CN102442969B - Butyne ether compound and application thereof - Google Patents

Butyne ether compound and application thereof Download PDF

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CN102442969B
CN102442969B CN201010502808.1A CN201010502808A CN102442969B CN 102442969 B CN102442969 B CN 102442969B CN 201010502808 A CN201010502808 A CN 201010502808A CN 102442969 B CN102442969 B CN 102442969B
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compound
general formula
trifluoromethyl
formula
butyne
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CN102442969A (en
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关爱莹
李斌
常秀辉
梁松军
宋玉泉
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Shenyang Sinochem Agrochemicals R&D Co Ltd
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Shenyang Research Institute of Chemical Industry Co Ltd
Sinochem Corp
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Abstract

The invention discloses a butyne ether compound and application thereof, and discloses a dichloropropylene compound with a novel structure which is shown as a general formula I in the description, wherein, Q is selected from Q1, Q2, Q3 shown in the desctiption; R1, R2, R3, R4, R5, R6, R7 and R8 can be the same or different, and are selected from H, fluorine, chlorine, bromine, iodine, CN, NO2, C1-C3 alkyls, C1-C3 halogenated alkyls, C1-C3 alkoxys, or C1-C3 halogenated alkoxys; X is selected from O, S, or N-R9; and R9 is selected from C1-C3 alkyls, allyl, or propargyl. Compound I shown as the general formula has excellent insecticidal activity and can be applied to preventing insect damage.

