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US3624151A - Glyoxylanilideoximino carbamates - Google Patents

Glyoxylanilideoximino carbamates Download PDF

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US3624151A
US3624151A US675306A US3624151DA US3624151A US 3624151 A US3624151 A US 3624151A US 675306 A US675306 A US 675306A US 3624151D A US3624151D A US 3624151DA US 3624151 A US3624151 A US 3624151A
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compound according
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methyl
lower alkyl
hydrogen
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US675306A
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Arnold D Gutman
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Stauffer Chemical Co
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Stauffer Chemical Co
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/60—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups having oxygen atoms of carbamate groups bound to nitrogen atoms
    • 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
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Definitions

  • R, and R are, independently hydrogen, lower alkyl
  • allyl, and cycloalkyl having from three to six carbon atoms, in-
  • X is halogen or lower alkyl having one to four carbon 1 atoms, inclusive; and n is an integer having a value from 0 to 4,
  • GLYOXYLANILIDEOXIMINO CARBAMATES This invention relates to novel compounds useful as active herbicidal substances. More specifically, this invention relates to a novel type of glyoxylanilideoximino carbamates and their use as effective herbicides.
  • novel compounds of the present invention correspond to the formula:
  • desirable vegetation comprises applying an herbicidally effective amount of the above represented compounds to the area where control is desired.
  • lower alkyl preferably includes those members of the group which contain from one to about six carbon atoms, inclusive, in both straight chain and branched chain configurations.
  • halogen preferably includes fluorine, chlorine and bromine.
  • X preferably includes mono-, di-, tri-, and tetrasubstitution on the phenyl ring. For example, monochlorophenyl, dichlorophenyl, trichlorophenyl and tetrachlorophenyl, similarly dichlorodimethylphenyl, trifluoromonomethylphenyl and the like.
  • novel class of compounds of this invention are prepared by one of several general methods.
  • One such general method is the condensation between an appropriate is'ocyanate or carbamoyl chloride and an appropriate glyoxylanilide oxime. The reaction proceeds readily in the liquid phase.
  • the employment of a solvent also is useful in facilitating processing, as well as aiding during the agitation and mixing of the reactants.
  • catalyst 7 may be employed to enhance the reaction. No catalyst is required.
  • catalysts as di-n-butyltin dilaurate or triethylamine are efiective catalysts.
  • the reactions preferably are carried out at temperatures that permit operation in the liquid phase. These temperatures are between about room temperature and reflux temperature of the solvent, if one is employed.
  • Glyoxylanilide oxime 6.0 g. (0.036 m.) ispartially dissolved in 25 ml. of acetone. A slight excess of methyl isoeyanate is added along with three drops of dibutyltin dilaurate. After approximately a 10 minute reaction induction period the temperature autogeneously increased from room temperature to C. During this period the solution becomes clear. The product crystallizes out of solution at room temperature. A second crop of crystals is collected by adding hexane. There is obtained 7.0 g. of the title compound, m.p. at 62 C. with decomposition. The identity of the product was confirmed by elemental analysis: Calculated: Carbon, 54.3 percent, H, 4.95 percent. Found: Carbon, 54.13 percent, H, 4.84 percent.
  • difierent weed species are planted in individual rows using one species per row across the width of the flat.
  • the seeds used are hairy crabgrass (Digitaria sanguinatis (L.) Scop.), yellow foxtail,
  • Seeds of five weed species including hairy crabgrass, watergrass, wild oats, lndian mustard, and curly dock and one crop pinto beans are planted in flats as described above for preemergence screening.
  • the flats are placed in the greenhouse at 7285 F. and watered daily with a sprinkler.
  • the spray is prepared by weighing out 50 mg. of the test compound, dissolving it in ml. of acetone containing 1 percent Tween (polyoxy-ethylene sorbitan monolaurate) and then adding 5 ml. of water.
  • the solution is sprayed on the foliage using an atomizer.
  • the spray concentration is 0.5 percent and the rate would be approximately 20 lb./acre if all of v the spray were retained on the plant and soil, but some spray is lost so it is estimated that the application rate is approximately 12.5 lb./acre.
  • Beans are used to detect defoliants and plant growth regulators.
  • the beans are trimmed to two or three plants per flat by cutting off the excess weaker plants several days before treatment.
  • the treated plants are placed back in the greenhouse and care is taken to avoid sprinkling the treated foliage with water for three days after treatment. Water is applied to the soil by means of a slow stream from a watering hose taking care not to wet the foliage.
  • the new compounds of the present invention are used as preemergence or post-emergence herbicides and are applied in a variety of ways at various concentrations.
  • the compounds are formulated with an inert carrier, utilizing methods well known to those skilled in the art, thereby making them suitable for application as dusts, sprays, or drenches and the like, in the form and manner required.
  • the mixtures can be dispersed in water with the aid of a wetting agent or they can be employed in organic liquid compositions, oil and water, water in oil emulsions, with or without the addition of wetting, 2 dispersing or emulsifying agents.
  • the amount applied depends upon the nature of the seeds or plants to be controlled and the rate of application varies from 1 to approximately 50 pounds per acre.
  • One particularly advantageous way of applying the compound is a narrow band along a row crop straddling the row.
  • the compounds are formulated with an inert carrier utilizing methods well known to those skilled in the art, thereby making them suitable for particular application.
  • R is allyl and n is 0.
  • R is lower alkyl
  • X is halogen
  • n is l to 4, inclusive.
  • R is allyl
  • X is halogen
  • n is l to 4, inclusive.
  • R is hydrogen
  • R is lower alkyl
  • X is lower alkyl having one to four carbon atoms inclusive
  • n is l to 4, inclusive.
  • R is A compound Coming claim 17 in which is hydrogen, R is cycloalkyl having from three to six carbon methyhxis chlorine and methyhandnis atoms inclusive,andnis 0. w-

