JPH06507606A - Substituted triazolinone - Google Patents

Abstract

(57) [Abstract] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

[Detailed description of the invention] Substituted triazolinone The present invention provides novel substituted triazolinones, multiple methods for their production, and herbicidal Regarding use as an agent.

Certain substituted triazolinones, such as 2-phenylaminocarbonyl-5- Morpholino-1,2-dihydro-3H-1,2,4-)riazol-3-one has been (see German Patent Application No. 2.042.660) . However, the properties of these known compounds, such as their herbicidal activity, are weak; If so, it does not meet the requirements for practical use in agriculture.

General formula (1) In the formula, R1 and R2 are each independently alkyl, alkenyl, alkyl, Quinyl, halogenoalkyl, halogenoalkenyl, halogenoalkynyl, cyano Alkyl, alkoxyalkyl, alkoxy, cycloalkyl, cycloalkyl alkyl, optionally substituted aryl, aralkyl or heteroaryl, or together with the nitrogen atom to which these are attached, optionally represents an optionally substituted heterocycle, R3 represents alkyl or cycloalkyl, R4 represents alkyl, alkenyl, Alkynyl, halogenoalkyl, 10genoalkenyl, halogenoalkynyl, Cyanoalkyl, hydroxyalkyl, alkoxyalkyl, aryloxia alkyl, arylthioalkyl, arylsulfinylalkyl, arylsul Honylalkyl, arylaminoalkyl, N-alkyl-arylaminoalkyl Kyl, arylazoalkyl, alkoxycarbonylalkyl, alkoxycal Bonylalkenyl, alkylaminoalkyl, dialkylaminoalkyl, each optionally substituted cycloalkyl, cycloalkylalkyl, represents cycloalkenyl or cycloalkenylalkyl or optionally substituted optionally substituted aralkyl, in each case optionally substituted aralkyl; aryl, arylalkenyl, arylalkynyl, aroyl, aryl, aralkyl or aryloxy, or alkoxy, alkenyloxy, represents cy or alkynyloxy, and X represents oxygen or sulfur, A novel substituted triazolinone has now been found.

Where appropriate, the compounds of formula (1) may be and exist in the form of geometric and/or optical isomers or isomer mixtures of various compositions. It is possible. The present invention relates to pure isomers and isomer mixtures.

Furthermore, a) General formula (II) triazolinone and/or in which R1, R1 and R3 have the above meanings; are the tautomers of these compounds, i.e. the corresponding hydroxytriazoles, if appropriate. For example, in the presence of reaction auxiliaries and, if appropriate, in the presence of diluents, the general formula (III) R4- N=C=X (III) Reacted with iso(thio)cyanate in which R4 and X have the above meanings. or b) General formula (IV) chlorocarbonyl-tria in which RI, R2 and R3 have the above meanings The zolinone, if appropriate, in the presence of an acid binder and, if appropriate, a diluent, is converted to the general formula (■) H, N-R' (V) In the formula, R4 has the above meaning, When reacting with the amine of formula (1), a novel triazolinone substituted product of general formula (1) is obtained. It was found that

Finally, novel substituted triazolinones of general formula CI) exhibit interesting herbicidal properties. It was found that

Surprisingly, the novel substituted triazolinones of general formula (I) are and a compound 2-phenylaminocarbonyl-5-morpho having a similar structure. Weeds from lino-1,2-dihydro-3H-1,2,4-triazol-3-one It was much more active against the larvae, but at the same time was well tolerated by important crops.

In the general formula, halogen is fluorine, chlorine, bromine and iodine, preferably fluorine , chlorine or bromine, especially fluorine or chlorine.

an optionally substituted aryl group, such as aryl, aralkyl or aryl one or more, preferably 1 to 5, especially 1 to 3, particularly preferred Preferably, it may have one or two identical or different substituents.

In aryl-containing groups, aryl preferably represents phenyl or naphthyl. vinegar.

The groups R1 and R2 together with the nitrogen atom to which they are attached form a heterocycle , these preferably contain 1.2 or an optionally trisubstituted heterocycle, in which case the substituent is the following: Things are chosen. i.e. halogen and 1 to 4 carbon atoms each and if appropriate 1 to 9 identical or different halogen atoms, preferably 1 to 5, especially 1 to 5 straight-chain or branched alkyl in each case having 3 or /% logeno It is an alkyl. Methyl, ethyl, n- or i-propyl, chlorine and trif Fluoromethyl is a particularly preferably chosen substituent.

The heterocyclic group in the meaning of heterocyclic alkyl for R4 is preferably the following heterocyclic group: represents ・ In the formula, Z represents oxygen or sulfur in each case.

Alkyl in the sense of heterocyclic alkyl is, for example, methyl, ethyl, n- or represents iso-propyl, n-, iso-1sec- or t-butyl.

Heterocycle in the sense of heterocyclic alkyl has 1 to 4 carbon atoms, preferably 1 or is 2 and 1 to 9, preferably 1 to 5, same or different halogen atoms, In particular straight-chain or branched alkyl or halo having from 1 to 3 in each case genoalkyl, or in each case divalent alkanedi having up to 4 carbon atoms; one or more identical or different substituents from the group consisting of yl or alkenediyl; or polysubstituted, preferably 1 to 3 substitutions, especially 1 or 2 substitutions. As a substituent The groups chosen are in particular methyl and ethyl.

Preferred compounds of formula (1) are also those in which R1 and R1 are, independently of each other, in each case linear. branched alkyl having 1 to 8 carbon atoms, having 2 to 8 carbon atoms; alkenyl having 2 to 8 carbon atoms, alkynyl having 1 to 8 carbon atoms and halogenoalkyl having 1 to 17 identical or different halogen atoms, each 2 to 8 carbon atoms and 1 to 15 same or different halogen atoms or 1 to 8 carbon atoms halogenoalkenyl or halogenoalkynyl having 13, each individual alkynyl Cyanoalkyl, alkoxyalkyl or alkoxyalkyl having 1 to 6 carbon atoms in the kill moiety is alkoxy, cycloalkyl having 3 to 7 carbon atoms, cycloalkyl moiety cycloalkyl having 3 to 7 carbon atoms in the alkyl part and 1 to 6 carbon atoms in the alkyl part represents alkyl, or has 6 to 10 carbon atoms in the aryl part and alkyl Aralkyls having 1 to 6 carbon atoms in the moiety, ants having 6 to 10 carbon atoms carbon atoms or 2 to 9 carbon atoms and heteroatoms, especially nitrogen, oxygen and/or sulfur. represents a heteroaryl having 1 to 3, each of these substituents optionally It may be mono- or polysubstituted with the same or different substituents (herein, each Suitable substituents include halogen, cyano, nitro, and each having 1 to 4 carbon atoms. and in each case with 1 to 9 identical or different halogen atoms, as appropriate. Straight-chain or branched alkyl, alkoxy, alkylthio, halogenoa alkyl, halogenoalkoxy or halogenoalkylthio, or Further, if R1 and R2 are suitable together with the nitrogen atom to which they are bonded, may contain 1 to 2 heteroatoms, in particular nitrogen, oxygen and/or sulfur, and It may optionally be mono- or di-substituted with the same or different substituents, in which case Suitable substituents include halogen and each having 1 to 4 carbon atoms, if appropriate, identical or has 1 to 9 different halogen atoms and also 1 to 2 oxo or thiono groups. in each case where the straight-chain or branched alkyl or halogenoalkyl represents a certain 5- to lo-membered heterocycle, R3 is straight-chain or branched alkyl or carbon having 1 to 8 carbon atoms; represents cycloalkyl having 3 to 8 atoms, if R4 is in each case linear or branched alkyl having 1 to 18 carbon atoms, or branched alkyl having 2 to 8 carbon atoms; alkenyl having 2 to 8 carbon atoms, alkynyl having 1 to 8 carbon atoms and halogenoalkyl having 1 to 17 identical or different halogen atoms, each 2 to 8 carbon atoms and 1 to 15 same or different halogen atoms or 1 to 8 carbon atoms halogenoalkenyl or halogenoalkynyl having 13 carbon atoms 1 to 8 cyanoalkyl having 1 to 8 carbon atoms and 1 to 6 hydroxyl groups represents hydroxyalkyl having 1 to 4 carbon atoms in each alkyl moiety phenoxyalkyl, phenylthioalkyl, phenylsulfinylalkyl , phenylsulfonylalkyl, phenylaminoalkyl, N-(C, ~C4 -alkyl)-phenylaminoalkyl or phenylazoalkyl , alkoxyalkyl, alkoxyalkyl, having up to 6 carbon atoms in each individual alkyl represents koxycarbonylalkyl or alkoxycarbonylalkenyl, alkylaminoalkyl having 1 to 6 carbon atoms in each individual alkyl moiety or dialkylaminoalkyl, respectively cycloalkyl or cyclo 3 to 8 carbon atoms in the alkenyl moiety and 1 to 8 carbon atoms in the alkyl moiety, if appropriate. 6, and may optionally be substituted with 1 to 3 substituents, the same or different. Suitable substituents include in each case halogen, cyano, phenyl and 1 to 4 carbon atoms and, if appropriate, 1 to 9 identical or different halogen atoms straight-chain or branched alkyl or halogenoalkyl in each case with and 1 to 4 carbon atoms and 1 to 5 same or different halogen atoms. straight-chain or branched halogenoalkenyl having 4 carbon atoms each A system in which there is a divalent alkanediyl or alkenediyl in each case with up to Chloalkyl, cycloalkylalkyl, cycloalkenyl or cycloalke represents nylalkyl, or R4 is further a linear or branched alkyl moiety. 1 to 6 carbon atoms and 2 to 9 carbon atoms and heteroatoms in the heterocyclic moiety, especially containing 1 to 3 nitrogen, oxygen and/or sulfur, and from time to time in the same or different locations. It may be mono- or polysubstituted with substituents (in this case, suitable substituents include halogen, cyano, nitro and each with 1 to 5 carbon atoms and, if appropriate, the same or different in each case straight-chain or branched alkyl having 1 to 9 halogen atoms; alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halo represents a heterocyclic alkyl with genoalkylthio or alkoxycarbonyl or R4 is further in each case linear or branched and has from 1 to 8 carbon atoms. alkoxy, alkenyloxy having 2 to 8 carbon atoms or 2 carbon atoms alkynyloxy having ~8 or 6 to 10 carbon atoms in each aryl moiety 1 to 8 carbon atoms in the straight-chain or branched alkyl moiety, if appropriate. carbon atom in a straight-chain or branched alkenyl or alkynyl moiety In this case, the hydrogen atom of the α carbon atom is replaced by ethane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl or propane-1,5-diyl yl, each optionally substituted with 1 to 3 substituents, which may be the same or different. where appropriate alkyl substituents include halogen and silicon, as appropriate. ano, and suitable aryl substituents include in each case halogen, cyano, Nitro, amino, hydroxyl, each with 1 to 6 carbon atoms in the alkyl moiety and as appropriate Then, in each case linear chain having 1 to 9 identical or different halogen atoms or branched alkyl, alkoxy, alkylthio, halogenoalkyl, Halogenoalkoxy, halogenoalkylthio, alkylsulfinyl, alkyl Sulfonyl, halogenoalkylsulfinyl, halogenoalkylsulfonyl, Lucanoyl or alkoxycarbonyl, cycloalkyl having 3 to 6 carbon atoms alkanediyl, oxaalkanediyl and phenoxy having up to 5 carbon atoms. ralkyl, arylalkenyl, arylalkynyl, aroyl, aryl, aryl represents ralkyloxy or aryloxy: or R4 is a phenyl moiety represents benzyl with a fused 10-CH, -0- group, and X represents oxygen or sulfur.

