Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1998-08-14
2000-12-12
Shah, Mukund J.
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
544182, 5482622, A01N 43707, C07D253075
Patent
active
061599034
DESCRIPTION:
BRIEF SUMMARY
The invention relates to novel substituted 2-aryl-1,2,4-triazine-3,5-di(thi)ones, to processes for their preparation and to their use as herbicides.
EP 11693, EP 271170, WO 86/00072, U.S. Pat. No. 4,755,217, U.S. Pat. No. 4,878,941, U.S. Pat. No. 4,956,004, U.S. Pat. No. 5,262,390, and U.S. Pat. No. 5,344,812 disclose that certain substituted 2-aryl-1,2,4-triazine-(thi)ones have herbicidal properties. However, the compounds described therein have not attained any major importance.
This invention, accordingly, provides the novel substituted 2-aryl-1,2,4-triazine-3,5-di(thi)ones of the general formula (I), ##STR2## in which Q.sup.1 represents oxygen or sulphur, optionally substitutued alkyl, alkoxy, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkenyl, alkenylcarbonyl, alkenyloxycarbonyl, alkinyl, alkinylcarbonyl, alkinyloxycarbonyl, cycloalkyl or cycloalkylalkyl, thiocarbamoyl, amino, or represents respectively optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino, alkenyl, alkenyloxy, alkenylthio, alkinyl, alkinyloxy, alkinylthio, cycloalkyl or cycloalkylalkyl, --SO.sub.2 --, --CO-- or the grouping --N--A.sup.4 --, where A.sup.4 represents hydrogen, hydroxyl, alkyl, alkenyl, alkinyl, alkoxy, aryl, alkylcarbonyl, arylcarbonyl, alkylsulphonyl or arylsulphonyl, alkanediyl, alkenediyl, azaalkenediyl, alkinediyl, cycloalkanediyl, cycloalkenediyl or phenylene, --SO.sub.2 --, --CO-- or the grouping --N--A.sup.4 --, where A.sup.4 represents hydrogen, hydroxyl, alkyl, alkoxy, aryl, alkylsulphonyl or arylsulphonyl, alkanediyl, alkenediyl, azaalkenediyl, alkinediyl, cycloalkanediyl, cycloalkenediyl or phenylene, and/or A.sup.2 do not represent a single bond thiocyanato, nitro, carboxyl, carbamoyl, thiocarbamoyl, sulpho, chlorosulphonyl, halogen, represents respectively optionally halogen- or alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkoxycarbonyl or dialkoxy(thio)phosphoryl, represents respectively optionally halogen-substituted alkenyl, alkenyloxy, alkenylthio, alkenylamino, alkylideneamino, alkenyloxycarbonyl, alkinyl, alkinyloxy, alkinylthio, alkinylamino or alkinyloxycarbonyl, represents respectively optionally halogen-, cyano-, carboxyl-, alkyl- and/or alkoxy-carbonyl-substituted cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylideneamino, cycloalkyloxy-carbonyl or cycloalkylalkoxy-carbonyl, or represents respectively optionally nitro-, cyano-carboxyl-, halogen-, alkyl-, halogenalkyl-, alkyloxy-, halogenalkyloxy- and/or alkoxy-carbonyl-substituted aryl, aryloxy, aralkyl, arylalkoxy, aryloxycarbonyl or arylalkoxycarbonyl, hydrogenated pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, oxiranyl, oxetanyl, dioxolanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolylalkyl, furylalkyl, thienylalkyl, oxazolylalkyl, isoxazolylalkyl, thiazolylalkyl, pyridinylalkyl, pyrimidinylalkyl, pyrazolylalkoxy, furylalkoxy, represents perhydropyranylalkoxy or pyridylalkoxy.
The novel substituted 2-aryl-1,2,4-triazine-3,5-di(thi)ones of the general formula (I), are obtained when ##STR3## in which Q.sup.1, Q.sup.2, R.sup.1 and R.sup.2 are each as defined above, ##STR4## in which R.sup.3, R.sup.4 and R.sup.5 are each as defined above and presence of a reaction auxiliary, ##STR5## in which Q.sup.1, Q.sup.2, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are each as defined above are reacted with alkylating agents of the general formula (IV), presence of a reaction auxiliary, ##STR6## in which R.sup.3, R.sup.4 and R.sup.5 are each as defined above presence of a reaction auxiliary and the resulting 2-aryl-1,2,4-triazolidine-3-(thi)ones of the general formula (VII), ##STR7## in which Q.sup.1, R.sup.3, R.sup.4 and R.sup.5 are each as defined above ##STR8## in which R.sup.2 is as defined above presence of a reaction auxiliary, ##STR9## in which R.sup.3, R.sup.4 and R.sup.5 are each as defined above ester of the general formula (X), ##STR10## in which R.sup.
REFERENCES:
patent: 4956004 (1990-09-01), Thiodoridis
Dollinger Markus
Findeisen Kurt
Linker Karl-Heinz
Santel Hans-Joachim
Balasubramanian Venkataraman
Bayer Aktiengesellschaft
Shah Mukund J.
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