CN1315778C - 1,2-disubstituted ally/arylox yphthalate compounds and use thereof - Google Patents
1,2-disubstituted ally/arylox yphthalate compounds and use thereof Download PDFInfo
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- CN1315778C CN1315778C CNB2005100472605A CN200510047260A CN1315778C CN 1315778 C CN1315778 C CN 1315778C CN B2005100472605 A CNB2005100472605 A CN B2005100472605A CN 200510047260 A CN200510047260 A CN 200510047260A CN 1315778 C CN1315778 C CN 1315778C
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 23
- -1 aryloxy benzoic acid Chemical compound 0.000 claims abstract description 25
- 241000196324 Embryophyta Species 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical class 0.000 claims abstract description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 230000012010 growth Effects 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 239000003337 fertilizer Substances 0.000 claims description 2
- 239000001963 growth medium Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000005648 plant growth regulator Substances 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 230000002363 herbicidal effect Effects 0.000 abstract description 11
- 230000000694 effects Effects 0.000 abstract description 5
- 230000008901 benefit Effects 0.000 abstract description 3
- 239000004009 herbicide Substances 0.000 abstract description 3
- 125000004953 trihalomethyl group Chemical group 0.000 abstract 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 2
- 239000005711 Benzoic acid Substances 0.000 abstract 2
- 235000010233 benzoic acid Nutrition 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 125000005245 nitryl group Chemical group [N+](=O)([O-])* 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001263 acyl chlorides Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 240000006995 Abutilon theophrasti Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 240000003307 Zinnia violacea Species 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000003449 preventive effect Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000009333 weeding Methods 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 238000005712 Baylis-Hillman reaction Methods 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
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 208000006278 hypochromic anemia Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
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- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The present invention relates to an aryloxy benzoic acid 1, 2-disubstituted allyl ester compound and an application thereof, which belongs to the technical field of herbicides and is characterized in that the aryloxy benzoic acid 1, 2-disubstituted allyl ester compound is represented by the general formula (I), wherein X represents H, halogen, trihalomethyl, alkyl, cyan groups or nitryl, X1 represents H, halogen or trihalomethyl, and X2 represents trihalomethyl or halogen; R1 represents phenyl, substituted phenyl or heterocyclic rings of C4 to C6, and R2 represents H, alkyl of C1 to C6, alkenyl of C3 to C6 or alkynyl of C3 to C6. Alkyl of the general formula (I) comprises linear alkyl or branched alkyl, and heterocyclic rings contain N, S, O, etc. The present invention has the effects and the advantages that the compound represented by the general formula (I) has herbicidal activity, and if used before and after sprouting, the compound can effectively control dicotyledonous weeds and monocotyledonous weeds. The compound has high herbicidal activity on gramineous weeds and broadleaf weeds.
Description
Technical field
The invention belongs to herbicide technology field, relate to a kind of fragrant oxybenzoic acid 1,2 two and replace allyl ester compounds and application thereof.
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 aryl formic acid compounds is as the existing report of weedicide (DE2311638, EP0020052).But as fragrant oxybenzoic acid 1,2 two replacement allyl ester compounds shown in the present is not seen open.
Summary of the invention
The invention provides a kind of fragrant oxybenzoic acid 1,2 two and replace the allyl ester compounds, shown in general formula I:
Wherein:
X is selected from H, halogen, trihalogenmethyl, alkyl, cyano group or nitro;
X
1Be selected from H, halogen, trihalogenmethyl;
X
2Be selected from trihalogenmethyl, halogen;
R
1Be selected from phenyl, substituted-phenyl, C
4-C
6Heterocycle;
R
2Be selected from H, C
1-C
6Alkyl, C
3-C
6Thiazolinyl or C
3-C
6Alkynyl;
The alkyl of indication comprises the straight or branched alkyl in the general formula I.Heterocycle is for containing N, S, O etc.
Comparatively preferred compound is a compound shown in general formula I I among the present invention:
Wherein:
R
1Be selected from phenyl, substituted-phenyl, C
4-C
6Heterocycle;
R
2Be selected from H, C
1-C
6Alkyl, C
3-C
6Thiazolinyl or C
3-C
6Alkynyl;
The alkyl of indication comprises the straight or branched alkyl among the general formula I I.Heterocycle is for containing N, S, O etc.
