CN1626526A - Compound of alpha, beta and beta, gamma unsaturation carboxylate class of possessing weeding activity - Google Patents
Compound of alpha, beta and beta, gamma unsaturation carboxylate class of possessing weeding activity Download PDFInfo
- Publication number
- CN1626526A CN1626526A CN 200310119043 CN200310119043A CN1626526A CN 1626526 A CN1626526 A CN 1626526A CN 200310119043 CN200310119043 CN 200310119043 CN 200310119043 A CN200310119043 A CN 200310119043A CN 1626526 A CN1626526 A CN 1626526A
- Authority
- CN
- China
- Prior art keywords
- compound
- beta
- alkyl
- alpha
- gamma
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 title claims description 30
- 150000007942 carboxylates Chemical class 0.000 title claims description 6
- 230000000694 effects Effects 0.000 title abstract description 8
- 238000009333 weeding Methods 0.000 title description 5
- 239000000203 mixture Substances 0.000 claims description 14
- 230000002363 herbicidal effect Effects 0.000 claims description 10
- 241000196324 Embryophyta Species 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 230000012010 growth Effects 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 150000001263 acyl chlorides Chemical class 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- -1 proyl Chemical group 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 239000003643 water by type Substances 0.000 description 3
- 240000006995 Abutilon theophrasti Species 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- 244000201986 Cassia tora Species 0.000 description 2
- 235000014552 Cassia tora Nutrition 0.000 description 2
- 244000058871 Echinochloa crus-galli Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 108010021119 Trichosanthin Proteins 0.000 description 2
- 240000003307 Zinnia violacea Species 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 241000981770 Buddleja asiatica Species 0.000 description 1
- 241000209510 Liliopsida Species 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 208000006278 hypochromic anemia Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 230000007226 seed germination Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
An unsaturated alpha, beta-and beta, gamma-carboxylate with high herbiciding activity is disclosed.
Description
Technical field
The invention belongs to the weedicide field.
Background technology
Because weedicide or its composition are in use for some time, weeds can produce resistance to it, therefore, need constantly invention novel with improved herbicidal compound and composition.In addition, consider the factor of aspects such as energy economy ﹠ environment, the invention weedicide different with existing herbicide action mechanism also is very important.
Some α, β and beta, gamma unsaturated carboxylate type compound are as the existing report of weedicide (USP6251829).But as alpha-substitution acidic group α shown in the present, β and beta, gamma unsaturated carboxylate type compound are not seen open.
Summary of the invention
The invention provides a kind of alpha-substitution acidic group α of novel structure, β and beta, gamma unsaturated carboxylate type compound, as general formula (I, II) shown in:
Wherein:
R is selected from H, C
1-C
6Alkyl, C
3-C
6Thiazolinyl or C
3-C
6Alkynyl;
Q is selected from one of group as follows:
R
1, R
2Be selected from H or C
1-C
4Alkyl;
And steric isomer.
Comparatively preferred compound is among the present invention:
R is selected from H, C
1-C
6Alkyl, C
3-C
6Thiazolinyl or C
3-C
6Alkynyl;
Q is selected from Q2,
R
2Be selected from C
1-C
4Alkyl,
And steric isomer.
More preferred structural formula of compound is as follows among the present invention:
In the formula, the carbon atom of mark * is the R type.
The alkyl of indication comprises the straight or branched alkyl in the general formula.Thiazolinyl is meant the straight or branched form, the group of 1 to 2 carbon-carbon double bond is arranged, for example vinyl, propenyl, allyl group etc.Alkynyl is meant the straight or branched form, and 1 to 2 carbon carbon triple-linked group, for example ethynyl, proyl, propargyl etc. are arranged.
General formula compound of the present invention (I II) can be prepared by following method:
With raw material (III can be buied by market) be dissolved in The suitable solvent, in alkaline aqueous solution, temperature reacted 0.5-48 hour down to boiling point for-10 ℃, again through hydrochloric acid or sulfuric acid acidation, making intermediate acid is compound (III-1).The suitable solvent is selected from as chloroform, methylene dichloride, tetracol phenixin, normal hexane, benzene, toluene, ethyl acetate, THF or dioxane; Suitable alkali is selected from sodium hydroxide, potassium hydroxide, yellow soda ash, salt of wormwood or sodium bicarbonate.
