CN1167693C - Herbicidal (4-Cl-2-O-benzothiazolyline-3-group) alkyl carboxylic ester compounds - Google Patents
Herbicidal (4-Cl-2-O-benzothiazolyline-3-group) alkyl carboxylic ester compounds Download PDFInfo
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- CN1167693C CN1167693C CNB011280778A CN01128077A CN1167693C CN 1167693 C CN1167693 C CN 1167693C CN B011280778 A CNB011280778 A CN B011280778A CN 01128077 A CN01128077 A CN 01128077A CN 1167693 C CN1167693 C CN 1167693C
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Abstract
The present invention relates to a (4-chlorine-2-O-benzothiazoline-3-group) alkyl carboxylic ester compound with herbicidal activity, wherein the (4-chlorine-2-O-benzothiazoline-3-group) alkyl carboxylic ester compound has a general formula that: R1, R2, R3 and R4 are H, (C1-C4) alkyl group, halogenating (C1-C4) alkyl group, halogen, CN or NO2; m is equal to 2-10, and Q is H, halogen, substituted phenoxy group or substituted heterocycle oxyl group.
Description
Technical field
The present invention relates to a kind of (4-chloro-2-oxygen-benzothiazole quinoline-3-yl) alkyl carboxylic ester compounds and uses 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 (4-chloro-2-oxygen-benzothiazole quinoline-3-yl) alkyl carboxylic ester compounds as weedicide (Chem.Pap., 1994,48 (3), 195-197), the existing report of English Patent (Brit.Patent 862226,1959).But do not see open as containing the substituent compound of benzene on the alcohol groups among (4-chloro-2-oxygen-benzothiazole quinoline-3-yl) alkyl carboxylic acid ester shown in the present.
Summary of the invention
The invention provides a kind of new (4-chloro-2-oxygen-benzothiazole quinoline-3-yl) alkyl carboxylic ester compounds and steric isomer, its composition and acceptable carrier thereof, as broad-spectrum herbicide, behind Miao Qianmiao, use and effectively to control weeds, especially monocotyledon weed is had tall and erect the effect.The present invention also relates to these compounds of preparation, uses the method that these compounds carry out weeding.
Compound provided by the present invention is shown in general formula (I):
Wherein:
R
1, R
2Be H, (C
1-C
4) alkyl or halo (C
1-C
4) alkyl;
R
3, R
4Be H, halogen, CN, NO
2, (C
1-C
4) alkyl or halo (C
1-C
4) alkyl;
m＝2-10；
Q is H, halogen, CN, NO
2, (C
1-C
4) alkyl, halo (C
1-C
4) alkyl, Q1, Q2, Q3 or Q4:
R
5, R
6Be H, halogen, (C
1-C
4) alkyl or halo (C
1-C
4) alkyl;
R
7, R
8Be H, halogen, CN, NO
2, (C
1-C
4) alkyl or halo (C
1-C
4) alkyl;
R
9, R
10Be H, halogen, CN, NO
2, (C
1-C
4) alkyl or halo (C
1-C
4) alkyl;
X=O, N or S;
And steric isomer.
Comparatively preferred compound is in the general formula (I) among the present invention:
R
1, R
2Be H or CH
3
R
3, R
4Be H, halogen, CN, (C
1-C
4) alkyl or halo (C
1-C
4) alkyl;
m＝2-6；
Q is H, halogen, and Q1, Q2, Q3 or Q4:
R
5, R
6Be H, halogen, (C
1-C
4) alkyl or halo (C
1-C
4) alkyl;
R
7, R
8Be H, halogen, CN or halo (C
1-C
4) alkyl;
R
9, R
10Be H or halogen;
X=O, N or S;
And steric isomer.
