GB2028811A - Phenoxy butanes and derivatives - Google Patents

Phenoxy butanes and derivatives Download PDF

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GB2028811A
GB2028811A GB7927060A GB7927060A GB2028811A GB 2028811 A GB2028811 A GB 2028811A GB 7927060 A GB7927060 A GB 7927060A GB 7927060 A GB7927060 A GB 7927060A GB 2028811 A GB2028811 A GB 2028811A
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covalent bond
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
    • C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
    • C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
    • 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
    • A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
    • 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
    • A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
    • A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
    • 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
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/10—Sulfones; Sulfoxides
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/20—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom three- or four-membered rings
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
    • A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
    • A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
    • A01N43/30—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
    • 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
    • A01N49/00—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds containing the group, wherein m+n>=1, both X together may also mean —Y— or a direct carbon-to-carbon bond, and the carbon atoms marked with an asterisk are not part of any ring system other than that which may be formed by the atoms X, the carbon atoms in square brackets being part of any acyclic or cyclic structure, or the group, wherein A means a carbon atom or Y, n>=0, and not more than one of these carbon atoms being a member of the same ring system, e.g. juvenile insect hormones or mimics thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
    • C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
    • C07C205/37—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/06—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton from hydroxy amines by reactions involving the etherification or esterification of hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C315/00—Preparation of sulfones; Preparation of sulfoxides
    • C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
    • C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
    • C07C43/29—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring 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 atoms of the carbocyclic ring
    • C07D317/64—Oxygen atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Environmental Sciences (AREA)
  • Dentistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Insects & Arthropods (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
  • Epoxy Compounds (AREA)

Abstract

The invention provides 1,4-diphenoxybutanes, e.g. 1-(3,4- dichlorophenoxy)-4-[( alpha , alpha , alpha -trifluoro -m-tolyl)oxy]-butane. The compounds bear at least one trifluoromethyl in one of both phenoxy substituents and are useful as herbicides.

Description

SPECIFICATION Phenoxy butanes and derivatives The present invention relates to bis-phenoxy hydrocarbon derivatives, their use as herbicides and herbicidal compositions containing the same.
More specifically the present invention provides compounds of formula I,
wherein X and X' are independently H, fluoro, chloro, bromo, CF3, C1-C4 alkyl, C,-C4 alkoxy, C1-C4 alkylthio, nitro, cyano, amino, mono-C1-C4 alkylamino, di-C1-C4 alkylamino, C1-C4 alkylsulphonyl, or C1-C4alkylsulphinyl, or X is as above defined and X' is phenoxy or phenoxy mono- or di-substituted by fluoro, chloro, bromo, CF3, C,-C4 alkyl or C1-C4 alkoxy, Y and Y' are independently H, fluoro, chloro, bromo, CF3, C1-C4 alkyl, C1-C, alkoxy, C1-C4 alkylthio or nitro, or X and Y and/or X' and Y' together form C1-C2 alkylenedioxy on adjacent ring carbon atoms Z is H, fluoro, chloro, bromo, Cf3 or C1-C4 alkyl, R and R5 are independently H, Ct-C4 alkyl or -COOR3 wherein R3 is H or C1-C4 alkyl, R1 and R3 are independently H, C1-C5 alkyl, fluoro, chloro, bromo or hydroxy, and R2 and R4 are independently H or Ct-C3 alkyl or both together form a covalent bond or an epoxy bridge (-0-), with the proviso that no two adjacent ring substituents in either rings a orp are from the group of t-butyl, t-butoxy and CF3.
The invention also provides processes for the production of compounds of formula I comprising a) condensing a compound of the formula II and/or II,'
wherein X, Y, X', Y' and Z are as above defined, with an aliphatic hydrocarbon derivative of the formula Ill,
wherein R, Rt, R3, R3, R4 and R5 are as above defined and Q is a leaving group displaceable under phenolic hydroxy condensing conditions, and Q' is either i) a leaving group displaceable under phenolic hydroxy condensing conditions or ii) a radical of the formula
wherein X, Y, X', Y' and Z are as above defined, with the proviso that at least one of the reactants II, II' or Ill contains the B' radical, b) in order to prepare compounds of formula I in which R2 and R4 are both H reducing the double bound in the 2-butene group of a compound of the formula 1',
wherein X, Y, X', Y', ZR, Rt, R3 and R5 are as above defined, with an alkene reducing system, or c) in order to prepare compounds of the formula 1",
wherein X, Y, X', Y', R, Rt, R3 and Rs are as above defined, epoxylating the double bound in the butene group of a compound of the formula 1', above stated.