General formula compound I of the present invention can be prepared by following method:
With raw material (III can be buied by market) 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 IV for-10 ℃ in 0.5-48 hour to the following reaction of boiling point.
Acyl chlorides IV and compound V (according to method described in DE2155113, the US3742669, being obtained 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 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.
Table 1: the The compounds of this invention of part shown in general formula I I
| Compound | R 1 | R 2 | m.p. (℃) | IR υ max(cm -1) | 1H NMR(CDCl 3) δ(ppm) |
| 1 | Phenyl | Methyl | Oil | 3280，2960， 1735，1585， 1530，1520 | 8.00(d，J＝9.0Hz，1H)，7.81(d，J＝2.7 Hz，1H)，7.61(dd，J＝8.4Hz，2.7Hz， 1H)，7.41-7.33(m，5H)，7.23(d， J＝8.4Hz，1H)，7.1 3(d，J＝2.4Hz， 1H)，7.04(dd，J＝9.0Hz，2.4Hz，1H)， 6.91(s，1H)，6.47(s，1H)，5.87(s， 1H)，3.74(s，3H) |
| 2 | The 2,4 dichloro benzene base | Methyl | Oil | 3070，2950， 1740，1585， 1530 | 8.03(d，J＝9.0Hz，1H)，7.82(s，1H)， 7.63(d，J＝8.4Hz，1H)，7.43(s，1H)， 7.36(d，J＝8.4Hz，1H)，7.30-7.25(m， 2H)，7.19(s，1H)，7.15(s，1H)， |
| 7.07(d，J＝9.0Hz，1H)，6.55(s，1H)， 5.77(s，1H)，3.75(s，3H) | |||||
| 3 | The 2-thienyl | Methyl | Oil | 8.01(d，J＝9.0Hz，1H)，7.81(s，1H)， 7.61(d，J＝8.4Hz，1H)，7.32(d， J＝4.2Hz，1H)，7.24(d，J＝8.4Hz， 1H)，7.17-7.15(m，3H)，7.05(dd， J＝9.0Hz，2.4Hz，1H)，6.99(t， J＝4.2Hz，1H)，6.51(s，1H)，6.02(s， 1H)，3.77(s，3H) | |
| 4 | The 4-fluorophenyl | Methyl | Oil | 3070，2950， 1740，1580， 1530 | 7.99(d，J＝9.0Hz，1H)，7.81(s，1H)， 7.61(d，J＝8.4Hz，1H)，7.42-7.38(m， 2H)，7.24(d，J＝8.4Hz，1H)，7.15(d， J＝2.4Hz，1H)，7.08-7.02(m， 3H)，6.88(s，1H)，6.47(s，1H)， 5.29(s，1H)，3.73(s，3H) |
| 5 | The 2,4 dichloro benzene base | Ethyl | Oil | 3080，2980， 1745，1720， 1580，1530 | 8.02(d，J＝9.0Hz，1H)，7.82(s，1H)， 7.63(d，J＝8.4Hz，1H)，7.43(d， J＝1.5Hz，1H)，7.36(d，J＝8.4Hz， 1H)，7.30-7.25(m，2H)，7.21(s，1H)， 7.17(d，J＝2.7Hz，1H)，7.07(dd， J＝9.0Hz，2.7Hz，1H)，6.55(s， 1H)，5.78(s，1H)，4.19(q，6.9Hz， |
| 2H)，1.28(t，6.9Hz，3H) | |||||
| 6 | The 2-thienyl | Ethyl | Oil | 3070，2980， 1740，1730， 1530，1320 | 8.01(d，J＝9.0Hz，1H)，7.81(d， J＝1.8Hz，1H)，7.61(dd，J＝8.4Hz， 1.8Hz，1H)，7.32(d，4.8Hz， 1H)，7.24(d，J＝8.4Hz，1H)， 7.17-7.14(m，3H)，7.05(dd， J＝9.0Hz，3.0Hz，1H)，7.00-6.98(m， 1H)，6.50(s，1H)，5.99(s，1H)， 4.21(q，J＝6.9Hz，2H)，1.26(t， J＝6.9Hz，3H) |
