SK280209B6 - Sulfonylaminocarbonyltriazolinones, method for their preparation, herbicidal agents them containing, and their use - Google Patents

Abstract

Compounds of general formula (I) wherein particular substituents are as defined in the Description; a method of their preparation; herbicidal agents containing said compounds; and their use for the control of undesired plants' growth.

Description

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

Certain substituted aminocarbonylimidazolinones, such as 1-isobutylaminocarbonyl-2-imidazolidinone (isocarbamide), are known to have herbicidal properties (see R. Wegler, Chemie der Pilazenschutz- und Schädlingsbekämp-Functionsmittel, 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 provides novel sulfonylaminocarbonyltriazolinones of general formula (I)

R ³ - SO - NE - CO - K i - R ¹ in which

R ¹ is hydrogen, hydroxy, amino, optionally by F, Cl, Br, cyano, C 1 -C 4 alkyl, alkylcarbonyl C 1 -C 4 alkyl or alkoxycarbonyl having 1 to 4 carbon atoms a (C 1 -C 6) alkyl group substituted in the alkoxy moiety each with a fluorine atom, a chlorine atom and / or a bromine atom with a C 3 -C 6 alkenyl group or a C 3 -C 6 alkynyl group or a fluorine atom a bromine atom and / or a (C1-C4) alkyl group substituted by a C3-C6 cycloalkyl group, optionally a fluorine atom, a chlorine atom, a bromine atom, a cyano group, a nitro group, a C1-C4 alkyl group, a trifluoromethyl group, C1 -C4 alkoxy and / or C1 -C4 alkoxycarbonyl C 1 -C 4 alkoxy substituted by C 1 -C 3 phenylalkyl, optionally fluorine, chlorine, bromine, cyano, nitro, C 1 -C 4 alkyl, trifluoromethyl, C 1 alkoxy (C až-C 4), (C-C až), fluoro and / or chloro-substituted (C až-C alko) alkoxy, (C až-C alkyl) alkylthio (C 4-C alkyl), fluoro and / or chloro-substituted (C,-C alkyl) alkylthio (C až-C alkyl) alkylsulfonyl, (C 1 -C 4) alkylsulfonyl and / or (C 1 -C 4) alkoxycarbonyl substituted by a phenyl group, optionally a fluorine atom, a chlorine atom, a cyano group, a phenyl group, a C 1 -C 4 alkoxy group or a 1-alkoxycarbonyl group C 1-4 alkoxy substituted in the alkoxy moiety (C1-C6) alkoxy, (C3-C4) alkenyloxy, optionally fluorine, cyano, (C1-C4) alkoxy or (C1-C4) alkoxycarbonyl substituted by (C1-C4) alkylamino; or C1-C4 dialkylamino in the alkyl moieties,

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, fluoro and / or C 1 -C 3 alkoxy, C 1 -C 4 alkylthio C 1 -C 3 alkylthio, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfonyl, C 1 -C 4 alkylsulfonyl and / or C 1 -C 4 alkoxycarbonyl substituted 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

B ⁵ O

R ⁴ where

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, (C 1 -C 4) alkylthio, (C 1 -C 4) alkylsulfonyl 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

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 alkylsulfonyl, 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 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 2) alkylthio (4) carbon atoms, 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, dialkylamino up to 4 carbon atoms in the alkyl moieties or a group of formula -CO-R ⁸ , wherein R ⁸ represents an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cycloalkoxy group having 3 to 6 carbon atoms, an alkenyloxy group having 3 to 6 C 1 -C 4 alkylthio, C 1 -C 4 alkylamino, C 1 -C 4 alkoxy, C 1 -C 4 alkoxyalkylamino or C 1 -C 4 dialkylamino which are 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 < ⁹ > is optionally fluorine, chlorine, cyano, carboxy, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfonyl or C1-C4alkylsulfonyl; up to 6 carbon atoms; an optionally 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, alkylsulfonylamino. A phenylsulfonylamino group optionally substituted by a fluorine, chlorine, bromine or methyl group;

R ³ is furthermore a group of the general formula

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, which is optionally sub-3

Fluorine and / or chlorine substituted, C 1 -C 4 alkoxy optionally substituted by fluorine and / or chlorine, carboxy, C 1 -C 4 alkoxycarbonyl, dimethylaminocarbonyl, C 1 -C 4 alkylsulfonyl carbon atoms or a (C 1 -C 4) dialkylaminosulfonyl group;

R ³ is furthermore a group of the general formula

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 1-4 carbon atoms optionally substituted by fluorine and / or chlorine;

R ³ represents a group of the general formula

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 alkylsulfonyl 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 C 1 -C 4 alkyl optionally substituted by fluorine and / or chlorine further denotes C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfonyl 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 general formula a ¹ 'FF 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 alkoxy C 1 -C 4 alkyl optionally substituted by fluorine and / or chlorine, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfonyl or C 1 -C 4 alkylsulfonyl optionally substituted by fluorine and / or chlorine , a (C 1 -C 4) dialkylaminosulfonyl group, a (C 1 -C 4) alkoxycarbonyl group or a dimethylaminocarbonyl group, and A represents oxygen, sulfur or 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 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

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 ²⁶

R ²⁴ where

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

and salts thereof.

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 (H) o;

in which

R ¹ and R ² are as defined above with the sulfonyl isocyanates of the general formula (1 H) R ³ -SO ₂ -N = C = O (III) in which:

R ³ is as defined above, optionally 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, C 1 -C 4 alkoxy, benzyloxy or phenoxy, with sulfonic acid amides of formula (V)

R ³ SO ₂ - NH ₂ (V) in which

R ³ is as defined above, optionally in the presence of an acid-binding agent and optionally in the presence of a solvent;

(c) reacting the triazolinones of general formula (Π) o

in which

R ¹ and R ² are as defined above, with the sulfonic acid amide derivatives of the general formula (VI)

R ³ - SO ₂ - NH - CO - Z (VI) in which

R ³ has the abovementioned meaning 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 formula (I) and their salts are characterized by strong herbicidal activity. Surprisingly, the novel compounds of formula (I) have a significantly better herbicidal action than the structurally similar known herbicide 1-isobutylaminocarbonyl-2-imidazolidinone (isocarbamide).

Particularly preferred are compounds of formula (I) in which

R ^{@ 1} represents a hydrogen atom, optionally fluorine, chlorine, bromine, cyano, methoxy or ethoxy substituted alkyl having 1 to 4 carbon atoms, alkyl, cycloalkyl having 3 to 6 carbon atoms, phenyl, benzyl, alkoxy having 1 to 4 carbon atoms C 3, C 1 -C 3 alkylamino or C 1 -C 2 dialkylamino 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 alkylsulfonyl, C 1 -C 3 alkylsulfonyl, up to 3 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

R ¹⁰ where

R ¹⁰ is hydrogen,

R ¹¹ represents fluoro, chloro, bromo, methyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylsulfonyl or dimethylaminosulfonyl and

R ¹² represents a hydrogen atom;

then

R ³ represents a group of the general formula

Table 1 - continued

R ¹ R ²

R ³

O-CH ₂ -CH = CH ₂

^C 2 ^H 5 where

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

HO

R is C 1 -C 4 alkyl.

