CN106879599B - Application of the triazole sulfonates compounds in preventing paddy bacterial disease - Google Patents
Application of the triazole sulfonates compounds in preventing paddy bacterial disease Download PDFInfo
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- CN106879599B CN106879599B CN201710184382.1A CN201710184382A CN106879599B CN 106879599 B CN106879599 B CN 106879599B CN 201710184382 A CN201710184382 A CN 201710184382A CN 106879599 B CN106879599 B CN 106879599B
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- -1 triazole sulfonates compounds Chemical class 0.000 title claims abstract description 57
- 208000035143 Bacterial infection Diseases 0.000 title claims abstract description 28
- 208000022362 bacterial infectious disease Diseases 0.000 title claims abstract description 26
- 150000001875 compounds Chemical class 0.000 claims abstract description 93
- 241000209094 Oryza Species 0.000 claims abstract description 39
- 241000894006 Bacteria Species 0.000 claims abstract description 32
- 235000007164 Oryza sativa Nutrition 0.000 claims abstract description 31
- 235000009566 rice Nutrition 0.000 claims abstract description 31
- 230000002265 prevention Effects 0.000 claims abstract description 19
- 201000010099 disease Diseases 0.000 claims abstract description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 15
- 230000000855 fungicidal effect Effects 0.000 claims abstract description 9
- 239000000417 fungicide Substances 0.000 claims abstract description 9
- 238000006467 substitution reaction Methods 0.000 claims description 79
- 125000000217 alkyl group Chemical group 0.000 claims description 72
- 125000001424 substituent group Chemical group 0.000 claims description 67
- 229910052736 halogen Inorganic materials 0.000 claims description 56
- 150000002367 halogens Chemical class 0.000 claims description 56
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 53
- 125000003545 alkoxy group Chemical group 0.000 claims description 48
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 31
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 19
- 241001272684 Xanthomonas campestris pv. oryzae Species 0.000 claims description 12
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 10
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
- 238000004659 sterilization and disinfection Methods 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 4
- BVLCUZLVOPMLGD-UHFFFAOYSA-N 2h-triazole-4-sulfonic acid Chemical class OS(=O)(=O)C1=CNN=N1 BVLCUZLVOPMLGD-UHFFFAOYSA-N 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 7
- 230000000694 effects Effects 0.000 abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 156
- 238000002360 preparation method Methods 0.000 description 60
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- CHZCERSEMVWNHL-UHFFFAOYSA-N 2-hydroxybenzonitrile Chemical class OC1=CC=CC=C1C#N CHZCERSEMVWNHL-UHFFFAOYSA-N 0.000 description 25
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- 238000012360 testing method Methods 0.000 description 21
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- 125000003118 aryl group Chemical group 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
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- 239000000460 chlorine Substances 0.000 description 15
- 239000003960 organic solvent Substances 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
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- 125000001072 heteroaryl group Chemical group 0.000 description 10
- 239000000047 product Substances 0.000 description 10
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- 238000012545 processing Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- 230000003449 preventive effect Effects 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- RUBQQRMAWLSCCJ-UHFFFAOYSA-N 1,2-difluoro-4-nitrobenzene Chemical class [O-][N+](=O)C1=CC=C(F)C(F)=C1 RUBQQRMAWLSCCJ-UHFFFAOYSA-N 0.000 description 5
- 238000006350 Schiemann fluorination reaction Methods 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 150000003851 azoles Chemical class 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000012954 diazonium Substances 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 4
- 230000032050 esterification Effects 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
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- PTTUMBGORBMNBN-UHFFFAOYSA-N 1,2,3-trifluoro-5-nitrobenzene Chemical class [O-][N+](=O)C1=CC(F)=C(F)C(F)=C1 PTTUMBGORBMNBN-UHFFFAOYSA-N 0.000 description 3
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
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- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical class O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
- AZFNGPAYDKGCRB-XCPIVNJJSA-M [(1s,2s)-2-amino-1,2-diphenylethyl]-(4-methylphenyl)sulfonylazanide;chlororuthenium(1+);1-methyl-4-propan-2-ylbenzene Chemical compound [Ru+]Cl.CC(C)C1=CC=C(C)C=C1.C1=CC(C)=CC=C1S(=O)(=O)[N-][C@@H](C=1C=CC=CC=1)[C@@H](N)C1=CC=CC=C1 AZFNGPAYDKGCRB-XCPIVNJJSA-M 0.000 description 1
- ZVZXQIUPJUHZRZ-UHFFFAOYSA-N [N+](=O)([O-])C1=CC=CC=C1.[O] Chemical compound [N+](=O)([O-])C1=CC=CC=C1.[O] ZVZXQIUPJUHZRZ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical class ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 229910001947 lithium oxide Inorganic materials 0.000 description 1
- 150000002672 m-cresols Chemical class 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical class C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000021332 multicellular organism growth Effects 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052754 neon Inorganic materials 0.000 description 1
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical class [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229940090668 parachlorophenol Drugs 0.000 description 1
- FTDXCHCAMNRNNY-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1.OC1=CC=CC=C1 FTDXCHCAMNRNNY-UHFFFAOYSA-N 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 239000004304 potassium nitrite Substances 0.000 description 1
- 235000010289 potassium nitrite Nutrition 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229940126586 small molecule drug Drugs 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 238000013517 stratification Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001018 virulence Effects 0.000 description 1
- 239000012138 yeast extract Substances 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Abstract
The present invention relates to rice plant disease control fields, and in particular to application of the triazole sulfonates compounds in preventing paddy bacterial disease.Wherein, the triazole sulfonates compounds are one or more in formula (1) compound represented.Triazole sulfonates compounds provided by the invention can obtain excellent effect as fungicide to causing the bacterium of rice disease to have effective bactericidal effect in prevention paddy bacterial disease.
Description
Technical field
The present invention relates to rice plant disease control fields, and in particular to triazole sulfonates compounds are in prevention rice
Application in bacterial disease.
Background technology
Paddy bacterial disease is main a kind of disease during paddy growth comprising bacterial blight of rice, rice
Slice disease etc..The prevention of paddy bacterial disease at present includes biological control and chemical prevention, and chemical prevention mainly passes through exploitation
Small-molecule drug causes the bacterium of paddy bacterial disease to achieve the purpose that prevention as killing.However, at present can be effective
The fungicide of prevention paddy bacterial disease is simultaneously few, and since bacterium easy tos produce drug resistance so that chemical prevention field
In fungicide have the shortcomings that be difficult to long-acting prevention.For this purpose, the killing of exploitation newly causes the bacterium of paddy bacterial disease
Fungicide always is what the field was badly in need of.
Invention content
Novel there is the bacterium bactericidal effect that causes paddy bacterial disease the purpose of the present invention is to provide a kind of
Fungicide provides application of the triazole sulfonates compounds in preventing paddy bacterial disease.
To achieve the goals above, one aspect of the present invention provides a kind of method for disinfection for the bacterium causing rice disease, should
Method includes contacting triazole sulfonates compounds with the bacterium of rice disease is caused, wherein the triazole sulphur
Acid esters compound is one or more in formula (1) compound represented：
Formula (1)
Wherein, L1For the phenylene being optionally substituted with a substituent, the biphenylene being optionally substituted with a substituent or optional quilt
The naphthylene of substituent group substitution；Each R1It is each independently selected from the alkyl of C1-C6；R2For the C6- being optionally substituted with a substituent
The heteroaryl of the aryl of C20 or the C5-C20 being optionally substituted with a substituent, each substituent group are each independently selected from cyano, halogen
The C1-C6's that alkyl, the cyano for the C1-C6 that alkyl, the phenyl for the C1-C6 that element, the alkyl of C1-C6, halogen replace replace replace
The alkoxy for the C1-C6 that alkyl, the alkoxy of C1-C6, phenyl replace, the alkoxy of the C1-C6 of halogen substitution and cyano substitution
C1-C6 alkoxy.
A kind of method of prevention paddy bacterial disease of second aspect of the present invention, this method includes by triazole sulfonic acid esters
Compound is applied to rice plant, wherein the triazole sulfonates compounds are one kind in formula (1) compound represented
Or it is a variety of：
Formula (1)
Wherein, L1For the phenylene being optionally substituted with a substituent, the biphenylene being optionally substituted with a substituent or optional quilt
The naphthylene of substituent group substitution；Each R1It is each independently selected from the alkyl of C1-C6；R2For the C6- being optionally substituted with a substituent
The heteroaryl of the aryl of C20 or the C5-C20 being optionally substituted with a substituent, each substituent group are each independently selected from cyano, halogen
The C1-C6's that alkyl, the cyano for the C1-C6 that alkyl, the phenyl for the C1-C6 that element, the alkyl of C1-C6, halogen replace replace replace
The alkoxy for the C1-C6 that alkyl, the alkoxy of C1-C6, phenyl replace, the alkoxy of the C1-C6 of halogen substitution and cyano substitution
C1-C6 alkoxy.
