IL30877A - Herbicidal compositions containing 4-trifluoromethyl-phenyl ureas - Google Patents

Herbicidal compositions containing 4-trifluoromethyl-phenyl ureas

Info

Publication number
IL30877A
IL30877A IL30877A IL3087768A IL30877A IL 30877 A IL30877 A IL 30877A IL 30877 A IL30877 A IL 30877A IL 3087768 A IL3087768 A IL 3087768A IL 30877 A IL30877 A IL 30877A
Authority
IL
Israel
Prior art keywords
formula
herbicidal compositions
compound
agents
compositions containing
Prior art date
Application number
IL30877A
Other versions
IL30877A0 (en
Original Assignee
Ciba Geigy Ag
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from CH1596367A external-priority patent/CH490800A/en
Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag
Publication of IL30877A0 publication Critical patent/IL30877A0/en
Publication of IL30877A publication Critical patent/IL30877A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42—Amides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/02—Suppositories; Bougies; Bases therefor; Ovules
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/005—Antimicrobial preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
    • C07C273/1809—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety
    • C07C273/1818—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety from -N=C=O and XNR'R"
    • C07C273/1827—X being H
    • 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
    • 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
    • C07C275/38—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 doubly-bound oxygen atoms
    • 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
    • C07C275/64—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 singly-bound to oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C335/04—Derivatives of thiourea
    • C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D203/16—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with acylated ring nitrogen atoms
    • C07D203/20—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with acylated ring nitrogen atoms by carbonic acid, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/34—One oxygen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/14—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D263/18—Oxygen atoms
    • C07D263/20—Oxygen atoms attached in position 2
    • C07D263/26—Oxygen atoms attached in position 2 with hetero atoms or acyl radicals directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
    • C07D265/32—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings with oxygen atoms directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C07D277/82—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C07D285/135—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
    • C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0084—Antioxidants; Free-radical scavengers

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Birds (AREA)
  • Dermatology (AREA)
  • Biochemistry (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

