AU672121B2 - Stable herbicidal combination compositions - Google Patents
Stable herbicidal combination compositions Download PDFInfo
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- AU672121B2 AU672121B2 AU70282/94A AU7028294A AU672121B2 AU 672121 B2 AU672121 B2 AU 672121B2 AU 70282/94 A AU70282/94 A AU 70282/94A AU 7028294 A AU7028294 A AU 7028294A AU 672121 B2 AU672121 B2 AU 672121B2
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- AU
- Australia
- Prior art keywords
- composition according
- herbicide
- white carbon
- melting
- sulfamoyl
- Prior art date
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Classifications
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
-
- 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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
- A01N33/18—Nitro compounds
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- 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
- A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
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- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (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)
Description
UO 00 1 STABLE HERBICIDAL COMBINATION COMPOSITIONS BACKGROUND OF THE INVENTION In order to control a wide variety of troublesome broadleaf and grass weed species in the presence of cereal crops, especially in rice culture/ (upland and paddy), a combination application of one or more herbicides is generally required. The compound, 1- {[o-(cyclopropyicarbonyl)phenyl]sulfamoyl}-3-(4,6dimethoxy-2-pyrimidinyl)urea is a crop-selective herbicide which is highly effective in controlling broadleaf weeds and sedges and is described in U.S. 5,009,699. In present 1 day agronomic practice a number of effective grass herbicides are available which are selective in cereal crops such as dinitroaniline herbicides, thiocarbamate .sa' herbicides and chloroacetamide herbicides. However, many of these herbicides are liquids or low-melting solids and when one or more are used in combination with the abovesaid sulfamoyl urea to achieve broad spectrum weed control in the presence of cereal crops, the sulfamoyl urea compound may become unstable with the passage of time and lose its efficacious properties.
It is, therefore, an object of this invention to provide a stable combination herbicide composition for the control of noxious grass and broadleaf plant species and sedges which plague cereal crops, especially upland rice crops and paddy rice fields.
SUMMARY OF THE INVENTION This invention relates to a stable herbicidal composition which comprises l-{[o-cyclopropylcarbonyl)phenyl]sulfamoyl}-3-(4,6-dimethoxy-2-pyrimidinyl)urea in combination with one or more low-melting or liquid herbicides and alkaline white carbon. Advantageously, the herbicidal combination composition of the invention may be used to provide excellent control of a broad spectrum of grass and broadleaf weeds and sedge in the presence of growing, seeded or transplanted cereal crop plants, even after prolonged storage.
DESCRIPTION OF THE INVENTION Cereal grains such as rice, wheat, barley, oats and rye are considered to be among the most important food c:-ops. For example, rice is the major dietary component for greater than one-third of the world's population.
Grain production, to be efficient, often requires the use of two or more herbicides in a combination application to control the full spectrum of noxious plant species, for example, those which plague rice paddy fields and upland rice crops.
S, .The compound 1- [o-(cyclopropylcarbonyl)- S phenyl]sulfamoyl}-3-(4,6-dimethoxy-2-pyrimidinyl)urea, hereinafter referred to as the sulfamoyl urea compound, is a potent crop-selective herbicide which may be used in very low quantities and is especially effective for the control of sedges and broadleaf weed species in the presence of cereal crops such as barley, wheat, oats, and rye, as well as rice. This sulfamoyl urea compound is described in U.S.
5,009,699. Readily available, low-melting or liquid, herbicidal agents which are chiefly used for weed control in cereal crop production and are especially effective for control of annual grass weeds are: dinitroaniline herbicides such as pendimethalin, trifluralin and the like; thiocarbamate herbicides such as esprocarb, thiobencarb, molinate and the like and chloroacetamide herbicides such as butachlor, pretilachlor, metolachlor, alachlor and the like.