Third aspect present invention provides a kind of triazole sulfonates compounds conduct in prevention paddy bacterial disease
The application of fungicide, wherein the triazole sulfonates compounds are one or more in formula (1) compound represented：
Formula (1)
Wherein, L1For the phenylene being optionally substituted with a substituent, the biphenylene being optionally substituted with a substituent or optional quilt
The naphthylene of substituent group substitution；Each R1It is each independently selected from the alkyl of C1-C6；R2For the C6- being optionally substituted with a substituent
The heteroaryl of the aryl of C20 or the C5-C20 being optionally substituted with a substituent, each substituent group are each independently selected from cyano, halogen
The C1-C6's that alkyl, the cyano for the C1-C6 that alkyl, the phenyl for the C1-C6 that element, the alkyl of C1-C6, halogen replace replace replace
The alkoxy for the C1-C6 that alkyl, the alkoxy of C1-C6, phenyl replace, the alkoxy of the C1-C6 of halogen substitution and cyano substitution
C1-C6 alkoxy.
Triazole sulfonates compounds provided by the invention are to causing the bacterium of rice disease that there is effective sterilization to make
With, can as fungicide prevention paddy bacterial disease on obtain excellent effect.
Specific implementation mode
The endpoint of disclosed range and any value are not limited to the accurate range or value herein, these ranges or
Value should be understood as comprising the value close to these ranges or value.For numberical range, between the endpoint value of each range, respectively
It can be combined with each other between the endpoint value of a range and individual point value, and individually between point value and obtain one or more
New numberical range, these numberical ranges should be considered as specific open herein.
In the present invention, such as groupIn dotted line indicate connecting key, that specify on the group with its
The site of its group connection.
One aspect of the present invention provides a kind of method for disinfection for the bacterium causing rice disease, and this method includes by triazole sulphur
Acid esters compound is contacted with the bacterium of rice disease is caused, wherein the triazole sulfonates compounds are formula (1)
It is one or more in compound represented：
Formula (1)
Wherein, L1For the phenylene being optionally substituted with a substituent, the biphenylene being optionally substituted with a substituent or optional quilt
The naphthylene of substituent group substitution；Each R1It is each independently selected from the alkyl of C1-C6；R2For the C6- being optionally substituted with a substituent
The heteroaryl of the aryl of C20 or the C5-C20 being optionally substituted with a substituent, each substituent group are each independently selected from cyano, halogen
The C1-C6's that alkyl, the cyano for the C1-C6 that alkyl, the phenyl for the C1-C6 that element, the alkyl of C1-C6, halogen replace replace replace
The alkoxy for the C1-C6 that alkyl, the alkoxy of C1-C6, phenyl replace, the alkoxy of the C1-C6 of halogen substitution and cyano substitution
C1-C6 alkoxy.
In the present invention, the specific example of the alkyl of C1-C6 for example may include：Methyl, ethyl, n-propyl, isopropyl,
Normal-butyl, sec-butyl, tertiary butyl, n-pentyl, n-hexyl etc..The narrower such group of carbon atom number can also met certainly
Body is properly selected under limiting from above-mentioned specific group.
In the present invention, the specific example of halogen for example may include：F, Cl, Br, I etc..
In the present invention, the specific example of the alkyl of the C1-C6 of halogen substitution for example may include：-CF3、-CCl3、-
CBr3、-CH2CF3、-CH2CCl3、-CH2CBr3、-CH2CH2CF3、-CH2CH2CH2CF3Deng.For the narrower such base of carbon atom number
Group is properly selected under can also being limited meeting itself from above-mentioned specific group.
In the present invention, the specific example of the alkyl of the C1-C6 of phenyl substitution for example may include：Benzyl, 2- phenethyls,
3- phenylpropyls, 4- benzene butyl etc..From above-mentioned tool under can also being limited meeting itself for the narrower such group of carbon atom number
It is properly selected in body group.
In the present invention, the specific example of the alkyl of the C1-C6 of cyano substitution for example may include：-CH2CN、-
CH2CH2CN、-CH2CH2CH2CN、-CH2CH2CH2CH2CN etc..The narrower such group of carbon atom number can also met certainly
Body is properly selected under limiting from above-mentioned specific group.
In the present invention, the specific example of the alkoxy of C1-C6 for example may include：Methoxyl group, ethyoxyl, positive third oxygen
Base, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy, n-pentyloxy, positive hexyloxy etc..It is narrower for carbon atom number
Such group is properly selected under can also being limited meeting itself from above-mentioned specific group.
In the present invention, the specific example of the alkoxy of the C1-C6 of phenyl substitution for example may include：Benzyloxy, 2- benzene
Ethyoxyl, 3- phenylpropyl alcohols oxygroup, 4- benzene butoxy etc..The narrower such group of carbon atom number can also be limited meeting itself
Under properly selected from above-mentioned specific group.
In the present invention, the specific example of the alkoxy of the C1-C6 of halogen substitution for example may include：-OCF3、-
OCCl3、-OCBr3、-OCH2CF3、-OCH2CCl3、-OCH2CBr3、-OCH2CH2CF3、-OCH2CH2CH2CF3Deng.For carbon atom
The narrower such group of number is properly selected under can also being limited meeting itself from above-mentioned specific group.
In the present invention, the specific example of the alkoxy of the C1-C6 of cyano substitution for example may include：-OCH2CN、-
OCH2CH2CN、-OCH2CH2CH2CN、-OCH2CH2CH2CH2CN etc..It can also be full for the narrower such group of carbon atom number
Foot itself is properly selected under limiting from above-mentioned specific group.
According to the present invention, wherein the specific example of the phenylene being optionally substituted with a substituent for example can be following formula
Shown in one kind in structure：
Wherein, R3It can be single-point substitution, can also be multiple spot substitution, work as R3When replacing for multiple spot, each R3It can phase
Together, it can also be different, for this purpose, each R3It is each independently selected from the C1- that H, cyano, halogen, the alkyl of C1-C6, halogen replace
The alkyl of C6, the alkyl of C1-C6 of phenyl substitution, the alkyl of C1-C6 of cyano substitution, the alkoxy of C1-C6, phenyl replace
It is one or more in the alkoxy of the C1-C6 of the alkoxy of C1-C6, the alkoxy of the C1-C6 of halogen substitution and cyano substitution.
It should be understood that the description hereinafter to substituent group is readily applicable to R3For group.
According to the present invention, wherein the specific example for the biphenylene being optionally substituted with a substituent can be for example following formula institute
One kind in the structure shown：
Wherein R3As defined above
, the R that can also be described above in this group3It is respectively selected independently in group range.
According to the present invention, wherein the specific example for the naphthylene being optionally substituted with a substituent for example can be shown in following formula
Structure in one kind：
Wherein R3As defined above, exist
The R that can also be described above in this group3It is respectively selected independently in group range.
In the case of, according to the invention it is preferred to, L1For the phenylene being optionally substituted with a substituent；Each R1It selects each independently
From the alkyl of C1-C4；R2For the aryl of C6-C14 being optionally substituted with a substituent or the C5-C15 being optionally substituted with a substituent
Heteroaryl, each substituent group are each independently selected from alkyl, the benzene for the C1-C4 that cyano, halogen, the alkyl of C1-C4, halogen replace
The alcoxyl for the C1-C4 that the alkyl of the C1-C4 of base substitution, the alkyl of C1-C4 of cyano substitution, the alkoxy of C1-C4, phenyl replace
The alkoxy of the alkoxy for the C1-C4 that base, halogen replace and the C1-C4 of cyano substitution.
Preferably, L1For the phenylene being optionally optionally substituted by halogen, the phenylene optionally replaced by cyano, optionally by C1-C4
Alkyl-substituted phenylene or the C1-C4 being optionally optionally substituted by halogen alkyl-substituted phenylene；Each R1Each independently
Alkyl selected from C1-C4；R2It is substituted for the phenyl being optionally substituted with a substituent, the naphthalene being optionally substituted with a substituent or optionally
The pyridyl group of base substitution, each substituent group are each independently selected from the C1-C4 that cyano, halogen, the alkyl of C1-C4, halogen replace
Alkyl, phenyl substitution C1-C4 alkyl, cyano substitution the alkyl of C1-C4, the alkoxy of C1-C4, phenyl substitution
The alkoxy of the C1-C4 of the alkoxy of C1-C4, the alkoxy of the C1-C4 of halogen substitution and cyano substitution.
