Note: Descriptions are shown in the official language in which they were submitted.
2(~ ~2~3~
- 1 - O.Z. 00~0/41896
2~AnilinocvanopYridines and the use thereof
for controllinq pest~
The present invention r21ates to methods for
controlling pests, which comprise treating the pests
S and/or their habitat with an effective amoun~ of a
2-anilinocyanopyridine of the formula I
CN
02N Rl
~NR 4~R 2
Xm
where
X is nitro; Gyano; halogen; C1-C4-alkyl/ C1-C4-halo-
alkyl; C1-C4-alkoxy; C3-C6-cyClOalkyl; C1-C4-alkylsul-
fonyl; phenyl, phenoxy or phenylthio, it being
possible for the ~romatic groups in turn to carry
from one to five halog~n atoms and/or one to three
of ~he following: C1-C4-alkyl, Cl-C4-haloalkyl, Cl-C,,-
alkoxy, Cl-C4-haloalkoxy, Cl-C4-alkylthio and Cl-Cb-
haloalkylkhio;
m i 1, 2 or 3, it heing pos3ible for the radicals to
be different when m is 2 or 3;
~1 i8 hydrogen; halogen; Cl-C4-alkyl; C1-C4-haloalkyl;
Cl-C4-alkoxy; C~C4-haloalkoxy; pheno~y or phenylthio~
it being possible for the aromatic groups in turn to
-car~y from one to five halogen atoms and/or one to
three of the following: C1-C4-alkyl, C1-C4-haloalkyl,
Cl-C~-alkoxy, Cl-C4-haloalko~y, Cl-C4-alkylthio and
C1-C4-haloalkylthio;
R2 and R3 are each, independently of one anotherl
hydrogen; nitro; cyano, carboxyl; halogen; C1-C6-
alkyl; C1-C8-haloalk~l; C1-C4-al3coxy; C1-C"-haloalkoxy;
C1-C4-alky~thio; Cl-C4-haloalkylthio; Cl-C4-al]co~y-
carbonyl; C1-C4-alkylaminocarbonyl; di-Cl-C4-alkyl-
aminocarbonyl; C1-C4-alkyl~ulfonyl; C1-C4-alkylamino-
~ul0nyl;.di-Cl-C4-alkylaminosulorlyl;
., .
::
,
` 2~2~8
.
- 2 - O.Z. 0050/41896
R4 is hydrogen; formyl; C1-C6-alkyl; C1~C~-haloalkyl;
C3-C6-alkenyl; C3-C8-alkynyl; benzyl which in turn can
carry from one to five halogen a~oms and/or one to
three of the following: Cl-C4-alkyl, Cl-C4-haloalk~l,
C1-C4~alkoxy, Cl-C4-haloalkoxy, Cl-C4-alkylthio and
C1-C4-haloalkylthio;
CoR5 or SO2R8 where
R5 is Cl-C6-alkyl; C1-C~-haloalkyl; C1~C4 alkoxy; C1-C4-
haloalkoxy; C1-C4-alkylthio; C1-C4-haloalkylthio;
Cl-C4-alkylamino;di-C1-C4-alkylamino;benzyl,benzyl-
oxy, benzylthio or benzylamino, it being possible
for the aromatic groups in turn to carry from one to
five halogen atoms and/or one to three of the
following: Cl-C4-alkyl, Cl-C4-haloalkyl, Cl-C4-alkoxy,
C1-C4-haloalkoxy, Cl-C4-alkylthio and Cl-C4-haloalkyl-
thio; and
R6 is C1-C6-alkyl; Cl-C6 haloalkyl, phenyl or benzyl, it
being possible for the aromatic groups in turn to
carry from one to five halogen atoms and~or one to
three of the following: Cl-C4-al~yl, Cl-C4-haloalkyl,
Cl-C4-alkoxy, Cl-C4-haloalkoxy, Cl-C4-alkylthio and
Cl-C4-haloalkylthio,
and ~he salts thereof which can be used in agriculture
and to the use of these compounds.
The 2-anilinocyanopyxidines of the formula I
defined above are disclosed as fungicides in
DE-A 39 25 238~ Also de~cribed in the literature are 2-
anilinopyridines with fungicidal and insecticidal prop~er
tie~ (~P-A 31 ~57).
It i~ an ob~ect of ~he pre~ent in~ention to ~ind
novel methods for controlling insects.
We have now found that thi~ ob~ect i~ achieved by
the method using the 2-anilinocyanopyridines of the
fonmula I de~ined above.
The compound~ I are obtained, ~or example, by the
proce~es da~cribed in the liter ture cited above. With
a view to the intended use of the compounds I, suitable
'
- 3 - O.Z. 0050/~1896
substituents are the following:
X nitro; cyano;
halogen such as ~luorine, chlorine, bromine and
iodine, preferably fluorine, chlorine and bromine,
especially chlorine and bromine;
C1-Cq-alkyl such as methyl, ethyl, propyl, l-methyl-
ethyl, butyl, l-methylpropyl, 2-methylpropyl and
1,1 dimethylethyl,preferably C1-C3-alkyl,especially
methyl, ethyl and l-methylethyl;
Cl-C4-haloalkyl, especially Cl-C2-haloalkyl such as
chloromethyl, dichloromethyl, trichloromethyl,
fluoromethyl, difluoromethyl, trifluoromethyl,
chloro~luoromethyl, dichlorofluoromethyl, chlorodi-
fluoromethyl, l-fluoroethyl, 2-fluoroethyl, 2/2-
di1uoroethyl, 2,2,2-trifluoroethyl, 2-chloro--2
fluoroethyl, 2~chloro-2,2-difluoroethyl, 2,2-di-
chloro-2-fluoroethyl, 2,2,2-trichloroethyL and
pentafluoroethyl, preferably chloromethyl, dichloro-
methyl, trichloromethyl, trifluoromethyl and penta-
fluoroethyl, e~pecially trifluoromethyl;
Cl-C4-alko~y such a~ methoxy/ ethoxy, propoxy, 1~
methylethoxy, butoxy, l-methylpropo~y, 2-methylpro-
po~y and l,1-dimethylethoxy, preferably C1-C3-alkoxy,
especially methoxy and ethoxy;
C3-C~-cycloalkyl ~uch as cyclopropyl, cyclobutyl,
cyclopentyl and cyclohe~yl, especially cyclopropyl;
- C1-C4-alkylsulfonyl ~uch a~ methylsulfonyl, ethylsul~
fonyl, propylsulfonyl, 1-methyl~thylsulfonyl,
butylsulfonyl, l-methylpropylsulfonyl, 2 methylpro-
pylsulfonyl and l,1-dimethylethylsulonyl, prefer-
ably C1-C3-alkylsulfonyl, esp0cially methylsulfonyl;
phenyl, phenoxy or phenylthio, it being possible for
th~ aromatic groups in turn to carry from one to
five halogen atom~ such as ~luorine, chlorine,
bromine and iodine, preferably fluorine, chlorine
and brom.ine, e~pecially chlorine;
andtor one to three of the following:
2 ~
- 4 - O.Z. 0050/41896
Cl-C4-alkyl such as methyl, ethyl, propyl, 1-methyl-
ethyl~ butyl, 1-methylpropyl, 2-methyl~ropyl and
l,l-dimethylethyl/ preferablyCl-C3~alkyl, especially
methyl;
Cl-C~-haloalkyl, especially Cl-C2-haloalkyl such as
chloromethyl, dichloromethyl, trichloromethyl,
fluoromethyl, difluoromethyl, trifluoromethyl,
chlorofluoromethyl, dichlorofluoromethyl, chlorodi-
fluoromethyl, l~fluoroethyl, 2-fluoroethyl, 2,2-
difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-
fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-di~
chloro-2-fluoroethyl, 2,2,2-trichloroethyl and
pentafluoroethyl, especially trifluoromethyl;
C1-C4~alkoxy such as methoxy, ethoxy, propoxy, 1-
methylethoxyt butoxyr 1-methylpropoxy, 2-methyl.pro-
poxy an~ 1,1-dimethylPthoxy, especially methoxy and
e~hoxy;
C~-C4-haloal]coxy, especially C1-C2-haloalkoxy such as
chloromethoxy, dichlorometho~y, trichloromethoxy,
fluorometho~y, di~luoromethoxy, trifluoromethoxy,
chlorofluoromethoxy, dichlorofluoromethoxy, chloro-
difluoromethoxy, 1-fluoroethoxy, 2~fluoroethoxy,
2,2-di~lu~rvethoxy,2,2,2-trifluoroethoxy,2-chloro-
2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-
~5 dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy and
pentafluoroethoxy, preferably trichloxomethoxy and
~rifluorometho~y;
C1 C4-alkylthio 3uch as methylthio, ethylthio,
propylthio, l-methylethylthio, butylthio, l-methyl-
propylthio, 2-methylpropylthio and l,l-dimethyl-
ethylthio, preferably methylthio and ethylthio;
and Cl C4 haloal~ylthio, especially Cl~C2-haloalkyl-
thio such a~ chloromethylthio, dichloromethylthio,
trichlorometh~lthio, fltloromethylthio, difluoro-
methylthi.o,trifluoromethylthio,chlorofluoromethyl-
thio, dichlorofluoromethylthio, chlorodifluoro-
methylthio, 1-fluoroethylthio, 2-fluoroethylthio,
~ 1 2 ~ ~
- 5 - O.Z. 0050/41896
2,2-difluoroethylthio, 2,2,2-trifluoroethylthio,
2-chloro-2-fluoroethylthio, 2 chloro-2,2-difluoro-
ethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-
trichloroethylthio and pentafluoroethylthio,
especially trifluoromethylthio;
m l, 2 or 3, it being possible for the radicals to be
different when m is 2 or 3;
R1 hydrogen;
halogen such as fluorine, chlorine, bromine and
iodine, preferably fluorine, chlorine and bromine,
especially fluorine and chlorine;
Cl-C4-alkyl such as methyl, ethyl, propyl, 1-methyl-
ethyl, butyl, 1-methylpropyl, 2-methylpropyl and
l,1-dimethylethyl, especially methyl;
Cl-C4-haloalkyl, especially Cl~C2-haloalkyl such as
chloromethyl, dichloromethyl, trichlorom0thyl,
fluoromethyl, difluoromethyl, trifluoromethyl,
chlorofluoromethyl, dichlorofluoromethyl, chlorodi-
fluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2 r 2 ~
difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-
fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-di-
chloro-2-fluoroethyl, 2,2,2~trichloroethyl an~
pentafluoroethyl, especially trifluoromethyl;
Cl-C4-alkoxy such as methoxy, etho~y, propo~y,
l-methylethoxy, butoxy, l~methylpropoxy, 2~methyl-
propoxy and l,l-dimethylethoxy, preferably
C1-C3-alkoxy, especially methoxy and etho~y;
Cl-C4-haloalko~y, especially C1-C2-haloalkoxy such as
chloxomQtho~y, dichloromethoxy, trichloromethoxy,
fluoromethoxy, difluoromstho~y, trifluoromethoxy,
chlorofluoromethoxy, dichlorofluoromethoxy, chloro-
d~fluorometho~y, .L-fluoroetho~y, 2-fluoroethoxy,
2,2-difluoroethoxy,2,2,2-trifluoroethoxy,2-chloro-
2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-
3S dichloro-2-fluoroethoxy, ~,2,2-trichloroethoxy and
penta~luoroethoxy, especially trifluoromethoxy;
pheno~y or phenylthio, it being pos~ible for the
, " ~
., ~
2 ~
- 6 - O.Z. 0050/41896
aromatic groups in turn to carry from one to five
halogen atoms such as fluorine~ chlorine, bromine
and iodine, preferably fluorine, chlorine and
bromine, especially fluorine and chlorine;
and/or one to three of the following:
Cl-C4-alkyl such as methyl, ethyl, propyl, 1-methyl-
ethyl, butyl, 1-methylpropyl, ~-methylpropyl and
1,1-dimethylethyl, especially m~thyl;
Cl-C4-haloalkyl, especially C1-C~-haloalkyl such as
chloromethyl, dichloromethyl, trichloromethyl,
fluoromethyl, di f luoromethyl, trifluoromethyl,
chlorofluoromethyl, dichlorofluoromethyl, chlorodi~
fluoromethyl, l-fluoroethyl, 2-fluoroethyl, 2,2-
difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-
fluoroathyl, 2-chloro-2,2-difluoroethyl, 2,2--di-
chloro-~-fluoroethyl, 2,2,2-trichloroethyl and
penta~luoroethyl, especially tri1uoromethyl;
C1-C4-alkoxy such as methoxy, ethoxy, propoxy, 1-
methyletho~y, butoxy, l-methylpropoxy, 2-methylpro-
poxy and 1,1-dLme~hylethoxy, especially methoxy and
ethoxy;
Cl-C4-halQalkoxy, e3p~cially C1-C2-haloalkoxy such a~
chloxomethoxy, dichlorvmethoxy, tr~chloromethoxy,
fluoromethoxy, difluoromethoxy, trifluoromethoxy,
chl~rofluorom~tho~y, dichlorofluoromethoxy, chloro-
di~luoromethoxy, 1-~luoroethoxy, 2-fluoroethoxy,
2,2-difl-loroetho~y,2,2,~-trifluoroethoxy,2-chloro-
2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,~-
diehloro-2-1uoroethoxy, 2,2,2-trichloroethoxy and
30 - panta~luoroethoxy, espeeially trifluorQmetho~y;
Cl-C4-alkylthio such a~ methylthio, e~hylthio,
propylthio, 1 methylethylthio, butylthio, l-methyl-
propylthio, 2-methylpropylthio and l,1-dimethyl-
ethylthio, especially methylthio and el;hyl~hio;
and Cl-C4-haloalkylthio, e~pecially Cl-C2-haloal~yl-
thio such a~ chloromethylthio, dichloromethylthio,
trichloromethylthio, fluoromethylthio, difluoro-
-~
.
. ~.
