CN101288402A - New use of aza chalcones compound as agricultural bactericidal agent - Google Patents

Abstract

The invention provides a new use that nitrogen heterocyclic chalcone compound is used as an agricultural fungicide, that is a new use of nitrogen heterocyclic chalcone compound. In the invention, the nitrogen heterocyclic chalcone compound is used for studying the activity of pathogenic bacteria of various plants, thus proving that the nitrogen heterocyclic chalcone compound has good inhibitory effect on pathogenic bacteria and epiphyte of plants, thus providing a novel green pesticide with steadiness, high efficiency and innocuity for the field of pesticide.

Description

Aza chalcones compound is as the new purposes of disinfectant use in agriculture

Technical field

What the present invention relates to is the new purposes of aza chalcones compound as disinfectant use in agriculture, belongs to pesticide field.

Background technology

According to statistics, the main kind more than 300 of corps diseases of China's discovery at present, wherein more than 70 kind of rice disease, more than 50 kind of wheat diseases, more than 30 kind of maize diseases, more than 50 kind of soybean diseases, more than 30 kind of sunflower disease, more than 30 kind of rape disease, more than 30 kind of beet disease etc.About 8,660 ten thousand hm of China's long-term crop pest generation area ², the control area accounts for 80%～90% of area, about 6,700 ten thousand hm of the chemical control gross area takes place ², more than 50 of applying bactericidal agent kinds, preparation is kind more than 410, and about 3.6 ten thousand tons of consumption accounts for more than 13% of the total consumption of agricultural chemicals.Because chemical bactericide has characteristics such as preventive effect is obvious, speed is fast, cost is low, easy to use, therefore the main means of controlling plant diseases are the use chemical bactericide at present.

Aza chalcones compound is the structure optimization product that derives from the chalcone compounds with extensive medicinal activity that extensively is present in occurring in nature.Aspect medical, have many physiology and pharmacologically active, as antibacterial activity [FR2357247 (1978), Acta Facultatis PharmaceuticaeBohemoslovenicae (1966,12,89-129), Indian Journal of Chemistry (1963,1,484-6), US6677350, DE1931204], antiphlogistic activity [Bioorganic ﹠amp; Medicinal ChemistryLetters (2004,10,2559-2562), Bioorganic ﹠amp; Medicinal Chemistry (2002,10,4035-4041)], resistive connection nuclear activity [Chemical ﹠amp; Pharmaceutical Bulletin (2007,55,44-49)], active anticancer [Chemical ﹠amp; Pharmaceutical Bulletin (1970,18,1408-13)], anthelmintic activity [Canadian Journal of Pharmaceutical Sciences (1967,2,37-43)], as sedative [JP45014790].

Yet up till now for this reason, yet there are no the report of aza chalcones compound as agricultural antibacterial agent.

Summary of the invention

The objective of the invention is to expand the purposes of aza chalcones compound, the new purposes of aza chalcones compound as disinfectant use in agriculture is provided.

Described aza chalcones compound is meant to have the compound shown in the following general formula (I):

(I) A is in the formula:

B is:

Wherein R is hydrogen, halogen, methyl, methoxyl group, cyano group, trifluoromethyl, nitro, amino, hydroxyl.

Further, the invention provides the purposes of aza chalcones compound as bactericide.

Wherein said purposes is that control is by bacterium or fungus-caused plant disease.

The inventor furthers investigate the activity that aza chalcones compound suppresses the various plants pathogen, experimental result finds that aza chalcones compound has good inhibitory effect to phytopathogen, provides a kind of new thinking for the aza chalcones compound exploitation is become a kind of new environment friendly agricultural.

Below, foregoing of the present invention is described in further detail again by embodiment.But this should be interpreted as it is limitation of the present invention.

Embodiment

The aza chalcones compound of following examples all derives from Sichuan University's agricultural chemicals and crop protection research institute, and the test plant pathogen derives from Sichuan University, Chengdu Inst. of Biology, Chinese Academy of Sciences, Chinese common micro-organisms DSMZ and Sichuan Academy of Agricultural Sciences.

Embodiment 1 compound Preparation

With the 2-acetylpyridine (15mmol 1.82g) is dissolved in the 20ml ethanol, add furfural (15mmol, 1.44g).The NaOH solution of adding 5% stirs under continuous stirring condition.Continue at ambient temperature to stir after 6-8 hour, after adding 100ml water dilutes, have faint yellow solid to separate out, suction filtration goes out solid, and the washing solid is to neutral, and infrared oven dry is recrystallized with ethyl acetate and benzinum, promptly.