Particularly preferred compounds of formula (I) are those in which R1 and R2 are, independently of each other, in each case thyl, ethyl, n- or i-propyl, n-1i-1S- or t-butyl allyl, n- or i-pentyl, allyl, propargyl, in each case also linear or branched, in each case containing 1 to 9 identical or different halogen atoms. halogenoalkyl having 1 to 4 carbon atoms, having 3 to 6 carbon atoms represents halogenoalkenyl or halogenoalkynyl having 3 to 6 carbon atoms. Wasuka, cyanoethyl, methoxymethyl, methoxyethyl, methoxy, ethoxy , cyclopropyl, cyclopropylmethyl, cyclopentyl, cyclohexyl, Represents cyclohexylmethyl, cyclohexylethyl, cyclopentylmethyl or each may optionally be substituted with 1 to 3 substituents, which may be the same or different. Particularly suitable substituents include fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-1i-1S- or t-butyl, methoxy, Ethoxy, methylthio, trifluoromethyl, trifluoromethoxy or tri Does fluoromethylthio represent benzyl, phenylethyl or phenyl? , or R1 and R2 together with the nitrogen atom to which they are attached each It may optionally be substituted with 1 to 3 substituents, which may be the same or different. Substituents include methyl, ethyl, n- or i-propyl, chlorine or trifluor. Formulas with oromethyl represents a heterocycle, Rj is methyl, ethyl, propyl, isoflovir, n-1i -1S- or t-butyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, R4-h<methyl, ethyl, n- or i- propyl, n-1i-1S- or t-butyl, in each case linear or Branched pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl or allyl, in each case straight-chain or branched butenyl, pen thenyl or hexenyl, propargyl, in each case linear or branched butynyl, pentynyl or hexynyl, with 1 to 8 carbon atoms and the same or Also linear with 1 to 9 different halogen atoms, especially fluorine, chlorine or bromine or branched halogenoalkyl, each having 3 to 8 carbon atoms and a halogen atom, In particular linear or branched chains containing 1 to 3 fluorine or chlorine halogenoalkenyl or halogenoalkynyl, 1 to 6 carbon atoms in the alkyl moiety straight-chain or branched cyanoalkyl in each case with 1 carbon atom hydroxyalkyl having ~6 and 1 to 3 hydroxyl groups, each individual Alkoxyalkyl having up to 4 carbon atoms in the alkyl or alkenyl moiety , alkodicarbonylalkyl or alkoxycarbonylalkenyl, alkodicarbonylalkyl or alkoxycarbonylalkenyl represents kylaminoalkyl or dialkylaminoalkyl, or each It may optionally be substituted with 1 to 3 substituents, which may be the same or different. substituents include in each case fluorine, chlorine, bromine, methyl, ethyl, n- or l-propyl, n-1i-1S- or t-butyl, cyano, methanediyl, cyclopropyl with ethanediyl, butanediyl or butadienediyl, Cyclopropylmethyl, cyclopropylethyl, cyclobeni/thyl, cyclohexyl sil, cycloheptyl, cyclooctyl, cyclopropylmethyl, cyclohexy ruethyl, cyclohexenyl or cyclohexenylmethyl or dichloroaryl and R4 is optionally the same or different substituent in the cyclic moiety; may be substituted 1 to 3 with , suitable heterocycles have groups in each case, where in which Z represents oxygen or sulfur in each case and the appropriate substituents are fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or ]- Propyl, n-1i-1S- or t-butyl, methoxy, ethoxy, methyl thio, trifluoromethyl, trifluoromethoxy or trifluoromethylthi R represents a heterocyclic methyl, a heterocyclic propyl or a heterocyclic ethyl; 4 is furthermore in each case a straight-chain or branched atom having 1 to 6 carbon atoms; lukoxy, alkenyloxy having 3 to 6 carbon atoms or 3 to 6 carbon atoms represents alkynyloxy having the same or different positions, or It may be substituted with 1 to 3 substituents, in which case each suitable phenyl substituent is Fluorine, chlorine, bromine, hydroxyl, cyano, nitro, methyl, ethyl, n- or i-propyl, n-1i-1S- or t-butyl, methoxy, Ethoxy, methylthio, difluoromethyl, trifluoromethyl, difluoromethane Toxy, trifluoromethoxy, trifluoromethylthio, trifluoromethyl Sulfinyl, trifluoromethylsulfonyl, methylsulfinyl, methyls sulfonyl, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl , n- or i-propoxycarbonyl, cyclohexyl or phenoxy benzyl, phenylethyl, fluorine, which may optionally be linear or branched; phenylpropyl, phenylpropenyl, phenylpropynyl, phenylbutyl, Phenylbutenyl, phenylbutynyl, phenylpentyl, phenylpentenyl , phenylpentynyl, phenylhexyl, phenylhexenyl, phenylhexyl Cynyl, phenylheptyl, phenylheptenyl, phenylheptenyl, phenyl luoctyl, phenyl octenyl, phenyl octenyl, phenylcyanomethyl , phenylcyanoethyl, phenylcyanopropyl, benzyloxy, phenyl Ethyloxy, phenoxy, phenoxyethyl, phenoxyprobil, phenoxy C-1-propyl1. Phenoxyisobutyl, phenoxyt-butyl, phenyl ruthioisobutyl, phenylthio-t-butyl, phenylthioethyl, phenyl represents thiopropyl, phenylthio-1-propyl, benzoyl or naphthyl and X represents oxygen or sulfur.

Very particularly preferred compounds of formula (1) are those in which R1 is methyl, ethyl, n- or i- propyl, n-11-1S- or t-butyl, n- or i-pentyl, represents cyclopropyl, cyclopentyl or cyclohexyl, R2 is methyl, ethyl, n- or i-propyl, n-11-1S- or represents t-butyl, n- or 1-pentyl, or R1 and R2 are also together with the nitrogen atom to which it is attached represents a heterocycle of the formula, R3 represents methyl, ethyl, propyl or isopropyl, especially methyl; 4 may optionally be substituted with 1 to 3 of the same or different substituents, and Particularly suitable phenyl substituents include in each case fluorine, chlorine, bromine, methyl, ethyl n- or i-propyl, n-1i-1S- or t-butyl, trifyl fluoromethyl, phenyl, methoxy, ethoxy, propoxy, isopropoxy, Difluoromethoxy, trifluoromethylcy, difluoromethyl, methoxyl Bonyl, ethoxycarbonyl, propoxycarbonyl, cyano, methylthio, ethyl Chilthio, propylthio, isopropylthio, difluoromethylthio, triflu Oromethylthio, methylsulfinyl, methylsulfonyl and trifluoromethyl 1-methyl-3-phenyl-propyl, 1-ethyl-3-phenyl with sulfonyl phenyl-propyl, 1-propyl-3-phenyl-propyl, 1-isopropyl -3-phenyl-propyl, 2-methyl-3-phenyl-propyl, 1゜1-di Methyl-3-phenyl-propyl, 1-methyl-1-ethyl-3-phenyl-propyl Lopyl, 1,1-diethyl-3-phenyl-propyl, 1-methyl-1-propyl -3-phenyl-propyl, 1-methyl-3-phenyl-2-propenyl, 1 -ethyl-3-phenyl-2-propenyl, 1-propyl-3-phenyl-2- Propenyl, 1-isopropyl-3-phenyl-2-propenyl, 1,1-dime thyl-3-phenyl-2-propenyl, 1-methyl-1-ethyl-3-phenyl -2-propenyl, 1,1-diethyl-3-phenyl-2-propenyl, 1-methyl Tyl-1-propyl-3-phenyl-2-propenyl, 1-methyl-3-phe= -2-propynyl, 1-ethyl-3-phenyl-2-'rovinyl, 1-propynyl -3-phenyl-2-propynyl, 1-isopropyl-3-phenyl-2-propynyl Ropynyl, 1,1-dimethyl-3-phenyl-2-propynyl, 1-methyl-1 -ethyl-3-phenylene/l/-2-furobinyl, 1,1-diethyl-3-phenylene -2-propynyl, 1-methyl-1-propyl-3-phenyl-2-propynyl 1,2-dimethyl-3-phenyl-propyl, 2-ethyl-1-methyl-3 -phenyl-propyl, 1.2.2-trimethyl-3-phenyl-propyl, 1 , 3゜3-trimethyl-3-phenyl-propyl or 1.1.2.2-tetra represents methyl-3-phenyl-propyl, and X represents oxygen. .