The process a) may be effected in an appropriate organic solvent, e.g. dimethylformamide, or in an aqueous/organic solvent, e.g. water/toluene, and a phase transfer catalyst, e.g. benzylammonium chloride. The reaction is preferably effected in the presence of a base, e.g. an alkali such as KOH, alkali metal carbonate such as Na2CO3 or a metal hydride such as NaH. The reaction may be effected over a wide range of temperatures, e.g. 15-100"C. Typical leaving groups for 0 and 0' are chloro, bromo, iodo, methanesulphonate and p-toluenesulphonate. As will be appreciated, the yields obtained will depend on the relative amounts of the reactants and on the nature of the group Q'.Thus, when Q' is a leaving group, one mol of a compound of formula Ill is either reacted with about 2 mols of a compound of formula II or II' (variant 1) or with a more or less equal molar mixture of compounds offormula II and II' (variant 2). Symmetric compounds of formula I are preferably prepared according to variant 1, asymmetric compounds of formula I preferably according to variant 2. Separation of mixtures that may be formed in process a) may be effected by known procedures such as chromatography, fractional crystallization and the like, particularly gas chromatography.
Process b) may be effected in a solvent such as ethyl acetate with an alkene reducing system or agent such as by catalytic hydrogenation, e.g. employing palladium, platinum or Raney nickel as catalyst, or diborane. The reaction may be carried out at, e.g. 0 C to 100"C, and is preferably effected at room temperature.
Process c) may be effected in a solvent such as acetic acid, chloroform or methylene chloride, employing a peracid, e.g. peracetic acid or m-chloroperbenzoic acid, as epoxylating agent at temperatures of, e.g. 0 C to 1 00 C, and preferably at room temperature.
The starting materials and reagents employed in the processes described above, e.g. compounds of the formulae II and Ill are either known or, insofar they are not known, they may be prepared in an analogous mannerto the processes for the produc- tion of the known compounds.
The compounds of the formula III in which Q' is a radical of the formula B or B' may, for example, be produced by reacting 1 mol of a compound Ill in which Q' is a leaving group with one mol of a phenol of the formula II or II', in a manner analogous to process a). Mixtures of the product compounds Ill that may result from such reactions, may be separated by established procedures, e.g. gas chromatography. In general, the separation is, when desired, preferably effected at this time, i.e. before the compound lil is further reacted with a compound II or 11'.
Geometric isomerism is possible in compounds I in which R3 and R4 form a covalent bond or an epoxy bridge, and in corresponding intermediates and starting materials therefor. The particular geometric forms of such intermediates and starting materials are generally unaffected by the reaction conditions described herein and will appear in the final products. When mixtures of geometric isomers are produced, it is, as a practical matter, generally preferred to employ such mixtures as such in the herbicide method and compositions of the invention, even though separation may be effected by known procedures.
The compounds of formula I are useful as herbicides as indicated by the damage caused to undesired plants such asAmaranthus retroflexus, Capsella bursa pastoris, Apera spica venti, Chenopodium album, Galium aparine, Stellaria media, Senecio vulgaris, Echinochloa crus galli, Alopecurus myosuroides, Avena fatua, Agrostis alba after pre- and post-emergence greenhouse treatment with test dosages equivalent to 0.2, 1.0 and 5.0 kg of active agent/hectare of treated surface. The determination of the herbicidal effect is made 28 days after treatment. During the test, the greenhouse is kept at a temperature of 20 to 24"C and exposed to 14 to 17 hours daylight a day.As under similar greenhouse conditions no substantial damage to certain crops such as cereal (wheat, barley etc), corn and carrots was observed with dosages up to 5.0 kg/ha of active agent, the compounds of formula I are also indicated for use as selective herbicides in a crop locus, particularly in a crop locus as mentioned above.
The present invention therefore also provides a method of combating weeds, particularly in a crop locus, especially in a cereal, corn or carrot crop locus, particularly in a wheat or corn locus and especially a wheat locus.
The amount to be applied to attain the desired effect will vary depending on the particular crop if employed for selective use and other standards such as the compound employed, mode of operation, conditions of treatment and the like.
In general, however, satisfactory total weed control may be obtained at application rates of from 0.1 to 20 kilograms per hectare of treated area. The compounds of formula I generally exhibit greater potency in post-emergence application which is a preferred contemplated mode of application at rates preferably of 0.1 to 12 kilograms per hectare.