~ 2 ~ $
- 7 - O.Z. 0050/41896
methylthio,trifluoromethylthio,chlorofluoromethyl-
thio, dichlorofluoromethyl~hio, chlorodifluoro-
methyl~hio, 1-fluoroethylthio, 2-fluoroethylthio,
2,2~difluoroethylthio, 2,2,2--trifluoroethylthio, 2-
chloro 2-fluoroethylthio, 2-chloro-2,2-difluoro-
ethylthio, 2,2-dichloro~2~fluoroe~.hylthio, 2,2 t 2-
trichloroethylthio and pentafluoroethylthio, espe-
cially trifluoromethylthio;
R2 and R3, independently of one another, hydrogen;
nitro; cyano; carboxyl;
halogen such as fluorine, chlorine, bromine and
iodine, preferably fluorine/ chlorine and bromine,
especially fluorine and chlorine;
Cl-C6-alkyl such as methyl, ethyl, propyl, 1-methyl-
ethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-
dLmethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl,
3-methylbutyll 2,2-climethylpropyl/ l-ethylpropyl,
he~yl, l,1-dLmethylpropyl, 1,2-dimethylpropyl,
m~thylpentyl, 2~methylpentyl, 3-methylpentyl r 4~
methylpentrl, l,l-dLmethylbutyl, 1 r 2-dLmethylbutyl,
1,3-dLmethylbutyl, 2,2-dimethylbutyl, 2,3-dimethyl-
butyl, 3,3-dLme~hylbutyl, 1-ethylbutyl, 2-ethyl-
butyl,l,l,2-trLmethylpropyl,1,2,2-trLmethylpropyl,
l-ethyl-1-methylpropyl and 1-ethyl-2-m~thylpropyl,
preferably C1-C4-alkyl, especially methyl, ethyl, 1-
methylethyl, l-methylpropyl and 1,l~dimethylethyl;
Cl-C4-haloalkyl, especially Cl-C2-haloalkyl ~uch as
chloromethyl, dichloromethyl, trichloromethyl,
fluoromethyl, difluoromethyl, tri~luoramethyl,
chlorofluoromethyl, dichlorofluoromethyl, chlorocli-
fluoromethyl, 1 1uoroethyl, 2-fluoroethyl, 2,2-
difluoroethyl, 2,2,2-tri~luoroethyl, 2-chloro-2-
fluoroeth~l, 2-chloro-2,2-difluoroethyll 2,2-di~
chloro-2-fluoroethyl, 2,2,~ trichloroethyl and
penta~luoroethyl, preerably tri~luoromethyl and
trichloromathyl t especially ~rifluoromethyl;
Cl~C4 alkoxy such as me~hoxy, ethoxy, propo~y,
:' ~
2~12~ `
- 8 - O.Z. 0050/41896
1-methylethoxy, butoxy, l~methylpropoxy, 2-methyl-
propoxy and l,1-dimethylethoxy, preferably Cl-C3-
alkoxy, especially methoxy and ethoxy;
Cl C4-haloalkoxy especially Cl-C2-haloalkoxy such as
chloromethoxy, dichloromethoxy, trichloromethoxy,
fluorome~hoxy, difluoromethoxy, trifluoromethoxy,
chlorofluoromethoxy, dichlorofluorom2thoxy, chloro-
di f luoromethoxy, 1-fluoroethoxy, 2-fluoroethoxy,
2,2-difluoroethoxy,2,2,2-trifluoroethoxy,2-chloro-
2-fluoroethoxy~ 2-chloro-2,2-difluoroethoxy, 2,2-
dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy and
pentafluoroethoxy, especially trifluoromethoxy;
Cl-C4-alkylthio such as methylthio, ethylthio,
propylthio, l-methylethylthio, butylthio, l-methyl-
propylthio, 2-methylpropylthio and l,1-dimethyl-
ethylthio, preferably Cl-C3-alkylthio, especially
methylthio and ethylthio;
and Cl-C4-haloalkylthio, e~pecially Cl-C2-haloalkyl-
thio such as chloromethylthio, dichloromethylthio,
trichloromethylthio, fluoromethylthio, difluoro-
methylthio,trifluoromethylthio,chlorofluoromethyl-
thio, dichlorofluoromethylthio, chlorodifluoro-
methylthio, 1-fluoroethylthio, 2-fluoroethylthio,
2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-
chloro-2-fluoroethylthio, 2-chloro--2,2-difluoro-
ethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-
~richloroethylthio and pentafluoroe~hylthio,
e~pecially trifluoromethylthio;
Cl-C4-alkoxycarhonyl such a~ mathoxycarbonyl, ethoxy-
carbonyl, propoxycarbonyl, l-methylethoxycarbonyl,
butoxycarbonyl, l-methylpropoxycarbonyl, 2-methyl-
propoxycarbonyl and 1,1-dimethylethoxycarbonyl,
preferably C1~C3 alkoxycarbonyl, especially methoxy-
carbonyl and ethoxycarbonyl;
Cl-C4 alkylaminocarbonyl such as methylaminocarbonyl,
ethylaminocarbonyl, propylaminocarbonyl r 1-methyl
ethylaminocarbonyl, butylaminocarbonyl, l-methyl-
. : -
.:
~ ~,
2 ~ ~
- 9 - O.Z. 0050/41%96
propylaminocaxbonyl, 2-methylpropylaminocarbonyl,
1,1-dimethylethylaminocarbonyl, pentylaminocarbonyl,
l-methylbutylaminocarbonyl, 2-methyl~utylamino-
carbonyl, 3-methylbutyl~ninoca.rbonyl, 2,2-dimethyL-
S propylaminocarbonyl, 1-ethylpropylaminocarbonyl,
hexylaminocarbonyl, 1,1-dimethylpropylaminocarbonyl,
1,2-dimethylpropylaminocarbonyl, l-methylpentyl-
aminocarbonyl, 2-methylpentylaminocarbonyl, 3
methylpentylaminocarbonyl, 4-methylpentylamino-
carbonyl, l,l-dimethylbutylaminocarbonyl, 1,2-
dimethyl~utylaminocarbonyl, 1,3-dimethylbutylamino-
carbonyl r 2,2-dimethylbutylaminocarbonyl, 2,3-
dimethylbutylaminocarbonyl, 3,3-dimethylbutylamino-
carbonyL, l-ethylbutylaminocarbonyl, 2-ethylbut:yl-
aminocarbonyl, 1,1,2-trLmethylpropylaminocarbonyl,
1,2,2-trimethylpropylaminocarbonyl, l-ethyl~l-
methylpropylaminocarbonyl and 1 ethyl-2-methyl-
prvpylaminocarbonyl, preferably Cl-C3-alkylamino-
carbonyl, e~pecially C1-C2-alkylaminocarbonyl;
di-Cl-C4-alkylaminocarbonyl ~uch as N,N-dimethyl-
aminocarbonyl, N,N-diethylaminocarbonyl, N,N-di-
propylaminocaxbonyl, N,N-di(l-methylethyl)amino-
carbonyl,N,N-dibutylaminocarbonyl,N,N-di(l-methyl-
propyl)~ninocarbonyl, N,N-di(2-methylpropyl)~mino-
carbonyl, N,N-di(l,l-dimethylsthyl)aminocarbonyl,
N-ethyl -N-me thylaminocarbonyl r N-metllyl~N-prQpyl -
. aminocarbonyl,N-methyl-N-(1-methylethyl)amino-
carbonyl, N butyl-N-methylaminocarbonyl, N-methyl-
N-(1-methylpropyl)aminocarbonyl, N-methyl-N-(2-
3n methylpropyl)aminocarbonyl, N-(l,1-dimethylethyl)-
N~methylaminocarbonyl, N-ethyl-N-propylamino-
carbonyl,N-ethyl-N-(1-mQthylethyl)aminocarbonyl,N-
butyl-N-ethyl~ninocarbonyl, N-ethyl-N-(l-methyl-
propyl)aminocarbonyl, N~e~hyl-N-(2-methylpropyl)-
aminocarbonyl, N-ethyl-N-(l,l-dimethylethyl)amino-
carbonyl, N-(l-methylethyl)-N-propylaminocarbonyl,
N-butyl-N-propylaminocarbonyl, N-(l-me~hylpropyl)~
'
. .
:- :
.
`
- 10 -
N-propylaminocarbonyl, N-(2-methylpropyl)-N-propyl-
aminocarbonyl, N-(1,1-dimethylethyl)-N-propyl-
aminocarbonyl, N-butyl-N-(1-methylethyl)amino-
carbonyl, N-(1-methylethyl)-N-(1-methylpropyl)-
aminocarbonyl, N-(1-methylethyl)-N-(2-methylpropyl)-
aminocarbonyl, N-(1,1-dimethylethyl)-N-(1-methyl-
ethyl)aminocarbonyl, N-butyl-N-(1-methylpropyl)-
aminocarbonyl, N-butyl-N-(2-methylpropyl)amino-
carbonyl, N-butyl-N-(1,1-dimethylethyl)amino-
carbonyl, N-(1-methylpropyl)-N-(2-methylpropyl)-
aminocarbonyl, N-(1,1-dimethylethyl)-N-(1-methyl-
propyl)aminocarbonyl and N-(1,1-dimethylethyl)-N-(2-
methylpropyl)aminocarbonyl, preferably di-C1-C2-
alkylaminocarbonyl, especially dimethylamino-
carbonyl;
C1-C4-alkylsulfonyl such as methylaminosulfonyl,
ethylaminosulfonyl, propylaminosulfonyl, 1-methyl-
ethylaminosulfonyl, butylaminosulfonyl, 1-methyl-
propylaminosulfonyl, 2- methylpropylaminosulfonyl,
1,1-dimethylethylaminosulfonyl, pentylaminosulfonyl,
1-methylbutyl aminosulfonyl, 2-methylbutylamino-
sulfonyl, 3-methylbutylaminosulfonyl 2,2-dimethyl-
propylaminosulfonyl, 1-ethylpropylaminosulfonyl,
hexylaminosulfonyl, 1,1-dimethylpropylaminosulfonyl,
1,2-dimethylpropylaminosulfonyl, 1-methylpentyl-
aminosulfonyl, 2-methylpentylaminosulfonyl, 3-
methylpentylaminosulfonyl, 4-methylpentylamino-
sulfonyl, 1,1-dimethylbutylaminosulfonyl, 1,2-
dimethylbutylaminosulfonyl, 1,3-dimethylbutylamino
sulfonyl, 2,2-dimethylbutylaminosulfonyl, 2,3-
dimethylbutylaminosulfonyl, 3,3-dimethylbutylamino
2~ 2~
~ O.Z. 0050/~1896
sulfonyl, 1-ethylbutylaminosulfonyl, 2-ethylbutyl-
aminosulfonyl, 1,1,2-trimethylpropylaminosulfonyl,
1,2,2-trime~hylpropylaminosulfonyl, 1-ethyl~1-
methylpropylaminosulfonyl and 1-ethyl-2-methyl-
propylaminosulfonyl, preferably Cl-C3-alkylaminosul-
fonyl, especially methylaminosulfonyl;
di-C1-C4-alkylaminosulfonyl such as N,N-dLmethy].-
aminosulfonyl, N,N-diethylaminosulfonyl, N,N-di-
propylaminosulfonyl, N~N-di(1-methylethyl)amino-
sulfonyl,N,N-dibutylaminosulfonyl,N,N--di(1-methyl-
propyl)aminosulfonyl, N,N-di~2-methylpropyl)amino~
sulfonyl, N,N-di(1,1-dimethylethyl)aminosulfonyl,
N-ethyl-N-methylaminosulfon~l, N-methyl-N~propyl-
am~nosulfonyl, N methyl-N~ methylethyl)amino-
lS sulfonyl, N-butyl-N-methylaminosulfonyl, N-methyl-
N-(1-methylpropyl)aminosulfonyl~ N-methyl-N-(2-
methylpropyl)aminosulfonyl, N-(1,1-dimethylethyl)~
N-me~hylaminosulfonyl, N~ethyl-N-propylamino-
sulfonyl,N-ethyl-N~ methylethyl)aminosulfonyl,N-
butyl-N-~thylaminosul~onyl, N-ethyl-N-(1-methyl
propyl)aminosulfonyl~ N-ethyl-~-(2-me~hylpxopyl)-
amino~ulfonyl, N-ethyl~N-(1,1-dimethylethyl)amino-
sulfonyl, N-(1-methylethyl)-N-propylaminosulfonyl,
N-butyl-N propylamino~ulfonyl, N-(1-methylpropyl)-
N-propylaminosul~onyl, N-(2-methylpropyl)-N-propyl-
aminosulfonyl, N-~ dimethylethyl)-~-propylami:no-
. ~ulfonyl, N-butyl-N-~l-methylethyl)aminosulfonyl,
N-~1-methylethyl~-N-~l-me~hylpropyl)aminosulfonyl,
N~(1 methylethyl)-N-(2-methylpropyl)aminosulfonyl~
N-(l,l-dimathylethyl) N-(1-methylethyL)aminosul-
fonyl, N-butyl-N (1-methylpropyl)aminosulfonyl, N-
butyl-N-(2-methylpropyl)aminosulfonyl, ~-butyl-N-
(1,1-dimethylethyl)aminosulfonyl, N~ methyl-
propyl)-N-(2-methylpropyl)aminosulfonyl, N-(l,1-
dimethylQthyl)-~-(1-methylpropyl)aminosulfonyl and
N-(1,1-dimethylethyl)-N-(2-methylpropyl)aminosul-
fonyl, especially dimethylaminosulfonyl;
- . . . : ~ , .
