DD141899A5 - HERBICIDE MEDIUM - Google Patents

Abstract

The invention relates to new herbicidal compositions. The aim of the invention is to improve the effectiveness and the selectivity of the known compounds. According to the invention, new N-Azolylalkylhalogenacetanilide of the formula i, in which A, r, r1, χ, υ, z and n have the meaning given in the description, used. - Formula i

Description

Herbicidal agents

Field of application of the invention

The present invention relates to novel uT-azolylalkylhalogenoacetanilides and their use as herbicides,

Characteristic of the known technical solutions

It has already become known that 2,6-diethyl-methyl-oxymethyl-chloroacetanilide can be used for selective weed control (see R. Wegler, Chemie der Pflanzenschutz- und Schädlingsbekungsmittel, Volume 5, page 255) Springer-Verlag (1977)). This compound, however, is not always sufficiently safe, especially with respect to dicots, and is not always completely satisfactory in its selectivity.

Object of the invention

The object of the invention is to eliminate these disadvantages.

Presentation of the essence of the invention

The invention has for its object to provide new herbicidal agents.

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There were now as new compounds, the N-Azolylalkyl-haloacetanilides of the formula

N N

(D CO-CHo-Z

in which

, 5 A for oxygen, sulfur or the grouping

> NR ² stands,

R is hydrogen or alkyl,

R ^{1 is} hydrogen, alkyl, haloalkyl, alkenyl,

Alkynyl, cycloalkyl, halogen, optionally

substituted aryl and aralkyl or the group

pations -OR ³ , -SR ³ and MR ² R ³ ,

R ^{2 is} hydrogen, alkyl, or optionally substituted aryl,

R ^{3 is} hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl or optionally substituted

V is arylated aralkyl,

X denotes alkyl,

 Y is alkyl or halogen, Z is halogen and η is the numbers O, 1 or 2,

found.

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Furthermore, it has been found that the N-Azolylalkyl-haloacetanilides of the formula (i) is obtained when N-Azolylalkylaniline of the formula

CH-1 ^ J R ¹ (II)

O η. X) ~ ν _N

in which

A, R, R ¹ ,

X, Y and η are as defined above,

with Kalogenessigsäurechloriden or anhydrides of the formulas

Z-CH ₂ -CO-Cl (purple) or

(Z-CH ₂ -CO) ₂ O (HIb)

in which

Z has the meaning given above,

in the presence of a diluent and optionally in the presence of an acid binding agent.

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In addition, it has been found that the N-Azolylalkylhaloqen acetanilide of the formula (I) have strong herbicidal, especially selective herbicidal properties.

Surprisingly, the N-azolylalkyl-haloacetanilides according to the invention are largely superior to the known 2,6-diethyl-N-methoxymethyl-chloroacetanilide with an equivalent action against monocots in their action against dicotyls. Above all, surprisingly, they show better selectivity in important crop plants than the previously mentioned, previously known compound, which is a highly active substance of the same mode of action. The substances according to the invention thus represent a valuable enrichment of the art.

The N-azolylalkyl-haloacetanilides according to the invention are generally defined by the formula (I). In the formula (I), A is preferably oxygen, sulfur

2 or the grouping -NR *, / wherein R is preferably for

Is hydrogen, straight-chain or branched alkyl having 1 to 4 carbon atoms and aryl having 6 to 10 Γ "\ 20 carbon atoms, in particular phenyl, wherein each of these aryl radicals may be substituted by halogen, alkyl having 1 to 4 carbon atoms, alkoxy with 1 or 2 carbon atoms, alkylthio having 1 or carbon atoms, cyano, nitro and / or haloalkyl having up to 2 carbon atoms and up to 5 identical or different halogen atoms, halogens being in particular fluorine and chlorine, R being preferably in formula (I) is hydrogen, straight-chain or branched alkyl having 1 to 4 carbon atoms, haloalkyl having up to 3 carbon and up to 5 identical or

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various halogen atoms, halogens being in particular fluorine and chlorine, by way of example trifluoromethyl, furthermore preferably alkenyl and alkynyl having 2 to 4 carbon atoms, cycloalkyl having 5 to 7 carbon atoms and halogen, in particular fluorine, chlorine or bromine. R is furthermore preferably aryl having 6 to 10 carbon atoms, in particular phenyl, where each of these aryl radicals may be substituted by halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 or 2 carbon atoms, alkylthio having 1 or 2 carbon atoms, cyano, nitro and or haloalkyl having up to 2 carbon atoms and up to 5 identical or different halogen atoms, halogens being in particular fluorine or chlorine and trifluoromethyl being mentioned as an example of haloalkyl. R is furthermore preferably aralkyl having 6 to 10 carbon atoms in the aryl moiety and 1 to 4 carbon atoms in the alkyl moiety, in particular benzyl, where each of these aralkyl moieties in the aryl moiety may be substituted by halogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 or 2 carbon atoms, Alkylthio having 1 or 2 carbon atoms, cyano, nitro and / or ketoalkyl having up to 2 carbon atoms and up to 5 identical or different halogen atoms, halogens being in particular fluorine or chlorine and trifluoromethyl being mentioned as an example of haloalkyl. In addition, R stands

3 3 2 3 2 for the groupings -OR, -SR and -NR R, in which R is preferably those radicals which have already been mentioned above as being preferred for this radical, R in these groupings is preferably hydrogen,

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straight-chain or branched alkyl having 1 to 4 carbon atoms, halogenoalkyl having 3 carbon atoms and up to 5 identical or different halogen atoms, halogens being in particular fluorine and chlorine, by way of example trifluorine is thy I, furthermore preferably alkenyl and alkynyl with 2 to 4 carbon atoms, cycloalkyl having 5 to 7 carbon atoms and aralkyl having 6 to 10 carbon atoms in the aryl moiety and 1 to 4 carbon atoms in the alkyl moiety, especially benzyl, each of these aralkyl moieties in the aryl moiety may be substituted by halogen, alkyl of 1 to 4 carbon atoms , Alkoxy having 1 or 2 carbon atoms, alkylthio having 1 or 2 carbon atoms, cyano, nitro and / or haloalkyl having up to 2 carbon atoms and up to 5 identical or different halogen atoms, wherein halogens are in particular fluorine or chlorine and trifluoromethyl as an example of haloalkyl specifically mentioned

 In the formula (I), X is preferably straight-chain or branched alkyl having 1 to 4 carbon atoms. Y in formula (I) is preferably straight-chain or branched alkyl having 1 to 4 carbon atoms or for the halogens fluorine, chlorine and bromine. Z is preferably chlorine, bromine and iodine; the index η stands for the numbers 0,1 or 2.

As examples of N-Azolylalkylhalogenacetanilide of formula (I) according to the invention may be mentioned in detail:

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2,6-diethyl-N- /] 5-methyl-1,3,4-oxadiazol-2-yl-methyl) 7-chloroacetanilide 2-ethyl-6-methyl-N- _/! f (5-methyl-1,3,4-oxadiazol-2-yl-ethyl-1-chloroacetanilide 2,6-dimethyl-N- / 15-methyl-1,3,4-oxadiazol-2-yl-methyl) 7-

chloroacetanilide. *

2-tert-butyl-N-Z "(5-methyl-1,3,4-oxadiazol-2-yl-methyl) 7-

chloroacetanilide:

2-chloro-6-tert.-butyl-N- / T (5-methyl-1,3,4-oxadiazol-2-yl- • jO inethyl) 7-chloroacetanilide 2-chloro-3-methyl-N- ^ (5-methyl-1 , 3,4-oxadiazol-2-ylmethyl) 7-chloroacetanilide 2-chloro-6-methyl-N - ^ (5-methyl-1 _/ 3,4-oxadiazol-2-ylmethyl) 7 '

chloroacetanilide ^ 5 2-chloro-6-isopropyl-NZ "(5-methyl-1 _/ 3,4-oxadiazol-2-ylmethyl) j'-chloroacetanilide 2-isopropyl-N - (5-methyl-1, 3,4-oxadiazol-2-ylmethyl) 7-chloroacetanilide 2-ethyl-6-isopropyl-N - / "(5-methyl-1,3,4-oxadiazol-2-ylmethyl) -7-chloroacetanilide 2-bromo -6-tert-butyl-N- _i! f (5-methyl-1, 3, 4-oxadiazol-2-yl-methyl) 7-chloroacetanilide 2-bromo -6-isopropyl-N - / - (5-methyl-1,3,4-oxadiazol-2- ylmethyl) 7-chloroacetanilide 2,3-dimethyl-N - / "(5-methyl-1,3,4-oxadiazol-2-yl-methyl) 7-chloroacetanilide, S-dimethyl-N- ^ S-methyl- i, 3,4-oxadiazol-2-ylmethyl) J7-chloroacetanilide 2 _f 6-diethyl-N- (5-ethyl-1,3,4-oxadiazol-2-yl-methyl) 7-chloroacetanilide 2-ethyl -6-methyl-N - / (5-ethyl-1, 3,4-oxadiazol-2-yl-methyl) 7- * chloroacetanilide

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2,6-Dimethyl-N - / (5-ethyl-1,3,4-oxadiazol-2-ylmethyl) .7-chloroacetanilide 2-tert-butyl-N-ZK5-ethyl-1,3 , 4-oxadiazol-2-ylmethyl) J-chloroacetanilide 2-chloro-6-tert-butyl-N- [pi] (5-ethyl-1,3,4-oxadiazol-2-ymethyl) -7-chloroacetanilide 2 , 6-diethyl-N- (5-isopropyl-1,3,4-oxadiazol-2-yl-methyl-7-chloroacetanilide 2-ethyl-6-methyl-N - / (5-isopropyl-1,3, 4-oxadiazol-2-yl-methyl-1-chloroacetanilide 2,6-dimethyl-N- / ~ (5-isopropyl-1,3,4-oxadiazol-2-ylmethyl] L7-chloroacetanilide 2-tert-butyl-N - / "(5-isopropyl-1,3,4-oxadiazol-2-yl-ethyl) _7-chloroacetanilide 2/6-diethyl-N-15-n-propyl-1,3,4-oxadiazol-2-yl methyl) 7-chloroacetanilide 2-ethyl-6-methyl-N- / 15-n-propyl-1 _/ 3 _/ 4-oxadiazol-2-ylmethyl) .7-chloroacetanilide 2,6-dimethyl-N- £ I5-n -propyl-l, 3,4-oxadiazol-2-ylmethyl) _7-chloroacetanilide 2-tert-butyl-N- £ (5-n-propyl-1,3,4-oxadiazol-2-ylmethyl ) L7 chloracetaniiid 2,6-diethyl-N- _i T (5-phenyl-1,3 _/ 4-oxadiazol-2-yl-methyl) 7-chloroacetanilide 2, 6-diethyl-NZ "(5-phenyl-1 , 3, 4-oxadiazol-2-ylmethyl) 7-c chloroacetanilide 2-ethyl-1-6-methyl-N-ZX 5-trichloromethyl-1,3,4-oxadiazol-2-ylmethyl) 7-chloroacetanilide 2,6-dimethyl-N- / 1-trichloromethyl-1 _f 3 , 4-oxadiazol-2-ylmethyl) I7-ichloracetanilid

