WO1999061429A1

WO1999061429A1 - Sulfonyl amino (thio)carbonyl triazoline (thi)ons having alkenyl substituents

Info

Publication number: WO1999061429A1
Application number: PCT/EP1999/003389
Authority: WO
Inventors: Klaus-Helmut Müller; Klaus König; Ernst Rudolf Gesing; Rolf Kirsten; Joachim Kluth; Markus Dollinger; Mark Wilhelm Drewes; Ingo Wetcholowsky; Gerd Hänssler; Klaus Stenzel; Randy Allen Myers
Original assignee: Bayer Aktiengesellschaft
Priority date: 1998-05-23
Filing date: 1999-05-17
Publication date: 1999-12-02
Also published as: EP1082312A1; AU4144499A; HK1039936A1; KR20010043551A; DE19823131A1; CN1311783A; CA2333068A1; JP2002516316A

Abstract

The invention relates to novel sulfonyl amino (thio)carbonyl triazoline (thi)ons having alkenyl substituents of formula (I) in which Q1 represents oxygen or sulfur; Q2 represents oxygen or sulfur; R1 represents hydrogen, amino, alkylidene amino or a respective optionally substituted radical from the series of alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkyl amino, dialkyl amino, alkanoyl amino, cycloalkyl, cycloalkyl alkyl, cycloalkyl amino, aryl and aryl alkyl; R2 optionally represents substituted alkenyl; R3 represents a respective optionally substituted radical from the series of alkyl, aryl alkyl, aryl and heteroaryl. The invention also relates to salts of the compounds of formula (I), to methods, to novel intermediate products for producing compounds of formula (I), and to the use thereof as herbicides and/or fungicides.

Description

Sulfonylamino (thio) carbonyltriazolin (thi) one with alkenyl substituents

The invention relates to new sulfonylamino (thio) carbonyltriazolin (thi) ones with alkenyl substituents, several processes and new intermediates for their preparation and their use as crop treatment agents, in particular as herbicides and as fungicides.

It is already known that certain sulfonylamino (thio) carbonyltriazolin (thi) one have herbicidal properties (cf. EP 341489, EP 422469, EP 425948, EP

431291. EP 507171, WO 96/22982). However, the action of these previously known compounds is not satisfactory in all respects.

The new sulfonylamino (thio) carbonyltriazolin (thi) ones with alkenyl substituents of the general formula (I)

in which

Ql represents oxygen or sulfur,

Q ^ represents oxygen or sulfur.

R.1 for hydrogen, amino, alkylidene amino or for an optionally substituted radical from the series alkyl, alkenyl. Alkynyl. Alkoxy.

Alkenyloxy, alkylamino, dialkylamino, alkanoylamino, cycloalkyl. Cycloalkylalkyl, cycloalkylamino, aryl and arylalkyl. R2 represents optionally substituted alkenyl and

R ^ represents an optionally substituted radical from the series alkyl, aralkyl, aryl and heteroaryl.

as well as salts of compounds of formula (I) found.

The new sulfonylamino (thio) carbonyltriazolin (thi) ones with alkenyl substituents of the general formula (I) are obtained if

(a) triazolin (thi) one of the general formula (II)

Q ¹

H - N, A N R '

(II)

R in which

Q, Rl and R ^ have the meaning given above.

with sulfonyl iso (thio) cyanates of the general formula (III)

R ³ -S0 ₂ -N = = Q ² (III)

in which

Q ² and R-> have the meaning given above.

if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, - _) -

or if you

(b) triazolin (thi) on derivatives of the general formula (IV)

in which

Q, Q-, Rl and R ^{2 have} the meaning given above and

Z represents halogen, alkoxy, aralkoxy or aryloxy,

with sulfonic acid amides of the general formula (V)

R -S0 ₂ -NH ₂ (V)

in which

R ^{3 has} the meaning given above,

optionally in the presence of an acid acceptor and optionally in

In the presence of a diluent,

or if you

(c) triazolin (thi) one of the general formula (II) Q ¹

H - N N A. R 'N

(II)

N

R 'in which

Q, R and R ^{2 have} the meaning given above,

with sulfonic acid amide derivatives of the general formula (VI)

R ³ -S0 ₂ -NH-CQ -Z (VI)

in which

Q ² and R ^{3 have} the meaning given above and

Z represents halogen, alkoxy, aralkoxy or aryloxy.

if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent.

or if you

(d) triazolin (thi) one of the general formula (II)

in which Q, R and R ^{2 have} the meaning given above,

with sulfonic acid halides of the general formula (VII)

R ³ -S0 ₂ -X (VII)

in which

R ^{J has} the meaning given above and

X represents halogen.

and metal (thio) cyanates of the general formula (VIII)

MQ ² CN (VIII)

in which

Q ^{2 has} the meaning entered above and

M represents an alkali metal or an alkaline earth metal equivalent.

if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,

and optionally converting the compounds of the formula (I) obtained by processes (a), (b), (c) or (d) into salts by customary methods.

The new sulfonylamino (thio) carbonyltriazolin (thi) ones with alkenyl substituents of the general formula (I) show interesting biological effects; they are particularly notable for their strong herbicidal and / or fungicidal activity. For the definitions in formula (I):

R preferably represents hydrogen, amino, C

for Cj-Cg-alkyl optionally substituted by fluorine, chlorine, bromine, cyano, C -C4-alkoxy, C [-C4-alkylcarbonyl or C \ -C4-alkoxycarbonyl, for each optionally by fluorine, chlorine and / or bromine-substituted C ₂ -Cg alkenyl or C -C -C alkynyl, for C 1 -Cg alkyloxy or C ₂ -Cg alkenyloxy, for C _j -Cg alkylamino optionally substituted by fluorine and / or chlorine, di- (-C-C4-alkyl) -amino or C-C4-alkyl-carbonylamino, for each optionally by fluorine, chlorine. Bromine and / or C 1 -C 4 -alkyl-substituted C -Cg-cycloalkyl or C3-C-cycloalkyl-Cι-C4-alkyl, or for each optionally by fluorine, chlorine, bromine, cyano, nitro, C1-C4-alkyl, trifluoromethyl , -C -C4 alkoxy and / or -C -C4 alkoxy carbonyl substituted phenyl or phenyl-Cj-C4-alkyl.

R ² preferably represents Co-Cg-alkenyl optionally substituted by cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, Cj-C4-A_koxy or C \ -C4-alkoxy-carbonyl.

R ³ preferably represents the grouping, where

R and R are the same or different and are hydrogen, fluorine, chlorine, bromine. Iodine. Nitro, C j-Cg-alkyl (which may be replaced by fluorine,

Chlorine. Bromine, cyano, carboxyl, Cj-C4-alkoxycarbonyl, _Cj-C4 alkyl amino-carbonyl, di- (C ι-C4-alkyl) -amino-carbonyl, C [-C 4 alkoxy,

C j -C4-alkyl-carbonyloxy, Cj-C4-alkoxy-carbonyloxy, CJ-C4- Alkylamino-carbonyloxy, C1 -C4 alkylthio, C1 -C4 alkylsulfonyl, C1 -C4 alkylsulfonyl, di (C1 -C4 alkyl) aminosulfonyl, C3-C6-CVCI0-alkyl or phenyl is substituted), for C2-C6-alkenyl (which may be replaced by fluorine, chlorine, bromine, cyano, C \ -C4-alkoxy-carbonyl

5 or phenyl is substituted) for C ₂ -C 6 alkynyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, C 1 -C 4 alkoxycarbonyl or phenyl), for C1 -C4 alkoxy (which is optionally substituted by fluorine , Chlorine, bromine, cyano, -C ₄ -C ₄ alkoxycarbonyl, C1 -C4 alkoxy, -C ₄ -C ₄ alkylthio, -C ₄ -C ₄ alkylsulfonyl, -C ₄ -C ₄ alkylsu_fonyl

10 or C3-C6-cycloalkyl is substituted) for C j -C ^ alkylthio (which is optionally by fluorine, chlorine, bromine, cyano, -C -C4-alkoxycarbonyl, -C-C4-alkylthio, C \ -C4-alkylsulfionyl or C 1 -C 4 alkyl sulfonyl is substituted), for C -Cg alkenyloxy (which 'ses- if by fluorine, chlorine, bromine, cyano or C -C 4 alkox carbonyl

15 is substituted), for C ₂ -C6 alkenylthio (which may be replaced by

Fluorine, chlorine, bromine, cyano, nitro, C] -C3-alkylthio or C1-C4-alkoxy-carbonyl is substituted), C3-Cg-alkynyloxy, C3-Cg-alkynyl-

thio or stand for the rest -S (O) -R, where

20 p stands for the numbers 1 or 2 and

R for C1-C4-alkyl (which may be replaced by fluorine, chlorine.

Bromine, cyano or C _} -C4 alkoxy-carbonyl is substituted), C3-C <5-alkenyl, C ₃ -C ₆ alkynyl, C ι -C ₄ alkoxy. C1 -C4-

25 alkoxy-C | -C4-alkylamino, C [-C4-alkylamino, di- (C ι -C4-

7 alkyl) amino, phenyl or the radical -NHOR, where 7 R for C] -Ci 2-alkyl (which may be replaced by fluorine, chlorine.

