CH659651A5 - 5-AMINO-3-OXO-4- (SUBSTITUTED-PHENYL) -2,3-DIHYDROFURANE, METHOD FOR THE PRODUCTION THEREOF AND HERBICIDES CONTAINING THESE COMPOUNDS. - Google Patents

Description

The present invention relates to compounds which have both herbicidal pre-emergence and herbicidal post-emergence activity and which in particular have good pre-emergence activity for a broad spectrum of broadleaved weeds and grass-like weeds. When used in small quantities, these compounds can also be used in agents for regulating plant growth.

The compounds according to the invention have the following formula

20th

p-

CHCCH-, 2 '

I.

CN

(A)

25th

(I)

30th

wherein X and Y are defined in claim 1 and Z 'corresponds to the desired R-aryl or substituted aryl substituent, is reacted with chlorine, bromine or iodine and a liquid carboxylic acid under reactive conditions, the corresponding compound of formula I being formed.

43. The method according to claim 42, characterized in that one carries out the reaction in an inert organic solvent at temperatures in the range from 10 to 100 ° C and that one reacts with bromine.

44. The method according to claim 43, characterized in that

that an excess of the carboxylic acid is used as an inert organic solvent.

40

The present invention relates to 5-amino-3-oxo-4- (substituted-phenyl) -2,3-dihydrofurans, to a process for their preparation, to a herbicidal composition which contains these compounds as active ingredient, and to a Plant growth regulating agent containing an amount of the herbicidally active compound effective to alter the growth of the plants. This invention also relates to a method for preventing or destroying the growth of plants and to a method for regulating plant growth using an effective amount of the new herbicidally active compound or compounds.

In Chemiker-Zeitung 104 (1980) No. 10, pages 302-303, the ring closure of l- (dimethylamino) -2,4-diphenyl-l-butene-3,4-dionezu5-dimethylamino-2,4-diphenyl was described -2,3-dihydro-furan. British Patent No. 1521092 mentions certain 3-phenyl-5-substituted 4 (1H) -pyridones or thiones as herbicides. In Japanese Patent Application No. 13710/69 (Chemical Abstracts 71: 61195e) the general formula for 5-amino-3-oxo-4- (phenyl and halophenyl) -2,3-dihydrofuran and especially for 5-amino-3- oxo-4- (phenyl and 4-chlorophenyl) -2,3-dihydrofurans. Japanese Patent Application No. 19090 (Chemical Abstracts 69P10352e) relates to certain 2,3-dihydrothiophenes used as pharmaceuticals

45

where R has the following meaning: lower alkyl with 1-4 carbon atoms, cycloalkyl with 3-7 carbon atoms, lower alkenyl, haloalkyl with 1-4 carbon atoms and 1-3 halogen atoms, independently of one another fluorine, chlorine, bromine and iodine, haloalkyl with 2-4 Carbon atoms and 1-3 halogen atoms, independently of one another fluorine, chlorine, bromine and iodine, lower alkoxy, lower alkylthio, lower alkoxyalkyl, in which the alkoxy and alkyl parts independently have 1-3 carbon atoms, alkylthioalkyl, in which the alkyl parts independently have 1-3 carbon atoms, Phenyl, naphth-l-yl, inden-l-yl, 4-fluorophenyl, arylalkylene with 1-3 carbon atoms in the alkyl portion and in which said aryl portion is phenyl, naphth-l-yl or inden-l-yl, or substituted aryl or substituted arylalkylene selected from the following group:

R4 .R5

50

55

60

65

- (R3) -;

R7 R6

or

659 651

R * R

- (R3) - (o \

A "'■

R8 R7

wherein one, two or three radicals R4, R5, R6, R7, R8 and R9 independently of one another are lower alkyl, lower alkoxy, halogen, nitro or haloalkyl having 1-3 carbon atoms and 1-3 identical or different halogen atoms and the remaining radicals are hydrogen and R3 represents a simple bond or an alkylene radical with 1-3 carbon atoms;

R1 is hydrogen or alkyl of 1-4 carbon atoms;

R2 is hydrogen, alkyl with 1-4 carbon atoms, alkenyl with 3 or 4 carbon atoms, lower alkoxycarbonylalkyl with preferably 1-4 carbon atoms in the alkoxy part and 1-4 carbon atoms in the alkyl part, in which the alkoxy and alkyl parts can independently have 1-3 carbon atoms or lower alkylthioalkyl or lower alkoxyalkyl, in which the alkyl moieties independently of one another preferably have 1-3 carbon atoms; or

R1 and R2 together with the nitrogen atom to which they are attached form a saturated or unsaturated nitrogen-containing heterocycle with 3-6 ring atoms, of which 1 ring atom is nitrogen and the remaining carbon atoms;

X represents hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl and can be in any position on the phenyl ring; and Y is lower alkyl, lower alkoxy, halogen, lower haloalkyl having 1-4 carbon atoms and 1-3 identical or different halogen atoms, lower haloalkalkoxy having 1-4 carbon atoms and 1-3 identical or different halogen atoms or lower haloalkylthio having 1-4 carbon atoms and 1-3 are identical or different halogen atoms, with the proviso that if Y is halogen then R, R1 and R2 are not all hydrogen and with the further proviso that if Y is different from trifluoromethyl and X has a meaning other than hydrogen, and R1 is hydrogen and R2 is hydrogen, then R is methyl, ethyl, propyl, 2-halophenyl, 2-lower alkylphenyl or 4-fluorophenyl.

The invention also relates to the tolerable salts of the compounds of the formula, e.g. B. on salts that can be obtained by replacing the hydrogen of the amino group (if R 1 and R 2 are hydrogen) with a compatible cation, or by enol formation of the 3-oxo group, followed by the replacement of the amino hydrogen .

The compounds of formula I exist as keto enol isomers. The compounds also have an asymmetric carbon atom and they can exist as optical isomers. In some cases, the compounds can also exist as geometric isomers. It is intended that the individual isomers as well as mixtures thereof as well as the specific isomers and also mixtures thereof be encompassed by the formula given above.

It was also discovered that the presence of a 3-trifluoromethyl substituent on the 4-phenyl group of the compounds of the invention causes a substantial increase in herbicidal activity.

In a further aspect, the present invention relates to a herbicidal composition which comprises a compatible carrier material and a herbicidally effective amount of a compound of the formula I or its tolerable salts. The herbicidal composition can also contain several of the active compounds according to the invention. The present invention also relates to a method for preventing or controlling the growth of an undesired vegetation by fertilizing the growth medium and / or the foliage of such vegetation with a herbicidally effective amount of at least one of the compound 10 of the formula I and / or treated their salts.

A further embodiment of the present invention relates to an agent for regulating plant growth which, together with a compatible carrier material, contains an amount which regulates plant growth and comprises at least one compound of the formula I or a salt thereof or mixtures of compounds of the formula I, in such a way Amount that they change the normal growth of the plants.

The present invention also provides a method for regulating plant growth, which is characterized in that the growth medium and / or the foliage of a vegetation to be treated is treated with such an amount of one or more compounds of the formula I and / or with compatible salts of which is effective to regulate normal plant growth.

The present invention also relates to a process for the preparation of the compounds of the formula I.

Typical compounds of the formula I according to the invention are listed in Examples 2, 3, 6-10 and below. Particularly preferred are those compounds in which R is lower alkyl, aryl or substituted aryl, and especially preferred are those compounds in which R is methyl, ethyl, propyl, phenyl or substituted phenyl, and above all R is phenyl, monomethylphenyl or monohalophene nyl, especially methyl, ethyl, n-propyl, 2-halophenyl, 2-lower alkylphenyl or 4-fluorophenyl; R1 and R2 are preferably independently of one another hydrogen, methyl, ethyl or n-propyl, and in particular one of the substituents R1 or R2 is hydrogen and the other is hydrogen, methyl, ethyl or n-propyl and in particular hydrogen, methyl or ethyl and above all Methyl; X is preferably hydrogen and / or Y in particular represents 3-trifluoromethyl or 3-halogen, but especially 3-trifluoromethyl. Most preferred are those compounds which have a combination of two or more preferred substituents.

The compounds of the formula I, in which R1 and R2 are both hydrogen and R is aryl or substituted aryl, are easily prepared by the following schematically illustrated reaction:

50 BC

55

25th

30th

35

40

45

Y CHCCHoZ

I.

CN

60

65

(A) ')

659 651

wherein X and Y are defined above and Z 'is aryl or substituted aryl.

The rearrangement of compounds of the formula A in the compound of the formula I 'is carried out according to the invention by contacting the compounds of the formula A with halogen, preferably with bromine, and a liquid carboxylic acid, usually in the presence of an inert organic solvent.

Typically, this process is carried out at temperatures in a range from 0 to 100 ° C, preferably at 20-30 ° C, and in particular it is reacted for about 3-36 hours, preferably about 18-24 hours, with about 1.0 to 10.0, preferably 1.0 to 1.1 moles of halogen per mole of compound A can be used. Suitable liquid carboxylic acids which can be used here are e.g. B. acetic acid, propionic acid, butyric acid, formic acid and the like. If an excess of the carboxylic acid is used, this excess can serve as a solvent or as a liquid carrier for this reaction system. Other organic solvents that can be used are e.g. B. liquid halogenated alkanes such. B. methylene chloride, carbon tetrachloride, chloroform, 1,2-dichloroethane; liquid aromatic compounds, such as B. benzene and toluene; liquid alkyl ethers, such as. B. diethyl ether, dimethyl, sulfoxide, dimethylformamide and the like as well as compatible mixtures thereof.

The best results are obtained using bromine, although chlorine and iodine could also be used.

The starting materials of formula A can be prepared according to the following reaction equation:

appropriate raw materials. The preparation of compounds of the formula Bistro. B. inOrg. Syn. Coll., Volume 1,107 (1941) and the preparation of the compound of formula C is disclosed in Org. Syn. Coll., Volume 1,270 (1941).

5 The compounds of the formula I, in which R1 and R2 each denote hydrogen, can be prepared by the general process which is shown schematically below:

10th

15

20th

25th

30th

&

CH2CN + 2'-CH2-C-ORj

(B) - (C)

(A)

35

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

This process can easily be carried out by reacting a compound of formula B with a compound of formula C and a strong base, preferably in an inert organic solvent.

Typically, this process can be carried out in a temperature range from about 0 to about 100 ° C, preferably at 75-85 ° C, one usually works for 5-36 hours, preferably 18-24 hours, and one uses about 0 to 10 hours. 0, preferably 1.0 to 1.2 moles of the compound of the formula C per mole of the compound B. Usually from about 1.0 to about 10.0 moles of the base are used per mole of the compound of the formula C.

Suitable strong bases that can be used are e.g. B. alkali metal alkanolates such. As sodium methoxide, sodium ethoxide, potassium ethoxide, sodium hydride, potassium hydride and the like. The strong base should preferably be one that does not form water as a by-product in this reaction system.

Suitable inert solvents that can be used are e.g. B. lower alkanols (e.g. methanol, ethanol and propanol), tetrahydrofuran, dimethoxyethane, dioxane and the like and compatible mixtures thereof. The alkali metal alkanolate is conveniently prepared in situ by reacting an alkali metal with the excess of an alkanol, which at the same time serves as a solvent for the reaction mentioned above.

The starting materials of the formulas B and C are generally known compounds, and they can be prepared by known methods or obtained by modifications of these methods, namely by the substi * (B)

r? 5

: H2CN + R-C-C-OR

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

This process can conveniently be carried out by reacting a compound of formula B with a compound of formula E and a strong base (e.g. sodium methoxide, sodium ethoxide), preferably in an inert organic solvent.

Typically, temperatures ranging from about 0-100 ° C, preferably 75-85 ° C, are used for this process and the process is carried out for 5-36 hours, preferably 18-24 hours, usually 0 to 10.0, preferably 1.0 to 1.2 moles of the compound of the formula E per mole of the compound of the formula B.

40 Suitable inert organic solvents that can be used here include. B. lower alkanols (e.g. methanol, ethanol, propanol, etc.); Tetrahydrofuran; Dimethoxyethane; Dioxane and the like, as well as compatible mixtures thereof.

45 Suitable bases which can be used for this process include the bases mentioned above with regard to the reaction of the compounds of the formula B with the compound of the formula C.

The hydroxy esters of formula E are in general

50 known compounds, and they can be prepared by known methods or by obvious modifications of these methods, e.g. B. using appropriate substituted starting materials.

The compounds of formula I, wherein R1 and R2 are hydrogen

55 are and R is alkyl, cycloalkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, arylalkylene, substituted arylalkylene or alkenylalkyl (e.g. -CH2CH = CH) can also be conveniently obtained by the processes shown schematically below:

60

i i t

+ Cyclizing agent

(A1)

659 651

i • i

(I''1)

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

This process can be carried out by reacting a compound of formula A 'with a cyclizing agent under reactive conditions, preferably in an inert organic solvent.

Typically, this process is carried out at a temperature range from about 0 to about 200 ° C, preferably at about 115 to 120 ° C. The reaction time is usually about 10-120 minutes, preferably about 10-30 minutes. Generally 1-10, preferably 1-2 moles of the cyclizing agent are used per mole of the compound of formula A '. Suitable cyclizing agents that can be used here include e.g. B. strong anhydrous acids such. B. sulfuric acid, hydrochloric acid, hydrobromic acid, trifluoroacetic acid, methanesulfonic acid and the like. The best results can be obtained using anhydrous sulfuric acid. Suitable inert organic solvents that can be used here are e.g. B. acetic acid, propionic acid, butyric acid, toluene, xylene and similar and compatible mixtures thereof.

The starting materials of formula A 'can be obtained according to the following reaction scheme:

/ J ^ -çhch2or

/ ■ cn i

(B *)

10th

(1)

/ - \ e®M, n

> (0Vc - c-ch2or10

/ cn y

(B11)

- c - ch - or

AAU 1 tutorial

10th

(a ')

wherein R "'and R10 are defined above, X' is chlorine, bromine or iodine and M and M 'are independently sodium or lithium.

Although three steps are shown schematically in this process, these steps are typically and conveniently performed in situ. It is also advantageous for such reactions that the reactions under essentially anhydrous conditions in the atmosphere of an inert gas such as e.g. B. nitrogen.

