CN1613852A - Cesium triazoleamide compounds and their preparation and use - Google Patents
Cesium triazoleamide compounds and their preparation and use Download PDFInfo
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Abstract
This invention relates to triazolacylamine compound containing selenium and its preparation and use. It is prepared by: using substituted amine as start material, preparing its diazo salt, making the said salt condensed with triazoselenophen to obtain aromatic triazoselenide, oxidizing it to obtain triazoselesulfoxide (triazosulfone), condensing triazo sulfone and sulfoxide and aromatic triazoselenide with N,N dialkyl formyl chloride selectively to obtain target products; or oxidizing triazoselenide with dioxide to obtain triazo selenic acid, then preparing Cl selenide, condensing it with substituted phenol to obtain selenonyl triazophenate, condensing it with N,N dialkyl formyl chloride to obtain target product. It can be used as herbicide for crop with good selective ability and safety.
Description
Technical field
The present invention relates to a kind of contain selenium triazolylamide compounds and preparation and application.
Background technology
Weedicide is one of important pesticide variety, plays important effect in agriculture production.Weeds fight for growth and the growth that nutrient in sunlight, moisture and the soil has seriously influenced crop with farm crop, have reduced output and the quality of crop.Many weeds still are the host of farm crop germ, virus and insect, easily cause spreading in crop of disease and pest, and therefore, weedicide plays important effect in plant protection.
At present, mainly to be divided into two classes be sulphonyl triazole species acid amides (CH-900:JP07173020 to the compound that is applied to weedicide; Brighton Crop Prot.Conf-weeds, Vol 3, and 927-8) (CH-2000:JP 05004976 for class and sulfonyl ester triazole species acid amides; JP 05140124), the weeding activity of this two compounds is than higher, but there is certain poisoning in it to farm crop.Therefore, develop a kind of high herbicidal activity that both had, having good security and selective herbicide again becomes the focus that people pay close attention to, and this also becomes the technical issues that need to address of the present invention equally.
Summary of the invention
The present invention's design:
The contriver is by to existing structure and the active relation research that is applied to herbicidal compounds, discovery is with atomic radius and electronegativity and the very approaching selenium replacement sulfur of sulphur, can improve of the harm of existing corresponding sulfocompound to farm crop, also reduce simultaneously its residual in soil, thereby prevent its harm succession crop.
Technical scheme:
The said selenium triazolylamide compounds that contains of the present invention has following structure:
In the formula: R
1, R
2Be C
1～C
8Alkyl, preferred C
1～C
3Alkyl;
On behalf of five yuan or hexavalent, A contain 1～3 heteroatomic heterocycle or aromatic ring, preferred pyrazoles, pyridine, thiazole, pyrroles or benzene, and the best is a phenyl ring;
R represents A substitution in ring base, is hydrogen, halogen, alkyl, nitro, haloalkyl and/or alkoxyl group, and is preferred: 2-, 2-, 6-or 2-, 4-, the C that the 6-position replaces
1～C
4Alkyl; N=0,1,2 or 3.The method for preparing the compound of n in the compound of the present invention≤2 comprises the steps:
1) preparation of fragrant triazole selenide:
To replace amine (R-A-NH
2) be starting raw material, at first make diazonium salt through diazotization, then diazonium salt and the selenides condensation that makes obtained fragrant triazole selenide;
2) preparation of triazole selenium (Asia) sulfone:
Carry out oxidation and can make triazole selenium (Asia) sulfone obtained fragrant triazole selenide by step 1), wherein said oxidation can be adopted in the following method for oxidation a kind of,
(1) in Glacial acetic acid, uses hydrogen peroxide oxidation;
(2) in Glacial acetic acid, carry out oxidation as catalyzer with sodium wolframate;
(3) in tetrahydrofuran (THF), ether, ketone, Glacial acetic acid with plumbic acetate for making catalyzer, use hydrogen peroxide oxidation;
(4) Oxone with Du Pont carries out oxidation as oxygenant;
3) preparation of target product:
With N, N dialkyl group formyl chloride respectively with the fragrant triazole selenide that makes by step 1), by step 2) the triazole selenone or the triazole selenoxide that make carry out condensation reaction, makes target product.
The key step for preparing the compound of n=3 in the compound of the present invention is as follows:
At first selenides is made triazolyl selenic acid through hydrogen peroxide oxidation, it is prepared into corresponding acyl chlorides then, the acyl chlorides and substituted phenol (R-A-OH) condensation that make are obtained selenium acyl triazole phenolic ester, and at last with gained selenium acyl triazole phenolic ester and N, the condensation of N dialkyl group formyl chloride gets target product.
The reaction formula of the said compound of preparation the present invention is as follows:
Make weedicide compared with prior art with compound of the present invention, under the prerequisite that does not reduce weeding activity, the security and the selectivity of weedicide have been improved, it can or occur the selective herbicide of back as monocot crops (especially paddy rice, wheat and corn) or dicotyledonous crops (especially soybean, cotton and Sunflower Receptacle) before weeds occur, its concrete using method is identical with existing weedicide, is not giving unnecessary details at this.
Specific implementation method
The present invention is further illustrated below by embodiment, and the cited case does not limit protection scope of the present invention:
Embodiment 1
1-(N, N '-diethylamino) formyl radical-3-(1H-1,2,4-triazole) selenonyl-2,4,6-Three methyl Benzene synthetic.
(1) the seleno Urea,amino-synthetic:
Add the thiosemicarbazide that 24.5g (0.27mol) grinds in the 250ml single port flask, 150ml dehydrated alcohol and 16.8ml (0.27mol) methyl iodide, back flow reaction one hour.Obtain clear, colorless S-methyl thiosemicarbazide ethanolic soln.Under the ice bath, add sodium borohydride 15g (0.405mol) and selenium powder 21.32g (0.27mol) in the 500ml there-necked flask and mix.System through vacuumize and logical argon gas under, inject dehydrated alcohol 150ml, vigorous reaction.After reaction finished, deicing was bathed.In the S-methyl thiosemicarbazide ethanolic soln injection system that makes, room temperature reaction spends the night.Filter and use absolute ethanol washing, dry canescence seleno Urea,amino-, the productive rate 90% of getting.The dehydrated alcohol recrystallization gets colourless acicular crystal, 189-191 ℃ of decomposition.
(2) 1-formyl radical seleno Urea,amino-synthetic:
Add seleno Urea,amino-15g (0.108mol) and formic acid 25ml in 50ml single port flask, backflow 0.5hr is cooled to room temperature, and tame less water is filtered and the dry crystal that must have canescence metalluster.Productive rate 93%.The white plates crystal of dehydrated alcohol recrystallization, m.p.168-170 ℃.
(3) selenides is synthetic:
Add 1-formyl radical seleno Urea,amino-7.52g (0.045mol), potassium hydroxide 3.38g (0.068mol) and ethanol 70ml, backflow 1hr in the single port flask of 150ml.The adding concentrated hydrochloric acid is neutralized to PH6-7, filtering black powder shape solid after being cooled to room temperature.M.p.＞300℃。
(4) (2,4, the 6-trimethylphenyl) selenide-1H-1,2,4-triazole synthetic:
In the 100ml there-necked flask, add 2 6.08g (0.045mol), 30ml water and 12ml concentrated hydrochloric acid (0.14mol) drip the Sodium Nitrite 3.11g (0.045mol) that is dissolved in 10ml water down at 0 ℃.Drip Bi Fanying and get transparent diazonium salt solution half an hour.Under ice bath, add triazolyl selenium phenol 6.75g (0.0045mol), potassium hydroxide 3.38g (0.068mol) and dehydrated alcohol 70ml in the 250ml there-necked flask.Stir the above-mentioned diazonium salt solution of adding down, and react 5hr down at 0-5 ℃.Reaction solution transfers to neutral back with ethyl acetate extraction and concentrated extract, and silicagel column separates (ethyl acetate: sherwood oil=1: 1) get faint yellow solid.Productive rate 75%, M.p.181-182 ℃
(5) 1H-1,2,4-triazole selenonyl-(2,4, the 6-Three methyl Benzene) synthetic:
In 250ml single port flask, add (2,4, the 6-trimethylphenyl) selenide-1H-1,2,4-triazole 1.7g (0.0064mol) and 80ml anhydrous methanol, the Oxone7.86g (0.0128mol) that adds the damping fluid 30ml that is made into by Sodium phosphate dibasic and sodium hydroxide again and be dissolved in 15ml water under agitation reacts the 10min after-filtration and washs with anhydrous methanol.Concentrating filter liquor is transferred pH value 6-7, leaves standstill after-filtration and gets white crystal.91%, 230 ℃ of decomposition of productive rate.
(6) 1-(N, N '-diethylamino) formyl radical-3-(1H-1,2,4-triazole) selenonyl-2,4,6-Three methyl Benzene synthetic:
In 50ml single port flask, add 0.97g (0.00325mol) 1H-1,2,4-triazole selenonyl-(2; 4, the 6-Three methyl Benzene) and 25ml acetone, add Anhydrous potassium carbonate 1.6g (0.0116mol) and N again; N '-diethylamino formyl chloride 0.67g (0.005mol), room temperature reaction 5hr filters.Filtrate is used chloroform extraction, and chloroform is used the anhydrous sodium sulfate drying after-filtration mutually, concentrates.Silicagel column separates (ethyl acetate: sherwood oil 1: 1) get white solid.Productive rate 98%, M.p.155-157 ℃.MS (ESI) m/z:421 (M+Na
+), ultimate analysis: theoretical value C 48.37% H 5.58% N 14.10%, measured value C 48.44% H 5.56% N 14.13%.