. - . : ': ;
` ` 2031298
~ O.Z. 0050/41896
R4 hydrogen; formyl;
CL_C6_a1kY1 such as methyl, ethyl, propyl, l-methyl-
ethyl, butyl~ 1-methylpropyl, ~-methylpropyl, 1,1-
dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl,
3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl,
hexyl, 1,l-dimethylpropyl, 1,2-dimethylpropyl~ 1-
methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-
methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl,
1,3-dlmethylbutyl, 2,2-dimethylbutyl, 2,3-dimethyl-
butyl, 3,3-dLmethylbutyl, l-ethylbutyl, 2-ethyl-
~utyl,1,1,2-trimethylpropyl,1,2,2-trimethylpropyl,
l-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl,
preferably Cl-C4 -alkyl, especially Cl-C2-alkyl;
Cl-C6-haloalkyl, espe ially Cl~C4~haloalkyl, in
par~icular Cl-C2-haloalkyl such a~ chloromethyl,
dichloromethyl, trichloromethyl, fluoromethyl,
difluvxomethyl,trifluoromethyl,chloro~luoromethyl,
dichlorofluoromethyl, chlorodifluorome~hyl, 1-
fluoroethyl, 2-fLuoroethyl, 2,2-difluoroethyl,
2,2,2-~ri~luoroethyl, 2-chloro-2-fluoroethyl, 2-
chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoro-
ethyl, 2,2,2~trichloroethyl and pentafluoroethyl,
preferably trifluoromethyl, 2,2,2-trichloroe~hyl and
2,2,2-trifluoroethyl;
C3-C6-alkenyl such as 2-propenyl, 2-butenyl, 3-
butenyl, 1-methyl-2-propenyl, 2-me~hyl-2-propenyl,
2-pentenyl, 3-pentenyl, 4-pen~enyl,
1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-
butenyl, l-methyl-3-butenyl, 2-methyl-3-but2nyl,3-
methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-
dimethyl-2-propenyl, 1-ethyl-2-propenyl, 2-hexenyl,
3-hexenyl, 4-hexanyl, 5-hexenyl, 1-methyl-2-pen-
tenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-
methyl-2-pentenyI, l-methyl-3-pentenyl, ~-methyl-3-
pentenyl, 3~methyl-3 pentenyl, 4-methyl-3-pentenyl,
l-mathyl-4-pentenyl, 2~methyl~4 pentenyl, 3-methyl-
4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-
. .
~ ' ; ' ' , :
: . : ' ' ,~-. '
2 ~ ~
- 13 - O.~. 0050/~1896
butenyl, l,l-dimethyl-3-butenyl, 1,2-dimethyl-2-
butenyl, 1,2-dLmethyl-3-butenyl, 1,3-dimethyl-2-
butenyl, 1,3-dimethyl-3-but~nyl, 2,2-dime~hyl-3~
butenyl, 2,3-dimethyl 2-butenyl, 2,3-dimathyl-3-
S butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-2-butenyl,
l-ethyl-3-butenyl, 2-ethyl~2-butenyl, 2-ethyl-3-
butenyl, l,l,~ctrimethyl-2-prope~yl r l-et.hyl~l-
methyl-2 propenyl and 1-ethyl-2-methyl-2-propenyl;
pref~rably C3-C4-al]cenyl, especially 2 propenyl, 2-
butenyl and 3-butenyl;
C3-C6-al~rnyl such as 2 propynyl, 2-butynyl, 3-
butynyl, l-methyl-2-propynyl, 2-pentynyl, 3-pen-
tynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-
butynyl, 2-methyl 3~but~nyl, 1,1-dimethyl-2-pro-
pynyl, 1-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4-
he~ynyl, 5-hexynyl, 1-methyl-2-pentynyl, l-n~ethyl-
3-pentynyl, 1-methyl-4 pentynyl, 2-methyl-3-pen-
tynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 4-
methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-
dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-
dimethyl~3-butynyl, 1-ethyl~2~butynyl, 1 ethyl-3-
butynyl, 2-ethyl-3~butynyl and 1-ethyl-1-methyl-2-
propynyl; pre~erably C3-C4-alkynyl, especially 2-
propynyl;
benzyl which in turn can carry from one to f:ive
halogen atom~ such a~ fluorine, chlorine, brom:ine
- and iodine, preferably fluorine and chlorine~
and/or one to three of the following:
C1-C4-alkyl such a~ methyl, ethyl, propyl, l-methyl-
ethyl, butyl, 1-methylpropyl, 2 methylpropyl and
l,l-dimethylethyl, preferably C1-C2-aLkyl, especially
methyl;
C1-C4-haloalkyl, especia].ly C1-C2-haloalkyl such a~
chloromethyl, dichloromethyl, trichloromethyl,
fluoromethyl, difluoromethyI, trifluoromethyl,
chlorofluoromethyl, dichlorofluoromethyl, chlorodi~
fluoromet~yl, l-fluoroethyl, 2 ~luoroethyl~ 2,~-
.
- . .: , . . : , , ,
',. ' . - ' ' . ' :
. . ,, ~ '
2 ~ 2 ~ $
- 14 - O.z. 0050/41~96
difluoroethyl, 2,2,2 trifluoroethyl, 2-chloro-2-
fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-di-
chloro-2-fluoroethyl r 2,2,2-trichloroethyl and
pentafluoroethyl, preferably tri-fluoromethyl;
Cl-C4 alkoxy such as methoxy, ethoxy, propoxy, 1-
methylethoxy, butoxy, l-methylpropo.xy, 2-methylpro-
poxy and 1,1-dimethyletho~y, preferably methoxy and
ethoxy;
Cl-C4-haloalkoxy, especially Cl-Cz-haloalkoxy such as
chloromethoxy, dichloromethoxy, txichloromethoxy,
fluoromethoxy, difluoromethoxy, txifluoromethoxy,
chlorofluoromethoxy, dichlorofluoromethoxy, chloro-
difluoromethoxy, l-fluoroethoxy, 2-fluoroetho~,
2,2-difluoroethoxy,2,2,2-trifluoroe~hoxy,2-chloro-
2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2~2-
dichlo~o-2 fluoroethoxy, 2,2,2 trichloroethoxy and
penta1uoroethoxy, e~pecially tri~luorometho~y;
C1-C4-alkylthio such as methylthio, ethylthio,
propylthio, 1-methylethylthio, butylthio, l-methyl-
propylthio, 2-methylpropylthio and 1,1-dimethyl-
ethylthio, especially methylthio and ethylthio;
and Cl C4-haloalkylthio, especially C~-C2-haloalkyl-
thio such a~ chloromethylthio, dichloromethylthio,
trichloromethyl~hio, fluorome~hylthio, difluoro-
25 . methylthio,tri~luoromethylthio,chlorofluoromethyl-
thio, dichlorofluoromethylthio, chlorodifluoro-
methylthio, 1-fluoroethylthiQ, 2-fluoroethylthio~
2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-
chloro-2-~luoroethylthio, 2-chloro-2, 2-dif luoro~
ethyl~hio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-
trichloroethylthio and pentafluoroethylthio,
especially trifluoromethylthio;
R' i~ also CoR5 or SO2R6 where R5 is
C1-C6-alkyl such as methyl, ethyl, propyl, 1-methyl~
eth~l, butyl, l-methylpropyl, ~-methylpropyl, 1,1-
dimethylethyl, pentyl, 1-methylbutyl, 2-mathylbutyl,
3-mathylbutyl, 2,2-dimethylpropyl r 1-ethylpropyl,
'
2 ~
- 15 - O.Z. 0050/418g6
hexyl, l,1-dimethylpropyl, 1,2-dimethylpropyl, 1-
methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-
methylpentyl, 1,l~dimethylbutyl, 1,2-dimethylbutyl,
1,3 dLmethylbutyl, 2,2-dimethylbutyl, 2,3-dime~hyl-
butyl, 3,3-dimethylbutyl, l-ethylbutyl, 2-ethyl-
butyl,1,1,2-trimethylpropyl,1,2,2--trimethylpropyl,
l-ethyl-l-methylpropyl and l-ethyl 2 methylpropyl,
preferably Cl-C4-`alkyl, especially methyl, ethyl,
propyl and l,l-dimethylethyl;
Cl-C6-haloalkyl~ especially Cl-C4-haloalkyl such as,
in particular, chloromethyl, dichloromethyl, tri-
chloromethyl, fluoromethyl, difluoromethyl, tri-
fluoromethyl, chlorofluoromethyl, dichlorofluoro-
methyl, chlorodifluoromethyl, 1-fluoroethyl, 2-
fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoro-
ethyl, 2-chloro-2-fluoroethyl t 2-chloro~,2-di-
fluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-
trichloroethyl and pentafluoroethyl;
C~-C~,-alkoxy such as methvxy, e-thoxy, propogy, 1-
methyletho~y, butoxy, 1-methylpropoxy, ~-methylpro~
po~y and 1,1-dimethyletho~y, preferably methoxy and
ethoxy;
C1-C4-haloalkoxy, especially Cl-C2-haloalkoxy such as
chloromethoxy, dichloromethoxy, trichloromethoxy,
~luoromethoxy, difluorometho~y, trifluorometho.xy,
chlorofluoromethoxy, dichlorofluoromethoxy, chloro
difluoromethoxy, 1-fluoroetho~y, 2-fluoroethoxy,
2,2-difluoroethoxy,2,2,2-trifluoroethoxy,2-chloro-
2-1uoroethoxy, 2-chloro-2,2-difluoroetho~y, 2,2-
dichloro-2-fluoroethoxy, ~,2,2-trichloroetho~y and
pentafluoroethoxy, especially tri~luorometho~y;
C1~C4-alkylthio such as methylthio, ethylthio,
propylthio, 1-methylethylthio, butylthio, 1-methyl-
propylthio, 2-methylpropylthio and 1 t 1 dimethyl-
3S ethylthio, preferably methylthio and ethylthio;
C1-C"-haloalkylthio, especially Cl-C2-haloalkylthio
such as chloromethylthio, dichloromethylthio,
.. . .
2 ~ ~
- 16 - O.Z. 0050/41896
trichloromethylthio, fluoromethylthio, difluoro-
methylthio,trifluoromethylthio,chlorofluoromethyl-
thio, dichlorofluoromethylthio t chlorodifluoro-
methylthio, l-fluoroeth~lthio, 2-fluoroethylthio r
2,2-difluoroethylthio~ 2,2,2-trifluoroethylthio, 2-
chloro-~-fluoroe~hylthio, 2-chloro-~,2-difluoro-
ethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-
trichloroe~hylthio and pent fluoroethylthio, espe-
cially trifluoromethylthio~
Cl-C4-alkylamino such as methylamino, ethylamino,
propylamino, 1-methylethylamino, butylamino, 1-
methylpropylamino, 2-methylpropylamino, 1ll-di-
methylethylamino, pentylamino, 1-methylbutylamino,
2-methylbutylamino, 3-methylbutylamino, 2,2-di-
methylpropylamino, 1-ethylpropylamino/ he~ylamino,
1,l~dimethylpropylaminQ,1,2-dimethylpropylamino t 1-
methylpentylamino, 2-methylpentylamino, 3-methyl-
pentyl~mino, 4-methylp2ntylamino, 1,1-dimethyl-
butylamino, 1l2-dLmethylbutylamino, 1 t 3-dimethyl-
butyl~mino, 2,2-~imethylbutylamino, 2,3-dimethyl-
bu~ylamino, 3,3-dLmethylbutylamino, l-ethylbutyl-
amino, ~-~thylbutylamino, 1,1,2 trLmethylpropyl-
amino, 1 J 2 ~ 2-trimethylpropylamino, l-ethyl-1-
methylpropylamino and l-e~hyl-2-me~hylpropylamino,
preferably Cl C3-alkylamino, especially C1~C2-alkyl-
amino;
di-Cl-C4-alkylamino such as N,N-dLme~hylamino, N,N-
diethylamino, N,~-dipropylamîno, N,N-di~1-methyl-
ethyl)amino, N,N-dibutylamino, N,N-di(l methyl-
propyl)amino, N, N-di (2-m~thylpropyl)amino, NIN-
di~1,1-dimethylethyl)amino, N-ethyl-N-methylamino,
N-methyl~N-propylamino, N-methyl-N (1-methylethyl)-
amino, N-butyl-N-methylamino, N-methyl-N~ me~hyl-
propyl)amino, N-methyl-N-(2-methylpropyl)amino~ N-
(l,1-dimethyleth~l)-N-methylamino/ N-ethyl-N-propyl
amino, N-ethyl-N-(1-methylethyl)amino, N-butyl-N-
ethylamino, N-ethyl-N (l-methylpropyl)amino, N-
~, ' ~ - . . .
'~
: ' .
2 ~
- 17 - O.Z. 0050/41896
ethyl-N-(2-methylpropyl)amino, N-ethyl-N-(1,1-
dimethylethyl)amino, N~ methylethyl)-N-propyl-
amino, N-butyl-N-propylamino, N-(1-methylpropyl)-N-
propylamino, N-~2-methylpropyl)-N-propylamino, N-
(1,1-dLmethylethyl)-N-propylamino, N-butyl-N-~1-
methylethyl)amino, N~ methylethyl)--N- (1-methyl-
propyl)amino, N-(l-methylethyl)-N-(2-methylpropyl)--
amino, N-(1,1-dimethylethyl)-N-(l-methylethyl)amino,
N-butyl-N-(l-methylpropyl)amino, N-butyl~N-(2-
methylpropyl)amino, N-butyl-N-(l,l~dimethylethyl~-
amino, N-(1-methylpropyl)-N-(2-methylpropyl)amino,
N-(1,1-dLmethylethyl)-N-(l-methylpropyl)aminoanclN-
(l,1-dLmethylethyl)-N-t2-methylpropyl)amino, prefer-
ably di-C1-C2-al~ylamino, especially dimethylamino;
benzyl, benzyloxy, benzylthio or benzylamino, it
be.ing possible for the aromatic groups in turn to
carry from one to five halogen atoms such as fluor-
ine, chlorine, bromine and iodine, preferably
fluorine, chloxine and bromine, especially fluorine
and chlorine;
and/or one to three o~ the following:
Cl-C4-~lkyl such as methyl, ethyl, propyl, l-methyl-
ethyl, butyl, l-me~hylpropyl, 2-methylpropyl and
1,1 dimethylethyl, preferably Cl-C3-alkyl, especially
2 5 Cl-C2-a~
Gl-C4-haloalkyl, especially C1-Cz-haloalkyl such ~s
chloromethyl, dichloromethyl, trichloromethyl,
fluoromQthyl, difluoromethyl, trifluoromethyl,
chlorofluoromethyl, dichloro~luoromethyl, chlorocLi
- fluoromethyl, 1--fluoroethyl, 2-fluoroethyl, 2,2-
difluoroethyl, 2,2,2-trifluoroethyl, 2 chloro~-2-
fluoroethyl, 2 chloro 2,2-difluoroethyl, 2,2-di-
chloro-2-fluoroethyL, 2,2,2-trichloroethyl and
pentafluoroathyl, e~pecially trifluoromethyl;
Cl-C4-alkoxy such as methoxy, ethoxy, propoxy, 1
meth~lethoxy, butoxy, 1-methylpropo~y, 2-methylpro-
poxy and l,1-dimethylethoxy, preferably Cl-C2-alkoxy,
$
- 18 - O.Z. 0050/41896
especially methoxy;
Cl-C4-haloalkoxy, especially Cl C2-haloalkoxy ~uch as
chlorom~thoxy, dichloromethoxy, trichloromethoxy,
fluoromethoxy, difluoromethoxy, trifluoromethoxy,
chlorofluoromethoxy, dichlorofluoromethoxy, chloro-
difluoromethoxy, l-fluoroethoxy, 2-fluoroethoxy,
2,2-di~luoroethoxy,2,2,2-trifluoroethoxy,2~chloro-
2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-
dichloro-2-fluoxoethoxy, 2,2,2-trichloroethoxy and
pentafluoroethoxy, especially trifluorome~hoxy;
C1-C4-alkylthio such as methylthio, ethylthio,
propylthio, 1-methylethylthio, butylthio, 1-methyl-
propylthio, 2-methylpropylthio and 1,1-dimethyl-
ethylthio, pre~rably C1-C2-alkylthio;
and C~-C4-haloalkylthio, especially Cl~C2-haloalkyl-
thio such as chloromethylthio, dichloromethylthio,
trichloromethylthio, fluoxomethylthio, difluo:ro-
methylthio,trifluoromethylthio,chlorofluoromethyl-
thio r dichloro~luoromethylthio, chlorodifluoro-
methylthio, 1-fluoroethylthio, 2-fluoroethylthio,
2,2-difluorosthylthio, 2,2,2~trifluoroethylthio, 2-
chloro-2-fluoroethylthio, 2 chloro-2,2-di1uoro-
ethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-
trichloroethylthio and p~ntafluoroethylthio, espe-
cially trifluerom2thylthio;
and
R~ - s Cl-C~-alkyl ~uch a~ methyl, ethyl, propyl, 1-
methyl~th~l, butyl, l methylpropyl, 2-methylpropyl,
1,l-dimethylethyl, pentyl, l-methylbutyl, 2-methyl-
butyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethyl-
propyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethyl-
propyl, l-methylpentyl, 2-methylpentyl, 3-methyl-
pentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-
dimethylbutyl,1,3-dimethylbutyl,2,2-dimethylbutyl,
2,3-dimethylbutyl, 3,3 dimeth~lbutyl, l-ethylbutyl,
2-ethylbut~rl, 1,1,2-trimethylpropyl, 1,2,2-tri-
methylpropyl, l~ethyl-1-methylpropyl and 1-ethyl-2-
.
