CN1080116A - Control of maize field weed composition - Google Patents
Control of maize field weed composition Download PDFInfo
- Publication number
- CN1080116A CN1080116A CN 93101976 CN93101976A CN1080116A CN 1080116 A CN1080116 A CN 1080116A CN 93101976 CN93101976 CN 93101976 CN 93101976 A CN93101976 A CN 93101976A CN 1080116 A CN1080116 A CN 1080116A
- Authority
- CN
- China
- Prior art keywords
- compound
- formula
- composition
- control
- field weed
- 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.)
- Granted
Links
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention provides a kind of control of maize field weed composition, it is made up of acceptable carrier on formula (I) compound and the suitable agricultural.
Description
The present invention relates to crops weeds in field composition, be specially adapted to corn field.
Up to now, contain the existing a lot of reports of Herbicidal combinations of sulfonylureas pyrimidines, as US-4,191,533 disclose following formula: compound
As weed killer herbicide.
US-4,501,607 disclose compound
As herbicides compounds effectively, or the like.
In being disclosed as these sulfonylureas pyrimidines, most to the general injury effect of plant, promptly it is not only to the undesirable plant sensitivity, and also harmful equally to some crops.So to some concrete single crop, weed killer herbicide is not desirable selection like this.As to corn, up to the present, also be not particularly suitable for its fine herbicide.
The present invention just is being based on this and is conceiving and finish, and the inventor finds following formula (I) sulfonylureas pyrimidine compound through a large amount of research
Be the good weed killer herbicide of corn field, it not only has inhibitory action to many weeds, and harmless to corn, and through the greenhouse soil processes and displays, it also has good resistance to soybean.
Given this, one of purpose of the present invention provides Herbicidal combinations good between a kind of corn field.
In above-mentioned Herbicidal combinations, formula (I) compound that contains effective dose is an active ingredient, also has agricultural to go up acceptable carrier.Effective dose described here, the amount of using always with this area professional is as the criterion, it contains 0.1-99%(weight in composition usually), be preferably 0.5-50%(weight).
Acceptable carrier on the agricultural, the professional is normally used for this area, and solid or the liquid-carrier harmless to crop, specifically for example: talcum powder, clay, kaolin, algae tripoli, lignin, sodium lignin sulfonate, lauryl sodium sulfate, water, hydro carbons, ethers, ketone, arene, amide-type and surfactant, emulsifier or the like.
Another object of the present invention provides the preparation method of the present composition, it comprises, formula (I) compound and the above-mentioned carrier of effective dose are formed so that method conventional in the agriculture preparation is all mixed, these methods are as pulverizing, stir or the like, formulation can be commonly used in the agriculture preparation, but as wet-milling, missible oil and pulvis etc.
The present invention also provides the application of the present composition, it comprises an amount of present composition is imposed on crop (corn) Tanaka that will cut weeds with conventional method, these methods comprise soil, seed and active component leaf surface treatment etc., the common 0.5-4g active component of amount described here/mu is preferably 1-2g/ mu.
Formula (I) compound is not specifically addressed in disclosed document, and it is with formula (II) compound
With formula
The pyrimidine compound of (III) reacts in The suitable solvent and under the suitable temperature and gets.
The synthetic method of the sulfonylisocyanates of formula (II) compound is referring to US-3, and 169,719 etc.
By the following examples the present invention is specified, but for illustrative purposes only rather than the restriction the present invention.
Embodiment 1: the preparation of formula (I) compound:
In the reaction bulb of 100ml, add 20.3g concentrated hydrochloric acid and 10ml water, slowly add 6.9g(0.05mol) ortho-nitraniline, be cooled to below 5 ℃, add 3.5g(0.051mol) aqueous solution of natrium nitrosum, this reaction mixture adding is contained 67ml glacial acetic acid, 3.2g(0.05mol) SO
2And in the reaction bulb of catalytic amount CuCl, stir after 1 hour, in reactant liquor impouring 100ml frozen water, use extracted by ether, slough ether in the ether layer and can get slightly ortho-nitrophenyl sulfonic acid chloride 8.2g.
