CN101157690B - 1-thia-2- hydrocarbon imino-3,4-diaza-9- oxa (aza )-10-oxo spiro [4.15]-3- eicosanic, preparation method and usage as fungicide - Google Patents

1-thia-2- hydrocarbon imino-3,4-diaza-9- oxa (aza )-10-oxo spiro [4.15]-3- eicosanic, preparation method and usage as fungicide Download PDF

Info

Publication number
CN101157690B
CN101157690B CN2006101404169A CN200610140416A CN101157690B CN 101157690 B CN101157690 B CN 101157690B CN 2006101404169 A CN2006101404169 A CN 2006101404169A CN 200610140416 A CN200610140416 A CN 200610140416A CN 101157690 B CN101157690 B CN 101157690B
Authority
CN
China
Prior art keywords
cauwl
general formula
compounds
oxo
spiro
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.)
Expired - Fee Related
Application number
CN2006101404169A
Other languages
Chinese (zh)
Other versions
CN101157690A (en
Inventor
王道全
李建军
梁晓梅
金淑惠
袁德凯
陈馥衡
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
China Agricultural University
Original Assignee
China Agricultural University
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by China Agricultural University filed Critical China Agricultural University
Priority to CN2006101404169A priority Critical patent/CN101157690B/en
Publication of CN101157690A publication Critical patent/CN101157690A/en
Application granted granted Critical
Publication of CN101157690B publication Critical patent/CN101157690B/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Landscapes

  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

The invention relates to a series of compounds of 1-thia-2-hydrocarbon imino-3, 4-diaza-9-oxo (aza)-10-oxo spiro (4.15)-3-eicosenyl with the general formula of CAUWL-2006-Lj and with a novel chemical structure, a synthesis method and the preparations as the agricultural fungicides. The invention takes 12-oxo-1, 15-pentadecalactone (lactam) as the raw materials, and the series of compounds with the general formula of CAUWL-2006-Lj can be prepared by condensation with the substituted thiosemicarbazide (1) in the appropriate solvent and the cyclization. In the formula, X is O or NH, R is the phenyl with 0 to 2 substituents, and the substituents are halogen, methyl and methoxy. The compounds with the general formula of CAUWL-2006-Lj are dissolved in the solvent, the surfactant is added, such as Nongru 0203B, 0208, GFC, OP-10, Tween-60 and so on, and the milk oil or the wettable powder can be prepared by even mixing by proportion. The compounds with the general formula of CAUWL-2006-Lj andthe preparations can inhibit the growth of seedbed cataplexy pythium aphanidermatum, asparagus stem phomopsis, piricularin pyricularia oryzae, seedbed rhizoctonia solani, sclerotinia sclerotiorum andcucumber botrytis cinerea.

