Herbicidal...

Details Herbicidal... Herbicidal...

2002-01-24

2003-08-05

McKane, Joseph K. (Department: 1626)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C548S136000

Reexamination Certificate

active

06602827

ABSTRACT:

FIELD OF THE INVENTION
The invention relates to novel 5-chlorodifluoromethyl-1,3,4-thiadiazol-2-yl-oxyacetanilides, to a process for their preparation and to their use as herbicides.
BACKGROUND OF THE INVENTION
It is already known that certain 5-chlorodifluoromethyl-1,3,4-thiadiazol-2-yl-oxyacetanilides such as, for example, the compounds N-methyl-5-chlorodifluoromethyl-1,3,4-thiadiazol-2-yl-oxyacetanilide, N-ethyl-5-chlorodifluoromethyl-1,3,4-thiadiazol-2-yl-oxyacetanilide, 4-chloro-N-methyl-(5-chlorodifluoromethyl-1,3,4-thiadiazol-2-yl)-oxyacetanilide and 3-trifluoromethyl-N-methyl-(5-chlorodifluoromethyl-1,3,4-thiadiazol-2-yl)-oxyacetanilide (cf.EP-A-148501/ U.S. Pat. No. 4,798,731), the compound N-i-propyl-5-chlorodifluoromethyl-1,3,4-thiadiazol-2-yl-oxyacetanilide (cf. EP-A-348737/U.S. Pat. No. 4,968,342) and the compounds 4-fluoro-N-methyl-(5-chlorodifluoromethyl-1,3,4-thiadiazol-2-yl)-oxyacetanilide and 4-fluoro-N-ethyl-(5-chlorodifluoromethyl-1,3,4-thiadiazol-2-yl)-oxyacetanilide have herbicidal properties (cf. EP-A-626380). However, the activity of these prior-art compounds is, in particular at low application rates and concentrations, not entirely satisfactory in all areas of use.
SUMMARY OF THE INVENTION
The present invention provides a 5-chlorodifluoromethyl-1,3,4-thiadiazol-2-yl-oxyacetanilide of the general formula (I)
wherein
n represents the number 0, 1, 2 or 3,
R represents straight-chain or branched alkyl having 1 to 4 carbon atoms, and
X represents nitro, cyano, halogen or represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 4 carbon atoms,
except for the compounds N-methyl-5-chlorodifluoromethyl-1,3,4-thiadiazol-2-yl-oxyacetanilide, N-ethyl-5-chlorodifluoromethyl-1,3,4-thiadiazol-2-yl-oxyacetanilide, 4-chloro-N-methyl-(5-chlorodifluoromethyl-1,3,4-thiadiazol-2-yl)-oxyacetanilide and 3-trifluoromethyl-N-methyl-(5-chlorodifluoromethyl-1,3,4-thiadiazol-2-yl)-oxyacetanilide, N-i-propyl-5-chlorodifluoromethyl-1,3,4-thiadiazol-2-yl-oxyacetanilide, and 4-fluoro-N-methyl-(5-chlorodifluoromethyl-1,3,4-thiadiazol-2-yl)-oxyacetanilide and 4-fluoro-N-ethyl-(5-chlorodifluoromethyl-1,3,4-thiadiazol-2-yl)-oxyacetanilide,
The present invention also provides a process for preparation of the compound. The compound has herbicidal activity.
This invention, accordingly, provides novel 5-chlorodifluoromethyl-1,3,4-thiadiazol-2-yl-oxyacetanilides of the general formula (I)
in which
n represents the number 0, 1, 2 or 3,
R represents straight-chain or branched alkyl having 1 to 4 carbon atoms, and
X represents nitro, cyano, halogen or represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 4 carbon atoms,
except for the compounds N-methyl-5-chlorodifluoromethyl-1,3,4-thiadiazol-2-yl-oxyacetanilide, N-ethyl-5-chlorodifluoromethyl-1,3,4-thiadiazol-2-yl-oxyacetanilide, 4-chloro-N-methyl-(5-chlorodifluoromethyl-1,3,4-thiadiazol-2-yl)-oxyacetanilide and 3-trifluoromethyl-N-methyl-(5-chlorodifluoromethyl-1,3,4-thiadiazol-2-yl)-oxyacetanilide (cf. EP-A-149501/U.S. Pat. No. 4,798,731), N-i-propyl-5-chlorodifluoromethyl-1,3,4-thiadiazol-2-yl-oxyacetanilide (cf. EP-A-348737/U.S. Pat. No. 4,968,342), and 4-fluoro-N-methyl-(5-chlorodifluoromethyl-1,3,4-thiadiazol-2-yl)-oxyacetanilide and 4-fluoro-N-ethyl-(5-chlorodifluoromethyl-1,3,4-thiadiazol-2-yl)-oxyacetanilide (cf. EP-A-626380)-.
Preferred substituents or ranges of the radicals present in the formulae listed above and below are described below.
n preferably represents the number 0, 1 or 2.
R preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.
X preferably represents nitro, cyano, fluorine, chlorine, bromine or represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, methylthio, ethylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl.