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

New compounds corresponding to the formula:

IN WHICH R1 and R2 are, independently, hydrogen, lower alkyl, allyl, and cycloalkyl having from three to six carbon atoms, inclusive; X is halogen or lower alkyl having one to four carbon atoms, inclusive; and n is an integer having a value from 0 to 4, inclusive. The above compounds are effective herbicides, particularly for the control of grasses and broadleaf plants, with both preemergence and post-emergence activity. Representative compounds are: glyoxylanilideoximino-N''-allyl carbamate, glyoxylanilideoximino-N''-n-butyl carbamate, glyoxyl3,4-dichloroanilideoximino-N''-methyl carbamate, and glyoxylanilideoximino-N''-n-propyl carbamate.

Description

United States Patent [72] lnventor Arnold D. Gutman Pincle, Calil. [2|] Appl. No. 675,306 [22] Filed Oct. 16, 1967 [45] Patented Nov. 30, 971 [73] Assignee Staulfer Chemical Company New York, N.Y.
[54] GLYOXYLANILIDEOXIMINO CARBAMATES 18 Claims, No Drawings [52] U.S. Cl 260/557 R, 560/562 N, 71/118 [5 l Int. Cl C07c 103/33 [50] Field 0! Search 260/562 X, 562, 557
[56] References Cited UNITED STATES PATENTS 3,420,817 1/1969 Stemple et al. 260/562 1 Primary Examiner-Henry R. .liles Assistant Examiner--Harry l. Moatz Attorneys-Wayne C. Jaeschke and Edwin H. Baker ABSTRACT: New compounds corresponding to the formula:
in which R, and R, are, independently hydrogen, lower alkyl,
' allyl, and cycloalkyl having from three to six carbon atoms, in-
elusive; X is halogen or lower alkyl having one to four carbon 1 atoms, inclusive; and n is an integer having a value from 0 to 4,
ylanilideoximino-N'-n-propylcarbamate.
GLYOXYLANILIDEOXIMINO CARBAMATES This invention relates to novel compounds useful as active herbicidal substances. More specifically, this invention relates to a novel type of glyoxylanilideoximino carbamates and their use as effective herbicides.
The novel compounds of the present invention correspond to the formula:
desirable vegetation comprises applying an herbicidally effective amount of the above represented compounds to the area where control is desired. I
The term lower alkyl, unless otherwise defined, preferably includes those members of the group which contain from one to about six carbon atoms, inclusive, in both straight chain and branched chain configurations. The term halogen preferably includes fluorine, chlorine and bromine. X preferably includes mono-, di-, tri-, and tetrasubstitution on the phenyl ring. For example, monochlorophenyl, dichlorophenyl, trichlorophenyl and tetrachlorophenyl, similarly dichlorodimethylphenyl, trifluoromonomethylphenyl and the like.
The following table is exemplary of compounds of this invention.
The novel class of compounds of this invention are prepared by one of several general methods. One such general method is the condensation between an appropriate is'ocyanate or carbamoyl chloride and an appropriate glyoxylanilide oxime. The reaction proceeds readily in the liquid phase. The employment of a solvent also is useful in facilitating processing, as well as aiding during the agitation and mixing of the reactants. A
7 catalyst may be employed to enhance the reaction. No catalyst is required. Such catalysts as di-n-butyltin dilaurate or triethylamine are efiective catalysts. The reactions preferably are carried out at temperatures that permit operation in the liquid phase. These temperatures are between about room temperature and reflux temperature of the solvent, if one is employed.
The following examples are presented to show how certain specific compounds of the invention are prepared and to illustrate the effectiveness ofcertain compounds of the invention as herbicides.
EXAMPLE I Preparation of glyoxylanilideoximino-N' methyl carbamate.
