CN106942239B - The formamide of azophenlyene 1 transforms application of the compound 18 3 in Sclerotinia sclerotiorum is suppressed - Google Patents
The formamide of azophenlyene 1 transforms application of the compound 18 3 in Sclerotinia sclerotiorum is suppressed Download PDFInfo
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- CN106942239B CN106942239B CN201710169172.5A CN201710169172A CN106942239B CN 106942239 B CN106942239 B CN 106942239B CN 201710169172 A CN201710169172 A CN 201710169172A CN 106942239 B CN106942239 B CN 106942239B
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- azophenlyene
- formamides
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- transformation
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- 241000221696 Sclerotinia sclerotiorum Species 0.000 title claims abstract description 34
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 title abstract description 12
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 title abstract 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 230000009466 transformation Effects 0.000 claims abstract description 27
- 230000002265 prevention Effects 0.000 claims abstract description 5
- JGCSKOVQDXEQHI-UHFFFAOYSA-N phenazine-1-carboxylic acid Chemical compound C1=CC=C2N=C3C(C(=O)O)=CC=CC3=NC2=C1 JGCSKOVQDXEQHI-UHFFFAOYSA-N 0.000 claims description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- 229920001429 chelating resin Polymers 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 claims description 3
- 239000003905 agrochemical Substances 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 229920005989 resin Polymers 0.000 claims description 3
- 239000011347 resin Substances 0.000 claims description 3
- KJPJJUOYVQHBOE-UHFFFAOYSA-N [B]OCC(F)(F)F Chemical compound [B]OCC(F)(F)F KJPJJUOYVQHBOE-UHFFFAOYSA-N 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 238000012986 modification Methods 0.000 abstract description 13
- 230000004048 modification Effects 0.000 abstract description 13
- 239000000575 pesticide Substances 0.000 abstract description 9
- 238000000034 method Methods 0.000 abstract description 7
- 230000005764 inhibitory process Effects 0.000 abstract description 5
- 150000002611 lead compounds Chemical class 0.000 abstract description 2
- 230000001629 suppression Effects 0.000 abstract description 2
- 239000003814 drug Substances 0.000 description 13
- 241000196324 Embryophyta Species 0.000 description 8
- 230000002401 inhibitory effect Effects 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000003948 formamides Chemical class 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 3
- 230000001408 fungistatic effect Effects 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241001558929 Sclerotium <basidiomycota> Species 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000036039 immunity Effects 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000001018 virulence Effects 0.000 description 2
- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- FSCWZHGZWWDELK-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-5-ethenyl-5-methyl-2,4-oxazolidinedione Chemical compound O=C1C(C)(C=C)OC(=O)N1C1=CC(Cl)=CC(Cl)=C1 FSCWZHGZWWDELK-UHFFFAOYSA-N 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- TWFZGCMQGLPBSX-UHFFFAOYSA-N Carbendazim Natural products C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 235000007926 Craterellus fallax Nutrition 0.000 description 1
- 240000007175 Datura inoxia Species 0.000 description 1
- 239000005759 Diethofencarb Substances 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 244000020551 Helianthus annuus Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000005867 Iprodione Substances 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- 235000003228 Lactuca sativa Nutrition 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 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 1
- YDHFLRAOGSLXBP-UHFFFAOYSA-N O=C(c1cccc2c1nc(cccc1)c1n2)NCCCCc1ccccc1 Chemical compound O=C(c1cccc2c1nc(cccc1)c1n2)NCCCCc1ccccc1 YDHFLRAOGSLXBP-UHFFFAOYSA-N 0.000 description 1
- 239000005820 Prochloraz Substances 0.000 description 1
- 241000221662 Sclerotinia Species 0.000 description 1
- 239000005839 Tebuconazole Substances 0.000 description 1
- 239000005842 Thiophanate-methyl Substances 0.000 description 1