Description

1-thia-2-hydrocarbon imino-3,4-diaza-9-oxygen (nitrogen) is assorted-10-oxo spiral shell [4.15]-3-icosa alkene, its preparation method and as the purposes of sterilant
Technical field
Compound that the present invention relates to and preparation thereof belong to agrochemical field as disinfectant use in agriculture.
Summary of the invention
The general formula that the present invention relates to the chemical structure novelty is 1-thia-2-hydrocarbon imino-3 of CAUWL-2006-Lj, and 4-diaza-9-oxygen (nitrogen) is mixed-10-oxo spiral shell [4.15]-3-icosa alkene series compound, and its synthetic method and preparation are as disinfectant use in agriculture.
X is O or NH in the formula, and R is for having 0～2 substituent phenyl, and substituting group is a halogen, methyl, methoxyl group.
Synthetic route:
Figure GA20185187200610140416901D00012
The implication of X and R is the same in the formula.Promptly with 12-oxo-1,15-muscolactone (lactan) is a raw material, in appropriate solvent through with the condensation of substituted-amino thiocarbamide after again cyclization promptly make the series compound that general formula is CAUWL-2006-Lj.The solvent that is fit to is CH 2Cl 2, ClCH 2CH 2Cl, CH 3CN.
With general formula is that the compound of CAUWL-2006-Lj is dissolved in the solvent, adds tensio-active agent, as the newborn 0203B of farming, and 0208, GFC, OP-10, Tween-60s etc. mix by a certain percentage and are mixed with missible oil or wettable powder.
To be the compound of CAUWL-2006-Lj and preparation thereof have the growth of inhibition effect to damping off pythium spp, the withered Phomopsis of asparagus stem, rice blast Magnaporthe grisea, seedbed dry thread Pyrenomycetes, rape sclerotium sclerotinite, cucumber grey mold Botrytis cinerea of seedbed to general formula.
Embodiment
The present invention can be further described with following example, but the present invention is not limited in these examples.
Synthesizing of example 1 substituted-amino thiocarbamide (1)
Figure GA20185187200610140416901D00021
Reference (Tisler M.Croat Chem Acta, 1956, program 28:147) is carried out.
Example 2 12-oxos-1, and the 15-muscolactone (2, X=O) synthetic
Figure GA20185187200610140416901D00022
The program of reference (Dong Yanhong, Liang Xiaomei, kingly way is complete, chemical reagent, 2003,25:107～108 for Zhang Jianjun, Meng Xiangqing) is carried out.
Example 312-oxo-1, and the 15-pentadelactam (2, X=NH) synthetic
Figure GA20185187200610140416901D00023
The program of reference (Jia Xing HUANG, Xiao MeiLIANG, Dao Quan WANG, Chin.Chem.Lett.2004,15:169～170) is carried out.
Example 4N-(alkyl)-N '-[5-oxygen (nitrogen) is assorted-6-oxo ring 16 subunits contract amino] thiocarbamide (3) synthetic
Figure GA20185187200610140416901D00024