It is highly preferred that L1For the phenylene being optionally optionally substituted by halogen；Each R1It is each independently selected from methyl, ethyl, positive third
Base, isopropyl and normal-butyl；R2It is taken for the phenyl being optionally substituted with a substituent, the naphthalene being optionally substituted with a substituent or optionally
For the pyridyl group of base substitution, each substituent group is each independently selected from cyano, F, Cl, Br, I, methyl, ethyl, n-propyl, isopropyl
Base, normal-butyl ,-CF3, benzyl ,-CH2CN、-CH2CH2CN, methoxyl group, ethyoxyl, positive propoxy, isopropoxy, n-butoxy,
Benzyloxy ,-OCF3、-OCH2CF3、-OCH2CN and-OCH2CH2CN。
In a kind of preferred embodiment of the present invention, L1For one kind in structure shown in following formula：
In a kind of preferred embodiment of the present invention, R2For one kind in structure shown in following formula：
In a kind of preferred embodiment of the present invention, L1ForWhen, R2For the virtue of the C6-C20 of cyano substitution
The virtue of the aryl for the C6-C20 that aryl, the F for the C6-C20 that base, ortho position list Br replace replace, the alkyl-substituted C6-C20 of C1-C4
The aryl of base, the aryl of alkyl-substituted C6-C20 of at least one Cl and at least one C1-C4, pyridyl group or C6-C20.
In a kind of preferred embodiment of the present invention, L1ForWhen, R2For the C6-C20 of at least two Cl substitutions
Aryl, at least one trifluoromethyl and at least one Cl substitution C6-C20 aryl, pyridyl group or phenyl.
In a kind of preferred embodiment of the present invention, L1ForWhen, R2For at least one trifluoromethyl and extremely
The aryl of the C6-C20 of few Cl substitutions.
In a kind of preferred embodiment of the present invention, L1ForWhen, R2For at least one trifluoromethyl and
The aryl of the C6-C20 of at least one Cl substitutions, the aryl of the C6-C20 of at least two Cl substitutions, at least two Cl (two or three
It is a or more) heteroaryl of substituted C5-C20 or the C6- of at least two F (two, three etc., especially perfluor) substitutions
The aryl of C20.
In a kind of preferred embodiment of the present invention, L1ForWhen, R2For the aryl of unsubstituted C6-C20.
In a kind of preferred embodiment of the present invention, L1ForWhen, R2For at least one Cl and at least
The heteroaryl of the aryl of the C6-C20 of one Br substitutions, the C5-C20 of at least one (such as one, two, three etc.) Cl substitutions
Or the heteroaryl of at least one trifluoromethyl and the C5-C20 of at least one Cl substitutions.
In a kind of preferred embodiment of the present invention, L1ForWhen, R2For the aryl or at least of C6-C20
The heteroaryl of the C5-C20 of one (such as one, two, three etc.) Cl substitutions.
In a kind of preferred embodiment of the present invention, L1ForWhen, R2For the aryl of C6-C20.
Preferably, the triazole sulfonates compounds are one or more in compound shown in following formula；
According to the present invention, formula 1-1, formula 1-2 in above-mentioned formula, formula 1-9, formula 1-15, formula 1-18, formula 1-19, formula 1-21, formula
1-22, formula 1-24, formula 1-25, formula 1-26, formula 1-27, formula 1-29, formula 1-32, formula 1-33, formula 1-35, formula 1-41, formula 1-42, formula
1-43, formula 1-44, formula 1-45, formula 1-46 and formula 1-47 to cause rice disease bacterium have more outstanding inhibitory activity,
There is higher potential value in prevention paddy bacterial disease, most preferably, formula 1-1, formula 1-2, formula 1-15, formula 1-
24, formula 1-26, formula 1-27, formula 1-35, formula 1-41, formula 1-42, formula 1-43, formula 1-46, formula 1-18, formula 1-21, formula 1-22, formula 1-
25, formula 1-29, formula 1-33, formula 1-44, formula 1-45 and formula 1-47 have better paddy bacterial disease-controlling effect.
According to the present invention, the side of this field routine may be used in triazole sulfonates compounds shown in above-mentioned formula (1)
Method synthesizes to obtain, it is preferable that the preparation method of triazole sulfonates compounds shown in above-mentioned formula (1) includes：
(1) in the presence of alkali compounds, formula (2) compound represented and formula (3) compound represented are etherified
Reaction, obtains formula (4) compound represented, formula (2) R2-OH；Formula (3) X-L1-NO2, X is halogen (preferably F)；Formula (4) R2-
O-L1-NO2；
(2) in the presence of catalytic hydrogenation catalyst, formula (4) compound represented is subjected to catalytic hydrogenation, obtains formula
(5) compound represented, formula (5) R2-O-L1-NH2；
(3) formula (5) compound represented is carried out that formula (6) compound represented, formula (6) R is obtained by the reaction2-O-L1-OH；
(4) formula (6) compound represented and formula (7) compound represented are subjected to esterification, obtained shown in formula (1)
Compound, formula (7)X ' is halogen (preferably Cl).
Wherein, each group in the above method can be properly selected according to associated description above, can be with
It is properly selected according to the target compound of required synthesis.
According to the present invention, in step (1), the dosage of formula (2) compound represented and formula (3) compound represented can be
Variation in wider range, it is preferable that the mole dosage ratio of formula (2) compound represented and formula (3) compound represented is 1-2：
1, preferably 1.01-1.5：1, more preferably 1.05-1.2：1.
Wherein, the alkali compounds can be potassium carbonate, sodium carbonate, sodium bicarbonate, sodium hydroxide, potassium hydroxide, hydrogen
It is one or more in lithia etc..Preferably, the alkali compounds and the mole dosage ratio of formula (3) compound represented are
0.6-4：1, preferably 1-2：1 more preferably 1.1-1.6：1.
Wherein, the etherification reaction described in step (1) carries out in the first organic solvent, and first organic solvent can be with
Organic solvent in the etherification reaction carried out conventionally used for alcohol compound and halogenated hydrocarbons for this field, it is preferable that described first
Organic solvent is dichloromethane, chloroform, tetrahydrofuran, N, N '-dimethyl formamide (DMF) and dimethyl sulfoxide (DMSO) (DMSO)
In it is one or more.The dosage of the organic solvent can change in wider range, such as relative to formula (2) institute of 1mmol
The dosage of total dosage of the compound and formula (3) compound represented shown, first organic solvent is 2-10mL, preferably 2-
5mL。
Wherein, under preferable case, the condition of the etherification reaction includes：Temperature is -10 DEG C to 100 DEG C (preferably 20-80
DEG C, more preferably 40-80 DEG C), the time is 0.5-48h (preferably 2-12h, more preferably 6-12h).The reaction can also be lazy
Carried out in property atmosphere, the inert atmosphere such as can by nitrogen, helium, neon, argon gas in one or more offers.
Wherein, in order to extract formula (4) compound represented, which can also include by the ether
The product cooling of change reaction is fallen back in (especially ice water), and precipitation can be precipitated, be then separated by solid-liquid separation, gained solid phase is
Formula (4) compound represented.
According to the present invention, the nitro in formula (4) compound represented can be reduced to amido by the catalytic hydrogenation
To obtain formula (5) compound represented.Catalytic hydrogenation catalyst used by the catalytic hydrogenation is that this field is conventional
Catalytic hydrogenation used by catalyst, there is no particular limitation to this by the present invention, such as can be that (such as Pd contains Pd/C
Amount is the Pd/C of 10 weight %, is expressed as 10%Pd/C), palladium black, palladium dydroxide, palladium, palladium bichloride, platinum oxide and platinum black etc.
In it is one or more.Used hydrogen source is such as can be hydrogen, sodium borohydride, ammonium formate, cyclohexene or cyclohexadiene.
Preferably, which uses Pd/C/H2The combination of such catalyst and hydrogen.Wherein, the catalytic hydrogenation is urged
The dosage of agent can be used for the dosage that catalytic hydrogenation routinely uses for this field, and the present invention has no this special limit
It is fixed, such as on the basis of the dosage of formula (4) compound represented, the dosage of the catalytic hydrogenation catalyst is 1-20 weight %.
Wherein it is preferred to which in step (2), the condition of the catalytic hydrogenation includes：Temperature is 15-30 DEG C, and the time is
10-60min.The reaction can carry out in a second organic solvent, it is preferable that second organic solvent is dichloromethane, three
It is one or more in chloromethanes, tetrahydrofuran, methanol, ethyl alcohol, ethylene glycol and propylene glycol.The dosage of second organic solvent can
To be changed in wider range, such as relative to formula (4) compound represented of 1mmol, the dosage of second organic solvent
For 3-10mL.In order to extract formula (5) compound represented, which can also include by the catalytic hydrogenation
Product is filtered, and the solvent of filtrate is removed, you can suitably obtains formula (5) compound represented.
