Title of Invention

N-THIO-ANTHRANILAMID COMPOUNDS AND THEIR USE AS PESTICIDES

Abstract N-Thio-anthranilamid compounds of formula (I) wherein A is a group selected from A1 and A2 wherein the variables and the indices are as defined per the description, processes for preparing the compounds I, pesticidal compositions comprising compounds I, use of compounds I for the control of insects, acarids or nematodes, and methods for treating, controlling, preventing or protecting animals against infestation or infection by parasites by use of compounds of formula I.
Full Text N-Thio-anthranilamid compounds and their use as pesticides
The present invention relates to N-Thio-anthranilamid compounds of formula (I)

wherein
R1 is hydrogen; or Ci-Cio-alkyl, C2-Cio-aikenyi, C2-Cio-aikynyi, or C3-Ce-cycloa!Kyl,
each of which is unsubstituted or substituted with 1 to 5 groups independently.se-
lected from halogen, cyarto, nitro, hydroxy, Ci-Cio-alkoxys CrCio-alkylthio, C1-C10-
alkyisulfinyl, Ci-Cio-alkylsu!fonyl, C2-Cio-alkoxycarbonyl, Ci-C10-alky!amino, di(C-i-
Cio-alky!)amino and Cs-Cs-cycioaikyiamino; or Ci-C-io-alkylcarbonyl, C1-C10-
alkoxycarbonyl Ci-C-io-alkyiaminocarbonyl, di(Ci-Cio-aIkyi)aminocarbonyi;
A is a group selected from A1 and A2


wherein
# denotes the binding site;
R2 and R3 each independently are Rs, -C(=G)R7, -C(=NOR7)R7, -C(=NNR72)R7, -
C(=G)OR7, -C(=G)NR72, -OC(=G) R7, -OC(=G)OR7, -NR7C(=G)R7, -N[C(=G)R7]2,
-NR7C(=G)OR7, -C(=G)NR7-NR72, -C(=G)NR7-NR7[C(=G)R7]I -NR7-C(=G)NR72, -
NR7-NR7C(=G)R7, -NR7-N[C(=G)R7]2, -N[(C=G)R7]-NR72, -NR7-NR7[(C=G)GR7], -
NR7[(C=G}NR72, -NR7[C=NR7]R7, -NR7(C=NR7)NR72t -0-NR72, -0-NR7(OG)R7, -
S02NR72, -NR7S02R7, -S02OR7, -OS02R7, -OR7, -NR72, -SR7, -SiR73, -PR72, -
P(=G)R7, -SOR7, -SOjR7, -PG2R72, or -PG3R72; or
R2 and R3 together with the sulfur atom to which they are attached form a saturated,
partially unsaturated or unsaturated 3- to 8-membered ring which contains 1 to 4
heteroatoms selected from oxygen, nitrogen, sulfur, which ring can be fused with
one or two saturated, partially unsaturated or unsaturated 5- to 6-membered rings
which may contain, 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur,

2
wherein ail of the above rings are unsubstituted or substituted by any combination
of 1 to 6 groups R8;
G is oxygen or sulfur;
R6 is Ci-C20-alkyl, C2-C2o-alkenyl, C2-G20-aikynyi, C3-Cs-cycloaikyl, C3-C8-
cycloalkenyl, C3-Cs-cycfoalkyny[, phenyl, naphthyi, bipheny!, or a saturated, par-
tially unsaturated or unsaturated 3- to 8-membered ring system which contains 1
to 4 heteroatorns selected from oxygen, nitrogen, sulfur, wherein all of these
groups are unsubstituted or substituted by any combination of 1 to 8 groups R8;
R' is hydrogen or Rs;
R8 is R9; or two groups Rs together with the atoms to which they are attached form a
saturated, partially unsaturated or unsaturated 3- to 8-membered ring system
which may contain 1 to 4 heteroatorns /heterogroups selected from oxygen, nitro-
gen, sulfur, SO and SO2, and which ring system is unsubstituted or substituted
with any combination of 1 to 6 groups R9.
R9 is R1D, R11, -C C(=G)NR1°2, -OC(=G) R10, -OC(=G)OR10, -NR10C(=G)R10, -N[C(=G)R10j2, -
NR10C(=G)OR10, -C(=G)NR10-NR102, "C(=G)NR10'NR10[C(=G)R10], -NR10-
C(=G)NR102, -NR10-NR10C(=G)R10, -NR10-N[C(=G)R1D]2, -N[{C=G)R1°]-NR™2, -
NR10-NR10[(C=G)GR10], -NR10[(C=G)NR102, -NR1°[C=NR10]R10, -
NR10(C=NR10)NR102, -O-NR102, -O-NRl0(C=G)R10, -S02NR1Q2, -NR10SO2R10, -
S020R10, -OSO2R10, -OR10, -NR102, -SR10, -SiR1°3, -PR102, -P(=G)R10, -SOR10, -
SO2R10, -PG2R1D2, -PG3R1°2, or two groups R9 together are (=G), {=N-R10),
(=CR1°2), (=CHR10), or (=CH2);
R10 is CrCio-alkyl, Cu-Cio-alkenyl, C2-C10-alkynyl, C3-C8-cycloalkyi, C4-C8-
cycloalkenyl, C3-C8-cycloalky[- Ci-C4-aikyl, C4-Ce-cycloalkenyl-C-i-C4-aikyl, C3-C8-
cycioalkyl-C2-C4-aikenyl, C4-CB-cycloaikenyl-C2-C4-alkenyl, C-rCio-aIkyl-p3-C8-
cydoalkyl, C2-Cio-a!keny!-C3-Cs-cycloalkyl, C2-C-io-atkynyI-C3-Ce-cycloalky!, Cr
C10-aikyl-C4-C8-cycloalkenyl, C2-Cio-alkenyi-C4-CB-cyc!oalkenyl, C2-Cio-alkynyl-C4-
CB-cycloalkenyl,
a saturated, partially unsaturated or unsaturated 3- to 8-membered ring system
which contains 1 to 4 heteroatorns selected from oxygen, nitrogen, sulfur,
wherein the above groups are unsubstituted or substituted with any combination
of from 1 to 6 groups R11;
R11 is halogen, cyano, nitro, hydroxy, mercapto, amino, formyl, Ci-C10-alkylcarbony!,
CrCio-alkoxy, C2-Cio-alkenyloxy, C2-Cio-aIkynyioxy, Ci-Cio-haloalkoxy, C3-C10-
haloalkenyloxy, C3-Cicnhaloalkynyloxy, C3-C8-cycloafkoxy, C4-Cs-cyc!oalkenyloxy,

3
C3-Cs-halocycloa!koxy, CCg-halocydoalkenyloxy, Cs-Cs-cycloalkyl- Ci-C4-alkoxy,
C4-Ce-cycloalkenyl-C-i-C4-aikoxy, C3-C3-cycloalky[- C2-C4-alkenytoxy, C4-C8-
cyc!oa!kenyl-C2-C4-a[kenyloxy, Ci-Cio-a!kyl-C3-Cs-cycloalkoxy, Ci-Cio-alkenyl-C3-
Cs-cycloalkoxy, Ci-Cio-alkynyi-Cs-Cs-cycloafkoxy, Ci-Cio-alky!-C3-Cs-
cycloalkenyloxy, CrCi0-atkeny[-C3-C8-cycloalkenyloxy, CrC4-aIkoxy-C-rCio-
alkoxy, Ci-C4-alkoxy-C2-Cic>-a!keriyloxy, mono- or di(Ci-Cio-alkyl)carbamoy!,
mono- ordi(C-i-Cio~iiaioalkyl)carbarnoyl, mono- or d!(C3-C3-cycioa!ky!)carbamoy!,
CrCio-alkoxycarbonyl, CCs-cydoalkoxycarbonyl, C-i-Cio-a!ky!carbony!oxy, C3-
Cs-cycio alkylcarbonyioxy, CrCio-haioa!koxycarbony!, C1-C10-
haioaikyicarbonyloxy, Cr-Cio-a!kanamido, Ci-Cio-haloalkanamido, C2-C10-
aikenarnido, C3-Cs-cycloalkanamido, C3-Ce-cycioafkyi-Ci-C4-alkanamido,
CrCio-alkyithio, Cp-Cig-aikehylthio, C2-Cio-alkynylthio.. CrCio-haloalkyithio, C2-
Cio-ha!oa!ksnySthio, CrCio-haioalkynylthio, Cs-Cs-cycIoalkylthio, C3-CB-
cyebalkenylthio. Cs-Ca-halocycloalkylthio, C3-Cs-haiocyc!oa!kenySthio, C3-C8-
cycloalkyl- CrC4-alky]thio, C4-C8-cycfoaikenyl-Ci-C4-alkyJthio, Cs-Cs-cycloalkyl-
C2-C4-alkenylthio> C4-C8-cyc!oalkeny!-C2-C4-alkenyIthio, C-i-Cio-alkyi-C3-C8-
cycloalkylthio, Ci-Cio-alkenyl-C3-Cs-cycloalkylthio, Ci-Cio-a!kyny!~C3-CB-
cycloalkyithio, Ci-Cio-alky[-C3-C6-cycIoa!kenylthio, Ci-Ci0-alkeny[-C3-C8-
cycloalkenylthio, Cj-C-io-alkyisulfinyl, C2-Cio-alkenyisuifinyl, CCio-alkynylsulfinyl,
CrCio-haioalkyisulfmyi, C2-Cio-haioaIkenyisu!finyi, C2-Cio-haloaikynylsulfinyl, C3-
Cs-cycloalkyisulfinyi, C3-CB-cycioalkeny!sulftny!, C3-Cs-haSocycioaikylsulfinyl, C3-
Cs-hafocycloalkenyteuifinyi, C3-C&-cycloalkyi- Ci-C4-aiky[su!finyI, C4-Cs-
cycloatkenyl-CrC4-alkyisulfinyl, C3-C8-cycloalkyi- C2-C4-alkenylsulfinyl, C4-C8-
cycloaikeny]-C2-C4-alkenyisulfinyl, Ci-Cio-a!kyl-C3-Ce-cycioalkylsulfinyl, C1-C10-
aikenyl-C3-C8-cycIoalkylsuSfinyf, Ci-Cio-alkynyl-C3-C8-cycioaikytsuifinyf, C1-C10-
alky!-C3-C8-cyc!oaikenyIsuifinyl, Ci-Ci0-a!kenyl-C3-Cs-cyc!oalkenylsulfiny!, C1-C10-
alkylsulfonyl, C2-Ci0-alkenylsulfonyl, C2-Ci0-alkynyisuifonyl, C1-C10-
haloalkylsulfonyl, C2-Ci0-ha!oalkenylsulfonyl, C2-Cio-haloalkynyisulfonyl, C3-C8-
cycioafkylsulfcnyl, C3-Cs-cycIoalkeny!sulfonyl, C3-Ce-halocycIoafky[sulfony!, C3-CS-
halocycloalkenylsulfonyl, C3-C3-cycloalkyl- Ci-C4-alkylsulfonyi, C4-Cs-cycloalkenyl-
CrC4-a!kylsulfony!, Cs-Cs-cycloalkyl- C2-C4-alkenyIsulfony!, C4-C8-cycloalkeny!-C2-
Ci-alkenylsulfonyl, CrC-io-a!kyl-C3-C8-cycloalkylsu[fonyf, C-i-Cio-alkenyl-C3-Ca-
cycioalkylsuifony!, CrC-alkynyl-Cs-Cs-cydoalkylsulfonyt, Ci-Cio-a!ky!-C3-C8-
cycloalkenytsuifonyi, CrCio-alkenyl-C3-C8-cyc[oaikenylsulfonyi, di(Ci-Cio-
alkyl)amino, CrCi0-alky!amino, C2-Ci0-a!keny!amino, C2-Cio-aIkynylamino, Ci-C10-
alkyl-C2-Cio-alkeny!amino, Ci-Cio-aIkyKVCio-aIkynylamino, C1-C10-
hatoaikylamino, C2-Cio-haloalkenyIamino, C2-Cio-haloalkynylamino, C3-Cs-
cycloaikylamino, C3-C8-cyc!oalkeny!amino, C3-C8-halocycloalkylamino, C3-C8-
halocycloalkenylamino, C3-C8-cycbalkyl- Ci-C4-a!kyIamino, C4-C8-cycloalkeny!-Cr
C4-a!kylamino, C3-Cs-cycJoa]kyI- C2-C4-aIkenylamino, C4-C3-cycloalkenyJ-C2-C4-
atkenylamino, Ci-Gio-alkyl-C3-Cs-cycloalkylarhino, Ci-Ci0-alkenyl-C3-Cs-
cycioaikylamino, CrC'io-alkyny!-C3-Ce-cycloalkytamino, Ci-Cio-alkyl-Cs-Cs-

4
cycloafkenylarnino, d-do-alkenyl-d-Cs-cycloalkenyiamino, trKd-do-aikyOsifyl
aryl, aryloxy, arylthio, arylamino, aryl-d-d-alkoxy, aryl-C3-d-aikenyloxy, aryl-C-r
d-aikyithio, aryl-C-2-d-alkenylthio, aryl-d-d-alkylamino, aryl-C3-d-
afkenylamino, ary!-di(Ci-C4-alkyl)silyi, tharylsifyl, wherein aryl is phenyl, naphihyl
or biphenyl, or
a saturated, partialiy unsaturated or unsaturated 3- to 8-membered ring system
which contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur,
wherein these aryl and these heterocyclic ringsystsrns are unsubstituted or substi-
tuted with any combination of from 1 to 6 groups selected from halogen, cyano, ni-
tro, amino, hydroxy, mercapto, GrG4-a!kyl, Ci-C4-haloa!kyl, C3-Ce-cyc!oa!kyl, d-
C4-alkoxy, d-d-ha!oa!koxy, CyC4-a!kyiihio, Gi-C4-haloalky!thiot di(d-d-
aSky!)amino, d-d-alkylamino, Ci-C4-hatoalky!amino, formyl and d-d-
alkylcarbonyl;
R* is NW2R;
R12and R13 are each independently hydrogen; or C1-C2o-alkyl, C2-C2o-alkenyi or
C2-C2o-a!kynyi, each of which is unsubstituted or substituted with any combination
of 1 to 6 groups selected from d-d-alkoxy, Ci-C4-alkylthio, cyano, nitro, formyl,
Ci-C4-alkylcarbonyi, CrC4-alkoxycarbonyl, d-d-alkylaminocarbonyl, di(d-d-
alkyl)aminocarbonyl, d-d-alkyisulfinyl, d-d-alkylsulfonyl, ds-drcycioaikyl, and
phenyl, wherein phenyl itself is unsubstituted or substituted by i to 4 substituenis
selected from halogen, d-d-alkyl, CrC4-a[koxy, Ci-C4-fluoroalkyl, d-d-
alkyloxycarbonyl, trifluoromethylsulfonyl, formyl, nitro and cyano; or
Ci-C2o-haloa!kyl, C2-C2o-ha!oalkenyl, C2-C2o-haloalkynyi, d-do-cycloa!kenyl, or a
saturated or partially unsaturated or unsaturated 3- to 8-membered ring system
which contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur, or
phenyl or naphthyl, wherein this ring system and phenyl or naphthyl themselves
are unsubstituted or substituted by 1 to 4 substituents selected from halogen, d-
C4-aikyl,- Ci-C4-alkoxy, d-d-fluoroalkyl, d-d-alkyioxycarbonyl, trifluoromethyl-
sulfonyl, formyl, nitro and cyano; or
R12 and R13 together with the nitrogen atom to which they are attached form a
saturated or partially unsaturated 5- to 8-membered heterocycle which besides
the one nitrogen atom contains 0 to 2 further heteroatoms selected from oxygen,
nitrogen, sulfur, and may contain 1 or 2 carbonyl groups or thiocarbonyl groups
and which is unsubstituted or substituted by from 1 to 4 groups selected from d-
d-alkyl, d-d-alkoxy and d-d-haloalkyl;
R5 is hydrogen; or d-C2o-alkyl, d-do-alkenyl, C2-C2o-a!kynyl, d-d-alkyicarbonyl,
d-d-alkylaminocarbonyl, d-d-alkoxycarbonyl, each of which is unsubstituted or

5
substituted by from 1 to 6 groups selected from Crd-alkoxy, Ci-Calkylthio,
cyano, nitro, formyl, Ci-C4-aikylcarbonyl, Ct-C4-aJkoxycarbonylJ C1-C4-
alkylaminocarbonyi, di(Ci-C4-aikyi)aminocarbonyl, C-rC4-a!kylsuifinyl, C1-C4-
alkylsulfonyt, Ca-Cs-cycloalkyl, and phenyl, wherein phenyl itself is unsubstituted
or "substituted by 1 to 4 substituents selected from halogen, Ci-C4-aikyi, C1-C4-
alkoxy, Ci-C4-fiuoroalkyl, Ci-C4-atkyloxycarbonyl, trifluoromethylsulfonyl, formyl,
nitro and cyano; or •
CrC2o-haloalkyi, C-Cao-haioaikenyl, C2-C2o-haloaikynyiJ Cs-Cio-cycloalkenyl, or a
saturated or partiaiiy unsaturated or unsaturated 3- to 8-membered ring system
which contains 1 to 4 heteroatoms selected from oxygen, nitrogen, suifur, or
phenyl or napnihyi, wherein this ring system and phenyl or naphthyl themselves
are unsubstituted or substituted by 1 to 4 substituents selected from halogen, C1-
C4-alky{! Ci-C4-a(koxy, CrC4-fluoroalkyl, Ci-Cva!ky!oxycarbonyl, trifluoromethyi-
sulfonyi, formyl, nitro and cyano;
Q1 and Q2 each independently are hydrogen, halogen, cyano, SCN, nitro, hydroxy, Ci-
Cio-alkyl, Ci-Cio-haloalky!, C2-Ci0-a!kenyI, C2-Cio-ha!oalkenyl, C2-Cio-alkynyl, C3-
Cto-haloalkynyl, C3-Ce-cycloaIky[, C3-Cs-haiocycloalkyI, CrCto-alkoxy, C1-C10-
haioalkoxy, CrCio-alkylthio, Ci-Cio-haloalkylthio, Ci-Ci0-alkylsulfinyi, C1-C10-
haloaikylsuifinyl, d-Cio-alkylsulfonyl, Ci-Cio-haloaJkylsulfonyl, C1-C10-
alkylsulfonyioxy, Ci-Cio-haloalkylsuifonyloxy, Ci-Cio-aikylamino, di(CrC-io-
a!kyl)amino, Cs-CB-cyciaikylamino, alkylcarbonyl, Ci-Cio-alkoxycarbonyi, C1-C10-
alkylaminocarbonyl, di(CrCio-alkyl)a!T|inocart|onyi, or tri(Ci-Cw)-aIkylsilyl, or
Q1 and Q2 are each independently phenyl, benzyl or phenoxy, wherein each ring is un-
substituted or substituted with any combination of from 1 to 3 substituents inde-
pendently selected from the group halogen, cyano, nitro, Ci-Cuj-alkyl, C1-C10-
haloalkyl, C2-Cio-alkenyl, C2-Cio-haloalkenyl, C2-Cio-a!kynyl, C3-Cio-haloatkynyl,
C3-C8-cycloalkyl, C3-C8-halocyc!oalkyf, CrC-io-alkoxy, CrCurhaioalkoxy, C1-C10-
alkytthio, Ci-Ci0-alkylsulfinyl, d-Cio-alkylsulfonyl, C-i-C-io-alkylamino, di(Ci-C-io-
aiky!)amino, C3-C8-cycloalky!amino, CrCi0-a!kyl-C3-C8-cycloaJkyIamino, CrCio-
alkylcarbonyi, Ci-Cio-alkoxycarbonyi, CrCio-alkylaminocarbonyl, di(C-i-Ci0-
alkyl)aminocarbonyl and tri(C-rCio)-alkylsilyl;
Q3 is halogen; or Ci-C10-atkyl, CrC-io-haloalkyl, C2-Cio-a(kenyl, C2-Cio-haIoalkenyl,
C2-Cio-alkynyl, C3-Cio-haloaikynyl, C3-C3-cycIoalkyl, C3-C8-halocycloalkyi, C1-C10-
a!ky!-C3-C6-cycloafkyl, Ci-Cia-haloa!kyi-C3-C8-cycloalkyl, each unsubstituted or in-
dependently substituted with 1 to 2 groups selected from cyano, CrCio-alkoxy,
Ci-do-haloalkoxy, Ci-Cio-alkylthio, Ci-Cio-haloalkylthio, CrC10-a!kylsu[finy!, d-
Cio-haioalky!sulfinyl, Ci-Cio-alkyisulfonyl, Ci-Cio-ha!oalkylsu!fonyl, and C1-C10-
alkoxycarbonyl; or

6
Q3 is OR14, S(0)qR1«, NR15R16, OS(0)2R17, NR15S(0)2R17, C(S)NH2) C{R16)=NOR1B,
. C3-Cs-cycloalkyl-CrC4-alkyl, Ci-Cio-a!kylaminothiocarbonyl, ordi(CrCio-
alkyl)aminothiocarbonyl;
R14 is d-do-alkyf, Ci-do-haloafkyf, d-do-alkenyl, C2-do-ha!oalkeny!, C2-C10-
alkynyl, C3-Cio-haloalkyny!, d-CB-cycloalkyi, C3-Cs-halocycloalkyt, C3-C8-
cyc!oaikyi-Ci-C4-alkyl, Ci-C4-alkyi-C3-C8-cycloalkyi, Cs-Cs-halocycloalkyl-Ci-CV
alkyl, Ci-haloalkyl-Cs-Cs-cycloalkyl, or d-Cio-haloalkylcarbonyJ, each
unsubstituted or substituted with 1 R19;
R15 is d-Curalkyl, Ci-Ci0-haloalkyl, C2-d0-alkenyi, C2-Cio-haloaikenyl, C2-Ci0-
alkyny!, C-a-Cio-habalkynyi, Ca-Cs-cydoalkyl, Cs-Cs-halocydoalkyl, Ci-G4-alkyl-C3-
Cs-cycioalkyl, d-d-haloalkyi-Cs-Cs-cyctoalkyl, or Ci-Cio-ha!oalkylcarbony!, each
unsubstituted or substituted with i R1i3;
R1S is hydrogen; or Ci-C10-alky(, d-do-haioalkyl, C2-Ci0-alkenyl, C2-do-
haioaikenyi, C2-Cio-alkynyl, C3-do-haioalkynyl, C3-Ce-cycloalkyl, C3-Cs-
haiocycloalkyl, CrC4-a!ky[-C3-Ca-cycIoa[kyI, or d-d-hafoalkyl-d-Ca-cycIoalkyl,
each unsubstituted or substituted with 1 R19;
R17 is Ci-Cio-alkyl, Ci-Ci0-ha!oaIkyl, C2-Cio-alkenyl, C2-Ci0-ha!oaSkenyl, C2-C10-
alkynyl, C3-Cio-haloaIkyny!, C3-Cs-cycIoa!kyf, C3-CB-halocycloalkyl, Crd-alkyl-d-
Cs-cycloalkyl, or Ci-C4-haloalkyl-C3-Cs-cyc!oaiky!, each unsubstituted or
substituted with 1 R19;
R19 is cyano, nitro, CrC-io-alkoxy, Ci-Cio-haloalkoxy, CrCio-alkylthio, d-Cio-
haloalkylthio, Ci-Cio-alkylsulfinyl, d-do-haloalkyisulfinyl, C1-C10-
alkylsul'fonyl, Ci-do-haloalkylsulfonyl, Ci-Cio-alkoxycarbonyl, C1-C10-
alkylamino, or di(Ci-Cio-alkyl)amino; or
R19 is phenyl or a heteroaromatic 5- or 6-membered ring which contains 1 to
4 heteroatoms selected from oxygen, nitrogen, sulfur, the phenyl radical and
the heteroaromatic ring being unsubstituted or substituted with any
combination of from 1 to 3 groups selected from halogen, cyano, nitro, d-
do-alkyl, d-do-haloalkyl, drdo-alkenyi, C2-Cio-haloalkenyl, d-do-alkynyl,
" C3-do-haloaikynyl, C3-Cs-cycloalkyl, C3-CB-ha!ocycloa!kyi, Crdo-alkoxy, d-
Cio-haloalkoxy, CrCio-alkylthiOj Ci-Cio-alkylsulfinyl, CrCio-alkylsulfony!, d-
Cio-alkylamino, di(Ci-dcraikyl)amino, C3-C6-cycloalky!amino, CrCio-aIkyI-
C3-Cs-cycIoalky!amino, d-do-aikylcarbonyl, Ci-Cio-alkoxycarbonyl, C1-C10-
aikylaminocarbonyl, di(Ci-Cio-alkyl)aminocarbonyl and tri(Ci-Cio)-a!kylsily!;

7
R1B is the same or different: hydrogen, Ci-Cio-alkyl, or Ci-Cio-haJoalkyl;
q is 0, Tor2;
Q4 is halogen, cyano, nitro, hydroxy, COOH, C(0)NH2, CrCio-alkyl, Ci-Cio-haloalkyl,
C2-C10-alkenyl, C2-Cio-haloalkenyl, C2-Ci0-aikynyl, C3-Cio-haloalkynyl, C3-Ce-
cycioalky!, C3-C8-halocycloa!kyl, d-Cio-alkoxy, Ci-C-io-haloaikoxy, C1-C10-
alkylthio. C-i-Cio-haloalkylthio, Crdo-aikylsulfinyl, Ci-Cio-haioa!kyisu!finyl, Ci-Cio~
alkylsulfonyl, Ci-C-io-haloaSkylsulfonyl, C-t-C-io-aikylamino, di(Cr-Cio-aikyl)amino,
C3-C3-cycloaikyIamlno, Ci-Cio-alkylcarbonyl, Ci-Cio-alkoxycarbony! C-1-C10-
aikyiaminocarbonyi, di(CrCio-aikyi)arriinocarbonyl or tri(C1-Cio)-aiky!sily!; or
Q4 is phenyl, benzyl, benzyloxy, phanoxy, a 5- or 6-membered heteroaromatic ring
which contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur or an
aromatic 8-, 9-or 10-membered fused heterobicyclic ring system which" contains 1
to 4 heteroatoms selected from oxygen, nitrogen, sulfur, wherein each of the
above ring systems is unsubstituted or substituted with any combination of from 1
to 3 groups selected from halogen, cyano, nitro, Ci-Cio-alkyl, CrCio-ha!oalkyl, C2-
do-alkeny!, C2-Cio-haloalkenyf, C2-Cio-a!kynyl, C3-Cio-haloalkynyl, Cs-Cs-
cycloalkyl, Cs-Ce-haiocycloalkyl, CrCio-alkoxy, Ci-Cio-haloalkoxy, CrCio-
alkyithio, Ci-Cio-~alkyIsulfinyS, CrCio-alkylsulfonyl, CrCio-alkyfamino, di(Ci-Cio-
alkyl)amino, C3-Ce-cycloalkylamino, d-Cio-alkyl-Cs-Cs-cycioalkylamino, C1-C10-
alkylcarbonyl, CrC-alkoxycarbonyl, Ci-Cio-alkylaminocarbonyl, di(CrCio-
a!kyl)aminocarbonyl and tri(C-rCio)-alky!si!yI;
X and Y are each independently oxygen or sulfur;
V and V are each independently N or CQ2;
W is.N, CHorCQ4;
m is 0, 1 or 2;
n is 0 or 1;
p is 0, 1,2, 3, or 4;
or the enantiomers or salts or N-oxides thereof.
In addition, the present invention relates to processes for preparing the compounds I,
pesticidal compositions comprising compounds I arid methods for the control of insects,
acarids or nematodes by contacting the insect, acarid or nematode or their food supply,

8
habitat or breeding grounds with a pestictdalfy effective amount of compounds or com-
positions of formula !.
Moreover, the present invention also relates to a method of protecting growing plants
from attack or infestation by insects or acarids by applying to the fofiage of the plants,
or to the soil or water in which they are growing, with a pesticidally effective amount of
compositions or compounds of formula I.
This invention also provides a method for treating, controlling, preventing or protecting
animals against infestation or infection by parasites which comprises orally, topically or
parenteraily administering or applying to the animals a parasiticidally effective amount
of compositions or compounds of formula i.
in spite of the commercial Insecticides, acarlcides and nematic-ldes available today,
damage to crops, both growing and harvested, caused by insects and nematodes sti!!
occurs. Therefore, there is continuing need to develop new and more effective insecti-
cidal, acaricidai and nemsticidai agents.
It was therefore an object of the present invention to provide new pesticidal composi-
tions, new compounds and new methods for the control of insects, acarids or nema-
todes and of protecting growing pfants from attack or infestation by insects, arachnids
or nematodes.
We have found that these objects are achieved by the compositions and the com-
pounds of formuia I. Furthermore, we have found processes for preparing the com-
pounds of formula I.
Anthraniiamide compounds have been described in a number of patent applications
(WO 01/70671, WO 03/015518, WO 03/015519, WO 04/046129). N-Thio-
anthranilamide compounds have not been described in the prior art.

can be prepared by reacting a carboxylic acid of the formula (I!)
Compounds of the formuia (1-1) wherein X and Y are oxygen and the other substituents
are as defined above for formula (I)

9

wherein the variables are as defined for formula (!) in the form of an activated deriva-
tive of this acid in the presence of a base with a compound of the formula A1-H or A2-H,
respectively, wherein the variables are as defined for formula (i).

Suitable activated derivatives of the acid which may be used are, for example, anhy-
drides, azoiides, or acid haiides.
The activated derivatives of the acid can be obtained according to procedures known in
the art, e.g. as listed in "Comprehensive Organic Reactions" VCH Publishers 1989, for
the anhydride: pp 965-66, for the acid haiides: p 978.
Suitable bases are, for example, amines such as triethylamine, diisopropylethyiamine,
pyridine or iutidine or efse alkali hydrides, hydroxides, carbonates, or alkaline earth
metal hydroxides, carbonates or bicarbonates.
The amount of the base that can be used in the reaction is usually 1 to 5 moles relative
to 1 mole of compound (ll).
The reaction is advantageously carried out in an inert solvent such as dichloromethane,
chloroform, carbon tetrachloride, benzene, toluene, diethyl ether or tetrahydrofurane, or
mixtures of these solvents, in a temperature range between 0°C and 100°C, preferably
between 20DC and 50°C.
A preferred procedure for the preparation of specific compounds of formula (1-1) in-
volves the reaction of A1-H or A2-H, respectively, with a benzoxazinone of formula (111)


10
wherein the variables are as defined for formula (!), Typical procedures involve combi-
nation of the compounds A1-H or A2-H with the benzoxazinone of formula (HI) in inert
solvent such as dichloromethane, chloroform, carbon tetrachloride, benzene, toluene,
diethyl ether or tetrahydrofurane. or mixtures of these solvents, In a temperature range
hetweenCTC and 1Q0°C, preferably between 20°C and 50 °C. Addition of a base can
be beneficial. Suitable bases are, for example, tertiary amines such as trielhylamine,
diisopropylethylamine, pyridine or iutidine or else alkali hydrides, hydroxides, carbon-
ates, or alkaline earth metal hydroxides, carbonates or bicarbonates. The amount of
the base that can be used in the reaction is usually 1 to 5 moles relative to 1 mole of
compound (III).
Benzoxazinones are well documented in the chemical literature and are available via
known methods that involve the coupling of either an anthranilic acid or an isatoic an-
hydride with an acid chloride. For references to the synthesis and chemistry of ben-
zoxazinones see Jakobsen et al, Bioorganic and Medicinal Chemistry, 2000, 8, 2095-
2103 and references cited therein. See also Coppola, J. Heterocyclic Chemistry, 1999,
36, 563-588. The benzoxazinones of formula Hi can also be prepared according to the
procedures described in WO 04/046129 or WO 04/011447 as well as according to ref-
erences cited therein and suitable modifications thereof.

can be prepared by reacting an amide of the formula (IV)
Compounds of the formula (I-2) in which A is A1, n is 0, X and Y are oxygen and the
other variables are as defined for formula (I),



11
wherein the variables are as defined for formula (I), with a sulfoxide of the formula (V),
in the presence of a condensating agent giving the compounds of formula (I-2) with
elimination of water. Suitable condensing agents are, for example, phosphorous oxy-
chioride, phosphorous (V) oxide,methanesulfonyl chloride, sulfuryl chloride, sulfur tri-
chloride, boron irifiouride, dicyclohexylcarbodiimide, aryl cyanates or acid anhydrides,
preferably triflouroacetic anhydride or triflouromethanesulfonic anhydride.
In the compounds of the formula (I) prepared as described above in which A is A1, n is
0, X and Y are oxygen and the other variables are as defined for formula (i) the sulfur
atom can be oxidized to give the respective compounds of the formula (i) in which n is
1. Suitable oxidizing agents are, for example, sodium periodate or organic peracids,
such as 3-chloroperbenzoic acid, see e.g. Houben-Weyl, Methoden der Organischen
Chemie, Bd. E11, p. 1299 ff., G. Thieme Verlag, Stuttgart 1985.
The carboxylic acids of formula (II) and the amides of formula (IV) can be prepared, for
example, according to the procedures described in WO 04/046129 or WO 04/011447
as well as according to references cited therein and suitable modifications thereof.
After completion of the reaction, the compounds of formula I can be isolated by em-
ploying conventional methods such as adding the reaction mixture to water, extracting
with an organic solvent, concentrating the extract an the like. The isolated compound
(I) can be purified by a technique such as chromatography, recrystailization and the
like, if necessary.
Compounds of formula A1-H can be prepared according to procedures known in the
art, e.g. as decribed in US 6 136 983 and references cited therein.
Compounds of formula A2-H can be prepared according to procedures known in the
art, e.g. as described in WO 03/097589 and references cited therein.
Sulfoxides of formula V can be obtained according to procedures known in the art, e.g.
as described in J. March, Advanced Organic Chemistry, 4m Edition, Wiley, 1992, p.
1297.

