USH750H - Herbicidal suspension concentrate - Google Patents
Herbicidal suspension concentrate Download PDFInfo
- Publication number
- USH750H USH750H US07/260,649 US26064988A USH750H US H750 H USH750 H US H750H US 26064988 A US26064988 A US 26064988A US H750 H USH750 H US H750H
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- US
- United States
- Prior art keywords
- oil
- weight
- parts
- suspension concentrate
- corn
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
Definitions
- the present invention relates to a herbicidal suspension concentrate comprising a specific sulfonamide compound(s) and/or a salt(s) thereof, a vegetable oil, and a surfactant at a specified ratio.
- This is a useful concentrate which can control a wide variety of harmful weeds without any phytotoxicity against corns when applied to corn fields.
- European Patent Laid-Open Nos. 232,067 and 237,292 both disclose that sulfonamide compounds and their salts, which are the active ingredients contained in the herbicidal suspension concentrate of the present invention, are useful as herbicides for application to corn fields. However, they fail to disclose that these compounds can be admixed with a vegetable oil and a surfactant, thereby to prepare a suspension concentrate.
- the present invention relates to a herbicidal suspension concentrate characterized by comprising from 0.5 to 20 parts by weight of at least one compound selected from among sulfonamide compounds represented by the general formula (I): ##STR2## (wherein X is a hydrogen atom, a chlorine atom, a bromine atom, a methyl group, or a difluoromethyl group) and their salts as an active ingredient, from 55 to 94.5 parts by weight of a vegetable oil, and from 5 to 25 parts by weight of a surfactant.
- sulfonamide compounds represented by the general formula (I): ##STR2## (wherein X is a hydrogen atom, a chlorine atom, a bromine atom, a methyl group, or a difluoromethyl group) and their salts as an active ingredient, from 55 to 94.5 parts by weight of a vegetable oil, and from 5 to 25 parts by weight of a surfactant.
- the suspension concentrate of the present invention when applied to a corn field, provides improved weeding effect against harmful weeds in general, and against gramineous weeds in particular, without any phytotoxicity against corns. As a result of this improvement, the spectra of the harmful weeds to be controlled are spread, and further the amount of the active ingredient compound to be used can be decreased.
- the sulfonamide compounds of the present invention represented by the general formula (I), and their salts are already known as herbicides for application to corn fields. In practical use of these compounds, however, it is still required to decrease the amount of the active ingredient compound to be used in view of the reduction of expenditure for weeding and the reduction of environmental contamination. While it is also required to control as perfectly as possible a variety of weeds differing in growth stage without any crop injury to corns.
- the authors of the present invention have found that use of a vegetable oil in the preparation of a suspension concentrate wherein the sulfonamide compound, represented by the general formula (I), or its salt is blended with the vegetable oil and a specific surfactant at a specific weight ratio can satisfy the requirements mentioned above when an aqueous diluted suspension prepared from the suspension concentrate is applied to a corn field. Namely they have found that use of the vegetable oil improves the weeding effect against broad spectra of the harmful weeds to be controlled without any phytotoxicity against corns and can decrease the amount of the active ingredient compound to be used, and that consequently reduction of environmental pollution can be expected.
- Examples of sulfonamide compounds which are represented by the general formula (I), and which therefore can be used in the present invention include N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3-dimethylaminocarbonyl-2-pyridinesulfonamide, N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-6-chloro-3-dimethylaminocarbonyl-2-pyridinesulfonamide, N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-6-bromo-3-dimethylaminocarbonyl-2-pyridinesulfonamide, N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3-dimethylaminocarbonyl-6-methyl-2-pyridinesulfonamide, and N-[(4,6-dimethoxypyrimidin-2-yl)amino
- salts of the above-mentioned sulfonamide compound include those of alkali metals such as sodium and potassium, those of alkali earth metals such as magnesium and calcium, and those of amines such as monomethylamine, dimethylamine and triethylamine, specific examples of which include sodium and monomethylamine salts of N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3-dimethylaminocarbonyl-2-pyridinesulfonamide, and dimethylamine salt of N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3-dimethylaminocarbonyl-6-methyl-2-pyridinesulfonamide.
- N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3-dimethylaminocarbonyl-2-pyridinesulfonamide and its salts are exemplified as preferred compounds.
- corn oil is particularly preferred.
- any surfactant may be used as long as it can emulsify the above-mentioned vegetable oils in water.
- surfactants include those of vegetable oil derivatives such as polyoxyethylene hydrogenated castor oil ether; nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene (propylene)fatty acid esters, sorbitan monooleate, and polyoxyethylene sorbitan monolaurate; and anionic surfactants such as sodium alkylarylsulfonates, sodium dialkylsuccinate sodium dialkylsulfosuccinates, polyoxyethylene alkylaryl ether sulfates, polyoxyethylene alkyl phosphates, polyoxyethylene alkylaryl phosphates, and sodium alkylnaphthalenesulfonates.
