GB2142629A

GB2142629A - Herbicidal 2,3-dihydrofuran derivatives

Info

Publication number: GB2142629A
Application number: GB08415480A
Authority: GB
Inventors: Carl E Ward
Original assignee: Chevron Research and Technology Co; Chevron Research Co
Current assignee: Chevron USA Inc
Priority date: 1983-06-17
Filing date: 1984-06-18
Publication date: 1985-01-23
Also published as: IL71981A; ES544952A0; MX7700E; ES8604187A1; KR910005893B1; IT8421432A1; NL193833B; IL71981A0; DE3422346C2; ATA192984A; DE3422346A1; ES533473A0; ES8604916A1; IT8421432A0; ES544953A0; ES544951A0; GB8415480D0; ES544949A0; CH659651A5; GB2142629B

Abstract

5-Amino-3-oxo-4-(substituted-phenyl)-2,3-dihydrofuran and derivatives thereof generally exhibit both pre-emergence and post-emergence phytotoxicity and are useful as herbicides and also at low dosages as plant growth regulating agents.

Description

SPECIFICATION Herbicidal 2,3-dihydrofuran derivatives This invention relates to 5-am ino-3-oxo-4-(substituted-phenyl)-2,3-dihydrofuran derivatives and to the use of such compounds as herbicides and plant growth regulators.

Chemiker-Zeitung 104(1980) No. 10, Pages 302-303, is an academic paper disclosing the ring closure of 1 -(dimethylamino)-2,4-diphenyl-1 -buten-3,4-dione to yield 5-dimethylamino-2,4-diphenyl-2,3-dihydrofuran.

British Patent No. 1,521,092, discloses certain 3-phenyl-5-substituted-4(iH)-pyrid-ones or-thiones as herbicides. Japanese Patent Application 13,710/69 (Chemical Abstracts 71 :61195e) discloses the generic formula for 5-amino-3-oxo-4-(phenyl and halophenyl)-2,3-dihydrofuran and specificaily discloses 5-amino-3oxo-4-(phenyl and 4-chlorophenyl)-2,3-dihydrofurans. Japanese Patent No. 19090 (Chemical Abstracts 69P10352e) discloses certain 2,3-dihydrothiophenes as pharmaceuticals. Helvetica ChemicaActa, Volume 66, Pages 362-378 (1983) discloses 5-N-cyclopropyl-4-phenyl-2-methoxycarbonyl-methylene-3-furanone as part of an academic chemical synthesis discussion. U.S.Patent No. 4,441,910 discloses herbicidal ureidosulfonylfurans and ureidosulfonylthiophenes.

The present invention provides compounds having both pre-emergence and post-emergence herbicidal activity and having especially good pre-emergence activity against a broad spectrum of both broad-leaf weeds and grassy weeds. At lower application rates the compounds also exhibit plant growth regulating properties.

The compounds of the present invention can be represented by the following general formula:

wherein R is lower alkyl having 1 to 4 carbon atoms; cycloalkyl having 3 to 7 carbon atoms; lower alkenyl; haloalkyl having 1 to 4 carbon atoms and 1 to 3 halo atoms independently selected from fluoro, chloro, bromo and iodo; haloalkenyl having 2 to 4 carbon atoms and 1 to 3 halo atoms independently selected from fluoro, chloro, bromo and iodo; lower alkoxy; lower alkylthio; lower alkoxyalkyl wherein the alkoxy and alkyl moiety thereof independently have 1 to 3 carbon atoms; lower alkylthioalkyl wherein the alkyl moieties independently have 1 to 3 carbon atoms; phenyl, naphth-1-yl, inden-1-yl; 4-fluorophenyl; arylalkylene having 1 to 3 carbon atoms in the alkylene moiety and wherein said aryl moiety is phenyl, naphth-1-yl or inden-1 -yl; or substituted aryl or arylalkylene selected from:

wherein one, two or three of R4, R5, R6, R7, R8, and R9 are independently selected from lower alkyl, lower alkoxy, halo, nitro, or haloalkyl having 1 to 3 carbon atoms and 1 to 3 ofthe same or different halo atoms, and the remainder are hydrogen; and R3 is a single bond or an alkylene having 1 to 3 carbon atoms; R1 is a hydrogen or alkyl having 1 to 4 carbon atoms; R2 is hydrogen, alkyl having 1 to 4 carbon atoms, alkenyl having 3 to 4 carbon atoms, alkoxycarbonylalkyl having from 1 to 4 carbon atoms in the alkoxy moiety and from 1 to 4 carbon atoms in the alkyl moiety, alkoxyalkyl wherein the alkoxy and alkyl moieties independently have 1 to 3 carbon atoms, or alkylthioalkyi wherein the alkyl moieties independently have 1 to 3 carbon atoms; or R1 and R2 together with the nitrogen to which they are joined form a saturated or unsaturated nitrogen heterocycle having from 3 to 6 ring atoms of which one is nitrogen and the remainder are carbon atoms; Xis hydrogen, lower alkyl, lower alkoxy, halo, or trifluoromethyl and can be at any available position on the phenyl ring; and Y is lower alkyl, lower alkoxy; halo; lower haloalkyl having 1 to 4 carbon atoms and 1 to 3 of the same or different halo atoms; lower haloalkoxy having 1 to 4 carbon atoms and 1 to 3 of the same or different halo atoms; or lower haloalkylthio having 1 to 4 carbon atoms and 1 to 3 of the same or different halo atoms; with the proviso that when Y is halo then R, R1 and R2 are not all hydrogen and the further proviso that when Y is other than trifluoromethyl and Xis other than hydrogen, and R1 is hydrogen and R2 is hydrogen, then R is methyl, ethyl, propyl, 2-halophenyl, 2-lower alkylphenyl or 4fluorophenyl.

The invention also comprises compatible salts of the compounds of Formula (I), for example salts obtained via replacement of the amino hydrogen (i.e., R' and R2 is hydrogen) with a compatible cation or enolation of the 3-oxo group following replacement of the amino hydrogen.

The compounds of Formula (I) exist as keto enol isomers. The compounds also have an asymmetric carbon atom and can also exist as optical isomers. In some instances the compounds also exist as geometric isomers. The above formula is intended to encompass the respective individual isomers as well as mixtures thereof and the respective isomers as well as mixtures thereof are encompassed within the invention.

It has also been discovered that the presence of a 3-trifluoromethyl substituent on the 4phenyl group of the compounds of the present invention generally very substantially enhances herbicidal activity.

In a further aspect the invention provides a herbicidal composition comprising a compatible carrier and a herbicidally effective amount of a compound of Formula (I), or a compatible salt thereof, or a mixture thereof.

The present invention also provides a method for preventing or controlling the growth of unwanted vegetation, which comprises treating the growth medium and/or the foliage of such vegetation with a herbicidally effective amount of the compound(s) of Formula (I) and/or compatible salts thereof.

In another aspect, the present invention provides a plant growth regulating composition comprising a compatible carrier and a plant growth regulating amount of a compound of Formula (I), a compatible salt of Formula (I), or a mixture thereof, effective to alter the normal growth pattern of said plants.

The present invention also provides a method for regulating plant growth which comprises treating the growth medium and/or the foliage of such vegetation with a plant growth regulating effective amount of the compound(s) of Formula (I) and/or compatible salts thereof, effective to alter the normal growth pattern of said plants.

The present invention also provides chemical intermediates and processes for preparing the compounds of Formula (I).

The invention will be further described hereinbelow.

Illustrations of typical compounds of Formula (I) of the present invention can be had by reference to Examples 2, 3 and 6-10 set forth hereinbelow. In terms of substituents, the preferred -- compounds are those wherein R is lower alkyl, aryl or substituted aryl, more preferably methyl, ethyl, propyl, phenyl or substituted phenyl, and especially phenyl, monomethylphenyl or monohalophenyl, more especially methyl, ethyl, n-propyl, 2-halophenyl, 2-lower alkylphenyl, or 44luorophenyl; R' and R2 are independently hydrogen, methyl, ethyl or n-propyl, and more preferably one of R1 or R2 is hydrogen and the other is hydrogen, methyl, ethyl or n-propyl, preferably hydrogen, methyl or ethyl, especially methyl;; Xis hydrogen and/orY is 3-trifluoromethyl or 3-halo, especially 3-trifluoromethyl. Most preferably the compounds contain a combination of two or more preferred substituents.

The compounds of Formula (I) wherein F1 and R2 are each hydrogen and R is aryl or substituted aryl can be conveniently prepared by the following schematically represented process:

wherein X and Y are as defined hereinabove; and Z' is aryl or substituted aryl.

Rearrangement of Compound (A) to Compound (I') can be conveniently effected by contacting Compound (A) with a halogen, preferably bromine, and a liquid carboxylic acid in the presence of an inert organic solvent.

Typically, this process is conducted at temperatures in the range of from 0 to 100"C, preferably from 20 to 30"C, for from 4 to 36 hours, ------ preferably from 18 to 24 hours, using from 1.0 to 10.0, preferably 1.0 to 1.1. moles of halogen per mole of Compound (A). Suitable liquid carboxylic acids which can be used include, for example, acetic acid, propionic acid, butyric acid and formic acid. By using excess carboxylic acid, the excess can serve as solvent or liquid carrier for this reaction system.Other organic solvents which can be used include, for example, liquid halogenated alkanes, for example, methylene chloride, carbon tetrachloride, chloroform, 1,2-dichloroethane; liquid aromatics, for example, benzene, toluene; liquid alkyl ethers, for example, diethylether, dimethyl, sulfoxide, dimethylforamide, and compatible mixtures thereof.

Best results are obtained using bromine as the halogen, although chlorine and iodine could also be used.

The starting materials of Formula (A) can be prepared by the following schematically represented process:

wherein R1 is lower alkyl, aryl (e.g. phenyl) or arylalkylene (e.g. benzyl); and Z', Y and X are as defined hereinabove.

This process can be conveniently effected by contacting Compound (B) with Compound (C), and a strong base, preferably in an inert organic solvent.

Typically, this process is conducted at temperatures in the range of from 0" to 100 C, preferably 75 to 850C, for from 5 to 36 hours, preferably 18 to 24 hours, using from 1.0 to 10.0, preferably 1.0 to 1.2 moles of Compound (C) per mole of Compound (B). Typically, from 1.0 to 10.0 moles of base are used per mole of Compound (C).

Suitable strong bases which can be used include, for example, alkali metal alkanolates, for example, sodium methoxide, sodium ethoxide, potassium ethoxide, sodium hydride and potassium hydride. The strong base should preferably be one which does not yield water as a by-product in this reaction system.

Suitable inert solvents which can be used include, for example, lower alkanols (for example, methanol, ethanol, and propanol) tetrahydrofuran, dimethoxyethane, dioxane, and compatible mixtures thereof.

Conveniently, the alkali metal alkanolate is prepared in situ by reacting an alkali metal with excess alkanol which in turn serves as solventforthe above reaction.

The starting materials of Formulas (B) and (C) are generally known materials and can be prepared by known procedures, or obvious modifications thereof (i.e., substitution of appropriate starting materials). The preparation of Compound (B) is for example described in Org. Syn. Coll., Volume 1, 107(1941), and the preparation of Compound (C) is described in Org. Syn. Coll., Volume 1,270 (1941).

The compounds of Formula (I) wherein R1 and R2 are each hydrogen can be prepared via the general process schematically represented by the following overall reaction equation:

wherein R, and X and Y are as defined hereinabove; and R5 is lower alkyl, aryl (e.g. phenyl) or arylalkylene (e.g. benzyl).

This process can be conveniently effected by contacting Compound (B) with Compound (E), and a strong base (e.g. sodium methoxide, sodium ethoxide), preferably in an inert organic solvent.

Typically, this process is conducted at temperatures in the range of from 0 to 100"C, preferably 75 to 85"C for from 5 to 36 hours, preferably 18 to 24 hours, using from 1.0 to 10.0, preferably 1.0 to 1.2 moles of Compound (E) per mole of Compound (B). Suitable inert organic solvents which can be used include, for example, lower alkanols (e.g. methanol, ethanol, propanol, etc.); tetrahydrofuran; dimethoxyethane; dioxane; and compatible mixtures thereof.

Suitable bases which can be used for this process include those bases previously described with respect to the reaction of Compound (B) with Compound (C).

The hydroxy esters of Formula (E) are generally known compounds and can be prepared by known procedures or by obvious modifications thereof (e.g., by using appropriately substituted starting materials).

The compounds of Formula I wherein R1 and R2 are hydrogen and R is alkyl, cycloalkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, arylalkylene, substituted arylalkylene or alkenylalkyl (e.g., -CH2CH=CH) can also be conveniently prepared by the following schematically represented process:

wherein R"' is alkyl, cycloalkyl, alkoxyalkyl, alkoxy, alkylthioalkyl, arylalkylene, substituted arylalkylene or alkenyl and R10 is lower alkyl, preferably methyl.

This process can be conveniently effected by contacting Compound (A') with a cyclizing agent, under reactive conditions, preferably in an inert organic solvent.

Typically,this process is conducted attemperatures in the range of from Oto200 C, preferablyfrom 115to 120"C, for from 10 to 120 minutes, preferably from 10 to 30 minutes, using from 1 to 10, preferably 1 to 2, moles of cyclizing agent per mole of Compound (A'). Suitable cyclizing agents which can be used include, for example, strong anhydrous acids, for example, sulfuric acid, hydrogen chloride, hydrogen bromide, trifluoroacetic acid and methane sulfonic acid. Best results are typically obtained using anhydrous sulfuric acid. Suitable inert organic solvents which can be used include, for example, acetic acid, propionic acid, butyric acid, toluene, xylene, and compatible mixtures thereof.

The starting materials of Formula (A') can be prepared via the following schematically represented process:

wherein Rand R10 are as defined hereinabove; X' is chloro, bromo or iodo and M and M' are independently sodium or lithium.

Although this process is schematically shown as three steps, the steps are typically and conveniently conducted in situ. Also as is conventional with such reactions the reactions are preferably conducted under substantially anhydrous condition under an inert gas (e.g., nitrogen).

In the first step of this process compound (B') is contacted with a non-nucleophilic base, preferably in an inert organic solvent. This step is typically conducted at temperatures in the range of from 0-25"C for from 1/2 to 3 hours using from 1 to 2, preferably 1 to 1.3, mole equivalents of non-nucleophilic base per mole of compound (B'). Suitable non-nucleophilic bases which can be used include, for example, alkali metal hydrides, e.g., sodium hydride, potassium hydride, etc.; alkali metal amides, e.g., lithium bis(trimethylsilyl)amide; sodium bis(trimethylsilyl)amide; potassium bis(trimethylsilyl)amide; lithium diethylamide, lithium diisopropyl amide; and sodium dimethylamide. Sodium hydride is generally preferred as it has given very good results and is readily commercially available. The alkali metal amides, and also of course the alkali metal hydrides, are generally known compounds and can be prepared by known procedures, or obvious modifications thereof. For example, the alkali metal amides can be prepared by the reaction of a secondary amine with an alkyl alkali metal.