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_ Q mm

2-tert-butyl-N- {{5-trichloromethyl-1, J, 4-oxadiazol-2-yl-methyl-chloro-acetanilide} 2-chloro-6-tert-butyl-N - (5-trichloro-1-ethyl-1 , 3,4-oxadiazol-2-ylmethylL7-chloroacetanilide 2,6-diethyl-NZ "(5-trifluoromethyl-1,3,4-oxadiazol-2-yl)

methyl] L7-chloroacetanilide f

2-ethyl-6-methyl-N-ε (5-trifluoro-ethyl-1 _# 3,4-oxadiazol-2-ylmethyl) -chloroacetanilide 2,6-dimethyl-N- _i- T (5-trifluoromethyl-1, 3 _/ 4-oxadiazol-2-yl-methyl-1-chloroacetanilide 2-tert-butyl-N- / 15-trifluoromethyl-1,3,4-oxadiazol-2-ylmethyl-O-chloroacetanilide 2-chloro-6-tert.-butyl N- / ~ (5-trifluoromethyl-1,3,4-oxadiazol-2-ylmethyl) _7-chloroacetanilide 2 _# 6-diethyl-N - / (5-chloromethyl-1,3,4-oxadiazole) 2-yl-methyl-7-chloroacetanilide 2-ethyl-6-methyl-N - ^ (5-chloromethyl-1,3,4-oxadiazol-2-ylmethyl) J7-chloroacetanilide 2,6-dimethyl-N- / 15-chloromethyl -i, 3,4-oxadiazol-2-ylmethyl) _7-chloroacetanilide 2,6 ~ diethyl-N - / (5-chloro-1,3,4-oxadiazol-2-yl-methyl) 7-chloroacetanilide 2- Ethyl 6-methyl-N - / (5-chloro-1,3 _/ 4-oxadiazol-2-ylmethyl) 7-chloroacetanilide 2,6-Dimethyl-N- £ 5-chloro-1,3,4 -oxadiazol-2-ylmethyl) 7-chloroacetanilide 2 , 6-diethyl-N- (5-bromo-1,3,4-oxadiazol-2-yl-methyl) 7-chloroacetanilide 2-ethyl-6-methyl -N- £ T 5- bromo-1,3,4-oxadiazol-2-yl-raethyl) J-chloroacetanilide, 2,6-diethyl-N-, n is 5-methoxy-1,3, 4-oxad iazol-2-yl-methyl) 7-chloroacetanilide

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2-ethyl-6-methyl-N- (N- (5-methoxy-1,3,3,4-oxadiazol-2-ylmethyl) -7-chloroacetanilide 2 _# 6-dimethyl-NZ "(5-methoxy-1,3,4 -oxadiazol-2-yl-methyl-7-chloroacetanilide 2-tert-butyl-N - / (5-methoxy-1,3,4-oxadiazol-2-yl-methyl-7-chloroacetanilide 2,6-diethyl-N- "(5-methylthio-1,3,4-oxadiazol-2-ylmethyl) J-chloroacetanilide 2-ethyl-6-methyl-N- / ~ (5-methylthio-1,3,4-oxadiazole-2-yl) ylmethyl)! 7-chloroacetanilide 2, o-dimethyl-N-zn 5-methylthio-1,3,4-oxadiazol-2-yl-methyl) 7-chloroacetanilide 2-tert-butyl-N- £ "(5- Methylthio-1,3,4-oxadiazol-2-ylmethyD1-chloroacetanilide 2,6-Diethyl-N- £ 1 (5-dimethylamino-1,3,4-oxadiazol-2-ylmethyl) -chloroacetanilide 2-ethyl-6 -methyl-N - / * (5-dimethylamino-1,3 _/ 4-oxadiazol-2-ylmethyl) -chloroacetanilide 2,6-diethyl-N- / T; 5-benzyl-1,3,4-oxadiazol-2 yl-methylL7-chloroacetanilide 2-ethyl-6-methyl-N- / 75-benzyl-1,3,4-oxadiazol-2-ylmethyl) J7-chloroacetanilide 2,6-diethyl-N - / * (5-methyl- 1 _/ 3,4-oxadiazol-2-yl-methyll7-chloroacetanilide 2-ethyl-6-methyl-N- _i T (5-methyl-1,3,4-thiadiazol-2-ylmethyl 1-chloro-acetanilide 2,6-dimethyl-N - / - (5-methyl-1,3,4-thiadiazol-2-yl-methyl L7-chloroacetanilide 2-tert. Butyl N - / - (5-methyl-1,3,3,4-thiadiazol-2-ylmethyl) 7-chloroacetanilide 2-Chloro-6-tert. -butyl-N- / f (5-methyl-i, 3, 4-thiadiazol-2-yl-methyl) J7-chloroacetanilide, 2-chloro-3-methyl-NZ (5-methyl-1,3,4-thiadiazole -2-chloroacetanilide ylir.üthyDT'-2-chloro-6-methyl-N- / l5-raethyl-1,3 _# 4-thiadiazol-2-ylmethyl) 7-chloroacetanilide, 2-chloro-6-isopropyl-NZ ( 5-methyl-1 _/ 3,4-thiadiazol-2-ylmethyljj'-chloroacetanilide

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2-Isopropyl-i; 5-methyl-1,3,4-thiadiazol-2-yl-methyl L7-chloroacetanilide 2-ethyl-6-isopropyl-N - / (5-methyl-1,3,4-thiadiazole -2-ylmethyl) J7-chloroacetanilide 2-bromo-6-tert-butyl-N ~ / "(5-methyl-1,3,4-thiadiazol-2-ylmethyl) _7-chloroacetanilide 2-bromo-6-isopropyl -N- "(5-methyl-1 / 3,4-thiadiazol-2-ylmethyl-2-chloroacetanilide 2,3-dimethyl-N- / f (5-methyl-1,3,4-thiadiazol-2-yl) methyll7-chloroacetanilide 2, 5-dimethyl-N- / 15-methyl-1,3,4-thiadiazol-2-ylmethyl) J-chloroacetanilide 2,6-diethyl-N- _i O5-aethyl _# 1,3 _# 4-thiadiazol-2-yl-methyl) L7-chloroacetanilide 2-ethyl-6-methyl-N- ^ 5-ethyl-1,3, 4-thiadiazol-2-chloroacetanilide ylmethylU-2,6-dimethyl-N- £ (5-ethyl-1,3, 4-thiadiazol-2-yl-methyl) 7-chloroacetanilide 2-tert. butyl-N- ^ Ti 5-ethyl-1,3,4-thiadiazol-2-yl-methyl ) 7-chloroacetanilide 2-chloro-6-tert-butyl-N- / 15-ethyl-1, 3,4-thiadiazol-2-ylmethylO-chloroacetanilide 2 _r 6-diethyl-NZ- {5-isopropyl-1, 3,4-thiadiazol-2-ylmethyl) 7-chloroacetanilide 2-ethyl-6-methyl-N- (5-isopropyl-1,3,4-thiadiazol-2-ylmeth yDJ-chloroacetanilide 2,6-dimethyl-N- ^ 5-isopropyl-l _f 3,4-thiadiazol-2-yl-methyl-7-chloroacetanilide 2-tert-butyl-N- £ T 5-isopropyl-1,3, 4-thiadiazol-2-ylmethyl) 7-chloroacatanilide

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2,6-diethyl-N / (5-n-propyl-1,3,4-thiadiazol-2-ylmethyl) L7-chloroacetanilide 2-ethyl-6-methyl-N- / T (5-n-propyl) 1,3,4-thiadiazQ2-2-ylmethy1 )] - chloroacetanil 2,6-dimethyl-N- / j [5-n-propyl-1,3,4-thiadiazol-2-ylmethyl-7-chloroacetanilide 2-tert. Butyl N - / - (5-n-propyl-1,3,4-thiadiazol-2-y 1-methyl-U-chloroacetanilide 2,6-diethyl-N - / - (5-phenyl 1-1, 3, 4 thiadazole-2-y 1-methyl chloroacetanilide,

^, 6-diethyl-N- (5-phenyl-1,3,4-thiadiazol-2-yl-methyl) 7-chloroacetanilide 2-ethyl-6-ethyl-N- / Γ -5-trichloromethyl-1, 3,4-thiadiazol-2-ylmethyl) 7-chloroacetanilide \ 2,6-dimethyl-NZ "(5-trichloromethyl-1,3,4-thiadiazol-2-ylmethyl) 7" chloroacetanilide 2-tert. Butyl-N- (5-trichloromethyl) -1,3,4-thiadiazol-2-yl-methyl) J-chloroacetanilide 2-chloro-6-tert-butyl-N- (5-trichloromethyl) -1,3,4 -thiadiazol-2-yl-methyl-7-chloroacetanilide 2,6-diethyl-N - / (5-trifluoromethyl-1,3,4-thiadiazol-2-ylmethyl) -7-chloroacetanilide 2-ethyl-6-methyl-N ZT (5-trifluoromethyl-1,3,4-thiadiazol-2-ylmethyl) 7-chloroacetanilide 2,6-Dimethyl-N-E (5-trifluoromethyl-1,3,4-thiadiazole-2-yl) ylmethyDJ-chloroacetanilide 2-tert.-butyl-1NZ "(5-trifluoromethyl-1,3,4-thiadiazol-2-ylmethyl) 7-chloroacetanilide 2-chloro-6-tert.-butyl-N- / 1 [5 trifluoromethyl-1, 3,4-thiadiazol-2-ylmethyl) J-chloroacetanilide 2,6-diethyl-N- (5-chloromethyl-1,3,4-thiadiazol-2-ylmethyl) 7- chloroacetanilide

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2-ethyl-6-methyl-N, -I-5-chloromethyl-1,3,4-thiadiazol-2-yl-methyl) 7-chloroacetanilide, 2,6-dimethyl-N - / (5-chloromethyl-1-1, 3,4-thiadiazol-2-y 1-methyl) _7.-chloroacetanilide 2,6-diethyl-N- / f (5-chloro-1,3,4-thiadiazol-2-ylmethyl) -7-chloroacetanilide 2 ethyl-6-methyl-N- / a5-chloro-1,3,4-thiadiazol-2-ylmethyl) _7-chloroacetanilide