Cyano. C1-C4 alkoxy, -C-C4-alkylthio, Cι. -C4-alkyl-sulfinyl, C | -C4-alkylsulfonyl, C \ -C4-alkyl-carbonyl, C1-C4-

Alkoxy-carbonyl, -C-C4-alkylamino-carbonyl or di- (C - C4-alkyl) -amino-carbonyl is substituted), for C3-C6-alkenyl

(which is optionally substituted by fluorine, chlorine or bromine), C3-Cö-alkali yl, Cß-Cg-cycloalkyl, C3-Cö-cyclo-a_kyl-C} -C ₂ alkyl, phenyl-Cι-C ₂ alkyl (which is optionally substituted by fluorine, chlorine, nitro, cyano, C1-C4-alkyl, C1-C4-alkoxy or C] -C4-alkoxy-carbonyl), for

Diphenylmethyl or for phenyl (which is optionally substituted by fluorine, chlorine, nitro, cyano, C 1 -C 4 alkyl, trifluoromethyl, C 1 -C 4 alkoxy, C 1 -C 4 fluoroalkoxy, C 1 -C 4 alkylthio,

Trifluoromethylthio or C 1 -C 4 alkoxycarbonyl is substituted),

5 d / or R further for phenyl or phenoxy, for -C-C4-alkylcarbonylamino, C1-C4-alkoxy-carbonylam.no, Cι-C4-alkylamino-carbonylamino, di- (Cι -C4-alkyl) -amino-carbonylamino, or for g the radical -CO-R, where

R ^ö for hydrogen, C ^ Cg-alkyl, C3-C ₆ -cycloalkyl, C ^ Cg-

Alkoxy, C3-C6-cycloalkoxy, C3-Cg-alkenyloxy, C1-C4-

Alkylthio, -C-C4-alkylamino. C1 -C4- alkoxy amino, C 1 -C4- alkoxy -CC-C4-alkylamino or di- (C 1-C4-alkyD-am.no (which are optionally substituted by fluorine and / or chlorine), R and / or R furthermore for trimethylsilyl, thiazolinyl, l, 2,4-oxadiazol-5-yl, 3-methyl-l, 2,4-oxadiazol-5-yl, l, 3-dioxolan-2-yl, C. _j -C4-alkyl-sulfonyloxy, di- (-C-C4-alkyl) -aminosulfonylamino or for the rest g -CH = NR, where

R for optionally by fluorine, chlorine. Cyano, carboxy, Ci -

C4-Alkoxy, -CC alkylthio, C ₁ -C alkylsulfonyl or C \ - C4-alkylsulfonyl substituted Cj-Cg-alkyl. for benzyl optionally substituted by fluorine or chlorine. for C3-C which may be substituted by fluorine or chlorine -

Alkenyl or C3-Cg-alkynyl, for optionally by fluorine, chlorine, bromine, Cj-C4-alkyl, C] -C4-alkoxy, trifluoromethyl,

Trifluoromethoxy or trifluoromethylthio substituted phenyl, for optionally substituted by fluorine and / or chlorine Cj-Cg-alkoxy, C3-Cg-alkenyloxy, C3-C-alkynyloxy or

Benzyloxy, for amino, C1-C4- alkylam.no, di- (-C-C4-alkyl) - amino. Phenylamino, -C-C4-alkyl-carbonylamino. C1-C4 alkoxy carbonylamino. C 4 -C 4 alkylsulfonylamino or phenylsulfonylamino which is optionally substituted by fluorine, chlorine, bromine or methyl.

R ^{J is also} preferred

wherein R 10 represents hydrogen or C - C ^ - alkyl,

R 11 and R 12 are the same or different and are hydrogen,

Fluorine, chlorine, bromine, nitro, cyano. C1-C4- alkyl (which is optionally substituted by fluorine and / or chlorine), C1 - C4-alkoxy (which is optionally substituted by fluorine and / or chlorine), carboxy, C 1 -C4-alkoxycarbonyl, dimethylaminocarbonyl, Cι -C4-alkylsulfonyl or di- (C - C4-alkyl) -aminosulfonyl.

R ^{J is also} preferred

wherein

R and R are the same or different and represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, C 1 -C 4 -alkyl (which is optionally substituted by fluorine and / or chlorine) or C1-C4-alkoxy (which is optionally substituted by fluorine and /or

Chlorine is substituted).

R ^{J is also} preferred

wherein

R and R are the same or different and are hydrogen, fluorine, chlorine, bromine, nitro, cyano, C1-C4-alkyl (which is optionally substituted by fluorine and / or chlorine), C \ - C4-alkoxy (which is optionally substituted by fluorine and / or chlorine is substituted), for C -C4 alkylthio. C _] -C4-alkyl-sulfinyl or -C-C4-alkylsulfonyl (which are optionally substituted by fluorine and / or chlorine), for amino-sulfonyl, mono- (-C-C4-alkyl) -aminosulfonyl, for di- (Cι- C4-alkyl) -aminosulfonyl or -C-C4-alkoxy-carbonyl or

Dimethylaminocarbonyl stand.

R ^{3 is also} preferred

wherein

R 17 and R 18 are the same or different and are hydrogen,

Fluorine, chlorine, bromine, C1-C4-alkyl (which is optionally substituted by fluorine and / or bromine), C1-C4-alkoxy

(which is optionally substituted by fluorine and / or chlorine) for C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfinyl or C 1 -C 4 alkylsulfonyl (which are optionally substituted by fluorine and / or chlorine), or are di- (C 1 -C 4 alkyl) - aminosulfonyl.

R ^{3 is also} preferred

wherein

19 20

R and R are the same or different and represent hydrogen,

Fluorine, chlorine, bromine, cyano, nitro, C1-C4- alkyl (which is optionally substituted by fluorine and or chlorine), C i- C4-alkoxy (which is optionally substituted by fluorine and / or chlorine), -C-C4- Alkylthio, C _j ^ alkylsulfinyl or -C-C4-alkylsulfonyl (which are optionally substituted by fluorine and / or chlorine), di- (C ι-C4-alkyl) -aminosulfonyl, Cι-C4-alkoxy-carbonyl or dimethylamino - carbonyl stand, and

A stands for oxygen, sulfur or the grouping N-T, where

T for hydrogen. C 1 -C 4 -alkyl (which is optionally substituted by fluorine, chlorine, bromine or cyano),

C3-C-cycloalkyl, benzyl, phenyl (which may be replaced by fluorine, chlorine, bromine or nitro is substituted), C -C4-alkylcarbonyl, -C-C4-alkoxycarbonyl or di- (C -C4-alkyl) -aminocarbonyl.

R ^{3 is also} preferred

, 21

N for the rest ₂

R

wherein

R 21 and R 22 are the same or different and represent hydrogen, C

C4- alkyl, halogen, C -C4-alkoxy-carbonyl, -C-C4-alkoxy or Cι-C4-haloalkoxy,

Y ür Sc wee o er e rupperung - stands, where

93 R represents hydrogen or C 1 -C 4 alkyl.

R ^{3 is also} preferred

wherein R ^{24 is} hydrogen, C -C ₄ alkyl. Benzyl. Pyridyl, quinolinyl or phenyl,

25 R for hydrogen, halogen, cyano, nitro, C i -C4 alkyl (which is optionally substituted by fluorine and or chlorine), C -C4 alkoxy (which is optionally substituted by fluorine and / or

Chlorine is substituted), dioxolanyl or -CC-C4-alkoxycarbonyl, and

f R represents hydrogen, halogen or C 1 -C 4 alkyl.

The invention further preferably sodium, potassium, magnesium, calcium, ammonium, -C-C4 ~ alkyl ammonium. Di- (C -C4-alkyl) - ammonium-, tri- (Cι-C4-alkyl) -ammonium-, tetra- (C-C4-alkyl) -ammonium, tri- (Cι-C4-alkyl) -sulfonium- , C5- or Cg-cycloalkyl-ammonium and di- (C -C ₂ -alkyl) -benzyl-ammonium salts of compounds of the formula (I) in which Q,

Q ² . R, R ² and R ^{3 have} the meanings preferably given above.

R stands in particular for fluorine, if appropriate. Chlorine, cyano, methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl, for propenyl, butenyl, propynyl or butynyl optionally substituted by fluorine, chlorine or bromine, for methoxy, ethoxy, n- or i-propoxy or for Allyloxy. for methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino, or for optionally by fluorine, chlorine. Bromine. Methyl or ethyl substituted cyclopropyl, R ² stands in particular for ethenyl, propenyl or butenyl optionally substituted by cyano, fluorine, chlorine and / or bromine.

R ³ stands in particular for the rest

wherein

4 R for fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy. n- or i-propoxy, difluoromethoxy, trifluoromethoxy, 2-chloro-ethoxy, 2-fluoro-ethoxy, 2,2-difluoro-ethoxy,

2,2,2-trifluoro-ethoxy, 1, 1, 2,2-tetrafluoro-ethoxy, 1, 1, 2,2,2-pentafluoro-ethoxy, 2-methoxy-ethoxy, cyclopropylmethoxy, methylthio, ethylthio, n- or i-propylthio, 2-fluoro-ethylthio, allyloxy, propargyloxy,

Methylsulfinyl, ethylsulfmyl, methylsulfonyl, ethylsulfonyl, dimethylaminosulfonyl, diethylaminosulfonyl, N-methoxy-N-methylaminosulfonyl, phenyl, phenoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl and

R represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy,

Trifluoromethoxy, methylthio or ethylthio.

Furthermore R ³ stands in particular for

woπn

R ^{10 represents} hydrogen,

R represents fluorine, chlorine, bromine, methyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, methoxycarbonyl, ethoxycarbonvl, methvlsulfonvl or dimethylaminosulfonyl

1

R stands for hydrogen.

Furthermore, R ^J stands in particular for the rest

O in what

R for methyl, ethyl. is n- or i-propyl.