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

CK ₃ C ₂ H ₅

c ₂ h ₅

Table 1

Examples of compounds of formula (I) R ¹ R ²

ch ₂ -ch = ch ₂ ^C 2 ^H 5 and ₃ ^C 3 * 7

R ³

F

N _{(CH3) 2}

NH-CH ₃ CH ₃

SK 280209 Β6

Table 1 - continued

R ¹ R ²

R ³

Table 1 R ¹ continued

R ²

och ₃

OC ₂ H ₅

^C 2 5 5 ^C 2 ^H 5

R ³

SK 280209 Β6

Table 1 - continued R ¹

R ²

R ³

Table 1 - continued

R 'R ²

R ³ 'Ä ca ₃ ch ₃

C ₂ H ₅ c ₂ H ₄ -t> -CK ₃

_CH2-CH = C C4j

CH

cb ₂ -ch = ch ₂ ch ₃

H ^ AOOC

K-CH, / ^J -H /

Cl

CH j

CH

SK 280209 Β6

Table 1 - continued

R ¹ R ²

R ³

Table 1 - continued

R ¹ R ² _C2 h ₅

OCH 2

C3 (CB ₃ ) j ° c ₂ h ₅ c ₂ to ₅

CH

N _{(CH3) 2}

Them?

If, for example, 2,6-di-fluorophenyl 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:

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 according to the invention can be carried out according to the invention. variant b) is represented by the following reaction scheme:

SCH, O

SCH,

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 may be carried out as described in of the invention according to variant c) represented by the following reaction scheme:

The triazolinones used in the 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 (Π).

In the general formula (II), R ^{@ 1} and R @ ² preferably and preferably in particular have the meanings already mentioned above in connection with the description of the compounds of the formula I according to the invention as advantageous or particularly preferred for R ^{@ 1} and R ^{@ 2.} .

Table 2 gives examples of starting materials of formula (II).

Table 2 Examples of starting materials of formula (II) R R ² H H ch ₃ H ^C 2 ^H 5 H ^C 3 ^H 7 H CH _{(CH3) 2} H ^C 4 ^H 9 H CH ₂ CH (CH ₃ ) ₂ H C _{(CH3) 3} H H CH, H C, H ₅ ³ H C ^ H CH _{(CH3) 2} H ^C Ä H CH ₂ CH (CH ₃ ) ₂ H C _{(CH3) 3} chf ₂ H ch ₂ ch ₂ cn H CH ₂ CH ₂ OCH ₃ H H cf ₃ H ch ₂ and ₃ H ch ₂ oc ₂ h ₅ H CH ₂ CH ₂ OCH ₃ ch ₃ CH ₃ ch ₃ c ₂ h ₅ CH ₃ C ₃ ^H 7

Table 2 - continued R ¹ R ² ch ₃ CH _{(CH3) 2} CH ₃ CH _q 4 7 CH ₃ CH ₂ CH (CH ₃ ) ₂ ch ₃ C _{(CH3) 3} c ₂ h ₅ CH ₃ c ₃ h ₇ CH ₃ CH _{(CH3) 2} CH ₃ ^C 4 ^H 9 ch ₃ CH ₂ CH (CH ₃ ) ₂ ch ₃ ^C 2 ^H 5 c ₂ H ₅ ^C 3 ^H 7 C ₃ H7 chf ₂ ^C 3 ^H 7 chf ₂ ch ₃ chf ₂ ^C 2 ^H 5 CH ₃ cf ₃ c ₂ h ₅ cf ₃ CF ₂ CHF ₂ CH ₃ ^C 2 ^H 5 ^C 3 ^H 7 ^C 2 ^H 5 ^C 4 ^H 9 ^C 6 ^H 5 CH ₃ CH? I ² CH CH, \ J CH 2 CH / | ² CH, -CH 1 J ch ₂ CH ₃

Table 2 - continued

Table 2 - continued r ^! R ² ch ₃ - ^U nh ₂ ch ₃ J-CH NHCH ₃ NHCH ^ CH ₃ nhch ₃ ^C 2 ^H 5 NH CH-j ^C 3 ^H 7 N (CH-J) 2 ch ₃ H (CH ₃ ) 2 ^C 2 ^H 5 N (CH-J) 2 ^C 3 ^H 7 och ₃ ch ₃ och ₃ c ₂ h ₅ oc ₂ e ₅ CH ₃ OC ₂ H ₅ ^C 2 ^H 5

o-ch ₂ -ch = ch ₂ ch ₃

0-ch ₂ -ch = ch ₂ c ₂ h ₅

Table 2 - continued R ¹

Table 2 - continuation of R ¹ o-ch ₂ -ch = ch ₂

nu oc ₂ h ₅

O-CH, -CH-CH? Br-I ^ά

br

OCH ^

OCH ₃

_{OCH3 OCH3} 0-CH ₂ -COOCH ₃ N _{(CH3) 2} N _{(CH3) 2}

N _{(CH3) 2} <D

oc ₂ h ₅

^C ₃ ^K 7

_NH-CH3

CH ₂ -O-CH ₃

CH ₂ -O-CH ₃

CH ₃ CH ₂ -O-CH ₃

The starting materials of formula (H) are known and / or can be prepared according to known methods (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; EP-A 294666; EP-A 301946; EP-A 298371; DE-P 3839206 / LeA 26538 of 19/11/1988; DE-P 3916207 / LeA 26849 of 18.05.1989; DE-P 3916208 / LeA 26850 from May 18, 1989, J. Chem Soc., 1970, 26-34; DE-P 3916930 / LeA 26886 of May 24, 1989).

The triazolinones of the general formula (Π) can be obtained, for example, by:

(a) reacting the oxadiazolinones of formula (VII) o;

in which

R ² is defined as above, with aminodcrivátmi formula (VLH)

SK 280209 Β6

H ₂ N - R ¹ (VRI) in which

R ¹ has the stated meaning, optionally in a solvent such as water, at temperatures between 20 DEG C. and 120 DEG C., while the resulting hydrazine derivatives of the formula (IX)

H CO-NH-H ¹

X /

N

I (IX),

N / \ CO ₂ H wherein

R ¹ and R ² have the meanings indicated, are isolated according to conventional methods (cf. examples) and - or optionally also without intermediate isolation - the compounds of formula (LX) 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

β) Amino derivatives of the general formula (VIII)

H ₂ N - R ¹ (VIH) in which

R ¹ has the abovementioned meaning, are reacted with carbonic acid derivatives such as a 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 has the abovementioned meaning 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-P-3 928 662 / LeA 27137 of Aug. 30, 1989 and Examples).

The present invention also relates to novel triazolinones of formula (IIa)

in which

A ¹ is in each case optionally substituted alkyl, alkenyl, cycloalkyl, alkoxy or dialkylamino, 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 groups simultaneously.

The novel triazolinones of formula (IIa) are obtained, for example, by either oxadiazolinones of formula (VIIa)

in which

A ² are as defined above, reacted with amino derivatives of formula (Vma)

H ₂ NA '(Guilt) in which

A ¹ is as defined above, analogously to the procedure described in (a), or amino derivatives of formula (IIIa)

ΙΙ, Ν-Α ¹ (Guilt) in which

A ¹ has the abovementioned meaning, 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) j C-A ² (X), wherein

A ² and R have the meanings indicated, analogously to the procedure described in ad (β) (cf. 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 group with fluoro, chloro, bromo and / or C 1 -C 4 alkyl; 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, fluoro and / or 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 and / 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 C1-C4alkyl, methoxy, ethoxy or cycloalkyl of 3-6 carbon atoms provided that A ¹ and A ^{2 are} not both alkyl groups simultaneously.