| 7 | The 4-chloro-phenyl- | Ethyl | Oil | 3070，2980， 1740，1730， 1585，1530 | 7.99(d，J＝9.0Hz，1H)，7.81(d， J＝2.1Hz，1H)，7.61(dd，J＝8.4Hz， 2.1Hz，1H)，7.35(s，4H)，7.23(d， J＝8.4Hz，1H)，7.15(d，J＝3.0Hz， 1H)，7.05(dd，J＝9.0Hz，3.0Hz，1H)， 6.86(s，1H)，6.47(s，1H)，5.87(s， 1H)，4.16(q，J＝6.9Hz，2H)，1.24(t， 6.9Hz，3H) |
| 8 | The 4-nitrophenyl | Methyl | Oil | 3100，2980， 1740，1580， | 8.23(d，J＝8.4Hz，2H)，8.02(d， J＝9.0Hz，1H)，7.82(s，1H)， |
| 1525 | 7.63-7.60(m，3H)，7.27(d， J＝8.4Hz，1H)，7.18(d，J＝2.4Hz， 1H)，7.07(dd，J＝9.0Hz，2.4Hz，1H)， 6.95(s，1h)，6.53(s，1H)，5.97(s， 1H)，3.74(s，3H) | ||||
| 9 | The 4-aminomethyl phenyl | Methyl | Oil | 3280，2960， 1730，1585， 1530，1325， | 7.99(d，J＝9.0Hz，1H)，7.81(d， J＝2.1Hz，1H)，7.62-7.60(m，1H)， 7.29(d，J＝8.1Hz，2H)，7.23(d， J＝8.4Hz，1H)，7.17(d，J＝8.1Hz， 2H)，7.13(d，J＝2.7Hz，1H)， 7.04(dd，J＝9.0Hz，2.7Hz，1H)，6.88 (s，1H)，6.46(s，1H)，5.87(s，1H)， 3.73(s，3H)，2.35(s，3H) |
| 10 | The 2-chloro-phenyl- | Methyl | Oil | 3280，2960， 1730，1585， 1530，1320 | 8.04(d，J＝9.0Hz，1H)，7.82(d， J＝1.8Hz，1H)，7.62(dd，J＝8.4Hz， 1.8Hz，1H)，7.43-7.38(m，2H)， 7.33-7.24(m，4H)，7.15(d，J＝3.0Hz， 1H)，7.07(dd，J＝9.0Hz，3.0Hz，1H)， 6.56(s，1H)，5.75(s，1H)，3.76(s， 3H) |
| 11 | The 3-chloro-phenyl- | Methyl | Oil | 3280，2960， 1730，1585， 1530，1320 | 8.00(d，J＝9.0Hz，1H)，7.81(d， J＝1.8Hz，1H)，7.61(dd，J＝8.4Hz， 1.8Hz，1H)，7.43-7.34(m，3H)， 7.31(d，J＝1.5Hz，1H)，7.24(d， J＝8.4Hz，1H)，7.13(d，J＝3.0Hz， 1H)，7.04(dd，J＝9.0Hz，3.0Hz，1H)， 6.92(s，1H)，6.48(s，1H)，5.87(s， 1H)，3.75(s，3H) |
Effect of the present invention and benefit:
Compound of Formula I of the present invention has weeding activity, uses behind Miao Qianmiao and can effectively control single broadleaf weed.
The present invention also comprises with the compound of Formula I being 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.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 embodiment: 5-(2-chloro-4-(trifluoromethyl) benzene oxygen)-2-nitrobenzoic acid 2-(methoxycarbonyl)-1-phenyl allyl ester (compound 1):
In 250 milliliters reaction flask, add III-1 (11.6 grams, can be buied by market by 0.032 mole) and 150 milliliters of methylene dichloride, stir, add oxalyl chloride (6.1 grams, 0.048 mole), 2 DMF, stirring at room 5 hours, concentrate 11.0 gram acyl chlorides, outward appearance is yellow liquid (IV-1).
In 50 milliliters reaction flask, add V-1 (0.58 gram, 3.0 mmoles), triethylamine (0.46 gram), 5 milliliters of methylene dichloride stir the mixed solution that cooling drips IV-1 (1.2 grams, 3.2 mmoles) and 10 milliliters of methylene dichloride down, add half an hour approximately, reaction is 6 hours under the room temperature.Reaction finishes, in reaction solution, add 100 milliliters of methylene dichloride and 50 ml waters, separatory, dichloromethane layer is used saturated sodium bicarbonate aqueous solution, each 100 milliliters of washing of saturated sodium-chloride water solution successively, anhydrous magnesium sulfate drying concentrates, and is ethyl acetate with developping agent: the silica gel column chromatography separation of sherwood oil=1: 10, get the faint yellow oily thing of 1.3 grams, be 5-(2-chloro-4-(trifluoromethyl) benzene oxygen)-2-nitrobenzoic acid 2-(methoxycarbonyl)-1-phenyl allyl ester (compound 1).
1HNMR(CDCl
3)δ(ppm)8.00(d，J＝9.0Hz，1H)，7.81(d，J＝2.7Hz，1H)，7.61(dd，J＝8.4Hz，2.7Hz，1H)，7.41-7.33(m，5H)，7.23(d，J＝8.4Hz，1H)，7.13(d，J＝2.4Hz，1H)，7.04(dd，J＝9.0Hz，2.4Hz，1H)，6.91(s，1H)，6.47(s，1H)，5.87(s，1H)，3.74(s，3H)。IRυmax(cm
-1)3280，2960，1735，1585，1530，1520。
Other compounds in the table 1 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 compound liquid to be measured.Well-grown, broadleaf weeds of uniformity (youth-and-old-age, piemarker, 2-3 leaf phase) and gramineous weeds (lady's-grass are chosen in test, 1.5-2 the leaf phase) for supplying the examination target, carry out the cauline leaf spraying with track type crop atomizer and handle sprinkler height 30-45cm, spouting liquid 100ml/m
2, handle to be placed in the ventilation lobby and dry, in the greenhouse, cultivate according to a conventional method then.
Handling back 15d investigates.Inhibiting rate is the inhibition compared with the control or the preventive effect of various infringements such as chlorosis, withered spot, retarded growth or the calcination of leaf angle, and partial test the results are shown in Table 2.
Table 2: the weeding activity of compound in the general formula I
| Compound | Dosage ga.i./ha | Preventive effect % | ||
| Youth-and-old-age | Piemarker | Lady's-grass | ||
| 1 | 1000 | 100 | 100 | 80 |
| 2000 | 100 | 100 | 100 | |
| 2 | 200 | 90 | 85 | 90 |
| 1000 | 100 | 100 | 98 | |
| 2000 | 100 | 100 | 100 | |
| 3 | 40 | 95 | 95 | 50 |
| 200 | 100 | 100 | 75 | |
| 1000 | 100 | 100 | 90 | |
| 2000 | 100 | 100 | 100 | |
| 4 | 40 | 90 | 50 | 40 |
| 200 | 98 | 98 | 55 | |
| 1000 | 100 | 100 | 95 | |
| 2000 | 100 | 100 | 100 | |
| 5 | 40 | 80 | 40 | 20 |
| 200 | 95 | 95 | 80 | |
| 1000 | 100 | 100 | 95 | |
| 2000 | 100 | 100 | 100 | |
| 6 | 40 | 95 | 80 | 75 |
| 200 | 100 | 98 | 85 | |
| 1000 | 100 | 100 | 95 | |
| 2000 | 100 | 100 | 100 | |
| 7 | 40 | 90 | 10 | 10 |
| 200 | 95 | 25 | 75 | |
| 1000 | 98 | 90 | 98 | |
| 2000 | 100 | 100 | 100 | |
| 8 | 40 | 85 | 40 | 60 |
| 200 | 95 | 80 | 85 | |
| 1000 | 95 | 100 | 98 | |
| 2000 | 100 | 100 | 100 | |
| 9 | 200 | 80 | 90 | 70 |
| 1000 | 100 | 100 | 75 | |
| 2000 | 100 | 100 | 95 | |
| 10 | 1000 | 98 | 100 | 70 |
| 2000 | 98 | 100 | 95 | |
| 11 | 1000 | 100 | 100 | 75 |
| 2000 | 100 | 100 | 100 |
Claims (7)
1, a kind of fragrant oxybenzoic acid 1,2 two replaces the allyl ester compounds, shown in general formula I:
Wherein:
X is selected from H, halogen, trihalogenmethyl, alkyl, cyano group or nitro;
X
1Be selected from H, halogen, trihalogenmethyl;
X
2Be selected from trihalogenmethyl, halogen;
R
1Be selected from phenyl, substituted-phenyl, C
4-C
6Heterocycle;
R
2Be selected from H, C
1-C
6Alkyl, C
3-C
6Thiazolinyl or C
3-C
6Alkynyl;
Alkyl comprises the straight or branched alkyl in the general formula, and heterocycle is for containing N, S, O.
