US3063823A - Method of killing weeds and influencing plant growth - Google Patents

Method of killing weeds and influencing plant growth Download PDF

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Publication number
US3063823A
US3063823A US709169A US70916958A US3063823A US 3063823 A US3063823 A US 3063823A US 709169 A US709169 A US 709169A US 70916958 A US70916958 A US 70916958A US 3063823 A US3063823 A US 3063823A
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US
United States
Prior art keywords
plant growth
plants
weeds
mustard
oat
Prior art date
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Expired - Lifetime
Application number
US709169A
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English (en)
Inventor
Kuhle Engelbert
Schafer Werner
Eue Ludwig
Wegler Richard
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Bayer AG
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Bayer AG
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Publication date
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Publication of US3063823A publication Critical patent/US3063823A/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/53—Nitrogen atoms

Definitions

  • the present invention relates to and has as its objects agents for killing weeds and influencing plant growth and a method of employing same.
  • the inventive compositions contain as essential active ingredients carbamide oximes of the following general formula
  • R R and R stand for the following groups: hydrogen, low molecular weight alkyl groups of maximum 8 carbon atoms (R R and R may also be different), R and R may also be linked to one another, as for example in the cyclohexane or cycloheptane radical, they may also be unsaturated alkyl groups, alkyl groups being substituted by hetero atoms such as halogen or nitrogen, alkyl groups broken up by hetero atoms such as ether groups, alkyl radicals with or without substituents (halogen, nitro, alkyl, hydroxy or alkoxy groups being chiefly the substituents), heterocyclic radicals such as the'pyridine or furan radical.
  • R may also be an aryl radical.
  • R may also be an aryl or alkyl radical
  • the herbicidal composition of the present invention may be prepared by usual methods, i.e. preferably by mixing the active ingredient with solid or liquid carriers or conditioning agents as they are used as pest control adjuvant or modifiers for formulations adapted for the application to soil, weeds or unwanted plants using ap plicator equipments.
  • Solid compositions are preferably in the form of dusts and are compounded to give homogeneous free-flowing dusts by admixing the active compound with finely divided solids preferably talcs, natural clays, pyrophyllite, diatomaceous earth, and flours such as walnut shell, wheat, redwood, soya bean, cottonseed flours, and other inert solid carriers of the kind conventionally employed in preparing pest control compositions and dusts or powdered form.
  • finely divided solids preferably talcs, natural clays, pyrophyllite, diatomaceous earth, and flours such as walnut shell, wheat, redwood, soya bean, cottonseed flours, and other inert solid carriers of the kind conventionally employed in preparing pest control compositions and dusts or powdered form.
  • Liquid compositions employing the active ingredients are prepared in the usual way by admixing the active ingredient with a conventional liquid diluent media.
  • the active ingredients are quite insoluble in most liquids although solutions containing them at low concentration can be made if desired using various of the common organic solvents such as cyclohexanol, acetone, ethanol, isobutanol, furfural, isopropyl acetate, and the like.
  • the liquid compositions are prepared in more concentrated form so that the liquid composition is primarily a suspension of the active compound in the liquid.
  • herbicidal compositions of the invention whether in the form of dusts or liquids preferably also include a surface active dispersing agent of the kind sometimes referred to in the art as wetting, dispersing, and emulsifying agents.
  • the surface active dispersing agents employed can be of the anionic, cationic, or nonionic type and include for example, sodium oleate, sulfonated petroleum oils, sodium lauryl sulfate, polyethylene oxides, and other surface active dispersing agents such as those listed in detail in articles by McCutcheon in Soap and Sanitary Chemicals, August, September, and October of 1949.
  • compositions of the invention will vary depending upon the effectiveness of the particular surface active dispersing agent employed and the properties of other materials in the composition. Generally, the surface active dispersing agent will not comprise more than about 30% by weight of the composition and with the better materials will be 5% or less.
  • the content of the active ingredient employed in the herbicidal compositions of the invention will vary according to the manner in which and the purpose for which the composition is to be applied but in general will be from 0.5 to by Weight of the composition.