In the first stage of this process, the compound of formula B 'can be contacted with a non-nucleophilic base, preferably in an inert organic solvent. This step is typically carried out at temperatures in the range of about 0-25 ° C for about Vi to about 3 hours, using about 1-2, preferably about 1-1.3, mole equivalents of the non-nucleophilic base per mole of the compound of the formula B '. Suitable non-nucleophilic bases that can be used include e.g. Alkali metal-5 hydrides, such as B. sodium hydride, potassium hydride, etc.; Alkali metal amides, such as B. lithium bis (trimethylsilyl) amide; sodium bis (trimethylsilyl) amide; potassium bis (trimethylsilyl) amide; Lithium diethylamide, lithium diisopropylamide; Sodium di-methylamide and the like. In general, sodium hydride is preferred because it gives good results and the compound is readily available commercially. The alkali metal amides and, of course, the alkali metal hydrides are well known compounds and can be prepared by known methods or obvious modifications thereof. For example, the alkali metal amides can be obtained by reacting a secondary amine with an alkyl alkali metal.

Suitable inert organic solvents that can be used here are e.g. B. tetrahydrofuran, dioxane, dimethyl-20 oxyethane, diethyl ether, diisopropyl ether and the like and compatible mixtures thereof.

The second step of the process can be carried out by reacting the compound of the formula B "with an alkyl base, preferably in an inert organic solvent. As already mentioned above, this process step is preferably carried out in situ of the reaction product mixture of the first step. Typically, the second step is carried out at temperatures in the range of about -78 to 0 ° C for about 1-4 hours and about 1-2, preferably 1-1.3 mole equivalents of the alkyl base are used per mole of the compound of the Formula B ". Suitable alkyl bases that can be used are e.g. B. alkyl alkali metals, alkyl Grignard reagents and similar compounds. It is preferred to use n-butyllithium because it gives good results and is readily available commercially. Suitable solvents that can be used are u. a. those already mentioned above in the description of the first stage.

The third step can be carried out by reacting the compound of the formula B "'with the corresponding R" 40 halide which contains the desired group R' ", preferably by working in an inert organic solvent. The third reaction step is also typically performed in situ with the second stage reaction product mixture.

The third stage of this process can be carried out at temperatures in the range of about -30 to 30 ° C, preferably 22-25 ° C, reacting for about 1-18 hours, preferably 1-5 hours. In particular, about 1-10 moles, preferably 1-1.5 moles, of R "'X' 50 per mole of B" 'are used. Suitable inert organic solvents include those given in relation to the description of the first stage of this process, and similar solvents can also be used. The R '' 'X'-halides are well known compounds and can be made by known methods or by obvious modifications of these methods, e.g. B. by substitution of appropriate starting materials and solvents.

The starting materials of formula B 'can be prepared by the following schematic procedure:

25th

30th

45

60

ch2cn

(B)

R11OCCH2OR

(C)

10th

-> (B1)

wherein r11 is lower alkyl, preferably methyl and R10, Y and X have been defined above.

659 651

This process can be easily carried out by reacting a compound of formula B with a compound of formula C 'and a strong base under reactive conditions, preferably in an inert organic solvent.

Typically, this process is carried out using the same reaction conditions set forth above for the preparation of the compound of Formula A, except that the starting compound of Formula C 'is used in place of the starting compound of Formula C. The starting compounds of formula C 'are simple alkylalkoxyacetate esters, e.g. Methyl methoxy acetate. The manufacture of such a connection is generally well known.

The compound of the formula I in which one or both substituents R1 and R2 are substituted can be obtained by the alkylation of the amino group of the corresponding compounds of the formula I ":

+ R2 2 '1

(X ">

, 2V

(I '")

wherein R, R1, X and Y are defined above and R2 'is R2 but not hydrogen, and R2'Z "is an alkylating agent having the corresponding R2' or R 'group if dialkylation is desired .

This process can be carried out by reacting a compound of formula I "with a suitable alkylating agent capable of alkylating primary or secondary amino groups.

This implementation can B. be carried out by reacting a compound of the formula I "with an R2 iodide or bromide, preferably in an inert organic solvent and preferably in the presence of a base which absorbs the acid released. This process is preferably carried out at temperatures, which are in a range from about 0-100 ° C., preferably in a range from 20-45 ° C., and in particular one works for about 1.0-72, preferably 2.0-18 hours if the monalkylate is to be prepared , about 1.0 to 1.1 moles of the R2'-halide starting material are usually used per mole of the compound of the formula I ". If one intends to alkylate both amino hydrogen atoms, about 1.9 to 4, 0 moles of the R2'-halide can be used per mole of the compound of the formula I ". In those cases where it is desired to prepare a compound in which R2 'is alkoxyalkyl or alkylthioalkyl, a large excess of the R2'-halide, even if you only use a monoalkyl

desired; e.g. B. is used 3-6 moles of R2'Z "per mole of the compound of formula I". If desired, further alkylation can be carried out in a second stage. Variations can also be achieved with respect to the substituents R1 5 and R2 by first alkylating one of the two amino hydrogen atoms and then the second amino hydrogen atom with an alkylating agent which has a different R2 'group. Compounds in which R1 and R2 together with the amino nitrogen atom form a saturated heterocyclic ring can be prepared using the corresponding alkylating agent of the formula Z '' - (CH2) 2-5-Z '', in which Z '' Chlorine or bromine means. The R'R2N unsaturated heterocyclic ring can be prepared using an appropriate ice alkenyl dihalide, wherein one of the halogen atoms is located on each terminal carbon atom of the alkenyl chain. Suitable inert organic solvents that can be used include e.g. B. liquid halogenated alkanes such as methylene chloride, carbon tetrachloride or cichloroethane; Tetra-20 hydrofuran and similar solvents are also useful. Suitable bases for collecting the acid that can be used are e.g. B. those described in relation to the reaction of the compound of formula B with the compound of formula C.

25 Compounds of the formula I "', in which R1 is lower alkyl, for example methyl, and R2 is hydrogen or lower alkyl, are preferably prepared using dialkyl sulfate as the alkylating agent. This reaction can preferably be carried out by using the compound of the formula 30 in which one of the two substituents R1 and / or R2 is hydrogen, with the desired lower alkyl sulfate in the presence of a strong base and preferably in an inert organic solvent in the presence of a phase transfer agent.This process is typically carried out at temperatures which are in a range from about 0 to about 100 ° C., preferably at 20-45 ° C., using about 1.0 to 4.0 moles of the dialkyl sulfate per mole of the compound of the formula I. An excess of about 2.5 moles can be used The base is preferably carried out in an inert organic solvent such as methylene chloride, carbon tetrachloride oil, dichloroethane, tetrahydrofuran and similar solvents.

Suitable strong bases that can be used are e.g. B. sodium hydroxide, potassium hydroxide, sodium ethoxide, 43 sodium carbonate, potassium carbonate and similar bases. Suitable phase transfer agents are agents which transfer hydrophilic ions to a lipophilic organic medium, such as e.g. B. benzyltriethylammonium chloride, tetra-n-butylammonium chloride, methyltrioctylammonium chloride and the like. 50 The compatible salts of compounds of formula I can be prepared by known methods, for. B. by treating a compound of formula I, wherein R1 and / or R2 are hydrogen, with a suitable strong base, such as. B. n-Butyllithiu, sodium hydride, potassium hydride and the like-55, which contain the desired cation. Known methods can be used to obtain the corresponding R1 and / or R2 cationic salts. The enolate salts can be prepared by treating R1 and / or R2 cationic salts with a base according to known methods. Additional 60 variants for the production of cationic salts can be carried out using ion exchange resins which contain the desired cation.

In the processes described above, it is generally preferred to separate the individual products in the reaction sequence prior to proceeding to the next step, but with the exception if they are "in situ steps" or expressly stated otherwise . The products can be made from their corresponding reaction mixtures

659 651

be isolated by suitable separation methods and cleaning methods, such as. B. by recrystallization and chromatography. Suitable separation and cleaning methods are e.g. described in the examples below.

In general, the reactions mentioned above are carried out in the liquid phase, since pressure is generally not important, except that it has an effect on the temperature (boiling point) if the reactions are carried out under reflux. For this reason, the reactions can generally be carried out at pressures of about 300-3000 mm of mercury, and one usually works at about atmospheric pressure or at ambient pressure.

It should be noted that where typical or preferred reaction conditions (such as reaction temperatures, reaction times, molar ratios of starting compounds, solvents, etc.) have been given, other process conditions can also be used. The optimal reaction conditions (such as temperature, reaction time, molar ratios, solvents, etc.) can be varied depending on the starting compounds used or the organic solvents used, but it is possible to determine these optimal conditions by routine methods.

If mixtures of optically active isomeric compounds are obtained, the corresponding optically active isomers can be obtained by customary dissolution methods. Geometric isomers can be separated by known separation methods, which methods depend on the differences in physical properties between the geometric isomers.

Unless expressly stated otherwise, the following definitions have the following meanings:

The term "lower alkyl" refers to both straight chain and branched alkyl groups with 1-4 carbon atoms, including primary, secondary and tertiary alkyl groups. Typical lower alkyl residues include. B. methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl.

The definition «alkylene» refers to both straight-chain and branched alkylene groups and includes ch3 ~

"CH2 ~; ~ CH2 ~ CH2 ~ '-CH2CE2-

and similar groups.

The definition "lower alkenyl" refers to alkenyl groups with 2-6 carbon atoms, preferably with 2-4 carbon atoms and includes z. Vinyl, 1-propenyl, 2-propenyl, 1-methylvinyl, 1-butenyl, 2-methylprop-l-enyl and similar groups.

The term "lower alkoxy" refers to the groups of the formula -OR ', where R' is lower alkyl.

The definition "lower alkylthio" refers to the group of the formula -SR ', where R' is lower alkyl.

The term "lower alkoxyalkyl" refers to the group of the formula R'O "-, in which R 'and R" are independently straight-chain or branched alkyl groups having 1-3 carbon atoms.

The definition "lower alkylthioalkyl" refers to the group of the formula R'SR "-, in which R 'and R" independently of one another represent straight-chain or branched alkyl groups having 1-3 carbon atoms.

The definition “lower alkoxycarbonylakyl” refers to a group of the formula

R1 OCR "-

10th

wherein R 'is lower alkyl and R' 'means alkylene with 1-4 carbon atoms, which can be straight-chain or branched. Typical alkoxycarbonylalkyl groups include e.g. -CH2C (0) 0CH3; -CH (CH3) C (0) 0C2H5 and similar groups.

The definition «halogen» refers to fluorine, chlorine,

Bromine and iodine.

The definition “lower haloalkyl” refers to halogenalkyl compounds which have 1-4 carbon atoms and 1-3 halogen atoms, which are selected independently of one another from the group fluorine, chlorine, bromine and iodine. Preferably the lower haloalkyl group contains 1-2 carbon atoms.

The definition “lower haloalkoxy” refers to “lower alkoxy” groups with 1-3 halogen atoms, independently of one another being selected from the group consisting of fluorine, chlorine, bromine and iodine.

The term "aryl" refers to aryl groups with 6-10 carbon atoms and includes e.g. B. phenyl, naphthyl and indenyl. Typically the aryl radicals will be phenyl or naphthyl, and in particular compounds with these radicals are preferred because they are more readily available commercially than other aryl compounds.

The definition “substituted aryl” refers to aryl groups with 1-3 substituents, which independently of one another mean lower alkyl, lower alkoxy, halogen nitro or haloalkyl with 1-3 carbon atoms and 1-3 halogen atoms. Typical substituted aryl groups include e.g. B. 2-fluorophenyl, 2-chlorophenyl, 2,6-dimethylphenyl, 4-fluorophenyl, 2-methylphenyl, 2-chloro, 3-chloromethylphenyl, 2-nitro, 5-methylphenyl, 2,6-dichlorophenyl, 3- Trifluoromethylphenyl, 2-methoxyphenyl, 2-bromonaphth-l-yl, 3-methoxyinden-l-yl and the like.

The definition "arylalkylene" refers to the group of the formula ArR3-, where Ar is aryl and R3 is alkylene with 1-3 carbon atoms, and includes both straight-chain and branched-chain alkylene radicals, such as e.g. Methylene, ethyl, 1-methylethyl and propyl.

The term "(substituted aryl) alkylene" or "ring substituted arylalkylene" refers to the group of the formula Ar'R3-, where Ar 'is substituted aryl and R3 is alkylene as defined in relation to arylalkylene.

The term "saturated nitrogen heterocycle" as used here with respect to the substituents R1 and R2 of the formula I refers to a group of the formula:

45

1

A

!

S)

2 'n where n is 1, 2 or 3.

The definition “unsaturated, nitrogen-containing heteroxy-55 clic ring”, as used here in relation to the substituents R1 and R2 of the formula I, refers to groups which have the following formulas:

25th

30th

35

50

h2C

CH.

O

and

659 651 10

The definition of "tolerable salts" refers to salts, the substances that affect the leachability of the compound.

essentially remove the herbicidal properties of the parent compound and stabilize the soil.

not changed. Suitable salts include cationic agents. The agents according to the invention can also have various

Salts such as B. the cationic salts of lithium, sodium, their compatible additives, stabilizers, conditioning

Potassium, alkaline earth metals, ammonium, quaternary ammonium 5 agents, insecticides, fungicides and, if desired, other sodium salts and the like. contain herbicidally active compounds.

The definition “room temperature” or “ambient temperature. At reduced dosages, the temperature according to the invention” usually relates to a temperature range of compounds, an activity for regulating the plant

of about 20-25 ° C. Growing on and they can be used to do that

The compounds of the formula have both a herbicidal io growth to change green plants.

Pre-emergence and post-emergence activity, and they record. The compound of the formula I can be used as a means for regulating plant growth in pure form, in particular through a good herbicidal pre-emergence activity,

out. For the pre-emergence application you can use the herbicides but for the herbicidal application it is more practical to use them

To use compounds for the growth medium or for the future together with a carrier material. You can use the growth medium for the plant. The optimal 15 same types of carriers as used in relation to herbicides

Use the amount of herbicidal compound or herbicidal composition. Depending on the will depend on the particular plant cultivars and also the desired application, the agents for regulating the extent of plant growth and the particular plant growth can also have other compatible constituents.