- 240000006677 Vicia faba Species 0.000 description 1
- 235000010749 Vicia faba Nutrition 0.000 description 1
- 235000002098 Vicia faba var. major Nutrition 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- JYZIHLWOWKMNNX-UHFFFAOYSA-N benzimidazole Chemical compound C1=C[CH]C2=NC=NC2=C1 JYZIHLWOWKMNNX-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- JNPZQRQPIHJYNM-UHFFFAOYSA-N carbendazim Chemical compound C1=C[CH]C2=NC(NC(=O)OC)=NC2=C1 JNPZQRQPIHJYNM-UHFFFAOYSA-N 0.000 description 1
- 239000006013 carbendazim Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229940126678 chinese medicines Drugs 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000008056 dicarboxyimides Chemical class 0.000 description 1
- LNJNFVJKDJYTEU-UHFFFAOYSA-N diethofencarb Chemical compound CCOC1=CC=C(NC(=O)OC(C)C)C=C1OCC LNJNFVJKDJYTEU-UHFFFAOYSA-N 0.000 description 1
- -1 diethofencarb etc. Chemical class 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000008686 ergosterol biosynthesis Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 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 1
- 239000010977 jade Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 description 1
- QXJKBPAVAHBARF-BETUJISGSA-N procymidone Chemical compound O=C([C@]1(C)C[C@@]1(C1=O)C)N1C1=CC(Cl)=CC(Cl)=C1 QXJKBPAVAHBARF-BETUJISGSA-N 0.000 description 1
- 238000004080 punching Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical group COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- DIEXQJFSUBBIRP-UHFFFAOYSA-N tris(2,2,2-trifluoroethyl) borate Chemical compound FC(F)(F)COB(OCC(F)(F)F)OCC(F)(F)F DIEXQJFSUBBIRP-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
Classifications
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/46—Phenazines
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
A kind of application of the formamide of azophenlyene 1 transformation compound 18 3 in Sclerotinia sclerotiorum is suppressed, the formamide of azophenlyene 1 transformation compound 18 3 (structural formula is seen below) is to be obtained using the formamide of azophenlyene 1 as parent through structure of modification.The suppression that the present invention determines 18 3 pairs of Sclerotinia sclerotiorums of the transformation compound using growth rate method is used, and is as a result shown：The inhibition of 18 3 pairs of Sclerotinia sclerotiorums of transformation compound is good, and is better than the formamide of azophenlyene 1, shows that the transformation compound 18 3 can be as the lead compound of prevention and control sclerotinia sclerotiorum novel pesticide.
Description
Technical field
The invention belongs to pesticides discovery field, more particularly to azophenlyene -1- formamides transformation compound 18-3 is suppressing rape
Application in hyphal cluster germ (Sclerotinia sclerotiorum).
Background technology
Rape is the important oil crops in China, and seed oil content has higher economic value between 33-55%.Oil
Dish can not only be used for squeezing edible oil and feed, but also have been widely used in medicine, industry, food etc. tool.Most
Near result of study shows that China is that rapeseed cultivation big country, its area are about 7,000,000 hectares in the world, is important rape life
Produce state.Rape growth cycle length, often disturbed by various factors, wherein sclerotinia sclerotiorum be influence rape yield increasing it is important because
Element.The disease is also known as stem rot, the mould root and stem of certain plants, white stalk, empty stalk etc., is a kind of fungal disease as caused by sclerotinite, can parasitize
The various plants of section more than 70 400.The sick host can also colonize in peanut, broad bean, sunflower, lettuce in addition to crucifer
Deng on crop.The presence of sclerotium is to cause the primary source of infection of sclerotinia sclerotiorum.Caused ascospore is in air after sclerotial germination
Middle propagation, ascospore is typically fallen on the petal of plant first infects petal, then falls on plant by the petal of bacteria infection
Plant is infected on the cauline leaf of strain.The sick generation can cause rape mass of 1000 kernel to reduce, silique is reduced, seed wrinkle is flat, plant is early withered
Deng causing rape underproduction 10%-50%, or even up to 80%, to bringing massive losses in production.