Furthermore, R ³ stands in particular for the rest

wherein

R 4 represents methyl, ethyl, n- or i-propyl, phenyl or pvridyl. R ^ represents hydrogen, fluorine, chlorine or bromine, and

R ² ^ represents fluorine, chlorine, bromine, methoxycarbonyl or ethoxycarbonyl.

The general or preferred radical definitions given above apply both to the end products of the formula (I) and correspondingly to the starting materials or intermediates required in each case for the preparation. These radical definitions can be combined with one another as desired, that is to say also between the specified ranges of preferred compounds.

Preferred compounds according to the invention are those of the formula (I) in which there is a combination of the meanings listed above as preferred.

According to the invention, those compounds of the formula ^r \) are particularly preferred in which there is a combination of the meanings listed above as being particularly preferred.

The hydrocarbon radicals mentioned in the radical definitions, such as alkyl, alkenyl or alkynyl, also in combinations with heteroatoms. as in alkoxy. Alkylthio or alkylamino, even if this is not expressly stated, can be straight-chain or branched.

Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine. Chlorine or bromine, especially for fluorine or chlorine.

With certain compounds of the formula (I) according to the invention, cis / trans isomerism can occur. In these cases, the invention encompasses both geometric isomers and their mixtures (in any proportions). For example, if 2-trifluoromethoxy-phenylsulfonyl isocyanate and 4-ethyl-5- (2-fluoropropen-l-yl) -2,4-dihydro-3H-l, 2,4-triazol-3-one (trans -Isomer) as starting materials, the course of the reaction in process (a) according to the invention can be outlined using the following formula:

O

If, for example, 2-ethylthio-benzenesulfonamide and 2-chlorocarbonyl-4-cyclopropyl-5- (1,2-dichloropropen-l-yl) -2,4-dihydro-3H-1,2,4-triazol-3-one are used (trans-isomer) as starting materials, the course of the reaction in process (b) according to the invention can be outlined using the following formula:

If, for example, N-methoxycarbonyl-2-methoxy-benzenesulfonamide and 5- (l-bromopropen-2-yl) -4-methyl-2,4-dihydro-3H-l, 2,4-triazol-3-one are used rtrans isomer) as starting materials, the course of the reaction in process (c) according to the invention can be outlined using the following formula:

O

If, for example, 2-chloro-6-methyl-benzenesulfonic acid chloride, 4-allyl-

5- (propen-l-yl) -2,4-dihydro-3H-l, 2,4-triazol-3-one (trans isomer) and sodium cyanate as starting materials, the course of the reaction in process (d) according to the invention can be outlined using the following formula:

Formula (II) provides a general definition of the triazolin (thi) ones to be used as starting materials in processes (a), (c) and (d) for the preparation of compounds of the formula (I).

In formula (II), Q. R and R ² preferably or in particular those

Meanings which have already been given above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for Q, R and R ² .

The triazolin (thi) one of the general formula (II) are not yet known from the literature: as new substances, they are also the subject of the present application.

The new triazolin (thi) one of the general formula (II) is obtained if one

(α) Iso. thio) cyanates of the general formula (IX) Q1 = _C = NR ¹ (IX) in which

Ql and R have the meaning given above,

with hydrazides of the general formula (X)

H ₂ N-NH-CO-R ² (X)

in which

R ^{2 has} the meaning given above,

optionally in the presence of diluents, e.g. Isopropanol or water, optionally in the presence of a reaction auxiliary, e.g. Sodium hydroxide, reacted at temperatures between 0 ° C and 100 ° C [whereby isomerization can occur as a result of a double bond shift] and worked up in the usual way (see the preparation examples),

or if you

(β) (thio) semicarbazides of the general formula (XI)

in which

R and Ql have the meaning given above.

with carboxylic acids or their derivatives of the general formula (XII) R ² -CO-Y (XII)

in which

R ^{2 has} the meaning given above and

Y stands for hydroxy, halogen or the grouping -O-CO-R-.

optionally in the presence of a diluent, e.g. Sulfolane, optionally in the presence of a reaction auxiliary, e.g. Sodium hydroxide, and optionally in the presence of a stabilizer such as e.g. Hydroquinone. reacted at temperatures between 0 ° C and 100 ° C and worked up in the usual way (cf. the manufacturing examples).

The process (a) according to the invention for the preparation of compounds of

Formula (I) sulfonyliso (thio) cyanates to be used as starting materials are generally defined by the formula (III).

In formula (III), Q ² and R ³ preferably or in particular have those meanings. which have already been given above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for Q ² and R ³ .

The starting materials of the formula (III) are known and / or can be prepared by processes known per se (cf. US Pat. No. 4,127,405. US Pat. No. 4,169,719. US Pat

4371391, EP-A 7687, EP-A 13480. EP-A 21641, EP-A 23141. EP-A 23422. EP-A 30139, EP-A 35893, EP-A 44808, EP-A 44809, EP-A 48143. EP-A 51466. EP-A 64322, EP-A 70041. EP-A 173312).

The triazolin (thi) on- to be used as starting materials in process (b) according to the invention for the preparation of the compounds of the general formula (I) Derivatives are generally defined by the formula (IV). Have in formula (IV)

Q, Q ² , R and R ² preferably or in particular those meanings which have already been mentioned above in connection with the description of the compounds of the formula

(I) were indicated as preferred or as particularly preferred for Q, Q ² , R and R ² ; Z preferably represents fluorine, chlorine, bromine, methoxy, ethoxy, benzyloxy or phenoxy, in particular methoxy or phenoxy.

The starting materials of the formula (IV) are not yet known from the literature; as new substances, they are also the subject of the present application.

The new compounds of the formula (IV) are obtained if triazolin (thi) one of the general formula (II)

Q '

(II)

N = (

FT in which

Q. R and R ^{2 have} the meaning given above,

with carbonic acid derivatives of the general formula (XIII)

in which

Q ² and Z have the meaning given above and

Z represents halogen (especially chlorine), alkoxy (especially methoxy), aralkoxy (especially benzyloxy) or aryloxy (especially phenoxy). optionally in the presence of an acid acceptor, such as sodium or potassium hydride, sodium or potassium hydroxide, sodium or potassium t-butoxide, and optionally in the presence of a diluent, such as tetrahydrofuran or dimethoxvethane, or in a two-phase system of water and an organic solvent , such as methylene chloride or chloroform, at

Temperatures between 0 ° C and 100 ° C implemented.

Formula (V) provides a general definition of the sulfonic acid amides to be used as starting materials in process (b) according to the invention for the preparation of the compounds of the general formula (I). In formula (V), R ³ preferably or in particular has the meaning which has already been given above in connection with the description of the compounds of the formula (I) as preferred or as particularly preferred for R ³ .

The starting materials of the formula (V) are known and or can be prepared by processes known per se (cf. US Pat. No. 4,127,405, US Pat. No. 4,169,719, US Pat. No. 4,37,1391, EP-A 7687, EP-A 13480, EP-A 21641, EP-A 23141, EP-A 23422, EP-A 30139, EP-A 35893, EP-A 44808, EP-A 44809, EP-A 48143, EP-A 51466, EP-A 64322, EP-A 70041, EP-A 173312).

Formula (VI) provides a general definition of the sulfonamide derivatives to be used as starting materials in process (c) according to the invention for the preparation of the compounds of the formula (I). In formula (VI), Q ² and R ³ preferably or in particular have those meanings which have already been given above in connection with the description of the compounds of the formula (I) as preferred or as particularly preferred for Q ² and R ³ were; Z preferably represents fluorine, chlorine, bromine, methoxy, ethoxy, benzyloxy or phenoxy, in particular methoxy or phenoxy. - 25 -

The starting materials of the formula (VI) are known and or can be prepared by processes known per se.

Formula (VII) provides a general definition of the sulfonic acid halides to be used as starting materials in process (d) according to the invention for the preparation of the compounds of the formula (I). In formula (VII), R ³ preferably or in particular has the meaning which has already been given above in connection with the description of the compounds of the formula (I) as preferred or as particularly preferred for R ³ ; X preferably represents fluorine. Chlorine or bromine, especially for chlorine.

The starting materials of the formula (VII) are known and / or can be prepared by processes known per se.

The new intermediates of formulas (II) and (IV) above. which differ only in that the 2-position is unsubstituted or substituted by an acyl radical -CQ ² -Z can be summarized by the following formula (XIV):

in which

R. R ² and Q have the meanings given above for formula (I) and A represents hydrogen or the group -CQ ² -Z, wherein

Q ^{2 has} the meaning given above for formula (I) and

Z for halogen, alkoxy. Aralkoxy or aryloxy.

With regard to the preferred and particularly preferred meanings of all variable radicals of the formula (XIV), the information given above for the compounds of the formulas (II) and (IV) applies.

Processes (a), (b), (c) and (d) according to the invention for the preparation of the new compounds of the formula (I) are preferably carried out using diluents. Practically all inert organic solvents can be used as diluents. 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 and dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxane; Ketones such as acetone, methyl ethyl, methyl isopropyl and methyl isobutyl ketone: esters such as methyl acetate and ethyl acetate; Nitriles such as Acetonitrile and propionitrile; Amides such as Dimethylformamide, dimethylacetamide and N-methylpyrrolidone, as well as dimethyl sulfoxide, tetramethylene sulfone and hexamethyl phosphoric acid triamide.

