CN110973149B - Application of sulfur-containing isocyanate compounds in blue-green algae growth inhibition - Google Patents

Application of sulfur-containing isocyanate compounds in blue-green algae growth inhibition Download PDF

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CN110973149B
CN110973149B CN201911265537.XA CN201911265537A CN110973149B CN 110973149 B CN110973149 B CN 110973149B CN 201911265537 A CN201911265537 A CN 201911265537A CN 110973149 B CN110973149 B CN 110973149B
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methylene
chlorine
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CN110973149A (en
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万坚
任彦亮
黄运远
郭邦烨
黄玉华
饶立
胡赛亚
冯玲玲
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Central China Normal University
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • A01N47/46—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=C=S groups

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Abstract

The invention relates to an application of sulfur-containing isocyanate compounds in blue algae growth inhibition. It has the structure shown in general formula I and general formula II, wherein R in general formula I1Represents methyl, phenethyl, phenyl, 4-methylpyridine or 3-methylpyridine; in the general formula II, M represents carbonyl, methylene, methine phenyl, R3Represents hydrogen, chlorine; r4Represents oxygen, hydrogen, fluorine, chlorine; r5Represents oxygen, hydrogen, chlorine, methyl, fluorine, benzene ring, bromine, trifluoromethyl, R4And R5When it is oxygen, R4，R5Cyclizing to form 1, 3-dioxole; r6Represents hydrogen, fluorine, bromine, trifluoromethyl, methyl, chlorine; r7Represents hydrogen, trifluoromethyl, chlorine, bromine. The sulfur-containing isocyanate compound with the structure shown in the general formulas I and II has a good inhibition effect on blue-green algae, and can be used as an effective component of a blue-green algae algicide.

Description

Application of sulfur-containing isocyanate compounds in blue-green algae growth inhibition
Technical Field
The invention relates to an application of sulfur-containing isocyanate compounds in blue algae growth inhibition.
Background
In recent years, the water eutrophication is more and more serious due to the sharp increase of human production and living activities and the generation of a large amount of produced garbage, algae bloom events are continuously and massively developed in various places, the ecological environment is seriously damaged, the water source is polluted, and huge hidden dangers are brought to the human production and living. Therefore, how to effectively and simply treat algal bloom becomes a problem to be solved urgently. The exploration and discovery of pesticide compounds with high activity and low toxicity are the focus of current pesticide research.
Disclosure of Invention
The invention aims to provide application of sulfur isocyanate compounds in blue algae growth inhibition.
The invention provides application of sulfur-containing isocyanate compounds represented by general formulas I and II in blue algae inhibition, which have structures represented by general formulas I or II:
Figure BDA0002312711900000011
in the general formula I, R1Represents methyl, phenethyl, phenyl, 4-methylpyridine or 3-methylpyridine;
Figure BDA0002312711900000012
in the general formula II, M represents carbonyl, methylene, methine phenyl group (
Figure BDA0002312711900000013
),R3Represents hydrogen, chlorine; r4Represents oxygen, hydrogen, fluorine, chlorine; r5Represents oxygen, hydrogen, chlorine, methyl, fluorine, benzene ring, bromine, trifluoromethyl, R4And R5When it is oxygen, R4，R5Cyclizing to form 1, 3-dioxole; r6Represents hydrogen, fluorine, bromine, trifluoromethyl, methyl, chlorine; r7Represents hydrogen, trifluoromethyl, chlorine, bromine.
According to the scheme, when M in the compound of the general formula II is not methylene, R3,R4,R5,R6,R7At least one of which is not hydrogen.