¹H-NMR(400MHz，CDCl ₃)：δ6.51-6.52(1H，m)，6.77(1H，d，J＝3.6Hz)，7.46-7.49(1H，m)，7.54(1H，d，J＝0.4Hz)，7.70(1H，d，J＝15.6Hz)，7.85-7.89(1H，m)，8.13(1H，d，J＝16.0Hz)，8.18(1H，s)，8.74(1H，d，J＝4.4Hz).

Embodiment 2 compounds Preparation

With the 3-acetylpyridine (15mmol 1.82g) is dissolved in the 20ml ethanol, add furfural (15mmol, 1.44g).The NaOH solution of adding 5% stirs under continuous stirring condition.Continue at ambient temperature to stir after 6-8 hour, after adding 100ml water dilutes, have faint yellow solid to separate out, suction filtration goes out solid, and the washing solid is to neutral, and infrared oven dry is recrystallized with ethyl acetate and benzinum, promptly.

¹H-NMR(400MHz，CDCl ₃)：δ6.54-6.55(1H，m)，6.78(1H，d，J＝3.2Hz)，7.41(1H，d，J＝15.2Hz)，7.45-7.47(1H，m)，7.56(1H，d，J＝1.6Hz)，7.63(1H，d，J＝15.2Hz)，8.28-8.31(1H，m)，8.79-8.80(1H，m)，9.24(1H，d.J＝2.0Hz).

Embodiment 3 aza chalcones compounds are measured 1 test plant pathogen to the bactericidal activity of plant pathogenetic bacteria and fungi

1.1 test plant pathogenetic bacteria

Xanthomonas oryzae (Xanthomonas oryzae pv.oryzae), cotton angular leaf spot fungus (Xanthomonascampestris pv.malvacearum), tobacco ralstonia solanacearum (Pseudomonas solanacearum pv.tabaci), corn bacterial wilt (Pantoea stewartii subsp.stewartii), cabbage black rot bacterium (Xanthomonas campestris pv.Campestris), potato rot positive germ (Erwinia carotovorasubsp.carotovora), ginger ginger plague germ (Ralstonia solanacearum), soft rot of cabbage bacterium (Erwinia aroideae).

1.2 test plant disease fungus

Pyricularia oryzae (Piricularia oryzae Cav), fusarium graminearum (Fusarium graminearum), Rhizoctonia solani Kuhn (Rhizoctonia solani), cotton rhizoctonia solani (Thanatephorus cucumeris), Exserohilum turcicum (Exserohilum turcicum), southern corn leaf blight (Bipolaris maydis), peanut Cercospora bacteria (Cercosporaarachidicola), Chinese cabbage alternaria (Alternaria brassicae), phytophthora infestans (Phytophthora infestans), anthracnose of tobacco bacterium (Colletotrichum nicotianae), botrytis cinerea (Botrytis cirerea).

2 experimental techniques

2.1 aza chalcones compound is measured the bacteriostatic activity of plant pathogenetic bacteria

Adopt growth rate method to measure bacterium colony inhibiting rate (%):

Respectively 1.1 described plant pathogenetic bacterias are diluted to finite concentration, join (ultimate density of aza chalcones compound adopts the test tube doubling dilution to make a series of aza chalcones compound concentration gradient medium) in the aza chalcones compound liquid nutrient medium, each series inoculation is a kind of for examination bacterium suspension, each concentration is done 3 repeating groups, and makes blank with sterile water.After cultivating 18-24 hour under 35-38 ℃, these a series of cultures are carried out the bacterium numeration with the gradient dilution method, ask the bacterium colony inhibiting rate according to clump count, formula is as follows:

2.2 aza chalcones compound is measured the bacteriostatic activity of plant pathogenic fungi

Toxic medium therapy is measured mycelia relative inhibition (%):

At first aza chalcones compound with after the sterile water dilution again with PDA medium mixing, the ultimate density of aza chalcones compound adopts doubling dilution, make the uniform pastille flat board of a series of thickness, use sterile water as blank, reprocessing 3 times.After culture medium solidifying, plant pathogenic fungi is connected on the medium that solidifies for examination bacterium cake, to cultivate 3-5 days at 27-28 ℃, bacterium cake diameter is 0.4cm, measures colony diameter with the right-angled intersection method, calculates mycelial growth inhibition rate.

3 experimental results

Aza chalcones compound to the bacteriostatic activity measurement result of described plant pathogenetic bacteria see Table 1, table 2 and table 3.By table 1, table 2 and table 3 result as can be known, aza chalcones compound all has good inhibitory effect to plant pathogenetic bacteria.

Table 1 embodiment 1 compound when 50mg/L to the relative inhibition (%) of plant pathogenetic bacteria

Bacterial classification	Bacterium colony inhibiting rate (%)	Bacterial classification	Bacterium colony inhibiting rate (%)
				Xanthomonas oryzae	100	The cotton angular leaf spot fungus	98.36
The corn bacterial wilt	89.30	Tobacco ralstonia solanacearum	97.85
				The potato rot positive germ	75.60	The soft rot of cabbage bacterium	100
The cabbage black rot bacterium	78.68	Ginger ginger plague germ	85.36

Table 2 embodiment 2 compounds when 50mg/L to the relative inhibition (%) of plant pathogenetic bacteria

Bacterial classification	Bacterium colony inhibiting rate (%)	Bacterial classification	Bacterium colony inhibiting rate (%)
				Xanthomonas oryzae	100	The cotton angular leaf spot fungus	93.56
The corn bacterial wilt	88.32	Tobacco ralstonia solanacearum	95.47
				The potato rot positive germ	73.56	The soft rot of cabbage bacterium	100
The cabbage black rot bacterium	77.78	Ginger ginger plague germ	79.20

Table 3 embodiment 3 compounds when 50mg/L to the relative inhibition (%) of plant pathogenetic bacteria

Bacterial classification	Bacterium colony inhibiting rate (%)	Bacterial classification	Bacterium colony inhibiting rate (%)
				Xanthomonas oryzae	100	The cotton angular leaf spot fungus	97.65
The corn bacterial wilt	84.36	Tobacco ralstonia solanacearum	91.48
				The potato rot positive germ	79.38	The soft rot of cabbage bacterium	100
The cabbage black rot bacterium	78.83	Ginger ginger plague germ	58.48

Below be aza chalcones compound to the inhibition determination of activity result of plant pathogenic fungi (see Table 4, table 5 and table 6).By table 4, table 5 and table 6 result as can be known, aza chalcones compound also has good inhibitory effect to plant pathogenic fungi.

Table 4 embodiment 1 compound is at the relative inhibition (%) of 50mg/L to plant pathogenic fungi

Bacterial classification	Relative inhibition (%)	Bacterial classification	Relative inhibition (%)
				Pyricularia oryzae	90.30	Rhizoctonia solani Kuhn	100
Exserohilum turcicum	86.34	Fusarium graminearum	59.61
				Southern corn leaf blight	78.36	Peanut Cercospora bacteria	96.38
Cotton rhizoctonia solani	89.67	The Chinese cabbage alternaria	69.38
				Phytophthora infestans	62.35	Botrytis cinerea	81.67
The anthracnose of tobacco bacterium	79.68

Table 5 embodiment 2 compounds are at the relative inhibition (%) of 50mg/L to plant pathogenic fungi

Bacterial classification	Relative inhibition (%)	Bacterial classification	Relative inhibition (%)
				Pyricularia oryzae	87.36	Rhizoctonia solani Kuhn	100
Exserohilum turcicum	85.46	Fusarium graminearum	50.14
				Southern corn leaf blight	70.34	Peanut Cercospora bacteria	94.67
Cotton rhizoctonia solani	88.46	The Chinese cabbage alternaria	70.92
				Phytophthora infestans	60.36	Botrytis cinerea	78.49
The anthracnose of tobacco bacterium	80.67

Table 6 embodiment 3 compounds are at the relative inhibition (%) of 50mg/L to plant pathogenic fungi

Bacterial classification	Relative inhibition (%)	Bacterial classification	Relative inhibition (%)
				Pyricularia oryzae	96.37	Rhizoctonia solani Kuhn	100
Exserohilum turcicum	90.27	Fusarium graminearum	75.46
				Southern corn leaf blight	73.30	Peanut Cercospora bacteria	100
Cotton rhizoctonia solani	86.26	The Chinese cabbage alternaria	84.39
				Phytophthora infestans	71.48	Botrytis cinerea	76.12
The anthracnose of tobacco bacterium	87.56

In sum, aza chalcones compound of the present invention has broad-spectrum sterilization activity preferably to phytopathogen, its exploitation is become have stable, efficient, nontoxic novel green agricultural chemicals, has bright prospects.

Claims (3)

1, aza chalcones compound is as the new purposes of disinfectant use in agriculture.

2, new purposes according to claim 1 is characterized in that described aza chalcones compound is meant to have the compound shown in the following general formula (I):

(I) A is in the formula:

B is:

Wherein R is hydrogen, halogen, methyl, methoxyl group, cyano group, trifluoromethyl, nitro, amino, hydroxyl.

3, new purposes according to claim 1 is characterized in that the purposes of the described purposes plant disease that to be aza chalcones compound cause the control plant pathogenic fungi.