CN101161630A - Dialkyl diethylenetriamine and organic acid salt and uses thereof - Google Patents
Dialkyl diethylenetriamine and organic acid salt and uses thereof Download PDFInfo
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Abstract
The present invention relates to dialkyl-diethylenetriamine, in the formula of which R=CnH2n+1alkyl, n=8-18; Z=NH, NR; R<1>=H, R; Z<1>=NHR, as well as salts of organic acids and use of agricultural fungicide. The organic acids include chloroacetic acids, C2-8alkyl acid, amino acids, C2-4 alkyl-dibasic acid, lactic acid, salicylic acid, benzoic acid, hydroxyl benzoic acid, etc; all the amines and the organic acid salt thereof with the content between 10 percent to 99 percent can be used as agricultural fungicide, and widely used for prevention and treatment of plant diseases caused by fungi, bacteria, and virus, for example, the rot disease of fruit trees, the mosaic virus disease, the perforation disease, the gummosis disease , the mouldy heart disease, and the scab disease of the fruit tree; virus diseases and the rot disease of vegetables; and virus diseases and the wilt disease of the tobacco, the water melon and the muskmelon; and the wilt disease of cotton.
Description
Technical field
The present invention relates to dialkyl group diethylenetriamine and organic acid salt thereof and application.
Background technology
Along with expanding economy, growth in the living standard, people are to protecting healthy more and more attention, and to green food, the demand of pollution-free food is increasing.Central authorities require " greatly developing green food and pollution-free food ".Therefore, efficient, the low toxicity of research and development, green nuisance free pesticide are imperative.After the nineties, domestic 46 agricultural chemicals producers have applied for registration of aqua sterilant " octicin solution ".This medicine wide spectrum, efficient, low toxicity, has protection, interior suction and osmosis.Control fruit tree putrefaction disease, root rot, fruit tree, vegetables, tobacco leaf virus disease, the cotton spoting verticillium wilt effect is remarkable, has received good economic benefits and social benefit.The composition of " but octicin solution " can't be determined so far, can't carry out the agricultural chemicals staking-out work.
Summary of the invention
The objective of the invention is to overcome the shortcoming of prior art, a kind of dialkyl group diethylenetriamine and organic acid salt thereof are provided, said composition can be used as disinfectant use in agriculture, is widely used in the control of the Plant diseases that is caused by fungi, bacterium, virus, has wide spectrum, characteristics of high efficiency.
The invention provides a kind of dialkyl group diethylenetriamine, shown in general formula (I):
R=C wherein
nH
2n+1, n=8-18; Z=NH or NR; R
1=H or R; Z
1=NHR.
The invention provides a kind of dialkyl group diethylenetriamine organic acid salt, described dialkyl group diethylenetriamine is shown in general formula (I), and organic acid is selected from chloracetic acid, C
2-8Alkyl acid, amino acid, C
2-4Alkyl dicarboxylic acid, lactic acid, Whitfield's ointment, phenylformic acid, one of hydroxy-benzoic acid.
The invention provides a kind of composition, contain compound or its organic acid salt of general formula (I).
Composition provided by the invention is widely used in the control of the Plant diseases that is caused by fungi, bacterium, virus as disinfectant use in agriculture.The weight percentage of active ingredient is 10% in the composition---90%, comprise acceptable liquid or solid carrier at least a agricultural in the composition.
General formula compound of the present invention (I) can be prepared by following method:
Synthesizing of many alkyl diethylenetriamine
With diethylenetriamine and haloalkane (RX:R=C
nH
2n+1, n=8-18; X=Cl, B
r, I) with 3-4mol: the proportioning of 2-3mol, at 180 ℃-70 ℃, reacted 4-8 hour, cool to room temperature, standing over night is isolated the diethylenetriamine halogenation hydrogen salt of generation, the reaction solution underpressure distillation many alkyl diethylenetriamine, use toluene----ethyl alcohol recrystallization, pure product.