According to the scheme, in the compound of the general formula II:
m represents a carbonyl group, R3,R4,R5,R6,R7Represents hydrogen;
or M represents methylene, R3,R4,R5,R7Represents hydrogen, R6Represents bromine;
or M represents methylene, R4,R5,R6,R7Represents hydrogen, R3Represents chlorine;
or M represents a methinyl group, R3,R4,R5,R6,R7Represents hydrogen;
or M represents methylene, R3,R6,R7Represents hydrogen, R4,R5Ring formation to form 1, 3-dioxole;
or M represents methylene, R3,R4,R5,R6,R7Represents hydrogen, R4,R5Represents chlorine;
or M represents methylene, R3,R4,R6,R7Represents hydrogen, R5Represents chlorine;
or M represents methylene, R3,R4,R6,R7Represents hydrogen, R5Represents a methyl group;
or M represents methylene, R3,R4,R6,R7Represents hydrogen, R5Represents fluorine;
or M represents methylene, R3,R4,R5,R7Represents hydrogen, R6Represents chlorine;
or M represents methylene, R3, R4, R5, R7 represents hydrogen, R6 represents fluoro;
or M represents methylene, R4, R5, R6, R7 represents hydrogen, R3 represents methyl;
or M represents methylene, R3,R4,R6,R7Represents hydrogen, R5Represents a benzene ring;
or M represents methylene, R3,R4,R6Represents hydrogen, R5,R7Represents chlorine;
or M represents methylene, R3,R4,R5,R6Represents hydrogen, R7Represents chlorine;
or M represents methylene, R3,R5,R7Represents hydrogen, R4,R6Represents fluorine;
or M represents methylene, R3,R4,R6,R7Represents hydrogen, R5Represents bromine;
or M represents methylene, R3,R4,R5,R6Represents hydrogen, R7Represents trifluoromethyl;
or M represents methylene, R3,R4,R5,R7Represents hydrogen, R6Represents trifluoromethyl;
or M represents methylene, R3,R4,R6,R7Represents hydrogen, R5Represents trifluoromethyl;
or M represents methylene, R3,R4,R5,R6Represents hydrogen, R7Represents bromine;
or M represents methylene, R3,R4,R5,R7Represents hydrogen, R6Represents a methyl group;
or M represents methylene, R3,R5,R7Represents hydrogen, R4,R6Represents chlorine.
The blue algae algicide takes a sulfur-containing isocyanate compound shown in a general formula I or a general formula II as an effective active component.
The sulfur isocyanates of formula I or formula II are commercially available or can be directly seeded as follows: reacting an amine compound R1NH2Or
Figure BDA0002312711900000031
Dissolving in an anhydrous tetrahydrofuran solvent, adding triethylamine, placing in an ice bath condition, adding carbon disulfide for reaction for 1 hour, adding p-toluenesulfonyl chloride (PTSC) into a flask, removing the ice bath, stopping the reaction after reacting for one hour, adding diluted hydrochloric acid for acidification, extracting for three times by using anhydrous ether, combining organic phases after liquid separation, adding anhydrous sodium sulfate for drying, adding sample silica gel for spin-drying and column-loading after drying, and performing fast column chromatography by using petroleum ether to obtain the compound.
With amine compounds
Figure BDA0002312711900000032
For example, the reaction scheme is:
Figure BDA0002312711900000041
wherein: r1、R3、R4、R5、R6The definition of (b) is the same as that of the sulfur isocyanate compound represented by formula I, II, and TEA is triethylamine.
The invention has the beneficial effects that:
the sulfur-containing isocyanate compound with the structure shown in the general formulas I and II has a good inhibition effect on blue-green algae, and can be used as an effective component of a blue-green algae algicide.
Detailed Description
The preparation of the compound of formula II of the present invention is illustrated in more detail by example 1
Example 1
Compound SF2
Preparation of benzyl isothiocyanates
Figure BDA0002312711900000042
Dissolving 8mmol benzylamine in 15ml anhydrous tetrahydrofuran solvent, adding 5ml (36mmol) triethylamine, placing in ice bath condition, adding 2ml (33mmol) carbon disulfide for reaction for 1 hour, adding 2g (10.5mmol) p-toluenesulfonyl chloride (PTSC) in a flask, removing ice bath, stopping reaction after reaction for one hour, adding 20ml 0.5mol/L diluted hydrochloric acid for acidification, extracting with 60ml anhydrous ether for three times, combining organic phases after liquid separation, adding anhydrous sodium sulfate for drying, adding a sample silica gel for spin drying, and performing fast column chromatography by using petroleum ether (developing agent: petroleum ether Rf value 0.4-0.6. pyridine ring type thioisocyanate, developing agent: ethyl acetate; petroleum ether Rf value 1; 5, Rf value 0.4-0.5) to obtain transparent oily liquid (yield is 75-80%).