For example, 5-dimethylamino-1-methyl-1,2-dihydro- 3H-1,2,4-) riazol-3-one and 3-methyl-4-phenyl-2- When using butyl isocyanate, the reaction route of step (a) according to the invention is as follows: It can be expressed by the formula: For example, as the starting material 2-chlorocarbonyl-1-methyl-5-piperidi81 ．． 2-dihydro-3H-1,2,4-triazol-3-one and 1-(4-k) When using lorophenyl)-3-amitubukun, the reaction of step (b) according to the invention The reaction route can be represented by the following formula: In intermediates and precursors, also of formula (I) The groups defined in the active compounds (RISR", X, etc.) are used in compounds of formula (1) shall have the meaning given to all range definitions in this section. same thing as well also applies to groups mentioned several times in the precursors and intermediates.

Starting materials of formula (II) or the corresponding tautomeric hydroxytriazoles are disclosed and/or can be produced by methods known per se (German patent). Patent Application Publication No. 2.042.660, Publication No. 2,330.089, Publication No. 2.42 No. 8.204, see specification No. 2.537.973).

The triazolinone of formula (II) is, for example, of formula (VI), where R1 and R2 have the above meanings. cyanamide of formula (VII) CI-C at a temperature between 20 and 150°C. OOR(VII) where R represents methyl, ethyl or phenyl, preferably phenyl, The resulting formula (VIII) R1゜ Chloroformamidine derivatives in which R, R' and R2 have the above meanings O to 1 after isolation, if appropriate by distillation in vacuo or by other conventional methods. 00°C, if appropriate with diluents such as methylene chloride, dioxane and/or or diethyl ether in the presence of formula (IX) R”-NH-NH2(IX) In the formula, R3 has the above meaning, of alkylhydrazine and the product is treated in a conventional manner. (See manufacturing examples).

The starting materials of formula (III) are organic chemicals known for synthesis [eg N.

uv, J, Chim, 1 (1977), 243-254-Chea+, A bstructs87: cited in 151614a; Liebigs Ann, Chew, 562 (1949), 75-136; 5ynthesis 1990.803-815; see manufacturing examples].

The starting material of formula (IV) was not hitherto known from the literature, but a previous, non-preferential publication Non-prior-published Patent App (German Patent No. 3.939.952) /LeA 27, 343).

Chlorocarbonyl-triazolinone of formula (rv) is of formula (II) R1゜ In the formula, R1, R2 and R3 have the above meanings, and O to 1 triazolinone at a temperature of between 50°C and, if appropriate, in the presence of an acid binder such as tolumethylamine. React with phosgene in the presence of a diluent e.g. toluene or acetonitrile if appropriate. Obtained if

The starting materials of formula (v) are known and/or may be prepared by methods known per se. [J, Med, Chew, 25 (1982), 1362-1370] ;Tetrahedron Lett, 29 (1988), 223-22 4: Chem, Ber, 117 (1984), 856-858; Germany National Patent Application Publication No. 3,426,919; European Patent Application Publication No. 237゜3 No. 05; J, Am, Chem, Sac, 71 (1949), 34 82-3485 + Tetrahedron Lett, 27 (1986) , 3957-3960: Bull, Soc, Chim, France 19 74 (3-4, Pt, 2), 615-622; Tetrahedron Lett, 31 (1990), 2661-2664: J, Med, Ch. Em, 13 (1970), 1249-1250; see Manufacturing Examples].

Preparation step (a) of the novel substituted triazolinones of formula (I) according to the invention is preferably Preferably, a diluent is used. Diluents suitable for this purpose include virtually all inert It is an organic solvent.

These include preferably aliphatic and aromatic, optionally halogenated Good hydrocarbons such as pentane, hexane, heptane, cyclohexane, petroleum acetate Tel, benzine, ligroin, benzene, toluene, xylene, methylene chloride, Ethylene chloride, chloroform, carbon tetrachloride, chlorobenzene and 0-dichlorobenzene ethers such as diethyl ether, dibutyl ether, glycol dimethyl Thyl ether and diglycol dimethyl ether, tetrahydrofuran and dimethyl ether Oxane, ketones such as acetone, methyl ethyl ketone, methyl isopropyl ketone and methyl isobutyl ketone, esters such as methyl acetate and ethyl acetate, Nitriles such as acetonitrile and propionitrile, amides such as dimethyl fluoride lumamide, dimethylacetamide and N-methyl-pyrrolidone, and also dimethylacetamide and N-methyl-pyrrolidone. Methyl sulfoxide, tetramethylene sulfone and triamine hexamethyl phosphate Contains de.

If appropriate, step (a) according to the invention may be carried out in the presence of a basic reaction auxiliary.

Suitable basic reaction auxiliaries are all customary inorganic and organic bases. I prefer the following Suitably used: tertiary amines such as triethylamine, N,N-dimethylaniline , pyridine, N,N-dimethylaminopyridine, diazabicyclooctane (DA BCO), diazabicyclononene (DBN) or diazabicycloundecene (D B U).

However, the addition of such catalysts is not essential.

When carrying out step (a) according to the invention, the reaction temperature can be varied within a substantial range. one Generally, the kneading process is carried out at a temperature between 0°C and 150°C, preferably between 4°C and 120°C. Do it with

Step (a) according to the invention is usually carried out under atmospheric pressure. However, the true nature is also It can also be carried out under pressure if the starting compound is a gas.

For carrying out step (a) according to the invention, per mole of triazolinone of formula (II) 1 to 5 mol, preferably 1 to 2.5 mol of iso(thio)cyanate and if appropriate Generally, 1 to 2.5 moles of reaction aid are used. Carry out the reaction and collect the reaction product in general (see Preparation Examples).

Suitable diluents for carrying out step (b) are also inert organic solvents. Suitably used The solvents used are those listed in step (a).

If appropriate, step (b) according to the invention is carried out in the presence of a suitable acid binder. Appropriate Acid binders are all customary inorganic or organic bases. These include, for example, alkali metal hydroxides such as sodium or potassium hydroxide, alkali gold genus carbonates such as sodium carbonate, potassium carbonate or sodium bicarbonate, and Also, tertiary amines such as triethylamine, N,N-trimethylaniline, pyridine N,N,N-dimethylaminopyridine, diazabicyclooctane (DABCO) , diazabicyclononene (DBN) or diazabicycloundecene (D U) is included.

The amine of formula (V) used as a reactant can also simultaneously act as an acid binder. A suitable excess may be used to

When carrying out step (b) according to the invention, the reaction temperature can be varied within a substantial range. . Generally, the nature is at a temperature between 0 and 150°C, preferably between 10 and 80°C. Do it with

Process ffl (b) according to the invention is usually carried out under atmospheric pressure. However, also pressurized You can also do it below.

To carry out step (b) according to the invention, chlorocarbonyltriazo of formula (IV) 1 to 5 mol, preferably 1 to 2.5 mol of amine of formula (V) per mol of linone and and if appropriate 1 to 2.5 moles of acid binder are generally used. Perform the reaction and generally The reaction product is worked up and isolated analogously to known methods (see Preparation Examples).

The active compounds according to the invention are useful as defoliants, desiccants, hardwood destroyers and, in particular, as pesticides. Can be used as a herbicide. Weeds, in the broadest sense, are plants that It means any plant that grows in a place where it is not. The substance according to the invention essentially Depending on the amount used, it acts as a complete herbicide or a selective herbicide.

The compounds according to the invention can be used, for example, in connection with the following plants:

Dicotyledonous weeds of the following genera: Mustard (S. napis), S. napis (S. Letpidium), Galium, Chickweed (Stel laria), Matricaria, An theIIlis), Galinsoga, Chenopodium (Che nopodium), Urtica, Senecio ), Amaranthus, Purslane (p□rjulaca) , Xanthiu+++, Convolvulus ), sweet potato (I pomoea), polygonum (P oligonum), S esbania, Ambrosia, thistle Genus (Cirsium), Genus (Brduus), Genus (S) nchus), Solanum, Rolippa , Rotala, L1ndernia, Lamilla Lamium, Veronica, A butilon), Emex (Emex), Datura (Dat) ura), Viola, Galeopsis , Papaver and C61taurea.

Dicotyledonous cultivated plants of the following genera: Cotton genus (G ossypiuo+), Soybean genus (Gl ycine), Chard genus (Beta), Carrot genus (Daucus), Phaseolus, Pisum, Solanum (S olanum), Linum (Linum), Sweet potato (I pomo) ea), Vicia, Nicotiana, Tomato Lycopersicon, Arachis, Abu B rassica, L actuca, cucumber Cucumis and Cucurbita.

Monocotyledonous weeds of the following genera: Echinochloa, Echinochloa, S. etaria), millet genus (P aniculI), mehimba genus (D 1g1t aria), P. hleum, Poa. , Festuca, E1eusine, B rachiaria, Lolium, Su B romus, Avena, Cyperus Cyperus, Sorghum, Cyperus A gropyron, Cynodon, Mo. nocharia), Fimbristylis, Omodaka ( S agittaria), E 1eocharis, Firefly genus (S circus), Bassbalum (P aspalum), Platypus ( I schaemum), Sphenoclea, Dac D actyloctenium, Agros tis), A. Lopecurus and Apella (A. era).

