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CN105949179A - Furan-containing pyrimidine dipyrazole formamide derivatives, and preparation method and application thereof - Google Patents

Furan-containing pyrimidine dipyrazole formamide derivatives, and preparation method and application thereof Download PDF

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Publication number
CN105949179A
CN105949179A CN201610522817.4A CN201610522817A CN105949179A CN 105949179 A CN105949179 A CN 105949179A CN 201610522817 A CN201610522817 A CN 201610522817A CN 105949179 A CN105949179 A CN 105949179A
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herba
fructus
huo
agent
semen
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霍静倩
张金林
赵斌
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Heibei Agricultural University
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Heibei Agricultural University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • 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
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth 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)

Abstract

The invention provides a furan-containing pyrimidine dipyrazole formamide derivative, a preparation method and application thereof, and relates toThe pyrimidine dipyrazole formamide derivatives containing furan have a chemical structural general formula shown as V.

Description

One class pyrimidine connection pyrazolecarboxamide analog derivative containing furan and its production and use
Technical field
Technical scheme relates to the amide derivatives of amide bond, is specifically related to the pyrimidine connection pyrazolecarboxamide analog derivative containing furan.
Background technology
Pesticide, at preventing and treating crop diseases and pest crop smothering, improves agricultural output and quality aspect plays an important role.In the past few decades, chemical pesticide has played an important effect in agricultural development.But, along with the long-term, continuous of chemical pesticide and large area use, the resistance problem of agricultural pest is increasingly severe.It addition, chemical pesticide the most increasingly causes the attention of the mankind to the impact that environment and human health produce.Therefore, research and development high activity, low usage amount, environmentally friendly pesticide are extremely urgent.
At present, the hot fields of New pesticides discovery is to excavate and obtain low-residual, high selective environment friendly agricultural from natural product, is then changed into after structure optimization and can become the product entering pesticide market.With natural product as lead compound, the novel pesticide developing synthesis after structural modification, transformation occupies increasingly consequence in pesticide market.In addition, in target organism life process, the Physiology and biochemistry mechanism of action of certain key is as study model, the artificial compound designing this mechanism of action of cumulative interference, therefrom filters out lead compound, then carrying out structure optimization, exploitation novel agrochemical is also an important channel of New pesticides discovery.
This seminar early stage carries out computer medicine virtual screening with transketolase for target and has obtained the preferable amides compound of a kind of activity, and it can be as the lead compound of novel pesticide research.The present invention is with this compound as lead compound, difference is had the group of pesticide activity and introduces in this compound by the principle utilizing pesticide molecule to design, design has synthesized the amide derivatives of a class amide bond, and carried out the bioactivity screening of system, provide more efficient candidate compounds to the initiative for novel pesticide.
Summary of the invention
The technical problem to be solved is: provide the synthetic method of the new connection pyrazolecarboxamide analog derivative of the pyrimidine containing furan, this kind of compound modulates agricultural, gardening and forestry weeds and the biological activity of the phytopathy original and assay method thereof are provided, the application in agriculture field, horticultural field, field of forestry of these compounds is provided simultaneously.
The present invention solves this technical problem and be the technical scheme is that the chemical structure of general formula of the connection pyrazolecarboxamide analog derivative of the pyrimidine containing furan with agriculture field, horticultural field, field of forestry weeding and bactericidal activity is shown in Formula V:
Wherein, R is selected fromX is selected from S and O；R2Selected from H, CF3、F、Cl；R3Selected from H, CF3、F、Cl；R4Selected from H, CF3、F、Cl、NO2、OCH3；R5Selected from H and F；R6Selected from H and Cl；R7Selected from H and Cl；R8Selected from H and CF3；The synthetic method of the connection pyrazolecarboxamide analog derivative V of the pyrimidine containing furan of the present invention is as follows:
Wherein, R is selected fromX is selected from S and O；R2Selected from H, CF3、F、Cl；R3Selected from H, CF3、F、Cl；R4Selected from H, CF3、F、Cl、NO2、OCH3；R5Selected from H and F； R6Selected from H and Cl；R7Selected from H and Cl；R8Selected from H and CF3；
The synthetic method of compound V is specifically divided into following steps:
The preparation of A intermediate III:
2.00 grams are added in two mouthfuls of round-bottomed flasks of 100 milliliters, the furoyl acetonitrile of i.e. 14.8 mMs, with 20 milliliters of anhydrous alcohol solutions, the intermediate compound I of rear addition 14.8 mMs, heating reflux reaction, TLC monitors reaction process, react rear removal of solvent under reduced pressure dehydrated alcohol, residue obtains intermediate III through 200～300 mesh silica gel column chromatography purification, eluant volume ratio is methylene chloride/methanol=60/1, yield is 87%, and amount and the volume of reaction vessel prepared by intermediate III are expanded or shunk by corresponding proportion；
The preparation of B intermediate compound IV:
In 100 milliliters of two mouthfuls of round-bottomed flasks, add the intermediate II of 5.00 mMs, in reaction, then add 10 milliliters of steamed thionyl chlorides of weight and 2 DMF, back flow reaction 5h, after having reacted into, reflux is changed distilling apparatus, steam the thionyl chloride of excess；Obtaining intermediate compound IV, intermediate compound IV is not required to purification, directly carries out the next step, yield 90-100%；Amount and the volume of reaction vessel prepared by intermediate compound IV are expanded or shunk by corresponding proportion；
The preparation of the C pyrimidine connection pyrazolecarboxamide analog derivative V containing furan:
nullThe intermediate III of 1.78 mMs is added in two mouthfuls of round-bottomed flasks of 100 milliliters，With the steamed dichloromethane dissolving of 20 milliliters of weights，It is subsequently adding 0.22 gram，The triethylamine of i.e. 2.13 mMs，The lower stirring of cryosel bath，When temperature is down to below 0 degree Celsius，Drip the intermediate compound IV of 2.13 mMs and the mixed solution of the steamed dichloromethane of 10 milliliters of weights，Drip and finish，Recover to normal-temperature reaction，TLC monitors reaction process，First three times are washed with the aqueous hydrochloric acid solution of 30 milliliter 3.6% after having reacted，To remove unreacted intermediate III completely，Then organic layer is successively with 30 milliliters of saturated sodium bicarbonate solutions、30 milliliters of saturated nacl aqueous solutions are respectively washed once，To remove the moisture in reactant liquor，Last organic layer anhydrous sodium sulfate is dried overnight，After removal of solvent under reduced pressure dichloromethane，Residue obtains compound V through 200～300 mesh silica gel column chromatography purification，By gained sterling calculated yield，Yield 42.81-90.35%；Amount and the volume of reaction vessel prepared by compound V are expanded or shunk by corresponding proportion, and chemical constitution and the physical and chemical parameter of compound V are shown in Table 1；
The Herbicidal of the connection pyrazolecarboxamide analog derivative V of the pyrimidine containing furan of the D present invention:
The activity of weeding of the connection pyrazolecarboxamide analog derivative V of the pyrimidine containing furan of the present invention uses stem and leaf facture, concretely comprise the following steps: take 50 milligrams of samples and be dissolved in appropriate dimethylformamide, then with the medicament being diluted to 1000 mcg/ml containing a certain amount of polysorbas20 emulsifier aqueous solution；nullTreat that broadleaf weed grew to for two leaf phases，When monocotyledon weed grew to for 3～5 leaf phase，Reagent agent use metered dose device be uniformly sprayed on grass cutting blade，Blank is done with the solution without sample，Often process and be repeated 3 times，Weeds after processing are cultivated in being placed on artificial climate incubator，The sample suppression degree to weed growth is investigated by ocular estimate after 24h，Test plant is kind and the model plant arabidopsis of the major part typical case weeds that in China's agricultural production, field actually occurs，Its title is as follows: Herba Digitariae，Its Latin is entitled: Digitaria sanguinalis L.、Herba Setariae Viridis，Its Latin is entitled: Setaria viridis L.、Amaranthus retroflexus，Its Latin is entitled: Amaranthus retroflexus L.、Herba Portulacae，Its Latin is entitled: Portulaca oleracea L.、Arabidopsis，Its Latin is entitled: Arabidopsis thaliana、Barnyard grass，Its Latin is entitled: Echinochloa crus-galli L.