Further preferred compound is in the general formula (I) among the present invention:
R
1, R
2Be H or CH
3
R
3, R
4Be H, halogen, CN or methyl;
m＝2-4；
Q is H, halogen, Q1 or Q2
R
5, R
6Be H, halogen or methyl;
R
7, R
8Be H, halogen, CN, methyl or CF
3
And steric isomer.
Further preferred compound is in the general formula (I) among the present invention:
R
1, R
2Be H or CH
3
R
3, R
4Be H, halogen, CN or methyl;
m＝2-4；
Q is Q1
R
5, R
6Be H, halogen or methyl;
And steric isomer.
So-called alkyl is meant the straight or branched form, for example groups such as methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, isobutyl-, middle butyl, tertiary butyl.
So-called alkylhalide group is meant the group that alkyl is replaced by one or more halogen atoms.
So-called halogen is meant fluorine, chlorine, bromine, iodine.
General formula compound of the present invention (I) can be prepared by following method:
Intermediate acid (II) (can make by currently known methods) and SOCl referring to US3888871
2, oxalyl chloride or PCl
3Be dissolved in The suitable solvent, chloroform for example, methylene dichloride, tetracol phenixin, normal hexane, benzene, toluene, ethyl acetate, THF, or dioxane, and at organic bases such as triethylamine, under pyridine or the DMF condition as catalyzer, temperature made compound (II-1) for-10 ℃ in 0.5-48 hour to the following reaction of boiling point.
Acyl chlorides (II-1) and alkane glycol (can by buying on the market) be in The suitable solvent, and temperature is reacted down to boiling point and to be made compound (II-2) 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) and compound (II-2) are in The suitable solvent, and temperature made compound (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.
Wherein acyl chlorides (III) can be made by following formula:
Fortified phenol (III-1) and alpha-halogen alkyl carboxylic acid or its ester (L is bromine or chlorine) or α-Phenylsulfonic acid substituted alkyl carboxylic acid or its ester (L is the Phenylsulfonic acid base) are dissolved in the The suitable solvent, chloroform for example, methylene dichloride, tetracol phenixin, normal hexane, benzene, toluene, ethyl acetate, acetone, DMF, THF, dioxane, water, ethanol or Virahol, and at alkali such as triethylamine, pyridine, sodium hydroxide, potassium hydroxide, yellow soda ash, salt of wormwood, cesium carbonate or sodium hydride exist down, and temperature is reacted down to boiling point and to be made compound (III-2) in 0.5-100 hour for-10 ℃.If product is an ester, can be by currently known methods, at alkali such as sodium hydroxide, yellow soda ash etc. exist down, as water, make compound (III-2) in reaction 0.5-24 such as alcohol hour in the The suitable solvent.
Intermediate acid (III-2) and SOCl
2, oxalyl chloride or PCl
3Be dissolved in The suitable solvent, chloroform for example, methylene dichloride, tetracol phenixin, normal hexane, benzene, toluene, ethyl acetate, THF, or dioxane, and at organic bases such as triethylamine, under pyridine or the DMF condition as catalyzer, temperature made acyl chlorides (III) for-10 ℃ in 0.5-48 hour to the following reaction of boiling point.
