CN1128146C - Dibenzo-1,3-dioxo-cyclooctane-2-oximino carboxylate compound with herbicidal activity - Google Patents
Dibenzo-1,3-dioxo-cyclooctane-2-oximino carboxylate compound with herbicidal activity Download PDFInfo
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- CN1128146C CN1128146C CN 00110733 CN00110733A CN1128146C CN 1128146 C CN1128146 C CN 1128146C CN 00110733 CN00110733 CN 00110733 CN 00110733 A CN00110733 A CN 00110733A CN 1128146 C CN1128146 C CN 1128146C
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- alkyl
- compound
- cyclooctane
- dioxo
- dibenzo
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Abstract
The present invention relates to a dibenzo-1, 3-dioxo-cyclooctane-2-oximin carboxylate compound with herbicidal activity and a composition thereof, which comprises a general formula: an I formula, wherein the R1 is H, halogen and alkyl; the R2 and the R3 are H, halogen, CN, NO2, alkyl, etc.; the R4 and the R5 are H, halogen and alkyl or can form rings, such as-CH2CH2-,-CH2CH2CH2-, etc.; the R6 and the R7 are H, halogen CN, NO2, alkyl, alkyl carbonyl, carbalkoxy, aryl, etc. or can form (C3-C10) rings. The m is equal to 1 to 3, and the n is equal to 1 to 3.
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 dibenzo-1,3-dioxo-cyclooctane-2-carboxylic acid ester compound are as medicine (J.Medicinal Chemistry, 15,1273-1278 (1972)), and weedicide (US4938790 and US4976770) is existing to be reported.But in above-mentioned patent, do not see open as oxime ester compound shown in the present.
Summary of the invention
The invention provides a kind of new dibenzo-1,3-dioxo-cyclooctane-2-oximino carboxylate compound, its composition, acceptable carrier, as broad-spectrum herbicide, behind Miao Qianmiao, use and can effectively control single broadleaf weed, especially perennial weeds there be tall and erect the effect.The present invention also relates to these compounds of preparation, uses the method that these compounds carry out weeding.
(I) is as follows for the general formula of compound provided by the present invention:
Wherein:
R
1Be H, halogen, (C
1-C
4) alkyl, halo (C
1-C
4) alkyl;
R
2, R
3Be H, halogen, CN, NO
2, CO
2H, NH
2, (C
1-C
4) alkyl, halo (C
1-C
4) alkyl, (C
1-C
4) alkoxyl group, phenoxy group, (C
1-C
4) alkylthio, (C
1-C
3) alkyl-carbonyl, (C
1-C
3) carbalkoxy, (C
1-C
4) dialkyl amido, (C
1-C
4) alkyl sulphonyl;
R
4, R
5Be H, halogen, (C
1-C
4) alkyl, halo (C
1-C
5) alkyl; Or R
4, R
5Can form ring, as-CH
2CH
2-,-CH
2CH
2CH
2-;
R
6Be H, halogen, CN, NO
2, (C
1-C
10) alkyl, halo (C
1-C
10) alkyl, (C
3-C
10) cycloalkyl, (C
2-C
6) thiazolinyl, (C
3-C
6) alkynyl, (C
1-C
10) alkoxyl group, phenoxy group, (C
1-C
10) alkylthio, (C
1-C
8) alkyl-carbonyl,
(C
1-C
8) carbalkoxy, (C
1-C
8) dialkyl amino carbonyl, aryl;
R
7Be halogen, CN, NO
2, (C
1-C
10) alkyl, halo (C
1-C
10) alkyl, (C
3-C
10) cycloalkyl, (C
2-C
6) thiazolinyl, (C
3-C
6) alkynyl, (C
1-C
10) alkoxyl group, phenoxy group, (C
1-C
10) alkylthio, (C
1-C
8) alkyl-carbonyl, (C
1-C
8) carbalkoxy, (C
1-C
8) dialkyl amino carbonyl, aryl;
Or R
6, R
7Can form (C
3-C
10) unit's ring;
m＝1-3；n＝1-3。
Comparatively preferred compound is among the present invention: in the general formula (I)
R
1, R
2, R
3Be H or (C
1-C
4) alkyl;
R
4, R
5Be H, (C
1-C
4) alkyl or R
4With R
5Form C
3Or C
4Unit's ring;
R
6Be H or (C
1-C
6) alkyl;
R
7Be (C
1-C
8) alkyl, (C
1-C
4) alkyl-carbonyl or phenyl;
Or R
6With R
7Form (C
3-C
7) unit's ring.