The bactericidal activity of the connection pyrazolecarboxamide analog derivative V of the pyrimidine containing furan of the E present invention measures:
nullSterilization or the bacteriostatic activity of the connection pyrazolecarboxamide analog derivative V of the pyrimidine containing furan of the present invention use thalli growth rate algoscopy，Concretely comprise the following steps: take 2.0 milligrams of samples and be dissolved in appropriate dimethylformamide，Then the medicament of 500 mcg/ml it is diluted to sterilized water，Reagent agent is respectively drawn 1 milliliter inject in culture dish，It is separately added into 9 milliliters of PDA culture medium again，50 mcg/ml pastille flat boards are made after shaking up，Blank is done with the flat board of 1 milliliter of aquesterilisa of interpolation，Bacterium dish is cut along mycelia outer rim with the card punch of diameter 4 millimeters，Move on pastille flat board，Put in equilateral triangle，Often process and be repeated 3 times，Cultivate in culture dish is placed on 24 ± 1 degrees Celsius of constant incubators，Colony diameter to be compareed expands to 2-3 centimetre of " Invest, Then Investigate " and respectively processes bacterium dish extension diameter，Average，The relative bacteriostasis rate of calculating is compared with blank，It is the kind of most of typical plant pathogen that field actually occurs in China's agricultural production for examination strain，Its code name and title are as follows: AS: tomato early blight bacterium，Its Latin is entitled: Alternaria solani、BC: botrytis cinerea pers，Its Latin is entitled: Botrytis cinerea、CA: peanut Cercospora bacteria，Its Latin is entitled: Cercospora arachidicola、GZ: fusarium graminearum，Its Latin is entitled: Gibberella zeae、PI: phytophthora infestans，Its Latin is entitled: Phytophthorainfestans (Mont.) de Bary、PP: Botryosphaeria berengeriana f. sp，Its Latin is entitled: Physalospora piricola、PS: Rhizoctonia solani Kuhn，Its Latin is entitled: Pellicularia sasakii、RC: Rhizoctonia cerealis，Its Latin is entitled: Rhizoctoniacerealis、SS: Sclerotinia sclerotiorum，Its Latin is entitled: Sclerotinia sclerotiorum；
The invention has the beneficial effects as follows: the pyrimidine containing furan is joined pyrazolecarboxamide analog derivative V and has carried out derivative synthesis, and the noval chemical compound synthesized has been carried out the screening of weeding and bactericidal activity.
The synthesis of present invention pyrimidine connection pyrazolecarboxamide analog derivative V containing furan by specific preparation and the more specific explanation of biological activity determination embodiment and biological activity and application, described embodiment is only used for illustrating the present invention and the unrestricted present invention, especially biological activity is merely illustrative of, and unrestricted this patent, detailed description of the invention is as follows:
Embodiment 1
The preparation of intermediate III:
2.00 grams are added in two mouthfuls of round-bottomed flasks of 100 milliliters, the furoyl acetonitrile of i.e. 14.8 mMs, with 20 milliliters of anhydrous alcohol solutions, rear addition 1.63 grams, the 2-hydrazinopyrimidine of i.e. 14.8 mMs, heating reflux reaction, TLC monitors reaction process, having reacted rear removal of solvent under reduced pressure dehydrated alcohol, residue obtains intermediate III through 200～300 mesh silica gel column chromatography purification, and eluant volume ratio is methylene chloride/methanol=60/1；With gained sterling calculated yield yield 87%.1H NMR (400MHz, CDCl3) δ 8.78 (d, J=4.8Hz, 2H), 7.49 (d, J=1.0Hz, 1H), 7.16 (t, J=4.8Hz, 1H), 6.93 (d, J=3.4Hz, 1H), 6.49 (dd, J=3.3,1.8Hz, 1H), 5.98 (s, 2H), 5.86 (s, 1H).
Embodiment 2
The preparation of intermediate compound IV:
In 100 milliliters of two mouthfuls of round-bottomed flasks, add the intermediate II of 5.00 mMs, in reaction, then add 10 milliliters of steamed thionyl chlorides of weight and 2 DMF, back flow reaction 5h, after having reacted into, reflux is changed distilling apparatus, steam the thionyl chloride of excess.Obtaining intermediate compound IV, intermediate compound IV is not required to purification, directly carries out the next step.Yield 90-100%.
Embodiment 3
The preparation of the pyrimidine connection pyrazolecarboxamide analog derivative V containing furan:
The intermediate III of 1.78 mMs is added in two mouthfuls of round-bottomed flasks of 100 milliliters, with the steamed dichloromethane dissolving of 20 milliliters of weights, it is subsequently adding 0.22 gram, the triethylamine of i.e. 2.13 mMs, the lower stirring of cryosel bath, when temperature is down to below 0 degree Celsius, drips the intermediate compound IV of 2.13 mMs and the mixed solution of the steamed dichloromethane of 10 milliliters of weights, drip and finish, recover to normal-temperature reaction.TLC monitors reaction process, first three times are washed with the aqueous hydrochloric acid solution of 30 milliliter 3.6% after having reacted, to remove unreacted intermediate III completely, then organic layer is respectively washed once with 30 milliliters of saturated sodium bicarbonate solutions, 30 milliliters of saturated nacl aqueous solutions successively, to remove the moisture in reactant liquor, last organic layer anhydrous sodium sulfate is dried overnight.After removal of solvent under reduced pressure dichloromethane, residue obtains compound V through 200～300 mesh silica gel column chromatography purification, with gained sterling calculated yield, yield 42.81-90.35%.