The molecular formula is as follows: c8H7NS
1H NMR(600MHz,Chloroform-d)δ7.37(t,J＝7.1Hz,2H),7.33(d,J＝7.0Hz,1H),7.29(d,J＝7.0Hz,2H),4.67(s,2H).13C NMR(600MHz,Chloroform-d)δ132.09,128.96,128.37,126.84,48.66.
Compounds SF11-SF15, SF17-SF18 and SF22-SF30 are prepared analogously to Compound II
Compound SF10
3, 4-dichlorobenzyl isothiocyanate
Figure BDA0002312711900000051
The molecular formula is as follows: c8H5Cl2NS1H NMR(400MHz,Chloroform-d)δ7.45(d,J＝8.3Hz,1H),7.40(s,1H),7.16(d,J＝8.3Hz,1H),4.69(s,2H).13C NMR(101MHz,Chloroform-d)δ134.37,133.06,132.54,130.91,128.80,126.09,47.61.MS(m/z):calculated for C7H5Cl2NCS+[M]+:218.10,found 216.95.
Compound SF11
4-chlorobenzyl thiocyanate
Figure BDA0002312711900000052
The molecular formula is as follows: c8H6ClNS
1H NMR(400MHz,Chloroform-d)δ7.33(d,J＝8.2Hz,2H),7.22(d,J＝8.2Hz,2H),4.65(s,2H).13C NMR(400MHz,Chloroform-d)δ134.25,132.83,129.15,128.30,48.14.MS(m/z):calculated for C8H5ClNS+[M]+:183.65,found 183.00.
Compound SF12
4-methyl thiocyanate
Figure BDA0002312711900000061
The molecular formula is as follows: c9H9NS
1H NMR(600MHz,DMSO-d6)δ7.27(d,J＝6.9Hz,2H),7.22(d,J＝7.5Hz,2H),4.87(s,2H),2.31(s,3H).13C NMR(600MHz,DMSO-d6)δ137.75,131.96,129.68,127.30,48.03,20.94.MS(m/z):calculated for C9H9NS+[M]+:163.24,found 163.05.
Compound SF13
4-Fluorobenzylthiocyanates
Figure BDA0002312711900000062
The molecular formula is as follows: c8H6FNS
1H NMR(600MHz,DMSO-d6)δ7.44(dd,J＝8.5,5.6Hz,2H),7.25(t,J＝8.9Hz,2H),4.93(s,2H).13C NMR(600MHz,DMSO-d6)δ144.62,138.95,128.74,125.88,21.17.MS(m/z):calculated for C8H6NCS+[M]+:167.20,found 167.00.
Compound SF14
3-chlorobenzyl thiocyanate
Figure BDA0002312711900000071
The molecular formula is as follows: c8H6ClNS
1H NMR(600MHz,DMSO-d6)δ7.46(s,1H),7.43(d,J＝7.6Hz,1H),7.40(d,J＝8.1Hz,1H),7.35(d,J＝7.3Hz,1H),4.96(s,2H).13C NMR(600MHz,DMSO-d6)δ137.26,133.68,130.82,128.32,127.29,125.95,47.64.MS(m/z):calculated for C8H5ClNS+[M]+:183.65,found 183.00.
Compound SF15
3-Fluorobenzylthiocyanates
Figure BDA0002312711900000072
The molecular formula is as follows: c8H6FNS
1H NMR(600MHz,Chloroform-d)δ7.61(s,1H),7.56(s,1H),7.53(d,J＝3.6Hz,2H),4.80(s,2H).C NMR(600MHz,Chloroform-d)δ135.43,131.56,130.32,129.75,125.39,123.80.MS(m/z):calculated for C8H6FNS+[M]+:167.20,found 167.00.
