CN116831132A - 20% fluorobenzoxazole sulfone water suspension and preparation method thereof - Google Patents
20% fluorobenzoxazole sulfone water suspension and preparation method thereof Download PDFInfo
- Publication number
- CN116831132A CN116831132A CN202310777028.5A CN202310777028A CN116831132A CN 116831132 A CN116831132 A CN 116831132A CN 202310777028 A CN202310777028 A CN 202310777028A CN 116831132 A CN116831132 A CN 116831132A
- Authority
- CN
- China
- Prior art keywords
- fluorobenzoxazole
- sulfone
- agent
- aqueous suspension
- suspending agent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000003457 sulfones Chemical class 0.000 title claims abstract description 95
- 239000007900 aqueous suspension Substances 0.000 title claims description 19
- 238000002360 preparation method Methods 0.000 title abstract description 15
- 239000000375 suspending agent Substances 0.000 claims abstract description 54
- 230000001580 bacterial effect Effects 0.000 claims abstract description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 27
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 13
- 241000207199 Citrus Species 0.000 claims abstract description 11
- 235000020971 citrus fruits Nutrition 0.000 claims abstract description 11
- 239000013530 defoamer Substances 0.000 claims abstract description 10
- 239000002562 thickening agent Substances 0.000 claims abstract description 10
- 239000002994 raw material Substances 0.000 claims abstract description 8
- 244000144730 Amygdalus persica Species 0.000 claims abstract description 7
- 244000241257 Cucumis melo Species 0.000 claims abstract description 7
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 claims abstract description 7
- 235000006040 Prunus persica var persica Nutrition 0.000 claims abstract description 7
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000004094 surface-active agent Substances 0.000 claims abstract description 6
- 235000007688 Lycopersicon esculentum Nutrition 0.000 claims abstract description 5
- 240000003768 Solanum lycopersicum Species 0.000 claims abstract description 5
- 239000008367 deionised water Substances 0.000 claims abstract description 3
- 229910021641 deionized water Inorganic materials 0.000 claims abstract description 3
- 235000007164 Oryza sativa Nutrition 0.000 claims description 29
- 235000009566 rice Nutrition 0.000 claims description 29
- 238000012360 testing method Methods 0.000 claims description 23
- 239000002245 particle Substances 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 16
- 239000002270 dispersing agent Substances 0.000 claims description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical group [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 10
- 241000196324 Embryophyta Species 0.000 claims description 9
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 9
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 claims description 9
- 229910052708 sodium Inorganic materials 0.000 claims description 9
- 239000011734 sodium Substances 0.000 claims description 9
- KVCGISUBCHHTDD-UHFFFAOYSA-M sodium;4-methylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1 KVCGISUBCHHTDD-UHFFFAOYSA-M 0.000 claims description 9
- 125000000129 anionic group Chemical group 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 239000002736 nonionic surfactant Substances 0.000 claims description 8
- 239000000080 wetting agent Substances 0.000 claims description 7
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 6
- 238000000227 grinding Methods 0.000 claims description 6
- 229910052710 silicon Inorganic materials 0.000 claims description 6
- 239000010703 silicon Substances 0.000 claims description 6
- HLPHHOLZSKWDAK-UHFFFAOYSA-M sodium;formaldehyde;naphthalene-1-sulfonate Chemical compound [Na+].O=C.C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HLPHHOLZSKWDAK-UHFFFAOYSA-M 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 239000000230 xanthan gum Substances 0.000 claims description 6
- 229920001285 xanthan gum Polymers 0.000 claims description 6
- 229940082509 xanthan gum Drugs 0.000 claims description 6
- 235000010493 xanthan gum Nutrition 0.000 claims description 6
- 239000002518 antifoaming agent Substances 0.000 claims description 5
- 239000011780 sodium chloride Substances 0.000 claims description 5
- 230000002528 anti-freeze Effects 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 238000010008 shearing Methods 0.000 claims description 3
- 230000009471 action Effects 0.000 claims description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 claims description 2
- 239000011268 mixed slurry Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 2
- 229920001296 polysiloxane Polymers 0.000 claims description 2
- 238000005086 pumping Methods 0.000 claims description 2
- 241000607479 Yersinia pestis Species 0.000 claims 6
- 240000007594 Oryza sativa Species 0.000 claims 4
- 241000238631 Hexapoda Species 0.000 claims 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 claims 1
- 241000894006 Bacteria Species 0.000 abstract description 24
- KHGNFPUMBJSZSM-UHFFFAOYSA-N Perforine Natural products COC1=C2CCC(O)C(CCC(C)(C)O)(OC)C2=NC2=C1C=CO2 KHGNFPUMBJSZSM-UHFFFAOYSA-N 0.000 abstract description 3
- 229930192851 perforin Natural products 0.000 abstract description 3
- 241000589771 Ralstonia solanacearum Species 0.000 abstract 1
- 239000003814 drug Substances 0.000 description 40
- 241000209094 Oryza Species 0.000 description 26
- 230000000694 effects Effects 0.000 description 20
- 239000000725 suspension Substances 0.000 description 20
- 229940079593 drug Drugs 0.000 description 19
- 238000003860 storage Methods 0.000 description 16
- 238000000354 decomposition reaction Methods 0.000 description 15
- 239000000575 pesticide Substances 0.000 description 15
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 9
- 230000000844 anti-bacterial effect Effects 0.000 description 8
- 238000012216 screening Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000002609 medium Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 239000004308 thiabendazole Substances 0.000 description 7
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 7