Embodiment 4
Pyrimidine containing the furan connection pyrazolecarboxamide analog derivative V Herbicidal result of the present invention:
Common weed and the model plant title of present invention test are as follows: Herba Digitariae, its Latin is entitled: Digitaria sanguinalisL., Herba Setariae Viridis, its Latin is entitled: Setaria viridis L., Amaranthus retroflexus, and its Latin is entitled: Amaranthus retroflexus L., Herba Portulacae, its Latin is entitled: Portulaca oleracea L., barnyard grass, and its Latin is entitled: Echinochloa crusgalliL. model plant arabidopsis, its Latin is entitled: Arabidopsis thaliana.These weeds kinds have good representativeness, it is possible to represent most of weeds that in agricultural production, field occurs.Weeding biological activity determination the results are shown in Table 2, and table 2 shows, when 1000 mcg/ml, all compounds of present invention synthesis all have activity of weeding in various degree.For Herba Digitariae, the suppression grade of compound HUO-XA-a, HUO-XA-9, HUO-XA-17, HUO-XA-19, HUO-XA-21, HUO-XA-55 reaches more than 3 grades.Wherein, the suppression grade of compound HUO-XA-17, HUO-XA-19, HUO-XA-21, HUO-XA-55 exceeds 1 grade of intermediate HUO-XA-a.For Herba Setariae Viridis, the suppression grade of compound HUO-XA-9, HUO-XA-14, HUO-XA-17, HUO-XA-19, HUO-XA-21, HUO-XA-55 reaches 3 grades, exceeding 2 grades of intermediate HUO-XA-a, remaining derivant suppression grade is identical with intermediate HUO-XA-a or exceeds 1 grade.For barnyard grass, the suppression grade of compound HUO-XA-14, HUO-XA-17, HUO-XA-19, HUO-XA-21, HUO-XA-55 reaches 3 grades, exceeds 2 grades of intermediate HUO-XA-a.For Amaranthus retroflexus, the suppression grade of compound HUO-XA-5, HUO-XA-19, HUO-XA-25, HUO-XA-40, HUO-XA-43, HUO-XA-52, HUO-XA-55, HUO-XA-58, HUO-XA-66 reaches more than 3 grades.Wherein, the suppression grade of compound HUO-XA-19 reaches 5 grades, exceeds 3 grades of intermediate HUO-XA-a.For Herba Portulacae, the suppression grade of compound HUO-XA-5, HUO-XA-19, HUO-XA-55, HUO-XA-56, HUO-XA-58, HUO-XA-66 reaches more than 3 grades, and the suppression grade of these compounds exceeds 2 or 3 grades of intermediate HUO-XA-a.For arabidopsis, the suppression grade of compound HUO-XA-5, HUO-XA-19, HUO-XA-25, HUO-XA-40, HUO-XA-48, HUO-XA-55, HUO-XA-63, HUO-XA-69 reaches more than 3 grades, wherein, the suppression grade of compound HUO-XA-5, HUO-XA-19 reaches 5 grades, exceeds 4 grades of intermediate HUO-XA-a.Therefore, the connection pyrazolecarboxamide analog derivative of the pyrimidine containing furan of the present invention makes it have activity of weeding in various degree due to the introducing of different activity of weeding groups.
Embodiment 5
Pyrimidine containing the furan connection pyrazolecarboxamide analog derivative V Antibacterial Activity result of the present invention:
nullCode name and the title of the frequently seen plants pathogenic fungi of present invention test are as follows: AS: tomato early blight bacterium，Its Latin is entitled: Alternaria solani、BC: botrytis cinerea pers，Its Latin is entitled: Botrytis cinerea、CA: peanut Cercospora bacteria，Its Latin is entitled: Cercospora arachidicola、GZ: fusarium graminearum，Its Latin is entitled: Gibberellazeae、PI: phytophthora infestans，Its Latin is entitled: Phytophthora infestans (Mont.) de Bary、PP: Botryosphaeria berengeriana f. sp，Its Latin is entitled: Physalospora piricola、PS: Rhizoctonia solani Kuhn，Its Latin is entitled: Pellicularia sasakii、RC: Rhizoctonia cerealis，Its Latin is entitled: Rhizoctonia cerealis、SS: Sclerotinia sclerotiorum，Its Latin is entitled: Sclerotinia sclerotiorum，These strains have good representativeness，The kind of most of pathogen that field occurs in agricultural production can be represented.Thalli growth rate method measurement result is shown in Table 3, and table 3 shows, when 50 mcg/ml, all compounds of present invention synthesis all have bactericidal activity in various degree.For Phytophthora infestans, the suppression ratio of compound HUO-XA-7 more than 55%, bactericidal activity exceed comparison medicament Fluoxastrobin more than 10%, exceed intermediate HUO-XA-a more than 40%.For peanut Cercospora bacteria, the suppression ratio of compound HUO-XA-43, HUO-XA-54 is more than 40%, and bactericidal activity exceeds intermediate HUO-XA-a about 10%.For Alternaria solani, the suppression ratio of compound HUO-XA-7, HUO-XA-9, HUO-XA-48, HUO-XA-54, HUO-XA-55, HUO-XA-58, HUO-XA-63, HUO-XA-66, HUO-XA-69 is more than 40%.Wherein the suppression ratio of compound HUO-XA-66 is more than 60%, and bactericidal activity exceeds intermediate HUO-XA-a about 30%.For botrytis cinerea pers, the suppression ratio of compound HUO-XA-a, HUO-XA-7, HUO-XA-9, HUO-XA-11, HUO-XA-17, HUO-XA-43, HUO-XA-48, HUO-XA-52, HUO-XA-66 is more than 40%.Wherein the suppression ratio of intermediate HUO-XA-a reaches 75%, and the activity of all derivants is below this intermediate.For fusarium graminearum, the suppression ratio of compound HUO-XA-9, HUO-XA-29, HUO-XA-43, HUO-XA-52, HUO-XA-56, HUO-XA-58, HUO-XA-66 is more than 40%.Wherein, the suppression ratio of compound HUO-XA-66 reaches 68%, and bactericidal activity exceeds intermediate HUO-XA-a more than 30%.For Botryosphaeria berengeriana f. sp, the suppression ratio of compound HUO-XA-a, HUO-XA-7, HUO-XA-29 is more than 50%.Wherein, the suppression ratio of compound HUO-XA-a reaches 63.04%, and the activity of all derivants is below this intermediate.For Sclerotinia sclerotiorum, the suppression ratio of all compounds is more than 40%, and wherein the suppression ratio of compound HUO-XA-9, HUO-XA-11, HUO-XA-19, HUO-XA-21 is higher than 85%, and bactericidal activity exceeds intermediate HUO-XA-a more than 30%.For Rhizoctonia cerealis, the suppression ratio of compound HUO-XA-7, HUO-XA-43, HUO-XA-52 is more than 30%, and bactericidal activity exceeds intermediate HUO-XA-a more than 20%.For Rhizoctonia solani Kuhn, compound HUO-XA-5, the suppression ratio of HUO-XA-7, HUO-XA-9, HUO-XA-21, HUO-XA-29 more than 40%, bactericidal activity exceeds intermediate HUO-XA-a about 20%.Therefore, the present invention designs the noval chemical compound of synthesis owing to introducing the difference of substituent group, and target compound all has different bactericidal activities.
