Tetrazolinone derivatives

Details Tetrazolinone derivatives Tetrazolinone derivatives

2001-11-15

2003-04-15

McKane, Joseph K. (Department: 1626)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

Reexamination Certificate

active

06548450

ABSTRACT:

This is a 371 of PCT/IB00/00588 filed May 8, 2000.
The present invention relates to novel tetrazolinone derivatives, to processes for their preparation and to their use as herbicides.
In Japanese Laid-Open Patent Publications No. 82258/1995, No. 97372/1995 and No. 118246/1995 there are disclosed preparation processes of some tetrazolinone derivatives and a preparation process of 1-substituted-5(4H)-tetrazolinones, the intermediates thereof. Moreover, the EP-A-146,279 discloses that some tetrazolinone derivatives have herbicidal activities.
However, the known tetrazolinone derivatives are not fully satisfactory with regard to their herbicidal activity and their phytotoxicity against crops.
According to the invention there have now been found novel tetrazolinone derivatives of the general formula (I)
wherein
R
1
represents methyl or ethyl,
R
2
represents halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, phenyl, phenoxy, alkoxycarbonyl, nitro or cyano, and n represents 0, 1, 2, 3, 4 or 5.
The compounds of the formula (I), according to the invention, can be obtained by a process in which
a) compounds of the general formula (II)
 wherein
R
1
is defined as mentioned above, are reacted with compounds of the general formula (III)
 wherein
R
2
and n are defined as mentioned above, and
M represents a leaving group such as chloro or bromo
in the presence of an inert solvent and, if appropriate, in the presence of a base.
The compounds of the formula (I) of the present invention posses strong herbicidal activities and especially demonstrate an excellent herbicidal effect compared with the known compounds described in the aforementioned EP-A-146,279 which are similar to the compounds of the formula (I). The compounds of the invention nevertheless also show a good compatibility with crops. Therefore, the compounds of the present invention can be potentially employed as agrochemicals, specifically as herbicides.
In the formulae mentioned above:
Halogen in “halogen”, “haloalkyl”, “haloalkoxy” and “haloalkylthio” represents fluoro, chloro, bromo or iodo, and preferably fluoro, chloro or bromo.
“Alkyl” may be straight chain or branched chain and there may be mentioned, for example, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, n- or iso-pentyl, tert-amyl, pentan-3-yl, neopentyl and n-hexyl.
“Alkoxy” may be straight chain or branched chain and there may be mentioned, for example, methoxy, ethoxy, propoxy, isopropoxy, n-, iso-, sec- or tert-butoxy, n-pentyloxy and n-hexyloxy.
“Alkylthio” may be straight chain or branched chain and there may be mentioned, for example, methylthio, ethylthio, n-propylthio, isopropylthio and n-butylthio.
“Alkylsulfinyl” may be straight chain or branched chain and there may be mentioned, for example, methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl and n-butylsulfinyl.
“Alkylsulfonyl” may be straight chain or branched chain and there may be mentioned, for example, methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropyl-sulfonyl and n-butylsulfonyl.
“Haloalkyl” may be straight chain or branched chain and there may be mentioned, for example, difluoromethyl, trifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl, 1,1,2,2,2-pentafluoroethyl, 2,2,3,3,3-pentafluoropropyl, 3-chloropropyl, 1,3-difluoropropan-2-yl, 1,1,1-trifluoropropan-2-yl, 2,2,3,3,4,4,4-heptafluorobutyl and 3-bromopropyl.
The Haloalkyl part of “haloalkoxy” and “haloalkylthio” may be as defined in the above-mentioned “haloalkyl”.
As “alkoxycarbonyl” there may be mentioned, for example, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl and n-butoxycarbonyl.
As a preferable group of compounds of the present invention there can be mentioned the compounds of the aforementioned formula (I) wherein
R
1
represents methyl or ethyl,
R
2
represents fluoro, chloro, bromo, C
1-4
alkyl, C
1-4
haloalkyl, C
1-4