Compound SF17
Biphenyl-4-methylthioisocyanate
Figure BDA0002312711900000073
Molecular formula C14H11NS
1H NMR(600MHz,DMSO-d6)δ7.39(dd,J＝7.9,3.3Hz,4H),7.16(t,J＝7.3Hz,1H),7.03(t,J＝8.3Hz,4H),4.91(d,J＝2.2Hz,2H).13C NMR(600MHz,DMSO-d6)δ156.76,156.42,130.23,129.71,129.34,123.84,118.94,47.58.MS(m/z):calculated for C14H11NS+[M]+:225.31,found 225.05.
Compound SF18
2, 4-dichlorobenzyl isothiocyanate
Figure BDA0002312711900000081
The molecular formula is as follows: c8H5Cl2NS
1H NMR(600MHz,Chloroform-d)δ7.43–7.37(m,2H),7.31(d,J＝8.2Hz,1H),4.79(s,2H).13C NMR(600MHz,Chloroform-d)δ135.00,133.30,130.71,129.59,129.52,127.68,46.31.MS(m/z):calculated for C8H5Cl2NS+[M]+:218.10,found 216.95.
Compound SF22
4-phenoxybenzylthioisocyanates
Figure BDA0002312711900000082
The molecular formula is as follows: c14H11NOS
1H NMR(600MHz,DMSO-d6)δ7.72(d,J＝8.0Hz,2H),7.68(d,J＝7.7Hz,2H),7.48(t,J＝7.3Hz,4H),7.39(t,J＝7.3Hz,1H),4.99(s,2H).13C NMR(600MHz,DMSO-d6)δ140.34,139.78,134.18,129.28,128.13,127.44,127.00.MS(m/z):calculated for C14H11NOS+[M]+:241.31,found 241.00.
Compound SF23
3, 5-difluorobenzyl isothiocyanate
The molecular formula is as follows: c8H5F2NS
Figure BDA0002312711900000091
1H NMR(600MHz,Chloroform-d)δ6.86(d,J＝5.9Hz,2H),6.79(t,J＝8.7Hz,1H),4.73(s,2H).13C NMR(600MHz,Chloroform-d)δ164.18,162.52,138.13,109.99,103.97,48.01.MS(m/z):calculated for C8H5F2NS+[M]+:185.19,found 185.01.
Compound SF24
4-bromobenzyl isothiocyanate
Figure BDA0002312711900000092
The molecular formula is as follows: c8H6BrNS
1H NMR(600MHz,Chloroform-d)δ7.50(d,J＝8.2Hz,2H),7.18(d,J＝8.1Hz,2H),4.66(s,2H).13C NMR(600MHz,Chloroform-dδ132.19,128.65,122.46,48.25.MS(m/z):calculated for C8H6BrNS+[M]+:228.11,found 228.95.
Compound SF25
2-trifluoromethylbenzyl isothiocyanate
Figure BDA0002312711900000101
The molecular formula is as follows: c9H6F3NS
1H NMR(600MHz,Chloroform-d)δ7.86–7.58(m,3H),7.47(s,1H),4.95(s,2H).13C NMR(600MHz,Chloroform-d)δ126.82,123.15,122.70,120.46,119.03,39.90.19F NMR(400MHz,Chloroform-d)δ-60.32.MS(m/z):calculated for C9H6F3NS+[M]+:217.21,found 217.00.
Compound SF26
3-trifluoromethylbenzyl isothiocyanate
Figure BDA0002312711900000102
The molecular formula is as follows: c9H6F3NS
1H NMR(600MHz,Chloroform-d)δ7.61(s,1H),7.57(s,1H),7.54(s,2H),4.80(s,2H).13C NMR(600MHz,Chloroform-d)δ130.34,129.79，125.46,123.85,48.44.19F NMR(400MHz,Chloroform-d)δ-62.74.MS(m/z):calculated for C9H6F3NS+[M]+:217.21,found 217.00.
