CA2051298A1 - 2-anilinocyanopyridines and the use thereof for controlling pests - Google Patents

2-anilinocyanopyridines and the use thereof for controlling pests

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Publication number
CA2051298A1
CA2051298A1 CA002051298A CA2051298A CA2051298A1 CA 2051298 A1 CA2051298 A1 CA 2051298A1 CA 002051298 A CA002051298 A CA 002051298A CA 2051298 A CA2051298 A CA 2051298A CA 2051298 A1 CA2051298 A1 CA 2051298A1
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Prior art keywords
haloalkyl
alkyl
alkoxy
methyl
haloalkoxy
Prior art date
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Abandoned
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CA002051298A
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French (fr)
Inventor
Juergen Schubert
Christoph Kuenast
Uwe Kardorf
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BASF SE
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Individual
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/84—Nitriles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/84—Nitriles
    • C07D213/85—Nitriles in position 3

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pyridine Compounds (AREA)

Abstract

O.Z. 0050/41896 Abstract of the Disclosure: A method for controlling pests entails use of a 2-anilinocyanopyridine of the formula I

I

where X is nitro; cyano; halogen; alkyl; haloalkyl; alkoxy;
cycloalkyl; alkylsulfonyl; substituted or unsub-stituted phenyl, phenoxy or phenylthio, m is 1, 2 or 3, R1 is hydrogen; halogen; alkyl; haloalkyl; alkoxy;
haloalkoxy; substituted or unsubstituted phenoxy or phenylthio, R2 and R3 are each, independently of one another, hydrogen; nitro; cyano; carboxyl; halogen; alkyl;
haloalkyl; alkoxy; haloalkoxy; alkylthio; haloalkyl-thio; alkoxycarbonyl; alkylaminocarbonyl; dialkyl-aminocarbonyl; alkylsulfonyl; alkylaminosulfonyl;
dialkylaminosulfonyl;
R4 is hydrogen; formyl; alkyl; haloalkyl, alkenyl;
alkynyl; substituted or unsubstituted benzyl; COR5 or SO2R6;
R5 is alkyl; haloalkyl; alkoxy; haloalkoxy; alkylthio;
haloalkylthio; alkylamino; dialkylamino; substituted or unsubstituted benzyl, benzyloxy, benzylthio or benzylamino;
R6 is alkyl; haloalkyl; substituted or unsubstituted phenyl or benzyl;
and the salts thereof which can be used in agriculture.

Description

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)~

' . .
:- :
.
`
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) m Xm Rl R2 R3 H F CF3 N2 ,.

H H Cl NO~
H Cl Cl NO2 H H NO;~ C I

Cl Cl Cl 5-CI Br CF3 N2 5-C I OC4Hg ( n ~ CF3 ~2 5-CI oC6~14-P-CI CF3 N02 5-CI sc6H4-p-cl c~3 N2 - : : . . ~: .
. . .

- 25 - O. ~ . 0050/41896 TAE~LE A ( continuation ) Xm R ~ R
5-Cl H H Cl 5-Cl H Br NO2 5-CI H Cl NO2 5-CI ~ CONH2 No2 5-Cl H CON(CH3)2 N2 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 5-Cl H NO2 CF3 5-CI H NO2 Cl 5-CI H NOz CH3 5-CI Cl Cl NOz 5-Cl Cl Cl Cl 5-CI Cl H H
5-C~3 Cl C~3 NO2 5-CH3 F CF3 No2 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 S-Br H NO2 CH-C2H5 5-Br Cl Cl Cl 5-CF3 Cl CF3 NO2 5~CF3 F CF3 NO2 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 . OCH3 CF3 NO2 6-CI OC~H5 CF3 NO2 6-Cl O-n-C4Hg CF3 NO2 6-CI OCF2CHF~ CF3 N2 .
6 Cl OC6H5 C~3 ~2 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 : ;:

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 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 S2NH2 No2 6-CI H SO2N~CH3)2 No2 6-CI H C~CH3)3 No2 6-CI H 0CF2CHf2 N2 6-CI H N2 Cl 6-CI Cl Cl NO2 6 Cl Cl Cl Cl 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 H CF3 No2 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 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-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 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 ~' 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 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 COOC2Hs N2 H C 1 CONH2 No2 H H Cl NO2 H Cl Cl NO2 H H SO2CH3 No2 H H COOCH3 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 Br CF3 NO2 3-C I O-n-C411g CF3 N02 3-Ct oCf2cHF2 Cf3 N2 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 CONH2 No2 3-CI H CON(CH3)2 No2 3-Cl H COOCH3 No2 3-Cl Cl CN NO2 3-Cl Cl COOC2H5 No2 3-C I C I CONH2 No2 3-CI H 52CH3 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-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 3-Br H NO2 CH-C2Hg 3-Br Cl Cl Cl 33-CF~ Cf~ CF3 N02 3-CF3 H CF3 No2 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 6-CH3 Cl CF3 N02 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

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 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 ~ ~ ' , - :
.

- 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, .

52 - O. Z . 005Q/41~96 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 2 013 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 2.021 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 .. .

:
, ., :

2~ I 2~
- 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 .
' .

2~ 2~
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.

:
- :" ~` : ' .

, _ 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,

Claims (4)

1. A method for controlling pests, which comprises treating the pests or their habitat with an effective amount of a 2-anilinocyanopyridine of the formula I

I
where X is nitro; cyano; 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 aromatic groups in turn to carry from one to five halogen atoms and/or one to three of the following: C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4 alkylthio and C1-C4-haloalkylthio;
m is 1, 2 or 3, is being possible for the radicals to be different when m is 2 or 3;
R1 is hydrogen; halogen; C1-C4-alkyl; C1-C4-haloalkyl;
C1-C4-alkoxy; C1-C4-haloalkoxy; phenoxy or phenylthio, 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: C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio and C1-C4-haloalkylthio;
R2 and R3 are each, independently of one another, hydrogen; nitro; cyano; carboxyl; halogen; C1-C6-alkyl; C1-C6-haloalkyl; C1-C4-alkoxy; C1-C4-haloalkoxy;
C1-C4-alkylthio; C1-C4-haloalkylthio; C1-C4-alkoxy-carbonyl; C1-C4-alkylaminocarbonyl; di-C1-C4-alkyl-aminocarbonyl; C1-C4-alkylsulfonyl; C1-C4-alkylamino-sulfonyl; di-C1-C4 alkylaminosulfonyl;
R4 is hydrogen; formyl; C1-C6-alkyl; C1-C6-haloalkyl;
C3-C6-alkenyl; C3-C6-alkynyl; benzyl which in turn can carry from one to five halogen atoms and/or one to - 2 - O. Z . 0050/41896 three of the following: C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4 haloalkoxy, C1-C4-alkylthio and C1-C4-haloalkylthio;
COR5 or SO2R6 where R5 is C1-C6-alkyl; C1-C6-haloalkyl; C1-C4-alkoxy; C1-C4-haloalkoxy; C1-C4-alkylthio; C1-C4-haloalkylthio;
C1-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 a C1-C4 alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio and C1-C4-halo-alkylthio; and R6 is C1-C6-alkyl; C1-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: C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio and C1-C4-haloalkylthio, and the salts thereof which can be used in agriculture.
2. A method as claimed in claim 1, wherein the pests or their habitat are treated with an effective amount of a 2-anilinocyanopyridine of the fonmula I as claimed in claim 1, where R1 is hydrogen or halogen;
R2 and R3 are each, independently of one another, hydrogen; nitro; cyano; halogen; C1-C4-haloalkyl;
C1-C4-alkoxy or C1-C4-haloalkoxy;
R4 is hydrogen; COR? or SO2R8 where R5 is C1-C6-alkyl; C1-C6-haloalkyl; C1-C4-alkoxy; C1-C4-haloalkoxy; C1-C4-alkylthio; C1-C4-haloalkylthio;
C1-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: C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio and - 3 - O.Z. 0050/41896 C1-C4-haloalkylthio, and R6 is phenyl or benzyl, it being possible for the aromatic groups in turn to carry from one to five halogen atoms and/or one to thxee of the following:
C1-C4-alkyl, C1-C4 haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio and C1-C4-haloalkylthio, and the salts thereof which can be used in agriculture.
3. A method as claimed in claim 1, wherein the pests or their habitat are treated with an effective amount of a 2-anilinocyanopyridine of the formula I as claimed in claim 1, where R1 is hydrogen or halogen;
R2 and R3 are each, independently of one another, hydrogen; nitro; cyano; halogen or C1-C2-haloalkyl;
R4 is hydrogen or SO2R6 where R6 is phenyl which can carry from one to five halogen atoms and/or one to three of the following: C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio and C1-C4-haloalkylthio, and the salts thereof which can be used in agriculture.
4. The use of the compounds I as claimed in claim 1 for controlling pests.
CA002051298A 1990-09-20 1991-09-13 2-anilinocyanopyridines and the use thereof for controlling pests Abandoned CA2051298A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4029772A DE4029772A1 (en) 1990-09-20 1990-09-20 2-ANILINO-CYANOPYRIDINE AND THEIR USE FOR CONTROLLING Pests
DEP4029772.1 1990-09-20

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CA2102151A1 (en) * 1992-11-04 1994-05-05 Rikuo Nasu Method for halogenating an aromatic compound
DE4331179A1 (en) * 1993-09-14 1995-03-16 Hoechst Schering Agrevo Gmbh Substituted pyridines, processes for their preparation and their use as pesticides and fungicides
DE4331181A1 (en) * 1993-09-14 1995-03-16 Hoechst Schering Agrevo Gmbh Substituted pyridines, processes for their preparation and their use as pesticides and fungicides
TW200409629A (en) 2002-06-27 2004-06-16 Bristol Myers Squibb Co 2,4-disubstituted-pyridine N-oxides useful as HIV reverse transcriptase inhibitors

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ZA703779B (en) * 1969-06-12 1972-01-26 Ici Ltd Pesticidally active compounds and compositions containing them
US3799935A (en) * 1972-10-10 1974-03-26 Dow Chemical Co Substituted aminohalo-pyridines
JPS6052146B2 (en) * 1979-12-25 1985-11-18 石原産業株式会社 N-pyridylaniline compounds, their production methods, and pest control agents containing them
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DE4029772A1 (en) 1992-03-26

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