N-thio-anthranilamid compounds and their use as pesticides
N-Thio-anthranilamid compounds of formula (I) wherein A is a group selected from A 1 and A 2 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.
1. A compound of formula I having the following structure,
wherein,
R 1 is hydrogen;
A is
wherein, * denotes the binding site,
n is 0 or 1;
R 2 and R 3 each independently are R 6 , —C(=G)R 7 , —C(═NOR 7 )R 7 , —C(═NNR 7 2 )R 7 , —C(=G)OR 7 , —C(=G)NR 7 2 , —OC(=G)R 7 , —OC(=G)OR 7 , —NR 7 C(=G)R 7 , —N[C(=G)R 7 ]2, —NR 7 C(=G)OR 7 , —C(=G)NR 7 —NR 7 2 , —C(=G)NR 7 —NR 7 [C(=G)R 7 ], —NR 7 —C(=G)NR 7 2 , —NR 7 —NR 7 C(=G)R 7 , —NR 7 —N[C(=G)R 7 ] 2 , —N[(C=G)R 7 ]-NR 7 2 , —NR—NR 7 [(C=G)GR 7 ], —NR 7 [(C=G)NR 7 2 , —NR 7 [C═NR 7 ]R 7 , —NR 7 (C═NR 7 )NR 7 2 , —O—NR 7 2 , —O—NR 7 (C=G)R 7 , —SO 2 NR 7 2 , —NR 7 SO 2 R 7 , —SO 2 OR 7 , —OSO 2 R 7 , —OR 7 , —NR 7 2 , —SR 7 , —SiR 7 3 , —PR 7 2 , —P(=G)R 7 , —SOR 7 , —SO 2 R 7 , —PG 2 R 7 2 , or —PG 3 R 7 2 ; or
R 2 and R 3 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, wherein all of the above rings are unsubstituted or substituted by any combination of 1 to 6 groups R 8 ;
G is oxygen or sulfur;
R 6 is C 1 -C 20 -alkyl, C 2 -C 20 -alkenyl, C 2 -C 20 -alkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl, C 3 -C 8 -cycloalkynyl, phenyl, naphthyl, biphenyl, 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 unsubstituted or substituted by any combination of 1 to 6 groups R 8 ;
R 7 is hydrogen or R 6 ;
R 8 is R 9 ; or two groups R 8 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 heteroatoms/heterogroups selected from oxygen, nitrogen, sulfur, SO and SO 2 , and which ring system is unsubstituted or substituted with any combination of 1 to 6 groups R 9 ;
R 9 is R 10 , R 11 , —C(=G)R 10 , —C(═NOR 10 ), —C(═NOR 10 )R 10 , —C(═NNR 10 2 R 10 , —C(=G)OR 10 , —C(=G)NR 10 2 , —OC(=G)R 10 , —OC(=G)OR 10 , —NR 10 C(=G)R 10 , —N[C(=G)R 10 ]2, —NR 10 C(=G)OR 10 , —C(=G)NR 10 —NR 10 2, —C(=G)NR 10 —NR 10 [C(=G)R 10 ], —NR 10 —C(=G)NR 10 2 , —NR 10 —NR 10 C(=G)R 10 , —NR 10 —N[C(=G)R 10 ] 2 , —N[(C=G)R 10 ]—NR 10 2 , —NR 10 —NR 10 [(C=G)GR 10 ], —NR 10 [(C=G)NR 10 2 , —NR 10 [C═NR 10 ]R 10 , —NR 10 (C═NR 10 )NR 10 2 , —O—NR 10 2 , —O—NR 10 , —SO 2 NR 10 2 , —NR 10 SO 2 R 10 , —SO 2 OR 10 , —OSO2R 10 , —OR 10 , —SR 10 , —SiR 10 3 , —PR 10 2 , —P(=G)R 10 , —SOR 10 , —SO 2 R 10 , —PG 2 R 10 2 , —PG 3 R 10 2 , or two groups R 9 together are (=G), (═N—R 10 , (═CR 10 2 ), (═CHR 10 , or (═CH 2 );