2, compound according to claim 1 is characterized in that, in the general formula I:
X is a chlorine;
X
1Be hydrogen;
X
2Be trifluoromethyl
R
1Be selected from phenyl, substituted-phenyl, C
4-C
6Heterocycle;
R
2Be selected from H, C
1-C
6Alkyl, C
3-C
6Thiazolinyl or C
3-C
6Alkynyl;
The alkyl of indication comprises the straight or branched alkyl in the general formula I, and heterocycle is for containing N, S, O.
3, contain right and require 1 described compound compositions, it is characterized in that the weight percentage of active ingredient in the composition is 1-99%, comprise acceptable liquid or solid carrier at least a agricultural in the composition.
4, the described compound of claim 1 is used to control weeds, it is characterized in that the independent use of compound or mixes use with other known sterilant, sterilant, plant-growth regulator or fertilizer.
5, the described composition of claim 3 is used to control weeds, it is characterized in that also can adding in the said composition one or more other weedicide.
6, use the described composition control of claim 3 method for weed, it is characterized in that composition imposes on the surface of the place of weeds surface, weed growth or weed growth medium.
7, using method according to claim 6 is characterized in that the significant quantity of selecting is that per hectare 10 restrains 5000 grams.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100472605A CN1315778C (en) | 2005-09-18 | 2005-09-18 | 1,2-disubstituted ally/arylox yphthalate compounds and use thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100472605A CN1315778C (en) | 2005-09-18 | 2005-09-18 | 1,2-disubstituted ally/arylox yphthalate compounds and use thereof |
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| Publication Number | Publication Date |
|---|---|
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| CN1315778C true CN1315778C (en) | 2007-05-16 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101407489B (en) * | 2007-10-09 | 2011-06-01 | 中国中化股份有限公司 | 2-alkyl acrylate compounds and uses thereof |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101096338B (en) * | 2006-06-28 | 2011-04-27 | 中国中化股份有限公司 | Benzoate compounds and uses thereof |
| CN101279951B (en) * | 2007-04-06 | 2010-09-01 | 中国中化股份有限公司 | 2-pyrimindinyloxy (pyrimindinylthio) benzoxy enoates compound and application thereof |
| CN115403488B (en) * | 2021-05-27 | 2024-07-19 | 江苏联化科技有限公司 | Preparation method of fomesafen |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4594100A (en) * | 1978-09-01 | 1986-06-10 | Rohm And Haas Company | Herbicidal 4-trifluoromethyl-4-nitrodiphenyl ethers |
| US5304531A (en) * | 1979-05-16 | 1994-04-19 | Basf Corp | Nitrodiphenyl ether herbicides |
| CN1411437A (en) * | 1999-12-22 | 2003-04-16 | 辛甄塔有限公司 | Process for preparation of diphenyl ether compounds |
-
2005
- 2005-09-18 CN CNB2005100472605A patent/CN1315778C/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4594100A (en) * | 1978-09-01 | 1986-06-10 | Rohm And Haas Company | Herbicidal 4-trifluoromethyl-4-nitrodiphenyl ethers |
| US5304531A (en) * | 1979-05-16 | 1994-04-19 | Basf Corp | Nitrodiphenyl ether herbicides |
| CN1411437A (en) * | 1999-12-22 | 2003-04-16 | 辛甄塔有限公司 | Process for preparation of diphenyl ether compounds |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101407489B (en) * | 2007-10-09 | 2011-06-01 | 中国中化股份有限公司 | 2-alkyl acrylate compounds and uses thereof |
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| CN1749236A (en) | 2006-03-22 |
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