Glyoxylanilide oxime, 6.0 g. (0.036 m.) ispartially dissolved in 25 ml. of acetone. A slight excess of methyl isoeyanate is added along with three drops of dibutyltin dilaurate. After approximately a 10 minute reaction induction period the temperature autogeneously increased from room temperature to C. During this period the solution becomes clear. The product crystallizes out of solution at room temperature. A second crop of crystals is collected by adding hexane. There is obtained 7.0 g. of the title compound, m.p. at 62 C. with decomposition. The identity of the product was confirmed by elemental analysis: Calculated: Carbon, 54.3 percent, H, 4.95 percent. Found: Carbon, 54.13 percent, H, 4.84 percent.
TABLE I 35 The following table, table ll, is a listing of compounds which X H 0 0 R are similarly prepared in accordance with the above given exl 11 ample. Compound numbers have been assigned to them and NTCCH=NOON\ are used for identification throughout the balance of the p i seti TABLE II Xu H O 0 R1 I I! ll NCGH=NOCN Compound Number Kn R1 R1 M.P. C. or no" Hydrogen... Methyl 62 (decomposition). 2. do Ally] (Semi-solid). 3. .-..do.-.---- n-Buty1 Do. 4. 3-ehloro-4-methyl ..do...-... Methyl 1054i (decomposition). 5... 3,4-dichloro do..-. do. 101-3 (decomposition). 6 d A1lyL.. (Viscous o n-ButyL. 129-129.5 Methyl... 0-71". CyclohexyL. 176-178 ..do. i-Propyl. Oil-110 do. n-Propyl.... 1
L e ..W
x, HERBICIDAL SCREENING TESTS Hydrogen Methyl.
o Allyl- As previously mentioned, the herein described new commend-{teeter .1138:11113311131": fileiii' positions produced in the above described manner are 3, 4410 loro suds.-. A 11)o. phytotoxic compounds wh ch are useful and valuable In con- 4-fiuoro... Methyl... Methyl. 3, 4-dleh1oro. (Jyclobutyl Allyl. Cyclopropyl Methyl.
trolling various plant species. Compounds of this invention are tested as herbicides in the following manner. Preemergence herbicide test:
On the day preceding treatment, seeds of seven difierent weed species are planted in individual rows using one species per row across the width of the flat. The seeds used are hairy crabgrass (Digitaria sanguinatis (L.) Scop.), yellow foxtail,
(Setaria Glauca (L.) Beauv.), watergrass (Echinochloa e Ample seeds are planted to give about 20 to 50 seedlings per row, depending on the size of the plants. The flats are watered several untreated control flats. The rating system is as follows:
-= no significant injury (-15 percent control) slight injury (25-35 percent control) -H= moderate injury (55-65 percent control) -l++-= severe injury or death (85- 00 percent control) An activity index is used to represent the total activity on all seven weed species. It is the sum of the number of plus marks, so that an activity index of 21 represents complete control of all seven weeds. The results of this test are reported in table 11. Postemergence Herbicide Test:
Seeds of five weed species including hairy crabgrass, watergrass, wild oats, lndian mustard, and curly dock and one crop pinto beans (Phaseolus vulgaris), are planted in flats as described above for preemergence screening. The flats are placed in the greenhouse at 7285 F. and watered daily with a sprinkler. About l0 to 14 days after planting when the primary leaves of the bean plant are almost fully expanded and the first trifoliate leaves are just starting to form, the plants are sprayed. The spray is prepared by weighing out 50 mg. of the test compound, dissolving it in ml. of acetone containing 1 percent Tween (polyoxy-ethylene sorbitan monolaurate) and then adding 5 ml. of water. The solution is sprayed on the foliage using an atomizer. The spray concentration is 0.5 percent and the rate would be approximately 20 lb./acre if all of v the spray were retained on the plant and soil, but some spray is lost so it is estimated that the application rate is approximately 12.5 lb./acre.
Beans are used to detect defoliants and plant growth regulators. The beans are trimmed to two or three plants per flat by cutting off the excess weaker plants several days before treatment. The treated plants are placed back in the greenhouse and care is taken to avoid sprinkling the treated foliage with water for three days after treatment. Water is applied to the soil by means of a slow stream from a watering hose taking care not to wet the foliage.