Synthesizing of many alkyl diethylenetriamine organic acid salt
In reaction flask with many alkyl diethylenetriamine and organic acid with the mixed of 1mol: 3mol in toluene or alcohol, in 80 ℃-60 ℃, reacted 2-4 hour, steam partial solvent, cooling crystallization filters, solid salt is with toluene or pure recrystallization, pure product.
The intermediate dialkyl group diethylenetriamine that the present invention obtains uses separately has sterilization effect, and sterilization effect is higher than his formed organic acid salt.
Description of drawings
Fig. 1 N, N "-infrared spectrogram of di-n-octyl diethylenetriamine (H-15) sample.
Fig. 2 .1N, N "-di-n-octyl diethylenetriamine (H-15) sample
1H NMR collection of illustrative plates (CDCl
3, 25 ℃).
Fig. 2 .2 N, N "-the local amplification of di-n-octyl diethylenetriamine (H-15) sample
1H NMR collection of illustrative plates (CDCl
3, 25 ℃).
Fig. 3 N, N "-di-n-octyl diethylenetriamine (H-15) sample
13C NMR collection of illustrative plates (CDCl
3, 25 ℃).
Fig. 4 N, N "-di-n-octyl diethylenetriamine (H-15) sample
13C-DEPT-135 composes (CDCl
3, 25 ℃)
Fig. 5 N, N "-the TIC spectrogram of di-n-octyl diethylenetriamine (H-15) sample.
Fig. 6 N, N "-mass spectrum of di-n-octyl diethylenetriamine (H-15) sample.
Fig. 7 N, N "-the DSC collection of illustrative plates of di-n-octyl diethylenetriamine (H-15) sample.
Fig. 8 N, N "-the TG/DTG collection of illustrative plates of di-n-octyl diethylenetriamine (H-15) sample and the superimposed collection of illustrative plates of DSC.
The infrared spectrogram of Fig. 9 sample RI-2.
Figure 10 sample RI-2's
1H NMR composes (CD
3OD, 25 ℃).
Figure 11 sample RI-2's
13C NMR composes (CD
3OD, 25 ℃).
Figure 12 sample RI-2's
13C-DEPT composes (CD
3OD, 25 ℃).
Figure 13 sample RI-2's is quantitative
13C NMR (zgig30, inverted gated decoupling) composes (CD
3OD, 25 ℃).
Figure 14 sample RI-2's
1H-
1HCOSY composes (CD
3OD, 25 ℃).
The hsqc spectrum of Figure 15 sample RI-2 (CD3OD, 25 ℃).
HMBC spectrum (the CD of Figure 16 .1 sample RI-2
3OD, 25 ℃).
The HMBC spectrum enlarged view (CD of Figure 16 .2 sample RI-2
3OD, 25 ℃).
Embodiment
1, reaction principle
2, test portion
Infrared spectra (IR) is used the KBr compressing tablet, and the U.S. NEXUS870 of Nicolet company type Fourier transform infrared spectrometer detects; Nucleus magnetic resonance (NMR) Bruker-AV500 type NMR spectrometer with superconducting magnet detects; The test of the German Ai Leman EL-III of ultimate analysis (EA) type elemental analyser; The test of differential scanning calorimetric (DSC) TA910S type differential scanning calorimeter; Thermogravimetric/difference quotient thermogravimetric (TG/DTG) U.S. TA company's T GA2950 instrument test; Organic mass spectrometry (MS) day island proper Tianjin GC-MS-2010QP gas chromatograph-mass spectrometer test.
