DK172884A

DK172884A - Aniline

Info

Publication number: DK172884A
Application number: DK172884A
Authority: DK
Inventors: Shy-Fuh Lee
Original assignee: Sandoz Ag
Priority date: 1983-03-31
Filing date: 1984-03-29
Publication date: 1984-10-01
Also published as: GB2137990A; AU2622884A; DK172884D0; ES8606245A1; CH659465A5; FR2543549A1; GB8407910D0; IL71390A0; HUT33995A; FR2543549B1; ES531104A0; GB2137990B; CA1198114A; DE3410317A1; TR21962A; NL8400852A

Description

loalkyl, phenyl-Cj_g-alkyl, eller er valgt blandt betydningerne af R' uafhængigt heraf; R' er hydrogen eller en gruppe A, der er cyano-C^_g- alkyl eller -(CHR^-COOR2, -(CHR3)n-CO-R4/ -(CHR3) -SO-j-R4, -(CHR5) ,-O-CO-R6, -(CHR9) ,- η ί η n CO-O-CR^R^-CO-OR12, -(CH,,) .-W-(CH,) ,.-W'-R13 λ n L n eller -CO-CHR14-OR15; R" er nitro, amino, cyano eller chlor; R^ er hydrogen, C^_g-alkyl, C^_Q-alkoxy eller C^_g-al- kylthio; 2 12 hver af R og R er hydrogen, en metal kation, C^_g-alkyl,loalkyl, phenylC1-6 alkyl, or is selected from the meanings of R 'independently; R 'is hydrogen or a group A which is cyano-C1-6 alkyl or - (CHR3 -COOR2, - (CHR3) n-CO-R4 / - (CHR3) -SO-j-R4, - (CHR5 ), -O-CO-R6, - (CHR9), - η ί η n CO-O-CR ^ R ^ -CO-OR12, - (CH ,,).-W- (CH,), .- W "-R13 λ n L n or -CO-CHR14-OR15; R" is nitro, amino, cyano or chloro; R 1 is hydrogen, C 1-6 alkyl, C 1-6 alkoxy or C 1-6 alkylthio 12 each of R and R is hydrogen, a metal cation, C 1-6 alkyl,

Cj.g-alkenyl, Cj.g-alkynyl, Cj.^g-ialkylthioalkyl), Cj.io’ia^oxyalkyl), C^ g-hydroxyalkyl, C2_10-(al-kylsulfinylalkyl), ^.-jQ-Calkylsulfonylalkyl), substitueret eller usubstitueret phenyl, C2_g-cycloalkyl, C^g-halogenalkyl, Cg g-Calkoxyalkoxyalkyl), C^_g-alkylamino, di(C^_g-alkyl)amino, C^.g-eycloalkyl-^1-3*a^yl* en m®ffet 3-8-leddet heterocyclisk gruppe med 1 eller 2 heteroatomer valgt blandt O og N, g N=C(R )2 eller substitueret eller usubstitueret benzyl;Cj.g al alkenyl, Cj.g alk alkynyl, Cj g galkylthioalkyl), Cjio'iaalkoxyalkyl), C ^ hydro2 hydroxyalkyl, C₂_- al (alkylsulfinylalkyl), , substituted or unsubstituted phenyl, C2-6 cycloalkyl, C1-6 haloalkyl, C8-6alkoxyalkoxyalkyl), C1-6 alkylamino, di (C1-6 alkyl) amino, C1-6 cycloalkyl a ^ yl * a saturated 3-8 membered heterocyclic group having 1 or 2 heteroatoms selected from O and N, g N = C (R) 2 or substituted or unsubstituted benzyl;

Λ t AA t A

hver af R"* og R ^ er hydrogen eller Cj g-alkyl; 4 R er C1-8~a*kY*' C2_g-alkenyl, C^ g-alkylthio, C^.g_alkylamino, di(C^_g-alkyl)amino, Cg g-cycloalkyl, C^g-halogenalkyl, substitueret eller usubstitueret phenyl, substitueret eller usubstitueret benzyl, substitueret eller usubstitueret anilino, eller gruppen R5 O I // ic -CH-C-OR , hver af R5 og R16 er hydrogen eller C^g-alkyl; g ^ er C1-8-alkV>* C2_g-(alkoxyalkyl), Cgg-cycloalkyl, C^_g~halogenalkyl, eller substitueret eller usubstitueret phenyl; eller sammen med R5 danner en C- .-al- 2-4 kylen- eller en C2_^-alkenylengruppe; hver af R® og R^ er Cjg-alkyl; hver af R®, R1® og R11 uafhængigt af hinanden er valgt blandt hydrogen, C^g-alkyl, C^g-alkoxy og Cl g-alkylthio; er substitueret eller usubstitueret phenyl, eller usubstitueret eller substitueret phenoxyphenyl; n er 0, 1 eller 2, n‘ og n" uafhængigt af hinanden er 1 eller 2; og hver af W og W’ uafhængigt af hinanden er oxygen eller svovl, der fremstilles ved, ateach of R4 and R4 is hydrogen or C1-6 alkyl; 4R is C1-8 ~ a * kY * 'C2-6 alkenyl, C1-6 alkylthio, C1-6 alkylamino, di (C1-6 alkyl) ) amino, C 1-6 cycloalkyl, C 1-6 haloalkyl, substituted or unsubstituted phenyl, substituted or unsubstituted benzyl, substituted or unsubstituted anilino, or the group R 5 O or C1-6 alkyl; g1 is C1-8 alkV> * C2-6 (alkoxyalkyl), C8- cycloalkyl, C1-6 haloalkyl, or substituted or unsubstituted phenyl; or together with R5 forms a C - 2-4 kylene or a C2-6 alkenylene group; each of R® and R4 is C1-6 alkyl; each of R®, R1® and R11 is independently selected from hydrogen, C1-6 alkyl, C1 g-alkoxy and C1-6 alkylthio; is substituted or unsubstituted phenyl, or unsubstituted or substituted phenoxyphenyl; n is 0, 1 or 2, n 'and n "are independently 1 or 2; and each of W and W 'is independently oxygen or sulfur produced by the fact that

a) den aktiverede NOj-gruppe i 2-stillingen på en 4-substitueret 1,2-dinitrobenzenforbindelse med den almene formel IIa) the activated NO 2 group at the 2-position of a 4-substituted 1,2-dinitrobenzene compound of the general formula II

II.II.

hvor X, Y, Z, M og t er som ovenfor defineret, erstattes med en alkoxyaminogruppe med den almene formel IIIwherein X, Y, Z, M and t are as defined above are replaced by an alkoxyamino group of general formula III

IIIIII

hvor R er som ovenfor defineret, efterfulgt, hvis det ønskes, og i passende rækkefølge, af N-substitution af den således introducerede alkoxyaminogruppe med en gruppe A, der er som defineret for R’ med undtagelse af H, og/eller hydrogenering af NC^-gruppen, der sidder i ortho-stilling i forhold til den introducerede alkoxyaminogruppe til en Nh^-gruppe, og/eller erstatning af den sidstnævnte NHj-gruppe med Cl eller en CN-gruppe og/-eller hydrolysering af en hvilken som helst carboxylsyreestergruppe til den fri carboxylsyre eller dens saltform; b) eller der opnås en forbindelse med den almene formel lawherein R is as defined above, followed, if desired, and in appropriate order, by N-substitution of the alkoxyamino group thus introduced with a group A as defined for R 'with the exception of H, and / or hydrogenation of NC the ^ group sitting in ortho position relative to the introduced alkoxyamino group to an Nh ^ group, and / or replacing the latter NH 2 group with Cl or a CN group and / or hydrolyzing any carboxylic acid ester group for the free carboxylic acid or its salt form; b) or a compound of the general formula Ia is obtained

la hvor X, Y, Ζ, Μ, t, R og R’ er som ovenfor defineret, ved N-substituering af en forbindelse med den almene formel Ibla where X, Y, Ζ, Μ, t, R and R 'are as defined above by N-substituting a compound of general formula Ib

Ib hvor X, Y, Z, M, t og R er som defineret ovenfor, med en gruppe A, der er som defineret ovenfor, ved N-alkylerings-teknikker, og deres anvendelse til bekæmpelse af ukrudt.Ib where X, Y, Z, M, t and R are as defined above, with a group A as defined above by N-alkylation techniques and their use in controlling weeds.