Embodiment 2
Synthesizing of 1-(N, N '-diethylamino) formyl radical-3-(1H-1,2,4-triazole) selenium acyl ester group-(2,4, the 6-Three methyl Benzene)
(1) triazolyl selenic acid is synthetic:
In 100ml single port flask, add triazolyl selenium phenol 2.96g (0.02mol) and Glacial acetic acid 25ml dissolving.Slowly drip 30% hydrogen peroxide 20ml, room temperature reaction spends the night.Filter, with cold water washing and the dry white solid that gets.Productive rate 61%, M.p.52 ℃.
(2) triazolyl selenium acyl chlorides is synthetic:
In 50ml single port flask, add triazolyl selenic acid 1.96g (0.01mol) and sulfur oxychloride 25ml, react down at 40-45 ℃ and spend the night.The colourless liquid of underpressure distillation.Productive rate 85%.
(3) triazole selenium acyl ester group-(2,4, the 6-Three methyl Benzene) is synthetic:
Add 2,4 in 50ml single port flask, 6-trimethylphenyl phenol 0.68g (0.005mol) and the dissolving of 25ml chloroform drip triazolyl selenium acyl chlorides 0.98g (0.005mol).Room temperature reaction 10hr, recrystallizing methanol gets white crystals.Productive rate 92%, M.p.142-144 ℃.
(4) 1-(N, N '-diethylamino) formyl radical-3-(1H-1,2,4-triazole) selenium acyl ester group-(2,4, the 6-Three methyl Benzene) is synthetic:
In 50ml single port flask, add triazole selenium acyl ester group-2,4, the 6-Three methyl Benzene) 0.785g (0.0025mol), methylene dichloride 20ml and Anhydrous potassium carbonate 0.69g (0.005mol) drip N, N '-diethylamino formyl chloride 0.34g (0.0025mol).Room temperature reaction 10hr filters.Filtrate is used chloroform extraction, and chloroform is used the anhydrous sodium sulfate drying after-filtration mutually, concentrates.Silicagel column separates (ethyl acetate: sherwood oil 1: 1) get white solid.Productive rate 90%, M.p.52-54 ℃.MS (ESI) m/z:437 (M+Na
+), ultimate analysis: theoretical value C 46.49% H 5.36% N 13.55%, measured value C 46.47% H 5.38% N 13.60%.
Embodiment 3
Synthesizing of 1-(N, N '-diethylamino) formyl radical-3-(1H-1,2,4-triazole) seleninyl-(2,4, the 6-Three methyl Benzene)
(1) 1H-1,2,4-triazole seleninyl-(2,4, the 6-Three methyl Benzene) synthetic:
In 100ml single port flask, add (2,4, the 6-trimethylphenyl) selenide-1H-1,2,4-triazole (ginseng example 1) 1.34g (0.005mol) and Glacial acetic acid 30ml slowly drip 30% hydrogen peroxide 10ml.Room temperature reaction 10hr uses dichloromethane extraction, and extraction liquid concentrates and silicagel column separates (methyl alcohol: ethyl acetate=1: 8) get white solid.Productive rate 78%, M.p.202-204 ℃.
(2) 1-(N, N '-diethylamino) formyl radical-3-(1H-1,2,4-triazole) seleninyl-(2,4, the 6-Three methyl Benzene) is synthetic:
With above-mentioned synthetic (2,4, the 6-trimethylphenyl) seleninyl-1H-1,2, the 4-triazole is a raw material, obtains white solid according to (4) method in the example 2.Productive rate 87%, M.p.95-96 ℃.MS (ESI) m/z:405 (M+Na
+), ultimate analysis: theoretical value C 50.40% H 5.81% N 14.69%, measured value C 50.44% H 5.83% N14.72%.
Embodiment 4
Synthesizing of 1-(N, N '-diethylamino) formyl radical-3-(1H-1,2,4-triazole) seleninyl-(3-methyl-2-pyridine)
(1) (3-methyl-2-pyridyl) selenide base-1H-1,2,4-triazole synthetic:
With 3-methyl-2-pyridyl is raw material, according to synthetic (3-methyl-2-pyridyl) selenide base-1H-1 of example 1 method, 2,4-triazole;
(2) 1-(N, N '-diethylamino) formyl radical-3-(1H-1,2,4-triazole) seleninyl-(3-methyl-2-pyridine) is synthetic:
With (3-methyl-2-pyridyl) selenide base-1H-1,2, the 4-triazole is a raw material, obtains white solid according to example 4 methods.Overall yield 45%, M.p.75-76 ℃.MS (ESI) m/z:378 (M+Na
+), ultimate analysis: theoretical value C 44.07% H 4.84% N 19.77%, measured value C 44.04% H 4.86% N 19.82%.
Embodiment 5
Synthesizing of 1-(N, N '-diethylamino) formyl radical-3-(1H-1,2,4-triazole) seleno-(2,4, the 6-Three methyl Benzene)
With (2,4, the 6-trimethylphenyl) seleno-1H-1,2,4-triazole (ginseng example 1) is a raw material, according to (4) method in the example 2 obtain white solid.Productive rate 87%, M.p.73-74 ℃.MS (ESI) m/z:389 (M+Na
+), ultimate analysis: theoretical value C 52.60% H 6.07% N 15.34%, measured value C 52.64% H 6.05% N15.37%.
Embodiment 6
Synthesizing of 1-(N, N '-methylethyl amino) formyl radical-3-(1H-1,2,4-triazole) selenonyl-(2,4, the 6-Three methyl Benzene)
With (2,4, the 6-trimethylphenyl) selenonyl-1H-1,2,4-triazole (ginseng example 1) be a raw material, react with 1-(N, N '-methylethyl amino) formyl chloride, according to the method for example 1 obtain white solid.Productive rate 97%, M.p.154-155 ℃.MS (ESI) m/z:407 (M+Na
+), ultimate analysis: theoretical value C 47.00% H 5.26%N 14.62%, measured value C 47.03% H 5.27% N 14.59%.
Embodiment 7
Synthesizing of 1-(N, N '-methyl-propyl amino) formyl radical-3-(1H-1,2,4-triazole) selenonyl-(2,4, the 6-Three methyl Benzene)
With (2,4, the 6-trimethylphenyl) selenonyl-1H-1,2,4-triazole (ginseng example 1) be a raw material, react with 1-(N, N '-methyl-propyl amino) formyl chloride, according to the method for example 1 obtain white solid.Productive rate 97%, M.p.149-150 ℃.MS (ESI) m/z:421 (M+Na
+), ultimate analysis: theoretical value C 48.37% H 5.58%N 14.10%, measured value C 48.40% H 5.58% N 14.13%.
Embodiment 8
Synthesizing of 1-(N, N '-dimethylamino) formyl radical-3-(1H-1,2,4-triazole) selenonyl-(2,4, the 6-Three methyl Benzene)
With 1H-1,2,4-triazole selenonyl-(2,4, the 6-Three methyl Benzene) (ginseng example 1) be raw material, react with 1-(N, N '-dimethylamino) formyl chloride, according to the method for example 1 obtain white solid.Productive rate 93%, M.p.151-152 ℃.MS (ESI) m/z:393 (M+Na
+), ultimate analysis: theoretical value C 45.54% H 4.91%N 15.17%, measured value C 45.58% H 4.90% N 15.20%.
Embodiment 9
Synthesizing of 1-(N, N '-propyl group butyl amino) formyl radical-3-(1H-1,2,4-triazole) selenonyl-(2,4, the 6-Three methyl Benzene)
With 1H-1,2,4-triazole selenonyl-(2,4,6-Three methyl Benzene (ginseng example 1) be a raw material, react with 1-(N, N '-propyl group butyl amino) formyl chloride, according to the method for example 1 obtain white solid.Productive rate 95%, M.p.144-146 ℃.MS (ESI) m/z:463 (M+Na
+), ultimate analysis: theoretical value C 51.93% H 6.42%N 12.75%, measured value C 51.94% H 6.42% N 12.80%.
Embodiment 10
Synthesizing of 1-(N, N '-dipropyl amino) formyl radical-3-(1H-1,2,4-triazole) selenonyl-(2,4, the 6-Three methyl Benzene)
With 1H-1,2,4-triazole selenonyl-(2,4, the 6-Three methyl Benzene) (ginseng example 1) be raw material, react with 1-(N, N '-dipropyl amino) formyl chloride, according to the method for example 1 obtain white solid.Productive rate 94%, M.p.141-143 ℃.MS (ESI) m/z:449 (M+Na
+), ultimate analysis: theoretical value C 50.82% H 6.16%N 13.17%, measured value C 50.83% H 6.18% N 13.22%.
Embodiment 11
Synthesizing of 1-(N, N '-dibutylamino) formyl radical-3-(1H-1,2,4-triazole) selenonyl-(2,4, the 6-Three methyl Benzene)
With 1H-1,2,4-triazole selenonyl-(2,4, the 6-Three methyl Benzene) (ginseng example 1) be raw material, react with 1-(N, N '-dibutylamino) formyl chloride, according to the method for example 1 obtain white solid.Productive rate 90%, M.p.139-141 ℃.MS (ESI) m/z:477 (M+Na
+), ultimate analysis: theoretical value C 52.98% H 6.67%N 12.36%, measured value C 53.00% H 6.66% N 12.38%.