As reaction auxiliaries or as acid acceptors in the processes (a), (b), (c) and (d) according to the invention, it is possible to use all acid binders which can customarily be used for such reactions. Alkali metal hydroxides such as sodium and potassium hydroxide are preferred. Alkaline earth metal hydroxides such as calcium hydroxide. Alkali carbonates and alko-olates such as sodium and potassium carbonate, sodium and potassium tert-butoxide, and also basic nitrogen compounds such as trimethylamine, triethylamine. Tripropylamine, tributylamine, Diisobutylamine, dicyclohexylamine, ethyldiisopropylamine, ethyldicyclohexylamine, N, N-dimethylbenzylamine, N, N-dimethyl-aniline, pyridine, 2-methyl, 3-methyl, 4-methyl, 2,4-dimethyl, 2,6- Dimethyl, 2-ethyl, 4-ethyl and 5-ethyl-2-methyl-pyridine, 1,5-diazabicyclo [4,3,0] non-5-ene (DBN), 1,8-diazabicyclo - [5.4.0] -undec-7-ene (DBU) and 1,4-diazabicyclo- [2,2,2] -octane (DABCO).

The reaction temperatures can be varied within a wide range in processes (a), (b), (c) and (d). In general, temperatures between -20-C and + 100 ° C, preferably at temperatures between 0 ° C and + 80 ° C.

Processes (a), (b), (c) and (d) according to the invention are generally carried out under atmospheric pressure. However, it is also possible to work under increased or reduced pressure.

To carry out processes (a), (b), (c) and (d) according to the invention, the starting materials required in each case are generally used in approximately equimolar amounts. However, it is also possible to use a larger excess of one of the components used in each case. The reactions are generally carried out in a suitable diluent in the presence of an acid acceptor, and the reaction mixture is stirred for several hours at the temperature required in each case. Working up in the processes (a), (b), (c) and (d) according to the invention is in each case carried out by customary methods (cf. the preparation examples).

If appropriate, salts can be prepared from the compounds of the general formula (I) according to the invention. Such salts are obtained in a simple manner by customary salt formation methods, for example by dissolving or dispersing a compound of the formula (I) in a suitable solvent, such as, for example, methylene chloride, acetone, tert-butyl methyl ether or toluene, and adding a suitable base. The salts can then be isolated - if appropriate after prolonged stirring - by concentration or suction. - 78 -

The active compounds according to the invention can be used as defoliants. Desiccants, herbicides and especially as weed killers. Weeds in the broadest sense are understood to mean all plants that grow up in places where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.

The active compounds according to the invention can e.g. can be used in the following plants:

Dicot weeds of the genus: Sinapis. Lepidium. Galium. Stellaria. Matricaria.

Anthemis. Galinsoga, Chenopodium. Urtica. Senecio, Amaranthus. Portulaca.

Xanthium. Convolvulus, Ipomoea. Polygonum, Sesbania. Ambrosia. Cirsium.

Carduus. Sonchus, Solanum, Rorippa. Rotala. Lindernia. Lamium. Veronica. Abutilon. Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium.

Ranunculus, Taraxacum.

Dicotyledon cultures of the genera: Gossypium. Glycine, Beta. Daucus. Phaseolus, Pisum. Solanum, Linum. Ipomoea. Vicia. Nicotiana. Lycopersicon. Arachis. Brassica. Lactuca. Cucumis, cucurbita.

Monocotyledonous weeds of the genera: Echinochloa, Setaria. Panicum, Digitaria. Phleum. Poa, Festuca, Eleusine, Brachiaria. Lolium, Bromus, Avena, Cyperus, Sorghum. Agropyron. Cynodon. Monochoria. Fimbristylis, Sagittaria. Eleocharis. Scirpus. Paspalum, Ischaemum, Sphenoclea. Dactyloctenium. Agrostis, Alopecurus.

Apera.

Monocot cultures of the genera: Oryza. Zea. Triticum. Hordeum. Avena. Seeale. Sorghum, Panicum, Saccharum. Pineapple, asparagus. Allium. However, the use of the active compounds according to the invention is by no means restricted to these genera, but extends in the same way to other plants.

Depending on the concentration, the compounds are suitable for total weed control, e.g. on industrial and track systems and on paths and squares with and without tree cover. Likewise, the compounds for weed control in permanent crops, e.g. Forest, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports turf and pastures and for selective weed control in annual crops.

The compounds of formula (I) according to the invention are particularly suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops both in the pre-emergence and in the post-emergence process.

In addition, the active compounds according to the invention also have a strong microbicidal action and can be used practically to combat unwanted microorganisms. The active ingredients are suitable in suitable concentrations for use as fungicides and / or bactericides.

Fungicidal agents in crop protection are used to control plasmidiophoromycetes, oomycetes and chytridiomycetes. Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes.

Bactericidal agents are used in plant protection to combat Pseudomonadaeae, Rhizobiaceae. Enterobacteriaceae. Corynebacteriaceae and Streptomycetaceae used.

Some pathogens of fungal and bacterial diseases that fall under the generic names listed above may be mentioned as examples, but not by way of limitation: Xanthomonas species, such as, for example, Xanthomonas campestris pv. Oryzae;

Pseudomonas species. such as Pseudomonas syringae pv. Lachrymans;

Erwinia species, such as, for example, Erwinia amylovora;

Pyfhium species, such as, for example, Pythium ultimum;

Phytophthora species. such as Phytophthora infestans;

Pseudoperonospora species. such as Pseudoperonospora humuli or

Pseudoperonospora cubensis;

Plasmopara species, such as, for example, Plasmopara viticola;

Bremia species, such as, for example, Bremia lactucae;

Peronospora species, such as, for example, Peronospora pisi or P. brassicae:

Erysiphe species, such as, for example, Erysiphe graminis;

Sphaerotheca species. such as Sphaerotheca fuliginea:

Podosphaera species. such as Podosphaera leucotricha:

Venturia species. such as Venturia inaequalis;

Pyrenophora species. such as Pyrenophora teres or P. graminea

(Conidial form: Drechslera. Syn: Helminthosporium); Cochliobolus species, such as, for example, Cochliobolus sativus

(Conidial form: Drechslera, Syn: Helminthosporium);

Uromyces species, such as, for example, Uromyces appendiculatus;

Puccinia species, such as, for example, Puccinia recondita;

Sclerotinia species, such as, for example, Sclerotinia sclerotiorum;

Tilletia species, such as, for example, Tilletia caries;

Ustilago species, such as, for example, Ustilago nuda or Ustilago avenae;

Pellicularia species, such as, for example, Pellicularia sasakii;

Pyricularia species, such as, for example, Pyricularia oryzae;

Fusarium species, such as, for example, Fusarium culmorum;

Botrytis species, such as, for example, Botrytis cinerea;

Septoria species, such as, for example, Septoria nodorum;

Leptosphaeria species, such as, for example, Leptosphaeria nodorum;

Cercospora species, such as, for example, Cercospora canescens;

Alternaria species, such as, for example, Alternaria brassicae;

Pseudocercosporella species, such as, for example, Pseudocercosporella heφotrichoides. The fact that the active compounds are well tolerated by plants in the concentrations required to combat plant diseases permits treatment of above-ground parts of plants, of propagation stock and seeds, and of the soil.

The active compounds according to the invention can be used with good success to combat diseases in fruit and vegetable production, for example against Podosphaera species, and to combat rice diseases, for example Pyricularia oryzae (protective and systemic).

The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions. Powder. Dusts, pastes, soluble powders, granules, suspension emulsion concentrates. Active ingredient-impregnated natural and synthetic substances as well as very fine encapsulation in polymeric substances.

These formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, ie liquid solvents and / or solid carriers, optionally using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents.

If water is used as an extender, e.g. organic solvents can also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene. or alkyl naphthalenes. chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes. Chloroethylene or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and 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, and water. Possible solid carriers are: for example ammonium salts and natural rock powders such as kaolins, clays, talc. Chalk, quartz. Attapulgite, montmorillonite or diatomaceous earth and synthetic rock flour, such as highly disperse silica, aluminum oxide and silicates, are suitable as solid carriers for granules: eg broken and fractionated natural rocks such as calcite,

Marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks: emulsifying and / or foaming agents are possible: e.g. nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters. Polyoxyethylene fatty alcohol

Ether. e.g. Alkylaryl polyglycol ether. Alkyl sulfonates. Alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: e.g. Lignin sulfite leaching and methyl cellulose.

Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate and natural phospholipids, can be used in the formulations. such as cephalins and lecithins and synthetic phospholipids. Other additives can be mineral and vegetable oils.

Dyes such as inorganic pigments can be used. e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin. Azo and metal phthalocyanine dyes and trace nutrients such as salts of iron. Manganese. Boron, copper. Cobalt, molybdenum and zinc can be used.

The formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.

The active compounds according to the invention, as such or in their formulations, can also be used for combating weeds, in a mixture with known herbicides, finished formulations or tank mixes being possible. Known herbicides are suitable for the mixtures, for example

Acetochlor, Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne. Amidochlor, amidosulfuron, anilofos, asulam, atrazine, azafenidin, azimsulfuron, benazolin (-ethyl), benfuresate, bensulfuron (-methyl), bentazone,

Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bispyribac (-sodium), Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butroxydim. Butylates. Cafenstrole, caloxydim, carbetamide. Carfentrazone (-ethyl), Chlomethoxvfen, Chloramben, Chloridazon, Chlorimuron (-ethyl). Chloronitrofen, chlorosulfuron. Chlortoluron, Cin- methylin, Cinosulfuron, Clethodim, Clodinafop (-propargyl), Clomazone, Clomeprop,

Clopyralid. Clopyrasulfuron (-methyl), Cloransulam (-methyl), Cumyluron, Cyanazine, Cycloate, Cyclosulfamuron. Cycloxydim, cyhalofop (-butyl), 2.4-D. 2.4-DB, 2,4-DP, desmedipham, dialates, dicamba, diclofop (-methyl), diclosulam, diethyl (-ethyl), difenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate. Dimethachlor, Dimethametryn, Dimethenamid, Dimexyflam, Dinitramine. ^; ) iphenamide, Diquat, Dithiopyr, Diuron, Dymron, Epoprodan, EPTC, Esprocarb, Lthalfluralin, Ethametsulfuron (-methyl), Ethofumesate, Ethoxyfen, Ethoxysulfuron, Eto- benzanid. Fenoxaprop (-P-ethyl), Flamprop (-isopropyl), Flamprop (-isopropyl-L), Flamprop (-methyl), Flazasulfuron. Fluazifop (-P-butyl), flumetsulam, flumiclorac (- pentyl), flumioxazin, flumipropyn, flumetsulam. Fluometuron, fluorochloridones,

Fluoroglycofen (ethyl), flupoxam. Flupropacil. Fluφyrsulfuron (-methyl, -sodium), Flurenol (-butyl), Fluridone, Fluroxypyr (-meptyl), Fluφrimidol, Flurtamone, Fluothiacet (-methyl), Fluthiamide, Fomesafen, Glufosinate (-ammonium), Glyphosate (- isopropyl , Halosafen. Haloxyfop (-ethoxyethyl), Haloxyfop (-P-methyl), Hexazinone, Imazamethabenz (-methyl), Imazamethapyr, Imazamox, Imazapyr,

Imazaquin. Imazethapyr. Imazosulfuron, iodosulfuron, ioxynil. isopropaline. Isoproturon, Isouron, Isoxaben. Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil, Linuron. MCPA. MCPP, Mefenacet, Metamitron, Metazachlor, Methabenzthiazuron. Metobenzuron. Metobromuron. (alpha-) metolachlor, metosulam. Metoxuron, Metribuzin, Metsulfuron (-methyl), Molinate. Monolinuron, naproanilide. Napropamide. Neburon. Nicosulfuron. Norflurazon. Orbencarb. Oryzalin, oxadiargyl, oxadiazon. Oxa- sulfuron. Oxaziclomefone. Oxyfluorfen, paraquat. Pelargonic acid. Pendimethalin. Pentoxazone, Phenmedipham, Piperophos, Pretilachlor, Primisulfuron (-methyl), Prometryn, Propachlor, Propanil, Propaquizafop, Propisochlor, Propyzamide, Prosulfocarb, Prosulftiron, Pyraflufen (-ethyl), Pyrazolate, Pyrazosulfuron- (ethyl), Pyribenzoxim, Pyributicarb, Pyridate, Pyriminobac (-methyl), Pyrithiobac (- sodium), Quinchlorac. Quinmerac. Quinoclamine, Quizalofop (-P-ethyl), Quizalofop (-P-tefuryl), Rimsulfuron. Sethoxydim. Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Sulfosulfuron, Tebutam, Tebuthiuron, Terbuthylazine, Terbutryn, Thenylchlor, Thiafluamide, Thiazopyr, Thidiazimin, Thifensulfuron (-methyl), Tiocarbazil, Tralkoxydim, Triallate. Triasulfuron. Tribenuron (-methyl), triclopyr, tridiphane, trifluralin and triflusulfuron.

Also a mixture with other known active ingredients, such as fungicides, insecticides. Acaricides, nematicides. Protective substances against bird feed, plant nutrients and agents that improve soil structure are possible.

The active compounds as such, in the form of their formulations or the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions. Powders, pastes and granules can be used. They are used in the usual way, e.g. by pouring. Splash, spray. Scatter.

The active compounds according to the invention can be applied both before and after emergence of the plants. They can also be worked into the soil before sowing.

The amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. In general, the application rates are between 1 g and 10 kg of active ingredient per hectare of soil, preferably between 5 g and 5 kg per ha.

The preparation and use of the active compounds according to the invention can be seen from the examples below. Manufacturing examples:

example 1

(Method (a))

A mixture of 1.4 g (10 mmol) of 4-methyl-5- (propen-l-yl) -2,4-dihydro-3H-l, 2,4-triazol-3-one [trans isomer (II-l )], 3.0 g (12 mmol) of 2-difluoromethoxy-phenylsulfonyl isocyanate and 40 ml of acetonitrile is stirred for 15 hours at room temperature (approx. 20 ° C.) and then concentrated in a water jet vacuum. The residue is stirred with isopropanol / petroleum ether and the crystalline product is isolated by suction.

3.7 g (95% of theory) of 2- (2-difluoromethoxyphenylsulfonylaminocarbonyl) -4-methyl-5- (propen-l -yl) -2,4-dihydro-3H-1,2 are obtained. 4-triazol-3-one [trans form] with a melting point of 173 ° C.

Example 2

(Method (b))

2.64 g (10 mmol) of N, N-dimethyl-benzene-1,2-disulfonamide are taken up in 30 ml of toluene and at room temperature (approx. 20 ° C) with 1.52 g (10 mmol) of 1,8-diaza- bicyclo- [5,4,0] -undec-7-ene (DBU) added. The mixture is stirred at room temperature for 30 minutes and then with a solution of 2.6 g (10 mmol) of 4-methyl-2-phenoxycarbonyl-5- (propen-l-yl) -2,4-dihydro-3H-1, 2,4-triazol-3-one [mixture of isomers: 70% trans / 30% ice] in 25 ml of acetonitrile was added dropwise. The reaction mixture is stirred for four hours at room temperature and then concentrated in a water jet vacuum. The residue is shaken with methylene chloride and 2N hydrochloric acid, the organic phase is separated off, dried with sodium sulfate and filtered. The filtrate is concentrated in a water jet vacuum, the residue is stirred with ethyl acetate / petroleum ether and the crystalline product is isolated by suction.

2.5 g (58% of theory) of 2- (2-dimethylaminosulfonylphenylsulfonylaminocarbonyl) -4-methyl-5- (propen-l-yl) -2,4-dihydro-3H-l, 2.4- triazol-3-one with a melting point of 163 ° C [as a mixture of isomers: 72% trans / 28% ice].

Analogously to Preparation Examples 1 and 2 and in accordance with the general description of the preparation processes according to the invention, the compounds of the formula (I) listed in Table 1 below can also be prepared, for example.

Table 1: Examples of the compounds of the formula (I)

Table 1: (continued)

Table 1: (continued)

Table 1: (continued)

Table 1: (continued)

Table 1: (continued)

Table 1: (continued)

*) Comments on the stereochemical information for R ²

1) The active compounds of the formula (I) prepared from the trans isomer (II-1) described below also all have the trans configuration (denoted by “trans”).

2) The same applies to all active ingredients (I) produced from the trans isomer (II-4). The trans isomer (II-4) is already in its synthesis in a purity of> 95%; the cis isomer has not been isolated so far.

3) In some cases, however, (II) -cis / trans mixtures obtained from triazolinone (II) mother liquors were also converted into the corresponding phenylurethanes (IV) (likewise cis / trans isomer mixtures) and then with sulfonamides (V) converted to active ingredients (I) according to production process (b), which were then also cis / trans isomer mixtures of changing compositions, depending on the solubility of the isomers.

In these cases, the isomer composition of the end product (I) obtained is given in percent (%) (determined from the respective iH-NMR spectrum). For example, the indication means

trans / cis 72:28 for the active substance concerned an isomer composition of 72% trans and 28% cis isomer.

The two CH3 groups in the intermediate (II-6) and also in the active substances (I) prepared therefrom according to Examples 49-53 are - as indicated - cis-constant according to the 2D NMR measurement.

Starting materials of formula (II):

Example (11-1)

283 g (4.97 mol) of methyl isocyanate are added dropwise with stirring to an ice-cooled solution of 526 g (4.97 mol) of vinyl acetic acid hydrazide in one liter of isopropanol within one hour. The reaction mixture is stirred for a further 30 minutes at room temperature (approx. 20 ° C.) and then 800 ml of water and 800 g of 50% sodium hydroxide solution are added while cooling with ice. The mixture is then heated to 80 ° C. within about 30 minutes and heated under reflux for two hours. The mixture is then concentrated to about half the volume in a water jet vacuum and concentrated with 1 kg. Neutralized hydrochloric acid. The mixture is then concentrated under reduced pressure, the residue is taken up in 1500 ml of N, N-dimethylformamide, the undissolved sodium chloride is separated off by filtration and the filtrate is concentrated again under reduced pressure. The residue is distilled at about 1 mbar.

422 g (55% of theory) of 4-methyl-5- (propen-l-yl) -2,4-dihydro-3H-l, 2,4-triazol-3-one are obtained from the boiling point 140 ° C. (at 1 mbar ), as a cis / trans isomer mixture [which apparently results from double bond isomerization in the course of the reaction, the (propen-3-yl) residue originating from the vinyl acetic acid hydrazide having an isolated, terminal double bond to the (propen-1-yl) residue isomerized with conjugated (cis / trans) double bond].

The product solidifies (melting point: 94 ° C); it consists of 81.5% of the trans isomer and 18.5% of the cis isomer. The isomer mixture can be omitted Recrystallize about twice the amount of ethyl acetate and then provides about 130 g of pure trans isomer (II-1) with a melting point of 112 ° C.

Example (II-2)

H -

A mixture of 178 g (2.0 mol) of 4-methyl-semicarbazide, 10 g of hydroquinone and 250 ml of sulfolane is mixed with 339 g (2.0 mol) of methacrylic anhydride while cooling with ice; the reaction mixture is kept for a further 15 minutes at room temperature (approx.

20 ° C), then mixed with 640 g of 25% sodium hydroxide solution and stirred at 80 ° C for two hours. After cooling to room temperature with conc. Neutralized hydrochloric acid and concentrated under reduced pressure. The residue is extracted hot with toluene. The product crystallizes on cooling the extraction solution; it is isolated by suction.

