CN106831488A - A kind of 5- (3,4- di-substituted-phenyls)-hydroresorcinol class compound and its application - Google Patents
A kind of 5- (3,4- di-substituted-phenyls)-hydroresorcinol class compound and its application Download PDFInfo
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- CN106831488A CN106831488A CN201510886035.4A CN201510886035A CN106831488A CN 106831488 A CN106831488 A CN 106831488A CN 201510886035 A CN201510886035 A CN 201510886035A CN 106831488 A CN106831488 A CN 106831488A
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- 0 COc1c(*)ccc(C(C2)CC(O)=C(C(C*)=NOCC=C)C2=O)c1 Chemical compound COc1c(*)ccc(C(C2)CC(O)=C(C(C*)=NOCC=C)C2=O)c1 0.000 description 2
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
- C07C251/52—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by halogen atoms or by nitro or nitroso groups
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen
- A01N35/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen containing a carbon-to-nitrogen double bond
Abstract
The invention belongs to herbicide field.Specifically a kind of 5- (3,4- di-substituted-phenyls)-hydroresorcinol class compound and its application.Compound is as shown in logical formula (I)：Wherein：R1、R2It is respectively selected from methyl, ethyl, propyl group, isopropyl, methoxyl group, ethyoxyl, propoxyl group or isopropoxy；R3Selected from methyl, ethyl, propyl group or butyl.Compound of the invention not only has excellent activity of weeding, and to crop safety.
Description
Technical field
The invention belongs to herbicide field.Specifically a kind of 5- (3,4- di-substituted-phenyls)-hydroresorcinol class compound
And its application.
Background technology
Due to weed population succession, transition and it is drug-fast to chemical pesticide generation and develop rapidly, people are to ecology
The continuous reinforcement of environmental protection consciousness, on chemical pesticide pollution, the understanding that is influenceed on non-target organism of agricultural chemicals and in agricultural chemicals
The attention of home to return to problem is improved constantly in ecological environment.With the gradually decreasing of world's cultivated area, the continuous growth of population
And the increase to grain demand amount, force people to develop agriculture production technology, improvement rapidly and improve cropping system, and need
Constantly invent new and improved herbicides compounds and composition.
DE3329017A1 report some 1, hydroresorcinol class compound can be for example therein No. 123 as herbicide
Compound K C：
5- (3,4- di-substituted-phenyls)-hydroresorcinol class compound as representative of the present invention is not disclosed.
The content of the invention
It is an object of the invention to provide a kind of structure novelty and with 5- (3,4- the di-substituted-phenyls) -1,3- rings for activity of cutting weeds
Acetyl butyryl class compound and its application as herbicide.
To achieve the above object, technical scheme is as follows：
A kind of 5- (3,4- di-substituted-phenyl) -1, hydroresorcinol class compound, as shown in formula I：
In formula：
R1、R2It is respectively selected from methyl, ethyl, propyl group, isopropyl, methoxyl group, ethyoxyl, propoxyl group or isopropoxy；
R3Selected from methyl, ethyl, propyl group or butyl.
In currently preferred compound formula I：
R1、R2It is respectively selected from methoxyl group；
R3Selected from ethyl or propyl group.
In the compound formula I that the present invention is more highly preferred to：
R1、R2It is respectively selected from methoxyl group；
R3Selected from ethyl.
General formula compound I of the invention can be prepared by the following method：
Raw material II (can be bought by market) is dissolved in suitable solvent, and is added in alkaline aqueous solution, temperature is -10
DEG C reacted 0.5-48 hour between boiling point, prepared intermediate III.Suitable solvent be selected from acetone, chloroform, dichloromethane,
Carbon tetrachloride, n-hexane, benzene, toluene, ethyl acetate, methyl alcohol, ethanol, tetrahydrofuran or dioxane etc.；Suitably
Alkali be selected from NaOH, potassium hydroxide, sodium carbonate, potassium carbonate or sodium acid carbonate etc..
Diethyl malonate is dissolved in suitable solvent, alkaloids are added, stirring is started, temperature is arrived for -10 DEG C
Reacted 0.5-48 hours between boiling point, add intermediate III, continue to stir, temperature is -10 DEG C and is reacted between boiling point
0.5-48 hours, intermediate compound IV is obtained.Suitable solvent for example chloroform, dichloromethane, carbon tetrachloride, n-hexane, benzene,
Toluene, ethyl acetate, tetrahydrofuran, N,N-dimethylformamide or dioxane etc.；Alkaloids such as sodium methoxide, second
Sodium alkoxide, potassium tert-butoxide, NaOH, potassium hydroxide etc..
Intermediate compound IV is added to decarboxylation in concentrated hydrochloric acid, temperature is -10 DEG C and is reacted 0.5-48 hour between boiling point, makes
Obtain intermediate V.
Compound V is dissolved in suitable solvent, and adds alkali, acyl chlorides (R is slowly added dropwise under stirring3=CH3, it is second
Acyl chlorides；R3=CH2CH3, it is propionyl chloride；R3=CH2CH2CH3, be butyl chloride), temperature be -10 DEG C to boiling point it
Between react 0.5-48 hour, prepared enol ester intermediate.This intermediate is dissolved in the solvent of suitable intermediates, addition is urged
Agent, temperature is -10 DEG C to reaction 0.5-48 hours between boiling point, and intermediate VI is obtained.In suitable solvent, for example
Chloroform, dichloromethane, carbon tetrachloride, n-hexane, benzene, toluene, ethyl acetate, tetrahydrofuran or dioxane etc.；
Alkali such as triethylamine, NaOH, potassium hydroxide, sodium carbonate, potassium carbonate or sodium acid carbonate etc.；The solvent of suitable intermediates,
Such as chloroform, dichloromethane, carbon tetrachloride, acetonitrile, n-hexane, benzene, toluene, ethyl acetate, tetrahydrofuran, N, N-
Dimethylformamide or dioxane etc.；Catalyst such as DMAP or acetone cyanohydrin etc..
Intermediate VI is dissolved in suitable solvent, (E)-O- (3- chlorallyls) hydroxylamine hydrochloride is added, temperature is -10 DEG C
Reacted 0.5-48 hours between boiling point, object I is obtained；Suitable solvent for example methyl alcohol, ethanol, acetonitrile, chloroform,
Dichloromethane, carbon tetrachloride, n-hexane, benzene, toluene, ethyl acetate, tetrahydrofuran or dioxane etc..
Table 1：The compounds of this invention and physical property of the part as shown in formula I
Note：-- expression is not surveyed
Part of compounds1H NMR(300MHz,CDCl3) data are as follows：
Compound 2：14.26(s,1H),6.84–6.81(d,1H),6.77–6.72(m,2H),6.34–6.31(d,1H),
6.12–6.05(m,1H),4.53–4.50(d,2H),3.86–3.84(d,6H),3.32–3.24(m,1H),2.94-2.85(m,
2H),2.80-2.77(m,2H),2.72-2.56(m,2H),1.15-1.11(t,3H)。
Compound 3：14.35(s,1H),6.86–6.83(d,1H),6.80–6.74(m,2H),6.37–6.32(d,1H),
6.14–6.06(m,1H),4.54–4.52(d,2H),3.89–3.86(d,6H),3.34–3.26(m,1H),2.94-2.79(m,
4H),2.76-2.55(m,2H),1.59-1.53(q,2H),0.99-0.95(t,3H)。
Compound 5：14.34(s,1H),7.12–7.09(d,1H),6.76–6.68(m,2H),6.35–6.32(d,1H),
6.18–6.08(m,1H),4.56–4.52(d,2H),3.82(s,3H),3.38–3.28(m,1H),2.93-2.89(m,2H),
2.85-2.81(m,2H),2.79-2.60(m,2H),2.20(s,3H),1.18-1.13(t,3H)。
Compound 6：14.40(s,1H),7.12–7.09(d,1H),6.75–6.68(m,2H),6.34–6.31(d,1H),
6.14–6.10(m,1H),4.55–4.5(d,2H),3.83(s,3H),3.38–3.28(m,1H),2.93-2.88(m,2H),
2.85-2.81(m,2H),2.80-2.58(m,2H),2.20(s,3H),1.60-1.55(q,2H),1.00-0.95(t,3H)。
Compound 8：14.26(s,1H),7.04–7.01(m,2H),6.81–6.78(d,1H),6.37–6.32(d,1H),
6.13–6.10(m,1H),4.55–4.52(d,2H),3.82(s,3H),3.34–3.19(m,1H),2.93-2.89(m,2H),
2.80-2.77(m,2H),2.67-2.58(m,2H),2.22(s,3H),1.18-1.13(t,3H)。
Compound 9：14.26(s,1H),7.03–7.00(m,2H),6.80–6.77(d,1H),6.36–6.32(d,1H),
6.13–6.06(m,1H),4.53–4.51(d,2H),3.81(s,3H),3.30–3.21(m,1H),2.93-2.88(m,2H),
2.80-2.77(m,2H),2.67-2.58(m,2H),2.21(s,3H),1.59-1.53(q,2H),0.99-0.95(t,3H)。
Compound of Formula I of the invention has activity of weeding, can be used to agriculturally prevent and treat various weeds.With prior art institute
Disclosed compound phase ratio, 5- (3,4- di-substituted-phenyl) -1 of the invention, hydroresorcinol class compound not only has excellent
Activity of weeding, and to crop safety.
Present invention additionally comprises the Herbicidal combinations with compound of Formula I as active component.Active component in the Herbicidal combinations
Weight percentage be 1-99%.Also include agriculturally acceptable carrier in the Herbicidal combinations.
Herbicidal combinations of the invention can be applied in the form of several formulations.Generally compound of the invention is dissolved or disperseed
It is more readily dispersible when being configured to preparation to be used as herbicide in carrier.For example：These chemicals can be made into
Wettable powder or missible oil etc..Therefore, in these compositions, a kind of liquid or solid carrier is at least added, and lead to
Often need to add appropriate surfactant.
Present invention also offers the implementation of controlling weeds, the method is included the weeding group of the invention of herbicidally effective amount
Compound is imposed on the weeds or the place of the weed growth or the surface of its somatomedin.More suitable effective dose is
1 gram to 1000 grams of per hectare, preferably effective dose are 10 grams to 500 grams of per hectare.For some applications, can be at this
One or more other herbicide is added in the Herbicidal combinations of invention, additional advantage and effect thus can be produced.
Compound of the invention both can be used alone can also be adjusted with other known insecticide, bactericide, plant growth
Section agent or fertilizer etc. are mixed together.
It should be appreciated that, in scope defined by the claims of the present invention, various conversion and change can be carried out.
Specific embodiment
The following example and raw test result can be used to further illustrate the present invention, but be not intended to limit the present invention.
Synthesis example
The synthesis of embodiment 1, compound 2：
(1) synthesis of intermediate 4- (3,4- Dimethoxyphenyls)-3- butene-2 -one
To Veratraldehyde (15.50 grams, 93 mMs) is added in the reaction bulb of 1L, acetone 150 is added
Milliliter and 300 milliliters of water, are added dropwise 5% 75 milliliters of sodium hydrate aqueous solution under ice bath, completion of dropping keeps room temperature,
Continue to stir 8 hours, TLC detections, raw material reaction is complete.Add methylene chloride extraction (150 milliliters × 3), dichloromethane
Layer washing (250 milliliters × 3), saturated common salt washing (250 milliliters) is dried, and solvent evaporated obtains yellow fluid 15.27
Gram.
(2) synthesis of intermediate 5- (3,4- Dimethoxyphenyls) -3- hydroxyl -2- cyclohexene -1- ketone
To caustic alcohol (9.00 grams, 132 mMs) and 50 milliliters of ethanol is added in 250 milliliters of reaction bulbs, the third two are added
Diethyl phthalate (17.76 grams, 111 mMs), hot add-back stream 1 hour.Reaction solution is cooled to 40 DEG C, 50 millis are added
Ethanol and 4- (3,4- Dimethoxyphenyl) -3- butene-2s -one (15.27 grams, 74 mMs) are risen, 60 DEG C, insulation are heated to
Reaction 2 hours.Gradually there is the solid insoluble in ethanol to separate out in course of reaction.After reaction terminates, decompression steams ethanol,
Obtain brown fluid.
To 80 milliliters of the sodium hydrate aqueous solution for Jia 7% in reaction bulb, after being heated to reflux 6 hours, room temperature is down to, used
Ethyl acetate washs (30 milliliters × 2), separates water layer standby.Water layer enriching hydrochloric acid (30.65 grams, 294 mMs), heating
To flowing back, gradually there is solid to separate out in settled solution, after stirring 6 hours, raw material reaction is complete.Filtering, dries, and obtains
8.65 grams of yellow solid product.
(3) synthesis of intermediate 5- (3,4- Dimethoxyphenyls) -2- propionos -3- hydroxyl -2- cyclohexene -1- ketone
To added in 100 milliliters of reaction bulbs 5- (3,4- Dimethoxyphenyl) -3- hydroxyl -2- cyclohexene -1- ketone (1.15 grams,
4.43 mMs) and 40 milliliters of dichloromethane, after adding triethylamine (0.50 gram, 4.94 mMs), solid is gradually
Dissolving, is added dropwise propionyl chloride (0.44 gram, 4.76 mMs) under ice bath, after room temperature continues to stir 2 hours, put plate, former
Material reaction is complete.Extraction, organic phase is respectively with watery hydrochloric acid (1 mol/L, 40 milliliters), dilute sodium hydroxide aqueous solution (1
Mol/L, 40 milliliters) and (40 milliliters) washings of water, organic layer drying, depressurize and steam solvent, obtain yellow fluid.
The yellow fluid that will be obtained is dissolved in 20 milliliters of toluene, adds DMAP (0.25 gram, 2.046 mMs),
It is refluxed reaction 2 hours.TLC display reactions are complete.Evaporated under reduced pressure toluene, adds 50 milliliters of water and 50 milliliter two
Chloromethanes, adds 2 milliliters of concentrated hydrochloric acids, and vibration discards water layer.Organic layer water (40 milliliters) is washed, saturated aqueous common salt (40
Milliliter) washing, dry, it is spin-dried for obtaining brown fluid.Column chromatography for separation product, obtains 0.62 gram of yellow solid.
(3) synthesis of compound 2
To addition 5- (3,4- Dimethoxyphenyls) -2- propiono -3- hydroxyl -2- cyclohexene -1- ketone in 100 milliliters of reaction bulbs
(0.62 gram, 2.037 mMs) and (E)-O- (3- chlorallyls) hydroxylamine hydrochloride (0.30 gram, 2.083 mMs),
20 milliliters of ethanol are added, triethylamine (0.25 gram, 2.471 mMs) is finally slowly added dropwise, stirs anti-at 25 DEG C
Should, plate is put after 8 hours, reaction is complete.Decompression steams ethanol, and silica gel mixed sample crosses post, pillar layer separation (petroleum ether：
Ethyl acetate=10:1) 0.71 gram of faint yellow solid product, purity 90%, are obtained.
The synthesis of embodiment 2, compound 3：
(1) synthesis of intermediate 5- (3,4- Dimethoxyphenyls) -2- bytyries -3- hydroxyl -2- cyclohexene -1- ketone
To added in 100 milliliters of reaction bulbs 5- (3,4- Dimethoxyphenyl) -3- hydroxyl -2- cyclohexene -1- ketone (1.00 grams,
4.03 mMs) and 40 milliliters of dichloromethane, after adding triethylamine (0.45 gram, 4.44 mMs), solid by
Gradually dissolve, butyl chloride (0.43 gram, 4.04 mMs) be added dropwise under ice bath, after room temperature continues to stir 2 hours, put plate,
Raw material reaction is complete.Extraction, respectively with watery hydrochloric acid, dilute sodium hydroxide aqueous solution and washing, organic layer is dried organic phase,
Decompression steams solvent, obtains yellow fluid.
The yellow fluid that will be obtained is dissolved in 20 milliliters of toluene, adds DMAP (0.25 gram, 2.046 mMs),
It is refluxed reaction 2 hours.TLC display reactions are complete.Evaporated under reduced pressure toluene, adds 50 milliliters of water and 50 milliliter two
Chloromethanes, adds 2 milliliters of concentrated hydrochloric acids, and vibration discards water layer.Organic layer water (40 milliliters) is washed, saturated aqueous common salt (40
Milliliter) washing, dry, it is spin-dried for obtaining brown fluid.Column chromatography for separation product, obtains 0.72 gram of yellow solid.
(2) synthesis of compound 3
To addition 5- (3,4- Dimethoxyphenyls) -2- bytyry -3- hydroxyl -2- cyclohexene -1- ketone in 100 milliliters of reaction bulbs
(0.40 gram, 1.256 mMs) and (E)-O- (3- chlorallyls) hydroxylamine hydrochloride (0.19 gram, 1.319 mMs),
20 milliliters of ethanol are added, triethylamine (0.15 gram, 1.482 mMs) is finally slowly added dropwise, stirs anti-at 25 DEG C
Should, plate is put after 8 hours, reaction is complete.Decompression steams ethanol, and silica gel mixed sample crosses post, pillar layer separation (petroleum ether：
Ethyl acetate=10:1) 0.29 gram of faint yellow solid product, purity 90%, are obtained.
Other compounds in table 1 can be obtained by the method similar with above example.
It is raw to survey example
After active compound acetone solution, the to be measured of concentration needed for running water is prepared is stood with 1 ‰ Tween 80 by test requirements document
Liquid.Spraying treatment (spraying pressure is carried out with crawler type crops sprayer (Britain Engineer Research Ltd. design production)
Power 1.95kg/cm2, spouting liquid 50mL/m2, crawler track speeds 30cm/s, nozzle is fan nozzle).
Prevent and kill off barnyard grass activity test：Quantitative barnyard grass seed is sowed in the culturing pot that sectional area is 100cm2, is covered after broadcasting
Native 1cm, cultivates according to a conventional method after suppression, water drenching in greenhouse.Treat that weeds are long to 1.5 leaf phases, choose growth uniform
The examination material of cause carries out after seedling cauline leaf spraying treatment, and water treatment as control is stood using 1 ‰ Tween 80.Examination material treatment
After be placed in handling hall, after after liquid natural air drying, be placed in greenhouse and manage according to a conventional method, after treatment in 48 hours
Method using being poured water from bottom, it is to avoid liquid is washed.21 days range estimation investigation test compounds are to barnyard grass after treatment
Preventive effect.
Compound of Formula I has carried out, except the barnyard grass parallel contrast test of activity, the results are shown in Table 2 with known compound KC.
Table 2：The compounds of this invention prevents and kill off barnyard grass activity with compound KC's
(after seedling, preventive effect %)
Note：KC is No. 123 compounds in DE3329017A1 patents.The application carries out sample with reference to method in DE3329017A1 patents
It is prepared by product.The physical property of KC is shown in Table 3.
Table 3：The physical property of KC：
Security of rice is tested：Quantitative rice paddy seed is sowed at sectional area for 100cm2Culturing pot in, broadcast rear earthing
1cm, cultivates according to a conventional method after suppression, water drenching in greenhouse.Treat that paddy rice is long to 3 leaf phases, choose growth uniformity
Examination material carries out after seedling cauline leaf spraying treatment, and water treatment as control is stood using 1 ‰ Tween 80.Put after examination material treatment
Ventilation is being dried, after after liquid natural air drying, is being placed in greenhouse and is managed according to a conventional method, adopted in 48 hours after treatment
Method with being poured water from bottom, it is to avoid liquid is washed.Carry out within 4 weeks after treatment range estimation investigation, inhibiting rate be with to photograph
The various degree of injury of ratio, including kill, chlorosis, withered spot, distortion, deformity, growth inhibition or blade calcination etc..
Safe to wheat is tested：Quantitative wheat seed is sowed in the dixie cup equipped with Nutrition Soil of a diameter of 7cm, is broadcast
Earthing 1cm, cultivates according to a conventional method after suppression, water drenching in greenhouse afterwards.Treat that wheat is long to 3 leaf phases, choose growth uniform
Consistent examination timber-used crawler type crops sprayer (Britain Engineer Research Ltd. designs production) is carried out at cauline leaf spraying
Reason (atomisation pressure 1.95kg/cm2, spouting liquid 50mL/m2, crawler track speeds 30cm/s, nozzle is fan nozzle),
Handling hall is placed in after examination material treatment, after after liquid natural air drying, is placed in greenhouse and is managed according to a conventional method.It is fixed after treatment
Phase observes wheat to the response situation of test compound, carries out range estimation investigation in 4 weeks after treatment, inhibiting rate be with to photograph
The various degree of injury of ratio, including kill, chlorosis, withered spot, distortion, deformity, growth inhibition or blade calcination etc..
Compound of Formula I has security high to crop after seedling, and for example compound 2 is in 37.5g a.i./hm2Under dosage,
Poisoning to paddy rice and wheat is 0.
Claims (6)
1. a kind of 5- (3,4- di-substituted-phenyl) -1, hydroresorcinol class compound, it is characterised in that：Compound is such as
Shown in formula I：
In formula：
R1、R2Be respectively selected from methyl, ethyl, propyl group, isopropyl, methoxyl group, ethyoxyl, propoxyl group or
Isopropoxy；
R3Selected from methyl, ethyl, propyl group or butyl.
2. compound as claimed in claim 1, it is characterised in that in formula I：
R1、R2It is respectively selected from methoxyl group；
R3Selected from ethyl or propyl group.
3. compound as claimed in claim 2, it is characterised in that in formula I：
R1、R2It is respectively selected from methoxyl group；
R3Selected from ethyl.
4. the compound described in a kind of claim 1 is used to control the application of weeds.
5. a kind of Herbicidal combinations, it is characterised in that：Contain compound of Formula I as claimed in claim 1
Agriculturally acceptable carrier, the weight percentage of active component is 1-99% in composition.
6. a kind of Herbicidal combinations as claimed in claim 5 control weeds method, it is characterised in that：
To on the somatomedin or place of weeds or weeds using weeding effective dose claim 5 described in weeding
Composition.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111094245A (en) * | 2017-09-11 | 2020-05-01 | 山东先达农化股份有限公司 | Compound containing fluoropyridine chloride oxime ester structure, preparation method and application thereof, and herbicide |
| CN112142671A (en) * | 2019-06-27 | 2020-12-29 | 东莞市东阳光农药研发有限公司 | Substituted benzoyl-pyrazole compounds and application thereof in agriculture |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4652303A (en) * | 1983-07-18 | 1987-03-24 | Ici Australia Limited | Herbicidal 5-(acylphenyl)cyclohexane-1,3-dione derivatives |
| EP0266068A1 (en) * | 1986-10-14 | 1988-05-04 | Imperial Chemical Industries Plc | Herbicidal composition |
| US4760192A (en) * | 1981-11-20 | 1988-07-26 | Imperial Chemical Industries Plc | Herbicidal cyclohexane-1,3-dione derivatives |
| US4898610A (en) * | 1983-08-11 | 1990-02-06 | Basf Aktiengesellschaft | Cyclohexane-1,3-dione derivatives and their use for controlling undesirable plant growth |
| EP0450711A1 (en) * | 1990-03-30 | 1991-10-09 | Dowelanco | Substituted cyclohexanediones and their herbicidal uses |
-
2015
- 2015-12-04 CN CN201510886035.4A patent/CN106831488B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4760192A (en) * | 1981-11-20 | 1988-07-26 | Imperial Chemical Industries Plc | Herbicidal cyclohexane-1,3-dione derivatives |
| US4652303A (en) * | 1983-07-18 | 1987-03-24 | Ici Australia Limited | Herbicidal 5-(acylphenyl)cyclohexane-1,3-dione derivatives |
| US4898610A (en) * | 1983-08-11 | 1990-02-06 | Basf Aktiengesellschaft | Cyclohexane-1,3-dione derivatives and their use for controlling undesirable plant growth |
| EP0266068A1 (en) * | 1986-10-14 | 1988-05-04 | Imperial Chemical Industries Plc | Herbicidal composition |
| EP0450711A1 (en) * | 1990-03-30 | 1991-10-09 | Dowelanco | Substituted cyclohexanediones and their herbicidal uses |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111094245A (en) * | 2017-09-11 | 2020-05-01 | 山东先达农化股份有限公司 | Compound containing fluoropyridine chloride oxime ester structure, preparation method and application thereof, and herbicide |
| CN111094245B (en) * | 2017-09-11 | 2023-01-03 | 山东先达农化股份有限公司 | Compound containing fluoropyridine chloride oxime ester structure, preparation method and application thereof, and herbicide |
| CN112142671A (en) * | 2019-06-27 | 2020-12-29 | 东莞市东阳光农药研发有限公司 | Substituted benzoyl-pyrazole compounds and application thereof in agriculture |
| CN112142671B (en) * | 2019-06-27 | 2024-01-16 | 东莞市东阳光农药研发有限公司 | Substituted benzoyl-pyrazoles and application thereof in agriculture |
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