Injury rates are recorded 14 days after treatment. The rating system is the same as described above for thepreemergence test where (-H-) and (-l-ll-)are used for the different rates of injury and control. The injury symptoms are also recorded. The maximum activity index for complete control of all the species in the post-emergence screening test is 18 which represents the sum of the plus marks obtained with the six plant species used in the test. The herbicide activity indices are shown in table 111.
The new compounds of the present invention are used as preemergence or post-emergence herbicides and are applied in a variety of ways at various concentrations. In practice the compounds are formulated with an inert carrier, utilizing methods well known to those skilled in the art, thereby making them suitable for application as dusts, sprays, or drenches and the like, in the form and manner required. The mixtures can be dispersed in water with the aid of a wetting agent or they can be employed in organic liquid compositions, oil and water, water in oil emulsions, with or without the addition of wetting, 2 dispersing or emulsifying agents. The amount applied depends upon the nature of the seeds or plants to be controlled and the rate of application varies from 1 to approximately 50 pounds per acre. One particularly advantageous way of applying the compound is a narrow band along a row crop straddling the row. In practice the compounds are formulated with an inert carrier utilizing methods well known to those skilled in the art, thereby making them suitable for particular application.
The concentration of a compound of the present invention, constituting an effective amount in best mode of administration in the utility disclosed is readily determinable by those skilled in the art. Various changes and modifications are possible without departing from the spirit and scope of the invention described herein and will be apparent to those skilled in the art to which it pertains. It is accordingly intended that the present invention shall only be limited by the scope of the claims.
What is claimed is:
l. A compound corresponding to the formula Xn Iii: (If R1 in which R and R are independently selected from the group consisting of hydrogen, lower alkyl, ally] and cycloalkyl having from threetto six carbon atoms, inclusive; X is selected from the group consisting of fluorine, chlorine, bromine and lower alkyl having from one to four carbon atoms, inclusive; and n is an integer having a value from zero to four, inclusive.
2. A compound according to claim 1 in which R, is hydrogen, R, is lower alkyl and n is O.
3. A compound according to claim 2 in which R, is methyl.
4. A compound according to claim 2 in which R, is n-butyl.
5. A compound according to claim 2 in which R, is i-propyl.
6. A compound according to claim 2 in which R, is npropyl.
7. A compound, according to claim 1 in which R, is
1 hydrogen, R, is allyl and n is 0.
8. A compound according to claim 1 in which R, is
hydrogen, R, is lower alkyl, X is halogen and n is l to 4, inclusive.
9. A compound according to claim 8 in which R, is methyl, X is chlorine andn is 2.
10. A compound according to claim 1 in which R, is
hydrogen, R, is allyl, X is halogen and n is l to 4, inclusive.
11. A compound according to claim 10 in which X is chlorine and n is 2.
12. A compound according to claim 1 in which R, is hydrogen, R, is lower alkyl, X is lower alkyl having one to four carbon atoms inclusive, and n is l to 4, inclusive.
13. A compound according to claim 12 in which R is 16. A compound according to claim 15 in which R is methyl, X is methyl and n is 2. cyclohexyl.
, 17, A compound according to claim 1 in which R is hydrogen, R is lower alkyl, X is halogen and lower alkyl andn is 2 to 4 inclusive.
[5. A compound according to claim 1 in which R is A compound Coming claim 17 in which is hydrogen, R is cycloalkyl having from three to six carbon methyhxis chlorine and methyhandnis atoms inclusive,andnis 0. w-
14. A compound according to claim 12 in which R is n-butyl, X is methyl and n is 2.