Part of the plant with which the herbicidal compound or share, such as. B. desiccants, defoliants, top

herbicidal agents to be contacted. The optimal 20 surface active agents, other auxiliaries, fungicides and insect

Dosage is also included from the general location, the herbicides. Typically, the means of regulating

exercise, application (e.g. protected location, such as greenhouses, plant growth, a total of about 0.005

in contrast to exposed layers such as fields), the type and up to 90% by weight of at least one compound of the formula I

depend on the degree of control desired. In general, depending on whether the agent is used directly, one uses it both for the pre-emergence and for the 25 or whether it has to be diluted first. In the following,

Post-emergence control, about 0.02 to 60 kg / ha, preferably non-limiting examples and preparations

0.02 to 10 kg / ha of the active compounds present. the invention explained in more detail. Unless otherwise noted

Although it is theoretically possible to define all temperatures and temperature ranges in ° C

the undiluted, the compounds mentioned are ninned and the expression «ambient temperature» or «room temperature

Conveniently use in agents or formulations 30 mertemperature »refers to about 20-25 ° C. The definition det that an effective amount of at least one active compound "percent" or "%" refers to% by weight, and the expression, together with an acceptable carrier, ent- "mol" refers to gram-mole . The definition «equiva-

hold. An acceptable carrier (an agriculturally acceptable »refers to the amount of starting material used

carrier) is one which does not have any significant negative values in moles, with respect to the moles of before or after in the

Has an effect on the desired biological effects, 35 same example used reagent, which are caused by the active compounds, which can be weight or volume information. Where the carrier's only task is based on the dilution of the specified, the proton magnetic resonance spectra were active compounds. Typically, the composite (PMR or KMR) contain determined at 60 mHz. The signals are expressed as approximately 0.05 to 95% by weight of the compound of the sigletts (s), broad singletts (bs), doublets (d), double doubles

Formula I or mixtures of these compounds. There are 40 bletts (dd), triplets (t), double triplets (dt), quartets (q)

also the possibility of concentrates with higher concentration and multipletts (m); and cps refers to the ten manufacture, these concentrates are designed to be cycles per second. If necessary, examples were repeated

to be diluted before use. The carrier materials for additional starting material for the following examples can be solid or liquid, but they can also provide aerosols.

represent. The formulations can be in the form of granules, powders, dusts, solutions, emulsions, slurries.

genes, aerosols and in similar forms. example 1

Suitable solid supports that can be used include (3-trifluoromethylphenyl) benzylcarbonyl acetonitrile e.g. natural clay (such as: kaolin, attapulgite, in this example 4.91 g of metallic sodium was added to montmorillonite etc.), tallow, pyrophyllite, diatomaceous earth, pine 50110 ml of anhydrous ethanol at room temperature and stirred silky, artificial fine silica, calcium aluminosulicate , so long until all sodium was dissolved. A mixture of tricalcium phosphate and the like. There is the possibility of using 18.76 g (3-trifluoromethylphenyl) acetonitrile and 21.73 g of ethyl-likewise organic materials as support materials- phenylacetate was then added dropwise to the punched out, such as, for. B. Flour from walnut shells, casings of cotton - the mixture is added with stirring, heating about seeds, wheat flour, wood flour, flour from wood bark and the like - for 5518 hours at reflux. Then the loaned materials. Suitable liquid diluents, the resulting mixture added to 300 ml and extracted one can be used, e.g. Water, organic three times with ethyl ether. The pH of the aqueous solvent (such as, for example, hydrocarbons such as benzene, toluene, layer was adjusted to about 1 by adding aqueous, 10% by weight dimethyl sulfoxide, kerosene, diesel oil, heating oil, petroleum naphthalene hydrochloric acid and extracted again three times with tha etc.) as well as similar substances. Suitable aerosol carriers, the 60 ethyl ethers. The organic layer has been used twice with saturate, typically comprising common aerosols, aqueous sodium bicarbonate, washed over magnesium sol supports such as. B. halogenated alkanes etc. sulfate dried and evaporated to dryness in vacuo,

The agents can also be different accelerators and where m ^ n received 22.6 g of the title compound,

Contain surfactants that correspond to speed in a similar manner, by using the method of transporting the active compound into the tissue of the method described 65 above and by using

Accelerate plants, such as: organic solvents, the substituted phenylacetonitrile and ethyl-substituted phhe

Wetting agents and oils and in the case of agents that are used as nylacetates as starting materials, the following

the uses are intended as pre-emergence agents, such bonds are made:

(5-chloro-3-trifluoromethylphenyl) benzylcarbonyl acetonitrile;

(4-chloro-3-trifluoromethylphenyl) benzylcarbonyl acetonitrile;

(2-bromo-3-trifluoromethylphenyl) benzylcarbonyl acetonitrile;

(6-fluoro-3-trifluoromethylphenyl) benzylcarbonyl acetonitrile;

(4-methyl-3-trifluoromethylphenyl) benzyl carbonyl acetonitrile;

(5-methoxy-3-trifhiormethylphenyl) benzylcarbonyl aceto-nitrile;

(6-methyl-3-trifluoromethylphenyl) benzylcarbonyl acetonitrile;

(3,5-di-trifluoromethylphenyl) benzylcarbonyl acetonitrile;

(3-difhiormethoxyphenyl) benzylcarbonyl acetonitrile;

(3-trifluoromethoxyphenyl) benzylcarbonyl acetonitrile;

(3-trifluoromethylphenyl) - (4-fluorobenzylcarbonyl) acetonitrile;

(3-trifluoromethylphenyl) -l-naphthylmethylene-acetonitrile;

(2-chloro-3-methylphenyl) benzylcarbonyl acetonitrile;

(4-ethyl-3-methylphenyl) benzylcarbonyl acetonitrile;

(5-methoxy-3-chlorophenyl) benzylcarbonyl acetonitrile;

(3-iodophenyl) benzylcarbonyl acetonitrile;

(3-difhiormethylthiophenyl) benzylcarbonyl acetonitrile;

(3-trifluoromethylthiophenyl) benzylcarbonyl acetonitrile;

(3,5-diethoxyphenyl) benzylcarbonyl acetonitrile;

(3-bromophenyl) - (2-nitrobenzylcarbonyl) acetonitrile;

(2-chloro-3-methylphenyl) benzylcarbonyl acetonitrile;

(3-bromo-2-ethylphenyl) naphth-l-ylmethylene carbonyl ace-tonitrile;

(2,3-dimethylphenyl) beta-naphth-l-ylmethyl-carbonyl-ace-tonitrile;

(3-chlorophenyl) benzylcarbonyl acetonitrile;

(3-methylphenyl) benzylcarbonyl acetonitrile;

(3-t-butoxyphenyl) benzylcarbonyl acetonitrile;

(3-propylphenyl) benzylcarbonyl acetonitrile;

(3-bromophenyl) benzylcarbonyl acetonitrile;

(3-iodophenyl) - (3-nitrobenzylcarbonyl) acetonitrile;

(3-trifluoromethylphenyl) - (2,3-dichlorobenzylcarbonyl) acetonitrile;

(3-methoxyphenyl) -l-naphthylmethylene carbonyl acetonitrile;

(3-trifluoromethyl) - (3-chloro-8-fluofnaphth-l-ylmethylene carbonyl) acetonitrile;

(3-trifluoromethyl) - (3-chloro-8-fluoronaphth-l-ylmethylene carbonyl) acetonitrile;

(3-trifluoromethyl) - [(2-trifluoromethyl-3-methyl-8-methoxy-naphth-l-yl) methylene carbonyl] acetonitrile;

(3-trifluoromethyl) -inden-l-ylmethylene carbonyl) acetonitrile; and

(3-trifluoromethyl) - (2-fluoroinden-l-ylmethylene carbonyl) acetonitrile;

Example 2

2-phenyl-3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3-dihydrofuran

In this example, a solution containing 21.8 g (3-tiifluoromethylphenyl) benzylcarbonyl acetonitrile dissolved in 60 ml acetic acid is treated dropwise with a solution of 12.65 g bromine in 20 ml glacial acetic acid. The reaction mixture is stirred at room temperature for about 16 hours. The reaction mixture is then poured into 250 ml of water and the resulting mixture is extracted three times with ethyl ether. The organic extracts are washed with saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate and concentrated in vacuo to give 8.4 g of a white solid which is then dried to give 7.0 g of the title compound.

11 659 651

In a similar way, by adapting the method described above to compounds listed in Example 1, the following compounds can be prepared:

5

2-phenyl-3-oxo-4- (5-chloro-3-trifluoromethyl-phenyl) -5-amino-2,3-dihydrofuran;

2-phenyl-3-oxo-4- (4-chloro-3-trifluoromethylpheny]) - 5-amino-2,3-dihydrofuran; io 2-phenyl-3-oxo-4- (2-bromo-3-trifluoromethyl-phenyl) -5-amino-2,3-dihydrofuran;

2-phenyl-3-oxo-4- (6-fluoro-3-trifluoromethyl-phenyl) -5-amino-2,3-dihydrofuran;

2-phenyl-3-oxo-4- (4-methyl-3-trifluoromethyl-phenyl) -5-15 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-trifluoromethyl-phenyl) -5-amino-2,3-dihydrofuran; 20 2-phenyl-3-oxo-4- (3,5-di-trifluoromethyl-phenyl) -5-amino-2,3-dihydrofuran;

2-phenyl-3-oxo-4- (3-difluoromethoxyphenyl) -5-amino-2,3-di-hydrofuran;

2-phenyl-3-oxo-4- (3-trifluoromethoxyphenyl) -5-amino-2,3-di-25 hydrofuran;

2- (4-fluorophenyl) -3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3-dihydrofuran;

2- (l-naphthyl) -3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3-dihydrofuran; 30 2-phenyl-3-oxo-4- (2-chloro-3-methylphenyl) -5-amino-2,3-dihydrofuran;

2-phenyl-3-oxo-4- (4-ethyl-3-methylphenyl) -5-amino-2,3-di-hydrofuran;

2-phenyl-3-oxo-4- (5-methoxy-3-chlorophenyl) -5-amino-2,3-35 dihydrofuran;

2-phenyl-3-oxo-4- (3-iodophenyl) -5-amino-2,3-dihydrofuran;

2-phenyl-3-oxo-4- (3-difluoromethylthiophenyl) -5-amino-2,3-dihydrofuran;

2-phenyl-3-oxo-4- (3-trifluoromethylthiophenyl) -5-amino-2,3-40 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-di-hydrofuran;

45 2-phenyl-3-oxo-4- (2-chloro-3-methylphenyl) -5-amino-2,3-dihydrofuran;

2- (l-naphthyl) -3-oxo-4- (3-bromo-2-ethylphenyl) -5-amino-2,3-dihydrofuran;

2- (l-naphthyl) -3-oxo-4- (2,3-dimethylphenyl) -5-amino-2,3-50 dihydrofuran;

2-phenyl-3-oxo-4- (3-chlorophenyl) -5-amino-2,3-dihydro-furan;

2-phenyl-3-oxo-4- (3-methylphenyl) -5-amino-2,3-dihydro-furan;

55 2-phenyl-3-oxo-4- (3-butoxyphenyl) -5-amino-2,3-dihydro-furan;

2-phenyl-3-oxo-4- (3-butoxyphenyl) -5-amino-2,3-dihydro-furan;

2-phenyl-3-oxo-4- (3-propylphenyl) -5-amino-2,3-dihydro-60 furan;

2-phenyl-3-oxo-4- (3-bromophenyl) -5-amino-2,3-dihydro-furan;

2- (3-nirophenyl) -3-oxo-4- (3-iodophenyl) -5-amino-2,3-dihydrofuran;

65 2- (2,3-dichlorophenyl) -3-oxo-4- (3-trifluoromethyl-phenyl) -5-amino-2,3-dihydrofuran;

2- (l-naphthyl) -3-oxo-4- (3-methoxyphenyl) -5-amino-2,3-dihydrofuran;

659 651 12

2- (3-chloro-8-fluoronaphth-l-yl) -3-oxo-4- (3-trifluoromethyl-2-allyl-3-oxo-4- (3,6-dimethylphenyl) -5-amino-2 , 3-dihydro

phenyl) -5-amino-2,3-dihydrofuran; furan;

2- (2-trifluoromethyl-3-methyl-8-methoxy-naphth-l-yl) -3-oxo-2-trifluoromethyl-3-oxo-4- (3-trifluoromethyl) -4-bromophenyl) -

4- (3-trifluoromethylphenyl) -5-amino-2,3-dihydrofuran; 5-amino-2,3-dihydrofuran;

2-Inden-l-yl-3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3- 5 2- (2-chlorovinyl) -3-oxo-4- (3-nitro-4- methylphenyl) -5-amino-

dihydrofuran; and 2,3-dihydrofuran;

2- (2-fluoroinden-l-yl) -3-oxo-4- (3-trifluoromethylphenyl) -5- 2-methyl-3-oxo-4- (3-methoxyphenyl) -5-amino-2,3- dihydro

amino-2,3-dihydrofuran. furan;

2-methyl-3-oxo-4- (3-difluoromethylthiophenyl) -5-amino-2,3-

Example 3 10 dihydrofuran;

2-methyl-3-oxo-4- (3-trifhiormethylphenyl) -5-amino-2,3- 2-methyl-3-oxo-4- (3-trifluoromethylthiophenyl) -5-amino-2,3-

dihydrofuran dihydrofuran;

In a dry three-necked round bottom flask of 500 ml, 2-ethyl-3-oxo-4- (3-chlorophenyl) -5-amino-2,3-dihydrofuran;

with a mechanical stirrer, an additional dropper, 15 2-vinyl-3-oxo-4- (3-methylphenyl) -5-amino-2,3-dihydro-

funnel and a reflux condenser, 100 furan were added;

ml of ethanol. 3.5 g of 2-allyl-3-oxo-4- [3,5-di (trifluoromethyl) phenyl] -5-amino-2,3- were added to the stirred solvent.

Sodium added. After all the metal had dissolved, dihydrofuran;

there was a solution of 13.0 g of ethyl L - (+) - lactate and 8.5 gm-2-trifhiormethyl-3-oxo-4- (4-fluorophenyl) -5-amino-2,3-dihy-

Trifluoromethylphenyl acetonitrile in 30 ml ethanol dropwise 2Q drofuran;

to the reaction mixture. The mixture received a deep red 2- (2-chlorovinyl) -3-oxo-4- (2-bromophenyl) -3-oxo-5-amino-

Color, and after the addition was complete, the mixture was mixed on 2,3-dihydrofuran;

Reflux stirred overnight (about 18 hours). Then 2-propyl-3-oxo-4- (2-methoxy-3-chlorophenyl) -5-amino-2,3-

the mixture was cooled to room temperature and added to dihydrofuran;

300 ml of water, and the resulting mixture was washed with 10% 25 2-butyl-3-oxo-4- (2-chloro-3-fluorophenyl) -5-amino-2,3-dihy-

Chlorinated hydrochloric acid acidified (pH value about 1). Then drofuran;

the mixture was extracted with ether (three times) and the 2-vinyl-3-oxo-4- (3-chloro-4-methoxyphenyl) -5-amino-2,3-di-

organic extracts were washed with saturated aqueous sodium hydrofuran;

bicarbonate solution washed (twice), over magnesium sulfate 2-allyl-3-oxo-4- (3,5-dimethylphenyl) -5-amino-2,3-dihydro-

dried and concentrated in vacuo using a thick furan;

Got oil. This oil was mixed with ether / 2- (trifhiormethyl) -3-oxo-4- (trifluoromethyl-5-bromophenyl) -

Petroleum ether added, and the desired compound 5-amino-2,3-dihydrofuran;

crystallized in the form of a yellow powder. Two harvests of 2- (2-chlorovinyl) -3-oxo-4- (3-fluoro-4-methylphenyl) -3-oxo-5-

Crystals were collected to give a total of 4.7 g of amino-2,3-dihydrofuran;

Title link. Similarly, by further adapting the 35 2-phenyl-3-oxo-4- (3-methoxyphenyl) -5-amino-2,3-dihydro method described above and the corresponding furan;

substituted starting materials, the 2-methyl-3-oxo-4- (3,5-difluorophenyl) -5-amino-2,3-dihydro-

following compounds: furan;

2-ethyl-3-oxo-4- (3-trifhiormethylphenyl) -5-amino-2,3-dihy-2-vinyl-3-oxo-4- (3,5-diethylphenyl) -5-amino-2, 3-dihydro

drofuran; 40 furan;

2-ethyl-3-oxo-4- (5-chloro-3-trifluoromethylphenyl) -5-amino- 2-allyl-3-oxo-4- (3-propoxyphenyl) -5-amino-2,3-dihydro-

2,3-dihydrofuran; furan;

2-cyclopentyl-3-oxo-4- (3-trifhiormethylphenyl) -5-amino- 2-trifluoromethyl-3-oxo-4- (3-fluorophenyl) -5-amino-2,3-dihy-

2,3-dihydrofuran; drofuran;

2-vinyl-3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3-dihy- 45 2-propyl-3-oxo-4- (3-bromophenyl) -3-oxo-5-amino -2,3-dihy-

drofuran; drofuran;

2-allyl-3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3-dihy-2-phenyl-3-oxo-4- (2-iodo-3-fluorophenyl) -5-amino- 2,3-dihy-

drofuran; drofuran;

2-allyl-3-oxo-4- (2-methoxy-3-trifluoromethylphenyl) -5- 2-benzyl-3-oxo-4- (2-isoproxy-3-trifluoromethylphenyl) -5-

amino-2,3-dihydrofuran; 50 amino-2,3-dihydrofuran;

2-trifluoromethyl-3-oxo-4- (3-trifluoromethylphenyl) -5-amino- 2- (3-chlorophenyl) -3-oxo-4- (2,3-dimethylphenyl) -5-amino-

2,3-dihydrofuran; 2,3-dihydrofuran;

2-methyl-3-oxo-4- (3-difluoromethoxyphenyl) -5-amino-2,3-di-2-naphth-l-yl-3-oxo-4- (3-trifluoromethyl-4-bromophenyl) - 5-

hydrofuran; amino-2,3-dihydrofuran;

2-methyl-3-oxo-4- (3-trifluoromethoxyphenyl) -5-amino-2,3- 55 2- (3-methylphenyl) -3-oxo-4- (3-butyl: 4-methylphenyl) -3 -

dihydrofuran; oxo-5-amino-2,3-dihydrofuran;

2- (2-chlorovinyl) -3-oxo-4- (3-trifhiormethylphenyl) -5-amino- 2- (3-fluorophenyl) -3-oxo-4- (3-chlorophenyl) -5-amino-2, 3-di-

2,3-dihydrofuran; hydrofuran;

2- (2-chlorovenyl) -3-oxo-4- (5-propoxy-3-trifluoromethyl- 2- (2,3,5-trifluorophenyl) -3-oxo-4- (3-trifluoromethylphenyl) -5-

phenyl) -5-amino-2,3-dihydrofuran; 60 amino-2,3-dihydrofuran;

2-Methyl-3-oxo-4- (2-methoxy-3-chlorophenyl) -5-amino-2,3- 2- (3-methylnaphth-l-yÌ) -3-oxo-4- (3-trifluoromethylphenyl ) -5-

dihydrofuran; amino-2,3-dihydrofuran;

2-ethyl-3-oxo-4- (3-methoxy-3-chlorophenyl) -5-amino-2,3-di-2-chlorovinyl-3-oxo-4- (3-trifluoromethylphenyl) -5-amino- 2,3-

hydrofuran; dihydrofuran;

2-ethyl-3-oxo-4- (2-chloro-3-fluorophenyl) -5-amino-2,3-dihy-65 2-fluoromethyl-3-oxo-4- (3-trifluoromethylphenyl) -5-amino -

drofuran; 2,3-dihydrofuran;

2-vinyl-3-oxo-4- (3-methyl-4-methoxyphenyl) -5-amino-2,3- 2-methoxymethylene-3-oxo-4- (3-trifluoromethyl) -5-amino-2, 3-

dihydrofuran; dihydrofuran;

2-propoxymethylene-3-oxo-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-2,3-dihydrofuran;

2-methylthiomethylene-3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3-dihydrofuran; and

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

Example 4.

(3-trifluoromethylphenyl) methoxyacetyl acetonitrile

In this example, 5.6 g of metallic sodium was added to 120 ml of anhydrous ethanol at room temperature under a nitrogen atmosphere, and evolution of hydrogen occurred. After the evolution of hydrogen was completed, a mixture of 30 g of (3-trifluoromethylphenyl) acetonitrile and 18.5 g of methyl methoxyacetate in anhydrous ethanol was added, and the resulting mixture was refluxed for 3-4 hours. This mixture was then added to 300 ml of water and extracted three times with petroleum ether. The remaining aqueous phase was acidified to a pH of about 1 with 10% aqueous hydrochloric acid and extracted three times with ethyl ether. The ethyl ether extracts were combined, washed twice with a saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate and concentrated by evaporation. The concentrate 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 received in the form of a brown solid.

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

Example 5

(3-trifluoromethylphenyl) -2-methoxyisovaIeryI-acetonitrii

In this example, 10 g of (3-trifluoromethyl-phenyl) -methoxyacetyl-acetonitrile was added dropwise to a slurry of 1.87 g of sodium hydride in 20 ml of tetrahydrofuran, and the mixture was operated at a temperature of about 0 ° C under a nitrogen atmosphere until hydrogen was released developed. After it was found that the evolution of hydrogen had ceased, the mixture was cooled to a temperature of about -78 ° C. and 24.3 ml of 1.6 molar n-butyllithium in hexane were added dropwise. The mixture was stirred at a temperature of -78 ° C for 1-1.5 hours and then stirred at a temperature of about 0-4 ° C for 20 minutes. Then 3.9 ml (about 6.64 g) of 2-iodopropane was added dropwise and the mixture was stirred overnight (about 14-16 hours). This mixture was added to water, acidified with aqueous 10% hydrochloric acid, and extracted three times with ethyl ether. The extracts were combined, dried over magnesium sulfate and concentrated in vacuo to give 11.4 g of the title compound as an oil.

In a similar manner, by adapting the method described above, but using the corresponding alkyl, aryl or substituted aryl iodide, bromide or chloride instead of iodopropane, the following compounds can be prepared:

13 659 651

(3-trifluoromethylphenyl) - (2-methoxy-3-phenyl-propionyl) acetonitrile;

(3-trifluoromethylphenyl) - [2-methoxy-3- (2-fluorophenyl) propionyl] acetonitrile; 5 (3-trifluoromethylphenyl) - [2-methoxy-3- (3-methy] phenyl) propionyl] acetonitrile;

(3-trifluoromethylphenyl) - [2-methoxy-3- (2-ethoxyphenyl) propionyl] acetonitrile;

(3-trifluoromethylphenyl) - [2-methoxy-3- (3-nitro-phenyl) pro-10 pionyl] acetonitrile;

(3-trifluoromethylphenyl) - [2-methoxy-3- (2-trifluoromethylphenyl) propionyl] acetonitrile;

(3-trifluoromethylphenyl) - [2-methoxy-3- (chloro-3-propynyl) propionyl] acetonitrile; 15 (3-trifluoromethylphenyl) - [2-methoxy-3- (2-nitro-3-methoxyphenyl) propionyl] acetonitrile;

(3-trifluoromethylphenyl) - [2-methoxy-3- (2-fluoro-3-2 ', 2'-dichloroethylphenyl) propionyl] acetonitrile;

(3-trifluoromethylphenyl) - [2-methoxy-3- (2,3-dichloro-6-me-20thylphenyl) propionyl] acetonitrile;

(3-trifluoromethylphenyl) - (2-methoxy-4-phenylbutyryl) ace-tonitrile;

(3-trifluoromethylphenyl) - [2-methoxy-5- (2-bromophenyl) va-leryljacetonitrile;

25 (3-trifluoromethylphenyl) - (2-methoxy-3-methyl-4-phenylbu-tyril) acetonitrile;

(3-trifluoromethyl) - (2-methoxy-3-naphth-l-ylpropionyl) ace-tonitrile;

(3-trifluoromethyl) - [2-methoxy-3- (2-fluoronaphth-l-yl) propio-30 nyljacetonitrile;

(3-Trifhiormethyl) - [2-methoxy-3- (2-fluoronaphth-l-yl) propionylylacetonitrile;

(3-trifluoromethyl) - [2-methoxy-3- (3-butylnaphth-l-yl) propionyl] acetonitrile;

35 (3-trifluoromethyl) - [2-methoxy-3- (5-methoxynaphth-l-yl) propionyljacetonitrile;

(3-trifluoromethyl) - [2-methoxy-3- (6-nitronaphth-l-yl) propionyl] acetonitrile;

(3-trifluoromethyl) - [2-methoxy-3- (7-trifluoromethylnaphth-1-40 yl) propionyl] acetonitrile;

(3-trifluoromethyl) - [2-methoxy-3- (2-chloro-8-methylnaphth-l-yl) propionyl] acetonitrile;

(3-Trifhiormethyl) - [2-methoxy-3- (3-methoxy-5-nitro-7-fluoromethylnaphth-l-yl) propionyl] acetonitrile; 45 (3-trifluoromethyl) - (2-methoxy-4-naphth-l-ylbutryl) acetonitrile;

(3-trifluoromethyl) - [2-methoxy-5- (8-fluoronaphth-l-yl) valeryl] acetonitrile;

(3-trifluoromethyl) - [2-methoxy-3-methyl-3- (7-methoxy-50 naphth-l-yl) propionyl] acetonitrile;

(3-trifluoromethylphenyl) - (2-methoxy-3-inden-l-ylpropionyl) acetonitrile; and

(3-Trifluoromethylphenyl) - [2-methoxy-3- (2-fluoro-inden-l-yl) propionyl] acetonitrile.

55

In a similar manner, by adapting the method described above, but using other (mono- or disubstituted phenyl) - (methoxyacetyl) -acetonitrile instead of (3-trifluoromethylphenyl) -2-methoxyacetyl) 60 acetonitrile, the corresponding can be obtained mono- or disubstituted phenyl derivatives of the compounds listed above.

Example 6

65 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

659 651

14

Containing 7.8 g of concentrated sulfuric acid in 50 ml of acetic acid, heated to reflux for 30 minutes and then concentrated by evaporation in vacuo. The concentrate was mixed with diethyl ether, washed three times with normal aqueous sodium hydroxide, dried over magnesium sulfate and concentrated by evaporation to give an oil. This oil was triturated in 20 vol% ethyl acetate: 80% petroleum ether and allowed to stand overnight (14-16 hours). The solids were collected by filtration and washed three times with 20 vol% ethyl acetate: 80% petroleum ethyl to give 2.9 g of the title compound.

Similarly, by adapting the procedure described above, but using 3-tri-fluoromethylphenyldimethoxyacetyl acetonitrile prepared by the procedure of Example 1, as well as other products listed in Example 5, the following can be used Make connections:

2-methoxy-3-oxo-4 (3-trifluoromethylphenyl) -5-amino-2,3-di-hydrofuran;

2- (2-fluorobenzyl) -3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3-dihydrofuran;

2- (3-methylbenzyl) -3-oxo-4- (3-trifluoromethylphenyl) -5-amino-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-2,3-dihydrofuran;

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-2,3-dihydrofuran;

2- (2-nitro-3-methoxyphenyl) -3-oxo-4- (3-trifhiormethylphenyl) -5-amino-2,3-dihydroftirane;

2- (2-fluoro-3-2 ', 2'-dichloroethylbenzyl) -3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3-dihydrofuran;

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-trifhiormethylphenyl) -5-amino-2,3-dihydrofuran;

2- [l-methyl-2- (phenyl) ethyl] -3-oxo-4- (3-trifluoromethyl-phenyl) -5-amino-2,3-dihydrofuran;

2-naphth-l-ylmethylene-3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3-dihydrofuran;

2- (2-fluoronaphth-l-ylmethylene) -3-oxo-4- (3-trifluoromethylphenylene) -5-amino-2,3-dihydrofuran;

2- (3-butylnaphth-l-ylmethylene) -3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3-dihydrofuran;

2- (5-methoxynaphth-l-ylmethylene) -3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3-dihydrofuran;

2- (6-nitronaphth-l-ylmethylene) -3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3-dihydrofuran;

2- (7-trifluoromethylnaphth-l-ylmethylene) -3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3-dihydrofuran;

2- (2-chloro-8-methylnaphth-l-ylmethylene) -3-oxo-4- (3-tri-fluoromethylphenyl) -5-amino-2,3-dihydrofuran;

2- (3-methoxyy-5-nitro-7-fluoromethylnaphth-l-yl) -3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3-dihydrofuran;

2- (beta-naphth-l-ylmethyl) -3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3-dihydrofuran;

2- [beta- (8-fluoronaphth-l-yl) ethyl -] - 3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3-dihydrofuran;

2- [1- (7-methoxynaphth-l-yl) ethyl] -3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3-dihydrofuran;

2-indene-l-ylmethylene-3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3-dihydrofuran and

2- (2-fluoroinden-l-ylmethylene) -3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3-dihydrofuran.

5 Similarly, by adapting the procedure described above, but using the corresponding mono- and disubstituted analogues of the starting materials for the compounds mentioned above, the corresponding 4- (3-methylphenyl) -; 4- (3-beta-10 fluoroethoxyphenyl) -; 4- (3-difluoromethylene thiophenyl) -; 4- (3-chlorophenyl) -; Prepare 4- (2-bromo-3-trifluoromethylphenyl) - and 4- (2-methyl-3-difluoromethylene thiophenyl analogues of the compounds mentioned above.

15 Example 7

2-phenyl-3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-

2,3-dihydrofuran In this example, about 1 g of solid sodium hydroxide in 4.0 ml of water was added to a mixture of 3 g of 2-phenyl-3-oxo-4- (3-20 trifluoromethylphenyl) -5-amino-2, 3-dihydrofuran in 50 ml of methylene chloride at room temperature, and then 1.19 g of dimethyl sulfate and 0.11 g of benzyltriethylammonium chloride were added. The resulting two-phase mixture was stirred at room temperature for about 2 hours, then washed three times with water, dried over magnesium sulfate and finally concentrated by evaporation in vacuo. The residue obtained was then purified by chromatography on silica gel and eluting with mixtures of tetrahydrofiiran and chloroform, whereby the title compound was obtained. In a similar manner, by adapting the method described above, but using the products listed in Examples 2, 3 and 6 as starting materials, the corresponding 5-methylamino homologs could be prepared, such as:

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-trifhiormethylphenyl) -5-methylamino-2,3-dihydrofuran;

2-phenyl-3-oxo-4- (6-fluoro-3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran;

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-methyl-50 amino-2,3-dihydrofuran;

2-phenyl-3-oxo-4- (3-trifluoromethoxyphenyl) -5-methylamino-2,3-dihydrofuran;

2-phenyl-3-oxo-4- (3-trifluoromethoxyphenyl) -5-methylamino-2,3-dihydrofuran;

2-phenyl-3-oxo-4- (3-trifhiormethylthiophenyl) -5-methylamino-2,3-dihydrofuran;

2- (4-fluorophenyl) -3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran;

2- (l-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; 65 2-phenyl-3-oxo-4- (5-methoxy-3-chlorophenyl) -5-methylamino-2,3-dihydrofuran;

2-phenyl-3-oxo-4- (3-iodophenyl) -5-methylamino-2,3-dihydrofuran;

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2-phenyl-3-oxo-4- (3-trifluoromethylthiophenyl) -5-methylamino-2,3-dihydrofuran;

2-phenyl-3-oxo-4- (3-trifluoromethylthiophene) -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) -5-methylamino-2,3-dihydrofuran;

2-phenyl-3-oxo-4- (2-chloro-3-methylphenyl) -5-methylamino-2,3-dihydrofuran;

2- (l-naphthyl) -3-oxo-4- (3-bromo-2-ethylphenyl) -5-methylamino-2,3-dihydrofuran;

2- (l-naphthyl) -3-oxo-4- (2,3-dimethylphenyl) -5-methylamino-2,3-dihydrofuran;

2-phenyl-3-oxo-4- (3-chlorophenyl) -5-methylamino-2,3-dihydrofuran;

2-phenyl-3-oxo-4- (3-methylphenyl) -5-methylamino-2,3-di-hydrofuran;

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) -5-methylamino-2,3-dihydrofuran;

2- (2,3-dichlorobenzyl) -3-oxo-4- (2-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran;

2- (l-naphthyl) -3-oxo-4- (3-methoxyphenyl) -5-methylamino-2,3-dihydrofuran;

2- (3-chloro-8-fluoronaphth-l-yl) -3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran;

2- (2-trifluoromethyl-3-methyl-8-methoxynaphth-l-yl) -3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran;

2-inden-l-yl-3-oxo-4- (3-trifhiormethylphenyl) -5-methylamino-2,3-dihydrofuran;

2- (2-fluoroinden-l-yl) -3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran;

2-methyl-3-oxo-4- (3-trifluoromethylphenyi) -5-methylamino-2,3-dihydrofuran;

2-ethyl-3-oxo-4- (3-trifhiormethylphenyl) -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) -5-methylamino-2,3-dihydrofuran;

2-vinyl-3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran;

2-allyl-3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran;

2-allyl-3-oxo-4- (2-methoxy-3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran;

2-trifluoromethyl-3-oxo-4- (3-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- (2-chlorovinyl) -3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran;

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-chlorophenyl) -5-methylamino-2,3-dihydrofuran;

2-vinyl-3-oxo-4- (3-methyl-4-methoxyphenyl) -5-methylamino-2,3-dihydrofuran;

2-allyl-3-oxo-4- (3,6-dimethylphenyl) -5-methylamino-2,3-dihydrofuran;

2-trifluoromethyl-3-oxo-4- (3-trifluoromethyl-4-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-difluoromethylthiophenyl) -5-methylamino-2,3-dihydrofuran;

2-methyl-3-oxo-4- (3-trifluoromethylthiophenyl) -5-methylamino-2,3-dihydrofuran;

2-ethyl-3-oxo-4- (3-chlorophenyl) -5-methylamino-2,3-dihydrofuran;

2-vinyl-3-oxo-4- (3-methylphenyl) -5-methylamino-2,3-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-2,3-dihydrofuran;

2-propyl-3-oxo-4- (2-methoxy-3-chlorophenyl) -5-methylamino-2,3-dihydrofuran;

2-butyl-3-oxo-4- (2-chloro-3-fluorophenyl) -5-methylamino-2,3-dihydrofuran;

2-vinyl-3-oxo-4- (3-chloro-4-methoxyphenyl) -5-methylamino-2,3-dihydrofuran;

2-allyl-3-oxo-4- (3,6-dimethylphenyl) -5-methylamino-2,3-di-hydrofuran;

2-trifluoromethyl-3-oxo-4- (3-trifluoromethyl-5-bromophenyl) -5-methylamino-2,3-dihydrofuran;

2- (2-chlorovinyl) -3-oxo-4- (3-fluoro-4-methylphenyl) -3-oxo-5-methylamino-2,3-dihydrofuran;

2-phenyl-3-oxo-4- (3-methoxyphenyl) -5-methylamino-2,3-dihydrofuran;

2-methyl-3-oxo-4- (3,5-difluorophenyl) -5-methylamino-2,3-di-hydrofuran;

2-vinyl-3-oxo-4- (3,5-diethylphenyl) -5-methylamino-2,3-di-hydrofuran;

2-allyl-3-oxo-4- (3-propoxyphenyl) -5-methylamino-2,3-dihydrofuran;

2-trifourmethyl-3-oxo-4- (3-fluorophenyl) -5-methylamino-2,3-dihydrofuran;

2-propyl-3-oxo-4- (2-bromophenyl) -3-oxo-5-methylamino-2,3-dihydrofuran;

2-phenyl-3-oxo-4- (2-iodo-3-fluorophenyl) -5-methylamino-2,3-

dihy drofuran;

2-benzyl-3-oxo-4- (2-isoproxy-3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran;

2- (3-chlorophenyl) -3-oxo-4- (2,3-dimethylphenyl) -5-methylamino-2,3-dihydrofuran;

2-naphth-l-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-2,3-dihydrofuran; and

2- (3-methylnaphth-l-yl) -3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran;

2-chlorovinyl-3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran;

2-fluoromethyl-3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran;

2-methoxymethylene-3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran;

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2-propoxymethylene-3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran;

2-ethoxymethylene-3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran;

2- (2-methoxyprophyl) -3-oxo-4- (3-trifhiormethylphenyl) -5-methylamino-2,3-dihydrofuran;

2-methylthiomethylene-3-oxo-4- (3-trifhiormethylphenyl) -5-methylamino-2,3-dihydrofuran and

2- (l-propylthioethyl) -3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran;

2-benzyl-3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran;

2- (2-fluorobenzyl) -3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran;

2- (3-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-2,3-dihydrofuran;

2- (4-fluorobenzyl) -3-oxo-4- (3-trifhiormethylphenyl) -5-methylamino-2,3-dihydrofuran;

2- (2-trifluoromethylbenzyl) -3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran;

2- (chloro-3-propylphenyl) -3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran;

2- (2-nitro-3-methoxyphenyl) -3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran;

2- (2-Fiuor-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- (beta-phenethyl) -3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran;

2- [3- (2-bromophenyl) propyl] -3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran;

2- [l-methyl-2- (phenyl) ethyl] -3-oxo-4- (3-trifhiormethylphenyl) -5-methylamino-2,3-dihydrofuran;

2-naphth-l-ylmethylene-3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran;

2- (2-fluoronaphth-l-ylmethylene) -3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran;

2- (3-butynaphth-l-ylmethylene) -3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran;

2- (5-methoxynaphth-l-ylmethylene) -3-oxo-4- (3-trifhioromethylphenyl) -5-methylamino-2,3-dihydrofuran;

2- (6-nitronaphth-l-ylmethylene) -3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran;

2- (7-trifluoromethylnaphth-l-ylmethylene) -3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran;

2- (2-chloro-8-methylnaphth-l-ylmethylene) -3-oxo-4- (3-tri-fluoromethylphenyl) -5-methylamino-2,3-dihydrofuran;

2- (3-methoxy-5-nitro-7-fluoromethylnaphth-l-yl) -3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran;

2-methoxy-3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran;

2- (betan-naphth-l-ylethyl) -3-oxo-4- (3-trifhiormethylphenyl) -5-methylamino-2,3-dihydrofuran;

2- [beta- (8-fluoronaphth-l-yl) ethyl] -3-oxo-4- (3-trifluoromethyl-phenyl) -5-methylamino-2,3-dihydrofuran;

2- [1- (7-methoxynaphth-l-yl) ethyl] -3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran;

2-inden-l-ylmethylene-3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran and

2- (2-fluoroinden-l-ylmethylene) -3-oxo-4- (3-trifluoromethylphenyl) -5-methylamino-2,3-dihydrofuran:

Similarly, by approximately doubling the amount of dymethylsulfate and increasing the reaction time, the corresponding 5-dimethylamino homologs of the compounds listed above can be prepared. Similarly, using diethyl sulfate instead of dimethyl suphatate, the corresponding 5-ethylamino and 5-diethyl-5 amino homologues of the compounds mentioned above can be obtained.

Example 8

io 2- (2-fluorophenyl) -3-oxo-4- (3-triflourmethylphenyl) -5-allyl-amino-2,3-dihydrofuran

One gram of sodium hydroxide in 4.0 ml of water was added to a mixture of 4.0 g of (2- (2-fluorophenyl) -3-oxo-4- (3-trifluoromethylphenyl) -5-amino-2,3- dihydrofuran in 80 ml of methylene-15 chloride at room temperature, followed by the addition of 1.44 g of allyl bromide and 0.27 g of benzyltriethylammonium chloride The resulting two-phase mixture was stirred at room temperature for about 18 hours, after which time it was washed three times with water, dried over magnesium sulfate and concentrated in vacuo, the residue obtained was purified by chromatography on silica gel and eluting with chloroform to give 2.5 g of the title compound.

Similarly, applying this procedure to the products listed in Examples 2, 3 and 6, 25 the corresponding 5-allylamino analogs can be obtained. Similarly, by approximately doubling the amount of allyl bromide and sodium hydroxide, the corresponding 5-diallylamino analogs of the compounds can be obtained.

Similarly, using ethyl bromide 30 instead of allyl bromide, the corresponding 5-ethylamino and 5-diethylamino analogs can be prepared.

Similarly, using the same procedure using methoxymethyl bromide, ethylthiomethyl bromide, methyl bromoacetate, methyl 2-bromo-35 butyrate, l, 5-dibromopentane and cis-l, 4-dibromobut-l, 3-diene instead of alkyl bromide, the corresponding 5-methoxymethylamino, 5-ethylthiomethylamino, 5-methoxycarbonylmethylamino, 5- (l-methoxycarbonylpropylamino), 5-piperidin-l-yl and 5-pyrrol-l-yl analogs of the products were obtained, which are given in 40 Examples 2, 3 and 6, such as:

2-phenyl-3-oxo-4- (3-trifluoromethylphenyl) -5-methoxymethylamino-2,3-dihydrofuran;

2-methyl-3-oxo-4- (3-trifluoromethylphenyl) -5-methoxymethylamino-2,3-dihydrofuran; 43 2-ethyl-3-oxo-4- (3-trifluoromethylphenyl) -5-methoxymethylamino-2,3-dihydrofuran;

2-phenyl-3-oxo-4- (3-trifluoromethylphenyl) -5-ethylthiomethylamino-2,3-dihydrofuran;

2-methoxy-3-oxo-4- (3-trifluoromethylphenyl) -5-ethylthiome-50thylamino-2,3-dihydrofuran;

2-methyl-3-oxo-4- (3-trifluoromethylphenyl) -5-ethylthiomethylamino-2,3-dihydrofuran;

2-ethoxymethylene-3-oxo-4- (3-trifluoromethylphenyl) -5-ethylthiomethylamino-2,3-dihydrofuran; 55 2-ethyl-3-oxo-4- (3-trifluoromethylphenyl) -5-ethylthiomethylamino-2,3-dihydrofuran;

2-phenyl-3-oxo-4- (3-trifhiormethylphenyl) -5-methoxycarbonylmethylamino-2,3-dihydrofuran;

2-methyl-3-oxo-4- (3-trifluoromethylphenyl) -5-methoxycarbo-60 nylmethylamino-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; 65 2-phenyl-3-oxo-4- (3-trifhiormethylphenyl) -5- (l-methoxycarbonylprop-l-yl) amino-2,3-dihydrofuran;

2-methyl-3-oxo-4- (3-trifluoromethylphenyl) -5- (l-methoxy-carbonylprop-l-yl) amino-2,3-dihydrofuran;

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2-fluoro-3-oxo-4- (3-trifluoromethylphenyl) -5- (l-methoxycarbonylprop-l-yl) amino-2,3-dihydrofuran;

2-ethyl-3-oxo-4- (3-trifhiormethylphenyl) -5- (l-methoxycar-bonylprop-l-yl) amino-2,3-dihydrofuran;

2-naphth-l-yl-3-oxo-4- (3-trifluoromethylphenyl) -5- (l-methoxoxycarbonylprop-l-yl) amino-2,3-dihydrofuran;

2-indene-l-yl-3-oxo-4- (3-trifluoromethylphenyl) -5- (l-methoxycarbonylprop-l-yl) amino-2,3-dihydrofuran;

2-phenyl-3-oxo-4- (3-trifluoromethylphenyl) -5-piperidin-l-yl-2,3-dihydrofuran and

2-phenyl-3-oxo-4- (3-trifhiormethylphenyl) -5-pyrrol-l-yl-2,3-dihydrofuran, etc.

Similarly, using the procedures described above and using the 5-methyl-amino compounds of Example 7 as starting materials, the corresponding 5- (N-methyl-N-allylamino) -, 5- (N-methyl-N- ethylamino) -, 5- (N-methyl-N-methoxymethylamino) -, 5- (N-methyl-N-ethylthiomethylamino) -, 5- (N-methyl-N-methoxycarbonylmethylamino) - and 5- (N- Methyl-N-I'-me-thoxycarbonylpropylamino) analogs.

Example 9

Lithium salt of 2-phenyl-3-oxo-4- (3-trifluoromethylphenyl) -5-

methylamino-2,3-dihydrofuran (R --CH3, R -Li)

In this example, 5.4 ml of 1.6 molar n-butyllithium in hexane was added dropwise to a stirred solution containing 2.86 g of 2-pheny] -3-oxo-4- (3-trifluoromethy] phenyl) -5 -amino-2,3-dihydrofuran contained in 25 ml of tetrahydrofuran; the temperature was -30 ° C. The resulting mixture was stirred for 20 minutes and then concentrated in vacuo to give 2.8 g of the title compound as a light brown solid. Elemental Analysis: Calculated: C-63.74; H-3.84; N-4.13; found: C-61.82; H-4.90; N-3.48.

In a similar manner, with adaptation of the method described above, the corresponding lithium salts of the compounds of Examples 2-5 can also be prepared.

15 Example 10

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

20th

poses.

Table A

Elemental analysis

No. R1

R2

R

Carbon ber. Gef.

Hydrogen Ber. Gef.

Nitrogen calc. Gef.

Melting point in ° C

1

h h

0 **

63.95

64.66

3.76

4.19

4.39

4.78

182-184 *

2nd

ch3

H

0

64.86

64.22

4.20

4.65

4.20

3.79

154-155

3rd

ch3

ch3

0

65.71

65.63

4.61

4.83

4.03

4.12

102-106

4th

ch2ch3

H

0

65.71

66.55

4.61

5.12

4.03

3.98

143-145

5

ch2ch3

ch2ch3

0

67.20

67.76

5.33

5.63

3.73

3.77

115-120

6

h h

4-f0

60.53

59.66

3.26

3.47

4.15

4.12

136-138

7

ch3

H

2-f0

61.54

61.22

3.70

3.62

3.99

4.45

151-156

8th

ch3

ch3

2-f0

62.47

62.95

4.11

4.38

3.84

4.08

91-93

9

ch2ch3

H

2-f0

62.47

60.36

4.11

4.11

3.84

4.02

136-138

10th

(ch2) 2ch3

H

2-f0

63.32

63.6

4.49

4.7

3.69

3.71

53-60

11

CHoch3

ch2ch3

2-f0

64.12

63.41

4.83

4.93

3.56

3.85

01

12

ch3

H

2-c10

58.78

58.52

3.54

3.63

3.81

4.05

201-204 *

13

ch3

ch3

2-c10 *

59.77

59.67

3.93

4.05

3.67

3.72

116-119

14

ch, ch3

H

2-c10

59.77

60.5

3.93

4.05

3.67

3.89

131-137

15

ch2ch3

ch2ch3

2-c10

61.55

61.72

4.64

4.79

3.42

3.77

113-114

16

h h

2-ch30

64.86

65.02

4.20

4.43

4.20

4.28

179-181 *

17th

h h

3-ch30

64.86

62.54

4.20

4.27

4.20

3.82

148-151

18th

h h

4-ch30

64.86

65.86

4.20

4.25

4.20

4.34

208-211 *

19th

h h

2-cf30

55.81

55.58

2.84

3.05

3.62

3.69

68-75

20th

h h

3-cf30

55.81

55.37

2.84

3.09

3.62

3.40

60-63

21st

h h

2,6-diF0

57.46

57.45

2.82

3.14

3.94

4.16

225-227 *

22

ch3

H

2,6-diF0

58.54

59.3

3.25

3.45

3.79

3.84

191-193 *

23

ch2ch3

H

2,6-diF0

59.53

60.11

3.66

4.00

3.66

3.71

63-65

24th

-ch, ch = ctl h

2-f0

63.66

62.4

3.98

4.31

3.71

4.27

01

25th

h h

ch3

56.03

56.54

3.89

4.22

5.45

5.52

129-130

26

-CHoc (c1) = ch2

H

0

61.0

57.9

3.8

3.9

3.55

3.2

01

27th

-ch, ch = c (c1) ch3

H

0

61.8

61.3

4.2

4.7

3.4

3.1

134-138

28

-ch (ch3) coo & h5

H

0

63.0

61.5

4.8

5.0

3.3

3.2

01

659 651 18

Table A (continued) Elemental Analysis

carbon

hydrogen

nitrogen

Melting point

No.

R1

R2

R

Ber.

Gef.

Ber.

Gef.

Ber.

Gef.

iti ° C

29

Li

-ch3

0

63.74

61.82

3.84

4.9

4.13

3.48

120 *

30th

h h

1-naphthyl

68.3

65.8

3.8

4.1

3.8

3.8

123-126

31

ch3

H

1-naphthyl

68.9

65.7

4.18

4.4

3.7

3.55

174-179

32

ch3

ch3

1-naphthyl

69.5

69.2

4.5

4.7

3.5

3.6

139-143

33

h h

H

54.32

54.91

3.29

3.54

5.76

5.42

145-146 *

34

ch3

h h

56.03

55.75

3.89

4.04

5.45

5.39

158-159

35

ch3

h ch3

57.56

58.87

4.43

4.66

5.17

5.32

116-118

36

ch2ch3

h ch3

58.95

59.35

4.91

5.04

4.91

5.34

141-142

37

h h

ch2ch3

57.56

60.08

4.43

4.91

5.17

5.47

173-174

38

ch3

h ch2ch3

58.95

59.59

4.91

5.12

4.91

5.17

138-139

39

h h

(ch2) 2ch3

58.95

60.26

4.91

5.19

4.91

5.08

165-168

40

ch3

H

(ch2) 2ch3

60.20

61.2

5.35

5.84

4.68

4.56

01

41

ch3

ch3

(ch2) 2ch3

61.34

61.82

5.75

6.11

4.47

4.46

01

42

h h

ch (ch3) 2

58.95

58.79

4.91

5.23

4.91

5.0

155-156

43

ch3

h ch (ch3) 2

60.20

60.80

5.35

5.36

4.68

4.85

121-122

44

h h

(ch2) 3ch3

60.20

61.42

5.35

5.68

4.68

4.9

137-138 *

45

ch3

H

(ch2) 3ch3

61.34

62.84

5.75

6.17

4.47

5.03

90

46

ch3

H

Cyclohexyl

63.72

64.41

5.90

6.18

4.13

3.6

143-145

47

ch2ch3

H

Cyclohexyl

64.59

64.94

6.23

6.87

3.97

4.11

142-143

* =

decomposition

0 ** = phenyl, e.g.

B. 2-C10 = 2-chlorophenyl 0 *

= Phenyl,

e.g. 2,6-diF0

= 2,6-difluorophenyl

Table B

Elemental analysis

Carbon hydrogen nitrogen melting point

No.

R1

R2

R

Y

Ber.

Gef.

Ber.

Gef.

Ber.

Gef.

in ° C

48

h h

2-ch30

Cl

68.11

68.64

4.67

4.97

4.67

4.96

175-177

49

h h

2-f0

cl

63.26

62.3

3.62

3.8

4.61

4.17

178-180 *

50

ch3

H

2-c10

Cl

61.08

62.21

3.87

4.06

4.19

4.33

185-193 *

51

ch3

h h

Cl

59.07

59.1

4.48

4.95

6.27

6.24

117-120 *

52

ch2ch3

h h

Cl

60.64

61.11

5.05

5.52

5.90

6.03

177-178

53

h h

ch3

Cl

59.07

57.16

4.48

4.5

6.27

5.73

158-159

54

ch3

h ch3

Cl

66.64

62.11

5.05

5.42

5.90

6.05

119-122

55

h h

ch2ch3

Cl

60.64

58.69

5.09

5.46

5.89

5.67

152-155

56

ch3

h ch, ch3

Cl

62.03

63.34

5.61

5.83

5.56

5.96

95-97

57

ch3

ch3

ch2ch3

Cl

63.28

62.48

6.07

6.86

5.27

5.93

01

58

ch2ch,

h ch2ch3

Cl

63.28

63.82

6.7

6.52

5.27

5.89

120-123

59

h h

(ch2) 2ch3

Cl

62.03

62.13

5.61

5.76

5.56

5.63

152-154

60

ch3

H

(ch2) 2ch3

Cl

63.28

63.58

6.07

6.49

5.27

5.86

01

61

ch2ch3

H

(ch2) 2ch3

Cl

64.40

65.34

6.49

7.11

5.01

5.33

104-106

62

ch3

ch3

(ch2) 2ch3

Cl

64.40

64.14

6.49

6.65

5.01

4.67

01

63

h h

ch2 (ch3) 2

ci

62.04

63.69

5.57

6.05

5.57

6.37

156-157

64

ch3

h ch2 (ch3>

Cl

63.29

63.03

6.03

6.72

5.27

5.62

58-91

65

CHich->

h ch, (ch3),

Cl

64.41

65.66

6.44

6.83

5.01

5.47

130-131

66

h h

0

Br

58.20

54.8

3.64

3.79

4.24

3.97

177-178 *

67

ch3

H

0

Br

59.32

60.79

4.07

4.36

4.97

3.93

181-185

68

ctlch3

H

0

Br

60.35

61.01

4.47

4.74

3.91

3.53

161-163

69

h h

2-c10

Br

52.69

54.59

4.02

3.26

3.48

4.14

202-204

70

ch3

H

2-c10

Br

53.91

53.77

3.44

3.47

3.70

3.69

205-207

71

ch, ch3

H

2-c10

Br

55.05

55.3

3.82

3.97

3.57

3.51

144-147

72

h h

2-f0

Br

55.19

55.14

3.16

3.57

4.02

3.94

190-191.5

73

ch3

H

2-f0

Br

56.37

58.0

3.59

3.41

3.87

4.51

172-173

19 659 651

Table B (continued)

Elemental analysis

carbon

hydrogen

nitrogen

Melting point

No.

R1

R2

R

y

Ber.

Gef.

Ber.

Gef.

Ber.

Gef.

in ° C

74

ch2ch3

H

2-f0

Br

57.46

57.59

3.99

4.31

3.72

3.57

157-159

75

h h

2-ch30

Br

59.32

58.48

4.07

4.22

4.07

4.03

165-167

76

ch3

H

2-ch30

Br

60.35

60.36

4.47

4.68

3.91

3.96

208 -210

77

ch, ch3

H

2-ch30

Br

61.31

62.98

4.84

5.16

3.76

4.24

140-142

78

ch3

h h

Br

49.21

48.01

3.73

4.41

5.23

5.06

109-118

79

ch2ch3

h h

Br

51.08

50.35

4.26

4.28

4.97

4.86

172-175 *

80

h h

0

ch3

77.0

76.3

5.7

5.9

5.3

5.1

137-141

81

ch3

H

0

ch3

77.4

77.1

6.1

6.4

5.0

5.1

150-152

82

h h

0

och3

72.6

73.7

5.4

6.6

5.0

5.1

141-144

83

ch3

H

0

och3

73.2

72.5

5.8

5.9

4.7

3.6

128-133

84

ch3

H

0

och (ch3) 2

74.30

70.02

6.5

6.47

4.33

4.21

185-188 *

85

ch2ch3

H

0

och (ch3) 2

74.25

75.88

6.87

7.23

4.15

4.23

111-113

86

h h

2-ch30

och (ch3) 2

74.28

73.58

6.55

6.85

4.33

4.17

149-151

87

ch3

H

2-ch30

och (ch3) 2

74.75

74.35

6.82

6.95

4.15

3.83

134-135

88

ch2ch3

H

2-ch30

och (ch3) 2

75.19

73.63

7.17

7.27

3.99

4.19

134-136

89

h h

2-f0

och (ch3) 2

69.71

70.7

5.54

5.74

4.28

4.25

150-151

90

ch3

H

2-f0

och (ch3) 2

70.37

69.66

5.91

6.1

4.10

4.25

191-193

91

h h

2-c10

och (ch3) 2

66.38

68.29

4.07

4.36

5.28

5.48

171-173

92

h h

ch3

och (ch3) 2

68.0

65.75

6.9

6.6

5.7

5.6

151-155

93

ch3

h ch3

och (ch3) 2

68.69

68.69

7.28

8.01

5.36

6.15

114-115

94

h h

0

-00

76.95

76.3

5.0

6.0

4.1

3.0

73-78

95

ch3

ch3

0

-00

77.3

73.9

5.3

5.6

3.9

4.1

163-167

961

ch3

ch3

0

y = c1, x = c1

62.1

62.9

4.3

4.7

4.0

4.0

133-137

97

-ch2 (-ch2)

-ch2

0

-cf3

67.55

72.4

4.8 5

5.1

3.75

3.8

105-111

* Decomposition 961 is 2-phenyl-3-oxo-4- (3,4-dichlorophenyl) -5-dimethylamino-2,3-dihydrofuran

Table C Comparative Link

X

Elemental analysis

Carbon hydrogen nitrogen melting point

No.

r1

r2

r y

Ber.

Gef.

Ber.

Gef.

Ber.

Gef.

in ° C

c- 1

ch3

ch3

0

H

77.42

75.64

6.09

6.39

5.02

5.03

111-115

c- 2

h h

h h

68.57

68.99

5.14

5.78

8.0

7.87

221-223 *

c- 3

h h

H

3-c1

57.29

51.6

6.68

5.67

3.82

3.7

214-216 *

c- 4

h h

H

4-c1

57.29

53.29

6.68

5.52

3.82

4.11

169-170 *

c- 5

ch3

h h

4-c1

59.07

59.34

4.48

5.03

6.27

6.02

133-137 *

c- 6

ch3

ch3

H

4-c1

60.64

58.61

5.05

5.24

5.90

5.76

161-163

c- 7

ch3

H

0

4-c1

68.1

64.4

4.7

5.3

4.7

4.5

01

c- 8

h h

H

4-ch3

69.84

67.98

5.82

5.63

7.41

6.7

189-191 *

c- 9

ch3

h h

4-ch3

70.94

70.85

6.4

6.63

6.9

6.96

151-156

c-10

h h

0

4-ch3

77.0

76.2

5.7

5.9

5.3

5.05

142-146

c-ll ch3

H

0

4-ch3

77.4

75.49

6.1

6.14

5.0

4.89

148-154

c-12

h h

0

4-och3

72.6

70.5

5.4

6.0

5.0

4.8

138-141

c-13

ch3

ch3

0

4-och3

73.8

72.9

6.2

6.7

4.5

4.7

140-143

c-14

**

H

0

3-cf3

62.7

62.4

3.4

4.5

6.35

5.8

01

c-15

ch3

ch3

r = 0,

3-cf3

59.76

57.9

3.93

4.06

3.67

3.56

01

r = c1

c-162

h h

0

y = 3-c1, x = 4-c1

60.0

60.1

3.5

3.7

4.4

4.8

17 9-182

* = Decomposition ** = 4-NO20- 162 is 2-phenyl-3-oxo-4- (3,4-dichlorophenyl) -5-amino-2,3-dihydrofuran

659 651 20

Example 11 and observed over a 3 week period

In this example, the compounds of Table A, the visibility of the seedlings, the health of the seedlings and the compounds shown in Table B, etc. became visible. At the end of this period and also the comparison compounds listed in Table C, the herbicidal activity of the compounds was reduced.

estimates their pre-emergence and post-emergence activity against a 5 based on physiological observations. Man

Range of grasses and broad-leaved plants, including used a scale that ranged from 0-100. 0 means none of grain harvesting and harvesting broad-leaved plants, under-phytotoxicity, 100 means complete killing. She's looking for. The compounds tested are in Tables A, B. The results of these tests are in Table I below

and C identified. compiled.

10th

Pre-emergence herbicide test Post-emergence herbicide test

Pre-emergence herbicidal activity was assessed as follows. The test compounds were formulated in the same manner.

Determined way. as described above for the pre-emergence test.

Test solutions of the appropriate compounds were made up. These formulations were uniformly prepared in two similar ways, as follows: 15 pots were sprayed containing plants approximately 5.1-7.6 cm

355.5 mg of the test compound was dissolved in 15 ml of acetone. Were too high (apart from wild oats, soybeans and paspalium this solution was given 2 ml of acetone, the 110 mg of a nonionidilatatum, which were 7.6-10.2 cm high) (about 15-25 plants

contained surfactants. 12 ml of these bases per pot), with doses of 27.5 micrograms /

solution was then added to 47.7 ml of water, which used the cm2. After the plants were dry, they were given the same nonionic surfactants with a concentration in a greenhouse and then in between, so contained tration of 625 mg / 1. often it was necessary to water. The plants were raised periodically

Seeds of the test vegetation were planted in a pot with soil for their phytotoxic effects as well as their physiological and physiological effects, and the test solution was sprayed uniformly on the morphological reactions observed during the treatment.

Surface of the earth, taking care of a dosage of 27.5 25. After 3 weeks, the herbicidal activity was assessed

Micrograms / cm2 used; in some cases, such as the connection speed based on these observations. Following Table I, certain scales were used that ranged from 0-100. 0 meant none

Compounds tested at a low dose, namely phytotoxicity and 100 meant complete killing. The one with 15.6 micrograms / cm2. The pot was watered and one of the results of these tests are shown in Table II below

Given greenhouse. The pot was watered in between, put together.

Table I

Herbicidal pre-emergence activity Amount used: 27.5 micrograms / cm2 unless otherwise stated

broad-leaved plants

Grasses

Connect

% Phytotoxicity

% Phytotoxicity

dung

Chenopodi-

mustard

Amaranthus

soy

Digitaria

Paspalium

Savage

rice

No.

for album

retroflexus beans sanguinalis dilatatum

oats

1

94

100

100

95

100

100

100

93

2nd

100

100

100

100

100

100

100

100

3a

98

100

100

60

100

80

100.

60

4a

95

100

100

98

100

100

100

75

5

100

80

100

20th

100

70

100

20th

6

100

100

100

85

100

100

100

85

T

100

100

100

100

100

100

100

100

8a

98

100

100

100

100

100

100

70

9a

100

100

100

100

100

100

100

100

10th

100

100

100

90

100

100

100

90

lla

90

50

100

60

100

50

60

20th

12a

100

100

100

90

100

100

100

95

13a

100

100

100

100

100

100

100

95

14a

100

100

100

70

100

100

100

95

15a

95

90

100

20th

100

50

70

0

16

100

100

100

85

100

100

100

95

17th

99

83

98

55

100

70

63

55

18th

0

0

0

0

0

0

0

0

19a

100

80

100

20th

98

100

100

90

20th

100

100

100

75

98

65

85

50

21st

95

90

25th

40

100

100

100

80

22

100

100

100

100

100

100

100

100

23

100

100

100

70

100

100

100

95

24a

98

90

100

65

100

95

70

55

25th

90

98

85

90

100

88

80

65

26

95

75

100

30th

0

95

0

30th

No.

27th

28

29

30th

31

32

33

34

35

36

37

38

39

40

41

42

43

44

45

46

47

48

49

50

51

52

53

54

55

56

57

58

59

60

61

62

63

64

65

66

67

68

69

70

71

72

73

74

75

76

77

78

79

80

81

82

83

84

85

659 <

rice

0

45

100

15

80

75

78

100

100

100

70

100

88

100

65

0

100

10th

100

70

0

93

100

100

95

100

0

97

0

80

40

90

0

97

93

30th

0

60

85

90

100

100

85

95

93

99

100

97

95

93

93

98

100

0

0

0

0

97

97

75

21st

Table I (continued)

Herbicidal pre-emergence activity

Application rate: 27.5 micrograms / cm2, unless otherwise stated broad-leaved plant grasses

% Phytotoxicity% phytotoxicity

Chenopodi-

mustard

Amaranthus

soy

Digitaria

Paspalium

Wilder around album

retroflexus beans sanguinalis dilatatum

oats

0

0

0

0

0

0

0

99

98

100

45

99

48

67

98

97

100

98

100

100

90

98

55

100

25th

78

55

55

100

100

100

80

100

100

95

95

80

100

25th

100

80

60

95

100

70

78

98

80

90

100

100

100

100

100

100

100

100

100

100

100

100

100

100

100

100

100

100

100

100

100

100

100

100

85

98

98

98

100

100

100

100

100

100

100

100

100

100

70

100

100

100

100

100

100

100

100

100

100

100

100

100

50

100

100

100

95

100

100

25th

35

88

10th

100

100

100

100

100

100

100

90

100

100

15

98

99

75

100

100

100

93

100

100

100

100

100

100

70

100

100

90

100

55

60

30th

100

95

70

60

65

30th

75

25th

25th

25th

100

100

100

100

100

100

100

100

100

100

100

100

100

100

100

100

100

98

100

100

100

100

100

100

100

100

100

100

60

65

50

35

0

15

0

100

100

100

93

100

100

100

55

50

0

25th

73

20th

0

100

100

100

100

100

100

100

98

100

100

45

100

65

30th

100

100

75

90

100

100

85

50

45

0

0

60

15

0

100

100

100

99

100

100

100

100

100

85

93

100

100

80

100

100

100

45

100

94

50

25th

45

0

0

20th

20th

0

98

100

100

93

100

100

95

100

100 "

100

90

100

100

100

100

100

100

70

100

95

98

100

100

100

100

100

100

100

100

100

100

100

100

100

100

100

98

99

75

100

100

99

100

95

90

90

100

100

100

100

90

97

70

100

100

95

100

100

99

85

100

100

100

100

100

100

100

100

100

93

100

100

80

93

100

100

98

100

99

100

50

100

100

98

100

93

85

90

100

100

99

100

99

98

85

100

100

94

100

98

70

90

100

100

100

100

100

100

100

100

100

100

25th

20th

0

0

95

25th

10th

100

100

100

100

100

100

100

80

55

20th

45

98

25th

20th

100

100

100

70

100

100

100

99

95

100

98

100

100

100

100

97

100

97

100

100

99

100

100

100

85

100

100

90

659 651

22

Table I (continued)

Herbicidal pre-emergence activity

Application rate: 27.5 micrograms / cm2 unless otherwise stated

Connection no.

broad-leaved plants% phytotoxicity Chenopodi mustard around album

Amaranthus retroflexus

Soybeans

Grasses

% Phytotoxicity

Digitarla sanguinalis

Paspalium dilatatum

Wild oats

rice

87

100

95

100

95 '

99

100

98

80

88

100

100

100

90

100

100

98

90

89

100

100

100

99

100

100

100

100

90

100

100

100

100

100

100

99

99

91

99

100

100

97

100

100

95

97

92

20th

20th

0

25th

0

0

0

0

93

100

100

100

100

100

100

100

93

94

75

55

98

0

90

30th

0

0

95

100

100

100

55

100

100

75

40

96

93

50

100

0

100

60

30th

0

97

100

100

100

70

100

100

99

80

a = tested at 15.6 micrograms / cm2

Table IA comparative compounds

Herbicidal pre-emergence activity Amount used: 27.5 micrograms / cm2 unless otherwise stated

broad-leaved plants

Grasses

Connect

% Phytotoxicity

% Phytotoxicity

dung

Chenopodi-

mustard

Amaranthus

soy

Digitarla

Paspalium

Savage

rice

No.

for album

retroflexus beans sanguinalis dilatatum

oats

C- 1

40

25th

40

0

75

0

0

0

C- 2

0

0

0

0

0

0

0

0

C- 3

0

0

0

0

0

0

0

0

C- 4

0

0

0

0

0

0

0

0

C- 5

0

0

0

0

0

0

0

0

C- 6

0

0

0

0

0

0

0

0

C- 7

0

0

0

0

0

0

0

0

C- 8

30th

25th

0

40

0

0

0

0

C- 9

0

0

0

0

0

0

0

0

C-10

0

0

0

0

0

0

0

0

C-ll

0

0

0

0

30th

0

0

0

C-12

0

0

0

0

0

0

0

0

C-13

0

0

0

0

0

0

0

0

C-14

0

0

0

0

45

35

0

0

C-15

0

0

0

0

0

0

0

0

C-16

0

0

0

0

0

0

0

0

Table II Post-emergence herbicidal activity Application amount: 27.5 micrograms / cm 2, unless otherwise stated broad-leaved plant grasses

Connect% phytotoxicity% phytotoxicity Chenopodi mustard Amaranthus soybean Digitarla Paspalium wild rice

No. around album retroflexus beans sanguinalis dilatatum oats

1 60 100 50 50 40 33 45 20

2 85 100 92 90 58 60 60 42

3a 70 90 75 65 0 0 0 0

No.

4a

5

6

T

8a

9a

10th

lla

12a

13a

14 =

15a

16

17th

18th

19a

20th

21st

22

23

24s

25th

26

27th

28

29

30th

31

32

33

34

35

36

37

38

39

40

41

42

43

44

45

46

47

48

49

50

51

52

53

54

55

56

57

58

59

60

61

62

45

0

20th

80

20th

60

0

20th

20th

0

40

0

20th

0

0

0

0

0

0

30th

0

0

0

0

0

52

0

0

0

45

60

75

35

0

65

0

95

30th

0

45

0

0

0

15

0

75

55

0

25th

0

0

0

0

0

0

0

0

10th

0

23

Table II (continued)

Herbicidal post-emergence activity

Application rate: 27.5 micrograms / cm2, unless otherwise stated broad-leaved plant grasses

% Phytotoxicity% phytotoxicity

Chenopodi-Mustard Amaranthus Soy- Digitaria Paspalium Wilder around album retroflexus beans sanguinalis dilatatum oats

60

95

75

80

50

65

65

80

90

70

60

30th

30th

30th

60

80

60

40

45

60

60

95

100

98

100

80

80

90

65

100

65

80

40

65

65

80

95

90

90

70

90

90

90

100

90

80

30th

0

30th

90

90

90

80

30th

20th

20th

100

100

90

90

90

40

50

90

100

90

90

30th

50

0

80

90

90

70

50

80

90

80

90

80

70

20th

0

0

65

95

60

55

70

80

75

35

73

35

30th

0

0

0

0

0

0

0

0

0

0

55

45

45

0

55

45

40

43

80

45

33

0

0

0

50

30th

60

50

30th

0

0

80

80

70

70

60

90

70

85

100

90

80

70

100

60

85

80

75

65

40

35

0

25th

50

N.T. *

50

0

0

0

40

55

60

45

0

0

0

50

30th

35

0

0

0

0

35

40

0

0

0

0

0

75

100

100

80

70

85

65

30th

45

45

45

10th

30th

20th

70

80

80

70

30th

40

20th

40

40

35

35

0

0

0

70

65

42

50

35

40

60

85

100

85

85

80

92

89

100

100

100

100

100

90

98

75

98

70

70

65

80

65

50

50

45

40

0

0

0

85

100

100

70

75

75

75

47

60

40

0

0

0

0

95

100

98

80

95

95

95

90

100

90

90

45

75

75

11

0

10th

25th

0

0

0

80

100

75

95

90

80

90

25th

25th

25th

20th

0

0

0

75

95

90

90

55

75

65

50

50

50

40

20th

25th

0

70

70

70

85

40

30th

35

60

65

30th

30th

25th

25th

25th

75

90

80

40

60

60

30th

85

90

90

65

80

85

80

50

50

40

60

30th

25th

25th

95

100

95

85

60

60

75

30th

15

0

33

0

0

0

60

87

75

73

35

40

0

0

0

0

0

0

0

0

55

93

70

90

0

0

0

30th

45

85

70

0

0

0

45

50

30th

65

0

0

0

0

0

0

0

0

0

0

75

98

80

80

20th

20th

5

75

85

80

90

30th

25th

10th

45

60

60

70

0

0

30th

659 651

24th

Table II (continued)

Herbicidal post-emergence activity

Application rate: 27.5 micrograms / cm2 unless otherwise stated

Connection no.

broad-leaved plants% phytotoxicity Chenopodi mustard around album

Amaranthus retroflexus

Soybeans

Grasses

% Phytotoxicity

Digitaria sanguinalis

Paspalium dilatatum

Wild oats

rice

63

0

0

0

0

0

0

0

0

64

70

80

65

75

0

0

0

0

65

55

60

40

55

0

0

0

0

66

50

65

50

45

0

0

0

0

67

95

100

95

95

93

90

90

90

68

93

98

85

75

75

70

75

20th

69

75

93

75

70

0

0

0

0

70

95

95

90

85

25th

20th

20th

10th

71

80

93

55

80

25th

20th

10th

10th

72

45

93

50

30th

30th

35

35

20th

73

93

100

70

93

30th

55

45

25th

74

N.T. *

N.T. *

-

-

-

-

-

-

75

65

75

70

55

25th

30th

30th

20th

76

90

85

85

80

25th

20th

20th

0

77

85

100

90

75

25th

20th

20th

20th

78

90

98

95

75

20th

20th

20th

0

79

90

60

80

93

60

70

70

25th

80

0

20th

0

20th

0

0

0

81

70

98

85

80

35

65

65

25th

82

20th

25th

35

30th

0

0

0

0

83

75

100

75

85

35

20th

55

0

84

60

30th

45

40

63

55

40

30th

85

75

40

45

90

45

45

35

0

86

40

65

35

30th

0

0

0

0

87

90

90

90

90

65

70

70

25th

88

80

65

55

85

20th

20th

10th

10th

89

85

98

90

88

0

65

90

0

90

85

70

50

83

55

65

70

30th

91

83

98

85

75

25th

60

78

10th

92

0

0

0

0

0

0

0

0

93

70

80

65

80

30th

35

25th

0

94

25th

20th

20th

20th

0

0

0

0

95

65

65

65

40

25th

20th

0

0

96

65

70

70

55

0

0

0

0

97

70

80

65

55

0

0

0

0

a = tested at 15.6 micrograms / cm2 N.T. * = not tested

Table II A

Comparative compounds

Post-emergence herbicidal activity Application rate: 27.5 micrograms / cm2, unless otherwise stated broad-leaved plant grasses

Connect

% Phytotoxicity

% Phytotoxicity

dung

Chenopodi-

mustard

Amaranthus

soy

Digitaria

Paspalium

Savage

rice

No.

for album

retroflexus beans sanguinalis dilatatum

oats

C- 1

20th

20th

0

25th

0

0

0

0

C- 2

0

0

0

0

0

0

0

0

C- 3

0

0

0

0

0

0

0

0

C- 4

0

0

0

0

0

0

0

0

C- 5

0

0

0

0

0

0

0

0

C- 6

0

0

0

0

0

0

0

0

C- 7

0

0

0

0

0

0

0

0

C- 8

25th

20th

25th

30th

0

0

0

0

25th

659 651

Table II A (continued) Comparative Compounds Herbicidal Post-Emergence Activity Amount: 27.5 micrograms / cm2 unless otherwise stated

broad-leaved plants

Grasses

Connect

% Phytotoxicity

% Phytotoxicity

dung

Chenopodi-

mustard

Amaranthus

soy

Digitaria

Paspalium

Savage

rice

No.

for album

retroflexus beans sanguinalis dilatatum

oats

C- 9

20th

20th

io

25th

_

0

0

~ 0

C-10

0

0

0

0

0

0

0

0

C-ll

20th

0

0

20th

0

0

0

0

C-12

0

0

0

0

0

0

0

0

C-13

0

0

0

0

0

0

0

0

C-14

0

0

0

0

0

0

0

0

C-15

25th

25th

0

30th

25th

10th

45

45

C-16

0

0

0

0

0

0

0

0

As can be seen from the preceding Table I, the compounds according to the invention generally have a broad spectrum of excellent phytotoxic pre-emergence activity, which relates in particular to the compounds of numbers 2.4, 7.9, 12, 14, 16 and 22 . In addition, the compounds according to the invention are shown in Table II

20 a phytotoxic post-emergence activity against broad-leaved plants and in some cases against grasses in particular the compounds of numbers 7.9, 12.14, 16.22 and 23. It can also be seen that the corresponding comparison compounds have a poorer activity than the corresponding 25 possess compounds according to the invention.

M

Claims (15)

659 651 PATENT CLAIMS 1. Compound of the formula (I) wherein R lower alkyl with 1-4 carbon atoms, cycloalkyl with 2. Compound according to claim 1, characterized in that one of the radicals R1 or R2 is hydrogen, methyl, ethyl or propyl. 3rd 3-7 carbon atoms, lower alkenyl, haloalkyl with 1 ^ 4 carbon atoms and 1-3 halogen atoms, which are independently fluorine, chlorine, bromine and iodine, haloalkenyl with 2-4 carbon atoms and 1-3 halogen atoms, independently of one another fluorine, chlorine, bromine and iodine, lower alkoxy, lower alkylthio, lower alkoxyalkyl, in which the alkyl and alkoxy portions independently of one another have 1-3 carbon atoms, lower alkylthioalkyl, in which the alkyl portions independently contain 1-3 carbon atoms, phenyl, naphth-l-yl, indene-1- yl, 4-fluorophenyl, arylalkylene with 1-3 carbon atoms in the alkylene portion, where the aryl portion is phenyl, naphth-l-yl or indene-l-yl, means or R is substituted aryl or a substituted arylalkylene radical of the following group: _ R4 R3 3. A compound according to claim 1, characterized in that one of the radicals R1 or R2 is methyl or ethyl and the other is hydrogen, methyl or ethyl. 3-7 carbon atoms, lower alkenyl, haloalkyl with 1-4 carbon atoms and 1-3 halogen atoms, independently of one another fluorine, bromine or iodine, haloalkyl with 2-4 carbon atoms and 1-3 halogen atoms, independently of one another fluorine, chlorine, bromine and iodine, lower alkoxy , Lower alkylthio, lower alkoxyalkyl, in which the alkyl part and the alkoxy part independently have 1-3 carbon atoms, alkylthioalkyl, in which the alkyl parts independently have 1-3 carbon atoms, phenyl, naphth-l-yl, inden-l-yl, 4th 4th 4. A compound according to claim 1, characterized in that one of the radicals R1 or R2 is hydrogen and the other is methyl, ethyl or propyl. 4-fluorophenyl, arylalkylene having 1-3 carbon atoms in the alkylene radical and in which the aryl radical is phenyl, naphth-l-yl or inden-l-yl, or R represents substituted aryl or substituted arylalkylene, these substituents having the following formulas: 25th (R3 I. (R3 or wherein one, two or three of the radicals R4, R5, R6, R7, R8 and R9 are, independently of one another, lower alkyl, lower alkoxy, halogen, nitro and haloalkyl having 1-3 carbon atoms and 1-3 different or identical halogen atoms and the rest Residues are hydrogen and R3 represents a simple bond or an alkylene radical with 1-3 carbon atoms: R1 is hydrogen or alkyl having 1-4 carbon atoms, alkenyl having 3 or 4 carbon atoms, lower alkoxycarbonylalkyl, 5 lower alkoxyalkyl or lower alkylthioalkyl; or R1 and R2 together with the nitrogen atom to which they are attached represent a saturated or unsaturated nitrogen heterocycle with 3-6 ring atoms, in which ring one atom is nitrogen and the remaining atoms are carbon atoms; X is hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl and can be located at any position on the phenyl ring, and Y is lower alkyl, lower alkoxy, halogen, lower haloalkyl having 1-4 carbon atoms and 1-3 identical 15 or different halogen atoms, lower haloalkoxy having 1-4 Carbon atoms and 1-3 identical or different halogen atoms or lower halogen alkylthio with 1-4 carbon atoms and 1-3 identical or different carbon atoms, with the proviso that when Y is halogen 20, then R, R1 and R2 are not all hydrogen and with the further proviso that if Y is other than trifluoromethyl and X is not hydrogen and R1 and R2 are each hydrogen then R is methyl, ethyl, propyl, 2-halophenyl, 2-lower alkylphenyl or 4-fluorophenyl, as well as compatible salts of the compounds of formula I. . 5 5 wherein one, two or three of the radicals R4, R5, R6, R7, R8 and R9 independently of one another are lower alkyl, lower alkoxy, halogen, nitro or haloalkyl having 1-3 carbon atoms and 1-3 identical or different halogen atoms and the remaining radicals are hydrogen and R3 represents a simple bond or an alkylene radical with 1-3 carbon atoms; R1 is hydrogen or alkyl of 1-4 carbon atoms; R2 is hydrogen, alkyl of 1-4 carbon atoms, alkenyl of 3 or 4 carbon atoms, lower alkoxycarbonylalkyl, lower alkoxyalkyl or lower alkylthioalkyl; 659 651 R1 and R2 together with the nitrogen atom to which they are attached form a saturated or unsaturated nitrogen-containing heterocyclic ring containing 3-6 ring atoms, one of which is a nitrogen atom and the remaining carbon atoms; X is hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl and can be located anywhere on the phenyl ring; as well as compatible salts of the compound mentioned above. 19. A compound according to claim 18, characterized in that R1 and R2 are independently hydrogen, methyl or ethyl. 20. A compound according to claim 19, characterized in that one of the radicals R1 or R2 is methyl or ethyl and the other is hydrogen, methyl or ethyl. 21. A compound according to claim 18, characterized in that one of the radicals R1 or R2 is methyl or ethyl and the other is hydrogen. 22. A compound according to claim 19, characterized in that X is hydrogen and R is phenyl, naphthyl, 4-fluorophenyl, 2-halophenyl or 2-lower alkylphenyl. 23. A compound according to claim 22, characterized in that one of the radicals R1 or R2 is hydrogen and the other is hydrogen, methyl or ethyl. 24. A compound according to claim 23, wherein R is phenyl, 2-fluorophenyl, 2-chlorophenyl or 2-methylphenyl. 25. A compound according to claim 23, characterized in that R is phenyl. 26. A compound according to claim 23, characterized in that R is phenyl and one of the radicals R1 or R2 is hydrogen and the other is methyl. 27. A compound according to claim 23, characterized in that R is phenyl and one of the radicals R1 or R2 is hydrogen and the other is ethyl. 28. A compound according to claim 18, characterized in that R is lower alkyl, cycloalkyl, lower alkenyl, lower halo-genalkyl or lower haloalkenyl. 29. A compound according to claim 28, characterized in that R1 and R2 independently of one another are hydrogen, methyl or ethyl. 30. A compound according to claim 29, characterized in that R is methyl, ethyl or propyl. 31. A compound according to claim 30, characterized in that one of the radicals R1 or R2 is hydrogen and the other is methyl or ethyl and X is hydrogen. 32. Compound according to claim 29, characterized in that X is hydrogen. 33. Compound according to claim 18, characterized in that X is hydrogen. 34. Compound according to claim 1, characterized in that X is hydrogen. 35. Compound according to claim 34, characterized in that X denotes lower haloalkyl having 1-2 carbon atoms. 36. Herbicidal composition, characterized in that it contains a herbicidally effective amount of a compound according to claim 1 or mixtures or salts of such compounds and a compatible carrier. 37. Herbicidal composition according to claim 36, characterized in that it contains a herbicidally effective amount of a compound according to claim 25 or mixtures or salts thereof and a compatible carrier material. 38. A method for preventing the growth or destruction of plants, characterized in that a herbicidally effective amount of a compound according to claim 1 or mixtures or salts thereof is applied to the foliage or to the potential growth medium of these plants. 5 5. A compound according to claim 1, characterized in that X is hydrogen. 6. A compound according to claim 2, characterized in that X is hydrogen. 7. A compound according to claim 3, characterized in that X is hydrogen. 8. A compound according to claim 1, characterized in that R is phenyl, naphth-l-yl, 4-fluorophenyl or substituted aryl. 9. A compound according to claim 8, characterized in that R is phenyl, naphthyl or a monosubstituted phenyl radical. 10th 10th 15 20th 25th 30th 35 40 45 50 55 60 65 659 651 39. A method for preventing the growth or destruction of plants according to claim 38, characterized in that a herbicidally effective amount of a compound according to claim 25 or mixtures or salts thereof is applied to the foliage or to the potential growth medium of these plants. 40. Agent for regulating plant growth, characterized in that it contains an amount of a compound according to claim 1 or mixtures or salts thereof which is effective to change the growth of the plants. 41. A method for regulating the growth of plants, characterized in that an amount of a compound according to claim 1 or mixtures or salts thereof is applied to the foliage of the plants or to their growth medium, this amount being effective to influence the growth of the plants . 42. A process for the preparation of a compound as claimed in claim 1, in which RPhenyl, naphth-l-yl, indene-l-yl or substituted aryl is as defined in claim 1, characterized in that a corresponding compound of the formula v 10. A compound according to claim 9, characterized in that R is phenyl, halophenyl or lower alkylphenyl. 11. A compound according to claim 10, characterized in that R is phenyl, 4-fluorophenyl, 2-halophenyl or 2- Is lower alkylphenyl. 12. A compound according to claim 11, characterized in that X is hydrogen and R1 and R2 are independently hydrogen, methyl or ethyl. 13. A compound according to claim 1, characterized in that R denotes lower alkyl, cycloalkyl, lower alkenyl, haloalkyl or haloalkenyl. 14. A compound according to claim 13, characterized in that one of the radicals R1 or R2 is hydrogen, methyl or ethyl and the other is methyl or ethyl. 15. A compound according to claim 14, characterized in that R is methyl, ethyl or propyl. 16. A compound according to claim 15, characterized in that one of the radicals R1 or R2 is hydrogen and the 65 other means methyl or ethyl. 17. A compound according to claim 16, characterized in that X is hydrogen. 18. A compound according to claim 1, of the formula 35 45 55 60 (IA) wherein R lower alkyl with 1-4 carbon atoms, cycloalkyl with 15 are effective. Helvetica Chemica Acta, Volume 66, pages 362-378 (1983) discloses 5-N-cyclopropyl-4-phenyl-2-methoxycarbonyl-methylene-3-furanone as part of an academic chemical synthesis discussion. The U.S. Patent No. 4,441,910 relates to herbicidally active ureidosulfonyl furans and to ureidosulfonylthiophenes.