Compounds of formulas (VII), (Fairy), (VIII), (VIIIa) and (X) and (Xa), respectively, which are used as starting materials in the preparation of triazolinones of formulas (II) and (IIa) 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 formula (I) are generally defined by formula (III).

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 R ³ .

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-isopropoxycarbonylphenylsulfonylisocyanate, 2-fluoro-, 2-chloro-, 2-difluoromethoxy-, 2-trifluoromethoxy-, 2-methoxycarbonyl- and 2-ethoxycarbonylbenzylsulphonylisocyanate, 2-methoxycarbonyl-3-thienylsulfonylisocyanate l-methylpyrazole-5-ylsulfonylizokyanát.

The sulfonyl isocyanates of the general formula (III) are known and / or can be prepared according to known processes (cf. U.S. Patent Nos. 4,127,405, 4,169,719, 4,371,391; EP-A 7,687. 13,480, 21,641,223). 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 (I) is preferably carried out using solvents. Practically all inert organic solvents are suitable as solvents. These preferably include aliphatic and aromatic, optionally 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 such as 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; , dimethylacetamide and 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.

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), in each case between 1 mol and 3 mol, preferably between 1 and 2 mol, of the triazolinone of the formula (II), a sulphonylisocyanate of the formula (III) is used.

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. The product of formula (I) formed as crystals is 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 (I) according to the invention as being preferred or particularly preferred for R ¹ and R ² and Z being preferably a chlorine atom, a C 1 -C 4 alkoxy group, a benzyloxy group or a phenoxy group, in particular a methoxy group or a phenoxy group.

Possible additives of formula (IV) are compounds of formula (IV), which can be prepared from compounds of formula (II) listed in Table 2, and phosgene, chloroformic acid methyl ester, chloroformic acid benzyl ester, chloroformic acid phenyl ester or diphenyl carbonate.

The starting materials of 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 formula (IV) are obtained, for example, by reacting triazolinones of formula (II)

in which

R ¹ and R ² are as defined, with carbonic acid derivatives of the formula (XI)

Z - CO - Z ¹ (XI) in which:

Z is as defined 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 preparation of the compounds of formula (I) are generally defined by formula (V).

In the formula (V), 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 R ³ .

Examples of starting materials of formula (V) include the following compounds:

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-methoxycarbonyl-, 2-propoxycarbonyl- and 2-isopropoxycarbonylbenzenesulfonamide, 2-fluoro-, 2-chloro-, 2-difluoromethoxy-, 2-trifluoromethoxy-, 2-methoxycarbonyl- and 2-ethoxycarbonylphenylmethanesulfonamide, 2-methoxycarbonyl-

3-thiophenesulfonamide, 4-methoxycarbonyl- and 4-ethoxycarbonyl-1-methylpyrazole-5-sulfonamide.

The sulfonic acid amides of formula (V) are known and / or can be prepared by known methods (cf. U.S. Patent Nos. 4,1 127,405, 4,169,719, 4,371,391; EP-A 7 687, 13 486, 21 641). 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 general formula (I) is preferably carried out using solvents. Suitable solvents here are virtually all inert organic solvents, as mentioned, for example, for process variant a).

All of the acid binding agents typically used for such types of reactions can be used as acid binders in the process of variant b). 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, for example triethylamine, trimethylamine, dimethylaniline, dimethylbenzylanone, pyridine, 1,5-diazabicyclo [4.3.0] non-5-ene (DBN), 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU) a

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 components in greater 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 (I) 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 (I) according to variant c) of the process according to the invention are generally defined by formula (VI).

In formula (VI), the symbols R ³ and Z preferably have, or in particular, those already mentioned in connection with the description of the compounds of the formula (I) according to the invention or with the description of the compounds of the formula (IV). 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 greater 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 (I) are mixed with suitable salting agents, 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 can 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, roripa, Rotala, Lindemia, deadnet (Lainium), veronica (Veronica), abutilon (Abutilon), Emex, durman (Datura), violet (Viola), cannabis (Galeopsis) , poppy (Papaver), neva (Centaurea), clover (Trifolium), Ranunculus, Taraxacum;

dicotyledonous plants of the genera: cotton (Gossypius), soybean (Glycine), beets (Beta), carrots (Daucus), beans (Phaseolus), peas (Pisum), potatoes (Solanum), flax (Linum), tunicate (Ipomoea), Vicia (Vicia), Tobacco (Nicotiana), Tomato (Lycopersicon), Peanut (Arachis), Kohlrabi (Brassica), Salad (Lactuca), Cucumber (Cucumis), Pumpkin (Cucurbita);

monoecious weeds of genera:

hedgehog (Echinochlora), bar (Setaria), millet (Panicum), fingergrass (Digitaria), timothy (Phleum), meadowgrass (Poa), fescue (Festuca), eleusine (Eleusine), Brachiaria, inätonoh (Lolium), stoklas (Bromus) ), oats (Avena), chess (Cyperus), sorghum (Sorghum), wheatgrass (Agropyron), hawk (Cynodon), Monochoria, Fimbristylis, dart (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 sites and on roads and squares, possibly with tree growth. 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 1-year crops.

The compounds of formula (I) according to the invention are suitable for controlling monoecious 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 of the invention also exhibit fungicidal activity, for example against powdery mildew fungi and against apple scabs as well as 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 polymers. 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 dimethyl sulfoxide, 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 granulates are crushed and fractionated natural stone materials such as limestone, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, coconut shell , corn sticks and tobacco stalks. Suitable emulsifiers and / or foaming agents are non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol 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.

In addition, these 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 in their own form or in the corresponding compositions, and final mixing before the actual 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;

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 weed control in soybean; 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),

Chloroacetic acid N- (methoxyniethyl) -2,6-diethylanilide (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 (BEN-

TAZON), methyl 5- (2,4-dichlorophenoxy) -2-nitrobenzoate (BIFENOX),

3,5-dibromo-4-hydroxybenzonitrile (BROMOXYN1L). 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 (CHLORSULFURRON), 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), 2-f (2-chlorophenyl) methyl-11,4-dimethylisoxazolidin-3 -one (DIΜΕΊΉΑΖΟΝΕ),

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),

- 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-dihydromethyl-4- (1-methylethyl) -5-οχο-ο-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- (1H) ) Imidazol-2-yl] -5-ethylpyridine-3-carboxylic acid (ΙΜΑΖΕΊΉΑPYR)

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 (METAZACIILOR),

2-ethyl-6-methyl-N- (1-methyl-2-methoxyethyl) chloroacetanilide (METOLACHLOR), 2 - {[[((4-methoxy-6-methyl-1,3,5-triazin-2-yl)] (amino) -carbonylamino-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) -5-octylthiocarbamate (PYRIDATE), ethyl ester 2- [ 4- (6-chloro-quinoxalin-2-yloxy) -phenoxy] -propionic acid (QUIZA-LOFOPETHYL),

2- [1- (ethoxamino) butylidene] -5- (2-ethylthiopropyl-1,3-cyclohexadione (SETOXYDIM), methyl 2 - {[4,6-dimethyl-2-pyrimidinyl) aminocarbonyl] aninosulfonyl} benzoate (SULFOMETORON) 4-ethylamino-2-tert-butylamino-6-methylthio-sec-triazine (TERBUTRYNE), 3 - [[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl) methyl ester] ) amino] carbonyl] amino] sulfonyl] thiophene-2-carboxylic acid (THIAMETURON)

N, N-diisopropyl-S- (2,3,3-trifluoroallyl) thiolcarbamate (TRIALLATE),

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

Surprisingly, some compositions also have 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 compounds can be applied per se, in the form of concentrates or dosage forms prepared from such concentrates, 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.