For selective weed control, in general, satisfactory results are usually obtained in the range from about 0.1 to 7.0 kg/ha, preferably from about 0.2 to 5.0 kg/ha, more preferably from about 0.5 to 3.5 kg/ha, the application being repeated if necessary. The post-emergence application is preferred.
The emergence time referred to above is with respect to the weeds. In the preferred post emergence selective use the compounds I may be applied pre-emergence the crop but it is generally preferred to effect the application post-emergence both the weeds and crop.
The generally preferred compounds of the formula I (herein called formula la) have one and preferably more or all of the following features: A) the (depicted) CF3 fixed atthe3-position (meta position) of Ring a); B) X and X' being H, fluoro, chloro, bromo, CF3, C,-C4alkyl, C1-C4alkoxy, C1-C4alkylthio, nitro, cyano or amino; C) Y being H; D) Y' being H, fluoro, bromo, chloro, bromo, CF3, C1-C3alkyl, nitro, C1-C3alkoxy, and C1-C3alkylthio; E) Z being H,fluoro, CF3, chloro or bromo; F) R, R1, R3 and R5 being H or C1-C4alkyl; and G) R2 and R4 being both H or together forming a covalent bond.
Within the scope of the generally preferred compounds described above are the generally more preferred compounds of the formula I (herein called formula lb) that have one and preferably more or all of the following features: A) X being H, fluoro, chloro, bromo and CF3; B) X' being H, fluoro, chloro, bromo, CF3, C1-C4alkyl, C1-C4alkoxy, C1-C4alkylthio and nitro; C) Z being H; and D) R, R1, R3 and R5 all being H or at least one but not more than two being C1-C4alkyl.
Particularly preferred sub-groupings within the scope of the compounds I, la and lb are those in which one of R1 and R3 is H and the other C1-C4alkyl, more preferably C1-C3alkyl, particularly methyl or ethyl, especially ethyl, and more particularly those in which R3 is H and R1 is C1-C4alkyl, more preferably C1-C3 alkyl, particularly methyl or ethyl and especially ethyl. A general preference for those compounds I in which R2 and R4 are both H is also indicated.
A most preferred sub-grouping of the compounds Ibis represented by the formula Ic,
wherein X is H, fluoro, chloro, bromo, CF3, nitro or C1-C3 alkyl, Y is H, fluoro, chloro, bromo or CF3, one of R 1 and R 3 is C1-C3alkyl, particularly methyl or ethyl, especially ethyl, and the other H, and R2 and R 4 are either both H or together form a covalent bond.
Within the scope of the compounds Ic it is generally preferred that R 1 be C1-C3alkyl, particularly methyl or ethyl, especially ethyl, and R 3 be H, and that such compounds in which R 1 is C1-C3alkyl, particularly methyl or ethyl, especially ethyl, and R 3 is H also have R 2 and R4 are each H.
The compounds may be employed as herbicidal compositions is associated with bioiogically inert herbicide carriers. Such compositions also form part of the present invention.
Herbicidal compositions may be employed in either solid or liquid application forms. Solid forms, e.g. dusting forms and granulates, may be produced by mixing or impregnating solid herbicide carriers such as diatomaceous earth, kaolin, talc, chalk, limestone and cellulose powder, with the compounds.
Additives may be employed in the herbicidal composition. Typical of such additives are wetting and dispersing agents, e.g. the condensation product of formaldehyde with naphthalene sulphonate, and alkyl benzene sulphonates, adhesion imparting agents, e.g. dextrin, and emulsion stabilizers, e.g.
ammonium caseinate. Such additives are suitable for incorporation into, e.g. a wettable powder form of composition or together with suitable solvents, e.g. hydrocarbons such as benzene, toluene, xylene, tetrahydronaphthalene, alkylated naphthalenes, kerosene, aromatic petroleum hydrocarbon fractions (e.g. commercial product Shellsol AB having b.pt.
range 187-213"C), ketonessuch as isophorone, acetone, cyclohexanone, di-isobutylketone and methylethylketone, alcohols such as isopropanol, ethanol, and methylcycloyhexanol, chlorinated hydrocarbons such as tetrachloroethylene, ethylene chloride ortrichloroethylene, to form emulsion concentrates.
The herbicidal compositions may contain, aside from a compound of formula I as active agent, and an inert herbicide carrier, other active agents, such as herbicides.
Concentrate forms of composition generally contain between 2 and 80%, preferably between 2 and 500/a, by weight of a compound of formula I as active agent.
Application forms of composition generally contain between 0.01 and 10%, by weight of a compound of formula I as active agent.
Specific Examples of herbicidal compositions will now be described.
Example A Wettable Powder 25 Parts of a compound of formula I, e.g. 1, 4 - bis [(a, a, a - trifluoro - m - tolyl) oxy] - 2 - butene (cis), 5 parts of a condensation product from formaldehyde and naphthalene sulphonate, 2 parts of alkyl benzene sulphonate, 5 parts of dextrin, 1 part of ammonium caseinate and 62 parts of diatomaceous earth are mixed until a homogeneous mixture is obtained and then ground until the particles are considerably smaller than 45 microns as an average.
Example B Emulsion Concentrate 25 Parts of a compound of formula I, e.g. 1(3,4 dichlorophenoxy) - 3 - methyl - 4 - [a, a, a - trifluoro - m - tolyi) oxyj - butane, 65 parts of xylene and 10 parts of the mixed reaction product of a n an alkylphenol with ethylene oxide and calcium - dodecylbenzene sulphonate are thoroughly mixed until a homogeneous solution is obtained. The resulting emulsion concentrate is diluted with water before use.
Example C Granulate 5 Kg of a compound of formula I, e.g. 1, 4 - bis - [(a, a, trifluoro - m - tolyl) oxyj - 2,3 - epoxy butane are dissolved in 25 1 methylene chloride. The solution is then added to 95 kg of granulated attapulgate (mesh size 24/48 mesh/inch) and thoroughly mixed.
The solvent is then evaporated off under reduced pressure with warming.
The invention is illustrated by the following Exam ples wherein parts and percentages are by weight and temperatures are in "C.
Example 1 1,4 - bis - [(ex, a - trffluoro - m - tolyl) oxy] - cis - 2 -butene -- Process a) 3.24 g (0.02 i\A) of m - hydroxy - benzotrifluoride are added to 30 ml of dimethylformamide containing 1.68 g (0.03 M) of potassium hydroxide. The solution is maintained at room temperature with a water bath as 2.14 g (0.01 M) of tis - 1,4- dibromo - 2 - butene are slowly introduced. The ensuing yellow mixture is stirred for 2 hours and then poured into water. After extraction with ether, washing with water and evaporating off the solvent, a yellow oil is obtained.
The oil is chromatographed on a silica gel column employing n-hexane/ethylacetate (24:1) as elba nut to yield the title product m.pt. 50-51'.
Example 2 1- (3,4 - dichlorophenoxy) - 4 - [(a a a- - Trifluoro - m - tolyl) oxy] - butane - Process a) 0.60 g (0.010 M) of potassium hydroxide and 1.13g (0.007 M) of m - hydroxy - benzotrifluoride are added to 15 ml of dimethylformamide and the mixture stirred until the reagents have dissolved. 2.1 g (0.007 M) of 1 - bromo - 4 - (3,4 - dichloro phenoxy) - butane are introduced dropwise and the mixture stirred at room temperature for 1 hour. The resulting mixture is poured into water, extracted with ether and the ether extracts washed with water.The ether is evaporated off to yield an oil which is purified on a silica-gel column employing n-hexane/ethylacetate (24:1) as eluant to yield the title compound in the form of an oil. nod25 1.5312.
Example 3 1- {3, 4 - dichlorophenoxy) -2- methyl 4- [{ a a - trifluoro - m - tolyl) oxy] - butane Process b) 20 ml of ethyl acetate and 3.0 g (0.00767 M) of 1 (3,4 - dichlorophenoxy) - 2 - methyl - 4 - [a, a, a - trifluoro - m - tolyl) oxy] - 2 - butene (mixed with it 3-methyl isomer, both mostly in trans form) are added to a hydrogenation flask containing a catalytic amount of palladium charcoal. Hydrogen is introduced stirring the mixture until no further hydrogen uptake is observed. The excess hydrogen is removed by suction and nitrogen introduced.The flask is opened, the catalyst filtered off and the solvent evaporated off to yield a colourless oil which on chromatography on a silica-gel column using n-hexane/ethyl acetate (98.5:1.5) as eluant gives the title compound in admixture with a lesser portion of its 3-methyl isomer, nD20 1.5312.
Example 4 1,4-bis-[foe, 0!, - trifluoro-m-tolyl) oxy] - 2,3 - epoxy butane - Process a) Asolution of7.4 g (0.0196 M) of 1, 1' -[(2 - butene - 1,4-diyl)-bis-(oxy)] bis-3trifluoromethylbenzene in 20 ml of methylene chloride is added at room temperature to 4 g of m-chloro-perbenzoic acid in 50 ml of methylene chloride. The mixture is stirred for four days when a precipitate forms and then poured into 100 ml of saturated aqueous sodium sulphite. The product is extracted with ether, the ethereal extract washed twice with saturated aqueous sodium carbonate and once with saturated aqueous sodium chloride. The ether extract is dried over anhydrous sodium sul phate and the ether subsequently evaporated off.
The resulting oil is purified on a silica-gel column employing chloroform as eluant. The title product is obtained as a colourless oil.
Example 5 In analogous manner to that described in the preceding Examples 1 and 2, the following indicated compounds are produced either in substantially pure form or as the major component of a product mixture with a position isomer that is indicated in parenthesis. Where geometrical isomerism is possible, the essentially sole or predominant geometrical form is depicted in the formulae, except to the extent otherwise noted.
Z40 Title compound of Example 3 together with its 3-methyl isomer(nJ0 = 1.5312) Z41 title compound of Example4 Oil Example 6 In analogous manner to that described in the preceding Example 3 and using the corresponding 2-butene compound as starting material the compound as defined in Example 5Z21 is obtained.
Example 7 In analogous manner to that described in the preceding Example 4 and using the corresponding 2-butene compounds as starting material, the following compounds are obtained: compound as defined in the Examples 5i and 5Z30.
ExampleS 7-bromo-2-ethyl-4-(m- trifluoromethylphenoxy) - butene - 2 (and3-ethyl isomer)
To a flask charged with 7.26 g of 1,4- dibromo - 2 ethylbutene - 2 and 10 ml of water and heated to 50"C, is added slowly over the course of 10 minutes a solution of 4.86 g of m-trifluoromethylphenol and 2.3 g of sodium hydroxide in 12 ml of water. The resulting mixture is heated at 80"C for 6 hours and the resulting organic phase extracted twice with chloroform, and the combined extracts washed with water.After filtering over Celite and silica gel, the chloroform system is evaporated in vacuo to an oil constituting an 86:14 mixture of the isomers 1 bromo - 2 - ethyl - 4 - (m - trifluoromethylphenoxy) butene - 2 and 1 - bromo - 3 - ethyl -4 -(m - trifluoromethylphenoxy) - butene - 2, each of the position isomers having acis:trans ratio of 20:80.
Example 9 The isomeric mixture obtained in Example 8 is subjected to gas chromatography to separate and obtain the individual isomers in substantially pure form without variation oftheircis:trans ratio. The 1 bromo - 2 - ethyl - 4 - (m - tri - fluoromethylphenoxy) butene - 2 is then reacted with 3 4, - dichlorophenol analogously to Example 2 to obtain 1 - (3,4 - dichlorophenoxy) - 2-ethyl - 4 - [a, a, a - trifluoro - m - tolyl) oxy] - 2 - butene (similarcis:trans ratio) which is then hydrogenated analogousiy to Example 3 to obtain substantially pure 1 - (3,4 - dichlorophenoxy) -2-ethyl-4-[a,a,a-trifluoro-m-tolyl) oxy] butene.

Claims (78)

1. A process for the production of a compound of formula I.
wherein X and X' are independently H, fluoro, chloro, bromo, CF3, Cl-C4alkyl, C1-C4alkoxy, C,-C4alkylthio, nitro, cyano, amino, mono C1-C4alkylamino, di-C1-C4alkylamino, C1-C4alkylsulphonyl or C1-C4alkylsulphinyl, or X is as above defined and X' is phenoxy or phenoxy mono- or di- substituted by fluoro, chloro, bromo, CF3, C1-C4alkyl or C1-C4alkoxy, Y and Y' are independently H, fluoro, chloro, bromo, CF3, C1-C4alkyl, C1-C4alkoxy, C1-C4alkylthio or nitro, or X and Y and/or X' and Y' together form C1-C2alkylenedioxy on adjacent ring carbon atoms Z is H,fluoro, chloro, bromo,CF3 or C1-C4alkyl, R and Rs are independently H, C1-C4alkyl or -COOR8 wherein R3 is H or C1-C4alkyI, R1 and R3 are independently H, C1-Csalkyl, fluoro, chloro, bromo or hydroxy, and R3 and R4 are independently H or C1-C3alkyl or both together form a covalent bond or an epoxy bridge (-O-), with the proviso that no two adjacent ring substituents in either rings a orp are from the group of t-butyl, t-butoxy and CF3, which comprises a) condensing a compound of the formuia II and/or
wherein X, Y, X', Y' and Z are as above defined, with an aliphatic hydrocarbon derivative of the formula Ill,
wherein R, R1, R2, R3, R4 and R5 are as above defined and 0 is a leaving group displaceable under phenolic hydroxy condensing conditions, and 0' is either) a leaving group displaceable under phenolic hydroxy condensing conditions or ii) a radical of the formula B or B',
wherein X, Y, X', Y' and Z are as above defined, with the proviso that at least one of the reactants II, II' or Ill contains the B' radical, b) in order to prepare compounds of formula I in which R2 and R4 are both H reducing the double bound in the 2-butene group of a compound of the formula 1',
wherein X, Y, X', Y', Z, R, R1, R3 and R5 are as above defined, with an alkene reducing system or c) in order to prepare compounds of the formula I".