- vegetable oil derivatives such as polyoxyethylene hydrogenated castor oil ether
- nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene (propylene)fatty acid esters, sorbitan monooleate, and polyoxy
- a mixture of a surfactant of vegetable oil derivatives, a nonionic surfactant and an anionic surfactant is preferably used.
- the suspension concentrate of the present invention is prepared, for example, according to the following procedure.
- At least one compound selected from among the sulfonamide compounds represented by the aforementioned general formula (I) and their salts as an active ingredient compound(s) is uniformly mixed with a vegetable oil and a surfactant and the resulting mixture is ground in order to obtain a suspension concentrate.
- an active ingredient compound(s) preliminarily ground is merely mixed with a vegetable oil and a surfactant to obtain a suspension concentrate.
- a thixotropic material(s) such as a bentonite-alkylamine complex(es) and/or aerosil may be added in an amount of, for example, 1 to 3 weight % based on the total concentrate if necessary.
- the suitable blending weight ratio of the above-mentioned active ingredient compound(s), the vegetable oil and the surfactant, which are the main components composing the suspension concentrate of the present invention is in the ranges of from 0.5 to 20:from 55 to 94.5:from 5 to 25 respectively, and preferably from 2 to 6:from 77 to 90:from 8 to 17 respectively.
- the suitable amount of the suspension concentrate of the present invention to be used cannot be generically specified because it varies depending on various conditions. In general, however, it is in the range of from 0.05 to 50 g/a, preferably from 0.1 to 25 g/a, and more preferably from 0.1 to 2.5 g/a, in terms of the amount of the active ingredient compound.
- a suspension concentrate according to the present invention was prepared in substantially the same manner as in the above-mentioned Formulation Example 1 except that 82 parts by weight of corn oil was used instead of 84 parts by weight and 12 parts by weight of Sorpol 3815 (trade name of a mixture of a polyoxyethylene alkylaryl ether, polyoxyethylene hydrogenated castor oil ether, a fatty acid derivative, and a sodium dialkylsulfosuccinate manufactured by Toho Chemical Co., Ltd.) was used instead of 10 parts by weight of Sorpol 3747.
- Sorpol 3815 trade name of a mixture of a polyoxyethylene alkylaryl ether, polyoxyethylene hydrogenated castor oil ether, a fatty acid derivative, and a sodium dialkylsulfosuccinate manufactured by Toho Chemical Co., Ltd.
- a suspension concentrate according to the present invention was prepared using the above-mentioned components (1) to (4) in substantially the same manner as in the above-mentioned Formulation Example 1.
- a suspension concentrate according to the present invention is prepared using the above-mentioned components (1) to (4) in substantially the same manner as in the above-mentioned Formulation Example 1.
- a suspension concentrate according to the present invention is prepared using the above-mentioned components (1) to (4) in substantially the same manner as in the above-mentioned Formulation Example 1.
- 1/3,000 are (a) pots and 1/10,000 are (a) pots were filled with upland soil.
- Corn (Zea mays) (variety: Royal Dent 105 T) was sown in the 1/3,000 are (a) pots, while large crabgrass (Digitaria adscendens) and smartweed (Polygonum hydropiper) were separately sown in the 1/10,000 are (a) pots.
- Corns (Zea mays) (varieties: Royal Dent 105T and Golden cross vantum) were sown in 6 test plots, each 2 m 2 , and weeds were allowed to naturally grow therein.
- the growth stages of the plants 36 days after the sowing of corns were 4 to 6-leaf stages (a 5.2-leaf stage on the average) for Royal Dent 105T, 3 to 5.6-leaf stages (a 4.2-leaf stage on the average) for Golden cross vantum, 1 to 7-leaf stages (a 4.5-leaf stage on the average) for green foxtail (Setaria viridis), 1 to 6-leaf stages (a 4-leaf stage on the average) for large crabgrass (Digitaria adscendens), 2 to 6.5-leaf stages (a 4-leaf stage on the average) for smartweed (Polyonum hydropiper), cotyledon to 4-leaf stages (a 2-leaf stage on the average) for pigweed
- the average ratings for the degree of growth control evaluated for the two test runs were found to be 1 for both of the two varieties of corns as crops and 10 for all of green foxtail, large crabgrass, smartweed, pigweed, and cocklebur.
- 1/3,000 are (a) pots were filled with upland soil.
- Corn (Zea mays) variety: Royal Dent 105 T) and large crabgrass (Digitaria adscendens) were sown in the separate pots respectively, and grown under upland condition in a greenhouse.
- 5 liters/a each of aqueous diluted suspensions, prepared by suspending in water the suspension concentrate prepared in the aforementioned Formulation Example 3 were each separately foliarly applied to the plants with a small spray gun.
Abstract
A herbicidal suspension concentrate characterized by comprising from 0.5 to 20 parts by weight of at least one compound selected from among sulfonamide compounds represented by the general formula (I). ##STR1## (wherein X is a hydrogen atom, a chloride atom, a bromine atom, a methyl group, or a difluoromethyl group) and their salts as an active ingredient, from 55 to 94.5 parts by weight of a vegetable oil, and from 5 to 25 parts by weight of a surfactant.