Embodiment 12
Synthesizing of 1-(N, N '-methyl butyl amino) formyl radical-3-(1H-1,2,4-triazole) selenonyl-(2,4, the 6-Three methyl Benzene)
With 1H-1,2,4-triazole selenonyl-(2,4, the 6-Three methyl Benzene) (ginseng example 1) be raw material, react with 1-(N, N '-methyl butyl amino) formyl chloride, according to the method for example one obtain white solid.Productive rate 91%, M.p.141-142 ℃.MS (ESI) m/z:435 (M+Na
+), ultimate analysis: theoretical value C 49.64% H 5.88%N 13.62%, measured value C 49.68% H 5.87% N 13.59%.
Embodiment 13
Synthesizing of 1-(N, N '-diethylamino) formyl radical-3-(1H-1,2,4-triazole) selenonyl-(2, the 6-dimethyl benzene)
(1) (2, the 6-3,5-dimethylphenyl) selenide-1H-1,2,4-triazole synthetic
With 2, the 6-xylidine is a raw material, obtains yellow solid according to the method for (4) in the example 1.Productive rate 76%, M.p.179-180 ℃
(2) 1-(N, N '-diethylamino) formyl radical-3-(1H-1,2,4-triazole) selenonyl-(2, the 6-dimethyl benzene) is synthetic
With (2, the 6-3,5-dimethylphenyl) selenide-1H-1,2, the 4-triazole is a raw material, the method that reaches (6) according to (5) in the example 1 obtains white solid.Productive rate 80%, M.p.152-153 ℃.MS (ESI) m/z:407 (M+Na
+), ultimate analysis: theoretical value C 47.00% H 5.26% N 14.62%, measured value C 47.05% H 5.26% N 14.61%.
Embodiment 14
1-(N, N '-diethylamino) formyl radical-3-(1H-1,2,4-triazole) selenium acyl ester group-(2, the 6-dimethyl benzene)
With 2,6-dimethyl phenylamino is a starting raw material, gets white solid according to example 2 methods.Productive rate 85%, M.p.59-60 ℃.MS (ESI) m/z:423 (M+Na
+), ultimate analysis: theoretical value C 45.12% H 5.05% N14.03%, measured value C 45.14% H 5.07% N 14.08%.
Embodiment 15
1-(N, N '-diethylamino) formyl radical-3-(1H-1,2,4-triazole) selenonyl-(2, the 4-dimethyl benzene)
(1) (2, the 4-3,5-dimethylphenyl) selenide-1H-1,2,4-triazole synthetic
With 2, the 4-xylidine is a raw material, obtains yellow solid according to the method for (4) in the example 1.Productive rate 77%, M.p.177-179 ℃
(2) 1-(N, N '-diethylamino) formyl radical-3-(1H-1,2,4-triazole) selenonyl-(2, the 4-dimethyl benzene) is synthetic
With (2, the 4-3,5-dimethylphenyl) selenide-1H-1,2, the 4-triazole is a raw material, the method that reaches (6) according to (5) in the example 1 obtains white solid.Productive rate 82%, M.p.137-139 ℃.MS (ESI) m/z:407 (M+Na
+), ultimate analysis: theoretical value C 47.00% H 5.26% N 14.62%, measured value C 47.02% H 5.25% N 14.58%.
Embodiment 16
1-(N, N '-diethylamino) formyl radical-3-(1H-1,2,4-triazole) selenonyl-(4-oil of mirbane)
(1) (4-nitrophenyl) selenide-1H-1,2,4-triazole synthetic:
With the 4-N-methyl-p-nitroaniline is raw material, obtains yellow solid according to the method for (4) in the example 1.Productive rate 52%, M.p.150-151 ℃.
(2) 1-(N, N '-diethylamino) formyl radical-3-(1H-1,2,4-triazole) selenonyl-(4-oil of mirbane) is synthetic:
With (2, the 4-3,5-dimethylphenyl) selenide-1H-1,2, the 4-triazole is a raw material, the method that reaches (6) according to (5) in the example 1 obtains white solid.Productive rate 82%, M.p.151-152 ℃.MS (ESI) m/z:424 (M+Na
+), ultimate analysis: theoretical value C 39.01% H 3.78% N 17.50%, measured value C 39.06% H 3.78% N 17.54%.
Embodiment 17
1-(N, N '-diethylamino) formyl radical-3-(1H-1,2,4-triazole) selenonyl-(2,4 difluorobenzene)
(1) (2,4 difluorobenzene base) selenide-1H-1,2,4-triazole synthetic:
With 2,4 difluorobenzene amine is raw material, obtains yellow solid according to the method for (4) in the example 1.Productive rate 79%, M.p.131-132 ℃
(2) 1-(N, N '-diethylamino) formyl radical-3-(1H-1,2,4-triazole) selenonyl-(2,4 difluorobenzene) is synthetic:
With (2,4 difluorobenzene base) selenide-1H-1,2, the 4-triazole is a raw material, the method that reaches (6) according to (5) in the example 1 obtains white solid.Productive rate 69%, M.p.160-161 ℃.MS (ESI) m/z:415 (M+Na
+), ultimate analysis: theoretical value C 39.91% H 3.61% F 9.71% N 14.32%, measured value C 39.97% H 3.63% F9.70% N 14.40%.
Embodiment 18
1-(N, N '-diethylamino) formyl radical-3-(1H-1,2,4-triazole) selenonyl-(3-chloro-4-trifluoromethylbenzene)
(1) (3-chloro-4-trifluoromethyl) selenide-1H-1,2,4-triazole synthetic
3-chloro-4-5-trifluoromethylaniline is a raw material, obtains yellow solid according to the method for (4) in the example 1.Productive rate 79%, M.p.131-132 ℃
(2) 1-(N, N '-diethylamino) formyl radical-3-(1H-1,2,4-triazole) selenonyl-(3-chloro-4-trifluoromethylbenzene) is synthetic:
With (3-chloro-4-trifluoromethyl) selenide-1H-1,2, the 4-triazole is a raw material, the method that reaches (6) according to (5) in the example 1 obtains white solid.Productive rate 69%, M.p.160-161 ℃.MS (ESI) m/z:4481 (M+Na
+), ultimate analysis: theoretical value C 36.74% H 3.08% Cl 7.75% F 12.45% N 12.24%, measured value C36.80% H 3.07% Cl 7.75% F 12.47% N 12.20%.
Embodiment 19
1-(N, N '-diethylamino) formyl radical-3-(1H-1,2,4-triazole) selenonyl-(4-anisole)
(1) (4-p-methoxy-phenyl) selenide-1H-1,2,4-triazole synthetic:
With the 4-anisidine is raw material, obtains yellow solid according to the method for (4) in the example 1.Productive rate 58%, M.p.116-117 ℃.
(2) 1-(N, N '-diethylamino) formyl radical-3-(1H-1,2,4-triazole) selenonyl-(4-anisole) is synthetic:
With (4-p-methoxy-phenyl) selenide-1H-1,2, the 4-triazole is a raw material, the method that reaches (6) according to (5) in the example 1 obtains white solid.Productive rate 71%, M.p.112-113 ℃.MS (ESI) m/z:409 (M+Na
+), ultimate analysis: theoretical value C 43.64% H 4.71% N 14.54%, measured value C 43.61% H 4.73% N 14.58%.
Embodiment 20
1-(N, N '-dimethylamino) formyl radical-3-(1H-1,2,4-triazole) selenonyl-(3-chloro-4-trifluoromethylbenzene)
(1) (3-chloro-4-trifluoromethyl) selenide-1H-1,2,4-triazole synthetic:
With 3-chloro-4-5-trifluoromethylaniline is raw material, obtains yellow solid according to the method for (4) in the example 1.Productive rate 69%, M.p.117-119 ℃.
(2) 1-(N, N '-dimethylamino) formyl radical-3-(1H-1,2,4-triazole) selenonyl-(3-chloro-4-trifluoromethylbenzene) is synthetic:
With (3-chloro-4-trifluoromethyl) selenide-1H-1,2, the 4-triazole is a raw material, the method that reaches (6) according to (5) in the example 1 obtains white solid.Productive rate 52%, M.p.163-164 ℃.MS (ESI) m/z:453 (M+Na
+), ultimate analysis: theoretical value C 33.55% H 2.35% Cl 8.25% F 13.27% N 13.04%, measured value C33.51% H 2.36% Cl 8.23% F 13.30% N 13.01%.
