CN104529900A - Bactericidal activity of 1-substituted-N-substituted phenyl-5-amidogen-1H-pyrazole-4-formamide compound - Google Patents
Bactericidal activity of 1-substituted-N-substituted phenyl-5-amidogen-1H-pyrazole-4-formamide compound Download PDFInfo
- Publication number
- CN104529900A CN104529900A CN201410852814.8A CN201410852814A CN104529900A CN 104529900 A CN104529900 A CN 104529900A CN 201410852814 A CN201410852814 A CN 201410852814A CN 104529900 A CN104529900 A CN 104529900A
- Authority
- CN
- China
- Prior art keywords
- substituted
- pyrazole
- substituted phenyl
- bactericidal activity
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 10
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 title abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 19
- -1 phenyl-5-amino-1H-pyrazole-4-formamide compound Chemical class 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- UBKSUPKIDNXMMC-UHFFFAOYSA-N 5-amino-1-phenylpyrazole-4-carboxamide Chemical class NC1=C(C(=O)N)C=NN1C1=CC=CC=C1 UBKSUPKIDNXMMC-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 2
- 125000005336 allyloxy group Chemical group 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 125000005291 haloalkenyloxy group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000005605 benzo group Chemical group 0.000 abstract 1
- 239000012141 concentrate Substances 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 0 *c(c(*)c1)cc(NC(c2c(N)[n](*)nc2)=O)c1F Chemical compound *c(c(*)c1)cc(NC(c2c(N)[n](*)nc2)=O)c1F 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 241000221785 Erysiphales Species 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 230000000855 fungicidal effect Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- NVRCXLPKLCKSSN-UHFFFAOYSA-N 5-amino-1-methylpyrazole-4-carboxylic acid Chemical compound CN1N=CC(C(O)=O)=C1N NVRCXLPKLCKSSN-UHFFFAOYSA-N 0.000 description 4
- 240000008067 Cucumis sativus Species 0.000 description 4
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 240000005979 Hordeum vulgare Species 0.000 description 3
- 235000007340 Hordeum vulgare Nutrition 0.000 description 3
- 240000007594 Oryza sativa Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 206010039509 Scab Diseases 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000221662 Sclerotinia Species 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 244000052616 bacterial pathogen Species 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PFFIDZXUXFLSSR-UHFFFAOYSA-N 1-methyl-N-[2-(4-methylpentan-2-yl)-3-thienyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound S1C=CC(NC(=O)C=2C(=NN(C)C=2)C(F)(F)F)=C1C(C)CC(C)C PFFIDZXUXFLSSR-UHFFFAOYSA-N 0.000 description 1
- BNYCHCAYYYRJSH-UHFFFAOYSA-N 1h-pyrazole-5-carboxamide Chemical class NC(=O)C1=CC=NN1 BNYCHCAYYYRJSH-UHFFFAOYSA-N 0.000 description 1
- 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
- NRTLIYOWLVMQBO-UHFFFAOYSA-N 5-chloro-1,3-dimethyl-N-(1,1,3-trimethyl-1,3-dihydro-2-benzofuran-4-yl)pyrazole-4-carboxamide Chemical compound C=12C(C)OC(C)(C)C2=CC=CC=1NC(=O)C=1C(C)=NN(C)C=1Cl NRTLIYOWLVMQBO-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
- 241000894006 Bacteria Species 0.000 description 1
- 241000221198 Basidiomycota Species 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- 235000002566 Capsicum Nutrition 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- 241001422926 Mayetiola hordei Species 0.000 description 1
- 206010027146 Melanoderma Diseases 0.000 description 1
- 239000005816 Penthiopyrad Substances 0.000 description 1
- 239000006002 Pepper Substances 0.000 description 1
- 241000233679 Peronosporaceae Species 0.000 description 1
- 241000233616 Phytophthora capsici Species 0.000 description 1
- 241000233622 Phytophthora infestans Species 0.000 description 1
- 235000016761 Piper aduncum Nutrition 0.000 description 1
- 235000017804 Piper guineense Nutrition 0.000 description 1
- 244000203593 Piper nigrum Species 0.000 description 1
- 235000008184 Piper nigrum Nutrition 0.000 description 1
- 241000500437 Plutella xylostella Species 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 241000221696 Sclerotinia sclerotiorum Species 0.000 description 1
- 241001558929 Sclerotium <basidiomycota> Species 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000012822 chemical development Methods 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- MEUSJJFWVKBUFP-UHFFFAOYSA-N ethyl 5-amino-1-methylpyrazole-4-carboxylate Chemical compound CCOC(=O)C=1C=NN(C)C=1N MEUSJJFWVKBUFP-UHFFFAOYSA-N 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention relates to bactericidal activity of a 1-substituted-N-substituted phenyl-5-amidogen-1H-pyrazole-4-formamide compound, wherein R1 represents alkyl, substituted phenyl and the like, X1 represents halogen, X2 represents an alkoxy group, an ene oxygen group, an alkyne oxygen group, a halogenated ene oxygen group and the like, and X1 and X2 can form a benzo 6-element heterocyclic ring with a benzene ring. The 1-substituted-N-substituted phenyl-5-amidogen-1H-pyrazole-4-formamide compound shows the bactericidal activity at the testing concentrate.