2,6-Dimethyl-N - / "(5-chloro-1,3,4-thiadiazol-2-yl-methyl) L7- • JO chloroacetanilide 2,6-diethyl-N- / f (5-bromo-1 , 3,4-thiadiazol-2-ylmethyl) 7-chloroacetanilide 2-ethyl-6-methyl-N- / n [5-bromo-1 _# 3,4-thiadiazol-2-ylmethyl-U-chloroacetanilide 2,6- Diethyl-N - / "(5-methoxy-1 _/ 3,4-thiadiazol-2-yl-methyl-7-chloroacetanilide 2-ethyl-6-methyl-N - / (5-methoxy-1,3,4-thiadiazole -2-ylmethyl-chloroacetanilide 2,6, -dimethyl-N-Zl5-methoxy-1,3,4-thiadiazol-2-yl-methyl-7-chloroacetanilide 2-tert-butyl-N- / D (5-methoxy -1,3,4-thiadiazol-2-ylmethyl) 7 "chloroacetanilide 2 _/ 6-diethyl-NZ" {5-ethylthio-1,3 _/ 4-thiadiazol-2-ylmethyl) 17-chloroacetanilide 2-ethyl 6-methyl-N-> T (5-methylthio-1,3,4-thiadiazol-2-yl-methyl) 7-chloroacetanilide 2,6-dimethyl-1-N-> 5-methylthio-1, 3,4- thiadiazol-2-ylmethyl) 7-chloroacetanilide 2-tert-butyl-N- ₎ T (5-methylthio-1,3,4-thiadiazol-2-ylmethyl) -chloroacetanilide 2,6-diethyl-N- £ (5 -diinethylamino-1,3,4-thiadiazol-2-ylmethyl) 7-chloroacetanilide

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2-ethyl-6-methyl-N- £ "(5-dimethylamino-1,3,4-thiadiazol-2-yl-methyl) -chloroacetanilide j ^r 2,6-diethyl-N - /" (5-benzyl- 1, 3,4-thiadiazol-2-ylmethyl) 7-chloroacetanilide 2-ethyl-6-methyl-N- (5-benzyl-1,3,4-thiadiazol-2-ylmethyl-U-chloroacetanilide 2,6- Diethyl 1-N-ZT (5-ethylthio-1,3,4-thiadiazol-2-yl-methyl-7-chloroacetanilide

2-ethyl-6-methyl-N- _/ f (5-ethylthio-1,3,4-thiadiazol-2-yl-yl-methyl-chloroacetanilide 2,6-dimethyl-N- / ~ (5-ethylthio-1,3-yl) 4-thiadiazol-2-yl-methy117-chloroacetanilide 2-tert-butyl-N- (5-ethylthio-1,3,4-thiadiazol-2-ylmethyl) -7-chloroacetanil id 2,6-diethyl-N-Zr (5 ~ allylthio-1,3,4-thiadiazol-2-yl-methyl) L7-chloroacetanilide

2-Ethyl-6-methyl-N- {5-allylthio-1,3,4-thiadiazol-2-yl-methyl-1-chloroacetanilide 2 _# 6-dimethyl-NZ "(5-allylthio-1,3 _/ 4-thiadiazole -2-yl-methyl) 7-chloroacetanilide

2-tert-butyl-N-t5-allylthio-1,3,4-thiadiazol-2-ylmethyl)! 7-chloroacetanilide 2,6-diethyl-N- £ 1 [5-benzylthiO'-1,3, 4-thiadiazol-2-ylmethyl) 17-chloroacetanilide 2-ethyl-6-methyl-N- (5-benzylthio-1,3,4-thiadiazol-2-yl-methyl) 7-chloroacetanilide 2,6-dimethyl- N- £ I 5-benzylthio-1,3,4-thiadiazol-2-ylmethyl) 7-chloroacetanilide 2-tert. -Buty 1-NZ "(5-benzylthio-1,3,4-thiadiazol-2-ylmethyl-6-chloroacetanilide 2,6-diethyl-N-α5-isopropylthio-1,3,4-thiadiazol-2-ylmethyl) 7 -chloroacetanilide

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2-ethyl-6-methyl-NZ "(5-isopropylthio-1,3,4-thiadiazol-2-ylmethyl) _7-chloroacetanilide 2,6-dimethyl-N - /" (5-isopropylthio-1, 3,4-thiadiazol-2-ylmethyl-7-chloroacetanilide 2-tert-butyl-N- (5-isopropylthio-1,3,4-thiadiazol-2-ylmethyl) -7-chloroacetanilide 2,6-diethyl-N-Z13 , 4-dimethyl-1,2,4-triazol-S-yl-methylV-chloroacetanilide 2-ethyl-6-methyl-N- (3,4-dimethyl-1,2,4-triazol-5-ylmethyl) -j -chloroacetanilide 2 , 6-Dimethy 1-N- / 1 (3,4-dimethyl-1,1,2,4-triazole-5-yl-1-methyl-117-chloroacetanilide 2-tert-butyl-N-if ( 3,4-dimethyl-1,2,4-triazol-5-ylmethyl-7-chloroacetanilide 2,6-diethyl-N- (3-ethyl-4-methyl-1,2,4-triazol-5-ylmethyl) - chloroacetanilide 2-ethyl-6-methyl-NZ "(3-ethyl-4-methyl-1,2,4-triazol-5-yl-methyl) 7-chloroacetanilide 2,6-dimethyl-N- / T (3 ethyl-4-methyl-1,2,4-triazol-5-ylmethyl) Z7-chloroacetanilide 2-tert-butyl-N-ZT (3-ethyl-4-methyl-1,2,4-triazole-5- ylmethyl-chloro-acetanilide 2,6-diethyl-N-ε (3-methyl-4-phenyl-1,2,4-triazol-5-ylmethyl) ω-chloroacetanilide 2-ethyl-6-methyl-N-ε ( 3-methyl-4 -phenyl-1,2,4-triazol-5-ylmethyl) 7-chloroacetanilide 2,6-dimethyl-N - / - (3-methyl-4-phenyl-1,2,4-triazol-5-ylmethyl7 -chloroacetanilide 2-tert-butyl-N-Zl3-methyl-4-phenyl-1,2,4-triazol-5-ylmethyl) 7-chloroacetanilide 2,6-diethyl-N- / T (3-methylmercapto -4-methyl-1,2,4-triazol-5-yl-methyl) J7-chloroacetanilide

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2-ethyl-6-methyl-N- (3-methylmercapto-4-methyl-1,2,4-triazol-5-yl-methyl) 7-chloroacetanilide 2,6-dimethyl-N - / (3 methylmercapto-4-methyl-1, 2,4-triazol-S-yl-methyl-yl-chloroacetanilide 2-tert-butyl-NZp-methyl-atercaptc-4-methyl-1,2,4-triazol-5-yl-methyl) 7-chloroacetanilide 2,6-diethyl-N- (3-methoxy-4-methyl-1,2,4-triazol-5-ylmethyl] L7-chloroacetanilide 2-ethyl-6-methyl-N - / - {3 -methoxy-4-methyl-1,2,4-triazol-5-yl-m-ethyl) L7-chloroacetanilide 2,6-dimethyl-N- / 13-methoxy-4-methyl-1,2,4-triazole-5 -ylmethy1 \ J chloroacetanilide

2-tert-butyl-N- (3-methoxy-4-methyl-1,2,4-triazol-5-yl-methyl) -y-chloroacetanilide 2,6-diethyl-N- (3-methylmercapto 4-pheny1-1,2,4-triazol-5-ylmethyl) 7-chloroacetanilide 2-ethyl-5-methyl-N- £ T 3-methylmercapto-4-phenyl-1,2,4-triazole 5-ylmethyl) 7-chloroacetanilide 2,6-Dimethyl-N- ^ 3-methylmercapto-4-phenyl-1,2,4-triazol-S-yl-methyl-D-chloroacetanilide 2-tert-Butyl-1-N- fi S -methylmercapto ^ -phenyl-1,2,4-triazole S-yl-methyDj'-chloroacetanilide 2,6-diethyl-N - / (3-methoxy-4-phenyl-1,2,4-triazole -5-ylmethyl) -7-chloroacetanilide 2-ethyl-6-methyl-N- (T (3-methoxy-4-phenyl-1,2,4-triazol-5-yl-methyl) -y) -chloroacetanilide 2.6 Dimethyl-N- / j (3-methoxy-4-phenyl-1,2,4-triazol-5-ylmethyl) -7-chloroacetanilide 2-tert-butyl-N-n3-methoxy-4-phenyl-1 , 2, 4-triazol-5-yl methyl-chloroacetanilide ^ and the corresponding bromoacetanilides ^ 7

Le A 18 690

• 2 1 08 4 8 -17-

2,6-diethyl-N- (1,3,4-oxadiazol-2-ylmethyl) -chloroacetanilide 2-ethyl-6-methyl-N- (1,3,4-oxadiazol-2-ylmethyl) -chloroacetanilide 2,6-Dimethyl-N- (1,3,4-oxadiazol-2-yl-methyl) -chloroacetanilide 2-tert-butyl-N- (1,3,4-oxadiazol-2-yl-methyl ) -chloroacetanilide 2,6-Diisopropyl-N- (1,3,4-oxadiazol-2-yl-methyl) -chloroacetanilide 2,6-Diisopropyl-N-> T5-methyl-1,3,4-oxadiazole-2 -ylethyl-7-chloroacetanilide 2-Chloro-6-tert-butyl-N- (1,3,4-oxadiazol-2-yl-methyl) -chloroacetanilide 2-Chloro-6-methyl-N- (1,3 , 4-oxadiazol-2-yl-methyl) -chloroacetanilide 2, 3-dimethyl-N- (1,3,4-oxadiazol-2-yl-methyl) -chloroacetanilide

2, 5-dimethyl-N- (1,3,4-oxadiazol-2-yl-methyl) -chloroacetanilide, 2,6-diethyl-N- (5-tert-butyl-1,3,4-oxadiazol-2 -ylmethyl) -chloroacetanilide 2-ethyl-6-methyl-N- (5-tert-butyl-1,3,4-oxadiazol-2-ylmethyl) -chloroacetanilide 2,6-diisopropyl-N- (5- methyl-1,3,4-thiadiazol-2-ylmethyl) -chloroacetanilide 2, 6-diethyl-N- (5-methyl-1,3,4-thiadiazol-2-ylmethyl) -chloroacetanilide, 2,6-diethyl -N- (1,3,4-thiadiazol-2-yl-methyl) -chloroacetanilide

2-Xthyl-6-methyl-N- (1,3,4-thiadiazol-2-yl-methyl) -chloroacetanilide

Le A 18 690

210848

2,6-dimethyl-N- (1,3,4-thiadiazol-2-yl-methyl) -chloroacetanilide

2-tert-butyl-N- (1,3,4-thiadiazol-2-yl-methyl) -chloroacetanilide

2,6-diisopropyl-N- (1,3,4-thiadiazol-2-yl-methyl) -chloroacetanilide

2-chloro-6-methyl-N- (1,3,4-thiadiazol-2-yl-methyl) -chloroacetanilide

2-chloro-6-tert. butyl N- (1,3-thiadiazol-1-yl-methyl) chloroacetanilide

2,3-dimethyl-N- (1,3,4-thiadiazol-2-yl-methyl) -chloroacetanilide

2,5-dimethyl-N- (1,3,4-thiadiazol-2-yl-methyl) -chloroacetanilide

• 2,6-diethyl-N- (4-methyl-1,2,4-triazol-5-yl-methyl) -chloroacetanilide

2,6-dimethyl-N- (4-methyl-l, 2,4-triazol-5-yl-methyl) -chloroacetanilide

2-Kthyl-6-methyl-N- (4-methyl-1,2,4-triazol-5-yl-methyl) -chloroacetanilide

2-tert-butyl-N- (4-methyl-1,2,4-triazol-5-yl-methyl) -chloroacetanilide

2, 6-Diisopropyl-N- (4-methyl-1,2,4-triazol-5-yl-methyl) -chloro-acetanilide

and the corresponding bromoacetanilides.