alkoxy, C
1-4
haloalkoxy, C
1-4
alkylthio, C
1-4
haloalkylthio, C
1-4
alkylsulfinyl, C
1-4
alkylsulfonyl, phenyl, phenoxy, C
1-4
alkoxycarbonyl, nitro or cyano, and n represents 0, 1, 2, 3 or 4.
As a more preferable group of compounds of the present invention there can be mentioned the compounds of the aforementioned formula (I) wherein
R
1
represents methyl,
R
2
represents fluoro, chloro, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trifluoromethyl, methoxy, ethoxy, isopropoxy, trifluoromethoxy, difluoromethoxy, 2,2,2-trifluoroethoxy, methylthio, ethylthio, isopropylthio, methysulfinyl, methylsulfonyl, phenyl, phenoxy, methoxycarbonyl, ethoxycarbonyl, nitro or cyano, and n represents 0, 1, 2, or 3.
Among the compounds of the aforementioned formula (I) there may be especially pointed out the compounds which are represented by the following formula
wherein the carbon atom marked with * represents an asymmetric carbon atom and R
1
and R
2
have the same meaning as mentioned above. Based on this fact the compounds of the present invention can exist as pure optically active enantiomers or in a form of optional mixtures of optically active enantiomers. Therefore, the compounds of the aforementioned formula (I) of the present invention include optically active substances and mixtures thereof.
Using, for example, 1-((S)-&agr;-methylbenzyl)-5(4H)-tetrazolinone and N-isopropyl-N-phenylcarbamoyl chloride as the starting materials according to preparation process a), the said preparation process can be illustrated by the following reaction scheme:
The compounds of the formula (II), which are used as the starting materials in the aforementioned preparation process a) are novel compounds, which were not described in literature, and can be prepared, for example, by the following proccesses in which
according to process variant b) compounds of the general formula (IV)
 wherein
R
1
is defined as mentioned above,
are reacted with trimethylsilyl azide in the presence of a catalytic amount of boron trifluoride-ether-complex, or
according to process variant c) compounds of the above-mentioned general formula (IV) are reacted with sodium azide in a polar solvent in the presence of a catalytic quantity of aluminium chloride.
The compounds of the general formula (IV) which are used as the starting material in the above-mentioned preparation process variants b) and c) include isocyanates known in the area of organic chemistry and can be easily obtained, for example, by reacting amines of the general formula (V)
wherein
R
1
is as defined above,
with, for example, phosgene according to known methods described, for example, in “SHIN JIKKEN KAGAKU KOUZA” (New experimental chemistry lecture) Vol. 14, III, pp.1490-1496 (published by Maruzen Ltd. on Feb. 20, 1978).
The compounds of the above-mentioned formula (V) can be synthesized, for example, similarly to the methods described in “SHIN JIKKEN KAGAKU KOUZA” (New experimental chemistry lecture) Vol. 14, III, pp.1332-1398 (published by Maruzen Ltd. on Feb. 20, 1978) or Organic Reactions, Vol. 5, 1949, 301-330 (John Wiley & Sons, Inc.).
As compounds of the above-mentioned formula (II) there can be mentioned the following species:
1-((S)-&agr;-methylbenzyl)-5(4H)-tetrazolinone,
1-((R)-&agr;-methylbenzyl)-5(4H)-tetrazolinone,
1-((S)-&agr;-ethylbenzyl)-5(4H)-tetrazolinone,
1-((R)-&agr;-ethylbenzyl)-5(4H)-tetrazolinone.
The compounds of the formula (III) to be reacted with the compounds of the above-mentioned formula (II) include N-isopropyl-N-(substituted)phenylcarbamoyl halides which are well known in the area of organic chemistry. As typical examples of them there can be mentioned the following compounds:
N-isopropyl-N-phenylcarbamoyl chloride,
N-isopropyl-N-(4-fluorophenyl)carbamoyl chloride,
N-isopropyl-N-(3-methylphenyl)carbamoyl chloride,
N-isopropyl-N-(4-trifluoromethylphenyl)carbamoyl chloride,
N-isopropyl-N-(2-ethoxyphenyl)carbamoyl chloride,
N-isopropyl-N-(4-difluoromethoxyphenyl)carbamoyl chloride,
N-isopropyl-N-(4-isopropylthiophenyl)carbamoyl chloride,
N-isopropyl-N-(4-methylsulfi

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