CN1927843A - Compound of 2-substituted alkylacrylate and application thereof - Google Patents
Compound of 2-substituted alkylacrylate and application thereof Download PDFInfo
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- CN1927843A CN1927843A CN 200510047157 CN200510047157A CN1927843A CN 1927843 A CN1927843 A CN 1927843A CN 200510047157 CN200510047157 CN 200510047157 CN 200510047157 A CN200510047157 A CN 200510047157A CN 1927843 A CN1927843 A CN 1927843A
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Abstract
The present invention provides one kind of 2-substituted alkyl acrylate compound as shown in the general expression. The compound has herbicidal activity and may be used in controlling monocotylous weeds in seedling stage effectively.
Description
Technical field
The invention belongs to the weedicide field.
Background technology
Because the succession of weeds population, transition and to the drug-fast generation of chemical pesticide with develop rapidly; People to the reinforcement of ecological environmental protection consciousness and to chemical pesticide pollute, agricultural chemicals is to non-target organism influence and the attention of home to return to problem in the agricultural chemicals ecotope; World cultivated area reduces and the population growth strengthens the grain demand amount; Developing rapidly and reason such as updating of cropping system of agriculture production technology, need constantly invention novel with improved herbicidal compound and composition.Some acrylic ester compound is as weedicide (EP149034A2, USP6251829, CN1626526) existing report.But as 2-substituted alkylacrylate compound shown in the present is not seen open.
Summary of the invention
The invention provides a kind of 2-substituted alkylacrylate compound of novel structure, shown in general formula (I):
Wherein:
Q is selected from one of group as follows:
R
1Be selected from C
1-C
4Alkyl;
R
2Be selected from H, C
1-C
6Alkyl;
R
3Be selected from C
1-C
6Alkyl, C
3-C
6Thiazolinyl or C
3-C
6Alkynyl;
And steric isomer.
Above-mentioned general formula (I) compound is with R
1The mark that links to each other
*Chiral carbon atom be R, S configuration, or the mixture of its different ratios; Work as R
2When being not H, with R
2The mark that links to each other
*Chiral carbon atom be R, S configuration, or the mixture of its different ratios.
Comparatively preferred compound is in the general formula (I) among the present invention:
Q is selected from Q1, Q2 or Q5;
R
1Be selected from methyl;
R
2Be selected from H, C
1-C
6Alkyl;
R
3Be selected from C
1-C
6Alkyl.
Further preferred compound is in the general formula (I) among the present invention:
Q is selected from Q1, Q2 or Q5;
R
1Be selected from methyl, the mark that links to each other with methyl
*Chiral carbon atom be the R configuration;
R
2Be selected from H, C
1-C
6Alkyl is worked as R
2When being not H, with R
2The mark that links to each other
*Chiral carbon atom be R, S configuration, or the mixture of its different ratios;
R
3Be selected from C
1-C
4Alkyl.
The alkyl of indication comprises the straight or branched alkyl in the general formula (I).Thiazolinyl is meant the straight or branched form, and the group of 1 to 2 carbon-carbon double bond is arranged, for example, and propenyl, allyl group etc.Alkynyl is meant the straight or branched form, and 1 to 2 carbon carbon triple-linked group is arranged, for example, and proyl, propargyl etc.
General formula of the present invention (I) compound can be prepared by following method:
Raw material (II can be buied by market) is dissolved in the The suitable solvent, and joins in the alkaline aqueous solution, temperature is-10 ℃ reacted 0.5-48 hour under boiling point, and again through hydrochloric acid or sulfuric acid acidation, making intermediate acid is compound (III).Solvent is selected from chloroform, methylene dichloride, tetracol phenixin, normal hexane, benzene, toluene, ethyl acetate, THF or dioxane etc.; Alkali is selected from sodium hydroxide, potassium hydroxide, yellow soda ash, salt of wormwood or sodium bicarbonate etc.
Intermediate acid (III) and SOCl
2, oxalyl chloride or PCl
3Be dissolved in The suitable solvent, for example in chloroform, methylene dichloride, tetracol phenixin, normal hexane, benzene, toluene, ethyl acetate, THF or the dioxane etc., and with organic bases, make catalyzer as triethylamine, pyridine or DMF etc., temperature is-10 ℃ reacted 0.5-48 hour under boiling point, made intermediate acyl chlorides (IV).
