CA1043355A - Halophenoxy benzamide herbicides - Google Patents
Halophenoxy benzamide herbicidesInfo
- Publication number
- CA1043355A CA1043355A CA191,956A CA191956A CA1043355A CA 1043355 A CA1043355 A CA 1043355A CA 191956 A CA191956 A CA 191956A CA 1043355 A CA1043355 A CA 1043355A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- benzamide
- nitro
- plants
- sec
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/59—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
ADSTRACT OF THE DISCLOSURE
2-Nitro-5-(halophenoxy)benzoic acids and esters, salts, amides, and acyl halides thereof comprise a class of compounds that are highly effective pre- and post-emergence herbicides.
2-Nitro-5-(halophenoxy)benzoic acids and esters, salts, amides, and acyl halides thereof comprise a class of compounds that are highly effective pre- and post-emergence herbicides.
Description
~433SS
Background o ~he Invention Field of the Invention This invention is concerned with certain phenoxy-benzoic acid compounds and their use as herbicides.
Description of the Prior Art It has been proposed to use as herbicides 2-methoxy-benzoic acids (U.S. Patent 3,013,054) and 4-phenoxybenzoic acids (French Patent 1,502,538). It is the discovery of this invention, however, that benzoic acids having a phenoxy sub-stituent in the 5-position are very effective herbicides.
Summary of the Invention We have found that halophenoxy-benzamides of the formula:
COR
Background o ~he Invention Field of the Invention This invention is concerned with certain phenoxy-benzoic acid compounds and their use as herbicides.
Description of the Prior Art It has been proposed to use as herbicides 2-methoxy-benzoic acids (U.S. Patent 3,013,054) and 4-phenoxybenzoic acids (French Patent 1,502,538). It is the discovery of this invention, however, that benzoic acids having a phenoxy sub-stituent in the 5-position are very effective herbicides.
Summary of the Invention We have found that halophenoxy-benzamides of the formula:
COR
2~ ~ ~ (X)n wherein X is halogen, n is an integer of from l to 5, and R
is an alkylamino group containing 4 to 6 carbon atoms, or a dialkylamino group in which the alkyl groups contain 4 to 6 carbon atoms, have herbicidal activity~ When n is 2 or more, more than one halogen species may be substituted in the ben-zene ring of the phenoxy group, that is the X's need not all be the same and, for example, both fluoro and chloro sub-stituents may be present in the same compound; reference to X
being halogen is to be understood in this sense.
The compounds of the above formula are novel and constitute one aspect of the present invention.
The present invention also comprises a herbicidal 16~43;~SS
composition comprising a compound according to the invention and a carrier therefor.
The compounds of this invention are readily prepared by the Ullmann ether synthesis reaction between an alkali metal (e.g., Na or K) salt of~a halophenol and a 5-halo (e.g., Cl or Br) -2-nitrobenzamide. The latter can readily be pre-pared from the corresponding 5-halo-2-nitrobenzoic acid which in turn can be readily prepared by nitrating an m-halotoluene, followed by oxidation of the methyl group by well known procedures. Alternatively~ and in most cases preferably, the Ullmann ether synthesis is carried out using the corresponding benzoic acid or benzoic acid ester, such as the methyl ester, and in the latter case the ether formed is hydrolyzed to obtain the benzoic acid. The product obtained in either case, that is the halophenoxy-nitro-benzoic acid, is then converted into the desired benzamide by any convenient procedure, preferably by converting the benzoic acid to the corresponding benzoyl chloride and reacting the latter with the appropriate alkylamine or dialkylamine to obtain the desired benzamide.
Compounds according to the invention include, for example:
N-sec-butyl-2-nitro-5-(2',4'-dichloro-6'-fluoro-phenoxy)-benzamide, N,N-di-sec-butyl-2-nitro-5-(2',4'-dichloro-6'-fluorophenoxy)-benzamide, N-hexyl-2-nitro-5-(2',4'-dichloro-6'-fluorophenoxy)-benzamide, and ~-sec-butyl-2-nitro-5-(2',4',6'-trichlorophenoxy)-benzamide.
