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.

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• Life Sciences & Earth Sciences (AREA)
• Health & Medical Sciences (AREA)
• Organic Chemistry (AREA)
• Agronomy & Crop Science (AREA)
• Pest Control & Pesticides (AREA)
• Plant Pathology (AREA)
• Chemical & Material 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)

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Citations (6)

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• 1987
  • 1987-10-22 JP JP62267548A patent/JP2569342B2/ja not_active Expired - Lifetime
• 1988
  • 1988-10-18 AU AU23968/88A patent/AU2396888A/en not_active Abandoned
  • 1988-10-19 DE DE8888309772T patent/DE3870396D1/de not_active Expired - Lifetime
  • 1988-10-19 ES ES198888309772T patent/ES2031605T3/es not_active Expired - Lifetime
  • 1988-10-19 EP EP88309772A patent/EP0313317B1/en not_active Expired - Lifetime
  • 1988-10-21 CN CN88107260A patent/CN1025812C/zh not_active Expired - Lifetime
  • 1988-10-21 KR KR1019880013750A patent/KR930006675B1/ko not_active IP Right Cessation
  • 1988-10-21 PL PL27542188A patent/PL275421A1/xx unknown
  • 1988-10-21 HU HU885439A patent/HU203829B/hu unknown
  • 1988-10-21 BR BR8805441A patent/BR8805441A/pt not_active IP Right Cessation
  • 1988-10-21 ZA ZA887894A patent/ZA887894B/xx unknown
  • 1988-10-21 AR AR88312273A patent/AR246023A1/es active
  • 1988-10-21 US US07/260,649 patent/USH750H/en not_active Abandoned
• 1992
  • 1992-07-13 GR GR920401494T patent/GR3005151T3/el unknown

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Non-Patent Citations (1)

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