Description

A kind of Butyne ether compound and application thereof
Technical field
The invention belongs to field of pesticides.Relate to a kind of Butyne ether compound and application thereof.
Background technology
Due to sterilant in use for some time, insect can produce resistance to it, therefore, need constantly invention novel with compound and the composition of improved tool insecticidal activity.
Chinese patent application WO9604228 (A1) discloses the ether compound and the insecticidal activity thereof that contain ethylene linkage, wherein compound K C 1(compound 257 in patent), KC 2(compound 258 in patent) (structure is as follows) reaches more than 80% prodenia litura lethality rate under the concentration of 500ppm.
Figure BSA00000297418600011
In prior art, have no open for the bis ether compounds and the insecticidal activity thereof that contain acetylene bond in structure.
Summary of the invention
The object of the present invention is to provide a kind of novel structure, have the Butyne ether compound of insecticidal activity, it can be applicable to the control of insect pest in agricultural, forestry or health.
Technical scheme of the present invention is as follows:
The invention provides a kind of Butyne ether compound, as shown in general formula I:
Figure BSA00000297418600012
In formula:
Q is selected from Q as follows 1, Q 2or Q 3:
Wherein: R 1, R 2, R 3, R 4, R 5, R 6, R 7, R 8can be identical or different, be selected from respectively H, fluorine, chlorine, bromine, iodine, CN, NO 2, C 1-C 3alkyl, C 1-C 3haloalkyl, C 1-C 3alkoxyl group or C 1-C 3halogenated alkoxy;
X is selected from O, S or N-R 9; R 9be selected from C 1-C 3alkyl, allyl group or propargyl.
Butylene ether compound of the present invention can form respectively benzo five-membered (mixing) cyclobutyne ethers, substituted quinoxaline cyclobutyne ethers or substituted pyridines cyclobutyne ether compound according to the different choice of Q, and its structural formula is as follows respectively:
Figure BSA00000297418600021
In the present invention, more preferably compound is, in general formula I:
Q is selected from Q 1, Q 2or Q 3;
When Q is selected from Q 1time, R 1, R 2be selected from respectively H, fluorine, chlorine, bromine, NO 2, methyl or trifluoromethyl; X is selected from O, S or N-R 9;
When Q is selected from Q 2time, R 3, R 4be selected from respectively H, fluorine, chlorine, bromine, NO 2, methyl or trifluoromethyl, but R 3, R 4has one at least for H;
When Q is selected from Q 3time, R 5, R 6, R 7, R 8be selected from respectively H, fluorine, chlorine, bromine, NO 2, methyl or trifluoromethyl.
In the present invention, further preferred compound is, in general formula I:
Q is selected from Q 1, Q 2or Q 3;
When Q is selected from Q 1time, R 1, R 2be selected from respectively H, fluorine, chlorine, NO 2or trifluoromethyl, but R 1, R 2has one at least for H; X is selected from O or S;
When Q is selected from Q 2time, R 3, R 4be selected from respectively H, fluorine, chlorine, NO 2or trifluoromethyl, but R 3, R 4has one at least for H;
When Q is selected from Q 3time, R 5, R 6, R 7, R 8be selected from respectively H, fluorine, chlorine, NO 2or trifluoromethyl.
In the present invention, further preferred compound is again, in general formula I:
Q is selected from Q 1, Q 2or Q 3;
When Q is selected from Q 1time, R 1, R 2be selected from H, chlorine or trifluoromethyl, but R 1, R 2in have one for H; X is selected from O;
When Q is selected from Q 2time, R 3, R 4be selected from H, fluorine, chlorine, NO 2or trifluoromethyl, but R 3, R 4in have one for H;
When Q is selected from Q 3time, R 5be selected from H, fluorine or chlorine, R 6be selected from H, R 7be selected from chlorine or trifluoromethyl, R 8be selected from H or chlorine.
In the present invention, further preferred compound is, in general formula I:
Q is selected from Q 1or Q 2;
When Q is selected from Q 1time, R 1, R 2be selected from H or trifluoromethyl, but R 1, R 2in have one for H; X is selected from O;
When Q is selected from Q 2time, R 3, R 4be selected from H or trifluoromethyl, but R 3, R 4in have one for H.
In the definition of the compound of Formula I providing, collect term General Definition used as follows above:
Alkyl refers to straight or branched form, for example methyl, ethyl, n-propyl, isopropyl group.Haloalkyl refers to the group that alkyl is replaced by one or more halogen atoms, for example trifluoromethyl.Alkoxyl group refers to that alkyl end is connected with the group of Sauerstoffatom, such as methoxyl group, oxyethyl group, positive propoxy, isopropoxy etc.Halogenated alkoxy refers to that alkyl is replaced by one or more halogen atoms, and end is connected with the group of Sauerstoffatom, for example trifluoromethoxy.Halogen atom refers to fluorine, chlorine, bromine, iodine.
Compound of Formula I of the present invention can be prepared by the following method, and outside indicating, in reaction formula, each group definition is the same.
Work as Q=Q 1time:
Figure BSA00000297418600031
Work as Q=Q 2time:
Figure BSA00000297418600032
Work as Q=Q 3time:
Figure BSA00000297418600033
General formula I I, IV and V compound respectively with compound of formula III in suitable solvent, under suitable alkali exists, temperature makes target compound I-1, I-2 and I-3 for-10 ℃ for 0.5-48 hour to reacting under boiling point.
Suitable solvent is selected from methylene dichloride, chloroform, tetracol phenixin, hexane, benzene, toluene, ethyl acetate, acetonitrile, tetrahydrofuran (THF), dioxane, DMF or dimethyl sulfoxide (DMSO) etc.