Le A 18 690

21 0848 -19 -

Using 2,6-diethyl-N- (3-methylthio-4-methyl-l, 2,4-triazol-5-yl-methyl) -aniline and Qiloracetylcftlorid as starting materials, the reaction sequence can be represented by the following formula scheme :

C ₂ H ₅

C ₂ H ₅

N N

j i

\ N - ^ SCH ₃ CH ₃

C ₂ H ₅

L-CO-CH, Cl

HCl

N-N

.CH ₂ Π ή

_Ν N bueh ₅

\ CH ₃ C ₂ H ₃ \

CO-CH ₂ Cl

The N-Azolylalkylaniline required as starting materials in carrying out the process according to the invention are generally defined by the formula (II). In this formula, A, R, R, X, Y and η are preferably those radicals which are already in connection with the description of the compounds of the formula (I) according to the invention preferably for

2 3 these radicals have been mentioned. The radicals R and R are also preferably those radicals which have already been described in connection with the description of the invention

2 Substances of the formula (I) preferably for the radicals R and

R were called.

Le A 18 690

21 084

As examples of the N-Azolylalkylaniline of formula (II) may be mentioned:

2,6-diethyl-N- (5-methyl-l _f 3,4-oxadiazol-2-yl-methyl) -aniline 2-ethyl-e-methyl-N- (5-methyl-1,3,4- oxa-diazol-2-yl-methyl) -aniline 2,6-dimethyl-N- (5-methyl-1,3-4-oxadiazol-2-ylmethyl) -aniline

2-tert-butyl-N- (5-methyl-l, 3,4-oxadiazol-2-yl-methyl) -aniline

2-chloro-6-tert-butyl-N- (5-methyl-1,3,4-oxadiazol-2-ylmethyl) -aniline 2-chloro-3-methyl-N- (5-methyl-1,3-d , 4-oxadiazol-2-ylmethyl) -aniline 2.-Chloro-S-Diene-Uyl-N- (5-methyl-3fi-4-oxadiazol-2-yl-methyl) -aniline 2-Chloro-O -IsOPrOPyI-N- (5-methyl-1,3,4-oxadiazol-2-ylmethyl) -aniline 2-isopropyl-N- (5-methyl-1,3,4-oxadiazol-2-ylmethyl) - aniline 2-Ae ^ yl-O-ISOPrOPyI-N- (5-methyl-1,3,4-oxadiazol-2-ylmethyl) -aniline 2-bromo-6-tert-butyl-N- (5-methyl -l, 3,4-oxadiazol-2-ylmethyl) -aniline 2-bromo-6-isopropyl-N- (5-methyl-1,3,4-oxadiazol-2-ylmethyl) -aniline 2,3-dimethyl- N- (5-methyl-1,3,4-oxadiazol-2-ylmethyl) aniline

, 2,5-dimethyl-N- (5-methyl-l, 3 _f 4-oxadiazol-2-yl-methyl) -aniline

2,6-diethyl-N- (5-ethyl-l, 3,4-oxadiazol-2-yl-methyD-aniline

2-ethyl-6-methyl-N- (5-ethyl-l, 3,4-oxadiazol-2-ylmethyl) aniline

Le A 18 690

2 1084 8

2,6-Dimethyl-N- (5-ethyl-l, 3,4-oxadiazol-2-ylmethyl) aniline

2-tert-butyl-N- (5-ethyl-l, 3,4-oxadiazol-2-yl-methyl) -aniline

2-Chloro-6-tert-butyl-N- (5-ethyl-1, 3,4-oxadiazol-2-ylmethyl) -aniline 2,6-diethyl-N- (5-isopropyl-1, 3,4 oxadiazol-2-yl-methyl) -aniline

2-ethyl-6-methyl-N- (5-isopropyl-1, 3,4-oxadiazol-2-yl-.lambda..sub.10-methyl) -aniline 2,6-dimethyl-N- (5-isopropyl-1,3, 4-oxadiazol-2-ylmethyl) aniline 2-tert-butyl-N- (5-isopropyl-l, 3,4-oxadiazol-2-ylmethyl) aniline 2, 6-diethyl-N- (5-n -propyl-l, 3,4-oxadiazol-2-ylmethyl) -aniline

2-ethyl-6-methyl-N- (5-n-propyl-1,1,4-oxadiazol-2-yl-methyl) -aniline 2,6-dimethyl-N- (5-n-propyl-1, 3,4-oxadiazol-2-yl-methyl) -aniline

2-tert-butyl-N- (5-n-propyl-l, 3,4-oxadiazol-2-ylmethyl) aniline

2,6-diethyl-N- (5-phenyl-1,3,4-oxadiazol-2-yl-methyl) -aniline 2,6-diethyl-N- (5-phenyl-1,3,4-oxadiazole) 2-yl-methyl) -aniline

2-ethyl-6-methyl-N- (5-trichloromethyl-1,1,4-oxadiazol-2-ylmethyl) -aniline 2,6-dimethyl-N- (5-trichloromethyl-1,3,4- oxadiazol-2-ylmethyl) -aniline 2-tert-butyl-N- (5-trichloromethyl-1,3,4-oxadiazol-2-yl-me-thyl) -aniline in 2-chloro-6-tert-butyl N- (5-trichloromethyl-1,3,4-oxadiazol-2-ylmethyl) -aniline 2,6-diethyl-N- (5-trifluoromethyl-1,3,4-oxadiazol-2-ylmethyl) - aniline

Le A 18 690

210848

2-ethyl-6-methyl-N- (5-trifluoromethyl-1,3,4-oxadiazole

2-yl-methyl) -aniline

2,6-Dimethyl-N- (5-trifluoromethyl-1,3,4-oxadiazol-2-y 1-methyl) -aniline 2-tert-butyl-N- (5-trifluoromethyl-1,3,4- oxadiazol-2-

yl-methyl) -aniJLin

2-chloro-6-tert-butyl-N- (5-trifluoromethyl-1,3,4-oxadiazol-2-yl-methyl) -aniline 2,6-diethyl-N- (5-chloromethyl-1,3-d , 4-oxadiazol-2-ylmethyl) -aniline 2-ethyl-6-methyl-N- (5-chloromethyl-1,3,4-oxadiazole)

2-yl-methyl) -aniline

2,6-Dimethyl-N- (5-chloromethyl-1,3,4-oxadiazol-2-ylmethyl) -aniline 2,6-diethyl-N- (5-chloro-l, 3,4-oxadiazol-2 yl-methyl) -

aniline. 2-ethyl-6-methyl-N- (5-chloro-1,4-oxadiazol-2-yl)

methyl) aniline

2,6-Dimethyl-N- (5-chloro-1,3,1-oxadiazol-2-yl-methyl) -aniline 2,6-diethyl-N- (5-bromo-1,3,4-oxadiazole) 2-yl-methyl) -aniline 2-ethyl-6-methyl-N- (5-bromo-1,1,4-oxadiazol-2-ylmethyl) aniline 2,6-diethyl-N- (5-methoxy -l, 3,4-oxadiazol-2-yl-methyl) aniline

2-ethyl-6-methyl-N- (5-methoxy-1,3,4-oxadiazol-2-yl)

methyl) aniline

2,6-Dimethyl-N- (5-methoxy-1,3,10-oxadiazol-2-yl-methyl) -aniline 2-tert-butyl-N- (5-methoxy-1,3,4-oxadiazole) 2-yl

methyl) aniline

2,6-diethyl-N- (5-methylthio-l, _3,4-O-2-yl xodiazol

methyl) aniline

2-ethyl-6-methyl-N- (5 ~ methylthio-l, 3,4-oxadiazol-2-yl-methyl) -aniline

Le A 18 690,

210848

2,6-Dimethyl-N- (5-methylthio-l, 3,4-oxadiazol-2-ylmethyl) -aniline 2-tert-butyl-N- (5-methylthio-l, 3,4-oxadiazole-2 -ylmethyl) -aniline 2,6-diethyl-N- (5-dimethylamino-1, 3,4-oxodiazol-2-yl)

methyl) aniline

2-ethyl-6-methyl-N- (5-dimethylamlno-l, 3,4-oxadiazol-

2-yl-methyl) -aniline

2,6-diethyl-N- (5-benzyl-l, 3,4-oxadiazol-2-yl-methyl) -aniline

2-ethyl-6-methyl-N- (5-benzyl-l, 3,4-oxadiazol-2-yl

methyl) aniline

2,6-diethyl-N- (5-ethylthio-l, 3,4-thiadiazol-2-yl-methyl) -aniline 2-ethyl-6-methyl-N- (5-ethylthio-1, 3,4- thiadiazole -2-yl-

methyl) aniline

2,6-Dimethyl-N- (5-ethylthio-l, 3,4-thiadiazol-2-yl-methyl)

aniline

2-tert-butyl-N- (5-ethylthio-l, 3,4-thiadiazol-2-ylmethyl) aniline

2-chloro-o-tert-butyl-N- (5-methyl-1,3,4-thiadiazol-2-yl-ethyl) -aniline 2-chloro-3-methyl-N- (5-methyl-1,3-d , 4-thiadiazol-2-ylrethyl) aniline 2-chloro-5-r: ethyl-N- (5-methyl-l, 3 _f 4-thiadiazol-2-ylr.etr.yl) aniline 2-Chior- c-isopropyl-N- (5-methyl-l, 3,4-thiadiazol-2-ylnethyl) aniline

2-isopropyl-N- (5-methyl-l, 3,4-thiadiazol-2-yl-methyl) -aniline

2-ethyl-6-isopropyl-N- (5-methyl-1,3,4-thiadiazol-2-yl-diethyl) -aniline 2-ergo-6-tert-butyl-N- (5-methyl-1, 3,4-thiadiazol-2-ylcethyl) aniline

Le A 18 690

2 10848 -24-

2-Bromo-6-isopropyl-N- (5-ethyl-1, 3,4-thiadiazol-2-ylmethyl) -aniline 2,3-dimethyl-N- (5-ethyl-1,3 ', 4-thiadiazole -2-ylmethyl) aniline 2,5-Dimethyl-N- (5-methyl-l, 3,4-thiadiazol-2-ylmethyl) aniline 2,6-diethyl-N- (5-ethyl-1 , 3,4-thiadiazol-2-ylmethyl) aril in 2-ethyl-6-niethyl-N- (5-ethyl-1,3,4-thiadiazol-2-yl-ethyl) -aniline 2 , 6-dimethyl-N- (5-ethyl-1,3,4-thiadiazol-2-ylmethyl) -aniline 2-tert-butyl-N- (5-ethyl-1,3,4-thiadiazole) 2-yl-methyl) -

aniline _#

2-chloro-6-tert. butyl-N- (5-ethyl-1,3,4-thiadiazol-2-yl-ethyl) -aniline .2,6-diethyl-N- (5-isopropyl-l, 3,4-thiadiazole-2-one yl-methyl) ar. * "L ¹ T.