Formula (5) compound represented carried out according to the present invention, in step (3) formula (6) compound represented is obtained by the reaction
The various modes of this field routine may be used to realize, there is no particular limitation although the present invention is to this, it is preferable that should
Following reaction process may be used by the process of formula (5) compound represented formula (6) compound represented in step (3)：
(a) in acid condition, formula (5) compound represented and nitrous acid or its salt are subjected to diazo-reaction；
(b) product of the diazo-reaction is reacted with fluoboric acid, obtains diazonium tetrafluoroborate precipitation；
(c) in third organic solvent, diazonium tetrafluoroborate is precipitated and carries out schiemann reaction；
(d) after removing the solvent of product of the schiemann reaction, under alkaline condition, products therefrom replace anti-
It answers, obtains formula (6) compound represented.
According to the present invention, wherein in step (a), the nitrous acid or its salt for example can be nitrous acid, sodium nitrite,
It is one or more in potassium nitrite etc..Formula (5) compound represented and the molar ratio of the dosage of nitrous acid or its salt such as may be used
Think 1：1-2.The acid condition can for example be provided by organic acid solvent and/or inorganic acid aqueous solution, wherein the organic acid
Solvent is preferably that glacial acetic acid etc. (relative to formula (5) compound represented of 1mmol, for example may be used by the dosage of the organic acid solvent
Think 5-15mL).The inorganic acid aqueous solution (equivalent concentration for example can be 1-5N) is preferably that aqueous hydrochloric acid solution, sulfuric acid are water-soluble
Liquid etc. (relative to formula (5) compound represented of 1mmol, the dosage of the inorganic acid for example can be 1-30mmol).This is heavy
The condition of nitridation reaction is preferably：Temperature is -10 DEG C to 5 DEG C, time 0.5-10h.Formula can be obtained from there through step (a)
(5)-the NH of compound represented2Form the compound of diazol.
According to the present invention, in step (b), relative to formula (5) compound represented of 1mmol, the dosage of fluoboric acid is 1-
5mmol.Wherein, the fluoboric acid can be provided in the form of its aqueous solution, and the fluoboric acid of for example, 20-40 weight % is water-soluble
Liquid.Preferably, the reaction condition in step (b) includes：Temperature is 60-100 DEG C, time 2-6h.Just from there through step (b)
Diazol that can be obtained by step (a) is changed into its diazonium tetrafluoroborate precipitation.
According to the present invention, in step (c), after diazonium tetrafluoroborate precipitation is extracted, the side of heating can be passed through
The schiemann reaction occurs for formula, thus obtains corresponding F for product.Wherein, the third organic solvent for example can be acetic acid
Acid anhydride etc..Relative to formula (5) compound represented of 1mmol, the dosage of the third organic solvent for example can be 5-15mL.It should
The condition of schiemann reaction preferably includes：Temperature is 90-120 DEG C, time 2-6h.
According to the present invention, in step (d), after removing the solvent of product of the schiemann reaction, the fluoro product of gained
Hydroxyl substitution reaction can occur under alkaline condition, obtain formula (6) compound represented.Wherein, the alkaline condition can be with
It is provided by the aqueous solution of alkali compounds, for example, sodium hydrate aqueous solution, potassium hydroxide aqueous solution, lithium hydroxide aqueous solution etc.
In it is one or more, concentration for example can be 20-50 weight %.Relative to formula (5) compound represented of 1mmol, institute
The dosage for stating the aqueous solution of alkali compounds for example can be 2-6mL.The reaction can be conventionally used as hydroxyl substitution in this field
It carries out, such as can be carried out in methanol, ethyl alcohol, ethylene glycol, propylene glycol equal solvent in solvent employed in reaction, relative to
The dosage of formula (5) compound represented of 1mmol, the solvent for example can be 6-20mL.Preferably, the item of the substitution reaction
Part includes：Back flow reaction 0.5-6h.In order to extract formula (6) compound represented, which can also include will
The product acid of the substitution reaction (such as can be aqueous hydrochloric acid solution, aqueous sulfuric acid etc., equivalent concentration for example can be 1-
PH to 5-7 4N) is adjusted, is then extracted with organic solvent (such as ethyl acetate), saturated common salt water washing, anhydrous sodium sulfate
It is dry, filtering, precipitation simultaneously column chromatography purifying, you can obtain formula (6) compound represented.
According to the present invention, in above-mentioned steps (4), the dosage of formula (6) compound represented and formula (7) compound represented can
To be changed in wider range, as long as formula (1) compound represented of the present invention can be obtained, it is preferable that shown in formula (6)
The mole dosage ratio of compound and formula (7) compound represented is 1：0.5-2, preferably 1：0.9-1.8, more preferably 1：1-
1.5.Wherein, which exists in alkali compounds and carries out, which is preferably NaH, LiAlH4, potassium hydroxide and hydrogen
It is one or more in sodium oxide molybdena etc..Preferably, the mole dosage ratio of formula (6) compound represented and the alkali compounds is
1：0.5-2, preferably 1：1-1.8 more preferably 1：1-1.5.
Wherein, which can be in the solvent for the esterification that the halogenated sulphonyl of this field routine is carried out with alcohol
It carries out, which for example can be in glycol dimethyl ether (DME), ethylene glycol diethyl ether, THF, dichloromethane and chloroform
It is one or more.The total amount of formula (6) compound represented and formula (7) compound represented relative to 1mmol, the solvent
Dosage is preferably 5-50mL.
Preferably, the condition of the esterification includes：Temperature is 10-30 DEG C, time 1-10h.In order to by formula
(1) compound represented extracts, the step can also include the product of the esterification is quenched (for example, by using
Water is quenched), and extracted (for example, by using dichloromethane, ethyl acetate etc.) using organic solvent, dry organic phase, and
It purifies to obtain formula (1) compound represented using column chromatography.
According to the present invention, the bacterium for causing rice disease, which can be that this field is various, causes paddy bacterial disease
Bacterium, it is preferable that the compound of the present invention more has the bactericidal effect of rice leaf spot bacteria or X. c. pv. oryzicola germ
Effect.
A kind of method of prevention paddy bacterial disease of second aspect of the present invention, this method includes by triazole sulfonic acid esters
Compound is applied to rice plant, wherein the triazole sulfonates compounds are one kind in formula (1) compound represented
Or it is a variety of：
Formula (1)
Wherein, L1For the phenylene being optionally substituted with a substituent, the biphenylene being optionally substituted with a substituent or optional quilt
The naphthylene of substituent group substitution；Each R1It is each independently selected from the alkyl of C1-C6；R2For the C6- being optionally substituted with a substituent
The heteroaryl of the aryl of C20 or the C5-C20 being optionally substituted with a substituent, each substituent group are each independently selected from cyano, halogen
The C1-C6's that alkyl, the cyano for the C1-C6 that alkyl, the phenyl for the C1-C6 that element, the alkyl of C1-C6, halogen replace replace replace
The alkoxy for the C1-C6 that alkyl, the alkoxy of C1-C6, phenyl replace, the alkoxy of the C1-C6 of halogen substitution and cyano substitution
C1-C6 alkoxy.
Wherein, formula (1) compound represented is as described above, and details are not described herein the present invention.
Wherein, the method for application for triazole sulfonates compounds being applied to rice plant can be that this field is conventional
Mode, there is no particular limitation to this by the present invention.The triazole sulfonates compounds of the present invention not only can be killed effectively
Germ on rice plant, and can be long when protect rice plant no longer to infect germ.
According to the present invention, the paddy bacterial disease can be the various paddy bacterial diseases in this field, it is preferable that this
The compound of invention has more excellent effect for prevention bacterial blight of rice or X. c. pv. oryzicola.
Third aspect present invention provides a kind of triazole sulfonates compounds conduct in prevention paddy bacterial disease
The application of fungicide, wherein the triazole sulfonates compounds are one or more in formula (1) compound represented：
Formula (1)
Wherein, L1For the phenylene being optionally substituted with a substituent, the biphenylene being optionally substituted with a substituent or optional quilt
The naphthylene of substituent group substitution；Each R1It is each independently selected from the alkyl of C1-C6；R2For the C6- being optionally substituted with a substituent
The heteroaryl of the aryl of C20 or the C5-C20 being optionally substituted with a substituent, each substituent group are each independently selected from cyano, halogen
The C1-C6's that alkyl, the cyano for the C1-C6 that alkyl, the phenyl for the C1-C6 that element, the alkyl of C1-C6, halogen replace replace replace
The alkoxy for the C1-C6 that alkyl, the alkoxy of C1-C6, phenyl replace, the alkoxy of the C1-C6 of halogen substitution and cyano substitution
C1-C6 alkoxy.
Wherein, formula (1) compound represented is as described above, and details are not described herein the present invention.
According to the present invention, the paddy bacterial disease can be the various paddy bacterial diseases in this field, it is preferable that this
The compound of invention has more excellent effect for prevention bacterial blight of rice or X. c. pv. oryzicola.
The present invention will be described in detail by way of examples below.
Preparation example 1
This preparation example is used to illustrate the preparation method of the triazole sulfonates compounds of the present invention.