R 10 is C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl, C 3 -C 8 -cycloalkyl, C 4 -C 8 -cycloalkenyl, C 3 -C 8 -cycloalkyl-C 1 -C 4 -alkyl, C 4 -C 8 -cycloalkenyl-C 1 -C 4 -alkyl, C 3 -C 8 -cycloalkyl-C 2 -C 4 -alkenyl, C 4 -C 8 -cycloalkenyl-C 2 -C 4 -alkenyl, C 1 -C 10 -alkyl-C 3 -C 8 -cycloalkyl, C 2 -C 10 -alkenyl-C 3 -C 8 -cycloalkyl, C 2 -C 10 -alkynyl-C 3 -C 8 -cycloalkyl, C 1 -C 10 -alkyl-C 4 -C 8 -cycloalkenyl, C 2 -C 10 -alkenyl-C 4 -C 8 -cycloalkenyl, C 2 -C 10 -alkynyl-C 4 -C 8 -cycloalkenyl, a saturated, partially unsaturated or unsaturated 3- to 8-membered ring system which contains 1 to 4 heteroatoms selected from oxygen, nitrogen, sulfur, wherein the above groups are unsubstituted or substituted with any combination of from 1 to 6 groups R 11 ;
R 11 is halogen, cyano, nitro, hydroxy, mercapto, amino, formyl, C 1 -C 10 -alkylcarbonyl, C 1 -C 10 -alkoxy, C 2 -C 10 -alkenyloxy, C 2 -C 10 -alkynyloxy, C 1 -C 10 -haloalkoxy, C 3 -C 10 -haloalkenyloxy, C 3 -C 10 -haloalkynyloxy, C 3 -C 8 -cycloalkoxy, C 4 -C 8 -cycloalkenyloxy, C 3 -C 8 -halocycloalkoxy, C 4 -C 8 -halocycloalkenyloxy, C 3 -C 8 -cycloalkyl-C 1 -C 4 -alkoxy, C 4 -C 8 -cycloalkenyl-C 1 -C 4 -alkoxy, C 3 -C 8 -cycloalkyl-C 2 -C 4 -alkenyloxy, C 4 -C 8 -cycloalkenyl-C 2 -C 4 -alkenyloxy, C 1 -C 10 -alkyl-C 3 -C 8 -cycloalkoxy, C 1 -C 10 -alkenyl-C 3 -C 8 -cycloalkoxy, C 1 -C 10 -alkynyl-C 3 -C 8 -cycloalkoxy, C 1 -C 10 -alkyl-C 3 -C 8 -cycloalkenyloxy, C 1 -C 10 -alkenyl-C 3 -C 8 -cycloalkenyloxy, C 1 -C 4 -alkoxy-C 1 -C 10 -alkoxy, C 1 -C 4 -alkoxy-C 2 -C 10 -alkenyloxy, mono- or di(C 1 -C 10 -alkyl)carbamoyl, mono- or di(C 1 -C 10 -haloalkyl)carbamoyl, mono- or di(C 3 -C 8 -cycloalkyl)carbamoyl, C 1 -C 10 -alkoxycarbonyl, C 3 -C 8 -cycloalkoxycarbonyl, C 1 -C 10 -alkylcarbonyloxy, C 3 -C 8 -cyclo alkylcarbonyloxy, C 1 -C 10 -haloalkoxycarbonyl, C 1 -C 10 -haloalkylcarbonyloxy, C 1 -C 10 -alkanamido, C 1 -C 10 -haloalkanamido, C 2 -C 10 -alkenamido, C 3 -C 8 -cycloalkanamido, C 3 -C 8 -cycloalkyl-C 1 -C 4 -alkanamido, alkylthio, C 2 -C 10 -alkenylthio, C 2 -C 10 -alkynylthio, C 1 -C 10 -haloalkylthio, C 2 -C 10 -haloalkenylthio, C 2 -C 10 -haloalkynylthio, C 3 -C 8 -cycloalkylthio, C 3 -C 8 -cycloalkenylthio, C 3 -C 8 -halocycloalkylthio, C 3 -C 8 -halocycloalkenylthio, C 3 -C 8 -cycloalkyl-C 1 -C 4 -alkylthio, C 4 -C 8 -cycloalkenyl-C 1 -C 4 -alkylthio, C 3 -C 8 -cycloalkyl-C 2 -C 4 -alkenylthio, C 4 -C 8 -cycloalkenyl-C 2 -C 4 -alkenylthio, C 1 -C 10 -alkyl-C 3 -C 8 -cycloalkylthio, C 1 -C 10 -alkenyl-C 3 -C 8 -cycloalkylthio, C 1 -C 10 -alkynyl-C 3 -C 8 -cycloalkylthio, C 1 -C 10 -alkyl-C 3 -C 8 -cycloalkenylthio, C 1 -C 10 -alkenyl-C 3 -C 8 -cycloalkenylthio, C 1 -C 10 -alkylsulfinyl, C 2 -C 10 -alkenylsulfinyl, C 2 -C 10 -alkynylsulfinyl, C 1 -C 10 -haloalkylsulfinyl, C 2 -C 10 -haloalkenylsulfinyl, C 2 -C 10 -haloalkynylsulfinyl, C 3 -C 8 -cycloalkylsulfinyl, C 3 -C 8 -cycloalkenylsulfinyl, C 3 -C 8 -halocycloalkylsulfinyl, C 3 -C 8 -halocycloalkenylsulfinyl, C 3 -C 8 -cycloalkyl-C 1 -C 4 -alkylsulfinyl, C 4 -C 8 -cycloalkenyl-C 1 -C 4 -alkylsulfinyl, C 3 -C 8 -cycloalkyl-C 2 -C 4 -alkenylsulfinyl, C 4 -C 8 -cycloalkenyl-C 2 -C 4 -alkenylsulfinyl, C 1 -C 10 -alkyl-C 3 -C 8 -cycloalkylsulfinyl, C 1 -C 10 -alkenyl-C 3 -C 8 -cycloalkylsulfinyl, C 1 -C 10 -alkynyl-C 3 -C 8 -cycloalkylsulfinyl, C 1 -C 10 -alkyl-C 3 -C 8 -cycloalkenylsulfinyl, C 1 -C 10 -alkenyl-C 3 -C 8 -cycloalkenylsulfinyl, C 1 -C 10 -alkylsulfonyl, C 2 -C 10 -alkenylsulfonyl, C 2 -C 10 -alkynylsulfonyl, C 1 -C 10 -haloalkylsulfonyl, C 2 -C 10 -haloalkenylsulfonyl, C 2 -C 10 -haloalkynylsulfonyl, C 3 -C 8 -cycloalkylsulfonyl, C 3 -C 8 -cycloalkenylsulfonyl, C 3 -C 8 -halocycloalkylsulfonyl, C 3 -C 8 -halocycloalkenylsulfonyl, C 3 -C 8 -cycloalkyl-C 1 -C 4 -alkylsulfonyl, C 4 -C 8 -cycloalkenyl-C 1 -C 4 -alkylsulfonyl, C 3 -C 8 -cycloalkyl-C 2 -C 4 -alkenylsulfonyl, C 4 -C 8 -cycloalkenyl-C 2 -C 4 -alkenylsulfonyl, C 1 -C 10 -alkyl-C 3 -C 8 -cycloalkylsulfonyl, C 1 -C 10 -alkenyl-C 3 -C 8 -cycloalkylsulfonyl, C 1 -C 10 -alkynyl-C 3 -C 8 -cycloalkylsulfonyl, C 1 -C 10 -alkyl-C 3 -C 8 -cycloalkenylsulfonyl, C 1 -C 10 -alkenyl-C 3 -C 8 -cycloalkenylsulfonyl, di(C 1 -C 10 -alkyl)amino, C 1 -C 10 -alkylamino, C 2 -C 10 -alkenylamino, C 2 -C 10 -alkynylamino, C 1 -C 10 alkyl-C 2 -C 10 -alkenylamino, C 1 -C 10 -alkyl-C 2 -C 10 -alkynylamino, C 1 -C 10 -haloalkylamino, C 2 -C 10 -haloalkenylamino, C 2 -C 10 -haloalkynylamino, C 3 -C 8 -cycloalkylamino, C 3 -C 8 -cycloalkenylamino, C 3 -C 8 -halocycloalkylamino, C 3 -C 8 -halocycloalkenylamino, C 3 -C 8 -cycloalkyl-C 1 -C 4 -alkylamino, C 4 -C 8 -cycloalkenyl-C 1 -C 4 -alkylamino, C 3 -C 8 -cycloalkyl-C 2 -C 4 -alkenylamino, C 4 -C 8 -cycloalkenyl-C 2 -C 4 -alkenylamino, C 1 -C 10 -alkyl-C 3 -C 8 -cycloalkylamino, C 1 -C 10 -alkenyl-C 3 -C 8 -cycloalkylamino, C 1 -C 10 -alkynyl-C 3 -C 8 -cycloalkylamino, C 1 -C 10 -alkyl-C 3 -C 8 -cycloalkenylamino, C 1 -C 10 -alkenyl-C 3 -C 8 -cycloalkenylamino, aryl, aryloxy, arylthio, arylamino, aryl-C 1 -C 4 -alkoxy, aryl-C 3 -C 4 -alkenyloxy, aryl-C 2 -C 4 -alkenylthio, aryl-C 1 -C 4 -alkylamino, aryl-C 3 -C 4 -alkenylamino, aryl-di(C 1 -C 4 -alkyl)silyl, triarylsilyl,
wherein aryl is phenyl, naphthyl or biphenyl, 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 said aryl and heteroatom cyclic ringsystems are unsubstituted or substituted with any combination of from 1 to 6 groups selected from halogen, cyano, nitro, amino, hydroxy, mercapto, C 1 -C 4 -alkyl, C 3 -C 8 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, di(C 1 -C 4 -alkyl)amino, C 1 -C 4 -haloalkylamino, formyl and C 1 -C 4 -alkylcarbonyl;
Q 1 is hydrogen, halogen, cyano, C 1 -C 4 -alkyl, or C 1 -C 4 -haloalkyl;
Q 2 is halogen, cyano, C 1 -C 4 -alkyl, or C 1 -C 4 -haloalkyl;
Q 3 is halogen, C 1 -C 4 -haloalkyl, or C 1 -C 4 -haloalkoxy;
Q 4 is halogen or C 1 -C 4 -haloalkyl and is in the ortho-position; and
each of X and Y is oxygen;
each of V and V′ is CH;
W is N; and
p is 1;
or the enantiomers or salts or N-oxides thereof.
2. The compound of claim 1 , where R 2 and R 3 each independently are phenyl, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, or C 2 -C 6 -alkynyl, which are unsubstituted or substituted with any combination of 1 to 6 groups selected from halogen and cyano.
3. The compound of claim 1 , where R 2 and R 3 each independently are C 1 -C 4 -alkyl, phenylmethyl, allylmethyl, propargylmethyl, or together with the sulfur atom to which they are attached form a 3- to 6-membered saturated ring which contains 1 to 3 heteroatoms selected from sulfur and oxygen.
4. The compound of claim 1 , which is of the formula I.A
wherein Q′ and Q 3 are as defined in claim 1 .
5. The compound of claim 1 , which is of the formula I.3
where, Q 1 , Q 3 , R 2 and R 3 are as defined in each of rows 1 to 68 of the following table:
Q 1
Q 3
R 2
R 3
1
Cl
CF 3
i-C 3 H 7
i-C 3 H 7
2
H
Br
CH 3
CH 3
3
Cl
Br
CH 2 CH 3
CH 2 CH 3
4
Cl
Br
CH 3
CH 3
5
Cl
Br
i-C 3 H7
i-C 3 H 7
6
Cl
CF 3
i-C 3 H 7
i-C 3 H 7
7
H
Br
CH 3
CH 3
8
Cl
CF 3
CH 3
CH 3
9
H
Br
n-C 3 H 7
CH 3
10
H
CF 3
n-C 3 H 7
CH 3
11
Cl
Br
n-C 3 H 7
CH 3
12
Cl
Br
n-C 5 H 11
CH 2 CH 2 OH
13
H
Br
n-C 5 H 11
CH 2 CH 2 OH
14
Cl
CF 3
CH 3
n-C 3 H 7
15
I
CF 3
CH 3
n-C 3 H 7
16
I
Br
CH 3