The method that sclerotinia sclerotiorum is prevented and treated in production relies primarily on chemical prevention, the chemistry available for control sclerotinia sclerotiorum
Agricultural chemicals has ergosterol biosynthesis inhibitor class such as prochloraz, Tebuconazole；Benzimidazole such as carbendazim, thiophanate methyl；
Substituted benzene such as Bravo；Dicarboximide class such as dimethachlon, procymidone, iprodione, vinclozolin；Triazole type such as the third ring
Azoles；Carbamates such as diethofencarb etc., but long-term a large amount of single use chemical pesticides, not only pollute environment, it is flat to destroy ecology
Weighing apparatus, and be also easy to cause germ to develop immunity to drugs.Therefore, the novel pesticide for seeking preventing and treating sclerotinia sclerotiorum is very urgent.
At present, developing the approach of novel pesticide mainly has chemical synthesis, the structure of modification of existing compound, from plant or micro- life
Novel compound of screening structure etc. in object, wherein the structure of modification of compound is the method for developing novel pesticide, not only
R＆D costs can be saved, and short-term benefit is notable.Azophenlyene -1- the formamides with bacteriostasis were once studied by this seminar,
But its bacteriostasis is limited, therefore, this seminar using azophenlyene -1- formamides as parent, by structure of modification and obtain azophenlyene -
1- formamides transformation compound 18-3.For the potentiality to be exploited of the clearly modification, this research evaluation its to Sclerotinia sclerotiorum
Inhibition and synergistic effect, it is intended to the novel pesticide of horn of plenty preventing and treating sclerotinia sclerotiorum provides theoretical foundation and practical basis.
The content of the invention
The technical problem to be solved by the invention is to provide a kind of azophenlyene -1- formamides transformation compound 18-3 to suppress
Application in Sclerotinia sclerotiorum, the azophenlyene -1- formamides transformation compound 18-3 be using azophenlyene -1- formamides be parent through tie
Structure transformation obtains, and the present invention also determines the suppressions of the transformation compound 18-3 to Sclerotinia sclerotiorum using mycelial growth rate method
Effect processed, the results showed that the transformation compound 18-3 is good to the inhibition of Sclerotinia sclerotiorum, and is better than azophenlyene -1- formyls
Amine.
In order to solve the above technical problems, the technical solution adopted in the present invention is：A kind of azophenlyene -1- formamides transform chemical combination
Applications of the thing 18-3 in Sclerotinia sclerotiorum is suppressed.
Present invention simultaneously provides a kind of azophenlyene -1- formamides transformation compound 18-3 to prepare prevention and control sclerotinia sclerotiorum agricultural chemicals
In application.
Above-mentioned azophenlyene -1- formamides transformation compound 18-3 structural formula is as follows：
Above-mentioned azophenlyene -1- formamides transformation compound 18-3 is using azophenlyene -1- formamides as parent, by azophenlyene -1- formyls
Amine hydrolyzes generation phenazine-1-carboxylic acid in acid condition, and 4- phenyibutylamines, three (trifluoroethoxies are added in phenazine-1-carboxylic acid
Base) boron and acetonitrile reacted, and DCM and water are added after reaction solution cooling, sequentially add Amberlyst A-26 (OH),
Amberlyst 15, Amberlite IRA743 resins, react under room temperature condition and obtain.
Compared with prior art, the present invention have the advantage that for：This transformation compound 18-3 has to Sclerotinia sclerotiorum
Stronger virulence, its EC50For 4.25 μ g/mL, than the EC of comparison medicament azophenlyene -1- formamides50It is low；This transformation compound 18-3
There is preferable inhibition to Sclerotinia sclerotiorum, and inhibition is better than azophenlyene -1- formamides, this transformation compound 18-3
It is not easy to make germ develop immunity to drugs, enriches the novel pesticide of preventing and treating Sclerotinia sclerotiorum.