Description
[ technical field ]: the invention relates to bactericidal activity of 1-substituted-N-substituted phenyl-5-amino-1H-pyrazole-4-formamide compounds.
[ background Art ] A method of: the pyrazole carboxamide compound contains two high-activity structural groups of pyrazole and amide and has wide biological activity. Since the 40 s of the 20 th century, biologically active pyrazolecarboxamide derivatives including insecticides, acaricides, fungicides and herbicides have been reported in the field of agricultural chemical development.
Furametpyr (a) developed by sumitomo chemical company of japan in 1996 has a specific effect on most of germs of basidiomycetes, such as rice sheath blight disease, various rice sclerotinia diseases, and thread-whitening disease.
At the british plant protection conference of 2003, new amide fungicide penthiopyrad (B) is introduced by mitsui chemical corporation of japan, which has a broad fungicidal spectrum and shows excellent activity against rust and sclerotinia.
US 6054473 discloses a class of compounds C having fungicidal activity at 250g/hm2Is applied to barley white powder and 125g/hm2The control effect on barley sclerotium is 100 percent and 100g/hm2The effective rate of the pesticide on apple scab is 91 percent at 100g/hm2The inhibition rate of the powdery mildew on cucumber is 100%.
JP 2004189738 discloses that compound D has a killing rate of more than 90% against cabbage diamondback moth at a concentration of 500 mg/L.
WO 03010149 discloses Compound E at 250mg/L against M.hordei, 100g/hm2The control effect on apple powdery mildew can reach 100 percent.
WO 03070705 discloses a class of compounds F at 100g/hm2Can completely inhibit apple powdery mildew, cucumber powdery mildew, apple scab and tomato black spot, can be used for preventing and treating powdery mildew, rust disease, downy mildew and other diseases, and especially has good treatment and protection effects on barley net blotch and apple powdery mildew.
[ summary of the invention ]: the invention aims to provide a 1-substituted-N-substituted phenyl-5-amino-1H-pyrazole-4-formamide compound with bactericidal activity. The compounds are different from the reported compounds and have novel structures.
The compounds of the invention have the general formula (I):
in the formula,
R1alkyl, substituted phenyl, etc.;
X1is halogen;
X2alkoxy, alkenyloxy, alkynyloxy, haloalkenyloxy, etc.;
X1and X2Can also form a benzo 6-membered heterocyclic ring with a benzene ring, and the general formula is (II);
wherein,
r is alkyl, alkenyl or alkynyl;
said alkyl group being C1～C6Is straight-chain or branched alkyl, alkenyl isAlkenyl or alkynyl of (A) is C3～C6Alkynyl group of (1).
The compound is characterized in that:
R1preferably methyl, n-propyl, phenyl, m-trifluoromethylphenyl;
X1preferably chlorine;
X2preferably methoxycarbonyloxy, ethoxycarbonyloxy, isopropyloxy, allyloxy, propargyloxy, cyclopentyloxy, isopentyloxy;
X1and X2And can form a benzo 6-membered heterocyclic ring with a benzene ring, which has the general formula (II), wherein R is preferably n-propyl, allyl, propargyl or ethoxycarbonylmethyl.