2.1 N, N " synthesizing of di-n-octyl diethylenetriamine (H-15):
Systematic naming method: N
1-n-octyl-N
2-[2-(positive hot amino) ethyl]-1
2.1.1 raw material (seeing Table 1)
Table 1 synthesizes the H-15 raw material
| Title | Rank | Purity | The place of production |
| Toluene | AR | 99.5％ | Xi'an chemical reagent factory |
| Dehydrated alcohol | AR | 99.7％ | Xi'an chemical reagent factory |
| Diethylenetriamine | AR | 98％ | Xi'an chemical reagent factory |
| Sodium hydroxide | AR | 96.0％ | The rich power laboratory in Xi'an |
| Bromooctane | AR | 99％ | Wuxi Ao Teling clean-out system Science and Technology Ltd. |
2.1.2 experimental implementation
In the 500mL four-hole bottle, add diethylenetriamine 125.3g (98%, 1.2mol), be warmed up to 175 ℃, under agitation, dripping bromine octane 156.1g (99%, 0.8mol), the rate of addition control reaction temperature is at 175 ℃～180 ℃, drip off material after, at 180 ℃ of stirring reaction 4h, the cooling standing over night is separated the hydrogen bromide diethylenetriamine salt of removing generation and (is added a certain amount of NaOH and ethanol, after the heat fused, diethylenetriamine and NaBr are reclaimed in distillation), add 25g KOH in the reaction solution, stirring at room 2h filters, the filtrate decompression distillation, collect 180 ℃～185 ℃/30Pa～40Pa cut, ethanol-toluene repeated multiple times recrystallization draws mica shape white crystals, 62.3 ℃ of mp (digital fusing point instrument, capillary tube technique).
A. gas-chromatography
Chromatographic column: DB-1, long 30 meters, internal diameter 0.32mm, thickness 0.25 μ m
Post oven temperature, degree: 180 ℃ of initial temperatures, temperature programming: 10 ℃/min, 280 ℃ of outlet temperatures keep 30min.
Temperature of vaporization chamber: 290 ℃
Detector: FID, 300 ℃ of temperature
Solvent: methyl alcohol
Splitting ratio: 30
Analytical procedure: area normalization method
H-15 is pure: 99.6%
B. infrared spectra (IR) (see figure 1)
Instrument model: German Brooker company's T ENSOR27 type infrared spectrometer;
Test condition: 4000cm
-1～400cm
-1Measurement range, 4cm
-1Resolving power, 16 scanning;
Sample preparation methods: pellet technique.
KBr, v/cm
-1: 3277,3128 (vNH, m, B); 770,880 (δ NH, w, m, B); 2819 (vNH, m), 1486,1403 (w), 1136 (vC-N m), is respectively-CH for δ CH, m
2-N-CH
2-characteristic group spectrum; 2956,2875 (vCH, w, m), 1380 (δ CH, w) CH such as grade
3Middle spectrum; 2917,2848 (m), 1472 (δ CH m) is respectively CH for vCH, s
2
n, n＞4; 719 (w, CH
2Rocking vibration).
c.
1H NMR(CDCl
3)
Instrument model: Bruker-AV500 type superconduction nuclear magnetic resonance spectrometer
Experimental technique and condition: get an amount of N, N "-di-n-octyl diethylenetriamine (H-15) sample is in Φ 5 nuclear-magnetism sample hoses, with 0.5mL heavy hydrogen chloroform (CDCI
3) dissolving, then sample hose is placed magnet, survey it with the standard pulse sequence of Bruker
1H NMR,
13C NMR spectrum and relevant spectrum (see Fig. 2 .1, Fig. 2 .2, Fig. 3, Fig. 4).
1H NMR observing frequency is 499.933MHz,
13C NMR observing frequency is 125.72MHz.Probe temperature is 25 ℃.
1The interior mark of H NMR TMS (δ 0),
1Mark CDCI in the H NMR
3(δ 77.16).
NH and 1.5H have been removed
26 active H such as O, (6H, t), (8H, m), (4H, t), (4H, m), (2OH m), has 42 hydrogen atoms to δ 1.2-1.4 to δ 1.42-1.51 to δ 2.59 to δ 2.69-2.78 to δ 0.88, and this and predetermined structure are in full accord.