Monocotyledonous cultivated plants of the following genera: Oryza (Oryza), Maize (Zea), Triticum (Triticum), Barley (Hordeul I+), Carasum Avena, rye (S ecale), sorghum (S org) hum), Panicum, Saccharum ), Ananas, Asparagus and and Allium.

However, the use of the active compounds according to the invention is not entirely limited to these genera. It also extends to other plants in the same way.

Depending on the concentration, the compound may be found in areas such as industrial areas and on railway tracks, where trees are present, etc. Or it is suitable for complete control of weeds on roads and open spaces where they do not exist. Equivalently, the compound are perennial cultivated plants, such as silviculture, ornamental trees, orchards, vineyards, and citrus trees. walnut orchards, banana plantations, coffee plantations, tea plantations, rubber tree plantations. Forests, oil palm plantations, cacao plantations, small fruit tree plantings and hop cultivation plants. It can be used for the selective control of weeds in soil-grown plants and for the selective control of weeds in soil-grown plants. can.

The compounds of formula (I) according to the invention can be used in the cultivation of monocots and dicots by pre- and post-emergence injection. It is particularly suitable for selectively controlling monocotyledonous and dicotyledonous weeds in plants.

To some extent they are also used as defoliants or foliar insecticides in cotton. Can be used.

The permeation of compounds of formula (1) in soil is extremely slow; therefore, groundwater contamination is substantially Can be excluded.

The active compounds can be present in common compositions, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, etc. , liniments, soluble powders, granules, suspensions - emulsion thickeners, natural products impregnated with active compounds and synthetic materials, as well as into microscopic capsules in polymeric materials.

These compositions can be prepared in a known manner, for example by combining the active compound with an extender, i.e. a liquid solution. medium and/or solid carrier and optionally surfactants, i.e. emulsifiers and/or dispersants and and/or a blowing agent.

Also, when using water as an extender, for example, an organic solvent may be used as an auxiliary solvent. You can also do it. As a liquid solvent, mainly aromatic hydrocarbons such as xylene and toluene are also used. or alkylnaphthalene, chlorinated aromatic or chlorinated aliphatic carbon Hydrogenides such as chlorobenzene, chloroethylene or methylene chloride, aliphatic carbons Hydrogenides such as cyclohexane, or paraffins such as mineral oil fractions, mineral oils and vegetable oils oils, alcohols such as butanol or glycols and their ethers and ster, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strong polar solvents such as dimethylformamide and Methyl sulfoxide as well as water are suitable.

As solid carriers, e.g. ammonium salts and ground natural minerals, e.g. clay, talc, chalk, quartz, attapulgite, montmorillonite , or diatomaceous earth as well as ground synthetic minerals such as highly dispersed silicic acid, aluminum silicates are suitable; as solid carriers for granules, they can be ground and separated. Separated natural rocks such as calcite, marble, pumice, sepiolite and dolomite as well as inorganic and Organic ground synthetic granules and granules of organic substances such as sawdust, palm, corn Rokosi cobs and tobacco stalks are suitable: non-ionic as emulsifier and/or foaming agent. anionic and anionic emulsifiers such as polyoxyethylene-fatty acid esters, polyol xyethylene aliphatic alcohol ethers such as alkylaryl polyglycols Ether, alkyl sulfonate, alkyl sulfate, aryl sulfone as well as albumin hydrolysis products; as dispersants, e.g. Sulfite waste liquor and methylcellulose are suitable.

Adhesives such as carboxymethylcellulose and powdered, granular or latex Natural and synthetic polymers such as gum arabic, polyvinyl alcohol and polyvinyl alcohol acetate and natural phospholipids such as cephalin and lecithin, and synthetic phospholipids such as cephalin and lecithin. Lipids can be used in the composition. Additionally, additives may be mineral and vegetable oils. can.

Colorants such as inorganic pigments such as iron oxide, titanium oxide and Prussian blue; Organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and Amounts of nutrients such as iron, manganese, boron, copper, cobalt, molybdenum and zinc Salt can be used.

The preparations generally contain between 0.1 and 95% by weight of active compound, preferably between 5 and 90% by weight. Contains between % and %.

The active compounds according to the invention are also publicly available, either as such or in the form of their preparations. It can also be used to control weeds as a mixture with known herbicides and finished Blends or seed mixtures are possible.

Herbicides suitable for the mixture are known herbicides, such as those for controlling weeds in cereals. -Amino-6-ethylthio 3-(2,2-dimethylpropyl)-1゜3.5- Triazine-2,4-(LH,3H)-dione (AMETHYDI0NE) or N-(2-benzothiazolyl)-N,N'-dimethylurea (METAB ENZTHIAZURON); 4-amino- for controlling weeds in sugar beets 3-Methyl-6-phenyl-1,2,4-triazin-5(4H)-one (ME TAMITRON) and 4-amino-6-(1, 1-dimethylethyl)-3-methylthio-1,2,4-triazine-5(4H) -one (METRIBUZIN); Furthermore, 2,4-dichlorophenoxyacetic acid ( 2,4-D): 4-(2,4-dichlorophenoxy)-butyric acid (2,4-DB ); 2,4-dichlorophenoxypropionic acid (2,4-DP): 5-(2 -Chloro-4-trifluoromethyl-phenoxy)-2-ditorobenzoic acid (AC IFLUORFEN); 2,6-diethyl-N-methoxy-methylchloroacetate Anilide (ALACHLOR); Methyl-6,6-dimethyl-2,4-dioxo -3-[1-(2-propenyloxyamino)-butylidenecocyclohexane Carboxylic acid (ALLOXYDIM): 4-amino-benzenesulfonylcarba Methyl mate (ASULAM); 2-chloro-4-ethylamino-6-ib Robylamino-1,3,5-1-riazine (ATRAZINE): 2- [[ [[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]- methyl]-amino]-sulfonyl]-methyl]-benzoate (BENSULFURON) ); 3-isopropyl-2,1,3-benzothiadiazin-4-one 2,2- Dioxide (BENTAZONE); 5-(2,4-dichlorophenoxy)-2 -Methyl nitrobenzoate (BI FENOX); 3,5-dibromo-4-hydro Roxy-benzonitrile (BROMOXYNIL); N-(butoxymethyl)- 2-chloro-N-(2,6-dinitylphenyl)-acetamide (BUTACH LOR), 5-amino-4-chloro-2-phenyl-2,3-dihydro-3-o Xypyridazine (CHLORIAZON); 2-I [(4-chloro-6- Medoxy 2-pyrimidinyl)-aminocarbonyl]-aminocarbonyl]-a Ethyl minosulfonyl)-benzoate (CHLORIMURON); lorophenyl)-isopropyl carbamate (CHLORPROPHAM); 2-chloro-N-f [(4-methoxy-6-methyl-1,3,5-triazine -2-yl)-amino]-benzenesulfonamide (CHLOR 5ULFURON): N,N-dimethyl-N'-(3-chloro-4-methylphenylene) (CHLORTOLURON): Exo-1-methyl-4-(1 -methylethyl)-2-(2-methylphenyl-methquin)-7-oxapisoc Rho(2,2,1)-hebutane (CINMETHYL IN); 3,6-dimethyl Lolo-2-pyridinecarboxylic acid (CLOPYRALID); 2-chloro-4-ethyl Thylamino-6-(3-cyanopropylamino)-1,3,5-triazine (C YANAZINE); N,S-diethyl-N-cyclohexylthiocarbamate (CYCLOATE); 2-[1-(ethoxyimino)-butyl]-3-hy Droxy-5-[tetrahydro-(2H)-thiobilan-3-yl]-2-cyc Lohexen-1-one (CYCLOXDIM): 2-[4-(2,4-dichloro phenoxy)-phenoxy]-propionic acid, its methyl ester or its ester Tyl ester (DICLOFOP); 2-[(2-chlorophenyl)-methy ]-4,4-dimethylisoxazolin-3-one (DIMETHAZONE) ; S-ethyl N, N-di-n-propyl-thiocarbamizo-1-(EPTAME ): 4-amino-6-t-butyl-3-ethylthio-1,2゜4-triazine -5(4H)-one (ETHloZIN); 2-[4-[(6-chloro-2 -benzoxazolyl)-oxy]-phenoxy)-propionic acid, its methyl ether Stel or its ethyl ester (FENOXAPROP); 2-E4- (5-trifluoromethyl-2-pyridyloxy)-phenoxy]-propanoic acid or its butyl ester (FLUAZIFOP); N,N-dimethyl-N'- (3-1-lifluoromethylphenyl)-urea (FLUOMETURON); 1-Methyl-3-phenyl-5-(3-trifluoromethylphenyl)-4- Pyridone (FLURIDONE); [(4-amino-3゜5-dichloro-6- Fluoro-2-pyridinyl)-oxy]-acetic acid or its 1-methylbutyl ether STER (FLUROXYPYR); 5-(2-chloro-4-trifluoromethane) methyl-phenoxy)-N-methylsulfonyl-2-nitropenzamide (FOM ESAFEN);2-+4-[(3-chloro-5-(trifluoromethyl )-2-pyridinyl)-oxy]-phenoxy)-propanoic acid or its ethyl Ester (HALOXYFOP): 3-cyclohexyl-6-dimethylamino -1-methyl-1,3,5-triazine-2,4-dione (HEXAZ　I　0 NE); 2-[4,5-dihydro-4-methyl-4-(1-methylethyl)- Methyl 5-oxo-IH-imidazol-2-yl]-4(5)-methylbenzoate IMAZAMETHABENZ: 2-[5-methyl-5-(1-methybenz) (ethyl)-4-oxo-2-imidacylin-2-yl]-3-quinolinecarbo 2-[4,5-dihydro-4-methyl-4- Isopropyl-5-oxo-(IH)-imidazol-2-yl]-5-ethylpi Lysine-3-carboxylic acid (IMAZETHAPYR); 3.5-short-4- Hydroxybenzonitrile (IOXYNIL); N.

N-dimethyl-N'-(4-isopropylphenyl)-urea (I5OPRO TURON);2-(Ethoxy-1-methyl-2-oxo-ethyl)-5-[ 2-chloro-4-(trifluoromethyl)-phenoxy]-2-nitrobenzoe LACTOPEN; (2-methyl-4-chlorophenoxy)-acetic acid ( MCPA); (4-chloro-2-methylphenoxy)-propionic acid (MCP P): N-methyl-2-(1,3-benzothiazol-2-yloxy)-aceto Anilide (MEFENACET); 2-chloro-N-(2,6-dimethylphene Nyl)-N-[(IH)-pyrazol-1-ylmethyl]-acetamide (ME TAZACHLOR); 2-ethyl-6-methyl-N-(1-methyl-2-methyl toxyethyl)-chloroacetanilide (METOLACHLOR); 2-1 [[((4-methoxy-6-methyl-1,3,5-)riazin-2-yl)- amino)-carbonyl]-amino]-sulfonyl l-benzoic acid or its methyl Ester (METSULFURON); N,N-hexamethylenethiocarbamine S-ethyl acid (MOLINATE); 1-(3-trifluoromethylphenylphenyl NORFLURAZO)-4-methylamino-5-chloro-6-pyridazone (NORFLURAZO) N); 4-(di-n-propylamino)-3,5-dinitrobenzenesulfo amide (ORYZALIN); 2-chloro-4-trifluoromethylphenylene -3-Ethoxy-4-nitro-phenyl ether (OXYFLUORFEN) :N-(1-methylene o Hill)-3,4-dimethyl-2,6-sinitroani Phosphorus (PENDIMETHALIN); N-(3'-methylphenyl)-carba 3-(ethoxycarbonylaminophenyl) mic acid (PHENMEDIPHAM) ); α-chloro-2',6'-diethyl-N-(2-propoxyethyl)-acetate toanilide (PRETI LACHLOR); 2-chloro-N-isopropyla Cetanilide (PROPACHLOR); Isopropyl N-phenylcarbamate PROPHAM; 0-(6-chloro-3-phenyl-pyridazin-4-y ) S-octylthiocarbonate (PYRIDATE); 2-T4- (6 -chloroquinoxalin-2-yl-oxy)-phenoxy]-ethyl propionate 2-[1-(ethoxyamino) -butylidene]-5-(2-ethylthiopropyl)-1,3-cyclohexadi SETHOXYDIM; 2-chloro-4,6-bis-(ethylamino)- 1,3,5-triazine (S IMAZ INE); 2,4-bis-[N-e tylaminoco-6-methylthio-1,3,5-triazine (S IMETRYN ); 4-ethylamino-2-t-butylamino-〇-methylthio 8-tria TERBUTRYN; 3-[[[(4-methoxy-6-methyl- 1,3,5-triazin-2-yl)-amino]-carbonyl]-amino]-su Methyl sulfonylcorchioffene-2-carboxylate (THIAMETURON); N,N-diethylthiocarbamic acid S-[(4-chlorophenyl)-methyl] (THIOBENCARB); N,N-diisopropylthiocarbamic acid S-( 2゜3.3-)trichloroallyl) (TRIALLATE); 2.6-sinitro 4-Trifluoromethyl-N,N-dipropylaniline (TRIFLURAL) IN). Surprisingly, some mixtures also exhibit synergistic effects.

Also other known active compounds such as fungicides, Insecticides, acaricides , nematicides, small bird repellents, plant nutrients and soil amendments. Mixtures with good agents are possible.

The active compounds may be used as such or in the form of their formulations or further from their formulations. Use forms prepared by dilution, such as liquid preparations, suspensions, emulsions, powders, liniments, and It can be used in the form of granules. These things are done in the usual way, e.g. Watering, spraying, atomizing ng) or by granule scattering.

The active compounds according to the invention can be applied before or after germination of the plants.

The compounds can also be mixed into the soil before sowing seeds.

The amount of active compound used can vary within a substantial range. This amount is essentially depends on the nature of the desired effect. In general, the application rate is between 1 g and 10 kg of the compound, preferably between 5 g and 5 kg/ha.

The preparation and use of the active compounds according to the invention can be learned from the following examples.

[Example 1] [Step (a)] 18.9 g of 1-(4-methylphenyl-3-butyl) isocyanate (0°1 mole) ), 1=methyl-5-ethyl-methylamino-1,2-dihydro-3H-1 , 15.6 g (0.1 mol) of 2,4-triazol-3-one and acetonitrile 250 m1 and 1,8-diazabicyclo-[5,4,01-undes After adding 5 drops of -7-ene (DBU), the reaction mixture was stirred at room temperature for 2 hours. melt The liquid was concentrated under a water pump vacuum and the residue was chromatographed on silica gel. (eluent dichlorohexane/ethyl acetate 1.1).

2-[4-(4-methyl-phenyl)-boudo-2-ylaminocarbonyl]- 1-Methyl-5-ethyl-methylamino-1,2-dihydro-3H-1,2,4 28 g (81% of theory) of -triazol-3-one were obtained with the oil.

'HNMR (CDCI3/TMS): δ=1.20-1.23: 1.24- 1.30 + 2.30: 2.56-2.66: 3.10: 3.3 0; 7.05; 8.05-8. O7ppm [Example 2] [Step (b)] 4.4 g (25 mmol) of 1-(4-ethylphenyl)-3-butylamine and A mixture of 2.6 g (25 mmol) of triethylamine was added to 2-chlorocarbonyl- 5-dimethylamino-1-ethyl-1,2-dihydro-3H-1,2゜4-tri A mixture of 5.5 g (25 mmol) of azol-3-one and 150 ml of acetonitrile. It was added dropwise to the mixture. During this step, the temperature of the reaction mixture rose to 33°C. . The mixture was stirred at room temperature for 2 hours and then filtered.

The filtrate was evaporated under water pump vacuum and the residue was extracted with methylene chloride/water. , the organic phase was dried using sodium sulfate, filtered, and the solvent was removed using a water jet pump. Removed by distillation under vacuum. The residue was chromatographed on silica gel. (Eluent dichlorohexane/ethyl acetate 1:1).

2-[4-(4-ethylphenyl)-budo-2-yluaminocarbonyl]- 1-ethyl-5-dimethylamino-1,2-dihydro-38-1,2,4-tri 4.9 g (55% of theory) of azol-3-one were obtained as an oil.

'HNMR (CDCIs/TMS): δ=1.00-. 05.120-1.26 : 2.60-2.70; 3.18; 3.82-3.90; 3. 90-4.00; 7.10; 8.112-8-16pp Same as Examples 1 and 2 Formula (I) which can be prepared and according to the general description of the process according to the invention Other examples of compounds are shown in Table 1 below.

Starting material of formula (II): [Example (II-1)] 35 g (0.5 mol) dimethyl cyanamide and 156 g phenyl chloroformate ( 1.0 mol) was stirred at 100° C. for 16 hours. then volatilizes more easily The components are removed by distillation under water pump vacuum (bath temperature: 80 °C) and the oil The residue was distilled under oil-pump vacuum.

N,N-dimethyl-N with boiling point range 158-165 °C 10.5-0.8 mbar '-Phenoxycarbonyl-chloroformamidine 61.4 g (54% of theory) )was gotten.

A solution of 6.9 g (0.15 mol) of methylhydrazine in 100 ml of dioxane N,N-dimethyl-N'-phenoxycarbonyl at 20-30°C (cooling required) -Chloroformamidine 17.0g (0,075 mol) and methylene chloride 1 00ml of the mixture was added dropwise. The reaction mixture was stirred at 20°C for 4 hours, Then it was filtered. The solvent is removed from the filtrate by distillation under the vacuum of a water pump, and The liberated phenol was removed by distillation under oil-pump vacuum.

5-dimethylamino-1-methyl-1,2-dihydro-3H-1,2,4-1- 9.8 g (92% of theory) of lyazol-3-one were obtained as an oily residue.

Density HNMR (DMSO-d6, δ, pp+*): 3.20; 3. 45.

The product was crystallized by boiling with acetonitrile; mp = 22 2℃.

[Example (II-2)] 73 g (0.5 mol) of ethyl 2-isopropylhydrazinecarboxylate and carbonated water 42 g (0.5 mol) of sodium chloride in 200 ml of methylene chloride and 400 ml of water introduced inside. 55 g (0.52 mol) of cyanodiene bromide were stirred at room temperature. (Requires cooling). After stirring for an additional 3 hours, the evolution of CO7 ceased. Yes The organic phase was separated using a separatory funnel, dried over sodium sulfate and concentrated in vacuo. Shrunk.

73 g of ethyl 2-propyl-2-cyanohydrazinecarboxylate (theoretical value of 85. 4%) was obtained as a residue in the form of a thin oil.

'HNMR: (CDC13, δ, ppm) 1.25-1.30; 1.3 0-1°35+3.5-3.65; 4.20-4.30°2-propyl-2-sil 35 g (0.2 mol) of ethyl anohydrazinecarboxylate in absolute ethanol It was added dropwise to a solution of 100 ml of 3% dimethylamine. Bring the solution to room temperature first The mixture was stirred for 8 hours at reflux temperature and then for 1.5 hours at reflux temperature. After concentrating in vacuo, An oily residue remained which gradually crystallized upon standing. Cyclohexane/ethyl acetate ( 5-dimethylamino-1-iso with a melting point of 111°C. Propyl-1,2-dihydro-3H-1,2,4-triazol-3-one 30g (88% of theory).

Compounds of formula (II) which can be prepared analogously are, for example, those shown in Table 2 below: II 3 C2H5CJs CHs 89II 4 CHzCHz 0-CHz CHt CHs 183II5 (CJ)4CH3 (amorphous) II6 (CH2)5 CH3 (amorphous) II7 CH (CH3)2 C1 ( CHs)z CHs 11.9II-8CH3c, n, CH3 (amorphous) II 8 CH3CH3C188 Starting material of formula (III).

[Example (III-1)] 150 g of phosgene (i, 5 mol) was introduced into 2.5 l of chlorobenzene at 15°C. and 1. chlorobenzene in this solution. 1,1-dimethyl-3-( in C1 235 g (1.0 mol) of 4-ethoxycarbonyl-phenyl)-propylamine The solution was metered in dropwise with stirring, during this process the internal temperature reached approximately 25°C. Rose. The reaction mixture is then heated to about 70°C, stirred and further immersed in phosgene. gradually heating to reflux temperature (about 127° C.) while passing (about 50 g/hour), and After 30 minutes it was treated with phosgene under reflux. About 11 chlorobenzene with excess phosge was removed from the clear solution by distillation. Finally, pump the mixture into a water pump. It was evaporated under vacuum and the residue was distilled under oil-pump vacuum.

1,1-dimethyl-3-(4- 253 g of ethoxycarbonyl-phenyl)-propylisocyanate (theoretical value) 97%) was obtained.

Other examples of compounds of formula (III) that can be produced in the same manner as Example (III-1) are as follows: Table 3 shows: R4-N=C=X (III) Table 3 - continued H3 Starting material of formula (IV): [Example (IV-1)] 5-dimethylamino-1-methyl-1,2-dihydro-3H-1,2,4-1- Mixture of 71 g (0.5 mol) of lyazol-3-one and 800 ml of acetonitrile Heat the material to reflux temperature while passing it through phosgene, and the evolution of hydrogen chloride stops. treated with phosgene. Subsequently blow nitrogen into the mixture and then carefully drain the solvent. and left. The residue was recrystallized from ethyl acetate.

2-chlorocarbonyl-5-dimethylamino-1-methyl, melting point 98-100°C -1,2-dihydro-3H-1,2,4-triazol-3-one 88 g (theoretical value 86%) was obtained.

'HNMR(CDC]3/TMS): 6=3.20; 3.28ppm.

Starting material of formula (V): [Example (V-1) 96.7 g (0.50 mol) of 1-bromo-2-chlorobenzene and 3-amino 45.7 g (0.55 mol) of no-3,3-dimethyl-1-propyne was The mixture was introduced into 500 ml of Ruamine. Palladium(II) dichloride-bis(triphene) Nylphosphine) 7.0g (0.01 mol), paulownia (I) iodide 7゜6g ( 0.04 mol) and 21.0 g (0.4 mol) of triphenylphosphine were added, The reaction mixture was then refluxed for 24 hours. The mixture is then filtered and the filtrate is washed with water. Evaporated under pump vacuum. The residue was mixed with methylene chloride/water (approximately 300ml/ 300ml), separate the organic phase, and extract using sodium sulfate. dried and filtered. The solvent is removed from the filtrate by distillation under the vacuum of a water jet pump. removed and the remaining crude product purified by distillation under oil-pump vacuum. did.

3-amino-3,3-dimethyl-1-(2 74.1 g (75% of theory) of -chloro-phenyl)-1-propyl were obtained. .

[Example (V-2)] In a Parr hydrogenation unit, 3-amino-3,3-dimethyl-1-( 96.8 g (0.50 mol) of 4-chloro-phenyl)-1-propyl was added to tetra Mixed with 400ml of hydrofuran and Lindlar catalyst (5% palladium on calcium carbonate, immersed in lead) 13.0 g was added. Then the total The mixture was stirred until the calculated hydrogen uptake (1 molar equivalent after about 15 hours) was completed. Shake under 3 bar hydrogen pressure at a temperature gradually increasing from 25°C to 50°C. . The mixture was then filtered, the filtrate was evaporated under water pump vacuum, and the remaining crude The product was purified by distillation under oil-pump vacuum.

3-amino-3,3-dimethyl-1-(4 67.5 g (69% of theory) of -chloro-phenyl)-1-propene were obtained. .

[Example (V-3)] In a stirred autoclave, 3-amino-3,3-dimethyl-1-(2-chloride) 40.6 g (0.21 mol) of lolo-phenyl)-1-propyne was added to tetrahydrochloride. It was mixed with 250 ml of furan, stirred, and 10 g of Raney nickel was added. Next, hydrogen was metered in to a pressure of 50 bar and the mixture was gradually heated to 25° with stirring. Heated from C to 40'C. The hydrogen pressure is lowered to 40 bar each time, and the pressure remains constant. It was readjusted to 50 bar until it reached . The mixture is then filtered and the filtrate is pumped with a water jet. Evaporate under vacuum and the remaining crude product distilled under oil-pump vacuum. Ta.

3-amino-3,3-dimethyl-1-(2 31.8 g (77% of theory) of -chloro-phenyl)-propane were obtained.

Mission type; In the following usage examples, the following compound (A) was used as a comparison substance: 2-phenylene Ruaminocarbonyl-5-morpholino-1,2-dihydro-3H-1,2,4- triazol-4-one (Disclosed in German Patent Application No. 2.042.660, Example 10).

[Example A] Post-germination test Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether as appropriate for the active compound. To produce the preparation, 1 part by weight of the active compound is mixed with the above amount of solvent and of emulsifier was added and the concentrate was diluted with water to the desired concentration.

Test plants with a height of 5 to 15 cm are treated with a specified amount of the desired active compound per unit area. The active compound preparation was sprayed as used. Activate desired concentration of spray liquid A specific amount of the compound is selected to be applied as 20,001 liters of water per hectare. Ta. After 3 weeks, the degree of damage to the plants was compared to the growth of untreated controls and the percentage damage was determined. and evaluated. The numbers represent the following meanings: Same as untreated control without double effect) 100% = all eradicated When used at an application rate of 500 g/ha, the compounds of the following production examples Millet, Economia, and Abies, with remarkable tolerance in locosi and soybeans. up to 100% active against the spp. Showed gender: 1.3.4.5.6.7.8.9.1o, 11.12.13.15 ．． 18.20.22.23.26.27.30.63.64.65.67.69 ．． 74.77.81.91.92.96.98.101.110.111.11 2.114.116.119.122.123.125 and 127° comparative compounds (A) showed no activity against the above weeds.

[Example B] Pre-emergence test Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether, suitable amount of active compound. To produce the preparation, 1 part by weight of the active compound is mixed with the above amount of solvent and of emulsifier was added and the concentrate was diluted with water to the desired concentration.

The seeds of the test plants are sown in normal soil and after 24 hours the active compound preparation is applied as a solution. Spread. It is appropriate to keep the amount of water per unit area constant. in the preparation The concentration of active compound in is not important, only the amount of active compound applied per unit area will be decided. After 3 weeks, the degree of damage to the plants was compared to the growth of untreated controls. It was evaluated as % damage.

The numbers mean: 0% = no effect, same as untreated control) 100% = total eradication Using an application rate of 1000 g/ha, the compounds of the following production examples were applied to barley, corn With remarkable tolerance in sorghum and soybean, Showed up to 100% activity against Quercus sp. and Portulaca sp.=7.9.12.6 5 and 67° Comparison substances (A) are sweet potato (30%) and Portulaca (50%) %).

The formulas of the compounds of general formula (1) according to the present invention used for the usage examples are shown below. , and give the number of manufacturing examples (“Example No., J”).

Continuation of front page (51) tnt, C1,5 identification symbol Internal office reference number C07D413/12 249 7602-4C417/12 249 9051-4C (72) Inventor Koenig, Klaus Federal Republic of Germany Day 5068 Opental Zumhanenberg 40 (72) Inventor Lürssen, Klaus Day 5060 Bergitz Shugratbatscha 2/Augustokirsperustrasse 145 I (72) Inventor Zantel, Hassis Joachim Day 5090 of the Federal Republic of Germany -Ferkusen Grünstrasse 9A (72) Inventor Schmidt, Robert Earl Day 5060 of the Federal Republic of Germany Bergischjugratbach 2 Imwaldwinkel 110

Claims (8)

[Claims] 1. General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼In formula (I), R1 and R2 are mutually independent. In each case alkyl, alkenyl, alkynyl, halogenoalkyl, halogeno alkenyl, halogenoalkynyl, cyanoalkyl, alkoxyalkyl, alkyl koxy, cycloalkyl, cycloalkylalkyl, optionally substituted in each case Aryl, aralkyl or heteroaryl, which may be together with the nitrogen atom to which is bonded represents an optionally substituted heterocycle, R3 represents alkyl or cycloalkyl, R4 represents alkyl, alkenyl, Alkynyl, halogenoalkyl, halogenoalkenyl, halogenoalkynyl, Anoalkyl, hydroxyalkyl, alkoxyalkyl, aryloxyalkyl Kyl, arylthioalkyl, arylsulfinylalkyl, arylsulfonyl Nylalkyl, arylaminoalkyl, N-alkyl-arylaminoalkyl arylazoalkyl, alkoxycarbonylalkyl, alkoxycarbo nylalkenyl, alkylaminoalkyl, dialkylaminoalkyl, each optionally substituted cycloalkyl, cycloalkylalkyl, represents chloroalkenyl or cycloalkenylalkyl or optionally substituted optionally substituted heterocyclic alkyl, in each case optionally substituted aralkyl , arylalkenyl, arylalkynyl, aroyl, aryl, aralkyl represents oxy or aryloxy, or alkoxy, alkenyloxy or represents alkynyloxy, and X represents oxygen or sulfur, Substituted triazolinones. 2. R1 and R2 are each independently in each case straight-chain or branched carbon; Alkyl having 1 to 8 atoms, alkenyl having 2 to 8 carbon atoms, carbon alkynyl having 2 to 8 atoms, 1 to 8 carbon atoms and the same or different halogenoalkyl having 1 to 17 halogen atoms, each having 2 to 8 carbon atoms and Halogen having 1 to 15 or 1 to 13 identical or different halogen atoms noalkenyl or halogenoalkynyl, 1 carbon atom in each individual alkyl moiety Cyanoalkyl, alkoxyalkyl or alkoxy having ~6 carbon atoms cycloalkyl having 3 to 7 children, 3 to 7 carbon atoms in the cycloalkyl moiety; and cycloalkylalkyl having 1 to 6 carbon atoms in the alkyl moiety , or 6 to 10 carbon atoms in the aryl part and 1 to 6 carbon atoms in the alkyl part aralkyl having 6 to 10 carbon atoms or aryl having 6 to 10 carbon atoms or 2 carbon atoms ~9 and heteroatoms, in particular 1 to 3 nitrogen, oxygen and/or sulfur represents loweryl, each of these substituents being the same or different as the case may be; It may be mono- or polysubstituted with substituents, wherein the appropriate substituents in each case are are halogen, cyano, nitro, each having 1 to 4 carbon atoms and, if appropriate, the same or linear or branched in each case with 1 to 9 different halogen atoms. Chain alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoal oxy or halogenoalkylthio, or R1 and R2 are also together with the nitrogen atom to which it is attached, if appropriate further heteroatoms, especially nitrogen, acid may contain 1 to 2 elements and/or sulfur, and may be the same or different as appropriate It may be substituted with one or two substituents, and in this case, suitable substituents include halogen. and 1 to 4 carbon atoms each, and if appropriate 1 identical or different halogen atom. ~9, and also linear in each case with 1 to 2 oxo or thiono groups or a 5- to 10-membered heterocycle with branched alkyl or halogenoalkyl. Representation, R3 is straight-chain or branched alkyl or carbon having 1 to 8 carbon atoms; represents cycloalkyl having 3 to 8 atoms, if R4 is in each case linear or branched alkyl having 1 to 18 carbon atoms, or branched alkyl having 2 to 8 carbon atoms; alkenyl having 2 to 8 carbon atoms, alkynyl having 1 to 8 carbon atoms and halogenoalkyl having 1 to 17 identical or different halogen atoms, each 2 to 8 carbon atoms and 1 to 15 same or different halogen atoms or 1 to 8 carbon atoms halogenoalkenyl or halogenoalkynyl having 13 carbon atoms 1 to 8 cyanoalkyl having 1 to 8 carbon atoms and 1 to 6 hydroxyl groups represents hydroxyalkyl having 1 to 4 carbon atoms in each alkyl moiety phenoxyalkyl, phenylthioalkyl, phenylsulfinylalkyl phenylsulfonylalkyl, phenylaminoalkyl, N-(C1-C4 -alkyl)-phenylaminoalkyl or phenylazoalkyl , alkoxyalkyl, alkoxyalkyl, having up to 6 carbon atoms in each individual alkyl represents koxycarbonylalkyl or alkoxycarbonylalkenyl, alkylaminoalkyl having 1 to 6 carbon atoms in each individual alkyl moiety or dialkylaminoalkyl, respectively cycloalkyl or cyclo 3 to 8 carbon atoms in the alkenyl moiety and 1 to 8 carbon atoms in the alkyl moiety, if appropriate. 6, and may optionally be substituted with 1 to 3 substituents, the same or different. Suitable substituents include in each case halogen, cyano, phenyl and 1 to 4 carbon atoms and, if appropriate, 1 to 9 identical or different halogen atoms straight-chain or branched alkyl or halogenoalkyl in each case with and 1 to 4 carbon atoms and 1 to 5 same or different halogen atoms. straight-chain or branched halogenoalkenyl having 4 carbon atoms each A system in which there is a divalent alkanediyl or alkenediyl in each case with up to Chloalkyl, cycloalkylalkyl, cycloalkenyl or cycloalke Represents nyl alkyl; R4 is further a linear or branched alkyl moiety 1 to 6 carbon atoms and 2 to 9 carbon atoms and heteroatoms in the heterocyclic moiety, especially containing 1 to 3 nitrogen, oxygen and/or sulfur, and from time to time in the same or different locations. It may be mono- or polysubstituted with substituents, in which case suitable substituents include halogen, cyano, nitro and each with 1 to 5 carbon atoms and, if appropriate, the same or different in each case straight-chain or branched alkyl having 1 to 9 halogen atoms; alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halo represents a heterocyclic alkyl with genoalkylthio or alkoxycarbonyl or; R4 is further in each case linear or branched and has 1 to 8 carbon atoms; alkoxy, alganyloxy having 2 to 8 carbon atoms or 2 carbon atoms alkynyloxy having ~8 or 6 to 10 carbon atoms in each aryl moiety 1 to 8 carbon atoms in the straight-chain or branched alkyl moiety, if appropriate. carbon atoms in a straight-chain or branched alkenyl or alkynyl moiety In this case, the hydrogen atom of the α carbon atom is replaced by ethane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl or propane-1,5-diyl yl, each optionally substituted with 1 to 3 substituents of the same or different substituents where appropriate alkyl substituents include halogen and silicon, as appropriate. ano, and suitable aryl substituents include in each case halogen, cyano, Nitro, amino, hydroxyl, each with 1 to 6 carbon atoms in the alkyl moiety and as appropriate Then, in each case linear chain with 1 to 9 same or different halogen atoms or branched alkyl, alkoxy, alkylthio, halogenoalkyl, Halogenoalkoxy, halogenoalkylthio, alkylsulfinyl, alkyl Sulfonyl, halogenoalkylsulfinyl, halogenoalkylsulfonyl, a Lucanoyl or alkoxycarbonyl, cycloalkyl having 3 to 6 carbon atoms alkanyl, oxaalkanediyl and phenoxy having up to 5 carbon atoms. ralkyl, arylalkenyl, arylalkynyl, aroyl, aryl, aryl represents ralkyloxy or aryloxy; or R4 is a phenyl moiety represents benzyl with a fused -O-CH2-O- group, and X represents oxygen or sulfur, A substituted triazolinone of general formula (I) according to claim 1. 3. R1 and R2 are each independently methyl, ethyl, n- or i-propyl, n-, i-, S- or t-butyl, n- or i-pentyl allyl, allyl, propargyl, in each case linear or branched; 1 to 4 carbon atoms having 1 to 9 same or different halogen atoms; halogenoalkyl having 3 to 6 carbon atoms or represents halogenoalkynyl having 3 to 6 carbon atoms, cyanoethyl, meth oxymethyl, methoxyethyl, methoxy, ethoxy, cyclopropyl, cyclopyl Lopylmethyl, cyclopentyl, cyclohexyl, cyclohexylmethyl, cyclo represents lohexylethyl, cyclopentylmethyl, each of which is the same or different as the case may be. It may be substituted with 1 to 3 different substituents, and in this case, suitable substituents include fluorine. , chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, methylthio, tri Bases with fluoromethyl, trifluoromethoxy or trifluoromethylthio represents phenyl, phenylethyl or phenyl, or R1 and R2 together with the nitrogen atom to which they are bonded are each the same as the case may be; Alternatively, it may be substituted with 1 to 3 different substituents, in which case an appropriate substituent methyl, ethyl, n- or i-propyl, chlorine or trifluoromethyl expression with ▲There are mathematical formulas, chemical formulas, tables, etc.▼;▲There are mathematical formulas, chemical formulas, tables, etc.▼;▲Numbers There are formulas, chemical formulas, tables, etc. ▼; ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼; ▲ Mathematical formulas, There are chemical formulas, tables, etc.▼;▲There are mathematical formulas, chemical formulas, tables, etc.▼;▲Mathematical formulas, chemistry There are formulas, tables, etc.▼;▲There are mathematical formulas, chemical formulas, tables, etc.▼;▲Mathematical formulas, chemical formulas, There are tables, etc. ▼; ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ Mathematical formulas, chemical formulas, tables, etc. etc. represents the heterocycle of ▼, R3 is methyl, ethyl, propyl, isopropyl, n-, i-, s- or t -butyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexy represents the R4 is methyl, ethyl, n- or i-propyl, n-, i-, s- or tert-butyl, in each case linear or branched pentyl, hexyl, hepyl Representing tyl, octyl, nonyl, decyl, dodecyl, or allyl, in each case Straight-chain or branched butenyl, pentenyl or hexenyl, propargyl linear or branched butenyl, pentenyl or hexyl in each case 1 to 8 carbon atoms and the same or different halogen atoms, especially fluorine, Straight-chain or branched halogenoalkyl having 1 to 9 chlorine or bromine, each having 3 to 8 carbon atoms and 1 to 3 halogen atoms, especially fluorine or chlorine in each case a straight-chain or branched halogenoalkenyl or halogenoalkyl; ruquinyl, in each case having 1 to 6 carbon atoms in the alkyl moiety, linear or is a branched cyanoalkyl having 1 to 6 carbon atoms and 1 to 3 hydroxyl groups. hydroxyalkyl having a carbon atom in each individual alkyl or alkenyl moiety alkoxyalkyl, alkoxycarbonylalkyl or alkoxycarbonylalkyl having up to 4 children; Alkoxycarbonylalkenyl, alkylaminoalkyl or dialkyl represents aminoalkyl or each optionally with the same or different substituents 1- It may also be tri-substituted, with suitable substituents including fluorine, chlorine in each case. , bromine, methyl, ethyl, n- or i-propyl, n-, i-, S- or is t-butyl, cyano, methanediyl, ethanediyl, butanediyl or Cyclopropyl, cyclopropylmethyl, cyclopropyl with tadienediyl Ethyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclohexylmethyl, cyclohexylethyl, cyclohexenyl or cyclohexyl Represents xenylmethyl or dichloroallyl; R4 further optionally each has 1 to 3 substituents which are the same or different in the heterocyclic moiety; Appropriate heterocycles may be substituted, in each case a group ▲ mathematical formula, chemical formula, table, etc. There are ▼；▲There are mathematical formulas, chemical formulas, tables, etc.▼;▲There are mathematical formulas, chemical formulas, tables, etc. ▼;▲There are mathematical formulas, chemical formulas, tables, etc.▼;▲There are mathematical formulas, chemical formulas, tables, etc. ▼;▲There are mathematical formulas, chemical formulas, tables, etc.▼;▲There are mathematical formulas, chemical formulas, tables, etc.▼ ;▲There are mathematical formulas, chemical formulas, tables, etc.▼;▲There are mathematical formulas, chemical formulas, tables, etc.▼;▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ , where Z represents in each case oxygen or sulfur, and the appropriate substituents are fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or is i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, Methylthio, trifluoromethyl, trifluoromethoxy or trifluoromethane Represents heterocyclic methyl, heterocyclic propyl or heterocyclic ethyl with tilthio. R4 is further in each case a straight-chain or branched carbon atom having 1 to 6 carbon atoms; alkoxy, alkenyloxy having 3 to 6 carbon atoms or 3 carbon atoms represents an alkynyloxy group having ~6 or each the same or different as the case may be; may be substituted with 1 to 3 substituents, in which case, suitable phenyl substituents include In each case fluorine, chlorine, bromine, hydroxyl, cyano, nitro, methyl, thyl, n- or i-propyl, n-, i-, s- or t-butyl, meth xy, ethoxy, methylthio, difluoromethyl, trifluoromethyl, diflu olomethoxy, trifluoromethoxy, trifluoromethylthio, trifluoro Methylsulfinyl, trifluoromethylsulfonyl, methylsulfinyl, Tylsulfonyl, acetyl, propionyl, methoxycarbonyl, ethoxycal Bonyl, n- or i-propoxycarbonyl, cyclohexyl or phenol benzyl, phenyl ethyl, which may be linear or branched, phenylpropyl, phenylpropenyl, phenylprovinyl, phenylbutylene Chil, phenylbutenyl, phenylbutenyl, phenylpentyl, phenyl pen thenyl, phenylpentenyl, phenylhexyl, phenylhexenyl, phenyl Ruhexinil, phenylheptyl, phenylheptenyl, phenylheptenyl, Phenyl octyl, phenyl octenyl, phenyl octenyl, phenyl cyano Methyl, phenylcyanoethyl, phenylcyanopropyl, benzyloxy, enylethyloxy, phenoxy, phenoxyethyl, phenoxypropyl, Enoxy-i-propyl, phenoxyisobutyl, phenoxy-t-butyl, phenoxy-i-propyl, phenoxy-isobutyl, phenoxy-t-butyl, enylthioisobutyl, phenylthio-t-butyl, phenylthioethyl, fe nylthiopropyl, phenylthio-i-propyl, benzoyl or naphthyl and X represents oxygen or sulfur A substituted triazolinone of general formula (I) according to claim 1. 4. If R1 is methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n- or i-pentyl, cyclopropyl, cyclopentyl or cyclohexyl and R2 is methyl, ethyl, n- or i-propylene represents pyru, n-, i-, s- or t-butyl, n- or i-pentyl Watermelon, R1 and R2 together with the nitrogen atom to which these things are bonded form the formula ▲ Formula , chemical formulas, tables, etc. ▼; ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼; ▲ Mathematical formulas, chemical formulas, etc. There are scientific formulas, tables, etc. ▼; ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ Mathematical formulas, chemistry There are formulas, tables, etc.▼ represents the heterocycle of R3 represents methyl, ethyl, propyl or isopropyl, especially methyl; R4 may be optionally substituted with 1 to 3 substituents, each of which is the same or different; Suitable phenyl substituents include in each case fluorine, chlorine, bromine, methyl, ethyl, chill, n- or i-propyl, n-, i-, s- or t-butyl, tri- Fluoromethyl, phenyl, methoxy, ethoxy, propoxy, isopropoxy , difluoromethoxy, trifluoromethoxy, difluoromethyl, methoxyca Rubonyl, ethoxycarbonyl, propoxycarbonyl, cyano, methylthio, Ethylthio, propylthio, isopropylthio, difluoromethylthio, trifium fluoromethylthio, methylsulfinyl, methylsulfonyl and trifluoromethane 1-methyl-3-phenyl-propyl, 1-ethyl-3- with thylsulfonyl Phenyl-propyl, 1-propyl-3-phenyl-propyl, 1-isopropyl -3-phenyl-propyl, 2-methyl-3-phenyl-propyl, 1,1- Dimethyl-3-phenyl-propyl, 1-methyl-1-ethyl-3-phenyl- Propyl, 1,1-diethyl-3-phenyl-propyl, 1-methyl-1-propyl Pyl-3-phenyl-propyl, 1-methyl-3-phenyl-2-propenyl, 1-ethyl-3-phenyl-2-propenyl, 1-propyl-3-phenyl-2 -propenyl, 1-isopropyl-3-phenyl-2-propenyl, 1,1-di Methyl-3-phenyl-2-propenyl, 1-methyl-1-ethyl-3-pheny -2-propenyl, 1,1-diethyl-3-phenyl-2-propenyl, 1- Methyl-1-propyl-3-phenyl-2-propenyl, 1-methyl-3-phenylene Nyl-2-provinyl, 1-ethyl-3-phenyl-2-provinyl, 1-provinyl Pyl-3-phenyl-2-provinyl, 1-isopropyl-3-phenyl-2- Propynyl, 1,1-dimethyl-3-phenyl-2-propynyl, 1-methyl- 1-ethyl-3-phenyl-2-provinyl, 1,1-diethyl-3-phenyl -2-provinyl, 1-methyl-1-propyl-3-phenyl-2-provinyl , 1,2-dimethyl-3-phenyl-propyl, 2-ethyl-1-methyl-3- Phenyl-propyl, 1,2,2-trimethyl-3-phenyl-propyl, 1, 3,3-trimethyl-3-phenyl-propyl or 1,1,2,2-tetrameth represents thyl-3-phenyl-propyl, and X represents oxygen A substituted triazolinone of general formula (I) according to claim 1. 5. General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼In formula (I), R1 and R2 are mutually independent. In each case alkyl, alkenyl, alkynyl, halogenoalkyl, halogeno alkenyl, halogenoalkynyl, cyanoalkyl, alkoxyalkyl, alkyl koxy, cycloalkyl, cycloalkylalkyl, optionally substituted in each case Aryl, aralkyl or heteroaryl, which may be together with the nitrogen atom to which is bonded represents an optionally substituted heterocycle, R3 represents alkyl or cycloalkyl, R4 represents alkyl, alkenyl, Alkynyl, halogenoalkyl, halogenoalkenyl, halogenoalkynyl, Anoalkyl, hydroxyalkyl, alkoxyalkyl, aryloxyalkyl Kyl, arylthioalkyl, arylsulfinylalkyl, arylsulfonyl Nylalkyl, arylaminoalkyl, N-alkyl-arylaminoalkyl arylazoalkyl, alkoxycarbonylalkyl, alkoxycarbo nylalkenyl, alkylaminoalkyl, dialkylaminoalkyl, each optionally substituted cycloalkyl, cycloalkylalkyl, represents chloroalkenyl or cycloalkenylalkyl or optionally substituted optionally substituted heterocyclic alkyl, in each case optionally substituted aralkyl , arylalkenyl, arylalkynyl, aroyl, aryl, aralkyl represents oxy or aryloxy, or alkoxy, alkenyloxy or represents alkynyloxy, and X represents oxygen or sulfur, When producing a substituted triazolinone of a) general formula (II) ▲There are mathematical formulas, chemical formulas, tables, etc.▼In formula (II), R1, R2 and R3 are the above triazolinones and/or tautomers of these compounds, i.e. the corresponding hydroxytriazole, if appropriate in the presence of a reaction auxiliary and if appropriate For example, in the presence of a diluent, general formula (III) R4-N=C=X(III) Reacted with iso(thio)cyanate in which R4 and X have the above meanings. or b) General formula (IV) ▲There are mathematical formulas, chemical formulas, tables, etc.▼In the formula (IV), R1, R2 and R3 are the above a chlorocarbonyl-triazolinone with a meaning, if appropriate in the presence of an acid binder. of the general formula (V)H2N-R4(V) in the presence of a diluent and if appropriate a diluent. In the formula, R4 has the above meaning, General formula (I) according to claim 1, characterized in that it is reacted with an amine of A method for producing a substituted triazolinone. 6. at least one substituted triazolinone according to claim 1. A herbicide characterized by: 7. Substituted triazolinones of formula (I) according to claim 1 are undesirably undesirable plants characterized by their effects on plants and/or their environment; How to control things. 8. Substitution of formula (I) according to claim 1 in controlling undesirable plants Use of triazolinones.