Embodiment 21
The weeding activity test of compound of the present invention:
For test agent is serial target compound missible oil, is wheat, paddy rice, Semen Euphorbiae and barnyard grass grass etc. for the examination object.Test method is that little alms bowl method is done and broadcast back seedling pre-treatment, concrete experimentation is as follows: seeds such as wheat, paddy rice are puddled in the little alms bowl that pollution-free mountain forest soil is housed (Φ=8cm), all target compounds are handled with the solution of 100ppm, each concentration of treatment is carried out three repetitions, establishes blank simultaneously.Following cultivating method in the whole experiment manages.After 10-15 days, observe anti-division result.To cucumber and wheatland top cauline leaf and underground root weighing fresh weight, the calculational chemistry product are to the biological activity of wheat and paddy rice etc. with weighing method.Test-results is to represent that to the inhibiting rate of growths such as wheat concrete test result sees the following form
| Sequence number | ??R | ??A | ??n | ??R 1 | ??R 2 | Inhibiting rate % (100ppm) | |||
| Wheat | Semen Euphorbiae | Paddy rice | The barnyard grass grass | ||||||
| ????1 | 2,4, the 6-trimethylammonium | Phenyl | ??0 | Ethyl | Ethyl | ??0 | ??0 | ??0 | ???0 |
| ????2 | 2,4, the 6-trimethylammonium | Phenyl | ??0 | Methyl | Methyl | ??0 | ??0 | ??0 | ???0 |
| ????3 | 2,4, the 6-trimethylammonium | Phenyl | ??0 | Propyl group | Propyl group | ??0 | ??0 | ??0 | ???0 |
| ????4 | 2,4, the 6-trimethylammonium | Phenyl | ??0 | Butyl | Butyl | ??0 | ??0 | ??0 | ???0 |
| ????5 | 2,4, the 6-trimethylammonium | Phenyl | ??0 | Ethyl | Methyl | ??0 | ??0 | ??0 | ???0 |
| ????6 | 2,4, the 6-trimethylammonium | Phenyl | ??0 | Ethyl | Propyl group | ??0 | ??0 | ??0 | ???0 |
| ????7 | 2,4, the 6-trimethylammonium | Phenyl | ??0 | Ethyl | Butyl | ??0 | ??0 | ??0 | ???0 |
| ????8 | 2,4, the 6-trimethylammonium | Phenyl | ??0 | Methyl | Propyl group | ??0 | ??0 | ??0 | ???0 |
| ????9 | 2,4, the 6-trimethylammonium | Phenyl | ??0 | Methyl | Butyl | ??0 | ??0 | ??0 | ???0 |
| ????10 | 2,4, the 6-trimethylammonium | Phenyl | ??0 | Propyl group | Butyl | ??0 | ??0 | ??0 | ???0 |
| ????11 | 2,4, the 6-trimethylammonium | Phenyl | ??1 | Ethyl | Ethyl | ??5 | ??20 | ??0 | ???15 |
| ????12 | 2,4, the 6-trimethylammonium | Phenyl | ??1 | Methyl | Methyl | ??3 | ??18 | ??0 | ???10 |
| ????13 | 2,4, the 6-trimethylammonium | Phenyl | ??1 | Propyl group | Propyl group | ??3 | ??9 | ??0 | ???9 |
| ????14 | 2,4, the 6-trimethylammonium | Phenyl | ??1 | Butyl | Butyl | ??0 | ??5 | ??0 | ???4 |
| ????15 | 2,4, the 6-trimethylammonium | Phenyl | ??1 | Ethyl | Methyl | ??3 | ??6 | ??0 | ???8 |
| ????16 | 2,4, the 6-trimethylammonium | Phenyl | ??1 | Ethyl | Propyl group | ??3 | ??12 | ??0 | ???10 |
| ????17 | 2,4, the 6-trimethylammonium | Phenyl | ??1 | Ethyl | Butyl | ??0 | ??0 | ??0 | ???0 |
| ????18 | 2,4, the 6-trimethylammonium | Phenyl | ??1 | Methyl | Propyl group | ??0 | ??0 | ??0 | ???0 |
| ????19 | 2,4, the 6-trimethylammonium | Phenyl | ??1 | Methyl | Butyl | ??0 | ??0 | ??0 | ???0 |
| ????20 | 2,4, the 6-trimethylammonium | Phenyl | ??1 | Propyl group | Butyl | ??0 | ??0 | ??0 | ???0 |
| ????21 | 2,4, the 6-trimethylammonium | Phenyl | ??2 | Ethyl | Ethyl | ??15 | ??100 | ??0 | ???100 |
| ????22 | 2,4, the 6-trimethylammonium | Phenyl | ??2 | Methyl | Methyl | ??3 | ??78 | ??0 | ???75 |
| ????23 | 2,4, the 6-trimethylammonium | Phenyl | ??2 | Propyl group | Propyl group | ??5 | ??80 | ??0 | ???78 |
| ????24 | 2,4, the 6-trimethylammonium | Phenyl | ??2 | Butyl | Butyl | ??0 | ??38 | ??0 | ???35 |
| Sequence number | ??R | A | ??n | ??R 1 | R 2 | Inhibiting rate % (100ppm) | |||
| Wheat | Semen Euphorbiae | Paddy rice | The barnyard grass grass | ||||||
| ????25 | 2,4, the 6-trimethylammonium | Phenyl | ??2 | Ethyl | Methyl | 6 | ??88 | ??0 | ???88 |
| ????26 | 2,4, the 6-trimethylammonium | Phenyl | ??2 | Ethyl | Propyl group | 6 | ??91 | ??0 | ???89 |
| ????27 | 2,4, the 6-trimethylammonium | Phenyl | ??2 | Ethyl | Butyl | 0 | ??34 | ??0 | ???36 |
| ????28 | 2,4, the 6-trimethylammonium | Phenyl | ??2 | Methyl | Propyl group | 0 | ??25 | ??0 | ???20 |
| ????29 | 2,4, the 6-trimethylammonium | Phenyl | ??2 | Methyl | Butyl | 0 | ??0 | ??0 | ???0 |
| ????30 | 2,4, the 6-trimethylammonium | Phenyl | ??2 | Propyl group | Butyl | 0 | ??0 | ??0 | ???0 |
| ????31 | 2,4, the 6-trimethylammonium | Phenyl | ??2 | Ethyl | Ethyl | 15 | ??100 | ??0 | ???100 |
| ????32 | 2,4, the 6-trimethylammonium | Phenyl | ??3 | Ethyl | Ethyl | 15 | ??100 | ??0 | ???100 |
| ????33 | 2,4, the 6-trimethylammonium | Phenyl | ??3 | Methyl | Methyl | 10 | ??87 | ??0 | ???85 |
| ????34 | 2,4, the 6-trimethylammonium | Phenyl | ??3 | Propyl group | Propyl group | 0 | ??96 | ??0 | ???90 |
| ????35 | 2,4, the 6-trimethylammonium | Phenyl | ??3 | Butyl | Butyl | 0 | ??58 | ??0 | ???55 |
| ????36 | 2,4, the 6-trimethylammonium | Phenyl | ??3 | Ethyl | Methyl | 0 | ??71 | ??0 | ???60 |
| ????37 | 2,4, the 6-trimethylammonium | Phenyl | ??3 | Ethyl | Propyl group | 0 | ??59 | ??0 | ???60 |
| ????38 | 2,4, the 6-trimethylammonium | Phenyl | ??3 | Ethyl | Butyl | 0 | ??37 | ??0 | ???35 |
| ????39 | 2,4, the 6-trimethylammonium | Phenyl | ??3 | Methyl | Propyl group | 0 | ??29 | ??0 | ???30 |
| ????40 | 2,4, the 6-trimethylammonium | Phenyl | ??3 | Methyl | Butyl | 0 | ??33 | ??0 | ???25 |
| ????41 | 2,4, the 6-trimethylammonium | Phenyl | ??3 | Propyl group | Butyl | 0 | ??15 | ??0 | ???10 |
| ????42 | The 3-methyl | The 2-pyridyl | ??0 | Ethyl | Ethyl | 0 | ??0 | ??0 | ???0 |
| ????43 | The 3-methyl | The 2-pyridyl | ??0 | Methyl | Methyl | 0 | ??0 | ??0 | ???0 |
| ????44 | The 3-methyl | The 2-pyridyl | ??0 | Propyl group | Propyl group | 0 | ??0 | ??0 | ???0 |
| ????45 | The 3-methyl | The 2-pyridyl | ??0 | Butyl | Butyl | 0 | ??0 | ??0 | ???0 |
| ????46 | The 3-methyl | The 2-pyridyl | ??0 | Ethyl | Methyl | 0 | ??0 | ??0 | ???0 |
| ????47 | The 3-methyl | The 2-pyridyl | ??0 | Ethyl | Propyl group | 0 | ??0 | ??0 | ???0 |
| ????48 | The 3-methyl | The 2-pyridyl | ??0 | Ethyl | Butyl | 0 | ??0 | ??0 | ???0 |
| ????49 | The 3-methyl | The 2-pyridyl | ??0 | Methyl | Propyl group | 0 | ??0 | ??0 | ???0 |
| ????50 | The 3-methyl | The 2-pyridyl | ??0 | Methyl | Butyl | 0 | ??0 | ??0 | ???0 |
| ????51 | The 3-methyl | The 2-pyridyl | ??0 | Propyl group | Butyl | 0 | ??0 | ??0 | ???0 |