- 229960004546 thiabendazole Drugs 0.000 description 7
- 235000010296 thiabendazole Nutrition 0.000 description 7
- 238000009736 wetting Methods 0.000 description 7
- 208000035143 Bacterial infection Diseases 0.000 description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
- 239000012752 auxiliary agent Substances 0.000 description 6
- 239000003899 bactericide agent Substances 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 238000005338 heat storage Methods 0.000 description 6
- 239000005868 Metconazole Substances 0.000 description 5
- -1 fatty alcohol sulfate Chemical class 0.000 description 5
- XWPZUHJBOLQNMN-UHFFFAOYSA-N metconazole Chemical compound C1=NC=NN1CC1(O)C(C)(C)CCC1CC1=CC=C(Cl)C=C1 XWPZUHJBOLQNMN-UHFFFAOYSA-N 0.000 description 5
- 230000002265 prevention Effects 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000004563 wettable powder Substances 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 4
- 239000002671 adjuvant Substances 0.000 description 4
- 231100000053 low toxicity Toxicity 0.000 description 4
- 229920000417 polynaphthalene Polymers 0.000 description 4
- 238000004062 sedimentation Methods 0.000 description 4
- LYPGDCWPTHTUDO-UHFFFAOYSA-M sodium;methanesulfinate Chemical compound [Na+].CS([O-])=O LYPGDCWPTHTUDO-UHFFFAOYSA-M 0.000 description 4
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 244000061176 Nicotiana tabacum Species 0.000 description 3
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical group C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 238000005520 cutting process Methods 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 229940002612 prodrug Drugs 0.000 description 3
- 239000000651 prodrug Substances 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 239000001888 Peptone Substances 0.000 description 2
- 108010080698 Peptones Proteins 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 206010070834 Sensitisation Diseases 0.000 description 2
- 206010040880 Skin irritation Diseases 0.000 description 2
- 239000008186 active pharmaceutical agent Substances 0.000 description 2
- 231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 2
- 238000011047 acute toxicity test Methods 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 229940088679 drug related substance Drugs 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000010813 internal standard method Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000003801 milling Methods 0.000 description 2
- 238000005457 optimization Methods 0.000 description 2
- 235000019319 peptone Nutrition 0.000 description 2
- 230000000361 pesticidal effect Effects 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 230000008313 sensitization Effects 0.000 description 2
- 230000036556 skin irritation Effects 0.000 description 2
- 231100000475 skin irritation Toxicity 0.000 description 2
- 229960005322 streptomycin Drugs 0.000 description 2
- 231100000820 toxicity test Toxicity 0.000 description 2
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical class CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 1
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 1
- FKKAGFLIPSSCHT-UHFFFAOYSA-N 1-dodecoxydodecane;sulfuric acid Chemical compound OS(O)(=O)=O.CCCCCCCCCCCCOCCCCCCCCCCCC FKKAGFLIPSSCHT-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- 241000257303 Hymenoptera Species 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 241000228456 Leptosphaeria Species 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- HFCYZXMHUIHAQI-UHFFFAOYSA-N Thidiazuron Chemical compound C=1C=CC=CC=1NC(=O)NC1=CN=NS1 HFCYZXMHUIHAQI-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 229960002685 biotin Drugs 0.000 description 1
- 235000020958 biotin Nutrition 0.000 description 1
- 239000011616 biotin Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000002872 contrast media Substances 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 231100000584 environmental toxicity Toxicity 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 239000012434 nucleophilic reagent Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000033116 oxidation-reduction process Effects 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 235000019633 pungent taste Nutrition 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000041 toxicology testing Toxicity 0.000 description 1
- 229910052726 zirconium Inorganic materials 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- General Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- Dentistry (AREA)
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Toxicology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The application relates to a 20% fluorobenzoxazole sulfone water suspending agent and a preparation method thereof. The fluorobenzoxazole sulfone suspending agent comprises: 20wt% of fluorobenzoxazole sulfone and 3-12 wt% of surfactant; 0.5 to 2.5 weight percent of thickener; 2-6wt% of antifreezing agent; 0.3 to 0.5 weight percent of organosilicon defoamer and the balance of deionized water. The raw materials are subjected to wet sanding to obtain the fluorobenzoxazole sulfone suspending agent. It can be used for preventing and treating bacterial leaf blight (Xoo), bacterial leaf spot (Xoc), citrus canker (Xac), tomato bacterial wilt (r.solanacearum), peach tree perforin and melon angular bacteria.
Description
Technical Field
The application belongs to the field of pesticides, and particularly relates to a 20% fluorobenzoxazole sulfone water suspension and a preparation method thereof.
Background
Aiming at the prevention and treatment of bacterial diseases such as bacterial leaf blight of rice, rice fine strip disease, tomato bacterial wilt, citrus canker and the like, the traditional protective medicaments represented by copper preparations and antibiotics are mainly used in production, medicaments with systemic property and good therapeutic property are lacked, and a large number of potential risks such as toxic crop, excessive content of heavy metals in soil and antibiotics are used. The development of a novel non-copper bactericide product for preventing and controlling plant diseases has great value.