The 1-substituted-N-substituted phenyl-5-amino-1H-pyrazole-4-formamide compound can be prepared by the following method: dissolving a compound (a) in a solvent, adding an inorganic base, heating to 40-80 ℃, hydrolyzing to obtain a compound (b), performing thionyl chloride chlorination on the compound (b) to obtain a compound (c), and reacting with the compound (d) to obtain a 1-substituted-N-substituted phenyl-5-amino-1H-pyrazole-4-formamide compound (I). The solvent is as follows: toluene, benzene, acetonitrile, tetrahydrofuran, dioxane, methanol, ethanol, water, or a mixed solvent of the above solvents in any proportion; the inorganic base is sodium hydroxide or potassium hydroxide.
The invention is further illustrated by the compounds listed in Table 1, but is not limited thereto.
The 1-substituted-N-substituted phenyl-5-amino-1H-pyrazole-4-formamide compound provided by the invention is different from the known compounds, has a completely novel structure and has better bactericidal activity.
The compound of the invention is applied to pesticides as a bactericide.
[ embodiments ] of the present invention:
the invention is further illustrated by the following examples in which the melting points are uncorrected.
Example 1: synthesis of 1-methyl-5-amino-1H-pyrazole-4-carboxylic acid (b1)
In a 500mL round bottom flask, 8.45g of ethyl 1-methyl-5-amino-1H-pyrazole-4-carboxylate (a1), 50mL of tetrahydrofuran, 50mL of anhydrous methanol and 50mL of 2.5mol/L aqueous sodium hydroxide solution were added, the mixture was heated to 60 ℃, the temperature was controlled for 4 hours, most of the solvent was removed under reduced pressure, the residue was acidified to pH 1 with 6mol/L hydrochloric acid, a milky precipitate appeared, filtered, washed with water and dichloromethane, respectively, and dried to give b1(5.55g) as a white solid, in 78.7% yield, melting point 67-68 ℃.
Example 2: synthesis of 1-methyl-5-amino-1H-pyrazole-4-carbonyl chloride (c1)
0.71g of 1-methyl-5-amino-1H-pyrazole-4-carboxylic acid (b1) is added into a 50mL round-bottom flask, 10mL of thionyl chloride is added dropwise under cooling of an ice salt bath, the mixture is naturally raised to room temperature after being added dropwise, the mixture is stirred for 3 hours, the thionyl chloride is pumped out under reduced pressure to obtain yellow solid c1(0.98g), the reaction is quantitatively finished, and the melting point is 128-130 ℃.
Example 3: synthesis of 1-methyl-5-amino-N- (2-fluoro-4-chloro-5-allyloxypropyl) -1H-pyrazole-4-carboxamide (I4)
Adding 0.40g of 2-fluoro-4-chloro-5-allyloxyaniline, 10mL of dichloromethane and 1mL of pyridine into a 50mL round-bottom flask, cooling a ice salt bath to below 0 ℃, adding 0.39g of 1-methyl-5-amino-1H-pyrazole-4-formyl chloride (c1), naturally raising the temperature to room temperature, detecting the reaction by TLC, removing the solvent under reduced pressure after the reaction is finished, washing a residual solution by 30mL of 1mol/L hydrochloric acid, filtering, washing a solid by a saturated sodium bicarbonate solution, filtering, and drying to obtain an off-white solid I4(0.52g), wherein the yield is 80.1 percent, and the melting point is 184-.
Similarly, other compounds of the invention can be synthesized in a similar manner, as shown in Table 1.
TABLE 1 characterization of physical Properties of Compound I
Example 4: fungicidal Activity test
A certain amount of the medicament is dissolved in a proper amount of DMF and then diluted to 50mg/L by using emulsified water. The results obtained by the ex vivo plate method are shown in Table 2. Pathogenic bacteria to be tested: cucumber fusarium wilt, peanut brown spot, apple ring rot, tomato early blight, wheat scab, potato late blight, sclerotinia sclerotiorum, cucumber gray mold, rice sheath blight and pepper phytophthora capsici.
A cell growth rate assay (mycelium growth rate test) was used. The specific process is as follows: under the aseptic condition, 1mL of liquid medicine is respectively sucked and injected into a culture dish, 9mL of PDA culture medium is added, a 50mg/L medicine-containing plate is prepared after shaking up, and a plate added with 1mL of sterilized water is used as a blank control. The plate was cut along the outer edge of the hyphae with a 4mm diameter punch and transferred to a drug-containing plate, and the treatment was repeated three times each time. The culture dish is placed in a constant temperature incubator at 24 +/-1 ℃ for culture. And (5) investigating the expansion diameter of each treated bacterium disc after 72h, calculating an average value, and comparing with a blank control to calculate the relative bacteriostasis rate. A: more than or equal to 50 percent; b: not less than 20 percent; c: less than 20%.
Table 2: inhibitory Rate (%) of fungicidal Activity of Compound I (concentration 50mg/L)
Claims (3)
1. A1-substituted-N-substituted phenyl-5-amino-1H-pyrazole-4-formamide compound with bactericidal activity is characterized by having a structure shown in the following general formula (I):
in the formula,
R1alkyl, substituted phenyl, etc.;
X1is halogen;
X2alkoxy, alkenyloxy, alkynyloxy, haloalkenyloxy, etc.;
X1and X2Can also form a benzo 6-membered heterocyclic ring with a benzene ring, and the general formula is (II);
wherein,
r is alkyl, alkenyl or alkynyl;
said alkyl group being C1～C6Is straight-chain or branched alkyl, alkenyl is C 3 ～C6Alkenyl or alkynyl of (A) is C3～C6Alkynyl group of (1).
2. The compound of claim 1, wherein:
R1preferably methyl, n-propyl, phenyl, m-trifluoromethylphenyl;
X1preferably chlorine;
X2preferably methoxycarbonyloxy, ethoxycarbonyloxy, isopropyloxy, allyloxy, propargyloxy, cyclopentyloxy, isopentyloxy;
X1and X2And can form a benzo 6-membered heterocyclic ring with a benzene ring, which has the general formula (II), wherein R is preferably n-propyl, allyl, propargyl or ethoxycarbonylmethyl.
3. Use of 1-substituted-N-substituted phenyl-5-amino-1H-pyrazole-4-carboxamides according to claim 1, characterized by bactericidal activity.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410852814.8A CN104529900A (en) | 2014-12-31 | 2014-12-31 | Bactericidal activity of 1-substituted-N-substituted phenyl-5-amidogen-1H-pyrazole-4-formamide compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410852814.8A CN104529900A (en) | 2014-12-31 | 2014-12-31 | Bactericidal activity of 1-substituted-N-substituted phenyl-5-amidogen-1H-pyrazole-4-formamide compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN104529900A true CN104529900A (en) | 2015-04-22 |
Family
ID=52845580
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410852814.8A Pending CN104529900A (en) | 2014-12-31 | 2014-12-31 | Bactericidal activity of 1-substituted-N-substituted phenyl-5-amidogen-1H-pyrazole-4-formamide compound |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104529900A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108484614A (en) * | 2018-05-23 | 2018-09-04 | 南开大学 | Pyrazolo [3,4-d] pyrimidine -4 (5H) -one derivative and its preparation method and application |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996016954A1 (en) * | 1994-12-02 | 1996-06-06 | Agrevo Uk Limited | Derivatives of anthranilic acid useful as fungicides |
| CN1533380A (en) * | 2001-07-25 | 2004-09-29 | �ݶ�ũ�����ѧ�ɷݹ�˾ | N-pyrazolylcarboxanilides as fungicides |
| CN1646494A (en) * | 2002-02-19 | 2005-07-27 | 拜尔农作物科学股份公司 | Disubstituted pyrazolyl carboxanilides |
| CN101215289A (en) * | 2008-01-11 | 2008-07-09 | 南开大学 | 3-substituted phenyl-pyrazolo[3,4-d][1,2,3]triazin-4-one compounds with PPO restraining activity and weeding activity |
| CN105017258A (en) * | 2014-12-30 | 2015-11-04 | 南开大学 | Prepartion and application of pyrazolo[3,4-d][1,2,3]triazine-4-one derivative |