70 g (25% of theory) of 4-methyl-5- (propen-2-yl) -2,4-dihydro-3H-1,2,4-triazol-3-one with a melting point of 85 ° C. are obtained.

Analogously to the preparation examples (II-1) and (II-2), it is also possible, for example, to prepare the compounds of the formula (II) listed in Table 2 below (for the stereochemical information on R ^2, see the comments on Table 1 above).

Q ¹

H - ^ R ¹

(II)

Examples of use

With regard to the stereochemistry of the test compounds, the comments relating to Table 1 above apply

Example A

Pre-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired level

Concentration.

Seeds of the test plants are sown in normal soil. After about 24 hours, the soil is sprayed with the active ingredient preparation in such a way that the desired amounts of active ingredient are applied per unit area. The concentration of the spray liquor is chosen so that the desired amounts of active compound are applied in 1000 l of water / ha.

After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control.

It means:

0% = no effect (like untreated control) 100%) = total destruction In this test, for example, the compounds according to Preparation Example 3, 4, 6, 9, 10, 12, 13, 17, 19, 20, 22, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33 show , 34, 35, 38, 40, 43, 57 and 59 with largely good tolerance to crop plants such as cotton, barley, corn, rapeseed, sunflower, soybean, wheat and sugar beet, very strong action against weeds.

Table A-3

Active ingredient according to expenditure Baum-Bro-Poa Am-Da-Galin-Stel Manufacturing example no. quantity (g wool mus brosia tura soga laria ai./ha)

(6) 125 95 95 90 90 90 95

Table A-4

Active ingredient according to expenditure Bro-Poa Galin-Matri- Si-Xan

Production example no. quantity (g mus soga caria napis thium ai./ha)

(9) 125 95 95 95 95 90 95

Table A-5

Active ingredient according to WandZucker- Bro- Cy- 'oa Si- Production example no. quantity (g beets mus perus napis ai./ha)

(10) 125 90 90 90 90

section Λ-6

Active ingredient according to expenditure Alope-Bro- PaniPoa Λma- AmGalin-Sola¬

Production example no. quantity (g curus mus cum ranthus brosia soga num ai./ha)

(12) 125 95 95 95 95 95 95 95 95

3 ω

N

ω

O

00

<c

Table A-9

Active ingredient according to expenditure Baum- Alope- Bro- Poa Ama- Ga- Matri- Sola-

(25) 125 95 90 95 90 90 90

Table A- 14

Active ingredient according to expenditure- corn rapeseed soybean tree am- gala- matri-

I Production example no. amount (g - brosia lium soga caria ai./ha) wool

(27) 125 90 90 95 95

Table A- 16

Active ingredient according to expenditure BaumCyno-Poa Ama- Galin- Sola Manufacturing example no. quantity (g wool don ranthus soga num ai./ha)

(31) 125 95 90 90 90 90

Table A- 17

Active ingredient according to effortWeiBaumGalin- Portu- Stel- Manufacturing sample no. amount (g zen wool soga laca laria ai./ha)

(32) 125 10 95 90 90

Table A-18

Active ingredient according to expenditure Baum- Agro- Avena Bro- Lo- Ama- Ga- Sola-

Production example no. quantity (g wool pyron fatua mus lium ranthus lium num ai./ha)

(33) 125 95 95 95 95 95 95 95

(34) 60 95 95 95 90 95 95 90

Example B

Post emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

Concentration.

Test plants which have a height of 5-15 cm are sprayed with the active substance preparation, so that the desired amounts of active substance are applied per unit area. The concentration of the spray liquor is chosen so that in

1000 1 water / ha the desired amounts of active ingredient are applied.

It means:

0% = no effect (like untreated control) 100% = total destruction

In this test, for example, the compounds according to Preparation Example 1, 3, 6, 9, 10, 11, 17, 19, 20, 22, 34, 43, 53, 54, 55 and 59 show with largely good tolerance to crop plants, such as cotton . Wheat and sugar beet, very effective against weeds. TABLE B: Post emergence test / greenhouse

Table B-l:

Active ingredient according to expenditure Alope-Echino-Pani Ama- Cheno- Sola- Viola Preparation example no. quantity (g curus chloa cum ranthus podium num ai./ha)

(3) 60 90 90 100 100 90 95 90

Table B-2

Active ingredient according to expenditureEchino- PaniCas- Ga- SolaManufacturing example no. quantity (g chloa cum sia lium num ai./ha)

(6) 60 95 100 95 95 95

Table B-3

Active ingredient according to expenditure - wheat Ama- Cas- Sola- preparation example no. quantity (g ai./ha) ranthus sia num

(1) 60 95 100 80

Table B-5

Active ingredient according to effort - Wei- Digi- Echino- Sc- Ama- Sola Stel - Manufacturing example no. quantity (g zen taria chloa taria ranthus num laria ai./ha)

(10) 60 80 95 90 95 80

Table B-6

Active ingredient according to effortWei- Digi- Echino- Se- Ama- Sola- StelManufacturing example no. quantity (g zen taria chloa taria ranthus num laria ai./ha)

(1 1) 15 80 90 95 95 90

Table B-7

Active ingredient according to effortWeiZuckerAlope- Se- Ama- Cheno-Da-Ga- Production example no. quantity (g zen beet curus taria ranthus podium tura lium ai./ha)

(17) 125 20 80 95 90 90 95

C _^ ^ Q u "ö3

X> cd H

Table B- 10

Active ingredient according to expenditure Alope-Cype-Echino-Abu- Ama- Datura

1 Production example no. quantity (g curus rus chloa tilon ranthus ai./ha)

(22) 60 90 90 90 90 95 90

Table Bl 3

Active ingredient according to expenditure WeiIope-AmaSolaXan Preparation example no. quantity (g zen curus rant !, us num thium ai./ha)

(53) 60 90 1 0 90 90

Table B- 14

Active ingredient according to Au-WeiAbu- DaSolaViola Xan- i lstcllungsbeispiel-Nr. mcnge (g zen tilon tura num thium ai./ha)

Example C

Podosphaera test (apple) / protective

Solvent: 47 parts by weight of acetone

Emulsifier: 3 parts by weight of alkylaryl polyglycol ether

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

To test for protective activity, young plants are sprayed with the active compound preparation in the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of the apple mildew pathogen Podosphaera leucotricha. The plants are then in the

Greenhouse set up at approx. 23 ° C and a relative humidity of approx. 70%.

Evaluation is carried out 10 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.

In this test, for example, the compounds according to Preparation Examples 3, 24, 26, 29 and 30 show an efficiency of 85% to 100% at an application rate of 100 g / ha each. TABLE C

Podosphaera test (apple) / protective

Active ingredient Application rate of efficiency Active ingredient in ε / ha in%

(3) 100 97

(24) 100 99 TABLE C

(Cont'd) Podosphaera test (apple) / protective

Active ingredient Application rate of effectiveness Active ingredient in g / ha in%

(26) 100 97

(29) 100 89 TABLE C

(Cont'd) Podosphaera test (apple) / protective

(30) 100 85

Example D

Pyricularia test (rice) / systemic

Solvent: 2.5 parts by weight of acetone

Emulsifier: 0.06 part by weight of alkylaryl polyglycol ether #

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

Concentration.

To test for systemic properties, 40 ml of the active ingredient preparation are poured onto common soil in which young rice plants have been grown. 7 days after the treatment, the plants are inoculated with an aqueous spore suspension of Pyricularia oryzae. The plants then remain in a greenhouse at a temperature of 25 ° C. and a relative atmospheric humidity of 100%) until evaluation.

Evaluation is carried out 4 days after the inoculation. 0% means a

Efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.

In this test, for example, the compounds according to Preparation Example 1, 2, 3, 4, 9, 10, 11, 13, 14, 18, 21, 22, 26 and 34 show an efficiency of between 2 mg / 100 cm ² each 10% and 100%. TABLE D

Pyricularia test (rice) / systemic

Active ingredient Application rate of active ingredient in% in mg / 100 cm ²

(3) 100

(1) 100 TABLE D

(Continued)

Pyricularia test (rice) / systemic

Active ingredient Application rate of active ingredient in% in mg / 100 cm ²

(9) 100 TABLE D

(Continued) Pyricularia test (rice) / systemic

Active ingredient Application rate of active ingredient in% in mg / 100 cm ²

(10) 100

(11) 100 TABLE D

(Continued)

Pyricularia test (rice) / systemic

Active ingredient Application rate of active ingredient in% in mg / 100 cm ²

(13) 90

(14) 100 TABLE D

(Continued)

Pyricularia test (rice) / systemic

Active ingredient Application rate of active ingredient in% in mg / 100 cm ²

(18) 70

TABLE D

(Continued)

Pyricularia test (rice) / systemic

Active ingredient Application rate of active ingredient in% in mg / 100 cm ²

(21) 80

CH,

(22) 100 TABLE D

(Continued)

Pyricularia test (rice) / systemic

Active ingredient Application rate of active ingredient efficiency in% in mg / 100 cm ²

(26) 80

(34) 90 Example E

Pyricularia test (rice) / resistance induction

Solvent: 2.5 parts by weight of acetone

Emulsifier: 0.06 part by weight of alkylaryl polyglycol ether

Concentration.

To test for resistance-inducing activity, young rice plants are sprayed with the preparation of active compound in the stated application rate. 5 days after the treatment, the plants are inoculated with an aqueous spore suspension of Pyricularia oryzae. The plants are then placed in a greenhouse at 100% relative atmospheric humidity and a temperature of 25 ° C.