N 2Protection down; in the there-necked flask that reflux condensing tube and thermometer are housed, add compound 22.53g (0.01mmol) and substituted-amino thiocarbamide (1) 2.60g (0.011mmol); add methylene dichloride and ethanol 50mL (3: 1); stirring and dissolving post-heating backflow 12h; cooling; the decompression precipitation gets crude product, and ethyl alcohol recrystallization gets pure product.
The synthetic logical method of example 5CAUWL-2006-Lj series compound
Figure GA20185187200610140416901D00025
3.0mmol compound 3 is dissolved in the anhydrous methylene chloride, stirs adding 8gMnO down 2, continue to stir 30min, filter and use washed with dichloromethane, the decompression precipitation gets crude product, and column chromatography obtains pure product.Its physical constant and ultimate analysis data see Table 1, 1HNMR data and ir data see Table 2, 13C NMR data see Table 3.
Method is led in the preparation of example 6.CAUWL-2006-Lj series compound preparation
(1) missible oil: in the 100ml volumetric flask, add Compound C AUWL-2006-Lj 1～10g, emulsifying agent 5～15g, permeate agent 0.1～1g uses solvent such as toluene then, and it is 1～10% missible oil that constant volumes such as dimethylbenzene get content.
(2) wettable powder: get compound WCAUWL-2006-Lj 15～50g, tensio-active agent 10～20g, white carbon black 30～75g pulverizes to such an extent that content is 15～50% wettable powder through mixed.
The fungicidal activity of example 7.CAUWL-2006-Lj series compound is measured
Adopt the growth velocity assay method, the soup that is about to different concns mixes with the substratum of thawing, makes and is with malicious substratum plane, inoculates pathogenic bacteria in the plane, judges the size of medicament virulence with the speed of germ growth velocity.The fungicidal activity of portion C AUWL-2006-Lj compound sees Table 4.
The physical constant of table 1 Compound C AUWL-2006-Lj and ultimate analysis data
Table 2 Compound C AUWL-2006-Lj's 1HNMR data and IR data
Compound 1HNMR，δ IR(v/cm -1)
CAUWL-2006-Lj-01 1.36-1.75(m，19H)，2.30-2.40(m，5H)，4.12-4.17(m，2H)，7.07-7.12(m，2H)， 7.34-7.40(t，1H)，7.66-7.69(d，1H) 1720，1630，1520
CAUWL-2006-Lj-02 1.28-1.78(m，19H)，2.30-2.420(m，5H)，4.09-4.19(m，2H)，7.16-7.21(d，2H)， 7.54-7.59(d，2H) 1720，1630，1520
CAUWL-2006-Lj-03 1.27-1.77(m，19H)，2.25-2.43(m，5H)，4.08-4.21(m，2H)，7.11-7.20(m，2H)， 7.28-7.35(t，1H)，7.47-7.50(d，1H) 1720，1630，1520
CAUWL-2006-Lj-04 1.38-1.76(m，19H)，2.27-2.41(m，5H)，4.09-4.19(m，2H)，7.23-7.28(d，2H)， 7.39-7.44(d，2H) 1720，1630，1520
CAUWL-2006-Lj-05 1.31-1.75(m，19H)，2.29-2.38(m，8H)，4.09-4.19(m，2H)，7.05-7.08(d，1H)， 7.12-7.17(t，1H)，7.20-7.30(m，2H) 1720，1630，1520
CAUWL-2006-Lj-06 1.37-1.76(m，19H)，2.24-2.40(m，11H)，4.12-4.17(m，2H)，6.86(s，1H)， 6.94-6.96(d，1H)，7.14-7.17(d，1H) 1720，1630，1520
CAUWL-2006-Lj-07 1.24-1.69(m，20H)，2.16-2.37(m，5H)，3.18-3.22(m，1H)，3.51-3.55 (m，1H)，5.73-5.75(s，1H)，7.24-7.31(m，3H)，7.42-4.48(t，2H) 1630，1530
CAUWL-2006-Lj-08 1.21-1.70(m，20H)，2.17-2.42(m，5H)，3.16-3.23(m，1H)，3.49-3.58(m，1H)， 6.08(s，1H)，7.07-7.12(m，2H)，7.34-7.40(t，1H)，7.65-7.68(d，1H) 1630，1530