wherein X, Y, X', Y', R, R1, R3 and R5 are as above defined, epoxylating the double bound in the butene group of a compound of the formula 1', above stated.
2. A process for the production of a compound of formula I substantially as hereinbefore described with reference to any one of the Examples.
3. A compound of formula I whenever produced by a process according to Claim 1 or 2.
4. A compound offormula I as defined in Claim 1.
5. A compound of Claim 4, wherein the depicted CF3 group is attached to the 3-position of Ring a.
6. A compound of Claim 5, wherein one of R1 and R3 is H and the other H or C1-C4alkyl.
7. A compound of Claim 6, wherein R1 is methyl or ethyl.
8. A compound of Claim 6, of the formula
wherein X is H, fluoro, chloro, bromo, CF3, nitro and C1-C3alkyl, Y is H, fluoro, chloro, bromo and CF3 one of R1 and R3 is H or C1-C4alkyl and the other H, and R2 and R40 are either both H or together form a covalent bond.
9. A compound of Claim 8, wherein R20 and R4, are both H.
10. The compound of Claim 5, wherein X, Y, R, R1, R3, R5, Y' and Z are each H, R2 and RA form together a covalent bond and X' is 3-CF3.
11. The compound of Claim 5, wherein X, Y, R, R8, Y' and Z are each H, R1 and R3 are both CH3, R2 and R4 form together a covalent bond and X' is 3-CF3.
12. The compound of Claim 5, wherein X, Y, R, R1, R8, Y' and Z are each H, R2 and R4 form together a covalent bond, R3 is CH3 and X' is 3-CF3.
13. The compound of Claim 5, wherein X, Y, R, R8, Y' and Z are each H, R3 and R4 form together a covalent bond, R3 is C3H8 and X' is 3-CF3.
14. The compound of Claim 5, wherein X, Y, R, R1, R3, R5 and Z are each H, R2 and R4 form together a covalent bond, X' is 2-CI and Y' is 4-CI.
15. The compound of Claim 5, wherein X, Y, R, R1, R8 and Z are each H, R3 is C2Hs, R2 and R4 form together a covalent bond, X' is 3-CI and Y' is 4-CI.
16. The compound of Claim 5, wherein X, Y, R, R1, R5 and Z are each H, R3 is CH3, R3 and R4 form together a covalent bond, X' is 3-CI and Y, is 4-CI.
17. The compound of Claim 5, wherein X, Y, R, R1, R3, R5 and Z are each H, R2 and R4 form together a covalent bond, X' is 3-CI and Y' is 5-CI.
18. The compound of Claim 5, wherein X, Y, R, R2, RA, Rs, Y' and Z are each H, R1 is Br, R3 is OH and X' is 3-CF3.
18a. The compound of Claim 5, wherein X, Y, R, R1, R3, RA, R3, R5, Y' and Z are each H and X' is 3-CF3.