Evaluation is carried out 4 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.

In this test, for example, the compounds according to example 1, 2, 3, 4, 9, 10, 11, 13, 14, 18, 21, 22, 26 and 34 show an efficiency of between 80% and 375 g / ha each. and 100%. TABLE E

Pyricularia test (rice) / resistance induction

(3) 375 100

(1) 375 100 TABLE E

(Continued) Pyricularia test (rice) / resistance induction

(4) 575 90

(9) 375 100 TABLE E

(Continued) Pyricularia test (rice) / resistance induction

(10) 375 80

(11) 575 90 TABLE E

(Continued) Pyricularia test (rice) / resistance induction

(13) 375 90

(14) 80 TABLE E

(Continued) Pyricularia test (rice) / resistance induction

(18) .75 100

(2) 375 100 TABLE E

(Continued) Pyricularia test (rice) / resistance induction

(22) 375 90 HO-

TABLE E

(Continued) Pyricularia test (rice) / resistance induction

(26) 375 100

(34) S75 100

Claims

claims

1. Compounds of the general formula (I),

in which

Q 1 represents oxygen or sulfur,

Q2 represents oxygen or sulfur,

Rl for hydrogen, amino, alkylidene amino or for an optionally substituted radical from the series alkyl, alkenyl. Mkinyl, alkoxy, alkenyloxy, alkylamino, dialkylamino, alkanoylamino, cycloalkyl, cycloalkylalkyl, cycloalkylamino, aryl and arylalkyl,

R2 represents optionally substituted alkenyl and

R ^J for an optionally substituted radical from the series

Alkyl, aralkyl, aryl and heteroaryl,

and salts of compounds of formula (I).

2. Compounds of formula (I) according to claim 1, characterized in that therein Rl for hydrogen, amino, Ci-Cg-alkylidene amino, for C ^ -Cö- optionally substituted by fluorine, chlorine, bromine, cyano, C1-C4-alkoxy, -C -C4-alkylcarbonyl or Cι-C4-alkoxycarbonyl Alkyl, for in each case optionally substituted by fluorine, chlorine and or bromine C2-Cg-alkenyl or C2-Cö-alkynyl, for C \ -Cg-alkyloxy or

C2-C6-alkenyloxy, for in each case optionally substituted by fluorine and / or chlorine Cj-Cg-alkylamino. Di (C 1 -C 4 alkyl) amino or C 1 -C 4 alkyl carbonylamino, each optionally with fluorine. Chlorine, bromine and / or Cj-C4-alkyl substituted C -Cg-cycloalkyl or C3-C6-cycloalkyl-C] -C4-alkyl, or for each optionally by fluorine, chlorine, bromine, cyano. Nitro, C 1 -C 4 -alkyl, trifluoromethyl, C 1 -C 4 -alkoxy and / or C 1 -C 4 -alkoxy-carbonyl-substituted phenyl or phenyl-C 1 -C 4 -alkyl,

R2 represents C2-Cg-alkenyl which is optionally substituted by cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, C 1 -C 4 -alkoxy or C 4 -C 4 -alkoxy-carbonyl, and

R ^{3 stands} for the grouping,

wherein

R 4 and R 5 are the same or different and are hydrogen, fluorine. Chlorine.

Bromine, iodine, nitro, Cj-Cg-alkyl (which may be replaced by fluorine.

Chlorine, bromine, cyano, carboxy, -C-C4-alkoxycarbonyl, Cj-C4-alky - amino-carbonyl, di- (-C-C4-alkyl) -amino-carbonyl. C _] -C4 alkoxy.

-C-C4-Alkyl-carbonyloxy. Cj-C4-alkoxy-carbonyloxy, C1-C4-

Alkylamino-carbonyloxy, Cj-C4-alkylthio, Cι-C4-alkylsulfιnyl, Cj-

C4-alkylsulfonyl, di- (C _] -C4-alkyl) -aminosulfonyl, C3-C5-CVCI0- alkyl or phenyl), for C2-Cg-alkenyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, C1-C4-alkoxycarbonyl or phenyl), for C2-Cg-alkynyl (which is optionally substituted by fluorine, Chlorine, bromine, cyano. C 4 -C 4 -alkoxy-carbonyl or 5 phenyl is substituted) for C 1 -C 4 -alkoxy (which may be substituted by fluorine, chlorine, bromine, cyano, C 1 -C 4 -alkoxy-carbonyl, -C4- Alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfonyl. C j -C ₄ alkylsulfonyl or C3-Cg-cycloalkyl is substituted), for C ₄ -C ₄ -alkylthio (which is optionally substituted by fluorine, chlorine, bromine, Cyano, Cj-C4 alkoxy

10 carbonyl, -C-C4-alkylthio, -C-C4-alkylsulfmyl or C _j -C4-alkylsulfonyl is substituted) for C2-C6-alkenyloxy (which may be substituted by fluorine, chlorine, bromine, cyano or -C-C4-alkoxy -carbonyl is substituted) for C2-Cg-alkenylthio (which may be substituted by fluorine, chlorine, bromine, cyano, nitro, Cι-C3-alkylthio or C1-C4-

15 alkoxy-carbonyl is substituted), C3-Cg-alkynyloxy, C3-C6-alkynyl-thio or for the radical -S (O) -R, where

P

D stands for the numbers 1 or 2 and

20 R for Cj-C4-alkyl (which may be replaced by fluorine. Chlorine.

Bromine, cyano or C1-C4-alkoxy-carbonyl is substituted), C3-C6-alkenyl. C ₃ -C6-Alk_nyl, C \ -C ₄ -alkoxy, -C4- alkoxy-Cι-C4-alkylamino, C ι-C4-alkylamino, di- (C ι-C4-

7 alkyl) amino. Phenyl or represents the radical -NHOR, where

25

7 R for Cj-Ci2-alkyl (which may be replaced by fluorine. Chlorine.

Cyano. C ^ alkoxy, -CC ₄ alkylthio, Cj ^ alkyl sulfinyl. -C-C4-Alkylsulfonyl, C] -C4-alkyl-carbonyl. C1-C4-

Alkoxy-carbonyl. -C-C4-alkylamino-carbonyl or di- (C _] -

30 C4-alkyl) -amino-carbonyl is substituted), for C3-Cg-alkenyl (which is optionally substituted by fluorine, chlorine or bromine), C3-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Cι-C2-alkyl, phenyl-C \ -C2-alkyl (which optionally is substituted by fluorine, chlorine, nitro, cyano, C1-C4-alkyl, C1-C4-alkoxy or Cj-C4-alkoxy-carbonyl), for

Diphenylmethyl or for phenyl (which optionally by fluorine, chlorine, nitro, cyano, CJ-C4-alkyl, trifluoromethyl. C1-C4-alkoxy, Cι-C2-fluoroalkoxy, Cj-C4-alkylthio, trifluoromethylthio or C \ -C4 -Alkoxy-carbonyl is substituted).

R and or R further for phenyl or phenoxy, for -C-C4-alkylcarbonylamino, -C-C4-alkoxy-carbonylamino. C \ -C4 -Akkylamino-carbonylamino, di- (-C-C4-alkyl) -amino-carbonylamino, or for the radical -CO-R, where

R ⁸ for hydrogen, Cj-Cg-alkyl, C3-C ₆ -cycloalkyl, C ^ Cg-

Alkoxy, C3-C-cycloalkoxy, C3-Cg-alkenyloxy, C1-C4-

Alkylthio, C] -C4-alkylamino, -C-C4-alkoxyamino. C1-C4-alkoxy-C] -C4-alkylamino or di- (C \ -C4-alkyl) -amino

(which are optionally substituted by fluorine and / or chlorine),

R and / or R also for trimethylsilyl, thiazolinyl. l, 2,4-oxadiazol-5-yl,

3 -methyl-l, 2,4-oxadiazol-5-yl, U-dioxolan-2-yl, C! -C4-alkylsulfonyloxy, di- (-C-C4-alkyl) -aminosulfonylamino or for the rest

Q

-CH = N-R, where

Q

R for optionally by fluorine, chlorine. Cyano, carboxy, C \ - C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfionyl or C ^ C4-Alkylsulfonyl-substituted Cj-Cg-alkyl, for benzyl optionally substituted by fluorine or chlorine, for optionally substituted by fluorine or chlorine C3-C6-alkenyl or C3-Cg-alkynyl, for optionally substituted by fluorine, chlorine, bromine, C1-C4 - alkyl, C1-C4-alkoxy, trifluoromethyl,

Trifluoromethoxy or trifluoromethylthio substituted phenyl, for optionally substituted by fluorine and / or chlorine Cj-Cg-alkoxy, C3-C6-alkenyloxy, C3-Cg-alkynyloxy or benzyloxy, for amino, C1-C4- alkylam.no. Di- (Cj-C4-alky) amino, phenylamino, C 1 -C 4 -alkyl carbonylamino. C1-C4-

Alkoxy-carbonylamino, -CC-alkyl sulfonylamino or phenylsulfonylamino optionally substituted by fluorine, chlorine, bromine or methyl,

Farther

R ^{3 represents} the rest

wherein

R ¹ ° represents hydrogen or C, -C ₄ alkyl,

R 1 1 and R 12 are the same or different and are hydrogen.

Fluorine, chlorine, bromine, nitro, cyano, Cj-C4-alkyl (which may be substituted by fluorine and / or chlorine), Cj-

C4-alkoxy (which may be replaced by fluorine and / or

Chlorine is substituted), carboxy, C | -C4-alkoxy-carbonyl, Dimethylaminocarbonyl, -C-C4-alkylsulfonyl or di- (C _j - C4-alkyl) -aminosulfonyl are;

Farther

stands,

wherein

R 13 and R 14 are the same or different and are hydrogen,

Fluorine, chlorine, bromine, nitro, cyano, -C ~ C4-alkyl (which is optionally substituted by fluorine and / or chlorine) or C _j -C4-alkoxy (which is optionally substituted by fluorine and / or chlorine), are;

Farther

R ^{3 represents} the rest,

wherein

R and R are the same or different and are hydrogen. Fluorine. Chlorine, bromine. Nitro, cyano, Cj-C4-alkyl (which is optionally substituted by fluorine and / or chlorine), C \ - C4-alkoxy (which is optionally substituted by fluorine and / or chlorine), for Cj ^ -alkylthio, Cι-C4 -Alkyl- sulfinyl or -CC4-alkylsulfonyl (which are optionally substituted by fluorine and / or chlorine), for amino-sulfonyl, mono- (-C-C4-alkyl) -aminosulfonyl, for di- (-C-C4-alkyl) -aminosulfonyl or C j -C4 alkoxycarbonyl or dimethylaminocarbonyl are:

Farther

R ^{3 represents} the rest.

wherein

R 17 and R 18 are the same or different and are hydrogen,

Fluorine, chlorine, bromine, Cj-C4-alkyl (which is optionally substituted by fluorine and / or bromine), -C ~ C4-alkoxy (which is optionally substituted by fluorine and or chlorine), for C] -C4-alkylthio, C \ -C4-Alkylsulfinyl or -C-C4-alkylsulfonyl (which are optionally substituted by fluorine and / or chlorine), or represent di- (Cj-C4-alkyl) - aminosulfonyl;

Farther

R ^{3 represents} the rest,

wherein R, 19 and R, 20 are the same or different and represent hydrogen, fluorine, chlorine, bromine, cyano, nitro, C 1 -C 4 -alkyl (which is optionally substituted by fluorine and / or chlorine), C 4 -C 4 -alkoxy ( which is optionally substituted by fluorine and / or chlorine), C 4 -C 4 -alkylthio. C \ -C4-Alkylsulfιnyl or Cι-C4-alkylsulfonyl (which are optionally substituted by fluorine and / or chlorine), di- (-C-C4-alkyl) -aminosulfonyl, C \ -C4-alkoxy-carbonyl or dimethylamino- carbonvl stand, and

A stands for oxygen, sulfur or the grouping N-T, where

for hydrogen, C1-C4-alkyl (which is optionally substituted by fluorine, chlorine, bromine or cyano), C3-Cg-cycloalkyl, benzyl, phenyl (which is optionally substituted by fluorine, chlorine, bromine or nitro), Cj-C4 -Alkylcarbonyl. C} -C4- alkoxy- carbonyl or di- (-C-C4-alkyl) -aminocarbonyl;

Farther

₂ 1

R ^'

N

R ^{3 stands} for the rest ₂₂ tt- R,

Y

wherein R 21 and R 22 are the same or different and represent hydrogen, C _j -

C4- alkyl, halogen, -C-C4-alkoxy-carbonyl, Cj-C4-alkoxy or Cj-C4-haloalkoxy,

1 Y represents sulfur or the grouping N-R, where

R ^{23 represents} hydrogen or C 1 -C 4 alkyl;

Farther

, 26

₂ 5

R ³ for the rest R

N. stands,

N

, 24th

wherein

R ^{24 represents} hydrogen, Cj-C4-alkyl, benzyl, pyridyl, quinolinyl or phenol.

R 25 for hydrogen, halogen, cyano, nitro, C 1 -C 4 -alkyl (which is optionally substituted by fluorine and / or chlorine), C 1 -C 4 -alkoxy (which is optionally substituted by fluorine and / or

Chlorine is substituted), dioxolanyl or C 4 -C 4 alkoxycarbonyl, and

R for hydrogen. Halogen or C 4 -C 4 -alkyl,

as well as the sodium. Potassium, magnesium, calcium, ammonium, C 1 -C 4 alkyl ammonium, di (C 1 -C 4 alkyl) ammonium, tri (Cι- C4-alkyl) -ammonium-, tetra- (Cι-C4-alkyl) -ammonium, tri- (C _] -C4-alkyl) -sulfonium-, C5- or Cg-cycloalkyl-ammonium- and di- (Cι- C2 -alkyl) -benzyl-ammonium salts of compounds of formula (I).

Compounds of formula (I) according to claim 1 or 2, characterized in that therein

Rl for methyl optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy. Ethyl, n- or i-propyl, for propenyl optionally substituted by fluorine, chlorine or bromine,

Butenyl, propynyl or butynyl, for methoxy, ethoxy, n- or i-propoxy or for allyloxy. represents methylamine, ethylamino, n- or i-propylamino, dimethylamino or diethylamino, or cyclopropyl optionally substituted by fluorine, chlorine, bromine, methyl or ethyl,

R represents ethenyl, propenyl or butenyl which is optionally substituted by cyano, fluorine, chlorine and / or bromine, and

R ^{3 represents} the rest

wherein

R for fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl. Trifluoromethyl, methoxy, ethoxy, n- or i-propoxy. Difluoromethoxy, trifluoromethoxy, 2-chloroethoxy, 2-fluoroethoxy. 2,2-difluoro-ethoxy, 2,2,2-trifluoro-ethoxy, 1, 1,2,2-tetrafluoro-ethoxy, 1,1,2,2,2-pentafluoro-ethoxy, 2-methoxy-ethoxy. Cyclopropylmethoxy, methylthio, ethylthio, n- or i-propylthio, 2-fluoroethylthio, allyloxy, propargyloxy, methylsulfinyl, ethylsulfinyl, methvlsulfonvl, ethylsulfonyl, dimethylaminosulfonyl, diethylaminosulfonyl, N-methoxy-N, phenylaminosulfonyl , Methoxycarbonyl,

Ethoxycarbonyl, n- or i-propoxycarbonyl and

R for hydrogen, fluorine, chlorine, bromine methyl. Ethyl, n- or i-

Propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio or ethylthio;

Farther

wherein

R represents hydrogen,

R for fluorine, chlorine. Bromine, methyl. Methoxy, difluoromethoxy,

Trifluoromethoxy. Ethoxy, methoxycarbonyl, ethoxycarbonyl, methylsulfonyl or dimethylaminosulfonyl and

R ^{12 represents} hydrogen;

Farther R ^{3 represents} the rest,

o what

R represents methyl, ethyl, n- or i-propyl, or

R ^{3 represents} the rest,

^{2 <}

wonn

R24 represents methyl, ethyl, n- or i-propyl, phenyl or pyridyl,

R 5 represents hydrogen, fluorine, chlorine or bromine, and

R 6 represents fluorine, chlorine, bromine, methoxycarbonyl or ethoxycarbonyl.

4. A process for the preparation of compounds of formula (I) according to any one of claims 1-3, characterized in that

(a) triazolin (thi) one of the general formula (II) Q ¹

H - Λ

^N - _, ^{N 'R} ' dl)

N - (R ² in which

Ql, Rl and R have the meaning given in one of claims 1-3,

with sulfonyl iso (thio) cyanates of the general formula (III)

R ³ -S0 ₂ -N = C = Q ² (III)

in which

Q and R ^{3 have} the meaning given in one of claims 1-3,

if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent.

or that one

(b) triazolin (thi) on derivatives of the general formula (IV)

in which Ql, Q, Rl and R2 have the meaning given above and

Z represents halogen, alkoxy, aralkoxy or aryloxy,

with sulfonic acid amides of the general formula (V)

R ³ -SO ₂ -NH ₂ (V)

in which

R ^{3 has} the meaning given above,

if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent,

or that one

(c) triazolin (thi) one of the general formula (II)

Q '

H _^ , NAN. R ¹

(II)

NT

R in which

Ql, Rl and R2 have the meaning given above,

with sulfonic acid amide derivatives of the general formula (VI) R ³ -SO ₂ -NH-CQ ² -Z (VI)

in which

Qj2 and R ^{3 have} the meaning given above and

Z represents halogen, alkoxy, aralkoxy or aryloxy,

or that one

(d) triazolin (thi) one of the general formula (II)

Q '

H . .

IM A R

N

(II)

NT

R 'in which

Ql, Rl and R2 have the meaning given above,

with sulfonic acid halides of the general formula (VII)

R ³ -Sθ2-X (VII)

in which

R ^{3 has} the meaning given above and X represents halogen,

and metal (thio) cyanates of the general formula (VIII)

MQ ² CN (VIII)

in which

Q has the meaning given above and

M represents an alkali metal or an alkaline earth metal equivalent,

if appropriate in the presence of a reaction auxiliary and, if appropriate, in the presence of a diluent,

5. Herbicidal and fungicidal compositions characterized by a content of at least one compound of the formula (I) according to any one of claims 1-3.

6. Use of compounds of general formula (I) according to any one of claims 1-3 to combat unwanted plant growth and / or phytopathogenic fungi.

7. A method for controlling weeds and / or phytopathogenic fungi, characterized in that compounds of the general formula (I) according to one of claims 1-3 are allowed to act on the weeds or fungi or their habitat.

8. A process for the preparation of herbicidal or fungicidal compositions, characterized in that compounds of the general formula (I) according to one of Claims 1-3 are mixed with extenders and / or surface-active agents.

9. Compounds of the general formula (XIV)

in which

R ¹ , R ² and Q ^{1 have} the meanings given in one of claims 1-3 and

A represents hydrogen or the group -CQ ² -Z, wherein

Q ^{2 has} the meaning given in claim 1 and

Z represents halogen, alkoxy, aralkoxy or aryloxy.