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.

DETAILED DESCRIPTION OF THE INVENTION

(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 the resulting solution is stirred with stirring. 6.9 g (28.6 mmol) of 2-methoxycarbonylphenylsulfonylisocyanate dissolved in 20 ml of acetonitrile are added. 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-methoxycarbonylphenylsulphonylaminocarbonyl) -2,4-dihydro-3I-1,2,4-triazol-3-one are obtained. C.

(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-carboxylic acid with stirring. methyl 2-phenoxycarbonyl-2,4-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-triazole-3 are obtained. -one having a melting point of 176 ° C.

Analogously to Examples 1 and 2 as well as in accordance with the general description of the production processes of the invention, the compounds (I) listed in the following Table 3 can also be prepared:

¹ - Sat ₂

(I)

Table 3

Examples of prepared compounds of formula (I) Example R * R ² R ³

No.

Melting point (° C)

Table 3 - continued

Example R * R ² R ³ Melting point

no. cc)

c _& h ₅ ca ₃

153

COOCH}

C ₂ K ₅

159

115

CH ₃ C ₃ H ₇

143

c ₂ h ₅

Table 3 - continued

Example R ^R R ²

no.

R ³ Melting point (° C)

Table 3 - continued

Example R * R ²

no.

R ³

Melting point (° C)

3B

n, _{CH3> 2} hícHj> ₂

COOCH

^ Jj thereof

N (CH ₃ > ₂ ch ₃ ^C 3 ^H 7)

OCH,

CH 3 c ₂ h ₅ ^C 3 ^K 7

CH _{(CH3) 2}

C ₄ H ₉

C ₄ H 8 H 9

Cl

CH-) _f coocK ₃

COOCHj

COOCHj

J-COOCH

J-COOCH

Cooch

COOCH,

COOCH, '

146

110

131 se

113

B8

117

11?

141

130

139

151

CHj CjJLj

OCF, d-

-ch ₂ ce = ch ₂ c ₂ h ₅

-CH ₂ CH = CH ₂ H

195

158

110 - Hl

212-214

160-165

SK 280209 Β6

Table 3 - continued

Example R ^f R ²

no.

R ³ Melting point (° C)

Table 3 - continued

Example R ^R R ²

No.

R ³ Melting point (° C) c ₃ h ₇

57 OCH c ₂ h ₅ 58 - OCH. .

6c, _-CH2 -CH _{2 CH}

Ο.Η - Π j 7 ch ₃

C ₃ H ₇ -n

-CH ₂ CH (CH ₃ ) ₂ c ₂ h ₅

-CH ₂ -CH = CH ₂

196

173

177

123 (• Norwegian / product ’

J-COOCH

COOCH.

• J

133

157

-C _{(CH3) 3} C ₂ S ₅

117

1o2

133

-OCH _q

CK (CH _{3) 2}

CH ₃

COOCH.

/ ³

F

196

153

133

191

191

192

L

110

152

174

SK 280209 Β6

Table 3 - continued

Example R ^f R ² R ³

no.

Melting point (° C)

Table 3 - continued

Example R ^f R ²

C.

R ³ Melting point (° C)

Bl CHj

(aoori'ny before what)

- ° c ₂ ^hours ₅ c ₂ hours ₅

Table 3 - continued

Example R ^f R ² R ^3/1

Melting point (° C)

SK 280209 Β6

Table 3 - continued Example R ¹ R ² no. R ³ Melting point (° C) 136 C 11 (CH ₃ ) ₂ C ₂ H _; C! gl · -2 13 7 c: -: ₃ chic: -: ₃ > ₂ C L 125 13 S c ₂ h ₅ CC {CH ₃ » ₂ dp 250 : 3 9 C ₃ r ₇ -n (CHCl ₃ ); d- 255 140 CH (CH ₃ ) ₂ ch ₃ C00Cr.- | -WITH  hl c ₃ K ₇ - _n C ··. C0CCH-, ζ y. 130 1 * 2 c ₃ : -: ₇ -nc _of h ₅ cocc: - \ about 1S 7 1 * 3 ch (ch ₃ ) ₂ c ₂ h ₅ COOCH-. gl · 133 CCOC? -, value is higher c: -: ₃ c ₃ H ₇ -n about 2 S N • i) C, H; C ₃ H ₇ -. CCCCFS Gl · ' L7 2 C00CH- » 1 L z c -: -: ₇ c ₃ H ₇ -r. gl · 14 3 COOCHg 147 ch (c: -: ₃ > ₂ c ₃ H ₇ -n about  23 Cooc: -: ₃ 1 * 3 ch ₃ c: -: <c: -: ₃ > ₂ dZ / ~ 1 / 1 * 9 c ₂ : -: ₅ CH (CH ₃ > ₂ COOCr. Cl · ' '27 150 C ₃ H ₇ -n CH (CH ₃ ) ₂ COOCH- gl · about 151 ch (c: -: ₃ i ₂ ch (CH ₃ > ₂ COOC: -: - i Cl · L 67

Table 3 - continued Melting point (° C) Example # l R ¹ R ² R ³ 152 CH ₂ ^c 2 ^h 5 CGCCH-j d- 144 COCCHn 153 C H η CH j cl · I-I * 15 ΟρΗς CH ₃ COOCH, Cl · 14 CC0CH-. 155 <3 C H T cl · 156 CC  . CH, COCCH-> Cl · 17- COOCH, . 157 158 -NCCHjl 2 ^CH 3 dS C00CH- » Cl · qc ₂ h ₅ 183 159 Cn ₃ Cn ₃ dd 190 160 CH ₃ oc ₃ h ₇ , COOC ^ ____ r. ΙΓΊΓ $ d- 120 ch ₃ 161 ch ₃ 0 C 2 · “7 d- 1 34 162 CH ₃ ^0C 2 ^K 7 ar Cl · 122 163 Cr: ₃ Oc ₃ h ₇ cogc ₃ h ₇ cl · 1 25 * 16 c: -: ₃ oc ₂ h ₅ —— SOCCO 2 Ecid ^{2 5} 166-167 ch ₃ 165 CH Cc ₂ h ₅ COOC rl · 131-132 166 ch ₃ oc ₂ h ₅ cl · 147-148 167 ch ₃ 0C ₂ H ₅ 3r Cl · 186-187 L68 ch ₃ oc ₂ h. ₅ COOC-5H7 cl · 125-126 169 ch ₃ oc ₂ h ₅ C00C ₇ H _with Cl · 123-124