General formula compound of the present invention (I) also can be prepared by following method:
Acyl chlorides (III) and alkane glycol (can by buying on the market) be in The suitable solvent, and temperature is reacted down to boiling point and to be made compound (III-3) 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 (II-1) and compound (III-3) are in The suitable solvent, and temperature made compound (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
Compound R
1R
2R
3R
4Q m mp (℃)
1 H H H H H 2 68-78
2 H H H H 4-Cl 2 82-85
3 H H 2-Cl H 4-Cl 2 82-86
4 H H 2-CH
3 H 4-Cl 2 112-115
5 H CH
3H H H 2 oily matter
6 H CH
3H H Q1 2 half solid shapes
7 H CH
3 H H Q2 2
8 H CH
3H H Q4 2 oily matter
9 H H H H H, 3 oily matter
10 H H 2-Cl H 4-Cl, 3 oily matter
11 H H 2-CH
3H 4-Cl 3 oily matter
12 H CH
3H H H 3 oily matter
13 H CH
3H H Q1 3 oily matter
14 H CH
3 H H Q2 3
15 H CH
3H H Q4 3 oily matter
Annotate 1: in the compound 6 and 13, the R among the Q1
5=2-Cl, R
6=4-Cl
Annotate 2: in the compound 7 and 14, the R among the Q2
7=5-CF
3, R
8=H
Annotate 3: in the compound 8 and 15, the R among the Q4
10=6-Cl
Part of compounds in the table 1
1H NMR (CDCl
3) data are as follows:
Compound 5:7.24-6.67 (m, 8H), 5.02 (s, 2H), 4.66 (q, 1H), 4.29 (s, 4H), 1.57 (d, 3H)
Compound 6:7.27-6.47 (m, 10H), 5.04 (s, 2H), 4.6 (q, 1H), 4.30 (s, 4H), 1.55 (d, 3H)
Compound 8:8.66 (s, 1H), 8.03 (s, 1H), 7.66-6.94 (m, 5H), 5.14 (s, 2H), 4.78 (q, 1H),
4.16(s，4H)，1.63(d，3H)
Compound 9:7.37-6.89 (m, 8H), 5.16 (s, 2H), 4.64 (s, 2H), 4.25-4.20 (m, 4H), 2.01 (t, 2H)
Compound 10:7.26-6.58 (m, 6H), 5.06 (s, 2H), 4.63 (s, 2H), 4.23-3.92 (m, 4H), 1.97 (t, 2H)
Compound 11:7.25-6.41 (m, 6H), 5.05 (s, 2H), 4.53 (s, 2H), 4.23-4.05 (m, 4H), 2.21 (s, 3H),
1.96(t，2H)
Compound 12:7.43-6.8 (m, 8H), 5.14 (s, 2H), 4.79 (q, 1H), 4.17-4.11 (m, 4H), 1.94 (t, 2H),
1.66(d，3H)
Compound 13:7.27-6.47 (m, 10H), 5.04 (s, 2H), 4.6 (q, 1H), 4.10 (t, 4H), 1.93 (m, 2H),
1.58(d，3H)
Compound 15:8.67 (s, 1H), 8.04 (s, 1H), 7.68-6.93 (m, 5H), 5.15 (s, 2H), 4.8 (q, 1H),
4.25-4.11(m，4H)，2.0(t，2H)，1.65(d，3H)
The present invention also comprises the herbicidal composition of being made up of compound with weeding activity shown in the general formula (I) and carrier that contains (4-chloro-2-oxygen-benzothiazole quinoline-3-yl) alkyl carboxylic ester compounds.
Other embodiments of the present invention are method of controlling weeds, and this method comprises that (4-chloro-2-oxygen-benzothiazole quinoline-3-yl) alkyl carboxylic ester herbicidal composition that compound shown in the general formula of herbicidally effective amount (I) and acceptable carrier are formed imposes on the surface of growth medium of the places of described weeds or described weeds or described weeds.
(4-chloro-2-oxygen-benzothiazole quinoline-3-yl) alkyl carboxylic ester compounds of the present invention and composition thereof can be used as emerge before and emerge the back weedicide.
Compound of the present invention can preparation form be administered on soil or the blade face.This compound is dissolved in the carrier usually or is mixed with preparation so that be easier to disperse when using as weedicide.For example: but these chemicals can be made into wet-milling, emulsifiable concentrate, pulvis, suspension concentrate, smoke substance or missible oil.In these compositions, added a kind of liquid or solid carrier and when needs, can mix suitable tensio-active agent.
Generally, particularly when on leaf, spraying, wish to contain in the composition auxiliary in the actually operating, as wetting agent, spreading agent, dispersion agent, tackiness agent, tackiness agent etc.Be common to this class auxiliary of this area, can be at the John W.McCutcheon, the publication Detergents and Emulsifiers of company, Annual.Allured PublishingCompany, Ridgewood, New Jersey finds among the U.S.A..