Compound SF27
4-trifluoromethylbenzyl isothiocyanate
Figure BDA0002312711900000103
The molecular formula is as follows: c9H6F3NS
1H NMR(600MHz,Chloroform-d)δ7.61(dd,J＝126.6,29.6Hz,4H),4.84(s,2H).13C NMR(600MHz,Chloroform-d)δ138.42,133.72,130.84,127.24,126.12,48.36.19F NMR(400MHz,Chloroform-d)δ-62.64.MS(m/z):calculated for C9H6F3NS+[M]+:217.21,found 217.00.
Compound SF28
2-bromobenzyl isothiocyanate
Figure BDA0002312711900000111
The molecular formula is as follows: c8H6BrNS
1H NMR(600MHz,Chloroform-d)δ7.57(d,J＝7.8Hz,1H),7.44(d,J＝7.3Hz,1H),7.36(t,J＝7.4Hz,1H),7.22(t,J＝7.5Hz,1H),4.80(s,2H).13C NMR(600MHz,Chloroform-d)δ133.72,133.12,130.10,128.89,128.11,122.52,49.29.MS(m/z):calculated for C8H6BrNS+[M]+:228.11,found 226.90.
Compound SF29
3-methylbenzyl isothiocyanate
Figure BDA0002312711900000112
The molecular formula is as follows: c9H9NS
1H NMR(600MHz,Chloroform-d)δ7.27–7.21(m,1H),7.14(d,J＝7.4Hz,1H),7.09(d,J＝10.0Hz,2H),4.64(s,2H),2.35(s,3H).13C NMR(600MHz,Chloroform-d)δ129.19,128.94,127.64,123.99,48.70,21.52.MS(m/z):calculated for C9H9NS+[M]+:163.24,found 163.05.
Compound SF30
3, 5-dichlorobenzyl isothiocyanate
Figure BDA0002312711900000121
MoleculeFormula (II): c8H5Cl2NS
1H NMR(600MHz,Chloroform-d)δ7.33(s,1H),7.25–7.16(m,2H),4.71(s,2H).13C NMR(600MHz,Chloroform-d)δ137.57,135.73,128.74,125.43,47.81.MS(m/z):calculated for C7H5Cl2NCS+[M]+:218.10,found 216.95。
Example 2
Synechocystis PCC6803 is one of the most important model algae of cyanobacteria. Synechocystis PCC6803 algal body growth inhibition experiments were performed on the above compounds.
Separately inoculating Synechocystis PCC6803 with the same volume into BG-11(+ N) liquid culture medium containing different sulfur isocyanate compounds, and culturing in a climatic chamber. The whole culture temperature is controlled at about 28 ℃, the humidity is 60%, the light intensity is set to be 60001x, the culture is dark for 12 hours, the culture is illuminated for 12 hours, and the model is vibrated.
The specific operation details are as follows:
1. a batch of Synechocystis PCC6803 was cultured in advance, and after 4-7 days of log phase growth, its OD680 was determined.
2. Diluting the logarithmic phase algae solution with BG-11(+ N) culture medium to obtain inoculated algae solution, and controlling the cell concentration of algae to about 1 × 106Per mL
3. The corresponding compounds were weighed in advance, dissolved in DMSO, and compounds at different concentrations were prepared. 200. mu.L of diluted inoculum was added to each well of a 96-well plate, followed by 1. mu.L of a compound at a given concentration. Making 5 groups of compounds with each concentration in parallel, and simultaneously setting a control group without the compounds and a compound Beijing control;
4. and (5) measuring the OD680 value by using an enzyme-labeling instrument after culturing for 7 days in the artificial climate box, and calculating the growth rate of the blue algae inhibited by the compounds with different concentrations.
The inhibition ratio formula calculates:
growth inhibition rate: [ blank OD680- (drug group 680-Compound background OD680) ]. times.100/blank OD 680;
5. the concentration of the compound is plotted on the abscissa and the growth inhibition is plotted on the ordinate, and fitted to the formula logistic in Oringin to obtain the compound ec50.