The fluorobenzoxazole sulfone is a novel bactericide independently created by Guizhou university and has the characteristics of high efficiency, low toxicity, low risk and the like, and the concentration (EC) of the fluorobenzoxazole sulfone in inhibiting bacterial blight bacteria, bacterial leaf spot bacteria, citrus canker bacteria, tomato bacterial wilt bacteria, peach tree perforin bacteria and melon fine angle bacteria of rice 50 ) The values are 1.07, 7.14, 1.23, 17.46, 23.52 and 44.51 mug/mL respectively, which are superior to the control drugs of thiabendazole and metconazole. The living potting test results show that: when the concentration is 200 mug/mL, the 'fluorobenzoxazole sulfone' has better treatment and protection effects on rice bacterial leaf blight, the prevention effect is 43.4 percent and 57.5 percent respectively, the control medicament is superior to that of the control medicament, namely the metconazole and the thiabendazole, and the national pesticide standardization technical commission registration named fluorobenzoxazole sulfone is obtained.
98.5% profound pharmacological properties of fluorobenzoxazole sulfone: the molecular weight 256.03 is that the raw medicine is milky white soft needle-shaped powder, has strong pungent taste, has a melting point of 106.9 ℃, is degraded before being heated to the boiling point under the air atmosphere, has no explosiveness, changes the color of the raw medicine mixed with iron powder from milky white to grey white, has no oxidation-reduction/chemical incompatibility, has no corrosiveness, has no optical rotation and is not inflammable matter for packaging materials provided by manufacturers. The original medicine is stable to light and heat, and is easy to decompose under alkaline condition (pH=10). The 1,3, 4-oxadiazole in the fluorobenzoxazole sulfone structure is an electron-deficient heterocycle, is influenced by a strong electron-withdrawing group methanesulfonyl on the 2-position, can be attacked by a nucleophilic reagent containing polar functional groups such as hydroxyl, sulfhydryl or amino, and the like, and has addition elimination reaction and desmethanesulfonyl removal.
Therefore, according to the decomposition principle of the fluorobenzoxazole sulfone, a proper auxiliary agent is screened to develop a fluorobenzoxazole sulfone suspending agent stability optimization technical formula so as to solve the problem of instability of the raw materials in the 2-year storage process.
TABLE 1 pharmacological Properties of 98.5% fluorobenzoxazole sulfone
Disclosure of Invention
In order to solve the problems, the application provides a preparation formula of a 20% fluorobenzoxazole sulfone water suspending agent which is beneficial to the stabilization of raw materials, and the preparation formula comprises 20% fluorobenzoxazole sulfone, 3-12% wetting dispersant, 0.5-2.5% wt, 2-8% wt and 0.2-0.5% wt of active ingredients, and water, wherein the weight ratio of the active ingredients is 20% wt, 3-12% wt, 0.5-2.5% wt, 2-8% wt and the water is complemented to 100% wt; the surfactant screened by the application comprises a dispersing agent or a wetting agent, is a compound of ionic or nonionic auxiliary agents, and comprises macromolecular amphiphilic anionic nonionic surfactant compounds, phosphate esters, lignin sulfonate, salts of phenolsulfonic acid or naphthalene sulfonic acid, salts of polyacrylic acid, sulfosuccinate, alkyl sulfonate, alkylaryl sulfonate, alkyl sulfate, lauryl ether sulfate, fatty alcohol sulfate, sulfonate formaldehyde condensate, sulfated hexadecyl-, heptadecyl-and stearyl alcohols and sulfated fatty alcohol glycol ether;
the defoaming agent is polydimethylsiloxane in the organic silicon defoaming agent with the weight percent of 0.3-0.5;
the antifreezing agent is inorganic salt;
the thickener is one or two of magnesium aluminum silicate SF-40 and xanthan gum.
Preferably, the dispersing agent and the wetting agent are composed of a macromolecular amphiphilic anionic non-ionic surfactant compound SC29, sodium dibenzosulfonate HAS040, naphthalene sulfonic acid sodium salt formaldehyde condensate NNO and any one of sodium paratoluenesulfonate, sodium methane sulfinate or polynaphthalene formaldehyde sulfonic acid sodium salt according to the weight ratio of 2:2:2:1.5; more preferably, the wetting dispersant consists of a macromolecular amphiphilic anionic non-ionic surfactant compound SC29, sodium dibenzosulfonate HAS040, naphthalene sulfonic acid sodium salt formaldehyde condensate NNO and sodium paratoluenesulfonate according to the weight ratio of 2:2:2:1.5.
Preferably, the thickener is 2% magnesium aluminum silicate SF-40 or 1% magnesium aluminum silicate and 0.05% xanthan gum.
The 20% fluorobenzoxazole sulfone suspending agent for preventing and treating plant bacterial diseases is prepared by taking a dispersing agent, a wetting agent, an antifreezing agent and water according to the weight percentage, stirring and dissolving, adding fluorobenzoxazole sulfone and a thickening agent according to the weight percentage, uniformly mixing under the action of a shearing machine, then pumping the mixed slurry into a sanding machine for grinding, adding an organosilicon antifoaming agent according to the weight percentage, carrying out particle size test every 1h, stopping stirring after D90 is equal to 5-8 mu m, and filtering to obtain the 20% fluorobenzoxazole sulfone suspending agent.
The application innovates: the developed dosage form is prepared by screening and formula optimization combination of wetting dispersant, and the prepared fluorobenzoxazole sulfone suspending agent has the advantages of stable performance, good water-in dispersibility and outstanding prevention effect.