~)43355 In order that the invention may be more fully understood, the following preparative examples are given by way of illustration only:
Example 1 Methyl-2-nitro-5-(2',4'-dichloro-6'-fluorophenoxy)-benzoate is hydrolyzed to the acid by heating a 10 percent solution of the methyl ester with a 5 percent solution of sodium hydroxide at 70C for 8 to 10 hours until a clear solution is obtained. The excess alkali is neutralized with HCl and the free benzoic acid filtered off.
The acid is then dissolved in benzene and refluxed for 5 to 7 hours with 20 percent excess thionyl chloride.
me solvent and thionyl chloride are stripped off after reaction i8 complete.
The benzoyl chloride is then dissolved in benzene and sec-butylamine added. Reaction takes place immediately with evolution of HCl. The mixture is refluxed for 2 hours to completion. The solvent is then stripped off to give the product, N-sec-butyl-2-nitro-5-(2',4'-dichloro-6'-fluoro-phenoxy)-benzamide which is then recrystallized from a mix-ture of ether and petroleum ether.
Example 2 Example 1 is repeated, but using di-sec-butylamine instead of sec-butylamine, to give N,N-di-sec-butyl-2-nitro--5-(2',4'-dichloro-6'-fluorophenoxy)-benzamide.
Example 3 Bxample 1 is repeated, but using hexylamine as the amine, to give N-hexyl-2-nitro-5-(2',4'-dichloro-6'-fluoro-phenoxy)-benzamide.
~ . ,, ~ .
Example 4 Example 1 is repeated, but starting with methyl-2--nitro-5-(2',4',6'-trichlorophenoxy)-benzoate, to give N-sec--butyl-2-nitro-5-(2',4',6'-trichlorophenoxy)-benzamide.
-.
_ 4 -.;
The compounds of this invention can be applied in various ways to achieve herbicidal action. They can be applied, per se, as solids or in vaporized form, but are preferably applied as the toxic components in pesticidal compositions of the compound and a carrier. The compositions can be applied, as dusts;
as liquid sprays, or as gas-propelled sprays and can contain, in addition to a carrier, additives such as emulsifying agents, binding agents, gases compressed to the liquid state, odorants, stabilizers, and the like. A wide variety of liquid and solid carriers can be used. Non-limiting examples of solid carriers include talc, bentonite, diatomaceous earth, pyrophyllite, fullers earth, gypsum, flours derived from cotton seeds and nut shells, and various natural and synthetic clays having a pH not exceed-ing about 9.5. Non-limiting examples of liquid carriers, include water; organic solvents, such as alcohols, ketones, amides and esters; mineral oils, such as kerosene, light oils, and medium oils and vegetable oils, such as cottonseed oil.
In practice, herbicidal application is measured in terms of pounds of herbicide applied per acre. The compounds of this invention are effective herbicides when applied in herbicidal amounts, i.e., at rates between about 0.2 pounds and about 10 pounds per acre.
HERBICIDAL EFFECTIVENESS
Method of Propagating Test Species Crabgress Digitaria Sanguinalis Yellow Foxtail Grass Setaria glauca Johnson grass Sorgum Halepense Barnyard grass Echinochloa crus-galli Amaranth pigweed Amaranthus retroflexus Turnip Brassica sp.
Cotton Gossypium hirsutum var. DPL
oth leaf Corn Zea Mays var. Golden Bantam Bean Phaseolus vulgaris var.
Black Valentine All crop and weed species are planted individually in 3" plastic pots containing potting soil. Four seeds of each of corn, cotton, and snapbeans are seeded to a depth equal to the diameter of the seed. All other species are surface seeded and sprinkled with screened soil in an amount sufficient to cover the seeds. Immediately after planting, all pots are watered by sub-irrigation in greenhouse trays. Pots for the pre-emergence phase are seeded one day before treatment.
1~43355 Planting dates for the post-emergence phase are varied so that all the seedlings will reach the desired stage of development simultaneously. The proper stage of seedling development for treatment in the post-emergence phase is as follows:
GRASSES: 2 inches in height PIGWEED & TURNIPS: 1 or 2 true leaves visible above cotyledons.
COTTON: first true leaf 1 inch in length; expanded cotyledons.
CORN: 3 inches - 4 inches in height BEANS: primary leaves expanded, grow-ing point at primary leaf node.