The crude product and the 10ml ether of above-mentioned gained are added in the 100ml reaction bulb, and the ammoniacal liquor in adding 5.2g5% below 5 ℃ stops reaction after 0.5 hour, leach solid, the dry ortho-nitrophenyl sulfonamide 6.2g that gets, and total recovery is 62%, mp.196.5-198.5 ℃.
In the 100ml reaction bulb, add 3.0g(0.015mol) the ortho-nitrophenyl sulfonamide, 30ml toluene and a small amount of triethylamine, 6.7g(0.053mol) oxalyl chloride is kept reaction 6 hours between 50-90 ℃.Cooling is filtered, and sloughs solvent, residue is added contain in the reaction bulb of 1.0g 2-amino-4-methylpyrimidine and 20ml acetonitrile, filters after 1.5 hours, and the gained solid is purified, promptly gets product 2.6g, yield 51%, mp.191.0-191.5 ℃.
Embodiment 2
The preparation of dust agent
10 parts of compounds of the present invention and 90 parts of talcum powder are mixed in mechanical crushing mixture machine, grind, until obtaining required particle diameter form of free flowing powders.
Embodiment 3
The preparation of wettable powder
With 25 parts of The compounds of this invention and 25 parts of artificial fine particles of silica, the kaolin of 2 parts of lauryl sodium sulfate, 3 parts of sodium lignin sulfonates, 45 parts of segmentations is ground and mixed together, but until obtaining the wet-milling that average grain diameter is about 50 microns.
Embodiment 4:
The preparation of missible oil
10mg formula (I) compound is added the 0.3ml dimethyl formamide, and 1 emulsifier (O π 10), add water to 100ml again and stir, obtain emulsifiable concentrate.
The biologicall test test:
Ic
50Measure:
3 milliliters of medicament to be measured and 25 rape seeds that are dissolved in the innoxious solvent are put into the culture dish that is lined with 6 centimetres of 2 filter paper diameters, and medicament to be measured will have 4 to 5 concentration at least, and each concentration repeats 2 times, establish the clear water contrast.All culture dishes are placed in 28 ℃ of constant temperature darkrooms, after 45 hours, measure rape epicotyl length.Between weed killer herbicide concentration and the growth inhibition degree linear relation is arranged, the susceptibility of sulfonylurea is low to moderate 0.0003ppm.Compare with blank, calculate and suppress percentage.Ask Ic with method of least squares
50
The potted plant evaluation of pesticide effectiveness:
With several responsive single, double cotyledon weeds and crop seed kind in somatomedin, through the identical time, when monocotyledon tool two leaves wholeheartedly, dicotyledon 3 to 4 leaves are when (comprising cotyledon), after other uses the same method and repeats plantation, do cauline leaf and soil treatment with the medicament to be measured that is dissolved in the innoxious solvent, handle after 15 to 21 days, divide the overground part fresh weight of another name plant, handle the blank ratio with clear water, calculate it and suppress percentage, kill careless power and to crop safety in order to evaluation.
Bioassay results
Ic
50
Ic
50γ
Chlorine sulphur grand 7.87 * 10
-7M 0.95
Formula I compound 4.13 * 10
-7M 0.96
Greenhouse pot culture drug effect (soil treatment)
Medicament (title) chlorine sulphur swells formula I compound
Heavy (gram/mu) 2124 of agent
Wheat T T T T
Oat T T T T
Jowar S S-1 S-1 S
Corn S T T T
Barnyard grass grass S-1 S-1 S-1 S-1
Soybean S-1 T T T
Rape S S S S
Clover T-1 T-1 T-1 S-1
Flax T T-1 T-1 T-1
Three-coloured amaranth S S S S
* T is anti-among the resistance T-1
S is quick among the responsive S-1.
