52.11	48.60	39.40
%	%	%	%	%
30.77	33.88	35.26	33.20	16.00
%	%	%	%	%
73.08	87.60	73.16	73.60	67.60
%	%	%	%	%
77.88	88.43	91.05	91.80	90.00
%	%	%	%	%
88.46	91.32	94.47	95.80	95.80
%	%	%	%	%
46.15	61.16	58.42	53.80	39.80
%	%	%	%	%

%	%	%	%	%
86.57	94.71	75.95	72.49	68.29
%	%	%	%	%
19.40	32.35	33.97	32.84	31.95
%	%	%	%	%
55.22	53.53	51.53	45.56	40.73
%	%	%	%	%
29.85	54.12	68.32	70.41	71.22
%	%	%	%	%
49.25	62.35	60.31	61.54	61.95
%	%	%	%	%
19.40	37.65	38.55	34.62	31.46
%	%	%	%	%

Positive 100.0 84.30 77.37 73.40 63.20 control 0% % % % %

100.0 100.0 93.89 80.47 75.61

0% 0% % % %

The percentages in Table 2 above are inhibition rates. From Table 2, it is shown that the Schiff base derivatives from dehydroabietylamine and (substituted) benzaldehyde each had relatively good inhibitory activity against these six pathogenic fungi and can be used for wood preservation. After 2 days, the inhibition rates of Sample No. 1 against Botrytis cinerea and 5 Fusarium graminearum were greater than 90% and greater than 80%, respectively. Sample Nos.

2, 7 and 8 each had inhibition rates greater than 80% against Botrytis cinerea, Fusarium solani, Alternaria brassicicola, Fusarium graminearum and Fusarium oxysporum, and therefore had outstanding microbial inhibitory activity. The inhibition rates of Sample No. 8 against Fusarium solani and Alternaria brassicicola both were 100%, which was comparable to the inhibitory 10 activity of actidione as positive control against Fusarium solani and Alternaria brassicicola.

The inhibition rates of Sample No. 4 against Botrytis cinerea and Alternaria brassicicola both were 100%, which was comparable to the inhibitoiy activity of actidione against Botrytis cinerea and Alternaria brassicicola.

6.2 Further determination of microbial inhibitory activity:

The above-mentioned Schiff base derivatives from dehydroabietylamine and (substituted) benzaldehyde having better inhibitory activity against the six different pathogenic fungi, namely Sample Nos. 4 and 6-8, were selected for further determination. The following procedures were performed for each sample. Sample solutions were prepared at a final sample concentration of 100, 50, 25, and 12.5 pg/mL in each dish using a two-fold serial dilution method. Also, anhydrous ethanol was used as a solvent control. An aqueous solution of actidione with the same concentration as the sample solution to be tested was used as a positive control. The PDA medium alone was used as a blank control. Under the concentration gradient, the same sample was inoculated with each of six pathogenic fungi, including Botrytis cinerea, Coriolus versicolor, Fusarium solani, Fusarium oxysporum, Alternaria brassicicola, and Fusarium graminearum. Three replicates were set up for each experiment. The dishes were incubated in the incubator at 28°C for 10 days, during which the growth diameter of each of the pathogenic fungi was measured, and the mean diameter and inhibition rate were calculated. The results are shown in Figs. 1-6, in which 4, 6, 7 and 8 represent Sample No. 4, Sample No. 6, Sample No. 7 and Sample No. 8, respectively.

As shown in Figs. 1-6, the four samples had excellent inhibitory activities against these six different pathogenic fungi at different concentrations. Sample No. 4 at 11.25 pg/mL had the highest inhibition rates against the six different pathogenic fungi. Sample No. 6 at 22.5 pg/mL had the highest inhibition rates against the six different pathogenic fungi, all of which were greater than 95%. By comprehensive analysis of the inhibition rates of Sample No. 7 against the six different pathogenic fungi, it was preferred at about 11.25 pg/mL, and the inhibition rates were lowest at 25 pg/mL. Sample No. 8 at 45 pg/mL had the highest inhibition rates against the six different pathogenic fungi.

Claims

Claims

What is claimed is:

1. Use of a Schiff base derivative from dehydroabietylamine and (substituted) benzaldehyde, in wood preservation or in the manufacture of a wood preservative.
2. The use of the Schiff base derivative from the dehydroabietylamine and the (substituted) benzaldehyde according to claim 1, wherein the Schiff base derivative from the dehydroabietylamine and the (substituted) benzaldehyde is used at a concentration of 11.25-180 pg/mL.
3. The use of the Schiff base derivative from the dehydroabietylamine and the (substituted) benzaldehyde according to claim 1 or 2, wherein the Schiff base derivative from the dehydroabietylamine and the (substituted) benzaldehyde has the following structural formula:
4. The use of the Schiff base derivative from the dehydroabietylamine and the (substituted) benzaldehyde according to claim 3, wherein the Schiff base derivative from the dehydroabietylamine

QH

OH

Cl

and the (substituted) benzaldehyde, in which R.2 is

, is used for inhibiting Botrytis cinerea and Fusarium graminearum; the Schiff base derivative from the dehydroabietylamine and the

HjCO-vF—4p— Cl— (substituted) benzaldehyde, in which R2 is , ? or , is used for inhibiting Botrytis cinerea, Fusarium solani, Alternaria brassicicola, Fusarium graminearum and Fusarium oxysporum; the Schiff base derivative from the dehydroabietylamine and the (substituted) benzaldehyde, in which R2 is

OH

is used for inhibiting Botrytis cinerea,

Alternaria brassicicola and Fusarium graminearum', the Schiff base derivative from the

2019101540 09 Dec 2019 dehydroabietylamine and the (substituted) benzaldehyde, in which R2 is

OH

Cl

, is used for inhibiting Botrytis cinerea and Alternaria brassicicolcr, the Schiff base derivative from the dehydroabietylamine and the (substituted) benzaldehyde, in which R2 is o₂n

OH

is used for inhibiting Botrytis cinerea and Alternaria brassicicokr, and the Schiff base derivative from the

dehydroabietylamine and the (substituted) benzaldehyde, in which R2 is F , is used for inhibiting Botrytis cinerea and Fusarium graminearum.
5. The use of the Schiff base derivative from the dehydroabietylamine and the (substituted) benzaldehyde according to claim 3, wherein R₂ is

OH

; the Schiff base derivative from the dehydroabietylamine and the (substituted) benzaldehyde, in which R2 is

OH

is used at a concentration of 11.25±2 gg/mL; the Schiff base derivative from the dehydroabietylamine and the (substituted) benzaldehyde, in which R2 is

, is used at a concentration of 22.5±2 gg/mL; the Schiff base derivative from the

dehydroabietylamine and the (substituted) benzaldehyde, in which R2 is , is used at a concentration of 11.25±2 gg/mL; and the Schiff base derivative from the dehydroabietylamine and

Cl the (substituted) benzaldehyde, in which R2 is gg/mL.

, is used at a concentration of 45±2