Method of Treatment Spray applications are made in a hood containing a movable belt and fixed spray nozzle. For passage through the spray hood, one pot of each species (pre-emergence phase) is placed on the forward half of a wooden flat and one pot of established plants (post-mmergence phase) is placed on the rear half of the flat. Treatments are moved to the greenhouse after spraying. Watering during the observation period is applied only by sub-irrigation.
Compounds are screened initially at a rate of applica-tion equivalent to four to eight pounds per acre. Two weeks after treatment the pre- and post-emergence per cent injury is vi~ually rated. Subsequent testing was carried out at 2,1 and 0.5 pounds per acre.
1~4;~SS
Herbicidal testing of the compound of Example 1 showed the results set forth in Table I. The plants are tabulated using the following abbreviations:
Crabgrass CG
Johnson grass JG
Barnyard grass BG
Bean BN
Pigweed PW
Turnip TP
Cotton CT
Corn CN
.
. ~ , lQ4;~355 ~1 ~ ~ '`
CO er ~
E-.l o o o o o o o o o~
a o '71 H
~ O gl ~ ~ ~
~ OD ~ r~
~ i C~ ~
is an alkylamino group containing 4 to 6 carbon atoms, or a dialkylamino group in which the alkyl groups contain 4 to 6 carbon atoms, have herbicidal activity~ When n is 2 or more, more than one halogen species may be substituted in the ben-zene ring of the phenoxy group, that is the X's need not all be the same and, for example, both fluoro and chloro sub-stituents may be present in the same compound; reference to X
being halogen is to be understood in this sense.
The compounds of the above formula are novel and constitute one aspect of the present invention.
The present invention also comprises a herbicidal 16~43;~SS
composition comprising a compound according to the invention and a carrier therefor.
The compounds of this invention are readily prepared by the Ullmann ether synthesis reaction between an alkali metal (e.g., Na or K) salt of~a halophenol and a 5-halo (e.g., Cl or Br) -2-nitrobenzamide. The latter can readily be pre-pared from the corresponding 5-halo-2-nitrobenzoic acid which in turn can be readily prepared by nitrating an m-halotoluene, followed by oxidation of the methyl group by well known procedures. Alternatively~ and in most cases preferably, the Ullmann ether synthesis is carried out using the corresponding benzoic acid or benzoic acid ester, such as the methyl ester, and in the latter case the ether formed is hydrolyzed to obtain the benzoic acid. The product obtained in either case, that is the halophenoxy-nitro-benzoic acid, is then converted into the desired benzamide by any convenient procedure, preferably by converting the benzoic acid to the corresponding benzoyl chloride and reacting the latter with the appropriate alkylamine or dialkylamine to obtain the desired benzamide.
Compounds according to the invention include, for example:
N-sec-butyl-2-nitro-5-(2',4'-dichloro-6'-fluoro-phenoxy)-benzamide, N,N-di-sec-butyl-2-nitro-5-(2',4'-dichloro-6'-fluorophenoxy)-benzamide, N-hexyl-2-nitro-5-(2',4'-dichloro-6'-fluorophenoxy)-benzamide, and ~-sec-butyl-2-nitro-5-(2',4',6'-trichlorophenoxy)-benzamide.
~)43355 In order that the invention may be more fully understood, the following preparative examples are given by way of illustration only:
Example 1 Methyl-2-nitro-5-(2',4'-dichloro-6'-fluorophenoxy)-benzoate is hydrolyzed to the acid by heating a 10 percent solution of the methyl ester with a 5 percent solution of sodium hydroxide at 70C for 8 to 10 hours until a clear solution is obtained. The excess alkali is neutralized with HCl and the free benzoic acid filtered off.
The acid is then dissolved in benzene and refluxed for 5 to 7 hours with 20 percent excess thionyl chloride.
me solvent and thionyl chloride are stripped off after reaction i8 complete.
The benzoyl chloride is then dissolved in benzene and sec-butylamine added. Reaction takes place immediately with evolution of HCl. The mixture is refluxed for 2 hours to completion. The solvent is then stripped off to give the product, N-sec-butyl-2-nitro-5-(2',4'-dichloro-6'-fluoro-phenoxy)-benzamide which is then recrystallized from a mix-ture of ether and petroleum ether.