Intermediate acyl chlorides (IV) and compound V are (according to method described in DE2155113, the US3742669, obtain by the Baylis-Hillman reaction by corresponding aldehyde and acrylate), in The suitable solvent, temperature made product (I) for-10 ℃ in 0.5-48 hour to the following reaction of boiling point.Solvent is selected from chloroform, methylene dichloride, tetracol phenixin, hexane, benzene, toluene, ethyl acetate, acetone, DMF, THF or dioxane etc.Add alkaloids, as triethylamine, pyridine, sodium hydroxide, potassium hydroxide, yellow soda ash, salt of wormwood, sodium bicarbonate etc. to reacting favourable.
General formula of the present invention (I) compound also can be prepared by following method:
Intermediate acid (III) and 2-(2-bromo substituted alkyl) acrylate (can by buying on the market or preparation according to a conventional method), in The suitable solvent, under the effect of suitable alkali ,-10 ℃ under the boiling point condition, react and made product (I) in 0.5-48 hour.Solvent is selected from chloroform, methylene dichloride, tetracol phenixin, hexane, benzene, toluene, ethyl acetate, acetone, DMF, acetonitrile, THF or dioxane etc.Alkali is selected from salt of wormwood, sodium hydroxide, potassium hydroxide, yellow soda ash, sodium bicarbonate, triethylamine, pyridine, sodium ethylate or sodium hydride etc.
The different starting raw materials or the difference of reaction conditions, might there be steric isomerism in general formula (I) compound.By selecting suitable starting raw material or control reaction conditions, can obtain excessive product of a kind of isomer or individual isomer.Work as R
2When being not H, in the product that obtains (I), can contain two kinds of diastereomers, can be by conventional separation means, for example method such as column chromatography, recrystallization obtains individual isomer.
Table 1: the The compounds of this invention of part shown in general formula (I)
| Compound | Q | R 1(C *Configuration) | R 2(R 2When being not H, C **Configuration) | R 3 | m.p.(℃) |
| 1 | Q 1 | CH 3(R) | H | CH 3 | 76～78 |
| 2 | Q 1 | CH 3(R) | CH 3(R/S or S/R=1.2) | CH 3 | 106～113 |
| 3 | Q 1 | CH 3(R) | Bu (R/S or S/R=1) | CH 3 | Wax |
| 4 | Q 1 | CH 3(R) | Bu (R or S) | CH 3 | 110～111 |
| 5 | Q 1 | CH 3(R) | Bu (R/S or S/R=0.6) | CH 3 | Wax |
| 6 | Q 2 | CH 3(R) | H | CH 3 | 87～89 |
| 7 | Q 2 | CH 3(R) | CH 3(R/S or S/R=1) | CH 3 | Wax |
| 8 | Q 5 | CH 3(R) | H | CH 3 | 50～52 |
| 9 | Q 2 | CH 3(R) | H | C 2H 5 | 61～62 |
Annotate: R
2When being not H, C
*Configuration (R/S or S/R) ratio can by
1H NMR analyzes and obtains, but can not judge absolute configuration.
General formula of the present invention (I) compound has weeding activity, uses behind seedling and can effectively control monocotyledon weed.
The present invention comprises that also with general formula (I) compound be the herbicidal composition of active ingredient.The weight percentage of active ingredient is 1-99% in this herbicidal composition.Comprise also in this herbicidal composition that agricultural goes up acceptable carrier.
Herbicidal composition of the present invention can several formulations form use.Usually with compound dissolution of the present invention or be scattered in and be mixed with preparation in the carrier so that be easier to disperse when using as weedicide.For example: these chemicals can be made into wettable powder or missible oil etc.Therefore, in these compositions, add a kind of liquid or solid carrier at least, and need to add suitable tensio-active agent usually.
Other embodiments of the present invention are method of controlling weeds, and this method comprises herbicidal composition of the present invention is imposed on the surface of the place of described weeds or described weed growth or its growth medium.Usually the comparatively suitable effective dose of selecting is that per hectare 1 restrains 1000 grams, and preferred effective dose is that per hectare 10 restrains 500 grams.Use for some, can in herbicidal composition of the present invention, add one or more other weedicide, can produce additional advantage and effect thus.
Compound of the present invention both can use separately also can be mixed together use with other known sterilant, sterilant, plant-growth regulator or fertilizer etc.
Should be clear and definite be in claim of the present invention institute restricted portion, can carry out various conversion and change.
Embodiment
The following example and living test are tested the result and be can be used to further specify the present invention, but do not mean that restriction the present invention.
Synthetic example
Synthesizing of compound 1:
(30.00 grams, 80.40 mmoles are purchased in Jiangsu Fengshan Group Co, mark to add quizalofopPethyl in 500 milliliters reaction flask
*Chiral carbon atom be the R configuration, down with) and 80 milliliters of tetrahydrofuran (THF)s, be stirred to moltenly entirely, (3.26 restrain to add sodium hydroxide, 80.68 mmole) and the solution that forms of water (80 milliliters), stirring at room reaction 5 hours, stopped reaction adds 100 milliliters of ethyl acetate extractions, water concentrated hydrochloric acid acidifying, filter, filtration cakes torrefaction gets white solid, i.e. intermediate acid 25.00 grams.
In 250 milliliters reaction flask, add above-mentioned intermediate acid (20.00 grams, 58.00 mmole) and 150 milliliters of methylene dichloride, stir and slowly add oxalyl chloride (11.00 grams down, 85.74 mmole), add 3 DMF again, the stirring at room reaction is after 4 hours, and methylene dichloride is deviate from decompression and excessive oxalyl chloride gets 23.00 gram yellow liquid, i.e. intermediate acyl chlorides.
In 50 milliliters reaction flask, add 2-hydroxyl methylene radical methyl acrylate (0.35 gram, 3.00 mmole), triethylamine (0.35 gram, 3.43 mmole) and in 5 milliliters of dichloromethane solutions, be added dropwise to above-mentioned intermediate acyl chlorides (1.25 grams under the ice-water bath, 3.40 mmole) and the solution that form of 10 milliliters of methylene dichloride, drip half an hour approximately, reaction is 5 hours under the room temperature, afterwards, adds 100 milliliters of ethyl acetate and 20 ml waters in reaction solution, separatory, ethyl acetate layer is used saturated sodium bicarbonate aqueous solution successively, each 20 milliliters of washing of saturated sodium-chloride water solution, anhydrous magnesium sulfate drying, decompression precipitation, separate (ethyl acetate/petroleum ether=1/5) through silica gel column chromatography, get 0.84 gram white solid, be compound 1, fusing point: 76～78 ℃.Nuclear-magnetism and infrared test data are as follows:
1H NMR(CDCl
3)δ(ppm)：8.67(s，1H)，8.05(d，J＝1.8Hz，1H)，7.69(d，J＝9.0Hz，1H)，7.60(dd，J＝9.0Hz，1.8Hz，1H)，7.18(d，J＝8.7Hz，2H)，6，95(d，J＝8.7Hz，2H)，6.37(s，1H)，5.79(s，1H)，4.99-4.81(m，3H)，3.76(s，3H)，1.67(d，J＝6.9Hz，3H)；
IR νmax(cm
-1)：3060，2950，1735，1510，1310。
Synthesizing of compound 3,4,5:
In 50 milliliters reaction flask, add 2-methylene radical-3-hydroxyl Methylheptanoate (0.52 gram, 3.00 mmole), triethylamine (0.35 gram, 3.43 mmole) and in 5 milliliters of dichloromethane solutions, be added dropwise to above-mentioned intermediate acyl chlorides (1.25 grams under the ice-water bath, 3.40 mmole) and the solution that form of 10 milliliters of methylene dichloride, drip half an hour approximately, reaction is 8 hours under the room temperature, afterwards, add 100 milliliters of ethyl acetate and 20 ml waters in reaction solution, ethyl acetate layer is used saturated sodium bicarbonate aqueous solution successively, each 20 milliliters of washing of saturated sodium-chloride water solution, anhydrous magnesium sulfate drying, the decompression precipitation, separate (ethyl acetate/petroleum ether=1/10) through silica gel column chromatography, get 0.76 gram wax, be compound 3.By
1H NMR analyzes its C
*Be configured as the mixture (R/S or S/R=1) of R type and S type, be a pair of diastereomer.