Intermediate acid (III-1) and SOCl
2, oxalyl chloride or PCl
3Be dissolved in The suitable solvent, for example chloroform, methylene dichloride, tetracol phenixin, normal hexane, benzene, toluene, ethyl acetate is in THF or the dioxane, with organic bases such as triethylamine, pyridine or DMF make catalyzer, and temperature made acyl chlorides (III-2) for-10 ℃ in 0.5-48 hour to the following reaction of boiling point.
Acyl chlorides (III-2) and 2-hydroxy-3-methyl-3-crotonate (can by buying on the market), in The suitable solvent, temperature be reacted down to boiling point and to be made product (I) in 0.5-48 hour for-10 ℃.Solvent can be 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 bicarbonates etc. are to reacting favourable.
Acyl chlorides (III-2) and 2-hydroxy-3-methyl-2-butylene acid esters (can by buying on the market) reaction can make product (II).The selection of reaction conditions and solvent, alkali is the same.
Table 1: the The compounds of this invention of part shown in general formula I
Compound Q R [α]
D 25Annotate
1
C
2H
5Oily matter
2
C
2H
5+ 18.84 R types, oily matter
3
C
2H
5Oily matter
Table 2: the The compounds of this invention of part shown in general formula I I
Compound Q R annotates
4????
??????????????????C
2H
5
5
C
2H
5The R type, oily matter
6????
?????????????????C
2H
5
Part of compounds in the table
1H NMR (CDCl
3) data are as follows:
Compound 1:7.361-7.330 (q, 1H), 7.284-7.252 (q, 1H), 7.118-7.065 (t, 1H), 5.502-5.500 (d, 1H), 5.397-5.218 (q, 2H), 5.191-5.082 (q, 1H), and 5.133-5.120 (q, 1H), 4.261-4.184 (q, 2H), 1.782-1.774 (q, 3H), and 1.281-1.239 (t, 3H)
Compound 2:8.672 (s, 1H), 8.049-8.041 (d, 1H), 7.696-7.667 (d, 1H), and 7.619-7.582 (q, 1H), 7.200-7.166 (m, 2H), 7.015-6.980 (m, 2H), 5.474-5.458 (d, 1H), 5.230-5.193 (q, 1H), and 5.151-5.126 (m, 1H), 4.938-4.859 (q, 1H), 4.242-4.207 (q, 2H), 1.808-1.793 (q, 3H), 1.764-1.703 (q, 3H), 1.271-1.254 (d, 3H)
Compound 3:7.35-7.30 (m, 2H), 7.15-7.05 (m, 6H), 5.65 (s, 1H), 5.30 (s, 1H), 5.18 (s, 2H), 4.65-4.60 (d, 1H), 4.32-4.22 (q, 2H), 3.50-3.45 (d, 1H), 1.80 (s, 3H), 1.35-1.28 (t, 3H)
(I, II) compound has weeding activity to general formula of the present invention, uses behind Miao Qianmiao and can effectively control single broadleaf weed.Compare with compound of the prior art, have the weeding activity of wide spectrum more.
The present invention comprises that also (I, II) compound is the herbicidal composition of active ingredient with general formula.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.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 significant quantity of selecting is that per hectare 10 restrains 5000 grams, and preferred significant quantity is that per hectare 50 restrains 2000 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 2:
In 500 milliliters reaction flask, add A (R type, 30.0 gram, can be buied by market by 0.0804 mole) and 80 milliliters of tetrahydrofuran (THF)s, be stirred to molten entirely, the solution that adds 3.2 gram sodium hydroxide and 80 ml waters, stirring at room 5 hours, stopped reaction, add 100 milliliters of ethyl acetate extractions, water concentrated hydrochloric acid acidifying, getting intermediate acid is white solid (B1), dry back weighs 25 grams.