(4-chloro-2-oxygen-benzothiazole quinoline-3-yl) of the present invention alkyl carboxylic ester compounds herbicidal composition can be used with the form of herbicide sprays by method commonly used, for example use traditional heavy body hydraulic atomizing, lower volume hydraulic atomizing, gas blowout mist, air-spraying or dusting.Extent of dilution and consumption will depend on the type of equipment used, the method for using and the weeds that will control, but the comparatively suitable significant quantity of selecting usually is that per hectare 100 restrains 5000 grams, and preferred significant quantity is that per hectare 200 restrains 3000 grams.
(4-chloro-2-oxygen-benzothiazole quinoline-3-yl) of the present invention alkyl carboxylic ester compounds herbicidal composition can mix with fertilizer before using mutually.Used in the solid fertilizer composition of said (4-chloro-2-oxygen-benzothiazole quinoline-3-yl) alkyl carboxylic ester compounds in a class, fertilizer or getting fat component as ammonium sulfate, ammonium nitrate or ammonium phosphate, can have been applied with one or more compounds.Said solid chemical compound or solid fertilizer also can mix in mixing equipment, and perhaps they can be combined into granular composition with fertilizer.Fertilizer can use any ratio, but generally said (4-chloro-2-oxygen-benzothiazole quinoline-3-yl) alkyl carboxylic ester compounds ratio in its Ru 2006101161 is about 5% to 25%.These compositions have been controlled the growth that does not need plant when fertilizer is provided, promotes required plant growth.Compound of the present invention can exist with the form of composition or preparation." pesticide preparation research " (publishing in 1969) that preparation preparation or method for compositions can be published with reference to American Chemical Society or chemical progress series of books " pesticide preparation) " (publication in 1973).So-called preparation is meant thinner or the solid carrier of dispersion agent and the mixture of liquid vehicle that active ingredient and agrotechnique are suitable for.Carrier is meant to have emulsifying effect, dissemination and diluting effect, do not damage the active ingredient effect and soil, equipment, crop and agricultural environment are not had the composition of influence, also need add auxiliary agent such as tensio-active agent, stablizer, defoamer or antisettling agent sometimes.
So-called composition or formulation example such as the aqueous solution or aqueous dispersions, oil solution or oily dispersion liquid, paste, pulvis, wettable powder, emulsifiable concentrate, granule, attractive substance, smoke substance etc.Wettable powder, emulsifiable concentrate, paste are prepared also dilute with water before use with high density.In these preparations, can contain the liquid or solid carrier and can add tensio-active agent if necessary.
When preparation foliage spray preparation, for example wetting agent, spreader-sticker, dispersion agent, tackiness agent or thickening material improve result of use to need to add auxiliary agent usually.Auxiliary agent and using method commonly used all have description in many documents.For example " washing composition and emulsifying agent handbook.
In composition of the present invention, the weight percentage of active ingredient is between 0.1-99%.For the suitable weight percentage of the convenience of transporting and preserving between 0.5-90%, weight percentage preferably is between 1-75%.Composition also can compound and the ratio mode of carrier explain.
Common compound of the present invention can be dissolved in for example dilute with water again in acetone, methyl alcohol, ethanol, dimethyl formamide, pyridine or the dimethyl sulfoxide (DMSO) of specific solvent earlier, and its concentration can be 1% to 90% variation, and preferably is 5% to 50%.
Be the preparation emulsifiable concentrate, compound of the present invention is dissolvable in water a kind of or several mixed solvents, adds emulsifying agent again and strengthens the dispersion effect of compound in water.Active ingredient is usually between 10% to 90% in the emulsifiable concentrate.