Leaf surface treatment:
The drug dose corn
(gram/mu)
Chlorine sulphur swells 2 S
Formula (I) compound 1 T
2 T
4 T-1
From above-mentioned result of the test as can be known, Herbicidal combinations of the present invention is compared with chlorine sulphur is grand, noxious plant is had same lethality, but corn is shown good antibiosis, so be herbicide between a kind of good corn field.
Claims (4)
1, a kind of composition of control of maize field weed is characterized in that wherein containing following formula formula (I) compound of effective dose
And agricultural goes up acceptable carrier
2, preparation claim 1 method for compositions is characterized in that formula (I) compound and the agriculture acceptable carrier of going up of effective dose are mixed with conventional method
3,, it is characterized in that formula (I) compound wherein is with following formula: compound according to the method for claim 2
Pyrimidine compound with following formula
The reaction and get
4, the application of claim 1 composition is characterized in that composition with an amount of claim 1 imposes on and desires the place of cutting weeds.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 93101976 CN1028314C (en) | 1993-02-27 | 1993-02-27 | Composite for preventing and killing weeds in the corn field |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 93101976 CN1028314C (en) | 1993-02-27 | 1993-02-27 | Composite for preventing and killing weeds in the corn field |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1080116A true CN1080116A (en) | 1994-01-05 |
| CN1028314C CN1028314C (en) | 1995-05-03 |
Family
ID=4983888
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 93101976 Expired - Lifetime CN1028314C (en) | 1993-02-27 | 1993-02-27 | Composite for preventing and killing weeds in the corn field |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1028314C (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1038679C (en) * | 1994-12-07 | 1998-06-10 | 南开大学 | Sulfonylurea compound herbicide |
| CN1063611C (en) * | 1996-07-01 | 2001-03-28 | 南开大学 | Compound herbicide preparation |
| EP2052606A1 (en) | 2007-10-24 | 2009-04-29 | Bayer CropScience AG | Herbicide combination |
| DE102008037620A1 (en) | 2008-08-14 | 2010-02-18 | Bayer Crop Science Ag | Herbicide combination with dimethoxytriazinyl-substituted difluoromethanesulfonylanilides |
| WO2012049266A1 (en) | 2010-10-15 | 2012-04-19 | Bayer Cropscience Ag | Use of als inhibitor herbicides for control of unwanted vegetation in als inhibitor herbicide tolerant beta vulgaris plants |
| WO2012150333A1 (en) | 2011-05-04 | 2012-11-08 | Bayer Intellectual Property Gmbh | Use of als inhibitor herbicides for control of unwanted vegetation in als inhibitor herbicide tolerant brassica, such as b. napus, plants |
| WO2014090760A1 (en) | 2012-12-13 | 2014-06-19 | Bayer Cropscience Ag | Use of als inhibitor herbicides for control of unwanted vegetation in als inhibitor herbicide tolerant beta vulgaris plants |
| CN112661704A (en) * | 2020-12-22 | 2021-04-16 | 南开大学 | Monosulfuron-methyl derivative, preparation method thereof, herbicide and weeding method |
-
1993
- 1993-02-27 CN CN 93101976 patent/CN1028314C/en not_active Expired - Lifetime
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1038679C (en) * | 1994-12-07 | 1998-06-10 | 南开大学 | Sulfonylurea compound herbicide |
| CN1063611C (en) * | 1996-07-01 | 2001-03-28 | 南开大学 | Compound herbicide preparation |
| EP2052606A1 (en) | 2007-10-24 | 2009-04-29 | Bayer CropScience AG | Herbicide combination |
| DE102008037620A1 (en) | 2008-08-14 | 2010-02-18 | Bayer Crop Science Ag | Herbicide combination with dimethoxytriazinyl-substituted difluoromethanesulfonylanilides |
| US10544426B2 (en) | 2010-10-15 | 2020-01-28 | Bayer Intellectual Property Gmbh | Methods of using ALS inhibitor herbicides for control of unwanted vegetation in ALS inhibitor herbicide tolerant beta vulgaris plants |