6. Table one compound of formula I and formula II inhibits the growth of blue algae by EC50 value.
Figure BDA0002312711900000131
Figure BDA0002312711900000141
Figure BDA0002312711900000151

Claims (3)

1. The application of the sulfur-containing isocyanate compound shown in the general formula I or the general formula II or the general formula III in blue algae inhibition has the structure shown in the general formula I or the general formula II or the general formula III:
Figure FDA0003194221460000011
in the general formula I, R1Represents methyl, phenethyl, benzyl, phenyl, 4-methylpyridine or 3-methylpyridine;
Figure FDA0003194221460000012
in the general formula II, M represents carbonyl, methylene, methine phenyl, R3Represents hydrogen, chlorine; r4Represents oxygen, hydrogen, fluorine, chlorine; r5Represents oxygen, hydrogen, chlorine, methyl, fluorine, benzene ring, bromine, trifluoromethyl, R4And R5When it is oxygen, R4，R5Cyclizing to form 1, 3-dioxole; r6Represents hydrogen, fluorine, bromine, trifluoromethyl, methyl, chlorine; r7Represents hydrogen, trifluoromethyl, chlorine, bromine;
Figure FDA0003194221460000013
2. use according to claim 1, characterized in that: in the compounds of the general formula II:
m represents a carbonyl group, R3,R4,R5,R6,R7Represents hydrogen;
or M represents methylene, R3,R4,R5,R7Represents hydrogen, R6Represents bromine;
or M represents methylene, R4,R5,R6,R7Represents hydrogen, R3Represents chlorine;
or M represents a methinyl radical R3,R4,R5,R6,R7Represents hydrogen;
or M represents methylene, R3,R6,R7Represents hydrogen, R4,R5Ring formation to form 1, 3-dioxole;
or M represents methylene, R3,R6,R7Represents hydrogen, R4,R5Represents chlorine;
or M represents methylene, R3,R4,R6,R7Represents hydrogen, R5Represents chlorine;
or M represents methylene, R3,R4,R6,R7Represents hydrogen, R5Represents a methyl group;
or M represents methylene, R3,R4,R6,R7Represents hydrogen, R5Represents fluorine;
or M represents methylene, R3,R4,R5,R7Represents hydrogen, R6Represents chlorine;
or M represents methylene, R3, R4, R5, R7 represents hydrogen, R6 represents fluoro;
or M represents methylene, R4, R5, R6, R7 represents hydrogen, R3 represents methyl;
or M represents methylene, R3,R4,R6,R7Represents hydrogen, R5Represents a benzene ring;
or M represents methylene, R3,R4,R6Represents hydrogen, R5,R7Represents chlorine;
or M represents methylene, R3,R4,R5,R6Represents hydrogen, R7Represents chlorine;
or M represents methylene, R3,R5,R7Represents hydrogen, R4,R6Represents fluorine;
or M represents methylene, R3,R4,R6,R7Represents hydrogen, R5Represents bromine;
or M represents methylene, R3,R4,R5,R6Represents hydrogen, R7Represents trifluoromethyl;
or M represents methylene, R3,R4,R5,R7Represents hydrogen, R6Represents trifluoromethyl;
or M represents methylene, R3,R4,R6,R7Represents hydrogen, R5Represents trifluoromethyl;
or M represents methylene, R3,R4,R5,R6Represents hydrogen, R7Represents bromine;
or M represents methylene, R3,R4,R5,R7Represents hydrogen, R6Represents a methyl group;
or M represents methylene, R3,R5,R7Represents hydrogen, R4,R6Represents chlorine.
3. The use of the sulfur-containing isocyanate compounds represented by the general formula I, II or III as set forth in claim 1 for preparing blue algae algicide, which is characterized in that: the sulfur-containing isocyanate compounds represented by the general formula I, II or III as claimed in claim 1 are used as the effective active ingredient.
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CN1356871A (en) * 1999-05-10 2002-07-03 伊洛弗制糖有限公司 Compsns. and process for nematode control
CN104628723A (en) * 2015-01-30 2015-05-20 华南农业大学 Banisterine benzoyl urea compounds and preparation method and application thereof

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