SK 280209 Β6

Table 3 - continued Example R * R ² R ³ Melting point No. (° C)

Cl

170 0C ₂ .H ₅ 0 1 as-: e? 17 1 oc ₂ h ₅ . Cl o ch ₃ 17S-17? 172 c: - ₃ oc ₂ : -: _p 0C ~ t 0 15 - 152 173 ch ₃ oc ₂ h ₅ C5 172-173 17i ch ₃ oc ₂ h ₅ OCH.-> 147-143 175 ch ₃ oc ₂ h _p Cl C 13 and 34 Cl 176 ch ₃ OCjHj [ΓϊΓ ^X 'S < ^z ^ COOCH3 173-133 177 Ch ' ₃ oc ₂ h ₅ ocr ₃ 155-156

l SO From ₂ y, ₇ y 0Cn ₃ COOCF-3 <Ζλ 129 * 120 ίδ ' C ₃ n _? OCH 3 ï L SO- 15 i 6r 132 ^C 3 ^h 7 0Cr: ₃ EN - / * ^- '30 -131 'IS3 ^C 3 ^K 7 qch ₃ C00C-> H ₇ 0 135-136 18i ^C 3 ^?; 7 qch ₃ CCCC ₇ Ke α 126-127 135 c ₃ h ₇ OCH 3 C L a 116-117 185 C ^ 7 a-3 1 ____ ^ cacc ₂ 5: ₅ 12-9-130 '3: c ₃ : -: ₇ OCH c: -: ₃ cl 156-157 CH

Table 3 - continued

Example # R ^r R ² R ³ Melting point (° C) C -, - l ₇ Oh. OCr 0 -7- ! ia l «9 CjH _t OCH Ο ^- 13? · 190 c ₃ : -: _l 0Cn ₃ □ CHF. 0 115- 1! with 191 ⁼ 3 ^K 7 CCHj CL 153- 184 192 ^C 3 ^K 7 och ₃ Cl ICC. 130 · -131 193 c ₃ h ₇ OCH-j OCF-i CK 106 -107 19 ' ^C 3 ^K 7 OCH cxx 122 · • 123 L 9.5 c ₃ h ₇ och ₃ Ο ^- 125 • .z J I9ó CH oc.x. COOCH, Fr. 70 19? c ~. 0C, H, , ----- ^ COOC, Tς tfl ^{2 5} I? 7 193 c: -: -, OC; · - :, CK ₃ H- 15 3 199 CH, 0 ^C <“9 CDCl 3, H ₇₀ 0 105 200 0 ^c <9 COOCpHc 0 81 201 CRIJ oc ₄ h, OCà _n 0 137 20 3 CH 0 '< ^H 9 0 t3

Table 3 - cont'd Example R ^R R ² no. R ³ Melting point (° C) ^{210 en} 3 »O ocr. D l? l C'3 ^0H H D 20 7 212 TA ₃ 3 ï 1 5 4 213 CH. OCH! ï CH. CCH ₃ D 17? 2 t 5 -ch ₂ -c: -: ch ₂ and ₃ COOCH-i d ' 1 2 <4 216 - CH 2 CH ₂ CH ₂ OCH. Q CK ₃ 153 2L7 -c: -: ₂ -ch ₂ and ₃ Br d 150 213 -CE ₂ -CH'CH. Oh. ï  03 219 -ch ₂ -ch; c: - ;, -oc. ··: - Cr 120 21 '· ch ₅ cc; D :, ₄ 221 c.- :, OCH. Ccocha. ABOUT 125 c ;. _{! z} -c-. _: g-. ₂ och- CCOC.-.-. ABOUT ' 130 D 211 θθ COOC.He about- 17? 2'5 _CH3 OCKj DCHr, d 171 226 -CH ₂ -CH ₂ -CH ₂ CCH- in-3 "> G CCHr, d 5 2 c: -; _{5 c 3} n ₇ Ccocha. D u. 22- CHj GCHj coqc -.-: ₇ 14 3 ° ~ O cT 23; '-No _CH2 -. Cr: ₂ ° C _Hj COOC.H. D ! 35 GCH. d ^ 148 OCH _: D 150

Table 3 - continued Example # R ¹ R ² R ³ Melting point (° C) 23i -Chg-CH'Cr-j och ₅ D J 2S 235 c: -: -. OCH-j 0CF-i d L 4 5 236 c,: -: _p OCH CQ-> CH-> rG S_z l53-1S 4 23 ' c ₂ h '_; Oh, D LSL-152 233 c ₂ h ₅ Oh. D r d 167-158 239 ^C 2 ^H S OCH-j D 1SS-1So 240 C ₂ n; och ₃ cr 174-175 241 ^L 2 ^h 5 OCH-j C.-. 3 rT ^c3zCi 140 “14 i 242 c ₂ h ₅ CC H ₃ 1 ch ₃ co ₂ c ₂ h ₅ d 160 243 C, H _S CCN ^ ocs ď 146-14 ' 24i c ₂ h _p 0c: -: ₃ ï S 5 š - 1 57 245 C, H _S 0ra ₃ gF 1 25-125 246 c ₂ y: ₅ OCH 0C. ~ ₅ Gd 137-136 247 c ₂ h ₅ OCH ₃ d- 203-204 248 ch ₃ ° c ₄ h, Cl d 1 18-119 249 ^C »3 oc ₄ h, Cl d 146-147 250 ch ₃ oc ₅ h, C L ABOUT 110 - '. ·' 251 C h ₃ 0C, H, CH OC *. Cd- 123-124 2 52 cc _of h ₅ d- 152-153

SK 280209 Β6

Table 3 - continued

Example R ^f

Melting point

codc _2. · p

cooc ₃ h ₇

Table 3 - continued

Example RR ²

No.

273

75

Cr (Cr 2> 2)

277

278

279

2SC per i

282 • C'r. <Cr: ₃ ' ₂ cKtCr :-) ₂

CKICE ^ j

CŕHCH _{3) 2}

Cr. _(Cr.: L ₂

CH 2 CH 2 C ₂ h ₅

CC ₂ He oc ₂ ?. ₅

0C ₂ H _s oc ₂ e _s oc ₂ h ₅ cc ₂ h ₅ oc ₂ E _s

OCH ₃

285 -icr: _2: , -oc: -: ₃ and ₃ 286 - '' -? ₃ -och ₃ C: -: ₃ 28 ' - (CH ₂ i-OC ₃ - ₃ 0CH ₃ 2ea - <CH _{2 13} -och ₃ and ₃ 7S9 -ich ₂ i , OCH ₃ 0CK ₃ 290 - (ch ₂ > J-OCH-jOCH ₃ 7 0 i. ^(CK 2 > .- och ₃ och ₃

R ³ Melting point (° C)

COOCH-.