Suitable alkali comprises that basic metal is if the hydrogen compound of lithium, sodium or potassium is as sodium hydride, and basic metal is if the oxyhydroxide of lithium, sodium or potassium is as sodium hydroxide, can also be alkali-metal carbonate as sodium carbonate, can be also that organic bases is as triethylamine, sodium tert-butoxide etc.
In the time of X=O, the preparation of general formula I I compound is carried out with reference to the operation of following document: J.Org.Chem.1996,61,3289-3297; Bioorganic & Medicinal Chemistry Letters 17 (2007) 4689-4693.
In the time of X=S, the preparation of general formula I I compound is carried out with reference to the operation of following document: J.Am.Chem.Soc.1927,49,1748-1758; ARKIVOC 2008 (xiv) 109-114.
Work as X=N-R 9time, general formula I I compound is with reference to the method preparation of CN1425665A (embodiment 5,7).
The preparation of compound of formula III is referring to the method for describing in CN1432555A.
The preparation of general formula I V compound is carried out with reference to the operation of following document: Journal of Medicinal Chemistry, 24 (1), 93-101; 1981; Journal of Medicinal Chemistry, 44 (11), 1785-1776; 2001.
Substituted pyridines shown in general formula V all has commercially available.
Table 1 to table 3 has been listed structure and the physical properties of part compound of Formula I.
Structure and the physical properties of table 1 part general formula I-1 compound
Figure BSA00000297418600041
Compound R 1 R 2 X Outward appearance (fusing point (℃))
1 H H O White solid (104-106)
2 CF 3 H O Yellow solid (68-70)
3 H Cl O White solid (125-127)
4 H CF 3 O White solid (56-58)
5 Cl Cl S
Structure and the physical properties of table 2 part general formula I-2 compound
Figure BSA00000297418600042
Compound R 3 R 4 Outward appearance (fusing point (℃))
6 H CF 3 White solid (116-118)
7 CF 3 H White solid (78-80)
8 H Cl White solid (143-145)
9 Cl H
10 F H
11 H F
12 H NO 2
13 NO 2 H
Structure and the physical properties of table 3 part general formula I-3 compound
Figure BSA00000297418600051
Compound R 5 R 6 R 7 R 8 Outward appearance (fusing point (℃))
14 Cl H Cl Cl White solid (101-103)
15 Cl H Cl H
16 F H Cl H
17 H H C1 H
18 Cl H CF 3 H
19 H H CF 3 H
Part of compounds 1h NMR (300MHz, CDCl 3) data are as follows:
Compound 1:4.56 (d, 2H), 4.78 (s, 2H), 5.19 (s, 2H), 6.10 (t, 1H), 6.79 (s, 2H), 7.20-7.27 (m, 2H), 7.37 (d, 1H), 7.51 (d, 1H).
Compound 2:4.57 (d, 2H), 4.78 (s, 2H), 5.22 (s, 2H), 6.10 (t, 1H), 6.80 (s, 2H), 7.48 (d, 2H), 7.77 (s, 1H).
Compound 3:4.56 (d, 2H), 4.78 (s, 2H), 5.18 (s, 2H), 6.10 (t, 1H), 6.81 (s, 2H), 7.24 (dd, 2H), 7.39 (d, 1H).
Compound 4:4.58 (d, 2H), 4.78 (s, 2H), 5.24 (s, 2H), 6.11 (t, 1H), 6.81 (s, 2H), 7.59 (d, 2H), 7.67 (s, 1H).
Compound 6:4.56 (d, 2H), 4.78 (s, 2H), 5.21 (s, 2H), 6.10 (t, 1H), 6.78 (s, 2H), 7.89-7.94 (m, 2H), 8.34 (s, 1H), 8.58 (s, 1H).
Compound 7:4.55 (d, 2H), 4.78 (s, 2H), 5.20 (s, 2H), 6.10 (t, 1H), 6.78 (s, 2H), 7.80 (d, 1H), 8.17 (d, 2H), 8.60 (s, 1H).
Compound 8:4.55 (d, 2H), 4.78 (s, 2H), 5.17 (s, 2H), 6.10 (t, 1H), 6.77 (s, 2H), 7.63 (dd, 1H), 7.77 (d, 1H), 8.02 (d, 1H), 8.50 (s, 1H).
Compound 14:4.59 (d, 2H), 4.78 (s, 2H), 5.05 (s, 2H), 6.12 (t, 1H), 6.82 (s, 2H), 7.75 (s, 2H).
Butyne ether compound of the present invention has high insecticidal activity to the insect such as beet armyworm, mythimna separata.Therefore, the present invention also comprises that compound of Formula I can be used for controlling the purposes of insect pest.
The present invention also comprises the insect-killing composition using compound of Formula I as active ingredient.In this insect-killing composition, the weight percentage of active ingredient is between 1-99%.In this insect-killing composition, also comprise acceptable carrier in agricultural, forestry, health.
Composition of the present invention can preparation form use.Compound of Formula I is easier to as solubilization of active ingredient or when being scattered in carrier or being mixed with preparation to using as desinsection disperse.For example: these chemicals can be made into wettable powder or missible oil.In these compositions, at least add a kind of liquid or solid carrier, and can add when needed suitable tensio-active agent.
Technical scheme of the present invention also comprises the method for pest control: insect-killing composition of the present invention is imposed on described insect or its growth medium.Conventionally the comparatively suitable significant quantity of selecting is 10 grams to 1000 grams of per hectares, and preferably significant quantity is 20 grams to 500 grams of per hectares.
For some application, for example in agricultural, can in insect-killing composition of the present invention, add one or more other sterilant, Insecticides (tech) & Herbicides (tech), plant-growth regulator or fertilizer etc., can produce thus additional advantage and effect.
Should be clear and definite, in claim limited range of the present invention, can carry out various conversion and change.
Embodiment
Following synthetic example, biological activity determination example can be used to further illustrate the present invention, but do not mean that restriction the present invention.
Synthetic example
The preparation of example 1 compound 2
Figure BSA00000297418600061