  • the herbicidal compositions are applied either as a spray or in the form of a dust to the locus or area to be protected from undesirable plant growth.
  • the active ingredient is, of course, applied in amount sufiicient to exert the desired plant killing action.
  • the application can be made directly upon the locus or area during the period of infestation of unwanted plant growth or alternatively the application can be made in advance of an anticipated infestation.
  • the compositions of the invention are preferably applied after planting of the crop seeds but before emergence of the seedlings.
  • the applications are of the pre-emergence type.
  • Fertilizer materials other herbicidal agents, and other pest control agents such as insecticides and fungicides can be includedin the herbicidal compositions of the invention if desired.
  • the above mentioned compounds act particularly on dicotyledonous plants such as cress, mustard and charlock, their action is selective, and therefore the combating of weeds can be effected in corn or green land with protection of the cultivated plants. With increased concentration also monocotyledonous plants can be destroyed so that at an appropriate concentration the compounds are also suitable for total weed control.
  • aqueous emulsions of the inventive active ingredients since thereby distribution in the soil is most efllciently accomplished.
  • Such aqueous emulsions may be prepared as described above from either pure active ingredient-auxiliary solvent-emulsifier-pre-mixtures or from dusts containing additional emulsifiers.
  • weeds can take place at any stage weeds may consist of a mixture of various of the aforeu said compounds and a solid or liquid diluent, to which known herbicides or fertilizers may be added.
  • Emulsions have been prepared from N-phenyl-carbamide acetone oxime as shown in Example 1; such solutions containing 0.01% of activeingredient completely destroy mustard and charlock when used in an amount of 1000 Example 1 litres per hectare. At this concentration oat is not dam- 100 mg f N Pheny1 carbamide acetone Oxime are aged. With concentrations of 0.5% also oat is destroyed. mixed with 3 ml. of acetone. 2 drops of benzyl hydroxy Example 3 diphenyl polyglycol ether (containing about 15 glycol 0 1 1 residues) are added.
  • This premixture is further diluted 2 or emulsions of N' m' carbamldle with Water to a volume of 100 ml.
  • This aqueous solution acetone Qxlms are Prepared desqnbed P is applied to mustard and oats as follows: in the green p g en h p yed drtp wetwithhthis so u ⁇ -1 house young mustard plants (with 2 leaves) and oat of s S complete defohanon of t e Frenc about cm. high are sprayed with the solutions as pre- 15 can-S e5 p E 1 I 4 pared above.
  • o o 2 m 34, 0 0 H36 H3O CH3 /G N-0(fi-NH C ⁇ 3-4 m 3, 0 0 H30 0 CH;
  • nasturtium plant test have been carried out for determination of inhibiting plant growth as follows: nasturtium seeds are placed on filter paper in glasses of about 5 inches height and about 2 inches diameter in such way that the filter paper is partially placed in a solution containing the active ingredient of the concentration indicated above. Evaluation of growth of the nasturtium seeds occurred after 6 days.
  • the figures in the column under nasturtium plant test mean:
  • Tests on Phaseolus vulgaris and on mustard oat postemergence have been carried out by spraying young plants of about 5 to 6 inches height drip wet. Evaluation occurred after 20 days.
  • the evaluation numbers mean:
  • a method of killing weeds and inhibiting plant growth which comprises treating the plants with an effective amount of the compound of the formula 3.
  • a method of killing weeds and inhibiting plant growth which comprises treating the plants with an effective amount of the compound of the formula 4.
  • a method of kiling weeds and inhibiting plant growth which comprises treating the plants with an effective amount of the compound of the formula 5.
  • a method of killing weeds and inhibiting plant growth which comprises treating the plants with an efi'ective amount of the compound of the formula CEa CH3 OH: 0 CH 6.
  • a method of killnig weeds and inhibiting plant growth which comprises treating the plants with an effective amount of the compound of the formula 7.
  • a method of killing weeds and inhibiting plant growth which comprises treating the plants with an efiective amount of the compound of the formula 8.
  • a method of killing weeds and inhibiting plant growth which comprisestre-ating plants with an efiective amount of a compound of the following general formula:
  • R and R are each selected from the group consisting of hydrogen, lower alkyl radicals having up to 8 carbon atoms and a phenyl radical; and R is selected from the group consisting of lower alkyl radicals having up to 8 carbon atoms, lower chloroalkyl chloroacetoxyethyl, phenyl, lower alkyl-substituted phenyl, chlorophenyl, lower alkyl-substituted chlorophenyl and lower alkoxy phenyl,

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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)
US709169A 1957-01-21 1958-01-16 Method of killing weeds and influencing plant growth Expired - Lifetime US3063823A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF22179A DE1024746B (de) 1957-01-21 1957-01-21 Mittel zur Unkrautbekaempfung und Beeinflussung des Pflanzenwachstums

Publications (1)

Publication Number Publication Date
US3063823A true US3063823A (en) 1962-11-13

Family

ID=7090346

Family Applications (1)

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US709169A Expired - Lifetime US3063823A (en) 1957-01-21 1958-01-16 Method of killing weeds and influencing plant growth

Country Status (7)

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US (1) US3063823A (en(2012))
BE (1) BE564131A (en(2012))
CH (1) CH366690A (en(2012))
DE (1) DE1024746B (en(2012))
FR (1) FR1190302A (en(2012))
GB (1) GB824534A (en(2012))
NL (2) NL224194A (en(2012))

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3299137A (en) * 1962-09-25 1967-01-17 Union Carbide Corp Acyclic hydrocarbon aldehyde carbamoyl oximes
US3400153A (en) * 1964-09-23 1968-09-03 Union Carbide Corp Nitroalkyl carbamoyloximes
US3454642A (en) * 1966-12-22 1969-07-08 Upjohn Co Alkyl 2-methylpropenyl ketoxime carbamates
US3483246A (en) * 1966-12-05 1969-12-09 Mobil Oil Corp Aromatic glyoxynitrile oximino carbanates
US3495968A (en) * 1969-04-17 1970-02-17 Mobil Oil Corp Herbicidal composition and method of use
US3515536A (en) * 1968-07-15 1970-06-02 Fmc Corp Phenyl-glyoxime as a novel plant growth regulator
US3541150A (en) * 1968-05-15 1970-11-17 Stauffer Chemical Co Certain aldoxime substituted carbamates and their use as insecticides and acaricides
US3708590A (en) * 1970-07-02 1973-01-02 Stauffer Chemical Co Method of controlling acarids with certain oxime esters
US3726921A (en) * 1967-01-03 1973-04-10 Gen Mills Inc Novel derivatives of polyisocyanates prepared from polymeric fat acids and certain oximes
US3819358A (en) * 1971-02-23 1974-06-25 Chemagro Corp Retarding plant growth with cyclohexenone oximes
US3880926A (en) * 1968-07-17 1975-04-29 Velsicol Chemical Corp New compositions of matter
US3903303A (en) * 1970-07-06 1975-09-02 Stauffer Chemical Co Controlling fungi and bacteria with certain oxime esters
US3932509A (en) * 1970-03-23 1976-01-13 Ciba-Geigy Corporation Carbamoyloximes derivatives
US4030912A (en) * 1973-04-11 1977-06-21 Hercules Incorporated Certain oximinyl allophanates and their use as herbicides
US4115093A (en) * 1975-10-28 1978-09-19 Hercules Incorporated Certain oximinyl allophanates and their use as herbicides
EP0039308A1 (de) * 1980-04-24 1981-11-04 Ciba-Geigy Ag Cyclobutanonoximcarbamate, Verfahren zu ihrer Herstellung und ihre Verwendung in der Schädlingsbekämpfung sowie die als Zwischenprodukte dienenden Cyclobutanonoxime
US4336199A (en) * 1981-07-10 1982-06-22 Morton-Norwich Products, Inc. 5-(2,4-Dichlorophenyl)-3-furancarboxaldehyde-O-[(methylamino)carbonyl]oxime
US20130019525A2 (en) * 2010-10-05 2013-01-24 Nahum Shpak Plant growth medium
US10962652B2 (en) 2010-10-08 2021-03-30 Samsung Electronics Co., Ltd. Determining context of a mobile computer

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH399823A (de) * 1959-04-28 1965-09-30 Philips Nv Mittel zur Beeinflussung des Wachstums von Pflanzen
BE637723A (en(2012)) * 1962-09-25
NL302370A (en(2012)) * 1962-12-22
GB1063363A (en) * 1963-03-14 1967-03-30 African Explosives & Chem Improvements in or relating to insecticidal compounds of the phenyl or naphthyl carbamoyl oxime type
DE1221840B (de) * 1963-09-21 1966-07-28 Bayer Ag Mittel zur Bekaempfung von Wasserunkraeutern
US3547621A (en) * 1967-05-29 1970-12-15 Gulf Research Development Co Method of combating weeds
US3875232A (en) * 1971-04-08 1975-04-01 Diamond Shamrock Corp AC Ketoxime carbamates
JPS5531039A (en) 1978-08-25 1980-03-05 Sumitomo Chem Co Ltd Oximecarbamate derivative, its preparation, and microbicide and herbicide containing the same
AT365410B (de) * 1978-08-31 1982-01-11 Ciba Geigy Ag Mittel zum schutz von kulturpflanzen vor aggressi-ven herbiziden
US4347372A (en) * 1978-09-01 1982-08-31 Ciba-Geigy Corporation Benzoxazolyl-glyoxylonitrile-2-oxime ether derivatives

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2416198A (en) * 1943-04-08 1947-02-18 Staley Mfg Co A E Growth promoting substances
US2769702A (en) * 1952-02-09 1956-11-06 Frank J Sowa Herbicidal composition

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2416198A (en) * 1943-04-08 1947-02-18 Staley Mfg Co A E Growth promoting substances
US2769702A (en) * 1952-02-09 1956-11-06 Frank J Sowa Herbicidal composition

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3299137A (en) * 1962-09-25 1967-01-17 Union Carbide Corp Acyclic hydrocarbon aldehyde carbamoyl oximes
US3400153A (en) * 1964-09-23 1968-09-03 Union Carbide Corp Nitroalkyl carbamoyloximes
US3483246A (en) * 1966-12-05 1969-12-09 Mobil Oil Corp Aromatic glyoxynitrile oximino carbanates
US3454642A (en) * 1966-12-22 1969-07-08 Upjohn Co Alkyl 2-methylpropenyl ketoxime carbamates
US3726921A (en) * 1967-01-03 1973-04-10 Gen Mills Inc Novel derivatives of polyisocyanates prepared from polymeric fat acids and certain oximes
US3541150A (en) * 1968-05-15 1970-11-17 Stauffer Chemical Co Certain aldoxime substituted carbamates and their use as insecticides and acaricides
US3515536A (en) * 1968-07-15 1970-06-02 Fmc Corp Phenyl-glyoxime as a novel plant growth regulator
US3880926A (en) * 1968-07-17 1975-04-29 Velsicol Chemical Corp New compositions of matter
US3495968A (en) * 1969-04-17 1970-02-17 Mobil Oil Corp Herbicidal composition and method of use
US3932509A (en) * 1970-03-23 1976-01-13 Ciba-Geigy Corporation Carbamoyloximes derivatives
US3708590A (en) * 1970-07-02 1973-01-02 Stauffer Chemical Co Method of controlling acarids with certain oxime esters
US3903303A (en) * 1970-07-06 1975-09-02 Stauffer Chemical Co Controlling fungi and bacteria with certain oxime esters
US3819358A (en) * 1971-02-23 1974-06-25 Chemagro Corp Retarding plant growth with cyclohexenone oximes
US4030912A (en) * 1973-04-11 1977-06-21 Hercules Incorporated Certain oximinyl allophanates and their use as herbicides
US4115093A (en) * 1975-10-28 1978-09-19 Hercules Incorporated Certain oximinyl allophanates and their use as herbicides
EP0039308A1 (de) * 1980-04-24 1981-11-04 Ciba-Geigy Ag Cyclobutanonoximcarbamate, Verfahren zu ihrer Herstellung und ihre Verwendung in der Schädlingsbekämpfung sowie die als Zwischenprodukte dienenden Cyclobutanonoxime
US4336199A (en) * 1981-07-10 1982-06-22 Morton-Norwich Products, Inc. 5-(2,4-Dichlorophenyl)-3-furancarboxaldehyde-O-[(methylamino)carbonyl]oxime
US20130019525A2 (en) * 2010-10-05 2013-01-24 Nahum Shpak Plant growth medium
US8984805B2 (en) * 2010-10-05 2015-03-24 Nahum Shpak Plant growth medium
US9260352B2 (en) 2010-10-05 2016-02-16 Nahum Shpak Plant growth medium
US10962652B2 (en) 2010-10-08 2021-03-30 Samsung Electronics Co., Ltd. Determining context of a mobile computer

Also Published As

Publication number Publication date
FR1190302A (fr) 1959-10-12
NL224194A (en(2012))
GB824534A (en) 1959-12-02
NL106827C (en(2012))
CH366690A (de) 1963-01-15
DE1024746B (de) 1958-02-20
BE564131A (en(2012))

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