η κ»-ηκ ■» 3ό Herbicidal compositions containing 4-trifiuoromethyl-phenyl ureas CIBA-GBIGY A.G.
G : 29097 2 - 30877/2 The present invention provides selective herbicidal compositions which contain, as the active ingredients a compound of the general formula in which: either Y is hydrogen and is a-butyl, methoxy or isobuty-nyl or Y is chlorine and is methoxy, isobutynyl or propargyl; together with one or more solid or liquid additives, such as: solvents, dispersing agents, emulsifiers, wetting agents, adheslves, thickeners. furthermore the compositions may also contain other known biocldal agents, e.g. fungicides, bactericides, herbicides, acaricides, insecticides, and optionally also fertilizers.
In principle all formulations known to the art can be used for the production of the new herbicidal compositions.
Thus, the active ingredients of formula I can be used for controlling undesired plant growth in the form of powders, emulsions, suspensions, solutions or preferably granulates.
The amounts to be applied are between 0.1 and 10 kg of active substance per hectare, advantageously betwen 0.5 kg and 5/per hectare.
The compositions are useful especially for protecting plant cultures such as maize, rice, cotton, soya, grain or sugar beets. Surprisingly the novel compositions " 5 " 30877/2 containing the active ingredients of formula I possess a much more pronounced seleotivity as compared with compositions containing active ingredients of similar structure, the effect being exhibited both in the pre-emergent and post-emergent procedure. 4-halo-3-trifluoromethylphenyl ureas are known from the Israeli Patent Speci ication No* 14217, but they possess unsatisfactory activities and are apt to damage culture plants such as those listed above. Only in particular cases and by applying precisely adjusted amounts of those known active substances could some degree of selectivity be attained. In practice, however, such a risk cannot feasibly be taken. As contrasted thereto, the novel compositions according to this invention exhibit a selectivity which is more sharply defined, both in respect of the culture plants and the undesired weeds, and this within a greater range of applicated amounts.
The active phenyl ureas of formula I above can also be combined with other known herbicides which assist or supplement the action of the former. The herbicides known e.g. from U S. Patent Specification No. 3,385,692, or growth hormones are suitable for this purpose.
The compounds of formula I can be prepared by methods known per se: a) by the action of an aromatic compound of the general formula - 4 - 30877/2 in which Ϊ has the same meaning as in formula I above and A is a group -ITO-COQR· , -UH-CO-halogen ondary same meaning as in formula Z above, or b) by reaction of an ^aniline of the general formula in which Y has the same meaning as above with a compound of the formula in which has the same meaning as in formula I and R' is alkyl or phenyl. 30877/2 Thus, for example the compound of the formula ca be prepared according to the ollowing example.
EXA PltE 1 100 ml of Ν,Ο-Dimeth lhydroxylaj-iine are dissolved in 2 1 of petroleum-ether (boiling point 50° to 70°C) and the solution is introduced into a 4i 1 flask. To the solution 222 g of 3-cliloro-4-trlfluoromethyl-phenylisocyanate in 100 ml of petroleum-ether (boiling point 50° to 70°C) are added dropwlse. The mixture is stirred overnight and the resulting precipitate is filtered off. 2§8 g of Mi¾-meth l-N'-methoxy-N-(3-^chlor0-4-trifluoromethyl-phenyl) urea (compound No. 1) are obtained. Μ.Ρ» (after recrystalli-zatlon) 63° to 65°C.
The following compounds of formula I were obtained according to the procedure of Example 1 or another one of the above mentioned processes: Compound Uo. X H.P, (°0) Ri 2 H -CH-CaCH 120 - 121 CH-. j 3 H -G4H9(n) 65 - 66 4 H -0CH3 94 - 95 01 -CH2-G≡CH 90.5 - 92 6 01 -GE-C¾3H 121 - 122 CH_ 3 - 6 - 50877/2 EXAMPLE 2 "Dusting powder; In order to produce a water soluble dusting powder the following components are mixed and finely ground; 50 parts of an active substance of formula I parts of highl adsorbent silicic acid parts of bolu alba (kaolin) 1.5 parts of sodium l-benzyl-2-stearyl-benzimidazole-6,3- : . disulfonate 3.5 parts of the condensation product of p-tert.-octylphenol and ethylene oxide.
EXAMPLE 3 Emulsion concentrates: a) 40 ^arts of an active substance of formula I are mixed with 10 parts of a mixture of an anionic surfactant, preferably the calcium or magnesium salt of monolauryl- sulf©benzene monosulfonic acid and a monionic surfactant, preferably a polyethyleneglycol ether of monosorbitol , laureate, and the entire mixture is dissolved in a small s amount of xylene. The mixture is then made up with xylene to a volume of 100 co and a clear solution Is obtained which can be used as a concentrate or a spray composition and, when added into water, it yields a stable emulsion. b) Those active substances which have a good water solubility can also be formulated as emulsion concentrates according to the following procedure: > - 7 - 30877/2 parts of activ-e substance 70 parts of xylene parts of a mixture consisting of the condensation product of an alkylpheriol with ethylene oxide and of calcium dodecylbenzenesulfonate are mixed together. Dilution w th water to the desired concentration results in a" spray-able emulsion.
EXAMPLE 4 Granulates ; a) 7.5 g of an active substance of formula I are dissolved in 100 cc of acetone and this solution is added to 92 g of granulated Attapulgit (mesh width 24/48 mesh/inch). After thorough mixing, the solvent is removed in a rotatory evaporator. granulate containing 7<,5f° of active substance is obtained. < b) For manufacturing a 10f<> polymer-granulate, 1050-1100 g of an active substance of formula I (technical grade) are dissolved in 2 1 of trichloroethylene and sprayed at 1.5 atm-gauge onto 9320 g of a porous urea-formaldehyde granulate in a fluidized bed granuletor. By heating the fluidizing air to about 50°C the solvent can be separated and recovered. c) For manufacturing a 7·5% heavy granulate,- 770 g o a solid granulate of an active substance of formula I (technical grade), 500 g of BaSO^, 1000 g of urea and 7730 g of powdered porous polyacrylonitrile are irst compressed and subsequently comminuted to the desired grain size - 8 - 30877/2 EXAMPLE jHerbicidal activity: Culture plants and weeds were seeded in earthenware pots in the greenhouse. The active substanoes to be tested were applied pre-emergently one day after the seeding as aqueous emulsioce in amounts corresponding to 2 kg per hectare and 1 kg per hectare of active substance and evaluated three weeks after seeding, In the post-emergence procedure aqueous emulsions of the active substances were applied one week after seeding, when the dicotyledonous plants used in tie experiments had developedjto the three-leaf stage. The amounts applied were 2 kg of active substance per hectare and 1 kg per hectare. The results were evaluated 12 days after applicatio of the active substance.
M' ,E*-dimethyl-N-(4-chloro-3- rifluoromethyipheny1) urea (compound B) known f om the Israeli Patent Specification No. 14217 was used for comparison.
The results are shown in the following Tables I and II: TABLE I - Pre-emergence procedure - 11 - 30877/2 legend t 1-3 no or only passing damage of the plant 4-6 medium damage 7-8 heavy damage 9 plant totally damaged.
It can be seen from the tables that the selectivity of the known compound B is considerably lower with respect to the important culture plants, grain, maize, rice, soya and cotton than the selectivity of the compounds of formula I according to this invention.
EXAMPliB 6 The selective herbididal activity of compound 1 of this invention was compared with the compound .·..
(Compound A ) disclosed in Israeli Patent Specification No. 30291, which was not published prior to the present invention. - 12 - 30877/2 Control of Digit-aria sanquinalis in sugarcane Trial carried out post-emergence in Brazil.
Control of Panicum spp. in sugarcane and citrus , fBrazil and South Africa) and Sporobolus sp. grass (on an industrial site).
• Trial methods ! Trial e:)was a screening trial,' with plots 4 sq.m., un- roplicutod, when weeds wore 2 - 4 cm. tall. ' I The other trials were all done on plots between 15 and. ! 50 s.q.m., 4 times replicated. The sugarcane plots were I ' i j arranged so that each had 2 or J rows of carie in citrus, - 14 - 30877/2