CAUWL-2006-Lj-09 1.22-1.70(m，20H)，2.18-2.37(m，5H)，3.18-3.23(m，1H)，3.50-3.57(m，1H)， 6.13(t，1H)，7.11-7.20(m，2H)，7.30-7.35(t，1H)，7.47-7.50(d，1H) 1630，1530
CAUWL-2006-Lj-10 1.23-1.69(m，20H)，2.18-2.38(m，5H)，3.18-3.22(m，1H)，3.51-3.57(m，1H)， 5.99-6.02(t，1H)，7.23-7.29(d，2H)，7.39-7.44(d，2H) 1630，1520
CAUWL-2006-Lj-11 1.21-1.73(m，20H)，2.14-2.38(m，8H)，3.18-3.23(m，1H)，3.49-3.55(m，1H)， 6.06-6.10(t，1H)，7.04-7.07(d，1H)，7.12-7.17(t，1H)，7.22-7.29(m，2H) 1630，1530
CAUWL-2006-Lj-12 1.21-1.68(m，20H)，2.17-2.38(m，8H)，3.14-3.20(m，1H)，3.50-3.57(m，1H)， 6.06-6.10(t，1H)，7.22-7.29(m，4H) 1630，1530
CAUWL-2006-Lj-13 1.23-1.68(m，20H)，2.14-2.35(m，5H)，3.17-3.21(m，1H)，3.45-3.50(m，1H)， 5.88-5.92(t，1H)，7.30-7.32(dd，1H)，7.48-7.55(m，3H)，7.74-7.77(d，1H)， 7.85-7.88(m，1H)，8.25-8.28(m，1H) 1630，1530
CAUWL-2006-Lj-14 1.21-1.69(m，20H)，2.16-2.38(m，5H)，3.13-3.20(m，1H)，3.52-3.56(m，1H)， 3.85(s，3H)，5.76(s，1H)，6.97-7.02(d，2H)，7.38-7.44(d，2H) 1630，1530
CAUWL-2006-Lj-15 1.24-1.71(m，20H)，2.18-2.38(m，5H)，3.18-3.21(m，1H)，3.50-3.56(m，1H)， 5.82-6.01(t，1H)，7.10-7.17(m，2H)，7.40-7.43(d，1H) 1630，1530
CAUWL-2006-Lj-16 1.22-1.69(m，20H)，2.14-2.39(m，8H)，3.14-3.21(m，1H)，3.46-3.54(m，1H)， 6.30-6.34(t，1H)，7.06-7.10(m，2H)，7.29-7.35(m，1H) 1630，1530
CAUWL-2006-Lj-17 1.21-1.70(m，20H)，2.15-2.42(m，5H)，3.18-3.25(m，1H)，3.48-3.55(m，1H)， 5.89-5.93(m，1H)，7.12-7.16(d，1H)，7.38-7.40(s，1H)，7.50-7.53(d，1H) 1630，1530
[0035] Table 3 Compound C AUWL-2006-Lj's 13C NMR data
Compound 13C NMR，δ
CAUWL-2006-Lj-01 176.23(C＝N)，173.64(C＝O)，148.01，133.45，128.35，127.07，119.01，115.56(Ar-C)，115.47 (spiro-C)，62.96(C15)，38.93，34.63，34.53，27.83，27.48，26.61，25.97，25.20，25.01，23.85，23.31 (C2-C11，C13，C14)
CAUWL-2006-Lj-02 173.82(C＝N)，173.61(C＝O)，147.00，132.46，122.80，120.11(Ar-C)，115.65(spiro-C)，62.94(C15)， 38.96，34.63，34.59，27.84，27.48，26.63，26.52，26.04，25.28，25.01，23.97，23.37(C2-C11，C13，C14)
CAUWL-2006-Lj-03 176.17(C＝N)，173.60(C＝O)，146.50，130.36，127.62，126.86，125.88，119.21(Ar-C)，115.48 (spiro-C)，62.95(C15)，38.94，3462，34.56，27.84，27.48，26.63，26.48，26.00，25.24，25.01，23.86， 23.35(C2-C11，C13，C14)
CAUWL-2006-Lj-04 173.78(C＝N)，173.69(C＝O)，146.48，132.29，129.53，122.60(Ar-C)，115.66(spiro-C)，62.99(C15)， 39.01，34.68，34.65，27.88，27.53，26.66，26.54，26.06，25.28，25.06，24.00，23.39(C2-C11，C13，C14)
CAUWL-2006-Lj-05 173.97(C＝N)，173.71(C＝O)，147.87，130.90，126.67，126.33，117.02(Ar-C)，114.35(spiro-C)，63.06 (C15)，39.10，34.70，27.89，27.54，27.18，26.67，26.53，26.06，25.28，25.07，23.93，23.31，17.85 (C2-C11，C13，C14)
CAUWL-2006-Lj-06 173.62(C＝N)，173.58(C＝O)，147.66，136.31，130.68，127.09，126.93，117.40(Ar-C)，114.14 (spiro-C)，63.01(C15)，39.07，34.68，34.62，27.82，27.48，26.63，26.51，26.02，25.26，25.00，23.90， 23.26，20.98，17.31(C2-C11，C13，C14)
CAUWL-2006-Lj-07 173.6(C＝N)，173.3(C＝O)，148.0，129.4，126.9，121.1(Ar-C)，115.2(spiro-C)，39.5(C15)，38.1，36.9， 34.8，27.9，27.6，27，263，25.8，25.6，24.7，24.6，23.0(C2-C11，C13，C14)