Be the wettable powder that preparation is suitable for spraying, compound of the present invention can with pressed powder such as clay, inorganic silicate, carbonate and wetting agent, tackiness agent and or the dispersion agent composition mixture of porphyrize.Active ingredient is usually between 20% to 99%, and is preferably between 45% to 75%.For example typical 50% wettable powder is 50 parts of compounds of the present invention, 45 parts of silicate and 5 parts of sodium lignosulfonates.
The preparation of pulvis is the inert solid powder mixes by compound of the present invention and porphyrize.Suitable pressed powder such as plant powder, silicate, carbonate or clay.One easily method be with the dilution of the pressed powder of porphyrize with wettable powder.Active ingredient is generally between 20% to 80% in the pulvis, is diluted to 1% to 10% working concentration subsequently.
Compound of the present invention both can use separately also can be mixed together use with other known sterilant, sterilant, weedicide, plant-growth regulator or fertilizer etc.
Use for some, can in weedicide of the present invention, add one or more other weedicide, can produce additional advantage and effect thus.When using Herbicidal mixtures, employed relative proportion depends on the relative drug effect of this mixture to desire processing plant.When using the mixture of weedicide, employed relative quantity will depend on pending crop and the selectivity degree in the weed control of expection.Should be clear and definite be, can carry out various conversion and change under the situation of the scope of the invention defined by the claims.
Embodiment
Following synthetic embodiment, living survey embodiment and test-results form can be used to further specify the present invention, but do not mean that restriction is by the scope of the present invention shown in the claim.
Synthetic embodiment 1
Synthesizing of compound 1:
Step 1
In the reaction flask of 100ml, add A (7.1 grams 0.026mol) and the 70ml methylene dichloride, stir, add oxalyl chloride (5.0 grams, 0.039mol), 3 DMF, stirring at room 4 hours, concentrate 8.0 gram B1.
Step 2
(6.2 restrain, and 0.10mol), (1.2 restrain triethylamine to add ethylene glycol in the reaction flask of 100ml, 0.012mol) and 15ml methylene dichloride, stir cooling drip down B1 (2.9 grams, 0.01mol) and the mixed solution of 15ml methylene dichloride, add room temperature reaction 5 hours half an hour approximately.Add the 100ml ethyl acetate in reaction solution, organic phase is used 100ml water, saturated sodium bicarbonate solution, saturated common salt water washing respectively, anhydrous magnesium sulfate drying, concentrate 2.9 gram crude products.With developping agent is ethyl acetate: the silica gel column chromatography of sherwood oil=1: 2 separates, 1.3 gram C1.
Step 3
In the reaction flask of 500ml, add phenol (20 grams, 0.21mol), Mono Chloro Acetic Acid (20 grams, 0.21mol) and 100ml water, stir add down sodium hydroxide (17 grams, 0.43mol) and the solution of 100ml water, temperature rising reflux 6 hours.Reduce to room temperature, be acidified to pH=1, filter with concentrated hydrochloric acid, dry 12 gram white powder D1, MP:96-99 ℃.
The reaction flask of 100ml add D1 (12 grams 0.079mol) and the 50ml methylene dichloride, stir, add oxalyl chloride (20 grams, 0.16mol), 3 DMF, stirring at room 4 hours, reaction finishes, concentrate 15 gram E1.
