CA1040642A - Substituted oxirane compounds - Google Patents
Substituted oxirane compoundsInfo
- Publication number
- CA1040642A CA1040642A CA225,754A CA225754A CA1040642A CA 1040642 A CA1040642 A CA 1040642A CA 225754 A CA225754 A CA 225754A CA 1040642 A CA1040642 A CA 1040642A
- Authority
- CA
- Canada
- Prior art keywords
- oxirane
- active ingredients
- chloro
- trichloroethyl
- sodium
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/08—Compounds containing oxirane rings with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Epoxy Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
ABSTRACT
This invention concerns novel substituted oxirane compounds which correspond to the formula.
This invention concerns novel substituted oxirane compounds which correspond to the formula.
Description
1040~i4Z
The present invention concerns substituted oxirane compounds corresponding to the formula:
/o\
CH2 ~ CH2CC12X
~01 ~\R
(I) wherein X is hydrogen, chloro or methyl; each R group independently represents bromo, chloro, fluoro, C1 3 alkyl, trifluoromethyl, nitro, or Cl 3 alkoxy; and R represents hydrogen, bromo, chloro, fluoro, Cl 3 alkyl, trifluoromethyl, nitro, or Cl 3 alkoxy.
The compounds of the above Formula I, here-inafter referred for convenience as "active ingredi-ents", have been found to be uniquely active as herbi-cides for the control of undesired vegetation. Aa-cordingly, the present invention also encompasses compositions containing one or more active ingredients as well as methods of controlling undesired plant growth.
Such methods comprise applying one or more active ingredients to the locus of the undesired plants, that ; 25 is, the seeds, foliage or other parts of the growing plants or soil in which the plants are growing or would grow.
The term "alkyl" as used herein and in the appended claims is employed to designate the radicals methyl, ethyl, propyl, and isopropyl. Similarly, the .~
'',251-F -1-.: ., '' ~, . :.
: - , :.. ~ ~ , :. ' . ' ' term "alkoxy" is employed to mean the radicals methoxy, ethoxy, propoxy, and isopropoxy. The term "herbicide"
is used herein to mean an active ingredient which controls or modifies the growth of plants.
The active ingredients of the present inven-tion are generally oils or crystalline solids at ambient temperatures which are soluble in many organic solvents commonly employed as herbicidal carriers. The active ingredients of the above Formula I wherein X is chloro constitute a preferred embodiment of the present inven-tion. Active ingredients wherein Rl is hydrogen and ` each R group is the same constitute a further preferred emhodiment. Another preferred embodiment of the present invention includes active ingredients wherein each R group is bromo, chloro or fluoro. In still another embodiment of the present invention, active ingredients ~
; wherein each R group is alkyl are preferred. In a -further preferred embodiment, each R and Rl is bromo, chloro, or Cl 3 alkyl.
The active ingredients of the above Formula - -I are readily prepared by the reaction of a substituted styrene compound of the formula:
` CH ;~--CH2CC12X
~ ~ ~
R Rl R
(II) 1,251-F -2-- : . ... . . ..
: ' . '' - , ' ' : ' .
wherein X, R and Rl are as previously defined, with a suitable carboxylic acid reactant. Representative and suitable carboxylic acids which can be employed in the preparation of the active ingredients include, for example, chloracetic acid, trifluoroacetic acid, and percarboxylic acids such as perbenzoic acid or peracetic acid. In the present invention, buffer solutions of the acid reactants are preferably employed and are prepared by the use of a buffer agent, such as, for example, sodium acetate, or sodium benzoate.
In carrying out the reaction, the substituted styrene reactant of Formula II is usually mixed with a reaction medium, such as, for example, methylene chloride, chloroform, or 1,2-dichlorobenzene, and mixed slowly with the percarboxylic acid reactant in a buffer solution. While the amounts of the reactants 3 to be employed are not critical, the reaction generally consumes reactants in the proportion of 1 mole of substituted styrene reactant to one or more moles of acid reactant. A suitable ratio of reactants is from 1 to 1 to 1 to 6 (substituted styrene:acid) and the employment of the reactant in a mole ratio of from 1 to 3 moles preferred. The reaction is usually con-ducted at temperatures between 20 and 40C. and is ordinarily carried out at ambient atmospheric pressure.
The resulting reaction mixture is usually maintained, with stirring, for a period of time sufficient to provide for substantial completion of the reaction.
Generally, the reaction mixture is stirred at ambient temperatures for a period of from 24 to 100 hours or i7,251-F -3-: . .: . . . .
. . .
.
more. Recovery of the desired product from the reaction mixture is achieved by employin~ conventional procedures.
Typically, the reaction mass is washed with water and neutralized with a sufficient amount of a base, e.gr, sodium carbonate or the like, before being concentrated to dryness ur~der sub-atmospheric pressure.
The substituted styrene reactants of Formula II and the acids employed as starting materials in the preparation of the active ingredients of the pres-ent invention are known and are readily available or can be easily prepared by those skilled in the art according to known methods or methods analagous thereto.