13C NMR (CDCl
3):
13Remove the CDCl of δ 277.16 (t) in the C NMR spectrum
3Solvent peak also has 10 peaks in addition, and the carbonatoms of predetermined molecules is 20, is illustrated as symmetrical structure; The DEPT-135 spectrum of H-15,1 posivtive spike (CH
3) and 9 negative peak (CH
2) also consistent with predetermined molecules.By
1H,
13C NMR thinks that the structure of H-15 is.
D. organic mass spectrometry (M) (is seen Fig. 5, Fig. 6)
Instrument model: day island proper Tianjin GC-MS-2010QP gas chromatograph-mass spectrometer.
Experiment condition: molecular weight sweep limit 34-800Da, 150 ℃-300 ℃ of temperature, the 10 ℃/min that heats up, 70EV, solvent THF.
High quality series ion is that 289,267,228,185 grades are that molion is lost the cracked positive ion that obtains behind the rational fragmention in the spectrogram.The very strong due ionization series of saturated fatty amine compound is arranged, C in the spectrogram
nH
2n+1The even number fragment m/z44 of N type, 58,72,86 etc.; The extra best best ion is m/z326 in the collection of illustrative plates, is that H-15 loses [M-H] that a proton becomes
+Ion, its molecular weight is 327 as can be known, contains the odd number nitrogen-atoms in the molecule, the C-C bond rupture that links to each other with N, owing to help eliminating than large-substituent, the m/z142 and the m/z185 of generation are easy, m/z142 and m/z185 abundance are higher, and are complementary ion, illustrate that molecular weight is 327.
E. ultimate analysis (EA)
The predetermined molecules formula C of censorship H-15
20H
45N
31.5H
2O, its results of elemental analyses such as table 2, its C, H, N test result and theoretical value basically identical.
The results of elemental analyses of table 2 H-15
| Element term | Test mass mark/% | Test mass mark/% | Theoretical Mass mark/% |
| C | 67.81 | 67.61 | 67.74 |
| H | 14.04 | 14.06 | 13.64 |
| N | 11.82 | 11.83 | 11.85 |
F.DSC tests (see figure 7)
Instrument model: TA9105 type differential scanning calorimeter
Test condition: 10 ℃ of min of temperature rise rate
-1, nitrogen flow: 50mLmin
-1
Range of measuring temp: 40 ℃～370 ℃
The H-15 sample has the fusing endotherm(ic)peak at about 62 ℃, and is constant substantially from the melting peak temperature of three different experimental conditions, but initial decomposition peak is different, sorts to be common pond under common pond＜2MPa under the normal pressure＜normal pressure lower seal pond.Second endotherm(ic)peak is because pressurization is postponed endotherm(ic)peak.The H-15 sample may be a dehydration-melting process.
G. thermogravimetric/difference quotient thermogravimetric test
Instrument model: U.S. TA company's T GA2950
Test condition: temperature rise rate is 10 ℃ of min
-1, be heated to 400 ℃, nitrogen flow: 100mLmin
-1
Find out at 51.34 ℃ that from accompanying drawing 8 H-15 TG/DTG a weightless peak is arranged, weight loss is 7.44%, is illustrated as to lose crystal water and melting process, and H-15 should contain 1.5 crystal water.
Be that example illustrates amine and organic acid building-up process with chloracetic acid below, other compounds can make by similar method.