(1) under nitrogen protection, by 1.0mmol p-fluoronitrobenzenes, the 2- cyanophenols of 1.1mmol and 1.5mmol K2CO3
It is added into the DMF of 5mL and oil bath (60 DEG C of oil bath temperature) is reacted 8 hours, TLC monitors reaction process.After reaction, by body
System is cooled to room temperature, and pours into ice water, occurs largely precipitating, after stratification, intermediate 2 '-cyano-benzene oxygen-is obtained by filtration
4- nitrobenzenes.
(2) the 2 ' of 5mmol-cyano-benzene oxygen -4- nitrobenzenes are dissolved in a certain amount of dichloromethane and (are usually
25mL), 10%Pd-C (it is 15% that 2 '-cyano-benzene oxygen -4- nitrobenzene weight are added that Pd-C weight, which is added) is added, is passed through
H2, TLC monitoring reaction process, the reaction 30 minutes of (about 25 DEG C) of room temperature, after reaction, filtrate is sloughed solvent and obtained by filtering
Crude product, column chromatography obtain intermediate 2 '-cyano-benzene oxygen -4- aniline.
(3) under nitrogen protection, the 2 ' of 0.4mmol-cyano-benzene oxygen -4- aniline are dissolved in the glacial acetic acid of 3mL, then
It is to slowly warm up to 50-55 DEG C, after solution is clarified, the hydrochloric acid solution of the 2N of 3.5mL is slowly added dropwise, is added dropwise, in ice bath item
The sodium nitrite solution 3mL of 2N is added under part, until after reaction mixture clarification, the fluoborate solution 1mL of 38 weight % is added, so
It is reacted 4 hours under conditions of 80 DEG C afterwards.After reaction, system is cooled to room temperature, there is a large amount of precipitation to generate, will mixes
Object filters, and filter residue is dissolved in the acetic anhydride of 3mL under conditions of nitrogen protection, then heats to 110 DEG C, reacts 3h, will be excessive
Acetic anhydride be removed under reduced pressure, 45 weight %NaOH solution of 4mL ethyl alcohol and 1mL are then added, heating reflux reaction 2 hours adds
The hydrochloric acid for entering 2N adjusts pH=6 or so, and last ethyl acetate extracts, saturated common salt water washing, anhydrous sodium sulfate drying, filtering,
Precipitation obtains crude product, and column chromatography purifies to obtain intermediate 2 '-cyano-benzene oxygen -4- phenol.
(4) 0.1mmol intermediates 2 '-cyano-benzene oxygen -4- phenol and 0.2mmol NaH (purity is 60 weight %) are existed
1h is stirred in the DME of 3mL dryings, under condition of ice bath, is slowly added dropwise dissolved with 0.1mmol intermediates 1- (N, N- dimethyl sulphonyl
Base) -1H-1, the DME mixed solutions of the 3mL of 2,4- triazole -3- sulfonic acid chlorides are added dropwise, anti-under the conditions of room temperature (about 25 DEG C)
Should completely after, a small amount of water quenching is added and goes out reaction, dichloromethane extraction, organic phase is dried with anhydrous sodium sulfate, and column chromatography purifies
Formula 1-1 compounds represented are obtained, Structural Identification is shown in Table 1.
Preparation example 2-51
This preparation example is used to illustrate the preparation method of the triazole sulfonates compounds of the present invention.
According to the method described in preparation example 1, the compound listed by table 1 is prepared, the Structural Identification of these compounds is shown in Table 1 institute
Show, but in preparation process, with preparation example 1 it is different be：
Preparation example 2：2- cyanophenols are replaced using 4- cyanophenols in step (1)；
Preparation example 3：2- cyanophenols are replaced using 2- metoxyphenols in step (1)；
Preparation example 4：2- cyanophenols are replaced using the bromo- 5- fluorophenols of 2- in step (1)；
Preparation example 5：2- cyanophenols are replaced using 2,6- dichloro- phenol in step (1)；
Preparation example 6：2- cyanophenols are replaced using the chloro- 4- trifloro methyl phenols of 2- in step (1)；
Preparation example 7：2- cyanophenols are replaced using 2,6- difluoro-benzene phenol in step (1)；
Preparation example 8：2- cyanophenols are replaced using 2- chlorophenols in step (1)；
Preparation example 9：2- cyanophenols are replaced using 2- bromophenols in step (1)；
Preparation example 10：2- cyanophenols are replaced using 4- benzyloxy phenols in step (1)；
Preparation example 11：2- cyanophenols are replaced using 4- bromophenols in step (1)；
Preparation example 12：2- cyanophenols are replaced using the fluoro- 4- trifloro methyl phenols of 2- in step (1)；
Preparation example 13：2- cyanophenols are replaced using 2- fluorophenols in step (1)；
Preparation example 14：2- cyanophenols are replaced using 3- methylphenols in step (1)；
Preparation example 15：2- cyanophenols are replaced using 3- benzyloxy phenols in step (1)；
Preparation example 16：P-fluoronitrobenzene is replaced using 1,2-, bis- fluoro- 4- nitrobenzenes in step (1), 2- is replaced using phenol
Cyanophenol；
Preparation example 17：P-fluoronitrobenzene is replaced using the fluoro- 5- nitrobenzenes of the bromo- 2- of 1- in step (1), 2- is replaced using phenol
Cyanophenol；
Preparation example 18：P-fluoronitrobenzene is replaced using the fluoro- 5- nitrobenzenes of the chloro- 2- of 1- in step (1), using the bromo- 4- chlorine of 2-
Phenol replaces 2- cyanophenols；
Preparation example 19：P-fluoronitrobenzene is replaced using 1,2-, bis- fluoro- 4- nitrobenzenes in step (1), using 2- hydroxyls -3,5-
Dichloropyridine replaces 2- cyanophenols；
Preparation example 20：P-fluoronitrobenzene is replaced using the fluoro- 5- nitrobenzenes of the chloro- 2- of 1- in step (1), using the chloro- 4- of 2- tri-
Methyl fluoride phenol replaces 2- cyanophenols；
Preparation example 21：P-fluoronitrobenzene is replaced using the fluoro- 5- nitrobenzenes of the chloro- 2- of 1- in step (1), using hydroxyl -3 2-,
5- dichloropyridines replace 2- cyanophenols；
Preparation example 22：P-fluoronitrobenzene is replaced using the fluoro- 5- nitrobenzenes of the chloro- 2- of 1- in step (1), using 2- hydroxyls -3-
Chloro-5-trifluoromethylpyridine replaces 2- cyanophenols；
Preparation example 23：P-fluoronitrobenzene is replaced using 1,2-, bis- fluoro- 4- nitrobenzenes in step (1), using 2- hydroxyls -3-
Chloro-5-trifluoromethylpyridine replaces 2- cyanophenols；
Preparation example 24：2- cyanophenols are replaced using 2- methyl -4- chlorophenols in step (1)；
Preparation example 25：P-fluoronitrobenzene is replaced using 1,2-, bis- fluoro- 4- nitrobenzenes in step (1), using 2,4- dichloro-benzenes
Phenol replaces 2- cyanophenols；
Preparation example 26：P-fluoronitrobenzene is replaced using o-fluoronitrobenzene in step (1), 2- is replaced using 2,4- chlorophenesic acids
Cyanophenol；
Preparation example 27：P-fluoronitrobenzene is replaced using o-fluoronitrobenzene in step (1), using the chloro- 4- trifluoromethylbenzenes of 2-
Phenol replaces 2- cyanophenols；
Preparation example 28：P-fluoronitrobenzene is replaced using the fluoro- 5- nitrobenzenes of 1,3-, bis- chloro- 2- in step (1), it is chloro- using 2-
4- trifloro methyl phenols replace 2- cyanophenols；
Preparation example 29：P-fluoronitrobenzene is replaced using the fluoro- 5- nitrobenzenes of 1,3-, bis- chloro- 2- in step (1), using 2,4- bis-
Chlorophenol replaces 2- cyanophenols；
Preparation example 30：P-fluoronitrobenzene is replaced using the fluoro- 5- nitrobenzenes of 1,3-, bis- chloro- 2- in step (1), using 2- hydroxyls
Base -3,5- dichloropyridines replace 2- cyanophenols；
Preparation example 31：P-fluoronitrobenzene is replaced using 1,2,3- tri- fluoro- 5- nitrobenzenes in step (1), using 2,4,6- tri-
Chlorophenol replaces 2- cyanophenols；
Preparation example 32：P-fluoronitrobenzene is replaced using 1,2,3- tri- fluoro- 5- nitrobenzenes in step (1), using 2,4- dichloros
Phenol replaces 2- cyanophenols；
Preparation example 33：P-fluoronitrobenzene is replaced using the fluoro- 5- nitrobenzenes of the chloro- 2- of 1- in step (1), using 2,4- dichloro-benzenes
Phenol replaces 2- cyanophenols；
Preparation example 34：P-fluoronitrobenzene is replaced using the fluoro- 5- nitrobenzenes of 1,3-, bis- chloro- 2- in step (1), using 2- hydroxyls
Base -3- chloro-5-trifluoromethylpyridines replace 2- cyanophenols；
Preparation example 35：P-fluoronitrobenzene is replaced using the fluoro- 5- nitrobenzenes of the chloro- 2- of 1- in step (1), using 2,4,6- trichlorines
Phenol replaces 2- cyanophenols；
Preparation example 36：P-fluoronitrobenzene is replaced using 1,2-, bis- fluoro- 4- nitrobenzenes in step (1), is replaced using beta naphthal
2- cyanophenols；
Preparation example 37：P-fluoronitrobenzene is replaced using the fluoro- 5- nitrobenzenes of the chloro- 2- of 1- in step (1), is replaced using beta naphthal
2- cyanophenols；
Preparation example 38：P-fluoronitrobenzene is replaced using 1,2,3- tri- fluoro- 5- nitrobenzenes in step (1), using beta naphthal generation
For 2- cyanophenols；
Preparation example 39：2- cyanophenols are replaced using 2 hydroxy pyrimidine in step (1)；
Preparation example 40：P-fluoronitrobenzene is replaced using o-fluoronitrobenzene in step (1), 2- cyanogen is replaced using 2 hydroxy pyrimidine
Base phenol；
Preparation example 41：P-fluoronitrobenzene is replaced using the fluoro- 5- nitrobenzenes of the chloro- 2- of 1- in step (1), using the chloro- 2- naphthalenes of 3-
Phenol replaces 2- cyanophenols；
Preparation example 42：P-fluoronitrobenzene is replaced using the fluoro- 5- nitrobenzenes of 1,3-, bis- chloro- 2- in step (1), using 2,4,6-
Trichlorophenol, 2,4,6,-T replaces 2- cyanophenols；
Preparation example 43：2- cyanophenols are replaced using phenol in step (1)；
Preparation example 44：P-fluoronitrobenzene is replaced using the fluoro- 5- nitrobenzenes of 1,3-, bis- chloro- 2- in step (1), using 2,3,4,
5,6- Pentafluorophenols replace 2- cyanophenols；
Preparation example 45：Fluoronitrobenzene replaces p-fluoronitrobenzene between being used in step (1), using the chloro- 4- trifluoromethylbenzenes of 2-
Phenol replaces 2- cyanophenols；
Preparation example 46：2- cyanophenols are replaced using 2,4 dichloro phenol in step (1)；
Preparation example 47：P-fluoronitrobenzene is replaced using the chloro- 1- nitrobenzenes of the fluoro- 4- of 2- in step (1), using 2,4- dichloro-benzenes
Phenol replaces 2- cyanophenols；
Preparation example 48：Fluoronitrobenzene replaces 2- cyanophenols between being used in step (1)；
Preparation example 49：2- cyanophenols are replaced using parachlorophenol in step (1)；
Preparation example 50：2- cyanophenols are replaced using beta naphthal in step (1)；
Preparation example 51：P-fluoronitrobenzene is replaced using o-fluoronitrobenzene in step (1), 2- cyano benzene is replaced using phenol
Phenol.
Table 1
Test case 1
Dissolubility：Above compound is dissolved in solvent respectively, tests the dissolubility under 5000ppm concentration, wherein dissolving
It is then expressed as " √ ", " very poor " expression is difficult to dissolve and can not be tested, and the results are shown in Table shown in 2.
Inhibiting rate test process：In sterile 96 well culture plate, a certain amount of liquid to be measured is added in the first hole of first row,
Then it is diluted to the 8th hole successively by required extension rate, takes the rice leaf spot bacteria for being in exponential phase, uses microscopic count
The bacterial density that method is surveyed, a concentration of 10 are diluted to culture solution7-108Bacterium solution is added on 96 orifice plates by CFU/mL, adds 100 μ per hole
L, the 9th, 10 holes compare.Each gradient concentration repeats 5-8 times, after culture plate after 37 DEG C are cultivated 2.5 hours, adds bromination per hole
10 μ L of tetrazole solution, are further cultured for 1.5 hours, and 3000r/min centrifuges 10min, abandons supernatant.Finally add per hole on 96 orifice plates
200 μ l of SDS solution vibrate several minutes, after blue crystal is completely dissolved, sets and read on ELSIA instrument.
The calculation formula of inhibiting rate is：Inhibiting rate (%)=(1- sample wells OD values/control wells OD values) * 100%.As a result see
Shown in table 2.
Table 2
| Compound number | Solvent | 5000ppm dissolubilities | Primary dcreening operation concentration (ppm) | Inhibiting rate (%) |
| Formula 1-1 | Methanol | √ | 20 | 94.7 |
| Formula 1-2 | Methanol | √ | 20 | 94.3 |
| Formula 1-3 | Methanol | √ | 20 | 35.2 |
| Formula 1-4 | Methanol | √ | 20 | 19.4 |
| Formula 1-5 | Methanol | √ | 20 | 44.5 |
| Formula 1-6 | Methanol | √ | 20 | 1.54 |
| Formula 1-7 | Methanol | √ | 20 | 1.46 |
| Formula 1-8 | Methanol | √ | 20 | 23.7 |
| Formula 1-9 | Methanol | √ | 20 | 67.5 |
| Formula 1-10 | Methanol | √ | 20 | 35.5 |
| Formula 1-11 | Methanol | √ | 20 | 11.3 |
| Formula 1-12 | Methanol | √ | 20 | 21.1 |
| Formula 1-13 | Methanol | √ | 20 | 56.6 |
| Formula 1-14 | Methanol | √ | 20 | 74.5 |
| Formula 1-15 | Methanol | √ | 20 | 95.6 |
| Formula 1-16 | Methanol | √ | 20 | 45.0 |
| Formula 1-17 | Methanol | √ | 20 | 69.5 |
| Formula 1-18 | Methanol | √ | 20 | 88.9 |
| Formula 1-19 | Methanol | √ | 20 | 91.6 |
| Formula 1-20 | Methanol | √ | 20 | 34.3 |
| Formula 1-21 | Methanol | √ | 20 | 86.6 |
| Formula 1-22 | Methanol | √ | 20 | 93.7 |
| Formula 1-23 | Methanol | √ | 20 | 15.1 |
| Formula 1-24 | Methanol | √ | 20 | 91.1 |
| Formula 1-25 | Methanol | √ | 20 | 81.6 |
| Formula 1-26 | Methanol | √ | 20 | 86.6 |
| Formula 1-27 | Methanol | √ | 20 | 82.6 |
| Formula 1-28 | Methanol | √ | 20 | 58.5 |
| Formula 1-29 | Methanol | √ | 20 | 90.4 |
| Formula 1-30 | Methanol | √ | 20 | 8.7 |
| Formula 1-31 | Methanol | It is very poor | / | / |
| Formula 1-32 | Methanol | √ | 20 | 93.1 |
| Formula 1-33 | Methanol | √ | 20 | 89.4 |
| Formula 1-34 | Methanol | √ | 20 | 38.2 |
| Formula 1-35 | Methanol | √ | 20 | 84.7 |
| Formula 1-36 | Methanol | √ | 20 | 37.7 |
| Formula 1-37 | Methanol | √ | 20 | 2.2 |
| Formula 1-38 | Methanol | √ | 20 | 77.1 |
| Formula 1-39 | Methanol | √ | 20 | 59.3 |
| Formula 1-40 | Methanol | √ | 20 | 61.6 |
| Formula 1-41 | Methanol | √ | 20 | 92.5 |
| Formula 1-43 | Methanol | √ | 20 | 96.3 |
| Formula 1-44 | Methanol | √ | 20 | 92.5 |
| Formula 1-45 | Methanol | √ | 20 | 87.1 |
| Formula 1-46 | Methanol | √ | 20 | 90.7 |
| Formula 1-47 | Methanol | √ | 20 | 83.7 |
| Formula 1-48 | Methanol | √ | 20 | 18.2 |
| Formula 1-49 | Methanol | √ | 20 | 56.5 |
| Formula 1-50 | Methanol | √ | 20 | 13.8 |
| Formula 1-51 | Methanol | √ | 20 | 42.5 |
Test case 2
The higher compound of inhibiting rate in test case 1 is chosen, measures these compounds in rice leaf spot bacteria
Inhibition on EC50(μ g/mL), and with thiophene (Bismerthiazol is purchased from ZHEJIANG LONGWAN CHEMICALS Co., Ltd.) conduct pair
According to group, shown in table 3.