n particularly preferably represents the number 0, 1 or 2.
R particularly preferably represents methyl, ethyl, n- or i-propyl, s- or t-butyl.
X particularly preferably represents nitro, cyano, fluorine, chlorine, bromine or represents in each case optionally fluorine- or chlorine-substituted methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl.
n very particularly preferably represents the number 0, 1 or 2.
R very particularly preferably represents methyl, ethyl, n- or i-propyl, s- or t-butyl.
X very particularly preferably represents cyano, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy or trifluoromethoxy.
The general or preferred radical definitions listed 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 if desired, i.e. including combinations between the given preferred ranges.
Preference according to the invention is given to those compounds of the formula (I) which contain a combination of the meanings listed above as being preferred.
Particular preference according to the invention is given to those compounds of the formula (I) which contain a combination of the meanings listed above as being particularly preferred.
Very particular preference according to the invention is given to those compounds of the formula (I) which contain a combination of the meanings listed above as being very particularly preferred.
Optionally substituted radicals can be mono- or polysubstituted, where, in the case of polysubstitution, the substituents can be identical or different.
Examples of the compounds of the general formula (I) according to the invention are listed in the groups below.
Group 1
Examples of the meanings of X
n
and (as a prefix in brackets) the positions of X
n
are given below:
n=0 (i.e. X═H);
n=1 (i.e. X different from H); in this case, X represents, for example, (2) CN, (3) CN, (4) CN, (2) F, (3) F, (4) F, (2) Cl, (3) Cl, (4) Cl, (2) CH
3
, (3) CH
3
, (4) CH
3
, (2) C
2
H
5
, (3) C
2
H
5
, (4) C
2
H
5
, (2) CF
3
, (3) CF
3
, (4) CF
3
, (2) Br, (3), Br, (4) Br, (2) OCH
3
, (3) OCH
3
, (4) OCH
3
, (2) OCF
3
, (3) OCF
3
, (4) OCF
3
;
n=2 (i.e. X different from H); X is then located in two positions (with identical or different meaning) and represents, for example, (2,3) F
2
, (2,4) F
2
, (2,5) F
2
, (3,4) F
2
, (3,5) F
2
, (2) F/(3) Cl, (2) F/(4) Cl, (2) F/(5) Cl, (3) F/(4) Cl, (2) F/(3) Br, (2) F/ (4) Br, (2) F/(5) Br, (2) F/(3) CH
3
, (2) F/(4) CH
3
, (2) F/(5) CH
3
, (3) F/(4) CH
3
, (2) F/(3) C
2
H
5
, (2) F/(4) C
2
H
5
, (2) F/(5) C
2
H
5
, (2) F/(3) CF
3
, (2) F/(4) CF
3
, (2) F/(5) CF
3
, (2,3) Cl
2
, (2,4) Cl
2
, (2,5) Cl
2
, (3,4) Cl
2
, (2) Cl/(3) F, (2) Cl/(4) F, (2) Cl/(5) F, (3) Cl/(4) F, (2) Cl/(3) Br, (2) Cl/(4) Br, (2) Cl/(5) Br, (2) Cl/(3) CH
3
, (2) Cl/(4) CH
3
, (2) Cl/(5) CH
3
, (2) Cl/(3) C
2
H
5
, (2) Cl/(4) C
2
H
5
, (2) Cl/(5) C
2
H
5
, (2) Cl/(3) CF
3
, (2) Cl/(4) CF
3
, (2) Cl/(5) CF
3
, (3) Cl/(4) CF
3
, (2) Br/(3) F, (2) Br/(4) F, (2) Br/(5) F, (2) Br/(3) Cl, (2) Br/(4) Cl, (2Br/(5) Cl, (2), (2) Br/(3) CH
3
, (2) Br/(4) CH
3
, (2) Br/(5) CH
3
, (2) Br/(3) CF
3
, (2) Br/(4) CF
3
, (2) Br/(5) CF
3
, (2,3) (CH
3
)
2
, (2,4) (CH
3
)
2
, (2,5) (CH
3
)
2
, (3,4) (CH
3
)
2
, (2) CH
3
/(3) F, (2) CH
3
/(4) F, (2) CH
3
/(5) F, (3) CH
3
/(4) F, (2) CH
3
/(3) Cl, (2CH
3
/(4) Cl, (2) CH
3
/(5) Cl, (2) CH
3
/(3) Br, (2) CH
3
/(4) Br, (2) CH
3
/(5) Br, (2) CH
3
/(3) CF
3
, (2) CH
3
/(4) CF
3
, (2) CH
3
/(5) CF
3
, (2) C
2
H
5
/(3) F, (2) C
2
H
5
/(4) F, (2) C
2
H
5
/(5) F, (2,3) (CF
3
)
2
, (2,4) (CF
3
)
2
, (2,5) (CF
3
)
2
, (2) CF
3
/(3) F, (2) CF
3
/(4) F, (2) CF
3
/(5) F, (2) CF
3
/(3) Cl, (2) CF
3
/(4) Cl, (2) CF
3
/(5) Cl, (2) Cl/(4) OCH
3
, (2) Cl/(5) OCH
3
, (2) F/(4) OCH
3
, (2) OCF
3
/(4) F, (2) OCF
3
/(4) Cl, (2) F/(4) OCF
3
, (2) Cl/(4) O

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