CN112106774A - Application of dicarboxylic acid compound in preventing and treating plant diseases - Google Patents
Application of dicarboxylic acid compound in preventing and treating plant diseases Download PDFInfo
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- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
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- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
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Abstract
The invention discloses an application of dicarboxylic acid compounds in preventing and treating plant diseases; the dicarboxylic acid compound is selected from compounds shown in formulas I, II, III and IV, and isomers, hydrates or salts thereof. The dicarboxylic acid compound has obvious effect on inhibiting the activity of fungus or oomycete appressorium formation, can be used for preventing and controlling rice blast, anthracnose, downy mildew, phytophthora root rot, gray mold and the like, has no obvious phytotoxicity and has good safety. Compared with the existing compounds for controlling plant diseases such as rice blast, anthracnose, downy mildew, phytophthora root rot, gray mold and the like, the dicarboxylic acid compound has the characteristics of good prevention effect, environmental protection, no toxicity, low residue and safety.
Description
Technical Field
The invention relates to a new application of dicarboxylic acid compounds, in particular to an application of the compounds in controlling plant diseases.
Background
The dicarboxylic acid compounds shown in the formulas I, II, III and IV are known compounds and are widely applied to the fields of chemical industry, food, medicine, materials, textile and the like. For example, dicarboxylic acids are often used to produce nylon materials, succinic acid is used in the synthesis of nylon x,4, glutaric acid is used to produce nylon 5,5 products, and adipic acid is used to produce nylon x,6 products. Azelaic acid is mainly used for producing dioctyl azelate plasticizer, and can also be used as raw material for producing spice, lubricating oil, oil agent and polyamide resin. It also has antibacterial effect, and can be used as food antiseptic. The gargle is beneficial to preventing and treating decayed teeth when used in gargle products, and can avoid cracking on the surface of soap when used in perfumed soap. Has good permeability to skin, and can be used in cream cosmetic to improve skin absorption function. Has multiple drug effects, and can be used in plaster for treating dermatosis. Has skin brightening and whitening effects. Azelaic acid or its zinc salt and vitamin B6 are used in hair care products, and are suitable for treating male hormone alopecia with vigorous endocrine, and stimulating hair growth. However, the use of such dicarboxylic acid compounds for controlling plant diseases such as rice blast, anthracnose, downy mildew, phytophthora root rot, gray mold and the like has not been reported.
The diseases caused by filamentous eukaryotic pathogens of plants account for about 70-80% of plant diseases. Diseases caused by several or even dozens of pathogens can be found on one crop. The filamentous eukaryotic pathogens comprise oomycetes, such as rice seedling rot caused by phytophthora, seedling damping-off and melon and fruit rot caused by pythium, tobacco black shank and potato late blight caused by phytophthora, and downy mildew caused by downy mildew; the filamentous eukaryotic pathogens also include fungi, especially diseases caused by Ascomycota, such as powdery mildew caused by powdery mildew, bakanae disease caused by Ascomycota, bakanae disease caused by wheat scab, and scab of apple and pear caused by Venturia nigrescens; rust disease caused by rust in Basidiomycota, smut disease caused by smut, rice blast, rice flax spot, corn big spot, small spot and the like caused by fungi imperfecti. Common symptoms include downy mildew, powdery mildew, white rust, black powder, rust powder, tobacco mold, black nevus, mildew, mushroom, cotton floc, granule, rope, clay grain, small black spot, etc.
The diseases are mainly spread in the field through air flow and water flow; in addition, insects can also transmit fungal and oomycete diseases. These diseases are extremely harmful to the production of grains, fruits, vegetables and the like. For example, Pyricularia oryzae caused rice blast is the most serious destructive disease of rice, and can cause great yield reduction, 40-50% in serious cases, and even no grain harvest. The rice blast not only occurs all over the world, but also occurs in various growth periods of rice, and can cause yield reduction to different degrees after the occurrence, particularly panicle neck blast can cause white ears to cause dead birth. The blast disease may occur in any growth period in any year in the province, and thus the damage of agricultural production thereof is extremely serious. For a long time, the rice blast causes more than 30 hundred million kilograms of grain loss to China every year, and even threatens the global grain safety. Another important fungal disease on plants, anthrax, is caused by anthrax bacteria. Pathogenic bacteria are spread by wind, rain and water droplet splashing; the wound facilitates invasion. High temperature and high humidity, heavy rain, improper fertilizer and water, improper management in transportation, poor plant growth and the like are all beneficial to the occurrence of diseases. Various crops, fruit trees and vegetables such as hot peppers, tomatoes, cucumbers and apples can be infected by anthracnose, and the influence on agricultural production is huge.
In addition, downy mildew and phytophthora blight caused by oomycetes are also important diseases of many crops, for example, various downy mildew of melons and grapes, late blight of potatoes and tomatoes, and phytophthora capsici, which all cause great losses to agricultural production.
For plant diseases caused by filamentous eukaryotic pathogens, chemical agents are generally adopted for preventing and treating, and plant health is promoted and pathogens are reduced by improving cultivation management measures. Currently, common pesticides for chemical control include Bordeaux mixture, chlorothalonil, thiophanate-methyl, carbendazim, pyraclostrobin, prochloraz.
The prevention and control of the diseases are always key technical problems in agricultural production, and the continuous development of green chemical pesticides for the diseases has important significance. Many filamentous eukaryotic pathogens parasitizing plants are expanded at the top of spore germination tubes or old hyphae, and secrete sticky substances, so that the pathogens are firmly adhered to the surface of a host to perform invasion, namely, attachment cells. Whether the attachment cells are formed or not is directly related to whether the pathogenic bacteria can successfully invade host tissues or not, and is a key step for causing plant diseases by using pyricularia, anthrax and oomycetes. The occurrence of these diseases can be effectively alleviated and controlled if compounds or measures are available that effectively inhibit the formation of adherent cells. Therefore, the development of inhibitors of the formation of adherent cells (i.e., substances that effectively inhibit the formation of adherent cells and thereby control the occurrence of various plant diseases) is of great significance for the control of plant fungal and oomycete diseases.
Through the research on the dicarboxylic acid compounds shown in the formulas I, II, III or IV, the invention obtains a new application which is different from the prior dicarboxylic acid compound technology and can be used for inhibiting the formation of attachment cells and preventing and treating plant diseases.
Disclosure of Invention
One of the purposes of the invention is to provide a new application of dicarboxylic acid compounds, and provide a novel plant protective agent for preventing and treating rice blast, anthracnose, downy mildew, phytophthora root rot or gray mold and the like on various plants including grain crops (such as rice, wheat, sorghum and corn), melons and fruits (such as apple, persimmon tree, orange, mango, walnut, kiwi fruit, jujube tree, lychee, longan, loquat, pomegranate, grape, watermelon and dragon fruit) and vegetables (such as hot pepper, cucumber, eggplant, balsam pear, pepper and kidney bean).
The technical scheme of the invention is as follows: the use of dicarboxylic acid compounds selected from the group consisting of compounds of formulae I, II, III and IV, isomers, hydrates or salts thereof for controlling plant diseases,
wherein n is an integer of 0 to 100, i.e., the compound has 0 to 100 carbons; m is an integer of 1-50, namely the part of the compound is 1-50 olefinic bonds; x is an integer of 0 to 50, i.e., the compound has 0 to 50 carbons; r is alkyl, alkoxy, aryl, aryloxy, heteroaryl, heteroaryloxy, alkenyl, alkynyl, hydroxyl, amino, fluorine, chlorine, bromine, iodine, nitro, nitroso, carboxyl, acyl, cyano or glycosyl.
Preferably, in the formula I, both ends of the chain of the compound of the formula I simultaneously have carboxyl functional groups, and n is 0-30, namely the part of the compound can have 0-30 carbons; m is 1 to 16, i.e., the portion of the compound may have 1 to 16 olefinic bonds. The compounds of formula I include, but are not limited to, linear compounds, and also include branched isomers thereof, as well as cis-trans isomers and positional isomers of olefins.
More preferably, n of formula I is 6; m is 1, i.e. the compound of formula I is selected from the following compounds in formula V:
preferably, in the formula II, both ends of the chain of the compound of the formula II simultaneously have carboxyl functional groups, and n is 0-48, namely the part of the compound can be 0-48 carbons. The compound of formula II includes, but is not limited to, linear compounds, and also includes branched isomers thereof, as well as cis-trans isomers and positional isomers of olefins.
Preferably, in the formula III, both ends of the chain of the compound in the formula III simultaneously have carboxyl functional groups, and n is 0-30, namely the part of the compound can have 0-30 carbons; x is 0 to 30, i.e., the portion of the compound can have 0 to 30 carbons. The compound of formula III includes, but is not limited to, linear compounds, and also includes branched chain isomers and stereoisomers thereof.
Preferably, in the formula IV, both ends of the chain of the compound in the formula IV have carboxyl functional groups, and n is 0-10, namely the part of the compound can have 0-10 carbons; x is 0 to 10, i.e., the portion of the compound can have 0 to 10 carbons. The compound of formula IV includes, but is not limited to, straight chain compounds, and also includes branched chain isomers thereof as well as positional isomers on the benzene ring.
The invention also aims to provide a plant protective agent or a bactericide, which contains a dicarboxylic acid compound selected from formulas I, II, III or IV and optionally auxiliary materials.
Preferably, a novel plant protective agent is provided for preventing the rice blast, the anthracnose, the downy mildew, the phytophthora root rot and the gray mold of plants.
Still preferably, the disease is selected from rice blast, melon downy mildew, pepper anthracnose, tomato gray mold, potato late blight, and pepper phytophthora blight.
The novel application of the dicarboxylic acid compound provided by the invention has the following advantages:
1. the invention discovers that the existing dicarboxylic acid compound has the function of inhibiting the formation of fungus attachment cells for the first time. Many plant-parasitic pathogenic fungi and oomycetes are enlarged at the top of their germ tubes or hyphae, secrete stickies that help them adhere firmly to the surface of the host, invade the plant tissue, and form attachment cells. The formation of pathogenic bacteria attachment cells is directly related to the success of the pathogenic bacteria attachment cells in invading host tissues, and is the key to the attack of plant diseases such as rice blast, anthracnose, downy mildew, phytophthora root rot, gray mold and the like. The inhibitor for formation of adherent cells is a substance which effectively inhibits the formation of adherent cells and thus inhibits the occurrence of various plant fungal or oomycete diseases.
It has been found through studies that dicarboxylic acid compounds of formulae I, II, III and IV are effective in inhibiting fungal or oomycete attachment cell formation.
2. The invention discovers that the dicarboxylic acid compounds can effectively prevent germs from infecting plants by inhibiting the formation of attachment cells, can be used for preventing and treating plant diseases with huge harm, including rice blast, anthracnose, downy mildew, phytophthora root rot and gray mold, and provides a new choice of plant protection medicines.
3. The invention discovers that the specific dicarboxylic acid compounds with specific structures can effectively inhibit the formation of fungus attachment cells within the concentration of 10-100ppm, and the control effect on plant diseases such as rice blast, anthracnose, downy mildew, phytophthora root rot, gray mold and the like reaches more than 80%.
4. The dicarboxylic acid compound has definite control effect on the activity of inhibiting formation of attachment cells, particularly controlling rice blast, anthracnose, downy mildew, phytophthora root rot and gray mold, and also has the advantages of greenness, environmental protection, less residue and good safety.
5. Compared with the existing compounds for preventing and controlling rice blast, anthracnose, downy mildew, phytophthora root rot and gray mold, the dicarboxylic acid compound of the invention is a known and widely used compound, and has the advantages of easy acquisition of raw materials, mature synthesis process, full research of impurities and mature quality control, thereby having more convenience and easy acquisition.
Detailed Description
The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.
Description of the drawings: the proportions referred to in the present invention are weight ratios, and refer to the proportions of the free or anhydrous substance, excluding salt ions or crystal water.
The plant protective agent for inhibiting the activity of forming adhered cells described in the present invention may be referred to as an adhered cell formation inhibitor.
The dicarboxylic acid compounds (compounds having the formulae I, II, III, IV and V) related to the present invention are known compounds and can be obtained commercially or by literature methods. For example, specific dicarboxylic acid compounds tested according to the invention are shown in Table 1.
Table 1 part of the compounds of the formulae I, II, III, IV and V and the corresponding compound numbers and the corresponding CAS numbers
EXAMPLE 1 inhibition of Anthrax bacteria attachment cell formation by dicarboxylic acid Compounds
1. And (3) detecting pathogenic bacteria: the anthrax strain is 20 strains in total, which are respectively: grape anthracnose bacteria, sorghum anthracnose bacteria, oil tea anthracnose bacteria, apple anthracnose bacteria, pear anthracnose bacteria, strawberry anthracnose bacteria, pepper tip anthracnose bacteria, pepper colletotrichum gloeosporioides bacteria, deep-split rhizopus adonna (8270) anthracnose bacteria, deep-split rhizopus laevigatus (8069) anthracnose bacteria, beautiful millettia bacteria, yellow pear anthracnose bacteria, cucumber anthracnose bacteria, momordica grosvenori anthracnose bacteria, camellia sinensis (9053) anthracnose bacteria, camellia sinensis (9059) anthracnose bacteria, cherry anthracnose bacteria, cruciferous vegetable anthracnose bacteria, walnut anthracnose bacteria and corn anthracnose bacteria.
2. The test method comprises the following steps:
1) anthrax produces conidia in large quantities: inoculating the anthrax bacterial strain to be activated on a potato agarose culture medium PDA, and culturing in a constant-temperature illumination incubator at 28 ℃. And 3-5 days later, the bacterial colony growing on the surface of the culture dish. And (3) washing all hyphae on the surface of the culture medium with sterile water, washing, airing, and culturing at 28 ℃ for about 48 hours under illumination, so that conidia generated in large quantity can be seen on the surface of the PDA.
2) Preparing an anthrax spore suspension: washing off spores on spore production plate with sterile water, filtering with three layers of filter paper, counting with blood counting plate, adjusting concentration to 2 × 105spores/mL.
3) Target compounds are added into the spore suspension according to different concentration gradients to prepare target solutions with the concentrations of 100ppm, 70ppm, 50ppm and 30ppm, and the target solutions are sequentially spotted on a hydrophobic glass slide. Four spots were spotted on each slide and treated with dark moisture. At 12 hours after inoculation, conidiophore attachment cell formation rates were observed and counted microscopically.
4) Counting: counting three points on each hydrophobic slide, counting 50 conidia in the center of each point, counting the number of formed anchorage cells, averaging the three groups of data, counting the formation rate of the anchorage cells, and calculating IC50The value is obtained.
