CN1028314C - Composition for preventing and controlling weeds in corn field - Google Patents
Composition for preventing and controlling weeds in corn field Download PDFInfo
- Publication number
- CN1028314C CN1028314C CN 93101976 CN93101976A CN1028314C CN 1028314 C CN1028314 C CN 1028314C CN 93101976 CN93101976 CN 93101976 CN 93101976 A CN93101976 A CN 93101976A CN 1028314 C CN1028314 C CN 1028314C
- Authority
- CN
- China
- Prior art keywords
- compound
- composition
- formula
- preventing
- corn field
- 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.)
- Expired - Lifetime
Links
- 241000196324 Embryophyta Species 0.000 title claims abstract description 14
- 240000008042 Zea mays Species 0.000 title claims abstract description 13
- 235000002017 Zea mays subsp mays Nutrition 0.000 title claims abstract description 13
- 239000000203 mixture Substances 0.000 title claims abstract description 13
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 title abstract description 12
- 235000005822 corn Nutrition 0.000 title abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- 238000000034 method Methods 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- -1 Pyrimidine compound Chemical class 0.000 claims description 3
- 238000007796 conventional method Methods 0.000 claims description 2
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims 1
- 235000009973 maize Nutrition 0.000 claims 1
- 239000004009 herbicide Substances 0.000 description 12
- 230000002363 herbicidal effect Effects 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000003814 drug Substances 0.000 description 5
- YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 description 5
- 229940100389 Sulfonylurea Drugs 0.000 description 4
- HYJODZUSLXOFNC-UHFFFAOYSA-N [S].[Cl] Chemical compound [S].[Cl] HYJODZUSLXOFNC-UHFFFAOYSA-N 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- RCEAADKTGXTDOA-UHFFFAOYSA-N OS(O)(=O)=O.CCCCCCCCCCCC[Na] Chemical compound OS(O)(=O)=O.CCCCCCCCCCCC[Na] RCEAADKTGXTDOA-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 150000003230 pyrimidines Chemical class 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- 238000004381 surface treatment Methods 0.000 description 2
- 238000001238 wet grinding Methods 0.000 description 2
- 240000002791 Brassica napus Species 0.000 description 1
- 235000011293 Brassica napus Nutrition 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- 244000058871 Echinochloa crus-galli Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 108090000723 Insulin-Like Growth Factor I Proteins 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 241000209510 Liliopsida Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 102000013275 Somatomedins Human genes 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- WLDHEUZGFKACJH-UHFFFAOYSA-K amaranth Chemical compound [Na+].[Na+].[Na+].C12=CC=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(O)=C1N=NC1=CC=C(S([O-])(=O)=O)C2=CC=CC=C12 WLDHEUZGFKACJH-UHFFFAOYSA-K 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 241001233957 eudicotyledons Species 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 231100000225 lethality Toxicity 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000010458 rotten stone Substances 0.000 description 1
- 230000011218 segmentation Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical class O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention provides a composition for preventing and controlling weeds in corn fields, which consists of a compound shown in a formula and a suitable agriculturally acceptable carrier.
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 5.2g25% 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 1.0g2-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 (0x10), 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 15 after straight 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
50Ic
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 chlorine sulphur swells the formula Iization
(title) compound
Agent weighs 2124
(gram/mu)
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 resistance, so be weed killer 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 (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 | Composition for preventing and controlling weeds in corn field |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 93101976 CN1028314C (en) | 1993-02-27 | 1993-02-27 | Composition for preventing and controlling weeds in corn field |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1080116A CN1080116A (en) | 1994-01-05 |
| CN1028314C true 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 | Composition for preventing and controlling weeds in corn field |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1028314C (en) |
Families Citing this family (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 |
| 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 |
| CA2834965C (en) | 2011-05-04 | 2019-08-20 | 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 |
| ES2687545T5 (en) | 2012-12-13 | 2022-08-31 | Bayer Cropscience Ag | Use of ALS-inhibiting herbicides to control unwanted vegetation in Beta vulgaris plants tolerant to ALS-inhibiting herbicides |
| CN112661704B (en) * | 2020-12-22 | 2023-09-05 | 南开大学 | Monosulfuron derivative, preparation method thereof, herbicide and weeding method |
-
1993
- 1993-02-27 CN CN 93101976 patent/CN1028314C/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CN1080116A (en) | 1994-01-05 |
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Expiration termination date: 20130227 Granted publication date: 19950503 |