In 250 milliliters reaction flask, add B1 (20.0 gram, 0.058 mole) and 150 milliliters of methylene dichloride, stir, add oxalyl chloride (11.0 grams, 0.087 mole), 3 DMF, stirring at room 4 hours concentrates to such an extent that 23 restrain acyl chlorides, and outward appearance is yellow liquid (C1).
In 50 milliliters reaction flask, add A1 (0.68 gram, 3.3 millis rub), triethylamine (0.56 gram), in 5 milliliters of dichloromethane solutions, stir the mixed solution that cooling drips C1 (1.0 grams, 2.75 millis rub) and 10 milliliters of methylene dichloride down, add half an hour approximately, reaction is 5 hours under the room temperature.Reaction is finished, in reaction solution, add 100 milliliters of ethyl acetate and 50 ml waters, separatory, ethyl acetate layer is used saturated sodium bicarbonate aqueous solution, each 100 milliliters of washing of saturated sodium-chloride water solution successively, and anhydrous magnesium sulfate drying concentrates, with developping agent is ethyl acetate: the silica gel column chromatography of sherwood oil=1: 10 separates, get the faint yellow oily thing of 1.5 grams, be compound 2, [α]
D 25:+18.84.
Other compounds in the table 1,2 can make by above similar method.
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 before the seedling: after planting carry out, test compound sparges soil surface, handles and is placed on the greenhouse, waters then; 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 broadleaf weed youth-and-old-age, piemarker and Cassia tora; Monocotyledon weed barnyard grass grass, dog tail and lady's-grass.
Examination material after the spraying drying places the greenhouse.Test is from the top water spray before the seedling, and test is poured water from the bottom and 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 3.
Table 3: the weeding activity of compound in the part general formula I
[before the seedling behind (2250 gram/hectare)/seedling (2250 gram/hectare)]
| Compound | The barnyard grass grass | Lady's-grass | Herba Setariae Viridis | Cassia tora | Piemarker | Youth-and-old-age |
| ????1 | ???0/0 | ???80/0 | ???50/0 | ???100/85 | ???100/95 | ??100/100 |
| ????2 | ???100/100 | ???100/100 | ???100/100 | ???10/85 | ???0/0 | ??0/0 |
| ????3* | ???60/90 | ???0/0 | ???80/85 | ???--** | ???0/90 | ??-- |
| ????5* | ???100/100 | ???100/100 | ???100/100 | ???-- | ???0/50 | ??-- |
Annotate *: the consumption of compound 3,5 is before the seedling behind (1200 gram/hectare)/seedling (1200 gram/hectare);
Annotate * *: do not survey.
Claims (6)
1, alpha-substitution acidic group α, β and beta, gamma unsaturated carboxylate type compound, as general formula (I, II) shown in:
Wherein:
R is selected from H, C
1-C
6Alkyl, C
3-C
6Thiazolinyl or C
3-C
6Alkynyl;
Q is selected from one of group as follows:
R
1, R
2Be selected from H or C
1-C
4Alkyl;
And steric isomer.
2, compound as claimed in claim 1 is characterized in that, in the general formula:
R is selected from H, C
1-C
6Alkyl, C
3-C
6Thiazolinyl or C
3-C
6Alkynyl;
Q is selected from Q2,
R
2Be selected from C
1-C
4Alkyl,
And steric isomer.
3, compound as claimed in claim 2 is characterized in that, is selected from the compound of following structure:
In the formula, the carbon atom of mark * is the R type.
4, a kind of herbicidal composition contains compound as claimed in claim 1 and agricultural goes up acceptable carrier, and the weight percentage of active ingredient is 1-99% in the composition.
5, the described compound of claim 1 or its composition are used to control the purposes of single broadleaf weed.