CAUWL-2006-Lj-08 176.5(C＝N)，173.4(C＝O)，147.9，133.4，128.4，127.1，119.0，115.8(Ar-C)，115.5(spiro-C)，39.4(C15 )，38.0，36.8，34.7，27.8，27.5，26.9，26.2，257，25.5，24.6，24.5，23.0(C2-C11，C13，C14)
CAUWL-2006-Lj-09 176.5(C＝N)，173.4(C＝O)，146.4，130.3，127.7，126.9，125.8，119.2(Ar-C)，115.8(spiro-C)，39.3 (C15)，37.9，36.8，34.7，27.8，27.5，26.9，262，25.7，25.5，24.6，24.5，23.0(C2-C11，C13，C14)
CAUWL-2006-Lj-10 173.9(C＝N)，173.4(C＝O)，146.3，132.2，129.5，122.5(Ar-C)，115.8(spiro-C)，39.3(C15)，37.9，36.8， 34.7，27.8，27.5，26.9，26.1，25.6，25.5，24.5，24.4，22.9(C2-C11，C13，C14)
CAUWL-2006-Lj-11 174.2(C＝N)，173.3(C＝O)，147.8，130.8，130.3，126.6，126. 3，116.9(Ar-C)，114.5(spiro-C)，39.4 (C15)，38.0，36.8，34.8，27.8，27.6，26.9，26.2，25.7，25.5，24.6，24.5，22.9，17.8(C2-C11，C13，C14)
CAUWL-2006-Lj-12 173.3(C＝N)，172.5(C＝O)，145.0，137.1，129.9，121.4(Ar-C)，115.1(spiro-C)，39.4(C15)，38.0，36.8， 34.8，27.8，26.9，26.2，25.7，25.6，24.6，24.5，22.9，21.1(C2-C11，C13，C14)
CAUWL-2006-Lj-13 174.4(C＝N)，173.3(C＝O)，145.2，134.1，127.8，127.6，126.9，126.7，1262，125.5，123.4，114.8(Ar-C)， 113.2(spiro-C)，39.4(C15)，38.0，36.8，34.8，27.8，27.6，26.9，26.2，25.7，25.6，24.6，24.5，23.0 (C2-C11，C13，C14)
CAUWL-2006-Lj-14 173.3(C＝N)，170.6(C＝O)，158.9，139.8，124.0，115.3(Ar-C)，114.5(spiro-C)，55.5(O CH3)， 39.5(C15)，38.1，37.0，34.8，27.9，27.6，27.0，26.3，25.8，25.6，24.7，24.6，23.0(C2-C11，C13，C14)
CAUWL-2006-Lj-15 177.2(C＝N)，173.4(C＝O)，147.3，133.2，131.3，126.6，124.0，119.4(Ar-C)，116.6(spiro-C)， 39.3(C15)，37.9，36.8，34.7，27.8，27.5，26.9，26.2，25.7，25.5，24.6，24.5，23.1(C2-C11，C13，C14)
CAUWL-2006-Lj-16 173.4(C＝N)，173.3(C＝O)，147.9，139.2，129.1，127.6，121.6，117.6(Ar-C)，115.0(spiro-C)， 39.3(C15)，37.9，36.7，34.8，27.7，27.5，26.8，26.2，25.6，25.5，24.6，24.5，22.9，21.3(C2-C11，C13，C14)
CAUWL-2006-Lj-17 174.9(C＝N)，173.3(C＝O)，147.5，133.2，131.1，130.2，122.8，120.6(Ar-C)，116.5(spiro-C)， 393(C15)，38.0，36.8，34.7，27.8，27.5.26.9，26.2，25.7，25.5，24.6，24.6，23.1(C2-C11，C13，C14)
[0037] Compound C AUWL-2006-Lj is to the growth inhibition ratio (%) of six kind of plant pathogenic fungies during table 4 50ug/m1
Compound Pythium spp (dampinging off in the seedbed) Phomopsis (the asparagus stem is withered) Magnaporthe grisea (rice blast) Rhizoctonia (seedbed is upright withered) Sclerotinite (rape sclerotium) Botrytis cinerea (cucumber grey mold)
CAUWL-2006-Lj-01 81.6 10.8 51.0 24.6 75.0 75.0
CAUWL-2006-Lj-02 9.3 10.8 87.8 45.7 63.1 55.6
CAUWL-2006-Lj-03 18.1 97.2 51.0 69.5 38.3 66.0
CAUWL-2006-Lj-04 9.3 30.6 69.8 45.7 - 30.6
CAUWL-2006-Lj-05 9.3 69.1 43.8 29.1 87.3 37.3
CAUWL-2006-Lj-06 9.3 10.8 43.8 37.7 - 8.2
CAUWL-2006-Lj-07 45.2 75.0 50.5 64.0 80.0 70.6
CAUWL-2006-Lj-08 29.4 48.3 55.6 52.3 32.6 32.2
CAUWL-2006-Lj-09 36.0 60.9 55.6 41.7 60.7 58.1
CAUWL-2006-Lj-10 29.4 52.7 50.5 54.7 52.9 48.1
CAUWL-2006-Lj-11 42.2 68.4 60.4 54.7 66.1 67.1
CAUWL-2006-Lj-12 29.4 68.4 50.5 47.1 62.6 43.8
CAUWL-2006-Lj-13 7.8 12.1 50.5 64.1 50.8 0
CAUWL-2006-Lj-14 32.8 56.9 60.4 74.1 66.1 48.1
CAUWL-2006-Lj-15 26.0 34.0 80.2 41.7 39.8 22.1
CAUWL-2006-Lj-16 36.0 56.9 50.5 54.7 72.7 43.8
CAUWL-2006-Lj-17 11.6 48.3 93.3 41.7 48.7 27.2