19. The compound of Claim 5, wherein X, Y, R1, R2, R4, R3, R8, Y' and Z are each H, R is CH3 and X' is 3-CF3.
20. The compound of Claim 5, wherein X, Y, R1, R2, R4, R3, R5, Y' and Z are each H, R is CO2CH3 and X' is 3-CF3.
21. The compound of Claim 5, wherein X, Y, R, R1, R2, R4, R3, R8 and Z are each H, Xis 3-CF3 and Y' 5-CF3.
22. The compound of Claim 5, wherein X, Y, R, R2, R4, R3, Y' and Z are each H, R1 is CH3, R3 is CH3 and X' is 3-CF3.
23. The compound of Claim 5, wherein X, Y, R, R3, R2, R4, Rsl Y' and Z are each H, R1 is CH3 and X' is 3-CF3.
24. The compound of Claim 5, wherein X, Y, R, R3, R3, R4, Rsl Y' and Z are each H, R1 is C2H5 and X' is 3-CF3.
25. The compound of Claim 5, wherein Y, R, R1, R3, R4, R3, R5 and Z are each H, X is 4-NO2, X' is 3-CF3 and Y' is 4-NO3.
26. The compound of Claim 5, wherein X, Y, R, R1, R2, R4, R3, R8 and Z are each H, X' is 2-CI and Y' is 4-CI.
27. The compound of Claim 5, wherein X, Y, R, R1, R2, R4, R3, R^l Y' and Z are each H and X' is 3-Cl.
28. The compound of Claim 5, wherein X, Y, R, R1, R3, R4, R3, R5, Y' and Z are each H and X' is 3-CH3.
29. The compound of Claim 5, wherein X, Y, R, R1, R2, R4, R3, R5, Y' and Z are each H and X' is 4-CI.
30. The compound of Claim 5, wherein X, Y, R, R1, R2, R4, R3, Rst X', Y' and Z are each H.
31. The compound of Claim 5, wherein X, Y, R, R1, R2, R4, R3, R5, Y' and Z are each H and X' is 3-OCH3.
32. The compound of Claim 5, wherein X, Y, R, R1, R2, R4, R3, R3, Y' and Z are each H and X' is 3-CN.
33. The compound of Claim 5, wherein X, Y, R, R1, R2, R4, R3, R8, Y' and Z are each H and X' is 3-i-C3H7.
34. The compound of Claim 5, wherein X, Y, R, R1, R2, R4, R3, R5 and Z are each H, X' is 3-CI and Y' is 5-OCH3.
35. The compound of Claim 5, wherein X, Y, R, R1, R2, R4, R3, R5, Y' and Z are each H and X' 4-SCH3.
36. The compound of Claim 5, wherein X, Y, R, R1, R2, R4, R3, R5, Y' and Z are each H and X' is 4-C3H5.
37. The compound of Claim 5, wherein X, Y, R, R, R2, R4, R3, R8, Y' and Z are each H and X' is 3-F.
38. The compound of Claim 5, wherein X, Y, R, R1, R2, R4, R3, R5 and Z are each H, X' is 3-CI and Y' is 5-CI.
39. The compound of Claim 5, wherein X, Y, R, R1, R2, R4, R3, R5 and Z are each H, X' is 2-CI and Y' is 4-CF3.
40. The compound of Claim 5, wherein X, Y, R, R1, R2, R4, R3, R8 and Z are each H, X' is 24-C4H8 andY' is 4-t-C4Hs.
41. The compound of Claim 5, wherein X, Y, R, R1, R2, R4, R3, R5, Y' and Z are each H and X' is 3-N(CH3)3.
42. The compound of Claim 5, wherein X, Y, R, R1, R2, R4, R3, Y' and Z are each H, R8 is CH3 and X' is 3-CH3.
43. The compound of Claim 5, wherein X, Y, R, R1, R2, R4, R3, Y, and Z are each H, R5 is CH3 and X' is 3-CI.
44. The compound of Claim 5, wherein X, Y, R, R, R2, R4, R3, R5 and Z are each H, X' is 3-CF3 and Y' is 4-NO2.
45. The compound of Claim 5, wherein X, Y, R, R1, R2, R4, R3, R5, Y' and Z are each H and X' is 3-p - CI - phenoxy.
46. The compound of Claim 5, wherein X, Y, R, R1, R2, R4, R3, R8 and Z are each H, X' is 2-NO2 and Y' is 4-CF3.
47. The compound of Claim 5, wherein X, Y, R, R1, R2, R4, R3, R8 and Z are each H, X' is 4-NH2 and Y' is 3-CF3.
48. The compound of Claim 5, wherein X, Y, R, R1, R2, R4, R3, R5 and Z are each H, X' is 4-NH2 and Y' is 2-CF3.
49. The compound of Claim 5, wherein X, Y, R, R3, R2, R4, R8 and Z are each H, R1 is C2Hs, X' is 3-CI and Y' is 4-CI.
50. The compound of Claim 5, wherein X, Y, R, R1, R2, R4, R3 and Z are each H, R8 is CH3, X' is 3-CI and Y' is 4-CI.
51. The compound of Claim 5, wherein X, Y, R, R1, R2, R4, R3, R8 and Z are each H, X' is 4-CF3 and Y' is 3-CI.
52. The compound of Claim 5, wherein X, Y, R, R1, R2, RA, R5, Y' and Z are each H, R3 is n-C3H, and X' is 3-CF3.
53. The compound of Claim 5, wherein X, Y, R, R2, R8, Y' and Z are each H, R. is Br, RA is C2Hs, R is OH and X' is 3-CF3.