Claims (2)

1. Selective herbicidal compositions containing as an active ingredient a compound of the general formula in which: either Y is hydrogen and R^ is n-butyl, methoxy or isobuty^ nyl; or Y is chlorine and is methoxy, isobutynyl or propargyl; together with one or more solid o liquid additives, such as: solvents, dispersing agents, emulsifiers, wetting agents, adhesives, thickeners. Furthermore the compositions may also contain other known biocidal agents, e.g. fungicides, bactericides, herbicides, acarlcides, insecticides, and optionally also fertilizers.
2. Herbicidal compositions according to Claim 1 and containing one or more of the following additives: solvents, dispersing agents, emulsifiers, wetting agents, adhesives, thickeners and furthermore also other biocidal agents. 3· Herbicidal compositions according to Claim 1 or 2, wherein the active ingredient is the compound of the formula
IL30877A 1967-10-17 1968-10-15 Herbicidal compositions containing 4-trifluoromethyl-phenyl ureas IL30877A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH1446267 1967-10-17
CH1596367A CH490800A (en) 1967-11-15 1967-11-15 New biocidal agent in a commercial form and its use

Publications (2)

Publication Number Publication Date
IL30877A0 IL30877A0 (en) 1968-12-26
IL30877A true IL30877A (en) 1973-06-29

Family

ID=25714504

Family Applications (1)

Application Number Title Priority Date Filing Date
IL30877A IL30877A (en) 1967-10-17 1968-10-15 Herbicidal compositions containing 4-trifluoromethyl-phenyl ureas

Country Status (8)