2-ethyl-6-methyl-N- (5-isopropyl-l, 3,4-thiadiazol-2-yl-ethyl) -aniline 2,6-Dinethyl-N- (5-isopropyl-1: 3,4 -thiadiazol-2-yl-ethyl) -aniline 2-tert-butyl-N- (5-isopropyl-l, 3,4-thiadiazol-2-yl-ethyl) -aniline 2,50-diethyl-N- (5- n-propyl-l, 3,4-thiadiazol-2-ylmethyl) -aril in 2-ethyl-6-methyl-N- (5-n-propyl-l, 3,4-thiadiazole-2 -y1 = eThyl) -aniline

2,6-Dimethyl-N- (5-n-propyl-l, 3,4-thiadiazol-2-yl-methyl) 30'aniline 2-er-t-ethyl-N- (5-n-butyl) propyl-l, 3,4-thiadiazol-2-yl-ethyl) -aniline 2,6-diethyl-N- (5-phenyl-1,3,4-thiadiazol-2-ylmethyl) aniline 2,5-diethyl- N- (5-phenyl-l, 3,4-thiadiazol-2-ylmethyl) aniline

Le A 18

210848

2-ethyl-6-ethyl-N- (5-trichloromethyl-1,3,4-tiazadiazol-2-yl-methyl) -aniline

2,6-Diethylethyl N- (5-trichloromethyl-1,3,4-thiadiazol-2-yl-.

ethyl) -aniline 2-tert-butyl-N- (5-trichloromethyl-1,3,4-thiadiazol-2-yl-methyl) -aniline

2-Chloro-6-tert-butyl-N- (5-trichloromethyl-1,3,4-thiadiazol-2-yl-methyl) -aniline

2,6-diethyl-N- (5-trifluoromethyl-l, 3,4-thiadiazol-2-ylmethyl) -aniline

2-ethyl-6-ethyl-N- (5-trifluoromethyl-1,3,4-thiadiazol-2-yl-methyl) -aniline

2,6-dichloro-N- (5-trifluoromethyl-1,3,4-thiadiazol-2-yl-ethyl) -aniline 2-tert-eutyl-N- (5-trifluoromethyl-1,314-thiadiazole-2 -yl-r.ethyl) -aniline

2-chloro-o-tert. -butyl-N- (5-trifluoromethyl-]., 3,4-thiadia2ol-2-yl-methyl) -aniline

2, c-Diethyl-N- (5-chloro-ethyl-l, 3,4-thiadiazol-2-yl-ethyl) -aniline

2-ethyl-6-chloroethyl- N - (5-chloromethyl-1,3,4-thiadiazol-2-yl-r.ethyl) -aniline

2, 6-ZL- ethyl-N- (5-chloromethyl-1,3,4-thiadiazol-2-yl)

r.ethyl) -aniline 252,6-diethyl-N- (5-chloro-l, 3,4-thiadiazol-2-ylmethyl) -

2-Aer ': iyl-6-r.ethyl-N- (5-chloro-l, 3,4-thiadiazol-2-yl- za- thy 1) - to i 1 in

2, β-3-ethyl-N- (5-chloro-1, 3,4-thiadiazol-2-yl-methyl) -aniline

2,6-diethyl-N- (5-bromo-1,3,4-thiadiazol-2-yl-methyl) -aniline 2-ethyl-6-methyl-N- (5-bromo-l _f 3,4- thiadiazol-2-yl-methyl) aniline.

2,6-diethyl-N- (5-methoxy-l, 3,4-thiadiazol-2-ylmethyl) aniline

Le A 18 690

21084 8

2-ethyl-6-methyl-N- (5-methoxy-l, 3,4-thiadiazol-2-yl-ethyl) -aniline, 2,5-dinyl-N- (5-methoxy-l, 3,4- thiadiazol-2-y 1-methyl) aniline 2-tert. Butyl N- (5-methoxy-l, 3,4-thiadiazol-2-ylrr-ethyl) -aniline 2, o-diethyl-N- (5-methylthlo-l, 3,4-thiadiazole-2 -ylzethyl) -aniline 2-Ac-c: -. yl-6-N-N- (5-methylthio-l, 3,4-thiadiazol-2-yl-ethyl) -aniline 2,6-dichloroethyl -N- (5-methylthio-l, 3,4-thiadiazol-2-yl

met: hyl) aniline

2-tert. Butyl N- (5-methylthio-l, 3,4-thiadiazol-2-yl-η, -ethyl) -aniline 2, δ-diethyl-N- (5-dimethylamino-l, 3,4-thiadiazole-2 -ylne-hyl) -aniline 2-Ae-hyl-6-r.ethyl-N- (5-dimethylamino-l, 3,4-thiadiazole)

2-yl-r.ethyl) aniline

2,5-diethyl-N- (5-tenzyl-l, 3,4-thiadiazol-2-ylmethyl) s.niline

2-ethyl-6-methyl-N- (5-benzyl-1,3,4-thiadiazol-2-yl)

rr.c-thyl) aniline

2, O-diethyl-N- (5-ethylthio-1, 3,4-thiadiazol-2-ylmethyl)

25 Z-Asxy-e-E

R.5-hyl) aniline

2, i -Dir.ethyl-N- (5-ethylthio-l, 3,4-thiadiazol-2-yl-aethyl) -

aniline

2-t-Butyl ~ rü.-N- (5-ethylthio-l, 3,4-thiadiazol-2-yl-Cethyl> ar.iiir.

2,6-diethyl-N- (5-allylthio-l, 3,4-thiaaiazol-2-yl = iethyl) -

2-Ateryl-6-ethyl-N- (5-allylthio-l, 3,4-thiadiazol-2-yl-methyl) -aniline ^ .5-dir. Ethyl-N- (5-allylthio-1 , 3,4-thiadiazol-2-yl-Cethyl) -ar.ilin

2 - C £ r -.- 3utyl-N- (5-allylthio-l, 3,4-thiadiazol-2-yl-sethyl) -anilir.

Le A 18 690

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2,6-diethyl-N- (5-benzylthio-l3-4-thiadiazol-2-ylmethyl) -aniline 2-ethyl-6-methyl-N- (5-benzylthio-l, 3,4-thiadiazole) 2-ylmethyl) -aniline 2,6-Dinethyl-N- (5-benzylthio-l, 3,4-thiadiazol-2-ylmethyl) -aniline 2-tert-butyl-N- (5-benzylthio-1H , 3,4-thiadiazol-2-ylmethyl) -aniline 2,6-diethyl-N- (5-isopropylthio-l, 3,4-thiadiazol-2-ylmethyl) -aniline 2-ethyl-methyl N- (5-isopropylthio-l, 3,4-thiadiazol-2-ylmethyl) -aniline 2,6-Dimethyl-N- (5-isopropylthio-l, 3,4-thiadiazol-2-ylmethyl) -aniline 2-tert-butyl-N- (5-isopropylthio-l, 3,4-thiadiazol-2-yl-Dethyl) aniline 2,6-di ethyl-N- (3,4-dimethyl-l, 2, 4-triazol-5-yl-methyl) -aniline 2-ethyl-6-methyl-N- (3 ₁ 4-dimethyl-l, 2,4-triazol-5-yl-methyl) aniline 2,6-dimethyl N- (3,4-dimethyl-1,2,4-triazol-5-yl-methyl) -aniline 2-tert-butyl-N- (3,4-dimethyl-1,2,4-triazole) 5-yl-methyl) -aniline 2,6-diethyl-N- (3-ethyl-4-methyl-1,2,4-triazol-5-yl-methyl) -anilino-ethyl-S-methyl-N - (3-ethyl-4-methyl-l, 2,4-triazol-5-ylmethyl) -aniline 2,6-Diaethyl-N- (3-ethyl-4-methyl-1,2,4-triazole 5-yl-methyl) -aniline 2-tert-butyl-N- (3-ethyl-4-methyl-1,2,4-triazol-5-yl-methyl) -aniline 2,6-diethyl-N- (3-methyl-4-phenyl-1,2,4-triazol-5-ylmethyl) -aniline 2-ethyl-6-methyl-N- (3-ethyl-4-phenyl-1,2,4- triazol-5-yl-ethyl) -aniline 2,6-Diniethyl-N- (3-methyl-4-phenyl-1,2,4-triazol-5-ylmethyl) -

aniline ',.

Le A 18

210848

2-tert-butyl-N- (3-methyl-4-phenyl-1 _f 2,4-triazol-5-yl

methyl) aniline *.