In reaction flask, add 4-(2, the chloro-4-(3 of 6-bis-, 3-bis-chloroallyloxyaminos) phenoxy group) (0.50 gram of fourth-2-alkynes-1-alcohol, 1.40 mmole, embodiment 1,2 in synthetic method referenced patent CN1432555A), tetrahydrofuran (THF) (10 milliliters), under room temperature, be stirred to dissolving, add 70% sodium hydride (0.10 gram, 2.80 mmoles), stir after 1 hour, add (0.31 gram of the chloro-5-trifluoromethyl of 2-benzo oxazole, 1.40 mmoles, synthetic method is with reference to J.Org.Chem.1996, and 67,3294), under room temperature, continue reaction 5 hours.Afterwards, by in reaction solution impouring water (50 milliliters), extract by ethyl acetate (3 × 150 milliliters), organic layer is used respectively saturated sodium bicarbonate aqueous solution (3 × 50 milliliters), saturated aqueous common salt (3 × 50 milliliters) washing, anhydrous magnesium sulfate drying, solvent is to the greatest extent steamed in decompression.Resistates is by the column chromatography (leacheate: ethyl acetate: sherwood oil=1: 100) obtain 0.16 and digest compound 2, outward appearance: yellow solid of purifying.Yield 18%.
The preparation of example 2 compounds 7
Figure BSA00000297418600062
In reaction flask, add 4-(2, the chloro-4-(3 of 6-bis-, 3-bis-chloroallyloxyaminos) phenoxy group) (0.50 gram of fourth-2-alkynes-1-alcohol, 1.40 mmoles), tetrahydrofuran (THF) (10 milliliters), under room temperature, be stirred to dissolving, add (0.10 gram of 70% sodium hydride, 2.80 mmole), stir after 1 hour, add the chloro-7-trifluoromethyl of 2-quinoxaline (0.32 gram, 1.40 mmoles, synthetic method is with reference to J.Med.Chem.1981,24 (1), 93), under room temperature, continue reaction 5 hours.Afterwards, by in reaction solution impouring water (50 milliliters), extract by ethyl acetate (3 × 150 milliliters), organic layer is used respectively saturated sodium bicarbonate aqueous solution (3 × 50 milliliters), saturated aqueous common salt (3 × 50 milliliters) washing, anhydrous magnesium sulfate drying, solvent is to the greatest extent steamed in decompression.Resistates is by the column chromatography (leacheate: ethyl acetate: sherwood oil=1: 100,1: 50) obtain 0.35 and digest compound 7, outward appearance: white solid of purifying.Yield 42%.
The preparation of example 3 compounds 14
Figure BSA00000297418600071
In reaction flask, add (0.50 gram of 4-(the chloro-4-of 2,6-bis-(3,3-, bis-chloroallyloxyaminos) phenoxy group) fourth-2-alkynes-1-alcohol, 1.40 mmoles), tetrahydrofuran (THF) (10 milliliters), under room temperature, be stirred to dissolving, add (0.10 gram of 70% sodium hydride, 2.80 mmoles), stir after 1 hour, add 2,3,5,6-4 chloro pyridine (0.30 gram, 1.40 mmoles, commercially available), under room temperature, continue reaction 5 hours.Afterwards, by in reaction solution impouring water (50 milliliters), extract by ethyl acetate (3 × 150 milliliters), organic layer is used respectively saturated sodium bicarbonate aqueous solution (3 × 50 milliliters), saturated aqueous common salt (3 × 50 milliliters) washing, anhydrous magnesium sulfate drying, solvent is to the greatest extent steamed in decompression.Resistates is by the column chromatography (leacheate: ethyl acetate: sherwood oil=1: 500) obtain 0.13 and digest compound 14, outward appearance: white solid of purifying.Yield 14%.
Other compound of Formula I of the present invention can be synthetic with reference to aforesaid method.
Biological activity determination example
The mensuration of example 4 insecticidal activities
According to the solvability of testing compound, dissolve former medicine with acetone or methyl-sulphoxide, then become 50 milliliters of the liquid to be measured of desired concn with 1 ‰ tween 80 solution preparation, acetone or the methyl-sulphoxide content in total solution is no more than 10%.
(1), the mensuration of killing beet noctuids activity
Adopt artificial diet medicine embrane method.Get 24 orifice plates, every hole adds 1 milliliter of the artificial diet that people prepares, after feed is cooling, with continous sample adding apparatus, according to test design, the order from low dosage to high dosage adds the liquid preparing, shake makes it form uniform medicine film on feed surface gently, naturally after drying in the shade, neat healthy the supplying of access tries insect, 1, every hole, totally 48 of every processing.Separately establish clear water and be treated to blank.After processing, put into 24 ℃, the indoor cultivation of relative humidity 60%～70%, unglazed photograph, 72 hours " Invest, Then Investigate " survival borer populations, calculate mortality ratio.
In the compound of part for examination, following compounds prevention effect to beet armyworm in the time that concentration is 50ppm is better, and mortality ratio is more than 80%: 2,6.
(2), the mensuration of mythimna separate
Maize leaf is cut into 4-5 cm long segment, processes with Airbrush spraying, certain density test compound liquid is sprayed in every leave dual sides, spouting liquid is 0.5 milliliter, separately establishes clear water and is treated to blank, and every processing repeats for 3 times.Every processing 8 examination worms of access (3 age) after drying in the shade.After processing, put into 24 ℃, the indoor cultivation of relative humidity 60%～70%, unglazed photograph, 72 hours " Invest, Then Investigate " survival borer populations, calculate mortality ratio.
In the compound of part for examination, following compounds prevention effect to mythimna separata in the time that concentration is 10ppm is better, and mortality ratio is more than 90%: 4,7.