`~
2 ~ ~
- 19 - O.Z. 0050/41896
methylpropyl, preferably Cl-C3-alkyl! especially
C~-C2-alkyl;
Cl-C6-haloalkyl,preferablyCl-C4-haloalkyl,especial-
ly Cl-C2-haloalXyl such as chloromethyl, dichloro-
methyl, trichloromethyl, fluoromethyl, difluoro-
methyl, txifluoromethyl, chlorofluoromethyl, di-
chlorofluoromethyl, chlorodifluoromethyl, l-fluoro-
e~hyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-
trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-
2,2-difluoroethyl, 2,2 dichloro-2-fluoroethyl,
2,2,2-trichloroethyl and penta~luoroethyl, pre~er-
ably chloromethyl, trif luoromethyl and
pentafluoroethyl;
phenyl or benzyl, it being possible for the aromatic
groups in turn to carry from one to five halogen
atom~ such as fluorine, chlorine, bromine and
iodine, preferably fluorine, chlorine and bromine,
especially chlorine and bromine;
and/or one to three o~ the following:
Cl-C4-alkyl such as methyl, ethyl, propyl, l-methyl-
ethyl, butyl, l-methylpropyl, 2-methylpropyl and
l,l-dimQthylethyl, preferably Cl-C2-al3cyl, especially
methyl;
Cl-C4-haloalkyl, especially Cl-Cz-haloalkyl such as
chloromethyl, dichloromethyl, trichloromethyl,
fluoromethyl, difluoromethyl, trifluoromethyl,
chlorofluoromethyl, dichlorofluoromethyl, chlorodi-
fluoromethyl, l-fluoroethyl, 2-fluoroethyl, 2/2-
di~luoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-
~luoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-di-
chloro-2-~luoroethyl, ~,2,2-trichloroethyl and
penta~luoroathyl, especially trifluoromethyl;
Cl-C4-alkoxy such a~ methoxy, ethoxy, propoxy, 1-
methylethoxy, buto~y~ 1 methylpxopoxy, 2-methylpro-
poxy and 1,l-dimethylethoxy, preferably Cl-C3-alkoxy,
especially Cl-C2-alkoxy;
Cl-C4-haloalkoxy, especially Cl-C2-haloal]coxy such as
:
2 ~
- 20 - O.Z. 0050/~1896
chloromethoxy, dichloromethoxy, trichloromethoxy,
fluoromethoxy, difluoromethoxy, trifluoromethoxy,
chlorofluoromethoxy/ dichlorofluoromethoxy, chloro-
difluoromethoxy, l-fluoroethoxy, 2-fluoroethoxy,
2,2-dlfluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-
2-fluoroethoxy, 2-chloro-2,2-di:fluoroethoxy, 2,2-
dichloro-2 fluoroethoxy, 2,2~2-tric:hloroethoxy and
pentafluoroethoxy, especially trifluoromethoxy;
Cl-C4-alkylthio such as methylthio~ ethylthio,
propylthio, l-methylethylthio, butylthio, l-methyl-
propylthio, 2-methylpropylthio and l,l-dimethyl-
ethylthio, preferably Cl-C2-alkylthio, especially
methylthio;
and Cl-C4-haloalkylthio1 especially Cl-C2-haloalkyl-
thio such as chloromethylthio, dichloromethylthio,
trichloromethylthio, fluoromethylthio, difluoro-
methylthio, trif luoromethylthio,
chlorofluoromethylthio, dichlorof luoromethylthio,
chlorodifluorome~hylthio, l-fluoroethylthio, 2-
f luoroethylthio, 2, 2-dif luoroethylthio,
2,2,2-trifluoroethylthio, 2-chloro 2-fluoroethyl-
thio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-
2-fluoroethylthio t 2,2,2-trichloroethylthio and
pentafluoroethylthio, especially trifluoromethyl-
thio;
and the sal~s thereof which can be used in agriculture.
Particularly preferred 2-anilinocyanopyridines of
the formula I are those where:
Rl i~ hydrogen or halogen as mentioned above, prefer-
ably fluorine, chlorine and bromine;
R2 and R3 are each, independently of one another,
hydrogen; nitro; cyano;
halogen as mentioned above, preferably fluorine,
chlorine and bromine;
C,-C4-haloalk~l as mentioned above, preferably
trichloromethyl and tri:Eluoromethyl;
C,-C4-alko?cy a~ mentioned above, preferably methoxy,
~. ~
2~2~
21 - O.Z. 0050/41896
ethoxy and propoxy;
or C1-C4-haloalkoxy as mentioned above, preferably
trifluoromethoxy;
R4 is hydrogen; CoR5 or SO2R~ where
R5 is C1-C6-alkyl as mentioned above/ preferably C1-C4-
alkyl, especially C1-C2-alkyl;
Cl-C6-haloalkyl as mentioned above, preferably Cl-C2-
haloalkyl;
C1-C4-alkoxy as mentionecl above, preferably C1-C2-
alkoxy;
Cl-C4-haloalkoxy as mentioned above, preferably
trifluoromethoxy,
Cl-C4-alkylthio as mentioned above, preferably Cl-Cz-
alkylthio;
Cl-C4-haloalkylthio as men~ioned above, preferably
trifluoromethylthio;
C1-~4-alkylamino as mentioned above, preferably C1-C3-
alkylamino, especially Cl-C2 alkylamino;
di-C1 C4-alkylamino as mentioned above, preferably
di-C1-C2-alkylamino;
benzyl, benzyloxy, benzylthio or benzylamino, it
being possible for the aromatic groups in turn to
carry from one to five halogen atom~ as mentioned
above, preferably fluorine, chlorine and bromine;
and/or one to three of the following:
Cl-C4~alkyl a~ mentioned above, preferably C1-C3-
alkyl;
Cl-C4-haloalkyl ~s mentio~ed above, preferably
tri1uoromethy~;
Cl-C4-alkoxy as mentioned above, preferably methoxy
and ethoxy;
Cl-C4~haloalkoxy as mentioned above, preferably
tri~luoromethoxy;
Cl-C4-alkylthio as mentioned above, preferably Cl-C2-
alkylthio;
and C1-C4-haloalkylthio as mentioned above, prefer-
ably trifluoromethylthio;
~ o ~
- 2~ - O.Z. 0050~41896
and
R6 i~ phenyl or benzyl, it being possible for the
aromatic groups in turn to carry from one to
five halogen atoms as mentioned above, preferably
fluorine, chlorine and bromine;
and/or one to three of the following:
C1-Cb~alkyl as mentioned above, preferably C1-C2-
alkyl;
C1-C4-haloalkyl as mentioned above, preferfibly
trifluoromethyl;
Cl-C4 alkoxy as mentioned above, preferably Cl-C3-
alkoxy, especially Cl-C2~alkoxy;
Cl-C4-haloalkoxy as mentioned above, preferably
trifluoromethoxy,
C1-C4-alkylthio as mentioned above, pref~rably C1-C3-
alkylthio;
and Cl-C4-haloalkylthio as mentioned above, prefer-
ably trifluoromethylthio;
and the ~al~s thereof which can be used in agricul-
ture. Particularly preferred 2-anilinocyanopyridines
of the formula I are those where
R1 is hydrogen or halogen a~ mentioned above, prefer-
ably fluorine and chlorine;
R2 a~d R~ are each, independently of one another,
hydrogen; nitro; cyano;
halogen a~ mentioned above, preferably fluorine and
chlorine,
or Cl-C2-haloalkyl a~ mentioned above, preferably
tr.ifluoromethyl;
~4 i~ hydrogen or SO2R8 where
R6 is phenyl which can carry ~rom one to f ive halogen
atoms a~ montioned above, preferably chlorine and
bromine;
and/or one to three o~ the Eollowing:
Cl-C4-alkyl a~ mentioned above, preferably methyl;
Cl--C4-haloalkyl a~ mentioned above, preferably
trifluoromethyl;
.: ~
2 ~
23 - O.Z. 0050/~1896
C1-C4~al]coxy as mentioned above, preferably m~tho~y
and ethoxy;
Cl-C4-haloalkoxy as mentioned above; preferably
trifluoromethoxy;
C1-C4-alkylthio as mentioned above, preferably
methylthio;
and C1-C4-haloalkylthio as mentioned above, prefer-
ably trifluoromethylthio;
and the salts thereof which can be used in agriculture.
Suitable salt~ of the compounds of the formula I
are those which can be used in agriculture, for example
alkali metal salts, especially sodium and potassium
salts, alkaline earth metal salts such a3, in particular,
calcium, magnesium and barium salts, manganese, copp~r,
zinc or iron salts, and ammonium salts such as tetra-
alkyl-, trialkyl-~ dialkyl-, alkyl- and benzyltrialkyl~m-
monium salts, phosphonium and sulfonium salts such as
trialkylsulfonium salts or sulfoxonium salts.
Examples of particularly preferred compounds of
the formula I are listed in ~ables A to D which follow.
.
.
. . ~ - ~ ' . : ' '
- 2~2~
- 24 - o. z . 0050~41895
TABLE A: 3-Cyanopyridine derivatives
CN O2N Rl
~NH~R2 I R4 = H)
R3
m
Xm Rl R2 R3
H C I CF3 N2
H C I CN NO2
H C I COOC2H5 N2
H C I CONH2 N2
H C I COOH NO2
H F CF3 N2 ,.
H OCH3 CF3 NO2
H H CF3 NO2
H H CN NO2
H H Cl NO~
H Cl Cl NO2
H H SO2CH3 N2
H H COOCH3 N2
H H CH3 NO2
H H N2 CF3
H H NO;~ C I
ICI-I 3
H H N2 CHC 2H5
Cl Cl Cl
5-C I C I CF3 NO2
5-C I F CF3 N2
5-CI Br CF3 N2
5-C I CF3 CF3 NO2
S-C 1 OCH3 CF3 NO2
5-C I OC2H5 CF3 NO2
5-C I OC4Hg ( n ~ CF3 ~2
5-C 1 OCF3 CF3 NO2
5-C I OCF2CHF2 CF3 NO2
5-C I OC6H5 CF3 NO2
5-C I SC6H5 CF3 N2
5-CI oC6~14-P-CI CF3 N02
5-CI sc6H4-p-cl c~3 N2
5-C I H CF3 N2
- : : . . ~: .
. . .
- 25 - O. ~ . 0050/41896
TAE~LE A ( continuation )
2 3
Xm R ~ R
5-Cl H H Cl
5-Cl H Br NO2
5-CI H Cl NO2
5-CI H CN NO2
5-CI ~ CONH2 No2
5-Cl H CON(CH3)2 N2
5-CI H COOH NO2
5-CI H COOCH3 No2
5-CI Cl CN NO2
5-CI Cl COOC2Hs ~2
5-CI Cl CONH2 NO2
5-CI Cl COOH NO2
5-CI H 52CH3 No2
5-CI ~ S2~H2 No2
5-CI H 5O2N(CH3)2 No2
5-CI H CH3 No2
5-CI H C(CH313 No2
5-CI H OCF3 No2
S-CI H OCF2CHF2 N2
5-Cl H NO2 CF3
5-CI H NO2 Cl
5-CI H NOz CH3
CH3
5-CI H NO2 CHC2H5
5-CI Cl Cl NOz
5-Cl Cl Cl Cl
5-CI H CF3 H
5-CI Cl H H
5-C~3 Cl C~3 NO2
5-CH3 F CF3 No2
5-CH3 H CF3 N2
5--CH3 H NO2 CF3
S-CH3 H NO2 Cl
5.-CH3 Cl Cl No2
5-CH3 Cl CN N~2
5-CH3 Cl COOC2Hs No2
5-Br Cl CF3 NO2
5-Br Cl CN NO2
S-Br Cl COOC2Hs N2
5-Hr . Cl CONH2 NO2
, ~ :: , , . . ' :
,,
20~2~8
~6 - O. Z . OOSO/41896
TABLE ~ ( continuation )
Xm Rl R2 R3
5-Br F CF3 No2
5-Br OCH3 CF3 NO2
5-Br H CF3 No2
5-8r H . CN NO2
5-Br H Cl NO2
5-Br Cl Cl NO2
5-Br H SO2CH3 No2
5-9r H COOCH3 No2
5-Br H CH3 NO~
5-Br H NO2 CF3
5-Br H NO2 Cl
CIH3
S-Br H NO2 CH-C2H5
5-Br Cl Cl Cl
5-CF3 Cl CF3 NO2
5~CF3 F CF3 NO2
5-CF3 H CF3 N2
S-CF3 H NO2 CF3
5-CF3 H NO2 Cl
5-CF3 Cl Cl N2
5-CF3 Cl CN No2
5-CF3 Cl COOC2H5 No2
6-Cl Cl CF3 N2
6-CI F CF3 No2
6-CI Br CF3 NO2
6-CI CF3 CF3 NO2
6-CI . OCH3 CF3 NO2
6-CI OC~H5 CF3 NO2
6-Cl O-n-C4Hg CF3 NO2
6-CI OCF3 CF3 NO2
6-CI OCF2CHF~ CF3 N2 .
6 Cl OC6H5 C~3 ~2
6-CI SC6H5 CF3 NO2
6--CI OC6H4-p-Cl CF3 NO2
6 Cl SC6H4-p Cl CF3 No2
6-CI H CF3 rlo2
6-CI H H Cl
6-CI H Br NO2
6-Cl H C1 NO2
6-CI H CN NO2
: ;:
2~2~
- 2~ - O.Z. 0050/~1896
TABLE A (continuation)
X Rl R2 R3
m ~
6-CI H CONH2 No2
6-CI H CoN(cH3)2 No2
6-CI H COOH NO2
6-CI H COOCH3 No2
6-CI Cl CN NO2
6-Cl Cl COOC2H5 No2
6-CI Cl CONH2 No2
6-CI Cl COOH NO2
6-CI H SO2CH3 N2
6-CI H S2NH2 No2
6-CI H SO2N~CH3)2 No2
6-CI H CH3 NO2
6-CI H C~CH3)3 No2
6-CI H OCF3 NO2
6-CI H 0CF2CHf2 N2
6-CI H NO2 CF3
6-CI H N2 Cl
6-CI H NO2 CH3
CH3
6-CI H NO2 CH-C2H5
6-CI Cl Cl NO2
6 Cl Cl Cl Cl
6-CI H CF3 H
6-6r Cl CF3 NO2
6-Br F CF3 No2
6-Br H CF3 No2
6-Br H NO2 CF3
6-Br H NO~ Cl
6-Br Cl Cl No2
6-Br Cl CN N02
6-Cr Cl COOC2H~ No2
6-cyclo-C3H~ Cl CFF3 N02
6-cyclo-c3Hs CF No2
6-cyclo-c3H5 H 3
6 cyc lo C3H5 H N02 CF3
6-cyc~o-c3~ls Cl CN02
6-cyc lo-C3Hs Cl
6-CH(CH3\2 Cl CF3 NNOo22
:
., ~ ~. : ` -
2 ~
- 28 - O. Z . 0050/~1~96
TABLE A ( continuation )
~m Rl R2 R3
6-CH(CH3)2 F CF3 No2
6-CH(CH3)2 H CF3 No2
6-CH(CH3)2 H N02 CF3
6-CH(CH3)2 N02 Cl
6-CH(CH3)2 Cl Cl No2
6-CH(CH3)2 Cl CN No2
6-CH(C~13)2 Cl cooC2Hs N2
6-CH3 Cl CF3 N02
6-CH3 F CF3 N52
6-CH3 H CF3 No2
6-CH3 H N02 CF3
6-CH3 H N02 Cl
6-CH3 Cl Cl No2
6-CH3 Cl CN N02
6-CH3 Cl COOC2Hs No2
6-CN Cl CF3 N02
6-CN F CF3 No2
6-CN H CF3 No2
6-CN H N2 CF3
6-CN H N02 Cl
6-CN Cl Cl N02
6-CN Cl CN N02
6-CN Cl COOC2Hs NO~
6-SC6Hs Cl CF3 N02
6-SC6H5 F CF3 No2
6-SC6HS H CF3 No2
6-SC6Hs H N02 CF3
6-SC6H5 H N02 Cl
6-SC6H5 cI c1 N
6-SC6H5 Cl CN N
6-SC6H5 Cl COOC2H5 No
6-SC6~5 Cl CF3 N0
6-SC6HS F CF3 No
6-SC6H5 H CF3 No
6-SC6Hs H N02 CF3
6-SC6~15 H N02 Cl
6-SC6~15 Cl Cl No
6 SC6H5 Cl CN No
6-SC6H5 Cl C00~2~15 N0
6-OC2~5 . Cl CF~ N
2~2~
- 29 - O. Z . 0050/41896
TABLE A (continua~ion)
Xm Rl R2 R3
- ~
6-0C2H5 F CF3 N2
6-OC2H5 H CF3 N2
6-0C2H5 H N02 CF3
6-OC2H5 H N02 Cl
6-0C2H5 Cl Cl N2
6-0C2H5 Cl CN N2
6-OC2H5 Cl cooC2H5 N2
4,6-~CH3)2 Cl Cf3 N2 `.
4,6-(CH3)2 F CF3 N2
4,6-(CH3)2 H CF3 N02
4,6-(CH3)2 H N02 CF3
4,6-(CH3)2 H N02 Cl
4,6-(CH3)2 H C(CH3)3 N2
4,6-tC~3)2 Cl Cl N02
4,6-(CH3)2 Ct CN N2
4,6-(CH3~2 H CN N2
4,6-(C~3)2 Cl COOC2H5 N2
4-CH3, 6-Cl Cl CF3 N02
4-CH3~ 6-CI F CF3 N2
4-CH3, 6-Cl H CF3 N2
4-CH3, 6-CI H N02 CF3
4-CH3, 6-CI H N02 Cl
4-CH3, 6-CI Cl Cl N2
4-CH3, 6-CI Cl CN N2
4-CH3~ 6-CI Cl COOC2H5 N02
5-CN Cl CF3 N02
5-CN F CF3 N2
5-CN H CF3 N2
5-CN H N02 CF3
5-CN H N02 Cl
5-CN Cl Cl N02
5-CN Cl CN N2
5-CN Cl COOC2H5 N2
S-CN, 6-CH3 Cl CF3 N02
5-CN, 6-CH3 F Cf3 N2
5-CN, 6-CH3 H CF3 N02
5-CN, 6-CH3 H N02 CF3
5-CN, 6-CH3 H N02 Cl
5-CN, 6-CW3 Cl Cl N2
5-CN, 6-CH3 Cl CN N2
,
,
. .
2 ~ 2 ~ ~
- 30 - O. 2 O 0050~41896
TABLE A (continuation)
X Rl R2 R3
m __ _ _ _ _
5-CN, 6-CH3 Cl COOC2H5 No2
4-CH3, 5-CN, 6-OC~Hs Cl CF3 NO2
4-CH3, 5-CN, 6~0C2H5 F CF3 NO2
4-CH3, 5-CN, 6-OC2H5 H CF3 No2
4-CH3, 5-CN, 6-OC2Hs H NO2 CF3
4-CH3, 5-CN, 6-OC2Hs H NO2 Cl
4-CH3, 5-CN, 6-OC2H5 Cl Cl No2
4-CH3, 5-CN, 6-0C2H5 Cl CN NQ2
4-CH3, 5-CN, 6-OC2H~ Cl COOC2H5 No2
4-CH(CH3)2, 5-CN, 6-0C2H5 Cl CF3 NO2
4-CH(CH3)2, 5-CN, 6-0C2Hs Cl CN No2
4-CH(CH3)2, 5-CN, 6-0C2~5 Cl COOC2H5 No2
4-CH~CH3)2, 5-CN, 6-0C2H5 Cl CONH2 No2
4-CH~CH3)2, 5-CN, 6-OC2H5 Cl COOH No2
4-CH(CH3)2, 5-CN, 6-OC2H5 F CF3 NO2
4-CH~CH3)2, 5-CN, 6-0C2H5 OC~3 CF3 NO2
4-CH(CH3)2, 5-CN, 6-0C2Hs H CF3 NO2
4-CH(CH3)2, 5-CN, 6-OC2H5 H CN NO2
4-CH(CH3)2, 5-CN, 6-OC2H5 H Cl No2
4-CH(CH3)2, 5-CN, 6-0C2H5 Cl Cl No2
4-CH~CH3)2, 5-C~, 6-OC2H5 H 502CH3 No2
4-CH(CH3)2, 5-CN, 6-0C2H5 H COOCH3 No2
4-CHICH3)2, 5-CN, 6-OC2H5 H CH3 NO2
4-CH(CH3)2, 5-CN, 6-0C2H5 H No2 CF3
4-CH(CH3)2, 5-CN, 6-OC2H~ H No2 Cl
fH3
4-CH(CH3)2, 5-CN, 6-OC2H5 H No2 CH-C2H5
4-CH(CH3)2, s-CN, 6-OC2H5 Cl Cl Cl
5-N02 Cl CF3 NO2
5-NO2 F CF3 No2
5-N02 H CF3 No2
5-N02 H NO2 CF3
5-N02 ~' N02 Cl
5-N02 Cl Cl N2
5-N02 Cl CN No2
5-N02 Cl cooC2Hs N2
6-SO~CH3 Cl CF3 NO2
6-OCH3 HCI NcOF3 CNo3
- . .
- ,. . : . :
- 2~2~
- 31 ~ O.Z. 0050/41896
TABLE A ( continuation ~
Xm Rl R2 R3
6-OCH3 H NO2 CF3
4-CH3, 5-CN, 6-OCH3 Cl CF3 NO2
4-CH3, 5-CN, 6-OCH3 H NO2 CF3
4-CH~CH3)2, 5-CN, 6-OCH3 Cl CF3 NO2
4-CH(CH3)2, 5-CN, 6-ocH3 H ~2 CF3
4-C2Hs, 5-CN, 6-OC2H5 Cl CF3 NO2
4-C2Hs, 5-CN, 6-0C2H5 H NO2 CF3
4-CH3, 6-Br Ct CF3 NO2
4-CH3, 6-Br H NO2 CF3
6-cyclo-CsHg Cl CF3 NO2
6-cyclo-C~Hg H N02 CF3
4-cyclo-C3Hs, 6-CI Cl CF3 NO2
4-cyclo-C3Hs, 6-CI H NO2 CF3
5-CN, 6-cyclo-C3Hs Ct CF3 NO2
5-CN, 6-çy~lo-C3Hs H NO2 CF3
6-OPh-4-Cl Cl CF3 NO2
6-OPh-4-CI H NO2 CF3
6-OPh-4-CH3 Cl CF3 NO2
6-OPh-4-CH3 H NO2 CF3
6-SPh-4-CH3 . Cl CF3 NO2
6-SPh-4-CH3 H NO2 CF3
S-CI,6-CH3 H CF3 No2
5-Cl,6-CH3 Cl CF3 NO2
5-Ct,6-CH3 H NO2 CF3
5-CI,6-CH3 H NO2 Cl
5 Cr,6-CH3 H CF3 No2
5-Br,6-CH3 Cl CF3 NO2
5-ar,6-CH3 H NO2 CF3
5-Br,6-CH3 H NO2 Cl
5-CI,4,6-(CH3)2 H CF3 NO2
5-CI,4,6-(CH3)2 Cl CF3 NO2
5-C1~4~6-~CH3)2 H NO2 CF3
5-C1~4~6-(CH3)2 H NO2 Cl
5 ~r,4,6-~CH3)2 H CF3 No2
5-Br,4,6-(CH3)2 Cl CF3 NO2
5-Br,4,6-~CH3)2 H NO~ CF3
5-Br,4,6-~C~3)2 H NO2 Cl
.
- . ....
. .: : .
2~3 ~$
- 3~ - O.Z. 0050/41896
TABLE B: 5-Cyanopyridine derivatives
02N Rl
NC~NH~R2 l R4 = H)
Xm R3
Xm Ri R2 R3
H Cl CF3 NO2
H C I CN NO2
H C I COOC2Hs N2
H C 1 CONH2 No2
H C I COOH NO2
H F CF3 NO2
H OCH3 CF3 NO2
H H CF3 NO2
H H CN NO2
H H Cl NO2
H Cl Cl NO2
H H SO2CH3 No2
H H COOCH3 No2
H H CH3 NO2
H H No2 CF3
U H No2 Cl
Cl H 3
H H No2 CH--C 2~1s
H Cl Cl Cl
3-CI Cl CF3 NO2
3-C I F CF3 N2
3-C I Br CF3 NO2
3-C I CF3 CF3 NO2
3-C I OCH3 CF3 NO2
3-CI OC2H5 CF3 NO2
3-C I O-n-C411g CF3 N02
3-C I OCF3 CF3 NO2
3-Ct oCf2cHF2 Cf3 N2
3-CI OC6H5 CF3 NO2
3-C I SC6H5 CF3 NO2
3-C I OC6H4 -p-C I CF3 NO2
3-CI SC6Hl,,-p-Cl CF3 N02
3-C I It CF3 N02
3-Cl H H Ct
.
` ' ., :
2 ~
- 33 - O. Z . 0050/41896
TABLE B ( continuation )
X Rl R2 R3
m
3-C 1 H Br NO2
3-Ct H Cl NO2
3-C I H CN NO2
3-C I H CONH2 No2
3-CI H CON(CH3)2 No2
3-C I H COOH N02
3-Cl H COOCH3 No2
3-Cl Cl CN NO2
3-Cl Cl COOC2H5 No2
3-C I C I CONH2 No2
3-C I C 1 COOH NO2
3-CI H 52CH3 No2
3-C I H 52NH2 NO2
3-CI H So2N(cH3)2 No2
3-C I H CH3 No2
3-C I H C ( CH3 ~ 3 No2
3-C I H OCF3 No2
3-Cl H OCF2CHF2 No2
:3-CI H NO2 CF3
3-Cl H NO2 Cl
3-Cl ~ N02 CH3
fH3
3-Cl H N02 CH--C 2t1s
3-Cl Cl Cl NO2
3-CI Cl Cl Cl
3-CI H CF3 H
3-Cl Cl H H
3-N02 Cl CF3 NO2
3-N(~2 F CF3 N2
3-N02 H CF3 No2
3-N02 H NO2 Cf 3
33-NNOo22 HCI Ncl2 NO2
3--N02 Cl CN No2
3-N02 Cl COOC2H5 No2
3-Cr Cl CF3 ~2
3-Br Cl CN NO2
3-Br Cl COOC~H5 No2
3-Br Cl CONW2 NO2
~13~2~
- 34 - O . Z O 0050/41896
TABLE B ( cor~tinuation )
x Rl R2 R3
m _ __ _ _ _ _ _ .
3-~r F CF3 NO2
3-Br OCH3 CF3 N~2
3-Br H CF3 No2
3-Br H CN NO2
3-~r H Cl NO2
3-Br Cl Cl ~2
3-Br H SO2CH3 No2
3-Br H COOCH3 No2
3-Br H CH3 NO2
3-Br H NO2 CF3
3-Br H NO2 Cl
CH3
3-Br H NO2 CH-C2Hg
3-Br Cl Cl Cl
33-CF~ Cf~ CF3 N02
3-CF3 H CF3 No2
3-CF3 H NO2 CF3
3-CF3 ~ NO2 Cl
3-CF3 Cl Cl No2
33-CCF33 ccl cooC2H5 NNo22
4,6-(CH3)2 F rFF3 NNcoo22
C~3~2 ~ 1 n~
6-Cl H NO2 CF3
~,~ C12 ~ 2H5
,
2 ~1 ~
- 35 - O. Z . 0050/41896
T~BLE B (continuation)
Xm Rl R2 R3
3,6-C12 ~I CF3 NO2
3,6-C12 H N02 CF3
3,6-C12 H N02 Cl
3 6-C12 Cl Cl No2
3,6-CI~ Cl CN N02
3 6-C12 Cl COOC2H5 No2
4-CH3 Cl CF3 N02
4-CH3 H N02 CF3
6-CH3 Cl CF3 N02
6-CH3 H N02 CF3
3-CI, 6-OC2H~ Cl CF3 N02
3-Cl, 6-OC2H5 H N02 CF3
3-CI, 6-OC6Hs Cl CF3 N02
3-Cl, 6-OC6Hs H N02 CF3
3-CI, 6-502C~3 Cl CF3 N02
3-CI, 6-S02CH3 H N02 CF3
3-Cl, 6-CH3 H CF3 No2
3-CI, 6-CH3 Cl CF3 N02
3-CI, 6-CH3 H N02 CF3
3-Cl, 6-CH3 H N02 Cl
3-Br, 6-CH3 H CF3 N02
3-Br, 6-CH3 Cl CF3 No2
3-Br, 6-CH3 H N02 CF3
3-Br, 6-CH3 H N02 Cl
3-CI, 4,6-(CH3)2 H CF3 No2
3-CI; 4,6-~CH3)2 Cl CF3 N02
3-Cl, 4,6-(CH3)2 H N02 CF3
3-CI, 4,6-(CH3)2 H N02 Cl
3-Br, 4,6-(CH3)2 H CF3 No2
3-Br, 4~6-(cH3)2 Ct CF3 No2
3-Br, 4,6-~CH3)2 H W02 CF3
3--~r, 4,6-(CH3)2 H N02 Cl
~;:
, ~ .
2~2~
- 36 - O.~. 0050/41~96
TABL~ C:
CN 2N Rl
5 ~ NR4 ~ R2
Xm
Xm/CN Rl R2 R3 R4
-- : ,
3-CN Cl CF3 NO2 SO2C6H5
3-CN Cl CF3 NO2 CH2-CH=CH2
3-CN Cl CF3 NO2 CH2-C--CH
3-CN H NO2 CF3 CQCH2CI
5-CN Cl Cf3 NO2 SO2C6H5
5-CN Cl CF3 NO2 CONH2
5-CN H NO~ CF3 COOCH2C6H5
5-CN H NO2 CF3 SO2C6~5
3-Cl, 5-CN H H Cl 5O2C6H5
3-CI, 5-CN Ci CF3 NO2 CH2-CH=C~2
3-CI, 5-CN Cl CF3 NO2 CH2-C_CH
3-CI, 5-CN H CF3 H SO2C6H5
3-CI, 5-CN Cl CF3 NO2 SO2C6H5
3-CI, 5-CN Cl CF3 NO2 COCH3
3 Cl, 5-CN Cl CF3 NO2 COCHC12
3-CI, S-CN Cl ~F3 NO2 CC6~5
3-CI, 5-CN Cl CF3 NO2 COOCH3
3-CI, 5-CN Cl CF3 NO2 CONH2
3-Cl, S-CN Cl CF3 NQ2 CHO
3-CI, 5-CN H NO2 CF3 SO2c6~15
3-CI, 5-CN H NO2 CF3 COOCH3
3-Cl, 5-CN H NO2 CF3 COCH2CI
6-CI, 3-CN Cl CF3 ~2 SO2C6H5
6-C!, 3-CN H NO2 CF3 5O2C6H5
6-CI, 5-CN Cl CF3 NO2 SO2C6H5
6-CI, 5-CN H NO2 CF3 SO2C6H5
4-CU(CH3)2, 6-0C2H5~ 3~5-(CN)2 Cl CF3 NO2 SO2C6H5
4-CH(CH3)2, 6-OC2H5, 3~5-(CN~2 H NO2 CF3 SO2C6H5
5-CI, 3-CN Gl CF3 NO2 5O2C6Hs
5-CI, 3-CN Cl CF3 NO2 COOCH3
5-Cl, 3-CW Cl CF3 NO2 COrlH2
5-CI, 3~CN Cl CF3 NO2 COC6H5
':
:: :
2 ~ 8
- 37 - O. Z . 0050/~1896
TABLE C: ( continuation )
Xm/CN R1 R2 R3 R4
, _
5-CI, 3-CN H NO2 CF3 502C6H5
5-CI, 3-CN H NO2 CF3 COOCH3
5-CI, 3-CN H NO2 CF3 CONH2
5-CI, 3-CN H NO2 CF3 COC6H5
5-CI, 3-CN H NO2 CF3 COcHc12
6-cyclo-C3Hs, 3-CN Cl CF3 NO2 502C6H5
6-CH3, 3,5-(CN12 Cl CF3 NO2 SO2C6~l5
6-CH3, 3,5-(CN~2 H NO2 CF3 SO2C6~l5
6-C1, 4-CN Cl CF3 NO2 SO2C6H5
6-CI, 4-CN H NO2 CF3 SO2C6H5
4,6-tCH3)2~ 3-CN Cl CF3 NO2 502C6H5
4,6-(CH3~2~ 3-CN H NO2 CF3 SO2C6~5
4,6-fCH3)z, 3-CN H CH3 No2 SO2C6H5
'
: ' ' ~' '
`: :
~ 1 2 ~ ~
- 38 - O.Z. 0050/41896
TABLE D
CN 2N Rl
m .
~m/CN Rl R2 R3 M+
3-CN Cl CF3 N02 K+
3-CN Cl CF3 N02 N(CH3~4
3-CN Cl CF3 N02 N~C4H9)4~
3-CN Cl CF3 N02 C6H5-NH(CH3)2
3-CN Cl CF3 N02 NHtC2H5)3
3-CN H N02 CF3 K+
3-CN H N02 CF3 N(CH3)4
3-CN H N02 CF3 N(C4H9)4
5-CN Cl CF3 N02 K+
5-CN Cl CF3 N02 N~c4Hg)4
5-CN H N2 CF3 N(c4Hg)4
3-CI, 5-CN Ct CF3 N02 K+
3-CI, 5-CN Cl CF3 N02 N5CH3)4
3-CI, 5-CN Cl CF3 N02 N(C4H9)4+
3-CI, 5-CN Cl CF3 ~2 NH2(i-c3~17)2
3-CI, 5-CN Cl CF3 N02 (cH3)3NcH2cH2oH+
3-CI, 5-CN H N02 CF3 K+
3-CI, 5-CN H N02 CF3 N(C4Hg)4
3-Cl, 5-CN H N2 Cf3 NH2(i-C3~7)2
3-Br, 5-CN Cl CF3 N02 : N(c4H9)4
3-arj 5-CN H N02 c~3 N(C4H9)4
5-CI, 3-CN Cl CF3 N02 K+
5-CI, 3-CN Ct CF3 N2 N(C4H9)4
5-CI, 3-CN H N2 CF3 K+
5-CI, 3-CN H N2 CF3 N(c4H9)4+
5-~r, 3-CN Cl CF3 N02 N~C4Hg)~t
5-8r, 3-CN H N02 CF3 N(C4H9)4
6-CI, 3-CN Cl CF3 N02 N(c4M9)4
6-CI, 3-CN H N02 CF3 N~C4H9)4
..
: . ~ , .
2 ~ ~
39 - O . Z . 0050~ 896
TA13LE D ( continuation )
Xm/CN R1 R2 R3 M+
4-CH(CH3)2, 6-OC2H5~ Cl CF3 N02 N(C4H9)4
3,5-(CN)2
4-CH(CH3)2, 6-0C2H5~ H N02 tF3 N~C4H9)4
3,5_(CN)2
6-CH3, 3,5-(CN)2 Cl CF3 N02 N(C4H9)4
6-CH3, 3-CN Cl CF3 N02 N(C4H9)4
6-cyclo-C3H5, 3-CN Cl CF3 N02 N(C4~9)4
6-CI, 4-CN Cl CF3 N02 N(C4H9)4
6-CI, 4-CN H N02 CF3 N(C4H9)4
4~6-(CH3)2~ 3-CN Cl ~F3 N02 N(C4~9)4
4,6-(CH3)2, 3 CN H N02 CF3 N(C4H9)4
4~6-(CH3)2~ 3-CN H CH3 N2 N(C4Hg)4t
6-C~(CH3)2, 3-CN Cl CF3 N02 N(C4H9)4
3-CN,5-Cl,4,6-(CH3)2 H N02 CF3 K~
3-CN,5-Cl,4,6-(CH3)2 H N02 Cl K+
3-CN,5-8r,4,6-(CH3)2 H N02 CF3
3-CN,5-Br,4,6-(CH3)2 H N02 Cl K~
5-CN,3-CI,4,6-(CH3)2 H N02 CF3 K~
5-CN,3-CI,4,6-(CH3)2 H N02 Cl K+
5-CN,3-Br,4,6-(CH3)2 ~ N02 CF3 K~
5-CN,3-Br,4,6-(CH3)2 H N02 Cl K~
3-CN,5-CI,4,6-(CH3)2 H N02 Cf3 N(CH3)4
3-CN,5-CI,4,6-(CH3)2 H N02 Cl N(CH3)4
3-CN,5-Br,4,6-(CH3)2 H N~2 CF3 N(CH3)4
3-cN~5-Br~4~6-(cH3)2 H N02 Cl N(CH3)4
5-CN,3-CI,4,6-(CH3)2 H N02 CF3 N(CH3)4
5-CN,3-Cl,4,6-~CH3)2 H N02 Cl N(CH3)4
5-cN~3-Br~4~6-(cH3)2 H N02 CF3 N(CH3)4
5-CN,3-Br,4,6-(CH3)2 H N02 Cl N(CH3)~
3-CN,5-CI,4,6-(CH3)2 H N02 CF3 N(n-C4Hg)4
3-CN,5-CI,4,6-~cH3)2 H N02 Cl N(n-c4H9)4
3-CN,5-Br,4,6-~CH3)2 H N02 CF3 N(n-C4Hg)4
3-CN,5-Br,4,6-(CH3)2 ~ N02 Cl N(n-C4Hg)4
5-CN,3-CI,4,6-(CH3)2 H. N2 CF3 N(n-C4Hg)4
5-CN,3-CI,4,6-(CH3)2 H N02 Cl N(n-C4Hg)4
5-CN,3-Br,4,6-(CH3)2 H N02 CF3 N(n-C4Hg)4
5-CN,3-Bn,4,6-(CH3)2 H ~12 Cl N(n-C4Hg)4
.::. , :
:.
: . . :
- 40 - O.Z. 0050/41896
TABLE D (continuation)
Xm/ _ _ Rl R2 R3 M+ _
3-CN,5-Cl,4,6-(CH3)2 H N02 CF3 (i-c3H7)2N~c2~5
3-CN,5-CI,4,6-(CH3)2 H N02 Cl (i-c3H7)2NHc2H5
3-CN,5-Br,4,6-(C~3)2 ~ N02 CF3 (i-C3H7)2NHC2H5
3-CN,5-Br,4,6-(CH3)2 H N02 Cl (i-C3H7)2N~C2HS
5-CN 3-C1,4,6-(CH3)2 H N02 CF3 (i~C3H7)2NHC2H5
5-CN 3-C1,4,6-(CH3)2 H N02 Cl (i-c3H7)2~Hc2Hs
5-CN,3-Br,4,6-(CH3)2 H N02 CF3 (i-C3H7)2NHC2H5
5-CN,3-Br 4,6-(C~I3)2 H N02 Cl (i-C3H7)2NHC2HS
3-CN,S-CI 4~6-(cH3)2 H NQ2 CF3 C6HsCH2N(~H3)3
3-CN,S-cl~4~6-(cH3)2 H N02 Cl C6H6CHzN(CH3)3
3-CN,5-Br,4,6-(CH3)2 H N02 CF3 C6H6CH2N(CH3)3
3-CN,5-~r,4,6-(CH3)2 H N02 Cl C6H6CH2N(CH3)3
5-CN,3-CI,4,6-(cH3)2 H N2 CF3 C6H6CH2N~CH3)3
5-CN,3-C1,4,6-(CH332 H NOz Cl C6H6CH2N(CH3)3
5-CN 3-Br,4,6-(CH3)2 H N02 CF3 C6H6CH2N(CH3)3
S-CN 3-Br,4,6-(CH3)2 H N02 Cl C6H6CH2N(CH3)3~
The compounds of th~ ~ormula I are suitable for
effective control of pests from the classes of insects,
arachnids and nema~odes. They can be employed as pesti-
cides in crQp protection and in the hygiene, store-
protection and ~eterinary ~ectors.
The in~ect pests include those from the order of
Lepidoptera, for example Agroti~ ypsilon, Agrotis
seg0tum, ~labama aryillacea, Anticarsia gemmatali~,
Argyresthia con~ugella, Autographa gamma, Bupalus
piniarius, Cacoecia murinana, Capua reticulana,
Cheimatobia brumata, Choristoneura fumifexana,
Chori~toneura occidentali~, Cirphis unipuncta, Cydia
pomonelLa, Dendrolimu~ pini, Diaphania nitidalis,
Diatraea grandiosella, Earia~ insulana, Ela~mopalpus
ligno~ellu~, Eupoecilia ambiguella, Evetria bouliana,
Feltia ~ubterranea, Galleria mellonella, Grapholita
funebrana~ Grapholita molesta, Heliothis armigera,
2 ~ ~
41 - O.Z. 0050/~1896
Heliothis virescens, Heliothis zea, Hellula undalis,
Hibernia defoliaria, Hyphantria cunea, ~Iyponomeuta
malinellus, Keifferia lycopersicella, Lambdina
fiscellaria, Laphygma exigua, Leucoptera cofeella,
Leucoptera scitella, Lithocolletis blancardella, Lobesia
botrana, Loxostege sticticalis, Lymantria dispar,
Lymantria monacha, Lyonetia clerkella, Malacosoma
neustria, Mamestra brassicae, Orgyia psPudotsugata,
Ostrinia nubilalis, Panolis flameaJ Pectinophora
gossypiella, Peridroma saucia, Phalera bucephala,
PhthorLmaea operculella, Phyllocnistis ci~rella, Pieris
bras~icaa, Plathypena scarbra, Plutella ~ylostella,
Pseudoplusia includens, Phyacionia frustrana,
Scrobipalpula absoluta, Sitotroga cerelella, Sparganothis
pilleriana, Spodoptera frugiperda, Spodoptera littoralis,
Spodoptera litura, Thaumatopoea pityocampa, Tortrix
viridana, Trichoplusia ni, Zeiraphera canadensis.
From ~he order of Coleoptera, for example Agrilus
sinua~us, Agriotes lineatus, Agriotes obscurus,
AmphLmallus solstitialis, Anisandrus dispar, Anthonomus
grandis, Anthonomus pomorum, Atomaria linearis,
Blastophagus piniperda, Blitophaga undata, Bruchus
rufimanus, Bruchus pisorum,. Bruchus lentis~ Byctiscus
hetulae, Cas~ida nebulosa, Cerotoma trifurcata,
Ceuthorrhynchu3 assimili~, Ceuthorrynchus napi,
Chaetocnema tibialis, Conoderus vespertinus, Crioceris
a~paragi, Diabrotica longicornis, Diabrotica 12-punctata,
Diabro~ica virgifera, Epilachna varivestis, Epitrix
hirtipenni~, Eutinobothrus brasiliensis, Hylobius
abieti~, ~ypera brunneipennis, H~pera postica, Ip5
typographus, Lema bilineata, Lema melanopus, Leptinotarsa
decemlineata, Limoniu~ californicu~, Lis~orhoptrus
ory~ophilu~, Melanotus communis, Meligethes aeneus,
Melolontha hippocastani, ~elolontha melolontha, Onlema
oryza~, Ortiorrhynchu~ sulcatus, Otiorrhynchus ovatus,
Phaedon cochleariae, Phyllotreta chrysocephala,
Phyllophaga sp., Phyllopartha horticola, Phyllotrata
2~2~ -
- ~2 - O.Z. 0050/~1896
nemorum, Phyllotreta striolata, Popillia japonica, Sitona
lineatus, Sitophilus granaria.
From the order of Diptera, for example Aedes
aegypti/ Aedes vexans, Anastrepha ludens, Anopheles
maculipenni~, CPratitis capitata, Chrysomya be~ziana,
Chrysomya hominivorax, Chrysomya macellaria, Contarinia
sorghicola, Cordylobia anthropophaga, Culex pipiens,
Dacus cucurbitae, Dacus oleae, Vasineura brassicae,
Fannia canicularis, Gasterophilus intestinalis, Glossia
morsitans, Haematobia irritans, Haplodiplosis equestris,
Hylemyia platura, Hypoderma lineata, Liriomy~a sativae,
Liriomyza trifolii, Lucilia caprina, I.ucilia cuprina,
Lucilia sericata, Lycoria pectorali , Mayetiola
destructor, Musca domestica, Muscina stabulans, Oestrus
ovis, Oscinella frik, Pegom~a hyoscyami, Phorbia anti~la,
Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi,
Rhagoletis pomonella, Tabanus bovinus, Tipula oleracea,
Tipula paludosa.
Yrom the order of Thysanoptera, for example
Frankliniella fu~ca, Frankliniella occidental:is,
Frankliniella tritici, Scirtothrips citri~ Thrips oryzae,
Thrips palmi, Thrips tabaci.
From the order of Hymenoptera, for example
Athalia rosae, Atta cephalotes, Atta sexdens, Atta
texana, Hoploc~mpa minuta, Hoplocampa testudinea,
Monomorium pharaonis, Solenopsis geminata, Solenopsis
invicta .
From the order of Heteroptera, for example
Acrosternum hilare, Blissu~ leucopterus, Cyrtopeltis
~otatu~, Dysdercu~ cingulatus, Dysdercu~ intermedius,
Eu~ygaster integriceps, Euchistus impictiventris,
Leptoglossus phyllopus, Lygus lineolaris, Lygus
praten~is, Nezara viridula, Pie~ma quadrata, Solubea
in~ularis, Thyanta perdi~or.
From the order of Homopters, for example
~cyrthosiphon onobrychis, Adelges laricis, ~phidula
nastur~ii, Aphis fabae, Aphis pomi, Aphi~ sambuci,
2 ~
- 43 - O.Z. 0050/41896
Brachycaudus cardui, Brevicoryne brassicae, Caro~ipha
gossypii, Dreyfusia nor~mannianae, Dreyfusia piceae,
Dyasphis radicola, Dysaulacorthum pseudosolani, Empoasca
fabae, Macrosiphum avenae, Macrosiphum euphorbiae,
Macrosiphen rosae, Megoura viciae, Metopolophium
dirhodum, Myzodes persicae, Myzus cerasi, Nilaparvata
lugens, Pemphigus bursarius, Perkinsiella saccharicida,
Phorodon humuli, Psylla mali, Psylla piri, Rhopalomyzus
ascalonicus, Rhopalosiphum maidis, Sappaphis mala,
Sappaphis mali, Schizaphis graminum, Schizoneura
lanuginosal Trialeurode~ vaporariorum, Viteus vitifolii.
From the order of Isoptexa, for example
Calotermes flavicollis, Leucotermes fl vipes,
Reticulitermes lucifugus, Termes natalensis.
From the order of Orthoptera, for example Acheta
domestica, Blatta orien~alis, Blat~ella germanica,
Forficula auricularia, Gryllotalpa gryllotalpa, Locusta
migratoria, Melanoplus birittatus, Melanoplu~ femur-
rubrum, Melanoplus mexicanus, Melanoplus sanguinipes,
Melanoplu~ spretus, Nomadacris septemfasciata,
Periplaneta americana, Schistocerca americana,
Schistocerca peregrina, Stauronotus maroccanus,
Tachycine~ asynamoru~.
From the cla~ o ~rachnoidea, for example
arachnids (Acarina) such as Amblyomma americanum,
Amblyomma variegatumr Argas persicus, Boophilus
annulatua, Boophilu~ decoloratu~, Boophilu~ microplu~,
Brevipalpu~ phoanicis, Bryobia praetiosa, Dermacentor
silvarum, Eo~e~ranychus carpini, Eriophya~ sheldoni,
~Iyalomma truncatum, Ixodes ricinus, Ixode~ rubicundus,
Ornithodorus moubata, Otobins megnini, Paratetranychus
pilo~u~, Permanyssu~ gallinae, Phyllocap~rata oleivora,
Polyphagotarsonemu3 latus, P~oropte3 ovis, Rhipicephalus
appendiculatus, Rhipicephalus evertsi, Saccoptes scabiei,
Tetranychus cinnabarinu~, Tetranychus kanzawai,
Tetranychu~ pacificu~, Tetranychus telarius, Te-tranychu~
urticae.
2~2~$
- 44 - O.Z. 0050/41896
From the class of nematode~, for example root
knot nematodes, eg. Meloidogyne hapla, Meloidogyne
incognita, Meloidogyne javanica, cyst-forming nematodes,
eg. Globodera rostochiensis, Heterodera avenae,
Heterodera glycinae, Heterodera schatii, Heterodera
triflolii, stem and leaf eel~orms, eg. Belonolaimus
longicaudatus, Ditylenchus destructor, Ditylenchus
dipsaci, Heliocotylenchus multicinctus, Longidorus
elongatus, Radopholus similis r Rotylenchus robustu~,
Trichodorus pximitivus, Tylenchorhynchus claytoni,
Tylenchorhynchus dubius, Pratylenchus neglec~us,
Pratylenchus penetrans, Pratylenchus curvitatus~
Pratylenchus goodeyi.
The active ingredients may be applied a~ such or
in the form of theîr formulation~ or of the application
forms prepared therefrom, eg. in the form of directly
sprayable solutions, powders, suspension~ or dispersions,
emulsions, oil dispersions, p~stes, dusting or broadcast-
ing agen~s, or granules by spraying, atomizing, dusting,
broadca~ting or watering. ~he application form~ depend
entirely on the purposes for which they are used; they
should in every case ensue the finest pos~ible distribu-
tion of th~ active ingredients according to the
invention.
Suitable for preparing directly sprayable solu-
tion~, emulsion~, pastes or oil disperxions are mineral
oil fractions of medium to high boiling point such as
kerosene or diesel oil, also coal~ar oils and oils of
vega~able or animal origin, aliphatic~ cycllc and aro-
matic hydrocarbons, eg. benzene, toluene, xylene, paraf-
fin, tetrahydronaphthalene, alkylated naphthalenes or
derivative~ thereo, methanol, ethanol, propanol, buta-
nol, chloroform, tetrachloromethan~, cyclohexanol,
cyclohexanone, chlorobenzene, isophorona, highly polar
solvents, eg. dimethylformamider dimethyl sul~o~ide,
N-methylpyrrolidone or wate.r.
Aqueou~ application forms can b~ prepared from
'
2~ 2~
- 45 - O.Z. 0050/41896
emulsion concentrates, pastes or wettahle powders (oil
dispersion~) by adding water. To prepare emulsions,
pastes or oil dispersions, the substances can be homogen-
ized, as such or dissolved in an oil or solvent, in water
using ~he we~ting agents, adhesion promoters, dispersants
or emulsifiers. However, it is also possible to prepare
concentrates which are composed of active substance,
wetting agent, adhesion promoker, dispersant or emulsi-
fier and, possibly, solvent or oil and which are suitable
for dilution with water.
Suitable surfactants are alkali metal, alkaline
earth metal or ammonium salts o lignin~ulfonic acid,
naphthalenesulfonic acid, phenolsulfonic acid, dibutyl-
naph~halene~ulfonic acid, alkylarylsulfonates, alkyl
sulfates, alkylsulfonates, fatty alcohol sulfates and
fatty acids and the alkali metal and alkaline earth metal
salts thereof, salts of sulfated fatty alcohol glycoL
ethers~ products of the condensation of sulfonated
naphthalene and naphthalene derivatives with ormalde-
hyde, products of the condensation of naphthalene or
naphthalene~ulonic acid with phenol and formaldehyde,
polyoxyethylene octylphenol ether, ethoxylated isooctyl-
phenol, octylphenol, nonylphenol, alkylphenol polyglycol
ethers, tributylphenyl polyglycol athers, alkylaryl
polyether alcohols, isotridecyl alcohol, fatty alcohol/
ethylene oxide condensates, etho~ylated castor oil,
polyoxyethylen3 alkyl ether~, etho~ylated polyoxypropyl-
ene, lauryl alcohol polyglycol ether acetal, sorbitol
ester~, lignin~ulide waste liquors and methylcellulose.
Powders and dusting and broadcasting agents can
be prepared by mixing or gxindiny the active substances
together with a ~olid carrier.
The formulations generally contain from 0.01 to
95 % by weight, preferably from 0.1 to 90 % by weight of
the active ingredient. The active ingredient~ axe em-
ployed in a purity o~ rom 90 to 100 %, preferably 95 to
100 % (according to tha NMR spectr~m3.
:
2~1,?'~8
- 46 - O.Z. 0050/41896
Examples of formulations are gi~en below~
I. 5 parts by weight of compound No. 1.001 are inti-
mately mixed with 95 parts by weight of finely
divided kaolin. ~his results in a dusting agent
S which contains 5 % by weight of active
ingredient.
II. 30 parts by weight of compound No. 1.027 are
intimately mixed with a mixture of 92 part~ by
weight of powdered silica gel and 8 parts by
weight of liquid paraffin which has been sprayed
onto the surface o this gel. ~his formulation of
~he active ingredient adheres well (content of
active ingredient 23 % by weight).
III. 10 parts by weight of compound No. 1.037 are dis
solved in a mixture compo~ed of 90 part~ by
weight of xylene, 6 parts by weight o the adduct
of 8 to 10 moles of ethylene oxide and 1 mole of
oleic acid N-monoethanolamide, 2 p~rt~ by weight
of calcium dodecylbenzenesul~onate and 2 parts by
weight of the adduc~ of 40 moles o~ e~hylene
oxide and 1 mole of castor oil (content of active
ingredient 9 % by weight).
IV. 20 part3 by weight of compound No. 2.009 are dis-
solved in a mixture compo~ed of 60 parts by
weight of cyclohexanone, 30 part~ by weight of
isobutanol, S parts by weight of the adduct of
- 7 mole~ o~ ethylene oxide and 1 mole of isooctyl-
phen~l and 5 parts by weight of the adduct of
40 mole~ of ethylene oxide and 1 mole of ca~tor
oil (content of active ingredient 16 % by
weight).
