US3792089A - N-aryl ureas - Google Patents

N-aryl ureas Download PDF

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Publication number
US3792089A
US3792089A US00094534A US3792089DA US3792089A US 3792089 A US3792089 A US 3792089A US 00094534 A US00094534 A US 00094534A US 3792089D A US3792089D A US 3792089DA US 3792089 A US3792089 A US 3792089A
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United States
Prior art keywords
active compound
chloro
compounds
plants
active
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Expired - Lifetime
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US00094534A
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English (en)
Inventor
E Klauke
L Eue
E Kuhle
H Hack
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Bayer AG
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Bayer AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C265/00—Derivatives of isocyanic acid
    • C07C265/12—Derivatives of isocyanic acid having isocyanate groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C275/30—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by halogen atoms, or by nitro or nitroso groups
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
    • Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
    • Y10S516/02—Organic and inorganic agents containing, except water
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
    • Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
    • Y10S516/07—Organic amine, amide, or n-base containing

Definitions

  • the present invention relates to and has for its objects the provision for particular new N-aryl ureas which possess valuable, especially selective, herbicidal properties, active compositions in the form of mixtures of such compounds with solid and liquid dispersible carrier vehicles, and methods for producing such compounds and for using such compounds in a new way, especially for combating weeds, undesired plants, and the like, with other and further objects becoming apparent from a study of the within specification and accompanying examples.
  • N-aryl-N'-alkyl ureas can be used as herbicides. It is further known specifically that N-(3-trifluoromethyl-phenyl)-N',N'-dimethyl urea (A) and N-(4-trifluoromethyl-phenyl)-N',N'-dimethyl urea (B) can be used as selective herbicides (see British Pat. 914,779).
  • N-aryl ureas i.e. N-(3- chloro-4-trifluoromethyl phenyl)-N'-alkyl and N,N- dialkyl-ureas, having the general formula in which R, is selected from the group consisting of hydrogen and alkyl having 1-4 carbon atoms, and R is alkyl having l-4 carbon atoms, exhibit strong herbicidal, in particular selective herbicidal, properties.
  • Suitable amines include methyl, dimethyl, methyl-butyl and isopropyl amine, and the like.
  • solvent this term includes mere diluents
  • solvent these include ethers, such as dioxane and tetrahydrofuran, aromatic hydrocarbons, such as chlorobenzene.
  • reaction temperatures can be varied within a fairly wide temperature range; they are normally substantially between about '0 to 0., preferably from about 20 to 40 C.
  • the particular new N-aryl ureas of the present invention exhibit strong selective herbicidal properties. These compounds can therefore be used for the control of weeds in crops.
  • the instant compounds are particularly useful for the control of weeds in cereal crops, such as wheat, barley and maize.
  • the present invention is especially concerned with control of weeds which grow in cereals.
  • weeds which occur in cereals and which are difficult to control but which are destroyed by the particular new active compounds of the present invention include dicotyledons, such as common chickweed (Stellaria media), mayweed (Matricaria chamomilla), ivy-leaved speedwell (Veronica heaerifolia), knotgrass (Polygonum avz'cultrre), dead nettle (Lamz'um pec.) and monocotyledons, such as silky bentgrass (Apera Spica: venti) and annual bluegrass (Poa annua).
  • dicotyledons such as common chickweed (Stellaria media), mayweed (Matricaria chamomilla), ivy-leaved speedwell (Veronica heaerifolia), knotgrass (Polygonum avz'cultrre), dead nettle (Lamz'um pec.
  • the selectivity of the instant new ureas in cereals is a genuine selectivity. It occurs not only when the present ureas are applied according to the pre-emergence method but also when they are used according to the post-emergence process, that i when the herbicide is contacted directly with the cereal plants.
  • the active compounds according to the instant invention can be utilized, if desired, in the form of the usual formulations or compositions with diluents or extenders, i.e. dispersible carrier vehicles, such as solutions, emulsions, suspensions, emulsifiable concentrates, spray powders, pastes, soluble powders, dusting agents, granules, etc.
  • dispersible carrier vehicles such as solutions, emulsions, suspensions, emulsifiable concentrates, spray powders, pastes, soluble powders, dusting agents, granules, etc.
  • surface-active agents including emulsifying agents and/or dispersing agents, whereby, for example, in the case where water is used as diluent, organic solvents may be added as auxiliary solvents (cf. Agricultural Chemicals, March 1960, pp. 35-38).
  • dispersible liquid diluent carriers including inert organic solvents, such as aromatic hydrocarbons (for instance, benzene, toluene, xylene, etc.), halogenated, especially chlorinated, aromatic hydrocarbons (for instance, chlorobenzenes), paraffins (for instance, petroleum fractions), chlorinated aliphatic hydrocarbons (for instance, methylene chloride, etc.), alcohols (for instance, methanol, ethanol, propanol, butanol, etc.), ethers, ether-alcohols (for instance, glycol monomethyl ether, etc.), amines (for instance, ethanolamine, etc.), amide (for instance dimethyl formamide, etc.), sulfoxides (for instance, dimethyl sulfoxide, etc.), ketones (for instance, acetone, etc.), and/or water; as well as dispersible inert finely divided solid carriers, such as
  • ground ynthetic minerals for instance, highly dispersed silicic acid, silicates, e.g. alkali silicates, etc.; whereas the following may be chiefly considered for use as carrier vehicle assistants, e.g.