A combination of the sulfamoyl urea compound with one or more of the low-melting or liquid herbicides would offer an efficient and effective means of controlling a broad spectrum of grass and broadleaf weeds and sedges in cereal crop production. However, the sulfamoyl urea compound demonstrates unstable properties in the presence of certain low-melting or liquid herbicides and thereby loses efficacy and greatly reduces the potential control of broadleaf weeds and sedges. By low-melting herbicides, it is meant an herbicidal compound with a melting point of or less.
Surprisingly, it has been found that an herbicidal combination composition comprising the sulfamoyl urea compound in combination with one or more low-melting or liquid herbicides in the presence of alkaline white carbon demonstrates excellent stability, effective broad spectrum weed control and desirable physical properties even after stanei'ng for long periods of time. Alkaline white carbon designates silicon dioxide (SiO 2 sorbtive carriers with a pH of about 9-12, preferably about 10-11.
Among the alkaline white carbon products suitable for use in the composition of the invention are Carplex #100 or Carplex #1120 (manufactured by Sbionogi Pharmaceutical Toksil AL-1 (manufactured by Tokuyama Soda Co.), Nipsil NA (manufactured by Nippon Silica Kogyo Co.) and the like, preferably Carplex #100 or Carplex #1120.
The Carplex white carbons comprise amorphous *2'h hydrous silicon dioxide synthesized by the wet process and are generally known as a type of precipitated silica. The Carplex white carbons are formed by agglomerate structuring from globular basic particles of about 20 to 30 mA.
Further description of the characteristics and properties of the Carplex white carbon including Carplex #100 and S Carplex #1120, is available from the trade brochure entitled "CARPLEX® SHIONOGI, Amorphous hydrous silicon dioxide (Si0 2 .n H20)" by Shionogi Co., Ltd., Japan, which is incorporated herein by reference.
In one embodiment of the invention, the stable herbicidal combination composition may contain about 0.05 25.0% by weight of the sulfamoyl urea compound, preferably about 0.05 about 1 65% by weight of a low-melting or liquid herbicide and about 2 30% by weight of alkaline white carbon.
In actual practice, the composition of the invention may be formulated in any of the conventional dry forms such as dusts, dust concentrates, wettable powders, fine granulars, granulars, water dispersable granulars and the like utilizing agronomically acceptable adjuvants including carriers, surfactants, binders and the like.
Among the carriers suitable for use in these formulations are clay, talc, diatomaceous earth, bentonite, calcium carbonate, and the like. Conventional surfactants which may be used in the above formulations are non-ionic surfactants such as polyoxyethylene alkylaryl other, polyoxyethylene styrylphenyl ether, polyoxyethylene sorbitan fatty acid ester and the like, and ionic surfactants such as alkylsulfate, alkylarylsulfonate, alkylsulfate ester, ligninsulfonate, alkylnapthalene sulfonate formalin condensate, sulfate of polyoxyethylene alkylaryl ether, alkylamine salt, dialkylsulfosuccinate, polycarbonate and the like. Binders such as carboxymethylcellulose may be used to improve the hardness of granule formulations.
For a more clear understanding of the invention, specific examples thereof are set forth below. These examples are merely illustrative and are not to be understood as limiting the scope and underlying principles o.
of the invention in any way.
o tea a I EXAMPLE 1 Preparation Of Granular Combination Compositions With 1- {[o-(cyclopropylcarbonvl)-phenyllsulfamoyl}-3-(4,6dimethoxy-2-pyrimidinyl)urea And A Liquid Herbicide.
The liquid herbicide used in this example is esprocarb, a thiocarbamate herbicide.
The title sulfamoyl urea compound is pulverized and blended with either white carbon or alkaline white carbon. This blend is then mixed with clay or talc or CaCO 3 bentonite and surfactants. The resultant mixture is blended, kneaded with water and extruded through a 0.7-15 S' mm mesh screen. The resultant granules are dried, cut and sprayed with the liquid herbicide (esprocarb).