1. Screening of wetting dispersants
The 20% fluorobenzoxazole sulfone suspending agent prepared by compounding the macromolecular amphiphilic anionic non-ionic surfactant compound with different types of surfactants is subjected to hot storage, and then the water dispersibility of the raw medicine and the decomposition rate of the raw medicine after hot storage are measured, and the specific results are shown in table 2.
Table 2 selection of wetting dispersants
As shown in the results of table 2, the addition of sulfonate adjuvant was found to be beneficial to the stability of the drug substance by screening for different types of adjuvant. The methylsulfonyl bacteria azole suspending agent compounded by the macromolecular amphiphilic anionic non-ionic surfactant compound SC29, sodium dibenzoyl sulfonate HAS040, naphthalene sulfonic acid sodium salt formaldehyde condensate NNO and sodium paratoluenesulfonate or sodium methane sulfinate or sodium polynaphthalene formaldehyde sulfonate HAS good dispersibility, and the decomposition rate of the original medicine after heat storage is controlled within 5%.
For the screening of the optimum amounts of the adjuvants such as sodium p-toluenesulfonate, sodium polynaphthalene formaldehyde sulfonate and sodium methane sulfinate, three contents of 0.5%, 1.5% and 3.0% were set for the screening, and the specific results are shown in Table 3.
TABLE 3 selection of adjuvant usage
As shown in the results of Table 3, the decomposition rate of fluorobenzoxazole sulfone after thermal storage was less than 10% at three different levels. Sodium methane sulfinate is relatively expensive and generally water dispersible. The suspension agent turns yellow after the sodium polynaphthalene formaldehyde sulfonate is added, and the appearance is affected. The addition of sodium paratoluenesulfonate not only can ensure good stability of the original medicine, but also is relatively cheap, and the appearance of the suspending agent is relatively better, so that the preferable wetting dispersant formula is SC 29:HOS 040:NNO:sodium paratoluenesulfonate=2:2:2:1.5 in comprehensive consideration of cost and properties.
2. Screening of thickeners
Aqueous suspending agents often suffer from storage physical stability problems such as particle agglomeration, sedimentation, water evolution, and thickening and caking. The formula is easy to generate sedimentation and water separation under long-time storage, and can improve sedimentation stability by increasing viscosity. The viscosity is too large, the product is not easy to pour, the wall hanging is serious, and the processing production and the use are difficult. Suitable viscosities provide good stability and high suspension rates for the formulation. The experiment combines the characteristic of unstable chemical property of fluorobenzoxazole sulfone according to the related theory, the auxiliary agent type needed by the formula screened in the earlier stage is not changed, the viscosity is changed by screening the amount of magnesium aluminum silicate and xanthan gum, but the increase in viscosity may decrease the autodispersibility of the aqueous suspension, thus improving the water-in dispersibility by increasing the amount of dispersant NNO. The specific results are shown in Table 4.
TABLE 4 selection of thickeners
As shown in Table 4, too much addition of xanthan gum has a certain effect on the fluidity and water dispersibility of the formulation system. Therefore, 2% of magnesium aluminum silicate is selected as a thickener or 1% of magnesium aluminum silicate is compounded with 0.05% of xanthan gum under the condition of not affecting the water-in dispersibility, so that the sedimentation stability of the suspending agent is improved, and meanwhile, the water-in dispersibility of the preparation is improved by improving the NNO content.
3. Selection of the amount of defoamer
The wetting and dispersing agent is mostly sulfonate, and a large number of bubbles can appear in the processing process to influence the grinding effect. Therefore, some organic silicon defoamer is usually added into the suspending agent, but the proper amount of defoamer is added, and the excessive addition can reduce the surface tension of the system, so that the layering phenomenon becomes more obvious. Too little addition and insignificant defoaming effect. In this test, a general purpose silicone defoamer was selected for testing, and the specific results are shown in table 5.
TABLE 5 selection of defoamer usage
As shown in Table 5, when the amount of the antifoaming agent is small, a large amount of bubbles generated during the grinding process cannot be effectively solved, and when the amount is controlled to be 0.3-0.5%, fewer bubbles are generated during the preparation process, which is beneficial to grinding.
4. Selection of antifreeze
The pesticide suspending agent using water as a dispersion medium can keep stability under the severe cold low temperature condition in the storage process, and a certain amount of proper antifreezing agent is usually required to be added. When glycerol is used as an antifreezing agent, the viscosity of the system increases and the fluidity is poor. When ethylene glycol is used as an antifreezing agent, the stability and fluidity of the preparation are good, but after thermal storage, the decomposition rate of the raw medicine is high. When sodium chloride is used as the antifreezing agent, the bottom of the antifreezing agent can be precipitated very little after cold storage, but the decomposition degree of the raw medicine can not be increased. Thus, sodium chloride was chosen as the best antifreeze.
5. Influence of particle size on the stability of the drug substance after thermal storage
After the auxiliary agent is determined, fluorobenzoxazole sulfone water suspending agents (with the number of 1-6) with different particle sizes are prepared, after thermal storage, the content of the raw pesticide is measured by adopting a pesticide thermal stability measuring method GB/T19136-2003, and then the decomposition rate of the raw pesticide after thermal storage is analyzed, wherein the specific results are shown in Table 6 and figures 2-6.