Claims (3)

1. 1-thia-2-hydrocarbon imino-3 that following general formula is CAUWL-2006-Lj, 4-diaza-9-oxygen (nitrogen) is mixed-10-oxo spiral shell [4.15]-3-icosa alkene series compound:
Figure FA20185187200610140416901C00011
X is O or NH in the formula, and R is for having 0～2 substituent phenyl, and substituting group is a halogen, methyl, methoxyl group.
2. the missible oil or the wettable powder that are mixed with of the compound in the claim 1.
3. the compound in the claim 1 is as disinfectant use in agriculture.
CN2006101404169A 2006-10-08 2006-10-08 1-thia-2- hydrocarbon imino-3,4-diaza-9- oxa (aza )-10-oxo spiro [4.15]-3- eicosanic, preparation method and usage as fungicide Expired - Fee Related CN101157690B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN2006101404169A CN101157690B (en) 2006-10-08 2006-10-08 1-thia-2- hydrocarbon imino-3,4-diaza-9- oxa (aza )-10-oxo spiro [4.15]-3- eicosanic, preparation method and usage as fungicide

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN2006101404169A CN101157690B (en) 2006-10-08 2006-10-08 1-thia-2- hydrocarbon imino-3,4-diaza-9- oxa (aza )-10-oxo spiro [4.15]-3- eicosanic, preparation method and usage as fungicide

Publications (2)

Publication Number Publication Date
CN101157690A CN101157690A (en) 2008-04-09
CN101157690B true CN101157690B (en) 2010-08-11

Family

ID=39305938

Family Applications (1)

Application Number Title Priority Date Filing Date
CN2006101404169A Expired - Fee Related CN101157690B (en) 2006-10-08 2006-10-08 1-thia-2- hydrocarbon imino-3,4-diaza-9- oxa (aza )-10-oxo spiro [4.15]-3- eicosanic, preparation method and usage as fungicide

Country Status (1)

Country Link
CN (1) CN101157690B (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101624396B (en) * 2009-06-01 2011-07-20 中国农业大学 Spiro-compound containing thiadiazoline and furanring, preparation method and germicide application thereof
CN102060802B (en) * 2010-12-10 2012-09-05 广西壮族自治区海洋研究所 Nitrogen and sulfur heterocyclic compound, preparation method and application thereof
CN102153602B (en) * 2011-02-24 2013-11-06 中国农业大学 Furanosyl modified 1,3,4-thiadiazole derivative and preparation method thereof as well as application of derivative as bactericide