Suitable inert organic solvents, which can be used, include, for example, tetrahydrofuran, dioxane, dimethoxyethane, diethyl ether, diisopropyl ether, and compatible mixtures thereof.

The second step can be effected by contacting compound (B") with an alkyl base preferably in an inert organic solvent. As before noted, this process step is preferably conducted in situ with the reaction product mixture of the first step. Typically the second step is conducted at temperature ranges of from -78 to 0 C forfrom 1 to 4 hours using from 1 to 2, preferably 1 to 1.3 mole equivalents of alkyl base per mole of compound (B"). Suitable alkyl bases which can be used include for example alkyl-alkali metals and alkyl Grignard reagents. Preferably n-butyl-lithium is used as it gives good results and is readily commercially available. Suitable solvents which can be used include those listed above with respect to the first step and the like.

The third step can be effected by contacting compound (B"') with the appropriate R"' halide having the desired R"' group, preferably in an inert organic solvent. The third step is also typically conducted in situ with the reaction product mixture of the second step.

The third step of this process is typically conducted at temperatures in the range of from -30 to 30"C, preferably 22 to 25 "C for from 1 to 18 hours, preferably 1 to 5 hours using from 1 to 10 moles, preferably 1 to 1.5 moles of R"'X' per mole of B'D. Suitable inert organic solvents include those given above with respect to the first step of this process, and the like. The R"'X' halides are generally known compounds and can be prepared by known procedures or obvious modifications thereof (e.g., substitution of appropriate reactants and solvents).

The starting materials of Formula (B') can be prepared by the following schematically represented process:

wherein R1' is lower alkyl (preferably methyl) and R'O, Y and X are as defined hereinabove.

This process can be conveniently effected by contacting Compound (B) with Compound (C'), and a strong base under reactive conditions, preferably in an inert organic solvent.

Typically, this process is conducted using the same conditions as described hereinabove with respect to the preparation of Compound (A) save that reactant C' is used in place of reactant C. The reactants of Formula C' are simple alkyl alkoxyacetate esters, for example, methyl methoxyacetate. The preparation of such compounds is well known to the art.

The compound of Formula (I) wherein one or both of Rq and R2 are substituted can be prepared by alkylation of the amino group of the corresponding compounds for formula I":

wherein R, R1, X and Y are as defined hereinabove; and R2 is as defined for R2 but is not hydrogen; and F2,Z" is an alkylation agent having the appropriate R2 or appropriate R1 group if dialkylation is desired.

This process can be effected by contacting, Compound (I") with a suitable alkylation agent capable of alkylating primary or secondary amino groups.

For example, this can be effected by contacting Compound (I") with R2 iodide or bromide, preferably in an inert organic solvent and preferably in the presence of a scavenger base. Typically, this process is conducted at temperatures in the range of from 0" to 1 00'C, preferably 20 to 45"C for from 1.0 to 72.0, preferably 2.0 to 18.0 hours. Where it is desired to monoalkylate, then typically about from 1.0 to 1.1. moles of R2 halide reactant is used per mole of Compound (I"). Where it is desired to alkylate both amino hydrogens, then typically about from 1.9 to 4.0 moles of R2 halide are used per mole of Compound (I").In the case where it is desired to prepare the compound wherein R2 is alkoxyalkyl or alkylthioalkyl, it is preferred to use a large excess of R2 halide even where monoalkylation is desired; for example 3 to 6 moles of F2,Z" per mole of 1".

Further alkylation can be effected in a second step is desired. Also variation in R1 and R2 can be effected by first alkylating only one of the two amino hydrogens and then alkylating the second amino hydrogen with an alkylating agent having a different R2 group. The compounds wherein R1 and R2 together with the amino nitrogen atoms form a saturated heterocycle can be prepared by using the appropriate Z"-(CH2)2~5-Z", wherein Z" is Cl or Br alkylating agent. The R1R2N unsaturated heterocycle can be prepared by using the appropriate cis-alkenyl dihalide, wherein one of the halo atoms is on each of the terminal alkenyl carbon.

Suitable inert organic solvents which can be used, include, for example, liquid halogenated alkanes; for example, methylene chloride, carbon tetrachloride, or dichloroethane; also useful are tetrahydrofuran and the like. Suitable scavenger bases which can be used include, for example, the bases described hereinabove with respect to the reaction of Compound (B) with Compound (C).

The compounds of Formuia (I"') wherein R1 is lower alkyl (e.g. methyl) and R2 is hydrogen or lower alkyl, are advantageously prepared using dialkyl sulfate as the alkylating agent. This can be conveniently effected by contacting the compound of Formula I wherein one or both of R1 and/or R2 are hydrogen with the desired lower alkyl sulfate in the presence of a strong base and preferably in an inert organic solvent in the presence of a phase transfer agent. Typically, this process is conducted at temperatures in the range of from 0 to 100"C, preferably 20 to 45"C, using from 1.0 to 4.0 moles of dialkyl sulfate per mole of Compound I. An excess, typcially about 2.5 mole of base is used.Preferably, this process is also conducted in an inert organic solvent such as, for example, methylene chloride, carbon tetrachloride, dichloroethane, or tetrahydrofuran.

Suitable strong bases which can be used include, for example, sodium hydroxide, potassium hydroxide, sodium ethoxide, sodium carbonate and potassium carbonate.

Suitable phase transfer agents are agents which transfer hydrophilic ions into a lipophilic organic medium and include, for example, benzyl triethylammonium chloride, tetra-n-butylammonium chloride and methyltrioctylammonium chloride.

The compatible salts of Formula (I) can be prepared by conventional procedures for example by treating the compound of Formula (I) wherein F1 and/or R2 are hydrogen with a suitable strong base such as, for example, n-butyllithium, sodium hydride, potassium hydride, having the desired cation, by conventional procedures to yield the corresponding R1 and/or R2 cation salts. The enolate salts can be prepared by treating the R1 and/or R2 cation salts with base via conventional procedures. Additional variations in the salt cation can also be effected via ion exchange with an ion exchange resin having the desired cation.

Generalprocess conditions In the above-described processes, it is generally preferable to separate the respective products before proceeding with the next step in the reaction sequence, except where described as an in situ step or unless otherwise expressly stated. These products can be recovered from their respective reaction product mixtures by any suitable separation and purification procedure, such as, for example, recrystallization and chromatography. Suitable separation and purification procedures are, for example, illustrated in the Examples set forth hereinbelow.

Generally, the reactions described above are conducted as liquid phase reaction and hence pressure is generally not significant except as it affects temperature (boiling point) where reactions are conducted at reflux. Therefore, these reactions are generally conducted at pressures of from 300 to 3,000 mm of mercury and conveniently are conducted at about atmospheric or ambient pressure.

It should also be appreciated that where typcial or preferred process conditions (e.g., reaction temperatures, times, mole ratios of reactants, solvents, etc.) have been given, that other process conditions could also be used. Optimum reaction conditions (e.g., temperature, reaction time, mol ratios, solvents, etc.) may vary with the particular reagents or organic solvents used but can be determined by routine optimization procedures.

Where optical isomer mixtures are obtained, the respective optical isomers can be obtained by conventional resolution procedures. Geometric isomers can be separated by conventional separation procedures which depend upon differences in physical properties between the geometric isomers.

Definitions As used herein the following terms have the following meanings unless expressly stated to the contrary: The term "lower alkyl" refers to both straight- and branched-chain alkyl groups having a total of from 1 to 4 carbon atoms and includes primary, secondary and tertiary alkyl groups. Typical lower alkyls include, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, and t-butyl.

The term "alkylene" refers to both straight chained and branched chained alkylene groups and includes, for example,

The term "lower alkenyl" refers to alkenyl groups having 2 through 6, preferably 2 through 4, carbon atoms and includes, for example, vinyl, 1 -propenyl, 2-propenyl, 1 -methylvinyl, 1 -butenyl and 2-methyl prop- 1 -enyl.

The term "lower alkoxy" refers to the group -OR' wherein R' is lower alkyl.

The term "lower alkylthio" refers to the group -SR' wherein R' is lower alkyl.

The term "lower alkoxyalkyl" refers to the group R'OR"- wherein R' and R" are independently straight chain or branched chain alkyl groups having 1 to 3 carbon atoms.

The term "lower alkylthioalkyl" refers to the group R'SR"- wherein R' and R" are independently straight chain or branched chain alkyl groups having 1 to 3 carbon atoms.

The term "lower alkoxycarbonylalkyl" refers to the group

wherein R' is lower alkyl and R" is alkylene having 1 through 4 carbon atoms and can be straight or branched chained. Typical alkoxycarbonylalkyl groups include for example, -CH2C(O)OCHa; and -CH(CH3)C(O)OC2HS.

The term "halo" refers to the group offluoro, chloro, bromo and iodo.

The term "lower haloalkyl" refers to haloalkyl compounds having 1 to 4 carbon atoms and 1 to 3 halo atoms independently selected from the group of fluoro, chloro, bromo and iodo. Preferably the lower haloalkyl group has 1 or 2 carbon atoms.

The term "lower haloalkoxy" refers to "lower alkoxy" groups having 1 to 3 halo atoms independently selected from the group of fluoro, chloro, bromo or iodo.

The term "aryl" refers to aryl groups having 6 to 10 carbon atoms and includes, for example, phenyl, naphthyl and indenyl. Typically the aryl group will be phenyl or naphthyl as compounds having such groups are more readily available commercially than other aryl compounds.

The term "substituted aryl" refers to aryl groups having 1 to 2 substituents independently selected from the group of lower alkyl, lower alkoxy, halonitro, or haloalkyl having 1 to 3 carbon atoms and 1 to 3 halo atoms. Typical substituted aryl groups include, for example, 24luorophenyl, 2-chlorophenyl, 2,6- dimethylphenyl, 4-fluorophenyl, 2-methylphenyl, 2-chloro,3-chloromethylphenyl, 2-nitro,5-methylphenyl, 2,6-dichlorophenyl,3-trifluoromethylphenyl,2-methoxyphenyl,2-bromonaphth-1-yl and 3-methoxyinden-1 - yl.

The term "arylalkylene" refers to the group ArR3- wherein Ar is aryl and R3 is alkylene having 1 to 3 carbon atoms and includes both straight-chained and branched-chained alkylenes, for example, methylene, ethyl, 1-methylethyl, and propyl.

The term "(substituted aryl)alkylene" or "ring-substituted arylalkylene" refers to the group Ar'R3wherein Ar' is substituted aryl and R3 is alkylene as defined with respect to arylalkylene.

The term "saturated nitrogen heterocycle" as used herein with respect to F1 and R2 of formula I refers to the groups having the formula:

wherein n is 1,2, or 3.

The term "unsaturated nitrogen heterocycle" as used herein with respect to R1 and R2 of formula I refer to the groups having the formulas:

The term "compatible salts" refers to salts which do not significantly alter the herbicidal properties of the parent compound. Suitable salts include cation salts such as, for example, the cation salts of lithium, sodium, potassium, alkali earth metals, ammonia and quaternary ammonium salts.

The term "room temperature" or "ambient temperature" refers to 20-25"C.

Utility The compounds of Formula (I) exhibit both pre-emergence and post-emergence herbicidal activity and exhibit especially good pre-emergence herbicidal activity.

Generally, for post-emergent applications, the herbicidal compounds are applied directly to the foliage or other plant parts. For pre-emergence applications, the herbicidal compounds are applied to the growth medium, or prospective growth medium, for the plant. The optimum amount of the herbicidal compound or composition will vary with the particular plant species, and the extent of plant growth, if any, and the particular part of the plant which is contacted and the extent of contact. The optimum dosage can also vary with the general location or environment (e.g., sheltered areas such as greenhouses compared to exposed areas such as fields), and type and degree of control desired. Generally, for both pre- and post-emergent control, the present compounds are applied at rates of from 0.02 to 60 kg/ha, preferably from 0.02 to 10 kg/ha.

Also, although in theory the compounds can be applied undiluted, in actual practice they are generally applied as a composition or formulation comprising an effective amount of the compound(s) and an acceptable carrier. An acceptable or compatible carrier (agriculturally acceptable carrier) is one which does not significantly adversely affect the desired biological effect achieved by the active compounds, save to dilute it. Typically, the composition contains from 0.05 to 95% by weight of the compound of Formula (I) or mixtures thereof. Concentrates can also be made having high concentrations designed for dilution prior to application. The carrier can be a solid, liquid, or aerosol. The actual compositions can take the form of granules, powders, dusts, solutions, emulsions, slurries, aerosols, and the like.

Suitable solid carriers which can be used include, for example, natural clays (such as kaolin, attapulgite, montmorillonite, etc.), talcs, pyrophyllite, diatomaceous silica, synthetic fine silica, calcium aluminosilicate, tricalcium phosphate, and the like. Also, organic materials, such as, for example, walnut shell flour, cotton-seed hulls, wheat flour, wood flour, and wood bark flour, can also be used as carriers. Suitable liquid diluents which can be used include, for example, water and organic solvents (e.g., hydrocarbons such as benzene, toluene, dimethylsulfoxide, kerosene, diesel fuel, fuel oil and petroleum naphtha). Suitable aerosol carriers which can be used include conventional aerosol carriers such as halogenated alkanes.

The composition can also contain various promoters and surface-active agents which enhance the rate of transport of the active compound into the plant tissue such as, for example, organic solvents, wetting agents and oils, and in the case of compositions designed for pre-emergence application agents which reduce the leachability of the compound or otherwise enhance soil stability.

The composition can also contain various compatible adjuvants, stabilizers, conditioners, insecticides, fungicides, and if desired, other herbicidally active compounds.

At reduced dosages the compounds of the present invention also exhibit plant growth regulating activity and can be used to alter the normal growth pattern of green plants.

The compounds of Formula (I) can be applied as plant growth regulators in pure form, but more pragmatically, as in the case of herbicidal application, are applied in combination with a carrier. The same types of carriers as set forth hereinabove with respect to the herbicidal compositions can also be used.

Depending on the desired application, the plant growth regulating composition can also contain, or be applied in combination with other compatible ingredients such as desiccants, defoliants, surface-active agents, adjuvants, fungicides, and insecticides. Typically, the plant growth regulating composition will contain a total of from 0.005 to 90 wt. % of the compound(s) of Formula (I) depending on whether the composition is intended to be applied directly or diluted first.

