CN105646347A - Naphthalimide aryl urea compound and application thereof - Google Patents
Naphthalimide aryl urea compound and application thereof Download PDFInfo
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- CN105646347A CN105646347A CN201610052863.2A CN201610052863A CN105646347A CN 105646347 A CN105646347 A CN 105646347A CN 201610052863 A CN201610052863 A CN 201610052863A CN 105646347 A CN105646347 A CN 105646347A
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- aryl urea
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- -1 Naphthalimide aryl urea compound Chemical class 0.000 title claims abstract description 11
- 239000004202 carbamide Substances 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- 239000005648 plant growth regulator Substances 0.000 claims abstract description 14
- 230000000694 effects Effects 0.000 claims abstract description 12
- 230000000844 anti-bacterial effect Effects 0.000 claims abstract description 11
- 239000000203 mixture Substances 0.000 claims description 10
- 230000000855 fungicidal effect Effects 0.000 claims description 2
- 230000003641 microbiacidal effect Effects 0.000 claims description 2
- 229940124561 microbicide Drugs 0.000 claims description 2
- 239000002855 microbicide agent Substances 0.000 claims description 2
- 208000031888 Mycoses Diseases 0.000 abstract description 5
- 230000012010 growth Effects 0.000 abstract description 5
- 230000008635 plant growth Effects 0.000 abstract description 2
- 230000001737 promoting effect Effects 0.000 abstract description 2
- 239000003899 bactericide agent Substances 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 10
- 241000894006 Bacteria Species 0.000 description 6
- 240000008067 Cucumis sativus Species 0.000 description 6
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 6
- 235000013399 edible fruits Nutrition 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 241000219095 Vitis Species 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 210000000582 semen Anatomy 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 235000017060 Arachis glabrata Nutrition 0.000 description 3
- 244000105624 Arachis hypogaea Species 0.000 description 3
- 235000010777 Arachis hypogaea Nutrition 0.000 description 3
- 235000018262 Arachis monticola Nutrition 0.000 description 3
- 241001157813 Cercospora Species 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 241000233616 Phytophthora capsici Species 0.000 description 3
- 235000009754 Vitis X bourquina Nutrition 0.000 description 3
- 235000012333 Vitis X labruscana Nutrition 0.000 description 3
- 235000014787 Vitis vinifera Nutrition 0.000 description 3
- 230000032823 cell division Effects 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 235000020232 peanut Nutrition 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 230000003449 preventive effect Effects 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 2
- HXJBFRDWVHNPAS-UHFFFAOYSA-N 2-aminobenzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(C(N(N)C2=O)=O)=C3C2=CC=CC3=C1 HXJBFRDWVHNPAS-UHFFFAOYSA-N 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 2
- 241000213004 Alternaria solani Species 0.000 description 2
- 241000555706 Botryosphaeria dothidea Species 0.000 description 2
- 241000395107 Cladosporium cucumerinum Species 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- 241000223218 Fusarium Species 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- GRSMWKLPSNHDHA-UHFFFAOYSA-N Naphthalic anhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=CC3=C1 GRSMWKLPSNHDHA-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 235000009392 Vitis Nutrition 0.000 description 2
- 244000052616 bacterial pathogen Species 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000010413 mother solution Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 235000010603 pastilles Nutrition 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- PRPINYUDVPFIRX-UHFFFAOYSA-N 1-naphthaleneacetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CC=CC2=C1 PRPINYUDVPFIRX-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- MRKGZSUOHWCQNB-UHFFFAOYSA-N 4-(1h-indol-2-yl)butanoic acid;sodium Chemical compound [Na].C1=CC=C2NC(CCCC(=O)O)=CC2=C1 MRKGZSUOHWCQNB-UHFFFAOYSA-N 0.000 description 1
- FRXSZNDVFUDTIR-UHFFFAOYSA-N 6-methoxy-1,2,3,4-tetrahydroquinoline Chemical compound N1CCCC2=CC(OC)=CC=C21 FRXSZNDVFUDTIR-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 241000198596 Alternaria tomatophila Species 0.000 description 1
- 229930192334 Auxin Natural products 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- 240000000560 Citrus x paradisi Species 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 240000001008 Dimocarpus longan Species 0.000 description 1
- 101100117236 Drosophila melanogaster speck gene Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 235000000235 Euphoria longan Nutrition 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241000233679 Peronosporaceae Species 0.000 description 1
- HFCYZXMHUIHAQI-UHFFFAOYSA-N Thidiazuron Chemical compound C=1C=CC=CC=1NC(=O)NC1=CN=NS1 HFCYZXMHUIHAQI-UHFFFAOYSA-N 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 230000003416 augmentation Effects 0.000 description 1
- 239000002363 auxin Substances 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 230000006806 disease prevention Effects 0.000 description 1
- 230000002554 disease preventive effect Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 230000008774 maternal effect Effects 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- LCRMGUFGEDUSOG-UHFFFAOYSA-N naphthalen-1-ylsulfonyloxymethyl naphthalene-1-sulfonate;sodium Chemical compound [Na].C1=CC=C2C(S(=O)(OCOS(=O)(=O)C=3C4=CC=CC=C4C=CC=3)=O)=CC=CC2=C1 LCRMGUFGEDUSOG-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229930195732 phytohormone Natural products 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/14—Aza-phenalenes, e.g. 1,8-naphthalimide
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a naphthalimide aryl urea compound with the structural formula shown in the formula I in the specification. The compound shown in the formula I has good bactericidal activity and can serve as a bactericide to prevent and treat fungal diseases of crops; the compound shown in the formula I further has the effects of promoting growth, increasing the yield and improving the quality, and can serve as a plant growth regulator to regulate growth of plants.