COOC ₂ r ₅

Cr.-j

210-231

Table 3 - continued R ³ Melting point (° C) Example # R ¹ R ² 2G7 - ^c 3-7 oc ₂ h < CCCCHj about- i os 293 --c, h ₇ oc ₂ h ₅ [_____ ^ ccoc _of H _s ' IC ch ₃ 2'2-213 294 nC _{3 -} : ₇ OCyHg d- 106-10 295 nC ₃ Kj 0C ₂ H ₅ cf 127-123 296 ^{n C} 3 ^H 7 OC ₂ H _p CGCC, He <F 9S 297 oc ₂ - _ä Cl Cl · i 32 i 35 298 oc ₂ : -: _p C l o CH, 138-140 299 nCr. ₇ ^0c 2 ^H 5 OC ", 7 £ £ S 300 nC ₂ H ₇ oc ₂ h ₅ · cl ' ioô ·; cs 301 n-C, _H7 0¾ D 154-157 302 nC ₃ H ₇ »C ₂ : -: _p CH -, - Cl · 130-133 303 CH _{(CH3) 2} och ₃ COOCH, Cl · ' 1S0-1SI 304 CK (CH-) ₂ OCH 3 cooc ₂ h _p 160-161 1 ch ₃ 305 CW (CH-) _Z OCH <d l ··· “- iq 30o Ch (CH3) ₂ OCH <d 14 N -1 5 0 30i <* <0ί,> ϊ OCH cl · ^ ⁵ 14 3 - i <4 305 ch (c: -: ₂ ) ₂ OCH <d 309 c: 3 <c: -: ₃ 3 Oh, <d CH, 147-150 310 Chick ^ Oh, cl · ³ 146-150 311 CH _{(CH3) 2} OCH cl · ³ 14 J - 14 S 312 CH _{(CH3) 2} OCH 3 cT 114-116

Table 3 - continued R ³ Melting point (° C) Example R ¹ no. R ^x 313 (Cr ₃ > ₂ 0c: -: ₃ , CK ₃ o- 25 - L 2S 3U CH 3 0CH (CH _{3) 2} COOCH, Cl · ' ? S -57 3 l 5 CH 3 Oh (ch,) ₂ cl · 15 3-! © O 316 CH 3 OCK _(CH3) j COOC-JHE cl · 53 317 ch _{3 2)} OC "-. cl · 1S0-152 31 é ch ₃ 0Cn (CH _{3) 2} d- ³ ise-130 319 ch ₃ 0CH (CH _{3) 2} CH, Cl · ' L E 0 - 1 E 2 320 ch ₃ ° <] COOCH, Cl · 117-118 3 2 L CH, "C. • / ^K 3 cl · 30 - L 32 322 C ° c ₂ : -: ₄ rT ^ S ^ COOC K8-150 h ₃ 323 ^C 2 ^H 5 och ₃ [Γ "ϊΓ 172-173 3 2'- -ch ₂ -ch-ch 3 ⁰ E ^{N K} 5 CO ^ j- ^ COOC! 130- 32 325 ch (c: -: ₃ ); oc ₂ h ₃ ΓΤ ^ 'P - ^' nsooc · «·« 326 - (c: -: ₂ ) _2- night R ₂ 0CH ₃ FT ^ S ^^ COOC " 127-130 '3 • 327 ^ -c ₃ h ₇ ^0c 2 ^h: p FT ^X _p - ^x ^ 'cccc: · 127-130 b 328 CH ₂ CH ₂₎ OCH ₃ F ~ F ^ 5 ^ --- 3033 - 156-157 329 * 3 OCr (CH 1 12 ₎ OI ^ P - ^^ cccc: - 155-200 • 3 330 CK (CH ₃ ) _z 0C ₂ H _p COOC, b Cl · : ₇ -n 122-124 3 3 Ľ <CS ₂ l ₃ -OC.- ₃ oc: ^ ₃ ccoc, h ₇ cl · " 97 -9S 332 n -c ₃ h ₇ ° C ₂ H ₅ COCC-H, - Cl · 128-130 333 C : h <ch, i ₂ OCH ₃ cgoc, h ₇ - a 146-150 334 C -3 Ochichi,) j CCCC, to-- Cl · • 54

Table 3 - continued Example R ^r no. R ² 335 c ₂ h _p 336 ^0C 2 ^H δ 337 oc ₂ h ₅ 338 ch ₃ OC ₄ H ₉ -n 339 CC H 3 3 ^ 0 -> CH ₂ -ch ₂ -c- 1 oc ₂ h ₅ 2Δ7 c: -: ₂ ° ^c 2 ^ 5 3 ^ 3 ^CH 3 oc: -: ₃ 3ώΑ CH ₃ "ABOUT 3 ^ 5 and ₃ oc ₃ h ₇ 3-6 CH ₃ 0CH3

R ³ Melting point (° C) cooc ₂ r: ₇ -T

G> Stage 2:

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 is adjusted to 3-4 by addition of concentrated hydrochloric acid and the mixture is concentrated. The residue was triturated with ethyl acetate and the sodium chloride remaining undissolved was filtered off. 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 of melting point 93 DEG C. are obtained.

Example (II-2)

GV o

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 CH3NH2) and 500 ml of water is heated under reflux for 12 hours. condenser and then 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 of melting point 86 DEG C. are obtained.

Example (II-3) o

Starting materials of general formula (Π):

Example (Π-1) 11 HN - 0C _? . <I 1 N ------ L c ₂ H ₅ Stage 1: nn-co-nh-oc ₂ h ₅ H - N - CO - C ₂ H ₅ (LV-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.

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, then the mixture is heated slowly and stirred for 4 hours. at 60 ° C.

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 methanol formed by distillation, phenol is 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 of melting point 127 DEG C. are obtained.

SK 280209 Β6

For example, the compounds of formulas (II) and (IIa) shown in Table 4 below can also be prepared in an analogous manner to those described in Examples (H-1) to (L-3).

Table 4 - continued

Example # R ¹ R ² Melting point (° C)

130

154

Table 4

Examples of prepared compounds of formula (II)

Example # R ¹ R ² Melting point (° C)

11-37 K (CH3) ₂

11-38 N _{(CH3) 2}

II-3 $ N (CH-) ₂

ΪΙ-4Ο MtCH-j),

71-41

II-4 ^C 3 ^H 7 CH 48 II-5 CH (CH) 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 11-9 CH (CH ₃ ) 2 c ₂ h ₅ 102 11-10 ^C 2 ^H 5 CjFÍ. 97 II-U CJH. (eaorphic product 11-12 CHtCHjl '2 c ₃ h _? 51 II-IJ J-CH CH (CK ₃ ) ₂ 92 11-14 c ₂ h ₅ ch (ch ₃ ) ₂ faoorphic product) 11-15 c ₃ h ₇ CH _{(CH3) 2} (amorphous product) 11-16 CH (CH ₃ h CHCl ₂ 168 1I-L7 c ₂ h ₅ CH ₃ 134 CH. 159 11-19 OCH-j J-CH 178 11-20 OCH-j c ₂ h ₅ 140 11-21 OCH ^ ^C J ^H 7 127 11-22 OCH-j CH _{(CH3) 2} 130 11-23 och ₂ c _s h ₅ ch ₃ 106 II- 24 ^C 2 ^H 5 15C 11-25 C-.mu.L, 130 II- 26 ^OC 2 ^K 5 ^C 3 «7 72 I-I-27 CH _{(CH3) 2} 121 II- 28 CHt c ₄ h ₉ 50 II- 29 c ₂ to ₅ in ₅ 76 11-30 <3 _Λ ^C Ä (aoorphia) and product) II- 31 ^0CH 3 c ₄ h, 100 11-32 ^C A 66 11-33 J-CH 66

11-42

11-43

11-44

11-45

IT-46 hp (cm p ₂₎

CK (CH ₃ ) N (cnp ₂ c ₂ h ₅₎

C _{(CH3) 2}

N _{(CH3) 2}

ch ₃

153

114

1CS

100 so

134

205

145

11-49 CCH, Π-50 ch ₃ 11-51 hh ₂ 11-52 ^NH 2 11-53 nh ₂ 11-54 NHCHj 11-55 NHCK-j 11-56 nh ₂ 11-57 nh ₂ II- 58 KHCH} 11-59 CK ^ H. 11-60 NHCH. j II-6I HHCH ₃ 11-62 NHCM-j 11-63 NH.