Embodiment 6
Pyrimidine containing the furan connection pyrazolecarboxamide analog derivative V of the present invention and any one or more combination in the most acceptable auxiliary agent and the following Commercial herbicides purposes in preparing complex weedicide:
nullDescribed Commercial herbicides is selected from nicosulfuron、Tribenuron-methyl、Single cinosulfuron、Sulfometuronmethyl、Penoxsuam、Alachlor、Acetochlor、Butachlor、Isopropyl methoxalamine、2 first 4 chlorine、Trefanocide、Mesotrione、Mesotrione、Topramezone、Pendimethalin、Atrazine、Prometryn、Cyanazine、Ametryn、Metribuzin、Nitrofen、Oxyfluorfen、Acifluorfen、Lactofen、Fluoroglycofen-ethyl、Pyraflufen-ethyl、Fluazolate、Imazapyr、Imazethapyr、Miaow oxalic acid、Imazaquin、Imazamox、Imazapic、Pyrithiobacsodium、KIH 6127、Bispyribac-sodium、Pyribenzoxim、Pyriftalid、Phenmedipham、Desmedipham、Herba ainsliaeae yunnanensis、Imugan、Pyributicarb、Esprocarb、Prosulfocarb、Fluazifop、Haloxyfop、Fenoxaprop-P、Quizalofop-ethyl、Diclofop-methyl thiazole、Fluroxypyr、Dithiopyr、Fluorine pyridine ketone、Thiazopyr、Diflufenzopyr、N,N'-dimethyl-.gamma..gamma.'-dipyridylium、Glyphosate、Dried tuber barnyard grass、Flumiclorac pentyl、Flumioxazin、Fluthiacet-methyl、Fluthiacet、Pyrazolate、Benzofenap、Pyrazoxyfen、Isoxaflutole、Isoxachlorotole、Brominal etc.；Pyrimidine containing the furan connection pyrazolecarboxamide analog derivative V total weight/mass percentage composition in gained complex weedicide of the present invention is 1%-90%, and the connection pyrazolecarboxamide analog derivative V of the pyrimidine containing furan of the present invention is mass percent 1%: 99% to 99%: 1% with the ratio of described Commercial herbicides；nullAny one in the following dosage forms of the dosage form that described complex weedicide is suitable for: wettable powder、Micro-capsule suspension、Dispersible body preparation、Dispersible solid preparation、Seed treatment Emulsion、Aqueous emulsion、Big granule、Microemulsion、Oil-suspending agent、Water-soluble granule、Soluble thick agent、Water-dispersible granules、Poison grain、Aerosol、Sustained-release block、CG/Encapsulated granule、Waterless Seed Dressing powder、Cream、Electrostatic spray agent、Water in oil emulsion、Oil in water emulsion、Smoke candle、Granula subtilis、Smoke candle、Smoke cartridge、Smog rod、Seed treatment suspending agent、Smog sheet、Smog ball、Foaming agent、Drift powder、Ointment、Thermal fog、Solid-liquid mixing dress agent、Liquid liquid mixing dress agent、Cold mist agent、Gu Gu/mixing dress agent、Medicine paint、Seed treatment liquor、Microgranule、Oil-dispersing property powder、Dense colloid、Sprinkle and water agent、Liniment、Suspended emulsion、Film forming oil preparation、Soluble powder、Seed treatment water solube powder、Ultra-low volume suspending agent、Follow the trail of powder、Ultra low volume liquids、Steam releasing agent、Wet-mixing kind water-dispersible powder；The plant that described complex weedicide is suitable for is selected from Oryza glutinosa, Semen Tritici aestivi, Fructus Hordei Vulgaris, Herba bromi japonici, Semen Maydis, Sorghum vulgare Pers., Rhizoma Dioscoreae esculentae, Rhizoma Solani tuber osi, Maninot esculenta crantz., Semen sojae atricolor, garden pea, Semen Viciae fabae, Semen Pisi sativi, Semen phaseoli radiati, Semen Phaseoli, Cotton Gossypii, silkworm and mulberry, Semen arachidis hypogaeae, Brassica campestris L, Semen Sesami, Helianthi, Radix Betae, Caulis Sacchari sinensis, coffee, cocoa, Radix Ginseng, Bulbus Fritillariae Uninbracteatae, rubber, Cortex cocois radicis, Elaeis guineensis Jacq., Folium Agaves Sisalanae, Nicotiana tabacum L., Fructus Lycopersici esculenti, Fructus Capsici, Radix Raphani, Fructus Cucumidis sativi, Chinese cabbage, Herba Apii graveolentis, hot pickled mustard tube, Radix Betae, Brassica campestris L, Herba Alii fistulosi, Bulbus Allii, Citrullus vulgaris, Fructus Melo, hami melon, Fructus Chaenomelis, Fructus Mali pumilae, mandarin orange, peach tree, tea, wild vegetable, bamboo sprout, Flos lupuli (Flos Humuli Lupuli), Fructus Piperis, Fructus Musae, Fructus Caricae, Cymbidium ensifolium (L.) Sw., potted landscape；The controlling weeds that described complex weedicide is suitable for is selected from: grassy weed: Herba Digitariae, Herba Setariae Viridis, Herba Eleusines Indicae, barnyard grass, Semen Euphorbiae, Radix seu Caulis Embeliae Parviflorae, wild oat, Herba Eragrostidis pilosae, Setaria glauca, long awns caput grass, amur foxtail etc.；Broad leaved weed: Amaranthus retroflexus, Herba Portulacae, Herba chenopodii, descurainia sophia (l.) webb ex prantl, Herba Acalyphae, Herba Xanthii, artemisiifolia, Amaranthus, Herba Abutili, Fructus Kochiae, Herba Solani Nigri, Folium Salicis Babylonicae thorn knotweed, Herba stellariae mediae, Herba Moslae, water Spina jujubae, pale persicaria, DAWANHUA, Herba seu Flos Convolvuli arvensis, Semen Cuscutae etc.；Sedge weed: Herba Eleocharitis acicularis, the opposite sex dried tuber, Herba Cyperi Glomerati, Herba Salsolae Collinae, Herba Scirpi Tabernaemontani etc..
Embodiment 7
Pyrimidine containing the furan connection pyrazolecarboxamide analog derivative V of the present invention and any one or more combination in the most acceptable auxiliary agent and the following commodity antibacterial purposes in preparing composite bactericide:
nullDescribed commodity antibacterial is selected from: diazosulfide、Tiadinil，It is abbreviated as TDL、Tisocromide、First thiophene lures amine、4-methyl isophthalic acid，2，3-thiadiazoles-5-formic acid、4-methyl isophthalic acid，2，3-thiadiazoles-5-sodium formate、4-methyl isophthalic acid，2，3-thiadiazoles-5-Ethyl formate、DL-beta-aminobutyric acid、Isotianil，It is English general entitled: isotianil、3，4-bis-chloroisothiazole-5-formic acid、3，4-bis-chloroisothiazole-5-sodium formate、3，4-bis-chloroisothiazole-5-Ethyl formate、Virazole、Antofine、Ningnanmycin or salicylic acid、Cymoxanil、Thiram、Ziram、Mancozeb、AL-PHOSETHYL aluminum tris(ethyl phosphite)、Thiophanate-methyl、Bravo、Enemy can pine、Procymidone、Fenpropidin、Thiophanate methyl、Thiophanate、Metalaxyl-M、Flumorph、Dimethomorph、Mefenoxam、Benalaxyl-M、Double chlorine zarilamids、Flusulfamide、First flusulfamide、Thiophene fluorine bacterium amine、Flutolanil、Tecloftalam、Ring propionyl bacterium amine、Cyflufenamid、Fenhexamid、Zarilamid、Silthiopham、Furametpyr、Pyrrole metsulfovax、Mandipropamid、Zoxamide、Fenfuram、Carboxin、Chlozolinate、RP-26019、Fluoxastrobin、Dimoxystrobin、Fluoxastrobin、Kresoxim-methyl、SSF 126、Orysastrobin、ZEN 90160、Pyraclostrobin、Trifloxystrobin、Enestroburin、Alkene oxime amine、Oxygen ring azoles、Bromuconazole、SAN-619F、Difenoconazole、Olefin conversion、Efficiently olefin conversion、Epoxiconazole、RH-7592、Fluquinconazole、Bis(4-fluorophenyl)methyl(1H-1,2,4-triazol-1-ylmethyl)silane、Flutriafol、Hexaconazole、Glyoxalin、Plant bacterium azoles、Metconazole、Nitrile bacterium azoles、Wu Junzuo、Propiconazole、Prothioconazoles、Simeconazoles、Tebuconazole、Tetraconazole、Triadimenol、Triticonazole、Bitertanol、Probenazole、Furidazol、Imazalil、Efficiently imazalil、Prochloraz、Fluorine bacterium azoles、Cyazofamid、Fenamidone、Imidazoles、Pefurazoate、Cycloheximide triazole、Pyridine bacterium azoles、Mould spirit、Frost spirit、Guardian、Grandox fumigant、Octhilinone、Benthiozole、Dodemorph、Butadiene morpholine、Tridemorph、Fenpiclonil、CGA-173506、Fluazinam、Pyrifenox、Ring pyridine bacterium amine、Boscalid、Fluopicolide、Pyridine bacterium amine、Cyprodinil、Fluorine mepanipyrim、Ferimzone、Mepanipyrim、Pyrimethanil、Fenarimol、Nuarimol、Chinomethionat、Dithianon、Ethoxyquin、Hydroxyquinoline、Third oxygen quinoline、Quinoxyfen、Diethofencarb、Iprovalicarb、Benzene metsulfovax、Propamocarb、Methasulfocarb、Edifenphos、Iprobenfos、Pyrazophos、Tolelofos-methyl、Blasticidin-S、Kasugarnycin、Polyoxin、Polyoxin、Valida、Jingganmycin、Streptomycin、Metalaxyl、Furalaxyl、M 9834、Ofurace、Mebenil、Carbendazim、Benomyl、Thiophanate-methyl、Triazolone、Bupirimate、Dimethirimol、Ethirimol、Difoltan、Captan、Folpet、Vinclozolin、Fluoromide、Dimethachlon、Bravo、Isoprothiolane、Kitazine、Yekuzuo、Pentachloronitrobenzene、Propineb、Phosethyl-Al、Sulfur、Bordeaux mixture、Copper sulfate、Copper oxychloride、Red copper oxide、Copper hydrate、Metrafenone、Pencycuron、Diclomezin、Rabcide、Pyroquilon、Volution bacterium amine、Tricyclazole、Triforine、The pyridine of many fruits、The pungent salt of biguanide、Iminoctadine、Botran、Benzene flusulfamide、Toluene flusulfamide、Indocate、Fenaminosulf、Oxolinic acide、Probenazole、Bronopol、Iodomethane、Metham-sodium、Enemy's line ester、Dazomet、Nemamort、Lythidathion、Cadusafos、O,O-diethyl O-[p-(methylsulfinyl)phenyl、Thionazin、Fenamiphos、Phonamiphos、O-2,4-dichlorophenyl O,O-diethyl phosphorothioate、Isazofos、Fosthietan、Oxamyl、Aldicarb、Carbofuran、Vikane、Dichloropropylene、Dichloro-isonicotinic acid、Allyl isothiazole；Pyrimidine containing the furan connection pyrazolecarboxamide analog derivative V total weight/mass percentage composition in described bactericidal composition of the present invention is 1%-90%, and the connection pyrazolecarboxamide analog derivative V of the pyrimidine containing furan of the present invention is mass percent 1%: 99% to 99%: 1% with the ratio of aforementioned commodity antibacterial；The dosage form of described bactericidal composition processing is selected from: seed treatment Emulsion, aqueous emulsion, microemulsion, suspension emulsion, capsule suspension, water-soluble granule, granula subtilis, soluble thick agent, poison grain, block poison bait, granular poison bait, lamellar poison bait, dense poison bait, sustained-release block, electrostatic spray agent, oil in water emulsion, smoke candle, smoke candle, smoke cartridge, smog rod, smog sheet, smog ball, foaming agent, ointment, thermal fog, cold mist agent, aerosol, solid-liquid mixing dress agent, liquid liquid mixing dress agent, Gu Gu/mixing dress agent, medicine paint, microgranule, follow the trail of powder, oil suspending agent, oil-dispersing property powder, dense colloid, sprinkle and water agent, seed coat agent, liniment, film forming oil preparation, ultra low volume liquids, steam releasing agent；The plant disease of described bactericidal composition preventing and treating is selected from: seedling blight of rice, tomato root maize ear rot, the late blight of potato, black shank, millet powdery mildew, downy mildew of garpe, downy mildew of lettuce, cucumber downy mildew, cucumber anthracnose；The plant that described bactericidal composition is suitable for is selected from: Oryza glutinosa, Semen Tritici aestivi, Fructus Hordei Vulgaris, Herba bromi japonici, Semen Maydis, Sorghum vulgare Pers., Rhizoma Dioscoreae esculentae, Rhizoma Solani tuber osi, Maninot esculenta crantz., Semen sojae atricolor, garden pea, Semen Viciae fabae, Semen Pisi sativi, Semen phaseoli radiati, Semen Phaseoli, Cotton Gossypii, silkworm and mulberry, Semen arachidis hypogaeae, Brassica campestris L, Semen Sesami, Helianthi, Radix Betae, Caulis Sacchari sinensis, coffee, cocoa, Radix Ginseng, Bulbus Fritillariae Uninbracteatae, rubber, Cortex cocois radicis, Elaeis guineensis Jacq., Folium Agaves Sisalanae, Nicotiana tabacum L., Fructus Lycopersici esculenti, Fructus Capsici, Radix Raphani, Fructus Cucumidis sativi, Chinese cabbage, Herba Apii graveolentis, hot pickled mustard tube, Radix Betae, Brassica campestris L, Herba Alii fistulosi, Bulbus Allii, Citrullus vulgaris, Fructus Melo, hami melon, Fructus Chaenomelis, Fructus Mali pumilae, mandarin orange and peach tree, tea, wild vegetable, bamboo sprout, Flos lupuli (Flos Humuli Lupuli), Fructus Piperis, Fructus Musae, Fructus Caricae, Cymbidium ensifolium (L.) Sw., potted landscape.
The chemical constitution of the connection pyrazolecarboxamide analog derivative V of the pyrimidine containing furan of table 1 present invention and physical and chemical parameter
The activity of weeding (the suppression grades of 1000 mcg/ml) of the connection pyrazolecarboxamide analog derivative of the pyrimidine containing furan of table 2 present invention
Sequence number Compound Herba Digitariae Herba Setariae Viridis Barnyard grass Amaranthus retroflexus Herba Portulacae Arabidopsis
1 HUO-XA-a 3 1 1 2 1 1
2 HUO-XA-2 1 1 1 2 1 1
3 HUO-XA-5 2 2 1 4 3 5
4 HUO-XA-7 2 2 1 1 1 1
5 HUO-XA-9 3 3 2 1 1 1
6 HUO-XA-11 0 1 0 1 1 0
7 HUO-XA-14 4 3 3 1 1 0
8 HUO-XA-17 4 3 3 1 1 1
9 HUO-XA-19 4 3 3 5 4 5
10 HUO-XA-21 4 3 3 1 1 1
11 HUO-XA-23 1 1 1 1 1 1
12 HUO-XA-25 1 1 1 3 2 3
13 HUO-XA-27 1 1 2 1 2 2
14 HUO-XA-29 2 2 2 1 2 1
15 HUO-XA-40 1 1 1 3 2 3
16 HUO-XA-43 1 1 1 3 2 2
17 HUO-XA-48 2 1 1 2 2 3
18 HUO-XA-52 2 2 2 3 1 2
19 HUO-XA-54 1 1 1 2 2 2
20 HUO-XA-55 4 3 3 4 4 4
21 HUO-XA-56 2 1 1 2 3 2
22 HUO-XA-58 2 1 2 3 3 2
23 HUO-XA-63 2 2 1 2 2 3
24 HUO-XA-66 1 1 1 3 3 2
25 HUO-XA-69 2 1 2 2 2 3
Note: 0 grade, growth inhibition ratio is with comparison；1 grade, growth inhibition ratio ＜ 25%；2 grades, growth inhibition ratio is between 25%～50%；3 grades, growth inhibition ratio is between 50%～75%；4 grades, between growth inhibition ratio 75%～95%；5 grades, growth inhibition ratio ＞ 95%.
The bacteriostatic activity (suppression ratio/% of 50 mcg/ml) of the connection pyrazolecarboxamide analog derivative of the pyrimidine containing furan of table 3 present invention
Sequence number Compound PI CA AS BC GZ PP SS RC PS
1 HUO-XA-a 15.15 31.58 33.33 75.00 35.90 63.04 54.55 8.00 22.22
2 HUO-XA-2 7.69 35.29 28.57 21.43 16.13 16.67 85.00 0 36.00
3 HUO-XA-5 11.54 23.53 33.33 35.71 22.58 16.67 73.33 7.41 40.00
4 HUO-XA-7 57.69 35.29 42.86 64.29 32.26 58.33 63.33 33.33 58.00
5 HUO-XA-9 15.38 32.35 45.24 64.29 56.45 0 86.67 14.81 48.00
6 HUO-XA-11 19.23 23.53 23.81 50.00 25.81 0 86.67 7.41 0
7 HUO-XA-14 15.38 5.88 19.05 0 16.13 0 83.33 7.41 28.00
8 HUO-XA-17 11.54 23.53 19.05 57.14 22.58 0 85.00 7.41 0
9 HUO-XA-19 11.54 5.88 23.81 35.71 22.58 16.67 86.67 7.41 30.00
10 HUO-XA-21 0 17.65 19.05 21.43 12.90 4.17 86.67 3.70 40.00
11 HUO-XA-23 15.38 11.76 14.29 35.71 19.35 25.00 83.33 0 0
12 HUO-XA-25 23.08 35.29 38.10 39.29 35.48 0 83.33 0 30.00
13 HUO-XA-27 11.54 0 28.57 21.43 3.23 8.33 83.33 7.41 20.00
14 HUO-XA-29 19.23 23.53 33.33 35.71 51.61 50.00 81.67 7.41 48.00
15 HUO-XA-40 25.93 20.00 19.23 37.50 36.00 0 65.22 11.54 17.24
16 HUO-XA-43 22.22 40.00 38.46 41.67 40.00 12.00 56.52 30.77 27.59
17 HUO-XA-48 22.22 26.67 46.15 50.00 20.00 8.00 58.70 15.38 17.24
18 HUO-XA-52 18.52 20.00 23.08 54.17 52.00 0 45.65 30.77 10.34
19 HUO-XA-54 25.93 46.67 58.33 38.46 28.00 0 71.74 19.23 27.59
20 HUO-XA-55 18.52 13.33 54.17 19.23 24.00 0 71.74 11.54 20.69
21 HUO-XA-56 18.52 26.67 33.33 34.62 48.00 0 84.78 19.23 20.69
22 HUO-XA-58 11.11 20.00 41.67 30.77 40.00 24.00 63.04 15.38 6.90
23 HUO-XA-63 14.81 26.67 45.83 26.92 36.00 12.00 63.04 11.54 24.14
24 HUO-XA-66 33.33 33.33 62.50 42.31 68.00 0 71.74 19.23 10.34
25 HUO-XA-69 18.52 20.00 50.00 30.77 36.00 20.00 73.91 11.54 24.14
26 Fluoxastrobin 46.88 55.56 75.00 91.18 71.43 100 88.10 84.06 80.77

Claims (6)

1. the class pyrimidine connection pyrazolecarboxamide analog derivative containing furan, it is characterised in that there is chemical structure of general formula shown as a formula V:
Wherein, R is selected fromX selected from S and O,R2Selected from H, CF3、F、Cl；R3Selected from H, CF3、F、Cl；R4Selected from H, CF3、F、Cl、NO2、OCH3；R5Selected from H and F,R6Selected from H and Cl；R7Selected from H and Cl,R8Selected from H and CF3；
2. the synthetic method of the connection pyrazolecarboxamide analog derivative V of the pyrimidine containing furan described in claim 1, concrete synthetic route is as follows:
Wherein, R is selected fromX is selected from S and O；R2Selected from H, CF3、F、Cl；R3Selected from H, CF3、F、Cl；R4Selected from H, CF3、F、Cl、NO2、OCH3；R5Selected from H and F,R6Selected from H and Cl；R7Selected from H and Cl,R8Selected from H and CF3、
The synthetic method of the connection pyrazolecarboxamide analog derivative of the pyrimidine containing furan described in claim 1 is divided into following steps:
The preparation of A intermediate III:
2.00 grams are added in two mouthfuls of round-bottomed flasks of 100 milliliters, the furoyl acetonitrile of i.e. 14.8 mMs, with 20 milliliters of anhydrous alcohol solutions, the intermediate compound I of rear addition 14.8 mMs, heating reflux reaction, TLC monitors reaction process, react rear removal of solvent under reduced pressure dehydrated alcohol, residue obtains intermediate III through 200～300 mesh silica gel column chromatography purification, and eluant volume ratio is methylene chloride/methanol=60/1, and yield is 87%；Amount and the volume of reaction vessel prepared by intermediate III are expanded or shunk by corresponding proportion；
The preparation of B intermediate compound IV:
The intermediate II of 5.00 mMs is added in 100 milliliters of two mouthfuls of round-bottomed flasks, then in reaction, add 10 milliliters of steamed thionyl chlorides of weight and 2 DMF, back flow reaction 5h, after having reacted, changes by reflux as distilling apparatus into, steam the thionyl chloride of excess, obtaining intermediate compound IV, intermediate compound IV is not required to purification, directly carries out the next step, yield 90-100%, amount and the volume of reaction vessel prepared by intermediate compound IV are expanded or shunk by corresponding proportion；
The preparation of the C pyrimidine connection pyrazolecarboxamide analog derivative V containing furan:
The intermediate III of 1.78 mMs is added in two mouthfuls of round-bottomed flasks of 100 milliliters, with the steamed dichloromethane dissolving of 20 milliliters of weights, it is subsequently adding 0.22 gram, the triethylamine of i.e. 2.13 mMs, the lower stirring of cryosel bath, when temperature is down to below 0 degree Celsius, drip the intermediate compound IV of 2.13 mMs and the mixed solution of the steamed dichloromethane of 10 milliliters of weights, drip and finish, recover to normal-temperature reaction, TLC monitors reaction process, first three times are washed with the aqueous hydrochloric acid solution of 30 milliliter 3.6% after having reacted, to remove unreacted intermediate III completely, then organic layer is successively with 30 milliliters of saturated sodium bicarbonate solutions, 30 milliliters of saturated nacl aqueous solutions are respectively washed once, to remove the moisture in reactant liquor, last organic layer anhydrous sodium sulfate is dried overnight；After removal of solvent under reduced pressure dichloromethane, residue obtains compound V through 200～300 mesh silica gel column chromatography purification, and with gained sterling calculated yield, yield 42.81-90.35%, amount and the volume of reaction vessel prepared by compound V are expanded or shunk by corresponding proportion.
3. the connection pyrazolecarboxamide analog derivative V of the pyrimidine containing furan described in claim 1 and the most acceptable auxiliary agent purposes in preparing herbicide.
4. the connection pyrazolecarboxamide analog derivative V of the pyrimidine containing furan described in claim 1 and the most acceptable auxiliary agent purposes in preparing antibacterial.
5. the connection pyrazolecarboxamide analog derivative V of the pyrimidine containing furan described in claim 1 and the combinations of herbicides purposes in preventing and treating agricultural and forestry and gardening weeds:
nullAny one or two kinds of combinations in the pyrimidine containing furan connection pyrazolecarboxamide analog derivative V and Commercial herbicides described in claim 1 form Herbicidal combinations and are used for preventing and treating agricultural and forestry and gardening weeds，Described Commercial herbicides is selected from nicosulfuron、Tribenuron-methyl、Single cinosulfuron、Sulfometuronmethyl、Penoxsuam、Alachlor、Acetochlor、Butachlor、Isopropyl methoxalamine、2 first 4 chlorine、Trefanocide、Mesotrione、Mesotrione、Topramezone、Pendimethalin、Atrazine、Prometryn、Cyanazine、Ametryn、Metribuzin、Nitrofen、Oxyfluorfen、Acifluorfen、Lactofen、Fluoroglycofen-ethyl、Pyraflufen-ethyl、Fluazolate、Imazapyr、Imazethapyr、Miaow oxalic acid、Imazaquin、Imazamox、Imazapic、Pyrithiobacsodium、KIH 6127、Bispyribac-sodium、Pyribenzoxim、Pyriftalid、Phenmedipham、Desmedipham、Herba ainsliaeae yunnanensis、Imugan、Pyributicarb、Esprocarb、Prosulfocarb、Fluazifop、Haloxyfop、Fenoxaprop-P、Quizalofop-ethyl、Diclofop-methyl thiazole、Fluroxypyr、Dithiopyr、Fluorine pyridine ketone、Thiazopyr、Diflufenzopyr、N,N'-dimethyl-.gamma..gamma.'-dipyridylium、Glyphosate、Dried tuber barnyard grass、Flumiclorac pentyl、Flumioxazin、Fluthiacet-methyl、Fluthiacet、Pyrazolate、Benzofenap、Pyrazoxyfen、Isoxaflutole、Isoxachlorotole、Brominal etc.；Pyrimidine containing the furan connection pyrazolecarboxamide analog derivative V total weight/mass percentage composition in gained complex weedicide of the present invention is 1%-90%, and the connection pyrazolecarboxamide analog derivative V of the pyrimidine containing furan of the present invention is mass percent 1%: 99% to 99%: 1% with the ratio of described Commercial herbicides；nullAny one in the following dosage forms of the dosage form that described complex weedicide is suitable for: wettable powder、Micro-capsule suspension、Dispersible body preparation、Dispersible solid preparation、Seed treatment Emulsion、Aqueous emulsion、Big granule、Microemulsion、Oil-suspending agent、Water-soluble granule、Soluble thick agent、Water-dispersible granules、Poison grain、Aerosol、Sustained-release block、CG/Encapsulated granule、Waterless Seed Dressing powder、Cream、Electrostatic spray agent、Water in oil emulsion、Oil in water emulsion、Smoke candle、Granula subtilis、Smoke candle、Smoke cartridge、Smog rod、Seed treatment suspending agent、Smog sheet、Smog ball、Foaming agent、Drift powder、Ointment、Thermal fog、Solid-liquid mixing dress agent、Liquid liquid mixing dress agent、Cold mist agent、Gu Gu/mixing dress agent、Medicine paint、Seed treatment liquor、Microgranule、Oil-dispersing property powder、Dense colloid、Sprinkle and water agent、Liniment、Suspended emulsion、Film forming oil preparation、Soluble powder、Seed treatment water solube powder、Ultra-low volume suspending agent、Follow the trail of powder、Ultra low volume liquids、Steam releasing agent、Wet-mixing kind water-dispersible powder；The plant that described complex weedicide is suitable for is selected from Oryza glutinosa, Semen Tritici aestivi, Fructus Hordei Vulgaris, Herba bromi japonici, Semen Maydis, Sorghum vulgare Pers., Rhizoma Dioscoreae esculentae, Rhizoma Solani tuber osi, Maninot esculenta crantz., Semen sojae atricolor, garden pea, Semen Viciae fabae, Semen Pisi sativi, Semen phaseoli radiati, Semen Phaseoli, Cotton Gossypii, silkworm and mulberry, Semen arachidis hypogaeae, Brassica campestris L, Semen Sesami, Helianthi, Radix Betae, Caulis Sacchari sinensis, coffee, cocoa, Radix Ginseng, Bulbus Fritillariae Uninbracteatae, rubber, Cortex cocois radicis, Elaeis guineensis Jacq., Folium Agaves Sisalanae, Nicotiana tabacum L., Fructus Lycopersici esculenti, Fructus Capsici, Radix Raphani, Fructus Cucumidis sativi, Chinese cabbage, Herba Apii graveolentis, hot pickled mustard tube, Radix Betae, Brassica campestris L, Herba Alii fistulosi, Bulbus Allii, Citrullus vulgaris, Fructus Melo, hami melon, Fructus Chaenomelis, Fructus Mali pumilae, mandarin orange, peach tree, tea, wild vegetable, bamboo sprout, Flos lupuli (Flos Humuli Lupuli), Fructus Piperis, Fructus Musae, Fructus Caricae, Cymbidium ensifolium (L.) Sw., potted landscape；The controlling weeds that described complex weedicide is suitable for is selected from: grassy weed: Herba Digitariae, Herba Setariae Viridis, Herba Eleusines Indicae, barnyard grass, Semen Euphorbiae, Radix seu Caulis Embeliae Parviflorae, wild oat, Herba Eragrostidis pilosae, Setaria glauca, long awns caput grass, amur foxtail etc.；Broad leaved weed: Amaranthus retroflexus, Herba Portulacae, Herba chenopodii, descurainia sophia (l.) webb ex prantl, Herba Acalyphae, Herba Xanthii, artemisiifolia, Amaranthus, Herba Abutili, Fructus Kochiae, Herba Solani Nigri, Folium Salicis Babylonicae thorn knotweed, Herba stellariae mediae, Herba Moslae, water Spina jujubae, pale persicaria, DAWANHUA, Herba seu Flos Convolvuli arvensis, Semen Cuscutae etc.；Sedge weed: Herba Eleocharitis acicularis, the opposite sex dried tuber, Herba Cyperi Glomerati, Herba Salsolae Collinae, Herba Scirpi Tabernaemontani etc..
6. the connection pyrazolecarboxamide analog derivative V of the pyrimidine containing furan described in claim 1 and the antimicrobial combination purposes in preventing and treating agricultural and forestry and gardening plant disease:
nullAny one or two kinds of combinations in the pyrimidine containing furan connection pyrazolecarboxamide analog derivative V and commodity antibacterial described in claim 1 form bactericidal compositions and are used for preventing and treating agricultural and forestry and gardening plant disease，Described commodity antibacterial is selected from: diazosulfide、Tiadinil，It is abbreviated as TDL、Tisocromide、First thiophene lures amine、4-methyl isophthalic acid，2，3-thiadiazoles-5-formic acid、4-methyl isophthalic acid，2，3-thiadiazoles-5-sodium formate、4-methyl isophthalic acid，2，3-thiadiazoles-5-Ethyl formate、DL-beta-aminobutyric acid、Isotianil，It is English general entitled: isotianil、3，4-bis-chloroisothiazole-5-formic acid、3，4-bis-chloroisothiazole-5-sodium formate、3，4-bis-chloroisothiazole-5-Ethyl formate、Virazole、Antofine、Ningnanmycin or salicylic acid、Cymoxanil、Thiram、Ziram、Mancozeb、AL-PHOSETHYL aluminum tris(ethyl phosphite)、Thiophanate-methyl、Bravo、Enemy can pine、Procymidone、Fenpropidin、Thiophanate methyl、Thiophanate、Metalaxyl-M、Flumorph、Dimethomorph、Mefenoxam、Benalaxyl-M、Double chlorine zarilamids、Flusulfamide、First flusulfamide、Thiophene fluorine bacterium amine、Flutolanil、Tecloftalam、Ring propionyl bacterium amine、Cyflufenamid、Fenhexamid、Zarilamid、Silthiopham、Furametpyr、Pyrrole metsulfovax、Mandipropamid、Zoxamide、Fenfuram、Carboxin、Chlozolinate、RP-26019、Fluoxastrobin、Dimoxystrobin、Fluoxastrobin、Kresoxim-methyl、SSF 126、Orysastrobin、ZEN 90160、Pyraclostrobin、Trifloxystrobin、Enestroburin、Alkene oxime amine、Oxygen ring azoles、Bromuconazole、SAN-619F、Difenoconazole、Olefin conversion、Efficiently olefin conversion、Epoxiconazole、RH-7592、Fluquinconazole、Bis(4-fluorophenyl)methyl(1H-1,2,4-triazol-1-ylmethyl)silane、Flutriafol、Hexaconazole、Glyoxalin、Plant bacterium azoles、Metconazole、Nitrile bacterium azoles、Wu Junzuo、Propiconazole、Prothioconazoles、Simeconazoles、Tebuconazole、Tetraconazole、Triadimenol、Triticonazole、Bitertanol、Probenazole、Furidazol、Imazalil、Efficiently imazalil、Prochloraz、Fluorine bacterium azoles、Cyazofamid、Fenamidone、Imidazoles、Pefurazoate、Cycloheximide triazole、Pyridine bacterium azoles、Mould spirit、Frost spirit、Guardian、Grandox fumigant、Octhilinone、Benthiozole、Dodemorph、Butadiene morpholine、Tridemorph、Fenpiclonil、CGA-173506、Fluazinam、Pyrifenox、Ring pyridine bacterium amine、Boscalid、Fluopicolide、Pyridine bacterium amine、Cyprodinil、Fluorine mepanipyrim、Ferimzone、Mepanipyrim、Pyrimethanil、Fenarimol、Nuarimol、Chinomethionat、Dithianon、Ethoxyquin、Hydroxyquinoline、Third oxygen quinoline、Quinoxyfen、Diethofencarb、Iprovalicarb、Benzene metsulfovax、Propamocarb、Methasulfocarb、Edifenphos、Iprobenfos、Pyrazophos、Tolelofos-methyl、Blasticidin-S、Kasugarnycin、Polyoxin、Polyoxin、Valida、Jingganmycin、Streptomycin、Metalaxyl、Furalaxyl、M 9834、Ofurace、Mebenil、Carbendazim、Benomyl、Thiophanate-methyl、Triazolone、Bupirimate、Dimethirimol、Ethirimol、Difoltan、Captan、Folpet、Vinclozolin、Fluoromide、Dimethachlon、Bravo、Isoprothiolane、Kitazine、Yekuzuo、Pentachloronitrobenzene、Propineb、Phosethyl-Al、Sulfur、Bordeaux mixture、Copper sulfate、Copper oxychloride、Red copper oxide、Copper hydrate、Metrafenone、Pencycuron、Diclomezin、Rabcide、Pyroquilon、Volution bacterium amine、Tricyclazole、Triforine、The pyridine of many fruits、The pungent salt of biguanide、Iminoctadine、Botran、Benzene flusulfamide、Toluene flusulfamide、Indocate、Fenaminosulf、Oxolinic acide、Probenazole、Bronopol、Iodomethane、Metham-sodium、Enemy's line ester、Dazomet、Nemamort、Lythidathion、Cadusafos、O,O-diethyl O-[p-(methylsulfinyl)phenyl、Thionazin、Fenamiphos、Phonamiphos、O-2,4-dichlorophenyl O,O-diethyl phosphorothioate、Isazofos、Fosthietan、Oxamyl、Aldicarb、Carbofuran、Vikane、Dichloropropylene、Dichloro-isonicotinic acid、Allyl isothiazole；The connection pyrazolecarboxamide analog derivative V total weight/mass percentage composition in described bactericidal composition of the pyrimidine containing furan described in claim 1 is 1%-90%, and the connection pyrazolecarboxamide analog derivative V of the pyrimidine containing furan described in claim 1 is mass percent 1%: 99% to 99%: 1% with the ratio of aforementioned commodity antibacterial；The dosage form of described bactericidal composition processing is selected from: seed treatment Emulsion, aqueous emulsion, microemulsion, suspension emulsion, capsule suspension, water-soluble granule, granula subtilis, soluble thick agent, poison grain, block poison bait, granular poison bait, lamellar poison bait, dense poison bait, sustained-release block, electrostatic spray agent, oil in water emulsion, smoke candle, smoke candle, smoke cartridge, smog rod, smog sheet, smog ball, foaming agent, ointment, thermal fog, cold mist agent, aerosol, solid-liquid mixing dress agent, liquid liquid mixing dress agent, Gu Gu/mixing dress agent, medicine paint, microgranule, follow the trail of powder, oil suspending agent, oil-dispersing property powder, dense colloid, sprinkle and water agent, seed coat agent, liniment, film forming oil preparation, ultra low volume liquids, steam releasing agent；The plant disease of described bactericidal composition preventing and treating is selected from: seedling blight of rice, tomato root maize ear rot, the late blight of potato, black shank, millet powdery mildew, downy mildew of garpe, downy mildew of lettuce, cucumber downy mildew, cucumber anthracnose；The plant that described bactericidal composition is suitable for is selected from: Oryza glutinosa, Semen Tritici aestivi, Fructus Hordei Vulgaris, Herba bromi japonici, Semen Maydis, Sorghum vulgare Pers., Rhizoma Dioscoreae esculentae, Rhizoma Solani tuber osi, Maninot esculenta crantz., Semen sojae atricolor, garden pea, Semen Viciae fabae, Semen Pisi sativi, Semen phaseoli radiati, Semen Phaseoli, Cotton Gossypii, silkworm and mulberry, Semen arachidis hypogaeae, Brassica campestris L, Semen Sesami, Helianthi, Radix Betae, Caulis Sacchari sinensis, coffee, cocoa, Radix Ginseng, Bulbus Fritillariae Uninbracteatae, rubber, Cortex cocois radicis, Elaeis guineensis Jacq., Folium Agaves Sisalanae, Nicotiana tabacum L., Fructus Lycopersici esculenti, Fructus Capsici, Radix Raphani, Fructus Cucumidis sativi, Chinese cabbage, Herba Apii graveolentis, hot pickled mustard tube, Radix Betae, Brassica campestris L, Herba Alii fistulosi, Bulbus Allii, Citrullus vulgaris, Fructus Melo, hami melon, Fructus Chaenomelis, Fructus Mali pumilae, mandarin orange and peach tree, tea, wild vegetable, bamboo sprout, Flos lupuli (Flos Humuli Lupuli), Fructus Piperis, Fructus Musae, Fructus Caricae, Cymbidium ensifolium (L.) Sw., potted landscape.
CN201610522817.4A 2016-07-06 2016-07-06 Furan-containing pyrimidine dipyrazole formamide derivatives, and preparation method and application thereof Pending CN105949179A (en)

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