-
2014
- 2014-12-31 CN CN201410852814.8A patent/CN104529900A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996016954A1 (en) * | 1994-12-02 | 1996-06-06 | Agrevo Uk Limited | Derivatives of anthranilic acid useful as fungicides |
| CN1533380A (en) * | 2001-07-25 | 2004-09-29 | �ݶ�ũ�����ѧ�ɷݹ�˾ | N-pyrazolylcarboxanilides as fungicides |
| CN1646494A (en) * | 2002-02-19 | 2005-07-27 | 拜尔农作物科学股份公司 | Disubstituted pyrazolyl carboxanilides |
| CN101215289A (en) * | 2008-01-11 | 2008-07-09 | 南开大学 | 3-substituted phenyl-pyrazolo[3,4-d][1,2,3]triazin-4-one compounds with PPO restraining activity and weeding activity |
| CN105017258A (en) * | 2014-12-30 | 2015-11-04 | 南开大学 | Prepartion and application of pyrazolo[3,4-d][1,2,3]triazine-4-one derivative |
Non-Patent Citations (1)
| Title |
|---|
| 李华斌等: "3-(2-氟-4-氯-5-取代基苯基)-7-甲基-3H-吡唑并[3,4-d][1,2,3]三嗪-4(7H)-酮化合物的合成及其对原卟啉原氧化酶的抑制活性", 《有机化学》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108484614A (en) * | 2018-05-23 | 2018-09-04 | 南开大学 | Pyrazolo [3,4-d] pyrimidine -4 (5H) -one derivative and its preparation method and application |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US7714140B2 (en) | 1,2 Benzoisothiazole derivative, and agricultural or horticultural plant disease- controlling agent | |
| JP5122293B2 (en) | Thieno-pyrimidine compounds having fungicidal activity | |
| CN104163791B (en) | N-pyridine (hetero) aryl amide compound and preparation method and application thereof | |
| BRPI0617171A2 (en) | thiazole compounds, process for their production and use, agent for combating undesirable microorganisms, process for said combat, process for producing combat agents and intermediate products | |
| PL168441B1 (en) | Pesticide | |
| RU2194040C2 (en) | Derivatives of pyrimidinylhydroxyalkaneamides and fungicides for agriculture or gardening | |
| US4663327A (en) | 1-heteroaryl-4-aryl-pyrazolin-5-ones | |
| JPS6147403A (en) | Method of repelling plant pathoginic fungi by use of fungicidal composition containing n-acetonylbenzamide | |
| JPH0381259A (en) | S-(beta-dicarbonyl)substituted b-thioacrylamide biocide and disinfectant | |
| CN111362932A (en) | Isothiazole oxadiazole amide derivatives and preparation method and application thereof | |
| CN111285814B (en) | Quinazolinone compound containing hydrazone structural unit or stereoisomer thereof, or salt or solvate thereof | |
| Tang et al. | Morpholine derivatives in agrochemical discovery and development | |
| US5102898A (en) | Benzoxazolone compounds and the use thereof as microbicides | |
| CN109476606B (en) | Benzosultams and analogs and their use as fungicides | |
| KR20010031064A (en) | Oxyranyle-triazoline thiones and their use as microbicides | |
| CN108059614B (en) | Pyrazole amide compound and application thereof | |
| CN104529900A (en) | Bactericidal activity of 1-substituted-N-substituted phenyl-5-amidogen-1H-pyrazole-4-formamide compound | |
| CZ307295A3 (en) | S-oxides of benzothiephenecarbocylic acid amide, process of their preparation, their use and microbicidal preparation containing said compounds | |
| EP0816363B1 (en) | 1,2,3-Benzothiadiazole derivatives and their use as microbicides | |
| CN105712973B (en) | A kind of pyrazol acid amide compounds and its application | |
| CN111662282B (en) | Aza-and pyridine compounds and intermediates thereof | |
| JPH0248572A (en) | Novel thiazole compound, its production and sterilizing composition containing said compound as effective component | |
| KR19990036243A (en) | Halobenzimidazole and their use as a microbicide | |
| JP2003518099A (en) | Pyrazolylbenzyl ether derivatives with fluoromethoxy groups and their use as pesticides | |
| CN108117518A (en) | N-2,4- substituted-phenyl bisamide class compounds and preparation method and application |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20150422 |
|
| WD01 | Invention patent application deemed withdrawn after publication |