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1519233A (en) * 2003-09-02 2004-08-11 中国农业大学 12-(imino ether)-1, 15-pentadelactam, as well as preparation method and its application in bactericide

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1519233A (en) * 2003-09-02 2004-08-11 中国农业大学 12-(imino ether)-1, 15-pentadelactam, as well as preparation method and its application in bactericide

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
张建军等.12-(酰氧亚氨基)-1 15-十五内酯的合成及结构表征.高等学校化学学报24 9.2003
张建军等.12-(酰氧亚氨基)-1,15-十五内酯的合成及结构表征.高等学校化学学报24 9.2003,24(9),1604-1609. *
陈莉等.2-(1,11-十一亚甲基)-5-取代亚氨基-Δ3-1,3,4-噻二唑啉的合成及杀菌活性.应用化学19 3.2002,19(3),212-215.
陈莉等.2-(1,11-十一亚甲基)-5-取代亚氨基-Δ3-1,3,4-噻二唑啉的合成及杀菌活性.应用化学19 3.2002,19(3),212-215. *

Also Published As

Publication number Publication date
CN101157690A (en) 2008-04-09

Similar Documents

Publication Publication Date Title
EP3312162B1 (en) 1-(2-(ethylsulfonyl)-phenyl)-4-(phenyl)-1h-pyrazole derivatives and related compounds as pesticides
JP6865873B2 (en) Diarylimidazole compounds and pest control agents
BR112018011691B1 (en) Compound, pest, ectoparasite and endoparasite control agents or an endoparasite expelling agent, and insecticide or acaricide
CN101157690B (en) 1-thia-2- hydrocarbon imino-3,4-diaza-9- oxa (aza )-10-oxo spiro [4.15]-3- eicosanic, preparation method and usage as fungicide
CN103664808B (en) A kind of aryl 3-triazole compounds containing chlorocyclopropane and preparation method thereof and application
RU2670439C2 (en) Substituted pyrazolyl pyrazole derivative and use thereof as herbicide
CN103059006B (en) Chrysin-1,2,3-triazole compound with anti-microbial activity and preparation method thereof
TW201813962A (en) Diaryl-azole compound and formulation for controlling harmful organism
EP3556751B1 (en) Diarylpyrazole compound and pest control agent
US20220369637A1 (en) Pyridinium salt and pest control agent
CN102336744A (en) Substituted triazoline ether ketone class compound and application thereof as bactericide as well as insecticide and acaricide
CN102336742A (en) Substituted triazolinone ether compounds and application thereof
CN102336743A (en) Triazoline ketone ether-substituted compound and application thereof
WO2020241632A1 (en) Pyridinium salt and pest control agent
CN105367548A (en) Cyan dihalogenation pyrazol amide series compound and preparation method and application thereof
CN102276552B (en) 1,3,4-thiadiazoline derivative containing cyclopropanyl, preparation method thereof and application thereof as bactericide
CN103772283A (en) Pyrazole compound containing aromatic ring and dihalide substituent as well as preparation method and use thereof
WO2021049522A1 (en) Onium salt of nitrogen-containing heteroaryl compound and pest control agent
CN102153602A (en) Furanosyl modified 1,3,4-thiadiazole derivative and preparation method thereof as well as application of derivative as bactericide
US20210002263A1 (en) Heteroarylpyrimidine compound and formulation for controlling harmful organisms
Peña et al. A new series of acylhydrazones derived from metribuzin with modulated herbicidal activity
WO2020133092A1 (en) Pyridyloxy-carboxylate derivative and preparation method therefor, herbicidal composition, and use
CN1401648A (en) Heterocycle substd. condensed heterocyclic derivs. with bioactivity
CN101659660B (en) Preparation for biphenyl substituted 1,3,4-thia(oxa)diazole derivatives and use thereof as herbicide
CN105859645A (en) Halogen-substituted triazole compound with benzene rings, method for preparing halogen-substituted triazole compound and application thereof

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant
C17 Cessation of patent right
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20100811

Termination date: 20121008