Description
Technical field
The invention belongs to antibacterial and plant growth regulator field in pesticide, be specifically related to a kind of aphthalimide base aryl urea compounds and application thereof.
Background technology
Auxins regulator is a kind of important kind of plant growth regulator, and it has promotion Cutting rooting, slow down aging or promotes organ to come off, controls the effects such as male and female sex, induced parthenocarpy. The prevention and control of plant diseases, pest control is also one of direction of volume increase, in crops and vegetable infectious disease, mainly has fungal disease and bacterial disease, and fungal disease is maximum to the harm of crops, even can result in the significantly underproduction. Along with the development of pesticide technology, its comprehensive and safety is subject to bigger attention, and if commercial TCC is typical antibacterial, Thidiazuron etc. is typical plant growth regulator. The plant growth regulator kind belonging to China's independent intellectual property right is less, and CN103641781A discloses a kind of naphthalene two formyl compounds and salt thereof as plant growth regulator, as agricultural produce upgrading. CN104920448A discloses a kind of naphthalimide phosphate kalium salt, has good plant growth and regulates activity.
In the prior art, there is a kind of aphthalimide base aryl urea compounds of higher bactericidal activity and cell division activity and being applied in as described in the present invention and be showed no open both at home and abroad.
Summary of the invention
It is an object of the invention to provide a kind of a kind of aphthalimide base aryl urea compounds having bactericidal activity and cell division activity concurrently, it can be used for crops and the preventing and treating of vegetable fungal disease as antibacterial, and it can be used for the increasing yield and improving quality of crops as basic element of cell division plant growth regulator.
Technical scheme is as follows: a kind of aphthalimide base aryl urea compounds, structure shown in formula I:
Compound of formula I can be prepared by following reaction equation:
1,8-naphthalic anhydride and hydrazine hydrate reaction production N-amino-1,8-naphthalimide (Compound II per);
Compound II per reacts production I with 3,5-dichloro carbanil.
The concrete preparation method of compound of formula I is shown in synthesis example.
Present invention additionally comprises compound of formula I as fungicidal activity component, it is possible to be used alone, it is also possible to use with other antibacterial and other active substance combination, in order to improve the comprehensive function of product. This microbicide compositions also includes acceptable carrier in agricultural or forestry.
Present invention additionally comprises the compound of formula I plant growth regulator composition as active component, in said composition, active component refers to the compositions of compound of formula I or compound of formula I and other active components such as one of plant growth regulator such as Nafusaku, compound sodium nitrophenolate, indolebutyric acid sodium, two or more composition, also includes acceptable carrier in agricultural or forestry in this plant growth regulator composition.
Advantages of the present invention and good effect:
Indoor and field control effectiveness test shows, agricultural Common fungi disease such as early blight of tomato, droop, the cercospora brown spot of peanut, ring rot of apple etc. are had excellent prevention effect by formula I, especially that Phytophthora capsici disease preventive effect is especially prominent. While preventing and treating fungal disease, crop can be played again growth promotion, increasing yield and improving quality and promote precocious effect. As for Fructus Vitis viniferae, under compound of formula I 200 �� g/mL concentration in the spray in 20 days of trophophase interval once, after spraying three times, fruit white rot of grape, rust preventive effect, up to more than 80%, precocious 6��7 days, increase production 28.1%, and the appearance color of fruit and mouthfeel have clear improvement. Respectively spraying once in soybean seedling phase and phase of blossoming and bearing fruit under 100 �� g/mL concentration, the preventive effect such as downy mildew, Semen sojae atricolor butt rot, grey speck of soybean reaches more than 85%, increases production 15.2%, precocious 4��5 days. Good diseases prevention and volume increase dual function is all had for other crop such as Semen arachidis hypogaeae, Semen Maydis, Semen Tritici aestivi etc. The preparation of formula I is simple, produce and use cost is low, not only disease prevention but also increase production, and input-output ratio is high, is multi-functional agrochemical product rare at present, has good commercialization and market potential.
Detailed description of the invention
Following synthesis example, formulation examples and raw result of the test of surveying can be used to further illustrate the present invention, but are not intended to limit the present invention.
Synthesis example
Example 1, compound of formula I synthesis
(1) preparation of Formula II compound (N-amino-1,8-naphthalimide)
Being separately added into 19.8g (0.1ml) 1,8-naphthalic anhydride and 50mL hydrazine hydrate in 250mL there-necked flask, reflux 3h. Naturally it is down to room temperature, sucking filtration, dries to obtain 20.6g crystal, yield 97.2%.
(2) preparation of compound of formula I
In 250mL there-necked flask, it is separately added into 10.6g (0.05mol) Formula II compound and 100mL ethyl acetate, drips 10.3g (0.055mol) 3,5-dichloro carbanil under stirring, be heated to reflux 3h. Naturally being down to room temperature, sucking filtration obtains crude product. Obtain sterling with recrystallisation from isopropanol, dry to obtain 17.4g light yellow crystal, yield 87.0%. Compound of formula I fusing point: > 300 DEG C.
1HNMR (500MHz, DMSO), �� (ppm): 7.195 (s, 1H, ArH), 7.569 (s, 2H, ArH), 7.926-7.957 (t, 2H, ArH), 8.552-8.586 (t, 4H, ArH), 9.240 (s, 1H, NH), 9.805 (s, 1H, NH).
Formulation examples
The preparation of example 2,8% compound of formula I suspending agent
Weigh 8g compound of formula I, 2g dispersant NNO (sodium methylene bis-naphthalene sulfonate), 3gSP-2728 respectively, 2.5g isopropanol, 3g ethylene glycol, 2g white carbon, 1g organosilicon breast defoamer is in 250mL beaker, add 78.5g water, stirring, grind 2h with sand mill, rotating speed is 3000 revs/min, detection granularity 3 ��m��4 ��m, obtains white mobility suspending agent.
Raw survey example
Example 3, bactericidal activity are tested
By a certain amount of medicament dissolution in appropriate DMF, then it is diluted to 50mg/L with emulsified water. Adopt in vitro Plating, for examination pathogen: tomato early blight bacterium (A.solani), cucumber fusarium axysporum (C.cucumerinum), peanut Cercospora bacteria (C.rachidicola), Botryosphaeria berengeriana f. sp (Botryosphariadothidea), phytophthora blight of pepper (PhytophthoracapsiciLeonian).
Adopt biomass growth rate algoscopy (myceliumgrowthratetest), detailed process is: aseptically respectively draws 1mL medicinal liquid and injects in culture dish, add 9mLPDA culture medium, making 50mg/L pastille flat board after shaking up, the flat board to add 1mL aquesterilisa does blank.Cut bacterium dish with the card punch of diameter 4mm along mycelia outer rim, move on pastille plate, process in triplicate every time. Culture dish is placed in (24 �� 1) DEG C constant incubator and cultivates, 72h " Invest, Then Investigate " bacterium dish everywhere extension diameter, average, compare the relative bacteriostasis rate of calculating with blank.
Preventive effect (%)=(blank colony diameter-process colony diameter)/(blank colony diameter-4) �� 100%
Determine target compound to tomato early blight bacterium (A.solani), cucumber fusarium axysporum (C.cucumerinum), peanut Cercospora bacteria (C.rachidicola), Botryosphaeria berengeriana f. sp (Botryosphariadothidea), phytophthora blight of pepper (PhytophthoracapsiciLeonian) five kinds of thalline bactericidal activity, test concentrations is 100 �� g/mL and 10 �� g/mL, and bacteriostasis rate effect is listed in table 1.
Table 1 compound of formula I bacteriostasis rate to 5 kinds of pathogenic bacterias under 100 �� g/mL and 10 �� g/mL
Can be seen that several pathogenic bacterias are had higher suppression ratio by compound of formula I from biologically active data, be used for controlling fungus damage.
Example 4, cucumber cotyledons augmentation test
It is that Tianjin grinds No. 4 for examination cucumber variety, sow after seed soaking in the enamel tray with cover filling 0.7% agar, it is placed under 26 DEG C of dark situations and cultivates 72h, the cotyledon of selected size uniformity is stand-by, sample preparation adopts the filter paper enzyme in phytohormone activity substance-measuring, sampling test concentration is 100 �� g/mL, 10 �� g/mL and 1 �� g/mL, and solvent is DMF.