Brief description of the drawings
Fig. 1 is the azophenlyene -1- formamides transformation compound 18-3 of present invention mass spectrogram.
Embodiment
Technical scheme is described further with reference to specific experiment and embodiment, present invention experiment and real
It is mass percent to apply the percentage being related in example.
Azophenlyene -1- the formamides of embodiment 1 transformation compound 18-3 preparation
Transform compound 18-3 synthesis：Azophenlyene -1- formamides are hydrolyzed into generation phenazine-1-carboxylic acid in acid condition；
Take 6.2mmol phenazine-1-carboxylic acids (1.4179g), 6.2mmol 4- phenyibutylamines (1ml), 12.4mmol tri- (trifluoro ethoxy)
Boron (2.675ml) and 12.4ml acetonitriles are added in 25ml round-bottomed flasks, magnetic agitation, 80 DEG C of reaction 24h, after reaction solution cooling
20ml DCM and 3ml water is added, sequentially adds Amberlyst A-26 (OH), Amberlyst 15, Amberlite
Each 930mg of IRA743 resins, 30min is stirred under room temperature condition, then add the water removal of anhydrous slufuric acid magnesium dust, filtering, using dry
Dry DCM washs solid magnesium sulfate 3 times, revolving, must transform compound 18-3, yield 52.64%.
Azophenlyene -1- the formamides of embodiment 2 transformation chemical combination 8-3 Structural Identification
Compose through hydrogen (1H NMR (500MHz, CDCl3) δ 11.04 (s, 54H), 9.05-8.86 (m, 56H), 8.52-7.66
(m, 363H), 7.29 (s, 10H), 7.33-7.14 (m, 15H), 4.03-3.44 (m, 255H), 3.41 (d, J=3.3Hz,
163H), 3.35 (t, J=4.6Hz, 13H), 2.67 (s, 4H), 2.33 (d, J=13.9Hz, 4H), 2.18-2.01 (m, 122H),
1.83 (dd, J=12.6,6.1Hz, 4H), 1.48-1.14 (m, 107H), 1.74-0.78 (m, 275H), 1.53-0.78 (m,
253H), 1.00 (ddd, J=18.6,14.5,7.3Hz, 26H), 0.93-0.50 (m, 119H) ,-0.00 (s, 14H)), carbon spectrum
(13C NMR(126MHz,CDCl3)δ164.77(s),143.41(s),142.91(s),141.33(s),140.84(s),
135.35(s),133.52(s),131.60(s),131.00(s),130.09(s),129.69(s),129.21(s),129.02
(s), 77.32 (s), 77.07 (s), 76.81 (s), 70.94 (s), 58.80 (s), 37.46 (s), 29.52 (s)) and mass spectrum (point
Son amount：355.17, Fig. 1) detect the compound synthesized in above-described embodiment to coincide with target, its molecular formula is C23H21N3O,
Structural formula is as follows：
Azophenlyene -1- the formamides of embodiment 3 transform determinations of activity of the chemical combination 18-3 to Sclerotinia sclerotiorum
(1) instrument and associated materials
YJ-VS-2 types superclean bench (the net cleaning equipment Co., Ltd in Wuxi one), LDZX-30E autoclaves (are pacified Shanghai Shen
Medical apparatus and instruments factory), MPJ-250 types incubator (Shanghai gloomy reliable test Instrument Ltd.), QHX-400B-III type illumination cultivations
Case (Shanghai new talent medicine equipment Manufacturing Co., Ltd), electric furnace (Beijing Zhong Xing great achievements Instrument Ltd.) etc. and graduated cylinder, glass
Glass rod, beaker, triangular flask, ruler, pencil, label paper, sealed membrane, choose pin, volumetric flask, transfer needle, ph-101 watering cans, punching
Device, culture dish, kitchen knife, gauze.