11-64 M?

11-65 NH ₂

11-66 NH ₂

176

183

210

Table 4 - continued R ² Melting point (° C) Example # R ¹ 11-67 nhch ₃ c ₂ h ₅ 101 11-68 UK ₂ H (C 3 H ₅ ) ₂ 196 11-59 NH ₂ N- 233 11-70 nh ₂ ch (ch ₃ : ₂ 172 11-71 nh ₂ C (CH-j) j 261 11-72 ^NK Z CK ₂ CH ₂ OCH ₃ 98 11-73 nh ₂ C (CK ₃ ) ₂ C ₂ H ₅ 213 ΙΓ-74 nh ₂ nhc ₃ h ₅ 220 11-75 nh ₂ OCH-j (amoríay produkt) 11-76 nh ₂ CR & CCE. 134 11-77 nh ₂ CH ₂ OC ₂ H ₅ 104 11-78 R (CH _{3) 2} ^CH 3 153 11-79 -ch ₂ , Z 1 c ₂ h ₅ 105 11-80 -CH ₂ CH (CH ₃ ) ₂ ^c 2 «5 105 ΙΙ-Θ1 ^c 6 ^H 5 H 1Θ3 11-82 H (CE-j) ₂ CH (CH ₃ > ₂ (eoorphic product) ΙΙ-Θ3 nhch ₃ ch ₃ 114 11-84 hh ₂ ch ₂ c ₆ h ₅ 168 11-85 NH ₂ N _{(CH3) 2} 207 11-86 ^C 6 ^H 5 230

Table 4 - continued

Example # R ¹

11-99 -CH 3 CH = CH ₂

II-IOO c ₆ H ₅

R ² Melting point (° C) c ₂ h ₅ 132 ch ₃

108

150

116

146

105

194

11-87 KE,

11-88 NH ₂

Π-89 KHCH ₂

NHCH (CH-J) ₂ nhcm _{(CH3) 2}

3

152

120

11-107 C [CH ₃ ] ₃ h

IOE-11 -CH ₂ -CH-CH ₂ Br Br CH ₃ 111 11-109 CH ₃ -CH ₂ OCH ₃ 104 Π-110 ^CH 3 -CR ₂ OC ₂ H ₅ 102

11-91 --- N _{(CH3) 2}

51-92 ^C W ₅ H 111 11-93 c ₃ h ₇ M 4Θ 11-94 ^C 6 ^H 5 c ₂ h ₅ 124 ir-95 C _{(CH3) 3} c ₂ h ₅ 150 II-9S ^CH i H 157 11-97 c ₂ h ₅ lot

-CH_OC_H_ 2 2?

119

H (CH _{3) 2} ^l 3 ^q

11-114 KH ₂

-N x

c ₂ h ₅

II-115 Na ₂ / ^CH 3 -N \

CYY n

186

SK 280209 Β6

Table 4 - continued

Example # R ¹

R ² Melting point (° C). ^C 2 ^K 5

-N

186

117

-K

11-118 CH-j

C ₃ H _? -n

267

-OCH

144

Table 5 - continued

Example. R ¹ R ² Melting point (° C)

IX-10 OCH ₃ C ₄ H ₉ 134 ix- _11-15S

IX-12 ιββ

IX-13 OCH 140 IX-14 ch ₂ -ch = ch ₂ c ₃ h ₇ 13 '! IX-15 -CHjOCjK ^ 97

The compound shown in Table 4 as an example (11-118) can also be produced, for example, as follows:

about

OCH

50.2 g (0.33 mol) of hydrazinic acid phenyl ester and 3 .mu.g ((0.33 mol); 90%) of 0,0, N-trimethyliminocarbonate are mixed at 100C with 100 ml of o-dichlorobenzene 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 residual volatiles (methanol, phenol and o-dichlorobenzene). Above 120 ° C, no product distilled in the crude state and this was 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 the step of example (II-1).

HN - CO-NH-R ¹

^HN-CO-R2 (IX)

Starting materials of formula (IV)

Example (lV-1) o

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.

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.

For example, the compounds of formula (IV) listed in Table 6 below can also be prepared in an analogous manner to that described in Example (IV-1).

Table 5

Examples of hydrazine derivatives of formula (IX) Example # R ¹ R Melting point (° C) IX-2 OCH c ₂ h ₅ 120 IX-3 OCH _} 125 IX-4 OCH CM (CH3) ₂ 127 IX-5 CH ₃ 100 IX-6 - c ₂ h ₅ 174 IX-7 CJR, 180 IX-E OC ₂ H ₅ C, H, 119 IX-9 CH (CH ₂ ) ₂ 150

about

Table 6

Examples of compounds of formula (IV) Example # R ¹ R ² FROM Melting point (° C) IV-2 c ₃ h ₇ g ₃ h ₇ ^C 6 ^H 5 the IV-3 OCH ^C 3 ^: 7 ° 5 ^H 5 82 IV-4 CH 5Y ^C 6 ^H 5 84 IV-5 nh ₂ ^C 3 ^H 7 ^C 6 ^H 5 133 IV-6 NH _? CH ^C 6 ^H 5 82 IV-7 = ₂ h ₅ ^C 6 ^K 5 152 IV-8 OC ₂ H ₅ c ₂ h ₅ ^C 6 «5

SK 280209 Β6 (1)

Table 6 - continued Melting point (° C) Example # R R ^z FROM IV-9 and ₂ ch = ch ₂ ^ch 3 ^C 6 ^H 5 IV-10 Φ ^C 4 ^H 9 ^C 6 ^H 5 IV-11 IV-12 CH-i-n- ₃ ^c 2 ^h 5 ^C 6 ^h 5 IV-13 CH ch ₂ c ₆ h ₅ ^C 6 ^h 5 IV-14 UHCH (CH _{3) 2} ^c 6 ^h ₅ IV-15 N _{(CH3) 2} N _{(CH3) 2} ^C 6 ^H 5 IV-16 ^C 6 «5 Π-17 oc ₂ and ₅ ^C 6 ^H 5 IV-18 OCýl ₇ ^C 2 ^H 5 ^C 6 ^K 5 TV-19 c ₂ H ₅ ^C 4 ^H 9 ^C 6 ^and 5 IV-20 CH _{(CH3) 2} CH _{(CH3) 2} ^C 6 «5 IV-21 OCH-j ^C 2 ^H 5 ^C 6 ^H 5 69 IV-22 5Y ^C 6 ^K 5 104

ci

about

(7) (8)

Application examples

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

™ N-CO-NH-CH ₂ CH (CH ₃ ) (A)

Y o

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):

(14) (14)

(17)

SK 280209 Β6

(20) (26) (27) (18) (19)

(33) (34) (35) (37) (39) (40) (9) (31) (36)

SK 280209 Β6

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 have a significant superiority over the prior art in this assay.