Claims (17)

  1. 2. A compound according to claim 1 in which R1 is hydrogen, R2 is lower alkyl and n is 0.
  2. 3. A compound according to claim 2 in which R2 is methyl.
  3. 4. A compound according to claim 2 in which R2 is n-butyl.
  4. 5. A compound according to claim 2 in which R2 is i-propyl.
  5. 6. A compound according to claim 2 in which R2 is n-propyl.
  6. 7. A compound, according to claim 1 in which R1 is hydrogen, R2 is allyl and n is 0.
  7. 8. A compound according to claim 1 in which R1 is hydrogen, R2 is lower alkyl, X is halogen and n is 1 to 4, inclusive.
  8. 9. A compound according to claim 8 in which R2 is methyl, X is chlorine andn is 2.
  9. 10. A compound according to claim 1 in which R1 is hydrogen, R2 is allyl, X is halogen and n is 1 to 4, inclusive.
  10. 11. A compound according to claim 10 in which X is chlorine and n is 2.
  11. 12. A compound according to claim 1 in which R1 is hydrogen, R2 is lower alkyl, X is lower alkyl having one to four carbon atoms inclusive, and n is 1 to 4, inclusive.
  12. 13. A compound according to claim 12 in which R2 is methyl, X is methyl and n is 2.
  13. 14. A compound according to claim 12 in which R2 is n-butyl, X is methyl and n is 2.
  14. 15. A compound according to claim 1 in which R1 is hydrogen, R2 is cycloalkyl having from three to six carbon atoms inclusive, and n is 0.
  15. 16. A compound according to claim 15 in which R2 is cyclohexyl.
  16. 17. A compound according to claim 1 in which R1 is hydrogen, R2 is lower alkyl, X is halogen and lower alkyl and n is 2 to 4 inclusive.
  17. 18. A compound according to claim 17 in which R2 is methyl, X is chlorine and methyl, and n is 2.
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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2504319A1 (en) * 1974-02-05 1975-08-07 Shell Int Research N, N-DISUBSTITUTED ALANINE DERIVATIVES, METHOD FOR THEIR PRODUCTION AND USE AS HERBICIDES
US4041072A (en) * 1975-03-25 1977-08-09 Delalande S. A. Acetamidoxime compounds
US4260410A (en) * 1978-03-31 1981-04-07 Chevron Research Company Herbicidal and plant-growth-regulating N-haloacetylphenylamino carbonyl oximes
EP2118052A2 (en) * 2007-03-15 2009-11-18 Sun Pharma Advanced Research Company Ltd Novel prodrugs

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3420817A (en) * 1966-12-06 1969-01-07 Hoffmann La Roche 4,1,5-benzoxadiazocin-2-ons and processes for preparing same

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3420817A (en) * 1966-12-06 1969-01-07 Hoffmann La Roche 4,1,5-benzoxadiazocin-2-ons and processes for preparing same

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2504319A1 (en) * 1974-02-05 1975-08-07 Shell Int Research N, N-DISUBSTITUTED ALANINE DERIVATIVES, METHOD FOR THEIR PRODUCTION AND USE AS HERBICIDES
US4041072A (en) * 1975-03-25 1977-08-09 Delalande S. A. Acetamidoxime compounds
US4260410A (en) * 1978-03-31 1981-04-07 Chevron Research Company Herbicidal and plant-growth-regulating N-haloacetylphenylamino carbonyl oximes
EP2118052A2 (en) * 2007-03-15 2009-11-18 Sun Pharma Advanced Research Company Ltd Novel prodrugs
EP2118052A4 (en) * 2007-03-15 2010-04-14 Sun Pharma Advanced Res Co Ltd Novel prodrugs

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