CN106831488B - 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
- Publication number
- CN106831488B CN106831488B CN201510886035.4A CN201510886035A CN106831488B CN 106831488 B CN106831488 B CN 106831488B CN 201510886035 A CN201510886035 A CN 201510886035A CN 106831488 B CN106831488 B CN 106831488B
- Authority
- CN
- China
- Prior art keywords
- compound
- milliliters
- added
- substituted
- gram
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Classifications
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention belongs to herbicide fields.Specifically a kind of 5 (3,4 di-substituted-phenyl) 1,3 benzoylcyclohexandiones and its application.Compound is as shown in logical formula (I)：Wherein：R1、R2It is respectively selected from methyl, ethyl, propyl, isopropyl, methoxyl group, ethyoxyl, propoxyl group or isopropoxy；R3Selected from methyl, ethyl, propyl or butyl.The compound of the present invention not only has excellent activity of weeding, and to crop safety.
Description
Technical field
The invention belongs to herbicide fields.Specifically a kind of 5- (3,4- di-substituted-phenyls)-hydroresorcinol class
Compound and its application.
Background technology
Due to the succession of weed population, transition and generation and rapid development to chemical pesticide drug resistance, people are to life
The continuous reinforcement of state environmental protection consciousness, the understanding that non-target organism is influenced on chemical pesticide pollution, pesticide and in pesticide
The attention of home to return to problem is continuously improved in ecological environment.With the gradually decreasing of world's cultivated area, population continuous growth and
Increase to grain demand amount forces people to rapidly develop agriculture production technology, improves and improve cropping system, and needs constantly hair
Bright novel and improved herbicides compounds and composition.
DE3329017A1 reports certain 1, and hydroresorcinol class compound can be used as herbicide, such as No. 123 therein
Compound K C：
5- (3,4- di-substituted-phenyls)-hydroresorcinol class compound as representative of the present invention is not disclosed.
Invention content
The object of the present invention is to provide a kind of structure novel and there is the active 5- (3,4- di-substituted-phenyls) -1 that cuts weeds,
Hydroresorcinol 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 general formula I：
In formula：
R1、R2It is respectively selected from methyl, ethyl, propyl, isopropyl, methoxyl group, ethyoxyl, propoxyl group or isopropoxy；
R3Selected from methyl, ethyl, propyl or butyl.
In currently preferred compound formula I：
R1、R2It is respectively selected from methoxyl group；
R3Selected from ethyl or propyl.
In the present invention more preferably compound formula I：
R1、R2It is respectively selected from methoxyl group；
R3Selected from ethyl.
The general formula compound I of the present invention can be prepared by the following method：
Raw material II (being available on the market) is dissolved in suitable solvent, and is added in alkaline aqueous solution, temperature is -10
It DEG C is reacted 0.5-48 hours between boiling point, intermediate III is made.Suitable solvent is selected from acetone, chloroform, dichloromethane, tetrachloro
Change carbon, n-hexane, benzene, toluene, ethyl acetate, methanol, ethyl alcohol, tetrahydrofuran or dioxane etc.；Suitable alkali is selected from hydrogen-oxygen
Change sodium, potassium hydroxide, sodium carbonate, potassium carbonate or sodium bicarbonate etc..
Diethyl malonate is dissolved in suitable solvent, adds alkaloids, start stirring, temperature is -10 DEG C and arrives
It is reacted 0.5-48 hours between boiling point, adds intermediate III, continue to stir, temperature is -10 DEG C to reacting 0.5- between boiling point
48 hours, intermediate compound IV is made.Suitable solvent such as chloroform, dichloromethane, carbon tetrachloride, n-hexane, benzene, toluene, acetic acid
Ethyl ester, tetrahydrofuran, N,N-dimethylformamide or dioxane etc.；Alkaloids for example sodium methoxide, sodium ethoxide, potassium tert-butoxide,
Sodium hydroxide, 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 hours between boiling point, is made
Intermediate V.