1H NMR(CDCl
3)δ(ppm)：8.68(s，1H)，8.67(s，1H)，8.06(d，J＝1.8Hz，2H)，7.67(d，J＝8.7Hz，2H)，7.61(dd，J＝8.7Hz，1.8Hz，2H)，7.17(d，J＝8.7Hz，4H)，6.94(d，J＝8.7Hz，4H)，6.32(s，1H)，6.22(s，1H)，5.81(s，1H)，5.48(s，1H)，5.69-5.65(m，2H)，4.81(q，J＝6.6Hz，2H)，3.78(s，3H)，3.75(s，3H)，1.72-1.63(m，10H)，1.26-1.11(m，8H)，0.91(t，J＝6.6Hz，3H)，0.81(t，J＝6.6Hz，3H)。
Top resulting equal proportion diastereomer compound 3 is used the benzene recrystallization, separate out white crystal earlier, be compound 4 (C
*Be configured as R type or S type), fusing point: 110～111 ℃.Nuclear-magnetism is determined structure.
1H NMR(CDCl
3)δ(ppm)：8.67(s，1H)，8.06(d，J＝1.8Hz，1H)，7.67(d，J＝8.7Hz，1H)，7.61(dd，J＝8.7Hz，1.8Hz，1H)，7.17(d，J＝8.7Hz，2H)，6.94(d，J＝8.7Hz，2H)，6.32(s，1H)，5.81(s，1H)，5.69-5.65(m，1H)，4.81(q，J＝6.6Hz，1H)，3.78(s，3H)，1.72-1.63(m，5H)，1.26-1.11(m，4H)，0.81(t，J＝6.6Hz，3H)。
Above-mentioned recrystallization mother liquor precipitation is got wax, be compound 5 (its C
*Be configured as the mixture of R type and S type, the isomer of one of them non-compound 4 excessive (R/S or S/R=0.6)).Nuclear magnetic data is as follows:
1H NMR(CDCl
3)δ(ppm)：8.68(s，1.25H)，8.67(s，0.75H)，8.06(d，J＝1.8Hz，2H)，7.67(d，J＝8.7Hz，2H)，7.61(dd，J＝8.7Hz，1.8Hz，2H)，7.17(d，J＝8.7Hz，4H)，6.94(d，J＝8.7Hz，4H)，6.32(s，0.75H)，6.22(s，1.25H)，5.81(s，0.75H)，5.48(s，1.25H)，5.69-5.65(m，2H)，4.81(q，J＝6.6Hz，2H)，3.78(s，2.25H)，3.75(s，3.75H)，1.72-1.63(m，10H)，1.26-1.11(m，8H)，0.91(t，J＝6.6Hz，3.75H)，0.81(t，J＝6.6Hz，2.25H)。
Synthesizing of compound 6:
(19.04 grams, 50.0 mmoles are purchased in Anhui Huaxing Chemical Co., Ltd., mark to add fenoxaprop in 500 milliliters reaction flask
*Chiral carbon atom be the R configuration, down with) and 100 milliliters of tetrahydrofuran (THF)s.Under the room temperature, the solution that dropping sodium (2.30 grams, 55.0 mmoles) and water (100 milliliters) form, stirring at room reaction 6 hours.Reaction finishes, and uses hcl acidifying, adds ethyl acetate extraction, and anhydrous magnesium sulfate drying, precipitation get the light brown solid, i.e. intermediate acid 17.00 grams.
In 250 milliliters reaction flask, add above-mentioned intermediate acid (2.67 grams, 8.00 mmole) and 40 milliliters of methylene dichloride, stir and slowly add oxalyl chloride (1.54 grams down, 12.00 mmole), add 2 DMF again, stirring at room reaction 4 hours, afterwards, methylene dichloride is deviate from decompression and excessive oxalyl chloride gets 2.79 gram yellow liquid, i.e. intermediate acyl chlorides.