3. And (3) test results: the 10 compounds have inhibitory activity on 20 anthrax bacteria.
TABLE 2 determination of IC50 values for 20 anthrax bacteria by dicarboxylic acid Compounds
| Serial number | Compound (I) | Anthrax host | IC50(ppm) |
| 1 | D2 | Grape | 37 |
| 2 | D2 | Sorghum grain | —— |
| 3 | D2 | Oil tea | 46 |
| 4 | D2 | Strawberry | 47 |
| 5 | D2 | Pear (pear) | —— |
| 6 | D2 | Apple (Malus pumila) | —— |
| 7 | D2 | Capsicum tip | 5 |
| 8 | D2 | Pepper glue spore | 8 |
| 9 | D2 | Deep-split bamboo root-seven (8270) | —— |
| 10 | D2 | Deep-split bamboo root-seven (8069) | —— |
| 11 | D2 | Beautiful millettia root | —— |
| 12 | D2 | Huanghua pear | —— |
| 13 | D2 | Cucumber (Cucumis sativus) | —— |
| 14 | D2 | Momordica grosvenori | —— |
| 15 | D2 | Red mountainTea (9053) | —— |
| 16 | D2 | Camellia japonica (9059) | —— |
| 17 | D2 | Cherry | 35 |
| 18 | D2 | Cruciferae vegetable | 78 |
| 19 | D2 | Walnut (walnut) | 49 |
| 20 | D2 | Corn (corn) | 62 |
TABLE 3 determination of IC50 values of dicarboxylic acid Compounds for 20 anthrax bacteria
| Serial number | Compound (I) | Anthrax host | IC50(ppm) |
| 1 | D9 | Grape | 14 |
| 2 | D9 | Sorghum grain | —— |
| 3 | D9 | Oil tea | 70 |
| 4 | D9 | Strawberry | —— |
| 5 | D9 | Pear (pear) | —— |
| 6 | D9 | Apple (Malus pumila) | —— |
| 7 | D9 | Capsicum tip | 13 |
| 8 | D9 | Pepper glue spore | 3 |
| 9 | D9 | Deep-split bamboo root-seven (8270) | —— |
| 10 | D9 | Deep-split bamboo root-seven (8069) | —— |
| 11 | D9 | Beautiful millettia root | —— |
| 12 | D9 | Huanghua pear | —— |
| 13 | D9 | Cucumber (Cucumis sativus) | —— |
| 14 | D9 | Momordica grosvenori | —— |
| 15 | D9 | Camellia japonica (9053) | —— |
| 16 | D9 | Camellia japonica (9059) | —— |
| 17 | D9 | Cherry | 87 |
| 18 | D9 | Cruciferae vegetable | 86 |
| 19 | D9 | Walnut (walnut) | 64 |
| 20 | D9 | Corn (corn) | 79 |
TABLE 4 determination of IC50 values of dicarboxylic acid Compounds for 20 anthrax bacteria
TABLE 5 determination of IC50 values of dicarboxylic acid Compounds for 20 anthrax bacteria
| Serial number | Compound (I) | Anthrax host | IC50(ppm) |
| 1 | D68 | Grape | 48 |
| 2 | D68 | Sorghum grain | —— |
| 3 | D68 | Oil tea | 32 |
| 4 | D68 | Strawberry | 90 |
| 5 | D68 | Pear (pear) | 58 |
| 6 | D68 | Apple (Malus pumila) | —— |
| 7 | D68 | Capsicum tip | 7 |
| 8 | D68 | Pepper glue spore | 7 |
| 9 | D68 | Deep-split bamboo root-seven (8270) | —— |
| 10 | D68 | Deep-split bamboo root-seven (8069) | 60 |
| 11 | D68 | Beautiful millettia root | —— |
| 12 | D68 | Huanghua pear | —— |
| 13 | D68 | Cucumber (Cucumis sativus) | —— |
| 14 | D68 | Momordica grosvenori | —— |
| 15 | D68 | Camellia japonica (9053) | —— |
| 16 | D68 | Camellia japonica (9059) | 40 |
| 17 | D68 | Cherry | 60 |
| 18 | D68 | Cruciferae vegetable | 46 |
| 19 | D68 | Walnut (walnut) | 53 |
| 20 | D68 | Corn (corn) | 68 |
TABLE 6 determination of IC50 values of dicarboxylic acid Compounds for 20 anthrax bacteria
TABLE 7 determination of IC50 values of dicarboxylic acid Compounds for 20 anthrax bacteria
TABLE 8 determination of IC50 values for 20 anthrax bacteria by dicarboxylic acid Compounds
| Serial number | Compound (I) | Anthrax host | IC50(ppm) |
| 1 | D90 | Grape | 41 |
| 2 | D90 | Sorghum grain | —— |
| 3 | D90 | Oil tea | 35 |
| 4 | D90 | Strawberry | 85 |
| 5 | D90 | Pear (pear) | 67 |
| 6 | D90 | Apple (Malus pumila) | —— |
| 7 | D90 | Capsicum tip | 5 |
| 8 | D90 | Pepper glue spore | 19 |
| 9 | D90 | Deep-split bamboo root-seven (8270) | —— |
| 10 | D90 | Deep-split bamboo root-seven (8069) | 55 |
| 11 | D90 | Beautiful millettia root | —— |
| 12 | D90 | Huanghua pear | —— |
| 13 | D90 | Cucumber (Cucumis sativus) | —— |
| 14 | D90 | Momordica grosvenori | —— |
| 15 | D90 | Camellia japonica (9053) | —— |
| 16 | D90 | Camellia japonica (9059) | 50 |
| 17 | D90 | Cherry | 68 |
| 18 | D90 | Cruciferae vegetable | 45 |
| 19 | D90 | Walnut (walnut) | 61 |
| 20 | D90 | Corn (corn) | 58 |
TABLE 9 determination of IC50 values of dicarboxylic acid Compounds for 20 anthrax bacteria
Example 2 inhibition of formation of Magnaporthe grisea adherent cells by dicarboxylic acid Compounds
1. And (3) detecting pathogenic bacteria: magnaporthe oryzae (Magnaporthe oryzae) P131.
2. The test method comprises the following steps:
1) the rice blast fungus produces conidia in large quantities: inoculating the rice blast strain to be activated onto a tomato oat flat OTA, and culturing in a constant-temperature illumination incubator at 28 ℃. And 3-5 days later, the bacterial colony growing on the surface of the culture dish. The colonies on OTA were sufficiently disrupted, then evenly spread onto new tomato juice oat plates and cultured in a constant temperature light incubator at 28 ℃. When the new mycelia grow out of the surface of the culture medium, the mycelia are gently broken by a cotton swab, washed clean with water, and dried. The culture dish is covered by a single layer of gauze, and the culture is performed for about 48 hours under the illumination of 28 ℃, namely, conidia generated on the surface of the OTA in large quantity can be seen.
2) Preparing a rice blast fungus spore suspension: washing hypha and spore on spore-forming plate with sterile water, filtering with three layers of filter paper, counting with blood counting plate, and adjusting concentration to 2 × 105spores/mL.
3) Target compounds are added into the spore suspension according to different concentration gradients to prepare target solutions with the concentrations of 100ppm, 70ppm, 50ppm and 30ppm, and the target solutions are sequentially spotted on a hydrophobic glass slide. Four spots were spotted on each slide and treated with dark moisture. At 12 hours after inoculation, conidiophore attachment cell formation rates were observed and counted microscopically.
4) Counting: counting three points of each hydrophobic slide, counting 50 conidia at the center of each point, counting the number of formed anchorage cells, averaging the three groups of data, counting the formation rate of the anchorage cells, and calculating IC50The value is obtained.
3. And (3) test results: inhibition of blast fungus P131 attachment cell formation by 20 compounds
TABLE 10 inhibition of Pyricularia oryzae P131 desmoplasia by dicarboxylic acid compounds
EXAMPLE 3 inhibition of formation of cells adhering to rubber-tipped YN42 by dicarboxylic acid Compound
1. And (3) detecting pathogenic bacteria: colletotrichum gloeosporioides (Colletotrichum aculatum) YN 42.
2. The test method comprises the following steps:
1) anthrax produces conidia in large quantities: inoculating the anthrax bacterial strain to be activated on a potato agarose culture medium PDA, and culturing in a constant-temperature illumination incubator at 28 ℃. And 3-5 days later, the bacterial colony growing on the surface of the culture dish. And (3) washing all hyphae on the surface of the culture medium with sterile water, washing, airing, and culturing at 28 ℃ for about 48 hours under illumination, so that conidia generated in large quantity can be seen on the surface of the PDA.
2) Preparing an anthrax spore suspension: washing off spores on spore production plate with sterile water, filtering with three layers of filter paper, counting with blood counting plate, adjusting concentration to 2 × 105spores/mL.
3) Target compounds are added into the spore suspension according to different concentration gradients to prepare target solutions with the concentrations of 100ppm, 70ppm, 50ppm and 30ppm, and the target solutions are sequentially spotted on a hydrophobic glass slide. Four spots were spotted on each slide and treated with dark moisture. At 12 hours after inoculation, conidiophore attachment cell formation rates were observed and counted microscopically.
4) Counting: counting three points on each hydrophobic slide, counting 50 conidia in the center of each point, counting the number of formed anchorage cells, averaging the three groups of data, counting the formation rate of the anchorage cells, and calculating the IC50 value.
3. And (3) test results: inhibition of formation of rubber tip spore YN42 attachment cells by 20 compounds
TABLE 11 inhibition of formation of cells by dicarboxylic acid compounds adhering to rubber-tipped YN42
EXAMPLE 4 inhibition of mango anthrax r13 appressorium formation by dicarboxylic acid compounds
1. And (3) detecting pathogenic bacteria: mango anthracnose (Colletotrichum gloeosporioides) r13
2. The test method comprises the following steps:
1) anthrax produces conidia in large quantities: inoculating the anthrax bacterial strain to be activated on a potato agarose culture medium PDA, and culturing in a constant-temperature illumination incubator at 28 ℃. And 3-5 days later, the bacterial colony growing on the surface of the culture dish. And (3) washing all hyphae on the surface of the culture medium with sterile water, washing, airing, and culturing at 28 ℃ for about 48 hours under illumination, so that conidia generated in large quantity can be seen on the surface of the PDA.
2) Preparing an anthrax spore suspension: washing off spores on spore production plate with sterile water, filtering with three layers of filter paper, counting with blood counting plate, adjusting concentration to 2 × 105spores/mL.
3) Target compounds are added into the spore suspension according to different concentration gradients to prepare target solutions with the concentrations of 100ppm, 70ppm, 50ppm and 30ppm, and the target solutions are sequentially spotted on a hydrophobic glass slide. Four spots were spotted on each slide and treated with dark moisture. At 12 hours after inoculation, conidiophore attachment cell formation rates were observed and counted microscopically.
4) Counting: counting three points on each hydrophobic slide, counting 50 conidia in the center of each point, counting the number of formed anchorage cells, averaging the three groups of data, counting the formation rate of the anchorage cells, and calculating the IC50 value.
3. And (3) test results: inhibition of mango anthrax r13 attachment cell formation by 20 compounds
TABLE 12 inhibition of mango anthrax r13 attachment cell formation by dicarboxylic acid compounds
| Serial number | Compound (I) | Concentration (ppm) | Percentage of adherent cell formation (%) |
| 1 | D1 | 100 | 0 |
| 2 | D2 | 70 | 0 |
| 3 | D5 | 70 | 0 |
| 4 | D9 | 70 | 0 |
| 5 | D16 | 100 | 0 |
| 6 | D24 | 70 | 5 |
| 7 | D28 | 100 | 0 |
| 8 | D29 | 100 | 0 |
| 9 | D36 | 70 | 10 |
| 10 | D42 | 100 | 0 |
| 11 | D50 | 100 | 0 |
| 12 | D51 | 50 | 0 |
| 13 | D64 | 100 | 0 |
| 14 | D74 | 70 | 10 |
| 15 | D83 | 100 | 3 |
| 16 | D88 | 100 | 0 |
| 17 | D90 | 70 | 8 |
| 18 | D98 | 100 | 0 |
| 19 | D109 | 100 | 15 |
| 20 | D113 | 100 | 8 |
EXAMPLE 5 inhibition of Botrytis cinerea by dicarboxylic acid Compounds
1. And (3) detecting pathogenic bacteria: botrytis cinerea (Botrytis cinerea)
2. The test method comprises the following steps:
1) activation of Botrytis cinerea: taking a PDA culture medium, pouring the PDA culture medium into a flat plate in a super clean workbench, picking a small amount of botrytis cinerea strains by using inoculating rings after the culture medium is cooled and solidified, respectively putting the small amount of botrytis cinerea strains into each culture dish, putting the culture dishes into an incubator at 28 ℃, carrying out inverted culture, wherein the first activation time is one week, and carrying out secondary activation according to the method after hyphae of the botrytis cinerea strains become grey green and grow over the flat plate.
2) Preparation of a botrytis cinerea spore suspension: culturing the activated botrytis cinerea for 7 days (28 ℃) until the thallus produces spores. Washing the thallus with sterile water for several times to obtain spore suspension, counting the spore suspension with a blood counting chamber, and diluting the spore suspension to 1 × 104spores/mL for use.
3) 5 target compounds were formulated one day in advance into a liquid medicine with a final concentration of 100ppm (control pesticide: prochloraz), uniformly spraying the prochloraz on tomato leaves, preserving moisture, standing, drying the leaves after 24 hours until no water drops exist on the surfaces, preparing a spore suspension, and dotting the spore suspension on the tomato leaves, wherein each leaf is dotted with 2 drops of the spore suspension, and each drop of the spore suspension is 20 mu L. The culture was incubated at 20 ℃ for 3 days with moisture retention, and the disease was observed. Inoculating 20 μ L of Botrytis cinerea B05.10 spore liquid (1 × 10)4spores/mL), tomato leaf development after 72 hours (20 ℃), spore liquid containing 1/10 PDB.
3. And (3) test results:
the test result shows that: the compounds D9, D51 and D68 with the concentration of 100ppm have good disease prevention effect, wherein the compounds D51 and D68 with the concentration of 100ppm have no disease at all. The control pesticide (prochloraz) also did not develop disease.
TABLE 13 control of tomato gray mold by dicarboxylic acid compounds
| Serial number | Compound (I) | Concentration (ppm) | Control effect (%) |
| 1 | D2 | 10 | 10.10 |
| 2 | D2 | 100 | 40.32 |
| 3 | D9 | 10 | 20.04 |
| 4 | D9 | 100 | 60.41 |
| 5 | D29 | 10 | 3.62 |
| 6 | D29 | 100 | 20.30 |
| 7 | D51 | 10 | 78.33 |
| 8 | D51 | 100 | 100.04 |
| 9 | D68 | 10 | 60.82 |
| 10 | D68 | 100 | 96.44 |
EXAMPLE 6 prevention of Anthrax disease in Arabidopsis thaliana by dicarboxylic acid Compounds
1. And (3) detecting pathogenic bacteria: arabidopsis thaliana anthracnose bacteria (Colletotrichum gloeosporioides)
2. The test method comprises the following steps:
1) anthrax produces conidia in large quantities: inoculating the anthrax bacterial strain to be activated on a potato agarose culture medium PDA, and culturing in a constant-temperature illumination incubator at 28 ℃. And 3-5 days later, the bacterial colony growing on the surface of the culture dish. And (3) washing all hyphae on the surface of the culture medium with sterile water, washing, airing, and culturing at 28 ℃ for about 48 hours under illumination, so that conidia generated in large quantity can be seen on the surface of the PDA.
2) Preparing an anthrax spore suspension: washing off spores on spore production plate with sterile water, filtering with three layers of filter paper, counting with blood counting plate, adjusting concentration to 2 × 105spores/mL.
3) Adding the target compound into the spore suspension according to different concentration gradients to prepare target solutions with the concentrations of 100ppm and 50ppm, spraying the target solutions onto arabidopsis thaliana leaves, counting the morbidity after seven days, and calculating the control effect (%).
3. And (3) test results: the specific results are shown in Table 14.
TABLE 14 control of Arabidopsis thaliana anthracnose by dicarboxylic acid compounds
| Serial number | Compound (I) | Concentration (ppm) | Control effect (%) |
| 1 | D2 | 50 | 9.61 |
| 2 | D2 | 100 | 44.42 |
| 3 | D9 | 50 | 10.70 |
| 4 | D9 | 100 | 30.51 |
| 5 | D29 | 50 | 24.63 |
| 6 | D29 | 100 | 56.84 |
| 7 | D51 | 50 | 63.40 |
| 8 | D51 | 100 | 98.71 |
| 9 | D68 | 50 | 10.70 |
| 10 | D68 | 100 | 38.73 |
Example 7 prevention of Potato late blight by dicarboxylic acid Compound
1. And (3) detecting pathogenic bacteria: potato late blight bacterium (Phytophthora infestans)
2. The test method comprises the following steps:
potato variety: "Xisen No. 6" is a high-susceptibility late blight cultivar.
Preparation of a spore suspension of Phytophthora infestans
Phytophthora infestans strain MZ15-30 was inoculated into rye medium for a total of 10 plates (90mm diameter) and cultured until day 13 to examine whether contamination occurred. The plates were kept free of contamination, 10mL of sterile distilled water was added to each plate on a sterile bench, and the plates were incubated in a freezer at 4 ℃ for 3-4h to allow the sporangia to rupture and release zoospores.
Zoospores were carefully transferred to 50mL centrifuge tubes and 4 plates were transferred to one centrifuge tube. Centrifuge at 2500rpm for 10 minutes at low speed and carefully pour out the supernatant, leave 200uL of liquid at the bottom of the tube and resuspend the pellet in 2mL sterile distilled water. mu.L of the resuspended zoospores were diluted 1:10 with sterile distilled water and counted under a biomicroscope using a Modified Fuchs Rosensanal Counting Chamber (depth 0.2 mm; Weber Scientific International, Teddington, UK). The diluted zoospores were mixed well with a pipette and loaded on both sides of a hemocytometer. The total number of zoospores in 16 squares of the haemocytometer was counted and then divided by 4 to calculate the average number of zoospores per square. Multiplying this number by 10,000, the total zoospore concentration per ml was calculated. The spore concentration used for inoculation was diluted to 15,000 per ml with sterile distilled water.
Inoculating the test plants in vivo by adding the target compound to the spore suspension of P.infestans
1) Preparing 100ppm of liquid medicine, uniformly spraying the liquid medicine on 20-day-old potato leaves, performing moisture preservation culture in an artificial climate chamber, after 24 hours, uniformly spraying the prepared liquid medicine on the potato leaves, performing moisture preservation culture in the artificial climate chamber (20 ℃, 18 hours of light and 6 hours of darkness), and counting the disease index after 4-5 days. As the strain used in the experiment is a medium-strong pathogenic strain, statistics is started after 4 days of inoculation, and disease indexes and control effects are continuously counted for three days and recorded by photographing.
2) Spray-on compounds
Name: d2, D9, D29, D68 and D51
Concentration 100ppm (μ g/mL)
Medicament solvent: DMSO at a concentration of 1 ‰
3) Late blight of spraying
Spraying late blight bacteria strain:
the strain number is as follows: MZ
Physiological races: r1.R3.R4.R7.R9.R10.R11
The characteristics of the strain are as follows: the medium-strength strain has strong toxicity and quick onset.
Spore concentration: 250 zoospores/10 μ L
3. And (3) test results: the 5 compounds have certain control effect on potato late blight. The D9, D29, D51 and D68 have obvious control effect, the control effect reaches more than 85 percent, and the effect of the D2 compound is slightly worse than that of the other four compounds.
TABLE 15 control of potato late blight by dicarboxylic acid compounds
| Serial number | Compound (I) | Concentration (ppm) | Control effect (%) |
| 1 | D2 | 50 | 0.00 |
| 2 | D2 | 100 | 31.53 |
| 3 | D9 | 50 | 71.34 |
| 4 | D9 | 100 | 93.20 |
| 5 | D29 | 50 | 60.54 |
| 6 | D29 | 100 | 90.65 |
| 7 | D51 | 50 | 67.48 |
| 8 | D51 | 100 | 95.66 |
| 9 | D68 | 50 | 56.40 |
| 10 | D68 | 100 | 88.04 |
EXAMPLE 84 field trials of dicarboxylic acid Compounds for controlling Benincasa downy mildew (white Lotus Royvale)
1. Test conditions
1.1 test materials
And (3) test crops: white gourd
The control object is: downy mildew of white gourd
Test site: bailianluoyiwu (a Chinese character of' Bailian Luoyiwu
1.2 test Agents
Control agents:
yinfeili (687.5g/L fluopicolide propamocarb) -Bayer
1.3 design of the experiment
TABLE 16 test agent concentration design
| Serial number | Medicament | Dilution factor |
| 1 | 15％D2 | 1000 times of |
| 2 | 15％D29 | 1000 times of |
| 3 | 15％D9 | 1000 times of |
| 4 | 15％D51 | 1000 times of |
| 5 | Silver Fali (687.5g/L Fluopicolide-propamocarb) | 1000 times of |
| 6 | CK | 0 |
1.4 application time and methods
The application time is 2 times in total, and the date is 4 and 5 days in 2019 and 4 and 12 days in 2019. The wax gourd applied for the first time has good growth condition, the wax gourd belongs to the middle stage of hanging the wax gourd, the soil humidity is suitable for the growth of crops, other diseases are less, downy mildew occurs before the test, and the wax gourd belongs to the middle stage of the downy mildew.
2. Investigation, recording and measuring method
2.1 Meteorological and soil data
2.1.1 Meteorological data survey
| Date | Maximum air temperature | Lowest air temperature | Weather (weather) | Wind direction and force | Air quality index |
| 019-04-05 Friday | 31℃ | 22℃ | Light rain | Dongfeng 2 grade | 28 excellent |
| 2019-04-06 Saturday | 31℃ | 22℃ | Thunderstorm rain-cloudy | Southeast wind 2 level | 26 you (Chinese character of 'Yuan') |
| 2019-04-07 Sunday | 34℃ | 22℃ | Cloudy-sunny | Northwest wind 2 grade | 31 you |
| 2019-04-08 Monday | 34℃ | 23℃ | Cloudy-sunny | Southeast wind 2 level | 32 excellent |
| 2019-04-09 Tuesday | 36℃ | 23℃ | All-weather | Southeast wind 2 level | 35 excellent |
| 2019-04-10 Wednesday | 38℃ | 24℃ | All-weather | Southeast wind 2 level | 39 you |
| 2019-04-11 Thursday | 37℃ | 24℃ | All-weather | Southeast wind 2 level | 37 you |
| 2019-04-12 Friday | 35℃ | 24℃ | Thunderstorm rain-fine | 3-grade southeast wind | 34 you (Chinese character of 'mu' an |
2.1.2 soil data
The soil has sufficient water content, and is beneficial to the growth of plants.
2.1.3 methods of investigation:
as wax gourd downy mildew occurs before the test, the test belongs to a therapeutic test, each treatment area is 20 square meters, two plants are investigated at each point by adopting a random 5-point investigation method, the leaves of the upper half part of each plant are investigated, the area size of downy mildew spots is counted, and the disease condition index of each treatment plant is investigated and counted by adopting a national standard grading method.
2.1.4 investigation time and number of surveys
The control effect was investigated 7 days after the first dose and 7 days after the second dose, respectively.
2.1.5 method for calculating drug effect
Grading standard of leaf disease conditions:
level 0: no scab
Level 1: the lesion area accounts for less than 5% of the whole leaf area;
and 3, level: the area of the lesion spots accounts for less than 6-10% of the area of the whole leaf;
and 5, stage: the lesion area accounts for less than 11-20% of the whole leaf area;
and 7, stage: the area of the lesion spots accounts for less than 21-50% of the area of the whole leaf;
and 9, stage: the lesion area accounts for more than 51 percent of the whole leaf area;
3 results and analysis
3.1 test results
TABLE 17 field test results for wax gourd downy mildew
| Drug treatment | Dilution factor | Number of pre-drug base | Index of disease condition | Prevention effect/%) |
| D2 | 1000 times of | 15.39 | 13.35 | 54.22 |
| D29 | 1000 times of | 13.82 | 10.33 | 60.55 |
| D9 | 1000 times of | 10.10 | 7.71 | 59.71 |
| D51 | 1000 times of | 9.23 | 7.14 | 63.28 |
| Yinfeili (silver Fanli) | 1000 times of | 15.58 | 11.24 | 61.92 |
| CK | 0 | 13.39 | 28.21 | 0 |
The test result shows that: as can be seen from the whole test process, the index of the pre-drug disease of wax gourd belongs to a higher level, which indicates that the disease is in the middle and later stages, and the control effects of 1000 times of the D2, D29, D9 and D51 samples are respectively found by 7 days after the first application: 54.22-60.55-59.71-63.28%, and the control effect of the contrast medicament silver Famili is 61.92% in 1000 times; the prevention and treatment effect of D51 is higher than that of a control medicament, the prevention and treatment effect can reach 63.28%, and the prevention and treatment effects of D29 and D9 on wax gourd downy mildew are equivalent to that of the control medicament silver farad; the D2 medicament has low control effect, only 54.22 percent, can effectively control the scab of the infected white gourd leaves in one pesticide application experiment, and continuously expands the downy mildew of a control blank group.
EXAMPLE 94 field test report of dicarboxylic acid Compounds for controlling pumpkin anthracnose (white Lotus Royuncun)
1. Test conditions
1.1 test materials
And (3) test crops: pumpkin (pumpkin)
The control object is: anthracnose of pumpkin
Test site: bailianluoyiwu (a Chinese character of' Bailian Luoyiwu
1.2 test Agents
Control agents:
naldipingol (25% trifloxystrobin 50% tebuconazole) -Bayer
Zhengjia (20% difenoconazole) -Hainan Zhengchang nonggaokou Co., Ltd
1.3 design of the experiment
TABLE 18 test agent concentration design
| Serial number | Medicament | Dilution factor |
| 1 | 15％D2 | 1000 times of |
| 2 | 15％D29 | 1000 times of |
| 3 | 15％D9 | 1000 times of |
| 4 | 15％D51 | 1000 times of |
| 5 | Naidiping stable (25% trifloxystrobin, 50% tebuconazole) | 2000 times of |
| 6 | Zhengjia (20% difenoconazole) | 750 times of |
| 7 | CK | 0 |
1.4 application time and methods
The application time is 2 times in total, and the date is 3 and 4 days in 2019 and 3 and 11 days in 2019. The pumpkin applied for the first time has good growth condition, the soil humidity is suitable for the growth of crops, other diseases are less, and anthracnose occurs before the test, which belongs to the middle stage of anthracnose occurrence.
2. Investigation, recording and measuring method
2.1 Meteorological and soil data
2.1.1 Meteorological data survey
2.1.2 soil data
The soil has sufficient water content, and is beneficial to the growth of plants.
2.1.3 methods of investigation:
the pumpkin anthracnose occurs before the test, belongs to a therapeutic test, each treatment area is 20 square meters, two plants are investigated at each point by adopting a random 5-point investigation method, all leaves are investigated at each plant, the area of the anthracnose spot is counted, and the disease index of each treatment plant is investigated and counted by adopting a national standard classification method.
2.1.4 investigation time and number of surveys
The control effect was investigated 10 days after the first dose and 7 days after the second dose, respectively.
2.1.5 method for calculating drug effect
Grading standard of leaf disease conditions:
level 0: no scab
Level 1: the lesion area accounts for less than 5% of the whole leaf area;
and 3, level: the area of the lesion spots accounts for less than 6-10% of the area of the whole leaf;
and 5, stage: the lesion area accounts for less than 11-20% of the whole leaf area;
and 7, stage: the area of the lesion spots accounts for less than 21-50% of the area of the whole leaf;
and 9, stage: the lesion area accounts for more than 51 percent of the whole leaf area;
3 results and analysis
3.1 test results
TABLE 19 field test results for pumpkin anthracnose
The test result shows that: as can be seen from the whole test process, the pre-drug disease index of the pumpkin belongs to a higher level, which indicates that the disease is in a middle stage, and the prevention effects of 1000 times of the D2, D29, D9 and D51 samples are respectively found by 7 days after the first drug application: 50.33% -43.71% -59.82% -55.30%, the control medicament Naidikang is 49.44% in 2000 times of prevention and treatment effect, and the best 750 times of prevention and treatment effect is 46.91%; the prevention and treatment effects of D9 and D51 are higher than those of a control medicament, the prevention and treatment effect of D9 diluted by 1000 times is the best, and is up to 59.82%, and the prevention and treatment effect of D51 diluted by 1000 times is the second, and can reach 55.30%; and D29 is lower than the control drug, Naidi, stable and good, by as low as 43.71%. Over time, the control effect is improved to different degrees in 10 days after the second application, the control effect is up to 62.61% at the highest D9 time, and the control effect is up to 58.80% at the second D51 time, which is slightly higher than 75% of the control agent 2000 times in molesta (58.80%), and the control effect of D2 is up to 57.73%, which is equivalent to 2000 times in molesta and 750 times in good condition of the control agent 2000 times. The prevention effect of D29 is only 50.80%, which is 750 times less than 2000 times of Nadichai stability and good effect of the contrast agent.
EXAMPLE 104 test for controlling downy mildew of melon with dicarboxylic acid Compound
1. Test conditions
1.1 test materials
And (3) test crops: melon (sweet melon)
The control object is: downy mildew of melon
Test site: the well-defined region of Beijing City
1.2 test Agents
Test agents of 100ppm of D2, D29, D9 and D51.
Control agents: azoxystrobin (25%)
1.3 design of the experiment
TABLE 20 test agent concentration design
1.4 cell arrangements
The test, control and blank cells were randomized block wise.
Cell area: 10-12m2
The number of repetitions: 4 times (twice)
The dosage is as follows: each dose was repeated 4 times for a total of 10L water to a final concentration of 100 ppm.
2 investigating, recording and measuring method
2.1 investigation method:
before the test, the muskmelon downy mildew occurs, a 10-point random sampling method is adopted, ten muskmelon seedlings are taken at each ridge at random, all the leaves are investigated, and the grading is carried out according to the percentage of the lesion area on each leaf to the whole leaf area.
2.2 investigation time and number of surveys
The control effect was investigated 8 days after the first dose and 8 days after the second dose, respectively.
2.3 method of calculating drug efficacy
Grading standard of leaf disease conditions:
level 0: no scab
Level 1: the lesion area accounts for less than 5% of the whole leaf area;
and 3, level: the area of the lesion spots accounts for less than 6-10% of the area of the whole leaf;
and 5, stage: the lesion area accounts for less than 11-20% of the whole leaf area;
and 7, stage: the area of the lesion spots accounts for less than 21-50% of the area of the whole leaf;
and 9, stage: the lesion area accounts for more than 51 percent of the whole leaf area;
3 results and analysis
TABLE 21 field test results for melon downy mildew
| Drug treatment | Dilution factor | Number of pre-drug base | Index of disease condition | Prevention effect/%) |
| D2 | 1000 times of | 2.20 | 6.83 | 22.45 |
| D29 | 1000 times of | 4.11 | 5.55 | 75.88 |
| D9 | 1000 times of | 2.58 | 6.96 | 26.63 |
| D51 | 1000 times of | 0.67 | 4.58 | 34.51 |
| Azoxystrobin | 2500 times of | 1.35 | 4.36 | 49.58 |
| CK | 0 | 2.88 | 8.85 | 0 |
The test result shows that: as can be seen from the whole test process, the index of the pre-drug disease of the melon belongs to a lower level, which indicates that the disease is in the early stage, and the control effects of 1000 times of the D2, D29, D9 and D51 samples are respectively found by 7 days after the first application: 22.45% -75.88% -26.63% -34.51%, and the control effect of the azoxystrobin is 49.58% compared with 2500 times; the control effect of D29 is higher than that of a control medicament, the control effect can reach 75.88%, and the control effect of D51 on melon downy mildew is lower than that of the control medicament azoxystrobin; the control effect of the D2 and D9 medicaments is low, only 22.45 percent and 26.63 percent, the disease spots of the susceptible melon leaves can be effectively controlled in one application experiment, and the downy mildew of a control blank group is continuously expanded.
EXAMPLE 114 field test report for control of cowpea anthracnose with samples
1. Test conditions
1.1 test materials
And (3) test crops: cowpea
The control object is: anthracnose of cowpea
Test site: mountain slope village
1.2 test Agents
Control agents:
naldipingol (25% trifloxystrobin 50% tebuconazole) -Bayer
Zhengjia (20% difenoconazole) -Hainan Zhengchang nonggaokou Co., Ltd
1.3 design of the experiment
TABLE 22 test agent concentration design
| Serial number | Medicament | Dilution factor |
| 1 | 15％D2 | 1000 times of |
| 2 | 15％D29 | 1000 times of |
| 3 | 15％D9 | 1000 times of |
| 4 | 15％D51 | 1000 times of |
| 5 | Naidiping stable (25% trifloxystrobin, 50% tebuconazole) | 2000 times of |
| 6 | Zhengjia (20% difenoconazole) | 750 times of |
| 7 | CK | 0 |
1.4 application time and methods
The application time is 2 times in total during the test period, and the date is 3 and 13 days in 2019 and 3 and 20 days in 2019. The cowpea applied for the first time has good growth condition, the soil humidity is suitable for the growth of crops, other diseases are less, and anthracnose occurs before the test, and belongs to the middle and later stages of anthracnose occurrence.
2. Investigation, recording and measuring method
2.1 Meteorological and soil data
2.1.1 Meteorological data survey
2.1.2 soil data
The soil has sufficient water content, and is beneficial to the growth of plants.
2.1.3 methods of investigation:
according to the method, cowpea anthracnose occurs before a test, the cowpea anthracnose belongs to a therapeutic test, each treatment area is 50 square meters, a random 5-point investigation method is adopted, two plants are investigated at each point, cowpea leaves are investigated at each plant, the area of anthracnose scabs on fruits is counted, and the disease index of each treatment plant is investigated and counted by a national standard grading method.
2.1.4 investigation time and number of surveys
The control effect was investigated 7 days after the first dose and 7 days after the second dose, respectively.
2.1.5 method for calculating drug effect
Grading standard of leaf disease conditions:
level 0: no scab
Level 1: the lesion area accounts for less than 5% of the whole leaf area;
and 3, level: the area of the lesion spots accounts for less than 6-10% of the area of the whole leaf;
and 5, stage: the lesion area accounts for less than 11-20% of the whole leaf area;
and 7, stage: the area of the lesion spots accounts for less than 21-50% of the area of the whole leaf;
and 9, stage: the lesion area accounts for more than 51 percent of the whole leaf area;
3 results and analysis
3.1 test results
TABLE 23 field test results for cowpea anthracnose
The test result shows that: as can be seen from the whole test process, the index of the disease before the medicine of the cowpea belongs to a higher level, which indicates that the disease is in the middle and later stages, and the control effects of 1000 times of the D2, D29, D9 and D51 samples are respectively found by 7 days after the first medicine application: 48.21% -55.33% -42.80% -44.61%, the control medicament Naidiping has a control effect of 46.82% 2000 times and a good control effect of 36.64% 750 times. Over time, the control effect of the compound pesticide is improved in different degrees in 7 days after the second pesticide application, the control effect of 4 samples on the anthracnose of cowpea can reach more than 50%, the control effect of the D29 sample can reach 61.50% at most, the control effect of the D2 and D51 samples can reach about 57%, the control effect of the D9 sample is slightly lower, and the control effect is only 51% between stable control and good control.
EXAMPLE 124 field trials of dicarboxylic acid Compounds for controlling Pepper anthracnose
1. Test conditions
1.1 test materials
And (3) test crops: chili pepper
The control object is: anthracnose of hot pepper
Test site: bailianluoyiwu (a Chinese character of' Bailian Luoyiwu
1.2 test Agents
Control agents:
naldipingol (25% trifloxystrobin 50% tebuconazole) -Bayer
1.3 design of the experiment
TABLE 24 test agent concentration design
1.4 application time and methods
The application time is 2 times in total during the test period, and the date is 2 months and 13 days in 2019 and 2 months and 20 days in 2019. The growth condition of the pepper applied for the first time is good, the soil humidity is suitable for the growth of crops, other diseases are few, and anthracnose occurs before the test, and belongs to the middle stage of the anthracnose.
2. Investigation, recording and measuring method
2.1 Meteorological and soil data
2.1.1 Meteorological data survey
| Date | Maximum air temperature | Lowest air temperature | Weather (weather) | Wind direction and force | Air quality index |
| 2019-02-13 Wednesday | 30℃ | 20℃ | Clear to cloudy | 3-grade southeast wind | 26 you (Chinese character of 'Yuan') |
| 2019-02-14 Thursday | 30℃ | 20℃ | Cloudy | 3-grade southeast wind | 26 you (Chinese character of 'Yuan') |
| 2019-02-15 Friday | 30℃ | 20℃ | Cloudy | 3-grade southeast wind | 24 excellent |
| 2019-02-16 Saturday | 31℃ | 20℃ | Cloudy | 3-grade southeast wind | 23 Excellent |
| 2019-02-17 Sunday | 30℃ | 21℃ | Cloudy-rainy | 4-grade southeast wind | 20 excellent |
| 2019-02-18 Monday | 30℃ | 21℃ | Light rain | 3-grade southeast wind | 23 Excellent |
| 2019-02-19 Tuesday | 32℃ | 21℃ | Cloudy | Southeast wind 2 level | 25 excellence |
| 2019-02-20 Wednesday | 35℃ | 21℃ | Thunderstorm rain-cloudy | 3-grade southeast wind | 24 excellent |
| 2019-02-21 Thursday | 35℃ | 20℃ | Thunderstorm rain | Southeast wind 2 level | 23 Excellent |
| 2019-02-22 Friday | 31℃ | 21℃ | Cloudy | Southeast wind 2 level | 38 you (Chinese character of 'mu' an |
| 2019-02-23 Saturday | 29℃ | 18℃ | Cloudy | Southeast wind 2 level | 31 you |
| 2019-02-24 Sunday | 24℃ | 17℃ | Light rain | Northeast wind 3 grade | 19 you |
| 2019-02-25 Monday | 27℃ | 21℃ | Cloudy | Dongfeng 3 grade | 38 you (Chinese character of 'mu' an |
| 2019-02-26 Tuesday | 27℃ | 20℃ | Little rain to cloudy | 3-grade southeast wind | 38 you (Chinese character of 'mu' an |
| 2019-02-27 Wednesday | 31℃ | 20℃ | Cloudy | 3-grade southeast wind | 33 you |
2.1.2 soil data
The soil has sufficient water content, and is beneficial to the growth of plants.
2.1.3 methods of investigation:
because pepper anthracnose occurs before the test, the test belongs to a therapeutic test, each treatment area is 20 square meters, two plants are investigated at each point by adopting a random 5-point investigation method, all leaves are investigated at each plant, the area of the anthracnose spot is counted, and the disease index of each treatment plant is investigated and counted by adopting a national standard classification method.
2.1.4 investigation time and number of surveys
The control effect was investigated 7 days after the first dose and 7 days after the second dose, respectively.