54. The compound of Claim 5, wherein X, Y, R, R1, R2, RA, R3, R5 and Z are each H and X' andY' together form 3,4-methylenedioxy.
55. The compound of Claim 5, wherein X, Y, R, R2, R8, Y' and Z are each H, R1 and Rj are Br, RA is C,H5 and X' is 3-CF3.
56. The compound of Claim 5, wherein X, Y, R, R1, R2, RA, R3, R5, Y' and Z are each H and X' is 4-CH3SO2.
57. The compound of Claim 5, wherein X, Y, R, R1, R2, RA, R3, R5, Y' and Z are each H and X' is 3-CH3SO.
58. The compound of Claim 5, wherein X, Y, R, R1, R2, R4, R5 and Z are each H, R3 is C2Hs, X' is 2-NO2 and Y' is 4-CF3.
59. The compound of Claim 5, wherein X, Y, R, R1, R2, R4 and R8 are each H, R3 is C2Hs, X' is 2-NO2, Y' is 6-NO2 and Z is 4-CF3.
60. The compound of Claim 5, wherein X, Y, R, R1, R2, Rq, R3, Rs and Z are each H, X' is 2-NH2 and Y' is 4-CF3.
61. The compound of Claim 5, wherein X, Y, R, R1, R2, R5, Y' and Z are each H, R4 is OH, R3 is C3H5 and X' is 3-CF3.
62. The compound of Claim 5, wherein X, Y, R, Rl, R2, RA, R3 and R5 are each H, X' is 2-CH3, Y' is 6-CH3 and Z is 4-Br.
63. The compound of Claim 5, wherein X, Y, R, R1, R2, R8 and Z are each H, R4 is CH3, R3 is CH3, X' is 3-CI and Y' is 4-CI.
64. The compound of Claim 5, wherein X, Y, R, Rl, R2, R4, R5, Y' and Z are each H, R3 is C2H5 and X' is 4-CI.
65. The compound of Claim 5, wherein X, Y, R, R1, R2, R5, Y' and Z are each H, RA and R3 are CH3 and X' is 2-CF3.
66. The compound of Claim 5, wherein X, Y, R, R2, R4, R3, R5 and Z are each H, R1 is C2Hs, X' is 3-Cl and Y' is 4-CI.
67. The compound of Claim 5, wherein X, Y, R, R1, R2, R4, R5 and Z are each H, R3 is CH3, X' is 3-CI and Y' is 4-CI.
68. A method of combating weeds, comprising applying to a weed locus a herbicidally effective amount of a compound of Claim 4.
69. A method of selectively combating weeds in a crop locus, which comprises applying to said locus 0.1 to 7.0 kg per hectare of a compound claimed in any one of Claims 3 to 67.
70. A method according to Claim 69, in which the crop locus is selected from the group consisting of wheat, corn and carrots.
71. A method according to any one of Claims 69 and 70 wherein the compound is applied post emergence the weeds.
72. A method according to Claim 71 wherein the compound is applied post emergence both the weeds and the crop.
73. An agrocultural composition comprising an inert herbicide carrier and a herbicidally effective amount of a compound claimed in any one of Claims 3to67.
74. A herbicidal composition according to Claim 73 containing between 0.01 and 10% by weight of a compound claimed in any one of claims 3 to 67.
75. A herbicidal composition concentrate comprising between 2% and 8% by weight of a compound claimed in any one of Claims 3 to 67.
76. The compound of Claim 5, wherein X, Y, R, R1, R2, Ra, R4, R5, Y' and Z are each H and X' is 2-CF3.
77. The compound of Claim 5, wherein X, Y, R, R1, R2, R3, R4, Rs and Z are each H, X' is 3-CI and Y' is 4-CI.
Example Z42
78. The compound of Claim 5, wherein X, Y, R, R2, R3, R4, Rsl and Z are each H, X' is 2-NO2, Y' is 4-CF3 and R1 is C2Hs.
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