n-C 3 H 7
17
H
CF 3
n-C 5 H 11
CH 2 CH 2 OH
18
I
Br
n-C 5 H 11
CH 2 CH 2 OH
19
I
Br
i-C 3 H 7
i-C 3 H 7
20
I
CF 3
i-C 3 H 7
i-C 3 H 7
21
H
Br
i-C 3 H 7
i-C 3 H 7
22
I
Br
CH 3
CH 3
23
I
CF 3
CH 3
CH 3
24
H
CF 3
CH 3
CH 3
25
Cl
Br
CH 2 CH 3
CH 3
26
H
Br
CH 2 CH 3
CH 3
27
I
Br
CH 2 CH 3
CH 3
28
Cl
CF 3
CH 2 CH 3
CH 3
29
H
CF 3
CH 3
CH 2 CH 3
30
I
CF 3
CH 2 CH 3
CH 3
31
H
CF 3
i-C 3 H 7
i-C 3 H 7
32
Cl
CF 3
n-C 5 H 11
CH 2 CH 2 OH
33
I
CF 3
n-C 5 H 11
CH 2 CH 2 OH
34
Cl
CF 3
CH 3
p-F—C 6 H 4
35
Cl
Br
CH 3
p-F—C 6 H 4
36
H
Br
CH 3
p-F—C 6 H 4
37
H
CF 3
CH 3
p-F—C 6 H 4
38
I
CF 3
CH 3
p-F—C 6 H 4
39
I
Br
CH 3
p-F—C 6 H 4
40
Cl
Br
CH 2 CH 2 Cl
CH 2 CH 3
41
Cl
Br
CH 2 CH 3
CHCH 2
42
H
Br
CH 2 CH 3
CHCH 2
43
I
Br
CH 2 CH 3
CHCH 2
44
I
Br
CH 2 CH 2 Cl
CH 2 CH 3
45
Cl
OCH 2 CCH
i-C 3 H 7
i-C 3 H 7
46
I
OCH 2 CCH
i-C 3 H 7
i-C 3 H 7
47
Cl
OCH 2 CCH
CH 3
p-F—C 6 H 4
48
I
OCH 2 CCH
CH 3
p-F—C 6 H 4
49
Cl
OCH 2 CCH
CH 2 CH 2 OH
n-C 5 H 11
50
I
OCH 2 CCH
CH 2 CH 2 OH
n-C 5 H 11
51
H
CF 3
CH 2 CH 3
CH 2 CH 2 Cl
52
I
CF 3
CH 2 CH 2 Cl
CH 2 CH 3
53
CN
CF 3
n-C 3 H 7
CH 3
54
CN
CF 3
p-F—C 6 H 4
CH 3
55
CN
CF 3
CH 3
CH 3
56
CN
Br
n-C 3 H 7
CH 3
57
CN
Br
p-F—C 6 H 4
CH 3
58
CN
Br
n-C 5 H 11
CH 2 CH 2 OH
59
CN
Br
i-C 3 H 7
i-C 3 H 7
60
CN
Br
CH 3
CH 3
61
CN
Br
CH 2 CH 3
CH 3
62
CN
Br
CH 2 CH 3
CHCH 2
63
CN
Br
CH 3
s-C 4 H 9
64
CN
CF 3
CH 2 CH 3
CHCH 2
65
CN
CF 3
CH 3
CH 2 CH 3
66
CN
CF 3
CH 2 CH 2 OH
n-C 5 H 11
67
CN
CF 3
s-C 4 H 9
CH 3
68
CN
CF 3
i-C 3 H 7
i-C 3 H 7 .
6. The compound of claim 1 , which is of the formula I.4
wherein, Q 1 , Q 3 , and the radical S[O] n R 2 R 3 are as defined in each of rows 1 to 23 of the following table:
Q 1
Q 3
S[O] n R 2 R 3
1
Cl
Br
2
I
Br
3
I
CF 3
4
H
CF 3
5
Cl
CF 3
6
Cl
Br
7
I
Br
8
H
CF 3
9
H
Br
10
I
CF 3
11
I
CF 3
12
Cl
Br
13
I
Br
14
Cl
OCH 2 CCH
15
Cl
OCH 2 CCH
16
CN
CF 3
17
CN
Br
18
CN
Br
19
CN
Br
20
CN
CF 3
21
CN
CF 3
22
Cl
Br
23
Cl
CF 3
[CH 2 CH 2 OH][(CH 2 ) 4 CH 3 ]S(═O)—.
7. A method for controlling insects, acarids or nematodes comprising, contacting said insect, acarid or nematode or their food supply, habitat, breeding ground or their locus with a pesticidally effective amount of one or more compounds of claim 1 .
8. The method of claim 7 , wherein R 2 and R 3 each independently are phenyl, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, or C 2 -C 6 -alkynyl, which are unsubstituted or substituted with any combination of 1 to 6 groups selected from halogen and cyano.
9. The method of claim 7 , wherein R 2 and R 3 each independently are C 1 -C 4 -alkyl, phenylmethyl, allylmethyl, propargylmethyl, or together with the sulfur atom to which they are attached form a 3- to 6-membered saturated ring which contains 1 to 3 heteroatoms selected from sulfur and oxygen.
10. The method of claim 7 , wherein the compound is of the formula I.A.
11. The method of claim 7 , wherein the compound is of the formula I.3
where, Q 1 , Q 3 , R 2 and R 3 are as defined in each of rows 1 to 68 of the following table:
Q 1
Q 3
R 2
R 3
69
Cl
CF 3
i-C 3 H 7
i-C 3 H 7
70
H
Br
CH 3
CH 3
71
Cl
Br
CH 2 CH 3
CH 2 CH 3
72
Cl
Br
CH 3
CH 3
73
Cl
Br
i-C 3 H7
i-C 3 H 7
74
Cl
CF 3
i-C 3 H 7
i-C 3 H 7
75
H
Br
CH 3
CH 3
76
Cl
CF 3
CH 3
CH 3
77
H
Br
n-C 3 H 7
CH 3
78
H
CF 3
n-C 3 H 7
CH 3
79
Cl
Br
n-C 3 H 7
CH 3
80
Cl
Br
n-C 5 H 11
CH 2 CH 2 OH
81
H
Br
n-C 5 H 11
CH 2 CH 2 OH
82
Cl
CF 3
CH 3
n-C 3 H 7
83
I
CF 3
CH 3
n-C 3 H 7
84
I
Br
CH 3
n-C 3 H 7
85
H
CF 3
n-C 5 H 11
CH 2 CH 2 OH
86
I
Br
n-C 5 H 11
CH 2 CH 2 OH
87
I
Br
i-C 3 H 7
i-C 3 H 7
88
I
CF 3
i-C 3 H 7
i-C 3 H 7
89
H
Br
i-C 3 H 7
i-C 3 H 7
90
I
Br
CH 3
CH 3
91
I
CF 3
CH 3
CH 3
92
H
CF 3
CH 3
CH 3
93
Cl
Br
CH 2 CH 3
CH 3
94
H
Br
CH 2 CH 3
CH 3
95
I
Br
CH 2 CH 3
CH 3
96
Cl
CF 3
CH 2 CH 3
CH 3
97
H
CF 3
CH 3
CH 2 CH 3
98
I
CF 3
CH 2 CH 3
CH 3
99
H
CF 3
i-C 3 H 7
i-C 3 H 7
100
Cl
CF 3
n-C 5 H 11
CH 2 CH 2 OH
101
I
CF 3
n-C 5 H 11
CH 2 CH 2 OH
102
Cl
CF 3
CH 3
p-F—C 6 H 4
103
Cl
Br
CH 3
p-F—C 6 H 4
104
H
Br
CH 3
p-F—C 6 H 4
105
H
CF 3
CH 3
p-F—C 6 H 4
106
I
CF 3
CH 3
p-F—C 6 H 4
107
I
Br
CH 3
p-F—C 6 H 4
108
Cl
Br
CH 2 CH 2 Cl
CH 2 CH 3
109
Cl
Br
CH 2 CH 3
CHCH 2
110
H
Br
CH 2 CH 3
CHCH 2
111
I
Br
CH 2 CH 3
CHCH 2
112
I
Br
CH 2 CH 2 Cl
CH 2 CH 3
113
Cl
OCH 2 CCH
i-C 3 H 7
i-C 3 H 7
114
I
OCH 2 CCH
i-C 3 H 7
i-C 3 H 7
115
Cl
OCH 2 CCH
CH 3
p-F—C 6 H 4
116
I
OCH 2 CCH
CH 3
p-F—C 6 H 4
117
Cl
OCH 2 CCH
CH 2 CH 2 OH
n-C 5 H 11
118
I
OCH 2 CCH
CH 2 CH 2 OH
n-C 5 H 11
119
H
CF 3
CH 2 CH 3
CH 2 CH 2 Cl
120
I
CF 3
CH 2 CH 2 Cl
CH 2 CH 3
121
CN
CF 3
n-C 3 H 7
CH 3
122
CN
CF 3
p-F—C 6 H 4
CH 3
123
CN
CF 3
CH 3
CH 3
124
CN
Br
n-C 3 H 7
CH 3
125
CN
Br
p-F—C 6 H 4
CH 3
126
CN
Br
n-C 5 H 11
CH 2 CH 2 OH
127
CN
Br
i-C 3 H 7
i-C 3 H 7
128
CN
Br
CH 3
CH 3
129
CN
Br
CH 2 CH 3
CH 3
130
CN
Br
CH 2 CH 3
CHCH 2
131
CN
Br
CH 3
s-C 4 H 9
132
CN
CF 3
CH 2 CH 3
CHCH 2
133
CN
CF 3
CH 3
CH 2 CH 3
134
CN
CF 3
CH 2 CH 2 OH
n-C 5 H 11
135
CN
CF 3
s-C 4 H 9
CH 3
136
CN
CF 3
i-C 3 H 7
i-C 3 H 7 .
12. The method of claim 7 , wherein the compound is of the formula I.4
where, Q 1 , Q 3 , and the radical S[O] n R 2 R 3 are as defined in each of rows 1 to 23 of the following table:
Q 1
Q 3
S[O] n R 2 R 3
24
Cl
Br
25
I
Br
26
I
CF 3
27
H
CF 3
28
Cl
CF 3
29
Cl
Br
30
I
Br
31
H
CF 3
32
H
Br
33
I
CF 3
34
I
CF 3
35
Cl
Br
36
I
Br
37
Cl
OCH 2 CCH
38
Cl
OCH 2 CCH
39
CN
CF 3
40
CN
Br
41
CN
Br
42
CN
Br
43
CN
CF 3
44
CN
CF 3
45
Cl
Br
46
Cl
CF 3
[CH 2 CH 2 OH][(CH 2 ) 4 CH 3 ]S(═O)—.
13. A method of protecting growing plants from attack or infestation by insects, acarids or nematodes comprising, applying to the foliage of the plants, or to the soil or water in which said plants are growing a pesticidally effective amount of one or more compounds of claim 1 .
14. The method of claim 13 , wherein R 2 and R 3 each independently are phenyl, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, or C 2 -C 6 -alkynyl, which are unsubstituted or substituted with any combination of 1 to 6 groups selected from halogen and cyano.
15. The method of claim 13 , wherein R 2 and R 3 each independently are C 1 -C 4 -alkyl, phenylmethyl, allylmethyl, propargylmethyl, or together with the sulfur atom to which they are attached form a 3- to 6-membered saturated ring which contains 1 to 3 heteroatoms selected from sulfur and oxygen.
16. The method of claim 13 , wherein the compound is of the formula I.A.
17. The method of claim 13 , wherein the compound is of the formula I.3
where, Q 1 , Q 3 , R 2 and R 3 are as defined in each of rows 1 to 68 of the following table:
Q 1
Q 3
R 2
R 3
137
Cl
CF 3
i-C 3 H 7
i-C 3 H 7
138
H
Br
CH 3
CH 3
139
Cl
Br
CH 2 CH 3
CH 2 CH 3
140
Cl
Br
CH 3
CH 3
141
Cl
Br
i-C 3 H7
i-C 3 H 7
142
Cl
CF 3
i-C 3 H 7
i-C 3 H 7
143
H
Br
CH 3
CH 3
144
Cl
CF 3
CH 3
CH 3
145
H
Br
n-C 3 H 7
CH 3
146
H
CF 3
n-C 3 H 7
CH 3
147
Cl
Br
n-C 3 H 7
CH 3
148
Cl
Br
n-C 5 H 11
CH 2 CH 2 OH
149
H
Br
n-C 5 H 11
CH 2 CH 2 OH
150
Cl
CF 3
CH 3
n-C 3 H 7
151
I
CF 3
CH 3
n-C 3 H 7
152
I
Br
CH 3
n-C 3 H 7
153
H
CF 3
n-C 5 H 11
CH 2 CH 2 OH
154
I
Br
n-C 5 H 11
CH 2 CH 2 OH
155
I
Br
i-C 3 H 7
i-C 3 H 7
156
I
CF 3
i-C 3 H 7
i-C 3 H 7
157
H
Br
i-C 3 H 7
i-C 3 H 7
158
I
Br
CH 3
CH 3
159
I
CF 3
CH 3
CH 3
160
H
CF 3
CH 3
CH 3
161
Cl
Br
CH 2 CH 3
CH 3
162
H
Br
CH 2 CH 3
CH 3
163
I
Br
CH 2 CH 3
CH 3
164
Cl
CF 3
CH 2 CH 3
CH 3
165
H
CF 3
CH 3
CH 2 CH 3
166
I
CF 3
CH 2 CH 3
CH 3
167
H
CF 3
i-C 3 H 7
i-C 3 H 7
168
Cl
CF 3
n-C 5 H 11
CH 2 CH 2 OH
169
I
CF 3
n-C 5 H 11
CH 2 CH 2 OH
170
Cl
CF 3
CH 3
p-F—C 6 H 4
171
Cl
Br
CH 3
p-F—C 6 H 4
172
H
Br
CH 3
p-F—C 6 H 4
173
H
CF 3
CH 3
p-F—C 6 F 4
174
I
CF 3
CH 3
p-F—C 6 H 4
175
I
Br
CH 3
p-F—C 6 H 4
176
Cl
Br
CH 2 CH 2 Cl
CH 2 CH 3
177
Cl
Br
CH 2 CH 3
CHCH 2
178
H
Br
CH 2 CH 3
CHCH 2
179
I
Br
CH 2 CH 3
CHCH 2
180
I
Br
CH 2 CH 2 Cl
CH 2 CH 3
181
Cl
OCH 2 CCH
i-C 3 H 7
i-C 3 H 7
182
I
OCH 2 CCH
i-C 3 H 7
i-C 3 H 7
183
Cl
OCH 2 CCH
CH 3
p-F—C 6 H 4
184
I
OCH 2 CCH
CH 3
p-F—C 6 H 4
185
Cl
OCH 2 CCH
CH 2 CH 2 OH
n-C 5 H 11
186
I
OCH 2 CCH
CH 2 CH 2 OH
n-C 5 H 11
187
H
CF 3
CH 2 CH 3
CH 2 CH 2 Cl
188
I
CF 3
CH 2 CH 2 Cl
CH 2 CH 3
189
CN
CF 3
n-C 3 H 7
CH 3
190
CN
CF 3
p-F—C 6 H 4
CH 3
191
CN
CF 3
CH 3
CH 3
192
CN
Br
n-C 3 H 7
CH 3
193
CN
Br
p-F—C 6 H 4
CH 3
194
CN
Br
n-C 5 H 11
CH 2 CH 2 OH
195
CN
Br
i-C 3 H 7
i-C 3 H 7
196
CN
Br
CH 3
CH 3
197
CN
Br
CH 2 CH 3
CH 3
198
CN
Br
CH 2 CH 3
CHCH 2
199
CN
Br
CH 3
s-C 4 H 9
200
CN
CF 3
CH 2 CH 3
CHCH 2
201
CN
CF 3
CH 3
CH 2 CH 3
202
CN
CF 3
CH 2 CH 2 OH
n-C 5 H 11
203
CN
CF 3
s-C 4 H 9
CH 3
204
CN
CF 3
i-C 3 H 7
i-C 3 H 7 .
18. The method of claim 13 , wherein the compound is of the formula I.4
where, Q 1 , Q 3 , and the radical S[O] n R 2 R 3 are as defined in each of rows 1 to 23 of the following table:
Q 1
Q 3
S[O] n R 2 R 3
47
Cl
Br
48
I
Br
49
I
CF 3
50
H
CF 3
51
Cl
CF 3
52
Cl
Br
53
I
Br
54
H
CF 3
55
H
Br
56
I
CF 3
57
I
CF 3
58
Cl
Br
59
I
Br
60
Cl
OCH 2 CCH
61
Cl
OCH 2 CCH
62
CN
CF 3
63
CN
Br
64
CN
Br
65
CN
Br
66
CN
CF 3
67
CN
CF 3
68
Cl
Br
69
Cl
CF 3
[CH 2 CH 2 OH]](CH 2 ) 4 CH 3 ]S(═O)—.
19. A method for treating an animal infected by parasites or controlling or protecting the animal against infestation or infection by parasites comprising, administering orally, topically or parenterally, or applying to said animal a parasiticidally effective amount of one or more compounds of claim 1 .