Using the above procedure, the following granular compositions are obtained and shown in Table I.
e t
MEMONOMMEM
6 TABLE I wt/wt t
INGREDIENT
Sulfamoyl urea (91.9!k pure) Esprocarb (94.3-0 pure) White Carbon' (ph 5.5-6.3) White Carbon' (ph 7-0-8.0) Alkaline White Carbon: 3 (pH 10.1-10.6) Clay CaCO 3 Talc Bentonite Na Polycarbonate' Dialkyl sulfosuccinate' Styrenated phenol sulfate/ alkylbenzene sulfonate' Epoxylated soybean oil' Carbox-ymethylcellulose Na 8 1) Carplex #80 (Shionogi Pharmaceutical Co-) 2) Carplex #67 (Shionogi Pharmaceutical Co.)
A
0.67 22 .94 15.0
B
0. G7 22.94 1.03
C
0.67 22 .94 1.03 17.5 28.93 18.86 18.8G
D
0 .67 22 .94 0 .83 17.5 20 .06 30.00 3.00 3.00
E
0.6G7 22 .94 17.5
F
0.67 22 .94 17.5 22.89 30.00 3 .00 3.00 25.00 3 .00 3.00 2 .00 30.00 3.00 3.00 2.00 1.00 30.00 3 .00 3.00 2.00 1.00 26.09 30.0 0.8 2.00 Ltd.) 5) Neocol YSK (Dai-ichi Kogyo 6) New Kalgen TG-74 (Takernoto Seiyako Co.
Oil Fat Ltd.) 3) Carplex #100 (Shionogi Pharmaceutical Co.) 7) New Kalgen 800 (Takemoto Oil Fat Co., Ltd.)' 4) Shallol AN103P (Dai-ichi Kogyo Seiyaku Co-,Ltd.) 8) Cellogen 7A CDai-ichi Kogyo Seiyako Co., Ltd.) EXAMPLE 2 Comparative Stability Evaluation of Compositions Contan.Ainq (cyclopropylcarbonyl) -phenyll sulfamovl}-3- 6-.
dimethoxv-2-pyrimidinvl)urea And A Liaruid Hexbicide.
Test compositions prepared in Examnple 1 are placed in a screw-capped glass sample bottle and stored in a constant temperature oven set at 40 0 C. The samples are analyzed for active ingredient content after 0, 1, 2 and 3 month periods. Analyses are perforr.ed by reverse phase high speed liquid chromatography.
The percent recovery of the sulfamoyl urea compound is calculated using the equation shown below.
%Recovery =Storage guantity x 100 The results are shown in Table II.
TABLE 11 Evaluation Of The Stability Of The Sulfamoyl Urea In A Combination Composition Herbicide And Alkaline White Carbon With A Liquid Storage at 40 0
C
Test Samole White Carbon Initial Ouantity 1 2 month Quantity 1 2 month Recovery~ 3 month Quantity' 3 month Recovery Carplex Carplex Carplex Carplex Carplex Carp lex #80 #67 #100 #100 #100 #100 5.5-6.3 7.0-8.0 10.1-10.6 10. 1-10. 6 10.1-10.6 10. 1-10 .6 0.58 0 .59 0.53 0.58 0.58 0.63 0.28 0.49 0.55 0.64 0.55 0.54 48.3 83 .0 100 100 94 .8 85 .7 0.16G 0.29 0.33 0.52 0.43 0.53 32.8 49.2 62.3 89. 7 74.1 84. 1 'Sulfamoyl urea. compound-
II
9 EXAMPLE 3 Preparation of Granular Combination Compositions Containing 1-{[o-(cyclopropylcarbonyl)-phenyl]sulfamoyl}-3-(4,6dimethoxy-2-pyrimidinvl)urea And A Low-melting Herbicide The low-melting herbicide used in this example is pendimethalin, a dinitroaniline herbicide.