The test process includes：In the NA fluid nutrient mediums of 30mL, (ingredient is：Per 1000mL culture medium 10g containing sucrose, junket
Protolysate 8g, yeast extract 4g, K2HPO42g, Mg2SO4·7H2O 0.3g, agar 15g, pH 6.8-7.1) in be separately added into
A certain amount of liquid to be measured, to obtain the medicine that each medicament is respectively 25,12.5,6.25,3.125,1.562,0.5 and 0 μ g/mL
Liquid.The thallus suspension liquid 1mL that turbidity is 50 is added after sterilizing thereto respectively, often processing is repeated twice, 28 DEG C of shaken cultivations
WCY-W06 type turbidimeters are used to survey the turbidity of thallus suspension liquid afterwards for 24 hours.Drug concentration logarithm is established to bacterium by statistical method
The virulence regression equation of body growth inhibition probit value, and seek EC50。
Table 3
Test case 3
1) bacterial blight of rice live body potting protecting effect is tested：By test compound (as shown in the following table 4 and 5) and right
It is made into respectively with the Tween solution of 0.1 weight % according to medicament (the Thiodiazole-copper aqueous suspension agent of 20 weight %, the same below) a concentration of
200 μ g/mL's contains drug solns, the blade surface in rice is sprayed, until having drop to drip.After Yu Yizhou, in rice
Blade cuts off blade tip with the scissors for speckling with bacterial blight of rice pathogen at 1~2cm of blade tip, and wound in bacterium solution
10s or so is impregnated, while setting clear water control and the bacterium solution control of not adding medicine.Each 20 plants of rice seedlings of processing, after dispenser 21 days,
40 leaves are randomly selected, the scab length of rice leaf is recorded, and calculate its anti-efficiency, wherein the test knot of first batch
Fruit is shown in Table 4, and the test result of second lot is shown in Table 5：
Anti-efficiency (%)=(processing group scab length-bacterium solution group scab length)/processing group scab length * 100
Table 4
| Medicament | Concentration (μ g/mL) | Anti-efficiency (%) |
| 1-1 | 200 | 48.57 |
| 1-15 | 200 | 51.33 |
| 1-24 | 200 | 53.74 |
| 1-26 | 200 | 47.77 |
| 1-27 | 200 | 48.35 |
| 1-35 | 200 | 45.76 |
| 1-41 | 200 | 49.33 |
| 1-42 | 200 | 55.12 |
| 1-43 | 200 | 58.24 |
| 1-46 | 200 | 46.73 |
| 20% Thiodiazole-copper suspending agents | 200 | 48.39 |
It can be seen from Table 4 that under the conditions of a concentration of 200 μ g/mL, 21 days after medicine, formula 1-42, formula 1-43, formula 1-
15, formula 1-24, formula 1-41 and formula 1-1 have preferable protecting effect to bacterial blight of rice.
Table 5
| Medicament | Concentration (μ g/mL) | Anti-efficiency (%) |
| Formula 1-2 | 200 | 57.09 |
| Formula 1-18 | 200 | 44.98 |
| Formula 1-21 | 200 | 45.71 |
| Formula 1-22 | 200 | 42.33 |
| Formula 1-25 | 200 | 47.63 |
| Formula 1-29 | 200 | 38.57 |
| Formula 1-33 | 200 | 39.86 |
| Formula 1-44 | 200 | 48.54 |
| Formula 1-45 | 200 | 41.52 |
| Formula 1-47 | 200 | 49.03 |
| 20% Thiodiazole-copper suspending agents | 200 | 53.32 |
As can be seen from Table 5, under the conditions of a concentration of 200 μ g/mL, 21 days after medicine, formula 1-2, formula 1-47 and formula 1-44
There is preferable protecting effect, preventive effect to reach 57.09%, 49.03% and 48.54% and comparison medicament thiophene bacterial blight of rice
Bacterium copper preventive effect (53.32%) is suitable.
2) bacterial blight of rice live body potting therapeutic effect is tested：In rice leaf with speckling at 1~2cm of blade tip
The scissors of bacterial blight of rice pathogen cuts off blade tip, and wound is impregnated 10s or so in bacterium solution.It, will after Yu Yizhou
Test compound (as shown in the following table 6 and 7) and comparison medicament are made into a concentration of 200 μ with the Tween solution of 0.1 weight % respectively
G/mL's contains drug solns, and sprays the blade surface in rice, until having drop to drip.The clear water of not adding medicine is set simultaneously
Control and bacterium solution control.Each 20 plants of rice seedlings of processing randomly select 40 leaves, record rice leaf after dispenser 14 days
Scab length, and calculate its anti-efficiency, wherein the test result of first batch is shown in Table 6, and the test result of second lot is shown in
Shown in table 7：
Anti-efficiency (%)=(processing group scab length-bacterium solution group scab length)/processing group scab length * 100
Table 6
| Medicament | Concentration (μ g/mL) | Anti-efficiency (%) |
| Formula 1-1 | 200 | 45.32 |
| Formula 1-24 | 200 | 50.31 |
| Formula 1-26 | 200 | 43.41 |
| Formula 1-27 | 200 | 42.11 |
| Formula 1-35 | 200 | 50.28 |
| Formula 1-41 | 200 | 42.73 |
| Formula 1-42 | 200 | 52.40 |
| Formula 1-43 | 200 | 53.99 |
| Formula 1-46 | 200 | 41.77 |
| 20% Thiodiazole-copper suspending agents | 200 | 44.39 |
It can be seen from Table 6 that under the conditions of a concentration of 200 μ g/mL, 14 days after medicine, formula 1-42, formula 1-43 and formula 1-
24 pairs of bacterials blight of rice all have preferable therapeutic effect, and preventive effect is respectively 52.40%, 53.99% and 50.31%, with
Commercial References medicament Thiodiazole-copper preventive effect (50.75%) is suitable.
Table 7
| Medicament | Concentration (μ g/mL) | Anti-efficiency (%) |
| Formula 1-2 | 200 | 58.14 |
| Formula 1-15 | 200 | 50.82 |
| Formula 1-18 | 200 | 47.52 |
| Formula 1-21 | 200 | 51.33 |
| Formula 1-22 | 200 | 49.88 |
| Formula 1-25 | 200 | 48.36 |
| Formula 1-29 | 200 | 46.09 |
| Formula 1-33 | 200 | 48.43 |
| Formula 1-44 | 200 | 45.71 |
| Formula 1-45 | 200 | 49.35 |
| Formula 1-47 | 200 | 43.15 |
| 20% Thiodiazole-copper suspending agents | 200 | 50.75 |
It can be seen from Table 7 that under the conditions of a concentration of 200 μ g/mL, 14 days after medicine, formula 1-15, formula 1-2, formula 1-22
There is preferable therapeutic effect, preventive effect to reach 50.82%, 58.14%, 49.88% and bacterial blight of rice with formula 1-21
51.33% is suitable with comparison medicament Thiodiazole-copper preventive effect (50.75%).
Test case 4
Test compound and comparison medicament are tested under various concentration to the inhibiting rate of rice leaf spot bacteria：
Inhibiting rate test process：It is put into identical band rice leaf spot bacteria (a concentration of 10 in per ware6-107A/mL)
(ingredient is culture medium：Contain FeSO per 1000mL culture mediums4·7H2O 0.05g, Ca (NO3)2·4H2O0.5g, Na2HPO4·
12H2O 2.0g, peptone 5.0g, sucrose 20g, agar 15g, pH 6.8-7.1), it is then respectively adding the liquid of various concentration,
And any liquid is not added as a control group by one group, it cultivates at a suitable temperature, culture after a certain period of time, is taken out with ten
Word interior extrapolation method measures antibacterial circle diameter, and evaluates bactericidal activity with the presence or absence of inhibition zone and inhibition zone size.
The calculation formula of inhibiting rate is：(control group colony diameter-processing group colony diameter)/(control group colony diameter-bacterium
Cake diameter) × 100%.It the results are shown in Table shown in 8.
Wherein, it is formulated as the solution of the concentration of 0.5 weight % for the compound of the present invention of examination, is molten with dimethyl sulfoxide (DMSO)
Agent；The solution is added to according to specific concentration to be measured in table in test bacterium solution.
Wherein, " methylsulfonyl bacterium azoles (O) WP of 8 weight % " refer to the methylsulfonyl bacterium azoles wettable missible oil of 8 weight %, are purchased from
Guangxi rural area biochemistry Co., Ltd, it is the same below.
" methylsulfonyl bacterium azoles (S) WP of 8 weight % " refer to the methylsulfonyl bacterium azoles wettable powder of 8 weight %, are purchased from Guangxi
Rural area biochemistry Co., Ltd, it is the same below.
Table 8
The triazole sulfonates compounds that can be seen that the present invention by the data of table 8 have the excellent white leaf of rice
The inhibitory activity of blight bacterium.