TABLE 6 influence of particle size on the stability of crude drugs
As shown in Table 6 and FIGS. 2-4, when the particle size of the 20% fluorobenzoxazole sulfone aqueous suspension prepared by using the above auxiliary agent is larger than 10 μm, the decomposition rate of the original medicine is larger and higher than 20% after thermal storage (54 ℃ + -2). When the particle size of the suspending agent raw material is 5-8 mu m, the decomposition rate is controlled between 5% and 10%, so as to meet the requirement of preparation stability. This shows that under the formula, the chemical stability of the formula and the original drug of the fluorobenzoxazole sulfone water suspending agent with the particle size has important influence, and the smaller the particle size, the better the chemical stability of the original drug, but the smaller the particle size is, and the industrial production is not easy.
6. Determination of recipe preference and preparation method
Through the experimental screening, the preferable formula and the weight ratio of the fluorobenzoxazole sulfone to the macromolecular amphiphilic anionic nonionic surfactant compound SC29 to the sodium dibenzoyl sulfonate HAS040 to the naphthalene sulfonate sodium formaldehyde condensate NNO to the sodium paratoluenesulfonate to the magnesium aluminum silicate to the organic silicon defoamer to the sodium chloride=20:2:2:2:1.5:2:0.4:4 are finally determined, and the deionized water is used for supplementing the mixture to 100 percent. Under the formulation, the ground suspending agent is favorable for the heat storage stability of the preparation.
TABLE 7 determination of preferred formulations
7.20% Fluobenzole sulfone suspending agent specification
The main properties of the suspension were tested according to the national standard requirements for pesticide suspensions (GB/T19136-2003), and are shown in Table 8. The result shows that under the formula, the fluorobenzoxazole sulfone water suspending agent is in a milky uniform dispersion system, the dispersibility and the suspension rate are good, and the decomposition rate of the original medicine after heat storage is lower than 10%.
TABLE 8 physicochemical Properties of 20% fluorobenzoxazole sulfone aqueous suspension
Drawings
FIG. 1 is a suspension study technical route;
FIG. 2 is a liquid chromatogram of a fluorobenzoxazole sulfone prodrug prior to thermal storage;
FIG. 3 is a liquid chromatogram of a fluorobenzoxazole sulfone prodrug after thermal storage;
FIG. 4 is a liquid chromatogram of a 20% fluorobenzoxazole sulfone suspension with a milled particle size D90 of 6.22 μm;
fig. 5 is a graph of therapeutic activity of 20% fluorobenzoxazole sulfone suspension and 98.6% fluorobenzoxazole sulfone prodrug against bacterial leaf blight of rice.
FIG. 6 is a graph showing the protective activity of 20% fluorobenzoxazole sulfone suspension and 98.6% fluorobenzoxazole sulfone as a raw material against bacterial leaf blight of rice;
FIG. 7 is a field test of controlling bacterial leaf blight of rice in each province;
FIG. 8 is a field test of prevention and treatment of bacterial angular leaf spot in cotton in Shandong province; wherein A:50 g/mu of fluorobenzoxazole sulfone suspending agent, B:75 g/mu of fluorobenzoxazole sulfone suspending agent, C:100 g/mu of fluorobenzoxazole sulfone suspending agent, D:250 g/mu of 72% agricultural streptomycin wettable powder;
fig. 9 is a field trial of citrus canker control in Guizhou province.
Examples
The application is further illustrated by the following examples. It should be understood that the methods described in the examples of the present application are only for illustrating the present application, and not for limiting the present application, and that simple modifications to the preparation methods of the present application under the concept of the present application are within the scope of the present application as claimed. All the starting materials and solvents used in the examples were commercially available products of the corresponding purity.
Example 1: preparation of 20% fluorobenzoxazole sulfone suspension
6.0g of sodium dibenzoyl sulfonate HAS040, 6.0g of naphthalene sulfonic acid sodium salt formaldehyde condensate NNO, 4.5g of sodium paratoluenesulfonate, 12.0g of sodium chloride and 6.0g of macromolecular amphiphilic anionic nonionic surfactant compound SC29 are weighed into a beaker containing 198.3g of secondary water, after stirring and dissolving, 60.0g of fluorobenzoxazole sulfone and 6.0g of magnesium aluminum silicate are added, after shearing and homogenizing, the materials are poured into a sand mill containing zirconium beads with the volume-mass ratio of 1:1 with a suspending agent, 1.2g of organic silicon defoamer is added, sand milling is started under an ice water bath, after about 4 hours, the particle size is tested by a laser particle size meter, when D90 is about equal to 5-8 mu m, stirring is stopped, and after filtering, the 20% fluorobenzoxazole sulfone suspending agent is obtained.
Example 2: chromatographic conditions for measuring content of crude drug
Chromatographic column: XDB-C18; mobile phase: methanol-water (volume ratio 60:40); flow rate: 1.0mL/min; column temperature: 25 ℃; detection wavelength: 264nm; sample injection amount: 10. Mu.L; retention time of fluorobenzoxazole sulfone: 8min.
Fig. 2-3 show that the content of the raw materials in the preferred formula is measured by a high performance liquid chromatography instrument, and the result shows that decomposed substances appear at about 18.746 peak time after heat storage, and the decomposition rate is more than 70% calculated by an internal standard method. FIG. 4 is a liquid chromatogram of 20% fluorobenzoxazole sulfone suspension with a particle size D90 of 6.22 μm after milling. The decomposition rate is less than 10% by calculation of an internal standard method.
Example 3: main performance test of fluorobenzoxazole sulfone aqueous suspension
According to national or industry standards of related pesticides in China (GB/T14825-2006 pesticide suspension rate measuring method, GB/T19136-2003 pesticide heat storage stability measuring method, GB/T19137-2003 pesticide low temperature stability measuring method, HG/T2467.5-2003 pesticide suspending agent product standard writing specification), main technical indexes of the fluorobenzoxazole sulfone suspending agent are measured.