| ????52 | The 3-methyl | The 2-pyridyl | ??1 | Ethyl | Ethyl | 0 | ??11 | ??0 | ???8 |
| ????53 | The 3-methyl | The 2-pyridyl | ??1 | Methyl | Methyl | 0 | ??0 | ??0 | ???0 |
| ????54 | The 3-methyl | The 2-pyridyl | ??1 | Propyl group | Propyl group | 0 | ??0 | ??0 | ???0 |
| ????55 | The 3-methyl | The 2-pyridyl | ??1 | Butyl | Butyl | 0 | ??0 | ??0 | ???0 |
| ????56 | The 3-methyl | The 2-pyridyl | ??1 | Ethyl | Methyl | 0 | ??0 | ??0 | ???0 |
| ????57 | The 3-methyl | The 2-pyridyl | ??1 | Ethyl | Propyl group | 0 | ??0 | ??0 | ???0 |
| ????58 | The 3-methyl | The 2-pyridyl | ??1 | Ethyl | Butyl | 0 | ??0 | ??0 | ???0 |
| ????59 | The 3-methyl | The 2-pyridyl | ??1 | Methyl | Propyl group | 0 | ??0 | ??0 | ???0 |
| ????60 | The 3-methyl | The 2-pyridyl | ??1 | Methyl | Butyl | 0 | ??0 | ??0 | ???0 |
| ????61 | The 3-methyl | The 2-pyridyl | ??1 | Propyl group | Butyl | 0 | ??0 | ??0 | ???0 |
| ????62 | The 3-methyl | The 2-pyridyl | ??2 | Ethyl | Ethyl | 10 | ??100 | ??0 | ???100 |
| ????63 | The 3-methyl | The 2-pyridyl | ??2 | Methyl | Methyl | 5 | ??91 | ??0 | ???85 |
| Sequence number | ????R | ??A | ??n | R 1 | R 2 | Inhibiting rate % (100ppm) | |||
| Wheat | Semen Euphorbiae | Paddy rice | The barnyard grass grass | ||||||
| ????64 | The 3-methyl | The 2-pyridyl | ??2 | Propyl group | Propyl group | ??5 | ??93 | ??0 | ??90 |
| ????65 | The 3-methyl | The 2-pyridyl | ??2 | Butyl | Butyl | ??0 | ??58 | ??0 | ??55 |
| ????66 | The 3-methyl | The 2-pyridyl | ??2 | Ethyl | Methyl | ??6 | ??93 | ??0 | ??90 |
| ????67 | The 3-methyl | The 2-pyridyl | ??2 | Ethyl | Propyl group | ??7 | ??88 | ??0 | ??85 |
| ????68 | The 3-methyl | The 2-pyridyl | ??2 | Ethyl | Butyl | ??3 | ??39 | ??0 | ??40 |
| ????69 | The 3-methyl | The 2-pyridyl | ??2 | Methyl | Propyl group | ??0 | ??42 | ??0 | ??43 |
| ????70 | The 3-methyl | The 2-pyridyl | ??2 | Methyl | Butyl | ??0 | ??38 | ??0 | ??30 |
| ????71 | The 3-methyl | The 2-pyridyl | ??2 | Propyl group | Butyl | ??0 | ??27 | ??0 | ??25 |
| ????72 | The 3-methyl | The 2-pyridyl | ??3 | Ethyl | Ethyl | ??17 | ??100 | ??0 | ??100 |
| ????73 | The 3-methyl | The 2-pyridyl | ??3 | Methyl | Methyl | ??7 | ??82 | ??0 | ??80 |
| ????74 | The 3-methyl | The 2-pyridyl | ??3 | Propyl group | Propyl group | ??9 | ??81 | ??0 | ??78 |
| ????75 | The 3-methyl | The 2-pyridyl | ??3 | Butyl | Butyl | ??0 | ??62 | ??0 | ??60 |
| ????76 | The 3-methyl | The 2-pyridyl | ??3 | Ethyl | Methyl | ??5 | ??78 | ??0 | ??75 |
| ????77 | The 3-methyl | The 2-pyridyl | ??3 | Ethyl | Propyl group | ??7 | ??74 | ??0 | ??73 |
| ????78 | The 3-methyl | The 2-pyridyl | ??3 | Ethyl | Butyl | ??0 | ??50 | ??0 | ??45 |
| ????79 | The 3-methyl | The 2-pyridyl | ??3 | Methyl | Propyl group | ??0 | ??49 | ??0 | ??50 |
| ????80 | The 3-methyl | The 2-pyridyl | ??3 | Methyl | Butyl | ??0 | ??46 | ??0 | ??39 |
| ????81 | The 3-methyl | The 2-pyridyl | ??3 | Propyl group | Butyl | ??0 | ??31 | ??0 | ??20 |
| ????82 | 2, the 6-dimethyl | Phenyl | ??0 | Ethyl | Ethyl | ??0 | ??0 | ??0 | ??0 |
| ????83 | 2, the 6-dimethyl | Phenyl | ??0 | Methyl | Methyl | ??0 | ??0 | ??0 | ??0 |
| ????84 | 2, the 6-dimethyl | Phenyl | ??0 | Propyl group | Propyl group | ??0 | ??0 | ??0 | ??0 |
| ????85 | 2, the 6-dimethyl | Phenyl | ??0 | Butyl | Butyl | ??0 | ??0 | ??0 | ??0 |
| ????86 | 2, the 6-dimethyl | Phenyl | ??0 | Ethyl | Methyl | ??0 | ??0 | ??0 | ??0 |
| ????87 | 2, the 6-dimethyl | Phenyl | ??0 | Ethyl | Propyl group | ??0 | ??0 | ??0 | ??0 |
| ????88 | 2, the 6-dimethyl | Phenyl | ??0 | Ethyl | Butyl | ??0 | ??0 | ??0 | ??0 |
| ????89 | 2, the 6-dimethyl | Phenyl | ??0 | Methyl | Propyl group | ??0 | ??0 | ??0 | ??0 |
| ????90 | 2, the 6-dimethyl | Phenyl | ??0 | Methyl | Butyl | ??0 | ??0 | ??0 | ??0 |
| ????91 | 2, the 6-dimethyl | Phenyl | ??0 | Propyl group | Butyl | ??0 | ??0 | ??0 | ??0 |
| ????92 | 2, the 6-dimethyl | Phenyl | ??1 | Ethyl | Ethyl | ??0 | ??15 | ??0 | ??12 |
| ????93 | 2, the 6-dimethyl | Phenyl | ??1 | Methyl | Methyl | ??0 | ??9 | ??0 | ??8 |
| ????94 | 2, the 6-dimethyl | Phenyl | ??1 | Propyl group | Propyl group | ??0 | ??8 | ??0 | ??9 |
| ????95 | 2, the 6-dimethyl | Phenyl | ??1 | Butyl | Butyl | ??0 | ??0 | ??0 | ??0 |
| ????96 | 2, the 6-dimethyl | Phenyl | ??1 | Ethyl | Methyl | ??0 | ??0 | ??0 | ??0 |
| ????97 | 2, the 6-dimethyl | Phenyl | ??1 | Ethyl | Propyl group | ??0 | ??0 | ??0 | ??0 |
| ????98 | 2, the 6-dimethyl | Phenyl | ??1 | Ethyl | Butyl | ??0 | ??0 | ??0 | ??0 |
| ????99 | 2, the 6-dimethyl | Phenyl | ??1 | Methyl | Propyl group | ??0 | ??0 | ??0 | ??0 |
| ????100 | 2, the 6-dimethyl | Phenyl | ??1 | Methyl | Butyl | ??0 | ??0 | ??0 | ??0 |
| ????101 | 2, the 6-dimethyl | Phenyl | ??1 | Propyl group | Butyl | ??0 | ??0 | ??0 | ??0 |
| ????102 | 2, the 6-dimethyl | Phenyl | ??2 | Ethyl | Ethyl | ??9 | ??100 | ??0 | ??100 |
| Sequence number | ????R | ??A | ??n | ??R 1 | ??R 2 | Inhibiting rate % (100ppm) | |||
| Wheat | Semen Euphorbiae | Paddy rice | The barnyard grass grass | ||||||
| ??103 | 2, the 6-dimethyl | Phenyl | ??2 | Methyl | Methyl | ??4 | ??77 | ??0 | ????75 |
| ??104 | 2, the 6-dimethyl | Phenyl | ??2 | Propyl group | Propyl group | ??5 | ??82 | ??0 | ????80 |
| ??105 | 2, the 6-dimethyl | Phenyl | ??2 | Butyl | Butyl | ??0 | ??41 | ??0 | ????35 |
| ??106 | 2, the 6-dimethyl | Phenyl | ??2 | Ethyl | Methyl | ??0 | ??42 | ??0 | ????40 |
| ??107 | 2, the 6-dimethyl | Phenyl | ??2 | Ethyl | Propyl group | ??3 | ??80 | ??0 | ????47 |
| ??108 | 2, the 6-dimethyl | Phenyl | ??2 | Ethyl | Butyl | ??0 | ??38 | ??0 | ????34 |
| ??109 | 2, the 6-dimethyl | Phenyl | ??2 | Methyl | Propyl group | ??0 | ??21 | ??0 | ????20 |
| ??110 | 2, the 6-dimethyl | Phenyl | ??2 | Methyl | Butyl | ??0 | ??15 | ??0 | ????10 |
| ??111 | 2, the 6-dimethyl | Phenyl | ??2 | Propyl group | Butyl | ??0 | ??0 | ??0 | ????0 |
| ??112 | 2, the 6-dimethyl | Phenyl | ??3 | Ethyl | Ethyl | ??13 | ??100 | ??0 | ????100 |
| ??113 | 2, the 6-dimethyl | Phenyl | ??3 | Methyl | Methyl | ??5 | ??75 | ??0 | ????70 |
| ??114 | 2, the 6-dimethyl | Phenyl | ??3 | Propyl group | Propyl group | ??6 | ??81 | ??0 | ????77 |
| ??115 | 2, the 6-dimethyl | Phenyl | ??3 | Butyl | Butyl | ??0 | ??24 | ??0 | ????21 |
| ??116 | 2, the 6-dimethyl | Phenyl | ??3 | Ethyl | Methyl | ??2 | ??61 | ??0 | ????59 |
| ??117 | 2, the 6-dimethyl | Phenyl | ??3 | Ethyl | Propyl group | ??2 | ??63 | ??0 | ????60 |