Step 4
(0.7 restrains, and 0.0022mol), (0.34 restrains triethylamine to drop into C1 in the reaction flask of 50ml, 0.0033mol), methylene dichloride 10ml stirred 5 minutes, (0.5 gram, 0.0027mol) and the mixed solution of 10ml methylene dichloride, stirring at room is to reacting completely slowly to splash into phenoxyacetyl chloride El.Add the 50ml ethyl acetate in the mixed solution, organic phase is used 50ml water, saturated sodium bicarbonate solution, saturated common salt water washing respectively, anhydrous magnesium sulfate drying, concentrate 1.2 gram crude products.With developping agent is ethyl acetate: the silica gel column chromatography of sherwood oil=1: 4 separates, 1.0 digest compound 1.MP：68-78℃。
Synthetic embodiment 2
Synthesizing of compound 3:
In the reaction flask of 50ml, drop into A3 (0.5 gram, 0.0019mol, the same C1 of the preparation of A3), triethylamine (0.34 gram, 0.0025mol), methylene dichloride 10ml, stirred 5 minutes, slowly splash into B1 (0.66 gram, 0.0023mol) and the mixed solution of 10ml methylene dichloride, stirring at room is to reacting completely, in reaction solution, add the 50ml ethyl acetate, organic phase is used 50ml water, saturated sodium bicarbonate solution, saturated common salt water washing respectively, anhydrous magnesium sulfate drying, concentrate 0.84 gram crude product.With developping agent is ethyl acetate: the silica gel column chromatography of sherwood oil=1: 3 separates, 0.7 digest compound 3.MP：82-86℃。
Synthetic embodiment 3
Synthesizing of compound 6:
(0.32 restrains, and 0.0010mol), (0.14 restrains salt of wormwood to drop into C1 in the reaction flask of 50ml, 0.0010mol), methylene dichloride 15ml stirred 5 minutes, slowly splash into B6 (0.28 gram, 0.0010mol, the same E1 of the preparation of B6) and the mixed solution of 10ml methylene dichloride, be heated to and refluxed 8 hours, in reaction solution, add the 50ml ethyl acetate, organic phase is used 50ml water, saturated sodium bicarbonate solution, saturated common salt water washing respectively, anhydrous magnesium sulfate drying, concentrate 0.60 gram crude product.With developping agent is ethyl acetate: the silica gel column chromatography of sherwood oil=1: 3 separates, 0.40 gram half shape compound 6 admittedly.
Other compounds in the table 1 can make by above similar method.
Give birth to and survey embodiment
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.
Usually with the former medicine of acetone solution, or the preparation that makes by preceding method with water dissolution.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.
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 investigates in 2-3 week.With 1 (inhibiting rate 0-59%), 2 (60-69%), 3 (70-79%), 4 (80-89%), 5 (90--100%) carry out active classification.Inhibiting rate is total effect of various infringements such as chlorosis, withered spot, retarded growth or the calcination of leaf angle, with compare after obtain the result.Partial test the results are shown in Table 2.
Table 2: the weeding activity of compound in the part general formula I
[before the seedling behind (2250 gram/hectare)/seedling (2250 gram/hectare)]
| Compound | BYG | CRG | FOX | VEL | YOA |
| 1 | 5/4 | 5/5 | 5/5 | 5/5 | 5/5 |
| 6 | 5/5 | 5/5 | 5/5 | 5/5 | 5/5 |
| 9 | 5/5 | 5/5 | 1/2 | 5/5 | 5/5 |
| 11 | 5/5 | 5/4 | 5/4 | 5/5 | 5/5 |
| 13 | 5/5 | 5/5 | 5/5 | 5/5 | 5/5 |
| 14 | 5/5 | 5/5 | 5/5 | 5/5 | 5/5 |
| A | 1/1 | 5/1 | 5/1 | 5/5 | 5/5 |
Annotate 1: compd A is the compound in the English Patent (Brit.Patent 862226), is used for anti-broadleaf weeds.Its structural formula is as follows:
Table 3: weeds title
| Be called for short | Generic name | Latin name |
| BYG | The barnyard grass grass | Echinochloa crus-galli |
| CRB | Lady's-grass | Digitaria sanguinalis |
| FOX | The dog tail | Setaria viridis |
| VEL | Piemarker | Abutilon theophrasti |
| YOA | Youth-and-old-age | Zinnia elegans jacq |
Claims (7)
1. (4-chloro-2-oxygen-benzothiazole quinoline-3-yl) alkyl carboxylic ester compounds or its steric isomer with general formula (I) structure:
Wherein:
R
1, R
2Be H, (C
1-C
4) alkyl or halo (C
1-C
4) alkyl;
R
3, R
4Be H, halogen, CN, NO
2, (C
1-C
4) alkyl or halo (C
1-C
4) alkyl;
m＝2-10；
Q is H, halogen, CN, NO
2, (C
1-C
4) alkyl, halo (C
1-C
4) alkyl, Q1, Q2, Q3 or Q4:
R
5, R
6Be H, halogen, (C
1-C
4) alkyl or halo (C
1-C
4) alkyl;
R
7, R
8Be H, halogen, CN, NO
2, (C
1-C
4) alkyl or halo (C
1-C
4) alkyl;
R
9, R
10Be H, halogen, CN, NO
2, (C
1-C
4) alkyl or halo (C
1-C
4) alkyl;
X=O, N or S.
2. compound as claimed in claim 1 or its steric isomer is characterized in that:
R
1, R
2Be H or CH
3
R
3, R
4Be H, halogen, CN, (C
1-C
4) alkyl or halo (C
1-C
4) alkyl;
m＝2-6；
Q is H, halogen, and Q1, Q2, Q3 or Q4:
R
5, R
6Be H, halogen, (C
1-C
4) alkyl or halo (C
1-C
4) alkyl;
R
7, R
8Be H, halogen, CN or halo (C
1-C
4) alkyl;
R
9, R
10Be H or halogen;
X=O, N or S.
3. compound as claimed in claim 2 or its steric isomer is characterized in that:
R
1, R
2Be H or CH
3
R
3, R
4Be H, halogen, CN or methyl;
m＝2-4；
Q is H, halogen, Q1 or Q2
R
5, R
6Be H, halogen or methyl;
R
7, R
8Be H, halogen, CN, methyl or CF
3
4. compound as claimed in claim 3 or its steric isomer is characterized in that:
R
1, R
2Be H or CH
3
R
3, R
4Be H, halogen, CN or methyl;
m＝2-4；
Q is Q1
R
5, R
6Be H, halogen or methyl.
Among the claim 1-4 any described compound or its steric isomer as the purposes of weedicide.
6. herbicidal composition, it is characterized in that: said composition comprises any described compound or its steric isomer and acceptable carrier among the claim 1-4, and wherein the weight content of active ingredient is 0.1-99%.
7. control method for weed for one kind, it is characterized in that: this method comprises the herbicidal composition as claimed in claim 6 of using herbicidally effective amount on growth medium of these weeds or these weeds or place.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB011280778A CN1167693C (en) | 2001-08-23 | 2001-08-23 | Herbicidal (4-Cl-2-O-benzothiazolyline-3-group) alkyl carboxylic ester compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB011280778A CN1167693C (en) | 2001-08-23 | 2001-08-23 | Herbicidal (4-Cl-2-O-benzothiazolyline-3-group) alkyl carboxylic ester compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1406936A CN1406936A (en) | 2003-04-02 |
| CN1167693C true CN1167693C (en) | 2004-09-22 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB011280778A Expired - Fee Related CN1167693C (en) | 2001-08-23 | 2001-08-23 | Herbicidal (4-Cl-2-O-benzothiazolyline-3-group) alkyl carboxylic ester compounds |
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| Country | Link |
|---|---|
| CN (1) | CN1167693C (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7442673B2 (en) * | 2003-08-15 | 2008-10-28 | Crompton Corporation | Reaction products of mercaptobenzothiazoles, mercaptothiazolines, and mercaptobenzimidazoles with epoxides as lubricant additives |
| CN116554162A (en) * | 2022-12-30 | 2023-08-08 | 西北农林科技大学 | Benzothiazole compound and synthesis and application thereof |
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2001
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| Publication number | Publication date |
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| CN1406936A (en) | 2003-04-02 |
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