In 50 milliliters reaction flask, add 2-hydroxyl methylene radical methyl acrylate (0.35 gram, 3.00 mmole), triethylamine (0.35 gram, 3.43 mmole) and in 5 milliliters of dichloromethane solutions, be added dropwise to above-mentioned intermediate acyl chlorides (1.19 grams under the ice-water bath, 3.40 mmole) and the solution that form of 10 milliliters of methylene dichloride, drip half an hour approximately, reaction is 5 hours under the room temperature, afterwards, adds 100 milliliters of ethyl acetate and 20 ml waters in reaction solution, separatory, ethyl acetate layer is used saturated sodium bicarbonate aqueous solution successively, each 20 milliliters of washing of saturated sodium-chloride water solution, anhydrous magnesium sulfate drying, decompression precipitation, separate (ethyl acetate/petroleum ether=1/5) through silica gel column chromatography, get 0.70 gram white solid, be compound 6, fusing point: 87～89 ℃.Nuclear-magnetism and infrared test data are as follows:
1H NMR(CDCl
3)δ(ppm)：7.44(d，J＝1.8Hz，1H)，7.41(d，J＝8.4Hz，1H)，7.32(d，J＝9.0Hz，2H)，7.25(dd，J＝8.4Hz，1.8Hz，1H)，6.95(d，J＝9.0Hz，2H)，6.37(s，1H)，5.80(s，1H)，4.96-4.85(m，2H)，4.79(q，J＝6.6Hz，1H)，3.77(s，3H)，1.65(d，J＝6.6Hz，3H)。
IR νmax(cm
-1)：3060，2940，1730，1500，1190。
Synthesizing of compound 8:
(15.00 grams, 40.0 mmoles are purchased in Shenyang Chemical Engineering Inst, mark to add haloxyfop-r-methyl in 250 milliliters reaction flask
*Chiral carbon atom be the R configuration, down with) and 60 milliliters of 2N aqueous sodium hydroxide solutions, be warming up to 70 ℃, stirring reaction 2 hours, stopped reaction.Reduce to room temperature, use the concentrated hydrochloric acid acidifying, add dichloromethane extraction, precipitation gets brown solid, i.e. intermediate acid 13.04 grams.
In 250 milliliters reaction flask, add above-mentioned intermediate acid (2.89 grams, 8.00 mmole) and 40 milliliters of methylene dichloride, stir and slowly add oxalyl chloride (1.54 grams down, 12.00 mmole), add 2 DMF again, stirring at room reaction 4 hours, afterwards, methylene dichloride is deviate from decompression and excessive oxalyl chloride gets 2.84 gram yellow liquid, i.e. intermediate acyl chlorides.
In 50 milliliters reaction flask, add 2-hydroxyl methylene radical methyl acrylate (0.35 gram, 3.00 mmole), triethylamine (0.35 gram, 3.43 mmole) and in 5 milliliters of dichloromethane solutions, be added dropwise to above-mentioned intermediate acyl chlorides (1.29 grams under the ice-water bath, 3.40 mmole) and the solution that form of 10 milliliters of methylene dichloride, drip half an hour approximately, reaction is 5 hours under the room temperature, afterwards, adds 100 milliliters of ethyl acetate and 20 ml waters in reaction solution, separatory, ethyl acetate layer is used saturated sodium bicarbonate aqueous solution successively, each 20 milliliters of washing of saturated sodium-chloride water solution, anhydrous magnesium sulfate drying, decompression precipitation, separate (ethyl acetate/petroleum ether=1/10) through silica gel column chromatography, get 0.69 gram white solid, be compound 8, fusing point: 50～52 ℃.Nuclear-magnetism and infrared test data are as follows:
1H NMR(CDCl
3)δ(ppm)：8.26(s，1H)，7.96(s，1H)，7.08(d，J＝8.7Hz，2H)，6.93(d，J＝8.7Hz，2H)，6.36(s，1H)，5.78(s，1H)，4.94-4.87(m，2H)，4.79(q，J＝6.9Hz，1H)，3.76(s，3H)，1.65(d，J＝6.9Hz，3H)；
IR νmax(cm
-1)：3060，2970，1730，1505，1325。
Synthesizing of compound 9:
The intermediate acid that adds fenoxaprop in 100 milliliters reaction flask (prepares with compound 6,2.20 gram, 6.25 mmole), salt of wormwood (1.00 grams, 7.17 mmole) and DMF (20 milliliters), behind the stirring reaction 10 minutes, add 2-brooethyl ethyl propenoate (1.35 grams, 6.65 mmole), reaction is after 1 hour under the room temperature, add 100 milliliters of ethyl acetate and 20 ml waters in reaction solution, ethyl acetate layer is used 2% aqueous hydrochloric acid successively, water, each the 20 milliliters of washing of saturated sodium bicarbonate aqueous solution and saturated sodium-chloride water solution, anhydrous magnesium sulfate drying, the decompression precipitation, separate (ethyl acetate/petroleum ether=1/5) through silica gel column chromatography, get 2.49 gram white solids, be compound 9.[α]
D 25(c=1.4, chloroform)=+ 28.6 °.The nuclear-magnetism test data is as follows:
1H NMR(300MHz CDCl
3)δ(ppm)：7.435(d，1H)，7.398(d，1H)，7.33-7.30(m，2H)，7.239(dd，1H)，6.97-6.94(m，2H)，6.362(d，1H)，5.782(d，1H)，4.906(q，2H)，4.794(q，1H)，4.228(q，2H)，1.654(d，3H)1.295(t，3H)。
Other compounds of general formula (I) can make by above similar method.
