FR2547581A1 - 5-AMINO-3-OXO-4- (SUBSTITUTED PHENYL) -2,3-DIHYDROFURAN AND ITS DERIVATIVES, PROCESS FOR THEIR PREPARATION AND THEIR APPLICATIONS AS HERBICIDES AND PLANT GROWTH SUBSTANCES - Google Patents

Abstract

THE INVENTION IS IN THE FIELD OF PESTICIDES. IT CONCERNS A NEW COMPOUND OF FORMULA: (CF DRAWING IN BOPI) WHICH ARE 5-AMINO-3-OXO-4- (PHENYL SUBSTITUTE) -2,3-DI-HYDROFURANS AND THEIR DERIVATIVES. IT ALSO CONCERNS A PROCESS FOR PREPARING THESE COMPOUNDS. THE COMPOUNDS OF THE INVENTION ARE GENERALLY PHYTOTOXICITY BOTH PRE-EMERGENCY AND POST-EMERGENCY AND ARE USEFUL AS HERBICIDES AND ALSO, IN SINGLE DOSES, AS SUBSTANCES INFLUENCING PLANT GROWTH.

Description

The present invention relates to 5-amino3-oxo-4- (substituted phenyl) -2,3-

  dihydrofurans and their derivatives, and the use of these compounds as herbicides

  and as plant growth substances.

  The article published in Chemiker-Zeitung 104 (1980) No. 10, pages 302-303, is an academic article revealing the cyclization of 1- (dimethylamino) 2,4-diphenyl-1-butene-3,4-dione to form the 5-Dimethylamino-2,4-diphenyl-2,3-dihydrofuran British Patent No. 1,521,092 discloses certain 3-phenyl-4- (1H) pyrid-ones or -thiones substituted in the 5-position as herbicidal compounds. Japanese Patent No. 13,710 / 69 (Chemical Abstracts 71: 61195e) discloses the general formula of an amino-3-oxo-4- (phenyl and halo-phenyl) -2,3-dihydrofuran and discloses in particular the 5- amino-3-oxo-4- (phenyl and 4-chlorophenyl) -2,3-dihydrofurans Japanese Patent No. 19,090 (Chemical Abstracts 69 P 10352 e) discloses certain 2,3dihydrothiophene Helvetica Chemica Acta as pharmaceutical substances, Volume 66, pages 362-378 (1983) discloses 5-N-cyclopropyl-4-phenyl-2-methoxycarbonylmethylene-3-furanone as

  part of an academic debate on chemical synthesis.

  U.S. Patent No. 4,441,910 discloses

  ureidosulfonylfurans and herbicidal ureidosulfonylthiophenes.

  The present invention provides compounds having both pre-emergence and post-emergence herbicidal activity and having very good pre-emergence activity against a broad spectrum of broadleaf weeds and weeds of the gramineae family. At lower application rates, the compounds also exhibit properties as plant growth substances. The compounds of the present invention may be represented by the following formula: x y / g o

Y

R 2 II

  Wherein R is a lower alkyl radical 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 halogen atoms independently selected from the group consisting of fluoro, chloro, bromo or iodo; a haloalkyl radical having 2 to 4 carbon atoms and 1 to 3 halogen atoms independently selected from the group of fluoro, chloro, bromo or iodo radicals; a lower alkoxy radical; lower alkylthio; lower alkoxyalkyl wherein the alkoxy and alkyl moieties independently have 1 to 3 carbon atoms; a lower alkylthioalkyl radical whose alkyl portions have independently 1 to 3 carbon atoms; a phenyl, naphth-1-yl, inden-1-yl radical; 4-fluorophenyl; an arylalkylene radical having 1 to 3 carbon atoms in the alkylene portion and wherein said aryl portion is a phenyl, naphth-1-yl or inden-1-yl radical; or an aryl or substituted aralkylene radical selected from the group of formulas:

R 4 R 5 R 4 R 5

- (R 3); (R 3) 4

7 R 6 R O 6; or R 9 R 6; or

R 8% R 7

R 4 R 5

R

- (R 3)

XR 6;

R 8 R 7

4 5 6 7 _ 8 9

  one, two or three of R 4 R 5, R 6, R 7, R and R are independently selected from the group consisting of lower alkyl, lower alkoxy, halogen, nitro or halogenalkyl having 1 to 3 carbon atoms; and 1 to 3 equal or different halogen atoms, and the others are hydrogen; and R 3 is a single bond or an alkylene radical having 1 to 3 carbon atoms; R 1 represents hydrogen or an alkyl radical having 1 to 4 carbon atoms; R 2 is hydrogen, an alkyl radical having 1 to 4 carbon atoms, alkenyl having 3 or 4 carbon atoms, alkoxycarbonylalkyl having 1 to 4 carbon atoms in the alkoxy moiety and 1 to 4 carbon atoms in the alkyl moiety alkoxyalkyl wherein the alkoxy and alkyl moieties have, independently, 1 to 3 carbon atoms, or alkylthioalkyl wherein the alkyl moieties independently have 1 to 3 carbon atoms; or R and R together with the nitrogen atom to which they are attached form a saturated or unsaturated nitrogenous heterocycle having 3 to 5 atoms in the ring, one of which is a nitrogen atom and the others are carbon X represents hydrogen, lower alkyl, lower alkoxy, halo or trifluoromethyl and may be in any of the available positions on the phenyl ring; and Y is lower alkyl, lower alkoxy, halo, lower haloalkyl having 1 to 4 carbon atoms and 1 to 3 equal or different halogen atoms; the lower haloalkoxy radical having 1 to 4 carbon atoms and 1 to 3 equal or different halogen atoms; or a lower haloalkylthio radical having 1 to 4 carbon atoms and 1 to 3 equal or different halogen atoms; with the proviso that when Y is a halogeno radical, R, R 1 and R 2 are not all hydrogen and, furthermore, provided that when Y is other than a trifluoromethyl radical and X is something other than that hydrogen, and R is hydrogen and R is hydrogen, R is then methyl, ethyl, propyl, 2-halophenyl,

  2- (lower alkyl) -phenyl or 4-fluorophenyl.

  The invention also relates to compatible salts of the compound of formula (I), for example salts obtained by replacement of the amine hydrogen (that is to say, R 1 and R 2 represent hydrogen) by a compatible cation or

  by enolating the 3-oxo group after replacement of the amine hydro gene.

  The compounds of formula (I) exist in the form of keto-isomers. The compounds also have an asymmetric carbon atom and may also exist in the form of optical isomers. In some cases, the compounds also exist in the form of geometric isomers The above formula is intended to cover the respective individual isomers as well as their mixtures, and the respective isomers and mixtures thereof all fall within

the scope of the invention.

  It has also been found that the presence of a 3-trifluoromethyl substituent on the 4-phenyl group of the compounds of the present invention generally favors

  to a very appreciable extent the herbicidal activity.

  According to another of its aspects, the invention provides a herbicidal composition comprising a compatible carrier and a herbicidally effective amount of the compounds of formula (I), or compatible salts thereof,

or their mixtures.

  The present invention also provides a method for preventing or combating the development of a

  undesirable vegetation, which consists in treating the growth medium and / or the foliage of this vegetation with a herbicidally effective amount of the compound (s) of formula (I) and / or their compatible salts.

  According to another of its aspects, the present invention provides a composition influencing plant growth, comprising a compatible carrier and a quantity influencing the growth of plants, the compound of formula (I), compatible salts thereof, or their

  mixtures, effective for modifying the normal pattern of growth of said plants.

  The present invention also provides a method of influencing plant growth which comprises treating the growth medium and / or foliage of said vegetation with an amount effective to influence plant growth of the compound (s) of formula (I)

  and / or its modifiable salts, in order to modify 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 is described in detail in the following.

  Illustrative compounds of the formula (I) of the present invention will be given in Examples 2, 3 and 6. From the point of view of the substituents, the compounds which are preferred are those in which R is an alkyl radical. lower, aryl or substituted aryl, especially methyl, ethyl, propyl, phenyl or substituted phenyl, and in particular phenyl, monomethylphenyl or monohalophenyl, especially methyl, ethyl, n-propyl, 2-halophenyl, 2- (lower alkyl) phenyl or 4- fluoro phenyl; R 1 and R 2 represent, independently, hydrogen, a methyl, ethyl or n-propyl radical, more particularly one of R 1 and R is hydrogen and the other represents hydrogen or the methyl radical, ethyl or n-propyl, preferably hydrogen, the methyl radical or the ethyl radical and in particular the methyl radical; X is hydrogen and / or Y is a trifluoromethyl or 3halogeno radical, especially 3-trifluoromethyl. The most preferred compounds contain a combination of two or

  more than two recommended substituents.

  Compounds of formula (I) wherein R and R 2 are each hydrogen and R is aryl or substituted aryl may be conveniently prepared according to the following reaction scheme: X A, O

Y CHCCH 2 Z '

I CN (A) X> o _> y O 2 1

H 2 N O Z '

  (I ') wherein X and Y have the definitions given above;

  and Z 'is an aryl or substituted aryl radical.

  Transposition of the compound (A) to the compound (I ') can be carried out conveniently by contacting the

  compound (A) with a halogen, preferably bromine, and a liquid carboxylic acid in the presence of an inert organic solvent.

  Normally, this process is carried out at temperatures in the range of about 0 to 100 ° C, preferably about 20 to 30 ° C for about 4 to 36 hours, preferably about 18 to 24 hours, using about 1.0 to 10.0, preferably 1.0 to 1.1 moles of halogen per mole of compound (A). Liquid carboxylic acids which can be advantageously used include, for example, acetic acid. propionic acid, butyric acid, formic acid, etc. When an excess of carboxylic acid is used, the excess may serve as a solvent or liquid carrier for this reaction system. Other organic solvents which can be used include, for example, liquid halogenated alkanes such as methylene chloride, carbon tetrachloride, chloroform, 1,2-dichloroethane; liquid aromatic hydrocarbons, for example benzene, toluene; liquid alkyl ethers, for example

  diethyl ether, dimethylsulfoxide, dimethylformamide, etc., and their compatible mixtures.

  We get the best results using

  bromine as halogen, although chlorine and iodine can also be used.

  The starting materials of formula (A) can be prepared according to the following reaction scheme:

(> CH 2 CN + Z'-CH 2-C-OR 1 -> (A)

yz

(B) '' (C)

  in which R 1 is a lower alkyl radical, aryl

  (for example phenyl) or arylalkylene (for example benzyl); and Z ', Y and X have the definitions given above.

  This process can be conveniently carried out by contacting the compound (B) with the compound (C) and a strong base, preferably in an inert organic solvent. Normally, this process is carried out at temperatures in the range of about 0 to 100 ° C, preferably 75 to 85 ° C for about 5 to 36 hours, preferably 18 to 24 hours using about 0 to 10.0, preferably 1.0 to 1.2 moles of compound (C) per mole of compound (B).

  uses about 1.0 to 10.0 moles of base per mole of settled compound (C).

  Suitable strong bases which may be used include, for example, alkali metal alkanolates such as sodium methoxide, sodium ethoxide, potassium ethoxide, sodium hydride,

  potassium hydride, etc. The strong base should preferably be a base which does not form water as produced in this reaction system.

  Suitable inert solvents which can be used include, for example, lower alkanols (such as methanol, ethanol and propanol), tetrahydrofuran, dimethoxyethane, dioxane, etc., and their compatible mixtures. Alkanolate The alkali metal is advantageously prepared in situ by reaction of an alkali metal with an excess alkanol which in turn serves as the alkali metal.

  solvent for the above reaction.

  The starting materials of formulas (B) and (C) are generally known materials and can be prepared by known methods or by obvious variants of these processes (i.e. by substitution of suitable starting materials The preparation of the compound (B) is described, for example in Org Syn Coll, vol. 1, 107 (1941) and the preparation of the compound (C) is

  described in Org Syn Coll, Vol. 1, 270 (1941).

  The compounds of formula (I) in which R 1 and R 2 each represent hydrogen may be prepared by the general process schematized by the following overall reaction equation X

H C + RC-O 5 ==.

2 RCN + RC-C-R 5> R 5 OH

y 31 H 2 N R y

(B) (E) (1,)

  in which R, X and Y have the definitions given above; and R 5 is a lower alkyl, aryl (by

  phenyl example) or arylakylene (for example benzyl).

  This process may advantageously be carried out by contacting the compound (B) with the compound (E) and a strong base (for example sodium methoxide, ethylate

  sodium), especially in an inert organic solvent.

  Normally, this process is carried out at temperatures in the range of about 0 to C, preferably 75 to 85 ° C for about 5 to 36 hours, preferably 18 to 24 hours, using about 1.0. at 10.0, preferably 1.0 to 1.2 moles of compound (E) per mole of compound (B) Inert organic solvents which can be used advantageously include, for example, lower alkanols (for example methanol,

  ethanol, propanol, etc); tetrahydrofuran; dimethoxyethane; dioxane; etc., and their compatible mixtures.

  Bases that can be advantageously used for this process include the bases that have already been mentioned about the reaction of the compound (B) with the

compound (C).

  The hydroxyesters of formula (E) are generally known compounds and can be prepared by known procedures or by obvious modifications of these procedures (for example by using

  suitably substituted starting materials).