3.1 N, N " synthesizing of di-n-octyl diethylenetriamine trichloroacetate (RI-2)
Systematic naming method: N
1-n-octyl-N
2-((2-n-octyl amino) ethyl)-1,2-quadrol trichloroacetate
3.2.1 raw material (seeing Table 3)
Table 3
| Title | Rank | Purity | The place of production |
| Mono Chloro Acetic Acid | AR | 99.5％ | Ni Huaxueshijichang is sent in Zhengzhou |
| Toluene | AR | 99.5％ | Xi'an chemical reagent factory |
| Dehydrated alcohol | AR | 99.7％ | Xi'an chemical reagent factory |
| H-15 | 99.0％ | Self-control (content 91.37%) |
3.2.2 experimental implementation
Agitator is being housed, thermometer, add N in the 500mL four-hole boiling flask of dropping funnel and reflux exchanger; N "-di-n-octyl diethylenetriamine 35.6g (self-control, content 91.37%, purity 99% is 0.1mol) with dehydrated alcohol 130mL, be warmed up to 30 ℃～36 ℃, under agitation, drip 31.5g Mono Chloro Acetic Acid (analytical pure, 99% from dropping funnel, 0.33mol) be dissolved in the solution in the 150ml dehydrated alcohol, after dripping off, behind 80 ℃ of backflow 4h, normal pressure steams partial solvent, naturally the cooling crystallization, filter, get white, needle-shaped crystals with the dehydrated alcohol recrystallization, mp109.1 ℃ of-109.7 ℃ of (digital fusing point instrument, capillary tube technique), purity 99% (nonaqueous titration).
Infrared spectra (IR) (KBr, v/cm
-1) (see figure 9): 2949,2925,2914,2851 (w, m, v-CH); 1468,1415 (m, δ-CH); 2696,2352 (m, Vbr ,-NH
2 +); 1561,1393,1384 (s, vCOO
-); 1257 (s, vC-O); 674 (m, δ COO
-); 776 (m, vC-Cl); 3005 (w, vCH).
1HNMR (CD
3OD) (see figure 10): δ 4.02 (6H, s), δ 3.10 (4H, t), and δ 3.00 (4H, t), δ 2.93 (4H, t), δ 1.72 (4H, m), and δ 1.30-1.38 (2OH, m), δ 0.904 (6H, t), the proton total mark is 48, total proton number is 54, removes 6 reactive hydrogens, meets the total proton number of predetermined structure of R1-2.
13C NMR (CD
3OD) (RI-2's
13C NMR accompanying drawing 13--15): with numeral the structural formula skeleton is made a mark for belonging to conveniently:
Compound R I-2 structure
13Remove outside the solvent peak among the C NMR, have 12 sharp-pointed spectral lines (wherein a spectral line is in solvent peak), and 26 carbon atoms are arranged among the compound R I-2, illustrate that molecule has symmetrical structure,, set δ in quantitative carbon spectrum
C173.6Integration is 3, can obtain the integrated value of all the other spectral lines, and amounting to carbonatoms is 26, and this structure with R1-2 is consistent; δ in the DEPT-135 carbon spectrum (seeing Figure 12)
C173.475Blackout, it belongs to C-14 (C among the C=O), δ
C14.429Signal makes progress, and it belongs to C-12 (CH
3Middle C), all the other 9 peak-to-peak signals are downwards CH
2Hsqc spectrum (seeing Figure 15) and HMBC (seeing Figure 16 .1, Figure 16 .2) spectrum can find
13C with
1H is directly related, these results further confirm the RI-2 structure correct (it with
1H signal resolution such as table 4).Ultimate analysis (EA): (German Ai Leman EL-III type elemental analyser) RI-2 predetermined molecules formula is C
26H
54Cl
3N
3O
6, molecular weight is 611.08, its results of elemental analyses such as table 5.