Specific practice is: type I compound and diphenylcarbamide (4-PU) being prepared is 100 �� g/mL, 10 �� g/mL and 1 �� g/mL mother solution, take each mother solution 0.3mL more respectively and uniformly drip on the filter paper of �� 6cm, after solvent is air-dry in the culture dish of �� 6cm, respectively put into the filter paper 1 containing sample, add distilled water 3mL, cotyledon 10, is 100 �� g/mL, 10 �� g/mL and 1 �� g/mL process. With distilled water for comparison. It is placed in 26 DEG C, cultivates under 3000Lux light intensity environment, after 72h, measure every 10 slice, thin piece leaf fresh weights. Often processing 2 times and repeat, results averaged, result of the test is in Table 2.
Table 2 cucumber cotyledons expansion contrast test
It is significantly better than control compounds diphenylcarbamide from table 2 test data, formula I and salt pair cucumber cotyledons expansion activity thereof.
Example 5, field experiment
Growth selection gesture, the plant that fruitful branch fineness degree is suitable longan grape as test maternal plant, 7 days florescences, full-bloom stage, spend after within 15 days, respectively spray with the medicinal liquid of 1 �� g/mL, with clear water for comparison, gather after maturation and process and compare fruit ear and take 30 fruits at random in the middle part of each process fruit ear, measure Single seed weight, statistics Single seed weight and yield, measure soluble solid content with hand-held saccharous detector, and the results are shown in Table 3.
Table 3 grape quality test data
| Compound | Soluble solid content (%) | Average particle weight (g) | Average particle weightening finish (%) | Rate of growth (%) |
| Compound of formula I | 21.0 | 6.27 | 46.5% | 48% |
| Diphenylcarbamide | 18.4 | 5.14 | 20.1% | 28% |
| CK (clear water) | 15.6 | 4.28 | - | - |
By table 3 data it can be seen that compound of formula I is while promoting grape fruit to expand, increasing yield, moreover it is possible to improve Fructus Vitis viniferae sugar content.
To sum up data, it can be seen that the compound of the present invention is the plant growth regulator of a kind of excellent combination property.
Claims (4)
1. an aphthalimide base aryl urea compounds, structure shown in formula I:
��
2. the purposes of an aphthalimide base aryl urea compounds according to claim 1, it is characterised in that compound of formula I is used as antibacterial or plant growth regulator.
3. a microbicide compositions, containing the compound of formula I described in claim 1 as acceptable carrier in fungicidal activity component and agricultural or forestry.
4. a plant growth regulator composition, containing the compound of formula I described in claim 1 as acceptable carrier in Activities of Plant Growth Regulators component and agricultural or forestry.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610052863.2A CN105646347A (en) | 2016-01-26 | 2016-01-26 | Naphthalimide aryl urea compound and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610052863.2A CN105646347A (en) | 2016-01-26 | 2016-01-26 | Naphthalimide aryl urea compound and application thereof |
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| Publication Number | Publication Date |
|---|---|
| CN105646347A true CN105646347A (en) | 2016-06-08 |
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| CN201610052863.2A Pending CN105646347A (en) | 2016-01-26 | 2016-01-26 | Naphthalimide aryl urea compound and application thereof |
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| Country | Link |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106866530A (en) * | 2017-01-10 | 2017-06-20 | 青岛科技大学 | A kind of naphthalimide replaces 2,4 dichloro-cinnamic acid ethyl ester compounds and its application |
| CN113899721A (en) * | 2021-09-13 | 2022-01-07 | 中国特种设备检测研究院 | Fluorescent probe, fluorescent probe kit and method for detecting sulfate reducing bacteria |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4197111A (en) * | 1978-09-27 | 1980-04-08 | Stauffer Chemical Company | 1,8-Naphthalimides and herbicide antidotes |
| CN104926725A (en) * | 2015-03-26 | 2015-09-23 | 青岛科技大学 | Naphthalimide arylurea compound and use thereof |
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2016
- 2016-01-26 CN CN201610052863.2A patent/CN105646347A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4197111A (en) * | 1978-09-27 | 1980-04-08 | Stauffer Chemical Company | 1,8-Naphthalimides and herbicide antidotes |
| CN104926725A (en) * | 2015-03-26 | 2015-09-23 | 青岛科技大学 | Naphthalimide arylurea compound and use thereof |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106866530A (en) * | 2017-01-10 | 2017-06-20 | 青岛科技大学 | A kind of naphthalimide replaces 2,4 dichloro-cinnamic acid ethyl ester compounds and its application |
| CN113899721A (en) * | 2021-09-13 | 2022-01-07 | 中国特种设备检测研究院 | Fluorescent probe, fluorescent probe kit and method for detecting sulfate reducing bacteria |
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