2,6-diethyl-N- (3-methylmercapto-4-methyl-1,2,4-triazol-5-ylmethyl) -aniline 2-ethyl-6-methyl-N- (3-methylmercapto-4-methyl) l, 2,4-triazol-5-yl-methy1) aniline

2,6-Dimethyl-N- (α-methylmercapto-1-methyl-1,2,4-triazol-5-yl-methyl) -aniline

2-tert-butyl-N- (3-methylmercapto-4-methyl-l, 2,4-triazol-5-yl-methyl) -aniline

2,6-diethyl-N- (3-methoxy-4-methyl-l, 2,4-triazol-5-yl-methyl) -aniline

2-ethyl-6-methyl-N- (3-methoxy-4-methyl-1,2,4-triazol-5-ylmethyl) -aniline 2,6-dimethyl-N- (3-methoxy-4-methyl- l, 2,4-triazol-5-yl-methyl) -aniline

* 2-t§rt. Butyl N- (3-methoxy-4-methyl-1,2,4-triazole-5-ylmethyl) -aniline

2,6-diethyl-N- (3-methylmercapto-4-phenyl-l, 2,4-triazol-5-ylmethyl) aniline

2-ethyl-5-methyl-N- (3-methylmercapto-4-phenyl-l, 2,4-triazol-5-yl-methyl) -aniline

2,6-dimethyl-N-O-methylmercapto-1-phenyl-1,2,4-triazol-5-ylmethyl) -aniline 2-tert-butyl-N- (3-methylmercapto-4-phenyl-1,2-diol) , 4-triazol-5-methyl) -aniline

2,6-diethyl-N- (3-methoxy-4-phenyl-l, 2,4-triazol-5-yl-methyl) -aniline

2-ethyl-6-methyl-N- (3-methoxy-4-phenyl-l, 2,4-triazol-5-ylmethyl) aniline

2,6-dimethyl-N- (3-methoxy-4-phenyl-l, 2,4-triazol-5-yl-methyl) -aniline

2-tert-butyl-N- (3-methoxy-4-phenyl-l, 2,4-triazol »5-yl-methyl) -aniline

Le A 18 690

2,6-Diisopropyl-N- (5-methyl-1,3,4-oxadiazol-2-ylmethyl) -aniline 2-chloro-6-methyl-N- (5-methyl-1,3,4-oxadiazole) 2-ylmethyl) -aniline 2,6-diethyl-N- (1,3,4-oxadiazol-2-ylmethyl) -aniline 2,6-dimethyl-N- (1,3,4-oxadiazole-2-yl) yl-methyl) -aniline 2-A'-ethyl-6-methyl-N- (1,3,4-oxadiazol-2-yl-methyl) -aniline 2-tert-butyl-N- (1,3,4 -oxadiazol-2-ylmethyl) -aniline 2,6-Diisopropyl-N- (1,3,4-oxadiazol-2-ylmethyl) -aniline 2-chloro-6-tert-butyl-N- (1, 3,4-oxadiazol-2-ylmethyl) -aniline 2,6-diethyl-N- (5-methyl-1,3,4-thiadiazol-2-yl-methyl) -aniline 2-ethyl-6-methyl N- (5-methyl-1,3,3,4-thiadiazol-2-ylmethyl) -aniline 2,6-dimethyl-N- (5-methyl-1,3,4-thiadiazol-2-ylmethyl) - aniline 2-tert-butyl-N- (5-methyl-1,3,4-thiadiazol-2-yl-methyl) -aniline 2,6-diethyl-N- (1,3,4-thiadiazole-2-one) yl-methyl) -aniline 2,6-Diisopropyl-N- (1,3,4-thiadiazol-2-yl-methyl) -aniline 2-ethyl-6-methyl-N- (1,3,4-thiadiazole) 2-yl-methyl) -aniline

2,6-Dimethyl-N- (1,3,4-thiadiazol-2-yl-methyl) -aniline 2-Chloro-6-tert-butyl-N- (1,3,4-thiadiazol-2-yl -methyl) -aniline 2-tert-butyl-N- (1,3,4-thiadiazol-2-yl-methyl) -aniline

Le A 18

210848

The N-Azolylalkylaniline of formula (II) are not yet known. You get them when you

a) anilines of the formula

(IV)

in which

X, Y and η are as defined above,

with azole derivatives of the formula

y N N

Hal - CH H. Ji R ¹

in which A, R and R ^{1 have} the abovementioned meaning and

Shark stands for chlorine or bromine,

in the presence of an acid binder such as potassium or sodium carbonate, and in the presence of an inert organic solvent, such as dimethylformamide or toluene, at temperatures between 20 and 16O ° C, preferably an excess of aniline of the formula (IV) is used (see also Production examples), or

Le A 18 690

2 1 084 8 - si -

b) hydrazine derivatives of the formula

CH - CO - NH - NH ₂

(VI)

in which

R, X, Y and η have the abovementioned meaning with isocyanates or mustard oils of the formula

R ² -N = C = B (VII)

in which

B stands for oxygen or sulfur and

R ^{2 has} the meaning given above,

in the presence of an organic solvent, such as an alcohol, ether or hydrocarbon, at temperatures between 0 and 80 ° C, the resulting compounds of the formula

CH-CO-NH-NH-CB-NHR ²

IT (VIII)

^N H

in which

B, R, R ²

X, Y and η are as defined above,

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2! 084 8

cyclized in the presence of a strong base, such as sodium or potassium hydroxide solution, and in the presence of a solvent such as ethanol or water at temperatures between 20 and 100 ⁰ C and the resulting triazolones or triazolothiones of the formula

(Ix)

in which B, R, R ²

X, Y and η are as defined above,

with halides of the formula

Shark - R * (X)

in which

Shark stands for chlorine or bromine and

R * represents the radicals of substituent R ³ , hydrogen being excluded,

in the presence of a strong base, such as sodium hydroxide solution, and in the presence of an inert organic solvent, such as toluene or methylene chloride, at temperatures between 20 and 80 ⁰ C, wherein also phase transfer can be catalyzed and with other alkylating reagents, such as dimethyl sulfate, can be used ( compare also production examples), or

Le A 18 690

2 1 0848 - 33 -

c) hydrazine derivatives of the formula (VI) with formic acid or acid chlorides or acid anhydrides of the formulas

R ⁵ -CO-Cl (XIa)

or.

(R ⁵ -CO-) ₂ O (XIb)

in which

R is alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, optionally substituted aryl or optionally substituted aralkyl is in the presence of an inert organic solvent such as an ether, hydrocarbon or halohydrocarbon, reacted at temperatures between 0 ⁰ C and 50 ° C and the resulting compounds the formula

CH-CO-NH-NH-CO-R ⁵

in which

R, R, X,

Y and η are as defined above,

either with diphosphorus pentasulfide in a manner known per se (compare Chem. Ber., 3J2, 797 (1899) and J. prakt. Chemistry ££, 145 (1904) cyclized to thiadiazole derivatives, or also in a known manner with customary dehydrating reagents Oxadiazole derivatives reacted (see Elderfield, Heterocyclic Compounds, Vol 7 (1961)) or

d) hydrazine derivatives of the formula (VI) with nitriles of the formula

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210848

R ⁶ -C = N- '

in which

R is alkyl, haloalkyl or optionally

substituted aryl stands

converts in a conventional manner to triazole derivatives (ver same Chem.Ber. £ 6, 1064 (1963)), or

e) hydrazine derivatives of the formula (VI) with imino ethers of the formula

F? - C χ HCl (XIV)

^{X is} OR ⁷

in which

R ^{5 is} alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, optionally substituted aryl or optionally

substituted aralkyl and R is methyl or ethyl,

in a conventional manner, under reflux and in the presence of an inert organic solvent such as ethanol, to form oxadiazole derivatives, or

f) the anilines of the formula (IV) with azole aldehydes of the formula

H "^ ^A '

si (XV)

in which

R ^{1 has} the meaning given above,

Le A 18 690

2 1 0848 - ³⁵ -

in the presence of an inert organic solvent, such as toluene, at temperatures. Between 80 and 12O ⁰ C and the resulting compounds of the formula

• 5 in which

A, R ¹ , X, Y and η have the abovementioned meaning, reduced in a generally known manner; for example, by reaction with complex hydrides, such as sodium borohydride, optionally in the presence of a polar organic solvent, such as methanol, at temperatures between 0 and 8O ⁰ C.

The starting materials of the formula (IV) are generally known compounds of organic chemistry. Examples which may be mentioned are: 2-methylaniline, 2-ethylaniline, 2-propylaniline, 2-isopropylaniline, 2-butylaniline, 2-isobutylaniline, 2-sec-butylaniline, 2-tert-butylaniline, 2,6-dimethylaniline, 2, 6-diethylaniline, 2-ethyl-6-methylaniline, 2,6-diisopropylaniline, 2,3-dimethylaniline, 2,4-dimethylaniline, 2,5-dimethylaniline, 2-ethyl-3-methylaniline, 2-ethyl-4- methylaniline, 2-ethyl-5-methylaniline, 2,4,6-trimethylaniline, 2,4,5-trimethylaniline, 2-ethyl-4,6-dimethylaniline, 2,6-diethyl-4-methylaniline, 2,6- Diisopropyl-4-methylaniline, 2-chloro-6-methylaniline, 5-chloro-2-methylaniline, 3-chloro-2-methylaniline, 4-chloro-2-methylaniline, 2-chloro-6-tert-butylaniline ,

The starting materials of the formula (V) are known or can be prepared by generally customary and known heterocyclic syn-

Le A 18 690

210848

(See, inter alia, Helv. Chim. Acta 5J., 1979ff (1972); Chem. Ber. 3, p. 79, 7ff (1899) and 96, 1049ff (1963)). Examples include:.

2-chloromethyl-5-methyl-l, 3,4-oxadiazole 2-chloromethyl-5-ethyl-l, 3,4-oxadiazole 2-chloroethyl-5-isopropyl-l, 3,4-oxadiazole 2-chloroethyl-5 trifluoromethyl-1,3,4-oxadiazole 2-chloromethyl-5-trichloromethyl-1, 3,4-oxadiazole 2-chloromethyl-5-allyl-1, 3,4-oxadiazole 2-chloromethyl-S-cyclohexyl-1, 3,4-Oxadiazole 2-Chloromethyl-5-benzyl-1,3,4-oxadiazole 2-Chloromethyl-5-methoxy-1,3,4-oxadiazole 2-Chloromethyl-5-allyloxy-1,3,4-oxadiazole

2-Chloromethyl-5- (2-fluorobenzyloxy) -1,3,4-oxadiazole 15_ 2-Chloromethyl-5-methylthio-1, 3,4-oxadiazole 2-Chloromethyl-5-allylthio-1, 3,4-oxadiazole 2-chloromethyl-5- (2-fluorobenzylthio) -1,3,4-oxadiazole 2- (1-chloroethyl) -5-methyl-1,3,4-oxadiazole 2- (1-chloroethyl) -5-ethyl-1, 3,4-oxadiazol-1-chloromethyl-S-methyl-1H-thiadiazole 2-chloromethyl-5-ethyl-1,3,4-thiadiazole 2-chloro-1-yl-S-isopropyl-1,3,4-thiadiazole 2-chloromethyl-5-trifluoromethyl-1,3,4-thiadiazole 2-Chloromethyl-5-trichloromethyl-1,3,4-thiadiazole 2-chloroethyl-5-allyl-l, 3,4-thiadiazole 2-chloromethyl-5 -cyclohexyl-l, 3,4-thiadiazole 2-chloromethyl-5-benzyl-l, 3,4-thiadiazole