As shown in Table 6 and FIGS. 2-4, when the particle size of the 20% fluorobenzoxazole sulfone aqueous suspension prepared by using the above auxiliary agent is more than 10 μm, the decomposition rate of the original medicine is larger and is more than 20% after thermal storage (54 ℃ + -2). When the particle size of the suspending agent raw material is 5-8 mu m, the decomposition rate is about 5-10%, and the stability requirement is met. This shows that under the formulation, the formulation and the particle size have important influence on the chemical stability of the original drug of the fluorobenzoxazole sulfone water suspending agent, and the smaller the particle size is, the better the chemical stability of the original drug is.
The main properties of the suspension were tested according to the national standard requirements for pesticide suspensions (GB/T19136-2003), and are shown in Table 8. The result shows that under the formula, the fluorobenzoxazole sulfone water suspending agent is in a milky uniform dispersion system, the dispersibility and the suspension rate are good, and the decomposition rate of the original medicine after heat storage is lower than 10%.
Example 4: pesticide efficacy in vitro test
The method adopts a turbidity method to test the antibacterial EC of 20% of compounds such as fluorobenzoxazole sulfone suspending agent and the like on bacterial blight bacteria (Xoo), bacterial streak bacteria (Xoc) of rice, citrus canker bacteria (Xac), tobacco bacterial wilt bacteria, peach tree perforin bacteria and melon fine angle bacteria of rice 50 Value test:
1. test materials: gun head (5 mL,1mL, 200. Mu.L), 15mL centrifuge tube, secondary water, 2mL EP tube, NB medium all required sterilization.
2. NB medium: beef peptone 3g, peptone 5g, yeast powder 1g, glucose 10g, and secondary water 1L. Subpackaging into test tubes (4 mL/branch), pH=7.0-7.2
3. The operation steps are as follows:
(1) An amount of the compound to be tested was weighed and then dissolved with a corresponding volume (200 μl) of DMSO. A 5% solution system was prepared and diluted to the desired concentration in proportion and the volume was fixed to 4mL with 0.1% tween solution.
(2) 1mL of the mixed solution of the medicinal liquid and warm water was sucked up by a pipette, and the mixed solution was added to a test tube containing 4mL of the culture solution.
(3) 200. Mu.L of the mixed solution (culture medium) was aspirated with a pipette, and the OD was measured with a 96-well plate and recorded.
(4) 50 mu L of bacterial solutions of bacterial leaf blight bacteria (Xoo), bacterial leaf spot bacteria (Xoc) of rice, canker bacteria (Xac), peach tree perforation bacteria, melon fine angle disease and tobacco bacterial wilt bacteria are respectively added into each test tube.
(5) Put into a shaker set at 28℃and 180rpm.
(6) After 24h-36h (OD of CK 0.6-0.8), the OD was measured and recorded, and then the inhibition was calculated.
Corrected OD = bacteria-containing medium OD-sterile medium OD
Inhibition = (corrected control medium broth OD value-corrected bacteria-containing medium OD value)/corrected control medium broth OD value ×100
4. Activity data:
in vitro bacteriostasis bioassay: the principle of the experiment is that compound solutions with different concentrations are prepared and act on bacteria on a culture medium, and the influence of the compounds with different concentrations on the growth and propagation process of the bacteria is observed, so that the minimum inhibitory concentration of one compound can be determined, and the data obtained by the bacteriostasis experiment are the most basic data for evaluating the bacteriostasis performance of the compound.
TABLE 8 EC of 20% Fluobenzole sulfone suspension and other compounds against plant bacterial diseases 50
Table 9 EC of 20% Fluobenzole sulfone suspension and other compounds against plant bacterial diseases 50
As can be seen from tables 8 and 9, the 20% fluorobenzoxazole sulfone suspending agent has an EC against bacterial leaf blight of rice, bacterial leaf spot of rice, citrus canker, tobacco bacterial wilt, peach perforation germ and melon leptosphaeria 50 The values of 0.72 mug/mL, 5.25 mug/mL, 0.93 mug/mL, 15.38 mug/mL, 20.33 mug/mL and 39.78 mug/mL are all superior to the control drug of the thidiazuron copper, the metconazole and the 98.6 percent fluorobenzoxazole sulfone original drug. The 20% fluorobenzoxazole sulfone suspending agent has high-efficiency and broad-spectrum antibacterial activity on plant bacterial diseases.
Example 5: living potted plant test for pesticide effect
The living body pot protection and treatment effect test of the 20% fluorobenzoxazole sulfone suspending agent of the application on rice bacterial leaf blight at the concentration of 200 mug/mL is tested by adopting a leaf-cutting method.
Therapeutic activity:
the scissors dipped with bacterial liquid of rice bacterial leaf blight are used for cutting off 1/3cm part of the leaf tip of the rice leaf, after 24 hours, the 20% fluorobenzoxazole sulfone suspending agent, 98.5% fluorobenzoxazole sulfone technical product, thiabendazole serving as a control medicament and leaf-dried azole are selected, DMSO is respectively added for dissolution, then 0.1% Tween-80 solution is used for preparing the medicament with the concentration of 200 mug/mL, and the medicament is uniformly sprayed on the rice leaf until the liquid drops, and meanwhile, clear water contrast without the medicament is arranged. 10-15 leaves are treated for each rice plant. The disease spot length of the rice leaves is measured after 14 days of application, and the control effect is calculated according to the disease spot length.