V. 80 parts by weight of compound No. 2.021 are
thoroughly mixed with 3 parts by weight o~ ~odium
diisobutylnaphthalene-alpha-sulfonate, 10 paxts
by weight of khe sodium salt of a ligninsul~onic
acid from a ~ulfite wastQ liquor and 7 part~ by
welght of powdered silica gel and ground in a
: ~ ' ,~ ''
., ~ :
2 ~ 3
- 47 - O.~. 0050/41896
hammer mill (content of active ingredient 80 % by
weight).
VI. gO par~s by weight of compound No. 3.001 are
mixed with 10 parts by weight of N-methyl-~-
pyrrolidone to give a solution which is suitable
for application in the form of very fine drops
(content of active ingredient 90 % by weight).
VIIo 20 parts by weight of compound No. 4.002 are dis-
sol~ed in a mixture composed of 40 parts by
weight of cyclohexanone, 30 parts by weight of
isobutanol, 20 parts by weight of the adduct of
7 moles of ethylene oxide and 1 mole of isooctyl-
phenol and lO parts by weight of the adduct of
40 moles of ethylene o~ide and 1 mole of cast:or
oil. A f.ine dispersion of the solution in
100 000 pa~ts by weight of watex contains 0.02 %
by weight of active ingredient.
VII~. 20 parts by w~ight of active ingredient No. 4.tlO9
are thoroughly mixed with 3 parts by weight of
sodium diisobutylnaphthalene-~-sulfonate,
17 parts by weight of the sodium salt of a
ligninsulfonic acid from a sulfite waste liquor
and 60 parts by waight of powdered ~ilica gel and
ground in a hammer mill. A fine dispersion of the
mixture in 20 000 parts by weight of water
contains 0.1 % by weight of active ingredient and
can be used for spraying.
Granules, eg. coated, impregnated or homogeneous
granule~, can be prepared by binding the active ingredi~
ent~ to solid carriers. Examples of solid carriers are
mineral earth~ such as 3ilica gel, 5ilicic acids, sili-
cate~, talc, kaolin, attapulgite, limestone, lime, chalk,
bole, loess, clay, dolomite, diatomaceous earthr calcium
and magnes.ium sulfate, magnesium oxide, ground plastics,
~ertilizer such as, for example, ammonium sulfate,
ammonium phosphate, ammoni.um nitrata, ureas and vegetable
products such a~ cereals flour, bark meal, wood meal and
- : .
,
~. , , .~ .
2 ~
- 48 - O.Z. 0050/41896
nutshell meal, cellulose powder and other solid carriers.
The concentrations of the active ingredients in
the formulations ready for application can vary within
wide lLmits.
5They are generally from 0.0001 to 10 ~, prefer-
ably from 0.01 to 1 %.
The active ingredients can also be used success-
fully in the ultra low volume (ULV) process, in which
case it is possible to apply formulations containing more
10than 95 % by weight of active ingredient or even the pure
active ingredient.
The application rate of active ingredient in the
open is from 0.01 to 3 kg/ha, preferably 0.1 to 2 kg/ha
active substance.
15~h~ active ingredients can be mix2d with oils of
~arious types, herbicides, fungicides, other pesticides,
bactericides, where appropriate ~ust before application
(tank mix). The~e agents can be mixed ~ith the agents
according to the invention in the ratio of from l:10 to
2010:1 by weight.
S~NTHESIS EXA~?hES
The proce3ses described in the following syn-
thesis examples were used, with appropria~e modification
of the starting ~ompounds, to obtain other Compounds I.
25The compounds obtained in this way are listed with
physical data in the tables which follow.
EXAMP~E 1
A solution of 5.6 g (0.051 mol) of potassium
tert-butylate in 50 ml of tert-butanol is added dropwi~e
30over the course of 1 h to a vigorou~ly stirred suspension
of 5.6S g (O.025 mol) of 2-amino-5-bromo-3-cyano-4,6-
dimethylpyridine and 7.4 g (0.0275 mol) of 2,4-dinitro-
6-trifluoromethylchlorobenzene in 60 ml of 1:1 tetra-
hydrofuran/tert~butanol at 0 - 5~C. After 1 h at 0C, the
35mixture i~ warmed to room temperature (20C) over the
course of 2 h and then acidified (pH 4) with glacial
acetic acid, diluted with 0.2 1 of water and extracted
. .
2~2~
- 49 - O.Z. OOsO/41896
3 times with 50 ml of diethyl ether each time. The
combined ether extracts are washed with saturated NaCl
solution, dried over MgS04 and concentrated, and the
residue is stirred with ethanol; 10.9 g (9S % of theory)
of Compound 1.034 are obtained as yellow crystals of
melting point 147-149C.
EXAMPL~ 2
0.24 g (0.01 mol) of sodium hydride is added a
little at a tLme to a solution of 3.4 g (O.01 mol) of 3-
chloro-5-cyano-2-(2-nitro-4-trifluoromethylanilino)pyri-
dine (Compound 2.016) in 25 ml of tetrahydrofuran. After
15 min., 3.5 g (0.02 mol) of benzenesulfonyl chloride are
added dropwi~e at room temperature. After 48 h at 60C,
150 ml of wa~er are added and the mixture is extracted
3 tLme~ with 100 ml of ether each time. The combined
ether extracts are wa~hed with saturated NaCl solution,
dried over MgS04 and concentr~ted. The residue i~ ohro
matographed (silica gel, cyclohexane/ethyl acetate 9:1).
1.5 g (31 % of theory) of Compound 3.001 are obtained as
yellow crystals of meltiny point 147-158C.
:.
- . ~ ,
2~ ~ 2~
50 - O.Z. OO50f41896
TABLE 1
CN O2N ~1
NH ~ R2 I R4 = H)
Xm
No. XmRl R2 R3 melting point
. . . _ _ . . " " " ", _ _
1.001 H Cl CF3 N02 157-158
1.002 H H No2 CF3 112-115
1.003 5-Cl Cl CF3 N02 155-156
1.004 5-Cl H CF3 ~2 167-168
1.005 5-CI Cl co2c2Hs No2 216-220
1.006 5-CI H NO2 CF3 153-155
1.007 S-Ct H N02 Cl 212-213
1.008 5-Br Cl CF3 NOz 136-138
1.009 5--~r H NO2 CF3 154-156
1.010 6-CI Cl CF3 NO2 130-134
1.011 6-Cl H NQ2 CF3 156-159
1.012 6-c-C3H7 Cl CF3 NO2 160
1~013 6-C-c3H7 H CF3 No2 168~171
1.014 6-c-C3H7 H N02 CF3 169-173
1.015 6-;-C3H7 Cl CF3 NO2 138-141
1.016 6-;-C3H7 H CF3 NO2 136
1.017 6-i-C3~7 H NOz CF3 125-131
1.018 6-CH3 Cl CF3 NO2 163
1.019 6-CH3 H CF3 No2 204-206
1.020 6-CH3 H NO2 C~3 131-132
1.021 4,6-CH3 Cl CF3 NO2 155
1.022 4,6-CH3 H CF3 No2 215-216
1.023 4,6-CH3 ~i N02 CF3 145-152
1.024 4,6-CH3 H C(CH3~3 No2 192-194
1.025 4,6-CH3 H CN No2 203 (decomposition3
1.026 4-CH3,6-Cl Cl CF3 N02 148-158
1.027 4-CH3,6-CI H NO2 CF3 128-133
1.028 5-CN,6-CH3 Cl CF3 Na2 > 220
1.029 5-CN,6-CH3 H NO2 CF3 12S
1.030 4-CH3,5-CN, Cl CF3 NO2 120
6-OC2~5
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- 51 - O. Z . 0050/41896
TABLE 1 (continuakion)
No . Xm Rl R2 R3 melting point
.
1.031 4-CH3, 5-CN, H N02 CF3 > 220
6-OC2~5
1.032 4-CH(CH3)3, Cl CF3 N02 165-167
5-CN, 6-OC2Hs
1.033 4-CH(CH3)3~ Cl C02C2Hs No2 173-174
5-CN,6-OC2Hs
1.034 5-Br,4,6- H N02 CF3 147-14
-(CH3)2
1.035 5-Br,4,6- Cl CF3 No2 181-183
-(CH3)2
1.036 4-CH~CH3)2, H NO2 CF3 183-185
S-CN,
6-OC2Hs
1,037 4-CH(CH3)2t H NO2 Cl 219-221
5-CN,
6-OC2H5
.
52 - O. Z . 005Q/41~96
TABLE 2
02N Rl
NC~NH~R 2 1 ( R 4 = H )
Xm
No. Rl R2 R3 m-p. ( C)
2.001 H Cl CF3 NO2 159-161
2.002 H H No2 Cf3 141-144
2.003 3-CI C1 CF3 NQ2 173-175
2.004 3-CI F CF3 No2 133-136
2.005 3-CI H CF3 N02 134-135
2.005 3-CI H CN N02 210-212
2.007 3-CI H C02CH3 No2 185-187
2.008 3-CI Cl C02C2H5 No2 182-188
2 009 3-CI H 502CH3 No2 >220
2 010 3-CI H CH3 No2 155
2.011 3-CI H C~CH3)3 No2 175-178
2 012 3-CI H N02 CF3 117-119
2 013 3-CI H N02 Cl 135-138
2 015 3-CI H NCCOIZ CH(CH3)C2~5 13 ~33
2 017 3-Br H NO2 CF3 124-126
2 018 4,6-(CH3)2 Cl CF3 No2 >220
2 019 6-CI Cl CF3 NO2 203-204
2 020 6-CI H N02 CF3 176-185
2.021 3-Br Cl CF3 N02 151-155
2.022 3-Br~4,~-(CH3)2 Cl CF3 N02 173-175
2.023 3-~r~4~6-(cH3)2 H NO2 CF3 131-135
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- 53 ~ O.Z~ OOS0/41896
TABLE 3:
CN O2N Rl
s ~ ~ N-R4 ~ R2
Xm
No. Rl R2 R3 R4 m.p. ( C)
3.Q01 3-Cl,5-CN H CF3 H 52C6Hs 147-158
TABLE 4.
CN o2N R
~R 2 Me~
m
Xm/CN Rl R2 R3 M3 m.p. (~C)
4.001 3-CI,5-CN Cl CF3 NO2 K~ 175
4.002 3-Cl,5-CN C1 CF3 N02 N(CH3)4~ 198
4.003 3-CI,5-Cn Cl CF3 No2 N¦n-C4H9)4~110-112
4.004 3-CI,5-CN Cl CF3 N02 NH2(i-C3H7)2~92-94
4.005 3-CI,5-CN Cl CF3 NO2 BzlN(CH3)3~ 135
4.006 3-CI,5-CN Cl CF3 N02 H3CN~n-C4H9)39 60-65
4.007 3-CI,5-CN Cl CF3 N02 NH(C2Hs)(i~C3H7)2~ 78-82
4.008 3-CI,S-CN Cl CF3 N0~ N(CH3)4~ l98
4.009 3-B~, 5-CN, ~ No2 CF3 K~ >230
4,6-lCH3)2
4.010 3-Br, 5-CN, H No2 CF3 N(CH3~4~ 213-220
4, 6-~CH3)2
4.011 3-8r, 5-CN, H No2 CF3 N(n-C4Hg)4~ 95-98
4,6-~CH3)2
4.012 3-CN, 5-Cr, H No2 CF3 N(n-C4Hg)4~ 94-96
4,6-( CH3)2
4.013 3-Cr, 5-CN H ~lO~ CF3 N(n-c4Hg)4~ 119-120
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54 _ o.Z. 0050/41896
EXP~LES OF USE
The insecticidal action of the compounds of the
formula I was demonstrated by the following tests:
The active ingredients were prepared
a) as 0.1 % s~rength solution in acetone or
b) a~ 10 ~ strength emuLsion in a mixture of 70 % by
weight cyclohexanol, 20 % by weight Nekanila LN
(Lutensol~ AP6, wettiny agent with emulsifying and
dispersing acticn ba~ed on etho~ylated alkylphenols)
and 10 ~ by weight Emulphor~ EL (Emulan0 E~, emulsi-
fier based on ethoxylated fatty alcohols~
and diluted to the required concen~ration with acetone in
the case of a) or with water in the case of b).
After completion of the test~, the lowest concen-
~ration of the compounds which still caused 80 - 100 ~
inhibi~ion or mortality compared with untreated control
test~ was determined (action threshold or minLmal concen-
tration (mg)).
A, Aphi~ fabae ~bean aphid) t contac~ action
Heavily ine~ ed young bean plants (Vicia faba) were
treated with aqueous formulations of the active ingredients.
The mort~lity ra~e was determined after 24 h.
In thi~ test, Compound~ 1.006, 1.009, l.ûll,
2.012, 2.017 and 2.023 had action threshold~ of from 20
to 1000 ppmO
B. Plutella maculipenni~ (cabbage moth caterpillar),
cont2ct action
Leaves of young cabbage plant~ were wetted with
the aqueou~ formulation of the actîve ingredien~ and then
placed on a moi~tened filter. 10 caterpillaxs of the 4~h
stage of development were then placed on each leaf.
The mortality ra~e was determined after 48 h.
In this ~est, Compound~ 1.004, 1.006, 1.009,
1.01~t 1.014, 1.017, 1.020, 1.034, 1.0~:6, 1.037, 2.005,
2.012, 2.013 and 2.017 had ac~ion thre~holds of from 100
to 1000 ppm.
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_ 55 _ o Z. 0050/41896
C. Tetranychus telarius (red spider mite),
contact action
Heavily infested beans in pots~ which had the
second pair of leaves, were sprayed to run-off ~ith
aqueous formulation~ of the acti~e ingredients.
After 5 days in a glasshouse, the success of
treatment was determined under a microscopeO
In this test, Compounds 1.006, 1.017, 1.020,
1.023, 1.036J 2.012 and 2.013 had action thre~hold~ of
from 20 to lO00 ppm.
D. Caenorhabditis elegans (free-living nematodes)~ con-
tact action
The soil of a te~t vessel was wetted with
solutionsof ~he ac~iveingredients in acetone and, aFter
the solvent had e~aporated off, covered with a ~uspension
of E. coli b~cteria a~ nutrient medium and in~ected with
50 ~l of nematod~ ~uspension.
The mortality rate wa~ determined after 4~ h.
- In thi~ test, Compound~ 1.002, 1.023, l.û28,
1.029, 1.030, 1.031 and ~.019 had action thre~holds of
from 4 to 100 ppm,