6, a kind of control method for weed is characterized in that: the herbicidal composition as claimed in claim 4 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 |
|---|---|---|---|
| CNB2003101190433A CN1301251C (en) | 2003-12-12 | 2003-12-12 | Compound of alpha, beta and beta, gamma unsaturation carboxylate class of possessing weeding activity |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2003101190433A CN1301251C (en) | 2003-12-12 | 2003-12-12 | Compound of alpha, beta and beta, gamma unsaturation carboxylate class of possessing weeding activity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1626526A true CN1626526A (en) | 2005-06-15 |
| CN1301251C CN1301251C (en) | 2007-02-21 |
Family
ID=34761286
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2003101190433A Expired - Lifetime CN1301251C (en) | 2003-12-12 | 2003-12-12 | Compound of alpha, beta and beta, gamma unsaturation carboxylate class of possessing weeding activity |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1301251C (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006125337A1 (en) * | 2005-05-23 | 2006-11-30 | Sinochem Corporation | α, β- AND, Ϝ-UNSATURATED CARBOXYLATES AND THE USE AS HERBICIDIDE THEREOF |
| CN100364955C (en) * | 2005-09-18 | 2008-01-30 | 大连理工大学 | 2-(dibasic) methyl acrylic ester compound and its use |
| CN100443475C (en) * | 2005-09-08 | 2008-12-17 | 沈阳化工研究院 | Compound of 2-substituted alkylacrylate and application thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6251829B1 (en) * | 2000-04-18 | 2001-06-26 | Rohm And Haas Company | Herbicidal benzoyloxy carboxylates and carboxamides |
-
2003
- 2003-12-12 CN CNB2003101190433A patent/CN1301251C/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006125337A1 (en) * | 2005-05-23 | 2006-11-30 | Sinochem Corporation | α, β- AND, Ϝ-UNSATURATED CARBOXYLATES AND THE USE AS HERBICIDIDE THEREOF |
| CN100443475C (en) * | 2005-09-08 | 2008-12-17 | 沈阳化工研究院 | Compound of 2-substituted alkylacrylate and application thereof |
| CN100364955C (en) * | 2005-09-18 | 2008-01-30 | 大连理工大学 | 2-(dibasic) methyl acrylic ester compound and its use |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1301251C (en) | 2007-02-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101279951B (en) | 2-pyrimindinyloxy (pyrimindinylthio) benzoxy enoates compound and application thereof | |
| CN101279950B (en) | 2-pyrimindinyloxy (pyrimindinylthio) benzoxy acetamide compound and application thereof | |
| CN101928271A (en) | 3-o-methylphenyl-2-oxo-1-oxaspiro[4,4]-n-3-ene-4-alcohol and derivatives thereof | |
| CN100386324C (en) | Compound of isobioquin group and application thereof | |
| CN1301251C (en) | Compound of alpha, beta and beta, gamma unsaturation carboxylate class of possessing weeding activity | |
| CN114409664B (en) | Spiro heterocyclic tetrahydropyran compound and preparation method and application thereof | |
| CN1927835A (en) | Compound of 2-benzoxyacrylate and application thereof | |
| CN1927843A (en) | Compound of 2-substituted alkylacrylate and application thereof | |
| CN100344628C (en) | Pyrazopyrimidinone compounds and use thereof | |
| CN1289494C (en) | Esters compound of dibenzanthracene-1,3-dioxa-cyclooctane-2-amine carboxylic acid of possessing weeding activity | |
| CN1233623C (en) | 2,6-dibromo-4-cyanophenyl ester compounds with herbicidal activity | |
| CN1127504C (en) | Herbicides of benzoyloxy unsaturated carboxylate type | |
| CN1233618C (en) | Benzoylcyclohexanone amine compounds with herbicidal activity | |
| CN1289493C (en) | Compound of dibenzanthracene-1,3-dioxa-cyclooctane-2-amide class of possessing weeding activity | |
| CN1033806A (en) | Pyridyl amide compound with fungicidal action | |