Other compounds in the table 1
1H NMR (CDCl
3, 300MHz), the IR data are as follows:
| Compound 2: compound 7: | 8.68 (s, 2H), 8.06 (d, J=1.8Hz, 2H), and 7.70-7.66 (m, 2H), 7.63-7.59 (m, 2H), 7.17 (d, J=9.0Hz, 4H), and 6.97-6.93 (m, 4H), 6.34 (s, 1.1H), 6.25 (s, 0.9H), 5.85 (s, 1.1H), 5.63 (s, 0.9H), 5.83-5.79 (m, 2H), and 4.83-4.75 (m, 2H), 3.78 (s, 3.3H), 3.74 (s, 2.7H), 1.70-1.65 (m, 6H), 1.46 (d, J=6.3Hz, 2.7H), 1.38 (d, J=6.3Hz, 3.3H).IR νmax(cm -1)：3060，2980，1730，1500，1305。7.44(d，J＝1.8Hz，2H)，7.41(d，J＝8.4Hz，2H)，7.31(d，J＝9.0Hz，4H)，7.25(dd，J＝8.4Hz，1.8Hz，2H)， 6.94(d，J＝9.0Hz，4H)，6.34(s，1H)，6.25(s，1H)，5.85(s，1H)，5.83-5.76(m，2H)，5.66(s，1H)， 4.79-4.70(m，2H)，3.78(s，3H)，3.74(s，3H)，1.64(d，J＝6.9Hz，6H)，1.45(d，J＝6.3Hz，3H)， 1.37(d，J＝6.3Hz，3H)。IR νmax(cm -1)：3070，2990，1740，1500，1190。 |
Give birth to and survey example
With the former medicine of acetone solution, by design dosage, join in the certain water gaging that contains tensio-active agent, make certain density preparation.Spray with mobile belt atomizer.The examination material is put in spraying rolling in the cupboard and is with, and mobile shower nozzle is sprayed onto medicament on the examination material with the covering of the fan Sprayable through examination material top, identical on nozzle and the common field spray device.Roll band and will try material and shift out outside the cupboard, place loft drier dry.
Test behind the seedling, seed germination also grew 10-21 days, made the examination material that has a series of growing stages before the processing, selected size, the consistent examination material of growing stage then, handled, and handled to be placed on the greenhouse and to water.The examination material with compound treatment does not compare.The examination material is monocotyledon weed barnyard grass grass and lady's-grass.
Examination material after the spraying drying places the greenhouse.Test is poured water from the bottom and was kept 48 hours so that water does not touch the blade face behind the seedling.
Handling the back investigated in 4 weeks.Inhibiting rate is total effect of various infringements such as chlorosis, withered spot, retarded growth or the calcination of leaf angle, obtains the result with blank after relatively.Partial test the results are shown in Table 2.