2-chloromethyl-5-methoxy-l, 314-thiadiazole i

2-chloromethyl-5-allyloxy-l, 3,4-thiadiazole 2-chloromethyl-5- (2-fluorobenzyloxy) -1,3,4-thiadiazole 2-chloromethyl-5-methylthio-l, 3,4-thiadiazole 2 -Chloromethyl-5-allylthio-l, 3,4-thiadiazole 2-chloromethyl-5- (2-fluorobenzylthio) -1,3,4-thiadiazole 2- (1-chloroethyl) -5-methyl-1,3 4-thiadiazole 2- (1-chloroethyl) -5-ethyl-l, 3,4-thiadiazole

Le A 18 690

2-Chloromethyl-5-methyl-1,3,4-triazole 2-Chloromethyl-5-ethyl-1,3,4-triazole 2-Chloromethyl-5-isopropyl-1,3,4-triazole 2-chloromethyl-5 trifluoromethyl-1,3,4-triazole 2-chloromethyl-5-trichloromethyl-1,3,4-triazole 2-chloromethyl-5-allyl-l, 3,4-triazole 2-chloromethyl-5-cyclohexyl-1, 3,4-triazole 2-chloromethyl-5-benzyl-l, 3,4-triazole '2-chloromethyl-5-methoxy-l, 3,4-triazole 2-chloromethyl-5-allyloxyA, 3,4-triazole 2 -Chloromethyl-5- (2-fluorobenzyloxy) -1,3,4-triazole 2-chloromethyl-5-methylthio-l, 3,4-triazole 2-chloromethyl-5-allylthio-l, 3,4-triazole 2- Chloromethyl-5- (2-fluorobenzylthio) -1,3,4-triazole 2- (1-Chloroethyl) -5-methyl-1,3,4-triazole 2- (1-Chloroethyl) -5-ethyl-1 , 3,4-triazole 2-chloromethyl-l, 5-dimethyl-l, 3,4-triazole 2-chloromethyl-5-ethyl-1-methyl-l, 3,4-triazole 2-chloromethyl-5-isopropyl 1-methyl-1,3,4-triazole 2-Chloromethyl-1-methyl-5-trifluoromethyl-1,3,4-triazole 2-Chloromethyl-1-methyl-5-trichloromethyl-1,3,4-triazole 2 -Chloromethyl-5-allyl-1-methyl-1,3,4-triazole 2-chloromethyl-5-cyclohexyl-1-methyl-1,3,4-triazole 2 -Chloromethyl-5-benzyl-1-methyl-1,3,4-triazole 2-chloromethyl-5-methoxy-1-methyl-1,3,4-triazole 2-chloromethyl-5-allyloxy-1-methyl-1 , 3,4-triazole 2-chloromethyl-5- (2-fluorobenzyloxy) -1-methyl-l, 3,4-triazole 2-chloromethyl-5-methylthio-1-methyl-1,3,4-triazole Chloromethyl-5-allylthio-1-methyl-1,3,4-triazole 2-chloromethyl-5- (2-fluorobenzylthio) -1-methyl-1,3,4-triazole 2- (1-chloroethyl) -1, 5-dimethyl-l, 3,4-triazole 2- (1-chloroethyl) -5-ethyl-1-methyl-1,3,4-triazole

Le A 18 690

2 1 084 8

The starting materials of the formula (VI) are not yet known. However, they can be prepared by known methods by using known esters (see, inter alia, DT-OS 2 350 944 and 2 513 730) of the formula

(XVII)

in which R, X, Y

and η are as defined above and

R is methyl or ethyl,

reacted with hydrazine hydrate preferably in the presence of an organic solvent such as ethanol, dioxane or dimethylformamide, at temperatures between 20 and 12O ° C (see also Preparation Examples).

Examples include: 2,6-diethylanilino-acetic acid hydrazide. 2,6-Dimethylanilinoacetic acid hydrazide 2,4,6-Trimethylanilinoacetic acid hydrazide 2-Ethyl-6-methylanilinoacetic acid hydrazide α- (2,6-diethylanilino) -propionic acid hydrazide α- (2,6 Dimethylanilino-propionic acid hydrazide α- (2,4,6-trimethylanilino) -propionic acid hydrazide fc- (2-ethyl-6-methylanilino-propionic acid hydrazide

The starting materials of the formulas (VII), (X), (XIa), (XIb), (XIII) and (XIV) are generally known compounds of organic chemistry.

Le A 18 690

210848

In the compounds of the formulas (XIa) and (XIb) R preferably represents straight-chain or branched alkyl having 1 to 4 carbon atoms, halogenoalkyl having up to

3 carbon and up to 5 identical or different halogen atoms, halogens being especially fluorine and chlorine, by way of example trifluoromethyl, furthermore preferably alkenyl and alkynyl having 2 to 4 carbon atoms, cycloalkyl having 5 to 7 carbon atoms and halogen, in particular fluorine , Chlorine or bromine. R is furthermore preferably aryl having 6 to 10 carbon atoms, in particular phenyl, where each of these aryl radicals may be substituted by halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 or 2 carbon atoms, cyano, nitro and / or haloalkyl having up to 2 carbon atoms and up to 5 identical or different halogen atoms, halogens being in particular fluorine or chlorine and trifluoromethyl being mentioned as an example of haloalkyl. R furthermore preferably represents aralkly having 6 to 10 carbon atoms in the aryl moiety and 1 to 4 carbon atoms in the alkyl moiety, in particular benzyl, where each of these aralkyl moieties in the aryl moiety may be substituted by halogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 or 2 carbon atoms Alkylthio having 1 or 2 carbon atoms, cyano, nitro and / or haloalkyl having up to 2 carbon atoms and up to 5 identical or different halogen atoms, halogens being in particular fluorine or chlorine and trifluoromethyl being mentioned as an example of haloalkyl.

Le A 18 690

210848

In the compounds of formula (XIII), R is preferably alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms and 1 to 5 halogen atoms, or optionally of

Halogen, alkyl having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, alkoxy having 1 to 4 carbon atoms and / or nitro-substituted aryl having 6 to 10 carbon atoms, in particular phenyl.

In the imino ethers of the formula (XIV) R ⁵ preferably represents those radicals which have already been mentioned as preferred in connection with the description of the compounds of the formula (XI a) and (XI b).

Le A 18 690

The starting materials of the formula (XV) or their preparation are also known (compare Elderfield, Heterocyclic Compounds, Vol.7 (l96l) and Advances in Heterocyclic Chemistry, Vol.9 (1968)).

The also for the reaction according to the invention as starting materials to be used haloacetic acid chlorides or anhydrides are generally defined by the formulas (IIIa) and (IIIb). In these formulas, Z is preferably chlorine, bromine and iodine.

The haloacetic acid chlorides and anhydrides of the formulas (IIIa) and (IIIb) are well known compounds of organic chemistry. Examples which may be mentioned are: chloroacetyl chloride, bromoacetyl chloride, iodoacetyl chloride and the corresponding anhydrides.

Suitable diluents for the reaction according to the invention are preferably inert organic solvents. These include preferably ketones, such as diethyl ketone, especially acetone and methyl ethyl ketone; Nitriles, such as propionitrile, in particular acetonitrile; Ethers, such as tetrahydrofuran or dioxane; aliphatic and aromatic hydrocarbons, such as petroleum ether, benzene, toluene or xylene; halogenated hydrocarbons, such as methylene chloride, carbon tetrachloride, chloroform or chlorobenzene; and esters, such as ethyl acetate.

If appropriate, the process according to the invention can be carried out in the presence of acid binders (hydrogen chloride acceptors). As such, all customary acid binding agents can be used. These preferably include organic bases, such as tertiary amines, for example triethylamine, or 'such as pyridine; Further, inorganic bases, such as alkali metal hydroxides and alkali metal carbonates.

Le A 18 690

21084 8

The reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, one works between 0 and 120 ⁰ C, preferably between 20 and 100 ⁰ C.

When carrying out the process according to the invention, preference is given to using 1 mol of the compound of the formula (II) to 1.5 mol of haloacetylating agent and from 1 to 1.5 mol of acid binder. The isolation of the compounds of formula (i) is carried out in the usual manner.

The active compounds according to the invention influence plant growth and can therefore be used as defoliants, desiccants, haulm killers, germ inhibitors and in particular as weed killers. Weeds in the broadest sense are understood to mean all plants which grow up on roots where they are undesirable. Whether the substances according to the invention act as total or selective herbicides essentially depends on the amount used.

The active compounds of the invention may e.g. used in the following plants:

Dicotyledonous weeds of the genera : 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.

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

Le A 18 690

21084 8.

Monocotyledonous weeds of the genera : Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monocharia, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ishaemum , Spenoclea, Daztyloctenium, Agrostis, Alopecurus, Apera.

Monocotyledonous 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.

The compounds are useful depending on the concentration for total weed inoculation e.g. on industrial and railway tracks and on paths and squares with and without tree cover. Similarly, the compounds for weed control in permanent crops, e.g. Forest, ornamental, fruit, wine, citrus, nut, banana, coffee, tea, gum, oil palm, cocoa, berry fruit and hop plants and used for selective weed control in annual crops.

The active compounds according to the invention are distinguished, in addition to the good total herbicidal action, above all by their selective use in important crop plants, such as cotton, beets, rapeseed, cereals, maize and soybeans. They are primarily suitable for pre-emergence applications, but they also have an effect on post-emergence applications. To enhance the effect, combinations with metribuzin, metamitron, methabenzthiazuron, diuron, fluometuron, and the like are useful. possible.

Le A 18 690

2 1 084 8 -44-

The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, aerosols, suspension emulsion concentrates, seed powders, active substance-impregnated natural and synthetic substances and ultrafine encapsulates polymeric substances.

These formulations are prepared in a known manner, e.g. by mixing the active compounds with extenders, that is to say liquid solvents and / or solid carriers, if appropriate under mixing. use of surface-active agents, ie emulsifiers and / or dispersants and / or foam-forming agents. In the case of using water as an extender, e.g. also organic solvents can be used as auxiliary solvents. Suitable liquid solvents are essentially: aromatics, such as xylene, toluene, or alkyl naphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. Petroleum fractions, 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

Le A 18 690

210843

solid carriers: ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates; as solid carriers for granules: crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite, as well as synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; as emulsifying and / or foam-forming gowns: nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, arylsulfonates and protein hydrolysates; as a dispersing agent: e.g. Lignin liquor liquors and methylcellulose.

Adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-type polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, can be used in the formulations.

Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

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

Le A 18 690

210848

The active compounds according to the invention, as such or in their formulations, can also be used for combating weeds in admixture with known herbicides, ready-to-use formulation or tank mixing being possible. Also a mixture with other known active ingredients. Such as fungicides, insecticides, acaricides, nematicides, bird repellants, growth factors, plant nutrients and soil conditioners.