  Compounds of formula I wherein R 1 and R 2 are hydrogen and R is alkyl, cycloalkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, arylalkylene, substituted arylalkylene or alkenylalkyl (eg -CH 2 CH = CH) may also be conveniently prepared. By the following process: x O <(CHC-CHR '' '+ cyclizing agent> I il

CN OR 10

Y (A ') X y

H 2 N O R '' '

(I "')

  in which R '' 'is an alkyl, cycloalkyl, alkoxyalkyl, alkoxy, alkylthioalkyl, arylalkylene, arylalkylene radical

  substituted or alkenyl and R 10 is a lower alkyl radical, preferably methyl.

  This process can advantageously be carried out by contacting the compound (A ') with a cyclizing agent under reactive conditions, preferably in a

inert organic solvent.

  Normally, this process is carried out at temperatures in the range of about 0 to about C, preferably about 115 to 120 C for about 10 to 120 minutes, preferably about 10 to 30 minutes, using about 1 to 10, preferably 1 to 2 moles of cyclizing agent per mole of the compound (A ') Suitable cyclizing agents which can be used include, for example, strong anhydrous acids such as sulfuric acid, hydrogen chloride, hydrogen bromide, trifluoroacetic acid, methanesulfonic acid, etc. The best results are normally obtained using anhydrous sulfuric acid. Suitable inert organic solvents which can be used include, for example, acetic acid, propionic acid, butyric acid, toluene,

  xylene, etc. and their compatible mixtures.

  The starting materials of formula (A ') can be prepared according to the process schematized hereinafter

X X

o CHCH 2 O Rt O> C C-CH 20 R'0

I (1> I

/ CN / c No.

Y

(B ') (B ")

X

  o r 8 EM + C c CH o OR 1 R '"' X '(A) CN Y

(B '' ')

  wherein R '' 'and R 10 are as defined above; X 'is a chloro, bromo or iodo radical and M and M' independently represent sodium or lithium. Although this process is schematically represented as a three-step process, the steps are normally and conveniently conducted in situ. As is also conventional with such reactions, the reactions are preferably conducted in substantially anhydrous conditions in a gas atmosphere. inert

(eg nitrogen).

  In the first step of this process, the compound (B ') is contacted with a non-nucleophilic base, preferably in an inert organic solvent. This step is normally carried out at temperatures in the range of about 0.degree. C for about 0.5 to 3 hours using about 1 to 2, preferably 1 to 1.3 molar equivalents of non-nucleophilic base per mole of compound (B ') Suitable non-nucleophilic bases which can be used include for example, alkali metal hydrides such as sodium hydride, potassium hydride, etc .; alkali metal amides, for example lithium bis (trimethylsilyl) amide; sodium bis (trimethylsilyl) amide; potassium bis (trimethylsilyl) amide; lithium diethylamide; lithium diisopropylamide; the

  sodium dimethylamide, etc. Sodium hydride is generally preferred, since it has been very successful and is readily available commercially.

  Alkali metal amides, and naturally also alkali metal hydrides, are generally known compounds which can be prepared by

  known, or by obvious modifications of these methods.

  For example, the alkali metal amides can be prepared by the reaction of a secondary amine with a

alkali metal alkyl.

  Suitable inert organic solvents which can be used include, for example, tetrahydrofuran, dioxane, dimethoxyethane, diethyl ether, diisopropyl ether, and the like, and mixtures thereof. The second step can be carried out by contacting the compound (B ") with an alkyl base, preferably in an inert organic solvent. As indicated above, this process step is advantageously carried out in situ with the reaction product mixture of the first step Normally, the second step is conducted in temperature ranges of about -78 to 0 ° C for about 1 to 4 hours using about 1 to 2, preferably 1 to 3, molar equivalents of alkyl base per mole of compound (B ") Suitable alkyl bases which can be used include, for example, alkyl-alkali metals, Grignard alkyl reagents, etc. n-Butyllithium is advantageously used, since it gives good results and It is readily available commercially. Suitable solvents which can be used include those listed above with respect to the first step, etc. The third step can be carried out by contacting the compound (B '' ') with the appropriate R' '' halide bearing the desired R '' 'group, preferably in an inert organic solvent. The third step is also driving normally in situ with the product mix

  reactions of the second step.

  The third step of this process is normally conducted at temperatures in the range of about -30 to 30 ° C, preferably 22 to 25 ° C for about 1 to 18 hours, preferably 1 to 5 hours using about 1 to 10 moles, preferably 1 to 1.5 moles of R '' 'X' per mole of B '' Suitable inert organic solvents include those indicated above

  about the first step of this process, etc. The halides R '' 'X' are generally known compounds which can be prepared by known methods or by obvious modifications of these processes (for example by substitution of reactants and appropriate solvents).

  The starting materials of formula (Bg) can be prepared by the procedure diagrammatically shown below: ## STR2 ##

(B) (C ')

  wherein R 1 is a lower alkyl radical (preferably methyl) and R, Y and X are as defined above. This process can be carried out advantageously by contacting the compound (B) with the compound (C ') and a strong base under reactive conditions, preferably in

an inert organic solvent.

  Normally, this process is carried out using the same conditions as described above with respect to the preparation of compound (A), except that the reactant C 'is used in place of the reactant C The reactants of formula C 'are simple alkyl alkoxyacetates, for example methyl methoxyacetate. The preparation of

  these compounds are well known in the prior art.

  The compound of formula (I) in which one or both of R and R are substituted may be prepared by alkylating the amino group of the corresponding compounds of formula I according to the scheme:

X X

jo + R 212 '' -> 'f

H R 1

(I '')

  wherein R, R 1, X and Y are as defined above; R has the definition given for R, but is not

  not hydrogen, and R 2 Z 'is an alkylating agent having the appropriate R 2 group or R group if dialkylation is desired.

  This process can be carried out by contacting the compound (I ") with a suitable alkylating agent capable of

  to alkylate primary or secondary amino groups.

  For example, this operation can be carried out by bringing the compound (I ") into contact with the iodide or the bromide of R, preferably in an inert organic solvent and especially in the presence of a base serving as an acceptor. This process is carried out at temperatures in the range of about 0 to about C, preferably 20 to 45 C for about 1.0 to 72.0, preferably 2.0 to 18.0 hours. it is desired to perform a monoalkylation, then normally about 1.0 to 1.1 mole of R-halide reaction per mole of compound (I ") is used. If it is desired to alkylate the two amine hydrogen atoms, then then normally uses about 1.9 to 4.0 moles of R 2 halide per mole of compound (I ") o In case it is desired to prepare the compound in which R 2 is an alkoxyalkyl or alkylthioalkyl group it is recommended to use a large excess of R 2 'halide even when monoalkylation is desired; 3 to 6 moles of R 2 'Z "per mole of compound I" Alkylation can be continued in a second step, if necessary Similarly, a variation of R 1 and R 2 can be carried out by alkylating firstly, that one of the two amine hydrogen atoms, then alkylating the second amine hydrogen atom with a 2 'alkylating agent bearing a different R group. The compounds in which R and R form together with the amine nitrogen atoms a saturated heterocycle may be prepared using the appropriate alkylating agent of the formula Z "- (CH 2) 2 5 -Z" wherein Z "is C 1 or Br unsaturated heterocycle NRN can be prepared using the appropriate cis-alkenyl dihalide wherein one of the halogen atoms is on each terminal carbon atom of the alkenyl group. Suitable inert organic solvents which can be used include, for example, liquid halogenated alkanes, such as methane chloride hylene, carbon tetrachloride or dichloroethane; Tetrahydrofuran, etc., can also be used. Advantageous bases for use as acceptors include, for example, the bases described above with respect to the reaction of the compound (B) with

the compound (C).

  Compounds of formula (II ") in which R 1 is a lower alkyl radical (for example methyl) and R is hydrogen or a lower alkyl radical, are advantageously prepared using dialkyl sulfate as alkylating agent. this preparation by contacting the compound of formula I in which one or both R 1 and R 2 groups 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 strong base and normal phase transfer, this operation is conducted at temperatures in the range of about 0 to 100 C, preferably 20 to 45 C using about 1 0 to 4.0 moles of dialkyl sulphate per mole of compound I An excess of base is used, normally about 2.5 moles. This compound is also advantageously used in an inert organic solvent such as Examples are methylene chloride, carbon tetrachloride, dichloroethane, tetrahydrofuran and the like. Suitable strong bases which can be used include, for example, sodium hydroxide, potassium hydroxide, sodium ethoxide, sodium carbonate, potassium carbonate, etc. Suitable phase transfer agents are agents that transfer hydrophilic ions into a lipophilic organic medium and include, for example, benzyltriethylammonium chloride, tetra-n-butylammonium chloride, methyltrioctylammonium chloride, and the like. The compatible salts of formula (I) may be prepared by conventional methods, for example by treatment of the compound of formula (I) in which R 1 and / or R 2 represent hydrogen with a suitable strong base such as, for example , n-butyllithium, sodium hydride, potassium hydride, etc. carrying the desired cation, by conventional operations to form the corresponding cation salts R 1 and / or R 2 The enolates can be prepared by treatment R 1 and / or R 2 cationic salts with a base by conventional procedures Other variations relating to the cation of the salt can also be carried out by ion exchange with an ion exchange resin

presenting the desired cation.

  General Process Conditions In the processes described above, it is generally preferable to separate the respective products before proceeding to the next step in the reaction sequence, except in the cases described as in situ step or unless otherwise specified. can be isolated from their respective mixtures of reaction products by any suitable separation and purification process, for example by recrystallization and chromatography. Suitable separation and purification operations are illustrated, for example,

  in the examples given below.

  Generally, the above-described reactions are conducted as a liquid phase reaction and thus the presomation is generally not important except in

  the extent to which it affects the temperature (boiling point) when the reactions are conducted at reflux.

  Consequently, these reactions are generally conducted at pressures ranging from about 40 to 400 kPa and they are advantageously conducted at a pressure of the order

  atmospheric or ambient pressure.

  It should also be noted that when representative or preferred operating conditions (e.g. reaction temperatures, times, molar ratios of reactants, solvents, etc.) have been indicated, other operating conditions could also be The optimum reaction conditions (eg temperature, reaction time, molar ratios, solvents, etc.) may vary with the particular reactants or organic solvents used, but can be determined by

  classic methods of optimization.

  When mixtures of optical isomers are obtained, the respective optical isomers can be isolated by standard resolution procedures. Geometric isomers can be separated by conventional separation procedures which are based on differences.

  physical properties between geometric isomers.

  Definitions As used herein, the following terms have the following meanings unless otherwise stated: "Lower alkyl" refers to straight-chain and branched-chain alkyl groups having a total of 1 to 4 carbon atoms carbon and include primary, secondary and tertiary alkyl groups.

  Lower alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl.

  The term "alkylene" refers to straight chain and branched chain alkylene groups and includes, for example, CH 3 groups.

-CH 2; -CH 2 -CH 2; -CH 2 -CH 2-,

  etc. The term "lower alkenyl" refers to alkenyl groups having 2 to 6, preferably 2 to 4 carbon atoms and includes, for example, vinyl, 1-propenyl, 2-propenyl, 1-methylvinyl, 1-butenyl , 2-methylprop-1-enyl, etc. The expression "lower alkoxy" corresponds to

  in the group -OR 'in which R' is a lower alkyl radical.

  The term "lower alkylthio" refers to

  in the group -SR 'wherein R' is a lower alkyl radical.

  The term "lower alkoxyalkyl" refers to the group R'OR "wherein R 'and R" independently represent straight or chain alkyl groups.

  branched having 1 to 3 carbon atoms.

  The expression "(lower alkyl) -thioalkyl"

  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 a lower alkyl radical and R "is an alkylene radical having 1 to 4 carbon atoms, the chain of which may be Examples of alkoxycarbonylalkyl groups include -CH 2 C (O) OCH 3 groups; -CH (CH 3) C (O) OC 2 H 5, etc. The term "halo" refers to the fluoro, chloro, bromo and iodo radicals. The term "lower haloalkyl" refers to haloalkyl groups having 1 to 4 carbon atoms and 1 to 3 halo radicals independently selected from fluoro radicals, chloro, bromo and iodo The group

  Lower haloalkyl preferably has 1 or 2 carbon atoms.

  The term "lower halogenalkoxy" refers to

  "lower alkoxy" groups having 1 to 3 halo radicals independently selected from the group of fluoro, chloro, bromo and iodo radicals.

  The term "aryl" refers to aryl groups having 6 to 10 carbon atoms and includes, for example, phenyl, naphthyl, indenyl. The aryl group is normally a phenyl or naphthyl group, expected

  compounds having such groups are easier to obtain commercially than other aryl compounds.

  The term "substituted aryl" refers to aryl groups having 1 to 3 substituents independently selected from the group consisting of lower alkyl, lower alkoxy, halogenonitro or haloalkyl having 1 to 3 carbon atoms and 1 to 3 halogen atoms. Examples of substituted aryl groups include 2-fluorophenyl, 2-chlorophenyl, 2,6-dimethylphenyl, 4-fluorophenyl, 2-methylphenyl, 2-chloro, 3chloromethylphenyl, 2-nitro, 5-methylphenyl, 276-dichlorophenyl, 3-trifluoromethylphenyl , 2-methoxyphenyl, 2-bromonaphth-1-yl, 3-methoxyphenyl-1-yl, etc. The term "arylalkylene" refers to the group Ar R wherein Ar is an aryl group and R is an alkylene group having 1 to 3 carbon atoms and includes straight chain and branched chain alkylene groups such as methylene, ethyl, 1 methyl ethyl and propyl. The term "(substituted aryl) alkylene" or "ring-substituted arylalkylene" refers to the group of formula Ar'R, wherein Ar 'is an aryl radical

  substituted and R is an alkylene radical as defined with respect to the arylalkylene group.

  The term "saturated nitrogen heterocycle" as used herein in connection with R and R of formula I refers to groups of formula N

H 2 C / N CH 2

(CH 2) n

  wherein N is 1, 2 or 3.

  The term "unsaturated nitrogen heterocycle" as used herein in connection with R 1 and R 2 of formula I refers to groups of formulas:

N N N N

% I i I I t N i N N N and

U 9

  The term "compatible salts" refers to salts which do not significantly alter the herbicidal properties of the compound from which they are derived. Suitable salts include cationic salts such as, for example, cationic salts of lithium, sodium, potassium, metals. alkaline earth, ammonium, quaternary ammonium salts, & c. The term "laboratory temperature" or

  "room temperature" refers to a temperature of about 10 to 25 C.

  Usefulness The compounds of formula (I) are endowed with herbicidal activity both pre-emergence and post-emergence and

  have a particularly high pre-emergence herbicidal activity.

  In general, for post-emergence applications, the herbicidal compounds are applied directly to the

  foliage or other parts of plants For pre-emergence applications, the herbicidal compounds are applied to the present or future growth medium of the plant.

  The optimum amount of herbicidal compound or composition will vary with the particular plant species, and the degree of potential plant development, and the particular part of the plant that is affected, and the degree of contact. The optimal dosage may also vary. with the general layout or environment (eg protected areas such as greenhouses compared to exposed areas such as fields) as well as the type and degree of herbicidal effect desired. raised and post-emergence, the compounds of the invention are applied at levels of about 0.02

  at 60 kg / ha, preferably from about 0.02 to 10 kg / ha.

  Also, although the compounds can theoretically be applied in undiluted form, they are generally applied in actual practice in the form of a composition or formulation comprising an effective amount of one or more compounds and a acceptable carrier An acceptable or compatible carrier (acceptable carrier in agriculture) is a carrier which does not significantly alter the desired biological effect produced by the active compounds, except for the dilution of the compounds. Normally, the composition contains approximately 0.05 to 95% by weight of the compound of formula W or mixtures of such compounds Concentrates may also be prepared at high concentrations, intended to be diluted before application. The support may be a solid, liquid or aerosol support. The actual compositions may affect the form of granules, powders, dusts, solutions, emulsions, suspensions, aerosols, etc. Suitable solid carriers which may be used include, for example, natural clays (such as kaolin, attapulgite, montmorillonite, etc.), talcs, pyrophyllite, diatomaceous earth, fine particulate synthetic silica, Calcium aluminosilicate, tricalcium phosphate, etc. Organic materials such as, for example, nut shell flour, cotton seed husks, wheat flour, sawdust, Suitable liquid diluents which may be used include, for example, water, organic solvents (e.g. hydro carbides such as benzene and toluene, methylsulfoxide, kerosene, diesel, fuel oil, petroleum naphlita, etc.) Suitable aerosol carriers that can be used include conventional carriers such as halogenated alkanes, etc. The composition may also contain various promoters and surfactants which promote the rate of transport of the active compound into the plant tissue, for example, organic solvents, wetting agents and oils and, in the case of pre-emergence application, agents which reduce the leaching ability of the compound or

  which otherwise promote stability in the soil.

  The composition may also contain other adjuvants, stabilizers, conditioning agents, insecticides, fungicides and, where appropriate, other compounds

herbicides, compatible.

  At reduced doses, the compounds of the present invention also exert an influence on plant growth and can be used to modify the normal growth pattern of green plants. The compounds of formula (I) can be applied as plant growth substances in the pure form, but they are applied more pragmatically, as in the case of a herbicidal application, in combination with a carrier. same types of carriers as those mentioned above with respect to herbicidal compositions Depending on the desired application, the composition influencing plant growth may also contain, or be applied in combination with, other compatible ingredients such as desiccants, defoliants, surfactants, adjuvants, fungicides and insecticides Normally, the composition influencing the growth of plants contains in total about

  0.005 to 90% by weight of the compound (s) of formula (I) according to whether the composition is intended to be applied directly or firstly diluted.

  A further understanding of the invention is given by the following Preparation and Non-Limiting Examples. Unless otherwise specified, all temperatures and ranges of temperature are expressed in degrees Celsius and the term "room temperature" or "temperature of the laboratory "refers to a temperature of about 20-25 C The term

  "percent" or the sign "%" refers to the weight percent and the term "moles" refers to grams-molecules.

  The term "equivalent" refers to the amount of reagent, in moles, equal to the moles of the preceding or following reactant indicated in this example by a finite number of moles or a finite value by weight or by volume. The magnetic resonance spectra of protons (RMP or NMR), when mentioned, were determined at 60 M Hz, the signals are assigned as singlet (s), large singlet (ls), doublet (d), doubledoublet (dd), triplets (t), doubletriplets (dt), quadruplets (q) and multiplets (m); and cps means a number of cycles per second. Similarly, where necessary, examples are repeated to produce an additional amount of deparet material for subsequent examples.

EXAMPLES

Example 1

  (3-trifluoromethylphenyl) -benzylcarbonylacetonitrile In this example, 4.91 g of sodium ethyl was added to 110 ml of anhydrous ethanol at laboratory temperature and stirred until all the sodium was dissolved. A mixture containing 18.76 g of (3-trifluoromethylphenyl) acetonitrile and 21.73 g of ethyl phenylacetate was added dropwise and the resulting mixture was stirred at reflux for about 18 hours. The mixture was then poured into 300 ml. ml of water and extracted three times with ethyl ether. The pH of the extracted aqueous phase was adjusted to a value of about 1 with a 10% by weight aqueous solution of hydrochloric acid and the mixture was The organic phase was washed twice with saturated aqueous sodium bicarbonate solution, dried over magnesium sulphate and evaporated to dryness in vacuo to give the title compound.

  22.6 g of the title compound.

  Similarly, by adapting the procedure above to the use of phenylacetonitrile with a suitably substituted phenylacetonitrile and ethyl-substituted phenylacetate as starting materials, the following compounds can be prepared: 3-trifluoromethylphenyl) benzylcarbonyl-acetonitrile; (4-chloro-3-trifluoromethylphenyl) benzylcarbonylacetonitrile; (2-bromo-3-trifluoromethylphenyl) benzylcarbonylacetonitrile; (6-fluoro-3-trifluoromethylphenyl) benzylcarbonylacetonitrile; (4-methyl-3-trifluoromethylphenyl) benzylcarbonylacetonitrile; (5-methoxy-3-trifluoromethylphenyl) benzylcarbonylacetonitrile; (6-methyl-3-trifluoromethylphenyl) benzylcarbonylacetonitrile; (3,5-di-trifluoromethylphenyl) benzylcarbonylacetonitrile; (3-difluoromethoxyphenyl) benzylcarbonylacetonitrile; (3-trifluoromethoxyphenyl) benzylcarbonyl acetonitrile; (3-trifluoromethylphenyl) - (4-fluorobenzylcarbonyl) acetonitrile; (3-trifluoromethylphenyl) -1-naphthylmethyleneacetonitrile; (2-chloro-3-methylphenyl) -benzylcarbonylacetonitrile; (4-ethyl-3-methylphenyl) benzylcarbonylacetonitrile; (5-methoxy-3-chlorophenyl) benzylcarbonyl acetonitrile; (3-iodophenyl) benzylcarbonylacetonitrile; (3difluoromethylthiophenyl) benzylcarbonylacetonitrile; (3-trifluoromethylthiophenyl) benzylcarbonylacetonitrile; (3,5-diethoxyphenyl) benzylcarbonylacetonitrile; (3-bromophenyl) - (2-nitrobenzylcarbonyl) acetonitrile; (2-chloro-3-methylphenyl) benzylcarbonylacetonitrile; (3-bromo-2-ethylphenyl) -naphthylmethylenecarbonylacetonitrile; (2,3-dimethylphenyl) -beta-naphth-1-ylmethylcarbonylacetonitrile; (3-chlorophenyl) benzylcarbonylacetonitrile; (3-methylphenyl) benzylcarbonylacetonitrile; (3-tert-butoxyphenyl) -benzylcarbonyl-acetonitrile; (3-propylphenyl) benzylcarbonylacetonitrile; (3-bromophenyl) benzylcarbonylacetonitrile; (3-iodophenyl) - (3-nitrobenzylcarbonyl) acetonitrile; (3-trifluoromethylphenyl) - (2,3-dichlorobenzylcarbonyl) -acetonitrile; (3-methoxyphenyl) -1-naphthylmethylenecarbonylacetonitrile; (3-trifluoromethyl) - (3-chloro-8-fluoronaphth-1-ylmethylenecarbonyl) acetonitrile; (3-Trifluoromethyl) - [(2-trifluoromethyl-3-methyl-8-methoxy-naphth-1-yl) methylenecarbonyl] -acetonitrile (3-trifluoromethyl) - (inden-1-ylmethylenecarbonyl) -acetonitrile; and (3-trifluoromethyl) - (2-fluorinden-1-ylmethylenecarbonyl) -acetonitrile. Example 2 2-Phenyl-3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3-dihydrofuran In this example, a solution containing 21.8 g of (3-trifluoromethylphenyl) -benzylcarbonyl-acetonitrile dissolved in 60 ml of Acetic acid was treated by dropwise addition of 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 organic extracts were washed with saturated aqueous sodium bicarbonate solution, dried over magnesium sulphate and

  vacuum giving 8.4 g of a white solid which gave after drying 7.0 g of the title compound.

  Similarly, by adapting the above procedure to the compounds indicated in Example 1, the following compounds can be prepared: 2-phenyl-3-oxo-4- (5-chloro-3-trifluoromethylphenyl) -5-amino 2,3-dihydrofuran; 2-phenyl-3-oxo-4- (4-chloro-3-trifluoromethylphenyl) -5-amino-2,3dihydrofuran; 2-phenyl-3-oxo-4- (2-bromo-3-trifluoromethylphenyl) -5amino-2,3-dihydrofuran; 2-phenyl-3-oxo-4- (6-fluoro-3-trifluoromethylphenyl) -5-amino-2,3-dihydrofuran; 2-phenyl-3-oxo-4- (4-methyl-3-trifluoromethylphenyl) -5-amino-2,3-dihydrofuran; 2-phenyl-3-oxo-4- (5-methoxy-3-trifluoromethylphenyl) -5-amino-2,3-dihydrofuran; 2-phenyl-3-oxo-4- (6-methyl-3-trifluoromethylphenyl) -5-amino-2,3dihydrofuran; 2-phenyl-3-oxo-4- (3,5-di-trifluoromethylphenyl) -5-amino-2,3-dihydrofuran; 2-phenyl-3-oxo-4- (3-difluoromethoxyphenyl) -5amino-2,3dihydrofuran; 2-phenyl-3-oxo-4- (3-trifluoromethoxyphenyl) -530-amino-2,3-dihydrofuran; 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- (2chloro-3-methylphenyl) -5amino-2,3-dihydrofuran; 2-phenyl-3-oxo-4- (4-ethyl-3-methylphenyl) -5-amino-2,3-dihydrofuran; 2-phenyl-3-oxo-4- (5-methoxy-3-chlorophenyl) -5-amino-2,3-dihydrofuran; 2-phenyl-3-oxo-4- (3iodophenyl) -5-amino-2,3dihydrofuran; 2-phenyl-3-oxo-4- (3-fluifluoromethylthiophenyl) 5-amino-2,3-dihydrofuran; 2-phenyl-3-oxo-4- (3-trifluoromethylthiophenyl) -5-amino-2,3-dihydrofuran; 2-phenyl-3-oxo-4 (3,5-diethoxyphenyl) -5-amino-2,3-dihydrofuran; 2- (2-nitrophenyl) -3-oxo-4- (3-bromophenyl) -5-amino-2,3-dihydrofuran; 2-phenyl-3-oxo-4- (2chloro-3-methylphenyl) -5amino-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) -520-amino-2,3-dihydrofuran; 2-phenyl-3-oxo-4- (3-chlorophenyl) -5-amino-2,3dihydrofuran; 2-phenyl-3-oxo-4- (3-methylphenyl) -5-amino-2,3dihydrofuran; 2-phenyl-3-oxo-4- (3-butoxyphenyl) -5-amino-2,3dihydrofuran; 2-phenyl-3-oxo-4- (3-propylphenyl) -5-amino-2,3dihydrofuran; 2-phenyl-3-oxo-4- (3-bromophenyl) -5-amino-2,330 dihydrofuran; 2- (3-nitrophenyl) -3-oxo-4- (3-iodophenyl) 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-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-trifluoromethyl-1-yl) -5-methyl-2,3-dihydrofuran-2-indene-1-yl-3-oxo; (3-trifluoromethylphenyl) 5-amino-2,3-dihydrofuran and 2- (2-fluoren-1-yl) -3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3dihydrofuran Example 3 2-methyl-3-oxo-4- (3-trifluoromethylphenyl) 5-amino-2,3dihydrofuran 100 ml of ethanol was charged to a 500 ml three-necked round-bottomed dry flask equipped with a stirrer

  mechanical system, a dropping funnel and a reflux condenser.

  3.5 g of sodium was added to the solvent with stirring.

  After all of the metal had dissolved, a solution of 13.0 g of ethyl L - (+) - lactate and 18.5 g of m-trifluoromethylphenylacetonitrile in 30 ml of ethyl acetate was added dropwise to the reaction mixture. The mixture was red-intense in color and when the addition was complete, it was refluxed overnight (about 18 hours). The mixture was then cooled to room temperature and added to 300 ml. ml of water, and the resulting mixture was acidified (about 1 H) with 10% hydrochloric acid. The mixture was then extracted with ether (three times), and the organic extracts summer

  washed (twice) with saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate and concentrated in vacuo to give a thick oil.

  This oil was taken up in a mixture of ether and petroleum ether, and the desired compound crystallized in the form of a yellow powder. Two crops of crystals were collected.

  totaling 4.7 g of the title compound.

  Similarly, by adapting the above procedure to the use of correspondingly substituted starting materials, the following compounds can be prepared: 2-ethyl-3-oxo-4- (3-trifluoromethylphenyl) -5amino-2, 3-hydrofuranne; 2-ethyl-3-oxo-4- (5-chloro-3-trifluoromethylphenyl) -5-amino-2,3-dihydrofuran; 2-Cyclopentyl-3-oxo-4 (3-trifluoromethylphenyl) 5-amino-2,3-dihydrofuran; 2-vinyl-3-oxo-4- (3-trifluoromethylphenyl) -5amino-2,3-dihydrofuran-2-allyl-3-oxo-4 (3-trifluoromethylphenyl) -510-amino-2,3-dihydrofuran; 2-allyl-3-oxo-4- (2-methoxy-3-trifluoromethylphenyl) -5-amino-2,3-dihydrofuran; 2-trifluoromethyl-3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3dihydrofuran; 2-methyl-3-oxo-4- (3-difluoromethoxyphenyl) -5amino-2,3dihydrofuran; 2-methyl-3-oxo-4- (3-trifluoromethoxyphenyl) -5amino-2,3dihydrofuran; 2- (2-Chlorovinyl) -3-oxo-4- (3-trifluoromethyl) phenyl-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) -5amino-2,3-dihydrofuran 2-vinyl-3-oxo-4- (3-methyl-4-methoxyphenyl) -5-amino-2,3-dihydrofuran 2-allyl-3-oxo-4- (3,6-Dimethylphenyl) -5-amino-2,3-dihydrofuran-2-trifluoromethyl-3-oxo-4- (3-trifluoromethyl-4-bromophenyl) -5-amino-2,3-dihydrofuran 2- (2-chlorovinyl) -3- oxo-4- (3-nitro-4-methylphenyl) -5-amino-2,3-dihydrofuran, 2-methyl-3-oxo-4- (3-methoxyphenyl) -5-amino-2,3-dihydrofuran; methyl-3-oxo-4- (3-difluoromethylthiophenyl) -5amino-2,3-dihydrofuran, 2-methyl-3-oxo-4- (3-trifluoromethylthiophenyl) -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-dihydrofuran, 2-allyl-3-oxo- 3,5di (trifluoromethyl) phenyl-α-amino-2,3-dihydrofuran; 2-trifluoromethyl-3-oxo-4- (4-fluorophenyl) -510-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) -5amino-2,3-dihydrofuran; 2-vinyl-3-oxo-4- (3-chloro-4-methoxyphenyl) -5amino-2,3-dihydrofuran; 2-allyl-3-oxo-4- (3,5-dimethylphenyl) -5-amino-2,3-dihydro-furan; 2- (trifluoromethyl) -3-oxo-4- (3-trifluoromethyl-5-bromophenyl) -5-amino-2,3-dihydrofuran; 2- (2chlorovinyl) -3-oxo-4- (3-fluoro-4-methylphenyl) -3-oxo-5-amino-2,3dihydrofuran; 2-phenyl-3-oxo-4- (3-methoxyphenyl) -5-amino-2,3-dihydrofuran-2-methyl-3-oxo-4- (3,5-difluorophenyl) -5-amino-2,3-dihydrofuran; 2-vinyl-3-oxo-4- (3,5-diethylphenyl) -5-amino-2,3dihydrofuran; 2-allyl-3-oxo-4- (3-propoxyphenyl) -5-amino-2,3-dihydrofuran; 2-trifluoromethyl-3-oxo-4- (3-fluorophenyl) -5amino-2,3dihydrofuran; 2-propyl-3-oxo-4- (3-bromophenyl) -3-oxo-5-amino-2,3dihydrofuran; 2-phenyl-3-oxo-4- (2-iodo-3-fluorophenyl) -5-amino-2,3dihydrofuran; 2-benzyl-3-oxo-4- (2-isopropoxy-3-trifluoromethylphenyl) 5-amino-2,3-dihydrofuran; 2- (3-chlorophenyl) -3-oxo-4- (2,3-dimethylphenyl) -5-amino-2,3-dihydrofuran; 2-Naphth-1-yl-3-oxo-4- (3-trifluoromethyl-4-bromophenyl) -5-amino-2,3-dihydrofuran; 2- (3-methylphenyl) -3-oxo-4- (3-butyl-4-methylphenyl) -3-oxo-5-amino-2,3dihydrofuran; 2- (3-fluorophenyl) -3-oxo-4- (3-chlorophenyl) -510-amino-2,3-dihydrofuran; 2- (2,3,5-Trifluorophenyl-3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3-dihydrofuran, 2- (3-methylnaphth-1-yl) -3-oxo-4- ( 3-trifluoromethylphenyl) -5-amino-2,3-dihydrofuran, 2- (2-chlorovinyl) -3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3dihydrofuran, 2-fluoromethyl-3-oxo 4- (3-Trifluoromethylphenyl) -5-amino-2,3-dihydrofuran-2-methoxymethylene-3-oxo-4- (3-trifluoromethyl-phenyl) -5-amino-2,3-dihydrofuran 2-propoxymethylene-3-oxo-4- 4- (3-Trifluoromethylphenyl) -5-amino-2,3-dihydrofuran, 2-ethoxymethylene-3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3-dihydrofuran, 2- (2-methoxypropyl) -3-oxo 4- (3-trifluoromethylphenyl) -5-amino-2,3dihydrofuran, 2-methylthiomethylene-3-oxo-4- (3-trifluoromethylphenyl) 5-amino-2,3-dihydrofuran, and

  2- (1-propylthioethyl) -3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3dihydrofuran.

Example 4

  (3-trifluoromethylphenyl) methoxyacetyl-acetonitrile In this example, 5.6 g of sodium metal was added to 120 ml of anhydrous ethanol at laboratory temperature, under a nitrogen atmosphere, resulting in evolution of hydrogen When the release of hydrogen

  was terminated, a mixture containing 30 g of (3-trifluoromethylphenyl) acetonitrile and 18.5 g of methoxy-

  The mixture was then added to 300 ml of water and extracted three times with petroleum ether. acidified with 10% aqueous hydrochloric acid to a pH of about 1 and extracted three times with ethyl ether. The extraction phases with ethyl ether were combined, washed two times. The mixture was evaporated under high vacuum to give an oil which was triturated with ethyl ether. This mixture was then filtered. to remove the solids and the filtrate was

  evaporated in vacuo to give 36.9 g of the title compound as a brown solid.

  Also, 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 compound can be prepared.

indicated in the title.

Example 5

  (3-trifluoromethylphenyl) -2-methoxyisovaleryl-acetonitrile In this example, 10 g of (3-trifluoromethylphenyl) methoxyacetylacetonitrile were added dropwise to a suspension of 1.87 g of sodium hydride in 20 ml of tetrahydrofuran. at about 0.degree. C. under a nitrogen atmosphere, which resulted in the evolution of hydrogen. When hydrogen evolution was no longer observed, the mixture was cooled to about 78.degree. C. and the mixture was added dropwise at room temperature. The mixture was stirred for 1.5 hours at -78 ° C., then it was stirred at about 0 ° C. for 20 minutes. 3.9 ml (about 6.64 g) of 2-iodopropane were added dropwise and the mixture was stirred overnight (about 14-16 hours). The mixture was added to water, acidified with 10% aqueous hydrochloric acid and extracted three times with ethyl ether. The extracts were collected, dried over sodium hydroxide and dried. magnesium ulfate and concentrated in vacuo to give 11.4 g of the title compound in the form of

of an oil.

  Similarly, by adapting the same procedure, but using the appropriate iodide, bromide or alkyl, aryl or aryl chloride, in place of iodopropane, the following compounds can be prepared: (3-trifluoromethylphenyl) - (2-methoxy-3-phenylpropionyl) acetonitrile; (3-trifluoromethylphenyl) -2-methoxy-3- (2-fluorophenyl) propionyl] acetonitrile; (3-trifluoromethylphenyl) -2-methoxy-3- (3-methylphenyl) propionyl] acetonitrile (3-trifluoromethylphenyl) -2-methoxy-3- (215-ethoxyphenyl) propionyl] acetonitrile; (3-trifluoromethylphenyl) -2-methoxy-3- (3-nitrophenyl) propionyl] acetonitrile; (3-trifluoromethylphenyl) -2- [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] acetonitrile; (3-trifluoromethylphenyl) -2-methoxy-3- (2,2-fluoro-2 ', 2'-dichloroethylphenyl) propionyl] acetonitrile; (3-trifluoromethylphenyl) -2-methoxy-3- (2,3-dichloro-6-methylphenyl) propionyl] acetonitrile; (3-trifluoromethylphenyl) - (2-methoxy-4-phenylbutyryl) acetonitrile; (3-trifluoromethylphenyl) -2- (2-methoxy-5- (2-bromophenyl) valeryl] acetonitrile; (3-trifluoromethylphenyl) - (2-methoxy-3-methyl-4-phenylbutyryl) acetonitrile; (3-trifluoromethyl) - (2-methoxy-3-naphth-1-yl) propionyl) acetonitrile; (3-trifluoromethyl) - [2-methoxy-3- (2-fluoronaphth-1-yl) propionyl] acetonitrile; (3-trifluoromethyl) - [2-methoxy-3- (3-butylnaphth-1-yl) propionyl] acetonitrile; (3-Trifluoromethyl) -2-methoxy-3- (5-methoxynaphth-1-yl) propionyl] acetonitrile; (3-trifluoromethyl) -2- (3-methoxy-3- (6-nitronaphth-1-yl) propionyl] acetonitrile; (3-Trifluoromethyl) - 2 - methoxy-3- (7-trifluoromethyl-1-yl) propionyl] acetonitrile; (3-Trifluoromethyl) -2-methoxy-3- (2-chloro-810-methylnaphth-1-yl) propionyl] acetonitrile (3-trifluoromethyl) -2-methoxy-3- (3-methoxy-5-nitro-7-fluoromethylnaphthol) 1yl) propionyl_ / acetonitrile; (3-trifluoromethyl) - (2-methoxy-4-naphth-1-yl butyryl) acetonitrile; (3-trifluoromethyl) -? - 2-methoxy-5- (8-fluoronaphth-1-yl) valeryl / acetonitrile; (3-trifluoromethyl) -2-methoxy-3-methyl-3- (7-methoxynaphth-1-yl) propionyl] acetonitrile; (3-trifluoromethylphenyl) - (2-methoxy-3-indene-120-ylpropionyl) acetonitrile; and

  (3-Trifluoromethylphenyl) - [2-methoxy-3- (2-fluorin-1-yl) propionyl] acetonitrile.

By similarly adapting the above procedure to the use of other (monosubstituted or disubstituted phenyl) - (methoxyacetyl) acetonitriles in place of (3-trifluoromethylphenyl) - (2-methoxyacetyl) acetonitrile, the derivatives can be prepared. monosubstituted phenyls

  or corresponding disubstituted compounds of the above compounds.

Example 6

  2-Isopropyl-3-oxo-4- (3-trifluoromethylphenyl) -5-amino 2,3-dihydrofuran In this example, a mixture containing 11.4 g of (3-trifluoromethylphenyl) - (2-methoxyisovaleryl) acetonitrile and 7.8 Concentrated sulfuric acid in 50 ml of acetic acid was heated at reflux for 30 minutes and then concentrated by evaporation in vacuo. The concentrate was mixed with diethyl ether, washed three times with an aqueous solution of sodium hydroxide. 1 N sodium, dried over magnesium sulfate and concentrated by evaporation to give an oil. The oil was triturated in a mixture of 20% (by volume) ethyl acetate and 80% petroleum ether and was allowed to stand overnight (145 hours) The solids were collected by filtration and washed three times with a mixture of 20% (by volume) ethyl acetate and 80% petroleum ether.

  giving 2.9 g of the title compound.

  Similarly, by adapting the above procedure to the use of trifluoromethylphenyldimethoxyacetylacetonitrile, which can be prepared by the procedure of Example 1, and the other products indicated in Example 5, the following compounds can be prepared: 2-methoxy-3-oxo-4- (3-trifluoromethylphenyl) -515-amino-2,3-dihydrofuran; 2-benzyl-3-oxo-4- (3-trifluoromethylphenyl) -5amino-2,3-dihydrofuran; 2- (2-Fluorobenzyl) -3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3dihydrofuran; 2- (3-methylbenzyl) -3-oxo-4- (3-trifluoromethylphenyl) -5amino-2,3-dihydrofuran; 2- (2-ethoxybenzyl) -3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3-dihydrofuran; 2- (3-Nitrobenzyl) -3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3-dihydrofuran; 2- (4-Fluorobenzyl) -3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3dihydrofuran; 2- (2-trifluoromethylbenzyl) -3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3-dihydrofuran; 2- (2-Chloro-3-propylphenyl) -3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3dihydrofuran 2- (2-nitro-3-methoxyphenyl) -3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3-dihydrofuran; 2- (2-fluoro-3-2 ', 2'-dichloroethylbenzyl) -3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3dihydrofuran; 2- (2,3-dichloro-6-methylbenzyl) -3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3-dihydrofuran; 2- (Beta-phenethyl) -3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3-dihydrofuran; 2 - [3- (2-bromophenyl) propyl] -3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3dihydrofuran; 2 - [1-methyl-2- (phenyl) ethyl] -3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3-dihydrofuran; 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-ylmethylene) -3-oxo-4- (3-trifluoromethylphenyl) -5amino-2,3-dihydrofuran; 2- (7-trifluoromethylnaphth-1-ylmethylene) -3-oxo4- (3-trifluoromethylphenyl) -5-amino-2,3-dihydrofuran; 2- (2-chloro-8-methylnaphth-1-ylmethylene) -3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3-dihydrofuran; 2- (3-methoxy-5-nitro-7-fluoromethylnaphth-1-yl) -3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3-dihydrofuran; 2- (beta-naphth-1-ylethyl) -3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3-dihydrofuran; 2β- (8-fluoronaphth-1-yl) ethyl-7-3-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-indene-1-ylmethylene-3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3-dihydrofuran; and

  2- (2-Fluorinden-1-ylmethylene) -3-oxo-4- (3-trifluoromethylphenyl) -5amino-2,3-dihydrofuran.

  Similarly, by adapting the procedure above to the use of the corresponding mono and disubstituted analogues of the starting material for the compounds

  above, the 4- (3-methylphenyl) analogs can be prepared; 4- (3-beta-fluorethoxyphenyl); 4- (3-

  difluorométhylènethiophénylique); 4- (3-chlorophenyl);

  4- (2-bromo-3-trifluoromethylphenyl) and corresponding 4- (2-methyl) difluoromethylethiophenyl of the above compounds.

Example 7

  2-phenyl-3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino2,3dihydrofuran In this example, about 1 g of solid sodium hydroxide in 4.0 ml of water was added to a mixture of 10 ml. 3 g of 2-phenyl-3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3-dihydrofuran in 50 ml of methylene chloride at room temperature, then 1.19 g of dimethyl sulfate and 0.21 g of benzyltriethylammonium chloride The resulting two-phase mixture was stirred at laboratory temperature for about 2 hours, then washed three times with water, dried over magnesium sulfate, and then concentrated by evaporation under vacuum. The residue was then purified by chromatography on silica gel, the elution being carried out with mixtures of tetrahydrofuran and chloroform to give

the compound indicated in the title.

  Also, by adapting the above procedure to the use of the products indicated in Examples 2, 3 and 6 as starting materials, their corresponding 5-methylamino homologues 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-3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran; 2-phenyl-3-oxo-4 (2-bromo-3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran; 2-phenyl-3-oxo-4- (6-fluoro-3-trifluoromethylphenyl) -5-methylamino-2,3dihydrofuran; 2-phenyl-3-oxo-4- (4-methyl-3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran; 2-phenyl-3-oxo-4- (5-methoxy-3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran; 2-phenyl-3-oxo-4- (6-methyl-3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran; 2-phenyl-3-oxo-4- (3,5-di-trifluoromethylphenyl) -5-methylamino-2,3dihydrofuran; 2-phenyl-3-oxo-4- (3-difluoromethoxyphenyl) -5-methylamino-2,3-dihydrofuran; 2-phenyl-3-oxo-4- (3-trifluoromethoxyphenyl) methylamino-2,3-dihydrofuran; 2-phenyl-3-oxo-4- (3-trifluoromethylthiophenyl) -5-methylamino-2,3-dihydrofuran; 2- (4-fluorophenyl) -3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3dihydrofuran; 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-methylphenyl) -5-methylamino-2,3-dihydrofuran ; 2-phenyl-3-oxo-4- (5-methoxy-3-chlorophenyl) -5,20-methylamino-2,3-dihydrofuran; 2-phenyl-3-oxo-4- (3-iodophenyl) -5-methylamino-2,3-dihydrofuran; 2-phenyl-3-oxo-4- (3-difluoromethylthiophenyl) -5-methylamino-2,3-dihydrofuran; 2-phenyl-3-oxo-4- (3-trifluoromethylthiophenyl) -5-methylamino-2,3-dihydrofuran; 2-phenyl-3-oxo-4- (3,5-diethoxyphenyl) -5-methylamino-2,3-dihydrofuran; 2 (2-nitrophenyl) -3-oxo-4- (3-bromophenyl) -530 methylamino-2,3dihydrofuran; 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;

254758 '1

  2-phenyl-3-oxo-4- (3-methylphenyl) -5-methylamino-2,3-dihydrofuran; 2-phenyl-3-oxo-4- (3-butoxyphenyl) -5-methylamino-2,3-dihydrofuran; 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) -510-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 (2trifluoromethyl-3-methyl-8-methoxynaphth-1-yl) -3-oxo-4 (3-trifluoromethylphenyl) -5-methylamino-2,3dihydrofuran; 2-indene-1-yl-3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran; 2- (2-Fluorinden-1-yl) -3-oxo-4 (3-trifluoromethylphenyl) -5-methylamino-2,3dihydrofuran; 2-methyl-3-oxo-4- (3-trifluoromethylphenyl) -525 methylamino-2,3-dihydrofuran; 2-ethyl-3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran; 2-ethyl-3-oxo-4- (5-chloro-3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran; 2-cyclopentyl-3-oxo-4- (3-trifluoromethylphenyl) methylamino-2,3-dihydrofuran; 2-vinyl-3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran; 2allyl-3-oxo-4- (3-trifluoromethylphenyl) -535 methylamino-2,3dihydrofuran; 2-allyl-3-oxo-4- (2-methoxy-3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran; 2-trifluoromethyl-3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran; 2-methyl-3-oxo-4- (3-difluoromethoxyphenyl) -5-methylamino-2,3-dihydrofuran; 2-methyl-3-oxo-4- (3-trifluoromethoxyphenyl) -5-methylamino-2,3-dihydrofuran; 2- (2chlorovinyl) -3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3dihydrofuran; 2- (2-chlorovinyl) -3-oxo-4- (5-nitro-3-trifluoromethylphenyl) -5-methylamino-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-allyl-3oxo-4- (3,6-dimethylphenyl) -5-methylamino-2,3-dihydrofuran; 2-trifluoromethyl-3-oxo-4- (3-trifluoromethyl-420 bromophenyl) -5-methylamino-2,3-dihydrofuran; 2- (2-chlorovinyl) -3-oxo-4- (3-nitro-4-methylphenyl) -3-oxo-5-methylamino-2,3-dihydrofuran; 2-methyl-3-oxo-4- (3-methoxyphenyl) -5-methylamino-2,3-dihydrofuran; 2-methyl-3-oxo-4- (3-fluifluoromethylthiophenyl) -5-methylamino-2,3-dihydrofuran; 2-methyl-3-oxo (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-dihydrofuran; 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-2,3dihydrofuran; 2-propyl-3-oxo-4- (2-methoxy-3-chlorophenyl) 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) -510-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-methylamino2,3dihydrofuran; 2-methyl-3-oxo-4- (3,5-difluorophenyl) -5-methylamino-2,3dihydrofuran; 2-vinyl-3-oxo-4- (3,5-diethylphenyl) -5-methyl-amino-2,3-dihydrofuran-2-allyl-3-oxo-4- (3-propoxyphenyl) -5-methylamino-2,3dihydrofuran; 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) methylamino-2,3-dihydrofuran; 2-Benzyl-3-oxo-4- (2-isopropoxy-3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran; 2- (3chlorophenyl) -3-oxo-4- (2,3-dimethylphenyl) -5-methylamino-2,3dihydrofuran; 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-chlorophenyl) -5-methylamino-2,3-dihydrofuran; 2- (2,3,5-Trifluorophenyl) -3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3dihydrofuran; 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-2,3dihydrofuran; 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-C3-trifluoromethylphenyl) -5-methylamino-2,3dihydrofuran; 2-ethoxymethylen-3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran; 2- (2-methoxypropyl) -3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran; 2-methylthiomethylene-3-oxo-4- (3-trifluoromethylphenyl) -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-2,3dihydrofuran; 2- (3-methylbenzyl) -3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran; 2- (2-ethoxybenzyl) -3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran; 2- (3-nitrobenzyl) -3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3dihydrofuran; 2- (4-fluorobenzyl) -3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran; 2- (2-trifluoromethylbenzyl) -3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran; 2- (3-chloro-propylphenyl) -3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3dihydrofuran; 2- (2-nitro-3-methoxyphenyl) -3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran; 2- (2-fluoro-3-2 ', 2'-dichloroethylbenzyl) -3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran; 2- (2,3-dichloro-6-methylbenzyl) -3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran; 2- (Betaaphenethyl) -3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3dihydrofuran, 2- [3- (2-bromophenyl) propyl] -3-oxo-4- (3-trifluoromethylphenyl) -5 -methyl-2,3-dihydrofuran; 2- [1-methyl-2 (phenyl) ethyl] -3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3dihydrofuran; 2-Naphthyl-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-butylnaphth-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-tri) -2- fluoromethylphenyl) -5-methylamino-2,3-dihydrofuran, 2- (7-trifluoromethylnaphth-1-ylmethylene) -3-oxo4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran, 2- (2-chloro-8-methylnaphtha) 1-ylmethylene) -3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran; 2- (3-methoxy-5-nitro-7-fluoromethylnaphth-1-yl) -3-oxo-4- ( 3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran, 2-methoxy-3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran, 2- (beta-naphth-1-ylethyl) - 3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran; 2- (beta-fluoronaphth-1-yl) ethyl-3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino2,3 dihydrofuran, 2- [1- (7-methoxynaphth-1-yl) ethyl] -3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran, 2-indene-1-ylmethylene-3-oxo-2-ene 4- (3 trifluoromethylphenyl) -5-methylamino-2,3dihydrofuranne; and

  2- (2-Fluorinden-1-ylmethylene) -3-oxo-4- (trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran.

  Similarly, by approximately doubling the amount of dimethyl sulfate and extending the reaction time, the corresponding 5-dimethylamino homologues of the above compounds can be prepared using the same diethyl sulfate instead of dimethyl sulfate. ,

  the corresponding 5-ethylamino and 5-diethylamino homologs of the above compounds can be prepared.

Example 8

  2- (2-fluorophenyl) -3-oxo-4- (3-trifluoromethylphenyl) -520 allylamino-2,3dihydrofuran 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) -5-amino-2,3-dihydrofuran in 80 ml of methylene chloride at room temperature.

  laboratory, 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 laboratory temperature for about 18 hours, after which it was washed three times with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by chromatography. on silica gel eluting with chloroform to give 2.5 g of the title compound

the title.

  Also, by applying this procedure to the products listed in Examples 2, 3 and 6, their corresponding 5-allylamino analogues can be prepared. Similarly, by approximately doubling the amount of allyl bromide and sodium hydroxide, can prepare their

  corresponding 5-diallylamino analogues.

  In a similar way, using ethyl bromide instead of allyl bromide, it is possible to prepare

  the corresponding 5-ethylamino and 5-diethylamino analogs.

  By following the same procedure and using, respectively, methoxymethyl bromide, ethylthiomethyl bromide, methyl bromoacetate, methyl 2-bromobutyrate, 1,5-dibromopentane and cis-1,4-dibroimodbut -1, 3-diene instead of alkyl bromide, the corresponding 5-methoxymethylamino, ethylthiomethylamino, 5-methoxycarbonylmethylamino, 5- (1-methoxycarbonylpropylamino), 5-piperidin-1-yl and 5-pyrrole-1-yl analogous analogous analogs are obtained in the same way products listed in Examples 2, 3 and 6, for example 2-phenyl-3-oxo-4- (3-trifluoromethylphenyl) -5-methoxymethylamino-2,3-dihydrofuran; 2-methyl-3-oxo-4- (3-trifluoromethylphenyl) -methoxymethylamino-2,3-dihydrofuran; 2-ethyl-3-oxo-4- (3-trifluoromethylphenyl) -520-methoxymethylamino-2,3-dihydrofuran; 2-phenyl-3-oxo-4- (3-trifluoromethylphenyl) -5-ethylthiomethylamino-2,3dihydrofuran; 2-methoxy-3-oxo-4- (3-trifluoromethylphenyl) ethylthiomethylamino-2,3-dihydrofuran; 2-methyl-3-oxo-4- (3-trifluoromethylphenyl) -5-ethylthiomethylamino-2,3-dihydrofuran; 2-ethoxymethylene-3-oxo-4- (3-trifluoromethylphenyl) -5-ethylthiomethylamino2,3-dihydrofuran; 2-ethyl-3-oxo-4- (3-trifluoromethylphenyl) -530 ethylthiomethylamino-2,3-dihydrofuran; 2-phenyl-3-oxo-4- (3-trifluoromethylphenyl) -5-methoxycarbonylmethylamino-2,3-dihydrofuran; 2-methyl-3-oxo-4- (3-trifluoromethylphenyl) -5-methoxycarbonylmethylamino-2,3-dihydrofuran; 2-methylthiomethylene-3-oxo-4- (3-trifluoromethylphenyl) -5-methoxycarbonylmethylamino-2,3-dihydrofuran; 2-ethyl-3-oxo-4- (3-trifluoromethylphenyl) -5-methoxycarbonylmethylamino-2,3-dihydrofuran; 2-phenyl-3-oxo-4- (3-trifluoromethylphenyl) -5 (1-methoxycarbonylprop-1-yl) amino-2,3-dihydrofuran; 2-methyl-3-oxo-4- (3-trifluoromethylphenyl) -5 (1-methoxycarbonylprop-1-yl) amino-2,3-dihydrofuran; 2-fluoro-3-oxo-4- (3-trifluoromethylphenyl) -5 (1-methoxycarbonylprop-1-yl) amino-2,3dihydrofuran; 2-ethyl-3-oxo-4- (3-trifluoromethylphenyl) -510 (1-methoxycarbonylprop-1-yl) amino-2,3-dihydrofuran; 2-Naphth-1-yl-3-oxo-4- (3-trifluoromethylphenyl) -5- (1-methoxycarbonylprop-1-yl) amino-2,3dihydrofuran; 2-indene-1-yl-3-oxo-4- (3-trifluoromethylphenyl) -5- (1-methoxycarbonylprop-1-yl) amino-2,3-dihydrofuran; 2-phenyl-3-oxo-4- (3-trifluoromethylphenyl) -5-piperidin-1-yl-2,3-dihydrofuran; and 2-phenyl-3-oxo-4- (3-trifluoromethylphenyl) -5-pyrrole-1-yl-2,3-dihydrofuran, etc. Also, by applying the above procedures to the use of the 5-methylamino products of Example 7 as starting materials, 5- (N-methyl-N-allylamino), 5- (N-methyl) analogues can be prepared. methyl-N-ethylamino), - (N-methyl-N-methoxymethylamino), 5- (N-methyl-N-ethylthiomethylamino), 5- (N-methyl-N-methoxycarbonylmethylamino) and 5 (N-methyl-N- methoxycarbonylpropylamino).

Example 9

  2-phenyl-3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran lithium salt

J 2

  (R = -CH 3, R = Li) In this example, 5.4 ml of 1.6 M 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, then concentrated in vacuo to give 2.8 g of the title compound, under the

  form of a light brown solid substance.

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

Example 10

  The compounds listed in Table A below were prepared using the appropriate starting materials and the appropriate procedures described in the following procedures.

examples above.

T A B L E A U A

o F 3 C

R O R Z 2, -N O R

  Elemental Analysis Carbon Hydrogen Nitrogen Calculated Found Calculated Found Found Found Melting Point, C No R 1 R 2 R

9 10 11 12

  It CII 3 Cfil 2 ci 13 Ci 13 Ctl 2 ll Ci 3 CH 2 CHI 3 H

CII 3 CI CJI 2 H 3 (C 132) 2 CI 3

C Hl He

H CH 3

H CH 2 C Hi 3 H

H CH 3

H il He CH 2 CH 3 2 i 0 ** 0 l

2 -F 0

  4-F O 2 -F O 2 -F $ 2-F O 2-FO 2-C 10 F 2 -cl O

63.95 64.86

, 71 65.71 67.20 60 Y 53 61.54

62.47 62.47 63.32

64.12 58.78

  64 y 66 64.22 65.63 66> 55 67.76 59.66 61 122 62.95 60> 36 63.6 63.41 58 52 3.76 4.20 4.61 4.61 5 e 33 3 , 26 3.70 4.14 4.11 4 49 4.83 3.54

4> 19 4.65 4.83

12

  % 63 3.47 3.62 4 38 4.11 4.7 4.93 3.63

4.39 4.20 4.03 4.03 3.73

4> 15 3 99 3.84

3.84 3.69 3; 56 3> 81

4.78

3, 7/9 4.12

  3.98 3, 9 d 3.77 4; 12 4.45 4.08 4 f 02

3> 71 3, 85 4.05

  182-184 * 154-155 102 106 143-1 45 115-120 136-138 151-156 91-93 136-1383 53-6 () oil 201-2 (04 * * Decomposition 0 ** = Phenyl, for example , 2C 1 L = 2-chlorophenyl ul

4- 'U 14

  This Elemental Analysis No. R 1 R Carbon Calculated Found Calculated Hydrogen Found Nitrogen Calculated Found

  14 1 5 16 17 18 19 20 21 22 23 24 25

26 27 28 29 30

  31 32 C 2113 Cli 2 C 1 H 3 Il Il Il C 113 C Ht 2 CH 13 -C It 2 CII = CH 2 It -Cti 2 C (CI) = C 1 i 2 -CI 12 Cti = C (Cl) ) CH 3 -CI (Ci 13) COOC 2 15 Li Il el '3 C 113 CII 3 Cti 3 il C 112 C {13 Il Il Il HHHH il H Il Il -CI 13 Il C Hi 3 2-C 10 * 2 ## STR1 ## FO CH 3

0 0 0 0

i 1-

  59.77 59.77 61.55 64.86 64.86 64; 86 55,481 55.81 57.46 58.54 59.53 63.66

  56 03 61.0 61.8 63 d O 63.74 68.3 68.9 6955

  59.67 60.5 61.72 65.02 62 54 65.86 55958 55.37 57245 59.3 60, 11 62; 4

56.54 57.9 61.3 61.5 61.82

, 8 65.7 69, 2

  3.93 3.93 4.64 4.20 4.20 4.20 2.84 2.84 2.82 3.25 3.66 3.98 3.89

3> 8 4.2 478

3> 84 3.8 4.18

4 D 5

  4.05 4.05 4.79 4.43 4.27 4.25 3.05 3.09 3.14 3; 45 4.00 4.31 4.22 3.9 4.7 5.0 4.9 4; 1

  4.7 3.67 3, 67 3.42 4.2 () 4.2 () 4.2 y) 3.62 3 62 3.62 3.94 3.79

3266 3.71 5.45 3.55 3.4 3.3

4.13

3; 3.7 3.7; 5

3.72

3.89 3.77

  4.28 3.82 4.34 3.69 3.40 4.16 3. 84 3.71 4) 27 5.52

3 J 2 3.1 3.2

3.48 3.8 3.55

3; 6 Melting point,

  116-119 131-137 I 113-114 179-181 * 148-151 208-211 * 68-75 60-63 225-227 *

  191-193 * 63-65 oil 129-1 (30 oil 134-138 oil

* 123 12 174-179 139 14 3

  Ln O 0 * = Phenyl, for example, 2,6-di Fo = 2,6-difluorophenyl * = Decomposition y '. V CD 'T A B L A A U A (Continued) Elemental Analysis Melting Point, C No. R 1

R 2 R

  Calculated Carbon Found 33 (C 13 C 13 C 13 H 38 C 13 H 13 C 39 C 39 HI 4 (O CH 3 41 Ci 13 42 1 1 43 C 13 44 Hi 4 '13 (1 I 3 46 CII 3 C 11 C 11 C 11 H 11 C 11 H 11 H 11 C H 3 C 113 (C H C C 12 CH 3 (1 C 2 CH 3 (cii 2 ) 2 CH 3 CH (CH 3) 2 (C 13) (el (2) 3 Cfi 3 (cii 2) 3 C 113 cyclohexyl cyclohexyl 54,32

  56; 03 57.56 58.95 57.56 58, 95 58.95 60, 20 61.34 58.95 60.20 60; 20 61, 34 63.72 64> 59

54.91

75 58.87

59.35 60.08 59.59

  , 26 61.2 61.82 58 p 79 60.80 61.42 62.84

64.41 64.94

Calculated Hydrogen Found

3.29 3.54

  3.89 4.04 4.43 4.66 4.91 5.04 4.43 4.91

  4.91 5.12 4.91 5.19 5.35 5.84 5> 75 6211 4.91 5.23 5 35 5.36 5> 35 5.68 5.75 6.17 5.90 6 , 18 6.23 6 d 87

, 76 5.45 5.17

4.91 5.17 4.91 4.91 4.68 4.47 4.47 4.91

4 9 61 4.68 4.68 4.47 4.13 3.97

Calculated Nitrogen Found

, 42 5 39

, 32 5 34 5.47 5.17

, 08 4.56 4.46 5.0 4.85 4.9

, 03 3.6

4 1 I

-146 * 158-159 11 6 118 141-142

173-174 138-139

  -168 oil oil 155-156 121 -122 137-138 * 9 o

143-145 142-143

Ln o 4 _n oe

TABLE B

  R 21 R 2 No R 1 R 2 R Y Elemental Analysis Carbon Hydrogen Nitrogen Calculated Found Calculated Found Calculated Found

48 49 5 () 51 52

53 5

56 57 58 59 60

He he He

(11 3

  he (lt 3 Il Il ('13 CII "2 Cl I 2 11 l 3.i 3 lt He Il ll he he He He 3 He H he

2-CH 30 2-F O 2-C 10

  H It Cli 3 CH 3 CH 2 C Hi 3 C Hi 2 CH 3 (Ci 12) 2 CH 3 (Cli 2) 2 Clt 3

C 1 C 1 C 1

Cl Ci C 1 C 1 Ci C 1 Ci C 1 C 1 Ci

  68.11 63526 61.08 59.07 60.64 59> 07 66> 64 60.64 62.03 63.28 63> 28 62.03 63.28

  68.64 62> 3 62.21 59.1 61.11 57.16 62> 11 58 j 69 63.34 62.48 63.82 62, 13 63.58

4.67 3.62 3> 87 4.48

05 4; 48

, 05 5109 5.61 6.07

6> 7

> 61 6.07

4> 97

3 78

4> 06 4; 95 5> 52

> 46 5.83 6.86 6,52 5> 76 6; 49

  4.67 4.61 4> 19 6.27 5.90 6727 5; 5189 5.56 5; 27 5 27 5 56 5/27

  4> 96 4,17 4,33 6,24 6> 03 5173 6,05 5 67 5,96 5,93 5,89 5 63 5, 86

  Melting point, C -177 178-180) 185-193 * 117-12 {) * 177-178 1583-159 119-122 152-155 95-97 oil l 20-123 152-154 oil Ln m * = coposition * = Decomposit ion% ui -4 tn COD TABLEB (Continued) Elemental Analysis No R 1 R 2 RY Carbon Calculated Found Hydrogen Nitrogen Calculated Found Found 62 63

64 65 66 67

68 69 70 71

72 73 74

76

77 78 79 80

  ## STR2 ## ## STR2 ## ## STR2 ## 3 Ci 12 CIH 3 Il Il Ci 13 11 Il Il il 11 Il Il Il Il Il Il I Il il il il Il Il (CH 2) 2 Cil (ci 12) 2 ci 3 ci 12 3 CI 3) 2 CH 2 (CE 3) 2 C 12 (CH) 32 0 0 2-Cl O 2-C 10 2-C 10 2-FO 2-FO 2-FO 2-CH 2 2-CHI 30 2-C 1130 He II

C 1 C 1 C 1

  C 1 C 1 Br Br Br Br Br Br Br Br Br Br Br Br Btr Br I 3 C Ii 3

  64.40 64.40 62.04 63.29 64.41 58.20 59.32 60.35 52? 69 53991 55.05 55.19 56.37 57.46 59932 60 Y 35 61.31 49> 21 51.08 77 J O

  34 64.14 63.69 63.03 65; 66 54.8 60.79 61.01 54.59 53.77 55.3 55.14 58.0 57.59 58.48 60.36 62.98 48.01 50.35 76.3

  6.49 6.49 5.57 6.03 6.44 3.64 4.07 4.47 3.02 3.44 3.82 3.16 3.59 3.99 4507 4.47 4.84 3 , 73 4.26 5.7

  7> 11 6.65 6.05 6 72 6 J 83 3.79 4.36 4.74 3.26 3.47 3.97 3.57 3.41 4.31 4.22 4.68 5.16 4.41 4.28

9

, 01 5.01 5.57

, 27 5.01 4.24

  4,07 3.91 3.84 3 703> 57 4> 02 3.87 3.72 4.07 3.91 3.76 5> 23 4.97 5, 3

  , 33 4.67 6537 5.62 5 Y 47 3, 9 '7 3.93 37; 93 3.53 4.14 3.69 3.51

  3.94 4751 3.57 4.03 3.96 4> 24 5> 06 4} 86 5.1

  Melting point C 104-106 oil 156-157 85-91 130-131 177-178 * 181-185 161-163 202-204 205-207 144-147 190-191.5 172-173 157-159 167 208-21 (O 140-142

109-1 13 172-175 *

137-1141

  Ul Li * = Decomposition - ## EQU1 ## Calculated Carbon Found Found Hydrogen Found at Zote Calculated Trot 81 Ci H 3 It OC 3 77 4 77) 1 6,1 6> 4 5,0 (82 11 O O CH 3 72,6 73> 7 5,4 6) 6 50

  13 C 113 I 1 O OCH 3 73.2 72; 5 5> 8 5.9 4> 7

  84 C Hi 3 O OCHI (CH 3) 2 74.30 70.02 6 5 6.47 4333

  CHI 2 CH 3 II O UCH (CH 3) 2 74; 25 75,88 6:87 7:23 4; 15

  86 II il 2-C 11 OCH (CH 3) 2 74.28 73.58 6.55 6 85 4> 33 87 CI 13 il 2CI 130 OC Hi (C 113) 2 74.75 74> 35 6.82 6.95 4> 15 88 CII 2 CI 13 II 2-C 1130 O Ci (CH 3) 2 7 '519 73.63 7.17 17> 27 3.99 89 Il II 2-FO OCH (CH 3) 2 69.71 70: 7 5.54 5 y 74 4.28

  C 113 H 2 -F O OCH (Cl Cl 13) 2 70.37 69 66 5591 6.1 4.10

  91 H 2 C 10 OCH (CH 13) 2 66 38 68.29 4.07 4 P 36 5528 92 CH 357 CH 2 CH 3 CH 3 OCH (CH 3)> 2680 65975 6: 9 6; 6 5> 7 93 C 113 Hi CH 3 OCH (C'13) 2 68.97 68> 69 7.28 8.01 5 36 94 1 O -00 76.995 76> 3 5) 0 610 4.1

  C 1 H 3 H -00 77, 739 5: 3 5,6 3: 9

  961 C H 13 CH 3 O Y = C 1, X = C 1 62.1 62.9 4.3 4.7 4> O

  97 -CIH 2 (C "2 CH 2 O -CF 3 67> 55 72> 4 4, 85 5 JI 3.75

  961 is 2-phenyl-3-oxo-4- (3,4-dichlorophenyl) -5-dimethylamino-2,3dihydrofuran * = D 6 composition

  , 1 5.1 3 6 4.2 4 2 4.1 3: 8 4.1 4.2 4 2 L 5 42 5 6 6> 1 3.0 4.1

4/17 1

4> O 3> 8

Melting point, C ivé oc

  -152 141-1 44 128-133 1 185-188 * 3 111-113 7 149-151 3 134-135 9 134-136 5 150-151 5 191-193 8 171-173

151-155 5 114-115

73-78

163-167 133-137

1105-111

u 1 ru Ln 4 Coo -4

TABLE C

Cables of comparison X

Y O O +

  R R (unless otherwise specified, X = H and R = H) Elemental analysis Fusing point, Carbon Hydrogen Nitrogen o, No 1 1 {2 R Y Calculated Found Calculated Found Found Found ul

C-I C-2 C-3 C-4 C-5 C-6 C-7 C-8

  C-9 Ci 13 H He Il CII 3 C Hi 3 C It 3 113 Il 3 CH 13 CII 3 Cil 3 Il 11 It Il H CH 3 il il il il il li ll HH 11 Il 3-C 1 4- Cl 4-Cl 4 Cl 4 Cl 4 Cl 3 4-Cl 3

  77) 42 68.57 57.29 57.29 59.07 60.64 68 1 69.84 70.94

  75564 68.99 51.6 53346 59 34 58> 61 64> $ 4 67 98 70.85

  6,909 5> 14 6:68 6 68 4.48 5 05 4.7

> 82 6) 4

6.39 5.78 5.67 5.52 5.03 5.24 5.3

63 6> 63

) 02 8.0 3.82 3 82 6.27 5 t 90 4.7

7.41 6.9

, 03 7> 87

3> 7 4.11 6.02 5.76 4, 5 617

6 J 96

  111-115 221-223 * 214-216 * 169-170 * 133-137 * 161-163 oil 189-191 * 151-156 * * =) Decompositio 11 u 4 Co TABLE (Continued) Elemental Analysis Carbon Hydrogen Nitrogen No Rl R 2 RY Calculated Found Calculated Found Found

  C-10 H H O 4-CH 77> 0 7692 5.7 5.9 5.3 5.05

  C-11 Ci 13 IO 4-CI 13 77 d 4 75 49 6> 1 6,14 50 4,89 C-12 H1 I O 4-OCH 3 72,6 70 Y 5,554 6.0 510 4) 8 C -13 Ci I 3 Ci 13 O 4-OCH 3 73.8 72 e 9 6.2 6.7 4.5 4.7 C-14 ** 1 O 3-CF 3 62.7 62.4 354 455 6 , 35 598 C 13 C 13 R 13 = R, R + = Cl 3 -CF 3 59 e 76 57.9 3.93 4.06 3.67 3.56 C-16 H HOY = 3-Cl, X = 4-C 1 60 e O 60.1 3.5 3 d 7 4.4 4.8 C-162 is 2-phenyl-3-oxo-4- (3,4-dichlorophenyl) -5-amino -2,3-dihydrofuran * = Decomposition

** = 4-NO 20-

Melting point, C

142-146 148-154

  138-141 1 140-143 3 oil oil 179-182 ru Ln 4 'n Co

Example 11

  In this example, the compounds of Table A were tested, respectively, using the procedures described below to determine their pre-emergence and post-emergence activity against various grasses and various broadleaf plants including

  a cultivated cereal and a broadleaf cultivated plant.

  The compounds used in the tests are identified by the number they bear in Table A above. Pre-emergent herbicidal test

  Pre-emergence herbicidal activity was determined as follows.

  Test solutions of the respective compounds were prepared as follows: 355.5 mg of the test compound was dissolved in ml of acetone. To the solution was added 2 ml of acetone containing 110 mg of a non-surfactant. Ionic 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.

  Seed of test vegetation was sown in a pot of soil and the test solution was applied uniformly by spraying on the earth's surface, at a dose of 27.5 micrograms / cm 2, or A few cases at the dose indicated in Table I below, some of the compounds being tested at a lower dose of 15.6 micrograms / cm 2 The pot was watered and installed in a greenhouse The pot was sprinkled intermittently seedling emergence, seedling vigor, etc., were observed for a period of 3 weeks. At the end of this period, the herbicidal efficacy of the compound was evaluated on the basis of physiological observations. scale from 0 to 100 where 0 represents the absence of phytotoxicity and 100 represents complete destruction. The results of these tests are reproduced in Table I. Post-emergence herbicidal test The test compound was formulated with as described above for the pre-emergence test This formulation was applied uniformly by spraying on two similar pots containing plants 5 to 7.6 cm high (except wild oat, soybean and soybean). panic pied-de-cock that had a height of 7.6 to 10.2 cm) (approximately

* 25 plants per pot) at a dose of 27.5 micrograms / cm 2.

  Once the plants were dry, they were placed in a greenhouse, then intermittently watered at their base, as needed. Plants were examined periodically for phytotoxic effects and physiological and morphological responses to treatment. At 3 weeks, the herbicidal efficacy of the compound was evaluated on the basis of these observations. A scale of 0 to 100 was used in which 0 represents the absence of phytotoxicity and represents complete destruction. The results of these tests are reproduced. on the table l I.

TABLE I

  Pre-emergence herbicide activity Application rate Plants: 27.5 micrograms / cm 2, unless otherwise specified Grasses Phytotoxicity,% Compound N 3 '4 to 7 ".8 to 9 to 1 t) 1 to 12 to 13 a 14 to 15 to 16 17 18 19 to 20 21 22 23 24 "1 25 26 Ch nopod 98 95 1 <O 1 () o 100

100 100 95

99

100 95

1 (10

98 90 95

  Phytotoxicity,% Mustard Re: knotted

100

10 (

100

100

100

o 100

100

100

100

100

100

100

1 (O 100

() 100

100

100

83 98

O O

100

100

25

100

1 (00

100

98 85

100

Soy

100 60 98

85

100 100 90 60 90 100 70 20 85 55

75

100 70 65

30 Panic Blood Panic Pied-de-Roq

100

100

1 () 0 80

100

70

1 (O 100

100

100

100

100

00 50

100

100

100

50

l O O 100

70

0 O

98,100

98 65

100

100

1 () 0

95

88

0 95

Wild oats

100 100

1 (O

  100 1 (O 100 100 100 60 1 (10 100 100 70 100 63

85

100 100 70 8 ()

o Rice 93

6 (75

85

7) 100 90 20 95 95 95

() 55 ()

() 80 100) 95 55 65 30

  r> 3 Ln l Co ", 1 a = proven at the rate of 15.6 microgranmes / cm 2 T A B L E A U I (Continued) Broadleaf plants Phytotoxicity,% Grasses Compound N

  27 28 29 30 31 32 33 34 35 36 37 38 39

41 42 43

44 45

46 47 48 49 50 51 52 53

goosefoot

99 98 98 100

95 10 () 1 () 100 100

100

100 95 100

100 100 100 60 100 100 100 100 60

Soya Nutty Mustard

98 97 55 100 80

100 100 100 100 100 100

100 100

100

100 55 65 100 100 100 100 65

lo

100 100 100 70

100

100 100 100 100

100

  100 100 100 60 30 100 100 100 100 50

o

98 25 80 25 78

100 100 85 100 70 100 50 25

15 93 70 30 75 100 100 98 100 35

Panic sanuin o 100 100

100 100 100

98 100 100 100 25

100 100 Panic pie of rooster

'55 100 80 80

100

'98 100

100 100 88 100

99 100

95 25 100 100 100 100 15

Phytotoxicity,% ed Wild oats o

55 95 60

(1) 0 O

100 100 100

70 25

100 100 Rice

10 () 15 80 75 78

I 1 () ()

1 t) () 88 100 65 IO O Il O <)

100 70)

93 100 100 95 1 (O O

  t) g rla um 4 n. Co, OD T A B L E A U I (Continued) Broadleaf Plants Phytotoxicity,% Compound N

54 55 56 57 58

59 6 (O

61 62 63

64 65 66 67 68 69

71 72 73 74 75 76 77 78

Kidopod)

100 100

98 100 1 (0) 10 Of) 100

  100 10 (100 (100 100 100) 100 100

Soy Knuckled Mustard 50

  100 100 45 100 100 100 45 100 100 100 100 100 98 95 95 100

100 99 93 99 98

100 75 '0 100 85 100

o O

  100 100 100 100 99 90 97 99 100 80 100 85 98 70 100

93 25 45

99 93 45

93 90 70

100 75

70 85

93 50

  85 100 Grasses Phytotoxicity,% Panic FootPanic blood of cock

100

73 20

100

65

100

15

100

100

94

20

100

100

95

100

100

100

100

100

100

100

100

100

100

10 (

100

100

Wild oats Rice

30 85

o

80 50

98,100

1 (O 99 100 95 100 93 98 98 99 94

100 90 ()

97 93 3 (

o

  85 90 (1 00 100 (85 95 93 9 93 I 0) 97 95 93 93 98 10 ()

  0% roa tn -4 n. TCO B A A L E A U I (Continued) Broadleaf Plants Phytotoxicity% Compound No

8 (81 to 82)

83 84 85

86 87 88 89 9)

91 92 93

94 95 96 97

goosefoot

80 100 99

100 100 100 100 100

99 20 93 Soy Knuckled Mustard

100 55

95 97

95

100 100 10 () 20

55 50 20

100 100 100

100 100

100 98

100 100

45 70 98 97

95

99 100 97 25

o Panic blood 100

100 100

90

100 100

  ramineae, hytotoxicity,% Panic pied-de-cock 1 (O 1 () () 1 t) O 10 ()

100 10 ()

  100 t () (l Ot 100 fl Ot F'olle oats) 2)

I () () 1 (1 (100

98 98

99 95 0

30 Rice t) () t) ()

97 97 75

  ti o 9 () 100 99 97 0 93 8 Y ear J n co -A

TABLE 1 A

  Comparative Compounds Herbicide Activity Pre-emergence Application Rate: 27.5 micrograms / cm 2, unless otherwise stated Lilly Plants Phtotoxicity% Compound N

C-1 C-2

  C-3 C-4 C 5 C-6 C-7 C-8 C-9 C-1 (C 11 C-12 C-13 C-14 C-15 C-16

  Lamb's-quarters 0oo 0) oo 30 o 0 ooo 0 Knotty mustard Soybean Grasshopper Grasses .r: otoxicity,% Cockroach 0 0 0 oooooo O o O oooooo Ooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooo 35 ooooo Q oo OO Wild oats oo 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 ooo () Rice 1) () OC) t) () U () () U () ()

U (I 0)

t) 0) 0) VI.4 -'j Cc -à

TABLE II

  Post-emergence herbicidal activity Application rate: 27.5 micrograms / yr 2, unless otherwise specified Lilly plants Phytotoxicity,% Compound N 3 Il 4 to 6 7 to 7 ,,) to 9 to 1 to 12 a 13 i 14 a I 5 a

16 17 183

  19 to 20) 21 22 23 24, to 25 Chenopode

85 70 60 80 60 95 65 8 () 9 () 90

1 i (O

80 80 65 35

o

43 50 8 (85 85 25

Mustard

100 90 95

80

100 95

n 100

9 () 90 95 73

8 () 3 (I 8 ()

* (

8 () 50

knotweed

92 75 75 70

98 65

90 90

90 80 60 35

o

60 70 90 75 N.T *

Soy 65

60 40

80 90 80 80

90 70 70 55 30

o

70 80

50 Bloodhopper 58

0 5 (J 30 45 80 40 70 30 30

30 50 20 7)

o o

60 70 40

  Grami i, s Phytotoxicity,% Panic Foot Cravings Oats

33 45

6 ()

0 or 65 65

30

60

90

65

90

0 3 t

20)

4 <) 5 <)

()

O

90

o O

) '75

O ()

(<) ()

0 0)

40

O ()

70

1 () 0 60)

O

O O

Rice 2) 42

() 2 <)

8 (Y 20)

6 () 20

  2 {) 0 20 2) t) o 1) 3) o O NT * = Not tested a = tested at 15.6 micrograms / cm 2 m Broadleaf plants Phytotoxicity,% TABLE II (Continued) ____ Grasses Phytotoxicity,% Compound N

  26 27 28 29 3 U 31 32 '33 34 35 36 37 3 U 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53

goosefoot

50 35 75 3) 7) 40 70 85

5 () 85 47 95

11 8) 25 75 50 70 60 75 85 50 95 30

Mustard 30

100 45

40 65

100 98

100 60

100

25 95

70 65

90 50

15 Knotty 35

45 80 35 42 85

70 45

40 98

10 75 25

50 70

80 90 40 95

Soya o 0 45 35 85

70 40

90 25 95

90 40 85 30 40 65

85 33

  Panic blood o 0 0 30 o 65 o o 45 0

40 25

80 30

o Panic piedde-rooster o 0 0 85 30 40

0 40 92 9 O 8 O

0 75

0 95 75

0 8 O

0 75 25 3 O 25 60 85 25 60

o o 40 O

92 90 80

O o 75 O

25 30 25 60 85 25

  O Wild oats -0 o 0 0 65 20 2 O 0 o

89 98 65

o 75 75 9 O 0 65 o 35

30 80 25 75

Rice 0 0) 52 () t 1 t)

60 75 35

() 65

0 95 31

o) O)

() 75 55

  o 25 ry tn 4 T-B A E II (Cont'd) Broadleaf Plants Phytotoxicity% Compound N

54 55 56 57 513 59 60

61 62

  63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78

Goosefoot 45

75 45

o 0 70 55

95 93 75 95 80 45 93

N.To *

90 85 90

Mustard

93 45 50

98 85 60

60 65

93 95 93 93 1 (O N.T *

85 100 98

Soybeans

73

0 O

90

70

65

0 O

80

90

70

0 O

75

55

(45

95

75

70

85

80

30

93

Panic blood

0 0 0 0 20 30 30

0 0 0 () 0 30 o 0 O n 93 75 o 25 30

25 25 20

  Grasses Phytotoxicity,%, Pied-bellied fox) () o 0

25 90 (O

o 2)

O 90 70

o

20 35 55

20 Wild oats l) o o 1) t)

1 () 3)

0 0 o () (O 9) O 75

10 35 45

2 ()

2 () 20

Rice o () o () 2) I) 1) () ()

() 20)

2) o 10 10 2 <) 25 () 20 () 85 85

80 75 75

  Ln L 4 co N.T * = not tested TABLE II (Continued) Broadleaf plants Phytotoxicity,% Grasses Compound N 8 (81 82

83 84 85 86

87,883 89

91 92 93 94 95 96 97

Lamb's goose

20 75 60 75 40 90

83 o

25 65

70 Soy Knuckled Mustard

20 98 25

30 40 65

65

98 70 98

20 65 70

35 75 45 45 35

55

50 85

o

20 65 70 65

93 20 80 30 85 40

30

85 88 83 75

o

20 40 55 55

Panic blood

6 O 0

O

63 45

20

0 55 25

  o o Phytotoxicity, Panic piedde-cock O

55 45

20 65

60 o 0 o Wild oats 0 65 o 0

40 35

o

10 90 70

o o 0 0 Rice 0 25

0 30 30

0 3 (10

c) o ON -J 4 n t s s

T AB L E TO IIA

  Propagative Activity Postemergence Herbicide Rate of Application: 27.5 micrograms / cman 2, unless otherwise specified. Loped Plants Phytotoxicity 6,% Compound N

C-I C-2 C 3 (C-4 C-5)

  C-6 f C-7 C (-8 C -9 C 1 () C-11 C-12 C-13

C-14 C-15 C-16

  Lamb's-quarters 2 (o o 0 0 0 0 0 o o o o o 25 o 25 o o o o Mustard 2 O 0 0 0

0 20 20 20 0 0 0 0

o o o o 0 25 O Retired

0 0 0 0 0

  o 0 25 10 o o o 0 o 0 o Soya o o o o o o o o o o o o o o o o 0 0 0 0 0 0 0 0 0 0 0

0 0 0 0 0 0 0 0

  0 O o o o o o o 0 0 o o o Grasses 0 o 0 o 0 o 0 o 0 0 0 0 o 0 0 0.0 0 0 O oo 0 o OO Wild oats o 0 0 0 0 0 0 0 0 0 0 0 0 0 U c.) 0 0 c) O 0 45 o Rice (J () O () 0 C) of Ln n Co As shown in Table I above, the compounds of the invention show in general a broad spectrum of excellent phytotoxic activity in pre-emergence and this is particularly the case of compounds Nos. 2, 4, 7, 9, 12, 14, 16, 22 Furthermore, as shown in Table II, the compounds also generally show a post-emergence phytotoxic activity against broadleaf plants and also in some cases against grasses, as is the case

  in particular compounds Nos. 7, 9, 12, 14, 16, 22 and 23.

  It can also be seen that the corresponding comparative compounds had a much lower activity than the corresponding compounds of the present invention.

  It goes without saying that the present invention has been described only for explanatory purposes, but in no way limiting and that many modifications can be made to it.

without leaving his frame.

Claims (10)

  A compound of formula: x R 1 (i) 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 halogen atoms independently selected from fluorine, chlorine, bromine and iodine; a haloalkyl group having 2 to 4 carbon atoms and 1 to 3 halogen atoms selected independently from fluorine, chlorine, bromine and iodine; a lower alkoxy group; lower alkylthio; lower alkoxyalkyl wherein the alkyl and alkoxy moieties independently have 1 to 3 carbon atoms; an alkylthioalkyl group whose alkyl portions have, independently, 1 to 3 carbon atoms; phenyl, naphth-1-yl, inden-1-yl, 4-fluorophenyl, arylalkylene having 1 to 3 carbon atoms in the alkylene portion and the aryl portion of which is phenyl, naphth-1-yl or indene-1 yl; or R is a substituted aryl group or a substituted arylalkylene group of formulas: R 4 R 5 R 4 R 5 - (R 3) - (R 3) R 6 R 9 or X Xfi R 4 R 5 - (R 3) I__ R; R 8 R 7   one, two or three of R, R, R, R 7, R and R are independently selected from the group consisting of lower alkyl, lower alkoxy, halogen, nitro or haloalkyl having 1 to 3 carbon atoms and 1 to 3 carbon atoms; with 3 equal or different halogen atoms, and the others are hydrogen atoms; and R is a single bond or an alkylene group having 1 to 3 carbon atoms; R 1 represents hydrogen or an alkyl group having 1 to 4 carbon atoms; R 2 is hydrogen, an alkyl group having 1 to 4 carbon atoms, alkenyl having 3 or 4 carbon atoms, lower alkoxycarbonylalkyl, lower alkoxyalkyl or lower alkylthioalkyl; 1 2   R and R together with the nitrogen atom to which they are attached form a saturated or unsaturated nitrogen heterocycle having 3 to 6 atoms, one of which is a nitrogen atom and the others are carbon atoms; X is hydrogen, lower alkyl, lower alkoxy, halo or trifluoromethyl and may occupy any position on the phenyl ring; and Y is a lower alkyl, lower alkoxy, halo, lower haloalkyl radical having 1 to 4 carbon atoms and 1 to 3 equal or different halogen atoms, a lower haloalkoxy radical having 1 to 4 carbon atoms and 1 to 3 halogen atoms, equal or different, or a lower halogenoalkylthio radical having 1 to 4 carbon atoms and 1 to 3 equal or different halogen atoms, provided that when Y is a halo radical, R, R and R 2 not all of them represent hydrogen and subject, moreover, that when Y represents something other than a trifluoromethyl radical, that X represents other than hydrogen and that R and R each represent a hydrogen atom, R then methyl, ethyl, propyl, 2-halophenyl, 2- (lower alkyl) phenyl or 4-fluorophenyl; and their compatible salts. 2 Compound of formula: X   F O (I) 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 halogen atoms independently selected from fluorine, chlorine, bromine and iodine; a haloalkyl group having 2 to 4 carbon atoms and 1 to 3 halogen atoms independently selected from fluorine, chlorine, bromine and iodine; a lower alkoxy radical, lower alkylthio; lower alkoxyalkyl, the alkyl and alkoxy portions of which have, independently, 1 to 3 carbon atoms; a lower alkylthioalkyl radical whose alkyl portions have, independently, 1 to 3 carbon atoms; phenyl, naphthyl, indene-1-yl, 4-fluorophenyl, an arylalkylene radical having 1 to 3 carbon atoms in the alkylene portion and wherein the aryl portion is a phenyl, naphth-1-yl or indene radical; -l-yl; or R is a substituted aryl or substituted arylalkylene group of formula: R 4 R 5 R 4 R 5 R 4 R 5 - (R 3) R 9 R R or R R 8 R 4 R 5 - (R 3) R 6 R R 7   one, two or three of R 4, R 5, R 6, R 7, R 8 and R 9 are independently selected from lower alkyl, lower alkoxy, halogen, nitro or halogenalkyl having 1 to 3 carbon atoms; and 1 & 3 halogen atoms or the like, and the others are hydrogen atoms; and R is a single bond or an alkylene group having 1 to 3 carbon atoms; R 1 is hydrogen or an alkyl radical having 1 to 4 carbon atoms; R 2 is hydrogen, an alkyl radical having 1 to 4 carbon atoms, alkenyl having 3 or 4 carbon atoms, lower alkoxycarbonylalkyl, lower alkoxyalkyl or lower alkylthioalkyl; R and R together with the nitrogen atom to which they are attached form a saturated or unsaturated nitrogenous heterocycle having 3 to 6 atoms, one of which is a nitrogen atom and the others are carbon atoms; X represents hydrogen or a lower alkyl, lower alkoxy, halo or trifluoromethyl radical and may occupy any position on the phenyl ring; and its compatible salts.   Compound according to claim 1 or 2, characterized in that R 1 or R 2 or preferably R 1 and R 2 are independently selected from hydrogen and methyl groups, ethyl and propyl.   Compound according to any one of Claims 1 to 3, characterized in that one of R 1 and R 2 is a methyl or ethyl group and the other is hydrogen,   a methyl group or an ethyl group, preferably hydrogen.   Compound according to any one of claims 1 to 4, characterized in that X is hydrogen.   Compound according to one of Claims 1 to 5, characterized in that R is a group   phenyl, naphthyl or substituted aryl, in particular a monosubstituted phenyl group such as a halophenyl group, or a lower alkylphenyl group, and especially a 4-fluorophenyl, 2halophenyl or 2- (lower alkyl) phenyl group, more particularly a 2-fluorophenyl group,   2-chlorophenyl or 2-methylphenyl.   Compound according to any one of claims 1 to 5, characterized in that R is lower alkyl, cycloalkyl, lower alkenyl, lower halogenoalkyl or lower halogenalkenyl, wherein R is   especially a methyl, ethyl or propyl radical.   Caposed according to claim 5 subordinate to claim 1, characterized in that Y is a radical   lower haloalkyl having 1 or 2 carbon atoms.   A herbicidal composition, characterized in that it comprises a herbicidally effective amount of a compound as claimed in any one of claims 1 to 8 or mixtures thereof, and a compatible carrier. A method for preventing or destroying vegetation, characterized by applying a herbicidally effective amount of a compound   according to any one of claims 1 to 8 or   mixtures of such a compound with foliage or with the future growth medium of said vegetation. Plant growth influencing composition, characterized in that it comprises an amount of a compound according to claim 1 or mixtures thereof, effective for modifying the growth pattern. Plant.   A process for influencing plant growth, characterized by applying to the foliage of said plants or their growth medium an amount of a compound according to claim 1, or mixtures of such compounds, effective to modify the growth pattern said plants.   The process for producing the compound according to claim 1, wherein R is phenyl, naphthyl-1-yl, indene-1-yl or substituted aryl as defined in claim 1, characterized in that it comprises corresponding compound of formula: Xo t CCHCCH 2 Zi X / CN (A)   wherein X and Y have the meanings given in claim 1 and Z "is the desired aryl or substituted aryl substituent R, in contact with a halogen selected from chlorine, bromine and iodine and a liquid carboxylic acid. under reactive conditions to produce the corresponding compound of formula I, said process being preferably carried out in an inert organic solvent at temperatures in the range of about 0 to 100 C and said halogen being bromine, the excess liquid carboxylic acid being especially used as said solvent inert organic.