  • emulsifying agents such as nonionic and/or anionic emulsifying agents (for instance, polyethylene oxide esters of fatty acids, polyethylene oxide ethers of fatty alcohols, alkyl sulfonates, aryl sulfonates, etc., and especially alkyl arylpolyglycol ethers, magnesium stearate, odium oleate, etc.); and dispersing agents, such as lignin, sulfite waste liquors, methyl cellulose, etc.
  • nonionic and/or anionic emulsifying agents for instance, polyethylene oxide esters of fatty acids, polyethylene oxide ethers of fatty alcohols, alkyl sulfonates, aryl sulfonates, etc., and especially alkyl arylpolyglycol ethers, magnesium stearate, odium oleate, etc.
  • dispersing agents such as lignin, sulfite waste liquors,
  • the active compounds according to the instant invention may be employed alone or in the form of mixtures with one another and/or with such solid and/or liquid dispersible carrier vehicles and/or with other known compatible active agents, especially plant protection agents, such as other herbicides, fungicides, insecticides, bactericides, etc., if desired, or in the form of particular dosage preparations for specific application made therefrom, such as solutions, emulsions, suspensions, powders, pastes, and granules which are thus ready for use.
  • plant protection agents such as other herbicides, fungicides, insecticides, bactericides, etc.
  • carrier composition mixtures suitable for direct application or field application generally contemplate those in which the active compound is present in an amount substantially between about 0.01 and 2.0%, preferably 0.01 and 0.8%, by weight of the mixture.
  • the present invention contemplates over-all compositions which comprise mixtures of a dispersible carrier vehicle such as (l) a dispersible carrier solid, and/ or (2) a dispersible carrier liquid, such as an inert organic solvent and/or water, preferably including a surface-active effective amount of a carrier vehicle assistant, e.g. a surface-active agent, such as an emulsifying agent and/or a dispersing agent, and an amount of the active compound which is effective for the purpose in question and which is generally between about 0.01 and 95%, by weight of the mixture.
  • a dispersible carrier vehicle such as (l) a dispersible
  • the active compound can be used according to the pre-emergence method, i.e. before emergence of the cultivated plants, they are particularly efiective also when used according to the post-emergence method.
  • the amounts of active compounds used for actual application to the agricultural area may be varied within fairly wide ranges, such as for example substantially between about 0.1-5 kg. of active compound per hectare, preferably between about 0.5-3 kg./hectare.
  • the content of active compound in the composition mixture actually applied is, in general, substantially between about 0.1 and 2%, and preferably between about 0.2 and 0.8%, by weight of the mixture as aforesaid, yet the mixture is applied such that the active compounds are used in said amounts between about 0.1-5 kg./hectare.
  • inventive compositions also can be used by the so-called ultra-low-volume process with good success. In this process it is possible to use formulations containing up to of active ingredients or even the active substance alone.
  • the present invention contemplates methods of selectively controlling or combating undesired plants, e.g. weeds and the like, which comprise applying to at least one of (a) such weeds and (b) their habitat, i.e. the locu to be protected, a herbicidally effective amount of the particular active compound of the invention alone or together with a carrier vehicle as noted above.
  • the instant formulations or compositions are applied in the usual manner, for example, by spraying, atomizing, scattering, dusting, watering, sprinkling, and the like, whether for pre-emergence application to the soil or post-emergence application to the weeds.
  • the concentration of the particular active compound utilized alone or in admixture with the carrier vehicle will depend upon the intended application and may be varied within a fairly wide range depending upon the weather conditions, the purpose for which the active compound is used, and the plants which are to be controlled or protected. Therefore, in special cases, it is possible to go above or below the aforementioned concentration ranges.
  • Protective colloid 0.03 parts by weight lignin sulfate Dispel-sing auxiliary: 0:15 parts by weight hydroxyarylsulfonic acid formaldehyde condensate To produce a suitable preparation of the particular active compound, 1 part by Weight of such active compound was mixed with the stated amounts of formulation auxiliaries and the resulting concentrate was then diluted with water to the desired final concentration.
  • EXAMPLE 4 3 5 the amount of active compound applied per umt area Pie-emergence test Solvent: 5 parts by weight acetone Emulsifier: 1 part by weight alkylaryl polyglycol ether To produce a suitable preparation of the particular active compound, 1 part by weight of such active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the resulting concentrate is then diluted with water to the desired final concentration.
  • Seeds of the test plants are soon in normal soil and, after 24 hours, watered with the given active compound preparation. It is expedient to keep constant the amount of water per unit area.
  • the concentration of the active compound in the preparation is of no importance, only being decisive.
  • the degree of damage to the test plants is determined and characterized by the values 0-5, which have the following meaning:
  • R represents hydrogen; or alkyl having 1-4 carbon atoms
  • R represents alkyl having 1-4 carbon atoms, as defined above, such as methyl to tert.-buty1 inclusive, and the like, particularly C alkyl.
  • R represents hydrogen or the same C especially C alkyl as R
  • the instant compounds possess total herbicidal action when used in large quantities, although selective herbicidal action is obtained when 13 used in smaller quantities.
  • weeds is meant to include not only weeds in the narrow sense, but also in the broad sense, whereby to cover all plants and vegetation considered undesirable for the particular purposes in question.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
US00094534A 1967-08-12 1970-12-02 N-aryl ureas Expired - Lifetime US3792089A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF0053224 1967-08-12

Publications (1)

Publication Number Publication Date
US3792089A true US3792089A (en) 1974-02-12

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US00094534A Expired - Lifetime US3792089A (en) 1967-08-12 1970-12-02 N-aryl ureas

Country Status (13)

Country Link
US (1) US3792089A (enrdf_load_stackoverflow)
AT (1) AT293783B (enrdf_load_stackoverflow)
BE (1) BE719349A (enrdf_load_stackoverflow)
CA (1) CA943559A (enrdf_load_stackoverflow)
CH (1) CH497392A (enrdf_load_stackoverflow)
DK (1) DK119763B (enrdf_load_stackoverflow)
ES (1) ES357193A1 (enrdf_load_stackoverflow)
FR (1) FR1576193A (enrdf_load_stackoverflow)
GB (1) GB1232038A (enrdf_load_stackoverflow)
IL (1) IL30291A (enrdf_load_stackoverflow)
MY (1) MY7200044A (enrdf_load_stackoverflow)
NL (1) NL6811378A (enrdf_load_stackoverflow)
SE (1) SE331676B (enrdf_load_stackoverflow)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4039315A (en) * 1970-01-24 1977-08-02 Bayer Aktiengesellschaft N-(Difluorochloromethylmercaptophenyl)ureas as herbicides

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4039315A (en) * 1970-01-24 1977-08-02 Bayer Aktiengesellschaft N-(Difluorochloromethylmercaptophenyl)ureas as herbicides

Also Published As

Publication number Publication date
CH497392A (de) 1970-10-15
ES357193A1 (es) 1970-02-16
GB1232038A (enrdf_load_stackoverflow) 1971-05-19
BE719349A (enrdf_load_stackoverflow) 1969-02-12
IL30291A0 (en) 1968-09-26
NL6811378A (enrdf_load_stackoverflow) 1969-02-14
SE331676B (enrdf_load_stackoverflow) 1971-01-11
CA943559A (en) 1974-03-12
DE1668003B2 (de) 1975-09-18
DE1668003A1 (de) 1971-12-09
FR1576193A (enrdf_load_stackoverflow) 1969-07-25
AT293783B (de) 1971-10-25
MY7200044A (en) 1972-12-31
IL30291A (en) 1972-05-30
DK119763B (da) 1971-02-22

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