| CN100364955C (en) | 2-(dibasic) methyl acrylic ester compound and its use | |
| JP2008120711A (en) | Milbemycin derivative at position 27, having oxime group at position 13 | |
| CN1244536C (en) | Aroxyphenoxy carboxylic acid ester compounds with herbicidal activity | |
| CN1927811A (en) | Compound of 4-benzoxybutenolate and application thereof | |
| JPH0217191A (en) | Novel macrolide compound | |
| CN101096338B (en) | Benzoate compounds and uses thereof | |
| CN1128146C (en) | Dibenzo-1,3-dioxo-cyclooctane-2-oximino carboxylate compound with herbicidal activity | |
| CN100519508C (en) | 2-benzoyl-2-alkyl formyl radical acetic acid esters compounds and uses thereof | |
| CN110963963A (en) | Pyridine amide compound and sterilization application thereof | |
| CN101096342B (en) | 3-benzoic acid acrylate compound and uses thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| ASS | Succession or assignment of patent right |
Owner name: SINOCHEM CORPORATION; SHENYANG CHEMICAL ENGINEERI Free format text: FORMER OWNER: SHENYANG CHEMICAL ENGINEERING INST. Effective date: 20080711 |
|
| C41 | Transfer of patent application or patent right or utility model | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20080711 Address after: F6-F12, middle block, Kai Chen World Trade Centre, 28 Fuxing Man Street, Xicheng District, Beijing, China. Zip code: 100031 Co-patentee after: Shenyang Research Institute of Chemical Industry Patentee after: Sinochem Corp. Address before: No 8, Shen Liaodong Road, Tiexi District, Liaoning, Shenyang: 110021 Patentee before: Shenyang Research Institute of Chemical Industry |
|
| C56 | Change in the name or address of the patentee | ||
| CP03 | Change of name, title or address |
Address after: 28, Fuxing Man Street, Xicheng District, Beijing, China. Zip code: 100031 Co-patentee after: SHENYANG RESEARCH INSTITUTE OF CHEMICAL INDUSTRY Co.,Ltd. Patentee after: Sinochem Corp. Address before: 28, Fuxing Man Street, Xicheng District, Beijing, China. Zip code: 100031 Co-patentee before: Shenyang Research Institute of Chemical Industry Patentee before: Sinochem Corp. |
|
| ASS | Succession or assignment of patent right |
Owner name: CHINA SINOCHEM CO., LTD. Free format text: FORMER OWNER: SINOPEC CORPORATION Effective date: 20100108 |
|
| C41 | Transfer of patent application or patent right or utility model | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20100108 Address after: 28, Fuxing Man Street, Xicheng District, Beijing, China. Zip code: 100031 Co-patentee after: SHENYANG RESEARCH INSTITUTE OF CHEMICAL INDUSTRY Co.,Ltd. Patentee after: SINOCHEM Corp. Address before: 28, Fuxing Man Street, Xicheng District, Beijing, China. Zip code: 100031 Co-patentee before: SHENYANG RESEARCH INSTITUTE OF CHEMICAL INDUSTRY Co.,Ltd. Patentee before: Sinochem Corp. |
|
| C41 | Transfer of patent application or patent right or utility model | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20160122 Address after: 110021 Liaodong Road, Tiexi District, Liaoning, No. 8-1, No. Patentee after: SHENYANG SINOCHEM AGROCHEMICALS R&D Co.,Ltd. Address before: 28, Fuxing Avenue, Xicheng District, Beijing Patentee before: SINOCHEM Corp. Patentee before: SHENYANG RESEARCH INSTITUTE OF CHEMICAL INDUSTRY Co.,Ltd. |
|
| TR01 | Transfer of patent right | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20180615 Address after: 200120 Shanghai China (Shanghai) free trade pilot area No. 581 Shen Kuo road. Patentee after: SHANGHAI ZHONGHUA TECHNOLOGY Co.,Ltd. Address before: 110021 Shenyang Liaodong Road, Tiexi District, Shenyang, Liaoning 8-1 Patentee before: SHENYANG SINOCHEM AGROCHEMICALS R&D Co.,Ltd. |
|
| CX01 | Expiry of patent term | ||
| CX01 | Expiry of patent term |
Granted publication date: 20070221 |