A further understanding of the invention can be had from the following non-limiting Preparation and Examples. Wherein, unless expressly stated to the contrary, all temperatures and temperature ranges refer to the Centigrade system and the term "ambient" or "room temperature" refers to about 20-25"C. The term "percent" or "%" refers to weight percent and the term "mole" or "moles" refers to gram moles. The term "equivalent" refers to a quantity of reagent equal in moles, to the moles of the preceding or succeeding reactant recited in that example in terms of finite moles or finite weight or volume.Where given, proton-magnetic resonance spectrum (p.m.r. or n.m.r.) were determined at 60 mHz, signals are assigned as singlets (s), broad singlets (bs), doublets (d), double doublets (dd), triplets (t), double triplets (dt), quartets (q), and multiplets (m); and cps refers to cycles per second. Also where necessary examples are repeated to provide additional starting material for subsequent examples.

EXAMPLES Example 1 (3- Trifluorom ethylphen ylj-benzylcarb on yl-acetonitrile In this example, 4.91 g of metallic sodium was added to 110 ml of anhydrous ethanol at room temperature and stirred until all of the sodium dissolved. A mixture containing 18.76 g of (3-trifluoromethylphenyl) acetonitrile and 21.73 g of ethyl phenylacetate was then added dropwise and the resulting mixture was stirred at reflux for about 18 hours. The mixture was then poured into 300 ml water and extracted three times with ethyl ether. The pH of the extracted aqueous layer was adjusted to a pH of about 1 with aqueous 10 wt.

% hydrochloric acid and again extracted three times with ethyl ether. The organic layer was washed twice with saturated aqueous sodium bicarbonate, dried over magnesium sulfate and evaporated to dryness under vacuum affording 22.6 g of the title compound.

Similarly, by adapting the above procedure using the appropriately substituted-phenyl acetonitrile and ethyl-substituted phenyl acetate starting materials, the following compounds can be prepared: (5-chloro-3-trifluoromethylphenyi)-benzylcarbonyl-acetonitrile; (4-chloro-3-trifluoromethylphenyl)-benzylcarbonyl-acetonitrile; (2-bromo-3-trifluornmethylphenyl)-benzylcarbonyl-acetonitrile; (6-fluoro3-trifl uoromethyl phenyl)-benzylca rbonyl-acetonitrile; (4-methyl-3-trifl uoromethyl phenyl)-benzylca rbonyl-acetonitrile; (5-methoxy-3-trifl uoromethyl phenyl)-benzylcarbonyl-acetonitrile; (6-methyl-34rifluoromethylphenyl)-benzylcarbonyl-acetonitrile; (3,5-di-trifluoromethylphenyl)-benzylcarbonyl-acetonitrile; (3-difluoromethoxyphenyl)-benzylcarbonyl-acetonitrile;; (3-trifluoromethoxyphenyl)-benzylcarbonyl-acetonitrile; (3-trifl uorom ethylphenyl )-(4-fl uorobenzylca rbonyl)-acetonitrile; (3-trifluoromethylphenyl)-1 -naphthylmethylene-acetonitrile; (2-ch loro-3-methylph enyl)-benzylcarbonyl-acetonitrile; (4-ethyl-3-m ethylphenyl)-benzylca rbonyl-acetonitril e; (5-methoxy-3-ch lorophenyl)-benzylcarbonyl-acetonitrile; (3-iodophenyl)-benzylcarbonyl-acetonitrile; (3-difluoromethylthiophenyl)-benzylcarbonyl-acetonitrile; (3-trifl uoromethylth iophenyl)-benzylcarbo nyl-aceton itrile; (3,5-diethyoxyphenyl)-benzylcarbonyl-acetonitrile; (3-bromophenyl)-(2-nitrobenzylcarbonyl)-acetonitrile; (2-chloro-3-methylphenyl)-benzylcarbonyl-acetonitrile; (3-bromo-2-ethylphenyl)-naphth-1 -ylmethylenecarbonyl-acetonitrile;; (2,3-dimethylphenyl)-beta-naphth-1 -ylmethylcarbonyl-acetonitrile; (3-ch lorophenyl )-benzylca rbonyl-acetonitrile; (3-methylphenyl)-benzylcarbonyl-acetonitrile; (3-t-butoxyphenyl)-benzylcarbonyl-acetonitrile; (3-propylphenyl)-benzylcarbonyl-acetonitrile; (3-bromophenyl)-benzylcarbonyl-acetonitriíe; (3-iodophenyl)-(3-nitrobenzylcarbonyl)-acetonitrile; (3-trifluoromethylphenyl)-(2,3-dichlorobenzylcarbonyl)-acetonitrile; (3-methoxyphenyl)-1 -naphthylmethylenecarbonyl-acetonitrile; (3-trifluo romethyl )-(3-ch lo ro-8-fluoronaphth-1 -ylmethylenecarbonyl)-acetonitrile; (3-trifluoromethyl )-[(2-trifluoromethyl-3-methyl-8-methoxy-napth-1 -yl)methylenecarbonyl]-acetonitrile;; (3-trifluoromethyl)-(inden-1 -ylmethyienecarbonyl)-acetonitrile; and (3-trifluoromethyl)-(2-fluoroinden-1 -ylmethylenecarbonyl)-acetonitrile.

Example 2 2-Phen y/-3-oxo-4- (3-trffluoromethylphen yl)-5-amino-Z 3-dih ydrofuran In this example a solution containing 21.8 g of (3-trifluoromethylphenyl)-benzylcarbonyl-acetonitrile, dissolved in 60 ml of acetic acid was treated dropwise with a solution of 12.65 g of bromine in 20 ml of glacial acetic acid. The reaction mixture was stirred for about 16 hours at room temperature. The reaction mixture was poured into 250 ml of water and the resulting mixture was extracted three times with ethyl ether. The organic extracts were washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate and concentrated in vacuo to yield 8.4 g of white solid which was dried affording 7.0 g of the title compound.

Similarly, by adapting the above procedure to the compounds listed in Example 1, the following compounds can be prepared: 2-phenyl-3-oxo-4-(5-ch lo ro-3-trifluoromethylphenyl )-5-a mino-2,3-dihyd rofuran; 2-phenyl-3-oXo-4-(4-chloro-3-trifluoromethylphenyl)-5-amino-2,3-dihydrofuran; 2-phenyl-3-oXo-4-(2-bromo-3-trifluoromethylphenyl)-5-amino-2,3-dihydrofuran; 2-phenyl-3-oxo-4-(6-fl uoro-3-trifl uoromethylphenyl)-5-amino-2,3-dihydrofuran; 2-phenyl-3-oxo-4-(4-methyl-3-trifl uoromethyl phenyl-5-amino-2,3-dihydrofu ra n; 2-phenyl-3-oxo-4-(5-methoxy-3-trifluoromethylphenyl)-5-amino-2,3-dihydrofuran; 2-phenyl-3-oxo-4-(6-methyl-3-trifl uoromethylphenyl )-5-amino-2,3-dihydrof uran; 2-phenyl-3-oxo-4-(3,5-di-trifluoromethylphenyl)-5-amino-2,3-dihydrofuran; 2-phenyl-3-oxo-4-(3-difluoromethoxyphenyl)-5-amino-2,3-dihydrofuran;; 2-phenyl-3-oxo-4-(3-trifl uoromethoxyphenyl)-5-am ino-2,3-dihydrofu ran; 2-(4-fluorophenyl)-3-oxo-4-(3-trifluoromethylphenyl)-5-amino-2,3-dihydrofuran; 2-(1-naphthyl)-3-oxo-4-(3-trifluoromethylphenyl)-5-amino-2,3-dihydrofuran; 2-phenyl-3-oxo-4-(2-chloro-3-methylphenyl)-5-amino-2,3-dihydrofuran; 2-phenyl-3-oxo-4-(4-ethyl-3-methyl phenyl )-5-a mi no-2,3-dihyd rofu ran; 2-phenyl-3-oxo-4-(5-methoxy-3-chlorophenyl)-5-amino-2,3-dihydrofuran; 2-phenyl-3-oxo-4-(3-iodophenyl)-5-amino-2,3-dihydrofuran; 2-phenyl-3-oxo-4-(3-difluoromethylthiophenyl)-5-amino-2,3-dihydrofuran; 2-phenyl-3-oxo-4-(3-trifluoromethylthiophenyl)-5-am ino-2,3-dihydrofu ran; 2-phenyl-3-oxo-4-(3,5-diethoxyphenyl )-5-am ino-2,3-dihydrofu ran; 2-(2-nitrophenyl)-3-oxo-4-(3-bromophenyl)-5-amino-2,3-dihydrofuran;; 2-phenyl-3-oxo-4-(2-chloro-3-methylphenyl)-5-amino-2,3-dihydrofuran; 2-(1 -naphthyl)-3-oxo-4-(3-bromo-2-ethylphenyl)-5-amino-2,3-dihydrofuran; 2-(1 -naphthyl)-3-oxo-4-(2,3-dimethylphenyl)-S-amino-2,3-dihydrofuran; 2-phenyl-3-oxo-4-(3-chlorophenyl)-5-amino-2,3-dihydrofuran; 2-phenyl-3-oxo-4-(3-methylphenyl)-5-amino-2,3-dihydrofu ran; 2-phenyl-3-oxo-4-(3-butoxyphenyl)-S-amino-2,3-dihydrofuran; 2-phenyl-3-oxo-4-(3-propyl phenyl)-5-amino-2,3-dihydrofuran; 2-phenyl-3-oxo-4-(3-bromophenyl )-5-amino-2,3-dihydrofuran; 2-(3-nitrophenyl)-3-oxo-4-(3-iodophenyl)-5-amino-2,3-dihydrofuran; 2-(2,3-dichlorophenyl)-3-oXo-4-(3-trifluoromethylphenyl)-5-amino-2,3-dihydrofuran;; 2-(1 -naphthyl)-3-oxo-4-(3-methoxyphenyl)-5-amino-2,3-dihydrofuran; 2-(3-chloro-8-fluoronaphth-1 -yl)-3-oxo-4-(3-trifluoromethylphenyl )-5-amino-2,3-dihydrofuran; 2-(2-trifluoromethyl-3-methyl-8-methoxy-naphth-1 -yl )-3-oxo-4-(3-trifluoromethylphenyl )-5-amino-2,3dihydrofuran; 2-inden-1 -yI-3-oxo-4-(3-trifl uoromethyl phenyl)-S-amino-2,3-dihyd rofuran; and 2-(2-fluoroinden-1 -yl)-3-oxo-4-(3-trif luoromethylphenyi)-5-amino-2,3-dihydrof uran.

Example 3 2-Meth yl-3-oxo-4-(3-trffluoromethylphenyl)-5-amino-2,3-dihydrofuran A dry, 500-ml, three-neck, round-bottom flask equipped with a mechanical stirrer, addition funnel and a reflux condenser was charged with 100 ml of ethanol. To the stirred solvent were added 3.5 g of sodium.

After all the metal had dissolved, a solution of 13.0 g of ethyl L-(+)-lactate and 18.5 g of mtrifluoromethylphenyl-acetonitrile in 30 ml of ethanol was added dropwise to the reaction mixture. The mixture became a deep red and after the addition was complete, the mixture was heated at reflux overnight (about 18 hours). The mixture was then cooled to room temperature and added to 300 ml of water and the resulting mixture was acidified (pH about 1) with 10% hydrochloric acid. The mixture was then extracted with ether (three times) and the organic extracts were washed (two times) with saturated aqueous sodium bicarbonate, dried over magnesium sulfate and concentrated in vacuo to yield a thick oil. This oil was taken up in a mixture of ether/petroleum ether and the desired compound crystallized as a yellow powder.Two crops of crystals were collected to afford a total of 4.7 g of the title compound.