Example 2 Example 1 is repeated, but using di-sec-butylamine instead of sec-butylamine, to give N,N-di-sec-butyl-2-nitro--5-(2',4'-dichloro-6'-fluorophenoxy)-benzamide.
Example 3 Bxample 1 is repeated, but using hexylamine as the amine, to give N-hexyl-2-nitro-5-(2',4'-dichloro-6'-fluoro-phenoxy)-benzamide.
~ . ,, ~ .
Example 4 Example 1 is repeated, but starting with methyl-2--nitro-5-(2',4',6'-trichlorophenoxy)-benzoate, to give N-sec--butyl-2-nitro-5-(2',4',6'-trichlorophenoxy)-benzamide.
-.
_ 4 -.;
The compounds of this invention can be applied in various ways to achieve herbicidal action. They can be applied, per se, as solids or in vaporized form, but are preferably applied as the toxic components in pesticidal compositions of the compound and a carrier. The compositions can be applied, as dusts;
as liquid sprays, or as gas-propelled sprays and can contain, in addition to a carrier, additives such as emulsifying agents, binding agents, gases compressed to the liquid state, odorants, stabilizers, and the like. A wide variety of liquid and solid carriers can be used. Non-limiting examples of solid carriers include talc, bentonite, diatomaceous earth, pyrophyllite, fullers earth, gypsum, flours derived from cotton seeds and nut shells, and various natural and synthetic clays having a pH not exceed-ing about 9.5. Non-limiting examples of liquid carriers, include water; organic solvents, such as alcohols, ketones, amides and esters; mineral oils, such as kerosene, light oils, and medium oils and vegetable oils, such as cottonseed oil.
In practice, herbicidal application is measured in terms of pounds of herbicide applied per acre. The compounds of this invention are effective herbicides when applied in herbicidal amounts, i.e., at rates between about 0.2 pounds and about 10 pounds per acre.
HERBICIDAL EFFECTIVENESS
Method of Propagating Test Species Crabgress Digitaria Sanguinalis Yellow Foxtail Grass Setaria glauca Johnson grass Sorgum Halepense Barnyard grass Echinochloa crus-galli Amaranth pigweed Amaranthus retroflexus Turnip Brassica sp.
Cotton Gossypium hirsutum var. DPL
oth leaf Corn Zea Mays var. Golden Bantam Bean Phaseolus vulgaris var.
Black Valentine All crop and weed species are planted individually in 3" plastic pots containing potting soil. Four seeds of each of corn, cotton, and snapbeans are seeded to a depth equal to the diameter of the seed. All other species are surface seeded and sprinkled with screened soil in an amount sufficient to cover the seeds. Immediately after planting, all pots are watered by sub-irrigation in greenhouse trays. Pots for the pre-emergence phase are seeded one day before treatment.
1~43355 Planting dates for the post-emergence phase are varied so that all the seedlings will reach the desired stage of development simultaneously. The proper stage of seedling development for treatment in the post-emergence phase is as follows:
GRASSES: 2 inches in height PIGWEED & TURNIPS: 1 or 2 true leaves visible above cotyledons.
COTTON: first true leaf 1 inch in length; expanded cotyledons.
CORN: 3 inches - 4 inches in height BEANS: primary leaves expanded, grow-ing point at primary leaf node.
Method of Treatment Spray applications are made in a hood containing a movable belt and fixed spray nozzle. For passage through the spray hood, one pot of each species (pre-emergence phase) is placed on the forward half of a wooden flat and one pot of established plants (post-mmergence phase) is placed on the rear half of the flat. Treatments are moved to the greenhouse after spraying. Watering during the observation period is applied only by sub-irrigation.
Compounds are screened initially at a rate of applica-tion equivalent to four to eight pounds per acre. Two weeks after treatment the pre- and post-emergence per cent injury is vi~ually rated. Subsequent testing was carried out at 2,1 and 0.5 pounds per acre.
1~4;~SS
Herbicidal testing of the compound of Example 1 showed the results set forth in Table I. The plants are tabulated using the following abbreviations:
Crabgrass CG
Johnson grass JG
Barnyard grass BG
Bean BN
Pigweed PW
Turnip TP
Cotton CT
Corn CN
.