Example B

Postemergence test Solvent: 5 parts by weight acetone Emulsifier: 1 part by weight 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, the said amount of emulsifier is added, and the 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 untreated control plants)

100% = complete destruction of plants

In this test, for example, the compounds of the Examples of Embodiment No. 1 exhibit a significant advantage over the prior art. 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

Pyricularia oryzae (iyza) test / protective action 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.

To test for 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.

days after inoculation, the disease is evaluated.

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

Example D

Pyricularia oryzae (rice) / systemic effect test Solvent: 12.5 parts by weight acetone Emulsifier: 0.3 parts by weight 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 the stated 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.

For example, compounds of the following Examples have excellent activity in this test: 9, 12, 13, 20, 30,31,32, 33,34,35, 36 and 37.

The results of the tests described are shown in Tables A to D.

Table A: Pre-emergence test / greenhouse

Active substance Application rate (g / ha) Setaria Chenopodium Matri čaria Purslane Solanum (A) 500 0 50 0 40 0 (6) 250 100 80 95 70 90 (2) 250 100 70 100 90 80 (8) 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 90 100 100 (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

(29) The 250 95 80 90 90 95 (34) 250 100 90 100 90 QT) 125 95 80 70 50 90 (39) 125 90 70 80 80 90 (40) 250 100 95 90 100 95

Table B: Post-emergence test / greenhouse

Active substance Application rate (g / ha) Amaranthus Datura Galinsoga sinapis Solanum (A) 1000 0 10 60 20 0 (4) 125 100 90 95 95 95 (5) 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 (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 (19) 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) The 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 (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 (A) 1000 0 10 60 20 0 (4) 125 100 90 95 95 95 (5) 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 (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 (19) 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) The 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 (34) 250 90 80 90 100 95

SK 280209 Β6

Active substance Application rate (g / ha) Amaranthus Datura Galinsoga sinapis Solanum (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 C: Pyricularia-test (rice) / protective

The active substance according to Ex. no. active substance concentration in% degree of effect in% of untreated 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

Table D: Pyricularia-test (rice) / systemic

The active substance according to Ex. no. Application rate in mg of active substance per 100 cm ² degree of effect in% of untreated 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

PATENT CLAIMS

Claims (5)

PATENT CLAIMS Sulfonylaminocarbonyltriazolines of general formula (I) o in which R ¹ is hydrogen, hydroxy, amino, optionally fluorine, chlorine, bromine, cyano, C 1 -C 4 alkoxy, C 1 -C 4 alkylcarbonyl or C 1 -C 4 alkoxycarbonyl a (C 1 -C 6) alkyl group substituted in the alkoxy moiety, in each case by a fluorine atom, a chlorine atom and / or a bromine atom, a C 3 -C 6 alkenyl group or a C 3 -C 6 alkenyl group or a fluorine atom chlorine, bromine and / or C 1 -C 4 alkyl substituted C 3 -C 6 cycloalkyl, optionally fluorine, chlorine, bromine, cyano, nitro, C 1 -C 4 alkyl, trifluoromethyl , C1-C4alkoxy and / or alkoxycarbonyl C 1 -C 4 alkoxy substituted by C 1 -C 3 phenylalkyl, optionally fluorine, chlorine, bromine, cyano, nitro, C 1 -C 4 alkyl, trifluoromethyl, alkoxy (C 1 -C 4), fluoro or α / chloro-substituted by C 1 -C 3 alkoxy, (C 1 -C 4) alkylthio, C (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 substituted in the alkoxy moiety 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 fluorine, cyano, (C 1 -C 4) alkoxy or (C 1 -C 4) alkoxycarbonyl substituted by C 1 -C 4 alkoxy 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 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, fluoro and / or C 1 -C 3 alkoxy, C 1 -C 4 alkylthio C 1 -C 3 alkylthio, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfonyl, C 1 -C 4 alkylsulfonyl and / or C 1 -C 4 alkoxycarbonyl substituted 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 D 5 O '· / where 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, dialkyls a C 1 -C 4 nosulfonyl group in the alkyl moieties, a C 3 -C 6 cycloalkyl group 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, (C 1 -C 4) alkylthio, (C 1 -C 4) alkylsulfonyl 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 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 up to 4 carbon atoms in the alkyl moieties, phenyl or -NHOR '; 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 alkylsulfonyl, 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 alkyl moieties; (C 3 -C 6) alkenyl optionally substituted by fluorine, chlorine or bromine; (C 3 -C 6) alkynyl, (C 3 -C 6) -cycloalkyl, (C 3 -C 6) -cycloalkyl-C 1 -C 2 cycloalkyl; C1-2 alkyl phenylalkyl optionally substituted by fluorine, chlorine, nitro, cyano, C1-C4alkyl, C1-C4alkoxy, or C1-C4-phenylalkyl; (C 1 -C 4) 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 alkylainocarbonylamino, C 1 -C 4 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 -CII = NR ⁹ , wherein the formula -CII = NR ⁹ , R &lt; ⁹ &gt; is optionally fluorine, chlorine, cyano, carboxy, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfonyl or C1-C4alkylsulfonyl; up to 6 carbon atoms; optionally a 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 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, (1-6C) alkylsulfonylamino phenylsulfonylamino or 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 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 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 1-4 alkyl optionally substituted by fluorine and / or chlorine; C 4 -C 4 alkyl, C 1 -C 4 alkylsulfinyl or C 1 -C 4 alkylsulfonyl optionally substituted by fluorine and / or chlorine, C 1 -C 4 dialkylaminosulfonyl or C 1 -C 4 alkoxycarbonyl the carbon atoms in the alkoxy moiety or the dimethylaminocarbonyl group; then R ³ represents a group of the formula wherein 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, further denotes an alkylthio group having 1 to 4 carbon atoms, SK 280209 Β6 C 1 -C 4 or C 1 -C 4 alkylsulfonyl optionally substituted by fluorine and / or chlorine or C 1 -C 4 dialkylaminosulfonyl; then R ³ represents a group of the general formula B ¹ '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 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, a (C 1 -C 4) alkoxycarbonyl group or a 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 formula wherein 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 ²⁵ R ²⁴ where 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 represents one of the following groups of formulas and their salts. A process for the preparation of a sulfonylaminocarbonyltriazolinone of formula (I) according to claim 1, characterized in that (a) reacting the triazolinones of general formula (Π) in which: R ¹ and R ² are as defined above with a sulfonyl isocyanates of the formula (ΠΙ) R ³ - SO ₂ - N = C = O (IH) in which R ³ is as defined above, optionally 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, C 1 -C 4 alkoxy, benzyloxy or phenoxy, 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) o in which R ¹ and R ² are as defined above, with the sulfonic acid amide derivatives of the general formula (VI) R ³ -SO ₂ -NH-CO-Z (VI) wherein R ³ has the abovementioned meaning and Z is as hereinbefore defined, 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) according to claim 1 as an active ingredient. Use of the sulfonylama-mercapto-triazolinones of 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 the sulfonylaminocarbonyltriazolinones of the formula (I) according to claim 1.