(2) medicament
Azophenlyene -1- formamides transformation compound 18-3 active compounds (hereinafter referred to as modification 18-3) made from embodiment 1；Fine jade
The medicaments such as fat, glucose, acetone and Tween 80 are bought from Chinese medicines group.
(3) bacterial strain
Experiment is big by Agriculture in Hunan with the Sclerotinia sclerotiorum (Sclerotinia sclerotiorum) of wild responsive type
Learn the separation of plant pathology laboratory, identification and preserve.
(4) determinations of activity of the modification 18-3 to Sclerotinia sclerotiorum
Modification 18-3 is determined to Sclerotinia sclerotiorum (Sclerotinia sclerotiorum) using growth rate method
Bacteriostasis.Take proper amount of acetone to dissolve modification 18-3 active compounds, be then configured to the mother that mass concentration is 1000 μ g/mL
Liquid, by decoction and culture medium 1：9 volume ratio is configured to the drug containing flat board that final content of dispersion is 2.5,5,10,20,40 μ g/mL,
Beaten with diameter 5mm card punch in preculture 2d Sclerotinia sclerotiorum colony edge and take bacteria cake face down to be inoculated into drug containing to put down
On plate, often processing is repeated 3 times, and to make blank control without medicine flat board, is placed in 26-28 DEG C of incubator, colony diameter length to be compareed
During to 2/3 entirely cultivated, the colony diameter of each processing is measured using crossing method.Meanwhile tested using same method
Inhibitory action of the azophenlyene -1- formamides to rape sclerotium.Calculate inhibiting rate, EC50Value, coefficient correlation and regression equation, are as a result shown in
Table 1 below and table 2.
(5) result and analysis
As shown in Table 1, modification 18-3 concentration is higher, and fungistatic effect is better.When modification 18-3 concentration is 40 μ g/mL
When, fungistatic effect is best, and its inhibiting rate is 81.40%；Secondly, when modification 18-3 concentration is 20 μ g/mL, fungistatic effect
It；The inhibiting rate of other processing is less than 60%.The medicament has compared with strong virus force effect (EC to Sclerotinia sclerotiorum50For 10.52 μ
G/mL, regression equation Y=1.6102x+3.3545, coefficient correlation 0.9884), its virulence is better than comparison medicament azophenlyene -1-
Formamide (EC50For 14.31 μ g/mL, regression equation Y=1.2266x+3.6858, coefficient correlation 0.9132), show originally to change
Divine force that created the universe 18-3 can be as the lead compound of prevention and control sclerotinia sclerotiorum novel pesticide.
Inhibitory action of the azophenlyene -1- formamide modification 18-3 of table 1 to Sclerotinia sclerotiorum
Inhibitory action of the azophenlyene -1- formamides (comparison medicament) of table 2 to Sclerotinia sclerotiorum
Claims (3)
1. a kind of applications of azophenlyene -1- formamides transformation compound 18-3 in Sclerotinia sclerotiorum is suppressed, the azophenlyene -1- formyls
Amine transformation compound 18-3 structural formula is as follows：
2. a kind of applications of azophenlyene -1- formamides transformation compound 18-3 in prevention and control sclerotinia sclerotiorum agricultural chemicals is prepared, the azophenlyene -
1- formamides transformation compound 18-3 structural formula is as follows：
3. application as claimed in claim 1 or 2, it is characterised in that the azophenlyene -1- formamides transformation compound 18-3 be with
Azophenlyene -1- formamides are parent, azophenlyene -1- formamides are hydrolyzed into generation phenazine-1-carboxylic acid in acid condition, in azophenlyene -1-
4- phenyibutylamines, three (trifluoro ethoxy) boron and acetonitrile are added in carboxylic acid to be reacted, and DCM and water are added after reaction solution cooling,
Amberlyst A-26 (OH), Amberlyst 15, Amberlite IRA743 resins are sequentially added, is reacted under room temperature condition
Obtain.
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