Protective activity:
the 20% fluorobenzoxazole sulfone suspending agent, 98.5% fluorobenzoxazole sulfone original drug, control drug thiabendazole and leaf-dried azole are selected, 200 mu L of DMSO is added for dissolution, 0.1% Tween-80 solution is used for preparing the drug with the concentration of 200 mu g/mL, the drug is uniformly sprayed on rice leaves until the drug drops, after 24 hours, scissors containing rice bacterial blight bacteria are used for leaf-cutting inoculation, bacterial solution is at the position of 1/3 of the leaf tips of the rice leaves, and clear water control without the drug is arranged. 10-15 leaves per treatment, 3 replicates. The disease spot length of the rice leaves is measured after 14 days of application, and the control effect is calculated according to the disease spot length.
Table 10 Living potted plant test of 20% Fluobenzole sulfone suspension agent for bacterial leaf blight of rice
As can be seen from Table 10, FIG. 5 and FIG. 6, the 20% fluorobenzoxazole sulfone suspending agent has a good treatment effect on rice bacterial blight at a concentration of 200 mug/mL, and the control effect is 49.5%, which is superior to that of the control drug, namely, the leaf-blight (25.5%), the thiabendazole (37.5%) and the 98.6% fluorobenzoxazole sulfone raw drug (43.4%). Meanwhile, the compound has better protection effect, the prevention effect is 61.1 percent, and the compound is better than that of the control drug of the metconazole (37.2 percent), the thiabendazole (44.5 percent) and the fluorobenzoxazole sulfone raw drug (57.5 percent).
Example 6: test for controlling efficacy in field
The team has carried out field efficacy control experiments in Guangdong, guangxi, hunan, jiangxi and the like, when the dosage of the active ingredients of the 20% fluorobenzoxazole sulfone suspending agent is 120-150 g/hectare, the quick acting performance of the control effect is about 80%, the duration of the control effect is as high as 85%, and the control effect is equivalent to that of the control agent, namely the wettable powder of the biotin and the wettable powder of the metconazole, but the mu dosage is reduced by 60% compared with the traditional bactericides, which indicates that the 20% fluorobenzoxazole sulfone suspending agent is a high-efficiency bactericide.
In a field efficacy control experiment for controlling bacterial diseases of rice bacterial leaf blight, when the dosage of the active ingredients of 20% of the fluorobenzoxazole sulfone suspending agent is 120-150 g/hectare, the dosage per mu is reduced by 50% compared with that of the traditional bactericides, and the control effect is slightly higher than that of the contrast agent 300 g/hectare wettable powder.
The field pesticide effect control experiment for controlling the bacterial angular leaf spot of cotton shows that the average control effect of 50 g/hectare treatment of 20% of the fluorobenzoxazole sulfone suspending agent is 20% higher than that of 300 g/hectare of the agricultural streptomycin wettable powder of 72% of the control agent, and the mu consumption is reduced by 80%.
According to the field efficacy control test for controlling citrus canker, the 20% fluorobenzoxazole sulfone suspending agent has good control effect on citrus canker, and can kill 300 and thiabendazole better than a commercial control agent. In addition, 20% of the fluorobenzoxazole sulfone suspending agent has no phytotoxicity to rice, cotton and citrus and has no influence on other non-target organisms.
Example 7: toxicity test
The application entrusts the toxicity detection center of Guiyang medical college to carry out an acute toxicity experiment of 20% fluorobenzoxazole sulfone suspending agent, and the experimental result shows that the 20% fluorobenzoxazole sulfone suspending agent has low toxicity to non-target organisms.
Toxicology testing of 20% fluorobenzoxazole sulfone suspension:
(one) acute toxicity test of rats
Table 11 acute toxicity test of 20% fluorobenzoxazole sulfone suspension on rats
Acute skin irritation test of white rabbits with big ears
Under the experimental conditions, the average skin irritation score of the animals is 0, and the 20% fluorobenzoxazole sulfone suspending agent has no irritation to the skin of rabbits.
(III) guinea pig skin allergy (sensitization) test
Under the experimental condition, the sensitization rate is 0 percent, and the 20 percent fluorobenzoxazole sulfone suspending agent belongs to a weakly sensitized pesticide.
Environmental toxicity test of 20% Fluobenzole sulfone suspension
Table 12 toxicity test of 20% fluorobenzoxazole sulfone suspension to environmental organisms
The test proves that: 20% of the fluorobenzoxazole sulfone suspending agent has low toxicity to fish, bees and birds.
To sum up: 20% aqueous suspension of fluorobenzoxazole sulfone is a highly effective, low toxicity and broad spectrum bactericide.
Claims (10)
1. A 20% aqueous suspension of fluorobenzoxazole sulfone comprising: 20wt% of fluorobenzoxazole sulfone; 3-12 wt% of surfactant; 0.5 to 2.5 weight percent of thickener; 2-6wt% of antifreezing agent; 0.3 to 0.5 weight percent of organic silicon defoamer; the balance of deionized water; preferably, the raw materials are wet sanded to obtain 20% fluorobenzoxazole sulfone suspending agent.
2. The 20% aqueous suspension of fluorobenzoxazole sulfone according to claim 1, characterized in that: the suspending agent has a suspended particle size of 5-8 μm.