| EP3284346A1 (en) | 2010-10-15 | 2018-02-21 | Bayer Intellectual Property GmbH | Use of als inhibitor herbicides for control of unwanted vegetation in als inhibitor herbicide tolerant beta vulgaris plants |
| WO2012049266A1 (en) | 2010-10-15 | 2012-04-19 | Bayer Cropscience Ag | Use of als inhibitor herbicides for control of unwanted vegetation in als inhibitor herbicide tolerant beta vulgaris plants |
| US11371057B2 (en) | 2010-10-15 | 2022-06-28 | Bayer Intellectual Property Gmbh | Methods of using ALS inhibitor herbicides for control of unwanted vegetation in ALS inhibitor herbicide tolerant beta vulgaris plants |
| WO2012150333A1 (en) | 2011-05-04 | 2012-11-08 | Bayer Intellectual Property Gmbh | Use of als inhibitor herbicides for control of unwanted vegetation in als inhibitor herbicide tolerant brassica, such as b. napus, plants |
| US9370183B2 (en) | 2011-05-04 | 2016-06-21 | Bayer Intellectual Property Gmbh | Use of ALS inhibitor herbicides for control of unwanted vegetation in ALS inhibitor herbicide tolerant Brassica, such as B. napus, plants |
| WO2014090760A1 (en) | 2012-12-13 | 2014-06-19 | Bayer Cropscience Ag | Use of als inhibitor herbicides for control of unwanted vegetation in als inhibitor herbicide tolerant beta vulgaris plants |
| CN112661704A (en) * | 2020-12-22 | 2021-04-16 | 南开大学 | Monosulfuron-methyl derivative, preparation method thereof, herbicide and weeding method |
| CN112661704B (en) * | 2020-12-22 | 2023-09-05 | 南开大学 | Monosulfuron derivative, preparation method thereof, herbicide and weeding method |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1028314C (en) | 1995-05-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN1033452C (en) | 1-{[O-(cyclopropylcarbonyl) phenyl] sulfamoyl}-3-(4,6 dimethoxy-2-pyrimidinyl) urea and method for preparation thereof | |
| CN1327729A (en) | Metolachlor synergism herbiciding composition | |
| CN1820599A (en) | Synergistic herbicidal compositions comprising mesotrione | |
| CN1222828A (en) | Herbicidal mixtures | |
| EP0230209A2 (en) | Microbicides | |
| CN1190651A (en) | 2-alkoxyphenoxy sulfuric urea with heterocyclic ring and application used as weedicide and plant growth regulator | |
| CN1968604A (en) | Herbicidal composition | |
| CN1028314C (en) | Composite for preventing and killing weeds in the corn field | |
| CN1052852C (en) | Herbicidal composition contg. prpisochlor | |
| PL155723B1 (en) | Pesticide in particular against insects, nematodes and mites | |
| CN85101424A (en) | The preparation method of imidazolone and the application aspect plant protection thereof | |
| CN1016575B (en) | Synergistic herbicide combinations and method of preparation | |
| SU1556539A3 (en) | Method of producing substituted 2-phenyliminoxazolidinons | |
| CN1044959C (en) | Herbicidal method in rice | |
| CN87100276A (en) | 1, the preparation method of 2-double-basis substituted piperidine and in application in plant protection | |
| CN1781375A (en) | Bicao mixture | |
| CN1050537A (en) | Sulphonamide analog derivative with herbicide effect | |
| JPH1059808A (en) | Herbicidal composition containing pyroglutamic acid or its salt | |
| CN111988996B (en) | Improving yield of nut bearing plants | |
| JPH029804A (en) | Herbicidal composition | |
| CN1165231C (en) | Herbicidal composition | |
| CN1060760A (en) | Synergistic herbicidal agents | |
| JPS621921B2 (en) | ||
| CN1088554C (en) | Propisochlor containing herbicide composition | |
| JP2000053509A (en) | Herbicide composition |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C06 | Publication | ||
| PB01 | Publication | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C17 | Cessation of patent right | ||
| CX01 | Expiry of patent term |
Expiration termination date: 20130227 Granted publication date: 19950503 |