2.1.5 method for calculating drug effect
Grading standard of leaf disease conditions:
level 0: no scab
Level 1: the lesion area accounts for less than 5% of the whole leaf area;
and 3, level: the area of the lesion spots accounts for less than 6-10% of the area of the whole leaf;
and 5, stage: the lesion area accounts for less than 11-20% of the whole leaf area;
and 7, stage: the area of the lesion spots accounts for less than 21-50% of the area of the whole leaf;
and 9, stage: the lesion area accounts for more than 51 percent of the whole leaf area;
3 results and analysis
3.1 test results
TABLE 25 field test results for pepper anthracnose
The test result shows that: as can be seen from the whole test process, the index of the disease of the pepper before the drug is in a higher level, which indicates that the disease is in a middle stage, and the control effects of 1000 times of the D2, D29, D9 and D51 samples are respectively found by 7 days after the first drug application: 50.13% -37.20% -62.11% -50.34%, the control effect of 2000 times of Naidi of the contrast medicament is 49.50%, the control effects of D2, D9 and D51 are all higher than those of the contrast medicament, the control effect of D91000 times is the best, and is 62.11%, and the control effect of D51 diluted 1000 times can reach 50.34%; the control effect of D2 is 50.13% which is equal to 2000 times of Nadichai of contrast agent, and the control effect of D29 is the lowest, as low as 37.20%. Over time, the control effect is improved to different degrees in 7 days after the second application, the highest control effect is 1000 times of D9, the control effect reaches 82.11%, 75% of Naidiping stability (58.10%) obviously higher than 2000 times of that of a contrast medicament is obviously achieved, the control effect of D2 reaches 74.93%, the control effect of D29 is 54.64%, and the control effect of Naidiping stability is lower than 2000 times of that of the contrast medicament.
EXAMPLE 134 field test of dicarboxylic acid Compounds for controlling anthracnose of Pepper fruits
1. Test conditions
1.1 test materials
And (3) test crops: chili pepper
The control object is: anthracnose of hot pepper
Test site: mountain slope village
1.2 test Agents
Control agents:
naldipingol (25% trifloxystrobin 50% tebuconazole) -Bayer
Zhengjia (20% difenoconazole) -Hainan Zhengchang nonggaokou Co., Ltd
1.3 design of the experiment
TABLE 26 test agent concentration design
| Serial number | Medicament | Dilution factor |
| 1 | 15％D2 | 1000 times of |
| 2 | 15％D29 | 1000 times of |
| 3 | 15％D9 | 1000 times of |
| 4 | 15％D51 | 1000 times of |
| 5 | Naidiping stable (25% trifloxystrobin, 50% tebuconazole) | 2000 times of |
| 6 | Zhengjia (20% difenoconazole) | 750 times of |
| 7 | CK | 0 |
1.4 application time and methods
The application time is 2 times in total during the test period, and the date is 3 and 11 days in 2019 and 3 and 18 days in 2019. The growth condition of the pepper applied for the first time is good, the soil humidity is suitable for the growth of crops, other diseases are few, and anthracnose occurs before the test, and belongs to the middle and later stages of anthracnose occurrence.
2. Investigation, recording and measuring method
2.1 Meteorological and soil data
2.1.1 Meteorological data survey
2.1.2 soil data
The soil has sufficient water content, and is beneficial to the growth of plants.
2.1.3 methods of investigation:
because pepper anthracnose occurs before the test, the test belongs to a therapeutic test, each treatment area is 50 square meters, two plants are investigated at each point by adopting a random 5-point investigation method, the number of the whole pepper fruit is investigated at each plant, the area of the anthracnose disease spot on the fruit is counted, and the disease index of each treatment plant is investigated and counted by adopting a national standard grading method.
2.1.4 investigation time and number of surveys
The control effect was investigated 7 days after the first dose and 7 days after the second dose, respectively.
2.1.5 method for calculating drug effect
Grading standard of leaf disease conditions:
level 0: no scab
Level 1: the lesion area accounts for less than 5% of the whole leaf area;
and 3, level: the area of the lesion spots accounts for less than 6-10% of the area of the whole leaf;
and 5, stage: the lesion area accounts for less than 11-20% of the whole leaf area;
and 7, stage: the area of the lesion spots accounts for less than 21-50% of the area of the whole leaf;
and 9, stage: the lesion area accounts for more than 51 percent of the whole leaf area;
2 results and analysis
2.1 test results
TABLE 27 field test results for anthracnose of capsicum fruits
The test result shows that: as can be seen from the whole test process, the index of the disease of the pepper before the drug is in a higher level, which indicates that the disease is in the middle and later stages, and the control effects of 1000 times of the D2, D29, D9 and D51 samples are respectively found by 7 days after the first drug application: 42.84-54.90-52.31-47.00%, 42.64% and 41.83% of control effect of 2000 times of Naidi, preferably 750 times of control effect; over time, the control effect is improved to different degrees in 7 days after the second application, the control effect of the D29 and D9 samples on the anthracnose on the pepper fruits can reach more than 65%, and the control effect of the D2 and D51 samples can reach about 51.71% and 53.23% respectively, which are equivalent to 2000 times of Naidi stability (53.80%) and 750 times of Zhengjian (52.32%) of a control medicament.
EXAMPLE 145 test for controlling Rice blast with dicarboxylic acid Compound
1. Test conditions
1) And (3) test crops: rice (Menggu rice variety)
Test subjects: blast of rice
Test site: liaoning Panjin City
2) Test agents: d2, D29, D9, D51 and D68
3) The concentration of the medicament: 100ppm of
4) The spraying period is as follows: breaking and heading stages
5) Control solvent concentration: 1% DMSO
2. Experimental protocol
The method comprises the steps of adopting a five-point random sampling investigation method, investigating 10 plants at each point, counting the area of rice blast fungus scabs, adopting an international classification method, investigating 14 days after application of the pesticide, and counting disease indexes of the treated plants.
3. Test results
TABLE 28 test for control of Rice blast by dicarboxylic acid Compounds
The test result shows that: as can be seen from the whole test process, the blast disease does not occur before the pesticide is sprayed, and after the pesticide is sprayed twice, the control effects of the D2, D29, D9, D5 and D68 samples are 1000 times respectively: 72.18-42.90-6.30-74.67-41.00 percent, and shows that the two medicaments D2 and D51 have better protection and control effects on rice blast, and the control effects of D29 and D68 are lower, and are both about 50 percent. The sample D9 had poor control effect, and had almost no protection and control effect against rice blast.
Although the invention has been described in detail hereinabove by way of general description, specific embodiments and experiments, it will be apparent to those skilled in the art that many modifications and improvements can be made thereto without departing from the spirit and scope of the invention. Accordingly, it is intended that all such modifications and improvements be included within the scope of the invention without departing from the spirit thereof.
Claims (8)
1. The use of dicarboxylic acid compounds selected from the group consisting of compounds of formulae I, II, III and IV, isomers, hydrates or salts thereof for controlling plant diseases,
wherein n is an integer of 0 to 100, i.e., the compound has 0 to 100 carbons; m is an integer of 1-50, namely the part of the compound is 1-50 olefinic bonds; x is an integer of 0 to 50, i.e., the compound has 0 to 50 carbons; r is alkyl, alkoxy, aryl, aryloxy, heteroaryl, heteroaryloxy, alkenyl, alkynyl, hydroxyl, amino, fluorine, chlorine, bromine, iodine, nitro, nitroso, carboxyl, acyl, cyano or glycosyl.
2. The use according to claim 1, wherein the compound of formula I has a carboxyl function at both ends of the chain, n is 0 to 30, i.e. the part of the compound is 0 to 30 carbons; m is 1-16, i.e. the part of the compound is 1-16 olefinic bonds.
3. The use according to claim 1, wherein the compound of formula II has a carboxyl function at both ends of the chain, and n is 0 to 48, i.e. the part of the compound is 0 to 48 carbons.
4. The use according to claim 1, wherein the compound of formula III has a carboxyl function at both ends of the chain, n is 0 to 30, i.e. the part of the compound is 0 to 30 carbons; x is 0 to 30, i.e., the compound has 0 to 30 carbons.
5. The use according to claim 1, wherein the compound of formula IV has a carboxyl function at both ends of the chain, n is 0 to 10, i.e. the part of the compound is 0 to 10 carbons; x is 0 to 10, i.e., the compound has 0 to 10 carbons.
6. Use according to claim 2, wherein the compound of formula I is a compound selected from formula V.
7. Use according to claim 1, characterized in that the dicarboxylic acid compound is used as a plant protectant or fungicide.
8. The use of claim 1, wherein the dicarboxylic acid compound is used for controlling rice blast, anthracnose, downy mildew, phytophthora root rot and gray mold of plants.
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