CN1613847A - Aromatic diamidine compound with bactericidal activity and application thereof - Google Patents
Aromatic diamidine compound with bactericidal activity and application thereof Download PDFInfo
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- CN1613847A CN1613847A CN 200410073073 CN200410073073A CN1613847A CN 1613847 A CN1613847 A CN 1613847A CN 200410073073 CN200410073073 CN 200410073073 CN 200410073073 A CN200410073073 A CN 200410073073A CN 1613847 A CN1613847 A CN 1613847A
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- aromatic diamidine
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- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 13
- -1 Aromatic diamidine compound Chemical class 0.000 title claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 59
- 238000002360 preparation method Methods 0.000 claims abstract description 35
- 239000000203 mixture Substances 0.000 claims description 31
- 230000000855 fungicidal effect Effects 0.000 claims description 28
- 239000013543 active substance Substances 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 239000000945 filler Substances 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 238000009472 formulation Methods 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- YBVNFKZSMZGRAD-UHFFFAOYSA-N pentamidine isethionate Chemical compound OCCS(O)(=O)=O.OCCS(O)(=O)=O.C1=CC(C(=N)N)=CC=C1OCCCCCOC1=CC=C(C(N)=N)C=C1 YBVNFKZSMZGRAD-UHFFFAOYSA-N 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 7
- DSNYFFJTZPIKFZ-UHFFFAOYSA-N propoxybenzene Chemical class CCCOC1=CC=CC=C1 DSNYFFJTZPIKFZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000000645 desinfectant Substances 0.000 claims description 5
- 239000003921 oil Substances 0.000 claims description 5
- 238000005507 spraying Methods 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 3
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 claims description 3
- 239000006229 carbon black Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 239000010703 silicon Substances 0.000 claims description 3
- 239000002689 soil Substances 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- 239000000375 suspending agent Substances 0.000 claims description 3
- 239000004563 wettable powder Substances 0.000 claims description 3
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 25
- 244000052616 bacterial pathogen Species 0.000 abstract description 8
- 239000003899 bactericide agent Substances 0.000 abstract description 4
- 238000005516 engineering process Methods 0.000 abstract description 4
- 230000002401 inhibitory effect Effects 0.000 abstract description 3
- 230000012010 growth Effects 0.000 abstract description 2
- 239000004480 active ingredient Substances 0.000 abstract 1
- 244000000005 bacterial plant pathogen Species 0.000 abstract 1
- 239000002552 dosage form Substances 0.000 abstract 1
- 239000000575 pesticide Substances 0.000 abstract 1
- 239000003814 drug Substances 0.000 description 26
- 201000010099 disease Diseases 0.000 description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 20
- 235000013399 edible fruits Nutrition 0.000 description 17
- 230000002265 prevention Effects 0.000 description 15
- 241000196324 Embryophyta Species 0.000 description 14
- 241000894006 Bacteria Species 0.000 description 13
- 206010039509 Scab Diseases 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 10
- 240000003768 Solanum lycopersicum Species 0.000 description 10
- 230000003449 preventive effect Effects 0.000 description 10
- 239000007788 liquid Substances 0.000 description 8
- 239000000417 fungicide Substances 0.000 description 7
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- 238000013329 compounding Methods 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 244000037666 field crops Species 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- 238000011835 investigation Methods 0.000 description 5
- 241001465180 Botrytis Species 0.000 description 4
- 240000008067 Cucumis sativus Species 0.000 description 4
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 4
- 230000000857 drug effect Effects 0.000 description 4
- 108020004414 DNA Proteins 0.000 description 3
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- ABUGVBRDFWGJRD-CHOYNLESSA-N [9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-methyloxolan-2-yl]-2-(2,4-dinitrophenyl)sulfanylpurin-6-yl] [hydroxy(phosphonooxy)phosphoryl] hydrogen phosphate Chemical compound O[C@@H]1[C@H](O)[C@@H](C)O[C@H]1N1C2=NC(SC=3C(=CC(=CC=3)[N+]([O-])=O)[N+]([O-])=O)=NC(OP(O)(=O)OP(O)(=O)OP(O)(O)=O)=C2N=C1 ABUGVBRDFWGJRD-CHOYNLESSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 3
- 238000005070 sampling Methods 0.000 description 3
- 244000291564 Allium cepa Species 0.000 description 2
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 2
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- 241000499436 Brassica rapa subsp. pekinensis Species 0.000 description 2
- 235000016623 Fragaria vesca Nutrition 0.000 description 2
- 240000009088 Fragaria x ananassa Species 0.000 description 2
- 235000011363 Fragaria x ananassa Nutrition 0.000 description 2
- 239000005867 Iprodione Substances 0.000 description 2
- CFZLNRGUBAVQNO-UHFFFAOYSA-N N-(3,5-Dichlorophenyl)succinimide Chemical compound ClC1=CC(Cl)=CC(N2C(CCC2=O)=O)=C1 CFZLNRGUBAVQNO-UHFFFAOYSA-N 0.000 description 2
- 235000010726 Vigna sinensis Nutrition 0.000 description 2
- 244000042314 Vigna unguiculata Species 0.000 description 2
- 235000009754 Vitis X bourquina Nutrition 0.000 description 2
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- 240000006365 Vitis vinifera Species 0.000 description 2
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- 239000003905 agrochemical Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- ONUFESLQCSAYKA-UHFFFAOYSA-N iprodione Chemical compound O=C1N(C(=O)NC(C)C)CC(=O)N1C1=CC(Cl)=CC(Cl)=C1 ONUFESLQCSAYKA-UHFFFAOYSA-N 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
- 208000031295 Animal disease Diseases 0.000 description 1
- 235000000832 Ayote Nutrition 0.000 description 1
- 241000499339 Botrytis allii Species 0.000 description 1
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- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 241001674939 Caulanthus Species 0.000 description 1
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- 240000001980 Cucurbita pepo Species 0.000 description 1
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- 102000053602 DNA Human genes 0.000 description 1
- 241000628997 Flos Species 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- 241000223195 Fusarium graminearum Species 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- 235000003228 Lactuca sativa Nutrition 0.000 description 1
- 239000005805 Mepanipyrim Substances 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 241000736122 Parastagonospora nodorum Species 0.000 description 1
- 241000233616 Phytophthora capsici Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
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- CIFWZNRJIBNXRE-UHFFFAOYSA-N mepanipyrim Chemical compound CC#CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 CIFWZNRJIBNXRE-UHFFFAOYSA-N 0.000 description 1
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- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention discloses an aromatic diamidine compound with bactericidal activity, which can be used for inhibiting the growth of pathogenic bacteria and has special effect on gray mold. The compound can be prepared into various dosage forms and preparation forms, the content of active ingredients in each preparation form can be determined according to the specific compound related to the invention and the physicochemical properties of the compound, and each preparation can be used in the field by adopting the current commonly used pesticide field use technology. The invention applies the compound with bactericidal activity to prevent and treat plant pathogenic bacteria for the first time, and the compound is used as an agricultural bactericide.
Description
Technical field
The present invention relates to the disinfectant use in agriculture category, particularly the compound of aromatic diamidine fungicidal activity and application thereof.
Background technology
Phytopathogen has very big harm to the growth of plant, and all cause tremendous loss to agriculture production every year.Be the generation of controlling plant diseases, reduce that people have worked out the compound of big measurer sterilization and bacteriostatic activity, the generation that is used to prevent and treat and alleviate Plant diseases by its loss that causes.
Grey mold belongs to germ and comprises botrytis (B.cinera), green onion botrytis (B.allii) green onion squama botrytis (B.squamous) etc., and wherein Botrytis cinerea bacterium (B.cinera) is a kind of serious phytopathogen that endangers.Ash arrhizus bacteria can infect various plants, and wherein a lot of plants are important farm crop.Being subject to the plant that ash arrhizus bacteria infects has: the real plant of fresh fruit such as grass is mould, grape, apple and citrus etc.; Vegetables such as wild cabbage, Radix Dauci Sativae, cucumber, tomato, lettuce etc.; Ornamental plant such as rose, Flower of Evans Begonia, chrysanthemum, Flos Pelargonii, turmeric etc.Infecting of gray mold can cause the death of big area plant, thereby causes tremendous loss.
Summary of the invention
Defective or deficiency at above-mentioned prior art existence, the objective of the invention is to, compound of a kind of aromatic diamidine fungicidal activity and uses thereof is provided, this compound belongs to the brand-new compound of a class, gray mold there is special efficacy, can be used as the application of disinfectant use in agriculture at the control phytopathogen.
Aromatic diamidine Fungicidal active compound of the present invention is an object lesson with following two compounds: 4, and 4 '-diamidino-1,3-two phenoxypropanes; 4,4 '-two amidine azoles bases-1,3-(2,2 '-dimethoxy) two phenoxypropanes have been applied when several Animal diseases of treatment, and the present invention applies it in the control of phytopathogen first, promptly uses as disinfectant use in agriculture.
The technical solution adopted in the present invention is that the compound of aromatic diamidine fungicidal activity is characterized in that this structural general formula is:
Wherein: R
1=H, OCH
3
Other characteristics of the present invention are that described bactericidal compound can be made into various formulations or preparation, is used for spraying and uses;
The weight percent of each component is in each formulation:
| Formulation | Compound % | Filler or solvent % | Tensio-active agent % |
| Wettable powder | ????20～90 | ????0～74 | ????1～10 |
| Missible oil or soluble thick agent | ????5～50 | ????40～95 | ????0～35 |
| Water suspending agent | ????10～50 | ????40～84 | ????1～20 |
| Pulvis | ????1～25 | ????70～99 | ????0～5 |
| Granula or tablet | ????1～95 | ????5～99 | ????0～15 |
| Aqua | ????2～95 | ????5～98 | ????0～10 |
The various preparations that described bactericidal compound is formed, filler wherein can be one or more mixtures in the known materials of this area staff such as white carbon black, wilkinite, silicon bath soil; Solvent can be methyl alcohol, ethanol, one or more mixtures in the known material of this area staff such as (different) third alcohol and water just; Tensio-active agent can be one or more a mixture of those skilled in the art's all kinds of surfactants known and commonly used.
The various preparations that described bactericidal compound is formed also can add other Fungicidal active substances of 0.1%～70%.
Other Fungicidal active substances that add in the described various preparation are a kind of of the commonly used or known Fungicidal active substance of those skilled in the art in this area.
Another characteristics of the present invention are, can be applied to prevent and treat phytopathogen, use as disinfectant use in agriculture;
In structural general formula, work as R
1=H, R
2Be amidino groups, n is 3 o'clock, is 4,4 '-diamidino-1,3-two phenoxypropanes; Work as R
1=OCH
3, R
2Be amidine azoles base, n is 3 o'clock, is 4,4 '-two amidine azoles bases-1,3-(2,2 '-dimethoxy) two phenoxypropanes.
Four, embodiment
Implementation process of the present invention below is described in detail in detail.
Bactericidal compound is characterized in that this structural general formula is:
Comprise that structural general formula is:
Wherein: R
1=H, OCH
3
The bactericidal mechanism of described compound is: the double-stranded DNA ditch combination of compound energy and pathogenic bacteria, and especially with the zone of being rich in A, T base pair.The DNA that many phytopathogens, particularly plant grey mold belong to germ is a duplex structure, is rich in A, T base pair, therefore plant botrytis is had special efficacy, and the dna structure phytopathogen identical with the ash arrhizus bacteria constructional feature also had good preventive effect.
The application of tool Fungicidal active compound of the present invention is characterized in that this compound can be mixed with various formulations and preparation form, is used for the field control phytopathogen.The weight percent of each composition is in each preparation:
| Formulation | Compound % | Filler or solvent % | Tensio-active agent % |
| Wettable powder | ????20～90 | ????0～74 | ????1～10 |
| Missible oil or soluble thick agent | ????5～50 | ????40～95 | ????0～35 |
| Water suspending agent | ????10～50 | ????40～84 | ????1～20 |
| Pulvis | ????1～25 | ????70～99 | ????0～5 |
| Granula or tablet | ????1～95 | ????5～99 | ????0～15 |
| Aqua | ????2～95 | ????5～98 | ????0～10 |
Filler wherein is one or more mixtures in the known materials of this area staff such as white carbon black, wilkinite, silicon bath soil; Solvent is methyl alcohol, ethanol, one or more mixtures in (different) third alcohol and water and the known material of this area staff just; Tensio-active agent can be one or more a mixture of the commonly used and known all kinds of surfactants of those skilled in the art.
By the various preparations that compound is formed, it is characterized in that also can adding in each preparation other fungicide active substances of 0.1～70%.Other fungicidal activity compositions that add in the various preparations can be used always in this area, are the known Fungicidal active substance of those skilled in the art.
The content of effective ingredient can be determined according to the particular compound that the present invention relates to and its physico-chemical property in each preparation form, each preparation can adopt current agricultural chemicals field use technology commonly used to use in the field, and these current agricultural chemicals field use technologys commonly used are known to those skilled in the art.
The present invention can provide by following embodiment:
Embodiment 1: in the compound structure general formula, work as R
2For
N is 3, R
1During for H (hereinafter to be referred as W1), structural formula is:
Embodiment 2: in the compound structure general formula, work as R
2For
N is 3, R
1During for H (hereinafter to be referred as W2), structural formula is:
Embodiment 3: in the compound structure general formula, work as R
1Be H, R
2For
N is 3 o'clock (hereinafter to be referred as W3), and structural formula is:
Embodiment 4: in the compound structure general formula, work as R
1Be OCH
3, R
2For
N is 3 o'clock (hereinafter to be referred as W4), and structural formula is:
Embodiment 5: in the compound structure general formula, work as R
1Be OCH
3, R
2For
, n is 4 o'clock (hereinafter to be referred as W5), structural formula is:
Embodiment 6: in the compound structure general formula, work as R
1Be OCH
3, R
2For
N is 5 o'clock (hereinafter to be referred as W6), and structural formula is:
EXPERIMENTAL EXAMPLE 1
Under isolated condition, compound W1, W2, W3, W4, W5 and W6 are effective to the various plants pathogenic bacteria.Each compound is mixed with the medicament of 10mg/L with sterilized water, with botrytis cinerea, the leaf muld of tomato bacterium, tomato early blight bacterium, the Chinese cabbage alternaria, 12 kind of plant germs such as fusarium graminearum are for biological for examination, the 1ml soup is added in the PDA substratum of 9ml and mixes, pour into and make band medicine substratum in the culture dish of high-temperature sterilization, after treating culture medium solidifying, each substratum plane is put into 1 for examination bacterium cake, contrast is put 1 for examination bacterium cake (diameter is 4mm), each is handled 3 times and repeats, according to the contrast growing state, measure for the examination colony diameter with the right-angled intersection method, calculate inhibiting rate, the results are shown in Table 1 with following formula
Table 1 compound is to the inhibition effect of different phytopathogens
| Inhibiting rate (%) | |||||||||
| Sample | Botrytis cinerea (3d) | Leaf muld of tomato bacterium (3d) | Tomato early blight bacterium (3d) | Chinese cabbage alternaria (4d) | Cucumber fusarium axysporum (4d) | Dry rot of apple bacterium (4d) | Phytophthora capsici germ (4d) | Tobacco brown spot pathogen (3d) | Pumpkin wilt (3d) |
| ??W1 | ????96.8 | ????53.2 | ????66.1 | ????96.4 | ????30.4 | ????90.4 | ????40.9 | ????93.3 | ????38.1 |
| ??W2 | ????97.8 | ????73.2 | ????68.7 | ????98.7 | ????56.6 | ????93.6 | ????67.8 | ????95.8 | ????78.5 |
| ??W3 | ????76.8 | ????48.9 | ????65.6 | ????87.5 | ????30.2 | ????87.3 | ????35.6 | ????76.9 | ????36.8 |
| ??W4 | ????98.7 | ????69.8 | ????76.8 | ????98.7 | ????46.9 | ????92.6 | ????48.7 | ????95.7 | ????56.8 |
| ??W5 | ????96.9 | ????83.9 | ????86.3 | ????98.9 | ????86.4 | ????95.1 | ????86.7 | ????96.6 | ????88.9 |
| ??W6 | ????78.5 | ????56.2 | ????67.8 | ????88.6 | ????56.4 | ????88.6 | ????63.5 | ????85.2 | ????59.7 |
EXPERIMENTAL EXAMPLE 2:
Compound W1, W2, W3, W4, W5 and W6 among the embodiment 2 are effective to the various plants pathogenic bacteria.Each compound is dissolved among 5% the polyethylene Glycol, is sprayed on the plant, at 24 ℃ of following airings.Inoculate pathogenic bacteria then, grew surely 5-7 days, check the growth of pathogenic bacteria situation.Prevention effect is represented with 0 (contrast) to 10 (100%) index, be the results are shown in Table 2.
Table 2 compound is to the prevention effect of different germs
| Concentration (PPM) | B.Cinera (apple) | B.Cinera (grape leaf) | S.nodorum (wheat leaf blade) | |
| ????W1 | ??200 | ????9 | ????9 | ????8 |
| ??60 | ????9 | ????8 | ????6 | |
| ??20 | ????8 | ????7 | ????4 | |
| ??6 | ????7 | ????6 | ????0 | |
| ????W2 | ??200 | ????10 | ????0 | ????3 |
| ??60 | ????9 | ????0 | ????0 | |
| ??20 | ????8 | ????0 | ????0 | |
| ??6 | ????6 | ????0 | ????0 | |
| ????W3 | ??200 | ????8 | ????9 | ????8 |
| ??60 | ????7 | ????8 | ????7 | |
| ??20 | ????7 | ????7 | ????6 | |
| ??6 | ????5 | ????5 | ????0 | |
| ????W4 | ??200 | ????10 | ????10 | ????10 |
| ??60 | ????9 | ????9 | ????8 | |
| ??20 | ????8 | ????9 | ????7 | |
| ??6 | ????7 | ????7 | ????7 | |
| ????W5 | ??200 | ????10 | ????10 | ????9 |
| ??60 | ????9 | ????9 | ????8 | |
| ??20 | ????8 | ????9 | ????7 | |
| ??6 | ????7 | ????8 | ????6 | |
| ????W6 | ??200 | ????8 | ????9 | ????7 |
| ??60 | ????8 | ????7 | ????7 | |
| ??20 | ????6 | ????7 | ????6 | |
| ??6 | ????6 | ????6 | ????0 |
EXPERIMENTAL EXAMPLE 3:
With W1, W2, W3, W4, W5 and W6 compounding method of preparation of the present invention, be mixed with 2% aqua, carried out the test of control phytopathogen in the land for growing field crops, with common fungicide iprodione and Sukeling is the contrast medicament, clear water is for contrast, the prevention effect behind the different concns medicine liquid spray sees Table 3, table 4.
In experiment, for various preparations, filler or the solvent of compound composition, the weight percent of tensio-active agent, and the per-cent that adds other Fungicidal active substances, by technical scheme preparation of the present invention, all can reach the ideal effect.
Cucumber, graw mold of tomato take place and the prevention effect investigation, mainly are the respondent with the fruit.5 samplings are adopted in every sub-district, and every some investigation 2～3 strains, every strain are investigated 3～5 fruits and carried out record according to following grade scale.According to following grade scale record blade incidence, calculate prevention effect according to disease index, the significance of difference between each is handled with the analysis of DMRT method.
0 grade: fruit does not have scab;
1 grade: the scab diameter is less than 1cm;
3 grades: scab diameter 1～2cm;
5 grades: scab diameter 2～3cm;
7 grades: scab diameter 3～4cm;
9 grades: the scab diameter is greater than 5cm.
The state of an illness radix of investigation gray mold before the dispenser, the dispenser " Invest, Then Investigate " fruit state of an illness and record.
If not morbidity (being that state of an illness radix is 0) then is calculated as follows relative control effect before the reagent.
Table 3 2% compound aqua control cucumber grey mold test-results
| Medicament | Concentration | Average disease index | Prevention effect (%) | The significance of difference (α=0.05) |
| ????W1 | ????50PPM | ????10.59 | ????61.9 | ????c |
| ????100PPM | ????7.44 | ????68.0 | ????b | |
| ????200PPM | ????5.56 | ????79.8 | ????a | |
| ????W2 | ????50PPM | ????9.59 | ????61.9 | ????c |
| ????100PPM | ????8.44 | ????66.0 | ????b | |
| ????200PPM | ????5.86 | ????78.8 | ????a | |
| ????W3 | ????50PPM | ????10.89 | ????41.9 | ????c |
| ????100PPM | ????9.44 | ????61.0 | ????b | |
| ????200PPM | ????6.56 | ????66.8 | ????a | |
| ????W4 | ????50PPM | ????9.79 | ????65.9 | ????c |
| ????100PPM | ????8.74 | ????71.0 | ????b | |
| ????200PPM | ????5.36 | ????80.8 | ????a | |
| ????W5 | ????50PPM | ????10.19 | ????59.9 | ????c |
| ????100PPM | ????8.44 | ????67.0 | ????b | |
| ????200PPM | ????5.26 | ????79.8 | ????a | |
| ????W6 | ????50PPM | ????11.98 | ????52.9 | ????c |
| ????100PPM | ????9.44 | ????66.0 | ????b | |
| ????200PPM | ????7.56 | ????72.8 | ????a | |
| Iprodione | 1000 times of liquid | ????7.17 | ????74.2 | ????a |
| Blank | ????------- | ????27.8 | ????------ | ????------ |
Table 4 2% compound aqua control tomato grey mold test-results
| Medicament | Concentration | Average disease index | Prevention effect (%) | The significance of difference |
| ??p 0.05????p 0.01 | ||||
| ????W1 | ????50PPM | ????0.097 | ????62.11 | ??c?????????C |
| ????100PPM | ????0.084 | ????67.19 | ??b?????????B | |
| ????200PPM | ????0.064 | ????75.00 | ??a?????????A | |
| ????W2 | ????50PPM | ????0.092 | ????65.11 | ??c?????????C |
| ????100PPM | ????0.074 | ????69.19 | ??b?????????B | |
| ????200PPM | ????0.054 | ????79.00 | ??a?????????A | |
| ????W3 | ????50PPM | ????0.098 | ????58.11 | ??c?????????C |
| ????100PPM | ????0.084 | ????63.19 | ??b?????????B | |
| ????200PPM | ????0.066 | ????69.00 | ??a?????????A | |
| ????W4 | ????50PPM | ????0.089 | ????64.11 | ??c?????????C |
| ????100PPM | ????0.076 | ????78.29 | ??b?????????B | |
| ????200PPM | ????0.058 | ????80.20 | ??a?????????A | |
| ????W5 | ????50PPM | ????0.091 | ????65.11 | ??c?????????C |
| ????100PPM | ????0.075 | ????69.19 | ??b?????????B | |
| ????200PPM | ????0.047 | ????82.70 | ??a?????????A | |
| ????W6 | ????50PPM | ????0.098 | ????61.11 | ??c?????????C |
| ????100PPM | ????0.088 | ????66.19 | ??b?????????B | |
| ????200PPM | ????0.068 | ????71.00 | ??a?????????A | |
| Sukeling | 1500 times of liquid | ????0.14 | ????45.31 | ??d?????????D |
| Blank | ????------- | ????0.256 | ????------ | ??-----?????----- |
EXPERIMENTAL EXAMPLE 4:
With W1, W2, W3, W4, W5 and W6 compounding method of preparation of the present invention, being mixed with 5% soluble granula, having carried out the test of control cowpea ash arrhizus bacteria in the land for growing field crops, is the contrast medicament with the common fungicide Sukeling, clear water is contrast, and the prevention effect behind the different concns medicine liquid spray sees Table 5.
In experiment, for various preparations, filler or the solvent of compound composition, the weight percent of tensio-active agent, and the per-cent that adds other Fungicidal active substances, by technical scheme preparation of the present invention, all can reach the ideal effect.
Diagonal lines 5 samplings in every sub-district whenever click 2 strains totally 10 strains.According to following grade scale record blade incidence, calculate prevention effect according to disease index, the significance of difference between each is handled with the analysis of DMRT method.
Sick leaf grade scale:
0 grade: no scab; 1 grade: sick portion accounts for below 5% of leaf area; 3 grades: sick portion accounts for the 6-15% of leaf area; 5 grades: sick portion accounts for the 16-25% of leaf area; 7 grades: sick portion accounts for the 26-50% of leaf area; 9 grades: sick portion accounts for more than 50% of leaf area.
If not morbidity (being that state of an illness radix is 0) then is calculated as follows relative control effect before the reagent.
Table 5 5% compound soluble granula control cowpea gray mold drug effect (blade)
| The medicament title | Spraying medicine concentration (mg/L) | Disease refers to (%) before the medicine | After the 2nd dispenser 7 days | After the 4th dispenser 7 days | ||||||
| Disease index (%) | Preventive effect (%) | The significance of difference | Disease index (%) | Preventive effect (%) | The significance of difference | |||||
| ??0.05????0.01 | ??0.05????0.01 | |||||||||
| ??W1 | ??200 | ??0 | ????1.35 | ??80.66 | ??a | ??A | ????2.50 | ??76.98 | ??a | ??A |
| ??100 | ??0 | ????1.78 | ??74.50 | ??b | ??B | ????3.01 | ??72.28 | ??b | ??B | |
| ??50 | ??0 | ????2.82 | ??59.60 | ??c | ??C | ????4.65 | ??57.18 | ??c | ??C | |
| ??W2 | ??200 | ??0 | ????1.27 | ??83.62 | ??a | ??A | ????2.42 | ??79.98 | ??a | ??A |
| ??100 | ??0 | ????1.68 | ??76.53 | ??b | ??B | ????2.81 | ??75.08 | ??b | ??B | |
| ??50 | ??0 | ????2.23 | ??61.62 | ??c | ??C | ????4.35 | ??59.18 | ??c | ??C | |
| ??W3 | ??200 | ??0 | ????1.65 | ??72.66 | ??a | ??A | ????2.58 | ??73.91 | ??a | ??A |
| ??100 | ??0 | ????1?98 | ??70.50 | ??b | ??B | ????3.21 | ??70.23 | ??b | ??B | |
| ??50 | ??0 | ????2.96 | ??52.60 | ??c | ??C | ????4.75 | ??55.17 | ??c | ??C | |
| ??W4 | ??200 | ??0 | ????1.15 | ??85.61 | ??a | ??A | ????2.43 | ??82.98 | ??a | ??A |
| ??100 | ??0 | ????1.58 | ??78.50 | ??b | ??B | ????2.81 | ??79.61 | ??b | ??B | |
| ??50 | ??0 | ????2.72 | ??63.60 | ??c | ??C | ????4.05 | ??67.18 | ??c | ??C | |
| ??W5 | ??200 | ??0 | ????1.25 | ??82.66 | ??a | ??A | ????2.38 | ??83.68 | ??a | ??A |
| ??100 | ??0 | ????1.48 | ??78.57 | ??b | ??B | ????2.81 | ??79.87 | ??b | ??B | |
| ??50 | ??0 | ????2.72 | ??60.60 | ??c | ??C | ????4.25 | ??65.19 | ??c | ??C | |
| ??W6 | ??200 | ??0 | ????1.45 | ??79.66 | ??a | ??A | ????2.59 | ??75.97 | ??a | ??A |
| ??100 | ??0 | ????1.68 | ??75.50 | ??b | ??B | ????3.31 | ??70.08 | ??b | ??B | |
| ??50 | ??0 | ????2.72 | ??61.67 | ??c | ??C | ????4.85 | ??52.19 | ??c | ??C | |
| 50% Sukeling | ??500 | ??0 | ????1.91 | ??72.64 | ??b | ??B | ????3.18 | ??70.72 | ??b | ??B |
| Blank | Clear water | ??0 | ????6.98 | ??- | ????10.86 | ??- | ||||
EXPERIMENTAL EXAMPLE 5:
With W1, W2, W3, W4, W5 and W6 compounding method of preparation of the present invention, being mixed with 2% missible oil, having carried out the test of control grey mould fruit rot of strawberry bacterium in the land for growing field crops, is the contrast medicament with common fungicide 40% dimetachlone, clear water is contrast, and the prevention effect behind the different concns medicine liquid spray sees Table 6.
In experiment, for various preparations, filler or the solvent of compound composition, the weight percent of tensio-active agent, and the per-cent that adds other Fungicidal active substances, by technical scheme preparation of the present invention, all can reach the ideal effect.
Investigation method is taked parallel lines 2 row samplings, and the incidence of the above fruit of every row investigation 1.5cm is by the generation classification of following grade scale to the fruit gray mold.Calculate prevention effect according to disease index, the significance of difference between each is handled with the analysis of DMRT method.
0 grade: fruit is not fallen ill;
1 grade: scab accounts for below 5% of whole fruit area;
3 grades: scab accounts for 6%～15% of whole fruit area;
5 grades: scab accounts for 16%～25% of whole fruit area;
7 grades: scab accounts for 26%～50% of whole fruit area;
9 grades: scab accounts for more than 50% of whole fruit area.
Table 6 2% compound missible oil is to the grey mould fruit rot of strawberry prevention effect
| The medicament title | Spraying medicine concentration (mg/l) | Disease refers to (%) before the medicine | After the dispenser d days | |||||
| ????????????3d | ????????????7d | ???????????14d | ||||||
| Disease refers to (%) | Preventive effect (%) | Disease refers to (%) | Preventive effect (%) | Disease refers to (%) | Preventive effect (%) | |||
| ??W1 | ????100 | ??1.68 | ??4.60 | ??69.89 | ??5.47 | ??76.09 | ??4.37 | ????84.49 |
| ????200 | ??1.76 | ??4.09 | ??82.76 | ??5.62 | ??78.89 | ??3.58 | ????89.08 | |
| ??W2 | ????100 | ??1.88 | ??4.53 | ??71.79 | ??5.17 | ??79.25 | ??4.37 | ????84.49 |
| ????200 | ??1.76 | ??3.89 | ??85.76 | ??5.52 | ??80.89 | ??3.68 | ????88.08 | |
| ??W3 | ????100 | ??1.78 | ??4.63 | ??66.79 | ??5.47 | ??76.09 | ??4.57 | ????80.49 |
| ????200 | ??1.96 | ??4.29 | ??71.76 | ??5.72 | ??76.89 | ??3.87 | ????79.98 | |
| ??W4 | ????100 | ??1.78 | ??4.57 | ??72.79 | ??5.37 | ??77.90 | ??4.37 | ????84.49 |
| ????200 | ??1.96 | ??4.29 | ??71.76 | ??5.64 | ??76.89 | ??3.92 | ????89.78 | |
| ??W5 | ????100 | ??1.78 | ??4.20 | ??76.79 | ??5.07 | ??82.59 | ??4.37 | ????88.49 |
| ????200 | ??1.96 | ??4.29 | ??78.83 | ??5.62 | ??85.89 | ??3.38 | ????89.92 | |
| ??W6 | ????100 | ??1.78 | ??4.56 | ??64.77 | ??5.49 | ??76.09 | ??4.37 | ????84.49 |
| ????200 | ??1.96 | ??4.29 | ??76.66 | ??5.72 | ??83.89 | ??3.68 | ????89.38 | |
| 40% dimetachlone wp | ????800 | ??2.10 | ??5.79 | ??64.36 | ??7.02 | ??73.53 | ??5.36 | ????83.83 |
| Contrast | ??2.26 | ??17.40 | ??28.52 | ??35.47 | ||||
EXPERIMENTAL EXAMPLE 6:
With 2% compound W2 and the mould prestige of 5% second, adopt compounding method of preparation of the present invention, be mixed with 7% mixed bactericide, carried out the test of control botrytis cinerea in the land for growing field crops, with common fungicide 50% Sukeling is the contrast medicament, clear water is contrast, and the prevention effect behind the different concns medicine liquid spray sees Table 7.
In experiment, for various preparations, filler or the solvent of compound composition, the weight percent of tensio-active agent, and the per-cent that adds other Fungicidal active substances, by technical scheme preparation of the present invention, all can reach the ideal effect.
The mould prestige mixture control of table 7 7%W2 second graw mold of tomato drug effect (fruit)
| Medicament | For examination concentration (mg/L) | Disease refers to % before the medicine | After the 2nd dispenser 7 days | The significance of difference | After the 4th dispenser 7 days | The significance of difference | ||||
| Disease refers to % | Preventive effect (%) | ????0.05 | ????0.01 | Disease refers to % | Preventive effect (%) | ??0.05 | ???0.01 | |||
| The mould prestige mixture of 7%W2 second | ??200 | ??0 | ????0.09 | ??78.57 | ????a | ????A | ????2.32 | ????80.41 | ??a | ??A |
| ??100 | ??0 | ????0.13 | ??70.05 | ????c | ????C | ????3.11 | ????73.73 | ??b | ??B | |
| ??50 | ??0 | ????0.19 | ??54.76 | ????d | ????D | ????4.20 | ????64.53 | ??c | ??C | |
| Sukeling | ??500 | ??0 | ????0.11 | ??74.81 | ????b | ????B | ????2.46 | ????80.22 | ??a | ??A |
| Blank | ??- | ??0 | ????0.42 | ??- | ????11.84 | ????- | ||||
EXPERIMENTAL EXAMPLE 7:
With 4% compound W1 and 15% derosal, adopt compounding method of preparation of the present invention, be mixed with 19% mixed bactericide, carried out the test of control botrytis cinerea in the land for growing field crops, with common fungicide 50% derosal is the contrast medicament, clear water is contrast, and the prevention effect behind the different concns medicine liquid spray sees Table 8.
In experiment, for various preparations, filler or the solvent of compound composition, the weight percent of tensio-active agent, and the per-cent that adds other Fungicidal active substances, by technical scheme preparation of the present invention, all can reach the ideal effect.
Table 8 19%W1 derosal mixture control graw mold of tomato drug effect (fruit)
EXPERIMENTAL EXAMPLE 8:
With 2% compound W5 and 10% mepanipyrim, adopt compounding method of preparation of the present invention, be mixed with 12% mixed bactericide, carried out the test of control botrytis cinerea in the land for growing field crops, executing good happy SC with common fungicide 40% is the contrast medicament, clear water is contrast, and the prevention effect behind the different concns medicine liquid spray sees Table 9.
In experiment, for various preparations, filler or the solvent of compound composition, the weight percent of tensio-active agent, and the per-cent that adds other Fungicidal active substances, by technical scheme preparation of the present invention, all can reach the ideal effect.
The phonetic mould amine mixture control graw mold of tomato drug effect (fruit) of table 9 12%W5
| Medicament | For examination concentration (mg/L) | Disease refers to before the medicine | After the 2nd dispenser 7 days | The significance of difference | After the 4th dispenser 7 days | The significance of difference | ||||
| Disease refers to (%) | Preventive effect (%) | ??0.05 | ???0.01 | Disease refers to (%) | Preventive effect (%) | ??0.05 | ?0.01 | |||
| The phonetic mould amine mixture of 12%W5 | ??200 ??100 ??50 | ??0 ??0 ??0 | ????8.32 ????9.42 ????12.43 | ????78.40 ????75.55 ????67.73 | ????a ????b ????c | ????A ????B ????C | ????15.12 ????17.64 ????21.45 | ????76.84 ????73.88 ????67.14 | ????a ????b ????c | ????A ????B ????C |
| 40% executes good happy SC | ??500 | ??0 | ????9.25 | ????75.99 | ????b | ????AB | ????17.35 | ????73.42 | ????b | ????B |
| Blank | ??- | ??0 | ????38.52 | ????- | ????65.28 | ????- | ||||
Claims (5)
1. the compound of aromatic diamidine fungicidal activity is characterized in that this structural general formula is:
Wherein: R
1=H, OCH
3
2. the compound of aromatic diamidine fungicidal activity as claimed in claim 1 is characterized in that, described compound can be processed into and be fit to various formulations or the preparation that spraying is used;
The weight percent of each material is in various formulations or the preparation:
Formulation Compound % Filler or solvent % Tensio-active agent %
Wettable powder ????20～90 ????0～74 ????1～10
Missible oil or soluble thick agent ????5～50 ????40～95 ????0～35
Water suspending agent ????10～50 ????40～84 ????1～20
Pulvis ????1～25 ????70～99 ????0～5
Granula or tablet ????1～95 ????5～99 ????0～15
Aqua ????2～95 ????5～98 ????0～10
Filler wherein is one or more mixtures in white carbon black, wilkinite, silicon bath soil and the known material of those skilled in the art; Solvent is one or more mixtures in the known material of methyl alcohol, ethanol, n-propyl alcohol, Virahol, water and those skilled in the art; Tensio-active agent is one or more a mixture of those skilled in the art's all kinds of surfactants known and commonly used.
3. bactericidal compound as claimed in claim 2 is characterized in that, in the described various formulations of being made up of compound or preparation, also adds a kind of of other commonly used or Fungicidal active substances well known in the art of 0.1%～70% in addition.
4. the compound of the described aromatic diamidine fungicidal activity of claim 1 is as the application of disinfectant use in agriculture at the control phytopathogen.
5. application as claimed in claim 4 in structural general formula, is worked as R
1Be H, R
2Be amidino groups, n is 3 o'clock, is 4,4 '-diamidino-1,3-two phenoxypropanes;
In the compound structure general formula, work as R
1Be OCH
3, R
2Be amidine azoles base, n is 2 o'clock, is 4,4 '-two amidine azoles bases-1,3-(2,2 '-dimethoxy) two phenoxypropanes.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200410073073 CN1613847A (en) | 2004-09-13 | 2004-09-13 | Aromatic diamidine compound with bactericidal activity and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200410073073 CN1613847A (en) | 2004-09-13 | 2004-09-13 | Aromatic diamidine compound with bactericidal activity and application thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1613847A true CN1613847A (en) | 2005-05-11 |
Family
ID=34765248
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 200410073073 Pending CN1613847A (en) | 2004-09-13 | 2004-09-13 | Aromatic diamidine compound with bactericidal activity and application thereof |
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| Country | Link |
|---|---|
| CN (1) | CN1613847A (en) |
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| CN103053530A (en) * | 2013-01-06 | 2013-04-24 | 广东中迅农科股份有限公司 | Bactericidal composition of propamidine and fluazinam |
| CN103416402A (en) * | 2013-07-22 | 2013-12-04 | 杨凌农科大无公害农药研究服务中心 | Propamidine water dispersible granule (WDG) and preparation method thereof |
| CN103518726A (en) * | 2013-10-12 | 2014-01-22 | 京博农化科技股份有限公司 | Sterilizing composition containing boscalid and propamidine |
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2004
- 2004-09-13 CN CN 200410073073 patent/CN1613847A/en active Pending
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| CN103053530A (en) * | 2013-01-06 | 2013-04-24 | 广东中迅农科股份有限公司 | Bactericidal composition of propamidine and fluazinam |
| CN103053530B (en) * | 2013-01-06 | 2014-09-17 | 广东中迅农科股份有限公司 | Bactericidal composition of propamidine and fluazinam |
| CN103416402B (en) * | 2013-07-22 | 2015-08-19 | 杨凌农科大无公害农药研究服务中心 | A kind of propamidine water dispersible granules and preparation method thereof |
| CN103416402A (en) * | 2013-07-22 | 2013-12-04 | 杨凌农科大无公害农药研究服务中心 | Propamidine water dispersible granule (WDG) and preparation method thereof |
| CN103518726B (en) * | 2013-10-12 | 2015-11-18 | 京博农化科技股份有限公司 | A kind of bactericidal composition containing Boscalid and propamidine |
| CN103518726A (en) * | 2013-10-12 | 2014-01-22 | 京博农化科技股份有限公司 | Sterilizing composition containing boscalid and propamidine |
| CN104285989A (en) * | 2014-09-10 | 2015-01-21 | 广东中迅农科股份有限公司 | Pesticide composition containing pyraclostrobin and propamidine |
| CN104285956A (en) * | 2014-09-10 | 2015-01-21 | 广东中迅农科股份有限公司 | Pesticide composition containing azoxystrobin and propamidine |
| CN104285989B (en) * | 2014-09-10 | 2017-06-23 | 广东中迅农科股份有限公司 | A kind of composition pesticide containing pyraclostrobin and propamidine |
| CN104285956B (en) * | 2014-09-10 | 2017-11-28 | 广东中迅农科股份有限公司 | A kind of composition pesticide containing Fluoxastrobin and propamidine |
| CN104322496A (en) * | 2014-09-15 | 2015-02-04 | 广东中迅农科股份有限公司 | Pesticide composition containing cyprodinil and propamidine |
| CN104322496B (en) * | 2014-09-15 | 2017-12-12 | 广东中迅农科股份有限公司 | A kind of composition pesticide containing cyprodinil and propamidine |
| CN104855390A (en) * | 2015-04-29 | 2015-08-26 | 京博农化科技股份有限公司 | Sterilization composition containing cyprokonazol and propamidine |
| CN104855390B (en) * | 2015-04-29 | 2016-09-14 | 京博农化科技股份有限公司 | A kind of bactericidal composition containing cyproconazole Yu propamidine |
| CN114190386A (en) * | 2021-12-01 | 2022-03-18 | 西北农林科技大学 | Compound composition of propamidine and sabinenol, bactericide and application |
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