| ??118 | 2, the 6-dimethyl | Phenyl | ??3 | Ethyl | Butyl | ??0 | ??38 | ?0 | ????25 |
| ??119 | 2, the 6-dimethyl | Phenyl | ??3 | Methyl | Propyl group | ??0 | ??20 | ??0 | ????10 |
| ??120 | 2, the 6-dimethyl | Phenyl | ??3 | Methyl | Butyl | ??0 | ??0 | ??0 | ????0 |
| ??121 | 2, the 6-dimethyl | Phenyl | ??3 | Propyl group | Butyl | ??0 | ??0 | ??0 | ????0 |
| ??122 | 2, the 4-dimethyl | Phenyl | ??0 | Ethyl | Ethyl | ??0 | ??0 | ??0 | ????0 |
| ??123 | 2, the 4-dimethyl | Phenyl | ??0 | Methyl | Methyl | ??0 | ??0 | ??0 | ????0 |
| ??124 | 2, the 4-dimethyl | Phenyl | ??0 | Propyl group | Propyl group | ??0 | ??0 | ??0 | ????0 |
| ??125 | 2, the 4-dimethyl | Phenyl | ??0 | Butyl | Butyl | ??0 | ??0 | ??0 | ????0 |
| ??126 | 2, the 4-dimethyl | Phenyl | ??1 | Ethyl | Ethyl | ??0 | ??14 | ??0 | ????10 |
| ??127 | 2, the 4-dimethyl | Phenyl | ??1 | Methyl | Methyl | ??0 | ??0 | ??0 | ????0 |
| ??128 | 2, the 4-dimethyl | Phenyl | ??1 | Propyl group | Propyl group | ??0 | ??0 | ??0 | ????0 |
| ??129 | 2, the 4-dimethyl | Phenyl | ??1 | Butyl | Butyl | ??0 | ??0 | ??0 | ????0 |
| ??130 | 2, the 4-dimethyl | Phenyl | ??2 | Ethyl | Ethyl | ??3 | ??100 | ??0 | ????98 |
| ??131 | 2, the 4-dimethyl | Phenyl | ??2 | Methyl | Methyl | ??0 | ??71 | ??0 | ????66 |
| ??132 | 2, the 4-dimethyl | Phenyl | ??2 | Propyl group | Propyl group | ??0 | ??68 | ??0 | ????58 |
| ??133 | 2, the 4-dimethyl | Phenyl | ??2 | Butyl | Butyl | ??0 | ??21 | ??0 | ????14 |
| ??134 | 2, the 4-dimethyl | Phenyl | ??3 | Ethyl | Ethyl | ??7 | ??100 | ??0 | ????100 |
| ??135 | 2, the 4-dimethyl | Phenyl | ??3 | Methyl | Methyl | ??0 | ??82 | ??0 | ????79 |
| ??136 | 2, the 4-dimethyl | Phenyl | ??3 | Propyl group | Propyl group | ??0 | ??40 | ??0 | ????38 |
| ??137 | 2, the 4-dimethyl | Phenyl | ??3 | Butyl | Butyl | ??0 | ??46 | ??0 | ????42 |
| ??138 | The 4-nitro | Phenyl | ??0 | Ethyl | Ethyl | ??0 | ??0 | ??0 | ????0 |
| ??139 | The 4-nitro | Phenyl | ??0 | Methyl | Methyl | ??0 | ??0 | ??0 | ????0 |
| ??140 | The 4-nitro | Phenyl | ??0 | Propyl group | Propyl group | ??0 | ??0 | ??0 | ????0 |
| ??141 | The 4-nitro | Phenyl | ??0 | Butyl | Butyl | ??0 | ??0 | ??0 | ????0 |
| Sequence number | ????R | ??A | ??n | ??R 1 | ??R 2 | Inhibiting rate % (100ppm) | |||
| Wheat | Semen Euphorbiae | Paddy rice | The barnyard grass grass | ||||||
| ????142 | The 4-nitro | Phenyl | ??1 | Ethyl | Ethyl | ??0 | ??0 | ??0 | ????0 |
| ????143 | The 4-nitro | Phenyl | ??1 | Methyl | Methyl | ??0 | ??0 | ??0 | ????0 |
| ????144 | The 4-nitro | Phenyl | ??1 | Propyl group | Propyl group | ??0 | ??0 | ??0 | ????0 |
| ????145 | The 4-nitro | Phenyl | ??1 | Butyl | Butyl | ??0 | ??0 | ??0 | ????0 |
| ????146 | The 4-nitro | Phenyl | ??2 | Ethyl | Ethyl | ??0 | ??91 | ??0 | ????85 |
| ????147 | The 4-nitro | Phenyl | ??2 | Methyl | Methyl | ??0 | ??42 | ??0 | ????35 |
| ????148 | The 4-nitro | Phenyl | ??2 | Propyl group | Propyl group | ??0 | ??44 | ??0 | ????36 |
| ????149 | The 4-nitro | Phenyl | ??2 | Butyl | Butyl | ??0 | ??0 | ??0 | ????0 |
| ????150 | The 4-nitro | Phenyl | ??3 | Ethyl | Ethyl | ??4 | ??100 | ??0 | ????94 |
| ????151 | The 4-nitro | Phenyl | ??3 | Methyl | Methyl | ??0 | ??54 | ??0 | ????48 |
| ????152 | The 4-nitro | Phenyl | ??3 | Propyl group | Propyl group | ??0 | ??50 | ??0 | ????45 |
| ????153 | The 4-nitro | Phenyl | ??3 | Butyl | Butyl | ??0 | ??0 | ??0 | ????0 |
| ????154 | 2, the 4-difluoro | Phenyl | ??0 | Ethyl | Ethyl | ??0 | ??0 | ??0 | ????0 |
| ????155 | 2, the 4-difluoro | Phenyl | ??0 | Methyl | Methyl | ??0 | ??0 | ??0 | ????0 |
| ????156 | 2, the 4-difluoro | Phenyl | ??0 | Propyl group | Propyl group | ??0 | ??0 | ??0 | ????0 |
| ????157 | 2, the 4-difluoro | Phenyl | ??0 | Butyl | Butyl | ??0 | ??0 | ??0 | ????0 |
| ????158 | 2, the 4-difluoro | Phenyl | ??1 | Ethyl | Ethyl | ??0 | ??0 | ??0 | ????0 |
| ????159 | 2, the 4-difluoro | Phenyl | ??1 | Methyl | Methyl | ??0 | ??0 | ??0 | ????0 |
| ????160 | 2, the 4-difluoro | Phenyl | ??1 | Propyl group | Propyl group | ??0 | ??0 | ??0 | ????0 |
| ????161 | 2, the 4-difluoro | Phenyl | ??1 | Butyl | Butyl | ??0 | ??0 | ??0 | ????0 |
| ????162 | 2, the 4-difluoro | Phenyl | ??2 | Ethyl | Ethyl | ??3 | ??62 | ??0 | ????56 |
| ????163 | 2, the 4-difluoro | Phenyl | ??2 | Methyl | Methyl | ??0 | ??21 | ??0 | ????17 |
| ????164 | 2, the 4-difluoro | Phenyl | ??2 | Propyl group | Propyl group | ??0 | ??19 | ??0 | ????12 |
| ????165 | 2, the 4-difluoro | Phenyl | ??2 | Butyl | Butyl | ??0 | ??0 | ??0 | ????0 |
| ????166 | 2, the 4-difluoro | Phenyl | ??3 | Ethyl | Ethyl | ??3 | ??95 | ??0 | ????87 |
| ????167 | 2, the 4-difluoro | Phenyl | ??3 | Methyl | Methyl | ??0 | ??41 | ??0 | ????33 |
| ????168 | 2, the 4-difluoro | Phenyl | ??3 | Propyl group | Propyl group | ??0 | ??43 | ??0 | ????31 |
| ????169 | 2, the 4-difluoro | Phenyl | ??3 | Butyl | Butyl | ??0 | ??11 | ??0 | ????8 |
| ????170 | 3-chloro-4-fluorine | Phenyl | ??0 | Ethyl | Ethyl | ??0 | ??0 | ??0 | ????0 |
| ????171 | 3-chloro-4-fluorine | Phenyl | ??0 | Methyl | Methyl | ??0 | ??0 | ??0 | ????0 |
| ????172 | 3-chloro-4-fluorine | Phenyl | ??0 | Propyl group | Propyl group | ??0 | ??0 | ??0 | ????0 |
| ????173 | 3-chloro-4-fluorine | Phenyl | ??0 | Butyl | Butyl | ??0 | ??0 | ??0 | ????0 |
| ????174 | 3-chloro-4-fluorine | Phenyl | ??1 | Ethyl | Ethyl | ??0 | ??0 | ??0 | ????0 |
| ????175 | 3-chloro-4-fluorine | Phenyl | ??1 | Methyl | Methyl | ??0 | ??0 | ??0 | ????0 |
| ????176 | 3-chloro-4-fluorine | Phenyl | ??1 | Propyl group | Propyl group | ??0 | ??0 | ??0 | ????0 |
| ????177 | 3-chloro-4-fluorine | Phenyl | ??1 | Butyl | Butyl | ??0 | ??0 | ??0 | ????0 |
| ????178 | 3-chloro-4-fluorine | Phenyl | ??2 | Ethyl | Ethyl | ??0 | ??65 | ??0 | ????60 |
| ????179 | 3-chloro-4-fluorine | Phenyl | ??2 | Methyl | Methyl | ??0 | ??21 | ??0 | ????12 |
| ????180 | 3-chloro-4-fluorine | Phenyl | ??2 | Propyl group | Propyl group | ??0 | ??20 | ??0 | ????18 |
| Sequence number | ????R | ???A | ??n | ??R 1 | ??R 2 | Inhibiting rate % (100ppm) | |||
| Wheat | Semen Euphorbiae | Paddy rice | The barnyard grass grass | ||||||
| ????181 | 3-chloro-4-fluorine | Phenyl | ??2 | Butyl | Butyl | ??0 | ??0 | ??0 | ??0 |
| ????182 | 3-chloro-4-fluorine | Phenyl | ??3 | Ethyl | Ethyl | ??0 | ??81 | ??0 | ??69 |
| ????183 | 3-chloro-4-fluorine | Phenyl | ??3 | Methyl | Methyl | ??0 | ??40 | ??0 | ??31 |
| ????184 | 3-chloro-4-fluorine | Phenyl | ??3 | Propyl group | Propyl group | ??0 | ??29 | ??0 | ??28 |