More preferred compound is among the present invention: in the general formula (I)
R
1, R
2, R
3Be H;
R
4, R
5Be H, or R
4With R
5Be together-CH
2CH
2-;
R
6Be H or (C
1-C
4) alkyl;
R
7Be (C
1-C
5) alkyl, methyl carbonyl or phenyl;
Or R
6With R
7Be together-(CH
2)
5-.
Further preferred compound is among the present invention: in the general formula (I)
R
1, R
2, R
3, R
4, R
5Be H;
R
6, R
7Be CH
3
So-called alkyl is meant the straight or branched form, for example groups such as methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, isobutyl-, sec-butyl, tertiary butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, positive decyl.Cycloalkyl is meant and comprises the closed chain form, for example groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, suberyl, ring octyl group.Alkylhalide group is meant the group that alkyl is replaced by one or more halogen atoms.
So-called 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.
So-called 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.
So-called alkoxyl group is meant the straight or branched form, and end is connected with the group of Sauerstoffatom, for example methoxyl group, oxyethyl group, positive propoxy, isopropoxy, tert-butoxy etc.
So-called aryl is meant phenyl ring, fragrant heterocycle such as pyridine, pyrimidine etc.
So-called alkylthio is meant the straight or branched form, and end is connected with the group of sulphur atom, for example methylthio group, ethylmercapto group etc.
So-called halogen is meant fluorine, chlorine, bromine, iodine.
General formula compound of the present invention (I) can be prepared by following method:
Acyl chlorides (II) and oxime (can by buying on the market or can being made by currently known methods, referring to EPA0658549A1) be in The suitable solvent, and temperature is reacted down to boiling point and to be made compound (I) in 0.5-48 hour for-10 ℃.Solvent can be chloroform, methylene dichloride, tetracol phenixin, hexane, benzene, toluene, ethyl acetate, 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.
Acid (III) 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 compound (II) for-10 ℃ in 0.5-48 hour to the following reaction of boiling point.
Fortified phenol [can be by buying on the market or can being made by currently known methods, referring to J.Org.Chem.USSR (Engl.Transl.), 11,1985,2403-2407] and α, α-dihalo carboxylic acid or its ester are dissolved in the The suitable solvent, chloroform for example, methylene dichloride, tetracol phenixin, normal hexane, benzene, toluene, ethyl acetate, DMF, THF, dioxane, 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) 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) in reaction 0.5-24 such as alcohol hour in the The suitable solvent.
The The compounds of this invention of table 1 part shown in general formula I
Compound R
4R
5R
6R
7Mp (℃) 1 H H CH
3CH
3144-1462 H H CH
3CH
3CH
2-92-933 H H CH
3N-C
5H
11-oily * 4 H H CH
3(CH
3)
3C-oil * * 5 H H (CH3)
3C-(CH
3)
3C-104-1076 H H-(CH
2)
5-oily * * * 7 H H H phenyl oil * * * * 8-(CH
2CH
2)-CH
3CH
3Oil * * * * * 9 H H CH
3CH
3CO-108-111
*：
1H NMR(CDCl
3)：7.35(m，2H)，7.10(m，6H)，5.22(s，1H)，4.65(dd，1H)，3.52(dd，1H)，2.44(t，2H)，2.21(m，2H)，2.11(s，3H)，1.72(m，2H)，1.38(br，3H).