The sulfamoyl urea compound is mixed with a portion of the alkaline white carbon. Pendimethalin is melted using a water bath and blended with the remaining alkaline white carbon. The two mixtures are blended together and the remaining ingredients are added. The resultant mixture is blended, kneaded with water and extruded through an 0.7-15 mm mesh screen. The resultant granules are dried and cut.
Using the above procedure, the compositions shown 0 on Table III are prepared.
Table III Wt/Wt INGREDIENTS A B Sulfamoyl urea (91.9% pure) 0.67 0.67 Pendimethalin (91.8% pure) 5.76 5.76 S Alkaline White Carbon 1 5.98 5.98 (pH 10.1-10.6) Clay 41.59 Talc 41.59 Bentonite Na 40.0 40.0 Polycarbonate type anionics 2 3.0 Dialkylsulfosuccinate 3 3.0 1) Carplex #100 (Shionogi Pharmaceutical Co.) 2) Shallol AN103P (Dai-ichi Kogyo Seiyaku Co., Ltu.) 3) Neocol YSK (Dai-ichi Kogyo Seiyaku Co., Ltd.) r I= I EXAMPLE 4 Stability Evaluation Of Compositions Containing (cyclopropylcarbonyl)-phenyl]sulfamoyl}-3-(4,6-dimethoxy-2pyrimidinyl)urea And A Low-Melting Herbicide Test compositions prepared in Example 3 are placed in a screw-capped glass sample bottle and stored in a constant temperature oven set at 40 0 C. The samples are analyzed for active ingredient content after 0, 1, 2 and 3 month periods. Analyses are performed by reverse phase high speed liquid chromatography. The percent recovery of the sulfamoyl urea compound is calculated as described in Example 2. The data are shown below in Table IV.
o
S
a S 0 S C* TAB3LE IV Evaluation Of The Stability Of The Sulfamoyl Urea In A Combination Composition With A Low-melting Herbicide And Alkaline White Carbon Test Sarnole III A White Carbon Carplex #100 PHi 10.1-10.6 Initial Ouant i t 0.41S Storage at 40 0
C
2 month 2 month 3 month Ouantity %0 Recovery Quantity 0.435 100 0.443 3 month %Recovery 100 III B Carplex #100 10.1-10.6 0420429860342. 0.428 0.422 98-6 0.394 92.0 12 EXAMPLE V Preparation Of Granular Combination.Compositions With 1- (cyclopropylcarbonyl) -phenvllIsulfarno 11-3- (4,6dimethoZxy-2-pvnimidinyl)urea And A ILow-Meltingf-Solid Or A Liq'uid Herbicide Using the procedures described in Examples I and III, the following low-melting or liquid herbicides may be used in combination with the title sulfawoyl urea to prepare a stable herbicidal composition.
*9 H-erbide Trifluralin Thiolrencarb Molinate B' atachlor Pretilachlor Alachior Metolachlor mp ('C 48 .5 -49' 3 liquid liquid liquid 39.5 *-41.5* liquid
S.
S
*S4SSS
Claims (12)
1. A stable herbicidal composition which 'is characterized by a sulfamoyl urea compound, (cyclopropylcarbonyl)phenyl]sulfamoyl}-3-(4,6-dimethoxy-2- pyrimidinyl)urea, one or more low-melting or liquid herbicides and alkaline white carbon.
2. The composition according to claim 1 wherein the low-melting or liquid herbicide is selected from the group consisting of a dinitroaniline herbicide, a thiocarbamate herbicide and a chloroacetamide herbicide and the alkaline white carbon has a pH of about 10-11.
3. The composition according to claim 1 which is characterized by on a weight basis about 0.05-25.0% of the eo-m sulfamoyl urea compound, about 1-65% of the low-melting a liquid herbicides, about 2-30% by weight of the alkaline white carbon, and about 0-90% of an agronomically acceptable adjuvant or mixture thereof.
4. The composition according to claim 2 which is characterized by about 0.5-5.0% of the sulfamoyl urea compound, about 5-30% of the low-melting or liquid herbicides, about 10-30% of the alkaline white carbon, and about 30-60% of an agronomically acceptable adjuvant or mixture thereof.