Similarly, by adapting the above procedure using the corresponding appropriately substituted starting materials the following compounds can be prepared: 2-ethyl-3-oxo-4-(3-trifluoromethyl phenyl)-S-amino-2,3-dihydrofuran; 2-ethyl-3-oxo-4-(5-chloro-3-trifluoromethylphenyl)-5-a mino-2,3-dihydrofu ran; 2-cyclo pentyl-3-oxo-4-(3-trifluoromethyl phenyl )-5-amino-2,3-dihydrofu ran; 2-vinyl-3-oxo-4-(3-trifl uoromethyl phenyl)-S-amino-2,3-dihydrofuran; 2-al lyl-3-oxo-4-(3-trifl uoromethyl phenyl )-S-amino-2,3-dihydrofuran; 2-allyl-3-oxo-4-(2-methoxy-3-trifluoromethyl phenyl )-5-amino-2,3-dihydrofuran; 2-trifl uoromethyl-3-oxo-4-(3-trifl uoromethyl phenyl )-5-amino-2,3-di hydrofuran; 2-methyl-3-oxo-4-(3-difluoromethoxyphenyl)-S-amino-2,3-dihydrofuran;; 2-methyl-3-oxo-4-(3-trifl uoromethoxyphenyl)-5-amino-2,3-dihydrofuran; 2-(2-chlorovi nyl)-3-oxo-4-(3-trifluoromethylphenyl )-5-amino-2,3-dihydrofuran; 2-(2-chlorovinyl)-3-oxo-4-(5-propoxy-3-trifluoromethylphenyl)-5-amino-2,3-dihydrofuran; 2-methyl-3-oxo-4-(2-methoxy-3-chlorophenyl)-5-amino-2,3-dihydrofuran; 2-ethyl-3-oxo-4-(2-chloro-3-fluorophenyl)-5-amino-2,3-dihydrofuran; 2-vinyl-3-oxo-4-(3-methyl-4-methoxyphenyl)-S-amino-2,3-dihydrofu ran; 2-al Iyl-3-oxo-4-(3,6-dimethyl phenyl)-5-amino-2,3-dihydrofu ran; 2-trifl uoromethyl-3-oxo-4-(3-trifl uoromethyl-4bromophenyl)-5-amino-2,3-dihydrofuran; 2-(2-chlorovi nyl)-3-oxo-4-(3-nitro-4-methyl phenyl)-5-amino-2,3-dihydrofu ran; 2-methyl-3-oxo-4-(3-methoxyphenyl)-5-amino-2,3-dihydrofu ran;; 2-methyl-3-oxo-4-(3-difluoromethylthiophenyl )-5-a mino-2,3-dihydrofu ran; 2-methyl-3-oxo-4-(3-difluoromethylthiophenyl-5-amino-2,3-dihydrofuran; 2-ethyl-3-oxo-4-(3-chlorophenyl)-5-amino-2,3-dihydrofuran; 2-vinyl-3-oxo-4-(3-methylphenyl-5-amino-2,3-dihydrofu ran; 2-al Iyl-3-oxo-4-[3,5-di(trifl uoromethyl)-phenyl]-5-amino-2,3-dihydrofuran; 2-trifluoromethyl-3-oxo-4-(4-fluorophenyl)-5-amino-2,3-dihydrofuran; 2-(2-chlorovinyl)-3-oxo-4-(2-bromophenyl)-3-oxo-5-amino-2,3-dihydrofuran; 2-propyl-3-oxo-4-(2-methoxy-3-chlorophenyl)-5-amino-2,3-dihydrofuran; 2-butyl-3-oxo-4-(2-chloro-3-fluorophenyl)-5-amino-2,3-dihydrofuran; 2-vinyl-3-oxo-4-(3-chloro-4-methoxyphenyl)-5-amino-2,3-dihydrofuran; 2-allyl-3-oxo-4-(3,5-dimethyl phenyl)-5-amino-2,3-dihydrofuran; ; 2-(trifluoromethyl)-3-oxo-4-(3-trifluoromethyl-5-bromophenyl)-5-amino-2,3-dihdyrofuran; 2-(2-chlorovinyl )-3-oXo-4-(3-fluoro-4-methylphenyl)-3-oxo-5-amino-2,3-dihydrofuran; 2-phenyl-3-oxo-4-(3-methoxyphenyl)-S-amino-2,3-dihydrofuran; 2-methyl-3-oxo-4-(3,5-difluorophenyl)-5-amino-2,3-dihydrofuran; 2-vinyl-3-oxo-4-(3,5-diethyl phenyl)-5-amino-2,3-d ihydrofu ran; 2-al Iyl-3-oxo-4-(3-propoxyphenyl)-5-a m ino-2,3-dihydrofu ran; 2-trifl uoromethyl-3-oxo-4-(3-fluorophenyl )-S-amino-2,3-dihydrofuran; 2-propyl-3-oxo-4-(3-bromophenyl)-3-oxo--S-amino-2,3-dihydrofu ran; 2-phenyl-3-oxo-4-(2-iodo-3-fl uorophenyl)-5-ami no-2,3-dihyd rofuran; 2-benzyl-3-oxo-4-(2-isopropoxy-34rifl uoromethylphenyl)-S-am ino-2,3-dihyd rofuran; 2-(3-chlorophenyl)-3-oxo-4-(2,3-dimethlphenyl)-S-amino-2,3-dihydrofuran;; 2-naphth-1 -yl-3-oxo-4-(3-trifluoromethyl-4-bromophenyl)-5-amino-2,3-dihydrofuran; 2-(3-methyl phenyl)-3-oxo-4-(3-butyl-4-methylphenyl)-3-oxo-5-am ino-2,3-dihydrofu ran; 2-(3-fluorophenyl )-3-oxo-4-(3-chlorophenyl)-5-ami no-2,3-dihydrofu ran; 2-(2,3,5-trifluorophenyl-3-oxo-4-(3-trifl uo romethylphenyl)-S-amino-2,3-dihydrofu ran; 2-(3-methyl napth-1 -yl )-3-oxo-4-(3-trifl uoromethylphenyl)-5-amino-2,3-dihydrofu ra n; 2-(2'-ch lorovinyl )-3-oxo-4-(3-trifl uoromethylphenyl)-5-amino-2,3-dihydrofuran; 2-fl uoromethyl-3-oxo-4-'3-trifl uoromethylphenyl)-5-amino-2,3-dihydrofu ran; 2-methoxymethylene-3-oxo-4-(3-trifluoromethylphenyl)-S-amino-2,3-dihyd rofuran;; 2-propoxymethylene-3-oxo-4-(3-trifl uoromethylphenyl)-5-am ino-2,3-dihydrofuran; 2-ethoxymethylene-3-oxo-4-(3-trif luoromethylphenyl )-5-amino-2,3-dihydrof uran; 2-(2-methoxypropyl )-3-oxo-4-(3-trifl uoromethylphenyl )-5-amino-2,3-dihydrofuran; 2-methylth iomethyl ene-3-oxo-4-(3-trifluoromethyl phenyl)-S-amino-2,3-dihydrofu ran; and 2-(1 -propylthioethyl)-3-oxo-4-(3-trifluoromethylphenyl)-S-amino-2,3-dihydrofuran.

Example 4 (3-Trifiuoromethylphenyl)-methoxyacetyl-acetonitrlle In this example 5.6 grams of metallic sodium was added to 120 ml of anhydrous ethanol at room temperature under nitrogen atmosphere resulting in the evolution of hydrogen. After evolution of hydrogen was completed a mixture containing 30 g of (3-trifluoromethylphenyl)-acetonitrile and 18.5 g of methyl methoxyacetate in anhydrous ethanol was added and the resulting mixture refluxed for 3 to 4 hours. The mixture was then added to 300 ml of water and extracted three times with petroleum ether. The remaining aqueous phase was acidified with aqueous 10% hydrochloric acid to about pH 1 and extracted three times with ethyl ether.The ethyl ether extracts were combined, washed twice with saturated aqueous sodium bicarbonate, dried over magnesium sulfate and concentrated by evaporation. The concentrate was evaporated under high vacuum affording an oil which was triturated with ethyl ether. This mixture was then filtered to remove solids and the filtrate evaporated under vacuum affording 36.9 g of the title compound as a brown solid.

Similarly, by adapting the above procedure but using other (substituted and disubstituted phenyl) acetonitriles in place of (3-trifluoromethylphenyl)acetonitrile the corresponding substituted and disubstituted phenyl analogs of the title compound can be prepared.

Example 5 (3- Trff/uorom eth ylphen yl)-2-m ethoxyiso va/eryl-aceton,trile In this example 10 g of (3-trifluoromethylphenyl)-methoxyacetyl-acetonitrile was added dropwise to a slurry of 1.87 g of sodium hydride in 20 ml of tetrahydrofuran at about 0 C under a nitrogen atmosphere, resulting in the evolution of hydrogen. After no further evolution of hydrogen was observed, the mixture was cooled to about -78 C and 24.3 ml of 1.6M n-butyllithium in hexane was added dropwise. The mixture was stirrred for 1-1/2 hours at -78 C and then stirred at about 0-4"C for twenty minutes. After this 3.9 ml (about 6.64 g) of 2-iodopropane was added dropwise and the mixture stirred overnight (about 14-16 hours).The mixture was then added to water, acidified with aqueous 10% hydrochloric acid and extracted three times with ethyl ether. The extracts were combined, dried over magnesium sulfate and concentrated under vacuum affording 11.4 g of the title compound as an oil.

Similarly, by adapting the same procedure but using the appropriate alkyl, aryl or substituted aryl, iodide, bromide, or chloride in place of iodopropane the following compounds can be prepared: (3-trifluoromethylphenyl)-(2-methoxy-3-phenylpropionyl)acetonitrile; (3-trifluoromethyl phenyl )-[2-methoxy-3-(2-fluo rophenyl)propionyl]acetonitrile; (3-trifluoromethyl phenyl)-[2-methoxy-3-(3-methylphenyl )propionyl]acetonitrile; (3-trifluoromethylphenyl)-[2-methoxy-3-(2-ethoxyphenyl)propionyl]acetonitrile; (3-trifluoromethylphenyl)-[2-methoxy-3-(3-nitrophenyl)propionyljacetonitrile; (3-trifluoromethylphenyl)-[2-methoxy-3-(2-trifluoromethylphenyl)propionyl]acetonitrile; (3-trifluoromethylphenyl)-[2-methoxy-3-(2-chloro-3-propylphenyl)propionyl]acetonitrile;; (3-trifluoromethylphenyl)-[2-methoxy-3-(2-nitro-3-methoxyphenyl)propionyl]acetonitriie; (3-trifluoromethylphenyl)-[2-methoxy-3-(2-fluoro-3-2',2'-dichloroethylphenyl)propionyi]acetonitrile; (3-trifluoromethylphenyl)-[2-methoxy-3-(2,3-dichloro-6-methylphenyl)propionyl]acetonitrile; (3-trifluoromethylphenyl)-(2-methoxy-4-phenylbutyryl)acetonitrile; (3-trifluoromethylphenyl)-[2-methoxy-5-(2-bromophenyl)valeryl]acetonitrile; (3-trifl uoromethyl phenyl )-(2-methoxy-3-methyl-4-phenyl butyryl)acetonitrile; (3-trifluoromethy)-(2-methoxy-3-naphth-1 -ylpropionyl)acetonitrile; (3-trifluoromethyl)-[2-methoxy-3-(2-fluoronaphth-1 -yl)propionyl]acetonitrile; (3-trif luoromethyl)-[2-methoxy-3-(3-butyl naphth-l-yl )propionyl]acetonitrile;; (3-trifluoromethyl)-[2-methoxy-3-(5-methoxynaphth-1 -yl)propionyl]acetonitrile; (34rifluoromethyl)-[2-methoxy-3-(6-nitronaphth-1 -yl)propionyl]acetonitrile; (3-trifluoromethyl)-[2-methoxy-3-(7-trifluoromethyinaphth-1 -yl)propionyl]acetonitrile; (3-trifluoromethyl)-[2-methoxy-3-(2-chloro-8-methyl naphth-1 )propionyl]acetonitrile; (3-trifl uoromethyl)-[2-methoxy-3-(3-methoxy-5-nitro-7-fluoromethyinaphth-1 -yl)propionyl]acetonitrile; (3-trifluoromethyl )-(2-methoxy-4naphth-1 -yl butyryl )acetonitrile; (3-trifluoromethyl )-[2-methoxy-5-(84luoronaphth-1 -yl)valeryl]acetonitrile;; (3-trifluoromethyl)-[2-methoxy-3-methyl-3-(7-methoxynaphth-1 -yl)propionyl]acetonitrile; (3-trifluoromethylphenyl)-(2-methoxy-3-inden-1 -ylpropionyl)acetonitrile; and (3-trifluoromethylphenyl)-[2-methoxy-3-(2-fluoroinden-1 -yl)propionyl]acetonitrile.

Similarly, by adapting the above procedure using other (mono or disubstituted phenyl) (methoxyacetyl)acetonitriles in place of (3-trifluoromethylphenyl)-(2-methoxyacetyl)acetonitrile the corresponding mono ordisubstituted phenyl derivatives of the above compounds can be prepared.

Example 6 24soprop yl-3-oxo-4-(3-trffluoromethylphen yl)-5-amin 0-2,3-dihydrofuran In this example, a mixture containing 11.4 g of (3-trifluoromethylphenyl)-(2-methoxyisovaleryl)acetonitrile and 7.8 g of concentrated sulfuric acid in 50 ml of acetic acid was warmed to reflux for 30 minutes and then concentrated by evaporation under vacuum. The concentrate was mixed with diethylether, washed three times with 1N aqueous sodium hydroxide, dried over magnesium sulfate and concentrated by evaporation affording an oil. The oil was triturated in 20% (vol.) ethyl acetate:80% petroleum ether and allowed to stand overnight (14-16 hours). The solids were collected by filtration and washed three times with 20% (vol.) ethyl acetate:80% petroleum ethyl affording 2.9 g of the title compound.

Similarly, by adapting the above procedure using 3-trifluoromethylphenyl-dimethoxyacetyl-acetonitrile, which can be prepared via the procedure of Example 1 and the other compound products indicated in Example 5, the following compounds can be prepared: 2-methoxy-3-oxo-4-(3-trifl uoromethylphenyl )-S-amino-2,3-dihydrofuran; 2-(2-fluorobenzyl)-3-oxo-4-(3-triflu oromethylphenyl )-5-amino-2,3-dihydrofuran; 2-(3-methyl benzyl )-3-oxo-4-(3-trifluoromethyl phenyl )-5-amino-2,3-dihydrofuran; 2-(2-ethoxybenzyl )-3-oxo-4-(3-trifluoromethylphenyl)-5-ami no-2,3-dihydrofuran; 2-(3-nitrobenzyl)-3-oXo-4-(3-trifluoromethylphenyl)-5-amino-2,3-dihydrofuran; 2-(4-fluorobenzyl )-3-oxo-4-(3-trifl uoromethylphenyl)-5-amino-2,3-dihydrofu ran;; 2-(2-trifluoromethylbenzyl)-3-oXo-4-(3-trifluoromethylphenyl)-5-amino-2,3-dihydrofu ran; 2-(2-chloro-3-propylphenyl)-3-oXo-4-(3-trifluoromethylphenyl)-5-amino-2,3-dihydrofuran; 2-(2-nitro-3-methoxyphenyl)-3-oxo-4-(3-trifluoromethylphenyl)-S-amino-2,3-dihydrofuran; 2-(2-fluoro-3-2',2'-dichloroethylbenzyl)-3-oxo-4-(3-trifluoromethylphenyl)-S-amino-2,3-dihydrofuran; 2-(2,3-dich loro-6-methyl benzyl )-3-oxo-4-(3-trifl uoromethylphenyl)-5-amino-2,3-dihydrofuran; 2-(beta-phenethyl)-3-oxo-4-(3-trifl uoromethyl phenyl )-5-ami no-2,3-dihydrofu ran; 2-[3-(2-bromophenyl)propyl]-3-oxo-4-(3-trifluoromethylphenyl)-5-amino-2,3-dihydrofuran; 2-[1 -methyl-2-(phenyl)ethyl]-3-oxo-4-(3-trif luoromethylphenyl )-5-amino-2,3-dihyd rofu ran;; 2-naphth-1-ylmethylene-3-oxo-4-(3-trifluoromethylphenyl)-5-amino-2,3-dihydrofuran; 2-(2-fluoronaphth-1-ylmethylene)-3-oxo-4-(3-trifluoromethylphenyl)-5-amino-2,3-dihydrofuran; 2-(3-butylnaphth-1-ylmethylene)-3-oxo-4-(3-trifluoromethylphenyl)-5-amino-2,3-dihydrofuran; 2-(5-methoxynaphth-1-ylmethylene)-3-oxo-4-(3-trifluoromethylphenyl)-5-amino-2,3-dihydrofuran; 2-(6-nitronaphth-1 -yl methylene-)-3-oxo-4-(3-trifl uoromethyl phenyl)-5-amino-2,3-dihydrofuran; 2-(7-trifluoromethylnaphth-1-ylmethylene)-3-oXo-4-(3-trifluoromethylphenyl)-5-amino-2,3-dihydrofuran; 2-(2-chloro-8-methyinaphth-1 -ylmethylene)-3-oxo-4-(3-trifluoromethylphenyl )-5-amino-2,3-dihydrofu ran; 2-(3-methoxy-5-nitro-7-fluoromethylnaphth-1-yl)-3-oxo-4-(3-trifluoromethylphenyl)-5-amino-2,3dihydrofuran;; 2-(beta-naphth-1 -ylethyl)-3-oxo-4-(3-trifluoromethyl phenyl)-5-amino-2,3-dihydrofu ran; 2-[beta-(8-fluoronaphth-1 -yl)ethyl]-3-oXo-4-(3-trifluoromethylphenyl)-5-amino-2,3-dihydrofuran; 2-[1-(7-methoxynaphth-1-yl)ethyl]-3-oxo-4-(3-trifluoromethylphenyl)-5-amino-2,3-dihydrofuran; 2-inden-1-ylmethylene-3-oxo-4-(3-trifluoromethylphenyl)-5-amino-2,3-dihydrofuran; and 2-(2-fluoroinden-1-ylmethylene)-3-oxo-4-(3-trifluoromethylphenyl)-5-amino-2,3-dihydrofuran.

Similarly, by adapting the above procedure using the corresponding mono- and disubstituted analogs of the starting material for the above compounds the corresponding 4-(3-methylphenyl); 4-(3-beta fluoroethoxyphenyl); 4-(3-difluoromethylenethiophenyl); 4-(3-chlorophenyl); 4-(2-bromo-3 trifluoromethyiphenyl)- and 4-(2-methyl-3-difluoromethylenethiophenyl analogs of the above compounds can be prepared.

Example 7 2-Phenyl-3-oxo-4-(3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran In this example about 1 g of solid sodium hydroxide in 4.0 ml of water was added to a mixture of 3 g of 2-phenyl-3-oxo-4-(3-trifluoromethylphenyl)-5-amino-2,3-dihydrofuran; in 50 ml of methylene chloride at room temperature followed by the addition of 1.19 g of dimethyl sulfate and 0.21 g of benzyltriethyl ammonium chloride. The resulting two-phase mixture was stirred at room temperature for about two hours and then washed three times with water, dried over magnesium sulfate and then concentrated by evaporation under vacuum. The residue was then purified by chromatography over silica gel eluting with mixtures of tetrahydrofuran and chloroform affording the title compound.

Similarly, by adapting the above procedure using the products listed in Examples 2,3 and 6 as starting materials, the corresponding 5-methylamino homologs thereof can be prepared, for example: 2-phenyl-3-oXo-4-(5-chloro-3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran; 2-phenyl-3-oxo-4-(4-chloro-34rifluoromethylphenyl)-S-methylamino-2,3-dihydrofuran; 2-phenyl-3-oXo-4-(2-bromo-3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran; 2-phenyí-3-oxo-4-(6-fluoro-3-trifl uoromethylphenyl )-5-methyla mino-2,3-dihyd rofu ran; 2-phenyl-3-oxo-4-(4-methyl-3-trifl uo romethylphenyl)-5-methyla mi no-2,3-dihydrofu ran; 2-phenyl-3-oXo-4-(5-methoxy-3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofu ran;; 2-phenyl-3-oxo-4-(6-methyl-3-trifl uoromethyl phenyl )-5-methylamino-2,3-dihydrofu ran; 2-phenyl-3-oxo-4-(3,5-di-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran; 2-ph enyl-3-oxo-4-(3-difl uoromethoxyphenyl)-S-methylamino-2,3-dihydrofu ran; 2-phenyl-3-oxo-4-(3-trifl uo romethoxyphenyl)-5-methylamino-2,3-dihydrofu ran; 2-phenyl-3-oxo-4-(3-trifl uoromethylthiophenyl)-5-methylamino-2,3-dihydrofu ran; 2-(4-fluorophenyl)-3-oXo-4-(3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran; 2-(1-naphthyl)-3-oxo-4-(3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran; 2-phenyl-3-oxo-4-(2-chloro-3-methylphenyl)-5-methylamino-2,3-dihydrofuran;; 2-phenyl-3-oxo-4-(4-ethyl -3-methyl phenyl)-5-methyla mi no-2,3-dihydrofu ran; 2-phenyl-3-oxo-4-(5-methoxy-3-chlorophenyl)-5-methylamino-2,3-dihydrofuran; 2-phenyl-3-oxo-4-(3-iodoph enyl)-S-methyl amino-2,3-dihydrofu ran; 2-phenyl-3-oxo-4-(3-difluoromethylthiophenyl)-5-methylamino-2,3-dihydrofuran; 2-phenyl-3-oxo-4-(3-trifluo romethylphenyl )-5-methylam ino-2,3-dihydrofuran; 2-phenyl-3-oxo-4-(3,5-diethoxyphenyl)-5-methylamino-2,3-dihydrofuran; 2-(2-nitrophenyl)-3-oxo-4-(3-bromophenyl)-5-methylamino-2,3-dihydrofuran; 2-phenyl-3-oxo-4-(2-chloro-3-methylphenyl)-5-methylamino-2,3-dihydrofuran; 2-(1-naphthyl)-3-oxo-4-(3-bromo-2-ethylphenyl)-5-methylamino-2,3-dihydrofuran; 2-(1-naphthyl)-3-oxo-4-(2,3-dimethylphenyl)-5-methylamino-2,3-dihydrofuran;; 2-phenyl-3-oxo-4-(3-chlorophenyl)-5-methylamino-2,3-dihydrofuran; 2-phenyl-3-oxo-4-(3-methylphenyl)-5-methylamino-2,3-dihydrofuran; 2-phenyl-3-oxo-4-(3-b utoxyph enyl)-5-methylamino-2,3-dihydrofu ran; 2-phenyl-3-oxo-4-(2-propylphenyl)-5-methylamino-2,3-dihydrofuran; 2-phenyl-3-oxo-4-(3-bromophenyl)-5-methylamino-2,3-dihydrofuran; 2-(3-nitrophenyl)-3-oxo-4-(3-iodophenyl)-5-methylamino-2,3-dihydrofuran; 2-(2,3-dichlorobenzyl)-3-oxo-4-(2-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran; 2-(1-naphthyl)-3-oxo-4-(3-methoxyphenyl)-5-methylamino-2,3-dihydrofuran; 2-(3-chloro-8-fluoronaphth-1-yl)-3-oxo-4-(3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran; 2-(2-trifluo ro m ethyl-3-methyl-8-methoxynaphth-1 -yl)-3-oxo-4-(3-trifluoromethylphenyl)-5-methylamino2,3-dihydrofuran;; 2-ìnden-1 -yl-3-oXo-4-(3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran; 2-(2-fluoroinden-1-yl)-3-oxo-4-(3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran; 2-methyl-3-oxo-4-(3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran; 2-ethyl-3-oxo-4-(3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran; 2-ethyl-3-oxo-4-(5-ch Ioro-3-trifluoromethylphenyl)-5-methylamino 2,3-di hydrofu ran, 2-cyclopentyl-3-oXo-4-(3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran; 2-vinyl-3-oxo-4-(3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran; 2-allyl-3-oxo-4-(3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran; 2-allyl-3-oxo-4-(2-methoxy-3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran;; 2-trifluoromethyl-3-oxo-4-(3-trifl uoromethylphenyl)-5-methylam ino-2,3-dihydrofu ran; 2-methyl-3-oxo-4-(3-difl uoromethoxyphenyl)-S-methylamino-2,3-dihydrofura n; 2-methyl-3-oxo-4-(3-trifluoromethoxyphenyl)-5-methylamino-2,3-dihydrofuran; 2-(2-ch lorovinyl)-3-oxo-4-(3-trifluoromethylphenyl)-5-methylam i no-2,3-dihydrofu ran; 2--chlorovinyl) 3 oxo 4 (5 nitro-3-trifiuoromethylphenyl)-S-methylam I no-2,3-dihydrofuran, 2-methyl-3-oxo-4-(2-methoxy-3-chlorophenyl)-5-methylamino-2,3-dihydrofuran; 2-ethyl-3-oxo-4-(2-chloro-3-fluorophenyl)-5-methylamino-2,3-dihydrofuran; 2-vinyl-3-oxo-4-(3-methyl-4-methoxyphenyl)-5-methylamino-2,3-dihydrofuran;; 2-al Iyl-3-oxo-4-(3,6-dimethyl phenyl )-5-methyl ami no-2,3-dihydrofu ran; 2-trifluoromethyl-3-oxo-4-(3-trifl uoromethyl-4-bromophenyl)-5-methylamino-2,3-dihydrofu ran; 2-(2-chlorovi nyl)-3-oxo-4-(3-nitro-4-methyl phenyl)-3-oxo-5-methylam ino-2,3-dihydrnfu ran; 2-methyl-3-oxo-4-(3-methoxyphenyl)-5-methylamino-2,3-dihydrofuran; 2-methyl-3-oxo-4-(3-difluoromethylthiophenyl)-5-methylamino-2,3-dihydrofuran; 2-methyl-3-oxo-4-(3-trifluoromethylthiophenyl)-5-methylamino-2,3,dihydrofuran; 2-ethyl-3-oxo-4-(3-chlorophenyl)5-methylamino-2,3,dihydrofuran; 2-vinyl-3-oxo-4-(3-methylphenyl)-5-methylamino-2,3-di hydrofuran; 2-allyl-3-oXo-4-[3,5-di(trifluoromethyl)phenyl]-5-methylamino-2,3-dihydrofuran;; 2-trifluoromethyl-3-oxo-4-(4-fluorophenyl)-5-methylamino-2,3-dihydrofuran; 2-(2-chlorovinyl)-3-oxo-4-(2-bromophenyl)-3-oxo-5-methylamino-2,3-dihydrofuran; 2-propyl-3-oxo-4-(2-methoxy-3-chlorophenyl)-5-methylamino-2,3-dihydrofuran; 2-butyl-3-oxo-4-(2-chloro-3-fluorophenyl)-5-methylamino-2,3-dihydrofuran; 2-vinyl-3-oxo-4-(3-chloro-4-methoxyphenyl)-5-methylamino-2,3-dihydrofuran; 2-allyl-3-oxo-4-(3,6-dimethylphenyl)-5-methylamino-2,3-dihydrofuran; 2-trifluoromethyl-3-oXo-4-(3-trifluoromethyl-5-bromophenyl)-5-methylamino-2,3-dihydrofuran; 2-(2-chlorovinyl)-3-oxo-4-(3-fluoro-4-methylphenyl)-3-oxo-5-methylamino-2,3-dihydrofuran; 2-phenyl-3-oxo-4-(3-methoxyphenyl)-5-methylamino-2,3-dihydrofuran; 2-methyl-3-oxo-4-(3,5-difluorophenyl)-5-methylamino-2,3-dihydrofuran; 2-vinyl-3-oxo-4-(3,5-diethylphenyl)-5-methylamino-2,3-dihydrofuran;; 2-allyl-3-oXo-4-(3-propoxyphenyl)-5-methylamino-2,3-dihydrofuran; 2-trifluoromethyl-3-oxo-4-(3-fluorophenyl)-5-methylamino-2,3-dihydrofuran; 2-propyl-3-oxo-4-(2-bromophenyl)-3-oxo-5-methylamino-2,3-dihydrofuran; 2-phenyl-3-oxo-4-(2-iodo-3-fluorophenyl)-5-methylamino-2,3-dihydrofuran; 2-benzyl-3-oxo-4-(2-isopropoxy-3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran;, 2-(3-chlorophenyl)-3-oxo-4-(2,3-dimethylphenyl)-5-methylamino-2,3-dihydrofuran; 2-naphth-1-yl-3-oxo-4-(3-trifluoromethyl-4-bromophenyl)-5-methylamino-2,3-dihydrofuran; 2-(3-methylphenyl)-3-oxo-4-(3-butyl-4-methylphenyl)-3-oxo-5-methylamino-2,3-dihydrofuran; 2-(3-fluorophenyl)-3-oxo-4-(3-chlorophenyi )-5-methylamino-2,3-dihydrofuran; 2-(2,3,5-trifl uorophenyl)-3-oxo-4-(3-trifl uoromethylphenyl)-5-m ethylamino-2,3-dihydrofuran;; and 2-(3-methylnaphth-1-yl)-3-oxo-4-(3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran; 2-(1'-chlorovinyl)-3-oxo-4-(3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran; 2-fluoromethyl-3-oxo-4-(3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran; 2-methoxymethylene-3-oxo-4-(3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran; 2-propoxymethylene-3-oxo-4-(3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran; 2-ethoxymethylene-3-oxo-4-(3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran; 2-(2-methoxypropyl )-3-oxo-4-(3-trifluoro methylphenyl)-5-methylamino-2,3-dihydrofuran; 2-methylthiomethylene-3-oxo-4-(3-trifl uoromethylphenyl)-5-methylamino-2,3-dihydrofuran; and 2-(1-propylthioethyl)-3-oxo-4-(3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran.

2-benzyl-3-oxo-4-(3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran; 2-(2-fluorobenzyl)-3-oxo-4-(3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran; 2- (3-methyl benzyl)-3-oxo-4-(3-trifluoromethyl phenyl )-5-methylamino-2,3-dihydrofu ran; 2-(2-ethoxybenzyl)-3-oxo-4-(3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran; 2-(3-nitrobenzyl)-3-oxo-4-(3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran; 2-(4-fluorobenzyl )-3-oxo-4-(3-trifluoromethyl phenyl)-5-methylamino-2,3-dihydrofu ran; 2-(2-trifluoromethylbenzyl)-3-oxo-4-(3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran; 2-(chloro-3-propyl phenyl)-3-oxo-4-(3-trifl uoromethyl phenyl )-5-methylamino-2,3-dihydrofuran; 2-(2-nitro-3-methoxyphenyl)-3-oxo-4-(3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran;; 2-(2-f luoro-3-2',2'-dichloroethyl benzyl)-3-oxo-4-(3-trif luoromethylphenyl )-5-methylamino-2,3- dihydrofuran; 2-(2,3-dichloro-6-methylbenzyl)-3-oxo-4-(3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran; 2-(beta-phenethyl)-3-oxo-4-(3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran; 2-[3-(2-bromophenyl)propyl]-3-oxo-4-(3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran; 2-[1-methyl-2-(phenyl)ethyl]-3-oxo-4-(3-trifluoromethylphenyl)-5-meethylamino-2,3-dihydrofuran; 2-naphth-1-ylmethylene-3-oxo-4-(3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran; 2-(2-fluoronaphth-1-ylmethylene)-3-oxo-4-(3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran; 2-(3-butynaphth-1-ylmethylene)-3-oxo-4-(3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran;; 2-(5-methoxynaphth-1-ylmethylene)-3-oxo-4-(3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran; 2-(6-nitronaphth-1-ylmethylene)-3-oxo-4-(3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran; 2-(7-trifluoromethylnaphth-1-ylmethylene)-3-oxo-4-(3-trifluoromethylphenyl)-5-methylamino-2,3dihydrofuran; 2-(2-chloro-8-methylnaphth-1 -yl methylene)-3-oxo-4-(3-trifluoromethyl phenyl)-5-methylam ino-2,3dihydrofuran; 2-(3-methoxy-5-nitro-7-fluoromethylnaphth-1-yl)-3-oxo-4-(3-trifluoromethylphenyl)-5-methylamino-2,3dihydrofuran; 2-methoxy-3-oxo-4-(3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran; 2-(beta-naphth-1 -ylethyl)-3-oxo-4-(3-trifluoromethyl phenyl)-S-methylamino-2,3-dihydrofuran; 2-[beta-(8-fluoronaphth-1-yl)ethyl]-3-oxo-4-(3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran; ; 2-[1-(7-methoxynaphth-1-yl)ethyl]-3-oxo-4-(3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran; 2-inden-1-ylmethylene-3-oxo-4-(3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran; and 2-(2-fluoroinden-l -ylmethylene)-3-oxo-4-(3-trifluoromethylphenyl)-S-methylamino-2,3-dihydrofuran.

Similarly, by approximately doubling the amount of dimethylsulfate and increasing the reaction time, the corresponding 5-dimethylamino homologs of the above compounds can be prepared. Similarly, by using diethylsulfate in place of dimethylsulphate the corresponding 5-ethylamino and 5-diethylamino homologs of the above compounds can be prepared.

Example 8 2-r2-Fluorophenyl)-3-oXo-4-r3-trifluoromethylphenylJ-5-allylamino-2,3-dihydrofuran One gram of sodium hydroxide in 4.0 ml of water was added to a mixture of 4.0 g of 2-(2-fluorophenyl)-3 oxo-4-(3-trifluoromethylphenyl)-S-amino-2,3-dihydrofuran in 80 ml of methylene chloride at room temperature followed by the addition of 1.44 g of allyl bromide and 0.27 g of benzyltriethylammonium chloride. The resulting two-phase mixture was stirred at room temperature for about 18 hours after which time it was washed three times with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by chromatography over silica gel eluting with chloroform to yield 2.5 g of the title compound.

Similarly, by applying this procedure to the products listed in Examples 2,3 and 6, the corresponding 5-allylamino analogs thereof can be prepared. Similarly, by approximately doubling the amount of ally bromide and sodium hydroxide, the corresponding 5-diallylamino analogs thereof can be prepared.

In a like manner, by using ethyl bromide in place of allyl bromide, the corresponding 5-ethylamino and 5-diethylamino analogs can be prepared.

Similarly, by following the same procedure by respectively using methoxymethyl bromide, ethylthiomethyl bromide, methyl bromoacetate, methyl 2-bromobutyrate, 1,5-dibromopentane, and cis-1,4 dibromobut-1 ,3-diene in place of alkyl bromide the corresponding 5-methoxymethylamino, 5ethylthiomethylamino, 5-methoxycarbonylmethylamino, 5-(1 -methoxycarbonylpropylamino), 5-piperidin-i - yl and S-pyrrol-1-yl analogs ofthe products listed in Examples 2,3 and 6 can be prepared for example:: 2-phenyl-3-oxo-4-(3-trifluoromethylphenyl)-S-methoxymethylamino-2,3-dihydrofuran; 2-methyl-3-oxo-4-(3-trifluoromethylphenyl)-S-methoxymethylamino-2,3-dihydrofuran; 2-ethyl-3-oxo-4-(3-trifl uoromethyl phenyl )-5-methoxymethylam ino-2,3-dihydrofu ran; 2-phenyl-3-oxo-4-(3-trifl u oromethyl phenyl)-5-ethylthiomethylamino-2,3-dihydrofuran; 2-meth oxy-3-oxo-4-(3-trifl uoromethyl phenyl )-S-ethylth iomethylamino-2,3-dihydrofuran; 2-methyl-3-oxo-4-(3-trifl uoromethyl phenyl )-5-ethylth iomethyla mino-2,3-dihydrofuran; 2-ethoxymethyl ene-3-oxo-4-(3-trifluoromethylphenyl )-5-ethylthiomethyla mino-2,3-dihydrofu ran; 2-ethyl-3-oxo-4-(3-trifluoromethyl phenyl )-5-ethylthiomethylamino-2,3-dihydrofuran;; 2-phenyl-3-oxo-4-(3-trifl uoromethylphenyl)-5-methoxycarbonylmethylamino-2,3-dihydrofu ran; 2-methyl-3-oxo-4-(3-trifluoromethylphenyl)-S-methoxycarbonylmethylamino-2,3-dihydrofuran; 2-methylthiomethylene-3-oxo-4-(3-trifluoromethylphenyl)-S-methoxycarbonylmethylamino-2,3- dihydrofuran; 2-ethyl-3-oxo-4-(3-trifluoromethylphenyl)-5-m ethoxycarbonylmethylam ino-2,3-dihydrofu ran; 2-phenyl-3-oXo-4-(3-trifluoromethylphenyl)-5-(1-methoxycarbonylprop-1 -yl)amino-2,3-dihydrofuran; 2-methyl-3-oxo-4-(3-trifluo romethyl phenyl)-5-(1 -methoxycarbonylprop-1 -yl)amino-2,3-dihydrofuran; 2-fluoro-3-oxo-4-(3-trifluoromethylphenyl)-5-(1 -methoxycarbonylprop-1 -yl)amino-2,3-dihydrofuran;; 2-ethyl-3-oxo-4-(3-trifluoromethylphenyl)-5-( 1 -methoxycarbonylprop-1 -yl)amino-2,3-dihydrofuran; 2-naphth-1 -yl-3-oxo-4-(3-trifluoromethylphenyl)-5-(1 -methoxycarbonylprop-1 -yl)amino-2,3-dihydrofuran; 2-inden-1 -yl-3-oxo-4-(3-trifluoromethylphenyl)-5-(1 -methoxycarbonylprop-1 -yl)amino-2,3-dihydrofuran, 2-phenyl-3-oxo-4-(3-trifluoromethylphenyl)-S-piperidin-1 -yl-2,3-dihydrofuran; and 2-phenyl-3-oxo-4-(3-trifl uoromethylphenyl)-5-pyrrol-l -yl-2,3-dihyd rofu ran, etc.

Similarly, by applying the above procedures using the 5-methylamino products of Example 7 as starting materials, the corresponding 5-(N-methyl-N-allylamino), 5-(N-methyl-N-ethylamino), 5-(N-methyl-N- methoxymethylamino), 5-(N-methyl-N -ethylthiomethylami no), 5-(N-methyl-N- methoxycarbonylmethylamino), and S-(N-methyl-N-1 '-methoxycarbonylpropylamino) analogs can be prepared.

Example 9 Lithium salt of 2-phenyl-3-oxo-4-(3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran (R=-CH3, R2=Li) In this example, 5.4 ml of 1.6M n-butyllithium in hexane was added dropwise to a stirred solution containing 2.86 g of 2-phenyl-3-oxo-4-(3-trifluoromethylphenyl)-5-amino-2,3-dihydrofuran in 25 ml of tetrahydrofuran at -30 C. The resulting mixture was stirred for 20 minutes and then concentrated in vacuo affording 2.8 g of the title compound as a light brown solid. Elemental analysis: calculated, C-63.74, H-3.84, N-4.13; found, C-61.82, H-4.90, N-3.48.

Similarly, by adapting the above procedure, the corresponding lithium salts of the compounds of Examples 2-5 can also be prepared.

Example 10 The compounds listed in Table A and Table B hereinbelow were prepared using the appropriate starting materials and the appropriate procedures described in the Examples hereinabove. TABLE A

ELEMENTAL ANALYSIS Melting Carbon Hydrogen Nitrogen Poing No. R R R Calc. Found Calc. Found Calc. Found C 1 H H #** 63.95 64.66 3.76 4.19 4.39 4.78 182-184* 2 CH3 H # 64.86 64.22 4.20 4.65 4.20 3.79 154-155 3 CH3 CH3 # 65.71 65.63 4.61 4.83 4.03 4.12 102-106 4 CH2CH3 H # 65.71 66.55 4.61 5.12 4.03 3.98 143-145 5 CH2CH3 CH2CH3 # 67.20 67.76 5.33 5.63 3.73 3.77 115-120 6 H H 4-F# 60.53 59.66 3.26 3.47 4.15 4.12 136-138 7 CH3 H 2-F# 61.54 61.22 3.70 3.62 3.99 4.45 151-156 8 CH3 CH3 2-F# 62.47 62.95 4.11 4.38 3.84 4.08 91-93 9 CH2CH3 H 2-F# 62.47 60.36 4.11 4.11 3.84 4.02 136-138 10 (CH2)2CH3 H 2-F# 63.32 63.6 4.49 4.7 3.69 3.71 53-60 11 CH2CH3 CH2CH3 2-F# 64.12 63.41 4.83 4.93 3.56 3.85 oil 12 CH3 H 2-Cl# 58.78 58.52 3.54 3.63 3.81 4.05 201-204* * = Decomposition 0** = Phenyl, for example, 2-Cl0 = 2-chlorophenyl TABLE A (cont'd) ELEMENTAL ANALYSIS Melting Carbon Hydrogen Nitrogen Point No. R R R Calc. Found Calc. Found Calc.Found C 13 CH3 CH3 2-Cl# 59.77 59.67 3.93 4.05 3.67 3.72 116-119 14 CH2CH3 H 2-Cl# 59.7 60.5 3.93 4.05 3.67 3.89 131-137 15 CH2CH3 CH2CH3 2-Cl# 61.55 61.72 4.64 4.79 3.42 3.77 113-114 16 H H 2-CH3# 64.86 65.02 4.20 4.43 4.20 4.28 179-181* 17 H H 3-CH3# 64.86 62.54 4.20 4.27 4.20 3.82 148-151 18 H H 4-CH3# 64.86 65.86 4.20 4.25 4.20 4.34 208-211* 19 H H 2-CF3# 55.81 55.58 2.84 3.05 3.62 3.69 68-75 20 H H 3-CF3# 55.81 55.37 2.84 3.09 3.62 3.40 60-63 21 H H 2,6-diF# 57.46 57.45 2.82 3.14 3.94 4.16 225-227* 22 CH3 H 2,6-diF# 58.54 59.3 3.25 3.45 3.79 3.84 191-193* 23 CH2CH3 H 2,6-diF# 59.53 60.11 3.66 4.00 3.66 3.71 63-65 24 -CH2CH=CH2 H 2-F# 63.66 62.4 3.98 4.31 3.71 4.27 oil 25 H H CH3 56.03 56.54 3.89 4.22 5.45 5.52 129-130 26 -CH2C(Cl)=CH2 H # 61.0 57.9 3.8 3.9 3.55 3.2 oil 27 -CH2CH=C(Cl)CH3 H # 61.8 61.3 4.2 4.7 3.4 3.1 134-138 28 -CH(CH3)COOC2H5 H # 63.0 61.5 4.8 5.0 3.3 3.2 oil 29 H -CH3 # 63.74 61.82 3.84 4.9 4.13 3.48 120* 30 H H 1-naphthyl 68.3 65.8 3.8 4.1 3.8 3.8 123-126 31 CH3 H 1-naphthyl 68.9 65.7 4.18 4.4 3.7 3.55 174-179 32 CH3 CH3 1-naphthyl 69.5 69.2 4.5 4.7 3.5 3.6 139-143 0* = Phenyl, for example, 2,6-diF0 = 2,6-difluorophenyl * = Decomposition TABLE A (cont'd) ELEMENTAL ANALYSIS Melting Carbon Hydrogen Nitrogen Point No. R R R Calc. Found Calc. Found Calc.Found C 33 H H H 54.32 54.91 3.29 3.54 5.76 5.42 145-146* 34 CH3 H H 56.03 55.75 3.89 4.04 5.54 5.39 158-159 35 CH3 H CH3 57.56 58.87 4.43 4.66 5.17 5.32 116-118 36 CH2CH3 H CH3 58.95 59.35 4.91 5.04 4.91 5.34 141-142 37 H H CH2CH3 57.56 60.08 4.43 4.91 5.17 5.47 173-174 38 CH3 H CH2CH3 58.95 59.59 4.91 5.12 4.91 5.17 138-139 39 H H (CH2)2CH3 58.95 60.26 4.91 5.19 4.91 5.08 165-168 40 CH3 H (CH2)2CH3 60.20 61.2 5.35 5.84 4.68 4.56 oil 41 CH3 CH3 (CH2)2CH3 61.34 61.82 5.75 6.11 4.47 4.46 oil 42 H H CH(CH3)2 58.95 58.79 4.91 5.23 4.91 5.0 155-156 43 CH3 H (CH(CH3)2 60.20 60.80 5.35 5.36 4.68 4.85 121-122 44 H H (CH2)3CH3 60.20 61.42 5.35 5.68 4.68 4.9 137-138* 45 CH3 H (CH2)3CH3 61.34 62.84 5.75 6.17 4.47 5.03 90 46 CH3 H cyclohexyl 63.72 64.41 5.90 6.18 4.13 3.6 143-145 47 CH2CH3 H cyclohexyl 64.59 64.94 6.23 6.87 3.97 4.11 142-143 * = Decomposition TABLE B

ELEMENTAL ANALYSIS Melting Carbon Hydrogen Nitrogen Point No. R R R Y Calc. Found Calc. Found Calc. Found C 48 H H 2-CH3# Cl 68.11 68.64 4.67 4.97 4.67 4.96 175-177 49 H H 2-F# Cl 63.26 62.3 3.62 3.8 4.61 4.17 178-180* 50 CH3 H 2-Cl# Cl 61.08 62.21 3.87 4.06 4.19 4.33 185-193* 51 CH3 H H Cl 59.07 59.1 4.48 4.95 6.27 6.24 117-120* 52 CH2CH3 H H Cl 60.64 61.11 5.05 5.52 5.90 6.03 177-178 53 H H CH3 Cl 59.07 57.16 4.48 4.5 6.27 5.73 158-159 54 CH3 H CH3 Cl 66.64 62.11 5.05 5.42 5.90 6.05 119-122 55 H H CH2CH3 Cl 60.64 58.69 5.09 5.46 5.89 5.67 152-155 56 CH3 H CH2CH3 Cl 62.03 63.34 5.61 5.83 5.56 5.96 95-97 57 CH3 CH3 CH2CH3 Cl 63.28 62.48 6.07 6.86 5.27 5.93 oil 58 CH2CH2 H CH2CH3 Cl 63.28 63.82 6.7 6.52 5.27 5.89 120-123 59 H H (CH2)2CH3 Cl 62.03 62.13 5.61 5.76 5.56 5.63 152-154 60 CH3 H (CH2)2CH3 Cl 63.28 63.58 6.07 6.49 5.27 5.86 oil * = Decomposition TABLE (cont'd) ELEMENTAL ANALYSIS Melting Carbon Hydrogen Nitrogen Point No. R R R Y Calc. Found Calc. Found Calc. Found C 61 CH2CH3 H (CH2)2CH3 Cl 64.40 65.34 6.49 7.11 5.01 5.33 104-106 62 CH3 CH3 (CH2)2CH3 Cl 64.40 64.14 6.49 6.65 5.01 4.67 oil 63 H H CH2(CH3)2 Cl 62.04 63.69 5.57 6.05 5.57 6.37 156-157 64 CH3 H CH2(CH3)2 Cl 63.29 63.03 6.03 6.72 5.27 5.62 85-91 65 CH2CH3 H CH2(CH3)2 Cl 64.41 65.66 6.44 6.83 5.01 5.47 130-131 66 H H # Br 58.20 54.8 3.64 3.79 4.24 3.97 177-178* 67 CH3 H # Br 59.32 60.79 4.07 4.36 4.07 3.93 181-185 68 CH2CH3 H # Br 60.35 61.01 4.47 4.74 3.91 3.53 161-163 69 H H 2-Cl# Br 52.69 54.59 3.02 3.26 3.84 4.14 202-204 70 CH3 H 2-Cl# Br 53.91 53.77 3.44 3.47 3.70 3.69 205-207 71 CH2CH3 H 2-Cl# Br 55.05 55.3 3.82 3.97 3.57 3.51 144-147 72 H H 2-F# Br 55.19 55.14 3.16 3.57 4.02 3.94 190-191.5 73 CH3 H 2-F# Br 56.37 58.0 3.59 3.41 3.87 4.51 172-173 74 CH2CH3 H 2-F# Br 57.46 57.59 3.99 4.31 3.72 3.57 157-159 75 H H 2-CH3# Br 59.32 58.48 4.07 4.22 4.07 4.03 165-167 76 CH3 H 2-CH3# Br 60.35 60.36 4.47 4.68 3.91 3.96 208-210 77 CH2CH3 H 2-CH3# Br 61.31 62.98 4.84 5.16 3.76 4.24 140-142 78 CH3 H H Br 49.21 48.01 3.73 4.41 5.23 5.06 109-118 79 CH2CH3 H H Br 51.08 50.35 4.26 4.28 4.97 4.86 172-175* 80 H H # CH3 77.0 76.3 5.7 5.9 5.3 5.1 137-141 * = Decomposition TABLE B (cont'd) ELEMENTAL ANALYSIS Melting Carbon Hydrogen Nitrogen Point No. R R R Y Calc. Found Calc. Found Calc.Found C 81 CH3 H # CH3 77.4 77.1 6.1 6.4 5.0 5.1 150-152 82 H H # OCH3 72.6 73.7 5.4 6.6 5.0 5.1 141-144 83 CH3 H # OCH3 73.2 72.5 5.8 5.9 4.7 3.6 128-133 84 CH3 H # OCH(CH3)2 74.30 70.02 6.5 6.47 4.33 4.21 185-188* 85 CH2CH3 H # OCH(CH3)2 74.25 75.88 6.87 7.23 4.15 4.23 111-113 86 H H 2-CH3# OCH(CH3)2 74.28 73.58 6.55 6.85 4.33 4.17 149-155 87 CH3 H 2-CH3# OCH(CH3)2 74.75 74.35 6.81 6.95 4.15 3.83 134-135 88 CH2CH3 H 2-CH3# OCH(CH3)2 75.19 73.63 7.17 7.27 3.99 4.19 134-136 89 H H 2-F# OCH(CH3)2 69.71 70.7 5.54 5.74 4.28 4.25 150-151 90 CH3 H 2-F# OCH(CH3)2 70.37 69.66 5.91 6.1 4.10 4.25 191-193 91 H H 2-Cl# OCH(CH3)2 66.38 68.29 4.07 4.36 5.28 5.48 171-173 92 H H CH3 OCH(CH3)2 68.0 65.75 6.9 6.6 5.7 5.6 151-155 93 CH3 H CH3 OCH(CH3)2 68.97 68.69 7.28 8.01 5.36 6.15 114-115 94 H H # -O# 76.95 76.3 5.0 6.0 4.1 3.0 73-78 95 CH3 H # -O# 77.3 73.9 5.3 5.6 3.9 4.1 163-167 96CH3 CH3 # Y=Cl, X=Cl 62.1 62.9 4.3 4.7 4.0 4.0 133-137 97 -CH2#CH2#2CH2- # -CF3 67.55 72.4 4.85 5.1 3.75 3.8 105-111 96 is 2-phenyl-3-oxo-4-(3,4-dichlorophenyl)-5-dimethylamino-2,3-dihydrofuran * = Decomposition TABLE C COMPARISON COMPOUNDS

(unless otherwise noted X=H and R+=H) ELEMENTAL ANALYSIS Melting Carbon Hydrogen Nitrogen Point No. R R R Y Calc. Found Calc. Found Calc.Found C C-1 CH3 CH3 # H 77.42 75.64 6.09 6.39 5.02 5.03 111-115 C-2 H H H H 68.57 68.99 5.14 5.78 8.0 7.87 221-223* C-3 H H H 3-Cl 57.29 51.6 6.68 5.67 3.82 3.7 214-216* C-4 H H H 4-Cl 57.29 53.46 6.68 5.52 3.82 4.11 169-170* C-5 CH3 H H 4-Cl 59.07 59.34 4.48 5.03 6.27 6.02 133-137* C-6 CH3 CH3 H 4-Cl 60.64 58.61 5.05 5.24 5.90 5.76 161-163 C-7 CH3 H # 4-Cl 68.1 64.4 4.7 5.3 4.7 4.5 oil C-8 H H H 4-CH3 69.84 67.98 5.82 5.63 7.41 6.7 189-191 C-9 CH3 H H 4-CH3 70.94 70.85 6.4 6.63 6.9 6.96 151-156* C-10 H H # 4-CH3 77.0 76.2 5.7 5.9 5.3 5.05 142-146 C-11 CH3 H # 4-CH3 77.4 75.49 6.1 6.14 5.0 4.89 148-154 C-12 H H # 4-OCH3 72.6 70.5 5.4 6.0 5.0 4.8 138-141 C-13 CH3 CH3 # 4-OCH3 73.8 72.9 6.2 6.7 4.5 4.7 140-143 C-14 ** H # 3-CF3 62.7 62.4 3.4 4.5 6.35 5.8 oil C-15 CH3 CH3 R=#, R+=Cl 3-CF3 59.76 57.9 3.93 4.06 3.67 3.56 oil C-16 H H # Y=3-Cl, X=4-Cl 60.0 60.1 3.5 3.7 4.4 4.8 179-182 C-16 is 2-phenyl-3-oxo-4-(3,4-dichlorophenyl)-5-amino-2,3-dihydrofuran * = Decomposition ** = 4-NO20 Example 11 In this example, the compounds of Table A and Table B were respectively tested using the procedures described hereinbelow for pre-emergent and post-emergent activity against a variety of grasses and broad-leaf plants including one grain crop and one broad-leaf crop. The compounds tested are identified by compound number in Table A or Table B hereinabove.

Pre-emergent herbicide test Pre-emergence herbicidal activity was determined in the following manner.

Test solutions of the respective compounds were prepared as follows: 355.5 mg of test compound was dissolved in 15 ml of acetone. 2 ml of acetone containing 110 mg of a nonionic surfactant was added to the solution. 12 ml of this stock solution was then added to 47.7 ml of water which contained the same nonionic surfactant at a concentration of 625 mg/l.

Seeds of the test vegetation were planted in a pot of soil and the test solution was sprayed uniformly onto the soil surface either at a dose of 27.5 micrograms/cm2 or in some instances as indicated in Table 1 hereinbelow, certain of the compounds were tested at a lower dosage of 15.6 micrograms/cm2. The pot was watered and placed in a greenhouse. The pot was watered intermittently and observed for seedling emergence, health of emerging seedlings, etc., for a 3-week period. At the end of this period, the herbicidal effectiveness of the compound was rated based on the physiological observations. A 0-to-100 scale was used, 0 representing no phytotoxicity, 100 representing complete kill. The results of these tests are summarized in Table 1.

Post-emergent herbicidal test The test compound was formulated in the same manner as described above for the pre-emergent test.

This formulation was uniformly sprayed on 2 similar pots containing plants 2 to 3 inches tall (except wild oats, soybean and watergrass which were 3 to 4 inches tall) (approximately 15 to 25 plants per pot) at a dose of 27.5 microgram/cm2. After the plants had dried, they were placed in a greenhouse and then watered intermittently at their bases as needed. The plants were observed periodically for phytotoxic effects and physiological and morphological responses to the treatment. After 3 weeks, the herbicidal effectiveness of the compound was rated based on these observations. A 0-to-100 scale was used, 0 representing no phytotoxicity, 100 representing complete kill. The results of these tests are summarized in Table 2.

TABLE 1 Pre-emergence herbicidal activity Application Rate: 27.5 micrograms/cm, unless otherwise noted Broad-Leaf Plants Grasses Compound % Phytotoxicity % Phytotoxicity No. Lambsquarter Mustard Pigweed Soybean Crabgrass Watergrass Wild Oats Rice 1 94 100 100 95 100 100 100 93 2 100 100 100 100 100 100 100 100 3a 98 100 100 60 100 80 100 60 4a 95 100 100 98 100 100 100 75 5 100 80 100 20 100 70 100 20 6 100 100 100 85 100 100 100 85 7a 100 100 100 100 100 100 100 100 8a 98 100 100 100 100 100 100 70 9a 100 100 100 100 100 100 100 100 10 100 100 100 90 100 100 100 90 11a 90 50 100 60 100 50 60 20 12a 100 100 100 90 100 100 100 95 13a 100 100 100 100 100 100 100 95 14a 100 100 100 70 100 100 100 95 15a 95 90 100 20 100 50 70 0 16 100 100 100 85 100 100 100 95 17 99 83 98 55 100 70 63 55 18 0 0 0 0 0 0 0 19a 100 80 100 20 98 100 100 90 20 100 100 100 75 98 65 85 50 21 95 90 25 40 100 100 100 80 22 100 100 100 100 100 100 100 100 23 100 100 100 70 100 100 100 95 24a 98 90 100 65 100 95 70 55 25 90 85 85 90 100 88 80 65 26 95 75 100 30 0 95 0 230 a = Tested at 15.6 micrograms/cm TABLE 1 (cont'd) Broad-Leaf Plants Grasses Compound % Phytotoxicity % Phytotoxicity No.Lambsquarter Mustard Pigweed Soybean Crabgrass Watergrass Wild Oats Rice 27 0 0 0 0 0 0 0 0 28 99 98 100 45 99 48 67 45 29 98 97 100 98 100 100 90 100 30 98 55 100 25 78 55 55 15 31 100 100 100 80 100 100 95 80 32 95 80 100 25 100 80 60 75 33 95 100 70 78 98 80 90 78 34 100 100 100 100 100 100 100 100 35 100 100 100 100 100 100 100 100 36 100 100 100 100 100 100 100 100 37 100 100 100 85 98 85 98 70 38 100 100 100 100 100 100 100 100 39 100 100 100 70 100 100 100 88 40 100 100 100 100 100 100 100 100 41 100 100 100 50 100 100 100 65 42 95 100 100 25 35 88 10 0 43 100 100 100 100 100 100 100 100 44 90 100 100 15 98 99 75 10 45 100 100 100 93 100 100 100 100 46 100 100 100 70 100 100 90 70 47 100 55 60 30 100 95 70 48 60 65 30 75 25 25 25 93 49 100 100 100 100 100 100 100 100 50 100 100 100 100 100 100 100 100 51 100 100 100 98 100 100 100 95 52 100 100 100 100 100 100 100 100 53 60 65 50 35 0 15 0 0 54 100 100 100 93 100 100 100 97 55 55 50 0 25 73 20 0 0 56 100 100 100 100 100 100 100 80 57 98 100 100 45 100 65 30 40 58 100 100 75 90 100 100 85 90 59 50 45 0 0 60 15 0 0 60 100 100 100 99 100 100 100 97 61 100 100 85 93 100 100 80 93 62 100 100 100 45 100 94 50 30 63 25 45 0 0 20 20 0 0 64 98 100 100 93 100 100 95 60 TABLE 1 (cont'd) Broad-Leaf Plants Grasses Compound % Phytotoxicity % Phytotoxicity No.Lambsquarter Mustard Pigweed Soybean Crabgrass Watergrass Wild Oats Rice 65 100 100 100 90 100 100 100 85 66 100 100 100 70 100 95 98 90 67 100 100 100 100 100 100 100 100 68 100 100 100 100 100 100 100 100 69 100 98 99 75 100 100 99 85 70 100 95 90 90 100 100 100 95 71 100 95 97 70 100 100 95 93 72 100 100 99 85 100 100 100 99 73 100 100 100 100 100 100 93 100 74 100 100 80 93 100 100 98 97 75 100 99 100 50 100 100 98 95 76 100 93 85 90 100 100 99 93 77 100 99 98 85 100 100 94 93 78 100 98 70 90 100 100 100 98 79 100 100 100 100 100 100 100 100 80 25 20 0 0 95 25 10 0 81 100 100 100 100 100 100 100 0 82 80 55 20 45 98 25 20 0 83 100 100 100 70 100 100 100 0 84 99 95 100 98 100 100 100 97 85 100 97 100 97 100 100 99 97 86 100 100 100 85 100 100 90 75 87 100 95 100 95 99 100 98 80 88 100 100 100 90 100 100 98 90 89 100 100 100 99 100 100 100 100 90 100 100 100 100 100 100 99 99 91 99 100 100 97 100 100 95 97 92 20 20 0 25 0 0 0 0 93 100 100 100 100 100 100 100 93 94 75 55 98 0 90 30 0 0 95 100 100 100 55 100 100 75 40 96 93 50 100 0 100 60 30 0 97 100 100 100 70 100 100 99 80 TABLE 1A COMPARISON COMPOUNDS Pre-emergence Herbicidal Activity Application Rate: 27.5 micrograms/cm, unless otherwise noted Borad-Leaf Plants Grasses Compound %Phytotoxicity % Phytotoxicity No.Lambsquarter Mustard Pigweed Soybean Crabgrass Watergrass Wild Oats Rice C-1 40 25 40 0 75 0 0 0 C-2 0 0 0 0 0 0 0 0 C-3 0 0 0 0 0 0 0 0 C-4 0 0 0 0 0 0 0 0 C-5 0 0 0 0 0 0 0 0 C-6 0 0 0 0 0 0 0 0 C-7 0 0 0 0 0 0 0 0 C-8 30 25 0 40 0 0 0 0 C-9 0 0 0 0 0 0 0 0 C-10 0 0 0 0 0 0 0 0 C-11 0 0 0 0 30 0 0 0 C-12 0 0 0 0 0 0 0 0 C-13 0 0 0 0 0 0 0 0 C-14 0 0 0 0 45 35 0 0 C-15 0 0 0 0 0 0 0 0 C-16 0 0 0 0 0 0 0 0 TABLE 2 Post-Emergence Herbicidal Activity Application Rate: 27.5 micrograms/cm, unless otherwise noted Broad-Leaf Plants Grasses Compound % Phytotoxicity % Phytotoxicity No.Lambsquarter Mustard Pigweed Soybean Crabgrass Watergrass Wild Oats Rice 1 60 100 50 50 40 33 45 20 2 85 100 92 90 58 60 60 42 3a 70 90 75 65 0 0 0 0 4a 60 95 75 80 50 65 65 45 5 80 90 70 60 30 30 30 0 6 60 80 60 40 45 60 60 20 7a 95 100 98 100 80 80 90 80 8a 65 100 65 80 40 65 65 20 9a 80 95 90 90 70 90 90 60 10 90 100 90 80 30 0 30 0 11a 90 90 90 80 30 20 20 20 12a 100 100 90 90 90 40 50 20 13a 90 100 90 90 30 50 0 0 14a 80 90 90 70 50 80 90 40 15a 80 90 80 70 20 0 0 0 16 65 95 60 55 70 80 75 20 17 35 73 35 30 0 0 0 0 18 0 0 0 0 0 0 0 0 19a 55 45 45 0 55 45 40 0 20 43 80 45 33 0 0 0 0 21 50 30 60 50 30 0 0 0 22 80 80 70 70 60 90 70 0 23 85 100 90 80 70 100 60 30 24a 85 80 75 65 40 35 0 0 25 25 50 N.T.* 50 0 0 0 0 N.T.* = Not Tested a = Tested at 15.6 micrograms/cm TABLE 2 (cont'd) Broad-Leaf Plants Grasses Compound % Phytotoxicity % Phytotoxicity No. Lambsquarter Mustard Pigweed Soybean Crabgrass Watergrass Wild Oats Rice 26 40 55 60 45 0 0 0 0 27 50 30 35 0 0 0 0 0 28 35 40 0 0 0 0 0 0 29 75 100 100 80 70 85 65 52 30 30 45 45 45 10 30 20 0 31 70 80 80 70 30 40 20 0 32 40 40 35 35 0 0 0 0 33 70 65 42 50 35 40 60 45 34 85 100 85 85 80 92 89 60 35 100 100 100 100 100 90 98 75 36 75 98 70 70 65 80 65 35 37 50 50 45 40 0 0 0 0 38 85 100 100 70 75 75 75 65 39 47 60 40 0 0 0 0 0 40 95 100 98 80 95 95 95 95 41 90 100 90 90 45 75 75 30 42 11 0 10 25 0 0 0 0 43 80 100 75 95 90 80 90 45 44 25 25 25 20 0 0 0 0 45 75 95 90 90 55 75 65 0 46 50 90 50 40 20 25 0 0 47 70 70 70 85 40 30 35 15 48 60 65 30 30 25 25 25 0 49 75 90 80 40 60 60 30 75 50 85 90 90 65 80 85 80 55 51 50 50 40 60 30 25 25 0 52 95 100 95 85 60 60 75 25 53 30 15 0 33 0 0 0 0 TABLE 2 (cont'd) Broad-Leaf Plants Grasses Compound % Phytotoxicity % Phytotoxicity No. Lambsquarter Mustard Pigweed Soybean Crabgrass Watergrass Wild Oats Rice 54 60 87 75 73 35 40 0 0 55 0 0 0 0 0 0 0 0 56 55 93 70 90 0 0 0 0 57 30 45 85 70 0 0 0 0 58 45 50 30 65 0 0 0 0 59 0 0 0 0 0 0 0 0 60 75 98 80 80 20 20 0 0 61 75 85 80 90 30 25 10 10 62 45 60 60 70 0 0 30 0 63 0 0 0 0 0 0 0 0 64 70 80 65 75 0 0 0 0 65 55 60 40 55 0 0 0 0 66 50 65 50 45 0 0 0 0 67 95 100 95 95 93 90 90 70 68 93 98 85 75 75 70 75 20 69 75 93 75 70 0 0 0 0 70 95 95 90 85 25 20 20 10 71 80 93 55 80 25 20 10 10 72 45 93 50 30 30 35 35 20 73 93 100 70 93 30 55 45 25 74 N.T.* N.T.* - - - - - 75 65 75 70 55 25 30 30 20 76 90 85 85 80 25 20 20 0 77 85 100 90 75 25 20 20 20 78 90 98 85 75 20 20 20 0 N.T.* = Not Tested TABLE 2 (cont'd) Broad-Leaf Plants Grasses Compound %Phytotoxicity %Phytotoxicity No. Lambsquarter Mustard Pigweed Soybean Crabgrass Watergrass Wild Oats Rice 79 90 60 80 93 60 70 70 25 80 0 20 0 20 0 0 0 0 81 70 98 85 80 35 65 65 25 82 20 25 35 30 0 0 0 0 83 75 100 75 85 35 20 55 0 84 60 30 45 40 63 55 40 30 85 75 40 45 90 45 45 35 0 86 40 65 35 30 0 0 0 0 87 90 90 90 90 65 70 70 25 88 80 65 55 85 20 20 10 10 89 85 98 90 88 0 65 90 0 90 85 70 50 83 55 65 70 30 91 83 98 85 75 25 60 78 10 92 0 0 0 0 0 0 0 0 93 70 80 65 80 30 35 25 0 94 25 20 20 20 0 0 0 0 95 65 65 65 40 25 20 0 0 96 65 70 70 55 0 0 0 0 97 70 80 65 55 0 0 0 0 TABLE 2A COMPARISON COMPOUNDS Post-Emergence Herbicidal Activity Application Rate: 27.5 micrograms/cm, unless otherwise noted Broad-Leaf Plants Grasses Compound % Phytotoxicity % Phytotoxicity No.Lambsquarter Mustard Pigweed Soybean Crabgrass Watergrass Wild Oats Rice C-1 20 20 0 25 0 0 0 0 C-2 0 0 0 0 0 0 0 0 C-3 0 0 0 0 0 0 0 0 C-4 0 0 0 0 0 0 0 0 C-5 0 0 0 0 0 0 0 0 C-6 0 0 0 0 0 0 0 0 C-7 0 0 0 0 0 0 0 0 C-8 25 20 25 30 0 0 0 0 C-9 20 20 10 25 0 0 0 0 C-10 0 0 0 0 0 0 0 0 C-11 20 0 0 20 0 0 0 0 C-12 0 0 0 0 0 0 0 0 C-13 0 0 0 0 0 0 0 0 C-14 0 0 0 0 0 0 0 0 C-15 25 25 0 30 25 10 45 45 C-16 0 0 0 0 0 0 0 0 As can be seen from the above Table 1, the compounds of the invention generally exhibit a broad spectrum of excellent pre-emergence phytotoxic activity and especially so Compounds Nos. 2,4,7, 9, 12, 14, 16, 22. Moreover, as shown by Table 2 the compounds also generally exhibit post-emergence phytotoxic activity against broad-leaf plants and in some instances also against grasses, especially so Compound Nos.

7, 9, 12, 14, 16, 22 and 23. Also, it can be seen that the corresponding Comparison Compounds had much poorer activity than the corresponding compounds of the present invention.

Claims

1. Compounds represented by the general formula:

wherein R is lower alkyl, cycloalkyl having 3 to 7 carbon atoms; lower alkenyl; haloalkyl having 1 to 4 carbon atoms and 1 to 3 halo atoms independently selected from fluoro, chloro, bromo and iodo; haloalkenyl having 2 to 4 carbon atoms and 1 to 3 halo atoms independently selected from fluoro, chloro, bromo and iodo; lower alkoxy; lower alkylthio; lower alkoxyalkyl wherein the alkyl and alkoxy moieties independently have 1 to 3 carbon atoms; alkylthioalkyl wherein the alkyl moities independently have 1 to 3 carbon atoms; phenyl, naphth-1-yI; inden-1-yI; 4-fluorophenyl; arylalkylene having 1 to 3 carbon atoms in the alkylene moiety and wherein the aryl moiety is phenyl, naphth-1-yl or inden-1-yI; or R is a substituted aryl or substituted arylalkylene selected from:

wherein one, two or three of R4, R5, R6, R7, R8, and R9 are independently selected from lower alkyl, lower alkoxy, halo, nitro, or haloalkyl having 1 to 3 carbon atoms and 1 to 3 of the same or different halo atoms, and the remainder are hydrogen; and R3 is a single bond or alkylene having 1 to 3 carbon atoms; R1 is hydrogen or alkyl having 1 to 4 carbon atoms;R2 is hydrogen, alkyl having 1 to 4 carbon atoms, alkenyl having 3 or 4 carbon atoms, lower alkoxycarbonylalkyl, lower alkoxyalkyl or lower alkylthioalkyl; or R1 and R2 together with the nitrogen atom to which they are joined form a saturated or unsaturated nitrogen heterocycle having 3 to 6 carbon atoms of which one is nitrogen and the remainder are carbon atoms; X is hydrogen, lower alkyl, lower alkoxy, halo or trifluoromethyl and can be at any available position on the phenyl ring; and Y is lower alkyl, lower alkoxy, halo, lower haloalkyl having 1 to 4 carbon atoms and 1 to 3 of the same or different halo atoms, lower haloalkoxy having 1 to 4 carbon atoms and 1 to 3 of the same or different halo atoms, or lower haloalkylthio having 1 to 4 carbon atoms and 1 to 3 of the same or different halo atoms, with the proviso that when Y is halo then R, R1 and R2 are not all hydrogen and the further proviso that when Y is other than trifluoromethyl and X is other than hydrogen, and R1 and R2 are each hydrogen, then R is methyl, ethyl, propyl, 2-halophenyl, 2-lower alkylphenyl or 4-fluorophenyl; and compatible salts thereof.

2. Compounds as claimed in Claim 1, wherein R1 and R2 are independently hydrogen, methyl, ethyl or propyl.

3. Compounds of as claimed in Claim 2, wherein one of R1 and R2 is hydrogen and the other is hydrogen, methyl, ethyl or propyl.

4. Compounds as claimed in Claim 2, wherein one or R1 and R2 is hydrogen and the other is hydrogen, methyl or ethyl.

5. Compounds as claimed in Claim 1,2,3 or 4, wherein Xis hydrogen.

6. Compounds as claimed in any preceding claim, wherein R is phenyl, naphth-l-yl, 4-fluorophenyl or substituted aryl.

7. Compounds as claimed in Claim 6, wherein R is phenyl, naphthyl or a monosubstituted phenyl.

8. Compounds as claimed in Claim 7, wherein R is phenyl, halophenyl, or lower alkylphenyl.

9. Compounds as claimed in Claim 8, wherein R is phenyl, 44luorophenyl, 2-halophenyl, or 2-lower alkylphenyl.

10. Compounds as claimed in Claim 9, wherein Xis hydrogen and R1 and R2 are independently hydrogen, methyl or ethyl.

11. Compounds as claimed in any one of Claims 1 to 5, wherein R is lower alkyl, cycloalkyl, lower alkenyl, haloalkyl or haloalkenyl.

12. Compounds as claimed in Claim 11, wherein R is methyl, ethyl or propyl.

13. Compounds as claimed in Claim 12, wherein one of F1 or R2 is hydrogen and the other is methyl or ethyl.

14. Compounds as claimed in any preceding claim, wherein Y is halo ortrifluoromethyl.

15. Compounds as claimed in any one of Claims 1 to 13, wherein Y is trifluoromethyl.

16. 2-(2-Fluorophenyl)-3-oxo-4-(3-trif luoromethyl phenyl)-5-methylamino-2,3-dihydrofuran.

17. 2-(2-Fluorophenyl)-3-oxo-4-(3-trifluoromethylphenyl)-5-ethylamino-2,3-dihydrofuran.

18. 2-(2-Chlorophenyl)-3-oxo-4-(3-trif luoromethyl phenyl)-5-methylamino-2,3-dihydrofuran.

19. 2-(2-Chlorophenyl)-3-oxo-4-(3-trifluoromethylphenyl)-5-ethylamino-2,3-dihydrofuran.

20. 2-(2-Methylphenyl)-3-oxo-4-(3-trifluoromethylphenyl )-5-amino-2,3-dihydrofuran.

21. 2-(2',6'-Difluorophenyl)-3-oxo-4-(3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran.

22. A herbicidal composition comprising a herbicidally effective amount of a compound as claimed in Claim 1 and a compatible carriertherefor.

23. A herbicidal composition comprising a herbicidally effective amount of a compound as claimed in any one of Claims 2 to 21 and a compatible carrier therefor.

24. A method of preventing or destroying plants which comprises applying a herbicidally effective amount of a compound as claimed in Claim 1, to the foliage or potential growth medium of said plants.

25. A method of preventing or destroying plants which comprises applying a herbicidally effective amount of a compound as claimed in any one of Claims 2 to 21 to the foliage or potentiai growth medium of said plants.

26. A plant growth regulating composition which comprises a compound as claimed in Claim 1 in an amount effective to alter the growth pattern of plants, in association with a compatible carrier therefor.

27. A method of regulating the growth of plants which comprises applying to the foliage of said plants or their growth medium a compound as claimed in Claim 1 in an amount effective to alter the growth pattern of such plants.

28. A method of preparing a compound as claimed in Claim 1 wherein R is phenyl, naphth-1-yl, inden-1-yl our a substituted aryl as defined in Claim 1,which comprises the step of contacting a compound having the general formula:

wherein X and Y are as defined in Claim 1 and Z' corresponds to the desired R aryl or substituted aryl substituent, with a halogen selected from chlorine, bromine and iodine and a liquid carboxylic acid under reactive conditions such as to thereby produce the desired compound.

29. A method according to Claim 28, wherein said method is conducted in an inert organic solvent at temperatures in the range from 0 to 1 00"C and said halogen is bromine.

30. A method according to Claim 29, wherein excess liquid carboxylic acid is used as inert organic solvent.

31. A method of preparing a compound as claimed in Claim 1, substantially as described in any one of the foregoing Examples 2,3,6,7,8,9 and 10.