The NMR side test result resolution table of table 4 RI-2 sample
| NO. | δc(J/Hz) | δ H(J/Hz) | COSY | | HMBC | |
| 2/2′ | 45.8 | 2.93(4H，t) | H-3 | CH 2 | H-3，H-2′ | |
| 3/3′ | 47.6 | 3.10(4H，t) | H-2 | CH 2 | H-2 | |
| 5/5′ | 48.9 | 3.01(4H，t) | H-6 | CH 2 | H-6，H-3 | |
| 6/6′ | 27.2 | 1.72(4 H，m，) | H-5，H-7 | CH 2 | H-5 | |
| 7/7′ | 27.7 | 1.28～1.45(4H，m) | H-6 | CH 2 | H-6 | |
| 8/8′ | 30.2 * | 1.28～1.45(4H，m) | ** | CH 2 | H-9 |
The results of elemental analyses of table 5 RI-2
| Element term | Test elements mass percent (%) | Theoretical Mass percentage ratio (%) |
| C | 57.50 | 51.06 |
| H | 9.01 | 8.67 |
| N | 6.88 | 6.87 |
The element mass percent basically identical of the mass percent of the element of surveying and theoretical amount is illustrated as predetermined structure.
4, result and analysis
4.1 40% octicin solution mother liquor and RI-2 that Jia Kenongization company limited in Xi'an is provided send biotechnology research test center of The Institute for the Control of Agrochemicals of the Ministry of Agriculture,PRC to detect, the result shows (table 6,7,8,9) under isolated condition, and 40% octicin solution mother liquor, RI-2 and the former medicine of 97% thiophanate_methyl all have stronger restraining effect to Valsa mali.Concentration is that 40.00mg/L octicin solution mother liquor and RI-2 and concentration are that the former medicine of 97% thiophanate_methyl of 3.00mg/L has all reached more than 50% the inhibiting rate of germ mycelial growth.
40% octicin solution mother liquor, RI-2 and the former medicine of 97% thiophanate_methyl are respectively 33.3696mg/L, 33.7294mg/L, and 2.1906mg/L to concentration in effective inhibition of Valsa mali mycelial growth.
Table 6 40% octicin solution mother liquor suppresses situation to the mycelial growth of Valsa mali
| Drug concentration (mg/L) | CK | 50.00 | 40.00 | 20.00 | 10.00 | 5.00 |
| Bacterium colony increases diameter *(mm) | 5.75 | 2.03 | 2.73 | 3.02 | 3.67 | 4.98 |
| Proofread and correct inhibiting rate (%) | ---- | 64.64 | 52.46 | 47.54 | 36.23 | 13.33 |
*Be 3 multiple mean values.
Table 7 RI-2 suppresses situation to the mycelial growth of Valsa mali
| Drug concentration (mg/L) | CK | 50.00 | 40.00 | 20.00 | 10.00 | 5.00 |
| Bacterium colony increases diameter *(mm) | 5.75 | 1.32 | 2.57 | 3.88 | 4.25 | 5.17 |
| Proofread and correct inhibiting rate (%) | ---- | 77.10 | 55.36 | 32.46 | 26.09 | 10.14 |
*Be 3 multiple mean values.
The former medicine of table 8 97% first tomb thiophanate suppresses situation to the mycelial growth of Valsa mali
| Drug concentration (mg/L) | CK | 5.00 | 4.00 | 3.00 | 2.00 | 1.00 |
| Bacterium colony increases diameter *(mm) | 5.75 | 0.27 | 1.23 | 2.53 | 3.60 | 4.80 |
| Proofread and correct inhibiting rate (%) | --- | 95.36 | 78:55 | 55.94 | 37.39 | 16.52 |
*Be 3 multiple average bit.
Table 9 40% octicin solution mother liquor, RI-2 and the former medicine of 97% first tomb thiophanate
Toxicity Determination result to Valsa mali
| The toxicity regression curvilinear equation | Relation conefficient | EC 50(reality) | |
| Medicament | (Y＝A+BX) | (r) | (mg/L) |
| 40% octicin solution mother liquor | Y＝1.9183+2.0230X | 0.9909 | 33.3696 |
| RI-2 | Y＝0.9359+2.6598X | 0.9552 | 33.7294 |
| The former medicine of 97% thiophanate_methyl | Y＝3.7996+3.5249X | 0.9526 | 2.1906 |
Measured the N that Xi'an Jia Kenongization company limited provides 4.2 biotechnology research test center of The Institute for the Control of Agrochemicals of the Ministry of Agriculture,PRC is the contrast medicament with RI-2, " a dioctyl diethylenetriamine and Mono Chloro Acetic Acid are to the stripped bacteriostatic activity of Valsa mali for N.Test-results shows, N, N " bacteriostatic activity of the relative RI-2 of a dioctyl diethylenetriamine is stronger; and the relative RI-2 of Mono Chloro Acetic Acid does not have tangible bacteriostatic activity to Valsa mali under equal drug concentration, but the relative inhibition to the Valsa mali mycelial growth has reached more than 80% under the high drug concentration of 500.00mg/L.
The result shows (table 10,11,12,13) simultaneously, and under isolated condition, " the dioctyl diethylenetriamine all has stronger restraining effect to Valsa mali for RI-2 and N, N.Concentration is that 40.00mg/L RI-2 and concentration are the N of 15.00mg/L, and " the dioctyl diethylenetriamine has all reached more than 50% the inhibiting rate of germ mycelial growth N.Mono Chloro Acetic Acid to Valsa mali mycelial growth restraining effect a little less than, when drug concentration 300.00mg/L, do not have the obvious suppression effect yet.
N, " dioctyl diethylenetriamine and RI-2 are respectively 11.3678mg/L and 26.1007mg/L to concentration in effective inhibition of Valsa mali mycelial growth to N.
Table 10N, " the dioctyl diethylenetriamine suppresses situation to the mycelial growth of Valsa mali to N
| Drug concentration (mg/L) | CK | 30.00 | 25.00 | 20.00 | 15.00 | 10.00 |
| Bacterium colony increases diameter *(mm) | 56.50 | 8.00 | 10.12 | 16.67 | 21.67 | 45.43 |
| Proofread and correct inhibiting rate (%) | - | 85.84 | 82.01 | 70.50 | 61.65 | 30.83 |
*Be 3 multiple mean values.
Table 11 Mono Chloro Acetic Acid suppresses situation to the mycelial growth of Valsa mali
| Drug concentration (mg/L) | CK | 500.00 | 400.00 | 300.00 | 200.00 | 100.00 |
| Bacterium colony increases in the diameter *(mm) | 57.00 | 10.67 | 39.17 | 56.67 | 60.50 | 57.00 |
| Proofread and correct inhibiting rate (%) | - | 81.29 | 31.29 | 0.58 | -6.14 | 0 |
*Be 3 multiple mean values.
Table 12 RI-2 suppresses situation to the mycelial growth of Valsa mali
| Drug concentration (mg/L) | CK | 50.00 | 40.00 | 20.00 | 10.00 | 5.00 |
| Bacterium colony increases diameter *(mm) | 56.50 | 11.33 | 24.00 | 28.33 | 34.17 | 44.00 |
| Proofread and correct inhibiting rate (%) | - | 79.94 | 57.52 | 49.85 | 39.53 | 22.12 |
*Be 3 multiple mean values.
Table 13 RI-2, N, N " dioctyl diethylenetriamine and Mono Chloro Acetic Acid
Toxicity Determination result to Valsa mali
| Medicament | Toxicity regression curvilinear equation (Y=A+BX) | ECSo | Relation conefficient (r) | ECso (erg/L) 95% fiducial limit |
| N, N " dioctyl diethylenetriamine | Y＝12.3365+2.5231X | 11.3678 | 0.9945 | 10.55-12.25 |
| Mono Chloro Acetic Acid | - | - | - | - |
| RI-2 | Y＝2.1050+2.0436X | 26.1007 | 0.9529 | 21.27-32.03 |
Claims (5)
1. dialkyl group diethylenetriamine, shown in general formula (I):
R=C wherein
nH
2n+1, n=8-18; Z=NH or NR; R
1=H or R; Z
1=NHR.
2. a dialkyl group diethylenetriamine organic acid salt is characterized in that described dialkyl group diethylenetriamine shown in general formula (I), and organic acid is selected from chloracetic acid, C
2-8Alkyl acid, amino acid, C
2-4Alkyl dicarboxylic acid, lactic acid, Whitfield's ointment, phenylformic acid, one of hydroxy-benzoic acid.
3. composition is characterized in that containing compound or its organic acid salt of general formula (I).
4. composition as claimed in claim 3, the weight percentage that it is characterized in that active ingredient in the composition is 10%---90%, comprise acceptable liquid or solid carrier at least a agricultural in the composition.
5. the described composition of claim 3 is as the application of disinfectant use in agriculture.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2007100188754A CN101161630A (en) | 2007-10-16 | 2007-10-16 | Dialkyl diethylenetriamine and organic acid salt and uses thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2007100188754A CN101161630A (en) | 2007-10-16 | 2007-10-16 | Dialkyl diethylenetriamine and organic acid salt and uses thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101161630A true CN101161630A (en) | 2008-04-16 |
Family
ID=39296621
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2007100188754A Pending CN101161630A (en) | 2007-10-16 | 2007-10-16 | Dialkyl diethylenetriamine and organic acid salt and uses thereof |
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| CN (1) | CN101161630A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102578089A (en) * | 2011-12-15 | 2012-07-18 | 黄廷纪 | Smearing preparation for controlling fruit tree rotten disease |
| CN104628602A (en) * | 2015-02-05 | 2015-05-20 | 宋和璇 | Tetramethyl diethylenetriamine formate compound as well as preparation method and application thereof |
| CN104738047A (en) * | 2015-03-19 | 2015-07-01 | 海利尔药业集团股份有限公司 | Bactericidal composition containing Xinjunan acetate and bupirimate |
| CN113476651A (en) * | 2021-07-12 | 2021-10-08 | 南通美韦德生命科学有限公司 | Antibacterial resin for bone fixation |
| CN113620812A (en) * | 2021-08-27 | 2021-11-09 | 山东胜邦绿野化学有限公司 | Preparation method of N, N' -dioctyl diethylenetriamine standard substance |
| CN115057784A (en) * | 2022-07-13 | 2022-09-16 | 山东胜邦绿野化学有限公司 | Method for treating octyl trichlamide wastewater |
-
2007
- 2007-10-16 CN CNA2007100188754A patent/CN101161630A/en active Pending
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102578089A (en) * | 2011-12-15 | 2012-07-18 | 黄廷纪 | Smearing preparation for controlling fruit tree rotten disease |
| CN104628602A (en) * | 2015-02-05 | 2015-05-20 | 宋和璇 | Tetramethyl diethylenetriamine formate compound as well as preparation method and application thereof |
| CN104628602B (en) * | 2015-02-05 | 2016-08-17 | 宋和璇 | Tetramethyl diethylenetriamine base formiate compound and its preparation method and application |
| CN104738047A (en) * | 2015-03-19 | 2015-07-01 | 海利尔药业集团股份有限公司 | Bactericidal composition containing Xinjunan acetate and bupirimate |
| CN113476651A (en) * | 2021-07-12 | 2021-10-08 | 南通美韦德生命科学有限公司 | Antibacterial resin for bone fixation |
| CN113620812A (en) * | 2021-08-27 | 2021-11-09 | 山东胜邦绿野化学有限公司 | Preparation method of N, N' -dioctyl diethylenetriamine standard substance |
| CN113620812B (en) * | 2021-08-27 | 2023-09-22 | 山东胜邦绿野化学有限公司 | Preparation method of N, N' -dioctyl diethylenetriamine standard |
| CN115057784A (en) * | 2022-07-13 | 2022-09-16 | 山东胜邦绿野化学有限公司 | Method for treating octyl trichlamide wastewater |
| CN115057784B (en) * | 2022-07-13 | 2024-04-05 | 山东胜邦绿野化学有限公司 | Method for treating waste water of octaworking |
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