IL33903A - Compositions containing(2,1,3-benzothiadiazolyloxy)acetic acid derivatives for regulating plant growth,certain new such compounds and their preparation - Google Patents

Abstract

1303711 Benzothiadiazoles PHILIPS GLOEILAMPENFABRIEKEN NV 16 Feb 1970 [19 Feb 1969] 7314/70 Heading C2C [Also in Divisions A5 and Cl] Compounds of formula wherein X is the group -OCHR 1 COOR, in which R 1 is hydrogen or C 1-3 alkyl and R is hydrogen or C 1-10 alkyl, Y is chlorine or bromine, n is 0, 1, 2 or 3 and Z is hydrogen or C 1-3 -alkyl, are prepared by (a) etherification, (b) halogenation or (c) ester hydrolysis. The products have herbicidal, pesticidal and plant growth regulant activity (see Division A5). 6 - Hydroxy - benzothiadiazole starting materials are prepared by hydrolysis of their methyl ethers. 6 - Methoxy - benzothiadiazoles are prepared by (a) replacement of a chlorine atom by reaction with sodium methoxide, (b) chlorination or (c) reduction of an o-dinitro-benzene or an onitro-aniline to the corresponding diamine, followed by cyclization with thionyl chloride. 2 - Chloro - 4 - methoxy - 6 - nitro - aniline is prepared by reaction of 2-chloro-6-nitro-phenyl azide with sulphuric acid to give 2-chloro-4- hydroxy - 6 - nitro - aniline, followed by methylation. 2,3,5 - Trichloro - 6 - nitro - aniline is prepared by nitration of 2,3,5-trichloro-acetanilide. 2,4 - Dichloro - 5,6 - dinitro - anisole is prepared by nitration of 2,4-dichloro-anisole. [GB1303711A]

Claims (1)

1. CLAIMS Compounds of general formula which formula X the group where is a hydrogen atom or an alfcyl group containing from 1 to 3 carbon atoms and R represents a hydrogen atom or an group containing f om 1 to 10 carbon chlorine or bromine a lower alkyl and n 2 or 0 or with the proviso that if n 3 then m and with the understanding that R cannot represent a hydrogen atom when n 0 and H and R cannot represent a hydrogen atom or an alkyl group of less tha 3 carbon if the substituent X is at th of the ring the substituent Y occupies both the and position the substituent is a hydrogen Compounds of the general formula where X is a group occupying the or position of the ring in which group R represents a hydrogen atom or an alfcyl group containing from 1 to carbon 2 with the understanding that R represents an alkyl group containing from 3 to 10 carbon atoms if n or if the substituent X occupies the of the ring structure and the substituent Y occupies both the and the Compounds of the general where R is a hydrogen or an ethyl grou and n 2 or 3 represents which is at the positions 5 and 6 of the ring whe n with the proviso that whe n the R cannot be Compounds of the general formula wherein R is a hydrogen atom or an ethyl and n 2 or 3 Y represents chlorine which is at the positions 4 and 6 or 4 and 7 of the ring structure when n with the proviso that when n then R cannot be Compounds of the formula where R is an alkyl group containing from 3 10 carbon atoms A compound of the formula A compound of the formula A compound of the formula A compound of the formula A compound of the formula A compound of the formula A compound of the formula A compound of the formula A compound of the formula compound of the formula A compound of the formula compound of A compound of the formula A preparation for influencing plant characterized that preparation contains a compound of 3739 in which formula gen atom or an alkyl group carbon and R represents a hydrogen atom or an alkyl group containing from 1 10 carbon Y a chlorine or bromine Z a lower alkyl n 0 2 or 3 and m 0 or with the proviso tha if n 3 then m as the active constituent combined with a solid or liquid inert carrier preparation as claimed in Claim characterized in that the preparation contains a compound of the where X is a group which occupies the tion of and in which R represents a hydrogen atom or an alkyl group containing from 1 to 10 carbon Y is a chlorine and n 2 or 3 as the active in that it E as l 3 t is is β 5 in that as the active it a of is is is at and 6 4 of 373 A preparation as claimed in Claim characterized that it contains as the active constituent a compou the formula where is a hydrogen atom or an alkyl group containing from 1 to 10 carbon 24 A preparation as claimed in Claim 1 characterized in that it contains a compound of the formula as the active 25 preparation as claimed in Claim 19 characterized in that it contains a compound of the formula as the active A as claimed in Claim characterized 3739 as the active 2 A preparation as claimed in Claim characterized in that it contains a compound of the formula as the active characterized in that it contains a compound of the formula the active A preparation as claimed in Claim charact that it contains a compound of the formula as the active A preparation as claimed in Claim characterized in that it contains a compound of the formula as the active A preparation as claimed in Claiin characterized in that it contains a of as the active constituent preparation as claimed in Claim characterized in that it contains a the formula as active constituent A preparation as claimed in Claim characterised in that it contains a of the formula PHN 3739 as the active A preparation as claimed in Claim characterized that it contains a compound of the formula as the active A preparation as claimed in Claim characterized that it contains a compound of the formula the active constituent A preparation as claimed in Claim characterized in that it contains a compound of the formula as the active preparation as cllaaiimmeedd iinn CCllaaiimm characterized in that it contains a compound of the formula r PH 3739 as the active A preparation as claimed in Claim characterized in that it contains a compound of the as the active 9i A preparation as claimed in any of Claims characterized in that it also contains a second herbicidal A method for producing a preparation as claimed in any of Claims to characterized in that a compound of the formula in which formula tho group 0CKC00R re a hydrogen atom or an alkyl group containing from 1 ro 3 carbon atoms and R represents a hydr atom or an alkyl containing from 1 to 10 carbon a chlorine or bromine 1 is mixed with a solid or liquid carrier A method of producing compounds of the general formula in which where is a hydrogen atom or an group containing from 1 to 3 carbon atoms and R represents a hydrogen atom or an group containing from 1 to 10 carbon Y a chlorine or bromine Z lower alkyl 2 or and 0 or with the proviso that if 3 then with the understanding that R cannot represent a hydrogen atom whe n 0 and H and R cannot a hydrogen atom or an alkyl group of less than 3 carbon if the substituent X is at the of the ring the substituent Y occupies both the and position and the substituent is a hydrogen characterized in that the compounds are prepared in a manner known for similar substances or in an analogous A method as claimed in Claim characterized in that a compound of the formula where A is a hydroxy is a chlorine or bromine Z is a lower alkyl n 2 o and 0 or with the proviso that if n 3 then is reacted with a compound of the formula Hal COOR in formula represents a hydrogen atom or an alkyl group containing from 1 to 3 carbon R represents an alkyl group containing from 1 10 carbon and represents a in the of ah acid A method as claimed Claim characterized a compound of the formula which formula X represents where is a hydrogen atom or an group containing from 1 to 3 carbon atoms and R is a groupjcontaining from 1 to 10 carbon Z is a lowe alkyl and a 0 or is treated with a chlorinating or brominating A method as claimed in Claim characterized in that in which X is the group where represents a hydrogen atom or an alkyl group containing from 1 to 3 carbon atoms and presents an alkyl group containing from 1 to 10 carbon Y a chlorine or bromine 2 represents or a lower n 2 or and m 0 or with the proviso that if n 3 then is subjected to a hydrolysis in which the group of the converted into a carboxylic acid A method of regulating plant characterized by the use of a preparation as claimed in an of Claims 19 to insufficientOCRQuality