Claims (4)

1. a Butyne ether compound, as shown in general formula I:
In formula:
Q is selected from Q as follows 1or Q 2:
Figure FSB0000123978240000012
Wherein:
Q is selected from Q 1or Q 2;
When Q is selected from Q 1time, R 1, R 2be selected from H or trifluoromethyl, but R 1, R 2in have one for H; X is selected from O;
When Q is selected from Q 2time, R 3, R 4be selected from H or trifluoromethyl, but R 3, R 4in have one for H.
2. one kind according to the purposes of compound of Formula I control agricultural claimed in claim 1 or forestry insect pest.
3. an insect-killing composition, containing compound shown in general formula I as claimed in claim 1 is acceptable carrier in active ingredient and agricultural or forestry, in composition, the weight percentage of active ingredient is 1-99%.
4. a method of controlling agricultural or forestry insect pest, is characterized in that: composition claimed in claim 3 is imposed on the insect of needs control or the medium of its growth with the effective dose of 10 grams to 1000 grams of per hectares.
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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996004228A1 (en) * 1994-08-04 1996-02-15 Sumitomo Chemical Company, Limited Dihalopropene compounds, insecticidal/acaricidal agents containing same, and intermediates for their production
CN1169147A (en) * 1994-10-14 1997-12-31 住友化学工业株式会社 Dihalopropene compounds, insecticidal/acaricidal agent contg. same, and intermediates
CN1209798A (en) * 1996-01-30 1999-03-03 住友化学工业株式会社 Dihalopropene compound, their use as insecticides/acaricides and intermediates

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996004228A1 (en) * 1994-08-04 1996-02-15 Sumitomo Chemical Company, Limited Dihalopropene compounds, insecticidal/acaricidal agents containing same, and intermediates for their production
CN1169147A (en) * 1994-10-14 1997-12-31 住友化学工业株式会社 Dihalopropene compounds, insecticidal/acaricidal agent contg. same, and intermediates
CN1209798A (en) * 1996-01-30 1999-03-03 住友化学工业株式会社 Dihalopropene compound, their use as insecticides/acaricides and intermediates

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Patentee before: Sinochem Corporation

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