The composition according to claim 2 wherein the dinitroaniline herbicide is pendimethalin or trifluralin.
6. The composition according to claim 5 wherein the dinitroaniline herbicide is pendimethalin.
7. The composition according to claim 2 wherein the thiocarbamate herbicide is selected from the group consisting of esprocarb, benthiocarb, and molinate.
8. The composition according to claim 7 wherein the thiocarbamate herbicide is esprocarb.
9. The composition according to claim 2 wherein the chloroacetamide herbicide is selected from the group consisting of butachlor, pretilachlor, metolachlor and alachlor.
The composition according to claim 2 wherein the alkaline white carbon is selected from the group consisting of Carplex® #100 and Carplex@ #1120.
11. The composition according to claim 2 wherein the alkaline white carbon is an amorphous hydrous silicon dioxide.
12. A stable herbicidal composition substantially as hereinbefore described with reference to any one of the Examples. Dated 3 August, 1994 American Cyanamid Company 15 Patent Attorneys for the Applicant/Nominated Person SPRUSON FERGUSON s S. I S* o* *o* [N:\LIBW106033:GSA Stable Herbicidal Combination Compositions Abstract There is provided a stable herbicidal comnposition comprising 1 [o-(cyclopropylcarbonyl)-pheiiyl]sulfamoyl}-3-(4 ,6-di methioxy-2-pyri midiniyl)-urea H 3 C-O o H1 N NHN H 3 C-O Q in combination with one or more low-melting or liquid herbicides and alkaline white carbon. WWbI 07431:JC', t of i
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10741093A | 1993-08-16 | 1993-08-16 | |
| US107410 | 1993-08-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU7028294A AU7028294A (en) | 1995-02-23 |
| AU672121B2 true AU672121B2 (en) | 1996-09-19 |
Family
ID=22316526
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU70282/94A Ceased AU672121B2 (en) | 1993-08-16 | 1994-08-15 | Stable herbicidal combination compositions |
Country Status (5)
| Country | Link |
|---|---|
| KR (1) | KR100310959B1 (en) |
| AU (1) | AU672121B2 (en) |
| BR (1) | BR9403254A (en) |
| CO (1) | CO4340715A1 (en) |
| TW (1) | TW270881B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103783061A (en) * | 2014-02-27 | 2014-05-14 | 江苏省激素研究所股份有限公司 | Wheat-field compound herbicide containing metolachlor |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5009699A (en) * | 1990-06-22 | 1991-04-23 | American Cyanamid Company | 1-{[O-(cyclopropylcarbonyl)phenyl]sulfamoyl}-3-(4,6-dimethoxy-2-pyrimidinyl)urea herbicidal composition and use |
-
1994
- 1994-08-11 CO CO94035524A patent/CO4340715A1/en unknown
- 1994-08-13 KR KR1019940019996A patent/KR100310959B1/en not_active IP Right Cessation
- 1994-08-15 AU AU70282/94A patent/AU672121B2/en not_active Ceased
- 1994-08-16 BR BR9403254A patent/BR9403254A/en not_active IP Right Cessation
- 1994-12-10 TW TW083111509A patent/TW270881B/zh not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5009699A (en) * | 1990-06-22 | 1991-04-23 | American Cyanamid Company | 1-{[O-(cyclopropylcarbonyl)phenyl]sulfamoyl}-3-(4,6-dimethoxy-2-pyrimidinyl)urea herbicidal composition and use |
Also Published As
| Publication number | Publication date |
|---|---|
| KR100310959B1 (en) | 2002-11-13 |
| BR9403254A (en) | 1995-04-11 |
| AU7028294A (en) | 1995-02-23 |
| CO4340715A1 (en) | 1996-07-30 |
| TW270881B (en) | 1996-02-21 |
| KR950005161A (en) | 1995-03-20 |
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