12
Compounds of formula i, ll, ill, IV, V, and compounds A1-H and A2-H which cannot be
prepared according to the above procedures can be prepared according to suitable
modifications of the above procedures.
The preparation of the compounds of formula I above may lead to them being obtained
as isomer mixtures. If desired, these can be resolved by the methods customary for
this purpose, such as crystallization or chromatography, also on optically active adsor-
bate. to give the pure isomers.
Agronomically acceptable salts of the compounds I can be formed in a customary
manner, e.g. by reaction with an acid of the anion In question.
in this specification and in the claims, reference wis) be made to a number of terms that
shall be defined to have the following meanings:
"Salt" as used herein includes adducts of compounds i with maieic acid, dimaleic acid,
fumaric acid, difumaric acid, methane sulfenic acid, methane sulfonic acid, and succinic
acid. Moreover, included as "salts" are those that can form with, for example, amines,
metals, alkaline earth metal bases or quaternary ammonium bases, including zwitteri-
ons. Suitable metal and alkaline earth metal hydroxides as salt formers include the
salts of barium, aluminum, nickel, copper, manganese, cobalt zinc, iron, silver, lithium,
sodium, potassium, magnesium or calcium. Additional salt formers include chloride, .
sulfate, acetate, carbonate, hydride, and hydroxide/Desirable salts include adducts of
compounds I with maieic acid, dimaleic acid, fumaric acid, difumaric acid, and methane
sulfonic acid.
"Halogen" will be taken to mean fluoro, chloro, bromo and iodo.
The term "alky!" as used herein refers to a branched or unbranched saturated hydro-
carbon group having 1 to 10 carbon atoms, such as, and preferably, Ci-Cs-alkyl, for
example methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-
dimethylethyl, pentyl, 1-methyfbutyf, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropy!,
1-ethyipropyl, hexyl, 1,1-dimethyipropyl, 1,2-dimethyipropyl, 1-methytpentyl, 2-
methylpentyl, 3-methylpentyl, 4-methylpentyi, 1,1-dimethylbutyl, 1:2-dimethylbutyl, 1,3-
dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-
ethytbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methySpropyI and 1-
ethy l-2-methy [propyl.
The term "haloalky!" as used herein refers to a straight-chain or branched alkyl group
having 1 to 10 carbon atoms (as mentioned above), where some or all of the hydrogen
atoms in these groups may be replaced by halogen atoms as mentioned above, for
example d-C2-haloalkyl, such as chloromethyi, bromomethyl, dichloromethyl, tri-

13
chioromethyl, fluoromethyl, dif!uoromethyl, triftuoromethyl, cblorofluorometbyl, dichloro-
fiuoromethyl, chlorodifluoromethy!, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-
.fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifiuoroethyl, 2-chloro-2-f!uoroethyl, 2-chton>2,2-
difluoroethyl, 2,2-dichloro-2-fiuoroethyl, 2,2,2-trichloroethyl and pentafiuoroethyl;
Similarly, "alkoxy" and "alkylthio" refer to straight-chain or branched alkyl groups having
1 to 10 carbon atoms (as mentioned above) bonded through oxygen or sulfur linkages,
respectively, at any bond in the alky! group. Examples include inethoxy, ethoxy, pro-
poxy, isopropoxy, methylthio, ethyithio, propyltnio, isopropylthio, and n-butylthio.
Similarly, "alkylamino" refers to a nitrogen atom which carries 1 or 2 straight-chain or
branched alkyl groups having 1 to 10 carbon atoms (as mentioned above) which may
be the same or different. Examples include methylamino, dimethyiamino, ethylamino,
diethyiamino, methyiethylamino, isopropylamlno, or methyiisopropyiamino.
Similarly, "alkyisulfinyl" and "alkyfsulfonyj" refer to straight-chain or branched aikyl
groups having 1 to 10 carbon atoms (as mentioned above) bonded through -S(=0)- or
-S(=0)2-iinkages, respectively, at any bond in the alky! group. Examples include me-
thylsulfinyl and methyisulfonyl.
The term "alkyicarbonyl" refers to straight-chain or branched alkyl groups having i to
10 carbon atoms (as mentioned above) bonded through a -C(=0)- iinkage, respec-
tively, at any bond in the alkyl group. Examples include acetyl, propionyl, buturyl, or 2-
methylbuturyi.
The term "atkeny!" as used herein intends a branched or unbranched unsaturated hy-
drocarbon group having 2 to 6 carbon atoms and a double bond in any position, such
asethenyl, 1-propenyl, 2-propeny!, 1-methyl-etheny!, 1-butenyl, 2-butenyl, 3-butenyl, 1-
methyl-1-propenyl, 2-methyl-1-propeny!, 1-methy[-2-propenyl, 2-methyl-2-propenyl; 1-
pentenyi, 2-pentenyi, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-
methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-buteny!, 3-methyl-2-butenyt, 1-methyl-
3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl~2-propenyl, 1,2-
dimethyM-propenyl, 1,2-dimethyl-2-propenyJ, 1-ethyl-l-propenyl, 1-ethyl-2-propenyi, 1-
hexenyl, 2-hexenyl, 3-hexeny!, 4-hexenyl, 5-hexenyl, 1-methyM-pentenyl, 2-methyl-1-
penteny!, 3-methyl-1-pentenyl, 4-methyl-l-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-
pentenyl, 3-methyl-2-pentenyl, 4-methyt-2-pentenyl, 1-methyS-3-pentenyi, 2-methyl-3-
pentenyl, 3-methy!-3-pentenyI, 4-methyS-3-penteny!, l-methyl-4-pentenyl, 2-methy!-4-
pentenyl, 3-methyi-4-pentenyi, 4-methy!-4-pentenyl, 1,1-dimethyl-2-buteny!, 1,1-
dimethyl-3-butenyl, 1,2-dimeihyI-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-
butenyl, 1,3-dimethyM-butenyI, 1,3-dimethy!-2-butenyl, 1,3-dimethyl-3-butenyi, 2,2-
dimethyl-3-butenyl, 2,3-dimethyl-1-buteny!, 2,3-dimethy!-2-butenyl, 2,3-dimethyl-3-
butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-buteny!, 1 -ethyl- 1-butenyl, 1-ethyl-2-

14
butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyi-2-butenyl, 2-ethyl-3-bufenyl, 1,1,2-
trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyi-1-propenyland 1-
ethyl-2-methy!-2-propenyl;
The term "alkynyl" as used herein refers to a branched or unbrancbed unsaturated hy-
drocarbon group containing at least one triple bond, such as ethynyl, propynyl, 1-
butynyl, 2-butynyt, and the like.
A saturated, partially unsaturated or unsaturated 3- to 8-membered ring system which
contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur, is a ring system
wherein two oxygen atoms must not be in adjacent positions and wherein at ieast 1
carbon atom must be in the ring system e.g. thiophen, furan, pyrrol, thiazol, oxazol,
imidazo!, Isothlazoi, Isoxazol, pyrazoi, 1,3,4-oxadiazoi, 1,3,4-t.hiadiazol, 1.3,4-friazoS,
1,2,4-oxadiazoi,.1,2,4-th!adlazoi, 1,2,4-triazol, 1l2,3-triazo!,.1l2t3I4-tetrazo!, ben-
zo[b]thiophen, benzo[b]furan, indol, benzo[c]thiophen, benzo[c]furan, isoindol, ben-
zoxazo!, benzofhiazoi, benzimidazoi, benzisoxazoi, benzisotniazol, benzopyrazo!, ben-
zothiadiazoi, benzotriazol, dibenzofuran, dibenzothiophen, carbazol, pyridin, pyrazin,
pyrimidin, pyridazin, 1,3,5-triazin, 1,2,4-triazin, 1,2,4,5-tetrazin, chinolin, isochinolin,
chinoxalin, chinazolin, cinnoiin, 1,8-naphthyridin, 1,5-naphthyridin, 1,6-naphthyridin,
1,7-naphthyridin, phthalazin, pyridopyrimidin, purin, pteridin, 4H-chinoiizin, piperidin,
pyrroiidin, oxazolin, tetrahydrofuran, tetrahydropyran, isoxazolidin or thiazolidin.
A saturated, partially unsaturated or unsaturated 3- to 8-membered ring system which
contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur also is e.g.
a saturated, partially unsaturated or unsaturated 5-or 6-membered heterocyde which
contains 1 to 4 heteroatoms selected from oxygen, nitrogen and sulfur, such as pyri-
dine, pyrimidine, {1,2,4)-oxadiazole, (1,3,4)-oxadiazole, pyrrole, furan, thiophene, oxa-
zole, thiazole, imidazole, pyrazoie, isoxazole, 1,2,4-triazole, tetrazole, pyrazine, pyri-
dazine, oxazoline, thiazoline, tetrahydrofuran, tetrahydropyran, morpholine, piperidine,
piperazine, pyrroline, pyrrolidine, oxazolidine, thiazolidine, oxirane or oxetane ; or
a saturated, partially unsaturated or unsaturated 5-or 6-membered heterocyde which
contains 1 nitrogen atom and 0 to 2 further heteroatoms selected from oxygen, nitrogen
and sulfur, preferably from oxygen and nitrogen, such as piperidine, piperazin and
morpholine.
Preferably, this ring system is a saturated, partially unsaturated or unsaturated 3- to 6-
membered ring system which contains 1 to 4 heteroatoms selected from oxygen, nitro-
gen, sulfur, wherein two oxygen atoms must not be to adjacent positions and wherein
at least 1 carbon atom must be in the ring system.

15
Most preferably, this ring system is a radical of pyridine, pyrimidine, (1,2,4)-oxadiazol,
1,3,4-oxadiazoi, pyrrol, furan, thiophen, oxazo!, thiazol, imidazoi, pyrazoi, isoxazol,
1,2,4-triazol, tetrazol, pyrazin, pyridaz'm, oxazolin, thiazolin, tetrahydrofuran, tetrahy-
dropyran, morpholin, piperidin, piperazin, pyrroliri, pyrrolidin, oxazolidin, thiazolidin,
oxiran or oxetan.
Tn(Ci-Cio)a!kyisilyi refers to a silicon atom having 3 straight-chairvor branched C1-C10-
alkyi groups as defined above which may be the same or different. Examples include
trimethylsi!yi, triethylsilyl, triphenylsilyl or triisopropyisiiy!.
Cycloalky!: monocyclic 3- to 6-, or 8-membered saturated carbon atom rings, e.g. C3-
Cs-cycioaikyi such as cyciopropyl, cydobutyl, cyciopenty!, cyclohexyl, cycloheptyl, or
-cycloocfyl.
With respect to the Intended use of the compounds of formula i, particular preference is
given to the following meanings of the substituents, in each case on their own or in
combination:
A compound of formula I wherein R1 is hydrogen, CrCe-alkyl, cyano, C-i-Ce-
atkylsulfonyl, or C2-C6-alkoxycarbonyl, preferably hydrogen or Ci-C4-alkyl, most pref-
erably hydrogen.
A compound of formula I wherein A is A1.
A compound of formula I wherein A is A2.
A compound of formula I wherein R2 and R3 each independently are R6, -C{=0)R7, -
C(=NOR7)R7, -C{=NNR72)R7 , -C(=0)OR7, -C(=0)NR72, -OC(=0) R7, -OC(=0)OR7,
C(=0)NR7-NR72, -C(=0)NR7-NR7[C(=0)R7], or R2 and R3 together with the sulfur atom
to which they are attached form a' saturated, partially unsaturated or unsaturated 3- to
8-membered ring which contains 1 to 4 heteroatoms selected from oxygen, nitrogen,
sulfur, which ring can be fused with one or two saturated, partially unsaturated or un-
saturated 5- to 6-membered rings which may contain 1 to 4 heteroatoms selected from
oxygen, nitrogen, sulfur, wherein all of the above rings are unsubstituted or substituted
by any combination of 1 to 6 groups Rs.
More preferably, R2 and R3 each independently are RB or R2 and R3 together with the
sulfur atom to which they are attached form a saturated, partially unsaturated or un-
saturated 3- to 8-membered ring which contains 1 to 4 heteroatoms selected from oxy-
gen, nitrogen, sulfur, which ring can be fused with one or two saturated, partially un-
saturated or unsaturated 5- to 6-membered rings which may contain 1 to 4 heteroa-

16
toms selected from oxygen, nitrogen, sulfur, wherein all of the above rings are unsub-
stituted or substituted by any combination of 1 to 6 groups R8.
Even more preferred are compounds of formula I wherein R2 and R3.each independ-
ently are R6, preferably hydrogen, C-i-C2o-alkyl, C2-C2o-aikenyl, C2-C2o-aikynyl1 C3-C8-
cycloalkyl, C3-Cs-cycloalkenyl, C3-C8-cycloalkynyl, phenyl, naphthyl, biphenyi, or a
saturated, partially unsaturated or unsaturated 3- to 8-membered ring which contains 1
to 4 heteroatoms selected from oxygen, nitrogen, sulfur, wherein all of these groups
are unsubstituted or substituted by any combination of 1 to 6 groups R9.
Especially preferred are compounds of formula i wherein R2 and R3 each independ-
ently 3re Ci-Cio-alkyt, C2-Cio-aikenyl, C2-C-l0-a!kyny!i Ca-Cs-cycloalkyi, or phenyl,
wherein these groups are unsubstiiuted or substituted by any combination of 1 to 6
groups selected from R10or R11, and
R10 is Ci-do-aikyi, Cs-Cs-cycloalkyi, Ci-Cio-aIkyI-C3-Ca-cycloaIkyl or
a saturated, partially unsaturated or unsaturated 3- to 8-membered ring which contains
1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur, wherein these groups are
unsubstituted or substituted with any combination of from 1 to 6 groups R11, and
R11 is halogen; cyano, nitro, hydroxy, mercapto, amino, formyl, Ci-Cio-alkylcarbonyl,
Ci-Cio-alkoxy, Cz-Cw-alkenyloxy, C2-Cio-alkynyloxy, CrCio-haloa!koxy, Cs-Ce-
cycloaSkoxy, C3-Ce-halocycloaikoxy, Ci-Cio-alkoxycarbonyl, C3-CB-cycloaikoxycarbonyl,
Ci-Cio-a!ky!carbonyloxy, C3-Cs-cyclo alkylcarbonyioxy, Cr'Cio-haloalkoxycarbonyl, Ci-
Cio-ha!oa!kylcarbonyioxy, d-Cio-alkanamido, C3-C8-cycIoa]kanamido, Ci-Cio-alkylthio,
C2-Cio-alkenylthio, C2-C10-alkynylthio, Ci-Cio-haloa!kylthio, Ca-Ca-cycloalkylthio, C3-CS-
halocycloalkylthio, C3-Ce-cycloaikyl-C-i-C4-alkyithio, d-Cio-alkylsulfinyi, C2-C10-
aikenyisulfinyl, C2-Cio-alkynylsulfinyl, Ci-Cio-haloalkylsulfinyl, C3-C8-cycloalky!sulfinyi,
C3-Cs-haIocydoalkenylsulfinyl, C3-Ce-cycJoalkyl-Ci-C4-alkylsuifinyf, d-Cio-alkylsulfonyl,
C2-Cio-alkenyIsulfonyl, CrCto-alkynyfsulfonyl, C-i-Cio-haloalkyisuifonyi, C3-CB-
cycloalkyisulfonyl, Cs-Cs-halocycioalkylsulfonyl, C3-C8-cycloalkyl-C-i-C4-alkylsuifonyl,
di(Ci-Cio-alkyI)amino, CrCio-alkylamino, C2-C1o-alkenylamino, C2-Cio-alkyny!amino,
Ci-Cio-a!kyl-C2-Cio-alkenylamino, Ci-Cio-alkyl-C2-Cio-alkynylamino, C1-C10-
haloalkyfamino, C2-Cio-haioaikenylamino, C3-Ca-cycioalkylamino, tri(Ci-Cio-aIkyi)siiyi,
aryl, aryloxy, aryithio, arylamino, wherein aryl is phenyl, naphthyl or biphenyi, or
a saturated, partially unsaturated or unsaturated 3- to 8-membered ring system which
contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur,
wherein these ary! and these heterocyclic ringsystems are unsubstituted or substituted
with any combination of from 1 to 6 groups selected from halogen, cyano, nitro, amino,
hydroxy, mercapto, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-aikoxy, Ci-C4-haIoalkoxy, C1-C4-
alkylthio, Ci-Grhaloalkyithio, df(Ci-C4-alkyl) amino and Ci-C4-alkylamino.

17
More preferred are compounds of formula i wherein R2 and R3 each independently are
CrCio-aikyl1"'C2-Cio-a]kenyl, d-do-alkynyl, C3-Cs-cyc!oafky!, or phenyl, wherein these
groups are unsubstituted or substituted by any combination of 1 to 6 groups selected
from R11, and
R11 is halogen, cyano, nitro, hydroxy, mercapto, amino, d-do-alkoxy, d-do-
haioalkoxy, Crdrcycioaikoxy, d-do-alkoxycarbonyl, d-do-alky!carbony!oxy, d-do-
alkanamido, d-do-aikyitnio, d-do-alkylsu!finy!, d-do-a!ky[sulfonyL dt(d-do-
aiky!)amino or d-da-alkylarnino.
Preferred are also compounds of formula ! wherein R2 and R3 together with the sulfur
atom to which they are attached form a 5- or 6-rnernbered heterocyde which besides
the sulfur atom contains 1 nitrogen or 1 oxygen atom, wherein these groups are un-
substituted or substituted by any combination of 1 to 6 groups selected from with any
combination of from 1 to 6 groups selected from halogen, cyano, nitro, amino, hydroxy,
mercapto, d-d-alkyl, d-d-haloalkyi, d-d-alkoxy, d-C4-hafoalkoxy, d-d-alkyithio,
d-d-haloaikylthio, di(Ci-C4-a!kyl) amino and d-d-alkylamino.
Preferred are also compounds of formula I wherein R2 and R3 together with the sulfur
atom to which they are attached form a unit SR2R3 of the following formula:

wherein
r is 0 or 1 ;
D is a direct bond, branched or straight d-d-alkylene, 0, S(O)0,i,2 or NRi, prefera-
bly CH2l O, or NRi;
R9 is as defined above for compounds of formula I;
Ri is hydrogen, d-d-alky!, d-d-alkyicarbonyl, d-d-alkoxycarbonyl, d-d-
alkylaminocarbonyl, di(d-d-aiky])aminocarbonyl, or d-d-alkylsu!fonyl;
a,b are the same or different 0,1, 2, 3 or 4, preferably 0, 1, or 2.
When r = 0 then the both arylgroups are unbridged.
Preferred are compounds of formula I wherein R9 is R10, R11, or-C(=0)R1°, -
C(=NOR10)R10, -C(=NNR102)R10, -C(=0)OR™, -C(=O)NR102, -C(=O)NR10-NR102) -
C(=O)NR1°-NR10[C(=O)R10], -SO2NR102, -OR10, -NR102, or -SR10.
Preferred are compounds of formula 1 wherein R4 is NR12R13 and
R12and R13 are each independently hydrogen, d-C2o-aiky!, d-do-alkenyl or C2-C20-
alkynyl, each of which is unsubstituted or substituted by from 1 to 6 groups selected
from d-d-alkoxy, d-d-alkyithio, CN, HO2, formyl, d-d-aikylcarbonyl, d-d-

18
atkoxycarbonyt, d-d-aikylaminocarbonyl, di(d-d-alkyl)aminocarbonyi, d-d-
aikyisuifinyl, d-d-alkylsulfonyl, C3-C8-cycloalky!, and phenyl, wherein phenyl itself is
unsubstituted or substituted by 1 to 4 substituents selected from halogen, d-d-aikyl,
d-d-alkoxy, d-d-fluoroalkyl, d-d-alkyloxycarbonyl, trifluoromethylsulfonyl, formyl,
nitro and cyano; or
Ci-C2o-haloalkyl, C2-do-haloalkenyl, C2-C20-ha]oa!kyny!1 d-do-cycloalkenyl, or a satu-
rated or partially unsaturated or unsaturated 3~ to 8-membered ring system which con-
tains 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur, wherein this ring sys-
tem is unsubstituted or substituted by 1 to 4 substituents selected from halogen, C1-C4-
a!ky!: Ci-C4-a!koxy, d-d-fluoroalkyi, Cvd-aikyioxycarbonyi, trifluoromethylsulfonyl,
formyl, nitro and cyano; or
. R12 and R13 together with the .nitrogen atom to which they are attached may also form a
saturated or partially unsaturated 5- to 8-membered heterocycle which besides the one
nitrogen atom contains 0 to 2 further heteroatoms selected from oxygen, nitrogen, sul-
fur and may contain 1 or 2 carbonyl groups or thiocarbonyl groups and which is unsub-
stituted or substituted by from 1 to 4 groups selected from Ci-C4-a!kyl, d-d-alkoxy
and CrC4-haloatkyi.
More preferred are compounds of formula I wherein R4is NR12R13 and
R12and R13 are each independently hydrogen, d-do-alkyl, C2-C2o-alkenyi or C2-C20-
alkyny!, each of which is unsubstituted or substituted by from 1 to 3 CN, C1-C20-
haloalkyl, or R12 and R13 together with the nitrogen atom to which they are attached
may also form a saturated or partially unsaturated 5- to 8-membered heterocycle which
besides the one nitrogen atom contains 0 to 2 further heteroatoms selected from
oxygen, nitrogen, sulfur, and may contain 1 or 2 carbonyl groups or thiocarbonyl
groups and which is unsubstituted or substituted by from 1 to 4 groups selected from
Ci-C4-aIkyl, d-di-alkoxy and Ci-C4-haloalky!.
Especially preferred are compounds of formula I wherein R4is NR12R13 and R12 and R13
together with the nitrogen atom to which they are attached are a saturated or partially
unsaturated 5- or 6-membered nitrogen heterocycle which may be substituted by from
1 to 4 groups selected from CrC4-alkyl, d-d-alkoxy and d-d-haloalkyl, in particular
2,5-dihydropyrrol-1-yl, 2,3-dihydropyrroM-yl, 1-pyrrolidinyl, 1-piperidinyl, 4-morpholinyl,
2-methylmorpholin-4-yl, 2,6-dimethylmorphoiin-4-y!, or 1-methyipiperazin-4-yl.
Preferred are compounds of formula ! wherein R5 is hydrogen.
Preferred are compounds of formula I wherein Q1 is hydrogen, halogen, cyano, SCN,
nitro, hydroxy, d-do-alkyl, Crdo-haloalkyl, d-d-cycloalkyl, d-do-a)koxy, C1-C10-

19
haioalkoxy, Ci-CiG-alkylthio, Ci-Cio-haioalkylthio, Ci-Cio-alkylsuifonyl, C1-C10-
alkylsulfonyloxy, Ci-Cio-alkylamino or di(CrGio-aIky!)amino, most preferably hydrogen,
halogen, cyano, CrC4-alkyl or CrC4-ha!oalkyl.
Preferred are compounds of formula I wherein G2is halogen, cyano, SCN, nitro, hy-
droxy, Ci-Cio-alkyl, Ci-Cio-ha!oaikyl, C3-C8-cycloalkyl, Ci-Cio-alkoxy, C1-C10-
.haloaikdxy, CrCio-alkyithio, Ci-Cio~haioaiky!thio, Ci-Cic-aikyisulfonyi, CrCicr
alkylsulfonyloxy, CrCio-atkylamino or di(Ci-Cio-aikyl)amin"Q, most preferably halogen,
cyano, Ci-C4-a!kyl or Ci-C4-haloaikyi.
Preferred are compounds of formula I wherein Q3 is halogen, Ci-Cio-a!kyl, C1-C10-
haioalkyS, C2-Cio-a!ky-ny!, C-3-Cg-cyc-Soatky!, Cs-Cfi-haiocycloalkyl, each unsubstituted or
Independently substituted with 1 to 2 groups selected from cyano, Ci-Cio-alkoxy, C1-
Cio-haloalkoxy or CrCio-alkyithio, or
CPis ORH, S(0)qR14, NR15R16, OS(0)2R17, C(S)NH2, C(R1B)=NOR18; and
R14 is CrCio-alky! or Ca-Cs-cycioalkyl unsubstituted or substituted with 1 R19; and
R15 is d-Cio-alkyl, d-Cio-haloalkyl, C2-Cio-a[kenyl, C2-Cio-alkynyl, each unsubstituted
or substituted with 1 R1S; and
R16 is hydrogen, CrCio-a!ky!t Ci-Cio-haioalkyI, C2-Cio-alkeny!, C2-Cio-alkynyl, each
unsubstituted or substituted with 1 R19; and
R17 is Ci-Cio-alkyl, Ci-Cio-haloalkyi, C2-Cio-aikenyl, C2-Cio-alkynyl, Cs-Cs-cycloaikyl,
each unsubstituted or substituted with 1 R19; and
R1B is hydrogen, Ci-Cio-alkyl, or Ci-Cio-ha!oaikyl; and
R19 is cyano, nitro, Ci-Cio-alkoxy, d-Cio-haloalkoxy, Ci-Cio-alkyithio, or C1-C10-
haloalkylthio.
Most preferred are compounds of formula I wherein Q3 is halogen, Ci-C-v-haioalkyI or
CrC4-haioalkoxy.
Preferred are compounds of formula I wherein Q4 is halogen, cyano, nitro, Ci-Cio-alkyl,
Ci-Cio-haloalkyi, Ci-Cio-alkoxy, Ci-Cio-haloalkoxy, Ci-Cio-alkytthio, C1-C10-
haloalkylthio, CrCio-alkylsulfinyl, Ci-Cio-hatoalkylsuIfinyl, CVCio-aikyisuffonyl, C1-C10-
haloalkylsulfonyf, or Ci-Cio-alkoxycarbonyl, preferably halogen or Ci-d-haloalkyl.
Preferred are compounds of formula I wherein X and Y are oxygen.

20
Preferred are compounds of formula I wherein W is N or CQ4, preferably N.
Preferred are compounds of formula I wherein m is 2.
Preferred are compounds of formula 1 wherein n is 0,
Preferred are compounds of formula i wherein V and V each independently are N or
CH. Preferably, both V and V are CH.
Especially preferred are N-thio-anthranilamid compounds of formula \ wherein
w !Q N-
R1 is hydrogen;
Q1 Is hydrogen, halogen, cyano, Ci-C4-aikyi or CrC4-haioa!ky!;
Q2. Is.halogen, cyano, Ci-CU-alky! or;d-Ci-haloalkyl;
Q3 is halogen, CrC4-haloalkyl or Ci-C4-haloalkoxy;
Q4 is halogen or Ci-C4-ha!oafkyl and is in the ortho-position; and
p is 1.
Also, especially preferred are N-thio-anthranilamid compounds of formula I wherein
A is A2;
R4 is Ci-CG-alkylamino, C2-C6-alkeny!amino, Cz-Cs-alkynylamino, di(Ci-C6-
alkyi)amino, di{C2-C6-alkenyl)amino, di(C2-C6-alkynyl)amino, (phenyi)(Ci-C6-
alkyI)amino, (phenyl)(C2-C6-aikenyl)amino, (phenyl)(C2-C6-alkyny[)amino,
piperidine, piperazin or morpholine; and
R5 is hydrogen or d-C4-aIkyl.
Also, especially preferred are N-thio-anthranilamtd compounds of formula i wherein
A is A1; and
R2and R3 each independently are phenyl, CrCe-alkyl, C2-C6-alkeny!, or C2-Ce-alkynyl,
which are unsubstituted or substituted with any combination of 1 to 6 groups se-
lected from halogen and cyano.
Most preferred are compounds of formula I wherein R2 and R3 each independently are
CrC4-a!ky!, phenylmethyi, allylmethyl, propargylmethyl, or together with the sulfur
atom to which they are attached form a 3- to 6-membered saturated ring which con-
tains 1 to 3 heteroatoms selected from sulfur and oxygen.
With respect to their use, particular preference is given to the compounds (A compiled
in the tables below. Moreover, the groups mentioned for a substituent in the tables are
on their own, independently of the combination in which they are mentioned, a particu-
larly preferred embodiment of the substituent in question.

21
Table 1
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CF3, and A in
each case corresponds to a row of Table A.

I Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes bromine, and
A In each case corresponds to a row of Table A,
Table 3
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes chlorine, and
A in each case corresponds to a row of Table A.
Table 4
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH3, and A in
each case corresponds to a row of Table A.
Table 5
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH3, and A
in each case corresponds to a row of Table A.
Table 6
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCHCH2, and
A in each case corresponds to a row of Table A.
Table 7
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes ethoxy, and A
in each case corresponds to a row of Table A.
Table 8
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
OCH2CHFOCH3, and A in each case corresponds to a row of Table A.
Table 9
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
OCH2CH=CH2, and A in each case corresponds to a row of Table A.
Table 10

22
Compounds of the formula iA wherein Q1 denotes hydrogen, Q3 denotes OCH2CCH,
and A in each case corresponds to a row of Table A.
Table 11
Compounds of the formula iA wherein Q1 denotes hydrogen, Q3 denotes CH2OCH3,
and A in each case corresponds to a row of Table A.
Table 12
Compounds of the formula !A wherein Q1 denotes hydrogen, Q3 denotes
CH2OCH2CH3, and A in each case corresponds to a row of Tabie A.
Table 13
Compounds of the formula !A wherein Q1 denotes hydrogen, Q3 denotes CiSChb,
and A In each case corresponds to a row of Tab's A.
Table 14
Compounds of the formula IA wherein G1 denotes hydrogen, Q3 denotes CH2SCH2CH3,
and. A in each case corresponds to a row of Table A.
Table 15
Compounds of the formuia IA wherein Q1 denotes hydrogen, Q3 denotes
CH2S(=0)CH3, and A in each case corresponds to a row of Table A.
Tabie 16
Compounds of the formuia IA wherein Q1 denotes hydrogen, Q3 denotes
CH2S(=0)CH2CH3, and A in each case corresponds to a row of Table A.
Table 17
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
CH2S(=0)2CH3, and A in each case corresponds to a row of Table A.
Table 18
Compounds of the formula 1A wherein Q1 denotes hydrogen, Q3 denotes
CH2S(=0)2CH2CH3! and A in each case corresponds to a row of Table A.
Table 19
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes -OS(=0)2CH3,
and A in each case corresponds to a row of Table A,
Table 20
Compounds of the formuia !A wherein Q* denotes hydrogen, Q3 denotes
-OS(=0)2CH2CH3, and A in each case corresponds to a row of Table A.

23
Table 21
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
-OS(=0)2CH2CF3, and A in each case corresponds to a row of Table A.
Table 22
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
-OS(=0)2GC!F2, and A in each case corresponds to a row of Table A.
Table 23
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OC(=0)CF3,
and A In each case corresponds to a row of Table A.
Table 24
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes NHCHzCFa,
and A in each case corresponds to a row of Table A.
Table 25
Compounds of the formula IA wherein Q1 denotes hydrogen, G3 denotes
OChb-cyclopropy!, and A in each case corresponds to a row of Table A.
Table 26
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
OCH2C(CI)=CH2, and A in each case corresponds to a row of Table A,
Table 27
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
OCH2CH=CF2, and A in each case corresponds to a row of Table A.
Tabfe28f
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
NHS(=0)2CF3, and A in each case corresponds to a row of Table A.
Table 29
Compounds of the formula [A wherein Q1 denotes hydrogen, Q3 denotes NHC(=0}CF3,
and A in each case corresponds to a row of Table A.
Table 30
Compounds of the formula SA wherein Q1 denotes hydrogen, Q3 denotes OCH2CN, and
A in each case corresponds to a row of Table A.
Table 31

24
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH2N02,
and A in each case corresponds to a row of Table A.
Table 32
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes cyciopropy-
ioxy, and A in each case corresponds to a row of Table A.
Table 33
Compounds of the formula !A wherein Q1 denotes hydrogen, Q3 denotes ChbQCHF?,
and A in each case corresponds to a.row of Table A.
Table 34
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
Gn2S(=G}2CHF2rand A in each.case corresponds to a row of Table A.
Table 35
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH=NOCH3,
and A in each case'corresponds to a row of Table A.
Table 36
Compounds of the formula f A wherein Q1 denotes hydrogen, Q3 denotes
CH=NOCH2CH3, and A in each case corresponds to a row of Table A.
Table 37
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
CH=NOCH(CH3)2and A in each case corresponds to a row of Table A.
Table 38
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
CH=NOC(CH3)3, and A in each case corresponds to a row of Table A.
Table 39
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
C(CH3)=NOCH3, and A in each case corresponds to a row of Table A.
Table 40
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
C(CH3)=NOCH2CH3, and A in each case corresponds to a row of Table A.
Table 41
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
C(CH3}=NOCH(CH3)2, and A in each case corresponds to a row of Table A.

25
Table 42
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
C(CH3)=NOC(CH3)3, and A in each case corresponds to a row of Table A.
Table 43
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CF3, and A in
each case corresponds to a row of Table A.
T-Klci AA
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes bromine, and A
IT! BcSULS sjctSB uunciUi lus lu a luvV Oi i aOiS A.
Table 45
Compounds of the formula iA wherein Q1 denotes chiorine, Q3 denotes chlorine, and A
in each case corresponds to a row of Table A.
Table 46
Compounds of the formula IA wherein Q1 denotes chiorine, Q3 denotes CHz, and A in
each case corresponds to a row of Table A.
Table 47
Compounds of the formula iA wherein Q1 denotes chiorine, Q3 denotes OCH3, and A in
each case corresponds to a row of Table A.
Table 48
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCHCH2, and
A in each case corresponds to a row of Table A.
Table 49
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes ethoxy, and A
in each case corresponds to a row of Table A.
Table 50
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
OCH2CHFOCH3, and A in each case corresponds to a row of Table A,
Table 51
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2CH=CH2,
and A in each case corresponds to a row of Table A,
Table 52

26
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2CCH, and
A in each case corresponds to a row of Table A.
Table 53
Compounds of the'formula !A wherein Q1 denotes chlorine, Q3 denotes CH2OCH3, and
A in each case corresponds to a row of Table A.
Table 54
Compounds of the formula iA wherein Q1 denotes chlorine, G3 denotes CH2OCH2CH3,
and A. \n each case corresponds to a row of Table A.
Tabie 55
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2SCH3, and
A in each case corresponds to a row of Table A.
Table 56
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2SCH2CH3,
and A in each case corresponds to a row of Table A.
Table 57
Compounds of the formula (A wherein Q1 denotes chlorine, Q3 denotes CH2S(=0)CH3,
and A in each case corresponds to a row of Table A.
Tabie 58
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
CH2S(=0)CH2CH3, and A in each case corresponds to a row of Table A.
Table 59
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2S(=0)2CH3,
and A in each case corresponds to a row of Table A.
Table 60
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
CH2S(=0)2CH2CH3, and A in each case corresponds to a row of Table A.
Table 61
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes -OS(=0)2CH3,
and A in each case corresponds to a row of Table A.
Table 62
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
-0S(=O)2CH2CH3, and A in each case corresponds to a row of Table A.

27
Table 63
Compounds of the formula JA wherein Q1 denotes chiorine, Q3 denotes
-OS(=0)2CH2CF3, and A in each case corresponds to a row of Table A.
Table 64
Compounds of the formula !A wherein Q1 .denotes chlorine, Q3 denotes
-0S(=O)2GCip2, and A in each case corresponds to a row of Table A.
Tabie 65
Compounds of the formula IA wherein Q1 denotes chiorine, Q3 denotes OC(-Q)CF3,
and A in each case corresponds to a row of Table A.
Table 65
Compounds of the formula IA wherein Q1 denotes chlorine, Q5 denotes MHCH2CF3,
and A in each case corresponds to a row of Table A.
Table 67
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
OChVcyclopropyl, and A in each case corresponds to a row of Table A,
Table 68
Compounds of the formula !A wherein Q1 denotes chiorine, Q3 denotes
OCH2C(CI)=CH2, and A in each case corresponds to a row of Table A.
Table 69
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2CH=CF2,
and A in each case corresponds to a row of Table A.
Tabie 70
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes NHS(=0)2CF3,
and A in each case corresponds to a row of Table A."
Table 71
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes NHC(=0)CF3,
and A in each case corresponds to a row of Table A.
Table 72,
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2CN, and
A in each case corresponds to a row of Tabie A.
Table 73

28
Compounds of the formula !A wherein Q1 denotes chlorine, G3 denotes OCH2NO2, and
A in each case corresponds to a row of Table A.
Table 74
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes cyciopropyloxy,
and A in each case corresponds to a row of Table A.
Table 75
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2OCHF2,
and A in each case corresponds to a row of Table A.
Table 76
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
CH2S(=0)2CHF2, and A in each case corresponds to a row of Table A.
Table 77
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH=NOCH3,
and A in each case corresponds to a row of Table A.
Table 78
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
CH=NOCH2CH3, and A in each case corresponds to a row of Table A.
Table 79
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
CH=NOCH(CH3)2 and A in each case corresponds to a row of Table A.
Table 80
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
CH=NOC(CH3)3, and A in each case corresponds to a row of Table A.
Table 81
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
C(CH3)=NOCH3l and A in each case corresponds to a row of Table A.
Table 82
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
C(CH3)=NOCH2CH3, and A in each case corresponds to a row of Table A.
Table 83
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
C(CH3)=NOCH(CH3)2, and A in each case corresponds to a row of Table A.

29
Table 84
Compounds of the formula 1A wherein Q1 denotes chlorine, Q3 denotes
C(CH3)=NOC(CH3)3, and A in each case corresponds to a row of Table A.
Table 85
Compounds of the formula !A wherein Q1 denotes bromine, Q3 denotes CF3, and A in
each case corresponds to a row of Table A,
Table 86
Compounds of the formula lA wherein Q1 denotes bromine, Q3 denotes bromine, and A
in each case corresponds to a row of Table A,
Table 87
Compounds of the formula iA wherein Q1 denotes bromine, Q3 denotes chlorine, and A
in each case corresponds to a row of Table A.
Table 88
Compounds of the formula (A wherein Q1 denotes bromine, Q3 denotes CH3, and A in
each case corresponds to a row of Table A.
Table 89
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH3, and A in
each case corresponds to a row of Table A.
Table 90
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCHCH2, and
A in each case corresponds to a row of Table A.
Table 91
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes ethoxy, and A
in each case corresponds to a row of Tabfe A.
Table 92
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
OCH2CHFOCH3, and A in each case corresponds to a row of Table A.
Table 93
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2CH=CH2,
and A in each case corresponds to a row of Table A,
Table 94

30
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OChkCCH,
and A in each case corresponds to a row of Table A.
Table 95
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2OCH3, and
A in each case corresponds to a row of Table A.
Table 96
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2OCH2CH3,
and A in each case corresponds to a row of Table A.
Table 97
Compounds of the formula !A wherein Q1 denotes bromine, Q3 denotes CH2SCH3, and
A in each case corresponds to a row of Table A.
Table 93
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2SCH2CH3,
and A in each case corresponds to a row of Table A.
Table 99
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2S(=0)CH3,
and A in each case corresponds to a row of Table A.
Table 100
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
CH2S(=0)CH2CH3, and A in each case corresponds to a row of Table A.
Table 101
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2S(=0)2CH3,
and A in each case corresponds to a row of Table A.
Table 102
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
CH2S(=0)2CH2CH3, and A In each case corresponds to a row of Table A.
Table 103
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes -OS(=0)2CH3,
and A in each case corresponds to a row of Table A.
Table 104
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
-OS(=0)2CH2CH3, and A in each case corresponds to a row of Table A.

31
Table 105
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
-0S(=O}2CH2CF3! and A in each case corresponds to a row of Table A.
Table 106
Compounds of the formula (A wherein Q1 denotes bromine, Q3 denotes
-OSOCCIFo, and A in each case corresponds to a row of Table A.
Tabie 107
Compounds of the formula !A wherein Q1 denotes bromine, Q3 denotes OC(=0)CF3,
and A in each case corresponds to a row of Table A,
Table 108
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes NHC-H2CF3,
and A in each case corresponds to a row of Table A.
Table 109
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
OCH2-cyclopropyl, and A in each case corresponds to a row of Table A.
Table 110
Compounds of the formula iA wherein Q1 denotes bromine, Q3 denotes
OCH2C(C!):=CH2, and A in each case corresponds to a row of Table A,
Tabie 111
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2CH=CF2,
and A in each case corresponds to a row of Table A.
Table 112
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes NHS(=0)2CF3,
and A in each case corresponds to a row of Table A.
Table 113
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes NHC(=0)CF3,
and A in each case corresponds to a row of Table A.
Table 114
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2CN, and
A in each case corresponds to a row of Table A.
Table 115

32
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2N02s and
A in each case corresponds to a row of Table A.
Table 116
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes cyclopropyloxy,
and A in each case corresponds to a row of Table A,
Table 117 '
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2OCHF2,
and A in each case corresponds to a row of Table A.
Table 118
Compounds of the formula IA wherein Q1 denotes bromine, v* usnotss
GH2S(=G)2GHF2, and A in each case corresponds to a rovv.or.! able.A.
Table 119
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH=NOCH3,
and A in each case corresponds to a row of Table A.
Table 120
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
CH=NOCHsCH3, and A in each case corresponds to a row of Table A.
Table 121
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
CH=NOCH(CH3)2and A in each case corresponds to a row of Table A.
Table 122
Compounds of the formula !A wherein Q1 denotes bromine, Q3 denotes
CH=NOC(CH3)3, and A in each case corresponds to a row of Table A.
Table 123
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
C(CH3)=NOCH3, and A in each case corresponds to a row of Table A.
Table 124
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
C(CH3)=NOCH2CH3, and A in each case corresponds to a row of Table A.
Table 125
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
C(CH3)=NOCH(CH3)2, and A in each case corresponds to a row of Table A.

33
Table 126
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
C(CH3)=NOC(CH3)3, and A in each case corresponds to a row of Table A.
Table 127
Compounds of the formula iA wherein Q' denotes fluorine, Q3 denotes CF3, and A in
each case corresponds to a row of Table A,
Table 128
Compounds of the formula !A wherein Q1 denotes fluorine, Q3 denotes bromine, and A
in each case corresponds to a row of Table A.
Table 129
Compounds of the formuia iA wherein Q1 denotes fluorine, Gr denotes chlorine, and A
in each case corresponds to a row of Table A.
Tabie 130
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH3, and A in
each case corresponds to a row of Tabie A.
Table 131
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH3, and A in
each case corresponds to a row of Table A,
Table 132
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCHCH2, and A
in each case corresponds to a row of Table A.
Table 133
Compounds of the formula f A wherein Q1 denotes fluorine, Q3 denotes ethoxy, and A in
each case corresponds to a row of Table A.
Table 134
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
OCH2CHFOCH3, and A in each case corresponds to a row of Table A.
Table 135
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH2CH=CH2,
and A in each case corresponds to a row of Table A.
Table 136

34
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH2CCH, and
A in each case corresponds to a row of Tabie A.
Table 137.
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2OCH3, and
A in each case corresponds to a row of Tabie A.
Table 138
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2OCH2CH3,
and A in each case corresponds to a row of Table A,
Table 133
r'.rimnoLind" rvf fhp forms iia !A u.'herp.in O1 ri(=»nnfp A in earrh caS GOTAnrind* to a rrw/ rif TSNP A
Table 140
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2SCH2CH3,
and A in each case corresponds to a row of Table A.
Table 141
Compounds of the formula iA wherein Q1 denotes fluorine, Q3 denotes CH2S(=0)CH3,
and A in each case corresponds to a row of Table A.
Tabie 142
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
CH2S(=0)CH2CH3, and A in each case corresponds to a row of Table A.
Table 143
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2S(=0)2CH3,
and A in each case corresponds to a row of Table A.
Table 144
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
CH2S(=0)2CH2CH3, and A In each case corresponds to a row of Table A.
Table 145
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes -OS(=0)2CH3,
and A in each case corresponds to a row of Table A.
Table 146
Compounds of the formula !A wherein Q1 denotes fluorine, Q3 denotes
-OS(=0)2CH2CH3, and A in each case corresponds to a row of Table A.

35
Table 147
Compounds of the formula 1A wherein Q1 denotes fluorine, Q3 denotes
-0$(=0)2CH2CF3, and A in each case corresponds to a row of Table A.
Table 148
Compounds of the formula 1A wherein Q1 denotes fluorine, Q3 denotes -OSO-QCCiF?,
and A in each case corresponds to a row of Table A,
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OC(=0)CF3,
and A in each case corresponds to a row of Tabie A.
Table 150
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes NHCH2CF3, and
A in each case corresponds to a row of Table A.
Table 151
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
OCH2-cyc!opropyi, and A in each case corresponds to a row of Table A.
Table 152
Compounds of the formula JA wherein Q1 denotes fluorine, Q3 denotes
OCH2C(Ci)=CH2, and A in each case corresponds to a row of Table A.
Table 153
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH2CFNCF2,
and A in each case corresponds to a row of Table A.
Table 154
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes NHS(=0)2CF3,
and A in each case corresponds to a row of Table A,
Table 155
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes NHC(=0)CF3,
and A in each case corresponds to a row of Table A.
Table 156
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH2CN, and A
in each case corresponds to a row of Table A.
Table 157

36
Compounds of the formula SA wherein Q1 denotes fluorine, Q3 denotes OCH2NO2, and
A in each case corresponds to a row of Table A.
Table 158
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes cyclopropyloxy,
and A in each case corresponds to a row of Table A.
Table 159
Compounds of the formula !A wherein Q1 denotes fluorine, Q3 denotes CH2OCHF2, and
A in each case corresponds to a row of Table A.
Table 160
Compounds of the formula iA wherein Q1 denotes fluorine, Q3 denotes
CH2S(=0)2C.HF2, and A in each case corresponds to a row of Table A.
Table 161
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH=NOCH3,
and A in each case corresponds to a row of Table A.
Table 162
Compounds of the formula iA wherein Q1 denotes fluorine, Q3 denotes
CH=NOCH2CH3, and A in each case corresponds to a row of Table A.
Table 163
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
CH=NOCH(CH3)2 and A in each case corresponds to a row of Table A.
Table 164
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
CH-NOC(CH3)3, and A in each case corresponds to a row of Table A.
Table 165
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
C(CHs)=NOCH3, and A in each case corresponds to a row of Table A.
Table 166
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
C(CH3)=NOCH2CH3, and A in each case corresponds to a row of Table A.
Table 167
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
C(CH3)=NOCH(CH3)2, and A in each case corresponds to a row of Table A.

37
Table 168 '".-='"
Compounds of the formula lA wherein Q1 denotes fluorine, Q3 denotes
C(CH3)=NOC{CH3)3, and A in each case corresponds to a row of Table A.
Table 169
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CF3, and A in
each case corresponds to a row of Table A.
Table 170
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes bromine, and A in
each case corresponds to a row of Table A.
Table 171
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes chiorine, and A in
each case corresponds to a row of Table A.
Table 172
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH3, and A in
each case corresponds to a row of Table A.
Table 173
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH3, and A in
each case corresponds to a row of Table A.
Table 174
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCHCH2, and A
in each case corresponds to a row of Table A.
Table 175
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes ethoxy, and A in
each case corresponds to a row of Table A.
Table 176
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2CHFOCH3,
and A in each case corresponds to a row of Table A.
Table 177
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2CH=CH2,
and A in each case corresponds to a row of Table A.
Table 178

38
Compounds of the formula !A wherein Q1 denotes iodine, A in each case corresponds to a row of Table A.
Table 179
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2OCH3, and A
in each case corresponds to a row of Table A.
Table 180
Compounds of the formula sA wherein Q1 denotes iodine, Q3-denotes CH2OCH2CH3,
and A in each case corresponds to a row of Table A.
Table 181
Compounds of the formula IA wherein Q." denotes iodine Q3 denotes CriSuMs, anu A
.in each case corresponds to a row of Tabie A.
Table 182
Compounds of the formula !A wherein Q1 denotes iodine, Q3 denotes CH2SCH2CH3,
and A in each case corresponds to a row of Table A.
Table 183
Compounds of theformuia iA wherein Q1 denotes iodine, Q3 denotes CH2S(=0)CH3,
and A in each case corresponds to a row of Table A.
Table 184
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes
CH2S(=0)CH2CH3, and A in each case corresponds to a row of Table A.
Table 185
Compounds of theformuia IA wherein Q1 denotes iodine, Q3 denotes CH2S(=0)2CH3,
and A in each case corresponds to a row of Table A.
Table 186
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes
CH2S(=0)2CH2CH3, and A in each case corresponds to a row of Table A.
Table 187
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes -OS(=0)2CH3,
and A in each case corresponds to a row of Table A.
Table 188
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes
-OS(=0)2CH2CH3, and A in each ease corresponds to a row of Table A.

39
Table 189
Compounds of the formula IA wherein G1 denotes iodine, Q3 denotes
-OS{=0}2CH2CF3, and A in each case corresponds to a row of Table A.
Table 190
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes ~0S(=O)2CC!F2,
and A in each case corresponds to a row of Table A.
Tf-.la -!Q1
I WL/lC 1 1
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OC(=0)CF3, and
A in eacn case conresponus to a row of Table A.
Table 192
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes NHCH2CF3, and
A in each case corresponds to a row of Table A.
Table 193
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes
OCbh-cycSopropyl, and A in each case corresponds to a row of Table A,
Table 194
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2C(CI)=CH2,
and A in each case corresponds to a row of Table A.
Table 195
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2CH=CF2,
and A in each case corresponds to a row of Table A,
Table 196
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes NHS(=0}2CF3,
and A in each case corresponds to a row of Table A.
Table 197
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes NHC(=0)CF3,
and A in each case corresponds to a row of Table A.
Table 198
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2CN, and A
in each case corresponds to a row of Table A.
Table 199

40
Compounds of the formula 1A wherein Q1 denotes iodine, G3 denotes OCH2N02, and A-
in each case corresponds to a row of Table A.
Table 200
Compounds of the formuia IA wherein Q1 denotes iodine, G3 denotes cyclopropyloxy,
and A in each case corresponds to a row of Tabie A.
Table 201
Compounds of the formuia IA wherein Q1 denotes iodine, Q3 denotes CH2OCHF2, and
i\ jri each case corrssoonds to a row of Table A.
Table 202
Compounds of the formula !A wherein Q1 denotes Iodine, Q3 denotes CH2S(=0)2CHF2,
and A in. each case corresponds to a.row of Tabie A-
Table 203
Compounds of the formula !A wherein Q1 denotes iodine, Q3 denotes CH=NOCH3, and
A in each case corresponds to a row of Table A.
Table 204
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH=NOCH2CH3,
and A in each case corresponds to a row of Table A.
Tabie 205
Compounds of the formula [A wherein Q1 denotes iodine, Q3 denotes CH=NOCH(CH3)2
and A in each case corresponds to a row of Table A.
Table 206
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH=NOC(CH3)3,
and A in each case corresponds to a row of Table A.
Table 207
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes C(CH3)=NOCH3,
and A in each case corresponds to a row of Table A.
Tabie 208
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes
C(CH3)=NOCH2CH3, and A in each case corresponds to a row of Table A,
Table 209
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes
C{CH3)=NOCH(CH3)2, and A in each case corresponds to a row of Table A,

41
Table 210
Compounds of the formula IA wherein O1 denotes iodine, Q3 denotes
C(CH3}=NOC(CH3)3, and A in each case corresponds to a row of Table A.
Table 211
Compounds of the formula IA. wherein Q1 denotes cyano, Q3 denotes CF3, and A in
each case corresponds to a row of Table A.
Table 212
Compounds of the formula !A wherein Q1 denotes cyano, Q3 denotes bromine, and A in
each case corresponds to a row of Table A.
Table 213
Compounds of the formula iA wherein Q1 denotes cyano, Q3 denotes chlorine, and A in
each case corresponds to a row of Table A.
Table 214
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH3, and A in
each case corresponds to a row of Table A.
Table 215
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH3, and A in
each case corresponds to a row of Table A.
Table 216
Compounds of the formula iA wherein Q1 denotes cyano, Q3 denotes OCHCH2, and A
in each case corresponds to a row of Table A.
Table 217
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes ethoxy, and A in
each case corresponds to a row of Table A.
Table 218
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2CHFOCH3,
and A in each case corresponds to a row of Table A.
Table 219
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2CH=CH2,
and A in each case corresponds to a row of Table A.
Table 220

42
Compounds of the formula 1A wherein Q1 denotes cyano, Q3 denotes OCH2CCH, and
A in each case corresponds to a row of Table A.
Table 221 .
Compounds of the formula SA wherein Q1 denotes cyano, Q3 denotes CH2OCH3, and A
in each case corresponds to a row of Table A.
Table 222
Compounds of the formula !A wherein Q1 denotes cyano, Q3 denotes CH2OCH2CH3,
and A in each case corresponds to a row of Table A.
Table 223
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2SCH3, and A
ineach'casecdrfespdhdsloaroW'df'TabisA.
Table 224
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2SCH2CH3,
and A in each case corresponds to a row of Table A.
Table 225
Compounds of the formula iA wherein Q1 denotes cyano, Q3 denotes CH2S(=0)CH3,
and A in each case corresponds to a row of Table A,
Table 226
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes
CH2S(=0)CH2CH3, and A in each case corresponds to a row of Table A.
Table 227
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2S(=0)2CH3,
and A in each case corresponds to a row of Tabie A.
Table 228
Compounds of the formula SA wherein Q1 denotes cyano, Q3 denotes
CH2S(=0)2CH2CH3, and A in each case corresponds to a row of Table A.
Table 229
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes -OS(=0)2CH3,
and A in each case corresponds to a row of Table A.
Table 230
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes
-OS(=0)2CH2CH3, and A in each case corresponds to a row of Table A.

43
Table 231
Compounds of the formula lA wherein Q1 denotes cyano, G3 denotes
-OS(=0)2CH2CF3, and A in each case corresponds to a row of Table A.
Table 232
Compounds of the formula !A wherein Q1 denotes cyano, Q3 denotes -OB(~-0)2CC\Fz,
and A in each case corresponds to a row of Table A.
Table 233
Compounds of the formuia IA wherein Q'! denotes cyano, Q3 denotes OC(=0)CF3, and
A in each case corresponds to a row of Table A.
Table 234
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes NHCH2CF3, and
A in each case corresponds to a row of Table A.
Table 235
Compounds of the formula !A wherein Q1 denotes cyano, Q3 denotes
OCH2-cyciopropy!, and A in each case corresponds to a row of Table A.
Table 236
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2C(CI)=CH2,
and A in each case corresponds to a row of Table A.
Tabie 237
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2CH=CF2,
and A in each case corresponds to a row of Table A.
Table 238
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes NHS(=0)2CF3,
and A in each case corresponds to a row of Table A.
Table 239
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes NHC(=0)CF3,
and A in each case corresponds to a row of Table A.
Table 240
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2CN, and A
in each case corresponds to a row of Table A.
Table 241

44
Compounds of the formula 1A wherein Q1 denotes cyano, Q3 denotes OCH2N02, and A
in each case corresponds to a row of Table A.
Table 242
Compounds of the formula lA wherein Q1 denotes cyano, G3 denotes cyclopropyfoxy,
and A in each case corresponds to a row of Table A.
Table 243
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2OCHF2, and
A in each cass corresponds to a row of Table A,
Table 244
Compounds of the formula !A wherein Q1 denotes cyano, Q3 denotes CH2S(=0)2CHF2,
and A in each case corresponds to a row of Table A.
Table 245
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH=NOCH3, and
A in each case corresponds to a row of Table A.
Table 246
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH=NOCH2CH3,
and A in each case corresponds to a row of Table A.
Table 247
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH=NOCH(CH3)2
and A in each case corresponds to a row of Table A.
Table 248
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH=NOC(CH3)3,
and A in each case corresponds to a row of Table A.
Table 249
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes C(CH3)=NOCH3,
and A in each case corresponds to a row of Table A.
Table 250
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes
C(CH3)=NOCH2CH3, and A in each case corresponds to a row of Table A,
Table 251
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes
C(CH3)=NOCH(CH3)2, and A in each case corresponds to a row of Table A.

45
Table 252
Compounds of the formula 1A wherein Q1 denotes cyano, Q3 denotes
C(CH3)=NOC(CH3)3, and A in each case corresponds to a row of Tabie A.
Table 253
Compounds of the formula !A wherein Q1 denotes methyl, Q3 denotes CP3, and A in
each case corresponds to a row of Table A,
Table 254
Compounds of the formula lA wherein Q1 denotes methyi, Q3 denotes bromine, and A
in each case corresponds to a row of Tabie A.
Table 255
Compounds of the formula iA wherein Q1 denotes methyl, Q3 denotes chiorine, and A
in each case corresponds to a row of Table A.
Table 256
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH3, and A in
each case corresponds to a row of Table A.
Table 257
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH3, and A in
each case corresponds to a row of Table A,
Table 258
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCHCH2, and A
in each case corresponds to a row of Table A.
Table 259
Compounds of the formula IA wherein Q1 denotes methyi, Q3 denotes ethoxy, and A in
each case corresponds to a row of Table A,
Table 260
Compounds of the formula !A wherein Q1 denotes methyl, Q3 denotes OCH2CHFOCH3,
and A in each case corresponds to a row of Table A.
Table 261
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2CH=CH2,
and A in each case corresponds to a row of Table A.
Tabie 262

46
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2CCH, and
A in each case corresponds to a row of Table A.
Table 263
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2OCH3, and A
in each case corresponds to a row of Table A.
Table 264
Compounds of the formula lA wherein Q1 denotes methyl, Q3 denotes CH2OCH2CH3,
and A in each case corresponds to a row of Table A.
Table 265
Compounds of the formuia IA wherein Q1 denotes methyi, Q3 denotes CH2SCH3, and A
in each case corresponds to a row of Tabie A. '
Table 266
Compounds of the formula IA wherein Q1 denotes methyl, G3 denotes CH2SCH2CH3,
and A in each case corresponds to a row of Table A.
Table 267
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2S(=Q)CH3,
and A in each case corresponds to a row of Table A.
Table 268
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes
CH2S(=0)CH2CH3, and A in each case corresponds to a row of Table A.
Table 269
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2S0=O)2CH3,
and A in each case corresponds to a row of Tabie A.
Table 270
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes
CH2S(=0)2CH2CH3, and A in each case corresponds to a row of Table A.
Table 271
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes -OS(=0)2CH3,
and A in each case corresponds to a row of Table A.
Table 272
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes
-OS(=0)2CH2CH3, and A in each case corresponds to a row of Table A.

47
Table 273
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes
-OS(=0)2CH2CF3, and A in each case corresponds to a row of Table A.
Tgble 274
Compounds of the formula !A wherein Q1 denotes methyl, Q3 denotes -OS(-0)2CClF2,
and A in each case corresponds to a row of Table A.
Table 275
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OC(=0)CF3, and
A in each case corresponds to a row of Table A.
Table 276
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes NHCH2CF3, and
A in each case corresponds to a row of Table A.
Table 277
Compounds of the formula !A wherein Q1 denotes methyl, Q3 denotes
OCrVcyciopropyl, and A in each case corresponds to a row of Table A.
Table 278
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2C(CI)=CH2,
and A in each case corresponds to a row of Table A.
Table 279
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2CFNCF2,
and A in each case corresponds to a row of Table A.
Table 280
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes NHS(=0)2CF3,
and A in each case corresponds to a row of Table A.
Table 281
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes NHC(=0)CF3,
and A in each case corresponds to a row of Table A.
Table 282
Compounds of the formula SA wherein Q1 denotes methyl, Q3 denotes OCH2CN, and A
in each case corresponds to a row of Table A.
Table 283

48
Compounds of the formula [A wherein Q1 denotes methyl, Q3 denotes OCH2NO2, and
A in each case corresponds to a row of Table A.
Table 284
Compounds of the formula !A wherein Q1 denotes methyl, Q3 denotes cyclopropyloxy,
and A in each case corresponds to a row of Table A.
Table 285
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2OCHF2, and
A in each case corresponds to a row of Table A.
Table 286
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes Ch'2S(=0)2CHF2,
and A in each case corresponds to a row of Table A
Table 287
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH=NOCH3, and
A in each case corresponds to a row of Table A.
Table 288-
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH=NOCH2CH3,
and A in each case corresponds to a row of Table A.
Table 289
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes
CH=NOCH(CH3)2and A in each case corresponds to a row of Table A.
Table 290
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH=NOC(CH3)3,
and A in each case corresponds to a row of Table A.
Table 291
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes C(CH3)=NOCH3,
and A in each case corresponds to a row of Table A.
Table 292
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes
C(CH3)=NOCH2CH3, and A in each case corresponds to a row of Table A.
Table 293
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes
C(CH3)::::NOCH(CH3)2! and A in each case corresponds to a row of Table A.

49
Tabie294
Compounds of the formula !A wherein Q1 denotes rnethyf, Q3 denotes
C(CH3)=NOC{CH3)3, and A in each case corresponds to a row of Table A.
I sule A


50


51


52



53
Table 295
Compounds of the formula IA (as defined above) wherein Q1 denotes hydrogen, Q3
denotes CF3, and A in each case corresponds to a row of Table B.
Table 296
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes bromine, and
A in each case corresponds to a row of Table B.
Table 297
Compounds of the formula iA wherein Q1 denotes hydrogen, Q3 denotes chlorine, and
A in each case corresponds to a row of Table B,
Table 298
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH3, and A in
each case corresponds to a row of Table B.
Table 299
Compounds of the formula iA wherein Q1 denotes hydrogen, Q3 denotes OCH3, and A
in each case corresponds to a row of Table B.
Table 300

54
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCHCH2, and
A in each case corresponds to a row of Table B.
Table 301
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes ethoxy, and A
in each case corresponds to a row of Table B.
Table 302
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
OCH2CHFOCH3l and A in each case corresponds to a row of Table B.
Table 303
Comnounds of the formula IA wherein [" denotes h"dronen Q3 denotes
OCH2CH=CH2, and A in each case corresponds to a row of Tabie B,
Table 304
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH2CCH,
and A in each case corresponds to a row of Table B.
Table 305
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2OCH3,
and A in each case corresponds to a row of Table B.
Table 306
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
CH2OCH2CH3, and A in each case corresponds to a row of Table B.
Table 307
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2SCH3l
and A in each case corresponds to a row of Table B.
Table 308
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2SCH2CH3,
and A in each case corresponds to a row of Table B.
Table 309
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
CH2S(=0)CH3, and A in each case corresponds to a row of Table B.
Table 310
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
CH2S(=0)CH2CH3, and A in each case corresponds to a row of Table B.

.55
Table 311
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
CH2S(=0}2CH3, and A in each case corresponds to a row of Table B.
Table 312
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
CH2S(-0)2CH2CH3, and A in each case corresponds to a row of Table B.
Table 313
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes -OS(=0)2CH3j
and A in each case corresponds to a row of Table B.
Table 314
Compounds of the formula IA wherein Q1 denotes hydrogen, G3 denotes
-OS(=0)2CH2CH3, and A in each case corresponds to a row of Table B.
Table 315
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
-OS(=0)2CH2CF3, and A in each case corresponds to a row of Table B.
Table 316
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
-OS(=0)2CClF2! and A in each case corresponds to a row of Table B.
Table 317
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OC(=0)CF3,
and A in each case corresponds to a row of Table B.
Table 318
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes NHCH2CF3,
and A in each case corresponds io a row of Table B.
Table 319
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
OCH2-cyciopropyi, and A in each case corresponds \o a row of Table B.
Table 320
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
OCH2C(CI)=CH2> and A in each case corresponds to a row of Table B.
Table 321

56
Compounds of the formula [A wherein Q1 denotes hydrogen, Q3 denotes
OCH2CH=CF2, and A in each case corresponds to a row of Table B.
Table 322
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
NHS(=0)2CF3, and A in each case corresponds to a row of Table B,
Table 323
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes NHC(=0)CF3,
and A in each case corresponds to a row of Table B.
Table 324
fi-.rr!!-!!-.!!!-!.-!!! .".f tha fnrrv.::!-. !A u.-tmmis-i fM .-!,->.-,/v!v-.r. h.//JfftnDn .03 rloAfac. HfUIM onrl
in eacn Liaise: uuiiejjunus LU ci IUW ui L idurt! □.
Table 325
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH2NO2,
and A in each case corresponds to a row of Table B,
Table 326
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes cyciopropy-
loxy, and A in each case corresponds to a row of Table B.
Table 327
Compounds of the formula l A wherein Q1 denotes hydrogen, Q3 denotes CH2OCHF2,
and A in each case corresponds to a row of Table B.
Table 328
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
CH2S(=0)2CHF2, and A in each case corresponds to a row of Table B.
Table 329
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH=N0CH3,
and A in each case corresponds to a row of Table B.
Table 330
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
CH=NOCH2CH3, and A in each case corresponds to a row of Table B.
Table 331
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
CH=NOCH(CH3)2and A in each case corresponds to a row of Table B,

57
Table 332
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
CH=NOC(CH3)3, and A in each case corresponds to a row of Table B.
Tabie 333
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
C(Cri3)=NOCH3, and A in each case corresponds to a row of Tabie B,
Table 334
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
C Table 335.'
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
C(CH3)=NOCH(CH3)2, and A in each case corresponds to a row of Table B.
Table 336
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
C(CH3)=NOC(CH3)3, and A in each case corresponds to a row of Table B,
Table 337
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CF3, and A in
each case corresponds to a row of Table B.
Table 338
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes bromine, and A
in each case corresponds to a row of Table B.
Tabie 339
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes chlorine, and A
in each case corresponds to a row of Table B.
Table 340
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH3, and A in
each case corresponds to a row of Table B.
Table 341
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH3, and A in
each case corresponds to a row of Table B,
Table 342

58
Compounds of the'formula IA wherein Q1 denotes chlorine, Q3 denotes OCHCH2, and
A in each case corresponds to a row of Table B.
Table 343
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes ethoxy, and A
in each case corresponds to a row of Table B.
Tabie 344 '
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
OCH2CHFOCH3, and A in each case corresponds to a row of Table B.
Table 345
OUI IIL/UUI IUJ \Jl 11 IC IUII! lUld l/~V VVI ICI CIH VJ UCI IU1CO kjt IUJI II IC, W UCI ILJLCiO UW1 IVJl I -VJI 1,
and A in each case corresponds to a row of Tabie B,
Table 346
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2CCH, and
A in each case corresponds to a row of Tabie B.
Table 347
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2OCH3, and
A in each case corresponds to a row of Table B,
Table 348
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2OCH2CH3,
and A in each case corresponds to a row of Table B.
Table 349
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2SCH3, and
A in each case corresponds to a row of Table B.
Table 350
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2SCH2CH3,
and A in each case corresponds to a row of Table B.
Table 351
Compounds of the formula !A wherein Q1 denotes chlorine, Q3 denotes CH2S(=0)CH3,
and A in each case corresponds to a row of Table B.
Table 352
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
CH2S(=0)CH2CH3, and A in each case corresponds to a row of Table B.

59
Table 353
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2S(=0)2CH3,
and A in each case corresponds to a row of Table B.
Table 354
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
CH2S(=0)2CH2CH3, and A in each case corresponds to a row of Table B.
Table 355
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes -OS(-0)2CH3,
and A in each case corresponds to a row of Tab!e B.
Table 356
Compounds of the formula iA wherein Q1 denotes chlorine, Q3 denotes
-OS(=0)2CH2CH3, and A in each case corresponds to a row of Table B.
Table 357
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
-OS(=0)2CH2CF3, and A in each case corresponds to a row of Table B.
Table 358
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
-OS(=0)2CCIF2, and A in each case corresponds to a row of Table B.
Table 359
Compounds of the formula !A wherein Q1 denotes chlorine, Q3 denotes OC(=0)CF3,
and A in each case corresponds to a row of Table B.
Table 360
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes NHCH2CF3,
and A in each case corresponds to a row of Table B.
Table 361
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
OCH2-cyclopropyl, and A in each case corresponds to a row of Table B.
Table 362
Compounds of the formula !A wherein Q1 denotes chlorine, Q3 denotes
OCH2C(CI)=CH2, and A in each case corresponds to a row of Table B.
Table 363

60
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2CH=CF2,
and A in each case corresponds to a row of Table B.
Table 364
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes NHS(=0)2CF3,
and A in each case corresponds to a row of Table B.
Table 365
Compounds of the formula IA wherein Q1 denotes chiorine, Q3 denotes NHC(=0)CF3,
and A in each case corresponds to a row of Table B.
Table 366
Compounds of the formula iA wherein Q1 denotes chlorine, Q3 denotes OCH2CN, and
A in each case corresponds to a row of Table B.
Table 367
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2N02, and
A in each case corresponds to a row of Table B.
Table 368
Compounds of the formula [A wherein Q1 denotes chlorine, Q3 denotes cydopropyloxy,
and A in each case corresponds to a row of Table B.
Table 369
Compounds of the formula iA wherein Q1 denotes chlorine, Q3 denotes CH2OCHF2,
and A in each case corresponds to a row of Table B.
Table 370
Compounds of the formula IA wherein Q1 denotes chiorine, Q3 denotes
CH2S(=0}2CHF2, and A in each case corresponds to a row of Table B.
Table 371
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH=NOCH3,
and A in each case corresponds to a row of Table B.
Table 372
Compounds of the formula iA wherein Q1 denotes chlorine, Q3 denotes
CH=NOCH2CH3, and A in each case corresponds to a row of Table B.
Table 373
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
CH=NOCH(CH3)2and A in each case corresponds to a row of Table B.

61
Table 374
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
CH=NOC(CH3)3! and A in each case corresponds to a row of Tabie B.
Table 375
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
C(CH3)=NOCH3, and A in each case corresponds to a row of Tabie B.
Tabie 375
Compounds'of the formula IA wherein Q1 denotes chlorine, Q3 denotes
C(CH3)=NOCH2CH3, and A in each case corresponds to a row of Tabie B.
Table 377
Compounds of the formula !A wherein Q1 denotes chlorine, Q3 denotes
C{CH3)=NOCH(CH3)2, and A in each case corresponds to a row of Tabie B.
Tabie 378
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
C(CH3)=NOC(CH3)3, and A in each case corresponds to a row of Table B.
Table 379
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CF3, and A in
each case corresponds to a row of Table B.
Table 380
Compounds of the formula JA wherein Q1 denotes bromine, Q3 denotes bromine, and A
in each case corresponds to a row of Table B.
Table 381
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes chlorine, and A
in each case corresponds to a row of Tabie B.
Tabie 382
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH3, and A in
each case corresponds to a row of Table B.
Table 383
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH3, and A in
each case corresponds to a row of Table B.
Table 384

62
Compounds of the formula [A wherein Q1 denotes bromine, Q3 denotes OCHCH2, and
A in each case corresponds to a row of Table B.
Table 385 .
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes ethoxy, and A
in each case corresponds to a row of Table B.
Tabie386
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
OCH2CHFOCH3, and A in each case corresponds to a row of Table B.
Table 387
uunivuiiuo ui Lire luiiiiuia i/-\ wi ie;i tsin i' utsiiuies uiuiimit;, w ueMUieb uunjun-un;,
and A in each case corresponds to a row of Table B.
Table 388
Compounds of the formula !A wherein Q1 denotes bromine, Q3 denotes OCH2CCH,
and A in each case corresponds to a row of Table B.
Table 389
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2OCH3, and
A in each case corresponds to a row of Table B.
Table 390
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2OCH2CH3l
and A in each case corresponds to a row of Table B.
Table 391
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2SCH3, and
A in each case corresponds to a row of Table B.
Table 392
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2SCH2CH3,
and A in each case corresponds lo a row of Table B.
Table 393
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2S(=0)CH3,
and A in each case corresponds to a row of Table B.
Table 394
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
CH2S(=0)CH2CH3, and A in each case corresponds to a row of Table B.

63
Table 395
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2S(=0)2CH3,
and A in each case corresponds to a row of Table B.
Tabie 396
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
CH2S(=0)2CH2CH3, and A in each case corresponds to a row of Table B.
Table 397
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes -OS(=0}2CH3,
and A in each case corresponds to a row of Table B.
Tabie 398
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
-OS(=0)2CH2CH3, and A in each case corresponds to a row of Table B.
Table 399
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
-OSOChbCFa, and A in each case corresponds to a row of Table B.
Table 400
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
-0S{=0)2CCIF2, and A in each case corresponds to a row of Table B.
Table 401
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OC(=0)CF3,
and A in each case corresponds to a row of Table B.
Table 402
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes NHCH2CF3,
and A in each case corresponds to a row of Table B.
Table 403
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
OCH2-cycfopropyl, and A in each case corresponds to a row of Table B.
Table 404
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
OCH2C(CI)=CH2, and A in each case corresponds to a row of Table B.
Table 405

64
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2CH=CF2~, and A in each case corresponds to a row of Table B.
Table 406
Compounds of the formula !A wherein Q1 denotes bromine, Q3 denotes NHS{=0)2CF3!
and A in each case corresponds to a row of Table B.
Table 407
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes NHC(=0)CF3,
and A in each case corresponds to a row of Table B.
Table 408
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2CN, and
A in each case corresponds to a row of Table B.
Table 409
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2N02, and
A in each case corresponds to a row of Table B.
Table 410
Compounds of the formula !A wherein Q1 denotes bromine, Q3 denotes cyclopropyloxy,
and A in each case corresponds to a row of Table B.
Table 411
Compounds of the formula !A wherein Q1 denotes bromine, Q3 denotes CH2OCHF2,
and A in each case corresponds to a row of Table B.
Table 412
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
CH2S(=0)2CHF2, and A in each case corresponds to a row of Table B.
Table 413
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH=NOCH3,
and A in each case corresponds to a row of Table B.
Table 414
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
CH=NOCH2CH3, and A in each case corresponds to a row of Table B.
Table 415
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
CH=NOCH(CH3)2 and A in each case corresponds to a row of Table B.

65
Table 416
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
CH=NOC(CH3)3, and A in each case corresponds to a row of Table B.
Table 417
Compounds of the formula iA wherein Q1 denotes bromine, Q3 denotes
C(CH3)=NOCH3l and A in each case corresponds to a row of Table B.
Table 418
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
C(CH3)=NOCH2CH3t and A in each case corresponds to a row of Table B.
Table 419
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
C(CH3)=NOCH(CH3)2, and A in each case corresponds to a row of Table B.
Table 420
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
C(CH3)=NOC(CH3)3, and A in each case corresponds to a row of Tabie B.
Table 421
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CF3, and A in
each case corresponds to a row of Table B.
Table 422
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes bromine, and A
in each case corresponds to a row of Table B.
Table 423
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes chlorine, and A
in each case corresponds to a row of Table B.
Table 424
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH3, and A in
each case corresponds to a row of Table B.
Table 425 .
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH3, and A in
each ease corresponds to a row of Table B.
Table 426

66
Compounds of the formula iA wherein-Q1 denotes, fluorine, Q3 denotes OCHCH2! and A
in each case corresponds to a row of Table B.
Table 427
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes ethoxy, and A in
each case corresponds to a row of Table B.
Table 428
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
OCH2CHFOCH3, and A in each case corresponds to a row of Table B.
Table 429
UUI MjJUUI Ii_l3 (_J1 LI It3 IUI I HUIC3 \l~\ Wl id CI I ] W UCi iUtCO iiUUI II 1C, Vj and A in each case corresponds to a row of Table 8.
Table 430
Compounds of the formula iA wherein Q1 denotes fluorine, Q3 denotes OCH2CCH, and
A in each case corresponds to a row of Table B,
Table 431
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2OCH3, and
A in each case corresponds to a row of Table B.
Table 432
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2OCH2CH3,
and A in each case corresponds to a row of Table B.
Table 433
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2SCH3, and
A in each case corresponds to a row of Table B,
Table 434
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2SCH2CH3,
and A in each case corresponds to a row of Table B.
Table 435
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2S(=0)CH3,
and A in each case corresponds to a row of Table B.
Table 436
Compounds of the formula (A wherein Q1 denotes fluorine, Q3 denotes
CH2S(=0)CH2CH3, and A in each case corresponds to a row of Table B.

67
Table 437
Compounds of the formula IA wherein Q1 denotes fluorine, G3 denotes CH2S(=0)2CH3!
and A in eaqh case corresponds to a row of Table B,
Table 438
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
CH2S(=0)2CH2CH3, and A in each case corresponds to a row of Table B.
Table 439
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes -OS(=0)2CH3,
and A in each case corresponds to a row of Table B,
Table 440
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
-OS(=0)2CH2CH3, and A in each case corresponds to a row of Table B.
Table 441
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
-OS(=0)2CH2CF3, and A in each case corresponds to a row of Table B.
Table 442
Compounds of the formula [A wherein Q1 denotes fluorine, Q3 denotes-OS(=0)2CClF2,
and A in each case corresponds to a row of Table B.
Table 443
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OC(=0)CF3,
and A in each case corresponds to a row of Table B,
Table 444
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes NHCH2CF3, and
A in each case corresponds to a row of Table B.
Table 445
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
OCH2-cyclopropyl, and A in each case corresponds to a row of Table B.
Table 446
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
OCH2C(CI)=CH2, and A in each case corresponds to a row of Table B.
Table 447

68
Compounds of the formula 1A wherein Q1 denotes fluorine, Q3 denotes OCH2CH=CF2,
and A in each case corresponds to a row of Tabie B.
Table 448
Compounds of the formula lA wherein Q1 denotes fluorine, Q3 denotes NHS(=0)2CF3,
and A in each case corresponds to a row of Table B.
Table 449
Compounds of the formula IA wherein Q'1 denotes fluorine, Q3 denotes NHC(=0)CF3,
and A in each case corresponds to a row of Table B.
Table 450
Compounds of the formula SA wherein Q1 denotes fluorine, Q3 denotes OCH2CN, and A
in each case corresponds to a row of Table B.
Table 451
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH2NO2, and
A in each case corresponds to a row of Tabie B.
Table 452
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes cyclopropyloxy,
and A in each case corresponds to a row of Tabie B.
Table 453
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2OCHF2, and
A in each case corresponds to a row of Table B,
Table 454
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
CH2S(=0)2CHF2, and A in each case corresponds to a row of Table B.
Tabie 455
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH=NOCH3,
and A in each case corresponds to a row of Table B.
Table 456
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
'CH-NOCH2CH3, and A in each case corresponds to a row of Table B.
Table 457
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
CH=NOCH(CH3)2 and A in each case corresponds to a row of Table B.

69
Table 458
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
CH=NOC(CH3)3) and A in each case corresponds to a row of Table B.
Table 459
Compounds of the formula IA wherein Q1 denotes-fluorine, Q3 denotes
C(CH3)=NOCH3, and A in each case corresponds to a row of Table B.
Table 460
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
C(CH3)=NOCH;CH3s and A in each case corresponds to a row of Table B.
Table 461
Compounds of the formula !A wherein Q1 denotes fluorine, G3 denotes
C(CH3)=NOCH(CH3)2, and A in each case corresponds to a row of Table B.
Table 462
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
C(CH3)=NOC(CH3)3, and A in each case corresponds to a row of Tabie B.
Table 463
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CF3, and A in
each case corresponds to a row of Table B.
Table 464
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes bromine, and A in
each case corresponds to a row of Table B.
Table 465
Compounds of the formula (A wherein Q1 denotes iodine, Q3 denotes chlorine, and A in
each case corresponds to a row of Table B.
Table 466
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH3, and A in
each case corresponds to a row of Table B.
Table 467
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH3, and A in
each case corresponds to a row of Table B,
Table 468

70 :;
'Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCHCH2, and A
in each case corresponds to a row of-Table B.
Table 469
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes eihoxy, and A in
each case corresponds to a row of Table B.
Table 470
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2CHFOCH3,
and A in each case corresponds to a row of Table B.
Table 471
Compounds of the formuia iA wherein Q1 denotes iodine, Q3 denotes OCH2CH=Cf-i2,
and A in each case corresponds to a row of Table B,
Table 472
Compounds of the formuia IA wherein Q1 denotes iodine, Q3 denotes OCH2CCH, and
A in each case corresponds to a row of Tabie B.
Table 473
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2OCH3, and A
in each case corresponds to a row of Table B.
Table 474
Compounds of the formuia iA wherein Q1 denotes iodine, Q3 denotes CH2OCH2CH3,
and A in each case corresponds to a row of Table B.
Table 475
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2SCH3, and A
in each case corresponds to a row of Table B.
Table 476
Compounds of the formuia iA wherein Q1 denotes iodine, Q3 denotes CH2SCH2CH3,
and A in each case corresponds to a row of Table B.
Table 477
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2S(=0)CH3,
and A in each case corresponds to a row of Table B,
Table 478
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes
CH2S(=0}CH2CH3, and A in each case corresponds to a row of Table B.

71
Table 479
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2S(=0)2CH3,
and A in each case corresponds to a row of Table B.
Table 480
Compounds of the formuia iA wherein Q1 denotes iodine, Q3 denotes
CH2S(=0)2CH2CH3, and A in each case corresponds to a row of Table B.
Table 481
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes -OSOCHs,
and A in each case corresponds to a row of Table B.
Table 482
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes
-OS(=0)2CH2CH3, and A in each case corresponds to a row of Table B.
Table 483
Compounds of the formula iA wherein Q1 denotes iodine, Q3 denotes
-OS(=0)2CH2CF3, and A in each case corresponds to a row of Table B,
Table 484
Compounds of the formuia IA wherein Q1 denotes iodine, Q3 denotes -OS(=0)2CCIF2,
and A in each case corresponds to a row of Table B.
Table 485
Compounds of the formula !A wherein Q1 denotes iodine, Q3 denotes OC(=0)CF3, and
A in each case corresponds to a row of Table B.
Table 486
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes NHCH2CF3, and
A in each case corresponds to a row of Table B.
Table 487
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes
OCFfe-cyclopropyl, and A in each case corresponds to a row of Table B.
Table 488
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2C(Ci)=CH2,
and A in each case corresponds to a row of Table B,
Table 489

72
Compounds of the formula [A wherein Q1 denotes iodine, Q3 denotes OCH2CH=CF2,
and A in each case corresponds to a row of Table B.
Table 490
Compounds of the formula SA wherein Q1 denotes iodine, Q3 denotes NHS(=0)2CF3!
and A in each case corresponds to a row of Table B.
Table 491
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes NHC(=0)CF3l
and A in each case corresponds to a row of Table B.
Table 492
Compounds of the formula IA wherein Cr denotes iodine, QJ denotes OGH2CPV, and A
in each case corresponds to a row of Table B.
Table 493
Compounds of the formula IA wherein Q1 denotes iodine, G3 denotes OCH2NO2, and A
in each case corresponds to a row of Table B.
Table 494
Compounds of the formula !A wherein Q1 denotes iodine, Q3 denotes cyclopropyloxy,
and A in each case corresponds to a row of Table B.
Table 495
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2OCHF2, and
A in each case corresponds to a row of Table B.
Table 496
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2S(=0)2CHF2,
and A in each case corresponds to a row of Table B.
Table 497
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH=NOCH3, and
A in each case corresponds to a row of Table B.
Table 498
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH=NOCH2CH3,
and A in each case corresponds to a row of Table B,
Table 499
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH=NOCH(CH3)2
and A in each case corresponds to a row of Table B.

• 73
Table 500
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH=NOC{CH3)3,
and A in each case corresponds to a row of Table B.
Table 501
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes C(CH3)=NOCH3,
and A in each case corresponds to a row of Table B.
Table 502
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes
C(CH3)=NOCH2CH3, and A in each case corresponds to a row of Table B.
Table 503
Compounds of the formula !A wherein Q1 denotes iodine, Q3 denotes
C(CH3)=NOCH(CH3)2, and A in each case corresponds to a row of Table B.
Table 504
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes
C(CH3)=NOC(CH3)3, and A in each case corresponds to a row of Table B.
Table 505
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CF3, and A in
each case corresponds to a row of Table B.
Table 506
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes bromine, and A in
each case corresponds to a row of Table B.
Table 507
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes chlorine, and A in
each case corresponds to a row of Table B.
Table 508
Compounds of the formula !A wherein Q1 denotes cyano, Q3 denotes CH3, and A in
each case corresponds to a row of Table B.
Table 509
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH3, and A in
each case corresponds to a row of Table B.
Table 510

74
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCHCH2, and A
in each case corresponds to a row of Table B.
Table 511
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes ethoxy, and A in
each case corresponds to a row of Table B,
Table 512
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2CHFOCH3,
and A in each case corresponds to a row of Table B.
Table 513
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OChSCrCHa,
and A in each case corresponds to a row of Table B.
Table 514
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2CCH, and
A in each case corresponds to a row of Table B.
Table 515
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2OCH3, and A
in each case corresponds to a row of Table B.
Table 516
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2OCH2CH3,
and A in each case corresponds to a row of Table B.
Table 517
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2SCH3, and A
in each case corresponds to a row of Table B. .
Table 518
Compounds of the formula iA wherein Q1 denotes cyano, Q3 denotes CISCi-feCHs,
and A in each case corresponds to a row of Table B.
Table 519
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2S(=0)CH3,
and A in each case corresponds to a row of Table B.
Table 520
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes
CH2S(=0)CH2CH3, and A in each case corresponds to a row of Table B.

.75
Table 521
Compounds of the formula !A wherein Q1 denotes cyano, G3 denotes CH2S{=0)2CH3,
and A in each case corresponds to a row of Table B.
Table 522
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes
CH2S(=0)2CH2CH3, and A in each case corresponds to a row of Table B.
Table 523
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes -OS(=0)2CH3,
and A in each case corresponds to a row of TabSe B.
Table 524
Compounds of the formula [A wherein Q1 denotes cyano, Q3 denotes
-OS(=0)2CH2CH3, and A in each case corresponds to a row of Table B.
Table 525
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes
-OS(=0)2Ch'2CF3, and A in each case corresponds to a row of Table B.
Table 526
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes -OS{=0)2CClF2>
and A in each case corresponds to a row of Table B.
Table 527
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OC(=0)CF3, and
A in each case corresponds to a row of Table B.
Table 528
Compounds of the formula iA wherein Q1 denotes cyano, Q3 denotes NHCH2CF3, and
A in each case corresponds to a row of Table B.
Table 529
Compounds of the formula IA wherein Q5 denotes cyano, Q3 denotes
OChVcyclopropyl, and A in each case corresponds to a row of Tabie B.
Table 530
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2C(CI)=CH2,
and A in each case corresponds to a row of Table B.
Table 531

76
Compounds of the formula 1A wherein Q1 denotes cyano, Q3 denotes OCH2CH=CF2,
and A in each case corresponds to a row of Table B. .. .
Table 53-2
Compounds of the formula IA Wherein Q1 denotes cyano, Q3 denotes NHS(=0)2CF3,
and A in each case corresponds to a row of Table B.
Table 533
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes NHC(=0)CF3,
and A in each case corresponds to a row of Table B.
Table 534
Compounds of the formula iA wherein Q' denotes cyano, Q3 denotes OCH2CN, and A
in each case corresponds to a row of Table B.
Table 535
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2NO2, and A
in each case corresponds to a row of Table B.
Table 536
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes cyciopropyloxy,
and A in each case corresponds to a row of Table B.
Tabie 537
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2OCHF2, and
A in each case corresponds to a row of Table B.
Table 538
Compounds of the formula !A wherein Q1 denotes cyano, Q3 denotes CH2S(=0)2CHF2,
and A in each case corresponds to a row of Table B.
Table 539
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH=NOCH3, and
A in each case corresponds to a row of Table B.
Table 540
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH=NOCH2CH3,
and A in each case corresponds to a row of Tabie B.
Table 541
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH=NOCH(CH3)2
and A in each case corresponds to a row of Tabie B.

77
Table 542
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH=NOC(CH3)3,
and A in each case corresponds to a row of Table 8.
Table 543
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes C(CH3}=NOCH3,
and A in each case corresponds to a row of Table B.
Table 544
Compounds of the formula i A wherein Q1 denotes cyano, Q3 denotes
C(CH3)=NOCH2Crl3) and A in each case corresponds to a row of Table B.
Table 545
Compounds of the formula IA wherein Q1 denotes cyanoyQ3 denotes
C(CH3)=NOCH(CH3)2, and A in each case corresponds to a row of Table B.
Table 546
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes
C(CH3)=NOC{CH3)3, and A in each case corresponds to a row of Table B.
Table 547
Compounds of theformula IA wherein Q1 denotes methyl, Q3 denotes CF3, and A in
each case corresponds to a row of Table B.
Table 548
Compounds of theformula IA wherein Q1 denotes methyl, Q3 denotes bromine, and A
in each case corresponds to a row of Table B.
Table 549
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes chlorine, and A
in each case corresponds to a row of Table B.
Table 550
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH3, and A in
each case corresponds to a row of Table B.
Table 551
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH3, and A in
each case corresponds to a row of Table B.
Table 552

78
Compounds of the formula (A wherein Q1 denotes methyl, Q3 denotes OCHCH2, and A
' in each case corresponds to a row of Table B.
Table 553
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes ethoxy, and A in
each case corresponds to a row of Table B.
Table 554
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2CHFOCH3,
and A in each case corresponds to a row of Table B.
Table 555
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OC-H2CH=CH2j
and A in each case corresponds to a row of Table B.
Table 556
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCHbCCH, and
A in each case corresponds to a row of Table B.
Table 557
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2OCH3, and A
in each case corresponds to a row of Table B.
Table 558
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2OCH2CH3,
and A in each case corresponds to a row of Table B.
Table 559
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2SCH3, and A
in each case corresponds to a row of Table B.
Table 560
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CHSCI-kCHs,
and A in each case corresponds to a row of Table B.
Table 561
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2S(=0)CH3,
and A in each case corresponds to a row of Table B.
Table 562
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes
CH2S(=0)CH2CH3, and A in each case corresponds to a row of Table B.

• 79 ..." *-.-:;
Tabie563
Compounds of the formula 1A wherein Q1 denotes methyl, Q3 denotes CH2S(=0)2CH3,
and A in each case corresponds to a row of Table B,
Table 564
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes
CH2S(=0)2CH2CH3, and A in each case corresponds to a row of Table B.
Table 565
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes -OS(=0)2CH3,
and A in each case corresponds to a row of Tabie B.
Table 566
Compounds of the formula !A wherein Q1 denotes methyl,'Q3 denotes
-OS(=0)2CH2CH3, and A in each case corresponds to a row of Table B.
Table 567
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes
-OS(=0)2CH2CF3, and A in each case corresponds to a row of Table B.
Table 568
Compounds of the formula !A wherein Q1 denotes methyl, Q3 denotes -OS(=0)2CCIF2,
and A in each case corresponds to a row of Table B.
Table 569
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OC(=0)CF3, and
A in each case corresponds to a row of Tabie B.
Tabie 570
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes NHCH2CF3, and
A in each case corresponds to a row of Table B.
Table 571
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes
OChVcyclopropyl, and A in each case corresponds to a row of Table B.
Table 572
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2C(CI)=CH2)
and A in each case corresponds to a row of Table B.
Table 573

80
Compounds .of the formula IA wherein G1 denotes methyl, Q3 denotes OCH2CH=CF2,
and A in each case corresponds to a row of Table B.
Table 574
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes NHS(=0)2CF3,
and A in each case corresponds to a row of Table 8.
Table 575
Compounds of the formula IA wherein Q1 denotes methy!, Q3 denotes NHC(=0)CF3,
and A in each case corresponds to a row of Table B.
Table 576
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2CN, and A
in each case corresponds to a row of Table B.
Table 577
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2NO2, and
A in each case corresponds to a row of Table B.
Table 578
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes cyclopropyloxy,
and A in each case corresponds to a row of Table B.
Table 579
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH20CHF2) and
A in each case corresponds to a row of Table B.
Table 580
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2S(=0)2CHF2,
and A in each case corresponds to a row of Table B.
Table 581
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH=NOCH3l and
A in each case corresponds to a row of Table B.
Table 582
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH=NOCH2CH3,
and A in each case corresponds to a row of Table B.
Table 583
Compounds of the formula iA wherein Q1 denotes methyl, Q3 denotes
CH=NOCH(CH3)2and A in each case corresponds to a row of Table B.

81
Table 584'
Compounds of the formula !A wherein Q1 denotes methyl, Q3 denotes CH=NOC(CH3)3
-.and A in each case corresponds to a row of Table B.
Table 585
/ -_' i I i -yj \ ii I ; L: u vJi ti !V i \JI I i i U !Q IJ \ vVnti:! --C LJI fJivJ i I lull ijru V,t iwli1-. w w . jy 4 --V v , . _,
and A in each case corresponds to a row of Table B,
Table 586
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes
C(CH3)=NOCH2CH3, and A in each case corresponds to a row of Table B.
Table 587
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes
C(CH3)=NOCH(CH3)2, and A in each case corresponds to a row of Table B.
Table 588.
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes
C(CH3)=NOC{CH3)3, and A in each case corresponds to a row of Table B.
Table B

i . i ' i i
* denotes the binding site.-
Table 589
Compounds of the formula IA (as defined above) wherein Q* denotes hydrogen, Q3
denotes CF3, and A in each case corresponds to a row of Table C.

82
Table 590
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes bromine, and
A in each case corresponds to a row of Table C.
Table 591
Compounds of the formula (A wherein Q1 denotes hydrogen, Q3 denotes chlorine, and
A in each case corresponds to a row of Table C.
Table 592
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH3s and A in
eacn case corresponds xo a row OJ i aoie w.
Table 593
Compounds of the formula iA wherein Q1 denotes hydrogen, Q3 denotes OCH3, and A
in each case corresponds to a row of Table C.
Table 594
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCHCH2, and
A in each case corresponds to a row of Table C.
Table 595
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes ethoxy, and A
in each case corresponds to a row of Table C.
Table 596
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
OCH2CHFOCH3, and A in each case corresponds to a row of Table C.
Table 597
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
OCH2CH=CH2, and A in each case corresponds to a row of Table C.
Table 598
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH2CCH,
and A in each case corresponds to a row of Table C.
Table 599
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2OCH3,
and A in each case corresponds to a row-of Table C.
Table 600

83
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
CH2OCH2CH3, and A in each case corresponds to a row of Table C.
Table.601
Compounds of the formula (A wherein Q1 denotes hydrogen, Q3 denotes CH2SCH3,
and A in each case corresponds to a row of Table C.
Table 602 '
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2SCH?CH3,
and A in each case corresponds to a row of Table C.
Tabie603 .
Compounds of the formula iA wherein Q1 denotes hydrogen, Q3 denotes
GH2S(=0}CH3, and A in each case corresponds to a row of Table C.
Table 604
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
CH2S{=0)CH2CH3l and A in each case corresponds to a row of Table C.
Table 605
Compounds of the formula [A wherein Q1 denotes hydrogen, Q3 denotes
CH2S(=0)2CH3, and A in each case corresponds to a row of Table C.
Table 606
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
CH2S(=0)2CH2CH3, and A in each case corresponds to a row of Table C.
Table 607
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes -OS(=0)2CH3,
and A in each case corresponds to a row of Table C.
Table 608
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
-OS(=0)2CH2CH3, and A in each case corresponds to a row of Table C.
Table 609
Compounds of the formula !A wherein Q1 denotes hydrogen, Q3 denotes
-GS(=0)2CH2CF3, and A in each case corresponds to a row of Table C.
Table 610
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
-OS(-0)2CCIF2, and A in each case corresponds to a row of Table C.

84
Table 611
Compounds of the formula lA wherein Q1 denotes hydrogen, Q3 denotes OC(=0)CF3,
and A in each case corresponds to a row of Tabie C.
Table 612'
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes NHCH2CF3,
and A in each case corresponds to a row of Table C.
Table 613
Compounds of the formula iA wherein Q1 denotes hydrogen, Q3 denotes
OCrb-cyciopropyl, and A in each case corresponds to a row of Tabie C,
Tabie 614
Compounds of the formuia !A wherein Q1 denotes hydrogen, Q3 denotes
OCH2C(Ci)=CH2, and A in each case corresponds to a row of Table C.
Table 615
Compounds of the formula iA wherein Q1 denotes hydrogen, Q3 denotes
OCH2CH=CF2, and A in each case corresponds to a row of Table C.
Table 616
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
NHS(=0)2CF3, and A in each case corresponds to a row of Table C.
Table 617
Compounds of the formula iA wherein Q1 denotes hydrogen, Q3 denotes NHC(=0)CF3,
and A in each case corresponds to a row of Table C.
Table 618
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH2CN, and
A in each case corresponds to a row of Table C.
Table 619
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH2NO2,
and A in each case corresponds to a row of Table C.
Table 620
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes cyclopropy-
loxy, and A in each case corresponds to a row of Tabie C.
Table 621

85
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH20CHF2l
and A in each case corresponds to a row of Tabie C. Table 622 . • .
• Compounds of the formula (A wherein Q1 denotes hydrogen, Q3 denotes
CH2S(=0)2CHF2, and A in each case corresponds to a row of Table C.
Table 623 .,-'
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH=NOCH3,
and A in each case corresponds to a row of Table C.
Table 624
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
CH=NOCH2CH3] and A in each case corresponds to a row of Table C,
Table 625
Compounds of the formula ! A wherein Q1 denotes hydrogen, Q3 denotes
CH=NOCH(CH3)2and A in each case corresponds to a row of Table C.
Table" 626
Compounds of the formula !A wherein Q1 denotes hydrogen, Q3 denotes
CH=NOC(CH3)3, and A in each case corresponds to a row of Table C.
Table 627
Compounds of the formula IA wherein Q1 denotes hydrogen, G3 denotes
C(CH3)=NOCH3, and A in each case corresponds to a row of Table C.
Table 628
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
C(CH3)=NOCH2CH3, and A in each case corresponds to a row of Table C.
Table 629
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
C(CH3)~NOCH(CH3)2, and A in each case corresponds to a row of Table C.
Table 630
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
C(CH3)=NOC(CH3)3, and A in each case corresponds to a row of Tabie C.
Table 631
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CF3, and A in
each case corresponds to a row of Table C.

86
Table 632
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes bromine, and A
in each case corresponds to a row of Tabie C.
Table 633
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes chlorine, and A
in each case corresponds to a row of Table C,
Tabie 634
Compounds of the formula SA wherein Q1 denotes chlorine, Q3 denotes CHs, and A in
each case corresponds to a row of Table C.
T_UI. r* ! clUStt OOD
Compounds of the formula IA wherein Q1 denotes chiorine, Q3 denotes OCH3, and A in
each case corresponds to a row of Tabie C.
Table 636
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCHCH2, and
A in each case corresponds to a row of Table C.
Table 637
Compounds of the formula !A wherein Q1 denotes chlorine, Q3 denotes ethoxy, and A
in each case corresponds to a row of Tabie C.
Table 638
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
OCH2CHFOCH3, and A in each case corresponds to a row of Table C.
Tabie 639
Compounds of the formula !A wherein Q1 denotes chlorine, Q3 denotes OCfGHChb,
and A in each case corresponds to a row of Table C.
Table 640
Compounds of the formula IA wherein Q1 denotes chiorine, Q3 denotes OCH2CCH, and
A in each case corresponds to a row of Table C.
Table 641
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2OCH3, and
A in each case corresponds to a row of Table C.
Table 642

87
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2OCH2CH3,
and A in each case corresponds to a row of Table C.
Table 643
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2seH3l and
A in each case corresponds to a row of Table C.
Table 644 .". ". "
Compounds of the formula !A whereirvG1 denotes chlorine, Q3 denotes CH-2SCH2CH3,
and A in each case corresnonds to a row of Table C,
Table 645
Compounds of the formula !A wherein Q1 denotes chlorine, Q3 denotes CH2S(=0)CH3,
and A in each case corresponds to a row of Table C.
Table 646
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
CH2S(=0)CH2CH3, and A in each case corresponds to a row of Table C,
Table 647
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2S(=0)2CH3,
and A in each case corresponds to a row of Table C.
Table 648
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
CH2S(=0)2CH2CH3, and A in each case corresponds to a row of Table C.
Table 649
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes -OS{=0)2CH3,
and A in each case corresponds to a row of Table C.
Table 650
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
-0S(=O)2CH2CH3, and A in each case corresponds to a row of Table C.
Table 651
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
-OS(=0)2CH2CF3, and A in each case corresponds to a row of Table C.
Table 652
Compounds of the formula SA wherein Q1 denotes chlorine, Q3 denotes
-OS(=0)2CCIF2, and A in each case corresponds to a row of Table C.

88
Table 653
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OC(=0)CF3,
and A in each case corresponds to a row of Table C.
' Table 654
Compounds of the formula !A wherein Q1 denotes chlorine, Q3 denotes NHCH2CF3!
and A in each case corresponds to a row of Table C.
Table 655
Compounds of the formula !A wherein Q1 denotes chlorine, Q3 denotes
OCH2-cyc!opropyi) and A in each case corresponds to a row of Table C.
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
OCH2C(CI)=CH2, and A in each case corresponds to a row of Table C.
Table 657
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2CH=CF2l
and A in each case corresponds to a row of Table C.
Table 658
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes NHS(=0)2CF3,
and A in each case corresponds to a row of Table C.
Table 659
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes NHC(=0)CF3j
and A in each case corresponds to a row of Table C.
Table 660
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2CN, and
A in each case corresponds to a row of Table C.
Table 661
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2N02, and
A in each case corresponds to a row of Table C.
Table 662
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes cyclopropyloxy,
and A in each case corresponds to a row of Table C.
Table 663

89
Compounds of the formula 1A wherein Q1 denotes chlorine, Q3 denotes CH20CHF2,
and A in each case corresponds to a row of Table C.
Table 664
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
CH2S(=0)2CHF2, and A in each case corresponds to a row of Table C.
Table 665
Compounds of the formula LA wherein Q1 denotes chlorine, Q3 denotes CH-MOCH3,
and A in each case corresponds to a row of Table C.
Table 666
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
CH=NOCH2CH3! and A in each case corresponds to a row of Table C.
Table'667
Compounds of the formula !A wherein Q1 denotes chlorine, Q3 denotes
CH=NOCH(CH3)2and A in each case corresponds to a row of Tabie C.
Table 668
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
CH=NOC(CH3)3, and A in each case corresponds to a row of Table C,
Tabie 669
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
C(CH3)=NOCH3, and A in each case corresponds to a row of Table C.
Table 670
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
C(CH3)=NOCH2CH3> and A in each case corresponds to a row of Table C.
Table 671
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
C(CH3}=NOCH(CH3)2, and A in each case corresponds to a row of Table C.
Table 672
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
C(CH3)=NOC(CH3)3, and A in each case corresponds to a row of Table C.
Table 673
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CF3, and A in
each case corresponds to a row of Table C.

90
Table 674" -
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes bromine, and A
in each case corresponds to a row of Table C.
Table 675
Compounds of the formula LA wherein Q1 denotes bromine, Q3 denotes chlorine, and A
in each case corresponds to a row of Table C.
Table 676
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes C'rb, and A in
each case corresponds to a row of Table C.
i ao\e ot {
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH3, and A in
each case corresponds to a row of Table C.
Table 678
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCHCH2, and
A in each case corresponds to a row of Table C.
Table 679
Compounds of the formula f A wherein Q1 denotes bromine, Q3 denotes ethoxy, and A
in each case corresponds to a row of Table C.
Table 680
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
OCH2CHFOCH3, and A in each case corresponds to a row of Table C,
Table 681
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2CH=CH2,
and A in each case corresponds to a row of Table C.
Table 682
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2CCH,
and A in each case corresponds to a row of Table C.
Table 683
Compounds of-the formula IA wherein Q1 denotes bromine, Q3 denotes CH2OCH3, and
A in each case corresponds to a row of Table C.
Table 684

91
Compounds of the formula IA wherein'Q1 denotes bromine, Q3 denotes CH20CH2CH3,
and A in each case corresponds to a row of Table C.
Table 685
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2SCH3, and
A in each case corresponds to a row of Table C.
Table 686
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2SCH2CH3,
and A in each case corresponds to a row of Table C.
Table 687
Compounds of the formula SA wherein Q1 denotes bromine. Q3 denotes CH2S(=0)Ch'3s
and A in each case corresponds to a row of Table C.
Table 688
Compounds of the formula !A wherein Q1 denotes bromine, Q3 denotes
CHi>S(=0)CH2CH3, and A in each case corresponds to a row of Table C.
Table 689
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2S(=0)2CH3,
and A in each case corresponds to a row of Table C.
Table 690
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
CH2S(=0)2CH2CH3, and A in each case corresponds to a row of Table C.
Table 691
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes -OS(=0)2CH3,
and A in each case corresponds to a row of Table C.
Table 692
Compounds of the formula SA wherein Q1 denotes bromine, Q3 denotes
-OS(=0)2CH2CH3, and A in each case corresponds to a row of Table C.
Table 693
Compounds of the formula !A wherein Q1 denotes bromine, Q3 denotes
-OS{=0)2CH2CF3, and A in each case corresponds to a row of Table C.
Table 694
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
-OS(=0)2CCIF2, and A in each case corresponds to a row of Table C.

92
Table 695
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OC(=0)CF3,
and A in each case corresponds to a row of Table C.
Table 696
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes NHCHCFs,
and A in each case corresponds to a row of Table C.
Table 697
- Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
OChVcyclopropyl, and A in each case corresponds to a row of Table C.
Table 698
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
OCH2C(CI)=CH2, and A in each case corresponds to a row of Table C.
Table 699
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2CH=CF2,
and A in each case corresponds to a row of Table C.
Table 700
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes NHS(=0)2CF3,
and A in each case corresponds to a row of Table C.
Table 701
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes NHC(=0)CF3,
and A in each case corresponds to a row of Table C.
Table 702
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2CN, and
A in each case corresponds to a row of Table C.
Table 703
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2NO2, and
A in each case corresponds to a row of Table C.
Table 704
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes cyclopropyloxy,
and A in each case corresponds to a row of Table C.
Table 705

93
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2OCHF2,
and A in each case corresponds to a row of Table C.
Table 706
Compounds of the formula IA wherein Q1 denotes bromine, G3 denotes
CH2S(=0)2CHF2, and A in each case corresponds to a row of Table C.
Table 707
Compounds of the formula !A wherein Q) denotes bromine, Q3 denotes CH~NOCH3,
and A in each case corresponds to a row of Table C
Table 708
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
CH=iNOCH2CH3, and A In each case corresponds to a row of Table C.
Table 709
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
CH=NOCH(CH3)2and A in each case corresponds to a row of Table C.
Table 710
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
CH=NOC(CH3)3l and A in each case corresponds to a row of Table C.
Table 711
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
C(CH3)=NOCH3, and A in each case corresponds to a row of Table C.
Table 712
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
C(CH3)=NOCH2CH3, and A in each case corresponds to a row of Table C.
Table 713
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
C(CH3)=NOCH(CH3)2, and A in each case corresponds to a row of Table C.
Table 714
Compounds of the formula IA wherein G1 denotes bromine, Q3 denotes
C(CH3)=NOC(CH3)3, and A in each case corresponds to a row of Table C.
Table 715
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CF3, and A in
each case corresponds to a row of Table C.

94
Table 716
Compounds of the formula lAwherein Q1 denotes fluorine, Q3 denotes bromine, and A
in each case corresponds to a row of Table C.
Table 717
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes chlorine, and A
- in each case corresponds to a row of Table C.
Table 718
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH3, and A in
each case corresponds to a row of Table C.
Table 719
Compounds of the formula iA wherein Q1 denotes fluorine, Q3 denotes OCH3, and A in
each case corresponds to a row of Table C.
Table 720
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCHCH2, and A
in each case corresponds to a row of Table C,
Table 721
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes ethoxy, and A in
each case corresponds to a row of Table C.
Table 722
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
OCH2CHFOCH3, and A in each case corresponds to a row of Table C.
Table 723
Compounds of the formula (A wherein Q1 denotes fluorine, Q3 denotes OCH2CH=CH2,
and A in each case corresponds to a row of Table C.
Table 724
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH2CCH, and
A in each case corresponds to a row of Table C.
Table 725
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2OCH3, and
A in each case corresponds to a row of Table C.
Table 726

95
'Compounds of the formula 1A wherein Q1 denotes fluorine, Q3 denotes CH2OCH2CH3,
and A in each case corresponds to a row of Table C.
- Table 727
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2SCH3, and
A in each case corresponds to a row of Table C.
Table 728
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2SCH2CH3,
and A in each case corresponds to a row of Table C.
Table 729
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2S(=0)CH3,
and A in each case corresponds "to a row of Table C.
Table 730
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
CH2S(=0)CH2CH3, and A in each case corresponds to a row of Table C,
Table 731
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2S(=0)2CH3,
and A in each case corresponds to a row of Table C.
Table 732
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
CH2S{=0)2CH2CH3, and A in each case corresponds to a row of Table C.
Table 733
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes -OS(=0)2CH3,
and A in each case corresponds to a row of Table C.
Table 734
Compounds of theformuia IA wherein Q1 denotes fluorine, Q3 denotes
-0S(=O)2CH2CH3, and A in each case corresponds to a row of Table C.
Table 735
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
-OS(=0)2CH2CF3, and A in each case corresponds to a row of Table C.
Table 736
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes -OS(=0)2CClF2,
and A in each case corresponds to a row of Table C.

96
Table 737
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OC(=0)CF3,
and A in each case corresponds to a row of Table C.
Table 738
Compounds of ths formula IA wherein Q1 denotes fluorine, Q3 denotes NHCH2CF3, and
A in each case corresponds to a row of Table C.
Table 739
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
OCH2-cyclopropyi, and A in each case corresponds to a row of Table C.
Table 740
Compounds of the formula !A wherein Q1 denotes fluorine, Q3 denotes
OCH2C(Cl)=CH2, and A in each case corresponds to a row of Table C.
Table 741
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH2CH=CF2,
and A in each case corresponds to a row of Table C.
Table 742
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes NHS(=0)2CF3,
and A in each case corresponds to a row of Table C.
Table 743
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes NHC(=0)CF3,
and A in each case corresponds to a row of Table C.
Table 744
Compounds of the formula iA wherein Q1 denotes fluorine, Q3 denotes OCH2CN, and A
in each case corresponds to a row of Table C.
Table 745
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH2NO2, and
A in each case corresponds to a row of Table C.
Table 746
Compounds of the formula IA wherein Q1 denotesfluorine, Q3 denotes cydopropyloxy,
and A in each case corresponds to a row of Table C.
Table 747

97
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2OCHF2, and
A in each case corresponds to a row of Table.C.
Table 748
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
CH2S(=0)2CHF2, and A in each case corresponds to a row of Table C.
Table 749
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH=NOCH3,
and A in each case corresponds to a row of Table C.
Table 750
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
CHNOChbCHs, and A in each case corresponds to a row of Table C.
Table 751
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
CH=NOCH(CH3)2and A in each case corresponds to a row of Table C.
Table 752
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
CH=NOC(CH3)3, and A in each case corresponds to a row of Table C,
Table 753
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
C(CH3)=NOCH3, and A in each case corresponds to a row of Table C.
Table 754
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
C(CH3)=NOCH2CH3, and A in each case corresponds to a row of Table C.
Table 755
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
C(CH3)=NOCH(CH3)2, and A in each case corresponds to a row of Table C.
Table 756
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
C(CH3)=NOC(CH3)3, and A in each case corresponds to a row of Table C.
Table 757
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CF3, and A in
each case corresponds to a row of Table C.

98
Tabte 758
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes bromine, and A in
each case corresponds to a row of Table C.
Table 759
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes chlorine, and A in
each case corresponds to a row of Tabie C.
Table 760
Compounds of the formula iA wherein Q1 denotes iodine, Q3 denotes CH3, and A in
each case corresponds to a row of Table C.
Tabie 761
Compounds of the formula IA wherein Q1 denotes-iodine,Q3 denotes OCH3, and A in
each case corresponds to a row of Table C.
Table 762
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCHCH2, and A
in each case corresponds to a row of Table C.
Table 763
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes ethoxy, and A in
each case corresponds to a row of Table C.
Table 764
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2CHFOCH3,
and A in each case corresponds to a row of Table C,
Tabie 765
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCFCHChb,
and A in each case corresponds to a row of Table C.
Table 766
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2CCH, and
A in each case corresponds to a row of Table C.
Table 767
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2OCH3, and A
in each case corresponds to a row of Table C.
Table 768

99
Compounds of the formula 1A wherein Q1 denotes'iodine, Q3 denotes CH2OCH2CH3,
and A in each case corresponds to a row of Table C.
Table 769
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2SCH3, and A
in each case corresponds to a row of Table C.
Table 770
Compounds of theformuia IA wherein Q1 denotes iodine, Q3 denotes CH2SCH2CH3,
and A in each case corresponds to a row of Table'©.
Table 771 * .
Compounds of the formula LA wherein Q1 denotes iodine, Q3 denotes CH2S(-0)CHj,
and A in each case corresponds to a row of Table C.
Table 772
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes
CH2S(=0)CH2CH3, and A in each case corresponds to a row of Table C.
Table 773
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2S{=0)2CH3,
and A in each case corresponds to a row of Table C.
Table 774
Compounds of theformuia IA wherein Q1 denotes iodine, Q3 denotes
CH2S(=0)2CH2CH3, and A in each case corresponds to a row of Table C.
Table 775
Compounds of theformuia IA wherein Q1 denotes iodine, Q3 denotes -OSOCFb,
and A in each case corresponds to a row of Table C.
Table 776
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes
-OS(=0)2CH2CH3, and A in each case corresponds to a row of Table C.
Table 777
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes
-OS(=0)2CH2CF3, and A in each case corresponds to a row of Table C.
Table 778
Compounds of theformuia IA wherein Q1 denotes iodine, Q3 denotes -OS(=0)2CCIF2,
and A in each case corresponds to a row of Table C.

100
Table 779
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OC(=0)CF3,and
A in each case corresponds to a row of Table C.
Table 780
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes NHCH2CF3, and
A in each case corresponds to a row of Table C.
Table 781
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes
OCH2-cyclopropyl, and A in each case corresponds to a row of Table C.
Table 782
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OGH2C(CI)=CH2,
and A in each case corresponds to a row of Table C.
Table 783
Compounds of the formula IA wherein Q1 denotes iodine,. Q3 denotes OCH2CH=CF2,
and A in each case corresponds to a row of Table C.
Table 784
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes NHS(=0)2CF3,
and A in each case corresponds to a row of Table C.
Table 785
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes NHC(=0)CF3,
and A in each case corresponds to a row of Table C.
Table 786
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OChkCN, and A
in each case corresponds to a row of Table C,
Table 787
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2N02l and A
in each case corresponds to a row of Table C.
Table 788
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes cyclopropyloxy,
and A in each case corresponds to a row of Table C.
Table 789

101
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2OCHF2, and
A in each case corresponds to a row of Table C.
Table 790
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2S(=0)2CHF2,
and A in each case corresponds to a row of Tabfe C.
Table 791
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH=NOCH3, and
A in each case corresponds to a row of Table C.
Table 792
Compounds of the formula IA wherein Q1 denotes iodine. Q3 denotes CH=NOCH2CH.3:
and A in each case corresponds to a row of Table C.
Table 793
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH=NOCH(CH3)2
and A in each case corresponds to a row of Table C.
Table 794
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH=NOC(CH3)3,
and A in each case corresponds to a row of Table C.
Table 795
Compounds of the formula iA wherein Q1 denotes iodine, Q3 denotes C(CH3)=NOCH3,
and A in each case corresponds to a row of Table C.
Table 796
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes
C(CH3)=NOCH2CH3, and A in each case corresponds to a row of Table C.
Table 797
Compounds of the formula iA wherein Q1 denotes iodine, Q3 denotes
C(CH3)=NOCH(CH3)2, and A in each case corresponds to a row of Table C.
Table 798
Compounds of the formula iA wherein Q1 denotes iodine, Q3 denotes
C(CH3)=NOC(CH3)3, and A in each case corresponds to a row of Table C.
Table 799
Compounds of the formula !A wherein Q1 denotes cyano, Q3 denotes CF3l and A in
each case corresponds to a row of Table C.

102
Table 800
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes bromine, and A fn
each case corresponds to a row of Table C.
Table 801
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes chlorine, and A in
each case corresponds to a row of Table C,
Table 802
Compounds of the formula LA wherein Q1 denotes cyano, Q3 denotes CH3, and A in
each case corresponds to a row of Table C.
Table 803
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH3, and A in
each case corresponds to a row of Table C.
Table 804
Compounds of the formula iA wherein Q1 denotes cyano, Q3 denotes OCHCH2, and A
in each case corresponds to a row of Table C.
Table 805
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes ethoxy, and A in
each case corresponds to a row of Table C.
Table 806
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2CHFOCH3,
and A in each case corresponds to a row of Tabie C.
Table 807
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2CH=CH2,
and A in each case corresponds to a row of Table C.
Tabie 808
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2CCH, and
A in each case corresponds to a row of Table C.
Table 809
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2OCH3, and A
in each case corresponds to a row of Tabie C.
Table 810

103
Compounds of the formula IA wherein Q' denotes cyano, Q3 denotes CH2OCH2CH3,
and A .in each case corresponds to a row of Table C.
Table 811
Compounds of the formula [A wherein Q1 denotes cyano, Q3 denotes ChhSChb, and A
in each case corresponds to a row of Table C.
Table 812
Compounds of the formula !A wherein Q1 denotes cyano, Q3 denotes CH2SCH2CH3,
and A in each case corresponds to a row of Table C.
Table 813
Compounds of the formula lA wherein Q1 denotes cyano, Q3 denotes CH2S(=0)CH3,
and A in each case corresponds to a row of Table C.
Table 814
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes
CH2S(=0)CH2CH3, and A in each case corresponds to a row of Table C.
Table 815
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2S(=0)2CH3,
and A in each case corresponds to a row of Table C.
Table 816
Compounds of the formula iA wherein Q1 denotes cyano, Q3 denotes
CH2S(=0)2CH2CH3, and A in each case corresponds to a row of Table C.
Table 817
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes -OS(=0)2CH3,
and A in each case corresponds to a row of Table C.
Table 818 .
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes
-OS(=0)2CH2CH3, and A in each case corresponds to a row of Table C.
Table 819
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes
-OS(=0)2CH2CF3, and A in each case corresponds to a row of Table C,
Table 820
Compounds'of the formula IA wherein Q1 denotes cyano, Q3 denotes -OS(=0)2CCF2,
and A in each case corresponds to a row of Table C.

104
Table 821
Compounds of the formula (A wherein Q1 denotes cyano, G3 denotes OC(=0)CF3, and
A in each case corresponds to a row of Table C.
Table 822
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes NHCfi2CF3l and
A in each case corresponds to a row of Table C.
Table 823
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes
OChfe-cyclopropyf, and A in each case corresponds to a row of Table C.
Table 824
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2C(Ci)=CH2,
and A in each case corresponds to a row of Table C.
Table 825
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2CH=CF2,
and A in each case corresponds to a row of Table C.
Table 826
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes NHS(=0)2CF3,
and A in each case corresponds to a row of Table C.
Table 827
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes NHC{=0)CF3,
and A in each case corresponds to a row of Table C.
Table 828
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2CN, and A
in each case corresponds to a row of Table C,
Table 829
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2NO2, and A
in each case corresponds to a row of Table C.
Table 830
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes cyclopropyloxy,
and A in each case corresponds to a row of Table C.
Table 831

105
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2OCHF2, and
A in each case corresponds to a row of Table C.
Table 832
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2S(=0)2CHF2,
and A in each case corresponds to a row of Table C.
Table-833
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH=NOCH3, and
A in each case corresponds to a row of Table C.
Table 834
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH=NOCH2Ch'3,
and A in each case corresponds to a row of Table C.
Table 835
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH=NOCH(CH3)2
and A in each case corresponds to a row of Table C.
Table 836
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH=NOC(CH3)3,
and A in each case corresponds to a row of Table C.
Table 837
Compounds of the formula f A wherein Q1 denotes cyano, Q3 denotes C(CH3)=NOCH3,
and A in each case corresponds to a row of Table C.
Table 838
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes
C(CH3)=NOGH2CH3, and A in each case corresponds to a row of Table C.
Table 839
Compounds of the formula !A wherein Q1 denotes cyano, Q3 denotes
C(CH3)=NOCH(CH3)2) and A in each case corresponds to a row of Table C.
Table 840
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes
C(CH3)=NOC(CH3)3, and A in each case corresponds to a row of Table C.
Table 841
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CF3, and A in
each case corresponds to a row of Table C.

106
Table 842
Compounds of the formula [A wherein Q1 denotes methyl, Q3 denotes bromine, and A
in each case corresponds to a row of Table C.
Table 843
Compounds of the formula !A wherein Q1 denotes methyl, Q3 denotes chlorine, and A
in each case corresponds to a row of Table C,
Table 844
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH3> and A in
each case corresponds to a row of Table C.
Table 845
Compounds of the formula-1A wherein Q1 denotes methyl; Q3 denotes OCH3> and A in
each case corresponds to a row of Table C.
Table 846
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCHCH2, and A
in each case corresponds to a row of Table C.
Tabfe 847
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes ethoxy, and A in
each case corresponds to a row of Table C.
Table 848
Compounds of the formula fA wherein Q1 denotes methyl, Q3 denotes OCH2CHFOCH3,
and A in each case corresponds to a row of Table C.
Table 849
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2CH=CH2,
and A in each case corresponds to a row of Table C.
Table 850
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2CCH, and
A in each case corresponds to a row of Table C.
Table 851
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2OCH3, and A
in each case corresponds to a row of Table C,
Table 852

107
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2OCH2CH3,
and A in each case corresponds to a row of Table C.
Table 853
Compounds of the formula SA wherein Q1 denotes methyl, Q3 denotes CH2SCH3, and A
in each case corresponds to a row of Table C.
Table 854
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2SCH2CH3,
and A in each case corresponds to a row of Table C.
Table 855
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2S{=0)CH3,
and A in each case corresponds to a row of Table C,
Table 856
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes
CH2S(=0)CH2CH3, and A in each case corresponds to a row of Table C.
Table 857
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2S(=0)2CH3,
and A in each case corresponds to a row of Table C.
Table 858
Compounds of the formula iA wherein Q1 denotes methyl, Q3 denotes
CH2S(=0)2CH2CH3, and A in each case corresponds to a row of Table C,
Table 859
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes -OS(=0)2CH3,
and A in each case corresponds to a row of Table C.
Table 860
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes
-OS(=0)2CH2CH3, and A in each case corresponds to a row of Table C.
Table 861
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes
-OS(=0)2CH2CF3, and A in each case corresponds to a row of Table C.
Table 862
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes -OS(=0)2CCIF2,
and A in each case corresponds to a row of Table C,

108
Table 863
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OC(=0)CF3, and
A in each case corresponds to a row of Table C.
Table 864
ComnQunds of the formula IA wherein Q1 denotes methyl, Q3 denotes NHCH2CF3, and
A in each case corresponds to a row of Table C. .
Table 865
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes
OCHa-cyclopropyl, and A in each case corresponds to a row of Table C.
Table 866
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2C(CI)=CH2,
and A in each case corresponds to a row of Table C.
Table 867
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2CH=CF2,
and A in each case corresponds to a row of Table C.
Table 868
Compounds of the formula !A wherein Q1 denotes methyl, Q3 denotes NHS(=0)2CF3,
and A in each case corresponds to a row of Table C,
Table 869
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes NHC(=0)CF3,
and A in each case corresponds to a row of Table C.
Table 870
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2CN, and A
in each case corresponds to a row of Table C.
Table 871
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2NO2, and
A in each case corresponds to a row of Table C.
Table 872
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes cyclopropyloxy,
and A in each case corresponds to a row of Table C.
Table 873

109
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2OCHF2, and
A in each case corresponds to a row of Table C.
Table 874'.
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2S(=0)2CHF2,
and A in each case corresponds to a row of Table C.
Table 875
Compounds of the formula IA wherein Q1 denotes methyl, G3 denotes CH=NOCH3, and
A in each case corresponds to a row of Table C.
Table 876
Compounds of the formula IA wherein Q1 denotes methy!, Q3 denotes CH=NOCH2CH3,
and A in each case corresponds to a row of Table C,
Table 877
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes
CH=NOCH(CH3)2and A in each case corresponds to a row of Table C.
Table 878 '
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH=NOC(CH3)3,
and A in each case corresponds to a row of Table C.
Table 879
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes C(CH3)=NOCH3,
and A in each case corresponds to a row of Table C,
Table 880
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes
C(CH3)-NOCH2CH3, and A in each case corresponds to a row of Table C.
Table 881
Compounds of the formula !A wherein Q1 denotes methyl, Q3 denotes
C(CH3)=NOCH(CH3)2, and A in each case corresponds to a row of Table C.
Table 882
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes
C(CH3)=NOC(CH3)3, and A in each case corresponds to a row of Table C.

110


111


112


113-


114


115


116


117


118


119


120


121


122


123


124


125


126


127


128


129


130


131


132


133


134


135


136


137


138


1.39


140 -


141


142


143


144


145


146



147
Table 883
Compounds of the formula IA (as defined above) wherein Q1 denotes hydrogen, Q3
denotes CF3, and A In each case corresponds to a radical of Tab!e D.
Table 884
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes bromine, and
A in each case corresponds to a radical of Table D.
Table 885
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes chlorine, and
A in each case corresponds to a radical of Table D.
Table 886 >
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH3, and A in
each case corresponds to a radical of Table D.
Table 887
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH3, and A
in each case corresponds to a radical of Table D.
Table 888
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCHCH2, and
A in each case corresponds to a radical of Table D,
Table 889 . .

148
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes ethoxy, and A
in each case corresponds to a radical of Table D.
Table 890
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
OCH2CHFOCH3, and A in each case corresponds to a radical of Table D.
Table 891
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
OCHfeCHChb, and A in each case corresponds to a radical of Tabie D.
Table 892
Compounds of the formula IA wherein Q1 denotes hydrogen, G3 denotes OCH2CCH,
and A in each case corresponds to a radical of Table D.
Table 893
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2OCH3,
and A in each case corresponds to a radical of Table D.
Tabie 894 .
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
CH2OCH2CH3, and A in each case corresponds to a radical-of Table D,
Table 895
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2SCH3,
and A in each case corresponds to a radical of Table D.
Table 896
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes ChkSChCHs,
and A in each case corresponds to a radical of Table D.
Table 897
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
CH2S(=0)CH3, and A in each case corresponds to a radical of Table D.
Table 898
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
CH2S(=0)CH2CH3, and A in each case corresponds to a radical of Tabie D.
Table 899
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
CH2S(=0)2CH3, and A in each case corresponds to a radical of Table D.

149
Table 900
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
CH2S(=0)2CH2CH3, and A in each case corresponds to a radical of Table D.
Table 901
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes -OS(=0}2CH3J
and A in each case corresponds to a radical of Table D.
Table 902
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
-OSiOCrbCHs, and A in each case corresponds to a radical of Table D.
Table 903
Compounds of the formula !A wherein Q1 denotes hydrogen, Q3 denotes
-OS(=0)2CH2CF3, and A In each case corresponds to a radical of Table D.
Table 904
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
-OS(=0)2CCiF2, and A in each case corresponds to a radical of Table D.
Table 905
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OC(=0)CF3,
and A in each case corresponds to a radical of Table D.
Table 906
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes NHCH2CF3,
and A in each case corresponds to a radical of Table D.
Table 907
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
OCH2-cyc!opropyl, and A in each case corresponds to a radical of Table D.
Table 908
Compounds of the formula iA wherein Q1 denotes hydrogen, Q3 denotes
OCH2C(CI)=CH2, and A in each case corresponds to a radical of Table D.
Table 909
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
OCH2CH=CF2, and A in each case corresponds to a radical of Table D.

150
Table 910
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
NHS(=0)2CF3, and A in each case corresponds to a radical of Table D.
Table 91.1
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes NHC(=0)CF3,
and A In each case corresponds to a radical of Table D.
Table 912
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH2CN, and
A in each case corresponds to a radical of Table D.
Table 913
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes OCH2NO2,
and A in each case corresponds to a radical of Table D,
Table 914
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes cyclopropy-
loxy, and A in each case corresponds to a radical of Table D.
Table 915
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes CH2OCHF2,
and A in each case corresponds to a radical of Table D.
Table 916
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
CH2S(=0)2CHF2, and A in each case corresponds to a radical of Table D.
Table 917
Compounds of the formula lA wherein Q1 denotes hydrogen, Q3 denotes CH-NOCH3,
and A in each case corresponds to a radical of Table D.
Table 918
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
CH=NOCH2CH3, and A in each case corresponds to a radical of Table D.
Table 919
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
CH=NOCH(CH3)2and A in each case corresponds to a radical of Table D,
Table 920

151
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
CH=NOC(CH3)3, and A in each case corresponds to a radical of Table D.
Table 921
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
C(CH3)=NOCH3, and A in each case corresponds to a radical of Table D.
Table 922
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
C(CH3)=NOCH2Ch'3! and A in each case corresponds to a radical of Tabie D.
Table 923
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
C{CH3)=NOCH(CH3)2, and A In each case corresponds to a radical of Table D,
Table 924
Compounds of the formula IA wherein Q1 denotes hydrogen, Q3 denotes
C(CH3)=NOC(CH3)3, and A in each case corresponds to a radical of Table D.
Tabie 925
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CF3) and A in
each case corresponds to a radical of Table D.
Table 926
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes bromine, and A
in each case corresponds to a radical of Table D.
Table 927
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes chlorine, and A
in each case corresponds to a radical of Table D.
Table 928
Compounds of the formula IA wherein Q* denotes chlorine, Q3 denotes CH3, and A in
each case corresponds to a radical of Table D.
Tabie 929
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH3, and A in
each case corresponds to a radical of Table D.
Table 930
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCHCH2, and
A in each case corresponds to a radical of Table D.

152
Table 931
Compounds of the formula SA wherein Q1 denotes chlorine, Q3 denotes ethoxy, and A
in each case corresponds to a radical of Table D.
Table 932
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
OCH2CHFOCH3, and A in each case corresponds to a radical of Table D.
Table 933
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2CH=CH2,
and A in each case corresponds to a radical of Table D.
Table 934
Compounds of the formula (A wherein Q1 denotes chlorine, Q3 denotes OCH2CCH, and
A in each case corresponds to a radical of Table D.
Table 935
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2OCH3, and
A in each case corresponds to a radical of Table D.
Table 936
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2OCH2CH3,
and A in each case corresponds to a radical of Table D.
Table 937
Compounds of the formula !A wherein Q1 denotes chlorine, Q3 denotes CH2SCH3, and
A in each case corresponds to a radical of Table D.
Table 938
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2SCH2CH3,
and A in each case corresponds to a radical of Table D.
Table 939
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2S(=0)CH3,
and A in each case corresponds to a radical of Table D.
Table 940
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
CH2S(=0)CH2CH3, and A in each case corresponds to a radical of Table D.
Table 941

153
Compounds of the formula !A wherein Q1 denotes chlorine, Q3 denotes CH2S(=0)2CH3,
and A in each case corresponds to a radical of Table D.
Table 942
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
CH2S(=0)2CH2CH3, and A in each case corresponds to a radical of Table D.
Table 943
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes -OS(=0)2CH3,
and A in each case corresponds to.a radical of Table D.
i «uiv vf-r-r
Compounds of the formula ! A wherein Q1 denotes chlorine, Q3 denotes
-OS(-0)2CH2CH3, and A in each case corresponds to a radica! of Table D,
f abie 945
Compounds of the formula !A wherein Q1 denotes chlorine, Q3 denotes
-OS(=0)2CH2CF3j and A in each case corresponds to a radical of Table D.
Table 946
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
-OS(=0)2CCIF2, and A in each case corresponds to a radical of Tabie D.
Table 947
Compounds of-the formula IA wherein Q1 denotes chlorine, Q3 denotes OC(=0)CF3,
and A m each case corresponds to a radical of Table D,
Table 948
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes NHCH2CF3,
and A in each case corresponds to a radical of Table D.
Table 949
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
OCH2-cycIopropyi, and A in each case corresponds to a radical of Table D.
Table 950
Compounds: of the formula IA wherein Q1 denotes chlorine, Q3 denotes
OCH2C(C!)=CH2, and A in each case corresponds to a radical of Table D.
Table 951
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2CH=CF2t
and A in each case corresponds to a radical of Table D.

154
Table 952
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 'denotes NHS(=0)2CF3l
and A in each case corresponds to a radical of Table D.
Table 953
Compounds of the formula JA wherein Q1 denotes chiohne, Q3 denotes NHC(=0)CF3,
and A in each case corresponds to a radical of Table D.
Table 954
Compounds of the formula !A wherein Q1 denotes chlorine, Q3 denotes OCH2CN, and
A in each case corresponds to a radical of Table D.
Tabie 955
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes OCH2NO2, and
A in each case corresponds to a radical of Tabie D.
Table 956
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes cyclopropyloxy,
and A in each case corresponds to a radical of Table D.
Table 957
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH2OCHF2,
and A in each case corresponds to a radical of Table D.
Table 958
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
CH2S(=0)2CHF2, and A in each case corresponds to a radical of Table D.
Table 959
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes CH=NOCH3,
and A in each case corresponds to a radical of Table D.
Table 960
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
CH=NOCH2CH3> and A in each case corresponds to a radical of Tabie D.
Table 961
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
CH=NOCH(CH3)2 and A in each case corresponds to a radical of Table D,
Table 962

155
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
CH=NOC(CH3)3, and A in each case corresponds to a radical of Table D.
Table 963 .
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
C(CH3)=NOCH3, and A in each case corresponds to a radical of Table D.
Tabfe 964
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
C(CH3)=NOCH2CH3, and A in each case corresponds to a radical of Tabie D.
Compounds of the formula !A wherein Q1 denotes chlorine, Q3 denotes
C(CH3)=NOCH(CH3)2, and A in each case corresponds to a radicaf of Table D.
Tabie 966
Compounds of the formula IA wherein Q1 denotes chlorine, Q3 denotes
C(CH3)=NOC(CH3)3, and A in each case corresponds to a radical of Table D.
Table 967
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CF3, and A in
each case corresponds to a radical of Table D.
Tabie 968
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes bromine, and A
in each case corresponds to a radical of Table D.
Table 969
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes chlorine, and A
in each case corresponds to a radical of Tabie D.
Table 970
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH3, and A in
each case corresponds to a radical of Table D.
Table 971
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH3, and A in
each case corresponds to a radical of Table D.
Table 972
Compounds of the formula IA wherein Q1 .denotes bromine, Q3 denotes OCHCH2, and
A in each case corresponds to a radical of Table D.

156
Table 973
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes ethoxy, and A
in each case corresponds to a radical of Table D.
Table 974
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
OCH2CHFOCH3, and A in each case corresponds to a radical of Table D.
Table 975
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2CH-CH2,
and A in each case corresponds to a radical of Table D.
Table 976
Compounds of the formuia LA wherein G1 denotes bromine, G3 denotes OCH2CCH,
and A in each case corresponds to a radical of Table D.
Table 977
Compounds of the formuia IA wherein Q1 denotes bromine, Q3 denotes CH2OCH3, and
A in each case corresponds to a radical of Table D.
Table 978
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2OCH2CH3,
and A in each case corresponds to a radical of Table D.
Table 979
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2SCH3, and
A in each case corresponds to a radical of Table D.
Table 980
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2SCH2CH3,
and A in each case corresponds to a radical of Table D.
Table 981
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2S(=0)CH3,
and A in each case corresponds to a radical of Table D.
Table 982
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
CH2S(=0)CH2CH3l and A in each case corresponds to a radical of Table D.
Table 983

157
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2S(=0}2CH3,
and A in each case corresponds to a radical of Table D.
Table 984
Compounds of the formula iA wherein Q1 denotes bromine, Q3 denotes
CH2S(=0)2CH2CH3, and A in each case corresponds to a radical of Table D.
Table 985
Compounds of the formula SA wherein Q1 denotes bromine, Q3 denotes -OS(=0)2CH3,
and A in each case corresponds to a radical of Table D.
ToK! nac
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
-OS(=0)2CH2CH3, and A in each case corresponds to a radical of Tabie D.
Table 987
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
-OS(=0)2CH2CF3> and A in each case corresponds to a radical of Table D.
Table 988
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
-OS(=0)2CCIF2, and A in each case corresponds to a radical of Table D.
Table 989
Compounds of the formula.IA wherein Q1 denotes bromine, Q3 denotes OC(=0)CF3,
and A in each case corresponds to a radical of Tabie D.
Table 990
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes NHCH2CF3,
and A in each case corresponds to a radical of Table D.
Table 991
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
OCFb-cyclopropyl, and A in each case corresponds to a radical of Table D.
Table 992
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
OCH2C(CI)=CH2, and A in each case corresponds to a radical of Table D.
Table 993
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2CH=CF2,
and A in each case corresponds to a radical of Table D.

158
Table 994
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes NHS(=0)2CF3f
and A in each case corresponds to a radical of Table D.
Table 995
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes NHC(=0)CF3,
and A in each case corresponds to a radical of Table D.
Table 996
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OChbCN, and
A in each case corresponds to a radicai of Table D.
Table 997
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes OCH2NO2, and
A in each case corresponds to a radical of Table D.
Table 998
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes cyclopropyloxy,
and A in each case corresponds to a radicai of Table D.
Table 999
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH2OCHF2,
and A in each case corresponds to a radicai of Table D.
Table 1000
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
CH2S(=0)2CHF2, and A in each case corresponds to a radicai of Table D.
Table 1001
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes CH=NOCH3,
and A in each case corresponds to a radical of Table D.
Table 1002
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
CH=NOCH2CH3, and A in each case corresponds to a radicai of Table D.
Table 1003
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
CH=NOCH(CH3)2and A in each case corresponds to a radical of Table D.
Table 1004

159
Compounds of the formula IA wherein Q1 denotes bromine,. Q3 denotes
CH=NOC{CH3)3, and A in each case corresponds to a radical of Table p.
Table 1005
Compounds of the formula !A wherein Q1 denotes bromine, Q3 denotes
C(CH3)=NOCH3] and A in each case corresponds to a radical of Table D,
Tabie i 006
Compounds of the formula IA wherein Q1 denotes bromine, Q3 denotes
C(CH3)=NOCH2CH3, and A in each case corresponds to a radical of Table D,
Table 1007
Compounds of the formuia IA wherein Q1 denotes bromine, Q3 denotes
C(CH3)=NOCH(CH3}2, and A in each case corresponds to a radical of Table D.
Table 1008
Compounds of the formula [A wherein Q1 denotes bromine, Q3 denotes
C(CH3)=NOC(CH3)3, and A in each case corresponds to a radical of Table D.
Table 1009
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CF3, and A in
each case corresponds to a radical of Table D.
Table 1010
Compounds of the formula IA wherein Q1 denotes fluorine, G3 denotes bromine, and A
in each case corresponds to a radical of Table D.
Table 1011
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes chlorine, and A
in each case corresponds to a radical of Table D.
Table 1012
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH3, and A in
each case corresponds to a radical of Table D.
Table 1013
Compounds of the formuia IA wherein Q1 denotes fluorine, Q3 denotes OCH3, and A in
each case corresponds to a radical of Table D.
Table 1014
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCHCH2, and A
in each case corresponds to a radical of Table D.

160
Table 1015
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes ethoxy, and A in
each case corresponds to a radical of Table D.
Table 1016
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
OCH2CHFOCH3, and A in each case corresponds to a radical of Table D.
Table.1017
Compounds of the formula !A wherein Q1 denotes fluorine, Q3 denotes OCH2CH=CH2,
and A in each, case corresponds to a radical of >. 3uiS u.
Table 1018
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH2CCH, and
A in each case corresponds to a radical of Table D.
Table 1019
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2OCH3, and
A in each case corresponds to a radical of Table D.
Table 1020
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2OCH2CH3,
and A in each case corresponds to a radical of Table D.
Table 1021
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2SCH3, and
A in each case corresponds to a radical of Table D.
Table 1022
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2SCH2CH3l
and A in each case corresponds to a radical of Table D.
Table 1023
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2S(=0)CH3,
and A in each case corresponds to a radical of Table D.
Table 1024
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
CH2S(=0)CH2CH3, and A in each case corresponds to a radical of Table D.
Table 1025

161
Compounds of the formula lA wherein Q1 denotes fluorine, Q3 denotes CH2S(=0}2CH3,
and A in each case corresponds to a radical of Table D.
Table 1026
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
CH2S{=0)2CH2C!-k and A in each case corresponds to a radical of Table D.
Table 1027
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes -OS(=0)zCH3,
and A in each case corresponds to a radical of Table D.
Table 1028
Compounds of the formula iA wherein Q1 denotes fluorine, Q3 denotes
-0S(=O)2CH2CH3, and A in each case corresponds to a radical of Table D.
Table 1029
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
-OS(=0)2CH2CF3, and A in each case corresponds to a radical of Table D.
Table 1030
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes -OS(=0)2CCIF2,
and A in each case corresponds to a radical of Table D.
Table 1031
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OC(=0)CF3>
and A in each case corresponds to a radical of Table D.
Table 1032
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes NHCH2CF3, and
A in each case corresponds to a radical of Table D.
Table 1033
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
OCH2-cyclopropyl, and A in each case corresponds to a radical of Table D.
Table 1034
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
OCH2C(Ci)=CH2, and A in each case corresponds to a radical of Table D.
Table 1035
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH2CH=CF2,
and A in each case corresponds to a radical of Table D.

162
Table 1036
Compounds of the formula SA wherein Q1 denotes fluorine, Q3 denotes NHS(=0)2CF3,
and A in each case corresponds to a radical of Table D.
Table 1037
Compounds of the formula IA wherein G'> denotes fluorine, Q3 denotes NHC(=0)CF3,
and A in each case corresponds to a radical of Table D.
Table 103S
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH2CN, and A
In each case corresponds to a radical of Table D,
Table 1039
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes OCH2N02, and
A in each case corresponds to a radical of Table D.
Table 1040
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes cyclopropyloxy,
and A in each case corresponds to a radical of Table D.
Table 1041
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH2OCHF2, and
A in each case corresponds to a radical of Table D.
Table 1042
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
CH2S(=0)2CHF2, and A in each case corresponds to a radical of Table D.
Table 1043
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes CH=NOCH3,
and A in each case corresponds to a radical of Table D.
Table 1044
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
CH=NOCH2CH3> and A in each case corresponds to a radical of Table D.
Table 1045
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
CH=NOCH(CH3)2 and A in each case corresponds to a radical of Table D.
Table 1046

163
Compounds of the formula !A wherein Q1 denotes fluorine, Q3 denotes
CH=NOC(CH3)3, and A in each case corresponds to a radical of Table D.
Table 1047
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
C(CH3)=NOCH3, and A in each case corresponds to a radical of Table D.
Table 1048
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
C(CH3)=NOCH2CH3, and A in each case corresponds to a radical of Table D.
Table 1049
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
C(CH3)=NOCH(CH3)2, and A in each case corresponds to a radical of Table D.
Table 1050
Compounds of the formula IA wherein Q1 denotes fluorine, Q3 denotes
C(CH3)=NOC(CH3)3, and A in each case corresponds to a radical of Table D.
Table 1051
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CF3, and A in
each case corresponds to a radical of Table D.
Table 1052
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes bromine, and A in
each case corresponds to a radical of Table D.
Table 1053
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes chlorine, and A in
each case corresponds to a radical of Table D.
Table 1054
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH3, and A in
each case corresponds to a radical of Table D.
Table 1055
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH3l and A in
each case corresponds to a radical of Table D.
Table 1056
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCHCH2, and A
in each case corresponds to a radical of Table D.

164
Table 1057
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes ethoxy, and A in
each case corresponds to a radical of Table D.
Table 1058
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2CHFOCH3,
and A in each case corresponds to a radical of Table D.
Table 1059
Compounds of the formula [A wherein Q1 denotes iodine, Q3 denotes OCH2CH=CH2,
and A in each case corresponds to a radical of Table D.
Table 1060
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2CCH, and
A in each case corresponds to a radical of Table D,
Table 1061
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes ChbOCHs, and A
in each case corresponds to a radical of Table D.
Table 1062
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2OCH2CH3,
and A in each case corresponds to a radical of Table D.
Table 1063
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2SCH3, and A
in each case corresponds to a radical of Table D.
Table 1064
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2SCH2CH3,
and A in each case corresponds to a radical of Table D.
Table 1065
Compounds of the formula IA wherein Q' denotes iodine, Q3 denotes CH2S(=0)CH3,
and A in each case corresponds to a radical of Table D.
Table 1066
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes
CH2S(=0)CH2CH3, and A in each case corresponds to a radical of Table D.
Table 1067

165
Compounds of the formula IA wherein Q1.denotes iodine, Q3 denotes CH2S(=0)2CH3,
and A in each case corresponds to a radical of Table D.
Table 1068
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes
CH2S(=0)2CH2CH3, and A in each case corresponds.to a radical of Table D.
Table 1069
Compounds of the formula iA wherein Q1 denotes iodine. Q3 denotes -OS(=0)2CH3,
and A in. each case corresponds to a radical of Tabie D.
1 QUI? I U I U
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes
-OS(=0}2CH2CH3, and A in each case corresponds to a radical of Table D.
Table 1071
Compounds of the formula IA wherein Q1 denotes iodine, G3 denotes
-OS(=0)2CH2CF3, and A in each case corresponds to a radical of Table D,
Table 1072
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes -OS(=0)2CCIF2,
and A in each case corresponds to a radical of Tabie D.
Table 1073
Compounds of the formula !A wherein Q1 denotes iodine, Q3 denotes OC(=0)CF3, and
A in each case corresponds to a radical of Table D.
Table 1074
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes NHCH2CF3, and
A in each case corresponds to a radical of Table D.
Table 1075
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes
OCH2-cyclopropyl, and A in each case corresponds to a radical of Table D.
Table 1076
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2C(CI)=CH2,
and A in each case corresponds to a radical of Tabie D.
Table 1077
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2CH=CF2,
and A in each case corresponds to a radical of Table D.

166
Table 1078
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes NHS(=0)2CF3,
and A in each case corresponds to a radical of Table D.
Table 1079
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes NHC(=0)CF3,
and A. in each case corresponds to a radical of Table D.
Table 1080
Compounds of the formula !A wherein Q1 denotes iodine, Q3 denotes OCH2CN, and A
Table 1081
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes OCH2NO2, and A
in each case corresponds to a radical of Table D.
Table 1082
Compounds of the formuia IA wherein Q1 denotes iodine, Q3 denotes cyclopropyioxy,
and A in each case corresponds to a radical of Table D.
Table 1083
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2OCHF2, and
A in each case corresponds to a radical of Table D.
Table 1084
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH2S(=0)2CHF2j
and A in each case corresponds to a radical of Table D.
Table 1085
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH=NOCH3) and
A in each case corresponds to a radical of Table D.
Table 1086
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH=NOCH2CH3l
and A in each case corresponds to a radical of Table D.
Table 1087
Compounds of the formuia IA wherein Q1 denotes iodine, Q3 denotes CH=NOCH(CH3)2
and A in each case corresponds to a radical of Table D.
Table 1088

167
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes CH=NOC(CH3)3,
and A in each case corresponds to a radical of Table D.
Table 1089
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes C(CH3)=NOCH3,
and A in each case corresponds to a radical of Table D.
Table 1090
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes
C(CH3)=NOCH2CH3, and A in each case corresponds to a radical of Table D.
Table 1091
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes
. C(CH3)=NOCH(CH3)2, and A in each case corresponds to a radical of Table D.
Table 1092
Compounds of the formula IA wherein Q1 denotes iodine, Q3 denotes
C(CH3)=NOC(CH3)3, and A in each case corresponds to a radical of Table D.
Table 1093
Compounds of the formula ! A wherein Q1 denotes cyano, Q3 denotes CF3, and A in
each case corresponds to a radical of Table D.
Table 1094
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes bromine, and A in
each case corresponds to a radical of Table D.
Table 1095
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes chlorine, and A in
each case corresponds to a radical of Table D.
Table 1096
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH3, and A in
each case corresponds to a radical of Table D.
Table 1097
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH3i and A in
each case corresponds to a radical of Table D.
Table 1098
Compounds of the formula fA wherein Q1 denotes cyano, G3 denotes OCHCH2, and A
in each case corresponds to a radical of Table D.

168
Table 1099
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes ethoxy, and A in
each case corresponds to a radical of Table D.
Table 1100
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2CHFOCH3,
and A in each case corresponds to a radical of Table D.
Table 1101
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2CH=CH2,
and A. In each case corresponds to a radical of Table D.
Table 1102
Compounds of the formula iA wherein Q1 denotes cyano, Q3 denotes OCH2CCH, and
A in each case corresponds to a radical of Table D.
Table 1103
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2OCH3, and A
in each case corresponds to a radical of Table D.
Table 1104
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2OCH2CH3,
and A in each case corresponds to a radical of Table D.
Table 1105
Compounds of the formula !A wherein Q1 denotes cyano, Q3 denotes CH2SCH3, and A
in each case corresponds to a radical of Table D.
Table 1106
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2SCH2CH3,
and A in each case corresponds to a radical of Table D.
Table 1107
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2S(=0)CH3,
and A in each case corresponds to a radical of Table D.
Table 1108
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes
CH2S(=G)CH2CH3, and A in each case corresponds to a radical of Table D.
Table 1109

169
Compounds of the formula !A wherein Q1 denotes cyano, Q3 denotes CH2S(=0)2CH3,
and A in each case corresponds to a radical of Table D.
Table 111.0
Compounds of the formula IA wherein Q1 denotes cyan.o, Q3 denotes
CH2S(=Q)2CH2CH3, and A in each case corresponds to a radical of Table. D.
Table 1111
Compounds'of the formula IA wherein Q1 denotes cyano, Q3 denotes -OSOCHs,
and A in each case corresponds to a radical of Table D.
Tabie 1112
Compounds of the formula iA wherein Q1 denotes cyano, Q3 denotes
-OS(=0)2CH2CH3i and A in each case corresponds to a radical of Table D.
Table 1113
Compounds of the formula !A wherein Q1 denotes cyano, Q3 denotes
-OS(=0)2CH2CF3, and A in each case corresponds to a radical of Table D.
Tabie 1114
Compounds of the formula !A wherein Q1 denotes cyano, Q3 denotes -0S(=0)2CCIF2,
and A in each case corresponds to a radical of Table D.
Table 1115
Compounds of the formula (A wherein Q1 denotes cyano, Q3 denotes OC(=0)CF3, and
A in each case corresponds to a radical of Table D.
Table 1116
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes NHCH2CF3, and
A in each case corresponds to a radical of Table D,
Table 1117
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes
OCH2-cyclopropyi, and A in each case corresponds to a radical of Table D.
Table 1118
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2C(C!)=CH2l
and A in each case corresponds to a radical of Table D.
Table 1119
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes OCH2CH=CF2,
and A in each case corresponds to a radical of Table D.

170
Table 1120
Compounds of the formula iA wherein Q1.denotes cyano, Q3 denotes NHS(=0)2CF3,
and A in each-case corresponds to a radical of Table D.
Table 1121 ' "" '
Compounds of the formula iA wherein Q1 denotes cyano, Q3 denotes NHC(=0)CF3,
and A jn each case corresponds to a radical of Table D.
Table 1122
Compounds of the formula ! A wherein Q1 denotes cyano, Q3 denotes OCH2CN, and A
in each case corrssoonds to 3 radical of Table D.
Table 1123
Compounds of the formula IA wherein Q1 denotes cyano, G3 denotes OCH2NO2, and A
in each case corresponds to a radical of Table D.
Table 1124
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes cyclopropyloxy,
and A in each case corresponds to a radical of Table D.
Table 1125
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2OCHF2, and
A in each case corresponds to a radical of Table D.
Table 1126
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH2S{=0)2CHF2,
and A in each case corresponds to a radical of Table D.
Table 1127
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH=NOCH3, and
A in each case corresponds to a radical of Table D.
Table 1128
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH=NOCH2CH3,
and A in each case corresponds to a radical of Table D.
Table 1129
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes CH=NOCH(CH3)2
and A in each case corresponds to a radical of Table D.
Table 1130

171
Compounds of the formula IA wherein Q1 denotes cyano, G3 denotes CH=NOC{CH3)3,
and A in each case corresponds to a radical of Table D.
Table 1131
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes C(CH3)=NOCH3,
and A in each case corresponds to a radical of Table D.
Table '1132
Compounds of the formula IA wherein Q1 denotes cyano, Q3 denotes
C(CH3)=NOCH2CH3, and A in each case corresponds to a radical of Table D.
Table 1133
Compounds of the formula (A wherein Q1 denotes cyano, Q3 denotes
C{CH3)=NOCH(CH3)2, and A in each case corresponds to a radical of Table D.
Table 1134
Compounds of the formula iA wherein Q1 denotes cyano, Q3 denotes
C(CH3)=NOC(CH3)3, and A in each case corresponds to a radical of Table D.
Table 1135
Compounds of the formula !A wherein Q1 denotes methyl, Q3 denotes CF3, and A in
each case corresponds to a radical of Table D.
Table 1136
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes bromine, and A
in each case corresponds to a radical of Table D.
Table 1137
Compounds of the formula iA wherein Q1 denotes methyl, Q3 denotes chlorine, and A
in each case corresponds to a radical of Table D.
Table 1138
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH3, and A in
each case corresponds to a radical of Table D.
Table 1139
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH3, and A in
each case corresponds to a radical of Table D.
Table .1140
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCHCH2, and A
in each case corresponds, to a radical of Table D.

172
Table. 1141
Compounds of the formula fA wherein Q1 denotes methyl, Q3 denotes ethoxy, and A in
each case corresponds to a radical of Table D.
Table 1142
Compounds of the formula !A wherein Q1 denotes methyl, Q3 denotes OCH2CHFOCH3,
and A in each case corresponds to a radical of Table D.
Table 1143
Compounds of the formuia IA wherein Q1 denotes methyl, Q3 denotes OCH2CH=CH2,
and A in each case corresponds n 3 rsi-fir-ai of TaMe D.
Table 1144
Compounds of the formuia IA wherein Q1 denotes methyl, Q3 denotes OCH2CCH, and
A in each case corresponds to a radical of Tab!e D.
Table 1145
Compounds of the formuia IA wherein Q1 denotes methyl, Q3 denotes CH2OCH3, and A
in each case corresponds to a radical of Table D.
Table 1146
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes ChbOChbCHs,
and A in each case corresponds to a radical of Table D.
Table 1147
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2SCH3, and A
in each case corresponds to a radical of Table D.
Table 1148
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2SCH2CH3,
and A in each case corresponds to a radical of Table D.
Table 1149
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2S(=0)CH3,
and A in each case corresponds to a radical of Table D.
Table 1150
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes
CH2S(=0)CH2CH3, and A in each case corresponds to a radical of Table D.
Table 1151

173
.Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2S(=0)2CH3,
and A in each case corresponds to a radical of Table D.
Table 11.52
Compounds of the formula IA wherein Q1 denotes methyl,. G3 denotes
CH2S(=0)2CH2CH3, and A in each case corresponds to a radical of Table D.
Table 1153
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes -OS{=0)2CH3,
and A in each case corresponds to a radical of Table D.
Table 1154
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes
-OS(=0}2CH2CH3, and A in each case corresponds to a radical of Table D.
Table 1155
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes
-OS(=0)2CH2CF3, and A in each case corresponds to a radical of Table D.
Table 1156
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes -OS(=0)2CCifr2,
and A in each case corresponds to a radical of Table D,
Table 1157
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OC(=0)CF3, and
A in each case corresponds to a radical of Table D,
Table 1158
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes NHCH2CF3, and
A in each case corresponds to a radical of Table D.
Table 1159
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes
OChb-cyclopropyl, and A in each case corresponds to a radical of Table D.
Table 1160
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2C(CI)=CH2,
and A in each case corresponds to a radical of Table D.
Table 1161
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2CS-NCF2,
and A in each case corresponds to a radical of Table D.

174
Table 1162
Compounds of the formula f A wherein Q1 denotes methyl, Q3 denotes NHS(=0)2CF3]
and A in each case corresponds to a radical of Table D..
Table 1163
Compounds of the formula !A wherein Q1 denotes methyl, Q3 denotes NHC(-0)CF3,
and A in each case corresponds to a radical of Tabie D.
Table 1164
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes OCH2CN, and A
in each case corresponds to a radical of Tabie D.
Table 1165
Compounds of the formula lA wherein Q1 denotes methyl, Q3 denotes OCH2NO2, and
A in each case corresponds to a radical of Table D.
Table 1166
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes cyclopropyloxy,
and A in each case corresponds to a radical of Table D.
Table 1167
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH2OCHF2, and
A in each case corresponds to a radical of Table D.
Table 1168
Compounds of the formula !A wherein Q1 denotes methyl, Q3 denotes CH2S{=0)2CHF2,
and A in each case corresponds to a radical of Table D.
Table 1169
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH=NOCH3, and
A in each case corresponds to a radical of Table D.
Tabie 1170
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH=NOCH2CH3,
and A in each case corresponds to a radical of Table D.
Table 1171
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes
CH=NOCH(CH3)2and A in each case corresponds to a radical of Table D.
Table 1172

175
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes CH=NOC(CH3);
and A in each case corresponds to a radical of Table D.
Table 1173
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes C(CH3)=NOCH;
and A in each case corresponds to a radical of Table D.
Table 1174
Compounds of the formula ! A wherein Q1 denotes methyl, Q3 denotes
C(CH3)=NOCH2CH3) and A in each case corresponds to a radical of Table D.
Table 1175
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes
C(CH3)=NOGH(GH3)2, and A in each case corresponds to a radical of Table D.
Table 1176
Compounds of the formula IA wherein Q1 denotes methyl, Q3 denotes
C(CH3)=NOC(CH3)3, and A in each case corresponds to a radical of Table D.
Table D: selected radicals A


176
The compounds of the formula I are.especially suitable for efficiently combating the
following pests:
insects from the order"of the lepidopterans (Lepidoptera), for example Agrotis ypsilon,
Agrotis segetum, Alabama argiilacea, Anticarsia gemmatalis, Argyresthia conjugella,
Autograph a gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheima-
tobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirpbis
unipuncta, Cydia pomonella, Dendrolimus p/ni, Diaphania nitidalis, Diatraea grandi-
ose/fa, Ear/as insulana, Elasmopalpus lignoselius, Eupoeciiia ambiguella, Evetria bou-
liana, Feltia subterranea, Galieria mei/onelia,. Grapholitha funebrana, Grapholitha mo-
lesta, Heliothis armigera, HeJiothis virescens, Heliothis zea, Heiiula undalis, Hibernia
defoliaria, Hyphantria cunea, Hyponomeuta mallnellus, Ksiferia lycopersiceiia, iamb-
dina fisceiiaria, Laphygma exigua, Leucopfera coffeeiia, Leucoptsra sciteiia, Lithocol-
fetis blancardella, Lobes/a botrana, Loxostege sticticalis,Lymantria dispar, Lymantria
monacha, Lyoneiia clerkella, Malacosoma neustria, Mamesira brassicae, Orgyia pseu-
dotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma
saucia, Phalera bucephala, Phfhorimaea operculelia, Phyllocnistis citrella, Pieris bras-
sicae, Plathypena scabra, Plutelia xyfostella, Pseudoplusia includens, Rhyacionia frus-
trana, Scrobipalpula absoluta, Sifotroga cerea/ella, Sparganothis pilleriana, Spodoptera
frugiperda, Spodoptera iittoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix
vlridana, Trichoplusia /7/'and Zeiraphera canadensis,
beetles (Co/eopfera), for example Agrilus sinuatus, Agriotes Uneatus, Agriotes obscu-
rus, Amphimallus soistitiaiis, Anisandrus dispar, Anthonomus grandis, Anthonomus
pomorum, Aphthona euphoridae, Athous haemorrhoidalis, Atomaria linearis, Bfasto-
phagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus
ientis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Cetonia aurata,
Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema tibialis, Conoderus
vespertinus, Crioceris asparagi, Ctenicera ssp., Diabrotica longicornis, Diabrotica
semipunctata, Diabrotica 12-punctata Diabrotica speciosa, Diabrotica virgifera, Epila-'
chna varivestis, Epitrix hirtipennis, Eutinobothrus brasitiensis, Hylobius abietis, Hypera
brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus,
Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus
communis, Meligethes aeneus, Meioiontha hippocastani, Melolontha melolontha,
Oulema oryzae, Ortiorrhynchus sulcafus, Otiorrhynchus ovai'us, Phaedon cochleariae,
Phyllobius pyri, Phyllotreta chrysocephala, Phyiiophaga sp,, Phyiiopertba hordeola,
Phyttotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona Uneatus and Sito-
philus granaria,
flies, mosquitoes. (Diptera), e.g. Aedes aegypti, Aedes albopictus, Aedes vexans, An-
astrepha tudens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus,
Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles mini-

177
mus, Anopheles quadrimacuiatus, Calliphora vicina, Ceratitis capitata, Chrysomya
bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis,
Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Contarinia sorghicola
Cordyiobia anthropophaga, Culicoides furens, Culex pipiens, Culex nigripaipus, Culex
quinquefasciatus, Culex tarsaiis, Cu/iseta inornata Culiseta melanura, Dacus cucurbi-
tae. Dacus oleae, Dasineura brassicae, Delia antique, Delia coarctata, Delia piatura,
Delia radicum, Dermatobia hominis, Fannia canicuiaris, Geomyza Tripunctaia, Gaster-
ophilus intestinal is, Glossina morsitans, Giossina pal pails, Glossina fuscipes, Giossina
tachinoides, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hylemyia
piatura, Hypoderma iineata, Leptoconops torrens, Liriomyza saiivae, Liriomyza trifolii,
Luciiia caprina, Lucilia cupr'ma, Lucilia sericata, Lycoria pectoralis, Mansonia titillanus,
Mayetioia destructor, Musca domestica, Muscina siabuians, Oestrus ovis, Opomyza
fforum, Oscineiia frit, Pegomya hysocyami, Phorbla aniiqua, Phorbia brassicae, Phor-
bia coarctata, Phlebotomus argentipes, Psorophora columbiae, Psila rosae, Psoro-
phora discolor, Prosimulium m/xturn, Rhagoletis cerasi, Rhagofetis pomonelia, Sar-
cophaga haemorrhoidalis, Sarcophaga sp., Simulium vittatum, Stomoxys calcitrans,
Tabanus bovinus, Tabanus atratus, Tabanus lineola, and Tabanus similis, T/'puia oi-
eracea, and Tipula paludosa
thrips {Thysanoptera), e.g. Dichromothrips corbetti, Dlchromothrips ssp , Franklinieila
fusca, Franklinieila occidentalis, Franklinieila tritici, Scirtothrips citri, Thrips oryzae,
Thrips palm/ and Thrips tabaci,
termites (Isoptera), e.g. Calofermes Havicollis, Leucofermes flavipes, Heterotermes
aureus, Reticuiitermes flavipes, Reticulitermes virginicus, Reticuiitermes lucifugus,
Termes natalensis, and Coptotermes formosanus,
cockroaches (Bfattaria - Blattodea), e.g. BSattetia germanica, Biattelia asahinae, Peri-
pfaneta americana, Periplaneta japonica, Peripfaneta brunnea, Peripianeta fufigginosa,
Periplaneta ausiralasiae, and Blatta orientalis,
true bugs (Hemiptera), e.g. Acrosternum hiiare, Blissus leucopterus, Cyrtopeltis nota-
tus, Dysdercus cingulatus, Dysdercus intermedins, Eurygasfer integriceps, Euschistus
impictiventris, Leptoglossus phyllopus, Lygus Hneolaris, Lygus pratensis, Nezara viridu-
ia, Piesma quadrata, Solubea insularis, Thyanta perditor, Acyrthosiphon onobrychis,
Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis forbesi, Aphis pom/, Aphis gos-
sypii, Aphis grossulariae, Aphis schneideri, Aphis spiraecola, Aphis sambuci, Acyrtho-
siphon pis urn, Aulacorthum so fan/', Bemisia argentifol/i, Brachycaudus cardui, Brachy-
caudus helichrysi, Brachycaudus persicae, Brachycaudus prunicola, Brevicoryne bras-
sicae, Capitophorus horni, Cerosipha gossypii, Chaetosiphon fragaefolii, Cryptornyzus
ribis, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicoia, Dysaulacorthum
pseudosolani, Dysaphis piantaginea, Dysaphis pyri, Empoasca fabae, Hyalopterus

178
pruni, Hyperomyzus lactucae, Macrosiphum avenae, Macrosiphum euphorbiae, Ma-
crosiphon rosae, Megoura viciae, Melanaphis pyrarius, Metopolophium dirhodum, My-
zus persicae, Myzus ascalonicus, Myzus cerasi, Myzus varians, Nasonovia ribis-nigri,
Nilaparvata lugens, Pemphigus bursar/us, Perkinsiella saccharic/da, Phorodon humuli,
Psylla rnali, Psyf/a pin] Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Rhopalosi-
phum pad/, Rhopalosiphum insertum, Sappaphis mala, Sappaphis mali, Schizaphis
graminum, Schizoneura lanuginosa, Sitobion avenae, Trialeurodes vaporariorum,
Toxoptera auranfHand, Viieus vitifolii, Cimsx lecfuiarius, Cimex hemipterus, Reduvius
senilis, Triatoma spp., and Aril us critatus.
ants, bees, wasps, sawflies (Hymenoptera), e.g. Athaiia rosae, Atta cephalotes, Atta
capiguara, Atta cephalotes, Atta laevigata, Atta robusta, Atta sexdens, Atta iexana,
Crematogaster spp., Hopiocampa minuta, Hoplocampa testudinea, Monomcrium pha-
raonis, Solenopsis geminata, Solenopsis invicta, Solenopsis richteri, Solenopsis xy/oni,
Pogonomyrmex barbatus, Pogonomyrmex caiifornicus, Pheidoie megacephala, Dasy-
mutilla occidentalis, Bombus spp. Vespula squamosa, Paravespula vulgaris, Paraves-
pula pennsylvanica, Paravespula germanica, Dolichovespula macula fa, Vespa crabro,
Po/lstes rubiginosa, Camponotus floridanus, and Linepithema humile,
crickets, grasshoppers, locusts (Orthoptera), e.g. Acheta domestica, Gryllotalpa gryllo-
talpa, Locusta migratoria, Melanoplus bivittatus, Meianoplus femurrubrum, Melanoplus
mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata,
Schistocerca americana, Schistocerca gregaria, Dociostaurus maroccanus, Tachycines
asynamorus, Oedaleus senegalensis, Zonozerus variegatus, Hieroglyphus daganensis,
Kraussaria angulifera, Calliptamus italicus, Chortoicetes terminifera, and Locustana
pardalina,
Arachnoidea, such as arachnids (Acarina), e.g. of the families Argasidae, ixodidae and
Sarcoptidae, such as Amblyomma americanum, Amblyomma variegatum, Ambryomma
maculatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus
microplus, Dermacentor silvarum, Dermacentor andersoni, Dermacentor variabilis,
Hyalomma truncafum, Ixodes ricinus, Ixodes rubicundus, Ixodes scapularis, Ixodes
holocyclus, Ixodes pacificus, Ornithodorus moubata, Omithodorus hermsi] Ornithodo-
rus turicata, Omithonyssus bacoti, Otobius megnini, Dermanyssus gallinae, Psoroptes
ovis, Rhipicephalus sanguineus, Rhipicephalus appendiculatus, Rhipicephalus everts/',
Sarcoptes scab/el, and Eriophyidae spp. such as Aculus schlechtendali, Phyllocoptrata
oleivoraand Eriophyes sheldon'r, Tarsonemfdae spp. such as Phytonemuspallidusand
Polyphagotarsonemus latus, Tenuipaipidae spp. such as Brevipa/pus phoenicis; Tetra-
nychidae spp. such as Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus
pacificus,' Tetranychus telarius and Tetranychus urticae, Panonychus ulmi, Panony-
chus citri, and Oligonychus pratensis; Araneida, e.g. Latrodectus mactans, and Loxos-
celes reclusa,

179
fleas (Siphonaptera), e.g. Ctenocephalides fells, Ctenocephalides cants, Xenopsylla
cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fasciatus,
silverfisn, firebrat (Thysanura), e.g. Lepisma saccharins and Thermobia domestica,
centipedes (Chilopoda), e.g. Scufigera cofeopfrata,
millipedes (Diplopoda), e.g. Narceusspp.,
Earwigs (Dermapterajt e.g. forficula auricuiaria,
iice (Phthiraptera), e.g. Pediculus humanus capitis, Pediculus humanus corporis, Pthi-
rus pubis, Haematopinus eurysternus, Haematopinus suis, Linognaihus vituti, Bovicola
bovis, Menopon gallinae, Menacanthus stramineus and Solenopotes capiilatus,
Plant parasitic nematodes such as root-knot nematodes, Meioidogyne arenaria, Melol-
dogyne chitwoodi, Meioidogyne exigua, Meioidogyne hapia, Meioidogyne incognita,
Meioidogyne javanlca and other Meioidogyne species; cyst nematodes, Globodera
rostochiensis, Globodera pallida, Globodera tabacum and other Globodera species,
Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, and
other Heterodera species; seed gall nematodes, Anguins funesta, Anguina triticimd
other Anguina species; stem and foliar nematodes, Aphelenchoides besseyi, Aphelen-
choides fragariae, Aphelenchoides ritzemabosi'and other Aphelenchoides species;
sting nematodes, Belonolalmus longlcaudatus and other Belonolaimus species; pine
nematodes, Bursaphelenchus xylophilus and other Bursaphelenchus species, ring ne-
matodes, Criconema species, Criconemella species, Criconemoides species, and Me-
socriconema species; stem and bulb nematodes, Ditylenchus destructor, Ditylenchus
dipsaci Ditylenchus mycellophagus and other Ditylenchus species,'awl nematodes,
Dolichodorus species; spiral nematodes, Helicotylenchus dihystera, Helicotylenchus
multlcinctus and other Helicotylenchus species, Rotylenchus robustus and other Roty-
lenchus species, sheath nematodes, Hemicycllophora species andHemlcriconembides
species; Hirshmannielta species; lance nematodes, Hoplolalmus columbus, Hoploial-
mus galeatus and other Hoplolalmus species, false root-knot nematodes, Nacobbus
aberrans and other Nacobbus species; needle nematodes, Longidorus elongates and
other Longidorus species; pin nematodes, Paratylenchus species; lesion nematodes,
Pratylenchus brachyurus, Pratylenchus coffeae, Pratytenchus curvitatus, Pratylenchus
goodeyi, Pratylencus neglectus, Pratylenchus penetrans, Pratylenchus scribneri, Praty-
lenchus vulnus, Pratylenchus zeae and other Pratylenchus species; Radinaphelen-
chus cocophilus and other Radinapheienchus species, burrowing nematodes, Rado-
pholus simllls and other Radopholus species; reniform nematodes, Rotylenchulus reni-
formls and other Rotylenchulus species; Scutellonem'a species; stubby root nemato-
des, Trichodorus primitlvus and other Trlchodorus species; Paratn'chodorus minor and

180
other Paratrichodorus species, stunt nematodes, Tylenchorhynchus claytoni, Tylen-
chorhynchus dub'sus and other Tylenchorhynchus species and Merlinius species; citrus
nematodes, Tyienchulus semipenefrans and other Ty/enchu/us species; dagger nema-
todes, Xiphinema americanum, Xiphinema index, Xiphinema diversicaudaturn and
other Xiphinema species, and other plant parasitic nematode species.
The formulations are prepared in a known manner (see e.g. tor review US 3,060,084,
EP-A 707 445 (for liquid concentrates), Browning, "Agglomeration", Chemical Engi-
neering, Dec. 4, 1967, 147-48, Perry's Chemical Engineer's Handbook, 4th Ed.,
McGraw-Hill, New York, 1963, pages 8-57 and et seq: WO 91/13546, US 4,172,714,
US 4,144,050, US 3,920,442, US 5,180,587, US 5,232,701, US 5,208,030,
GB 2,095,558, US 3,299,566, Klingman, Weed Control as a Science, John Wiley and
Sons, Inc., New York, 1961, Hance et a!., Weed Control Handbook, 8th Ed., Biackwe!!
Scientific Publications, Oxford, 1989 and Moliet, H., Grubemann, A., Formulation tech-
nology, Wiley VCH Verlag GmbH, Weinheim (Germany), 2001, 2. D. A, Knowies,
Chemistry and Technology of Agrochemical Formulations, Kluwer Academic Publish-
ers, Dordrecht, 1998 (ISBN 0-7514-0443-8), for example by extending the active com-
pound with auxiliaries suitable for the formulation of agrochemicals, such as solvents
and/or carriers, if desired emulsifiers, surfactants and dispersants, preservatives, anti-
foaming agents, anti-freezing agents, for seed treatment formulation also optionally
colorants and binders.
Examples of suitable solvents are water, aromatic solvents (for example Solvesso
products, xylene), paraffins (for example mineral oil fractions), alcohols (for example
methanol, butanol, pentanol, benzyl alcohol), ketones (for example cyclohexanone,
gamma-butyrolactone), pyrrolidones "(NMP, NOP), acetates (glycol diacetate), glycols,
fatty acid dirnethylarnides, fatty acids and fatty acid esters. In principle, solvent mix-
tures may also be used.
Examples of suitable carriers are ground natural minerals (for example kaolins, clays,
talc, chalk) and ground synthetic minerals (for example highly disperse silica, silicates).
Suitable emulsifiers are nonionic and anionic emulsifiers (for example polyoxyethyiene
fatty alcohol ethers, alkylsulfonates and arylsuSfonates).
Examples of dispersants are lignin-sulfite waste liquors and methylcelluiose.
Suitable surfactants used are alkali metal, alkaline earth metal and ammonium salts of
lignosulfonic acid, naphthaienesuifonic acid, phenolsulfonfc-acid, dibutylnaphthalene-
sulfonic acid, alkylarylsuffonat.es, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates,
fatty acids and sulfated fatty alcohol glycol ethers, furthermore condensates of sul-
fonated naphthalene and naphthalene derivatives with formaldehyde, condensates of

181
naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, poly-
oxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol,
alkylphenol poiyglycol ethers, tributylphenyl polyglycol ether, tristearyiphenyl polyglycol
ether, alkylaryl polyether alcohols, alcohol and fatty alcohol ethylene oxide conden-
sates, ethoxylated castor oil, polyoxyethyfene alkyl ethers, ethoxyiated polyoxypropyl-
ene, lauryi alcohol pofyglyco! ether aceta!, sorbitol esters, lignosulfite waste liquors and
methyjcelfulose.
Substances which are suitable for the preparation of directly sprayable solutions, emul-
sions, pastes or oil dispersions are mineral oil fractions of medium to high boiling point,
such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal
origin, aliphatic, cyclic and aromatic hydrocarbons, for example toluene, xylene, paraf-
fin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, etha-
noi; propanol, butanol, cyclohexanol, cyciohexanone, isophorone, highly polar solvents,
for example dimethyl sulfoxide, N-methylpyrrolidone or water.
Also anti-freezing agents such as glycerin, ethylene glycol, propylene glycol and bacte-
ricides such as can be added to the formulation.
Suitable antifoaming agents are for example antifoaming agents based on silicon or
magnesium stearate.
Powders, materials for spreading and dustable products can be prepared by mixing or
concomitantly grinding the active substances with a solid carrier.
Granules, for example coated granules, impregnated granules and homogeneous
granules, can be prepared by binding the active compounds to solid carriers. Examples
of solid carriers are mineral earths such as silica gels, silicates, taic, kaolin, attaclay,
limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate,
magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as,
for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and
products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nut-
shell meal, cellulose powders and other solid carriers.
In general, the formulations comprise from 0.01 to 95% by weight, preferably from 0.1
to 90% by weight, of the active compound(s). In this case, the active compound(s) are
employed in a purity of from 90% to 100% by weight, preferably 95% to 100% by
weight (according to NMR spectrum).
The compounds of formula I can be used as such, in the form of their formulations or
the use forms prepared therefrom, for example in the form of directly sprayable solu-
tions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusta-

182
bfe products, materials for spreading, or granules, by means of spraying, atomizing,
dusting, spreading or pouring. The use forms depend entirely on the intended pur-
poses; they are intended to ensure in each case the finest possible distribution of the
active compound(s) according to the invention.
Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable
powders (sprayable powders, oil'dispersions) by adding water. To prepare emulsions,
pastes or oil dispersions, the substances, as such or dissolved in an oil or solvent, can
be homogenized in water by means of a wetter, tackifier, dispersant or emulsifier.
However, it is also possible to prepare concentrates composed of active substance,
wetter, tackifier, dispersant or emuisifier and, if appropriate, solvent or oil, and such
concentrates are suitable for dilution with water.
The active compound concentrations in the ready-to-use preparations can be varied
within relatively wide ranges. In general, they are from 0.0001 to 10%, preferably from
0.01 to 1% per weight.
The active compound(s) may also be used successfully in the ultra-low-volume process
(ULV), It being possible to apply formulations comprising over 95% by weight of active
compound, or even to apply the active compound without additives.
The following are examples of formulations: 1. Products for dilution with water for foliar
applications. For seed treatment purposes, such products may be applied to the seed
diluted or undiluted.
A) Water-soluble concentrates (SL, LS)
10 parts by weight of the active compound(s) are dissolved in 90 parts by weight of
water or a water-soluble solvent. As an alternative, wetters or other auxiliaries are
added. The active compound(s) dissolves upon dilution with water, whereby a formula-
tion with 10 % (w/w) of active compound(s) is obtained.
B) Dispersible concentrates (DC)
20 parts by weight of the active compound(s) are dissolved in 75 parts by weight of
cyciohexanone with addition of 10 parts by weight of a dispersant, for example polyvi-
nylpyrrolidone. Dilution with water gives a dispersion, whereby a formulation with 20%
(w/w) of active compound(s) is obtained.
C) Emulsifiable concentrates (EC)
15 parts by weight of the active compound(s) are dissolved in 75 parts by weight of
xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in

183
each case 5 parts by weight). Dilution with water gives an emulsion, whereby a formu-
lation with 15% (w/w) of active compoundfs) is obtained.
D)- Emulsions (EW, EO, ES)
40 parts by weight of the active compound(s) are dissolved in 35 parts by weight of
xylene with addition of calcium dodecyibenzenesulfonate and castor oil ethoxylate (in
each case 5 parts by weight). This mixture is introduced into 30 parts by weight of wa-
ter by means of an emulsifier machine (e.g. Ultraturrax) and made into a homogeneous
emulsion. Dilution with water gives an emulsion, whereby a formulation with 25% (w/w)
of active compoundfs is obtained.
E) Suspensions (SC, OD, FS)
In an agitated ball mill, SfJparts by weight of the active compound(sy are comminuted
with addition of 10 parts by weight of dispersants, wetters and 70 parts by weight of
water or of an organic solvent to give a fine active compound(s) suspension. Dilution
with water gives a stable suspension of the active compound(s), whereby a formulation
with 20% (w/w) of active compound(s) is obtained.
F) Water-dispersible granules and water-soluble granules (WG, SG)
50 parts by weight of the active compound(s) are ground finely with addition of 50 parts
by weight of dispersants and wetters and made as water-dispersible or water-soluble
granules by means of technical appliances (for example extrusion, spray tower, fluid-
ized bed). Dilution with water gives a stable dispersion or solution of the active com-
poundfs), whereby a formulation with 50% (w/w) of active compound(s) is obtained.
G) Water-dispersible powders and water-soluble powders (WP, SP, SS, WS)
75 parts by weight of the active compoundfs) are ground in a rotor-stator mill with addi-
tion of 25 parts by weight of dispersants, wetters and silica gel. Dilution with water
gives a stable dispersion or solution of the active compound(s), whereby a formulation
with 75% (w/w) of active compound(s) is obtained.
2. Products to be applied undiluted for foliar applications. For seed treatment pur-
poses, such products may be applied to the seed diluted or undiluted.
H) Dustable powders (DP, DS)
5 parts by weight of the active compound(s) are ground finely and mixed intimately with
95 parts by weight of finely divided kaolin. This gives a dustable product having 5%
(w/w) of active compound(s)

184
I) Granules (GR, FG, GG, MG)
0.5 part by weight of the active compound(s) is ground finely and associated with 95.5
parts by weightof carriers, whereby a formulation with 0,5% (w/w) of active com-
pound) is obtained. Current methods are extrusion, spray-drying or the fiuidized bed.
This gives granules to be applied undiluted for foliar use.
J) ULV solutions (UL, LS)
10 parts by weight of the active compound(s) are dissolved in 90 parts by weight of an
organic solvent, for example xylene. This gives a product having 10% (w/w) of active
compound(s), which is applied undiluted for foliar use.
Various types of oils, wetters, adjuvants, herbicides, fungicides, other pesticides, or
bactericides may be added to the active ingredients, if appropriate just immediately
prior to use (tank mix). These agents usually are admixed with the agents according to
the invention in a weight ratio of 1:10 to 10:1.
The compounds of formula I are effective through both contact and ingestion.
The compounds of formula i are also suitable for the protection of the seed, plant
propagules and the seedlings' roots and shoots, preferably the seeds, against soil
pests and also for the treatment plant seeds which tolerate the action of herbicides or
fungicides or insecticides owing to breeding, including genetic engineering methods.
Conventional seed treatment formulations include for example flowable concentrates
FS,. solutions LS, powders for dry treatment DS, water dispersible powders WS or
granules for slurry treatment, water soluble powders SS and emulsion ES. Application
to the seeds is carried out before sowing, either directly on the seeds.
The seed treatment application of the compounds of formula I or formulations
containing them is carried out by spraying or dusting the seeds before sowing of the
plants and before emergence of the plants.
The invention also relates to the propagation product of plants, and especially the
treated seed comprising, that is, coated with and/or containing, a compound of formula
i or a composition comprising it. The term "coated with and/or containing" generally
signifies that the active ingredient is for the most part on the surface of the propagation
product at the time of application, although a greater or lesser part of the ingredient
may penetrate into the propagation product, depending on the method of application.
When the said propagation product is (re)planted, it may absorb the active ingredient.

185
The seed comprises the inventive compounds or compositions comprising them.in an
amount of from 0,1 g to 10 kg per 100 kg of seed.
Compositions of this invention may also contain other active ingredients, for example
other pesticides, insecticides, herbicides, fertilizers such as ammonium nitrate, urea,
potash, and superphosphate, phytotoxicants and plant growth regulators, safeners and
nematodes. These additional ingredients may be used sequentially or in combination
with the above-described compositions, if appropriate also added only immediately
prior to use (tank mix). For example, the p!ant{s) may be sprayed with a composition of
this invention either before or after being treated with other active ingredients.
The following list of pesticides together with which the compounds according to the
invention can.be used, is intended to illustrate the possible combinations, but not to
impose any limitation:
A.1, Organo(fhio)phosphates: acephate, azamethiphos, azinphos-methyl, chlorpyrifos,
chlorpyrifos-methyl, chlorfenvinphos, diazinon, dichlorvos, dicrotophos, dimethoate,
disulfoton, ethion, fenitrothion, fenthion, isoxathion, malathion, methamidophos, methi-
dathion, methyl-parathion, mevinphos, monocrotophos, oxydemeton-methyl, paraoxon,
parathion, phenthoate, phosalone, phosmet, phosphamidon, phorate, phoxim, pirimi-
phos-methyl, profenofos, prothiofos, sulprophos, tetrachlorvinphos, terbufos, triazo-
phos, trichiorfon;
A.2. Carbamates: alanycarb, aldicarb, bendiocarb, benfuracarb, carbaryl, carbofuran,
carbosulfan, fenoxycarb, furathiocarb, methiocarb, methomyl, oxamyl, pirimicarb, pro-
poxur, thiodicarb, triazamate;
A.3. Pyrethroids: allethrin, bifenthrin, cyfluthrin, cyhalothrin, cyphenothrin, cyperme-
thrin, aipha-cypermethrin, beta-cypermefhrin, zeta-cypermethrin, deltamethrin, esfen-
valerate, etofenprox, fenpropafhrin, fenvalerate, imtprothrin, lambda-cyhalothrin, per-
methrin, praliethrin, pyrethrin I and II, resmethrin, silafluofen, tau-fluvalinate, tefluthrin,
tetramethrin, traiomethrin, transfluthrin;
A.4. Growth regulators: a) chitin synthesis inhibitors: benzoylureas: chlorfiuazuron,
cyramazin, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, iufenuron, no-
valuron, tefl.ubenzuron, triflumuron; buprofezin, diofenolan, hexythiazox, etoxazole,
ciofentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide,
azadirachtin; c) juvenoids: pyriproxyfen, methoprene, fenoxycarb; d) lipid biosynthesis
inhibitors: spirodiclofen, spiromesifen, a tetronic acid derivative of formula r1,

186

A.5. Nicotinic receptor agonists/antagonists compounds: clothianidin, dinotefuran, imi-
dacloprid, thiamethoxam, nitenpyram, acetamiprid, thiacioprid;
A.6. GABA antagonist compounds: acetoproie, endosuifan, ethiprole, fipronii, va-
niliproSe;
A.7. Macrocyclic lactone insecticides: abamectin, emamectin, milbemectin, lepimectin,
spinosad*
A.S. MET! I acaricides: fenazaquin, pyridaben, tebufenpyrad, tolfenpyrad;
A.9. MET! il and III compounds: acequinocyl, fluacyprim, hydramethylnon;
A.10. Uncoupler compounds: chiorfenapyr;
A.11. Oxidative phosphorylation inhibitor compounds: cyhexatin, diafenthiuron, fenbu-
tatin oxide, propargite;
A.12. Moulting disruptor compounds: cryomazine;
A.13. Mixed Function Oxidase inhibitor compounds: piperonyi butoxide;
A. 14, Sodium channel blocker compounds: indoxacarb, metafiumizone;
A. 15. Various: benclothiaz, bifenazate, cartap, fionicamid, pyridalyl, pymetrozine, sul-
fur, thiocyclam, N-R'-2,2-dihalo-1-R"cyclo-propanecarboxamide-2-(2,5-dichioro-a,a,a-
trifluoro-p-toiy!)hydrazone or N-R'-2,2-di(R'")propionamide-2-(2,6-d!chioro-a,a,a-
trifluoro-p-toiy[)-hydrazone, wherein R' is methyl or ethyl, halo is chloro or bromo, R" is
hydrogen or methyl and R'" is methyi or ethyl, and the aminoisothiazole compounds of
formula T2,

wherein Rj is -CH2OCH2CH3 or H and R" is CF2CF2CF3 or CH2CH{CH3)3,
anthraniiamide compounds of formula r3

187

wherein B1 fs hydrogen or a chlorine atom, B2 is a bromine atom or CF3, and RB is CH3
or CH(CH3)2, and malononitrile compounds as described in JP 2002 284608,
WO 02/89579, WO 02/90320, WO 02/90321, WO 04/06677, WO 04/20399, or JP 2004
99597.
The insects may be controlled by contacting the target parasite/pest, its food supply,
habitat, breeding ground or its locus with a pesticidally effective amount of compounds
of or compositions of formula i.
"Locus" means a habitat, breeding ground, plant, seed, soil, area, material or environ-
ment in which a pest or parasite is growing or may grow.
In general, "pesticidally effective amount" means the amount of active ingredient
needed to achieve an observable effect on growth, including the effects of necrosis,
death, retardation, prevention, and removal, destruction, or otherwise diminishing the
occurrence and activity of the target organism. The pesticidally effective amount can
vary for the various compounds/compositions used in the invention. A pesticidally ef-
fective amount of the compositions will also vary according to the prevailing conditions
such as desired pesticidal effect and duration, weather, target species, locus, mode of
application, and the like.
The compounds or compositions of the invention can also be applied preventively to
places at which occurrence of the pests is expected.
The compounds of formula I may also be used to protect growing plants from attack or
infestation by pests by contacting the plant with a pesticidally effective amount of com-
pounds of formula I. As such, "contacting" includes both direct contact (applying the
compounds/compositions directly on the pest and/or plant - typically to the foliage,
stem or roots of the plant) and indirect contact (applying the compounds/compositions
to the locus of the pest and/or plant).
In the case of soil treatment or of application to the pests dwelling place or nest, the
quantity of active ingredient ranges from 0.0001 to 500 g per 100 m2, preferably from
0.001 to 20 g per 100 m2.

188
For use in treating-crop plants, the rate of application of the active ingredients of this
invention may be in the range of 0.1 g to 4000 g per hectare, desirably from 25 g to
600 g per hectare, more desirably from 50 g to 500 g per hectare.
Compounds of formula i and compositions comprising them can also be used for con-
trolling and preventing infestations and infections in animals including warm-blooded
animals (including humans) and fish. They are for example suitable for controlling and
preventing infestations and infections in mammals such as cattle, sheep, swine, cam-
els, deer, horses, pigs, poultry, rabbits, goats, dogs and cats, water buffalo, donkeys,
fallow deer and reindeer, and also in fur-bearing animals such as mink, chinchilla and
raccoon, birds such as hens, geese, turkeys and ducks and fish such as fresh- and
salt-water fish such as trout, carp and eels.
Infestations in warm-blooded animals and fish include, but are not limited to, lice, biting
lice, ticks, nasal bois, keds, biting flies, muscoid flies, flies, myiasitic fly larvae, chig-
gers, gnats, mosquitoes and fleas.
The compounds of formula ! and compositions comprising them are suitable for sys-
temic and/or non-systemic control of ecto- and/or endoparasites. They are active
against all or some stages of development.
Administration can be carried out both prophylacticaily and therapeutically.
Administration of the active compounds is carried out directly or in the form of suitable
preparations, orally, topically/dermaily or parenterally.
For oral administration to warm-blooded animals, the formula I compounds may be
formulated as animal feeds, animal feed premixes, animal feed concentrates, pills, so-
lutions, pastes, suspensions, drenches, gels, tablets, boluses and capsules. In addi-
tion, the formula I compounds may be administered to the animals in their drinking wa-
ter. For oral administration, the dosage form chosen should provide the animal with
0.01 mg/kg to 100 mg/kg of animal body weight per day of the formula I compound,
preferably with 0.5 mg/kg to 100 mg/kg of animal body weight per day.
Alternatively, the formula I compounds may be administered to animals parenterally, for
example, by intraruminal, intramuscular, intravenous or subcutaneous injection. The
formula I compounds may be dispersed or dissolved in a physiologically acceptable
carrier for subcutaneous injection. Alternatively, the formula I compounds may be for-
mulated into an implant for subcutaneous administration. In addition the formula i com-
pound may be transdermal administered to animals. For parenteral administration,
the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of
animal body weight per day of the formula I compound.

189
The formula I compounds may also be applied topically to the animals in the form of
dips, dusts, powders, collars, medallions, sprays, shampoos, spot-on and pour-on for-
mulations and in ointments or oil-i'n-water or water-in-oil emulsions. For topical applica-
tion, dips and sprays usually contain 0.5 ppm to 5,000 ppm and preferably 1 ppm to
3,000 ppm of the formula [ compound, in addition, the formula I compounds may be
formulated as ear tags for animals, particularly quadrupeds such as cattle and sheep.
Suitable preparations are:
- Solutions such as oral solutions, concentrates for oral administration after dilution,
solutions for use on the skin or in body cavities, pouring-on formulations, gels;
- Emulsions and suspensions for oral or derma! administration; semi-solid prepara-
tions;
- Formulations in which the active compound is processed in an ointment base or in
an oil-in-water or wafer-in-oil emulsion base;
- Solid preparations such as powders, premixes or concentrates, granules, pellets,
-tablets, boluses, capsules; aerosols and inhalants, and active compound-containing
shaped articles.
Generally it is favorable to apply solid formulations which release compounds of for-
mula I in total amounts of 10 mg/kg to 300 mg/kg, preferably 20 mg/kg to 200 mg/kg.
The active compounds can also be used as a mixture with synergists or with other ac-
tive compounds which act against pathogenic endo- and ectoparasites.
In general, the compounds of formula ! are applied in parasiticidally effective amount-
meaning the amount of active ingredient needed to achieve an observable effect on
growth, including the effects of necrosis, death, retardation, prevention, and removal,
destruction, or otherwise diminishing the occurrence and activity of the target organism.
The parasiticidally effective amount can vary for the various compounds/compositions
used in the invention. A parasiticidally effective amount of the compositions will also
vary according to the prevailing conditions such as desired parasiticfdal effect and du-
ration, target species, mode of application, and the like.
Synthesis Examples
With due modification of the starting compounds, the protocols shown in the synthesis
examples below were used for obtaining further compounds I. The resulting
compounds, together with physical data, are listed in the Tables 1 to 3 which follow.
2-[5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazol-3-yl]-8-methyi-benzo[d] [1,3]oxazin-4-
one is known from WO 04/011447.

190
Example 1
Methyl-(3henyl-suJfamoyl-N-(5-bromo-2-(3-chloro-pyriciin-2-yl)-2H-pyrazole-3-carboxylic
acid (2-carbamoy[-6-mefhyl-pheny[))-amide, compound 1.1-33.-
G.089 g Methyl-phenyl-sulfamoyl-amine was dissolved in 5 m! methylene chloride.
0.017 g-sodium hydride was added at 20-25°C and the solution was stirred for 1hour.
0.20 g2-[5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazol-3-yl]-8-methy!-benzo[d]
[1,3joxazin-4-one were added and the resulting mixture was refluxed for 24h. The sol-
vent was removed and the residue was purified by column chromatography (cyclo hex-
ane/ ethyl acetate 1:2) to yield 0.18 g methyi-phenyi-suifamoyl-N-(5-bromo-2-(3-chloro-
pyr!din-2-y!)-2H-pyrazo[e-3-carboxyIlc acid {2-carbamoy!-6-methyl-phenyS))-3rnide
Example 2
Step A: Preparation of 5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazoSe-3-carboxylic acid
(2-carbamoyl-6-methy!-phenyl)-amide
1.00 g 2-[5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazo!-3-yi]-8-methyl-benzo[d]
[1,3]oxazin-4-one was taken up in 10 ml of a 25% ammonia solution in water and
stirred for 72 h. The solids were filtered and washed with co!d water to yield 0.80 g of
the amide.
StepB: S,S-Dimethyl-N-(5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxyiic
acid (2-carbamoyl-6-methyl-pheny!))-suifimide, compound 1.3-2.
0.071 mi DMSO were dissolved under a nitrogen atmosphere in 0.5 ml methylene chlo-
ride and cooled to -60 °C. 0.14 ml trifiuoroacetic acid anhydride were siowly added at
this temperature followed by the addition of 0.20g 5-bromo-2~(3-chloro~pyridin-2-yl)-2H-
pyrazole-3-carboxylic acid (2-carbarnoyl-6-rnethyl-phenyl)-amide. The resulting solution
was stirred at -35°C for 1h. After diluting with 5 ml methylene chloride, the reaction
mixture was extracted with aqueous sodium hydroxide once and two times with water.
The organic solvent was dried and the solvent removed. The residue was diluted with
diethyl ether and the solid residue was filtered off and dried to yield 0.08 g of the de-
sired sulfimide.

191
Example 3
S,S Dimethyl - S- AminosuSfonium mesitylenesulfonate was prepared according to Y.
Tam'ura et ai, Tetrahedron, 1975, 31, 3035-3040.
S,S-Dimethy!-N-(5-bromo--2-(3-chloro-pyriclin-2-y!)-2H-pyrazoi9-3-carboxyiicacicl (2-
carbamoyi-6-methy!-phenyl))-suifimideJ compound 1.3-2.
0.2 g S,S Dimethyl - S- Aminosuifonium mesitylenesulfonate were dissolved in 20 ml
methylene chioride. 0.26 g potassium t-butytate, 0.54 g 2-[5-Bromo-2-(3-chloro-pyridin-
2-yI)-2H-pyrazo!-3-yn-8-methyl-benzo[d] [1,3]oxazin-4-one were added and the result-
ing mixture was stirred at 20-25°C for additional 3.5 h. The reaction mixture was ex-
tracted with aqueous sodium hydroxide once and two times with water. The organic
solvent was dried andthe solvent removed. Column chromatography yielded -0.3 g of
the desired product.
Example 4
2-{2-[5-Bromo-2-(2-chIoro-phenyl)-2H-pyrazoi-3-yl]-2-oxo-ethyi}-5»chloro-3-methyi-N-
(1 -oxo-hexahydro-1 iambda*6*-thiopyran-1 -y!idene)-benzamide
0.2g2-{2-[5-Bromo-2-(2-chloro-phenyl)-2H-pyrazol-3-yl]-2-oxo-ethyl}-5-chlorO'3-
methy[-N-{tetrahydro-1[ambda*4*-thiopyran-1-ylidene)-benzamide (0.35 mmol) were
dissolved in 10 ml acetic acid. 4 mg Sodium woiframate dihydrate were added. 45 mg
of a 30 % solution of hydrogenperoxide was added dropwise and the resulting solution
was stirred for 18 h. The reaction mixture was poured into a saturated aqueous sodium
carbonate solution, methylene chloride was added and the organic pase was subse-
quently washed with water and saturated aqueous sodium carbonate. The organic sol-
vent was dried and the solvent removed. Column chromatography yielded 0.07 g of the
desired product, compound I.4-22.
The products were characterized by coupled High Performance Liquid
Chromatography / mass spectrometry (HPLC/MS), by NMR or by their melting points.

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Examples for the action against harmful pests
1.. Activity against Boll weevil {Anthonomus grandis)
The active compounds were formulated in 1:3 DMSO : water. 10 to 15 eggs were
placed into microtiterplates filled with 2% agar-agar in water and 300 ppm formaline;
The eggs were sprayed with 20 pi of the test solution, the plates were sealed with
pierced foils and kept at 24-26°C and 75-85% humidity with a day/night cycle for 3 to 5 days. Mortality was assessed on the basis of the remaining unhatched eggs or larvae
on the agar surface and/or quantity and depth of the digging channels caused by the
hatched larvae. Tests were replicated 2 times.
in this test, compounds 1.1-3, 1.1-11,1.1-15,1.1-32, 1.1-35, 1.1-48,1.1-69,1.2-2, 1=3-1,
1.3-3, 1.3-4, 1.3-5, 1.3-6, 1.3-7, 1.3-8,1.3-9, 1.3-10, 1.3-11, 1.3-12, 1.3-13, 1-3-14, 1.3-19, 1.3-
20, 1.3-21, I.3-22, 1.3-23, (.3-24, I.3-25, 1.3-26, I.3-27, i.3-28, i.3-29, I.3-30,1.3-31, I.3-
32, i.3-33, 1.3-34, I.3-35,1.3-36, I.3-37, I.3-38, I.3-39, 1.3-40, 1.3-41, 1.3-42,1.3-43, I.3-
44, 1.3-45, 1.3-46, 1.3-47,1.3-48, 1.3-49, 1.3-51, 1.3-52, 1.3-53,1.3-54, I.3-55,1.3-56, I.3-
57, I.3-58, 1.4-1, I.4-2,1.4-3, 1.4-4, I.4-5, I.4-6, L4-7, I.4-8,1.4-9, 1.4-10, 1.4-11, 1.4-12, I.4-
13, 1.4-14,1.4-15,1.4-16,1.4-17, [.4-22, and I.4-23 at 2500 ppm showed over 75 % mor-
tality.
2. Activity against Mediterranean fruitfly {Ceratitis capitata)
The active compounds were formulated in 1:3 DMSO: water. 50 to 80 eggs were
placed into microtiterplates filled with 0.5% agar-agar and 14 % diet in water. The eggs
were sprayed with 5 u! of the test solution, the plates were sealed with pierced foils and
kept at 27-29°C and 75-85% humidity under fluorescent light for 6 days. Mortality was
assessed on the basis of the agility of the hatched larvae. Tests were replicated 2
times.
In this test, compounds 1.1-12, 1.1-38,1.1-43, 1.1-44, 1.1-49, 1.3-1,1.3-8,1.3-9, 1.3-10,
1.3-11, 1.3-12, 1.3-13, 1.3-14, 1.3-19, I.3-20, 1.3-22, I.3-23, i.3-24, i.3-25, I.3-26, I.3-27,
I.3-28, I.3-29, 1.3-30, I.3-32, I.3-33, 1.3-34, I.3-35,1.3-37, I.3-38,1.3-39, f.3-40, 1.3-41,
1.3-42, I.3-43, I.3-44, f.3-45, I.3-46, I.3-47, I.3-48,1.3-49, 1.3-51, 1.3-52, I.3-53, I.3-54,
I.3-55, i.3-56, I.3-57, I.3-58, 1.4-1, 1.4-2,1.4-3, 1.4-4, 1.4-5,1.4-6, 1.4-7, 1.4-8, 1.4-9, 1.4-10,
1.4-11, 1.4-12, 1.4-13,1.4-15, 1.4-16, 1.4-17, 1.4-22 and i.4-23 at 2500 ppm showed over
75 % mortality.
3. Activity against Tobacco budworm {Heliothis virescens)
The active compounds were formulated in 1:3 DMSO : water. 1.5 to 25 eggs were
placed into microtiterplates filled with diet. The eggs were sprayed with 10 pi of the test

209
solution, the plates were sealed with pierced foils and kept at 27-29°C and 75-85%
humidity under fluorescent light for 6 days. Mortality was assessed on the basis of the
agility and of comparative feeding of the hatched larvae. Tests were replicated 2 times.
4. In this test, compounds i.1-1,1.1-3, 1.1-10, 1.1-11, 1.1-12, 1/1-13, 1.1-14, 1.1-15, 1.1-
16, 1.1-19, 1.1-21, 1.1-24, 1.1-28, 1.1-31, 1.1-32, 1.1-34, 1.1-35, 1.1-36, 1.1-38, 1.1-
39, 1.1-40, 1.1-41, 1.1-42, 1.1-43, i.1-44, 1.1-46, 1.1-48, 1.1-49, 1.1-53, 1.1-54, 1.1-
62, 1.1-66, 1.1-67, 1.1-69, 1.2-1, 1.2-2, 1.2-3, 1.2-4, 1.2-5, 1.2-6, 1.3-1, I.3-3, I.3-4,
1.3-5, I.3-6, (.3-7, L3-8, I.3-9, 1.3-10, 1.3-11, 1.3-12, 1.3-13, 1.3-14, 1.3-19, I.3-20,
1.3-21, 1.3-22, I.3-23, 1.3-24, I.3-25, I.3-26, I.3-27, 1.3-28, 1.3-29, i.3-30, 1.3-31,
1.3-32, 1.3-33, I.3-34, 1.3-35, I.3-36, I.3-37, I.3-38, I.3-39,1.3-40, 1.3-41, I.3-42,
I r\ J *-, 1 rt jt A I r\ J r- i n A r\ \ '5 ! -\A
I.J-J, LvS-f, l.-J-O, I.O-fD, I.O-t/, i.O'HO, t,0"+Z>, l.O-J!, !,lJ->Ji, HJ"- 1,3-55, 1.3-56, 1.3-57 , 1.3-53, 1.4-1, 1.4-2, 1.4-3, 1.4-4, 1.4-5,1.4-6, 1.4-7, 1.4-8, 1.4-
9, 1.4-10, 1.4-11, 1.4-12, 1.4-13, 1.4-14, 1.4-15, 1.4-16, 1.4-17, I.4-22 and 1.4-23 at
2500 ppm showed over 75 % mortality.
4. Activity against Vetch aphid (Megoura viciae)
The active compounds were formulated in 1:3 DMSO: water. Bean leaf disks were
placed into microtiterplates filled with 0.8% agar-agar and 2.5 ppm OPUS™. The leaf
disks were sprayed with 2.5 pi of the test solution and 5 to 8 adult aphids were placed
into the microtiterplates which were then closed and kept at 22-24°C and 35-45% un-
der fluorescent light for 6 days. Mortality was assessed on the basis of vital, repro-
duced aphids. Tests were replicated 2 times.
In this test, compounds 1.1-12, 1.1-19, 1.1-32,1.1-49,1.1-50, 1.1-53, I.2-9, 1.3-1, I.3-3,
I.3-4, I.3-5, I.3-6, I.3-7, I.3-8, I.3-9,1.3-10, 1.3-11, 1.3-12,1.3-13, 1.3-14,1.3-19, 1.3-20,
1.3-21, I.3-22, i.3-23, L3-24, I.3-25,1.3-26, 1.3-27,1.3-28, 1.3-29, I.3-30, I.3-32, 1.3-33,
I.3-34, I.3-35, 1.3-36, I.3-37, 1.3-38,1.3-39, 1.3-40,1.3-41, 1.3-42, I.3-43, I.3-44, 1.3-45,
t.3-47, I.3-49, 1.3-51, i.3-52, i.3-53, I.3-54, I.3-55,1.3-56, I.3-57, 1.3-58, 1.4-1,1.4-2; I.4-3,
I.4-4, I.4-5, I.4-6, I.4-7, 1.4-8, I.4-9,1.4-10,1.4-11, 1.4-12, 1.4-13,1.4-14,1.4-15, 1.4-16,
1.4-17,1.4-22 and t.4-23 at 2500 ppm showed over 75 % mortality compared to 0%
mortality of untreated controls.
5. Activity against Oat aphid {Rhopalosiphum pad!)
The active compounds were formulated in 1:3 DMSO : water. Barlay leaf disk were
placed into microtiterplates filled with 0.8% agar-agar and 2.5 pprn OPUS™ .The leaf
disks were sprayed with 2.5 pi of the test solution and 3 to 8 adult aphids were placed
into the microtiterplates which were then closed and kept at 22-24°C and 35-45% hu-
midity under fluorescent light for 5 days. Mortality was assessed on the basis of vital
aphids. Tests were replicated 2 times.

210
in this test, compound 1,3-1 at 2500 ppm showed over 75 % mortality compared io 0%
mortality of untreated controls.
6. Activity against Cotton aphid (Aphis gossypii)
The active compounds were formulated in 50:50 acetone:water and 100 ppm Kinetic™
surfactant
Cotton plants at the cotyledon stage (one plant per pot) were infested by placing a
heavily infested leaf from the main colony on top of each cotyledon. The aphids were
allowed to transfer to the host plant overnight, and the leaf used to transfer the aphids
was removed. The cotyledons were dipped in the test solution and allowed to dry. After
5 days, mortality counts were made.
In this test, compound 1.3-1,1.3-3, i.3-4,1.3-5,1.3-6,1.3-7,1.3-8,1.3-9, 1.3-10,1.3-11,I.3-
12, 1.3-13,1.3-14,-1.3-15,1.3-16, 1.3-17, 1.3-18,1.3-19, 1.3-20, 1.3-21,1.3-22, 1.3-23, 1.3-
24, 1.3-25,1.3-26, 1.3-27,1.3-28, 1.3-29, 1.3-30,1.3-32, 1.3-33, 1.3-34,1.3-35,1.3-36, 1.3-
38, 1.3-39,1.3-40, 1.3-41,1.3-42, 1.3-43,1.3-44, 1.3-51, [.3-52, I.3-53,1.3-54,1.4-1, 1.4-2,
I.4-3, I.4-4, 1.4-5, I.4-6, I.4-7, i.4-8,1.4-9, 1.4-10,1.4-11, 1.4-12, 1.4-13 and 1.4-16 at 300
ppm showed over 50% mortaiity.
7. Activity against Southern armyworm [Spodoptera eridania), 2nd instar larvae
The active compounds were formulated for testing the activity against insects and
arachnids as a 10.000 ppm solution in a mixture of 35% acetone and water, which was
diluted with water, if needed,
A Sieva iima bean leaf was dipped in the test solution and allowed to dry. The leaf was
then placed in a petri dish containing a filter paper on the bottom and ten 2nd instar
caterpillars. At 5 days, observations are made of mortality and reduced feeding.
In this test, compounds 1.1-1,1.1-3,1.1-7,1.1-9,1.1-10,1.1-11,1.1-12, 1.1-13,!.1-14,
1.1-15, 1.1-16, 1.1-19, 1.1-21, 1.1-24,1.1-27, 1.1-28, 1.1-30, 1.1-31, 1.1-32, 1.1-34,1.1-35,
1.1-36, f.1-38, 1.1-39, 1.1-40, 1.1-41,1.1-42, 1.1-43,1.1-44, (.1-45, 1.1-46, 1.1-47,1.1-49,
1.1-53, f.1-54, 1.1-57, 1.1-61, 1.1-63, 1.1-66, 1.1-69,1.2-1, S.2-2, 1.2-3, I.2-4, 1.2-5, J.2-6,
i.2-8, 1.2-9, I.3-3, L3-4, I.3-5, I.3-6, I.3-7, I.3-8, I.3-9, 1.3-10, 1.3-11, 1.3-12, 1.3-13, 1.3-14,
1.3-15, 1.3-16, 1.3-17, 1.3-18, 1.3-19, I.3-20, 1.3-21, I.3-22, I.3-23, I.3-24, I.3-25, I.3-26,
1.3-27, I.3-28, I.3-29, I.3-30, f.3-32,1.3-33, i.3-34, I.3-35, I.3-37, I.3-38, I.3-39,1.3-40,
1.3-41, 1.3-42, 1.3-43, I.3-44, 1.3-51,1.3-52, i.3-53, I.3-54, 1,4-1, I.4-2, I.4-3, f.4-4, I.4-5,
I.4-6, J.4-7, I.4-8, I.4-9, 1.4-11, 1.4-12, 1.4-13, 1.4-16, f.4-22 and 1.4-23 at 300 ppm
showed over 75% mortality.

211
8. Activity against sifverleaf whitefly {bemisia argentifolii)
The active compounds were formulated in 50:50 acetone:water and 100 ppm Kinetic™
surfactant.
Selected cotton plants were grown to the cotyledon state (one plant per pot). The coty-
ledons were dipped into the test solution to provide complete coverage of the foliage
and placed In a well-vented area to dry. Each pot with treated seedling was placed in a
plastic cup and 10 to 12 whitefly adults (approximately 3-5 day old) were introduced.
The Insects were colleted using an aspirator and an 0.6 cm, non-toxic Tygon™ tubing
(R-3603) connected to a barrier pipette tip. The tip, containing the collected insects,
was then gently inserted into the soil containing ihe treated plant, allowing insects to
crawl out of the tip to reach the foliage for feeding. The cups were covered with a re-
usable screened lid (150 micron mesh polyester screen PeCap from Tetko inc). Test
piants were maintained in the holding room at about 25°C and 20-40% relative humidity
for 3 days avoiding direct exposure to the fluorescent light (24 hour photoperiod) to
prevent trapping of heat inside the cup. Mortality was assessed 3 days after treatment
of the plants.
In this test, compound 1.3-1,1.3-3, i.3-4,I.3-5,1.3-6, I.3-8, i.3-9, 1.3-10, 1.3-11,1.3-12,
1.3-13, 1.3-14,1.3-15, [.3-16, 1.3-17, 1.3-19,1.3-20,1.3-22, I.3-23, 1.3-25, I.3-26, I.3-27,
1.3-28,1.3-30,1.4-1, f.4-2 and I.4-3 at 300 ppm showed over 90% mortality.
9. Activity against Diamond back moth (plutella xylostella)
The active compounds were formulated in 50:50 acetone:water and 0,1 % (vol/vol)
Alkamuls EL 620 surfactant. A 6 cm leaf disk of cabbage leaves was dipped in the test
solution for 3 seconds and allowed to air dry in a Petri plate lined with moist filter paper.
The leaf disk was inoculated with 10 third instar larvae and kept at 25-27°C and 50-
60% humidity for 3 days. Mortality was assessed after 72 h of treatment.
In this test, compounds 1.1-1, 1.1-7,1.1-9,1.1-15,1.1-19, 1.1-21,1.1-24, 1.1-27,1.1-28,1.1-
29, 1.1-31, 1.1-32,1.1-45, 1.1-47, 1.1-61, 1.1-63, 1.3-5, 1.3-6, 1.3-7, 1.3-6,1.3-9, 1.3-10, I.3-
11, 1.3-12, 1.3-13,1.3-14, 1.3-15, 1.3-16, 1.3-17, 1.3-18, 1.3-19, I.3-20, 1.3-21, 1.3-22,1.3-
23, I.3-24, I.3-25, 1.3-26, I.3-27, 1.3-28, 1.3-29, 1.3-30, 1.3-31, I.3-32, I.3-33, I.3-34, I.3-
35, I.3-36, I.3-37, I.3-38, 1.3-39, 1:3-40, 1.3-41, I.3-42, 1.3-43, 1.3-44, I.3-45, I.3-46, 1.3-
47, I.3-48, i.3-49, 1.3-51, I.3-52, I.3-53, I.3-54, I.3-55, I.3-56, I.3-57, i.3-58,1.3-59, I.3-
60, 1.3-61, I.3-62, I.3-63, 1.4-1, i.4-2, i.4-3, I.4-4, I.4-5, I.4-6, i.4-7, I.4-8, I.4-9, 1.4-10,1.4-
11, 1.4-12, 1.4-13, 1.4-16, 1.4-17, 1.4-18, 1.4-19, and I.4-22 at 300 ppm showed over 75%
mortality.

212
10. Activity against Argentine ant {Linepithema humile), harvester ant {Pogonomyrrnex
californicus), acrobat ant (Crematogasterspp.), carpenter ant {Carnponotus fioridanus),
fire ant (Solenopsis invicfa), house fly [Musca domestics), stable fly (Sfomoxys calci-
trans), flesh fly {Sarcophaga sp.), yellowfever mosquito {Aedes aegypti/), house mos-
quito {Culex quinquefasciatus), malaria mosquito {Anopheles albimanus), German
cockroach {Blattella Germanica), cat flea (Ctenocephalides fells), and brown dog tick
[Rhipicephaius sanguineus) via glass contact
Glass vials were treated with 0.5 ml of a solution of active ingredient in acetone and
allowed to dry. insects or ticks were piaced into each vial together with some food and
moisture supply. The vials were kept at 22°C and were observed for treatment effects
in this test, compounds 1.3-4, 1.3-5 and I.3-6 at 10 ppm showed over 70% mortality of
yellowfever mosquito.
11. Activity against yellowfever mosquito {Aedes aegyptif), house mosquito {Culex
quinquefasciatus) and malaria mosquito {Anopheles albimanus) larvae via water treat-
ment
Well plates were used as test arenas. The active ingredient was dissolved in acetone
and diluted with water to obtain the concentrations needed. The finai solutions contain-
ing appr. 1 % acetone were piaced into each well. Approximately 10 mosquito larvae
(4ih-instars) in 1 ml water were added to each well. Larvae were fed one drop of liver
powder each day. The dishes were covered and maintained at 22°C. Mortality was
recorded daify and dead larvae and live or dead pupae were removed daily. At the end
of the test remaining live larvae were recorded and percent mortality was calculated.
In this test, compounds 1.1-37, 1.1-38, 1.1-49, 1.1-69, I.3-4, i.3-5, 1.3-6 and I.3-7 at 10
ppm showed over 70% mortality of yellowfever mosquito .
12. Activity against root-knot nematode {Meloidogyne incognita):
Test compounds are prepared and formulated into aqueous formulations using ace-
tone. Tomato plants (var. Bonny Best) are grown in the greenhouse in plastic tubs (4 to
6 plants per tub). The plants and soil (a 50:50 mixture of sand and "New Egypt" sandy
loam) are infested with -M. incognita J2 (to establish the "in-house" colony, M. incognita
J2 were initially acquired from Auburn University). The plants are kept pruned and are
used on an "as needed" basis. The tomato plants are kept in the cylinder containing
hydroponic solution and aerated until the nematodes are no .longer present in the solu-
tion (usually about 60 days). The cultures are checked daily by eluting a small volume
(approximately 20 ml) from the bottom of a funnel attached to the cylinder into a small

213
crystallizing dish and observed using a binocular dissecting scope. If needed for test-
ing, the nematodes are cleaned and concentrated by pouring the culture solution
through a sieve for cleaning and a sieve for concentrating. The nematodes are-then ;
resuspended in water to a concentration of approximately 20 to 50 nematodes per 50
ul. These are counted by putting 25 pi of the nematode solution into a well of an un-
used well of an assay plate. The total is then multiplied by 2 for a final total of nema-
todes per 50 ui of solution. To microtiter plates containing about 1.0 mg of compound,
80:20 acetone is added to each well and the solution is mixed to obtain the desired
compound concentration. The nematode solution is added to each plate. The plates
are then sealed and they are placed in an incubator at 27°C and 50% (+/-2%) relative
humidity. After 72 hours, the population mortality is read, whereby immobility of nema-
islnn Sr. nnr-rii „~ ,-.-.„L-i„r;i.,
IUUCO laicyaiucu aa mutuality.

214
Claims:
1. N-Thio-anthranilamid compounds of formula I

whertin
Rj is hydrogen; or Ci-Ci0-aikyf5 CrCio-alkenyl, CrCitralkynyl, or Ca-Ca-
cycioalkyl, each of which is unsubstltuted or substituted with 1 tot 5 groups
independently selected from halogen, cyano, nitro, hydroxy, Ci-Cig-alkox;
CrCiQ-aikylthio, Ci-Cio-aikylsulfinyi, d-Cio-alkylsutfonyl, C2-C10-
alkoxycarbonyl, Ci-Cio-alky lamina, di(Ci-Cio-alkyl)amino and CaCe-
cyqloalkylamino; or C'rCio-alkylcarbonyl, Ci-Cio-alkoxycarbonyf Ci-Cior
alkylaminocarbonyl, di(Ci-Cio-alkyl)arninocarbonyl;
A is a group selected from A' and A3

wherein
# denotes the binding site;
R* and R3 each independently are R6. -C(=G)R7, -C(=NOR7)R7, T
C(*NNR72)R7. -C(=G)OR7, _C(=G)NR7Z, -QC(=G) R7, -OC(=G)OR7. -
NR7C(=G)R7, -N[C(=G)R7]2, -NR7C(=G)OR7, -C(=G)NR7-NR72, rC(=G)NR7-
NR7[C(=G)R, -NR7-C(=G)NR72p -NR7-NR7C(-G)R7, -NR7-N[C(« N[(OG)R7]-NR72, -NRNRKOGJGR7], -NR7[(C=G)NR72, -NR7|C=NR73Rr,
-NR7{C=NR7)NR73l -G~NR72, -0-NR7(C=G)R7, ~S02NR72t -NR7S02R7, -
SQ2QR7, -OS02R7 -OR7, -URh, -SR7, -SIR73, -PR72, -P(=G)R7', -SOR7, -
SOaR7, -PG2R72j or -PG3R72; or
R2 and R3 together with the sulfur atom to which they are attaeh&d form a
saturated, partially unsaturated or unsaturated 3- to 8-membered ring which
contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur, which

215
ring can be fused with one or two saturated, partially unsaturated or unsatu-
rated 5- to 6-membered rings which may contain 1 to 4 heteroatoms se-
lected from oxygen, nitrogen, sulfur, wherein all of the above rings are un-
substituted or substituted by any combination of 1 to 6 groups Ra;
G is oxygen or sulfur;
R6 is C-Caralkyl, CVCo-aikenyi, Gj-Cao-alkynyl C3-Crcyc!aa!kyf, C-s-Cs-
cycloalkenyl, C3-Cs-cycfoalkynyi, phenyl, naphthyl, faipheny!, or a saturated,
partially unsaturated or unsaturated 3- to 8-membered ring system which
contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur, wherein
all of these groups are unsubstitutad or substituted by any comDisiatlon of 1
to 5 groups R&;
R7 is hydrogen or Rfl;
R3 is R3; or two groups R8 together with the atoms to which they are at-
tached form a saturated, partially unsaturated or unsaturated 3- to 8-
membered ring system which may contain 1 to 4 heteroatoms /hetero-
groups selected from oxygen, nitrogen, sulfur, SO and SC-2, and which ring
system Is unsubstituted or substituted with any combination of 1 to 6 groups
R9.
R9 is R'°, R«, -C(=G)R1a, -C(=NOR10)R10( -C(=NNR1(>z)R10 , -C(=Q)OR,
-C, -OC(=G)OR1°, -NR1°C(=G)R«, -N=G)R«]2, -
NRCGJOR™, -C(=G>NR-NR™2, -C(=G)NR-NRio[C(=G)R1a]1 -NR™-
C(=G)NR10z, -NR-NRCGJR10, -NR10-N[C(*G)RiG]g, -N[(C=G)R,0]-NR2,
-NR-NR"5[(C=G)GR10]I -NRl0[ NR1°{C=NR1°)NR102, -O-NR102, -0-NR1c(C=G}R1 -SO2NR102, -NR1°S02R1°,
-SO2OR10, -OSQ2R™, -OR10, -NR102, -SR«, ~S)Rl03, -PR10j, -P{=G)R1°, -
SOR10, -SO2R10, -PGaR102, ~PG3R102, or two groups R3 together are (*G),
(=N-R'0}, (*CR2), (=CHR), or (=CHz);
R10 is Ci-Cio-aiky), Cs-C-alkenyl, C2-Cio-alkynyl, Ca-Cs-cycldalkyl, C*-
Ca-cydoalkenyl, Cs-Cs-cycloalkyl- d-Ct-atkyl, C4-Ca-cydoaikeny.l-C1-C.i-
alkyl, QrCs-cydoalkyi-Ca-Calkenyl, CCe-cycloalkenyl-Ca-Ci-alkenyl, C1-
Cio-alkyl-Ca-Ce-cycloalkyl. C2-Cio-alkenyl-C3-Cs-cycloalkyl, C2-Cio-alkynyl-
C3-Ca-cycloalkyl, d-Cio-alkyl-C4-Ca-cydoalkenyl, Ca-Cio-alkenykCrCa-
cycloalkenyl, C2-Cio-alkynyl-C4-Ce-cydoaikenyl,
a saturated, partially unsaturated or unsaturated 3- to 8-membered ring sys-
tem which contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sul-
fur,

216
wherein the above groups are unsubstituted or substituted wfth any combi-
nation of from 1 to 6 groups R11;
R11 is halogen, cyano, nitro, hydroxy, mercapto, amino, formyl, .C.1-C10-
alkylcarbonyl, Ci-Cio-afkoxy, C2-Cio-aikenyloxy( C2-GiD-alkyny!oxy, CrCio-
haloaikoxy, Ca-Cio-haloaikenyloxy, CrCio-haloalkynyloxy, C3-Ce-
cycioaikoxy, CCa-cydoaikenyloxy, Ca-Cg-halocycloaJkaxy, CCa-
halocycloalkenytoxy, Cs-Ce-cycloalkyl- Ci-C4-alkoxy, C4-C8-cydoa)kenyl-C1-
C4-aikoxy, C3-Ga-cydaaJkys- CrCaikenyioxy, G4-G3'CycioaiksnylrCa-C4-
aikenyloxy, Ci-Cio-aityl-Cs-Ca-cydoaikoxy, CrCio-alkenyl-Ca-Ce-
cycioaikoxy, G-i-Gio-aikynyl-Cs-Ca-cydoalkoxy, Ci-Cio-alkylCs-Cs-
cycloalkenyloxy, CCio-alkenyl-Ca-CB-cycloafksnytoxy, Ci-Gt-alteoxy-Cr
Cio-aikoxy, CrCaikoxy-Cz-Cialksnyioxy, mono- or di(Ci-Gi5-
a!ky!)carbamoy!. mono- or di(Ci-CiQ-haloa[kyJ)carbamoyl, mono- or di(C3-
Gs-cycloa[kyi)carbamoyl.
Ci-Gia-alkoxycarbony!, Cs-Ca-cydoaikoxycarbonyl, Ci-do-alkylcarbonyloxy,
Ga-Ca'CycIo aikyfcarbonyloxy, C,-Cio-haioalkoxycarbonyl, Ci-do-
haioalkylcarbonyloxy, Ci~Cio-a!kanamido, Ci-Cio-haloalkanarnJde, C£-CtQ-
alkenamido, Cs-Caydoalkanamido, CHa-cydoalkyl-Ci-C-alkapamido,
Ci-Cio-aikylthio, C2-Cio-a!kenyIth!0, Ca-C10-a!kynylthio, CrCio-halbaikylthio,
C2-Cio-haloalkenyithio] C2-Cio-haloalkynylthio, Ca-Ca-cydoalkylthip, C3-CB-
cydoalkenyithio, Cs-Ca-hafocycloalkylthio, Ca-Cs-halocycfoafkenyithio, C3-
Cs-cydoalkyi-Ci-C4-alkyithio, Ci-Ce-cycloalkerryi-Ci-Caikyitliio,-,C3"Ce-
cycloalky!- Ca-CalkenySthio, C4-Ce-cydoa!kenyi-C2-C.t-alkenylthio, C1-C10-
aIkyt-C3-Ce-cycloalkylthio, Ci-Cio-alkenyl-Ca-Ca-cycioalkylthio, CiCio-
aikynyl-Cs-Ca-cycioalkylthio, Ci-Cio-alkyl-C3-Cs-cycloaIkeny[thio, C1-C10-
aIkenyl-C3-Ca-cyctoafkeny[thio, Ci-Cio-alkylsulfinyl, Cz-do-atkenylsulfinyl,
Cz-Cio-aIkynyfsulfinyl, Ci-C10-haloa}kylsulfinyl, Ca-Cicrhaloalkeny&ulfinyl,
Cj-Cio-haloalkynylsulfinyl, Cs-Ca-cydoalkylsulfiny!, C3-C8-
cydoalkenylsulfinyl, Cj-Cs-halocycioalkySsuifinyi, Ca-Cs-
halocydoalkenylsulfinyl, Ca-Ca-cycloalkyl- Ci-Calkyisuifmyi, C4-GB-
cycloalkanyl-CrCalkyisulflnyl, C3-Cs-cydaaIky[- CCaSkenyl'sLiEflnyl, C4-
Cs-cycloalkenyi-Cj-Ci-alkenylsuifinyl, Ci-Cio-alkyf-Ca-Ce-cydoalkylsulfiny!,
CrCi6-alkenyl-C3-CB-cycloalkyIsulfinyl, Ci-Cio-alkynyl-Ca-Ca- ;
cycioaikyisuifinyl, GrCio-alkyKVGa-cycioalkenylsulfinyS, Ci-Cio-alkeny!-C3-
Cs-cycioalkertylsulfinyl, Ci-Cio-a!ky!su[fony!, CCio-alkenylsuifonyl, Cg-C-te-
alkynylsutfony!, Gi-Cio-haloaikylsu)fonyl, Ca-Cio-haloalkenylsulfonyl, C2-C10-
haloalkynyisuifonyl, C3-Ca-cyc!oaIkylsuifonyl, Cs-Cs-cycloalkenylsuffonyl, C3-
Cg-halocycloaikylsulfonyl, Cs-Cs-halocyctoalkenylsulfonyl, Ca-Cs-cydoalkyl-
Gi-C4-a!ky!suifonyl, C C2-C4-alkenyIsuifonyl, C4-Cs-cydoalkenyl-C2-C4-alkenyisutfonyl, GCKJ-
a!kyhC3-Cs-cydoalkylsulfonyi, Ci-Cio-alkenyl-Ca-CB-cydoalkyisurtonyl, CI-
Cio-alkynyl-Ca-Ca-cydoafkylsuffonyi, Ci-CiQ-aikyl-Ca-Ca-cycloaikenyfsulfonyf,

217
Ci-Cio-alkenyl-Ca-Ca-cycloalkeriylsuifony!, di(Ci-Cio-alkyI)amino, -CrCio-
atkyiamino, C2-Cio-a!kenytamino, C2-CiQ-alkynyIamino, Ci-Cio-alfeyf-Og-Cio-
aikenylamino, Ci-Cio-alkyl-Ca-Cio-afkynylamino, CrCio-haioaikyTarnino, Cs-
Cia-haloalkenylamino, Cs-G-hatoalkynylamino, Cs-Ca-cycloaikylamino, C3-
Cs-cyctoaikenylamino, C3'CB-halocycloalkylamino, Ca-Cs-
halQcycloalkenylamino, C3-C3-cycioalkyl- CrC4-alky!amino, C4-Ca-
cycloalkenyl-C,-C4-alky!aminor C5-Ca-cycloalkyi- CCaJkenylaitiino, GrCa-
. cyc)oalkeny!-Cs-C4-a]kenylamlno, Gi-Cio-aiky!-C-3'Ca-cyc!oalky!rnino, C-
Gio-alkenyi-Cs-Crcycloalkylamino, CrCio-alkynyl-Ca-Ce-cycloalkylamino,
Gi-Gio-a!kyl-C3-CB-cycloalksnylamino, Gi-Cio-a!kenyi-Ca-Ca-
cyctaalkenylamina,
tri(CrCic-aiky!)si[y!, aryl, aryioxy, arylthlo, aryiarnino, aryl-Gi-Ca-aikoxy, aryl-
Ca-Calkenyloxy, aryl-d-Oaikylthio, aryi-C2-C4-aikenyithio, aryt-Ci-C«-
alkylamino, aryl-Ca-C4-alkenyiamino, aryl-di{Ci-C4-alkyO'silyi, triaryisHyi,
wherein ary! is phenyl, naphthyl or biphsnyi, or
a saturated, partially unsaturated or unsaturated 3- to g-membemd ring sys-
tem which contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sul-
fur,
wherein these ary! and these heterocyclic ringsysterns are unsubstituted or
substituted with any combination of from 1 to 6 groups selected from halo-
gen, cyano, nitro, amino, hydroxy, msrcapto, C-i-Gi-alkyi, Ci-C4-ha!o3lkyl,
C3-C6-cydoalkyI, Ci-C4-a!koxyT Ci-C-haloatkoxy, Ci-C4-a!kyithio? G1-C4-
haloalkylthio, di(Gi~C4-alky0amino, Ci-G4-aikylamino, Ci-C4-haloalkylamino,
formyl and Ci-C4-alkylcarbonyl;
R* is NRR13;
R12 and R13 are each independently hydrogen; or C-i-Czo-alkyf, C-Czo-
aikenyJ or Gs-Cio-alkynyl, each of which is unsubstituted or substituted with
any combination of 1 to 6 groups selected from d-Calkoxy, CirC4-
alkylthio, cyano, nitro, formyi, CrC4-alkylcarbonyl, Ci-C4-a!koxyc;arbonyl,
Ci-C-alkyiaminocarbonyl, di{CrG4-alkyi)arhinocarbonyl, Ci-C-alkylsulfinyi,
d-C-alkylsuifonyl, C3-Ca-cycloalkyl, and phenyl, wherein phenyl itself is
unsubstituted or substituted by 1 to 4 substituents selected fronr.halogen,
Ci-C4-aikyl, Ci-C4-aikoxyI Ci-C4-fluoroa!kyl, Ci-C-aikyioxycarbo'nyl,
trifluoromethylsuifonyl, formyi, nitro and cyano; or
Ci-Co-haioalkyi, Ca-Cao-haloalkenyl, C2-C2D-haloa!kynyi, C5-C10- •
cycloaikenyf, or a saturated or partially unsaturated or unsaturated 3- to 8-
membered ring system which contains 1 to 4 heteroatoms selected from
oxygen, nitrogen, sulfur, or phenyl or naphthyi, wherein this ring system and
phenyl or naphthyl themselves are unsubstituted or substituted by 1 to 4

218
substituents selected from halogen, Ci-C4-afkyl, d-d-alkoxy, d-d-
fiuoroalkyl, d-Ct-afkyloxycarbonyl, trifluoromethylsulfonyi, formyl, nitro and
cyano; or
R12 and R13 together with the nitrogen atom to which they are attached form
a saturated or partially unsaturated 5- to 8-membered heterocycle which
besides the one nitrogen atom contains 0 fo 2 further heteroatoms selected
from oxygen, nitrogen, sulfur, and may contain 1 or 2 carbonyl groups or
thiocarhonyl groups and which Is unsubstituted or substituted by from 1 to 4
groups selected from d-C-alkyl, d-C4-alkoxy and d-C4-haloalkyl;
RS is hydrogen; or d-Cao-alkyf, d-Cao-aikenyi, C2-C3o-alkynyi, d-d-
alkylcarbonyl, d-d-aikylaminocarbonvl. d-d-alkoxvcarbony! each nf
which is unsubstituted or substituted by from 1 to 6 groups selected from
d-d-alkoxy, d-CaikyJthto, cyano, nitro, formy!, d=C4=alkyfcarbonyl, d-
d-aikoxycarbonyl, d-d-alkylaminocarbonyl. di(d-dr
alkyOaminocarbonyl, d-d-aikyfsuffinyl, d-C4-alkylsulfonyl, C*-Ca-
cycioalkyl, and phenyl, wherein phenyl itself is unsubstituted or substituted
by 1 to 4 substituents selected from halogen, d-d-alky}, Ci-CValkoxy, d-
d-fluoroalkyi, d-d-alkyloxyearbonyi, trifluoromethylsulfonyi, formyl, nitro
and cyano; or
d-Goo-haJoaiky!, Ca-Cao-haioalkenyl, Os-Czo-haJoalkynyl, Crdo-
cydoalkenyl, or a saturated or partially unsaturated or unsaturated 3-to 6-
membered ring system which contains 1 to 4 heteroatoms selected from
oxygen, nitrogen, sulfur, or phenyl or naphthyl, wherein this ring system and
phenyl or naphthyl themselves are unsubstituted or substituted by! 1 to 4
substituents selected from halogen, d-d-a'kyl, d-d-afkoxy, C1-C4-
fluoroalkyl, d-d-alkyloxycarbonyl, trifluoromethylsurfonyf, formyl; nitro and
cyano;
Q1 and Q2 each independently are hydrogen, halogen, cyano, SCN, nitro, hy-
droxy, d-do-alkyl, d-Cio-haloaikyl, C2-Cnralkenyl, d-da-haloalkenyl, d-
Cio-aikynyl, d-do-haloalkynyl, d-Ca-cycloalkyl, Cs-Cs-haiocycioalkyf, Cr
do-aikoxy, d-do-haloa!koxyt Ci-do-alkylthio, d-do-haloalkylthio, C1-C10-
aikylsuifinyl, d-do-haloalkylsulfinyl, d-Cio-alkylsulfonyl, Crdo-
haloalkylsulfonyl, d-do-alkylsulfony!oxy, Ci-Cio-haloalkylsulfonyloxy, Cr
do-alkylamino, di{d-Cio-alkyl)amino, d-Ca-cyclalkytamino, alkylcarbonyl,
Ci-do-alkoxycarbony!, d-do-aikylaminocarbonyl, di(d-d alkyl)aminocarbonyf, ortri(d-do)-alkylsi!yl, or

219
Q1 and Qz are each independently phenyl, benzyl or phenoxy, wherein each ring
is unsubstituted or substituted with any combination of from 1 to 3 substitu-
ents independently selected from the group halogen, cyano, ni,trof C1-C10-
alkyl, Ci-Cio-haloalkyl, C2-CiQ-alkenyl, Cg-Cio-haloaikenyl, Ca-Cio-alkynyl,
C3'Cio-haioalKyny!» Ca-Ca-cycloaikyl, Ca-CB-halocycloaikyl, Ci-do-aJkoxy,
CrCio-haloafKoxy, Crdo-alkylfriio, Ci-Cio-alkyisulfinyl, CrCio-alkylsuifony],
O-Cho-alkyiamino, di(Ci-Cio-alkyi)amino, Ca-Ca-cycloalkylamino, C1-G10-
.aikyf-Ca-Ca-cycioalkyiamino, GrCio-aikylcarbonyl, Ci-Cio-alkoxycarbonyl,
Ci-Cio=alkyfaminocarbonyl, d!(Ci-Cio-alkyl)artiJhocarboriyi and trKCrCio)-
aikylsilyl;
Q3 is halogen; or Ci-do-alkyi, Ci-Cto-haloalkyl, Ca-Cio-alkenyl, CZ-CKT
haloaikenyl, C2-Cio-a!kynyl, Ca-Cio-haloalkynyi, Cs-CB-cycloa!kylT. C3-Ca-
haiccycloalkyi, Ci-Cio-aikyl-Cs-Cs-cycIoalkyl, Ci-Oia-haloalkyi-GafCfl-
cycloafkyi, each unsubstituted or Independently substituted with $ to 2
groups selected from cyano, Ci-Cia-afkoxy, C',-Cio-haioa!kcxy, O1-C10-
aikyithio, Ci-Cio-hatoalkyfthlo, Ci-Cio-alkylsulfinyl, Ci-Cio-haloa!kyisulfinyi,
Ci-Cio-aikylsuIfonyl, Ci-Cisrhaloalky!sulfony1, and Ci-Cio-alkoxycarbonyl; or
Q3 is OR«, StOJqR1* NR15R1S, 0S(O)2R«, NRieS C(Rie)=NOR1«rC3-C8-cycloa!ky]-C1-C4-a!kyllCi-Cio-a!kylarninothiocarbonyl,
or di(Ci-Cio-alkyl)aminothiocarbonyI;
W* is d-CValkyl, CrCia-haloalkyi, Cs-Cio-aikenyi, Ci-C-halo.aikenyl, C3-
Cio-alkynyi, Ca-Cio-haloalkynyl, C3-CB-cycioalky1, Ca-Ca-halocycloalkyl, C3-
C6-cycloalkyl-Ci-C4-alkyl, Ci-C4-alkyl-C3-Cs-cycloalkyl, Ca-Ca-hajdcycloafkyl-
Ci-C4-alkyl, CrC4-haloalkyl-Ca-Cs-cycloalkyi, or Ci-Cio-haloalkylcarbonyl,
each unsubstituted or substituted with 1 R19;
R15 is GCio-alkyi, d-Cio-haioaikyl, C2-Cio-aikenyl, C2-Cio-ha!oa)kenyl, C2-
Cio-alkynyi, Ca-CiQ-haloalkynyl, Cs-Ce-cydoalkyl, Cs-Ca-halocycloalkyl, C1-
Ci-alkyl-C3-Ce-cycloalkyI, Ci-C haloalkylcarbonyl, each unsubstituted or substituted with 1 R19;
R™ is hydrogen; or Ci-Cio-alkyi, CrCto-hatoalkyl C2-Cio-a(kenyl, Ca-C-
haloaikenyl, C2-C1D-alkynylj Ca-Cio-haloalkynyl, Ca-Ce-cycloalkyl, C3-C9-
halocycloalkyi, CrCa-alkyt-Ca-Ca-cycioaikyl, or C1-C4-haloalkyi-C3-.Cs-
cycloalkyl, each unsubstituted or substituted with 1 R,s;
R17 is Ci-do-alkyl, CrCia-haloalkyl, C2-Cto-a!kenyi, Ca-Cio-haloalkenyf, C2-
Cio-aikynyl, Cj-Cia-haloaikynyl, Cs-Ca-cydoalkyl, Ca-Ca-halocycloalkyl, C1-

220
Gralkyl-C:j-Ce-cyc]oalkyf, or Ci-C4-haloalkyl~C3-Cs-cycloaifcyl, each unsubs-
tituted or substituted with 1 R18;
Rie is cyano, nitro, d-do-alkoxy, Ci-Curhaloalkoxy, CrCio-alkylthio,
C,-Cio-haioaikylthio, Ci-Cio-aifcyisuififiyi, Ci-Cio-haioa!Ky|!sulfinyl,
Ci-do-aikylsulfonyl, Ci-Cio-haloafkylsulfcnyl, C1-C10- ]
alkoxycartaonyi, Gi-Cio-aikyiamlnG, or di(Ci-Cio-a!ky!)ammo; or
R19 is phenyl or a heteroaromatic- 5= or 6=membered ring whiph contains
1 to 4 heteroatoms selected from oxygen, nitrogen, suifdr, the
phenyl radical and the heteroaromatic ring bsing unsubstftuted or
substituted with any combination of from 1 to 3 groups selected
from haloaen cvartn. nitrn. Hi-Gin-sikvi r-fft-halnatkul' Cn-C
afkenyi, Cz-Cio-halosiksnyl, C2-Cic=s!kyny!l Ca-CiQ-haioaikynyl, C3-
Ca-cycloalkyl, Cs-Ca-halocycloalky!, Ci-Cie-alkoxy, Ci-Cis-
haioalkoxy, Gi-Curalkylthio, Gi-G-fo-aikyisuifinyi, Ci-Cie-
alkylsulfonyl, CrCio-alkyiamino, di(Ci-Cio-alkyl)amino, Qa-Cs-
cycloalkyiamino, CrCio-alkyi-C-Ca-cycloaikylamino, C1-C10-
alkylcarbonyl, Gi-Ci di{Ci-Cto-ail R16 is the same or different: hydrogen, Ci-Cio-alkyl, or d-CiD-haipalkylr
q is 0, 1 Of 2;
Q4 is halogen, cyano, nitro, hydroxy, COOH, C(G)NHZ, Ci-Cio-alkyl, C1-C10-
haloaikyl, Ca-Gio-alkenyi, Cs-Cio-hafoalkenyl, Cz-Cio-aikynyl, C3-Ci(r
haloalkynyf, C3-Ce-cycloalkyi, C3-Ce-haiacycloalky!, Ci-Cio-alkoxyi C1-C10-
haioaikoxy, Ci-Cio-alkyithio, Ci-C-io-haioatkylthio, Ci-Ci0-alkylsulfiny!, Ci-
Cio-haloalkylsulfinyl, Ci-Cio-alky[su!fonyf, CrCio-foaloaikylsuifonyi, Ci-Cicr
aikyiamino, di(Ci'Cia-alkyi)amino, C3-Ca-cycioa!kyiamino, C1-C10-,
alkylcarbonyl, Ci-Ci alkyf)ammocarbony! or tri(Ci-CiQ)-aikyJsi!yl; or
Q" is phenyl, benzyl, benzytoxy, phenoxy, a 5- or S-membered heterejaromatic
ring which contains 1 to 4 heteroatoms selected from oxygen, nitrogen, suf-
fur or an aromatic 8-, 9- or 10-mernbered fused heterobicyclic ring system
which contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur,
wherein each of the above ring systems is unsubstftuted or substituted with
any combination of from 1 to 3 groups selected from halogen, cyano, nitro,
Ct-Cio-alkyl, Ci-Cio-haloalkyl, Ca-Cio-aikenyl, C2-Cio-haioalkenyl, C2-Cicr
alkynyl, C3-Cto-haloalkynyl, Cs-Ca-cycloalkyl, C3-Ce-halocycloalkyl, Ci-Cl0-

221
alkoxy, d-Cio-Jialoalkoxy, Ci-C,o-a!kyIthio, Ci-Cio-alkylsulfin>fi, C-Cio-
alkylsulfonyl, C-t-Cia-aSkylamina, di(C.i-Cio-alkyl)amino, Cj-Ca- '
cycloalkylamino, Ci-Cio-alkyi-CVCe-cycioaikyJamino, GrCuralkylcarbonyl,
Ci-Cio-alkoxycarbonyl, Ci-Cto-alkylaminoGarbonyl, di{Ci-Cio-
alky!)amincxsFbonyl and fri(Ct-C10)-aikylsilyl;
X and Y are each Independently oxygen or sulfur;
V and V are each independently N or CQ2;
'•fit ' m Is 2;
n isGorl;
p is 0, 1,2, 3, or 4;
or the enanii'omers or salts or N-oxides thereof.
2. N-Thio-anthranilamlcf compounds of formula i according to claim 1 wherein
X and Y are oxygen.
3. N-Thio-anthranilamid compounds of formula I according to claims 1 or % wherein
V and V are CH.
4. N-Thio-anthranffamid compounds of formula J according to claims 1 to 3 wherein
W isN;
RT is hydrogen or Ci-Gt-aikyl;
Q1 is halogen, cyano, SCN, nitro, hydroxy, Ci~Cia-a!kyl, CT-Cicrhaloalkyi, C3-C3-
cycloalkyi, Ct-Cio-alkoxy, Ci-C-icrhaloalkaxy, Ci-CiQ-alkylthio, C1-C10-
haloafkyithio, Ci-dg-alkylsulfonyl, Ci-do-afkylsulfonyioxy, Ci-Ci0-a!kyfamino
or di(Ci-Cio-aIkyl)amino;
Q* is halogen, cyano, SCN, nitro, hydroxy, Ci-Cio-alkyI, Ci-C-KrhaJoalkyl, Ci-Cs-
cycfoalkyf, Ci-Cio-alkoxy, C-rCi0-haloalkoxy, C,-Cio-alkytthio, Ci*C«r
haloalkyfthio, CrCio-alkylsuifonyl, Crdtralkylsulfonyloxy, Ci-Cicraikylamino
or di(Ci-Cio-alkyl)amino;

222
Q3 is halogen, Ci-Cio-alkyl, Ci-Cio-haloalky!F C2-Cio-alkynyl, C3-Ce-cytpIoaikyJ,
Ca-Ca-haiGGycloafkyf, each unsubstituted or independently substituted with 1
to £ groups selected from cyano, Ci-Cio-alkoxy, Ci-C1o-halQalkbxy;orCrCi&-
alkylthia, or
Q3 is OR14, S(0)qR14, NR15R16, QS(0)2R17, C(S)NHa( C(R13)=NOR19; wherein
H14 is Gi»Cio-aiky! or Ga-Cs-eycioaikyi unsubstituted or substftuted:,Wlth 1 R'18;
and
R15 \B Ci-Cio-a!ky!, CrCio-haloalkyl. C2-Cio-a[keny!. C2-Cio-s!kyny!; each.un-
substrtuted or substituted with 1 R1S; and
RIS js hydrogen, Ci-CtD-atkyf. Gi-Cia-haloaSkyl, Ca-G-alkenyl, Ca-Cie-
aikynyl, each unsubstituted or substituted with 1 R19; and
R17 is Ct-Cio-aikyi, Ci-Cio-halealkyi, C2-Ci cycloalky!, each unsubstituted or substituted with 1 R1S; and
.R«f3 ':
W* is cyano, nitro, Gi-Cio-alkoxy, Ci-Cio-haloa!koxy, Ci-Cio-alkyfthl©, C1-C10-
haloaikyithio;
Q4 is halogen, cyano, nitro, C-t-Cio-alkyi, Cro-haloalkyl, Ci-Cio-alkoxy, C1-C10-
haloalkoxy, CrCio-alkylthio, Ci-Ci0-haioalky!thio, Ci-Cio-a!kylsulfinyl, CrCiQ-
haloalkylsulflnyl, Ci-Cio-alkylsulfony], Ci-Cio-haloalkyisuifonyl, or Q1-C10-
alkoxycarbonyf, and is in the ortho-position; and
p isl
N-Thio-anthranilamid compounds of formula I according to claims 1 to 4 wherein
W is N;
R1 is hydrogen;
Q1 is hydrogen, halogen, cyano, Ci-CValkyl or Ci-C4-haloalkyi;
Q2 is halogen, cyano, Ci-CValkyl or CrChaloalky];
Q3 is halogen, CrC4-haloafkyl or Ci-C4-haioalkoxy;

223
Q4 is halogen or C-rCrhaloaikyi and is in the ortho-position; and ;
p is 1.
6. N-Thio-anthranilamid compounds of formula I according to claims 1 to S wherei
A is A1; '
R3and R3 each Independently are is Gi-do-afkyl, C2-Gio-aik@nyl, Ga-C-to-ajkyn)
Ca-Cvcycloalkyl, or phenyl, whersin these groups are unsubstituied or sub
stituted by any combination of 1 to 6 groups selected from R11, •
R" is halogen, eyano, nitro, hydroxy, mercapto, amino, Ci-CHn-alkaxy, Cr
Cio-haloalkoxy, Ca-Gg-cycioalkoxy, C-s-Gio-aSkoxycarbonyl, Ci*Gio-
alkylcarbohyioxy. Ci-Cio-alkahamido, CrCio-aikylthla, Ci-Cio-alkylsulfinyl,
GrCio-atKyisuifonyi, di(Ci-Gio-aikyi)amino or Gi-Cio~alkyiamino; pr
R2 and R3 together with the sulfur atom to which they are attached form a unit
SR2Ra of the following formula:

wherein
r isOoM;
D is a direct bond, branched or straight d-Galkytehe, 0, 3{0)aijz or
NRJ, preferably CH2, O, or NRJ;
R9 is as defined above;
R) is hydrogen, d-Ct-alkyl, Ci-C4-aikyIcarbonyl, Ci-C4-alkoxycarbonyl,
Ci-C-alkylaminocarbonyl, di(Ci-C4-alkyl)aminocarbonyI, or Ci-C4-
alkylsulfonyl;
a,b are the same or different 0,1, 2, 3 or 4, preferably 0,1, or 2,
7. N-Thio-anthraniiamid compounds of formula I according to claims 1 to,5 wherein
A is A2;
R« isNRRand
R12and R13 are each independently hydrogen, Ci-C2o-alky1, CCjcralkenyl or
i C2-C2o-alkynyl, each of which is unsubstituted or substituted by from 1 to 3
CM, Ci-C2o-hatoalkyl, or R12 and R" together with the nitrogen atop? to which

224
they are attached may also form a saturated or partially unsaturated 5- to 9-
membered heterocycie which besides the one nitrogen atom contains 0 to 2
further heteroatoms selected from oxygen, nitrogen, sulfur, and r/iay contain
1 or 2 carfaonyl groups or thiocarbonyl groups and which is uns'ubstftuted or
substituted by from 1 to 4 groups selected from Ci-C4-alkylp Oi-G4-aikoxy anc
CrCt-ftaloalkyl;
Rs is hydrogen.
8, A process for the preparation of compounds of formula (J-1)

wherein the variables are as defined for formula (!) in claim 1, characterized in
that an activated derivative of a carboxylic acid of the formu/a m
wherein the variables are as defined for formula (I) is reacted in the presence of a
base with a compound of the formula AT-H or A*-H, respectively.

wherein the variables are as defined for formula (i).
9. A process for the preparation of compounds of formula (I-2)

225

wherein the variables am as defined for formula (!) in claim 1, characterized in
that an amid© of the formula (IV)




wherein the variables are as defined for formula (i) in ciaim 1f is reacted with a
sulfoxide of the formula (V),
wherein R2 and Raare as defined for formula (I) in ciaim 1, in the presence of a
condensating agent.
10. Use of compounds of formula I as defined in claims 1 to 7 for combating insects,
acarids, or nematodes.
11, A method for the control of insects, acarids or nematodes by contacting the in-
sect, acarid or nematode or their food supply, habitat, breeding ground or their
locus with a pesticidally effective amount of compositions or compounds of for-
mula I as defined in claims 1 to 7.
12, A method of protecting growing plants from attack or infestation by insects,
acarids or nematodes by applying to the foliage of the plants, or to the. soil or wa-
ter in which they are growing, a pesticidaliy effective amount of compositions or
compounds of formula i as defined in claims 1 to 7.
13. A method for treating, controlling, preventing or protecting animals against infes-
tation or infection by parasites which comprises orally, topically or parenteral
administering or applying to the animals a parasiticsdaliy effective amount of
compositions or compounds of formula I as defined in claims 1 to 7 or their enan-
tiomers or veterinary acceptable salts.

226
14, A process for the preparation of a composition for treating, controlling, (preventing
or protecting animals against infestation or infection by parasites which com-
prises a parasiticidaify effective amount of compositions or compounds of for-
mula I as defined in claims 1 to 7 or their anantlomers or veterinarily acceptable
salts,
15. Compositions comprising a pesticidally or parasiticidaily active amount of com-
pounds of formula I as defined in claims 1 to 7 and ari agronomicaiiy or vetarinar-
iiy acceptable carrier.







N-Thio-anthranilamid compounds of formula (I)
wherein A is a group selected from A1 and A2
wherein the variables and the indices are as defined per the description, processes for
preparing the compounds I, pesticidal compositions comprising compounds I, use of
compounds I for the control of insects, acarids or nematodes, and methods for treating,
controlling, preventing or protecting animals against infestation or infection by parasites
by use of compounds of formula I.

Documents:

http://ipindiaonline.gov.in/patentsearch/GrantedSearch/viewdoc.aspx?id=43lSCKOva58nk6rtoqQPAw==&loc=wDBSZCsAt7zoiVrqcFJsRw==


Patent Number 272397
Indian Patent Application Number 5002/KOLNP/2007
PG Journal Number 14/2016
Publication Date 01-Apr-2016
Grant Date 31-Mar-2016
Date of Filing 24-Dec-2007
Name of Patentee BASF SE
Applicant Address 67056 LUDWIGSHAFEN
Inventors:
# Inventor's Name Inventor's Address
1 PUHL MICHAEL BURSTADTER STR 95, 68623 LAMPERTHEIM
2 SCHMIDT, THOMAS PFARRGASSE 8, 67433 NEUSTADT
3 DICKHAUT JOACHIM KLEINE LOBINGSGASSE 4/3, 69121 HEIDELBERG
4 BASTIAANS HENRICUS MARIA MARTINUS BARTHOLOMAEUS-ARNOLDI-STR 35, 61250 USINGEN
5 BRAUN FRANZ-JOSEF 3602 LONG RIDGE ROAD, DURHAM, NC 27703
6 OLOUMI-SADEGHI HASSAN 12105 PAWLEYS MILL CIRCLE, RALEIGH, NC 27614
7 RACK MICHAEL HILDASTR 11/1, 69214 EPPELHEIM
8 CULBERTSON DEBORAH L 6400 VINTAGE RIDGE LANE, FUQUAY VARINA, NC 27526
9 ANSPAUGH DOUGLAS D 4007 WINECOTT DRIVE, APEX, NC 27502
10 BUCCI TONI 2629 HIDDEN MEDOW DRIVE, FUQUAY VARINA, NC 27526
11 COTTER HENRY VAN TUYL 8329 LAKEWOOD DRIVE, RALEIGH, NC 27613
12 KUHN DAVID G 1208 DALGARVEN DRIVE, APEX, NC 27502
PCT International Classification Number C07D 401/04
PCT International Application Number PCT/EP2006/063761
PCT International Filing date 2006-06-30
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 60/697166 2005-07-07 U.S.A.