. ~ , lQ4;~355 ~1 ~ ~ '`
CO er ~
E-.l o o o o o o o o o~
a o '71 H
~ O gl ~ ~ ~
~ OD ~ r~
~ i C~ ~
Claims (10)
1. A halophenoxy-benzamide of the formula:
in which X is halogen, n is an integer of from 1 to 5, and R is an alkylamino group containing 4 to 6 carbon atoms or a dialkylamino group in which the alkyl groups contain from 4 to 6 carbon atoms.
in which X is halogen, n is an integer of from 1 to 5, and R is an alkylamino group containing 4 to 6 carbon atoms or a dialkylamino group in which the alkyl groups contain from 4 to 6 carbon atoms.
2. A compound according to claim 1 wherein said compound is N-sec-butyl 2-nitro-5-(2',4'-dichloro-6'-fluoro-phenoxy)benzamide.
3. A compound according to claim 1 wherein said compound is N,N-di(sec-butyl)-2-nitro-5-(2',4'-dichloro-6'--fluorophenoxy)benzamide.
4. A compound according to claim 1 wherein said compound is N-hexyl-2-nitro-5-(2',4'-dichloro-6'-fluoro-phenoxy)benzamide.
5. A compound according to claim 1 wherein said compound is N-sec-butyl-2-nitro-5-(2',4',6'-trichlorophenoxy)-benzamide.
6. A method of controlling plant growth, which comprises applying a herbicidally effective amount of a compound as defined in claim 1 to the plants or to the medium in which they are growing.
7. A method of controlling plant growth, which comprises applying a herbicidally effective amount of a compound as defined in claim 2 to the plants or to the medium in which they are growing.
8. A method of controlling plant growth, which comprises applying a herbicidally effective amount of a compound as defined in claim 3 to the plants or to the medium in which they are growing.
9. A method of controlling plant growth, which comprises applying a herbicidally effective amount of a compound as defined in claim 4 to the plants or to the medium in which they are growing.
10. A method of controlling plant growth, which comprises applying a herbicidally effective amount of a compound as defined in claim 5 to the plants or to the medium in which they are growing.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00334528A US3839444A (en) | 1971-11-01 | 1973-02-22 | Halophenoxy benzamide herbicides |
| US396976A US3873303A (en) | 1971-11-01 | 1973-09-12 | Herbicidal use and compositions of halophenoxy benzamides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1043355A true CA1043355A (en) | 1978-11-28 |
Family
ID=26989254
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA191,956A Expired CA1043355A (en) | 1973-02-22 | 1974-02-07 | Halophenoxy benzamide herbicides |
Country Status (7)
| Country | Link |
|---|---|
| JP (2) | JPS49116230A (en) |
| CA (1) | CA1043355A (en) |
| DE (1) | DE2408433A1 (en) |
| FR (1) | FR2218832B2 (en) |
| GB (1) | GB1432752A (en) |
| IT (1) | IT1049529B (en) |
| NL (1) | NL7402490A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4173464A (en) * | 1976-05-07 | 1979-11-06 | Sumitomo Chemical Company, Limited | m-Phenoxybenzamide derivatives |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4843609A (en) * | 1971-10-05 | 1973-06-23 |
-
1974
- 1974-01-25 JP JP1029374A patent/JPS49116230A/ja active Pending
- 1974-02-07 CA CA191,956A patent/CA1043355A/en not_active Expired
- 1974-02-12 GB GB639774A patent/GB1432752A/en not_active Expired
- 1974-02-21 FR FR7405994A patent/FR2218832B2/fr not_active Expired
- 1974-02-21 DE DE19742408433 patent/DE2408433A1/en not_active Ceased
- 1974-02-22 NL NL7402490A patent/NL7402490A/xx not_active Application Discontinuation
- 1974-04-08 IT IT2087874A patent/IT1049529B/en active
-
1978
- 1978-07-28 JP JP9162578A patent/JPS5444023A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5444023A (en) | 1979-04-07 |
| DE2408433A1 (en) | 1974-09-19 |
| JPS5510563B2 (en) | 1980-03-17 |
| FR2218832B2 (en) | 1977-06-10 |
| NL7402490A (en) | 1974-08-26 |
| FR2218832A2 (en) | 1974-09-20 |
| IT1049529B (en) | 1981-02-10 |
| JPS49116230A (en) | 1974-11-06 |
| GB1432752A (en) | 1976-04-22 |
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