The compounds of the present invention have been found to be suitable for use in methods for the pre- and post-emergent control of weeds or other unwanted vegetation. Certain of the active ingredients of the --present invention have been found to be active against undesired vegetation in the presence of desired crop plants while giving little or no herbicidal action on the crop plants. For all such uses, unmodified active ingredients of the present invention can be employed.
However, the present invention embraces the use of a herbicidally-effective amount of the active ingredi-ents in composition form with an inert carrier material in solid or liquid form. Thus, for example, an active ingredient can be dispersed on a finely divided solid and employed therein as a dust. Also, the active ingredients, as liquid concentrates or solid composi-tions comprising one or more of the active ingredients, can be dispersed in water, typically with the aid of 17,251-F ~4-. ' ' ~ ' ' , :
' ''. ' 104~642 a wetting agent, and the resulting aqueous dispersion employed as a spray. In other procedures, the active ingredient can be employed as a constituent of organic li~uid compositions, oil-in-water and water in-oil emulsions, or water dispersions, with or without the addition of wetting, dispersing, or emulsifying agents.
As organic solvents used as extending agents there can be employed hydrocarbons, e.g. benzene, toluene, xylene, kerosene, diesel fuel, fuel oil, and petroleum naphtha; ketones such as acetone, methyl ethyl ketone, or cyclohexanone; chlorinated hydrocarbons such as carbon tetrachloride, chloroform, trichloro-ethylene, or perchloroethylene; esters such as ethyl acetate, amyl acetate, or butyl acetate; ethers, e.g., ethylene glycol monomethyl ether and diethylene glycol monomethyl ether; alcohols, e.g., methanol, ethanol, isopropanol, amyl alcohol, ethylene glycol, propylene glycol, and glycerine. Mixtures of water and organic solvents, either as solutions or emulsions, can be employed.
The active ingredients can also be applied as aerosols, e.g., by dispersing them by means of a compressed gas such as dichlorodifluoromethane or trichlorofluoromethane.
The active ingredients of the present invention can also be applied with solid adjuvants or carriers such as talc, pyrophyllite, synthetic fine silica, attapulgus clay, kieselguhr, chalk, diatomaceous earth, - lime, calcium carbonate, bentonite, fuller's earth, c~ttonseed hulls, wheat flour, soybean flour, pumice, 17,251-F -5--.
. .
1(~4064Z
tripoli, wood flour, walnut shell flour, redwood flour, or lignin.
As stated, it is frequently desirable to incorporate a surface active agent in the compositions of the present invention. Such surface active or wetting agents are advantageously employed in both the solid and liquid compositions. The surface active agent can be anionic, cationic or nonionic in character.
Typical classes of surface active agents include alkyl sulfonate salts, alkylaryl sulfonate salts, alkylaryl polyether alcohols, fatty acid esters of polyhydric alcohols and the alkylene oxide addition products of such esters, and addition products of long chain mercaptans and alkylene oxides. Typical examples of such surface active agents include the sodium alkyl-benzene sulfonates having 10 to 18 carbon atoms in the alkyl group, alkylphenol-ethylene oxide condensation products, e.g., p-isooctylphenol condensed with 10 ethylene oxide units, soaps, e.g., sodium stearate and potassium oleate, sodium salt of propylnaphthalene sulfonic acid, di(2-ethylhexyl)ester of sodium sulfo-succinic acid, sodium lauryl sulfate, sodium decane-sulfonate, sodium salt of the sulfonated monoglyceride ~ ~ -- of coconut fatty acids, sorbitan sesquioleate, lauryl trimethyl ammonium chloride, octadecyl trimethyl ammonium chloride, polyethylene glycol lauryl ether, polyethylene glycol esters of fatty acids and rosin acids, sodium N-methyl-N-oleyl taurate, Turkey Red Oil, sodium di~utyl naphthalene sulfonate, sodium lignin sulfonate, poly-ethylene glycol stearate, tertiary dodecyl polyethylene ': ' 17,251~ -6-'' . ; .;~ : .
.
. .
, ~04V642 glycol thioether, long chain ethylene oxide-propylene oxide condensation products, e.g., molecular weight 1000, polyethylene glycol ester of tall oil acids, sodium octyl phenoxyethoxyethyl sulfate, tris(poly-oxyethylene)-sorbitan monostearate, and sodium di-hexyl sulfosuccinate.
The concentration of the active ingredients in solid or liquid compositions generally is from 0.003 to 95 percent by weight. Concentrations of from 0.003 to 50 weight percent are often employedr In composi-tions to be employed as concentrates, the active in-gredient can be present in a concentration of from 5 to 98 weight percent. The active ingredient com-positions can also contain other compatible additaments, for example, phytotoxicants, plant growth regulants, and pesticides, and can be formulated with solid par-ticulate fertilizer carriers such as ammonium nitrate or urea.
The present compositions can be applied by the use of power-dusters, boom and hand sprayers, spray-dusters, by addition to irrigation water, and by other conventional means. The compositions can also be applied from airplanes as a dust or a spray since certain of the active ingredients are effective at low application rates.
Certain active ingredients of the present invention have been found to possess particularly unique and desirable herbicidal activity against certain Setaria species, especially Setaria viridis (Green Foxtail) and especially in pre-emergence operations.
?7,251-F -7-11)4064Z
Such unique herbicidal activity is obtained at various low, economical application rates without endangering one or more of certain desirable crop species, such as, for example, cotton, corn, sorghum or soybeans.
Selection of the 3,5-substituted and 3,4,5-substituted active ingredients, particularly the 3,5-substituted active ingredients, is apparently a critical factor in obtaining control of Green Foxtail in the presence of certain desirable crop species since certain related compounds have been found to be definitely inferior for such use to the active ingredients of the present invention. The active ingredients of the present invention which possess selective toxicity to Green Foxtail are therefore particularly useful in herbicidal mixtures, making up for deficiencies of other herbi-cides, yet not endangering desirable crop species. ;
~ The exact rate to be applied is dependent ; not only upon the specific active ingredient being employed, but also upon the particular action desired (e.g., general or selective control), the plant species to be modified and the stage of growth thereof as well ` as the part of the plant to be contacted with the toxic active ingredient. Thus, all of the active ingredients ; of the invention and compositions containing the same may not be equally effective at similar concentrations or against the same plant species. In non-selective pre-emergence and foliage treatments, the active in-gredients of this invention are usually applied at an approximate rate of from 1 to 25 lbs. per acre, (1.12-27.8 kg./hectare), but lower or higher rates 17,251-F -8-~, 1~)4064Z
may be appro~riate in some cases. In selective pre-and post-emergence operations, a dosage of from 0.13 to 1.0 pounds per acre tO.145-1.12 kg./hectare) is usually employed, but higher dosages may be necessary in some instances. One skilled in the art can readily determine the optimum rate to be applied in any par-ticular case.
In an illustrative representative operation, an aqueous composition containing 2-(3,5-dichlorophenyl)-
The present invention concerns substituted oxirane compounds corresponding to the formula:
/o\
CH2 ~ CH2CC12X
~01 ~\R
(I) wherein X is hydrogen, chloro or methyl; each R group independently represents bromo, chloro, fluoro, C1 3 alkyl, trifluoromethyl, nitro, or Cl 3 alkoxy; and R represents hydrogen, bromo, chloro, fluoro, Cl 3 alkyl, trifluoromethyl, nitro, or Cl 3 alkoxy.
The compounds of the above Formula I, here-inafter referred for convenience as "active ingredi-ents", have been found to be uniquely active as herbi-cides for the control of undesired vegetation. Aa-cordingly, the present invention also encompasses compositions containing one or more active ingredients as well as methods of controlling undesired plant growth.
Such methods comprise applying one or more active ingredients to the locus of the undesired plants, that ; 25 is, the seeds, foliage or other parts of the growing plants or soil in which the plants are growing or would grow.
The term "alkyl" as used herein and in the appended claims is employed to designate the radicals methyl, ethyl, propyl, and isopropyl. Similarly, the .~
'',251-F -1-.: ., '' ~, . :.
: - , :.. ~ ~ , :. ' . ' ' term "alkoxy" is employed to mean the radicals methoxy, ethoxy, propoxy, and isopropoxy. The term "herbicide"
is used herein to mean an active ingredient which controls or modifies the growth of plants.
The active ingredients of the present inven-tion are generally oils or crystalline solids at ambient temperatures which are soluble in many organic solvents commonly employed as herbicidal carriers. The active ingredients of the above Formula I wherein X is chloro constitute a preferred embodiment of the present inven-tion. Active ingredients wherein Rl is hydrogen and ` each R group is the same constitute a further preferred emhodiment. Another preferred embodiment of the present invention includes active ingredients wherein each R group is bromo, chloro or fluoro. In still another embodiment of the present invention, active ingredients ~
; wherein each R group is alkyl are preferred. In a -further preferred embodiment, each R and Rl is bromo, chloro, or Cl 3 alkyl.
The active ingredients of the above Formula - -I are readily prepared by the reaction of a substituted styrene compound of the formula:
` CH ;~--CH2CC12X
~ ~ ~
R Rl R
(II) 1,251-F -2-- : . ... . . ..
: ' . '' - , ' ' : ' .
wherein X, R and Rl are as previously defined, with a suitable carboxylic acid reactant. Representative and suitable carboxylic acids which can be employed in the preparation of the active ingredients include, for example, chloracetic acid, trifluoroacetic acid, and percarboxylic acids such as perbenzoic acid or peracetic acid. In the present invention, buffer solutions of the acid reactants are preferably employed and are prepared by the use of a buffer agent, such as, for example, sodium acetate, or sodium benzoate.
In carrying out the reaction, the substituted styrene reactant of Formula II is usually mixed with a reaction medium, such as, for example, methylene chloride, chloroform, or 1,2-dichlorobenzene, and mixed slowly with the percarboxylic acid reactant in a buffer solution. While the amounts of the reactants 3 to be employed are not critical, the reaction generally consumes reactants in the proportion of 1 mole of substituted styrene reactant to one or more moles of acid reactant. A suitable ratio of reactants is from 1 to 1 to 1 to 6 (substituted styrene:acid) and the employment of the reactant in a mole ratio of from 1 to 3 moles preferred. The reaction is usually con-ducted at temperatures between 20 and 40C. and is ordinarily carried out at ambient atmospheric pressure.
The resulting reaction mixture is usually maintained, with stirring, for a period of time sufficient to provide for substantial completion of the reaction.
Generally, the reaction mixture is stirred at ambient temperatures for a period of from 24 to 100 hours or i7,251-F -3-: . .: . . . .
. . .
.
more. Recovery of the desired product from the reaction mixture is achieved by employin~ conventional procedures.
Typically, the reaction mass is washed with water and neutralized with a sufficient amount of a base, e.gr, sodium carbonate or the like, before being concentrated to dryness ur~der sub-atmospheric pressure.
The substituted styrene reactants of Formula II and the acids employed as starting materials in the preparation of the active ingredients of the pres-ent invention are known and are readily available or can be easily prepared by those skilled in the art according to known methods or methods analagous thereto.
The compounds of the present invention have been found to be suitable for use in methods for the pre- and post-emergent control of weeds or other unwanted vegetation. Certain of the active ingredients of the --present invention have been found to be active against undesired vegetation in the presence of desired crop plants while giving little or no herbicidal action on the crop plants. For all such uses, unmodified active ingredients of the present invention can be employed.
However, the present invention embraces the use of a herbicidally-effective amount of the active ingredi-ents in composition form with an inert carrier material in solid or liquid form. Thus, for example, an active ingredient can be dispersed on a finely divided solid and employed therein as a dust. Also, the active ingredients, as liquid concentrates or solid composi-tions comprising one or more of the active ingredients, can be dispersed in water, typically with the aid of 17,251-F ~4-. ' ' ~ ' ' , :
' ''. ' 104~642 a wetting agent, and the resulting aqueous dispersion employed as a spray. In other procedures, the active ingredient can be employed as a constituent of organic li~uid compositions, oil-in-water and water in-oil emulsions, or water dispersions, with or without the addition of wetting, dispersing, or emulsifying agents.
As organic solvents used as extending agents there can be employed hydrocarbons, e.g. benzene, toluene, xylene, kerosene, diesel fuel, fuel oil, and petroleum naphtha; ketones such as acetone, methyl ethyl ketone, or cyclohexanone; chlorinated hydrocarbons such as carbon tetrachloride, chloroform, trichloro-ethylene, or perchloroethylene; esters such as ethyl acetate, amyl acetate, or butyl acetate; ethers, e.g., ethylene glycol monomethyl ether and diethylene glycol monomethyl ether; alcohols, e.g., methanol, ethanol, isopropanol, amyl alcohol, ethylene glycol, propylene glycol, and glycerine. Mixtures of water and organic solvents, either as solutions or emulsions, can be employed.
The active ingredients can also be applied as aerosols, e.g., by dispersing them by means of a compressed gas such as dichlorodifluoromethane or trichlorofluoromethane.
The active ingredients of the present invention can also be applied with solid adjuvants or carriers such as talc, pyrophyllite, synthetic fine silica, attapulgus clay, kieselguhr, chalk, diatomaceous earth, - lime, calcium carbonate, bentonite, fuller's earth, c~ttonseed hulls, wheat flour, soybean flour, pumice, 17,251-F -5--.
. .
1(~4064Z
tripoli, wood flour, walnut shell flour, redwood flour, or lignin.
As stated, it is frequently desirable to incorporate a surface active agent in the compositions of the present invention. Such surface active or wetting agents are advantageously employed in both the solid and liquid compositions. The surface active agent can be anionic, cationic or nonionic in character.
Typical classes of surface active agents include alkyl sulfonate salts, alkylaryl sulfonate salts, alkylaryl polyether alcohols, fatty acid esters of polyhydric alcohols and the alkylene oxide addition products of such esters, and addition products of long chain mercaptans and alkylene oxides. Typical examples of such surface active agents include the sodium alkyl-benzene sulfonates having 10 to 18 carbon atoms in the alkyl group, alkylphenol-ethylene oxide condensation products, e.g., p-isooctylphenol condensed with 10 ethylene oxide units, soaps, e.g., sodium stearate and potassium oleate, sodium salt of propylnaphthalene sulfonic acid, di(2-ethylhexyl)ester of sodium sulfo-succinic acid, sodium lauryl sulfate, sodium decane-sulfonate, sodium salt of the sulfonated monoglyceride ~ ~ -- of coconut fatty acids, sorbitan sesquioleate, lauryl trimethyl ammonium chloride, octadecyl trimethyl ammonium chloride, polyethylene glycol lauryl ether, polyethylene glycol esters of fatty acids and rosin acids, sodium N-methyl-N-oleyl taurate, Turkey Red Oil, sodium di~utyl naphthalene sulfonate, sodium lignin sulfonate, poly-ethylene glycol stearate, tertiary dodecyl polyethylene ': ' 17,251~ -6-'' . ; .;~ : .
.
. .
, ~04V642 glycol thioether, long chain ethylene oxide-propylene oxide condensation products, e.g., molecular weight 1000, polyethylene glycol ester of tall oil acids, sodium octyl phenoxyethoxyethyl sulfate, tris(poly-oxyethylene)-sorbitan monostearate, and sodium di-hexyl sulfosuccinate.
The concentration of the active ingredients in solid or liquid compositions generally is from 0.003 to 95 percent by weight. Concentrations of from 0.003 to 50 weight percent are often employedr In composi-tions to be employed as concentrates, the active in-gredient can be present in a concentration of from 5 to 98 weight percent. The active ingredient com-positions can also contain other compatible additaments, for example, phytotoxicants, plant growth regulants, and pesticides, and can be formulated with solid par-ticulate fertilizer carriers such as ammonium nitrate or urea.
The present compositions can be applied by the use of power-dusters, boom and hand sprayers, spray-dusters, by addition to irrigation water, and by other conventional means. The compositions can also be applied from airplanes as a dust or a spray since certain of the active ingredients are effective at low application rates.
Certain active ingredients of the present invention have been found to possess particularly unique and desirable herbicidal activity against certain Setaria species, especially Setaria viridis (Green Foxtail) and especially in pre-emergence operations.
?7,251-F -7-11)4064Z
Such unique herbicidal activity is obtained at various low, economical application rates without endangering one or more of certain desirable crop species, such as, for example, cotton, corn, sorghum or soybeans.
Selection of the 3,5-substituted and 3,4,5-substituted active ingredients, particularly the 3,5-substituted active ingredients, is apparently a critical factor in obtaining control of Green Foxtail in the presence of certain desirable crop species since certain related compounds have been found to be definitely inferior for such use to the active ingredients of the present invention. The active ingredients of the present invention which possess selective toxicity to Green Foxtail are therefore particularly useful in herbicidal mixtures, making up for deficiencies of other herbi-cides, yet not endangering desirable crop species. ;
~ The exact rate to be applied is dependent ; not only upon the specific active ingredient being employed, but also upon the particular action desired (e.g., general or selective control), the plant species to be modified and the stage of growth thereof as well ` as the part of the plant to be contacted with the toxic active ingredient. Thus, all of the active ingredients ; of the invention and compositions containing the same may not be equally effective at similar concentrations or against the same plant species. In non-selective pre-emergence and foliage treatments, the active in-gredients of this invention are usually applied at an approximate rate of from 1 to 25 lbs. per acre, (1.12-27.8 kg./hectare), but lower or higher rates 17,251-F -8-~, 1~)4064Z
may be appro~riate in some cases. In selective pre-and post-emergence operations, a dosage of from 0.13 to 1.0 pounds per acre tO.145-1.12 kg./hectare) is usually employed, but higher dosages may be necessary in some instances. One skilled in the art can readily determine the optimum rate to be applied in any par-ticular case.
In an illustrative representative operation, an aqueous composition containing 2-(3,5-dichlorophenyl)-
-2-(2,2,2-trichloroethyl)oxirane is prepared by mixing four parts by weight of the compound, 0.08 part by weight of sorbitan trioleate, and 0.02 part of a sor-bitan monooleate polyoxyethylene derivative in about 40 ml. of acetone. A portion of this concentrate ~-composition is separately dispersed in a portion of water to provide an aqueous composition containing about O.44 pound of the active ingredient per 100 gal-lons (0.5 g./liter of ultimate treating composition.
The composition was applied to seedbeds previously seeded with cotton and green foxtail and the treated seeds covered with a thin layer of soil.
Application of the treating composition was made at a rate sufficient to provide about one pound per acre (1.12 kg./hectare) of the active test ingredient. There-after, the treated seedbeds as well as untreated control ; seedbeds were held under conditions conducive to growth for a period of about two weeks and then examined.
In the treated seedbeds, it was found that there was a thriving stand of cotton seedlings; but no Green Foxtail seedlings were evident. In the control seedbeds, 17,251-F ~9~
: , . ' ~4~)6~Z
observation showed thriving stands of both cotton and green foxtail seedlings.
Similar selective results in the presence o one or more desirable crops as hereinbefore mentioned are also obtained with other active ingredients of the present invention at various application rates.
The following example illustrates the present invention.
Exam~le 1 2-(3,5-Dichlorophenyl)-4,4,4-trichloro-1-butene (39.7 grams; 0.13 mole) was mixed with 225 milliliters (ml.) of methylene chloride. A solution of 40% peracetic acid (74 grams; 0.39 mole) in 5.3 grams of sodium acetate trihydrate was then added dropwise to the butene reac-tant solution. During the addition of the peracetic acid solution, the temperature of the reaction mixture rose from 23 to 28C. The resulting reaction mixture was maintained, with stirring, for about 100 hours ~ -at ambient temperatures. Following this period, the reaction mixture was washed with three 200-milliliter portions of a 10~ sodium carbonate solution. The organic product layer was separated and washed with 100 milliliters of water and then dried over anhydrous sodium sulfate. The organic product layer was then reduced in vacuo~ The resulting yellow re~idue was mixed with 230 ml. of methylene chlorida and the re-sulting mixture washed with two 100-millilitar portions of a 10~ sodium carbonate solution. The organic product layer was separated therefrom and dried over sodium sulfate and again reduced in vacuo at 30C~ and at 7,251-F -10-.
1t)4V64Z
0.1 millimeter of mercury. 2-(3,5-Dichlorophenyl)--2-(2,2,2-trichloroethyl)oxirane was recovered as a yellow oil having a refractive index n25 = 1.5720.
Infrared and nuclear magnetic reasonance spectra were consistent with the assigned structure.
Other active ingredients of the present invention are similarly prepared by employing procedures analogous to that in the above example.
Such other active ingredients include, inter alia, the following:
2-(3,5-Bis(trifluoromethyl)phenyl)-2-(2,2,2-tri-chloroethyl)oxirane, a light yellow oil having a refrac-tive index n25 = 1.4654; 2-(3,5-dimethylphenyl)-2--(2,2,2-trichloroethyl)oxirane, a light yellow oil having a refractive index n25 = 1.5441; 2-(3,5-diethyl-phenyl)-2-(2,2,2-trichloroethyl)oxirane, a yello~
oil having a refractive index n25 = 1.5335; 2-(2,2- --dichloroethyl)-2-(3,5-dimethylphenyl)oxirane, a yellow oil having a refractive index nD5 = 1.53337 2-(3-bromo-5-methylphe~yl)-2-(2,2,2-trichloroethyl)oxirane, a yellow oil having a refractive index n25 = 1.5635; 2-(2,2--dichloropropyl)-2-~3,5-dimethoxyphenyl)oxirane; 2-(2,2--dichloroethyl)-2-(3,5-dinitrophenyl)oxirane; 2-(2,2--dichloropropyl)-2-(3,5-bis(trifluoromethyl)phenyl)-oxirane; 2-t5-chloro-3-methylphenyl)-2-(2,2,2-trichloro-ethyl)oxirane; 2-(2,2,2-dichloroethyl)-2-[3-chloro-5--(trifluoromethyl)phellyl]oxirane; 2-(3-bromo-5-nitrophenyl)--2-(2,2,2-trichloroethyl)oxirane; 2-(2,2-dichloropropyl)--2-15 methyl-3-nitrophenyl)oxirane; 2-(3-methoxy-5--nitrophenyl)-2-(2,2,2-trichloroethyl)oxirane;
17,251-F -11-' . ~
:
.
, lr~4~)~4z 2-(3-methyl-5-ethoxyphenyl)-2-(2,2,2-trichloroethyl)-oxirane, 2-(5-chloro-3-isopropoxyphenyl)-2-(2,2-di-chloroethyl)oxirane, 2-(3,4,5-trichlorophenyl)-2--(2,2,2-trichloroethyl)oxirane; 2-(3,4,5-tribromo-phenyl)-2-t2,2-dichloropropyl)oxirane; 2-(3,5-dichloro--4-methylphenyl)-2-(2,2-dichloroethyl)oxirane; 2-(3,5- .
-difluorophenyl)-2-(2,2,2-trichloroethyl)oxirane; 2--(3,4,5-trinitrophenyl)-2-(2,2,2-trichloroethyl)oxirane;
2-[4-chloro-3,5-bis(trifluoromethyl)phenyl]-2-(2,2--dichloropropyl)oxirane; 2-(2,2-dichloroethyl)-2-(3,4,5--trimethoxyphenyl)oxirane; 2-(2,2-dichloroethyl)-2-(3,5--difluoro-4-nitrophenyl)oxirane; 2-(4-chloro-3,5-diiso-propoxyphenyl)-2-(2,2,2-trichloroethyl)oxirane; 2-(2,2,2--trichloroethyl~-2-(3,4,5-triethylphenyl)oxirane; 2-(3,5--dimethyl-4-trifluoromethylphenyl)-2-(2,2,2-trichloroethyl)-oxirane; 2-(3-fluorophenyl)-2-(2,2,2-trichloroethyl)-o~irane; and 2-(3-fluoro-5-methylphenyl)-2-(2,2,2--trichloroethyl)oxirane.
L7,251-F -12-
The composition was applied to seedbeds previously seeded with cotton and green foxtail and the treated seeds covered with a thin layer of soil.
Application of the treating composition was made at a rate sufficient to provide about one pound per acre (1.12 kg./hectare) of the active test ingredient. There-after, the treated seedbeds as well as untreated control ; seedbeds were held under conditions conducive to growth for a period of about two weeks and then examined.
In the treated seedbeds, it was found that there was a thriving stand of cotton seedlings; but no Green Foxtail seedlings were evident. In the control seedbeds, 17,251-F ~9~
: , . ' ~4~)6~Z
observation showed thriving stands of both cotton and green foxtail seedlings.
Similar selective results in the presence o one or more desirable crops as hereinbefore mentioned are also obtained with other active ingredients of the present invention at various application rates.
The following example illustrates the present invention.
Exam~le 1 2-(3,5-Dichlorophenyl)-4,4,4-trichloro-1-butene (39.7 grams; 0.13 mole) was mixed with 225 milliliters (ml.) of methylene chloride. A solution of 40% peracetic acid (74 grams; 0.39 mole) in 5.3 grams of sodium acetate trihydrate was then added dropwise to the butene reac-tant solution. During the addition of the peracetic acid solution, the temperature of the reaction mixture rose from 23 to 28C. The resulting reaction mixture was maintained, with stirring, for about 100 hours ~ -at ambient temperatures. Following this period, the reaction mixture was washed with three 200-milliliter portions of a 10~ sodium carbonate solution. The organic product layer was separated and washed with 100 milliliters of water and then dried over anhydrous sodium sulfate. The organic product layer was then reduced in vacuo~ The resulting yellow re~idue was mixed with 230 ml. of methylene chlorida and the re-sulting mixture washed with two 100-millilitar portions of a 10~ sodium carbonate solution. The organic product layer was separated therefrom and dried over sodium sulfate and again reduced in vacuo at 30C~ and at 7,251-F -10-.
1t)4V64Z
0.1 millimeter of mercury. 2-(3,5-Dichlorophenyl)--2-(2,2,2-trichloroethyl)oxirane was recovered as a yellow oil having a refractive index n25 = 1.5720.
Infrared and nuclear magnetic reasonance spectra were consistent with the assigned structure.
Other active ingredients of the present invention are similarly prepared by employing procedures analogous to that in the above example.
Such other active ingredients include, inter alia, the following:
2-(3,5-Bis(trifluoromethyl)phenyl)-2-(2,2,2-tri-chloroethyl)oxirane, a light yellow oil having a refrac-tive index n25 = 1.4654; 2-(3,5-dimethylphenyl)-2--(2,2,2-trichloroethyl)oxirane, a light yellow oil having a refractive index n25 = 1.5441; 2-(3,5-diethyl-phenyl)-2-(2,2,2-trichloroethyl)oxirane, a yello~
oil having a refractive index n25 = 1.5335; 2-(2,2- --dichloroethyl)-2-(3,5-dimethylphenyl)oxirane, a yellow oil having a refractive index nD5 = 1.53337 2-(3-bromo-5-methylphe~yl)-2-(2,2,2-trichloroethyl)oxirane, a yellow oil having a refractive index n25 = 1.5635; 2-(2,2--dichloropropyl)-2-~3,5-dimethoxyphenyl)oxirane; 2-(2,2--dichloroethyl)-2-(3,5-dinitrophenyl)oxirane; 2-(2,2--dichloropropyl)-2-(3,5-bis(trifluoromethyl)phenyl)-oxirane; 2-t5-chloro-3-methylphenyl)-2-(2,2,2-trichloro-ethyl)oxirane; 2-(2,2,2-dichloroethyl)-2-[3-chloro-5--(trifluoromethyl)phellyl]oxirane; 2-(3-bromo-5-nitrophenyl)--2-(2,2,2-trichloroethyl)oxirane; 2-(2,2-dichloropropyl)--2-15 methyl-3-nitrophenyl)oxirane; 2-(3-methoxy-5--nitrophenyl)-2-(2,2,2-trichloroethyl)oxirane;
17,251-F -11-' . ~
:
.
, lr~4~)~4z 2-(3-methyl-5-ethoxyphenyl)-2-(2,2,2-trichloroethyl)-oxirane, 2-(5-chloro-3-isopropoxyphenyl)-2-(2,2-di-chloroethyl)oxirane, 2-(3,4,5-trichlorophenyl)-2--(2,2,2-trichloroethyl)oxirane; 2-(3,4,5-tribromo-phenyl)-2-t2,2-dichloropropyl)oxirane; 2-(3,5-dichloro--4-methylphenyl)-2-(2,2-dichloroethyl)oxirane; 2-(3,5- .
-difluorophenyl)-2-(2,2,2-trichloroethyl)oxirane; 2--(3,4,5-trinitrophenyl)-2-(2,2,2-trichloroethyl)oxirane;
2-[4-chloro-3,5-bis(trifluoromethyl)phenyl]-2-(2,2--dichloropropyl)oxirane; 2-(2,2-dichloroethyl)-2-(3,4,5--trimethoxyphenyl)oxirane; 2-(2,2-dichloroethyl)-2-(3,5--difluoro-4-nitrophenyl)oxirane; 2-(4-chloro-3,5-diiso-propoxyphenyl)-2-(2,2,2-trichloroethyl)oxirane; 2-(2,2,2--trichloroethyl~-2-(3,4,5-triethylphenyl)oxirane; 2-(3,5--dimethyl-4-trifluoromethylphenyl)-2-(2,2,2-trichloroethyl)-oxirane; 2-(3-fluorophenyl)-2-(2,2,2-trichloroethyl)-o~irane; and 2-(3-fluoro-5-methylphenyl)-2-(2,2,2--trichloroethyl)oxirane.
L7,251-F -12-
Claims (7)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A substituted oxirane compound corresponding to the formula wherein X is hydrogen, chloro, or methyl; each R independ-ently represents bromo, chloro, fluoro, C1-3 alkyl, tri-fluoromethyl, nitro, or C1-3 alkoxy; and R1 represents hydrogen, bromo, chloro, fluoro, C1-3 alkyl, trifluoro-methyl, nitro, or C1-3 alkoxy.
2. 2-(3,5-Dichlorophenyl)-2-(2,2,2-trichloro-ethyl)oxirane.
3. 2-[3,5-Bis(trifluoromethyl)phenyl]-2-(2,2,2--trichloroethyl)oxirane.
4. 2-(3,5-Dimethylphenyl)-2-(2,2,2-trichloro-ethyl)oxirane.
5. 2-(3,5-Diethylphenyl)-2-(2,2,2-trichloro-ethyl)oxirane.
6. 2-(2,2-Dichloroethyl)-2-(3,5-dimethylphenyl)-oxirane.
7. 2-(3-Bromo-5-methylphenyl)-2-(2,2,2-trichloro-ethyl)oxirane.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US46656774A | 1974-05-03 | 1974-05-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1040642A true CA1040642A (en) | 1978-10-17 |
Family
ID=23852259
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA225,754A Expired CA1040642A (en) | 1974-05-03 | 1975-04-29 | Substituted oxirane compounds |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS5337409B2 (en) |
| AR (1) | AR209300A1 (en) |
| BE (1) | BE828587A (en) |
| BR (1) | BR7502633A (en) |
| CA (1) | CA1040642A (en) |
| CS (1) | CS181782B2 (en) |
| ES (1) | ES437117A1 (en) |
| FR (1) | FR2269528B1 (en) |
| GB (1) | GB1469741A (en) |
| HU (1) | HU174284B (en) |
| IL (1) | IL47201A (en) |
| IT (1) | IT1050291B (en) |
| MY (1) | MY7800023A (en) |
| NL (1) | NL182879C (en) |
| SU (1) | SU626697A3 (en) |
| ZA (1) | ZA752820B (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4266964A (en) | 1979-04-30 | 1981-05-12 | The Dow Chemical Company | Herbicide antidote compounds and method of use |
| JPS5644311U (en) * | 1979-09-14 | 1981-04-22 | ||
| JPS631480Y2 (en) * | 1981-05-21 | 1988-01-14 | ||
| EP0101168B1 (en) * | 1982-07-13 | 1987-10-07 | Schering Agrochemicals Limited | Herbicidal mixtures |
| AU6004099A (en) * | 1998-10-07 | 2000-04-26 | Mitsubishi Chemical Corporation | Mixtures of optical isomers of 1,2-disubstituted-2,3-epoxypropanes, process for producing the same, pesticides containing the same as the active ingredient and intermediates thereof |
| KR101197482B1 (en) * | 2004-03-05 | 2012-11-09 | 닛산 가가쿠 고교 가부시키 가이샤 | Isoxazoline-Substituted Benzamide Compound And Noxious Organism Control Agent |
-
1975
- 1975-04-28 ES ES437117A patent/ES437117A1/en not_active Expired
- 1975-04-28 NL NLAANVRAGE7505024,A patent/NL182879C/en not_active IP Right Cessation
- 1975-04-29 IL IL47201A patent/IL47201A/en unknown
- 1975-04-29 IT IT49360/75A patent/IT1050291B/en active
- 1975-04-29 CA CA225,754A patent/CA1040642A/en not_active Expired
- 1975-04-30 CS CS7500003022A patent/CS181782B2/en unknown
- 1975-04-30 BE BE155949A patent/BE828587A/en not_active IP Right Cessation
- 1975-04-30 HU HU75DO394A patent/HU174284B/en not_active IP Right Cessation
- 1975-04-30 AR AR258593A patent/AR209300A1/en active
- 1975-04-30 FR FR7513631A patent/FR2269528B1/fr not_active Expired
- 1975-04-30 BR BR3345/75A patent/BR7502633A/en unknown
- 1975-04-30 JP JP5244675A patent/JPS5337409B2/ja not_active Expired
- 1975-04-30 SU SU752135951A patent/SU626697A3/en active
- 1975-05-01 ZA ZA00752820A patent/ZA752820B/en unknown
- 1975-05-01 GB GB1828675A patent/GB1469741A/en not_active Expired
-
1978
- 1978-12-30 MY MY23/78A patent/MY7800023A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2519073A1 (en) | 1975-11-20 |
| ZA752820B (en) | 1976-07-28 |
| GB1469741A (en) | 1977-04-06 |
| AU8061475A (en) | 1976-11-04 |
| SU626697A3 (en) | 1978-09-30 |
| IL47201A0 (en) | 1975-06-25 |
| HU174284B (en) | 1979-12-28 |
| AR209300A1 (en) | 1977-04-15 |
| IT1050291B (en) | 1981-03-10 |
| IL47201A (en) | 1978-08-31 |
| BE828587A (en) | 1975-10-30 |
| FR2269528A1 (en) | 1975-11-28 |
| CS181782B2 (en) | 1978-03-31 |
| MY7800023A (en) | 1978-12-31 |
| BR7502633A (en) | 1976-03-16 |
| FR2269528B1 (en) | 1977-07-08 |
| NL182879C (en) | 1988-06-01 |
| DE2519073B2 (en) | 1977-07-14 |
| JPS50148525A (en) | 1975-11-28 |
| NL7505024A (en) | 1975-11-05 |
| JPS5337409B2 (en) | 1978-10-09 |
| ES437117A1 (en) | 1977-04-16 |
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