| ????185 | 3-chloro-4-fluorine | Phenyl | ??3 | Butyl | Butyl | ??0 | ??0 | ??0 | ????0 |
| ????186 | The 4-methoxyl group | Phenyl | ??0 | Ethyl | Ethyl | ??0 | ??0 | ??0 | ????0 |
| ????187 | The 4-methoxyl group | Phenyl | ??0 | Methyl | Methyl | ??0 | ??0 | ??0 | ????0 |
| ????188 | The 4-methoxyl group | Phenyl | ??0 | Propyl group | Propyl group | ??0 | ??0 | ??0 | ????0 |
| ????189 | The 4-methoxyl group | Phenyl | ??0 | Butyl | Butyl | ??0 | ??0 | ??0 | ????0 |
| ????190 | The 4-methoxyl group | Phenyl | ??1 | Ethyl | Ethyl | ??0 | ??0 | ??0 | ????0 |
| ????190 | The 4-methoxyl group | Phenyl | ??1 | Methyl | Methyl | ??0 | ??0 | ??0 | ????0 |
| ????191 | The 4-methoxyl group | Phenyl | ??1 | Propyl group | Propyl group | ??0 | ??0 | ??0 | ????0 |
| ????192 | The 4-methoxyl group | Phenyl | ??1 | Butyl | Butyl | ??0 | ??0 | ??0 | ????0 |
| ????193 | The 4-methoxyl group | Phenyl | ??2 | Ethyl | Ethyl | ??3 | ??100 | ??0 | ????95 |
| ????194 | The 4-methoxyl group | Phenyl | ??2 | Methyl | Methyl | ??0 | ??80 | ??0 | ????71 |
| ????195 | The 4-methoxyl group | Phenyl | ??2 | Propyl group | Propyl group | ??0 | ??7 | ??0 | ????63 |
| ????196 | The 4-methoxyl group | Phenyl | ??2 | Butyl | Butyl | ??0 | ??40 | ??0 | ????31 |
| ????197 | The 4-methoxyl group | Phenyl | ??3 | Ethyl | Ethyl | ??0 | ??100 | ??0 | ????97 |
| ????198 | The 4-methoxyl group | Phenyl | ??3 | Methyl | Methyl | ??0 | ??41 | ??0 | ????37 |
| ????199 | The 4-methoxyl group | Phenyl | ??3 | Propyl group | Propyl group | ??0 | ??45 | ??0 | ????34 |
| ????200 | The 4-methoxyl group | Phenyl | ??3 | Butyl | Butyl | ??0 | ??19 | ??0 | ????9 |
| ????201 | 3-chloro-4-trifluoromethyl | Phenyl | ??0 | Ethyl | Ethyl | ??0 | ??0 | ??0 | ????0 |
| ????202 | 3-chloro-4-trifluoromethyl | Phenyl | ??0 | Methyl | Methyl | ??0 | ??0 | ??0 | ????0 |
| ????203 | 3-chloro-4-trifluoromethyl | Phenyl | ??0 | Propyl group | Propyl group | ??0 | ??0 | ??0 | ????0 |
| ????204 | 3-chloro-4-trifluoromethyl | Phenyl | ??0 | Butyl | Butyl | ??0 | ??0 | ??0 | ????0 |
| ????205 | 3-chloro-4-trifluoromethyl | Phenyl | ??1 | Ethyl | Ethyl | ??0 | ??0 | ??0 | ????0 |
| ????206 | 3-chloro-4-trifluoromethyl | Phenyl | ??1 | Methyl | Methyl | ??0 | ??0 | ??0 | ????0 |
| ????207 | 3-chloro-4-trifluoromethyl | Phenyl | ??1 | Propyl group | Propyl group | ??0 | ??0 | ??0 | ????0 |
| ????208 | 3-chloro-4-trifluoromethyl | Phenyl | ??1 | Butyl | Butyl | ??0 | ??0 | ??0 | ????0 |
| ????209 | 3-chloro-4-trifluoromethyl | Phenyl | ??2 | Ethyl | Ethyl | ??0 | ??72 | ??0 | ????61 |
| ????210 | 3-chloro-4-trifluoromethyl | Phenyl | ??2 | Methyl | Methyl | ??0 | ??35 | ??0 | ????30 |
| ????211 | 3-chloro-4-trifluoromethyl | Phenyl | ??2 | Propyl group | Propyl group | ??0 | ??33 | ??0 | ????29 |
| ????212 | 3-chloro-4-trifluoromethyl | Phenyl | ??2 | Butyl | Butyl | ??0 | ??0 | ??0 | ????0 |
| ????213 | 3-chloro-4-trifluoromethyl | Phenyl | ??3 | Ethyl | Ethyl | ??0 | ??68 | ??0 | ????60 |
| ????214 | 3-chloro-4-trifluoromethyl | Phenyl | ??3 | Methyl | Methyl | ??0 | ??35 | ??0 | ????24 |
| ????215 | 3-chloro-4-trifluoromethyl | Phenyl | ??3 | Propyl group | Propyl group | ??0 | ??30 | ??0 | ????25 |
| ????216 | 3-chloro-4-trifluoromethyl | Phenyl | ??3 | Butyl | Butyl | ??0 | ??0 | ??0 | ????0 |
| ????217 | 1-methyl-3-ethyl | Pyrazoles | ??0 | Ethyl | Ethyl | ??0 | ??0 | ??0 | ????0 |
| ????218 | 1-methyl-3-ethyl | Pyrazoles | ??0 | Methyl | Methyl | ??0 | ??0 | ??0 | ????0 |
| Sequence number | ??R | ??A | ??n | ??R 1 | ??R 2 | Inhibiting rate % (100ppm) | |||
| Wheat | Semen Euphorbiae | Paddy rice | The barnyard grass grass | ||||||
| ????219 | 1-methyl-3-ethyl | Pyrazoles | ??0 | Propyl group | Propyl group | ??0 | ??0 | ??0 | ???0 |
| ????220 | 1-methyl-3-ethyl | Pyrazoles | ??0 | Butyl | Butyl | ??0 | ??0 | ??0 | ???0 |
| ????221 | 1-methyl-3-ethyl | Pyrazoles | ??1 | Ethyl | Ethyl | ??0 | ??0 | ??0 | ???0 |
| ????222 | 1-methyl-3-ethyl | Pyrazoles | ??1 | Methyl | Methyl | ??0 | ??0 | ??0 | ???0 |
| ????223 | 1-methyl-3-ethyl | Pyrazoles | ??1 | Propyl group | Propyl group | ??0 | ??0 | ??0 | ???0 |
| ????224 | 1-methyl-3-ethyl | Pyrazoles | ??1 | Butyl | Butyl | ??0 | ??0 | ??0 | ???0 |
| ????225 | 1-methyl-3-ethyl | Pyrazoles | ??2 | Ethyl | Ethyl | ??0 | ??100 | ??0 | ???100 |
| ????226 | 1-methyl-3-ethyl | Pyrazoles | ??2 | Methyl | Methyl | ??0 | ??61 | ??0 | ???54 |
| ????227 | 1-methyl-3-ethyl | Pyrazoles | ??2 | Propyl group | Propyl group | ??0 | ??63 | ??0 | ???58 |
| ????228 | 1-methyl-3-ethyl | Pyrazoles | ??2 | Butyl | Butyl | ??0 | ??29 | ??0 | ???25 |
| ????229 | 1-methyl-3-ethyl | Pyrazoles | ??3 | Ethyl | Ethyl | ??0 | ??100 | ??0 | ???100 |
| ????230 | 1-methyl-3-ethyl | Pyrazoles | ??3 | Methyl | Methyl | ??0 | ??40 | ??0 | ???36 |
| ????231 | 1-methyl-3-ethyl | Pyrazoles | ??3 | Propyl group | Propyl group | ??0 | ??43 | ??0 | ???41 |
| ????232 | 1-methyl-3-ethyl | Pyrazoles | ??3 | Butyl | Butyl | ??0 | ??21 | ??0 | ???18 |
| ????233 | 1-methyl-3-(2-bromotrifluoromethane) | Pyrazoles | ??0 | Ethyl | Ethyl | ??0 | ??0 | ??0 | ???0 |
| ????234 | 1-methyl-3-(2-bromotrifluoromethane) | Pyrazoles | ??0 | Methyl | Methyl | ??0 | ??0 | ??0 | ???0 |
| ????235 | 1-methyl-3-(2-bromotrifluoromethane) | Pyrazoles | ??0 | Propyl group | Propyl group | ??0 | ??0 | ??0 | ???0 |
| ????236 | 1-methyl-3-(2-bromotrifluoromethane) | Pyrazoles | ??0 | Butyl | Butyl | ??0 | ??0 | ??0 | ???0 |
| ????237 | 1-methyl-3-(2-bromotrifluoromethane) | Pyrazoles | ??1 | Ethyl | Ethyl | ??0 | ??0 | ??0 | ???0 |
| ????238 | 1-methyl-3-(2-bromotrifluoromethane) | Pyrazoles | ??1 | Methyl | Methyl | ??0 | ??0 | ??0 | ???0 |
| ????239 | 1-methyl-3-(2-bromotrifluoromethane) | Pyrazoles | ??1 | Propyl group | Propyl group | ??0 | ??0 | ??0 | ???0 |
| ????240 | 1-methyl-3-(2-bromotrifluoromethane) | Pyrazoles | ??1 | Butyl | Butyl | ??0 | ??0 | ??0 | ???0 |
| ????241 | 1-methyl-3-(2-bromotrifluoromethane) | Pyrazoles | ??2 | Ethyl | Ethyl | ??0 | ??100 | ??0 | ???100 |
| ????242 | 1-methyl-3-(2-bromotrifluoromethane) | Pyrazoles | ??2 | Methyl | Methyl | ??0 | ??51 | ??0 | ???44 |
| ????243 | 1-methyl-3-(2-bromotrifluoromethane) | Pyrazoles | ??2 | Propyl group | Propyl group | ??0 | ??40 | ??0 | ???37 |
| ????244 | 1-methyl-3-(2-bromotrifluoromethane) | Pyrazoles | ??2 | Butyl | Butyl | ??0 | ??21 | ??0 | ???12 |
| ????245 | 1-methyl-3-(2-bromotrifluoromethane) | Pyrazoles | ??3 | Ethyl | Ethyl | ??0 | ??100 | ??0 | ???100 |
| ????246 | 1-methyl-3-(2-bromotrifluoromethane) | Pyrazoles | ??3 | Methyl | Methyl | ??0 | ??70 | ??0 | ???61 |
| ????257 | 1-methyl-3-(2-bromotrifluoromethane) | Pyrazoles | ??3 | Propyl group | Propyl group | ??0 | ??60 | ??0 | ???58 |
| ????248 | 1-methyl-3-(2-bromotrifluoromethane) | Pyrazoles | ??3 | Butyl | Butyl | ??0 | ??21 | ??0 | ???11 |
| ????248 | Hydrogen | Thiazole | ??0 | Ethyl | Ethyl | ??0 | ??0 | ??0 | ???0 |
| ????250 | Hydrogen | Thiazole | ??1 | Ethyl | Ethyl | ??0 | ??0 | ??0 | ???0 |
| ????251 | Hydrogen | Thiazole | ??2 | Ethyl | Ethyl | ??0 | ??63 | ??0 | ???51 |
| ????252 | Hydrogen | Thiazole | ??3 | Ethyl | Ethyl | ??0 | ??75 | ??0 | ???66 |
| ????253 | Hydrogen | The pyrroles | ??0 | Ethyl | Ethyl | ??0 | ??0 | ??0 | ???0 |
| ????254 | Hydrogen | The pyrroles | ??1 | Ethyl | Ethyl | ??0 | ??0 | ??0 | ???0 |
| ????255 | Hydrogen | The pyrroles | ??2 | Ethyl | Ethyl | ??0 | ??41 | ??0 | ???30 |
| ????256 | Hydrogen | The pyrroles | ??3 | Ethyl | Ethyl | ??0 | ??58 | ??0 | ???49 |
Claims (14)
1, a kind of selenium triazolylamide compounds that contains, it has following structure:
In the formula: R
1, R
2Be C
1～C
8Alkyl;
On behalf of five yuan or hexavalent, A contain 1～3 heteroatomic heterocycle or aromatic ring;
R represents A substitution in ring base, is hydrogen, halogen, alkyl, nitro, haloalkyl and/or alkoxyl group;
N=0,1,2 or 3.
2, compound as claimed in claim 1 is characterized in that, n=0 wherein, 1 or 2.
3, compound as claimed in claim 2 is characterized in that, wherein A is pyrazoles, pyridine, thiazole, pyrroles or benzene.
4, compound as claimed in claim 3 is characterized in that, wherein R
1, R
2Be C
1～C
3Alkyl.
5, compound as claimed in claim 4 is characterized in that, wherein A is a benzene.
6, compound as claimed in claim 5 is characterized in that, wherein R represents 2-, 2-, 6-or 2-, 4-, the C that the 6-position replaces
1～C
4Alkyl.
7, compound as claimed in claim 1 is characterized in that, wherein n=3.
8, compound as claimed in claim 7 is characterized in that, wherein A is pyrazoles, pyridine, thiazole, pyrroles or benzene.
9, compound as claimed in claim 8 is characterized in that, wherein R
1, R
2Be C
1～C
3Alkyl.
10, compound as claimed in claim 9 is characterized in that, wherein A is a benzene.
11, compound as claimed in claim 10 is characterized in that, wherein R represents 2-, 2-, 6-or 2-, 4-, the C that the 6-position replaces
1～C
4Alkyl.
12, preparation is characterized in that as the method for any one compound in the claim 2～6 said preparation method comprises the steps:
1) to replace amine (R-A-NH
2) be starting raw material, at first make diazonium salt through diazotization, then diazonium salt and the selenides condensation that makes obtained fragrant triazole selenide;
2) carry out oxidation and can make triazole selenium (Asia) sulfone obtained fragrant triazole selenide by step 1), wherein said oxidation can be adopted in the following method for oxidation a kind of,
(1) in Glacial acetic acid, uses hydrogen peroxide oxidation;
(2) in Glacial acetic acid, carry out oxidation as catalyzer with sodium wolframate;
(3) in tetrahydrofuran (THF), ether, ketone, Glacial acetic acid with plumbic acetate for making catalyzer, use hydrogen peroxide oxidation;
(4) Oxone with Du Pont carries out oxidation as oxygenant;
3) with N, N dialkyl group formyl chloride respectively with the fragrant triazole selenide that makes by step 1), by step 2) the triazole selenone or the triazole selenoxide that make carry out condensation reaction, makes target product.
13, preparation is characterized in that as the method for any one compound in the claim 7～11 said preparation method's key step is as follows:
At first selenides is made triazolyl selenic acid through hydrogen peroxide oxidation, it is prepared into corresponding acyl chlorides then, the acyl chlorides and substituted phenol (R-A-OH) condensation that make are obtained selenium acyl triazole phenolic ester, and at last with gained selenium acyl triazole phenolic ester and N, the condensation of N dialkyl group formyl chloride gets target product.
14, can be used as the weedicide of farm crop as any one compound in the claim 1～11.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200310108478 CN1247548C (en) | 2003-11-06 | 2003-11-06 | Cesium triazoleamide compounds and their preparation and use |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200310108478 CN1247548C (en) | 2003-11-06 | 2003-11-06 | Cesium triazoleamide compounds and their preparation and use |
Publications (2)
| Publication Number | Publication Date |
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| CN1247548C CN1247548C (en) | 2006-03-29 |
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ID=34758604
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|---|---|---|---|
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| Country | Link |
|---|---|
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103086935A (en) * | 2011-10-28 | 2013-05-08 | 沈阳药科大学 | Diphenyl selenide, diphenyl selenoxide, diphenyl selenone compounds and uses thereof |
| CN104507925A (en) * | 2012-04-27 | 2015-04-08 | 巴斯夫欧洲公司 | Substituted N-(tetrazol-5-yl)- and N-(triazol-5-yl)pyridin-3-yl-carboxamide compounds and their use as herbicides |
-
2003
- 2003-11-06 CN CN 200310108478 patent/CN1247548C/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103086935A (en) * | 2011-10-28 | 2013-05-08 | 沈阳药科大学 | Diphenyl selenide, diphenyl selenoxide, diphenyl selenone compounds and uses thereof |
| CN103086935B (en) * | 2011-10-28 | 2015-05-20 | 沈阳药科大学 | Diphenyl selenide, diphenyl selenoxide, diphenyl selenone compounds and uses thereof |
| CN104507925A (en) * | 2012-04-27 | 2015-04-08 | 巴斯夫欧洲公司 | Substituted N-(tetrazol-5-yl)- and N-(triazol-5-yl)pyridin-3-yl-carboxamide compounds and their use as herbicides |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1247548C (en) | 2006-03-29 |
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Assignee: Qidong Dongyue Pharmacy Co., Ltd. Assignor: East China University of Science and Technology Contract fulfillment period: 2006.4.15 to 2011.4.14 contract change Contract record no.: 2008320000528 Denomination of invention: Cesium triazoleamide compounds and their preparation and use Granted publication date: 20060329 License type: Exclusive license Record date: 2008.10.6 |
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