Compound V is dissolved in suitable solvent, and alkali is added, acyl chlorides (R is slowly added dropwise under stirring3=CH3, it is acetyl
Chlorine；R3=CH2CH3, it is propionyl chloride；R3=CH2CH2CH3, it is butyl chloride), temperature is -10 DEG C to reacting 0.5-48 between boiling point
Hour, enol ester intermediate is made.This intermediate is dissolved in the solvent of suitable intermediates, catalyst is added, temperature is -10 DEG C
It is reacted 0.5-48 hours between boiling point, intermediate VI is made.In suitable solvent, such as chloroform, dichloromethane, four chlorinations
Carbon, n-hexane, benzene, toluene, ethyl acetate, tetrahydrofuran or dioxane etc.；Alkali for example triethylamine, sodium hydroxide, potassium hydroxide,
Sodium carbonate, potassium carbonate or sodium bicarbonate etc.；The solvent of suitable intermediates, such as chloroform, dichloromethane, carbon tetrachloride, acetonitrile, just
Hexane, benzene, toluene, ethyl acetate, tetrahydrofuran, N,N-dimethylformamide or dioxane etc.；Catalyst such as 4- diformazans ammonia
Yl pyridines or acetone cyanohydrin etc..
Intermediate VI is dissolved in suitable solvent, (E)-O- (3- chlorallyls) hydroxylamine hydrochloride is added, temperature is -10
It DEG C is reacted 0.5-48 hours between boiling point, object I is made；Suitable solvent such as methanol, ethyl alcohol, acetonitrile, chloroform, dichloro
Methane, carbon tetrachloride, n-hexane, benzene, toluene, ethyl acetate, tetrahydrofuran or dioxane etc..
Table 1：Part the compounds of this invention and physical property as shown in general 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)。
The compound of Formula I of the present invention has activity of weeding, can be used for agriculturally preventing a variety of weeds.With prior art institute
Disclosed compound is compared, 5- of the invention (3,4- di-substituted-phenyl) -1, and hydroresorcinol class compound not only has excellent
Activity of weeding, and to crop safety.
The invention also includes using compound of Formula I as the Herbicidal combinations of active component.Activearm in the Herbicidal combinations
The weight percentage divided is 1-99%.It further include agriculturally acceptable carrier in the Herbicidal combinations.
The Herbicidal combinations of the present invention can be applied in the form of several formulations.Usually the compound of the present invention is dissolved or divided
It dissipates more readily dispersible when being configured to preparation in carrier to be used as herbicide.Such as：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 usually needs
Surfactant appropriate is added.
The present invention also provides the implementation of controlling weeds, this method includes by the weeding of the present invention of herbicidally effective amount
Composition imposes on the place of the weeds or the weed growth or the surface of growth medium.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.It, can removing in the present invention for certain applications
One or more other herbicides are added in careless composition, thus can generate additional advantage and effect.
The compound of the present invention both can be used alone can also be with other known insecticide, fungicide, plant growth
Conditioning agent or fertilizer etc. mix together.
It should be appreciated that in scope defined by the claims of the present invention, various transformation and change can be carried out.
Specific implementation mode
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.
Synthesize example
The synthesis of embodiment 1, compound 2：
(1) synthesis of intermediate 4- (3,4- Dimethoxyphenyls)-3- butene-2 -one
Veratraldehyde (15.50 grams, 93 mMs) is added into the reaction bulb of 1L, adds acetone 150
5% 75 milliliters of sodium hydrate aqueous solution is added dropwise under ice bath, is added dropwise, keeps room temperature, continues to stir for milliliter and 300 milliliters of water
It mixes 8 hours, TLC detections, the reaction was complete for raw material.Add methylene chloride extraction (150 milliliters × 3), dichloromethane layer washing (250 millis
Rise × 3), saturated common salt washes (250 milliliters), dry, and solvent evaporated obtains 15.27 grams of yellow fluid.
(2) synthesis of intermediate 5- (3,4- Dimethoxyphenyls) -3- hydroxyl -2- cyclohexene -1- ketone
Sodium ethoxide (9.00 grams, 132 mMs) and 50 milliliters of ethyl alcohol is added into 250 milliliters of reaction bulbs, adds the third two
Diethyl phthalate (17.76 grams, 111 mMs), hot add-back stream 1 hour.Reaction solution is cooled to 40 DEG C, be added 50 milliliters of ethyl alcohol and
4- (3,4- Dimethoxyphenyl) -3- butene-2s -one (15.27 grams, 74 mMs), is heated to 60 DEG C, insulation reaction 2 hours.
Gradually there is the solid insoluble in ethyl alcohol to be precipitated in reaction process.After reaction, decompression steams ethyl alcohol, obtains brown fluid.
80 milliliters of sodium hydrate aqueous solution for adding 7% into reaction bulb, after being heated to reflux 6 hours, is down to room temperature, uses acetic acid
Ethyl ester washs (30 milliliters × 2), and it is spare to separate water layer.Water layer enriching hydrochloric acid (30.65 grams, 294 mMs), is heated to flowing back,
Gradually there is solid precipitation in clear solution, after stirring 6 hours, the reaction was complete for raw material.Filtering, it is dry, obtain yellow solid product
8.65 gram.
(3) synthesis of intermediate 5- (3,4- Dimethoxyphenyls) -2- propionos -3- hydroxyl -2- cyclohexene -1- ketone
5- (3,4- Dimethoxyphenyls) -3- hydroxyl -2- cyclohexene -1- ketone (1.15 is added into 100 milliliters of reaction bulbs
Gram, 4.43 mMs) and 40 milliliters of dichloromethane, after adding triethylamine (0.50 gram, 4.94 mMs), solid is gradually molten
It solves, propionyl chloride (0.44 gram, 4.76 mMs) is added dropwise under ice bath, after room temperature continues stirring 2 hours, contact plate, the reaction was complete for raw material.
Extraction, organic phase respectively with dilute 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, decompression steam solvent, obtain yellow fluid.
Obtained yellow fluid is dissolved in 20 milliliters of toluene, be added 4-dimethylaminopyridine (0.25 gram, 2.046 mmoles
You), return stirring reacts 2 hours.TLC shows that the reaction was complete.50 milliliters of water and 50 milliliters of dichloromethanes are added in evaporated under reduced pressure toluene
Alkane, is added 2 milliliters of concentrated hydrochloric acids, and oscillation discards water layer.Organic layer water (40 milliliters) is washed, and (40 milliliters) washings of saturated salt solution are done
It is 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
5- (3,4- Dimethoxyphenyls) -2- propiono -3- hydroxyl -2- cyclohexene-is added into 100 milliliters of reaction bulbs
1- ketone (0.62 gram, 2.037 mMs) and (E)-O- (3- chlorallyls) hydroxylamine hydrochloride (0.30 gram, 2.083 mMs), then
20 milliliters of ethyl alcohol are added, triethylamine (0.25 gram, 2.471 mMs) is finally slowly added dropwise, is stirred to react at 25 DEG C, after 8 hours
Contact plate, the reaction was complete.Decompression steams ethyl alcohol, and silica gel mixed sample crosses column, pillar layer separation (petroleum ether：Ethyl acetate=10:1) it, obtains
0.71 gram of faint yellow solid product, purity 90%.
The synthesis of embodiment 2, compound 3：
(1) synthesis of intermediate 5- (3,4- Dimethoxyphenyls) -2- bytyries -3- hydroxyl -2- cyclohexene -1- ketone
5- (3,4- Dimethoxyphenyls) -3- hydroxyl -2- cyclohexene -1- ketone (1.00 is added into 100 milliliters of reaction bulbs
Gram, 4.03 mMs) and 40 milliliters of dichloromethane, after adding triethylamine (0.45 gram, 4.44 mMs), solid is gradually molten
It solves, butyl chloride (0.43 gram, 4.04 mMs) is added dropwise under ice bath, after room temperature continues stirring 2 hours, contact plate, the reaction was complete for raw material.
Extraction, organic phase respectively with dilute hydrochloric acid, dilute sodium hydroxide aqueous solution and washing, depressurize and steam solvent, obtain yellow by organic layer drying
Fluid.
Obtained yellow fluid is dissolved in 20 milliliters of toluene, be added 4-dimethylaminopyridine (0.25 gram, 2.046 mmoles
You), return stirring reacts 2 hours.TLC shows that the reaction was complete.50 milliliters of water and 50 milliliters of dichloromethanes are added in evaporated under reduced pressure toluene
Alkane, is added 2 milliliters of concentrated hydrochloric acids, and oscillation discards water layer.Organic layer water (40 milliliters) is washed, and (40 milliliters) washings of saturated salt solution are done
It is 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
5- (3,4- Dimethoxyphenyls) -2- bytyry -3- hydroxyl -2- cyclohexene-is added into 100 milliliters of reaction bulbs
1- ketone (0.40 gram, 1.256 mMs) and (E)-O- (3- chlorallyls) hydroxylamine hydrochloride (0.19 gram, 1.319 mMs), then
20 milliliters of ethyl alcohol are added, triethylamine (0.15 gram, 1.482 mMs) is finally slowly added dropwise, is stirred to react at 25 DEG C, after 8 hours
Contact plate, the reaction was complete.Decompression steams ethyl alcohol, and silica gel mixed sample crosses column, pillar layer separation (petroleum ether：Ethyl acetate=10:1) it, obtains
0.29 gram of faint yellow solid product, purity 90%.
Other compounds in table 1 can be made by the method similar with above example.
It is raw to survey example
After active compound acetone solution, stands tap water by 1 ‰ Tween 80 of test requirements document and prepare the to be measured of required concentration
Liquid.Spraying treatment (spraying pressure is carried out with crawler type crops sprayer (Britain Engineer Research Ltd. designs 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 is cultivated after suppression, water drenching in greenhouse according to a conventional method.It waits for that weeds grew to 1.5 leaf phases, chooses and grow uniform examination
Material carries out cauline leaf spraying treatment after seedling, and water treatment is stood as a contrast with 1 ‰ Tween 80.Examination material processing is placed on operation
Hall is placed in greenhouse and manages according to a conventional method after liquid natural air drying, using pouring water from bottom in 48 hours after processing
Method avoids liquid from being washed.Preventive effect of 21 days range estimation investigation test compounds to barnyard grass after processing.
Compound of Formula I has carried out, except the parallel contrast test of barnyard grass 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 refer to DE3329017A1 patents in method into
Row sample preparation.The physical property of KC is shown in Table 3.
Table 3：The physical property of KC：
Security of rice is tested：It is 100cm that quantitative rice paddy seed, which is sowed at sectional area,2Culturing pot in, broadcast rear earthing
1cm is cultivated after suppression, water drenching in greenhouse according to a conventional method.Wait for that rice was grown to 3 leaf phases, choose grow uniform examination material into
Cauline leaf spraying treatment after row seedling stands water treatment as a contrast with 1 ‰ Tween 80.It is placed on dry and ventilated after examination material processing
Place, after liquid natural air drying, is placed in greenhouse and manages according to a conventional method, using the side poured water from bottom in 48 hours after processing
Method avoids liquid from being washed.Range estimation investigation is carried out within 4 weeks after processing, inhibiting rate is various degree of injury compared with the control, 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, after broadcasting
Earthing 1cm is cultivated after suppression, water drenching in greenhouse according to a conventional method.It waits for that wheat was grown to 3 leaf phases, chooses and grow uniform examination
Timber-used crawler type crops sprayer (Britain Engineer Research Ltd. designs production) carries out (spraying of cauline leaf spraying treatment
Pressure 1.95kg/cm2, spouting liquid 50mL/m2, crawler track speeds 30cm/s, nozzle is fan nozzle), examination material processing is placed on operation
Hall is placed in greenhouse and manages according to a conventional method after liquid natural air drying.Routine observation wheat is to test compound after processing
Response situation, carry out within 4 weeks after processing range estimation investigation, inhibiting rate is various degree of injury compared with the control, including kill,
Chlorosis, withered spot, distortion, deformity, growth inhibition or blade calcination etc..
Compound of Formula I is to having high safety after crop seedling, such as compound 2 is in 37.5g a.i./hm2Dosage
Under, the poisoning to rice and wheat is 0.
Claims (4)
1. a kind of 5- (3,4- di-substituted-phenyl) -1, hydroresorcinol class compound, as shown in general formula I：
I
In formula：
R1、R2It is respectively selected from methoxyl group；
R3Selected from ethyl.
2. compound described in claim 1 is used to control the purposes of weeds.
3. a kind of Herbicidal combinations, it is characterised in that containing compound as described in claim 1 and agriculturally acceptable load
Body, the weight percentage of active component is 1-99% in composition.
4. a kind of method of the control weeds of Herbicidal combinations as claimed in claim 3, it is characterised in that：To weeds or weeds
Somatomedin or place on apply weeding effective dose Herbicidal combinations as claimed in claim 3.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510886035.4A CN106831488B (en) | 2015-12-04 | 2015-12-04 | A kind of 5- (3,4- di-substituted-phenyls)-hydroresorcinol class compound and its application |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510886035.4A CN106831488B (en) | 2015-12-04 | 2015-12-04 | A kind of 5- (3,4- di-substituted-phenyls)-hydroresorcinol class compound and its application |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN106831488A CN106831488A (en) | 2017-06-13 |
| CN106831488B true CN106831488B (en) | 2018-09-28 |
Family
ID=59150742
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510886035.4A Active CN106831488B (en) | 2015-12-04 | 2015-12-04 | A kind of 5- (3,4- di-substituted-phenyls)-hydroresorcinol class compound and its application |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106831488B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109485600A (en) * | 2017-09-11 | 2019-03-19 | 山东先达农化股份有限公司 | Compound of fluorine-containing chloropyridine oxime ester structure and its preparation method and application and a kind of herbicide |
| 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 |
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 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN106831488A (en) | 2017-06-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101279951B (en) | 2-pyrimindinyloxy (pyrimindinylthio) benzoxy enoates compound and application thereof | |
| CN104649973B (en) | Pyrazole amide compound and application thereof | |
| CN102015679A (en) | 1-substituted pyridyl-pyrazolyl amide compounds and uses thereof | |
| CN106831488B (en) | A kind of 5- (3,4- di-substituted-phenyls)-hydroresorcinol class compound and its application | |
| CN105801513B (en) | N- with activity of weeding replaces alkyl virtue phenoxy base Propionamides compound and its preparation and application | |
| CN108689921A (en) | It is a kind of virtue phenoxy base Propionamides compound preparation method with application | |
| CN112624989A (en) | Amide compound and application thereof | |
| CN112624973B (en) | Carboxylic acid ester compound and application thereof | |
| CN111303126B (en) | Pyrazole amide compound and application thereof as herbicide | |
| CN112624974B (en) | Cinnamate compound and application thereof | |
| CN106831631B (en) | A kind of 6- chloro benzo dislikes (thiophene) azoles oxygroup phenoxy propionic acid ester type compound and its application | |
| CN109867624B (en) | 3-fluoro-5-chloropyridinyloxy phenoxypropanamide compound and application thereof | |
| CN106831618B (en) | A kind of quaternary ammonium compound and its application | |
| JPS61257974A (en) | Pyrazole derivative, production thereof, and selective herbicide | |
| CN115279738A (en) | Pyrazole carboxylic ester compound and application thereof | |
| CN104649995B (en) | A kind of 6 chloro benzo oxazole epoxide phenoxy propionic acid allyl ester type compound and its application as herbicide | |
| CN109553615A (en) | A kind of pyrimidine salt compounds and application thereof | |
| CN101096338B (en) | Benzoate compounds and uses thereof | |
| CN112939958B (en) | Condensed ring acyl compound and application thereof | |
| CN1927811B (en) | Compound of 4-benzoxybutenolate and application thereof | |
| CN103833743B (en) | Thiazolyl pyrazolyl acrylonitrile compound and application thereof | |
| CN107082768A (en) | A kind of aryloxy acetic acids Aurone compound and the application on agricultural chemicals | |
| CN103833670B (en) | 2-chlorine thiazolyl acrylonitrile compounds and application thereof | |
| CN116217487A (en) | Benzoyl pyrazole compound and application thereof | |
| CN108003142A (en) | A kind of preparation method and application of virtue phenoxy propionyl hydrazine class compound |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |