SK495090A3 - Sulfonylaminocarbonyltriazolinones, method for their preparation, herbicidal agents them containing, and their use their use - Google Patents

Abstract

The invention relates to novel 2-sulphonylaminocarbonyl- 2,4-dihydro-3H-1,2,4-triazol-3-ones of the general formula (I) <IMAGE> in which R<1> represents hydrogen, hydroxyl, amino or an optionally substituted radical from the series comprising alkyl, alkenyl, alkynyl, cycloalkyl, aralkyl, aryl, alkoxy, alkenyloxy, alkylamino or dialkylamino, R<2> represents hydrogen, hydroxyl, mercapto, amino or an optionally substituted radical from the series comprising alkyl, cycloalkyl, cycloalkenyl, aralkyl, aryl, alkoxy, alkylamino or dialkylamino, and R<3> represents an optionally substituted radical from the series comprising alkyl, aralkyl, aryl or heteroaryl, and salts of compounds of the formula (I), to processes for their preparation, and to their use as herbicides.

Description

SULPHONYLAMINOCARBONYLTRIAZOLINONES, METHOD OF MANUFACTURE, HERBICIDALS OF THESE SUBSTANCE CONTAINING AND USE

Technical field

The invention relates to novel sulfonylaminocarbonyltriazolinones, to a process for their preparation, to herbicidal compositions containing them and to their use.

BACKGROUND OF THE INVENTION

It is known that certain substituted aminocarbonylimidazolinones, such as 1-isobutylaminocarbonyl-2-imidazolidinone (isocarbamide), have herbicidal properties (see R. Wegler, Chemie der Pflanzenschutz- und Schädlingsbekämp-funksmittel, vol. 5, p. 219, Springer). Verlag, Berlin Heidelberg-New York, 1977). However, the effect of these compounds is not satisfactory in all respects.

SUMMARY OF THE INVENTION

The present invention relates to novel sulfonylaminocarbonyltriazophinones of the general formula I

in which

R ¹ is hydrogen, hydroxy, amino, or by F, Cl, Br, cyano, alkoxy of 1 to 4 carbon atoms, alkylcarbonyl of 1

V344 / 94H to 4 carbon atoms in the alkyl moiety or C1 -C4 alkoxycarbonyl substituted C1 -C6 alkyl, in each case fluorine, chlorine and / or bromine substituted C3 -C8 alkenyl; (C-C alebo) or (Ciny-C alk alk) alkynyl, optionally fluorine, chlorine, bromine and / or (C až-C alky) alkyl substituted by C až-C cyk-cycloalkyl or fluoro, chloro, bromo, cyano, nitro, C 1 -C 4 alkyl, trifluoromethyl, C 1 -C 4 alkoxy and / or C 1 -C 4 alkoxycarbonyl substituted by C 1 -C 3 phenylalkyl alkyl, optionally fluorine, chlorine, bromine, ky an amino, nitro, C 1 -C 4 alkyl, trifluoromethyl, C 1 -C 4 alkoxy, fluorine and / or chlorine substituted C 1 -C 3 alkoxy, C 1 -C 4 alkylthio group, fluorine and / or (C1 -C3) alkylthio, (C1 -C4) alkylsulfinyl, (C1 -C4) alkylsulfonyl or (C1 -C4) alkoxycarbonyl substituted by phenyl, optionally fluorine, chlorine, cyano, phenyl, C 1 -C 4 alkoxy or C 1 -C 4 alkoxycarbonyl substituted by C 1 -C 6 alkoxy, C 3 -C 4 alkenyloxy, optionally fluoro, cyano, alkoxy C 1 -C 4 or alkoxycarbonyl (C 1 -C 4) -alkoxy substituted by C 1 -C 4 -alkylamino or (C 1 -C 4) -alkylamino;

V344 / 94H

R ² is hydrogen, hydroxy, mercapto, amino, or by F, Cl, Br, cyano, cycloalkyl having 3 to 6 carbon atoms, alkoxy of 1 to 4 carbon atoms or alkoxycarbonyl having 1 to 4 carbon atoms in the an alkoxy moiety substituted by a C 1 -C 6 alkyl group, optionally a fluorine atom, a chlorine atom, a bromine atom and / or a C 1 -C 4 alkyl group substituted by a C 3 -C 6 cycloalkyl group, a cyclohexenyl group, optionally a fluorine atom, an atom chlorine, bromine, cyano, nitro, C 1 -C 4 alkyl, trifluoromethyl, C 1 -C 4 alkoxy, and / or C 1 -C 4 alkoxycarbonyl in the alkoxy moiety substituted by C 1 -C 3 phenylalkyl carbon atom in the alkyl moiety, optionally fluorine atom, at chlorine, bromine, cyano, nitro, C 1 -C 4 alkyl, trifluoromethyl, C 1 -C 4 alkoxy, fluorine and / or chlorine substituted by C 1 -C 3 alkoxy, C 1 -C 4 alkylthio C 1 -C 3 alkylthio, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl and / or C 1 -C 4 alkoxycarbonyl in the alkoxy moiety substituted phenyl or optionally fluorine, chlorine, cyano, (C 1 -C 4) alkoxy or (C 1 -C 4) alkoxycarbonyl substituted by C 1 -C 6 alkoxy, (C 1 -C 4) alkylamino or C 1 -C 4 dialkylamino; 4 carbon atoms in the alkyl moieties, and

R ³ is a moiety of the formula

V344 / 94H

R ⁴ and R ⁵ are the same or different from each other and are hydrogen, fluorine, chlorine, bromine, iodine, nitro, C 1 -C 6 alkyl optionally substituted by fluorine, chlorine, bromine, cyano, carboxy, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkylaminocarbonyl, C 1 -C 4 dialkylaminocarbonyl, hydroxy, C 1 -C 4 alkoxy, formyloxy (C 1 -C 4) alkylcarbonyloxy, (C 1 -C 4) alkoxycarbonyloxy, (C 1 -C 4) alkylaminocarbonyloxy, (C 1 -C 4) alkylthio, (C 1 -C 4) alkylsulfinyl; alkylsulfonyl having 1 to 4 carbon atoms, dialkylamine an osulfonyl group having 1 to 4 carbon atoms in the alkyl moieties, a cycloalkyl group having 3 to 6 carbon atoms or a phenyl group; (C 2 -C 6) alkenyl optionally substituted by fluorine, chlorine, bromine, cyano, (C 1 -C 4) alkoxycarbonyl, carboxy or phenyl; (C 2 -C 6) alkynyl optionally substituted by fluorine, chlorine, bromine, cyano, (C 1 -C 4) alkoxycarbonyl, carboxy or phenyl; (C 1 -C 4) alkoxy optionally substituted by fluorine, chlorine, bromine, cyano, carboxy, (C 1 -C 4) alkoxycarbonyl, (C 1 -C 4) alkoxy,

V344 / 94H (C1-C4) alkylthio, (C1-C4) alkylsulphinyl or (C1-C4) alkylsulphonyl; (C 1 -C 4) alkylthio optionally substituted by fluorine, chlorine, bromine, cyano, carboxy, (C 1 -C 4) alkoxycarbonyl, (C 1 -C 4) alkylthio, (C 1 -C 4) alkylsulfinyl or (C 1 -C 4) alkylsulfonyl; (C 3 -C 6) alkenyloxy optionally substituted by fluorine, chlorine, bromine, cyano or (C 1 -C 4) alkoxycarbonyl; (C 2 -C 6) alkenylthio optionally substituted by fluorine, chlorine, bromine, cyano, nitro, (C 1 -C 3) alkylthio or (C 1 -C 4) alkoxycarbonyl; (C 3 -C 6) alkynyloxy, (C 3 -C 6) alkynylthio or -S (O) _P -R ⁶ , where p is 1 or 2; and

R ⁶ is C 1 -C 4 alkyl optionally substituted by fluorine, chlorine, bromine, cyano or C 1 -C 4 alkoxycarbonyl; (C 3 -C 6) alkenyl, (C 3 -C 6) alkynyl, (C 1 -C 4) alkoxy, (C 1 -C 4) alkoxyalkylamino, (C 1 -C 4) alkylamino, (C 1 -C 4) alkylamino -C 4 alkyl, phenyl or a radical of formula -NHOR ^7, wherein

R ⁷ is C 1 -C 12 alkyl optionally substituted by fluorine, chlorine, cyano, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, alkylsulfonyl

A V344 / 94H group having 1 to 4 carbon atoms, an alkylcarbonyl group having 1 to 4 carbon atoms in the alkyl moiety, an alkoxycarbonyl group having 1 to 4 carbon atoms in the alkoxy moiety, an alkylaminocarbonyl group having 1 to 4 carbon atoms in the alkyl moiety or a dialkylaminocarbonyl group 1-4 carbon atoms in the alkyl moieties; (C 3 -C 6) alkenyl optionally substituted by fluorine, chlorine or bromine; (C až-C) alkynyl, (C až-C cyk) cycloalkyl, (C až-C cyk) cycloalkyl-C alky-C alky-alkyl, (C až-Ceny) phenylalkyl (C až-Ceny), which is optionally substituted by fluorine, chlorine, nitro, cyano, (C1-C4) -alkyl, (C1-C4) -alkoxy or (C1-C4) -alkoxycarbonyl; benzhydryl or phenyl optionally substituted by fluorine, chlorine, nitro, cyano, C 1 -C 4 alkyl, trifluoromethyl, C 1 -C 4 alkoxy, C 1 -C 2 fluoroalkoxy, C 1 -C 1 alkylthio C 4 -C 4 trifluoromethylthio or C 1 -C 4 alkoxycarbonyl;

R ⁴ and / or R ⁵ are furthermore phenyl or phenoxy, C 1 -C 4 alkylcarbonylamino, C 1 -C 4 alkoxycarbonylamino, C 1 -C 4 alkylaminocarbonylamino, dialkylaminoC 1-6 alkylcarbonylamino up to 4 carbon atoms in the alkyl moieties or a group of formula -CO-R ⁸ , wherein

R ⁸ is C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 3 -C 6 cycloalkoxy, C 3 -C 6 alkenyloxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylamino alkyl,

V344 / 94H C 1 -C 4 alkoxy, C 1 -C 4 alkoxyalkylamino or C 1 -C 4 dialkylamino optionally substituted by fluorine and / or chlorine,

R ⁴ and / or R ⁵ are furthermore trimethylsilyl, thiazolinyl, C 1 -C 4 alkylsulfonyloxy, C 1 -C 4 dialkylaminosulfonylamino or -CH = NR ⁹ , wherein -CH = NR ⁹ ;

R &lt; ⁹ &gt; is optionally fluorine, chlorine, cyano, carboxy, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfinyl or C1-C4alkylsulfonyl substituted C1-C4alkyl up to 6 carbon atoms; optionally a fluorine or chlorine substituted benzyl group; optionally fluorine or chlorine substituted C 3 -C 6 alkenyl or C 3 -C 6 alkynyl; optionally fluorine, chlorine, bromine, (C 1 -C 4) alkyl, (C 1 -C 4) alkoxy, trifluoromethyl, trifluoromethoxy or trifluoromethylthio substituted phenyl; optionally fluorine and / or chlorine-substituted alkoxy of 1 to 6 carbon atoms, alkenoxy of 3 to 6 carbon atoms, alkyloxy of 3 to 6 carbon atoms, or benzyloxy; amino, (C 1 -C 4) alkylamino, (C 1 -C 4) dialkylamino, phenylamino, (C 1 -C 4) alkylcarbonylamino, (C 1 -C 4) alkoxycarbonylamino, (1-6C) alkylsulfonylamino a phenylsulfonylamino group optionally substituted by fluorine, chlorine, bromine or methyl;

R ³ is furthermore a group of the general formula

V344 / 94H where

R ¹⁰ represents a hydrogen atom or a C 1 -C 4 alkyl group,

R ¹¹ and R ¹² are the same or different and are hydrogen, fluorine, chlorine, bromine, nitro, cyano, (C 1 -C 4) alkyl optionally substituted by fluorine and / or chlorine, (C 1 -C 4) alkoxy which is optionally substituted by fluorine and / or chlorine, carboxy, (C1-C4) alkoxycarbonyl, dimethylaminocarbonyl, (C1-C4) alkylsulfonyl or (C1-C4) dialkylaminosulfonyl;

R ³ is furthermore a group of the general formula

, 14 where

R ¹³ and R ¹⁴ are the same or different and represent a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a nitro group, a cyano group, an alkyl group having 1 to 4 carbon atoms optionally substituted by fluorine and / or chlorine or an alkoxy group having 1 up to 4 carbon atoms optionally substituted by fluorine and / or chlorine;

then

R ³ represents a group of the general formula

V344 / 94H

where

R ¹⁵ and R ¹⁶ are the same or different from each other and are hydrogen, fluorine, chlorine, bromine, nitro, cyano, (C 1 -C 4) alkyl optionally substituted by fluorine and / or chlorine, (C 1 -C 4) alkoxy C 1 -C 4 alkyl optionally substituted by fluorine and / or chlorine, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl or C 1 -C 4 alkylsulfonyl optionally substituted by fluorine and / or chlorine a (C 1 -C 4) dialkylaminosulfonyl group or a (C 1 -C 4) alkoxycarbonyl group or a dimethylaminocarbonyl group;

then

R ³ represents a group of the general formula

where

R ¹⁷ and R ¹⁸ have the same or different meanings and are hydrogen, fluorine, chlorine, bromine, C 1 -C 4 alkyl optionally substituted by fluorine and / or bromine, C 1 -C 4 alkoxy and optionally substituted by fluorine and / or chlorine, furthermore denotes an alkylthio group having 1 to 4 carbon atoms, an alkylsulfinyl group having 1 to 4 carbon atoms

V344 / 94H or a (C1-C4) alkylsulfonyl group optionally substituted by fluorine and / or chlorine or a (C1-C4) dialkylaminosulfonyl group in the alkyl moieties;

then

R ³ represents a group of the general formula

where

R ¹⁹ and R ²⁰ are the same or different from each other and are hydrogen, fluorine, chlorine, bromine, cyano, nitro, (C 1 -C 4) alkyl optionally substituted by fluorine and / or chlorine, (C 1 -C 4) alkoxy to 4 carbon atoms optionally substituted by fluorine and / or. chlorine, (C 1 -C 4) alkylthio, (C 1 -C 4) alkylsulfinyl or (C 1 -C 4) alkylsulfonyl optionally substituted by fluorine and / or chlorine, (C 1 -C 4) dialkylaminosulfonyl, (C 1 -C 4) alkoxycarbonyl or dimethylaminocarbonyl; and

A represents oxygen, sulfur or the group NZ ¹ , wherein

Z ¹ is hydrogen, C 1 -C 4 alkyl optionally substituted by fluorine, chlorine, bromine or cyano, C 3 -C 6 cycloalkyl, benzyl, phenyl optionally substituted by fluorine, chlorine, bromine or nitro, C1 -C4 alkylcarbonyl

V344 / 94H carbon in the alkyl moiety, C 1 -C 4 alkoxycarbonyl or C 1 -C 4 dialkylaminocarbonyl;

then

R ³ represents a group of the general formula

where

R ²¹ and R ²² are the same or different from each other and are hydrogen, C 1 -C 4 alkyl, halogen, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy up to 4 carbon atoms,

Y ¹ is sulfur or NR ²³ , wherein

R ( ²³⁾ is hydrogen or (C1-C4) -alkyl; then

R ³ represents a group of the general formula

R 'where

344/94 H

R ²⁴ represents a hydrogen atom, a C 1 -C 4 alkyl group, a benzyl group, a quinolyl group or a phenyl group,

R ²⁵ represents hydrogen, halogen, cyano, nitro, C 1 -C 4 alkyl optionally substituted by fluorine and / or chlorine, C 1 -C 4 alkoxy optionally substituted by fluorine and / or chlorine, dioxolanyl or a (C 1 -C 4) alkoxycarbonyl group; and

R ²⁶ represents a hydrogen atom, a halogen atom or a C 1 -C 4 alkyl group;

then

R ³ is one of the following groups of formulas

It is a further object of the present invention to provide a process for the preparation of sulfonylaminocarbonyltriazolinones which comprises:

a) reacting the triazolinones of formula II

V344 / 94H in which

R ¹ and R ² are as defined above with a sulfonyl isocyanates of the formula III

R ³ - SO ₂ - N = C = O (III) in which

R ³ is as hereinbefore defined optionally in the presence of a solvent, or in the presence of a solvent

b) reacting the triazolinone derivatives of the general formula IV

in which

R ¹ and R ² are as defined above

Z is chlorine, C1-C4alkoxy, benzyloxy or phenoxy, with sulfonic acid amides of formula V

R ³ -SO ₂ -NH ₂ (V) wherein

R ³ is as defined above,

In 344/94 H optionally in the presence of an acid binding agent and optionally in the presence of a solvent, or in the presence of a solvent

c) reacting the triazolinones of formula II

in which

R ¹ and R ² have the meanings given above, with sulfonic acid amide derivatives of the general formula VI R ³ -SO ₂ -NH-CO -Z (II) (VI) in which

R ³ is as defined above and

Z is as defined above, optionally in the presence of an acid binding agent and optionally in the presence of a solvent, and optionally the compounds of formula (I) produced by process a), b) or c) are converted into their salts.

The novel sulfonylaminocarbonyltriazolinones of the formula I and their salts have a strong herbicidal activity. Surprisingly, the novel compounds of the formula I 'show a significantly better herbicidal action than the structurally similar known herbicide 1-isobutylaminocarbonyl-2-imidazolidinone (Isocarbamide).

Particularly preferred are the compounds of formula I ' ₍ wherein

R ¹ represents a hydrogen atom, optionally substituted by fluorine, chlorine, bromine, cyano, methoxy or ethoxy substituted

V344 / 94I1 alkyl of 1 to 4 carbon atoms, alkyl, cycloalkyl of 3 to 6 carbon atoms, phenyl, benzyl, alkoxy of 1 to 3 carbon atoms, alkylamino of 1 to 3 carbon atoms or dialkylamino of 1 to 3 carbon atoms 2 carbon atoms in the alkyl moieties,

R ² is hydrogen or fluorine and / or chlorine, methoxy or ethoxy-substituted alkyl having 1 to 4 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, phenyl, alkoxy of 1 to 3 carbon atoms, alkylamino of 1 to Or (C 1 -C 2) dialkylamino;

R ³ represents a group of the general formula

where

R ⁴ is fluoro, chloro, bromo, methyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy, 2-chloroethoxy, 2-methoxyethoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfinyl, carbon atoms, dimethylaminosulfonyl, diethylaminosulfonyl, N-methoxy-N-methylaminosulfonyl, phenyl, phenoxy or C 1 -C 3 alkoxycarbonyl; and

R ⁵ is hydrogen, fluoro, chloro or bromo;

then

R ³ represents a group of the general formula

V344 / 94H

K ¹⁰ where

R ¹⁰ is hydrogen,

R ¹¹ represents a fluorine atom, a chlorine atom, a bromine atom, a methyl group, a methoxy group, a difluoromethoxy group, a trifluoromethoxy group, an ethoxy group, a methoxycarbonyl group, an ethoxycarbonyl group, a methylsulfonyl group or a dimethylaminosulfonyl group;

R ¹² represents a hydrogen atom;

then

R ³ represents a group of the general formula

V344 / 94H

where

R is C 1 -C 4 alkyl, or is a group of formula

H

RO - (X \ _

R is C 1 -C 4 alkyl.

Table 1 below gives examples of compounds of the invention, cf. also exemplary embodiments.

V344 / 94H

Table 1

Examples of compounds of formula Ί R ¹

V344 / 94H

Table 1 - continued

R ²

O-CH ₂ -CH = CH ₂

COOC ₂ H ₅ ^C 2 ^H 5 C ₄ V ⁿ

CH 3 ^C 7 ^H

^C 3 ^H 7

CH ^C 2 ^H 5

V344 / 941-I

Table 1 - continued

R ¹ R ²

R ^{3 C} 2 ^H 5 oc ₂ h ₅

(CX) ₃ H ₇

Br /

I

CH3

Cl

V344 / 94H

Table 1 - continued

R ¹ R ² _ R ³

CH

COOCH ₃

N _{(CH3) 2}

λ //

CH ₂ ~

NH-CH ₃ CH ₃

V344 / 94H

Table 1 - continued

V344 / 94H

Table 1 - continued

R ¹ R ² __ R ³

ch ₃

CH

CH _Q 4 9

con (ch ₂ ) ₂

^C 3 ^H 7

V344 / 94H

Table 1 - continued

R ²

R ³

V344 / 94H

Table 1 - continued

R ¹ R ^{2 C} 2 = 5

ch ₃

V344 / 94H

Table 1 - continued

R ^z

R ³

V344 / 94H

Table 1 - continued

R ¹ R ² R ³

CH 2 O ₃

^C 2 ^H 5

V344 / I-94i

Table 1 - continued

R ¹ R ² _ R ³ oc ₂ h ₅ ^C 2 ^H 5

ch ₃ ch ₃

Br ₃ ^G 2 ^H 5

H3COOC /

\

N-CH

Cl

V344 / 94H

Table 1 - continued

R ^z ch ₃

CH ₃

CON _{(CH3) 2}

CH _{(CH3) 2}

H ₃ C

V344 / 94H

Table 1 - continued

R ¹ R ² R ³ ch ₃ ch (ch ₃ ) ₂

ch ₃ ch ₂ -o-ch ₃ ch ₃

V344 / 94H

Table 1 - continued

R ²

R ³

Br ch ₂ -ch = ch ₂ c ₂ h ₅

CH

V344 / I-94i

Table 1 - continued

R ¹ R ² R ^{3 C} 2 ^H 5

cooch ₃

COOC _n H _c

CH NHCH ₃ NHCH ₃ /

V344 / 94H

- »-»

Table 1 - continued

Si (CH _^7/3

V344 / 94H

Table 1 - continued

R ¹ R ² R ³

^C 2 ^H 5

N, ch ₃

^C 2 ^H 5

OCH ₃

CH _{(CH3) 2}

Table 1 - continued

CH c ₃ h ₇

V344 / 94II

Table 1 - continued

R ²

V344 / I-94i

Table 1 - continued

OCH ₂ CH ₂ -C 1

N _{(CH3) 2}

N _{(CH3) 2}

If, for example, 2,6-difluorophenyl isocyanate and 5-ethyl-4-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one are used as starting materials, the reaction according to the invention can be carried out according to the invention. variant a) is represented by the following reaction scheme:

F Q

If, for example, 2-methylthiobenzenesulfonic acid amide and 2-chlorocarbonyl-4-dimethylamino-2,4-dihydro-3H-1,2,4-triazol-3-one are used as starting materials, the reaction of the process according to the invention according to variant b) can be illustrated by the following reaction scheme:

V344 / 94H

SCH.

^SO 2 ^_NH 2

-HC1 ^>

If, for example, N-methoxycarbonyl-2-methoxybenzenesulfonamide and 5-diethylamino-4-difluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one are used as starting materials, the reaction according to the invention according to variant c can be carried out ) as shown in the following reaction scheme:

_OCH3 0 _{SO2 NH-COOCH3} +

CHF ₂ N (C ₂ H _{5) 2}

->

-HOCH ₃

The triazolinones used in processes of the invention according to variants a) and c) for the preparation of the compounds of formula I as starting materials are generally defined by formula II,

In the general formula symboly, the symbols R ¹ and R ² preferably have, in particular, the meanings already mentioned above in connection with the description of the compounds

V344 / 94H Formula J of the invention as preferred or as particularly preferred for the radicals R ¹ and R ^2nd

Table 2 below gives examples of starting materials of the general formula ΊΙ.

H 3 44/94 H

Table 2

Examples of starting materials of formula II

R ¹ R ² H H ch ₃ ^C 2 ^H 5 ^C 3 ^H 7 CH (CH ₃ ) ₂ ^C 4 ^H 9 CH ₂ CH (CH ₃ ) ₂ C (CH ₃ ) ₃ H H H H H H H H H H CH C C ^h 5 3 σ _Λ H CH _{(CH3) 2} H ^C A H ch ₂ ch (ch ₃ ) ₂ H C (CH ₃ > ₃ chf ₂ H ch ₂ ch ₂ cn H ch ₂ ch ₂ and ₃ H H cf ₃

V344 / 94H

Table 2

R ¹ R ² H ch ₂ and ₃ H ch ₂ oc ₂ h ₅ H ch ₂ ch ₂ and ₃ ch ₃ ch ₃ ch ₃ ^C 2 ^H 5 ch ₃ ^G 3 ^H 7 CH ₃ ch (ch ₃ ) ₂ CH ₃ C, H _q 4 9 CH ₃ ch ₂ ch (ch ₃ ) ₂ CH ₃ C _{(CH3) 3} ch ₃ ^C 3 ^H 7 ch ₃ CH _{(CH3) 2} ch ₃ CH _q 4 9 CH ₃ ch ₂ ch (ch ₃ ) ₂ CH ₃ ^C 2 ^H 5 c ₂ h ₅

V344 / I-94i

Table 2

R ¹ R ² C3H7 ° 3 ^H 6 CHF ₂ ^C 3 ^H 7 chf ₂ CH CHF ₂ ° 2 ^H 6 ch ₃ cf ₃ ^C 2 ^H 5 CF ₂ CF ₂ CH ₃ ^c 2 ^h 5 ^C 2 ^H 5 ° Λ ^C 6 ^H 5 CH ₃ CH ² _O-CH 1 \ _CH2 CH ₃ CH _O XI ^z CH ₃ -CH | A _C h ₂ CH ₃

V344 / I-94i

Table 2

R

R ²

X

CH ₃ ^C 2 ^H 5

CH n (ch ₃ ) ₂ n (ch ₃ ) ₂

^C 2 ^H 5 ^C 3 ^H 7

V344 / 94H

Table 2

R

R ²

V344 / 94H

Table 2

R ¹ R ² ch ₃ - \ ^H / nh ₂ CH ₃ ch ₃ NHCH ₃ NHCH ₃ ch ₃ NHCH ₃ ^C 2 ^H 5 NHCH ₃ ^C 3 ^H 7 N _{(CH3) 2} ch ₃ N _{(CH3) 2} 5 ', 2' N _{(CH3) 2} ^c 3 ^h ? OCH ₃ ch ₃ och ₃ ^C 2 ^H 5 OC ₂ H ₅ CH ₃ oc ₂ h ₅ ^C 2 ^H 5

V344 / 94H

Table 2

R

R ²

ch ₂ -oc ₂ h ₅

N _{(CH3) 2}

o-ch ₂ -ch = ch ₂ o-ch ₂ -ch = ch ₂

CH

C ₂ H

V344 / 94H

Table 2

R

R ² o-ch ₂ -ch = ch ₂ c ₃ h _?

O-CH ₉ -CH-CH ₉ -Br

I ^d Br och ₃

OCH ₃

V344 / 94H

Table 2

R

R ²

OCH.

CH ² V //

Ochna _{(CH3) 2}

O-CH ₂ -COOCH ₃

N (CH ₃ ) ₂ n (CH ₃ ) ₂

N _{(CH3) 2}

H oc ₂ h ₅

Ο ₃ Η7

344/94 H

Table 2

R

R ²

^C 2 ^H 5

_NH-CH3

CH ₃

CH ₂ -O-CH ₃

CH ₂ -O-CH ₃

CH ₂ -O-CH ₃

V344 / 94H

The starting materials of the formula II are known and / or can be prepared according to known processes (cf. Chem. Ber. 90 (1957), 909 921; ibid. 98 (1965), 3025-3099; J. Heterocycl. Chem. 15 ( 1978), 237-240, Tetrahedron 32 (1976), 2347-2352, Helv Chim Acta 63 (1980), 841-859, J. Chem Soc, C 1967, 746-751, EP-A 283876; -A 294666; EP-A 301946; EPA 298371; DE-P 3839206 / LeA 26538 of November 19, 1988; DE-P 3916207 / LeA 26849 of 18.05.1989; DE-P 3916208 / LeA 26850 of May 18, 1988; 1989; J. Chem. Soc., 1970, 26-34; DE-P 3916930 / LeA 26886 of 24/05/1989).

The triazolinones of the formula II can be obtained, for example, by (a) reacting the oxadiazolinones of the formula VII

in which

R ² is as defined above, the amino derivatives of formula VIIIa

H ₂ NR ¹ (VIII) in which

R ¹ is as defined above, optionally in the presence of a solvent such as water at temperatures between 20 ° C and 120 ° C, and the hydrazine derivatives of the general formula IX 'thus formed

H CO-NH-R ¹ /

N

I (IX),

N

Z \ 2

H CO — R in which

344/94 H

R ¹ and R ² have the meanings given above, are isolated according to conventional methods (cf. examples) and - or optionally also without intermediate isolation - the compounds of the general formula J 1 are condensed, optionally in the presence of a basic condensation auxiliary such as sodium hydroxide and optionally in the presence of a solvent, such as water, at temperatures between 20 ° C and 120 ° C to give compounds of formula II (cf. EP-A 301946, DE-OS 3743493 / LeA 25759 and examples), or

(b) amino derivatives of formula (VIII)

H ₂ NR ¹ (VIII) in which

R ¹ is as defined above, are reacted with carbonic acid derivatives, such as, for example, diphenyl carbonate, then with hydrazine or hydrazine hydrate and eventually with a carboxylic acid derivative or carbonic acid of formula X (RO) ₃ CR ² (X), wherein

R ² is as defined above, and

R represents a lower alkyl group, optionally in the presence of a solvent such as ethylene chloride, at temperatures between 0 ° C and 150 ° C (cf. DE-P 3 920 270 (LeA 26937 of 21.06.1989, DE-P3 928 662)) LeA 27137 of Aug. 30, 1989 and Examples).

The present invention also relates to novel triazolinones of formula IIa

V344 / 94H

Ο

in which

A ¹ is in each case an optionally substituted alkyl, alkenyl, cycloalkyl, alkoxy or dialkylamino group and

A ² represents a hydrogen atom or an optionally substituted alkyl group, a cycloalkyl group, an aralkyl group, an aryl group or an alkoxy group, provided that A ¹ and A ^{2 are} not both alkyl simultaneously.

The novel triazolinones of the formula IIIa 'are obtained, for example, by either oxadiazolinones of the formula VIIa

H-Ni

N

(Villa) ^X A in which

A ² are as defined above, reacted with amino derivatives of formula VIIa

H ₂ NA ¹ (VIIIa) in which

A ¹ has the meaning given above, analogously to the procedure described above ad oQ, or amino derivatives of the general formula IIIa '

V344 / 94H

Η ₂ Ν-Α ¹ (VIIIa) in which

A ¹ is as defined above, are reacted with carbonic acid derivatives and then with hydrazine or hydrazine hydrate and eventually with a carboxylic acid derivative or with a derivative of carbonic acid of formula Xa (RO) ₃ CA ² (Xa), wherein

A ² and R have the meanings given above, analogously to the procedure described above in ad β) (cf. the examples below).

In the general formula, IIIa means

Preferably, A ¹ is C 1 -C 6 alkyl, C 3 -C 5 alkenyl, C 3 -C 6 cycloalkyl, optionally fluorine, chlorine, bromine, cyano, C 1 -C 4 alkoxy or C 1 -C 4 alkoxycarbonyl C 1 -C 4 alkoxy substituted by C 1 -C 6 alkoxy, in particular methyl, ethyl, allyl, cyclopropyl, methoxy, ethoxy, propoxy or isopropoxy, or C 1 -C 4 dialkylamino, especially dimethylamino or diethylamino; and

A @ ² is preferably hydrogen, optionally fluorine, chlorine, bromine, cyano, (C1 -C4) alkoxy, (C1 -C4) alkylcarbonyl or (C1 -C4) alkoxycarbonyl substituted alkyl; C 1 -C 6; optionally substituted (C 1 -C 4) cycloalkyl substituted with fluoro, chloro, bromo and / or C 1 -C 4 alkyl

V344 / 94H carbon atoms; optionally fluorine, chlorine, bromine, cyano, nitro, C 1 -C 4 alkyl, trifluoromethyl, C 1 -C 4 alkoxy and / or C 1 -C 4 alkoxycarbonyl substituted by C 1 -C 4 alkoxy 3 carbon atoms in the alkyl moiety; optionally fluorine, chlorine, bromine, cyano, nitro, C 1 -C 4 alkyl, trifluoromethyl, C 1 -C 4 alkoxy, fluorine and / or chlorine C 1 -C 4 alkoxy, C 1 -C 4 alkylthio C 1 -C 3 alkylthio, C 1 -C 3 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl or C 1 -C 4 alkoxycarbonyl substituted in the alkoxy moiety substituted by phenyl or is C1-C4alkoxy, in particular hydrogen, optionally fluorine and / or chlorine, methoxy or ethoxy substituted alkyl of 1 to 4 carbon atoms, methoxy, ethoxy or cycloalkyl of 3 to 6 carbon atoms, including that A ¹ and A ^{2 are} not both alkyl groups simultaneously.

Compounds of formulas VII, VIIa, VIIa, VIIIa and Xa and Xa, respectively, which are used as starting materials in the preparation of the triazolinones of formulas IIa and IIIa are known compounds (cf. Helv. Chim. Acta 55 (1972)). 1174; EP-A 301946; DE-OS 3743493).

The sulfonyl isocyanates which are used as further starting materials in the process of variant a) for the preparation of the compounds of the general formula (I) are generally defined by the formula (II ').

In the general formula (III), the symbol R ³ preferably or particularly preferably has the meaning already mentioned in connection with the description of the compounds of the formula I 'according to the invention as advantageous or particularly preferred for the symbol

V344 / 94H

Examples of starting materials of formula III 'include:

2-fluoro-, 2-chloro-, 2-bromo-, 2-methyl-, 2-methoxy-, 2-trifluoromethyl-, 2-difluoromethoxy, 2-trifluoromethoxy-, 2-methylthio-, 2-ethylthio-, 2 -propylthio-, 2-methylsulfinyl-, 2-methylsulfonyl-, 2-dimethylaminosulfonyl-, 2-diethylaminosulfonyl-, 2- (N-methoxy-N-methyl) -aminosulfonyl-, 2-phenyl-, 2-phenoxy-, 2-methoxycarbonyl-, 2-ethoxycarbonyl-, 2-propoxycarbonyl- and 2-isopropoxycarbonylphenylsulphonylisocyanate, 2-fluoro-, 2-chloro-, 2-difluoromethoxy-, 2-trifluoromethoxy-, 2-methoxycarbonyl- and 2-ethoxycarbonylbenzylsulphonyl- isocyanate, 2-methoxy- - and 4-ethoxycarbonyl-1-methylpyrazol-5-ylsulfonyl isocyanate.

The sulfonyl isocyanates of the formula III 'are known and / or can be prepared according to known processes (cf. U.S. Patent Nos. 4,1 127,405, 4,169,719, 4,371,391; EP-A 7,687, 13,480, 21,641, 23,141, 23,422, 30,139, 35,893, 44,808, 44,809, 48,143, 51,466, 64,322, 70,041, 173,312).

The process according to the invention according to variant a) for the preparation of the novel compounds of the general formula J 'is carried out preferably using solvents. Practically all inert organic solvents are suitable as solvents. These preferably include aliphatic and aromatic or halogenated hydrocarbons such as pentane, hexane, heptane, cyclohexane, petroleum ether, gasoline, ligroin, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, ethers, diethyl ether and dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxane, ketones such as acetone, methyl ethyl ketone, methyl isopropyl ketone and methyl isobutyl ketone, esters such as acetic acid methyl ester and ethyl acetate, nitriles such as acetonitrile and formamide N-methylpyrrolidone as well as dimethylsulfoxide, tetramethylenesulfone and hexamethylphosphoric triamide.

In the process according to variant a), the reaction temperatures can be varied to a considerable extent. In general, the reaction is carried out at temperatures between 0 ° C and 150 ° C, preferably at temperatures between 10 ° C and 80 ° C.

V344 / 94H

The process according to the invention according to variant a) is generally carried out at atmospheric pressure.

In carrying out the process according to the invention according to variant a), a sulfonyl isocyanate of the formula III is used per 1 mol of triazolinone of the formula II, in general between 1 and 3 mol, preferably between 1 and 2 mol

The reactants may be contacted with each other in any order. The reaction mixture is stirred until the reaction is complete, concentrated and the crude product contained in the residue is crystallized with a suitable solvent such as diethyl ether. Product of formula Ί; The crystals formed are isolated by filtration.

The triazolinone derivatives which are used as starting materials in the process according to the invention according to variant b) are generally defined by the formula IV;

In formula IV, R ¹ and R ² preferably or particularly preferably have the meanings already given in connection with the description of the compounds of formula J 'according to the invention as being preferred or particularly preferred for R ¹ and R ² and

Z is preferably chlorine, C1-C4alkoxy, benzyloxy or phenoxy, in particular methoxy or phenoxy.

Possible examples of starting materials of formula IV are compounds of formula IV ', which can be prepared from compounds of formula j1 shown in Table 2, and from phosgene, chloroformic acid methyl ester, chloroformic acid benzyl ester, chloroformic acid phenyl ester or diphenyl carbonate.

The starting materials of the formula IV 'are known and / or can be prepared according to known processes (cf. EP-A 283876; EP-A 294666; EP-A 298371).

Thus, triazolinone derivatives of the formula V are obtained, for example, by reacting triazolinones of the formula III '.

V344 / 94H II

R ¹ and R ² are as defined above, with carbonic acid derivatives of the general formula XI Z-CO-Z ¹ (XI) in which:

Z has the meaning given above and

Z ¹ is a leaving group such as chlorine, methoxy, benzyloxy or phenoxy, optionally in the presence of a solvent such as tetrahydrofuran and optionally in the presence of an acid binding agent such as sodium hydride or potassium tert-butoxide at temperatures between -20 ° C and + 100 ° C (cf. examples).

The sulfonic acid amides which are used as further starting materials in the process according to the invention according to variant b) for the production of compounds of the formula I are generally defined by the formula V.

In formula V ', R ³ preferably or particularly preferably has the same meaning as previously described in relation to the compounds of formula J; of the invention as preferred or as particularly preferred for R symbol ^third

Examples of starting compounds of formula V include:

2-fluoro-, 2-chloro-, 2-bromo-, 2-methyl-, 2-methoxy-, 2-trifluoromethyl-, 2-difluoromethoxy-, 2-trifluoromethoxy-, 2-methylthio-, 2-ethylthio-, 2-propylthio-, 2-methylsulfonyl-, 2-methylsulfinyl-, 2-dimethylaminosulfonyl-, 2-diethylaminosulfonyl-, 2- (N-methoxy-N-methyl) aminosulfonyl-, 2-phenyl-, 2-phenoxy-, 2-methoxycarbonyl-, 2-ethoxycarbonyl-, 2-propoxycarbonyl- and 2-isopropoxycarbonylbenzenesulfonamide, 2-fluoro-, 2144/94H chloro-, 2-difluoromethoxy-, 2-trifluoromethoxy-, 2-methoxycarbonyl- and 2-ethoxycarbonylphenylmethanesulfonamide, 2-methoxy- 4-methoxycarbonyl- and 4-ethoxycarbonyl-1-methylpyrazole-5-sulfonamide.

The sulfonic acid amides of the formula V 'are known and / or can be prepared by known processes (cf. U.S. Patent Nos. 4,127,405, 4,169,719, 4,371,391; EP-A 7 687, 13 480, 21 641, 23 141 , 23,422, 30,139, 35,893, 44,808, 44,809, 48,143, 51,466, 64,322, 70,041, 173,312).

The process according to the invention according to variant b) for the preparation of the compounds of the formula I is preferably carried out using solvents. Suitable solvents here are virtually all inert organic solvents, such as those mentioned above for process variant a).

In the process of variant b), all acid binding agents usually used for such types of reactions can be used as acid binding agents. Preferred are alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkaline earth metal hydroxides such as calcium hydroxide, alkali metal carbonates and alkoxides such as sodium carbonate and potassium carbonate, sodium tert-butoxide and potassium tert-butoxide; aliphatic, aromatic or heterocyclic amines such as triethylamine, trimethylamine, dimethylaniline, dimethylbenzylamine, pyridine, 1,5-diazabicyclo [4.3.0] n-5-ene (DBN), 1,8-diazabicyclo [5,4,0] undec -7-ene (DBU) and 1,4-diazabicyclo [2.2.2] octane (DABCO).

In the process according to variant b), the reaction temperatures can be varied within a wide range. In general, the reaction is carried out at temperatures between 0 ° C and 100 ° C, preferably at temperatures between 10 ° C and 60 ° C.

The process according to the invention according to variant b) is carried out at atmospheric pressure. However, it is also possible to work at elevated or reduced pressure.

In carrying out the process according to the invention according to variant b), the required starting materials are always used in general in approximately equimolar amounts. However, it is also possible to use one of the two always used

V344 / 94H components in larger excess. The reactions are generally carried out in a suitable solvent in the presence of an acid binding agent and the reaction mixture is stirred for several hours at the desired temperature. The processing is carried out in accordance with process variant b) according to the usual methods.

The triazolinones of formula II which are used as starting materials in the preparation of the compounds of formula T according to variant c) of the process according to the invention have already been described as starting materials for variant a) of the process according to the invention.

The sulfonic acid amide derivatives which are used as further starting materials in the preparation of the compounds of formula T according to variant c) of the process according to the invention are generally defined by formula VIj.

In formula VI t, the symbols R ³ and Z preferably, and in particular, have the meanings already mentioned in connection with the description of the compounds of the formula Ί according to the invention or the description of the compounds of the formula IV as preferred or particularly preferred for the symbols R ³ and Z.

Process variant c) is preferably carried out using solvents. The same organic solvents mentioned in connection with the description of the process according to the invention according to variant a) are suitable.

Optionally, the process of variant c) is carried out in the presence of an acid binding agent. The same acid-binding agents mentioned in connection with the description of the process according to the invention according to variant b) are suitable.

The reaction temperatures in process c) according to the invention can be varied to a considerable extent. In general, the reaction is carried out at temperatures between 0 ° C and 100 ° C, preferably at temperatures between 10 ° C and 60 ° C.

Process (c) according to the invention is generally carried out at atmospheric pressure. However, it is also possible to work at elevated or reduced pressure.

In carrying out the process according to the invention according to variant c), the starting materials required are generally used in approximately equimolar amounts. However, it is also possible to use one of the two reactants in the

V344 / 94H larger excess. The reactions are generally carried out in a suitable solvent in the presence of an acid binding agent and the reaction mixture is stirred for several hours at the desired temperature. The processing is carried out in accordance with process variant c) according to the usual methods.

For conversion to salts, the compounds of formula J 'are mixed with suitable salt formers, such as sodium or potassium hydroxide, sodium or potassium methoxide or ethoxide, ammonia, isopropylamine, dibutylamine or triethylamine, in suitable solvents such as water, methanol or ethanol. The salts may be isolated, optionally after concentration, in the form of crystalline products.

The active compounds according to the invention can be used as defoliating agents, desiccants, weed control agents and in particular as weed control agents. Weeds, in the broadest sense, mean all plants that grow where they are undesirable. Whether the compounds of the invention act as total or selective herbicides depends essentially on the amount used.

The active compounds according to the invention can be used, for example, in the following plants: dioecious weeds of the genera:

mustard (Sinapis), cress (Lepidium), rhododendron (Gallium), starfish (Stellaria), camomile (Matricaria), ruman (Anthemis), galingsoga (Galinsoga), carrot (Chenopodium), rhizome (Urtica), ragwort (Senecio), Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus Milk (Sonchus), Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Durman (Datura), Violet (Viola), Galeopsis , poppy (Papaver), neva (Centaurea), clover (Trifolium), Ranunculus, Taraxacum; dicotyledonous plants of the genera:

V344 / 94H cotton (Gossypius), soy (Glycine), beets (Beta), carrots (Daucus), beans (Phaseolus), peas (Pisum), potatoes (Solanum), flax (Linum), teat (Ipomoea), vetch ( Vicia), tobacco (Nicotiana), tomato (Lycopersicon), peanut (Arachis), kohlrabi (Brassica), lettuce (Lactuca), cucumber (Cucumis), pumpkin (Cucurbita);

monoecious weeds of genera:

hedgehog (Echinochlora), bar (Setaria), millet (Panicum), fingergrass (Digitaria), timothy (Phleum), grayling (Poa), fescue (Festuca), eleusine (Eleusine), Brachiaria, Buttercup (Lolium), Barn (Bromus) ), oats (Avena), chess (Cyperus), sorghum (Sorghum), wheatgrass (Agropyron), wreckage (Cynodon), Monochoria, Fimbristylis, rosehip (Sagittaria), Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium Agrostis), psiarka (Alopecurus), whisk (Apera);

monoecious cultural plants:

rice (Oryza), maize (Zea), wheat (Triticum), barley (Hordeum), oats (Avena), rye (Secale), sorghum (Sorghum), millet (Panicum), sugar cane (Saccharum), pineapple (Pineapple) , Asparagus (Asparagus), Garlic (Allium).

However, the use of the active compounds according to the invention is in no way limited to these genera, but applies equally to other plants.

The compounds according to the invention are suitable, depending on the concentration, for the total eradication of weeds, for example on industrial and railway surfaces and on roads and squares, possibly with trees. The compounds of the invention may also be used for weed control in long-term crops such as forest crops, ornamental trees, fruit trees, vineyards, citrus, nut, banana, coffee, tea, rubber, coconut, cocoa, cocoa, berry and hop plants, ornamental and sports lawns and pastures, and selective weed control in annual crops.

V344 / 94H

The compounds of formula (I ') according to the invention are suitable for controlling monocotyledonous and dicotyledonous weeds, both in pre-emergence and post-emergence treatments. These compounds are significantly more potent than, for example, Isocarbamide.

To a certain extent, the compounds according to the invention also exhibit fungicidal activity, for example against powdery mildew fungi and against apple scabs and against Pyricularia oryzae on rice.

The active substances can be converted into the customary formulations such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granulates, concentrates based on suspensions and emulsions, natural and synthetic substances impregnated with active substances and small particles coated with polymeric substances. substances.

These compositions are prepared in a known manner, for example by mixing the active ingredient with fillers, i.e. liquid solvents and / or solid carriers, optionally using surfactants, i.e. emulsifiers and / or dispersants and / or foaming agents. If water is used as a filler, it is also possible to use, for example, organic solvents as co-solvents.

In principle, suitable liquid solvents are:

aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, alcohols such as butanol or glycol, as well as their ethers and esters ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethylsulfoxide, as well as water.

Suitable solid carriers are:

natural stone meal, such as kaolins, alumina, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth; and synthetic stone meal, such as highly disperse silica, alumina and silicates. Suitable solid carriers for the preparation of granules are crushed and fractionated natural stone materials such as limestone, marble, pumice,

V344 / 94H sepiolite and dolomite, as well as synthetic granules of inorganic and organic flours and granules of organic material, as well as sawdust, coconut shell, corn sticks and tobacco stems. Suitable emulsifiers and / or foaming agents are non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, fatty alcohol polyoxyethylene ethers, e.g.

The compositions of the invention may include adhesives such as carboxymethylcellulose, natural and synthetic powdered, granular or latex polymers such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids such as cephalin and lecithin and synthetic phospholipids. Other additives may be mineral and vegetable oils.

Furthermore, the compositions may contain coloring agents such as inorganic pigments, for example iron oxide, titanium dioxide and ferrocyanide blue, and organic dyes such as alizarin dyes, azo dyes and metallic phthalocyanine dyes, as well as trace nutrients such as iron, manganese, boron, copper salts. , cobalt, molybdenum and zinc.

The compositions generally contain between 0.1 and 95% by weight of active ingredient, preferably between 0.5 and 90% by weight of active ingredient.

The active compounds according to the invention can also be used in mixtures with known herbicides in the control of weeds as such or in the corresponding compositions, and final mixing prior to application (tankmix) is also possible as finished compositions.

Known herbicides, such as, for example, are suitable for these mixtures

1-amino-6-ethylthio-3- (2,2-dimethylpropyl) -1,3,5-triazine-2,4- (1H, 3H) -dione (AMETHYDIONE), or

N- (2-benzothiazolyl) -N, N'-dimethylurea (METABENZTHIAZURON) for weed control in cereals;

V344 / 94H

4-amino-3-methyl-6-phenyl-1,2,4-triazin-5 (4H) -one (METAMITRON) for weed control in sugar beet and

4-amino-6- (1,1-dimethylethyl) -3-methylthio-1,2,4-triazin-5 (4H) -one (METRIBUZIN) for soybean weed control;

they are also possible

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-trifluoromethylphenoxy) -2-nitrobenzoic acid (ACIFLUORFEN), N- (methoxymethyl) -2,6-diethylanilide chloroacetic acid (ALACHLOR),

2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine (ATRAZIN), 2 - [[[[[[[(4,6-dimethoxypyrimidin-2-yl) amino] carbonyl] amino] sulfonyl methyl ester ] methylbenzoic acid (BENSULFURON)

3-isopropyl-2,1,3-benzothiadiazin-4-one 2,2-dioxide (BENTAZON), methyl 5- (2,4-dichlorophenoxy) -2-nitrobenzoate (BIFENOX),

3,5-dibromo-4-hydroxybenzonitrile (BROMOXYNIL),

N- (butoxymethyl) -2-chloro-N- (2,6-diethylphenyl) acetamide (BUTACHLOR), ethyl 2 - {[(4-chloro-6-methoxy-2-pyrimidinyl) aminocarbonyl] aminosulfonyl} benzoate (CHLORIMURON) )

2-chloro-N - {[(4-methoxy-6-methyl-1,3,5-triazin-2-yl) amino] carabonyl} benzenesulfonamide (CHLORSULFURON),

N, N-dimethyl-N '- (3-chloro-4-methylphenyl) urea (CHLORTOLURON), 2-chloro-4-ethylamino-6- (3-cyanopropylamino) -1,3,5-triazine (CYANAZIN),

2,6-dichlorobenzonitrile (DICLOBENIL),

2- [4- (2,4-Dichlorophenoxy) phenoxy] propionic acid, its methyl ester or its ethyl ester (DICLOFOP),

V344 / 94H

2 - [(2-chlorophenyl) methyl] -4,4-dimethylisoxazolidin-3-one (DIMETHAZONE),

4-amino-6-tert-butyl-3-ethylthio-1,2,4-triazin-5 (4H) -one (ETHIOZIN),

2- {4 - [(6-chloro-2-benzoxazolyl) oxy] phenoxy} propanoic acid, its methyl ester or its ethyl ester (FENOXAPROP),

2- [4- (5-Trifluoromethyl-2-pyridyloxy) phenoxy] propanoic acid or its butyl ester (FLUAZIFOP),

N, N-dimethyl-N '- (3-trifluoromethylphenyl) urea (FLUOMETURON),

1-Methyl-3-phenyl-5- (3-trifluoromethylphenyl) -4-pyridone (FLURIDONE)

5- (2-chloro-4-trifluoromethylphenoxy) -N-methylsulfonyl-2-nitrobenzamide (FOMESAFEN),

N-phosphonomethylglycine (GLAPHOSATE), methyl 2- [4,5-dihydro-4-methyl-4- (1-methylethyl) -5-oxo-1H-imidazol-2-yl] -4 (5) methylbenzoate (IMAZAMETHABENZ) )

2- (4,5-Dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl) pyridine-3-carboxylic acid (IMAZAPYR),

2- [5-methyl-5- (1-methylethyl) -4-oxo-2-imidazolin-2-yl] -3-quinolinecarboxylic acid (IMAZAQUIN),

2- [4,5-dihydro-4-methyl-4-isopropyl-5-oxo- (1 H) imidazol-2-yl] -5-ethylpyridine-3-carboxylic acid (IMAZETHAPYR),

3,5-diiodo-4-hydroxybenzonitrile (IOXYNIL), N, N-dimethyl-N '- (4-isopropylphenyl) urea (ISOPROTURONE), (2-methyl-4-chlorophenoxy) acetic acid (MCPA), (4- chloro-2-methylphenoxy) propionic acid (MCPP),

N-methyl-2- (1,3-benzothiazol-2-yloxy) acetanilide (MEFENACET),

2-chloro-N- (2,6-dimethylphenyl) -N - [(1H) pyrazol-1-ylmethyl] acetamide (METAZACHLOR),

2-ethyl-6-methyl-N- (1-methyl-2-methoxyethyl) chloroacetanilide (METOLACHLOR),

V344 / 94H

2 - {[[((4-methoxy-6-methyl-1,3,5-triazin-2-yl) amino) carbonyl] amino] sulfonyl] benzoic acid or its methyl ester (METSULFURON),

1- (3-Trifluoromethylphenyl) -4-methylamino-5-chloro-6-pyridazone (NORFLURAZON)

N- (1-ethylpropyl) -3,4-dimethyl-2,6-dinitroaniline (PENDIMETHALIN),

O- (6-chloro-3-phenylpyridazin-4-yl) -S-octylthiocarbamate (PYRIDATE), 2- [4- (6-chloro-quinoxalin-2-yloxy) -phenoxy] -propionic acid ethyl ester (QUIZALOFOPETHYL),

2- [1- (etoxamino) butylidene] -5- (2-ethylthiopropyl-1,3-cyclohexadione (SETOXYDIM), methyl 2 - {[4,6-dimethyl-2-pyrimidinyl) aminocarbonyl] aminosulfonyl} benzoate (SULFOMETURON) )

4-ethylamino-2-tert-butylamino-6-methylthio-sec-triazine (TERBUTRYNE), 3 - [[[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl) amino] methyl ester ] carbonyl] amino] sulfonyl] thiophene-2-carboxylic acid (THIAMETURON), N, N-diisopropyl-S- (2,3,3-trichloralyl) thiolcarbamate (TRIALLATE),

2,6-dinitro-4-trifluoromethyl-N, N-dipropylaniline (TRIFLURALIN).

Surprisingly, some compositions also exhibit a synergistic effect.

Mixing with other known active ingredients such as fungicides, insecticides, acaricides, nematicides, avian protective agents, plant nutrients and soil conditioners is also possible.

The active ingredients may be administered as such, in the form of concentrates or dosage forms prepared therefrom, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. The application is carried out in a conventional manner, for example by watering, spraying, sprinkling or dusting.

The active compounds according to the invention can be applied both before and after the emergence of the plants.

The active compounds according to the invention can also be incorporated into the soil before sowing.

V344 / 94H

The amount of active ingredient to be administered can vary widely. This amount depends essentially on the type of effect desired. In general, the application rate is between 0.01 and 15 kg of active ingredient per hectare of soil area, preferably from 0.05 to 10 kg of active ingredient per hectare.

The production and use of the active compounds according to the invention are described in more detail in the following examples. However, these examples do not limit the scope of the invention in any way.

V344 / 94H

DETAILED DESCRIPTION OF THE INVENTION

Example 1

(Procedure (a))

3.0 g (17.95 mmol) of 4-cyclopentyl-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one are dissolved in 60 ml of acetonitrile and 6 ml of acetonitrile are added thereto under stirring. 9 g (28.6 mmol) of 2-methoxycarbonylphenylsulfonyl isocyanate dissolved in 20 ml of acetonitrile. The reaction mixture was stirred at 20 ° C for 6 hours and then evaporated. The remaining residue is stirred with diethyl ether and the product obtained in the form of crystals is collected by suction filtration.

6.6 g (90% of theory) of 4-cyclopentyl-5-methyl-2- (2-methoxycarbonylphenylsulfonylaminocarbonyl) -2,4-dihydro-3H-1,2,4-triazol-3-one are obtained. .

Example 2

Cl

(Procedure b))

1.8 g (11.8 mmol) of 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU) is added to a mixture of 3.0 g (12.1 mmol) of 5-ethyl- 4-methyl-2-phenoxycarbonyl-2,4V344 / 94H dihydro-3H-1,2,4-triazol-3-one, 2.5 g (12.2 mmol) of 2-chloro-6-methylbenzenesulfonamide and 60 ml of acetonitrile. The reaction mixture is stirred at 20 ° C for 2 hours, then poured into approximately twice the volume of ice water and the pH is adjusted to approximately 2 by dropwise addition of concentrated hydrochloric acid. The product which precipitates in crystalline form is isolated by filtration.

3.2 g (73.5% of theory) of 5-ethyl-4-methyl-2- (2-chloro-6-methylphenylsulfonylaminocarbonyl) -2,4-dihydro-3H-1,2,4-triazol-3-one are obtained. melting point 176 ° C.

Analogously to Examples 1 and 2 as well as in accordance with the general description of the processes of the invention, the compounds shown in Table 3 below may also be prepared:

(I)

V344 / 94H

Table 3

Examples of prepared compounds of formula I

Example # R ¹ _R ² _R ^ _Teplota point (° C) _COOCH3 ^C 6 ^H 5 ^CH 3

158

0CHF _o / ²

CH ₃ C ₂ H ₅

159

C ₂ H ₅ C ₂ H ₅

CH ₃ C ₃ H ₇

115

143

V344 / 94II

Table 3 - continued

Example # R ¹ _fť_β! _ Melting point (° C)

io och ₃

180

V344 / 94H

Table 3 - continued

Example ¹ _R ^ č._R _β! _Teplota point (° C) ii _{OCH3 CH3}

OCH ₃ C ₂ H ₅

OCH ₃ C ₃ H _?

128

CH ₃ C ₂ H ₅

173

344 / 941-1

Table 3 - continued

Example # R ^{1 -} R ²

R ³ _ Melting point (° C) with ₂ n (ch ₃ ) ₂ /

CH ₃ ^C 3 ^H 7 λ / z

133

^C 2 ^H 5

_OCH3 CH _{(CH3) 2}

154

137

174

V344 / 94 H

Table 3 - continued

Example # R @ 1 R @ 4 _ Melting point (° C)

168

174

136 \

CH

V344 / 94H

Table 3 - continued

Example # R ¹ _BÍ_B1 - Melting point (° C)

N (CH ₃ ) ₂ C ₂ H ₅

139

N (CH ₃ ) ₂ H

197

N (CH ₃ ) ₂ CH (CH ₃ ) ₂

OC ₂ H ₅ ^C 2 ^H 5 Cooch ₃ Cooch ₃

148

153

V344 / 94H

Table 3 - continued

Example No._R? _Β! _Β! _ Melting point (° C)

COOCH27 OC ₂ H ₅ //

155

COOCH

CH _{(CH3) 2} /

186

146

110

V344 / 94H

Table 3 - continued

Example # R ¹ _R ^ _β! _Teplota point (° C) N _{(CH3) 2}

^C 4 ^ 9

131

CH ₃ \\ //

C ₃ H _? ^C 4 ^H 9 cooch ₂

113

COOCH-, / ³

V344 / 94I1

Table 3 - continued

COOCH ₃

OCH ₃ //

117

COOCH

CH ₃

λ //

141

C ₂ H ₅

130

V344 / 94H

Table 3 - continued

Example # _Rj_R ^ _R ^ _ Melting point (° C)

COOCH ^ ^C 3 ^H 7

//

139

COOCH

λ //

151

CH (CH _{3) 2} NHCH (CH _{3) 2}

151

135

V344 / 94H

Table 3 - continued

COOCH ₃

C ₂ H ₅

N (CH ₃ ) ₂

134

CH,

2 5

167

V344 / 94H

Table 3 - continued

Example No. _R ¹ _R ² _R ^ _ Melting point (° C)

120

120

-CH ₂ CH = CH ₂ C ₂ H ₅

V344 / 94H

Table 3 - continued

Example No._Ŕj_R ^ _R ^ _ Melting point (° C)

.V344 / 94H

Table 3 - continued

Example # R ¹ R ²

R ³

Melting point f

^C 3 ^H 7

103

^C 2 ^H 5

127

OCH ₃ C ₂ H ₅

V344 / I-94i

Table 3 - continued

EXAMPLE # R ¹ _ R 1 _ R ¹ _; _ Melting point (° C)

OCF.

-NHCH ^ C ^ H ^ -n //

196

CH ₃ Ο ^ Ηγ-η

178

177

123

-CH ₂ -CH = CH ₂ ^C 3 ^H 7 ^_N

(ammonium product)

V344 / 94H

Table 3 - continued

Example #_Rj_R? _BZ_Temperature (° C)

117

182

133

V344 / 94H

Table 3 - continued

Example # R ¹ __β! _Β! _ Melting point (° C)

162

-CH ₂ -CH = CH ₂ CH ₃

120

COOCH-, / ³

V344 / 94H

Table 3 - continued

COOCH.

CK (CH _{3) 2}

191

COOCH /

191

V344 / I-94i

Table 3 - continued

Example č._Rj_R _R ^ ^ _Teplota point (° C) _COOCH3

192

-C (CH ₃ ) ₃ H

COOCH

211

-CH-CH-CH 3 T CH

I

br

110

CH ₃ -CH ₂ OCH ₃

CH ₃ C ₂ H ₅ cooch ₃

152

174

3 44 / 94II

Table 3 - continued

Example No, _Rj_R ^ _R ^ _ Melting point (° C)

CH ₃ -CH ₂ OC ₂ H ₅

-OCH ₃ C ₃ H _? -n

123 (amorphous product)

^C 2 ^H 5

-ch ₂ and ₃

102

V344 / 94H

Table 3 - continued R ¹ R ²

R ³

Melting point (° C) ch ₂ and ₃ ch ₂ oc ₂ h ₅ ch ₂ oc ₂ h ₅

155

123

Cl

N (CH

189

CH

V344 / 94H

Table 3 - continued

-OCH ₃ C 1 H -n

V 34 4 / 941-1

Table 3 - continued

Example #

R ¹

R ²

R ³

Melting point (° C)

-oc ₂ h ₅ ^C 2 ^H 5

-oc ₂ h ₅

// \\

132

107

-och ₃

CH _{(CH3) 2}

128

V344 / I-94i

Table 3 - continued

Example No. R ¹ 1 R ³ _ R ³ _ Melting point (° C)

C ^ H ^ n

100

140

-N _{(CH3) 2}

-N _{(CH3) 2 COOCH3}

163

182

V344 / 9411

Table 3 - continued

Example # _Ft_β! _Β! _ Melting point (° C)

V344 / I-94i

Table 3 - continued

Example No. _R ¹ _B ¹ _B ¹ _ Melting point (° C)

105 -CH ₂ -CH = CH ₂

106 -CH ₂ -CH = CH ₂

107 OC ₂ H ₅

108 -OC ₂ H ₅

109

104

147

136

V344 / 94i-1

Table 3 - continued

Example # _R ¹ _Rf_Rf_Temperature (° C)

109 -0CH ₃ CH (CH ₃ ) ₂ no ch ₃ ch ₃

126

146

111

U2 CH ₃ CH (CH _{3) 2}

CH

175

124

V344 / 94H

Table 3 - continued

Example No. _R ¹ _R ¹ _R ¹ _ Melting point (° C)

Cl

113

171

Cl

V344 / 94II

Table 3 - continued

Example # _R? _R ^ _R ³ _ Melting point (° C)

V344 / 94H continued

R ¹ R ² R ³

Melting point (° C)

Table 3

Example #

121

122

123

p.i.

125

126

127

18

172

122 amo y

164

172

V344 / 94H

100

Table 3 - continued

Example No, ¹ _R _R ^ __ Melting point (° C) C

V344 / 94H

101

Table 3

Example #

continued R ¹ R ²

R_Temperature ( ^g C)

L 3 6

137

L 38

L 3 9

140

L 4 L

142

143 ch (ch ₃ ) ₂ c ₂ h ₅

C 1 <CCH · ch (ch ₃ ) ₂

125

Cjŕíyn CH (CH ₃₎ C n (CK _{3) 2} C 3 C _{3 3? 7} -n CH ₃ ^{C 3? 7 n C} 2 ^H 5 CH (CH _{3) 2} C ₂ H ₅

ex

COOCH _Ί

COOCHcy

COOCHcy

250

255

165

130

187

133

V344 / 94II

1 () 2

Table 3

Example #

- continuation

R ¹

R ^z

R ³ _ Melting point (° C)

COOCHcc

225

1 & 5 i Λ5 li 7

K3

1AQ

150 i 5l ^C 2 ^H 5 ^C 3 ^H 7 ' ^r ·

CH-, CH (CH-,)

COOCHCOOCH ·

CCOCH-, ^J

COOCH ₂ CH 2 CH ₅ (CH ₃ ) ₂

0307-71 CH (CH _{3) 2}

CH _{(CH3) 2} CH (CH _{3) 2}

COOCH · cA

COOCHCOOCH-, cy

3

20

167

344/94 H

103

Table 3 - continued

Example # R ¹ R ²

R '

Heating temperature;

(° C)

L 52 ru C ^on L .. ₂ L ₂ .. ₅

L 53

CHn CHn

L56 ^C 2 ^H 3 O ^CH

155 <1

157

158

59

160

J-COOCH

144

COOCHq

COOCH-.

COOCH

56 //

h ₂ - ch ₃

COOCH-.

-N (CH ₃ ) ₂ ch ₃

FROM \

COOCH-, ik ^:

CKoc ₂ h ₅

183

190

CH ₃ C ₃ H _; ^ C00C ₂ H ₅

20

CHV344 / 94II

104

Table 3 - continued

Example # _Rj_R ^ _R ^ _ Melting point (° C)

L ck _{3 to 3} to ₇

134

162

163

164

165

166

167

168

169 ^Cri 3 0 ^C 3 ^h 'of cj-: ₃ oc ₃ to ₇ ^CH 3 0 ^C 2 ^H 5 ch ₃ oc ₂ h ₅ ch ₃ oc ₂ h ₅ ck ₃ oc ₂ k ₅ ch ₃ oc ₂ h ₅ ch ₃ oc ₂ h ₅ ar

ABOUT

C00C ₃ r ₇

HLI

CH1 22

125 / C00C ₂ r ₅

166-167

C00CH _q

E

131-132

F

147-148

186-137

125-126 '123-124

V344 / 94H

105

Table 3 - continued

Example ³ č.Rj_R _Teplota point (° C)

70 ch ₃ oc ₂ h ₅

7 L

CH ₂ O ₂ H _-5 .

172 ^Cr- 3 OC2H5

173

174

CHg 0 ^C 2 ^K 5

175

CH _{2 O} C ₂ H ₅

6

Chg QC ₂ H ₅

177

CH ₂ O C ₂ H ₅

Cl

183175152172

147

3

178

155

189

76

153

173

148

134

183

156

V344 / 94H

106

Table 3 - continued

EXAMPLE No._Rj_R ^ _Fp_Temperature (° C) t 78 ch ₃ oc ₂ h: ₅

CH ·

162-163 '9

CH 3 0C ₂ '5

· C '

146-147

ISO

C 7 OCH ₃

COOCHg

129-130

L ^C 3 ^H 7

OCH,

Cl ·

150-151 ^C 3 ^H 7

OCHBr

Cl ·

130-13 '

133 ^C 3 ^H 7

QCHg

Cl ·

COOC ₃ H ₇

135-136

186 ^C 3 ^H 7

OCHCl ·

C00C ₂ Hg

126-127

185

C ₃ H ₇

OCHCl

116-117

V3-14 / 94H

1 () 7

Table 3

Example #

L S ó continued

R '

R ^z

R ³ _ Melting point (° C) c ₃ h ₇ and ₃

- COOC ^ ^ p

ΙΪΗ "

129-130

CH

Cl ^C 3 ^H 7

OCH \ _ // \

CH156 '157

OC

IS S

139

190

191

192

193 ^C 3 ^H 7 ^C 3 ^H 7

C (H) +

OCHOCHOCH-

Cl

117-118

139- 140

115-116

C ₃ H ₇ 0C'ri ₃ C ₃ H _{7 OCH3} C ₃ H _{7 OCH3} ^CH2 ~ ^ '

C1

183-184

130-131

108- 109

V344 / 94H

ΙΟΝ

Table 3 - continued

Example No. R ¹ R ² _ C_Temperature (° C)

/ cooc ₂ ? ₅

122-123

123-129

19 'c; -: ₃ c ₄ h ₉ | j | (

97

198

CH-OC-H

4''9

QQ

CH, 0C..H <‘• 9

CH3r

COOCqH105

200 t H 3 0 C ₄ H ₉

201

CK ₃ oc ₄ h ₉

137

V344 / 94II

109

Table 3 - continued

Example # R ¹ R ²

2

203

206

CK ₃ 0C ₄ H _{5 g of} chloro 0C ₄ H _g C - ₂ ° C _{for 4} hours ₉

205

C r. j OC H

206

0C ₂ K ₅

207 ^{° C} 2 ^H 5

208 '2 “5

209

CH

Cr

C: ~: ~ ₂

Melting point

C C] _s / <<OOCH ₃

35

108

209

V344 / 94H

Table 3 - continued

Example # _R? _R ^ _R ^ _ Melting point (° C)

10

2L3

207 i 37

Cl

17?

24

153

150

V344 / 9411

Table 3 - continued

Example #

R '

R ²

R ³ _ Melting point (° C)

IS

CH ₂ -CH = Cn ₂ OCH '·,

19

CH ₂ -CH ₂ = CH ₂ CN ₂

220 ^Ch; 3 OCHch ₃ and ₃

CH ^ 'C.TCr, OCH-,

103

30

196

3O

30

223

CH

COOC

226

225

CHochf ₂

179

CKD

171

V344 / 94II

112

Table 3 - continued

Example No._Rj_Rf_Rf_Temperature (° C)

26

-ck ₂ -c .-: = ch ₂ and ₃

227 hp ₅

OCH?

Cl ·

223 ^C C ₃ H ₇

29

CH ·

OCn230

23i

Cl ·

COOC ₃ H ₇

Cl ·

162

133 ^- What? ~ C n - C c. ? OC n -

V344 / 94II

113

Table 3 - continued

Example # _Rj_R ^ _R ³ _ Melting point (° C)

23i

-CH ₂ -CH = CH ₂ O ^C '' ^: 3

235

OCH,

23o 2 ⁿ 5

237

238

239 c ₂ h ₅ 0ch ₃

2i0

C ₂ n ₅ OCH ₃

2M c ₂ to ₅ and ₃

nr ^ co ₂ ^c 2h ₅

140-141

CH

V344 / 94II

114

Table 3 - continued

Example # R ¹ R ² R ³ Melting point (° C)

i 60

4 7

157

26

23

204

1 9

147

V344 / 94ÍI

115

Table 3 - continued

Example # _R_J_C_R ^ _ Melting point (° C)

250

Ch'g OC ^ Hg

C 1

CH25 L

CK ₃ 0C ₄ H ₉

OCr j

· ^ C

123-124

252 cc ₂ h ₅ cl ·

152-153

253 ^{° C} 2 ^H 5

Cl ·

C 25 C 25

116-117

254 C ₂ h ₅

C 1 cl ·

145-145 ^0C 2 ^H 5

Cl

CHOCF

132-133

256 C ₂ H ₅

Cl ·

88-8?

V344 / 94II

Ιό

Table 3 - continued Example No. R ¹ R ²

R ^J

Melting point (° C)

257 C ₂ h _p

53

0C ₇ H

2 ·· 5

259

-CH ₂ -CH: CH ₂ ^OC 2 ^H 5

128

129

260

_-CH2-CH = _{CH2 OC2 H5} COOC ₂ hours ₅ IMT

CH79

114

15

104

261

-ck ₂ -ch = ck ₂ oc ₂ to ₅

262

-c.-. ₂ ~ Cr. = C.-. ₂ oc ₂ h ₅

263

-CK ₂ -C'ri = CK ₂ 0C ₂ H _s

264

-CH ₂ -CH = CH _{2 or 2} h ₅

Sr

121

122

107

108

123

124

V344 / 94H

117

R ³ _ Melting point (° C) ci

Table 3 - continued Example No. R ¹ R ²

5

266

131-132

267

-ch ₂ -c ~ = ch

263

-c: -: ₂ -Cn = c: -:

269

-ch ₂ -ch = ch

270

-cf ₂ -ch = ch

First

- C H 2 C n = C H 2

272

-ch ₂ -ch = ch ₂ oc ₂ h ₅

C 1 /

CHl L S-1 1 9

OC ₂ H _with ^OC 2 ^b; 5

0C 2 * “S

0 ^ 5 oc ₂ to ₅ cc ₂ h ₅

CFOCr- ₃ i 10-ii 1

123-124

Cl

103-104> 250

V344 / 941- |

I 18

Table 3 - continued

Example No. R ¹ _FU_R ^ _ Melting point (° C)

273 ch (ch ₃ ) ₂ oc ₂ h ₅

COOCH-1 pA

188-190

7A

CK (CK ₃ ) ₂ 0C ₂ ^h with cooc ₂ h ₅

iFit

230-231

275

CK (CH ₃ ) ₂ 0 ^c 2 ^H 5

7 ô

CH _{(CH3) 2} ^0C 2 ^H 5

129-130

277 • ck (ch ₃ ) ₂ 0c ₂ to ₅

278

CK (Cr: ₃ ) ₂ C ₂ n ₅

279

CH (CK ₃ ) ₂ oc ₂ h ₅

280

CH (CH ₃ ) ₂ 0 ^c 2 ^H 5 cr

V344 / 94II

I 19

Table 3 - continued R ¹ R *

R ³ _ Melting point (° C)

L cr: <cr: ₃ ) _{2 to 2} to ₅

282 ch (ch ₂ ) ₂ oc ₂ h ₅

COOCH106

124

283

- (ch ₂ ) ₃ -cci-: ₃ and ₃

284

- (C r ₂ ) ₃ - OC H -j 0 C r ₃ cooc ₂ 'r-: ₅ rf <<5

285 '- (ch ₂ ) ₃ -och ₃ and ₃

F

12c

br

127

286

- (C H 2) 3 '0 C r 2 o C r. 3

16

287

- (ch ₂ ) ₃ -oc ?: ₃ and ₃

288

- (ch ₂ ) ₃ -och ₃ and ₃

13

V344 / 94II

120

Table 3 - continued

Example No. R * R ² _R ^ Melting point (° C)

289

- (CC ₂ ) ₃ -OCK ₃ 0CK ₃

290 "(CHgIg-OCn ₃ 0 CH ₃ ? Q 1

- (CH ₂ ) ₃ -OCn ₃ 0Ci _{3 3} Q ₇ nC ₃ H ₇ 0C ₂ n ₅

3 n - C ₃ H ₇ 0 C g H ₅

- 105

1 4

213

C ri 294 n-Cgí '. y OCgHc;

106

107

Sr

5 n ~ C ₃ K y OC ₂ H ₃ o127

123

296 n-Cgh'y 0C ₂ Kg

COOC-, ας α

V344 / I-94i

121

Table 3 - continued R ¹ R ²

R_Temperature (° C)

297 nC ₃ K ₇ 0 ^C 2 ^H 5

C t

Cl ·

132-135

298 nC ₃ H ₇ ^0C 2 ^H 5

C L a

CH133-140

299 nC ₃ H ₇ ^0c 2 ~ 5

300 n - C ₃ n ₇ 0 C ₂ H 5

301 η-Ο ₃ ° 2 ₇ ° ^C 2 ^: ~ ^: 5

302 nC ₃ H ₇ 0C ₂ H ₅

303

CH (CH ₃ ) ₂ ock ₃

-ARE YOU

105-109

154-157

130-1

150- 151

304

COOC ₂ K ₅

Ch '(CH ₃ ) ₂ OC ₃ [|

160-16 1

CHV344 / 94H

122

Table 3 - continued

Example No. R ¹ R ² _ C_Temperature (° C)

305

CH (CH-) ₂ OCH ₃

-14 8

30o

CH (CH 2) 2 OCH-,

307

C H (C-t) 2 OCH 2

305 ch (c.-.-) ₉ Och. 3

309

C H (C, - .2) 2 Oc H 3

150

310

0.1 (.0.3) 2 Och-j

311 ch (ch3) ^ Och3

312

CH _{(CH3) 2 OCH3}

-150

-144

35

150

145

L 1 6

V344 / 94II

123

Table 3 - continued

Example # Ff R ² _ R ³

Melting point (° C)

313

CH (CH ₃ 1 ₂ OCHC)

/ Ä

125-12S

1.6

CH0CH (CH ₃₎ 2

COOCHn

O95-97

CHBr

TV

OCH (CH ₃ ) ₂ \ /

158-160

COOC ₂ K ₅

317

318

19

320

CHCHCHCHCHoch (c: -; ₂ ) ₂ \ __ /

OCF and ch ₃ and ₂

0CH (CH _{3) 2}

CF

CHM0CKCCK _{3) 2} \ _ _of

C00CHV £ d

152- 153

150-152

128-120

150-152

117-113

344/94 H

124

Table 3 - continued

Example # R ¹ R ²

L

ΟΠRΟ HCl · '

Melting point (° C)

130-132

oc ₂ h ₅

323 • 2S

OCH

4 S · · 5 O

172-173

II

- / ^ COOC

325

326

327

323

329

330

-ch ₂ -ch = ch ₂ oc ₂ h ₅ ch (ch ₃ ) ₂ oc ₂ h ₅

- (ch ₂ ) ₃ -och ₃ and ₃ nC ₃ H ₇ oc ₂ h ₅

- _with / ^ <00CH ₃

127-130

127-130

CH (CH ₃ ) ₂ ock ₃

CHOC'ri (CH ₃ ) ₂

156-157

193 - 200 ch (ch ₃ ) ₂ oc ₂ h _p

C00C _q H ₇ -n

Cl · ⁱ²² - ^{i2 <}

V344 / 94H

125

Table 3 - continued

Example # R ¹ R ² _ »m» Melting point (° C)

331 (c: -: ₂ ) _{3 - 3} and ₃

COOCqHy -n o332

0C ₂ H ₅

C00C-> H ₇ -n

28

30

333

CK (Cn ₃ ) ₂

OCHoCOOCgHy - n.

50

334

CHcooc ₂ hours ₇ -.och _{(CH3) 2} {3 /

335 ^C -2 ^H 5

OCH.

C00C-, H ₇ -n

145

336

CHoc ₂ h ₅

paralyze

CT

Ho- 1

36

337

CHoc ₂ h ₅

338

CH ·

0C ₄ H ₉ - _n

176

142

143

V344 / 94H

126

Table 3 - continued

Example # _R? _R ^ _R ³ _ Melting point (° C)

339 ^c 2 ^h 5

CCH. ·

115-1 15

360 • ch ₂ - ch = ch ₂ t

c: -: ₂ to ₅ 0C

362

CHoc ₂ H ₅

363 c: -: ·

OCH,

366 CH.

365 CH.

oc ₃ h ₇

366 CH.

OCH q oc: -: f ₂ cooc: -: -,

COOC-H ₇ - n

COOCH-.

COOCHOOCFO161-163

N s 161

188

On the·

173

On the·

V344 / 94II

127

Starting materials of general formula jl

Example (11-1)

Stage 1:

NN-NH-CO-OC ₂ H ₅

HN-CO-C ₂ H ₅ (IX-1)

A mixture of 68.5 g (0.60 mol) of 5-methyl-1,3,4-oxadiazolin-2-one, 45.8 g (0.75 mol) of O-ethylhydroxylamine and 400 ml of water is heated under reflux for 12 hours under reflux and then the reaction mixture is concentrated. The residue is taken up in ethanol and concentrated again. The residue thus obtained is stirred with diethyl ether and the resulting crystalline product is filtered off.

77.5 g (74% of theory) of 1-ethoxyaminocarbonyl-2-propionylhydrazine of melting point 122 DEG C. are obtained.

about

Stage 2:

- oc ₂ h ₅ ^C 2 ^H 5

A mixture of 75.5 g (0.43 mol) of 1-ethoxyaminocarbonyl-2-propionylhydrazine, 17.5 (0.44 mol) of sodium hydroxide and 300 ml of water is heated under reflux for 12 hours. After cooling the reaction mixture, the pH was adjusted to 3-4 by addition of concentrated hydrochloric acid and the mixture was concentrated. The residue was triturated with ethyl acetate and sodium chloride which remained

V344 / 94I i

128 in the undissolved state, is filtered. The filtrate is concentrated, the residue is triturated with diethyl ether and the crystalline precipitated product is collected by filtration.

37 g (55% of theory) of 4-ethoxy-5-ethyl-2,4-dihydro-3H-1,2,4-triazol-3-one with a melting point of 93 [deg.] C. are obtained.

Example (II-2)

(II-2)

A mixture of 40 g (0.31 mol) of 5-propyl-1,3,4-oxadiazolin-2-one, 109 g of an aqueous solution of methylamine (32%, 1.125 mol of CH ₃ NH ₂ ) and 500 ml of water is heated for 12 hours and then the mixture is concentrated. The residue is taken up in ethanol and the ethanol solution is concentrated again. The residue thus obtained is stirred with diethyl ether and the product obtained in crystalline form is filtered off.

31.7 g (72% of theory) of 4-methyl-5-propyl-2,4-dihydro-3H-1,2,4-triazol-3-one with a melting point of 86 ° C are obtained.

Example (II-3)

H N '

I

N.

N - N (CH ₃ ) ₂

856 g (4.0 mol of β-diphenyl carbonate) are dissolved in 588 g of ethylene chloride, while 245 g (4.0 mol) of dimethylhydrazine (98%) are added dropwise while cooling with water, followed by gentle heating and stirring for 4 hours. at 60 ° C.

V344 / 94H

129

After cooling to 20 ° C, 200 g (4.0 mol) of hydrazine hydrate was added dropwise and the mixture was further stirred for 12 hours. The reaction mixture is heated to 70-80 ° C and further stirred for about 1 hour. The cooled solution was distilled in vacuo to remove ethylene chloride and water (bottom temperature finally 100 ° C). The phenol solution of dimethylcarbodihydrazide obtained above was added dropwise to 424 g (4.0 mol) of trimethyl orthoformate in the course of 90 minutes at reflux temperature (about 102 DEG C.). After distillation of the resulting methanol by distillation, phenol was distilled off in vacuo, then 282 g of the product mixture at a head temperature of 85-105 ° C. This mixture is boiled with 600 ml of acetone and after filtration at boiling point, the filtrate is cooled. The product obtained in crystalline form is isolated by filtration.

71 g (14% of theory) of 4-dimethylamino-2,4-dihydro-3H-1,2,4-triazol-3-one with a melting point of 127 [deg.] C. are obtained.

For example, the compounds of Formulas II and IIa 'listed in Table 4 below can also be prepared in an analogous manner to those described in Examples 11-1' to II-3.

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130

Table 4

Examples of prepared compounds of formula II

Example # R ¹ R ² Melting point (’C) II-4 ^C 3 ^H 7 ch ₃ 48 II-5 CH (CH-j) ₂ CH ₃ 118 II-6 CH CH ₃ 139 II-7 ^C 2 ^H 5 ^C 2 ^H 5 117 II-8 c ₃ h ₇ ^C 2 ^H 5 42 - 45 ' II-9 CH _{(CH3) 2} ^C 2 ^H 5 102 11-10 ^C 2 ^H 5 97 II-II ^C 3 ^H 7 (amorphous product 11-12 ch (ch ₃ ) ₂ ^C 3 ^H 7 91 11-13 ch ₃ CH _{(CH3) 2} 92 11-14 C ₂ ^h 5 CH _{(CH3) 2} (amorphous product) 11-15 ^C 3 ^H 7 CH _{(CH3) 2} (amorphous product) 11-16 ch (ch ₃ ) ₂ CH _{(CH3) 2} 168 11-17 ^C 2 ^H 5 CH ₃ 134 11-18 CH. 159

V344 / I-94i

131

Table 4 - continued

Example # R ¹ R ² Melting point (° C) 11-19 0CH ₃ CH ₃ 178 Π-20 0CH ₃ ^C 2 ^H 5 140 11-21 0CH ₃ ^C 3 ^H 7 127 11-22 0CH ₃ ch (ch ₃ ) ₂ 130 11-2 3 OCH ₂ C ₆ H ₅ ch ₃ 106 11-24 ^C 2 ^H 5 150 11-25 C3H7 130 11-26 OC ₂ H ₅ ^c 3 ^h 7 72 11-27 CH _{(CH3) 2} 121 11-28 CH ₃ CH _q 4 9 50 II- 29 ^C 2 ^H 5 ^C 4 ^H 9 76 11-30 y? 1 (amoríhy product) 11-31 OCH ₃ ^C 4 ^H 9 100

11-32 _X .2 >> C ₄ H _g 66

11-33 CH ₃ —ACA. 68

V 344-t / 94II

132

R ^z

Melting point (° C)

Table 4

Example #

continue

11-34

11-35

11-36

11-37

II- 38

Π- 39

11-40

11-41

11-42

II-43

11-44

11-45 ^C 2 ^H 5 ^C 3 ^H 7

130

154

N _{(CH3) 2} Ch ' ₃ 153 N _{(CH3) 2} ^C 2 «5 114 N _{(CH3) 2} ^C 3 ^H 7 1CQ N _{(CH3) 2} ch (ch ₃ ) ₂ 100 ch ₃ N _{(CH3) 2} 80 N _{(CH3) 2} 134 CH _{(CH3) 2} NHCH _{(CH3) 2} 205 N _{(CH3) 2} N _{(CH3) 2} 93 o ₂ h ₅ N _{(CH3) 2} > 0

V344 / 9411

13.3

Table 4 - continued

Example No._Rj_Rf_Temperature (° C)

11-46

CH145

H-47

CH163

11-48

102

11-49 OCH ^ 136 - 1 11-50 ch ₃ ^C 6 ^H 5 11-51 nh ₂ H 192 11-52 nh ₂ ch ₃ 230 H-53 nh ₂ cf ₃ 163 II-54 NHCH ₃ CH _{(CH3) 2} 105 11-55 NHCH ₃ 95

V344 / 94H

II '> 4

Table 4 - continued

Example No. _R ¹ _B1 _ Melting point (° C)

11-56

11-57

11-58

11-59

II-N6

11-61

11-62

11-63

NH.

NH,

NHCH.

^CH 2 ^C 6 ^H 5

NHCH.

NHCH.

NHCH.

NH,

11-64

NH.

11-65

NH,

11-66

NH.

c ₂ h ₅ c ₃ h ₇

NHCH ₂ h ₅

H n (ch ₃ ) ₂

Cl

170

147

137

125

133

129

248

176

183

210

V344 / 94II

Table 4 - continued

Example # R ¹ R ² Melting point (’C) 11-67 NHCH ₃ 5 ', 2' 101 11-68 nh ₂ n (c ₂ h ₅ ) ₂ \ 19 6 11-69 NH ₂ N- _ / 233 II-7a nh ₂ CH _{(CH3) 2} 172 11-71 mh ₂ C _{(CH3) 3} 261 11-72 nh ₂ CH ₂ CH ₂ OCH ₃ 98 11-73 nh ₂ C (CH ₃ ) ₂ C ₂ H ₅ 213 11-74 nh ₂ NHC _o H _c 2 5 220 11-75 nh ₂ OCH ₃ T (amorphous product) 11-76 nh ₂ CH ₂ OCH ₃ 134 11-77 nh ₂ CH ₂ OC ₂ H ₅ 104 11-78 N _{(CH3) 2} CH ₃ 153 11-79 -CH _{2 -} Z \ Cl Cl C 2 ^H 5 105 11-80 -ch ₂ ch (ch ₃ ) ₂ C 2 ^H 5 105

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136

Table 4 - continued

R ¹ R ² Melting point (° C) rriKiao c. 11-81 ^C 6 ^H 5 H 183 11-82 N _{(CH3) 2} ch (ch ₃ ) ₂ / (amorphous for duct) 11-83 NKCH ₃ ch ₃ 114 11-84 nh ₂ ch ₂ c ₆ ^h 5 168 11-85 nh ₂ N _{(CH3) 2} 207 11-86 nh ₂ C.H. 6 5 230

11-87

NH,

223

11-88

11-89 nh ₂

NHCH

NHCH _{(CH3) 2}

NHCH _{(CH3) 2}

152

120

11-90

254

11-91 N _{(CH3) 2}

In 34 4/941

137

Table 4 - continued Example B ^ r ² _ Melting point (° C)

iI-92 ^CH 2 ^C 6 ^H 5 11-93 ^C 3 ^H 7 11-94 ^C 6 ^H 5 11-95 C _{(CH3) 3} 11-96 CH,

11-97

H lll H 48 o ₂ h ₅ 124 ^C 2 ^H 5 158 H 157 c ₂ h ₅ 108

11-98 c ₂ hrs ₅ 132

11-99 -CH ₂ CH = CH ₂

II-100C ₆ H ₅

108

150

116

V 34-1 / 9-) 11

I 38

Table 4

Example #

11-102

11-103

11-104

11-105 continued

R ¹

Melting point (° C)

11-106

11-107

11-108

11-109

C (CH

CH "CH-CH" Br ^and I

br

CH.

194

111

CH ₂ and ₃

104

V344 / 94H

139

Table 4 - continued

Example No._Rj_Rj_Temperature (° C)

-CH ₂ OC ₂ H ₅ 102

II-III

-CH ₂ OCH ₃ I ²

CH-O-C-H. 119

2 5

11-113

-N _{(CH3) 2} 130

CH.

11-114 NH

FROM

-N

186

11-115 NH ₂ c ₂ h ₅

165

V344 / 94H

140

R ²

Melting point (° C)

Table 4

Example #

continuation nh ₂

N ^C 2 ^H 5

186

PP '

11-117 / \

NH ₂ _n by 267 \ _ /

11-118

CH

-och ₃

144

V344 / 9411

141

The compound shown in Table 4 as Example 11-118 can also be prepared, for example, as follows:

ABOUT

50.2 g (0.33 mol) of hydrazinic acid phenyl ester and 36.6 g ((0.33 mol); 90%) of Ο, Ο, Ν-trimethyliminocarbonate are mixed with 100 ml of o-dichlorobenzene at 40 ° C and the mixture was stirred at 60 ° C for 2 hours. The mixture is then slowly heated to 120 ° C while distilling off methanol, cooled again, and then heated again at 120 ° C under vacuum of an oil pump (1 Pa) to distill off the remaining volatile components (methanol, phenol and dichlorobenzene). Above 120 ° C, no product distills off crude and this is finally recrystallized from toluene.

7.5 g (18% of theory) of 5-methoxy-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 144 DEG C. are obtained.

The following Table 5 gives examples of hydrazine derivatives of formula (IX) which can be prepared in an analogous manner to that described in Example 11-1).

HN- CO - NH - R ¹

^HN-CO-R2 (IX)

V.344 / 94II

142

Table 5

Examples of hydrazine derivatives of formula IX

Example # R ' R ² IX-2 OCH-j C ₂ ^H 5 IX-3 och ₃ ^C 3 ^H 7 IX-4 och ₃ ch (ch ₃ ) IX-5 and ₂ c ₆ h ₅ CH} IX-6 C-H.

IX-7

IX - 8 ^C 3 ^H 7

IX-9

Sep-10

Sep-11

IX-12 C ₂ H ₅ ^C 3 ^H 7

CH _{(CH3) 2}

OCH.

^C 4 ^H 9 '4

Melting point (° C)

120

125

127

100

174

180

119

150

134

159

188

V344 / 94H

143

Table 5 - continued Example no. R ¹

R ² ix-13 and ₃

IX-14 ch ₂ -ch = ch ₂ ^C 3 ^H 7

IX-15

Melting point (° C)

140

134

Starting materials of formula (IV)

Example (IV-1)

6.4 g (0.05 mol) of 5-ethyl-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one are dissolved in 80 ml of tetrahydrofuran and the resulting solution is stirred under a nitrogen atmosphere. 1.8 g (0.06 mol) of sodium hydride (80%) are added. After stirring at 20 ° C for one hour, 7.9 g (0.05 mol of β-phenyl chloroformate) are added dropwise and the reaction mixture is stirred for 20 hours at 20 ° C. After concentration, the residue is taken up in methylene chloride, methylene chloride solution. The filtrate is concentrated, the residue is triturated with diethyl ether and the product which precipitates in a crystalline state is isolated by filtration.

V344 / 94H

144

4.5 g (36% of theory) of 5-ethyl-4-methyl-2-phenoxycarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 141 DEG C. are obtained.

In a similar manner to that described in Example IV-1 ', for example, the compounds of formula IV' as shown in Table 6 below can also be prepared.

V344 / 94II

145

Table 6

Examples of compounds of formula IV Example NO

Melting point (° C)

IV-2 ^C 3 ^H 7 ^C 3 ^H 7 ^c 6 ^H IV-3 och ₃ c ₆ h IV-4 CH ₃ ^C 3 ^H 7 c ₆ ^h IV-5 nh ₂ ^C 3 ^H 7 c ₆ h IV-6 nh ₂ CH ₃ c ₆ ^h IV-7 ^C 2 ^H 5 c ₆ ^h IV-8 oc ₂ h 5 5 ', 2' ^C 6 ^H IV-9 and ₂ ch = ch 2 ch ₃ ^C 6 ^H IV-10 ^C 4 ^H 9 ^C 6 ^H IV-11 CH ₃ c ₆ h

133

152

V344 / 94H

146

Table 6 - continued

Example # R ¹ R ² from Melting point (° C) IV-12 _NHCH3 ^C 2 ^H 5 ' ^C 6 ^H 5 IV-13 CH ₃ ch ₂ c ₆ h ₅ ^C 6 ^H 5 IV-14 CH ₃ NHCH _{(CH3) 2} ^C 6 ^H 5 IV-15 N (CH ₃₎ 2 N _{(CH3) 2} ^C 6 ^H 5

IV-16

^C 6 ^H 5

IV-17 0C.H _c 2 5 ^c 6 «5 TV-18 oc ₃ h _? ^C 2 ^H 5 ^C 6 ^H 5 IV-19 c ₂ h ₅ ^c 6 « ₅ IV-20 CH _{(CH3) 2} CH _{(CH3) 2} ^C 6 ^H 5 IV-21 0CH ₃ ^C 2 ^H 5 ^C 6 ^H 5 89 IV-22 C ₃ H 11 -n ^C 6 ^H 5 104

V344 / 94H

147

Application examples

In the following application examples, the known isocarbamide herbicide of the following formula A was used as a comparator:

HN N-CO-NH-CH ₂ CH (CH ₃ ) ₂ (A)

The formulas of the compounds of the invention which were used in the following application examples are given below (the numbering corresponds to the numbers in the Examples):

CH.

(4) c ₂ h ₅

V344Z94I1

148

(5)

(6) (2)

V344 / 94H

149

COOCH

OCH.

• SO _{2 -} NH - CO - N (12)

COOCH.

SO ₂ -HH-CO ₂ n (CH ₃ ) ₂

ABOUT

II

SO ₂ -NH-CO

SO ₂ N (CH ₃ ) ₂

o ₂ h ₅

OCH, 3 ^c 3 ^H 7

CH.

c ₂ h ₅ (13) (14) with ₂ -nh-co-nn ch, x->

(15)

N, ^C 3 ^H 7

V344 / 9.II I

150

COOCH-

(16)

COOCH ₃ ) - SO ₂ -NH-CO

(17)

SO ₂ N (CH ₃ ) ₂

SO ₂ -NH-CO-N

CH _{(CH3) 2} (18) ^C 2 ^H 5

(19)

V344 / 94H

151

N

X

N

CH.

(20)

COOCH.

N _{(CH3) 2} /

SO ₂ -HH-CO

N H

N - = oc ₂ hr ₅ (26)

COOCH.

/ c ₂ h ₅

SO ₂ -NH-CO

OC.H, X ²⁵

COOCH.

Sat ₂ -nh-co

N N '

I _

N ^C 3 ^H 7

CH _{(CH3) 2}

V344 / 94I1

152

(29) The

COOCH.

SO ₂ -NH-CO-n Ni i

N

N (CH,) / 2 3 (30) "3 ^H 7

Ο, _Η ς

- 2 5

N (32)

COOCH.

^C 4 ^H 9

CHSO ₂ -NH-CO-H

I

N (33) ^C 4 ^H 9

V344 / 94II

153

C., (34)

ABOUT

(35)

ABOUT

(39)

V344 / 94II

154

(40)

C00CH.

Sat ₂ -nh-co -

(9)

(36)

V 344/941 1

155

Example A

Preemergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To obtain a suitable active compound preparation, 1 part by weight of active compound is mixed with the indicated amount of solvent, the said amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

The seeds of the test plants are sown in normal soil and, after 24 hours, watered with the active compound. The amount of water per unit area is expediently kept constant. Concentration of the active ingredient in the formulation plays no role, only the amount of active ingredient applied per unit area is critical. After three weeks, the degree of damage to the plants is evaluated in% of damage compared to the development of untreated control plants. It means:

% = no effect (as in the untreated control)

100% = complete destruction of plants

For example, the compounds of Examples 2, 6, 8, 12, 13, 16, 17, 18, 19, 20, 26, 34, 37, 39 and 40 exhibit a significant superiority over the prior art in this assay.

Example B

Post-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To obtain a suitable active ingredient composition, 1 part by weight of active ingredient is mixed with the indicated amount of solvent, added

V344 / 94II

156 said amount of emulsifier and concentrate is diluted with water to the desired concentration.

The active ingredient is sprayed with test plants having a height of 5 to 15 cm in such a way that the required amount of active ingredient per unit area is always applied. The concentration of the spray suspension is selected such that the required amount of active ingredient is applied in each 1000 liters of water per hectare. After 3 weeks, the degree of plant damage was evaluated in% of damage compared to the development of untreated control plants.

It means:

% - no effect (as in the case of untreated control plants)

100% = complete destruction of plants

In this test, for example, the compounds of the examples of embodiment no. 2, 4, 5, 6, 7, 8, 12, 13, 14, 15, 16, 17, 18, 19, 20, 26, 27, 28, 29, 30, 32, 33, 34, 35, 37 39 and 40.

Example C

Test for Pyricularia oryzae (rice) / protective effect

Solvent: 12.5 parts by weight of acetone

Emulsifier: 0.3 parts by weight of alkylaryl polyglycol ether

To prepare a suitable active ingredient preparation, 1 part by weight of active ingredient is mixed with the stated amount of solvent and the concentrate is diluted with water and the amount of emulsifier to the desired concentration.

In order to test the protective activity, young rice plants are sprayed with the preparation of the active ingredient until the drops are dripped. After the spray layer has dried, the plants are inoculated with a spore suspension of the fungus Pyricularia oryzae. The plants are then placed in a greenhouse at 100% relative humidity and 25 ° C.

V344 / 94II

157 days after the inoculation, the disease is evaluated.

In this test, for example, the compounds of the following examples have a good effect: 9, 12, 13, 20, 30, 31, 32, 33, 34, 35, 36 and 37.

Example D

Test for Pyricularia oryzae (rice) / systemic effect

Solvent: 12.5 parts by weight of acetone

Emulsifier: 0.3 parts by weight of alkylaryl polyglycol ether

In order to prepare a suitable active ingredient preparation, 1 part by weight of active ingredient is mixed with the indicated amount of solvent and the concentrate is diluted with water and said amount of emulsifier to the desired concentration.

To test for systemic properties, 40 ml of the active ingredient preparation was poured into a single soil in which rice plants were planted. 7 days after treatment, the plants are inoculated with an aqueous spore suspension of the fungus Pyricularia oryzae. The plants are then placed in a greenhouse where they are maintained at 25 ° C and 100% relative humidity until evaluation.

days after inoculation, the disease is evaluated.

In this test, for example, the compounds of the following examples show excellent activity: 9, 12, 13, 20, 30, 31, 32, 33, 34, 35, 36 and 37.

The results of the described assays are shown in Tables A through

D.

V344 / 94II

158

Table A: Preemergence test / glass

effective substance applied quantity (g / ha) Setaria Chenopodium Matricaria Purslane Solanum > A 500 0 50 0 40 0 '6 250 100 80 95 70 90 2 250 100 70 100 90 80 with; 250 90 90 95 100 80 '12 250 100 90 95 95 90 13 500 95 90 90 90 100 '16 250 100 90 95 90 100 17 .. 500 100 80 80 .95 90 '18. 250 90 100 90 100 1Ô0 '19 250 100 100 95 100 95 '20 250 95 100 70 100 90 26 250 100 90 90 90 95 27 250 100 90 95 90 100 28 250 100 95 70 90 90 '28' 250 95 80 90 90 95 34 250 100 90 100 90 37 125 95 80 70 50 90 39 ' 125 90 70 80 80 90 40 ' 250 100 95 90 100 95

V344 / 94II

159

Table B: Postemergence test / glass

effective substance applied quantity (g / ha) Amaranthus Datura Galinsoga sinapis Solanum A 1000 0 10 60 20 0 "4th 125 100 90 95 95 95 5th 250 100 80 90 80 '6 125 100 100 95 100 100 '2 125 100 95 95 100 95 7 ' 250 95 80 100 80 '8 125 100 90 90 95 90 12 ' 125 90 100 80 100 100 '13 125 100 95 95 90 95 '14' 125 40 90 90 90 15th 125 90 90 80 90 16. ' 125 100 100 95 100 100 '17 125 70 90 95 95 Ί8 125 30 90 80 100 95 Ί9. 125 95 100 100 100 95 20 ' 125 95 90 60 95 90 26 ' 250 100 100 100 100 100 '27' 125 95 95 95 90 95 28; 125 100 95 95 100 95 29 ' 125 100 95 90 95 90 .'30} 125 80 80 90 90

V344 / 94II

160

effective substance applied quantity (g / ha) Amaranthus Datura Galinsoga sinapis Solanum 32 ' 250 80 80 90 90 90 33 ' 125 80 90 90 95 90 34 ' 250 90 80 90 100 95 35 ' 125 100 90 100 100 90 '37' 60 100 95 60 100 100 '39' 60 100 95 60 95 95 40 125 100 100 100 100 100

Table B: Postemergence test / glass (continued)

effective substance applied quantity (g / ha) Amaranthus Datura Galinsoga sinapis Solanum , and 1000 0 10 60 20 0 '4; 125 100 90 95 95 95 about; 250 100 80 90 80 6 125 100 100 95 100 100 '2 125 100 95 95 100 95 T 250 95 80 100 80 '8' 125 100 90 90 95 90 12 ' 125 90 100 80 100 100 13 125 100 95 95 90 95 '14' 125 40 90 90 90

V344 / 94H

161

effective substance applied quantity (g / ha) Amaranthus Datura Galinsoga sinapis Solanum 15 125 • 90 90 80 90 16 125 100 100 95 100 100 17 125 70 90 95 95 18 ' 125 30 90 80 100 95 19th 125 95 100 100 100 95 20> 125 95 90 60 95 90 26: 250 100 100 100 100 100 27 ' 125 95 95 95 90 95 28. ' 125 100 95 95 100 95 '29' 125 100 95 90 95 90 '30 125 80 80 90 90 32 ' 250 80 80 90 90 90 '33) 125 80 90 90 95 90 X 250 90 80 90 100 95 35; 125 100 90 100 100 90 37 60 100 95 60 100 100 .'39; 60 100 95 60 95 95 40 ' 125 100 100 100 100 100

V344 / 94II

162

Table C: Pyricularia-test (rice) / protective

Active substance effective concentration degree of effect in% by pr.č. substances in% unprocessed control 9 0,025 90 12 0,025 90 13 0,025 90 20 0,025 70 30 0,025 90 31 0,025 90 32 0,025 90 33 0,025 70 34 0,025 70 35 0,025 80 36 0,025 90 37 0,025 90

V344 / 94H

163

Table D: Pyricularia-test (rice) / systemic

Active substance Amount applied in mg degree of effect in% by pr.č. active substance per 100 cm ² • unprocessed control 9 100 100 12 100 100 13 100 90 20 100 100 30 100 100 31 100 100 32 100 100 33 100 80 34 100 90 35 100 100 36 100 100 37 100 86

V344 / 94

Claims (5)

PATENT CLAIMS Sulfonylaminocarbonyltriazolines of the general formula J R ³ - SO NH-CO-N N - Ε- Ktorom in which R ^{@ 1} is hydrogen, hydroxy, amino, optionally fluorine, chlorine, bromine, cyano, (C1 -C4) alkoxy, (C1 -C4) alkylcarbonyl or (C1 -C4) alkoxycarbonyl; a (C 1 -C 6) alkyl group optionally substituted by a fluorine atom, a chlorine atom and / or a bromine atom substituted by a C 3 -C 6 alkenyl group or a (C 3 -C 6) alkynyl group, optionally a fluorine atom, a chlorine atom a bromine atom and / or a (C1-C4) alkyl-substituted cycloalkyl group of 3 to 6 carbon atoms, optionally a fluorine atom, a chlorine atom, a bromine atom, a cyano group, a nitro group, a C1 -C4 alkyl group, a trifluoromethyl group, C 1 -C 4 alkoxy and / or alkoxycarbonyl (C 1 -C 4) -alkoxy substituted by C 1 -C 3 -alkyl, optionally fluorine, chlorine, bromine, cyano, nitro, (C 1 -C 4) alkyl, trifluoromethyl, alkoxy C 1 -C 4, fluoro or and / or chloro substituted with C 1 -C 3 alkoxy, C 1 -C 4 alkylthio, fluoro or / and chlorine substituted C 1 -C 3 alkylthio In 544 / 94II C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, and / or C 1 -C 4 alkoxycarbonyl substituted in the alkoxy moiety with a phenyl, optionally a fluorine atom, a chlorine atom, a cyano group, a phenyl group, (C 1 -C 4) alkoxy or (C 1 -C 4) alkoxycarbonyl substituted by C 1 -C 6 alkoxy, (C 3 -C 4) alkenyloxy, optionally fluorine, cyano, (C 1 -C 4) alkoxy, or (C 1 -C 4) alkoxycarbonyl substituted by C 1 -C 4 alkylamino or (C 1 -C 4) dialkylamino; R ² is hydrogen, hydroxy, mercapto, amino, or by F, Cl, Br, cyano, cycloalkyl having 3 to 6 carbon atoms, alkoxy of 1 to 4 carbon atoms or alkoxycarbonyl having 1 to 4 carbon atoms in the C 1 -C 6 -alkyl, optionally fluorine, chlorine, bromine and / or C 1 -C 4 -alkyl substituted by C 3 -C 6 -cycloalkyl, cyclohexenyl, optionally fluorine, chlorine, bromine, cyano, nitro, C 1 -C 4 alkyl, trifluoromethyl, C 1 -C 4 alkoxy, and / or C 1 -C 4 alkoxycarbonyl in the alkoxy moiety substituted by C 1 -C 3 phenylalkyl carbon in the alkyl moiety, optionally fluorine atom, atom m is chlorine, bromine, cyano, nitro, C 1 -C 4 alkyl, trifluoromethyl, C 1 -C 4 alkoxy, fluorine and / or chlorine substituted by C 1 -C 3 alkoxy, C 1 -C 4 alkylthio carbon, fluoro and / or chloro substituted alkylthio of 1 to 3 atoms V344 / 94II 166 carbon, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl and / or C 1 -C 4 alkoxycarbonyl substituted in the alkoxy moiety with optionally substituted phenyl, optionally fluorine, chlorine, cyano, 1-alkoxy (C 1 -C 4) alkoxycarbonyl or (C 1 -C 4) alkoxycarbonyl substituted by C 1 -C 6 alkoxy, (C 1 -C 4) alkylamino or (C 1 -C 4) dialkylamino; R ³ represents a moiety of the formula wherein R ⁴ and R ⁵ are the same or different from each other and are hydrogen, fluorine, chlorine, bromine, iodine, nitro, C 1 -C 6 alkyl optionally substituted by fluorine, chlorine, bromine, cyano, carboxy, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkylaminocarbonyl, C 1 -C 4 dialkylaminocarbonyl, hydroxy, C 1 -C 4 alkoxy, formyloxy (C 1 -C 4) alkylcarbonyloxy, (C 1 -C 4) alkoxycarbonyloxy, (C 1 -C 4) alkylaminocarbonyloxy, (C 1 -C 4) alkylthio, (C 1 -C 4) alkylsulfinyl; alkylsulfonyl having 1 to 4 carbon atoms, dialkylamine an alkylsulfonyl group having from 1 to 4 carbon atoms V344 / 94I1 167 parts, C 3 -C 6 cycloalkyl or phenyl; (C 2 -C 6) alkenyl optionally substituted by fluorine, chlorine, bromine, cyano, (C 1 -C 4) alkoxycarbonyl, carboxy or phenyl; (C 2 -C 6) alkynyl optionally substituted by fluorine, chlorine, bromine, cyano, (C 1 -C 4) alkoxycarbonyl, carboxy or phenyl; (C 1 -C 4) alkoxy optionally substituted by fluorine, chlorine, bromine, cyano, carboxy, (C 1 -C 4) alkoxycarbonyl, (C 1 -C 4) alkoxy, (C 1 -C 4) alkylthio, (C 1 -C 4) alkylsulfinyl or (C 1 -C 4) alkylsulfonyl; (C 1 -C 4) alkylthio optionally substituted by fluorine, chlorine, bromine, cyano, carboxy, (C 1 -C 4) alkoxycarbonyl, (C 1 -C 4) alkylthio, (C 1 -C 4) alkylsulfinyl or (C 1 -C 4) alkylsulfonyl; (C 3 -C 6) alkenyloxy optionally substituted by fluorine, chlorine, bromine, cyano or (C 1 -C 4) alkoxycarbonyl; (C 2 -C 6) alkenylthio optionally substituted by fluorine, chlorine, bromine, cyano, nitro, (C 1 -C 3) alkylthio or (C 1 -C 4) alkoxycarbonyl; (C 3 -C 6) alkynyloxy, (C 3 -C 6) alkynylthio or -S (O) _P -R ⁶ , where p is 1 or 2; and V344 / 94II 168 R ⁶ is C 1 -C 4 alkyl optionally substituted by fluorine, chlorine, bromine, cyano or C 1 -C 4 alkoxycarbonyl; (C 3 -C 6) alkenyl, (C 3 -C 6) alkynyl, (C 1 -C 4) alkoxy, (C 1 -C 4) alkoxyalkylamino, (C 1 -C 4) alkylamino, (C 1 -C 4) alkylamino C 1-4 alkyl, phenyl or -NHOR ⁷ , wherein R ⁷ is C 1 -C 12 alkyl optionally substituted by fluorine, chlorine, cyano, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl (C 1 -C 4) alkyl, (C 1 -C 4) alkylcarbonyl, (C 1 -C 4) alkoxycarbonyl, (C 1 -C 4) alkylaminocarbonyl or (C 1 -C 4) dialkylaminocarbonyl in the alkyl moieties; (C 3 -C 6) alkenyl optionally substituted by fluorine, chlorine or bromine; (C až-C) alkynyl, (C až-C cyk) cycloalkyl, (C až-C cyk) cycloalkylalkyl (C až-C,), (C až-C f) phenylalkyl (C až-C,), which is optionally substituted by fluorine, chlorine, nitro, cyano, (C1-C4) -alkyl, (C1-C4) -alkoxy or (C1-C4) -alkoxycarbonyl; benzhydryl or phenyl optionally substituted by fluorine, chlorine, nitro, cyano, C 1 -C 4 alkyl, trifluoromethyl, C 1 -C 4 alkoxy, C 1 -C 2 fluoroalkoxy, C 1 -C 4 alkylthio 4 carbon atoms, V344 / 94I is trifluoromethylthio or C1 -C4 alkoxycarbonyl; R ⁴ and / or R ⁵ are furthermore phenyl or phenoxy, C 1 -C 4 alkylcarbonylamino, C 1 -C 4 alkoxycarbonylamino, C 1 -C 4 alkylaminocarbonylamino, dialkylamino up to 4 carbon atoms in the alkyl moieties or a group of formula -CO-R ⁸ , wherein R ⁸ is C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 3 -C 6 cycloalkoxy, C 3 -C 6 alkenyloxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylamino carbon, C 1 -C 4 alkoxy, C 1 -C 4 alkoxyalkylamino or C 1 -C 4 dialkylamino optionally substituted by fluorine and / or chlorine, R ⁴ and / or R ⁵ are furthermore trimethylsilyl, thiazolinyl, C 1 -C 4 alkylsulfonyloxy, C 1 -C 4 dialkylaminosulfonylamino or -CH = NR ⁹ , wherein -CH = NR ⁹ ; R &lt; ⁹ &gt; is optionally fluorine, chlorine, cyano, carboxy, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfinyl or C1-C4alkylsulfonyl substituted C1-C4alkyl up to 6 carbon atoms; an optionally fluorine or chlorine substituted benzyl group; optionally fluorine or chlorine substituted alkenyl of 3 to 6 carbon atoms or alkynyl of 3 to 6 carbon atoms; optionally fluorine, chlorine, bromine, (C 1 -C 4) alkyl, (C 1 -C 4) alkoxy, trifluoromethyl, trifluoromethoxy or trifluoromethylthio substituted V344 / 94II 170 phenyl; optionally fluorine and / or chlorine substituted (C 1 -C 6) alkoxy, (C 3 -C 6) alkenoxy (C 3 -C 6) alkoxy or benzyloxy; amino, C 1 -C 4 alkylamino, C 1 -C 4 dialkylamino, phenylamino, C 1 -C 4 alkylcarbonylamino, C 1 -C 4 alkoxycarbonylamino, alkylsulfonylamino; a phenylsulfonylamino group optionally substituted by fluorine, chlorine, bromine or methyl; R ³ is further a group of the formula wherein R ¹⁰ represents a hydrogen atom or a C 1 -C 4 alkyl group, R ¹¹ and R ¹² are the same or different and are hydrogen, fluorine, chlorine, bromine, nitro, cyano, (C 1 -C 4) alkyl optionally substituted by fluorine and / or chlorine, (C 1 -C 4) alkoxy carbon optionally substituted by fluorine and / or chlorine, carboxy, C 1 -C 4 alkoxycarbonyl, dimethylaminocarbonyl, C 1 -C 4 alkylsulfonyl or C 1 -C 4 dialkylaminosulfonyl; R ³ is furthermore a group of the general formula V344 / 94H 171 where R ¹³ and R ¹⁴ are the same or different and represent a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a nitro group, a cyano group, an alkyl group having 1 to 4 carbon atoms optionally substituted by fluorine and / or chlorine or an alkoxy group having 1 up to 4 carbon atoms optionally substituted by fluorine and / or chlorine; then R ³ represents a group of the formula wherein R ¹⁵ and R ¹⁶ are the same or different from each other and are hydrogen, fluorine, chlorine, bromine, nitro, cyano, (C 1 -C 4) alkyl optionally substituted by fluorine and / or chlorine, (C 1 -C 4) alkoxy C 1 -C 4 alkyl optionally substituted by fluorine and / or chlorine, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl or C 1 -C 4 alkylsulfonyl optionally substituted by fluorine and / or chlorine a (C 1 -C 4) dialkylaminosulfonyl group or a (C 1 -C 4) alkoxycarbonyl group or a dimethylaminocarbonyl group; then R is a radical of formula V344 / 94H 172 where R ¹⁷ and R ¹⁸ have the same or different meanings and are hydrogen, fluorine, chlorine, bromine, C 1 -C 4 alkyl optionally substituted by fluorine and / or bromine, C 1 -C 4 alkoxy C 1 -C 4 alkyl optionally substituted by fluorine and / or chlorine is further understood to mean C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl or C 1 -C 4 alkylsulfonyl optionally substituted by fluorine and / or chlorine; are C1-C4 dialkylaminosulfonyl; then R ³ represents a group of the formula wherein R ¹⁹ and R ²⁰ are the same or different from each other and are hydrogen, fluorine, chlorine, bromine, cyano, nitro, C 1 -C 4 alkyl optionally substituted by fluorine and / or chlorine, C 1 -C 4 alkoxy C 1 -C 4 alkyl optionally substituted by fluorine and / or chlorine, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl or C 1 -C 4 alkylsulfonyl optionally substituted by fluorine and / or chlorine , (C1 -C4) dialkylaminosulfonyl, alkoxycarbonyl V344 / 94H A (C 1 -C 4) alkoxy or dimethylaminocarbonyl group; and A is oxygen, sulfur or N - Z ¹ , wherein Z ¹ is hydrogen, C 1 -C 4 alkyl optionally substituted by fluorine, chlorine, bromine or cyano, C 3 -C 6 cycloalkyl, benzyl, phenyl optionally substituted by fluorine, chlorine, bromine or a nitro group, a (C 1 -C 4) alkylcarbonyl group, a (C 1 -C 4) alkoxycarbonyl group or a (C 1 -C 4) dialkylaminocarbonyl group; then R ³ represents a group of the general formula R ²¹ where 21 22 R and R are the same or different from each other and are hydrogen, C1 -C4 alkyl, halogen, C1 -C4 alkoxycarbonyl, C1 -C4 alkoxy or C1 -C4 haloalkoxy; carbon atoms, Y ¹ is sulfur or NR ²³ , wherein R is hydrogen or (C 1 -C 4) alkyl; then V344 / 94I i 174 R ³ represents a group of the general formula R ²⁴ represents a hydrogen atom, a C 1 -C 4 alkyl group, a benzyl group, a quinolyl group or a phenyl group, R ²⁵ represents hydrogen, halogen, cyano, nitro, C 1 -C 4 alkyl optionally substituted by fluorine and / or chlorine, C 1 -C 4 alkoxy optionally substituted by fluorine and / or chlorine, dioxolanyl or a (C 1 -C 4) alkoxycarbonyl group; and R represents a hydrogen atom, a halogen atom or a (C 1 -C 4) alkyl group; then R is one of the following groups of formulas V344 / 94II 175 A process for the preparation of the sulfonylaminocarbonyltriazolinones of the general formula I according to claim 1, characterized in that the process is carried out (a) reacting the triazolinones of formula (II ') in which: R ¹ and R ² are as defined above with a sulfonyl isocyanates of the formula III ' R ³ -SO ₂ -N = C = O (III) wherein R ³ is as hereinbefore defined optionally in the presence of a solvent, or in the presence of a solvent b) reacting the triazolinone derivatives of the general formula IV in which: 1 2 R and R are as defined above Z represents a chlorine atom, an alkoxy group having a benzyloxy group or a phenoxy group, (IV) to 4 carbon atoms, V344 / 94I1 176 with sulfonic acid amides of formula V R ³ -SO ₂ -NH ₂ (V) wherein R ³ is as defined above, optionally in the presence of an acid binding agent and optionally in the presence of a solvent or a solvent (c) reacting the triazolinones of formula (II ') in which: R ¹ and R ² have the meanings given above, with the sulfonic acid amide derivatives of the general formula VI R ³ -SO ₂ -NH-CO-Z (VI) wherein R ³ is as defined above and Z is as defined above, optionally in the presence of an acid binding agent and optionally in the presence of a solvent, and optionally the compounds of formula (I ') produced by process a), b) or c) are converted into salts. A herbicidal composition, characterized in that it contains at least one sulfonylaminocarbonyltriazolinone of the formula I as active ingredient according to claim 1. V344 / 94II 177 Use of the sulfonylaminocarbonyltriazolinones of the general formula I 'according to claim 1 for controlling undesired plant growth. ' A method for weed control, characterized in that the weed or its locus is treated with sulfonylaminocarbonyltriazolinones of the formula I according to claim 1.