Description
1. Field of the Invention
The present invention relates to a herbicidal suspension concentrate comprising a specific sulfonamide compound(s) and/or a salt(s) thereof, a vegetable oil, and a surfactant at a specified ratio. This is a useful concentrate which can control a wide variety of harmful weeds without any phytotoxicity against corns when applied to corn fields.
2. Description of the Related Art
European Patent Laid-Open Nos. 232,067 and 237,292 both disclose that sulfonamide compounds and their salts, which are the active ingredients contained in the herbicidal suspension concentrate of the present invention, are useful as herbicides for application to corn fields. However, they fail to disclose that these compounds can be admixed with a vegetable oil and a surfactant, thereby to prepare a suspension concentrate.
While, on the other hand, U.S. Pat. Nos. 3,997,322, No. 4,529,438, British Pat. No. 803,772, West German Pat. No. 2,701,129, Chemical and Engineering News, July 21, 1969, page 41, Japanese Patent Application No. 58-8232 (published on August 2, 1984 as publication No. KOKAI 59-134702) and Japanese Patent Application No. 58-242982 (published on July 16, 1985 as publication No. KOKAI 60-132904) all contain descriptions relating to the preparation of herbicidal compositions by mixing herbicidal compounds with vegetable oils, these prior art papers, however, fail to disclose that the specific sulfonamide compounds and their salts which are contained in the herbicidal suspension concentrate of the present invention can be used as herbicidal compounds.
The present invention relates to a herbicidal suspension concentrate characterized by comprising from 0.5 to 20 parts by weight of at least one compound selected from among sulfonamide compounds represented by the general formula (I): ##STR2## (wherein X is a hydrogen atom, a chlorine atom, a bromine atom, a methyl group, or a difluoromethyl group) and their salts as an active ingredient, from 55 to 94.5 parts by weight of a vegetable oil, and from 5 to 25 parts by weight of a surfactant.
The suspension concentrate of the present invention, when applied to a corn field, provides improved weeding effect against harmful weeds in general, and against gramineous weeds in particular, without any phytotoxicity against corns. As a result of this improvement, the spectra of the harmful weeds to be controlled are spread, and further the amount of the active ingredient compound to be used can be decreased.
As was mentioned previously, the sulfonamide compounds of the present invention, represented by the general formula (I), and their salts are already known as herbicides for application to corn fields. In practical use of these compounds, however, it is still required to decrease the amount of the active ingredient compound to be used in view of the reduction of expenditure for weeding and the reduction of environmental contamination. While it is also required to control as perfectly as possible a variety of weeds differing in growth stage without any crop injury to corns.
The authors of the present invention have found that use of a vegetable oil in the preparation of a suspension concentrate wherein the sulfonamide compound, represented by the general formula (I), or its salt is blended with the vegetable oil and a specific surfactant at a specific weight ratio can satisfy the requirements mentioned above when an aqueous diluted suspension prepared from the suspension concentrate is applied to a corn field. Namely they have found that use of the vegetable oil improves the weeding effect against broad spectra of the harmful weeds to be controlled without any phytotoxicity against corns and can decrease the amount of the active ingredient compound to be used, and that consequently reduction of environmental pollution can be expected.
Examples of sulfonamide compounds which are represented by the general formula (I), and which therefore can be used in the present invention, include N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3-dimethylaminocarbonyl-2-pyridinesulfonamide, N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-6-chloro-3-dimethylaminocarbonyl-2-pyridinesulfonamide, N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-6-bromo-3-dimethylaminocarbonyl-2-pyridinesulfonamide, N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3-dimethylaminocarbonyl-6-methyl-2-pyridinesulfonamide, and N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-6-difluoromethyl-3-dimethylaminocarbonyl-2-pyridine-sulfonamide.
Further, salts of the above-mentioned sulfonamide compound include those of alkali metals such as sodium and potassium, those of alkali earth metals such as magnesium and calcium, and those of amines such as monomethylamine, dimethylamine and triethylamine, specific examples of which include sodium and monomethylamine salts of N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3-dimethylaminocarbonyl-2-pyridinesulfonamide, and dimethylamine salt of N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3-dimethylaminocarbonyl-6-methyl-2-pyridinesulfonamide.
Among the above-mentioned sulfonamide compounds, N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3-dimethylaminocarbonyl-2-pyridinesulfonamide and its salts are exemplified as preferred compounds.
Examples of vegetable oils which can be used in the present invention include olive oil, kapok oil, castor oil, palm oil, camellia oil, coconut oil, sesame oil, corn oil, rice bran oil, peanut oil, cotton seed oil, soybean oil, rape seed oil, linseed oil, and tung oil. Among these vegetable oils, corn oil is particularly preferred.
In the present invention, any surfactant may be used as long as it can emulsify the above-mentioned vegetable oils in water.
Examples of such surfactants include those of vegetable oil derivatives such as polyoxyethylene hydrogenated castor oil ether; nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene (propylene)fatty acid esters, sorbitan monooleate, and polyoxyethylene sorbitan monolaurate; and anionic surfactants such as sodium alkylarylsulfonates, sodium dialkylsuccinate sodium dialkylsulfosuccinates, polyoxyethylene alkylaryl ether sulfates, polyoxyethylene alkyl phosphates, polyoxyethylene alkylaryl phosphates, and sodium alkylnaphthalenesulfonates.
Particularly, a mixture of a surfactant of vegetable oil derivatives, a nonionic surfactant and an anionic surfactant is preferably used.
The suspension concentrate of the present invention is prepared, for example, according to the following procedure.
At least one compound selected from among the sulfonamide compounds represented by the aforementioned general formula (I) and their salts as an active ingredient compound(s) is uniformly mixed with a vegetable oil and a surfactant and the resulting mixture is ground in order to obtain a suspension concentrate. Alternatively, such an active ingredient compound(s) preliminarily ground is merely mixed with a vegetable oil and a surfactant to obtain a suspension concentrate.
When consideration is given to the suspension stability of the active ingredient compound(s) in the suspension concentrate, a thixotropic material(s) such as a bentonite-alkylamine complex(es) and/or aerosil may be added in an amount of, for example, 1 to 3 weight % based on the total concentrate if necessary.
The suitable blending weight ratio of the above-mentioned active ingredient compound(s), the vegetable oil and the surfactant, which are the main components composing the suspension concentrate of the present invention, is in the ranges of from 0.5 to 20:from 55 to 94.5:from 5 to 25 respectively, and preferably from 2 to 6:from 77 to 90:from 8 to 17 respectively.
The suitable amount of the suspension concentrate of the present invention to be used, cannot be generically specified because it varies depending on various conditions. In general, however, it is in the range of from 0.05 to 50 g/a, preferably from 0.1 to 25 g/a, and more preferably from 0.1 to 2.5 g/a, in terms of the amount of the active ingredient compound.
In order to illustrate the present invention in more detail, description will now be made of Formulation Examples wherein the herbicidal suspension concentrates of the present invention were prepared and Test Examples wherein some of the prepared suspension concentrates were used, both of which, however, should not be construed as limiting the scope of the present invention.
__________________________________________________________________________
(1)
N--[(4,6-dimethoxypyrimidin-2-yl)aminocarbony1]-3-
dimethylaminocarbonyl-2-pyridinesulfonamide
5 parts by weight
(2)
corn oil 84
parts by weight
(3)
Sorpol 3747 (trade name of a mixture of a
polyoxyethylene alkylaryl ether, polyoxyethylene
hydrogenated castor oil ether, a polyoxyethylene
alkylaryl phosphate, a sodium dialkyl-
sulfosuccinate, and a fatty acid manufactured by
Toho Chemical Co., Ltd.) 10
parts by weight
(4)
bentonite-alkylamine complex
1 part by weight
__________________________________________________________________________
The above-mentioned components (1) to (4) were mixed uniformly and the resulting mixture was ground with a Dyno-Mill (manufactured by Willy A. Bachofen AG) to obtain a suspension concentrate according to the present invention.
A suspension concentrate according to the present invention was prepared in substantially the same manner as in the above-mentioned Formulation Example 1 except that 82 parts by weight of corn oil was used instead of 84 parts by weight and 12 parts by weight of Sorpol 3815 (trade name of a mixture of a polyoxyethylene alkylaryl ether, polyoxyethylene hydrogenated castor oil ether, a fatty acid derivative, and a sodium dialkylsulfosuccinate manufactured by Toho Chemical Co., Ltd.) was used instead of 10 parts by weight of Sorpol 3747.
__________________________________________________________________________
(1)
N--[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3-
dimethylaminocarbonyl-2-pyridinesulfonamide
5.06
parts by weight
(2)
corn oil, soybean oil, cotton seed oil, rape
seed oil or linseed oil 80.94
parts by weight
(3)
Sorpol 3815 12 parts by weight
(4)
bentonite-alkylamine complex
2 parts by weight
__________________________________________________________________________
A suspension concentrate according to the present invention was prepared using the above-mentioned components (1) to (4) in substantially the same manner as in the above-mentioned Formulation Example 1.
__________________________________________________________________________
(1)
N--[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3-
dimethylaminocarbonyl-2-pyridinesulfonamide
2 parts by weight
(2)
corn oil 85
parts by weight
(3)
Sorpol 3815 10
parts by weight
(4)
bentonite-alkylamine complex
3 parts by weight
__________________________________________________________________________
A suspension concentrate according to the present invention is prepared using the above-mentioned components (1) to (4) in substantially the same manner as in the above-mentioned Formulation Example 1.
__________________________________________________________________________
(1)
N--[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3-
dimethylaminocarbonyl-2-pyridinesulfonamide
6 parts by weight
(2)
corn oil 80
parts by weight
(3)
Sorpol 3747 13
parts by weight
(4)
bentonite-alkylamine complex
1 part by weight
__________________________________________________________________________
A suspension concentrate according to the present invention is prepared using the above-mentioned components (1) to (4) in substantially the same manner as in the above-mentioned Formulation Example 1.
1/3,000 are (a) pots and 1/10,000 are (a) pots were filled with upland soil. Corn (Zea mays) (variety: Royal Dent 105 T) was sown in the 1/3,000 are (a) pots, while large crabgrass (Digitaria adscendens) and smartweed (Polygonum hydropiper) were separately sown in the 1/10,000 are (a) pots. When the plants reached respective given growth stages (a 4-leaf stage for corn, a 3-leaf stage for large crabgrass, and a 1-leaf stage for smartweed), 5 liters/a each of aqueous diluted suspensions, prepared by suspending in water the suspension concentrate prepared in the aforementioned Formulation Example 2 so as to provide respective amounts of the active ingredient of 1.25 g/a and 0.625 g/a, were each separately foliarly applied to the plants with a small spray gun.
The progress of growth of the plants was visually observed and examined 29 days after the application to evaluate the degree of growth control according to 10 ratings (1: the same as in an untreated plot to 10: perfect growth control). The results are shown in Table 1.
For comparison, a test was made using substantially the same procedure as in the above-mentioned Test Example 1 except that use was made of individual comparative suspensions prepared by suspending the following wettable powder in water so as to provide respective amounts of its active ingredient of 1.25 g/a and 0.625 g/a and admixing 0.2 weight % of Shin Rino (trade name of a mixture of a polyethylene glycolalkylphenol ether and a lignonsulfonate manufactured by Nihon Nohyaku Co., Ltd.) with the respective resulting aqueous diluted suspensions. The results are shown in Table 1.
TABLE 1
______________________________________
Degree of Growth Control
large
corn 4L crabgrass 3L
smartweed 1L
Amount of Active Ingredient (g/a)
1.25 0.625 1.25 0.625 1.25 0.625
______________________________________
Plots Using
1 1 10 9 10 10
Present
Invention
Plots Using
1 1 9 6-7 10 10
Comparative
Suspension
______________________________________
(Note) The wettable powder used in the comparative plots is a mixture
composed of 40 parts by weight of
N--[(4,6dimethoxypyrimidin-2-yl)aminocarbonyl3-dimethylaminocarbonyl-2-py
idinesulfonamide, 8 parts by weight of Carplex #80 (trade name of syntheti
fine silica manufactured by Shionogi & Co., Ltd.), 46 parts by weight of
jeaklite, 4 parts by weight of Sorpol 5039 (trade name of a
polyoxyethylene alkylaryl ether sulfate manufactured by Toho Chemical Co.
Ltd.), and 2 parts by weight of Dikssol W92 (trade name of polyoxyethylen
octylphenyl ether manufactured by Daiichi Kogyo Seiyaku Co., Ltd.).
Corns (Zea mays) (varieties: Royal Dent 105T and Golden cross vantum) were sown in 6 test plots, each 2 m2, and weeds were allowed to naturally grow therein. The growth stages of the plants 36 days after the sowing of corns were 4 to 6-leaf stages (a 5.2-leaf stage on the average) for Royal Dent 105T, 3 to 5.6-leaf stages (a 4.2-leaf stage on the average) for Golden cross vantum, 1 to 7-leaf stages (a 4.5-leaf stage on the average) for green foxtail (Setaria viridis), 1 to 6-leaf stages (a 4-leaf stage on the average) for large crabgrass (Digitaria adscendens), 2 to 6.5-leaf stages (a 4-leaf stage on the average) for smartweed (Polyonum hydropiper), cotyledon to 4-leaf stages (a 2-leaf stage on the average) for pigweed (Amaranthus retroflexus), and cotyledon to 4.2-leaf stages (a 3-leaf stage on the average) for cocklebur (Xanthium strumarium). Thirty six days after the sowing of corns, 8 liters/a each of aqueous diluted suspensions prepared by suspending in water the suspension concentrate prepared in the aforementioned Formulation Example 3 (corn oil was used as a vegetable oil) so as to provide respective amounts of the active ingredient of 1.25 g/a and 0.75 g/a were foliarly applied to the plants with a manual knap-sack type sprayer. The foregoing test was repeated.
The progress of growth of the plants was visually observed and examined 45 days after the application evaluate the degree of growth control according to the same ratings as in the aforementioned Test Example 1.
The average ratings for the degree of growth control evaluated for the two test runs were found to be 1 for both of the two varieties of corns as crops and 10 for all of green foxtail, large crabgrass, smartweed, pigweed, and cocklebur.
1/3,000 are (a) pots were filled with upland soil. Corn (Zea mays) (variety: Royal Dent 105 T) and large crabgrass (Digitaria adscendens) were sown in the separate pots respectively, and grown under upland condition in a greenhouse. When the plants reached respective given growth stages (a 4.8-leaf stage for corn and a 3.5-leaf stage for large crabgrass), 5 liters/a each of aqueous diluted suspensions, prepared by suspending in water the suspension concentrate prepared in the aforementioned Formulation Example 3, were each separately foliarly applied to the plants with a small spray gun.
The progress of growth of the plants was visually observed and examined 28 days after the application to evaluate the degree of growth control according to the same ratings as in the aforementioned Test Example 1. The results are shown in Table 2.
For comparison, a test was made according to substantially the same procedure as in the abovementioned Test Example 3 using the same wettable powder applied for the comparative plots in the aforementioned Test Example 1.
TABLE 2
______________________________________
Degree of Growth Control
large
corn 4.8L crabgrass 3.5L
Amount of Active Ingredient
(g/a)
Vegetable Oil Used
1 0.5 0.25 1 0.5 0.25
______________________________________
Corn Oil
Plots Using Present
1 1 1 9-10 9 6
Invention
Soybean Oil
Plots Using Present
1 1 1 10 9-10 6
Invention
Cotton Seed Oil
Plots Using Present
1 1 1 9-10 9 7
Invention
Rape Seed Oil
Plots Using Present
1 1 1 9-10 9 7-8
Invention
Linseed Oil
Plots Using Present
1 1 1 10 9 6
Invention
None
Plots Using Compara-
1 1 1 4 3 2
tive Suspension
______________________________________
Claims (4)
1. A herbicidal suspension concentrate characterized by comprising from 0.5 to 20 parts by weight of at least one compound selected from among sulfonamide compounds represented by the general formula (I): ##STR3## wherein X is a hydrogen atom, a chlorine atom, a bromine atom, a methyl group, or a difluoromethyl group and their salts as an active ingredient; from 55 to 94.5 parts by weight of a vegetable oil, and from 5 to 25 parts by weight of a surfactant.
2. A herbicidal suspension concentrate as claimed in claim 1, wherein the vegetable oil is at least one selected from the group consisting of olive oil, kapok oil, castor oil, palm oil, camellia oil, coconut oil, sesame oil, corn oil, rice bran oil, peanut oil, cotton seed oil, soybean oil, rape seed oil, linseed oil and tung oil.
3. A herbicidal suspension concentrate as claimed in claim 1, wherein the weight ratio of the sulfonamide compound represented by the general formula (I) or its salt, the vegetable oil and the surfactant is in the ranges of from 2 to 6:from 77 to 90:from 8 to 17, respectively.
4. A herbicidal suspension concentrate as claimed in claim 1, wherein the suspension concentrate comprises from 0.5 to 20 parts by weight of N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3-dimethylaminocarbonyl-2-pyridinesulfonamide or its salt, from 55 to 94.5 parts by weight of corn oil, and from 5 to 25 parts by weight of a mixture of surfactants.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62-267548 | 1987-10-22 | ||
| JP62267548A JP2569342B2 (en) | 1987-10-22 | 1987-10-22 | Herbicidal suspension composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| USH750H true USH750H (en) | 1990-03-06 |
Family
ID=17446344
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US07/260,649 Abandoned USH750H (en) | 1987-10-22 | 1988-10-21 | Herbicidal suspension concentrate |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | USH750H (en) |
| EP (1) | EP0313317B1 (en) |
| JP (1) | JP2569342B2 (en) |
| KR (1) | KR930006675B1 (en) |
| CN (1) | CN1025812C (en) |
| AR (1) | AR246023A1 (en) |
| AU (1) | AU2396888A (en) |
| BR (1) | BR8805441A (en) |
| DE (1) | DE3870396D1 (en) |
| ES (1) | ES2031605T3 (en) |
| GR (1) | GR3005151T3 (en) |
| HU (1) | HU203829B (en) |
| PL (1) | PL275421A1 (en) |
| ZA (1) | ZA887894B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110021350A1 (en) * | 2007-03-08 | 2011-01-27 | E.I. Du Pont De Nemours And Company | Liquid sulfonylurea herbicide formulations |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0456198A1 (en) * | 1990-05-10 | 1991-11-13 | Hodogaya Chemical Co., Ltd. | Oil suspension concentrate for direct paddy water application |
| US5206372A (en) * | 1990-06-05 | 1993-04-27 | Shell Research Limited | Preparation of 2-chloropyridine derivatives |
| DE69300089T2 (en) * | 1992-01-28 | 1995-07-20 | Ishihara Sangyo Kaisha | Chemically stabilized herbicidal oil-based suspension. |
| ES2123033T3 (en) * | 1992-11-18 | 1999-01-01 | Ishihara Sangyo Kaisha | METHOD TO INCREASE HERBICIDE ACTIVITY, HERBICIDE COMPOSITION WITH INCREASED ACTIVITY AND COMPOSITION TO INCREASE ACTIVITY. |
| AU653299B2 (en) * | 1993-02-06 | 1994-09-22 | Nihon Nohyaku Co., Ltd. | A herbicidal composition having a reduced phytotoxicity |
| CA2280513C (en) | 1997-02-05 | 2007-05-22 | Basf Aktiengesellschaft | Sulphonylurea and/adjuvant based solid mixtures |
| CA2284198C (en) | 1997-03-24 | 2007-11-27 | Basf Aktiengesellschaft | Solid mixtures based sulfonylurea and adjuvants |
| PT1130962E (en) * | 1998-09-25 | 2004-04-30 | Basf Ag | CONCENTRATED IN NON-AQUEOUS SUSPENSION |
| US6165940A (en) * | 1998-09-25 | 2000-12-26 | American Cyanamid Co. | Non-aqueous suspension concentrate |
| DE19951427A1 (en) * | 1999-10-26 | 2001-05-17 | Aventis Cropscience Gmbh | Non-aqueous or low-water suspension concentrates of active ingredient mixtures for crop protection |
| JP2003512398A (en) * | 1999-10-26 | 2003-04-02 | アベンティス・クロップサイエンス・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | Herbicide |
| WO2001055562A1 (en) * | 2000-01-25 | 2001-08-02 | Mitsubishi Denki Kabushiki Kaisha | Valve timing adjusting device |
| TWI243019B (en) * | 2000-08-31 | 2005-11-11 | Basf Ag | Process for the preparation of a solid herbicidal formulation |
| DOP2001000246A (en) | 2000-09-13 | 2002-09-15 | Basf Ag | OLEOUS SUSPENSIONS CONCENTRATED BASED ON A CYCLHEXENONOXIMETER LITHIUM SALT AND ITS USE AS PHYTOSANITARY PRODUCTS |
| DE10129855A1 (en) * | 2001-06-21 | 2003-01-02 | Bayer Ag | Suspension concentrates based on oil |
| EA012031B1 (en) * | 2002-12-13 | 2009-06-30 | Байер Кропсайенс Аг | Herbicidal oil suspension concentrate, |
| PL1651042T3 (en) | 2003-07-25 | 2016-09-30 | Herbicidal composition having the herbicidal effect enhanced, and method for enhancing the herbicidal effect | |
| JP4629379B2 (en) * | 2003-07-25 | 2011-02-09 | 石原産業株式会社 | Herbicidal composition with improved herbicidal efficacy and method for improving herbicidal efficacy |
| DE10334301A1 (en) | 2003-07-28 | 2005-03-03 | Bayer Cropscience Gmbh | Liquid formulation |
| DE10334300A1 (en) * | 2003-07-28 | 2005-03-03 | Bayer Cropscience Gmbh | Oil suspension concentrate |
| DE102004011007A1 (en) | 2004-03-06 | 2005-09-22 | Bayer Cropscience Ag | Suspension concentrates based on oil |
| NZ563883A (en) * | 2005-06-04 | 2011-02-25 | Bayer Cropscience Ag | Oil suspension concentrate comprising dioxazine pyridylsulfonylureas |
| CN100418418C (en) * | 2005-06-24 | 2008-09-17 | 福建省泉州德盛农药有限公司 | Pesticide auxiliary agent |
| ZA200802442B (en) | 2005-09-01 | 2010-02-24 | Du Pont | Liquid sulfonylurea herbicide formulations |
| JP5122841B2 (en) * | 2006-03-24 | 2013-01-16 | 石原産業株式会社 | Herbicidal composition |
| RU2562946C2 (en) | 2010-04-26 | 2015-09-10 | ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи | Stabilised agricultural oil dispersions |
| FR2967361A1 (en) * | 2010-11-16 | 2012-05-18 | Rhodia Operations | OILY DISPERSIONS OF SOLID COMPOUNDS CONTAINING PHOSPHATE ESTERS |
| GB2496643B (en) * | 2011-11-17 | 2016-08-17 | Rotam Agrochem Int Co Ltd | Herbicidal suspension concentrate |
| MX363109B (en) | 2012-05-25 | 2019-03-08 | Bayer Cropscience Ag | Chemical stabilization of iodosulfuron-methyl sodium salt by hydroxystearates. |
| EP3481196A4 (en) * | 2016-07-06 | 2020-01-29 | Crop Enhancement, Inc. | Nontoxic coating concentrates for agricultural uses |
| CN108124858B (en) * | 2018-01-18 | 2021-05-07 | 乔欣 | Coconut oil auxiliary agent and preparation method and application thereof |
| WO2021146155A1 (en) * | 2020-01-14 | 2021-07-22 | Crop Enhancement, Inc. | Nontoxic coating concentrates for agricultural uses |
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| GB803772A (en) | 1954-08-03 | 1958-10-29 | Edwin Denis Clifford Baptist | Improvements in systemic herbicide compositions |
| US3997322A (en) | 1970-09-09 | 1976-12-14 | Sun Oil Company Of Pennsylvania | Herbicide carrier oil composition |
| DE2701129A1 (en) | 1977-01-13 | 1978-07-20 | Knut Heyn | Oil-based compsn. for use with herbicides - reducing the requirement of the latter and promoting rapid absorption by plants |
| US4529438A (en) | 1982-03-23 | 1985-07-16 | Zoecon Corp. | Pyridyloxy-phenoxy-alkanoic acid esters and derivatives |
| EP0232067A3 (en) | 1986-01-30 | 1988-03-30 | Ishihara Sangyo Kaisha Ltd. | Substituted pyridinesulfonamide compounds, herbicidal composition containing them, and method of preparing these compounds |
| EP0237292A3 (en) | 1986-03-07 | 1988-05-18 | E.I. Du Pont De Nemours And Company | Herbicidal pyridine sulfonamides |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59134702A (en) * | 1983-01-21 | 1984-08-02 | Ishihara Sangyo Kaisha Ltd | Emulsifying herbicide composition |
| JPS6130585A (en) * | 1984-07-23 | 1986-02-12 | Ishihara Sangyo Kaisha Ltd | Substituted pyridinesulfonamide compound and herbicide containing it |
| JPH01110604A (en) * | 1987-10-21 | 1989-04-27 | Ishihara Sangyo Kaisha Ltd | Control of harmful weed |
| JPH06130585A (en) * | 1992-10-20 | 1994-05-13 | Fuji Photo Film Co Ltd | Photographic black-and-white developing composition and method for procesing silver halide photographic sensitive material |
-
1987
- 1987-10-22 JP JP62267548A patent/JP2569342B2/en not_active Expired - Lifetime
-
1988
- 1988-10-18 AU AU23968/88A patent/AU2396888A/en not_active Abandoned
- 1988-10-19 DE DE8888309772T patent/DE3870396D1/en not_active Expired - Lifetime
- 1988-10-19 EP EP88309772A patent/EP0313317B1/en not_active Expired - Lifetime
- 1988-10-19 ES ES198888309772T patent/ES2031605T3/en not_active Expired - Lifetime
- 1988-10-21 BR BR8805441A patent/BR8805441A/en not_active IP Right Cessation
- 1988-10-21 US US07/260,649 patent/USH750H/en not_active Abandoned
- 1988-10-21 ZA ZA887894A patent/ZA887894B/en unknown
- 1988-10-21 HU HU885439A patent/HU203829B/en unknown
- 1988-10-21 KR KR1019880013750A patent/KR930006675B1/en not_active IP Right Cessation
- 1988-10-21 AR AR88312273A patent/AR246023A1/en active
- 1988-10-21 CN CN88107260A patent/CN1025812C/en not_active Expired - Lifetime
- 1988-10-21 PL PL27542188A patent/PL275421A1/en unknown
-
1992
- 1992-07-13 GR GR920401494T patent/GR3005151T3/el unknown
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB803772A (en) | 1954-08-03 | 1958-10-29 | Edwin Denis Clifford Baptist | Improvements in systemic herbicide compositions |
| US3997322A (en) | 1970-09-09 | 1976-12-14 | Sun Oil Company Of Pennsylvania | Herbicide carrier oil composition |
| DE2701129A1 (en) | 1977-01-13 | 1978-07-20 | Knut Heyn | Oil-based compsn. for use with herbicides - reducing the requirement of the latter and promoting rapid absorption by plants |
| US4529438A (en) | 1982-03-23 | 1985-07-16 | Zoecon Corp. | Pyridyloxy-phenoxy-alkanoic acid esters and derivatives |
| EP0232067A3 (en) | 1986-01-30 | 1988-03-30 | Ishihara Sangyo Kaisha Ltd. | Substituted pyridinesulfonamide compounds, herbicidal composition containing them, and method of preparing these compounds |
| EP0237292A3 (en) | 1986-03-07 | 1988-05-18 | E.I. Du Pont De Nemours And Company | Herbicidal pyridine sulfonamides |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110021350A1 (en) * | 2007-03-08 | 2011-01-27 | E.I. Du Pont De Nemours And Company | Liquid sulfonylurea herbicide formulations |
Also Published As
| Publication number | Publication date |
|---|---|
| GR3005151T3 (en) | 1993-05-24 |
| HU203829B (en) | 1991-10-28 |
| EP0313317B1 (en) | 1992-04-22 |
| EP0313317A3 (en) | 1990-01-17 |
| AU2396888A (en) | 1989-04-27 |
| PL275421A1 (en) | 1989-07-10 |
| ZA887894B (en) | 1989-07-26 |
| EP0313317A2 (en) | 1989-04-26 |
| BR8805441A (en) | 1989-06-27 |
| KR890006619A (en) | 1989-06-14 |
| ES2031605T3 (en) | 1992-12-16 |
| CN1032729A (en) | 1989-05-10 |
| JPH01110605A (en) | 1989-04-27 |
| KR930006675B1 (en) | 1993-07-22 |
| JP2569342B2 (en) | 1997-01-08 |
| CN1025812C (en) | 1994-09-07 |
| DE3870396D1 (en) | 1992-05-27 |
| AR246023A1 (en) | 1994-03-30 |
| HUT49446A (en) | 1989-10-30 |
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Owner name: ISHIHARA SANGYO KAISHA LTD., JAPAN Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:OGAWA, YASUO;KIMURA, FUMIO;KIMURA, AKIRA;AND OTHERS;SIGNING DATES FROM 19880928 TO 19880929;REEL/FRAME:004965/0449 |
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