Test case 5
Test compound and comparison medicament are tested under various concentration to the inhibiting rate of X. c. pv. oryzicola pathogen：
Inhibiting rate test process：It is put into identical band X. c. pv. oryzicola pathogen (a concentration of 10 in per ware6-107A/mL)
Culture medium (ingredient is：Contain FeSO per 1000mL culture mediums4·7H2O 0.05g, Ca (NO3)2·4H2O 0.5g, Na2HPO4·
12H2O 2.0g, peptone 5.0g, sucrose 20g, agar 15g, pH 6.8-7.1), it is then respectively adding the liquid of various concentration,
And any liquid is not added as a control group by one group, it cultivates at a suitable temperature, culture after a certain period of time, is taken out with ten
Word interior extrapolation method measures antibacterial circle diameter, and evaluates bactericidal activity with the presence or absence of inhibition zone and inhibition zone size.
The calculation formula of inhibiting rate is：(control group colony diameter-processing group colony diameter)/(control group colony diameter-bacterium
Cake diameter) × 100%.It the results are shown in Table shown in 9.
Wherein, it is formulated as the solution of the concentration of 0.5 weight % for the compound of the present invention of examination, is molten with dimethyl sulfoxide (DMSO)
Agent；The solution is added to according to specific concentration to be measured in table in test bacterium solution.
" 20 weight % Yekuzuos WP " refers to the wettable powder of 20 weight % Yekuzuos, limited purchased from Zhejiang Long Wan chemical industry
Company；
" 3 weight % kasugarnycin AS " refers to the aqua of 3 weight % kasugarnycin, contains day perseverance purchased from Hubei and creates biotechnology
Co., Ltd.
Table 9
The triazole sulfonates compounds that can be seen that the present invention by the data of table 9 have excellent rice slice
The inhibitory activity of sick pathogen.
The preferred embodiment of the present invention has been described above in detail, and still, the present invention is not limited thereto.In the skill of the present invention
In art conception range, technical scheme of the present invention can be carried out a variety of simple variants, including each technical characteristic with it is any its
Its suitable method is combined, and it should also be regarded as the disclosure of the present invention for these simple variants and combination, belongs to
Protection scope of the present invention.
Claims (12)
1. a kind of rice leaf spot bacteria causing rice disease and/or the method for disinfection of X. c. pv. oryzicola germ, feature exist
Include that triazole sulfonates compounds and the rice leaf spot bacteria and/or rice that cause rice disease are thin in, this method
Item disease germ is contacted, wherein the triazole sulfonates compounds are one kind or more in formula (1) compound represented
Kind：
Formula (1)
Wherein, L1For the phenylene being optionally substituted with a substituent；Each R1It is each independently selected from the alkyl of C1-C6；R2It is optional
The phenyl being substituted with a substituent, the naphthalene being optionally substituted with a substituent or the pyridyl group being optionally substituted with a substituent, each substitution
Base be each independently selected from cyano, halogen, the alkyl of C1-C6, the alkyl of C1-C6 of halogen substitution, phenyl substitution C1-C6
Alkoxy, the halogen for the C1-C6 that alkyl, the alkyl of C1-C6 of cyano substitution, the alkoxy of C1-C6, phenyl replace replace
The alkoxy of the C1-C6 of alkoxy and the cyano substitution of C1-C6.
2. according to the method described in claim 1, wherein, each R1It is each independently selected from the alkyl of C1-C4；Each substituent group
It is each independently selected from the alkane of the alkyl for the C1-C4 that cyano, halogen, the alkyl of C1-C4, halogen replace, the C1-C4 of phenyl substitution
The alkoxy for the C1-C4 that base, the alkyl of C1-C4 of cyano substitution, the alkoxy of C1-C4, phenyl replace, the C1- of halogen substitution
The alkoxy of the C1-C4 of alkoxy and the cyano substitution of C4.
3. according to the method described in claim 2, wherein, L1For the phenylene being optionally optionally substituted by halogen；Each R1Each independently
Selected from methyl, ethyl, n-propyl, isopropyl and normal-butyl；Each substituent group is each independently selected from cyano, F, Cl, Br, I, first
Base, ethyl, n-propyl, isopropyl, normal-butyl ,-CF3, benzyl ,-CH2CN、-CH2CH2CN, methoxyl group, ethyoxyl, positive third oxygen
Base, isopropoxy, n-butoxy, benzyloxy ,-OCF3、-OCH2CF3、-OCH2CN and-OCH2CH2CN。
4. according to the method described in any one of claim 1-3, wherein the triazole sulfonates compounds are following formula
It is one or more in compound represented；
5. a kind of method of prevention paddy bacterial disease, which is characterized in that this method includes by triazole sulfonic acid esters chemical combination
Object is applied to rice plant, wherein the paddy bacterial disease be bacterial blight of rice and/or X. c. pv. oryzicola, described three
Nitrogen azoles sulfonates compounds are one or more in formula (1) compound represented：
Formula (1)
Wherein, L1For the phenylene being optionally substituted with a substituent；Each R1It is each independently selected from the alkyl of C1-C6；R2It is optional
The phenyl being substituted with a substituent, the naphthalene being optionally substituted with a substituent or the pyridyl group being optionally substituted with a substituent, each substitution
Base be each independently selected from cyano, halogen, the alkyl of C1-C6, the alkyl of C1-C6 of halogen substitution, phenyl substitution C1-C6
Alkoxy, the halogen for the C1-C6 that alkyl, the alkyl of C1-C6 of cyano substitution, the alkoxy of C1-C6, phenyl replace replace
The alkoxy of the C1-C6 of alkoxy and the cyano substitution of C1-C6.
6. according to the method described in claim 5, wherein, each substituent group is each independently selected from cyano, halogen, C1-C4
Alkyl, the C1-C4 of the alkyl for the C1-C4 that alkyl, the phenyl for the C1-C4 that alkyl, halogen replace replace, the C1-C4 of cyano substitution
Alkoxy, phenyl substitution C1-C4 alkoxy, halogen substitution C1-C4 alkoxy and cyano substitution C1-C4 alkane
Oxygroup.
7. according to the method described in claim 6, wherein, L1For the phenylene being optionally optionally substituted by halogen；Each R1Each independently
Selected from methyl, ethyl, n-propyl, isopropyl and normal-butyl；Each substituent group is each independently selected from cyano, F, Cl, Br, I, first
Base, ethyl, n-propyl, isopropyl, normal-butyl ,-CF3, benzyl ,-CH2CN、-CH2CH2CN, methoxyl group, ethyoxyl, positive third oxygen
Base, isopropoxy, n-butoxy, benzyloxy ,-OCF3、-OCH2CF3、-OCH2CN and-OCH2CH2CN。
8. according to the method described in any one of claim 5-7, wherein the triazole sulfonates compounds are following formula
It is one or more in compound represented；
9. a kind of application of triazole sulfonates compounds in prevention paddy bacterial disease as fungicide, wherein institute
It is bacterial blight of rice and/or X. c. pv. oryzicola to state paddy bacterial disease, and the triazole sulfonates compounds are formula (1)
It is one or more in compound represented：
Formula (1)
Wherein, L1For the phenylene being optionally substituted with a substituent；Each R1It is each independently selected from the alkyl of C1-C6；R2It is optional
The phenyl being substituted with a substituent, the naphthalene being optionally substituted with a substituent or the pyridyl group being optionally substituted with a substituent, each substitution
Base be each independently selected from cyano, halogen, the alkyl of C1-C6, the alkyl of C1-C6 of halogen substitution, phenyl substitution C1-C6
Alkoxy, the halogen for the C1-C6 that alkyl, the alkyl of C1-C6 of cyano substitution, the alkoxy of C1-C6, phenyl replace replace
The alkoxy of the C1-C6 of alkoxy and the cyano substitution of C1-C6.
10. application according to claim 9, wherein each substituent group is each independently selected from cyano, halogen, C1-C4
Alkyl, the C1-C4 of the alkyl for the C1-C4 that alkyl, the phenyl for the C1-C4 that alkyl, halogen replace replace, the C1-C4 of cyano substitution
Alkoxy, phenyl substitution C1-C4 alkoxy, halogen substitution C1-C4 alkoxy and cyano substitution C1-C4 alkane
Oxygroup.
11. application according to claim 10, wherein L1For the phenylene being optionally optionally substituted by halogen；Each R1It is respectively independent
Ground is selected from methyl, ethyl, n-propyl, isopropyl and normal-butyl；Each substituent group be each independently selected from cyano, F, Cl, Br, I,
Methyl, ethyl, n-propyl, isopropyl, normal-butyl ,-CF3, benzyl ,-CH2CN、-CH2CH2CN, methoxyl group, ethyoxyl, positive third oxygen
Base, isopropoxy, n-butoxy, benzyloxy ,-OCF3、-OCH2CF3、-OCH2CN and-OCH2CH2CN。
12. according to the application described in any one of claim 9-11, wherein under the triazole sulfonates compounds are
It is one or more in formula compound represented；
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