Table 2: the weeding activity of compound in the part general formula I (behind the seedling, inhibiting rate %)
| Compound | Dosage (gram/hectare) | The barnyard grass grass | Lady's-grass |
| 1 | 200 | 100 | 100 |
| 40 | 98 | * | |
| 10 | 75 | ||
| 2 | 200 | 98 | 100 |
| 40 | 35 | 60 | |
| 4 | 200 | 100 | 98 |
| 40 | 100 | 80 | |
| 10 | 80 | ||
| 5 | 200 | 100 | 100 |
| 40 | 70 | ||
| 6 | 200 | 100 | 90 |
| 40 | 98 | ||
| 10 | 70 | ||
| 7 | 200 | 100 | 98 |
| 40 | 100 | ||
| 10 | 90 | ||
| 8 | 200 | 90 | 98 |
| 40 | 90 | 98 | |
| 9 | 480 | 90 | 90 |
| 120 | 90 | 80 | |
| 30 | 80 | 60 |
*: the space is represented not survey
Claims (6)
1, a kind of 2-substituted alkylacrylate compound, shown in general formula (I):
In the formula:
Q is selected from one of group as follows:
R
1Be selected from C
1-C
4Alkyl;
R
2Be selected from H, C
1-C
6Alkyl;
R
3Be selected from C
1-C
6Alkyl, C
3-C
6Thiazolinyl or C
3-C
6Alkynyl;
And steric isomer.
2, compound as claimed in claim 1 is characterized in that, in the general formula (I):
Q is selected from Q1, Q2 or Q5;
R
1Be selected from methyl;
R
2Be selected from H, C
1-C
6Alkyl;
R
3Be selected from C
1-C
6Alkyl;
And steric isomer.
3, compound as claimed in claim 1 is characterized in that, in the general formula (I):
Q is selected from Q1, Q2 or Q5;
R
1Be selected from methyl, the chiral carbon atom of the mark * that links to each other with methyl is the R configuration;
R
2Be selected from H, C
1-C
6Alkyl is worked as R
2When being not H, with R
2The chiral carbon atom of the mark * * that links to each other is R, S configuration, or the mixture of its different ratios;
R
3Be selected from C
1-C
4Alkyl.
4, the described compound of claim 1 is used to control the purposes of weeds.
5, a kind of herbicidal composition contains the described general formula of claim 1 (I) compound and agricultural goes up acceptable carrier, and the weight percentage of active ingredient is 1-99% in the composition.
6, a kind of control method for weed is characterized in that: the herbicidal composition as claimed in claim 5 of using herbicidally effective amount on the growth mediums of weeds or weeds or place.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100471570A CN100443475C (en) | 2005-09-08 | 2005-09-08 | Compound of 2-substituted alkylacrylate and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100471570A CN100443475C (en) | 2005-09-08 | 2005-09-08 | Compound of 2-substituted alkylacrylate and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1927843A true CN1927843A (en) | 2007-03-14 |
| CN100443475C CN100443475C (en) | 2008-12-17 |
Family
ID=37857997
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2005100471570A Expired - Fee Related CN100443475C (en) | 2005-09-08 | 2005-09-08 | Compound of 2-substituted alkylacrylate and application thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103086995A (en) * | 2013-02-01 | 2013-05-08 | 湖南大学 | 2-[4-(benzoxazole-2-oxygroup) phenoxy] alkylamide and application thereof |
| CN104649995A (en) * | 2013-11-25 | 2015-05-27 | 中国中化股份有限公司 | 6-chlorobenzoxazole oxygen phenoxypropionic acid allyl ester compound and application thereof as weeding agent |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1281602C (en) * | 2003-09-29 | 2006-10-25 | 沈阳化工研究院 | Novel carboxylate herbicides |
| CN1301251C (en) * | 2003-12-12 | 2007-02-21 | 沈阳化工研究院 | Compound of alpha, beta and beta, gamma unsaturation carboxylate class of possessing weeding activity |
-
2005
- 2005-09-08 CN CNB2005100471570A patent/CN100443475C/en not_active Expired - Fee Related
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103086995A (en) * | 2013-02-01 | 2013-05-08 | 湖南大学 | 2-[4-(benzoxazole-2-oxygroup) phenoxy] alkylamide and application thereof |
| CN103086995B (en) * | 2013-02-01 | 2014-08-13 | 湖南大学 | 2-[4-(benzoxazole-2-oxygroup) phenoxy] alkylamide and application thereof |
| CN104649995A (en) * | 2013-11-25 | 2015-05-27 | 中国中化股份有限公司 | 6-chlorobenzoxazole oxygen phenoxypropionic acid allyl ester compound and application thereof as weeding agent |
| CN104649995B (en) * | 2013-11-25 | 2017-06-09 | 沈阳中化农药化工研发有限公司 | A kind of 6 chloro benzo oxazole epoxide phenoxy propionic acid allyl ester type compound and its application as herbicide |
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| CN100443475C (en) | 2008-12-17 |
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