Country Link
BE (1) BE722372A (en)
DE (1) DE1802739A1 (en)
ES (1) ES359234A1 (en)
FR (1) FR1593586A (en)
GB (1) GB1250624A (en)
IL (1) IL30877A (en)
NL (1) NL6814810A (en)
OA (1) OA02904A (en)

Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH505543A (en) * 1968-11-01 1971-04-15 Ciba Geigy Ag Pesticides
ZA706704B (en) * 1969-10-16 1972-05-31 Lilly Co Eli Immunosuppresants and anti-viral agents
BE788983A (en) * 1971-09-22 1973-01-15 Rolland Sa A 3-TRIFLUOROMETHYLANILIDES
ATE107280T1 (en) * 1988-04-15 1994-07-15 Taiho Pharmaceutical Co Ltd CARBAMOYL-2-PYRROLIDINONE COMPOUNDS.
DE19632005A1 (en) * 1996-08-08 1998-02-12 Bayer Ag Substituted p-trifluoromethylphenyluracile
SK282727B6 (en) * 1997-12-19 2002-11-06 Slovakofarma, A. S. 1,3-Disubstituted ureas - ACAT inhibitors and method of preparing
SE9903894D0 (en) * 1999-10-28 1999-10-28 New Pharma Research Ab Novel compounds
NZ540612A (en) 2003-01-14 2008-02-29 Arena Pharm Inc 1,2,3-Trisubstituted aryl and heteroaryl derivatives as modulators of metabolism and the prophylaxis and treatment of disorders related thereto such as diabetes and hyperglycemia
AR045047A1 (en) 2003-07-11 2005-10-12 Arena Pharm Inc ARILO AND HETEROARILO DERIVATIVES TRISUSTITUIDOS AS MODULATORS OF METABOLISM AND PROFILAXIS AND TREATMENT OF DISORDERS RELATED TO THEMSELVES
DOP2006000010A (en) 2005-01-10 2006-07-31 Arena Pharm Inc PROCEDURE TO PREPARE AROMATIC ETERES
MY148521A (en) 2005-01-10 2013-04-30 Arena Pharm Inc Substituted pyridinyl and pyrimidinyl derivatives as modulators of metabolism and the treatment of disorders related thereto
WO2009087981A1 (en) * 2008-01-11 2009-07-16 Kri Inc. Polymerizable compound and method for producing the same
US10894787B2 (en) 2010-09-22 2021-01-19 Arena Pharmaceuticals, Inc. Modulators of the GPR119 receptor and the treatment of disorders related thereto
CA2862417C (en) * 2012-01-06 2017-09-05 Abide Therapeutics, Inc. Carbamate compounds and of making and using same
RU2487132C1 (en) * 2012-07-23 2013-07-10 Общество с ограниченной ответственностью "Метаген" Cyclic 5-nitropyridin-2-yl-thioalkenyl-4-dithiocarbamate derivatives having antifungal activity and use thereof
UA126268C2 (en) 2015-01-06 2022-09-14 Арена Фармасьютікалз, Інк. Methods of treating conditions related to the s1p1 receptor
ES2878041T3 (en) 2015-03-18 2021-11-18 H Lundbeck As Piperazine Carbamates and Methods to Prepare and Use Them
EA201792496A1 (en) 2015-05-11 2018-04-30 Абиде Терапеутикс, Инк. METHODS OF TREATMENT OF INFLAMMATION OR NEUROPATHIC PAIN
CA3002551A1 (en) 2015-06-22 2016-12-29 Arena Pharmaceuticals, Inc. Crystalline l-arginine salt of (r)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclo-penta[b]indol-3-yl)acetic acid(com pound 1)for use in s1p1 receptor-associated disorders
US10463753B2 (en) 2016-02-19 2019-11-05 Lundbeck La Jolla Research Center, Inc. Radiolabeled monoacylglycerol lipase occupancy probe
US11000037B2 (en) * 2016-07-18 2021-05-11 Oat Agrio Co., Ltd. Benzylamide compound, method for producing the same, and miticide
JP7042804B2 (en) 2016-09-19 2022-03-28 ルンドベック ラ ホーヤ リサーチ センター，インク． Piperazine carbamate, and how to make and use it
JOP20190105A1 (en) 2016-11-16 2019-05-09 Lundbeck La Jolla Research Center Inc Magl inhibitors
JOP20190106A1 (en) 2016-11-16 2019-05-09 Lundbeck La Jolla Research Center Inc Magl inhibitors
MX2020012158A (en) 2018-05-15 2021-01-29 H Lundbeck As Magl inhibitors.
CN110054577B (en) * 2019-05-05 2021-09-10 中国医学科学院放射医学研究所 Compound containing urea and thiourea structure, synthetic method and application thereof
BR112021025516A2 (en) 2020-04-21 2022-11-01 H Lundbeck As PROCESSES FOR MANUFACTURING 1,1,1,3,3,3-HEXAFLUOROPROPAN-2-ILA 4-(2-(PYRROLIDIN-1-IL)-4-(TRIFLUOROMETHYL)BENZYL)PIPERAZINE-1-CARBOXYLATE AND SAME MONOCHLORIDATE SALT FORM 2
CN116239551B (en) * 2022-12-05 2024-07-26 湖北大学 Furanylurea compound with molluscicidal activity and preparation and application thereof

Also Published As

Publication number Publication date
FR1593586A (en) 1970-06-01
NL6814810A (en) 1969-04-21
ES359234A1 (en) 1970-06-01
IL30877A0 (en) 1968-12-26
DE1802739A1 (en) 1969-06-04
BE722372A (en) 1969-04-16
GB1250624A (en) 1971-10-20
OA02904A (en) 1970-12-15

Similar Documents

Publication Publication Date Title
IL30877A (en) Herbicidal compositions containing 4-trifluoromethyl-phenyl ureas
JPH0228159A (en) Heterocyclic 2-alkoxyphenoxysulfonyl urea, its production and use thereof as herbicide or plant growth control agent
US3676441A (en) 2-amino-4-tertiary butylamino-1,3,5-triazines
JPH0327359A (en) New herbicide
JPS584757A (en) Substituted cyclopropylmethoxyurea, herbicidal composition and weeding method
JPS62249903A (en) Defoliating agent containing thiadiazolyl urea
HU176584B (en) Herbicide preparation containing of active mateirals of two types
JPS62205063A (en) Novel 2-cyanobenzoimidazole derivative, manufacture, use as germicide and combination with other germicides
JPS60166668A (en) 2-alkoxyaminosulfonylbenzene-sulfonylurea derivative, preparation thereof and herbicide
JPS61186394A (en) N-(phosphonomethylglycyl)sulfonylamine type herbicide
US3210423A (en) N, n&#39;-di(tetra-substituted-phenyl)-diaminomethanes
KR102059979B1 (en) Herbicidal composition
JPS5844643B2 (en) Shinkinadjiyosouzai
HU193705B (en) Selective herbicidal compositions of prolonged effect, containing alpha-chlorine-acetamide-derivatives as active substance
JPS6338995B2 (en)
JPS61291573A (en) 2-phenyl-4,5,6,7-tetrahydro-2h-indazole derivative, production thereof and herbicide
US3244714A (en) Carbamoyl pyridazines
US3676459A (en) 3-arylimino-1,2-dithiols
JPS5837281B2 (en) Shinkinadjiyosouzai
JPS62263178A (en) Sulfonyl urea type herbicide, its production, composition containing the same and its use
NO140382B (en) TIADIAZOLYLIMIDAZOLIDINONES WITH HERBICIDING EFFECT
JPS637534B2 (en)
SU287643A1 (en)
US3484525A (en) Process of controlling fungi with 1,3-diaryl-imino-hydantoins
JPH01160961A (en) Nicotine derivative for fungicide