The active compounds can be used 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 and granules. The application is done in the usual way, e.g. by pouring, spraying, spraying, dusting, spreading, dry pickling, moist pickling, wet pickling, slurry pickling or encrusting.

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

The amount of active ingredient used can vary within larger ranges. It depends essentially on the type of effect desired. In general, the Aufvandmengen are between 0.1 and 20 kg of active ingredient per ha, preferably between 0.2 5 and 10 kg / ha.

Le A 18 690

In the following example, the compound given below is used as reference substance:

C ₂ H ₅

^C 2 ^H 5

(2, e-diethyl-N-methyloxy-ethyl-chloroacetanilide)

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Example A

·· # Pre-emergence test

Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether

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

Seeds of the test plants are sown in normal soil and watered after 2 hours with the preparation of active compound. It is advisable to keep the amount of water per unit area expediently constant. The concentration of active ingredient in the preparation does not matter, only the application rate of the active ingredient per unit area is decisive. After three weeks, the degree of damage of the plants is rated in % damage in comparison to the development of the untreated control. It means:

O % = no effect (as untreated control) 100 % = total destruction

The active compounds (1), (3), (4) and (5) according to the invention show in this test a better selective herbicidal activity than the substance (A) known from the prior art.

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- 49 production examples

example 1

CH

16.3 g (0.07 mol) of 2-ethyl-6-methyl-N - [(2-methyl-1,3,4-oxediazol-5-yl) -methyl] -aniline and 6 g (0.076 mol) of anhydrous pyridine are heated to boiling in 100 ml of absolute tetrahydrofuran with stirring and treated dropwise with a solution of 8g (0.07 mol) of chloroacetyl chloride in 20 ml of tetrahydrofuran. After completion of the dropwise addition is allowed to stir for 10 minutes, concentrated by distilling off the solvent and the residue is stirred with 150 ml of water. The crystallizing reaction product is filtered off with suction, washed with water and dried. This gives 18.7 g (.87% of theory) of beige crystals of 2-ethyl-6-methyl-N - [(2-methyl-1,3,4-oxadiazol-5-yl) -methyl]. chloroacetanilide of melting point 67-70 ° C.

A mixture of 101.2 g (0.76 mol) 2-ethyl-6-methyl-aniline, 40 g (0.3 mol) 5-chloromethyl-l, 3,4-oxadiazole _t 41.4 g (0.3 mol) powdered potassium carbonate and 76ml dimethylformamide becomes 5

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Hours with stirring to 10O ⁰ C heated. The reaction mixture is then filtered, the filtrate is diluted with methylene chloride and washed several times with water The methylene chloride phase is dried over sodium sulphate and concentrated in vacuo by distilling off the solvent The residue is distilled under reduced pressure to give 46.8 g (67%) 5 % of theory) yellowish OeI of 2-ethyl-6-methyl-N - [(2-methyl-1,3,4-oxadiazol-5-yl) -methyl] -aniline of boiling point 14O-142 ° C / 0 , 1mm with a purity of 94 (determined by gas chromatography).

Example 2

SCH ₃ CH,

5 g (0.017 mol) of 2,6-diethyl-N - [(1-methyl-2-methylthio-l, 3,4-triazol-5-yl) -methyl] -aniline and 1.6 g (0.02 mol) Pyridine are stirred in 100 ml of absolute tetrahydrofuran and treated dropwise at room temperature with 2.3 g (0.02 mol) of chloroacetyl chloride, the temperature rises to about 30 ⁰ C. The mixture is stirred for 2 hours, partially concentrated by distilling off the solvent and mixed with water. The crystallizing product is filtered off, dried and recrystallized from diisopropyl ether / ethyl acetate. This gives 5 g (80% of Thecrie) of 2,6-diethyl-N - [(1-methyl-2-methylthio-l, 3,4-triazol-5-yl) -methyl] -chloroacetanilide of; Melting point 121-123 ⁰ C.

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first example

13.9 g (0.05 mol) of 2,6-diethyl-N - [(1-methyl-2-thiono-1,3,3-triazol-5-yl) -methyl] -aniline are dissolved in a two-phase mixture at room temperature from 15C ml of toluene and 40 ml of 50% sodium hydroxide solution with the addition of 1.5 g of triethylbenzyl-ammonium chloride (TEBA) as catalyst rapidly stirred and treated dropwise with 6i5g (0.05 mol) of dimethyl sulfate, the temperature to about 35 ⁰ C increases. The mixture is stirred for 5 hours, the toluene phase is separated off, washed several times with water, dried over sodium sulfate and concentrated by distilling off the solvent. The remaining OeI is brought to crystallization by the addition of petroleum ether. After recrystallization from petroleum ether 6.7 g (40 % of theory) of 2,6-diethyl-N - [(lmethyl-2-methylthio-l, 3,4-triazol-5-yl) -methyl] -aniline of the melting point 65-67 ⁰ C.

., - CH ₂ N NH -H N ' Γ ι I CH ₃

C ₂ H ₅

29.6 g (0.1 mol) of 1-methyl-4- [(2,6-diethylanilino) acetyl] -thiosemicarbazide are suspended in 150 ml of ethanol and, after addition of 7 g of potassium hydroxide in 20 ml of water for 1 hour under reflux heated. Afterwards, most of the solvent is distilled off and the residue is mixed with 25 ml of water. After acidification with glacial acetic acid to pH 5

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the resulting precipitate is filtered off and washed thoroughly with water. After drying, 27 g (97 % of theory) of 2,6-diethyl-N- [(l-methyl ^ -thiono-l ^ A yl) -methyl] -aniline of melting point 117-121 ⁰ C.

/ C ₂ H ₉

s CH ₂ -CO-NH-NH-CS-NHCh ₃

C ₂ H ₉

44.2 g (0.2 mol) of 2,6-diethyl-anilino-acetic acid hydrazide and 14.8 g (0.2 mol) of methyl mustard oil are dissolved in 250 ml of ethanol and heated to reflux temperature for one hour. After the subsequent cooling to room temperature, the resulting precipitate is filtered off with suction and washed twice with 50 ml of ethanol. After drying, 46 g (78% of theory) of 1-methyl "4 ^ 2,6-diethylanilino) -acetylZ-thiosemicarbazid in the form of a colorless crystalline substance of melting point 166 C.

^2H 5

d) <(J) -NH-CH ₂ -C-NH-NH ₂

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58.7 g (0.25 mol) of ethyl 2,6-diethylanilinoacetate, 3 rd and 25 g of hydrazine hydrate are allowed to stand in 200 ml of ethanol for 24 hours. It is then concentrated by distilling off the solvent and the residue is extracted with water. After drying, 50.5 g (91 % of theory) of colorless crystals of 2,6-diethyl-anilino-acetic acid hydrazide of melting point 71-73 ⁰ C.

In a similar manner, those compounds are obtained, which are listed in Table 1 formula.

Table:!

R1

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Example no. R R ¹ Y ^X n A Z Br Br Cl Melting point ( ⁰ C) 3 H CH ₃ C ₂ H, 6-C ₂ H, O Cl 79-82 4 H CH ₃ CH ₃ 6-CH ₃ O Cl 91-93 5 H CH ₃ C (CH ₃ > 3 - O Cl 102-04 6 7 H H -S-CHj-CH = CH ₂ -S-CH ₂ -O C ₂ H, CH ₃ 6-C ₂ H ₅ 6-C ₃ H, CH ₃ T CHj O Cl Cl 67-70 ° 115-20 8th H C ₂ H, CH ₃ 6-Cj H ₃ O Cl 57-59 9 H CJH, C ₂ H, 6-Cj H, O Cl 43-47 10 H 1-C ₃ H ₇ CHj 6-C ₂ H, Cl zähfl.Oel 11 H CH ₃ CH ₃ 3-CH ₃ ! V Cl A-CH, glassy solidifies 12 13 14 H H H CH ₃ CH ₃ CH ₃ H-OO I X to Ow χ Ul UI X 6-C ₂ H ₅ 6-C ₂ H _{5 7} 6-iC ₃ H O O 7 ° 80 ° 92-94 ° C 135-37 °

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According to one or more of the processes described in the application, the starting materials formulated in the table below are obtained.

T a b e 1 1 e 2

Example no. R R ¹ Y ^X n A melting point η jzw. refraction index HI H CH ₃ ^C 2 ^H 5 6-C ₂ H _c 0 η ²² = 1.540 ΪΙ-2 H CH ₃ CH ₃ 6-C ₂ HJ 0 ng ² = 1.547 II-3 H CH ₃ CH ₃ 6-CH ₃ 0 η * ² 1,552 II-4 H CH ₃ ~ (CH ₃ ) ₃ - 0 52-55 II-5 H CH ₃ 1-C ₃ H ₇ 6-i ~ C ₃ H. 0 96-99 II-6 H ^C 2 ^H 5 ^C 2 ^H 5 6-C ₂ H ₅ 0 η ²² - 1.534 7-II H C ₂ H ₅ CH ₃ 6-C ₂ H ₅ 0 ij * ¹ - 1,542 II-8 H 1-C ₃ H ₇ CH ₃ 6-C ₂ H ₅ 0 Ip ¹ »1.531 II-9 H SCH ₃ C ₂ K ₅ 6- ^ ₂ H ₅ ^ N-CH ₃ > 5-57 11-10 H S-CH ₂ -QI = ^C 2 »5 6-C ₂ H ₅ ^ N-CH ₃ η ²¹ = 1.577 11-11 H S-CH ₂ - (O) CH ₃ 6-C ₂ H ₅ , N-CH ₃ Tough oil 11-12 H CH ₃ CH ₃ 3-CH ₃ 142-143

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Claims (4)

He faunungsansprttiche 1. A herbicidal composition, characterized in that it contains a content of U'-Azolylalkyl-haloacetanilides of the formula (I) in which  "· Ρ A is oxygen, sulfur or the grouping> NR. stands, R is hydrogen or alkyl, R is hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, halogen, optionally substituted aryl and aralkyl or the groupings -OR,. ~ SR ³ and HR ² R ³ , R is hydrogen, alkyl, or optionally substituted aryl, '... B? is hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl or optionally substituted aralkyl, X is alkyl, Y is alkyl or halogen » Z is halogen and "- ' η for the numbers 0, 1 or 2 stands next to extender · :. ". and / or surface-active agents. 2 ί 084 8 - 57 - Berlin, d ₀ 28.05.1979 APC O7D / 21O 848 54 886 12 Point 1 on the weeds and / or their habitat, 2 »method for combating weeds, characterized in that IT azolylalkyl-haloacetanilides after 3 »Use of N ~ azolylalkyl-haloacetanilides according to item 1, characterized in that they are used for controlling weeds« 4. A process for the preparation of herbicidal compositions, characterized in that mixing N-Azolylalkylhalogenacetanilide according to item 1 with extenders and / or surface-active agents *