**：
1H NMR(CDCl
3)：7.36(m，2H)， 7.12(m，6H)，5.22(s，1H)，4.65(dd，1H)，3.50(dd，1H)，2.09(s，3H)，1.27(s，9H).
***：
1H NMR(CDCl
3)：7.35(m，2H)，7.10(m，6H)，5.21(s，1H)，4.65(dd，1H)，3.51(dd，1H)，2.67(m，2H)，2.47(m，2H)，1.80(m，6H).
****：
1H NMR(CDCl
3)：8.60(s，1H)，7.80(m，2H)，7.5-7.0(m，11H)，5.30(s，1H)，4.65(dd，1H)，3.54(dd，1H).
*****：
1H NMR(CDCl
3)：7.33(m，2H)，7.06(m，6H)，5.42(s，1H)，2.11(s，6H)，1.25(m，4H).
The present invention also comprises by a certain dibenzo of being made up of the compound and the carrier of weeding activity-1 shown in the general formula (I), 3-dioxo-cyclooctane-2-oximino carboxylate compound herbicidal composition.
Other embodiments of the present invention are method of controlling weeds, this method comprises the dibenzo-1 that compound shown in the general formula of herbicidally effective amount (I) and acceptable carrier are formed, and 3-dioxo-cyclooctane-2-oximino carboxylate herbicidal composition imposes on the surface of growth medium of the places of described weeds or described weeds or described weeds.
Dibenzo of the present invention-1,3-dioxo-cyclooctane-2-oximino carboxylate compound 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..
Dibenzo of the present invention-1,3-dioxo-cyclooctane-2-oximino carboxylate compound 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 10 restrains 3000 grams, and preferred significant quantity is that per hectare 50 restrains 1000 grams.
Dibenzo of the present invention-1,3-dioxo-cyclooctane-2-oximino carboxylate compound herbicidal composition can mix with fertilizer before using mutually.Used said dibenzo-1 in a class, in the solid fertilizer composition of 3-dioxo-cyclooctane-2-oximino carboxylate compound, 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 general said dibenzo-1, the 3-dioxo-cyclooctane-ratio of 2-oximino carboxylate compound 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.Preparation preparation or method for compositions can be with reference to " pesticide preparation research " (the publishing in 1969) or the chemical progress seriess of books " pesticide preparation " (publishing in 1973) of American Chemical Society's publication.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, tamanori 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, tamanori 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
The following example, give birth to that the result is tested in test and 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
The preparation of compound 8 in the table 1:
Under the ice-water bath condition, oxalyl chloride (0.2g) joined acid (III-1) (0.2g) and CH
2Cl
2In the mixture (10ml), drip a DMF then.After reaction mixture at room temperature stirs and spends the night, obtain partly target compound (II-1) 0.2g of shape admittedly except that desolvating by underpressure distillation.
Under the ice-water bath condition will on go on foot product (II-1) and (0.2g) join the CH of oxime (0.1g) and triethylamine (0.2g)
2Cl
2(10ml) in the solution.Reaction soln at room temperature stirred 3 hours, evaporate to dryness, and residuum extracts with ethyl acetate (100ml), and organic layer is water, 1%NaHCO successively
3Use anhydrous MgSO after the aqueous solution and the saturated common salt water washing
4Dry.Obtain buttery target compound (I-1) 0.15g after the underpressure distillation.
1H NMR(CDCl
3)：7.33(m，2H)，7.06(m，6H)，5.42(s，1H)，2.11(s，6H)，1.25(m，4H)。
Other compound in the table 1 all 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.Carry out active classification with 0% (invalid) to 100% (control fully).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 (1200 gram/hectare)/seedling (1200 gram/hectare)]
| Compound | BID | NS | SMT | VEL | BYG | CRB | FOX | NUT | RYE |
| 1 | 95/100 | 85/95 | 85/85 | 30/80 | 90/85 | 0/0 | 30/85 | 95/90 | 100/90 |
| 2 | 90/100 | 80/100 | 80/80 | 80/70 | 90/70 | 0/0 | 40/80 | 100/95 | 100/85 |
| 3 | 95/95 | 80/95 | 80/40 | 40/40 | 80/80 | 0/0 | 0/80 | 100/80 | 95/70 |
| 4 | 95/95 | 80/95 | 85/60 | 40/70 | 90/80 | 0/0 | 40/70 | 95/90 | 100/70 |
| 5 | 100/95 | 80/95 | 60/80 | 40/90 | 90/80 | 0/0 | 70/80 | 100/90 | 100/70 |
| 6 | 90/90 | 80/90 | 80/60 | 40/40 | 60/60 | 0/0 | 0/80 | 100/70 | 100/80 |
| 7 | 95/90 | 80/95 | 80/40 | 60/60 | 80/70 | 0/0 | 40/70 | 100/70 | 100/70 |
| 8* | -/100 | -/100 | -/40 | -/95 | -/85 | -/0 | -/90 | -/90 | -/95 |
| 9** | 90/100 | 80/90 | 60/85 | 0/80 | 80/80 | 0/0 | 60/70 | 100/90 | 80/60 |
*: test is not surveyed before the seedling, and test dose is 600 gram/hectares behind the seedling.
*: test dose is 600 gram/hectares before the seedling and behind the seedling.
Table 3: weeds title
| Be called for short | Generic name | Latin name |
| BID | Herba Bidentis Bipinnatae | Bidens pilosa |
| NS | Black nightshade (deceiving) | Solanum nigrum |
| SMT | Few | Polygonum lapathifolium |
| VEL | Piemarker | Abutilon theophrasti |
| BYG | The barnyard grass grass | Echinochloa crus-galli |
| CRB | Lady's-grass (greatly) | Digitaria sanguinalis |
| FOX | Green dog tail | Setaria viridis |
| NUT | Nutgrass flatsedge (Huang) | Cyperus esculentus |
| RYE | Rye grass | Lolium perenne |
Claims (6)
1. dibenzo-1 with weeding activity, 3-dioxo-cyclooctane-2-oximino carboxylate compound is characterized in that the general formula of this compounds is:
Wherein:
R
1, R
2, R
3Be H or (C
1-C
4) alkyl;
R
4, R
5Be H, (C
1-C
4) alkyl or R
4With R
5Form C
3Or C
4Unit's ring;
R
6Be H or (C
1-C
6) alkyl;
R
7Be (C
1-C
8) alkyl, (C
1-C
4) alkyl-carbonyl or phenyl;
Or R
6With R
7Form (C
3-C
7) unit's ring;
m＝1-3；
n＝1-3。
2. compound as claimed in claim 1 is characterized in that:
R wherein
1, R
2, R
3Be H;
R
4, R
5Be H, or R
4With R
5Be together-CH
2CH
2-;
R
6Be H or (C
1-C
4) alkyl;
R
7Be (C
1-C
5) alkyl, methyl carbonyl or phenyl;
Or R
6With R
7Be together-(CH
2)
5-.
3. compound as claimed in claim 2 is characterized in that:
R wherein
1, R
2, R
3, R
4, R
5Be H;
R
6, R
7Be CH
3
4. herbicidal composition, it is characterized in that: said composition comprises described compound of claim 1 and acceptable carrier thereof, wherein the weight content of active ingredient is 0.1-99%.
5. control method for weed for one kind, it is characterized in that: this method comprises the herbicidal composition as claimed in claim 4 of using herbicidally effective amount on growth medium of these weeds or these weeds or place.
6. claim 1 described dibenzo-1,3-dioxo-cyclooctane-2-oximino carboxylate compound and composition thereof can effectively be controlled the purposes of single broadleaf weed and perennial weeds as broad-spectrum herbicide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 00110733 CN1128146C (en) | 2000-07-27 | 2000-07-27 | Dibenzo-1,3-dioxo-cyclooctane-2-oximino carboxylate compound with herbicidal activity |
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|---|---|
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| CN1128146C true CN1128146C (en) | 2003-11-19 |
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ID=4580711
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