3. The 20% aqueous suspension of fluorobenzoxazole sulfone according to claim 1, characterized in that: the surfactant is selected from ionic or nonionic dispersing agents or wetting agents; preferably, the weight percentage of dispersant or wetting agent is 7.5%.
4. A 20% aqueous suspension of fluorobenzoxazole sulfone according to claim 3, characterized in that: the dispersing agent and the wetting agent consist of a macromolecular amphiphilic anionic non-ionic surfactant compound SC29, sodium dibenzosulfonate HAS040, naphthalene sulfonate sodium salt formaldehyde condensate NNO and sodium paratoluenesulfonate according to the weight ratio of 2:2:2:1.5.
5. The 20% aqueous suspension of fluorobenzoxazole sulfone according to claim 1, characterized in that: the thickener is selected from one or two of magnesium aluminum silicate SF-40 or xanthan gum.
6. The 20% aqueous suspension of fluorobenzoxazole sulfone according to claim 1, characterized in that: the antifreeze is selected from sodium chloride.
7. The 20% aqueous suspension of fluorobenzoxazole sulfone according to claim 1, characterized in that: the silicone defoamer is selected from polydimethyl siloxane.
8. The method for preparing 20% fluorobenzoxazole sulfone aqueous suspension according to claim 1, characterized by comprising the steps of: and taking the surfactant, the antifreezing agent and the water according to the weight percentage, stirring and dissolving, adding the fluorobenzoxazole sulfone and the thickening agent according to the weight percentage, uniformly mixing under the action of a shearing machine, then pumping the mixed slurry into a grinding machine for grinding, adding the organic silicon defoaming agent according to the weight percentage, carrying out particle size test every 1h, stopping stirring after D90 is equal to 5-8 mu m, and filtering to obtain the 20% fluorobenzoxazole sulfone water suspending agent.
9. A method for controlling agricultural plant diseases and insect pests, which is characterized by comprising the following steps: allowing the aqueous suspension according to any one of claims 1 to 7 to act on a pest or its living environment, wherein the pest is rice bacterial leaf blight, rice bacterial leaf streak, citrus canker, tomato bacterial wilt, peach perforation and melon fine angle.
10. A method for protecting plants from agricultural pests comprising the step of contacting a pest with the aqueous suspension of any one of claims 1-7, said pest being rice bacterial leaf blight, bacterial leaf streaks of rice, citrus canker, tomato bacterial wilt, peach perforation and melon fine angle.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310777028.5A CN116831132A (en) | 2023-06-28 | 2023-06-28 | 20% fluorobenzoxazole sulfone water suspension and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310777028.5A CN116831132A (en) | 2023-06-28 | 2023-06-28 | 20% fluorobenzoxazole sulfone water suspension and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116831132A true CN116831132A (en) | 2023-10-03 |
Family
ID=88159286
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202310777028.5A Pending CN116831132A (en) | 2023-06-28 | 2023-06-28 | 20% fluorobenzoxazole sulfone water suspension and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN116831132A (en) |
-
2023
- 2023-06-28 CN CN202310777028.5A patent/CN116831132A/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN108902158A (en) | A kind of suspending agent containing second azoles mite cyanide composition and its application | |
| WO2013081409A1 (en) | Stable aqueous suspension herbicide composition containing glyphosate | |
| CN109418268B (en) | Bactericidal preparation and application thereof | |
| CN106342853B (en) | Plant growth regulator composition with synergistic effect | |
| EA004251B1 (en) | Ectoparasiticidal aqueous suspension formulations of spinosyns | |
| CN106719622B (en) | Pesticide synergistic decrement agent | |
| AU2021100104A4 (en) | Microcapsule suspension of pesticide and preparation method and use thereof | |
| CN109938045A (en) | Composition pesticide containing toVerticilliumdahliaActivitie Activitie S of Relative activator protein and Physcion | |
| CN109757505A (en) | A kind of plant growth regulator composition | |
| CN106259366B (en) | A kind of microbicide compositions | |
| CN116831132A (en) | 20% fluorobenzoxazole sulfone water suspension and preparation method thereof | |
| JPH10500676A (en) | Novel pestiside composition of "oil-in-water emulsion" | |
| CN111084191B (en) | Clothianidin and efficient cyfluthrin suspending agent and preparation method thereof | |
| CN114514936A (en) | Application of thiazole thione in preparing bird repellent | |
| CN104542611A (en) | Bactericidal composition containing mandipropamid | |
| CN104488903B (en) | A kind of containing methylsulfonyl bacterium azoles with the complex composition of the gloomy copper of thiophene | |
| CN107347903A (en) | A kind of composition pesticide containing cycolxylidin and matrine | |
| CN116725019A (en) | Methanesulfonyl bacteria azole suspending agent and preparation method thereof | |
| CN106665614A (en) | Weeding composition containing penoxsulam, bispyribac-sodium and mefenacet | |
| CN111919840A (en) | Binary compound water suspending agent containing chlorfenapyr and food hydrazine inhibitor and preparation method thereof | |
| CN117281117A (en) | Pleuromutilin suspending agent and preparation method thereof | |
| CN107232217B (en) | Bactericide composition and application thereof | |
| CN102484992A (en) | Synergetic pesticide composition of nimbin and tea saponin | |
| CN105394039A (en) | Bactericidal composition containing oxine-copper and ethylicin | |
| CN106259384B (en) | A kind of microbicide compositions |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |